Substituted guanidines as fungicides

Information

  • Patent Grant
  • 10111437
  • Patent Number
    10,111,437
  • Date Filed
    Friday, June 3, 2016
    8 years ago
  • Date Issued
    Tuesday, October 30, 2018
    6 years ago
Abstract
A novel guanidine compound having excellent fungicidal activity is represented by formula [I]. (In the formula, Y represents a divalent group represented by formula [II] (wherein each of R7-R9 independently represents a hydrogen atom or the like) or the like; each of X and Z independently represents an unsubstituted or substituted alkylene group or the like; each of Q1 and Q2 independently represents a single bond or the like; each of A1 and A2 independently represents an unsubstituted or substituted divalent heterocyclic compound residue or the like; and each of R1-R6 independently represents a hydrogen atom or the like.)
Description
TECHNICAL FIELD

The present invention relates to a guanidine compound and a fungicide. More particularly, the present invention relates to a novel guanidine compound which has excellent fungicidal activity, is safe to use, and can be industrially advantageously synthesized, as well as a fungicide or a plant disease-controlling agent containing the guanidine compound as an active ingredient thereof.


CROSS-REFERENCE TO RELATED APPLICATIONS

The present invention is a National Stage application of PCT/JP2016/066603, filed Jun. 3, 2016, which claims priority on the basis of Japanese Patent Application No. 2015-113376 filed in Japan on Jun. 3, 2015, the contents of which are incorporated herein by reference.


BACKGROUND OF THE INVENTION

Patent Document 1, 2, 3, and 4 disclose that some arylamidine compounds have controlling effects against fungi or disease pathogens. In addition, fungicides or plant disease-controlling agents containing the arylamidine compounds as active ingredients thereof have been proposed.


DOCUMENTS OF RELATED ART
Patent Documents



  • Patent Document 1: WO 2013/062024 A1

  • Patent Document 2: WO 2006/011499 A1

  • Patent Document 3: WO 2007/074868 A1

  • Patent Document 4: WO 2003/074476 A1



SUMMARY OF THE INVENTION
Problems to be Solved by the Invention

The present invention aims to provide a novel guanidine compound which has excellent fungicidal activity, is safe to use, and can be industrially advantageously synthesized, as well as a fungicide or a plant disease-controlling agent containing the guanidine compounds as an active ingredient thereof.


Means to Solve the Problems

The present invention encompasses the following aspects.

  • [1] A compound represented by formula [I] or a salt thereof.




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In the formula [I],


Y represents a divalent group represented by formula [II], [IIa], or [IIb].




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In the formula [II], R7 to R9 each independently represents a hydrogen atom, a nitro group, a cyano group, an unsubstituted or substituted hydrocarbon group, an unsubstituted or substituted heterocyclyl group, a hydroxyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted alkoxycarbonyl group, an unsubstituted or substituted aryloxy group, an unsubstituted or substituted amino group, an unsubstituted or substituted alkylsulfonyl group, an unsubstituted or substituted arylsulfonyl group, an unsubstituted or substituted heterocyclylsulfonyl group, an unsubstituted or substituted alkylcarbonyl group, an unsubstituted or substituted arylcarbonyl group, or an unsubstituted or substituted heterocyclylcarbonyl group. Both R8 and R9, both R7 and R8, or both R7 and R9 may be bonded together to form a divalent organic group. Both R8 and a substituent on X may be bonded together to form a divalent organic group. * represents a binding site.




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In the formula [IIa] and formula [IIb], R10 to R15 each independently represents a hydrogen atom, a nitro group, a cyano group, an unsubstituted or substituted hydrocarbon group, an unsubstituted or substituted heterocyclyl group, a hydroxyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted alkoxycarbonyl group, an unsubstituted or substituted aryloxy group, an unsubstituted or substituted amino group, an unsubstituted or substituted alkylsulfonyl group, an unsubstituted or substituted arylsulfonyl group, an unsubstituted or substituted heterocyclylsulfonyl group, an unsubstituted or substituted alkylcarbonyl group, an unsubstituted or substituted arylcarbonyl group, or an unsubstituted or substituted heterocyclylcarbonyl group. Both R10 and R11, both R10 and R12, both R13 and R14, or both R14 and R15 may be bonded together to form a divalent organic group. * represents a binding site.


X and Z each independently represents an unsubstituted or substituted alkylene group, an unsubstituted or substituted alkenylene group, an unsubstituted or substituted alkynylene group, -Ta-O-Tb-, -Ta-S-Tb-, or -Ta-N(R21)-Tb-. Ta and Tb each independently represents a single bond or an unsubstituted or substituted alkylene group, R21 represents a hydrogen atom, an unsubstituted or substituted hydrocarbon group, an unsubstituted or substituted heterocyclyl group, a hydroxyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted alkoxycarbonyl group, an unsubstituted or substituted aryloxy group, an unsubstituted or substituted amino group, an unsubstituted or substituted alkylsulfonyl group, an unsubstituted or substituted arylsulfonyl group, an unsubstituted or substituted heterocyclylsulfonyl group, an unsubstituted or substituted alkylcarbonyl group, an unsubstituted or substituted arylcarbonyl group, or an unsubstituted or substituted heterocyclylcarbonyl group.


Q1 and Q2 each independently represents a single bond, an unsubstituted or substituted phenylene group, —CH═CH—, —C≡C—, —O—, —S—, —SO—, —SO2—, or —N(R22)—. R22 represents a hydrogen atom, an unsubstituted or substituted hydrocarbon group, an unsubstituted or substituted heterocyclyl group, a hydroxyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted alkoxycarbonyl group, an unsubstituted or substituted aryloxy group, an unsubstituted or substituted amino group, an unsubstituted or substituted alkylsulfonyl group, an unsubstituted or substituted arylsulfonyl group, an unsubstituted or substituted heterocyclylsulfonyl group, an unsubstituted or substituted alkylcarbonyl group, an unsubstituted or substituted arylcarbonyl group, or an unsubstituted or substituted heterocyclylcarbonyl group.


A1 and A2 each independently represents an unsubstituted or substituted divalent heterocyclic compound residue, an unsubstituted or substituted divalent aromatic hydrocarbon residue, or —N(R23)—. R23 represents a hydrogen atom, an unsubstituted or substituted hydrocarbon group, an unsubstituted or substituted heterocyclyl group, a hydroxyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted alkoxycarbonyl group, an unsubstituted or substituted aryloxy group, an unsubstituted or substituted amino group, an unsubstituted or substituted alkylsulfonyl group, an unsubstituted or substituted arylsulfonyl group, an unsubstituted or substituted heterocyclylsulfonyl group, an unsubstituted or substituted alkylcarbonyl group, an unsubstituted or substituted arylcarbonyl group, or an unsubstituted or substituted heterocyclylcarbonyl group.


R1 to R6 each independently represents a hydrogen atom, an unsubstituted or substituted hydrocarbon group, an unsubstituted or substituted heterocyclyl group, a hydroxyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted alkoxycarbonyl group, an unsubstituted or substituted aryloxy group, an unsubstituted or substituted amino group, an unsubstituted or substituted alkylsulfonyl group, an unsubstituted or substituted arylsulfonyl group, an unsubstituted or substituted heterocyclylsulfonyl group, an unsubstituted or substituted alkylcarbonyl group, an unsubstituted or substituted arylcarbonyl group, or an unsubstituted or substituted heterocyclylcarbonyl group. R1 and R2 may be bonded together to form a 4- to 8-membered ring with two nitrogen atoms binding therewith and a carbon atom binding with the two nitrogen atoms, R2 and R3 may be bonded together to form a 4- to 8-membered ring with a nitrogen atom binding therewith, R4 and R5 may be bonded together to form a 4- to 8-membered ring with two nitrogen atoms binding therewith and a carbon atom binding with the two nitrogen atoms, or R5 and R6 may be bonded together to form a 4- to 8-membered ring with a nitrogen atom binding therewith.

  • [2] The compound or the salt thereof according to [1], wherein Y in the formula [I]represents a divalent group represented by formula [II], and the divalent group represented by formula [II] represents a divalent group represented by formula [III].




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In the formula [III], R51 represents an unsubstituted or substituted alkylene group, an unsubstituted or substituted alkenylene group, or an unsubstituted or substituted phenylene group. R50 each independently represents a hydrogen atom, a nitro group, a cyano group, an unsubstituted or substituted hydrocarbon group, an unsubstituted or substituted heterocyclyl group, a hydroxyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted alkoxycarbonyl group, an unsubstituted or substituted aryloxy group, an unsubstituted or substituted amino group, an unsubstituted or substituted alkylsulfonyl group, an unsubstituted or substituted arylsulfonyl group, an unsubstituted or substituted heterocyclylsulfonyl group, an unsubstituted or substituted alkylcarbonyl group, an unsubstituted or substituted arylcarbonyl group, or an unsubstituted or substituted heterocyclylcarbonyl group. * represents a binding site.

  • [3] A fungicide containing at least one selected from the compound and the salt thereof according to [1] as an active ingredient thereof.
  • [4] A plant disease-controlling agent containing at least one selected from the compound and the salt thereof according to [1] as an active ingredient thereof.


Effects of the Invention

The guanidine compound (the compound of formula [I] or the salt thereof) according to the present invention has excellent fungicidal activity, is safe to use, and can be industrially advantageously synthesized. The fungicide or the plant disease-controlling agent containing the guanidine compound as an active ingredient thereof is particularly excellent in controlling plant diseases such as apple scab disease, cucumber gray mold disease, wheat powdery mildew disease, tomato late blight disease, or wheat leaf rust disease.







EMBODIMENTS FOR CARRYING OUT THE INVENTION

First, in the present invention, the term “unsubstituted” refers to a group consisting of a mother nucleus. In the case where only a name of a group serving as a mother nucleus is provided without being indicated with the term “substituted”, this refers to “unsubstituted” unless specifically indicated otherwise.


On the other hand, the term “substituted” refers to any hydrogen atom of a group serving as a mother nucleus being substituted with a group having a structure that is the same as or different from the mother nucleus. Thus, a “substituent” is another group bound to a group serving as the mother nucleus. There may be one substituent or two or more substituents. Two or more substituents may be the same or different.


The term “C1-6”, for example, indicates that the number of carbon atoms of the group serving as the mother nucleus is 1 to 6. The number of carbon atoms does not include the number of carbon atoms present in substituents. For example, a butyl group having an ethoxy group as a substituent thereof is classified as a C2 alkoxy C4 alkyl group.


There are no particular limitations on “substituents” provided that they are chemically available and achieve the effects of the present invention. Examples of groups that can be “substituents” include the following groups.


C1-6 alkyl groups such as a methyl group, an ethyl group, a n-propyl group, an i-propyl group, a n-butyl group, a s-butyl group, an i-butyl group, a t-butyl group, a n-pentyl group, and a n-hexyl group;


C2-6 alkenyl groups such as a vinyl group, a 1-propenyl group, a 2-propenyl group (allyl group), a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-methyl-2-propenyl group, and a 2-methyl-2-propenyl group;


C2-6 alkynyl groups such as an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, and a 1-methyl-2-propynyl group;


C3-8 cycloalkyl groups such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group;


C4-8 cycloalkenyl groups such as a 2-cyclopentenyl group, a 3-cyclohexenyl group, and a 4-cyclooctenyl group;


C6-10 aryl groups such as a phenyl group and naphthyl group;


C7-11 aralkyl groups such as a benzyl group and a phenethyl group;


3- to 6-membered heterocyclyl groups;


C1-7 acyl groups such as a formyl group, an acetyl group, a propionyl group, a benzoyl group, and a cyclohexylcarbonyl group;


a hydroxyl group;


C1-6 alkoxy groups such as a methoxy group, an ethoxy group, a n-propoxy group, an i-propoxy group, a n-butoxy group, a s-butoxy group, an i-butoxy group, and a t-butoxy group;


C2-6 alkenyloxy groups such as a vinyloxy group, an allyloxy group, a propenyloxy group, and a butenyloxy group;


C2-6 alkynyloxy groups such as an ethynyloxy group and a propargyloxy group;


C6-10 aryloxy groups such as a phenoxy group and a naphthoxy group;


C7-11 aralkyloxy groups such as a benzyloxy group and a phenethyloxy group;


C1-7 acyloxy groups such as a formyloxy group, an acetyloxy group, a propionyloxy group, a benzoyloxy group, and a cyclohexylcarbonyloxy group;


C1-6 alkoxycarbonyl groups such as a methoxycarbonyl group, an ethoxycarbonyl group, a n-propoxycarbonyl group, an i-propoxycarbonyl group, a n-butoxycarbonyl group, and a t-butoxycarbonyl group;


C1-6 alkoxycarbonyloxy groups such as a methoxycarbonyloxy group, an ethoxycarbonyloxy group, a n-propoxycarbonyloxy group, an i-propoxycarbonyloxy group, a n-butoxycarbonyloxy group, and a t-butoxycarbonyloxy group;


a carboxyl group;

    • halogeno groups such as a fluoro group, a chloro group, a bromo group, and an iodo group;
    • C1-6 haloalkyl groups such as a chloromethyl group, a chloroethyl group, a trifluoromethyl group, a 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group, and a perfluoro-n-pentyl group;


C2-6 haloalkenyl groups such as a 2-chloro-1-propenyl group, and a 2-fluoro-1-butenyl group;


C2-6 haloalkynyl groups such as a 4,4-dichloro-1-butynyl group, a 4-fluoro-1-pentynyl group, and a 5-bromo-2-pentynyl group;


C6-10 haloaryl groups such as a 4-chlorophenyl group, a 4-fluorophenyl group, and a 2,4-dichlorophenyl group;


C1-6 haloalkoxy groups such as a trifluoromethoxy group, a 2-chloro-n-propoxy group, and a 2,3-dichlorobutoxy group;


C2-6 haloalkenyloxy groups such as a 2-chloropropenyloxy group and a 3-bromobutenyloxy group;


C6-10 haloaryloxy groups such as a 4-fluorophenyloxy group and a 4-chloro-1-naphthoxy group;


C1-7 haloacyl groups such as a chloroacetyl group, a trifluoroacetyl group, a trichloroacetyl group and a 4-chlorobenzoyl group;


an amino group (a group represented by NH2);


C1-6 alkyl substituted-amino groups such as a methylamino group, a dimethylamino group and a diethylamino group;


C6-10 arylamino groups such as an anilino group and a naphthylamino group;


C7-11 aralkylamino groups such as a benzylamino group and a phenethylamino group;


C1-7 acylamino groups such as a formylamino group, an acetylamino group, a propanoylamino group, a butyrylamino group, an i-propylcarbonylamino group, and a benzoylamino group;


C1-6 alkoxycarbonylamino groups such as a methoxycarbonylamino group, an ethoxycarbonylamino group, a n-propoxycarbonylamino group, and an i-propoxycarbonylamino group;


unsubstituted or substituted aminocarbonyl groups such as an aminocarbonyl group, a dimethylaminocarbonyl group, a phenylaminocarbonyl group, and a N-phenyl-N-methylaminocarbonyl group;


imino C1-6 alkyl groups such as an iminomethyl group, a (1-imino)ethyl group, and a (1-imino)-n-propyl group;


an unsubstituted or substituted N-hydroxyimino C1-6 alkyl groups such as a N-hydroxy-iminomethyl group, a (1-(N-hydroxy)-imino)ethyl group, a (1-(N-hydroxy)-imino)propyl group, an N-methoxy-iminomethyl group, and a (1-(N-methoxy)-imino)ethyl group;


a mercapto group;


C1-6 alkylthio groups such as a methylthio group, an ethylthio group, a n-propylthio group, an i-propylthio group, a n-butylthio group, an i-butylthio group, a s-butylthio group, and a t-butylthio group;


C6-10 arylthio groups such as a phenylthio group and a naphthylthio group;


heteroarylthio groups such as a thiazolylthio group and a pyridylthio group;


C7-11 aralkylthio groups such as a benzylthio group and a phenethylthio group;


C1-6 alkylsulfinyl groups such as a methylsulfinyl group, an ethylsulfinyl group, and a t-butylsulfinyl group;


C6-10 arylsulfinyl groups such as a phenylsulfinyl group;


heteroarylsulfinyl groups such as a thiazolylsulfinyl group and a pyridylsulfinyl group;


C7-11 aralkylsulfinyl groups such as a benzylsulfinyl group and a phenethylsulfinyl group;


C1-6 alkylsulfonyl groups such as a methylsulfonyl group, an ethylsulfonyl group, and a t-butylsulfonyl group;


C6-10 arylsulfonyl groups such as a phenylsulfonyl group;


heteroarylsulfonyl groups such as a thiazolylsulfonyl group and a pyridylsulfonyl group;


C7-11 aralkylsulfonyl group such as a benzylsulfonyl group and a phenethylsulfonyl group;


an aminocarbonyloxy group;


C1-6 alkyl-substituted aminocarbonyloxy groups such as an ethylaminocarbonyloxy group and a dimethylaminocarbonyloxy group;


tri C1-6 alkyl-substituted silyl groups such as a trimethylsilyl group, a triethylsilyl group, and a t-butyldimethylsilyl group;


triaryl-substited silyl groups such as a triphenyl silyl group;


a cyano group; a nitro group; and an oxo group.


In addition, any hydrogen atoms in these “substituents” may also be substituted with other “substituents” having a different structure.


