Compound inhibiting in vivo phosphorous transport and medicine containing the same

Abstract

An objective of the present invention is to provide compounds that can effectively suppress the concentration of phosphorus in serum to effectively prevent or treat diseases induced by an increase in concentration of phosphate in serum. The compounds according to the present invention are compounds represented by formula (I) and pharmaceutically acceptable salts and solvates thereof: wherein A represents an optionally substituted five- to nine-membered unsaturated carbocyclic moiety or a five- to nine-membered unsaturated heterocyclic moiety, and represents a single bond or a double bond, R5 represents optionally substituted aryl or the like, Z represents —N═CHR6R7 or the like, R6 and R7 represent H, optionally substituted alkyl, optionally substituted aryl or the like, R101 and R102 together form ═O, and R103 and R104 represent H, or R101 and R104 together from a bond, and R102 and R103 together form a bond.

Description

BACKGROUND OF THE INVENTION

1. Field of the Invention

The present invention relates to compounds capable of suppressing the phosphate concentration of serum, and more particularly to compounds useful for the prevention and treatment of hyperphosphatemia.

2. Related Art

The phosphate concentration of serum is specified by balance between absorption of phosphate from the intestine, intracellular and bone accumulation, filtration into primitive urine in the kidney, and subsequent reabsorption in uriniferous tubules. When the phosphate concentration of serum is not less than 5.0 mg/dl, this condition is called hyperphosphatemia and is a clinical condition that significantly appears mainly in end-stage renal failure and dialysis patients. This is mainly induced by deteriorated excretion of phosphate involved in elimination of renal function. It is also suggested that an increase in phosphate absorption from the intestine derived from the administration of vitamin D participates in this clinical condition. The hyperphosphatemia secondarily leads to hypocalcemia and thus induces secondary hyperparathyroidism which is in turn a principal factor for renal osteodystrophy.

In the prior art technique, to alleviate these clinical conditions, ingestion of a diet having a low phosphate content and the use of a phosphate adsorbent having the function of adsorbing phosphate in the diet have been carried out from the viewpoint of reducing the absorption of phosphate from the intestine. However, it has been pointed out that the diet having a low phosphate content is disadvantageous in that a nutritional disorder is likely to occur, for example, due to lack of ingestion of other nutriments, or observance of this dietary is difficult because the taste is not good. Representative examples of oral phosphate adsorbents include calcium preparations, magnesium preparations, and aluminum preparations. However, it has been pointed out, for example, that the calcium preparations and the magnesium preparations induce hypercalcemia and hypermagnesemia, respectively, and the aluminum preparations induce aluminum osteopathy, aluminum cerebropathy, and dialysis dementia. In recent years, various anion exchange resins have been developed as the oral phosphate adsorbent. Since, however, these anion exchange resins have lower phosphate adsorption capacity than the above group of compounds, a high level of dosage is necessary for phosphate absorption reduction purposes. Therefore, it cannot be said that the compliance for patients is good.

Despite the fact that all the conventional therapeutic agents for hyperphosphatemia suffer from the above problems, up to now, therapeutic agents for hyperphosphatemia which can solve the above problems have not been reported.

Therapeutic agents for hyperphosphatemia are disclosed, for example, in WO 98/03185 and Kidney and Metabolic Bone Diseases, Vol. 15, No. 1 pp 75-80 (2002).

SUMMARY OF THE INVENTION

The present inventors have now found compounds that can inhibit sodium-dependent phosphate transport into rabbit jejunal brush border membrane vesicle (hereinafter referred to as “rabbit BBMV”) and can inhibit sodium-dependent phosphate uptake in Xenopus oocytes, which express sodium-dependent phosphate absorption carrier (NaPi-2a and NaPi-2b), present in the kidney and the small intestine, on cell membranes. The present inventors have also found that compounds having a hydrazine skeleton can lower blood radioactivity of normal rats to which diets containing ³²P, a radioisotope, have been administered orally.

An object of the present invention is to provide compounds and pharmaceutical compositions that can effectively prevent or treat diseases induced by an increase in the phosphate concentration of serum by effectively suppressing the phosphate concentration of serum through a mechanism different from the conventional mechanism.

According to the present invention, there are provided compounds represented by formula (I) and pharmaceutically acceptable salts and solvates thereof: wherein

A represents a five- to nine-membered unsaturated carbocyclic moiety or a five- to nine-membered unsaturated heterocyclic moiety, and represents a single bond or a double bond,

the carbocyclic moiety and heterocyclic moiety represented by A are optionally substituted by

(a) a halogen atom;

(b) hydroxyl;

(c) C_1-6 alkyl;

(d) C_1-6 alkoxy;

(e) aryl;

(f) aryloxy;

(g) arylthio;

(h) alkylthio;

(i) nitro;

(j) amino;

(k) mono- or di-arylamino;

(l) mono- or di-C_1-6 alkylamino;

(m) C_2-6 alkenyl;

(n) C_2-6 alkenyloxy;

(o) C_2-6 alkenylthio;

(p) mono- or di-C_2-6 alkenylamino;

(q) carboxyl; or

(r) C_1-6 alkyl- or aryl-oxycarbonyl;

(c) the C_1-6 alkyl group, (d) the C_1-6 alkoxy group, (e) the aryl group, (f) the aryloxy group, (g) the arylthio group, (h) the alkylthio group, (m) the C_2-6 alkenyl group, (n) the C_2-6 alkenyloxy group, and (o) the C_2-6 alkenylthio group are optionally substituted by (1) hydroxyl, (2) thiol, (3) amino, (4) C_1-6 alkoxy, (5) C_1-6 alkylthio, (6) C_1-6 alkylsulfonyl, (7) mono- or di-C_1-6 alkylamino in which the di-C_1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms, (8) aryloxy, (9) arylthio, (10) arylsulfonyl, (11) aryl, (12) a heterocyclic group, (13) a halogen atom, (14) arylamino in which the amino group is optionally substituted by C_1-6 alkyl, and the aryl group is optionally substituted by halogen, C_1-6 alkyl, C_1-6 alkoxy, or C_1-6 alkylamino, (15) C_1-6 alkoxy-(CH₂CH₂O)m wherein m is an integer of 1 to 6, (16) carboxyl, (17) an oxygen atom (═O), or (18) C_3-7 cycloalkyl,

the aryl moiety in (k) the mono- or di-arylamino group is optionally substituted by (1) hydroxyl, (2) thiol, (3) amino, (4) C_1-6 alkoxy, (5) C_1-6alkylthio, (6) C_1-6 alkylsulfonyl, (7) mono- or di-C_1-6 alkylamino in which the di-C_1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms, (8) aryloxy, (9) arylthio, (10) arylsulfonyl, (11) aryl, (12) a heterocyclic group, (13) a halogen atom, (14) arylamino in which the amino group is optionally substituted by C_1-6 alkyl, and the aryl group is optionally substituted by halogen, C_1-6 alkyl, C_1-6 alkoxy, or C_1-6 alkylamino, (15) C_1-6 alkoxy-(CH₂CH₂O)m wherein m is an integer of 1 to 6, (16) carboxyl, (17) an oxygen atom (═O), or (18) C_3-7 cycloalkyl, and, in the case of the mono-arylamino group, the amino group is optionally substituted by C_1-6 alkyl optionally substituted by hydroxyl or a halogen atom,

in (l) the mono- or di-C_1-6 alkylamino, the di-C_1-6 alkyl group may form cyclic amino optionally containing 1 to 3 heteroatoms, and one or two alkyl groups on the amino group and the cyclic amino moiety are optionally substituted by a halogen atom; C_1-6 alkyl optionally substituted by hydroxyl, a halogen atom, or aryl optionally substituted by a halogen atom, C_1-6 alkyl, or C_1-6 alkyloxy, a heterocyclic group optionally substituted by a halogen atom, C_1-6 alkyl, or C_1-6 alkyloxy, and, when one or two alkyl groups on the amino group and the cyclic amino moiety are substituted by two C_1-6 alkyl groups, they together may form C_3-7 cycloalkyl; C_1-6 alkoxy; C_1-6 alkylthio; mono- or di-C_1-6 alkylamino in which the di-C_1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms, and one or two C_1-6 alkyl groups on the amino group and the cyclic amino moiety are optionally substituted by hydroxyl or a halogen atom; arylamino in which the amino group is optionally substituted by C_1-6 alkyl; mono- or di-C_1-6 alkylcarbamoylmethyl in which the di-C_1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms, and one or two alkyl groups on the amino group and the cyclic amino moiety are optionally substituted by hydroxyl; aryloxy; arylthio; an oxygen atom; hydroxyl; carboxyl; C_1-6 alkoxy- or aryloxy-carbonyl; C_1-6 alkylcarbonyl; aryl optionally substituted by a halogen atom or hydroxyl; an oxygen atom (═O); or a heterocyclic group,

in (p) the mono- or di-C_2-6 alkenylamino group, the amino group of the monoalkenylamino group is optionally substituted by C_1-6 alkyl optionally substituted by hydroxyl or a halogen atom, and the di-C_2-6 alkenyl together may form unsaturated cyclic amino optionally containing 1 to 3 heteroatoms, and one or two alkenyl groups on the amino group or the unsaturated cyclic amino moiety are optionally substituted by a halogen atom; C_1-6 alkyl optionally substituted by hydroxyl, a halogen atom, aryl optionally substituted by a halogen atom, C_1-6 alkyl, or C_1-6 alkyloxy, a heterocyclic group optionally substituted by a halogen atom, C_1-6 alkyl, or C_1-6 alkyloxy, and, when one or two alkyl groups on the amino group and the cyclic amino moiety are substituted by two C_1-6 alkyl groups, they together may form C_3-7 cycloalkyl; C_1-6 alkoxy; C_1-6 alkylthio; mono- or di-C_1-6 alkylamino in which the di-C_1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms, and one or two C_1-6 alkyl groups on the amino group and the cyclic amino moiety are optionally substituted by hydroxyl or a halogen atom; arylamino in which the amino group is optionally substituted by C_1-6 alkyl; mono- or di-C_1-6 alkylcarbamoylmethyl in which the di-C_1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms, and one or two alkyl groups on the amino group and the cyclic amino moiety are optionally substituted by hydroxyl; aryloxy; arylthio; an oxygen atom; hydroxyl; carboxyl; C_1-6 alkoxy- or aryloxy-carbonyl; C_1-6 alkylcarbonyl; aryl optionally substituted by a halogen atom or hydroxyl; an oxygen atom (═O); or a heterocyclic group,

when the carbocyclic moiety and hetrocyclic moiety represented by A are substituted by two (c) C_1-6 alkyl groups or (m) C_2-6 alkenyl groups, the alkyl or alkenyl groups together with the carbon atoms to which they are respectively attached may form an unsaturated five- to seven-membered carbocyclic ring,

R⁵ represents C_1-6 alkyl, aryl, C_1-6 alkoxy, aryloxy, C_1-6 alkylamino, arylamino, C_1-6 alkylthio, arylthio, C_3-7 cycloalkyl, or a heterocyclic group, and the C_1-6 alkyl, aryl, C_1-6 alkoxy, aryloxy, C_1-6 alkylamino, arylamino, C_1-6 alkylthio, arylthio, C_3-7 cycloalkyl, or heterocyclic group represented by R⁵ may be the same or different, and is optionally substituted by

(I) a halogen atom;

(II) C_1-6 alkyl optionally containing a substituent selected from the group consisting of (1) hydroxyl, (2) thiol, (3) amino, (4) C_1-6 alkoxy, (5) C_1-6 alkylthio, (6) C_1-6 alkylsulfinyl, (7) C_1-6 alkylsulfonyl, (8) mono- or di-C_1-6 alkylamino, (8′) amino substituted by a heterocyclic group optionally substituted by C_1-6 alkyl, (9) C_1-6 alkylcarbonyloxy, (10) C_1-6 alkylcarbonylthio, (11) C_1-6 alkylcarbonylamino, (12) aryloxy, (13) arylthio, (14) arylsulfinyl, (15) arylsulfonyl, (16) arylamino, (17) C_1-6 alkyl- or aryl-sulfonylamino, (18) C_1-6 alkyl- or aryl-ureido, (19) C_1-6 alkoxy- or aryloxy-carbonylamino, (20) C_1-6 alkylamino- or arylamino-carbonyloxy, (21) carboxyl, (22) nitro, (23) a heterocyclic group, (23′) Het-S(═O)j- wherein Het represents a heterocyclic group, j is 0, 1, or 2, and Het is optionally substituted by alkyl optionally substituted by mono- or di-C_1-6 alkylamino in which the di-C_1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms and one or two alkyl groups on the amino group and the cyclic amino moiety are optionally substituted by hydroxyl, (24) cyano, and (25) a halogen atom,

wherein the alkyl moiety in (4) the C_1-6 alkoxy group, (5) the C_1-6 alkylthio group, (6) the C_1-6 alkylsulfinyl group, and (7) the C_1-6 alkylsulfonyl group is optionally substituted by a halogen atom; C_1-6 alkyl; C_1-6 alkoxy; C_1-6 alkylthio; mono- or di-C_1-6 alkylamino in which the di-C_1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms; aryloxy; arylthio; hydroxyl; carboxyl; —S(═O)₂(—OH); C_1-6 alkoxy- or aryloxy-carbonyl; C_1-6 alkylcarbonyl; aryl; or a heterocyclic group optionally substituted by alkyl optionally substituted by mono- or di-C_1-6 alkylamino in which the di-C_1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms, and one or two alkyl groups on the amino group and cyclic amino moiety are optionally substituted by hydroxy, and

in (8) the mono- or di-C_1-6 alkylamino group, the di-C_1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms, and one or two alkyl groups on the amino group and the cyclic amino moiety are optionally substituted by a halogen atom; C_1-6 alkyl optionally substituted by hydroxyl, a halogen atom, aryl optionally substituted by a halogen atom, C_1-6 alkyl, or C_1-6 alkyloxy, or a heterocyclic group optionally substituted by a halogen atom, C_1-6 alkyl, or C_1-6 alkyloxy, and, when one or two alkyl groups on the amino group and the cyclic amino moiety are substituted by two C_1-6 alkyl groups, they together may form C_3-7 cycloalkyl; C_1-6 alkoxy; C_1-6 alkylthio; mono- or di-C_1-6 alkylamino in which the di-C_1-6 alkylamino may form cyclic amino optionally containing 1 to 3 heteroatoms, and one or two alkyl groups on the amino group and the cyclic amino moiety are optionally substituted by hydroxyl; arylamino in which the amino group is optionally substituted by C_1-6 alkyl; mono- or di-C_1-6 alkylcarbamoylmethyl in which the di-C_1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms, and one or two alkyl groups on the amino group and the cyclic amino moiety are optionally substituted by hydroxyl; aryloxy; arylthio; an oxygen atom (═O); hydroxyl; carboxyl; C_1-6 alkoxy- or aryloxy-carbonyl; C_1-6 alkylcarbonyl; aryl optionally substituted by a halogen atom or hydroxyl; or a heterocyclic group, preferably a five- to seven-membered saturated or unsaturated heterocyclic ring, more preferably pyridyl, pyrimidyl, or pyridazyl, and, when one carbon atom in the cyclic amino moiety is substituted by two C_1-6 alkoxy groups which may be the same or different, the two alkoxy groups together may form group —O—(CH₂)p-O— wherein p is an integer of 2 to 4, and the cyclic amino group may condense with a monocyclic or bicyclic aromatic carbocyclic ring, preferably phenyl or naphthyl, or a monocyclic or bicyclic aromatic heterocyclic ring, preferably pyridyl or naphthyridyl to represent a bicyclic or tricyclic heterocyclic group;

(III) C_1-6 alkoxy optionally substituted by a halogen atom;

(IV) C_1-6 alkylthio optionally substituted by a halogen atom;

(V) C_3-7 cycloalkyl;

(VI) aryl;

(VII) aryloxy;

(VIII) C_1-6 alkylcarbonylamino;

(VIX) C_1-6 alkylcarbonyloxy;

(X) hydroxyl;

(XI) nitro;

(XII) cyano;

(XIII) amino;

(XIV) mono- or di-C_1-6 alkylamino in which the di-C_1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms;

(XV) arylamino;

(XVI) C_1-6 alkyl- or aryl-sulfonylamino;

(XVII) C_1-6 alkyl- or aryl-ureido;

(XVIII) C_1-6 alkoxy- or aryloxy-carbonylamino;

(XIX) C_1-6 alkylamino- or arylamino-carbonyloxy;

(XX) C_1-6 alkoxy- or aryloxy-carbonyl;

(XXI) acyl;

(XXII) carboxyl;

(XXIII) carbamoyl;

(XXIV) mono- or di-alkylcarbamoyl;

(XXV) a heterocyclic group;

(XXVI) alkyl- or aryl-sulfonyl;

(XXVII) C_2-6 alkenyloxy group; or

(XXVIII) C_2-6 alkynyloxy,

Z represents group (A), group (B), or group (C): wherein

R⁶ and R⁷, which may be the same or different, represent a hydrogen atom, C_1-6 alkyl, C_2-6 alkenyl, C_2-6 alkynyl, aryl, aryl C_1-6 alkyl, aryl C_2-6 alkenyl, or a heterocyclic group, and the C_1-6 alkyl, aryl, aryl C_1-6 alkyl, aryl C_2-6 alkenyl, and heterocyclic groups, which may be the same or different, are optionally substituted by:

(I) a halogen atom;

(II) C_1-6 alkyl optionally having a substituent selected from a group consisting of (1) hydroxyl, (2) thiol, (3) amino, (4) C_1-6 alkoxy, (5) C_1-6 alkylthio optionally substituted by hydroxyl, (6) C_1-6 alkylsulfinyl, (7) C_1-6 alkylsulfonyl, (8) mono- or di-C_1-6 alkylamino in which the di-C_1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms, (9) C_1-6 alkylcarbonyloxy, (10) C_1-6 alkylcarbonylthio, (11) C_1-6 alkylcarbonylamino, (12) aryloxy, (13) arylthio, (14) arylsulfinyl, (15) arylsulfonyl, (16) arylamino, (17) C_1-6 alkyl- or aryl-sulfonylamino, (18) C_1-6 alkyl- or aryl-ureido, (19) C_1-6 alkoxy- or aryloxy-carbonylamino, (20) C_1-6 alkylamino- or arylamino-carbonyloxy, (21) carboxyl, (22) nitro, (23) a heterocyclic group, (23′) Het-S— wherein Het represents a heterocyclic group, (24) cyano, (25) a halogen atom, and (26) C_1-6 alkyl- or aryl-oxycarbonyl;

(III) C_1-6 alkoxy optionally having a substituent selected from the group consisting of (1) hydroxyl, (2) thiol, (3) amino, (4) C_1-6 alkoxy, (5) C_1-6 alkylthio optionally substituted by hydroxyl, (6) C_1-6 alkylsulfinyl, (7) C_1-6 alkylsulfonyl, (8) mono- or di-C_1-6 alkylamino in which the di-C_1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms, (9) C_1-6 alkylcarbonyloxy, (10) C_1-6 alkylcarbonylthio, (11) C_1-6 alkylcarbonylamino, (12) aryloxy, (13) arylthio, (14) arylsulfinyl, (15) arylsulfonyl, (16) arylamino, (17) C_1-6 alkyl- or aryl-sulfonylamino, (18) C_1-6 alkyl- or aryl-ureido, (19) C_1-6 alkoxy- or aryloxy-carbonylamino, (20) C_1-6 alkylamino- or arylamino-carbonyloxy, (21) carboxyl, (22) nitro, (23) a heterocyclic group, (23′) Het-S— wherein Het represents a heterocyclic group, (24) cyano, (25) a halogen atom, and (26) C_1-6 alkyl- or aryl-oxycarbonyl;

(IV) C_1-6 alkylthio optionally substituted by a halogen atom;

(V) C_3-7 cycloalkyl;

(VI) aryl;

(VII) aryloxy;

(VIII) C_1-6 alkylcarbonylamino;

(VIX) C_1-6 alkylcarbonyloxy;

(X) hydroxyl;

(XI) nitro;

(XII) cyano;

(XIII) amino;

(XIV) mono- or di-C_1-6 alkylamino in which the di-C_1-6 alkylamino may form cyclic amino optionally containing 1 to 3 heteroatoms;

(XV) arylamino;

(XVI) C_1-6 alkyl- or aryl-sulfonylamino;

(XVII) C_1-6 alkyl- or aryl-ureido;

(XVIII) C_1-6 alkoxy- or aryloxy-carbonylamino;

(XIX) C_1-6 alkylamino- or arylamino-carbonyloxy;

(XX) C_1-6 alkoxy- or aryloxy-carbonyl;

(XXI) acyl;

(XXII) carboxyl;

(XXIII) carbamoyl;

(XXIV) mono- or di-alkylcarbamoyl;

(XXV) a heterocyclic group;

(XXVI) alkyl- or aryl-sulfonyl;

(XXVII) C_2-6 alkenyloxy; or

(XXVIII) C_2-6 alkynyloxy,

R¹⁷ represents a hydrogen atom,

R¹⁰¹ and R¹⁰² together represent ═O, and R¹⁰³ and R¹⁰⁴ represent a hydrogen atom, or R¹⁰¹ and R¹⁰⁴ together represent a bond, and R¹⁰² and R¹⁰³ together represent a bond.

Compounds according to the present invention include compounds represented by formula (I-3) and pharmaceutically acceptable salts and solvates thereof: wherein R²⁰¹, R²⁰², R²⁰³, R²⁰⁴, R^201′, R^202′, R^203′, and R^204′, which may be the same or different, represent a hydrogen atom, a halogen atom, hydroxyl, C_1-6 alkyl, or C_1-6 alkoxy,

R²⁰⁵ and R^205′, which may be the same or different, represent a hydrogen atom or C_1-6 alkyl,

R²⁰⁶ and R^206′, which may be the same or different, represent group A or group B wherein R⁶ represents a hydrogen atom or C_1-6 alkyl, R⁷ represents aryl or a saturated or unsaturated five- or six-membered heterocyclic group in which the aryl group and heterocyclic group are optionally substituted by a halogen atom or C_1-6 alkyl optionally substituted by a halogen atom, and

T represents C_2-8 alkylene chain.

The pharmaceutical composition according to the present invention comprises the compound according to the present invention.

The pharmaceutical composition according to the present invention may be used for the prevention or treatment of diseases for which serum phosphorus lowering action or phosphate transport inhibition is therapeutically effective. Further, the compounds according to the present invention may be used as a serum phosphorus concentration lowering agent and a phosphate transport inhibitor.

According to the present invention, there is provided use of the compound according to the present invention, for the manufacture of a medicament in the prevention or treatment of diseases for which serum phosphorus lowering action or phosphate transport inhibition is therapeutically effective.

Further, according to the present invention, there is provided use of the compound according to the present invention, for the manufacture of a serum phosphorus concentration lowering agent.

Furthermore, according to the present invention, there is provided use of the compound according to the present invention, for the manufacture of a phosphate transport inhibitor.

Furthermore, according to the present invention, there is provided a method for preventing or treating a disease for which serum phosphorus lowering action or phosphate transport inhibition is therapeutically effective, said method comprising the step of administering a therapeutically or prophylactically effective amount of the compound according to the present invention to a mammal.

Furthermore, according to the present invention, there is provided a method for lowering the concentration of serum phosphorus in a blood stream, said method comprising the step of administering a therapeutically or prophylactically effective amount of the compound according to the present invention to a mammal.

Furthermore, according to the present invention, there is provided a method for inhibiting phosphate transport in vivo, said method comprising the step of administering a therapeutically or prophylactically effective amount of the compound according to the present invention to a mammal.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 shows the inhibition of sodium-dependent phosphate uptake of rabbit jejunal brush border membrane vesicle by compounds according to the present invention;

FIG. 2 shows the inhibition of sodium-dependent glucose uptake of rabbit jejunal brush border membrane vesicle by compounds according to the present invention;

FIG. 3 shows the inhibition of sodium-dependent phosphate uptake of Xenopus oocytes, which have expressed NaPi-2a by compounds according to the present invention; and

FIG. 4 shows the inhibition of sodium-dependent phosphate uptake of Xenopus oocytes, which have expressed NaPi-2a and NaPi-2b by compounds according to the present invention.

DETAILED DESCRIPTION OF THE INVENTION

Compounds

The terms “C_1-6 alkyl” and “C_1-6 alkoxy” as used herein as a group or a part of a group respectively mean straight chain or branched chain alkyl and alkoxy having 1 to 6 carbon atoms. Preferably, the “C_1-6 alkyl” and “C_1-6 alkoxy” may be C_1-4 alkyl and C_1-4 alkoxy, respectively.

The term “C_3-7 cycloalkyl” as used herein as a group or a part of a group means cyclic alkyl having 3 to 7 carbon atoms. Preferably, the “C_3-7 cycloalkyl” is C_5-7 cycloalkyl.

The terms “C_2-6 alkenyl” and “C_2-6 alkynyl” as used herein as a group or a part of a group respectively mean straight chain or branched chain alkenyl having 2 to 6 carbon atoms and alkynyl having 2 to 6 carbon atoms. Preferably, the “C_2-6 alkenyl” is C_2-4 alkenyl. Preferably, the “C_2-6 alkynyl” is C_2-4 alkynyl.

Examples of C_1-6 alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, i-butyl, s-butyl, t-butyl, n-pentyl, and n-hexyl.

Examples of C_1-6 alkoxy include methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, and t-butoxy.

Examples of C_3-7 cycloalkyl include cyclopropyl, cyclopentyl, and cyclohexyl.

Examples of C_2-6 alkenyl include allyl, butenyl, pentenyl, and hexenyl.

Examples of C_2-6 alkynyl include 2-propynyl, butynyl, pentynyl, and hexynyl.

The term “halogen atom” as used herein means a fluorine, chlorine, bromine, or iodine atom.

The terms “unsaturated carbocyclic ring” and “unsaturated heterocyclic ring” as used herein respectively mean carbocyclic ring and heterocyclic ring having one or more unsaturated bonds such as a double bond.

The term “aryl” as used herein means a monocyclic, bicyclic, or tricyclic aromatic hydrocarbon group. Examples of aryl include phenyl, naphthyl, and anthryl.

The term “aryl C_1-6 alkyl” as used herein means C_1-6 alkyl substituted by a monocyclic, bicyclic, or tricyclic aromatic hydrocarbon group. Examples of aryl C_1-6 alkyl include benzyl (C₆H₅CH₂—) and phenethyl (C₆H₅CH₂CH₂—).

Th term “arylamino” as used herein means amino substituted by a monocyclic, bicyclic, or tricyclic aromatic hydrocarbon group.

The term “aryl C_2-6 alkenyl” as used herein means C_2-6 alkenyl substituted by a monocyclic, bicyclic, or tricyclic aromatic hydrocarbon group. Examples of aryl C_2-6 alkenyl include phenylethenyl (C₆H₅—CH═CH—).

The term “heterocyclic group” as used herein means a saturated or unsaturated five- to nine-membered (preferably five- to seven-membered, more preferably five- or six-membered) monocyclic heterocyclic group and a saturated or unsaturated nine- to eleven-membered bicyclic heterocyclic group. The heterocyclic group contains one or more heteroatoms selected from oxygen, nitrogen, and sulfur atoms. Examples of the heterocyclic ring include pyridyl, furyl, thienyl, pyrrolyl, pyridazyl, pyrimidyl, pyrazyl, isoxazolyl, quinolyl, quinoxalinyl, and quinazolidyl.

In the di-C_1-6 alkylamino group as used herein, two C_1-6 alkyl groups attached to the nitrogen atom together may form “cyclic amino.” The term “cyclic amino” as used herein means a saturated five- to eight-membered heterocyclic group formed by combining two C_1-6 alkyl groups attached to the nitrogen atom with each other. The cyclic amino group may contain, in addition to the nitrogen atom in the amino group, 1 to 3 heteroatoms, preferably one oxygen atom, one nitrogen atom, or one sulfur atom. Examples of the saturated cyclic amino group include pyrrolidyl, piperidyl, piperazyl, morpholyl, thiomorpholyl, homopiperidyl, and [1,4]diazepine.

In the di-C_2-6 alkenylamino group as used herein, two C_2-6 alkenyl groups attached to the nitrogen atom together may form “unsaturated cyclic amino.” The term “cyclic amino” as used herein means an unsaturated five- to eight-membered heterocyclic group formed by combining two C_2-6 alkenyl groups attached to the nitrogen atom with each other. The cyclic amino group may contain, in addition to the nitrogen atom in the amino group, 1 to 3 heteroatoms, preferably one oxygen atom or one nitrogen atom. Examples of the unsaturated cyclic amino group include pyrrole, pyrazole, imidazolyl, and tetrahydropyridyl.

Compounds represented by formula (I) include hydrazine derivatives and quinazolone derivatives. When R¹⁰¹ and R¹⁰² together represent ═O and R¹⁰³ and R¹⁰⁴ represent a hydrogen atom, formula (I) represents hydrazine derivatives. When R¹⁰¹ and R¹⁰⁴ together represent a bond and when R¹⁰² and R¹⁰³ together represent a bond, formula (I) represent quinazolone derivatives.

In formula (I) and formula (I-1) and formula (I-2) which will be described later, the five- to nine-membered unsaturated carbocyclic moiety or five- to nine-membered unsaturated heterocyclic moiety represented by A may represent, for example, benzene ring moiety, cyclohexene ring moiety, or pyridine ring moiety.

In formula (I) and formula (I-1) and formula (I-2) which will be described later, when the carbocyclic moiety and hetrocyclic moiety represented by A are substituted by two substituents, (c) C_1-6 alkyl groups or (m) C_2-6 alkenyl groups, these alkyl groups or these alkenyl groups together may form a C_3-5 alkylene chain or a C_3-5 alkylene chain. In this case, A may represent, for example, naphthyl, quinolyl, benzo[b]thiophene, 4,5,6,7,-tetrahydrobenzo[b]thiophene, cyclopenta[b]thiophene, or quinazolyl.

In formula (I) and formulae (I-1) and (I-2) which will be described later, preferably, the five- to nine-membered unsaturated carbocyclic moiety or the five- to nine-membered unsaturated heterocyclic moiety represented by A may represent formula (IIa) or formula (IIa′): wherein R¹, R², R³, and R⁴, which may be the same or different, represent

(a) a halogen atom;

(b) hydroxyl;

(c) C_1-6 alkyl;

(d) C_1-6 alkoxy;

(e) aryl;

(f) aryloxy;

(g) arylthio;

(h) alkylthio;

(i) nitro;

(j) amino;

(i) nitro;

(j) amino;

(k) mono- or di-arylamino;

(l) mono- or di-C_1-6 alkylamino;

(m) C_2-6 alkenyl;

(n) C_2-6 alkenyloxy;

(o) C_2-6 alkenylthio;

(p) mono- or di-C_2-6 alkenylamino;

(q) carboxyl;

(r) C_1-6 alkyl- or aryl-oxycarbonyl; or

(s) a hydrogen atom,

(c) the C_1-6 alkyl group, (d) the C_1-6 alkoxy group, (e) the aryl group, (f) the aryloxy group, (g) the arylthio group, (h) the alkylthio group, (m) the C_2-6 alkenyl group, (n) the C_2-6 alkenyloxy group, and (o) the C_2-6 alkenylthio group are optionally substituted by (1) hydroxyl, (2) thiol, (3) amino, (4) C_1-6 alkoxy, (5) C_1-6 alkylthio, (6) C_1-6 alkylsulfonyl, (7) mono- or di-C_1-6 alkylamino in which the di-C_1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms, (8) aryloxy, (9) arylthio, (10) arylsulfonyl, (11) aryl, (12) a heterocyclic group, (13) a halogen atom, or (14) arylamino in which the amino group is optionally substituted by C_1-6 alkyl, and the aryl group is optionally substituted by halogen, C_1-6 alkyl, C_1-6 alkoxy, or C_1-6 alkylamino, (15) C_1-6 alkoxy-(CH₂CH₂O)m wherein m is an integer of 1 to 6, (16) carboxyl, (17) an oxygen atom (═O), or (18) C_3-7 cycloalkyl,

the aryl moiety in (k) the mono- or di-arylamino group is optionally substituted by (1) hydroxyl, (2) thiol, (3) amino, (4) C_1-6 alkoxy, (5) C_1-6 alkylthio, (6) C_1-6 alkylsulfonyl, (7) mono- or di-C_1-6 alkylamino in which the di-C_1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms, (8) aryloxy, (9) arylthio, (10) arylsulfonyl, (11) aryl, (12) a heterocyclic group, (13) a halogen atom, (14) arylamino in which the amino group is optionally substituted by C_1-6 alkyl, and the aryl group is optionally substituted by a halogen atom, C_1-6 alkyl, C_1-6 alkoxy, or C_1-6 alkylamino, (15) C_1-6 alkoxy-(CH₂CH₂O)m wherein m is an integer of 1 to 6, (16) carboxyl, (17) an oxygen atom (═O), or (18) C_3-7 cycloalkyl, and, in the case of the mono-arylamino group, the amino group is optionally substituted by C_1-6 alkyl optionally substituted by hydroxyl or a halogen atom,

in (l) the mono- or di-C_1-6 alkylamino, the di-C_1-6 alkyl group may form cyclic amino optionally containing 1 to 3 heteroatoms, and one or two alkyl groups on the amino group and the cyclic amino moiety are optionally substituted by a halogen atom; C_1-6 alkyl optionally substituted by hydroxyl, a halogen atom, or aryl optionally substituted by a halogen atom, C_1-6 alkyl, or C_1-6 alkyloxy, a heterocyclic group optionally substituted by a halogen atom, C_1-6 alkyl, or C_1-6 alkyloxy, and, when one or two alkyl groups on the amino group and the cyclic amino moiety are substituted by two C_1-6 alkyl groups, they together may form C_3-7 cycloalkyl; C_1-6 alkoxy; C_1-6 alkylthio; mono- or di-C_1-6 alkylamino in which the di-C_1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms, and one or two C_1-6 alkyl groups on the amino group and the cyclic amino moiety are optionally substituted by hydroxyl or a halogen atom; arylamino in which the amino group is optionally substituted by C_1-6 alkyl; mono- or di-C_1-6 alkylcarbamoylmethyl in which the di-C_1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms, and one or two alkyl groups on the amino group and the cyclic amino moiety are optionally substituted by hydroxyl; aryloxy; arylthio; an oxygen atom (═O); hydroxyl; carboxyl; C_1-6 alkoxy- or aryloxy-carbonyl; C_1-6 alkylcarbonyl; aryl optionally substituted by a halogen atom or hydroxyl; or a heterocyclic group,

in (p) the mono- or di-C_2-6 alkenylamino group, the amino group of the monoalkenylamino group is optionally substituted by C_1-6 alkyl optionally substituted by hydroxyl or a halogen atom, and the di-C_2-6 alkenyl together may form unsaturated cyclic amino optionally containing 1 to 3 heteroatoms, and one or two alkenyl groups on the amino group or the unsaturated cyclic amino moiety is optionally substituted by a halogen atom; C_1-6 alkyl optionally substituted by hydroxyl, a halogen atom, aryl optionally substituted by a halogen atom, C_1-6 alkyl, or C_1-6 alkyloxy, a heterocyclic group optionally substituted by a halogen atom, C_1-6 alkyl, or C_1-6 alkyloxy, and, when one or two alkyl groups on the amino group and the cyclic amino moiety are substituted by two C_1-6 alkyl groups, they together may form C_3-7 cycloalkyl; C_1-6 alkoxy; C_1-6 alkylthio; mono- or di-C_1-6 alkylamino in which the di-C_1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms, and one or two C_1-6 alkyl groups on the amino group and the cyclic amino moiety are optionally substituted by hydroxyl or a halogen atom; arylamino in which the amino group is optionally substituted by C_1-6 alkyl; mono- or di-C_1-6 alkylcarbamoylmethyl in which the di-C_1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms, and one or two alkyl groups on the amino group and the cyclic-amino moiety are optionally substituted by hydroxyl; aryloxy; arylthio; an oxygen atom (═O); hydroxyl; carboxyl; C_1-6 alkoxy- or aryloxy-carbonyl; C_1-6 alkylcarbonyl; aryl optionally substituted by a halogen atom or hydroxyl; or a heterocyclic group,

when the carbocyclic moiety and hetrocyclic moiety represented by A are substituted by two (c) C_1-6 alkyl groups or (m) C_2-6 alkenyl groups, preferably when positions of R² and R³ are substituted, the alkyl or alkenyl groups together with the carbon atoms to which they are respectively attached may form an unsaturated five- to seven-membered carbocyclic ring, and

* represents a bond to —C(═O)—N(-Z)(-R¹⁰⁴).

In formula (I) and formula (I-1) and formula (I-2) which will be described later, A may represent formula (IIa), and, in this case, preferably R¹, R², R³, and R⁴ represent

(a) a halogen atom;

(b) hydroxyl;

(c) C_1-6 alkyl;

(d) C_1-6 alkoxy;

(e) aryl;

(f) aryloxy;

(g) arylthio;

(h) alkylthio;

(i) nitro;

(j) amino; or

(k) a hydrogen atom, and

(c) the C_1-6 alkyl group, (d) the C_1-6 alkoxy group, (e) the aryl group, (f) the aryloxy group, (g) the arylthio group, and (h) the alkylthio group are optionally substituted by (1) hydroxyl, (2) thiol, (3) amino, (4) C_1-6 alkoxy, (5) C_1-6 alkylthio, (6) C_1-6 alkylsulfonyl, (7) mono- or di-C_1-6 alkylamino in which the di-C_1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms, (8) aryloxy, (9) arylthio, (10) arylsulfonyl, (11) aryl, (12) a heterocyclic group, (13) a halogen atom, or (14) arylamino in which the amino group is optionally substituted by C_1-6 alkyl, and the aryl group is optionally substituted by halogen, C_1-6 alkyl, C_1-6 alkoxy, or C_1-6 alkylamino.

In formula (I) and formula (I-1) and formula (I-2) which will be described later, when A represents formula (IIa) or formula (IIa′), preferably, R¹, R³, and R⁴, which may be the same or different, represent

a hydrogen atom;

a halogen atom;

C_1-6 alkyl in which the alkyl group is optionally substituted by C_1-6 alkoxy or a halogen atom;

aryl optionally substituted by C_1-6 alkoxy or a halogen atom;

C_1-6 alkoxy in which the alkoxy group is optionally substituted by C_1-6 alkoxy or a halogen atom; or

aryloxy optionally substituted by C_1-6 alkoxy or a halogen atom,

R² may represent

a hydrogen atom;

a halogen atom;

hydroxyl;

C_1-6 alkyl in which the alkyl group is optionally substituted by (1) hydroxyl, (2) thiol, (3) amino, (4) C_1-6 alkoxy, (5) C_1-6 alkylthio, (6) C_1-6 alkylsulfonyl, (7) mono- or di-C_1-6 alkylamino in which the di-C_1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms, (8) aryloxy, (9) arylthio, (10) arylsulfonyl, (11) aryl, (12) a heterocyclic group, (13) a halogen atom, or (14) arylamino in which the amino group is optionally substituted by C_1-6 alkyl, and the aryl group is optionally substituted by a halogen atom, C_1-6 alkyl, C_1-6 alkoxy, or C_1-6 alkylamino; or

C_1-6 alkoxy in which the alkoxy group is optionally substituted by (1) hydroxyl, (2) thiol, (3) amino, (4) C_1-6 alkoxy, (5) C_1-6 alkylthio, (6) C_1-6 alkylsulfonyl, (7) mono- or di-C_1-6 alkylamino in which di-C_1-6 alkylamino may form cyclic amino optionally containing 1 to 3 heteroatoms, (8) aryloxy, (9) arylthio, (10) arylsulfonyl, (11) aryl, (12) a heterocyclic group, or (13) a halogen atom,

more preferably,

R¹, R³, and R⁴ represent a hydrogen atom,

R² represents

a halogen atom;

hydroxyl;

C_1-6 alkyl optionally substituted by mono- or di-C_1-6 alkylamino; or

C_1-6 alkoxy optionally substituted by mono- or di-C_1-6 alkylamino.

In formula (I) and formula (I-1) and formula (I-2) which will be described later, when A represents formula (IIa) or formula (IIa′), preferably, R¹, R², R³, and R⁴, which may be the same or different, represent a hydrogen atom; a halogen atom; hydroxyl; optionally substituted C_1-6 alkyl; optionally substituted C_2-6 alkenyl; optionally substituted C_1-6 alkoxy; optionally substituted mono- or di-arylamino; optionally substituted mono- or di-C_1-6 alkylamino in which the dialkylamino together may form optionally substituted cyclic amino optionally containing 1 to 3 heteroatoms; optionally substituted mono- or di-C_2-6 alkenylamino in which the di-C_2-6 alkenylamino group together may form optionally substituted unsaturated cyclic amino optionally containing 1 to 3 heteroatoms, and, when R² and R³ are optionally substituted C_1-6 alkyl or optionally substituted C_2-6 alkenyl, the alkyl or alkenyl groups together with the carbon atoms to which R² and R³ are respectively attached may form an unsaturated five- to seven-membered carbocyclic ring, and, more preferably, R¹ and R⁴ represent a hydrogen atom.

In formula (I) and formula (I-1) and formula (I-2) which will be described later, when A represents formula (IIa) or formula (IIa′), preferably, R¹, R², R³, and R⁴, which may be the same or different, represent a hydrogen atom; a halogen atom; hydroxyl; optionally substituted C_1-6 alkyl; or optionally substituted C_1-6 alkoxy, and more preferably, R¹ and R⁴ represent a hydrogen atom.

In formula (I) and formula (I-1) and formula (I-2) which will be described later, when A represents formula (IIa) or formula (IIa′), R¹, R², R³, and R⁴ more preferably represent a hydrogen atom.

In formula (I) and formula (I-1) and formula (I-2) which will be described later, when A represents formula (IIa) or formula (IIa′), more preferably,

R¹ and R⁴ represent a hydrogen atom,

any one of R² and R³, preferably R², represents a halogen atom; hydroxyl; C_1-6 alkyl optionally having a substituent, preferably a halogen atom, mono- or di-alkylamino which may form cyclic amino, or hydroxyl; C_1-6 alkoxy optionally having a substituent, preferably a halogen atom, mono- or di-alkylamino which may form cyclic amino, hydroxyl, C_1-6 alkoxy-(CH₂CH₂O)m, wherein m is an integer of 1 to 6, or C_3-7 cycloalkyl; optionally substituted mono- or di-arylamino; mono- or di-C_1-6 alkylamino optionally having a substituent, preferably hydroxyl, C_1-6 alkyl optionally substituted by hydroxyl, an oxygen atom (═O), mono- or di-C_1-6 alkylamino which may form cyclic amino, or carboxyl, and the dialkylamino together may form cyclic amino optionally having a substituent, preferably hydroxyl, C_1-6 alkyl optionally substituted by hydroxyl, an oxygen atom (═O), mono- or di-C_1-6 alkylamino which may form cyclic amino, or carboxyl, and the cyclic amino group may contain 1 to 3 heteroatoms; optionally substituted mono- or di-C_2-6 alkenylamino, in which the di-C_2-6 alkenylamino group together may form optionally substituted unsaturated cyclic amino optionally containing 1 to 3 heteroatoms, and the other (preferably, R³) represents a hydrogen atom.

In the above preferred embodiment, more preferably, the cyclic amino group may be a five- to seven-membered heterocyclic group that optionally contains one oxygen atom, one nitrogen atom, or one sulfur atom in addition to the nitrogen atom in the amino group. Particularly preferred saturated cyclic amino groups include pyrrolidyl, piperidyl, piperazyl, morpholyl, thiomorpholyl, homopiperidyl, and [1,4]diazepine.

In formula (I) and formula (I-1) and formula (I-2) which will be described later, when A represents formula (IIa) or formula (IIa′), more preferably, R¹ and R⁴ represent a hydrogen atom, and any one of R² and R³ represents a halogen atom; hydroxyl; optionally substituted C_1-6 alkyl; optionally substituted C_1-6 alkoxy with the other representing a hydrogen atom.

In formula (I) and formula (I-1) and formula (I-2) which will be described later, when A represents formula (IIa) or formula (IIa′), more preferably, R¹ and R⁴ represent a hydrogen atom, and R² and R³, which may be the same or different, represent a halogen atom; hydroxyl; C_1-6 alkyl optionally having a substituent, preferably a halogen atom, mono- or di-alkylamino group which may form cyclic amino, or hydroxyl; C_1-6 alkoxy optionally having a substituent, preferably a halogen atom, mono- or di-alkylamino which may form cyclic amino, hydroxyl, C_1-6 alkoxy-(CH₂CH₂O)m wherein m is an integer of 1 to 6, or C_3-7 cycloalkyl.

In the above preferred embodiment, more preferably, the cyclic amino group may be a five- to seven-membered heterocyclic group that optionally contains one oxygen atom, one nitrogen atom, or one sulfur atom in addition to the nitrogen atom in the amino group. Particularly preferred saturated cyclic amino groups include pyrrolidyl, piperidyl, piperazyl, morpholyl, thiomorpholyl, homopiperidyl, and [1,4]diazepine.

In formula (I) and formula (I-1) and formula (I-2) which will be described later, when A represents formula (IIa) or formula (IIa′), more preferably, R¹ and R⁴ represent a hydrogen atom, and R² and R³ together with the carbon atoms to which they are respectively attached form an unsaturated five- to seven-membered carbocyclic ring. Particularly preferably, group A together with R² and R³ forms naphthyl or quinolyl.

In formula (I) and formula (I-1) and formula (I-2) which will be described later, when A represents formula (IIa) or formula (IIa′), more preferably, R¹ and R⁴ represent a hydrogen atom, and R² and R³, which may be the same or different, represent C_1-6 alkoxy optionally having a substituent (C_1-6 alkoxy-(CH₂CH₂O)m wherein m is an integer of 1 to 6).

In formula (I) and formula (I-1) and formula (I-2) which will be described later, when A represents formula (IIa) or formula (IIa′), more preferably, R¹ and R⁴ represent a hydrogen atom; any one of R² and R³ (preferably, R²) represents mono- or di-C_1-6 alkylamino optionally having a substituent, preferably hydroxyl, C_1-6 alkyl optionally substituted by hydroxyl, an oxygen atom (═O), mono- or di-C_1-6 alkylamino which may form cyclic amino, or carboxyl, and the dialkylamino group together may form cyclic amino optionally having a substituent, preferably hydroxyl, C_1-6 alkyl optionally substituted by hydroxyl, an oxygen atom (═O), mono- or di-C_1-6 alkylamino which may form cyclic amino, or carboxyl, and the cyclic amino group may contain 1 to 3 heteroatoms; and the other (preferably, R³) represents a hydrogen atom.

In the above preferred embodiment, more preferably, the cyclic amino group may be a five- to seven-membered heterocyclic group that optionally contains one oxygen atom, one nitrogen atom, or one sulfur atom in addition to the nitrogen atom in the amino group. Particularly preferred saturated cyclic amino groups include pyrrolidyl, piperidyl, piperazyl, morpholyl, thiomorpholyl, homopiperidyl, and [1,4]diazepine.

In formula (I) and formula (I-1) and formula (I-2) which will be described later, when A represents formula (IIa) or formula (IIa′), more preferably, R¹ and R⁴ represent a hydrogen atom; any one of R² and R³ (preferably, R²) represents C_1-6 alkoxy optionally having a substituent, preferably a halogen atom, mono- or di-alkylamino which may form cyclic amino, hydroxyl, C_1-6 alkoxy-(CH₂CH₂O)m wherein m is an integer of 1 to 6, or C_3-7 cycloalkyl; and the other (preferably, R³) represents a hydrogen atom.

In the above preferred embodiment, more preferably, the cyclic amino group may be a five- to seven-membered heterocyclic group that optionally contains one oxygen atom, one nitrogen atom, or one sulfur atom in addition to the nitrogen atom in the amino group. Particularly preferred saturated cyclic amino groups include pyrrolidyl, piperidyl, piperazyl, morpholyl, thiomorpholyl, homopiperidyl, and [1,4]diazepine.

In formula (I) and formula (I-1) and formula (I-2) which will be described later, preferably, the five- to nine-membered unsaturated carbocyclic moiety or the five- to nine-membered unsaturated heterocyclic moiety represented by A represents formula (IIb): wherein R³¹ and R³², which may be the same or different, represent a hydrogen atom; a halogen atom; or C_1-6 alkyl in which the alkyl group is optionally substituted by (1) hydroxyl, (2) thiol, (3) amino, (4) C_1-6 alkoxy, (5) C_1-6 alkylthio, (6) C_1-6 alkylsulfonyl, (7) mono- or di-C_1-6 alkylamino in which the di-C_1-6 alkylamino may form cyclic amino optionally containing 1 to 3 heteroatoms, (8) aryloxy, (9) arylthio, (10) arylsulfonyl, (11) aryl, (12) a heterocyclic group, (13) a halogen atom, or (14) arylamino in which the amino group is optionally substituted by C_1-6 alkyl, and the aryl group is optionally substituted by a halogen, C_1-6 alkyl, C_1-6 alkoxy, or C_1-6 alkylamino; or C_2-6 alkenyl,

when R³¹ and R³² represent alkyl or alkenyl, the alkyl or alkenyl groups together with the carbon atoms to which they are respectively attached may form an unsaturated five- to seven-membered carbocyclic ring, and

* represents a bond to —C(═O)—N(-Z)(-R¹⁰⁴).

In formula (I) and formula (I-1) and formula (I-2) which will be described later, when A represents formula (IIb), preferably,

R³¹ and R³², which may be the same or different, represent a hydrogen atom; a halogen atom; or C_1-6 alkyl in which the alkyl group is optionally substituted by (1) hydroxyl, (2) thiol, (3) amino, (4) C_1-6 alkoxy, (5) C_1-6 alkylthio, (6) C_1-6 alkylsulfonyl, (7) mono- or di-C_1-6 alkylamino in which the di-C_1-6 alkylamino may form cyclic amino optionally containing 1 to 3 heteroatoms, (8) aryloxy, (9) arylthio, (10) arylsulfonyl, (11) aryl, (12) a heterocyclic group, (13) a halogen atom, or (14) arylamino in which the amino group is optionally substituted by C_1-6 alkyl, and the aryl group is optionally substituted by a halogen, C_1-6 alkyl, C_1-6 alkoxy, or C_1-6 alkylamino,

when R³¹ and R³² represent alkyl, the alkyl groups together with the carbon atoms to which they are respectively attached may form an unsaturated five- to seven-membered carbocyclic ring, and, in this case, R³¹ and R³² together form a C_3-5 alkylene chain, and represents a double bond.

In formula (I) and formula (I-1) and formula (I-2) which will be described later, when A represents formula (IIb), more preferably,

(i) R³¹ and R³² represent a hydrogen atom, or

(ii) any one of R³¹ and R³² represents a hydrogen atom, and the other represents C_1-6 alkyl optionally substituted by mono- or di-C_1-6 alkylamino, which may form cyclic amino, preferably piperidyl, morpholyl, and thiomorpholyl, or by a halogen atom, and the cyclic amino group may contain 1 to 3 heteroatoms, or

(iii) R³¹ and R³², which may be the same or different, represent C_1-6 alkyl optionally substituted by mono- or di-C_1-6 alkylamino, which may form cyclic amino, preferably piperidyl, morpholyl, and thiomorpholyl, or by a halogen atom, and the cyclic amino group may contain 1 to 3 heteroatoms, or

(iv) R³¹ and R³² together with the carbon atoms to which they are respectively attached form a saturated or unsaturated five- to seven-membered carbocyclic ring, preferably a cyclohexane ring, a benzene ring, and a cyclopentane ring.

In formula (I) and formula (I-1) and formula (I-2) which will be described later, when A represents formula (IIb), more preferably, R³¹ and R³² represent a hydrogen atom, or any one of R³¹ and R³² represents a hydrogen atom with the other representing C_1-6 alkyl optionally substituted by a halogen atom, or R³¹ and R³² together with the carbon atoms to which they are respectively attached form an unsaturated five- to seven-membered carbocyclic ring. In this case, R³¹ and R³² together may form a C_3-5 alkylene chain, and may represent a double bond.

In formula (I) and formula (I-1) and formula (I-2) which will be described later, preferably, the five- to nine-membered unsaturated carbocyclic moiety or the five- to nine-membered unsaturated heterocyclic moiety represented by A represents formula (IIc):

wherein R³³ and R³⁴, which may be the same or different, represent a hydrogen atom; a halogen atom; or C_1-6 alkyl in which the alkyl group is optionally substituted by (1) hydroxyl, (2) thiol, (3) amino, (4) C_1-6 alkoxy, (5) C_1-6 alkylthio, (6) C_1-6 alkylsulfonyl, (7) mono- or di-C_1-6 alkylamino in which the di-C_1-6 alkylamino may form cyclic amino optionally containing 1 to 3 heteroatoms, (8) aryloxy, (9) arylthio, (10) arylsulfonyl, (11) aryl, (12) a heterocyclic group, (13) a halogen atom, or (14) arylamino in which the amino group is optionally substituted by C_1-6 alkyl, and the aryl group is optionally substituted by a halogen, C_1-6 alkyl, C_1-6 alkoxy, or C_1-6 alkylamino,

when R³³ and R³⁴ represent alkyl, the alkyl groups together with the carbon atoms to which they are respectively attached may form an unsaturated five- to seven-membered carbocyclic ring, and

* represents a bond to —C(═O)—N(-Z)(-R¹⁰⁴).

In formula (I) and formula (I-1) and formula (I-2) which will be described later, when A represents formula (IIc), preferably,

R³³ and R³⁴, which may be the same or different, represent a hydrogen atom; a halogen atom; or C_1-6 alkyl in which the alkyl group is optionally substituted by (1) hydroxyl, (2) thiol, (3) amino, (4) C_1-6 alkoxy, (5) C_1-6 alkylthio, (6) C_1-6 alkylsulfonyl, (7) mono- or di-C_1-6 alkylamino in which the di-C_1-6 alkylamino may form cyclic amino optionally containing 1 to 3 heteroatoms, (8) aryloxy, (9) arylthio, (10) arylsulfonyl, (11) aryl, (12) a heterocyclic group, (13) a halogen atom, or (14) arylamino in which the amino group is optionally substituted by C_1-6 alkyl, and the aryl group is optionally substituted by a halogen, C_1-6 alkyl, C_1-6 alkoxy, or C_1-6 alkylamino,

when R³³ and R³⁴ represent alkyl, the alkyl groups together with the carbon atoms to which they are respectively attached may form an unsaturated five- to seven-membered carbocyclic ring, and, in this case, R³³ and R³⁴ together form a C_3-5 alkylene chain, and represents a double bond.

In formula (I) and formula (I-1) and formula (I-2) which will be described later, when A represents formula (IIc), more preferably,

(i) R³³ and R³⁴ represent a hydrogen atom, or

(ii) any one of R³³ and R³⁴ represents a hydrogen atom, and the other represents C_1-6 alkyl optionally substituted by mono- or di-C_1-6 alkylamino, which may form cyclic amino, preferably piperidyl, morpholyl, and thiomorpholyl, or by a halogen atom, and the cyclic amino group may contain 1 to 3 heteroatoms, or

(iii) R³³ and R³⁴, which may be the same or different, represent C_1-6 alkyl optionally substituted by mono- or di-C_1-6 alkylamino, which may form cyclic amino, preferably piperidyl, morpholyl, and thiomorpholyl, or by a halogen atom, and the cyclic amino group may contain 1 to 3 heteroatoms, or

(iv) R³³ and R³⁴ together with the carbon atoms to which they are respectively attached form a saturated or unsaturated five- to seven-membered carbocyclic ring, preferably a cyclohexane ring, a benzene ring, and a cyclopentane ring.

In formula (I) and formula (I-1) and formula (I-2) which will be described later, when A represents formula (IIc), more preferably, R³³ and R³⁴ represent a hydrogen atom, or any one of R³³ and R³⁴ represents a hydrogen atom with the other representing C_1-6 alkyl optionally substituted by a halogen atom, or R³³ and R³⁴ together with the carbon atoms to which they are respectively attached form an unsaturated five- to seven-membered carbocyclic ring. In this case, R³³ and R³⁴ together may form a C_3-5 alkylene chain, and may represent a double bond.

In formula (I) and formula (I-1) and formula (I-2) which will be described later, preferably, the five- to nine-membered saturated or unsaturated carbocyclic moiety or the five- to nine-membered saturated or unsaturated heterocyclic moiety represented by A represents formula (IId): wherein R³⁵ and R³⁶, which may be the same or different, represent a hydrogen atom; a halogen atom; or C_1-6 alkyl in which the alkyl group is optionally substituted by (1) hydroxyl, (2) thiol, (3) amino, (4) C_1-6 alkoxy, (5) C_1-6 alkylthio, (6) C_1-6 alkylsulfonyl, (7) mono- or di-C_1-6 alkylamino in which the di-C_1-6 alkylamino may form cyclic amino optionally containing 1 to 3 heteroatoms, (8) aryloxy, (9) arylthio, (10) arylsulfonyl, (11) aryl, (12) a heterocyclic group, (13) a halogen atom, or (14) arylamino in which the amino group is optionally substituted by C_1-6 alkyl, and the aryl group is optionally substituted by a halogen, C_1-6 alkyl, C_1-6 alkoxy, or C_1-6 alkylamino; or C_2-6 alkenyl, and

* represents a bond to —C(═O)—N(-Z)(-R¹⁰⁴).

In formula (I) and formula (I-1) and formula (I-2) which will be described later, when A represents formula (IId), more preferably, R³⁵ and R³⁶ represent a hydrogen atom, or any one of R³⁵ and R³⁶ represents a hydrogen atom with the other representing C_1-6 alkyl optionally substituted by a halogen atom.

In formula (I) and formula (I-1) and formula (I-2) which will be described later, preferably, R⁵ may represent optionally substituted C_5-7 cycloalkyl, optionally substituted aryl, more preferably phenyl or naphthyl, an optionally substituted saturated or unsaturated five- or six-membered heterocyclic group, more preferably pyridyl, furyl, thienyl, isoxazole, and pyrimidyl, or an optionally substituted saturated or unsaturated nine- to eleven-membered bicyclic heterocyclic group, more preferably quinoxalinyl.

In formula (I) and formula (I-1) and formula (I-2) which will be described later, particularly preferably, R⁵ represents a cyclic group selected from C_5-7 cycloalkyl, phenyl, pyridyl, furyl, thienyl, isoxazole, pyrimidyl, and quinoxalinyl, in which the cyclic group is optionally substituted by a halogen atom; C_1-6 alkyl optionally substituted by a halogen atom; C_1-6 alkoxy optionally substituted by a halogen atom; or hydroxyl.

In formula (I) and formula (I-1) and formula (I-2) which will be described later, paricularly preferably, R⁵ represents a cyclic group selected from C_5-7 cycloalkyl, phenyl, pyridyl, furyl, thienyl, isoxazole, pyrimidyl, and quinoxalinyl, in which the cyclic group is optionally substituted by C_1-6 alkyl in which the alkyl group is optionally substituted by optionally substituted C_1-6 alkoxy, optionally substituted C_1-6 alkylthio, optionally substituted C_1-6 alkylsulfinyl, optionally substituted C_1-6 alkylsulfonyl, or optionally substituted mono- or di-C_1-6 alkylamino in which the di-C_1-6 alkylamino may form cyclic amino optionally containing 1 to 3 heteroatoms.

In formula (I) and formula (I-1) and formula (I-2) which will be described later, preferably, R⁵ represents a group of formula (IIIa), (IIIb), or (IIIc): wherein

D, E, J, L, and M, which may be the same or different, represent a carbon or nitrogen atom,

G represents an oxygen or sulfur atom,

R⁸, R⁹, R¹⁰, R¹¹, and R¹², which may be the same or different, represent

(I) a halogen atom;

(II) C_1-6 alkyl optionally containing a substituent selected from the group consisting of (1) hydroxyl, (2) thiol, (3) amino, (4) C_1-6 alkoxy, (5) C_1-6 alkylthio, (6) C_1-6 alkylsulfinyl, (7) C_1-6 alkylsulfonyl, (8) mono- or di-C_1-6 alkylamino, (8′) amino substituted by a heterocyclic group optionally substituted by C_1-6 alkyl, (9) C_1-6 alkylcarbonyloxy, (10) C_1-6 alkylcarbonylthio, (11) C_1-6 alkylcarbonylamino, (12) aryloxy, (13) arylthio, (14) arylsulfinyl, (15) arylsulfonyl, (16) arylamino, (17) C_1-6 alkyl- or aryl-sulfonylamino, (18) C_1-6 alkyl- or aryl-ureido, (19) C_1-6 alkoxy- or aryloxy-carbonylamino, (20) C_1-6 alkylamino- or arylamino-carbonyloxy, (21) carboxyl, (22) nitro, (23) a heterocyclic group, (23′) Het-S(═O)j- wherein Het represents a heterocyclic group, j is 0, 1, or 2, and Het is optionally substituted by alkyl optionally substituted by mono- or di-C_1-6 alkylamino in which the di-C_1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms and one or two alkyl groups on the amino group and the cyclic amino moiety are optionally substituted by hydroxyl, (24) cyano, and (25) a halogen atom,

wherein the alkyl moiety in (4) the C_1-6 alkoxy group, (5) the C_1-6 alkylthio group, (6) the C_1-6 alkylsulfinyl group, and (7) the C_1-6 alkylsulfonyl group is optionally substituted by a hydrogen atom, a halogen atom; C_1-6 alkyl; C_1-6 alkoxy; C_1-6 alkylthio; mono- or di-C_1-6 alkylamino in which the di-C_1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms; aryloxy; arylthio; hydroxyl; carboxyl; —S(═O)₂(—OH); C_1-6 alkoxy- or aryloxy-carbonyl; C_1-6 alkylcarbonyl; aryl; or a heterocyclic group optionally substituted by alkyl optionally substituted by mono- or di-C_1-6 alkylamino in which the di-C_1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms, and one or two alkyl groups on the amino group and the cyclic amino moiety are optionally substituted by hydroxy, and

in (8) the mono- or di-C_1-6 alkylamino group, the di-C_1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms, and one or two alkyl groups on the amino group and the cyclic amino moiety are optionally substituted by a halogen atom; C_1-6 alkyl optionally substituted by hydroxyl, a halogen atom, aryl optionally substituted by a halogen atom, C_1-6 alkyl, or C_1-6 alkyloxy, or a heterocyclic group optionally substituted by a halogen atom, C_1-6 alkyl, or C_1-6 alkyloxy, and, when one or two alkyl groups on the amino group and the cyclic amino moiety are substituted by two C_1-6 alkyl groups, they together may form C_3-7 cycloalkyl; C_1-6 alkoxy; C_1-6 alkylthio; mono- or di-C_1-6 alkylamino in which the di-C_1-6 alkylamino may form cyclic amino optionally containing 1 to 3 heteroatoms, and one or two alkyl groups on the amino group and the cyclic amino moiety are optionally substituted by hydroxyl; arylamino in which the amino group is optionally substituted by C_1-6 alkyl; mono- or di-C_1-6 alkylcarbamoylmethyl in which the di-C_1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms, and one or two alkyl groups on the amino group and the cyclic amino moiety are optionally substituted by hydroxyl; aryloxy; arylthio; an oxygen atom (═O); hydroxyl; carboxyl; C_1-6 alkoxy- or aryloxy-carbonyl; C_1-6 alkylcarbonyl; aryl optionally substituted by a halogen atom or hydroxyl; or a heterocyclic group, preferably a five- to seven-membered saturated or unsaturated heterocyclic group, more preferably pyridyl, pyrimidyl, and pyridazyl, and, when one carbon atom in the cyclic amino moiety is substituted by two C_1-6 alkoxy groups which may be the same or different, the two alkoxy groups together may form group —O—(CH₂)p-O— wherein p is an integer of 2 to 4, and the cyclic amino group may condense with a monocyclic or bicyclic aromatic carbocyclic ring, preferably phenyl or naphthyl, or a monocyclic or bicyclic aromatic heterocyclic ring, preferably pyridyl or naphthyridyl, to represent a bicyclic or tricyclic heterocyclic group;

(III) C_1-6 alkoxy optionally substituted by a halogen atom;

(IV) C_1-6 alkylthio optionally substituted by a halogen atom;

(V) C_3-7 cycloalkyl;

(VI) aryl;

(VII) aryloxy;

(VIII) C_1-6 alkylcarbonylamino;

(VIX) C_1-6 alkylcarbonyloxy;

(X) hydroxyl;

(XI) nitro;

(XII) cyano;

(XIII) amino;

(XIV) mono- or di-C_1-6 alkylamino in which the di-C_1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms;

(XV) arylamino;

(XVI) C_1-6 alkyl- or aryl-sulfonylamino;

(XVII) C_1-6 alkyl- or aryl-ureido;

(XVIII) C_1-6 alkoxy- or aryloxy-carbonylamino;

(XIX) C_1-6 alkylamino- or arylamino-carbonyloxy;

(XX) C_1-6 alkoxy- or aryloxy-carbonyl;

(XXI) acyl;

(XXII) carboxyl;

(XXIII) carbamoyl;

(XXIV) mono- or di-alkylcarbamoyl;

(XXV) a heterocyclic group;

(XXVI) alkyl- or aryl-sulfonyl;

(XXVII) C_2-6 alkenyloxy;

(XXVIII) C_2-6 alkynyloxy; or

(XXIX) a hydrogen atom, and

when D, E, J, L, or M represents a nitrogen atom, R⁸, R⁹, R¹⁰, R¹¹, and R¹² each are absent, or otherwise together with a nitrogen atom may form N-oxide (N→O).

In formula (I) and formula (I-1) and formula (I-2) which will be described later, when R⁵ represents formula (IIIa), formula (IIIb) and formula (IIIc), preferably, R⁸, R⁹, R¹⁰, R¹¹, and R¹², which may be the same or different, represent

a hydrogen atom;

a halogen atom;

hydroxymethyl; or

C_1-6 alkyl optionally substituted by a halogen atom.

In formula (I) and formula (I-1) and formula (I-2) which will be described later, when R⁵ represents formula (IIIa), formula (IIIb) and formula (IIIc), preferably, the substituted C_1-6 alkyl which may be represented by R⁸, R⁹, R¹⁰, R¹¹, and R¹² represents a group of formula (IV): —CH₂-Q-X1-R¹³  (IV) wherein

Q represents an oxygen atom, a sulfur atom, sulfinyl, or sulfonyl,

X1 represents a bond or straight chain or branched chain alkylene having 1 to 5 carbon atoms,

R¹³ represents a hydrogen atom, a halogen atom, C_1-6 alkyl, C_1-6 alkoxy, C_1-6 alkylthio, mono- or di-C_1-6 alkylamino in which the di-C_1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms, aryloxy, arylthio, hydroxyl, carboxyl, —S(═O)₂(—OH), C_1-6 alkoxy- or aryloxy-carbonyl, C_1-6 alkylcarbonyl, aryl, or a heterocyclic group optionally substituted by C_1-6 alkyl optionally substituted by mono- or di-C_1-6 alkylamino in which the di-C_1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms, and one or two alkyl groups on the amino group and the cyclic amino moiety are optionally substituted by hydroxyl, and this heterocyclic group preferably represents a five- or six-membered saturated or unsaturated heterocyclic group; or a group of formula (V) wherein

X2 represents a bond or straight chain or branched chain alkylene having 1 to 5 carbon atoms,

X3 represents a bond or straight chain or branched chain alkylene having 1 to 5 carbon atoms,

R¹⁴ and R¹⁵, which may be the same or different, represent a hydrogen atom; a halogen atom; C_1-6 alkyl optionally substituted by hydroxyl, a halogen atom, aryl optionally substituted by a halogen atom, C_1-6 alkyl, or C_1-6 alkyloxy, a heterocyclic group optionally substituted by a halogen atom, C_1-6 alkyl, or C_1-6 alkyloxy, and, when one or two alkyl groups on the amino group and the cyclic amino moiety are substituted by two C_1-6 alkyl groups, they together may form C_3-7 cycloalkyl; C_1-6 alkoxy; C_1-6 alkylthio; mono- or di-C_1-6 alkylamino in which the di-C_1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms, and one or two alkyl groups on the amino group and the cyclic amino moiety are optionally substituted by hydroxyl; arylamino in which the amino group is optionally substituted by C_1-6 alkyl; mono- or di-C_1-6 alkylcarbamoylmethyl in which the di-C_1-6 alkylamino may form cyclic amino optionally containing 1 to 3 heteroatoms, and one or two alkyl groups on the amino group and the cyclic amino moiety are optionally substituted by hydroxyl; aryloxy; arylthio; an oxygen atom (═O); hydroxyl; carboxyl; C_1-6 alkoxy- or aryloxy-carbonyl; C_1-6 alkylcarbonyl; aryl optionally substituted by a halogen atom or hydroxyl; or a heterocyclic group, preferably a five- or six-membered saturated or unsaturated heterocyclic group, provided that, when X2 represents a bond, R¹⁴ represents a hydrogen atom, or when X3 represents a bond, R¹⁵ represents a hydrogen atom, or

R¹⁴ and R¹⁵ together with a nitrogen atom to which they are respectively attached may form a heterocyclic group that may contain 1 to 3 heteroatoms, preferably one oxygen atom, one nitrogen atom, or one sulfur atom, in addition to the nitrogen atom, to which R¹⁴ and R¹⁵ are attached, and is optionally substituted by hydroxyl; C_1-6 alkyl optionally substituted by hydroxyl, a halogen atom, aryl optionally substituted by a halogen atom, C_1-6 alkyl, or C_1-6 alkyloxy, or a heterocyclic group optionally substituted by a halogen atom, C_1-6 alkyl, or C_1-6 alkyloxy, and, when one or two alkyl groups on the amino group and the cyclic amino moiety are substituted by two C_1-6 alkyl groups, they together may form C_3-7 cycloalkyl; mono- or di-C_1-6 alkylamino in which the di-C_1-6 alkylamino may form cyclic amino optionally containing 1 to 3 heteroatoms, and one or two alkyl groups on the amino group and the cyclic amino moiety are optionally substituted by hydroxyl; a saturated or unsaturated five- or six-membered heterocyclic group; mono- or di-C_1-6 alkylcarbamoylmethyl in which the di-C_1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms, and one or two alkyl groups on the amino group and the cyclic amino moiety are optionally substituted by hydroxyl; phenyl; or an oxygen atom (═O), and, when one carbon atom in the cyclic amino moiety is substituted by two —C_1-6 alkoxy groups which may be the same or different, the two alkoxy groups together may form group —O—(CH₂)p-O— wherein p is an integer of 2 to 4, and the cyclic amino group may condense with a monocyclic or bicyclic aromatic carbocyclic ring, preferably phenyl or naphthyl, or a monocyclic or bicyclic aromatic heterocyclic ring, preferably pyridyl or naphthyridyl, to represent a bicyclic or tricyclic heterocyclic group.

Preferably, the cyclic amino group present in formula (IV) and formula (V) may be a five- to seven-membered heterocyclic group that optionally contains one oxygen atom, one nitrogen atom, or one sulfur atom in addition to the nitrogen atom in the amino group, more preferably piperidyl, piperazyl, morpholyl, and thiomorpholyl.

In formula (I) and formula (I-1) and formula (I-2) which will be described later, when R⁵ represents formula (IIa), formula (IIIb) or formula (IIIc), preferably, D, E, J, L, and M represent a carbon atom.

In formula (I) and formula (I-1) and formula (I-2) which will be described later, when R⁵ represents formula (IIIa), formula (IIIb) or formula (IIIc), preferably, any one or two of D, E, J, L, and M represent a nitrogen atom and the others represent a carbon atom.

In formula (I) and formula (I-1) and formula (I-2) which will be described later, when R⁵ represents formula (IIIa), preferably, D, E, J, L, and M represent a carbon atom.

In formula (I) and formula (I-1) and formula (I-2) which will be described later, when R⁵ represents formula (IIIa), preferably, any one or two of D, E, J, L, and M represent a nitrogen atom with the others representing a carbon atom.

In formula (I) and formula (I-1) and formula (I-2) which will be described later, when R⁵ represents formula (IIIb), preferably, D, E, and J represent a carbon atom, and G represents an oxygen or sulfur atom.

In formula (I) and formula (I-1) and formula (I-2) which will be described later, when R⁵ represents formula (IIIc), preferably, D, E, and J represent a carbon atom, and G represents an oxygen or sulfur atom.

In formula (I) and formula (I-1) and formula (I-2) which will be described later, when R⁵ represents formula (IIIa), preferably, D, E, J, L, and M represent a carbon atom, any one of R⁸, R⁹, R¹⁰, R¹¹, and R¹² represents a group other than a hydrogen atom, and the others represent a hydrogen atom.

In formula (I) and formula (I-1) and formula (I-2) which will be described later, when R⁵ represents formula (IIIa), preferably, D, E, J, L, and M represent a carbon atom, any one of R⁸, R⁹, R¹⁰, R¹¹, and R¹² represents a halogen atom; optionally substituted C_1-6 alkyl; or optionally substituted C_1-6 alkoxy, and the other groups represent a hydrogen atom.

In formula (I) and formula (I-1) and formula (I-2) which will be described later, when R⁵ represents formula (IIIa), preferably, D, E, J, L, and M represent a carbon atom, R¹⁰ represents a group other othan a hydrogen atom, preferably substituted C_1-6 alkyl, more preferably a group of formula (IV) or formula (V), and R⁸, R⁹, R¹¹, and R¹² represent a hydrogen atom.

In formula (I) and formula (I-1) and formula (I-2) which will be described later, when R⁵ represents formula (IIIa), preferably, D, E, J, L, and M represent a carbon atom, R¹¹ represents a group other than a hydrogen atom, preferably substituted C_1-6 alkyl, more preferably a group of formula (IV) or formula (V), and R⁸, R⁹, R¹⁰, and R¹² represent a hydrogen atom.

In formula (I) and formula (I-1) and formula (I-2) which will be described later, when R⁵ represents formula (IIIa), preferably, D, E, J, L, and M represent a carbon atom, and any two of R⁸, R⁹, R¹⁰, R¹¹, and R¹² represent a group other than a hydrogen atom with the others representing a hydrogen atom.

In formula (I) and formula (I-1) and formula (I-2) which will be described later, when R⁵ represents formula (IIIa), preferably, D, E, J, L, and M represent a carbon atom, R¹⁰ and R¹¹ represent a group other than a hydrogen atom, preferably optionally substituted C_1-6 alkoxy, more preferably optionally substituted methoxy, and R⁸, R⁹, and R¹² represent a hydrogen atom.

In formula (I) and formula (I-1) and formula (I-2) which will be described later, when R⁵ represents formula (IIIa), preferably, D, E, J, L, and M represent a carbon atom, R⁹ and Rat represent a group other than a hydrogen atom, preferably, optionally substituted C_1-6 alkoxy, more preferably optionally substituted methoxy, and R⁸, R¹⁰, and R¹² represent a hydrogen atom.

In formula (I) and formula (I-1) and formula (I-2) which will be described later, when R⁵ represents formula (IIIb) and formula (IIIc), preferably, D, E, and J represent a carbon atom.

In formula (I) and formula (I-1) and formula (I-2) which will be described later, when R⁵ represents formula (IIIb) and formula (IIIc), preferably, any one or two of D, E, and J represent a nitrogen atom with the other(s) representing a carbon atom.

In formula (I) and formula (I-1) and formula (I-2) which will be described later, when R⁵ represents formula (IIIa), preferably,

D, E, J, L, and M represent a carbon atom,

any one or two of R⁸, R⁹, R¹⁰, R¹¹, and R¹², which may be the same or different, represent a halogen atom; hydroxymethyl; C_1-6 alkyl optionally substituted by a halogen atom; or C_1-6 alkoxy optionally substituted by a halogen atom, and the others represent a hydrogen atom.

In formula (I) and formula (I-1) and formula (I-2) which will be described later, when R⁵ represents formula (IIIa), preferably,

any one or two of D, E, J, L, and M represent a nitrogen atom, and the others represent a carbon atom,

any one or two of R⁸, R⁹, R¹⁰, R¹¹, and R¹², which may be the same or different, represent a halogen atom; hydroxymethyl; C_1-6 alkyl optionally substituted by a halogen atom, or C_1-6 alkoxy optionally substituted by a halogen atom, and the others reperesent a hydrogen atom.

In formula (I) and formula (I-1) and formula (I-2) which will be described later, when R⁵ represents formula (IIIb), preferably,

D, E, and J represent a carbon atom, and G represents an oxygen or sulfur atom,

one or two of R⁸, R⁹, and R¹⁰, which may be the same or different, represent a halogen atom; hydroxymethy; C_1-6 alkyl optionally substituted by a halogen atom; or C_1-6 alkoxy optionally substituted by a halogen atom, and the others represent a hydrogen atom.

In formula (I) and formula (I-1) and formula (I-2) which will be described later, when R⁵ represents formula (IIIc), preferably,

D, E, and J represent a carbon atom, and G represents an oxygen or sulfur atom,

one or two of R⁸, R⁹, and R¹⁰, which may be the same or different, represent a halogen atom; hydroxymethyl; C_1-6 alkyl optionally substituted by a halogen atom; or C_1-6 alkoxy optionally substituted by a halogen atom, and the others represent a hydrogen atom.

In formula (I) and formula (I-1) and formula (I-2) which will be described later, when R⁵ represents formula (IIIa), preferably,

D, E, J, L, and M represent a carbon atom,

R⁸, R⁹, and R¹² represent a hydrogen atom,

one of R¹⁰ and R¹¹ represents a group of formula (IV) wherein Q, X1, and R¹³ are as defined above, or a group of formula (V) wherein X2, X3, R¹⁴, and R¹⁵ are as defined above with the other groups representing a hydrogen atom.

In formula (I) and formula (I-1) and formula (I-2) which will be described later, when R⁵ represents formula (IIIa), preferably,

any one or two of D, E, J, L, and M represent a nitrogen atom, and the others represent a carbon atom,

R⁸, R⁹, and R¹² represent a hydrogen atom,

one of R¹⁰ and R¹¹ represents a group of formula (IV) wherein Q, X1, and R¹³ are as defined above, or a group of formula (V) wherein X2, X3, R¹⁴, and R¹⁵ are as defined above with the other groups representing a hydrogen atom.

In formula (I) and formula (I-1) and formula (I-2) which will be described later, when R⁵ represents formula (IIIb), preferably,

D, E, and J represent a carbon atom, and G represents an oxygen or sulfur atom,

one of R⁸, R⁹, and R¹⁰ represents a group of formula (IV) wherein Q, X1, and R¹³ are as defined above, or a group of formula (V) wherein X2, X3, R¹⁴, and R¹⁵ are as defined above with the others representing a hydrogen atom.

In formula (I) and formula (I-1) and formula (I-2) which will be described later, when R⁵ represents formula (IIIc), preferably,

D, E, and J represent a carbon atom, and G represents an oxygen or sulfur atom,

one of R⁸, R⁹, and R¹⁰ represents a group of formula (IV) wherein Q, X1, and R¹³ are as defined above, or a group of formula (V) wherein X2, X3, R¹⁴, and R¹⁵ are as defined above with the others representing a hydrogen atom.

In formula (I) and formula (I-1) and formula (I-2) which will be described later, preferably, R⁶ represents a hydrogen atom; optionally substituted C_1-6 alkyl; or optionally substituted aryl.

In formula (I) and formula (I-1) and formula (I-2) which will be described later, more preferably, R⁶ represents a hydrogen atom; C_1-6 alkyl optionally substituted by a halogen atom or C_1-6 alkoxy; or aryl optionally substituted by a halogen atom, C_1-6 alkyl, or C_1-6 alkoxy, most preferably, a hydrogen atom, or C_1-6 alkyl.

In formula (I) and formula (I-1) and formula (I-2) which will be described later, preferably, R⁷ represents optionally substituted aryl, optionally substituted aryl C_1-6 alkyl, optionally substituted aryl C_2-6 alkenyl, or optionally substituted saturated or unsaturated five- or six-membered heterocyclic group.

In formula (I) and formula (I-1) and formula (I-2) which will be described later, more preferably, R⁷ represents a cyclic group selected from phenyl, naphthyl, furyl, pyrrolyl, and thienyl, and the cyclic group is optionally substituted by a halogen atom; C_1-6 alkyl optionally substituted by a halogen atom; C_1-6 alkoxy in which the alkoxy group is optioinally substituted by a halogen atom, aryloxy optionally substituted by a halogen atom and C_1-6 alkyl, C_1-6 alkoxy in which the alkoxy group is optionally substituted by mono- or di-C_1-6 alkylamine in which the di-C_1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms, or a halogen atom, arylthio optionally substituted by a halogen atom and C_1-6 alkyl, C_1-6 alkylthio in which the alkylthio group is optionally substituted by mono- or di-C_1-6 alkylamine in which the di-C_1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms, or a halogen atom, arylamino optionally substituted by C_1-6 alkyl, mono- or di-C_1-6 alkylamine in which the di-C_1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms; hydroxyl; mono- or di-C_1-6 alkylamino in which the di-C_1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms; nitro; C_2-6 alkenyloxy; or C_2-6 alkynyloxy.

In formula (I) and formula (I-1) and formula (I-2) which will be described later, preferably, R⁶ represents a hydrogen atom or C_1-6 alkyl, R⁷ represents optionally substituted aryl, preferably phenyl or naphthyl, optionally substituted aryl, preferably phenyl or naphthyl, C_1-6 alkyl, optionally substituted aryl, preferably phenyl or naphthyl, C_2-6 alkenyl, or optionally substituted saturated or unsaturated five- or six-membered heterocyclic group, preferably furyl, thienyl, pyrrolyl, or pyridyl.

Among the compounds of formula (I), hydrazine derivatives may be represented by formula (I-1). wherein A, R⁵, Z, and are as defined in formula (I).

In formula (I-1), preferably,

A represents formula (IIa) or formula (IIa′) wherein R¹, R², R³, and R⁴ are as defined in formula (IIa) and formula (IIa′) and are preferably the same or different and represent a hydrogen atom; a halogen atom; hydroxyl; optionally substituted C_1-6 alkyl; or optionally substituted C_1-6 alkoxy,

R⁵ represents optionally substituted C_5-7 cycloalkyl, optionally substituted aryl, preferably phenyl, or optionally substituted saturated or unsaturated five- or six-membered heterocyclic group, preferably pyridyl, thienyl, isoxazole, or pyrimidyl and more preferably represents a group of formula (IIIa), formula (IIIb) or formula (IIIc), and

Z represents group (A), group (B), or group (C) wherein R⁶ represents a hydrogen atom or C_1-6 alkyl, R⁷ represents optionally substituted aryl, preferably phenyl or naphthyl, optionally substituted aryl, preferably phenyl or naphthyl, C_1-6 alkyl, optionally substituted aryl, preferably phenyl or naphthyl, C_2-6 alkenyl, or optionally substituted saturated or unsaturated five- or six-membered heterocyclic group, preferably furyl, thienyl, pyrrolyl, or pyridyl, and R¹⁷ represents a hydrogen atom.

In formula (I-1), preferably,

A represents formula (IIa) wherein R¹, R², R³, and R⁴ are as defined in formula (IIa),

represents a double bond,

R⁵ represents optionally substituted C_5-7 cycloalkyl, optionally substituted aryl, or optionally substituted saturated or unsaturated five- or six-membered heterocyclic group, preferably pyridyl, thienyl, isoxazole, or pyrimidyl and more preferably represents a group of formula (IIIa), formula (IIIb), or formula (IIIc), and

Z represents group (A) or group (B) wherein R⁶ represents a hydrogen atom or C_1-6 alkyl, R⁷ represents optionally substituted aryl, preferably phenyl, optionally substituted aryl C_1-6 alkyl, optionally substituted aryl C_2-6 alkenyl, or optionally substituted saturated or unsaturated five- or six-membered heterocyclic group, and R¹⁷ represents a hydrogen atom.

In formula (I-1), preferably,

A represents formula (IIb) wherein R³¹ and R³² are as defined in formula (IIb), preferably, R³¹ and R³² represent a hydrogen atom, or any one of R³¹ and R³² represents a hydrogen atom with the other representing C_1-6 alkyl optionally substituted by a halogen atom, or R³¹ and R³² together form a C_3-5 alkylene chain,

R⁵ represents optionally substituted C_5-7 cycloalkyl, optionally substituted aryl, preferably phenyl, or optionally substituted saturated or unsaturated five- or six-membered heterocyclic group, preferably pyridyl, thienyl, isoxazole, or pyrimidyl, more preferably represents a group of formula (IIIa), formula (IIIb), or formula (IIIc), and

Z represents group (A) or group (B) wherein R⁶ represents a hydrogen atom or C_1-6 alkyl, R⁷ represents optionally substituted aryl, optionally substituted aryl C_1-6 alkyl, optionally substituted aryl C_2-6 alkenyl, or optionally substituted saturated or unsaturated five- or six-membered heterocyclic group, and R¹⁷ represents a hydrogen atom.

In formula (I-1), preferably,

A represents formula (IIc) wherein R³³ and R³⁴ are as defined in formula (IIc), and, preferably, R³³ and R³⁴ represent a hydrogen atom, or any one of R³³ and R³⁴ represents a hydrogen atom with the other representing C_1-6 alkyl optionally substituted by a halogen atom, or R³³ and R³⁴ together form a C_3-5 alkylene chain,

R⁵ represents optionally substituted C_5-7 cycloalkyl, optionally substituted aryl, preferably phenyl, or optionally substituted saturated or unsaturated five- or six-membered heterocyclic group, preferably pyridyl, thienyl, isoxazole, or pyrimidyl, and more preferably, represents a group of formula (IIIa), formula (IIIb), or formula (IIIc), and

Z represents group (A) and group (B) wherein R⁶ represents a hydrogen atom or C_1-6 alkyl, R⁷ represents optionally substituted aryl, optionally substituted aryl C_1-6 alkyl, optionally substituted aryl C_2-6 alkenyl, or optionally substituted saturated or unsaturated five- or six-membered heterocyclic group, and R¹⁷ represents a hydrogen atom.

In formula (I-1), preferably,

A represents formula (IId) wherein R³⁵ and R³⁶ are as defined in formula (IId), and, preferably, R³⁵ and R³⁶ represent a hydrogen atom, or any one of R³⁵ and R³⁶ represents a hydrogen atom with the other representing C_1-6 alkyl optionally substituted by a halogen atom,

R⁵ represents optionally substituted C_5-7 cycloalkyl, optionally substituted aryl, preferably phenyl, or optionally substituted saturated or unsaturated five- or six-membered heterocyclic group, preferably pyridyl, thienyl, isoxazole, or pyrimidyl, and more preferably represents a group of formula (IIIa), formula (IIIb), or formula (IIIc),

Z represents group (A) or group (B) wherein R⁶ represents a hydrogen atom or C_1-6 alkyl, R⁷ represents optionally substituted aryl, optionally substituted aryl C_1-6 alkyl, optionally substituted aryl C_2-6 alkenyl, or optionally substituted saturated or unsaturated five- or six-membered heterocyclic group, and R¹⁷ represents a hydrogen atom.

In formula (I-1), more preferably,

A represents formula (IIa) or formula (IIa′),

wherein

(1) R¹, R², R³, and R⁴ represent a hydrogen atom,

(2) R¹ and R⁴ represent a hydrogen atom, any one of R² and R³ represents a halogen atom; hydroxyl; optionally substituted C_1-6 alkyl; optionally substituted C_1-6 alkoxy; optionally substituted mono- or di-arylamino; optionally substituted mono- or di-C_1-6 alkylamino in which the dialkylamino together may form optionally substituted cyclic amino optionally containing 1 to 3 heteroatoms; or optionally substituted mono- or di-C_2-6 alkenylamino in which the di-C_2-6 alkenylamino group together may form optionally substituted unsaturated cyclic amino optionally containing 1 to 3 heteroatoms, and the other represents a hydrogen atom,

(3) R¹ and R⁴ represent a hydrogen atom, and R² and R³, which may be the same or different, represent a halogen atom; hydroxyl; optionally substituted C_1-6 alkyl; or optionally substituted C_1-6 alkoxy,

(4) R¹ and R⁴ represent a hydrogen atom, and R² and R³ together with the carbon atoms to which they are respectively attached form a saturated or unsaturated five- to seven-membered carbocyclic ring,

(5) R¹ and R⁴ represent a hydrogen atom, any one of R² and R³ represents optionally substituted mono- or di-C_1-6 alkylamino in which the di-C_1-6 alkylamino together may form optionally substituted cyclic amino optionally containing 1 to 3 heteroatoms, and the other represents a hydrogen atom, or

(6) R¹ and R⁴ represent a hydrogen atom, any one of R² and R³ represents optionally substituted C_1-6 alkoxy, and the other represents a hydrogen atom,

R⁵ represents formula (IIIa)

wherein

(i) D, E, J, L, and M represent a carbon atom, any one or two of R⁸, R⁹, R¹⁰, R¹¹, and R¹², which may be the same or different, represent a halogen atom; hydroxymethyl; C_1-6 alkyl optionally substituted by a halogen atom; or C_1-6 alkoxy optionally substituted by a halogen atom, and the others represent a hydrogen atom,

(ii) any one or two of D, E, J, L, and M represent a nitrogen atom, and the others represent a carbon atom, any one or two of R⁸, R⁹, R¹⁰, R¹¹, and R¹² may be the same or different and represent a halogen atom; hydroxymethyl; C_1-6 alkyl optionally substituted by a halogen atom, or C_1-6 alkoxy optionally substituted by a halogen atom, and the others represent a hydrogen atom,

(iii) D, E, J, L, and M represent a carbon atom, R⁸, R⁹, and R¹² represent a hydrogen atom, any one of R¹⁰ and R¹¹ represents a group of formula (IV) wherein Q, X1, and R¹³ are as defined above, or a group of formula (V) wherein X2, X3, R¹⁴, and R¹⁵ are as defined above, and the other represents a hydrogen atom, or

(iv) any one or two of D, E, J, L, and M represent a nitrogen atom, and the others represent a carbon atom, R⁸, R⁹, and R¹² represent a hydrogen atom, and one of R¹⁰ and R¹¹ represents a group of formula (IV) wherein Q, X1, and R¹³ are as defined above, or a group of formula (V) wherein X2, X3, R¹⁴, and R¹⁵ are as defined above, and the other represents a hydrogen atom,

Z represents group (A), group (B), or group (C):

wherein

R⁶ represents a hydrogen atom or C_1-6 alkyl,

R⁷ represents optionally substituted aryl, optionally substituted aryl C_1-6 alkyl, optionally substituted aryl C_2-6 alkenyl, or optionally substituted saturated or unsaturated five- or six-membered heterocyclic group, and

R¹⁷ represents a hydrogen atom.

In formula (I-1), more preferably,

A represents formula (IIa) or formula (IIa′)

wherein

(1) R¹, R², R³, and R⁴ represent a hydrogen atom,

(2) R¹ and R⁴ represent a hydrogen atom, any one of R² and R³ represents a halogen atom; hydroxyl; optionally substituted C_1-6 alkyl; optionally substituted C_1-6 alkoxy; optionally substituted mono- or di-arylamino; optionally substituted mono- or di-C_1-6 alkylamino in which the dialkylamino together may form optionally substituted cyclic amino optionally containing 1 to 3 heteroatoms; or optionally substituted mono- or di-C_2-6 alkenylamino in which the di-C_2-6 alkenylamino group together may form optionally substituted unsaturated cyclic amino optionally containing 1 to 3 heteroatoms, and the other represents a hydrogen atom,

(3) R¹ and R⁴ represent a hydrogen atom, and R² and R³, which may be the same or different, represent a halogen atom; hydroxyl; optionally substituted C_1-6 alkyl; or optionally substituted C_1-6 alkoxy,

(4) R¹ and R⁴ represent a hydrogen atom, and R² and R³ together with the carbon atoms to which they are respectively attached form a saturated or unsaturated five- to seven-membered carbocyclic ring,

(5) R¹ and R⁴ represent a hydrogen atom, any one of R² and R³ represents optionally substituted mono- or di-C_1-6 alkylamino in which the di-C_1-6 alkylamino together may form optionally substituted cyclic amino optionally containing 1 to 3 heteroatoms, and the other represents a hydrogen atom, or

(6) R¹ and R⁴ represent a hydrogen atom, any one of R² and R³ represents optionally substituted C_1-6 alkoxy, and the other represents a hydrogen atom,

R⁵ represents formula (IIIb) or formula (IIIc)

wherein

(i) D, E, and J represent a carbon atom, G represents an oxygen or sulfur atom, any one or two of R⁸, R⁹, and R¹⁰, which may be the same or different, represent a halogen atom; hydroxymethyl; C_1-6 alkyl optionally substituted by a halogen atom; or C_1-6 alkoxy optionally substituted by a halogen atom, and the others represent a hydrogen atom, or

(ii) D, E, and J represent a carbon atom, G represents an oxygen or sulfur atom, one of R⁸, R⁹, and R¹⁰ represents a group of formula (IV) wherein Q, X1, and R¹³ are as defined above, or a group of formula (V) wherein X2, X3, R¹⁴, and R¹⁵ are as defined above, and the others represent a hydrogen atom,

Z represents group (A), group (B), or group (C):

wherein

R⁶ represents a hydrogen atom or C_1-6 alkyl,

R⁷ represents optionally substituted aryl, optionally substituted aryl C_1-6 alkyl, optionally substituted aryl C_2-6 alkenyl, or optionally substituted saturated or unsaturated five- or six-membered heterocyclic group, and

R¹⁷ represents a hydrogen atom.

In formula (I-1), more preferably,

A represents formula (IIb)

wherein

(i) R³¹ and R³² represent a hydrogen atom,

(ii) any one of R³¹ and R³² represents a hydrogen atom, and the other represents C_1-6 alkyl optionally substituted by mono- or di-C_1-6 alkylamino, which may form cyclic amino, or a halogen atom, and the cyclic amino group may contain 1 to 3 heteroatoms,

(iii) R³¹ and R³², which may be the same or different, represent C_1-6 alkyl optionally substituted by mono- or di-C_1-6 alkylamino, which may form cyclic amino, or a halogen atom, and the cyclic amino group may contain 1 to 3 heteroatoms, or

(iv) R³¹ and R³² together with the carbon atoms to which they are respectively attached form a saturated or unsaturated five- to seven-membered carbocyclic ring,

R⁵ represents formula (IIIa)

wherein

(i) D, E, J, L, and M represent a carbon atom, any one or two of R⁸, R⁹, R¹⁰, R¹¹, and R¹², which may be the same or different, represent a halogen atom; hydroxymethyl; C_1-6 alkyl optionally substituted by a halogen atom; or C_1-6 alkoxy optionally substituted by a halogen atom, and the others represent a hydrogen atom,

(ii) any one or two of D, E, J, L, and M represent a nitrogen atom, and the others represent a carbon atom, any one or two of R⁸, R⁹, R¹⁰, R¹¹, and R¹² may be the same or different and represent a halogen atom; hydroxymethyl; C_1-6 alkyl optionally substituted by a halogen atom, or C_1-6 alkoxy optionally substituted by a halogen atom, and the others represent a hydrogen atom,

(iii) D, E, J, L, and M represent a carbon atom, R⁸, R⁹, and R¹² represent a hydrogen atom, any one of R¹⁰ and R¹¹ represents a group of formula (IV) wherein Q, X1, and R¹³ are as defined above, or a group of formula (V) wherein X2, X3, R¹⁴, and R¹⁵ are as defined above, and the other represents a hydrogen atom, or

(iv) any one or two of D, E, J, L, and M represent a nitrogen atom, and the others represent a carbon atom, R⁸, R⁹, and R¹² represent a hydrogen atom, and one of R¹⁰ and R¹¹ represents a group of formula (IV) wherein Q, X1, and R¹³ are as defined above, or a group of formula (V) wherein X2, X3, R¹⁴, and R¹⁵ are as defined above, and the other represents a hydrogen atom,

Z represents group (A), group (B), or group (C):

wherein

R⁶ represents a hydrogen atom or C_1-6 alkyl,

R⁷ represents optionally substituted aryl, optionally substituted aryl C_1-6 alkyl, optionally substituted aryl C_2-6 alkenyl, or optionally substituted saturated or unsaturated five- or six-membered heterocyclic group, and

R¹⁷ represents a hydrogen atom.

In formula (I-1), more preferably,

A represents formula (IIb)

wherein

(i) R³¹ and R³² represent a hydrogen atom,

(ii) any one of R³¹ and R³² represents a hydrogen atom, and the other represents C_1-6 alkyl optionally substituted by mono- or di-C_1-6 alkylamino, which may form cyclic amino, or a halogen atom, and the cyclic amino group may contain 1 to 3 heteroatoms,

(iii) R³¹ and R³², which may be the same or different, represent C_1-6 alkyl optionally substituted by mono- or di-C_1-6 alkylamino, which may form cyclic amino, or a halogen atom, and the cyclic amino group may contain 1 to 3 heteroatoms, or

(iv) R³¹ and R³² together with the carbon atoms to which they are respectively attached form a saturated or unsaturated five- to seven-membered carbocyclic ring,

R⁵ represents formula (IIIb) or formula (IIIc)

wherein

(i) D, E, and J represent a carbon atom, G represents an oxygen or sulfur atom, any one or two of R⁸, R⁹, and R¹⁰, which may be the same or different, represent a halogen atom; hydroxymethyl; C_1-6 alkyl optionally substituted by a halogen atom; or C_1-6 alkoxy optionally substituted by a halogen atom, and the others represent a hydrogen atom, or

(ii) D, E, and J represent a carbon atom, G represents an oxygen or sulfur atom, one of R⁸, R⁹, and R¹⁰ represents a group of formula (IV) wherein Q, X1, and R¹³ are as defined above, or a group of formula (V) wherein X2, X3, R¹⁴, and R¹⁵ are as defined above, and the others represent a hydrogen atom,

Z represents group (A), group (B), or group (C):

wherein

R⁶ represents a hydrogen atom or C_1-6 alkyl,

R⁷ represents optionally substituted aryl, optionally substituted aryl C_1-6 alkyl, optionally substituted aryl C_2-6 alkenyl, or optionally substituted saturated or unsaturated five- or six-membered heterocyclic group, and

R¹⁷ represents a hydrogen atom.

In formula (I-1), more preferably,

A represents formula (IIc)

wherein

(i) R³³ and R³⁴ represent a hydrogen atom,

(ii) any one of R³³ and R³⁴ represents a hydrogen atom, and the other represents C_1-6 alkyl optionally substituted by mono- or di-C_1-6 alkylamino, which may form cyclic amino, or a halogen atom, and the cyclic amino group may contain 1 to 3 heteroatoms,

(iii) R³³ and R³⁴, which may be the same or different, represent C_1-6 alkyl optionally substituted by mono- or di-C_1-6 alkylamino, which may form cyclic amino, or a halogen atom, and the cyclic amino group may contain 1 to 3 heteroatoms, or

(iv) R³³ and R³⁴ together with the carbon atoms to which they are respectively attached form a saturated or unsaturated five- to seven-membered carbocyclic ring,

R⁵ represents formula (IIIa)

wherein

(i) D, E, J, L, and M represent a carbon atom, any one or two of R⁸, R⁹, R¹⁰, R¹¹, and R¹², which may be the same or different, represent a halogen atom; hydroxymethyl; C_1-6 alkyl optionally substituted by a halogen atom; or C_1-6 alkoxy optionally substituted by a halogen atom, and the others represent a hydrogen atom,

(ii) any one or two of D, E, J, L, and M represent a nitrogen atom, and the others represent a carbon atom, any one or two of R⁸, R⁹, R¹⁰, R¹¹, and R¹² may be the same or different and represent a halogen atom; hydroxymethyl; C_1-6 alkyl optionally substituted by a halogen atom, or C_1-6 alkoxy optionally substituted by a halogen atom, and the others represent a hydrogen atom,

(iii) D, E, J, L, and M represent a carbon atom, R⁸, R⁹, and R¹² represent a hydrogen atom, any one of R¹⁰ and R¹¹ represents a group of formula (IV) wherein Q, X1, and R¹³ are as defined above, or a group of formula (V) wherein X2, X3, R¹⁴, and R¹⁵ are as defined above, and the other represents a hydrogen atom, or

(iv) any one or two of D, E, J, L, and M represent a nitrogen atom, and the others represent a carbon atom, R⁸, R⁹, and R¹² represent a hydrogen atom, and one of R¹⁰ and R¹¹ represents a group of formula (IV) wherein Q, X1, and R¹³ are as defined above, or a group of formula (V) wherein X2, X3, R¹⁴, and R¹⁵ are as defined above, and the other represents a hydrogen atom,

Z represents group (A), group (B), or group (C):

wherein

R⁶ represents a hydrogen atom or C_1-6 alkyl,

R⁷ represents optionally substituted aryl, optionally substituted aryl C_1-6 alkyl, optionally substituted aryl C_2-6 alkenyl, or optionally substituted saturated or unsaturated five- or six-membered heterocyclic group, and

R¹⁷ represents a hydrogen atom.

In formula (I-1), more preferably,

A represents formula (IIc)

wherein

(i) R³³ and R³⁴ represent a hydrogen atom,

(ii) any one of R³³ and R³⁴ represents a hydrogen atom, and the other represents C_1-6 alkyl optionally substituted by mono- or di-C_1-6 alkylamino, which may form cyclic amino, or a halogen atom, and the cyclic amino group may contain 1 to 3 heteroatoms,

(iii) R³³ and R³⁴, which may be the same or different, represent C_1-6 alkyl optionally substituted by mono- or di-C_1-6 alkylamino, which may form cyclic amino, or a halogen atom, and the cyclic amino group may contain 1 to 3 heteroatoms, or

(iv) R³³ and R³⁴ together with the carbon atoms to which they are respectively attached form a saturated or unsaturated five- to seven-membered carbocyclic ring,

R⁵ represents formula (IIIb) or formula (IIIc)

wherein

(i) D, E, and J represent a carbon atom, G represents an oxygen or sulfur atom, any one or two of R⁸, R⁹, and R¹⁰, which may be the same or different, represent a halogen atom; hydroxymethyl; C_1-6 alkyl optionally substituted by a halogen atom; or C_1-6 alkoxy optionally substituted by a halogen atom, and the others represent a hydrogen atom, or

(ii) D, E, and J represent a carbon atom, G represents an oxygen or sulfur atom, one of R⁸, R⁹, and R¹⁰ represents a group of formula (IV) wherein Q, X1, and R¹³ are as defined above, or a group of formula (V) wherein X2, X3, R¹⁴, and R¹⁵ are as defined above, and the others represent a hydrogen atom,

Z represents group (A), group (B), or group (C):

wherein

R⁶ represents a hydrogen atom or C_1-6 alkyl,

R⁷ represents optionally substituted aryl, optionally substituted aryl C_1-6 alkyl, optionally substituted aryl C_2-6 alkenyl, or optionally substituted saturated or unsaturated five- or six-membered heterocyclic group, and

R¹⁷ represents a hydrogen atom.

In formula (I-1), more preferably,

A represents formula (IId)

wherein R³⁵ and R³⁶ represent a hydrogen atom, or any one of R³⁵ and R³⁶ represents a hydrogen atom with the other representing C_1-6 alkyl optionally substituted by a halogen atom,

R⁵ represents formula (IIIa)

wherein

(i) D, E, J, L, and M represent a carbon atom, any one or two of R⁸, R⁹, R¹⁰, R¹¹, and R¹², which may be the same or different, represent a halogen atom; hydroxymethyl; C_1-6 alkyl optionally substituted by a halogen atom; or C_1-6 alkoxy optionally substituted by a halogen atom, and the others represent a hydrogen atom,

(ii) any one or two of D, E, J, L, and M represent a nitrogen atom, and the others represent a carbon atom, any one or two of R⁸, R⁹, R¹⁰, R¹¹, and R¹² may be the same or different and represent a halogen atom; hydroxymethyl; C_1-6 alkyl optionally substituted by a halogen atom, or C_1-6 alkoxy optionally substituted by a halogen atom, and the others represent a hydrogen atom,

(iii) D, E, J, L, and M represent a carbon atom, R⁸, R⁹, and R¹² represent a hydrogen atom, any one of R¹⁰ and R¹¹ represents a group of formula (IV) wherein Q, X1, and R¹³ are as defined above, or a group of formula (V) wherein X2, X3, R¹⁴, and R¹⁵ are as defined above, and the other represents a hydrogen atom, or

(iv) any one or two of D, E, J, L, and M represent a nitrogen atom, and the others represent a carbon atom, R⁸, R⁹, and R¹² represent a hydrogen atom, and one of R¹⁰ and R¹¹ represents a group of formula (IV) wherein Q, X1, and R¹³ are as defined above, or a group of formula (V) wherein X2, X3, R¹⁴, and R¹⁵ are as defined above, and the other represents a hydrogen atom,

Z represents group (A), group (B), or group (C):

wherein

R⁶ represents a hydrogen atom or C_1-6 alkyl,

R⁷ represents optionally substituted aryl, optionally substituted aryl C_1-6 alkyl, optionally substituted aryl C_2-6 alkenyl, or optionally substituted saturated or unsaturated five- or six-membered heterocyclic group, and

R¹⁷ represents a hydrogen atom.

In formula (I-1), more preferably,

A represents formula (IId)

wherein R³⁵ and R³⁶ represent a hydrogen atom, or any one of R³⁵ and R³⁶ represents a hydrogen atom with the other representing C_1-6 alkyl optionally substituted by a halogen atom,

R⁵ represents formula (IIIb) or formula (IIIc)

wherein

(i) D, E, and J represent a carbon atom, G represents an oxygen or sulfur atom, any one or two of R⁸, R⁹, and R¹⁰, which may be the same or different, represent a halogen atom; hydroxymethyl; C_1-6 alkyl optionally substituted by a halogen atom; or C_1-6 alkoxy optionally substituted by a halogen atom, and the others represent a hydrogen atom, or

(ii) D, E, and J represent a carbon atom, G represents an oxygen or sulfur atom, one of R⁸, R⁹, and R¹⁰ represents a group of formula (IV) wherein Q, X1, and R¹³ are as defined above, or a group of formula (V) wherein X2, X3, R¹⁴, and R¹⁵ are as defined above, and the others represent a hydrogen atom,

Z represents group (A), group (B), or group (C):

wherein

R⁶ represents a hydrogen atom or C_1-6 alkyl,

R⁷ represents optionally substituted aryl, optionally substituted aryl C_1-6 alkyl, optionally substituted aryl C_2-6 alkenyl, or optionally substituted saturated or unsaturated five- or six-membered heterocyclic group, and

R¹⁷ represents a hydrogen atom.

Among the compounds of formula (I), quinazolone derivatives may be represented by formula (I-2). wherein A, R⁵, Z, and are as defined in formula (I).

In formula (I-2), preferably,

A represents formula (IIa) or formula (IIa′) wherein R¹, R², R³, and R⁴ are as defined in formula (IIa) and formula (IIa′) and are preferably the same or different and represent a hydrogen atom; a halogen atom; hydroxyl; optionally substituted C_1-6 alkyl; or optionally substituted C_1-6 alkoxy,

R⁵ represents optionally substituted C_5-7 cycloalkyl, optionally substituted aryl, preferably phenyl, or optionally substituted saturated or unsaturated five- or six-membered heterocyclic group, preferably pyridyl, thienyl, isoxazole, or pyrimidyl and more preferably represents a group of formula (IIIa), formula (IIIb) or formula (IIIc).

Z represents group (A), group (B), or group (C) wherein R⁶ represents a hydrogen atom or C_1-6 alkyl, R⁷ represents optionally substituted aryl, preferably, phenyl, or naphthyl, optionally substituted aryl, preferably phenyl, or naphthyl, C_1-6 alkyl, optionally substituted aryl, preferably phenyl, or naphthyl, C_2-6 alkenyl, or optionally substituted saturated or unsaturated five- or six-membered heterocyclic group, preferably furyl, thienyl, pyrrolyl, or pyridyl, and R¹⁷ represents a hydrogen atom.

In formula (I-2), preferably,

A represents formula (IIa) wherein R¹, R², R³, and R⁴ are as defined in formula (IIa),

represents a double bond,

R⁵ represents optionally substituted C_5-7 cycloalkyl, optionally substituted aryl, or optionally substituted saturated or unsaturated five- or six-membered heterocyclic group, preferably pyridyl, thienyl, isoxazole, or pyrimidyl and more preferably represents a group of formula (IIIa), formula (IIIb), or formula (IIIc).

Z represents group (A) or group (B) wherein R⁶ represents a hydrogen atom or C_1-6 alkyl, R⁷ represents optionally substituted aryl, preferably phenyl, optionally substituted aryl C_1-6 alkyl, optionally substituted aryl C_2-6 alkenyl, or optionally substituted saturated or unsaturated five- or six-membered heterocyclic group, and R¹⁷ represents a hydrogen atom.

In formula (I-2), preferably,

A represents formula (IIb) wherein R³¹ and R³² are as defined in formula (IIb), preferably, R³¹ and R³² represent a hydrogen atom, or any one of R³¹ and R³² represents a hydrogen atom with the other representing C_1-6 alkyl optionally substituted by a halogen atom, or R³¹ and R³² together may form a C_3-5 alkylene chain,

R⁵ represents optionally substituted C_5-7 cycloalkyl, optionally substituted aryl, preferably phenyl, or optionally substituted saturated or unsaturated five- or six-membered heterocyclic group, preferably pyridyl, thienyl, isoxazole, or pyrimidyl, more preferably a group of formula (IIIa), formula (IIIb), or formula (IIIc), and

Z represents group (A) or group (B) wherein R⁶ repersents a hydrogen atom or C_1-6 alkyl, R⁷ represents optionally substituted aryl, optionally substituted aryl C_1-6 alkyl, optionally substituted aryl C_2-6 alkenyl, or optionally substituted saturated or unsaturated five- or six-membered heterocyclic group, and R¹⁷ represents a hydrogen atom.

In formula (I-2), preferably,

A represents formula (IIc) wherein R³³ and R³⁴ are as defined in formula (IIc), and, preferably, R³³ and R³⁴ represent a hydrogen atom, or any one of R³³ and R³⁴ represents a hydrogen atom with the other representing C_1-6 alkyl optionally substituted by a halogen atom, or R³³ and R³⁴ together form a C_3-5 alkylene chain,

R⁵ represents optionally substituted C_5-7 cycloalkyl, optionally substituted aryl, preferably phenyl, or optionally substituted saturated or unsaturated five- or six-membered heterocyclic group, preferably pyridyl, thienyl, isoxazole, or pyrimidyl, more preferably a group of formula (IIIa), formula (IIIb), or formula (IIIc), and

Z represents group (A) and group (B) wherein R⁶ represents a hydrogen atom or C_1-6 alkyl, R⁷ represents optionally substituted aryl, optionally substituted aryl C_1-6 alkyl, optionally substituted aryl C_2-6 alkenyl, or optionally substituted saturated or unsaturated five- or six-membered heterocyclic group, and R¹⁷ represents a hydrogen atom.

In formula (I-2), preferably,

A represents formula (IId) wherein R³⁵ and R³⁶ are as defined in formula (IId), and R³⁵ and R³⁶ represent a hydrogen atom, or any one of R³⁵ and R³⁶ represents a hydrogen atom with the other representing C_1-6 alkyl optionally substituted by a halogen atom,

R⁵ represents optionally substituted C_5-7 cycloalkyl, optionally substituted aryl, preferably phenyl, or optionally substituted saturated or unsaturated five- or six-membered heterocyclic group, preferably pyridyl, thienyl, isoxazole, or pyrimidyl, more preferably a group of formula (IIIa), formula (IIIb), or formula (IIIc),

Z represents group (A) or group (B) wherein R⁶ represents a hydrogen atom or C_1-6 alkyl, R⁷ represents optionally substituted aryl, optionally substituted aryl C_1-6 alkyl, optionally substituted aryl C_2-6 alkenyl, or optionally substituted saturated or unsaturated five- or six-membered heterocyclic group, and R¹⁷ represents a hydrogen atom.

In formula (I-2), more preferably,

A represents formula (IIa) or formula (IIa′),

wherein

(1) R¹, R², R³, and R⁴ represent a hydrogen atom,

(2) R¹ and R⁴ represent a hydrogen atom, any one of R² and R³ represents a halogen atom; hydroxyl; optionally substituted C_1-6 alkyl; optionally substituted C_1-6 alkoxy; optionally substituted mono- or di-arylamino; optionally substituted mono- or di-C_1-6 alkylamino in which the dialkylamino together may form optionally substituted cyclic amino optionally containing 1 to 3 heteroatoms; or optionally substituted mono- or di-C_2-6 alkenylamino in which the di-C_2-6 alkenylamino group together may form optionally substituted unsaturated cyclic amino optionally cantaining 1 to 3 heteroatoms, and the other represents a hydrogen atom,

(3) R¹ and R⁴ represent a hydrogen atom, and R² and R³, which may be the same or different, represent a halogen atom; hydroxyl; optionally substituted C_1-6 alkyl; or optionally substituted C_1-6 alkoxy,

(4) R¹ and R⁴ represent a hydrogen atom, and R² and R³ together with the carbon atoms to which they are respectively attached form a saturated or unsaturated five- to seven-membered carbocyclic ring,

(5) R¹ and R⁴ represent a hydrogen atom, any one of R² and R³ represents optionally substituted mono- or di-C_1-6 alkylamino in which the di-C_1-6 alkylamino together may form optionally substituted cyclic amino optionally containing 1 to 3 heteroatoms, and the other represents a hydrogen atom, or

(6) R¹ and R⁴ represent a hydrogen atom, any one of R² and R³ represents optionally substituted C_1-6 alkoxy, and the other represents a hydrogen atom,

R⁵ represents formula (IIIa)

wherein

(i) D, E, J, L, and M represent a carbon atom, any one or two of R⁸, R⁹, R¹⁰, R¹¹, and R¹², which may be the same or different, represent a halogen atom; hydroxymethyl; C_1-6 alkyl optionally substituted by a halogen atom; or C_1-6 alkoxy optionally substituted by a halogen atom, and the others represent a hydrogen atom,

(ii) any one or two of D, E, J, L, and M represent a nitrogen atom, and the others represent a carbon atom, any one or two of R⁸, R⁹, R¹⁰, R¹¹, and R¹² may be the same or different and represent a halogen atom; hydroxymethyl; C_1-6 alkyl optionally substituted by a halogen atom, or C_1-6 alkoxy optionally substituted by a halogen atom, and the others represent a hydrogen atom,

(iii) D, E, J, L, and M represent a carbon atom, R⁸, R⁹, and R¹² represent a hydrogen atom, any one of R¹⁰ and R¹¹ represents a group of formula (IV) wherein Q, X1, and R¹³ are as defined above, or a group of formula (V) wherein X2, X3, R¹⁴, and R¹⁵ are as defined above, and the other represents a hydrogen atom,

(iv) any one or two of D, E, J, L, and M represent a nitrogen atom, and the others represent a carbon atom, R⁸, R⁹, and R¹² represent a hydrogen atom, and one of R¹⁰ and R¹¹ represents a group of formula (IV) wherein Q, X1, and R¹³ are as defined above, or a group of formula (V) wherein X2, X3, R¹⁴, and R¹⁵ are as defined above, and the other represents a hydrogen atom,

Z represents group (A), group (B), or group (C):

wherein

R⁶ represents a hydrogen atom or C_1-6 alkyl,

R⁷ represents optionally substituted aryl, optionally substituted aryl C_1-6 alkyl, optionally substituted aryl C_2-6 alkenyl, or optionally substituted saturated or unsaturated five- or six-membered heterocyclic group, and

R¹⁷ represents a hydrogen atom.

In formula (I-2), more preferably,

A represents formula (IIa) or formula (IIa′)

wherein

(1) R¹, R², R³, and R⁴ represent a hydrogen atom,

(2) R¹ and R⁴ represent a hydrogen atom, any one of R² and R³ represents a halogen atom; hydroxyl; optionally substituted C_1-6 alkyl; optionally substituted C_1-6 alkoxy; optionally substituted mono- or di-arylamino; optionally substituted mono- or di-C_1-6 alkylamino in which the dialkylamino together may form optionally substituted cyclic amino optionally containing 1 to 3 heteroatoms; or optionally substituted mono- or di-C_2-6 alkenylamino in which the di-C_2-6 alkenylamino group together may form optionally substituted unsaturated cyclic amino optionally containing 1 to 3 heteroatoms, and the other represents a hydrogen atom,

(3) R¹ and R⁴ represent a hydrogen atom, and R² and R³, which may be the same or different, represent a halogen atom; hydroxyl; optionally substituted C_1-6 alkyl; or optionally substituted C_1-6 alkoxy,

(4) R¹ and R⁴ represent a hydrogen atom, and R² and R³ together with the carbon atoms to which they are respectively attached form a saturated or unsaturated five- to seven-membered carbocyclic ring,

(5) R¹ and R⁴ represent a hydrogen atom, any one of R² and R³ represents optionally substituted mono- or di-C_1-6 alkylamino in which the di-C_1-6 alkylamino together may form optionally substituted cyclic amino optionally containing 1 to 3 heteroatoms, and the other represents a hydrogen atom, or

(6) R¹ and R⁴ represent a hydrogen atom, any one of R² and R³ represents optionally substituted C_1-6 alkoxy, and the other represents a hydrogen atom,

R⁵ represents formula (IIIb) or formula (IIIc)

wherein

(i) D, E, and J represent a carbon atom, G represents an oxygen or sulfur atom, any one or two of R⁸, R⁹, and R¹⁰, which may be the same or different, represent a halogen atom; hydroxymethyl; C_1-6 alkyl optionally substituted by a halogen atom; or C_1-6 alkoxy optionally substituted by a halogen atom, and the others represent a hydrogen atom, or

(ii) D, E, and J represent a carbon atom, G represents an oxygen or sulfur atom, one of R⁸, R⁹, and R¹⁰ represents a group of formula (IV) wherein Q, X1, and R¹³ are as defined above, or a group of formula (V) wherein X2, X3, R¹⁴, and R¹⁵ are as defined above, and the others represent a hydrogen atom,

Z represents group (A), group (B), or group (C):

wherein

R⁶ represents a hydrogen atom or C_1-6 alkyl,

R⁷ represents optionally substituted aryl, optionally substituted aryl C_1-6 alkyl, optionally substituted aryl C_2-6 alkenyl, or optionally substituted saturated or unsaturated five- or six-membered heterocyclic group, and

R¹⁷ represents a hydrogen atom.

In formula (I-2), more preferably,

A represents formula (IIb)

wherein

(i) R³¹ and R³² represent a hydrogen atom,

(ii) any one of R³¹ and R³² represents a hydrogen atom, and the other represents C_1-6 alkyl optionally substituted by mono- or di-C_1-6 alkylamino, which may form cyclic amino, or a halogen atom, and the cyclic amino group may contain 1 to 3 heteroatoms,

(iii) R³¹ and R³², which may be the same or different, represent C_1-6 alkyl optionally substituted by mono- or di-C_1-6 alkylamino, which may form cyclic amino, or a halogen atom, and the cyclic amino group may contain 1 to 3 heteroatoms, or

(iv) R³¹ and R³² together with the carbon atoms to which they are respectively attached form a saturated or unsaturated five- to seven-membered carbocyclic ring,

R⁵ represents formula (IIIa)

wherein

(i) D, E, J, L, and M represent a carbon atom, any one or two of R⁸, R⁹, R¹⁰, R¹¹, and R¹², which may be the same or different, represent a halogen atom; hydroxymethyl; C_1-6 alkyl optionally substituted by a halogen atom; or C_1-6 alkoxy optionally substituted by a halogen atom, and the others represent a hydrogen atom,

(ii) any one or two of D, E, J, L, and M represent a nitrogen atom, and the others represent a carbon atom, any one or two of R⁸, R⁹, R¹⁰, R¹¹, and R¹² may be the same or different and represent a halogen atom; hydroxymethyl; C_1-6 alkyl optionally substituted by a halogen atom, or C_1-6 alkoxy optionally substituted by a halogen atom, and the others represent a hydrogen atom,

(iii) D, E, J, L, and M represent a carbon atom, R⁸, R⁹, and R¹² represent a hydrogen atom, any one of R¹⁰ and R¹¹ represents a group of formula (IV) wherein Q, X1, and R¹³ are as defined above, or a group of formula (V) wherein X2, X3, R¹⁴, and R¹⁵ are as defined above, and the other represents a hydrogen atom, or

(iv) any one or two of D, E, J, L, and M represent a nitrogen atom, and the others represent a carbon atom, R⁸, R⁹, and R¹² represent a hydrogen atom, and one of R¹⁰ and R¹¹ represents a group of formula (IV) wherein Q, X1, and R¹³ are as defined above, or a group of formula (V) wherein X2, X3, R¹⁴, and R¹⁵ are as defined in above, and the other represents a hydrogen atom,

Z represents group (A), group (B), or group (C):

wherein

R⁶ represents a hydrogen atom or C_1-6 alkyl,

R⁷ represents optionally substituted aryl, optionally substituted aryl C_1-6 alkyl, optionally substituted aryl C_2-6 alkenyl, or optionally substituted saturated or unsaturated five- or six-membered heterocyclic group, and

R¹⁷ represents a hydrogen atom.

In formula (I-2), more preferably,

A represents formula (IIb)

wherein

(i) R³¹ and R³² represent a hydrogen atom,

(ii) any one of R³¹ and R³² represents a hydrogen atom, and the other represents C_1-6 alkyl optionally substituted by mono- or di-C_1-6 alkylamino, which may form cyclic amino, or a halogen atom, and the cyclic amino group may contain 1 to 3 heteroatoms,

(iii) R³¹ and R³², which may be the same or different, represent C_1-6 alkyl optionally substituted by mono- or di-C_1-6 alkylamino, which may form cyclic amino, or a halogen atom, and the cyclic amino group may contain 1 to 3 heteroatoms, or

(iv) R³¹ and R³² together with the carbon atoms to which they are respectively attached form a saturated or unsaturated five- to seven-membered carbocyclic ring,

R⁵ represents formula (IIIb) or formula (IIIc)

wherein

(i) D, E, and J represent a carbon atom, G represents an oxygen or sulfur atom, any one or two of R⁸, R⁹, and R¹⁰, which may be the same or different, represent a halogen atom; hydroxymethyl; C_1-6 alkyl optionally substituted by a halogen atom; or C_1-6 alkoxy optionally substituted by a halogen atom, and the others represent a hydrogen atom, or

(ii) D, E, and J represent a carbon atom, G represents an oxygen or sulfur atom, one of R⁸, R⁹, and R¹⁰ represents a group of formula (IV) wherein Q, X1, and R¹³ are as defined above, or a group of formula (V) wherein X2, X3, R¹⁴, and R¹⁵ are as defined above, and the others represent a hydrogen atom,

Z represents group (A), group (B), or group (C):

wherein

R⁶ represents a hydrogen atom or C_1-6 alkyl,

R⁷ represents optionally substituted aryl, optionally substituted aryl C_1-6 alkyl, optionally substituted aryl C_2-6 alkenyl, or optionally substituted saturated or unsaturated five- or six-membered heterocyclic group, and

R¹⁷ represents a hydrogen atom.

In formula (I-2), more preferably,

A represents formula (IIc)

wherein

(i) R³³ and R³⁴ represent a hydrogen atom,

(ii) any one of R³³ and R³⁴ represents a hydrogen atom, and the other represents C_1-6 alkyl optionally substituted by mono- or di-C_1-6 alkylamino, which may form cyclic amino, or a halogen atom, and the cyclic amino group may contain 1 to 3 heteroatoms,

(iii) R³³ and R³⁴, which may be the same or different, represent C_1-6 alkyl optionally substituted by mono- or di-C_1-6 alkylamino, which may form cyclic amino, or a halogen atom, and the cyclic amino group may contain 1 to 3 heteroatoms, or

(iv) R³³ and R³⁴ together with the carbon atoms to which they are respectively attached form a saturated or unsaturated five- to seven-membered carbocyclic ring,

R⁵ represents formula (IIIa)

wherein

(i) D, E, J, L, and M represent a carbon atom, any one or two of R⁸, R⁹, R¹⁰, R¹¹, and R¹², which may be the same or different, represent a halogen atom; hydroxymethyl; C_1-6 alkyl optionally substituted by a halogen atom; or C_1-6 alkoxy optionally substituted by a halogen atom, and the others represent a hydrogen atom,

(ii) any one or two of D, E, J, L, and M represent a nitrogen atom, and the others represent a carbon atom, any one or two of R⁸, R⁹, R¹⁰, R¹¹, and R¹² may be the same or different and represent a halogen atom; hydroxymethyl; C_1-6 alkyl optionally substituted by a halogen atom, or C_1-6 alkoxy optionally substituted by a halogen atom, and the others represent a hydrogen atom,

(iii) D, E, J, L, and M represent a carbon atom, R⁸, R⁹, and R¹² represent a hydrogen atom, any one of R¹⁰ and R¹¹ represents a group of formula (IV) wherein Q, X1, and R¹³ are as defined above, or a group of formula (V) wherein X2, X3, R¹⁴, and R¹⁵ are as defined above, and the other represents a hydrogen atom, or

(iv) any one or two of D, E, J, L, and M represent a nitrogen atom, and the others represent a carbon atom, R⁸, R⁹, and R¹² represent a hydrogen atom, and one of R¹⁰ and R¹¹ represents a group of formula (IV) wherein Q, X1, and R¹³ are as defined above, or a group of formula (V) wherein X2, X3, R¹⁴, and R¹⁵ are as defined above, and the other represents a hydrogen atom,

Z represents group (A), group (B), or group (C):

wherein

R⁶ represents a hydrogen atom or C_1-6 alkyl,

R⁷ represents optionally substituted aryl, optionally substituted aryl C_1-6 alkyl, optionally substituted aryl C_2-6 alkenyl, or optionally substituted saturated or unsaturated five- or six-membered heterocyclic group, and

R¹⁷ represents a hydrogen atom.

In formula (I-2), more preferably,

A represents formula (IIc)

wherein

(i) R³³ and R³⁴ represent a hydrogen atom,

(ii) any one of R³³ and R³⁴ represents a hydrogen atom, and the other represents C_1-6 alkyl optionally substituted by mono- or di-C_1-6 alkylamino, which may form cyclic amino, or a halogen atom, and the cyclic amino group may contain 1 to 3 heteroatoms,

(iii) R³³ and R³⁴, which may be the same or different, represent C_1-6 alkyl optionally substituted by mono- or di-C_1-6 alkylamino, which may form cyclic amino, or a halogen atom, and the cyclic amino group may contain 1 to 3 heteroatoms, or

(iv) R³³ and R³⁴ together with the carbon atoms to which they are respectively attached form a saturated or unsaturated five- to seven-membered carbocyclic ring,

R⁵ represents formula (IIIb) or formula (IIIc)

wherein

(i) D, E, and J represent a carbon atom, G represents an oxygen or sulfur atom, any one or two of R⁸, R⁹, and R¹⁰, which may be the same or different, represent a halogen atom; hydroxymethyl; C_1-6 alkyl optionally substituted by a halogen atom; or C_1-6 alkoxy optionally substituted by a halogen atom, and the others represent a hydrogen atom, or

(ii) D, E, and J represent a carbon atom, G represents an oxygen or sulfur atom, one of R⁸, R⁹, and R¹⁰ represents a group of formula (IV) wherein Q, X1, and R¹³ are as defined above, or a group of formula (V) wherein X2, X3, R⁴, and R¹⁵ are as defined above, and the others represent a hydrogen atom,

Z represents group (A), group (B), or group (C):

wherein

R⁶ represents a hydrogen atom or C_1-6 alkyl,

R⁷ represents optionally substituted aryl, optionally substituted aryl C_1-6 alkyl, optionally substituted aryl C_2-6 alkenyl, or optionally substituted saturated or unsaturated five- or six-membered heterocyclic group, and

R¹⁷ represents a hydrogen atom.

In formula (I-2), more preferably,

A represents formula (IId)

wherein R³⁵ and R³⁶ represent a hydrogen atom, or any one of R³⁵ and R³⁶ represents a hydrogen atom with the other representing C_1-6 alkyl optionally substituted by a halogen atom,

R⁵ represents formula (IIIa)

wherein

(i) D, E, J, L, and M represent a carbon atom, any one or two of R⁸, R⁹, R¹⁰, R¹¹, and R¹², which may be the same or different, represent a halogen atom; hydroxymethyl; C_1-6 alkyl optionally substituted by a halogen atom; or C_1-6 alkoxy optionally substituted by a halogen atom, and the others represent a hydrogen atom,

(ii) any one or two of D, E, J, L, and M represent a nitrogen atom, and the others represent a carbon atom, any one or two of R⁸, R⁹, R¹⁰, R¹¹, and R¹² may be the same or different and represent a halogen atom; hydroxymethyl; C_1-6 alkyl optionally substituted by a halogen atom, or C_1-6 alkoxy optionally substituted by a halogen atom, and the others represent a hydrogen atom,

(iii) D, E, J, L, and M represent a carbon atom, R⁸, R⁹, and R¹² represent a hydrogen atom, any one of R¹⁰ and R¹¹ represents a group of formula (IV) wherein Q, X1, and R¹³ are as defined above, or a group of formula (V) wherein X2, X3, R¹⁴, and R¹⁵ are as defined above, and the other represents a hydrogen atom, or

(iv) any one or two of D, E, J, L, and M represent a nitrogen atom, and the others represent a carbon atom, R⁸, R⁹, and R¹² represent a hydrogen atom, and one of R¹⁰ and R¹¹ represents a group of formula (IV) wherein Q, X1, and R¹³ are as defined above, or a group of formula (V) wherein X2, X3, R¹⁴, and R¹⁵ are as defined above, and the other represents a hydrogen atom,

Z represents group (A), group (B), or group (C):

wherein

R⁶ represents a hydrogen atom or C_1-6 alkyl,

R⁷ represents optionally substituted aryl, optionally substituted aryl C_1-6 alkyl, optionally substituted aryl C_2-6 alkenyl, or optionally substituted saturated or unsaturated five- or six-membered heterocyclic group, and

R¹⁷ represents a hydrogen atom.

In formula (I-2), more preferably,

A represents formula (IId)

wherein R³⁵ and R³⁶ represent a hydrogen atom, or any one of R³⁵ and R³⁶ represents a hydrogen atom with the other representing C_1-6 alkyl optionally substituted by a halogen atom,

R⁵ represents formula (IIIb) or formula (IIIc)

wherein

(i) D, E, and J represent a carbon atom, G represents an oxygen or sulfur atom, any one or two of R⁸, R⁹, and R¹⁰, which may be the same or different, represent a halogen atom; hydroxymethyl; C_1-6 alkyl optionally substituted by a halogen atom; or C_1-6 alkoxy optionally substituted by a halogen atom, and the others represent a hydrogen atom, or

(ii) D, E, and J represent a carbon atom, G represents an oxygen or sulfur atom, one of R⁸, R⁹, and R¹⁰ represents a group of formula (IV) wherein Q, X1, and R¹³ are as defined above, or a group of formula (V) wherein X2, X3, R¹⁴, and R¹⁵ are as defined above, and the others represent a hydrogen atom,

Z represents group (A), group (B), or group (C):

wherein

R⁶ represents a hydrogen atom or C_1-6 alkyl,

R⁷ represents optionally substituted aryl, optionally substituted aryl C_1-6 alkyl, optionally substituted aryl C_2-6 alkenyl, or optionally substituted saturated or unsaturated five- or six-membered heterocyclic group, and

R¹⁷ represents a hydrogen atom.

Examples of preferred compounds according to the present invention include compounds 1 to 1077 described in the Examples.

Compounds of formula (I) according to the present invention include compounds wherein

A represents a five- to nine-membered unsaturated carbocyclic moiety or a five- to nine-membered unsaturated heterocyclic moiety, and represents a double bond,

the carbocyclic moiety and heterocyclic moiety represented by A are optionally substituted by

(a) a halogen atom;

(b) hydroxyl;

(c) C_1-6 alkyl;

(d) C_1-6 alkoxy;

(e) aryl;

(f) aryloxy;

(g) arylthio;

(h) alkylthio;

(i) nitro; or

(j) amino,

(c) the C_1-6 alkyl group, (d) the C_1-6 alkoxy group, (e) the aryl group, (f) the aryloxy group, (g) the arylthio group, and (h) the alkylthio group are optionally substituted by (1) hydroxyl, (2) thiol, (3) amino, (4) C_1-6 alkoxy, (5) C_1-6 alkylthio, (6) C_1-6 alkylsulfonyl, (7) mono- or di-C_1-6 alkylamino in which the di-C_1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms, (8) aryloxy, (9) arylthio, (10) arylsulfonyl, (11) aryl, (12) a heterocyclic group, (13) a halogen atom, or (14) arylamino in which the amino group is optionally substituted by C_1-6 alkyl, and the aryl group is optionally substituted by a halogen atom, C_1-6 alkyl, C_1-6 alkoxy, or C_1-6 alkylamino,

when the carbocyclic moiety and the heterocyclic moiety are substituted by two (c) C_1-6 alkyl groups, they together may form a C_3-5 alkylene chain,

R⁵ represents C_1-6 alkyl, aryl, C_1-6 alkoxy, aryloxy, C_1-6 alkylamino, arylamino, C_1-6 alkylthio, arylthio, C_3-7 cycloalkyl, or a heterocyclic group, and the C_1-6 alkyl, aryl, C_1-6 alkoxy, aryloxy, C_1-6 alkylamino, arylamino, C_1-6 alkylthio, arylthio, C_3-7 cycloalkyl, or heterocyclic group represented by R⁵ may be the same or different, and is optionally substituted by

(I) a halogen atom;

(II) C_1-6 alkyl optionally containing a substituent selected from the group consisting of (1) hydroxyl, (2) thiol, (3) amino, (4) C_1-6 alkoxy, (5) C_1-6 alkylthio, (6) C_1-6 alkylsulfinyl, (7) C_1-6 alkylsulfonyl, (8) mono- or di-C_1-6 alkylamino, (8′) amino substituted by a heterocyclic group optionally substituted by C_1-6 alkyl, (9) C_1-6 alkylcarbonyloxy, (10) C_1-6 alkylcarbonylthio, (11) C_1-6 alkylcarbonylamino, (12) aryloxy, (13) arylthio, (14) arylsulfinyl, (15) arylsulfonyl, (16) arylamino, (17) C_1-6 alkyl- or aryl-sulfonylamino, (18) C_1-6 alkyl- or aryl-ureido, (19) C_1-6 alkoxy- or aryloxy-carbonylamino, (20) C_1-6 alkylamino- or arylamino-carbonyloxy, (21) carboxyl, (22) nitro, (23) a heterocyclic group, (23′) Het-S(═O)j- wherein Het represents a heterocyclic group, j is 0, 1, or 2, and Het is optionally substituted by alkyl optionally substituted by mono- or di-C_1-6 alkylamino in which the di-C_1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms and one or two alkyl groups on the amino group and the cyclic amino moiety are optionally substituted by hydroxyl, (24) cyano, and (25) a halogen atom,

wherein the alkyl moiety in (4) the C_1-6 alkoxy group, (5) the C_1-6 alkylthio group, (6) the C_1-6 alkylsulfinyl group, and (7) the C_1-6 alkylsulfonyl group is optionally substituted by a halogen atom; C_1-6 alkyl; C_1-6 alkoxy; C_1-6 alkylthio; mono- or di-C_1-6 alkylamino in which the di-C_1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms; aryloxy; arylthio; hydroxyl; carboxyl; —S(═O)₂(—OH); C_1-6 alkoxy- or aryloxy-carbonyl; C_1-6 alkylcarbonyl; aryl; or a heterocyclic group optionally substituted by alkyl optionally substituted by mono- or di-C_1-6 alkylamino in which the di-C_1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms, and one or two alkyl groups on the amino group and the cyclic amino moiety are optionally substituted by hydroxy, and

in (8) the mono- or di-C_1-6 alkylamino group, the di-C_1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms, and one or two alkyl groups on the amino group and the cyclic amino moiety are optionally substituted by a halogen atom; C_1-6 alkyl optionally substituted by hydroxyl; C_1-6 alkoxy; C_1-6 alkylthio; mono- or di-C_1-6 alkylamino in which one or two alkyl groups on the amino group are optionally substituted by hydroxyl; arylamino in which the amino group is optionally substituted by C_1-6 alkyl; mono- or di-C_1-6 alkylcarbamoylmethyl in which the di-C_1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms, and one or two alkyl groups on the amino group and the cyclic amino moiety are optionally substituted by hydroxyl; aryloxy; arylthio; an oxygen atom; hydroxyl; carboxyl; C_1-6 alkoxy- or aryloxy-carbonyl; C_1-6 alkylcarbonyl; aryl optionally substituted by a halogen atom or hydroxyl; or a heterocyclic group;

(III) C_1-6 alkoxy optionally substituted by a halogen atom;

(IV) C_1-6 alkylthio optionally substituted by a halogen atom;

(V) C_3-7 cycloalkyl;

(VI) aryl;

(VII) aryloxy;

(VIII) C_1-6 alkylcarbonylamino;

(VIX) C_1-6 alkylcarbonyloxy;

(X) hydroxyl;

(XI) nitro;

(XII) cyano;

(XIII) amino;

(XIV) mono- or di-C_1-6 alkylamino in which the di-C_1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms;

(XV) arylamino;

(XVI) C_1-6 alkyl- or aryl-sulfonylamino;

(XVII) C_1-6 alkyl- or aryl-ureido;

(XVIII) C_1-6 alkoxy- or aryloxy-carbonylamino;

(XIX) C_1-6 alkylamino- or arylamino-carbonyloxy;

(XX) C_1-6 alkoxy- or aryloxy-carbonyl;

(XXI) acyl;

(XXII) carboxyl;

(XXIII) carbamoyl;

(XXIV) mono- or di-alkylcarbamoyl;

(XXV) a heterocyclic group;

(XXVI) alkyl- or aryl-sulfonyl;

(XXVII) C_2-6 alkenyloxy; or

(XXVIII) C_2-6 alkynyloxy,

Z represents group A or group B wherein R⁶, R⁷, and R¹⁷ are as defined in formula (I),

R¹⁰¹ and R¹⁰² together represent ═O, and R¹⁰³ and R¹⁰⁴ represent a hydrogen atom, or R¹⁰¹ and R¹⁰⁴ together represent a bond, and R¹⁰² and R¹⁰³ together represent a bond.

Compounds according to the present invention may form pharmaceutically acceptable salts thereof. Preferred examples of such salts include: alkali metal or alkaline earth metal salts such as sodium salts, potassium salts or calcium salts; hydrohalogenic acid salts such as hydrofluoride salts, hydrochloride salts, hydrobromide salts, or hydroiodide salts; inorganic acid salts such as nitric acid salts, perchloric acid salts, sulfuric acid salts, or phosphoric acid salts; lower alkylsulfonic acid salts such as methanesulfonic acid salts, trifluoromethanesulfonic acid salts, or ethanesulfonic acid salts; arylsulfonic acid salts such as benzenesulfonic acid salts or p-toluenesulfonic acid salts; organic acid salts such as fumaric acid salts, succinic acid salts, citric acid salts, tartaric acid salts, oxalic acid salts, maleic acid salts, acetic acid salts, malic acid salts, lactic acid salts, or ascorbic acid salts; and amino acid salts such as glycinate salts, phenylalanine salts, glutamic acid salts, or aspartic acid salts.

Production of Compounds

Compounds of formula (I) may be produced by reacting a hydrazine compound of formula (VI-1) or (VI-2) with a suitable carbonyl compound (compound C) in a suitable sovlent, for example, toluene, in the persence of a suitable acid catalyst, for example, acetic acid. wherein A, R⁵, R⁶, and R⁷ are as defined in formula (I).

The compound of formula (VI-1) and the compound of formula (VI-2) may be commercially available products, or alternatively may be produced by a production process which will be described later.

The compound of formula (VI-1) and the compound of formula (VI-2) may also be produced by reacting an amino compound of formula (VII) (compound A) with a suitable acid chloride (compound B), or by reacting an amino compound of formula (VII) (compound A) with a suitable carboxylic acid (compound B) in the presence of a suitable condensing agent, for example, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, to give an amide compound of formula (VIII), then adding hydrazine to the amide compound of formula (VIII) in a suitable solvent, for example, ethanol, and heating the mixture. A reduced form of formula (VI-2) can be produced by carrying out the hydrazination at a higher temperature and prolonging the reaction time. For example, the compound of formula (VI-1) can be produced under reaction conditions of 30 to 40° C. and 12 to 24 hr, while the compound of formula (VI-2) can be produced under reaction conditions of 110 to 120° C. and 72 to 96 hr. wherein A and R⁵ are as defined in formula (I); and R²¹ represents a hydrogen atom or a protective group of carboxyl.

The compound wherein R⁵ represents phenyl substituted by formula (IV) or formula (V) can be produced by reacting a compound of formula (VIIIa) with a compound of formula (IV′) or formula (V′) (compound B′) to give a compound of formula (VIIIb) and then subjecting the compound of formula (VIIIb) to reactions shown in scheme 1 and scheme 2. wherein A and R⁵ are as defined in formula (I); Q, X1, and R¹³ are as defined in formula (IV); X2, X3, R¹⁴ and R¹⁵ are as defined in formula (V); R²¹ represents a hydrogen atom or a protective group of carboxyl; Alk represents an alkylene chain having 1 to 6 carbon atoms; and Hal represents a halogen atom.

Tandem-type compounds of formula (I-3) can also be produced according to scheme 3. Specifically, a compound to which a compound of formula (VIIIa) has been bonded in a tandem manner can be produced by reacting the compound of formula (VIIIa) with H—NR²⁰⁵-T-NR^205′—H wherein R²⁰⁵, R^205′, and T are as defined in formula (I-3), instead of the compound of formula (IV′) and the compound of formula (V′). The compound of formula (I-3) can be produced by subjecting this compound to reactions shown in scheme 1 and scheme 2.

An imine reduced form of formula (I) in which Z represents —NH—CR⁶R⁷R¹⁷ can be produced by dissolving the compound produced according to scheme 1 in a suitable solvent, for example, methanol, and reducing the compound with a suitable reducing agent, for example, sodium borohydride). wherein A, R⁵, R⁶, R⁷ and R¹⁷ are as defined in formula (I).

Among amino compounds used as the starting compound in scheme 2, compounds in which ring A is a benzene ring can be synthesized by methods shown in schemes A to H. wherein R²¹ represents a hydrogen atom or a protective group of carboxyl; Alk represents an alkylene chain having 2 to 7 carbon atoms; n is an integer of 1 to 6; Hal represents a halogen atom, preferably a bromine or chlorine atom; R³⁰¹, R³⁰², R³⁰³, R³⁰⁴, and R³⁰⁵ represent optionally substituted C_1-6 alkyl, optionally substituted C_2-6 alkenyl, optionally substituted aryl, or the like; R¹, R², R³, and R⁴ are as defined in formula (I).

In the above schemes, the esterification can be carried out by esterifying a commercially available carboxylic acid with a suitable esterifying agent, for example, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride.

The introduction of the amino group can be carried out by allowing an alkylamino compound or an arylamino compound to act under basic condition, for example, potassium carbonate.

The reduction of the nitro group can be carried out using a suitable reducing agent, for example, palladium-carbon.

Use of Compounds

A group of sodium dependent phosphate transporters (NaPi) present in cells are known to be responsible for homeostasis of phosphorus in vivo. In particular, the phosphorus concentration of serum is generally regulated by phosphate absorption in intestinal epithelial cells and phosphate reabsorption in renal tubular cells, and the above phosphate transporters also participate in these mechanisms.

The compounds according to the present invention can inhibit these phosphate transporters that mainly specify phosphate absorption from the intestinal tract and phosphate reabsorption from the kidney (see Pharmacological Test Examples 1 to 3).

Further, the compounds according to the present invention can exhibit phosphate absorption inhibitory activity in the intestinal tract of rats (see Pharmacological Test Example 4).

Accordingly, the compounds according to the present invention can be used for the prevention or treatment of diseases for which serum phosphate lowering action is therapeutically effective.

The term “serum phosphate lowering action” as used herein means action that lowers phosphate concentration of serum. The phosphate concentration of serum is specified by (i) absorption from the intestinal tract and excretion into urine and feces and (ii) introduction and discharge with respect to cells in vivo and calcified tissue typified by osseous tissues. The “serum phosphate lowering action” as used herein embraces the action of lowering of the serum phosphate concentration in the case of action on a healthy living body and is not always limited to the action of lowering of serum phosphate concentration in hyperphosphatemia.

Further, the compounds according to the present invention can be used for the prevention or treatment of diseases for which phosphate transport inhibition is therapeutically effective.

The term “phosphate transport inhibition” as used herein means the inhibition of transport activity of phosphate transporters present on cell membranes of object cells. Object cells include epithelial cells of small intestine, renal epithelial cells, pulmonary epithelial cells, vascular endothelial cells, vascular smooth muscle cells, or osteoblasts.

Diseases for which the serum phosphate lowering action is effective therapeutically and diseases for which phosphate transport inhibition is therapeutically effective include (1) hyperphosphatemia, (2) renal failure and chronic renal failure, (3) secondary hyperparathyroidism and diseases related thereto, (4) metabolic osteopathy, (5) diseases for which the suppression of calcium and/or phosphorus product is effective therapeutically, and (6) other hyperphosphatemia-related diseases.

(1) Hyperphosphatemia

The compounds according to the present invention can lower the phosphate concentration of serum and can inhibit phosphate transport and thus can be used for the prevention or treatment of hyperphosphatemia. The term “hyperphosphatemia” as used herein means such a state that the phosphate concentration of serum is beyond a clinically defined normal region.

(2) Renal Failure and Chronic Renal Failure

Regarding renal failure and chronic renal failure, it has recently been suggested that an increase in serum phosphate concentration per se is an exacerbation factor of renal failure. In fact, there are a series of reports on that the progress of the renal failure can be delayed by restriction of phosphate ingestion in chronic renal failure patients (Maschio et al., Kidney Int., 22:371-376, 1982, Maschio et al., Kidney Int., 24:S273-277, 1983, Barsotti et al., Kidney Int. 24:S278-284, 1983).

Accordingly, the compounds according to the present invention which can inhibit phosphate transport and can lower phosphate concentration of serum can be used for the prevention or treatment of the renal failure and the chronic renal failure.

(3) Secondary Hyperparathyroidism and Primary Hyperparathyroidism and Diseases Related Thereto

It is known that hyperphosphatemia secondarily leads to hypocalcemia and thus induces secondary hyperparathyroidism. Accordingly, the compounds according to the present invention can be used for the prevention and treatment of secondary hyperparathyroidism.

Further, in recent years, there are a report that a rise of phosphate concentration promotes the secretion of PTH (parathyroid hormone) from parathyroid cells (Almanden Y et al., J Bone Miner Res 11:970-976, 1996), a report that phosphorus restriction suppresses the secretion (Rachel K et al., J Clin Invest 96.327-333, 1995), a report that hyperplasia of parathyroids is suppressed (Slatopolsky E et al., J Clin Invest 97:2534-2540, 1996) and the like. When these reports suggesting that the serum phosphate concentration per se participates in hyperplasia of parathyroids and PTH secretion are taken into consideration, it can be said that the compounds according to the present invention can be used for the prevention and treatment of secondary hyperparathyroidism as well as primary hyperparathyroidism through a lowering in serum phosphate concentration. Further, the compounds according to the present invention can be used for the prevention and treatment of renal osteodystrophy induced by secondary hyperparathyroidism, that is, osteitis fibrosa, ostealgia and arthralgia, bone deformity, fracture and the like.

The compounds according to the present invention can prevent and treat secondary hyperparathyroidism and thus can also be used for the prevention and treatment of diseases said to be induced by PTH increase in the secondary hyperparathyroidism, for example, central or peripheral nervous system damage, anemia, myocardiopathy, hyperlipidemia, anomaly of saccharometabolism, pruritus cutaneus, tendon rupture, sexual dysfunction, muscle damage, skin ischemic ulcer, growth retardation, heart conduction disturbance, pulmonary diffusing impairment, immune deficiency, ostealgia and arthralgia, bone deformity, or fracture.

(4) Calcium and Phosphorus Metabolic Disorder

The compounds according to the present invention can remedy clinical conditions of phosphorus metabolic disorder and, at the same time, are considered to have the effect of remedying clinical conditions of metabolic disorder of minerals including calcium. Accordingly, the compounds according to the present invention can be used for the prevention and treatment of calcium and phosphorus metabolic disorders such as metabolic osteopathy.

(5) Diseases for Which Suppression of Calcium and/or Phosphorus Product is Therapeutically Effective

In dialysis patients, when poor control of serum phosphate concentration due to administration of a large amount of calcium preparations and administration of a large amount of vitamin D, and overconsumption of proteins is likely to cause ectopic calcification as a result of a rise of calcium and phosphorus product in blood and is in its turn causative of circulatory disorders derived from calcification of blood circulatory systems including coronary artery (Braun J et al., Am J Kidney Dis. 27:394-401, 1996, Goodman W G et al., N Engl J Med 342:1478-1483, 2000, Kimura K et al., Kidney Int. 71: S238-241, 1999). In this case, downward revision of calcium and phosphorus product is effective in remedying clinical condition (Geoffrey A B et al., Am J Kidney Dis. 31:607-617, 1998). The compounds according to the present invention are hyperphosphatemia improving drugs different from calcium preparations and thus can lower the phosphate concentration of serum without a rise of calcium concentration of serum. Thus, the compounds according to the present invention can be used for the treatment of diseases for which the suppression of calcium and/or phosphorus product in blood vessels is therapeutically effective. Such diseases include calcification of cardiovascular system in dialysis patients, age-related arterial sclerosis, diabetic vasculopathy, calcification of soft tissue, metastatic calcification, and ectopic calcification. Since a rise of calcium and phosphorus product is recognized as a risk factor of clinical conditions of red eye, arthralgia, myalgia, pruritus cutaneus, heart conduction disturbance, pulmonary diffusing impairment, angina pectoris, cardiac infarction, or heart failure induced by cardiac murmur or valvular disease (Tetsuo Tagami, Jin To Toseki (Kidney and Dialysis), Vol. 49:189-191, 2000), the compounds according to the present invention can also be used for the prevention and treatment of these diseases.

(6) Other Diseases Related to Hyperphosphatemia

In addition to the above diseases (1) to (5), hypoparathyroidism, pseudohypoparathyroidism, hypocalcemia, hypercalciuria, vitamin D toxicosis, acromegaly, overdose of phosphate, acidosis, state of hypercatabolism, rhabdomyolysis, hemolytic anemia, climacteric disturbance, malignant tumor, tumor lysis syndrome, and tumoral calcinosis involve hyperphosphatemia. Therefore, the compounds according to the present invention can also be used for the prevention and treatment of these diseases.

According to the present invention, there is provided a serum phosphate concentration lowering agent comprising the compound according to the present invention.

According to the present invention, there is provided a phosphate transport inhibitor comprising the compound according to the present invention.

According to the present invention, there is provided a method for lowering serum phosphate concentration, comprising administering the compound according to the present invention to a human or a mammal other than a human.

According to the present invention, there is provided a method for inhibiting phosphate transport, comprising administering the compound according to the present invention to a human or mammal other than a human.

Pharmaceutical Preparation

The compounds according to the present invention can be administered to human and non-human animals orally or parenterally by administration routes, for example, intraoral, nasal administration, transpulmonary administration, intrarectal administration, percutaneous administration, subcutaneous administration, or intravenous administration. Therefore, the compounds according to the present invention can be formulated into suitable dosage forms according to the administration routes. Dosage forms suitable for the above administration routes include tablets, capsules, granules, powders, ointments, poultices, aerosols, suppositories, and injections.

The compound according to the present invention per se can be administered to patients, or alternatively may be administered together with general-purpose preparation additives to patients.

The pharmaceutical composition according to the present invention can be produced according to a well-known formulation technique by using the compound according to the present invention together with the following additives.

For example, oral preparations, that is, tablets, capsules, granules, and powders, can be produced by conventional methods with the compounds according to the present invention and suitable preparation additives. Additives usable for oral preparations include excipients, binders, disintegrants, and lubricants. They may be used either solely or in a combination of two or more. Excipients include, for example, lactose, mannitol, corn starch, and calcium carbonate. Binders include, for example, gum arabic, tragacanth, gelatin, and methylcellulose. Disintegrants include, for example, corn starch, crystalline cellulose, and carboxymethylcellulose sodium. Lubricants include, for example, talc, and magnesium stearate.

Oral preparations containing the compound according to the present invention may be coated with a coating agent according to a well known method. Coating agents usable herein include, for example, hydroxypropylcellulose, hydroxypropylmethylcellulose, aminoalkylmethacrylate copolymer, hydroxypropylmethylcellulose phthalate, and carboxymethylethylcellulose.

Oral preparations can be modified for effectively drawing phosphate absorption inhibition from intestinal tracts of the compound according to the present invention.

When the compounds according to the present invention are orally administered, there is a possibility that, after the inhibition of phosphate transport carriers in small intestine epithelial cells, they are absorbed in the body and inhibit phosphate transport carriers in vascular endothelial cells, pulmonary epithelial cells, renal epithelial cells, osteoblasts and the like. Accordingly, the compounds according to the present invention have the possibility of inhibiting phosphate absorption from the intestine and further inhibiting phosphate absorption in the kidney to synergistically and effectively lower the phosphate concentration of serum. However, the possibility of exhibiting unknown toxicity upon absorption of the compounds according to the present invention in the body cannot be denied. To avoid this phenomenon, a technique may be adopted in which the compounds according to the present invention can specifically inhibit only small intestine epithelium, which is the first barrier for phosphate absorption from outside of the body, without the absorption from the intestinal tract. For example, the absorption of the compound per se from the intestinal tract can be prevented by bonding an inert water-soluble polymer to the compounds according to the present invention to increase the water solubility and molecular weight. Water soluble polymers usable herein include, for example, polyethylene glycol, dextran, and gelatin.

An enteric coating may be applied to the oral preparation according to the present invention for specific dissolution in the intestinal tract after oral administration. The enteric coating may be carried out by a well-known method using an enteric coating agent. Enteric coating agents include, for example, hydroxypropylmethylcellulose phthalate, hydroxypropylmethylcellulose acetate succinate, carboxymethylethylcellulose, and methacrylic acid copolymers.

Further, any foamable substance, which, after oral administration, can promote dissolution speed of the preparation in the intestinal tract to enhance the concentration of the effective ingredient, can be added to the oral preparation according to the present invention. Substances which are foamable upon dissolution include, for example, a combination of sodium hydrogencarbonate and citric acid.

Further, any substance, which, after oral administration, can improve the residence of the preparation in the intestinal tract, can be added to the oral preparation according to the present invention. Substances which can improve the residence include substances which become viscous upon dissolution, and examples thereof include sodium alginate, carboxymethylcellulose sodium, hydroxyethylcellulose, hydroxypropylcellulose, hydroxypropylmethylcellulose, polyvinyl alcohol, polyvintyl pyrrolidone, carboxylvinyl polymer, and chitosan.

In the oral preparation according to the present invention, the above modification methods may be properly used in combination.

The compounds according to the present invention and suitable preparation additives may be used for the manufacture of injections by a general-purpose method. Additives usable in injections include diluents, pH adjustors, tonicity adjusting agents, dissolution aids, and preservatives. They may be used either solely or in a combination of two or more. Diluents include, for example, distilled water for injections. pH adjustors include, for example, hydrochloric acid, sodium hydroxide, a combination of acetic acid with sodium acetate, and a combination of disodium hydrogenphosphate with sodium dihydrogenphosphate. Tonicity adjusting agents include, for example, sodium chloride, glucose, mannitol, and glycine. Dissolution aids include, for example, ethanol, Polysorbate 20, Polysorbate 80, sucrose fatty acid ester, and propylene glycol. Preservatives include, for example, chlorobutanol, benzalconium chloride, and benzethonium chloride.

For the compounds according to the present invention, the dose may be appropriately determined in consideration of particular conditions, for example, the age, weight, sex, type of disease, and severity of condition of patients, and the preparation may be administered, for example, in an amount of 0.1 to 1000 mg/kg, preferably 0.5 to 100 mg/kg, more preferably 1 to 20 mg/kg. This dose may be administered at a time daily or divided doses of several times daily.

EXAMPLES

The present invention is further illustrated by the following Examples that are not intended as a limitation of the scope of the invention.

Example 1

Compound 1 3,4-Dimethoxy-N-[2-(3-phenyl-allylidene-hydrazinocarbonyl)-phenyl]-benzamide

Methyl 2-aminobenzoate (compound A) (2.0 g) was dissolved in anhydrous methylene chloride (40.0 ml). Subsequently, pyridine (2.0 ml) and 3,4-dimethoxybenzoyl chloride (compound B) (3.14 g) were added to the solution at room temperature, and the mixture was stirred at that temperature for 30 min. After the completion of the reaction, distilled water was added thereto, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with a saturated aqueous sodium chloride solution, was dried over sodium sulfate, and was then concentrated to give methyl 2-[(3,4-dimethoxybenzoyl)amino]benzoate as a useful intermediate (4.17 g, yield 100%).

Methyl 2-[(3,4-dimethoxybenzoyl)amino]benzoate (4.17 g) produced by the above reaction was dissolved in ethanol (40.0 ml). Hydrazine monohydrate (20.0 ml) was added at room temperature, and the mixture was stirred with heating under reflux for 12 hr. After the completion of the reaction, the reaction solution was allowed to cool at room temperature and was cooled under ice cooling to precipitate crystals. The precipitated crystals were collected by filtration through Kiriyama Rohto (40 mmφ) and were washed with ether to give N-(2-hydrazinocarbonyl-phenyl)-3,4-dimethoxybenzamide as a hydrazine compound (3.55 g, yield 91.3%).

N-(2-Hydrazinocarbonyl-phenyl)-3,4-dimethoxybenzamide (50.0 mg) was dissolved in anhydrous toluene (1.0 ml). Subsequently, a catalytic amount of acetic acid and trans-cinnamaldehyde (compound C) (40.0 μl) were added at room temperature, and the mixture was stirred with heating under reflux for 30 min. After the completion of the reaction, the reaction solution was allowed to cool at room temperature and was cooled under ice cooling to precipitate crystals. The precipitated crystals were filtered through Kiriyama Rohto (21 mmφ) and were washed with toluene and hexane. The crystals were dried through a vacuum pump to give the title compound 1 (39.0 mg, yield 57.0%).

Mass spectrometric value (ESI-MS) 428 (M−1)

Compound 2 N-[2-(2-Fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 2 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 420 (M−1)

Compound 3 3,4-Dimethoxy-N-[2-(2-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 3 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 416 (M−1)

Compound 4 3,4-Dimethoxy-N-[2-(2-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 4 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 432 (M−1)

Compound 5 3,4-Dimethoxy-N-[2-(3-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 5 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 432 (M−1)

Compound 6 N-[2-(3,5-Di-tert-butyl-4-hydroxy-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 6 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 530 (M−1)

Compound 7 3,4-Dimethoxy-N-[2-(2-methyl-3-phenyl-allylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 7 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 442 (M−1)

Compound 8 N-[2-(3,5-Bis-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 8 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 538 (M−1)

Compound 9 N-[2-(3-Cyano-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 9 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 427 (M−1)

Compound 10 N-[2-(2-Bromo-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 10 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 480 (M−1)

Compound 11 N-[2-(4-Hydroxy-3-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 11 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 448 (M−1)

Compound 12 3,4-Dimethoxy-N-[2-(3,4,5-trimethoxy-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 12 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 492 (M−1)

Compound 13 N-[4-Bromo-2-(3-phenyl-allylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 13 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 508 (M−1)

Compound 14 N-[4-Bromo-2-(2-bromo-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 14 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 560 (M−1)

Compound 15 N-[2-(3-Fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 15 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 420 (M−1)

Compound 16 N-[2-(4-Fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 16 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 420 (M−1)

Compound 17 N-[2-(Benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 17 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 402 (M−1)

Compound 18 N-[2-(3-Hydroxy-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 18 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 418 (M−1)

Compound 19 N-[2-(4-Hydroxy-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 19 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 418 (M−1)

Compound 20 3,4-Dimethoxy-N-[2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 20 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 416 (M−1)

Compound 21 N-[2-(Furan-2-ylmethylene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 21 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 392 (M−1)

Compound 22 3,4-Dimethoxy-N-[2-(5-methyl-furan-2-ylmethylene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 22 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 406 (M−1)

Compound 23 3,4-Dimethoxy-N-[2-(thiophen-2-ylmethylene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 23 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 408 (M−1)

Compound 24 3,4-Dimethoxy-N-[2-(thiophen-3-ylmetylene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 24 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 408 (M−1)

Compound 25 N-[2-(2,4-Dihydroxy-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 25 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 434 (M−1)

Compound 26 N-[2-(3,4-Dihydroxy-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 26 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 434 (M−1)

Compound 27 N-[2-(Benzylidene-hydrazinocarbonyl)-phenyl]-2-fluoro-benzamide

The title compound 27 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 360 (M−1)

Compound 28 N-[4-Bromo-2-(2-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 28 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 500 (M−1)

Compound 29 N-[4-Bromo-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 29 was produced in the same manner as in Example 1.

¹H-NMR (CDCl₃, 400 MHz): δ 8.55 (1H, d, J=9.0 Hz), 8.32 (1H, bs), 7.49-7.67 (6H, m), 7.40 (1H, q, J=4.56 Hz), 7.13 (1H, q, J=5.53 Hz), 6.93 (1H, d, J=8.8 Hz), 3.98 (3H, s), 3.94 (3H, s)

Mass spectrometric value (ESI-MS) 500 (M−1)

Compound 30 N-[4-Bromo-2-(2-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 30 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 494 (M−1)

Compound 31 N-[4-Bromo-2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 31 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 494 (M−1)

Compound 32 N-[2-(3-Chloro-4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 32 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 454 (M−1)

Compound 33 3,4-Dimethoxy-N-[2-(4-trifluoromethoxy-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 33 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 486 (M−1)

Compound 34 N-[2-(3-Bromo-4-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 34 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 512 (M−1)

Compound 35 N-[2-(3-Chloro-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 35 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 436 (M−1)

Compound 36 N-[2-(4-Hydroxy-3,5-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 36 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 446 (M−1)

Compound 37 N-[2-(3-Ethoxy-4-hydroxy-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 37 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 462 (M−1)

Compound 38 2-Fluoro-N-[2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 38 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 378 (M−1)

Compound 39 2-Fluoro-N-[2-(3-hydroxy-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 39 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 376 (M−1)

Compound 40 2-Fluoro-N-[2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 40 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 374 (M−1)

Compound 41 N-[2-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 41 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 504 (M−1)

Compound 42 N-[2-(4-Hydroxy-3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 42 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 432 (M−1)

Compound 43 N-[2-(2,5-Dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 43 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 430 (M−1)

Compound 44 N-[2-(2-Fluoro-5-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 44 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 488 (M−1)

Compound 45 2-Fluoro-N-[2-(4-hydroxy-3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 45 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 390 (M−1)

Compound 46 N-[2-(2,5-Dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-2-fluoro-benzamide

The title compound 46 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 388 (M−1)

Compound 47 N-[2-(3-Fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-4-methoxy-benzamide

The title compound 47 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 390 (M−1)

Compound 48 N-[2-(4-Fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-4-methoxy-benzamide

The title compound 48 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 390 (M−1)

Compound 49 4-Methoxy-N-[2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 49 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 386 (M−1)

Compound 50 N-[2-(3-Hydroxy-benzylidene-hydrazinocarbonyl)-phenyl]-4-methoxy-benzamide

The title compound 50 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 388 (M−1)

Compound 51 4-Methoxy-N-[2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 51 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 386 (M−1)

Compound 52 N-[2-(4-Allyloxy-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 52 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 458 (M−1)

Compound 53 N-[2-(3,5-Dimethoxy-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 53 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 462 (M−1)

Compound 54 3,4-Dimethoxy-N-{2-[3-(3-trifluoromethyl-phenoxy)-benzylidene-hydrazinocarbonyl]-phenyl}-benzamide

The title compound 54 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 562 (M−1)

Compound 55 N-[2-(3-Fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-3,5-dimethoxy-benzamide

The title compound 55 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 420 (M−1)

Compound 56 N-[2-(4-Fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-3,5-dimethoxy-benzamide

The title compound 56 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 420 (M−1)

Compound 57 3,5-Dimethoxy-N-[2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 57 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 416 (M−1)

Compound 58 N-[2-(3-Hydroxy-benzylidene-hydrazinocarbonyl)-phenyl]-3,5-dimethoxy-benzamide

The title compound 58 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 418 (M−1)

Compound 59 N-[4-Bromo-2-(3-chloro-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 59 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 516 (M−1)

Compound 60 N-[4-Bromo-2-(4-chloro-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 60 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 516 (M−1)

Compound 61 N-[4-Bromo-2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 61 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 500 (M−1)

Compound 62 N-[4-Bromo-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 62 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 494 (M−1)

Compound 63 N-[4-Bromo-2-(3-hydroxy-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 63 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 496 (M−1)

Compound 64 N-[4-Bromo-2-(4-hydroxy-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 64 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 496 (M−1)

Compound 65 N-[4-Chloro-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 65 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 454 (M−1)

Compound 66 N-[4-Chloro-2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 66 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 454 (M−1)

Compound 67 N-[4-Chloro-2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 67 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 450 (M−1)

Compound 68 N-[4-Chloro-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 68 was produced in the same manner as in Example 1.

¹H-NMR (CDCl₃, 400 MHz): δ 9.33 (1H, s), 8.72 (1H, d, J=8.76 Hz), 8.21 (1H, s), 7.48-7.68 (6H, m), 7.20-7.25 (1H, m), 6.92 (1H, d, J=8.56 Hz), 3.97 (3H, s), 3.93 (3H, s), 2.38 (3H, s)

Mass spectrometric value (ESI-MS) 450 (M−1)

Compound 69 N-[4-Chloro-2-(3-hydroxy-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 69 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 452 (M−1)

Compound 70 N-[4-Chloro-2-(4-hydroxy-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 70 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 452 (M−1)

Compound 71 N-[5-Chloro-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 71 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 454 (M−1)

Compound 72 N-[5-Chloro-2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 72 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 454 (M−1)

Compound 73 N-[5-Chloro-2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 73 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 450 (M−1)

Compound 74 N-[5-Chloro-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 74 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 452 (M−1)

Compound 75 N-[5-Chloro-2-(3-hydroxy-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 75 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 452 (M−1)

Compound 76 4-Fluoro-N-[2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 76 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 379 (M−1), 757 (2M−1)

Compound 77 4-Fluoro-N-[2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 77 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 378 (M−1)

Compound 78 4-Fluoro-N-[2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 78 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 374 (M−1)

Compound 79 4-Fluoro-N-[2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 79 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 374 (M−1)

Compound 80 4-Fluoro-N-[2-(3-hydroxy-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 80 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 376 (M−1)

Compound 81 3-Fluoro-N-[2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 81 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 378 (M−1)

Compound 82 3-Fluoro-N-[2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 82 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 757 (2M−1)

Compound 83 3-Fluoro-N-[2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 83 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 374 (M−1)

Compound 84 3-Fluoro-N-[2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 84 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 374 (M−1)

Compound 85 3-Fluoro-N-[2-(3-hydroxy-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 85 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 376 (M−1)

Compound 86 3-Fluoro-N-[2-(4-hydroxy-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 86 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 376 (M−1)

Compound 87 N-[4-Bromo-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 87 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 582, 584 (M−1)

Compound 88 N-[4-Chloro-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 88 was produced in the same manner as in Example 1.

¹H-NMR (CDCl₃, 400 MHz): δ 8.49 (1H, d, J=8.08 Hz), 8.39 (1H, s), 8.06 (1H, s), 7.96 (1H, s), 7.49-7.60 (4H, m), 7.41 (1H, d, J=9.04 Hz), 6.94 (1H, d, J=8.56 Hz), 3.98 (3H, s,), 3.94 (3H, s)

Mass spectrometric value (ESI-MS) 538, 540 (M−1)

Compound 89 N-[2-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-3,5-dimethoxy-benzamide

The title compound 89 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 504, 506 (M−1)

Compound 90 N-[2-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-methoxy-benzamide

The title compound 90 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 474 (M−1)

Compound 91 N-[4-Bromo-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 91 was produced in the same manner as in Example 1.

¹H-NMR (CDCl₃, 400 MHz): δ 9.53 (1H, s), 8.61 (1H, d, J=9.04 Hz), 8.21 (1H, s), 7.69 (1H, s), 7.59-7.62 (4H, m), 7.46-7.50 (1H, m), 7.17 (1H, d, J=7.56 Hz), 6.91 (1H, d, J=8.28 Hz), 3.97 (3H, s), 3.93 (3H, s), 2.28 (3H, s), 2.28 (3H, s)

Mass spectrometric value (ESI-MS) 508 (M−1)

Compound 92 N-[4-Chloro-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 92 was produced in the same manner as in Example 1.

¹H-NMR (CDCl₃, 400 MHz): δ 9.60 (1H, s), 8.65 (1H, d, J=9.04 Hz), 8.21 (1H, s), 7.44-7.62 (6H, m), 7.17 (1H, d, J=7.80 Hz), 6.91 (1H, d, J=8.32 Hz), 3.97 (3H, s), 3.92 (3H, s), 2.28 (6H, s)

Mass spectrometric value (ESI-MS) 464 (M−1)

Compound 93 N-[2-(3,4-Dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-3,5-dimethoxy-benzamide

The title compound 93 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 430 (M−1)

Compound 94 N-[2-(3,4-Dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-methoxy-benzamide

The title compound 94 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 400 (M−1)

Compound 95 N-[2-(3,4-Dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-fluoro-benzamide

The title compound 95 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 388 (M−1)

Compound 96 N-[2-(3,4-Dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-fluoro-benzamide

The title compound 96 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 388 (M−1)

Compound 97 N-[4-Bromo-2-(3-bromo-4-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 97 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 590 (M−1)

Compound 98 N-[2-(3-Bromo-4-methoxy-benzylidene-hydrazinocarbonyl)-4-chloro-phenyl]-3,4-dimethoxy-benzamide

The title compound 98 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 544 (M−1)

Compound 99 N-[2-(3-Bromo-4-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-3,5-dimethoxy-benzamide

The title compound 99 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 510 (M−1)

Compound 100 N-[2-(3-Bromo-4-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-4-methoxy-benzamide

The title compound 100 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 482 (M−1)

Compound 101 N-[2-(3-Bromo-4-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-3-fluoro-benzamide

The title compound 101 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 468, 470 (M−1)

Compound 102 N-[2-(3-Bromo-4-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-4-fluoro-benzamide

The title compound 102 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 468, 470 (M−1)

Compound 103 3,4-Dimethoxy-N-[2-(3-nitro-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 103 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 447 (M−1)

Compound 104 N-[2-(4-Dimethylamino-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 104 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 445 (M−1)

Compound 105 N-[4-Bromo-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-4-fluoro-benzamide

The title compound 105 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 458 (M−1)

Compound 106 N-[4-Bromo-2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-4-fluoro-benzamide

The title compound 106 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 456 (M−1)

Compound 107 N-[4-Bromo-2-(3-chloro-benzylidene-hydrazinocarbonyl)-phenyl]-4-fluoro-benzamide

The title compound 107 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 472, 474 (M−1)

Compound 108 N-[4-Bromo-2-(4-chloro-benzylidene-hydrazinocarbonyl)-phenyl]-4-fluoro-benzamide

The title compound 108 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 472, 474 (M−1)

Compound 109 N-[4-Bromo-2-(3-hydroxy-benzylidene-hydrazinocarbonyl)-phenyl]-4-fluoro-benzamide

The title compound 109 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 456, 458 (M−1)

Compound 110 N-[4-Bromo-2-(pyridin-3-ylmethylene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 110 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 483 (M−1)

Compound 111 N-[4-Chloro-2-(pyridin-3-ylmethylene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 111 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 437 (M−1)

Compound 112 4-Methoxy-N-[2-(pyridin-3-ylmethylene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 112 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 373 (M−1)

Compound 113 4-Fluoro-N-[2-(pyridin-3-ylmethylene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 113 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 361 (M−1)

Compound 114 N-[4-Bromo-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-3,5-dimethoxy-benzamide

The title compound 114 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 498 (M−1)

Compound 115 N-[4-Bromo-2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-3,5-dimethoxy-benzamide

The title compound 115 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 498, 500 (M−1)

Compound 116 N-[4-Bromo-2-(3-chloro-benzylidene-hydrazinocarbonyl)-phenyl]-3,5-dimethoxy-benzamide

The title compound 116 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 516, 518 (M−1)

Compound 117 N-[4-Bromo-2-(4-chloro-benzylidene-hydrazinocarbonyl)-phenyl]-3,5-dimethoxy-benzamide

The title compound 117 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 514, 516 (M−1)

Compound 118 N-[4-Bromo-2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-3,5-dimethoxy-benzamide

The title compound 118 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 496 (M−1)

Compound 119 N-[4-Bromo-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-3,5-dimethoxy-benzamide

The title compound 119 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 494 (M−1)

Compound 120 N-[2-(3-Fluoro-benzylidene-)-hydrazinocarbonyl)-phenyl)-3-trifluoromethoxy-benzamide

The title compound 120 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 444 (M−1)

Compound 121 N-[2-(4-Fluoro-benzylidene-)-hydrazinocarbonyl)-phenyl)-3-trifluoromethoxy-benzamide

The title compound 121 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 444 (M−1)

Compound 122 N-[2-(3-Chloro-benzylidene-)-hydrazinocarbonyl)-phenyl)-3-trifluoromethoxy-benzamide

The title compound 122 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 459, 461 (M−1)

Compound 123 N-[2-(4-Chloro-benzylidene-)-hydrazinocarbonyl)-phenyl)-3-trifluoromethoxy-benzamide

The title compound 123 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 459, 461 (M−1)

Compound 124 N-[2-(4-Methyl-benzylidene-)-hydrazinocarbonyl)-phenyl)-3-trifluoromethoxy-benzamide

The title compound 124 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 440 (M−1)

Compound 125 N-[4-(3-Dimethylamino-propoxy)-2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 125 was produced in the same manner as in Example 2, except that N-(2-chloroethyl)-N,N-dimethylamine hydrochloride was changed to 3-dimethylaminopropyl chloride hydrochloride.

Mass spectrometric value (ESI-MS) 521, 523 (M−1)

Compound 126 N-[4-Chloro-2-(3,4-dimethoxy-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 126 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 496 (M−1)

Compound 127 N-[4-Bromo-2-(3,4-dimethoxy-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 127 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 540 (M−1)

Compound 128 N-[4-Bromo-2-(3,4-dimethoxy-benzylidene-hydrazinocarbonyl)-phenyl]-3,5-dimethoxy-benzamide

The title compound 128 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 542 (M−1)

Compound 129 N-[2-(3-Fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-nicotinamide

The title compound 129 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 361 (M−1)

Compound 130 N-[2-(4-Fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-nicotinamide

The title compound 130 was produced in the same manner as in Example 1.

¹H-NMR (CDCl₃, 400 MHz): δ 9.69 (1H, s), 9.28 (1H, s), 8.77 (1H, dd, J=1.44 Hz, J=4.88 Hz), 8.66 (1H, d, J=7.80 Hz), 8.25-8.33 (2H, m), 7.81 (2H, s), 7.50-7.60 (2H, m), 7.43 (1H, dd, J=4.88 Hz, J=8.04 Hz), 7.05-7.15 (3H, m)

Mass spectrometric value (ESI-MS) 361 (M−1)

Compound 131 N-[2-(3-Methyl-benzylidene-hydrazinocarbonyl)-phenyl]-nicotinamide

The title compound 131 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 357 (M−1)

Compound 132 N-[2-(4-Methyl-benzylidene-hydrazinocarbonyl)-phenyl]-nicotinamide

The title compound 132 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 357 (M−1)

Compound 133 N-[2-(3,4-Dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-nicotinamide

The title compound 133 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 371 (M−1)

Compound 134 N-[2-(3-Fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-isonicotinamide

The title compound 134 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 361 (M−1)

Compound 135 N-[2-(4-Fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-isonicotinamide

The title compound 135 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 361 (M−1)

Compound 136 N-[2-(3-Methyl-benzylidene-hydrazinocarbonyl)-phenyl]-isonicotinamide

The title compound 136 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 357 (M−1)

Compound 137 N-[2-(4-Methyl-benzylidene-hydrazinocarbonyl)-phenyl]-isonicotinamide

The title compound 137 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 357 (M−1)

Compound 138 N-[2-(3,4-Dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-isonicotinamide

The title compound 138 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 371 (M−1)

Example 2

Compound 139 N-[4-(2-Dimethylamino-ethoxy-)-2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

N-[2-(4-Fluoro-benzylidene-hydrazinocarbonyl)-4-hydroxy-phenyl]-3,4-dimethoxy-benzamide (50 mg) synthesized in the same manner as in Example 1 was dissolved in anhydrous DMF (1.5 ml). NaH (60% in oil, 20 mg) was added to the solution at room temperature, and the mixture was stirred at that temperature for 5 min. Subsequently, N-(2-chloroethyl)-N,N-dimethylamine hydrochloride (47 mg) was added to the reaction solution at room temperature, and the mixture was stirred at that temperature for 12 hr. After the completion of the reaction, distilled water was added dropwise thereto under ice cooling and the mixture was subjected to separatory extraction with ethyl acetate. The organic layer was washed with saturated brine and was dried over sodium sulfate, and the organic layer was concentrated under the reduced pressure. The residue was purified by preparative TLC to give the title compound 139 (32 mg, yield 57.1%).

Mass spectrometric value (ESI-MS) 507 (M−1)

Compound 140 N-[4-(2-Diethylamino-ethoxy)-2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 140 was produced in the same manner as in Example 2, except that N-(2-chloroethyl)-N,N-dimethylamine hydrochloride was changed to 2-diethylaminoethyl chloride hydrochloride.

Mass spectrometric value (ESI-MS) 535 (M−1)

Compound 141 N-[2-(3-Fluoro-benzylidene-hydrazinocarbonyl)-4-methoxy-phenyl]-3,4-dimethoxy-benzamide

The title compound 141 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 450 (M−1)

Compound 142 N-[2-(4-Fluoro-benzylidene-hydrazinocarbonyl)-4-methoxy-phenyl]-3,4-dimethoxy-benzamide

The title compound 142 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 450 (M−1)

Compound 143 3,4-Dimethoxy-N-[4-methoxy-2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 143 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 446 (M−1)

Compound 144 3,4-Dimethoxy-N-[4-methoxy-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 144 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 446 (M−1)

Compound 145 N-[2-(3,4-Dimethyl-benzylidene-hydrazinocarbonyl)-4-methoxy-phenyl]-3,4-dimethoxy-benzamide

The title compound 145 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 460 (M−1)

Compound 146 N-[2-(3-Fluoro-benzylidene-hydrazinocarbonyl)-4-methyl-phenyl]-3,4-dimethoxy-benzamide

The title compound 146 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 434 (M−1)

Compound 147 N-[2-(4-Fluoro-benzylidene-hydrazinocarbonyl)-4-methyl-phenyl]-3,4-dimethoxy-benzamide

The title compound 147 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 434 (M−1)

Compound 148 3,4-Dimethoxy-N-[4-methyl-2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 148 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 430 (M−1)

Compound 149 3,4-Dimethoxy-N-[4-methyl-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 149 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 430 (M−1)

Compound 150 N-[2-(3,4-Dimethyl-benzylidene-hydrazinocarbonyl)-4-methyl-phenyl]-3,4-dimethoxy-benzamide

The title compound 150 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 444 (M−1)

Compound 151 Furan-2-carboxylic acid [4-bromo-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-amide

The title compound 151 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 428 (M−1)

Compound 152 Furan-2-carboxylic acid [4-bromo-2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-amide

The title compound 152 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 428 (M−1)

Compound 153 Furan-2-carboxylic acid [4-bromo-2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-amide

The title compound 153 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 426 (M−1)

Compound 154 Furan-2-carboxylic acid [4-bromo-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-amide

The title compound 154 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 424 (M−1)

Compound 155 Furan-2-carboxylic acid [4-bromo-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-amide

The title compound 155 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 438 (M−1)

Compound 156 Furan-2-carboxylic acid [4-bromo-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-amide

The title compound 156 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 513, 514 (M−1)

Compound 157 Thiophene-2-carboxylic acid [4-bromo-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-amide

The title compound 157 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 446 (M−1)

Compound 158 Thiophene-2-carboxylic acid [4-bromo-2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-amide

The title compound 158 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 446 (M−1)

Compound 159 Thiophene-2-carboxylic acid [4-bromo-2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-amide

The title compound 159 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 440 (M−1)

Compound 160 Thiophene-2-carboxylic acid [4-bromo-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-amide

The title compound 160 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 440 (M−1)

Compound 161 Thiophene-2-carboxylic acid [4-bromo-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-amide

The title compound 161 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 454, 456 (M−1)

Compound 162 Thiophene-2-carboxylic acid [4-bromo-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-amide

The title compound 162 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 530 (M−1)

Example 3

Compound 163 N-[2-(3,4-Dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-isonicotinamide hydrochloride

A 10% hydrochloric acid-methanol solution (1.0 ml) was added to compound 138 (50 mg) synthesized in the same manner as in Example 1 at room temperature. Further, diethyl ether (5.0 ml) was added thereto, and the mixture was stirred for 30 sec. The reaction solution as such was filtered through Kiriyama Rohto (21 mmφ), and the crystals were washed with diethyl ether to give the title compound 163 (47 mg, yield 85.6%).

¹H-NMR (MeOH-d₄, 400 MHz): δ 8.97 (2H, d, J=6.84 Hz), 8.49 (1H, d, J=8.08 Hz), 8.41 (2H, d, J=6.56 Hz), 8.23 (1H, s), 7.84 (1H, d, J=6.56 Hz), 7.56-7.61 (2H, m), 7.44 (1H, d, J=7.80 Hz), 7.28 (1H, dd, J=7.32 Hz, J=7.32 Hz), 7.12 (1H, d, J=7.80 Hz), 2.23 (3H, s), 2.22 (3H, s)

Mass spectrometric value (ESI-MS) 371 (M−1)

Compound 164 N-[2-(4-Methyl-benzylidene-hydrazinocarbonyl)-phenyl]-nicotinamide hydrochloride

The title compound 164 was produced in the same manner as in Example 3.

¹H-NMR (MeOH-d₄, 400 MHz): δ 9.22 (1H, s), 8.87 (1H, d, J=5.4 Hz), 8.83 (1H, d, J=8.04 Hz), 8.43 (1H, d, J=8.32 Hz), 8.25 (1H, s), 7.97-8.04 (1H, m), 7.81 (1H, dd, J=1.24 Hz, J=7.84 Hz), 7.64 (2H, d, J=8.04 Hz), 7.54-7.60 (1H, m), 7.23-7.29 (1H, m), 7.18 (2H, d, J=7.80 Hz), 2.29 (3H, s)

Mass spectrometric value (ESI-MS) 357 (M−1)

Compound 165 N-[2-(3,4-Dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-nicotinamide hydrochloride

The title compound 165 was produced in the same manner as in Example 3.

¹H-NMR (CDCl₃, 400 MHz): δ 9.92 (1H, s), 9.29 (1H, s), 8.75-8.78 (2H, m), 8.30-8.40 (1H, m), 8.15 (1H, s), 7.55-7.65 (5H, m), 7.42-7.49 (2H, m), 7.15-7.25 (1H, m), 2.32 (3H, s), 2.29 (3H, s)

Mass spectrometric value (ESI-MS) 371 (M−1)

Compound 166 N-[4-Bromo-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-isonicotinamide

The title compound 166 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 439 (M−1)

Compound 167 N-[4-Bromo-2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-isonicotinamide

The title compound 167 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 439 (M−1)

Compound 168 N-[4-Bromo-2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-isonicotinamide

The title compound 168 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 437 (M−1)

Compound 169 N-[4-Bromo-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-isonicotinamide

The title compound 169 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 435, 437 (M−1)

Compound 170 N-[4-Bromo-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-isonicotinamide

The title compound 170 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 451, 452 (M−1)

Compound 171 N-[4-Bromo-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-isonicotinamide

The title compound 171 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 525, 527 (M−1)

Compound 172 N-[4-Bromo-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-nicotinamide

The title compound 172 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 441, 442 (M−1)

Compound 173 N-[4-Bromo-2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-nicotinamide

The title compound 173 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 439 (M−1)

Compound 174 N-[4-Bromo-2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-nicotinamide

The title compound 174 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 435 (M−1)

Compound 175 N-[4-Bromo-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-nicotinamide

The title compound 175 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 437, 438 (M−1)

Compound 176 N-[4-Bromo-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-nicotinamide

The title compound 176 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 451, 452 (M−1)

Compound 177 N-[4-Bromo-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-nicotinamide

The title compound 177 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 524, 525 (M−1)

Compound 178 N-[4-Bromo-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-4-ethyl-benzamide

The title compound 178 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 466, 468 (M−1)

Compound 179 N-[4-Bromo-2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-4-ethyl-benzamide

The title compound 179 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 466 (M−1)

Compound 180 N-[4-Bromo-2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-ethyl-benzamide

The title compound 180 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 462 (M−1)

Compound 181 N-[4-Bromo-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-ethyl-benzamide

The title compound 181 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 462, 464 (M−1)

Compound 182 N-[4-Bromo-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-ethyl-benzamide

The title compound 182 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 476, 478 (M−1)

Compound 183 N-[4-Bromo-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-ethyl-benzamide

The title compound 183 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 550 (M−1)

Compound 184 N-[4-Chloro-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-nicotinamide

The title compound 184 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 395, 397 (M−1)

Compound 185 N-[4-Chloro-2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-nicotinamide

The title compound 185 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 395 (M−1)

Compound 186 N-[4-Chloro-2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-nicotinamide

The title compound 186 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 391 (M−1)

Compound 187 N-[4-Chloro-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-nicotinamide

The title compound 187 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 391 (M−1)

Compound 188 N-[4-Chloro-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-nicotinamide

The title compound 188 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 405, 407 (M−1)

Compound 189 N-[4-Chloro-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-nicotinamide

The title compound 189 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 479, 480 (M−1)

Compound 190 N-[4-Chloro-2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-isonicotinamide

The title compound 190 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 395, 397 (M−1)

Compound 191 N-[4-Chloro-2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-isonicotinamide

The title compound 191 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 391 (M−1)

Compound 192 N-[4-Chloro-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-isonicotinamide

The title compound 192 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 391 (M−1)

Compound 193 N-[4-Chloro-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-isonicotinamide

The title compound 193 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 405 (M−1)

Compound 194 N-[4-Chloro-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-isonicotinamide

The title compound 194 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 479 (M−1)

Example 4

Compound 195 N-[4-Bromo-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-3-(pyridin-4-ylsulfanylmethyl)-benzamide

Methyl 2-amino-5-bromobenzoate (compound A) (2.0 g) was dissolved in anhydrous methylene chloride (40.0 ml). Subsequently, pyridine (1.0 ml) and 3-(chloromethyl)benzoyl chloride (compound B) (2.0 g) were added to the solution at room temperature, and the mixture was stirred at that temperature for 3 hr. After the completion of the reaction, distilled water was added thereto, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with a saturated aqueous sodium chloride solution, was dried over sodium sulfate and was then concentrated to give methyl 5-bromo-2-[3-(chloromethyl)benzoyl]aminobenzoate as a useful intermediate (3.32 g, yield 100%).

Subsequently, methyl 5-bromo-2-[3-(chloromethyl)benzoyl]aminobenzoate (1.5 g) was dissolved in anhydrous methylene chloride. Triethylamine (2.0 ml) and 4-mercaptopyridine (compound B′) (880 mg) were added to the solution at room temperature, and the mixture was stirred at that temperature for 12 hr. After the completion of the reaction, distilled water was added thereto at room temperature, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with a saturated aqueous sodium chloride solution, was dried over sodium sulfate, and was then concentrated. Diethyl ether was added to the residue for crystallization. The crystals were filtered through Kiriyama Rohto (21 mmφ) and were washed with diethyl ether to give methyl 5-bromo-2-(3-[(4-pyridylsulfanyl)methyl]benzoylamino)benzoate (1.20 g, yield 67%) as a useful intermediate.

Methyl 5-bromo-2-(3-[(4-pyridylsulfanyl)methyl]benzoylamino)-benzoate (1.20 g) obtained by the above reaction was dissolved in ethanol (25.0 ml). Hydrazine monohydrate (2.0 ml) was added to the solution at room temperature, and the mixture was heated under reflux with stirring for one hr. After the completion of the reaction, the reaction solution was allowed to cool at room temperature, was cooled under ice cooling to precipitate crystals. The precipitated crystals were filtered through Kiriyama Rohto (21 mmφ) and were washed with diethyl ether to give N-(4-bromo-2-hydrazinocarbonyl-phenyl)-3-(pyridin-4-ylsulfanylmethyl)-benzamide (753 mg, yield 65.4%) as a hydrazine compound.

N-(4-Bromo-2-hydrazinocarbonyl-phenyl)-3-(pyridin-4-ylsulfanylmethyl)-benzamide (50.0 mg) was dissolved in anhydrous toluene (1.0 ml). Subsequently, a catalytic amount of acetic acid and 3-fluorobenzaldehyde (compound C) (50.0 μl) were added to the solution at room temperature, and the mixture was heated under reflux with stirring for one hr. After the completion of the reaction, the reaction solution was allowed to cool at room temperature and was ice-cooled to precipitate crystals. The precipitated crystals were filtered through Kiriyama Rohto (21 mmφ), were washed with toluene and hexane, and were dried through a vacuum pump to give the title compound 195 (27.0 mg, yield 43.6%).

Mass spectrometric value (ESI-MS) 561, 563 (M−1)

Compound 196 N-[4-Bromo-2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-3-(pyridin-4-ylsulfanylmethyl)-benzamide

The title compound 196 was produced in the same manner as in Example 4.

Mass spectrometric value (ESI-MS) 563 (M−1)

Compound 197 N-[4-Bromo-2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-(pyridin-4-ylsulfanylmethyl)-benzamide

The title compound 197 was produced in the same manner as in Example 4.

Mass spectrometric value (ESI-MS) 559 (M−1)

Compound 198 N-[4-Bromo-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-(pyridin-4-ylsulfanylmethyl)-benzamide

The title compound 198 was produced in the same manner as in Example 4.

Mass spectrometric value (ESI-MS) 559 (M−1)

Compound 199 N-[4-Bromo-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-(pyridin-4-ylsulfanylmethyl)-benzamide

The title compound 199 was produced in the same manner as in Example 4.

Mass spectrometric value (ESI-MS) 571 (M−1)

Compound 200 N-[4-Bromo-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-(pyridin-4-ylsulfanylmethyl)-benzamide

The title compound 200 was produced in the same manner as in Example 4.

Mass spectrometric value (ESI-MS) 647 (M−1)

Compound 201 N-[4-Bromo-2-(1-methyl-1H-pyrrol-2-ylmethylene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 201 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 484 (M−1)

Compound 202 N-[4-Bromo-2-(4,5-dimethyl-furan-2-ylmethylene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 202 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 499 (M−1)

Compound 203 N-[2-(4-Methyl-benzylidene-hydrazinocarbonyl)-phenyl]-isonicotinamide hydrochloride

The title compound 203 was produced in the same manner as in Example 3.

¹H-NMR (CD₃OD, 400 MHz): δ 8.92-8.98 (2H, m), 8.49 (1H, d, J=8.6 Hz), 8.34-8.40 (2H, m), 8.26 (1H, s), 8.81-8.87 (1H, m), 7.64 (2H, d, J=8.0 Hz), 7.55-7.61 (1H, m), 7.25-7.31 (1H, m), 7.15-7.20 (2H, m), 2.30 (3H, s)

Mass spectrometric value (ESI-MS) 357 (M−1)

Compound 204 N-[2-(3-Fluoro-benzylidene-hydrazinocarbonyl)-4-iodo-phenyl]-3,4-dimethoxy-benzamide

The title compound 204 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 546 (M−1)

Compound 205 N-[2-(4-Fluoro-benzylidene-hydrazinocarbonyl)-4-iodo-phenyl]-3,4-dimethoxy-benzamide

The title compound 205 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 546 (M−1)

Compound 206 N-[4-Iodo-2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 206 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 542 (M−1)

Compound 207 N-[4-Iodo-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 207 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 542 (M−1)

Compound 208 N-[2-(3,4-Dimethyl-benzylidene-hydrazinocarbonyl)-4-iodo-phenyl]-3,4-dimethoxy-benzamide

The title compound 208 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 556 (M−1)

Compound 209 N-[2-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-iodo-phenyl]-3,4-dimethoxy-benzamide

The title compound 209 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 630 (M−1)

Compound 210 N-[2-(1-Methyl-1H-pyrrol-2-ylmethylene-hydrazinocarbonyl)-phenyl]-isonicotinamide

The title compound 210 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 346 (M−1)

Compound 211 N-[4-Bromo-2-(1-methyl-1H-pyrrol-2-ylmethylene-hydrazinocarbonyl)-phenyl]-nicotinamide

The title compound 211 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 424 (M−1)

Compound 212 N-[4-Chloro-2-(1-methyl-1H-pyrrol-2-ylmethylene-hydrazinocarbonyl)-phenyl]-nicotinamide

The title compound 212 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 380 (M−1)

Compound 213 N-{2-[1-(3-Fluoro-phenyl)-ethylidene-hydrazinocarbonyl]-phenyl}-3,4-dimethoxy-benzamide

The title compound 213 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 434 (M−1)

Compound 214 N-{4-Bromo-2-[1-(3-fluoro-phenyl)-ethylidene-hydrazinocarbonyl]-phenyl}-3,4-dimethoxy-benzamide

The title compound 214 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 512, 514 (M−1)

Compound 215 N-[4-Bromo-2-(1-m-toluyl-ethylidene-hydrazinocarbonyl)-phenyl]-nicotinamide

The title compound 215 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 449, 451 (M−1)

Compound 216 N-[4-Bromo-2-(1-p-toluyl-ethylidene-hydrazinocarbonyl)-phenyl]-nicotinamide

The title compound 216 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 449 (M−1)

Compound 217 N-[4-Chloro-2-(1-p-toluyl-ethylidene-hydrazinocarbonyl)-phenyl]-nicotinamide

The title compound 217 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 405 (M−1)

Compound 218 N-[2-(4,5-Dimethyl-furan-2-ylmethylene-hydrazinocarbonyl)-phenyl]-nicotinamide

The title compound 218 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 361 (M−1)

Compound 219 N-[2-(4,5-Dimethyl-furan-2-ylmethylene-hydrazinocarbonyl)-phenyl]-isonicotinamide

The title compound 219 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 361 (M−1)

Compound 220 N-[4-Bromo-2-(4,5-dimethyl-furan-2-ylmethylene-hydrazinocarbonyl)-phenyl]-nicotinamide

The title compound 220 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 439 (M−1)

Compound 221 N-[4-Bromo-2-(4,5-dimethyl-furan-2-ylmethylene-hydrazinocarbonyl)-phenyl]-isonicotinamide

The title compound 221 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 439, 441 (M−1)

Compound 222 N-[4-Chloro-2-(4,5-dimethyl-furan-2-ylmethylene-hydrazinocarbonyl)-phenyl]-nicotinamide

The title compound 222 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 395 (M−1)

Compound 223 N-[4-Chloro-2-(4,5-dimethyl-furan-2-ylmethylene-hydrazinocarbonyl)-phenyl]-isonicotinamide

The title compound 223 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 395 (M−1)

Compound 224 N-[2-(Benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 224 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 342 (M−1)

Compound 225 N-[2-(2-Fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 225 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 360 (M−1)

Compound 226 N-[2-(3-Fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 226 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 360 (M−1)

Compound 227 N-[2-(Benzylidene-hydrazinocarbonyl)-4,5-dimethoxy-phenyl]-3,4-dimethoxy-benzamide

The title compound 227 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 462 (M−1)

Compound 228 N-[2-(2-Bromo-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 228 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 421 (M−1)

Compound 229 N-[2-(2-Methyl-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 229 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 356 (M−1)

Compound 230 N-[4,5-Dimethoxy-2-(2-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 230 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 476 (M−1)

Compound 231 N-[2-(2-Chloro-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 231 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 436 (M−1)

Compound 232 3,4-Dimethoxy-N-[2-(6-methoxy-naphthalen-2-ylmethylene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 232 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 482 (M−1)

Compound 233 N-[2-(Biphenyl-4-ylmethylene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 233 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 478 (M−1)

Compound 234 N-[2-(4-Bromo-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 234 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 480 (M−1)

Compound 235 N-[2-(3-Phenyl-allylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 235 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 368 (M−1)

Compound 236 2-Fluoro-N-[2-(2-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 236 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 378 (M−1)

Compound 237 2-Fluoro-N-[2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 237 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 378 (M−1)

Compound 238 2-Fluoro-N-[2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 238 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 374 (M−1)

Compound 239 N-[2-(3-Tert-butyl-2-hydroxy-benzylidene-hydrazinocarbonyl)-phenyl]-2-fluoro-benzamide

The title compound 239 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 432 (M−1)

Compound 240 3,4-Dimethoxy-N-[2-(4-nitro-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 240 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 447 (M−1)

Compound 241 N-[2-(4-Diethylamino-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 241 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 473 (M−1)

Compound 242 N-[2-(3-Fluoro-benzylidene-hydrazinocarbonyl)-4-hydroxy-phenyl]-3,5-dimethoxy-benzamide

The title compound 242 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 436, 437 (M−1)

Compound 243 N-[4-Bromo-2-(pyridin-2-ylmethylene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 243 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 483 (M−1)

Compound 244 N-[4-Chloro-2-(pyridin-2-ylmethylene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 244 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 437 (M−1)

Compound 245 3,4-Dimethoxy-N-[2-pyridin-2-ylmethylene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 245 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 403 (M−1)

Compound 246 N-[4-Chloro-2-(6-methyl-pyridin-2-ylmethylene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide

The title compound 246 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 451 (M−1)

Compound 247 3,4-Dimethoxy-N-[2-(6-methyl-pyridin-2-ylmethylene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 247 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 417 (M−1)

Compound 248 N-[4-Bromo-2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-tert-butyl-benzamide

The title compound 248 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 490, 492 (M−1)

Compound 249 N-[2-(1-m-Toluyl-ethylidene-hydrazinocarbonyl)-phenyl]-isonicotinamide

The title compound 249 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 371 (M−1)

Compound 250 N-[4-Chloro-2-(1-m-toluyl-ethylidene-hydrazinocarbonyl)-phenyl]-nicotinamide

The title compound 250 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 405 (M−1)

Compound 251 N-[2-(1-p-Toluyl-ethylidene-hydrazinocarbonyl)-phenyl]-nicotinamide

The title compound 251 was produced in the same manner as in Example 1.

Mass spectrometric value (ESI-MS) 371 (M−1)

Compound 252 N-[4-Bromo-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-nicotinamide hydrochloride

The title compound 252 was produced in the same manner as in Example 3.

¹H-NMR (MeOH-d₄, 400 MHz): δ 9.21-9.25 (1H, m), 8.79-8.93 (2H, m), 8.34-8.39 (1H, m), 8.25 (1H, s), 8.01 (1H, d, J=2.2 Hz), 8.00-8.15 (1H, m), 7.71 (1H, dd, J=8.08 Hz, J=2.20 Hz), 7.63 (2H, d, J=8.32 Hz), 7.18 (2H, d, J=8.08 Hz), 2.29 (3H, s)

Mass spectrometric value (ESI-MS) 437, 438 (M−1)

Compound 253 N-[2-(3-Methyl-benzylidene-hydrazinocarbonyl)-phenyl]-isonicotinamide hydrochloride

The title compound 253 was produced in the same manner as in Example 3.

¹H-NMR (CDCl₃, 400 MHz): δ 8.96-8.99 (2H, m), 8.49 (1H, d, J=8.08 Hz), 8.42 (2H, dd, J=1.20 Hz, J=5.60 Hz), 8.27 (1H, s), 7.85 (1H, dd, J=1.20 Hz, J=7.80 Hz), 7.51-7.61 (3H, m), 7.18-7.31 (3H, m), 2.30 (3H, s)

Mass spectrometric value (ESI-MS) 357 (M−1)

Compound 255 N-[4-Bromo-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-4-(pyridin-4-ylsulfanylmethyl)-benzamide

The title compound 255 was produced in the same manner as in Example 4.

Mass spectrometric value (ESI-MS) 563 (M−1)

Compound 256 N-[4-Bromo-2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-4-(pyridin-4-ylsulfanylmethyl)-benzamide

The title compound 256 was produced in the same manner as in Example 4.

Mass spectrometric value (ESI-MS) 563 (M−1)

Compound 257 N-[4-Bromo-2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-(pyridin-4-ylsulfanylmethyl)-benzamide

The title compound 257 was produced in the same manner as in Example 4.

Mass spectrometric value (ESI-MS) 559 (M−1)

Compound 258 N-[4-Bromo-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-(pyridin-4-ylsulfanylmethyl)-benzamide

The title compound 258 was produced in the same manner as in Example 4.

Mass spectrometric value (ESI-MS) 559 (M−1)

Compound 259 N-[4-Bromo-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-(pyridin-4-ylsulfanylmethyl)-benzamide

The title compound 259 was produced in the same manner as in Example 4.

Mass spectrometric value (ESI-MS) 571 (M−1)

Compound 260 N-[4-Bromo-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-(pyridin-4-ylsulfanylmethyl)-benzamide

The title compound 260 was produced in the same manner as in Example 4.

Mass spectrometric value (ESI-MS) 645, 647 (M−1)

Compound 261 N-[4-Bromo-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-4-(2-hydroxy-ethylsulfanylmethyl)-benzamide

The title compound 261 was produced in the same manner as in Example 4.

Mass spectrometric value (ESI-MS) 530 (M−1)

Compound 262 N-[4-Bromo-2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-4-(2-hydroxy-ethylsulfanylmethyl)-benzamide

The title compound 262 was produced in the same manner as in Example 4.

Mass spectrometric value (ESI-MS) 530 (M−1)

Compound 263 N-[4-Bromo-2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-(2-hydroxy-ethylsulfanylmethyl)-benzamide

The title compound 263 was produced in the same manner as in Example 4.

Mass spectrometric value (ESI-MS) 524 (M−1)

Compound 264 N-[4-Bromo-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-(2-hydroxy-ethylsulfanylmethyl)-benzamide

The title compound 264 was produced in the same manner as in Example 4.

Mass spectrometric value (ESI-MS) 526 (M−1)

Compound 265 N-[4-Bromo-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-(2-hydroxy-ethylsulfanylmethyl)-benzamide

The title compound 265 was produced in the same manner as in Example 4.

Mass spectrometric value (ESI-MS) 540 (M−1)

Compound 266 N-[4-Bromo-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-(2-hydroxy-ethylsulfanylmethyl)-benzamide

The title compound 266 was produced in the same manner as in Example 4.

Mass spectrometric value (ESI-MS) 612, 614 (M−1)

Compound 267 N-[4-Bromo-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-(1H-[1,2,4]triazol-3-ylsulfanylmethyl)-benzamide

The title compound 267 was produced in the same manner as in Example 4.

¹H-NMR (CD₃OD, 400 MHz): δ 8.60 (1H, d, J=9.0 Hz), 8.31 (1H, s), 8.28 (1H, bs), 8.05 (1H, d, J=2.2 Hz), 8.01 (1H, m), 7.86 (1H, m), 7.73 (1H, dd, J=9.0 Hz, J=2.2 Hz), 7.60 (2H, m), 7.52 (1H, m), 7.46 (1H, t, J=7.7 Hz), 7.19 (1H, d, J=7.8 Hz), 4.44 (2H, s), 2.30 (6H, s)

Mass spectrometric value (ESI-MS) 561 (M−1)

Compound 268 N-[4-Bromo-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-(1H-[1,2,4]triazol-3-ylsulfanylmethyl)-benzamide

The title compound 268 was produced in the same manner as in Example 4.

¹H-NMR (CD₃OD, 400 MHz): δ 2.38 (3H, s), 4.44 (2H, s), 7.26 (1H, d, J=7.4 Hz), 7.46 (2H, m), 7.59 (1H, m), 7.66 (1H, dd, J=9.0 Hz, J=2.4 Hz), 7.72 (1H, m), 7.86 (2H, m), 7.97-8.05 (2H, m), 8.29-8.34 (2H, m), 8.57 (1H, d, J=8.8 Hz)

Mass spectrometric value (ESI-MS) 547 (M−1)

Compound 269 N-[4-Bromo-2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-(1H-[1,2,4]triazol-3-ylsulfanylmethyl)-benzamide

The title compound 269 was produced in the same manner as in Example 4.

¹H-NMR (DMSO-d₆, 400 MHz): δ 2.48-2.53 (3H, m), 4.43 (2H, s), 7.27-7.82 (9H, m), 7.96 (3H, m), 8.57 (1H, d, J=9.0 Hz)

Mass spectrometric value (ESI-MS) 549 (M−1)

Compound 270 N-[4-Bromo-2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-3-(1H-[1,2,4]triazol-3-ylsulfanylmethyl)-benzamide

The title compound 270 was produced in the same manner as in Example 4.

¹H-NMR (CD₃OD, 400 MHz): δ 4.44 (2H, s), 7.20 (1H, m), 7.45 (1H, m), 7.59 (1H, m), 7.66 (1H, dd, J=9.0 Hz, J=2.3 Hz), 7.75 (1H, dd, J=9.0 Hz, J=2.3 Hz), 7.87 (2H, m), 7.99-8.06 (3H, m), 8.30 (1H, s), 8.36 (1H, s), 8.57 (1H, m)

Mass spectrometric value (ESI-MS) 553 (M−1)

Compound 271 N-[4-Bromo-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-3-(1H-[1,2,4]triazol-3-ylsulfanylmethyl)-benzamide

The title compound 271 was produced in the same manner as in Example 4.

¹H-NMR (CD₃OD, 400 MHz): δ 4.44 (2H, s), 7.19 (1H, m), 7.45 (2H, m), 7.59-7.77 (3H, m), 7.86 (2H, m), 7.97-8.01 (2H, m), 8.29-8.36 (2H, m), 8.58 (1H, m)

Mass spectrometric value (ESI-MS) 553 (M−1)

Compound 272 N-[4-Bromo-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-(1H-[1,2,4]triazol-3-ylsulfanylmethyl)-benzamide

The title compound 272 was produced in the same manner as in Example 4.

¹H-NMR (CD₃OD, 400 MHz): δ 4.44 (2H, s), 7.45 (1H, m), 7.59 (1H, m), 7.67 (1H, m), 7.76 (1H, dd, J=9.0 Hz, J=2.2 Hz), 7.85 (2H, m), 7.97-8.06 (3H, m), 8.29 (1H, s), 8.39 (1H, s), 8.57 (1H, dd, J=9.0 Hz, J=1.7 Hz)

Mass spectrometric value (ESI-MS) 635 (M−1)

Compound 273 N-[4-Bromo-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-(3-hydroxy-propylsulfanylmethyl)-benzamide

The title compound 273 was produced in the same manner as in Example 4.

¹H-NMR (CD₃OD, 400 MHz): δ 1.76 (2H, m), 2.31 (3H, s), 2.32 (3H, s), 2.50 (2H, t, J=7.0 Hz), 3.60 (2H, t, J=6.3 Hz), 3.80 (2H, s), 7.20 (1H, d, J=7.3 Hz), 7.52 (3H, m), 7.66 (1H, s), 7.74 (1H, dd, J=9.0 Hz, J=2.2 Hz), 7.96 (2H, d, J=8.3 Hz), 8.05 (1H, d, J=2.2 Hz), 8.30 (1H, s), 8.63 (1H, d, J=9.0 Hz)

Mass spectrometric value (ESI-MS) 552 (M−1)

Compound 274 N-[4-Bromo-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-(3-hydroxy-propylsulfanylmethyl)-benzamide

The title compound 274 was produced in the same manner as in Example 4.

¹H-NMR (CD₃OD, 400 MHz): δ 1.76 (2H, m), 2.39 (3H, s), 2.50 (2H, t, J=7.3 Hz), 3.60 (2H, t, J=6.1 Hz), 3.80 (2H, s), 7.27 (2H, d, J=8.1 Hz), 7.52 (2H, d, J=8.0 Hz), 7.74 (3H, m), 7.96 (2H, d, J=8.1 Hz), 8.01 (1H, m), 8.33 (1H, s), 8.63 (1H, d, J=8.8 Hz)

Mass spectrometric value (ESI-MS) 538 (M−1)

Compound 275 N-[4-Bromo-2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-(3-hydroxy-propylsulfanylmethyl)-benzamide

The title compound 275 was produced in the same manner as in Example 4.

¹H-NMR (CD₃OD, 400 MHz): δ 1.76 (2H, m), 2.40 (3H, s), 2.51 (2H, t, J=7.1 Hz), 3.60 (2H, t, J=6.3 Hz), 3.81 (2H, s), 7.25-7.35 (2H, m), 7.52 (2H, m), 7.63 (1H, m), 7.71-7.77 (2H, m), 7.96 (2H, d, J=8.0 Hz), 8.06 (1H, s), 8.34 (1H, s), 8.62 (1H, m)

Mass spectrometric value (ESI-MS) 538 (M−1)

Compound 276 N-[4-Bromo-2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-4-(3-hydroxy-propylsulfanylmethyl)-benzamide

The title compound 276 was produced in the same manner as in Example 4.

¹H-NMR (CD₃OD, 400 MHz): δ 1.76 (2H, m), 2.51 (2H, m), 3.60 (2H, m), 3.81 (2H, m), 7.19 (2H, m), 7.51 (2H, m), 7.75-8.06 (6H, m), 8.35 (1H, m), 8.60 (1H, m)

Mass spectrometric value (ESI-MS) 542 (M−1)

Compound 277 N-[4-Bromo-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-4-(3-hydroxy-propylsulfanylmethyl)-benzamide

The title compound 277 was produced in the same manner as in Example 4.

¹H-NMR (CD₃OD, 400 MHz): δ 1.76 (2H, m), 2.51 (2H, t, J=7.3 Hz), 3.60 (2H, t, J=6.4 Hz), 3.81 (2H, s), 7.19 (1H, m), 7.46-7.54 (3H, m), 7.60 (1H, m), 7.70 (1H, m), 7.77 (1H, dd, J=9.1 Hz, J=2.3 Hz), 7.96 (2H, m), 8.07 (1H, s), 8.35 (1H, s), 8.62 (1H, d, J=9.1 Hz)

Mass spectrometric value (ESI-MS) 542 (M−1)

Compound 278 N-[4-Bromo-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-(3-hydroxy-propylsulfanylmethyl)-benzamide

The title compound 278 was produced in the same manner as in Example 4.

¹H-NMR (CD₃OD, 400 MHz): δ 1.76 (2H, m), 2.50 (2H, t, J=7.3 Hz), 3.60 (2H, t, J=6.3 Hz), 3.80 (2H, s), 7.52 (2H, d, J=8.0 Hz), 7.69 (1H, d, J=8.3 Hz), 7.76 (1H, dd, J=8.8 Hz, J=2.0 Hz), 7.95 (2H, d, J=8.3 Hz), 8.05-8.07 (2H, m), 8.33 (1H, s), 8.39 (1H, s), 8.62 (1H, d, J=9.0 Hz)

Mass spectrometric value (ESI-MS) 626 (M−1)

Example 5

Compound 279 N-[4-Bromo-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-[(2-morpholin-4-yl-ethylamino)-methyl]-benzamide

Methyl 2-amino-5-bromobenzoate (compound A) (3.0 g) was dissolved in anhydrous methylene chloride (40.0 ml). Subsequently, pyridine (2.1 ml) and 4-(chloromethyl)benzoyl chloride (compound B) (2.2 ml) were added to the solution at room temperature, and the mixture was stirred at that temperature for one hr. After the completion of the reaction, distilled water was added, followed by separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated to give methyl 5-bromo-2-[3-(chloromethyl)benzoyl]aminobenzoate as a useful intermediate (4.90 g, yield 100%).

Methyl 5-bromo-2-[3-(chloromethyl)benzoyl]aminobenzoate (500 mg) obtained by the above reaction was dissolved in anhydrous methylene chloride (3.0 ml), triethylamine (545 μl) and 4-(2-aminoethyl)morpholine (compound B′) (341 μl) were added to the solution at room temperature, and the mixture was stirred at room temperature for 15 hr. After the completion of the reaction, water was added at room temperature, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, dried over sodium sulfate, and was then concentrated. The residue was purified by column chromatography eluted with a chloroform methanol system to give methyl 5-bromo-2-[(3{[(2-morpholinoethyl)amino]methyl}benzoyl)amino]benzoate as a useful intermediate (306 mg, yield 50%).

Methyl 5-bromo-2-[(3{[(2-morpholinoethyl)amino]methyl}benzoyl)-amino]benzoate obtained by the above reaction was dissolved in ethanol (5.0 ml), hydrazine monohydrate (650 μl) was added to the solution, and the mixture was stirred at room temperature for 15 hr. After the completion of the reaction, water was added thereto at room temperature, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated to give N-(4-bromo-2-hydrazinocarbonyl-phenyl)-3-[(2-morpholin-4-yl-ethylamino)-methyl]-benzamide as a hydrazine compound (220 mg, crude yield 75%).

N-(4-Bromo-2-hydrazinocarbonyl-phenyl)-3-[(2-morpholin-4-yl-ethylamino)-methyl]-benzamide (25 mg) was dissolved in anhydrous toluene (1.0 ml), a catalytic amount of acetic acid and 3,4-dimethylbenzaldehyde (compound C) (10.0 μl) were added to the solution at room temperature, and the mixture was stirred at room temperature for 15 hr. After the completion of the reaction, the product was purified by column chromatography eluted with a chloroform methanol system to give the title compound 279 (21.1 mg, yield 67%).

¹H-NMR (CD₃OD, 400 MHz): δ 2.31 (3H, s), 2.32 (3H, s), 2.44 (4H, m), 2.60 (2H, t, J=6.1 Hz), 2.97 (2H, t, J=6.1 Hz), 3.65 (4H, t, J=4.6 Hz), 4.15 (2H, s), 7.20 (1H, d, J=7.8 Hz), 7.54 (1H, m), 7.59-7.70 (3H, m), 7.76 (1H, dd, J=9.0 Hz, J=2.2 Hz), 8.30 (2H, m), 8.07 (1H, d, J=2.2 Hz), 8.32 (1H, s), 8.64 (1H, d, J=9.0 Hz)

Mass spectrometric value (ESI-MS) 594 (M+1)

Compound 280 N-[4-Bromo-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 280 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 1.12 (6H, t, J=7.1 Hz), 2.27 (6H, s), 2.28 (3H, s), 2.60 (2H, t, J=7.3 Hz), 2.77 (4H, q, J=7.3 Hz), 2.88 (2H, t, J=7.3 Hz), 3.63 (2H, s), 7.16 (1H, d, J=7.8 Hz), 7.50 (3H, m), 7.61 (1H, s), 7.70 (1H, dd, J=9.0 Hz, J=2.2 Hz), 7.97 (2H, d, J=8.3 Hz), 8.02 (1H, d, J=2.2 Hz), 8.30 (1H, s), 8.61 (1H, d, J=9.0 Hz)

Mass spectrometric value (ESI-MS) 594 (M+1)

Compound 281 N-[4-Bromo-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-[(2-morpholin-4-yl-ethylamino)-methyl]-benzamide

The title compound 281 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 2.29 (3H, s), 2.30 (3H, s), 2.43 (4H, m), 2.54 (2H, t, J=6.0 Hz), 2.72 (2H, t, J=6.0 Hz), 3.70 (4H, t, J=4.6 Hz), 3.89 (2H, s), 7.18 (1H, d, J=7.8 Hz), 7.44-7.70 (6H, m), 7.99 (2H, d, J=7.8 Hz), 8.31 (1H, s), 8.55 (1H, d, J=8.3 Hz)

Mass spectrometric value (ESI-MS) 592 (M+1)

Compound 282 N-[4-Bromo-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-[(2-morpholin-4-yl-ethylamino)-methyl]-benzamide

The title compound 282 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 2.39 (3H, s), 2.43 (4H, m), 2.53 (2H, t, J=5.9 Hz), 2.72 (2H, t, J=5.9 Hz), 3.70 (4H, t, J=4.6 Hz), 3.89 (2H, s), 7.23 (2H, d, J=8.0 Hz), 7.45 (2H, d, J=8.0 Hz), 7.56 (1H, m), 7.70 (3H, m), 7.99 (2H, m), 8.34 (1H, s), 8.56 (1H, d, J=9.0 Hz)

Mass spectrometric value (ESI-MS) 576 (M−1)

Compound 283 N-[4-Bromo-2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-[(2-morpholin-4-yl-ethylamino)-methyl]-benzamide

The title compound 283 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 2.38 (3H, s), 2.43 (4H, m), 2.52 (2H, t, J=6.0 Hz), 2.70 (2H, t, J=6.0 Hz), 3.70 (4H, t, J=4.4 Hz), 3.88 (2H, s), 7.22-7.32 (2H, m), 7.44 (2H, d, J=8.3 Hz), 7.52 (2H, m), 7.69 (2H, s), 8.00 (2H, d, J=7.8 Hz), 8.42 (2H, m)

Mass spectrometric value (ESI-MS) 578 (M−1)

Compound 284 N-[4-Bromo-2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-4-[(2-morpholin-4-yl-ethylamino)-methyl]-benzamide

The title compound 284 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 2.43 (4H, m), 2.52 (2H, t, J=6.0 Hz), 2.70 (2H, t, J=6.0 Hz), 3.70 (4H, t, J=4.5 Hz), 3.89 (2H, s), 7.12 (2H, m), 7.45 (2H, d, J=8.3 Hz), 7.54 (1H, m), 7.67 (1H, m), 7.82 (2H, m), 8.00 (2H, d, J=7.8 Hz), 8.39 (1H, s), 8.48 (1H, m)

Mass spectrometric value (ESI-MS) 582 (M−1)

Compound 285 N-[4-Bromo-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 285 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 1.04 (6H, t, J=7.2 Hz), 2.21 (3H, s), 2.33 (3H, s), 2.51-2.66 (8H, m), 3.55 (2H, s), 7.18 (2H, d, J=8.0 Hz), 7.43 (3H, m), 7.66 (2H, d, J=8.0 Hz), 7.74 (1H, m), 7.98 (2H, d, J=8.0 Hz), 8.36 (1H, d, J=9.0 Hz), 8.49 (1H, s)

Mass spectrometric value (ESI-MS) 576 (M−1)

Compound 286 N-[4-Bromo-2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 286 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 1.04 (6H, t, J=7.1 Hz), 2.23 (3H, s), 2.40 (3H, s), 2.52-2.66 (8H, m), 3.59 (2H, s), 7.24-7.33 (2H, m), 7.45 (2H, d, J=8.3 Hz), 7.56 (2H, m), 7.70 (2H, m), 8.00 (2H, d, J=7.6 Hz), 8.38 (1H, s), 8.50 (1H, d, J=9.0 Hz)

Mass spectrometric value (ESI-MS) 578 (M−1)

Compound 287 N-[4-Bromo-2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-4-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 287 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 1.04 (6H, t, J=7.1 Hz), 2.23 (3H, s), 2.54-2.66 (8H, m), 3.59 (2H, s), 7.12 (2H, m), 7.45 (2H, d, J=8.3 Hz), 7.54 (1H, m), 7.68 (1H, s), 7.83 (2H, m), 7.99 (2H, d, J=7.8 Hz), 8.42 (1H, s), 8.47 (1H, d, J=9.0 Hz)

Mass spectrometric value (ESI-MS) 580 (M−1)

Compound 288 N-[4-Bromo-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-4-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 288 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 1.04 (6H, t, J=7.1 Hz), 2.22 (3H, s), 2.52-2.66 (8H, m), 3.58 (2H, s), 7.10 (1H, m), 7.34-7.46 (4H, m), 7.55 (2H, m), 7.68 (1H, s), 7.99 (2H, d, J=7.8 Hz), 8.29 (1H, d, J=8.8 Hz), 8.52 (1H, s)

Mass spectrometric value (ESI-MS) 582 (M−1)

Compound 289 N-[4-Bromo-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 289 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 1.04 (6H, t, J=7.1 Hz), 2.23 (3H, s), 2.53-2.66 (8H, m), 3.60 (2H, s), 7.48 (3H, m), 7.58 (1H, d, J=8.3 Hz), 7.67 (1H, s), 7.98-8.07 (4H, m), 8.56 (1H, m), 8.52 (1H, m)

Mass spectrometric value (ESI-MS) 664 (M−1)

Compound 290 N-[4-Bromo-2-(4-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-4-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 290 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 1.04 (6H, t, J=7.1 Hz), 2.21 (3H, s), 2.51-2.66 (8H, m), 3.56 (2H, s), 3.80 (3H, s), 6.89 (2H, d, J=8.8 Hz), 7.43 (3H, m), 7.71 (3H, m), 7.98 (2H, d, J=8.0 Hz), 8.38 (1H, d, J=9.0 Hz), 8.45 (1H, s)

Mass spectrometric value (ESI-MS) 594 (M−1)

Compound 291 N-[4-Bromo-2-(3-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-4-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 291 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 1.03 (6H, t, J=7.1 Hz), 2.21 (3H, s), 2.51-2.65 (8H, m), 3.56 (2H, s), 3.84 (3H, s), 6.94 (1H, m), 7.27-7.48 (6H, m), 7.75 (1H, s), 7.97 (2H, d, J=7.8 Hz), 8.41 (1H, d, J=9.0 Hz), 8.47 (1H, s)

Mass spectrometric value (ESI-MS) 592 (M−1)

Compound 292 N-[4-Bromo-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-[(2-diethylamino-ethylamino)-methyl]-benzamide

The title compound 292 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 1.05 (6H, t, J=7.2 Hz), 2.29 (3H, s), 2.30 (3H, s), 2.57-2.73 (8H, m), 3.87 (3H, s), 7.18 (1H, d, J=7.8 Hz), 7.43-7.73 (6H, m), 7.99 (2H, d, J=7.8 Hz), 8.31 (1H, s), 8.56 (1H, d, J=9.0 Hz)

Mass spectrometric value (ESI-MS) 576 (M−1)

Compound 293 N-[4-Bromo-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-[(2-diethylamino-ethylamino)-methyl]-benzamide

The title compound 293 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 1.05 (6H, t, J=7.1 Hz), 2.39 (3H, s), 2.56-2.73 (8H, m), 3.87 (2H, s), 7.22-7.27 (2H, m), 7.44 (2H, d, J=8.3 Hz), 7.57-7.71 (4H, m), 7.99 (2H, m), 8.34 (1H, s), 8.59 (1H, d, J=9.0 Hz)

Mass spectrometric value (ESI-MS) 562 (M−1)

Compound 294 N-[4-Bromo-2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-[(2-diethylamino-ethylamino)-methyl]-benzamide

The title compound 294 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 1.03 (6H, t, J=7.1 Hz), 2.39 (3H, s), 2.52-2.70 (8H, m), 3.87 (2H, s), 7.23-7.33 (2H, m), 7.45 (2H, d, J=8.3 Hz), 7.55 (2H, m), 7.70 (2H, m), 8.00 (2H, d, J=7.8 Hz), 8.38 (1H, s), 8.51 (1H, d, J=9.0 Hz)

Mass spectrometric value (ESI-MS) 562 (M−1)

Compound 295 N-[4-Bromo-2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-4-[(2-diethylamino-ethylamino)-methyl]-benzamide

The title compound 295 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 1.05 (6H, t, J=7.1 Hz), 2.55-2.72 (8H, m), 3.87 (2H, s), 7.12 (2H, m), 7.45 (2H, d, J=8.1 Hz), 7.56-7.82 (4H, m), 7.99 (2H, d, J=7.6 Hz), 8.39 (1H, s), 8.55 (1H, d, J=8.6 Hz)

Mass spectrometric value (ESI-MS) 568 (M−1)

Compound 296 N-[4-Bromo-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-4-[(2-diethylamino-ethylamino)-methyl]-benzamide

The title compound 296 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 1.04 (6H, t, J=7.1 Hz), 2.53-2.71 (8H, m), 3.88 (2H, s), 7.13 (1H, m), 7.37-7.71 (7H, m), 7.99 (2H, d, J=7.6 Hz), 8.42 (1H, s), 8.49 (1H, d, J=8.8 Hz)

Mass spectrometric value (ESI-MS) 568 (M−1)

Compound 297 N-[4-Bromo-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-[(2-diethylamino-ethylamino)-methyl]-benzamide

The title compound 297 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 1.05 (3H, t, J=7.1 Hz), 1.24 (3H, m), 2.53-2.75 (6H, m), 3.72 (2H, m), 3.87 (2H, s), 7.46 (2H, d, J=7.8 Hz), 7.56 (3H, m), 7.73 (1H, m), 7.98 (3H, m), 8.06 (1H, s), 8.48 (1H, d, J=8.3 Hz)

Mass spectrometric value (ESI-MS) 650 (M−1)

Compound 298 N-[4-Bromo-2-(4-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-4-[(2-diethylamino-ethylamino)-methyl]-benzamide

The title compound 298 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 1.05 (6H, t, J=7.2 Hz), 2.55-2.72 (8H, m), 3.85 (3H, s), 3.87 (2H, s), 6.93 (2H, d, J=8.8 Hz), 7.44 (2H, d, J=8.0 Hz), 7.58 (1H, m), 7.75 (3H, m), 7.99 (2H, d, J=7.6 Hz), 8.31 (1H, s), 8.60 (1H, d, J=9.0 Hz)

Mass spectrometric value (ESI-MS) 578 (M−1)

Compound 299 N-[4-Bromo-2-(3-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-4-[(2-diethylamino-ethylamino)-methyl]-benzamide

The title compound 299 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 1.03 (6H, t, J=7.1 Hz), 2.52-2.70 (8H, m), 3.86 (3H, s), 3.87 (2H, s), 6.97 (1H, m), 7.29-7.45 (5H, m), 7.56 (1H, s), 7.73 (1H, m), 7.99 (2H, d, J=8.0 Hz), 8.39 (1H, s), 8.53 (1H, m)

Mass spectrometric value (ESI-MS) 578 (M−1)

Compound 300 4-({3-[Bis-(2-hydroxy-ethyl)-amino]-propylamino}-methyl)-N-[4-bromo-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 300 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 1.73 (2H, m), 2.29 (3H, s), 2.30 (3H, s), 2.61 (6H, m), 2.73 (2H, t, J=6.8 Hz), 3.60 (4H, m), 3.89 (2H, s), 7.18 (1H, d, J=7.6 Hz), 7.53 (3H, m), 7.64 (1H, s), 7.71 (1H, dd, J=8.8 Hz, J=2.4 Hz), 7.98-8.05 (3H, m), 8.29 (1H, s), 8.60 (1H, d, J=9.0 Hz)

Mass spectrometric value (ESI-MS) 626 (M+1)

Compound 301 4-({3-[Bis-(2-hydroxy-ethyl)-amino]-propylamino}-methyl)-N-[4-bromo-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 301 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 1.74 (2H, m), 2.63 (6H, m), 2.75 (2H, m), 3.61 (4H, m), 3.90 (2H, s), 7.17 (1H, m), 7.45 (1H, m), 7.33-7.72 (5H, m), 7.89 (2H, m), 8.09 (1H, d, J=2.4 Hz), 8.35 (1H, s), 8.60 (1H, d, J=8.8 Hz)

Mass spectrometric value (ESI-MS) 612 (M−1)

Compound 302 4-({3-[Bis-(2-hydroxy-ethyl)-amino]-propylamino}-methyl)-N-[4-bromo-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 302 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 1.75 (2H, m), 2.63 (6H, m), 2.78 (2H, m), 3.61 (4H, m), 3.91 (2H, s), 7.54 (2H, d, J=8.0 Hz), 7.66 (2H, m), 8.00 (3H, m), 8.11 (1H, d, J=2.4 Hz), 8.32 (1H, s), 8.38 (1H, s), 8.58 (1H, d, J=8.8 Hz)

Mass spectrometric value (ESI-MS) 696 (M−1)

Compound 303 4-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[4-bromo-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 303 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 1.11 (3H, s), 1.13 (3H, s), 2.29 (6H, m), 2.45-2.65 (4H, m), 3.60-3.99 (4H, m), 7.18 (1H, d, J=7.8 Hz), 7.47 (3H, m), 7.55 (1H, m), 7.64 (1H, s), 7.70 (1H, s), 8.01 (2H, d, J=7.6 Hz), 8.31 (1H, s), 8.52 (1H, d, J=8.6 Hz)

Mass spectrometric value (ESI-MS) 595 (M−1)

Compound 304 4-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[4-bromo-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 304 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 1.11 (6H, m), 2.34 (3H, s), 2.42-2.62 (4H, m), 3.59-3.93 (4H, m), 7.19 (2H, d, J=8.0 Hz), 7.44 (3H, m), 7.68 (3H, m), 7.98 (2H, d, J=7.8 Hz), 8.41 (2H, m)

Mass spectrometric value (ESI-MS) 579 (M−1)

Compound 305 N-[4-Bromo-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-[4-(2-morpholin-4-yl-2-oxo-ethyl)-piperazin-1-ylmethyl]-benzamide

The title compound 305 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 2.26 (3H, s), 2.28 (3H, s), 2.49 (8H, m), 3.16 (2H, s), 3.49-3.70 (10H, m), 7.15 (1H, d, J=7.8 Hz), 7.40-7.52 (4H, m), 7.62 (1H, s), 7.73 (1H, s), 7.96 (2H, d, J=7.8 Hz), 8.38 (1H, s), 8.49 (1H, d, J=8.8 Hz)

Mass spectrometric value (ESI-MS) 673 (M−1)

Compound 306 N-[4-Bromo-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-[4-(2-morpholin-4-yl-2-oxo-ethyl)-piperazin-1-ylmethyl]-benzamide

The title compound 306 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 2.50 (8H, m), 3.15 (2H, s), 3.49-3.75 (10H, m), 7.42 (2H, m), 7.54 (2H, m), 7.71 (1H, s), 7.99 (4H, m), 8.44 (1H, d, J=8.5 Hz), 8.51 (1H, s)

Mass spectrometric value (ESI-MS) 747 (M−1)

Compound 307 N-[4-Bromo-2-(4-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-4-[4-(2-morpholin-4-yl-2-oxo-ethyl)-piperazin-1-ylmethyl]-benzamide

The title compound 307 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 2.48 (8H, m), 3.16 (2H, s), 3.48-3.75 (10H, m), 3.81 (3H, s), 6.89 (2H, d, J=8.8 Hz), 7.39 (2H, d, J=8.1 Hz), 7.50 (1H, m), 7.69-7.53 (3H, m), 7.96 (2H, d, J=8.0 Hz), 8.40 (1H, s), 8.49 (1H, d, J=9.0 Hz)

Mass spectrometric value (ESI-MS) 675 (M−1)

Compound 308 4-[1,4′]Bipiperidinyl-1′-ylmethyl-N-[4-bromo-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 308 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 1.47 (2H, m), 1.65 (6H, m), 1.82 (2H, m), 1.94 (2H, t, J=11.2 Hz), 2.24 (3H, s), 2.26 (3H, s), 2.55-2.68 (5H, m), 2.87 (2H, d, J=11.5 Hz), 3.47 (2H, s), 7.13 (1H, d, J=7.8 Hz), 7.36 (2H, d, J=8.0 Hz), 7.43 (1H, d, J=7.8 Hz), 7.50 (1H, d, J=8.8 Hz), 7.59 (1H, s), 7.88 (1H, s), 7.96 (2H, d, J=8.0 Hz), 8.43 (1H, s), 8.53 (1H, d, J=9.0 Hz)

Mass spectrometric value (ESI-MS) 630 (M−1)

Compound 309 4-[1,4′]Bipiperidinyl-1′-ylmethyl-N-[4-bromo-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 309 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 1.47 (2H, m), 1.59-1.73 (6H, m), 1.82 (2H, m), 1.93 (2H, m), 2.34 (3H, s), 2.57-2.69 (5H, m), 2.87 (2H, d, J=11.5 Hz), 3.47 (2H, s), 7.19 (2H, d, J=8.0 Hz), 7.36 (2H, d, J=8.0 Hz), 7.51 (1H, m), 7.66 (2H, d, J=8.0 Hz), 7.87 (1H, s), 7.96 (2H, d, J=8.0 Hz), 8.45 (1H, s), 8.53 (1H, d, J=9.0 Hz)

Mass spectrometric value (ESI-MS) 614 (M−1)

Compound 310 4-[1,4′]Bipiperidinyl-1′-ylmethyl-N-[4-bromo-2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 310 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 1.47 (2H, m), 1.59-1.74 (6H, m), 1.83 (2H, m), 1.94 (2H, m), 2.35 (3H, s), 2.59-2.75 (5H, m), 2.87 (2H, d, J=11.5 Hz), 3.47 (2H, s), 7.19 (1H, d, J=7.6 Hz), 7.26 (1H, m), 7.36 (2H, d, J=8.1 Hz), 7.51 (2H, m), 7.64 (1H, s), 7.90 (1H, s), 7.95 (2H, d, J=8.1 Hz), 8.46 (1H, s), 8.54 (1H, d, J=8.8 Hz)

Mass spectrometric value (ESI-MS) 614 (M−1)

Compound 311 4-[1,4′]Bipiperidinyl-1′-ylmethyl-N-[4-bromo-2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 311 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 1.47 (2H, m), 1.60-1.75 (6H, m), 1.83 (2H, m), 1.93 (2H, m), 2.56-2.74 (5H, m), 2.87 (2H, d, J=11.2 Hz), 3.47 (2H, s), 7.06 (2H, t, J=8.5 Hz), 7.36 (2H, d, J=8.1 Hz), 7.50 (1H, d, J=8.3 Hz), 7.74 (2H, m), 7.87-8.00 (3H, m), 8.50 (2H, m)

Mass spectrometric value (ESI-MS) 620 (M−1)

Compound 312 4-[1,4′]Bipiperidinyl-1′-ylmethyl-N-[4-bromo-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 312 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 1.47 (2H, m), 1.59-1.75 (6H, m), 1.83 (2H, m), 1.94 (2H, m), 2.50-2.70 (5H, m), 2.87 (2H, d, J=11.2 Hz), 3.48 (2H, s), 7.08 (1H, m), 7.30-7.40 (3H, m), 7.50 (3H, m), 7.87 (1H, s), 7.95 (2H, d, J=8.1 Hz), 8.49 (2H, m)

Mass spectrometric value (ESI-MS) 620 (M−1)

Compound 313 4-[1,4′]Bipiperidinyl-1′-ylmethyl-N-[4-bromo-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 313 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 1.50 (2H, m), 1.60-1.80 (6H, m), 1.82-1.96 (4H, m), 2.62-2.78 (5H, m), 2.86 (2H, d, J=11.0 Hz), 3.46 (2H, s), 7.35 (2H, d, J=8.0 Hz), 7.51 (2H, d, J=8.6 Hz), 7.94 (5H, m), 8.50 (1H, d, J=9.0 Hz), 8.57 (1H, s)

Mass spectrometric value (ESI-MS) 702 (M−1)

Compound 314 4-[1,4′]Bipiperidinyl-1′-ylmethyl-N-[4-bromo-2-(4-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 314 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 1.47 (2H, m), 1.59-1.75 (6H, m), 1.83 (2H, m), 1.94 (2H, m), 2.60-2.76 (5H, m), 2.87 (2H, d, J=11.5 Hz), 3.46 (2H, s), 3.79 (3H, s), 6.88 (2H, d, J=8.6 Hz), 7.35 (2H, d, J=8.0 Hz), 7.52 (1H, d, J=9.0 Hz), 7.68 (2H, d, J=8.6 Hz), 7.90 (1H, s), 7.95 (2H, d, J=8.0 Hz), 8.41 (1H, s), 8.55 (1H, d, J=9.0 Hz)

Mass spectrometric value (ESI-MS) 632 (M−1)

Compound 315 4-[1,4′]Bipiperidinyl-1′-ylmethyl-N-[4-bromo-2-(3-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 315 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 1.47 (2H, m), 1.58-1.80 (6H, m), 1.83 (2H, m), 1.92 (2H, m), 2.59-2.75 (5H, m), 2.85 (2H, m), 3.45 (2H, s), 3.82 (3H, s), 6.91 (1H, d, J=6.8 Hz), 7.20-7.40 (5H, m), 7.52 (1H, d, J=9.0 Hz), 7.94 (3H, m), 8.49 (1H, s), 8.56 (1H, d, J=9.0 Hz)

Mass spectrometric value (ESI-MS) 632 (M−1)

Compound 316 N-[4-Bromo-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-[4-(2-hydroxy-ethyl)-piperazin-1-ylmethyl]-benzamide

The title compound 316 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 2.29 (3H, s), 2.30 (3H, s), 2.48-2.65 (10H, m), 3.58 (2H, s), 3.64 (2H, t, J=5.2 Hz), 7.18 (1H, d, J=7.8 Hz), 7.46 (3H, m), 7.57 (1H, d, J=9.0 Hz), 7.64 (1H, s), 7.70 (1H, s), 7.98 (2H, d, J=7.8 Hz), 8.29 (1H, s), 8.56 (1H, d, J=9.0 Hz)

Mass spectrometric value (ESI-MS) 592 (M−1)

Compound 317 N-[4-Bromo-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-[4-(2-hydroxy-ethyl)-piperazin-1-ylmethyl]-benzamide

The title compound 317 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 2.40 (3H, s), 2.54-2.75 (10H, m), 3.60 (2H, s), 3.68 (2H, m), 7.25 (2H, m), 7.45 (2H, d, J=8.0 Hz), 7.62 (1H, m), 7.70 (3H, m), 7.98 (2H, d, J=8.0 Hz), 8.28 (1H, s), 8.64 (1H, d, J=9.0 Hz)

Mass spectrometric value (ESI-MS) 576 (M−1)

Compound 318 N-[4-Bromo-2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-[4-(2-hydroxy-ethyl)-piperazin-1-ylmethyl]-benzamide

The title compound 318 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 2.40 (3H, s), 2.50-2.67 (10H, m), 3.58 (2H, s), 3.64 (2H, t, J=5.3 Hz), 7.24 (1H, m), 7.32 (1H, m), 7.45 (2H, d, J=8.0 Hz), 7.56 (2H, m), 7.70 (2H, m), 7.99 (2H, d, J=8.0 Hz), 8.34 (1H, s), 8.53 (1H, d, J=9.2 Hz)

Mass spectrometric value (ESI-MS) 578 (M−1)

Compound 319 N-[4-Bromo-2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-4-[4-(2-hydroxy-ethyl)-piperazin-1-ylmethyl]-benzamide

The title compound 319 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 2.48-2.70 (10H, m), 3.58 (2H, s), 3.65 (2H, t, J=5.2 Hz), 7.12 (2H, m), 7.45 (2H, d, J=8.0 Hz), 7.53 (1H, m), 7.68 (1H, s), 7.82 (2H, m), 7.98 (2H, d, J=8.0 Hz), 8.40 (1H, s), 8.46 (1H, d, J=8.8 Hz)

Mass spectrometric value (ESI-MS) 580 (M−1)

Compound 320 N-[4-Bromo-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-4-[4-(2-hydroxy-ethyl)-piperazin-1-ylmethyl]-benzamide

The title compound 320 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 2.50-2.75 (10H, m), 3.60 (2H, s), 3.69 (2H, t, J=5.2 Hz), 7.14 (1H, m), 7.36-7.72 (7H, m), 7.98 (2H, d, J=8.0 Hz), 8.39 (1H, s), 8.50 (1H, d, J=9.0 Hz)

Mass spectrometric value (ESI-MS) 582 (M−1)

Compound 321 N-[4-Bromo-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-[4-(2-hydroxy-ethyl)-piperazin-1-ylmethyl]-benzamide

The title compound 321 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 2.50-2.72 (10H, m), 3.60 (2H, s), 3.66 (2H, t, J=5.2 Hz), 7.15 (1H, m), 7.43-7.72 (6H, m), 7.99 (2H, d, J=8.0 Hz), 8.07 (1H, s), 8.46 (1H, m)

Mass spectrometric value (ESI-MS) 664 (M−1)

Compound 322 N-[4-Bromo-2-(4-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-4-[4-(2-hydroxy-ethyl)-piperazin-1-ylmethyl]-benzamide

The title compound 322 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 2.50-2.70 (10H, m), 3.58 (2H, s), 3.65 (2H, t, J=5.2 Hz), 3.85 (3H, s), 6.94 (2H, d, J=8.8 Hz), 7.44 (2H, d, J=8.3 Hz), 7.59 (1H, m), 7.69-7.80 (3H, m), 7.98 (2H, d, J=7, 8 Hz), 8.28 (1H, s), 8.60 (1H, d, J=9.0 Hz)

Mass spectrometric value (ESI-MS) 594 (M−1)

Compound 323 N-[4-Bromo-2-(3-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-4-[4-(2-hydroxy-ethyl)-piperazin-1-ylmethyl]-benzamide

The title compound 323 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 2.45-2.65 (10H, m), 3.57 (2H, s), 3.63 (2H, t, J=5.4 Hz), 3.86 (3H, s), 6.98 (1H, m), 7.17 (1H, m), 7.22-7.58 (5H, m), 7.71 (1H, s), 7.97 (2H, d, J=7.8 Hz), 8.38 (1H, s), 8.50 (1H, d, J=8.8 Hz)

Mass spectrometric value (ESI-MS) 592 (M−1)

Compound 324 N-[4-Bromo-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-(4-hydroxy-piperidin-1-ylmethyl)-benzamide

The title compound 324 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 1.61 (2H, m), 1.86-2.24 (4H, m), 2.89 (3H, s), 2.30 (3H, s), 2.75 (2H, m), 3.57 (2H, s), 3.71 (1H, m), 7.18 (1H, d, J=7.8 Hz), 7.45 (3H, m), 7.55 (1H, m), 7.64 (1H, s), 7.69 (1H, s), 7.98 (2H, d, J=7.6 Hz), 8.30 (1H, s), 8.54 (1H, d, J=9.0 Hz)

Mass spectrometric value (ESI-MS) 563 (M−1)

Compound 325 N-[4-Bromo-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-(4-hydroxy-piperidin-1-ylmethyl)-benzamide

The title compound 325 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 1.60 (2H, m), 1.89 (2H, m), 2.17 (2H, m), 2.39 (3H, s), 2.74 (2H, m), 3.56 (2H, m), 3.71 (1H, s), 7.15-7.27 (2H, m), 7.44 (2H, d, J=8.0 Hz), 7.56 (1H, m), 7.69 (3H, m), 7.98 (2H, d, J=8.0 Hz), 8.32 (1H, s), 8.55 (1H, d, J=9.0 Hz)

Mass spectrometric value (ESI-MS) 549 (M−1)

Compound 326 N-[4-Bromo-2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-(4-hydroxy-piperidin-1-ylmethyl)-benzamide

The title compound 326 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 1.60 (2H, m), 1.90 (2H, m), 2.17 (2H, m), 2.40 (3H, s), 2.74 (2H, m), 3.56 (2H, m), 3.71 (1H, m), 7.24-7.34 (2H, m), 7.45 (2H, m), 7.58 (2H, m), 7.70 (2H, m), 7.98 (2H, d, J=7.8 Hz), 8.31 (1H, s), 8.57 (1H, d, J=9.0 Hz)

Mass spectrometric value (ESI-MS) 547 (M−1)

Compound 327 N-[4-Bromo-2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-4-(4-hydroxy-piperidin-1-ylmethyl)-benzamide

The title compound 327 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 1.59 (2H, m), 1.89 (2H, m), 2.17 (2H, m), 2.74 (2H, m), 3.56 (2H, s), 3.72 (1H, m), 7.13 (2H, m), 7.45 (2H, d, J=8.0 Hz), 7.56 (1H, m), 7.66 (1H, s), 7.82 (2H, m), 7.98 (2H, d, J=8.0 Hz), 8.36 (1H, s), 8.51 (1H, d, J=8.0 Hz)

Mass spectrometric value (ESI-MS) 551 (M−1)

Compound 328 N-[4-Bromo-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-4-(4-hydroxy-piperidin-1-ylmethyl)-benzamide

The title compound 328 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 1.65 (2H, m), 1.93 (2H, m), 2.30 (2H, m), 2.80 (2H, m), 3.65 (2H, s), 3.75 (1H, m), 7.15 (1H, m), 7.26-7.69 (7H, m), 7.99 (2H, d, J=7.8 Hz), 8.35 (1H, s), 8.54 (1H, d, J=9.0 Hz)

Mass spectrometric value (ESI-MS) 551 (M−1)

Compound 329 N-[4-Bromo-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-(4-hydroxy-piperidin-1-ylmethyl)-benzamide

The title compound 329 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 1.58 (2H, m), 1.91 (2H, m), 2.38 (2H, m), 2.75 (2H, m), 3.58 (2H, s), 3.71 (1H, m), 7.16 (1H, m), 7.47 (2H, d, J=8.1 Hz), 7.52-7.75 (4H, m), 7.98 (2H, d, J=8.1 Hz), 8.24 (1H, s), 8.58 (1H, m)

Mass spectrometric value (ESI-MS) 635 (M−1)

Compound 330 N-[4-Bromo-2-(4-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-4-(4-hydroxy-piperidin-1-ylmethyl)-benzamide

The title compound 330 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 1.62 (2H, m), 1.90 (2H, m), 2.20 (2H, m), 2.75 (2H, m), 3.59 (2H, s), 3.72 (1H, m), 3.86 (3H, s), 6.95 (2H, d, J=8.8 Hz), 7.45 (2H, d, J=8.0 Hz), 7.62-7.80 (4H, m), 7.98 (2H, m), 8.21 (1H, s), 8.70 (1H, m)

Mass spectrometric value (ESI-MS) 565 (M−1)

Compound 331 N-[4-Bromo-2-(3-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-4-(4-hydroxy-piperidin-1-ylmethyl)-benzamide

The title compound 331 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 1.60 (2H, m), 1.90 (2H, m), 2.17 (2H, m), 2.75 (2H, m), 2.57 (2H, s), 2.72 (1H, m), 3.87 (3H, s), 6.99 (1H, m), 7.25-7.77 (7H, m), 7.97 (2H, d, J=7.5 Hz), 8.30 (1H, s), 8.63 (1H, d, J=8.6 Hz)

Mass spectrometric value (ESI-MS) 563 (M−1)

Compound 332 N-[4-Bromo-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-(4-hydroxymethyl-piperidin-1-ylmethyl)-benzamide

The title compound 332 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 1.25-1.76 (5H, m), 2.03 (2H, m), 2.28 (3H, s), 2.29 (3H, s), 2.91 (2H, m), 3.50 (2H, d, J=6.3 Hz), 3.58 (2H, s), 7.17 (1H, m), 7.41-7.72 (6H, m), 7.98 (2H, d, J=8.0 Hz), 8.32 (1H, s), 8.53 (1H, d, J=8.5 Hz)

Mass spectrometric value (ESI-MS) 575 (M−1)

Compound 333 N-[4-Bromo-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-(4-hydroxymethyl-piperidin-1-ylmethyl)-benzamide

The title compound 333 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 1.20-1.76 (5H, m), 2.04 (2H, m), 2.39 (3H, s), 2.93 (2H, m), 3.50 (2H, d, J=6.4 Hz), 3.60 (2H, s), 7.24 (2H, m), 7.42-7.76 (6H, m), 7.98 (2H, d, J=7.8 Hz), 8.33 (1H, s), 8.58 (1H, d, J=8.8 Hz)

Mass spectrometric value (ESI-MS) 561 (M−1)

Compound 334 N-[4-Bromo-2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-(4-hydroxymethyl-piperidin-1-ylmethyl)-benzamide

The title compound 334 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 1.20-2.15 (7H, m), 2.38 (3H, s), 2.93 (2H, m), 3.40-3.65 (4H, m), 7.20-7.32 (1H, m), 7.40-7.70 (6H, m), 8.27 (1H, s), 8.65 (1H, d, J=8.8 Hz)

Mass spectrometric value (ESI-MS) 563 (M−1)

Compound 335 N-[4-Bromo-2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-4-(4-hydroxymethyl-piperidin-1-ylmethyl)-benzamide

The title compound 335 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 1.20-1.40 (5H, m), 1.72 (2H, m), 2.93 (2H, m), 3.47-3.65 (4H, m), 7.12 (2H, m), 7.40-7.88 (6H, m), 7.98 (2H, d, J=8.5 Hz), 8.47 (1H, s), 8.54 (1H, d, J=8.8 Hz)

Mass spectrometric value (ESI-MS) 567 (M−1)

Compound 336 N-[4-Bromo-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-4-(4-hydroxymethyl-piperidin-1-ylmethyl)-benzamide

The title compound 336 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 1.20-1.80 (5H, m), 2.05 (2H, m), 2.93 (2H, m), 3.42-3.65 (4H, m), 7.12 (1H, m), 7.24-7.66 (6H, m), 7.82 (1H, s), 7.97 (2H, d, J=8.3 Hz), 8.30 (1H, s), 8.64 (1H, d, J=9.0 Hz)

Mass spectrometric value (ESI-MS) 565 (M−1)

Compound 337 N-[4-Bromo-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-(4-hydroxymethyl-piperidin-1-ylmethyl)-benzamide

The title compound 337 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 1.20-2.22 (7H, m), 2.92 (2H, m), 3.39-3.65 (4H, m), 7.14-8.10 (9H, m), 8.32 (1H, s), 8.64 (1H, d, J=8.8 Hz)

Mass spectrometric value (ESI-MS) 649 (M−1)

Compound 338 N-[4-Bromo-2-(4-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-4-(4-hydroxymethyl-piperidin-1-ylmethyl)-benzamide

The title compound 338 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 1.20-1.76 (5H, m), 2.03 (2H, m), 2.91 (2H, m), 3.46-3.64 (4H, m), 3.84 (3H, s), 6.93 (2H, m), 7.41-7.80 (6H, m), 7.97 (2H, d, J=7.8 Hz), 8.32 (1H, s), 8.55 (1H, d, J=9.0 Hz)

Mass spectrometric value (ESI-MS) 579 (M−1)

Compound 339 N-[4-Bromo-2-(3-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-4-(4-hydroxymethyl-piperidin-1-ylmethyl)-benzamide

The title compound 339 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 1.20-2.25 (7H, m), 2.95 (2H, m), 3.45-3.67 (4H, m), 3.87 (3H, s), 6.80-7.80 (8H, m), 7.95 (2H, m), 8.25 (1H, s), 8.65 (1H, m)

Mass spectrometric value (ESI-MS) 577 (M−1)

Compound 340 N-[4-Bromo-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-[4-(2-hydroxy-ethyl)-piperidin-1-ylmethyl]-benzamide

The title compound 340 was produced in the same manner as in Example 5.

¹H-NMR (DMSO-d₆, 400 MHz): δ 1.15 (2H, m), 1.35 (3H, m), 1.61 (2H, m), 1.92 (2H, m), 2.27 (3H, s), 2.29 (3H, s), 2.77 (2H, m), 3.42 (2H, m), 3.52 (2H, s), 7.24 (1H, d, J=7.8 Hz), 7.48 (3H, m), 7.55 (1H, s), 7.80 (1H, dd, J=9.0 Hz, J=2.4 Hz), 7.88 (2H, d, J=8.0 Hz), 8.09 (1H, d, J=2.4 Hz), 8.38 (1H, s), 8.52 (1H, d, J=9.0 Hz)

Mass spectrometric value (ESI-MS) 589 (M−1)

Example 6

Compound 341 N-[4-Bromo-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-3-(1H-[1,2,4]triazole-3-sulfinylmethyl)-benzamide

Compound 271: N-[4-bromo-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-3-(1H-[1,2,4]triazol-3-ylsulfanylmethyl)-benzamide (100 mg) produced in the same manner as in Example 5 was dissolved in methylene chloride (5 ml), 3-chloro-peroxybenzoic acid (32 mg) was added to the solution, and the mixture was stirred at room temperature for 2 hr. The resultant crystals were filtered and were washed with methylene chloride and hexane to give the title compound 341 (76 mg, yield 70%).

¹H-NMR (DMSO-d₆, 400 MHz): δ 4.65 (2H, m), 7.29 (1H, m), 7.53 (4H, m), 7.83 (3H, m), 8.08 (1H, d, J=2.0 Hz), 8.43 (2H, m), 8.83 (1H, s), 11.72 (1H, s)

Mass spectrometric value (ESI-MS) 569 (M−1)

Compound 342 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-3-yl]-benzamide

The title compound 342 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 1.07 (6H, m), 2.30 (12H, m), 2.56 (8H, m), 3.61 (2H, s), 7.18 (1H, d, J=7.6 Hz), 7.30-7.60 (6H, m), 7.93 (1H, d, J=7.6 Hz), 8.01 (1H, s)

Mass spectrometric value (ESI-MS) 532 (M−1)

Compound 343 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[4-methyl-2-(4-methyl-benzylidene-hydrazinocarbonyl)-thiophen-3-yl]-benzamide

The title compound 343 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 1.05 (6H, t, J=7.1 Hz), 2.26 (3H, s), 2.31 (3H, s), 2.39 (3H, s), 2.51-2.80 (8H, m), 3.60 (2H, s), 7.21 (2H, d, J=7.6 Hz), 7.30-7.80 (6H, m), 7.93 (1H, d, J=7.6 Hz), 8.00 (1H, s)

Mass spectrometric value (ESI-MS) 518 (M−1)

Compound 344 N-[2-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-3-yl]-3-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 344 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 1.03 (6H, t, J=7.2 Hz), 2.25 (3H, s), 2.27 (3H, s), 2.52-2.70 (8H, m), 3.60 (2H, s), 7.35-7.60 (5H, m), 7.80 (1H, m), 7.92 (1H, d, J=7.6 Hz), 8.00 (2H, d, J=3.9 Hz)

Mass spectrometric value (ESI-MS) 606 (M−1)

Compound 345 3-[1,4′]Bipiperidinyl-1′-ylmethyl-N-[2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-3-yl]-benzamide

The title compound 345 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 1.44 (2H, m), 1.50-2.10 (12H, m), 2.30 (10H, m), 2.57 (2H, m), 2.96 (2H, d, J=11.7 Hz), 3.56 (2H, s), 7.17 (1H, d, J=7.6 Hz), 7.30-7.55 (6H, m), 7.92 (1H, d, J=7.6 Hz), 7.99 (1H, s)

Mass spectrometric value (ESI-MS) 570 (M−1)

Compound 346 N-[4-Bromo-2-(3-phenyl-allylidene-hydrazinocarbonyl)-phenyl]-nicotinamide

The title compound 346 was produced in the same manner as in Example 1.

¹H-NMR (CD₃OD, 400 MHz): δ 9.15 (1H, s), 8.73-8.78 (1H, m), 8.54 (1H, d, J=8.8 Hz), 8.26-8.42 (1H, m), 8.17 (1H, d, J=6.6 Hz), 8.06 (1H, d, J=2.2 Hz), 7.77 (1H, dd, J=8.8 Hz, J=2.2 Hz), 7.55-7.64 (3H, m), 7.30-7.42 (3H, m), 7.05-7.10 (2H, m)

Mass spectrometric value (ESI-MS) 447 (M−1)

Compound 347 N-[4-Bromo-2-(3-phenyl-allylidene-hydrazinocarbonyl)-phenyl]-isonicotinamide

The title compound 347 was produced in the same manner as in Example 1.

¹H-NMR (CD₃OD, 400 MHz): δ 8.75-8.00 (2H, m), 8.57 (1H, d, J=9.0 Hz), 8.28 (1H, d, J=7.3 Hz), 8.05-8.08 (1H, m), 7.92-7.95 (2H, m), 7.78 (1H, dd, J=2.4 Hz, J=9.0 Hz), 7.57 (2H, d, J=7.8 Hz), 7.30-7.42 (3, m), 7.05-7.10 (2H, m)

Mass spectrometric value (ESI-MS) 447 (M−1)

Compound 348 N-[4-Chloro-2-(3-phenyl-allylidene-hydrazinocarbonyl)-phenyl]-nicotinamide

The title compound 348 was produced in the same manner as in Example 1.

¹H-NMR (CD₃OD, 400 MHz): δ 9.14-9.18 (1H, m), 8.75 (1H, dd, J=4.9 Hz, J=1.5 Hz), 8.59 (1H, d, J=8.8 Hz), 8.39 (1H, ddd, J=1.4 Hz, J=1.4 Hz, J=8.0 Hz), 8.17 (1H, d. J=6.8 Hz), 7.92 (1H, d, J=2.4 Hz), 7.55-7.65 (4H, m), 7.30-7.42 (3H, m), 7.05-7.10 (2H, m)

Mass spectrometric value (ESI-MS) 403 (M−1)

Compound 349 N-[4-Chloro-2-(3-phenyl-allylidene-hydrazinocarbonyl)-phenyl]-isonicotinamide

The title compound 349 was produced in the same manner as in Example 1.

¹H-NMR (CD₃OD, 400 MHz): δ 8.78 (2H, dd, J=1.7 Hz, J=4.4 Hz), 8.62 (1H, d, J=9.0 Hz), 8.18 (1H, dd, J=1.4 Hz, J=7.6 Hz), 7.93-7.97 (3H, m), 7.64 (1H, dd, J=2.2 Hz, J=9.0 Hz), 7.55-7.60 (2H, m), 7.31-7.43 (3H, m), 7.06-7.12 (2H, m)

Mass spectrometric value (ESI-MS) 403 (M−1)

Compound 350 N-{4-Bromo-2-[3-(2-hydroxy-ethoxy)-benzylidene-hydrazinocarbonyl]-phenyl}-isonicotinamide

The title compound 350 was produced in the same manner as in Example 1.

¹H-NMR (CD₃OD, 400 MHz): δ 8.78 (2H, dd, J=1.7 Hz, J=4.4 Hz), 8.57 (1H, d, J=8.8 Hz), 8.31 (1H, s), 8.08 (1H, d, J=2.2 Hz), 7.95 (2H, dd, J=1.7 Hz, J=4.6 Hz), 7.81 (1H, s), 7.77-7.79 (1H, m), 7.76 (1H, d, J=2.2 Hz), 7.03 (2H, d, J=8.8 Hz), 4.11 (2H, t, J=9.5 Hz), 3.89 (2H, t, J=9.3 Hz)

Mass spectrometric value (ESI-MS) 481 (M−1)

Compound 351 N-{4-Chloro-2-[3-(2-hydroxy-ethoxy)-benzylidene-hydrazinocarbonyl]-phenyl}-isonicotinamide

The title compound 351 was produced in the same manner as in Example 1.

¹H-NMR (CD₃OD, 400 MHz): δ 8.78 (2H, dd, J=1.7 Hz, J=4.6 Hz), 8.63 (1H, d, J=9.0 Hz), 8.31 (1H, s), 7.93-7.97 (3H, m), 7.79 (2H, d, J=8.8 Hz), 7.64 (1H, dd, J=2.4 Hz, J=9.0 Hz), 7.03 (2H, d, J=8.8 Hz), 4.11 (2H, t, J=4.8 Hz), 3.89 (2H, t, J=4.8 Hz)

Mass spectrometric value (ESI-MS) 437 (M−1)

Compound 352 N-{4-Bromo-2-[3-(2-methoxy-phenyl)-allylidene-hydrazinocarbonyl]-phenyl}-nicotinamide

The title compound 352 was produced in the same manner as in Example 1.

¹H-NMR (CD₃OD, 400 MHz): δ 9.15 (1H, d, J=2.2 Hz), 8.75 (1H, dd, J=1.4 Hz, J=4.9 Hz), 8.39 (1H, ddd, J=1.8 Hz, J=1.8 Hz, J=7.8 Hz), 8.16 (1H, d, J=9.2 Hz), 8.06 (1H, d, J=2.4 Hz), 7.77 (1H, dd, J=2.4 Hz, J=9.0 Hz), 7.56-7.65 (2H, m), 7.30-7.40 (2H, m), 7.11 (1H, dd, J=9.5 Hz, J=6.1 Hz), 7.02 (1H, d, J=8.3 Hz), 6.97 (1H, dd, J=7.7 Hz), 3.90 (3H, s)

Mass spectrometric value (ESI-MS) 479, 480 (M−1)

Compound 353 N-{4-Bromo-2-[3-(2-methoxy-phenyl)-allylidene-hydrazinocarbonyl]-phenyl}-isonicotinamide

The title compound 353 was produced in the same manner as in Example 1.

¹H-NMR (CD₃OD, 400 MHz): δ 8.76-8.80 (2H, m), 8.57 (1H, d, J=8.8 Hz), 8.17 (1H, d, J=9.5 Hz), 8.07 (1H, d, J=2.4 Hz), 7.94 (2H, dd, J=1.7 Hz, J=4.4 Hz), 7.78 (1H, dd, J=2.4 Hz, J=8.9 Hz), 7.59 (1H, d, J=6.4 Hz), 7.30-7.41 (2H, m), 6.95-7.24 (3H, m), 3.90 (3H, s)

Mass spectrometric value (ESI-MS) 479, 480 (M−1)

Compound 354 N-{4-Chloro-2-[3-(2-methoxy-phenyl)-allylidene-hydrazinocarbonyl]-phenyl}-nicotinamide

The title compound 354 was produced in the same manner as in Example 1.

¹H-NMR (CD₃OD, 400 MHz): δ 9.16 (1H, d, J=2.4 Hz), 8.76 (1H, dd, J=2.1 Hz, J=5.3 Hz), 8.60 (1H, d, J=9.0 Hz), 8.35-8.42 (1H, m), 8.16 (1H, d, J=9.5 Hz), 7.92 (1H, d, J=2.4 Hz), 7.58-7.65 (3H, m), 7.30-7.41 (2H, m), 7.11 (1H, dd, J=9.5 Hz, J=16.1 Hz), 7.02 (1H, d, J=7.8 Hz), 6.97 (1H, dd, J=7.6 Hz, J=7.6 Hz), 3.90 (3H, s)

Mass spectrometric value (ESI-MS) 433 (M−1)

Compound 355 N-{4-Chloro-2-[3-(2-methoxy-phenyl)-allylidene-hydrazinocarbonyl]-phenyl}-isonicotinamide

The title compound 355 was produced in the same manner as in Example 1.

¹H-NMR (CD₃OD, 400 MHz): δ 8.78 (2H, d, J=4.4 Hz), 8.63 (1H, d, J=8.8 Hz), 8.17 (1H, d, J=9.3 Hz), 7.92-7.98 (3H, m), 7.55-7.70 (2H, m), 7.30-7.38 (2H, m), 7.07-7.17 (1H, m), 6.95-7.05 (2H, m)

Mass spectrometric value (ESI-MS) 435 (M−1)

Compound 356 Pridin-2-carboxylic acid [4-bromo-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-amide hydrochloride

The title compound 356 was produced in the same manner as in Example 3.

Mass spectrometric value (ESI-MS) 473 (M−1)

Compound 357 N-[4-Bromo-2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-(3-fluoro-phenylsulfanylmethyl)-benzamide

The title compound 357 was produced in the same manner as in Example 4.

¹H-NMR (CD₃OD, 400 MHz): δ 8.59 (1H, d, J=8.8 Hz), 8.33 (1H, s), 8.05-8.08 (1H, m), 7.93 (2H, d, J=8.6 Hz), 7.60-7.80 (4H, m), 7.51 (2H, d, J=8.6 Hz), 6.80-7.40 (5H, m), 4.27 (2H, s), 2.40 (3H, s)

Mass spectrometric value (ESI-MS) 574 (M−1)

Compound 358 N-{2-[3-(4-Dimethylamino-phenyl)-allylidene-hydrazinocarbonyl]-phenyl}-nicotinamide

The title compound 358 was produced in the same manner as in Example 1.

¹H-NMR (CD₃OD, 400 MHz): δ 9.17 (1H, s, J=1.5 Hz), 8.75 (1H, dd, J=1.5 Hz, H=4.9 Hz), 8.60 (1H, d, J=8.3 Hz), 8.38-8.44 (1H, m), 8.11 (1H, d, J=9.0 Hz), 7.85 (1H, d, J=7.8 Hz), 7.60-7.65 (2H, m), 7.42 (2H, d, J=8.8 Hz), 7.29 (1H, dd, J=7.7 Hz, J=7.7 Hz), 6.94-7.00 (1H, m), 6.80-6.88 (1H, m), 6.74 (2H, d, J=9.0 Hz), 3.00 (6H, s)

Mass spectrometric value (ESI-MS) 412 (M−1)

Compound 359 Pyridin-2-carboxylic acid [4-chloro-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-amide

The title compound 359 was produced in the same manner as in Example 1.

¹H-NMR (CD₃OD, 400 MHz): δ 8.79 (1H, d, J=9.0 Hz), 8.73 (1H, d, J=5.1 Hz), 8.33 (1H, s), 8.22 (1H, d, J=7.8 Hz), 7.98-8.04 (1H, m), 7.89 (1H, d, J=2.4 Hz), 7.73 (1H, d, J=10.0 Hz), 7.58-7.66 (3H, m), 7.42-7.50 (1H, m), 7.15-7.22 (1H, m)

Mass spectrometric value (ESI-MS) 395 (M−1)

Compound 360 Pyridin-2-carboxylic acid [4-chloro-2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-amide

The title compound 360 was produced in the same manner as in Example 1.

¹H-NMR (CD₃OD, 400 MHz): δ 8.78 (1H, d, J=8.8 Hz), 8.72 (1H, d, J=4.9 Hz), 8.33 (1H, s), 8.22 (1H, d, J=7.8 Hz), 8.01 (1H, ddd, J=7.8 Hz, J=7.8 Hz, J=1.4 Hz), 7.89-7.95 (2H, m), 7.88 (1H, d, J=2.4 Hz), 7.58-7.65 (2H, m), 7.19 (2H, dd, J=8.8 Hz, J=8.8 Hz)

Mass spectrometric value (ESI-MS) 395 (M−1)

Compound 361 Pyridin-2-carboxylic acid [4-chloro-2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-amide

The title compound 361 was produced in the same manner as in Example 1.

¹H-NMR (CD₃OD, 400 MHz): δ 8.78 (1H, d, J=9.0 Hz), 8.73 (1H, d, J=4.6 Hz), 8.31 (1H, s), 8.22 (1H, d, J=7.8 Hz), 7.98-8.04 (1H, m), 7.88 (1H, d, J=2.4 Hz), 7.72 (1H, s), 7.56-7.66 (3H, m), 7.24-7.35 (2H, m), 2.40 (3H, s)

Mass spectrometric value (ESI-MS) 391 (M−1)

Compound 362 Pyridin-2-carboxylic acid [4-chloro-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-amide

The title compound 362 was produced in the same manner as in Example 1.

¹H-NMR (CD₃OD, 400 MHz): δ 8.78 (1H, d, J=8.8 Hz), 8.73 (1H, d, J=4.9 Hz), 8.30 (1H, s), 8.22 (1H, d, J=7.8 Hz), 8.01 (1H, ddd, J=8.5 Hz, J=8.5 Hz, J=1.7 Hz), 7.87 (1H, d, J=2.4 Hz), 7.75 (2H, d, J=8.0 Hz), 7.57-7.64 (2H, m), 7.27 (2H, d, J=8.0 Hz), 2.38 (3H, s)

Mass spectrometric value (ESI-MS) 391 (M−1)

Compound 363 Pyridin-2-carboxylic acid [4-chloro-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-amide

The title compound 363 was produced in the same manner as in Example 1.

¹H-NMR (CD₃OD, 400 MHz): δ 8.77 (1H, d, J=9.0 Hz), 8.73 (1H, d, J=4.4 Hz), 8.27 (1H, s), 8.22 (1H, d, J=7.8 Hz), 8.00 (1H, ddd, J=1.7 Hz, J=7.7 Hz, J=7.7 Hz), 7.87 (1H, d, J=2.4 Hz), 7.67 (1H, s), 7.53-7.64 (3H, m), 7.20 (1H, d, J=7.8 Hz), 2.32 (3H, s), 2.30 (3H, s)

Mass spectrometric value (ESI-MS) 405 (M−1)

Compound 364 Pyridin-2-carboxylic acid [4-chloro-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-amide

The title compound 364 was produced in the same manner as in Example 1.

¹H-NMR (CD₃OD, 400 MHz): δ 8.79 (1H, d, J=9.0 Hz), 8.71-8.75 (1H, m), 8.35-8.40 (2H, m), 8.22 (1H, d, J=7.8 Hz), 8.07 (1H, d, J=8.3 Hz), 7.98-8.04 (1H, m), 7.90 (1H, d, J=2.2 Hz), 7.70 (1H, d, J=8.6 Hz), 7.58-7.67 (2H, m)

Mass spectrometric value (ESI-MS) 479 (M−1)

Compound 366 N-{4-Chloro-2-[N′-(3,4-dimethyl-benzyl)-hydrazinocarbonyl]-phenyl}-3-(pyridin-4-ylsulfanylmethyl)-benzamide

The title compound 366 was produced in the same manner as in Example 7.

Mass spectrometric value (ESI-MS) 529, 531, 532 (M−1)

Example 7

Compound 367 N-{4-Bromo-2-[N′-(4-methyl-benzyl)-hydrazinocarbonyl]-phenyl}-3,4-dimethoxy-benzamide

Compound 62: N-[4-bromo-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-3,4-dimethoxy-benzamide (100 mg) produced in the same manner as in Example 1 was dissolved in a mixed solution (2.0 ml) of tetrahydrofuran/methanol=4/1, and sodium borohydride (14.0 mg) was added to the mixed solution at room temperature. The mixture was stirred at that temparature for 30 min, and, after the completion of the reaction was comfirmed by TLC, distilled water (2.0 ml) was poured thereinto. The mixture was subjected to separatory extraction with chloroform, and the organic layer was dried over sodium sulfate and was then concentrated under the reduced pressure. The residue was purified by preparative TLC to give the title compound 367 (42.2 mg).

¹H-NMR (CD₃OD, 400 MHz): δ 8.66 (1H, d, J=8.8 Hz), 8.35 (1H, s), 8.06 (1H, s), 7.87-7.95 (4H, m), 7.63 (1H, d, J=8.8 Hz), 7.62 (1H, d, J=8.8 Hz), 7.50 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.19 (2H, dd, J=8.8 Hz), 3.83 (2H, s), 3.65 (4H, t, J=5.9 Hz), 2.71 (4H, t, J=5.9 Hz)

Mass spectrometric value (ESI-MS) 496, 497, 498, 499 (M−1)

Compound 368 3-[1,4′]Bipiperidinyl-1′-ylmethyl-N-[4-chloro-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 368 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.64 (1H, d, J=8.8 Hz), 8.35 (1H, s), 7.89-7.98 (3H, m), 7.70 (1H, d, J=9.8 Hz), 7.57-7.64 (3H, m), 7.42-7.50 (2H, m), 7.10-7.23 (1H, m), 3.62 (2H, s), 2.99 (2H, d, J=12.0 Hz), 2.59 (4H, bs), 2.29-2.39 (1H, m), 2.06 (2H, t, J=11.5 Hz), 1.86 (2H, d, J=11.7 Hz), 1.55-1.68 (6H, m), 1.40-1.50 (2H, m)

Mass spectrometric value (ESI-MS) 574, 576 (M−1)

Compound 369 3-[1,4′]Bipiperidinyl-1′-ylmethyl-N-[4-chloro-2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 369 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.63 (1H, d, J=9.0 Hz), 8.35 (1H, s), 7.88-7.97 (5H, m), 7.56-7.64 (2H, m), 7.52 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.15-7.22 (2H, m), 3.62 (2H, s), 3.98 (2H, d, J=12.2 Hz), 2.57 (4H, bs), 2.25-2.35 (1H, m), 2.05 (2H, t, J=11.1 Hz), 1.80-1.90 (2H, m), 1.53-1.66 (7H, m), 1.40-1.50 (2H, m)

Mass spectrometric value (ESI-MS) 574, 576 (M−1)

Compound 370 3-[1,4′]Bipiperidinyl-1′-ylmethyl-N-[4-chloro-2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 370 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.53 (1H, d, J=9.0 Hz), 8.33 (1H, s), 7.88-7.98 (4H, m), 7.71 (1H, s), 7.57-7.65 (3H, m), 7.52 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.25-7.37 (2H, m), 3.63 (2H, s), 3.99 (2H, d, J=12.0 Hz), 2.56 (4H, bs), 2.39 (3H, s), 2.25-2.37 (1H, m), 2.06 (2H, t, J=11.3 Hz), 1.80-1.90 (2H, m), 1.55-1.64 (6H, m), 1.40-1.49 (2H, m)

Mass spectrometric value (ESI-MS) 570, 571 (M−1)

Compound 371 3-[1,4′]Bipiperidinyl-1′-ylmethyl-N-[4-chloro-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 371 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.64 (1H, d, J=9.0 Hz), 8.33 (1H, s), 7.89-7.98 (3H, m), 7.74 (2H, d, J=8.3 Hz), 7.57-7.64 (2H, m), 7.52 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.27 (2H, d, J=7.8 Hz), 3.63 (2H, s), 2.95-3.05 (2H, m), 2.56 (4H, bs), 2.39 (3H, s), 2.25-2.35 (1H, m), 2.00-2.10 (2H, m), 1.80-1.90 (2H, m), 1.59 (6H, bs), 1.40-1.50 (2H, m)

Mass spectrometric value (ESI-MS) 570, 571 (M−1)

Compound 372 3-[1,4′]Bipiperidinyl-1′-ylmethyl-N-[4-chloro-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 372 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.64 (1H, d, J=9.0 Hz), 8.30 (1H, s), 7.96 (1H, s), 7.89-7.95 (2H, m), 7.65 (1H, s), 7.49-7.68 (4H, m), 7.20 (1H, d, J=8.0 Hz), 3.62 (2H, s), 2.99 (2H, d, J=11.5 Hz), 2.55 (4H, bs), 2.32 (3H, s), 2.30 (3H, s), 2.25-2.30 (1H, m), 2.01-2.10 (2H, m), 1.80-1.88 (2H, m), 1.54-1.65 (6H, m), 1.40-1.50 (2H, m)

Mass spectrometric value (ESI-MS) 584, 585 (M−1)

Compound 373 3-[1,4′]Bipiperidinyl-1′-ylmethyl-N-[4-chloro-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 373 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.63 (1H, d, J=9.0 Hz), 8.35 (1H, s), 8.05 (1H, d, J=8.3 Hz), 7.89-7.98 (4H, m), 7.71 (1H, d, J=8.6 Hz), 7.64 (1H, dd, J=9.0 Hz, J=2.2 Hz), 7.56-7.62 (1H, m), 7.53 (1H, dd, J=7.6 Hz, J=7.6 Hz), 3.66 (2H, s), 3.00-3.10 (6H, m), 2.09-2.18 (3H, m), 1.96-2.03 (2H, m), 1.70-1.80 (6H, m), 1.55-1.65 (2H, m)

Mass spectrometric value (ESI-MS) 658, 660 (M−1)

Compound 374 3-[1,4′]Bipiperidinyl-1′-ylmethyl-N-[4-chloro-2-(3-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 374 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.62 (1H, d, J=9.0 Hz), 8.32 (1H, s), 7.87-7.98 (4H, m), 7.47-7.65 (4H, m), 7.28-7.38 (2H, m), 6.97-7.03 (1H, m), 3.86 (3H, s), 3.61 (3H, s), 2.97 (2H, d, J=10.5 Hz), 2.55 (4H, bs), 2.25-2.35 (1H, m), 1.97-2.10 (2H, m), 1.80-1.88 (2H, m), 1.54-1.65 (6H, m), 1.44 (2H, bs)

Mass spectrometric value (ESI-MS) 586, 588 (M−1)

Compound 375 3-[1,4′]Bipiperidinyl-1′-ylmethyl-N-[4-chloro-2-(4-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 375 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.64 (1H, d, J=9.0 Hz), 8.30 (1H, s), 7.96 (1H, s), 7.89-7.94 (2H, m), 7.79 (2H, d, J=8.8 Hz), 7.57-7.64 (2H, m), 7.52 (1H, dd, J=7.6 Hz, J=7.6 Hz), 6.99 (2H, d, J=8.8 Hz), 3.85 (3H, s), 3.62 (2H, s), 3.99 (2H, d, J=12.0 Hz), 2.56 (4H, bs), 2.25-2.35 (1H, m), 2.05 (2H, t, J=11.0 Hz), 1.80-1.90 (2H, m), 1.55-1.65 (6H, m), 1.40-1.50 (2H, m)

Mass spectrometric value (ESI-MS) 586, 587 (M−1)

Compound 376 3-[1,4′]Bipiperidinyl-1′-ylmethyl-N-[4-chloro-2-(3-hydroxy-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 376 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.64 (1H, d, J=9.0 Hz), 8.29 (1H, s), 7.89-7.98 (4H, m), 7.62 (1H, dd, J=2.4 Hz, J=9.0 Hz), 7.59 (1H, d, J=7.8 Hz), 7.52 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.32 (1H, s), 7.20-7.30 (2H, m), 6.85-6.90 (1H, m), 3.64 (2H, s), 3.02 (2H, d, J=11.7 Hz), 2.66 (4H, bs), 2.32 (1H, bs), 2.08 (2H, t, J=11.4 Hz), 1.85-1.93 (2H, m), 1.52-1.68 (6H, m), 1.40-1.51 (2H, m)

Mass spectrometric value (ESI-MS) 572, 574 (M−1)

Compound 377 3-[1,4′]Bipiperidinyl-1′-ylmethyl-N-[4-chloro-2-(4-hydroxy-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 377 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.64 (1H, d, J=9.0 Hz), 8.26 (1H, s), 7.96 (1H, s), 7.88-7.94 (2H, m), 7.70 (1H, d, J=8.8 Hz), 7.62 (2H, d, J=2.4 Hz), 7.57-7.63 (2H, m), 7.52 (1H, dd, J=7.6 Hz, J=7.6 Hz), 6.84 (2H, d, J=8.5 Hz), 3.63 (2H, s), 2.99 (2H, d, J=12.0 Hz), 2.57 (4H, bs), 2.27-2.36 (1H, m), 2.06 (2H, t, J=11.2 Hz), 1.85 (2H, d, J=12.7 Hz), 1.52-1.67 (6H, m), 1.40-1.50 (2H, m)

Mass spectrometric value (ESI-MS) 572, 574, 575 (M−1)

Compound 378 4-[1,4′]Bipiperidinyl-1′-ylmethyl-N-{4-bromo-2-[N′-(3-methoxy-benzyl)-hydrazinocarbonyl]-phenyl}-benzamide

The title compound 378 was produced in the same manner as in Example 7.

Mass spectrometric value (ESI-MS) 632, 634 (M−1)

Compound 379 N-[4-Chloro-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-3-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 379 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.64 (1H, d, J=9.0 Hz), 8.35 (1H, s), 7.90-8.00 (2H, m), 7.89 (1H, s), 7.70 (1H, d, J=9.8 Hz), 7.56-7.63 (3H, m), 7.53 (1H, dd, J=7.7 Hz), 7.43-7.49 (1H, m), 3.67 (2H, s), 2.69-2.75 (2H, m), 2.54-2.64 (6H, m), 2.28 (3H, s), 1.03 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 536, 538 (M−1)

Compound 380 N-[4-Chloro-2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-3-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 380 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.64 (1H, d, J=9.0 Hz), 8.35 (1H, s), 7.98 (1H, s), 7.94 (1H, d, J=2.2 Hz), 7.87-7.93 (3H, m), 7.58-7.64 (2H, m), 7.53 (1H, dd, J=7.4 Hz, J=7.4 Hz), 7.19 (2H, dd, J=8.8 Hz, J=8.8 Hz), 3.67 (2H, s), 2.68-2.74 (2H, m), 2.53-2.63 (6H, m), 2.28 (3H, s), 1.02 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 536, 538 (M−1)

Compound 381 N-[4-Chloro-2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 381 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.65 (1H, d, J=9.0 Hz), 8.33 (1H, s), 7.99 (1H, s), 7.89-7.96 (2H, m), 7.71 (2H, s), 7.58-7.65 (2H, m), 7.53 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.25-7.35 (2H, m), 3.67 (2H, s), 2.67-2.75 (2H, m), 2.51-2.62 (6H, m), 2.39 (3H, s), 2.28 (3H, s), 1.01 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 532, 534 (M−1)

Compound 382 N-[4-Chloro-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 382 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.64 (1H, d, J=9.0 Hz), 8.33 (1H, s), 7.98 (1H, s), 7.88-7.94 (2H, m), 7.73 (2H, d, J=8.3 Hz), 7.58-7.63 (2H, m), 7.52 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.26 (2H, d, J=8.0 Hz), 3.67 (2H, s), 2.68-2.74 (2H, m), 2.53-2.63 (6H, m), 2.38 (3H, s), 2.28 (3H, s), 1.02 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 532, 534 (M−1)

Compound 383 N-[4-Chloro-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 383 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.65 (1H, d, J=9.0 Hz), 8.30 (1H, s), 7.99 (1H, s), 7.89-7.95 (2H, m), 7.66 (1H, s), 7.58-7.64 (2H, m), 7.50-7.57 (2H, m), 7.20 (1H, d, J=8.1 Hz), 3.67 (2H, s), 2.68-2.75 (2H, m), 2.54-2.63 (6H, m), 2.32 (3H, s), 2.31 (3H, s), 2.29 (3H, s), 1.02 (6H, t, J=7.3 Hz)

Mass spectrometric value (ESI-MS) 546, 548 (M−1)

Compound 384 N-[4-Chloro-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 384 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.63 (1H, d, J=8.8 Hz), 8.38 (1H, s), 8.33 (1H, s), 8.03 (1H, d, J=8.3 Hz), 7.95-8.00 (2H, m), 7.92 (1H, d, J=7.8 Hz), 7.68 (1H, d, J=8.3 Hz), 7.57-7.64 (2H, m), 7.53 (1H, s), 3.66 (2H, s), 2.71-2.79 (2H, m), 2.54-2.66 (6H, m), 2.28 (3H, s), 1.03 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 620, 622 (M−1)

Compound 385 N-[4-Chloro-2-(3-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-3-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 385 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.64 (1H, d, J=9.0 Hz), 8.33 (1H, s), 7.98 (1H, s), 7.89-7.96 (2H, m), 7.49-7.63 (4H, m), 7.27-7.37 (2H, m), 6.95-7.05 (1H, m), 3.86 (3H, s), 3.66 (2H, s), 2.67-2.73 (2H, m), 2.53-2.62 (6H, m), 2.27 (3H, s), 1.02 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 548, 550 (M−1)

Compound 386 N-[4-Chloro-2-(4-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-3-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 386 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.64 (1H, d, J=9.0 Hz), 8.30 (1H, s), 7.98 (1H, s), 7.88-7.95 (2H, m), 7.79 (2H, d, J=9.0 Hz), 7.58-7.64 (2H, m), 7.52 (1H, dd, J=7.7 Hz, J=7.7 Hz), 6.99 (2H, d, J=8.8 Hz), 3.84 (3H, s), 3.66 (2H, s), 2.67-2.73 (2H, m), 2.52-2.62 (6H, m), 2.28 (3H, s), 1.02 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 548, 550 (M−1)

Compound 387 N-[4-Chloro-2-(3-hydroxy-benzylidene-hydrazinocarbonyl)-phenyl]-3-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 387 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.64 (1H, d, J=9.0 Hz), 8.29 (1H, s), 7.91 (1H, s), 7.88-7.95 (2H, m), 7.61 (2H, dd, J=2.2 Hz, J=9.0 Hz), 7.53 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.21-7.34 (3H, m), 6.85-6.90 (1H, ddd, J=2.2 Hz, J=2.2 Hz, J=6.8 Hz), 3.67 (2H, s), 2.70-2.75 (2H, m), 2.54-2.64 (6H, m), 2.28 (3H, s), 1.02 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 534, 536 (M−1)

Compound 388 N-[4-Chloro-2-(4-hydroxy-benzylidene-hydrazinocarbonyl)-phenyl]-3-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 388 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.65 (1H, d, J=9.0 Hz), 8.27 (1H, s), 7.98 (1H, s), 7.88-7.95 (2H, m), 7.70 (2H, d, J=8.8 Hz), 7.61 (2H, dd, J=1.8 Hz, J=8.8 Hz), 7.53 (1H, dd, J=7.7 Hz, J=7.7 Hz), 6.84 (2H, d, J=8.8 Hz), 3.68 (2H, s), 2.76 (2H, t, J=7.3 Hz), 2.55-2.68 (6H, m), 2.29 (3H, s), 1.04 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 534, 536 (M−1)

Compound 389 N-[4-Chloro-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-3-(1H-[1,2,4]triazol-3-ylsulfanylmethyl)-benzamide

The title compound 389 was produced in the same manner as in Example 4.

Mass spectrometric value (ESI-MS) 506 (M−1)

Compound 390 N-[4-Chloro-2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-3-(1H-[1,2,4]triazol-3-ylsulfanylmethyl)-benzamide

The title compound 390 was produced in the same manner as in Example 4.

Mass spectrometric value (ESI-MS) 506 (M−1)

Compound 391 N-[4-Chloro-2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-(1H-[1,2,4]triazol-3-ylsulfanylmethyl)-benzamide

The title compound 391 was produced in the same manner as in Example 4.

Mass spectrometric value (ESI-MS) 503, 504 (M−1)

Compound 392 N-[4-Chloro-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-(1H-[1,2,4]triazol-3-ylsulfanylmethyl)-benzamide

The title compound 392 was produced in the same manner as in Example 4.

Mass spectrometric value (ESI-MS) 503, 504 (M−1)

Compound 393 N-[4-Chloro-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-(1H-[1,2,4]triazol-3-ylsulfanylmethyl)-benzamide

The title compound 393 was produced in the same manner as in Example 4.