The “3- to 6-membered heterocyclyl group” contains as constituent atoms of its ring 1 to 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and sulfur atom. The heterocyclyl group may be monocyclic or polycyclic. As long as at least one of rings of a polycyclicheterocyclyl group is a hetero ring, the remaining rings may be saturated alicyclic rings, unsaturated alicyclic rings, or aromatic rings. Examples of the “3- to 6-membered heterocyclyl group” include: 3- to 6-membered saturated heterocyclyl groups, 5- to 6-membered heteroaryl groups, and 5- to 6-membered partially unsaturated heterocyclyl groups.


Examples of the 3- to 6-membered saturated heterocyclyl groups include an aziridinyl group, an epoxy group, a pyrrolidinyl group, a tetrahydrofuranyl group, a thiazolidinyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, a dioxolanyl group, and a dioxanyl group.


Examples of 5-membered heteroaryl groups include a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group, and a tetrazolyl group.


Examples of 6-membered heteroaryl groups include a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, and a triazinyl group.


A guanidine compound according to the present invention is a compound represented by formula [I] (which, hereinafter, may be abbreviated as compound [I]) or a salt thereof.




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In the formula [I], Y represents a divalent group represented by formula [II], formula [IIa], or formula [IIb], and preferably represents a divalent group represented by formula [II].




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In the formula [II], R7 to R9 each independently represents a hydrogen atom, a nitro group, a cyano group, an unsubstituted or substituted hydrocarbon group, an unsubstituted or substituted heterocyclyl group, a hydroxyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted alkoxycarbonyl group, an unsubstituted or substituted aryloxy group, an unsubstituted or substituted amino group, an unsubstituted or substituted alkylsulfonyl group, an unsubstituted or substituted arylsulfonyl group, an unsubstituted or substituted heterocyclylsulfonyl group, an unsubstituted or substituted alkylcarbonyl group, an unsubstituted or substituted arylcarbonyl group, or an unsubstituted or substituted heterocyclylcarbonyl group.


In the formula [II], * represents a binding site.


The “hydrocarbon group” for R7 to R9 is a group formed by removing a hydrogen atom from a hydrocarbon compound. Examples of the hydrocarbon compound include: saturated hydrocarbon compounds such as a methane, an ethane, a propane, a butane, a pentane, a hexane, and a heptane; unsaturated hydrocarbon compounds such as an ethylene, an acetylene, and a propylene; alicyclic hydrocarbon compounds such as a cyclopentane, a cyclohexane, and a cyclohexene; and aromatic hydrocarbon compounds such as a benzene and a naphthalene. Among these, the “hydrocarbon group” is preferably a C1-6 alkyl group or a C6-10 aryl group, and more preferably a C1-6 alkyl group or a phenyl group.


The “heterocyclyl group” for R7 to R9 is a group formed by formed by removing a hydrogen atom from a heterocyclic compound. Examples of the heterocyclyl group include an aziridinyl group, an epoxy group, a pyrrolidinyl group, a tetrahydrofuranyl group, a thiazolidinyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, a dioxolanyl group, a dioxanyl group; a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group, a tetrazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, and a triazinyl group.


Examples of the “alkoxy group” for R7 to R9 include a methoxy group, an ethoxy group, a n-propoxy group, an i-propoxy group, a n-butoxy group, a s-butoxy group, an i-butoxy group, and a t-butoxy group, and a C1-6 alkoxy group is preferable.


Examples of the “alkoxycarbonyl group” for R7 to R9 include a methoxycarbonyl group, an ethoxycarbonyl group, a n-propoxycarbonyl group, an i-propoxycarbonyl group, a n-butoxycarbonyl group, a s-butoxycarbonyl group, an i-butoxycarbonyl group, and a t-butoxycarbonyl group, and a C1-6 alkoxycarbonyl group is preferable.


Examples of the “aryloxy group” for R7 to R9 include a phenoxy group and a naphthoxy group, and a phenoxy group is preferable.


Examples of the “unsubstituted or substituted amino group” for R7 to R9 include an amino group (represented by NH2); C1-6 alkyl-substituted amino groups such as a methylamino group, a dimethylamino group, and a diethylamino group; C6-10 arylamino groups such as an anilino group and a naphthylamino group; C7-11 aralkylamino groups such as a benzylamino group and a phenethylamino group; C1-7 acylamino groups such as a formylamino group, an acetylamino group, a propanoylamino group, a butyrylamino group, an i-propylcarbonylamino group, and a benzoylamino group; C1-6 alkoxycarbonylamino groups such as a methoxycarbonylamino group, an ethoxycarbonylamino group, a n-propoxycarbonylamino group, and an i-propoxycarbonylamino group.


Examples of the “alkylsulfonyl group” for R7 to R9 include a methylsulfonyl group, an ethylsulfonyl group, a n-propylsulfonyl group, an i-propylsulfonyl group, a n-butylsulfonyl group, a s-butylsulfonyl group, an i-butylsulfonyl group, and a t-butylsulfonyl group, and a C1-6 alkylsulfonyl group is preferable.


Examples of the “arylsulfonyl group” for R7 to R9 include a phenylsulfonyl group and a naphthylsulfonyl group, and a phenylsulfonyl group is preferable.


Examples of the “heterocyclylsulfonyl group” for R7 to R9 include an aziridinylsulfonyl group, an epoxysulfonyl group, a pyrrolidinylsulfonyl group, a tetrahydrofuranylsulfonyl group, a thiazolidinylsulfonyl group, a piperidylsulfonyl group, a piperazinylsulfonyl group, a morpholinylsulfonyl group, a dioxolanylsulfonyl group, a dioxanylsulfonyl group; a pyrrolylsulfonyl group, a furylsulfonyl group, a thienylsulfonyl group, an imidazolylsulfonyl group, a pyrazolylsulfonyl group, an oxazolylsulfonyl group, an isoxazolylsulfonyl group, a thiazolylsulfonyl group, an isothiazolylsulfonyl group, a triazolylsulfonyl group, an oxadiazolylsulfonyl group, a thiadiazolylsulfonyl group, a tetrazolylsulfonyl group, a pyridylsulfonyl group, a pyrazinylsulfonyl group, a pyrimidinylsulfonyl group, a pyridazinylsulfonyl group, and a triazinylsulfonyl group.


Examples of the “alkylcarbonyl group” for R7 to R9 include a methylcarbonyl group, an ethylcarbonyl group, a n-propylcarbonyl group, an i-propylcarbonyl group, a n-butylcarbonyl group, a s-butylcarbonyl group, an i-butylcarbonyl group, and a t-butylcarbonyl group, and a C1-6 alkylcarbonyl group is preferable. As a substituent thereof, a halogeno group is preferable among the above-mentioned substituents.


Examples of the “arylcarbonyl group” for R7 to R9 include a phenylcarbonyl group and a naphthylcarbonyl group, and a phenylcarbonyl group is preferable.


Examples of the “heterocyclylcarbonyl group” for R7 to R9 include an aziridinylcarbonyl group, an epoxycarbonyl group, a pyrrolidinylcarbonyl group, a tetrahydrofuranylcarbonyl group, a thiazolidinylcarbonyl group, a piperidylcarbonyl group, a piperazinylcarbonyl group, a morpholinylcarbonyl group, a dioxolanylcarbonyl group, a dioxanylcarbonyl group; a pyrrolylcarbonyl group, a furylcarbonyl group, a thienylcarbonyl group, an imidazolylcarbonyl group, a pyrazolylcarbonyl group, an oxazolylcarbonyl group, an isoxazolylcarbonyl group, a thiazolylcarbonyl group, an isothiazolylcarbonyl group, a triazolylcarbonyl group, an oxadiazolylcarbonyl group, a thiadiazolylcarbonyl group, a tetrazolylcarbonyl group, a pyridylcarbonyl group, a pyrazinylcarbonyl group, a pyrimidinylcarbonyl group, a pyridazinylcarbonyl group, and a triazinylcarbonyl group.


Among these, it is preferable that R7 to R9 in formula [II] each independently represents a hydrogen atom, a nitro group, a cyano group, an unsubstituted or substituted hydrocarbon group, an unsubstituted or substituted alkoxycarbonyl group, or an unsubstituted or substituted alkylcarbonyl group.


In formula [II], R8 and R9, R7 and R8, or R7 and R9 may be bonded together to form a divalent organic group. In the case where R8 and R9 are bonded together to form a divalent organic group, examples thereof include a divalent organic group represented by formula [III].




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In the formula [III], R51 represents an unsubstituted or substituted alkylene group, an unsubstituted or substituted alkenylene group, or an unsubstituted or substituted phenylene group.


Examples of the “alkylene group” for R51 include a methylene group, an ethylene group, a propane-1,3-diyl group (another name: trimethylene group), a propane-1,2-diyl group (another name: propylene group), a butane-1,4-diyl group, a butane-1,3-diyl group, a butane-1,2-diyl group, a pentane-1,5-diyl group, a hexane-1,6-diyl group, a heptane-1,7-diyl group, and an octane-1,8-diyl group, and an ethylene group is preferable.


Examples of the “alkenylene group” for R51 include an ethene-1,2-diyl group (—CH═CH—) group, a propenylene group and 2-butenylene group, and an ethene-1,2-diyl group is preferable.


Examples of the “phenylene group” for R51 include a 1,2-phenylene group.


Preferable examples of a substituent on the “alkylene group” or “alkenylene group” for R51 include a C1-6 alkyl group, a C6-10 aryl group, a hydroxyl group, a C1-6 alkoxy group, a C6-10 aryloxy group, a carboxyl group, a halogeno group, a C1-6 haloalkyl group, a C6-10 haloaryl group, a C1-6 haloalkoxy group, an amino group (represented by NH2), a C1-6 alkyl-substituted amino group, a C6-10 arylamino group, a C1-7 acylamino group, a C1-6 alkylthiogroup, a C6-10 arylthio group, a heteroarylthio group, a C1-6 alkylsulfinyl group, a C1-6 alkylsulfonyl group, a C6-10 arylsulfonyl group, a heteroarylsulfonyl group, a cyano group, and an oxo group, and a C1-6 alkyl group or a C6-10 aryl group (phenyl group) is more preferable.


Examples of substituents on the “phenylene group” for R51 include C1-6 alkyl groups, C3 to 8 cycloalkyl groups, C6-10 aryl groups, 3- to 6-membered heterocyclyl groups, a hydroxyl group, C1-6 alkoxy groups, C6-10 aryloxy groups, a carboxyl group, halogeno groups, C1-6 haloalkyl groups, C6-10 haloaryl groups, C1-6 haloalkoxy groups, an amino group (represented by NH2), C1-6 alkyl-substituted amino group, C6-10 arylamino groups, C1-7 acylamino groups, C1-6 alkoxycarbonylamino groups, C1-6 alkyl thio groups, C6-10 arylthio groups, heteroarylthio groups, C7-11 aralkylthio groups, C1-6 alkylsulfinyl groups, C6-10 arylsulfinyl groups, heteroarylsulfinyl groups, C7-11 aralkyl sulfinyl groups, C1-6 alkylsulfonyl groups, C6-10 arylsulfonyl groups, heteroarylsulfonyl groups, a cyano group, and a nitro group.


In the formula [III], R50 each independently represents a hydrogen atom, a nitro group, a cyano group, an unsubstituted or substituted hydrocarbon group, an unsubstituted or substituted heterocyclyl group, a hydroxyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted alkoxycarbonyl group, an unsubstituted or substituted aryloxy group, an unsubstituted or substituted amino group, an unsubstituted or substituted alkylsulfonyl group, an unsubstituted or substituted arylsulfonyl group, an unsubstituted or substituted heterocyclylsulfonyl group, an unsubstituted or substituted alkylcarbonyl group, an unsubstituted or substituted arylcarbonyl group, or an unsubstituted or substituted heterocyclylcarbonyl group.


Examples of the “hydrocarbon group”, “heterocyclyl group”, “alkoxy group”, “alkoxycarbonyl group”, “aryloxy group”, “unsubstituted or substituted amino group”, “alkylsulfonyl group”, “arylsulfonyl group”, “heterocyclylsulfonyl group”, “alkylcarbonyl group”, “arylcarbonyl group”, or “heterocyclylcarbonyl group” for R50 in formula [III] include the same groups as those exemplified for R7 to R9 in the formula [II]. Among these, R50 preferably represents a hydrogen atom, a nitro group, or an unsubstituted or substituted alkylcarbonyl group, and more preferably represents a hydrogen atom, a nitro group, a C1-6 alkylcarbonyl group, or a C1-6 haloalkylcarbonyl group.


In the formula [III], * represents a binding site.


R8 and a substituent on X may be bonded together to form a divalent organic group (such as a C1-3 alkylene group).




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In the formula [IIa] and formula [IIb], R10 to R15 each independently represents a hydrogen atom, a nitro group, a cyano group, an unsubstituted or substituted hydrocarbon group, an unsubstituted or substituted heterocyclyl group, a hydroxyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted alkoxycarbonyl group, an unsubstituted or substituted aryloxy group, an unsubstituted or substituted amino group, an unsubstituted or substituted alkylsulfonyl group, an unsubstituted or substituted arylsulfonyl group, an unsubstituted or substituted heterocyclylsulfonyl group, an unsubstituted or substituted alkylcarbonyl group, an unsubstituted or substituted arylcarbonyl group, or an unsubstituted or substituted heterocyclylcarbonyl group.


In the formula [IIa] and formula [IIb], * represents a binding site.


The “hydrocarbon group” for R10 to R15 is a group formed by removing a hydrogen atom from a hydrocarbon compound. Examples of the hydrocarbon compound include: saturated hydrocarbon compounds such as methane, ethane, propane, butane, pentane, hexane, and heptane; unsaturated hydrocarbon compounds such as ethylene, acetylene, and propylene; alicyclic hydrocarbon compounds such as cyclopentane, cyclohexane, and cyclohexene; and aromatic hydrocarbon compounds such as benzene and naphthalene.


The “heterocyclyl group” for R10 to R15 is a group formed by removing a hydrogen atom from a heterocyclic compound. Examples of the heterocyclyl group include an aziridinyl group, an epoxy group, a pyrrolidinyl group, a tetrahydrofuranyl group, a thiazolidinyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, a dioxolanyl group, a dioxanyl group; a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group, a tetrazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, and a triazinyl group.


Examples of the “alkoxy group” for R10 to R15 include a methoxy group, an ethoxy group, a n-propoxy group, an i-propoxy group, a n-butoxy group, a s-butoxy group, an i-butoxy group, and a t-butoxy group.


Examples of the “alkoxycarbonyl group” for R10 to R15 include a methoxycarbonyl group, an ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, a s-butoxycarbonyl group, an i-butoxycarbonyl group, and a t-butoxycarbonyl group.


Examples of the “aryloxy group” for R10 to R15 include a phenoxy group and a naphthoxy group.


Examples of the “unsubstituted or substituted amino group” for R10 to R15 include: an amino group (represented by NH2); C1-6 alkyl-substituted amino groups such as a methylamino group, a dimethylamino group, and a diethylamino group; C6-10 arylamino groups such as an anilino group and a naphthylamino group; C7-11 aralkyl amino groups such as a benzylamino group and a phenethylamino group; C1-7 acylamino groups such as a formylamino group, an acetylamino group, a propanoylamino group, a butyrylamino group, an i-propylcarbonylamino group, and a benzoylamino group; C1-6 alkoxycarbonylamino groups such as a methoxycarbonylamino group, an ethoxycarbonylamino group, a n-propoxycarbonylamino group, and an i-propoxycarbonylamino group.


Examples of the “alkylsulfonyl group” for R10 to R15 include a methylsulfonyl group, an ethylsulfonyl group, a n-propylsulfonyl group, an i-propylsulfonyl group, a n-butylsulfonyl group, a s-butylsulfonyl group, an i-butylsulfonyl group, and a t-butylsulfonyl group.


Examples of the “arylsulfonyl group” for R10 to R15 include a phenylsulfonyl group and a naphthylsulfonyl group.


Examples of the “heterocyclylsulfonyl group” for R10 to R15 include an aziridinylsulfonyl group, an epoxysulfonyl group, a pyrrolidinylsulfonyl group, a tetrahydrofuranylsulfonyl group, a thiazolidinylsulfonyl group, a piperidylsulfonyl group, a piperazinylsulfonyl group, a morpholinylsulfonyl group, a dioxolanylsulfonyl group, a dioxanylsulfonyl group; a pyrrolylsulfonyl group, a furylsulfonyl group, a thienylsulfonyl group, an imidazolylsulfonyl group, a pyrazolylsulfonyl group, an oxazolylsulfonyl group, an isoxazolylsulfonyl group, a thiazolylsulfonyl group, an isothiazolylsulfonyl group, a triazolylsulfonyl group, an oxadiazolylsulfonyl group, a thiadiazolylsulfonyl group, a tetrazolylsulfonyl group, a pyridylsulfonyl group, a pyrazinylsulfonyl group, a pyrimidinylsulfonyl group, a pyridazinyl sulfonyl group, and a triazinylsulfonyl group.


Examples of the “alkylcarbonyl group” for R10 to R15 include a methylcarbonyl group, an ethylcarbonyl group, a n-propylcarbonyl group, an i-propylcarbonyl group, a n-butylcarbonyl group, a s-butylcarbonyl group, an i-butylcarbonyl group, and a t-butylcarbonyl group.


Examples of the “arylcarbonyl group” for R10 to R15 include a phenylcarbonyl group and a naphthylcarbonyl group.


Examples of the “heterocyclylcarbonyl group” for R10 to R15 include an aziridinylcarbonyl group, an epoxycarbonyl group, a pyrrolidinylcarbonyl group, a tetrahydrofuranylcarbonyl group, a thiazolidinylcarbonyl group, a piperidylcarbonyl group, a piperazinylcarbonyl group, a morpholinylcarbonyl group, a dioxolanylcarbonyl group, a dioxanylcarbonyl group; a pyrrolylcarbonyl group, a furylcarbonyl group, a thienylcarbonyl group, an imidazolylcarbonyl group, a pyrazolylcarbonyl group, an oxazolylcarbonyl group, an isoxazolylcarbonyl group, a thiazolylcarbonyl group, an isothiazolylcarbonyl group, a triazolylcarbonyl group, an oxadiazolylcarbonyl group, a thiadiazolylcarbonyl group, a tetrazolylcarbonyl group, a pyridylcarbonyl group, a pyrazinylcarbonyl group, a pyrimidinylcarbonyl group, a pyridazinylcarbonyl group, and a triazinylcarbonyl group.


In the formula [IIa] and formula [IIb], both R10 and R11, both R10 and R12, both R13 and R14, or both R14 and R15 may be bonded together to form a divalent organic group.


Among these, it is preferable that R10 to R15 each independently represents a hydrogen atom, a C1-6 alkyl group, or a phenyl group.


In the formula [I], X and Z each independently represents an unsubstituted or substituted alkylene group, an unsubstituted or substituted alkenylene group, an unsubstituted or substituted alkynylene group, -Ta-O-Tb-, -Ta-S-Tb-, or -Ta-N(R21)-Tb-. Ta and Tb each independently represents a single bond or an unsubstituted or substituted alkylene group, and R21 represents a hydrogen atom, an unsubstituted or substituted hydrocarbon group, an unsubstituted or substituted heterocyclyl group, a hydroxyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted alkoxycarbonyl group, an unsubstituted or substituted aryloxy group, an unsubstituted or substituted amino group, an unsubstituted or substituted alkylsulfonyl group, an unsubstituted or substituted arylsulfonyl group, an unsubstituted or substituted heterocyclylsulfonyl group, an unsubstituted or substituted alkylcarbonyl group, an unsubstituted or substituted arylcarbonyl group or an unsubstituted or substituted heterocyclylcarbonyl group.


Examples of the “hydrocarbon group”, “heterocyclyl group”, “alkoxy group”, “alkoxycarbonyl group”, “aryloxy group”, “unsubstituted or substituted amino group”, “alkylsulfonyl group”, “arylsulfonyl group”, “heterocyclylsulfonyl group”, “alkylcarbonyl group”, “arylcarbonyl group”, or “heterocyclylcarbonyl group” for R21 include the same groups as those exemplified for R7 to R9 in the formula [II].


Examples of the “alkylene group” for X and Z include the same groups as those exemplified for R51 in the formula [III] and a C1-10 alkylene group is preferable.


Examples of the “alkenylene group” for X and Z include the same groups as those exemplified for R51 in the formula [III].


Examples of the “alkynylene group” for X and Z include an ethynylene group and a 2-butynylene group.


Examples fo a substituent on the “alkylene group”, “alkenylene group”, or “alkynylene group” for X or Z include C1-6 alkyl groups, C6-10 aryl groups, a hydroxyl group, C1-6 alkoxy groups, C6-10 aryloxy groups, a carboxyl group, halogeno groups, C1-6 haloalkyl groups, C6-10 haloaryl groups, C1-6 haloalkoxy groups, an amino group (represented by NH2), C1-6 alkyl-substituted amino groups, C6-10 arylamino groups, C1-7 acylamino groups, C1-6 alkylthio groups, C6-10 arylthio groups, heteroarylthio groups, C1-6 alkylsulfinyl groups, C1-6 alkylsulfonyl groups, C6-10 arylsulfonyl groups, heteroarylsulfonyl groups, a cyano group, and an oxo group.


Among these, it is preferable that X and Y each independently represents an unsubstituted or substituted alkylene group or -Ta-O-Tb- (wherein Ta and Tb each independently represents a single bond or an unsubstituted or substituted C1-6 alkylene group).


In the formula [I], Q1 and Q2 each independently represents a single bond, an unsubstituted or substituted phenylene group, an ethene-1,2-diyl group (—CH═CH—), an ethyne-1,2-diyl group (—C≡C—), an oxy group (—O—), a thio group (—S—), a sulfinyl group (—SO—), a sulfonyl group (—SO2—), or an unsubstituted or N-substituted imino group (—N(R22)—).


Examples of a substituent on the “phenylene group” for Q1 or Q2 include the same groups as those exemplified for the substituent on the phenylene group for R51 in the formula [III].


R22 represents a hydrogen atom, an unsubstituted or substituted hydrocarbon group, an unsubstituted or substituted heterocyclyl group, a hydroxyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted alkoxycarbonyl group, an unsubstituted or substituted aryloxy group, an unsubstituted or substituted amino group, an unsubstituted or substituted alkylsulfonyl group, an unsubstituted or substituted arylsulfonyl group, an unsubstituted or substituted heterocyclylsulfonyl group, an unsubstituted or substituted alkylcarbonyl group, an unsubstituted or substituted arylcarbonyl group, or an unsubstituted or substituted heterocyclylcarbonyl group.


Examples of the “hydrocarbon group”, “heterocyclyl group”, “alkoxy group”, “alkoxycarbonyl group”, “aryloxy group”, “unsubstituted or substituted amino group”, “alkylsulfonyl group”, “arylsulfonyl group”, “heterocyclylsulfonyl group”, “alkylcarbonyl group”, “arylcarbonyl group”, “heterocyclylcarbonyl group” for R22 include the same groups as those exemplified for R7 to R9 in the formula [II].


Among these, it is preferable that Q1 and Q2 each independently represents a single bond, an ethene-1,2-diyl group (—CH═CH—), an ethyne-1,2-diyl group (—C≡C—), an oxy group (—O—), or a thio group (—S—).


In the formula [I], A1 and A2 each independently represents an unsubstituted or substituted divalent heterocyclic compound residue, an unsubstituted or substituted divalent aromatic hydrocarbon residue, or —N(R23)—. R23 represents a hydrogen atom, an unsubstituted or substituted hydrocarbon group, an unsubstituted or substituted heterocyclyl group, a hydroxyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted alkoxycarbonyl group, an unsubstituted or substituted aryloxy group, an unsubstituted or substituted amino group, an unsubstituted or substituted alkylsulfonyl group, an unsubstituted or substituted arylsulfonyl group, an unsubstituted or substituted heterocyclylsulfonyl group, an unsubstituted or substituted alkylcarbonyl group, an unsubstituted or substituted arylcarbonyl group, or an unsubstituted or substituted heterocyclylcarbonyl group.


The “divalent heterocyclic compound residue” for A1 or A2 is a group formed by removing two hydrogen atoms from a heterocyclic compound. The heterocyclic compound may be either a monocyclic heterocyclic compound or a polycyclic heterocyclic compound. Examples of the monocyclic heterocyclic compound include five-membered heterocyclic compounds and six-membered heterocyclic compounds. In the case where at least one ring of the polycyclic heterocyclic compound is heterocycle, the remaining rings may be any of saturated alicycle, unsaturated alicycle and aromatic rings.


The “heterocyclic compound” is a cyclic compound containing at least 1 to 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as constituent atoms thereof.


Examples of the “monocyclic heterocyclic compound” include: 5-membered aromatic heterocyclic compounds such as imidazole, pyrazole, oxazole, thiazole, triazole, tetrazole, pyrrole, furan, and thiophene (preferably thiazole or thiophene); 6-membered aromatic heterocyclic compounds such as pyridine, pyrazine, pyrimidine, pyridazine, and triazine (preferably pyridine or pyridazine); 5-membered saturated heterocyclic compounds such as pyrrolidine, tetrahydrofuran, tetrahydrothiophene, and thiazoline; 6-membered saturated heterocyclic compounds such as piperidine, tetrahydropyran, and tetrahydrothiopyran; and 5-membered partially unsaturated heterocyclic compounds such as pyrroline, imidazoline, pyrazoline, oxazoline, and isoxazoline.


Examples of the “polycyclic heterocyclic compound” include benzofuran, benzothiophene, indole, isoindole, benzimidazole, purine, quinoline, isoquinoline, quinoxaline, cinnoline, pteridine, chromene, and isochromene, and benzofuran is preferable.


Among these, 5-membered aromatic heterocyclic compounds, 6-membered aromatic heterocyclic compounds, or polycyclic heterocyclic compounds are preferable, 6-membered aromatic heterocyclic compounds or polycyclic heterocyclic compounds are more preferable, and pyridine or benzofuran is even more preferable.


The “divalent aromatic hydrocarbon residue” for A1 or A2 is a group formed by removing two hydrogen atoms from an aromatic hydrocarbon. The aromatic hydrocarbon may be a monocycle or a polycycle. In the case where at least one ring of the polycyclic aromatic hydrocarbon is an aromatic ring, the remaining rings thereof may be any of saturated alicycles, unsaturated alicycles and aromatic rings.


Examples of the “aromatic hydrocarbon” include benzene, naphthalene, azulene, indene, indane, and tetralin. Among these, benzene or naphthalene is preferable, and benzene is more preferable.


Preferable examples of a substituent on the “divalent heterocyclic compound residue” or the “divalent aromatic hydrocarbon residue” include C1-6 alkyl groups, C3-8 cycloalkyl groups, C6-10 aryl groups, 3- to 6-membered heterocyclyl groups, a hydroxyl group, C1-6 alkoxy groups, C6-10 aryloxy groups, a carboxyl group, halogeno groups, C1-6 haloalkyl groups, C6-10 haloaryl groups, C1-6 haloalkoxy groups, an amino group (represented by NH2), C1-6 alkyl-substituted amino groups, C6-10 arylamino groups, C1-7 acylamino groups, C1-6 alkoxycarbonylamino groups, C1-6 alkylthio groups, C6-10 arylthio groups, heteroarylthio groups, C7-11 aralkylthio groups, C1-6 alkylsulfinyl groups, C6-10 arylsulfinyl groups, heteroarylsulfinyl groups, C7-11 aralkylsulfinyl groups, C1-6 alkylsulfonyl groups, C6-10 arylsulfonyl groups, heteroarylsulfonyl groups, a cyano group, and a nitro group, and a C1-6 alkyl group or a halogeno groups is more preferable.


Examples of the “hydrocarbon group”, “heterocyclyl group”, “alkoxy group”, “alkoxycarbonyl group”, “aryloxy group”, “unsubstituted or substituted amino group”, “alkylsulfonyl group”, “arylsulfonyl group”, “heterocyclylsulfonyl group”, “alkylcarbonyl group”, “arylcarbonyl group”, or “heterocyclylcarbonyl group” for R23 include the same groups as those exemplified for R7 to R9 in the formula [II]. Among these, R23 preferably represents a hydrogen atom.


R1 to R6 each independently represents a hydrogen atom, an unsubstituted or substituted hydrocarbon group, an unsubstituted or substituted heterocyclyl group, a hydroxyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted alkoxycarbonyl group, an unsubstituted or substituted aryloxy group, an unsubstituted or substituted amino group, an unsubstituted or substituted alkylsulfonyl group, an unsubstituted or substituted arylsulfonyl group, an unsubstituted or substituted heterocyclylsulfonyl group, an unsubstituted or substituted alkylcarbonyl group, an unsubstituted or substituted arylcarbonyl group, or an unsubstituted or substituted heterocyclylcarbonyl group. R1 and R2 may be bonded together to form a 4- to 8-membered ring with two nitrogen atoms binding therewith and a carbon atom binding with the two nitrogen atoms, R2 and R3 may be bonded together to form a 4- to 8-membered ring with a nitrogen atom binding therewith, R4 and R5 may be bonded together to form a 4- to 8-membered ring with two nitrogen atoms binding therewith and a carbon atom binding with the two nitrogen atoms, or R5 and R6 may be bonded together to form a 4- to 8-membered ring with a nitrogen atom binding therewith.


In the case where R1 and R2 are bonded together to form a 4- to 8-membered ring with two nitrogen atoms binding therewith and a carbon atom binding with the two nitrogen atoms, the 4- to 8-membered ring may be specifically represented by formula [IV-1], formula [IV-2], or formula [IV-3].




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In the formula [IV-1], formula [IV-2], and formula [IV-3], R3 is mentioned above.


In the formula [IV-1], formula [IV-2], and formula [IV-3], R71 each independently represents an unsubstituted or substituted hydrocarbon group, an unsubstituted or substituted heterocyclyl group, a hydroxyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted alkoxycarbonyl group, an unsubstituted or substituted aryloxy group, an unsubstituted or substituted amino group, an unsubstituted or substituted alkylsulfonyl group, an unsubstituted or substituted arylsulfonyl group, an unsubstituted or substituted heterocyclylsulfonyl group, an unsubstituted or substituted alkylcarbonyl group, an unsubstituted or substituted arylcarbonyl group, or an unsubstituted or substituted heterocyclylcarbonyl group.


Examples of the “hydrocarbon group”, “heterocyclyl group”, “alkoxy group”, “alkoxycarbonyl group”, “aryloxy group”, “unsubstituted or substituted amino group”, “alkylsulfonyl group”, “arylsulfonyl group”, “heterocyclylsulfonyl group”, “alkylcarbonyl group”, “arylcarbonyl group”, or “heterocyclylcarbonyl group” for R71 include the same groups as those exemplified for R7 to R9 in the formula [II]. Among these, it is preferable that R71 each independently represents an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C1-6 alkoxycarbonyl group, or an unsubstituted or substituted amino group (preferably unsubstituted amino group).


In the formula [IV-1], formula [IV-2], and formula [IV-3], n indicates the number of the substitutent R71 and represents an integer of 0 to 4, and preferably represents an integer of 0 to 2.


In the formula [IV-1], formula [IV-2], and formula [IV-3], * represents a binding portion with A1.


In the case where R4 and R5 are bonded together to form a 4- to 8-membered ring with two nitrogen atoms binding therewith and a carbon atom binding with the two nitrogen atoms, the 4- to 8-membered ring may be specifically represented by formula [V-1], formula [V-2], or formula [V-3].




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In the formula [V-1], formula [V-2], and formula [V-3], R6 is described above.


In the formula [V-1], formula [V-2], and formula [V-3], R81 each independently represents an unsubstituted or substituted hydrocarbon group, an unsubstituted or substituted heterocyclyl group, a hydroxyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted alkoxycarbonyl group, an unsubstituted or substituted aryloxy group, an unsubstituted or substituted amino group, an unsubstituted or substituted alkylsulfonyl group, an unsubstituted or substituted arylsulfonyl group, an unsubstituted or substituted heterocyclylsulfonyl group, an unsubstituted or substituted alkylcarbonyl group, an unsubstituted or substituted arylcarbonyl group, or an unsubstituted or substituted heterocyclylcarbonyl group.


Examples of the “hydrocarbon group”, “heterocyclyl group”, “alkoxy group”, “alkoxycarbonyl group”, “aryloxy group”, “unsubstituted or substituted amino group”, “alkylsulfonyl group”, “arylsulfonyl group”, “heterocyclylsulfonyl group”, “alkylcarbonyl group”, “arylcarbonyl group”, or “heterocyclylcarbonyl group” for R81 include the same groups as those for the substituent R71.


In the formula [V-1], formula [V-2], and formula [V-3], m represents the number of the substituent R81 and is an integer of 0 to 4 and preferably an integer of 0 to 2.


In the formula [V-1], formula [V-2], and formula [V-3], * represents a binding portion with A2.


Examples of the “hydrocarbon group”, “heterocyclyl group”, “alkoxy group”, “alkoxycarbonyl group”, “aryloxy group”, “unsubstituted or substituted amino group”, “alkylsulfonyl group”, “arylsulfonyl group”, “heterocyclylsulfonyl group”, “alkylcarbonyl group”, “arylcarbonyl group”, or “heterocyclylcarbonyl group” for R1 to R6 include the same groups as those exemplified for R7 to R9 in the formula [II].


Among these, it is preferable that R1 to R6 each independently represents a hydrogen atom, an unsubstituted or substituted hydrocarbon group (C1-6 alkyl group which is unsubstituted or substituted with a C1-6 alkyl-substituted amino group), an unsubstituted or substituted C1-6 alkoxycarbonyl group, or an unsubstituted or substituted C1-6 alkylcarbonyl group, or that both R1 and R2 or both R4 and R5 be bonded together to form a 4- to 8-membered ring with two nitrogen atoms binding therewith and a carbon atom binding with the two nitrogen atoms.


In the case where A1 and/or A2 represent —N(R23)—, R23 and R2, or R23 and R5 may be bonded together to form a 4- to 6-membered ring (preferably 5-membered ring) with two nitrogen atoms binding therewith and a carbon atom binding with the two nitrogen atoms.


Specific examples of the compound represented by the formula [I] include the following compounds.