Mass spectrometric value (ESI-MS) 591, 593 (M−1)

Compound 394 N-[4-Chloro-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-3-{[(2-hydroxy-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 394 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.64 (1H, d, J=9.0 Hz), 8.35 (1H, s), 8.00 (1H, s), 7.88-7.95 (2H, m), 7.71 (1H, d, J=9.3 Hz), 7.58-7.67 (3H, m), 7.53 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.42-7.50 (1H, m), 7.15-7.22 (1H, m), 3.69-3.74 (4H, m), 2.62 (2H, t, J=6.0 Hz), 2.30 (3H, s)

Mass spectrometric value (ESI-MS) 481, 483 (M−1)

Compound 395 N-[4-Chloro-2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-3-{[(2-hydroxy-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 395 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.63 (1H, d, J=9.0 Hz), 8.35 (1H, s), 7.95-8.02 (2H, m), 7.87-7.95 (3H, m), 7.63 (1H, d, J=9.0 Hz), 7.62 (1H, d, J=9.0 Hz), 7.52 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.19 (2H, dd, J=8.8 Hz, J=8.8 Hz), 3.69-3.75 (4H, m), 2.62 (2H, t, J=6.0 Hz), 2.30 (3H, s)

Mass spectrometric value (ESI-MS) 481, 483 (M−1)

Compound 396 N-[4-Chloro-2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-{[(2-hydroxy-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 396 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.65 (1H, d, J=8.8 Hz), 8.33 (1H, s), 7.99 (1H, s), 7.88-7.95 (3H, m), 7.71 (1H, s), 7.60-7.65 (3H, m), 7.52 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.25-7.36 (2H, m), 3.68-3.74 (4H, m), 2.61 (2H, t, J=6.0 Hz), 2.39 (3H, s), 2.29 (3H, s)

Mass spectrometric value (ESI-MS) 477 (M−1)

Compound 397 N-[4-Chloro-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-{[(2-hydroxy-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 397 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.64 (1H, d, J=9.0 Hz), 8.33 (1H, s), 8.00 (1H, bs), 7.90-7.95 (2H, m), 7.74 (2H, d, J=7.8 Hz), 7.60-7.65 (2H, m), 7.53 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.27 (2H, d, J=7.8 Hz), 3.70-3.78 (4H, m), 2.65 (2H, t, J=6.0 Hz), 2.38 (3H, s), 2.32 (3H, s)

Mass spectrometric value (ESI-MS) 477 (M−1)

Compound 398 N-[4-Chloro-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-{[(2-hydroxy-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 398 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.65 (1H, d, J=9.0 Hz), 8.30 (1H, s), 8.00 (1H, bs), 7.90-7.95 (2H, m), 7.66 (1H, s), 7.59-7.65 (2H, m), 7.50-7.57 (2H, m), 7.20 (1H, d, J=7.8 Hz), 3.76 (2H, s), 3.73 (2H, t, J=6.0 Hz), 2.66 (2H, t, J=6.0 Hz), 2.33 (3H, s), 2.31 (3H, s), 2.30 (3H, s)

Mass spectrometric value (ESI-MS) 491 (M−1)

Compound 399 N-[4-Chloro-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-{[(2-hydroxy-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 399 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.63 (1H, d, J=9.0 Hz), 8.39 (1H, s), 8.34 (1H, s), 8.03-8.08 (1H, m), 8.00 (1H, s), 7.94 (1H, d, J=2.4 Hz), 7.90 (1H, d, J=8.3 Hz), 7.70 (1H, d, J=8.5 Hz), 7.58-7.67 (2H, m), 7.52 (1H, dd, J=7.6 Hz, J=7.6 Hz), 3.68-3.74 (4H, m), 2.60 (2H, t, J=6.0 Hz), 2.28 (3H, s)

Mass spectrometric value (ESI-MS) 565 (M−1)

Compound 400 N-[4-Chloro-2-(3-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-3-{[(2-hydroxy-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 400 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.64 (1H, d, J=9.0 Hz), 8.33 (1H, s), 7.99 (1H, s), 7.88-7.94 (2H, m), 7.58-7.64 (2H, m), 7.57 (1H, s), 7.48-7.54 (1H, m), 7.26-7.36 (2H, m), 6.97-7.02 (1H, m), 3.86 (3H, s), 3.68-3.74 (4H, m), 2.61 (2H, t, J=6.1 Hz), 2.29 (3H, s)

Mass spectrometric value (ESI-MS) 493, 495 (M−1)

Compound 401 N-[4-Chloro-2-(4-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-3-{[(2-hydroxy-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 401 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.65 (1H, d, J=9.0 Hz), 8.31 (1H, s), 7.99 (1H, s), 7.75-7.93 (5H, m), 7.58-7.65 (2H, m), 7.53 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.00 (1H, d, J=8.8 Hz), 3.85 (3H, s), 3.67-3.74 (4H, m), 2.63 (2H, t, J=6.1 Hz), 2.31 (3H, s)

Mass spectrometric value (ESI-MS) 493, 494 (M−1)

Compound 402 N-[4-Chloro-2-(3-hydroxy-benzylidene-hydrazinocarbonyl)-phenyl]-3-{[(2-hydroxy-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 402 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.63 (1H, d, J=9.0 Hz), 8.29 (1H, s), 7.99 (1H, s), 7.88-7.94 (3H, m), 7.62 (2H, d, J=7.8 Hz), 7.52 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.31 (1H, bs), 7.23-7.28 (2H, m), 3.68-3.74 (4H, m), 2.61 (2H, t, J=6.1 Hz), 2.29 (3H, s)

Mass spectrometric value (ESI-MS) 479 (M−1)

Compound 403 N-[4-Chloro-2-(4-hydroxy-benzylidene-hydrazinocarbonyl)-phenyl]-3-{[(2-hydroxy-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 403 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.65 (1H, d, J=9.0 Hz), 8.27 (1H, s), 7.99 (1H, s), 7.89-7.94 (3H, m), 7.71 (2H, d, J=8.7 Hz), 7.58-7.65 (2H, m), 7.52 (1H, dd, J=7.7 Hz, J=7.7 Hz), 6.84 (2H, d, J=8.7 Hz), 3.71 (2H, t, J=6.1 Hz), 3.70 (2H, s), 2.61 (2H, t, J=6.1 Hz), 2.29 (3H, s)

Mass spectrometric value (ESI-MS) 479, 481 (M−1)

Compound 404 3-{[Bis-(2-hydroxy-ethyl)-amino]-methyl}-N-[4-chloro-2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 404 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.67 (1H, d, J=9.0 Hz), 8.34 (1H, s), 8.07 (1H, s), 7.94 (1H, d, J=2.4 Hz), 7.90 (1H, d, J=7.8 Hz), 7.74 (1H, s), 7.61-7.66 (3H, m), 7.51 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.25-7.37 (2H, m), 3.83 (2H, s), 3.66 (4H, t, J=5.9 Hz), 2.71 (4H, t, J=5.9 Hz), 2.40 (3H, s)

Mass spectrometric value (ESI-MS) 507, 509 (M−1)

Compound 405 3-{[Bis-(2-hydroxy-ethyl)-amino]-methyl}-N-[4-chloro-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 405 was produced in the same manner as in Example 5.

Mass spectrometric value (ESI-MS) 507, 508 (M−1)

Compound 406 3-{[Bis-(2-hydroxy-ethyl)-amino]-methyl}-N-[4-chloro-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 406 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.67 (1H, d, J=9.0 Hz), 8.30 (1H, s), 8.06 (1H, s), 7.92 (1H, d, J=2.4 Hz), 7.87-7.91 (1H, m), 7.68 (1H, s), 7.60-7.65 (2H, m), 7.47-7.58 (2H, m), 7.20 (1H, d, J=7.8 Hz), 3.83 (2H, s), 3.65 (4H, t, J=5.8 Hz), 2.71 (4H, t, J=5.8 Hz), 2.32 (3H, s), 2.30 (3H, s)

Mass spectrometric value (ESI-MS) 521, 522 (M−1)

Compound 407 3-{[Bis-(2-hydroxy-ethyl)-amino]-methyl}-N-[4-chloro-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 407 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.66 (1H, d, J=8.8 Hz), 8.39 (1H, s), 8.37 (1H, s), 8.05-8.10 (2H, m), 7.95 (1H, d, J=2.2 Hz), 7.84-7.92 (1H, m), 7.70 (1H, d, J=8.3 Hz), 7.60-7.68 (2H, m), 7.48-7.53 (1H, dd, J=7.8 Hz, J=7.8 Hz), 3.83 (2H, s), 3.65 (4H, t, J=5.8 Hz), 2.71 (4H, t, J=5.8 Hz)

Mass spectrometric value (ESI-MS) 595, 597 (M−1)

Compound 408 3-{[Bis-(2-hydroxy-ethyl)-amino]-methyl}-N-[4-chloro-2-(3-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 408 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.66 (1H, d, J=9.0 Hz), 8.33 (1H, s), 8.06 (1H, s), 7.89-7.96 (2H, m), 7.58-7.66 (3H, m), 7.48-7.54 (1H, m), 7.28-7.38 (2H, m), 6.97-7.04 (1H, m), 3.87 (3H, s), 3.85 (2H, s), 3.66 (4H, t, J=5.9 Hz), 2.72 (4H, t, J=5.9 Hz)

Mass spectrometric value (ESI-MS) 523, 525 (M−1)

Compound 409 3-{[Bis-(2-hydroxy-ethyl)-amino]-methyl}-N-[4-chloro-2-(4-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 409 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.66 (1H, d, J=9.0 Hz), 8.31 (1H, s), 8.06 (1H, s), 7.80-7.94 (4H, m), 7.60-7.66 (2H, m), 7.50 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.00 (1H, d, J=9.0 Hz), 3.90 (3H, s), 3.85 (2H, s), 3.66 (4H, t, J=5.9 Hz), 2.71 (4H, t, J=5.9 Hz)

Mass spectrometric value (ESI-MS) 523, 525 (M−1)

Compound 410 3-{[Bis-(2-hydroxy-ethyl)-amino]-methyl}-N-[4-chloro-2-(3-hydroxy-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 410 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.65 (1H, d, J=9.0 Hz), 8.29 (1H, s), 8.05 (1H, s), 7.93 (1H, d, J=2.4 Hz), 7.87-7.92 (1H, m), 7.60-7.66 (2H, m), 7.50 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.33 (1H, s), 7.26 (2H, d, J=4.9 Hz), 6.85-6.92 (1H, m), 3.83 (2H, s), 3.66 (4H, t, J=5.9 Hz), 2.71 (4H, t, J=5.9 Hz)

Mass spectrometric value (ESI-MS) 509 (M−1)

Compound 411 3-{[Bis-(2-hydroxy-ethyl)-amino]-methyl}-N-[4-chloro-2-(4-hydroxy-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 411 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.67 (1H, d, J=9.0 Hz), 8.27 (1H, s), 8.06 (1H, s), 7.85-7.93 (2H, m), 7.72 (2H, d, J=8.8 Hz), 7.60-7.65 (2H, m), 7.47-7.54 (1H, m), 6.85 (2H, d, J=8.6 Hz), 3.83 (2H, s), 3.65 (4H, t, J=5.9 Hz), 2.71 (4H, t, J=5.9 Hz)

Mass spectrometric value (ESI-MS) 509, 511 (M−1)

Compound 412 N-[4-Chloro-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-4-{[(2-hydroxy-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 412 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.65 (1H, d, J=9.0 Hz), 8.36 (1H, s), 7.98 (2H, d, J=8.3 Hz), 7.94 (1H, d, J=2.4 Hz), 7.68-7.74 (1H, m), 7.58-7.65 (2H, m), 7.55 (2H, d, J=8.3 Hz), 7.43-7.50 (1H, m), 7.10-7.23 (1H, m), 3.69 (2H, t, J=6.1 Hz), 3.67 (2H, s), 2.58 (2H, t, J=6.1 Hz), 2.28 (3H, s)

Mass spectrometric value (ESI-MS) 482 (M−1)

Compound 413 N-[4-Chloro-2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-4-{[(2-hydroxy-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 413 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.65 (1H, d, J=9.0 Hz), 8.36 (1H, s), 7.98 (2H, d, J=8.3 Hz), 7.87-7.95 (3H, m), 7.63 (1H, dd, J=2.4 Hz, J=9.0 Hz), 7.55 (2H, d, J=7.8 Hz), 7.19 (2H, dd, J=8.7 Hz, J=8.7 Hz), 3.69 (2H, t, J=6.0 Hz), 3.67 (2H, s), 2.58 (2H, t, J=6.0 Hz), 2.28 (3H, s)

Mass spectrometric value (ESI-MS) 481, 483 (M−1)

Compound 414 N-[4-Chloro-2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-{[(2-hydroxy-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 414 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.66 (1H, d, J=9.0 Hz), 8.34 (1H, s), 7.98 (2H, d, J=8.0 Hz), 7.93 (1H, d, J=2.4 Hz), 7.72 (1H, s), 7.60-7.65 (2H, m), 7.55 (2H, d, J=8.0 Hz), 7.26-7.36 (2H, m), 3.69 (2H, t, J=6.1 Hz), 3.67 (2H, s), 2.58 (2H, t, J=6.1 Hz), 2.40 (3H, s), 2.28 (3H, s)

Mass spectrometric value (ESI-MS) 477, 479 (M−1)

Compound 415 N-[4-Chloro-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-{[(2-hydroxy-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 415 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.66 (1H, d, J=9.0 Hz), 8.33 (1H, s), 7.98 (2H, d, J=8.0 Hz), 7.93 (1H, d, J=2.5 Hz), 7.74 (2H, d, J=8.0 Hz), 7.62 (1H, dd, J=2.5 Hz, J=9.0 Hz), 7.55 (2H, d, J=8.0 Hz), 7.27 (2H, d, J=7.8 Hz), 3.69 (2H, t, J=6.1 Hz), 3.67 (3H, s), 2.58 (2H, t, J=6.1 Hz), 2.39 (3H, s), 2.27 (3H, s)

Mass spectrometric value (ESI-MS) 477 (M−1)

Compound 416 N-[4-Chloro-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-{[(2-hydroxy-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 416 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.66 (1H, d, J=9.0 Hz), 8.30 (1H, s), 7.98 (2H, d, J=8.3 Hz), 7.92 (1H, d, J=2.4 Hz), 7.66 (1H, s), 7.61 (1H, dd, J=2.4 Hz, J=9.0 Hz), 7.52-7.57 (3H, m), 7.20 (1H, d, J=8.0 Hz), 3.69 (2H, d, J=8.0 Hz), 3.67 (2H, s), 2.58 (2H, t, J=6.1 Hz), 2.32 (3H, s), 2.30 (3H, s), 2.27 (3H, s)

Mass spectrometric value (ESI-MS) 491, 493 (M−1)

Compound 417 N-[4-Chloro-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-{[(2-hydroxy-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 417 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.55 (1H, d, J=9.0 Hz), 8.30 (1H, s), 8.25 (1H, s), 7.93-7.98 (1H, m), 7.83-7.90 (3H, m), 7.60 (1H, d, J=8.3 Hz), 7.54 (1H, dd, J=2.3 Hz, J=8.8 Hz), 7.46 (2H, d, J=8.3 Hz), 3.59 (2H, t, J=6.0 Hz), 3.58 (2H, s), 2.49 (2H, t, J=6.0 Hz), 2.18 (3H, s)

Mass spectrometric value (ESI-MS) 565, 567 (M−1)

Compound 418 N-[4-Chloro-2-(3-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-4-{[(2-hydroxy-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 418 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.56 (1H, d, J=9.0 Hz), 8.24 (1H, s), 7.82-7.90 (3H, m), 7.42-7.55 (4H, m), 7.18-7.27 (2H, m), 6.88-6.94 (1H, m), 3.77 (3H, s), 3.56-3.61 (4H, m), 2.50 (2H, t, J=6.0 Hz), 2.18 (3H, s)

Mass spectrometric value (ESI-MS) 493, 495 (M−1)

Compound 419 N-[4-Chloro-2-(4-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-4-{[(2-hydroxy-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 419 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.56 (1H, d, J=9.0 Hz), 8.21 (1H, s), 7.88 (2H, d, J=8.3 Hz), 7.81 (1H, d, J=2.2 Hz), 7.69 (2H, d, J=8.8 Hz), 7.50 (1H, dd, J=2.4 Hz, J=8.8 Hz), 7.45 (2H, d, J=8.3 Hz), 6.89 (2H, d, J=8.8 Hz), 3.75 (3H, s), 3.59 (2H, t, J=6.1 Hz), 3.59 (2H, s), 2.50 (2H, t, J=6.1 Hz), 2.19 (3H, s)

Mass spectrometric value (ESI-MS) 493, 495 (M−1)

Compound 420 N-[4-Chloro-2-(3-hydroxy-benzylidene-hydrazinocarbonyl)-phenyl]-4-{[(2-hydroxy-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 420 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.55 (1H, d, J=8.8 Hz), 8.19 (1H, s), 7.88 (2H, d, J=7.8 Hz), 7.82-7.85 (1H, m), 7.50-7.55 (1H, m), 7.46 (2H, d, J=7.6 Hz), 7.22 (1H, s), 7.13-7.18 (2H, m), 6.75-6.82 (1H, m), 3.56-3.62 (4H, m), 2.49 (2H, t, J=6.1 Hz), 2.19 (3H, s)

Mass spectrometric value (ESI-MS) 479, 481 (M−1)

Compound 421 N-[4-Chloro-2-(4-hydroxy-benzylidene-hydrazinocarbonyl)-phenyl]-4-{[(2-hydroxy-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 421 was produced in the same manner as in Example 5.

Mass spectrometric value (ESI-MS) 479, 481 (M−1)

Compound 422 N-[4-Chloro-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-3-{[ethyl-(2-hydroxy-ethyl)-amino]-methyl}-benzamide

The title compound 422 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.55 (1H, d, J=9.0 Hz), 8.26 (1H, s), 7.93 (1H, s), 7.84 (1H, d, J=2.4 Hz), 7.78-7.83 (1H, m), 7.33-7.70 (6H, m), 7.05-7.20 (1H, m), 3.72 (2H, s), 3.57 (2H, t, J=6.1 Hz), 2.59 (2H, t, J=6.0 Hz), 2.54 (3H, q, J=7.3 Hz), 1.02 (3H, t, J=7.1 Hz)

Mass spectrometric value (ESI-MS) 495 (M−1)

Compound 423 N-[4-Chloro-2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-3-{[ethyl-(2-hydroxy-ethyl)-amino]-methyl}-benzamide

The title compound 423 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.54 (1H, d, J=9.0 Hz), 8.26 (1H, s), 7.92 (1H, s), 7.77-7.85 (4H, m), 7.53 (2H, dd, J=2.2 Hz, J=9.0 Hz), 7.41 (1H, dd, J=7.7. Hz, J=7.7. Hz), 7.09 (2H, dd, J=8.8 Hz, J=8.8 Hz), 3.68 (2H, s), 3.57 (2H, t, J=6.2 Hz), 2.57 (2H, t, J=6.3 Hz), 2.53 (2H, q, J=7.1 Hz), 1.01 (3H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 495 (M−1)

Compound 424 N-[4-Chloro-2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-{[ethyl-(2-hydroxy-ethyl)-amino]-methyl}-benzamide

The title compound 424 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.56 (1H, d, J=9.0 Hz), 8.24 (1H, s), 7.92 (1H, s), 7.83 (1H, d, J=2.4 Hz), 7.78-7.82 (1H, m), 7.62 (1H, s), 7.53 (2H, dd, J=2.2 Hz, J=9.0 Hz), 7.42 (2H, dd, J=7.4 Hz, J=7.4 Hz), 7.15-7.26 (2H, m), 3.69 (2H, s), 3.57 (2H, t, J=6.3 Hz), 2.57 (2H, t, J=6.3 Hz), 2.53 (2H, q, J=7.2 Hz), 2.30 (3H, s), 1.01 (3H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 491 (M−1), 515 (M+23)

Compound 425 N-[4-Chloro-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-{[ethyl-(2-hydroxy-ethyl)-amino]-methyl}-benzamide

The title compound 425 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.65 (1H, d, J=9.0 Hz), 8.33 (1H, s), 8.01 (1H, s), 7.88-7.94 (2H, m), 7.74 (2H, d, J=8.1 Hz), 7.60-7.65 (2H, m), 7.51 (2H, m), 7.26 (2H, d, J=8.1 Hz), 3.80 (2H, s), 3.67 (2H, t, J=6.2 Hz), 2.69 (2H, t, J=6.2 Hz), 2.64 (2H, q, J=7.1 Hz), 2.38 (3H, s), 1.11 (3H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 491 (M−1), 515 (M+23)

Compound 426 N-[4-Chloro-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-{[ethyl-(2-hydroxy-ethyl)-amino]-methyl}-benzamide

The title compound 426 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.66 (1H, d, J=9.0 Hz), 8.30 (1H, s), 8.02 (1H, s), 7.89-7.94 (2H, m), 7.60-7.69 (3H, m), 7.49-7.57 (2H, m), 7.21 (1H, d, J=7.8 Hz), 3.82 (2H, s), 3.68 (2H, t, J=6.2 Hz), 2.70 (2H, t, J=6.2 Hz), 2.66 (2H, q, J=7.1 Hz), 2.32 (3H, s), 2.30 (3H, s), 1.12 (3H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 505 (M−1)

Compound 427 N-[4-Chloro-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-{[ethyl-(2-hydroxy-ethyl)-amino]-methyl}-benzamide

The title compound 427 was produced in the same manner as in Example 5.

Mass spectrometric value (ESI-MS) 579 (M−1)

Compound 428 N-[4-Chloro-2-(3-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-3-{[ethyl-(2-hydroxy-ethyl)-amino]-methyl}-benzamide

The title compound 428 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.65 (1H, d, J=8.8 Hz), 8.33 (1H, s), 8.01 (1H, s), 7.93 (1H, d, J=2.2. Hz), 7.89 (1H, d, J=2.2. Hz), 7.56-7.66 (3H, m), 7.50 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.29-7.37 (2H, m), 6.97-7.04 (1H, m), 3.86 (3H, s), 3.77 (2H, s), 3.66 (2H, t, J=6.2 Hz), 2.66 (2H, t, J=6.4 Hz), 2.61 (2H, q, J=7.4 Hz), 1.10 (3H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 507 (M−1)

Compound 429 N-[4-Chloro-2-(4-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-3-{[ethyl-(2-hydroxy-ethyl)-amino]-methyl}-benzamide

The title compound 429 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.65 (1H, d, J=9.0 Hz), 8.30 (1H, s), 8.01 (1H, s), 7.91 (1H, d, J=2.4 Hz), 7.87-7.91 (1H, m), 7.80 (2H, d, J=8.8 Hz), 7.59-7.65 (2H, m), 7.51 (1H, dd, J=7.7 Hz, J=7.7 Hz), 6.99 (2H, d, J=8.8 Hz), 3.85 (3H, s), 3.78 (2H, s), 3.66 (2H, t, J=6.2 Hz), 2.67 (2H, t, J=6.3 Hz), 2.62 (2H, q, J=7.2 Hz), 1.10 (3H, t, J=7.1 Hz)

Mass spectrometric value (ESI-MS) 507 (M−1)

Compound 430 N-[4-Chloro-2-(3-hydroxy-benzylidene-hydrazinocarbonyl)-phenyl]-3-{[ethyl-(2-hydroxy-ethyl)-amino]-methyl}-benzamide

The title compound 430 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.65 (1H, d, J=8.8 Hz), 8.29 (1H, s), 8.01 (1H, s), 7.93 (1H, d, J=2.2 Hz), 7.89 (1H, d, J=7.6 Hz), 7.60-7.66 (2H, m), 7.51 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.22-7.40 (3H, m), 3.78 (2H, s), 3.66 (2H, t, J=6.4 Hz), 2.67 (2H, t, J=6.4 Hz), 2.62 (2H, q, J=7.3 Hz), 1.10 (3H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 493 (M−1)

Compound 431 N-[4-Chloro-2-(4-hydroxy-benzylidene-hydrazinocarbonyl)-phenyl]-3-{[ethyl-(2-hydroxy-ethyl)-amino]-methyl}-benzamide

The title compound 431 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.65 (1H, d, J=8.8 Hz), 8.27 (1H, s), 8.00 (1H, s), 7.86-7.94 (2H, m), 7.70 (2H, d, J=8.8 Hz), 7.58-7.65 (2H, m), 7.50 (1H, dd, J=7.7 Hz, J=7.7 Hz), 6.84 (2H, d, J=8.6 Hz), 3.77 (2H, s), 3.66 (2H, t, J=6.3 Hz), 2.66 (2H, t, J=6.3 Hz), 2.62 (2H, q, J=7.2 Hz), 1.10 (3H, t, J=7.1 Hz)

Mass spectrometric value (ESI-MS) 493 (M−1)

Compound 432 N-[4-Chloro-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-4-{[ethyl-(2-hydroxy-ethyl)-amino]-methyl}-benzamide

The title compound 432 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.65 (1H, d, J=9.0 Hz), 8.36 (1H, s), 7.92-8.00 (3H, m), 7.71 (1H, d, J=9.5 Hz), 7.54-7.65 (4H, m), 7.43-7.51 (1H, m), 7.15-7.23 (1H, m), 3.75 (2H, s), 3.63 (2H, t, J=6.2 Hz), 2.64 (2H, t, J=6.2 Hz), 2.60 (2H, q, J=7.3 Hz), 1.09 (3H, t, J=7.1 Hz)

Mass spectrometric value (ESI-MS) 495 (M−1)

Compound 433 N-[4-Chloro-2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-4-{[ethyl-(2-hydroxy-ethyl)-amino]-methyl}-benzamide

The title compound 433 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.65 (1H, d, J=8.8 Hz), 8.35 (1H, s), 7.96 (2H, d, J=8.3 Hz), 7.87-7.94 (3H, m), 7.61 (1H, dd, J=2.4 Hz, J=9.0 Hz), 7.55 (2H, d, J=8.0 Hz), 7.19 (2H, dd, J=8.8 Hz, J=8.8 Hz), 3.74 (2H, s), 3.63 (2H, t, J=6.2 Hz), 2.64 (2H, t, J=6.3 Hz), 2.60 (2H, q, J=7.2 Hz), 1.09 (3H, t, J=7.1 Hz)

Mass spectrometric value (ESI-MS) 495 (M−1)

Compound 434 N-[4-Chloro-2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-{[ethyl-(2-hydroxy-ethyl)-amino]-methyl}-benzamide

The title compound 434 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.66 (1H, d, J=8.8 Hz), 8.33 (1H, s), 7.97 (2H, d, J=8.3 Hz), 7.93 (1H, d, J=2.4 Hz), 7.12 (1H, s), 7.60-7.65 (2H, m), 7.56 (2H, d, J=8.3 Hz), 7.25-7.36 (2H, m), 3.74 (2H, s), 3.63 (2H, t, J=6.2 Hz), 2.64 (2H, t, J=6.3 Hz), 2.60 (2H, q, J=7.1 Hz), 2.40 (3H, s), 1.09 (3H, t, J=7.1 Hz)

Mass spectrometric value (ESI-MS) 491 (M−1)

Compound 435 N-[4-Chloro-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-{[ethyl-(2-hydroxy-ethyl)-amino]-methyl}-benzamide

The title compound 435 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.66 (1H, d, J=9.0 Hz), 8.33 (1H, s), 7.97 (2H, d, J=8.3 Hz), 7.92 (1H, d, J=2.2 Hz), 7.89 (1H, s), 7.74 (2H, d, J=8.0 Hz), 7.61 (1H, dd, J=2.4 Hz, J=8.8 Hz), 7.27 (1H, d, J=8.0 Hz), 3.77 (2H, s), 3.64 (2H, t, J=6.2 Hz), 2.67 (2H, t, J=6.3 Hz), 2.63 (2H, q, J=7.1 Hz), 2.38 (3H, s), 1.10 (3H, t, 7.2 Hz)

Mass spectrometric value (ESI-MS) 491 (M−1)

Compound 436 N-[4-Chloro-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-{[ethyl-(2-hydroxy-ethyl)-amino]-methyl}-benzamide

The title compound 436 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.66 (1H, d, J=8.8 Hz), 8.30 (1H, s), 7.97 (2H, d, J=8.3 Hz), 7.92 (1H, d, J=2.4 Hz), 7.52-7.68 (5H, m), 7.20 (1H, d, J=7.8 Hz), 3.77 (2H, s), 3.64 (2H, t, J=6.2 Hz), 2.67 (2H, t, J=6.2 Hz), 2.63 (2H, q, J=7.2 Hz), 2.32 (3H, s), 2.31 (3H, s), 1.10 (3H, t, J=7.1 Hz)

Mass spectrometric value (ESI-MS) 505 (M−1)

Compound 437 N-[4-Chloro-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-{[ethyl-(2-hydroxy-ethyl)-amino]-methyl}-benzamide

The title compound 437 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.64 (1H, d, J=9.0 Hz), 8.39 (1H, s), 8.34 (1H, s), 8.05 (1H, d, J=8.1 Hz), 7.93-7.98 (2H, m), 7.89 (1H, s), 7.70 (1H, d, J=8.3 Hz), 7.63 (1H, dd, J=2.4 Hz, J=9.0 Hz), 7.56 (2H, d, J=8.3 Hz), 3.75 (2H, s), 3.63 (2H, t, J=6.4 Hz), 2.64 (2H, t, J=6.4 Hz), 2.60 (2H, q, J=7.1 Hz), 1.09 (3H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 579 (M−1)

Compound 438 N-[4-Chloro-2-(3-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-4-{[ethyl-(2-hydroxy-ethyl)-amino]-methyl}-benzamide

The title compound 438 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.66 (1H, d, J=8.8 Hz), 8.33 (1H, s), 7.92-7.99 (3H, m), 7.62 (1H, dd, J=2.2 Hz, J=8.8 Hz), 7.54-7.60 (3H, m), 7.28-7.37 (2H, m), 6.98-7.04 (1H, m), 3.87 (3H, s), 3.74 (2H, s), 3.63 (2H, t, J=6.2 Hz), 2.64 (2H, t, J=6.3 Hz), 2.60 (2H, q, J=7.2 Hz), 1.09 (3H, t, J=7.1 Hz)

Mass spectrometric value (ESI-MS) 507 (M−1)

Compound 439 N-[4-Chloro-2-(4-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-4-{[ethyl-(2-hydroxy-ethyl)-amino]-methyl}-benzamide

The title compound 439 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.66 (1H, d, J=9.0 Hz), 8.31 (1H, s), 7.96 (2H, d, J=8.3 Hz), 7.92 (1H, d, J=2.4 Hz), 7.80 (2H, d, J=8.8 Hz), 7.61 (1H, dd, J=2.4 Hz, J=9.0 Hz), 7.56 (2H, d, J=8.3 Hz), 6.99 (2H, d, J=8.8 Hz), 3.85 (3H, s), 3.74 (2H, s), 3.63 (2H, t, J=6.4 Hz), 2.65 (2H, t, J=6.4 Hz), 2.60 (2H, q, J=7.2 Hz), 1.09 (3H, t, J=7.1 Hz)

Mass spectrometric value (ESI-MS) 507 (M−1)

Compound 440 N-[4-Chloro-2-(3-hydroxy-benzylidene-hydrazinocarbonyl)-phenyl]-4-{[ethyl-(2-hydroxy-ethyl)-amino]-methyl}-benzamide

The title compound 440 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.65 (1H, d, J=8.8 Hz), 8.29 (1H, s), 7.88-7.99 (3H, m), 7.62 (1H, dd, J=2.4 Hz, J=9.0 Hz), 7.56 (2H, d, J=8.3 Hz), 7.30-7.33 (1H, m), 7.23-7.27 (2H, m), 6.85-6.91 (1H, m), 3.75 (2H, s), 3.63 (2H, t, J=6.3 Hz), 2.65 (2H, t, J=6.2 Hz), 2.61 (2H, q, J=7.1 Hz), 1.09 (3H, t, J=7.1 Hz)

Mass spectrometric value (ESI-MS) 493 (M−1)

Compound 441 N-[4-Chloro-2-(4-hydroxy-benzylidene-hydrazinocarbonyl)-phenyl]-4-{[ethyl-(2-hydroxy-ethyl)-amino]-methyl}-benzamide

The title compound 441 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.66 (1H, d, J=8.8 Hz), 8.27 (1H, s), 7.97 (2H, d, J=8.1 Hz), 7.91 (1H, d, J=2.4 Hz), 7.70 (2H, d, J=8.8 Hz), 7.61 (1H, dd, J=2.4 Hz, J=9.0 Hz), 7.56 (2H, d, J=8.3 Hz), 6.85 (2H, d, J=8.8 Hz), 3.78 (2H, s), 3.64 (2H, t, J=6.2 Hz), 2.68 (2H, t, J=6.2 Hz), 2.64 (2H, q, J=7.2 Hz), 1.10 (3H, t, J=7.1 Hz)

Mass spectrometric value (ESI-MS) 493 (M−1)

Compound 442 N-[4-Chloro-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-4-(2-diethylamino-ethylsulfanylmethyl)-benzamide

The title compound 442 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.65 (1H, d, J=9.0 Hz), 8.36 (1H, s), 7.97 (2H, d, J=8.3 Hz), 7.94 (1H, d, J=2.4 Hz), 7.71 (1H, d, J=8.1 Hz), 7.58-7.65 (2H, m), 7.55 (2H, d, J=8.3 Hz), 7.43-7.50 (1H, m), 7.15-7.25 (1H, m), 3.85 (2H, s), 2.60-2.67 (2H, m), 2.50-2.59 (6H, m), 1.00 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 539 (M−1)

Compound 443 N-[4-Chloro-2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-4-(2-diethylamino-ethylsulfanylmethyl)-benzamide

The title compound 443 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.65 (1H, d, J=9.0 Hz), 8.35 (1H, s), 7.97 (2H, d, J=8.3 Hz), 7.88-7.95 (3H, m), 7.62 (1H, dd, J=2.2 Hz, J=8.8 Hz), 7.55 (1H, d, J=8.3 Hz), 7.19 (2H, dd, J=8.7 Hz, J=8.7 Hz), 3.85 (1H, s), 2.49-2.67 (8H, m), 1.00 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 539 (M−1)

Compound 444 N-[4-Chloro-2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-(2-diethylamino-ethylsulfanylmethyl)-benzamide

The title compound 444 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.66 (1H, d, J=8.8 Hz), 8.33 (1H, s), 7.97 (2H, d, J=8.3 Hz), 7.93 (1H, d, J=2.4 Hz), 7.72 (1H, s), 7.60-7.65 (2H, m), 7.55 (2H, d, J=8.3 Hz), 7.25-7.36 (2H, m), 3.84 (2H, s), 2.48-2.66 (8H, m), 2.39 (3H, s), 1.00 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 535 (M−1)

Compound 445 N-[4-Chloro-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-(2-diethylamino-ethylsulfanylmethyl)-benzamide

The title compound 445 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.66 (1H, d, J=8.8 Hz), 8.33 (1H, s), 7.97 (2H, d, J=8.3 Hz), 7.93 (1H, d, J=2.4 Hz), 7.74 (2H, d, J=7.8 Hz), 7.61 (1H, dd, J=2.2 Hz, J=9.0 Hz), 7.55 (2H, d, J=8.3 Hz), 7.27 (2H, d, J=7.8 Hz), 3.84 (2H, s), 2.47-2.66 (8H, m), 2.39 (3H, s), 1.00 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 535 (M−1)

Compound 446 N-[4-Chloro-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-(2-diethylamino-ethylsulfanylmethyl)-benzamide

The title compound 446 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.66 (1H, d, J=9.0 Hz), 8.33 (1H, s), 7.96 (2H, d, J=8.3 Hz), 7.91 (1H, d, J=2.4 Hz), 7.65 (1H, s), 7.60 (1H, dd, J=2.4 Hz, J=9.0 Hz), 7.51-7.56 (3H, m), 7.19 (1H, d, J=7.8 Hz), 3.83 (2H, s), 2.58-2.65 (2H, m), 2.48-2.58 (6H, m), 2.31 (3H, s), 2.29 (3H, s), 0.99 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 549 (M−1)

Compound 447 N-[4-Chloro-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-(2-diethylamino-ethylsulfanylmethyl)-benzamide

The title compound 447 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.64 (1H, d, J=9.0 Hz), 8.39 (1H, s), 8.35 (1H, s), 8.05 (1H, d, J=8.3 Hz), 7.93-7.99 (3H, m), 7.70 (1H, d, J=8.3 Hz), 7.63 (1H, dd, J=2.4 Hz, J=9.0 Hz), 7.55 (2H, d, J=8.0 Hz), 3.85 (2H, s), 2.50-2.68 (8H, m), 1.00 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 623 (M−1)

Compound 448 N-[4-Chloro-2-(3-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-4-(2-diethylamino-ethylsulfanylmethyl)-benzamide

The title compound 448 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.66 (1H, d, J=9.0 Hz), 8.33 (1H, s), 7.92-8.00 (3H, m), 7.63 (1H, dd, J=2.4 Hz, J=9.0 Hz), 7.59 (1H, s), 7.55 (2H, d, J=8.0 Hz), 7.28-7.38 (2H, m), 6.98-7.03 (1H, m), 3.88 (3H, s), 3.84 (2H, s), 2.58-2.66 (2H, m), 2.47-2.58 (6H, m), 0.99 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 551 (M−1)

Compound 449 N-[4-Chloro-2-(4-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-4-(2-diethylamino-ethylsulfanylmethyl)-benzamide

The title compound 449 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.66 (1H, d, J=9.0 Hz), 8.31 (1H, s), 7.97 (2H, d, J=8.3 Hz), 7.92 (1H, d, J=2.4 Hz), 7.80 (2H, d, J=8.8 Hz), 7.61 (1H, dd, J=2.4 Hz, J=9.0 Hz), 7.55 (2H, d, J=8.6 Hz), 7.00 (2H, d, J=8.8 Hz), 3.85 (3H, s), 3.84 (2H, s), 2.49-2.67 (8H, m), 1.00 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 551 (M−1)

Compound 450 N-[4-Chloro-2-(3-hydroxy-benzylidene-hydrazinocarbonyl)-phenyl]-4-(2-diethylamino-ethylsulfanylmethyl)-benzamide

The title compound 450 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.64 (1H, d, J=9.0 Hz), 8.29 (1H, s), 7.97 (2H, d, J=8.3 Hz), 7.93 (1H, d, J=2.4 Hz), 7.62 (1H, dd, J=2.4 Hz, J=8.8 Hz), 7.55 (2H, d, J=8.3 Hz), 7.31 (1H, s), 7.22-7.28 (2H, m), 6.83-6.91 (1H, m), 3.85 (2H, s), 2.57-2.66 (2H, m), 2.48-2.57 (6H, m), 1.00 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 537 (M−1)

Compound 451 N-[4-Chloro-2-(4-hydroxy-benzylidene-hydrazinocarbonyl)-phenyl]-4-(2-diethylamino-ethylsulfanylmethyl)-benzamide

The title compound 451 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.66 (1H, d, J=8.8 Hz), 8.27 (1H, s), 7.96 (2H, d, J=8.3 Hz), 7.91 (1H, d, J=2.4 Hz), 7.71 (2H, d, J=8.6 Hz), 7.61 (1H, dd, J=2.4 Hz, J=9.0 Hz), 7.55 (2H, d, J=8.3 Hz), 6.84 (2H, d, J=8.8 Hz), 3.84 (2H, s), 2.49-2.66 (8H, m), 1.00 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 537 (M−1)

Compound 452 N-[4-Chloro-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-3-(2-diethylamino-ethylsulfanylmethyl)-benzamide

The title compound 452 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.65 (1H, d, J=9.0 Hz), 8.36 (1H, s), 7.93-7.99 (2H, m), 7.89 (1H, d, J=8.3 Hz), 7.70 (1H, d, J=8.5 Hz), 7.52-7.65 (3H, m), 7.41-7.56 (2H, m), 7.15-7.23 (1H, m), 3.88 (2H, s), 2.42-2.66 (8H, m), 0.96 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 539 (M−1)

Compound 453 N-[4-Chloro-2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-3-(2-diethylamino-ethylsulfanylmethyl)-benzamide

The title compound 453 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.65 (1H, d, J=8.8 Hz), 8.36 (1H, s), 7.85-7.99 (5H, m), 7.57-7.65 (2H, m), 7.47-7.55 (1H, m), 7.12-7.23 (2H, m), 3.88 (2H, s), 2.46-2.65 (8H, m), 0.96 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 539 (M−1)

Compound 454 N-[4-Chloro-2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-(2-diethylamino-ethylsulfanylmethyl)-benzamide

The title compound 454 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.66 (1H, d, J=9.0 Hz), 8.34 (1H, s), 7.98 (1H, s), 7.89 (1H, d, J=7.1 Hz), 7.71 (1H, s), 7.59-7.66 (3H, m), 7.52 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.24-7.35 (2H, m), 3.88 (2H, s), 2.46-2.65 (8H, m), 2.39 (3H, s), 0.96 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 535 (M−1)

Compound 455 N-[4-Chloro-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-(2-diethylamino-ethylsulfanylmethyl)-benzamide

The title compound 455 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.65 (1H, d, J=9.0 Hz), 8.33 (1H, s), 7.97 (1H, s), 7.84-7.95 (2H, m), 7.73 (2H, d, J=8.1 Hz), 7.58-7.65 (2H, m), 7.51 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.26 (2H, d, J=7.8 Hz), 3.88 (2H, s), 2.46-2.66 (8H, m), 2.38 (3H, s), 0.96 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 535 (M−1)

Compound 456 N-[4-Chloro-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-(2-diethylamino-ethylsulfanylmethyl)-benzamide

The title compound 456 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.65 (1H, d, J=9.0 Hz), 8.30 (1H, s), 7.97 (1H, s), 7.87-7.94 (2H, m), 7.58-7.67 (3H, m), 7.48-7.56 (2H, m), 7.19 (1H, d, J=7.6 Hz), 3.88 (2H, s), 2.46-2.67 (8H, m), 2.31 (3H, s), 2.29 (3H, s), 0.96 (6H, q, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 549 (M−1)

Compound 457 N-[4-Chloro-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-(2-diethylamino-ethylsulfanylmethyl)-benzamide

The title compound 457 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.63 (1H, d, J=9.0 Hz), 8.40 (1H, s), 8.33 (1H, s), 8.04 (1H, d, J=7.8 Hz), 7.93-8.00 (2H, m), 7.89 (1H, d, J=7.1 Hz), 7.69 (1H, d, J=8.0 Hz), 7.60-7.65 (2H, m), 7.52 (1H, dd, J=7.6 Hz, J=7.6 Hz), 3.88 (2H, s), 2.58-2.67 (2H, m), 2.47-2.58 (6H, m), 0.97 (6H, t, J=7.1 Hz)

Mass spectrometric value (ESI-MS) 623 (M−1)

Compound 458 N-[4-Chloro-2-(3-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-3-(2-diethylamino-ethylsulfanylmethyl)-benzamide

The title compound 458 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.64 (1H, d, J=9.0 Hz), 8.34 (1H, s), 7.97 (1H, s), 7.93 (1H, d, J=2.4 Hz), 7.87-7.91 (1H, m), 7.59-7.65 (2H, m), 7.57 (1H, s), 7.51 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.28-7.37 (2H, m), 6.97-7.03 (1H, m), 3.87 (2H, s), 3.86 (3H, s), 2.46-2.65 (8H, m), 0.96 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 551 (M−1)

Compound 459 N-[4-Chloro-2-(4-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-3-(2-diethylamino-ethylsulfanylmethyl)-benzamide

The title compound 459 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.65 (1H, d, J=9.0 Hz), 8.31 (1H, s), 7.97 (1H, s), 7.92 (1H, d, J=2.4 Hz), 7.89 (1H, d, J=9.0 Hz), 7.79 (2H, d, J=8.8 Hz), 7.59-7.65 (2H, m), 7.51 (1H, dd, J=7.7 Hz, J=7.7 Hz), 6.99 (2H, d, J=8.8 Hz), 3.88 (2H, s), 3.84 (3H, s), 2.46-2.66 (8H, m), 0.96 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 551 (M−1)

Compound 460 N-[4-Chloro-2-(3-hydroxy-benzylidene-hydrazinocarbonyl)-phenyl]-3-(2-diethylamino-ethylsulfanylmethyl)-benzamide

The title compound 460 was produced in the same manner as in Example 5.

Mass spectrometric value (ESI-MS) 537 (M−1)

Compound 461 N-[4-Chloro-2-(4-hydroxy-benzylidene-hydrazinocarbonyl)-phenyl]-3-(2-diethylamino-ethylsulfanylmethyl)-benzamide

The title compound 461 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.66 (1H, d, J=9.0 Hz), 8.27 (1H, s), 7.97 (1H, s), 7.91 (1H, d, J=2.4 Hz), 7.89 (1H, d, J=7.6 Hz), 7.70 (2H, d, J=8.5 Hz), 7.58-7.65 (2H, m), 7.52 (1H, dd, J=7.8 Hz, J=7.8 Hz), 6.84 (2H, d, J=8.6 Hz), 3.88 (2H, s), 2.46-2.65 (8H, m), 0.96 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 537 (M−1)

Compound 462 N-[4-Chloro-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-3-[1-(2-dimethylamino-ethyl)-1H-tetrazol-5-ylsulfanylmethyl]-benzamide

The title compound 462 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.62 (1H, d, J=9.0 Hz), 8.36 (1H, s), 8.03 (1H, s), 7.93 (1H, d, J=2.2 Hz), 7.88-7.93 (2H, m), 7.69 (1H, d, J=10.0 Hz), 7.58-7.65 (3H, m), 7.42-7.52 (2H, m), 7.19 (1H, ddd, J=2.0 Hz, J=8.4 Hz, J=8.4 Hz), 4.63 (2H, s), 4.33 (2H, t, J=6.3 Hz), 2.67 (2H, t, J=6.3 Hz), 2.18 (6H, s)

Mass spectrometric value (ESI-MS) 579, 581 (M−1)

Compound 463 N-[4-Chloro-2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-3-[1-(2-dimethylamino-ethyl)-1H-tetrazol-5-ylsulfanylmethyl]-benzamide

The title compound 463 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.62 (1H, d, J=8.8 Hz), 8.36 (1H, s), 8.04 (1H, s), 7.87-7.94 (4H, m), 7.59-7.65 (2H, m), 7.48 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.19 (2H, dd, J=8.7 Hz, J=8.7 Hz), 4.63 (2H, s), 4.32 (2H, t, J=6.3 Hz), 2.67 (2H, t, J=6.3 Hz), 2.18 (6H, s)

Mass spectrometric value (ESI-MS) 579 (M−1)

Compound 464 N-[4-Chloro-2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-[1-(2-dimethylamino-ethyl)-1H-tetrazol-5-ylsulfanylmethyl]-benzamide

The title compound 464 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.63 (1H, d, J=9.0 Hz), 8.34 (1H, s), 8.04 (1H, s), 7.88-7.94 (2H, m), 7.70 (1H, s), 7.59-7.64 (3H, m), 7.49 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.25-7.36 (2H, m), 4.63 (2H, s), 4.32 (2H, s), 2.66 (2H, t, J=6.4 Hz), 2.39 (3H, s), 2.17 (6H, s)

Mass spectrometric value (ESI-MS) 575 (M−1)

Compound 465 N-[4-Chloro-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-[1-(2-dimethylamino-ethyl)-1H-tetrazol-5-ylsulfanylmethyl]-benzamide

The title compound 465 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.63 (1H, d, J=8.8 Hz), 8.33 (1H, s), 8.04 (1H, s), 7.88-7.94 (2H, m), 7.73 (2H, d, J=8.1 Hz), 7.61 (2H, dd, J=2.2 Hz, J=9.0 Hz), 7.48 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.27 (2H, d, J=8.1 Hz), 4.63 (2H, s), 4.32 (2H, t, J=6.3 Hz), 2.67 (2H, t, J=6.3 Hz), 2.38 (3H, s), 2.17 (6H, s)

Mass spectrometric value (ESI-MS) 575 (M−1)

Compound 466 N-[4-Chloro-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-[1-(2-dimethylamino-ethyl)-1H-tetrazol-5-ylsulfanylmethyl]-benzamide

The title compound 466 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.63 (1H, d, J=8.8 Hz), 8.30 (1H, s), 8.04 (1H, s), 7.89-7.95 (2H, m), 7.59-7.68 (3H, m), 7.54 (1H, d, J=8.0 Hz), 7.49 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.21 (1H, d), 4.63 (2H, s), 4.32 (2H, t, J=6.3 Hz), 2.66 (2H, t, J=6.3 Hz), 2.32 (3H, s), 2.31 (3H, s), 2.17 (6H, s)

Mass spectrometric value (ESI-MS) 589, 591 (M−1)

Compound 467 N-[4-Chloro-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-[1-(2-dimethylamino-ethyl)-1H-tetrazol-5-ylsulfanylmethyl]-benzamide

The title compound 467 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.60 (1H, d, J=9.0 Hz), 8.39 (1H, s), 8.31 (1H, s), 8.02-8.07 (2H, m), 7.93 (1H, d, J=2.2 Hz), 7.89 (1H, d, J=7.8 Hz), 7.69 (1H, d, J=8.3 Hz), 7.62 (2H, dd, J=2.2 Hz, J=8.8 Hz), 7.49 (1H, dd, J=7.7 Hz, J=7.7 Hz), 4.63 (2H, s), 4.32 (2H, t, J=6.4 Hz), 3.44 (1H, s), 2.67 (2H, t, J=6.3 Hz), 2.18 (6H, s)

Mass spectrometric value (ESI-MS) 663 (M−1)

Compound 468 N-[4-Chloro-2-(3-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-3-[1-(2-dimethylamino-ethyl)-1H-tetrazol-5-ylsulfanylmethyl]-benzamide

The title compound 468 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.63 (1H, d, J=9.0 Hz), 8.34 (1H, s), 8.04 (1H, s), 7.94 (1H, d, J=2.4 Hz), 7.91 (1H, d, J=8.3 Hz), 7.60-7.66 (2H, m), 7.57 (1H, s), 7.49 (1H, dd, J=7.8 Hz, J=7.8 Hz), 7.28-7.38 (2H, m), 6.98-7.04 (1H, m), 4.63 (2H, s), 4.32 (2H, t, J=6.4 Hz), 3.86 (3H, s), 3.44 (1H, s), 2.67 (2H, t, J=6.3 Hz), 2.17 (6H, s)

Mass spectrometric value (ESI-MS) 591 (M−1)

Compound 469 N-[4-Chloro-2-(4-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-3-[1-(2-dimethylamino-ethyl)-1H-tetrazol-5-ylsulfanylmethyl]-benzamide

The title compound 469 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.63 (1H, d, J=9.0 Hz), 8.31 (1H, s), 8.04 (1H, s), 7.88-7.94 (2H, m), 7.79 (2H, d, J=8.8 Hz), 7.58-7.64 (2H, m), 7.48 (1H, dd, J=7.7 Hz, J=7.7 Hz), 6.99 (2H, d, J=8.8 Hz), 4.63 (2H, s), 4.32 (2H, t, J=6.3 Hz), 3.84 (3H, s), 3.45 (1H, s), 2.67 (2H, t, J=6.3 Hz), 2.18 (6H, s)

Mass spectrometric value (ESI-MS) 591 (M−1)

Compound 470 N-[4-Chloro-2-(3-hydroxy-benzylidene-hydrazinocarbonyl)-phenyl]-3-[1-(2-dimethylamino-ethyl)-1H-tetrazol-5-ylsulfanylmethyl]-benzamide

The title compound 470 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.62 (1H, d, J=8.8 Hz), 8.29 (1H, s), 8.04 (1H, s), 7.89-7.95 (2H, m), 7.55-7.65 (2H, m), 7.48 (1H, dd, J=7.8 Hz, J=7.8 Hz), 7.31 (1H, s), 7.22-7.29 (2H, m), 6.86-6.90 (1H, m), 4.63 (2H, s), 4.32 (2H, s), 2.67 (2H, t, J=6.3 Hz), 2.17 (6H, s)

Mass spectrometric value (ESI-MS) 577 (M−1)

Compound 471 N-[4-Chloro-2-(4-hydroxy-benzylidene-hydrazinocarbonyl)-phenyl]-3-[1-(2-dimethylamino-ethyl)-1H-tetrazol-5-ylsulfanylmethyl]-benzamide

The title compound 471 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.63 (1H, d, J=9.0 Hz), 8.27 (1H, s), 8.04 (1H, s), 7.87-7.93 (2H, m), 7.69 (2H, d, J=8.5 Hz), 7.57-7.63 (2H, m), 7.48 (1H, dd, J=7.7 Hz, J=7.7 Hz), 6.84 (2H, d, J=8.5 Hz), 4.63 (2H, s), 4.32 (2H, t, J=6.4 Hz), 2.67 (2H, t, J=6.4 Hz), 2.17 (6H, s)

Mass spectrometric value (ESI-MS) 577 (M−1)

Compound 472 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[2-(3-fluoro-benzylidene-hydrazinocarbonyl)-4-iodo-phenyl]-benzamide

The title compound 472 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.44 (1H, d, J=8.8 Hz), 8.36 (1H, s), 8.23 (1H, s), 7.97 (1H, s), 7.88-7.95 (2H, m), 7.68 (1H, d, J=9.5 Hz), 7.42-7.63 (5H, m), 7.18 (1H, dd, J=8.4 Hz, J=8.4 Hz), 3.67 (2H, s), 2.78 (2H, t, J=7.1 Hz), 2.65 (4H, q, J=7.2 Hz), 2.58 (2H, t, J=7.2 Hz), 2.28 (3H, s), 1.04 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 628 (M−1)

Compound 473 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[2-(4-fluoro-benzylidene-hydrazinocarbonyl)-4-iodo-phenyl]-benzamide

The title compound 473 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.44 (1H, d, J=8.8 Hz), 8.36 (1H, s), 8.21 (1H, d, J=1.9 Hz), 7.86-7.99 (5H, m), 7.60 (1H, d, J=7.6 Hz), 7.52 (1H, dd, J=8.8 Hz, J=8.8 Hz), 7.18 (2H, dd, J=8.8 Hz, J=8.8 Hz), 3.67 (2H, s), 2.77 (2H, t, J=7.1 Hz), 2.64 (4H, q, J=7.2 Hz), 2.58 (2H, t, J=7.2 Hz), 2.28 (3H, s), 1.04 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 628 (M−1)

Compound 474 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[4-iodo-2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 474 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.45 (1H, d, J=8.8 Hz), 8.33 (1H, s), 8.22 (1H, d, J=1.1 Hz), 7.97 (1H, s), 7.88-7.93 (2H, m), 7.69 (1H, s), 7.58-7.63 (2H, m), 7.52 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.32 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.25 (1H, d, J=7.3 Hz), 3.66 (2H, s), 2.67-2.73 (2H, m), 2.52-2.61 (6H, m), 2.38 (3H, s), 2.27 (3H, s), 1.01 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 624 (M−1)

Compound 475 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[4-iodo-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 475 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.44 (1H, d, J=8.8 Hz), 8.33 (1H, s), 8.21 (1H, d, J=2.0 Hz), 7.97 (1H, s), 7.89-7.94 (2H, m), 7.72 (2H, d, J=8.0 Hz), 7.60 (1H, d, J=7.6 Hz), 7.52 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.26 (2H, d, J=7.8 Hz), 3.67 (2H, s), 2.75 (2H, t, J=7.2 Hz), 2.62 (4H, q, J=7.2 Hz), 2.57 (2H, t, J=7.2 Hz), 2.37 (3H, s), 2.28 (3H, s), 1.03 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 624 (M−1)

Compound 476 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-4-iodo-phenyl]-benzamide

The title compound 476 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.44 (1H, d, J=8.8 Hz), 8.30 (1H, s), 8.20 (1H, d, J=2.0 Hz), 7.97 (1H, s), 7.90 (2H, dd, J=2.0 Hz, J=8.8 Hz), 7.58-7.66 (2H, m), 7.48-7.56 (2H, m), 7.19 (1H, d, J=7.8 Hz), 3.66 (2H, s), 2.68-2.75 (2H, m), 2.53-2.64 (6H, m), 2.30 (3H, s), 2.29 (3H, s), 2.27 (3H, s), 1.02 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 638 (M−1)

Compound 477 N-[2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-iodo-phenyl]-3-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 477 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.43 (1H, d, J=8.8 Hz), 8.38 (1H, s), 8.32 (1H, s), 8.25 (1H, s), 8.02 (1H, d, J=0.6 Hz), 7.97 (1H, s), 7.88-7.94 (2H, m), 7.67 (1H, d, J=8.5 Hz), 7.60 (1H, d, J=7.3 Hz), 7.52 (1H, dd, J=7.6 Hz, J=7.6 Hz), 3.66 (2H, s), 2.75 (2H, t, J=7.2 Hz), 2.62 (4H, q, J=7.2 Hz), 2.56 (2H, t, J=7.2 Hz), 2.27 (3H, s), 1.03 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 712 (M−1)

Compound 478 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[4-iodo-2-(3-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 478 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.44 (1H, d, J=8.8 Hz), 8.33 (1H, s), 8.22 (1H, d, J=2.0 Hz), 7.97 (1H, s), 7.88-7.94 (2H, m), 7.60 (1H, d, J=7.6 Hz), 7.56 (1H, bs), 7.52 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.22-7.36 (2H, m), 6.97-7.03 (1H, m), 3.86 (3H, s), 3.66 (2H, s), 2.71 (2H, t, J=7.2 Hz), 2.53-2.62 (6H, m), 2.27 (3H, s), 1.02 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 640 (M−1)

Compound 479 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[4-iodo-2-(4-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 479 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.45 (1H, d, J=8.8 Hz), 8.31 (1H, s), 8.20 (1H, d, J=2.2 Hz), 7.97 (1H, s), 7.88-7.94 (2H, m), 7.78 (2H, d, J=8.8 Hz), 7.60 (1H, d, J=7.6 Hz), 7.52 (1H, dd, J=7.7 Hz, J=7.7 Hz), 6.99 (2H, d, J=8.8 Hz), 3.84 (3H, s), 3.67 (2H, s), 2.73 (2H, t, J=7.2 Hz), 2.60 (4H, q, J=7.2 Hz), 2.54-2.60 (2H, m), 2.28 (3H, s), 1.03 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 640 (M−1)

Compound 480 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[2-(3-hydroxy-benzylidene-hydrazinocarbonyl)-4-iodo-phenyl]-benzamide

The title compound 480 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.44 (1H, d, J=8.8 Hz), 8.29 (1H, s), 8.21 (1H, d, J=2.0 Hz), 7.97 (1H, s), 7.88-7.94 (2H, m), 7.60 (1H, d, J=7.6 Hz), 7.52 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.30 (1H, s), 7.20-7.28 (2H, m), 6.87 (1H, ddd, J=2.2 Hz, J=2.2 Hz, J=7.1 Hz), 3.66 (2H, s), 2.72 (2H, t, J=7.2 Hz), 2.59 (4H, q, J=7.2 Hz), 2.56 (2H, t, J=6.8 Hz), 2.27 (3H, s), 1.02 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 626 (M−1)

Compound 481 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[2-(4-hydroxy-benzylidene-hydrazinocarbonyl)-4-iodo-phenyl]-benzamide

The title compound 481 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.45 (1H, d, J=8.8 Hz), 8.27 (1H, s), 8.19 (1H, d, J=2.0 Hz), 7.97 (1H, s), 7.88-7.95 (2H, m), 7.69 (1H, d, J=8.5 Hz), 7.52 (1H, dd, J=7.7 Hz, J=7.7 Hz), 6.83 (2H, d, J=8.5 Hz), 3.67 (2H, s), 2.75 (2H, t, J=7.2 Hz), 2.62 (4H, q, J=7.2 Hz), 2.75-2.64 (2H, m), 2.28 (3H, s), 1.03 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 626 (M−1)

Compound 482 3-[1,4′]Bipiperidinyl-1′-ylmethyl-N-[2-(3-fluoro-benzylidene-hydrazinocarbonyl)-4-iodo-phenyl]-benzamide

The title compound 482 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.44 (1H, d, J=8.8 Hz), 8.36 (1H, s), 8.22 (1H, d, J=2.0 Hz), 7.87-7.97 (4H, m), 7.42-7.72 (4H, m), 7.14-7.23 (1H, m), 3.61 (2H, s), 2.98 (2H, d, J=11.5 Hz), 2.60 (4H, bs), 2.30-2.40 (1H, m), 2.05 (2H, t, J=11.2 Hz), 1.82-1.91 (2H, m), 1.55-1.66 (6H, m), 1.40-1.50 (2H, m)

Mass spectrometric value (ESI-MS) 666 (M−1)

Compound 483 3-[1,4′]Bipiperidinyl-1′-ylmethyl-N-[2-(4-fluoro-benzylidene-hydrazinocarbonyl)-4-iodo-phenyl]-benzamide

The title compound 483 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.43 (1H, d, J=8.8 Hz), 8.35 (1H, s), 8.21 (1H, d, J=2.0 Hz), 7.85-7.97 (5H, m), 7.58 (1H, d, J=7.8 Hz), 7.51 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.18 (2H, dd, J=8.7 Hz, J=8.7 Hz), 3.61 (2H, s), 2.98 (2H, d, J=12.0 Hz), 2.59 (4H, bs), 2.25-2.38 (1H, m), 2.05 (2H, t, J=11.5 Hz), 1.85 (2H, d, J=12.7 Hz), 1.54-1.66 (6H, m), 1.40-1.50 (2H, m)

Mass spectrometric value (ESI-MS) 666 (M−1)

Compound 484 3-[1,4′]Bipiperidinyl-1′-ylmethyl-N-[4-iodo-2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 484 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.44 (1H, d, J=8.8 Hz), 8.34 (1H, s), 8.21 (1H, d, J=1.9 Hz), 7.88-7.97 (3H, m), 7.68 (1H, s), 7.55-7.64 (2H, m), 7.50 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.21-7.34 (2H, m), 3.60 (2H, s), 2.97 (2H, d, J=10.8 Hz), 2.54 (4H, bs), 2.38 (3H, s), 2.25-2.35 (1H, m), 2.25-2.35 (1H, m), 2.03 (2H, t, J=11.7 Hz), 1.83 (2H, d, J=12.4 Hz), 1.50-1.65 (6H, m), 1.38-1.48 (2H, m)

Mass spectrometric value (ESI-MS) 662 (M−1)

Compound 485 3-[1,4′]Bipiperidinyl-1′-ylmethyl-N-[4-iodo-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 485 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.44 (1H, d, J=8.8 Hz), 8.33 (1H, s), 8.21 (1H, d, J=2.0 Hz), 7.87-7.97 (3H, m), 7.72 (2H, d, J=8.1 Hz), 7.58 (1H, d, J=7.6 Hz), 7.51 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.26 (2H, d, J=8.1 Hz), 3.61 (2H, s), 2.98 (2H, d, J=11.0 Hz), 2.55 (4H, bs), 2.37 (3H, s), 2.23-2.35 (1H, m), 2.05 (2H, t, J=11.7 Hz), 1.84 (2H, d, J=12.0 Hz), 1.53-1.66 (6H, m), 1.40-1.50 (2H, m)

Mass spectrometric value (ESI-MS) 662 (M−1)

Compound 486 3-[1,4′]Bipiperidinyl-1′-ylmethyl-N-[2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-4-iodo-phenyl]-benzamide

The title compound 486 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.44 (1H, d, J=8.8 Hz), 8.30 (1H, s), 8.19 (1H, d, J=2.2 Hz), 7.87-7.96 (3H, m), 7.62 (1H, s), 7.57 (1H, d, J=7.6 Hz), 7.51 (2H, d, J=7.6 Hz), 7.15-7.22 (1H, m), 3.60 (2H, s), 2.92-3.02 (2H, m), 2.52 (4H, bs), 2.29 (3H, s), 2.27 (3H, s), 2.20-2.33 (1H, m), 1.98-2.09 (2H, m), 1.78-2.87 (2H, m), 1.50-1.65 (6H, m), 1.38-1.48 (2H, m)

Mass spectrometric value (ESI-MS) 676 (M−1)

Compound 487 3-[1,4′]Bipiperidinyl-1′-ylmethyl-N-[2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-iodo-phenyl]-benzamide

The title compound 487 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.38-8.45 (2H, m), 8.24 (1H, s), 8.24 (1H, s), 8.03 (1H, d, J=8.0 Hz), 7.87-7.97 (3H, m), 7.68 (1H, d, J=8.3 Hz), 7.58 (1H, d, J=6.8 Hz), 7.51 (1H, dd, J=7.7 Hz, J=7.7 Hz), 3.61 (2H, s), 2.98 (2H, d, J=10.5 Hz), 2.59 (4H, s), 2.28-2.38 (1H, m), 2.04 (2H, t, J=11.7 Hz), 1.80-1.90 (2H, m98, 1.55-1.65 (6H, m), 1.41-1.50 (2H, m)

Mass spectrometric value (ESI-MS) 750 (M−1)

Compound 488 3-[1,4′]Bipiperidinyl-1′-ylmethyl-N-[4-iodo-2-(3-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 488 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.44 (1H, d, J=8.8 Hz), 8.34 (1H, s), 8.21 (1H, d, J=2.0 Hz), 7.87-7.97 (3H, m), 7.48-7.60 (3H, m), 7.27-7.36 (2H, m), 6.96-7.03 (1H, m), 3.85 (3H, s), 3.60 (2H, s), 2.97 (2H, d, J=11.2 Hz), 2.55 (4H, bs), 2.23-2.33 (1H, m), 2.03 (2H, t, J=11.6 Hz), 1.83 (2H, d, J=11.2 Hz), 1.53-1.65 (6H, m), 1.40-1.50 (2H, m)

Mass spectrometric value (ESI-MS) 678 (M−1)

Compound 489 3-[1,4′]Bipiperidinyl-1′-ylmethyl-N-[4-iodo-2-(4-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 489 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.44 (1H, d, J=8.8 Hz), 8.32 (1H, s), 8.18-8.22 (1H, m), 7.87-7.97 (3H, m), 7.75-7.82 (2H, m), 7.55-7.62 (1H, m), 7.45-7.55 (1H, m), 6.95-7.03 (2H, m), 3.84 (3H, s), 3.61 (2H, s), 2.93-3.02 (2H, m), 2.56 (4H, bs), 2.20-2.35 (1H, m), 2.00-2.10 (2H, m), 1.80-1.88 (2H, m), 1.55-1.65 (6H, m), 1.40-1.50 (2H, m)

Mass spectrometric value (ESI-MS) 678 (M−1)

Compound 490 3-[1,4′]Bipiperidinyl-1′-ylmethyl-N-[2-(3-hydroxy-benzylidene-hydrazinocarbonyl)-4-iodo-phenyl]-benzamide

The title compound 490 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.43 (1H, d, J=8.8 Hz), 8.29 (1H, s), 8.19-8.22 (1H, m), 7.87-7.97 (3H, m), 7.57 (1H, d, J=7.3 Hz), 7.47-7.53 (1H, m), 7.30 (1H, s), 7.18-7.27 (2H, m), 6.83-6.89 (1H, m), 3.61 (2H, s), 2.98 (2H, d, J=10.5 Hz), 2.56 (4H, bs), 2.25-2.35 (1H, m), 2.04 (2H, t, J=12.0 Hz), 1.84 (2H, d, J=12.0 Hz), 1.53-1.66 (6H, m), 1.40-1.50 (2H, m)

Mass spectrometric value (ESI-MS) 664 (M−1)

Compound 491 3-[1,4′]Bipiperidinyl-1′-ylmethyl-N-[2-(4-hydroxy-benzylidene-hydrazinocarbonyl)-4-iodo-phenyl]-benzamide

The title compound 491 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.44 (1H, dd, J=3.7 Hz, J=8.8 Hz), 8.27 (1H, s), 8.18 (1H, bs), 7.86-7.96 (3H, m), 7.65-7.72 (2H, m), 7.54-7.61 (1H, m), 7.47-7.54 (1H, m), 6.79-6.86 (2H, m), 3.59-3.64 (2H, m), 2.93-3.03 (4H, m), 2.57 (4H, bs), 2.25-2.37 (1H, m), 1.95-2.10 (2H, m), 1.80-1.90 (2H, m), 1.58 (6H, bs), 1.45 (2H, bs)

Mass spectrometric value (ESI-MS) 664 (M−1)

Compound 492 N-{4-Chloro-2-[N′-(3,4-dimethyl-benzyl)-hydrazinocarbonyl]-phenyl}-3-(2-hydroxy-ethylsulfanylmethyl)-benzamide

The title compound 492 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.60 (1H, d, J=8.8 Hz), 7.90 (1H, s), 7.78 (1H, d, J=7.6 Hz), 7.59-7.70 (2H, m), 7.45-7.55 (2H, m), 7.09-7.13 (2H, m), 7.01 (1H, d, J=7.8 Hz), 3.96 (2H, s), 3.86 (2H, s), 3.67 (2H, t, J=6.8 Hz), 2.58 (2H, t, J=6.8 Hz), 2.16 (3H, s), 2.09 (3H, s)

Mass spectrometric value (ESI-MS) 496, 498, 499 (M−1)

Compound 493 N-[4-Chloro-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-(2-hydroxy-ethanesulfonylmethyl)-benzamide

The title compound 493 was produced in the same manner as in Example 6.

¹H-NMR (CD₃OD, 400 MHz): δ 8.67 (1H, d, J=9.0 Hz), 8.31 (1H, s), 8.11 (1H, s), 8.04 (1H, d, J=8.0 Hz), 7.94 (1H, d, J=2.4 Hz), 7.73 (1H, d, J=8.0 Hz), 7.67 (1H, s), 7.58-7.64 (2H, m), 7.54 (1H, d, J=7.3 Hz), 7.21 (1H, d, J=7.6 Hz), 4.63 (2H, s), 4.06 (2H, t, J=5.6 Hz), 3.20 (2H, t, J=5.7 Hz), 2.32 (3H, s), 2.32 (3H, s)

Mass spectrometric value (ESI-MS) 526, 528, 529 (M−1)

Compound 494 N-[4-Bromo-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-methyl-benzamide

The title compound 494 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 8.52 (1H, d, J=8.8 Hz), 8.33 (1H, s), 7.93 (2H, d, J=7.8 Hz), 7.65-7.74 (3H, m), 7.54 (1H, d, J=8.5 Hz), 7.21-7.30 (4H, m), 2.24 (3H, s), 2.38 (3H, s)

Mass spectrometric value (ESI-MS) 448, 450 (M−1)

Compound 495 Pyridin-2-carboxylic acid[4-bromo-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-amide

The title compound 495 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 8.72 (1H, s), 8.67 (1H, d, J=9.0 Hz), 8.28 (1H, s), 8.22 (1H, d, J=7.8 Hz), 7.86-7.92 (2H, m), 7.66 (1H, dd, J=2.2 Hz, J=8.8 Hz), 7.51-7.60 (2H, m), 7.46-7.51 (1H, m), 7.33-7.39 (1H, m), 7.03-7.10 (1H, m)

Mass spectrometric value (ESI-MS) 439, 441 (M−1)

Compound 496 Pyridin-2-carboxylic acid [4-bromo-2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-amide

The title compound 496 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 8.70 (1H, d, J=4.1 Hz), 8.65 (1H, d, J=9.0 Hz), 8.29 (1H, s), 8.21 (1H, d, J=7.8 Hz), 7.84-7.91 (2H, m), 7.74-7.81 (2H, m), 7.61-7.66 (1H, m), 7.44-7.50 (1H, m), 7.06 (2H, dd, J=8.5 Hz, J=8.5 Hz)

Mass spectrometric value (ESI-MS) 439, 441 (M−1)

Compound 497 Pyridin-2-carboxylic acid [4-bromo-2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-amide

The title compound 497 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 8.69 (1H, s), 8.65 (1H, d, J=9.0 Hz), 8.29 (1H, s), 8.22 (1H, d, J=7.8 Hz), 7.79-7.89 (2H, m), 7.57-7.66 (2H, m), 7.48-7.54 (1H, m), 7.41-7.46 (1H, m), 7.21-7.27 (1H, m), 7.11-7.17 (1H, m), 2.35 (3H, s)

Mass spectrometric value (ESI-MS) 435, 437 (M−1)

Compound 498 Pyridin-2-carboxylic acid [4-bromo-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-amide

The title compound 498 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 8.63 (1H, d, J=3.9 Hz), 8.58 (1H, d, J=9.0 Hz), 8.24 (1H, s), 8.16 (1H, d, J=8.1 Hz), 7.77-7.84 (2H, m), 7.52-7.62 (3H, m), 7.37-7.42 (1H, m), 7.11 (2H, d, J=8.1 Hz), 2.25 (3H, s)

Mass spectrometric value (ESI-MS) 435, 437 (M−1)

Compound 499 Pyridin-2-carboxylic acid [4-bromo-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-amide

The title compound 499 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 8.69 (1H, s), 8.65 (1H, d, J=9.0 Hz), 8.24 (1H, s), 8.21 (1H, d, J=7.8 Hz), 7.80-7.89 (2H, m), 7.57-7.63 (2H, m), 7.42-7.47 (2H, m), 7.12 (1H, d, J=7.6 Hz), 2.26 (3H, s), 2.21 (3H, s)

Mass spectrometric value (ESI-MS) 449, 451 (M−1)

Compound 500 Pyridin-2-carboxylic acid [4-bromo-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-amide

The title compound 500 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 8.63 (1H, s), 8.59 (1H, d, J=8.8 Hz), 8.24 (1H, s), 8.14 (1H, d, J=7.8 Hz), 7.97 (1H, s), 7.92 (1H, d, J=7.8 Hz), 7.78-7.84 (2H, m), 7.58 (1H, dd, J=2.2 Hz, J=9.0 Hz), 7.45 (1H, d, J=8.3 Hz), 7.38-7.43 (1H, m)

Mass spectrometric value (ESI-MS) 523, 525 (M−1)

Compound 501 N-[4-Bromo-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-4-ethoxy-benzamide

The title compound 501 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 8.52 (1H, d, J=8.8 Hz), 8.35 (1H, s), 7.99 (2H, d, J=8.5 Hz), 7.71 (1H, s), 7.51-7.60 (3H, m), 7.35-7.42 (1H, m), 7.09-7.15 (1H, m), 6.95-6.99 (2H, m), 4.10 (2H, q, J=7.0 Hz), 1.45 (3H, t, J=7.0 Hz)

Mass spectrometric value (ESI-MS) 482, 484 (M−1)

Compound 502 N-[4-Bromo-2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-4-ethoxy-benzamide

The title compound 502 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 8.53 (1H, d, J=9.0 Hz), 8.25 (1H, s), 7.92 (2H, d, J=8.8 Hz), 7.70-7.79 (3H, m), 7.55 (1H, dd, J=9.0 Hz, J=2.2 Hz), 7.00-7.09 (2H, m), 6.87-6.94 (2H, m), 4.04 (2H, q, J=7.0 Hz), 1.39 (3H, t, J=7.0 Hz)

Mass spectrometric value (ESI-MS) 482, 484 (M−1)

Compound 503 N-[4-Bromo-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-ethoxy-benzamide

The title compound 503 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 8.56 (1H, d, J=9.0 Hz), 8.31 (1H, s), 7.99 (2H, d, J=8.5 Hz), 7.71 (2H, s), 7.69 (1H, s), 7.53-7.59 (1H, m), 7.22 (2H, d, J=8.1 Hz), 6.96 (2H, d, J=8.8 Hz), 4.09 (2H, q, J=7.0 Hz), 2.38 (3H, s), 1.44 (3H, t, J=7.0 Hz)

Mass spectrometric value (ESI-MS) 478, 480 (M−1)

Compound 504 N-[4-Bromo-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-ethoxy-benzamide

The title compound 504 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 8.48 (1H, d, J=8.5 Hz), 8.33 (1H, s), 7.99 (2H, d, J=8.1 Hz), 7.69 (1H, s), 7.63 (1H, s), 7.45-7.56 (2H, m), 7.16 (1H, d, J=7.8 Hz), 6.92-6.98 (2H, m), 4.08 (2H, q, J=6.9 Hz), 2.29 (3H, s), 2.27 (3H, s), 1.44 (3H, t, J=6.8 Hz)

Mass spectrometric value (ESI-MS) 492, 494 (M−1)

Compound 505 Pyridin-2-carboxylic acid [2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-amide

The title compound 505 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 8.65-8.76 (2H, m), 8.20-8.28 (2H, m), 7.86-7.92 (1H, m), 7.65-7.72 (1H, m), 7.50-7.61 (3H, m), 7.43-7.50 (1H, m), 7.31-7.38 (1H, m), 7.10-7.20 (1H, m), 7.02-7.10 (1H, m)

Mass spectrometric value (ESI-MS) 361 (M−1)

Compound 506 Pyridin-2-carboxylic acid [2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-amide

The title compound 506 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 8.65-8.75 (2H, m), 8.20-8.28 (2H, m), 7.88 (1H, dd, J=1.7 Hz, J=7.7 Hz), 7.74-7.83 (2H, m), 7.63-7.70 (1H, m), 7.51-7.59 (1H, m), 7.43-7.49 (1H, m), 7.09-7.19 (1H, m), 7.06 (2H, dd, J=8.5 Hz, J=8.5 Hz)

Mass spectrometric value (ESI-MS) 361 (M−1)

Compound 507 Pyridin-2-carboxylic acid [2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-amide

The title compound 507 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 8.65-8.74 (2H, m), 8.23 (1H, d, J=7.6 Hz), 8.20 (1H, s), 7.87 (1H, ddd, J=1.7 Hz, J=7.7 Hz, J=7.7 Hz), 7.63-7.69 (1H, m), 7.57-7.63 (1H, m), 7.49-7.57 (1H, m), 7.42-7.49 (2H, m), 7.07-7.15 (2H, m), 2.26 (3H, s), 2.24 (3H, s)

Mass spectrometric value (ESI-MS) 371 (M−1)

Compound 508 Pyridin-2-carboxylic acid [2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-amide

The title compound 508 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 8.67-8.73 (2H, m), 8.29 (1H, s), 8.23 (1H, d, J=7.8 Hz), 7.96-8.05 (2H, m), 7.89 (1H, ddd, J=1.7 Hz, J=7.7 Hz, J=7.7 Hz), 7.70 (1H, d, J=7.1 Hz), 7.46-7.59 (3H, m), 7.11-7.18 (1H, m)

Mass spectrometric value (ESI-MS) 445 (M−1)

Compound 509 Cyclohexanecarboxylic acid [4-bromo-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-amide

The title compound 509 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 8.49 (1H, d, J=9.0 Hz), 8.22-8.29 (1H, m), 7.48-7.68 (3H, m), 7.35-7.44 (2H, m), 7.12-7.18 (1H, m), 2.27-2.36 (1H, m), 1.97-2.04 (2H, m), 1.79-1.87 (2H, m), 1.66-1.73 (1H, m), 1.45-1.52 (1H, m), 1.21-1.38 (4H, m)

Mass spectrometric value (ESI-MS) 444, 446 (M−1)

Compound 510 Isoxazole-5-carboxylic acid [4-bromo-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-amide

The title compound 510 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 8.59 (1H, d, J=8.8 Hz), 8.39 (1H, d, J=2.0 Hz), 8.31 (1H, s), 7.92 (1H, s), 7.63 (1H, dd, J=2.2 Hz, J=9.0 Hz), 7.51-7.59 (2H, m), 7.34-7.41 (1H, m), 7.07-7.13 (1H, m), 7.03 (1H, d, J=1.7 Hz)

Mass spectrometric value (ESI-MS) 429, 431 (M−1)

Compound 511 Isoxazole-5-carboxylic acid [4-bromo-2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-amide

The title compound 511 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 8.58 (1H, d, J=9.0 Hz), 8.39 (1H, d, J=2.0 Hz), 8.29 (1H, s), 7.93 (1H, d, J=1.7 Hz), 7.63-7.70 (2H, m), 7.55 (1H, d, J=7.8 Hz), 7.17-7.31 (2H, m), 7.03 (1H, d, J=1.7 Hz), 2.38 (3H, s)

Mass spectrometric value (ESI-MS) 425, 427 (M−1)

Compound 512 Isoxazole-5-carboxylic acid [4-bromo-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-amide

The title compound 512 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 8.59 (1H, d, J=8.8 Hz), 8.40 (1H, d, J=1.7 Hz), 8.26 (1H, s), 7.96 (1H, d, J=2.2 Hz), 7.68 (1H, dd, J=2.2 Hz, J=9.0 Hz), 7.63 (1H, s), 7.51 (1H, d, J=7.3 Hz), 7.18 (1H, d, J=7.8 Hz), 7.05 (1H, d, J=1.7 Hz), 2.30 (3H, s), 2.29 (3H, s)

Mass spectrometric value (ESI-MS) 439, 441 (M−1)

Compound 513 Isoxazole-5-carboxylic acid [4-bromo-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-amide

The title compound 513 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 8.60 (1H, d, J=9.0 Hz), 8.42 (1H, d, J=1.7 Hz), 8.35 (1H, s), 8.10 (1H, s), 8.04 (1H, d, J=8.3 Hz), 7.97-8.01 (1H, m), 7.70 (1H, dd, J=2.3 Hz, J=8.9 Hz), 7.58 (1H, d, J=8.3 Hz), 7.06 (1H, d, J=1.7 Hz)

Mass spectrometric value (ESI-MS) 513, 515 (M−1)

Compound 514 2,5-Dimethyl-furan-3-carboxylic acid [2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-amide

The title compound 514 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 8.56 (1H, d, J=8.5 Hz), 8.27 (1H, s), 7.46-7.68 (4H, m), 7.35-7.42 (1H, m), 7.04-7.14 (2H, m), 6.39 (1H, s), 2.62 (3H, s), 2.29 (3H, s)

Mass spectrometric value (ESI-MS) 378 (M−1)

Compound 515 2,5-Dimethyl-furan-3-carboxylic acid [2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-amide

The title compound 515 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 8.54 (1H, d, J=8.3 Hz), 8.27 (1H, s), 7.76-7.85 (2H, m), 7.61 (1H, d, J=7.6 Hz), 7.48 (1H, t, J=7.8 Hz), 7.01-7.16 (3H, m), 6.38 (1H, s), 2.62 (3H, s), 2.28 (3H, s)

Mass spectrometric value (ESI-MS) 378 (M−1)

Compound 516 2,5-Dimethyl-furan-3-carboxylic acid [2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-amide

The title compound 516 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 8.56 (1H, d, J=8.1 Hz), 8.27 (1H, s), 7.67-7.74 (1H, m), 7.40-7.60 (4H, m), 7.28-7.35 (1H, m), 6.96-7.04 (1H, m), 6.38 (1H, s), 2.64 (3H, s), 2.40 (3H, s), 2.29 (3H, s)

Mass spectrometric value (ESI-MS) 374 (M−1)

Compound 517 N-[3-(3-Fluoro-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-3,4-dimethoxy-benzamide

The title compound 517 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 8.15 (1H, s), 7.62-7.69 (2H, m), 7.58 (1H, d, J=9.3 Hz), 7.52 (1H, d, J=7.6 Hz), 7.37-7.44 (1H, m), 7.10-7.17 (1H, m), 6.93 (1H, d, J=8.3 Hz), 6.53 (1H, s), 3.98 (3H, s), 3.96 (3H, s), 2.60 (3H, s)

Mass spectrometric value (ESI-MS) 440 (M−1)

Compound 518 3,4-Dimethoxy-N-[4-methyl-3-(3-methyl-benzylidene-hydrazinocarbonyl)-thiophen-2-yl]-benzamide

The title compound 518 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 8.10 (1H, s), 7.63-7.72 (3H, m), 7.54 (1H, d, J=7.6 Hz), 7.24-7.35 (2H, m), 6.92 (1H, d, J=8.3 Hz), 6.53 (1H, s), 3.98 (3H, s), 3.96 (3H, s), 2.61 (3H, s), 2.40 (3H, s)

Mass spectrometric value (ESI-MS) 436 (M−1)

Compound 519 3,4-Dimethoxy-N-[4-methyl-3-(4-methyl-benzylidene-hydrazinocarbonyl)-thiophen-2-yl]-benzamide

The title compound 519 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 8.10 (1H, s), 7.63-7.73 (4H, m), 7.22-7.28 (2H, m), 6.92 (1H, d, J=8.1 Hz), 6.54 (1H, s), 3.98 (3H, s), 3.96 (3H, s), 2.61 (3H, s), 2.40 (3H, s)

Mass spectrometric value (ESI-MS) 436 (M−1)

Compound 521 N-[3-(3,4-Dimethyl-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-3,4-dimethoxy-benzamide

The title compound 521 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 8.07 (1H, s), 7.63-7.70 (3H, m), 7.47 (1H, d, J=8.5 Hz), 7.19 (1H, d, J=7.8 Hz), 6.92 (1H, d, J=8.5 Hz), 6.54 (1H, s), 3.98 (3H, s), 3.96 (3H, s), 2.61 (3H, s), 2.31 (6H, s)

Mass spectrometric value (ESI-MS) 450 (M−1)

Compound 522 N-[3-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-3,4-dimethoxy-benzamide

The title compound 522 was produced in the same manner as in Example 5.

¹H-NMR (CDCl₃, 400 MHz): δ 8.23 (1H, s), 8.05-8.08 (1H, m), 7.93-7.98 (1H, m), 7.62-7.68 (2H, m), 7.58 (1H, d, J=8.5 Hz), 6.92-7.68 (2H, m), 7.58 (1H, d, J=8.5 Hz), 6.92-6.97 (1H, m), 6.55 (1H, s), 3.98 (3H, s), 3.96 (3H, s), 2.61 (3H, s)

Mass spectrometric value (ESI-MS) 524 (M−1)

Compound 523 N-[2-(3,4-Dimethyl-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-3-yl]-3-(1H-[1,2,4]triazol-3-ylsulfanylmethyl)-benzamide

The title compound 523 was produced in the same manner as in Example 5.

Mass spectrometric value (ESI-MS) 503 (M−1)

Compound 524 N-[2-(3-Fluoro-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-3-yl]-3-(1H-[1,2,4]triazol-3-ylsulfanylmethyl)-benzamide

The title compound 524 was produced in the same manner as in Example 5.

Mass spectrometric value (ESI-MS) 493 (M−1)

Compound 525 N-[2-(3,4-Dimethyl-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-3-yl]-3-(3-hydroxy-propylsulfanylmethyl)-benzamide

The title compound 525 was produced in the same manner as in Example 5.

Mass spectrometric value (ESI-MS) 494 (M−1)

Compound 526 3-(3-Hydroxy-propylsulfanylmethyl)-N-[4-methyl-2-(4-methyl-benzylidene-hydrazinocarbonyl)-thiophen-3-yl]-benzamide

The title compound 526 was produced in the same manner as in Example 5.

Mass spectrometric value (ESI-MS) 480 (M−1)

Compound 527 N-[2-(3-Fluoro-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-3-yl]-3-(3-hydroxy-propylsulfanylmethyl)-benzamide

The title compound 527 was produced in the same manner as in Example 5.

Mass spectrometric value (ESI-MS) 484 (M−1)

Compound 528 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[2-(4-fluoro-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-3-yl]-benzamide

The title compound 528 was produced in the same manner as in Example 5.

Mass spectrometric value (ESI-MS) 522 (M−1)

Compound 529 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[2-(3-fluoro-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-3-yl]-benzamide

The title compound 529 was produced in the same manner as in Example 5.

Mass spectrometric value (ESI-MS) 522 (M−1)

Compound 530 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[2-(4-methoxy-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-3-yl]-benzamide

The title compound 530 was produced in the same manner as in Example 5.

Mass spectrometric value (ESI-MS) 534 (M−1)

Compound 531 3-[1,4′]Bipiperidinyl-1′-ylmethyl-N-[2-(4-methoxy-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-3-yl]-benzamide

The title compound 531 was produced in the same manner as in Example 5.

Mass spectrometric value (ESI-MS) 572 (M−1)

Compound 532 N-[2-(3,4-Dimethyl-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-3-yl]-3-[4-(2-hydroxy-ethyl)-piperazin-1-ylmethyl]-benzamide

The title compound 532 was produced in the same manner as in Example 5.

Mass spectrometric value (ESI-MS) 532 (M−1)

Compound 533 3-[4-(2-Hydroxy-ethyl)-piperazin-1-ylmethyl]-N-[4-methyl-2-(4-methyl-benzylidene-hydrazinocarbonyl)-thiophen-3-yl]-benzamide

The title compound 533 was produced in the same manner as in Example 5.

Mass spectrometric value (ESI-MS) 518 (M−1)

Compound 534 N-[2-(4-Fluoro-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-3-yl]-3-[4-(2-hydroxy-ethyl)-piperazin-1-ylmethyl]-benzamide

The title compound 534 was produced in the same manner as in Example 5.

Mass spectrometric value (ESI-MS) 522 (M−1)

Compound 535 N-[2-(3-Fluoro-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-3-yl]-3-[4-(2-hydroxy-ethyl)-piperazin-1-ylmethyl]-benzamide

The title compound 535 was produced in the same manner as in Example 5.

Mass spectrometric value (ESI-MS) 522 (M−1)

Compound 536 3-[(2-Diethylamino-ethylamino)-methyl]-N-[2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-3-yl]-benzamide

The title compound 536 was produced in the same manner as in Example 5.

Mass spectrometric value (ESI-MS) 518 (M−1)

Compound 537 3-[(2-Diethylamino-ethylamino)-methyl]-N-[4-methyl-2-(4-methyl-benzylidene-hydrazinocarbonyl)-thiophen-3-yl]-benzamide

The title compound 537 was produced in the same manner as in Example 5.

Mass spectrometric value (ESI-MS) 504 (M−1)

Compound 538 3-[(2-Diethylamino-ethylamino)-methyl]-N-[2-(3-fluoro-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-3-yl]-benzamide

The title compound 538 was produced in the same manner as in Example 5.

Mass spectrometric value (ESI-MS) 508 (M−1)

Compound 539 N-[2-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-3-yl]-3-[(2-diethylamino-ethylamino)-methyl]-benzamide

The title compound 539 was produced in the same manner as in Example 5.

Mass spectrometric value (ESI-MS) 592 (M−1)

Compound 540 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[4-methyl-2-(4-methyl-benzylidene-hydrazinocarbonyl)-thiophen-3-yl]-benzamide

The title compound 540 was produced in the same manner as in Example 5.

Mass spectrometric value (ESI-MS) 521 (M−1)

Compound 541 N-[2-(3,4-Dimethyl-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-3-yl]-3-(4-hydroxy-piperidin-1-ylmethyl)-benzamide

The title compound 541 was produced in the same manner as in Example 5.

Mass spectrometric value (ESI-MS) 503 (M−1)

Compound 542 N-[2-(3-Fluoro-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-3-yl]-3-(4-hydroxy-piperidin-1-ylmethyl)-benzamide

The title compound 542 was produced in the same manner as in Example 5.

Mass spectrometric value (ESI-MS) 493 (M−1)

Compound 543 3-(4-Hydroxy-piperidin-1-ylmethyl)-N-[2-(4-methoxy-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-3-yl]-benzamide

The title compound 543 was produced in the same manner as in Example 5.

Mass spectrometric value (ESI-MS) 505 (M−1)

Compound 544 Pyridin-2-carboxylic acid {4-bromo-2-[N′-(4-methyl-benzyl)-hydrazinocarbonyl]-phenyl}-amide

The title compound 544 was produced in the same manner as in Example 7.

Mass spectrometric value (ESI-MS) 439 (M−1)

Compound 545 N-{2-[N′-(4-Methyl-benzyl)-hydrazinocarbonyl]-phenyl}-isonicotinamide

The title compound 545 was produced in the same manner as in Example 7.

Mass spectrometric value (ESI-MS) 359 (M−1)

Compound 546 N-{4-Bromo-2-[N′-(4-chloro-3-trifluoromethyl-benzyl)-hydrazinocarbonyl]-phenyl}-3-(2-hydroxy-ethylsulfanylmethyl)-benzamide

The title compound 546 was produced in the same manner as in Example 7.

Mass spectrometric value (ESI-MS) 614, 616, 617 (M−1)

Compound 547 N-{4-Chloro-2-[N′-(4-methyl-benzyl)-hydrazinocarbonyl]-phenyl}-3-(2-hydroxy-ethylsulfanylmethyl)-benzamide

The title compound 547 was produced in the same manner as in Example 7.

Mass spectrometric value (ESI-MS) 483 (M−1)

Compound 548 N-{4-Bromo-2-[N′-(3,4-dimethyl-benzyl)-hydrazinocarbonyl]-phenyl}-3,4-dimethoxy-benzamide

The title compound 548 was produced in the same manner as in Example 7.

Mass spectrometric value (ESI-MS) 508, 510 (M−1)

Compound 549 3-{[Bis-(2-hydroxy-ethyl)-amino]-methyl}-N-[4-chloro-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 549 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.66 (1H, d, J=9.0 Hz), 8.35 (1H, s), 8.07 (1H, s), 7.93-7.96 (1H, m), 7.85-7.96 (1H, m), 7.85-7.92 (1H, m), 7.71-7.76 (1H, m), 7.58-7.65 (3H, m), 7.40-7.54 (2H, m), 7.15-7.23 (1H, m), 3.83 (2H, s), 3.61-3.67 (4H, m), 2.67-2.74 (4H, m)

Mass spectrometric value (ESI-MS) 511, 513 (M−1)

Compound 550 3-{[Bis-(2-hydroxy-ethyl)-amino]-methyl}-N-[4-chloro-2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 550 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.66 (1H, d, J=8.8 Hz), 8.35 (1H, s), 8.06 (1H, s), 7.87-7.95 (4H, m), 7.63 (1H, d, J=8.8 Hz), 7.62 (1H, d, J=8.8 Hz), 7.50 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.19 (2H, dd, J=8.8 Hz), 3.83 (2H, s), 3.65 (4H, t, J=5.9 Hz), 2.71 (4H, t, J=5.9 Hz)

Mass spectrometric value (ESI-MS) 511, 513 (M−1)

Example 8

Compound 551 N-[3-(3,4-Dimethyl-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-3-(1H-[1,2,4]triazol-3-ylsulfanylmethyl)-benzamide

Ethyl 2-amino-4-methylthiophene-3-carboxylate (compound A) (3.0 g) was dissolved in anhydrous methylene chloride (40.0 ml). Subsequently, pyridine (1.5 ml) and 3-(chloromethyl)benzoyl chloride (compound B) (2.8 ml) were added to the solution, and the mixuture was stirred at 0° C. for one hr. After the completion of the reaction, distilled water was added, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated to give 2-(3-chloromethyl-benzoylamino-4-methyl-thiophene-3-carboxylic acid ethyl ester as a useful intermediate (3.80 g, yield 70%).

2-(3-Chloromethyl-benzoylamino-4-methyl-thiophene-3-carboxylic acid ethyl ester (700 mg) obtained by the above reaction was dissolved in anhydrous methylene chloride (5.0 ml), triethylamine (580 μl) and 3-mercapto-1,2,4-triazole (compound B′) (404 mg) were added to the solution at room temperature, and the mixture was stirred at room temperature for 15 hr. After the completion of the reaction, water was added at room temperature, and the reaction mixture was extracted by liquid separation using chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated. The residue was purified by column chromatography eluted with a chloroform-methanol system to give 4-methyl-2-[3 (1H-[1,2,4]triazol-3-ylsulfanylmethyl)-benzoylamino]-thiophene-3-carboxylic acid ethyl ester as a useful intermediate (606 mg, yield 72%).

4-Methyl-2-[3 (1H-[1,2,4]triazol-3-ylsulfanylmethyl)-benzoylamino]-thiophene-3-carboxylic acid ethyl ester produced by the above reaction was dissolved in ethanol (5.0 ml), hydrazine monohydrate (650 μl) was added to the solution, and the mixture was heated under reflux with stirring for 15 hr. After the completion of the reaction, water was added thereto at room temperature, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated to give a hydrazine compound N-(3-hydrazinocarbonyl-4-methyl-thiophen-2-yl)-3-(1H-[1,2,4]triazol-3-ylsulfanylmethyl)-benzamide (103 mg, crude yield 20%).

N-(3-Hydrazinocarbonyl-4-methyl-thiophen-2-yl)-3-(1H-[1,2,4]triazol-3-ylsulfanylmethyl)-benzamide (20 mg) was dissolved in anhydrous toluene (1.0 ml), 3,4-dimethylbenzaldehyde (compound C) (13.0 μl) was added to the solution at room temperature, and the mixture was heated under reflux with stirring for 15 hr. After the completion of the reaction, the reaction product was purified by column chromatography eluted with a chloroform-methanol system to give the title compound 551 (17.4 mg, yield 69%).

¹H-NMR (DMSO-d₆, 400 MHz): δ 2.25 (6H, s), 2.37 (3H, s), 4.40 (2H, s), 6.79 (1H, s), 7.15-8.00 (7H, m), 8.28 (1H, s), 8.56 (1H, s), 11.20-11.70 (2H, m), 14.05 (1H, s)

Mass spectrometric value (ESI-MS) 503 (M−1)

Compound 552 N-[4-Methyl-3-(4-methyl-benzylidene-hydrazinocarbonyl)-thiophen-2-yl]-3-(1H-[1,2,4]triazol-3-ylsulfanylmethyl)-benzamide

The title compound 552 was produced in substantially the same manner as in Example 8.

¹H-NMR (DMSO-d₆, 400 MHz): δ 2.34 (3H, s), 2.37 (3H, s), 4.40 (2H, s), 6.80 (1H, s), 7.20-8.00 (8H, m), 8.30 (1H, m), 8.57 (1H, s), 11.30-11.70 (2H, m), 14.10 (1H, s)

Mass spectrometric value (ESI-MS) 489 (M−1)

Compound 553 N-[3-(4-Fluoro-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-3-(1H-[1,2,4]triazol-3-ylsulfanylmethyl)-benzamide

The title compound 553 was produced in substantially the same manner as in Example 8.

¹H-NMR (DMSO-d₆, 400 MHz): δ 2.36 (3H, s), 4.40 (2H, s), 6.81 (1H, s), 7.25-8.00 (8H, m), 8.40 (1H, m), 8.57 (1H, s), 11.30-11.70 (2H, m), 14.05 (1H, s)

Mass spectrometric value (ESI-MS) 493 (M−1)

Compound 554 N-[3-(3-Fluoro-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-3-(1H-[1,2,4]triazol-3-ylsulfanylmethyl)-benzamide

The title compound 554 was produced in substantially the same manner as in Example 8.

¹H-NMR (DMSO-d₆, 400 MHz): δ 2.35 (3H, s), 4.40 (2H, s), 6.81 (1H, s), 7.20-7.96 (8H, m), 8.36 (1H, s), 8.56 (1H, s), 11.40-11.75 (2H, m), 14.05 (1H, s)

Mass spectrometric value (ESI-MS) 493 (M−1)

Compound 555 N-[3-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-3-(1H-[1,2,4]triazol-3-ylsulfanylmethyl)-benzamide

The title compound 555 was produced in substantially the same manner as in Example 8.

¹H-NMR (DMSO-d₆, 400 MHz): δ 2.34 (3H, s), 4.38 (2H, s), 6.82 (1H, s), 7.40-8.58 (9H, m), 11.40-11.75 (2H, m), 14.05 (1H, s)

Mass spectrometric value (ESI-MS) 577 (M−1)

Compound 556 N-[3-(4-Methoxy-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-3-(1H-[1,2,4]triazol-3-ylsulfanylmethyl)-benzamide

The title compound 556 was produced in substantially the same manner as in Example 8.

¹H-NMR (DMSO-d₆, 400 MHz): δ 2.37 (3H, s), 3.80 (3H, s), 4.40 (2H, s), 6.80 (1H, s), 7.01 (2H, m), 7.40-7.74 (6H, m), 8.35 (1H, s), 8.57 (1H, s), 11.20-11.75 (2H, m), 14.05 (1H, s)

Mass spectrometric value (ESI-MS) 505 (M−1)

Compound 557 N-[3-(3,4-Dimethyl-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-3-(3-hydroxy-propylsulfanylmethyl)-benzamide

The title compound 557 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.77 (2H, m), 2.31 (6H, m), 2.50 (5H, m), 3.63 (2H, m), 3.82 (2H, s), 6.70 (1H, s), 7.19 (1H, d, J=7.8 Hz), 7.45-7.67 (4H, m), 7.80-7.95 (2H, m), 8.22 (1H, s)

Mass spectrometric value (ESI-MS) 494 (M−1)

Compound 558 3-(3-Hydroxy-propylsulfanylmethyl)-N-[4-methyl-3-(4-methyl-benzylidene-hydrazinocarbonyl)-thiophen-2-yl]-benzamide

The title compound 558 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.77 (2H, m), 2.38 (3H, s), 2.50 (5H, m), 3.60 (2H, t, J=6.4 Hz), 3.82 (2H, s), 6.71 (1H, d, J=0.96 Hz), 7.26 (2H, d, J=7.6 Hz), 7.50 (1H, m), 7.60 (1H, m), 7.73 (2H, m), 7.84 (1H, m), 7.92 (1H, s), 8.26 (1H, s)

Mass spectrometric value (ESI-MS) 480 (M−1)

Compound 559 N-[3-(4-Fluoro-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-3-(3-hydroxy-propylsulfanylmethyl)-benzamide

The title compound 559 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.77 (2H, m), 2.50 (5H, m), 3.62 (2H, m), 3.82 (2H, s), 6.71 (1H, s), 7.12 (2H, m), 7.50 (1H, m), 7.60 (1H, m), 7.87 (4H, m), 8.28 (1H, s)

Mass spectrometric value (ESI-MS) 484 (M−1)

Compound 560 N-[3-(3-Fluoro-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-3-(3-hydroxy-propylsulfanylmethyl)-benzamide

The title compound 560 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.77 (2H, m), 2.51 (5H, m), 3.60 (2H, t, J=6.2 Hz), 3.82 (2H, s), 6.72 (1H, s), 7.18 (1H, m), 7.42-7.65 (5H, m), 7.84 (1H, s), 7.93 (1H, s), 8.29 (1H, s)

Mass spectrometric value (ESI-MS) 484 (M−1)

Compound 561 N-[3-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-3-(3-hydroxy-propylsulfanylmethyl)-benzamide

The title compound 561 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.77 (2H, m), 2.50 (5H, m), 3.60 (2H, t, J=6.1 Hz), 3.82 (2H, s), 6.72 (1H, s), 7.50 (1H, m), 7.61 (1H, d, J=7.3 Hz), 7.68 (1H, d, J=8.3 Hz), 7.84 (1H, m), 7.93 (1H, s), 8.05 (1H, m), 8.33 (2H, s)

Mass spectrometric value (ESI-MS) 568 (M−1)

Compound 562 3-(3-Hydroxy-propylsulfanylmethyl)-N-[3-(4-methoxy-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-benzamide

The title compound 562 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.77 (2H, m), 2.50 (5H, m), 3.60 (2H, t, J=6.2 Hz), 3.81 (2H, s), 3.84 (3H, s), 6.70 (1H, d, J=1.0 Hz), 6.99 (2H, d, J=8.3 Hz), 7.50 (1H, m), 7.60 (1H, m), 7.80 (3H, m), 7.92 (1H, s), 8.23 (1H, m)

Mass spectrometric value (ESI-MS) 496 (M−1)

Compound 563 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[3-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-benzamide

The title compound 563 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.05 (6H, t, J=7.2 Hz), 2.26 (3H, s), 2.30 (3H, s), 2.31 (3H, s), 2.50 (2H, m), 2.57 (2H, m), 2.67 (5H, m), 2.79 (2H, m), 3.65 (2H, s), 6.64 (1H, s), 7.19 (1H, d, J=7.8 Hz), 7.46-7.65 (4H, m), 7.86-7.97 (2H, m), 8.21 (1H, s)

Mass spectrometric value (ESI-MS) 532 (M−1)

Compound 564 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[4-methyl-3-(4-methyl-benzylidene-hydrazinocarbonyl)-thiophen-2-yl]-benzamide

The title compound 564 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.05 (6H, t, J=7.3 Hz), 2.26 (3H, s), 2.38 (3H, s), 2.50 (2H, s), 2.57 (2H, m), 2.67 (5H, m), 2.78 (2H, m), 3.65 (2H, s), 6.63 (1H, s), 7.25 (2H, d, J=7.8 Hz), 7.51 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.58 (1H, d, J=7.6 Hz), 7.72 (2H, m), 7.91 (2H, m), 8.25 (1H, s)

Mass spectrometric value (ESI-MS) 518 (M−1)

Compound 565 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[3-(4-fluoro-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-benzamide

The title compound 565 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.05 (6H, m), 2.56 (3H, s), 2.49 (2H, m), 2.57 (2H, m), 2.66 (5H, m), 2.77 (2H, m), 3.64 (2H, s), 6.62 (1H, s), 7.16 (2H, dd, J=8.7 Hz, J=8.7 Hz), 7.50 (2H, m), 7.91 (4H, m), 8.27 (1H, s)

Mass spectrometric value (ESI-MS) 522 (M−1)

Compound 566 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[3-(3-fluoro-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-benzamide

The title compound 566 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.07 (6H, t, J=7.2 Hz), 2.26 (3H, m), 2.50 (2H, s), 2.58 (2H, m), 2.72 (5H, m), 2.83 (2H, m), 3.65 (2H, s), 6.62 (1H, s), 7.15 (1H, ddd, J=8.3 Hz, J=8.3 Hz, J=1.7 Hz), 7.40-7.80 (5H, m), 7.87-7.90 (2H, m), 8.27 (1H, s)

Mass spectrometric value (ESI-MS) 522 (M−1)

Compound 567 N-[3-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-3-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 567 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.06 (6H, t, J=7.3 Hz), 2.26 (3H, m), 2.49 (2H, s), 2.57 (2H, m), 2.68 (5H, m), 2.80 (2H, m), 3.64 (2H, s), 6.60 (1H, s), 7.50 (1H, m), 7.57 (1H, d, J=7.6 Hz), 7.65 (1H, d, J=8.3 Hz), 7.94 (3H, m), 8.28 (2H, m)

Mass spectrometric value (ESI-MS) 606 (M−1)

Compound 568 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[3-(4-methoxy-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-benzamide

The title compound 568 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.05 (6H, t, J=7.2 Hz), 2.25 (3H, s), 2.49 (2H, s), 2.57 (2H, m), 2.66 (5H, m), 2.77 (2H, m), 3.64 (2H, m), 3.83 (3H, s), 6.63 (1H, s), 6.97 (2H, d, J=8.5 Hz), 7.42-7.59 (2H, m), 7.76 (2H, m), 7.90 (2H, m), 8.22 (1H, s)

Mass spectrometric value (ESI-MS) 534 (M−1)

Compound 569 3-[1,4′]Bipiperidinyl-1′-ylmethyl-N-[3-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-benzamide

The title compound 569 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.49 (2H, m), 1.64 (6H, m), 1.87 (2H, m), 2.03 (2H, m), 2.27 (1H, m), 2.29 (6H, m), 2.49 (3H, s), 2.71 (4H, m), 2.96 (2H, d, J=11.0 Hz), 3.59 (2H, s), 6.66 (1H, s), 7.18 (1H, d, J=7.6 Hz), 7.45-7.73 (4H, m), 7.88 (2H, s), 8.22 (1H, s)

Mass spectrometric value (ESI-MS) 570 (M−1)

Compound 570 3-[1,4′]Bipiperidinyl-1′-ylmethyl-N-[4-methyl-3-(4-methyl-benzylidene-hydrazinocarbonyl)-thiophen-2-yl]-benzamide

The title compound 570 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.49 (2H, m), 1.65 (6H, m), 1.88 (2H, d, J=11.0 Hz), 2.04 (2H, t, J=11.5 Hz), 2.34 (1H, s), 2.37 (3H, s), 2.49 (3H, s), 2.74 (4H, bs), 2.97 (2H, d, J=11.2 Hz), 3.58 (2H, s), 6.67 (1H, s), 7.24 (2H, d, J=7.8 Hz), 7.45-7.60 (2H, m), 7.70 (2H, m), 7.85-7.95 (2H, m), 8.26 (1H, s)

Mass spectrometric value (ESI-MS) 556 (M−1)

Compound 571 3-[1,4′]Bipiperidinyl-1′-ylmethyl-N-[3-(4-fluoro-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-benzamide

The title compound 571 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.48 (2H, m), 1.63 (6H, m), 1.86 (2H, d, J=11.4 Hz), 2.03 (2H, t, J=11.2 Hz), 2.36-2.54 (4H, m), 2.66 (4H, m), 2.96 (2H, d, J=11.2 Hz), 3.58 (2H, s), 6.66 (1H, s), 7.17 (2H, dd, J=8.5 Hz, J=8.5 Hz), 7.45-7.60 (2H, m), 7.85-7.94 (4H, m), 8.28 (1H, s)

Mass spectrometric value (ESI-MS) 560 (M−1)

Compound 572 3-[1,4′]Bipiperidinyl-1′-ylmethyl-N-[3-(3-fluoro-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-benzamide

The title compound 572 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.49 (2H, m), 1.64 (6H, m), 1.87 (2H, d, J=11.7 Hz), 2.03 (2H, t, J=11.2 Hz), 2.49 (4H, s), 2.72 (4H, m), 2.96 (2H, d, J=11.5 Hz), 3.58 (2H, s), 6.65 (1H, s), 7.15 (1H, m), 7.40-7.75 (5H, m), 7.85-7.95 (2H, m), 8.28 (1H, s)

Mass spectrometric value (ESI-MS) 560 (M−1)

Compound 573 3-[1,4′]Bipiperidinyl-1′-ylmethyl-N-[3-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-benzamide

The title compound 573 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.49 (2H, m), 1.63 (6H, m), 1.87 (2H, d, J=11.2 Hz), 2.04 (2H, t, J=11.1 Hz), 2.40-2.54 (4H, m), 2.68 (4H, m), 2.97 (2H, d, J=11.5 Hz), 3.59 (2H, s), 6.65 (1H, s), 7.45-7.60 (2H, m), 7.67 (1H, d, J=8.3 Hz), 7.85-8.05 (3H, m), 8.31 (2H, m)

Mass spectrometric value (ESI-MS) 644 (M−1)

Compound 574 3-[1,4′]Bipiperidinyl-1′-ylmethyl-N-[3-(4-methoxy-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-benzamide

The title compound 574 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.49 (2H, m), 1.61 (6H, m), 1.85 (2H, d, J=11.7 Hz), 2.02 (2H, t, J=11.6 Hz), 2.30-2.52 (4H, m), 2.65 (4H, bs), 2.95 (2H, d, J=11.0 Hz), 3.58 (2H, s), 3.83 (3H, s), 6.66 (1H, s), 6.98 (2H, d, J=8.3 Hz), 7.44-7.61 (2H, m), 7.76 (2H, m), 7.90 (2H, m), 8.23 (1H, s)

Mass spectrometric value (ESI-MS) 572 (M−1)

Compound 575 N-[3-(3,4-Dimethyl-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-3-[4-(2-hydroxy-ethyl)-piperazin-1-ylmethyl]-benzamide

The title compound 575 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 2.29 (6H, s), 2.48 (3H, s), 2.52-2.70 (10H, m), 3.62 (2H, s), 3.66 (2H, t, J=6.0 Hz), 6.68 (1H, d, J=1.0 Hz), 7.17 (1H, d, J=7.6 Hz), 7.50 (2H, m), 7.59 (2H, m), 7.80-7.95 (2H, m), 8.22 (1H, s)

Mass spectrometric value (ESI-MS) 532 (M−1)

Compound 576 3-[4-(2-Hydroxy-ethyl)-piperazin-1-ylmethyl]-N-[4-methyl-3-(4-methyl-benzylidene-hydrazinocarbonyl)-thiophen-2-yl]-benzamide

The title compound 576 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 2.38 (3H, s), 2.49 (3H, s), 2.54-2.74 (10H, m), 3.60-3.70 (4H, m), 6.71 (1H, d, J=1.2 Hz), 7.25 (2H, d, J=7.6 Hz), 7.51 (1H, dd, J=7.4 Hz, J=7.4 Hz), 7.59 (1H, d, J=7.4 Hz), 7.71 (2H, bs), 7.85-7.95 (2H, m), 8.26 (1H, s)

Mass spectrometric value (ESI-MS) 518 (M−1)

Compound 577 N-[3-(4-Fluoro-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-3-[4-(2-hydroxy-ethyl)-piperazin-1-ylmethyl]-benzamide

The title compound 577 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 2.49 (3H, m), 2.52-2.76 (10H, m), 3.63 (2H, s), 3.68 (2H, t, J=5.8 Hz), 6.69 (1H, d, J=1.0 Hz), 7.17 (2H, dd, J=8.6 Hz, J=8.6 Hz), 7.50 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.59 (1H, d, J=7.6 Hz), 7.82-7.94 (4H, m), 8.28 (1H, s)

Mass spectrometric value (ESI-MS) 522 (M−1)

Compound 578 N-[3-(3-Fluoro-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-3-[4-(2-hydroxy-ethyl)-piperazin-1-ylmethyl]-benzamide

The title compound 578 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 2.49 (3H, s), 2.57 (4H, m), 2.64 (2H, t, J=5.9 Hz), 2.71 (4H, m), 3.63 (2H, s), 3.68 (2H, t, J=5.9 Hz), 6.68 (1H, d, J=1.0 Hz), 7.16 (1H, dd, J=8.1 Hz, J=8.1 Hz), 7.40-7.70 (5H, m), 7.82-7.95 (2H, m), 8.28 (1H, s)

Mass spectrometric value (ESI-MS) 522 (M−1)

Compound 579 N-[3-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-3-[4-(2-hydroxy-ethyl)-piperazin-1-ylmethyl]-benzamide

The title compound 579 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 2.49 (3H, s), 2.52-2.68 (10H, m), 3.63 (2H, s), 3.66 (2H, t, J=6.0 Hz), 6.70 (1H, d, J=1.0 Hz), 7.51 (1H, dd, J=7.3 Hz, J=7.3 Hz), 7.60 (1H, d, J=7.3 Hz), 7.67 (1H, d, J=8.3 Hz), 7.87 (1H, m), 7.93 (1H, s), 8.00 (1H, bs), 8.32 (2H, m)

Mass spectrometric value (ESI-MS) 606 (M−1)

Compound 580 3-[4-(2-Hydroxy-ethyl)-piperazin-1-ylmethyl]-N-[3-(4-methoxy-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-benzamide

The title compound 580 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 2.49 (3H, s), 2.50-2.75 (10H, m), 3.63 (2H, s), 3.67 (2H, t, J=6.0 Hz), 3.83 (3H, s), 6.69 (1H, d, J=1.0 Hz), 6.98 (2H, d, J=8.3 Hz), 7.50 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.59 (1H, d, J=7.6 Hz), 7.76 (2H, m), 7.82-7.94 (2H, m), 8.23 (1H, s)

Mass spectrometric value (ESI-MS) 534 (M−1)

Compound 581 3-[(2-Diethylamino-ethylamino)-methyl]-N-[3-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-benzamide

The title compound 581 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.20 (6H, t, J=7.2 Hz), 2.31 (3H, s), 2.32 (3H, s), 2.51 (3H, s), 2.91 (2H, t, J=6.2 Hz), 3.02 (6H, m), 3.97 (2H, s), 6.71 (1H, d, J=1.0 Hz), 7.20 (1H, d, J=7.8 Hz), 7.50-7.70 (4H, m), 7.91 (1H, m), 7.99 (1H, m), 8.25 (1H, s)

Mass spectrometric value (ESI-MS) 518 (M−1)

Compound 582 3-[(2-Diethylamino-ethylamino)-methyl]-N-[4-methyl-3-(4-methyl-benzylidene-hydrazinocarbonyl)-thiophen-2-yl]-benzamide

The title compound 582 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.22 (6H, t, J=7.2 Hz), 2.39 (3H, s), 2.51 (3H, s), 2.93 (2H, t, J=6.2 Hz), 3.06 (6H, m), 3.39 (2H, s), 6.72 (1H, d, J=1.0 Hz), 7.27 (2H, d, J=7.8 Hz), 7.52-7.77 (4H, m), 7.91 (1H, m), 8.01 (1H, m), 8.28 (1H, s)

Mass spectrometric value (ESI-MS) 504 (M−1)

Compound 583 3-[(2-Diethylamino-ethylamino)-methyl]-N-[3-(4-fluoro-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-benzamide

The title compound 583 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.19 (6H, t, J=7.2 Hz), 2.52 (3H, s), 2.89 (2H, t, J=6.1 Hz), 2.98 (6H, m), 3.96 (2H, s), 6.72 (1H, d, J=1.0 Hz), 7.19 (2H, dd, J=8.7 Hz, J=8.7 Hz), 7.56 (1H, m), 7.64 (1H, d, J=7.2 Hz), 7.90 (3H, m), 7.99 (1H, s), 8.30 (1H, s)

Mass spectrometric value (ESI-MS) 509 (M−1)

Compound 584 3-[(2-Diethylamino-ethylamino)-methyl]-N-[3-(3-fluoro-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-benzamide

The title compound 584 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.20 (6H, t, J=7.2 Hz), 2.52 (3H, s), 2.90 (2H, m), 3.00 (6H, m), 3.96 (2H, s), 6.71 (1H, d, J=1.2 Hz), 7.18 (1H, dd, J=8.3 Hz, J=8.3 Hz), 7.46 (1H, m), 7.52-7.75 (4H, m), 7.91 (1H, m), 7.99 (1H, s), 8.31 (1H, s)

Mass spectrometric value (ESI-MS) 508 (M−1)

Compound 585 N-[3-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-3-[(2-diethylamino-ethylamino)-methyl]-benzamide

The title compound 585 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.16 (6H, t, J=7.2 Hz), 2.51 (3H, s), 2.91 (8H, m), 3.95 (2H, s), 6.70 (1H, d, J=1.2 Hz), 7.55 (1H, m), 7.64 (1H, d, J=8.0 Hz), 7.69 (1H, d, J=8.3 Hz), 7.91 (1H, m), 7.98 (2H, m), 8.34 (2H, s)

Mass spectrometric value (ESI-MS) 592 (M−1)

Compound 586 3-[(2-Diethylamino-ethylamino)-methyl]-N-[3-(4-methoxy-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-benzamide

The title compound 586 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.16 (6H, t, J=7.2 Hz), 2.51 (3H, s), 2.90 (8H, m), 3.85 (3H, s), 3.94 (2H, s), 6.70 (1H, d, J=1.0 Hz), 6.99 (2H, d, J=8.8 Hz), 7.56 (1H, m), 7.64 (1H, m), 7.79 (2H, d, J=7.3 Hz), 7.91 (1H, m), 7.98 (1H, s), 8.25 (1H, s)

Mass spectrometric value (ESI-MS) 520 (M−1)

Compound 587 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[3-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-benzamide

The title compound 587 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.09 (6H, m), 2.31 (6H, m), 2.51 (7H, m), 3.60-3.95 (4H, m), 6.70 (1H, d, J=1.0 Hz), 7.19 (1H, d, J=8.0 Hz), 7.52 (2H, m), 7.65 (2H, d, J=6.6 Hz), 7.87 (1H, m), 7.99 (1H, s), 8.22 (1H, s)

Mass spectrometric value (ESI-MS) 535 (M−1)

Compound 588 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[4-methyl-3-(4-methyl-benzylidene-hydrazinocarbonyl)-thiophen-2-yl]-benzamide

The title compound 588 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.09 (6H, m), 2.38 (3H, s), 2.51 (7H, m), 3.68-3.94 (4H, m), 6.70 (1H, d, J=1.2 Hz), 7.25 (2H, m), 7, 51 (1H, m), 7.65 (1H, d, J=7.3 Hz), 7.73 (2H, m), 7.87 (1H, m), 7.99 (1H, s), 8.26 (1H, s)

Mass spectrometric value (ESI-MS) 521 (M−1)

Compound 589 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[3-(4-fluoro-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-benzamide

The title compound 589 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.09 (6H, m), 2.49 (7H, m), 3.65-3.95 (4H, m), 6.71 (1H, m), 7.18 (2H, dd, J=8.8 Hz, J=8.8 Hz), 7.51 (1H, dd, J=7.4 Hz, J=7.4 Hz), 7.65 (1H, d, J=7.4 Hz), 7.88 (3H, m), 7.99 (1H, s), 8.29 (1H, s)

Mass spectrometric value (ESI-MS) 526 (M−1)

Compound 590 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[3-(3-fluoro-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-benzamide

The title compound 590 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.09 (6H, m), 2.49 (7H, m), 3.87 (4H, m), 6.71 (1H, d, J=1.0 Hz), 7.17 (2H, m), 7.40-7.75 (4H, m), 7.87 (1H, d, J=7.8 Hz), 8.00 (1H, s), 8.29 (1H, s)

Mass spectrometric value (ESI-MS) 525 (M−1)

Compound 591 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[3-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-benzamide

The title compound 591 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.08 (6H, m), 2.50 (7H, m), 3.65-3.95 (4H, m), 6.71 (1H, d, J=1.0 Hz), 7.51 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.66 (2H, m), 7.86 (1H, m), 8.02 (2H, m), 8.33 (2H, m)

Mass spectrometric value (ESI-MS) 609 (M−1)

Compound 592 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[3-(4-methoxy-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-benzamide

The title compound 592 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.09 (6H, d, J=6.1 Hz), 2.49 (7H, m), 3.85 (7H, m), 6.70 (1H, d, J=1.0 Hz), 6.99 (2H, d, J=8.3 Hz), 7.51 (1H, m), 7.65 (1H, d, J=7.6 Hz), 7.84 (3H, m), 7.99 (1H, s), 8.23 (1H, s)

Mass spectrometric value (ESI-MS) 537 (M−1)

Compound 593 N-[3-(3,4-Dimethyl-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-3-(4-hydroxy-piperidin-1-ylmethyl)-benzamide

The title compound 593 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.59 (2H, m), 1.85 (2H, m), 2.29 (8H, bs), 2.48 (3H, s), 2.84 (2H, m), 3.66 (3H, m), 6.68 (1H, d, J=1.0 Hz), 7.17 (1H, d, J=7.6 Hz), 7.52 (1H, m), 7.61 (2H, d, J=5.6 Hz), 7.89 (2H, m), 8.22 (1H, s)

Mass spectrometric value (ESI-MS) 503 (M−1)

Compound 594 3-(4-Hydroxy-piperidin-1-ylmethyl)-N-[4-methyl-3-(4-methyl-benzylidene-hydrazinocarbonyl)-thiophen-2-yl]-benzamide

The title compound 594 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.59 (2H, m), 1.86 (2H, m), 2.35 (5H, m), 2.49 (3H, s), 2.87 (2H, m), 3.67 (3H, m), 6.70 (1H, d, J=1.2 Hz), 7.25 (2H, d, J=7.8 Hz), 7.53 (1H, dd, J=7.3 Hz, J=7.3 Hz), 7.63 (1H, d, J=7.3 Hz), 7.71 (2H, m), 7.91 (2H, m), 8.26 (1H, s)

Mass spectrometric value (ESI-MS) 489 (M−1)

Compound 595 N-[3-(4-Fluoro-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-3-(4-hydroxy-piperidin-1-ylmethyl)-benzamide

The title compound 595 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.62 (2H, m), 1.87 (2H, m), 2.36 (2H, m), 2.49 (3H, s), 2.89 (2H, m), 3.66 (1H_{, m),} 3.74 (2H, s), 6.72 (1H, d, J=1.0 Hz), 7.18 (2H, dd, J=8.6 Hz, J=8.6 Hz), 7.54 (1H, m), 7.64 (1H, d, J=7.3 Hz), 7.91 (4H, m), 8.29 (1H, s)

Mass spectrometric value (ESI-MS) 493 (M−1)

Compound 596 N-[3-(3-Fluoro-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-3-(4-hydroxy-piperidin-1-ylmethyl)-benzamide

The title compound 596 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.60 (2H, m), 1.87 (2H, m), 2.35 (2H, m), 2.49 (3H, s), 2.88 (2H, m), 3.66 (1H, m), 3.72 (2H, s), 6.69 (1H, d, J=1.1 Hz), 7.16 (1H, dd, J=8.3 Hz, J=8.3 Hz), 7.44 (1H, m), 7.53 (2H, m), 7.63 (2H, m), 7.91 (2H, m), 8.28 (1H, s)

Mass spectrometric value (ESI-MS) 493 (M−1)

Compound 597 N-[3-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-3-(4-hydroxy-piperidin-1-ylmethyl)-benzamide

The title compound 597 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.61 (2H, m), 1.86 (2H, m), 2.37 (2H, m), 2.50 (3H, s), 2.90 (2H, m), 3.67 (1H, m), 3.74 (2H, s), 6.72 (1H, d, J=1.0 Hz), 7.55 (1H, dd, J=7.5 Hz, J=7.5 Hz), 7.66 (2H, m), 7.92 (3H, m), 8.33 (2H, m)

Mass spectrometric value (ESI-MS) 577 (M−1)

Compound 598 3-(4-Hydroxy-piperidin-1-ylmethyl)-N-[3-(4-methoxy-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-benzamide

The title compound 598 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.61 (2H, m), 1.87 (2H, m), 2.37 (2H, m), 2.49 (3H, s), 2.89 (2H, m), 3.66 (1H, m), 3.73 (2H, s), 3.84 (3H, s), 6.69 (1H, d, J=1.0 Hz), 6.97 (2H, d, J=8.3 Hz), 7.53 (1H, m), 7.62 (1H, m), 7.76 (2H, m), 7.90 (2H, m), 8.23 (1H, s)

Mass spectrometric value (ESI-MS) 505 (M−1)

Compound 599 N-[3-(3,4-Dimethyl-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-3-(4-hydroxymethyl-piperidin-1-ylmethyl)-benzamide

The title compound 599 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.29 (2H, m), 1.50 (1H, m), 1.75 (2H, d, J=11.5 Hz), 2.19 (2H, m), 2.30 (6H, s), 2.49 (3H, s), 2.99 (2H, d, J=10.8 Hz), 3.38 (2H, d, J=6.6 Hz), 3.73 (2H, s), 6.70 (1H, d, J=1.0 Hz), 7.19 (1H, d, J=7.6 Hz), 7.54 (2H, m), 7.62 (2H, m), 7.91 (2H, m), 8.22 (1H, s)

Mass spectrometric value (ESI-MS) 517 (M−1)

Compound 600 3-(4-Hydroxymethyl-piperidin-1-ylmethyl)-N-[4-methyl-3-(4-methyl-benzylidene-hydrazinocarbonyl)-thiophen-2-yl]-benzamide

The title compound 600 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.30 (2H, m), 1.50 (1H, m), 1.75 (2H, d, J=13.2 Hz), 2.22 (2H, t, J=11.5 Hz), 2.37 (3H, s), 2.48 (3H, s), 3.00 (2H, d, J=11.0 Hz), 3.38 (2H, d, J=6.3 Hz), 3.74 (2H, s), 6.68 (1H, d, J=1.0 Hz), 7.24 (2H, d, J=7.8 Hz), 7.52 (1H, dd, J=7.4 Hz, J=7.4 Hz), 7.62 (1H, d, J=7.4 Hz), 7.69 (2H, m), 7.90 (2H, m), 8.25 (1H, s)

Mass spectrometric value (ESI-MS) 503 (M−1)

Compound 601 N-[3-(4-Fluoro-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-3-(4-hydroxymethyl-piperidin-1-ylmethyl)-benzamide

The title compound 601 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.30 (2H, m), 1.50 (1H, m), 1.75 (2H, d, J=12.2 Hz), 2.22 (2H, t, J=11.4 Hz), 2.48 (3H, s), 3.01 (2H, d, J=11.2 Hz), 3.38 (2H, d, J=6.4 Hz), 3.73 (2H, s), 6.68 (1H, d, J=1.0 Hz), 7.16 (2H, dd, J=8.6 Hz, J=8.6 Hz), 7.52 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.62 (1H, d, J=7.6 Hz), 7.88 (4H, m), 8.28 (1H, s)

Mass spectrometric value (ESI-MS) 507 (M−1)

Compound 602 N-[3-(3-Fluoro-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-3-(4-hydroxymethyl-piperidin-1-ylmethyl)-benzamide

The title compound 602 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.31 (2H, m), 1.51 (1H, m), 1.76 (2H, d, J=11.5 Hz), 2.23 (2H, d, J=10.8 Hz), 2.45 (3H, s), 3.02 (2H, d, J=11.2 Hz), 3.39 (2H, d, J=6.3 Hz), 3.75 (2H, s), 6.69 (1H, d, J=1.0 Hz), 7.17 (1H, m), 7.44 (1H, m), 7.53 (2H, m), 7.63 (2H, m), 7.90 (2H, m), 8.28 (1H, s)

Mass spectrometric value (ESI-MS) 507 (M−1)

Compound 603 N-[3-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-3-(4-hydroxymethyl-piperidin-1-ylmethyl)-benzamide

The title compound 603 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.31 (2H, m), 1.51 (1H, m), 1.76 (2H, d, J=11.7 Hz), 2.21 (2H, t, J=11.5 Hz), 2.49 (3H, s), 3.01 (2H, d, J=11.5 Hz), 3.38 (2H, d, J=6.3 Hz), 3.74 (2H, s), 6.70 (1H, s), 7.54 (1H, dd, J=7.4 Hz), 7.65 (2H, m), 7.94 (3H, m), 8.31 (2H, m)

Mass spectrometric value (ESI-MS) 591 (M−1)

Compound 604 3-(4-Hydroxymethyl-piperidin-1-ylmethyl)-N-[3-(4-methoxy-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-benzamide

The title compound 604 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.29 (2H, m), 1.50 (1H, m), 1.75 (2H, d, J=12.2 Hz), 2.20 (2H, t, J=11.1 Hz), 2.47 (3H, s), 3.00 (2H, d, J=10.8 Hz), 3.38 (2H, d, J=6.4 Hz), 3.72 (2H, s), 3.83 (3H, s), 6.67 (1H, s), 6.96 (2H, d, J=8.3 Hz), 7.51 (1H, dd, J=7.4 Hz), 7.61 (1H, d, J=7.4 Hz), 7.75 (2H, d, J=6.4 Hz), 7.89 (2H, m), 8.23 (1H, m)

Mass spectrometric value (ESI-MS) 519 (M−1)

Compound 605 N-[3-(3,4-Dimethyl-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl]-3-(3-hydroxy-propylsulfanyl-methyl)-benzamide

The title compound 605 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.77 (2H, m), 1.89 (4H, m), 2.30 (6H, s), 2.51 (2H, t, J=7.2 Hz), 2.74 (2H, m), 2.85 (2H, m), 3.60 (2H, t, J=6.2 Hz), 3.82 (2H, s), 7.19 (1H, d, J=7.6 Hz), 7.51 (2H, m), 7.61 (2H, m), 7.87 (2H, m), 8.21 (1H, s)

Mass spectrometric value (ESI-MS) 534 (M−1)

Compound 606 N-[3-(4-Fluoro-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl]-3-(3-hydroxy-propylsulfanylmethyl)-benzamide

The title compound 606 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.77 (2H, m), 1.89 (4H, m), 2.51 (2H, t, J=7.3 Hz), 2.75 (2H, m), 2.86 (2H, m), 3.60 (2H, t, J=6.2 Hz), 3.82 (2H, s), 7.18 (2H, dd, J=8.8 Hz, J=8.8 Hz), 7.50 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.60 (1H, d, J=7.6 Hz), 7.87 (2H, m), 8, 06 (2H, m), 8.27 (1H, s)

Mass spectrometric value (ESI-MS) 524 (M−1)

Compound 607 N-[3-(3-Fluoro-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl]-3-(3-hydroxy-propylsulfanylmethyl)-benzamide

The title compound 607 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.77 (2H, m), 1.90 (4H, m), 2.51 (2H, t, J=7.3 Hz), 2.77 (2H, m), 2.86 (2H, bs), 3.63 (2H, m), 3.82 (2H, s), 7.17 (1H, dd, J=8.0 Hz, J=8.0 Hz), 7.55 (5H, m), 7.84 (1H, d, J=7.1 Hz), 7.92 (1H, s), 8.27 (1H, s)

Mass spectrometric value (ESI-MS) 524 (M−1)

Compound 608 N-[3-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl]-3-(3-hydroxy-propylsulfanylmethyl)-benzamide

The title compound 608 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.77 (2H, m), 1.90 (4H, m), 2.51 (2H, m), 2.76 (2H, m), 2.86 (2H, m), 3.60 (2H, m), 3.83 (2H, s), 7.52 (1H, m), 7.62 (1H, m), 7.68 (1H, m), 7.75-8.08 (4H, m), 8.32 (1H, s)

Mass spectrometric value (ESI-MS) 608 (M−1)

Compound 609 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[3-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl]-benzamide

The title compound 609 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.08 (6H, t, J=7.2 Hz), 1.85 (4H, m), 2.24 (3H, s), 2.29 (6H, s), 2.75 (12H, m), 3.62 (2H, s), 7.17 (1H, d, J=7.6 Hz), 7.44 (2H, dd, J=15.0 Hz, J=7.6 Hz), 7.55 (2H, d, J=7.6 Hz), 7.63 (2H, s), 7.95 (2H, m), 8.06 (1H, s)

Mass spectrometric value (ESI-MS) 572 (M−1)

Compound 610 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[3-(4-methyl-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo-[b]thiophen-2-yl]-benzamide

The title compound 610 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.08 (6H, t, J=7.1 Hz), 1.85 (4H, m), 2.24 (3H, s), 2.37 (3H, s), 2.74 (12H, m), 3.61 (2H, s), 7.20 (2H, d, J=8.0 Hz), 7.44 (1H, dd, J=15.9 Hz, J=8.1 Hz), 7.54 (1H, d, J=7.8 Hz), 7.66 (2H, d, J=8.0 Hz), 7.95 (2H, m), 8.12 (1H, s)

Mass spectrometric value (ESI-MS) 558 (M−1)

Compound 611 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[3-(4-fluoro-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo-[b]thiophen-2-yl]-benzamide

The title compound 611 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.10 (6H, t, J=7.3 Hz), 1.83 (4H, m), 2.24 (3H, s), 2.75 (12H, m), 3.61 (2H, s), 7.09 (2H, dd, J=8.6 Hz, J=8.6 Hz), 7.44 (1H, dd, J=15.1 Hz, J=7.6 Hz), 7.54 (1H, d, J=7.6 Hz), 7.76 (2H, m), 7.93 (2H, m), 8.16 (1H, s)

Mass spectrometric value (ESI-MS) 562 (M−1)

Compound 612 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[3-(3-fluoro-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo-[b]thiophen-2-yl]-benzamide

The title compound 612 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.11 (6H, t, J=7.2 Hz), 1.81 (4H, m), 2.23 (3H, s), 2.77 (12H, m), 3.61 (2H, s), 7.08 (1H, m), 7.31-7.59 (4H, m), 7.91 (2H, m), 8.21 (1H, s)

Mass spectrometric value (ESI-MS) 562 (M−1)

Compound 613 N-[3-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl]-3-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 613 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.10 (6H, m), 1.91 (4H, m), 2.25 (3H, s), 2.55-2.80 (12H, m), 3.63 (2H, s), 7.46 (1H, m), 7.57 (2H, d, 8.3 Hz), 7.94 (3H, m), 8.04 (1H, m), 8.23 (1H, s)

Mass spectrometric value (ESI-MS) 646 (M−1)

Compound 614 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[3-(4-methoxy-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo-[b]thiophen-2-yl]-benzamide

The title compound 614 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.04 (6H, t, J=7.1 Hz), 1.83 (4H, m), 2.23 (3H, s), 2.68 (12H, m), 3.60 (2H, s), 3.82 (3H, s), 6.89 (2H, d, J=8.8 Hz), 7.45 (1H, dd, J=15.4 Hz, J=7.6 Hz), 7.56 (1H, d, J=7.6 Hz), 7.70 (2H, d, J=8.8 Hz), 7.82-8.02 (2H, m), 8.09 (1H, s)

Mass spectrometric value (ESI-MS) 574 (M−1)

Compound 615 3-[1,4′]Bipiperidinyl-1′-ylmethyl-N-[3-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl]-benzamide

The title compound 615 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.46 (2H, bs), 1.68-2.06 (15H, m), 2.27 (6H, s), 2.60-3.02 (10H, m), 3.54 (2H, s), 7.14 (1H, m), 7.46 (3H, m), 7.60 (1H, s), 7.94 (2H, m), 8.11 (1H, s)

Mass spectrometric value (ESI-MS) 610 (M−1)

Compound 616 3-[1,4′]Bipiperidinyl-1′-ylmethyl-N-[3-(4-methyl-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl]-benzamide

The title compound 616 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.47 (2H, bs), 1.68-2.08 (14H, m), 2.37 (3H, s), 2.65-3.00 (11H, m), 3.54 (2H, s), 7.20 (2H, d, J=7.8 Hz), 7.45 (2H, m), 7.66 (2H, d, J=7.8 Hz), 7.90 (2H, m), 8.16 (1H, s)

Mass spectrometric value (ESI-MS) 596 (M−1)

Compound 617 3-[1,4′]Bipiperidinyl-1′-ylmethyl-N-[3-(4-fluoro-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl]-benzamide

The title compound 617 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.48 (2H, bs), 1.65-2.10 (14H, m), 2.74 (7H, m), 2.87 (2H, m), 2.94 (2H, m), 3.55 (2H, s), 7.10 (2H, dd, J=8.6 Hz, J=8.6 Hz), 7.46 (2H, m), 7.77 (2H, m), 7.92 (1H, d, J=7.6 Hz), 7.97 (1H, s), 8.18 (1H, s)

Mass spectrometric value (ESI-MS) 600 (M−1)

Compound 618 3-[1,4′]Bipiperidinyl-1′-ylmethyl-N-[3-(3-fluoro-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl]-benzamide

The title compound 618 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.48 (2H, bs), 1.70-2.08 (14H, m), 2.86 (11H, m), 3.55 (2H, s), 7.10 (1H, ddd, J=8.3 Hz, J=8.3 Hz, J=2.4 Hz), 7.50 (5H, m), 7.91 (1H, d, J=7.6 Hz), 7.97 (1H, s), 8.20 (1H, s)

Mass spectrometric value (ESI-MS) 600 (M−1)

Compound 619 3-[1,4′]Bipiperidinyl-1′-ylmethyl-N-[3-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl]-benzamide

The title compound 619 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.47 (2H, bs), 1.86 (14H, m), 2.84 (11H, m), 3.53 (2H, s), 7.48 (3H, m), 7.91 (3H, m), 8.01 (1H, s), 8.31 (1H, s)

Mass spectrometric value (ESI-MS) 684 (M−1)

Compound 620 3-[1,4′]Bipiperidinyl-1′-ylmethyl-N-[3-(4-methoxy-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl]-benzamide

The title compound 620 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.47 (2H, bs), 1.85 (14H, m), 2.82 (11H, m), 3.53 (2H, bs), 3.82 (3H, m), 6.90 (2H, m), 7.43 (2H, m), 7.69 (2H, d, J=7.1 Hz), 7.91 (2H, m), 8.15 (1H, s)

Mass spectrometric value (ESI-MS) 612 (M−1)

Compound 621 N-[3-(3,4-Dimethyl-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl]-3-[4-(2-hydroxy-ethyl)-piperazin-1-ylmethyl]-benzamide

The title compound 621 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.87 (4H, m), 2.29 (6H, s), 2.55 (10H, m), 2.72 (2H, m), 2.86 (2H, m), 3.60 (4H, m), 7.16 (1H, d, J=7.6 Hz), 7.43 (2H, m), 7.54 (1H, d, J=7.8 Hz), 7.62 (1H, s), 7.93 (1H, d, J=7.8 Hz), 8.00 (1H, s), 8.05 (1H, s)

Mass spectrometric value (ESI-MS) 572 (M−1)

Compound 622 3-[4-(2-Hydroxy-ethyl)-piperazin-1-ylmethyl]-N-[3-(4-methyl-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo-[b]thiophen-2-yl]-benzamide

The title compound 622 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.85 (4H, m), 2.37 (3H, s), 2.54 (10H, m), 2.71 (2H, m), 2.85 (2H, m), 3.60 (4H, m), 7.20 (2H, d, J=7.8 Hz), 7.43 (1H, dd, J=7.8 Hz, J=7.8 Hz), 7.54 (1H, d, J=7.8 Hz), 7.66 (2H, d, J=7.8 Hz), 7.92 (1H, d, J=7.8 Hz), 8.00 (1H, s), 8.10 (1H, s)

Mass spectrometric value (ESI-MS) 558 (M−1)

Compound 623 N-[3-(4-Fluoro-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl]-3-[4-(2-hydroxy-ethyl)-piperazin-1-ylmethyl]-benzamide

The title compound 623 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.87 (4H, m), 2.54 (10H, m), 2.73 (2H, m), 2.86 (2H, m), 3.60 (4H, m), 7.11 (2H, dd, J=8.7 Hz, J=8.7 Hz), 7.44 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.54 (1H, d, J=7.6 Hz), 7.79 (2H, m), 7.92 (1H, m), 8.00 (1H, s), 8.12 (1H, s)

Mass spectrometric value (ESI-MS) 562 (M−1)

Compound 624 N-[3-(3-Fluoro-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl]-3-[4-(2-hydroxy-ethyl)-piperazin-1-ylmethyl]-benzamide

The title compound 624 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.87 (4H, m), 2.54 (10H, m), 2.72 (2H, m), 2.84 (2H, m), 3.60 (4H, m), 7.11 (1H, ddd, J=8.3 Hz, J=8.3 Hz, J=2.4 Hz), 7.45 (5H, m), 7.92 (1H, d, J=7.6 Hz), 8.00 (1H, s), 8.14 (1H, s)

Mass spectrometric value (ESI-MS) 562 (M−1)

Compound 625 N-[3-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl]-3-[4-(2-hydroxy-ethyl)-piperazin-1-ylmethyl]-benzamide

The title compound 625 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.83 (4H, m), 2.53 (10H, m), 2.69 (2H, m), 2.82 (2H, m), 3.60 (4H, m), 7.44 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.54 (2H, d, J=8.3 Hz), 7.92 (2H, m), 7.98 (1H, s), 8.01 (1H, s), 8.22 (1H, s)

Mass spectrometric value (ESI-MS) 646 (M−1)

Compound 626 3-[4-(2-Hydroxy-ethyl)-piperazin-1-ylmethyl]-N-[3-(4-methoxy-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo-[b]thiophen-2-yl]-benzamide

The title compound 626 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.85 (4H, m), 2.53 (10H, m), 2.70 (2H, m), 2.84 (2H, m), 3.59 (4H, m), 3.83 (3H, s), 6.90 (2H, d, J=8.8 Hz), 7.42 (1H, dd, J=7.8 Hz, J=7.8 Hz), 7.53 (1H, d, J=7.8 Hz), 7.72 (2H, d, J=8.8 Hz), 7.92 (1H, d, J=7.8 Hz), 7.99 (1H, s), 8.07 (1H, s)

Mass spectrometric value (ESI-MS) 574 (M−1)

Compound 627 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[3-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo-[b]thiophen-2-yl]-benzamide

The title compound 627 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.14 (6H, m), 1.84 (4H, m), 2.25 (6H, m), 2.50 (2H, d, J=5.6 Hz), 2.62 (2H, m), 2.70 (2H, m), 2.83 (2H, m), 3.81-4.06 (4H, m), 7.08 (1H, m), 7.46 (3H, m), 7.60 (1H, s), 8.02 (2H, m), 8.20 (1H, bs)

Mass spectrometric value (ESI-MS) 575 (M−1)

Compound 628 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[3-(4-methyl-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo-[b]thiophen-2-yl]-benzamide

The title compound 628 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.13 (6H, m), 1.87 (4H, m), 2.37 (3H, m), 2.50 (2H, d, J=5.6 Hz), 2.62 (2H, m), 2.71 (2H, m), 2.84 (2H, m), 3.93 (4H, m), 7.16 (2H, m), 7.44 (2H, m), 7.70 (2H, m), 8.00 (2H, m), 8.22 (1H, bs)

Mass spectrometric value (ESI-MS) 561 (M−1)

Compound 629 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[3-(4-fluoro-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl]-benzamide

The title compound 629 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.12 (6H, t, J=6.1 Hz), 1.88 (4H, m), 2.50 (2H, m), 2.63 (2H, m), 2.73 (2H, m), 2.84 (2H, m), 3.94 (4H, m), 7.06 (2H, dd, J=8.6 Hz, J=8.6 Hz), 7.44 (2H, m), 7.85 (2H, m), 8.05 (2H, m), 8.25 (1H, d, J=6.8 Hz)

Mass spectrometric value (ESI-MS) 565 (M−1)

Compound 630 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[3-(3-fluoro-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl]-benzamide

The title compound 630 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.14 (6H, t, J=6.1 Hz), 1.84 (4H, m), 2.51 (2H, m), 2.66 (4H, m), 2.83 (2H, m), 3.95 (4H, m), 7.00 (1H, m), 7.23 (1H, m), 7.42 (3H, m), 7.72 (1H, m), 8.03 (1H, m), 8.18 (1H, s), 8.27 (1H, d, J=10.3 Hz)

Mass spectrometric value (ESI-MS) 565 (M−1)

Compound 631 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[3-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl]-benzamide

The title compound 631 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.12 (6H, m), 1.72 (4H, m), 2.52 (2H, d, J=6.1 Hz), 2.68 (6H, m), 3.97 (4H, m), 7.32 (1H, d, J=8.3 Hz), 7.43 (2H, m), 7.87 (1H, m), 8.01 (2H, m), 8.30 (1H, s), 8.33 (1H, s)

Mass spectrometric value (ESI-MS) 649 (M−1)

Compound 632 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[3-(4-methoxy-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo-[b]thiophen-2-yl]-benzamide

The title compound 632 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.13 (6H, m), 1.86 (4H, m), 2.49 (2H, m), 2.62 (2H, m), 2.70 (2H, m), 2.81 (2H, m), 3.75-4.05 (7H, m), 6.82 (2H, m), 7.42 (2H, m), 7.74 (2H, m), 8.01 (1H, m), 8.06 (1H, s), 8.23 (1H, m)

Mass spectrometric value (ESI-MS) 577 (M−1)

Compound 633 N-[3-(3,4-Dimethyl-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl]-3-(4-hydroxy-piperidin-1-ylmethyl)-benzamide

The title compound 633 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.64 (2H, m), 1.85 (6H, m), 2.25 (8H, m), 2.75 (6H, m), 3.63 (2H, s), 3.70 (1H, m), 7.15 (1H, d, J=7.8 Hz), 7.43 (2H, m), 7.56 (1H, m), 7.61 (1H, s), 7.93 (1H, d, J=7.8 Hz), 7.98 (1H, s), 8.06 (1H, s)

Mass spectrometric value (ESI-MS) 543 (M−1)

Compound 634 3-(4-Hydroxy-piperidin-1-ylmethyl)-N-[3-(4-methyl-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl]-benzamide

The title compound 634 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.64 (2H, m), 1.86 (6H, m), 2.26 (2H, t, J=9.5 Hz), 2.37 (3H, s), 2.71 (2H, m), 2.81 (4H, m), 3.64 (2H, s), 3.72 (1H, m), 7.19 (2H, d, J=7.9 Hz), 7.43 (1H, dd, J=7.8 Hz), 7.57 (1H, d, J=7.8 Hz), 7.66 (2H, d, J=7.9 Hz), 7.94 (2H, m), 8.09 (1H, s)

Mass spectrometric value (ESI-MS) 529 (M−1)

Compound 635 N-[3-(4-Fluoro-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl]-3-(4-hydroxy-piperidin-1-ylmethyl)-benzamide

The title compound 635 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.64 (2H, m), 1.90 (6H, m), 2.23 (2H, m), 2.80 (6H, m), 3.62 (2H, s), 3.73 (1H, m), 7.11 (2H, dd, J=8.6 Hz, J=8.6 Hz), 7.45 (1H, m), 7.58 (1H, m), 7.79 (2H, dd, J=8.6 Hz, J=8.6 Hz), 7.94 (1H, d, J=7.8 Hz), 7.99 (1H, s), 8.12 (1H, s)

Mass spectrometric value (ESI-MS) 533 (M−1)

Compound 636 N-[3-(3-Fluoro-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl]-3-(4-hydroxy-piperidin-1-ylmethyl)-benzamide

The title compound 636 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.69 (2H, m), 1.90 (6H, m), 2.42 (2H, bs), 2.78 (6H, m), 3.75 (3H, m), 7.11 (1H, m), 7.30-7.80 (5H, m), 7.98 (2H, m), 8.14 (1H, s)

Mass spectrometric value (ESI-MS) 533 (M−1)

Compound 637 N-[3-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl]-3-(4-hydroxy-piperidin-1-ylmethyl)-benzamide

The title compound 637 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.63 (2H, m), 1.85 (6H, m), 2.19 (2H, m), 2.74 (6H, m), 3.58 (2H, s), 3.71 (1H, m), 7.44 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.54 (2H, m), 7.94 (4H, m), 8.23 (1H, s)

Mass spectrometric value (ESI-MS) 617 (M−1)

Compound 638 3-(4-Hydroxy-piperidin-1-ylmethyl)-N-[3-(4-methoxy-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl]-benzamide

The title compound 638 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.62 (2H, m), 1.87 (6H, m), 2.19 (2H, m), 2.77 (6H, m), 3.59 (2H, s), 3.70 (1H, m), 3.83 (3H, s), 6.90 (2H, d, J=8.5 Hz), 7.43 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.55 (1H, d, J=7.6 Hz), 7.72 (2H, d, J=8.5 Hz), 7.92 (1H, d, J=7.6 Hz), 7.98 (1H, s), 8.06 (1H, s)

Mass spectrometric value (ESI-MS) 545 (M−1)

Compound 639 N-[3-(3,4-Dimethyl-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl]-3-(4-hydroxymethyl-piperidin-1-ylmethyl)-benzamide

The title compound 639 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.37 (2H, m), 1.49 (1H, m), 1.71 (2H, m), 1.86 (4H, m), 2.04 (2H, m), 2.29 (6H, s), 2.73 (2H, m), 2.86 (2H, m), 2.93 (2H, m), 3.49 (2H, d, J=6.3 Hz), 3.62 (2H, s), 7.16 (1H, d, J=7.8 Hz), 7.45 (2H, m), 7.58 (1H, m), 7.63 (1H, s), 7.94 (1H, d, J=7.8 Hz), 7.99 (1H, s), 8.05 (1H, s)

Mass spectrometric value (ESI-MS) 557 (M−1)

Compound 640 3-(4-Hydroxymethyl-piperidin-1-ylmethyl)-N-[3-(4-methyl-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl]-benzamide

The title compound 640 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.40 (2H, m), 1.50 (1H, m), 1.71 (2H, m), 1.89 (4H, m), 2.06 (2H, m), 2.38 (3H, m), 2.73 (2H, m), 2.86 (2H, m), 2.95 (2H, m), 3.49 (2H, d, J=6.1 Hz), 3.63 (2H, s), 7.21 (2H, d, J=8.0 Hz), 7.45 (1H, dd, J=7.7 Hz, J=14.9 Hz), 7.59 (1H, d, J=7.6 Hz), 7.68 (2H, d, J=8.0 Hz), 7.97 (2H, m), 8.09 (1H, s)

Mass spectrometric value (ESI-MS) 543 (M−1)

Compound 641 N-[3-(4-Fluoro-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl]-3-(4-hydroxymethyl-piperidin-1-ylmethyl)-benzamide

The title compound 641 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.34 (2H, m), 1.50 (1H, m), 1.69 (2H, m), 1.84 (4H, m), 2.01 (2H, m), 2.71 (2H, m), 2.87 (4H, m), 3.49 (2H, d, J=6.4 Hz), 3.58 (2H, s), 7.10 (2H, dd, J=8.5 Hz), 7.43 (1H, m), 7.55 (1H, m), 7.78 (2H, m), 7.91 (1H, m), 7.98 (1H, bs), 8.13 (1H, s)

Mass spectrometric value (ESI-MS) 547 (M−1)

Compound 642 N-[3-(3-Fluoro-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl]-3-(4-hydroxymethyl-piperidin-1-ylmethyl)-benzamide

The title compound 642 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.35 (2H, m), 1.51 (1H, m), 1.70 (2H, m), 1.84 (4H, m), 2.01 (2H, m), 2.70 (2H, m), 2.83 (2H, m), 2.90 (2H, m), 3, 49 (2H, d, J=6.3 Hz), 3.58 (2H, s), 7.10 (1H, ddd, J=8.3 Hz, J=8.3 Hz, J=2.7 Hz), 7.45 (5H, m), 7.90 (1H, d, J=7.4 Hz), 7.98 (1H, s), 8.14 (1H, s)

Mass spectrometric value (ESI-MS) 547 (M−1)

Compound 643 N-[3-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl]-3-(4-hydroxymethyl-piperidin-1-ylmethyl)-benzamide

The title compound 643 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.39 (2H, m), 1.52 (1H, m), 1.72 (2H, m), 1.88 (4H, m), 2.05 (2H, m), 2.66-2.98 (6H, m), 3.50 (2H, d, J=6.1 Hz), 3.61 (2H, s), 7.46 (1H, m), 7.57 (1H, m), 7.86 (1H, m), 7.96 (3H, m), 8.04 (1H, s), 8.21 (1H, s)

Mass spectrometric value (ESI-MS) 631 (M−1)

Compound 644 3-(4-Hydroxymethyl-piperidin-1-ylmethyl)-N-[3-(4-methoxy-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo-[b]thiophen-2-yl]-benzamide

The title compound 644 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.34 (2H, m), 1.49 (1H, m), 1.69 (2H, m), 1.84 (4H, m), 2.00 (2H, m), 2.69 (2H, m), 2.81 (2H, m), 2.88 (2H, m), 3.48 (2H, d, J=6.4 Hz), 3.57 (2H, s), 3.83 (3H, s), 6.90 (2H, d, J=8.8 Hz), 7.43 (1H, m), 7.55 (1H, m), 7.70 (2H, d, J=8.8 Hz), 7.91 (1H, d, J=7.8 Hz), 7.97 (1H, m), 8.07 (1H, s)

Mass spectrometric value (ESI-MS) 559 (M−1)

Compound 645 N-{3-[N′-(3,4-Dimethyl-benzyl)-hydrazinocarbonyl]-4-methyl-thiophen-2-yl}-3-(3-hydroxy-propylsulfanylmethyl)-benzamide

The title compound 645 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.87 (2H, m), 2.26 (9H, m), 2.56 (2H, m), 3.73 (2H, m), 3.82 (2H, s), 4.06 (2H, s), 6.46 (1H, s), 7.13 (1H, bs), 7.18 (1H, bs), 7.50 (1H, m), 7.57 (1H, d, J=7.8 Hz), 7.93 (2H, m), 13.00 (1H, s)

Mass spectrometric value (ESI-MS) 496 (M−1)

Compound 646 3-[(3,4-Dimethyl-benzylidene-)-amino]-2-[3-(1H-[1,2,4]triazol-3-ylsulfanylmethyl)-phenyl]-5,6,7,8-tetrahydro-3H-benzo[4,5]thieno[2,3-d]pyrimidin-4-one

The title compound 646 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.88 (4H, m), 2.31 (3H, s), 2.33 (3H, s), 2.80 (2H, m), 3.05 (2H, m), 4.33 (2H, s), 7.10-7.88 (7H, m), 8.03 (1H, s), 8.76 (1H, s)

Mass spectrometric value (ESI-MS) 525 (M−1)

Compound 647 3-[(4-Methyl-benzylidene-)-amino]-2-[3-(1H-[1,2,4]triazol-3-ylsulfanylmethyl)-phenyl]-5,6,7,8-tetrahydro-3H-benzo[4,5]thieno[2,3-d]pyrimidin-4-one

The title compound 647 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.88 (4H, m), 2.35 (3H, s), 2.80 (2H, m), 3.05 (2H, m), 4.34 (2H, s), 7.17 (2H, d, J=7.8 Hz), 7.26 (1H, m), 7.37 (1H, m), 7.56 (2H, m), 7.76 (1H, s), 8.00 (2H, m), 8.81 (1H, s)

Mass spectrometric value (ESI-MS) 511 (M−1)

Compound 648 3-[(4-Fluoro-benzylidene-)-amino]-2-[3-(1H-[1,2,4]triazol-3-ylsulfanylmethyl)-phenyl]-5,6,7,8-tetrahydro-3H-benzo[4,5]thieno[2,3-d]pyrimidin-4-one

The title compound 648 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.89 (4H, m), 2.81 (2H, m), 3.05 (2H, m), 4.36 (2H, s), 7.08 (2H, dd, J=8.7 Hz), 7.31 (1H, m), 7.40 (1H, d, J=7.8 Hz), 7.56 (1H, d, J=7.8 Hz), 7.69 (2H, m), 7.76 (1H, m), 8.04 (1H, s), 8.92 (1H, s)

Mass spectrometric value (ESI-MS) 515 (M−1)

Compound 649 3-[(3-Fluoro-benzylidene)-amino]-2-[3-(1H-[1,2,4]triazol-3-ylsulfanylmethyl)-phenyl]-5,6,7,8-tetrahydro-3H-benzo[4,5]thieno[2,3-d]pyrimidin-4-one

The title compound 649 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.89 (4H, m), 2.81 (2H, m), 3.05 (2H, m), 4.36 (2H, s), 7.15 (1H, m), 7.36 (5H, m), 7.55 (1H, m), 7.75 (1H, m), 8.03 (1H, s), 9.01 (1H, s)

Mass spectrometric value (ESI-MS) 515 (M−1)

Compound 650 3-[(4-Chloro-3-trifluoromethyl-benzylidene)-amino]-2-[3-(1H-[1,2,4]triazol-3-ylsulfanylmethyl)-phenyl]-5,6,7,8-tetrahydro-3H-benzo[4,5]thieno[2,3-d]pyrimidin-4-one

The title compound 650 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.89 (4H, m), 2.68 (2H, m), 2.81 (2H, m), 4.37 (2H, s), 7.30-8.02 (7H, m), 8.06 (1H, m), 9.17 (1H, s)

Mass spectrometric value (ESI-MS) 599 (M−1)

Compound 651 3-[(4-Methoxy-benzylidene)-amino]-2-[3-(1H-[1,2,4]triazol-3-ylsulfanylmethyl)-phenyl]-5,6,7,8-tetrahydro-3H-benzo[4,5]thieno[2,3-d]pyrimidin-4-one

The title compound 651 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.88 (4H, m), 2.80 (2H, m), 3.05 (2H, m), 3.81 (3H, s), 4.33 (2H, s), 6.87 (2H, d, J=8.8 Hz), 7.28 (1H, m), 7.55 (1H, m), 7.61 (2H, d, J=8.8 Hz), 7.76 (1H, m), 8.00 (1H, s), 8.73 (1H, s), 9.15 (1H, s)

Mass spectrometric value (ESI-MS) 527 (M−1)

Example 9

Compound 652 3-{[Acetyl-(2-diethylamino-ethyl)-amino]-methyl}-N-[3-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl]-benzamide

2-Amino-4,5,6,7-tetrahydrobenzothiophene-3-carboxylic acid ethyl ester (Compound A) (4.0 g) was dissolved in anhydrous methylene chloride (40.0 ml). Subsequently, pyridine (2.8 ml) and 3-(chloromethyl)benzoyl chloride (compound B) (3.0 ml) were added at 0° C., and the mixture was stirred at 0° C. for one hr. After the completion of the reaction, distilled water was added, and the mixture was subjected to separatory extraction with chloroform, and the organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated to give 2-(3-chloromethyl-benzoylamino)-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid ethyl ester as a useful intermediate (7.42 g, yield 100%).