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TABLE 1





Compound










No.
G1
G2
n
m
Ra
Rc
Q1
Q2







A-1
CH
CH
3
3
Me
H
—O—
—O—


A-2
CH
CH
3
3
Me
H
—O—
—S—


A-3
CH
CH
3
3
Me
H
—O—
—OCH2


A-4
CH
CH
3
3
Me
H
—O—
singlebond


A-5
CH
CH
3
3
Me
H
—S—
—O—


A-6
CH
CH
3
3
Me
H
—CH2O—
—O—


A-7
CH
CH
3
3
Me
H
singlebond
—O—


A-8
CH
CH
3
3
Me
H
—S—
—S—


A-9
CH
CH
3
3
Me
H
—CH2O—
—OCH2


A-10
CH
CH
3
3
Me
H
singlebond
singlebond


A-11
CH
CH
3
3
H
Me
—O—
—O—


A-12
CH
CH
3
3
H
Me
—O—
—S—


A-13
CH
CH
3
3
H
Me
—O—
—OCH2


A-14
CH
CH
3
3
H
Me
—O—
singlebond


A-15
CH
CH
3
3
H
Me
—S—
—O—


A-16
CH
CH
3
3
H
Me
—CH2O—
—O—


A-17
CH
CH
3
3
H
Me
singlebond
—O—


A-18
CH
CH
3
3
H
Me
—S—
—S—


A-19
CH
CH
3
3
H
Me
—CH2O—
—OCH2


A-20
CH
CH
3
3
H
Me
singlebond
singlebond


A-21
CH
CH
3
3
Ph
H
—O—
—O—


A-22
CH
CH
3
3
Ph
H
—O—
—S—


A-23
CH
CH
3
3
Ph
H
—O—
—OCH2


A-24
CH
CH
3
3
Ph
H
—O—
singlebond


A-25
CH
CH
3
3
Ph
H
—S—
—O—


A-26
CH
CH
3
3
Ph
H
—CH2O—
—O—


A-27
CH
CH
3
3
Ph
H
singlebond
—O—


A-28
CH
CH
3
3
Ph
H
—S—
—S—


A-29
CH
CH
3
3
Ph
H
—CH2O—
—OCH2


A-30
CH
CH
3
3
Ph
H
singlebond
singlebond


A-31
CH
CH
3
3
H
Ph
—O—
—O—


A-32
CH
CH
3
3
H
Ph
—O—
—S—


A-33
CH
CH
3
3
H
Ph
—O—
—OCH2


A-34
CH
CH
3
3
H
Ph
—O—
singlebond


A-35
CH
CH
3
3
H
Ph
—S—
—O—


A-36
CH
CH
3
3
H
Ph
—CH2O—
—O—


A-37
CH
CH
3
3
H
Ph
singlebond
—O—


A-38
CH
CH
3
3
H
Ph
—S—
—S—


A-39
CH
CH
3
3
H
Ph
—CH2O—
—OCH2


A-40
CH
CH
3
3
H
Ph
singlebond
singlebond


A-41
CH
CH
3
4
Me
H
—O—
—O—


A-42
CH
CH
3
4
Me
H
—O—
—S—


A-43
CH
CH
3
4
Me
H
—O—
—OCH2


A-44
CH
CH
3
4
Me
H
—O—
singlebond


A-45
CH
CH
3
4
Me
H
—S—
—O—


A-46
CH
CH
3
4
Me
H
—CH2O—
—O—


A-47
CH
CH
3
4
Me
H
singlebond
—O—


A-48
CH
CH
3
4
Me
H
—S—
—S—


A-49
CH
CH
3
4
Me
H
—CH2O—
—OCH2


A-50
CH
CH
3
4
Me
H
singlebond
singlebond


A-51
CH
CH
3
4
H
Me
—O—
—O—


A-52
CH
CH
3
4
H
Me
—O—
—S—


A-53
CH
CH
3
4
H
Me
—O—
—OCH2


A-54
CH
CH
3
4
H
Me
—O—
singlebond


A-55
CH
CH
3
4
H
Me
—S—
—O—


A-56
CH
CH
3
4
H
Me
—CH2O—
—O—


A-57
CH
CH
3
4
H
Me
singlebond
—O—


A-58
CH
CH
3
4
H
Me
—S—
—S—


A-59
CH
CH
3
4
H
Me
—CH2O—
—OCH2


A-60
CH
CH
3
4
H
Me
singlebond
singlebond


A-61
CH
CH
3
4
Ph
H
—O—
—O—


A-62
CH
CH
3
4
Ph
H
—O—
—S—


A-63
CH
CH
3
4
Ph
H
—O—
—OCH2


A-64
CH
CH
3
4
Ph
H
—O—
singlebond


A-65
CH
CH
3
4
Ph
H
—S—
—O—


A-66
CH
CH
3
4
Ph
H
—CH2O—
—O—


A-67
CH
CH
3
4
Ph
H
singlebond
—O—


A-68
CH
CH
3
4
Ph
H
—S—
—S—


A-69
CH
CH
3
4
Ph
H
—CH2O—
—OCH2


A-70
CH
CH
3
4
Ph
H
singlebond
singlebond


A-71
CH
CH
3
4
H
Ph
—O—
—O—


A-72
CH
CH
3
4
H
Ph
—O—
—S—


A-73
CH
CH
3
4
H
Ph
—O—
—OCH2


A-74
CH
CH
3
4
H
Ph
—O—
singlebond


A-75
CH
CH
3
4
H
Ph
—S—
—O—


A-76
CH
CH
3
4
H
Ph
—CH2O—
—O—


A-77
CH
CH
3
4
H
Ph
singlebond
—O—


A-78
CH
CH
3
4
H
Ph
—S—
—S—


A-79
CH
CH
3
4
H
Ph
—CH2O—
—OCH2


A-80
CH
CH
3
4
H
Ph
singlebond
singlebond


A-81
CH
CH
4
3
Me
H
—O—
—O—


A-82
CH
CH
4
3
Me
H
—O—
—S—


A-83
CH
CH
4
3
Me
H
—O—
—OCH2


A-84
CH
CH
4
3
Me
H
—O—
singlebond


A-85
CH
CH
4
3
Me
H
—S—
—O—


A-86
CH
CH
4
3
Me
H
—CH2O—
—O—


A-87
CH
CH
4
3
Me
H
singlebond
—O—


A-88
CH
CH
4
3
Me
H
—S—
—S—


A-89
CH
CH
4
3
Me
H
—CH2O—
—OCH2


A-90
CH
CH
4
3
Me
H
singlebond
singlebond


A-91
CH
CH
4
3
H
Me
—O—
—O—


A-92
CH
CH
4
3
H
Me
—O—
—S—


A-93
CH
CH
4
3
H
Me
—O—
—OCH2


A-94
CH
CH
4
3
H
Me
—O—
singlebond


A-95
CH
CH
4
3
H
Me
—S—
—O—


A-96
CH
CH
4
3
H
Me
—CH2O—
—O—


A-97
CH
CH
4
3
H
Me
singlebond
—O—


A-98
CH
CH
4
3
H
Me
—S—
—S—


A-99
CH
CH
4
3
H
Me
—CH2O—
—OCH2


A-100
CH
CH
4
3
H
Me
singlebond
singlebond


A-101
CH
CH
4
3
Ph
H
—O—
—O—


A-102
CH
CH
4
3
Ph
H
—O—
—S—


A-103
CH
CH
4
3
Ph
H
—O—
—OCH2


A-104
CH
CH
4
3
Ph
H
—O—
singlebond


A-105
CH
CH
4
3
Ph
H
—S—
—O—


A-106
CH
CH
4
3
Ph
H
—CH2O—
—O—


A-107
CH
CH
4
3
Ph
H
singlebond
—O—


A-108
CH
CH
4
3
Ph
H
—S—
—S—


A-109
CH
CH
4
3
Ph
H
—CH2O—
—OCH2


A-110
CH
CH
4
3
Ph
H
singlebond
singlebond
























TABLE 2





Compound










No.
G1
G2
n
m
Ra
Rc
Q1
Q2







A-111
CH
CH
4
3
H
Ph
—O—
—O—


A-112
CH
CH
4
3
H
Ph
—O—
—S—


A-113
CH
CH
4
3
H
Ph
—O—
—OCH2


A-114
CH
CH
4
3
H
Ph
—O—
singlebond


A-115
CH
CH
4
3
H
Ph
—S—
—O—


A-116
CH
CH
4
3
H
Ph
—CH2O—
—O—


A-117
CH
CH
4
3
H
Ph
singlebond
—O—


A-118
CH
CH
4
3
H
Ph
—S—
—S—


A-119
CH
CH
4
3
H
Ph
—CH2O—
—OCH2


A-120
CH
CH
4
3
H
Ph
singlebond
singlebond


A-121
CH
CH
4
4
Me
H
—O—
—O—


A-122
CH
CH
4
4
Me
H
—O—
—S—


A-123
CH
CH
4
4
Me
H
—O—
—OCH2


A-124
CH
CH
4
4
Me
H
—O—
singlebond


A-125
CH
CH
4
4
Me
H
—S—
—O—


A-126
CH
CH
4
4
Me
H
—CH2O—
—O—


A-127
CH
CH
4
4
Me
H
singlebond
—O—


A-128
CH
CH
4
4
Me
H
—S—
—S—


A-129
CH
CH
4
4
Me
H
—CH2O—
—OCH2


A-130
CH
CH
4
4
Me
H
singlebond
singlebond


A-131
CH
CH
4
4
H
Me
—O—
—O—


A-132
CH
CH
4
4
H
Me
—O—
—S—


A-133
CH
CH
4
4
H
Me
—O—
—OCH2


A-134
CH
CH
4
4
H
Me
—O—
singlebond


A-135
CH
CH
4
4
H
Me
—S—
—O—


A-136
CH
CH
4
4
H
Me
—CH2O—
—O—


A-137
CH
CH
4
4
H
Me
singlebond
—O—


A-138
CH
CH
4
4
H
Me
—S—
—S—


A-139
CH
CH
4
4
H
Me
—CH2O—
—OCH2


A-140
CH
CH
4
4
H
Me
singlebond
singlebond


A-141
CH
CH
4
4
Ph
H
—O—
—O—


A-142
CH
CH
4
4
Ph
H
—O—
—S—


A-143
CH
CH
4
4
Ph
H
—O—
—OCH2


A-144
CH
CH
4
4
Ph
H
—O—
singlebond


A-145
CH
CH
4
4
Ph
H
—S—
—O—


A-146
CH
CH
4
4
Ph
H
—CH2O—
—O—


A-147
CH
CH
4
4
Ph
H
singlebond
—O—


A-148
CH
CH
4
4
Ph
H
—S—
—S—


A-149
CH
CH
4
4
Ph
H
—CH2O—
—OCH2


A-150
CH
CH
4
4
Ph
H
singlebond
singlebond


A-151
CH
CH
4
4
H
Ph
—O—
—O—


A-152
CH
CH
4
4
H
Ph
—O—
—S—


A-153
CH
CH
4
4
H
Ph
—O—
—OCH2


A-154
CH
CH
4
4
H
Ph
—O—
singlebond


A-155
CH
CH
4
4
H
Ph
—S—
—O—


A-156
CH
CH
4
4
H
Ph
—CH2O—
—O—


A-157
CH
CH
4
4
H
Ph
singlebond
—O—


A-158
CH
CH
4
4
H
Ph
—S—
—S—


A-159
CH
CH
4
4
H
Ph
—CH2O—
—OCH2


A-160
CH
CH
4
4
H
Ph
singlebond
singlebond


A-161
N
CH
3
3
Me
H
—O—
—O—


A-162
N
CH
3
3
Me
H
—O—
—S—


A-163
N
CH
3
3
Me
H
—O—
—OCH2


A-164
N
CH
3
3
Me
H
—O—
singlebond


A-165
N
CH
3
3
Me
H
—S—
—O—


A-166
N
CH
3
3
Me
H
—CH2O—
—O—


A-167
N
CH
3
3
Me
H
singlebond
—O—


A-168
N
CH
3
3
Me
H
—S—
—S—


A-169
N
CH
3
3
Me
H
—CH2O—
—OCH2


A-170
N
CH
3
3
Me
H
singlebond
singlebond


A-171
N
CH
3
3
H
Me
—O—
—O—


A-172
N
CH
3
3
H
Me
—O—
—S—


A-173
N
CH
3
3
H
Me
—O—
—OCH2


A-174
N
CH
3
3
H
Me
—O—
singlebond


A-175
N
CH
3
3
H
Me
—S—
—O—


A-176
N
CH
3
3
H
Me
—CH2O—
—O—


A-177
N
CH
3
3
H
Me
singlebond
—O—


A-178
N
CH
3
3
H
Me
—S—
—S—


A-179
N
CH
3
3
H
Me
—CH2O—
—OCH2


A-180
N
CH
3
3
H
Me
singlebond
singlebond


A-181
N
CH
3
3
Ph
H
—O—
—O—


A-182
N
CH
3
3
Ph
H
—O—
—S—


A-183
N
CH
3
3
Ph
H
—O—
—OCH2


A-184
N
CH
3
3
Ph
H
—O—
singlebond


A-185
N
CH
3
3
Ph
H
—S—
—O—


A-186
N
CH
3
3
Ph
H
—CH2O—
—O—


A-187
N
CH
3
3
Ph
H
singlebond
—O—


A-188
N
CH
3
3
Ph
H
—S—
—S—


A-189
N
CH
3
3
Ph
H
—CH2O—
—OCH2


A-190
N
CH
3
3
Ph
H
singlebond
singlebond


A-191
N
CH
3
3
H
Ph
—O—
—O—


A-192
N
CH
3
3
H
Ph
—O—
—S—


A-193
N
CH
3
3
H
Ph
—O—
—OCH2


A-194
N
CH
3
3
H
Ph
—O—
singlebond


A-195
N
CH
3
3
H
Ph
—S—
—O—


A-196
N
CH
3
3
H
Ph
—CH2O—
—O—


A-197
N
CH
3
3
H
Ph
singlebond
—O—


A-198
N
CH
3
3
H
Ph
—S—
—S—


A-199
N
CH
3
3
H
Ph
—CH2O—
—OCH2


A-200
N
CH
3
3
H
Ph
singlebond
singlebond


A-201
N
CH
3
4
Me
H
—O—
—O—


A-202
N
CH
3
4
Me
H
—O—
—S—


A-203
N
CH
3
4
Me
H
—O—
—OCH2


A-204
N
CH
3
4
Me
H
—O—
singlebond


A-205
N
CH
3
4
Me
H
—S—
—O—


A-206
N
CH
3
4
Me
H
—CH2O—
—O—


A-207
N
CH
3
4
Me
H
singlebond
—O—


A-208
N
CH
3
4
Me
H
—S—
—S—


A-209
N
CH
3
4
Me
H
—CH2O—
—OCH2


A-210
N
CH
3
4
Me
H
singlebond
singlebond


A-211
N
CH
3
4
H
Me
—O—
—O—


A-212
N
CH
3
4
H
Me
—O—
—S—


A-213
N
CH
3
4
H
Me
—O—
—OCH2


A-214
N
CH
3
4
H
Me
—O—
singlebond


A-215
N
CH
3
4
H
Me
—S—
—O—


A-216
N
CH
3
4
H
Me
—CH2O—
—O—


A-217
N
CH
3
4
H
Me
singlebond
—O—


A-218
N
CH
3
4
H
Me
—S—
—S—


A-219
N
CH
3
4
H
Me
—CH2O—
—OCH2


A-220
N
CH
3
4
H
Me
singlebond
singlebond
























TABLE 3





Compound










No.
G1
G2
n
m
Ra
Rc
Q1
Q2







A-221
N
CH
3
4
Ph
H
—O—
—O—


A-222
N
CH
3
4
Ph
H
—O—
—S—


A-223
N
CH
3
4
Ph
H
—O—
—OCH2


A-224
N
CH
3
4
Ph
H
—O—
singlebond


A-225
N
CH
3
4
Ph
H
—S—
—O—


A-226
N
CH
3
4
Ph
H
—CH2O—
—O—


A-227
N
CH
3
4
Ph
H
singlebond
—O—


A-228
N
CH
3
4
Ph
H
—S—
—S—


A-229
N
CH
3
4
Ph
H
—CH2O—
—OCH2


A-230
N
CH
3
4
Ph
H
singlebond
singlebond


A-231
N
CH
3
4
H
Ph
—O—
—O—


A-232
N
CH
3
4
H
Ph
—O—
—S—


A-233
N
CH
3
4
H
Ph
—O—
—OCH2


A-234
N
CH
3
4
H
Ph
—O—
singlebond


A-235
N
CH
3
4
H
Ph
—S—
—O—


A-236
N
CH
3
4
H
Ph
—CH2O—
—O—


A-237
N
CH
3
4
H
Ph
singlebond
—O—


A-238
N
CH
3
4
H
Ph
—S—
—S—


A-239
N
CH
3
4
H
Ph
—CH2O—
—OCH2


A-240
N
CH
3
4
H
Ph
singlebond
singlebond


A-241
N
CH
4
3
Me
H
—O—
—O—


A-242
N
CH
4
3
Me
H
—O—
—S—


A-243
N
CH
4
3
Me
H
—O—
—OCH2


A-244
N
CH
4
3
Me
H
—O—
singlebond


A-245
N
CH
4
3
Me
H
—S—
—O—


A-246
N
CH
4
3
Me
H
—CH2O—
—O—


A-247
N
CH
4
3
Me
H
singlebond
—O—


A-248
N
CH
4
3
Me
H
—S—
—S—


A-249
N
CH
4
3
Me
H
—CH2O—
—OCH2


A-250
N
CH
4
3
Me
H
singlebond
singlebond


A-251
N
CH
4
3
H
Me
—O—
—O—


A-252
N
CH
4
3
H
Me
—O—
—S—


A-253
N
CH
4
3
H
Me
—O—
—OCH2


A-254
N
CH
4
3
H
Me
—O—
singlebond


A-255
N
CH
4
3
H
Me
—S—
—O—


A-256
N
CH
4
3
H
Me
—CH2O—
—O—


A-257
N
CH
4
3
H
Me
singlebond
—O—


A-258
N
CH
4
3
H
Me
—S—
—S—


A-259
N
CH
4
3
H
Me
—CH2O—
—OCH2


A-260
N
CH
4
3
H
Me
singlebond
singlebond


A-261
N
CH
4
3
Ph
H
—O—
—O—


A-262
N
CH
4
3
Ph
H
—O—
—S—


A-263
N
CH
4
3
Ph
H
—O—
—OCH2


A-264
N
CH
4
3
Ph
H
—O—
singlebond


A-265
N
CH
4
3
Ph
H
—S—
—O—


A-266
N
CH
4
3
Ph
H
—CH2O—
—O—


A-267
N
CH
4
3
Ph
H
singlebond
—O—


A-268
N
CH
4
3
Ph
H
—S—
—S—


A-269
N
CH
4
3
Ph
H
—CH2O—
—OCH2


A-270
N
CH
4
3
Ph
H
singlebond
singlebond


A-271
N
CH
4
3
H
Ph
—O—
—O—


A-272
N
CH
4
3
H
Ph
—O—
—S—


A-273
N
CH
4
3
H
Ph
—O—
—OCH2


A-274
N
CH
4
3
H
Ph
—O—
singlebond


A-275
N
CH
4
3
H
Ph
—S—
—O—


A-276
N
CH
4
3
H
Ph
—CH2O—
—O—


A-277
N
CH
4
3
H
Ph
singlebond
—O—


A-278
N
CH
4
3
H
Ph
—S—
—S—


A-279
N
CH
4
3
H
Ph
—CH2O—
—OCH2


A-280
N
CH
4
3
H
Ph
singlebond
singlebond


A-281
N
CH
4
4
Me
H
—O—
—O—


A-282
N
CH
4
4
Me
H
—O—
—S—


A-283
N
CH
4
4
Me
H
—O—
—OCH2


A-284
N
CH
4
4
Me
H
—O—
singlebond


A-285
N
CH
4
4
Me
H
—S—
—O—


A-286
N
CH
4
4
Me
H
—CH2O—
—O—


A-287
N
CH
4
4
Me
H
singlebond
—O—


A-288
N
CH
4
4
Me
H
—S—
—S—


A-289
N
CH
4
4
Me
H
—CH2O—
—OCH2


A-290
N
CH
4
4
Me
H
singlebond
singlebond


A-291
N
CH
4
4
H
Me
—O—
—O—


A-292
N
CH
4
4
H
Me
—O—
—S—


A-293
N
CH
4
4
H
Me
—O—
—OCH2


A-294
N
CH
4
4
H
Me
—O—
singlebond


A-295
N
CH
4
4
H
Me
—S—
—O—


A-296
N
CH
4
4
H
Me
—CH2O—
—O—


A-297
N
CH
4
4
H
Me
singlebond
—O—


A-298
N
CH
4
4
H
Me
—S—
—S—


A-299
N
CH
4
4
H
Me
—CH2O—
—OCH2


A-300
N
CH
4
4
H
Me
singlebond
singlebond


A-301
N
CH
4
4
Ph
H
—O—
—O—


A-302
N
CH
4
4
Ph
H
—O—
—S—


A-303
N
CH
4
4
Ph
H
—O—
—OCH2


A-304
N
CH
4
4
Ph
H
—O—
singlebond


A-305
N
CH
4
4
Ph
H
—S—
—O—


A-306
N
CH
4
4
Ph
H
—CH2O—
—O—


A-307
N
CH
4
4
Ph
H
singlebond
—O—


A-308
N
CH
4
4
Ph
H
—S—
—S—


A-309
N
CH
4
4
Ph
H
—CH2O—
—OCH2


A-310
N
CH
4
4
Ph
H
singlebond
singlebond


A-311
N
CH
4
4
H
Ph
—O—
—O—


A-312
N
CH
4
4
H
Ph
—O—
—S—


A-313
N
CH
4
4
H
Ph
—O—
—OCH2


A-314
N
CH
4
4
H
Ph
—O—
singlebond


A-315
N
CH
4
4
H
Ph
—S—
—O—


A-316
N
CH
4
4
H
Ph
—CH2O—
—O—


A-317
N
CH
4
4
H
Ph
singlebond
—O—


A-318
N
CH
4
4
H
Ph
—S—
—S—


A-319
N
CH
4
4
H
Ph
—CH2O—
—OCH2


A-320
N
CH
4
4
H
Ph
singlebond
singlebond


A-321
CH
N
3
3
Me
H
—O—
—O—


A-322
CH
N
3
3
Me
H
—O—
—S—


A-323
CH
N
3
3
Me
H
—O—
—OCH2


A-324
CH
N
3
3
Me
H
—O—
singlebond


A-325
CH
N
3
3
Me
H
—S—
—O—


A-326
CH
N
3
3
Me
H
—CH2O—
—O—


A-327
CH
N
3
3
Me
H
singlebond
—O—


A-328
CH
N
3
3
Me
H
—S—
—S—


A-329
CH
N
3
3
Me
H
—CH2O—
—OCH2


A-330
CH
N
3
3
Me
H
singlebond
singlebond
























TABLE 4





Compound










No.
G1
G2
n
m
Ra
Rc
Q1
Q2







A-331
CH
N
3
3
H
Me
—O—
—O—


A-332
CH
N
3
3
H
Me
—O—
—S—


A-333
CH
N
3
3
H
Me
—O—
—OCH2


A-334
CH
N
3
3
H
Me
—O—
singlebond


A-335
CH
N
3
3
H
Me
—S—
—O—


A-336
CH
N
3
3
H
Me
—CH2O—
—O—


A-337
CH
N
3
3
H
Me
singlebond
—O—


A-338
CH
N
3
3
H
Me
—S—
—S—


A-339
CH
N
3
3
H
Me
—CH2O—
—OCH2


A-340
CH
N
3
3
H
Me
singlebond
singlebond


A-341
CH
N
3
3
Ph
H
—O—
—O—


A-342
CH
N
3
3
Ph
H
—O—
—S—


A-343
CH
N
3
3
Ph
H
—O—
—OCH2


A-344
CH
N
3
3
Ph
H
—O—
singlebond


A-345
CH
N
3
3
Ph
H
—S—
—O—


A-346
CH
N
3
3
Ph
H
—CH2O—
—O—


A-347
CH
N
3
3
Ph
H
singlebond
—O—


A-348
CH
N
3
3
Ph
H
—S—
—S—


A-349
CH
N
3
3
Ph
H
—CH2O—
—OCH2


A-350
CH
N
3
3
Ph
H
singlebond
singlebond


A-351
CH
N
3
3
H
Ph
—O—
—O—


A-352
CH
N
3
3
H
Ph
—O—
—S—


A-353
CH
N
3
3
H
Ph
—O—
—OCH2


A-354
CH
N
3
3
H
Ph
—O—
singlebond


A-355
CH
N
3
3
H
Ph
—S—
—O—


A-356
CH
N
3
3
H
Ph
—CH2O—
—O—


A-357
CH
N
3
3
H
Ph
singlebond
—O—


A-358
CH
N
3
3
H
Ph
—S—
—S—


A-359
CH
N
3
3
H
Ph
—CH2O—
—OCH2


A-360
CH
N
3
3
H
Ph
singlebond
singlebond


A-361
CH
N
3
4
Me
H
—O—
—O—


A-362
CH
N
3
4
Me
H
—O—
—S—


A-363
CH
N
3
4
Me
H
—O—
—OCH2


A-364
CH
N
3
4
Me
H
—O—
singlebond


A-365
CH
N
3
4
Me
H
—S—
—O—


A-366
CH
N
3
4
Me
H
—CH2O—
—O—


A-367
CH
N
3
4
Me
H
singlebond
—O—


A-368
CH
N
3
4
Me
H
—S—
—S—


A-369
CH
N
3
4
Me
H
—CH2O—
—OCH2


A-370
CH
N
3
4
Me
H
singlebond
singlebond


A-371
CH
N
3
4
H
Me
—O—
—O—


A-372
CH
N
3
4
H
Me
—O—
—S—


A-373
CH
N
3
4
H
Me
—O—
—OCH2


A-374
CH
N
3
4
H
Me
—O—
singlebond


A-375
CH
N
3
4
H
Me
—S—
—O—


A-376
CH
N
3
4
H
Me
—CH2O—
—O—


A-377
CH
N
3
4
H
Me
singlebond
—O—


A-378
CH
N
3
4
H
Me
—S—
—S—


A-379
CH
N
3
4
H
Me
—CH2O—
—OCH2


A-380
CH
N
3
4
H
Me
singlebond
singlebond


A-381
CH
N
3
4
Ph
H
—O—
—O—


A-382
CH
N
3
4
Ph
H
—O—
—S—


A-383
CH
N
3
4
Ph
H
—O—
—OCH2


A-384
CH
N
3
4
Ph
H
—O—
singlebond


A-385
CH
N
3
4
Ph
H
—S—
—O—


A-386
CH
N
3
4
Ph
H
—CH2O—
—O—


A-387
CH
N
3
4
Ph
H
singlebond
—O—


A-388
CH
N
3
4
Ph
H
—S—
—S—


A-389
CH
N
3
4
Ph
H
—CH2O—
—OCH2


A-390
CH
N
3
4
Ph
H
singlebond
singlebond


A-391
CH
N
3
4
H
Ph
—O—
—O—


A-392
CH
N
3
4
H
Ph
—O—
—S—


A-393
CH
N
3
4
H
Ph
—O—
—OCH2


A-394
CH
N
3
4
H
Ph
—O—
singlebond


A-395
CH
N
3
4
H
Ph
—S—
—O—


A-396
CH
N
3
4
H
Ph
—CH2O—
—O—


A-397
CH
N
3
4
H
Ph
singlebond
—O—


A-398
CH
N
3
4
H
Ph
—S—
—S—


A-399
CH
N
3
4
H
Ph
—CH2O—
—OCH2


A-400
CH
N
3
4
H
Ph
singlebond
singlebond


A-401
CH
N
4
3
Me
H
—O—
—O—


A-402
CH
N
4
3
Me
H
—O—
—S—


A-403
CH
N
4
3
Me
H
—O—
—OCH2


A-404
CH
N
4
3
Me
H
—O—
singlebond


A-405
CH
N
4
3
Me
H
—S—
—O—


A-406
CH
N
4
3
Me
H
—CH2O—
—O—


A-407
CH
N
4
3
Me
H
singlebond
—O—


A-408
CH
N
4
3
Me
H
—S—
—S—


A-409
CH
N
4
3
Me
H
—CH2O—
—OCH2


A-410
CH
N
4
3
Me
H
singlebond
singlebond


A-411
CH
N
4
3
H
Me
—O—
—O—


A-412
CH
N
4
3
H
Me
—O—
—S—


A-413
CH
N
4
3
H
Me
—O—
—OCH2


A-414
CH
N
4
3
H
Me
—O—
singlebond


A-415
CH
N
4
3
H
Me
—S—
—O—


A-416
CH
N
4
3
H
Me
—CH2O—
—O—


A-417
CH
N
4
3
H
Me
singlebond
—O—


A-418
CH
N
4
3
H
Me
—S—
—S—


A-419
CH
N
4
3
H
Me
—CH2O—
—OCH2


A-420
CH
N
4
3
H
Me
singlebond
singlebond


A-421
CH
N
4
3
Ph
H
—O—
—O—


A-422
CH
N
4
3
Ph
H
—O—
—S—


A-423
CH
N
4
3
Ph
H
—O—
—OCH2


A-424
CH
N
4
3
Ph
H
—O—
singlebond


A-425
CH
N
4
3
Ph
H
—S—
—O—


A-426
CH
N
4
3
Ph
H
—CH2O—
—O—


A-427
CH
N
4
3
Ph
H
singlebond
—O—


A-428
CH
N
4
3
Ph
H
—S—
—S—


A-429
CH
N
4
3
Ph
H
—CH2O—
—OCH2


A-430
CH
N
4
3
Ph
H
singlebond
singlebond


A-431
CH
N
4
3
H
Ph
—O—
—O—


A-432
CH
N
4
3
H
Ph
—O—
—S—


A-433
CH
N
4
3
H
Ph
—O—
—OCH2


A-434
CH
N
4
3
H
Ph
—O—
singlebond


A-435
CH
N
4
3
H
Ph
—S—
—O—


A-436
CH
N
4
3
H
Ph
—CH2O—
—O—


A-437
CH
N
4
3
H
Ph
singlebond
—O—


A-438
CH
N
4
3
H
Ph
—S—
—S—


A-439
CH
N
4
3
H
Ph
—CH2O—
—OCH2


A-440
CH
N
4
3
H
Ph
singlebond
singlebond
























TABLE 5





Compound










No.
G1
G2
n
m
Ra
Rc
Q1
Q2







A-441
CH
N
4
4
Me
H
—O—
—O—


A-442
CH
N
4
4
Me
H
—O—
—S—


A-443
CH
N
4
4
Me
H
—O—
—OCH2


A-444
CH
N
4
4
Me
H
—O—
singlebond


A-445
CH
N
4
4
Me
H
—S—
—O—


A-446
CH
N
4
4
Me
H
—CH2O—
—O—


A-447
CH
N
4
4
Me
H

—O—


A-448
CH
N
4
4
Me
H
—S—
—S—


A-449
CH
N
4
4
Me
H
—CH2O—
—OCH2


A-450
CH
N
4
4
Me
H
singlebond
singlebond


A-451
CH
N
4
4
H
Me
—O—
—O—


A-452
CH
N
4
4
H
Me
—O—
—S—


A-453
CH
N
4
4
H
Me
—O—
—OCH2


A-454
CH
N
4
4
H
Me
—O—
singlebond


A-455
CH
N
4
4
H
Me
—S—
—O—


A-456
CH
N
4
4
H
Me
—CH2O—
—O—


A-457
CH
N
4
4
H
Me
singlebond
—O—


A-458
CH
N
4
4
H
Me
—S—
—S—


A-459
CH
N
4
4
H
Me
—CH2O—
—OCH2


A-460
CH
N
4
4
H
Me
singlebond
singlebond


A-461
CH
N
4
4
Ph
H
—O—
—O—


A-462
CH
N
4
4
Ph
H
—O—
—S—


A-463
CH
N
4
4
Ph
H
—O—
—OCH2


A-464
CH
N
4
4
Ph
H
—O—
singlebond


A-465
CH
N
4
4
Ph
H
—S—
—O—


A-466
CH
N
4
4
Ph
H
—CH2O—
—O—


A-467
CH
N
4
4
Ph
H
singlebond
—O—


A-468
CH
N
4
4
Ph
H
—S—
—S—


A-469
CH
N
4
4
Ph
H
—CH2O—
—OCH2


A-470
CH
N
4
4
Ph
H
singlebond
singlebond


A-471
CH
N
4
4
H
Ph
—O—
—O—


A-472
CH
N
4
4
H
Ph
—O—
—S—


A-473
CH
N
4
4
H
Ph
—O—
—OCH2


A-474
CH
N
4
4
H
Ph
—O—
singlebond


A-475
CH
N
4
4
H
Ph
—S—
—O—


A-476
CH
N
4
4
H
Ph
—CH2O—
—O—


A-477
CH
N
4
4
H
Ph
singlebond
—O—


A-478
CH
N
4
4
H
Ph
—S—
—S—


A-479
CH
N
4
4
H
Ph
—CH2O—
—OCH2


A-480
CH
N
4
4
H
Ph
singlebond
singlebond


A-481
CH
CH
2
5
H
H
—O—
—O—


A-482
CH
CH
3
5
H
H
—O—
—O—


A-483
CH
CH
5
2
H
H
—O—
—O—


A-484
CH
CH
5
3
H
H
—O—
—O—











embedded image

















TABLE 6





Compound










No.
G1
G2
n
m
Ra
Rc
Q1
Q2







B-1
CH
CH
3
3
Me
H
—O—
—O—


B-2
CH
CH
3
3
Me
H
—O—
—S—


B-3
CH
CH
3
3
Me
H
—O—
—OCH2


B-4
CH
CH
3
3
Me
H
—O—
singlebond


B-5
CH
CH
3
3
Me
H
—S—
—O—


B-6
CH
CH
3
3
Me
H
—CH2O—
—O—


B-7
CH
CH
3
3
Me
H
singlebond
—O—


B-8
CH
CH
3
3
Me
H
—S—
—S—


B-9
CH
CH
3
3
Me
H
—CH2O—
—OCH2


B-10
CH
CH
3
3
Me
H
singlebond
singlebond


B-11
CH
CH
3
3
H
Me
—O—
—O—


B-12
CH
CH
3
3
H
Me
—O—
—S—


B-13
CH
CH
3
3
H
Me
—O—
—OCH2


B-14
CH
CH
3
3
H
Me
—O—
singlebond


B-15
CH
CH
3
3
H
Me