2-(3-Chloromethyl-benzoylamino)-4,5,6,7-tetrahydro-benzo[b]-thiophene-3-carboxylic acid ethyl ester (800 mg) produced by the above reaction was dissolved in anhydrous methylene chloride (5.0 ml). Triethylamine (580 μl) and N,N-diethylethylenediamine (compound B′) (464 mg) were added to the solution at room temperature, and the mixture was stirred at room temperature for 15 hr. After the completion of the reaction, water was added at room temperature, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated to give 2-{3-[(2-diethylamino-ethylamino)-methyl]-benzoylamino}-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid ethyl ester as a crude useful intermediate (902 mg, yield 100%).

2-{3-[(2-Diethylamino-ethylamino)-methyl]-benzoylamino}-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid ethyl ester produced by the above reaction was dissolved in ethanol (5.0 ml). Hydrazine monohydrate (2 ml) was added to the solution, and the mixture was heated under reflux with stirring for 15 hr. After the completion of the reaction, water was added at room temperature, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated to give 3-[(2-diethylamino-ethylamino)-methyl]-N-(3-hydrazinocarbonyl-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl)-benzamide as a hydrazine compound (464 mg, yield 52%).

3-[(2-Diethylamino-ethylamino)-methyl]-N-(3-hydrazinocarbonyl-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl)-benzamide (77 mg) was dissolved in anhydrous toluene (1.0 ml). Acetic acid (50.0 μl) and 3,4-dimethylbenzaldehyde (compound C) (55.0 μl) were added to the solution at room temperature, and the mixture was heated under reflux with stirring for 15 hr. After the completion of the reaction, the reaction product was purified by column chromatography eluted with a chloroform-methanol system to give the title compound 652 (58.4 mg, yield 58%).

¹H-NMR (CDCl₃, 400 MHz): δ 0.98 (6H, m), 1.85 (7H, m), 2.28 (6H, m), 2.45-2.90 (12H, m), 3.76 (2H, m), 7.14 (1H, m), 7.32-8.12 (7H, m)

Mass spectrometric value (ESI-MS) 600 (M−1)

Compound 653 3-{[Acetyl-(2-diethylamino-ethyl)-amino]-methyl}-N-[3-(4-methyl-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo[b]-thiophen-2-yl]-benzamide

The title compound 653 was produced in substantially the same manner as in Example 9.

¹H-NMR (CDCl₃, 400 MHz): δ 0.98 (6H, m), 1.83 (7H, m), 2.38 (3H, s), 2.42-2.90 (12H, m), 3.75 (2H, m), 7.24 (2H, m), 7.40-8.15 (7H, m)

Mass spectrometric value (ESI-MS) 586 (M−1)

Compound 654 3-{[Acetyl-(2-diethylamino-ethyl)-amino]-methyl}-N-[3-(4-fluoro-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo[b]-thiophen-2-yl]-benzamide

The title compound 654 was produced in substantially the same manner as in Example 9.

¹H-NMR (CDCl₃, 400 MHz): δ 0.93 (6H, m), 1.83 (7H, m), 2.48 (4H, m), 2.69 (6H, m), 2.80 (2H, m), 3.75 (2H, m), 7.06 (2H, m), 7.40-7.95 (6H, m), 8.09 (1H, s)

Mass spectrometric value (ESI-MS) 590 (M−1)

Compound 655 3-{[Acetyl-(2-diethylamino-ethyl)-amino]-methyl}-N-[3-(3-fluoro-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo[b]-thiophen-2-yl]-benzamide

The title compound 655 was produced in substantially the same manner as in Example 9.

¹H-NMR (CDCl₃, 400 MHz): δ 0.94 (6H, m), 1.83 (7H, m), 2.62 (12H, m), 3.76 (2H, m), 7.08 (1H, m), 7.29-8.20 (8H, m)

Mass spectrometric value (ESI-MS) 590 (M−1)

Compound 656 3-{[Acetyl-(2-diethylamino-ethyl)-amino]-methyl}-N-[3-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl]-benzamide

The title compound 656 was produced in substantially the same manner as in Example 9.

¹H-NMR (CDCl₃, 400 MHz): δ 0.93 (6H, m), 1.83 (7H, m), 2.62 (12H, m), 3.77 (2H, m), 7.40-8.30 (8H, m)

Mass spectrometric value (ESI-MS) 674 (M−1)

Compound 657 3-{[Acetyl-(2-diethylamino-ethyl)-amino]-methyl}-N-[3-(4-methoxy-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl]-benzamide

The title compound 657 was produced in substantially the same manner as in Example 9.

¹H-NMR (CDCl₃, 400 MHz): δ 0.98 (6H, m), 1.87 (7H, m), 2.63 (12H, m), 3.77 (2H, m), 3.84 (3H, s), 6.89 (2H, m), 7.40-8.10 (7H, m)

Mass spectrometric value (ESI-MS) 602 (M−1)

Compound 658 N-[3-(3,4-Dimethyl-benzylidene-hydrazinocarbonyl)-thiophen-2-yl]-3-(3-hydroxy-propylsulfanylmethyl)-benzamide

The title compound 658 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.80 (2H, m), 2.30 (3H, s), 2.31 (3H, s), 2.53 (2H, t, J=7.4 Hz), 3.62 (2H, m), 3.85 (2H, s), 7.00 (1H, d, J=6.1 Hz), 7.18 (1H, d, J=7.8 Hz), 7.52 (3H, m), 7.64 (2H, m), 7.90 (1H, s), 7.97 (1H, s), 8.28 (1H, s)

Mass spectrometric value (ESI-MS) 480 (M−1)

Compound 659 3-(3-Hydroxy-propylsulfanylmethyl)-N-[3-(4-methyl-benzylidene-hydrazinocarbonyl)-thiophen-2-yl]-benzamide

The title compound 659 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.79 (2H, m), 2.35 (3H, s), 2.53 (2H, t, J=7.3 Hz), 3.62 (2H, t, J=6.2 Hz), 3.82 (2H, s), 6.97 (1H, d, J=5.8 Hz), 7.21 (2H, d, J=7.8 Hz), 7.49 (2H, m), 7.60 (1H, d, J=7.80), 7.69 (2H, d, J=7.8 Hz), 7.87 (1H, m), 7.94 (1H, s), 8.27 (1H, s)

Mass spectrometric value (ESI-MS) 466 (M−1)

Compound 660 N-[3-(4-Fluoro-benzylidene-hydrazinocarbonyl)-thiophen-2-yl]-3-(3-hydroxy-propylsulfanylmethyl)-benzamide

The title compound 660 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.80 (2H, m), 2.53 (2H, t, J=7.4 Hz), 3.62 (2H, t, J=6.4 Hz), 3.82 (2H, s), 6.96 (1H, d, J=5.9 Hz), 7.14 (2H, dd, J=8.7 Hz), 7.48 (2H, m), 7.60 (1H, d, J=7.6 Hz), 7.85 (3H, m), 7.93 (1H, s), 8.29 (1H, s)

Mass spectrometric value (ESI-MS) 470 (M−1)

Compound 661 N-[3-(3-Fluoro-benzylidene-hydrazinocarbonyl)-thiophen-2-yl]-3-(3-hydroxy-propylsulfanylmethyl)-benzamide

The title compound 661 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.80 (2H, m), 2.54 (2H, t, J=7.3 Hz), 3.62 (2H, t, J=9.4 Hz), 3.86 (2H, s), 7.03 (1H, d, J=5.8 Hz), 7.17 (1H, m), 7.42-7.80 (6H, m), 7.87 (1H, m), 7.98 (1H, bs), 8.35 (1H, s)

Mass spectrometric value (ESI-MS) 470 (M−1)

Compound 662 N-[3-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-thiophen-2-yl]-3-(3-hydroxy-propylsulfanylmethyl)-benzamide

The title compound 662 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.80 (1H, m), 2.54 (2H, t, J=7.3 Hz), 3.62 (2H, t, J=6.2 Hz), 3.86 (2H, s), 7.03 (1H, d, J=5.8 Hz), 7.53 (2H, m), 7.66 (2H, m), 7.90 (1H, d, J=7.8 Hz), 7.98 (1H, bs), 8.04 (1H, d, J=8.8 Hz), 8.33 (1H, s), 8.38 (1H, s)

Mass spectrometric value (ESI-MS) 554 (M−1)

Compound 663 3-(3-Hydroxy-propylsulfanylmethyl)-N-[3-(4-methoxy-benzylidene-hydrazinocarbonyl)-thiophen-2-yl]-benzamide

The title compound 663 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.80 (2H, m), 2.54 (2H, t, J=7.3 Hz), 3.62 (2H, t, J=6.2 Hz), 3.85 (6H, m), 6.99 (2H, d, J=8.8 Hz), 7.02 (1H, s, J=5.9 Hz), 7.53 (2H, m), 7.65 (1H, d, J=7.8 Hz), 7.79 (2H, d, J=8.5 Hz), 7.90 (1H, d, J=7.8 Hz), 8.30 (1H, s)

Mass spectrometric value (ESI-MS) 482 (M−1)

Compound 664 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[3-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-thiophen-2-yl]-benzamide

The title compound 664 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.04 (6H, t, J=7.1 Hz), 2.22 (9H, m), 2.62 (8H, m), 3.59 (2H, s), 6.77 (1H, d, J=5.4 Hz), 7.09 (1H, m), 7.44 (5H, m), 7.94 (2H, d, J=7.6 Hz), 8.26 (1H, s)

Mass spectrometric value (ESI-MS) 518 (M−1)

Compound 665 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[3-(4-methyl-benzylidene-hydrazinocarbonyl)-thiophen-2-yl]-benzamide

The title compound 665 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.03 (6H, t, J=7.1 Hz), 2.21 (3H, s), 2.34 (3H, s), 2.59 (8H, m), 3.58 (2H, s), 6.80 (1H, d, J=4.6 Hz), 7.16 (2H, m), 7.42 (2H, m), 7.58 (3H, m), 7.93 (1H, d, J=7.8 Hz), 7.98 (1H, s), 8.28 (1H, s)

Mass spectrometric value (ESI-MS) 504 (M−1)

Compound 666 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[3-(4-fluoro-benzylidene-hydrazinocarbonyl)-thiophen-2-yl]-benzamide

The title compound 666 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.04 (6H, t, J=7.1 Hz), 2.21 (3H, s), 2.62 (8H, m), 3.58 (2H, s), 6.78 (1H, d, J=4.6 Hz), 7.02 (2H, m), 7.42 (2H, m), 7.55 (1H, d, J=7.6 Hz), 7.67 (2H, m), 7.91 (1H, d, J=7.8 Hz), 7.96 (1H, s), 8.36 (1H, s)

Mass spectrometric value (ESI-MS) 508 (M−1)

Compound 667 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[3-(3-fluoro-benzylidene-hydrazinocarbonyl)-thiophen-2-yl]-benzamide

The title compound 667 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.04 (6H, t, J=7.1 Hz), 2.20 (3H, s), 2.60 (8H, m), 3.57 (2H, s), 6.76 (1H, bs), 7.02 (1H, m), 7.41 (6H, m), 7.91 (1H, d, J=7.8 Hz), 7.97 (1H, s), 8.38 (1H, bs)

Mass spectrometric value (ESI-MS) 508 (M−1)

Compound 668 N-[3-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-thiophen-2-yl]-3-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 668 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.02 (6H, t, J=7.1 Hz), 2.20 (3H, s), 2.58 (8H, m), 3.56 (2H, s), 6.74 (1H, bs), 7.41 (2H, m), 7.54 (2H, d, J=7.6 Hz), 7.76 (1H, dd, J=8.3 Hz, J=1.4 Hz), 7.88 (2H, m), 7.96 (1H, s), 8.45 (1H, bs)

Mass spectrometric value (ESI-MS) 592 (M−1)

Compound 669 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[3-(4-methoxy-benzylidene-hydrazinocarbonyl)-thiophen-2-yl]-benzamide

The title compound 669 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.01 (6H, t, J=7.1 Hz), 2.19 (3H, s), 2.56 (8H, m), 3.56 (2H, s), 3.75 (3H, s), 6.75 (1H, m), 6.81 (2H, m), 7.42 (2H, m), 7.87 (3H, m), 7.90 (1H, d, J=7.84), 7.97 (1H, s), 8.32 (1H, s)

Mass spectrometric value (ESI-MS) 520 (M−1)

Compound 670 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[3-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-thiophen-2-yl]-benzamide

The title compound 670 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.11 (6H, m), 2.30 (3H, s), 2.32 (3H, s), 2.52 (4H, m), 3.83 (4H, m), 7.01 (1H, d, J=5.8 Hz), 7.19 (1H, d, J=7.8 Hz), 7.53 (3H, m), 7.67 (2H, m), 7.93 (1H, d, J=7.6 Hz), 8.06 (1H, m), 8.29 (1H, s)

Mass spectrometric value (ESI-MS) 521 (M−1)

Compound 671 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[3-(4-methyl-benzylidene-hydrazinocarbonyl)-thiophen-2-yl]-benzamide

The title compound 671 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.11 (6H, d, J=6.1 Hz), 2.39 (3H, s), 2.52 (4H, m), 3.82 (4H, m), 7.01 (1H, m), 7.26 (2H, d, J=7.6 Hz), 7.53 (2H, m), 7.68 (1H, d, J=7.1 Hz), 7.74 (2H, d, J=7.8 Hz), 7.92 (1H, d, J=7.6 Hz), 8.06 (1H, m), 8.33 (1H, s)

Mass spectrometric value (ESI-MS) 507 (M−1)

Compound 672 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[3-(4-fluoro-benzylidene-hydrazinocarbonyl)-thiophen-2-yl]-benzamide

The title compound 672 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.10 (6H, d, J=6.3 Hz), 2.51 (4H, m), 3.86 (4H, m), 7.02 (1H, d, J=5.9 Hz), 7.18 (2H, dd, J=8.4 Hz, J=8.4 Hz), 7.53 (2H, m), 7.68 (1H, dd, J=7.6 Hz), 7.91 (3H, m), 8.06 (1H, m), 8.35 (1H, s)

Mass spectrometric value (ESI-MS) 511 (M−1)

Compound 673 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[3-(3-fluoro-benzylidene-hydrazinocarbonyl)-thiophen-2-yl]-benzamide

The title compound 673 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.11 (6H, m), 2.52 (4H, m), 3.87 (4H, m), 7.03 (1H, d, J=6.1 Hz), 7.15 (1H, m), 7.40-7.75 (6H, m), 7.90 (1H, m), 8.07 (1H, m), 8.36 (1H, m)

Mass spectrometric value (ESI-MS) 511 (M−1)

Compound 674 3-[(4-Chloro-3-trifluoromethyl-benzylidene)-amino]-2-(3-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-phenyl)-5,6,7,8-tetrahydro-3H-benzo[4,5]thieno[2,3-d]pyrimidin-4-one

The title compound 674 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 0.99 (6H, t, J=7.1 Hz), 1.90 (4H, m), 2.12 (3H, s), 2.50 (8H, m), 2.82 (2H, m), 3.05 (2H, m), 3.52 (2H, s), 7.38 (2H, m), 7.54 (2H, m), 7.62 (1H, bs), 7.78 (1H, m), 7.98 (1H, m), 9.18 (1H, s)

Mass spectrometric value (ESI-MS) 630 (M+1)

Compound 675 2-(3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-phenyl)-3-[(4-methoxy-benzylidene-)-amino]-5,6,7,8-tetrahydro-3H-benzo[4,5]thieno[2,3-d]pyrimidin-4-one

The title compound 675 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.00 (6H, t, J=7.1 Hz), 1.89 (4H, m), 2.11 (3H, s), 2.52 (8H, m), 2.81 (2H, m), 3.06 (2H, m), 3.50 (2H, s), 3.84 (3H, s), 6.89 (2H, d, J=8.8 Hz), 7.35 (2H, m), 7.58 (1H, m), 7.66 (3H, m), 8.77 (1H, s)

Mass spectrometric value (ESI-MS) 558 (M+1)

Compound 676 N-[4-Bromo-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-(2-hydroxy-ethanesulfonylmethyl)-benzamide

The title compound 676 was produced in the same manner as in Example 6.

¹H-NMR (CD₃OD, 400 MHz): δ 8.58 (1H, d, J=8.8 Hz), 8.34 (1H, s), 8.07 (1H, d, J=2.2 Hz), 8.00 (2H, s), 7.23-7.78 (3H, m), 7.57-7.63 (2H, m), 7.27 (2H, d, J=2.0 Hz), 4.39 (1H, d, J=13.2 Hz), 4.20 (1H, d, J=13.2 Hz), 3.96-4.05 (2H, m), 3.00-3.15 (1H, m), 2.80-2.95 (1H, m), 2.39 (3H, s)

Mass spectrometric value (ESI-MS) 556, 558 (M−1)

Compound 677 N-[4-Bromo-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-(2-hydroxy-ethanesulfinylmethyl)-benzamide

The title compound 677 was produced in the same manner as in Example 6.

¹H-NMR (CD₃OD, 400 MHz): δ 8.61 (1H, d, J=9.0 Hz), 8.34 (1H, s), 8.06-8.13 (2H, m), 8.04 (1H, d, J=8.3 Hz), 7.72-7.79 (4H, m), 7.60 (1H, dd, J=7.8 Hz, J=7.8 Hz), 7.28 (2H, d, J=8.1 Hz), 4.83 (2H, s), 4.05 (2H, t, J=5.6 Hz), 3.20 (2H, t, J=5.6 Hz), 2.39 (3H, s)

Mass spectrometric value (ESI-MS) 542, 543 (M−1)

Compound 678 N-[4-Bromo-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-(2-hydroxy-ethanesulfonylmethyl)-benzamide

The title compound 678 was produced in the same manner as in Example 6.

¹H-NMR (CD₃OD, 400 MHz): δ 8.55 (1H, d, J=9.0 Hz), 8.40 (1H, s), 8.32 (1H, s), 8.07 (1H, d, J=2.0 Hz), 8.05 (1H, s, J=8.5 Hz), 7.96-8.05 (2H, m), 7.77 (1H, dd, J=2.0 Hz, J=8.8 Hz), 7.69 (1H, d, J=8.3 Hz), 7.56-7.66 (2H, m), 4.39 (1H, d, J=12.9 Hz), 4.20 (1H, d, J=13.2 Hz), 3.96-4.03 (2H, m), 3.03-3.13 (1H, m), 2.87 (1H, dt, J=4.2 Hz, J=13.4 Hz)

Mass spectrometric value (ESI-MS) 664, 646 (M−1)

Compound 679 N-[4-Bromo-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-(2-hydroxy-ethanesulfinylmethyl)-benzamide

The title compound 679 was produced in the same manner as in Example 6.

¹H-NMR (CDCl₃, 400 MHz): δ 8.70-8.80 (1H, m), 8.20-8.27 (1H, m), 8.05-8.15 (2H, m), 7.97 (2H, s), 7.60-7.70 (3H, m), 7.49-7.60 (2H, m), 4.52 (2H, m), 4.22-4.26 (2H, m), 3.10-3.15 (2H, m)

Mass spectrometric value (ESI-MS) 628, 630 (M−1)

Compound 680 N-[4-Chloro-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-3-(furan-2-ylmethylsulfanylmethyl)-benzamide

The title compound 680 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.64 (1H, d, J=9.0 Hz), 8.36 (1H, s), 7.93-7.97 (2H, m), 7.85-7.90 (1H, m), 7.69 (1H, d, J=10.0 Hz), 7.63 (1H, dd, J=2.4 Hz, J=9.0 Hz), 7.58 (2H, dd, J=7.6 Hz, J=7.6 Hz), 7.50 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.40-7.48 (2H, m), 7.18 (2H, m), 6.29-6.33 (1H, m), 6.21 (1H, d, J=3.2 Hz), 3.81 (2H, s), 3.64 (2H, s)

Mass spectrometric value (ESI-MS) 520, 522 (M−1)

Compound 681 N-[4-Chloro-2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-3-(furan-2-ylmethylsulfanylmethyl)-benzamide

The title compound 681 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.64 (1H, d, J=9.0 Hz), 8.35 (1H, s), 7.85-7.96 (5H, m), 7.62 (1H, dd, J=2.4 Hz, J=9.0 Hz), 7.57 (1H, d, J=7.8 Hz), 7.50 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.40-7.42 (1H, m), 7.18 (2H, dd, J=8.8 Hz, J=8.8 Hz), 7.31 (1H, dd, J=2.0 Hz, J=3.2 Hz), 6.21 (1H, d, J=3.2 Hz), 3.81 (2H, s), 3.64 (2H, s)

Mass spectrometric value (ESI-MS) 520, 522 (M−1)

Compound 682 N-[4-Chloro-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-(furan-2-ylmethylsulfanylmethyl)-benzamide

The title compound 682 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.65 (1H, d, J=9.0 Hz), 8.33 (1H, s), 7.91-7.96 (2H, m), 7.85-7.90 (1H, m), 7.73 (2H, d, J=8.0 Hz), 7.62 (1H, dd, J=2.4 Hz, J=9.0 Hz), 7.58 (1H, d, J=7.6 Hz), 7.50 (1H, dd, J=7.8 Hz, J=7.8 Hz), 7.40-7.42 (1H, m), 7.26 (2H, d, J=8.1 Hz), 6.29-6.33 (1H, m), 6.20-6.23 (1H, m), 3.82 (2H, s), 3.64 (2H, s), 2.38 (3H, s)

Mass spectrometric value (ESI-MS) 516, 518 (M−1)

Compound 683 N-[4-Chloro-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-(furan-2-ylmethylsulfanylmethyl)-benzamide

The title compound 683 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.66 (1H, d, J=8.8 Hz), 8.30 (1H, s), 7.86-7.98 (3H, m), 7.48-7.78 (5H, m), 7.41 (1H, s), 7.15-7.27 (1H, m), 6.29-6.35 (1H, m), 6.20-6.25 (1H, m), 3.82 (2H, s), 3.64 (2H, s), 2.31 (6H, s)

Mass spectrometric value (ESI-MS) 530, 532 (M−1)

Compound 684 N1-[4-Chloro-2-({2-[(E)-1-(3,4-dimethylphenyl)methylidene]hydrazino}carbonyl}phenyl}-3-{[{3-[(3-{[4-chloro-2-({2-[(E)-1-(3,4-dimethylphenyl)methylidene]hydrazino}carbonyl}anilino}carbonyl}benzyl}(methyl)amino)propyl](methyl)amino)methyl)benzamide

The title compound 684 was produced in the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 11.57 (2H, s), 10.57 (2H, s), 8.67 (2H, d, J=9.0 Hz), 8.44 (2H, s), 7.80 (2H, s), 7.71-7.73 (2H, m), 7.64 (2H, s), 7.56 (2H, s), 7.38 (4H, dd, J=7.8 Hz, J=7.8 Hz), 7.20-7.35 (4H, m), 7.10 (2H, d, J=7.8 Hz), 3.53 (4H, s), 2.46 (4H, s), 2.23 (6H, s), 2.18 (6H, s), 2.14 (6H, s), 1.80 (2H, s), 1.61 (4H, s)

Mass spectrometric value (ESI-MS) 935 (M−1)

Compound 685 N1-[4-Chloro-2-({2-[(E)-1-(3-fluorophenyl)methylidene]hydrazino}carbonyl}phenyl}-3-{[{3-[(3-{[4-chloro-2-({2-[(E)-1-(3-fluorophenyl)methylidene]hydrazino}carbonyl}-anilino}carbonyl}benzyl}(methyl)amino)propyl)(methyl)amino]methyl]-benzamide

The title compound 685 was produced in the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 8.59 (2H, d, J=9.0 Hz), 8.40 (2H, s), 7.88-7.90 (4H, m), 7.85 (2H, s), 7.79 (2H, d, J=7.1 Hz), 7.63 (2H, d, J=10.5 Hz), 7.52-7.58 (4H, m), 7.35-7.45 (6H, m), 7.12-7.20 (2H, m), 3.62 (4H, s), 2.53 (4H, m), 2.23 (6H, s), 1.78-1.85 (2H, m)

Mass spectrometric value (ESI-MS) 915 (M−1)

Compound 686 N-[4-Chloro-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-(furan-2-ylmethanesulfonylmethyl)-benzamide

The title compound 686 was produced in the same manner as in Example 6.

¹H-NMR (CDCl₃, 400 MHz): δ 8.64 (1H, d, J=9.0 Hz), 8.30 (1H, s), 8.01 (2H, s), 7.88-7.94 (2H, m), 7.52-7.68 (5H, m), 7.20 (1H, d, J=7.8 Hz), 6.50 (1H, d, J=3.2 Hz), 6.42-6.45 (1H, m), 4.25-4.37 (2H, m), 4.11 (1H, d, J=4.7 Hz), 4.08 (1H, d, J=4.7 Hz), 2.32 (3H, s), 2.31 (3H, s)

Mass spectrometric value (ESI-MS) 562, 564 (M−1)

Compound 687 N-[4-Chloro-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-(furan-2-ylmethanesulfinylmethyl)-benzamide

The title compound 687 was produced in the same manner as in Example 6.

¹H-NMR (CDCl₃, 400 MHz): δ 6.37 (1H, s), 8.72 (1H, d, J=8.0 Hz), 8.00-8.22 (3H, m), 7.40-7.80 (7H, m), 6.54 (1H, d, J=3.4 Hz), 6.40-6.45 (1H, m), 4.29 (2H, s), 4.20 (2H, s), 2.29 (6H, s)

Mass spectrometric value (ESI-MS) 546, 548 (M−1)

Compound 688 N-[4-Chloro-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-(furan-2-ylmethanesulfonylmethyl)-benzamide

The title compound 688 was produced in the same manner as in Example 6.

¹H-NMR (CDCl₃, 400 MHz): δ 8.60 (1H, d, J=9.0 Hz), 8.39 (1H, s), 8.32 (1H, s), 7.89-8.07 (4H, m), 7.55-7.73 (5H, m), 6.49 (1H, m), 6.41-6.46 (1H, m), 4.31 (2H, dd, J=13.4 Hz, J=15.8 Hz), 4.09 (2H, dd, J=10.0 Hz, J=14.2 Hz)

Mass spectrometric value (ESI-MS) 636, 638 (M−1)

Compound 689 N-[4-Chloro-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-(furan-2-ylmethanesulfinylmethyl)-benzamide

The title compound 689 was produced in the same manner as in Example 6.

¹H-NMR (CDCl₃, 400 MHz): δ 8.60 (1H, d, J=9.3 Hz), 8.39 (1H, s), 8.32 (1H, s), 7.98-8.09 (3H, m), 7.94 (1H, d, J=2.2 Hz), 7.69 (2H, d, J=8.0 Hz), 7.56-7.67 (3H, m), 6.55 (1H, d, J=3.2 Hz), 6.40-6.47 (1H, m), 4.54 (2H, s), 4.51 (2H, s)

Mass spectrometric value (ESI-MS) 620 (M−1)

Compound 690 N1-[4-Chloro-2-({2-[(E)-1-(4-chloro-3-trifluoromethyl-phenyl)methylidene]hydrazino}carbonyl)phenyl)-3-{[{6-[(3-{[4-chloro-2-({2-[(E)-1-(4-chloro-3-trifluoromethyl-phenyl)methylidene]hydrazino}-carbonyl}anilino}carbonyl}benzyl}(methyl)amino)hexyl)(methyl)amino]-methyl]benzamide

The title compound 690 was produced in the same manner as in Example 8.

Mass spectrometric value (ESI-MS) 1125, 1127 (M−1)

Compound 691 2-{3-[4-Chloro-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenylcarbamoyl]-benzylsulfanyl}-ethanesulfonic acid

The title compound 691 was produced in the same manner as in Example 11.

¹H-NMR (CD₃OD, 400 MHz): δ 8.53 (1H, d, J=9.0 Hz), 8.34 (1H, s), 7.40-8.00 (10H, m), 4.84 (2H, s), 2.90-3.10 (2H, m), 2.70-2.86 (2H, m)

Mass spectrometric value (ESI-MS) 548 (M−1)

Compound 692 2-{3-[4-Chloro-2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenylcarbamoyl]-benzylsulfanyl}-ethanesulfonic acid

The title compound 692 was produced in the same manner as in Example 11.

¹H-NMR (CD₃OD, 400 MHz): δ 8.56 (1H, d, J=8.8 Hz), 7.20-8.35 (11H, m), 3.84-3.90 (2H, m), 2.92-3.04 (2H, m), 2.70-2.88 (2H, m), 2.30-2.40 (3H, m)

Mass spectrometric value (ESI-MS) 544 (M−1)

Compound 693 2-{3-[4-Chloro-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenylcarbamoyl]-benzylsulfanyl}-ethanesulfonic acid

The title compound 693 was produced in the same manner as in Example 11.

¹H-NMR (CD₃OD, 400 MHz): δ 8.55 (1H, d, J=8.8 Hz), 8.32 (1H, s), 7.10-8.00 (10H, m), 3.88 (2H, s), 2.90-3.10 (2H, m), 2.68-2.86 (2H, m), 2.38 (3H, s)

Mass spectrometric value (ESI-MS) 544 (M−1)

Compound 694 2-{3-[4-Chloro-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenylcarbamoyl]-benzylsulfanyl}-ethanesulfonic acid

The title compound 694 was produced in the same manner as in Example 11.

¹H-NMR (CD₃OD, 400 MHz): δ 8.56 (1H, d, J=9.0 Hz), 8.29 (1H, s), 7.46-8.00 (8H, m), 7.18-7.25 (1H, m), 3.87 (2H, s), 2.94-3.10 (2H, m), 2.75-2.86 (2H, m), 2.25-2.35 (6H, m)

Mass spectrometric value (ESI-MS) 582 (M+23)

Compound 695 6-Bromo-3-[(4-fluoro-benzylidene-)-amino]-2-[3-(2-hydroxy-ethylsulfanylmethyl)-phenyl]-3H-quinazolin-4-one

The title compound 695 was produced in the same manner as in Example 10.

¹H-NMR (CDCl₃, 400 MHz): δ 8.98-9.00 (1H, m), 8.46 (1H, s), 7.85 (1H, dd, J=2.2 Hz, J=8.5 Hz), 7.65-7.72 (3H, m), 7.58 (1H, dd, J=1.7 Hz, J=7.3 Hz), 7.35-7.43 (2H, m), 7.07-7.13 (3H, m), 3.73 (2H, s), 3.56-3.64 (2H, m), 2.52-2.58 (2H, m)

Mass spectrometric value (ESI-MS) 534, 536, 537 (M+23)

Compound 696 6-Bromo-2-[3-(2-hydroxy-ethylsulfanylmethyl)-phenyl]-3-[(4-methyl-benzylidene-)-amino]-3H-quinazolin-4-one

The title compound 696 was produced in the same manner as in Example 10.

¹H-NMR (CDCl₃, 400 MHz): δ 8.85 (1H, s), 8.41 (1H, d, J=2.2 Hz), 7.91 (1H, d, J=8.0 Hz), 7.79 (1H, dd, J=2.4 Hz, J=8.8 Hz), 7.59-7.64 (2H, m), 7.52-7.56 (3H, m), 7.28-7.36 (2H, m), 7.14-7.20 (1H, m), 3.67 (2H, s), 3.49 (2H, t, J=6.0 Hz), 2.46 (2H, t, J=6.0 Hz), 2.36 (1H, s), 2.33 (3H, s)

Mass spectrometric value (ESI-MS) 530, 532, 533 (M+23)

Compound 697 6-Bromo-3-[(3,4-dimethyl-benzylidene-)-amino]-2-[3-(2-hydroxy-ethylsulfanylmethyl)-phenyl]-3H-quinazolin-4-one

The title compound 697 was produced in the same manner as in Example 10.

¹H-NMR (CDCl₃, 400 MHz): δ 8.78 (1H, s), 8.41 (2H, d, J=2.2 Hz), 7.79 (1H, dd, J=2.4 Hz, J=8.8 Hz), 7.64 (1H, s), 7.60 (1H, d, J=8.8 Hz), 7.53-7.57 (1H, m), 7.42 (1H, s), 7.28-7.38 (3H, m), 7.11 (1H, d, J=7.8 Hz), 3.67 (2H, s), 3.49 (2H, t, J=6.0 Hz), 2.46 (2H, t, J=6.0 Hz), 2.24 (3H, s), 2.22-2.27 (1H, m), 2.20 (3H, s)

Mass spectrometric value (ESI-MS) 546, 547 (M+23)

Compound 698 6-Bromo-3-[(4-chloro-3-trifluoromethyl-benzylidene-)-amino]-2-[3-(2-hydroxy-ethylsulfanylmethyl)-phenyl]-3H-quinazolin-4-one

The title compound 698 was produced in the same manner as in Example 10.

¹H-NMR (CDCl₃, 400 MHz): δ 9.27 (1H, s), 8.46 (1H, d, J=2.2 Hz), 7.94 (1H, s), 7.86 (1H, dd, J=2.2 Hz, J=8.5 Hz), 7.75 (1H, d, J=8.3 Hz), 7.65-7.68 (2H, m), 7.54 (2H, d, J=7.8 Hz), 7.32-7.45 (2H, m), 3.75 (2H, s), 3.61 (2H, dt, J=5.9 Hz, J=5.9 Hz), 2.57 (2H, t, J=6.0 Hz), 2.03 (1H, t, J=6.1 Hz)

Mass spectrometric value (ESI-MS) 620 (M+23)

Compound 699 N-[4-Chloro-2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-(furan-2-ylmethylsulfanylmethyl)-benzamide

The title compound 699 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.65 (1H, d, J=9.0 Hz), 8.34 (1H, s), 7.91-7.96 (2H, m), 7.85-7.90 (1H, m), 7.69 (1H, s), 7.61 (2H, dd, J=2.4 Hz, J=9.0 Hz), 7.57 (1H, d, J=7.8 Hz), 7.49 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.41 (1H, dd, J=0.8 Hz, J=2.0 Hz), 7.24-7.34 (2H, m), 6.30 (1H, dd, J=2.0 Hz, J=3.2 Hz), 6.21 (1H, d, J=3.2 Hz), 3.81 (2H, s), 3.63 (2H, s), 2.38 (3H, s)

Mass spectrometric value (ESI-MS) 516, 518 (M−1)

Compound 700 N-[4-Chloro-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-(furan-2-ylmethylsulfanylmethyl)-benzamide

The title compound 700 was produced in the same manner as in Example 5.

¹H-NMR (CD₃OD, 400 MHz): δ 8.62 (1H, d, J=9.0 Hz), 8.39 (1H, s), 8.31 (1H, s), 8.04 (1H, d, J=6.8 Hz), 7.92-7.96 (2H, m), 7.87 (1H, d, J=7.8 Hz), 7.69 (1H, d, J=8.6 Hz), 7.64 (1H, dd, J=2.4 Hz, J=9.0 Hz), 7.57 (1H, d, 7.6 Hz), 7.50 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.40 (1H, dd, J=0.8 Hz, J=2.0 Hz), 6.28-6.33 (1H, m), 6.21 (1H, d, J=7.3 Hz), 3.81 (2H, s), 3.64 (2H, s)

Mass spectrometric value (ESI-MS) 604, 606 (M−1)

Compound 701 N1-[4-Chloro-2-({2-[(E)-1-(4-fluorophenyl)methylidene]-hydrazino}carbonyl}phenyl}-3-{[{3-[(3-{[4-chloro-2-([2-[(E)-1-(4-fluorophenyl)methylidene]hydrazino}carbonyl}anilino}carbonyl}benzyl}-(methyl)amino)propyl)(methyl)amino]methyl]benzamide

The title compound 701 was produced in the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 8.59 (2H, d, J=8.8 Hz), 8.41 (2H, s), 7.82-7.90 (8H, m), 7.79 (2H, d, J=7.1 Hz), 7.53 (2H, dd, J=2.4 Hz, J=9.0 Hz), 7.35-7.45 (4H, m), 7.14 (4H, dd, J=8.8 Hz, J=8.8 Hz), 3.59 (4H, s), 2.49 (4H, t, J=6.8 Hz), 2.20 (6H, s), 1.75-1.85 (2H, m)

Mass spectrometric value (ESI-MS) 915, 917 (M−1)

Compound 702 N1-[4-Chloro-2-({2-[(E)-1-(4-methylphenyl)methylidene]-hydrazino}carbonyl}phenyl}-3-{[{3-[(3-{[4-chloro-2-({2-[(E)-1-(4-methylphenyl)methylidene]hydrazino}carbonyl}anilino}carbonyl}benzyl}(methyl)amino)propyl)(methyl)amino]methyl]benzamide

The title compound 702 was produced in the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 8.66 (2H, d, J=9.0 Hz), 8.46 (2H, s), 7.72-7.82 (4H, m), 7.58-7.68 (6H, m), 7.25-7.40 (4H, m), 7.12-7.16 (6H, m), 3.53 (4H, bs), 2.46 (4H, bs), 2.15 (6H, bs), 1.81 (2H, bs)

Mass spectrometric value (ESI-MS) 907, 909 (M−1)

Example 10

Compound 703 2-(3-{6-Chloro-3-[(4-chloro-3-trifluoromethyl-benzylidene)-amino]-4-oxo-3,4-dihydro-quinazolin-2-yl}-benzylsulfanyl)-ethanesulfonic acid

Methyl 2-amino-5-chlorobenzoate (compound A) (4.0 g) was dissolved in anhydrous methylene chloride (80.0 ml). Subsequently, pyridine (2.8 ml) and 3-(chloromethyl)benzoyl chloride (compound B) (5.0 g) were added to the solution at room temperature, and the mixture was stirred at that temperature for 2 hr. After the completion of the reaction, distilled water was added thereto, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with a saturated aqueous sodium chloride solution and saturated brine, was dried over sodium sulfate, and was then concentrated to give methyl 5-chloro-2-[3-(chloromethyl)benzoyl]aminobenzoate as a useful intermediate (3.32 g, yield 100%).

Subsequently, methyl 5-chloro-2-[3-(chloromethyl)benzoyl]-aminobenzoate (1.8 g) was dissolved in anhydrous methylene chloride. Triethylamine (1.5 ml) and 2-mercaptoethanesulfonic acid sodium salt (compound B′) (1.3 g) were added to the solution at room temperature, and the mixture was stirred at 40° C. for 4 days. After the completion of the reaction, distilled water was added thereto at room temperature, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with a saturated aqueous sodium chloride solution, was dried over sodium sulfate, and was then concentrated. The residue was purified by column chromatography on silica gel to give 5-chloro-2-[3-(2-sulfo-ethylsulfanylmethyl)-benzoylamino]-benzoic acid methyl ester as a useful intermediate (1.08 g, yield 46.1%).

5-Chloro-2-[3-(2-sulfo-ethylsulfanylmethyl)-benzoylamino]-benzoic acid methyl ester (1.08 g) produced by the above reaction was dissolved in ethanol (11.0 ml). Hydrazine monohydrate (1.0 ml) was added to the solution at room temperature, and the mixture was heated under reflux with stirring for 3 days. After the completion of the reaction, the reaction solution was allowed to cool at room temperature. The reaction solution as such was then concentrated, and the residue was purified by column chromatography on silica gel to give 2-[3-(3-amino-6-chloro-4-oxo-3,4-dihydroquinazolin-2-yl)-benzylsulfanyl]-ethanesulfonic acid as a quinazolone compound (542 mg, yield 52.1%).

2-[3-(3-Amino-6-chloro-4-oxo-3,4-dihydroquinazolin-2-yl)-benzylsulfanyl]-ethanesulfonic acid (50.0 mg) was dissolved in anhydrous toluene (1.0 ml). Subsequently, 4-chloro-3-trifluoromethylbenzaldehyde (compound C) (50.0 μl) was added to the solution at room temperature, and the mixture was heated under reflux with stirring for 12 hr. After the completion of the reaction, the reaction solution was allowed to cool at room temperature, distilled water was added thereto, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with a saturated aqueous sodium chloride solution and saturated brine, was dried over sodium sulfate, and was then concentrated. The residue was purified by column chromatography on silica gel, followed by drying through a vacuum pump to give the title compound 703 (32.0 mg, yield 44.0%).

¹H-NMR (CDCl₃, 400 MHz): δ 9.16 (1H, s), 8.15-8.25 (1H, m), 7.38-7.90 (9H, m), 3.84 (2H, s), 2.97-3.05 (2H, m), 2.80-2.87 (2H, m)

Mass spectrometric value (ESI-MS) 614, 616 (M−1)

Compound 704 N1-[4-Chloro-2-({2-[(E)-1-(3-fluorophenyl)methylidene]hydrazino}carbonyl}phenyl}-3-{[{6-[(3-{[4-chloro-2-({2-[(E)-1-(3-fluorophenyl)methylidene]hydrazino}carbonyl}-anilino}carbonyl}benzyl}(methyl)amino)hexyl)(methyl)amino]methyl]-benzamide

The title compound 704 was produced in the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 8.60 (2H, d, J=9.0 Hz), 8.35 (2H, s), 7.88-7.95 (4H, m), 7.30-7.80 (14H, m), 7.10-7.20 (2H, m), 3.69 (4H, s), 2.47 (4H, t, J=7.3 Hz), 2.27 (6H, s), 1.50-1.60 (4H, m), 1.25-1.37 (4H, m)

Mass spectrometric value (ESI-MS) 957 (M−1)

Compound 705 N1-[4-Chloro-2-({2-[(E)-1-(3-methylphenyl)methylidene]hydrazino}carbonyl}phenyl}-3-{[{6-[(3-{[4-chloro-2-({2-[(E)-1-(3-methylphenyl)methylidene]hydrazino}carbonyl}-anilino}carbonyl}benzyl}(methyl)amino)hexyl)(methyl)amino]methyl]-benzamide

The title compound 705 was produced in the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 8.61 (2H, d, J=8.8 Hz), 8.35 (2H, s), 7.85-7.93 (4H, s), 7.63 (2H, s), 7.45-7.57 (10H, m), 7.14-7.30 (4H, m), 3.58 (4H, s), 2.35-2.45 (4H, m), 2.34 (6H, s), 2.18 (6H, s), 1.53 (4H, bs), 1.32 (4H, bs)

Mass spectrometric value (ESI-MS) 949 (M−1)

Compound 706 N1-[4-Chloro-2-({2-[(E)-1-(4-methylphenyl)methylidene]hydrazino}carbonyl}phenyl}-3-{[{6-[(3-{[4-chloro-2-({2-[(E)-1-(4-methylphenyl)methylidene]hydrazino}carbonyl}-anilino}carbonyl}benzyl}(methyl)amino)hexyl)(methyl)amino]methyl]-benzamide

The title compound 706 was produced in the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 8.60 (2H, d, J=8.8 Hz), 8.34 (2H, s), 7.83-7.98 (8H, m), 7.66 (2H, d, J=7.8 Hz), 7.48-7.60 (4H, m), 7.21 (6H, d, J=7.8 Hz), 3.78 (4H, s), 2.55-2.60 (4H, m), 2.30-2.35 (12H, m), 1.59 (4H, bs), 1.35 (4H, bs)

Mass spectrometric value (ESI-MS) 949 (M−1)

Compound 707 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-3-yl]-benzamide

The title compound 707 was produced in the same manner as in Example 8.

Mass spectrometric value (ESI-MS) 609, 611, 612 (M−1)

Compound 708 2-{3-[4-Chloro-2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenylcarbamoyl]-benzylsulfanyl}-ethanesulfonic acid

The title compound 708 was produced in the same manner as in Example 11.

¹H-NMR (CD₃OD, 400 MHz): δ 8.54 (1H, d, J=8.8 Hz), 8.34 (1H, s), 7.98 (1H, s), 7.35-7.92 (7H, m), 7.14-7.22 (2H, m), 3.88 (2H, s), 2.95-3.06 (2H, m), 2.70-2.86 (2H, m)

Mass spectrometric value (ESI-MS) 548 (M−1)

Example 11

Compound 709 2-{3-[4-Chloro-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenylcarbamoyl]-benzylsulfanyl}-ethanesulfonic acid

Methyl 2-amino-5-chlorobenzoate (compound A) (4.0 g) was dissolved in anhydrous methylene chloride (80.0 ml). Subsequently, pyridine (2.8 ml) and 3-(chloromethyl)benzoyl chloride (compound B) (5.0 g) were added to the solution at room temperature, and the mixture was stirred at that temperature for 2 hr. After the completion of the reaction, distilled water was added thereto, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with a saturated aqueous sodium chloride solution and saturated brine, was dried over sodium sulfate, and was then concentrated to give methyl 5-chloro-2-[3-(chloromethyl)benzoyl]aminobenzoate (3.32 g, yield 100%) as a useful intermediate.

Subsequently, methyl 5-chloro-2-[3-(chloromethyl)benzoyl]aminobenzoate (1.8 g) was dissolved in anhydrous methylene chloride. Triethylamine (1.5 ml) and 2-mercaptoethanesulfonic acid sodium salt (compound B′) (1.3 g) were added to the solution at room temperature, and the mixture was stirred at 40° C. for 4 days. After the completion of the reaction, distilled water was added thereto at room temperature, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with a saturated aqueous sodium chloride solution, was dried over sodium sulfate, and was then concentrated. The residue was purified by column chromatography on silica gel to give 5-chloro-2-[3-(2-sulfo-ethylsulfanylmethyl)-benzoylamino]-benzoic acid methyl ester (1.08 go yield 46.1%) as a useful intermediate.

5-Chloro-2-[3-(2-sulfo-ethylsulfanylmethyl)-benzoylamino]-benzoic acid methyl ester (1.27 g) produced by the above reaction was dissolved in ethanol (15.0 ml). Hydrazine monohydrate (2.0 ml) was added to the solution at room temperature, and the mixture was stirred at 40° C. for 12 hr. After the completion of the reaction, the reaction solution was allowed to cool at room temperature. The reaction solution as such was then concentrated, and the residue was purified by column chromatography on silica gel to give 2-[3-(4-chloro-2-hydrazinocarbonyl-phenylcarbamoyl)-benzylsulfanyl]-ethanesulfonic acid as a hydrazine compound (820 mg, yield 67.2%).

2-[3-(4-Chloro-2-hydrazinocarbonyl-phenylcarbamoyl)-benzylsulfanyl]-ethanesulfonic acid (50.0 mg) was dissolved in anhydrous toluene (1.0 ml). Subsequently, 4-chloro-3-trifluoromethylbenzaldehyde (compound C) (50.0 μl) was added to the solution at room temperature, and the mixture was heated under reflux with stirring for 12 hr. After the completion of the reaction, the reaction solution was allowed to cool at room temperature, distilled water was added thereto, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with a saturated aqueous sodium chloride solution and saturated brine, was dried over sodium sulfate, and was then concentrated. The residue was purified by column chromatography on silica gel and was dried through a vacuum pump to give the title compound 709 (47.2 mg, yield 56.0%).

¹H-NMR (CD₃OD, 400 MHz): δ 8.52 (1H, d, J=9.0 Hz), 7.38-8.40 (10H, m), 3.89 (2H, s), 2.94-3.06 (2H, m), 2.70-2.88 (2H, m)

Mass spectrometric value (ESI-MS) 632 (M−1)

Compound 710 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[4-methyl-2-(4-methyl-benzylidene-hydrazinocarbonyl)-thiophen-3-yl]-benzamide

The title compound 710 was produced in the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 8.18 (1H, bs), 7.88-8.03 (3H, m), 7.64-7.70 (2H, m), 7.59 (1H, d, J=7.8 Hz), 7.46-7.55 (1H, m), 7.25 (2H, bs), 3.64 (2H, s), 2.72 (2H, bs), 2.53-2.65 (6H, m), 2.37 (3H, s), 2.28 (3H, s), 2.24 (3H, s), 1.04 (6H, t, J=7.3 Hz)

Mass spectrometric value (ESI-MS) 520 (M+1)

Compound 711 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-3-yl]-benzamide

The title compound 711 was produced in the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 7.88-8.18 (3H, m), 7.37-7.64 (5H, m), 7.19 (1H, s), 3.63 (2H, s), 2.67-2.75 (2H, m), 2.53-2.65 (6H, m), 2.20-2.35 (12H, m), 0.98-1.10 (6H, m)

Mass spectrometric value (ESI-MS) 532 (M−1), 534 (M+1)

Compound 712 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[2-(4-methoxy-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-3-yl]-benzamide

The title compound 712 was produced in the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 7.90-8.03 (3H, m), 7.72 (2H, d, J=8.1 Hz), 7.59 (1H, d, J=7.3 Hz), 7.38-7.56 (2H, m), 6.97 (2H, bs), 3.84 (2H, s), 3.64 (2H, s), 2.67-2.75 (2H, m), 2.53-2.65 (6H, m), 2.27 (3H, s), 2.24 (3H, s), 1.00-1.10 (6H, m)

Mass spectrometric value (ESI-MS) 534 (M−1), 536 (M+1)

Compound 713 N-[4-Bromo-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-4-[(2-morpholin-4-yl-ethylamino)-methyl]-benzamide

The title compound 713 was produced in the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 8.43 (2H, bs), 7.99 (2H, d, J=7.8 Hz), 7.68 (1H, s), 7.36-7.60 (6H, m), 7.13 (1H, ddd, J=8.3 Hz, J=8.3 Hz, J=2.0 Hz), 3.89 (2H, s), 3.68-3.73 (4H, m), 2.72 (2H, t, J=5.9 Hz), 2.53 (2H, t, J=6.0 Hz), 2.43 (4H, t, J=4.4 Hz)

Mass spectrometric value (ESI-MS) 582 (M−1)

Compound 714 N-[4-Bromo-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-[(2-morpholin-4-yl-ethylamino)-methyl]-benzamide

The title compound 714 was produced in the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 8.51 (1H, s), 8.31 (1H, d, J=8.3 Hz), 8.06 (1H, s), 7.99 (3H, d, J=7.6 Hz), 7.65 (1H, s), 7.58 (1H, d, J=8.3 Hz), 7.47 (3H, d, J=7.7 Hz), 3.89 (2H, s), 3.71 (4H, t, J=4.5 Hz), 2.71 (2H, t, J=6.0 Hz), 2.53 (2H, t, J=6.0 Hz), 2.43 (4H, bs)

Mass spectrometric value (ESI-MS) 664, 666 (M−1)

Compound 715 N-[4-Bromo-2-(4-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-4-[(2-morpholin-4-yl-ethylamino)-methyl]-benzamide

The title compound 715 was produced in the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 8.43 (1H, d, J=8.8 Hz), 8.38 (1H, s), 7.98 (2H, d, J=8.1 Hz), 7.68-7.77 (3H, m), 7.48 (1H, d, J=8.8 Hz), 7.41 (2H, d, J=8.8 Hz), 6.90 (2H, d, J=8.8 Hz), 3.86 (2H, s), 3.81 (3H, s), 3.68-3.72 (4H, m), 2.69 (2H, t, J=6.0 Hz), 2.51 (2H, t, J=6.0 Hz), 2.38-2.45 (4H, m)

Mass spectrometric value (ESI-MS) 592 (M−1)

Compound 716 N-[4-Bromo-2-(3-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-4-[(2-morpholin-4-yl-ethylamino)-methyl]-benzamide

The title compound 716 was produced in the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 8.40-8.46 (2H, m), 7.98 (2H, d, J=7.8 Hz), 7.71 (1H, s), 7.49 (1H, d, J=8.5 Hz), 7.42 (2H, d, J=8.0 Hz), 7.35 (1H, s), 7.30 (2H, d, J=5.6 Hz), 3.86 (2H, s), 3.84 (3H, s), 3.70 (4H, t, J=4.6 Hz), 2.69 (2H, t, J=4.6 Hz), 2.51 (2H, t, J=5.8 Hz), 2.40-2.47 (4H, m)

Mass spectrometric value (ESI-MS) 596 (M+1)

Compound 717 N-[4-Bromo-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-[4-(4-fluoro-phenyl)-piperazin-1-ylmethyl]-benzamide

The title compound 717 was produced in the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 8.57 (1H, d, J=9.0 Hz), 8.28 (1H, s), 8.00 (2H, d, J=7.6 Hz), 7.55-7.73 (3H, m), 7.48 (3H, d, J=8.1 Hz), 7.18 (1H, d, J=7.8 Hz), 6.93-6.98 (2H, m), 6.85-6.90 (2H, m), 3.63 (2H, s), 3.13 (4H, t, J=4.6 Hz), 2.62 (4H, bs), 2.30 (3H, s), 2.29 (3H, s)

Mass spectrometric value (ESI-MS) 642 (M−1)

Compound 718 4-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[4-bromo-2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 718 was produced in the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 8.53 (1H, d, J=8.6 Hz), 8.35 (1H, s), 8.02 (2H, d, J=7.3 Hz), 7.70 (2H, s), 7.53-7.60 (2H, m), 7.45 (2H, d, J=8.1 Hz), 7.32 (1H, dd, J=7.4 Hz, J=7.4 Hz), 3.60-3.99 (4H, m), 2.42-2.66 (4H, m), 2.39 (3H, s), 1.12 (6H, d, J=6.1 Hz)

Mass spectrometric value (ESI-MS) 581 (M+1)

Compound 719 4-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[4-bromo-2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 719 was produced in the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 8.53 (1H, bs), 8.37 (1H, bs), 8.00 (2H, bs), 7.81 (2H, bs), 7.70 (1H, bs), 7.40-7.60 (3H, m), 7.05-7.15 (2H, m), 3.83-3.98 (2H, m), 3.65-3.78 (2H, m), 2.45-2.60 (4H, m), 1.20-1.30 (3H, m), 1.06-1.16 (3H, m)

Mass spectrometric value (ESI-MS) 587 (M+1)

Compound 720 4-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[4-bromo-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 720 was produced in the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 8.45-8.54 (1H, m), 8.39 (1H, s), 8.00 (2H, d, J=8.3 Hz), 7.36-7.74 (7H, m), 7.10-7.20 (1H, m), 3.80-4.02 (4H, m), 2.47-2.60 (4H, m), 1.12 (6H, d, J=6.4 Hz)

Mass spectrometric value (ESI-MS) 585 (M+1)

Compound 721 4-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[4-bromo-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 721 was produced in the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 8.46 (2H, bs), 7.95-8.08 (3H, m), 7.45-7.75 (4H, m), 7.13-7.20 (2H, m), 3.60-4.03 (4H, m), 2.47-2.68 (4H, m), 1.12 (6H, d, J=6.1 Hz)

Mass spectrometric value (ESI-MS) 667, 669 (M−1)

Compound 722 4-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[4-bromo-2-(4-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 722 was produced in the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 8.37-8.47 (2H, m), 7.98 (2H, d, J=7.8 Hz), 7.70-7.74 (3H, m), 7.38-7.53 (3H, m), 6.90 (2H, d, J=8.8 Hz), 3.77-3.95 (4H, m), 3.81 (3H, s), 2.42-2.64 (4H, m), 1.08-1.14 (6H, m)

Mass spectrometric value (ESI-MS) 597 (M+1)

Compound 723 4-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[4-bromo-2-(3-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 723 was produced in the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 8.57 (1H, d, J=8.5 Hz), 8.34 (1H, s), 8.00 (2H, d, J=7.1 Hz), 7.72 (1H, s), 7.55-7.62 (1H, m), 7.46 (2H, d, J=8.0 Hz), 7.30-7.40 (3H, m), 6.95-7.02 (1H, m), 3.80-4.00 (4H, m), 3.86 (3H, s), 2.40-2.65 (4H, m), 1.09-1.15 (6H, m)

Mass spectrometric value (ESI-MS) 597 (M−1)

Compound 724 N-[4-Bromo-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-({[2-hydroxy-2-(4-hydroxy-phenyl)-ethyl]-methyl-amino}-methyl)-benzamide

The title compound 724 was produced in the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 8.56-8.66 (1H, m), 7.96 (2H, dd, J=2.2 Hz, J=8.3 Hz), 7.87 (1H, d, J=2.4 Hz), 7.65-7.78 (3H, m), 7.46-7.56 (3H, m), 7.13-7.22 (3H, m), 6.72-6.78 (2H, m), 4.80-4.90 (1H, m), 3.75-3.90 (2H, m), 2.73-2.82 (1H, m), 2.58-2.66 (1H, m), 2.40-2.45 (3H, m), 2.28-2.32 (6H, m)

Mass spectrometric value (ESI-MS) 629 (M−1)

Compound 725 N-[4-Bromo-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-4-({[2-hydroxy-2-(4-hydroxy-phenyl)-ethyl]-methyl-amino}-methyl)-benzamide

The title compound 725 was produced in the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 8.61 (1H, d, J=8.0 Hz), 8.36 (1H, s), 8.07 (1H, d, J=2.2 Hz), 7.92 (2H, d, J=2.2 Hz), 7.56 (1H, dd, J=2.2 Hz, J=9.0 Hz), 7.70 (1H, d, J=9.3 Hz), 7.60 (1H, d, J=7.8 Hz), 7.42-7.49 (3H, m), 7.10-7.24 (3H, m), 6.75 (2H, d, J=8.6 Hz), 4.70-4.75 (1H, m), 3.68 (2H, d, J=4.4 Hz), 2.67 (1H, dd, J=12.7 Hz, J=8.5 Hz), 2.50 (1H, dd, J=4.9 Hz, J=12.7 Hz), 2.33 (3H, s)

Mass spectrometric value (ESI-MS) 619 (M−1)

Compound 726 N-[4-Bromo-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-({[2-hydroxy-2-(4-hydroxy-phenyl)-ethyl]-methyl-amino}-methyl)-benzamide

The title compound 726 was produced in the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 8.61 (1H, d, J=9.0 Hz), 8.40 (1H, s), 8.34 (1H, s), 8.04-8.10 (2H, m), 7.90-7.95 (2H, m), 7.77 (1H, dd, J=9.0 Hz, J=2.4 Hz), 7.69 (1H, d, J=8.3 Hz), 7.45 (2H, d, J=8.3 Hz), 7.13 (2H, d, J=8.6 Hz), 6.75 (2H, d, J=8.6 Hz), 4.70-4.80 (1H, m), 3.70 (2H, d, J=4.4 Hz), 2.68 (1H, dd, J=8.3 Hz, J=12.8 Hz), 2.52 (1H, dd, J=4.6 Hz, J=12.7 Hz), 2.36 (3H, s)

Mass spectrometric value (ESI-MS) 701, 703 (M−1)

Compound 727 N-[4-Bromo-2-(3-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-4-({[2-hydroxy-2-(4-hydroxy-phenyl)-ethyl]-methyl-amino}-methyl)-benzamide

The title compound 727 was produced in the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 8.63 (1H, d, J=9.0 Hz), 8.34 (1H, s), 8.07 (1H, d, J=2.4 Hz), 7.94 (2H, d, J=8.3 Hz), 7.75 (1H, dd, J=8.8 Hz, J=2.2 Hz), 7.61 (1H, bs), 7.44 (2H, d, J=8.3 Hz), 7.26-7.36 (2H, m), 7.13 (2H, d, J=8.3 Hz), 6.97-7.03 (1H, m), 6.76 (2H, d, J=8.6 Hz), 4.72-4.82 (1H, m), 3.84 (3H, s), 3.76 (2H, d, J=5.8 Hz), 2.72 (1H, dd, J=8.6 Hz, J=13.0 Hz), 2.41 (3H, s), 2.57 (1H, dd, J=4.9 Hz, J=13.0 Hz)

Mass spectrometric value (ESI-MS) 629 (M−1)

Compound 728 N-[4-Bromo-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-[4-(2-morpholin-4-yl-2-oxo-ethyl)-piperazin-1-ylmethyl]-benzamide

The title compound 728 was produced in the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 8.49 (1H, d, J=9.0 Hz), 8.41 (1H, s), 7.97 (2H, d, J=7.8 Hz), 7.73 (1H, s), 7.68 (1H, d, J=7.6 Hz), 7.51 (1H, d, J=7.8 Hz), 7.41 (2H, d, J=7.8 Hz), 7.19-7.23 (3H, m), 3.47-3.75 (10H, m), 3.16 (2H, s), 2.40-2.56 (8H, m), 2.36 (3H, s)

Mass spectrometric value (ESI-MS) 659 (M−1)

Compound 729 N-[4-Bromo-2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-[4-(2-morpholin-4-yl-2-oxo-ethyl)-piperazin-1-ylmethyl]-benzamide

The title compound 729 was produced in the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 8.48 (1H, d, J=8.8 Hz), 8.42 (1H, s), 7.97 (2H, d, J=7.8 Hz), 7.66-7.75 (2H, m), 7.49-7.56 (2H, m), 7.41 (2H, d, J=7.8 Hz), 7.20-7.32 (2H, m), 3.48-3.76 (10H, m), 3.16 (2H, s), 2.40-2.56 (8H, m), 2.38 (3H, s)

Mass spectrometric value (ESI-MS) 661 (M−1)

Compound 730 N-[4-Bromo-2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-4-[4-(2-morpholin-4-yl-2-oxo-ethyl)-piperazin-1-ylmethyl]-benzamide

The title compound 730 was produced in the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 8.48 (1H, d, J=9.0 Hz), 8.43 (1H, s), 7.97 (2H, d, J=7.8 Hz), 7.76-7.87 (2H, m), 7.68-7.73 (1H, m), 7.49-7.57 (1H, m), 7.42 (2H, d, J=7.8 Hz), 7.11 (2H, dd, J=8.5 Hz, J=8.5 Hz), 3.49-3.76 (10H, m), 3.16 (2H, s), 2.40-2.65 (8H, m)

Mass spectrometric value (ESI-MS) 665 (M−1)

Compound 731 N-[4-Bromo-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-4-[4-(2-morpholin-4-yl-2-oxo-ethyl)-piperazin-1-ylmethyl]-benzamide

The title compound 731 was produced in the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 8.42-8.52 (2H, m), 7.96 (2H, d, J=7.8 Hz), 7.73 (1H, s), 7.46-7.60 (3H, m), 7.33-7.44 (3H, m), 7.11 (1H, ddd, J=2.4 Hz, J=8.3 Hz, J=8.3 Hz), 3.48-3.76 (10H, m), 3.15 (2H, s), 2.40-2.60 (8H, m)

Mass spectrometric value (ESI-MS) 665 (M−1)

Compound 732 N-[4-Bromo-2-(3-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-4-[4-(2-morpholin-4-yl-2-oxo-ethyl)-piperazin-1-ylmethyl]-benzamide

The title compound 732 was produced in the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 8.50 (2H, s, J=9.0 Hz), 8.45 (1H, s), 7.95 (2H, d, J=7.8 Hz), 7.78 (1H, s), 7.51 (1H, d, J=8.8 Hz), 7.25-7.43 (3H, m), 6.90-7.00 (2H, m), 3.83 (3H, s), 3.48-3.75 (10H, m), 3.16 (2H, s), 2.40-2.60 (8H, m)

Mass spectrometric value (ESI-MS) 675, 677 (M−1)

Compound 733 4-{[Bis-(2-ethoxy-ethyl)-amino]-methyl}-N-[4-bromo-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 733 was produced in the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 8.36-8.46 (2H, m), 7.98 (2H, d, J=8.0 Hz), 7.66 (2H, d, J=10.0 Hz), 7.45-7.51 (4H, m), 7.17 (1H, d, J=8.1 Hz), 3.79 (2H, s), 3.52 (4H, t, J=6.1 Hz), 3.46 (4H, q, J=7.0 Hz), 2.76 (4H, t, J=6.0 Hz), 2.29 (3H, s), 2.27 (3H, s), 1.19 (6H, t, J=7.0 Hz)

Mass spectrometric value (ESI-MS) 622, 624 (M−1)

Compound 734 4-{[Bis-(2-ethoxy-ethyl)-amino]-methyl}-N-[4-bromo-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 734 was produced in the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 8.45 (1H, s), 8.36 (1H, d, J=8.8 Hz), 7.98 (2H, d, J=7.3 Hz), 7.65-7.71 (3H, m), 7.45-7.48 (3H, m), 7.20 (2H, d, J=7.8 Hz), 3.79 (2H, s), 3.53 (4H, t, J=6.2 Hz), 3.46 (4H, q, J=7.9 Hz), 2.76 (4H, t, J=6.1 Hz), 2.35 (3H, s), 1.19 (6H, t, J=7.1 Hz)

Mass spectrometric value (ESI-MS) 607, 609 (M−1)

Compound 735 4-{[Bis-(2-ethoxy-ethyl)-amino]-methyl}-N-[4-bromo-2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 735 was produced in the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 8.47 (1H, s), 8.34 (1H, d, J=8.8 Hz), 7.98 (2H, d, J=8.0 Hz), 7.68 (2H, d, J=8.3 Hz), 7.54 (1H, d, J=7.3 Hz), 7.42-7.50 (3H, m), 7.20-7.34 (2H, m), 3.78 (2H, s), 3.52 (4H, t, J=6.1 Hz), 3.46 (4H, q, J=7.0 Hz), 2.76 (4H, t, J=6.2 Hz), 2.38 (3H, s), 1.19 (6H, t, J=7.0 Hz)

Mass spectrometric value (ESI-MS) 609 (M−1)

Compound 736 4-{[Bis-(2-ethoxy-ethyl)-amino]-methyl}-N-[4-bromo-2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 736 was produced in the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 8.48 (1H, s), 8.31 (1H, d, J=8.8 Hz), 7.98 (2H, d, J=8.0 Hz), 7.81 (2H, dd, J=6.5 Hz, J=6.5 Hz), 7.64 (1H, s), 7.42-7.51 (3H, m), 7.10 (2H, dd, J=8.7 Hz, J=8.7 Hz), 3.79 (2H, s), 3.53 (4H, t, J=6.2 Hz), 3.67 (4H, q, J=7.0 Hz), 2.76 (4H, t, J=6.1 Hz), 1.19 (6H, t, J=6.9 Hz)

Mass spectrometric value (ESI-MS) 635 (M+23)

Compound 737 4-{[Bis-(2-ethoxy-ethyl)-amino]-methyl}-N-[4-bromo-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 737 was produced in the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 8.50 (1H, s), 8.29 (1H, d, J=8.8 Hz), 7.98 (2H, d, J=8.0 Hz), 7.30-7.76 (7H, m), 7.11 (1H, ddd, J=2.0 Hz, J=8.3 Hz, J=8.3 Hz), 3.80 (2H, s), 3.53 (4H, t, J=6.2 Hz), 3.47 (4H, q, J=6.2 Hz), 2.76 (4H, t, J=6.2 Hz), 1.19 (6H, t, J=6.9 Hz)

Mass spectrometric value (ESI-MS) 635 (M+23)

Compound 738 4-{[Bis-(2-ethoxy-ethyl)-amino]-methyl}-N-[4-bromo-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 738 was produced in the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 8.55 (1H, s), 8.24 (1H, d, J=8.0 Hz), 8.07 (1H, s), 7.95-8.04 (3H, m), 7.62 (1H, s), 7.57 (1H, d, J=8.3 Hz), 7.50 (2H, d, J=8.3 Hz), 7.43 (1H, d, J=8.6 Hz), 3.81 (2H, s), 3.53 (4H, t, J=6.1 Hz), 3.47 (4H, q, J=7.0 Hz), 2.76 (4H, t, J=6.0 Hz), 1.19 (6H, t, J=7.1 Hz)

Mass spectrometric value (ESI-MS) 721 (M+23)

Compound 739 4-{[Bis-(2-ethoxy-ethyl)-amino]-methyl}-N-[4-bromo-2-(4-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 739 was produced in the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 8.53 (1H, d, J=9.0 Hz), 8.35-8.45 (1H, m), 7.96 (2H, dd, J=7.6 Hz, 7.6 Hz), 7.75 (1H, d, J=8.5 Hz), 7.67 (1H, s), 7.53 (1H, ddd, J=1.9 Hz, J=8.8 Hz, J=8.8 Hz), 7.42-7.50 (3H, m), 5.92 (2H, d, J=8.8 Hz), 3.83 (3H, s), 3.78 (2H, s), 3.52 (4H, t, J=6.1 Hz), 3.46 (4H, q, J=7.1 Hz), 2.75 (4H, t, J=5.5 Hz), 1.19 (6H, t, J=7.1 Hz)

Mass spectrometric value (ESI-MS) 625 (M−1)

Compound 740 4-{[Bis-(2-ethoxy-ethyl)-amino]-methyl}-N-[4-bromo-2-(3-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 740 was produced in the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 8.47 (1H, s), 8.36 (1H, d, J=8.8 Hz), 7.97 (2H, d, J=8.8 Hz), 7.68 (1H, s), 7.47 (3H, d, J=8.1 Hz), 7.37 (1H, s), 7.27-7.34 (2H, m), 6.92-6.98 (1H, m), 3.85 (3H, s), 3.78 (2H, s), 3.52 (4H, t, J=6.1 Hz), 3.46 (4H, q, J=7.0 Hz), 2.75 (4H, t, J=6.0 Hz), 1.18 (6H, t, J=7.0 Hz)

Mass spectrometric value (ESI-MS) 649 (M+23)

Compound 741 N-[4-Bromo-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-[4-(2-hydroxy-ethyl)-piperidin-1-ylmethyl]-benzamide

The title compound 741 was produced in the same manner as in Example 8.

¹H-NMR (DMSO-d₆, 400 MHz): δ 8.51 (1H, d, J=9.0 Hz), 8.41 (1H, s), 8.09 (1H, d, J=2.2 Hz), 7.89 (2H, d, J=8.0 Hz), 7.81 (1H, dd, J=2.4 Hz, J=9.0 Hz), 7.65 (2H, d, J=8.3 Hz), 7.49 (2H, d, J=8.0 Hz), 7.29 (2H, d, J=7.8 Hz), 4.29 (1H, t, J=5.1 Hz), 3.52 (2H, bs), 3.38-3.46 (2H, m), 2.78 (2H, d, J=11.0 Hz), 2.36 (3H, s), 1.92 (2H, t, J=11.1 Hz), 1.61 (2H, d, J=6.1 Hz), 1.30-1.40 (3H, m), 1.10-1.20 (2H, m)

Mass spectrometric value (ESI-MS) 577 (M−1)

Compound 742 N-[4-Bromo-2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-[4-(2-hydroxy-ethyl)-piperidin-1-ylmethyl]-benzamide

The title compound 742 was produced in the same manner as in Example 8.

¹H-NMR (DMSO-d₆, 400 MHz): δ 8.51 (1H, d, J=8.8 Hz), 8.41 (1H, s), 8.10 (1H, d, J=8.3 Hz), 7.88 (2H, d, J=2.2 Hz), 7.81 (1H, dd, J=2.2 Hz, J=9.0 Hz), 7.59 (1H, s), 7.53 (1H, d, J=7.6 Hz), 7.49 (3H, d, J=7.6 Hz), 7.36 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.28 (1H, d, J=7.6 Hz), 4.29 (1H, t, J=5.1 Hz), 3.52 (2H, bs), 3.38-3.45 (2H, m), 2.77 (2H, d, J=11.2 Hz), 2.37 (3H, s), 1.92 (2H, t, J=10.6 Hz), 1.60 (2H, d, J=6.1 Hz), 1.30-1.40 (3H, m), 1.10-1.21 (2H, m)

Mass spectrometric value (ESI-MS) 575 (M−1)

Compound 743 N-[4-Bromo-2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-4-[4-(2-hydroxy-ethyl)-piperidin-1-ylmethyl]-benzamide

The title compound 743 was produced in the same manner as in Example 8.

¹H-NMR (DMSO-d₆, 400 MHz): δ 8.50 (1H, d, J=9.0 Hz), 8.45 (1H, s), 8.09 (1H, d, J=2.4 Hz), 7.88 (2H, d, J=8.0 Hz), 7.78-7.85 (3H, m), 7.49 (2H, d, J=8.3 Hz), 7.32 (2H, dd, J=8.8 Hz, J=8.8 Hz), 4.29 (1H, t, J=5.1 Hz), 3.52 (2H, bs), 3.38-3.45 (2H, m), 2.77 (2H, d, J=11.2 Hz), 1.92 (2H, t, J=10.7 Hz), 1.60 (2H, d, J=6.1 Hz), 1.30-1.40 (3H, m), 1.10-1.20 (2H, m)

Mass spectrometric value (ESI-MS) 581 (M−1)

Compound 744 N-[4-Bromo-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-4-[4-(2-hydroxy-ethyl)-piperidin-1-ylmethyl]-benzamide

The title compound 744 was produced in the same manner as in Example 8.

¹H-NMR (DMSO-d₆, 400 MHz): δ 8.49 (1H, d, J=8.8 Hz), 8.44 (1H, s), 8.09 (1H, d, J=2.2 Hz), 7.88 (2H, d, J=8.0 Hz), 7.78-7.84 (1H, m), 7.47-7.63 (5H, m), 7.25-7.35 (1H, m), 4.27 (1H, t, J=5.1 Hz), 3.52 (2H, s), 3.35-3.46 (2H, m), 2.77 (2H, d, J=11.2 Hz), 1.92 (2H, dd, J=11.0 Hz, J=11.0 Hz), 1.61 (2H, d, J=11.7 Hz), 1.30-1.40 (3H, m), 1.08-1.22 (2H, m)

Mass spectrometric value (ESI-MS) 580 (M−1), 583 (M+1)

Compound 745 N-[4-Bromo-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-[4-(2-hydroxy-ethyl)-piperidin-1-ylmethyl]-benzamide

The title compound 745 was produced in the same manner as in Example 8.

¹H-NMR (DMSO-d₆, 400 MHz): δ 8.49 (1H, s), 8.44 (1H, d, J=8.8 Hz), 8.18 (1H, s), 8.05-8.10 (2H, m), 7.88 (2H, d, J=8.1 Hz), 7.79-7.85 (2H, m), 7.49 (2H, d, J=8.1 Hz), 4.29 (1H, bs), 3.52 (2H, bs), 3.38-3.45 (2H, m), 2.78 (2H, d, J=11.2 Hz), 1.86-2.00 (2H, m), 1.60 (2H, d, J=12.2 Hz), 1.30-1.40 (3H, m), 1.08-1.22 (2H, m)

Mass spectrometric value (ESI-MS) 667 (M+1)

Compound 746 N-[4-Bromo-2-(3-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-4-[4-(2-hydroxy-ethyl)-piperidin-1-ylmethyl]-benzamide

The title compound 746 was produced in the same manner as in Example 8.

¹H-NMR (DMSO-d₆, 400 MHz): δ 8.48 (1H, d, J=8.8 Hz), 8.42 (1H, s), 8.09 (1H, d, J=2.0 Hz), 7.88 (2H, d, J=8.0 Hz), 7.78-7.83 (1H, m), 7.49 (2H, d, J=9.0 Hz), 7.39 (1H, dd, J=7.8 Hz, J=7.8 Hz), 7.28-7.33 (2H, m), 7.00-7.07 (1H, m), 4.29 (1H, t, J=5.0 Hz), 3.82 (3H, s), 3.52 (2H, bs), 3.37-3.46 (2H, m), 2.77 (2H, d, J=10.8 Hz), 1.86-1.98 (2H, m), 1.60 (2H, d, J=12.2 Hz), 1.30-1.40 (3H, m), 1.08-1.22 (2H, m)

Mass spectrometric value (ESI-MS) 593 (M−1)

Compound 747 N-[4-Bromo-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-[(2-morpholin-4-yl-1-phenyl-ethylamino)-methyl]-benzamide

The title compound 747 was produced in the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 8.51 (1H, s), 8.33 (1H, d, J=8.0 Hz), 8.06 (1H, s), 7.99 (3H, d, J=7.8 Hz), 7.65 (1H, bs), 7.58 (1H, d, J=8.3 Hz), 7.49 (1H, d, J=7.6 Hz), 7.26-7.43 (7H, m), 3.84 (1H, d, J=14.2 Hz), 3.64-3.78 (6H, m), 3.57 (1H, d, J=14.2 Hz), 2.43-2.60 (3H, m), 2.29-2.40 (3H, m)

Mass spectrometric value (ESI-MS) 742 (M−1)

Compound 748 N-[4-Bromo-2-(4-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-4-[(2-morpholin-4-yl-1-phenyl-ethylamino)-methyl]-benzamide

The title compound 748 was produced in the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 8.44 (1H, d, J=8.8 Hz), 8.37 (1H, s), 7.99 (2H, d, J=7.8 Hz), 7.74 (2H, d, J=8.3 Hz), 7.69 (1H, s), 7.50 (1H, d, J=7.8 Hz), 7.34-7.42 (6H, m), 7.26-7.32 (1H, m), 6.91 (2H, d, J=8.8 Hz), 3.80-3.85 (1H, m), 3.82 (3H, s), 3.60-3.76 (5H, m), 3.50-3.57 (1H, m), 2.40-2.60 (3H, m), 2.28-2.34 (3H, m)

Mass spectrometric value (ESI-MS) 668 (M−1)

Compound 749 6-Bromo-2-{4-[(1,2-diethyl-pyrazolidin-4-ylamino)-methyl]-phenyl}-3-[(3,4-dimethyl-benzylidene)-amino]-3H-quinazolin-4-one

The title compound 749 was produced in the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 8.89 (1H, d, J=8.8 Hz), 8.73 (1H, s), 8.57 (1H, s), 8.03 (2H, d, J=8.0 Hz), 7.40-7.82 (5H, m), 7.10-7.25 (1H, m), 3.91 (2H, s), 3.56-3.70 (1H, m), 3.15-3.27 (2H, m), 2.70-2.85 (6H, m), 2.34 (6H, s), 1.11 (6H, t, J=7.1 Hz)

Mass spectrometric value (ESI-MS) 589 (M+1)

Compound 750 N-[4-Bromo-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-[(1,2-diethyl-pyrazolidin-4-ylamino)-methyl]-benzamide

The title compound 750 was produced in the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 8.42 (1H, d, J=9.0 Hz), 8.38 (1H, s), 7.99 (2H, d, J=8.1 Hz), 7.70 (1H, s), 7.62 (1H, s), 7.40-7.52 (4H, m), 7.15 (1H, d, J=7.8 Hz), 3.83 (2H, s), 3.56 (1H, tt, J=6.5 Hz, J=6.5 Hz), 3.12-3.20 (2H, m), 2.65-2.74 (6H, m), 2.28 (3H, s), 2.26 (3H, s), 1.09 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 605 (M−1)

Compound 751 6-Bromo-2-{4-[(1,2-diethyl-pyrazolidin-4-ylamino)-methyl]-phenyl}-3-[(3-fluoro-benzylidene)-amino]-3H-quinazolin-4-one

The title compound 751 was produced in the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 8.90 (1H, d, J=8.8 Hz), 8.74 (1H, s), 8.59 (1H, s), 8.02 (2H, d, J=8.3 Hz), 7.42-7.65 (6H, m), 7.21 (1H, ddd, J=1.7 Hz, J=8.3 Hz, J=8.3 Hz), 3.89 (2H, s), 3.62 (1H, tt, J=6.4 Hz, J=6.4 Hz), 3.15-3.23 (2H, m), 2.65-2.80 (6H, m), 1.10 (6H, t, J=7.2 Hz)

Compound 752 N-[4-Bromo-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-4-[(1,2-diethyl-pyrazolidin-4-ylamino)-methyl]-benzamide

The title compound 752 was produced in the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 8.46 (1H, s), 8.34 (1H, d, J=8.8 Hz), 7.99 (2H, d, J=7.8 Hz), 7.66 (1H, s), 7.34-7.62 (6H, m), 7.11 (1H, ddd, J=2.0 Hz, J=8.3 Hz, J=8.3 Hz), 3.85 (2H, s), 3.57 (1H, tt, J=6.5 Hz, J=6.5 Hz), 3.12-3.20 (2H, m), 2.64-2.74 (6H, m), 1.10 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 595 (M−1)

Compound 753 6-Bromo-3-[(4-chloro-3-trifluoromethyl-benzylidene)-amino]-2-{4-[(1,2-diethyl-pyrazolidin-4-ylamino)-methyl]-phenyl}-3H-quinazolin-4-one

The title compound 753 was produced in the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 8.88 (1H, d, J=8.8 Hz), 8.75 (1H, s), 8.58 (1H, s), 7.92-8.05 (2H, m), 7.45-7.70 (6H, m), 3.89 (2H, s), 3.54-3.65 (1H, m), 3.12-3.22 (2H, m), 2.65-2.76 (6H, m), 1.10 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 663 (M−1)

Compound 754 N-[4-Bromo-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-[(1,2-diethyl-pyrazolidin-4-ylamino)-methyl]-benzamide

The title compound 754 was produced in the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 8.51 (1H, s), 8.31 (1H, d, J=8.1 Hz), 8.06 (1H, s), 7.99 (3H, d, J=7.8 Hz), 7.65 (1H, s), 7.58 (1H, d, J=8.3 Hz), 7.47 (3H, d, J=8.3 Hz), 3.86 (2H, s), 3.58 (1H, tt, J=6.3 Hz, J=6.3 Hz), 3.12-3.20 (2H, m), 2.65-2.75 (6H, m), 1.10 (6H, t, J=7.1 Hz)

Mass spectrometric value (ESI-MS) 681 (M+1)

Compound 755 6-Bromo-2-{4-[(1,2-diethyl-pyrazolidin-4-ylamino)-methyl]-phenyl}-3-[(4-methoxy-benzylidene)-amino]-3H-quinazolin-4-one

The title compound 755 was produced in the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 8.89 (1H, d, J=8.5 Hz), 8.71 (1H, s), 8.58 (1H, s), 8.03 (2H, d, J=8.3 Hz), 7.79 (2H, d, J=8.8 Hz), 7.60 (1H, d, J=2.2 Hz), 7.57 (1H, s), 7.49 (2H, d, J=8.3 Hz), 7.00 (2H, d, J=8.8 Hz), 3.89 (5H, s), 3.62 (1H, tt, J=6.2 Hz, J=6.2 Hz), 3.15-3.25 (2H, m), 2.65-2.80 (6H, m), 1.11 (6H, t, J=7.2 Hz)

Compound 756 N-[4-Bromo-2-(4-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-4-[(1,2-diethyl-pyrazolidin-4-ylamino)-methyl]-benzamide

The title compound 756 was produced in the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 8.46 (1H, d, J=8.8 Hz), 8.37 (1H, s), 7.98 (2H, d, J=7.8 Hz), 7.67-7.76 (3H, m), 7.49 (1H, d, J=7.6 Hz), 7.42 (2H, d, J=8.3 Hz), 6.91 (2H, d, J=8.8 Hz), 3.83 (2H, s), 3.82 (3H, s), 3.57 (1H, tt, J=6.3 Hz, J=6.3 Hz), 3.12-3.20 (2H, m), 2.65-2.75 (6H, m), 1.10 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 607 (M−1)

Compound 757 N-[4-Bromo-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-{[3-(methyl-phenyl-amino)-propylamino]-methyl}-benzamide

The title compound 757 was produced in the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 8.35-8.45 (2H, m), 7.96 (2H, d, J=7.8 Hz), 7.71 (1H, s), 7.60 (1H, s), 7.43-7.48 (2H, m), 7.40 (2H, d, J=8.3 Hz), 7.17-7.23 (2H, m), 7.14 (1H, d, J=7.8 Hz), 6.65-6.73 (3H, m), 3.83 (2H, s), 3.38 (2H, t, J=7.2 Hz), 2.89 (3H, s), 2.68 (2H, t, J=7.0 Hz), 2.26 (3H, s), 2.25 (3H, s), 1.81 (2H, tt, J=7.1 Hz, J=7.1 Hz)

Mass spectrometric value (ESI-MS) 626 (M−1), 628 (M+1)

Compound 758 N-[4-Bromo-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-{[3-(methyl-phenyl-amino)-propylamino]-methyl}-benzamide

The title compound 758 was produced in the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 8.37-8.44 (2H, m), 7.92-7.79 (2H, m), 7.64-7.72 (3H, m), 7.45 (1H, d, J=8.0 Hz), 7.39 (2H, d, J=8.0 Hz), 7.16-7.23 (4H, m), 6.65-6.74 (3H, m), 3.82 (2H, s), 3.39 (2H, t, J=7.2 Hz), 2.89 (3H, s), 2.67 (2H, t, J=6.8 Hz), 2.34 (3H, s), 1.80 (2H, tt, J=7.0 Hz, J=7.0 Hz)

Mass spectrometric value (ESI-MS) 612 (M−1), 614 (M+1)

Compound 759 N-[4-Bromo-2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-4-{[3-(methyl-phenyl-amino)-propylamino]-methyl}-benzamide

The title compound 759 was produced in the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 8.37-8.46 (2H, m), 7.98 (2H, d, J=7.8 Hz), 7.81 (2H, bs), 7.66 (1H, s), 7.50 (1H, d, J=8.6 Hz), 7.43 (2H, d, J=8.1 Hz), 7.19-7.24 (2H, m), 7.11 (2H, dd, J=8.7 Hz, J=8.7 Hz), 6.66-6.75 (3H, m), 3.84 (2H, s), 3.41 (2H, t, J=7.2 Hz), 2.92 (3H, s), 2.69 (2H, t, J=7.0 Hz), 1.81 (2H, tt, J=7.0 Hz, J=7.0 Hz)

Mass spectrometric value (ESI-MS) 616 (M−1), 618 (M+1)

Compound 760 N-[4-Bromo-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-4-{[3-(methyl-phenyl-amino)-propylamino]-methyl}-benzamide

The title compound 760 was produced in the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 8.45 (1H, bs), 8.34 (1H, d, J=8.5 Hz), 7.98 (2H, d, J=7.8 Hz), 7.34-7.67 (7H, m), 7.18-7.25 (2H, m), 7.11 (1H, ddd, J=1.7 Hz, J=7.6 Hz, J=7.6 Hz), 6.72 (2H, d, J=7.8 Hz), 6.68 (1H, dd, J=7.2 Hz, J=7.2 Hz), 3.84 (2H, s), 3.41 (2H, t, J=7.2 Hz), 2.91 (3H, s), 2.68 (2H, t, J=7.0 Hz), 1.80 (2H, tt, J=7.0 Hz, J=7.0 Hz)

Mass spectrometric value (ESI-MS) 614 (M−1), 618 (M+1)

Compound 761 N-[4-Bromo-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-{[3-(methyl-phenyl-amino)-propylamino]-methyl}-benzamide

The title compound 761 was produced in the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 8.50 (1H, s), 8.27 (1H, d, J=8.0 Hz), 8.06 (1H, s), 7.99 (2H, d, J=7.6 Hz), 7.63 (1H, bs), 7.56 (1H, d, J=8.3 Hz), 7.45 (2H, d, J=8.1 Hz), 7.19-7.25 (2H, m), 6.65-6.75 (5H, m), 3.85 (2H, s), 3.41 (2H, t, J=7.1 Hz), 2.92 (3H, s), 2.69 (2H, t, J=7.0 Hz), 1.81 (2H, tt, J=7.0 Hz, J=7.0 Hz)

Mass spectrometric value (ESI-MS) 698, 700 (M−1), 702 (M+1)

Compound 762 N-[4-Bromo-2-(4-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-4-{[3-(methyl-phenyl-amino)-propylamino]-methyl}-benzamide

The title compound 762 was produced in the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 8.44 (1H, d, J=8.8 Hz), 8.37 (1H, s), 7.97 (2H, d, J=8.0 Hz), 7.65-7.77 (3H, m), 7.48 (1H, d, J=8.8 Hz), 7.40 (2H, d, J=8.0 Hz), 7.19-7.25 (3H, m), 6.90 (2H, d, J=8.8 Hz), 6.71 (2H, d, J=8.0 Hz), 6.68 (1H, dd, J=7.2 Hz, J=7.2 Hz), 3.81 (2H, s), 3.81 (3H, s), 3.40 (2H, t, J=7.1 Hz), 2.91 (3H, s), 2.67 (2H, t, J=7.0 Hz), 1.79 (2H, tt, J=7.0 Hz, J=7.0 Hz)

Mass spectrometric value (ESI-MS) 626 (M−1), 630 (M+1)

Compound 763 N-[4-Bromo-2-(3-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-4-{[3-(methyl-phenyl-amino)-propylamino]-methyl}-benzamide

The title compound 763 was produced in the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 8.44 (1H, d, J=9.0 Hz), 8.40 (1H, s), 7.97 (2H, d, J=7.8 Hz), 7.71 (1H, s), 7.18-7.54 (8H, m), 6.94-7.00 (1H, m), 6.71 (2H, d, J=8.0 Hz), 6.68 (1H, dd, J=7.2 Hz, J=7.2 Hz), 3.84 (3H, s), 3.82 (2H, s), 3.40 (2H, t, J=7.1 Hz), 2.91 (3H, s), 2.67 (2H, t, J=6.8 Hz), 1.80 (2H, tt, J=7.0 Hz, J=7.0 Hz),

Mass spectrometric value (ESI-MS) 626 (M−1), 630 (M+1)

Compound 764 N-[4-Bromo-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-[(2-ethylsulfanyl-ethylamino)-methyl]-benzamide

The title compound 764 was produced in the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 8.37-8.45 (2H, m), 7.98 (2H, d, J=7.8 Hz), 7.72 (1H, s), 7.60 (1H, s), 7.42-7.50 (4H, m), 7.07-7.20 (2H, m), 3.88 (2H, s), 2.83 (2H, t, J=6.2 Hz), 2.73 (2H, t, J=6.6 Hz), 2.51 (2H, q, J=7.3 Hz), 2.26 (3H, s), 2.25 (3H, s), 1.24 (3H, t, J=7.4 Hz)

Mass spectrometric value (ESI-MS) 565 (M−1)

Compound 765 N-[4-Bromo-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-[(2-ethylsulfanyl-ethylamino)-methyl]-benzamide

The title compound 765 was produced in the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 8.39-8.45 (2H, m), 7.84-8.02 (2H, m), 7.68 (2H, d, J=8.5 Hz), 7.42-7.50 (3H, m), 7.15-7.25 (3H, m), 3.88 (2H, s), 2.83 (2H, t, J=6.3 Hz), 2.73 (2H, t, J=6.3 Hz), 2.52 (2H, q, J=7.4 Hz), 2.36 (3H, s), 1.25 (3H, t, J=7.4 Hz)

Mass spectrometric value (ESI-MS) 551 (M−1)

Compound 766 N-[4-Bromo-2-(3-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-[(2-ethylsulfanyl-ethylamino)-methyl]-benzamide

The title compound 766 was produced in the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 8.44 (1H, s), 8.37 (1H, d, J=8.8 Hz), 7.99 (2H, d, J=8.1 Hz), 7.68 (2H, s), 7.54 (1H, d, J=7.3 Hz), 7.42-7.50 (3H, m), 7.29 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.22 (1H, d, J=7.6 Hz), 3.87 (2H, s), 2.81 (2H, t, J=6.5 Hz), 2.72 (2H, t, J=6.2 Hz), 2.53 (2H, q, J=7.4 Hz), 2.37 (3H, s), 1.26 (3H, t, J=7.3 Hz)

Mass spectrometric value (ESI-MS) 551 (M−1)

Compound 767 N-[4-Bromo-2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-4-[(2-ethylsulfanyl-ethylamino)-methyl]-benzamide

The title compound 767 was produced in the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 8.46 (1H, s), 8.33 (1H, d, J=8.3 Hz), 7.98 (2H, d, J=7.8 Hz), 7.80 (2H, bs), 7.65 (1H, s), 7.45 (3H, d, J=8.0 Hz), 7.10 (2H, dd, J=8.5 Hz, J=8.5 Hz), 3.87 (2H, s), 2.82 (2H, t, J=6.3 Hz), 2.72 (2H, t, J=6.5 Hz), 2.53 (2H, q, J=7.4 Hz), 1.26 (3H, t, J=7.3 Hz)

Mass spectrometric value (ESI-MS) 557 (M−1)

Compound 768 N-[4-Bromo-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-4-[(2-ethylsulfanyl-ethylamino)-methyl]-benzamide

The title compound 768 was produced in the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 8.46 (1H, bs), 8.34 (1H, d, J=7.8 Hz), 7.99 (2H, d, J=7.6 Hz), 7.66 (1H, bs), 7.34-7.60 (6H, m), 7.11 (1H, ddd, J=2.4 Hz, J=8.3 Hz, J=8.3 Hz), 3.89 (2H, s), 2.83 (2H, t, J=6.4 Hz), 2.73 (2H, t, J=6.3 Hz), 2.54 (2H, q, J=7.4 Hz), 1.26 (3H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 555 (M−1)

Compound 769 N-[4-Bromo-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-[(2-ethylsulfanyl-ethylamino)-methyl]-benzamide

The title compound 769 was produced in the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 8.53 (1H, s), 8.27 (1H, d, J=6.8 Hz), 8.06 (1H, s), 7.99 (3H, d, J=7.8 Hz), 7.63 (1H, bs), 7.57 (1H, d, J=8.3 Hz), 7.40-7.50 (3H, m), 3.90 (2H, s), 2.84 (2H, t, J=6.2 Hz), 2.73 (2H, t, J=6.5 Hz), 2.54 (2H, q, J=7.4 Hz), 1.27 (3H, t, J=7.5 Hz)

Mass spectrometric value (ESI-MS) 643 (M−1)

Compound 770 N-[4-Bromo-2-(4-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-4-[(2-ethylsulfanyl-ethylamino)-methyl]-benzamide

The title compound 770 was produced in the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 8.37-8.45 (2H, m), 7.98 (2H, d, J=7.8 Hz), 7.68-7.74 (3H, m), 7.47 (1H, d, J=8.3 Hz), 7.42 (2H, d, J=8.0 Hz), 6.90 (2H, d, J=8.8 Hz), 3.86 (2H, s), 3.81 (3H, s), 2.81 (2H, t, J=6.5 Hz), 2.72 (2H, t, J=6.2 Hz), 2.52 (2H, q, J=7.4 Hz), 1.25 (3H, t, J=7.5 Hz)

Mass spectrometric value (ESI-MS) 569 (M−1)

Compound 771 N-[4-Bromo-2-(3-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-4-[(2-ethylsulfanyl-ethylamino)-methyl]-benzamide

The title compound 771 was produced in the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 8.45 (1H, s), 8.39 (1H, d, J=9.0 Hz), 7.97 (2H, d, J=7.8 Hz), 7.73 (1H, bs), 7.40-7.50 (3H, m), 7.34 (1H, s), 7.26-7.30 (2H, m), 6.90-7.00 (1H, m), 3.85 (2H, s), 3.83 (3H, s), 2.81 (2H, t, J=6.4 Hz), 2.71 (2H, t, J=6.2 Hz), 2.53 (2H, q, J=7.4 Hz), 1.25 (3H, t, J=7.4 Hz)

Mass spectrometric value (ESI-MS) 567 (M−1)

Compound 772 N-[4-Bromo-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-(4-pyridin-2-yl-piperazin-1-ylmethyl)-benzamide

The title compound 772 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 2.29 (3H, s), 2.30 (3H, s), 2.59 (4H, bs), 3.58 (4H, bs), 3.64 (2H, bs), 6.62 (2H, m), 7.18 (1H, d, J=7.8 Hz), 7.59 (7H, m), 8.00 (2H, d, J=8.1 Hz), 8.18 (1H, m), 8.31 (1H, s), 8.56 (1H, m), 10.08 (1H, bs), 11.68 (1H, s)

Mass spectrometric value (ESI-MS) 623 (M−1)

Compound 773 N-[4-Bromo-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-(4-pyridin-2-yl-piperazin-1-ylmethyl)-benzamide

The title compound 773 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 2.39 (3H, s), 2.59 (4H, bs), 3.58 (4H, bs), 3.64 (2H, bs), 6.63 (2H, m), 7.23 (2H, d, J=7.8 Hz), 7.59 (7H, m), 8.00 (2H, d, J=7.6 Hz), 8.18 (1H, m), 8.32 (1H, s), 8.60 (1H, d, J=8.8 Hz), 9.90 (1H, bs), 11.70 (1H, bs)

Mass spectrometric value (ESI-MS) 611 (M−1)

Compound 774 N-[4-Bromo-2-(4-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-4-(4-pyridin-2-yl-piperazin-1-ylmethyl)-benzamide

The title compound 774 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 2.59 (4H, bs), 3.59 (4H, bs), 3.65 (2H, bs), 6.63 (2H, m), 7.12 (2H, m), 7.64 (7H, m), 8.00 (2H, d, J=7.8 Hz), 8.18 (1H, m), 8.37 (1H, bs), 8.60 (1H, m), 10.20 (1H, bs), 11.70 (1H, bs)

Mass spectrometric value (ESI-MS) 613 (M−1)

Compound 775 N-[4-Bromo-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-4-(4-pyridin-2-yl-piperazin-1-ylmethyl)-benzamide

The title compound 775 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 2.59 (4H, bs), 3.58 (4H, bs), 3.65 (2H, bs), 6.63 (2H, m), 7.14 (1H, m), 7.50 (8H, m), 8.00 (2H, d, J=7.8 Hz), 8.18 (1H, m), 8.40 (1H, s), 8.55 (1H, bs), 10.30 (1H, bs), 11.60 (1H, bs)

Mass spectrometric value (ESI-MS) 613 (M−1)

Compound 776 N-[4-Bromo-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-4-(4-pyridin-2-yl-piperazin-1-ylmethyl)-benzamide

The title compound 776 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 2.60 (4H, bs), 3.58 (4H, bs), 3.65 (2H, bs), 6.63 (2H, m), 7.54 (6H, m), 8.02 (4H, m), 8.18 (1H, m), 8.47 (2H, bs), 10.45 (1H, bs), 11.50 (1H, bs)

Mass spectrometric value (ESI-MS) 697 (M−1)

Compound 777 N-[4-Bromo-2-(4-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-4-(4-pyridin-2-yl-piperazin-1-ylmethyl)-benzamide

The title compound 777 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 2.59 (4H, bs), 3.61 (6H, m), 3.84 (3H, s), 6.62 (2H, m), 6.93 (2H, d, J=8.8 Hz), 7.49 (4H, m), 7.72 (3H, m), 7.80 (2H, d, J=7.6 Hz), 8.18 (1H, m), 8.31 (1H, bs), 8.58 (1H, m), 9.99 (1H, bs), 11.69 (1H, bs)

Mass spectrometric value (ESI-MS) 625 (M−1)

Compound 778 N-[4-Bromo-2-(3-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-4-(4-pyridin-2-yl-piperazin-1-ylmethyl)-benzamide

The title compound 778 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 2.59 (4H, bs), 3.59 (6H, m), 3.86 (3H, s), 6.63 (2H, m), 6.98 (1H, m), 7.32 (3H, m), 7.54 (4H, m), 7.72 (1H, m), 8.00 (2H, d, J=7.3 Hz), 8.18 (1H, m), 8.34 (1H, bs), 8.60 (1H, d, J=8.8 Hz)

Mass spectrometric value (ESI-MS) 625 (M−1)

Compound 779 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[3-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-thiophen-2-yl]-benzamide

The title compound 779 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.10 (6H, m), 2.51 (4H, m), 3.88 (4H, m), 7.03 (1H, d, J=6.1 Hz), 7.53 (2H, m), 7.68 (2H, d, J=8.0 Hz), 7.92 (1H, d, J=7.8 Hz), 8.06 (2H, m), 8.32 (1H, bs), 8.39 (1H, s)

Mass spectrometric value (ESI-MS) 595 (M−1)

Compound 780 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[3-(4-methoxy-benzylidene-hydrazinocarbonyl)-thiophen-2-yl]-benzamide

The title compound 780 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 1.10 (6H, m), 2.51 (4H, m), 3.88 (7H, m), 7.00 (3H, m), 7.53 (2H, m), 7.68 (1H, m), 7.80 (2H, d, J=8.3 Hz), 7.93 (1H, d, J=7.1 Hz), 8.06 (1H, m), 8.31 (1H, s)

Mass spectrometric value (ESI-MS) 523 (M−1)

Compound 781 2-{3-[3-(3,4-Dimethyl-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-ylcarbamoyl]-benzylsulfanyl}-ethanesulfonic acid

The title compound 781 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 2.30 (6H, m), 2.47 (3H, s), 2.79 (2H, m), 2.98 (2H, m), 3.85 (2H, bs), 6.71 (1H, m), 7.18 (1H, d, J=7.6 Hz), 7.20-8.00 (6H, m), 8.23 (1H, bs)

Mass spectrometric value (ESI-MS) 544 (M−1)

Compound 782 2-{3-[4-Methyl-3-(4-methyl-benzylidene-hydrazinocarbonyl)-thiophen-2-ylcarbamoyl]-benzylsulfanyl}-ethanesulfonic acid

The title compound 782 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 2.39 (3H, s), 2.47 (3H, s), 2.79 (2H, m), 2.99 (2H, m), 3.84 (2H, s), 6.72 (1H, m), 7.20-7.94 (8H, m), 8.26 (1H, bs)

Mass spectrometric value (ESI-MS) 530 (M−1)

Compound 783 2-{3-[3-(4-Fluoro-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-ylcarbamoyl]-benzylsulfanyl}-ethanesulfonic acid

The title compound 783 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 2.47 (3H, bs), 2.80 (2H, m), 2.99 (2H, m), 3.84 (2H, bs), 6.72 (1H, m), 7.14 (2H, m), 7.49 (1H, m), 7.61 (1H, m), 7.92 (4H, m), 8.29 (1H, bs)

Mass spectrometric value (ESI-MS) 534 (M−1)

Compound 784 2-{3-[3-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-ylcarbamoyl]-benzylsulfanyl}-ethanesulfonic acid

The title compound 784 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 2.47 (3H, bs), 2.79 (2H, m), 2.98 (2H, m), 3.84 (2H, bs), 6.70 (1H, m), 7.40-8.02 (6H, m), 8.31 (2H, m)

Mass spectrometric value (ESI-MS) 618 (M−1)

Compound 785 2-{3-[3-(4-Methoxy-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-ylcarbamoyl]-benzylsulfanyl}-ethanesulfonic acid

The title compound 785 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 2.47 (3H, bs), 2.81 (2H, m), 2.98 (2H, m), 3.84 (5H, m), 6.71 (1H, m), 6.97 (2H, m), 7.44-7.98 (6H, m), 8.24 (1H, bs)

Mass spectrometric value (ESI-MS) 546 (M−1)

Compound 786 3-{[Bis-(2-hydroxy-ethyl)-amino]-methyl}-N-[3-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-benzamide

The title compound 786 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 2.30 (6H, m), 2.50 (3H, s), 2.69 (4H, t, J=5.9 Hz), 3.63 (4H, t, J=5.5 Hz), 3.81 (2H, s), 6.69 (1H, m), 7.19 (1H, m), 7.51 (2H, m), 7.65 (2H, m), 7.87 (1H, m), 7.98 (1H, s), 8.22 (1H, s)

Mass spectrometric value (ESI-MS) 507 (M−1)

Compound 787 3-{[Bis-(2-hydroxy-ethyl)-amino]-methyl}-N-[4-methyl-3-(4-methyl-benzylidene-hydrazinocarbonyl)-thiophen-2-yl]-benzamide

The title compound 787 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 2.38 (3H, s), 2.57 (3H, s), 2.78 (4H, t, J=5.1 Hz), 3.74 (4H, t, J=5.1 Hz), 3.84 (2H, s), 6.50 (1H, s), 7.19 (2H, d, J=8.0 Hz), 7.45 (2H, m), 7.70 (2H, d, J=7.8 Hz), 8.00 (1H, m), 8.08 (1H, s), 8.25 (1H, s), 9.16 (1H, s)

Mass spectrometric value (ESI-MS) 493 (M−1)

Compound 788 3-{[Bis-(2-hydroxy-ethyl)-amino]-methyl}-N-[3-(4-fluoro-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-benzamide

The title compound 788 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 2.54 (3H, s), 2.79 (4H, t, J=5.2 Hz), 3.74 (4H, t, J=5.1 Hz), 3.83 (2H, s), 6.48 (1H, s), 7.04 (2H, m), 7.45 (2H, m), 7.80 (2H, m), 8.00 (1H, m), 8.13 (1H, s), 8.26 (1H, s), 9.28 (1H, s), 13.16 (1H, bs)

Mass spectrometric value (ESI-MS) 497 (M−1)

Compound 789 3-{[Bis-(2-hydroxy-ethyl)-amino]-methyl}-N-[3-(3-fluoro-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-benzamide

The title compound 789 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 2.56 (3H, s), 2.79 (4H, t, J=5.0 Hz), 3.75 (4H, m), 3.84 (2H, s), 6.47 (1H, s), 7.04 (1H, m), 7.17-7.70 (5H, m), 8.01 (1H, m), 8.16 (1H, s), 8.29 (1H, s), 9.35 (1H, s), 13.20 (1H, bs)

Mass spectrometric value (ESI-MS) 497 (M−1)

Compound 790 3-{[Bis-(2-hydroxy-ethyl)-amino]-methyl}-N-[3-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-benzamide

The title compound 790 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 2.50 (3H, s), 2.72 (4H, t, J=5.8 Hz), 3.65 (4H, t, J=5.8 Hz), 3.84 (2H, s), 6.71 (1H, d, J=1.0 Hz), 7.51 (1H, m), 7.67 (2H, m), 7.85 (1H, m), 8.00 (2H, m), 8.33 (2H, m)

Mass spectrometric value (ESI-MS) 581 (M−1)

Compound 791 3-{[Bis-(2-hydroxy-ethyl)-amino]-methyl}-N-[3-(4-methoxy-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-benzamide

The title compound 791 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 2.55 (3H, s), 2.79 (4H, t, J=5.2 Hz), 3.74 (4H, m), 3.85 (5H, m), 6.51 (1H, s), 6.92 (2H, m), 7.45 (2H, m), 7.67 (1H, m), 7.77 (1H, m), 8.01 (1H, m), 8.05 (1H, s), 8.26 (1H, s), 9.09 (1H, s), 13.27 (1H, bs)

Mass spectrometric value (ESI-MS) 509 (M−1)

Compound 792 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[3-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-benzo[b]thiophen-2-yl]-benzamide

The title compound 792 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.13 (3H, d, J=2.2 Hz), 1.15 (3H, d, J=2.2 Hz), 2.26 (6H, m), 2.51 (2H, d, J=6.1 Hz), 2.63 (2H, m), 3.65-4.05 (4H, m), 7.12 (1H, m), 7.30 (1H, m), 7.40-7.51 (4H, m), 7.67 (1H, m), 7.86 (2H, m), 8.03 (1H, m), 8.18 (1H, s), 8.25 (1H, d, J=5.6 Hz), 9.44 (1H, s), 13.13 (1H, m)

Mass spectrometric value (ESI-MS) 571 (M−1)

Compound 793 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[3-(4-methyl-benzylidene-hydrazinocarbonyl)-benzo[b]thiophen-2-yl]-benzamide

The title compound 793 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.13 (6H, m), 2.39 (3H, s), 2.51 (2H, d, J=6.1 Hz), 2.64 (2H, m), 3.65-4.05 (4H, m), 7.19 (2H, d, J=8.0 Hz), 7.32 (1H, m), 7.42-7.50 (3H, m), 7.75 (2H, m), 7.86 (2H, m), 8.04 (1H, m), 8.19 (1H, m), 8.28 (1H, d, J=6.1 Hz), 9.40 (1H, s), 13.14 (1H, bs)

Mass spectrometric value (ESI-MS) 557 (M−1)

Compound 794 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[3-(4-fluoro-benzylidene-hydrazinocarbonyl)-benzo[b]thiophen-2-yl]-benzamide

The title compound 794 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.13 (6H, m), 2.51 (2H, d, J=6.1 Hz), 2.65 (2H, m), 3.63-4.08 (4H, m), 7.07 (2H, m), 7.29 (1H, m), 7.36-7.50 (3H, m), 7.85 (4H, m), 8.03 (1H, m), 8.26 (2H, m), 9.50 (1H, d, J=4.4 Hz), 13.13 (1H, bs)

Mass spectrometric value (ESI-MS) 561 (M−1)

Compound 795 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[3-(3-fluoro-benzylidene-hydrazinocarbonyl)-benzo[b]thiophen-2-yl]-benzamide

The title compound 795 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.15 (6H, m), 2.53 (2H, m), 2.67 (2H, m), 3.61-4.14 (4H, m), 7.01 (1H, m), 7.11-7.30 (3H, m), 7.45 (3H, m), 7.62-7.90 (3H, m), 7.99 (1H, m), 8.23 (1H, d, J=12.7 Hz), 8.35 (1H, d, J=6.1 Hz), 9.82 (1H, d, J=13.9 Hz), 13.10 (1H, s)

Mass spectrometric value (ESI-MS) 561 (M−1)

Compound 796 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[3-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-benzo[b]thiophen-2-yl]-benzamide

The title compound 796 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.14 (3H, d, J=6.1 Hz), 1.17 (3H, d, J=6.1 Hz), 2.50-2.80 (4H, m), 3.63-4.16 (4H, m), 7.06 (2H, m), 7.30 (1H, m), 7.44 (2H, m), 7.70 (1H, m), 7.80-8.07 (4H, m), 8.16 (1H, s), 8.53 (1H, s), 10.08 (1H, d, J=6.1 Hz), 13.10 (1H, d, J=1.0 Hz)

Mass spectrometric value (ESI-MS) 645 (M−1)

Compound 797 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[3-(4-methoxy-benzylidene-hydrazinocarbonyl)-benzo[b]thiophen-2-yl]-benzamide

The title compound 797 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.13 (6H, m), 2.51 (2H, d, J=6.1 Hz), 2.63 (2H, m), 3.64-4.06 (7H, m), 6.90 (2H, d, J=8.8 Hz), 7.31 (1H, m), 7.48 (3H, m), 7.83 (4H, m), 8.03 (1H, m), 8.18 (1H, m), 8.28 (1H, d, J=6.4 Hz), 9.38 (1H, s), 13.16 (1H, bs)

Mass spectrometric value (ESI-MS) 573 (M−1)

Compound 798 N-[3-(3,4-Dimethyl-benzylidene-hydrazinocarbonyl)-benzo[b]thiophen-2-yl]-3-(4-hydroxymethyl-piperidin-1-ylmethyl)-benzamide

The title compound 798 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.35 (2H, m), 1.51 (1H, m), 1.72 (2H, m), 2.05 (2H, m), 2.29 (3H, s), 2.30 (3H, s), 2.93 (2H, m), 3.50 (2H, d, J=6.1 Hz), 3.62 (2H, s), 7.18 (1H, d, J=7.8 Hz), 7.32 (1H, m), 7.47 (3H, m), 7.61 (1H, d, J=7.6 Hz), 7.66 (1H, s), 7.87 (2H, m), 7.97 (1H, m), 8.04 (1H, m), 8.17 (1H, m), 9.34 (1H, bs), 12.85 (1H, bs)

Mass spectrometric value (ESI-MS) 553 (M−1)

Compound 799 3-(4-Hydroxymethyl-piperidin-1-ylmethyl)-N-[3-(4-methyl-benzylidene-hydrazinocarbonyl)-benzo[b]thiophen-2-yl]-benzamide

The title compound 799 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.42 (2H, m), 1.52 (1H, m), 1.73 (2H, m), 2.12 (2H, m), 2.38 (3H, s), 3.00 (2H, m), 3.50 (2H, d, J=6.1 Hz), 3.70 (2H, s), 7.23 (2H, m), 7.32 (1H, m), 7.45 (2H, m), 7.64 (1H, d, J=7.8 Hz), 7.71 (2H, m), 8.86 (2H, m), 7.97 (1H, d, J=8.0 Hz), 8.03 (1H, m), 8.21 (1H, s), 9.40 (1H, bs), 12.84 (1H, bs)

Mass spectrometric value (ESI-MS) 539 (M−1)

Compound 800 N-[3-(4-Fluoro-benzylidene-hydrazinocarbonyl)-benzo[b]thiophen-2-yl]-3-(4-hydroxymethyl-piperidin-1-ylmethyl)-benzamide

The title compound 800 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.40-1.60 (3H, m), 1.73 (2H, m), 2.17 (2H, m), 3.05 (2H, m), 3.50 (2H, d, J=5.9 Hz), 3.75 (2H, s), 7.04 (1H, m), 7.11 (2H, m), 7.28 (1H, m), 7.37-7.50 (2H, m), 7.64 (1H, d, J=7.6 Hz), 7.83 (2H, m), 7.94 (1H, m), 8.01 (1H, s), 8.07 (1H, m), 8.26 (1H, s), 9.50 (1H, bs), 12.73 (1H, bs)

Mass spectrometric value (ESI-MS) 543 (M−1)

Compound 801 N-[3-(3-Fluoro-benzylidene-hydrazinocarbonyl)-benzo[b]thiophen-2-yl]-3-(4-hydroxymethyl-piperidin-1-ylmethyl)-benzamide

The title compound 801 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.40 (2H, m), 1.53 (1H, m), 1.72 (2H, m), 2.09 (2H, m), 2.96 (2H, m), 3.50 (2H, d, J=6.1 Hz), 3.66 (2H, s), 7.13 (1H, m), 7.31 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.35-7.66 (6H, m), 7.85 (2H, m), 7.94 (1H, d, J=7.8 Hz), 8.02 (1H, s), 8.23 (1H, s), 9.52 (1H, bs), 12.73 (1H, bs)

Mass spectrometric value (ESI-MS) 543 (M−1)

Compound 802 N-[3-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-benzo[b]thiophen-2-yl]-3-(4-hydroxymethyl-piperidin-1-ylmethyl)-benzamide

The title compound 802 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.40 (2H, m), 1.15 (1H, m), 1.72 (2H, m), 2.09 (2H, m), 2.95 (2H, m), 3.50 (2H, d, J=6.1 Hz), 3.65 (2H, s), 7.27 (1H, m), 7.40 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.47 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.55 (1H, d, J=8.0 Hz), 7.60 (1H, d, J=7.6 Hz), 7.82 (2H, m), 7.90 (1H, m), 7.95 (1H, d, J=8.0 Hz), 8.00 (1H, s), 8.06 (1H, s), 8.35 (1H, s), 9.69 (1H, bs), 12.63 (1H, bs)

Mass spectrometric value (ESI-MS) 627 (M−1)

Compound 803 3-(4-Hydroxymethyl-piperidin-1-ylmethyl)-N-[3-(4-methoxy-benzylidene-hydrazinocarbonyl)-benzo[b]thiophen-2-yl]-benzamide

The title compound 803 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCl₃, 400 MHz): δ 1.39 (2H, m), 1.52 (1H, m), 1.71 (2H, m), 2.07 (2H, m), 2.95 (2H, m), 3.49 (2H, d, J=6.1 Hz), 3.64 (2H, s), 3.83 (3H, s), 6.93 (2H, d, J=8.8 Hz), 7.29 (1H, m), 7.38-7.48 (2H, m), 7.60 (1H, d, J=7.6 Hz), 7.75 (1H, m), 7.84 (2H, dd, J=8.7 Hz, J=8.7 Hz), 7.95 (2H, m), 8.01 (1H, s), 8.20 (1H, s), 9.42 (1H, bs), 12.81 (1H, bs)

Mass spectrometric value (ESI-MS) 555 (M−1)

Example A

Compound 804 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[3-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-5,6-dihydro-4H-cyclopenta[b]thiophen-2-yl]-benzamide

Ethyl-2-aminocyclopenta(B)thiophene-3-carboxylate (compound A) (1.0 g) was dissolved in anhydrous methylene chloride (20.0 ml). Subsequently, pyridine (760 μl) and 3-(chloromethyl)benzoyl chloride (compound B) (880 μl) were added to the solution at 0° C., and the mixture was stirred at 0° C. for one hr. After the completion of the reaction, distilled water was added thereto, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated to give 2-(3-chloromethyl-benzoylamino)-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxylic acid ethyl ester as a useful intermediate (800 mg, crude yield 100%).

2-(3-Chloromethyl-benzoylamino)-5,6-dihydro-4H-cyclopenta[b]-thiophene-3-carboxylic acid ethyl ester (800 mg) produced by the above reaction was dissolved in anhydrous methylene chloride (10.0 ml). Triethylamine (420 μl) and diisopropanolamine (compound B′) (585 mg) were added to the solution at room temperature, and the mixture was stirred at room temperature for 15 hr. After the completion of the reaction, water was added thereto at room temperature, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated. The residue was purified by column chromatography eluted with a chloroform-methanol system to give 2-(3-{[bis-(2-hydroxy-propyl)-amino]-methyl}-benzoylamino)-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxylic acid ethyl ester as a useful intermediate (616 mg, yield 61%).

2-(3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-benzoylamino)-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxylic acid ethyl ester (616 mg) produced by the above reaction was dissolved in ethanol (10.0 ml). Hydrazine monohydrate (700 μl) was added to the solution, and the mixture was stirred at room temperature for 15 hr. After the completion of the reaction, water was added thereto at room temperature, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated. The residue was purified by column chromatography eluted with a chloroform-methanol system to give 3-{[bis-(2-hydroxy-propyl)-amino]-methyl}-N-(3-hydrazinocarbonyl-5,6-dihydro-4H-cyclopenta[b]thiophen-2-yl)-benzamide as a hydrazine compound (372 mg, yield 60%).

3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-(3-hydrazino-carbonyl-5,6-dihydro-4H-cyclopenta[b]thiophen-2-yl)benzamide (60.0 mg) produced by the above reaction was dissolved in anhydrous toluene (1.0 ml). 3,4-Dimethylbenzaldehyde (compound C) (70.0 μl) was added to the solution at room temperature, and the mixture was heated under reflux with stirring for 15 hr. After the completion of the reaction, water was added thereto at room temperature, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated. The residue was purified by column chromatography eluted with a chloroform-methanol system to give the title compound 804 (70.0 mg, yield 100%).

¹H-NMR (CDCl₃, 400 MHz): δ 1.13 (6H, m), 2.28 (6H, m), 2.46-2.66 (6H, m), 2.92 (2H, m), 3.05 (2H, m), 3.58-4.05 (4H, m), 7.12 (1H, m), 7.46 (3H, m), 7.64 (1H, d, J=5.1 Hz), 8.00 (2H, m), 8.22 (1H, m), 8.95 (1H, s), 13.16 (1H, m)

Mass spectrometric value (ESI-MS) 561 (M−1)

Compound 805 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[3-(4-methyl-benzylidene-hydrazinocarbonyl)-5,6-dihydro-4H-cyclopenta[b]-thiophen-2-yl]-benzamide

The title compound 805 was produced in substantially the same manner as in Example A.

¹H-NMR (CDCl₃, 400 MHz): δ 1.13 (6H, m), 2.36 (3H, m), 2.49 (4H, m), 2.62 (2H, m), 2.89 (2H, m), 3.02 (2H, m), 3.60-4.06 (4H, m), 7.13 (2H, m), 7.44 (2H, m), 7.67 (2H, dd, J=8.2 Hz, J=2.6 Hz), 8.01 (2H, m), 8.23 (1H, m), 8.97 (1H, s), 13.16 (1H, m)

Mass spectrometric value (ESI-MS) 547 (M−1)

Compound 806 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[3-(3-fluoro-benzylidene-hydrazinocarbonyl)-5,6-dihydro-4H-cyclopenta[b]thiophen-2-yl]-benzamide

The title compound 806 was produced in substantially the same manner as in Example A.

¹H-NMR (CDCl₃, 400 MHz): δ 1.14 (6H, m), 2.50 (4H, m), 2.65 (2H, m), 2.89 (2H, m), 3.03 (2H, m), 3.68-4.10 (4H, m), 7.02 (1H, m), 7.27 (1H, m), 7.45 (3H, m), 7.67 (1H, m), 8.03 (1H, m), 8.15 (1H, d, J=2.7 Hz), 8.29 (1H, d, J=10.0 Hz), 9.11 (1H, s), 13.17 (1H, m)

Mass spectrometric value (ESI-MS) 551 (M−1)

Compound 807 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[3-(4-fluoro-benzylidene-hydrazinocarbonyl)-5,6-dihydro-4H-cyclopenta[b]thiophen-2-yl]-benzamide

The title compound 807 was produced in substantially the same manner as in Example A.

¹H-NMR (CDCl₃, 400 MHz): δ 1.12 (6H, m), 2.49 (4H, m), 2.64 (2H, m), 2.88 (2H, m), 3.02 (2H, m), 3.02-4.06 (4H, m), 7.01 (2H, m), 7.45 (2H, m), 7.79 (2H, m), 8.02 (1H, m), 8.10 (1H, s), 8.27 (1H, d, J=5.9 Hz), 9.04 (1H, s), 13.18 (1H, m)

Mass spectrometric value (ESI-MS) 551 (M−1)

Compound 808 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[3-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-5,6-dihydro-4H-cyclopenta[b]thiophen-2-yl]-benzamide

The title compound 808 was produced in substantially the same manner as in Example A.

¹H-NMR (CDCl₃, 400 MHz): δ 1.12 (6H, m), 2.25-3.07 (10H, m), 3.58-4.10 (4H, m), 7.31 (1H, m), 7.46 (2H, m), 7.86 (1H, m), 7.98 (1H, s), 8.05 (1H, m), 8.33 (2H, m), 9.28 (1H, m), 13.18 (1H, m)

Mass spectrometric value (ESI-MS) 635 (M−1)

Compound 809 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[3-(4-methoxy-benzylidene-hydrazinocarbonyl)-5,6-dihydro-4H-cyclopenta[b]thiophen-2-yl]-benzamide

The title compound 809 was produced in substantially the same manner as in Example A.

¹H-NMR (CDCl₃, 400 MHz): δ 1.13 (6H, m), 2.35-2.65 (6H, m), 2.91 (2H, m), 3.04 (2H, m), 3.59-4.04 (7H, m), 6.88 (2H, d, J=8.8 Hz), 7.46 (2H, m), 7.76 (2H, dd, J=9.1 Hz, J=2.1 Hz), 8.02 (2H, m), 8.24 (1H, m), 8.92 (1H, s), 13.20 (1H, m)

Mass spectrometric value (ESI-MS) 563 (M−1)

Example B

Compound 810 3-[(2-Diethylamino-ethylamino)-methyl]-N-[3-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-5,6-dihydro-4H-cyclopenta[b]-thiophen-2-yl]-benzamide

Ethyl-2-aminocyclopenta(B)thiophene-3-carboxylate (compound A) (1.0 g) was dissolved in anhydrous methylene chloride (20.0 ml). Subsequently, pyridine (760 μl) and 3-(chloromethyl)benzoyl chloride (compound B) (880 μl) were added to the solution at 0° C., and the mixture was stirred at 0° C. for one hr. After the completion of the reaction, distilled water was added thereto, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated to give 2-(3-chloromethyl-benzoylamino)-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxylic acid ethyl ester as a useful intermediate (800 mg, crude yield 100%).

2-(3-Chloromethyl-benzoylamino)-5,6-dihydro-4H-cyclopenta[b]-thiophene-3-carboxylic acid ethyl ester (800 mg) produced by the above reaction was dissolved in anhydrous methylene chloride (10.0 ml). Triethylamine (420 μl) and N,N-diethylethylenediamine (compound B′) (510 mg) were added to the solution at room temperature, and the mixture was stirred at room temperature for 15 hr. After the completion of the reaction, water was added thereto at room temperature, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated. The residue was purified by column chromatography eluted with a chloroform-methanol system to give 2-{3-[(2-diethylamino-ethylamino)-methyl]-benzoylamino}-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxylic acid ethyl ester as a useful intermediate (671 mg, yield 68%).

2-{3-[(2-Diethylamino-ethylamino)-methyl]-benzoylamino}-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxylic acid ethyl ester (671 mg) produced by the above reaction was dissolved in ethanol (10.0 ml), hydrazine monohydrate (700 μl) was added to the solution, and the mixture was stirred at room temperature for 15 hr. After the completion of the reaction, water was added thereto at room temperature, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated. The residue was purified by column chromatography eluted with a chloroform-methanol system to give 3-[(2-diethylamino-ethylamino)-methyl-N-(3-hydrazinocarbonyl-5,6-dihydro-4H-cyclopenta[b]thiophen-2-yl)-benzamide (438 mg, yield 65%) as a hydrazine compound.

The hydrazine compound 3-[(2-diethylamino-ethylamino)-methyl-N-(3-hydrazinocarbonyl-5,6-dihydro-4H-cyclopenta[b]thiophen-2-yl)-benzamide (50 mg) produced by the above reaction was dissolved in anhydrous toluene (1.0 ml). 3,4-Dimethylbenzaldehyde (compound C) (70.0 μl) was added to the solution at room temperature, and the mixture was stirred at room temperature for 15 hr. After the completion of the reaction, the reaction product was purified by column chromatography eluted with a chloroform-methanol system to give the title compound 810 (43.0 mg, yield 66%).

¹H-NMR (CDCl₃, 400 MHz): δ 1.04 (6H, t, J=7.1 Hz), 2.28 (6H, s), 2.47-2.67 (8H, m), 2.74 (2H, m), 2.90 (2H, m), 3.05 (2H, m), 3.90 (2H, s), 7.14 (1H, d, J=7.8 Hz), 7.43 (2H, m), 7.57 (1H, d, J=7.8 Hz), 7.61 (1H, s), 7.94 (1H, d, J=7.8 Hz), 7.99 (2H, s), 8.96 (1H, bs), 12.95 (1H, bs)

Mass spectrometric value (ESI-MS) 544 (M−1)

Compound 811 3-[(2-Diethylamino-ethylamino)-methyl]-N-[3-(4-methyl-benzylidene-hydrazinocarbonyl)-5,6-dihydro-4H-cyclopenta[b]thiophen-2-yl]-benzamide

The title compound 811 was produced in substantially the same manner as in Example B.

¹H-NMR (CDCl₃, 400 MHz): δ 1.06 (6H, t, J=7.1 Hz), 2.38 (3H, s), 2.51-2.80 (10H, m), 2.93 (2H, m), 3.06 (2H, m), 3.91 (2H, s), 7.21 (2H, d, J=8.0 Hz), 7.45 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.58 (1H, d, J=7.6 Hz), 7.67 (2H, d, J=7.8 Hz), 7.95 (1H, d, J=7.8 Hz), 8.00 (1H, s), 8.04 (1H, s), 8.98 (1H, bs), 12.95 (1H, bs)

Mass spectrometric value (ESI-MS) 530 (M−1)

Compound 812 3-[(2-Diethylamino-ethylamino)-methyl]-N-[3-(3-fluoro-benzylidene-hydrazinocarbonyl)-5,6-dihydro-4H-cyclopenta[b]thiophen-2-yl]-benzamide

The title compound 812 was produced in substantially the same manner as in Example B.

¹H-NMR (CDCl₃, 400 MHz): δ 1.07 (6H, t, J=7.2 Hz), 2.51 (2H, m), 2.66 (4H, m), 2.73 (2H, m), 2.78 (2H, m), 2.89 (2H, m), 3.04 (2H, m), 3.90 (2H, s), 7.09 (1H, m), 7.35 (1H, m), 7.40-7.60 (4H, m), 7.92 (1H, d, J=7.8 Hz), 7.98 (1H, s), 8.09 (1H, s), 9.09 (1H, bs), 12.83 (1H, bs)

Mass spectrometric value (ESI-MS) 534 (M−1)

Compound 813 3-[(2-Diethylamino-ethylamino)-methyl]-N-[3-(4-fluoro-benzylidene-hydrazinocarbonyl)-5,6-dihydro-4H-cyclopenta[b]thiophen-2-yl]-benzamide

The title compound 813 was produced in substantially the same manner as in Example B.

¹H-NMR (CDCl₃, 400 MHz): δ 1.05 (6H, t, J=7.1 Hz), 2.49-2.70 (8H, m), 2.75 (2H, m), 2.91 (2H, t, J=7.3 Hz), 3.05 (2H, t, J=7.0 Hz), 3.90 (2H, s), 7.09 (2H, dd, J=8.6 Hz, J=8.6 Hz), 7.44 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.57 (1H, d, J=7.6 Hz), 7.76 (2H, m), 7.93 (1H, d, J=7.8 Hz), 7.99 (1H, s), 8.08 (1H, s), 9.02 (1H, bs), 12.88 (1H, bs)

Mass spectrometric value (ESI-MS) 534 (M−1)

Compound 814 N-[3-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-5,6-dihydro-4H-cyclopenta[b]thiophen-2-yl]-3-[(2-diethylamino-ethylamino)-methyl]-benzamide

The title compound 814 was produced in substantially the same manner as in Example B.