—S—
—O—


B-16
CH
CH
3
3
H
Me
—CH2O—
—O—


B-17
CH
CH
3
3
H
Me
singlebond
—O—


B-18
CH
CH
3
3
H
Me
—S—
—S—


B-19
CH
CH
3
3
H
Me
—CH2O—
—OCH2


B-20
CH
CH
3
3
H
Me
singlebond
singlebond


B-21
CH
CH
3
3
Ph
H
—O—
—O—


B-22
CH
CH
3
3
Ph
H
—O—
—S—


B-23
CH
CH
3
3
Ph
H
—O—
—OCH2


B-24
CH
CH
3
3
Ph
H
—O—
singlebond


B-25
CH
CH
3
3
Ph
H
—S—
—O—


B-26
CH
CH
3
3
Ph
H
—CH2O—
—O—


B-27
CH
CH
3
3
Ph
H
singlebond
—O—


B-28
CH
CH
3
3
Ph
H
—S—
—S—


B-29
CH
CH
3
3
Ph
H
—CH2O—
—OCH2


B-30
CH
CH
3
3
Ph
H
singlebond
singlebond


B-31
CH
CH
3
3
H
Ph
—O—
—O—


B-32
CH
CH
3
3
H
Ph
—O—
—S—


B-33
CH
CH
3
3
H
Ph
—O—
—OCH2


B-34
CH
CH
3
3
H
Ph
—O—
singlebond


B-35
CH
CH
3
3
H
Ph
—S—
—O—


B-36
CH
CH
3
3
H
Ph
—CH2O—
—O—


B-37
CH
CH
3
3
H
Ph
singlebond
—O—


B-38
CH
CH
3
3
H
Ph
—S—
—S—


B-39
CH
CH
3
3
H
Ph
—CH2O—
—OCH2


B-40
CH
CH
3
3
H
Ph
singlebond
singlebond


B-41
CH
CH
3
4
Me
H
—O—
—O—


B-42
CH
CH
3
4
Me
H
—O—
—S—


B-43
CH
CH
3
4
Me
H
—O—
—OCH2


B-44
CH
CH
3
4
Me
H
—O—
singlebond


B-45
CH
CH
3
4
Me
H
—S—
—O—


B-46
CH
CH
3
4
Me
H
—CH2O—
—O—


B-47
CH
CH
3
4
Me
H
singlebond
—O—


B-48
CH
CH
3
4
Me
H
—S—
—S—


B-49
CH
CH
3
4
Me
H
—CH2O—
—OCH2


B-50
CH
CH
3
4
Me
H
singlebond
singlebond


B-51
CH
CH
3
4
H
Me
—O—
—O—


B-52
CH
CH
3
4
H
Me
—O—
—S—


B-53
CH
CH
3
4
H
Me
—O—
—OCH2


B-54
CH
CH
3
4
H
Me
—O—
singlebond


B-55
CH
CH
3
4
H
Me
—S—
—O—


B-56
CH
CH
3
4
H
Me
—CH2O—
—O—


B-57
CH
CH
3
4
H
Me
singlebond
—O—


B-58
CH
CH
3
4
H
Me
—S—
—S—


B-59
CH
CH
3
4
H
Me
—CH2O—
—OCH2


B-60
CH
CH
3
4
H
Me
singlebond
singlebond


B-61
CH
CH
3
4
Ph
H
—O—
—O—


B-62
CH
CH
3
4
Ph
H
—O—
—S—


B-63
CH
CH
3
4
Ph
H
—O—
—OCH2


B-64
CH
CH
3
4
Ph
H
—O—
singlebond


B-65
CH
CH
3
4
Ph
H
—S—
—O—


B-66
CH
CH
3
4
Ph
H
—CH2O—
—O—


B-67
CH
CH
3
4
Ph
H
singlebond
—O—


B-68
CH
CH
3
4
Ph
H
—S—
—S—


B-69
CH
CH
3
4
Ph
H
—CH2O—
—OCH2


B-70
CH
CH
3
4
Ph
H
singlebond
singlebond


B-71
CH
CH
3
4
H
Ph
—O—
—O—


B-72
CH
CH
3
4
H
Ph
—O—
—S—


B-73
CH
CH
3
4
H
Ph
—O—
—OCH2


B-74
CH
CH
3
4
H
Ph
—O—
singlebond


B-75
CH
CH
3
4
H
Ph
—S—
—O—


B-76
CH
CH
3
4
H
Ph
—CH2O—
—O—


B-77
CH
CH
3
4
H
Ph
singlebond
—O—


B-78
CH
CH
3
4
H
Ph
—S—
—S—


B-79
CH
CH
3
4
H
Ph
—CH2O—
—OCH2


B-80
CH
CH
3
4
H
Ph
singlebond
singlebond


B-81
CH
CH
4
3
Me
H
—O—
—O—


B-82
CH
CH
4
3
Me
H
—O—
—S—


B-83
CH
CH
4
3
Me
H
—O—
—OCH2


B-84
CH
CH
4
3
Me
H
—O—
singlebond


B-85
CH
CH
4
3
Me
H
—S—
—O—


B-86
CH
CH
4
3
Me
H
—CH2O—
—O—


B-87
CH
CH
4
3
Me
H
singlebond
—O—


B-88
CH
CH
4
3
Me
H
—S—
—S—


B-89
CH
CH
4
3
Me
H
—CH2O—
—OCH2


B-90
CH
CH
4
3
Me
H
singlebond
singlebond


B-91
CH
CH
4
3
H
Me
—O—
—O—


B-92
CH
CH
4
3
H
Me
—O—
—S—


B-93
CH
CH
4
3
H
Me
—O—
—OCH2


B-94
CH
CH
4
3
H
Me
—O—
singlebond


B-95
CH
CH
4
3
H
Me
—S—
—O—


B-96
CH
CH
4
3
H
Me
—CH2O—
—O—


B-97
CH
CH
4
3
H
Me
singlebond
—O—


B-98
CH
CH
4
3
H
Me
—S—
—S—


B-99
CH
CH
4
3
H
Me
—CH2O—
—OCH2


B-100
CH
CH
4
3
H
Me
singlebond
singlebond


B-101
CH
CH
4
3
Ph
H
—O—
—O—


B-102
CH
CH
4
3
Ph
H
—O—
—S—


B-103
CH
CH
4
3
Ph
H
—O—
—OCH2


B-104
CH
CH
4
3
Ph
H
—O—
singlebond


B-105
CH
CH
4
3
Ph
H
—S—
—O—


B-106
CH
CH
4
3
Ph
H
—CH2O—
—O—


B-107
CH
CH
4
3
Ph
H
singlebond
—O—


B-108
CH
CH
4
3
Ph
H
—S—
—S—


B-109
CH
CH
4
3
Ph
H
—CH2O—
—OCH2


B-110
CH
CH
4
3
Ph
H
singlebond
singlebond
























TABLE 7





Compound










No.
G1
G2
n
m
Ra
Rc
Q1
Q2







B-111
CH
CH
4
3
H
Ph
—O—
—O—


B-112
CH
CH
4
3
H
Ph
—O—
—S—


B-113
CH
CH
4
3
H
Ph
—O—
—OCH2


B-114
CH
CH
4
3
H
Ph
—O—
singlebond


B-115
CH
CH
4
3
H
Ph
—S—
—O—


B-116
CH
CH
4
3
H
Ph
—CH2O—
—O—


B-117
CH
CH
4
3
H
Ph
singlebond
—O—


B-118
CH
CH
4
3
H
Ph
—S—
—S—


B-119
CH
CH
4
3
H
Ph
—CH2O—
—OCH2


B-120
CH
CH
4
3
H
Ph
singlebond
singlebond


B-121
CH
CH
4
4
Me
H
—O—
—O—


B-122
CH
CH
4
4
Me
H
—O—
—S—


B-123
CH
CH
4
4
Me
H
—O—
—OCH2


B-124
CH
CH
4
4
Me
H
—O—
singlebond


B-125
CH
CH
4
4
Me
H
—S—
—O—


B-126
CH
CH
4
4
Me
H
—CH2O—
—O—


B-127
CH
CH
4
4
Me
H
singlebond
—O—


B-128
CH
CH
4
4
Me
H
—S—
—S—


B-129
CH
CH
4
4
Me
H
—CH2O—
—OCH2


B-130
CH
CH
4
4
Me
H
singlebond
singlebond


B-131
CH
CH
4
4
H
Me
—O—
—O—


B-132
CH
CH
4
4
H
Me
—O—
—S—


B-133
CH
CH
4
4
H
Me
—O—
—OCH2


B-134
CH
CH
4
4
H
Me
—O—
singlebond


B-135
CH
CH
4
4
H
Me
—S—
—O—


B-136
CH
CH
4
4
H
Me
—CH2O—
—O—


B-137
CH
CH
4
4
H
Me
singlebond
—O—


B-138
CH
CH
4
4
H
Me
—S—
—S—


B-139
CH
CH
4
4
H
Me
—CH2O—
—OCH2


B-140
CH
CH
4
4
H
Me
singlebond
singlebond


B-141
CH
CH
4
4
Ph
H
—O—
—O—


B-142
CH
CH
4
4
Ph
H
—O—
—S—


B-143
CH
CH
4
4
Ph
H
—O—
—OCH2


B-144
CH
CH
4
4
Ph
H
—O—
singlebond


B-145
CH
CH
4
4
Ph
H
—S—
—O—


B-146
CH
CH
4
4
Ph
H
—CH2O—
—O—


B-147
CH
CH
4
4
Ph
H
singlebond
—O—


B-148
CH
CH
4
4
Ph
H
—S—
—S—


B-149
CH
CH
4
4
Ph
H
—CH2O—
—OCH2


B-150
CH
CH
4
4
Ph
H
singlebond
singlebond


B-151
CH
CH
4
4
H
Ph
—O—
—O—


B-152
CH
CH
4
4
H
Ph
—O—
—S—


B-153
CH
CH
4
4
H
Ph
—O—
—OCH2


B-154
CH
CH
4
4
H
Ph
—O—
singlebond


B-155
CH
CH
4
4
H
Ph
—S—
—O—


B-156
CH
CH
4
4
H
Ph
—CH2O—
—O—


B-157
CH
CH
4
4
H
Ph
singlebond
—O—


B-158
CH
CH
4
4
H
Ph
—S—
—S—


B-159
CH
CH
4
4
H
Ph
—CH2O—
—OCH2


B-160
CH
CH
4
4
H
Ph
singlebond
singlebond


B-161
N
CH
3
3
Me
H
—O—
—O—


B-162
N
CH
3
3
Me
H
—O—
—S—


B-163
N
CH
3
3
Me
H
—O—
—OCH2


B-164
N
CH
3
3
Me
H
—O—
singlebond


B-165
N
CH
3
3
Me
H
—S—
—O—


B-166
N
CH
3
3
Me
H
—CH2O—
—O—


B-167
N
CH
3
3
Me
H
singlebond
—O—


B-168
N
CH
3
3
Me
H
—S—
—S—


B-169
N
CH
3
3
Me
H
—CH2O—
—OCH2


B-170
N
CH
3
3
Me
H
singlebond
singlebond


B-171
N
CH
3
3
H
Me
—O—
—O—


B-172
N
CH
3
3
H
Me
—O—
—S—


B-173
N
CH
3
3
H
Me
—O—
—OCH2


B-174
N
CH
3
3
H
Me
—O—
singlebond


B-175
N
CH
3
3
H
Me
—S—
—O—


B-176
N
CH
3
3
H
Me
—CH2O—
—O—


B-177
N
CH
3
3
H
Me
singlebond
—O—


B-178
N
CH
3
3
H
Me
—S—
—S—


B-179
N
CH
3
3
H
Me
—CH2O—
—OCH2


B-180
N
CH
3
3
H
Me
singlebond
singlebond


B-181
N
CH
3
3
Ph
H
—O—
—O—


B-182
N
CH
3
3
Ph
H
—O—
—S—


B-183
N
CH
3
3
Ph
H
—O—
—OCH2


B-184
N
CH
3
3
Ph
H
—O—
singlebond


B-185
N
CH
3
3
Ph
H
—S—
—O—


B-186
N
CH
3
3
Ph
H
—CH2O—
—O—


B-187
N
CH
3
3
Ph
H
singlebond
—O—


B-188
N
CH
3
3
Ph
H
—S—
—S—


B-189
N
CH
3
3
Ph
H
—CH2O—
—OCH2


B-190
N
CH
3
3
Ph
H
singlebond
singlebond


B-191
N
CH
3
3
H
Ph
—O—
—O—


B-192
N
CH
3
3
H
Ph
—O—
—S—


B-193
N
CH
3
3
H
Ph
—O—
—OCH2


B-194
N
CH
3
3
H
Ph
—O—
singlebond


B-195
N
CH
3
3
H
Ph
—S—
—O—


B-196
N
CH
3
3
H
Ph
—CH2O—
—O—


B-197
N
CH
3
3
H
Ph
singlebond
—O—


B-198
N
CH
3
3
H
Ph
—S—
—S—


B-199
N
CH
3
3
H
Ph
—CH2O—
—OCH2


B-200
N
CH
3
3
H
Ph
singlebond
singlebond


B-201
N
CH
3
4
Me
H
—O—
—O—


B-202
N
CH
3
4
Me
H
—O—
—S—


B-203
N
CH
3
4
Me
H
—O—
—OCH2


B-204
N
CH
3
4
Me
H
—O—
singlebond


B-205
N
CH
3
4
Me
H
—S—
—O—


B-206
N
CH
3
4
Me
H
—CH2O—
—O—


B-207
N
CH
3
4
Me
H
singlebond
—O—


B-208
N
CH
3
4
Me
H
—S—
—S—


B-209
N
CH
3
4
Me
H
—CH2O—
—OCH2


B-210
N
CH
3
4
Me
H
singlebond
singlebond


B-211
N
CH
3
4
H
Me
—O—
—O—


B-212
N
CH
3
4
H
Me
—O—
—S—


B-213
N
CH
3
4
H
Me
—O—
—OCH2


B-214
N
CH
3
4
H
Me
—O—
singlebond


B-215
N
CH
3
4
H
Me
—S—
—O—


B-216
N
CH
3
4
H
Me
—CH2O—
—O—


B-217
N
CH
3
4
H
Me

—O—


B-218
N
CH
3
4
H
Me
—S—
—S—


B-219
N
CH
3
4
H
Me
—CH2O—
—OCH2


B-220
N
CH
3
4
H
Me
singlebond
singlebond
























TABLE 8





Com-










pound










No.
G1
G2
n
m
Ra
Rc
Q1
Q2







B-221
N
CH
3
4
Ph
H
—O—
—O—


B-222
N
CH
3
4
Ph
H
—O—
—S—


B-223
N
CH
3
4
Ph
H
—O—
—OCH2


B-224
N
CH
3
4
Ph
H
—O—
singlebond


B-225
N
CH
3
4
Ph
H
—S—
—O—


B-226
N
CH
3
4
Ph
H
—CH2O—
—O—


B-227
N
CH
3
4
Ph
H
singlebond
—O—


B-228
N
CH
3
4
Ph
H
—S—
—S—


B-229
N
CH
3
4
Ph
H
—CH2O—
—OCH2


B-230
N
CH
3
4
Ph
H
singlebond
singlebond


B-231
N
CH
3
4
H
Ph
—O—
—O—


B-232
N
CH
3
4
H
Ph
—O—
—S—


B-233
N
CH
3
4
H
Ph
—O—
—OCH2


B-234
N
CH
3
4
H
Ph
—O—
singlebond


B-235
N
CH
3
4
H
Ph
—S—
—O—


B-236
N
CH
3
4
H
Ph
—CH2O—
—O—


B-237
N
CH
3
4
H
Ph
singlebond
—O—


B-238
N
CH
3
4
H
Ph
—S—
—S—


B-239
N
CH
3
4
H
Ph
—CH2O—
—OCH2


B-240
N
CH
3
4
H
Ph
singlebond
singlebond


B-241
N
CH
4
3
Me
H
—O—
—O—


B-242
N
CH
4
3
Me
H
—O—
—S—


B-243
N
CH
4
3
Me
H
—O—
—OCH2


B-244
N
CH
4
3
Me
H
—O—
singlebond


B-245
N
CH
4
3
Me
H
—S—
—O—


B-246
N
CH
4
3
Me
H
—CH2O—
—O—


B-247
N
CH
4
3
Me
H
singlebond
—O—


B-248
N
CH
4
3
Me
H
—S—
—S—


B-249
N
CH
4
3
Me
H
—CH2O—
—OCH2


B-250
N
CH
4
3
Me
H
singlebond
singlebond


B-251
N
CH
4
3
H
Me
—O—
—O—


B-252
N
CH
4
3
H
Me
—O—
—S—


B-253
N
CH
4
3
H
Me
—O—
—OCH2


B-254
N
CH
4
3
H
Me
—O—
singlebond


B-255
N
CH
4
3
H
Me
—S—
—O—


B-256
N
CH
4
3
H
Me
—CH2O—
—O—


B-257
N
CH
4
3
H
Me
singlebond
—O—


B-258
N
CH
4
3
H
Me
—S—
—S—


B-259
N
CH
4
3
H
Me
—CH2O—
—OCH2


B-260
N
CH
4
3
H
Me
singlebond
singlebond


B-261
N
CH
4
3
Ph
H
—O—
—O—


B-262
N
CH
4
3
Ph
H
—O—
—S—


B-263
N
CH
4
3
Ph
H
—O—
—OCH2


B-264
N
CH
4
3
Ph
H
—O—
singlebond


B-265
N
CH
4
3
Ph
H
—S—
—O—


B-266
N
CH
4
3
Ph
H
—CH2O—