¹H-NMR (CDCl₃, 400 MHz): δ 1.03 (6H, t, J=7.2 Hz), 2.46-2.65 (8H, m), 2.71 (2H, m), 2.88 (2H, t, J=7.1 Hz), 3.03 (2H, t, J=6.8 Hz), 3.88 (2H, s), 7.45 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.54 (2H, m), 7.90 (2H, m), 7.98 (2H, m), 8.17 (1H, s), 9.13 (1H, bs), 12.78 (1H, bs)

Mass spectrometric value (ESI-MS) 618 (M−1)

Compound 815 3-[(2-Diethylamino-ethylamino)-methyl]-N-[3-(4-methoxy-benzylidene-hydrazinocarbonyl)-5,6-dihydro-4H-cyclopenta[b]thiophen-2-yl]-benzamide

The title compound 815 was produced in substantially the same manner as in Example B.

¹H-NMR (CDCl₃, 400 MHz): δ 1.03 (6H, t, J=7.1 Hz), 2.45-2.65 (8H, m), 2.71 (2H, m), 2.89 (2H, t, J=7.2 Hz), 3.03 (2H, t, J=7.1 Hz), 3.83 (3H, s), 3.89 (2H, s), 6.89 (2H, d, J=8.8 Hz), 7.44 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.56 (1H, d, J=7.6 Hz), 7.69 (2H, d, J=8.8 Hz), 7.93 (1H, d, J=8.1 Hz), 7.99 (2H, m), 8.93 (1H, bs), 12.94 (1H, bs)

Mass spectrometric value (ESI-MS) 546 (M−1)

Compound 816 N-[3-(3,4-Dimethyl-benzylidene-hydrazinocarbonyl)-5,6-dihydro-4H-cyclopenta[b]thiophen-2-yl]-3-(4-hydroxymethyl-piperidin-1-ylmethyl)-benzamide

The title compound 816 was produced in substantially the same manner as in Example A.

¹H-NMR (CDCl₃, 400 MHz): δ 1.38 (2H, m), 1.50 (1H, m), 1.73 (2H, d, J=12.0 Hz), 2.07 (2H, m), 2.30 (6H, s), 2.56 (2H, m), 2.94 (4H, m), 3.07 (2H, m), 3.50 (2H, d, J=6.1 Hz), 3.65 (2H, s), 7.17 (1H, d, J=7.8 Hz), 7.46 (2H, m), 7.60 (1H, d, J=7.8 Hz), 7.64 (1H, s), 7.97 (1H, d, J=7.6 Hz), 8.01 (2H, m), 8.96 (1H, s), 12.97 (1H, s)

Mass spectrometric value (ESI-MS) 543 (M−1)

Compound 817 3-(4-Hydroxymethyl-piperidin-1-ylmethyl)-N-[3-(4-methyl-benzylidene-hydrazinocarbonyl)-5,6-dihydro-4H-cyclopenta[b]thiophen-2-yl]-benzamide

The title compound 817 was produced in substantially the same manner as in Example A.

¹H-NMR (CDCl₃, 400 MHz): δ 1.39 (2H, m), 1.52 (1H, m), 1.72 (2H, d, J=11.5 Hz), 2.11 (2H, m), 2.39 (3H, s), 2.55 (2H, m), 2.90-3.02 (4H, m), 3.07 (2H, t, J=7.1 Hz), 3.49 (2H, d, J=6.1 Hz), 3.69 (2H, s), 7.21 (2H, d, J=8.1 Hz), 7.45 (1H, dd, J=7.5 Hz, J=7.5 Hz), 7.61 (1H, d, J=7.6 Hz), 7.67 (2H, d, J=8.0 Hz), 7.94-8.02 (2H, m), 8.05 (1H, s), 8.97 (1H, s), 12.95 (1H, s)

Mass spectrometric value (ESI-MS) 529 (M−1)

Compound 818 N-[3-(4-Fluoro-benzylidene-hydrazinocarbonyl)-5,6-dihydro-4H-cyclopenta[b]thiophen-2-yl]-3-(4-hydroxymethyl-piperidin-1-ylmethyl)-benzamide

The title compound 818 was produced in substantially the same manner as in Example A.

¹H-NMR (CDCl₃, 400 MHz): δ 1.35 (2H, m), 1.45-1.75 (3H, m), 2.03 (2H, m), 2.57 (2H, m), 2.94 (4H, m), 3.08 (2H, d, J=7.1 Hz), 3.50 (2H, d, J=6.1 Hz), 3.60 (2H, s), 7.12 (2H, dd, J=8.6 Hz, J=8.6 Hz), 7.45 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.58 (1H, d, J=7.6 Hz), 7.80 (2H, m), 7.95 (1H, d, J=7.8 Hz), 8.01 (1H, s), 8.09 (1H, s), 8.99 (1H, s), 12.90 (1H, s)

Mass spectrometric value (ESI-MS) 533 (M−1)

Compound 819 N-[3-(3-Fluoro-benzylidene-hydrazinocarbonyl)-5,6-dihydro-4H-cyclopenta[b]thiophen-2-yl]-3-(4-hydroxymethyl-piperidin-1-ylmethyl)-benzamide

The title compound 819 was produced in substantially the same manner as in Example A.

¹H-NMR (CDCl₃, 400 MHz): δ 1.36-1.62 (3H, m), 1.74 (2H, m), 2.14 (2H, m), 2.56 (2H, m), 2.90-3.14 (6H, m), 3.50 (2H, d, J=6.1 Hz), 3.72 (2H, s), 7.11 (1H, m), 7.38 (1H, m), 7.44-7.59 (3H, m), 7.62 (1H, m), 7.90-8.03 (2H, m), 8.10 (1H, s), 9.06 (1H, s), 12.88 (1H, s)

Mass spectrometric value (ESI-MS) 533 (M−1)

Compound 820 N-[3-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-5,6-dihydro-4H-cyclopenta[b]thiophen-2-yl]-3-(4-hydroxymethyl-piperidin-1-ylmethyl)-benzamide

The title compound 820 was produced in substantially the same manner as in Example A.

¹H-NMR (CDCl₃, 400 MHz): δ 1.30-1.77 (5H, m), 2.03 (2H, m), 2.58 (2H, m), 2.93 (4H, m), 3.08 (2H, d, J=7.1 Hz), 3.50 (2H, d, J=6.3 Hz), 3.60 (2H, s), 7.46 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.58 (2H, m), 7.90-8.06 (4H, m), 8.19 (1H, s), 9.09 (1H, s), 12.81 (1H, s)

Mass spectrometric value (ESI-MS) 617 (M−1)

Compound 821 3-(4-Hydroxymethyl-piperidin-1-ylmethyl)-N-[3-(4-methoxy-benzylidene-hydrazinocarbonyl)-5,6-dihydro-4H-cyclopenta[b]thiophen-2-yl]-benzamide

The title compound 821 was produced in substantially the same manner as in Example A.

¹H-NMR (CDCl₃, 400 MHz): δ 1.34 (2H, m), 1.50 (1H, m), 1.70 (2H, m), 2.02 (2H, m), 2.54 (2H, m), 2.91 (4H, m), 3.59 (2H, m), 3.49 (2H, d, J=6.3 Hz), 3.58 (2H, s), 3.85 (3H, s), 6.92 (2H, m), 7.44 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.57 (1H, d, J=7.6 Hz), 7.72 (2H, m), 7.94 (1H, d, J=7.8 Hz), 8.01 (2H, m), 8.92 (1H, s), 12.96 (1H, s)

Mass spectrometric value (ESI-MS) 545 (M−1)

Compound 822 3-Dimethylaminomethyl-N-[3-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-benzamide

The title compound 822 was produced in substantially the same manner as in Example A.

¹H-NMR (CDCl₃, 400 MHz): δ 2.26 (6H, s), 2.29 (6H, s), 2.58 (3H, s), 3.53 (2H, s), 6.51 (1H, d, J=1.0 Hz), 7.17 (1H, d, J=7.8 Hz), 7.46 (2H, m), 7.57 (1H, d, J=7.6 Hz), 7.64 (1H, s), 7.95 (2H, m), 8.08 (1H, s), 9.11 (1H, s), 12.93 (1H, bs)

Mass spectrometric value (ESI-MS) 447 (M−1)

Compound 823 3-Dimethylaminomethyl-N-[4-methyl-3-(4-methyl-benzylidene-hydrazinocarbonyl)-thiophen-2-yl]-benzamide

The title compound 823 was produced in substantially the same manner as in Example A.

¹H-NMR (CDCl₃, 400 MHz): δ 2.26 (6H, s), 2.39 (3H, s), 2.58 (3H, s), 3.53 (2H, s), 6.52 (1H, d, J=1.0 Hz), 7.23 (2H, d, J=7.8 Hz), 7.46 (1H, dd, J=8.3 Hz, J=8.3 Hz), 7.57 (1H, d, J=7.8 Hz), 7.69 (2H, d, J=7.6 Hz), 7.95 (2H, m), 8.12 (1H, s), 9.12 (1H, s), 12.91 (1H, bs)

Mass spectrometric value (ESI-MS) 433 (M−1)

Compound 824 N-[3-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-3-dimethylaminomethyl-benzamide

The title compound 824 was produced in substantially the same manner as in Example A.

¹H-NMR (CDCl₃, 400 MHz): δ 2.26 (6H, s), 2.52 (3H, s), 3.53 (2H, s), 6.49 (1H, s), 7.47 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.57 (2H, m), 7.94 (3H, m), 8.04 (1H, m), 8.27 (1H, s), 9.36 (1H, bs), 12.66 (1H, bs)

Mass spectrometric value (ESI-MS) 521 (M−1)

Compound 825 3-Dimethylaminomethyl-N-[3-(4-methoxy-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-benzamide

The title compound 825 was produced in substantially the same manner as in Example A.

¹H-NMR (CDCl₃, 400 MHz): δ 2.26 (6H, s), 2.57 (3H, s), 3.53 (2H, s), 3.85 (3H, s), 6.51 (1H, d, J=1.0 Hz), 6.93 (2H, m), 7.46 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.57 (1H, d, J=7.8 Hz), 7.74 (2H, d, J=8.8 Hz), 7.95 (2H, m), 8.09 (1H, s), 9.09 (1H, s), 12.93 (1H, bs)

Mass spectrometric value (ESI-MS) 449 (M−1)

Compound 826 N-[3-(3,4-Dimethyl-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-3-(4-pyrimidin-2-yl-piperazin-1-ylmethyl)-benzamide

The title compound 826 was produced in substantially the same manner as in Example A.

¹H-NMR (CDCl₃, 400 MHz): δ 2.29 (6H, s), 2.53 (4H, t, J=5.0 Hz), 2.59 (3H, s), 3.63 (2H, s), 3.84 (4H, t, J=5.0 Hz), 6.45 (1H, dd, J=4.6 Hz, J=4.6 Hz), 6.54 (1H, s), 7.17 (1H, d, J=7.6 Hz), 7.47 (2H, m), 7.60 (1H, d, J=7.6 Hz), 7.64 (1H, s), 7.96 (1H, d, J=7.8 Hz), 8.05 (1H, s), 8.07 (1H, s), 8.28 (2H, d, J=4.6 Hz), 9.07 (1H, s), 12.99 (1H, bs)

Mass spectrometric value (ESI-MS) 566 (M−1)

Compound 827 N-[4-Methyl-3-(4-methyl-benzylidene-hydrazinocarbonyl)-thiophen-2-yl]-3-(4-pyrimidin-2-yl-piperazin-1-ylmethyl)-benzamide

The title compound 827 was produced in substantially the same manner as in Example A.

¹H-NMR (CDCl₃, 400 MHz): δ 2.39 (3H, s), 2.53 (4H, t, J=5.0 Hz), 2.59 (3H, s), 3.64 (2H, s), 3.85 (4H, t, J=4.7 Hz), 6.46 (1H, dd, J=4.7 Hz, J=4.7 Hz), 6.53 (1H, s), 7.21 (2H, d, J=8.0 Hz), 7.47 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.60 (1H, d, J=7.6 Hz), 7.68 (2H, d, J=8.1 Hz), 7.96 (1H, d, J=7.8 Hz), 8.05 (1H, s), 8.11 (1H, s), 8.29 (2H, d, J=4.6 Hz), 9.09 (1H, s), 12.97 (1H, bs)

Mass spectrometric value (ESI-MS) 552 (M−1)

Compound 828 N-[3-(4-Fluoro-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-3-(4-pyrimidin-2-yl-piperazin-1-ylmethyl)-benzamide

The title compound 828 was produced in substantially the same manner as in Example A.

¹H-NMR (CDCl₃, 400 MHz): δ 2.54 (4H, t, J=5.0 Hz), 2.59 (3H, s), 3.64 (2H, s), 3.85 (4H, t, J=5.1 Hz), 6.46 (1H, dd, J=4.9 Hz, J=4.9 Hz), 6.54 (1H, s), 7.10 (2H, m), 7.46 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.60 (1H, d, J=7.6 Hz), 7.79 (2H, m), 7.95 (1H, d, J=7.8 Hz), 8.05 (1H, s), 8.15 (1H, s), 8.29 (2H, d, J=4.9 Hz), 9.12 (1H, s), 12.92 (1H, bs)

Mass spectrometric value (ESI-MS) 556 (M−1)

Compound 829 N-[3-(3-Fluoro-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-3-(4-pyrimidin-2-yl-piperazin-1-ylmethyl)-benzamide

The title compound 829 was produced in substantially the same manner as in Example A.

¹H-NMR (CDCl₃, 400 MHz): δ 2.53 (4H, t, J=5.0 Hz), 2.59 (3H, s), 3.64 (2H, s), 3.85 (4H, t, J=5.0 Hz), 6.46 (1H, dd, J=4.7 Hz, J=4.7 Hz), 6.55 (1H, s), 7.12 (1H, m), 7.38 (1H, m), 7.46-7.64 (4H, m), 7.95 (1H, m), 8.05 (1H, m), 8.17 (1H, s), 8.28 (2H, d, J=4.6 Hz), 9.17 (1H, s), 12.87 (1H, bs)

Mass spectrometric value (ESI-MS) 556 (M−1)

Compound 830 N-[3-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-3-(4-pyrimidin-2-yl-piperazin-1-ylmethyl)-benzamide

The title compound 830 was produced in substantially the same manner as in Example A.

¹H-NMR (CDCl₃, 400 MHz): δ 2.53 (4H, t, J=5.0 Hz), 2.59 (3H, s), 3.65 (2H, s), 3.85 (4H, t, J=5.0 Hz), 6.46 (1H, dd, J=4.8 Hz, J=4.8 Hz), 6.55 (1H, s), 7.49 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.55 (1H, d, J=8.3 Hz), 7.61 (1H, d, J=7.6 Hz), 7.96 (2H, m), 8.05 (2H, m), 8.26 (1H, s), 8.28 (2H, d, J=4.6 Hz), 9.21 (1H, s), 12.84 (1H, bs)

Mass spectrometric value (ESI-MS) 640 (M−1)

Compound 831 N-[3-(4-Methoxy-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-3-(4-pyrimidin-2-yl-piperazin-1-ylmethyl)-benzamide

The title compound 831 was produced in substantially the same manner as in Example A.

¹H-NMR (CDCl₃, 400 MHz): δ 2.53 (4H, t, J=4.8 Hz), 2.60 (3H, s), 3.64 (2H, s), 3.84 (7H, m), 6.45 (1H, d, J=4.8 Hz), 6.55 (1H, s), 6.93 (2H, d, J=8.8 Hz), 7.47 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.61 (1H, d, J=7.6 Hz), 7.74 (2H, d, J=8.8 Hz), 7.97 (1H, d, J=7.8 Hz), 8.05 (1H, s), 8.08 (1H, s), 8.29 (2H, d, J=4.4 Hz), 9.02 (1H, s), 13.04 (1H, bs)

Mass spectrometric value (ESI-MS) 568 (M−1)

Compound 832 N-[3-(3,4-Dimethyl-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-3-(1,4-dioxa-8-aza-spiro[4,5]dec-8-ylmethyl)-benzamide

The title compound 832 was produced in substantially the same manner as in Example A.

¹H-NMR (CDCl₃, 400 MHz): δ 1.76 (4H, m), 2.31 (6H, s), 2.55 (4H, m), 2.62 (3H, s), 3.62 (2H, s), 3.94 (4H, s), 6.55 (1H, s), 7.26 (1H, m), 7.47 (2H, m), 7.53 (1H, m), 7.66 (1H, s), 7.95 (1H, d, J=7.8 Hz), 8.01 (1H, s), 8.07 (1H, s), 9.03 (1H, s), 13.03 (1H, bs)

Mass spectrometric value (ESI-MS) 545 (M−1)

Compound 833 3-(1,4-Dioxa-8-aza-spiro[4,5]dec-8-yl methyl]-N-[4-methyl-3-(4-methyl-benzylidene-hydrazinocarbonyl)-thiophen-2-yl]-benzamide

The title compound 833 was produced in substantially the same manner as in Example A.

¹H-NMR (CDCl₃, 400 MHz): δ 1.76 (4H, t, J=5.5 Hz), 2.40 (3H, s), 2.55 (4H, m), 2.60 (3H, s), 3.62 (2H, s), 3.94 (4H, s), 6.54 (1H, s), 7.23 (2H, d, J=8.0 Hz), 7.45 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.58 (1H, d, J=7.8 Hz), 7.70 (2H, d, J=8.0 Hz), 7.93 (1H, d, J=7.8 Hz), 8.01 (1H, s), 8.11 (1H, s), 9.06 (1H, s), 12.97 (1H, bs)

Mass spectrometric value (ESI-MS) 531 (M−1)

Compound 834 3-(1,4-Dioxa-8-aza-spiro[4,5]dec-8-ylmethyl]-N-[3-(4-fluoro-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-benzamide

The title compound 834 was produced in substantially the same manner as in Example A.

¹H-NMR (CDCl₃, 400 MHz): δ 1.76 (4H, t, J=5.4 Hz), 2.56 (4H, m), 2.59 (3H, s), 3.62 (2H, s), 3.94 (4H, s), 6.55 (1H, s), 7.12 (2H, dd, J=8.6 Hz, J=8.6 Hz), 7.45 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.58 (1H, d, J=7.8 Hz), 7.81 (2H, m), 7.93 (1H, d, J=7.6 Hz), 8.01 (1H, s), 8.15 (1H, s), 9.10 (1H, s), 12.91 (1H, bs)

Mass spectrometric value (ESI-MS) 535 (M−1)

Compound 835 3-(1,4-Dioxa-8-aza-spiro[4,5]dec-8-ylmethyl]-N-[3-(3-fluoro-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-benzamide

The title compound 835 was produced in substantially the same manner as in Example A.

¹H-NMR (CDCl₃, 400 MHz): δ 1.76 (4H, t, J=5.4 Hz), 2.55 (7H, m), 3.62 (2H, s), 3.94 (4H, s), 6.51 (1H, s), 7.11 (1H, m), 7.34-7.60 (5H, m), 7.91 (1H, d, J=7.6 Hz), 8.01 (1H, s), 8.18 (1H, s), 9.22 (1H, s), 12.78 (1H, bs)

Mass spectrometric value (ESI-MS) 535 (M−1)

Compound 836 N-[3-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-3-(1,4-dioxa-8-aza-spiro[4,5]dec-8-ylmethyl]-benzamide

The title compound 836 was produced in substantially the same manner as in Example A.

¹H-NMR (CDCl₃, 400 MHz): δ 1.76 (4H, t, J=5.5 Hz), 2.57 (7H, m), 3.62 (2H, s), 3.94 (4H, s), 6.53 (1H, d, J=1.0 Hz), 7.46 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.57 (2H, m), 7.91 (1H, m), 7.96-8.02 (2H, m), 8.05 (1H, d, J=1.7 Hz), 8.27 (1H, s), 9.25 (1H, s), 12.76 (1H, bs)

Mass spectrometric value (ESI-MS) 619 (M−1)

Compound 837 3-(1,4-Dioxa-8-aza-spiro[4,5]dec-8-ylmethyl]-N-[3-(4-methoxy-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-benzamide

The title compound 837 was produced in substantially the same manner as in Example A.

¹H-NMR (CDCl₃, 400 MHz): δ 1.76 (4H, m), 2.56 (4H, m), 2.61 (3H, s), 3.63 (2H, s), 3.86 (3H, s), 3.94 (4H, s), 6.55 (1H, s), 6.95 (2H, m), 7.46 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.58 (1H, m), 7.76 (2H, d, J=8.5 Hz), 7.95 (1H, d, J=7.6 Hz), 8.01 (1H, s), 8.08 (1H, s), 9.00 (1H, s), 13.03 (1H, bs)

Mass spectrometric value (ESI-MS) 547 (M−1)

Compound 838 3-{[Bis-(2-diethylamino-ethyl)-amino]-methyl}-N-[3-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-benzamide

The title compound 838 was produced in substantially the same manner as in Example B.

¹H-NMR (CDCl₃, 400 MHz): δ 0.98 (12H, t, J=7.1 Hz), 2.29 (6H, m), 2.43-2.66 (19H, m), 3.73 (2H, s), 6.52 (1H, d, J=1.0 Hz), 7.17 (1H, d, J=7.8 Hz), 7.44 (2H, m), 7.62 (2H, m), 7.92 (1H, d, J=7.8 Hz), 8.01 (1H, s), 8.09 (1H, s)

Mass spectrometric value (ESI-MS) 617 (M−1)

Compound 839 3-{[Bis-(2-diethylamino-ethyl)-amino]-methyl}-N-[4-methyl-3-(4-methyl-benzylidene-hydrazinocarbonyl)-thiophen-2-yl]-benzamide

The title compound 839 was produced in substantially the same manner as in Example B.

¹H-NMR (CDCl₃, 400 MHz): δ 0.98 (12H, t, J=7.1 Hz), 2.38 (3H, s), 2.45-2.65 (19H, m), 3.72 (2H, s), 6.51 (1H, d, J=1.2 Hz), 7.22 (2H, d, J=7.8 Hz), 7.43 (1H, m), 7.60 (1H, m), 7.68 (2H, d, J=7.8 Hz), 7.91 (1H, d, J=7.8 Hz), 8.00 (1H, s), 8.13 (1H, s)

Mass spectrometric value (ESI-MS) 603 (M−1)

Compound 840 3-{[Bis-(2-diethylamino-ethyl)-amino]-methyl}-N-[3-(4-fluoro-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-benzamide

The title compound 840 was produced in substantially the same manner as in Example B.

¹H-NMR (CDCl₃, 400 MHz): δ 0.98 (12H, t, J=7.1 Hz), 2.43-2.66 (19H, m), 3.72 (2H, s), 6.50 (1H, d, J=1.0 Hz), 7.10 (2H, dd, J=8.5 Hz, J=8.5 Hz), 7.44 (1H, m), 7.62 (1H, d, J=7.6 Hz), 7.79 (2H, m), 7.89 (1H, d, J=7.8 Hz), 8.00 (1H, s), 8.18 (1H, s)

Mass spectrometric value (ESI-MS) 607 (M−1)

Compound 841 3-{[Bis-(2-diethylamino-ethyl)-amino]-methyl}-N-[3-(3-fluoro-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-benzamide

The title compound 841 was produced in substantially the same manner as in Example B.

¹H-NMR (CDCl₃, 400 MHz): δ 0.98 (12H, t, J=7.1 Hz), 2.44-2.64 (19H, m), 3.73 (2H, s), 6.51 (1H, s), 7.11 (1H, s), 7.34-7.64 (5H, m), 7.90 (1H, d, J=7.8 Hz), 8.01 (1H, s), 8.19 (1H, s)

Mass spectrometric value (ESI-MS) 607 (M−1)

Compound 842 3-{[Bis-(2-diethylamino-ethyl)-amino]-methyl}-N-[3-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-benzamide

The title compound 842 was produced in substantially the same manner as in Example B.

¹H-NMR (CDCl₃, 400 MHz): δ 0.97 (12H, m), 2.42-2.64 (19H, m), 3.72 (2H, m), 6.47 (1H, d, J=1.0 Hz), 7.30-7.68 (4H, m), 7.77-8.05 (3H, m), 8.27 (1H, s)

Mass spectrometric value (ESI-MS) 691 (M−1)

Compound 843 3-{[Bis-(2-diethylamino-ethyl)-amino]-methyl}-N-[3-(4-methoxy-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-benzamide

The title compound 843 was produced in substantially the same manner as in Example B.

¹H-NMR (CDCl₃, 400 MHz): δ 0.98 (12H, t, J=7.2 Hz), 2.45-2.66 (19H, m), 3.72 (2H, s), 3.85 (3H, s), 6.52 (1H, d, J=1.0 Hz), 6.93 (2H, d, J=8.8 Hz), 7.44 (1H, m), 7.62 (1H, d, J=7.8 Hz), 7.74 (2H, d, J=8.6 Hz), 7.92 (1H, d, J=7.8 Hz), 8.01 (1H, s), 8.10 (1H, s)

Mass spectrometric value (ESI-MS) 619 (M−1)

Compound 844 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[3-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-4,5-dimethyl-thiophen-2-yl]-benzamide

The title compound 844 was produced in substantially the same manner as in Example B.

¹H-NMR (CDCl₃, 400 MHz): δ 1.12 (6H, m), 2.26-2.64 (16H, m), 3.62-4.05 (4H, m), 7.13 (1H, m), 7.40-7.56 (3H, m), 7.65 (1H, m), 7.99 (1H, m), 8.04 (1H, s), 8.19 (1H, s), 9.10 (1H, s), 13.02 (1H, bs)

Mass spectrometric value (ESI-MS) 549 (M−1)

Compound 845 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[4,5-dimethyl-3-(4-methyl-benzylidene-hydrazinocarbonyl)-thiophen-2-yl]-benzamide

The title compound 845 was produced in substantially the same manner as in Example B.

¹H-NMR (CDCl₃, 400 MHz): δ 1.11 (6H, m), 2.28-2.64 (13H, m), 3.60-4.04 (4H, m), 7.21 (2H, m), 7.43 (2H, m), 7.73 (2H, m), 7.99 (1H, m), 8.07 (1H, s), 8.21 (1H, s), 9.09 (1H, bs), 13.01 (1H, bs)

Mass spectrometric value (ESI-MS) 535 (M−1)

Compound 846 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[3-(4-fluoro-benzylidene-hydrazinocarbonyl)-4,5-dimethyl-thiophen-2-yl]-benzamide

The title compound 846 was produced in substantially the same manner as in Example B.

¹H-NMR (CDCl₃, 400 MHz): δ 1.11 (6H, m), 2.24-2.52 (8H, m), 2.63 (2H, m), 3.60-4.06 (4H, m), 7.04 (2H, m), 7.43 (2H, m), 7.83 (2H, m), 7.99 (1H, m), 8.13 (1H, s), 8.24 (1H, m), 9.24 (1H, s), 12.98 (1H, bs)

Mass spectrometric value (ESI-MS) 539 (M−1)

Compound 847 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[3-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4,5-dimethyl-thiophen-2-yl]-benzamide

The title compound 847 was produced in substantially the same manner as in Example B.

¹H-NMR (CDCl₃, 400 MHz): δ 1.11 (6H, m), 2.19 (3H, m), 2.28 (3H, m), 2.52 (2H, m), 2.67 (2H, m), 3.60-4.10 (4H, m), 7.33 (1H, d, J=8.3 Hz), 7.38-7.50 (2H, m), 7.86 (1H, m), 7.98-8.10 (2H, m), 8.28 (1H, s), 8.36 (1H, s), 9.57 (1H, s), 13.03 (1H, s)

Mass spectrometric value (ESI-MS) 623 (M−1)

Compound 848 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[3-(4-methoxy-benzylidene-hydrazinocarbonyl)-4,5-dimethyl-thiophen-2-yl]-benzamide

The title compound 848 was produced in substantially the same manner as in Example B.

¹H-NMR (CDCl₃, 400 MHz): δ 1.11 (6H, m), 2.24-2.64 (10H, m), 3.60-4.04 (7H, m), 6.91 (2H, m), 7.43 (2H, m), 7.79 (2H, m), 8.02 (2H, m), 8.23 (1H, s), 9.04 (1H, s), 13.02 (1H, bs)

Mass spectrometric value (ESI-MS) 551 (M−1)

Compound 849 3-{[Bis-(2-diethylamino-ethyl)-amino]-methyl}-N-[3-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl]-benzamide

The title compound 849 was produced in substantially the same manner as in Example B.

¹H-NMR (CDCl₃, 400 MHz): δ 0.98 (12H, t, J=7.1 Hz), 1.91 (4H, m), 2.48 (8H, m), 2.58 (8H, m), 2.76 (2H, m), 2.87 (2H, m), 3.73 (2H, s), 7.44 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.57 (1H, d, J=8.3 Hz), 7.62 (1H, d, J=7.6 Hz), 7.90 (1H, d, J=8.1 Hz), 7.97 (1H, dd, J=8.3 Hz, J=2.0 Hz), 8.00 (1H, s), 8.04 (1H, d, J=1.7 Hz), 8.22 (1H, s)

Mass spectrometric value (ESI-MS) 731 (M−1)

Compound 850 3-{[Bis-(2-diethylamino-ethyl)-amino]-methyl}-N-[3-(4-methoxy-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo[b]-thiophen-2-yl]-benzamide

The title compound 850 was produced in substantially the same manner as in Example B.

¹H-NMR (CDCl₃, 400 MHz): δ 0.98 (12H, t, J=7.2 Hz), 1.92 (4H, m), 2.49 (8H, m), 2.58 (8H, m), 2.76 (2H, m), 2.89 (2H, m), 3.72 (2H, s), 3.88 (3H, s), 6.97 (2H, m), 7.27-7.46 (3H, m), 7.61 (1H, d, J=7.8 Hz), 7.92 (1H, d, J=7.3 Hz), 8.00 (1H, s), 8.10 (1H, s)

Mass spectrometric value (ESI-MS) 659 (M−1)

Example C

Compound 851 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[3-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-benzamide; hydrochloride

Diethyl ether (200 μl) was added to compound 591: 3-{[bis-(2-hydroxy-propyl)-amino]-methyl}-N-[3-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-benzamide (30 mg) produced by the process described in Example 8 at room temperature. Further, a few drops of 10% hydrochloric acid-methanol were added thereto, and the mixture was stirred for a few minunites. The reaction solution was then filtered through Kiriyama Rohto, and the crystals were washed with diethyl ether to give the title compound 851 (25 mg, yield 80%).

¹H-NMR (CDCl₃, 400 MHz): δ 1.14-1.27 (6H, m), 2.56 (3H, s), 2.90 (4H, m), 4.22 (4H, m), 6.53 (1H, m), 7.53 (2H, m), 7.70 (1H, m), 7.95 (1H, m), 8.03 (1H, d, J=8.0 Hz), 8.07 (1H, s), 8.20 (1H, d, J=7.3 Hz), 8.36 (1H, m)

Mass spectrometric value (ESI-MS) 609 (M−1)

Compound 852 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[3-(4-methoxy-benzylidene-hydrazinocarbonyl)-4-methyl-thiophen-2-yl]-benzamide; hydrochloride

The title compound 852 was produced in substantially the same manner as in Example C.

¹H-NMR (CD₃OD, 400 MHz): δ 1.22 (6H, d, J=6.1 Hz), 2.53 (3H, s), 3.30 (4H, m), 3.85 (3H, s), 4.20 (4H, m), 6.73 (1H, d, J=1.0 Hz), 6.99 (2H, d, J=8.5 Hz), 7.60-7.85 (4H, m), 8.00-8.29 (3H, m)

Mass spectrometric value (ESI-MS) 538 (M−1)

Example D

Compound 853 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-fluoro-phenyl]-benzamide; hydrochloride

Diethyl ether (200 μl) was added to compound 857: 3-{[bis-(2-hydroxy-propyl)-amino]-methyl}-N-[2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-fluoro-phenyl]-benzamide (30 mg) produced by the process described in Example A at room temperature, a few drops of 10% hydrochloric acid-methanol were further added thereto, and the mixture was stirred for a few minutes. The reaction solution was then filtered through Kiriyama Rohto, and the crystals were washed with diethyl ether to give the title compound 853 (25 mg, yield 80%).

¹H-NMR (CD₃OD, 400 MHz): δ 1.15-1.32 (6H, m), 3.00-3.40 (4H₃ m), 4.10-4.86 (4H, m), 7.44 (1H, m), 7.68-7.85 (4H, m), 8.03 (1H, d, J=7.8 Hz), 8.14 (2H, m), 8.36 (1H, m), 8.41 (1H, s), 8.62 (1H, m)

Mass spectrometric value (ESI-MS) 608 (M−1)

Compound 854 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[4-fluoro-2-(4-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide; hydrochloride

The title compound 854 was produced in substantially the same manner as in Example D.

¹H-NMR (CD₃OD, 400 MHz): δ 1.18 (6H, m), 3.30 (4H, m), 3.85 (3H, s), 4.00-4.30 (4H, m), 6.98 (2H, d, J=8.5 Hz), 7.35 (1H, m), 7.65-7.83-(5H, m), 8.00-8.17 (2H, m), 8.31 (1H, s), 8.70 (1H, m)

Mass spectrometric value (ESI-MS) 536 (M−1)

Example E

Compound 855 3-{[Bis-(2-diethylamino-ethyl)-amino]-methyl}-N-[3-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl]-benzamide; hydrochloride

Diethyl ether (200 μl) was added to compound 849: 3-{[bis-(2-diethylamino-ethyl)-amino]-methyl}-N-[3-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl]-benzamide (30 mg) produced by the process described in Example B at room temperature, a few drops of 10% hydrochloric acid-methanol were further added thereto, and the mixture was stirred for a few minutes. The reaction solution was then filtered through Kiriyama Rohto, and the crystals were washed with diethyl ether to give the title compound 855 (25 mg, yield 80%).

¹H-NMR (CD₃OD, 400 MHz): δ 1.28 (12H, m), 1.91 (4H, m), 2.77 (2H, m), 2.87 (2H, m), 3.04 (4H, m), 3.18 (8H, m), 3.40 (4H, m), 3.92 (2H, s), 7.62 (1H, m), 7.70 (1H, m), 7.77 (1H, m), 7.95 (1H, m), 8.01 (2H, m), 8.32 (2H, m)

Mass spectrometric value (ESI-MS) 732 (M−1)

Compound 856 3-{[Bis-(2-diethylamino-ethyl)-amino]-methyl}-N-[3-(4-methoxy-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl]-benzamide; hydrochloride

The title compound 856 was produced in substantially the same manner as in Example E.

¹H-NMR (CD₃OD, 400 MHz): δ 1.29 (12H, m), 1.89 (4H, m), 2.70-2.92 (4H, m), 3.00-3.28 (12H, m), 3.43 (4H, m), 3.87 (3H, s), 3.97 (2H, s), 7.20 (1H, m), 7.30-7.40 (2H, m), 7.52 (1H, m), 7.63 (1H, m), 7.77 (1H, m), 7.98 (1H, m), 8.04 (1H, s), 8.27 (1H, s)

Mass spectrometric value (ESI-MS) 660 (M−1)

Compound 857 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-fluoro-phenyl]-benzamide

The title compound 857 was produced in substantially the same manner as in Example A.

¹H-NMR (CD₃OD, 400 MHz): δ 1.08 (6H, m), 2.43-2.60 (4H, m), 3.60-3.95 (4H, m), 7.40 (1H, m), 7.50 (1H, m), 7.60 (1H, m), 7.69 (2H, d, J=7.6 Hz), 7.85 (1H, m), 8.07 (2H, m), 8.34 (1H, m), 8.38 (1H, s), 8.65 (1H, m),

Mass spectrometric value (ESI-MS) 608 (M−1)

Example F

Compound 858 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-4-piperidin-1-ylphenyl]-benzamide

5-Chloro-2-nitro-benzoic acid (compound A′) (5.0 g) was dissolved in methanol (150 ml). Thionyl chloride (9.5 ml) was added to the solution at 0° C., and the mixture was heated under reflux with stirring for 15 hr. After the completion of the reaction, distilled water was added thereto at 0° C., and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with distilled water and saturated brine, was dried over sodium sulfate, and was then concentrated to give 5-chloro-2-nitro-benzoic acid methyl ester as a useful intermediate (12.9 g, yield 92%).

5-Chloro-2-nitro-benzoic acid methyl ester (2.2 g) produced by the above reaction was dissolved in N,N-dimethylformamide (20 ml). Piperidine (compound D) (1.5 g) and potassium carbonate (1.5 g) were added to the solution at room temperature, and the mixture was stirred at 75° C. for 15 hr. After the completion of the reaction, distilled water was added thereto at room temperature, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with distilled water and saturated brine, was dried over sodium sulfate, and was then concentrated to give 2-nitro-5-piperidin-1-yl-benzoic acid methyl ester as a useful intermediate (1.86 g, crude yield 69%).

2-Nitro-5-piperidin-1-yl-benzoic acid methyl ester (4.8 g) produced by the above reaction was dissolved in ethanol (5.0 ml), and 10% palladium-carbon (500 mg) was added to the solution. The air in the reaction system was then replaced by hydrogen, and the reaction solution was stirred at room temperature for 15 hr. After the completion of the reaction, the atmosphere in the reaction system was replaced by nitrogen, followed by filtration through Celite. The filterate was concentrated, and the residue was purified by column chromatography using a hexane-acetone system to give 2-amino-5-piperidin-1-yl-benzoic acid methyl ester (compound A) as a useful intermediate (3.7 g, yield 87%).

2-Amino-5-piperidin-1-yl-benzoic acid methyl ester (compound A) (2.1 g) produced by the above reaction was dissolved in anhydrous methylene chloride (20.0 ml). Subsequently, pyridine (900 μl) and 3-(chloromethyl)benzoyl chloride (compound B) (740 μl) were added to the solution at 0° C., and the mixture was stirred at 0° C. for one hr. After the completion of the reaction, distilled water was added thereto, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate and was then concentrated. The residue was purified by column chromatography using a chloroform-acetone system to give 2-(3-chloromethyl-benzoylamino)-5-piperidin-1-yl-benzoic acid methyl ester as a useful intermediate (1.8 g, yield 50%).

2-(3-Chloromethyl-benzoylamino)-5-piperidin-1-yl-benzoic acid methyl ester (500 mg) produced by the above reaction was dissolved in anhydrous methylene chloride (5.0 ml). Triethylamine (400 μl) and N,N-diethyl-N′-methylethylenediamine (compound B′) (325 mg) were added to the solution at room temperature, and the mixture was stirred at room temperature for 15 hr. After the completion of the reaction, water was added thereto at room temperature, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated. The residue was purified by column chromatography eluted with a chloroform-methanol system to give 2-(3-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-benzoylamino)-5-piperidin-1-yl-benzoic acid methyl ester as a useful intermediate (612 mg, yield 98%).

2-(3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-benzoylamino)-5-piperidin-1-yl-benzoic acid methyl ester (612 mg) produced by the above reaction was dissolved in ethanol (10.0 ml). Hydrazine monohydrate (700 μl) was added to the solution, and the mixture was stirred at room temperature for 15 hr. After the completion of the reaction, water was added thereto at room temperature, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated. The residue was purified by column chromatography eluted with a chloroform-methanol system to give 3-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-N-(2-hydrazinocarbonyl-4-piperidin-1-yl-phenyl)-benzamide as a hydrazine compound (612 mg, yield 100%).

3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-(2-hydrazinocarbonyl-4-piperidin-1-yl-phenyl)-benzamide as a hydrazine compound (70 mg) produced by the above reaction was dissolved in anhydrous toluene (1.0 ml). 3,4-Dimethylbenzaldehyde (compound C) (40 μl) was added to the solution at room temperature, and the mixture was stirred at 70° C. for 15 hr. After the completion of the reaction, the reaction product was purified by column chromatography eluted with a chloroform-methanol system to give the title compound 858 (62 mg, yield 70%).

¹H-NMR (CDCl₃, 400 MHz): δ 1.04 (6H, t, J=7.2 Hz), 1.26 (2H, m), 1.37 (4H, m), 2.26 (9H, m), 2.60 (6H, m), 2.69 (2H, m), 2.84 (4H, m), 3.62 (2H, s), 6.86 (1H, d, J=8.8 Hz), 7.00 (1H, s), 7.15 (1H, d, J=7.6 Hz), 7.44 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.53 (2H, m), 7.65 (1H, s), 7.89 (1H, d, J=7.6 Hz), 7.98 (1H, s), 8.10 (1H, d, J=8.8 Hz), 8.51 (1H, s), 11.23 (2H, m)

Mass spectrometric value (ESI-MS) 595 (M−1)

Compound 859 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[2-(4-methyl-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-benzamide

The title compound 859 was produced in substantially the same manner as in Example F.

¹H-NMR (CDCl₃, 400 MHz): δ 1.05 (6H, t, J=7.2 Hz), 1.29 (2H, m), 1.40 (4H, m), 2.25 (3H, s), 2.37 (3H, s), 2.62 (6H, m), 2.72 (2H, m), 2.87 (4H, m), 3.62 (2H, s), 6.89 (1H, d, J=8.8 Hz), 7.02 (1H, s), 7.20 (2H, d, J=7.8 Hz), 7.43 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.53 (1H, d, J=7.3 Hz), 7.72 (2H, d, J=7.6 Hz), 7.88 (1H, d, J=7.6 Hz), 7.97 (1H, s), 8.13 (1H, d, J=9.0 Hz), 8.51 (1H, s), 11.23 (2H, m)

Mass spectrometric value (ESI-MS) 581 (M−1)

Compound 860 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[2-(4-fluoro-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-benzamide

The title compound 860 was produced in substantially the same manner as in Example F.

¹H-NMR (CDCl₃, 400 MHz): δ 1.05 (6H, t, J=7.1 Hz), 1.28 (2H, m), 1.37 (4H, m), 2.25 (3H, s), 2.62 (6H, m), 2.72 (2H, m), 2.84 (4H, m), 3.63 (2H, s), 6.87 (1H, d, J=8.5 Hz), 6.99 (1H, m), 7.09 (2H, dd, J=8.5 Hz, J=8.5 Hz), 7.44 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.54 (1H, d, J=7.3 Hz), 7.83 (2H, m), 7.88 (1H, d, J=7.4 Hz), 7.98 (1H, s), 8.07 (1H, d, J=9.0 Hz), 8.56 (1H, s), 11.19 (1H, s)

Mass spectrometric value (ESI-MS) 585 (M−1)

Compound 861 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[2-(3-fluoro-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-benzamide

The title compound 861 was produced in substantially the same manner as in Example F.

¹H-NMR (CDCl₃, 400 MHz): δ 1.10 (6H, t, J=7.0 Hz), 1.30 (2H, m), 1.39 (4H, m), 2.25 (3H, s), 2.64-2.90 (12H, m), 3.62 (2H, s), 6.89 (1H, d, J=8.5 Hz), 7.07 (2H, m), 7.27-7.65 (4H, m), 7.68-8.00 (3H, m), 8.11 (1H, d, J=9.0 Hz), 8.53 (1H, s), 11.23 (1H, s)

Mass spectrometric value (ESI-MS) 585 (M−1)

Compound 862 N-[2-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-3-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 862 was produced in substantially the same manner as in Example F.

¹H-NMR (CDCl₃, 400 MHz): δ 1.03 (6H, t, J=7.2 Hz), 1.23 (2H, m), 1.32 (4H, m), 2.27 (3H, s), 2.58 (6H, m), 2.67 (2H, m), 2.79 (4H, m), 3.64 (2H, s), 6.81 (1H, d, J=8.5 Hz), 6.92 (1H, s), 7.47 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.57 (2H, m), 7.88 (1H, d, J=7.8 Hz), 7.95 (1H, d, J=9.0 Hz), 8.01 (1H, s), 8.06 (1H, d, J=8.1 Hz), 8.10 (1H, s), 8.64 (1H, s), 11.08 (1H, s)

Mass spectrometric value (ESI-MS) 669 (M−1)

Compound 863 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[2-(4-methoxy-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-benzamide

The title compound 863 was produced in substantially the same manner as in Example F.

¹H-NMR (CDCl₃, 400 MHz): δ 1.06 (6H, t, J=7.1 Hz), 1.32 (2H, m), 1.43 (4H, m), 2.24 (3H, s), 2.62 (6H, m), 2.72 (2H, m), 2.90 (4H, m), 3.62 (2H, s), 3.82 (3H, s), 6.83-6.95 (3H, m), 7.05 (1H, s), 7.42 (1H, m), 7.52 (1H, m), 7.74 (2H, d, J=8.6 Hz), 7.88 (1H, d, J=7.6 Hz), 7.96 (1H, s), 8.18 (1H, d, J=9.0 Hz), 8.48 (1H, s)

Mass spectrometric value (ESI-MS) 597 (M−1)

Compound 864 N-[2-(3,4-Dimethyl-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-3-[4-(2-hydroxy-ethyl)-piperazin-1-ylmethyl]-benzamide

The title compound 864 was produced in substantially the same manner as in Example F.

¹H-NMR (CDCl₃, 400 MHz): δ 1.42 (4H, m), 1.32 (2H, m), 2.28 (3H, s), 2.29 (3H, s), 2.48-2.72 (10H, m), 2.88 (4H, m), 3.61 (4H, m), 6.92 (1H, m), 6.99 (1H, m), 7.16 (1H, d, J=7.8 Hz), 7.44 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.51 (2H, m), 7.65 (1H, s), 7.90 (1H, d, J=7.8 Hz), 7.99 (1H, s), 8.17 (1H, d, J=9.2 Hz), 8.43 (1H, s), 10.71 (1H, s), 11.21 (1H, s)

Mass spectrometric value (ESI-MS) 595 (M−1)

Compound 865 3-[4-(2-Hydroxy-ethyl)-piperazin-1-ylmethyl]-N-[2-(4-methyl-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-benzamide

The title compound 865 was produced in substantially the same manner as in Example F.

¹H-NMR (CDCl₃, 400 MHz): δ 1.28 (2H, m), 1.39 (4H, m), 2.36 (3H, s), 2.48-2.90 (14H, m), 3.60 (4H, m), 6.88 (1H, d, J=9.0 Hz), 6.99 (1H, s), 7.20 (2H, d, J=8.0 Hz), 7.44 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.51 (1H, d, J=7.3 Hz), 7.72 (2H, d, J=7.8 Hz), 7.90 (1H, d, J=7.6 Hz), 7.99 (1H, s), 8.13 (1H, d, J=9.0 Hz), 8.49 (1H, s), 10.95 (1H, s), 11.23 (1H, s)

Mass spectrometric value (ESI-MS) 581 (M−1)

Compound 866 N-[2-(4-Fluoro-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-3-[4-(2-hydroxy-ethyl)-piperazin-1-ylmethyl]-benzamide

The title compound 866 was produced in substantially the same manner as in Example F.

¹H-NMR (CDCl₃, 400 MHz): δ 1.27 (2H, m), 1.37 (4H, m), 2.55-2.90 (14H, m), 3.62 (2H, s), 3.68 (2H, t, J=5.2 Hz), 6.88 (1H, d, J=8.8 Hz), 7.00-7.16 (2H, m), 7.31-7.60 (4H, m), 7.70-8.03 (3H, m), 8.11 (1H, d, J=9.0 Hz), 8.52 (1H, s), 11.21 (1H, s), 11.35 (1H, s)

Mass spectrometric value (ESI-MS) 585 (M−1)

Compound 867 N-[2-(3-Fluoro-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-3-[4-(2-hydroxy-ethyl)-piperazin-1-ylmethyl]-benzamide

The title compound 867 was produced in substantially the same manner as in Example F.

¹H-NMR (CDCl₃, 400 MHz): δ 1.26 (2H, m), 1.36 (4H, m), 2.58 (10H, m), 2.83 (4H, m), 3.62 (4H, m), 6.87 (1H, d, J=8.8 Hz), 6.98 (1H, s), 7.08 (2H, dd, J=8.4 Hz, J=8.4 Hz), 7.44 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.52 (1H, d, J=7.8 Hz), 7.81 (2H, m), 7.89 (1H, d, J=7.6 Hz), 7.98 (1H, s), 8.09 (1H, d, J=9.0 Hz), 8.53 (1H, s), 11.20 (1H, s)

Mass spectrometric value (ESI-MS) 585 (M−1)

Compound 868 N-[2-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-3-[4-(2-hydroxy-ethyl)-piperazin-1-ylmethyl]-benzamide

The title compound 868 was produced in substantially the same manner as in Example F.

¹H-NMR (CD₃OD, 400 MHz): δ 1.61 (2H, m), 1.72 (4H, m), 2.46-2.65 (10H, m), 3.22 (4H, m), 3.63 (4H, m), 7.20 (1H, dd, J=9.3 Hz, J=2.7 Hz), 7.36 (1H, d, J=2.7 Hz), 7.48 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.55 (1H, d, J=7.8 Hz), 7.65 (1H, d, J=8.3 Hz), 7.86 (1H, m), 7.93 (1H, m), 8.00 (1H, d, J=8.3 Hz), 8.26 (1H, s), 8.32 (1H, d, J=9.3 Hz), 8.36 (1H, s)

Mass spectrometric value (ESI-MS) 669 (M−1)

Compound 869 3-[4-(2-Hydroxy-ethyl)-piperazin-1-ylmethyl]-N-[2-(4-methoxy-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-benzamide

The title compound 869 was produced in substantially the same manner as in Example F.

¹H-NMR (CDCl₃, 400 MHz): δ 1.37 (2H, m), 1.48 (4H, m), 2.56 (10H, m), 2.93 (4H, m), 3.61 (4H, m), 3.84 (3H, s), 6.90-7.04 (4H, m), 7.44 (1H, dd, J=7.4 Hz, J=7.4 Hz), 7.51 (1H, d, J=7.4 Hz), 7.76 (2H, d, J=8.3 Hz), 7.89 (1H, d, J=7.6 Hz), 7.98 (1H, s), 8.23 (1H, m), 8.38 (1H, m), 11.21 (1H, s)

Mass spectrometric value (ESI-MS) 597 (M−1)

Compound 870 N-[2-(3,4-Dimethyl-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-3-(4-hydroxy-piperidin-1-ylmethyl)-benzamide

The title compound 870 was produced in substantially the same manner as in Example F.

¹H-NMR (CDCl₃, 400 MHz): δ 1.32 (2H, m), 1.43 (4H, m), 1.63 (2H, m), 1.90 (2H, m), 2.29 (8H, m), 2.80 (2H, m), 2.88 (4H, m), 3.63 (2H, s), 3.72 (1H, m), 6.91 (1H, d, J=8.8 Hz), 7.02 (1H, s), 7.15 (1H, d, J=7.8 Hz), 7.35-7.55 (3H, m), 7.65 (1H, m), 7.90 (1H, d, J=7.3 Hz), 7.97 (1H, s), 8.18 (1H, d, J=9.3 Hz), 8.44 (1H, s), 10.79 (1H, s), 11.24 (1H, s)

Mass spectrometric value (ESI-MS) 566 (M−1)

Compound 871 3-(4-Hydroxy-piperidin-1-ylmethyl)-N-[2-(4-methyl-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-benzamide

The title compound 871 was produced in substantially the same manner as in Example F.

¹H-NMR (CDCl₃, 400 MHz): δ 1.26 (2H, m), 1.40 (4H, m), 1.64 (2H, m), 1.89 (2H, m), 2.26 (2H, m), 2.35 (3H, s), 2.82 (6H, m), 3.63 (2H, s), 3.71 (1H, m), 6.89 (1H, d, J=8.6 Hz), 7.04 (1H, s), 7.18 (2H, d, J=7.8 Hz), 7.43 (1H, m), 7.53 (1H, m), 7.69 (2H, d, J=7.6 Hz), 7.90 (1H, d, J=7.3 Hz), 7.97 (1H, s), 8.17 (1H, d, J=8.6 Hz), 8.47 (1H, s), 10.98 (1H, s), 11.26 (1H, s)

Mass spectrometric value (ESI-MS) 552 (M−1)

Compound 872 N-[2-(4-Fluoro-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-3-(4-hydroxy-piperidin-1-ylmethyl)-benzamide

The title compound 872 was produced in substantially the same manner as in Example F.

¹H-NMR (CDCl₃, 400 MHz): δ 1.32 (2H, m), 1.42 (4H, m), 1.66 (2H, m), 1.92 (2H, m), 2.40 (2H, m), 2.88 (6H, m), 3.71 (2H, s), 3.76 (1H, m), 6.90 (1H, d, J=8.8 Hz), 6.98-7.11 (2H, m), 7.43 (1H, m), 7.54 (1H, m), 7.77 (2H, m), 7.89 (1H, d, J=7.6 Hz), 7.96 (1H, s), 8.05 (1H, m), 8.15 (1H, d, J=9.0 Hz), 8.47 (1H, s), 11.10-11.30 (2H, m)

Mass spectrometric value (ESI-MS) 556 (M−1)

Compound 873 N-[2-(3-Fluoro-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-3-(4-hydroxy-piperidin-1-ylmethyl)-benzamide

The title compound 873 was produced in substantially the same manner as in Example F.

¹H-NMR (CDCl₃, 400 MHz): δ 1.34 (2H, m), 1.44 (4H, m), 1.67 (2H, m), 1.94 (2H, m), 2.34 (2H, m), 2.88 (6H, m), 3.70 (2H, s), 3.77 (1H, m), 6.92 (1H, d, J=8.3 Hz), 7.09 (3H, m), 7.29-7.67 (4H, m), 7.90 (1H, d, J=7.8 Hz), 7.97 (1H, s), 8.14 (1H, d, J=9.0 Hz), 8.49 (1H, s), 11.02 (1H, s), 11.17 (1H, s)

Mass spectrometric value (ESI-MS) 556 (M−1)

Compound 874 N-[2-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-3-(4-hydroxy-piperidin-1-ylmethyl)-benzamide

The title compound 874 was produced in substantially the same manner as in Example F.

¹H-NMR (CD₃OD, 400 MHz): δ 1.50-1.68 (4H, m), 1.75 (4H, m), 1.84 (2H, m), 2.22 (2H, m), 2.81 (2H, m), 3.24 (4H, t, J=5.2 Hz), 3.61 (3H, m), 7.22 (1H, dd, J=9.0 Hz, J=2.7 Hz), 7.37 (1H, d, J=2.7 Hz), 7.50 (1H, m), 7.57 (1H, m), 7.67 (1H, d, J=8.3 Hz), 7.87 (1H, d, J=7.8 Hz), 7.92 (1H, s), 8.03 (1H, d, J=8.3 Hz), 8.29 (1H, s), 8.33 (1H, d, J=9.0 Hz), 8.37 (1H, s)

Mass spectrometric value (ESI-MS) 640 (M−1)

Compound 875 3-(4-Hydroxy-piperidin-1-ylmethyl)-N-[2-(4-methoxy-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-benzamide

The title compound 875 was produced in substantially the same manner as in Example F.

¹H-NMR (CDCl₃, 400 MHz): δ 1.34 (2H, m), 1.45 (4H, m), 1.64 (2H, m), 1.90 (2H, m), 2.25 (2H, m), 2.79 (2H, m), 2.91 (4H, m), 3.63 (2H, s), 3.72 (1H, m), 3.83 (3H, m), 6.92 (3H, m), 7.64 (1H, s), 7.33-7.50 (1H, m), 7.53 (1H, d, J=7.6 Hz), 7.75 (2H, d, J=8.3 Hz), 7.89 (1H, d, J=7.6 Hz), 7.96 (1H, s), 8.22 (1H, d, J=8.8 Hz), 8.42 (1H, s), 10.68 (1H, bs), 11.25 (1H, s)

Mass spectrometric value (ESI-MS) 568 (M−1)

Compound 876 3-(2-Diethylamino-ethylsulfanylmethyl)-N-[2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-benzamide

The title compound 876 was produced in substantially the same manner as in Example F.

¹H-NMR (CDCl₃, 400 MHz): δ 1.03 (6H, t, J=7.1 Hz), 1.33 (2H, m), 1.44 (4H, m), 2.29 (6H, m), 2.59 (6H, m), 2.71 (2H, m), 2.90 (4H, m), 3.84 (2H, s), 6.92 (1H, d, J=8.8 Hz), 7.10 (1H, s), 7.16 (1H, d, J=7.6 Hz), 7.44 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.53 (2H, m), 7.66 (1H, m), 7.89 (1H, d, J=7.6 Hz), 8.00 (1H, s), 8.18 (1H, d, J=8.8 Hz), 8.44 (1H, s), 10.73 (1H, bs), 11.26 (1H, s)

Mass spectrometric value (ESI-MS) 598 (M−1)

Compound 877 3-(2-Diethylamino-ethylsulfanylmethyl)-N-[2-(4-fluoro-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-benzamide

The title compound 877 was produced in substantially the same manner as in Example F.

¹H-NMR (CDCl₃, 400 MHz): δ 1.08 (6H, t, J=7.0 Hz), 1.36 (2H, m), 1.46 (4H, m), 2.74 (6H, m), 2.84 (2H, m), 2.92 (4H, m), 3.83 (2H, s), 6.94 (1H, d, J=8.3 Hz), 7.05 (2H, m), 7.42 (1H, d, J=7.7 Hz, J=7.7 Hz), 7.52 (1H, m), 7.79 (2H, m), 7.88 (1H, d, J=7.6 Hz), 7.98 (1H, s), 8.03 (1H, m), 8.17 (1H, d, J=8.8 Hz), 8.47 (1H, s), 11.02 (1H, bs), 11.27 (1H, s)

Mass spectrometric value (ESI-MS) 588 (M−1)

Compound 878 N-[2-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-3-(2-diethylamino-ethylsulfanylmethyl)-benzamide

The title compound 878 was produced in substantially the same manner as in Example F.

¹H-NMR (CDCl₃, 400 MHz): δ 1.03 (6H, m), 1.29 (2H, m), 1.38 (4H, m), 2.48-2.75 (8H, m), 2.84 (4H, m), 3.85 (2H, s), 6.90 (2H, m), 7.47 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.56 (2H, m), 7.88 (1H, d, J=7.8 Hz), 8.00-8.12 (4H, m), 8.60 (1H, s), 11.07 (2H, m)

Mass spectrometric value (ESI-MS) 672 (M−1)

Compound 879 3-(2-Diethylamino-ethylsulfanylmethyl)-N-[2-(4-methoxy-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-benzamide

The title compound 879 was produced in substantially the same manner as in Example F.

¹H-NMR (CDCl₃, 400 MHz): δ 1.02 (6H, t, J=7.1 Hz), 1.26 (2H, m), 1.67 (4H, m), 2.59 (6H, m), 2.70 (2H, m), 2.92 (4H, m), 3.83 (5H, m), 6.92 (3H, m), 7.02 (1H, s), 7.44 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.53 (1H, d, J=7.6 Hz), 7.77 (2H, d, J=8.3 Hz), 7.88 (1H, d, J=7.6 Hz), 7.99 (1H, m), 8.22 (1H, d, J=8.8 Hz), 8.42 (1H, s), 10.59 (1H, bs), 11.27 (1H, s)

Mass spectrometric value (ESI-MS) 600 (M−1)

Compound 880 N-[2-(3,4-Dimethyl-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-3-(2-hydroxy-ethylsulfanylmethyl)-benzamide

The title compound 880 was produced in substantially the same manner as in Example F.

¹H-NMR (CDCl₃, 400 MHz): δ 1.41 (2H, m), 1.51 (4H, m), 2.24 (3H, s), 2.67 (3H, s), 2.65 (2H, t, J=6.9 Hz), 2.94 (4H, m), 3.82 (2H, s), 3.93 (1H, t, J=6.8 Hz), 6.93 (1H, d, J=9.0 Hz), 7.04 (1H, s), 7.14 (1H, d, J=7.8 Hz), 7.52 (3H, m), 7.63 (1H, s), 7.80 (1H, s), 8.01 (1H, d, J=6.8 Hz), 8.25 (1H, s), 8.28 (2H, d, J=9.0 Hz), 10.56 (1H, s), 11.50 (1H, s)

Mass spectrometric value (ESI-MS) 543 (M−1)

Compound 881 3-(2-Hydroxy-ethylsulfanylmethyl)-N-[2-(4-methyl-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-benzamide

The title compound 881 was produced in substantially the same manner as in Example F.

¹H-NMR (CDCl₃, 400 MHz): δ 1.43 (2H, m), 1.54 (4H, m), 2.33 (3H, s), 2.64 (2H, t, J=7.1 Hz), 2.97 (4H, m), 3.82 (2H, s), 3.92 (2H, m), 6.95 (1H, m), 7.08 (1H, s), 7.19 (2H, d, J=7.8 Hz), 7.54 (2H, m), 7.69 (2H, d, J=7.8 Hz), 7.79 (1H, s), 8.00 (1H, d, J=7.1 Hz), 8.26 (1H, s), 8.30 (1H, d, J=9.3 Hz), 10.52 (1H, s), 11.49 (1H, s)

Mass spectrometric value (ESI-MS) 529 (M−1)

Compound 882 N-[2-(4-Fluoro-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-3-(2-hydroxy-ethylsulfanylmethyl)-benzamide

The title compound 882 was produced in substantially the same manner as in Example F.

¹H-NMR (CDCl₃, 400 MHz): δ 1.44 (2H, m), 1.57 (4H, m), 2.64 (2H, t, J=7.0 Hz), 2.99 (4H, m), 3.81 (2H, s), 3.91 (2H, m), 7.00 (1H, d, J=8.8 Hz), 7.10 (2H, dd, J=8.7 Hz, J=8.7 Hz), 7.15 (1H, s), 7.54 (2H, m), 7.78 (1H, s), 7.86 (2H, m), 8.06 (1H, d, J=7.1 Hz), 8.33 (2H, m), 10.59 (1H, s), 11.48 (1H, s)

Mass spectrometric value (ESI-MS) 533 (M−1)

Compound 883 N-[2-(3-Fluoro-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-3-(2-hydroxy-ethylsulfanylmethyl)-benzamide

The title compound 883 was produced in substantially the same manner as in Example F.

¹H-NMR (CDCl₃, 400 MHz): δ 1.44 (2H, m), 1.57 (4H, m), 2.65 (2H, t, J=6.9 Hz), 2.99 (4H, m), 3.82 (2H, s), 3.92 (2H, m), 6.80-7.22 (3H, m), 7.36 (1H, m), 7.53 (3H, m), 7.66 (1H, m), 7.80 (1H, s), 8.00 (1H, d, J=6.6 Hz), 8.30 (2H, m), 10.65 (1H, s), 11.46 (1H, s)

Mass spectrometric value (ESI-MS) 533 (M−1)

Compound 884 N-[2-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-3-(2-hydroxy-ethylsulfanylmethyl)-benzamide

The title compound 884 was produced in substantially the same manner as in Example F.

¹H-NMR (CDCl₃, 400 MHz): δ 1.36 (2H, m), 1.44 (4H, m), 2.65 (2H, t, J=7.2 Hz), 2.86 (4H, m), 3.82 (2H, s), 3.92 (2H, t, J=7.1 Hz), 6.90 (1H, d, J=8.0 Hz), 6.97 (1H, s), 7.57 (3H, m), 7.76 (1H, s), 8.04 (2H, d, J=6.8 Hz), 8.14 (1H, d, J=9.8 Hz), 8.23 (1H, s), 8.43 (1H, s), 11.09 (1H, s), 11.38 (1H, s)

Mass spectrometric value (ESI-MS) 617 (M−1)

Compound 885 3-(2-Hydroxy-ethylsulfanylmethyl)-N-[2-(4-methoxy-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-benzamide

The title compound 885 was produced in substantially the same manner as in Example F.

¹H-NMR (CDCl₃, 400 MHz): δ 1.47 (2H, m), 1.62 (4H, m), 2.64 (2H, t, J=7.1 Hz), 3.04 (4H, m), 3.80 (3H, s), 3.81 (2H, s), 3.92 (2H, m), 6.89 (2H, d, J=8.8 Hz), 7.02 (1H, m), 7.24 (1H, m), 7.52 (2H, m), 7.76 (3H, m), 7.99 (1H, d, J=7.3 Hz), 8.25 (1H, s), 8.40 (1H, d, J=9.0 Hz), 10.50 (1H, s), 11.59 (1H, s)

Mass spectrometric value (ESI-MS) 545 (M−1)

Compound 886 3-{3-[2-(3,4-Dimethyl-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenylcarbamoyl]-benzylsulfanyl}-propionic acid

The title compound 886 was produced in substantially the same manner as in Example F.

¹H-NMR (CDCl₃, 400 MHz): δ 1.37 (2H, m), 1.52 (4H, m), 2.20 (6H, s), 2.75 (2H, m), 2.84 (2H, m), 2.94 (4H, m), 3.94 (2H, s), 6.93 (1H, d, J=7.8 Hz), 7.06 (1H, d, J=7.6 Hz), 7.11 (1H, s), 7.38-7.52 (3H, m), 7.55 (1H, s), 7.94 (1H, s), 8.02 (1H, d, J=6.8 Hz), 8.25 (1H, d, J=9.0 Hz), 8.28 (1H, s), 10.85 (1H, s), 11.36 (1H, s)

Mass spectrometric value (ESI-MS) 571 (M−1)

Compound 887 3-{3-[2-(4-Methyl-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenylcarbamoyl]-benzylsulfanyl}-propionic acid

The title compound 887 was produced in substantially the same manner as in Example F.

¹H-NMR (CDCl₃, 400 MHz): δ 1.33 (2H, m), 1.47 (4H, m), 2.29 (3H, s), 2.70 (2H, t, J=6.4 Hz), 2.80 (2H, t, J=6.3 Hz), 2.90 (4H, m), 3.89 (2H, s), 6.91 (1H, d, J=8.8 Hz), 7.12 (3H, m), 7.40-7.50 (2H, m), 7.61 (2H, d, J=7.8 Hz), 7.93 (1H, s), 7.97 (1H, d, J=7.3 Hz), 8.20 (1H, d, J=9.0 Hz), 8.35 (1H, s), 11.03 (1H, s), 11.32 (1H, s)

Mass spectrometric value (ESI-MS) 557 (M−1)

Compound 888 3-{3-[2-(4-Fluoro-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenylcarbamoyl]-benzylsulfanyl}-propionic acid

The title compound 888 was produced in substantially the same manner as in Example F.

¹H-NMR (CD₃OD, 400 MHz): δ 1.62 (2H, m), 1.74 (4H, m), 2.55 (2H, t, J=6.8 Hz), 2.68 (2H, t, J=7.0 Hz), 3.23 (4H, m), 3.86 (2H, s), 7.10-7.25 (3H, m), 7.36 (1H, d, J=2.9 Hz), 7.47 (1H, dd, J=7.1 Hz, J=7.1 Hz), 7.57 (1H, d, J=7.3 Hz), 7.85 (3H, m), 7.93 (1H, m), 8.32 (2H, m)

Mass spectrometric value (ESI-MS) 561 (M−1)

Compound 889 3-{3-[2-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenylcarbamoyl]-benzylsulfanyl}-propionic acid

The title compound 889 was produced in substantially the same manner as in Example F.

¹H-NMR (CD₃OD, 400 MHz): δ 1.62 (2H, m), 1.74 (4H, m), 2.54 (2H, t, J=7.0 Hz), 2.68 (2H, t, J=7.0 Hz), 3.22 (4H, m), 3.86 (2H, s), 7.22 (1H, m), 7.36 (1H, m), 7.48 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.57 (1H, m), 7.67 (1H, m), 7.83 (1H, d, J=7.3 Hz), 7.93 (1H, s), 8.03 (1H, d, J=9.0 Hz), 8.29 (2H, m), 8.36 (1H, m)

Mass spectrometric value (ESI-MS) 646 (M−1)

Compound 890 3-{3-[2-(4-Methoxy-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenylcarbamoyl]-benzylsulfanyl}-propionic acid

The title compound 890 was produced in substantially the same manner as in Example F.

¹H-NMR (CDCl₃, 400 MHz): δ 1.35 (2H, m), 1.49 (4H, m), 2.71 (2H, m), 2.80 (2H, m), 2.92 (4H, m), 3.76 (3H, s), 3.89 (2H, s), 6.80 (2H, d, J=8.8 Hz), 6.92 (1H, d, J=7.3 Hz), 7.15 (1H, s), 7.45 (2H, m), 7.64 (2H, d, J=8.6 Hz), 7.95 (2H, m), 8.24 (1H, d, J=9.0 Hz), 8.31 (1H, s), 10.97 (1H, bs), 11.37 (1H, s)

Mass spectrometric value (ESI-MS) 573 (M−1)

Compound 891 {3-[2-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenylcarbamoyl]-benzylsulfanyl}-acetic acid

The title compound 891 was produced in substantially the same manner as in Example F.

¹H-NMR (CD₃OD, 400 MHz): δ 1.63 (2H, m), 1.75 (4H, m), 3.11 (2H, s), 3.24 (4H, m), 3.94 (2H, s), 7.22 (1H, dd, J=9.2 Hz, J=2.8 Hz), 7.37 (1H, d, J=2.7 Hz), 7.48 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.58 (1H, d, J=8.0 Hz), 7.67 (1H, d, J=8.3 Hz), 7.84 (1H, d, J=8.0 Hz), 7.95 (1H, s), 8.03 (1H, d, J=8.6 Hz), 8.28 (2H, m), 8.37 (1H, s)

Mass spectrometric value (ESI-MS) 631 (M−1)

Compound 892 {3-[2-(4-Methoxy-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenylcarbamoyl]-benzylsulfanyl}-acetic acid

The title compound 892 was produced in substantially the same manner as in Example F.

¹H-NMR (CDCl₃, 400 MHz): δ 1.39 (2H, m), 1.53 (4H, m), 2.93 (4H, m), 3.21 (2H, s), 3.77 (3H, s), 3.98 (2H, s), 6.82 (2H, d, J=8.6 Hz), 6.93 (1H, d, J=9.3 Hz), 7.22 (1H, s), 7.48 (2H, m), 7.63 (2H, d, J=8.3 Hz), 7.82 (1H, s), 7.98 (1H, d, J=7.1 Hz), 8.25 (1H, d, J=8.8 Hz), 8.32 (1H, s), 10.93 (1H, s), 11.43 (1H, s)

Mass spectrometric value (ESI-MS) 559 (M−1)

Compound 893 3-(7,8-Dihydro-5H-1,6,9-triaza-anthracen-6-ylmethyl)-N-[2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-benzamide

The title compound 893 was produced in substantially the same manner as in Example F.

¹H-NMR (CDCl₃, 400 MHz): δ 1.32 (2H, m), 1.40 (4H, m), 2.22 (6H, s), 2.83 (4H, m), 2.97 (2H, t, J=5.7 Hz), 3.31 (2H, t, J=6.0 Hz), 3.84 (4H, s), 6.92 (1H, d, J=9.0 Hz), 7.09 (2H, m), 7.35 (1H, m), 7.45 (2H, m), 7.61 (2H, m), 7.77 (1H, s), 7.95 (1H, d, J=7.3 Hz), 8.02 (2H, m), 8.26 (1H, d, J=9.0 Hz), 8.49 (1H, s), 8.97 (1H, dd, J=4.3 Hz, J=1.8 Hz), 11.05 (1H, s), 11.41 (1H, s)

Mass spectrometric value (ESI-MS) 650 (M−1)

Compound 894 3-(7,8-Dihydro-5H-1,6,9-triaza-anthracen-6-ylmethyl)-N-[2-(4-methyl-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-benzamide

The title compound 894 was produced in substantially the same manner as in Example F.

¹H-NMR (CDCl₃, 400 MHz): δ 1.31 (2H, m), 1.39 (4H, m), 2.33 (3H, s), 2.82 (4H, m), 2.97 (2H, m), 3.31 (2H, t, J=6.0 Hz), 3.84 (4H, m), 6.92 (1H, d, J=8.1 Hz), 7.07 (1H, s), 7.15 (2H, d, J=8.1 Hz), 7.35 (1H, m), 7.47 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.60 (1H, d, J=7.3 Hz), 7.65 (2H, d, J=7.1 Hz), 7.77 (1H, s), 7.94 (1H, d, J=7.3 Hz), 8.02 (2H, m), 8.26 (1H, d, J=9.0 Hz), 8.52 (1H, s), 8.97 (1H, dd, J=4.3 Hz, J=1.8 Hz), 11.08 (1H, s), 11.39 (1H, s)

Mass spectrometric value (ESI-MS) 636 (M−1)

Compound 895 3-(7,8-Dihydro-5H-1,6,9-triaza-anthracen-6-ylmethyl)-N-[2-(4-fluoro-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-benzamide

The title compound 895 was produced in substantially the same manner as in Example F.

¹H-NMR (CDCl₃, 400 MHz): δ 1.20-1.40 (6H, m), 2.75 (4H, m), 2.94 (2H, m), 3.25 (2H, m), 3.82 (2H, s), 3.83 (2H, s), 6.89 (1H, d, J=8.8 Hz), 7.00 (2H, m), 7.10 (1H, s), 7.37 (1H, m), 7.46 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.59 (1H, d, J=7.3 Hz), 7.70 (2H, m), 7.77 (1H, s), 7.94 (1H, d, J=7.8 Hz), 8.04 (2H, m), 8.26 (1H, d, J=9.0 Hz), 8.61 (1H, s), 8.94 (1H, m), 11.45-11.75 (2H, m)

Mass spectrometric value (ESI-MS) 640 (M−1)

Compound 896 3-(7,8-Dihydro-5H-1,6,9-triaza-anthracen-6-ylmethyl)-N-[2-(3-fluoro-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-benzamide

The title compound 896 was produced in substantially the same manner as in Example F.

¹H-NMR (CDCl₃, 400 MHz): δ 1.29 (2H, m), 1.36 (4H, m), 2.79 (4H, m), 2.97 (2H, m), 3.28 (2H, t, J=6.0 Hz), 3.84 (2H, s), 3.85 (2H, s), 6.90 (1H, d, J=8.3 Hz), 7.03 (1H, m), 7.09 (1H, s), 7.28-8.00 (5H, m), 7.61 (1H, d, J=7.3 Hz), 7.77 (1H, s), 7.94 (1H, d, J=7.6 Hz), 8.05 (2H, m), 8.22 (1H, d, J=9.0 Hz), 8.60 (1H, s), 8.97 (1H, dd, J=4.1 Hz, J=2.0 Hz), 11.38 (1H, s), 11.55 (1H, s)

Mass spectrometric value (ESI-MS) 640 (M−1)

Compound 897 N-[2-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-3-(7,8-dihydro-5H-1,6,9-triaza-anthracen-6-ylmethyl)-benzamide

The title compound 897 was produced in substantially the same manner as in Example F.

¹H-NMR (CDCl₃, 400 MHz): δ 1.30 (2H, m), 1.37 (4H, m), 2.80 (4H, m), 2.97 (2H, t, J=5.9 Hz), 3.30 (2H, t, J=5.9 Hz), 3.86 (4H, m), 6.90 (1H, d, J=8.3 Hz), 7.02 (1H, s), 7.38 (1H, m), 7.51 (2H, d, J=8.3 Hz), 7.62 (1H, d, J=8.3 Hz), 7.78 (1H, s), 7.94 (2H, d, J=7.3 Hz), 8.00 (1H, s), 8.06 (2H, m), 8.17 (1H, d, J=8.3 Hz), 8.61 (1H, s), 8.98 (1H, m), 11.25 (1H, s), 11.46 (1H, s)

Mass spectrometric value (ESI-MS) 724 (M−1)

Compound 898 3-(7,8-Dihydro-5H-1,6,9-triaza-anthracen-6-ylmethyl)-N-[2-(4-methoxy-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-benzamide

The title compound 898 was produced in substantially the same manner as in Example F.

¹H-NMR (CDCl₃, 400 MHz): δ 1.31 (2H, m), 1.39 (4H, m), 2.83 (4H, m), 2.97 (2H, m), 3.30 (2H, t, J=5.6 Hz), 3.78 (5H, m), 3.83 (2H, s), 6.85 (2H, d, J=8.0 Hz), 6.92 (1H, d, J=7.1 Hz), 7.09 (1H, s), 7.35 (1H, m), 7.46 (1H, t, J=7.7 Hz), 7.59 (1H, d, J=7.6 Hz), 7.67 (2H, d, J=7.8 Hz), 7.76 (1H, s), 7.94 (1H, d, J=7.6 Hz), 8.02 (2H, m), 8.28 (1H, d, J=9.0 Hz), 8.49 (1H, s), 8.96 (1H, m), 11.08 (1H, bs), 11.44 (1H, s)

Mass spectrometric value (ESI-MS) 652 (M−1)

Compound 899 3-(2,3-Dihydroxy-propylsulfanylmethyl)-N-[2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-benzamide

The title compound 899 was produced in substantially the same manner as in Example F.

¹H-NMR (CD₃OD, 400 MHz): δ 1.62 (2H, m), 1.75 (4H, m), 2.29 (3H, s), 2.31 (3H, s), 2.50 (1H, m), 2.63 (1H, m), 3.23 (4H, m), 3.56 (2H, m), 3.74 (1H, m), 3.88 (2H, s), 7.21 (2H, m), 7.37 (1H, d, J=2.9 Hz), 7.48 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.53 (1H, d, J=7.8 Hz), 7.59 (1H, d, J=7.6 Hz), 7.65 (1H, s), 7.85 (1H, m), 7.93 (1H, m), 8.29 (1H, s), 8.37 (1H, d, J=9.2 Hz)

Mass spectrometric value (ESI-MS) 573 (M−1)

Compound 900 3-(2,3-Dihydroxy-propylsulfanylmethyl)-N-[2-(4-methyl-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-benzamide

The title compound 900 was produced in substantially the same manner as in Example F.

¹H-NMR (DMSO-d₆, 400 MHz): δ 1.57 (2H, m), 1.67 (4H, m), 2.35 (3H, s), 2.40 (1H, m), 2.58 (1H, m), 3.15-3.36 (6H, m), 3.60 (1H, m), 3.86 (2H, s), 4.55 (1H, m), 4.81 (1H, m), 7.19 (1H, m), 7.28 (2H, d, J=8.1 Hz), 7.32 (1H, d, J=2.4 Hz), 7.53 (2H, m), 7.65 (2H, d, J=8.1 Hz), 7.77 (1H, m), 7.87 (1H, s), 8.29 (1H, d, J=8.3 Hz), 8.41 (1H, s), 11.42 (1H, bs), 11.95 (1H, bs)

Mass spectrometric value (ESI-MS) 559 (M−1)

Compound 901 3-(2,3-Dihydroxy-propylsulfanylmethyl)-N-[2-(4-fluoro-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-benzamide

The title compound 901 was produced in substantially the same manner as in Example F.

¹H-NMR (CD₃OD, 400 MHz): δ 1.62 (2H, m), 1.74 (4H, m), 2.50 (1H, m), 2.62 (1H, m), 3.23 (4H, m), 3.55 (2H, m), 3.75 (1H, m), 3.88 (2H, s), 7.17 (2H, dd, J=8.7 Hz, J=8.7 Hz), 7.22 (1H, dd, J=9.0 Hz, J=2.7 Hz), 7.37 (1H, d, J=2.7 Hz), 7.48 (1H, dd, J=7.5 Hz, J=7.5 Hz), 7.58 (1H, d, J=7.6 Hz), 7.80-7.95 (4H, m), 8.34 (1H, s), 8.37 (1H, d, J=9.3 Hz)

Mass spectrometric value (ESI-MS) 563 (M−1)

Compound 902 3-(2,3-Dihydroxy-propylsulfanylmethyl)-N-[2-(3-fluoro-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-benzamide

The title compound 902 was produced in substantially the same manner as in Example F.

¹H-NMR (DMSO-d₆, 400 MHz): δ 1.57 (2H, m), 1.67 (4H, m), 2.04 (1H, m), 2.58 (1H, m), 3.19-3.40 (6H, m), 3.60 (1H, m), 3.86 (2H, s), 4.54 (1H, t, J=5.7 Hz), 4.80 (1H, d, J=3.5 Hz), 7.20 (1H, m), 7.29 (2H, m), 7.44-7.64 (5H, m), 7.76 (1H, d, J=7.6 Hz), 7.87 (1H, s), 8.25 (1H, d, J=9.0 Hz), 8.44 (1H, s), 11.30 (1H, s), 12.10 (1H, s)

Mass spectrometric value (ESI-MS) 563 (M−1)

Compound 903 N-[2-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-3-(2,3-dihydroxy-propyl-sulfanylmethyl)-benzamide

The title compound 903 was produced in substantially the same manner as in Example F.

¹H-NMR (CD₃OD, 400 MHz): δ 1.63 (2H, m), 1.75 (4H, m), 2.50 (1H, m), 2.62 (1H, m), 3.24 (4H, m), 3.54 (2H, m), 3.74 (1H, m), 3.88 (2H, s), 7.23 (1H, dd, J=9.1 Hz, J=2.8 Hz), 7.38 (1H, d, J=2.7 Hz), 7.48 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.58 (1H, d, J=7.8 Hz), 7.68 (1H, d, J=8.3 Hz), 7.84 (1H, d, J=7.8 Hz), 7.93 (1H, s), 8.06 (1H, d, J=8.3 Hz), 8.29 (1H, s), 8.34 (1H, d, J=9.0 Hz), 8.37 (1H, s)

Mass spectrometric value (ESI-MS) 647 (M−1)

Compound 904 3-(2,3-Dihydroxy-propylsulfanylmethyl)-N-[2-(4-methoxy-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-benzamide

The title compound 904 was produced in substantially the same manner as in Example F.

¹H-NMR (DMSO-d₆, 400 MHz): δ 1.57 (2H, m), 1.68 (4H, m), 2.40 (1H, m), 2.58 (1H, m), 3.15-3.40 (6H, m), 3.61 (1H, m), 3.82 (3H, s), 3.86 (2H, s), 7.02 (2H, d, J=8.8 Hz), 7.21 (1H, m), 7.33 (1H, m), 7.53 (2H, m), 7.70 (2H, d, J=8.8 Hz), 7.77 (1H, d, J=7.6 Hz), 7.87 (1H, s), 8.31 (1H, d, J=9.0 Hz), 8.39 (1H, s), 11.44 (1H, s), 11.87 (1H, s)

Mass spectrometric value (ESI-MS) 575 (M−1)

Compound 905 3-{[Bis-(2-diethylamino-ethyl)-amino]-methyl}-N-[2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-benzamide

The title compound 905 was produced in substantially the same manner as in Example F.

¹H-NMR (CDCl₃, 400 MHz): δ 0.99 (12H, t, J=7.1 Hz), 1.44 (2H, m), 1.57 (4H, m), 2.30 (6H, s), 2.50 (8H, m), 2.61 (8H, m), 3.00 (4H, m), 3.73 (2H, s), 7.02 (2H, m), 7.18 (1H, d, J=7.3 Hz), 7.42 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.51 (1H, m), 7.57 (1H, m), 7.67 (1H, s), 7.87 (1H, d, J=7.8 Hz), 7.97 (1H, s), 8.32 (2H, m), 11.14 (1H, s)

Mass spectrometric value (ESI-MS) 681 (M−1)

Compound 906 3-{[Bis-(2-diethylamino-ethyl)-amino]-methyl}-N-[2-(4-methyl-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-benzamide

The title compound 906 was produced in substantially the same manner as in Example F.

¹H-NMR (CDCl₃, 400 MHz): δ 1.00 (12H, t, J=7.2 Hz), 1.25 (2H, m), 1.34 (4H, m), 2.37 (3H, s), 2.51 (8H, m), 2.62 (8H, m), 2.80 (4H, m), 3.75 (2H, s), 6.85 (1H, m), 6.97 (1H, m), 7.20 (2H, d, J=8.0 Hz), 7.43 (1H, d, J=7.6 Hz), 7.59 (1H, d, J=7.3 Hz), 7.75 (2H, d, J=7.8 Hz), 7.86 (1H, d, J=7.8 Hz), 8.00 (1H, s), 8.08 (1H, d, J=9.0 Hz), 8.59 (1H, s), 11.20 (1H, s)

Mass spectrometric value (ESI-MS) 667 (M−1)

Compound 907 3-{[Bis-(2-diethylamino-ethyl)-amino]-methyl}-N-[2-(4-fluoro-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-benzamide

The title compound 907 was produced in substantially the same manner as in Example F.

¹H-NMR (CDCl₃, 400 MHz): δ 1.00 (12H, t, J=7.1 Hz), 1.26 (2H, m), 1.35 (4H, m), 2.51 (8H, m), 2.62 (8H, m), 2.81 (4H, m), 3.75 (2H, s), 6.85 (1H, d, J=9.0 Hz), 6.94 (1H, s), 7.10 (2H, dd, J=8.5 Hz, J=8.5 Hz), 7.44 (1H, d, J=7.6 Hz, J=7.6 Hz), 7.60 (1H, d, J=7.3 Hz), 7.85 (3H, m), 8.00 (1H, s), 8.03 (1H, d, J=9.0 Hz), 8.61 (1H, s), 11.14 (2H, m)

Mass spectrometric value (ESI-MS) 671 (M−1)

Compound 908 3-{[Bis-(2-diethylamino-ethyl)-amino]-methyl}-N-[2-(3-fluoro-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-benzamide

The title compound 908 was produced in substantially the same manner as in Example F.

¹H-NMR (CDCl₃, 400 MHz): δ 1.00 (12H, t, J=7.1 Hz), 1.24 (2H, m), 1.33 (4H, m), 2.51 (8H, m), 2.62 (8H, m), 2.78 (4H, m), 3.76 (2H, s), 6.84 (1H, d, J=9.3 Hz), 6.91 (1H, s), 7.11 (1H, m), 7.34-7.48 (2H, m), 7.58-7.68 (3H, m), 7.87 (1H, d, J=7.8 Hz), 8.00 (2H, m), 8.61 (1H, s)

Mass spectrometric value (ESI-MS) 671 (M−1)

Compound 909 3-{[Bis-(2-diethylamino-ethyl)-amino]-methyl}-N-[2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-benzamide

The title compound 909 was produced in substantially the same manner as in Example F.

¹H-NMR (CDCl₃, 400 MHz): δ 1.00 (12H, t, J=7.1 Hz), 1.21 (2H, m), 1.30 (4H, m), 2.51 (8H, m), 2.62 (8H, m), 2.75 (4H, m), 3.77 (2H, s), 6.80 (1H, d, J=8.8 Hz), 6.88 (1H, s), 7.47 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.57 (1H, d, J=8.5 Hz), 7.64 (1H, d, J=7.6 Hz), 7.86 (1H, d, J=7.6 Hz), 7.91 (1H, d, J=9.0 Hz), 8.02 (1H, s), 8.08 (1H, d, J=8.0 Hz), 8.12 (1H, s), 8.67 (1H, s)

Mass spectrometric value (ESI-MS) 754 (M−1)

Compound 910 3-{[Bis-(2-diethylamino-ethyl)-amino]-methyl}-N-[2-(4-methoxy-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-benzamide

The title compound 910 was produced in substantially the same manner as in Example F.

¹H-NMR (CDCl₃, 400 MHz): δ 1.00 (12H, t, J=7.1 Hz), 1.28 (2H, m), 1.38 (4H, m), 2.51 (8H, m), 2.61 (8H, m), 2.83 (4H, m), 3.75 (2H, s), 3.84 (3H, s), 6.85-7.00 (4H, m), 7.43 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.59 (1H, d, J=7.6 Hz), 7.79 (2H, d, J=8.5 Hz), 7.86 (1H, d, J=7.6 Hz), 7.99 (1H, s), 8.12 (1H, d, J=9.3 Hz), 8.51 (1H, s), 11.19 (1H, s)

Mass spectrometric value (ESI-MS) 682 (M−1)

Example G

Compound 911 N-[2-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-dipropylamino-phenyl]-3-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-benzamide

5-Amino-2-nitro-benzoic acid methyl ester (compound A′) (800 mg) was dissolved in dry THF (15 ml). Propionaldehyde (compound D) (870 μl) dissolved in a mixed liquid composed of 3 M sulfuric acid (4 ml) and THF (1 ml) was added to the solution at room temperature. Subsequently, sodium borohydride (231 mg) was added thereto at 0° C., and the mixture was stirred at room temperature for 3 hr. Thereafter, distilled water was added thereto, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate and was then concentrated. The residue was purified by column chromatography using a hexane-acetone system to give 2-nitro-5-propylamino-benzoic acid methyl ester as a useful intermediate (608 mg, yield 63%).

2-Nitro-5-propylamino-benzoic acid methyl ester (608 mg) produced by the above reaction was dissolved in dry THF (15 ml). Propionaldehyde (compound D) (461 μl) dissolved in a mixed liquid composed of 3 M sulfuric acid (2.1 ml) and THF (1 ml) was added to the solution at room temperature. Subsequently, sodium borohydride (145 mg) was added thereto at 0° C., and the mixture was stirred at room temperature for 3 hr. Thereafter, distilled water was added thereto, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated. The residue was purified by column chromatography using a hexane-acetone system to give 5-dipropylamino-2-nitro-benzoic acid methyl ester as a useful intermediate (149 mg, yield 21%).

5-Dipropylamino-2-nitro-benzoic acid methyl ester (467 mg) produced by the above reaction was dissolved in ethanol (5 ml), and 10% palladium-carbon (45 mg) was added to the solution. The air in the reaction system was then replaced by hydrogen, and the reaction solution was stirred at room temperature for 15 hr. After the completion of the reaction, the reaction solution was filtered through Celite. The filtrate was concentrated, and the residue was purified by column chromatography using a hexane-acetone system to give 2-amino-5-dipropylamino-benzoic acid methyl ester (compound A) (243 mg, yield 58%) as a useful intermediate.

2-Amino-5-dipropylamino-benzoic acid methyl ester (compound A) (243 mg) produced by the above reaction was dissolved in anhydrous methylene chloride (3.0 ml). Subsequently, pyridine (170 μl) and 3-(chloromethyl)benzoyl chloride (compound B) (166 μl) were added to the solution at 0° C., and the mixture was stirred at 0° C. for one hr. After the completion of the reaction, distilled water was added thereto, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated. The residue was purified by column chromatography using a hexane-acetone system to give 2-(3-chloromethyl-benzoylamino)-5-dipropylamino-benzoic acid methyl ester as a useful intermediate (280 mg, yield 64%).

2-(3-Chloromethyl-benzoylamino)-5-dipropylamino-benzoic acid methyl ester (280 mg) produced by the above reaction was dissolved in anhydrous methylene chloride (2.0 ml). Triethylamine (45 μl) and N,N-diethyl-N′-methylethylenediamine (compound B′) (50 μl) were added to the solution at room temperature, and the mixture was stirred at room temperature for 15 hr. After the completion of the reaction, water was added thereto at room temperature, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated, and the residue was purified by column chromatography using a hexane-acetone system to give 2-(3-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-benzoylamino)-5-dipropylamino-benzoic acid methyl ester as a useful intermediate (164 mg, yield 50%).

2-(3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-benzoylamino)-5-dipropylamino-benzoic acid methyl ester (164 mg) produced by the above reaction was dissolved in ethanol (5.0 ml). Hydrazine monohydrate (200 μl) was added to the solution, and the mixture was heated under reflux with stirring for 15 hr. After the completion of the reaction, water was added thereto at room temperature, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated. The residue was purified by column chromatography eluted with a chloroform-methanol system to give 3-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-N-(4-dipropylamino-2-hydrazinocarbonyl-phenyl)-benzamide as a hydrazine compound (96 mg, yield 58%).

3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-(4-dipropylamino-2-hydrazinocarbonyl-phenyl)-benzamide (47 mg) as the hydrazine compound produced by the above reaction was dissolved in anhydrous toluene (1.0 ml). 3-Trifluoromethyl-4-chlorobenzaldehyde (compound C) (40 μl) was added to the solution at room temperature, and the mixture was stirred at room temperature for 15 hr. After the completion of the reaction, the reaction product was purified by column chromatography eluted with a chloroform-methanol system to give the title compound 911 (57 mg, yield 88%).

¹H-NMR (CDCl₃, 400 MHz): δ 0.78 (6H, t, J=7.1 Hz), 1.04 (6H, t, J=7.1 Hz), 1.37 (4H, m), 2.26 (3H, s), 2.50-2.75 (8H, m), 2.85 (4H, m), 3.62 (2H, s), 6.49 (1H, d, J=7.8 Hz), 6.65 (1H, s), 7.44 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.55 (2H, m), 7.80-8.15 (5H, m), 8.63 (1H, s), 10.83 (1H, s)

Mass spectrometric value (ESI-MS) 685 (M−1)

Compound 912 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[4-dipropylamino-2-(4-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 912 was produced in substantially the same manner as in Example G.

¹H-NMR (CDCl₃, 400 MHz): δ 0.81 (6H, t, J=7.1 Hz), 1.05 (6H, t, J=7.1 Hz), 1.42 (4H, m), 2.24 (3H, s), 2.50-2.70 (8H, m), 2.95 (4H, m), 3.61 (2H, s), 3.83 (3H, s), 6.57 (1H, d, J=9.0 Hz), 6.72 (1H, s), 6.91 (2H, d, J=8.6 Hz), 7.41 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.52 (1H, d, J=7.3 Hz), 7.76 (2H, d, J=8.3 Hz), 7.85 (1H, d, J=7.6 Hz), 7.95 (1H, s), 8.05 (1H, d, J=9.0 Hz), 8.45 (1H, s), 10.93 (1H, s)

Mass spectrometric value (ESI-MS) 614 (M−1)

Compound 913 3-({2-[Bis-(2-hydroxy-ethyl)-amino]-ethylamino}-methyl)-N-[2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-benzamide

The title compound 913 was produced in substantially the same manner as in Example F.

¹H-NMR (CDCl₃, 400 MHz): δ 1.41 (2H, m), 1.52 (4H, m), 2.25 (6H, s), 2.61 (4H, m), 2.71 (2H, m), 2.77 (2H, m), 2.97 (4H, m), 3.58 (4H, t, J=4.8 Hz), 3.92 (2H, s), 6.94 (1H, m), 7.07 (1H, s), 7.13 (1H, d, J=7.8 Hz), 7.40-7.55 (3H, m), 7.60 (1H, s), 7.93 (2H, m), 8.22 (1H, d, J=8.3 Hz), 8.38 (1H, s), 11.20 (1H, s)

Mass spectrometric value (ESI-MS) 613 (M−1)

Compound 914 3-({2-[Bis-(2-hydroxy-ethyl)-amino]-ethylamino}-methyl)-N-[2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-benzamide

The title compound 914 was produced in substantially the same manner as in Example F.

¹H-NMR (CDCl₃, 400 MHz): δ 1.44 (2H, m), 1.54 (4H, m), 2.60 (4H, m), 2.73 (2H, m), 2.86 (2H, m), 3.00 (4H, m), 3.56 (4H, m), 3.97 (2H, m), 6.90 (1H, m), 7.10 (1H, m), 7.73-7.55 (4H, m), 7.92 (2H, m), 8.02 (1H, m), 8.15 (1H, m), 8.60 (1H, s)

Mass spectrometric value (ESI-MS) 687 (M−1)

Compound 915 3-({2-[Bis-(2-hydroxy-ethyl)-amino]-ethylamino}-methyl)-N-[2-(4-methoxy-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-benzamide

The title compound 915 was produced in substantially the same manner as in Example F.

¹H-NMR (CDCl₃, 400 MHz): δ 1.40 (2H, m), 1.51 (4H, m), 2.61 (4H, m), 2.70 (2H, m), 2.76 (2H, m), 2.96 (4H, m), 3.58 (4H, m), 3.81 (3H, s), 3.90 (2H, s), 6.88 (2H, d, J=8.1 Hz), 6.93 (1H, m), 7.07 (1H, s), 7.43 (1H, m), 7.50 (1H, m), 7.72 (2H, d, J=8.3 Hz), 7.92 (2H, m), 8.22 (1H, m), 8.36 (1H, s), 11.22 (1H, bs)

Mass spectrometric value (ESI-MS) 615 (M−1)

Compound 916 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-4-pyrrolidin-1-yl-phenyl]-benzamide

The title compound 916 was produced in substantially the same manner as in Example F.

¹H-NMR (CD₃OD, 400 MHz): δ 1.06 (6H, t, J=7.1 Hz), 1.99 (4H, m), 2.26 (9H, m), 2.58 (2H, m), 2.70 (4H, m), 2.82 (2H, m), 3.30 (4H, m), 3.63 (2H, s), 6.75 (1H, dd, J=9.2 Hz, J=2.8 Hz), 6.90 (1H, d, J=2.7 Hz), 7.14 (1H, d, J=7.8 Hz), 7.47 (2H, m), 7.54 (1H, d, J=7.8 Hz), 7.57 (1H, s), 7.85 (1H, d, J=7.8 Hz), 7.92 (1H, s), 8.24 (1H, d, J=9.0 Hz), 8.28 (1H, s)

Mass spectrometric value (ESI-MS) 581 (M−1)

Compound 917 N-[2-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-pyrrolidin-1-yl-phenyl]-3-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 917 was produced in substantially the same manner as in Example F.

¹H-NMR (CD₃OD, 400 MHz): δ 1.02 (6H, t, J=7.2 Hz), 1.99 (4H, m), 2.25 (3H, s), 2.57 (6H, m), 2.70 (2H, m), 3.30 (4H, m), 3.62 (2H, s), 6.74 (1H, dd, J=9.0 Hz, J=2.7 Hz), 6.89 (1H, d, J=2.7 Hz), 7.47 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.54 (1H, d, J=7.6 Hz), 7.60 (1H, d, J=8.3 Hz), 7.84 (1H, d, J=7.6 Hz), 7.93 (2H, m), 8.18 (1H, d, J=9.0 Hz), 8.23 (1H, m), 8.35 (1H, s)

Mass spectrometric value (ESI-MS) 655 (M−1)

Compound 918 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[2-(4-methoxy-benzylidene-hydrazinocarbonyl)-4-pyrrolidin-1-yl-phenyl]-benzamide

The title compound 918 was produced in substantially the same manner as in Example F.

¹H-NMR (CD₃OD, 400 MHz): δ 1.04 (6H, t, J=7.2 Hz), 2.00 (4H, m), 2.26 (3H, s), 2.52-2.68 (6H, m), 2.75 (2H, m), 3.31 (4H, m), 3.64 (2H, s), 3.81 (3H, s), 6.75 (1H, dd, J=9.0 Hz, J=2.7 Hz), 6.89 (1H, d, J=2.7 Hz), 6.93 (2H, d, J=8.8 Hz), 7.47 (1H, t, J=7.7 Hz), 7.54 (1H, d, J=7.3 Hz), 7.73 (2H, d, J=9.0 Hz), 7.85 (1H, m), 7.91 (1H, s), 8.25 (1H, d, J=9.0 Hz), 8.28 (1H, s)

Mass spectrometric value (ESI-MS) 583 (M−1)

Compound 919 N-[2-(3,4-Dimethyl-benzylidene-hydrazinocarbonyl)-4-pyrrolidin-1-yl-phenyl]-3-(2-hydroxy-ethylsulfanylmethyl)-benzamide

The title compound 919 was produced in substantially the same manner as in Example F.

¹H-NMR (CD₃OD, 400 MHz): δ 2.06 (4H, m), 2.29 (3H, s), 2.31 (3H, s), 2.57 (2H, t, J=7.0 Hz), 3.37 (4H, m), 3.68 (2H, t, J=6.8 Hz), 3.85 (2H, s), 6.81 (1H, d, J=8.1 Hz), 6.93 (1H, s), 7.02-7.23 (2H, m), 7.45-7.59 (2H, m), 7.64 (1H, s), 7.84 (1H, d, J=7.3 Hz), 7.90 (1H, s), 8.26 (2H, m)

Mass spectrometric value (ESI-MS) 529 (M−1)

Compound 920 N-[2-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-pyrrolidin-1-yl-phenyl]-3-(2-hydroxy-ethylsulfanylmethyl)-benzamide

The title compound 920 was produced in substantially the same manner as in Example F.

¹H-NMR (CD₃OD, 400 MHz): δ 2.07 (4H, m), 2.57 (2H, t, J=7.0 Hz), 3.38 (4H, m), 3.68 (2H, t, J=6.8 Hz), 3.85 (2H, s), 6.83 (1H, m), 6.94 (1H, m), 7.48 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.57 (1H, d, J=7.3 Hz), 7.67 (1H, d, J=8.3 Hz), 7.83 (1H, d, J=7.6 Hz), 7.90 (1H, s), 8.04 (1H, d, J=8.0 Hz), 8.22 (1H, d, J=9.0 Hz), 8.32 (1H, s), 8.36 (1H, s)

Mass spectrometric value (ESI-MS) 603 (M−1)

Compound 921 3-(2-Hydroxy-ethylsulfanylmethyl)-N-[2-(4-methoxy-benzylidene-hydrazinocarbonyl)-4-pyrrolidin-1-yl-phenyl]-benzamide

The title compound 921 was produced in substantially the same manner as in Example F.

¹H-NMR (CD₃OD, 400 MHz): δ 2.05 (4H, m), 2.57 (2H, t, J=7.0 Hz), 3.36 (4H, m), 3.68 (2H, t, J=6.8 Hz), 3.84 (5H, m), 6.81 (1H, d, J=8.8 Hz), 6.93 (1H, s), 6.97 (2H, d, J=9.0 Hz), 7.47 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.57 (1H, d, J=7.3 Hz), 7.77 (2H, d, J=8.8 Hz), 7.83 (1H, d, J=7.2 Hz), 7.90 (1H, s), 8.24 (1H, d, J=9.0 Hz), 8.27 (1H, s)

Mass spectrometric value (ESI-MS) 531 (M−1)

Compound 922 N-[2-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-(4-methyl-[1,4]diazepan-1-yl)-phenyl]-3-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 922 was produced in substantially the same manner as in Example F.

¹H-NMR (CDCl₃, 400 MHz): δ 1.03 (6H, t, J=7.1 Hz), 1.67 (2H, m), 2.20-2.80 (18H, m), 3.04 (2H, m), 3.11 (2H, m), 3.63 (2H, s), 6.57 (1H, d, J=8.6 Hz), 6.64 (1H, s), 7.46 (1H, m), 7.57 (2H, m), 7.78 (1H, d, J=7.8 Hz), 7.94 (1H, d, J=8.8 Hz), 8.00 (1H, s), 8.08 (1H, d, J=7.8 Hz), 8.13 (1H, s), 8.64 (1H, s), 10.87 (1H, s)

Mass spectrometric value (ESI-MS) 698, 699 (M−1)

Compound 923 N-{2-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-[4-(2-hydroxy-ethyl)-piperazin-1-yl]-phenyl}-3-(2-hydroxy-ethylsulfanylmethyl)-benzamide

The title compound 923 was produced in substantially the same manner as in Example F.

¹H-NMR (CD₃OD, 400 MHz): δ 2.57 (2H, t, J=7.0 Hz), 2.60 (2H, t, J=6.0 Hz), 2.72 (4H, m), 3.31 (4H, m), 3.68 (2H, t, J=7.0 Hz), 3.73 (2H, t, J=6.0 Hz), 3.85 (2H, s), 7.23 (1H, dd, J=9.0 Hz, J=2.7 Hz), 7.38 (1H, d, J=2.7 Hz), 7.48 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.58 (1H, d, J=7.8 Hz), 7.67 (1H, d, J=8.6 Hz), 7.84 (1H, d, J=7.6 Hz), 7.91 (1H, s), 8.02 (1H, d, J=8.6 Hz), 8.31 (1H, m), 8.37 (2H, m)

Mass spectrometric value (ESI-MS) 662 (M−1)

Compound 924 N-{2-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-[4-(2-hydroxy-ethyl)-piperazin-1-yl]-phenyl}-3-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 924 was produced in substantially the same manner as in Example F.

¹H-NMR (CD₃OD, 400 MHz): δ 1.01 (6H, t, J=7.2 Hz), 2.26 (3H, s), 2.58 (8H, m), 2.70 (6H, m), 3.32 (4H, m), 3.64 (2H, s), 3.73 (2H, t, J=5.9 Hz), 7.22 (1H, dd, J=9.0 Hz, J=2.7 Hz), 7.39 (1H, d, J=2.7 Hz), 7.49 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.57 (1H, d, J=7.6 Hz), 7.65 (1H, d, J=8.5 Hz), 7.87 (1H, m), 7.93 (1H, s), 7.99 (1H, d, J=8.3 Hz), 8.28 (1H, m), 8.36 (2H, m)

Mass spectrometric value (ESI-MS) 714 (M−1)

Compound 925 1-{3-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-[3-(2-hydroxy-ethylsulfanylmethyl)-benzoylamino]-phenyl}-piperidine-3-carboxylic acid

The title compound 925 was produced in substantially the same manner as in Example F.

¹H-NMR (DMSO-d₆, 400 MHz): δ 1.54-3.90 (15H, m), 7.24 (1H, m), 7.37 (1H, s), 7.54 (2H, m), 7.77 (1H, d, J=7.3 Hz), 7.82 (1H, d, J=8.3 Hz), 7.87 (1H, s), 8.05 (1H, d, J=8.1 Hz), 8.22 (2H, m), 8.54 (1H, s), 11.23 (1H, s), 12.34 (1H, s)

Mass spectrometric value (ESI-MS) 684 (M+23)

Compound 926 N-[2-(3,4-Dimethyl-benzylidene-hydrazinocarbonyl)-4-thiomorpholin-4-yl-phenyl]-3-(2-hydroxy-ethylsulfanylmethyl)-benzamide

The title compound 926 was produced in substantially the same manner as in Example F.

¹H-NMR (DMSO-d₆, 400 MHz): δ 2.27 (3H, s), 2.28 (3H, s), 2.73 (4H, m), 3.32-3.60 (8H, m), 3.85 (2H, s), 7.22 (2H, m), 7.31 (1H, d, J=2.9 Hz), 7.43-7.59 (4H, m), 7.77 (1H, d, J=7.1 Hz), 7.87 (1H, s), 8.30 (1H, m), 8.36 (1H, s), 11.38 (1H, s), 11.91 (1H, s)

Mass spectrometric value (ESI-MS) 561 (M−1)

Compound 927 N-[2-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-thiomorpholin-4-yl-phenyl]-3-(2-hydroxy-ethylsulfanylmethyl)-benzamide

The title compound 927 was produced in substantially the same manner as in Example F.

¹H-NMR (DMSO-d₆, 400 MHz): δ 2.72 (4H, m), 3.31 (2H, m), 3.56 (6H, m), 3.84 (2H, s), 4.79 (1H, m), 7.20 (1H, m), 7.29 (1H, m), 7.53 (2H, m), 7.77 (1H, d, J=7.6 Hz), 7.80 (1H, d, J=8.5 Hz), 7.86 (1H, s), 8.05 (1H, m), 8.21 (1H, s), 8.25 (1H, m), 8.48 (1H, s), 11.20 (1H, s), 12.21 (1H, s)

Mass spectrometric value (ESI-MS) 635 (M−1)

Compound 928 3-(2-Hydroxy-ethylsulfanylmethyl)-N-[2-(4-methoxy-benzylidene-hydrazinocarbonyl)-4-thiomorpholin-4-yl-phenyl]-benzamide

The title compound 928 was produced in substantially the same manner as in Example F.

¹H-NMR (DMSO-d₆, 400 MHz): δ 2.73 (4H, m), 3.35 (2H, m), 3.50-3.60 (6H, m), 3.82 (3H, s), 3.85 (2H, s), 7.03 (2H, d, J=8.8 Hz), 7.20 (1H, dd, J=9.1 Hz, J=2.8 Hz), 7.31 (1H, d, J=2.7 Hz), 7.54 (2H, m), 7.71 (2H, d, J=8.6 Hz), 7.77 (1H, d, J=7.3 Hz), 7.87 (1H, s), 8.31 (1H, d, J=9.3 Hz), 8.38 (1H, s), 11.42 (1H, s), 11.87 (1H, s)

Mass spectrometric value (ESI-MS) 563 (M−1)

Compound 929 N-[2-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-thiomorpholin-4-yl-phenyl]-3-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 929 was produced in substantially the same manner as in Example F.

¹H-NMR (CDCl₃, 400 MHz): δ 1.25 (6H, s), 2.28 (3H, s), 2.44 (4H, m), 2.56-2.76 (8H, m), 3.25 (4H, m), 3.65 (2H, s), 6.84 (1H, m), 7.00 (1H, s), 7.43-7.60 (3H, m), 7.88 (1H, m), 7.95-8.11 (4H, m), 8.60 (1H, s), 11.10 (1H, s)

Mass spectrometric value (ESI-MS) 687 (M−1)

Example H

Compound 930 N-[5-Bromo-3-(4-methoxy-benzylidene-hydrazinocarbonyl)-thiophen-2-yl]-3-dimethylaminomethyl-benzamide

2-Amino-thiophene-3-carboxylic acid methyl ester (compound A) (3.0 g) was dissolved in anhydrous methylene chloride (100 ml). Subsequently, pyridine (2.4 ml) and 3-(chloromethyl)benzoyl chloride (compound B) (2.8 ml) were added to the solution at 0° C., and the mixture was stirred at 0° C. for one hr. After the completion of the reaction, distilled water was added thereto, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate and was then concentrated. The residue was purified by column chromatography using a hexane-acetone system to give 2-(3-chloromethyl-benzoylamino)-thiophene-3-carboxylic acid methyl ester as a useful intermediate (4.7 g, yield 100%).

2-(3-Chloromethyl-benzoylamino)-thiophene-3-carboxylic acid methyl ester (2.0 g) produced by the above reaction was dissolved in anhydrous methylene chloride (60 ml). Triethylamine (3 ml) and dimethylamine hydrochloride (compound B′) (1.1 g) were added to the solution at room temperature, and the mixture was stirred at room temperature for 15 hr. After the completion of the reaction, water was added thereto at room temperature, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated. The residue was purified by column chromatography using a hexane-acetone system to give 2-(3-dimethylaminomethyl-benzoylamino)-thiophene-3-carboxylic acid methyl ester as a useful intermediate (1.14 g, yield 52%).

2-(3-dimethylaminomethyl-benzoylamino)-thiophene-3-carboxylic acid methyl ester (1.14 g) produced by the above reaction was dissolved in monochlorobenzene. N-bromosuccinimide (877 mg) and 2,2′-azobisisobutyronitrile (81 mg) were added to the solution, and the mixture was stirred at 90° C. for 2 hr. After the completion of the reaction, the reaction solution was concentrated, and the residue was purified by column chromatography using a hexane-acetone system to give 5-bromo-2-(3-dimethylaminomethyl-benzoylamino)-thiophene-3-carboxylic acid methyl ester as a useful intermediate (706 mg, yield 54%).

5-Bromo-2-(3-dimethylaminomethyl-benzoylamino)-thiophene-3-carboxylic acid methyl ester (706 mg) produced by the above reaction was dissolved in ethanol (10 ml). Hydrazine monohydrate (1 ml) was added to the solution, and the mixture was stirred at room temperature for 15 hr. After the completion of the reaction, water was added thereto at room temperature, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated. The residue was purified by column chromatography eluted with a chloroform-methanol system to give N-(5-bromo-3-hydrazinocarbonyl-thiophen-2-yl)-3-dimethylaminomethyl-benzamide as a hydrazine compound (448 mg, yield 64%).

N-(5-bromo-3-hydrazinocarbonyl-thiophen-2-yl)-3-dimethylamino-methyl-benzamide (50 mg) as the hydrazine compound produced by the above reaction was dissolved in anhydrous toluene (1.0 ml). p-Methoxybenzaldehyde (compound C) (60 μl) was added to the solution at room temperature, and the mixture was stirred at room temperature for 15 hr. After the completion of the reaction, the reaction product was purified by column chromatography eluted with a chloroform-methanol system to give the title compound 930 (29 mg, yield 45%).

¹H-NMR (CDCl₃, 400 MHz): δ 2.22 (6H, s), 3.67 (2H, s), 3.78 (3H, s), 6.84 (2H, m), 7.42 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.54-7.61 (3H, m), 7.89 (1H, d, J=7.6 Hz), 7.93 (1H, s), 8.22 (1H, s), 9.87 (1H, bs), 12.93 (1H, bs)

Mass spectrometric value (ESI-MS) 515 (M−1)

Compound 931 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[2-(4-methoxy-benzylidene-hydrazinocarbonyl)-4-(4-methyl-[1,4]diazepan-1-yl)-phenyl]-benzamide

The title compound 931 was produced in substantially the same manner as in Example F.

¹H-NMR (CDCl₃, 400 MHz): δ 1.03 (6H, t, J=7.2 Hz), 1.73 (2H, m), 2.24 (5H, m), 2.37 (2H, m), 2.44-2.60 (9H, m), 2.65 (2H, m), 3.12 (2H, m), 3.20 (2H, m), 3.61 (2H, s), 3.84 (3H, s), 6.62 (1H, m), 6.69-6.78 (2H, m), 6.92 (2H, d, J=8.5 Hz), 7.41 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.52 (1H, d, J=7.6 Hz), 7.80 (2H, d, J=8.1 Hz), 7.96 (1H, s), 8.08 (1H, d, J=9.0 Hz), 8.49 (1H, s), 11.01 (1H, s)

Mass spectrometric value (ESI-MS) 626 (M−1)

Compound 932 3-[(4-Chloro-3-trifluoromethyl-benzylidene)-amino]-2-[3-(2-hydroxy-ethylsulfanylmethyl)-phenyl]-6-(4-methyl-[1,4]diazepan-1-yl)-3 H-quinazolin-4-one

The title compound 932 was produced in substantially the same manner as in Example F. ¹H-NMR (CDCl₃, 400 MHz): δ 2.10 (2H, m), 2.42 (3H, s), 2.55-2.68 (4H, m), 2.80 (2H, m), 3.58-3.84 (8H, m), 7.23 (1H, m), 7.34-7.44 (3H, m), 7.54 (2H, m), 7.68 (2H, m), 7.76 (1H, m), 7.95 (1H, d, J=1.7 Hz), 9.36 (1H, s)

Mass spectrometric value (ESI-MS) 652 (M+23)

Compound 933 2-(3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-phenyl)-3-[(4-methoxy-benzylidene)-amino]-6-(4-methyl-[1,4]diazepan-1-yl)-3H-quinazolin-4-one

The title compound 933 was produced in substantially the same manner as in Example F.

¹H-NMR (CDCl₃, 400 MHz): δ 0.99 (6H, t, J=7.2 Hz), 2.06 (2H, m), 2.11 (3H, s), 2.39 (3H, s), 2.45-2.60 (10H, m), 2.76 (2H, m), 3.51 (2H, s), 3.62 (2H, t, J=6.3 Hz), 3.70 (2H, m), 3.84 (3H, s), 6.90 (2H, d, J=8.8 Hz), 7.22 (1H, dd, J=9.0 Hz, J=3.2 Hz), 7.35 (1H, m), 7.44 (1H, d, J=3.2 Hz), 7.57 (1H, m), 7.60-7.70 (4H, m), 8.88 (1H, s)

Mass spectrometric value (ESI-MS) 632 (M+23)

Compound 934 1-{3-(3,4-Dimethyl-benzylidene-hydrazinocarbonyl)-4-[3-(2-hydroxy-ethylsulfanylmethyl)-benzoylamino]-phenyl}-piperidine-3-carboxylic acid

The title compound 934 was produced in substantially the same manner as in Example F.

¹H-NMR (DMSO-d₆, 400 MHz): δ 1.50-3.88 (21H, m), 7.14-7.60 (7H, m), 7.77 (1H, d, J=7.3 Hz), 7.87 (1H, s), 8.32 (1H, d, J=9.0 Hz), 8.40 (1H, s), 11.44 (1H, s), 12.01 (1H, s)

Mass spectrometric value (ESI-MS) 609 (M+23)

Example I

Compound 935 N-[2-(3,4-Dimethyl-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-3,4-dimethoxy-benzamide

5-Chloro-2-nitro-benzoic acid (compound A′) (10.0 g) was dissolved in ethanol (100 ml). Thionyl chloride (20 ml) was added dropwise to the solution at 0° C., and the mixture was then heated under reflux with stirring for 48 hr. After the completion of the reaction, the reaction solution was concentrated under the reduced pressure. Distilled water was added to the residue, and the mixture was neutralized with a saturated aqueous sodium hydrogencarbonate solution under ice cooling. The cooled solution was subjected to separatory extraction with ethyl acetate. The organic layer was dried over sodium sulfate and was then concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a chloroform-methanol system to give 5-chloro-2-nitro-benzoic acid ethyl ester as a useful intermediate (11.0 g, yield 97%).

5-Chloro-2-nitro-benzoic acid ethyl ester (3.1 g) produced by the above production process was dissolved in N,N-dimethylformamide (30 ml). Potassium carbonate (3.8 g) and piperidine (compound D) (2.8 ml) were added to the solution at room temperature, and the mixture was then heated under reflux with stirring for 12 hr. After the completion of the reaction, distilled water was added thereto at room temperature, and the mixture was subjected to separatory extraction with ethyl acetate. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure to give crude 2-nitro-5-piperidin-1-yl-benzoic acid ethyl ester (3.81 g, crude yield 100%).

Subsequently, the crude 2-nitro-5-piperidin-1-yl-benzoic acid ethyl ester (3.8 g) was dissolved in methanol (35 ml). Platinum oxide (300 mg) was added to the solution at room temperature, the air in the reaction system was replaced by hydrogen, and the mixture was then stirred for 12 hr. After the completion of the reaction, the atmosphere in the reaction system was replaced by nitrogen, and the reaction solution was then filtered through Celite to remove platinum oxide and was then concentrated under the reduced pressure to give crude 2-amino-5-piperidin-1-yl-benzoic acid ethyl ester (compound A) as a useful intermediate (3.4 g, crude yield 100%).

Subsequently, crude 2-amino-5-piperidin-1-yl-benzoic acid ethyl ester (compound A) (1.3 g) was dissolved in anhydrous methylene chloride (100 ml). Triethylamine (5.6 ml) and 3,4-dimethoxy-benzoyl chloride (compound B) (1.8 g) were added at 0° C., and the mixture was stirred at room temperature for 24 hr. After the completion of the reaction, distilled water was added thereto at room temperature, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a hexane-chloroform system to give 2-(3,4-dimethoxy-benzoylamino)-5-piperidin-1-yl-benzoic acid ethyl ester (960 mg, yield 52%).

2-(3,4-Dimethoxy-benzoylamino)-5-piperidin-1-yl-benzoic acid ethyl ester (380 mg) produced by the above process was dissolved in ethanol (10 ml). Hydrazine monohydrate (3 ml) was added dropwise to the solution at room temperature, and the mixture was stirred at 90° C. for 1.5 hr. After the completion of the reaction, the reaction solution was allowed to stand for cooling, and the precipitated crystals were filtered through Kiriyama Rohto to give N-(2-hydrazinocarbonyl-4-piperidin-1-yl-phenyl)-3,4-dimethoxy-benzamide as a useful intermediate (270 mg, yield 71%).

Subsequently, N-(2-hydrazinocarbonyl-4-piperidin-1-yl-phenyl)-3,4-dimethoxy-benzamide (56 mg) produced by the above process was dissolved in anhydrous toluene (5 ml). 3,4-Dimethylbenzaldehyde (compound C) (40 mg) and a catalytic amount of acetic acid were added dropwise to the solution at room temperature, and the mixture was stirred at 90° C. for 16 hr. After the completion of the reaction, distilled water was added thereto at room temperature, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a chloroform-methanol system to give the title compound 935 (74 mg, yield 96%).

¹H-NMR (CD₃OD, 400 MHz): δ 8.32 (1H, d, J=9.2 Hz), 8.28 (1H, s), 7.63 (1H, s), 7.59 (1H, dd, J=2.2 Hz, J=8.3 Hz), 7.54 (1H, d, J=1.9 Hz), 7.52 (1H, d, J=7.8 Hz), 7.36 (1H, d, J=2.7 Hz), 7.17-7.24 (2H, m), 7.06 (1H, d, J=8.6 Hz), 3.92 (3H, s), 3.90 (3H, s), 3.20-3.25 (4H, m), 2.30 (3H, s), 2.29 (3H, s), 1.70-1.80 (4H, m), 1.57-1.66 (2H, m)

Mass spectrometric value (ESI-MS) 513, 514 (M−1) 537, 538 (M+23)

Compound 936 3,4-Dimethoxy-N-[4-piperidin-1-yl-2-(pyridin-3-ylmethylene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 936 was produced in substantially the same manner as in Example I.

¹H-NMR (CD₃OD, 400 MHz): δ 8.89 (1H, s), 8.55-8.60 (1H, m), 8.39 (1H, s), 8.34-8.39 (1H, m), 8.28 (1H, d, J=9.0 Hz), 7.48-7.61 (3H, m), 7.37 (1H, d, J=2.9 Hz), 7.22 (1H, dd, J=2.9 Hz, J=9.3 Hz), 7.06 (1H, d, J=8.3 Hz), 3.91 (3H, s), 3.90 (3H, s), 3.20-3.25 (4H, m), 1.70-1.80 (4H, m), 1.57-1.66 (2H, m)

Mass spectrometric value (ESI-MS) 486 (M−1)

Compound 937 N-[2-(1H-Imidazol-2-ylmethylene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-3,4-dimethoxy-benzamide

The title compound 937 was produced in substantially the same manner as in Example I.

¹H-NMR (CD₃OD, 400 MHz): δ 8.34 (1H, d, J=9.0 Hz), 7.03-7.62 (8H, m), 3.93 (3H, s), 3.90 (3H, s), 3.15-3.19 (4H, m), 1.55-1.84 (6H, m)

Mass spectrometric value (ESI-MS) 475 (M−1)

Compound 938 N-[2-(4-Hydroxy-3-methoxy-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-3,4-dimethoxy-benzamide

The title compound 938 was produced in substantially the same manner as in Example I.

¹H-NMR (CD₃OD, 400 MHz): δ 8.32 (1H, d, J=9.3 Hz), 8.24 (1H, s), 7.71 (1H, d, J=1.7 Hz), 7.59 (1H, dd, J=1.9 Hz, J=8.3 Hz), 7.56 (1H, d, J=2.0 Hz), 7.36 (1H, d, J=2.9 Hz), 7.22 (1H, dd, J=2.9 Hz, J=9.3 Hz), 7.05-7.11 (2H, m), 6.82 (1H, d, J=8.0 Hz), 3.94 (3H, s), 3.92 (3H, s), 3.90 (3H, s), 3.21-3.25 (4H, m), 1.71-1.80 (4H, m), 1.58-1.67 (2H, m)

Mass spectrometric value (ESI-MS) 529, 531, 532 (M−1) 555 (M+23)

Compound 939 N-[2-(3,4-Dimethyl-benzylidene-hydrazinocarbonyl)-4-morpholin-4-yl-phenyl]-3,4-dimethoxy-benzamide

The title compound 939 was produced in substantially the same manner as in Example I.

¹H-NMR (CD₃OD, 400 MHz): δ 8.37 (1H, d, J=9.3 Hz), 8.28 (1H, s), 7.65 (1H, s), 7.60 (1H, dd, J=2.2 Hz, J=8.3 Hz), 7.56 (1H, d, J=2.2 Hz), 7.50-7.55 (1H, m), 7.37 (1H, d, J=2.7 Hz), 7.21-7.26 (1H, m), 7.20 (1H, d, J=7.8 Hz), 7.08 (1H, d, J=8.3 Hz), 3.92 (3H, s), 3.91 (3H, s), 3.85-3.89 (4H, m), 3.20-3.29 (4H, m), 2.32 (3H, s), 2.30 (3H, s)

Mass spectrometric value (ESI-MS) 515 (M−1)

Compound 940 N-[2-(4-Hydroxy-3-methoxy-benzylidene-hydrazinocarbonyl)-4-morpholin-4-yl-phenyl]-3,4-dimethoxy-benzamide

The title compound 940 was produced in substantially the same manner as in Example I.

¹H-NMR (CDCL₃, 400 MHz): δ 11.6 (1H, bs), 8.27-8.40 (2H, m), 7.55-7.62 (2H, m), 7.47-7.53 (1H, m), 7.40-7.44 (1H, m), 6.88-7.16 (4H, m), 3.98 (3H, s), 3.97 (3H, s), 3.94 (3H, s), 3.60-3.72 (4H, m), 2.97-3.05 (4H, m)

Mass spectrometric value (ESI-MS) 533, 534, 535 (M−1) 1067 (2M-1)

Compound 941 3,4-Dimethoxy-N-[2-(4-methoxy-benzylidene-hydrazinocarbonyl)-4-morpholin-4-yl-phenyl]-benzamide

The title compound 941 was produced in substantially the same manner as in Example I.

¹H-NMR (CD₃OD, 400 MHz): δ 8.28-8.32 (1H, m), 7.83-7.89 (1H, m), 7.73-7.82 (2H, m), 7.53-7.66 (3H, m), 7.20-7.30 (1H, m), 7.05-7.12 (1H, m), 6.96-7.04 (2H, m), 3.83-3.95 (13H, m), 3.29-3.35 (4H, m)

Mass spectrometric value (ESI-MS) 519, 520 (M+1)

Example J

Compound 942 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-benzamide

5-Chloro-2-nitro-benzoic acid (compound A′) (10.0 g) was dissolved in ethanol (100 ml). Thionyl chloride (20 ml) was added dropwise to the solution at 0° C., and the mixture was then heated under reflux with stirring for 48 hr. After the completion of the reaction, the reaction solution was concentrated under the reduced pressure. Distilled water was added to the residue, and the mixture was neutralized with a saturated aqueous sodium hydrogencarbonate solution under ice cooling, and was then subjected to separatory extraction with ethyl acetate. The organic layer was dried over sodium sulfate and was then concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a chloroform-methanol system to give 5-chloro-2-nitro-benzoic acid ethyl ester as a useful intermediate (11.0 g, yield 97%).

5-Chloro-2-nitro-benzoic acid ethyl ester (3.1 g) produced by the above process was dissolved in N,N-dimethylformamide (30 ml), potassium carbonate (3.8 g) and piperidine (compound D) (2.8 ml) were added to the solution at room temperature, and was then heated under reflux with stirring for 12 hr. After the completion of the reaction, distilled water was added thereto at room temperature, and the mixture was subjected to separatory extraction with ethyl acetate. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure to give crude 2-nitro-5-piperidin-1-yl-benzoic acid ethyl ester (3.8 g, crude yield 100%).

Subsequently, crude 2-nitro-5-piperidin-1-yl-benzoic acid ethyl ester (3.8 g) was dissolved in methanol (35 ml), and platinum oxide (300 mg) was added to the solution at room temperature. The air in the reaction system was replaced by hydrogen, and the mixture was then stirred for 12 hr. After the completion of the reaction, the atmosphere in the reaction system was replaced by nitrogen, and the reaction solution was then filtered through Celite to remove platinum oxide, and was then concentrated under the reduced pressure to give crude 2-amino-5-piperidin-1-yl-benzoic acid ethyl ester (compound A) as a useful intermediate (3.4 g, crude yield 100%).

2-Amino-5-piperidin-1-yl-benzoic acid ethyl ester (compound A) (1.6 g) synthesized by the above process was dissolved in anhydrous methylene chloride (20 ml). Pyridine (1.0 ml) and 3-(chloromethyl)benzoyl chloride (compound B) (1.2 ml) were added dropwise to the solution at 0° C., and the mixture was then stirred at room temperature for one hr. After the completion of the reaction, the reaction solution was concentrated under the reduced pressure. Distilled water was added to the residue, and the mixture was subjected to separatory extraction with ethyl acetate. The organic layer was dried over sodium sulfate and was then concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a chloroform-methanol system to give 2-(3-chloromethyl-benzoylamino)-5-piperidin-1-yl-benzoic acid ethyl ester as a useful intermediate (1.7 g, yield 63%).

2-(3-Chloromethyl-benzoylamino)-5-piperidin-1-yl-benzoic acid ethyl ester (200 mg) produced by the above reaction was dissolved in anhydrous methylene chloride (2 ml). Triethylamine (150 μl) and diisopropanolamine (compound B′) (150 mg) were added to the solution at room temperature, and the mixture was then stirred at that temperature for 36 hr. After the completion of the reaction, distilled water was added thereto at room temperature, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a chloroform-methanol system to give 2-(3-{[bis-(2-hydroxy-propyl)-amino]-methyl}-benzoylamino)-5-piperidin-1-yl-benzoic acid ethyl ester as a useful intermediate (200 mg, yield 82%).

Subsequently, 2-(3-{[bis-(2-hydroxy-propyl)amino]-methyl}-benzoylamino)-5-piperidin-1-yl-benzoic acid ethyl ester (200 mg) was dissolved in ethanol (2 ml). Hydrazine monohydrate (200 μl) was added dropwise to the solution at room temperature, and the mixture was then stirred at that temperature for 12 hr. After the completion of the reaction, the reaction solution was concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a chloroform-methanol system to give 3-{[bis-(2-hydroxy-propyl)-amino]-methyl}-N-(2-hydrazinocarbonyl-4-piperidin-1-yl-phenyl)benzamide as a useful intermediate (200 mg, yield 100%).

3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-(2-hydrazino-carbonyl-4-piperidin-1-ylphenyl)benzamide (53 mg) produced by the above process was dissolved in anhydrous toluene (5 ml). 4-Chloro-3-(trifluoromethyl)benzaldehyde (compound C) (69 mg) and a catalytic amount of acetic acid were added dropwise to the solution at room temperature, and the mixture was then stirred at 90° C. for 3 hr. After the completion of the reaction, the reaction solution was allowed to stand for cooling, and the resultant crystals were collected by Kiriyama Rohto to give the title compound 942 (15 mg, yield 20%). The filtrate obtained by the filtration through Kiriyama Rohto was concentrated under the reduced pressure, and the residue was purified by column chromatography eluted with a chloroform-methanol system to again give the title compound 942 (37 mg, yield 50%) (final step: total yield 70%).

¹H-NMR (CD₃OD, 400 MHz): δ 8.31-8.38 (3H, m), 8.00-8.07 (2H, m), 7.86 (1H, d, J=8.0 Hz), 7.67 (1H, d, J=8.6 Hz), 7.58 (1H, d, J=7.8 Hz), 7.48 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.38 (1H, d, J=2.7 Hz), 7.23 (1H, dd, J=2.7 Hz, J=9.0 Hz), 3.83-3.95 (4H, m), 3.20-3.25 (4H, m), 2.38-2.55 (4H, m), 1.70-1.78 (4H, m), 1.58-1.66 (2H, m), 1.07 (3H, s), 1.06 (3H, s)

Mass spectrometric value (ESI-MS) 672, 674 (M−1)

Example K

Compound 943 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[4-(2-diethylamino-ethoxy)-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-4-hydroxyphenyl]-benzamide (45 mg) produced in substantially the same manner as in Example 8 was dissolved in N,N-dimethylformamide (10 ml). 60% Sodium hydride (4.0 mg) was added to the solution at room temperature, and the mixture was stirred at that temperature for 10 min. Subsequently, (2-bromoethyl)diethylamine hydrobromide (44 mg) was added thereto, and the mixture was stirred for 12 hr. After the completion of the reaction, distilled water was added thereto, and the mixture was subjected to separatory extraction with ethyl acetate. The organic layer was washed with saturated brine and was dried over sodium sulfate. The organic layer was concentrated under the reduced pressure, and the residue was purified by column chromatography eluted with a chloroform system to give the title compound 943 (7 mg, yield 13%).

¹H-NMR (CDCL₃, 400 MHz): δ 10.02 (1H, bs), 8.20-8.25 (1H, m), 7.75-8.00 (3H, m), 7.35-7.50 (2H, m), 7.30 (1H, s), 7.23 (1H, s), 6.96-7.10 (3H, m), 4.25-4.45 (2H, m), 3.70-4.00 (4H, m), 2.30-2.80 (10H, m), 2.20-2.30 (6H, m), 1.00-1.20 (12H, m)

Mass spectrometric value (ESI-MS) 630 (M−1) 654 (M+23)

Example L

Compound 944 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-4-(2-oxo-pyrrolidin-1-yl)-phenyl]-benzamide

5-Amino-2-nitro-benzoic acid (compound A′) (910 mg) was dissolved in methanol (50 ml). Thionyl chloride (0.74 ml) was added dropwise to the solution on an ice bath, and a reaction was allowed to proceed under reflux with heating for 12 hr. After the completion of the reaction, the reaction solution was allowed to stand for cooling to room temperature and was then concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a chloroform-methanol system to give 5-amino-2-nitro-benzoic acid methyl ester (410 mg, yield 42%).

Subsequently, 5-amino-2-nitro-benzoic acid methyl ester (750 mg) was dissolved in anhydrous methylene chloride (30 ml). Pyridine (360 mg: dissolved in 2 ml of anhydrous methylene chloride) and 4-chloro-butyryl chloride (compound D) (630 mg: dissolved in 2 ml of anhydrous methylene chloride) were added dropwise at room temperature, and the mixture was then stirred at that temperature for 12 hr. After the completion of the reaction, distilled water was added thereto at room temperature, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a chloroform-methanol system to give 5-(4-chloro-butyrylamino)-2-nitro-benzoic acid methyl ester as a useful intermediate (1.2 g, yield 100%).

Subsequently, 5-(4-chloro-butyrylamino)-2-nitro-benzoic acid methyl ester (50 mg) was dissolved in N,N-dimethylformamide (5 ml). Morpholine (70 mg) and potassium carbonate (44 mg) were added to the solution at room temperature, and the mixture was stirred at room temperature for 3 hr. After the completion of the reaction, distilled water was added thereto at room temperature, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a chloroform-methanol system to give 2-nitro-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester (45 mg, yield 100%).

2-Nitro-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester (24 mg) was dissolved in ethanol (5 ml), and 10% palladium-carbon (3 mg) was added to the solution at room temperature. The air in the reaction system was replaced by hydrogen, and the reaction solution was then stirred at that temperature for 4 hr. After the completion of the reaction, the reaction solution was filtered through Celite to remove 10% palladium-carbon and was then concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a chloroform-methanol system to give 2-amino-5-(2-oxo-pyrrolidin-1-yl)benzoic acid methyl ester (compound A) (10 mg, yield 83%).

2-Amino-5-(2-oxo-pyrrolidin-1-yl)benzoic acid methyl ester (compound A) (10 mg) produced by the above process was dissolved in anhydrous methylene chloride. Pyridine (5 mg: dissolved in 1 ml of anhydrous methylene chloride) and 3-(chloromethyl)benzoyl chloride (compound B) (11 mg: dissolved in 1 ml of anhydrous methylene chloride) were added dropwise to the solution at 0° C., and the mixture was stirred at room temperature for 12 hr. After the completion of the reaction, distilled water was added thereto at room temperature, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a chloroform-methanol system to give 2-(3-chloromethyl-benzoylamino)-5-(2-oxo-pyrrolidin-1-yl)benzoic acid methyl ester (14 mg, yield 93%).

Subsequently, 2-(3-chloromethyl-benzoylamino)-5-(2-oxo-pyrrolidin-1-yl)benzoic acid methyl ester (14 mg) was dissolved in anhydrous methylene chloride (5 ml). Triethylamine (7 mg: dissolved in 2 ml of anhydrous methylene chloride) and diisopropanolamine (compound B′) (10 mg: dissolved in 2 ml of anhydrous methylene chloride) were added dropwise to the solution at 0° C., and the mixture was stirred at room temperature for 24 hr. After the completion of the reaction, distilled water was added thereto at room temperature, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a chloroform-methanol system to give 2-(3-{[bis-(2-hydroxy-propyl)-amino]-methyl}-benzoylamino)-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester (8.0 mg, yield 47%).

2-(3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-benzoylamino)-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester (8.0 mg) produced by the above reaction was dissolved in ethanol (5 ml). Hydrazine monohydrate (1 ml) was added dropwise to the solution at room temperature, and the mixture was stirred at that temperature for one hr. After the completion of the reaction, the reaction solution was concentrated under the reduced pressure, and the residue was purified by column chromatography eluted with a chloroform-methanol system to give 3-{[bis-(2-hydroxy-propyl)-amino]-methyl}-N-[2-hydrazinocarbonyl-4-(2-oxo-pyrrolidin-1-yl)-phenyl]-benzamide (8.0 mg, yield 100%).

Subsequently, 3-{[bis-(2-hydroxy-propyl)-amino]-methyl}-N-[2-hydrazinocarbonyl-4-(2-oxo-pyrrolidin-1-yl)-phenyl]-benzamide (8.0 mg) produced by the above reaction was dissolved in anhydrous toluene (5 ml). 3,4-Dimethylbenzaldehyde (compound C) (4.6 mg: dissolved in 2 ml of anhydrous toluene) and a catalytic amount of acetic acid were added dropwise to the solution at room temperature, and the mixture was stirred at that temperature for 4 hr. After the completion of the reaction, the reaction solution was neutralized with a saturated aqueous sodium hydrogencarbonate solution, and was then subjected to separatory extraction with ethyl acetate. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a chloroform-methanol system to give the title compound 944 (6.5 mg, yield 65%).

¹H-NMR (CDCL₃, 400 MHz): δ 12.11 (1H, d, J=8.3 Hz), 10.88 (1H, d, J=9.8 Hz), 8.74 (1H, dd, J=17.1 Hz, J=9.0 Hz), 8.20-8.30 (3H, m), 7.95-8.05 (1H, m), 7.28-7.60 (5H, m), 7.08 (1H, dd, J=3.4 Hz, J=8.0 Hz), 3.75-4.10 (5H, m), 2.40-2.61 (5H, m), 2.25 (3H, s), 2.23 (3H, s), 1.95-2.15 (2H, m), 1.25 (2H, s), 1.11 (6H, d, J=6.4 Hz)

Mass spectrometric value (ESI-MS) 598 (M−1) 622 (M+23)

Compound 945 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-(2-oxo-pyrrolidin-1-yl)-phenyl]-benzamide

The title compound 945 was produced in substantially the same manner as in Example L.

¹H-NMR (CDCL₃, 400 MHz): δ 12.33 (1H, d, J=9.0 Hz,), 11.94 (1H, bs), 8.71 (1H, dd, J=9.0 Hz, J=9.0 Hz), 8.07-8.40 (3H, m), 8.11 (1H, d, J=21.0 Hz), 7.99 (1H, d, J=7.3 Hz), 7.78 (1H, dd, J=8.3 Hz, J=29.0 Hz), 7.20-7.50 (4H, m), 3.55-4.20 (6H, m), 2.45-2.74 (4H, m), 2.25-2.42 (2H, m), 1.78-1.87 (2H, m), 1.50-1.72 (6H, m)

Mass spectrometric value (ESI-MS) 672 (M−1)

Compound 946 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[2-(4-methoxy-benzylidene-hydrazinocarbonyl)-4-(2-oxo-pyrrolidin-1-yl)-phenyl]-benzamide

The title compound 946 was produced in substantially the same manner as in Example L.

¹H-NMR (CDCL₃, 400 MHz): δ 12.17 (1H, d, J=8.8 Hz), 12.23 (1H, d, J=12.4 Hz), 8.70 (1H, dd, J=9.3 Hz, J=20.7 Hz), 8.14-8.27 (3H, m), 7.95-8.01 (1H, m), 7.68-7.74 (2H, m), 7.26-7.46 (3H, m), 6.78-6.82 (2H, m), 3.50-4.20 (9H, m), 2.35-2.63 (6H, m), 1.92-2.05 (2H, m), 1.00-1.30 (6H, m)

Mass spectrometric value (ESI-MS) 600 (M−1)

Compound 947 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[2-(4-fluoro-benzylidene-hydrazinocarbonyl)-4-(2-oxo-pyrrolidin-1-yl)-phenyl]-benzamide

The title compound 947 was produced in substantially the same manner as in Example L.

¹H-NMR (CDCL₃, 400 MHz): δ 12.21 (1H, d, J=5.4 Hz), 11.44 (1H, d, J=12.4 Hz), 8.70 (1H, dd, J=9.0 Hz, J=26.1 Hz), 8.20-8.35 (3H, m), 7.96-7.99 (1H, m), 7.72-7.82 (2H, m), 7.38-7.46 (2H, m), 7.25-7.32 (1H, m), 6.93-6.99 (2H, m), 3.50-4.10 (6H, m), 2.35-2.64 (6H, m), 1.87-1.97 (2H, m), 1.07-1.14 (6H, m)

Mass spectrometric value (ESI-MS) 588 (M−1)

Compound 948 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[2-(4-methyl-benzylidene-hydrazinocarbonyl)-4-(2-oxo-pyrrolidin-1-yl)-phenyl]-benzamide

The title compound 948 was produced in substantially the same manner as in Example L.

¹H-NMR (CDCL₃, 400 MHz): δ 12.13 (1H, d, J=3.0 Hz), 11.28 (1H, d, J=11.4 Hz), 8.68 (1H, dd, J=9.2 Hz, J=20.5 Hz), 8.16-8.29 (3H, m), 7.94-8.00 (1H, m), 7.60-7.70 (2H, m), 7.25-7.45 (3H, m), 7.06-7.11 (2H, m), 3.52-4.07 (6H, m), 2.20-2.61 (9H, m), 1.90-2.00 (2H, m), 1.09-1.30 (6H, m)

Mass spectrometric value (ESI-MS) 584 (M−1)

Example M

Compound 949 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-4-(2-hydroxy-3-piperidin-1-yl-propoxy)-phenyl]-benzamide

2-Amino-5-hydroxy-benzoic acid methyl ester (compound A) (350 mg) was dissolved in anhydrous methylene chloride (20 ml). Pyridine (230 mg) and 3-(chloromethyl)benzoic acid (compound B) (540 mg) were added dropwise to the solution at 0° C., and the mixture was stirred at room temperature for 10 min. After the completion of the reaction, distilled water was added thereto at room temperature, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a chloroform-methanol system to give 2-(3-chloromethyl-benzoylamino)-5-hydroxy-benzoic acid methyl ester as a useful intermediate (280 mg, yield 42%).

Subsequently, 2-(3-chloromethyl-benzoylamino)-5-hydroxy-benzoic acid methyl ester (280 mg) produced by the above reaction was dissolved in anhydrous methylene chloride (20 ml). Triethylamine (180 mg) and diisopropanolamine (compound B′) (230 mg) were added dropwise to the solution at room temperature, and the mixture was stirred at that temperature for 12 hr. After the completion of the reaction, distilled water was added thereto at room temperature, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a chloroform-methanol system to give 2-(3-{[bis-(2-hydroxy-propyl)-amino]-methyl}-benzoylamino)-5-hydroxy-benzoic acid methyl ester (58 mg, yield 16%).

2-(3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-benzoylamino)-5-hydroxy-benzoic acid methyl ester (60 mg) produced by the above process was dissolved in N,N-dimethylformamide (5 ml). Potassium carbonate (58 mg) and epibromohydrin (58 mg: dissolved in 2 ml of N,N-dimethylformamide) were added to the solution at room temperature, and the mixture was stirred at that temperature for 12 hr. After the completion of the reaction, distilled water was added thereto at room temperature, and the mixture was subjected to separatory extraction with ethyl acetate. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a chloroform-methanol system to give 2-(3-{[bis-(2-hydroxy-propyl)-amino]-methyl}-benzoylamino)-5-oxilanylmethoxy-benzoic acid methyl ester as a useful intermediate (68 mg, yield 66%).

2-(3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-benzoylamino)-5-oxilanylmethoxy-benzoic acid methyl ester (12 mg) produced by the above process was dissolved in anhydrous methylene chloride (5 ml). Piperidine (6.5 mg: dissolved in 1 ml of anhydrous methylene chloride) and a catalytic amount of ytterbium (III) trifluoromethanesulfonate were added to the solution at room temperature, and the mixture was stirred at that temperature for 12 hr. After the completion of the reaction, distilled water was added thereto at room temperature, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a chloroform-methanol system to give 2-(3-{[bis-(2-hydroxy-propyl)amino]methyl}benzoylamino)-5-(2-hydroxy-3-piperidin-1-yl-propoxy)-benzoic acid methyl ester (10 mg, yield 71%).

Subsequently, 2-(3-{[bis-(2-hydroxy-propyl)-amino]-methyl}-benzoylamino)-5-(2-hydroxy-3-piperidin-1-yl-propoxy)-benzoic acid methyl ester (13 mg) produced by the above process was dissolved in ethanol (5 ml). Hydrazine monohydrate (1 ml) was added dropwise to the solution at room temperature, and the mixture was stirred at that temperature for 12 hr. After the completion of the reaction, the reaction solution was concentrated under the reduced pressure, and the residue was purified by column chromatography eluted with a chloroform-methanol system to give 3-{[bis-(2-hydroxy-propyl)-amino]-methyl}-N-[2-hydrazinocarbonyl-4-(2-hydroxy-3-piperidin-1-yl-propoxy)-phenyl]-benzamide (5.8 mg, yield 45%).

3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[2-hydrazinocarbonyl-4-(2-hydroxy-3-piperidin-1-yl-propoxy)-phenyl]-benzamide (5.8 mg) produced by the above process was dissolved in anhydrous toluene (5 ml). 3,4-Dimethylbenzaldehyde (compound C) (3 mg: dissolved in 1 ml of anhydrous toluene) and a catalytic amount of acetic acid were added dropwise to the solution at room temperature, and the mixture was stirred at that temperature for 6 hr. After the completion of the reaction, the reaction solution was neutralized with a saturated aqueous sodium hydrogencarbonate solution, and was then subjected to separatory extraction with ethyl acetate. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a chloroform-methanol system to give the title compound 949 (4.0 mg, yield 60%).

¹H-NMR (CDCL₃, 400 MHz): δ 11.97 (1H, bs), 7.94-8.65 (4H, m), 6.98-7.65 (7H, m), 3.52-4.45 (7H, m), 1.50-2.90 (16H, m), 1.20-1.30 (6H, m), 1.00-1.18 (6H, m)

Mass spectrometric value (ESI-MS) 672 (M−1)

Compound 950 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-(2-hydroxy-3-piperidin-1-yl-propoxy)-phenyl]-benzamide

The title compound 950 was produced in substantially the same manner as in Example M.

¹H-NMR (CDCL₃, 400 MHz): δ 12.10-12.20 (1H, m), 7.20-8.70 (10H, m), 6.95-7.05 (1H, m), 1.50-4.25 (17H, m), 1.20-1.30 (6H, m), 0.85-1.18 (6H, m)

Mass spectrometric value (ESI-MS) 746 (M−1)

Compound 951 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[4-(3-diethylamino-2-hydroxy-propoxy)-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 951 was produced in substantially the same manner as in Example M.

¹H-NMR (CDCL₃, 400 MHz): δ 12.02 (1H, bs), 8.58-8.65 (1H, m), 8.47 (1H, s), 8.17-8.24 (1H, m), 7.80-8.00 (1H, m), 7.27-7.60 (5H, m), 6.98-7.10 (2H, m), 1.50-4.12 (23H, m), 1.20-1.28 (6H, m), 1.08-1.16 (6H, m)

Mass spectrometric value (ESI-MS) 660 (M−1)

Compound 952 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-(3-diethylamino-2-hydroxy-propoxy)-phenyl]-benzamide

The title compound 952 was produced in substantially the same manner as in Example M.

¹H-NMR (CDCL₃, 400 MHz): δ 12.21 (1H, d, J=16.1 Hz), 8.64-8.67 (1H, m), 8.50-8.58 (1H, m), 8.30-8.38 (1H, m), 7.80-8.12 (3H, m), 7.35-7.50 (4H, m), 6.97-7.00 (1H, m), 1.50-4.50 (17H, m), 1.20-1.35 (6H, m), 1.08-1.17 (6H, m)

Mass spectrometric value (ESI-MS) 734 (M−1)

Compound 953 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-4-(2-hydroxy-3-morpholin-4-yl-propoxy)-phenyl]-benzamide

The title compound 953 was produced in substantially the same manner as in Example M.

Mass spectrometric value (ESI-MS) 674 (M−1)

Compound 954 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-(2-hydroxy-3-morpholin-4-yl-propoxy)-phenyl]-benzamide

The title compound 954 was produced in substantially the same manner as in Example M.

Mass spectrometric value (ESI-MS) 748 (M−1)

Example N

Compound 955 N-[3-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-5-methyl-thiophen-2-yl]-3,4-dimethoxy-benzamide

Methyl 2-aminothiophene-3-carboxylate (compound A) (160 mg) was dissolved in anhydrous methylene chloride (5 ml). Pyridine (120 mg: dissolved in 2 ml of anhydrous methylene chloride) and 3,4-dimethoxybenzoyl chloride (compound B) (300 mg) were added to the solution at 0° C., and the mixture was stirred at room temperature for 12 hr. After the completion of the reaction, distilled water was added thereto at room temperature, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure. The residue was purified by column chromatography using a hexane-acetone system to give 2-(3,4-dimethoxy-benzoylamino)-thiophene-3-carboxylic acid methyl ester (320 mg, yield 100%).

Separately, phosphorus oxychloride (100 μl) was added dropwise to N,N-dimethylformamide (29 mg) at 0° C., and the mixture was stirred at that temperature for 5 min. Subsequently, the reaction system was heated to 80° C., 2-(3,4-dimethoxy-benzoylamino)-thiophene-3-carboxylic acid methyl ester (64 mg: dissolved in 1 ml of N,N-dimethylformamide) produced by the above reaction was then added dropwise thereto, and the mixture was stirred at that temperature for 2 hr. After the completion of the reaction, the reaction solution was neutralized with a saturated sodium hydrogencarbonate solution, and was then subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure to give crude 2-(3,4-dimethoxy-benzoylamino)-5-formylthiophene-3-carboxylic acid methyl ester (70 mg, crude yield 100%).

Crude 2-(3,4-dimethoxy-benzoylamino)-5-formylthiophene-3-carboxylic acid methyl ester (35 mg) synthesized by the above process was dissolved in tetrahydrofuran/N,N-dimethylformamide=1/1 (10 ml). Sodium borohydride (22 mg) was added to the solution at room temperature, and the mixture was stirred at that temperature for 20 min. After the completion of the reaction, distilled water was added thereto at room temperature, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure to give crude 2-(3,4-dimethoxy-benzoylamino)-5-hydroxymethyl-thiophene-3-carboxylic acid methyl ester (35 mg, crude yield 100%).

Subsequently, crude 2-(3,4-dimethoxy-benzoylamino)-5-hydroxy-methyl-thiophene-3-carboxylic acid methyl ester (crude 35 mg) synthesized by the above process was dissolved in anhydrous methylene chloride (5 ml). Pyridine (24 mg: dissolved in 1 ml of anhydrous methylene chloride) and acetic anhydride (31 mg: dissolved in 1 ml of anhydrous methylene chloride) were added dropwise to the solution at room temperature, and the mixture was stirred at that temperature for 12 hr. After the completion of the reaction, distilled water was added thereto at room temperature, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a chloroform-methanol system to give 5-acetoxymethyl-2-(3,4-dimethoxy-benzoylamino)-thiophene-3-carboxylic acid methyl ester as a useful intermediate (26 mg, 3 steps, yield 67%).

5-Acetoxymethyl-2-(3,4-dimethoxy-benzoylamino)-thiophene-3-carboxylic acid methyl ester (26 mg) produced by the above process was dissolved in ethanol/tetrahydrofuran=5/2 (7 ml), and 10% palladium-carbon (10 mg) was added to the solution at room temperature. The air in the reaction system was replaced by hydrogen, and the mixture was then stirred at that temperature for 12 hr. After the completion of the reaction, the atmosphere in the reaction system was replaced by nitrogen, and the reaction solution was then filtered through Celite to remove 10% palladium-carbon and was then concentrated under the reduced pressure. The residue was purified by column chromatography using a hexane-acetone system to give 2-(3,4-dimethoxy-benzoylamino)-5-methyl-thiophene-3-carboxylic acid methyl ester (13 mg, yield 59%).

Subsequently, 2-(3,4-dimethoxy-benzoylamino)-5-methyl-thiophene-3-carboxylic acid methyl ester (16 mg) synthesized by the above process was dissolved in ethanol (5 ml). Hydrazine (1 ml) was then added to the solution at room temperature, and the mixture was stirred at that temperature for 12 hr. After the completion of the reaction, the reaction system was concentrated under the reduced pressure, and the residue was purified by column chromatography eluted with a chloroform-methanol system to give N-(3-hydrazinocarbonyl)-5-methylthiophen-2-yl)-3,4-dimethoxy-benzamide (8.0 mg, yield 50%).

Subsequently, N-(3-hydrazinocarbonyl)-5-methylthiophen-2-yl)-3,4-dimethoxy-benzamide (8.0 mg) was dissolved in anhydrous toluene (5 ml), 4-chloro-3-(trifluoromethyl)benzaldehyde (compound C) (15 mg: dissolved in 1 ml of anhydrous toluene) and a catalytic amount of acetic acid were added dropwise to the solution at room temperature, and the mixture was stirred at that temperature for 3 hr. After the completion of the reaction, the reaction solution was neutralized with a saturated sodium hydrogencarbonate solution and was then subjected to separatory extraction with ethyl acetate. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a chloroform-methanol system to give the title compound 955 (5.0 mg, yield 38%).

¹H-NMR (CDCL₃, 400 MHz): δ 12.66 (1H, bs), 9.19 (1H, bs), 8.19 (1H, bs), 8.02 (1H, s), 7.80-7.92 (1H, m), 7.62-7.65 (2H, m), 7.56 (1H, d, J=8.3 Hz), 6.92 (1H, d, J=8.8 Hz), 3.97 (3H, s), 3.95 (3H, s), 2.44 (3H, s)

Mass spectrometric value (ESI-MS) 524 (M−1)

Example O

Compound 956 N-[3-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-methyl-5-piperidin-1-ylmethyl-thiophen-2-yl]-3-diethylaminomethyl-benzamide

Ethyl-2-amino-4-methylthiophene-3-carboxylate (compound A) (370 mg) was dissolved in anhydrous methylene chloride (10 ml). Pyridine (240 mg: dissolved in 2 ml of anhydrous methylene chloride) and 3-(chloromethyl)benzoyl chloride (compound B) (570 mg: dissolved in 2 ml of anhydrous methylene chloride) were added dropwise to the solution at 0° C., and the mixture was stirred at room temperature for 12 hr. After the completion of the reaction, distilled water was added thereto at room temperature, and the mixture was then subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a chloroform-methanol system to give 2-(3-chloromethylbenzoylamino)-4-methyl-thiophene-3-carboxylic acid ethyl ester (670 mg, yield 99%).

Subsequently, 2-(3-diethylaminomethyl-benzoylamino)-4-methyl-thiophene-3-carboxylic acid ethyl ester (700 mg) synthesized by the above process was dissolved in anhydrous methylene chloride (10 ml). Triethylamine (425 mg: dissolved in 2 ml of anhydrous methylene chloride) and diethylamine (compound B′) (310 mg: dissolved in 2 ml of anhydrous methylene chloride) were added dropwise to the solution at 0° C., and the mixture was stirred at room temperature for 2 hr. After the completion of the reaction, distilled water was added thereto at room temperature, and the mixture was then subjected to separatory extraction with chloroform, and the organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a chloroform-methanol system to give 2-(3-diethylaminomethyl-benzoylamino)-4-methylthiophene-3-carboxylic acid ethyl ester (690 mg, yield 88%).

Separately, phosphorus oxychloride (200 μl) was added dropwise to N,N-dimethylformamide (73 mg) at 0° C., and the mixture was stirred at that temperature for 5 min. The reaction system was heated to 80° C., 2-(3-diethylaminomethyl-benzoylamino)-4-methyl-thiophene-3-carboxylic acid ethyl ester (187 mg) synthesized by the above process was then added thereto, and the mixture was stirred at that temperature for 3 hr. After the completion of the reaction, the reaction solution was neutralized with a saturated sodium hydrogencarbonate solution, and was then subjected to separatory extraction with chloroform, and the organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a chloroform-methanol system to give 2-(3-diethylaminomethyl-benzoylamino)-5-formyl-4-methylthiophene-3-carboxylic acid ethyl ester as a useful intermediate (110 mg, yield 53%).

2-(3-diethylaminomethyl-benzoylamino)-5-formyl-4-methyl-thiophene-3-carboxylic acid ethyl ester (110 mg) synthesized by the above process was dissolved in N,N-dimethylformamide (10 ml), acetic acid (100 μl) and sodium triacetoxyborohydride (66 mg) were added to the solution at room temperature, and the mixture was stirred at that temperature for one hr. After the completion of the reaction, the reaction solution was neutralized with a saturated sodium hydrogencarbonate solution, and was then subjected to separatory extraction with ethyl acetate. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a chloroform-methanol system to give 2-(3-diethylaminomethyl-benzoylamino)-4-methyl-5-piperidin-1-ylmethylthiophene-3-carboxylic acid ethyl ester (79 mg, yield 64%).

Subsequently, 2-(3-diethylaminomethyl-benzoylamino)-4-methyl-5-piperidin-1-ylmethylthiophene-3-carboxylic acid ethyl ester (79 mg) was dissolved in ethanol (10 ml), hydrazine monohydrate (2 ml) was added dropwise to the solution at room temperature, and a reaction was then allowed to proceed at that temperature for 12 hr. After the completion of the reaction, the reaction system was concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a chloroform-methanol system to give 3-diethylaminomethyl-N-(3-hydrazinocarbonyl-4-methyl-5-piperidin-1-ylmethylthiophen-2-yl)-benzamide as a useful intermediate (30 mg, yield 38%).

Subsequently, 3-diethylaminomethyl-N-(3-hydrazinocarbonyl-4-methyl-5-piperidin-1-ylmethylthiophen-2-yl)-benzamide (15 mg) produced by the above process was dissolved in anhydrous toluene. 4-Chloro-3-(trifluoromethyl)benzaldehyde (compound C) (21 mg: dissolved in 1 ml of anhydrous toluene) and a catalytic amount of acetic acid were added dropwise to the solution at room temperature, and the mixture was then stirred at that temperature for 3 hr. After the completion of the reaction, the reaction solution was neutralized with a saturated sodium hydrogencarbonate solution, and was then subjected to separatory extraction with ethyl acetate, and the organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a chloroform-methanol system to give the title compound 956 (6.0 mg, yield 29%).

¹H-NMR (CDCL₃, 400 MHz): δ 8.26 (1H, bs), 8.05 (1H, s), 8.00 (1H, s), 7.95 (1H, d, J=8.0 Hz), 7.88 (1H, d, J=7.6 Hz), 7.55-7.62 (2H, m), 7.42-7.48 (1H, m), 3.67 (2H, s), 2.48-2.60 (10H, m), 1.24-2.00 (9H, m), 1.07 (6H, t, J=7.1 Hz)

Mass spectrometric value (ESI-MS) 646 (M−1)

Compound 957 3-Diethylaminomethyl-N-[3-(4-methoxy-benzylidene-hydrazinocarbonyl)-4-methyl-5-piperidin-1-ylmethyl-thiophen-2-yl]-benzamide

The title compound 957 was produced in substantially the same manner as in Example O.

¹H-NMR (CDCL₃, 400 MHz): δ 8.08 (1H, bs), 7.99 (1H, bs), 7.90 (1H, d, J=7.8 Hz), 7.74 (2H, d, J=8.3 Hz), 7.60 (1H, d, J=7.6 Hz), 7.40-7.45 (1H, m), 6.94 (2H, d, J=8.8 Hz), 3.86 (3H, s), 3.67 (2H, s), 2.40-2.60 (10H, m), 1.25-1.62 (9H, m), 1.06 (6H, t, J=7.1 Hz)

Mass spectrometric value (ESI-MS) 574 (M−1) 598 (M+23)

Compound 958 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[2-(4-methoxy-benzylidene-hydrazinocarbonyl)-4-piperidin-1-yl-phenyl]-benzamide

The title compound 958 was produced in substantially the same manner as in Example J.

¹H-NMR (CD₃OD, 400 MHz): δ 8.38 (1H, dd, J=6.1 Hz, J=9.0 Hz), 8.29 (1H, s), 8.01 (1H, bs), 7.86 (1H, d, J=7.4 Hz), 7.75-7.85 (2H, m), 7.59 (1H, d, J=7.3 Hz), 7.48 (1H, dd, J=7.6 Hz, J=7.8 Hz), 7.37 (1H, d, J=2.7 Hz), 7.22 (1H, dd, J=3.0 Hz, J=9.0 Hz), 6.90-7.03 (2H, m), 3.80-3.90 (7H, m), 3.22-3.30 (4H, m), 2.40-2.60 (4H, m), 1.70-1.89 (4H, m), 1.62-1.64 (2H, m), 1.08 (3H, d, J=6.3 Hz), 1.07 (3H, d, J=6.1 Hz)

Mass spectrometric value (ESI-MS) 600, 601 (M−1) 622 (M−1+23)

Example P

Compound 959 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[3-(3-fluoro-benzylidene-hydrazinocarbonyl)-naphthalen-2-yl]-benzamide

3-Amino-naphthalene-2-carboxylic acid (compound A′) (1.2 g) was dissolved in anhydrous methylene chloride (12 ml). 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.5 g), 1-hydroxybenzotriazole monohydrate (1.5 g), and triethylamine (1 ml) were added to the solution at room temperature, and the mixture was then stirred at that temperature for 12 hr. After the completion of the reaction, distilled water was added thereto at room temperature, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure. The residue was purified by column chromatography using a hexane-acetone system to give 3-amino-naphthalene-2-carboxylic acid methyl ester as a useful intermediate (compound A) (530 mg, yield 41%).

3-Amino-naphthalene-2-carboxylic acid methyl ester (compound A) (530 mg) produced by the above process was dissolved in anhydrous methylene chloride (10 ml). Pyridine (0.5 ml) and 3-(chloromethyl)benzoyl chloride (compound B) (0.6 ml) was added dropwise to the solution at room temperature, and the mixture was then stirred at that temperature for 30 min. After the completion of the reaction, distilled water was added thereto at room temperature, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was concentrated under the reduced pressure to precipitate crystals. The crystals were collected by Kiriyama Rohto and were washed with a hexane-ether solvent to give 3-(3-chloromethylbenzoylamino)-naphthalene-2-carboxylic acid methyl ester (870 mg, yield 93%).

Subsequently, 3-(3-chloromethyl-benzoylamino)-naphthalene-2-carboxylic acid methyl ester (870 mg) was dissolved in anhydrous methylene chloride (15 ml). Pyridine (400 μl) and diisopropanolamine (compound B′) (1.0 g) were added to the solution at room temperature, and the mixture was then stirred at that temperature for 48 hr. After the completion of the reaction, distilled water was added thereto at room temperature, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a hexane-acetone system to give 3-(3-{[bis-(2-hydroxy-propyl)-amino]-methyl}-benzoylamino)-naphthalene-2-carboxylic acid methyl ester as a useful intermediate (640 mg).

3-(3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-benzoylamino)-naphthalene-2-carboxylic acid methyl ester (640 mg) produced by the above reaction was dissolved in ethanol (7 ml). Hydrazine monohydrate (1 ml) was added dropwise to the solution at room temperature, and the mixture was then stirred at that temperature for 2 hr. After the completion of the reaction, the reaction solution was concentrated under the reduced pressure, and the residue was purified by column chromatography eluted with a chloroform-methanol system to give 3-{[bis-(2-hydroxy-propyl)amino]-methyl}-N-(3-hydrazinocarbonylnaphthalen-2-yl)-benzamide (350 mg, yield 54%).

Subsequently, 3-{[bis-(2-hydroxy-propyl)amino]-methyl}-N-(3-hydrazinocarbonylnaphthalen-2-yl)-benzamide (50 mg) was dissolved in anhydrous toluene (1 ml). 3-Fluorobenzaldehyde (compound C) (50 μl) was added dropwise to the solution at room temperature, and the mixture was then stirred at 120° C. for 12 hr. After the completion of the reaction, the reaction solution was allowed to stand for cooling at room temperature and the reaction system was then concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a hexane-acetone system to give the title compound 959 (32 mg, yield 51%).

¹H-NMR (CDCL₃, 400 MHz): δ 12.05 (1H, bs), 11.40-11.55 (1H, m), 8.86 (1H, d, J=18.6 Hz), 8.10-8.40 (3H, m), 7.88 (1H, dd, J=7.3 Hz, J=17.8 Hz), 7.66 (2H, d, J=8.3 Hz), 7.25-7.50 (5H, m), 7.05-7.15 (2H, m), 6.80-6.95 (1H, m), 4.15-4.25 (2H, m), 3.95-4.05 (2H, m), 3.89 (1H, s), 3.60 (1H, d, J=1.4 Hz), 2.48-2.83 (4H, m), 1.20 (3H, d, J=6.1 Hz), 1.14 (3H, d, J=6.3 Hz)

Mass spectrometric value (ESI-MS) 555 (M−1)

Compound 960 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[3-(4-methyl-benzylidene-hydrazinocarbonyl)-naphthalen-2-yl]-benzamide

The title compound 960 was produced in substantially the same manner as in Example P.

¹H-NMR (CDCL₃, 400 MHz): δ 11.90 (1H, bs), 10.90-11.00 (1H, m), 8.85 (1H, bs), 8.30 (1H, d, J=3.9 Hz), 7.86-8.20 (3H, m), 7.52-7.64 (3H, m), 7.28-7.46 (4H, m), 7.06-7.18 (1H, m), 6.88 (2H, d, J=7.8 Hz), 3.80-3.96 (4H, m), 3.55-3.60 (1H, m), 2.40-2.70 (4H, m), 2.18-2.23 (3H, m), 1.10 (3H, d, J=6.1 Hz), 1.06 (3H, d, J=6.1 Hz)

Mass spectrometric value (ESI-MS) 551 (M−1)

Compound 961 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[3-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-naphthalen-2-yl]-benzamide

The title compound 961 was produced in substantially the same manner as in Example P.

¹H-NMR (CDCL₃, 400 MHz): δ 11.95-12.05 (1H, m), 10.80-10.95 (1H, m), 8.95-9.02 (1H, m), 8.15-8.32 (3H, m), 7.95-8.05 (1H, m), 7.20-7.80 (8H, m), 6.87 (1H, d, J=7.3 Hz), 3.60-4.20 (4H, m), 2.28-2.75 (4H, m), 2.00-2.15 (6H, m), 1.10-1.17 (6H, m)

Mass spectrometric value (ESI-MS) 565 (M−1)

Compound 962 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[3-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-naphthalen-2-yl]-benzamide

The title compound 962 was produced in substantially the same manner as in Example P.

¹H-NMR (CDCL₃, 400 MHz): δ 11.96-12.05 (1H, m), 11.71 (1H, d, J=15.1 Hz), 8.80 (1H, s), 8.32 (2H, bs), 8.13 (1H, d, J=7.8 Hz), 7.57-7.94 (4H, m), 7.25-7.46 (5H, m), 7.08 (2H, d, J=8.0 Hz), 3.50-4.20 (5H, m), 2.30-2.86 (4H, m), 1.13 (3H, d, J=6.1 Hz), 1.09 (3H, d, J=6.3 Hz)

Mass spectrometric value (ESI-MS) 639, 641, 642 (M−1)

Compound 963 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[3-(4-methoxy-benzylidene-hydrazinocarbonyl)-naphthalen-2-yl]-benzamide

The title compound 963 was produced in substantially the same manner as in Example P.

¹H-NMR (CDCL₃, 400 MHz): δ 11.95 (1H, bs), 10.86-11.00 (1H, m), 8.80-8.90 (1H, m), 8.05-8.30 (3H, m), 7.85-7.95 (1H, m), 7.60-7.65 (3H, m), 7.22-7.48 (4H, m), 7.06-7.18 (1H, m), 6.59 (1H, d, J=8.5 Hz), 3.50-3.96 (8H, m), 2.40-2.70 (4H, m), 1.10 (3H, d, J=6.1 Hz), 1.06 (3H, d, J=6.1 Hz)

Mass spectrometric value (ESI-MS) 567 (M−1) 591 (M+23)

Compound 964 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[3-(3-fluoro-benzylidene-hydrazinocarbonyl)-pyridin-2-yl]-benzamide

The title compound 964 was produced in substantially the same manner as in Example P.

¹H-NMR (CD₃OD, 400 MHz): δ 8.55-8.60 (1H, m), 8.29 (1H, s), 8.25 (1H, d, J=7.8 Hz), 8.07 (1H, s), 7.89-7.96 (1H, m), 7.70 (1H, d, J=10.0 Hz), 7.62 (1H, d, J=7.6 Hz), 7.57 (1H, d, J=7.3 Hz), 7.40-7.52 (2H, m), 7.32-7.40 (1H, m), 7.13-7.20 (1H, m), 3.60-3.95 (4H, m), 2.35-2.60 (4H, m), 1.08 (3H, d, J=6.1 Hz), 1.07 (3H, d, J=6.3 Hz)

Mass spectrometric value (ESI-MS) 506, 507, 508 (M−1)

Compound 965 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[3-(4-methyl-benzylidene-hydrazinocarbonyl)-pyridin-2-yl]-benzamide

The title compound 965 was produced in substantially the same manner as in Example P.

¹H-NMR (CD₃OD, 400 MHz): δ 8.54-8.59 (1H, m), 8.21-8.28 (2H, m), 8.05-8.09 (1H, m), 7.86-7.95 (1H, m), 7.72 (2H, d, J=7.8 Hz), 7.62 (1H, d, J=7.8 Hz), 7.49 (1H, ddd, J=1.7 Hz, J=7.6 Hz, J=7.6 Hz), 7.32-7.37 (1H, m), 7.25 (2H, d, J=7.8 Hz), 3.81-3.93 (4H, m), 2.39-2.60 (4H, m), 2.37 (3H, s), 1.08 (3H, d, J=6.1 Hz), 1.07 (3H, d, J=6.4 Hz)

Mass spectrometric value (ESI-MS) 502, 503, 504 (M−1) 526, 527 (M+23)

Compound 966 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[3-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-pyridin-2-yl]-benzamide

The title compound 966 was produced in substantially the same manner as in Example P.

¹H-NMR (CD₃OD, 400 MHz): δ 8.50-8.60 (1H, m), 8.23-8.28 (2H, m), 8.05-8.08 (1H, m), 7.88-7.98 (1H, m), 7.60-7.66 (2H, m), 7.46-7.56 (2H, m), 7.25-7.40 (1H, m), 7.18-7.22 (1H, m), 3.75-3.94 (4H, m), 2.38-2.60 (4H, m), 2.31 (3H, s), 2.30 (3H, s), 1.08 (3H, d, J=6.1 Hz), 1.07 (3H, d, J=6.1 Hz)

Mass spectrometric value (ESI-MS) 516, 517 (M−1) 540, 541 (M+23)

Compound 967 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[3-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-pyridin-2-yl]-benzamide

The title compound 967 was produced in substantially the same manner as in Example P.

¹H-NMR (CDCL₃, 400 MHz): δ 11.70-11.85 (1H, m), 11.61 (1H, s), 8.58 (1H, s), 8.36 (1H, s), 8.24 (1H, s), 8.00-8.10 (2H, m), 7.80-7.90 (1H, m), 7.40-7.55 (4H, m), 6.75-6.85 (1H, m), 3.86-4.10 (4H, m), 2.45-2.75 (4H, m), 1.10 (6H, d, J=6.1 Hz)

Mass spectrometric value (ESI-MS) 592 (M−1) 614 (M+23)

Compound 968 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[3-(4-methoxy-benzylidene-hydrazinocarbonyl)-pyridin-2-yl]-benzamide

The title compound 968 was produced in substantially the same manner as in Example P.

¹H-NMR (CDCL₃, 400 MHz): δ 11.74 (1H, s), 11.00-11.20 (1H, m), 8.40-8.45 (1H, m), 8.22 (1H, d, J=12.4 Hz), 8.06 (1H, s), 7.80-7.90 (3H, m), 7.35-7.50 (3H, m), 6.80-7.00 (3H, m), 3.80-3.90 (7H, m), 2.40-2.75 (4H, m), 1.05-1.14 (6H, m)

Mass spectrometric value (ESI-MS) 518 (M−1) 542 (M+23)

Compound 969 N-[3-(3-Fluoro-benzylidene-hydrazinocarbonyl)-naphthalen-2-yl]-3-[4-(2-hydroxy-ethyl)-piperazin-1-ylmethyl]-benzamide

The title compound 969 was produced in substantially the same manner as in Example P.

¹H-NMR (CDCL₃, 400 MHz): δ 11.15 (1H, s), 10.91 (1H, bs), 7.10-8.90 (15H, m), 3.60-3.75 (4H, m), 2.00-2.85 (11H, m)

Mass spectrometric value (ESI-MS) 552, 553 (M−1)

Compound 970 3-[4-(2-Hydroxy-ethyl)-piperazin-1-ylmethyl]-N-[3-(4-methyl-benzylidene-hydrazinocarbonyl)-naphthalen-2-yl]-benzamide

The title compound 970 was produced in substantially the same manner as in Example P.

¹H-NMR (CDCL₃, 400 MHz): δ 11.19 (1H, s), 7.00-8.95 (15H, m), 3.63 (2H, s), 3.59 (2H, t, J=5.4 Hz), 2.50-2.65 (10H, m), 2.40 (3H, s)

Mass spectrometric value (ESI-MS) 548, 549, 550 (M−1)

Compound 971 N-[3-(3,4-Dimethyl-benzylidene-hydrazinocarbonyl)-naphthalen-2-yl]-3-[4-(2-hydroxy-ethyl)-piperazin-1-ylmethyl]-benzamide

The title compound 971 was produced in substantially the same manner as in Example P.

¹H-NMR (CDCL₃, 400 MHz): δ 11.19 (1H, s), 7.00-9.00 (14H, m), 3.63 (2H, s), 3.59 (2H, t, J=5.4 Hz), 2.50-2.75 (10H, m), 2.32 (3H, s), 2.30 (3H, s)

Mass spectrometric value (ESI-MS) 562, 563 (M−1)

Compound 972 N-[3-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-naphthalen-2-yl]-3-[4-(2-hydroxy-ethyl)-piperazin-1-ylmethyl]-benzamide

The title compound 972 was produced in substantially the same manner as in Example P.

¹H-NMR (CDCL₃, 400 MHz): δ 11.19 (1H, s), 8.97 (1H, s), 7.20-8.60 (13H, m), 3.64 (2H, s), 3.57-3.63 (2H, m), 2.50-2.60 (10H, m)

Mass spectrometric value (ESI-MS) 636, 637 (M−1)

Compound 973 3-[4-(2-Hydroxy-ethyl)-piperazin-1-ylmethyl]-N-[3-(4-methoxy-benzylidene-hydrazinocarbonyl)-naphthalen-2-yl]-benzamide

The title compound 973 was produced in substantially the same manner as in Example P.

¹H-NMR (CDCL₃, 400 MHz): δ 11.25 (1H, s), 10.47 (1H, s), 8.88 (1H, s), 8.48 (1H, s), 7.97 (2H, bs), 7.82 (2H, d, J=8.3 Hz), 7.74 (1H, d, J=7.3 Hz), 7.63 (1H, d, J=8.5 Hz), 7.53 (1H, d, J=7.6 Hz), 7.38-7.43 (3H, m), 7.10-7.20 (1H, m), 6.96 (2H, d, J=8.3 Hz), 3.86 (3H, s), 3.62 (2H, s), 3.59 (2H, t, J=5.4 Hz), 2.50-2.60 (10H, m)

Mass spectrometric value (ESI-MS) 564, 565 (M−1)

Compound 974 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[4-(3-fluoro-benzylidene-hydrazinocarbonyl)-thiophen-3-yl]-benzamide

The title compound 974 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCL₃, 400 MHz): δ 8.91 (1H, s), 7.95-8.27 (5H, m), 7.00-7.70 (6H, m), 3.82-4.08 (4H, m), 2.40-2.75 (4H, m), 1.10-1.17 (6H, m)

Mass spectrometric value (ESI-MS) 511, 512 (M−1) 534 (M+23)

Compound 975 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[4-(3-methyl-benzylidene-hydrazinocarbonyl)-thiophen-3-yl]-benzamide

The title compound 975 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCL₃, 400 MHz): δ 11.99 (1H, s), 11.28-11.38 (1H, m), 8.36 (1H, s), 7.95-8.20 (4H, m), 7.68-7.73 (1H, m), 7.35-7.45 (1H, m), 7.15-7.34 (2H, m), 6.87-6.97 (2H, m), 4.10-4.20 (1H, m), 3.85-4.00 (3H, m), 3.65-3.75 (1H, m), 2.62-2.85 (1H, m), 2.30-2.58 (4H, m), 2.15 (3H, s), 1.14 (3H, d, J=6.1 Hz), 1.08 (3H, d, J=6.3 Hz)

Mass spectrometric value (ESI-MS) 507, 508 (M−1) 531 (M+23)

Compound 976 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[4-(4-methyl-benzylidene-hydrazinocarbonyl)-thiophen-3-yl]-benzamide

The title compound 976 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCL₃, 400 MHz): δ 8.99 (1H, s), 7.95-8.30 (4H, m), 7.30-7.70 (4H, m), 7.26 (1H, d, J=6.1 Hz), 7.13 (2H, d, J=7.1 Hz), 3.38-4.05 (4H, m), 2.34-2.70 (7H, m), 1.08-1.15 (6H, m)

Mass spectrometric value (ESI-MS) 507, 508 (M−1) 531 (M+23)

Compound 977 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[4-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-thiophen-3-yl]-benzamide

The title compound 977 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCL₃, 400 MHz): δ 11.98 (1H, s), 11.12-11.25 (1H, m), 8.30-8.40 (1H, m), 7.96-8.18 (4H, m), 7.70-7.80 (1H, m), 7.20-7.50 (3H, m), 6.75-6.85 (1H, m), 3.65-4.20 (4H, m), 2.45-2.55 (2H, m), 2.20-2.30 (3H, m), 2.10-2.14 (3H, m), 2.02-2.08 (3H, m), 1.14 (3H, d, J=6.1 Hz), 1.08 (3H, d, J=6.3 Hz)

Mass spectrometric value (ESI-MS) 521, 522 (M−1) 545 (M+23)

Compound 978 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[4-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-thiophen-3-yl]-benzamide

The title compound 978 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCL₃, 400 MHz): δ 11.85 (1H, d, J=5.1 Hz), 11.65-11.80 (1H, m), 8.28-8.35 (1H, m), 7.98-8.20 (3H, m), 7.65-7.85 (2H, m), 7.02-7.52 (4H, m), 3.60-4.20 (4H, m), 2.46-2.90 (4H, m), 1.14 (3H, d, J=6.1 Hz), 1.09 (3H, d, J=6.1 Hz)

Mass spectrometric value (ESI-MS) 595, 597 (M−1) 619, 621 (M+23)

Compound 979 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[4-(4-methoxy-benzylidene-hydrazinocarbonyl)-thiophen-3-yl]-benzamide

The title compound 979 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCL₃, 400 MHz): δ 12.03 (1H, d, J=10.5 Hz), 11.16-11.30 (1H, m), 8.30-8.40 (1H, m), 7.95-8.15 (3H, m), 7.75 (1H, dd, J=3.2 Hz, J=7.6 Hz), 7.36-7.44 (3H, m), 7.28-7.32 (1H, m), 6.45-6.57 (2H, m), 3.65-4.20 (7H, m), 2.44-2.84 (4H, m), 1.13 (3H, d, J=6.1 Hz), 1.07 (3H, d, J=6.4 Hz)

Mass spectrometric value (ESI-MS) 523, 524 (M−1) 547 (M+23)

Compound 980 N-[4-(3-Fluoro-benzylidene-hydrazinocarbonyl)-thiophen-3-yl]-3-[4-(2-hydroxy-ethyl)-piperazin-1-ylmethyl]-benzamide

The title compound 980 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCL₃, 400 MHz): δ 8.26 (1H, s), 7.97 (1H, s), 7.87 (1H, d, J=7.8 Hz), 7.00-7.54 (8H, m), 3.59-3.66 (4H, m), 2.50-2.75 (10H, m)

Mass spectrometric value (ESI-MS) 508, 509 (M−1) 532 (M+23)

Compound 981 3-[4-(2-Hydroxy-ethyl)-piperazin-1-ylmethyl]-N-[4-(4-methyl-benzylidene-hydrazinocarbonyl)-thiophen-3-yl]-benzamide

The title compound 981 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCL₃, 400 MHz): δ 11.81 (1H, bs), 11.50 (1H, bs), 8.24 (1H, s), 7.95 (1H, s), 7.87 (2H, d, J=7.6 Hz), 7.37-7.70 (5H, m), 7.18-7.25 (2H, m), 3.58 (4H, s), 2.37 (3H, s), 2.40-2.55 (10H, m)

Mass spectrometric value (ESI-MS) 504, 505 (M−1) 528 (M+23)

Compound 982 N-[4-(3,4-Dimethyl-benzylidene-hydrazinocarbonyl)-thiophen-3-yl]-3-[4-(2-hydroxy-ethyl)-piperazin-1-ylmethyl]-benzamide

The title compound 982 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCL₃, 400 MHz): δ 8.22-8.28 (1H, m), 7.95 (1H, s), 7.87 (1H, d, J=7.6 Hz), 7.30-7.56 (6H, m), 7.10-7.20 (1H, m), 3.57 (4H, s), 2.40-2.60 (10H, m), 2.28 (6H, s)

Mass spectrometric value (ESI-MS) 518, 519 (M−1) 542 (M+23)

Compound 983 N-[4-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-thiophen-3-yl]-3-[4-(2-hydroxy-ethyl)-piperazin-1-ylmethyl]-benzamide

The title compound 983 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCL₃, 400 MHz): δ 11.39 (1H, bs), 8.22 (1H, s), 7.82-8.00 (5H, m), 7.40-7.60 (4H, m), 3.55-3.62 (4H, m), 2.45-2.60 (10H, m)

Mass spectrometric value (ESI-MS) 592, 594 (M−1) 616 (M+23)

Compound 984 3-[4-(2-Hydroxy-ethyl)-piperazin-1-ylmethyl]-N-[4-(4-methoxy-benzylidene-hydrazinocarbonyl)-thiophen-3-yl]-benzamide

The title compound 984 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCL₃, 400 MHz): δ 11.86 (1H, bs), 11.51 (1H, bs), 8.25 (1H, d, J=3.4 Hz), 7.95 (1H, s), 7.87 (2H, d, J=7.3 Hz), 7.55-7.75 (2H, m), 7.49 (1H, d, J=7.3 Hz), 7.41 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.20-7.28 (1H, m), 6.85-7.30 (2H, m), 3.83 (3H, s), 3.58 (4H, s), 2.45-2.60 (10H, m)

Mass spectrometric value (ESI-MS) 520, 521 (M−1)

Compound 985 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-4-fluoro-phenyl]-benzamide

The title compound 985 was produced in substantially the same manner as in Example P.

¹H-NMR (CDCL₃, 400 MHz): δ 12.30-12.40 (1H, m), 8.55-8.65 (1H, m), 8.24-8.32 (1H, m), 8.14 (1H, s), 7.92-8.00 (1H, m), 7.56 (1H, s), 7.39 (1H, dd, J=7.3 Hz, J=7.3 Hz), 7.31 (1H, s), 7.16-7.28 (2H, m), 6.92-7.02 (1H, m), 6.76-6.86 (1H, m), 3.80-4.15 (4H, m), 3.55-3.65 (1H, m), 2.40-2.75 (4H, m), 2.14 (3H, s), 2.06 (3H, s), 1.10 (3H, d, J=6.4 Hz), 1.06 (3H, d, J=6.1 Hz)

Mass spectrometric value (ESI-MS) 533, 534 (M−1)

Compound 986 2-(3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-benzoylamino)-N-[2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-4-fluoro-phenyl]-5-fluoro-benzamide

The title compound 986 was produced in substantially the same manner as in Example P.

¹H-NMR (CDCL₃, 400 MHz): δ 11.95-12.05 (1H, m), 11.16 (1H, bs), 10.93 (1H, bs), 8.75-8.85 (1H, m), 8.20-8.40 (1H, m), 7.20-8.10 (11H, m), 6.92-7.05 (1H, m), 3.70-3.95 (4H, m), 2.35-2.60 (4H, m), 2.12-2.21 (6H, m), 0.96-1.02 (6H, m)

Mass spectrometric value (ESI-MS) 670 (M−1)

Compound 987 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[4-fluoro-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 987 was produced in substantially the same manner as in Example P.

¹H-NMR (CD₃OD, 400 MHz): δ 8.60-8.66 (1H, m), 8.35 (1H, s), 8.09 (1H, d, J=5.9 Hz), 7.95 (1H, d, J=8.0 Hz), 7.38-7.83 (7H, m), 7.15-7.28 (1H, m), 3.80-4.10 (4H, m), 2.58-2.75 (4H, m), 1.12 (3H, d, J=6.1 Hz), 1.11 (3H, d, J=6.4 Hz)

Mass spectrometric value (ESI-MS) 523, 524 (M−1) 547 (M+23)

Compound 988 2-(3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-benzoylamino)-5-fluoro-N-[4-fluoro-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 988 was produced in substantially the same manner as in Example P.

¹H-NMR (CD₃OD, 400 MHz): δ 8.52-8.67 (1H, m), 8.32-8.40 (1H, m), 8.27 (1H, s), 7.36-8.08 (11H, m), 7.13-7.20 (1H, m), 3.60-3.95 (4H, m), 2.38-2.57 (4H, m), 1.02-1.10 (6H, m)

Mass spectrometric value (ESI-MS) 660, 661 (M−1) 684 (M+23)

Compound 989 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[4-fluoro-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 989 was produced in substantially the same manner as in Example P.

¹H-NMR (CD₃OD, 400 MHz): δ 8.60-8.67 (1H, m), 8.31 (1H, s), 8.02-8.07 (1H, m), 7.87-7.92 (1H, m), 7.75 (2H, d, J=7.8 Hz), 7.67 (1H, dd, J=2.7 Hz, J=9.0 Hz), 7.61 (1H, d, J=7.3 Hz), 7.50 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.36-7.43 (1H, m), 7.26 (2H, d, J=7.8 Hz), 3.65-3.95 (4H, m), 2.40-2.60 (4H, m), 2.38 (3H, s), 1.09 (3H, d, J=6.1 Hz), 1.08 (3H, d, J=6.1 Hz)

Mass spectrometric value (ESI-MS) 519, 520 (M−1) 543 (M+23)

Compound 990 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[4-fluoro-2-(4-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 990 was produced in substantially the same manner as in Example P.

¹H-NMR (CD₃OD, 400 MHz): δ 8.61-8.67 (1H, m), 8.29 (1H, s), 8.03-8.07 (1H, m), 7.87-7.92 (1H, m), 7.81 (2H, d, J=8.5 Hz), 7.66 (1H, dd, J=2.7 Hz, J=9.3 Hz), 7.61 (1H, d, J=7.1 Hz), 7.50 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.38-7.42 (1H, m), 6.99 (2H, d, J=8.8 Hz), 3.82-3.93 (4H, m), 3.84 (3H, s), 2.40-2.60 (4H, m), 1.09 (3H, d, J=6.4 Hz), 1.08 (3H, d, J=6.1 Hz)

Mass spectrometric value (ESI-MS) 535, 536, 537 (M−1) 559 (M+23)

Compound 991 N-[5-Tert-butyl-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-thiophen-3-yl]-3-[4-(2-hydroxy-ethyl)-piperazin-1-ylmethyl]-benzamide

The title compound 991 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 8.15 (1H, s), 7.99 (1H, s), 7.88-7.97 (2H, m), 7.70 (1H, s), 7.60 (1H, d, J=7.3 Hz), 7.44-7.55 (2H, m), 7.20 (1H, d, J=7.8 Hz), 3.64-3.70 (4H, m), 2.53-2.70 (10H, m), 2.32 (3H, s), 2.31 (3H, s), 1.50 (9H, s)

Mass spectrometric value (ESI-MS) 574, 575, 576 (M−1)

Compound 992 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[2-(3-fluoro-benzylidene-hydrazinocarbonyl)-thiophen-3-yl]-benzamide

The title compound 992 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 8.26-8.34 (1H, m), 7.15-8.13 (10H, m), 3.80-4.08 (4H, m), 2.55-2.70 (4H, m), 1.13 (3H, d, J=6.1 Hz), 1.12 (3H, d, J=6.1 Hz)

Mass spectrometric value (ESI-MS) 511, 512, 513 (M−1)

Compound 993 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-[2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-thiophen-3-yl]-benzamide

The title compound 993 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 8.19-8.35 (2H, m), 8.00-8.09 (3H, m), 7.83-7.94 (2H, m), 7.68 (1H, d, J=8.5 Hz), 7.58-7.65 (1H, m), 7.47-7.55 (1H, m), 3.65-3.98 (4H, m), 2.45-2.65 (4H, m), 1.03-1.14 (6H, m)

Mass spectrometric value (ESI-MS) 595, 597, 598 (M−1)

Compound 995 3-Diethylaminomethyl-N-[2-(3-fluoro-benzylidene-hydrazinocarbonyl)-thiophen-3-yl]-benzamide

The title compound 995 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCL₃, 400 MHz): δ 12.38 (1H, bs), 9.08 (1H, s), 8.39 (1H, d, J=5.6 Hz), 7.95 (1H, s), 7.84 (1H, d, J=8.1 Hz), 7.74 (1H, bs), 7.65 (1H, bs), 7.51 (1H, d, J=7.6 Hz), 7.30-7.46 (4H, m), 7.02-7.10 (1H, m), 3.59 (2H, s), 2.48 (4H, q, J=7.1 Hz), 0.99 (6H, t, J=7.1 Hz)

Mass spectrometric value (ESI-MS) 451, 452, 453 (M−1)

Compound 996 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-{4-bromo-2-[1-(3-fluoro-phenyl)-ethylidene-hydrazinocarbonyl]-phenyl}-benzamide

The title compound 996 was produced in substantially the same manner as in Example 8.

Mass spectrometric value (ESI-MS) 599 (M−1)

Compound 997 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-{4-bromo-2-[1-(4-methoxy-phenyl)-ethylidene-hydrazinocarbonyl]-phenyl}-benzamide

The title compound 997 was produced in substantially the same manner as in Example 8.

Mass spectrometric value (ESI-MS) 609, 611 (M−1)

Compound 998 3-{[Bis-(2-hydroxy-propyl)-amino]-methyl}-N-{4-chloro-2-[4-(3-dimethylamino-propoxy)-benzylidene-hydrazinocarbonyl]-phenyl}-benzamide

The title compound 998 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 8.67-8.70 (1H, m), 8.30 (1H, s), 8.06 (1H, s), 7.88-7.94 (2H, m), 7.79-7.84 (2H, m), 7.59-7.64 (2H, m), 7.47-7.54 (1H, m), 6.96-7.02 (2H, m), 4.08 (2H, t, J=6.1 Hz), 3.82-3.95 (4H, m), 2.40-2.60 (6H, m), 2.30-2.34 (6H, s), 1.95-2.05 (2H, m), 1.09 (3H, d, J=6.4 Hz), 1.08 (3H, d, J=6.1 Hz)

Mass spectrometric value (ESI-MS) 622 (M−1)

Compound 999 N-{4-Chloro-2-[4-(3-dimethylamino-propoxy)-benzylidene-hydrazinocarbonyl]-phenyl}-3-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 999 was produced in substantially the same manner as in Example 8.

¹H-NMR (CDCL₃, 400 MHz): δ 11.58 (1H, bs), 8.54 (1H, d, J=9.3 Hz), 8.26 (1H, s), 7.95 (1H, s), 7.86 (1H, d, J=7.8 Hz), 7.72 (2H, d, J=7.6 Hz), 7.50-7.56 (2H, m), 7.38-7.45 (2H, m), 6.91 (2H, d, J=8.8 Hz), 4.03 (2H, t, J=6.5 Hz), 3.60 (2H, s), 2.47-2.65 (8H, m), 2.43 (2H, t, J=7.2 Hz), 2.23 (6H, s), 2.22 (3H, s), 1.94 (2H, tt, J=6.8 Hz, J=6.8 Hz), 0.99 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 619, 620 (M−1)

Compound 1000 (4-{[5-Chloro-2-(3-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-benzoylamino)-benzoyl]-hydrazinomethyl}-phenoxy)-acetic acid

The title compound 1000 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 8.62 (1H, d, J=9.0 Hz), 8.29 (1H, s), 7.89-8.00 (3H, m), 7.74 (2H, d, J=8.8 Hz), 7.51-7.65 (3H, m), 6.98 (2H, d, J=8.8 Hz), 4.44 (2H, s), 3.72 (2H, s), 3.21 (2H, t, J=6.1 Hz), 3.07 (4H, q, J=7.3 Hz), 2.74 (2H, t, J=6.1 Hz), 2.32 (3H, s), 1.20 (6H, t, J=7.3 Hz)

Mass spectrometric value (ESI-MS) 592, 594 (M−1) 618, 619 (M+23)

Compound 1001 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[3-(4-trifluoromethoxy-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl]-benzamide

The title compound 1001 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 8.30 (1H, s), 7.90-8.03 (4H, m), 7.58-7.64 (1H, m), 7.50-7.57 (1H, m), 7.32-7.38 (2H, m), 3.67 (2H, s), 2.88 (4H, bs), 2.72-2.82 (6H, m), 2.58-2.66 (2H, m), 2.29 (3H, s), 1.83-1.95 (4H, m), 1.09 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 628, 629, 630 (M−1)

Compound 1002 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-{3-[4-(2-hydroxy-ethoxy)-benzylidene-hydrazinocarbonyl]-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl}-benzamide

The title compound 1002 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 8.22 (1H, s), 7.70-8.00 (4H, m), 7.58-7.69 (1H, m), 7.50-7.57 (1H, m), 7.02 (2H, d, J=8.8 Hz), 4.10 (2H, t, J=4.6 Hz), 3.89 (2H, t, J=4.8 Hz), 3.67 (2H, s), 2.80-2.90 (4H, m), 2.66-2.78 (6H, m), 2.60 (2H, t, J=7.0 Hz), 2.28 (3H, s), 1.80-1.95 (4H, m), 1.08 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 604, 605, 606 (M−1)

Compound 1003 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-{3-[1-(3-fluoro-phenyl)-ethylidene-hydrazinocarbonyl]-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl}-benzamide

The title compound 1003 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 7.85-7.98 (2H, m), 7.68-7.80 (2H, m), 7.47-7.62 (2H, m), 7.40-7.47 (1H, m), 7.10-7.20 (1H, m), 3.66 (2H, s), 2.95 (2H, bs), 2.55-2.85 (10H, m), 2.35 (3H, s), 2.28 (3H, s), 1.87-1.93 (4H, m), 1.05 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 576, 577, 578 (M−1) 600, 601 (M+23)

Compound 1004 Quinoxaline-2-carboxylic acid [4-chloro-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-amide

The title compound 1004 was produced in substantially the same manner as in Example 1).

¹H-NMR (DMSO-d₆, 400 MHz): δ 12.65 (1H, s), 12.30 (1H, s), 9.61 (1H, s), 8.75 (1H, d, J=8.8 Hz), 8.47 (1H, s), 8.20-8.33 (2H, m), 8.00-8.10 (3H, m), 7.79 (1H, d, J=8.6 Hz), 7.50-7.67 (3H, m), 7.28-7.38 (1H, m)

Mass spectrometric value (ESI-MS) 446, 448 (M−1)

Compound 1005 Quinoxaline-2-carboxylic acid [4-chloro-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-amide

The title compound 1005 was produced in substantially the same manner as in Example 1).

¹H-NMR (CDCL₃, 400 MHz): δ 12.52 (1H, bs), 9.68 (1H, s), 9.46 (1H, bs), 8.70-8.80 (1H, bs), 8.12-8.20 (2H, m), 7.82-7.88 (3H, m), 7.40-7.70 (3H, m), 7.12 (1H, d, J=7.8 Hz), 2.26 (3H, s), 2.20 (3H, s)

Mass spectrometric value (ESI-MS) 456, 458 (M−1)

Compound 1006 Quinoxaline-2-carboxylic acid[4-chloro-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-amide

The title compound 1006 was produced in substantially the same manner as in Example 1).

¹H-NMR (DMSO-d₆, 400 MHz): δ 12.57 (1H, s), 12.44 (1H, s), 9.61 (1H, s), 8.73 (1H, d, J=8.8 Hz), 8.51 (1H, s), 8.20-8.32 (3H, m), 7.98-8.14 (4H, m), 7.85 (1H, d, J=8.5 Hz), 7.79 (1H, d, J=9.0 Hz)

Mass spectrometric value (ESI-MS) 530, 532 (M−1)

Compound 1007 N-[4-Chloro-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-3-(2,3-dihydroxy-propylsulfanylmethyl)-benzamide

The title compound 1007 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 8.64 (1H, d, J=8.8 Hz), 8.36 (1H, s), 7.97 (1H, s), 7.94 (1H, d, J=2.4 Hz), 7.87 (1H, d, J=7.8 Hz), 7.71 (1H, d, J=9.5 Hz), 7.60-7.66 (3H, m), 7.40-7.54 (2H, m), 7.15-7.25 (1H, m), 3.90 (2H, s), 3.70-3.80 (1H, m), 3.48-3.60 (2H, m), 2.64 (1H, dd, J=5.6 Hz, J=13.7 Hz), 2.51 (1H, dd, J=6.8 Hz, J=13.4 Hz)

Mass spectrometric value (ESI-MS) 514, 516 (M−1)

Compound 1008 N-[4-Chloro-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-(2,3-dihydroxy-propylsulfanylmethyl)-benzamide

The title compound 1008 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 8.65 (1H, d, J=9.0 Hz), 8.36 (1H, s), 7.97 (1H, s), 7.93 (1H, d, J=2.5 Hz), 7.87 (1H, d, J=7.6 Hz), 7.74 (2H, d, J=8.3 Hz), 7.62 (2H, dd, J=2.4 Hz, J=9.0 Hz), 7.51 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.27 (2H, d, J=8.1 Hz), 3.90 (2H, s), 3.70-3.80 (1H, m), 3.50-3.61 (2H, m), 2.63 (1H, dd, J=5.6 Hz, J=13.6 Hz), 2.50 (1H, dd, J=6.8 Hz, 13.6 Hz), 2.38 (3H, s)

Mass spectrometric value (ESI-MS) 510, 512, 513 (M−1)

Compound 1009 N-[4-Chloro-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-(2,3-dihydroxy-propylsulfanylmethyl)-benzamide

The title compound 1009 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 8.66 (1H, d, J=9.0 Hz), 8.31 (1H, s), 7.97 (1H, bs), 7.93 (1H, d, J=2.4 Hz), 7.87 (1H, bs), 7.60-7.69 (3H, m), 7.48-7.58 (2H, m), 7.15-7.25 (1H, m), 3.90 (2H, s), 3.70-3.80 (1H, m), 3.50-3.61 (2H, m), 2.63 (1H, dd, J=5.4 Hz, J=13.7 Hz), 2.50 (1H, dd, J=6.8 Hz, J=13.6 Hz), 2.32 (3H, s), 2.31 (3H, s)

Mass spectrometric value (ESI-MS) 524, 526, 529 (M−1)

Compound 1010 N-[4-Chloro-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-(2,3-dihydroxy-propylsulfanylmethyl)-benzamide

The title compound 1010 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 8.63 (1H, d, J=8.8 Hz), 8.39 (1H, s), 8.30-8.34 (1H, m), 8.08 (1H, d, J=8.3 Hz), 7.96 (1H, bs), 7.94 (1H, d, J=2.4 Hz), 7.85-7.90 (1H, m), 7.70 (1H, d, J=8.3 Hz), 7.60-7.67 (2H, m), 7.68-7.55 (1H, m), 3.89 (2H, s), 3.70-3.80 (1H, m), 3.48-3.60 (2H, m), 2.64 (1H, dd, J=5.6 Hz, J=13.7 Hz), 2.50 (1H, dd, J=7.1 Hz, J=13.7 Hz)

Mass spectrometric value (ESI-MS) 598, 600, 601, 603 (M−1)

Compound 1011 N-[4-Chloro-2-(4-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-3-(2,3-dihydroxy-propylsulfanylmethyl)-benzamide

The title compound 1011 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 8.66 (1H, d, J=9.0 Hz), 8.31 (1H, s), 7.95-7.98 (1H, m), 7.92 (1H, d, J=2.4 Hz), 7.86-7.90 (1H, m), 7.81 (2H, d, J=8.8 Hz), 7.60-7.65 (2H, m), 7.51 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.00 (2H, d, J=8.8 Hz), 3.90 (2H, s), 3.85 (3H, s), 3.70-3.80 (1H, m), 3.50-3.61 (2H, m), 2.63 (1H, dd, J=5.6 Hz, J=13.6 Hz), 2.51 (1H, dd, J=6.8 Hz, J=13.6 Hz)

Mass spectrometric value (ESI-MS) 529, 530, 531 (M−1)

Compound 1012 N-[4-Chloro-2-(4-trifluoromethoxy-benzylidene-hydrazinocarbonyl)-phenyl]-3-(2,3-dihydroxy-propylsulfanylmethyl)-benzamide

The title compound 1012 was produced in substantially the same manner as in Example 8.

¹H-NMR (CD₃OD, 400 MHz): δ 8.64 (1H, d, J=9.0 Hz), 8.39 (1H, s), 7.93-8.01 (4H, m), 7.85-7.90 (1H, m), 7.60-7.67 (2H, m), 7.51 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.36 (2H, d, J=8.1 Hz), 3.90 (2H, s), 3.70-3.80 (1H, m), 3.50-3.60 (2H, m), 2.63 (1H, dd, J=5.8 Hz, J=13.6 Hz), 2.51 (1H, dd, J=6.8 Hz, J=13.6 Hz)

Mass spectrometric value (ESI-MS) 580, 582, 583 (M−1)

Example Q

Compound 1013 3-(2,3-Dihydroxy-propylsulfanylmethyl)-N-[2-(3-fluoro-benzylidene-hydrazinocarbonyl)-4,5-bis-(2-methoxy-ethoxy)-phenyl]-benzamide

3,4-Dihydroxy-benzoic acid ethyl ester (compound A′) (2.0 g) was dissolved in acetone (20 ml). Potassium carbonate (4.3 g) and 1-bromo-2-methoxy-ethane (compound D) (5 ml) were added to the solution at room temperature, and the mixture was then stirred at 70° C. for 24 hr. After the completion of the reaction, the reaction solution was allowed to stand for cooling at room temperature, and the reaction system was concentrated under the reduced pressure. Distilled water was added to the residue, and the mixture was then subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure. The residue was purified by column chromatography using a hexane-acetone system to give 3,4-bis-(2-methoxy-ethoxy)-benzoic acid ethyl ester (3.06 g, yield 93%).

3,4-Bis-(2-methoxy-ethoxy)-benzoic acid ethyl ester (200 mg) produced by the above process was dissolved in acetic acid (200 μl). Fuming nitric acid (200 μl) was added dropwise to the solution at 0° C., and the mixture was then stirred at room temperature for one hr. After the completion of the reaction, the reaction system was added dropwise to distilled water (500 μl) cooled to 0° C., and the mixture was then neutralized with a saturated aqueous sodium hydrogencarbonate solution, and was further subjected to separatory extraction with ethyl acetate. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a hexane-acetone system to give 4,5-bis-(2-methoxy-ethoxy)-2-nitro-benzoic acid ethyl ester as a useful intermediate (220 mg, yield 96%).

Subsequently, 4,5-bis-(2-methoxy-ethoxy)-2-nitro-benzoic acid ethyl ester (3.0 mg) produced by the above process was dissolved in methanol, and platinum oxide (250 mg) was added to the solution at room temperature. The air in the reaction system was replaced by hydrogen, and the mixture was then stirred for one hr. After the completion of the reaction, the atmosphere in the reaction system was replaced by nitrogen. The reaction solution was filtered through Celite to remove platinum oxide. The filtrate was then concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a hexane-acetone system to give 2-amino-4,5-bis-(2-methoxy-ethoxy)-benzoic acid ethyl ester (compound A) (2.5 g, yield 92%).

2-Amino-4,5-bis-(2-methoxy-ethoxy)-benzoic acid ethyl ester (compound A) (2.5 g) produced by the above process was dissolved in anhydrous methylene chloride (40 ml). Pyridine (1.4 ml) and 3-(chloromethyl)-benzoyl chloride (compound B) (1.3 ml) were added dropwise to the solution at 0° C., and the mixture was stirred at room temperature for 30 min. After the completion of the reaction, distilled water was added thereto at room temperature, and the mixture was then subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure. The residue was purified by column chromatography using a hexane-acetone system to give 2-(3-chloromethylbenzoylamino)-4,5-bis-(2-methoxy-ethoxy)-benzoic acid ethyl ester (2.3 g, yield 62%).

Subsequently, 2-(3-chloromethyl-benzoylamino)-4,5-bis-(2-methoxy-ethoxy)-benzoic acid ethyl ester (1.1 g) was dissolved in anhydrous methylene chloride (20 ml). Triethylamine (800 μl) and 3-mercapto-1,2-propanediol (compound B′) (600 μl) were added dropwise to the solution at room temperature, and the mixture was stirred at that temperature for 36 hr. After the completion of the reaction, distilled water was added thereto at room temperature, and the mixture was then subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a chloroform-methanol system to give 2-[3-(2,3-dihydroxy-propylsulfanylmethyl)-benzoylamino]-4,5-bis-(2-methoxy-ethoxy)-benzoic acid ethyl ester (970 mg, yield 77%).

2-[3-(2,3-Dihydroxy-propylsulfanylmethyl)-benzoylamino]-4,5-bis-(2-methoxy-ethoxy)-benzoic acid ethyl ester (970 mg) produced by the above process was dissolved in ethanol (10 ml). Hydrazine monohydrate (1 ml) was added dropwise to the solution at room temperature, and the mixture was then stirred at that temperature for 36 hr. After the completion of the reaction, the reaction system was then concentrated under the reduced pressure, and the residue was purified by column chromatography eluted with a chloroform-methanol system to give 3-(2,3-dihydroxy-propylsulfanylmethyl)-N-[2-hydrazinocarbonyl-4,5-bis-(2-methoxy-ethoxy)-phenyl]-benzamide (780 mg, yield 83%).

Subsequently, 3-(2,3-dihydroxy-propylsulfanylmethyl)-N-[2-hydrazinocarbonyl-4,5-bis-(2-methoxy-ethoxy)-phenyl]-benzamide (55 mg) produced by the above process was dissolved in anhydrous toluene (1 ml), 3-fluorobenzaldehyde (compound C) (50 μl) was added dropwise to the solution at room temperature, and the mixture was then stirred at that temperature for one hr. After the completion of the reaction, the reaction system was concentrated under the reduced pressure, and the residue was purified by column chromatography eluted with a chloroform-methanol system to give the title compound 1013 (66 mg, yield 100%).

¹H-NMR (CDCL₃, 400 MHz): δ 12.00 (1H, bs), 10.14 (1H, bs), 8.50 (1H, s), 8.16 (1H, s), 7.93 (1H, d, J=7.6 Hz), 7.60-7.78 (2H, m), 7.24-7.57 (5H, m), 7.00-7.10 (1H, m), 4.20-4.28 (2H, m), 4.00-4.10 (3H, m), 3.80-3.88 (3H, m), 3.75-3.80 (2H, m), 3.60-3.72 (3H, m), 3.41 (3H, s), 3.38 (3H, s), 2.60 (2H, d, J=6.6 Hz)

Mass spectrometric value (ESI-MS) 628, 629 (M−1)

Compound 1014 N-[4,5-Bis-(2-methoxy-ethoxy)-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-(2,3-dihydroxy-propylsulfanylmethyl)-benzamide

The title compound 1014 was produced in substantially the same manner as in Example Q.

¹H-NMR (CDCL₃, 400 MHz): δ 12.06 (1H, bs), 9.84 (1H, bs), 8.54 (1H, s), 8.13 (1H, bs), 7.90-7.96 (2H, m), 7.77 (1H, s), 7.65-7.74 (2H, m), 7.45-7.55 (3H, m), 7.18 (1H, d, J=7.8 Hz), 4.22-4.28 (2H, m), 4.00-4.14 (3H, m), 3.80-3.85 (3H, m), 3.75-3.80 (2H, m), 3.62-3.70 (3H, m), 3.41 (3H, s), 3.40 (3H, s), 2.58 (2H, d, J=6.4 Hz), 2.34 (3H, s)

Mass spectrometric value (ESI-MS) 624, 625 (M−1)

Compound 1015 3-(2,3-Dihydroxy-propylsulfanylmethyl)-N-[2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-4,5-bis-(2-methoxy-ethoxy)-phenyl]-benzamide

The title compound 1015 was produced in substantially the same manner as in Example Q.

¹H-NMR (CDCL₃, 400 MHz): δ 12.08 (1H, bs), 9.95 (1H, bs), 8.53 (1H, s), 8.11 (1H, bs), 7.93 (1H, d, J=7.6 Hz), 7.76-7.83 (2H, m), 7.60 (1H, bs), 7.45-7.57 (3H, m), 7.11 (1H, d, J=7.8 Hz), 4.23-4.28 (2H, m), 4.07-4.12 (1H, m), 3.82-3.90 (3H, m), 3.75-3.80 (2H, m), 3.60-3.70 (3H, m), 3.41 (3H, s), 3.39 (3H, s), 2.59 (2H, d, J=6.6 Hz), 2.29 (2H, d, J=7.4 Hz), 2.24 (3H, s), 2.23 (3H, s)

Mass spectrometric value (ESI-MS) 638 (M−1)

Compound 1016 N-[2-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4,5-bis-(2-methoxy-ethoxy)-phenyl]-3-(2,3-dihydroxy-propylsulfanylmethyl)-benzamide

The title compound 1016 was produced in substantially the same manner as in Example Q.

¹H-NMR (CDCL₃, 400 MHz): δ 12.07 (1H, s), 10.69 (1H, s), 8.40 (1H, s), 8.15 (1H, s), 8.07 (1H, s), 7.93 (1H, d, J=7.1 Hz), 7.73-7.77 (1H, m), 7.71 (1H, s), 7.46-7.56 (2H, m), 7.38 (1H, d, J=8.3 Hz), 7.33 (1H, s), 4.60 (1H, bs), 4.18-4.23 (2H, m), 3.97-4.08 (3H, m), 3.74-3.95 (5H, m), 3.62-3.72 (1H, m), 3.58 (2H, t, J=9.0 Hz), 3.40 (3H, s), 3.37 (3H, s), 2.58-2.72 (2H, m)

Mass spectrometric value (ESI-MS) 712, 715 (M−1)

Example R

Compound 1017 3-(2,3-Dihydroxy-propylsulfanylmethyl)-N-[2-(3-fluoro-benzylidene-hydrazinocarbonyl)-4-methoxy-phenyl]-benzamide

5-Methoxy-2-nitro-benzoic acid (2.5 g) was dissolved in N,N-dimethylformamide (compound A′) (40 ml). Potassium carbonate (4.5 g) and methyl iodide (2.5 ml) were added to the solution at room temperature, and the mixture was then stirred at that temperature for 30 min. After the completion of the reaction, distilled water was added thereto at room temperature, and the mixture was then subjected to separatory extraction with ethyl acetate. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a hexane-acetone system to give 5-methoxy-2-nitrobenzoic acid methyl ester (2.7 g, yield 100%).

Subsequently, 5-methoxy-2-nitro-benzoic acid methyl ester (2.7 g) produced by the above process was dissolved in methanol (20 ml), and platinum oxide (180 mg) was added to the solution at room temperature. The air in the reaction system was replaced by hydrogen, the mixture was then stirred at that temperature for 5 hr. After the completion of the reaction, the atmosphere in the reaction system was replaced by nitrogen, and the reaction solution was then filtered through Celite to remove platinum oxide. The filtrate was then concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a hexane-acetone system to give 2-amino-5-methoxy-benzoic acid methyl ester (compound A) (2.2 g, yield 96%).

2-Amino-5-methoxy-benzoic acid methyl ester (compound A) (2.2 g) produced by the above process was dissolved in anhydrous methylene chloride (40 ml), pyridine (1.5 ml) and 3-(chloromethyl)benzoyl chloride (compound B) (2.1 ml) was added dropwise to the solution at 0° C., and the mixture was then stirred at room temperature for 15 min. After the completion of the reaction, distilled water was added thereto at room temperature, and the mixture was then subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure to precipitate crystals. The crude crystals were collected by Kiriyama Rohto and was washed with ether to give 2-(3-chloromethyl-benzoylamino)-5-methoxybenzoic acid methyl ester (3.0 g, yield 75%).

Subsequently, 2-(3-chloromethyl-benzoylamino)-5-methoxy-benzoic acid methyl ester (1.0 g) produced by the above process was dissolved in anhydrous methylene chloride (10 ml). Triethylamine (1 ml) and 3-mercapto-1,2-propanediol (compound B′) (1 ml) were added dropwise to the solution at room temperature, and the mixture was then stirred at that temperature for 36 hr. After the completion of the reaction, distilled water was added thereto at room temperature, and the mixture was then subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a chloroform-methanol system to give 2-[3-(2,3-dihydroxy-propanesulfanylmethyl)-benzoylamino]-5-methoxy-benzoic acid methyl ester as a useful intermediate (1.2 g, yield 100%).

2-[3-(2,3-Dihydroxy-propanesulfanylmethyl)-benzoylamino]-5-methoxybenzoic acid methyl ester (1.2 g) produced by the above process was dissolved in ethanol (20 ml). Hydrazine monohydrate (1.3 ml) was added dropwise to the solution at room temperature, and the mixture was then stirred at that temperature for 12 hr. After the completion of the reaction, the reaction system was then concentrated under the reduced pressure, and the residue was purified by column chromatography eluted with a chloroform-methanol system to give 3-(2,3-dihydroxy-propylsulfanylmethyl)-N-(2-hydrazinocarbonyl-4-methoxyphenyl)benzamide (840 mg, yield 65%).

Subsequently, 3-(2,3-dihydroxy-propylsulfanylmethyl)-N-(2-hydrazinocarbonyl-4-methoxy-phenyl)benzamide (61 mg) produced by the above process was dissolved in anhydrous toluene (1.5 ml). 3-Fluorobenzaldehyde (compound C) (50 μl) was added dropwise to the solution at room temperature, and the mixture was then stirred at 40° C. for 12 hr. After the completion of the reaction, the reaction system was concentrated under the reduced pressure, and the residue was purified by column chromatography eluted with a chloroform-methanol system to give the title compound 1017 (59 mg, 77%).

¹H-NMR (CD₃OD, 400 MHz): δ 8.42 (1H, d, J=9.3 Hz), 8.34 (1H, s), 7.95 (1H, s), 7.85 (1H, d, J=7.8 Hz), 7.70 (1H, d, J=10.2 Hz), 7.58-7.62 (2H, m), 7.40-7.52 (3H, m), 7.12-7.25 (2H, m), 3.90 (3H, s), 3.89 (2H, s), 3.70-3.78 (1H, m), 3.48-3.60 (2H, m), 2.63 (1H, dd, J=5.6 Hz, J=13.7 Hz), 2.50 (1H, dd, J=6.8 Hz, J=13.4 Hz)

Mass spectrometric value (ESI-MS) 510, 511 (M−1) 534 (M+23)

Compound 1018 3-(2,3-Dihydroxy-propylsulfanylmethyl)-N-[4-methoxy-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 1018 was produced in substantially the same manner as in Example R.

¹H-NMR (CD₃OD, 400 MHz): δ 8.44 (1H, d, J=9.0 Hz), 8.32 (1H, s), 7.95 (1H, s), 7.83-7.89 (1H, m), 7.74 (2H, d, J=8.1 Hz), 7.60 (1H, d, J=7.8 Hz), 7.49 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.41 (1H, d, J=2.9 Hz), 7.19-7.29 (3H, m), 3.90 (3H, s), 3.89 (2H, s), 3.70-3.78 (1H, m), 3.48-3.61 (2H, m), 2.63 (1H, dd, J=5.9 Hz, J=13.7 Hz), 2.50 (1H, dd, J=6.8 Hz, J=13.7 Hz), 2.38 (3H, s)

Mass spectrometric value (ESI-MS) 506, 507 (M−1)

Compound 1019 3-(2,3-Dihydroxy-propylsulfanylmethyl)-N-[2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-4-methoxy-phenyl]-benzamide

The title compound 1019 was produced in substantially the same manner as in Example R.

¹H-NMR (CD₃OD, 400 MHz): δ 8.44 (1H, d, J=9.0 Hz), 8.29 (1H, s), 7.95 (1H, s), 7.86 (1H, d, J=7.6 Hz), 7.66 (1H, s), 7.60 (1H, d, J=7.8 Hz), 7.54 (1H, d, J=7.3 Hz), 7.49 (1H, dd, J=7.9 Hz, J=7.9 Hz), 7.41 (1H, d, J=2.9 Hz), 7.15-7.25 (2H, m), 3.90 (3H, s), 3.89 (2H, s), 3.70-3.80 (1H, m), 3.49-3.60 (2H, m), 2.63 (1H, dd, J=5.6 Hz, J=13.7 Hz), 2.50 (1H, dd, J=7.1 Hz, J=13.7 Hz), 2.31 (3H, s), 2.30 (3H, s)

Mass spectrometric value (ESI-MS) 520 (M−1)

Compound 1020 N-[2-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-methoxy-phenyl]-3-(2,3-dihydroxy-propylsulfanyl-methyl)-benzamide

The title compound 1020 was produced in substantially the same manner as in Example R.

¹H-NMR (CD₃OD, 400 MHz): δ 8.41 (1H, d, J=9.3 Hz), 8.38 (1H, s), 8.32 (1H, bs), 8.05-8.15 (1H, m), 7.94 (1H, bs), 7.83-7.88 (1H, m), 7.69 (1H, d, J=8.3 Hz), 7.58-7.63 (1H, m), 7.47-7.52 (1H, m), 7.42 (1H, d, J=2.9 Hz), 7.20-7.25 (1H, m), 3.90 (3H, s), 3.89 (2H, s), 3.75-3.82 (1H, m), 3.45-3.60 (2H, m), 2.60-2.67 (1H, m), 2.45-2.54 (1H, m)

Mass spectrometric value (ESI-MS) 594, 596, 597 (M−1)

Compound 1021 3-(2,3-Dihydroxy-propylsulfanylmethyl)-N-[4-methoxy-2-(4-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 1021 was produced in substantially the same manner as in Example R.

¹H-NMR (CD₃OD, 400 MHz): δ 8.44 (1H, d, J=9.3 Hz), 8.29 (1H, s), 7.95 (1H, bs), 7.86 (1H, d, J=7.6 Hz), 7.80 (2H, d, J=8.8 Hz), 7.60 (1H, d, J=7.8 Hz), 7.49 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.40 (1H, d, J=2.9 Hz), 7.21 (1H, dd, J=2.9 Hz, J=9.3 Hz), 6.99 (2H, d, J=8.8 Hz), 3.90 (3H, s), 3.89 (2H, s), 3.85 (3H, s), 3.70-3.80 (1H, m), 3.49-3.60 (2H, m), 2.63 (1H, dd, J=5.6 Hz, J=13.7 Hz), 2.50 (1H, dd, J=7.1 Hz, J=13.4 Hz)

Mass spectrometric value (ESI-MS) 522, 523 (M−1)

Compound 1022 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[2-(3-fluoro-benzylidene-hydrazinocarbonyl)-4-methoxy-phenyl]-benzamide

The title compound 1022 was produced in substantially the same manner as in Example R.

¹H-NMR (CD₃OD, 400 MHz): δ 8.42 (1H, d, J=9.0 Hz), 8.36 (1H, s), 7.14-8.00 (10H, m), 3.90 (3H, s), 3.73 (2H, s), 3.25 (2H, t, J=6.0 Hz), 3.11 (4H, q, J=7.2 Hz), 2.75 (2H, t, J=5.9 Hz), 2.35 (3H, s), 1.23 (6H, t, J=7.3 Hz)

Mass spectrometric value (ESI-MS) 532, 533, 534 (M−1)

Compound 1023 N-[2-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-methoxy-phenyl]-3-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 1023 was produced in substantially the same manner as in Example R.

¹H-NMR (CD₃OD, 400 MHz): δ 8.36-8.42 (2H, m), 8.33 (1H, s), 8.03 (1H, d, J=8.5 Hz), 7.96 (1H, s), 7.89 (1H, d, J=7.8 Hz), 7.69 (1H, d, J=8.3 Hz), 7.59 (1H, d, J=7.8 Hz), 7.51 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.42 (1H, d, J=2.9 Hz), 7.22 (1H, dd, J=2.9 Hz, J=9.0 Hz), 3.90 (3H, s), 3.66 (2H, s), 2.70-2.77 (2H, m), 2.53-2.65 (6H, m), 2.28 (3H, s), 1.03 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 616, 618, 619 (M−1)

Compound 1024 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[4-methoxy-2-(4-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 1024 was produced in substantially the same manner as in Example R.

¹H-NMR (CD₃OD, 400 MHz): δ 8.43 (1H, d, J=9.3 Hz), 8.30 (1H, s), 7.97 (1H, bs), 7.90 (1H, d, J=8.6 Hz), 7.78 (2H, d, J=8.8 Hz), 7.58 (1H, d, J=7.8 Hz), 7.52 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.40 (1H, d, J=2.9 Hz), 7.20 (1H, dd, J=2.9 Hz, J=9.2 Hz), 6.99 (2H, d, J=8.8 Hz), 3.89 (3H, s), 3.84 (3H, s), 3.68 (2H, s), 2.85-2.92 (2H, m), 2.75 (4H, q, J=7.1 Hz), 2.62 (2H, t, J=7.0 Hz), 2.30 (3H, s), 1.08 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 544, 545, 546 (M−1)

Example S

Compound 1025 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[2-(3-fluoro-benzylidene-hydrazinocarbonyl)-4-(2-methoxy-ethoxy)-phenyl]-benzamide

5-Hydroxy-2-nitro-benzoic acid (compound A′) (1.5 g) was dissolved in methanol (15 ml). Thionyl chloride (1.5 ml) was added dropwise to the solution on an ice bath, and the mixture was then stirred at 80° C. for 12 hr. After the completion of the reaction, the reaction solution was neutralized with a saturated aqueous sodium hydrogencarbonate solution, and was then subjected to separatory extraction with ethyl acetate. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure to give crude 5-hydroxy-2-nitro-benzoic acid methyl ester (1.1 g, crude yield 70%).

Crude 5-hydroxy-2-nitro-benzoic acid methyl ester (1.1 g) produced by the above process was dissolved in acetone (12 ml). Potassium carbonate (1.5 g) and 1-bromo-2-methoxyethane (compound D) (1.5 ml) were added to the solution at room temperature, and the mixture was then stirred at 70° C. for 20 hr. After the completion of the reaction, the reaction system was concentrated under the reduced pressure. Distilled water was then added to the residue, and the mixture was then subjected to separatory extraction with ethyl acetate. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a hexane-acetone system to give 5-methoxy-ethoxy-2-nitro-benzoic acid methyl ester (1.0 g, yield 73%).

Subsequently, 5-methoxy-ethoxy-2-nitro-benzoic acid methyl ester (1.0 g) produced by the above process was dissolved in methanol (10 ml), and platinum oxide (90 mg) was added to the solution at room temperature. The air in the reaction system was replaced by hydrogen, and the mixture was then stirred at that temperature for 5 hr. After the completion of the reaction, the atmosphere in the reaction system was replaced by nitrogen, and the reaction solution was filtered through Celite to remove platinum oxide. The filtrate was then concentrated under the reduced pressure, and the residue was purified by column chromatography eluted with a hexane-ethyl acetate system to give 2-amino-5-methoxy-ethoxybenzoic acid methyl ester (compound A) as a useful intermediate (770 mg, yield 83%)

2-Amino-5-methoxy-ethoxybenzoic acid methyl ester (compound A) (770 mg) produced by the above process was dissolved in anhydrous methylene chloride (10 ml). Pyridine (500 μl) and 3-(chloromethyl)benzoyl chloride (compound B) (600 μl) were added dropwise to the solution at 0° C., and the mixture was then stirred at room temperature for 3 hr. After the completion of the reaction, distilled water was added thereto at room temperature, and the mixture was then subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure to precipitate crystals. The crude crystals were collected by Kiriyama Rohto and was washed with ether to give 2-(3-chloromethylbenzoylamino)-5-methoxy-ethoxybenzoic acid methyl ester (1.1 g, yield 89%).

Subsequently, 2-(3-chloromethylbenzoylamino)-5-methoxy-ethoxybenzoic acid methyl ester (1.1 g) produced by the above process was dissolved in anhydrous methylene chloride (15 ml). Triethylamine (1 ml) and N,N-diethyl-N′-methyl-ethylenediamine (compound B′) (900 μl) were added dropwise to the solution at room temperature, and the mixture was then stirred at that temperature for 12 hr. After the completion of the reaction, the reaction system was concentrated under the reduced pressure, and the residue was purified by column chromatography eluted with a chloroform-methanol system to give 2-(3-{[(2-diethylaminoethyl)-methylamino]-methyl}-benzoylamino)-5-(2-methoxy-ethoxy)-benzoic acid methyl ester as a useful intermediate (1.4 g, yield 100%).

2-(3-{[(2-Diethylamino-ethyl)-methylamino]-methyl}-benzoylamino)-5-(2-methoxy-ethoxy)-benzoic acid methyl ester (1.4 g) produced by the above process was dissolved in ethanol (15 ml). Hydrazine monohydrate (1.5 ml) was added dropwise to the solution at room temperature, and the mixture was then stirred at that temperature for 12 hr. After the completion of the reaction, the reaction system was concentrated under the reduced pressure, and the residue was purified by column chromatography eluted with a chloroform-methanol system to give 3-{[(2-dimethoxyamino-ethyl)-methyl-amino]-methyl}-N-[2-hydrazinocarbonyl-4-(2-methoxy-ethoxy)-phenyl]-benzamide (1.3 g, yield 89%).

Subsequently, 3-{[(2-dimethoxyamino-ethyl)-methyl-amino]-methyl}-N-[2-hydrazinocarbonyl-4-(2-methoxy-ethoxy)-phenyl]-benzamide (52 mg) produced by the above process was dissolved in anhydrous toluene (1 ml). 3-Fluorobenzaldehyde (compound C) (50 μl) was added dropwise to the solution at room temperature, and the mixture was then stirred at 40° C. for 3 hr. After the completion of the reaction, the reaction solution was allowed to cool at room temperature and was then purified by column chromatography eluted with a chloroform-methanol system to give the title compound 1025 (50 mg, yield 78%).

¹H-NMR (CD₃OD, 400 MHz): δ 8.43 (1H, d, J=9.0 Hz), 8.36 (1H, s), 7.99 (1H, s), 7.90-7.95 (1H, m), 7.68-7.76 (2H, m), 7.08-7.64 (6H, m), 4.20-4.25 (2H, m), 3.77-3.82 (2H, m), 3.73 (2H, s), 3.45 (3H, s), 3.18 (2H, t, J=6.1 Hz), 3.04 (4H, q, J=7.2 Hz), 2.73 (2H, t, J=6.1 Hz), 2.34 (3H, s), 1.20 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 576, 577, 578 (M−1)

Compound 1026 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[4-(2-methoxy-ethoxy)-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 1026 was produced in substantially the same manner as in Example S.

¹H-NMR (CD₃OD, 400 MHz): δ 8.43 (1H, d, J=9.0 Hz), 8.32 (1H, s), 7.97 (1H, s), 7.89-7.94 (1H, m), 7.73 (2H, d, J=8.0 Hz), 7.59 (1H, d, J=7.3 Hz), 7.52 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.43 (1H, d, J=2.9 Hz), 7.21-7.30 (3H, m), 4.20-4.25 (2H, m), 3.76-3.81 (2H, m), 3.68 (2H, s), 3.45 (3H, s), 2.58-2.90 (8H, m), 2.38 (3H, s), 2.30 (3H, s), 1.07 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 572, 573, 574 (M−1)

Compound 1027 N-[2-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-(2-methoxy-ethoxy)-phenyl]-3-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 1027 was produced in substantially the same manner as in Example S.

¹H-NMR (CD₃OD, 400 MHz): δ 8.41 (1H, d, J=9.3 Hz), 8.38 (1H, s), 8.33 (1H, s), 8.03 (1H, d, J=8.3 Hz), 7.96 (1H, s), 7.88-7.92 (1H, m), 7.68 (1H, d, J=8.3 Hz), 7.59 (1H, d, J=7.8 Hz), 7.52 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.44 (1H, d, J=2.9 Hz), 7.24 (1H, dd, J=2.9 Hz, J=9.0 Hz), 4.20-4.25 (2H, m), 3.76-3.80 (2H, m), 3.67 (2H, s), 3.44 (3H, s), 2.81 (2H, t, J=6.8 Hz), 2.68 (4H, q, J=7.2 Hz), 2.59 (2H, t, J=7.1 Hz), 2.29 (3H, s), 1.06 (6H, t, J=7.3 Hz)

Mass spectrometric value (ESI-MS) 660, 662, 663 (M−1) 684 (M+23)

Compound 1028 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[2-(3-fluoro-benzylidene-hydrazinocarbonyl)-4,5-bis-(2-methoxy-ethoxy)-phenyl]-benzamide

The title compound 1028 was produced in substantially the same manner as in Example Q.

¹H-NMR (CD₃OD, 400 MHz): δ 8.49 (1H, bs), 8.37 (1H, bs), 8.00 (1H, bs), 7.95 (1H, d, J=7.3 Hz), 7.85-7.90 (1H, m), 7.40-7.76 (5H, m), 7.12-7.24 (1H, m), 4.22-4.32 (4H, m), 3.76-3.86 (4H, m), 3.72 (2H, s), 3.46 (3H, s), 3.46 (3H, s), 3.00-3.08 (2H, m), 2.82-2.96 (4H, m), 2.65-2.73 (2H, m), 2.33 (3H, s), 1.12-1.20 (6H, m)

Mass spectrometric value (ESI-MS) 650, 651, 652 (M−1) 672, 675 (M+23)

Compound 1029 N-[4,5-Bis-(2-methoxy-ethoxy)-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 1029 was produced in substantially the same manner as in Example Q.

¹H-NMR (CD₃OD, 400 MHz): δ 8.49 (1H, s), 8.34 (1H, s), 8.00 (1H, s), 7.92-7.98 (1H, m), 7.74 (2H, d, J=8.0 Hz), 7.51-7.65 (3H, m), 7.27 (2H, d, J=8.3 Hz), 4.23-4.33 (4H, m), 3.77-3.87 (4H, m), 3.71 (2H, s), 3.46 (3H, s), 3.46 (3H, s), 2.60-3.00 (8H, m), 2.39 (3H, s), 2.32 (3H, s), 1.10 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 646, 647, 648 (M−1)

Compound 1030 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-4,5-bis-(2-methoxy-ethoxy)-phenyl]-benzamide

The title compound 1030 was produced in substantially the same manner as in Example Q.

¹H-NMR (CD₃OD, 400 MHz): δ 8.48 (1H, s), 8.31 (1H, s), 8.01 (1H, s), 7.95 (1H, d, J=7.3 Hz), 7.40-7.70 (5H, m), 7.18-7.23 (1H, m), 4.23-4.32 (4H, m), 3.76-3.86 (4H, m), 3.72 (2H, s), 3.45-3.80 (6H, m), 2.95-3.05 (2H, m), 2.80-2.90 (4H, m), 2.67 (2H, t, J=6.7 Hz), 2.26-2.34 (9H, m), 1.12 (6H, t, J=7.3 Hz)

Mass spectrometric value (ESI-MS) 660, 661, 662 (M−1)

Compound 1031 N-[2-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4,5-bis-(2-methoxy-ethoxy)-phenyl]-3-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 1031 was produced in substantially the same manner as in Example Q.

¹H-NMR (CD₃OD, 400 MHz): δ 7.40-8.50 (10H, m), 4.23-4.33 (4H, m), 3.77-3.88 (4H, m), 3.74 (2H, s), 3.45-3.48 (6H, m), 2.65-3.30 (8H, m), 2.35 (3H, s), 1.21 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 734, 736, 737 (M−1)

Compound 1032 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[2-(4-methoxy-benzylidene-hydrazinocarbonyl)-4,5-bis-(2-methoxy-ethoxy)-phenyl]-benzamide

The title compound 1032 was produced in substantially the same manner as in Example Q.

¹H-NMR (CD₃OD, 400 MHz): δ 8.48 (1H, s), 8.32 (1H, s), 8.01 (1H, s), 7.95 (1H, d, J=7.3 Hz), 7.79 (2H, d, J=8.8 Hz), 7.50-7.70 (3H, m), 7.00 (2H, d, J=8.8 Hz), 4.23-4.33 (4H, m), 3.76-3.88 (7H, m), 3.72 (2H, s), 3.45-3.48 (6H, m), 3.05-3.10 (2H, m), 2.90-3.00 (4H, m), 2.65-2.73 (2H, m), 2.33 (3H, s), 1.16 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 662, 663, 664 (M−1)

Compound 1033 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-{2-(3-fluoro-benzylidene-hydrazinocarbonyl)-4-[2-(2-methoxy-ethoxy)-ethoxy]-phenyl}-benzamide

The title compound 1033 was produced in substantially the same manner as in Example S.

¹H-NMR (CDCL₃, 400 MHz): δ 11.36 (1H, bs), 8.48 (1H, bs), 8.21 (1H, s), 7.65-7.93 (6H, m), 7.10-7.38 (5H, m), 4.12 (2H, bs), 3.78 (2H, bs), 3.63-3.67 (4H, m), 3.56-3.62 (2H, m), 3.50-3.55 (2H, m), 3.28 (3H, s), 3.05 (4H, bs), 2.75-2.80 (2H, m), 2.20-2.40 (3H, m), 1.15-1.25 (6H, m)

Mass spectrometric value (ESI-MS) 620, 621, 622 (M−1)

Compound 1034 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[4-[2-(2-methoxy-ethoxy)-ethoxy]-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 1034 was produced in substantially the same manner as in Example S.

¹H-NMR (CDCL₃, 400 MHz): δ 11.37 (1H, bs), 8.49 (1H, d, J=9.0 Hz), 8.20 (1H, s), 7.84-7.90 (2H, m), 7.80 (1H, d, J=7.6 Hz), 7.60 (2H, d, J=7.8 Hz), 7.20-7.46 (3H, m), 6.98-7.20 (3H, m), 4.05-4.10 (2H, m), 3.68-3.74 (2H, m), 3.61-3.65 (2H, m), 3.50-3.55 (4H, m), 3.28 (3H, s), 2.50-2.70 (8H, m), 2.30 (3H, s), 2.17 (3H, s), 0.95-1.04 (6H, m)

Mass spectrometric value (ESI-MS) 616, 617, 618 (M−1)

Compound 1035 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-{2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-4-[2-(2-methoxy-ethoxy)-ethoxy]-phenyl}-benzamide

The title compound 1035 was produced in substantially the same manner as in Example S.

¹H-NMR (CDCL₃, 400 MHz): δ 11.37 (1H, bs), 8.48 (1H, d, J=9.0 Hz), 8.19 (1H, s), 7.86 (1H, s), 7.80 (1H, d, J=7.6 Hz), 7.54 (1H, s), 7.20-7.46 (4H, m), 6.96-7.12 (3H, m), 4.03-4.10 (2H, m), 3.69 (2H, bs), 3.60-3.65 (2H, m), 3.50-3.55 (4H, m), 3.27 (3H, s), 2.47-2.70 (8H, m), 2.21 (6H, s), 2.16 (3H, s), 0.98 (6H, t, J=7.0 Hz)

Mass spectrometric value (ESI-MS) 630, 631, 632 (M−1)

Compound 1036 N-{2-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-[2-(2-methoxy-ethoxy)-ethoxy]-phenyl}-3-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 1036 was produced in substantially the same manner as in Example S.

¹H-NMR (CD₃OD, 400 MHz): δ 8.41 (1H, d, J=9.0 Hz), 8.38 (1H, s), 8.32 (1H, s), 8.03 (1H, d, J=8.3 Hz), 7.96 (1H, s), 7.87-7.92 (1H, m), 7.68 (1H, d, J=8.3 Hz), 7.59 (1H, d, J=7.8 Hz), 7.44-7.54 (2H, m), 7.24 (1H, dd, J=2.9 Hz, J=9.0 Hz), 4.20-4.26 (2H, m), 3.84-3.90 (2H, m), 3.68-3.74 (2H, m), 3.66 (2H, s), 3.55-3.60 (2H, m), 3.37 (3H, s), 2.53-2.75 (8H, m), 2.28 (3H, s), 1.03 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 704, 706, 707 (M−1)

Compound 1037 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-{2-(4-methoxy-benzylidene-hydrazinocarbonyl)-4-[2-(2-methoxy-ethoxy)-ethoxy]-phenyl}-benzamide

The title compound 1037 was produced in substantially the same manner as in Example S.

¹H-NMR (CD₃OD, 400 MHz): δ 8.44 (1H, d, J=9.3 Hz), 8.29 (1H, s), 7.96 (1H, bs), 7.87-7.92 (1H, m), 7.78 (2H, d, J=8.8 Hz), 7.58 (1H, d, J=7.6 Hz), 7.51 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.43 (1H, d, J=2.9 Hz), 7.22 (1H, dd, J=2.9 Hz, J=9.0 Hz), 6.99 (2H, d, J=9.0 Hz), 4.21-4.25 (2H, m), 3.85-3.88 (2H, m), 3.84 (3H, s), 3.69-3.72 (2H, m), 3.67 (2H, s), 3.56-3.59 (2H, m), 3.37 (3H, s), 2.55-2.80 (8H, m), 2.28 (3H, s), 1.04 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 632, 633, 634 (M−1)

Example T

Compound 1038 N-[2-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-(3-piperidin-1-yl-propoxy)-phenyl]-3-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-benzamide

5-Hydroxy-2-nitro-benzoic acid (compound A′) (2.0 g) was dissolved in methanol (30 ml). Thionyl chloride (3.0 ml) was added dropwise to the solution on an ice bath, and the mixture was then stirred at 75° C. for 96 hr. After the completion of the reaction, the reaction solution was neutralized with a saturated aqueous sodium hydrogencarbonate solution and was then subjected to separatory extraction with ethyl acetate. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure to give crude 5-hydroxy-2-nitro-benzoic acid methyl ester (2.2 g, crude yield 100%).

Subsequently, crude 5-hydroxy-2-nitro-benzoic acid methyl ester (2.2 g) produced by the above process was dissolved in acetone (15 ml). Potassium carbonate (3.0 g) and 1-bromo-3-chloro-propane (compound D) (3.1 ml) were added to the solution at room temperature, and the mixture was then stirred at that temperature for 2 hr. After the completion of the reaction, the reaction system was concentrated under the reduced pressure. Distilled water was then added to the residue, the mixture was subjected to separatory extraction with chloroform, and the organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a hexane-acetone system to give 5-(3-chloro-propoxy)-2-nitro-benzoic acid methyl ester (2.9 g, yield 96%).

5-(3-Chloro-propoxy)-2-nitro-benzoic acid methyl ester (2.9 g) produced by the above process was dissolved in acetone (30 ml). Potassium carbonate (3.0 g) and piperidine (compound E) (2.0 ml) were added to the solution at room temperature, and the mixture was then stirred at 70° C. for 24 hr. After the completion of the reaction, the reaction system was concentrated under the reduced pressure. Distilled water was then added to the residue, the mixture was subjected to separatory extraction with chloroform, and the organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a chloroform-methanol system to give 2-nitro-5-(3-piperidin-1-yl-propoxy)-benzoic acid methyl ester (2.4 g, yield 69%).

Subsequently, 2-nitro-5-(3-piperidin-1-yl-propoxy)-benzoic acid methyl ester (2.4 g) produced by the above process was dissolved in methanol (24 ml), and platinum oxide (220 mg) was added to the solution at room temperature. The air in the reaction system was replaced by hydrogen, and the mixture was then stirred at that temperature for 12 hr. After the completion of the reaction, the atmosphere in the reaction system was replaced by nitrogen, and the reaction solution was filtered through Celite to remove platinum oxide. The filtrate was then concentrated under the reduced pressure, and the residue was purified by column chromatography eluted with a chloroform-methanol system to give 2-amino-5-(3-piperidin-1-yl-propoxy)-benzoic acid methyl ester (compound A) as a useful intermediate (1.1 g, yield 50%).

2-Amino-5-(3-piperidin-1-yl-propoxy)-benzoic acid methyl ester (compound A) (1.1 g) produced by the above process was dissolved in anhydrous methylene chloride (12 ml). Pyridine (600 μl) and 3-(chloromethyl)benzoyl chloride (compound B) (600 μl) were added dropwise to the solution at 0° C., and the mixture was stirred at room temperature for one hr. After the completion of the reaction, distilled water was added thereto at room temperature, and the mixture was then subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a chloroform-methanol system to give 2-(3-chloromethyl-benzoylamino)-5-(3-piperidin-1-yl-propoxy)-benzoic acid methyl ester (1.5 g, yield 93%).

Subsequently, 2-(3-chloromethyl-benzoylamino)-5-(3-piperidin-1-yl-propoxy)-benzoic acid methyl ester (1.5 g) produced by the above process was dissolved in anhydrous methylene chloride (11 ml). Triethylamine (450 μl) and N,N-diethyl-N′-methyl-ethylenediamine (compound B′) (480 μl) was added dropwise to the solution at room temperature, and the mixture was then stirred at that temperature for 12 hr. After the completion of the reaction, the reaction system was concentrated under the reduced pressure, and the residue was purified by column chromatography eluted with a chloroform-methanol system to give 2-(3-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}benzoylamino)-5-(3-piperidin-1-yl-propoxy)-benzoic acid methyl ester as a useful intermediate (290 mg, yield 34%).

2-(3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}benzoyl-amino)-5-(3-piperidin-1-yl-propoxy)-benzoic acid methyl ester (290 mg) produced by the above process was dissolved in ethanol (4 ml). Hydrazine monohydrate (300 μl) was added dropwise to the solution at room temperature, and the mixture was then stirred at that temperature for 6 hr. After the completion of the reaction, the reaction system was concentrated under the reduced pressure, and the residue was purified by column chromatography eluted with a chloroform-methanol system to give 3-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-N-[2-hydrazinocarbonyl-4-(3-piperidin-1-yl-propoxy)-phenyl]-benzamide (140 mg, yield 49%).

Subsequently, 3-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-N-[2-hydrazinocarbonyl-4-(3-piperidin-1-yl-propoxy)-phenyl]-benzamide (50 mg) produced by the above process was dissolved in anhydrous toluene (1.2 ml). 4-Chloro-3-(trifluoromethyl)benzaldehyde (compound C) (50 μl) was added dropwise to the solution at room temperature, and the mixture was then stirred at that temperature for 12 hr. After the completion of the reaction, the reaction system was concentrated. The residue was purified by column chromatography eluted with a chloroform-methanol system to give the title compound 1038 (67 mg, yield 100%).

¹H-NMR (CD₃OD, 400 MHz): δ 8.40 (1H, d, J=9.0 Hz), 8.37 (1H, s), 8.32 (1H, s), 8.03 (1H, d, J=8.5 Hz), 7.95 (1H, s), 7.85-7.94 (1H, m), 7.68 (1H, d, J=8.3 Hz), 7.56-7.63 (1H, m), 7.51 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.44 (1H, d, J=2.7 Hz), 7.20 (1H, dd, J=2.7 Hz, J=9.0 Hz), 4.08-4.15 (2H, m), 3.62-3.70 (2H, m), 2.45-2.72 (14H, m), 2.27 (3H, s), 1.98-2.07 (2H, m), 1.60-1.70 (4H, m), 1.45-1.54 (2H, m), 1.01 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 727, 728, 730 (M−1)

Compound 1039 N-[2-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-(3-piperidin-1-yl-propoxy)-phenyl]-3-(2-hydroxy-ethylsulfanylmethyl)-benzamide

The title compound 1039 was produced in substantially the same manner as in Example T.

¹H-NMR (CD₃OD, 400 MHz): δ 8.41 (1H, d, J=9.0 Hz), 8.37 (1H, s), 8.30-8.34 (1H, m), 8.04 (1H, d, J=7.1 Hz), 7.83-7.94 (2H, m), 7.68 (1H, d, J=8.3 Hz), 7.59 (1H, d, J=7.6 Hz), 7.50 (1H, dd, J=7.8 Hz, J=7.8 Hz), 7.42 (1H, d, J=2.7 Hz), 7.22 (1H, dd, J=2.7 Hz, J=9.2 Hz), 4.14 (2H, t, J=6.1 Hz), 3.86 (2H, s), 3.68 (2H, t, J=6.8 Hz), 2.65-2.80 (6H, m), 2.57 (2H, t, J=6.8 Hz), 2.05-2.15 (2H, m), 1.67-1.75 (4H, m), 1.50-1.60 (2H, m)

Mass spectrometric value (ESI-MS) 675, 677, 678 (M−1)

Compound 1040 3-(2-Hydroxy-ethylsulfanylmethyl)-N-[2-(4-methoxy-benzylidene-hydrazinocarbonyl)-4-(3-piperidin-1-yl-propoxy)-phenyl]-benzamide

The title compound 1040 was produced in substantially the same manner as in Example T.

¹H-NMR (CD₃OD, 400 MHz): δ 8.45 (1H, d, J=9.0 Hz), 8.28 (1H, s), 7.92 (1H, bs), 7.85 (1H, d, J=8.0 Hz), 7.78 (2H, d, J=8.3 Hz), 7.58 (1H, d, J=7.8 Hz), 7.49 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.39 (1H, d, J=2.4 Hz), 7.18 (1H, d, J=9.3 Hz), 6.98 (2H, d, J=8.3 Hz), 4.11 (2H, t, J=5.7 Hz), 3.86 (2H, s), 3.83 (3H, s), 3.68 (2H, t, J=6.8 Hz), 2.54-2.68 (8H, m), 2.00-2.09 (2H, m), 1.62-1.70 (4H, m), 1.47-1.57 (2H, m)

Mass spectrometric value (ESI-MS) 603, 604, 605 (M−1)

Compound 1041 N-[2-(3,4-Dimethyl-benzylidene-hydrazinocarbonyl)-4-(3-piperidin-1-yl-propoxy)-phenyl]-3-(2-hydroxy-ethylsulfanylmethyl)-benzamide

The title compound 1041 was produced in substantially the same manner as in Example T.

¹H-NMR (CD₃OD, 400 MHz): δ 8.45 (1H, d, J=9.3 Hz), 8.28 (1H, s), 7.93 (1H, bs), 7.86 (1H, d, J=7.8 Hz), 7.65 (1H, s), 7.59 (1H, d, J=7.8 Hz), 7.53 (1H, d, J=8.1 Hz), 7.49 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.41 (1H, d, J=2.7 Hz), 7.16-7.23 (2H, m), 4.13 (2H, t, J=6.1 Hz), 3.87 (2H, s), 3.68 (2H, t, J=6.8 Hz), 2.55-2.73 (8H, m), 2.31 (3H, s), 2.30 (3H, s), 2.00-2.10 (2H, m), 1.65-1.75 (4H, m), 1.50-1.58 (2H, m)

Mass spectrometric value (ESI-MS) 601, 602, 603 (M−1)

Compound 1042 3-(2-Hydroxy-ethylsulfanylmethyl)-N-[2-(4-methyl-benzylidene-hydrazinocarbonyl)-4-(2-piperidin-1-yl-ethoxy)-phenyl]-benzamide

The title compound 1042 was produced in substantially the same manner as in Example T.

¹H-NMR (CD₃OD, 400 MHz): δ 8.46 (1H, d, J=9.0 Hz), 8.32 (1H, s), 7.93 (1H, bs), 7.86 (1H, d, J=7.8 Hz), 7.73 (2H, d, J=8.3 Hz), 7.59 (1H, d, J=7.8 Hz), 7.49 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.42 (1H, d, J=2.9 Hz), 7.25 (2H, d, J=7.8 Hz), 7.22 (1H, dd, J=2.9 Hz, J=9.3 Hz), 4.23 (2H, t, J=5.6 Hz), 3.87 (2H, s), 3.68 (2H, t, J=6.8 Hz), 2.83 (2H, t, J=5.7 Hz), 2.55-2.65 (6H, m), 2.38 (3H, s), 1.62-1.70 (4H, m), 1.46-1.55 (2H, m)

Mass spectrometric value (ESI-MS) 573, 574, 575 (M−1)

Compound 1043 N-[2-(3,4-Dimethyl-benzylidene-hydrazinocarbonyl)-4-(2-piperidin-1-yl-ethoxy)-phenyl]-3-(2-hydroxy-ethylsulfanylmethyl)-benzamide

The title compound 1043 was produced in substantially the same manner as in Example T.

¹H-NMR (CD₃OD, 400 MHz): δ 8.46 (1H, d, J=9.0 Hz), 8.29 (1H, s), 7.93 (1H, s), 7.86 (1H, d, J=7.6 Hz), 7.66 (1H, s), 7.60 (1H, d, J=7.6 Hz), 7.54 (1H, d, J=8.0 Hz), 7.50 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.43 (1H, d, J=3.0 Hz), 7.17-7.25 (2H, m), 4.23 (2H, t, J=5.6 Hz), 3.87 (2H, s), 3.68 (2H, t, J=6.7 Hz), 2.83 (2H, t, J=5.5 Hz), 2.55-2.65 (6H, m), 2.32 (3H, s), 2.30 (3H, s), 1.61-1.70 (4H, m), 1.45-1.55 (2H, m)

Mass spectrometric value (ESI-MS) 587, 588 (M−1)

Compound 1044 N-[2-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-(2-piperidin-1-yl-ethoxy)-phenyl]-3-(2-hydroxy-ethylsulfanylmethyl)-benzamide

The title compound 1044 was produced in substantially the same manner as in Example T.

¹H-NMR (CD₃OD, 400 MHz): δ 8.44 (1H, d, J=9.0 Hz), 8.38 (1H, s), 8.34 (1H, bs), 8.03-8.08 (1H, m), 7.93 (1H, bs), 7.86 (1H, d, J=7.8 Hz), 7.69 (1H, d, J=8.3 Hz), 7.60 (1H, d, J=8.6 Hz), 7.50 (1H, dd, J=7.8 Hz, J=7.8 Hz), 7.44 (1H, d, J=2.7 Hz), 7.24 (1H, dd, J=2.9 Hz, J=9.3 Hz), 4.23 (2H, t, J=5.6 Hz), 3.86 (2H, s), 3.68 (2H, t, J=7.0 Hz), 2.83 (2H, t, J=5.6 Hz), 2.55-2.63 (6H, m), 1.62-1.70 (4H, m), 1.45-1.55 (2H, m)

Mass spectrometric value (ESI-MS) 661, 663, 664 (M−1)

Compound 1045 3-(2-Hydroxy-ethylsulfanylmethyl)-N-[2-(4-methoxy-benzylidene-hydrazinocarbonyl)-4-(2-piperidin-1-yl-ethoxy)-phenyl]-benzamide

The title compound 1045 was produced in substantially the same manner as in Example T.

¹H-NMR (CD₃OD, 400 MHz): δ 8.47 (1H, d, J=9.3 Hz), 8.30 (1H, s), 7.93 (1H, bs), 7.86 (1H, d, J=8.1 Hz), 7.80 (2H, d, J=8.8 Hz), 7.60 (1H, d, J=7.8 Hz), 7.50 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.42 (1H, d, J=2.9 Hz), 7.22 (1H, dd, J=2.9 Hz, J=9.0 Hz), 6.99 (2H, d, J=8.8 Hz), 4.23 (2H, t, J=5.6 Hz), 3.87 (2H, s), 3.84 (3H, s), 3.68 (2H, t, J=6.8 Hz), 2.82 (2H, t, J=5.6 Hz), 2.55-2.63 (6H, m), 1.62-1.70 (4H, m), 1.45-1.55 (2H, m)

Mass spectrometric value (ESI-MS) 589, 590 (M−1)

Compound 1046 N-[4-Cyclohexylmethoxy-2-(3-fluoro-benzylidene-hydrazinocarbonyl)-phenyl]-3-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 1046 was produced in substantially the same manner as in Example S.

¹H-NMR (CD₃OD, 400 MHz): δ 8.41 (1H, d, J=9.0 Hz), 8.34 (1H, s), 7.97 (1H, s), 7.88-7.93 (1H, m), 7.68-7.78 (1H, m), 7.30-7.64 (5H, m), 7.08-7.22 (2H, m), 3.88 (2H, d, J=6.1 Hz), 3.69 (2H, s), 2.80-2.93 (2H, m), 2.68-2.80 (4H, m), 2.55-2.65 (2H, m), 2.30 (3H, s), 1.68-1.95 (5H, m), 1.10-1.42 (6H, m), 1.08 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 614, 615, 616 (M−1) 638 (M+23)

Compound 1047 N-[4-Cyclohexylmethoxy-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 1047 was produced in substantially the same manner as in Example S.

¹H-NMR (CD₃OD, 400 MHz): δ 8.41 (1H, d, J=9.0 Hz), 8.32 (1H, s), 7.96 (1H, bs), 7.88-7.92 (1H, m), 7.73 (2H, d, J=8.0 Hz), 7.58 (1H, d, J=7.6 Hz), 7.52 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.39 (1H, d, J=2.8 Hz), 7.26 (2H, d, J=8.1 Hz), 7.19 (1H, dd, J=2.9 Hz, J=9.0 Hz), 3.88 (2H, d, J=6.4 Hz), 3.68 (2H, s), 2.55-2.85 (8H, m), 2.38 (3H, s), 2.29 (3H, s), 1.70-1.95 (5H, m), 1.10-1.42 (6H, m), 1.05 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 610, 611, 612 (M−1)

Compound 1048 N-[4-Cyclohexylmethoxy-2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 1048 was produced in substantially the same manner as in Example S.

¹H-NMR (CD₃OD, 400 MHz): δ 8.42 (1H, d, J=9.3 Hz), 8.28 (1H, s), 7.96 (1H, bs), 7.88-7.93 (1H, m), 7.64 (1H, s), 7.58 (1H, d, J=7.6 Hz), 7.49-7.55 (2H, m), 7.39 (1H, d, J=2.9 Hz), 7.16-7.23 (2H, m), 3.87 (2H, d, J=6.4 Hz), 3.67 (2H, s), 2.55-2.80 (8H, m), 2.31 (3H, s), 2.30 (3H, s), 2.29 (3H, s), 1.70-1.95 (5H, m), 1.10-1.42 (6H, m), 1.04 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 624, 625, 626 (M−1) 670, 671 (M+23×2)

Compound 1049 N-[2-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-cyclohexylmethoxy-phenyl]-3-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 1049 was produced in substantially the same manner as in Example S.

¹H-NMR (CD₃OD, 400 MHz): δ 8.30-8.42 (2H, m), 8.03 (1H, d, J=8.3 Hz), 7.96 (1H, s), 7.87-7.92 (1H, m), 7.69 (1H, d, J=8.6 Hz), 7.59 (1H, d, J=7.6 Hz), 7.48-7.54 (2H, m), 7.41 (1H, d, J=2.7 Hz), 7.20 (1H, dd, J=2.7 Hz, J=9.0 Hz), 3.88 (2H, d, J=6.3 Hz), 3.67 (2H, s), 2.54-2.78 (8H, m), 2.28 (3H, s), 1.70-1.95 (5H, m), 1.08-1.42 (6H, m), 1.04 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 698, 700, 701 (M−1)

Compound 1050 N-[4-Cyclohexylmethoxy-2-(4-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-3-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 1050 was produced in substantially the same manner as in Example S.

¹H-NMR (CD₃OD, 400 MHz): δ 8.42 (1H, d, J=9.0 Hz), 8.29 (1H, s), 7.96 (1H, bs), 7.87-7.93 (1H, m), 7.78 (2H, d, J=8.8 Hz), 7.59 (1H, d, J=7.3 Hz), 7.51 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.38 (1H, d, J=3.0 Hz), 7.18 (1H, dd, J=3.0 Hz, J=9.3 Hz), 6.99 (2H, d, J=8.8 Hz), 3.87 (2H, d, J=6.4 Hz), 3.84 (3H, s), 3.67 (2H, s), 2.54-2.80 (8H, m), 2.28 (3H, s), 1.70-1.95 (5H, m), 1.10-1.42 (6H, m), 1.03 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 626, 627, 628 (M−1) 650 (M+23)

Compound 1051 N-[2-(3-Fluoro-benzylidene-hydrazinocarbonyl)-4-(4-fluoro-butoxy)-phenyl]-3-(2-hydroxy-ethylsulfanylmethyl)-benzamide

The title compound 1051 was produced in substantially the same manner as in Example S.

¹H-NMR (CD₃OD, 400 MHz): δ 8.43 (1H, d, J=9.0 Hz), 8.34 (1H, s), 7.93 (1H, s), 7.86 (1H, d, J=7.8 Hz), 7.70 (1H, d, J=9.0 Hz), 7.59 (2H, d, J=7.6 Hz), 7.40-7.52 (3H, m), 7.13-7.25 (2H, m), 4.55-4.60 (1H, m), 4.46 (1H, t, J=5.7 Hz), 4.13 (2H, t, J=5.9 Hz), 3.87 (2H, s), 3.68 (2H, t, J=6.8 Hz), 2.58 (2H, t, J=6.8 Hz), 1.80-1.95 (4H, m)

Mass spectrometric value (ESI-MS) 540, 541 (M−1) 564 (M+23)

Compound 1052 N-[4-(4-Fluoro-butoxy)-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-(2-hydroxy-ethylsulfanylmethyl)-benzamide

The title compound 1052 was produced in substantially the same manner as in Example S.

¹H-NMR (CD₃OD, 400 MHz): δ 8.45 (1H, d, J=9.0 Hz), 8.31 (1H, s), 7.93 (1H, bs), 7.86 (1H, d, J=8.0 Hz), 7.73 (2H, d, J=8.0 Hz), 7.59 (1H, d, J=8.1 Hz), 7.49 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.42 (1H, d, J=2.9 Hz), 7.26 (2H, d, J=7.8 Hz), 7.21 (1H, dd, J=2.9 Hz, J=9.3 Hz), 4.55-4.60 (1H, m), 4.46 (1H, t, J=5.7 Hz), 4.13 (2H, t, J=6.0 Hz), 3.87 (2H, s), 3.68 (2H, t, J=6.8 Hz), 2.57 (2H, t, J=6.8 Hz), 2.38 (3H, s), 1.80-1.96 (4H, m)

Mass spectrometric value (ESI-MS) 536, 537 (M−1)

Compound 1053 N-[2-(3,4-Dimethyl-benzylidene-hydrazinocarbonyl)-4-(4-fluoro-butoxy)-phenyl]-3-(2-hydroxy-ethylsulfanylmethyl)-benzamide

The title compound 1053 was produced in substantially the same manner as in Example S.

¹H-NMR (CD₃OD, 400 MHz): δ 8.45 (1H, d, J=9.3 Hz), 8.28 (1H, s), 7.93 (1H, s), 7.86 (1H, d, J=8.0 Hz), 7.65 (1H, s), 7.59 (1H, d, J=7.6 Hz), 7.53 (1H, d, J=8.8 Hz), 7.49 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.41 (1H, d, J=2.7 Hz), 7.17-7.24 (2H, m), 4.55-4.60 (1H, m), 4.46 (1H, t, J=5.7 Hz), 4.12 (2H, t, J=6.0 Hz), 3.87 (2H, s), 3.68 (2H, t, J=6.8 Hz), 2.57 (2H, t, J=6.8 Hz), 2.31 (3H, s), 2.30 (3H, s), 1.83-1.95 (4H, m)

Mass spectrometric value (ESI-MS) 550, 551 (M−1)

Compound 1054 N-[2-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-(4-fluoro-butoxy)-phenyl]-3-(2-hydroxy-ethylsulfanylmethyl)-benzamide

The title compound 1054 was produced in substantially the same manner as in Example S.

¹H-NMR (CD₃OD, 400 MHz): δ 8.42 (1H, d, J=9.2 Hz), 8.37 (1H, s), 8.32 (1H, s), 8.01-8.05 (1H, m), 7.92 (1H, s), 7.85 (1H, d, J=7.8 Hz), 7.67 (1H, d, J=8.3 Hz), 7.59 (1H, d, J=7.6 Hz), 7.49 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.42 (1H, d, J=2.7 Hz), 7.22 (1H, dd, J=2.7 Hz, J=9.2 Hz), 4.55-4.60 (1H, m), 4.46 (1H, t, J=5.7 Hz), 4.12 (2H, t, J=5.8 Hz), 3.86 (2H, s), 3.68 (2H, t, J=6.8 Hz), 2.57 (2H, t, J=7.0 Hz), 1.80-1.95 (4H, m)

Mass spectrometric value (ESI-MS) 624, 626, 627 (M−1)

Compound 1055 N-[4-(4-Fluoro-butoxy)-2-(4-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-3-(2-hydroxy-ethylsulfanylmethyl)-benzamide

The title compound 1055 was produced in substantially the same manner as in Example S.

¹H-NMR (CD₃OD, 400 MHz): δ 6.95-8.60 (12H, m), 4.55-4.62 (1H, m), 4.46 (1H, t, J=5.7 Hz), 4.12 (2H, t, J=6.0 Hz), 3.83-3.88 (3H, m), 3.79 (2H, s), 3.68 (2H, t, J=6.8 Hz), 2.57 (2H, t, J=6.8 Hz), 1.80-1.95 (4H, m)

Mass spectrometric value (ESI-MS) 552, 553 (M−1)

Compound 1056 3-{[Bis-(2-diethylamino-ethyl)-amino]-methyl}-N-[3-(4-methyl-benzylidene-hydrazinocarbonyl)-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl]-benzamide

The title compound 1056 was produced in substantially the same manner as in Example B.

¹H-NMR (CDCl₃, 400 MHz): δ 0.98 (12H, t, J=7.1 Hz), 1.92 (4H, m), 2.40 (3H, s), 2.45-2.65 (16H, m), 2.76 (2H, m), 2.89 (2H, m), 3.72 (2H, s), 7.24 (2H, m), 7.43 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.60 (1H, d, J=7.3 Hz), 7.69 (2H, d, J=8.0 Hz), 7.92 (1H, m), 8.00 (1H, s), 8.08 (1H, s)

Mass spectrometric value (ESI-MS) 644 (M−1)

Compound 1057 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[2-(3-fluoro-benzylidene-hydrazinocarbonyl)-4-(4-fluoro-butoxy)-phenyl]-benzamide

The title compound 1057 was produced in substantially the same manner as in Example S.

¹H-NMR (CD₃OD, 400 MHz): δ 8.41 (1H, d, J=9.0 Hz), 8.34 (1H, s), 7.88-7.98 (2H, m), 7.40-7.78 (6H, m), 7.14-7.26 (2H, m), 4.55-4.60 (1H, m), 4.46 (1H, t, J=5.7 Hz), 4.13 (2H, t, J=5.9 Hz), 3.68 (2H, s), 2.81 (2H, t, J=6.8 Hz), 2.68 (4H, q, J=7.1 Hz), 2.60 (2H, t, J=7.0 Hz), 2.29 (3H, s), 1.83-1.97 (4H, m), 1.06 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 592, 593, 594 (M−1) 638 (M+2×23)

Compound 1058 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[4-(4-fluoro-butoxy)-2-(4-methyl-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 1058 was produced in substantially the same manner as in Example S.

¹H-NMR (CD₃OD, 400 MHz): δ 8.42 (1H, d, J=9.0 Hz), 8.32 (1H, s), 7.95 (1H, s), 7.86-7.92 (1H, m), 7.71 (2H, d, J=8.1 Hz), 7.58 (1H, d, J=7.6 Hz), 7.51 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.41 (1H, d, J=2.7 Hz), 7.25 (2H, d, J=7.8 Hz), 7.19 (1H, dd, J=2.9 Hz, J=9.0 Hz), 4.55-4.60 (1H, m), 4.45 (1H, t, J=5.6 Hz), 4.11 (2H, t, J=5.7 Hz), 3.66 (2H, s), 2.72-2.79 (2H, m), 2.54-2.68 (6H, m), 2.37 (3H, s), 2.28 (3H, s), 1.80-1.95 (4H, m), 1.04 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 588, 589, 590 (M−1) 634, 635 (M+2×23)

Compound 1059 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-4-(4-fluoro-butoxy)-phenyl]-benzamide

The title compound 1059 was produced in substantially the same manner as in Example S.

¹H-NMR (CD₃OD, 400 MHz): δ 8.43 (1H, d, J=9.0 Hz), 8.28 (1H, s), 7.96 (1H, bs), 7.88-7.92 (1H, m), 7.63 (1H, s), 7.48-7.62 (3H, m), 7.40 (1H, d, J=2.7 Hz), 7.17-7.23 (2H, m), 4.55-4.60 (1H, m), 4.45 (1H, t, J=5.7 Hz), 4.12 (2H, t, J=5.9 Hz), 3.67 (2H, s), 2.72-2.80 (2H, m), 2.55-2.68 (6H, m), 2.30 (3H, s), 2.29 (3H, s), 2.28 (3H, s), 1.80-1.95 (4H, m), 1.03 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 602, 603 (M−1) 642, 648 (M+2×23)

Compound 1060 N-[2-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-(4-fluoro-butoxy)-phenyl]-3-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 1060 was produced in substantially the same manner as in Example S.

¹H-NMR (CD₃OD, 400 MHz): δ 8.36-8.42 (2H, m), 8.31 (1H, s), 7.98 -8.03 (1H, m), 7.95 (1H, s), 7.86-7.91 (1H, m), 7.67 (1H, d, J=8.3 Hz), 7.58 (1H, d, J=7.6 Hz), 7.51 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.42 (1H, d, J=2.9 Hz), 7.20 (1H, dd, J=2.9 Hz, J=9.0 Hz), 4.55-4.60 (1H, m), 4.45 (1H, t, J=5.7 Hz), 4.12 (2H, t, J=5.9 Hz), 3.66 (2H, s), 2.54-2.78 (8H, m), 2.27 (3H, s), 1.80-1.95 (4H, m), 1.03 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 676, 677, 679 (M−1)

Compound 1061 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[4-(4-fluoro-butoxy)-2-(4-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-benzamide

The title compound 1061 was produced in substantially the same manner as in Example S.

¹H-NMR (CD₃OD, 400 MHz): δ 8.43 (1H, d, J=9.3 Hz), 8.29 (1H, s), 7.95 (1H, bs), 7.87-7.92 (1H, m), 7.77 (2H, d, J=8.8 Hz), 7.56-7.61 (1H, m), 7.50 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.40 (1H, d, J=2.9 Hz), 7.19 (1H, dd, J=2.7 Hz, J=9.0 Hz), 6.97 (2H, d, J=8.8 Hz), 4.55-4.59 (1H, m), 4.45 (1H, t, J=5.7 Hz), 4.11 (2H, t, J=6.0 Hz), 3.83 (3H, s), 3.66 (2H, s), 2.54-2.77 (8H, m), 2.28 (3H, s), 1.80-1.97 (4H, m), 1.03 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 604, 605, 606 (M−1) 606 (M+1) 628, 629 (M+23)

Compound 1062 N-[2-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-(4-hydroxy-piperidin-1-yl)-phenyl]-3-(2-hydroxy-ethylsulfanylmethyl)-benzamide

The title compound 1062 was produced in substantially the same manner as in Example F.

¹H-NMR (CD₃OD, 400 MHz): δ 1.67 (2H, m), 2.00 (2H, m), 2.57 (2H, m), 2.99 (2H, m), 3.68 (4H, m), 3.80 (1H, m), 3.86 (2H, s), 7.25 (1H, m), 7.41 (1H, d, J=3.0 Hz), 7.49 (1H, m), 7.59 (1H, m), 7.69 (1H, d, J=8.6 Hz), 7.85 (1H, m), 7.92 (1H, m), 8.05 (1H, m), 8.34 (2H, m), 8.38 (1H, s)

Mass spectrometric value (ESI-MS) 633 (M−1)

Compound 1063 N-[2-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-(4-hydroxymethyl-piperidin-1-yl)-phenyl]-3-(2-hydroxy-ethylsulfanylmethyl)-benzamide

The title compound 1063 was produced in substantially the same manner as in Example F.

¹H-NMR (CD₃OD, 400 MHz): δ 1.39 (2H, m), 1.63 (1H, m), 1.88 (2H, m), 2.57 (2H, t, J=6.8 Hz), 2.76 (2H, m), 3.47 (2H, d, J=6.3 Hz), 3.68 (2H, t, J=6.8 Hz), 3.81 (2H, m), 3.86 (2H, s), 7.24 (1H, dd, J=9.2 Hz, J=2.8 Hz), 7.39 (1H, d, J=2.7 Hz), 7.49 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.58 (1H, d, J=7.6 Hz), 7.67 (1H, d, J=8.3 Hz), 7.84 (1H, d, J=7.6 Hz), 7.91 (1H, s), 8.03 (1H, m), 8.33 (2H, m), 8.37 (1H, s)

Mass spectrometric value (ESI-MS) 647 (M−1)

Compound 1064 N-[2-(3,4-Dimethyl-benzylidene-hydrazinocarbonyl)-4-morpholin-4-yl-phenyl]-3-(2-hydroxy-ethylsulfanylmethyl)-benzamide

The title compound 1064 was produced in substantially the same manner as in Example F.

¹H-NMR (CD₃OD, 400 MHz): δ 2.30 (3H, s), 2.31 (3H, s), 2.57 (2H, m), 3.24 (4H, m), 3.68 (2H, m), 3.87 (6H, m), 7.21 (2H, m), 7.38 (1H, s), 7.45-7.62 (3H, m), 7.66 (1H, m), 7.83-7.96 (2H, m), 8.28 (1H, s), 8.40 (1H, m)

Mass spectrometric value (ESI-MS) 545 (M−1)

Compound 1065 N-[2-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-morpholin-4-yl-phenyl]-3-(2-hydroxy-ethylsulfanylmethyl)-benzamide

The title compound 1065 was produced in substantially the same manner as in Example F.

¹H-NMR (DMSO-d₆, 400 MHz): δ 2.50 (2H, m), 3.20 (4H, m), 3.54 (2H, m), 3.78 (4H, m), 3.84 (2H, s), 7.24 (1H, d, J=8.1 Hz), 7.32 (1H, s), 7.53 (2H, m), 7.75-7.84 (2H, m), 7.87 (1H, s), 8.05 (1H, d, J=7.8 Hz), 8.20 (1H, s), 8.25 (1H, d, J=9.0 Hz), 8.48 (1H, s), 11.25 (1H, bs), 12.24 (1H, s)

Mass spectrometric value (ESI-MS) 619 (M−1)

Compound 1066 3-(2-Hydroxy-ethylsulfanylmethyl)-N-[2-(4-methoxy-benzylidene-hydrazinocarbonyl)-4-morpholin-4-yl-phenyl]-benzamide

The title compound 1066 was produced in substantially the same manner as in Example F.

¹H-NMR (CD₃OD, 400 MHz): δ 2.57 (2H, m), 3.30 (4H, m), 3.68 (2H, m), 3.86 (9H, m), 7.00 (2H, m), 7.24 (1H, m), 7.38 (1H, m), 7.49 (1H, m), 7.60 (1H, m), 7.75-7.95 (4H, m), 8.29 (1H, s), 8.42 (1H, m)

Mass spectrometric value (ESI-MS) 547 (M−1)

Compound 1067 N-[4-[1,4′]Bipiperazinyl-1′-yl-2-(4-chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-phenyl]-3-(2-hydroxy-ethylsulfanylmethyl)-benzamide

The title compound 1067 was produced in substantially the same manner as in Example F.

¹H-NMR (CD₃OD, 400 MHz): δ 1.60 (2H, m), 1.77 (6H, m), 2.11 (2H, m), 2.57 (2H, t, J=6.8 Hz), 2.75-3.02 (7H, m), 3.68 (2H, t, J=6.7 Hz), 3.86 (2H, s), 3.93 (2H, m), 7.26 (1H, m), 7.40 (1H, m), 7.49 (1H, m), 7.59 (1H, m), 7.68 (1H, d, J=8.1 Hz), 7.84 (1H, d, J=8.0 Hz), 7.92 (1H, s), 8.04 (1H, d, J=9.3 Hz), 8.30-8.40 (3H, m),

Mass spectrometric value (ESI-MS) 700 (M−1)

Compound 1068 N-[4-[1,4′]Bipiperazinyl-1′-yl-2-(4-methoxy-benzylidene-hydrazinocarbonyl)-phenyl]-3-(2-hydroxy-ethylsulfanyl-methyl)-benzamide

The title compound 1068 was produced in substantially the same manner as in Example F.

¹H-NMR (DMSO-d₆, 400 MHz): δ 1.39 (2H, m), 1.45-1.65 (6H, m), 1.84 (2H, m), 2.50 (7H, m), 2.70 (2H, m), 3.54 (2H, m), 3.83 (7H, m), 4.78 (1H, t, J=5.6 Hz), 7.02 (2H, d, J=8.8 Hz), 7.19 (1H, m), 7.31 (1H, m), 7.53 (2H, m), 7.70 (2H, d, J=7.8 Hz), 7.76 (1H, d, J=7.3 Hz), 7.86 (1H, s), 8.31 (1H, d, J=9.0 Hz), 8.39 (1H, s), 11.67 (1H, s), 11.88 (1H, s)

Mass spectrometric value (ESI-MS) 628 (M−1)

Compound 1069 N-[2-(3,4-Dimethyl-benzylidene-hydrazinocarbonyl)-4-(4-methyl-piperidin-1-yl)-phenyl]-3-(2-hydroxy-ethylsulfanylmethyl)-benzamide

The title compound 1069 was produced in substantially the same manner as in Example F.

¹H-NMR (DMSO-d₆, 400 MHz): δ 0.97 (3H, d, J=6.6 Hz), 1.27 (2H, m), 1.53 (1H, m), 1.74 (2H, m), 2.27 (3H, s), 2.28 (3H, s), 2.50 (2H, m), 2.70 (2H, m), 3.54 (2H, m), 3.75 (2H, m), 3.85 (2H, s), 4.77 (1H, t, J=5.7 Hz), 7.21 (2H, m), 7.31 (1H, m), 7.45 (1H, d, J=7.6 Hz), 7.52 (3H, m), 7.76 (1H, d, J=7.3 Hz), 7.87 (1H, s), 8.29 (1H, m), 8.37 (1H, s), 11.41 (1H, s), 11.90 (1H, s)

Mass spectrometric value (ESI-MS) 557 (M−1)

Compound 1070 N-[2-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-(4-methyl-piperidin-1-yl)-phenyl]-3-(2-hydroxy-ethylsulfanylmethyl)-benzamide

The title compound 1070 was produced in substantially the same manner as in Example F.

¹H-NMR (DMSO-d₆, 400 MHz): δ 0.96 (3H, d, J=6.3 Hz), 1.27 (2H, m), 1.53 (1H, m), 1.74 (2H, m), 2.50 (2H, m), 2.70 (2H, m), 3.54 (2H, m), 3.74 (2H, m), 3.84 (2H, s), 4.83 (1H, m), 7.19 (1H, d, J=8.6 Hz), 7.33 (1H, s), 7.52 (2H, m), 7.79 (2H, m), 7.86 (1H, s), 8.04 (1H, d, J=7.6 Hz), 8.23 (2H, m), 8.49 (1H, s), 12.24 (1H, s)

Mass spectrometric value (ESI-MS) 631 (M−1)

Compound 1071 3-(2-Hydroxy-ethylsulfanylmethyl)-N-[2-(4-methoxy-benzylidene-hydrazinocarbonyl)-4-(4-methyl-piperidin-1-yl)-phenyl]-benzamide

The title compound 1071 was produced in substantially the same manner as in Example F.

¹H-NMR (CD₃OD, 400 MHz): δ 1.01 (3H, d, J=6.1 Hz), 1.37 (2H, m), 1.55 (1H, m), 1.80 (2H, m), 2.57 (2H, t, J=6.7 Hz), 2.76 (2H, m), 3.68 (2H, m), 3.76 (2H, m), 3.84 (3H, s), 3.86 (2H, s), 6.99 (2H, d, J=8.8 Hz), 7.22 (1H, m), 7.38 (1H, m), 7.49 (1H, m), 7.58 (1H, m), 7.79 (2H, d, J=8.5 Hz), 7.85 (1H, d, J=7.6 Hz), 7.92 (1H, s), 8.30 (1H, s), 8.36 (1H, d, J=9.3 Hz)

Mass spectrometric value (ESI-MS) 559 (M−1)

Compound 1072 N-[2-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-(4-methyl-piperazin-1-yl)-phenyl]-3-(2-hydroxy-ethylsulfanylmethyl)-benzamide

The title compound 1072 was produced in substantially the same manner as in Example F.

¹H-NMR (CD₃OD, 400 MHz): δ 2.44 (3H, m), 2.56 (2H, m), 2.74 (4H, m), 3.30 (4H, m), 3.66 (2H, m), 3.85 (2H, m), 7.26 (1H, m), 7.40 (1H, s), 7.49 (1H, m), 7.58 (1H, m), 7.68 (1H, m), 7.83 (1H, m), 7.91 (1H, s), 8.02 (1H, m), 8.35 (3H, m)

Mass spectrometric value (ESI-MS) 632 (M−1)

Compound 1073 3-(2-Hydroxy-ethylsulfanylmethyl)-N-[2-(4-methoxy-benzylidene-hydrazinocarbonyl)-4-(4-methyl-piperazin-1-yl)-phenyl]-benzamide

The title compound 1073 was produced in substantially the same manner as in Example F.

¹H-NMR (CD₃OD, 400 MHz): δ 2.34 (3H, s), 2.57 (2H, t, J=6.8 Hz), 2.66 (4H, m), 3.31 (4H, m), 3.68 (2H, t, J=6.8 Hz), 3.84 (3H, s), 3.86 (2H, s), 6.99 (2H, d, J=8.8 Hz), 7.24 (1H, dd, J=9.1 Hz, J=2.7 Hz), 7.38 (1H, d, J=2.9 Hz), 7.49 (1H, d, J=7.7 Hz), 7.59 (1H, d, J=7.6 Hz), 7.79 (2H, d, J=8.8 Hz), 7.85 (1H, d, J=7.8 Hz), 7.92 (1H, s), 8.29 (1H, s), 8.40 (1H, d, J=9.0 Hz)

Mass spectrometric value (ESI-MS) 560 (M−1)

Compound 1074 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[2-(3,4-dimethyl-benzylidene-hydrazinocarbonyl)-4-morpholin-4-yl-phenyl]-benzamide

The title compound 1074 was produced in substantially the same manner as in Example F.

¹H-NMR (CDCl₃, 400 MHz): δ 1.04 (6H, t, J=7.1 Hz), 2.28 (9H, m), 2.59 (6H, m), 2.68 (2H, m), 2.85 (4H, m), 3.41 (4H, m), 3.64 (2H, s), 6.83 (1H, d, J=9.0 Hz), 6.97 (1H, s), 7.18 (1H, d, J=7.6 Hz), 7.47 (1H, dd, J=7.6 Hz, J=7.6 Hz), 7.56 (2H, m), 7.69 (1H, s), 7.89 (1H, d, J=7.6 Hz), 8.00 (1H, s), 8.09 (1H, d, J=9.0 Hz), 8.55 (1H, s), 11.22 (1H, s)

Mass spectrometric value (ESI-MS) 597 (M−1)

Compound 1075 N-[2-(4-Chloro-3-trifluoromethyl-benzylidene-hydrazinocarbonyl)-4-morpholin-4-yl-phenyl]-3-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-benzamide

The title compound 1075 was produced in substantially the same manner as in Example F.

¹H-NMR (CDCl₃, 400 MHz): δ 1.03 (6H, t, J=7.1 Hz), 2.28 (3H, s), 2.57 (6H, m), 2.66 (2H, m), 2.80 (4H, m), 3.34 (4H, m), 3.65 (2H, s), 6.80 (1H, d, J=8.6 Hz), 6.89 (1H, s), 7.50 (1H, m), 7.60 (2H, m), 7.89 (1H, d, J=7.6 Hz), 7.97 (1H, m), 8.03 (1H, s), 8.08 (1H, d, J=8.3 Hz), 8.13 (1H, s), 8.66 (1H, s), 11.08 (1H, s)

Mass spectrometric value (ESI-MS) 671 (M−1)

Compound 1076 3-{[(2-Diethylamino-ethyl)-methyl-amino]-methyl}-N-[2-(4-methoxy-benzylidene-hydrazinocarbonyl)-4-morpholin-4-yl-phenyl]-benzamide

The title compound 1076 was produced in substantially the same manner as in Example F.

¹H-NMR (CDCl₃, 400 MHz): δ 1.06 (6H, t, J=7.1 Hz), 2.25 (3H, s), 2.62 (6H, m), 2.72 (2H, m), 2.91 (4H, m), 3.46 (4H, m), 3.62 (2H, s), 3.82 (3H, s), 6.84-6.92 (3H, m), 7.07 (1H, s), 7.44 (1H, dd, J=7.7 Hz, J=7.7 Hz), 7.53 (1H, m), 7.75 (2H, d, J=8.5 Hz), 7.88 (1H, d, J=7.8 Hz), 7.97 (1H, s), 8.17 (1H, d, J=9.0 Hz), 8.57 (1H, s), 11.34 (1H, s)

Mass spectrometric value (ESI-MS) 599 (M−1)

Example U

Compound 1077 N-Benzoyloxy-5-chloro-2-(3-diethylaminomethyl-benzoylamino)-benzamide

2-Amino-5-chloro-benzoic acid methyl ester (1.5 g) was dissolved in anhydrous methylene chloride (25 ml). Pyridine (1.4 ml) and 3-(chloromethyl)benzoyl chloride (1.4 ml) were added dropwise to the solution at 0° C., and the mixture was then stirred at room temperature for 30 min. After the completion of the reaction, distilled water was added thereto at room temperature, and the mixture was subjected to separatory extraction with chloroform. The organic layer was then washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure to precipitate crystals. The precipitated crystals were collected by filtration through Kiriyama Rohto and were washed with ether to give 5-chloro-2-(3-chloromethyl-benzoylamino)-benzoic acid methyl ester as a useful intermediate (2.4 g, yield 90%).

5-Chloro-2-(3-chloromethyl-benzoylamino)-benzoic acid methyl ester (2.4 g) produced by the above process was dissolved in anhydrous methylene chloride (30 ml). Triethylamine (1.5 ml) and diethylamine (2.0 ml) were added dropwise to the solution at room temperature, and the mixture was then stirred at that temperature for 48 hr. After the completion of the reaction, the reaction system was concentrated under the reduced pressure, and the residue was purified by column chromatography eluted with a chloroform-methanol system to give 5-chloro-2-(3-diethylaminomethyl-benzoylamino)-benzoic acid methyl ester as a useful intermediate (1.9 g, yield 71%).

Subsequently, 5-chloro-2-(3-diethylaminomethyl-benzoylamino)-benzoic acid methyl ester (1.9 g) produced by the above process was dissolved in tetrahydrofuran/distilled water=4/1 (20 ml). Lithium hydroxide monohydrate (420 mg) was added to the solution at room temperature, and the mixture was then stirred at that temperature for 2.5 hr. After the completion of the reaction, the reaction system was concentrated under the reduced pressure, and the residue was purified by column chromatography eluted with a chloroform-methanol system to give 5-chloro-2-(3-diethylaminomethyl-benzoylamino)-benzoic acid (1.0 g, yield 56%).

5-Chloro-2-(3-diethylaminomethyl-benzoylamino)-benzoic acid (50 mg) produced by the above process was dissolved in N,N-dimethylformamide (1.0 ml). 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (38 mg), 1-hydroxy-benzotriazole monohydrate (28 mg), triethylamine (50 μl) and o-benzyl-hydroxylamine hydrochloride (40 mg) were added to the solution at room temperature, and the mixture was then stirred at that temperature for 24 hr. After the completion of the reaction, distilled water was added thereto at room temperature, and the mixture was subjected to separatory extraction with ethyl acetate. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a chloroform-methanol system to give the title compound 1077 (29 mg, yield 45%).

¹H-NMR (CD₃OD, 400 MHz): δ 8.55 (1H, d, J=9.0 Hz), 7.98 (1H, s), 7.87-7.91 (1H, m), 7.61-7.65 (2H, m), 7.40-7.56 (4H, m), 7.23-7.38 (3H, m), 4.99 (2H, s), 3.89 (2H, s), 2.73 (4H, q, J=7.2 Hz), 1.15 (6H, t, J=7.2 Hz)

Mass spectrometric value (ESI-MS) 463, 465, 466 (M−1) 465, 467 (M+1) 489 (M+23)

Starting compounds for compounds 1 to 1076 are shown in Table 1. In the table, compounds A, B, C, and B′ correspond to compounds described in Examples 1 to 11 and Examples A to T and schemes 1 and 2.