—O—


B-267
N
CH
4
3
Ph
H
singlebond
—O—


B-268
N
CH
4
3
Ph
H
—S—
—S—


B-269
N
CH
4
3
Ph
H
—CH2O—
—OCH2


B-270
N
CH
4
3
Ph
H
singlebond
singlebond


B-271
N
CH
4
3
H
Ph
—O—
—O—


B-272
N
CH
4
3
H
Ph
—O—
—S—


B-273
N
CH
4
3
H
Ph
—O—
—OCH2


B-274
N
CH
4
3
H
Ph
—O—
singlebond


B-275
N
CH
4
3
H
Ph
—S—
—O—


B-276
N
CH
4
3
H
Ph
—CH2O—
—O—


B-277
N
CH
4
3
H
Ph
singlebond
—O—


B-278
N
CH
4
3
H
Ph
—S—
—S—


B-279
N
CH
4
3
H
Ph
—CH2O—
—OCH2


B-280
N
CH
4
3
H
Ph
singlebond
singlebond


B-281
N
CH
4
4
Me
H
—O—
—O—


B-282
N
CH
4
4
Me
H
—O—
—S—


B-283
N
CH
4
4
Me
H
—O—
—OCH2


B-284
N
CH
4
4
Me
H
—O—
singlebond


B-285
N
CH
4
4
Me
H
—S—
—O—


B-286
N
CH
4
4
Me
H
—CH2O—
—O—


B-287
N
CH
4
4
Me
H
singlebond
—O—


B-288
N
CH
4
4
Me
H
—S—
—S—


B-289
N
CH
4
4
Me
H
—CH2O—
—OCH2


B-290
N
CH
4
4
Me
H
singlebond
singlebond


B-291
N
CH
4
4
H
Me
—O—
—O—


B-292
N
CH
4
4
H
Me
—O—
—S—


B-293
N
CH
4
4
H
Me
—O—
—OCH2


B-294
N
CH
4
4
H
Me
—O—
singlebond


B-295
N
CH
4
4
H
Me
—S—
—O—


B-296
N
CH
4
4
H
Me
—CH2O—
—O—


B-297
N
CH
4
4
H
Me
singlebond
—O—


B-298
N
CH
4
4
H
Me
—S—
—S—


B-299
N
CH
4
4
H
Me
—CH2O—
—OCH2


B-300
N
CH
4
4
H
Me
singlebond
singlebond


B-301
N
CH
4
4
Ph
H
—O—
—O—


B-302
N
CH
4
4
Ph
H
—O—
—S—


B-303
N
CH
4
4
Ph
H
—O—
—OCH2


B-304
N
CH
4
4
Ph
H
—O—
singlebond


B-305
N
CH
4
4
Ph
H
—S—
—O—


B-306
N
CH
4
4
Ph
H
—CH2O—
—O—


B-307
N
CH
4
4
Ph
H
singlebond
—O—


B-308
N
CH
4
4
Ph
H
—S—
—S—


B-309
N
CH
4
4
Ph
H
—CH2O—
—OCH2


B-310
N
CH
4
4
Ph
H
singlebond
singlebond


B-311
N
CH
4
4
H
Ph
—O—
—O—


B-312
N
CH
4
4
H
Ph
—O—
—S—


B-313
N
CH
4
4
H
Ph
—O—
—OCH2


B-314
N
CH
4
4
H
Ph
—O—
singlebond


B-315
N
CH
4
4
H
Ph
—S—
—O—


B-316
N
CH
4
4
H
Ph
—CH2O—
—O—


B-317
N
CH
4
4
H
Ph
singlebond
—O—


B-318
N
CH
4
4
H
Ph
—S—
—S—


B-319
N
CH
4
4
H
Ph
—CH2O—
—OCH2


B-320
N
CH
4
4
H
Ph
singlebond
singlebond


B-321
CH
N
3
3
Me
H
—O—
—O—


B-322
CH
N
3
3
Me
H
—O—
—S—


B-323
CH
N
3
3
Me
H
—O—
—OCH2


B-324
CH
N
3
3
Me
H
—O—
singlebond


B-325
CH
N
3
3
Me
H
—S—
—O—


B-326
CH
N
3
3
Me
H
—CH2O—
—O—


B-327
CH
N
3
3
Me
H
singlebond
—O—


B-328
CH
N
3
3
Me
H
—S—
—S—


B-329
CH
N
3
3
Me
H
—CH2O—
—OCH2


B-330
CH
N
3
3
Me
H
singlebond
singlebond
























TABLE 9





Com-










pound










No.
G1
G2
n
m
Ra
Rc
Q1
Q2







B-331
CH
N
3
3
H
Me
—O—
—O—


B-332
CH
N
3
3
H
Me
—O—
—S—


B-333
CH
N
3
3
H
Me
—O—
—OCH2


B-334
CH
N
3
3
H
Me
—O—
singlebond


B-335
CH
N
3
3
H
Me
—S—
—O—


B-336
CH
N
3
3
H
Me
—CH2O—
—O—


B-337
CH
N
3
3
H
Me
singlebond
—O—


B-338
CH
N
3
3
H
Me
—S—
—S—


B-339
CH
N
3
3
H
Me
—CH2O—
—OCH2


B-340
CH
N
3
3
H
Me
singlebond
singlebond


B-341
CH
N
3
3
Ph
H
—O—
—O—


B-342
CH
N
3
3
Ph
H
—O—
—S—


B-343
CH
N
3
3
Ph
H
—O—
—OCH2


B-344
CH
N
3
3
Ph
H
—O—
singlebond


B-345
CH
N
3
3
Ph
H
—S—
—O—


B-346
CH
N
3
3
Ph
H
—CH2O—
—O—


B-347
CH
N
3
3
Ph
H
singlebond
—O—


B-348
CH
N
3
3
Ph
H
—S—
—S—


B-349
CH
N
3
3
Ph
H
—CH2O—
—OCH2


B-350
CH
N
3
3
Ph
H
singlebond
singlebond


B-351
CH
N
3
3
H
Ph
—O—
—O—


B-352
CH
N
3
3
H
Ph
—O—
—S—


B-353
CH
N
3
3
H
Ph
—O—
—OCH2


B-354
CH
N
3
3
H
Ph
—O—
singlebond


B-355
CH
N
3
3
H
Ph
—S—
—O—


B-356
CH
N
3
3
H
Ph
—CH2O—
—O—


B-357
CH
N
3
3
H
Ph
singlebond
—O—


B-358
CH
N
3
3
H
Ph
—S—
—S—


B-359
CH
N
3
3
H
Ph
—CH2O—
—OCH2


B-360
CH
N
3
3
H
Ph
singlebond
singlebond


B-361
CH
N
3
4
Me
H
—O—
—O—


B-362
CH
N
3
4
Me
H
—O—
—S—


B-363
CH
N
3
4
Me
H
—O—
—OCH2


B-364
CH
N
3
4
Me
H
—O—
singlebond


B-365
CH
N
3
4
Me
H
—S—
—O—


B-366
CH
N
3
4
Me
H
—CH2O—
—O—


B-367
CH
N
3
4
Me
H
singlebond
—O—


B-368
CH
N
3
4
Me
H
—S—
—S—


B-369
CH
N
3
4
Me
H
—CH2O—
—OCH2


B-370
CH
N
3
4
Me
H
singlebond
singlebond


B-371
CH
N
3
4
H
Me
—O—
—O—


B-372
CH
N
3
4
H
Me
—O—
—S—


B-373
CH
N
3
4
H
Me
—O—
—OCH2


B-374
CH
N
3
4
H
Me
—O—
singlebond


B-375
CH
N
3
4
H
Me
—S—
—O—


B-376
CH
N
3
4
H
Me
—CH2O—
—O—


B-377
CH
N
3
4
H
Me
singlebond
—O—


B-378
CH
N
3
4
H
Me
—S—
—S—


B-379
CH
N
3
4
H
Me
—CH2O—
—OCH2


B-380
CH
N
3
4
H
Me
singlebond
singlebond


B-381
CH
N
3
4
Ph
H
—O—
—O—


B-382
CH
N
3
4
Ph
H
—O—
—S—


B-383
CH
N
3
4
Ph
H
—O—
—OCH2


B-384
CH
N
3
4
Ph
H
—O—
singlebond


B-385
CH
N
3
4
Ph
H
—S—
—O—


B-386
CH
N
3
4
Ph
H
—CH2O—
—O—


B-387
CH
N
3
4
Ph
H
singlebond
—O—


B-388
CH
N
3
4
Ph
H
—S—
—S—


B-389
CH
N
3
4
Ph
H
—CH2O—
—OCH2


B-390
CH
N
3
4
Ph
H
singlebond
singlebond


B-391
CH
N
3
4
H
Ph
—O—
—O—


B-392
CH
N
3
4
H
Ph
—O—
—S—


B-393
CH
N
3
4
H
Ph
—O—
—OCH2


B-394
CH
N
3
4
H
Ph
—O—
singlebond


B-395
CH
N
3
4
H
Ph
—S—
—O—


B-396
CH
N
3
4
H
Ph
—CH2O—
—O—


B-397
CH
N
3
4
H
Ph
singlebond
—O—


B-398
CH
N
3
4
H
Ph
—S—
—S—


B-399
CH
N
3
4
H
Ph
—CH2O—
—OCH2


B-400
CH
N
3
4
H
Ph
singlebond
singlebond


B-401
CH
N
4
3
Me
H
—O—
—O—


B-402
CH
N
4
3
Me
H
—O—
—S—


B-403
CH
N
4
3
Me
H
—O—
—OCH2


B-404
CH
N
4
3
Me
H
—O—
singlebond


B-405
CH
N
4
3
Me
H
—S—
—O—


B-406
CH
N
4
3
Me
H
—CH2O—
—O—


B-407
CH
N
4
3
Me
H
singlebond
—O—


B-408
CH
N
4
3
Me
H
—S—
—S—


B-409
CH
N
4
3
Me
H
—CH2O—
—OCH2


B-410
CH
N
4
3
Me
H
singlebond
singlebond


B-411
CH
N
4
3
H
Me
—O—
—O—


B-412
CH
N
4
3
H
Me
—O—
—S—


B-413
CH
N
4
3
H
Me
—O—
—OCH2


B-414
CH
N
4
3
H
Me
—O—
singlebond


B-415
CH
N
4
3
H
Me
—S—
—O—


B-416
CH
N
4
3
H
Me
—CH2O—
—O—


B-417
CH
N
4
3
H
Me
singlebond
—O—


B-418
CH
N
4
3
H
Me
—S—
—S—


B-419
CH
N
4
3
H
Me
—CH2O—
—OCH2


B-420
CH
N
4
3
H
Me
singlebond
singlebond


B-421
CH
N
4
3
Ph
H
—O—
—O—


B-422
CH
N
4
3
Ph
H
—O—
—S—


B-423
CH
N
4
3
Ph
H
—O—
—OCH2


B-424
CH
N
4
3
Ph
H
—O—
singlebond


B-425
CH
N
4
3
Ph
H
—S—
—O—


B-426
CH
N
4
3
Ph
H
—CH2O—
—O—


B-427
CH
N
4
3
Ph
H
singlebond
—O—


B-428
CH
N
4
3
Ph
H
—S—
—S—


B-429
CH
N
4
3
Ph
H
—CH2O—
—OCH2


B-430
CH
N
4
3
Ph
H
singlebond
singlebond


B-431
CH
N
4
3
H
Ph
—O—
—O—


B-432
CH
N
4
3
H
Ph
—O—
—S—


B-433
CH
N
4
3
H
Ph
—O—
—OCH2


B-434
CH
N
4
3
H
Ph
—O—
singlebond


B-435
CH
N
4
3
H
Ph
—S—
—O—


B-436
CH
N
4
3
H
Ph
—CH2O—
—O—


B-437
CH
N
4
3
H
Ph
singlebond
—O—


B-438
CH
N
4
3
H
Ph
—S—
—S—


B-439
CH
N
4
3
H
Ph
—CH2O—
—OCH2


B-440
CH
N
4
3
H
Ph
singlebond
singlebond
























TABLE 10





Com-










pound










No.
G1
G2
n
m
Ra
Rc
Q1
Q2







B-441
CH
N
4
4
Me
H
—O—
—O—


B-442
CH
N
4
4
Me
H
—O—
—S—


B-443
CH
N
4
4
Me
H
—O—
—OCH2


B-444
CH
N
4
4
Me
H
—O—
singlebond


B-445
CH
N
4
4
Me
H
—S—
—O—


B-446
CH
N
4
4
Me
H
—CH2O—
—O—


B-447
CH
N
4
4
Me
H
singlebond
—O—


B-448
CH
N
4
4
Me
H
—S—
—S—


B-449
CH
N
4
4
Me
H
—CH2O—
—OCH2


B-450
CH
N
4
4
Me
H
singlebond
singlebond


B-451
CH
N
4
4
H
Me
—O—
—O—


B-452
CH
N
4
4
H
Me
—O—
—S—


B-453
CH
N
4
4
H
Me
—O—
—OCH2


B-454
CH
N
4
4
H
Me
—O—
singlebond


B-455
CH
N
4
4
H
Me
—S—
—O—


B-456
CH
N
4
4
H
Me
—CH2O—
—O—


B-457
CH
N
4
4
H
Me
singlebond
—O—


B-458
CH
N
4
4
H
Me
—S—
—S—


B-459
CH
N
4
4
H
Me
—CH2O—
—OCH2


B-460
CH
N
4
4
H
Me
singlebond
singlebond


B-461
CH
N
4
4
Ph
H
—O—
—O—


B-462
CH
N
4
4
Ph
H
—O—
—S—


B-463
CH
N
4
4
Ph
H
—O—
—OCH2


B-464
CH
N
4
4
Ph
H
—O—
singlebond


B-465
CH
N
4
4
Ph
H
—S—
—O—


B-466
CH
N
4
4
Ph
H
—CH2O—
—O—


B-467
CH
N
4
4
Ph
H
singlebond
—O—


B-468
CH
N
4
4
Ph
H
—S—
—S—


B-469
CH
N
4
4
Ph
H
—CH2O—
—OCH2


B-470
CH
N
4
4
Ph
H
singlebond
singlebond


B-471
CH
N
4
4
H
Ph
—O—
—O—


B-472
CH
N
4
4
H
Ph
—O—
—S—


B-473
CH
N
4
4
H
Ph
—O—
—OCH2


B-474
CH
N
4
4
H
Ph
—O—
singlebond


B-475
CH
N
4
4
H
Ph
—S—
—O—


B-476
CH
N
4
4
H
Ph
—CH2O—
—O—


B-477
CH
N
4
4
H
Ph
singlebond
—O—


B-478
CH
N
4
4
H
Ph
—S—
—S—


B-479
CH
N
4
4
H
Ph
—CH2O—
—OCH2


B-480
CH
N
4
4
H
Ph
singlebond
singlebond


B-481
CH
CH
2
5
H
H
—O—
—O—


B-482
CH
CH
3
5
H
H
—O—
—O—


B-483
CH
CH
5
2
H
H
—O—
—O—


B-484
CH
CH
5
3
H
H
—O—
—O—











embedded image
















TABLE 11





Compound









No.
G1
G2
n
m
Ra
Q1
Q2







C-1
CH
CH
3
3
H
—O—
—O—


C-2
CH
CH
3
3
H
—O—
—S—


C-3
CH
CH
3
3
H
—O—
—OCH2


C-4
CH
CH
3
3
H
—O—
singlebond


C-5
CH
CH
3
3
H
—S—
—O—


C-6
CH
CH
3
3
H
—CH2O—
—O—


C-7
CH
CH
3
3
H
singlebond
—O—


C-8
CH
CH
3
3
H
—S—
—S—


C-9
CH
CH
3
3
H
—CH2O—
—OCH2


C-10
CH
CH
3
3
H
singlebond
singlebond


C-11
CH
CH
3
3
Me
—O—
—O—


C-12
CH
CH
3
3
Me
—O—
—S—


C-13
CH
CH
3
3
Me
—O—
—OCH2


C-14
CH
CH
3
3
Me
—O—
singlebond


C-15
CH
CH
3
3
Me
—S—
—O—


C-16
CH
CH
3
3
Me
—CH2O—
—O—


C-17
CH
CH
3
3
Me
singlebond
—O—


C-18
CH
CH
3
3
Me
—S—
—S—


C-19
CH
CH
3
3
Me
—CH2O—
—OCH2


C-20
CH
CH
3
3
Me
singlebond
singlebond


C-21
CH
CH
3
3
Ph
—O—
—O—


C-22
CH
CH
3
3
Ph
—O—
—S—


C-23
CH
CH
3
3
Ph
—O—
—OCH2


C-24
CH
CH
3
3
Ph
—O—
singlebond


C-25
CH
CH
3
3
Ph
—S—
—O—


C-26
CH
CH
3
3
Ph
—CH2O—
—O—


C-27
CH
CH
3
3
Ph
singlebond
—O—


C-28
CH
CH
3
3
Ph
—S—
—S—


C-29
CH
CH
3
3
Ph
—CH2O—
—OCH2


C-30
CH
CH
3
3
Ph
singlebond
singlebond


C-31
CH
CH
3
4
H
—O—
—O—


C-32
CH
CH
3
4
H
—O—
—S—


C-33
CH
CH
3
4
H
—O—
—OCH2


C-34
CH
CH
3
4
H
—O—