	TABLE 1
	A	B	C	B′
Compound 1	Methyl 2-aminobenzoate	3,4-Dimethoxybenzoyl	Trans-
		chloride	cinnamaldehyde
Compound 2	Methyl 2-aminobenzoate	3,4-Dimethoxybenzoyl	2-Fluorobenzaldehyde
		chloride
Compound 3	Methyl 2-aminobenzoate	3,4-Dimethoxybenzoyl	o-Tolualdehyde
		chloride
Compound 4	Methyl 2-aminobenzoate	3,4-Dimethoxybenzoyl	o-Methoxybenzaldehyde
		chloride
Compound 5	Methyl 2-aminobenzoate	3,4-Dimethoxybenzoyl	m-Methoxybenzaldehyde
		chloride
Compound 6	Methyl 2-aminobenzoate	3,4-Dimethoxybenzoyl	3,5-Ditert-butyl-
		chloride	4-hydroxybenzaldehyde
Compound 7	Methyl 2-aminobenzoate	3,4-Dimethoxybenzoyl	α-Methyl-
		chloride	cinnamaldehyde
Compound 8	Methyl 2-aminobenzoate	3,4-Dimethoxybenzoyl	3,5-Ditrifluoromethylbenzaldehyde
		chloride
Compound 9	Methyl 2-aminobenzoate	3,4-Dimethoxybenzoyl	3-Cyanobenzaldehyde
		chloride
Compound 10	Methyl 2-aminobenzoate	3,4-Dimethoxybenzoyl	2-Bromobenzaldehyde
		chloride
Compound 11	Methyl 2-aminobenzoate	3,4-Dimethoxybenzoyl	Vanillin
		chloride
Compound 12	Methyl 2-	3,4-Dimethoxybenzoyl	3,4,5-
	aminobenzoate	chloride	Trimethoxybenzaldehyde
Compound 13	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	Trans-
	bromobenzoate	chloride	cinnamaldehyde
Compound 14	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	2-Bromobenzaldehyde
	bromobenzoate	chloride
Compound 15	Methyl 2-aminobenzoate	3,4-Dimethoxybenzoyl	3-Fluorobenzaldehyde
		chloride
Compound 16	Methyl 2-aminobenzoate	3,4-Dimethoxybenzoyl	4-Fluorobenzaldehyde
		chloride
Compound 17	Methyl 2-aminobenzoate	3,4-Dimethoxybenzoyl	Benzaldehyde
		chloride
Compound 18	Methyl 2-aminobenzoate	3,4-Dimethoxybenzoyl	3-Hydroxybenzaldehyde
		chloride
Compound 19	Methyl 2-aminobenzoate	3,4-Dimethoxybenzoyl	4-Hydroxybenzaldehyde
		chloride
Compound 20	Methyl 2-aminobenzoate	3,4-Dimethoxybenzoyl	m-Tolualdehyde
		chloride
Compound 21	Methyl 2-aminobenzoate	3,4-Dimethoxybenzoyl	Furfural
		chloride
Compound 22	Methyl 2-aminobenzoate	3,4-Dimethoxybenzoyl	5-Methylfurfural
		chloride
Compound 23	Methyl 2-aminobenzoate	3,4-Dimethoxybenzoyl	2-Thiophene-
		chloride	carboxyaldehyde
Compound 24	Methyl 2-aminobenzoate	3,4-Dimethoxybenzoyl	3-Thiophene-
		chloride	carboxyaldehyde
Compound 25	Methyl 2-aminobenzoate	3,4-Dimethoxybenzoyl	2,4-Dihydroxybenzaldehyde
		chloride
Compound 26	Methyl 2-aminobenzoate	3,4-Dimethoxybenzoyl	3,4-Dihydroxybenzaldehyde
		chloride
Compound 27	Methyl 2-aminobenzoate	2-Fluorobenzoyl	Benzaldehyde
		chloride
Compound 28	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	2-Fluorobenzaldehyde
	bromobenzoate	chloride
Compound 29	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	3-Fluorobenzaldehyde
	bromobenzoate	chloride
Compound 30	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	o-Tolualdehyde
	bromobenzoate	chloride
Compound 31	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	m-Tolualdehyde
	bromobenzoate	chloride
Compound 32	Methyl 2-aminobenzoate	3,4-Dimethoxybenzoyl	3-Chloro-4-
		chloride	fluorobenzaldehyde
Compound 33	Methyl 2-aminobenzoate	3,4-Dimethoxybenzoyl	4-Trifluoromethoxybenzaldehyde
		chloride
Compound 34	Methyl 2-aminobenzoate	3,4-Dimethoxybenzoyl	3-Bromo-4-
		chloride	methoxybenzaldehyde
Compound 35	Methyl 2-aminobenzoate	3,4-Dimethoxybenzoyl	3-Chlorobenzaldehyde
		chloride
Compound 36	Methyl 2-aminobenzoate	3,4-Dimethoxybenzoyl	3,5-Dimethyl-4-
		chloride	hydroxybenzaldehyde
Compound 37	Methyl 2-aminobenzoate	3,4-Dimethoxybenzoyl	3-Ethoxy-4-
		chloride	hydroxybenzaldehyde
Compound 38	Methyl 2-aminobenzoate	2-Fluorobenzoyl	4-Fluorobenzaldehyde
		chloride
Compound 39	Methyl 2-aminobenzoate	2-Fluorobenzoyl	3-Hydroxybenzaldehyde
		chloride
Compound 40	Methyl 2-aminobenzoate	2-Fluorobenzoyl	p-Tolualdehyde
		chloride
Compound 41	Methyl 2-aminobenzoate	3,4-Dimethoxybenzoyl	4-Chloro-3-trifluoromethylbenzaldehyde
		chloride
Compound 42	Methyl 2-aminobenzoate	3,4-Dimethoxybenzoyl	4-Hydroxy-3-
		chloride	methylbenzaldehyde
Compound 43	Methyl 2-aminobenzoate	3,4-Dimethoxybenzoyl	2,5-Dimethylbenzaldehyde
		chloride
Compound 44	Methyl 2-aminobenzoate	3,4-Dimethoxybenzoyl	2-Fluoro-5-trifluoromethylbenzaldehyde
		chloride
Compound 45	Methyl 2-aminobenzoate	2-Fluorobenzoyl	4-Hydroxy-3-
		chloride	methylbenzaldehyde
Compound 46	Methyl 2-aminobenzoate	2-Fluorobenzoyl	2,5-Dimethylbenzaldehyde
		chloride
Compound 47	Methyl 2-aminobenzoate	4-Methoxybenzoyl	3-Fluorobenzaldehyde
		chloride
Compound 48	Methyl 2-aminobenzoate	4-Methoxybenzoyl	4-Fluorobenzaldehyde
		chloride
Compound 49	Methyl 2-aminobenzoate	4-Methoxybenzoyl	m-Tolualdehyde
		chloride
Compound 50	Methyl 2-aminobenzoate	4-Methoxybenzoyl	3-Hydroxybenzaldehyde
		chloride
Compound 51	Methyl 2-aminobenzoate	4-Methoxybenzoyl	p-Tolualdehyde
		chloride
Compound 52	Methyl 2-aminobenzoate	3,4-Dimethoxybenzoyl	4-Allyloxybenzaldehyde
		chloride
Compound 53	Methyl 2-aminobenzoate	3,4-Dimethoxybenzoyl	3,5-Dimethoxybenzaldehyde
		chloride
Compound 54	Methyl 2-aminobenzoate	3,4-Dimethoxybenzoyl	3-[3-(Trifluoromethyl)
		chloride	phenoxy]-
			benzaldehyde
Compound 55	Methyl 2-aminobenzoate	3,5-Dimethoxybenzoyl	3-Fluorobenzaldehyde
		chloride
Compound 56	Methyl 2-aminobenzoate	3,5-Dimethoxybenzoyl	4-Fluorobenzaldehyde
		chloride
Compound 57	Methyl 2-aminobenzoate	3,5-Dimethoxybenzoyl	p-Tolualdehyde
		chloride
Compound 58	Methyl 2-aminobenzoate	3,5-Dimethoxybenzoyl	3-Hydroxybenzaldehyde
		chloride
Compound 59	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	3-Chlorobenzaldehyde
	bromobenzoate	chloride
Compound 60	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	4-Chlorobenzaldehyde
	bromobenzoate	chloride
Compound 61	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	4-Fluorobenzaldehyde
	bromobenzoate	chloride
Compound 62	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	p-Tolualdehyde
	bromobenzoate	chloride
Compound 63	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	3-Hydroxybenzaldehyde
	bromobenzoate	chloride
Compound 64	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	4-Hydroxybenzaldehyde
	bromobenzoate	chloride
Compound 65	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	3-Fluorobenzaldehyde
	chlorobenzoate	chloride
Compound 66	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	4-Fluorobenzaldehyde
	chlorobenzoate	chloride
Compound 67	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	m-Tolualdehyde
	chlorobenzoate	chloride
Compound 68	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	p-Tolualdehyde
	chlorobenzoate	chloride
Compound 69	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	3-Hydroxybenzaldehyde
	chlorobenzoate	chloride
Compound 70	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	4-Hydroxybenzaldehyde
	chlorobenzoate	chloride
Compound 71	Methyl 2-amino-4-	3,4-Dimethoxybenzoyl	3-Fluorobenzaldehyde
	chlorobenzoate	chloride
Compound 72	Methyl 2-amino-4-	3,4-Dimethoxybenzoyl	4-Fluorobenzaldehyde
	chlorobenzoate	chloride
Compound 73	Methyl 2-amino-4-	3,4-Dimethoxybenzoyl	m-Tolualdehyde
	chlorobenzoate	chloride
Compound 74	Methyl 2-amino-4-	3,4-Dimethoxybenzoyl	p-Tolualdehyde
	chlorobenzoate	chloride
Compound 75	Methyl 2-amino-4-	3,4-Dimethoxybenzoyl	3-Hydroxybenzaldehyde
	chlorobenzoate	chloride
Compound 76	Methyl 2-aminobenzoate	4-Fluorobenzoyl	3-Fluorobenzaldehyde
		chloride
Compound 77	Methyl 2-aminobenzoate	4-Fluorobenzoyl	4-Fluorobenzaldehyde
		chloride
Compound 78	Methyl 2-aminobenzoate	4-Fluorobenzoyl	m-Tolualdehyde
		chloride
Compound 79	Methyl 2-	4-Fluorobenzoyl	p-Tolualdehyde
	aminobenzoate	chloride
Compound 80	Methyl 2-aminobenzoate	4-Fluorobenzoyl	3-Hydroxybenzaldehyde
		chloride
Compound 81	Methyl 2-aminobenzoate	3-Fluorobenzoyl	3-Fluorobenzaldehyde
		chloride
Compound 82	Methyl 2-aminobenzoate	3-Fluorobenzoyl	4-Fluorobenzaldehyde
		chloride
Compound 83	Methyl 2-aminobenzoate	3-Fluorobenzoyl	m-Tolualdehyde
		chloride
Compound 84	Methyl 2-aminobenzoate	3-Fluorobenzoyl	p-Tolualdehyde
		chloride
Compound 85	Methyl 2-aminobenzoate	3-Fluorobenzoyl	3-Hydroxybenzaldehyde
		chloride
Compound 86	Methyl 2-aminobenzoate	3-Fluorobenzoyl	4-Hydroxybenzaldehyde
		chloride
Compound 87	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	4-Chloro-3-trifluoromethylbenzaldehyde
	bromobenzoate	chloride
Compound 88	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	4-Chloro-3-trifluoromethylbenzaldehyde
	chlorobenzoate	chloride
Compound 89	Methyl 2-aminobenzoate	3,5-Dimethoxybenzoyl	4-Chloro-3-trifluoromethylbenzaldehyde
		chloride
Compound 90	Methyl 2-aminobenzoate	4-Methoxybenzoyl	4-Chloro-3-trifluoromethylbenzaldehyde
		chloride
Compound 91	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	3,4-Dimethylbenzaldehyde
	bromobenzoate	chloride
Compound 92	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	3,4-Dimethylbenzaldehyde
	chlorobenzoate	chloride
Compound 93	Methyl 2-	3,5-Dimethoxybenzoyl	3,4-Dimethylbenzaldehyde
	aminobenzoate	chloride
Compound 94	Methyl 2-	4-Methoxybenzoyl	3,4-Dimethylbenzaldehyde
	aminobenzoate	chloride
Compound 95	Methyl 2-	3-Fluorobenzoyl	3,4-Dimethylbenzaldehyde
	aminobenzoate	chloride
Compound 96	Methyl 2-	4-Fluorobenzoyl	3,4-Dimethylbenzaldehyde
	aminobenzoate	chloride
Compound 97	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	3-Bromo-4-
	bromobenzoate	chloride	methoxybenzaldehyde
Compound 98	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	3-Bromo-4-
	chlorobenzoate	chloride	methoxybenzaldehyde
Compound 99	Methyl 2-aminobenzoate	3,5-Dimethoxybenzoyl	3-Bromo-4-
		chloride	methoxybenzaldehyde
Compound 100	Methyl 2-aminobenzoate	4-Methoxybenzoyl	3-Bromo-4-
		chloride	methoxybenzaldehyde
Compound 101	Methyl 2-aminobenzoate	3-Fluorobenzoyl	3-Bromo-4-
		chloride	methoxybenzaldehyde
Compound 102	Methyl 2-aminobenzoate	4-Fluorobenzoyl	3-Bromo-4-
		chloride	methoxybenzaldehyde
Compound 103	Methyl 2-aminobenzoate	3,4-Dimethoxybenzoyl	3-Nitrobenzaldehyde
		chloride
Compound 104	Methyl 2-aminobenzoate	3,4-Dimethoxybenzoyl	4-Dimethylaminobenzaldehyde
		chloride
Compound 105	Methyl 2-amino-5-	4-Fluorobenzoyl	3-Fluorobenzaldehyde
	bromobenzoate	chloride
Compound 106	Methyl 2-amino-5-	4-Fluorobenzoyl	4-Fluorobenzaldehyde
	bromobenzoate	chloride
Compound 107	Methyl 2-amino-5-	4-Fluorobenzoyl	3-Chlorobenzaldehyde
	bromobenzoate	chloride
Compound 108	Methyl 2-amino-5-	4-Fluorobenzoyl	4-Chlorobenzaldehyde
	bromobenzoate	chloride
Compound 109	Methyl 2-amino-5-	4-Fluorobenzoyl	3-Hydroxybenzaldehyde
	bromobenzoate	chloride
Compound 110	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	3-Pyridine-
	bromobenzoate	chloride	carboxyaldehyde
Compound 111	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	3-Pyridine-
	chlorobenzoate	chloride	carboxyaldehyde
Compound 112	Methyl 2-aminobenzoate	4-Methoxybenzoyl	3-Pyridine-
		chloride	carboxyaldehyde
Compound 113	Methyl 2-aminobenzoate	4-Fluorobenzoyl	3-Pyridine-
		chloride	carboxyaldehyde
Compound 114	Methyl 2-amino-5-	3,5-Dimethoxybenzoyl	3-Fluorobenzaldehyde
	bromobenzoate	chloride
Compound 115	Methyl 2-amino-5-	3,5-Dimethoxybenzoyl	4-Fluorobenzaldehyde
	bromobenzoate	chloride
Compound 116	Methyl 2-amino-5-	3,5-Dimethoxybenzoyl	3-Chlorobenzaldehyde
	bromobenzoate	chloride
Compound 117	Methyl 2-amino-5-	3,5-Dimethoxybenzoyl	4-Chlorobenzaldehyde
	bromobenzoate	chloride
Compound 118	Methyl 2-amino-5-	3,5-Dimethoxybenzoyl	m-Tolualdehyde
	bromobenzoate	chloride
Compound 119	Methyl 2-amino-5-	3,5-Dimethoxybenzoyl	p-Tolualdehyde
	bromobenzoate	chloride
Compound 120	Methyl 2-aminobenzoate	3-Trifluoromethoxybenzoyl	3-Fluorobenzaldehyde
		chloride
Compound 121	Methyl 2-aminobenzoate	3-Trifluoromethoxybenzoyl	4-Fluorobenzaldehyde
		chloride
Compound 122	Methyl 2-aminobenzoate	3-Trifluoromethoxybenzoyl	3-Chlorobenzaldehyde
		chloride
Compound 123	Methyl 2-aminobenzoate	3-Trifluoromethoxybenzoyl	4-Chlorobenzaldehyde
		chloride
Compound 124	Methyl 2-aminobenzoate	3-Trifluoromethoxybenzoyl	p-Tolualdehyde
		chloride
Compound 125	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	4-Fluorobenzaldehyde
	hydroxy-benzoate	chloride
Compound 126	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	3,4-Dimethoxybenzaldehyde
	chlorobenzoate	chloride
Compound 127	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	3,4-Dimethoxybenzaldehyde
	bromobenzoate	chloride
Compound 128	Methyl 2-amino-5-	3,5-Dimethoxybenzoyl	3,4-Dimethoxybenzaldehyde
	bromobenzoate	chloride
Compound 129	Methyl 2-aminobenzoate	Nicotinoyl chloride	3-Fluorobenzaldehyde
		hydrochloride
Compound 130	Methyl 2-aminobenzoate	Nicotinoyl chloride	4-Fluorobenzaldehyde
		hydrochloride
Compound 131	Methyl 2-aminobenzoate	Nicotinoyl chloride	m-Tolualdehyde
		hydrochloride
Compound 132	Methyl 2-aminobenzoate	Nicotinoyl chloride	p-Tolualdehyde
		hydrochloride
Compound 133	Methyl 2-aminobenzoate	Nicotinoyl chloride	3,4-Dimethylbenzaldehyde
		hydrochloride
Compound 134	Methyl 2-aminobenzoate	Isonicotinoyl	3-Fluorobenzaldehyde
		chloride
		hydrochloride
Compound 135	Methyl 2-aminobenzoate	Isonicotinoyl	4-Fluorobenzaldehyde
		chloride
		hydrochloride
Compound 136	Methyl 2-aminobenzoate	Isonicotinoyl	m-Tolualdehyde
		chloride
		hydrochloride
Compound 137	Methyl 2-aminobenzoate	Isonicotinoyl	p-Tolualdehyde
		chloride
		hydrochloride
Compound 138	Methyl 2-aminobenzoate	Isonicotinoyl	3,4-Dimethylbenzaldehyde
		chloride
		hydrochloride
Compound 139	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	4-Fluorobenzaldehyde
	hydroxybenzoate	chloride
Compound 140	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	4-Fluorobenzaldehyde
	hydroxybenzoate	chloride
Compound 141	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	3-Fluorobenzaldehyde
	methoxybenzoate	chloride
Compound 142	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	4-Fluorobenzaldehyde
	methoxybenzoate	chloride
Compound 143	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	m-Tolualdehyde
	methoxybenzoate	chloride
Compound 144	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	p-Tolualdehyde
	methoxybenzoate	chloride
Compound 145	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	3,4-Dimethylbenzaldehyde
	methoxybenzoate	chloride
Compound 146	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	3-Fluorobenzaldehyde
	methylbenzoate	chloride
Compound 147	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	4-Fluorobenzaldehyde
	methylbenzoate	chloride
Compound 148	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	m-Tolualdehyde
	methylbenzoate	chloride
Compound 149	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	p-Tolualdehyde
	methylbenzoate	chloride
Compound 150	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	3,4-Dimethylbenzaldehyde
	methylbenzoate	chloride
Compound 151	Methyl 2-amino-5-	2-Furoyl chloride	3-Fluorobenzaldehyde
	bromobenzoate
Compound 152	Methyl 2-amino-5-	2-Furoyl chloride	4-Fluorobenzaldehyde
	bromobenzoate
Compound 153	Methyl 2-amino-5-	2-Furoyl chloride	m-Tolualdehyde
	bromobenzoate
Compound 154	Methyl 2-amino-5-	2-Furoyl chloride	p-Tolualdehyde
	bromobenzoate
Compound 155	Methyl 2-amino-5-	2-Furoyl chloride	3,4-Dimethylbenzaldehyde
	bromobenzoate
Compound 156	Methyl 2-amino-5-	2-Furoyl chloride	4-Chloro-3-trifluoromethylbenzaldehyde
	bromobenzoate
Compound 157	Methyl 2-amino-5-	Thiophene-2-	3-Fluorobenzaldehyde
	bromobenzoate	carbonyl chloride
Compound 158	Methyl 2-amino-5-	Thiophene-2-	4-Fluorobenzaldehyde
	bromobenzoate	carbonyl chloride
Compound 159	Methyl 2-amino-5-	Thiophene-2-	m-Tolualdehyde
	bromobenzoate	carbonyl chloride
Compound 160	Methyl 2-amino-5-	Thiophene-2-	p-Tolualdehyde
	bromobenzoate	carbonyl chloride
Compound 161	Methyl 2-amino-5-	Thiophene-2-	3,4-Dimethylbenzaldehyde
	bromobenzoate	carbonyl chloride
Compound 162	Methyl 2-amino-5-	Thiophene-2-	4-Chloro-3-trifluoromethylbenzaldehyde
	bromobenzoate	carbonyl chloride
Compound 163	Methyl 2-aminobenzoate	Isonicotinoyl	3,4-Dimethylbenzaldehyde
		chloride
		hydrochloride
Compound 164	Methyl 2-	Nicotinoyl chloride	p-Tolualdehyde
	aminobenzoate	hydrochloride
Compound 165	Methyl 2-	Nicotinoyl chloride	3,4-Dimethylbenzaldehyde
	aminobenzoate	hydrochloride
Compound 166	Methyl 2-amino-5-	Isonicotinoyl	3-Fluorobenzaldehyde
	bromobenzoate	chloride
		hydrochloride
Compound 167	Methyl 2-amino-5-	Isonicotinoyl	4-Fluorobenzaldehyde
	bromobenzoate	chloride
		hydrochloride
Compound 168	Methyl 2-amino-5-	Isonicotinoyl	m-Tolualdehyde
	bromobenzoate	chloride
		hydrochloride
Compound 169	Methyl 2-amino-5-	Isonicotinoyl	p-Tolualdehyde
	bromobenzoate	chloride
		hydrochloride
Compound 170	Methyl 2-amino-5-	Isonicotinoyl	3,4-Dimethylbenzaldehyde
	bromobenzoate	chloride
		hydrochloride
Compound 171	Methyl 2-amino-5-	Isonicotinoyl	4-Chloro-3-trifluoromethylbenzaldehyde
	bromobenzoate	chloride
		hydrochloride
Compound 172	Methyl 2-amino-5-	Nicotinoyl chloride	3-Fluorobenzaldehyde
	bromobenzoate	hydrochloride
Compound 173	Methyl 2-amino-5-	Nicotinoyl chloride	4-Fluorobenzaldehyde
	bromobenzoate	hydrochloride
Compound 174	Methyl 2-amino-5-	Nicotinoyl chloride	m-Tolualdehyde
	bromobenzoate	hydrochloride
Compound 175	Methyl 2-amino-5-	Nicotinoyl chloride	p-Tolualdehyde
	bromobenzoate	hydrochloride
Compound 176	Methyl 2-amino-5-	Nicotinoyl chloride	3,4-Dimethylbenzaldehyde
	bromobenzoate	hydrochloride
Compound 177	Methyl 2-amino-5-	Nicotinoyl chloride	4-Chloro-3-trifluoromethylbenzaldehyde
	bromobenzoate	hydrochloride
Compound 178	Methyl 2-amino-5-	4-Ethyl benzoyl	3-Fluorobenzaldehyde
	bromobenzoate	chloride
Compound 179	Methyl 2-amino-5-	4-Ethyl benzoyl	4-Fluorobenzaldehyde
	bromobenzoate	chloride
Compound 180	Methyl 2-amino-5-	4-Ethyl benzoyl	m-Tolualdehyde
	bromobenzoate	chloride
Compound 181	Methyl 2-amino-5-	4-Ethyl benzoyl	p-Tolualdehyde
	bromobenzoate	chloride
Compound 182	Methyl 2-amino-5-	4-Ethyl benzoyl	3,4-Dimethylbenzaldehyde
	bromobenzoate	chloride
Compound 183	Methyl 2-amino-5-	4-Ethyl benzoyl	4-Chloro-3-trifluoromethylbenzaldehyde
	bromobenzoate	chloride
Compound 184	Methyl 2-amino-5-	Nicotinoyl chloride	3-Fluorobenzaldehyde
	chlorobenzoate	hydrochloride
Compound 185	Methyl 2-amino-5-	Nicotinoyl chloride	4-Fluorobenzaldehyde
	chlorobenzoate	hydrochloride
Compound 186	Methyl 2-amino-5-	Nicotinoyl chloride	m-Tolualdehyde
	chlorobenzoate	hydrochloride
Compound 187	Methyl 2-amino-5-	Nicotinoyl chloride	p-Tolualdehyde
	chlorobenzoate	hydrochloride
Compound 188	Methyl 2-amino-5-	Nicotinoyl chloride	3,4-Dimethylbenzaldehyde
	chlorobenzoate	hydrochloride
Compound 189	Methyl 2-amino-5-	Nicotinoyl chloride	4-Chloro-3-trifluoromethylbenzaldehyde
	chlorobenzoate	hydrochloride
Compound 190	Methyl 2-amino-5-	Isonicotinoyl	4-Fluorobenzaldehyde
	chlorobenzoate	chloride
		hydrochloride
Compound 191	Methyl 2-amino-5-	Isonicotinoyl	m-Tolualdehyde
	chlorobenzoate	chloride
		hydrochloride
Compound 192	Methyl 2-amino-5-	Isonicotinoyl	p-Tolualdehyde
	chlorobenzoate	chloride
		hydrochloride
Compound 193	Methyl 2-amino-5-	Isonicotinoyl	3,4-Dimethylbenzaldehyde
	chlorobenzoate	chloride
		hydrochloride
Compound 194	Methyl 2-amino-5-	Isonicotinoyl	4-Chloro-3-trifluoromethylbenzaldehyde
	chlorobenzoate	chloride
		hydrochloride
Compound 195	Methyl 2-amino-5-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	4-Mercapto-
	bromobenzoate	benzoyl chloride		pyridine
Compound 196	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	4-Mercapto-
	bromobenzoate	benzoyl chloride		pyridine
Compound 197	Methyl 2-amino-5-	3-(Chloromethyl)-	m-Tolualdehyde	4-Mercapto-
	bromobenzoate	benzoyl chloride		pyridine
Compound 198	Methyl 2-amino-5-	3-(Chloromethyl)-	p-Tolualdehyde	4-Mercapto-
	bromobenzoate	benzoyl chloride		pyridine
Compound 199	Methyl 2-amino-5-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	4-Mercapto-
	bromobenzoate	benzoyl chloride		pyridine
Compound 200	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Chloro-3-	4-Mercapto-
	bromobenzoate	benzoyl chloride	trifluoromethylbenzaldehyde	pyridine
Compound 201	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	1-Methylpyrrole-
	bromobenzoate	chloride	2-carboxaldehyde
Compound 202	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	4,5-Dimethyl-2-
	bromobenzoate	chloride	furancarboxaldehyde
Compound 203	Methyl 2-aminobenzoate	Isonicotinoyl	p-Tolualdehyde
		chloride
		hydrochloride
Compound 204	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	3-Fluorobenzaldehyde
	iodobenzoate	chloride
Compound 205	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	4-Fluorobenzaldehyde
	iodobenzoate	chloride
Compound 206	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	m-Tolualdehyde
	iodobenzoate	chloride
Compound 207	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	p-Tolualdehyde
	iodobenzoate	chloride
Compound 208	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	3,4-Dimethylbenzaldehyde
	iodobenzoate	chloride
Compound 209	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	4-Chloro-3-
	iodobenzoate	chloride	trifluoromethylbenzaldehyde
Compound 210	Methyl 2-aminobenzoate	Isonicotinoyl	1-Methylpyrrole-
		chloride	2-carboxaldehyde
		hydrochloride
Compound 211	Methyl 2-amino-5-	Nicotinoyl chloride	1-Methylpyrrole-
	bromobenzoate	hydrochloride	2-carboxaldehyde
Compound 212	Methyl 2-amino-5-	Nicotinoyl chloride	1-Methylpyrrole-
	chlorobenzoate	hydrochloride	2-carboxaldehyde
Compound 213	Methyl 2-	3,4-Dimethoxybenzoyl	3-Fluoro-
	aminobenzoate	chloride	acetophenone
Compound 214	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	3-Fluoro-
	bromobenzoate	chloride	acetophenone
Compound 215	Methyl 2-amino-5-	Nicotinoyl chloride	3-Methyl-
	bromobenzoate	hydrochloride	acetophenone
Compound 216	Methyl 2-amino-5-	Nicotinoyl chloride	4-Methyl-
	bromobenzoate	hydrochloride	acetophenone
Compound 217	Methyl 2-amino-5-	Nicotinoyl chloride	4-Methyl-
	chlorobenzoate	hydrochloride	acetophenone
Compound 218	Methyl 2-	Nicotinoyl chloride	4,5-Dimethyl-2-
	aminobenzoate	hydrochloride	furancarboxaldehyde
Compound 219	Methyl 2-	Isonicotinoyl	4,5-Dimethyl-2-
	aminobenzoate	chloride	furancarboxaldehyde
		hydrochloride
Compound 220	Methyl 2-amino-5-	Nicotinoyl chloride	4,5-Dimethyl-2-
	bromobenzoate	hydrochloride	furancarboxaldehyde
Compound 221	Methyl 2-amino-5-	Isonicotinoyl	4,5-Dimethyl-2-
	bromobenzoate	chloride	furancarboxaldehyde
		hydrochloride
Compound 222	Methyl 2-amino-5-	Nicotinoyl chloride	4,5-Dimethyl-2-
	chlorobenzoate	hydrochloride	furancarboxaldehyde
Compound 223	Methyl 2-amino-5-	Isonicotinoyl	4,5-Dimethyl-2-
	chlorobenzoate	chloride	furancarboxaldehyde
		hydrochloride
Compound 224	Methyl 2-	Benzoyl chloride	Benzaldehyde
	aminobenzoate
Compound 225	Methyl 2-aminobenzoate	Benzoyl chloride	2-Fluorobenzaldehyde
Compound 226	Methyl 2-aminobenzoate	Benzoyl chloride	3-Fluorobenzaldehyde
Compound 227	Methyl 2-amino-3,4-	3,4-Dimethoxybenzoyl	Benzaldehyde
	dimethoxybenzoate	chloride
Compound 228	Methyl 2-	Benzoyl chloride	2-Bromobenzaldehyde
	aminobenzoate
Compound 229	Methyl 2-	Benzoyl chloride	o-Tolualdehyde
	aminobenzoate
Compound 230	Methyl 2-amino-3,4-	3,4-Dimethoxybenzoyl	o-Tolualdehyde
	dimethoxybenzoate	chloride
Compound 231	Methyl 2-aminobenzoate	3,4-Dimethoxybenzoyl	2-Chlorobenzaldehyde
		chloride
Compound 232	Methyl 2-	3,4-Dimethoxybenzoyl	6-Methoxy-2-
	aminobenzoate	chloride	naphthaldehyde
Compound 233	Methyl 2-aminobenzoate	3,4-Dimethoxybenzoyl	4-Biphenyl-
		chloride	carboxaldehyde
Compound 234	Methyl 2-	3,4-Dimethoxybenzoyl	4-Bromobenzaldehyde
	aminobenzoate	chloride
Compound 235	Methyl 2-aminobenzoate	Benzoyl chloride	Trans-
			cinnamaldehyde
Compound 236	Methyl 2-	2-Fluorobenzoyl	2-Fluorobenzaldehyde
	aminobenzoate	chloride
Compound 237	Methyl 2-	2-Fluorobenzoyl	3-Fluorobenzaldehyde
	aminobenzoate	chloride
Compound 238	Methyl 2-	2-Fluorobenzoyl	m-Tolualdehyde
	aminobenzoate	chloride
Compound 239	Methyl 2-aminobenzoate	2-Fluorobenzoyl	2-Hydroxy-3-tert-
		chloride	butylbenzaldehyde
Compound 240	Methyl 2-	3,4-Dimethoxybenzoyl	4-Nitrobenzaldehyde
	aminobenzoate	chloride
Compound 241	Methyl 2-aminobenzoate	3,4-Dimethoxybenzoyl	4-Diethylaminobenzaldehyde
		chloride
Compound 242	Methyl 2-amino-5-	3,5-Dimethoxybenzoyl	3-Fluorobenzaldehyde
	hydroxybenzoate	chloride
Compound 243	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	2-Pyridyl-
	bromobenzoate	chloride	carboxaldehyde
Compound 244	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	2-Pyridyl-
	chlorobenzoate	chloride	carboxaldehyde
Compound 245	Methyl 2-aminobenzoate	3,4-Dimethoxybenzoyl	2-Pyridyl-
		chloride	carboxaldehyde
Compound 246	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	6-Methyl-2-
	chlorobenzoate	chloride	pyridine-
			carboxaldehyde
Compound 247	Methyl 2-	3,4-Dimethoxybenzoyl	6-Methyl-2-
	aminobenzoate	chloride	pyridine-
			carboxaldehyde
Compound 248	Methyl 2-amino-5-	4-tert-butylbenzoyl	m-Tolualdehyde
	bromobenzoate	chloride
Compound 249	Methyl 2-	Isonicotinoyl	3-Methylacetophenone
	aminobenzoate	chloride
		hydrochloride
Compound 250	Methyl 2-amino-5-	Nicotinoyl chloride	3-Methylacetophenone
	chlorobenzoate	hydrochloride
Compound 251	Methyl 2-	Nicotinoyl chloride	4-Methylacetophenone
	aminobenzoate	hydrochloride
Compound 252	Methyl 2-amino-5-	Nicotinoyl chloride	p-Tolualdehyde
	bromobenzoate	hydrochloride
Compound 253	Methyl 2-	Isonicotinoyl	m-Tolualdehyde
	aminobenzoate	chloride
		hydrochloride
Vacant number
Compound 255	Methyl 2-amino-5-	4-(Chloromethyl)-	3-Fluorobenzaldehyde	4-Mercapto-
	bromobenzoate	benzoyl chloride		pyridine
Compound 256	Methyl 2-amino-5-	4-(Chloromethyl)-	4-Fluorobenzaldehyde	4-Mercapto-
	bromobenzoate	benzoyl chloride		pyridine
Compound 257	Methyl 2-amino-5-	4-(Chloromethyl)-	m-Tolualdehyde	4-Mercapto-
	bromobenzoate	benzoyl chloride		pyridine
Compound 258	Methyl 2-amino-5-	4-(Chloromethyl)-	p-Tolualdehyde	4-Mercapto-
	bromobenzoate	benzoyl chloride		pyridine
Compound 259	Methyl 2-amino-5-	4-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	4-Mercapto-
	bromobenzoate	benzoyl chloride		pyridine
Compound 260	Methyl 2-amino-5-	4-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	4-Mercapto-
	bromobenzoate	benzoyl chloride		pyridine
Compound 261	Methyl 2-amino-5-	4-(Chloromethyl)-	3-Fluorobenzaldehyde	2-Mercapto-
	bromobenzoate	benzoyl chloride		ethanol
Compound 262	Methyl 2-amino-5-	4-(Chloromethyl)-	4-Fluorobenzaldehyde	2-Mercapto-
	bromobenzoate	benzoyl chloride		ethanol
Compound 263	Methyl 2-amino-5-	4-(Chloromethyl)-	m-Tolualdehyde	2-Mercapto-
	bromobenzoate	benzoyl chloride		ethanol
Compound 264	Methyl 2-amino-5-	4-(Chloromethyl)-	p-Tolualdehyde	2-Mercapto-
	bromobenzoate	benzoyl chloride		ethanol
Compound 265	Methyl 2-amino-5-	4-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	2-Mercapto-
	bromobenzoate	benzoyl chloride		ethanol
Compound 266	Methyl 2-amino-5-	4-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	2-Mercapto-
	bromobenzoate	benzoyl chloride		ethanol
Compound 267	Methyl 2-amino-5-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	3-Mercapto-
	bromobenzoate	benzoyl chloride		1,2,4-triazole
Compound 268	Methyl 2-amino-5-	3-(Chloromethyl)-	p-Tolualdehyde	3-Mercapto-
	bromobenzoate	benzoyl chloride		1,2,4-triazole
Compound 269	Methyl 2-amino-5-	3-(Chloromethyl)-	m-Tolualdehyde	3-Mercapto-
	bromobenzoate	benzoyl chloride		1,2,4-triazole
Compound 270	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	3-Mercapto-
	bromobenzoate	benzoyl chloride		1,2,4-triazole
Compound 271	Methyl 2-amino-5-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	3-Mercapto-
	bromobenzoate	benzoyl chloride		1,2,4-triazole
Compound 272	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	3-Mercapto-
	bromobenzoate	benzoyl chloride		1,2,4-triazole
Compound 273	Methyl 2-amino-5-	4-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	3-Mercapto-1-
	bromobenzoate	benzoyl chloride		propanol
Compound 274	Methyl 2-amino-5-	4-(Chloromethyl)-	p-Tolualdehyde	3-Mercapto-1-
	bromobenzoate	benzoyl chloride		propanol
Compound 275	Methyl 2-amino-5-	4-(Chloromethyl)-	m-Tolualdehyde	3-Mercapto-1-
	bromobenzoate	benzoyl chloride		propanol
Compound 276	Methyl 2-amino-5-	4-(Chloromethyl)-	4-Fluorobenzaldehyde	3-Mercapto-1-
	bromobenzoate	benzoyl chloride		propanol
Compound 277	Methyl 2-amino-5-	4-(Chloromethyl)-	3-Fluorobenzaldehyde	3-Mercapto-1-
	bromobenzoate	benzoyl chloride		propanol
Compound 278	Methyl 2-amino-5-	4-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	3-Mercapto-1-
	bromobenzoate	benzoyl chloride		propanol
Compound 279	Methyl 2-amino-5-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	4-(2-Aminoethyl)-
	bromobenzoate	benzoyl chloride		morpholine
Compound 280	Methyl 2-amino-5-	4-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	N,N-Diethyl-
	bromobenzoate	benzoyl chloride		N′-methyl-
				ethylenediamine
Compound 281	Methyl 2-amino-5-	4-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	4-(2-Aminoethyl)-
	bromobenzoate	benzoyl chloride		morpholine
Compound 282	Methyl 2-amino-5-	4-(Chloromethyl)-	p-Tolualdehyde	4-(2-Aminoethyl)-
	bromobenzoate	benzoyl chloride		morpholine
Compound 283	Methyl 2-amino-5-	4-(Chloromethyl)-	m-Tolualdehyde	4-(2-Aminoethyl)-
	bromobenzoate	benzoyl chloride		morpholine
Compound 284	Methyl 2-amino-5-	4-(Chloromethyl)-	4-Fluorobenzaldehyde	4-(2-Aminoethyl)-
	bromobenzoate	benzoyl chloride		morpholine
Compound 285	Methyl 2-amino-5-	4-(Chloromethyl)-	p-Tolualdehyde	N,N-Diethyl-
	bromobenzoate	benzoyl chloride		N′-methyl-
				ethylenediamine
Compound 286	Methyl 2-amino-5-	4-(Chloromethyl)-	m-Tolualdehyde	N,N-Diethyl-
	bromobenzoate	benzoyl chloride		N′-methyl-
				ethylenediamine
Compound 287	Methyl 2-amino-5-	4-(Chloromethyl)-	4-Fluorobenzaldehyde	N,N-Diethyl-
	bromobenzoate	benzoyl chloride		N′-methyl-
				ethylenediamine
Compound 288	Methyl 2-amino-5-	4-(Chloromethyl)-	3-Fluorobenzaldehyde	N,N-Diethyl-
	bromobenzoate	benzoyl chloride		N′-methyl-
				ethylenediamine
Compound 289	Methyl 2-amino-5-	4-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	N,N-Diethyl-
	bromobenzoate	benzoyl chloride		N′-methyl-
				ethylenediamine
Compound 290	Methyl 2-amino-5-	4-(Chloromethyl)-	p-Methoxybenzaldehyde	N,N-Diethyl-
	bromobenzoate	benzoyl chloride		N′-methyl-
				ethylenediamine
Compound 291	Methyl 2-amino-5-	4-(Chloromethyl)-	m-Methoxybenzaldehyde	N,N-Diethyl-
	bromobenzoate	benzoyl chloride		N′-methyl-
				ethylenediamine
Compound 292	Methyl 2-amino-5-	4-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	N,N-Diethyl-
	bromobenzoate	benzoyl chloride		ethylenediamine
Compound 293	Methyl 2-amino-5-	4-(Chloromethyl)-	p-Tolualdehyde	N,N-Diethyl-
	bromobenzoate	benzoyl chloride		ethylenediamine
Compound 294	Methyl 2-amino-5-	4-(Chloromethyl)-	m-Tolualdehyde	N,N-Diethyl-
	bromobenzoate	benzoyl chloride		ethylenediamine
Compound 295	Methyl 2-amino-5-	4-(Chloromethyl)-	4-Fluorobenzaldehyde	N,N-Diethyl-
	bromobenzoate	benzoyl chloride		ethylenediamine
Compound 296	Methyl 2-amino-5-	4-(Chloromethyl)-	3-Fluorobenzaldehyde	N,N-Diethyl-
	bromobenzoate	benzoyl chloride		ethylenediamine
Compound 297	Methyl 2-amino-5-	4-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	N,N-Diethyl-
	bromobenzoate	benzoyl chloride		ethylenediamine
Compound 298	Methyl 2-amino-5-	4-(Chloromethyl)-	p-Methoxybenzaldehyde	N,N-Diethyl-
	bromobenzoate	benzoyl chloride		ethylenediamine
Compound 299	Methyl 2-amino-5-	4-(Chloromethyl)-	m-Methoxybenzaldehyde	N,N-Diethyl-
	bromobenzoate	benzoyl chloride		ethylenediamine
Compound 300	Methyl 2-amino-5-	4-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	N-(3-Amino-
	bromobenzoate	benzoyl chloride		propyl)di-
				ethanolamine
Compound 301	Methyl 2-amino-5-	4-(Chloromethyl)-	3-Fluorobenzaldehyde	N-(3-Amino-
	bromobenzoate	benzoyl chloride		propyl)di-
				ethanolamine
Compound 302	Methyl 2-amino-5-	4-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	N-(3-Amino-
	bromobenzoate	benzoyl chloride		propyl)di-
				ethanolamine
Compound 303	Methyl 2-amino-5-	4-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	Diisopropanol-
	bromobenzoate	benzoyl chloride		amine
Compound 304	Methyl 2-amino-5-	4-(Chloromethyl)-	p-Tolualdehyde	Diisopropanol-
	bromobenzoate	benzoyl chloride		amine
Compound 305	Methyl 2-amino-5-	4-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	N-(2-(1-
	bromobenzoate	benzoyl chloride		Piperazino)-
				acetyl)-
				morpholine
Compound 306	Methyl 2-amino-5-	4-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	N-(2-(1-
	bromobenzoate	benzoyl chloride		Piperazino)-
				acetyl)-
				morpholine
Compound 307	Methyl 2-amino-5-	4-(Chloromethyl)-	p-Methoxybenzaldehyde	N-(2-(1-
	bromobenzoate	benzoyl chloride		Piperazino)-
				acetyl)-
				morpholine
Compound 308	Methyl 2-amino-5-	4-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	4-Piperidino-
	bromobenzoate	benzoyl chloride		piperidine
Compound 309	Methyl 2-amino-5-	4-(Chloromethyl)-	p-Tolualdehyde	4-Piperidino-
	bromobenzoate	benzoyl chloride		piperidine
Compound 310	Methyl 2-amino-5-	4-(Chloromethyl)-	m-Tolualdehyde	4-Piperidino-
	bromobenzoate	benzoyl chloride		piperidine
Compound 311	Methyl 2-amino-5-	4-(Chloromethyl)-	4-Fluorobenzaldehyde	4-Piperidino-
	bromobenzoate	benzoyl chloride		piperidine
Compound 312	Methyl 2-amino-5-	4-(Chloromethyl)-	3-Fluorobenzaldehyde	4-Piperidino-
	bromobenzoate	benzoyl chloride		piperidine
Compound 313	Methyl 2-amino-5-	4-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	4-Piperidino-
	bromobenzoate	benzoyl chloride		piperidine
Compound 314	Methyl 2-amino-5-	4-(Chloromethyl)-	p-Methoxybenzaldehyde	4-Piperidino-
	bromobenzoate	benzoyl chloride		piperidine
Compound 315	Methyl 2-amino-5-	4-(Chloromethyl)-	m-Methoxybenzaldehyde	4-Piperidino-
	bromobenzoate	benzoyl chloride		piperidine
Compound 316	Methyl 2-amino-5-	4-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	1-(2-Hydroxyethyl)-
	bromobenzoate	benzoyl chloride		piperazine
Compound 317	Methyl 2-amino-5-	4-(Chloromethyl)-	p-Tolualdehyde	1-(2-Hydroxyethyl)-
	bromobenzoate	benzoyl chloride		piperazine
Compound 318	Methyl 2-amino-5-	4-(Chloromethyl)-	m-Tolualdehyde	1-(2-Hydroxyethyl)-
	bromobenzoate	benzoyl chloride		piperazine
Compound 319	Methyl 2-amino-5-	4-(Chloromethyl)-	4-Fluorobenzaldehyde	1-(2-Hydroxyethyl)-
	bromobenzoate	benzoyl chloride		piperazine
Compound 320	Methyl 2-amino-5-	4-(Chloromethyl)-	3-Fluorobenzaldehyde	1-(2-Hydroxyethyl)-
	bromobenzoate	benzoyl chloride		piperazine
Compound 321	Methyl 2-amino-5-	4-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	1-(2-Hydroxyethyl)-
	bromobenzoate	benzoyl chloride		piperazine
Compound 322	Methyl 2-amino-5-	4-(Chloromethyl)-	p-Methoxybenzaldehyde	1-(2-Hydroxyethyl)-
	bromobenzoate	benzoyl chloride		piperazine
Compound 323	Methyl 2-amino-5-	4-(Chloromethyl)-	m-Methoxybenzaldehyde	1-(2-Hydroxyethyl)-
	bromobenzoate	benzoyl chloride
Compound 324	Methyl 2-amino-5-	4-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	4-Hydroxypiperidine
	bromobenzoate	benzoyl chloride
Compound 325	Methyl 2-amino-5-	4-(Chloromethyl)-	p-Tolualdehyde	4-Hydroxypiperidine
	bromobenzoate	benzoyl chloride
Compound 326	Methyl 2-amino-5-	4-(Chloromethyl)-	m-Tolualdehyde	4-Hydroxypiperidine
	bromobenzoate	benzoyl chloride
Compound 327	Methyl 2-amino-5-	4-(Chloromethyl)-	4-Fluorobenzaldehyde	4-Hydroxypiperidine
	bromobenzoate	benzoyl chloride
Compound 328	Methyl 2-amino-5-	4-(Chloromethyl)-	3-Fluorobenzaldehyde	4-Hydroxypiperidine
	bromobenzoate	benzoyl chloride
Compound 329	Methyl 2-amino-5-	4-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	4-Hydroxypiperidine
	bromobenzoate	benzoyl chloride
Compound 330	Methyl 2-amino-5-	4-(Chloromethyl)-	p-Methoxybenzaldehyde	4-Hydroxypiperidine
	bromobenzoate	benzoyl chloride
Compound 331	Methyl 2-amino-5-	4-(Chloromethyl)-	m-Methoxybenzaldehyde	4-Hydroxypiperidine
	bromobenzoate	benzoyl chloride
Compound 332	Methyl 2-amino-5-	4-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	4-Piperidine-
	bromobenzoate	benzoyl chloride		methanol
Compound 333	Methyl 2-amino-5-	4-(Chloromethyl)-	p-Tolualdehyde	4-Piperidine-
	bromobenzoate	benzoyl chloride		methanol
Compound 334	Methyl 2-amino-5-	4-(Chloromethyl)-	m-Tolualdehyde	4-Piperidine-
	bromobenzoate	benzoyl chloride		methanol
Compound 335	Methyl 2-amino-5-	4-(Chloromethyl)-	4-Fluorobenzaldehyde	4-Piperidine-
	bromobenzoate	benzoyl chloride		methanol
Compound 336	Methyl 2-amino-5-	4-(Chloromethyl)-	3-Fluorobenzaldehyde	4-Piperidine-
	bromobenzoate	benzoyl chloride		methanol
Compound 337	Methyl 2-amino-5-	4-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	4-Piperidine-
	bromobenzoate	benzoyl chloride		methanol
Compound 338	Methyl 2-amino-5-	4-(Chloromethyl)-	p-Methoxybenzaldehyde	4-Piperidine-
	bromobenzoate	benzoyl chloride		methanol
Compound 339	Methyl 2-amino-5-	4-(Chloromethyl)-	m-Methoxybenzaldehyde	4-Piperidine-
	bromobenzoate	benzoyl chloride		methanol
Compound 340	Methyl 2-amino-5-	4-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	4-Piperidine-
	bromobenzoate	benzoyl chloride		ethanol
Compound 341	Methyl 2-amino-5-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	3-Mercapto-
	bromobenzoate	benzoyl chloride		1,2,4-triazole
Compound 342	Methyl 3-amino-4-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	N,N-Diethyl-
	methylthiophene-2-	benzoyl chloride		N′-methyl-
	carboxylate			ethylenediamine
Compound 343	Methyl 3-amino-4-	3-(Chloromethyl)-	p-Tolualdehyde	N,N-Diethyl-
	methylthiophene-2-	benzoyl chloride		N′-methyl-
	carboxylate			ethylenediamine
Compound 344	Methyl 3-amino-4-	3-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	N,N-Diethyl-
	methylthiophene-2-	benzoyl chloride		N′-methyl-
	carboxylate			ethylenediamine
Compound 345	Methyl 3-amino-4-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	4-Piperidino-
	methylthiophene-2-	benzoyl chloride		piperidine
	carboxylate
Compound 346	Methyl 2-amino-5-	Nicotinoyl chloride	Trans-
	bromobenzoate	hydrochloride	cinnamaldehyde
Compound 347	Methyl 2-amino-5-	Isonicotinoyl	Trans-
	bromobenzoate	chloride	cinnamaldehyde
		hydrochloride
Compound 348	Methyl 2-amino-5-	Nicotinoyl chloride	Trans-
	chlorobenzoate	hydrochloride	cinnamaldehyde
Compound 349	Methyl 2-amino-5-	Isonicotinoyl	Trans-
	chlorobenzoate	chloride	cinnamaldehyde
		hydrochloride
Compound 350	Methyl 2-amino-5-	Isonicotinoyl	3-(2-Hydroxy-
	bromobenzoate	chloride	ethoxy)-
		hydrochloride	benzaldehyde
Compound 351	Methyl 2-amino-5-	Isonicotinoyl	3-(2-Hydroxy-
	chlorobenzoate	chloride	ethoxy)-
		hydrochloride	benzaldehyde
Compound 352	Methyl 2-amino-5-	Nicotinoyl chloride	2-Methoxy-
	bromobenzoate	hydrochloride	cinnamaldehyde
Compound 353	Methyl 2-amino-5-	Isonicotinoyl	2-Methoxy-
	bromobenzoate	chloride	cinnamaldehyde
		hydrochloride
Compound 354	Methyl 2-amino-5-	Nicotinoyl chloride	2-Methoxy-
	chlorobenzoate	hydrochloride	cinnamaldehyde
Compound 355	Methyl 2-amino-5-	Isonicotinoyl	2-Methoxy-
	chlorobenzoate	chloride	cinnamaldehyde
		hydrochloride
Compound 356	Methyl 2-amino-5-	Picolinoyl chloride	p-Tolualdehyde
	bromobenzoate	hydrochloride
Compound 357	Methyl 2-amino-5-	4-(Chloromethyl)-	m-Tolualdehyde	3-Fluoro-
	bromobenzoate	benzoyl chloride		benzenethiol
Compound 358	Methyl 2-	Nicotinoyl chloride	4-Dimethyl-
	aminobenzoate	hydrochloride	amino-
			cinnamaldehyde
Compound 359	Methyl 2-amino-5-	Picolinoyl chloride	3-Fluorobenzaldehyde
	chlorobenzoate	hydrochloride
Compound 360	Methyl 2-amino-5-	Picolinoyl chloride	4-Fluorobenzaldehyde
	chlorobenzoate	hydrochloride
Compound 361	Methyl 2-amino-5-	Picolinoyl chloride	m-Tolualdehyde
	chlorobenzoate	hydrochloride
Compound 362	Methyl 2-amino-5-	Picolinoyl chloride	p-Tolualdehyde
	chlorobenzoate	hydrochloride
Compound 363	Methyl 2-amino-5-	Picolinoyl chloride	3,4-Dimethylbenzaldehyde
	chlorobenzoate	hydrochloride
Compound 364	Methyl 2-amino-5-	Picolinoyl chloride	4-Chloro-3-trifluoromethylbenzaldehyde
	chlorobenzoate	hydrochloride
Vacant number
Compound 366	Methyl 2-amino-5-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	4-Mercapto-
	chlorobenzoate	benzoyl chloride		pyridine
Compound 367	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	p-Tolualdehyde
	bromobenzoate	chloride
Compound 368	Methyl 2-amino-5-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	4-Piperidino-
	chlorobenzoate	benzoyl chloride		piperidine
Compound 369	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	4-Piperidino-
	chlorobenzoate	benzoyl chloride		piperidine
Compound 370	Methyl 2-amino-5-	3-(Chloromethyl)-	m-Tolualdehyde	4-Piperidino-
	chlorobenzoate	benzoyl chloride		piperidine
Compound 371	Methyl 2-amino-5-	3-(Chloromethyl)-	p-Tolualdehyde	4-Piperidino-
	chlorobenzoate	benzoyl chloride		piperidine
Compound 372	Methyl 2-amino-5-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	4-Piperidino-
	chlorobenzoate	benzoyl chloride		piperidine
Compound 373	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	4-Piperidino-
	chlorobenzoate	benzoyl chloride		piperidine
Compound 374	Methyl 2-amino-5-	3-(Chloromethyl)-	3-Methoxybenzaldehyde	4-Piperidino-
	chlorobenzoate	benzoyl chloride		piperidine
Compound 375	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Methoxybenzaldehyde	4-Piperidino-
	chlorobenzoate	benzoyl chloride		piperidine
Compound 376	Methyl 2-amino-5-	3-(Chloromethyl)-	3-Hydroxybenzaldehyde	4-Piperidino-
	chlorobenzoate	benzoyl chloride		piperidine
Compound 377	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Hydroxybenzaldehyde	4-Piperidino-
	chlorobenzoate	benzoyl chloride		piperidine
Compound 378	Methyl 2-amino-5-	4-(Chloromethyl)-	3-Methoxybenzaldehyde	4-Piperidino-
	bromobenzoate	benzoyl chloride		piperidine
Compound 379	Methyl 2-amino-5-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	N,N-Diethyl-
	chlorobenzoate	benzoyl chloride		N′-methyl-
				ethylenediamine
Compound 380	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	N,N-Diethyl
	chlorobenzoate	benzoyl chloride		N′-methyl-
				ethylenediamine
Compound 381	Methyl 2-amino-5-	3-(Chloromethyl)-	m-Tolualdehyde	N,N-Diethyl-
	chlorobenzoate	benzoyl chloride		N′-methyl-
				ethylenediamine
Compound 382	Methyl 2-amino-5-	3-(Chloromethyl)-	p-Tolualdehyde	N,N-Diethyl-
	chlorobenzoate	benzoyl chloride		N′-methyl-
				ethylenediamine
Compound 383	Methyl 2-amino-5-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	N,N-Diethyl-
	chlorobenzoate	benzoyl chloride		N′-methyl-
				ethylenediamine
Compound 384	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	N,N-Diethyl-
	chlorobenzoate	benzoyl chloride		N′-methyl-
				ethylenediamine
Compound 385	Methyl 2-amino-5-	3-(Chloromethyl)-	3-Methoxybenzaldehyde	N,N-Diethyl-
	chlorobenzoate	benzoyl chloride		N′-methyl-
				ethylenediamine
Compound 386	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Methoxybenzaldehyde	N,N-Diethyl-
	chlorobenzoate	benzoyl chloride		N′-methyl-
				ethylenediamine
Compound 387	Methyl 2-amino-5-	3-(Chloromethyl)-	3-Hydroxybenzaldehyde	N,N-Diethyl-
	chlorobenzoate	benzoyl chloride		N′-methyl-
				ethylenediamine
Compound 388	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Hydroxybenzaldehyde	N,N-Diethyl-
	chlorobenzoate	benzoyl chloride		N′-methyl-
				ethylenediamine
Compound 389	Methyl 2-amino-5-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	3-Mercapto-
	chlorobenzoate	benzoyl chloride		1,2,4-triazole
Compound 390	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	3-Mercapto-
	chlorobenzoate	benzoyl chloride		1,2,4-triazole
Compound 391	Methyl 2-amino-5-	3-(Chloromethyl)-	m-Tolualdehyde	3-Mercapto-
	chlorobenzoate	benzoyl chloride		1,2,4-triazole
Compound 392	Methyl 2-amino-5-	3-(Chloromethyl)-	p-Tolualdehyde	3-Mercapto-
	chlorobenzoate	benzoyl chloride		1,2,4-triazole
Compound 393	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	3-Mercapto-
	chlorobenzoate	benzoyl chloride		1,2,4-triazole
Compound 394	Methyl 2-amino-5-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	2-(Methylamino)
	chlorobenzoate	benzoyl chloride		ethanol
Compound 395	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	2-(Methylamino)
	chlorobenzoate	benzoyl chloride		ethanol
Compound 396	Methyl 2-amino-5-	3-(Chloromethyl)-	m-Tolualdehyde	2-(Methylamino)
	chlorobenzoate	benzoyl chloride		ethanol
Compound 397	Methyl 2-amino-5-	3-(Chloromethyl)-	p-Tolualdehyde	2-(Methylamino)
	chlorobenzoate	benzoyl chloride		ethanol
Compound 398	Methyl 2-amino-5-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	2-(Methylamino)
	chlorobenzoate	benzoyl chloride		ethanol
Compound 399	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	2-(Methylamino)
	chlorobenzoate	benzoyl chloride		ethanol
Compound 400	Methyl 2-amino-5-	3-(Chloromethyl)-	3-Methoxybenzaldehyde	2-(Methylamino)
	chlorobenzoate	benzoyl chloride		ethanol
Compound 401	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Methoxybenzaldehyde	2-(Methylamino)
	chlorobenzoate	benzoyl chloride		ethanol
Compound 402	Methyl 2-amino-5-	3-(Chloromethyl)-	3-Hydroxybenzaldehyde	2-(Methylamino)
	chlorobenzoate	benzoyl chloride		ethanol
Compound 403	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Hydroxybenzaldehyde	2-(Methylamino)
	chlorobenzoate	benzoyl chloride		ethanol
Compound 404	Methyl 2-amino-5-	3-(Chloromethyl)-	m-Tolualdehyde	Diethanolamine
	chlorobenzoate	benzoyl chloride
Compound 405	Methyl 2-amino-5-	3-(Chloromethyl)-	p-Tolualdehyde	Diethanolamine
	chlorobenzoate	benzoyl chloride
Compound 406	Methyl 2-amino-5-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	Diethanolamine
	chlorobenzoate	benzoyl chloride
Compound 407	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	Diethanolamine
	chlorobenzoate	benzoyl chloride
Compound 408	Methyl 2-amino-5-	3-(Chloromethyl)-	3-Methoxybenzaldehyde	Diethanolamine
	chlorobenzoate	benzoyl chloride
Compound 409	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Methoxybenzaldehyde	Diethanolamine
	chlorobenzoate	benzoyl chloride
Compound 410	Methyl 2-amino-5-	3-(Chloromethyl)-	3-Hydroxybenzaldehyde	Diethanolamine
	chlorobenzoate	benzoyl chloride
Compound 411	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Hydroxybenzaldehyde	Diethanolamine
	chlorobenzoate	benzoyl chloride
Compound 412	Methyl 2-amino-5-	4-(Chloromethyl)-	3-Fluorobenzaldehyde	2-(Methylamino)
	chlorobenzoate	benzoyl chloride		ethanol
Compound 413	Methyl 2-amino-5-	4-(Chloromethyl)-	4-Fluorobenzaldehyde	2-(Methylamino)
	chlorobenzoate	benzoyl chloride		ethanol
Compound 414	Methyl 2-amino-5-	4-(Chloromethyl)-	m-Tolualdehyde	2-(Methylamino)
	chlorobenzoate	benzoyl chloride		ethanol
Compound 415	Methyl 2-amino-5-	4-(Chloromethyl)-	p-Tolualdehyde	2-(Methylamino)
	chlorobenzoate	benzoyl chloride		ethanol
Compound 416	Methyl 2-amino-5-	4-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	2-(Methylamino)
	chlorobenzoate	benzoyl chloride		ethanol
Compound 417	Methyl 2-amino-5-	4-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	2-(Methylamino)
	chlorobenzoate	benzoyl chloride		ethanol
Compound 418	Methyl 2-amino-5-	4-(Chloromethyl)-	3-Methoxybenzaldehyde	2-(Methylamino)
	chlorobenzoate	benzoyl chloride		ethanol
Compound 419	Methyl 2-amino-5-	4-(Chloromethyl)-	4-Methoxybenzaldehyde	2-(Methylamino)
	chlorobenzoate	benzoyl chloride		ethanol
Compound 420	Methyl 2-amino-5-	4-(Chloromethyl)-	3-Hydroxybenzaldehyde	2-(Methylamino)
	chlorobenzoate	benzoyl chloride		ethanol
Compound 421	Methyl 2-amino-5-	4-(Chloromethyl)-	4-Hydroxybenzaldehyde	2-(Methylamino)
	chlorobenzoate	benzoyl chloride		ethanol
Compound 422	Methyl 2-amino-5-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	2-(Ethylamino)
	chlorobenzoate	benzoyl chloride		ethanol
Compound 423	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	2-(Ethylamino)
	chlorobenzoate	benzoyl chloride		ethanol
Compound 424	Methyl 2-amino-5-	3-(Chloromethyl)-	m-Tolualdehyde	2-(Ethylamino)
	chlorobenzoate	benzoyl chloride		ethanol
Compound 425	Methyl 2-amino-5-	3-(Chloromethyl)-	p-Tolualdehyde	2-(Ethylamino)
	chlorobenzoate	benzoyl chloride		ethanol
Compound 426	Methyl 2-amino-5-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	2-(Ethylamino)
	chlorobenzoate	benzoyl chloride		ethanol
Compound 427	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	2-(Ethylamino)
	chlorobenzoate	benzoyl chloride		ethanol
Compound 428	Methyl 2-amino-5-	3-(Chloromethyl)-	3-Methoxybenzaldehyde	2-(Ethylamino)
	chlorobenzoate	benzoyl chloride		ethanol
Compound 429	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Methoxybenzaldehyde	2-(Ethylamino)
	chlorobenzoate	benzoyl chloride		ethanol
Compound 430	Methyl 2-amino-5-	3-(Chloromethyl)-	3-Hydroxybenzaldehyde	2-(Ethylamino)
	chlorobenzoate	benzoyl chloride		ethanol
Compound 431	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Hydroxybenzaldehyde	2-(Ethylamino)
	chlorobenzoate	benzoyl chloride		ethanol
Compound 432	Methyl 2-amino-5-	4-(Chloromethyl)-	3-Fluorobenzaldehyde	2-(Ethylamino)
	chlorobenzoate	benzoyl chloride		ethanol
Compound 433	Methyl 2-amino-5-	4-(Chloromethyl)-	4-Fluorobenzaldehyde	2-(Ethylamino)
	chlorobenzoate	benzoyl chloride		ethanol
Compound 434	Methyl 2-amino-5-	4-(Chloromethyl)-	m-Tolualdehyde	2-(Ethylamino)
	chlorobenzoate	benzoyl chloride		ethanol
Compound 435	Methyl 2-amino-5-	4-(Chloromethyl)-	p-Tolualdehyde	2-(Ethylamino)
	chlorobenzoate	benzoyl chloride		ethanol
Compound 436	Methyl 2-amino-5-	4-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	2-(Ethylamino)
	chlorobenzoate	benzoyl chloride		ethanol
Compound 437	Methyl 2-amino-5-	4-(Chloromethyl)-	4-Chloro-3-	2-(Ethylamino)
	chlorobenzoate	benzoyl chloride	trifluoromethylbenzaldehyde	ethanol
Compound 438	Methyl 2-amino-5-	4-(Chloromethyl)-	3-Methoxybenzaldehyde	2-(Ethylamino)
	chlorobenzoate	benzoyl chloride		ethanol
Compound 439	Methyl 2-amino-5-	4-(Chloromethyl)-	4-Methoxybenzaldehyde	2-(Ethylamino)
	chlorobenzoate	benzoyl chloride		ethanol
Compound 440	Methyl 2-amino-5-	4-(Chloromethyl)-	3-Hydroxybenzaldehyde	2-(Ethylamino)
	chlorobenzoate	benzoyl chloride		ethanol
Compound 441	Methyl 2-amino-5-	4-(Chloromethyl)-	4-Hydroxybenzaldehyde	2-(Ethylamino)
	chlorobenzoate	benzoyl chloride		ethanol
Compound 442	Methyl 2-amino-5-	4-(Chloromethyl)-	3-Fluorobenzaldehyde	2-Diethylamino-
	chlorobenzoate	benzoyl chloride		ethanethiol
				hydrochloride
Compound 443	Methyl 2-amino-5-	4-(Chloromethyl)-	4-Fluorobenzaldehyde	2-Diethylamino-
	chlorobenzoate	benzoyl chloride		ethanethiol
				hydrochloride
Compound 444	Methyl 2-amino-5-	4-(Chloromethyl)-	m-Tolualdehyde	2-Diethylamino-
	chlorobenzoate	benzoyl chloride		ethanethiol
				hydrochloride
Compound 445	Methyl 2-amino-5-	4-(Chloromethyl)-	p-Tolualdehyde	2-Diethylamino-
	chlorobenzoate	benzoyl chloride		ethanethiol
				hydrochloride
Compound 446	Methyl 2-amino-5-	4-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	2-Diethylamino-
	chlorobenzoate	benzoyl chloride		ethanethiol
				hydrochloride
Compound 447	Methyl 2-amino-5-	4-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	2-Diethylamino-
	chlorobenzoate	benzoyl chloride		ethanethiol
				hydrochloride
Compound 448	Methyl 2-amino-5-	4-(Chloromethyl)-	3-Methoxybenzaldehyde	2-Diethylamino-
	chlorobenzoate	benzoyl chloride		ethanethiol
				hydrochloride
Compound 449	Methyl 2-amino-5-	4-(Chloromethyl)-	4-Methoxybenzaldehyde	2-Diethylamino-
	chlorobenzoate	benzoyl chloride		ethanethiol
				hydrochloride
Compound 450	Methyl 2-amino-5-	4-(Chloromethyl)-	3-Hydroxybenzaldehyde	2-Diethylamino-
	chlorobenzoate	benzoyl chloride		ethanethiol
				hydrochloride
Compound 451	Methyl 2-amino-5-	4-(Chloromethyl)-	4-Hydroxybenzaldehyde	2-Diethylamino-
	chlorobenzoate	benzoyl chloride		ethanethiol
				hydrochloride
Compound 452	Methyl 2-amino-5-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	2-Diethylamino-
	chlorobenzoate	benzoyl chloride		ethanethiol
				hydrochloride
Compound 453	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	2-Diethylamino-
	chlorobenzoate	benzoyl chloride		ethanethiol
				hydrochloride
Compound 454	Methyl 2-amino-5-	3-(Chloromethyl)-	m-Tolualdehyde	2-Diethylamino-
	chlorobenzoate	benzoyl chloride		ethanethiol
				hydrochloride
Compound 455	Methyl 2-amino-5-	3-(Chloromethyl)-	p-Tolualdehyde	2-Diethylamino-
	chlorobenzoate	benzoyl chloride		ethanethiol
				hydrochloride
Compound 456	Methyl 2-amino-5	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	2-Diethylamino-
	chlorobenzoate	benzoyl chloride		ethanethiol
				hydrochloride
Compound 457	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Chloro-3-	2-Diethylamino-
	chlorobenzoate	benzoyl chloride	trifluoromethylbenzaldehyde	ethanethiol
				hydrochloride
Compound 458	Methyl 2-amino-5-	3-(Chloromethyl)-	3-Methoxybenzaldehyde	2-Diethylamino-
	chlorobenzoate	benzoyl chloride		ethanethiol
				hydrochloride
Compound 459	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Methoxybenzaldehyde	2-Diethylamino-
	chlorobenzoate	benzoyl chloride		ethanethiol
				hydrochloride
Compound 460	Methyl 2-amino-5-	3-(Chloromethyl)-	3-Hydroxybenzaldehyde	2-Diethylamino-
	chlorobenzoate	benzoyl chloride		ethanethiol
				hydrochloride
Compound 461	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Hydroxybenzaldehyde	2-Diethylamino-
	chlorobenzoate	benzoyl chloride		ethanethiol
				hydrochloride
Compound 462	Methyl 2-amino-5-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	1-(2-Dimethylaminoethyl)-
	chlorobenzoate	benzoyl chloride		5-mercapto-
				tetrazole
Compound 463	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	1-(2-Dimethylaminoethyl)-
	chlorobenzoate	benzoyl chloride		5-mercapto-
				tetrazole
Compound 464	Methyl 2-amino-5-	3-(Chloromethyl)-	m-Tolualdehyde	1-(2-Dimethyl aminoethyl)-
	chlorobenzoate	benzoyl chloride		5-mercapto-
				tetrazole
Compound 465	Methyl 2-amino-5-	3-(Chloromethyl)-	p-Tolualdehyde	1-(2-Dimethylaminoethyl)-
	chlorobenzoate	benzoyl chloride		5-mercapto-
				tetrazole
Compound 466	Methyl 2-amino-5-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	1-(2-Dimethylaminoethyl)-
	chlorobenzoate	benzoyl chloride		5-mercapto-
				tetrazole
Compound 467	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	1-(2-Dimethylaminoethyl)-
	chlorobenzoate	benzoyl chloride		5-mercapto-
				tetrazole
Compound 468	Methyl 2-amino-5-	3-(Chloromethyl)-	3-Methoxybenzaldehyde	1(2-Dimethylaminoethyl)-
	chlorobenzoate	benzoyl chloride		5-mercapto-
				tetrazole
Compound 469	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Methoxybenzaldehyde	1-(2-Dimethylaminoethyl)-
	chlorobenzoate	benzoyl chloride		5-mercapto-
				tetrazole
Compound 470	Methyl 2-amino-5-	3-(Chloromethyl)-	3-Hydroxybenzaldehyde	1-(2-Dimethylaminoethyl)-
	chlorobenzoate	benzoyl chloride		5-mercapto-
				tetrazole
Compound 471	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Hydroxybenzaldehyde	1-(2-Dimethylaminoethyl)-
	chlorobenzoate	benzoyl chloride		5-mercapto-
				tetrazole
Compound 472	Methyl 2-amino-5-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	N,N-Diethyl-
	iodobenzoate	benzoyl chloride		N′-methyl-
				ethylenediamine
Compound 473	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	N,N-Diethyl-
	iodobenzoate	benzoyl chloride		N′-methyl-
				ethylenediamine
Compound 474	Methyl 2-amino-5-	3-(Chloromethyl)-	m-Tolualdehyde	N,N-Diethyl-
	iodobenzoate	benzoyl chloride		N′-methyl-
				ethylenediamine
Compound 475	Methyl 2-amino-5-	3-(Chloromethyl)-	p-Tolualdehyde	N,N-Diethyl-
	iodobenzoate	benzoyl chloride		N′-methyl-
				ethylenediamine
Compound 476	Methyl 2-amino-5-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	N,N-Diethyl-
	iodobenzoate	benzoyl chloride		N′-methyl-
				ethylenediamine
Compound 477	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	N,N-Diethyl-
	iodobenzoate	benzoyl chloride		N′-methyl-
				ethylenediamine
Compound 478	Methyl 2-amino-5-	3-(Chloromethyl)-	3-Methoxybenzaldehyde	N,N-Diethyl-
	iodobenzoate	benzoyl chloride		N′-methyl-
				ethylenediamine
Compound 479	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Methoxybenzaldehyde	N,N-Diethyl
	iodobenzoate	benzoyl chloride		N′-methyl-
				ethylenediamine
Compound 480	Methyl 2-amino-5-	3-(Chloromethyl)-	3-Hydroxybenzaldehyde	N,N-Diethyl-
	iodobenzoate	benzoyl chloride		N′-methyl-
				ethylenediamine
Compound 481	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Hydroxybenzaldehyde	N,N-Diethyl-
	iodobenzoate	benzoyl chloride		N′-methyl-
				ethylenediamine
Compound 482	Methyl 2-amino-5-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	4-Piperidino-
	iodobenzoate	benzoyl chloride		piperidine
Compound 483	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	4-Piperidino-
	iodobenzoate	benzoyl chloride		piperidine
Compound 484	Methyl 2-amino-5-	3-(Chloromethyl)-	m-Tolualdehyde	4-Piperidino-
	iodobenzoate	benzoyl chloride		piperidine
Compound 485	Methyl 2-amino-5-	3-(Chloromethyl)-	p-Tolualdehyde	4-Piperidino-
	iodobenzoate	benzoyl chloride		piperidine
Compound 486	Methyl 2-amino-5-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	4-Piperidino-
	iodobenzoate	benzoyl chloride		piperidine
Compound 487	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	4-Piperidino-
	iodobenzoate	benzoyl chloride		piperidine
Compound 488	Methyl 2-amino-5-	3-(Chloromethyl)-	3-Methoxybenzaldehyde	4-Piperidino-
	iodobenzoate	benzoyl chloride		piperidine
Compound 489	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Methoxybenzaldehyde	4-Piperidino-
	iodobenzoate	benzoyl chloride		piperidine
Compound 490	Methyl 2-amino-5-	3-(Chloromethyl)-	3-Hydroxybenzaldehyde	4-Piperidino-
	iodobenzoate	benzoyl chloride		piperidine
Compound 491	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Hydroxybenzaldehyde	4-Piperidino-
	iodobenzoate	benzoyl chloride		piperidine
Compound 492	Methyl 2-amino-5-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	2-Mercapto-
	chlorobenzoate	benzoyl chloride		ethanol
Compound 493	Methyl 2-amino-5-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	2-Mercapto-
	chlorobenzoate	benzoyl chloride		ethanol
Compound 494	Methyl 2-amino-5-	4-Methylbenzoyl	p-Tolualdehyde
	bromobenzoate	chloride
Compound 495	Methyl 2-amino-5-	Picolinoyl chloride	3-Fluorobenzaldehyde
	bromobenzoate	hydrochloride
Compound 496	Methyl 2-amino-5-	Picolinoyl chloride	4-Fluorobenzaldehyde
	bromobenzoate	hydrochloride
Compound 497	Methyl 2-amino-5-	Picolinoyl chloride	m-Tolualdehyde
	bromobenzoate	hydrochloride
Compound 498	Methyl 2-amino-5-	Picolinoyl chloride	p-Tolualdehyde
	bromobenzoate	hydrochloride
Compound 499	Methyl 2-amino-5-	Picolinoyl chloride	3,4-Dimethylbenzaldehyde
	bromobenzoate	hydrochloride
Compound 500	Methyl 2-amino-5-	Picolinoyl chloride	4-Chloro-3-trifluoromethylbenzaldehyde
	bromobenzoate	hydrochloride
Compound 501	Methyl 2-amino-5-	4-Ethoxybenzoyl	3-Fluorobenzaldehyde
	bromobenzoate	chloride
Compound 502	Methyl 2-amino-5-	4-Ethoxybenzoyl	4-Fluorobenzaldehyde
	bromobenzoate	chloride
Compound 503	Methyl 2-amino-5-	4-Ethoxybenzoyl	p-Tolualdehyde
	bromobenzoate	chloride
Compound 504	Methyl 2-amino-5-	4-Ethoxybenzoyl	3,4-Dimethylbenzaldehyde
	bromobenzoate	chloride
Compound 505	Methyl 2-	Picolinoyl chloride	3-Fluorobenzaldehyde
	aminobenzoate	hydrochloride
Compound 506	Methyl 2-	Picolinoyl chloride	4-Fluorobenzaldehyde
	aminobenzoate	hydrochloride
Compound 507	Methyl 2-	Picolinoyl chloride	3,4-Dimethylbenzaldehyde
	aminobenzoate	hydrochloride
Compound 508	Methyl 2-	Picolinoyl chloride	4-Chloro-3-trifluoromethylbenzaldehyde
	aminobenzoate	hydrochloride
Compound 509	Methyl 2-amino-5-	Cyclohexane-	3-Fluorobenzaldehyde
	bromobenzoate	carbonyl chloride
Compound 510	Methyl 2-amino-5-	Isoxazole-5-	3-Fluorobenzaldehyde
	bromobenzoate	carbonyl chloride
Compound 511	Methyl 2-amino-5-	Isoxazole-5-	m-Tolualdehyde
	bromobenzoate	carbonyl chloride
Compound 512	Methyl 2-amino-5-	Isoxazole-5-	3,4-Dimethylbenzaldehyde
	bromobenzoate	carbonyl chloride
Compound 513	Methyl 2-amino-5-	Isoxazole-5-	4-Chloro-3-trifluoromethylbenzaldehyde
	bromobenzoate	carbonyl chloride
Compound 514	Methyl 2-	2,5-Dimethylfuran-	3-Fluorobenzaldehyde
	aminobenzoate	3-carbonyl
		chloride
Compound 515	Methyl 2-	2,5-Dimethylfuran-	4-Fluorobenzaldehyde
	aminobenzoate	3-carbonyl
		chloride
Compound 516	Methyl 2-	2,5-Dimethylfuran-	m-Tolualdehyde
	aminobenzoate	3-carbonyl
		chloride
Compound 517	Ethyl 2-amino-4-	3,4-Dimethoxybenzoyl	3-Fluorobenzaldehyde
	methylthiophene-3-	chloride
	carboxylate
Compound 518	Ethyl 2-amino-4-	3,4-Dimethoxybenzoyl	m-Tolualdehyde
	methylthiophene-3-	chloride
	carboxylate
Compound 519	Ethyl 2-amino-4-	3,4-Dimethoxybenzoyl	p-Tolualdehyde
	methylthiophene-3-	chloride
	carboxylate
Vacant number
Compound 521	Ethyl 2-amino-4-	3,4-Dimethoxybenzoyl	3,4-Dimethylbenzaldehyde
	methylthiophene-3-	chloride
	carboxylate
Compound 522	Ethyl 2-amino-4-	3,4-Dimethoxybenzoyl	4-Chloro-3-trifluoromethylbenzaldehyde
	methylthiophene-3-	chloride
	carboxylate
Compound 523	Methyl 3-amino-4-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	3-Mercapto-
	methylthiophene-2-	benzoyl chloride		1,2,4-triazole
	carboxylate
Compound 524	Methyl 3-amino-4-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	3-Mercapto-
	methylthiophene-2-	benzoyl chloride		1,2,4-triazole
	carboxylate
Compound 525	Methyl 3-amino-4-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	3-Mercapto-1-
	methylthiophene-2-	benzoyl chloride		propanol
	carboxylate
Compound 526	Methyl 3-amino-4-	3-(chloromethyl)-	p-Tolualdehyde	3-Mercapto-1-
	methylthiophene-2-	benzoyl chloride		propanol
	carboxylate
Compound 527	Methyl 3-amino-4-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	3-Mercapto-1-
	methylthiophene-2-	benzoyl chloride		propanol
	carboxylate
Compound 528	Methyl 3-amino-4-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	N,N-Diethyl-
	methylthiophene-2-	benzoyl chloride		N′-methyl-
	carboxylate			ethylenediamine
Compound 529	Methyl 3-amino-4-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	N,N-Diethyl-
	methylthiophene-2-	benzoyl chloride		N′-methyl-
	carboxylate			ethylenediamine
Compound 530	Methyl 3-amino-4-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	N,N-Diethyl-
	methylthiophene-2-	benzoyl chloride		N′-methyl-
	carboxylate			ethylenediamine
Compound 531	Methyl 3-amino-4-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	4-Piperidino-
	methylthiophene-2-	benzoyl chloride		piperidine
	carboxylate
Compound 532	Methyl 3-amino-4-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	1-(2-Hydroxyethyl)-
	methylthiophene-2-	benzoyl chloride		piperazine
	carboxylate
Compound 533	Methyl 3-amino-4-	3-(Chloromethyl)-	p-Tolualdehyde	1-(2-Hydroxyethyl)-
	methylthiophene-2-	benzoyl chloride		piperazine
	carboxylate
Compound 534	Methyl 3-amino-4-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	1-(2-
	methylthiophene-2-	benzoyl chloride		Hydroxyethyl)
	carboxylate			piperazine
Compound 535	Methyl 3-amino-4-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	1-(2-
	methylthiophene-2-	benzoyl chloride		Hydroxyethyl)
	carboxylate			piperazine
Compound 536	Methyl 3-amino-4-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	N,N-Diethyl-
	methylthiophene-2-	benzoyl chloride		ethylenediamine
	carboxylate
Compound 537	Methyl 3-amino-4-	3-(Chloromethyl)-	p-Tolualdehyde	N,N-Diethyl-
	methylthiophene-2-	benzoyl chloride		ethylenediamine
	carboxylate
Compound 538	Methyl 3-amino-4-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	N,N-Diethyl-
	methylthiophene-2-	benzoyl chloride		ethylenediamine
	carboxylate
Compound 539	Methyl 3-amino-4-	3-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	N,N-Diethyl-
	methylthiophene-2-	benzoyl chloride		ethylenediamine
	carboxylate
Compound 540	Methyl 3-amino-4-	3-(Chloromethyl)-	p-Tolualdehyde	Diisopropanolamine
	methylthiophene-2-	benzoyl chloride
	carboxylate
Compound 541	Methyl 3-amino-4-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	4-Hydroxypiperidine
	methylthiophene-2-	benzoyl chloride
	carboxylate
Compound 542	Methyl 3-amino-4-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	4-Hydroxypiperidine
	methylthiophene-2-	benzoyl chloride
	carboxylate
Compound 543	Methyl 3-amino-4-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	4-Hydroxypiperidine
	methylthiophene-2-	benzoyl chloride
	carboxylate
Compound 544	Methyl 2-amino-5-	Picolinoyl chloride	p-Tolualdehyde
	bromobenzoate	hydrochloride
Compound 545	Methyl 2-	Isonicotinoyl	p-Tolualdehyde
	aminobenzoate	chloride
		hydrochloride
Compound 546	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	2-Mercapto-
	bromobenzoate	benzoyl chloride		ethanol
Compound 547	Methyl 2-amino-5-	3-(Chloromethyl)-	p-Tolualdehyde	2-Mercapto-
	chlorobenzoate	benzoyl chloride		ethanol
Compound 548	Methyl 2-amino-5-	3,4-Dimethoxybenzoyl	3,4-Dimethylbenzaldehyde
	bromobenzoate	chloride
Compound 549	Methyl 2-amino-5-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	Diethanolamine
	chlorobenzoate	benzoyl chloride
Compound 550	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Fluorobenaldehyde	Diethanolamine
	chlorobenzoate	benzoyl chloride
Compound 551	Ethyl 2-amino-4-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	3-Mercapto-
	methylthiophene-3-	benzoyl chloride		1,2,4-triazole
	carboxylate
Compound 552	Ethyl 2-amino-4-	3-(Chloromethyl)-	p-Tolualdehyde	3-Mercapto-
	methylthiophene-3-	benzoyl chloride		1,2,4-triazole
	carboxylate
Compound 553	Ethyl 2-amino-4-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	3-Mercapto-
	methylthiophene-3-	benzoyl chloride		1,2,4-triazole
	carboxylate
Compound 554	Ethyl 2-amino-4-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	3-Mercapto-
	methylthiophene-3-	benzoyl chloride		1,2,4-triazole
	carboxylate
Compound 555	Ethyl 2-amino-4-	3-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	3-Mercapto-
	methylthiophene-3-	benzoyl chloride		1,2,4-triazole
	carboxylate
Compound 556	Ethyl 2-amino-4-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	3-Mercapto-
	methylthiophene-3-	benzoyl chloride		1,2,4-triazole
	carboxylate
Compound 557	Ethyl 2-amino-4-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	3-Mercapto-1-
	methylthiophene-3-	benzoyl chloride		propanol
	carboxylate
Compound 558	Ethyl 2-amino-4-	3-(Chloromethyl)-	p-Tolualdehyde	3-Mercapto-1-
	methylthiophene-3-	benzoyl chloride		propanol
	carboxylate
Compound 559	Ethyl 2-amino-4-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	3-Mercapto-1-
	methylthiophene-3-	benzoyl chloride		propanol
	carboxylate
Compound 560	Ethyl 2-amino-4-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	3-Mercapto-1-
	methylthiophene-3-	benzoyl chloride		propanol
	carboxylate
Compound 561	Ethyl 2-amino-4-	3-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	3-Mercapto-1-
	methylthiophene-3-	benzoyl chloride		propanol
	carboxylate
Compound 562	Ethyl 2-amino-4-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	3-Mercapto-1-
	methylthiophene-3-	benzoyl chloride		propanol
	carboxylate
Compound 563	Ethyl 2-amino-4-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	N,N-Diethyl-
	methylthiophene-3-	benzoyl chloride		N′-methylethylenediamine
	carboxylate
Compound 564	Ethyl 2-amino-4-	3-(Chloromethyl)-	p-Tolualdehyde	N,N-Diethyl-
	methylthiophene-3-	benzoyl chloride		N′-methylethylenediamine
	carboxylate
Compound 565	Ethyl 2-amino-4-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	N,N-Diethyl-
	methylthiophene-3-	benzoyl chloride		N′-methylethylenediamine
	carboxylate
Compound 566	Ethyl 2-amino-4-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	N,N-Diethyl-
	methylthiophene-3-	benzoyl chloride		N′-methylethylenediamine
	carboxylate
Compound 567	Ethyl 2-amino-4-	3-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	N,N-Diethyl-
	methylthiophene-3-	benzoyl chloride		N′-methylethylenediamine
	carboxylate
Compound 568	Ethyl 2-amino-4-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	N,N-Diethyl-
	methylthiophene-3-	benzoyl chloride		N′-methylethylenediamine
	carboxylate
Compound 569	Ethyl 2-amino-4-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	4-Piperidino-
	methylthiophene-3-	benzoyl chloride		piperidine
	carboxylate
Compound 570	Ethyl 2-amino-4-	3-(Chloromethyl)-	p-Tolualdehyde	4-Piperidino-
	methylthiophene-3-	benzoyl chloride		piperidine
	carboxylate
Compound 571	Ethyl 2-amino-4-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	4-Piperidino-
	methylthiophene-3-	benzoyl chloride		piperidine
	carboxylate
Compound 572	Ethyl 2-amino-4-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	4-Pipendino-
	methylthiophene-3-	benzoyl chloride		piperidine
	carboxylate
Compound 573	Ethyl 2-amino-4-	3-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	4-Piperidino-
	methylthiophene-3-	benzoyl chloride		piperidine
	carboxylate
Compound 574	Ethyl 2-amino-4-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	4-Piperidino-
	methylthiophene-3-	benzoyl chloride		piperidine
	carboxylate
Compound 575	Ethyl 2-amino-4-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	1-(2-Hydroxyethyl)-
	methylthiophene-3-	benzoyl chloride		piperazine
	carboxylate
Compound 576	Ethyl 2-amino-4-	3-(Chloromethyl)-	p-Tolualdehyde	1-(2-Hydroxyethyl)-
	methylthiophene-3-	benzoyl chloride		piperazine
	carboxylate
Compound 577	Ethyl 2-amino-4-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	1-(2-Hydroxyethyl)-
	methylthiophene-3-	benzoyl chloride		piperazine
	carboxylate
Compound 578	Ethyl 2-amino-4-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	1-(2-Hydroxyethyl)-
	methylthiophene-3-	benzoyl chloride		piperazine
	carboxylate
Compound 579	Ethyl 2-amino-4-	3-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	1-(2-Hydroxyethyl)-
	methylthiophene-3-	benzoyl chloride		piperazine
	carboxylate
Compound 580	Ethyl 2-amino-4-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	1-(2-Hydroxyethyl)-
	methylthiophene-3-	benzoyl chloride		piperazine
	carboxylate
Compound 581	Ethyl 2-amino-4-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	N,N-Diethylethylenediamine
	methylthiophene-3-	benzoyl chloride
	carboxylate
Compound 582	Ethyl 2-amino-4-	3-(Chloromethyl)-	p-Tolualdehyde	N,N-Diethylethylenediamine
	methylthiophene-3-	benzoyl chloride
	carboxylate
Compound 583	Ethyl 2-amino-4-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	N,N-Diethylethylenediamine
	methylthiophene-3-	benzoyl chloride
	carboxylate
Compound 584	Ethyl 2-amino-4-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	N,N-Diethylethylenediamine
	methylthiophene-3-	benzoyl chloride
	carboxylate
Compound 585	Ethyl 2-amino-4-	3-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	N,N-Diethyl-
	methylthiophene-3-	benzoyl chloride		ethylenediamine
	carboxylate
Compound 586	Ethyl 2-amino-4-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	N,N-Diethyl-
	methylthiophene-3-	benzoyl chloride		ethylenediamine
	carboxylate
Compound 587	Ethyl 2-amino-4-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	Diisopropanolamine
	methylthiophene-3-	benzoyl chloride
	carboxylate
Compound 588	Ethyl 2-amino-4-	3-(Chloromethyl)-	p-Tolualdehyde	Diisopropanolamine
	methylthiophene-3-	benzoyl chloride
	carboxylate
Compound 589	Ethyl 2-amino-4-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	Diisopropanolamine
	methylthiophene-3-	benzoyl chloride
	carboxylate
Compound 590	Ethyl 2-amino-4-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	Diisopropanolamine
	methylthiophene-3-	benzoyl chloride
	carboxylate
Compound 591	Ethyl 2-amino-4-	3-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	Diisopropanolamine
	methylthiophene-3-	benzoyl chloride
	carboxylate
Compound 592	Ethyl 2-amino-4-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	Diisopropanolamine
	methylthiophene-3-	benzoyl chloride
	carboxylate
Compound 593	Ethyl 2-amino-4-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	4-Hydroxypiperidine
	methylthiophene-3-	benzoyl chloride
	carboxylate
Compound 594	Ethyl 2-amino-4-	3-(Chloromethyl)-	p-Tolualdehyde	4-Hydroxypiperidine
	methylthiophene-3-	benzoyl chloride
	carboxylate
Compound 595	Ethyl 2-amino-4-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	4-Hydroxypiperidine
	methylthiophene-3-	benzoyl chloride
	carboxylate
Compound 596	Ethyl 2-amino-4-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	4-Hydroxypiperidine
	methylthiophene-3-	benzoyl chloride
	carboxylate
Compound 597	Ethyl 2-amino-4-	3-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	4-Hydroxypiperidine
	methylthiophene-3-	benzoyl chloride
	carboxylate
Compound 598	Ethyl 2-amino-4-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	4-Hydroxypiperidine
	methylthiophene-3-	benzoyl chloride
	carboxylate
Compound 599	Ethyl 2-amino-4-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	4-Piperidine-
	methylthiophene-3-	benzoyl chloride		methanol
	carboxylate
Compound 600	Ethyl 2-amino-4-	3-(Chloromethyl)-	p-Tolualdehyde	4-Piperidine-
	methylthiophene-3-	benzoyl chloride		methanol
	carboxylate
Compound 601	Ethyl 2-amino-4-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	4-Piperidine-
	methylthiophene-3-	benzoyl chloride		methanol
	carboxylate
Compound 602	Ethyl 2-amino-4-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	4-Piperidine-
	methylthiophene-3-	benzoyl chloride		methanol
	carboxylate
Compound 603	Ethyl 2-amino-4-	3-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	4-Piperidine-
	methylthiophene-3-	benzoyl chloride		methanol
	carboxylate
Compound 604	Ethyl 2-amino-4-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	4-Piperidine-
	methylthiophene-3-	benzoyl chloride		methanol
	carboxylate
Compound 605	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	3-Mercapto-1-
	hydrobenzothiophene-	benzoyl chloride		propanol
	3-carboxylic acid ethyl
	ester
Compound 606	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	3-Mercapto-1-
	hydrobenzothiophene-	benzoyl chloride		propanol
	3-carboxylic acid ethyl
	ester
Compound 607	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	3-Mercapto-1-
	hydrobenzothiophene-	benzoyl chloride		propanol
	3-carboxylic acid ethyl
	ester
Compound 608	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	3-Mercapto-1-
	hydrobenzothiophene-	benzoyl chloride		propanol
	3-carboxylic acid ethyl
	ester
Compound 609	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	N,N-Diethyl-
	hydrobenzothiophene-	benzoyl chloride		N′-methylethylenediamine
	3-carboxylic acid ethyl
	ester
Compound 610	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	p-Tolualdehyde	N,N-Diethyl-
	hydrobenzothiophene-	benzoyl chloride		N′-methylethylenediamine
	3-carboxylic acid ethyl
	ester
Compound 611	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	N,N-Diethyl-
	hydrobenzothiophene-	benzoyl chloride		N′-methylethylenediamine
	3-carboxylic acid ethyl
	ester
Compound 612	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	N,N-Diethyl-
	hydrobenzothiophene-	benzoyl chloride		N′-methylethylenediamine
	3-carboxylic acid ethyl
	ester
Compound 613	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	N,N-Diethyl-
	hydrobenzothiophene-	benzoyl chloride		N′-methylethylenediamine
	3-carboxylic acid ethyl
	ester
Compound 614	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	N,N-Diethyl-
	hydrobenzothiophene-	benzoyl chloride		N′-methylethylenediamine
	3-carboxylic acid ethyl
	ester
Compound 615	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	4-Piperidino-
	hydrobenzothiophene-	benzoyl chloride		piperidine
	3-carboxylic acid ethyl
	ester
Compound 616	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	p-Tolualdehyde	4-Piperidino-
	hydrobenzothiophene-	benzoyl chloride		piperidine
	3-carboxylic acid ethyl
	ester
Compound 617	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	4-Piperidino-
	hydrobenzothiophene-	benzoyl chloride		piperidine
	3-carboxylic acid ethyl
	ester
Compound 618	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	4-Piperidino-
	hydrobenzothiophene-	benzoyl chloride		piperidine
	3-carboxylic acid ethyl
	ester
Compound 619	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	4-Piperidino-
	hydrobenzothiophene-	benzoyl chloride		piperidine
	3-carboxylic acid ethyl
	ester
Compound 620	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	4-Piperidino-
	hydrobenzothiophene-	benzoyl chloride		piperidine
	3-carboxlic acid ethyl
	ester
Compound 621	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	4-Piperazine-
	hydrobenzothiophene-	benzoyl chloride		ethanol
	3-carboxylic acid ethyl
	ester
Compound 622	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	p-Tolualdehyde	4-Piperazine-
	hydrobenzothiophene-	benzoyl chloride		ethanol
	3-carboxylic acid ethyl
	ester
Compound 623	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	4-Piperazine-
	hydrobenzothiophene-	benzoyl chloride		ethanol
	3-carboxylic acid ethyl
	ester
Compound 624	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	4-Piperazine-
	hydrobenzothiophene-	benzoyl chloride		ethanol
	3-carboxylic acid ethyl
	ester
Compound 625	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	4-Piperazine-
	hydrobenzothiophene-	benzoyl chloride		ethanol
	3-carboxylic acid ethyl
	ester
Compound 626	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	4-Piperazine-
	hydrobenzothiophene-	benzoyl chloride		ethanol
	3-carboxylic acid ethyl
	ester
Compound 627	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	Diisopropanolamine
	hydrobenzothiophene-	benzoyl chloride
	3-carboxylic acid ethyl
	ester
Compound 628	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	p-Tolualdehyde	Diisopropanolamine
	hydrobenzothiophene-	benzoyl chloride
	3-carboxylic acid ethyl
	ester
Compound 629	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	Diisopropanolamine
	hydrobenzothiophene-	benzoyl chloride
	3-carboxylic acid ethyl
	ester
Compound 630	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	Diisopropanolamine
	hydrobenzothiophene-	benzoyl chloride
	3-carboxylic acid ethyl
	ester
Compound 631	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	4-Chloro-3-	Diisopropanolamine
	hydrobenzothiophene-	benzoyl chloride	trifluoromethylbenzaldehyde
	3-carboxylic acid ethyl
	ester
Compound 632	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	Diisopropanolamine
	hydrobenzothiophene-	benzoyl chloride
	3-carboxylic acid ethyl
	ester
Compound 633	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	4-Hydroxypiperidine
	hydrobenzothiophene-	benzoyl chloride
	3-carboxylic acid ethyl
	ester
Compound 634	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	p-Tolualdehyde	4-Hydroxypiperidine
	hydrobenzothiophene-	benzoyl chloride
	3-carboxylic acid ethyl
	ester
Compound 635	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	4-Hydroxypiperidine
	hydrobenzothiophene-	benzoyl chloride
	3-carboxylic acid ethyl
	ester
Compound 636	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	4-Hydroxypiperidine
	hydrobenzothiophene-	benzoyl chloride
	3-carboxylic acid ethyl
	ester
Compound 637	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	4-Hydroxypiperidine
	hydrobenzothiophene-	benzoyl chloride
	3-carboxylic acid ethyl
	ester
Compound 638	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	4-Hydroxypiperidine
	hydrobenzothiophene-	benzoyl chloride
	3-carboxylic acid ethyl
	ester
Compound 639	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	4-Piperidine-
	hydrobenzothiophene-	benzoyl chloride		methanol
	3-carboxylic acid ethyl
	ester
Compound 640	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	p-Tolualdehyde	4-Piperidine-
	hydrobenzothiophene-	benzoyl chloride		methanol
	3-carboxylic acid ethyl
	ester
Compound 641	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	4-Piperidine-
	hydrobenzothiophene-	benzoyl chloride		methanol
	3-carboxylic acid ethyl
	ester
Compound 642	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	4-Piperidine-
	hydrobenzothiophene-	benzoyl chloride		methanol
	3-carboxylic acid ethyl
	ester
Compound 643	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	4-Piperidine-
	hydrobenzothiophene-	benzoyl chloride		methanol
	3-carboxylic acid ethyl
	ester
Compound 644	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	4-Piperidine-
	hydrobenzothiophene-	benzoyl chloride		methanol
	3-carboxylic acid ethyl
	ester
Compound 645	Ethyl 2-amino-4-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	3-Mercapto-1-
	methylthiophene-3-	benzoyl chloride		propanol
	carboxylate
Compound 646	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	3-Mercapto-
	hydrobenzothiophene-	benzoyl chloride		1,2,4-triazole
	3-carboxylic acid ethyl
	ester
Compound 647	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	p-Tolualdehyde	3-Mercapto-
	hydrobenzothiophene-	benzoyl chloride		1,2,4-triazole
	3-carboxylic acid ethyl
	ester
Compound 648	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	3-Mercapto-
	hydrobenzothiophene-	benzoyl chloride		1,2,4-triazole
	3-carboxylic acid ethyl
	ester
Compound 649	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	3-Mercapto-
	hydrobenzothiophene-	benzoyl chloride		1,2,4-triazole
	3-carboxylic acid ethyl
	ester
Compound 650	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	3-Mercapto-
	hydrobenzothiophene-	benzoyl chloride		1,2,4-triazole
	3-carboxylic acid ethyl
	ester
Compound 651	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	3-Mercapto-
	hydrobenzothiophene-	benzoyl chloride		1,2,4-triazole
	3-carboxylic acid ethyl
	ester
Compound 652	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	N,N-Diethyl
	hydrobenzothiophene-	benzoyl chloride		ethylenediamine
	3-carboxylic acid ethyl
	ester
Compound 653	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	p-Tolualdehyde	N,N-Diethyl
	hydrobenzothiophene-	benzoyl chloride		ethylenediamine
	3-carboxylic acid ethyl
	ester
Compound 654	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	N,N-Diethyl-
	hydrobenzothiophene-	benzoyl chloride		ethylenediamine
	3-carboxylic acid ethyl
	ester
Compound 655	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	N,N-Diethyl-
	hydrobenzothiophene-	benzoyl chloride		ethylenediamine
	3-carboxylic acid ethyl
	ester
Compound 656	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	N,N-Diethyl
	hydrobenzothiophene-	benzoyl chloride		ethylenediamine
	3-carboxylic acid ethyl
	ester
Compound 657	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	N,N-Diethyl-
	hydrobenzothiophene-	benzoyl chloride		ethylenediamine
	3-carboxylic acid ethyl
	ester
Compound 658	Ethyl 2-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	3-Mercapto-1-
	aminothiophene-3-	benzoyl chloride		propanol
	carboxylate
Compound 659	Ethyl 2-	3-(Chloromethyl)-	p-Tolualdehyde	3-Mercapto-1-
	aminothiophene-3-	benzoyl chloride		propanol
	carboxylate
Compound 660	Ethyl 2-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	3-Mercapto-1-
	aminothiophene-3-	benzoyl chloride		propanol
	carboxylate
Compound 661	Ethyl 2-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	3-Mercapto-1-
	aminothiophene-3-	benzoyl chloride		propanol
	carboxylate
Compound 662	Ethyl 2-	3-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	3-Mercapto-1-
	aminothiophene-3-	benzoyl chloride		propanol
	carboxylate
Compound 663	Ethyl 2-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	3-Mercapto-1-
	aminothiophene-3-	benzoyl chloride		propanol
	carboxylate
Compound 664	Ethyl 2-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	N,N-Diethyl-
	aminothiophene-3-	benzoyl chloride		N′-methyl-
	carboxylate			ethylenediamine
Compound 665	Ethyl 2-	3-(Chloromethyl)-	p-Tolualdehyde	N,N-Diethyl
	aminothiophene-3-	benzoyl chloride		N′-methyl-
	carboxylate			ethylenediamine
Compound 666	Ethyl 2-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	N,N-Diethyl-
	aminothiophene-3-	benzoyl chloride		N′-methyl-
	carboxylate			ethylenediamine
Compound 667	Ethyl 2-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	N,N-Diethyl-
	aminothiophene-3-	benzoyl chloride		N′-methyl-
	carboxylate			ethylenediamine
Compound 668	Ethyl 2-	3-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	N,N-Diethyl-
	aminothiophene-3-	benzoyl chloride		N′-methyl-
	carboxylate			ethylenediamine
Compound 669	Ethyl 2-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	N,N-Diethyl
	aminothiophene-3-	benzoyl chloride		N′-methyl-
	carboxylate			ethylenediamine
Compound 670	Ethyl 2-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	Diisopropanolamine
	aminothiophene-3-	benzoyl chloride
	carboxylate
Compound 671	Ethyl 2-	3-(Chloromethyl)-	p-Tolualdehyde	Diisopropanolamine
	aminothiophene-3-	benzoyl chloride
	carboxylate
Compound 672	Ethyl 2-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	Diisopropanolamine
	aminothiophene-3-	benzoyl chloride
	carboxylate
Compound 673	Ethyl 2-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	Diisopropanolamine
	aminothiophene-3-	benzoyl chloride
	carboxylate
Compound 674	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	N,N-Diethyl-
	hydrobenzothiophene-	benzoyl chloride		N′-methyl-
	3-carboxylic acid ethyl			ethylenediamine
	ester
Compound 675	2-Amino-4,5,6,7-tetra-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	N,N-Diethyl-
	hydrobenzothiophene-	benzoyl chloride		N′-methyl-
	3-carboxylic acid ethyl			ethylenediamine
	ester
Compound 676	Methyl 2-amino-5-	3-(Chloromethyl)-	p-Tolualdehyde	2-Mercapto-
	bromobenzoate	benzoyl chloride		ethanol
Compound 677	Methyl 2-amino-5-	3-(Chloromethyl)-	p-Tolualdehyde	2-Mercapto-
	bromobenzoate	benzoyl chloride		ethanol
Compound 678	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Chloro-3-	2-Mercapto-
	bromobenzoate	benzoyl chloride	trifluoromethylbenzaldehyde	ethanol
Compound 679	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Chloro-3-	2-Mercapto-
	bromobenzoate	benzoyl chloride	trifluoromethylbenzaldehyde	ethanol
Compound 680	Methyl 2-amino-5-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	Furfuryl
	chlorobenzoate	benzoyl chloride		mercaptan
Compound 681	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	Furfuryl
	chlorobenzoate	benzoyl chloride		mercaptan
Compound 682	Methyl 2-amino-5-	3-(Chloromethyl)-	p-Tolualdehyde	Furfuryl
	chlorobenzoate	benzoyl chloride		mercaptan
Compound 683	Methyl 2-amino-5-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	Furfuryl
	chlorobenzoate	benzoyl chloride		mercaptan
Compound 684	Methyl 2-amino-5-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	N,N′-
	chlorobenzoate	benzoyl chloride		Dimethyl-1,3-
				propane-
				diamine
Compound 685	Methyl 2-amino-5-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	N,N′-
	chlorobenzoate	benzoyl chloride		Dimethyl-1,3-
				propane-
				diamine
Compound 686	Methyl 2-amino-5-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	Furfuryl
	chlorobenzoate	benzoyl chloride		mercaptan
Compound 687	Methyl 2-amino-5-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	Furfuryl
	chlorobenzoate	benzoyl chloride		mercaptan
Compound 688	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	Furfuryl
	chlorobenzoate	benzoyl chloride		mercaptan
Compound 689	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	Furfuryl
	chlorobenzoate	benzoyl chloride		mercaptan
Compound 690	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	N,N′-
	chlorobenzoate	benzoyl chloride		Dimethyl-1,6-
				hexane-
				diamine
Compound 691	Methyl 2-amino-5-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	2-Mercapto-
	chlorobenzoate	benzoyl chloride		ethane-
				sulfonic acid
				sodium salt
Compound 692	Methyl 2-amino-5-	3-(Chloromethyl)-	m-Tolualdehyde	2-Mercapto-
	chlorobenzoate	benzoyl chloride		ethane-
				sulfonic acid
				sodium salt
Compound 693	Methyl 2-amino-5-	3-(Chloromethyl)-	p-Tolualdehyde	2-Mercapto-
	chlorobenzoate	benzoyl chloride		ethane-
				sulfonic acid
				sodium salt
Compound 694	Methyl 2-amino-5-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	2-Mercapto-
	chlorobenzoate	benzoyl chloride		ethane-
				sulfonic acid
				sodium salt
Compound 695	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	2-Mercapto-
	bromobenzoate	benzoyl chloride		ethanol
Compound 696	Methyl 2-amino-5-	3-(Chloromethyl)-	p-Tolualdehyde	2-Mercapto-
	bromobenzoate	benzoyl chloride		ethanol
Compound 697	Methyl 2-amino-5-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	2-Mercapto-
	bromobenzoate	benzoyl chloride		ethanol
Compound 698	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	2-Mercapto-
	bromobenzoate	benzoyl chloride		ethanol
Compound 699	Methyl 2-amino-5-	3-(Chloromethyl)-	m-Tolualdehyde	Furfuryl
	chlorobenzoate	benzoyl chloride		mercaptan
Compound 700	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Chloro-3-	Furfuryl
	chlorobenzoate	benzoyl chloride	trifluoromethylbenzaldehyde	mercaptan
Compound 701	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	N,N′-
	chlorobenzoate	benzoyl chloride		Dimethyl-1,3-
				propane-
				diamine
Compound 702	Methyl 2-amino-5-	3-(Chloromethyl)-	p-Tolualdehyde	N,N′-
	chlorobenzoate	benzoyl chloride		Dimethyl-1,3-
				propane-
				diamine
Compound 703	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Chloro-3-	2-Mercapto-
	chlorobenzoate	benzoyl chloride	trifluoromethylbenzaldehyde	ethane-
				sulfonic acid
				sodium salt
Compound 704	Methyl 2-amino-5-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	N,N′-
	chlorobenzoate	benzoyl chloride		Dimethyl-1,6-
				hexane-
				diamine
Compound 705	Methyl 2-amino-5-	3-(Chloromethyl)-	m-Tolualdehyde	N,N′-
	chlorobenzoate	benzoyl chloride		Dimethyl-1,6-
				hexane-
				diamine
Compound 706	Methyl 2-amino-5-	3-(Chloromethyl)-	p-Tolualdehyde	N,N′-
	chlorobenzoate	benzoyl chloride		Dimethyl-1,6-
				hexane-
				diamine
Compound 707	Methyl 3-amino-4-	3-(Chloromethyl)-	4-Chloro-3-	Diisopropanolamine
	methylthiophene-2-	benzoyl chloride	trifluoromethylbenzaldehyde
	carboxylate
Compound 708	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	2-Mercapto-
	chlorobenzoate	benzoyl chloride		ethane-
				sulfonic acid
				sodium salt
Compound 709	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Chloro-3-	2-Mercapto-
	chlorobenzoate	benzoyl chloride	trifluoromethylbenzaldehyde	ethane-
				sulfonic acid
				sodium salt
Compound 710	Methyl 3-amino-4-	3-(Chloromethyl)-	p-Tolualdehyde	N,N-Diethyl
	methylthiophene-2-	benzoyl chloride		N′-methyl-
	carboxylate			ethylenediamine
Compound 711	Methyl 3-amino-4-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	N,N-Diethyl-
	methylthiophene-2-	benzoyl chloride		N′-methyl-
	carboxylate			ethylenediamine
Compound 712	Methyl 3-amino-4-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	N,N-Diethyl-
	methylthiophene-2-	benzoyl chloride		N′-methyl-
	carboxylate			ethylenediamine
Compound 713	Methyl 2-amino-5-	4-(Chloromethyl)-	3-Fluorobenzaldehyde	4-(2-Aminoethyl)-
	bromobenzoate	benzoyl chloride		morpholine
Compound 714	Methyl 2-amino-5-	4-(Chloromethyl)-	4-Chloro-3-	4-(2-Aminoethyl)-
	bromobenzoate	benzoyl chloride	trifluoromethylbenzaldehyde	morpholine
Compound 715	Methyl 2-amino-5-	4-(Chloromethyl)-	p-Methoxybenzaldehyde	4-(2-Aminoethyl)-
	bromobenzoate	benzoyl chloride		morpholine
Compound 716	Methyl 2-amino-5-	4-(Chloromethyl)-	m-Methoxybenzaldehyde	4-(2-Aminoethyl)-
	bromobenzoate	benzoyl chloride		morpholine
Compound 717	Methyl 2-amino-5-	4-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	1-(4-Fluoro-
	bromobenzoate	benzoyl chloride		phenyl)-
				piperazine
Compound 718	Methyl 2-amino-5-	4-(Chloromethyl)-	m-Tolualdehyde	Diisopropanolamine
	bromobenzoate	benzoyl chloride
Compound 719	Methyl 2-amino-5-	4-(Chloromethyl)-	4-Fluorobenzaldehyde	Diisopropanolamine
	bromobenzoate	benzoyl chloride
Compound 720	Methyl 2-amino-5-	4-(Chloromethyl)-	3-Fluorobenzaldehyde	Diisopropanolamine
	bromobenzoate	benzoyl chloride
Compound 721	Methyl 2-amino-5-	4-(Chloromethyl)-	4-Chloro-3-	Diisopropanolamine
	bromobenzoate	benzoyl chloride	trifluoromethylbenzaldehyde
Compound 722	Methyl 2-amino-5-	4-(Chloromethyl)-	p-Methoxybenzaldehyde	Diisopropanolamine
	bromobenzoate	benzoyl chloride
Compound 723	Methyl 2-amino-5-	4-(Chloromethyl)-	m-Methoxybenzaldehyde	Diisopropanolamine
	bromobenzoate	benzoyl chloride
Compound 724	Methyl 2-amino-5-	4-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	Cineferin
	bromobenzoate	benzoyl chloride
Compound 725	Methyl 2-amino-5-	4-(Chloromethyl)-	3-Fluorobenzaldehyde	Cineferin
	bromobenzoate	benzoyl chloride
Compound 726	Methyl 2-amino-5-	4-(Chloromethyl)-	4-Chloro-3-	Cineferin
	bromobenzoate	benzoyl chloride	trifluoromethylbenzaldehyde
Compound 727	Methyl 2-amino-5-	4-(Chloromethyl)-	m-Methoxybenzaldehyde	Cineferin
	bromobenzoate	benzoyl chloride
Compound 728	Methyl 2-amino-5-	4-(Chloromethyl)-	p-Tolualdehyde	N-(2-(1-
	bromobenzoate	benzoyl chloride		Piperazino)
				acetyl)-
				morpholine
Compound 729	Methyl 2-amino-5-	4-(Chloromethyl)-	m-Tolualdehyde	N-(2-(1-
	bromobenzoate	benzoyl chloride		Piperazino)-
				acetyl)-
				morpholine
Compound 730	Methyl 2-amino-5-	4-(Chloromethyl)-	4-Fluorobenzaldehyde	N-(2-(1-
	bromobenzoate	benzoyl chloride		Piperazino)-
				acetyl)-
				morpholine
Compound 731	Methyl 2-amino-5-	4-(Chloromethyl)-	3-Fluorobenzaldehyde	N-(2-(1-
	bromobenzoate	benzoyl chloride		Piperazino)-
				acetyl)-
				morpholine
Compound 732	Methyl 2-amino-5-	4-(Chloromethyl)-	m-Methoxybenzaldehyde	N-(2-(1-
	bromobenzoate	benzoyl chloride		Piperazino)-
				acetyl)
				morpholine
Compound 733	Methyl 2-amino-5-	4-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	Bis(2-ethoxy-
	bromobenzoate	benzoyl chloride		ethyl)-amine
Compound 734	Methyl 2-amino-5-	4-(Chloromethyl)-	p-Tolualdehyde	Bis(2-ethoxy-
	bromobenzoate	benzoyl chloride		ethyl)-amine
Compound 735	Methyl 2-amino-5-	4-(Chloromethyl)-	m-Tolualdehyde	Bis(2-ethoxy-
	bromobenzoate	benzoyl chloride		ethyl)-amine
Compound 736	Methyl 2-amino-5-	4-(Chloromethyl)-	4-Fluorobenzaldehyde	Bis(2-ethoxy-
	bromobenzoate	benzoyl chloride		ethyl)amine
Compound 737	Methyl 2-amino-5-	4-(Chloromethyl)-	3-Fluorobenzaldehyde	Bis(2-ethoxy-
	bromobenzoate	benzoyl chloride		ethyl)amine
Compound 738	Methyl 2-amino-5-	4-(Chloromethyl)-	4-Chloro-3-	Bis(2-ethoxy-
	bromobenzoate	benzoyl chloride	trifluoromethylbenzaldehyde	ethyl)amine
Compound 739	Methyl 2-amino-5-	4-(Chloromethyl)-	p-Methoxybenzaldehyde	Bis(2-ethoxy-
	bromobenzoate	benzoyl chloride		ethyl)amine
Compound 740	Methyl 2-amino-5-	4-(Chloromethyl)-	m-Methoxybenzaldehyde	Bis(2-ethoxy-
	bromobenzoate	benzoyl chloride		ethyl)amine
Compound 741	Methyl 2-amino-5-	4-(Chloromethyl)-	p-Tolualdehyde ethanol	4-Piperidine-
	bromobenzoate	benzoyl chloride		ethanol
Compound 742	Methyl 2-amino-5-	4-(Chloromethyl)-	m-Tolualdehyde	4-Piperidine-
	bromobenzoate	benzoyl chloride		ethanol
Compound 743	Methyl 2-amino-5-	4-(Chloromethyl)-	4-Fluorobenzaldehyde	4-Piperidine-
	bromobenzoate	benzoyl chloride		ethanol
Compound 744	Methyl 2-amino-5-	4-(Chloromethyl)-	3-Fluorobenzaldehyde	4-Piperidine-
	bromobenzoate	benzoyl chloride		ethanol
Compound 745	Methyl 2-amino-5-	4-(Chloromethyl)-	4-Chloro-3-	4-Piperidine-
	bromobenzoate	benzoyl chloride	trifluoromethylbenzaldehyde	ethanol
Compound 746	Methyl 2-amino-5-	4-(Chloromethyl)-	m-Methoxybenzaldehyde	4-Piperidine-
	bromobenzoate	benzoyl chloride		ethanol
Compound 747	Methyl 2-amino-5-	4-(Chloromethyl)-	4-Chloro-3-	2-Morpholine-
	bromobenzoate	benzoyl chloride	trifluoromethylbenzaldehyde	4-yl-1-phenyl-
				ethylamine
Compound 748	Methyl 2-amino-5-	4-(Chloromethyl)-	p-Methoxybenzaldehyde	2-Morpholine-
	bromobenzoate	benzoyl chloride		4-yl-1-phenyl-
				ethylamine
Compound 749	Methyl 2-amino-5-	4-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	4-Amino-1,2-
	bromobenzoate	benzoyl chloride		diethyl-
				pyrazolidine
Compound 750	Methyl 2-amino-5-	4-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	4-Amino-1,2-
	bromobenzoate	benzoyl chloride		diethyl-
				pyrazolidine
Compound 751	Methyl 2-amino-5-	4-(Chloromethyl)-	3-Fluorobenzaldehyde	4-Amino-1,2-
	bromobenzoate	benzoyl chloride		diethyl-
				pyrazolidine
Compound 752	Methyl 2-amino-5-	4-(Chloromethyl)-	3-Fluorobenzaldehyde	4-Amino-1,2-
	bromobenzoate	benzoyl chloride		diethyl-
				pyrazolidine
Compound 753	Methyl 2-amino-5-	4-(Chloromethyl)-	4-Chloro-3-	4-Amino-1,2-
	bromobenzoate	benzoyl chloride	trifluoromethylbenzaldehyde	diethyl-
				pyrazolidine
Compound 754	Methyl 2-amino-5-	4-(Chloromethyl)-	4-Chloro-3-	4-Amino-1,2-
	bromobenzoate	benzoyl chloride	trifluoromethylbenzaldehyde	diethyl-
				pyrazolidine
Compound 755	Methyl 2-amino-5-	4-(Chloromethyl)-	p-Methoxybenzaldehyde	4-Amino-1,2-
	bromobenzoate	benzoyl chloride		diethyl-
				pyrazolidine
Compound 756	Methyl 2-amino-5-	4-(Chloromethyl)-	p-Methoxybenzaldehyde	4-Amino-1,2-
	bromobenzoate	benzoyl chloride		diethyl-
				pyrazolidine
Compound 757	Methyl 2-amino-5-	4-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	N-(3-Amino-
	bromobenzoate	benzoyl chloride		propyl)-N-
				methylaniline
Compound 758	Methyl 2-amino-5-	4-(Chloromethyl)-	p-Tolualdehyde	N-(3-Amino-
	bromobenzoate	benzoyl chloride		propyl)-N-
				methylaniline
Compound 759	Methyl 2-amino-5-	4-(Chloromethyl)-	4-Fluorobenzaldehyde	N-(3-Amino-
	bromobenzoate	benzoyl chloride		propyl)-N-
				methylaniline
Compound 760	Methyl 2-amino-5-	4-(Chloromethyl)-	3-Fluorobenzaldehyde	N-(3-Amino-
	bromobenzoate	benzoyl chloride		propyl)-N-
				methylaniline
Compound 761	Methyl 2-amino-5-	4-(Chloromethyl)-	4-Chloro-3-	N-(3-Amino-
	bromobenzoate	benzoyl chloride	trifluoromethylbenzaldehyde	propyl)-N-
				methylaniline
Compound 762	Methyl 2-amino-5-	4-(Chloromethyl)-	p-Methoxybenzaldehyde	N-(3-Amino-
	bromobenzoate	benzoyl chloride		propyl)-N-
				methylaniline
Compound 763	Methyl 2-amino-5-	4-(Chloromethyl)-	m-Methoxybenzaldehyde	N-(3-Amino-
	bromobenzoate	benzoyl chloride		propyl)-N-
				methylaniline
Compound 764	Methyl 2-amino-5-	4-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	2-(Ethylthio)-
	bromobenzoate	benzoyl chloride		ethylamine
Compound 765	Methyl 2-amino-5-	4-(Chloromethyl)-	p-Tolualdehyde	2-(Ethylthio)-
	bromobenzoate	benzoyl chloride		ethylamine
Compound 766	Methyl 2-amino-5-	4-(Chloromethyl)-	m-Tolualdehyde	2-(Ethylthio)-
	bromobenzoate	benzoyl chloride		ethylamine
Compound 767	Methyl 2-amino-5-	4-(Chloromethyl)-	4-Fluorobenzaldehyde	2-(Ethylthio)-
	bromobenzoate	benzoyl chloride		ethylamine
Compound 768	Methyl 2-amino-5-	4-(Chloromethyl)-	3-Fluorobenzaldehyde	2-(Ethylthio)-
	bromobenzoate	benzoyl chloride		ethylamine
Compound 769	Methyl 2-amino-5-	4-(Chloromethyl)-	4-Chloro-3-	2-(Ethylthio)-
	bromobenzoate	benzoyl chloride	trifluoromethylbenzaldehyde	ethylamine
Compound 770	Methyl 2-amino-5-	4-(Chloromethyl)-	p-Methoxybenzaldehyde	2-(Ethylthio)-
	bromobenzoate	benzoyl chloride		ethylamine
Compound 771	Methyl 2-amino-5-	4-(Chloromethyl)-	m-Methoxybenzaldehyde	2-(Ethylthio)-
	bromobenzoate	benzoyl chloride		ethylamine
Compound 772	Methyl 2-amino-5-	4-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	1-(2-Pyridyl)-
	bromobenzoate	benzoyl chloride		piperazine
Compound 773	Methyl 2-amino-5-	4-(Chloromethyl)-	pTolualdehyde	1-(2-Pyridyl)-
	bromobenzoate	benzoyl chloride		piperazine
Compound 774	Methyl 2-amino-5-	4-(Chloromethyl)-	4-Fluorobenzaldehyde	1-(2-Pyridyl)-
	bromobenzoate	benzoyl chloride		piperazine
Compound 775	Methyl 2-amino-5-	4-(Chloromethyl)-	3-Fluorobenzaldehyde	1-(2-Pyridyl)-
	bromobenzoate	benzoyl chloride		piperazine
Compound 776	Methyl 2-amino-5-	4-(Chloromethyl)-	4-Chloro-3-	1-(2-Pyridyl)-
	bromobenzoate	benzoyl chloride	trifluoromethylbenzaldehyde	piperazine
Compound 777	Methyl 2-amino-5-	4-(Chloromethyl)-	p-Methoxybenzaldehyde	1-(2-Pyridyl)-
	bromobenzoate	benzoyl chloride		piperazine
Compound 778	Methyl 2-amino-5-	4-(Chloromethyl)-	m-Methoxybenzaldehyde	1-(2-Pyridyl)-
	bromobenzoate	benzoyl chloride		piperazine
Compound 779	Ethyl 2-	3-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	Diisopropanolamine
	aminothiophene-3-	benzoyl chloride
	carboxylate
Compound 780	Ethyl 2-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	Diisopropanolamine
	aminothiophene-3-	benzoyl chloride
	carboxylate
Compound 781	Methyl 2-amino-4-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	2-Mercapto-
	methylthiophene-3-	benzoyl chloride		ethane-
	carboxylate			sulfonic acid
Compound 782	Methyl 2-amino-4-	3-(Chloromethyl)-	p-Tolualdehyde	2-Mercapto-
	methylthiophene-3-	benzoyl chloride		ethane-
	carboxylate			sulfonic acid
Compound 783	Methyl 2-amino-4-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	2-Mercapto-
	methylthiophene-3-	benzoyl chloride		ethane-
	carboxylate			sulfonic acid
Compound 784	Methyl 2-amino-4-	3-(Chloromethyl)-	4-Chloro-3-	2-Mercapto-
	methylthiophene-3-	benzoyl chloride	trifluoromethylbenzaldehyde	ethane-
	carboxylate			sulfonic acid
Compound 785	Methyl 2-amino-4-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	2-Mercapto-
	methylthiophene-3-	benzoyl chloride		ethane-
	carboxylate			sulfonic acid
Compound 786	Methyl 2-amino-4-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	Diethanolamine
	methylthiophene-3-	benzoyl chloride
	carboxylate
Compound 787	Methyl 2-amino-4-	3-(Chloromethyl)-	p-Tolualdehyde	Diethanolamine
	methylthiophene-3-	benzoyl chloride
	carboxylate
Compound 788	Methyl 2-amino-4-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	Diethanolamine
	methylthiophene-3-	benzoyl chloride
	carboxylate
Compound 789	Methyl 2-amino-4-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	Diethanolamine
	methylthiophene-3-	benzoyl chloride
	carboxylate
Compound 790	Methyl 2-amino-4-	3-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	Diethanolamine
	methylthiophene-3-	benzoyl chloride
	carboxylate
Compound 791	Methyl 2-amino-4-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	Diethanolamine
	methylthiophene-3-	benzoyl chloride
	carboxylate
Compound 792	Ethyl-2-amino-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	Diisopropanolamine
	benzo(B)thiophene-	benzoyl chloride
	3-carboxylate
Compound 793	Ethyl-2-amino-	3-(Chloromethyl)-	p-Tolualdehyde	Diisopropanolamine
	benzo(B)thiophene-	benzoyl chloride
	3-carboxylate
Compound 794	Ethyl-2-amino-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	Diisopropanolamine
	benzo(B)thiophene-	benzoyl chloride
	3-carboxylate
Compound 795	Ethyl-2-amino-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	Diisopropanolamine
	benzo(B)thiophene-	benzoyl chloride
	3-carboxylate
Compound 796	Ethyl-2-amino-	3-(Chloromethyl)-	4-Chloro-3-	Diisopropanolamine
	benzo(B)thiophene-	benzoyl chloride	trifluoromethylbenzaldehyde
	3-carboxylate
Compound 797	Ethyl-2-amino-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	Diisopropanolamine
	benzo(B)thiophene-	benzoyl chloride
	3-carboxylate
Compound 798	Ethyl-2-amino-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	4-Piperidine-
	benzo(B)thiophene-	benzoyl chloride		methanol
	3-carboxylate
Compound 799	Ethyl-2-amino-	3-(Chloromethyl)-	p-Tolualdehyde	4-Piperidine-
	benzo(B)thiophene-	benzoyl chloride		methanol
	3-carboxylate
Compound 800	Ethyl-2-amino-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	4-Piperidine-
	benzo(B)thiophene-	benzoyl chloride		methanol
	3-carboxylate
Compound 801	Ethyl-2-amino-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	4-Piperidine-
	benzo(B)thiophene-	benzoyl chloride		methanol
	3-carboxylate
Compound 802	Ethyl-2-amino-	3-(Chloromethyl)-	4-Chloro-3-	4-Piperidine-
	benzo(B)thiophene-	benzoyl chloride	trifluoromethylbenzaldehyde	methanol
	3-carboxylate
Compound 803	Ethyl-2-amino-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	4-Piperidine-
	benzo(B)thiophene-	benzoyl chloride		methanol
	3-carboxylate
Compound 804	Ethyl-2-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	Diisopropanolamine
	aminocyclopenta(B)-	benzoyl chloride
	thiophene-3-
	carboxylate
Compound 805	Ethyl-2-	3-(Chloromethyl)-	p-Tolualdehyde	Diisopropanolamine
	aminocyclopenta(B)-	benzoyl chloride
	thiophene-3-
	carboxylate
Compound 806	Ethyl-2-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	Diisopropanolamine
	aminocyclopenta(B)-	benzoyl chloride
	thiophene-3-
	carboxylate
Compound 807	Ethyl-2-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	Diisopropanolamine
	aminocyclopenta(B)-	benzoyl chloride
	thiophene-3-
	carboxylate
Compound 808	Ethyl-2-	3-(Chloromethyl)-	4-Chloro-3-	Diisopropanolamine
	aminocyclopenta(B)-	benzoyl chloride	trifluoromethylbenzaldehyde
	thiophene-3-
	carboxylate
Compound 809	Ethyl-2-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	Diisopropanolamine
	aminocyclopenta(B)-	benzoyl chloride
	thiophene-3-
	carboxylate
Compound 810	Ethyl-2-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	N,N-Diethyl-
	aminocyclopenta(B)-	benzoyl chloride		ethylenediamine
	thiophene-3-
	carboxylate
Compound 811	Ethyl-2-	3-(Chloromethyl)-	p-Tolualdenhyde	N,N-Diethyl-
	aminocyclopenta(B)-	benzoyl chloride		ethylenediamine
	thiophene-3-
	carboxylate
Compound 812	Ethyl-2-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	N,N-Diethyl-
	aminocyclopenta(B)-	benzoyl chloride		ethylenediamine
	thiophene-3-
	carboxylate
Compound 813	Ethyl-2-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	N,N-Diethyl-
	aminocyclopenta(B)-	benzoyl chloride		ethylenediamine
	thiophene-3-
	carboxylate
Compound 814	Ethyl-2-	3-(Chloromethyl)-	4-Chloro-3-	N,N-Diethyl-
	aminocyclopenta(B)-	benzoyl chloride	trifluoromethylbenzaldehyde	ethylenediamine
	thiophene-3-
	carboxylate
Compound 815	Ethyl-2-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	N,N-Diethyl-
	aminocyclopenta(B)-	benzoyl chloride		ethylenediamine
	thiophene-3-
	carboxylate
Compound 816	Ethyl-2-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	4-Piperidine-
	aminocyclopenta(B)-	benzoyl chloride		methanol
	thiophene-3-
	carboxylate
Compound 817	Ethyl-2-	3-(Chloromethyl)-	p-Tolualdehyde	4-Piperidine-
	aminocyclopenta(B)-	benzoyl chloride		methanol
	thiophene-3-
	carboxylate
Compound 818	Ethyl-2-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	4-Piperidine-
	aminocyclopenta(B)-	benzoyl chloride		methanol
	thiophene-3-
	carboxylate
Compound 819	Ethyl-2-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	4-Piperidine-
	aminocyclopenta(B)-	benzoyl chloride		methanol
	thiophene-3-
	carboxylate
Compound 820	Ethyl-2-	3-(Chloromethyl)-	4-Chloro-3-	4-Piperidine-
	aminocyclopenta(B)-	benzoyl chloride	trifluoromethylbenzaldehyde	methanol
	thiophene-3-
	carboxylate
Compound 821	Ethyl-2-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	4-Piperidine-
	aminocyclopenta(B)-	benzoyl chloride		methanol
	thiophene-3-
	carboxylate
Compound 822	Methyl 2-amino-4-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	Dimethylamine
	methylthiophene-3-	benzoyl chloride		hydrochloride
	carboxylate
Compound 823	Methyl 2-amino-4-	3-(Chloromethyl)-	p-Tolualdehyde	Dimethylamine
	methylthiophene-3-	benzoyl chloride		hydrochloride
	carboxylate
Compound 824	Methyl 2-amino-4-	3-(Chloromethyl)-	4-Chloro-3-	Dimethylamine
	methylthiophene-3-	benzoyl chloride	trifluoromethylbenzaldehyde	hydrochloride
	carboxylate
Compound 825	Methyl 2-amino-4-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	Dimethylamine
	methylthiophene-3-	benzoyl chloride		hydrochloride
	carboxylate
Compound 826	Methyl 2-amino-4-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	1-(2-
	methylthiophene-3-	benzoyl chloride		Pyrimidyl)-
	carboxylate			piperazine
Compound 827	Methyl 2-amino-4-	3-(Chloromethyl)-	p-Tolualdehyde	1-(2-
	methylthiophene-3-	benzoyl chloride		Pyrimidyl)-
	carboxylate			piperazine
Compound 828	Methyl 2-amino-4-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	1-(2-
	methylthiophene-3-	benzoyl chloride		Pyrimidyl)-
	carboxylate			piperazine
Compound 829	Methyl 2-amino-4-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	1-(2-
	methylthiophene-3-	benzoyl chloride		Pyrimidyl)-
	carboxylate			piperazine
Compound 830	Methyl 2-amino-4-	3-(Chloromethyl)-	4-Chloro-3-	1-(2-
	methylthiophene-3-	benzoyl chloride	trifluoromethylbenzaldehyde	Pyrimidyl)-
	carboxylate			piperazine
Compound 831	Methyl 2-amino-4-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	1-(2-
	methylthiophene-3-	benzoyl chloride		Pyrimidyl)-
	carboxylate			piperazine
Compound 832	Methyl 2-amino-4-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	1,4-Dioxa-8-
	methylthiophene-3-	benzoyl chloride		azaspiro[4,5]
	carboxylate			decane
Compound 833	Methyl 2-amino-4-	3-(Chloromethyl)-	p-Tolualdehyde	1,4-Dioxa-8-
	methylthiophene-3-	benzoyl chloride		azaspiro[4,5]
	carboxylate			decane
Compound 834	Methyl 2-amino-4-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	1,4-Dioxa-8-
	methylthiophene-3-	benzoyl chloride		azaspiro[4,5]
	carboxylate			decane
Compound 835	Methyl 2-amino-4-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	1,4-Dioxa-8-
	methylthiophene-3-	benzoyl chloride		azaspiro[4,5]
	carboxylate			decane
Compound 836	Methyl 2-amino-4-	3-(Chloromethyl)-	4-Chloro-3-	1,4-Dioxa-8-
	methylthiophene-3-	benzoyl chloride	trifluoromethylbenzaldehyde	azaspiro[4,5]
	carboxylate			decane
Compound 837	Methyl 2-amino-4-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	1,4-Dioxa-8-
	methylthiophene-3-	benzoyl chloride		azaspiro[4,5]
	carboxylate			decane
Compound 838	Methyl 2-amino-4-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	1,1,7,7-
	methylthiophene-3-	benzoyl chloride		Tetraethyldiethylenetriamine
	carboxylate
Compound 839	Methyl 2-amino-4-	3-(Chloromethyl)-	p-Tolualdehyde	1,1,7,7-
	methylthiophene-3	benzoyl chloride		Tetraethyldiethylenetriamine
	carboxylate
Compound 840	Methyl 2-amino-4-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	1,1,7,7-
	methylthiophene-3-	benzoyl chloride		Tetraethyldiethylenetriamine
	carboxylate
Compound 841	Methyl 2-amino-4-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	1,1,7,7-
	methylthiophene-3-	benzoyl chloride		Tetraethyldiethylenetriamine
	carboxylate
Compound 842	Methyl 2-amino-4-	3-(Chloromethyl)-	4-Chloro-3-	1,1,7,7-
	methylthiophene-3-	benzoyl chloride	trifluoromethylbenzaldehyde	Tetraethyldiethylenetriamine
	carboxylate
Compound 843	Methyl 2-amino-4-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	1,1,7,7-
	methylthiophene-3-	benzoyl chloride		Tetraethyldiethylenetriamine
	carboxylate
Compound 844	Ethyl 2-amino-4,5-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	Diisopropanolamine
	dimethylthiophene-	benzoyl chloride
	3-carboxylate
Compound 845	Ethyl 2-amino-4,5-	3-(Chloromethyl)-	p-Tolualdehyde	Diisopropanolamine
	dimethylthiophene-	benzoyl chloride
	3-carboxylate
Compound 846	Ethyl 2-amino-4,5-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	Diisopropanolamine
	dimethylthiophene-	benzoyl chloride
	3-carboxylate
Compound 847	Ethyl 2-amino-4,5-	3-(Chloromethyl)-	4-Chloro-3-	Diisopropanolamine
	dimethylthiophene-	benzoyl chloride	trifluoromethylbenzaldehyde
	3-carboxylate
Compound 848	Ethyl 2-amino-4,5-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	Diisopropanolamine
	dimethylthiophene-	benzoyl chloride
	3-carboxylate
Compound 849	Ethyl 2-amino-	3-(Chloromethyl)-	4-Chloro-3	1,1,7,7-
	4,5,6,7-tetrahydrobenzo	benzoyl chloride	trifluoromethylbenzaldehyde	Tetraethyldiethylenetriamine
	(B)thiophene-
	3-carboxylate
Compound 850	Ethyl 2-amino-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	1,1,7,7-
	4,5,6,7-tetrahydrobenzo	benzoyl chloride		Tetraethyldiethylenetriamine
	(B)thiophene-
	3-carboxylate
Compound 851	Methyl 2-amino-4-	3-(Chloromethyl)-	4-Chloro-3-	Diisopropanolamine
	methylthiophene-3-	benzoyl chloride	trifluoromethylbenzaldehyde
	carboxylate
Compound 852	Methyl 2-amino-4-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	Diisopropanolamine
	methylthiophene-3-	benzoyl chloride
	carboxylate
Compound 853	2-Amino-5-	3-(Chloromethyl)-	4-Chloro-3-	Diisopropanolamine
	fluorobenzoic acid	benzoyl chloride	trifluoromethylbenzaldehyde
	methyl ester
Compound 854	2-Amino-5-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	Diisopropanolamine
	fluorobenzoic acid	benzoyl chloride
	methyl ester
Compound 855	Ethyl 2-amino-	3-(Chloromethyl)-	4-Chloro-3-	1,1,7,7-
	4,5,6,7-tetrahydrobenzo	benzoyl chloride	trifluoromethylbenzaldehyde	Tetraethyldiethylenetriamine
	(B)thiophene-
	3-carboxylate
Compound 856	Ethyl 2-amino-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	1,1,7,7-
	4,5,6,7-tetrahydrobenzo	benzoyl chloride		Tetraethyldiethylenetriamine
	(B)thiophene-
	3-carboxylate
Compound 857	2-Amino-5-	3-(Chloromethyl)-	4-Chloro-3-	Diisopropanolamine
	fluorobenzoic acid	benzoyl chloride	trifluoromethylbenzaldehyde
	methyl ester
Compound 858	2-Amino-5-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	N,N-Diethyl-
	piperidine-1-yl-	benzoyl chloride		N′-methyl-
	benzoic acid methyl			ethylenediamine
	ester
Compound 859	2-Amino-5-	3-(Chloromethyl)-	p-Tolualdehyde	N,N-Diethyl-
	piperidine-1-yl-	benzoyl chloride		N′-methyl-
	benzoic acid methyl			ethylenediamine
	ester
Compound 860	2-Amino-5-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	N,N-Diethyl-
	piperidine-1-yl-	benzoyl chloride		N′-methyl-
	benzoic acid methyl			ethylenediamine
	ester
Compound 861	2-Amino-5-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	N,N-Diethyl-
	piperidine-1-yl-	benzoyl chloride		N′-methyl-
	benzoic acid methyl			ethylenediamine
	ester
Compound 862	2-Amino-5-	3-(Chloromethyl)-	4-Chloro-3-	N,N-Diethyl-
	piperidine-1-yl-	benzoyl chloride	trifluoromethylbenzaldehyde	N′-methyl-
	benzoic acid methyl			ethylenediamine
	ester
Compound 863	2-Amino-5-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	N,N-Diethyl-
	piperidine-1-yl-	benzoyl chloride		N′-methyl-
	benzoic acid methyl			ethylenediamine
	ester
Compound 864	2-Amino-5-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	4-Piperazine-
	piperidine-1-yl-	benzoyl chloride		ethanol
	benzoic acid methyl
	ester
Compound 865	2-Amino-5-	3-(Chloromethyl)-	p-Tolualdehyde	4-Piperazine-
	piperidine-1-yl-	benzoyl chloride		ethanol
	benzoic acid methyl
	ester
Compound 866	2-Amino-5-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	4-Piperazine-
	piperidine-1-yl-	benzoyl chloride		ethanol
	benzoic acid methyl
	ester
Compound 867	2-Amino-5-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	4-Piperazine-
	piperidine-1-yl-	benzoyl chloride		ethanol
	benzoic acid methyl
	ester
Compound 868	2-Amino-5-	3-(Chloromethyl)-	4-Chloro-3-	4-Piperazine-
	piperidine-1-yl-	benzoyl chloride	trifluoromethylbenzaldehyde	ethanol
	benzoic acid methyl
	ester
Compound 869	2-Amino-5-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	4-Piperazine-
	piperidine-1-yl-	benzoyl chloride		ethanol
	benzoic acid methyl
	ester
Compound 870	2-Amino-5-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	4-Hydroxypiperidine
	piperidine-1-yl-	benzoyl chloride
	benzoic acid methyl
	ester
Compound 871	2-Amino-5-	3-(Chloromethyl)-	p-Tolualdehyde	4-Hydroxypiperidine
	piperidine-1-yl-	benzoyl chloride
	benzoic acid methyl
	ester
Compound 872	2-Amino-5-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	4-Hydroxypiperidine
	piperidine-1-yl-	benzoyl chloride
	benzoic acid methyl
	ester
Compound 873	2-Amino-5-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	4-Hydroxypiperidine
	piperidine-1-yl-	benzoyl chloride
	benzoic acid methyl
	ester
Compound 874	2-Amino-5-	3-(Chloromethyl)-	4-Chloro-3-	4-Hydroxypiperidine
	piperidine-1-yl-	benzoyl chloride	trifluoromethylbenzaldehyde
	benzoic acid methyl
	ester
Compound 875	2-Amino-5-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	4-Hydroxypiperidine
	piperidine-1-yl-	benzoyl chloride
	benzoic acid methyl
	ester
Compound 876	2-Amino-5-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	2-(Diethylamino)-
	piperidine-1-yl-	benzoyl chloride		ethanethiol
	benzoic acid methyl
	ester
Compound 877	2-Amino-5-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	2-(Diethylamino)-
	piperidine-1-yl-	benzoyl chloride		ethanethiol
	benzoic acid methyl
	ester
Compound 878	2-Amino-5-	3-(Chloromethyl)-	4-Chloro-3-	2-(Diethylamino)-
	piperidine-1-yl-	benzoyl chloride	trifluoromethylbenzaldehyde	ethanethiol
	benzoic acid methyl
	ester
Compound 879	2-Amino-5-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	2-(Diethylamino)-
	piperidine-1-yl-	benzoyl chloride		ethanethiol
	benzoic acid methyl
	ester
Compound 880	2-Amino-5-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	2-Mercapto-
	piperidine-1-yl-	benzoyl chloride		ethanol
	benzoic acid methyl
	ester
Compound 881	2-Amino-5-	3-(Chloromethyl)-	p-Tolualdehyde	2-Mercapto-
	piperidine-1-yl-	benzoyl chloride		ethanol
	benzoic acid methyl
	ester
Compound 882	2-Amino-5-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	2-Mercapto-
	piperidine-1-yl-	benzoyl chloride		ethanol
	benzoic acid methyl
	ester
Compound 883	2-Amino-5-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	2-Mercapto-
	piperidine-1-yl-	benzoyl chloride		ethanol
	benzoic acid methyl
	ester
Compound 884	2-Amino-5-	3-(Chloromethyl)-	4-Chloro-3-	2-Mercapto-
	piperidine-1-yl-	benzoyl chloride	trifluoromethylbenzaldehyde	ethanol
	benzoic acid methyl
	ester
Compound 885	2-Amino-5-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	2-Mercapto-
	piperidine-1-yl-	benzoyl chloride		ethanol
	benzoic acid methyl
	ester
Compound 886	2-Amino-5-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	3-Mercapto-
	piperidine-1-yl-	benzoyl chloride		propionic acid
	benzoic acid methyl
	ester
Compound 887	2-Amino-5-	3-(Chloromethyl)-	p-Tolualdehyde	3-Mercapto-
	piperidine-1-yl-	benzoyl chloride		propionic acid
	benzoic acid methyl
	ester
Compound 888	2-Amino-5-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	3-Mercapto-
	piperidine-1-yl-	benzoyl chloride		propionic acid
	benzoic acid methyl
	ester
Compound 889	2-Amino-5-	3-(Chloromethyl)-	4-Chloro-3-	3-Mercapto-
	piperidine-1-yl-	benzoyl chloride	trifluoromethylbenzaldehyde	propionic acid
	benzoic acid methyl
	ester
Compound 890	2-Amino-5-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	3-Mercapto-
	piperidine-1-yl-	benzoyl chloride		propionic acid
	benzoic acid methyl
	ester
Compound 891	2-Amino-5-	3-(Chloromethyl)-	4-Chloro-3-	Mercapto-
	piperidine-1-yl-	benzoyl chloride	trifluoromethylbenzaldehyde	acetic acid
	benzoic acid methyl
	ester
Compound 892	2-Amino-5-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	Mercapto-
	piperidine-1-yl-	benzoyl chloride		acetic acid
	benzoic acid methyl
	ester
Compound 893	2-Amino-5-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	1,2,3,4-Tetra-
	piperidine-1-yl-	benzoyl chloride		hydropyrido-
	benzoic acid methyl			[4,3-b][1,8]-
	ester			naphthyridine
Compound 894	2-Amino-5-	3-(Chloromethyl)-	p-Tolualdehyde	1,2,3,4-Tetra-
	piperidine-1-yl-	benzoyl chloride		hydropyrido-
	benzoic acid methyl			[4,3-b][1,8]-
	ester			naphthyridine
Compound 895	2-Amino-5-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	1,2,3,4-Tetra-
	piperidine-1-yl-	benzoyl chloride		hydropyrido-
	benzoic acid methyl			[4,3-b][1,8]-
	ester			naphthyridine
Compound 896	2-Amino-5-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	1,2,3,4-Tetra-
	piperidine-1-yl-	benzoyl chloride		hydropyrido-
	benzoic acid methyl			[4,3-b][1,8]-
	ester			naphthyridine
Compound 897	2-Amino-5-	3-(Chloromethyl)-	4-Chloro-3-	1,2,3,4-Tetra-
	piperidine-1-yl-	benzoyl chloride	trifluoromethylbenzaldehyde	hydropyrido-
	benzoic acid methyl			[4,3-b][1,8]-
	ester			naphthyridine
Compound 898	2-Amino-5-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	1,2,3,4-Tetra-
	piperidine-1-yl-	benzoyl chloride		hydropyrido-
	benzoic acid methyl			[4,3-b][1,8]-
	ester			naphthyridine
Compound 899	2-Amino-5-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	3-Mercapto-
	piperidine-1-yl-	benzoyl chloride		1,2-propane-
	benzoic acid methyl			diol
	ester
Compound 900	2-Amino-5-	3-(Chloromethyl)-	p-Tolualdehyde	3-Mercapto-
	piperidine-1-yl-	benzoyl chloride		1,2-propane-
	benzoic acid methyl			diol
	ester
Compound 901	2-Amino-5-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	3-Mercapto-
	piperidine-1-yl-	benzoyl chloride		1,2-propane-
	benzoic acid methyl			diol
	ester
Compound 902	2-Amino-5-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	3-Mercapto-
	piperidine-1-yl-	benzoyl chloride		1,2-propane-
	benzoic acid methyl			diol
	ester
Compound 903	2-Amino-5-	3-(Chloromethyl)-	4-Chloro-3-	3-Mercapto-
	piperidine-1-yl-	benzoyl chloride	trifluoromethylbenzaldehyde	1,2-propane-
	benzoic acid methyl			diol
	ester
Compound 904	2-Amino-5-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	3-Mercapto-
	piperidine-1-yl-	benzoyl chloride		1,2-propane-
	benzoic acid methyl			diol
	ester
Compound 905	2-Amino-5-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	1,1,7,7-
	piperidine-1-yl-	benzoyl chloride		Tetraethyl-
	benzoic acid methyl			diethylene-
	ester			triamine
Compound 906	2-Amino-5-	3-(Chloromethyl)-	p-Tolualdehyde	1,1,7,7-
	piperidine-1-yl-	benzoyl chloride		Tetraethyl-
	benzoic acid methyl			diethylene-
	ester			triamine
Compound 907	2-Amino-5-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	1,1,7,7-
	piperidine-1-yl-	benzoyl chloride		Tetraethyl-
	benzoic acid methyl			diethylene-
	ester			triamine
Compound 908	2-Amino-5-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	1,1,7,7-
	piperidine-1-yl-	benzoyl chloride		Tetraethyl-
	benzoic acid methyl			diethylene-
	ester			triamine
Compound 909	2-Amino-5-	3-(Chloromethyl)-	4-Chloro-3-	1,1,7,7-
	piperidine-1-yl-	benzoyl chloride	trifluoromethylbenzaldehyde	Tetraethyl-
	benzoic acid methyl			diethylene-
	ester			triamine
Compound 910	2-Amino-5-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	1,1,7,7-
	piperidine-1-yl-	benzoyl chloride		Tetraethyl-
	benzoic acid methyl			diethylene-
	ester			triamine
Compound 911	2-Amino-5-	3-(Chloromethyl)-	4-Chloro-3-	N,N-Diethyl-
	dipropylamino-	benzoyl chloride	trifluoromethylbenzaldehyde	N′-methyl-
	benzoic acid methyl			ethylenediamine
	ester
Compound 912	2-Amino-5-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	N,N-Diethyl-
	dipropylamino-	benzoyl chloride		N′-methyl-
	benzoic acid methyl			ethylenediamine
	ester
Compound 913	2-Amino-5-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	N,N-bis(2-
	piperidine-1-yl-	benzoyl chloride		hydroxyethyl)-
	benzoic acid methyl			ethylenediamine
	ester
Compound 914	2-Amino-5-	3-(Chloromethyl)-	4-Chloro-3-	N,N-bis(2-
	piperidine-1-yl-	benzoyl chloride	trifluoromethylbenzaldehyde	hydroxyethyl)-
	benzoic acid methyl			ethylenediamine
	ester
Compound 915	2-Amino-5-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	N,N-bis(2-
	piperidine-1-yl-	benzoyl chloride		hydroxyethyl)-
	benzoic acid methyl			ethylenediamine
	ester
Compound 916	2-Amino-5-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	N,N-Diethyl-
	pyrrolidine-1-yl-	benzoyl chloride		N′-methyl-
	benzoic acid methyl			ethylenediamine
	ester
Compound 917	2-Amino-5-	3-(Chloromethyl)-	4-Chloro-3-	N,N-Diethyl-
	pyrrolidine-1-yl-	benzoyl chloride	trifluoromethylbenzaldehyde	N′-methyl-
	benzoic acid methyl			ethylenediamine
	ester
Compound 918	2-Amino-5-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	N,N-Diethyl-
	pyrrolidine-1-yl-	benzoyl chloride		N′-methyl-
	benzoic acid methyl			ethylenediamine
	ester
Compound 919	2-Amino-5-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	2-Mercapto-
	pyrrolidine-1-yl-	benzoyl chloride		ethanol
	benzoic acid methyl
	ester
Compound 920	2-Amino-5-	3-(Chloromethyl)-	4-Chloro-3-	2-Mercapto-
	pyrrolidine-1-yl-	benzoyl chloride	trifluoromethylbenzaldehyde	ethanol
	benzoic acid methyl
	ester
Compound 921	2-Amino-5-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	2-Mercapto-
	pyrrolidine-1-yl-	benzoyl chloride		ethanol
	benzoic acid methyl
	ester
Compound 922	2-Amino-5-(4-	3-(Chloromethyl)-	4-Chloro-3-	N,N-Diethyl-
	methyl-	benzoyl chloride	trifluoromethylbenzaldehyde	N′-methyl-
	[1,4]diazepin-1-yl)-			ethylenediamine
	benzoic acid methyl
	ester
Compound 923	2-Amino-5-[4-(2-	3-(Chloromethyl)-	4-Chloro-3-	2-Mercapto-
	hydroxy-ethyl)-	benzoyl chloride	trifluoromethylbenzaldehyde	ethanol
	piperazine-1-yl]-
	benzoic acid methyl
	ester
Compound 924	2-Amino-5-[4-(2-	3-(Chloromethyl)-	4-Chloro-3-	N,N-Diethyl-
	hydroxy-ethyl)-	benzoyl chloride	trifluoromethylbenzaldehyde	N′-methyl-
	piperazine-1-yl]-			ethylenediamine
	benzoic acid methyl
	ester
Compound 925	1-(4-Amino-3-	3-(Chloromethyl)-	4-Chloro-3-	2-Mercapto-
	methoxycarbonylphenyl)-	benzoyl chloride	trifluoromethylbenzaldehyde	ethanol
	piperidine-
	3-carboxylic acid
Compound 926	2-Amino-5-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	2-Mercapto-
	thiomorpholine-4-yl-	benzoyl chloride		ethanol
	benzoic acid methyl
	ester
Compound 927	2-Amino-5-	3-(Chloromethyl)-	4-Chloro-3-	2-Mercapto-
	thiomorpholine-4-yl-	benzoyl chloride	trifluoromethylbenzaldehyde	ethanol
	benzoic acid methyl
	ester
Compound 928	2-Amino-5-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	2-Mercapto-
	thiomorpholine-4-yl-	benzoyl chloride		ethanol
	benzoic acid methyl
	ester
Compound 929	2-Amino-5-	3-(Chloromethyl)-	4-Chloro-3-	N,N-Diethyl-
	thiomorpholine-4-yl-	benzoyl chloride	trifluoromethylbenzaldehyde	N′-methyl-
	benzoic acid methyl			ethylenediamine
	ester
Compound 930	Methyl 2-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	Dimethyl-
	aminothiophene-3-	benzoyl chloride		amine
	carboxylate			hydrochloride
Compound 931	2-Amino-5-(4-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	N,N-Diethyl-
	methyl-	benzoyl chloride		N′-methyl-
	[1,4]diazepin-1-yl)-			ethylenediamine
	benzoic acid methyl
	ester
Compound 932	2-Amino-5-(4-	3-(Chloromethyl)-	4-Chloro-3-	2-Mercapto-
	methyl-	benzoyl chloride	trifluoromethylbenzaldehyde	ethanol
	[1,4]diazepin-1-yl)-
	benzoic acid methyl
	ester
Compound 933	2-Amino-5-(4-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	N,N-Diethyl-
	methyl-	benzoyl chloride		N′-methyl-
	[1,4]diazepin-1-yl)-			ethylenediamine
	benzoic acid methyl
	ester
Compound 934	1-(4-Amino-3-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	2-Mercapto-
	methoxycarbonylphenyl)-	benzoyl chloride		ethanol
	piperidine-
	3-carboxylic acid
Compound 935	2-Amino-5-	3,4-Dimethoxybenzoyl	3,4-Dimethylbenzaldehyde
	piperidine-1-yl-	chloride
	benzoic acid ethyl
	ester
Compound 936	2-Amino-5-	3,4-Dimethoxybenzoyl	Nicotinaldehyde
	piperidine-1-yl-	chloride
	benzoic acid ethyl
	ester
Compound 937	2-Amino-5-	3,4-Dimethoxybenzoyl	Imidazole-2-
	piperidine-1-yl-	chloride	carboxaldehyde
	benzoic acid ethyl
	ester
Compound 938	2-Amino-5-	3,4-Dimethoxybenzoyl	Vanillin
	piperidine-1-yl-	chloride
	benzoic acid ethyl
	ester
Compound 939	2-Amino-5-	3,4-Dimethoxybenzoyl	3,4-Dimethylbenzaldehyde
	morpholine-4-yl-	chloride
	benzoic acid ethyl
	ester
Compound 940	2-Amino-5-	3,4-Dimethoxybenzoyl	Vanillin
	morpholine-4-yl-	chloride
	benzoic acid ethyl
	ester
Compound 941	2-Amino-5-	3,4-Dimethoxybenzoyl	p-Methoxybenzaldehyde
	morpholine-4-yl-	chloride
	benzoic acid ethyl
	ester
Compound 942	2-Amino-5-	3-(Chloromethyl)-	4-Chloro-3-	Diisopropanolamine
	piperidine-1-yl-	benzoyl chloride	trifluoromethylbenzaldehyde
	benzoic acid ethyl
	ester
Compound 943	2-Amino-5-hydroxy-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	Diisopropanolamine
	benzoic acid methyl	benzoyl chloride
	ester
Compound 944	2-Amino-5-(2-oxo-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	Diisopropanolamine
	pyrrolidine-1-yl)-	benzoyl chloride
	benzoic acid methyl
	ester
Compound 945	2-Amino-5-(2-oxo-	3-(Chloromethyl)-	4-Chloro-3-	Diisopropanolamine
	pyrrolidine-1-yl)-	benzoyl chloride	trifluoromethylbenzaldehyde
	benzoic acid methyl
	ester
Compound 946	2-Amino-5-(2-oxo-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	Diisopropanolamine
	pyrrolidine-1-yl)-	benzoyl chloride
	benzoic acid methyl
	ester
Compound 947	2-Amino-5-(2-oxo-	3-(Chloromethyl)-	4-Fluorobenzaldehyde	Diisopropanolamine
	pyrrolidine-1-yl)-	benzoyl chloride
	benzoic acid methyl
	ester
Compound 948	2-Amino-5-(2-oxo-	3-(Chloromethyl)-	p-Tolualdehyde	Diisopropanolamine
	pyrrolidine-1-yl)-	benzoyl chloride
	benzoic acid methyl
	ester
Compound 949	2-Amino-5-hydroxy-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	Diisopropanolamine
	benzoic acid methyl	benzoyl chloride
	ester
Compound 950	2-Amino-5-hydroxy-	3-(Chloromethyl)-	4-Chloro-3-	Diisopropanolamine
	benzoic acid methyl	benzoyl chloride	trifluoromethylbenzaldehyde
	ester
Compound 951	2-Amino-5-hydroxy-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	Diisopropanolamine
	benzoic acid methyl	benzoyl chloride
	ester
Compound 952	2-Amino-5-hydroxy-	3-(Chloromethyl)-	4-Chloro-3-	Diisopropanolamine
	benzoic acid methyl	benzoyl chloride	trifluoromethylbenzaldehyde
	ester
Compound 953	2-Amino-5-hydroxy-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	Diisopropanolamine
	benzoic acid methyl	benzoyl chloride
	ester
Compound 954	2-Amino-5-hydroxy-	3-(Chloromethyl)-	4-Chloro-3-	Diisopropanolamine
	benzoic acid methyl	benzoyl chloride	trifluoromethylbenzaldehyde
	ester
Compound 955	Methyl 2-	3,4-Dimethoxybenzoyl	4-Chloro-3-
	aminothiophene-3-	chloride	trifluoromethylbenzaldehyde
	carboxylate
Compound 956	Ethyl 2-amino-4-	3-(Chloromethyl)-	4-Chloro-3-	Diethylamine
	methylthiophene-3-	benzoyl chloride	trifluoromethylbenzaldehyde
	carboxylate
Compound 957	Ethyl 2-amino-4-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	Diethylamine
	methylthiophene-3-	benzoyl chloride
	carboxylate
Compound 958	2-Amino-5-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	Diisopropanolamine
	piperidine-1-yl-	benzoyl chloride
	benzoic acid ethyl
	ester
Compound 959	3-Amino-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	Diisopropanolamine
	naphthalene-2-	benzoyl chloride
	carboxylic acid
	methyl ester
Compound 960	3-Amino-	3-(Chloromethyl)-	p-Tolualdehyde	Diisopropanolamine
	naphthalene-2-	benzoyl chloride
	carboxylic acid
	methyl ester
Compound 961	3-Amino-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	Diisopropanolamine
	naphthalene-2-	benzoyl chloride
	carboxylic acid
	methyl ester
Compound 962	3-Amino-	3-(Chloromethyl)-	4-Chloro-3-	Diisopropanolamine
	naphthalene-2-	benzoyl chloride	trifluoromethylbenzaldehyde
	carboxylic acid
	methyl ester
Compound 963	3-Amino-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	Diisopropanolamine
	naphthalene-2-	benzoyl chloride
	carboxylic acid
	methyl ester
Compound 964	2-Amino-nicotinoic	3-(Chloromethyl)-	3-Fluorobenzaldehyde	Diisopropanolamine
	acid methyl ester	benzoyl chloride
Compound 965	2-Amino-nicotinoic	3-(Chloromethyl)-	p-Tolualdehyde	Diisopropanolamine
	acid methyl ester	benzoyl chloride
Compound 966	2-Amino-nicotinoic	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	Diisopropanolamine
	acid methyl ester	benzoyl chloride
Compound 967	2-Amino-nicotinoic	3-(Chloromethyl)-	4-Chloro-3-	Diisopropanolamine
	acid methyl ester	benzoyl chloride	trifluoromethylbenzaldehyde
Compound 968	2-Amino-nicotinoic	3-(Chloromethyl)-	p-Methoxybenzaldehyde	Diisopropanolamine
	acid methyl ester	benzoyl chloride
Compound 969	3-Amino-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	1-(2-Hydroxyethyl)-
	naphthalene-2-	benzoyl chloride		piperazine
	carboxylic acid
	methyl ester
Compound 970	3-Amino-	3-(Chloromethyl)-	p-Tolualdehyde	1-(2-Hydroxyethyl)-
	naphthalene-2-	benzoyl chloride		piperazine
	carboxylic acid
	methyl ester
Compound 971	3-Amino-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	1-(2-Hydroxyethyl)-
	naphthalene-2-	benzoyl chloride		piperazine
	carboxylic acid
	methyl ester
Compound 972	3-Amino-	3-(Chloromethyl)-	4-Chloro-3-	1-(2-Hydroxyethyl)-
	naphthalene-2-	benzoyl chloride	trifluoromethylbenzaldehyde	piperazine
	carboxylic acid
	methyl ester
Compound 973	3-Amino-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	1-(2-Hydroxyethyl)-
	naphthalene-2-	benzoyl chloride		piperazine
	carboxylic acid
	methyl ester
Compound 974	4-Amino-thiophene-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	Diisopropanolamine
	3-carboxylic acid	benzoyl chloride
	methyl ester
Compound 975	4-Amino-thiophene-	3-(Chloromethyl)-	m-Tolualdehyde	Diisopropanolamine
	3-carboxylic acid	benzoyl chloride
	methyl ester
Compound 976	4-Amino-thiophene-	3-(Chloromethyl)-	p-Tolualdehyde	Diisopropanolamine
	3-carboxylic acid	benzoyl chloride
	methyl ester
Compound 977	4-Amino-thiophene-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	Diisopropanolamine
	3-carboxylic acid	benzoyl chloride
	methyl ester
Compound 978	4-Amino-thiophene-	3-(Chloromethyl)-	4-Chloro-3-	Diisopropanolamine
	3-carboxylic acid	benzoyl chloride	trifluoromethylbenzaldehyde
	methyl ester
Compound 979	4-Amino-thiophene-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	Diisopropanolamine
	3-carboxylic acid	benzoyl chloride
	methyl ester
Compound 980	4-Amino-thiophene-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	1-(2-Hydroxyethyl)-
	3-carboxylic acid	benzoyl chloride		piperazine
	methyl ester
Compound 981	4-Amino-thiophene-	3-(Chloromethyl)-	p-Tolualdehyde	1-(2-Hydroxyethyl)-
	3-carboxylic acid	benzoyl chloride		piperazine
	methyl ester
Compound 982	4-Amino-thiophene-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	1-(2-Hydroxyethyl)-
	3-carboxylic acid	benzoyl chloride		piperazine
	methyl ester
Compound 983	4-Amino-thiophene-	3-(Chloromethyl)-	4-Chloro-3-	1-(2-Hydroxyethyl)-
	3-carboxylic acid	benzoyl chloride	trifluoromethylbenzaldehyde	piperazine
	methyl ester
Compound 984	4-Amino-thiophene-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	1-(2-Hydroxyethyl)-
	3-carboxylic acid	benzoyl chloride		piperazine
	methyl ester
Compound 985	2-Amino-5-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	Diisopropanolamine
	fluorobenzoic acid	benzoyl chloride
	methyl ester
Compound 986	2-Amino-5-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	Diisopropanolamine
	fluorobenzoic acid	benzoyl chloride
	methyl ester
Compound 987	2-Amino-5-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	Diisopropanolamine
	fluorobenzoic acid	benzoyl chloride
	methyl ester
Compound 988	2-Amino-5-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	Diisopropanolamine
	fluorobenzoic acid	benzoyl chloride
	methyl ester
Compound 989	2-Amino-5-	3-(Chloromethyl)-	p-Tolualdehyde	Diisopropanolamine
	fluorobenzoic acid	benzoyl chloride
	methyl ester
Compound 990	2-Amino-5-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	Diisopropanolamine
	fluorobenzoic acid	benzoyl chloride
	methyl ester
Compound 991	3-Amino-5-tert-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	1-(2-Hydroxyethyl)-
	butyl-thiophene-2-	benzoyl chloride		piperazine
	carboxylic acid
	methyl ester
Compound 992	3-Amino-thiophene-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	Diisopropanolamine
	2-carboxylic acid	benzoyl chloride
	methyl ester
Compound 993	3-Amino-thiophene-	3-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	Diisopropanolamine
	2-carboxylic acid	benzoyl chloride
	methyl ester
Compound 995	3-Amino-thiophene-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	Diethylamine
	2-carboxylic acid	benzoyl chloride
	methyl ester
Compound 996	Methyl 2-amino-5-	3-(Chloromethyl)-	3-Fluoroacetophenone	Diisopropanolamine
	bromobenzoate	benzoyl chloride
Compound 997	Methyl 2-amino-5-	3-(Chloromethyl)-	p-Methoxy	Diisopropanolamine
	bromobenzoate	benzoyl chloride	acetophenone
Compound 998	Methyl 2-amino-5-	3-(Chloromethyl)-	4-(3-Dimethyl-	Diisopropanolamine
	chlorobenzoate	benzoyl chloride	amino-propoxy)-
			benzaldehyde
Compound 999	Methyl 2-amino-5-	3-(Chloromethyl)-	4-(3-Dimethyl-	N,N-Diethyl-
	chlorobenzoate	benzoyl chloride	amino-propoxy)-	N′-methylethylenediamine
			benzaldehyde
Compound 1000	Methyl 2-amino-5-	3-(Chloromethyl)-	(4-Formyl-	N,N-Diethyl-
	chlorobenzoate	benzoyl chloride	phenoxy)-acetic	N′-methylethylenediamine
			acid
Compound 1001	2-Amino-4,5,6,7-	3-(Chloromethyl)-	4-Trifluoromethoxybenzaldehyde	N,N-Diethyl-
	tetrahydro-	benzoyl chloride		N′-methylethylenediamine
	benzothiophene-3-
	carboxylic acid
Compound 1002	2-Amino-4,5,6,7-	3-(Chloromethyl)-	4-(2-Hydroxy-	N,N-Diethyl-
	tetrahydro-	benzoyl chloride	ethoxy)-	N′-methylethylenediamine
	benzothiophene-3-		benzaldehyde
	carboxylic acid
Compound 1003	2-Amino-4,5,6,7-	3-(Chloromethyl)-	3-Fluoro-	N,N-Diethyl-
	tetrahydro-	benzoyl chloride	acetophenone	N′-methylethylenediamine
	benzothiophene-3-
	carboxylic acid
Compound 1004	Methyl 2-amino-5-	Quinoxaline-2-	3-Fluorobenzaldehyde
	chlorobenzoate	carbonyl chloride
Compound 1005	Methyl 2-amino-5-	Quinoxaline-2-	3,4-Dimethylbenzaldehyde
	chlorobenzoate	carbonyl chloride
Compound 1006	Methyl 2-amino-5-	Quinoxaline-2-	4-Chloro-3-
	chlorobenzoate	carbonyl chloride	trifluoromethylbenzaldehyde
Compound 1007	Methyl 2-amino-5-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	3-Mercapto-
	chlorobenzoate	benzoyl chloride		propane-1,2-
				diol
Compound 1008	Methyl 2-amino-5-	3-(Chloromethyl)-	p-Tolualdehyde	3-Mercapto-
	chlorobenzoate	benzoyl chloride		propane-1,2-
				diol
Compound 1009	Methyl 2-amino-5-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	3-Mercapto-
	chlorobenzoate	benzoyl chloride		propane-1,2-
				diol
Compound 1010	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Chloro-3-	3-Mercapto-
	chlorobenzoate	benzoyl chloride	trifluoromethylbenzaldehyde	propane-1,2-
				diol
Compound 1011	Methyl 2-amino-5-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	3-Mercapto-
	chlorobenzoate	benzoyl chloride		propane-1,2-
				diol
Compound 1012	Methyl 2-amino-5-	3-(Chloromethyl)-	4-Trifluoromethoxybenzaldehyde	3-Mercapto-
	chlorobenzoate	benzoyl chloride		propane-1,2-
				diol
Compound 1013	2-Amino-4,5-bis-(2-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	3-Mercapto-
	methoxy-ethoxy)-	benzoyl chloride		propane-1,2-
	benzoic acid ethyl			diol
	ester
Compound 1014	2-Amino-4,5-bis-(2-	3-(Chloromethyl)-	p-Tolualdehyde	3-Mercapto-
	methoxy-ethoxy)-	benzoyl chloride		propane-1,2-
	benzoic acid ethyl			diol
	ester
Compound 1015	2-Amino-4,5-bis-(2-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	3-Mercapto-
	methoxy-ethoxy)-	benzoyl chloride		propane-1,2-
	benzoic acid ethyl			diol
	ester
Compound 1016	2-Amino-4,5-bis-(2-	3-(Chloromethyl)-	4-Chloro-3-	3-Mercapto-
	methoxy-ethoxy)-	benzoyl chloride	trifluoromethylbenzaldehyde	propane-1,2-
	benzoic acid ethyl			diol
	ester
Compound 1017	2-Amino-5-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	3-Mercapto-
	methoxy-benzoic	benzoyl chloride		propane-1,2-
	acid methyl ester			diol
Compound 1018	2-Amino-5-	3-(Chloromethyl)-	p-Tolualdehyde	3-Mercapto-
	methoxy-benzoic	benzoyl chloride		propane-1,2-
	acid methyl ester			diol
Compound 1019	2-Amino-5-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	3-Mercapto-
	methoxy-benzoic	benzoyl chloride		propane-1,2-
	acid methyl ester			diol
Compound 1020	2-Amino-5-	3-(Chloromethyl)-	4-Chloro-3-	3-Mercapto-
	methoxy-benzoic	benzoyl chloride	trifluoromethylbenzaldehyde	propane-1,2-
	acid methyl ester			diol
Compound 1021	2-Amino-5-	3-(Chloromethyl)-	p-Methoxybenzaldehyde-	3-Mercapto-
	methoxy-benzoic	benzoyl chloride		propane-1,2-
	acid methyl ester			diol
Compound 1022	2-Amino-5-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	N,N-Diethyl-
	methoxy-benzoic	benzoyl chloride		N′-methylethylenediamine
	acid methyl ester
Compound 1023	2-Amino-5-	3-(Chloromethyl)-	4-Chloro-3-	N,N-Diethyl-
	methoxy-benzoic	benzoyl chloride	trifluoromethylbenzaldehyde	N′-methylethylenediamine
	acid methyl ester
Compound 1024	2-Amino-5-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	N,N-Diethyl-
	methoxy-benzoic	benzoyl chloride		N′-methylethylenediamine
	acid methyl ester
Compound 1025	2-Amino-5-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	N,N-Diethyl-
	methoxy-ethoxy-	benzoyl chloride		N′-methylethylenediamine
	benzoic acid methyl
	ester
Compound 1026	2-Amino-5-	3-(Chloromethyl)-	p-Tolualdehyde	N,N-Diethyl-
	methoxy-ethoxy-	benzoyl chloride		N′-methyl-
	benzoic acid methyl			ethylenediamine
	ester
Compound 1027	2-Amino-5-	3-(Chloromethyl)-	4-Chloro-3-	N,N-Diethyl-
	methoxy-ethoxy-	benzoyl chloride	trifluoromethylbenzaldehyde	N′-methyl-
	benzoic acid methyl			ethylenediamine
	ester
Compound 1028	2-Amino-4,5-bis-(2-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	N,N-Diethyl-
	methoxy-ethoxy)-	benzoyl chloride		N′-methyl-
	benzoic acid ethyl			ethylenediamine
	ester
Compound 1029	2-Amino-4,5-bis-(2-	3-(Chloromethyl)-	p-Tolualdehyde	N,N-Diethyl-
	methoxy-ethoxy)-	benzoyl chloride		N′-methyl-
	benzoic acid ethyl			ethylenediamine
	ester
Compound 1030	2-Amino-4,5-bis-(2-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	N,N-Diethyl-
	methoxy-ethoxy)-	benzoyl chloride		N′-methyl-
	benzoic acid ethyl			ethylenediamine
	ester
Compound 1031	2-Amino-4,5-bis-(2-	3-(Chloromethyl)-	4-Chloro-3-	N,N-Diethyl-
	methoxy-ethoxy)-	benzoyl chloride	trifluoromethylbenzaldehyde	N′-methyl-
	benzoic acid ethyl			ethylenediamine
	ester
Compound 1032	2-Amino-4,5-bis-(2-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	N,N-Diethyl-
	methoxy-ethoxy)-	benzoyl chloride		N′-methyl-
	benzoic acid ethyl			ethylenediamine
	ester
Compound 1033	2-Amino-5-[2-(2-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	N,N-Diethyl-
	methoxy-ethoxy)-	benzoyl chloride		N′-methyl-
	ethoxy]-benzoic			ethylenediamine
	acid methyl ester
Compound 1034	2-Amino-5-[2-(2-	3-(Chloromethyl)-	p-Tolualdehyde	N,N-Diethyl-
	methoxy-ethoxy)-	benzoyl chloride		N′-methyl-
	ethoxy]-benzoic			ethylenediamine
	acid methyl ester
Compound 1035	2-Amino-5-[2-(2-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	N,N-Diethyl-
	methoxy-ethoxy)-	benzoyl chloride		N′-methyl-
	ethoxy]-benzoic			ethylenediamine
	acid methyl ester
Compound 1036	2-Amino-5-[2-(2-	3-(Chloromethyl)-	4-Chloro-3-trifluoromethylbenzaldehyde	N,N-Diethyl-
	methoxy-ethoxy)-	benzoyl chloride		N′-methyl-
	ethoxy]-benzoic			ethylenediamine
	acid methyl ester
Compound 1037	2-Amino-5-[2-(2-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	N,N-Diethyl-
	methoxy-ethoxy)-	benzoyl chloride		N′-methyl-
	ethoxy]-benzoic			ethylenediamine
	acid methyl ester
Compound 1038	2-Amino-5-(3-	3-(Chloromethyl)-	4-Chloro-3-	N,N-Diethyl-
	piperidine-1-yl-	benzoyl chloride	trifluoromethylbenzaldehyde	N′-methyl-
	propoxy)-benzoic			ethylenediamine
	acid methyl ester
Compound 1039	2-Amino-5-(3-	3-(Chloromethyl)-	4-Chloro-3-	2-Mercapto-
	piperidine-1-yl-	benzoyl chloride	trifluoromethylbenzaldehyde	ethanol
	propoxy)-benzoic
	acid methyl ester
Compound 1040	2-Amino-5-(3-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	2-Mercapto-
	piperidine-1-yl-	benzoyl chloride		ethanol
	propoxy)-benzoic
	acid methyl ester
Compound 1041	2-Amino-5-(3-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	2-Mercapto-
	piperidine-1-yl-	benzoyl chloride		ethanol
	propoxy)-benzoic
	acid methyl ester
Compound 1042	2-Amino-5-(2-	3-(Chloromethyl)-	p-Tolualdehyde	2-Mercapto-
	piperidine-1-yl-	benzoyl chloride		ethanol
	ethoxy)-benzoic
	acid methyl ester
Compound 1043	2-Amino-5-(2-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	2-Mercapto-
	piperidine-1-yl-	benzoyl chloride		ethanol
	ethoxy)-benzoic
	acid methyl ester
Compound 1044	2-Amino-5-(2-	3-(Chloromethyl)-	4-Chloro-3-	2-Mercapto-
	piperidine-1-yl-	benzoyl chloride	trifluoromethylbenzaldehyde	ethanol
	ethoxy)-benzoic
	acid methyl ester
Compound 1045	2-Amino-5-(2-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	2-Mercapto-
	piperidine-1-yl-	benzoyl chloride		ethanol
	ethoxy)-benzoic
	acid methyl ester
Compound 1046	2-Amino-5-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	N,N-Diethyl-
	cyclohexylmethoxy-	benzoyl chloride		N′-methyl-
	benzoic acid methyl			ethylenediamine
	ester
Compound 1047	2-Amino-5-	3-(Chloromethyl)-	p-Tolualdehyde	N,N-Diethyl-
	cyclohexylmethoxy-	benzoyl chloride		N′-methyl-
	benzoic acid methyl			ethylenediamine
	ester
Compound 1048	2-Amino-5-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	N,N-Diethyl-
	cyclohexylmethoxy-	benzoyl chloride		N′-methyl-
	benzoic acid methyl			ethylenediamine
	ester
Compound 1049	2-Amino-5-	3-(Chloromethyl)-	4-Chloro-3-	N,N-Diethyl-
	cyclohexylmethoxy-	benzoyl chloride	trifluoromethylbenzaldehyde	N′-methyl-
	benzoic acid methyl			ethylenediamine
	ester
Compound 1050	2-Amino-5-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	N,N-Diethyl-
	cyclohexylmethoxy-	benzoyl chloride		N′-methyl-
	benzoic acid methyl			ethylenediamine
	ester
Compound 1051	2-Amino-5-(4-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	2-Mercapto-
	fluoro-butoxy)-	benzoyl chloride		ethanol
	benzoic acid methyl
	ester
Compound 1052	2-Amino-5-(4-	3-(Chloromethyl)-	p-Tolualdehyde	2-Mercapto-
	fluoro-butoxy)-	benzoyl chloride		ethanol
	benzoic acid methyl
	ester
Compound 1053	2-Amino-5-(4-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	2-Mercapto-
	fluoro-butoxy)-	benzoyl chloride		ethanol
	benzoic acid methyl
	ester
Compound 1054	2-Amino-5-(4-	3-(Chloromethyl)-	4-Chloro-3-	2-Mercapto-
	fluoro-butoxy)-	benzoyl chloride	trifluoromethylbenzaldehyde	ethanol
	benzoic acid methyl
	ester
Compound 1055	2-Amino-5-(4-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	2-Mercapto-
	fluoro-butoxy)-	benzoyl chloride		ethanol
	benzoic acid methyl
	ester
Compound 1056	Ethyl 2-amino-	3-(Chloromethyl)-	p-Tolualdehyde	1,1,7,7-
	4,5,6,7-	benzoyl chloride		Tetraethyl-
	tetrahydrobenzo(B)-			diethylene-
	thiophene-3-			triamine
	carboxylate
Compound 1057	2-Amino-5-(4-	3-(Chloromethyl)-	3-Fluorobenzaldehyde	N,N-Diethyl-
	fluoro-butoxy)-	benzoyl chloride		N′-methyl-
	benzoic acid methyl			ethylenediamine
	ester
Compound 1058	2-Amino-5-(4-	3-(Chloromethyl)-	p-Tolualdehyde	N,N-Diethyl-
	fluoro-butoxy)-	benzoyl chloride		N′-methyl-
	benzoic acid methyl			ethylenediamine
	ester
Compound 1059	2-Amino-5-(4-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	N,N-Diethyl-
	fluoro-butoxy)-	benzoyl chloride		N′-methyl-
	benzoic acid methyl			ethylenediamine
	ester
Compound 1060	2-Amino-5-(4-	3-(Chloromethyl)-	4-Chloro-3-	N,N-Diethyl-
	fluoro-butoxy)-	benzoyl chloride	trifluoromethylbenzaldehyde	N′-methyl-
	benzoic acid methyl			ethylenediamine
	ester
Compound 1061	2-Amino-5-(4-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	N,N-Diethyl-
	fluoro-butoxy)-	benzoyl chloride		N′-methyl-
	benzoic acid methyl			ethylenediamine
	ester
Compound 1062	2-Amino-5-(4-	3-(Chloromethyl)-	3-Trifluoro-	2-Mercapto-
	Hydroxypiperidine-	benzoyl chloride	methyl-4-chlorobenzaldehyde	ethanol
	1-yl)-benzoic acid
	methyl ester
Compound 1063	2-Amino-5-(4-	3-(Chloromethyl)-	3-Trifluoro-	2-Mercapto-
	hydroxymethyl-	benzoyl chloride	methyl-4-chlorobenzaldehyde	ethanol
	piperidine-1-yl)-
	benzoic acid methyl
	ester
Compound 1064	2-Amino-5-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	2-Mercapto-
	morpholine-4-yl-	benzoyl chloride		ethanol
	benzoic acid methyl
	ester
Compound 1065	2-Amino-5-	3-(Chloromethyl)-	3-Trifluoro-	2-Mercapto-
	morpholine-4-yl-	benzoyl chloride	methyl-4-chlorobenzaldehyde	ethanol
	benzoic acid methyl
	ester
Compound 1066	2-Amino-5-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	2-Mercapto-
	morpholine-4-yl-	benzoyl chloride		ethanol
	benzoic acid methyl
	ester
Compound 1067	2-Amino-5-	3-(Chloromethyl)-	3-Trifluoro-	2-Mercapto-
	[1,4′]bipiperidinyl-1′-	benzoyl chloride	methyl-4-chlorobenzaldehyde	ethanol
	yl-benzoic acid
	methyl ester
Compound 1068	2-Amino-5-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	2-Mercapto-
	[1,4′]bipiperidinyl-1′-	benzoyl chloride		ethanol
	yl-benzoic acid
	methyl ester
Compound 1069	2-Amino-5-(4-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	2-Mercapto-
	methyl-piperidine-1-	benzoyl chloride		ethanol
	yl)-benzoic acid
	methyl ester
Compound 1070	2-Amino-5-(4-	3-(Chloromethyl)-	3-Trifluoro-	2-Mercapto-
	methyl-piperidine-1-	benzoyl chloride	methyl-4-chlorobenzaldehyde	ethanol
	yl)-benzoic acid
	methyl ester
Compound 1071	2-Amino-5-(4-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	2-Mercapto-
	methyl-piperidine-1-	benzoyl chloride		ethanol
	yl)-benzoic acid
	methyl ester
Compound 1072	2-Amino-5-(4-	3-(Chloromethyl)-	3-Trifluoro-	2-Mercapto-
	methyl-piperazine-	benzoyl chloride	methyl-4-chlorobenzaldehyde	ethanol
	1-yl)-benzoic acid
	methyl ester
Compound 1073	2-Amino-5-(4-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	2-Mercapto-
	methyl-piperazine-	benzoyl chloride		ethanol
	1-yl)-benzoic acid
	methyl ester
Compound 1074	2-Amino-5-	3-(Chloromethyl)-	3,4-Dimethylbenzaldehyde	N,N-Diethyl-
	morpholine-4-yl-	benzoyl chloride		N′-methyl-
	benzoic acid methyl			ethylenediamine
	ester
Compound 1075	2-Amino-5-	3-(Chloromethyl)-	3-Trifluoro-	N,N-Diethyl-
	morpholine-4-yl-	benzoyl chloride	methyl-4-chlorobenzaldehyde	N′-methyl-
	benzoic acid methyl			ethylenediamine
	ester
Compound 1076	2-Amino-5-	3-(Chloromethyl)-	p-Methoxybenzaldehyde	N,N-Diethyl-
	morpholine-4-yl-	benzoyl chloride		N′-methyl-
	benzoic acid methyl			ethylenediamine
	ester

Starting compounds and reaction paths used in the synthesis of compounds corresponding to compounds A in synthesizing compounds 853, 854, 857 to 929, 931 to 942, 944 to 948, 958 to 973, 985 to 990, 1013 to 1055, and 1057 to 1076 are shown in Table 2. In the table, compounds A, D, and E correspond to compounds described in Examples and schemes A to H.

	TABLE 2
	A′	D	E	Reaction path
Compound 853	2-Amino-5-			Scheme G
	fluorobenzoic acid
Compound 854	2-Amino-5-			Scheme G
	fluorobenzoic acid
Compound 857	2-Amino-5-			Scheme G
	fluorobenzoic acid
Compound 858	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 859	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 860	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 861	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 862	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 863	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 864	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 865	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 866	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 867	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 868	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 869	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 870	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 871	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 872	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 873	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 874	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 875	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 876	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 877	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 878	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 879	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 880	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 881	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 882	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 883	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 884	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 885	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 886	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 887	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 888	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 889	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 890	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 891	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 892	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 893	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 894	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 895	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 896	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 897	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 898	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 899	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 900	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 901	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 902	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 903	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 904	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 905	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 906	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 907	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 908	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 909	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 910	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 911	5-Amino-2-nitro-	Propionaldehyde		Scheme H
	benzoic acid
	methyl ester
Compound 912	5-Amino-2-nitro-	Propionaldehyde		Scheme H
	benzoic acid
	methyl ester
Compound 913	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 914	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 915	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 916	5-Chloro-2-nitro-	Pyrrolidine		Scheme A
	benzoic acid
Compound 917	5-Chloro-2-nitro-	Pyrrolidine		Scheme A
	benzoic acid
Compound 918	5-Chloro-2-nitro-	Pyrrolidine		Scheme A
	benzoic acid
Compound 919	5-Chloro-2-nitro-	Pyrrolidine		Scheme A
	benzoic acid
Compound 920	5-Chloro-2-nitro-	Pyrrolidine		Scheme A
	benzoic acid
Compound 921	5-Chloro-2-nitro-	Pyrrolidine		Scheme A
	benzoic acid
Compound 922	5-Chloro-2-nitro-	1-Methyl-		Scheme A
	benzoic acid	homopiperazine
Compound 923	5-Chloro-2-nitro-	1-Piperazineethanol		Scheme A
	benzoic acid
Compound 924	5-Chloro-2-nitro-	1-Piperazineethanol		Scheme A
	benzoic acid
Compound 925	5-Chloro-2-nitro-	3-Piperidine-		Scheme A
	benzoic acid	carboxylic acid
Compound 926	5-Chloro-2-nitro-	Thiomorpholine		Scheme A
	benzoic acid
Compound 927	5-Chloro-2-nitro-	Thiomorpholine		Scheme A
	benzoic acid
Compound 928	5-Chloro-2-nitro-	Thiomorpholine		Scheme A
	benzoic acid
Compound 929	5-Chloro-2-nitro-	Thiomorpholine		Scheme A
	benzoic acid
Compound 931	5-Chloro-2-nitro-	1-Methyl-		Scheme A
	benzoic acid	homopiperazine
Compound 932	5-Chloro-2-nitro-	1-Methyl-		Scheme A
	benzoic acid	homopiperazine
Compound 933	5-Chloro-2-nitro-	1-Methyl-		Scheme A
	benzoic acid	homopiperazine
Compound 934	5-Chloro-2-nitro-	3-Piperidine-		Scheme A
	benzoic acid	carboxylic acid
Compound 935	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 936	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 937	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 938	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 939	5-Chloro-2-nitro-	Morpholine		Scheme A
	benzoic acid
Compound 940	5-Chloro-2-nitro-	Morpholine		Scheme A
	benzoic acid
Compound 941	5-Chloro-2-nitro-	Morpholine		Scheme A
	benzoic acid
Compound 942	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 944	5-Amino-2-nitro-	4-Chloro-butyryl		Scheme D
	benzoic acid	chloride
Compound 945	5-Amino-2-nitro-	4-Chloro-butyryl		Scheme D
	benzoic acid	chloride
Compound 946	5-Amino-2-nitro-	4-Chloro-butyryl		Scheme D
	benzoic acid	chloride
Compound 947	5-Amino-2-nitro-	4-Chloro-butyryl		Scheme D
	benzoic acid	chloride
Compound 948	5-Amino-2-nitro-	4-Chloro-butyryl		Scheme D
	benzoic acid	chloride
Compound 958	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 959	3-Amino-			Scheme G
	naphthalene-2-
	carboxylic acid
Compound 960	3-Amino-			Scheme G
	naphthalene-2-
	carboxylic acid
Compound 961	3-Amino-			Scheme G
	naphthalene-2-
	carboxylic acid
Compound 962	3-Amino-			Scheme G
	naphthalene-2-
	carboxylic acid
Compound 963	3-Amino-			Scheme G
	naphthalene-2-
	carboxylic acid
Compound 964	2-Amino-nicotinoic			Scheme G
	acid
Compound 965	2-Amino-nicotinoic			Scheme G
	acid
Compound 966	2-Amino-nicotinoic			Scheme G
	acid
Compound 967	2-Amino-nicotinoic			Scheme G
	acid
Compound 968	2-Amino-nicotinoic			Scheme G
	acid
Compound 969	3-Amino-			Scheme G
	naphthalene-2-
	carboxylic acid
Compound 970	3-Amino-			Scheme G
	naphthalene-2-
	carboxylic acid
Compound 971	3-Amino-			Scheme G
	naphthalene-2-
	carboxylic acid
Compound 972	3-Amino-			Scheme G
	naphthalene-2-
	carboxylic acid
Compound 973	3-Amino-			Scheme G
	naphthalene-2-
	carboxylic acid
Compound 985	2-Amino-5-fluorobenzoic			Scheme G
	acid
Compound 986	2-Amino-5-fluorobenzoic			Scheme G
	acid
Compound 987	2-Amino-5-fluorobenzoic			Scheme G
	acid
Compound 988	2-Amino-5-fluorobenzoic			Scheme G
	acid
Compound 989	2-Amino-5-fluorobenzoic			Scheme G
	acid
Compound 990	2-Amino-5-fluorobenzoic			Scheme G
	acid
Compound 1013	3,4-Dihydroxy-	1-Bromo-2-		Scheme F
	benzoic acid ethyl	methoxy-ethane
	ester
Compound 1014	3,4-Dihydroxy-	1-Bromo-2-		Scheme F
	benzoic acid ethyl	methoxy-ethane
	ester
Compound 1015	3,4-Dihydroxy-	1-Bromo-2-		Scheme F
	benzoic acid ethyl	methoxy-ethane
	ester
Compound 1016	3,4-Dihydroxy-	1-Bromo-2-		Scheme F
	benzoic acid ethyl	methoxy-ethane
	ester
Compound 1017	5-Methoxy-2-nitro-			Scheme E
	benzoic acid
Compound 1018	5-Methoxy-2-nitro-			Scheme E
	benzoic acid
Compound 1019	5-Methoxy-2-nitro-			Scheme E
	benzoic acid
Compound 1020	5-Methoxy-2-nitro-			Scheme E
	benzoic acid
Compound 1021	5-Methoxy-2-nitro-			Scheme E
	benzoic acid
Compound 1022	5-Methoxy-2-nitro-			Scheme E
	benzoic acid
Compound 1023	5-Methoxy-2-nitro-			Scheme E
	benzoic acid
Compound 1024	5-Methoxy-2-nitro-			Scheme E
	benzoic acid
Compound 1025	5-Hydroxy-2-nitro-	1-Bromo-2-		Scheme B
	benzoic acid	methoxy-ethane
Compound 1026	5-Hydroxy-2-nitro-	1-Bromo-2-		Scheme B
	benzoic acid	methoxy-ethane
Compound 1027	5-Hydroxy-2-nitro-	1-Bromo-2-		Scheme B
	benzoic acid	methoxy-ethane
Compound 1028	3,4-Dihydroxy-	1-Bromo-2-		Scheme F
	benzoic acid ethyl	methoxy-ethane
	ester
Compound 1029	3,4-Dihydroxy-	1-Bromo-2-		Scheme F
	benzoic acid ethyl	methoxy-ethane
	ester
Compound 1030	3,4-Dihydroxy-	1-Bromo-2-		Scheme F
	benzoic acid ethyl	methoxy-ethane
	ester
Compound 1031	3,4-Dihydroxy-	1-Bromo-2-		Scheme F
	benzoic acid ethyl	methoxy-ethane
	ester
Compound 1032	3,4-Dihydroxy-	1-Bromo-2-		Scheme F
	benzoic acid ethyl	methoxy-ethane
	ester
Compound 1033	5-Hydroxy-2-nitro-	1-Bromo-2-(2-		Scheme B
	benzoic acid	methoxy-ethoxy)-
		ethane
Compound 1034	5-Hydroxy-2-nitro-	1-Bromo-2-(2-		Scheme B
	benzoic acid	methoxy-ethoxy)-
		ethane
Compound 1035	5-Hydroxy-2-nitro-	1-Bromo-2-(2-		Scheme B
	benzoic acid	methoxy-ethoxy)-
		ethane
Compound 1036	5-Hydroxy-2-nitro-	1-Bromo-2-(2-		Scheme B
	benzoic acid	methoxy-ethoxy)-
		ethane
Compound 1037	5-Hydroxy-2-nitro-	1-Bromo-2-(2-		Scheme B
	benzoic acid	methoxy-ethoxy)-
		ethane
Compound 1038	5-Hydroxy-2-nitro-	1-Bromo-3-	Piperidine	Scheme C
	benzoic acid	chloropropane
Compound 1039	5-Hydroxy-2-nitro-	1-Bromo-3-	Piperidine	Scheme C
	benzoic acid	chloropropane
Compound 1040	5-Hydroxy-2-nitro-	1-Bromo-3-	Piperidine	Scheme C
	benzoic acid	chloropropane
Compound 1041	5-Hydroxy-2-nitro-	1-Bromo-3-	Piperidine	Scheme C
	benzoic acid	chloropropane
Compound 1042	5-Hydroxy-2-nitro-	1-Bromo-2-	Piperidine	Scheme C
	benzoic acid	chloroethane
Compound 1043	5-Hydroxy-2-nitro-	1-Bromo-2-	Piperidine	Scheme C
	benzoic acid	chloroethane
Compound 1044	5-Hydroxy-2-nitro-	1-Bromo-2-	Piperidine	Scheme C
	benzoic acid	chloroethane
Compound 1045	5-Hydroxy-2-nitro-	1-Bromo-2-	Piperidine	Scheme C
	benzoic acid	chloroethane
Compound 1046	5-Hydroxy-2-nitro-	Bromomethyl-		Scheme B
	benzoic acid	cyclohexane
Compound 1047	5-Hydroxy-2-nitro-	Bromomethyl-		Scheme B
	benzoic acid	cyclohexane
Compound 1048	5-Hydroxy-2-nitro-	Bromomethyl-		Scheme B
	benzoic acid	cyclohexane
Compound 1049	5-Hydroxy-2-nitro-	Bromomethyl-		Scheme B
	benzoic acid	cyclohexane
Compound 1050	5-Hydroxy-2-nitro-	Bromomethyl-		Scheme B
	benzoic acid	cyclohexane
Compound 1051	5-Hydroxy-2-nitro-	1-Bromo-4-fluoro-		Scheme B
	benzoic acid	butane
Compound 1052	5-Hydroxy-2-nitro-	1-Bromo-4-fluoro-		Scheme B
	benzoic acid	butane
Compound 1053	5-Hydroxy-2-nitro-	1-Bromo-4-fluoro-		Scheme B
	benzoic acid	butane
Compound 1054	5-Hydroxy-2-nitro-	1-Bromo-4-fluoro-		Scheme B
	benzoic acid	butane
Compound 1055	5-Hydroxy-2-nitro-	1-Bromo-4-fluoro-		Scheme B
	benzoic acid	butane
Compound 1057	5-Hydroxy-2-nitro-	1-Bromo-4-fluoro-		Scheme B
	benzoic acid	butane
Compound 1058	5-Hydroxy-2-nitro-	1-Bromo-4-fluoro-		Scheme B
	benzoic acid	butane
Compound 1059	5-Hydroxy-2-nitro-	1-Bromo-4-fluoro-		Scheme B
	benzoic acid	butane
Compound 1060	5-Hydroxy-2-nitro-	1-Bromo-4-fluoro-		Scheme B
	benzoic acid	butane
Compound 1061	5-Hydroxy-2-nitro-	1-Bromo-4-fluoro-		Scheme B
	benzoic acid	butane
Compound 1062	5-Chloro-2-nitro-	4-Hydroxy-		Scheme A
	benzoic acid	piperidine
Compound 1063	5-Chloro-2-nitro-	4-Piperidine-		Scheme A
	benzoic acid	methanol
Compound 1064	5-Chloro-2-nitro-	Morpholine		Scheme A
	benzoic acid
Compound 1065	5-Chloro-2-nitro-	Morpholine		Scheme A
	benzoic acid
Compound 1066	5-Chloro-2-nitro-	Morpholine		Scheme A
	benzoic acid
Compound 1067	5-Chloro-2-nitro-	4-Piperidino-		Scheme A
	benzoic acid	piperidine
Compound 1068	5-Chloro-2-nitro-	4-Piperidino-		Scheme A
	benzoic acid	piperidine
Compound 1069	5-Chloro-2-nitro-	4-Methylpiperidine		Scheme A
	benzoic acid
Compound 1070	5-Chloro-2-nitro-	4-Methylpiperidine		Scheme A
	benzoic acid
Compound 1071	5-Chloro-2-nitro-	4-Methylpiperidine		Scheme A
	benzoic acid
Compound 1072	5-Chloro-2-nitro-	4-Methylpiperazine		Scheme A
	benzoic acid
Compound 1073	5-Chloro-2-nitro-	4-Methylpiperazine		Scheme A
	benzoic acid
Compound 1074	5-Chloro-2-nitro-	Morpholine		Scheme A
	benzoic acid
Compound 1075	5-Chloro-2-nitro-	Morpholine		Scheme A
	benzoic acid
Compound 1076	5-Chloro-2-nitro-	Morpholine		Scheme A
	benzoic acid
Compound 935	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 936	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 937	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 938	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 939	5-Chloro-2-nitro-	Morpholine		Scheme A
	benzoic acid
Compound 940	5-Chloro-2-nitro-	Morpholine		Scheme A
	benzoic acid
Compound 941	5-Chloro-2-nitro-	Morpholine		Scheme A
	benzoic acid
Compound 942	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 944	5-Amino-2-nitro-	4-Chloro-butyryl		Scheme D
	benzoic acid	chloride
Compound 945	5-Amino-2-nitro-	4-Chloro-butyryl		Scheme D
	benzoic acid	chloride
Compound 946	5-Amino-2-nitro-	4-Chloro-butyryl		Scheme D
	benzoic acid	chloride
Compound 947	5-Amino-2-nitro-	4-Chloro-butyryl		Scheme D
	benzoic acid	chloride
Compound 948	5-Amino-2-nitro-	4-Chloro-butyryl		Scheme D
	benzoic acid	chloride
Compound 958	5-Chloro-2-nitro-	Piperidine		Scheme A
	benzoic acid
Compound 959	3-Amino-			Scheme G
	naphthalene-2-
	carboxylic acid
Compound 960	3-Amino-			Scheme G
	naphthalene-2-
	carboxylic acid
Compound 961	3-Amino-			Scheme G
	naphthalene-2-
	carboxylic acid
Compound 962	3-Amino-			Scheme G
	naphthalene-2-
	carboxylic acid
Compound 963	3-Amino-			Scheme G
	naphthalene-2-
	carboxylic acid
Compound 964	2-Almino-nicotinoic			Scheme G
	acid
Compound 965	2-Almino-nicotinoic			Scheme G
	acid
Compound 966	2-Amino-nicotinoic			Scheme G
	acid
Compound 967	2-Amino-nicotinoic			Scheme G
	acid
Compound 968	2-Amino-nicotinoic			Scheme G
	acid
Compound 969	3-Amino-			Scheme G
	naphthalene-2-
	carboxylic acid
Compound 970	3-Amino-			Scheme G
	naphthalene-2-
	carboxylic acid
Compound 971	3-Amino-			Scheme G
	naphthalene-2-
	carboxylic acid
Compound 972	3-Amino-			Scheme G
	naphthalene-2-
	carboxylic acid
Compound 973	3-Amino-			Scheme G
	naphthalene-2-
	carboxylic acid
Compound 985	2-Amino-5-fluoro-			Scheme G
	benzoic acid
Compound 986	2-Amino-5-fluoro-			Scheme G
	benzoic acid
Compound 987	2-Amino-5-fluoro-			Scheme G
	benzoic acid
Compound 988	2-Amino-5-fluoro-			Scheme G
	benzoic acid
Compound 989	2-Amino-5-fluoro-			Scheme G
	benzoic acid
Compound 990	2-Amino-5-fluoro-			Scheme G
	benzoic acid
Compound 1013	3,4-Dihydroxy-	1-Bromo-2-		Scheme F
	benzoic acid ethyl	methoxy-ethane
	ester
Compound 1014	3,4-Dihydroxy-	1-Bromo-2-		Scheme F
	benzoic acid ethyl	methoxy-ethane
	ester
Compound 1015	3,4-Dihydroxy-	1-Bromo-2-		Scheme F
	benzoic acid ethyl	methoxy-ethane
	ester
Compound 1016	3,4-Dihydroxy-	1-Bromo-2-		Scheme F
	benzoic acid ethyl	methoxy-ethane
	ester
Compound 1017	5-Methoxy-2-nitro-			Scheme E
	benzoic acid
Compound 1018	5-Methoxy-2-nitro-			Scheme E
	benzoic acid
Compound 1019	5-Methoxy-2-nitro-			Scheme E
	benzoic acid
Compound 1020	5-Methoxy-2-nitro-			Scheme E
	benzoic acid
Compound 1021	5-Methoxy-2-nitro-			Scheme E
	benzoic acid
Compound 1022	5-Methoxy-2-nitro-			Scheme E
	benzoic acid
Compound 1023	5-Methoxy-2-nitro-			Scheme E
	benzoic acid
Compound 1024	5-Methoxy-2-nitro-			Scheme E
	benzoic acid
Compound 1025	5-Hydroxy-2-nitro-	1-Bromo-2-		Scheme B
	benzoic acid	methoxy-ethane
Compound 1026	5-Hydroxy-2-nitro-	1-Bromo-2-		Scheme B
	benzoic acid	methoxy-ethane
Compound 1027	5-Hydroxy-2-nitro-	1-Bromo-2-		Scheme B
	benzoic acid	methoxy-ethane
Compound 1028	3,4-Dihydroxy-	1-Bromo-2-		Scheme F
	benzoic acid ethyl	methoxy-ethane
	ester
Compound 1029	3,4-Dihydroxy-	1-Bromo-2-		Scheme F
	benzoic acid ethyl	methoxy-ethane
	ester
Compound 1030	3,4-Dihydroxy-	1-Bromo-2-		Scheme F
	benzoic acid ethyl	methoxy-ethane
	ester
Compound 1031	3,4-Dihydroxy-	1-Bromo-2-		Scheme F
	benzoic acid ethyl	methoxy-ethane
	ester
Compound 1032	3,4-Dihydroxy-	1-Bromo-2-		Scheme F
	benzoic acid ethyl	methoxy-ethane
	ester
Compound 1033	5-Hydroxy-2-nitro-	1-Bromo-2-(2-		Scheme B
	benzoic acid	methoxy-ethoxy)-
		ethane
Compound 1034	5-Hydroxy-2-nitro-	1-Bromo-2-(2-		Scheme B
	benzoic acid	methoxy-ethoxy)-
		ethane
Compound 1035	5-Hydroxy-2-nitro-	1-Bromo-2-(2-		Scheme B
	benzoic acid	methoxy-ethoxy)-
		ethane
Compound 1036	5-Hydroxy-2-nitro-	1-Bromo-2-(2-		Scheme B
	benzoic acid	methoxy-ethoxy)-
		ethane
Compound 1037	5-Hydroxy-2-nitro-	1-Bromo-2-(2-		Scheme B
	benzoic acid	methoxy-ethoxy)-
		ethane
Compound 1038	5-Hydroxy-2-nitro-	1-Bromo-3-	Piperidine	Scheme C
	benzoic acid	chloropropane
Compound 1039	5-Hydroxy-2-nitro-	1-Bromo-3-	Piperidine	Scheme C
	benzoic acid	chloropropane
Compound 1040	5-Hydroxy-2-nitro-	1-Bromo-3-	Piperidine	Scheme C
	benzoic acid	chloropropane
Compound 1041	5-Hydroxy-2-nitro-	1-Bromo-3-	Piperidine	Scheme C
	benzoic acid	chloropropane
Compound 1042	5-Hydroxy-2-nitro-	1-Bromo-2-	Piperidine	Scheme C
	benzoic acid	chloroethane
Compound 1043	5-Hydroxy-2-nitro-	1-Bromo-2-	Piperidine	Scheme C
	benzoic acid	chloroethane
Compound 1044	5-Hydroxy-2-nitro-	1-Bromo-2-	Piperidine	Scheme C
	benzoic acid	chloroethane
Compound 1045	5-Hydroxy-2-nitro-	1-Bromo-2-	Piperidine	Scheme C
	benzoic acid	chloroethane
Compound 1046	5-Hydroxy-2-nitro-	Bromomethyl-		Scheme B
	benzoic acid	cyclohexane
Compound 1047	5-Hydroxy-2-nitro-	Bromomethyl-		Scheme B
	benzoic acid	cyclohexane
Compound 1048	5-Hydroxy-2-nitro-	Bromomethyl-		Scheme B
	benzoic acid	cyclohexane
Compound 1049	5-Hydroxy-2-nitro-	Bromomethyl-		Scheme B
	benzoic acid	cyclohexane
Compound 1050	5-Hydroxy-2-nitro-	Bromomethyl-		Scheme B
	benzoic acid	cyclohexane
Compound 1051	5-Hydroxy-2-nitro-	1-Bromo-4-fluoro-		Scheme B
	benzoic acid	butane
Compound 1052	5-Hydroxy-2-nitro-	1-Bromo-4-fluoro-		Scheme B
	benzoic acid	butane
Compound 1053	5-Hydroxy-2-nitro-	1-Bromo-4-fluoro-		Scheme B
	benzoic acid	butane
Compound 1054	5-Hydroxy-2-nitro-	1-Bromo-4-fluoro-		Scheme B
	benzoic acid	butane
Compound 1055	5-Hydroxy-2-nitro-	1-Bromo-4-fluoro-		Scheme B
	benzoic acid	butane
Compound 1057	5-Hydroxy-2-nitro-	1-Bromo-4-fluoro-		Scheme B
	benzoic acid	butane
Compound 1058	5-Hydroxy-2-nitro-	1-Bromo-4-fluoro-		Scheme B
	benzoic acid	butane
Compound 1059	5-Hydroxy-2-nitro-	1-Bromo-4-fluoro-		Scheme B
	benzoic acid	butane
Compound 1060	5-Hydroxy-2-nitro-	1-Bromo-4-fluoro-		Scheme B
	benzoic acid	butane
Compound 1061	5-Hydroxy-2-nitro-	1-Bromo-4-fluoro-		Scheme B
	benzoic acid	butane
Compound 1062	5-Chloro-2-nitro-	4-Hydroxy-		Scheme A
	benzoic acid	piperidine
Compound 1063	5-Chloro-2-nitro-	4-Piperidine-		Scheme A
	benzoic acid	methanol
Compound 1064	5-Chloro-2-nitro-	Morpholine		Scheme A
	benzoic acid
Compound 1065	5-Chloro-2-nitro-	Morpholine		Scheme A
	benzoic acid
Compound 1066	5-Chloro-2-nitro-	Morpholine		Scheme A
	benzoic acid
Compound 1067	5-Chloro-2-nitro-	4-Piperidino-		Scheme A
	benzoic acid	piperidine
Compound 1068	5-Chloro-2-nitro-	4-Piperidino-		Scheme A
	benzoic acid	piperidine
Compound 1069	5-Chloro-2-nitro-	4-Methylpiperidine		Scheme A
	benzoic acid
Compound 1070	5-Chloro-2-nitro-	4-Methylpiperidine		Scheme A
	benzoic acid
Compound 1071	5-Chloro-2-nitro-	4-Methylpiperidine		Scheme A
	benzoic acid
Compound 1072	5-Chloro-2-nitro-	4-Methylpiperazine		Scheme A
	benzoic acid
Compound 1073	5-Chloro-2-nitro-	4-Methylpiperazine		Scheme A
	benzoic acid
Compound 1074	5-Chloro-2-nitro-	Morpholine		Scheme A
	benzoic acid
Compound 1075	5-Chloro-2-nitro-	Morpholine		Scheme A
	benzoic acid
Compound 1076	5-Chloro-2-nitro-	Morpholine		Scheme A
	benzoic acid

TABLE 3
Structures of compounds 1 to 1077 are shown in Table 3.
Compound No. Chemical structural formula
Compound 1
Compound 2
Compound 3
Compound 1
Compound 5
Compound 6
Compound 7
Compound 8
Compound 9
Compound 10
Compound 11
Compound 12
Compound 13
Compound 14
Compound 15
Compound 16
Compound 17
Compound 18
Compound 19
Compound 20
Compound 21
Compound 22
Compound 23
Compound 24
Compound 25
Compound 26
Compound 27
Compound 28
Compound 29
Compound 30
Compound 31
Compound 32
Compound 33
Compound 34
Compound 35
Compound 36
Compound 37
Compound 38
Compound 39
Compound 40
Compound 41
Compound 42
Compound 43
Compound 44
Compound 45
Compound 46
Compound 47
Compound 48
Compound 49
Compound 50
Compound 51
Compound 52
Compound 53
Compound 54
Compound 55
Compound 56
Compound 57
Compound 58
Compound 59
Compound 60
Compound 61
Compound 62
Compound 63
Compound 64
Compound 65
Compound 66
Compound 67
Compound 68
Compound 69
Compound 70
Compound 71
Compound 72
Compound 73
Compound 74
Compound 75
Compound 76
Compound 77
Compound 78
Compound 79
Compound 80
Compound 81
Compound 82
Compound 83
Compound 84
Compound 85
Compound 86
Compound 87
Compound 88
Compound 89
Compound 90
Compound 91
Compound 92
Compound 93
Compound 94
Compound 95
Compound 96
Compound 97
Compound 98
Compound 99
Compound 100
Compound 101
Compound 102
Compound 103
Compound 104
Compound 105
Compound 106
Compound 107
Compound 108
Compound 109
Compound 110
Compound 111
Compound 112
Compound 113
Compound 114
Compound 115
Compound 116
Compound 117
Compound 118
Compound 119
Compound 120
Compound 121
Compound 122
Compound 123
Compound 124
Compound 125
Compound 126
Compound 127
Compound 128
Compound 129
Compound 130
Compound 131
Compound 132
Compound 133
Compound 134
Compound 135
Compound 136
Compound 137
Compound 138
Compound 139
Compound 140
Compound 141
Compound 142
Compound 143
Compound 144
Compound 145
Compound 146
Compound 147
Compound 148
Compound 149
Compound 150
Compound 151
Compound 152
Compound 153
Compound 154
Compound 155
Compound 156
Compound 157
Compound 158
Compound 159
Compound 160
Compound 161
Compound 162
Compound 163
Compound 164
Compound 165
Compound 166
Compound 167
Compound 168
Compound 169
Compound 170
Compound 171
Compound 172
Compound 173
Compound 174
Compound 175
Compound 176
Compound 177
Compound 178
Compound 179
Compound 180
Compound 181
Compound 182
Compound 183
Compound 184
Compound 185
Compound 186
Compound 187
Compound 188
Compound 189
Compound 190
Compound 191
Compound 192
Compound 193
Compound 194
Compound 195
Compound 196
Compound 197
Compound 198
Compound 199
Compound 200
Compound 201
Compound 202
Compound 203
Compound 204
Compound 205
Compound 206
Compound 207
Compound 208
Compound 209
Compound 210
Compound 211
Compound 212
Compound 213
Compound 214
Compound 215
Compound 216
Compound 217
Compound 218
Compound 219
Compound 220
Compound 221
Compound 222
Compound 223
Compound 224
Compound 225
Compound 226
Compound 227
Compound 228
Compound 229
Compound 230
Compound 231
Compound 232
Compound 233
Compound 234
Compound 235
Compound 236
Compound 237
Compound 238
Compound 239
Compound 240
Compound 241
Compound 242
Compound 243
Compound 244
Compound 245
Compound 246
Compound 247
Compound 248
Compound 249
Compound 250
Compound 251
Compound 252
Compound 253
Compound 255
Compound 256
Compound 257
Compound 258
Compound 259
Compound 260
Compound 261
Compound 262
Compound 263
Compound 264
Compound 265
Compound 266
Compound 267
Compound 268
Compound 269
Compound 270
Compound 271
Compound 272
Compound 273
Compound 274
Compound 275
Compound 276
Compound 277
Compound 278
Compound 279
Compound 280
Compound 281
Compound 282
Compound 283
Compound 284
Compound 285
Compound 286
Compound 287
Compound 288
Compound 289
Compound 290
Compound 291
Compound 292
Compound 293
Compound 294
Compound 295
Compound 296
Compound 297
Compound 298
Compound 299
Compound 300
Compound 301
Compound 302
Compound 303
Compound 304
Compound 305
Compound 306
Compound 307
Compound 308
Compound 309
Compound 310
Compound 311
Compound 312
Compound 313
Compound 314
Compound 315
Compound 316
Compound 317
Compound 318
Compound 319
Compound 320
Compound 321
Compound 322
Compound 323
Compound 324
Compound 325
Compound 326
Compound 327
Compound 328
Compound 329
Compound 330
Compound 331
Compound 332
Compound 333
Compound 334
Compound 335
Compound 336
Compound 337
Compound 338
Compound 339
Compound 340
Compound 341
Compound 342
Compound 343
Compound 344
Compound 345
Compound 346
Compound 347
Compound 348
Compound 349
Compound 350
Compound 351
Compound 352
Compound 353
Compound 354
Compound 355
Compound 356
Compound 357
Compound 358
Compound 359
Compound 360
Compound 361
Compound 362
Compound 363
Compound 364
Compound 366
Compound 367
Compound 368
Compound 369
Compound 370
Compound 371
Compound 372
Compound 373
Compound 374
Compound 375
Compound 376
Compound 377
Compound 378
Compound 379
Compound 380
Compound 381
Compound 382
Compound 383
Compound 384
Compound 385
Compound 386
Compound 387
Compound 388
Compound 389
Compound 390
Compound 391
Compound 392
Compound 393
Compound 394
Compound 395
Compound 396
Compound 397
Compound 398
Compound 399
Compound 400
Compound 401
Compound 402
Compound 403
Compound 404
Compound 405
Compound 406
Compound 407
Compound 408
Compound 409
Compound 410
Compound 411
Compound 412
Compound 413
Compound 414
Compound 415
Compound 416
Compound 417
Compound 418
Compound 419
Compound 420
Compound 421
Compound 422
Compound 423
Compound 424
Compound 425
Compound 426
Compound 427
Compound 428
Compound 429
Compound 430
Compound 431
Compound 432
Compound 433
Compound 434
Compound 435
Compound 436
Compound 437
Compound 438
Compound 439
Compound 440
Compound 441
Compound 442
Compound 443
Compound 444
Compound 445
Compound 446
Compound 447
Compound 448
Compound 449
Compound 450
Compound 451
Compound 452
Compound 453
Compound 454
Compound 455
Compound 456
Compound 457
Compound 458
Compound 459
Compound 460
Compound 461
Compound 462
Compound 463
Compound 464
Compound 465
Compound 466
Compound 467
Compound 468
Compound 469
Compound 470
Compound 471
Compound 472
Compound 473
Compound 474
Compound 475
Compound 476
Compound 477
Compound 478
Compound 479
Compound 480
Compound 481
Compound 482
Compound 483
Compound 484
Compound 485
Compound 486
Compound 487
Compound 488
Compound 489
Compound 490
Compound 491
Compound 492
Compound 493
Compound 494
Compound 495
Compound 496
Compound 497
Compound 498
Compound 499
Compound 500
Compound 501
Compound 502
Compound 503
Compound 504
Compound 505
Compound 506
Compound 507
Compound 508
Compound 509
Compound 510
Compound 511
Compound 512
Compound 513
Compound 514
Compound 515
Compound 516
Compound 517
Compound 518
Compound 519
Compound 521
Compound 522
Compound 523
Compound 524
Compound 525
Compound 526
Compound 527
Compound 528
Compound 529
Compound 530
Compound 531
Compound 532
Compound 533
Compound 534
Compound 535
Compound 536
Compound 537
Compound 538
Compound 539
Compound 540
Compound 541
Compound 542
Compound 543
Compound 544
Compound 545
Compound 546
Compound 547
Compound 548
Compound 549
Compound 550
Compound 551
Compound 552
Compound 553
Compound 554
Compound 555
Compound 556
Compound 557
Compound 558
Compound 559
Compound 560
Compound 561
Compound 562
Compound 563
Compound 564
Compound 565
Compound 566
Compound 567
Compound 568
Compound 569
Compound 570
Compound 571
Compound 572
Compound 573
Compound 574
Compound 575
Compound 576
Compound 577
Compound 578
Compound 579
Compound 580
Compound 581
Compound 582
Compound 583
Compound 584
Compound 585
Compound 586
Compound 587
Compound 588
Compound 589
Compound 590
Compound 591
Compound 592
Compound 593
Compound 594
Compound 595
Compound 596
Compound 597
Compound 598
Compound 599
Compound 600
Compound 601
Compound 602
Compound 603
Compound 604
Compound 605
Compound 606
Compound 607
Compound 608
Compound 609
Compound 610
Compound 611
Compound 612
Compound 613
Compound 614
Compound 615
Compound 616
Compound 617
Compound 618
Compound 619
Compound 620
Compound 621
Compound 622
Compound 623
Compound 624
Compound 625
Compound 626
Compound 627
Compound 628
Compound 629
Compound 630
Compound 631
Compound 632
Compound 633
Compound 634
Compound 635
Compound 636
Compound 637
Compound 638
Compound 639
Compound 640
Compound 641
Compound 642
Compound 643
Compound 644
Compound 645
Compound 646
Compound 647
Compound 648
Compound 649
Compound 650
Compound 651
Compound 652
Compound 653
Compound 654
Compound 655
Compound 656
Compound 657
Compound 658
Compound 659
Compound 660
Compound 661
Compound 662
Compound 663
Compound 664
Compound 665
Compound 666
Compound 667
Compound 668
Compound 669
Compound 670
Compound 671
Compound 672
Compound 673
Compound 674
Compound 675
Compound 676
Compound 677
Compound 678
Compound 679
Compound 680
Compound 681
Compound 682
Compound 683
Compound 684
Compound 685
Compound 686
Compound 687
Compound 688
Compound 689
Compound 690
Compound 691
Compound 692
Compound 693
Compound 694
Compound 695
Compound 696
Compound 697
Compound 698
Compound 699
Compound 700
Compound 701
Compound 702
Compound 703
Compound 704
Compound 705
Compound 706
Compound 707
Compound 708
Compound 709
Compound 710
Compound 711
Compound 712
Compound 713
Compound 714
Compound 715
Compound 716
Compound 717
Compound 718
Compound 719
Compound 720
Compound 721
Compound 722
Compound 723
Compound 724
Compound 725
Compound 726
Compound 727
Compound 728
Compound 729
Compound 730
Compound 731
Compound 732
Compound 733
Compound 734
Compound 735
Compound 736
Compound 737
Compound 738
Compound 739
Compound 740
Compound 741
Compound 742
Compound 743
Compound 744
Compound 745
Compound 746
Compound 747
Compound 748
Compound 749
Compound 750
Compound 751
Compound 752
Compound 753
Compound 754
Compound 755
Compound 756
Compound 757
Compound 758
Compound 759
Compound 760
Compound 761
Compound 762
Compound 763
Compound 764
Compound 765
Compound 766
Compound 767
Compound 768
Compound 769
Compound 770
Compound 771
Compound 772
Compound 773
Compound 774
Compound 775
Compound 776
Compound 777
Compound 778
Compound 779
Compound 780
Compound 781
Compound 782
Compound 783
Compound 784
Compound 785
Compound 786
Compound 787
Compound 788
Compound 789
Compound 790
Compound 791
Compound 792
Compound 793
Compound 794
Compound 795
Compound 796
Compound 797
Compound 798
Compound 799
Compound 800
Compound 801
Compound 802
Compound 803
Compound 804
Compound 805
Compound 806
Compound 807
Compound 808
Compound 809
Compound 810
Compound 811
Compound 812
Compound 813
Compound 814
Compound 815
Compound 816
Compound 817
Compound 818
Compound 819
Compound 820
Compound 821
Compound 822
Compound 823
Compound 824
Compound 825
Compound 826
Compound 827
Compound 828
Compound 829
Compound 830
Compound 831
Compound 832
Compound 833
Compound 834
Compound 835
Compound 836
Compound 837
Compound 838
Compound 839
Compound 840
Compound 841
Compound 842
Compound 843
Compound 844
Compound 845
Compound 846
Compound 847
Compound 848
Compound 849
Compound 850
Compound 851
Compound 852
Compound 853
Compound 854
Compound 855
Compound 856
Compound 857
Compound 858
Compound 859
Compound 860
Compound 861
Compound 862
Compound 863
Compound 864
Compound 865
Compound 866
Compound 867
Compound 868
Compound 869
Compound 870
Compound 871
Compound 872
Compound 873
Compound 874
Compound 875
Compound 876
Compound 877
Compound 878
Compound 879
Compound 880
Compound 881
Compound 882
Compound 883
Compound 884
Compound 885
Compound 886
Compound 887
Compound 888
Compound 889
Compound 890
Compound 891
Compound 892
Compound 893
Compound 894
Compound 895
Compound 896
Compound 897
Compound 898
Compound 899
Compound 900
Compound 901
Compound 902
Compound 903
Compound 904
Compound 905
Compound 906
Compound 907
Compound 908
Compound 909
Compound 910
Compound 911
Compound 912
Compound 913
Compound 914
Compound 915
Compound 916
Compound 917
Compound 918
Compound 919
Compound 920
Compound 921
Compound 922
Compound 923
Compound 924
Compound 925
Compound 926
Compound 927
Compound 928
Compound 929
Compound 930
Compound 931
Compound 932
Compound 933
Compound 934
Compound 935
Compound 936
Compound 937
Compound 938
Compound 939
Compound 940
Compound 941
Compound 942
Compound 943
Compound 944
Compound 945
Compound 946
Compound 947
Compound 948
Compound 949
Compound 950
Compound 951
Compound 952
Compound 953
Compound 954
Compound 955
Compound 956
Compound 957
Compound 958
Compound 959
Compound 960
Compound 961
Compound 962
Compound 963
Compound 964
Compound 965
Compound 966
Compound 967
Compound 968
Compound 969
Compound 970
Compound 971
Compound 972
Compound 973
Compound 974
Compound 975
Compound 976
Compound 977
Compound 978
Compound 979
Compound 980
Compound 981
Compound 982
Compound 983
Compound 984
Compound 985
Compound 986
Compound 987
Compound 988
Compound 989
Compound 990
Compound 991
Compound 992
Compound 993
Compound 995
Compound 996
Compound 997
Compound 998
Compound 999
Compound 1000
Compound 1001
Compound 1002
Compound 1003
Compound 1004
Compound 1005
Compound 1006
Compound 1007
Compound 1008
Compound 1009
Compound 1010
Compound 1011
Compound 1012
Compound 1013
Compound 1014
Compound 1015
Compound 1016
Compound 1017
Compound 1018
Compound 1019
Compound 1020
Compound 1021
Compound 1022
Compound 1023
Compound 1024
Compound 1025
Compound 1026
Compound 1027
Compound 1028
Compound 1029
Compound 1030
Compound 1031
Compound 1032
Compound 1033
Compound 1034
Compound 1035
Compound 1036
Compound 1037
Compound 1038
Compound 1039
Compound 1040
Compound 1041
Compound 1042
Compound 1043
Compound 1044
Compound 1045
Compound 1046
Compound 1047
Compound 1048
Compound 1049
Compound 1050
Compound 1051
Compound 1052
Compound 1053
Compound 1054
Compound 1055
Compound 1056
Compound 1057
Compound 1058
Compound 1059
Compound 1060
Compound 1061
Compound 1062
Compound 1063
Compound 1064
Compound 1065
Compound 1066
Compound 1067
Compound 1068
Compound 1069
Compound 1070
Compound 1071
Compound 1072
Compound 1073
Compound 1074
Compound 1075
Compound 1076
Compound 1077

Pharmacological Test Example 1

Experiment of Sodium-Dependent Phosphate Uptake of Xenopus oocytes Which Expressed NaPi-2b

Degenerate primers were prepared from sequences of mouse NaPi-2b disclosed in Hilfiker H. et al., Pro Natl Acad Sci USA, 95 (24): 14564-14569, 1988 and sequences of human and rat NaPi-2a disclosed in Magagnin S. et al., Proc Natl Aca Sci USA, 90 (13): 5979-5983, 1993. RNA was extracted from the rat small intestine using ISOGEN; manufactured by NIPPON GENE CO., LTD (Japan). 400 bp gene fragments were obtained by PCR using, as a template, a cDNA library prepared with a cDNA synthesis kit (manufactured by STRATAGENE (US)). Thereafter, the above rat small intestine cDNA library was screened using the gene fragment as a probe, and the whole gene sequence of rat NaPi-2b was cloned. cRNA was synthesized from the cloned rat NaPi-2b cDNA with a cRNA synthesis kit (manufactured by Ambion (US)). The synthesized cRNA was injected into Xenopus oocytes (obtained from COPACETIC (Japan)) with a liquid microinjector (manufactured by Drummond (US)) and was cultured for 2 days to express rat NaPi-2b. Thereafter, for a group of derivatives, phosphate uptake inhibitory activity were measured using the Xenopus oocytes with ³²P radioactive phosphorus (manufactured by Daiichi Kagaku Inc. (Japan)). As a result, it was found that these compounds had inhibitory activity with IC₅₀ values as shown in Table 4. IC₅₀ values were determined by determining an inhibition curve by an approximation formula using the least square from inhibitory activity values obtained from five concentration levels of the compound and determining the concentration of the compound which exhibits 50% of the maximum inhibitory activity. The inhibitory activity for 300 μM and 100 μM was determined from the same inhibition curve and expressed in percentage inhibition (%) in Table 5.

TABLE 4
Compound No.  IC50 (μM)
Compound 1    9.11
Compound 3    7.15
Compound 4    79.93
Compound 5    3.31
Compound 6    5.38
Compound 7    7.15
Compound 8    1.72
Compound 9    4.26
Compound 10   26.12
Compound 11   8.21
Compound 12   4.51
Compound 13   9.22
Compound 14   12.10
Compound 15   1.41
Compound 16   2.30
Compound 17   3.59
Compound 18   4.03
Compound 19   8.16
Compound 20   2.83
Compound 21   21.53
Compound 22   26.67
Compound 23   9.88
Compound 24   20.92
Compound 25   23.91
Compound 26   25.37
Compound 27   3.63
Compound 28   5.12
Compound 29   0.55
Compound 30   7.86
Compound 31   0.58
Compound 32   1.95
Compound 33   15.02
Compound 34   1.50
Compound 35   3.23
Compound 36   4.04
Compound 37   13.47
Compound 38   5.64
Compound 39   9.24
Compound 40   2.03
Compound 41   2.43
Compound 42   8.21
Compound 43   20.66
Compound 44   4.71
Compound 45   26.14
Compound 46   7.41
Compound 47   4.38
Compound 48   2.07
Compound 49   3.37
Compound 50   19.48
Compound 51   4.60
Compound 52   10.39
Compound 53   4.05
Compound 54   6.45
Compound 55   0.86
Compound 56   0.89
Compound 57   1.02
Compound 58   7.67
Compound 59   1.22
Compound 60   1.58
Compound 61   0.31
Compound 62   0.90
Compound 63   5.97
Compound 64   3.77
Compound 65   1.29
Compound 66   0.89
Compound 67   0.65
Compound 68   0.36
Compound 69   3.93
Compound 70   9.51
Compound 71   12.33
Compound 72   10.41
Compound 73   1.75
Compound 74   2.15
Compound 75   12.77
Compound 76   13.17
Compound 77   3.01
Compound 78   7.17
Compound 79   2.87
Compound 80   10.87
Compound 81   5.65
Compound 82   6.03
Compound 83   2.98
Compound 84   8.42
Compound 85   2.00
Compound 86   11.4
Compound 87   0.29
Compound 88   0.22
Compound 89   1.11
Compound 90   3.42
Compound 91   0.22
Compound 92   0.26
Compound 93   10.98
Compound 94   5.63
Compound 95   1.27
Compound 96   5.94
Compound 97   0.51
Compound 98   0.62
Compound 99   3.03
Compound 100  0.64
Compound 101  0.75
Compound 102  5.58
Compound 103  5.73
Compound 104  11.34
Compound 105  7.29
Compound 106  5.11
Compound 107  1.08
Compound 108  3.83
Compound 109  6.18
Compound 110  7.70
Compound 111  9.12
Compound 112  41.98
Compound 113  17.91
Compound 114  2.55
Compound 115  5.48
Compound 116  7.01
Compound 117  0.58
Compound 118  6.07
Compound 119  0.74
Compound 120  2.55
Compound 121  4.06
Compound 122  <3.00
Compound 123  3.77
Compound 124  3.15
Compound 125  136.43
Compound 126  6.43
Compound 127  11.59
Compound 128  11.61
Compound 129  13.70
Compound 130  11.42
Compound 132  0.75
Compound 133  0.88
Compound 134  7.82
Compound 135  3.74
Compound 136  4.52
Compound 137  3.00
Compound 138  4.47
Compound 139  55.50
Compound 140  74.24
Compound 141  5.78
Compound 142  9.20
Compound 143  5.88
Compound 144  5.02
Compound 145  3.82
Compound 146  1.99
Compound 147  7.68
Compound 148  15.63
Compound 149  5.51
Compound 150  1.09
Compound 151  3.07
Compound 152  1.48
Compound 153  3.50
Compound 154  2.37
Compound 155  0.32
Compound 156  0.46
Compound 157  7.19
Compound 158  3.28
Compound 159  4.35
Compound 160  0.93
Compound 161  0.96
Compound 162  3.11
Compound 163  1.60
Compound 164  4.76
Compound 165  2.43
Compound 166  27.85
Compound 167  30.20
Compound 168  4.84
Compound 169  4.24
Compound 170  5.34
Compound 171  5.12
Compound 172  2.74
Compound 173  7.40
Compound 174  12.54
Compound 175  3.57
Compound 176  4.10
Compound 177  26.01
Compound 178  7.54
Compound 179  18.69
Compound 180  <3.00
Compound 181  3.16
Compound 182  10.24
Compound 183  <3.00
Compound 184  4.01
Compound 185  2.02
Compound 186  10.1
Compound 187  7.87
Compound 188  19.43
Compound 189  1.47
Compound 190  20.32
Compound 191  12.12
Compound 192  23.09
Compound 193  4.21
Compound 194  7.36
Compound 195  0.98
Compound 196  0.61
Compound 197  4.87
Compound 198  2.71
Compound 199  1.82
Compound 200  0.39
Compound 201  11.10
Compound 202  3.14
Compound 203  <3.00
Compound 204  <3.00
Compound 205  <3.00
Compound 206  <3.00
Compound 207  <1.00
Compound 208  <0.30
Compound 209  <1.00
Compound 210  34.96
Compound 211  69.07
Compound 212  71.27
Compound 213  16.64
Compound 214  3.95
Compound 215  <3.00
Compound 216  21.82
Compound 217  11.21
Compound 218  4.05
Compound 219  9.07
Compound 220  9.42
Compound 221  9.51
Compound 222  8.86
Compound 223  11.30
Compound 224  19.99
Compound 225  60.98
Compound 226  1.69
Compound 227  7.40
Compound 228  22.48
Compound 229  6.32
Compound 252  1.49
Compound 253  3.47
Compound 255  3.54
Compound 256  <10.00
Compound 257  <3.00
Compound 258  <3.00
Compound 259  <3.00
Compound 260  <3.00
Compound 261  <3.00
Compound 262  1.10
Compound 263  <1.00
Compound 264  <1.00
Compound 265  <1.00
Compound 266  <1.00
Compound 267  0.43
Compound 268  1.02
Compound 269  2.19
Compound 270  5.04
Compound 271  0.21
Compound 272  0.47
Compound 273  0.15
Compound 274  1.04
Compound 275  1.73
Compound 276  6.20
Compound 277  1.60
Compound 278  0.16
Compound 279  2.31
Compound 280  0.78
Compound 281  4.60
Compound 282  6.71
Compound 283  22.44
Compound 284  26.94
Compound 285  0.90
Compound 286  0.57
Compound 287  0.11
Compound 288  1.31
Compound 289  2.89
Compound 290  3.25
Compound 291  1.16
Compound 292  3.50
Compound 293  5.59
Compound 294  7.80
Compound 295  7.58
Compound 296  1.45
Compound 297  0.96
Compound 298  9.22
Compound 299  3.91
Compound 300  1.92
Compound 301  15.17
Compound 302  1.12
Compound 303  1.13
Compound 304  1.23
Compound 305  2.47
Compound 306  2.13
Compound 307  41.17
Compound 308  2.76
Compound 309  15.12
Compound 310  7.82
Compound 311  7.78
Compound 312  3.31
Compound 313  1.24
Compound 314  3.39
Compound 315  9.02
Compound 316  4.71
Compound 317  5.02
Compound 318  2.49
Compound 319  9.76
Compound 320  4.09
Compound 321  2.66
Compound 322  5.93
Compound 323  4.69
Compound 324  4.43
Compound 325  2.56
Compound 326  2.10
Compound 327  5.12
Compound 328  1.15
Compound 329  5.63
Compound 330  10.69
Compound 331  15.76
Compound 332  2.87
Compound 333  17.18
Compound 334  7.69
Compound 335  5.86
Compound 336  16.63
Compound 337  1.39
Compound 338  18.97
Compound 339  12.77
Compound 340  8.41
Compound 341  <3.00
Compound 342  32.60
Compound 343  124.10
Compound 344  30.99
Compound 345  129.95
Compound 346  4.46
Compound 347  4.91
Compound 348  16.59
Compound 349  8.78
Compound 350  25.32
Compound 351  8.96
Compound 352  13.00
Compound 353  8.85
Compound 354  1.54
Compound 356  0.17
Compound 358  54.07
Compound 359  7.10
Compound 360  0.63
Compound 361  <1.00
Compound 362  <1.00
Compound 363  <1.00
Compound 364  <1.00
Compound 367  6.88
Compound 368  1.37
Compound 369  1.45
Compound 370  1.86
Compound 371  2.54
Compound 372  0.80
Compound 373  1.68
Compound 374  9.25
Compound 375  24.71
Compound 376  21.00
Compound 377  9.65
Compound 378  4.35
Compound 379  0.97
Compound 380  0.35
Compound 381  1.00
Compound 382  1.04
Compound 383  1.98
Compound 384  0.25
Compound 385  0.31
Compound 386  <3.00
Compound 387  6.45
Compound 388  19.67
Compound 389  1.09
Compound 390  0.45
Compound 391  1.02
Compound 392  1.42
Compound 393  0.52
Compound 394  0.95
Compound 395  8.55
Compound 396  8.19
Compound 397  9.25
Compound 398  <0.30
Compound 399  3.67
Compound 400  <0.30
Compound 401  6.13
Compound 402  14.12
Compound 403  26.73
Compound 404  2.18
Compound 405  1.90
Compound 406  0.88
Compound 407  0.57
Compound 408  0.69
Compound 409  2.52
Compound 410  4.05
Compound 411  10.08
Compound 412  7.96
Compound 413  <3.00
Compound 414  <3.00
Compound 415  <3.00
Compound 416  3.25
Compound 417  <3.00
Compound 418  9.38
Compound 419  9.20
Compound 420  27.14
Compound 421  29.56
Compound 422  1.15
Compound 423  <3.00
Compound 424  1.79
Compound 425  <3.00
Compound 426  1.89
Compound 427  <3.00
Compound 428  1.82
Compound 429  5.88
Compound 430  4.53
Compound 431  5.57
Compound 432  22.22
Compound 433  14.34
Compound 434  7.78
Compound 435  7.65
Compound 436  8.36
Compound 437  <3.00
Compound 438  26.27
Compound 439  28.74
Compound 440  32.35
Compound 441  40.14
Compound 442  3.15
Compound 443  11.05
Compound 444  <3.00
Compound 445  10.33
Compound 446  1.54
Compound 447  2.16
Compound 448  9.41
Compound 449  21.73
Compound 450  16.94
Compound 451  37.84
Compound 452  <3.00
Compound 453  <3.00
Compound 454  <3.00
Compound 455  <3.00
Compound 456  <3.00
Compound 457  <3.00
Compound 458  <3.00
Compound 459  <3.00
Compound 460  <3.00
Compound 461  3.59
Compound 462  <3.00
Compound 463  4.44
Compound 464  5.00
Compound 465  7.43
Compound 466  <3.00
Compound 467  7.94
Compound 468  22.45
Compound 469  33.16
Compound 470  23.54
Compound 472  <3.00
Compound 473  <3.00
Compound 474  <3.00
Compound 475  <3.00
Compound 476  <3.00
Compound 477  <3.00
Compound 478  <3.00
Compound 479  <3.00
Compound 480  <3.00
Compound 481  12.10
Compound 482  <3.00
Compound 483  <3.00
Compound 484  <3.00
Compound 485  <3.00
Compound 486  <3.00
Compound 487  <3.00
Compound 488  <3.00
Compound 489  <3.00
Compound 490  <3.00
Compound 491  <3.00
Compound 492  <3.00
Compound 493  <3.00
Compound 494  2.07
Compound 495  0.35
Compound 496  0.64
Compound 497  0.51
Compound 498  0.60
Compound 499  0.98
Compound 500  0.35
Compound 501  23.13
Compound 502  15.68
Compound 503  10.35
Compound 504  18.93
Compound 505  1.21
Compound 506  19.5
Compound 507  1.86
Compound 508  0.48
Compound 509  13.59
Compound 510  1.48
Compound 511  2.16
Compound 512  28.30
Compound 513  15.96
Compound 514  2.15
Compound 515  1.90
Compound 516  2.13
Compound 517  1.71
Compound 518  1.52
Compound 519  1.72
Compound 521  1.24
Compound 522  1.09
Compound 551  0.47
Compound 552  2.63
Compound 553  2.80
Compound 554  1.46
Compound 555  <3.00
Compound 556  <3.00
Compound 557  <0.30
Compound 558  1.07
Compound 559  1.26
Compound 560  1.09
Compound 561  0.31
Compound 562  <1.00
Compound 563  <1.00
Compound 564  11.57
Compound 565  12.98
Compound 566  14.58
Compound 567  <1.00
Compound 568  4.32
Compound 569  <3.00
Compound 570  6.04
Compound 571  5.27
Compound 572  4.12
Compound 573  1.75
Compound 574  6.93
Compound 575  <3.00
Compound 576  <3.00
Compound 577  <3.00
Compound 578  <3.00
Compound 579  <3.00
Compound 580  <3.00
Compound 581  <3.00
Compound 582  <3.00
Compound 583  <3.00
Compound 584  <3.00
Compound 585  <3.00
Compound 586  <3.00
Compound 587  <3.00
Compound 588  9.33
Compound 589  <3.00
Compound 590  6.18
Compound 591  1.01
Compound 592  11.94
Compound 593  <3.00
Compound 594  3.60
Compound 595  3.87
Compound 596  5.47
Compound 597  1.47
Compound 598  53.04
Compound 599  <3.00
Compound 600  3.84
Compound 601  <3.00
Compound 602  3.98
Compound 603  <3.00
Compound 604  9.23
Compound 605  0.95
Compound 606  1.01
Compound 607  0.43
Compound 608  <0.30
Compound 609  <0.30
Compound 610  1.82
Compound 611  2.16
Compound 612  2.34
Compound 613  1.41
Compound 614  3.29
Compound 615  2.08
Compound 616  13.86
Compound 617  3.68
Compound 618  4.25
Compound 619  <3.00
Compound 620  3.58
Compound 621  <3.00
Compound 622  <3.00
Compound 623  <3.00
Compound 624  <3.00
Compound 625  <3.00
Compound 626  <3.00
Compound 627  <1.00
Compound 628  1.29
Compound 629  3.01
Compound 630  <1.00
Compound 631  <1.00
Compound 632  <1.00
Compound 633  1.19
Compound 634  1.74
Compound 635  1.56
Compound 636  3.89
Compound 637  <1.00
Compound 638  3.15
Compound 639  1.84
Compound 640  1.61
Compound 641  2.92
Compound 642  2.14
Compound 643  3.68
Compound 644  5.91
Compound 645  <3.00
Compound 646  1.77
Compound 647  5.62
Compound 648  2.04
Compound 649  2.69
Compound 650  0.95
Compound 651  262.90
Compound 652  0.72
Compound 653  1.10
Compound 654  2.03
Compound 655  1.58
Compound 656  2.98
Compound 657  2.63
Compound 658  <3.00
Compound 659  12.45
Compound 660  18.70
Compound 661  <10.00
Compound 662  3.20
Compound 663  136.67
Compound 664  15.08
Compound 666  31.23
Compound 667  30.49
Compound 668  9.13
Compound 669  15.29
Compound 671  <3.00
Compound 672  31.18
Compound 673  10.13
Compound 675  <3.00
Compound 676  <3.00
Compound 677  <3.00
Compound 678  <3.00
Compound 679  <3.00
Compound 680  4.04
Compound 681  25.90
Compound 682  12.50
Compound 683  <3.00
Compound 684  54.25
Compound 685  36.43
Compound 686  <3.00
Compound 687  <3.00
Compound 688  <3.00
Compound 689  <3.00
Compound 690  87.97
Compound 691  97.03
Compound 692  99.40
Compound 693  70.18
Compound 694  38.77
Compound 695  6.76
Compound 696  4.47
Compound 697  <3.00
Compound 698  <3.00
Compound 713  15.49
Compound 714  3.52
Compound 718  6.91
Compound 719  9.59
Compound 720  3.51
Compound 721  22.34
Compound 722  12.84
Compound 723  18.03
Compound 724  17.08
Compound 725  69.40
Compound 726  <3.00
Compound 728  20.33
Compound 729  27.33
Compound 730  15.66
Compound 731  19.18
Compound 732  29.35
Compound 733  <10.00
Compound 735  18.34
Compound 737  4.24
Compound 738  7.55
Compound 743  14.40
Compound 745  6.12
Compound 746  16.77
Compound 747  11.93
Compound 749  9.05
Compound 750  <3.00
Compound 751  13.11
Compound 752  <3.00
Compound 753  12.36
Compound 754  <3.00
Compound 756  10.33
Compound 757  18.84
Compound 763  11.18
Compound 764  5.92
Compound 765  6.88
Compound 768  10.62
Compound 769  4.44
Compound 770  16.49
Compound 786  1.33
Compound 787  1.69
Compound 788  2.04
Compound 789  1.16
Compound 790  4.32
Compound 791  5.50
Compound 792  1.26
Compound 793  1.41
Compound 794  0.97
Compound 795  1.92
Compound 796  0.35
Compound 797  3.39
Compound 798  3.62
Compound 799  3.72
Compound 800  9.24
Compound 801  4.70
Compound 802  1.20
Compound 803  4.92
Compound 804  1.23
Compound 805  4.76
Compound 806  3.90
Compound 807  <1.00
Compound 808  1.97
Compound 809  5.22
Compound 810  6.68
Compound 811  9.11
Compound 812  5.58
Compound 813  6.25
Compound 814  <3.00
Compound 815  16.74
Compound 816  14.77
Compound 817  36.14
Compound 818  7.38
Compound 819  5.95
Compound 820  17.86
Compound 821  17.86
Compound 822  5.90
Compound 823  6.93
Compound 824  3.22
Compound 825  4.52
Compound 826  4.44
Compound 827  3.50
Compound 828  9.33
Compound 829  3.91
Compound 830  4.81
Compound 831  3.88
Compound 832  4.97
Compound 833  7.89
Compound 834  19.02
Compound 835  6.46
Compound 836  0.77
Compound 837  12.91
Compound 838  <3.00
Compound 839  5.04
Compound 840  6.95
Compound 841  <3.00
Compound 842  3.22
Compound 843  4.19
Compound 844  <3.00
Compound 845  <3.00
Compound 846  <3.00
Compound 847  <3.00
Compound 848  2.20
Compound 849  <3.00
Compound 850  3.10
Compound 851  1.36
Compound 852  <1.00
Compound 853  2.14
Compound 854  1.33
Compound 855  1.75
Compound 856  1.77
Compound 857  1.18
Compound 858  0.46
Compound 859  0.39
Compound 860  0.65
Compound 861  0.52
Compound 862  0.35
Compound 863  1.22
Compound 864  0.74
Compound 865  1.49
Compound 866  1.92
Compound 867  2.24
Compound 868  <0.30
Compound 869  6.68
Compound 870  0.53
Compound 871  1.00
Compound 872  <3.00
Compound 873  0.66
Compound 874  <0.30
Compound 875  5.20
Compound 876  <3.00
Compound 877  <0.30
Compound 878  <0.30
Compound 879  3.72
Compound 880  0.08
Compound 881  0.18
Compound 882  0.33
Compound 883  0.04
Compound 884  0.95
Compound 885  1.24
Compound 886  0.81
Compound 887  1.75
Compound 888  2.55
Compound 889  0.33
Compound 890  3.91
Compound 891  1.47
Compound 892  14.84
Compound 893  <0.30
Compound 894  0.50
Compound 895  <0.30
Compound 896  <0.30
Compound 897  <0.30
Compound 898  <0.30
Compound 899  <1.00
Compound 900  <1.00
Compound 901  <1.00
Compound 902  <1.00
Compound 903  <1.00
Compound 904  1.71
Compound 905  1.18
Compound 906  1.83
Compound 907  6.75
Compound 908  13.16
Compound 909  1.02
Compound 910  7.81
Compound 911  <1.00
Compound 912  1.04
Compound 913  1.65
Compound 914  1.75
Compound 915  8.15
Compound 916  5.22
Compound 917  1.25
Compound 918  1.55
Compound 919  0.31
Compound 920  <1.00
Compound 921  1.22
Compound 922  2.89
Compound 923  18.79
Compound 924  40.16
Compound 925  25.50
Compound 926  <1.00
Compound 927  <1.00
Compound 928  <1.00
Compound 929  <1.00
Compound 935  0.17
Compound 936  5.59
Compound 937  137.00
Compound 938  1.41
Compound 939  <3.00
Compound 940  30.63
Compound 941  8.72
Compound 942  0.20
Compound 943  10.58
Compound 944  12.04
Compound 945  19.38
Compound 947  30.19
Compound 948  11.62
Compound 950  9.08
Compound 952  19.24
Compound 954  60.51
Compound 956  29.85
Compound 958  <1.00
Compound 959  <1.00
Compound 960  1.12
Compound 961  <1.00
Compound 962  <1.00
Compound 963  <1.00
Compound 965  27.22
Compound 966  16.04
Compound 967  6.57
Compound 969  <3.00
Compound 970  <3.00
Compound 971  <3.00
Compound 972  <3.00
Compound 973  <3.00
Compound 974  12.56
Compound 975  17.36
Compound 976  10.73
Compound 977  10.15
Compound 980  13.80
Compound 981  12.17
Compound 982  8.05
Compound 983  8.31
Compound 984  22.12
Compound 985  <3.00
Compound 986  28.95
Compound 987  <3.00
Compound 988  3.88
Compound 989  <3.00
Compound 990  <3.00
Compound 996  2.66
Compound 997  7.88
Compound 998  16.57
Compound 999  58.16
Compound 1001 <3.00
Compound 1002 2.58
Compound 1003 9.12
Compound 1006 6.31
Compound 1007 0.40
Compound 1008 0.30
Compound 1009 0.10
Compound 1010 0.24
Compound 1011 1.28
Compound 1012 1.89
Compound 1013 8.89
Compound 1015 11.07
Compound 1016 9.23
Compound 1017 0.87
Compound 1018 0.92
Compound 1019 0.41
Compound 1020 0.39
Compound 1021 5.57
Compound 1022 3.23
Compound 1023 0.99
Compound 1024 3.94
Compound 1025 5.71
Compound 1026 3.86
Compound 1027 1.20
Compound 1028 29.07
Compound 1029 34.73
Compound 1030 14.16
Compound 1033 18.66
Compound 1034 17.21
Compound 1035 3.70
Compound 1036 1.50
Compound 1037 38.51
Compound 1038 3.35
Compound 1039 2.76
Compound 1040 52.16
Compound 1041 10.25
Compound 1042 14.74
Compound 1043 8.26
Compound 1044 2.13
Compound 1045 13.11
Compound 1046 <1.00
Compound 1047 <1.00
Compound 1048 <1.00
Compound 1049 <1.00
Compound 1050 1.42
Compound 1051 1.16
Compound 1052 1.33
Compound 1053 <1.00
Compound 1054 <1.00
Compound 1055 1.96
Compound 1056 1.88
Compound 1057 1.26
Compound 1058 1.07
Compound 1059 0.43
Compound 1060 0.44
Compound 1061 1.99
Compound 1062 6.76
Compound 1064 <1.00
Compound 1065 1.21
Compound 1066 2.69
Compound 1067 2.79
Compound 1069 <1.00
Compound 1070 <1.00
Compound 1071 <1.00
Compound 1072 3.88
Compound 1073 20.36
Compound 1074 1.54
Compound 1075 1.34
Compound 1076 2.57

TABLE 5
Compound No.
              Inhibition (%) (300 μM)
Compound 2    77.30
Compound 131  32.40
Compound 230  50.42
Compound 231  32.76
Compound 232  44.92
Compound 233  33.62
Compound 234  37.88
Compound 235  47.92
Compound 236  49.42
Compound 237  33.12
Compound 238  30.58
Compound 239  59.08
Compound 240  37.92
Compound 241  46.94
Compound 242  37.61
Compound 243  50.17
Compound 244  30.72
Compound 245  31.68
Compound 246  32.62
Compound 247  34.81
Compound 248  30.30
Compound 249  41.59
Compound 250  37.86
Compound 251  31.22
Compound 357  65.82
Compound 366  69.87
Compound 471  50.99
Compound 523  50.09
Compound 524  42.75
Compound 525  38.89
Compound 526  40.24
Compound 527  40.94
Compound 528  58.38
Compound 529  80.96
Compound 530  38.16
Compound 531  35.68
Compound 532  76.00
Compound 533  36.87
Compound 534  43.82
Compound 535  52.98
Compound 536  88.25
Compound 537  82.05
Compound 538  30.31
Compound 539  88.39
Compound 540  38.41
Compound 541  32.16
Compound 542  41.11
Compound 543  30.2
Compound 544  60.05
Compound 545  88.81
Compound 546  85.19
Compound 547  66.61
Compound 548  85.72
Compound 549  85.10
Compound 550  78.88
Compound 665  82.34
Compound 670  70.17
Compound 674  85.12
Compound 699  58.35
Compound 700  40.28
Compound 701  53.98
Compound 702  49.17
Compound 703  57.92
Compound 704  46.62
Compound 705  44.68
Compound 706  47.79
Compound 707  41.22
Compound 708  42.04
Compound 709  59.36
Compound 710  83.13
Compound 711  81.04
Compound 712  48.73
Compound 715  84.11
Compound 716  85.77
Compound 717  53.54
Compound 727  67.74
Compound 734  64.91
Compound 736  61.49
Compound 739  58.89
Compound 740  58.55
Compound 741  50.93
Compound 742  77.57
Compound 744  83.71
Compound 748  56.45
Compound 755  67.27
Compound 758  58.21
Compound 759  63.85
Compound 760  73.34
Compound 761  46.24
Compound 762  52.08
Compound 766  81.89
Compound 767  81.83
Compound 771  85.12
Compound 772  67.72
Compound 773  53.91
Compound 774  58.85
Compound 775  44.62
Compound 776  49.19
Compound 777  34.17
Compound 778  39.12
Compound 779  51.64
Compound 780  47.74
Compound 781  51.18
Compound 782  86.76
Compound 783  88.84
Compound 784  88.49
Compound 785  39.53
Compound 930  40.20
Compound 931  31.22
Compound 932  36.09
Compound 933  37.62
Compound 934  39.27
Compound 946  45.00
Compound 949  72.60
Compound 951  68.51
Compound 953  67.80
Compound 955  57.67
Compound 957  54.91
Compound 964  67.50
Compound 968  52.70
Compound 978  74.08
Compound 979  73.73
Compound 991  30.11
Compound 992  31.92
Compound 993  39.71
Compound 995  42.10
Compound 1000 32.14
Compound 1004 34.20
Compound 1005 59.07
Compound 1014 55.20
Compound 1031 58.77
Compound 1032 39.98
Compound 1077 40.18
              Inhibition (%) (100 μM)
Compound 1063 63.94
Compound 1068 74.42

Pharmacological Test Example 2

Experiment of Sodium-Dependent Phosphate Uptake of Rabbit Jejunal Brush Border Membrane Vesicles

Jejunal epithelium was obtained from New Zealand white male rabbits (7 weeks old, obtained from KITAYAMA LABES Co., Ltd. (Japan)), and brush border membrane vesicles were isolated by the calcium precipitation method described in Kanako Katai et al., J. Biochem. 121, 50-55, 1997, and Peerce, B. E. et al., Biochemistry 26, 4272-4279, 1987. Thereafter, for compound 29 and compound 68, the phosphate uptake inhibitory activity was measured using the same samples with ³²P radioactive phosphorus (manufactured by Daiichi Kagaku Inc. (Japan)) by the rapid filtration method described in Kanako Katai et al., J. Biochem. 121, 50-55, 1997. As a result, these compounds had concentration-dependent inhibitory activity (FIG. 1). Further, in the same experiment, nonspective inhibitory activity against glucose absorption was determined using 14C-glucose (manufactured by Moravek Biochemical Inc. (US)). As a result, these compounds did not have the inhibitory activity (FIG. 2). In both the experiments, a group with the addition of potassium chloride was used as a negative control for nonspecific uptake. All the test results given below were expressed in terms of average value±standard error. Student's t-test was used for a significant test of the control group and the test compound group.

Pharmacological Test Example 3

Experiment of Sodium-Dependent Phosphate Uptake of Xenopus oocytes Which Expressed NaPi-2a

cDNA of human NaPi-2a described in Magagnin S. et al., Proc Natl Aca Sci USA, 90 (13): 5979-5983, 1993 was cloned by PCR. In the same manner as in Pharmacological Test Example 1, NaPi-2a was expressed in Xenopus oocytes, and the phosphate uptake inhibitory activity was measured with ³²P radioactive phosphorus. As a result, compound 1 had concentration-dependent inhibitory activity against NaPi-2a (FIG. 3). Compound 29 had inhibitory activity against not only NaPi-2b but also NaPi-2a (FIG. 4). In the test, a group with the addition of choline chloride (Choline Cl) was used as a negative control for nonspecific uptake, and PFA (phosphonoformic acid) was used as a positive control for phosphate transport inhibition.

Further, the compounds according to the present invention had inhibitory activity with IC₅₀ values shown in Table 6. IC₅₀ values were determined by determining an inhibition curve by an approximation formula using the least square from inhibitory activity values obtained from five concentration levels of the compound and determining the concentration of the compound which exhibits 50% of the maximum inhibitory activity.

TABLE 6
IC50 (μM)
Compound 260  <3.00
Compound 262  4.42
Compound 264  4.36
Compound 591  4.04
Compound 592  9.51
Compound 627  3.53
Compound 628  3.59
Compound 629  12.94
Compound 630  3.50
Compound 631  2.43
Compound 632  28.66
Compound 633  13.46
Compound 634  16.87
Compound 635  1.34
Compound 636  5.30
Compound 637  0.95
Compound 638  4.22
Compound 639  11.15
Compound 640  15.59
Compound 641  7.53
Compound 642  13.30
Compound 786  <3.00
Compound 787  <3.00
Compound 788  6.64
Compound 789  9.28
Compound 791  6.70
Compound 793  8.46
Compound 794  9.57
Compound 795  8.52
Compound 800  10.05
Compound 801  3.72
Compound 802  5.96
Compound 806  12.14
Compound 807  9.07
Compound 810  23.81
Compound 811  37.22
Compound 813  35.59
Compound 814  18.34
Compound 818  31.43
Compound 822  18.01
Compound 824  8.19
Compound 827  24.37
Compound 828  10.02
Compound 829  <3.00
Compound 830  10.73
Compound 831  28.83
Compound 832  6.40
Compound 833  38.11
Compound 834  52.10
Compound 835  10.98
Compound 836  10.18
Compound 838  10.17
Compound 839  23.15
Compound 840  34.06
Compound 841  19.85
Compound 845  <3.00
Compound 846  <3.00
Compound 858  <1.00
Compound 859  1.60
Compound 860  <1.00
Compound 861  <1.00
Compound 862  1.65
Compound 863  6.90
Compound 864  1.94
Compound 865  4.34
Compound 878  7.22
Compound 880  1.30
Compound 881  2.67
Compound 882  4.45
Compound 883  1.98
Compound 884  35.90
Compound 886  2.93
Compound 887  15.06
Compound 889  1.41
Compound 890  1.33
Compound 891  13.86
Compound 893  5.11
Compound 894  3.61
Compound 895  5.52
Compound 896  7.40
Compound 899  <1.00
Compound 900  2.53
Compound 901  <1.00
Compound 902  <1.00
Compound 903  <1.00
Compound 904  1.69
Compound 914  3.13
Compound 935  9.68
Compound 936  30.05
Compound 985  <3.00
Compound 987  16.31
Compound 989  7.84
Compound 990  7.14
Compound 1007 1.00
Compound 1008 2.30
Compound 1009 1.41
Compound 1020 2.25
Compound 1027 1.58

Pharmacological Test Example 4

Inhibitory Activity Against ³²P Absorption from Intestinal Tract

SD rats (6 to 7 weeks old, obtained from Charles River Japan, Inc. (Japan)) were raised with low-phosphorus diet (phosphorus content 0.1%, manufactured by Oriental Yeast Co., Ltd. (Japan)) for 3 to 4 days and then fasted for about 24 hr for experiment. ³²P was diluted with purified water or liquid feed (CLEA JAPAN INC. (Japan)) to 0.7 to 3.5 MBq/ml and was forcibly orally administered at a dose of 5 ml/kg (administered into the gaster through an oral probe). The compounds or media were forcibly orally administered at a dose of 5 ml/kg (divided dose of twice), 30 min before the administration of ³²P and simultaneously with the administration of ³²P. Blood was collected from caudal artery 30 min, 45 min, or 60 min after ³²P administration, and blood ³²P radioactivity was measured with a liquid scintillation counter. Inhibition of an increase in blood radioactivity was used as a measure of inhibition of phosphate absorption from the intestinal tract.

The results are expressed in terms of the percentage inhibition determined by the following equation. (Blood radioactivity for group with the administration of medium−Blood radioactivity for group with the administration of compound)/(Blood radioactivity for group with the administration of medium)×100

t-Test was used for a significant test of the average value difference of blood radioactivity.

The results are shown in Table 7. As is apparent from the table, the compounds significantly inhibited phosphate absorption from the intestinal tract.

TABLE 7
Inhibitory activity against 32P absorption from intestinal tract
		Blood radioactivity
Compound	Dose, mg/kg	inhibition, %
91	320	28.3
92	160	25.5
88	400	29.1
163	360	57.8
130	270	22.8
157	320	20.7
164	400	55.0
165	400	27.6
252	400	29.2
253	400	39.0
254	400	68.4
315	100	42.4
372	100	63.7
285	80	60.3

For all the compounds, a significant difference was observed as compared with the group with the administration of medium at p<0.05.

Claims

1. A compound represented by formula (I) or a pharmaceutically acceptable salt or solvate thereof:

2. The compound according to claim 1, wherein A represents a five- to nine-membered unsaturated carbocyclic moiety or a five- to nine,-membered unsaturated heterocyclic moiety, and represents a double bond, the carbocyclic moiety and heterocyclic moiety represented by A are optionally substituted by (a) a halogen atom; (b) hydroxyl; (c) C1-5 alkyl; (d) C1-5 alkoxy; (e) aryl; (f) aryloxy; (g) arylthio; (h) alkylthio; (i) nitro; or (j) amino, (c) the C1-6 alkyl group, (d) the C1-5 alkoxy group, (e) the aryl group, (f) the aryloxy group, (g) the arylthio group, and (h) the alkylthio group are optionally substituted by (1) hydroxyl, (2) thiol, (3) amino, (4) C1-6 alkoxy, (5) C1-6 alkylthio, (6) C1-6 alkylsulfonyl, (7) mono- or di-C1-6 alkylamino in which the di-C1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms, (8) aryloxy, (9) arylthio, (10) arylsulfonyl, (11) aryl, (12) a heterocyclic group, (13) a halogen atom, or (14) arylamino in which the amino group is optionally substituted by C1-6 alkyl, and the aryl group is optionally substituted by a halogen atom, C1-6 alkyl, C1-6 alkoxy, or C1-6 alkylamino, when the carbocyclic moiety and the heterocyclic moiety are substituted by two (c) C1-6 alkyl groups, they together may form a C3-5 alkylene chain, R5 represents C1-6 alkyl, aryl, C1-6 alkoxy, aryloxy, C1-6 alkylamino, arylamino, C1-6 alkylthio, arylthio, C3-7 cycloalkyl, or a heterocyclic group, and the C1-6 alkyl, aryl, C1-6 alkoxy, aryloxy, C1-6 alkylamino, arylamino, C1-6 alkylthio, arylthio, C3-7 cycloalkyl, or heterocyclic group represented by R5 may be the same or different, and is optionally substituted by (I) a halogen atom; (II) C1-6 alkyl optionally containing a substituent selected from the group consisting of (1) hydroxyl, (2) thiol, (3) amino, (4) C1-6 alkoxy, (5) C1-6 alkylthio, (6) C1-6 alkylsulfinyl, (7) C1-6 alkylsulfonyl, (8) mono- or di C1-6 alkylamino, (8′) amino substituted by a heterocyclic group optionally substituted by C1-6 alkyl, (9) C1-6 alkylcarbonyloxy (10) C1-6 alkylcarbonylthio, (11) C1-6 alkylcarbonylamino, (12) aryloxy, (13) arylthio, (14) arylsulfinyl, (15) arylsulfonyl, (16) arylamino, (17) C1-6 alkyl- or aryl-sulfonylamino, (18) C1-6, alkyl- or aryl-ureido, (19) C1-6 alkoxy- or aryloxy-carbonylamino, (20) C1-6 alkylamino- or arylamino-carbonyloxy, (21) carboxyl, (22) nitro, (23) a heterocyclic group, (23′) Het-S(═O)j- wherein Het represents a heterocyclic group, j is 0, 1, or 2, and Het is optionally substituted by alkyl optionally substituted by mono- or di-C1-6 alkylamino in which the di-C1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms and one or two alkyl groups on the amino group and the cyclic amino moiety are optionally substituted by hydroxyl, (24) cyano, and (25) a halogen atom, wherein the alkyl moiety in (4) the C1-6 alkoxy group, (5) the C1-6 alkylthio group, (6) the C1-6, alkylsulfinyl group, and (7) the C1-6 alkylsulfonyl group is optionally substituted by a halogen atom; C1-6 alkyl; C, 6, alkoxy; C1-6 alkylthio; mono- or dl-C1-6 alkylamino in which the di-C1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms; aryloxy; arylthio; hydroxyl; carboxyl; —S(═O)2(—OH); C1-6 alkoxy- or aryloxy-carbonyl; C1-6 alkylcarbonyl; aryl; or a heterocyclic group optionally substituted by alkyl optionally substituted by mono- or di-C1-6 alkylamino in which the di-C1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms, and one or two alkyl groups on the amino group and the cyclic amino moiety are optionally substituted by hydroxy, and in (8) the mono- or di-C1-6 alkylamino group, the di-C1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms, and one or two alkyl groups on the amino group and the cyclic amino moiety are optionally substituted by a halogen atom; C1-6 alkyl optionally substituted by hydroxyl; C1-6 alkoxy; C1-6 alkylthio; mono- or di-C1-6 alkylamino in which one or two alkyl groups on the amino group are optionally substituted by hydroxyl; arylamino in which the amino group is optionally substituted by C1-6 alkyl; mono- or di-C1-6 alkylcarbamoylmethyl in which the di-C1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms, and one or two alkyl groups on the amino group and the cyclic amino moiety are optionally substituted by hydroxyl; aryloxy; arylthio; an oxygen atom (═O)— hydroxyl; carboxyl; C1-6 alkoxy- or aryloxy-carbonyl; C1-6 alkylcarbonyl; aryl optionally substituted by a halogen atom or hydroxyl; or a heterocyclic group; (III) C1-6 alkoxy optionally substituted by a halogen atom; (IV) C1-6 alkylthio optionally substituted by a halogen atom; (V) C3-7 cycloalkyl; (VI) aryl; (VII) aryloxy; (VIII) C1-6 alkylcarbonylamino; (VIX) C1-6 alkylcarbonyloxy; (X) hydroxyl; (XI) nitro; (XII) cyano; (XIII) amino; (XIV) mono- or di-C1-6 alkylamino in which the di-C1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms; (XV) arylamino; (XVI) C1-6 alkyl- or aryl-sulfonylamino; (XVII) C1-6 alkyl- or aryl-ureido; (XVIII) C1-6 alkoxy- or aryloxy-carbonylamino; (XIX) C1-6 alkylamino- or arylamino-carbonyloxy; (XX) C1-6 alkoxy- or aryloxy-carbonyl; (XXI) acyl; (XXII) carboxyl; (XXIII) carbamoyl; (XXIV) mono- or di-alkylcarbamoyl; (XXV) a heterocyclic group; (XXVI) alkyl- or aryl-sulfonyl; (XXVII) C2-6 alkenyloxy; or (XXVIII) C2-6 alkenyloxy, Z represents group A or group B wherein R6, R7, and R17 are as defined in claim 1, R101 and R102 together represent ═O, and R103 and R104 represent a hydrogen atom, or R101 and R104 together represent a bond, and R102 and R103 together represent a bond.

3. The compound according to claim 1, wherein A represents formula (IIa) or formula (IIa′):

4. The compound according to claim 1, wherein A represents formula (IIa):

5. The compound according to claim 3, wherein R1, R3, and R4, which may be the same or different, represent a hydrogen atom; a halogen atom; C1-6 alkyl in which the alkyl group is optionally substituted by C1-6 alkoxy or a halogen atom; aryl optionally substituted by C1-6 alkoxy or a halogen atom; C1-6 alkoxy in which the alkoxy group is optionally substituted by C1-6 alkoxy or a halogen atom; or aryloxy optionally substituted by C1-6 alkoxy or a halogen atom, R2 represents a hydrogen atom; a halogen atom; hydroxyl; C1-6 alkyl in which the alkyl group is optionally substituted by (1) hydroxyl, (2) thiol, (3) amino, (4) C1-6 alkoxy, (5) C1-6 alkylthio, (6) C1-6 alkylsulfonyl, (7) mono- or di-C1-6 alkylamino in which the di-C1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms, (8) aryloxy, (9) arylthio, (10) arylsulfonyl, (11) aryl, (12) a heterocyclic group, (13) a halogen atom, or (14) arylamino in which the amino group is optionally substituted by C1-6 alkyl, and the aryl group is optionally substituted by a halogen atom, C1-6 alkyl, C1-6 alkoxy, or C1-6 alkylamino; or C1-6 alkoxy in which the alkoxy group is optionally substituted by (1) hydroxyl, (2) thiol, (3) amino, (4) C1-6 alkoxy, (5) C1-6 alkylthio, (6) C1-6 alkylsulfonyl, (7) mono- or di-C1-6 alkylamino in which di-C1-6 alkylamino may form cyclic amino optionally containing 1 to 3 heteroatoms, (8) aryloxy, (9) arylthio, (10) arylsulfonyl, (11) aryl, (12) a heterocyclic group, or (13) a halogen atom.

6. The compound according to claim 3, wherein R1, R2, R3 and R4, which may be the same or different, represent a hydrogen atom; a halogen atom; hydroxyl; optionally substituted C1-6 alkyl; optionally substituted C1-6 alkenyl; optionally substituted C1-6 alkoxy; optionally substituted mono- or di-arylamino; optionally substituted mono- or di-C1-6 alkylamino in which the dialkylamino together may form optionally substituted cyclic amino optionally containing 1 to 3 heteroatoms; optionally substituted mono- or di-C2-6 alkenylamino in which the di-C2-6 alkenylamino group together may form optionally substituted unsaturated cyclic amino optionally containing 1 to 3 heteroatoms, and, when R2 and R3 are optionally substituted C1-6 alkyl or optionally substituted C2-6 alkenyl, the alkyl or alkenyl groups together with the carbon atoms to which they are respectively attached may form an unsaturated five- to seven-membered carbocyclic ring.

7. The compound according to claim 3, wherein R1, R2, R3, and R4, which may be the same or different, represent a hydrogen atom; a halogen atom; hydroxyl; optionally substituted C1-6 alkyl; or optionally substituted C1-6 alkoxy.

8. The compound according to claim 3, wherein R1, R2, R3, and R4 represent a hydrogen atom.

9. The compound according to claim 3 wherein R1 and R4 represent a hydrogen atom, any one of R2 and R3 represents a halogen atom; hydroxyl; optionally substituted C1-6 alkyl; optionally substituted C1-6 alkoxy; optionally substituted mono- or di-arylamino; optionally substituted mono- or di-C1-6 alkylamino in which the dialkylamino together may form optionally substituted cyclic amino optionally containing 1 to 3 heteroatoms; optionally substituted mono- or di-C2-6 alkenylamino in which the di-C2-6 alkenylamino group together may form optionally substituted unsaturated cyclic amino, wherein the cyclic amino groups may contain 1 to 3 heteroatoms, and the other represents a hydrogen atom.

10. The compound according to claim 3, wherein R1 and R4 represent a hydrogen atom, and any one of R2 and R3 represents a halogen atom; hydroxyl; optionally substituted C1-6 alkyl; optionally substituted C1-6 alkoxy, and the other represents a hydrogen atom.

11. The compound according to claim 3, wherein R1 and R4 represent a hydrogen atom, and R2 and R3, which may be the same or different, represent a halogen atom; hydroxyl; optionally substituted C1-6 alkyl; or optionally substituted C1-6 alkoxy.

12. The compound according to claim 3, wherein R1 and R4 represent a hydrogen atom, and R2 and R3 together with the carbon atoms to which they are respectively attached form an unsaturated five- to seven-membered carbocyclic ring.

13. The compound according to claim 3, wherein R1 and R4 represent a hydrogen atom, and R2 and R3, which may be the same or different, represent optionally substituted C1-6 alkoxy.

14. The compound according to claim 3, wherein R1 and R4 represent a hydrogen atom, any one of R2 and R3 represents optionally substituted mono- or di-C1-6 alkylamino in which the di-C1-6 alkylamino may form cyclic amino optionally containing 1 to 3 heteroatoms, and the other represents a hydrogen atom.

15. The compound according to claim 3, wherein R1 and R4 represent a hydrogen atom, any one of R2 and R3 represent optionally substituted C1-6 alkoxy, and the other represents a hydrogen atom.

16. The compound according to claim 6, wherein R1 and R4 represent a hydrogen atom.

17. The compound according to claim 1, wherein A represents formula (11b), (11c), or (11d):

18. The compound according to claim 1, wherein A represents formula (11b) or (IIc):

19. The compound according to claim 17, wherein A represents formula (11b), (i) R31 and R32 represent a hydrogen atom, (ii) any one of R31 and R32 represents a hydrogen atom, and the other represents C1-6 alkyl optionally substituted by mono- or di-C1-6 alkylamino, which may form cyclic amino, or a halogen atom, and the cyclic amino group may contain 1 to 3 heteroatoms, (iii) R31 and R32, which may be the same or different, represent C1-6 alkyl optionally substituted by mono- or di-C1-6 alkylamino, which may form cyclic amino, or a halogen atom, and the cyclic amino group may contain 1 to 3 heteroatoms, or (iv) R31 and R32 together with the carbon atoms to which they are respectively attached form an unsaturated five- to seven-membered carbocyclic ring.

20. The compound according to claim 17, wherein A represents formula (IIb), R31 and R32 represent a hydrogen atom, or any one of R31 and R32 represents a hydrogen atom with the other representing C1-6 alkyl optionally substituted by a halogen atom, or R31 and R32 together with the carbon atoms to which they are respectively attached form an unsaturated five- to seven-membered carbocyclic ring.

21. The compound according to claim 17, wherein A represents formula (IIc), (i) R33 and R34 represent a hydrogen atom, (ii) any one of R33 and R34 represents a hydrogen atom, and the other represents C1-6 alkyl optionally substituted by mono- or di-C1-6 alkylamino, which may form cyclic amino, or a halogen atom, and the cyclic amino group may contain 1 to 3 heteroatoms, (iii) R33 and R34, which may be: the same or different, represent C1-6, alkyl optionally substituted by mono- or di-C1-6 alkylamino, which may form cyclic amino, or a halogen atom, and the cyclic amino group may contain 1 to 3 heteroatoms, or (iv) R33 and R34 together with the carbon atoms to which they are respectively attached form an unsaturated five- to seven-membered carbocyclic ring.

22. The compound according to claim 17, wherein A represents formula (IIc), R33 and R34 represent a hydrogen atom, or any one of R33 and R34 represents a hydrogen atom with the other representing C1-6 alkyl optionally substituted by a halogen atom, or R33 and R34 together with the carbon atoms to which they are respectively attached form an unsaturated five- to seven-membered carbocyclic ring.

23. The compound according to claim 17, wherein A represents formula (IId), R35 and R36 represent a hydrogen atom, or any one of R35 and R36 represents a hydrogen atom with the other representing C1-6 alkyl optionally substituted by a halogen atom.

24. The compound according to claim 1, wherein R5 represents optionally substituted C5-7 cycloalkyl, optionally substituted aryl, an optionally substituted saturated or unsaturated five- or six membered heterocyclic group, or an optionally substituted saturated or unsaturated nine- to eleven-membered bicyclic heterocyclic group.

25. The compound according to claim 24, wherein the aryl group is phenyl or naphthyl.

26. The compound according to claim 24, wherein the heterocyclic group is selected from pyridyl, furyl, thienyl, isoxazole, pyrimidyl, and quinoxalinyl.

27. The compound according to claim 1, wherein R5 represents a cyclic group selected from C5-7 cycloalkyl, phenyl, pyridyl, furyl, thienyl, isoxazole, pyrimidyl, and quinoxalinyl, in which the cyclic group is optionally substituted by a halogen atom; C1-6 alkyl optionally substituted by a halogen atom; C1-6 alkoxy optionally substituted by a halogen atom; or hydroxyl.

28. The compound according to claim 1, wherein R5 represents a cyclic group selected from C5-7 cycloalkyl, phenyl, pyridyl, furyl, thienyl, isoxazole, pyrimidyl, and quinoxalinyl, in which the cyclic group is optionally substituted by C1-6 alkyl optionally substituted by optionally substituted C1-6 alkoxy, optionally substituted C1-6 alkylthio, optionally substituted C1-6 alkylsulfinyl, optionally substituted C1-6 alkylsulfonyl, or optionally substituted mono- or di-C1-6 alkylamino in which the di-C1-6 alkylamino may form cyclic amino optionally containing 1 to 3 heteroatoms.

29. The compound according to claim 1, wherein R5 represents a group of formula (IIIa), (IIIb), or (IIIc);

30. The compound according to claim 29, wherein R8, R9, R10, R11, and R12, which may be the same or different, represent a hydrogen atom; a halogen atom; hydroxymethyl; C1-6 alkyl optionally substituted by a halogen atom; or C1-6 alkoxy optionally substituted by a halogen atom.

31. The compound according to claim 27, wherein substituted C1-6 alkyl which may be represented by R8, R9, R10, R11, and R12 represents a group of formula (IV) —CH2-Q-X1-R13  (IV) wherein Q represents an oxygen atom, a sulfur atom, sulfinyl, or sulfonyl, X1 represents a bond or straight chain or branched chain alkylene having 1 to b carbon atoms, R13 represents a hydrogen atom, a halogen atom, C1-6, alkyl, C1-6 alkoxy, C1-6 alkylthio, mono- or di-C1-6 alkylamino in which the di-C1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms, aryloxy, arylthio, hydroxyl, carboxyl, —S(═O)2(—OH), C1-6 alkoxy- or aryloxy-carbonyl, C1-6 alkylcarbonyl, aryl, or a heterocyclic group optionally substituted by alkyl optionally substituted by mono- or di-C1-6 alkylamino in which the di-C1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms, and one or two alkyl groups on the amino group and the cyclic amino moiety are optionally substituted by hydroxyl; or a group of formula (V) wherein X2 represents a bond or straight chain or branched chain alkylene having 1 to 5 carbon atoms, X3 represents a bond or straight chain or branched chain alkylene having 1 to 5 carbon atoms, R14 and R15, which may be the same or different, represent a hydrogen atom; a halogen atom; C1-6 alkyl optionally substituted by hydroxyl, a halogen atom, aryl optionally substituted by a halogen atom, C1-6 alkyl, or C1-6 alkyloxy, a heterocyclic group optionally substituted by a halogen atom, C1-6 alkyl, or C1-6, alkyloxy, and, when one or two alkyl groups on the amino group and the cyclic amino moiety are substituted by two C1-6 alkyl groups, they together may form C3-7 cycloalkyl; C1-6 alkoxy; C1-6 alkylthio; mono- or di-C1-6 alkylamino in which the di-C1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms, and one or two alkyl groups on the amino group and the cyclic amino moiety are optionally substituted by hydroxyl; arylamino in which the amino group is optionally substituted by C1-6 alkyl; mono- or di-C1-6 alkylcarbamoylmethyl in which the di-C1-6 alkylamino may form cyclic amino optionally containing 1 to 3 heteroatoms, and one or two alkyl groups on the amino group and the cyclic amino moiety are optionally substituted by hydroxyl; aryloxy; arylthio; an oxygen atom (═O); hydroxyl; carboxyl; C1-6 alkoxy- or aryloxy-carbonyl; C1-6 alkylcarbonyl; aryl optionally substituted by a halogen atom or hydroxyl; or a heterocyclic group, provided that, when X2 represents a bond, R14 represents a hydrogen atom, or when X3 represents a bond, R15 represents a hydrogen atom, or R14 and R15 together with a nitrogen atom to which they are respectively attached to may form a heterocyclic group that may contain 1 to 3 heteroatoms in addition to the nitrogen atom, to which R14 and R15 are attached, and is optionally substituted by hydroxyl; C1-6 alkyl optionally substituted by hydroxyl, a halogen atom, aryl optionally substituted by a halogen atom, C1-6 alkyl, or C1-6 alkyloxy, or a heterocyclic group optionally substituted by a halogen atom, C1-6 alkyl, or C1-6 alkyloxy, and, when one or two alkyl groups on the amino group and the cyclic amino moiety are substituted by two C1-6 alkyl groups, they together may form C3-7 cycloalkyl, mono- or di-C1-6 alkylamino in which the di-C1-6 alkylamino may form cyclic amino optionally containing 1 to 3 heteroatoms, and one or two alkyl groups on the amino group and the cyclic amino moiety are optionally substituted by hydroxyl; a saturated or unsaturated five or six-membered heterocyclic group; mono- or di-C1-6 alkylcarbamoylmethyl in which the di-C1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms, and one or two alkyl groups on the amino group and the cyclic amino moiety are optionally substituted by hydroxyl; phenyl; or an oxygen atom (═O), and, when one carbon atom in the cyclic amino moiety is substituted by two C1-6 alkoxy groups which may be the same or different, the two alkoxy groups together may form group —O—(CH2)p-O— wherein p is an integer of 2 to 4, and the cyclic amino group may condense with a monocyclic or bicyclic aromatic carbocyclic ring or a monocyclic or bicyclic aromatic heterocyclic ring to represent a bicyclic or tricyclic heterocyclic group.

32. The compound according to claim 29, wherein D, E, J, L, and M represent a carbon atom.

33. The compound according to claim 29, wherein any one or two of D, E, J, L, and M represent a nitrogen atom and the others represent a carbon atom.

34. The compound according to claim 29, wherein R5 represents formula (IIIa), and D, E, J, L, and M represent a carbon atom.

35. The compound according to claim 29, wherein R5 represents formula (IIIa), and any one or two of D, E, J, L, and M represent a nitrogen atom with the others representing a carbon atom.

36. The compound according to claim 29, wherein R5 represents formula (IIIb), D, E, and J represent a carbon atom, and G represents an oxygen or sulfur atom.

37. The compound according to claim 29, wherein R5 represents formula (IIIc), D, E, and J represent a carbon atom, and G represents an oxygen or sulfur atom.

38. The compound according to claim 29, wherein R5 represents formula (IIIa), D, E, J, L, and M represent a carbon atom, any one or two of R8, R9, R10, R11, and R12, which may be the same or different, represent a halogen atom; hydroxymethyl; C1-6 alkyl optionally substituted by a halogen atom; or C1-6 alkoxy optionally substituted by a halogen atom, and the others represent a hydrogen atom.

39. The compound according to claim 29, wherein R5 represents formula (IIIa), any one or two of D, E, J, L, and M represent a nitrogen atom, and the others represent a carbon atom, any one or two of R8, R9, R10, R11, and R12, which may be the same or different, represent a halogen atom; hydroxymethyl; C1-6 alkyl optionally substituted by a halogen atom, or C1-6 alkoxy optionally substituted by a halogen atom, and the others represent a hydrogen atom.

40. The compound according to claim 29, wherein R5 represents formula (IIIb), D, E, and J represent a carbon atom, and G represents an oxygen or sulfur atom, one or two of R8, R9, and R10, which may be the same or different, represent a halogen atom; hydroxymethyl; C1-6 alkyl optionally substituted by a halogen atom; or C1-6 alkoxy optionally substituted by a halogen atom, and the others represent s hydrogen atom.

41. The compound according to claim 29, wherein R5 represents formula (IIIc), D, E, and J represent a carbon atom, and G represents an oxygen or sulfur atom, one or two of R8, R9, and R10, which may be the same or different, represent a halogen atom; hydroxymethyl; C1-6 alkyl optionally substituted by a halogen atom; or C1-6 alkoxy optionally substituted by a halogen atom, and the others represent a hydrogen atom.

42. The compound according to claim 29, wherein R5 represents formula (IIIa), D, E, J, L, and M represent a carbon atom, R8, R9, and R12 represent a hydrogen atom, one of R10 and R11 represents a group of formula (IV) —CH2-Q-X1-R13  (IV) wherein Q, X1, and R13 are as defined in claim 31, or a group of formula (V) wherein X2, X3, R14, and R15 are as defined in claim 31, and the other group represents a hydrogen atom.

43. The compound according to claim 29, wherein R5 represents formula (IIIa), any one or two of D, E, J, L, and M represent a nitrogen atom, and the others represent a carbon atom, R8, R9, and R12 represent a hydrogen atom, one of R10 and R11 represents a group of formula (IV) —CH2-Q-X1=R13  (IV) wherein Q, X1, and R13 are as defined in claim 31, or a group of formula (V) wherein X2, X3, R4, and R15 are as defined in claim 31, and the other group represents a hydrogen atom.

44. The compound according to claim 29, wherein R5 represents formula (IIIb), D, E, and J represent a carbon atom, and G represents an oxygen or sulfur atom, one of R8, R9, and R10 represents a group of formula (IV) —CH2-Q-X1-R13  (IV) wherein Q, X1, and R13 are as defined in claim 31, or a group of formula (V) wherein X2, X3, R14, and R15 are as defined in claim 31, and the other groups represent a hydrogen atom.

45. The compound according to claim 29, wherein R5 represents formula (IIIc), D, E, and J represent a carbon atom, and G represents an oxygen or sulfur atom, one of R8, R9, and R10 represents a group of formula (IV) —CH2-Q-X1-R13  (IV) wherein Q, X1, and R13 are as defined in claim 31, or a group of formula (V) wherein X2, X3, R14, and R15 are as defined in claim 31, and the other groups represent a hydrogen atom.

46. The compound according to claim 1, wherein R6 represents a hydrogen atom; optionally substituted C1-6 alkyl; or optionally substituted aryl, R7 represents optionally substituted aryl, optionally substituted aryl C1-6 alky, optionally substituted aryl C2-6 alkenyl, or optionally substituted saturated or unsaturated five- or six-membered heterocyclic group.

47. The compound according to claim 46, wherein R6 represents a hydrogen atom; C1-6 alkyl optionally substituted by a halogen atom or C1-6 alkoxy; or aryl optionally substituted by a halogen atom, C1-6 alkyl, or C1-6 alkoxy.

48. The compound according to claim 46, wherein R6 represents a hydrogen atom or C1-6 alkyl.

49. The compound according to claim 46, wherein R7 represents a cyclic group selected from phenyl, naphthyl, furyl, pyrrolyl, and thienyl and is optionally substituted by a halogen atom; C1-6 alkyl optionally substituted by a halogen atom; C1-6 alkoxy in which the alkoxy group is optionally substituted by a halogen atom, aryloxy optionally substituted by a halogen atom and C1-6 alkyl, C1-6 alkoxy in which the alkoxy group is optionally substituted by mono- or di-C1-6 alkylamine in which the di-C1-6 alkylamino group may form cyclic amino optionally containing 1 to 3 heteroatoms, or by a halogen atom, arylthio optionally substituted by a halogen atom and C1-6 alkyl, C1-6 alkylthio in which the alkylthio group is optionally substituted by mono- or di-C1-6 alkylamine in which the di-C1-6 alkylamino may form cyclic amino optionally containing 1 to 3 heteroatoms, or by a halogen atom, arylamino optionally substituted by C1-6 alkyl, mono- or di-C1-6 alkylamine in which the di-C1-6 alkylamino may form cyclic amino optionally containing 1 to 3 heteroatoms; hydroxyl; mono- or di-C1-6 alkylamino in which the di-C1-6 alkylamino may form cyclic amino optionally containing 1 to 3 heteroatoms; nitro; C2-6 alkenyloxy; or C2-6 alkynyloxy.

50. The compound according to claim 1, wherein formula (I) is represented by formula (I-1)

51. The compound according to claim 50, wherein A represents formula (IIa) or formula (IIa′):

52. The compound according to claim 50, wherein A represents formula (IIa):

53. The compound according to claim 50, wherein A represents formula (IIb):

54. The compound according to claim 50, wherein A represents formula (IIc):

55. The compound according to claim 50, wherein A represents formula (IId):

56. The compound according to claim 51, wherein R5 represents formula (IIIa), formula (IIIb), or formula (IIIc)

57. The compound according to claim 50, wherein A represents formula (IIa) or formula (IIa′):

58. The compound according to claim 50, wherein A represents formula (IIa) or formula (IIa′)

59. The compound according to claim 50, wherein A represents formula (IIb)

60. The compound according to claim 50, wherein A represents formula (IIb)

61. The compound according to claim 50, wherein A represents formula (IIc)

62. The compound according to claim 50, wherein A represents formula (IIc)

63. The compound according to claim 50, wherein A represents formula (IId)

64. The compound according to claim 50, wherein A represents formula (IId)

65. A compound represented by formula (I-3) or a pharmaceutically acceptable salt or solvate thereof:

66. A pharmaceutical composition comprising as an active ingredient a compound according to claim 1 or a pharmaceutically acceptable salt or solvate thereof.

67-86. (canceled)

87. A method for preventing or treating a disease for which serum phosphorus lowering action or phosphate transport inhibition is therapeutically effective, said method comprising the step of administering a therapeutically or prophylactically effective amount of a compound according to claim 1 or a pharmaceutically acceptable salt or solvate thereof to a mammal.

88. The method according to claim 87, wherein the disease for which serum phosphorus lowering action or phosphate transport inhibition is therapeutically or prophylactically effective is hyperphosphatemia.

89. The method according to claim 87, wherein the disease for which serum phosphorus lowering action or phosphate transport inhibition is therapeutically or prophylactically effective is renal failure or chronic renal failure.

90. The method according to claim 87, wherein the diseases for which serum phosphorus lowering action or phosphate transport inhibition is therapeutically or prophylactically effective are secondary hyperparathyroidism and primary hyperparathyroidism and diseases related thereto.

91. The method according to claim 90, wherein the secondary hyperparathyroidism-related disease is renal osteodystrophy, central or peripheral nervous system damage induced by PTH increase or vitamin D lowering, anemia, myocardiopathy, hyperlipidemia, anomaly of saccharometabolism, pruritus cutaneus, tendon rupture, sexual dysfunction, muscle damage, skin ischemic ulcer, growth retardation, heart conduction disturbance, pulmonary diffusing impairment, immune deficiency, ostealgia and arthralgia, bone deformity, or fracture.

92. The method according to claim 87, wherein the disease for which serum phosphorus lowering action or phosphate transport inhibition is therapeutically or prophylactically effective is calcium/phosphorus metabolic disorder, for example, metabolic osteopathy.

93. The method according to claim 87, wherein the disease for which serum phosphorus lowering action or phosphate transport inhibition is therapeutically or prophylactically effective is a disease for which the suppression of calcium and/or phosphorus product is therapeutically effective.

94. The method according to claim 93, wherein the disease for which the suppression of calcium and/or phosphorus product is therapeutically effective is calcification of cardiovascular system in dialysis patients, age-related arterial sclerosis, diabetic vasculopathy, calcification of soft tissue, metastatic calcification, ectopic calcification, red eye, arthralgia, myalgia, pruritus cutaneus, heart conduction disturbance, pulmonary diffusing impairment, angina pectoris, cardiac infarction, or heart failure induced by cardiac murmur or valvular disease.

95. A method for lowering the concentration of serum phosphorus in a blood stream, said method comprising the step of administering a therapeutically or prophylactically effective amount of a compound according to claim 1 or a pharmaceutically acceptable salt or solvate thereof to a mammal.

96. A method for inhibiting phosphate transport in vivo, said method comprising the step of administering a therapeutically or prophylactically effective amount of a compound according to claim 1 or a pharmaceutically acceptable salt or solvate thereof to a mammal.