singlebond


C-35
CH
CH
3
4
H
—S—
—O—


C-36
CH
CH
3
4
H
—CH2O—
—O—


C-37
CH
CH
3
4
H
singlebond
—O—


C-38
CH
CH
3
4
H
—S—
—S—


C-39
CH
CH
3
4
H
—CH2O—
—OCH2


C-40
CH
CH
3
4
H
singlebond
singlebond


C-41
CH
CH
3
4
Me
—O—
—O—


C-42
CH
CH
3
4
Me
—O—
—S—


C-43
CH
CH
3
4
Me
—O—
—OCH2


C-44
CH
CH
3
4
Me
—O—
singlebond


C-45
CH
CH
3
4
Me
—S—
—O—


C-46
CH
CH
3
4
Me
—CH2O—
—O—


C-47
CH
CH
3
4
Me
singlebond
—O—


C-48
CH
CH
3
4
Me
—S—
—S—


C-49
CH
CH
3
4
Me
—CH2O—
—OCH2


C-50
CH
CH
3
4
Me
singlebond
singlebond


C-51
CH
CH
3
4
Ph
—O—
—O—


C-52
CH
CH
3
4
Ph
—O—
—S—


C-53
CH
CH
3
4
Ph
—O—
—OCH2


C-54
CH
CH
3
4
Ph
—O—
singlebond


C-55
CH
CH
3
4
Ph
—S—
—O—


C-56
CH
CH
3
4
Ph
—CH2O—
—O—


C-57
CH
CH
3
4
Ph
singlebond
—O—


C-58
CH
CH
3
4
Ph
—S—
—S—


C-59
CH
CH
3
4
Ph
—CH2O—
—OCH2


C-60
CH
CH
3
4
Ph
singlebond
singlebond


C-61
CH
CH
4
3
H
—O—
—O—


C-62
CH
CH
4
3
H
—O—
—S—


C-63
CH
CH
4
3
H
—O—
—OCH2


C-64
CH
CH
4
3
H
—O—
singlebond


C-65
CH
CH
4
3
H
—S—
—O—


C-66
CH
CH
4
3
H
—CH2O—
—O—


C-67
CH
CH
4
3
H
singlebond
—O—


C-68
CH
CH
4
3
H
—S—
—S—


C-69
CH
CH
4
3
H
—CH2O—
—OCH2


C-70
CH
CH
4
3
H
singlebond
singlebond


C-71
CH
CH
4
3
Me
—O—
—O—


C-72
CH
CH
4
3
Me
—O—
—S—


C-73
CH
CH
4
3
Me
—O—
—OCH2


C-74
CH
CH
4
3
Me
—O—
singlebond


C-75
CH
CH
4
3
Me
—S—
—O—


C-76
CH
CH
4
3
Me
—CH2O—
—O—


C-77
CH
CH
4
3
Me
singlebond
—O—


C-78
CH
CH
4
3
Me
—S—
—S—


C-79
CH
CH
4
3
Me
—CH2O—
—OCH2


C-80
CH
CH
4
3
Me
singlebond
singlebond


C-81
CH
CH
4
3
Ph
—O—
—O—


C-82
CH
CH
4
3
Ph
—O—
—S—


C-83
CH
CH
4
3
Ph
—O—
—OCH2


C-84
CH
CH
4
3
Ph
—O—
singlebond


C-85
CH
CH
4
3
Ph
—S—
—O—


C-86
CH
CH
4
3
Ph
—CH2O—
—O—


C-87
CH
CH
4
3
Ph
singlebond
—O—


C-88
CH
CH
4
3
Ph
—S—
—S—


C-89
CH
CH
4
3
Ph
—CH2O—
—OCH2


C-90
CH
CH
4
3
Ph
singlebond
singlebond


C-91
CH
CH
4
4
H
—O—
—O—


C-92
CH
CH
4
4
H
—O—
—S—


C-93
CH
CH
4
4
H
—O—
—OCH2


C-94
CH
CH
4
4
H
—O—
singlebond


C-95
CH
CH
4
4
H
—S—
—O—


C-96
CH
CH
4
4
H
—CH2O—
—O—


C-97
CH
CH
4
4
H
singlebond
—O—


C-98
CH
CH
4
4
H
—S—
—S—


C-99
CH
CH
4
4
H
—CH2O—
—OCH2


C-100
CH
CH
4
4
H
singlebond
singlebond


C-101
CH
CH
4
4
Me
—O—
—O—


C-102
CH
CH
4
4
Me
—O—
—S—


C-103
CH
CH
4
4
Me
—O—
—OCH2


C-104
CH
CH
4
4
Me
—O—
singlebond


C-105
CH
CH
4
4
Me
—S—
—O—


C-106
CH
CH
4
4
Me
—CH2O—
—O—


C-107
CH
CH
4
4
Me
singlebond
—O—


C-108
CH
CH
4
4
Me
—S—
—S—


C-109
CH
CH
4
4
Me
—CH2O—
—OCH2


C-110
CH
CH
4
4
Me
singlebond
singlebond























TABLE 12





Compound









No.
G1
G2
n
m
Ra
Q1
Q2







C-111
CH
CH
4
4
Ph
—O—
—O—


C-112
CH
CH
4
4
Ph
—O—
—S—


C-113
CH
CH
4
4
Ph
—O—
—OCH2


C-114
CH
CH
4
4
Ph
—O—
singlebond


C-115
CH
CH
4
4
Ph
—S—
—O—


C-116
CH
CH
4
4
Ph
—CH2O—
—O—


C-117
CH
CH
4
4
Ph
singlebond
—O—


C-118
CH
CH
4
4
Ph
—S—
—S—


C-119
CH
CH
4
4
Ph
—CH2O—
—OCH2


C-120
CH
CH
4
4
Ph
singlebond
singlebond


C-121
N
CH
3
3
H
—O—
—O—


C-122
N
CH
3
3
H
—O—
—S—


C-123
N
CH
3
3
H
—O—
—OCH2


C-124
N
CH
3
3
H
—O—
singlebond


C-125
N
CH
3
3
H
—S—
—O—


C-126
N
CH
3
3
H
—CH2O—
—O—


C-127
N
CH
3
3
H
singlebond
—O—


C-128
N
CH
3
3
H
—S—
—S—


C-129
N
CH
3
3
H
—CH2O—
—OCH2


C-130
N
CH
3
3
H
singlebond
singlebond


C-131
N
CH
3
3
Me
—O—
—O—


C-132
N
CH
3
3
Me
—O—
—S—


C-133
N
CH
3
3
Me
—O—
—OCH2


C-134
N
CH
3
3
Me
—O—
singlebond


C-135
N
CH
3
3
Me
—S—
—O—


C-136
N
CH
3
3
Me
—CH2O—
—O—


C-137
N
CH
3
3
Me
singlebond
—O—


C-138
N
CH
3
3
Me
—S—
—S—


C-139
N
CH
3
3
Me
—CH2O—
—OCH2


C-140
N
CH
3
3
Me
singlebond
singlebond


C-141
N
CH
3
3
Ph
—O—
—O—


C-142
N
CH
3
3
Ph
—O—
—S—


C-143
N
CH
3
3
Ph
—O—
—OCH2


C-144
N
CH
3
3
Ph
—O—
singlebond


C-145
N
CH
3
3
Ph
—S—
—O—


C-146
N
CH
3
3
Ph
—CH2O—
—O—


C-147
N
CH
3
3
Ph
singlebond
—O—


C-148
N
CH
3
3
Ph
—S—
—S—


C-149
N
CH
3
3
Ph
—CH2O—
—OCH2


C-150
N
CH
3
3
Ph
singlebond
singlebond


C-151
N
CH
3
4
H
—O—
—O—


C-152
N
CH
3
4
H
—O—
—S—


C-153
N
CH
3
4
H
—O—
—OCH2


C-154
N
CH
3
4
H
—O—
singlebond


C-155
N
CH
3
4
H
—S—
—O—


C-156
N
CH
3
4
H
—CH2O—
—O—


C-157
N
CH
3
4
H
singlebond
—O—


C-158
N
CH
3
4
H
—S—
—S—


C-159
N
CH
3
4
H
—CH2O—
—OCH2


C-160
N
CH
3
4
H
singlebond
singlebond


C-161
N
CH
3
4
Me
—O—
—O—


C-162
N
CH
3
4
Me
—O—
—S—


C-163
N
CH
3
4
Me
—O—
—OCH2


C-164
N
CH
3
4
Me
—O—
singlebond


C-165
N
CH
3
4
Me
—S—
—O—


C-166
N
CH
3
4
Me
—CH2O—
—O—


C-167
N
CH
3
4
Me
singlebond
—O—


C-168
N
CH
3
4
Me
—S—
—S—


C-169
N
CH
3
4
Me
—CH2O—
—OCH2


C-170
N
CH
3
4
Me
singlebond
singlebond


C-171
N
CH
3
4
Ph
—O—
—O—


C-172
N
CH
3
4
Ph
—O—
—S—


C-173
N
CH
3
4
Ph
—O—
—OCH2


C-174
N
CH
3
4
Ph
—O—
singlebond


C-175
N
CH
3
4
Ph
—S—
—O—


C-176
N
CH
3
4
Ph
—CH2O—
—O—


C-177
N
CH
3
4
Ph
singlebond
—O—


C-178
N
CH
3
4
Ph
—S—
—S—


C-179
N
CH
3
4
Ph
—CH2O—
—OCH2


C-180
N
CH
3
4
Ph
singlebond
singlebond


C-181
N
CH
4
3
H
—O—
—O—


C-182
N
CH
4
3
H
—O—
—S—


C-183
N
CH
4
3
H
—O—
—OCH2


C-184
N
CH
4
3
H
—O—
singlebond


C-185
N
CH
4
3
H
—S—
—O—


C-186
N
CH
4
3
H
—CH2O—
—O—


C-187
N
CH
4
3
H
singlebond
—O—


C-188
N
CH
4
3
H
—S—
—S—


C-189
N
CH
4
3
H
—CH2O—
—OCH2


C-190
N
CH
4
3
H
singlebond
singlebond


C-191
N
CH
4
3
Me
—O—
—O—


C-192
N
CH
4
3
Me
—O—
—S—


C-193
N
CH
4
3
Me
—O—
—OCH2


C-194
N
CH
4
3
Me
—O—
singlebond


C-195
N
CH
4
3
Me
—S—
—O—


C-196
N
CH
4
3
Me
—CH2O—
—O—


C-197
N
CH
4
3
Me
singlebond
—O—


C-198
N
CH
4
3
Me
—S—
—S—


C-199
N
CH
4
3
Me
—CH2O—
—OCH2


C-200
N
CH
4
3
Me
singlebond
singlebond


C-201
N
CH
4
3
Ph
—O—
—O—


C-202
N
CH
4
3
Ph
—O—
—S—


C-203
N
CH
4
3
Ph
—O—
—OCH2


C-204
N
CH
4
3
Ph
—O—
singlebond


C-205
N
CH
4
3
Ph
—S—
—O—


C-206
N
CH
4
3
Ph
—CH2O—
—O—


C-207
N
CH
4
3
Ph
singlebond
—O—


C-208
N
CH
4
3
Ph
—S—
—S—


C-209
N
CH
4
3
Ph
—CH2O—
—OCH2


C-210
N
CH
4
3
Ph
singlebond
singlebond


C-211
N
CH
4
4
H
—O—
—O—


C-212
N
CH
4
4
H
—O—
—S—


C-213
N
CH
4
4
H
—O—
—OCH2


C-214
N
CH
4
4
H
—O—
singlebond


C-215
N
CH
4
4
H
—S—
—O—


C-216
N
CH
4
4
H
—CH2O—
—O—


C-217
N
CH
4
4
H
singlebond
—O—


C-218
N
CH
4
4
H
—S—
—S—


C-219
N
CH
4
4
H
—CH2O—
—OCH2


C-220
N
CH
4
4
H
singlebond
singlebond























TABLE 13





Compound









No.
G1
G2
n
m
Ra
Q1
Q2







C-221
N
CH
4
4
Me
—O—
—O—


C-222
N
CH
4
4
Me
—O—
—S—


C-223
N
CH
4
4
Me
—O—
—OCH2—


C-224
N
CH
4
4
Me
—O—
singlebond


C-225
N
CH
4
4
Me
—S—
—O—


C-226
N
CH
4
4
Me
—CH2O—
—O—


C-227
N
CH
4
4
Me
singlebond
—O—


C-228
N
CH
4
4
Me
—S—
—S—


C-229
N
CH
4
4
Me
—CH2O—
—OCH2


C-230
N
CH
4
4
Me
singlebond
singlebond


C-231
N
CH
4
4
Ph
—O—
—O—


C-232
N
CH
4
4
Ph
—O—
—S—


C-233
N
CH
4
4
Ph
—O—
—OCH2


C-234
N
CH
4
4
Ph
—O—
singlebond


C-235
N
CH
4
4
Ph
—S—
—O—


C-236
N
CH
4
4
Ph
—CH2O—
—O—


C-237
N
CH
4
4
Ph
singlebond
—O—


C-238
N
CH
4
4
Ph
—S—
—S—


C-239
N
CH
4
4
Ph
—CH2O—
—OCH2


C-240
N
CH
4
4
Ph
singlebond
singlebond


C-241
CH
N
3
3
H
—O—
—O—


C-242
CH
N
3
3
H
—O—
—S—


C-243
CH
N
3
3
H
—O—
—OCH2


C-244
CH
N
3
3
H
—O—
singlebond


C-245
CH
N
3
3
H
—S—
—O—


C-246
CH
N
3
3
H
—CH2O—
—O—


C-247
CH
N
3
3
H
singlebond
—O—


C-248
CH
N
3
3
H
—S—
—S—


C-249
CH
N
3
3
H
—CH2O—
—OCH2


C-250
CH
N
3
3
H
singlebond
singlebond


C-251
CH
N
3
3
Me
—O—
—O—


C-252
CH
N
3
3
Me
—O—
—S—


C-253
CH
N
3
3
Me
—O—
—OCH2


C-254
CH
N
3
3
Me
—O—
singlebond


C-255
CH
N
3
3
Me
—S—
—O—


C-256
CH
N
3
3
Me
—CH2O—
—O—


C-257
CH
N
3
3
Me
singlebond
—O—


C-258
CH
N
3
3
Me
—S—
—S—


C-259
CH
N
3
3
Me
—CH2O—
—OCH2


C-260
CH
N
3
3
Me
singlebond
singlebond


C-261
CH
N
3
3
Ph
—O—
—O—


C-262
CH
N
3
3
Ph
—O—
—S—


C-263
CH
N
3
3
Ph
—O—
—OCH2


C-264
CH
N
3
3
Ph
—O—
singlebond


C-265
CH
N
3
3
Ph
—S—
—O—


C-266
CH
N
3
3
Ph
—CH2O—
—O—


C-267
CH
N
3
3
Ph
singlebond
—O—


C-268
CH
N
3
3
Ph
—S—
—O—


C-269
CH
N
3
3
Ph
—CH2O—
—OCH2


C-270
CH
N
3
3
Ph
singlebond
singlebond


C-271
CH
N
3
4
H
—O—
—O—


C-272
CH
N
3
4
H
—O—
—S—


C-273
CH
N
3
4
H
—O—
—OCH2


C-274
CH
N
3
4
H
—O—
singlebond


C-275
CH
N
3
4
H
—S—
—O—


C-276
CH
N
3
4
H
—CH2O—
—O—


C-277
CH
N
3
4
H
singlebond
—O—


C-278
CH
N
3
4
H
—S—
—S—


C-279
CH
N
3
4
H
—CH2O—
—OCH2


C-280
CH
N
3
4
H
singlebond
singlebond


C-281
CH
N
3
4
Me
—O—
—O—


C-282
CH
N
3
4
Me
—O—
—S—


C-283
CH
N
3
4
Me
—O—
—OCH2


C-284
CH
N
3
4
Me
—O—
singlebond


C-285
CH
N
3
4
Me
—S—
—O—


C-286
CH
N
3
4
Me
—CH2O—
—O—


C-287
CH
N
3
4
Me
singlebond
—O—


C-288
CH
N
3
4
Me
—S—
—S—


C-289
CH
N
3
4
Me
—CH2O—
—OCH2


C-290
CH
N
3
4
Me
singlebond
singlebond


C-291
CH
N
3
4
Ph
—O—
—O—


C-292
CH
N
3
4
Ph
—O—
—S—


C-293
CH
N
3
4
Ph
—O—
—OCH2


C-294
CH
N
3
4
Ph
—O—
singlebond


C-295
CH
N
3
4
Ph
—S—
—O—


C-296
CH
N
3
4
Ph
—CH2O—
—O—


C-297
CH
N
3
4
Ph
singlebond
—O—


C-298
CH
N
3
4
Ph
—S—
—S—


C-299
CH
N
3
4
Ph
—CH2O—
—OCH2


C-300
CH
N
3
4
Ph
singlebond
singlebond


C-301
CH
N
4
3
H
—O—
—O—


C-302
CH
N
4
3
H
—O—
—S—


C-303
CH
N
4
3
H
—O—
—OCH2


C-304
CH
N
4
3
H
—O—
singlebond


C-305
CH
N
4
3
H
—S—
—O—


C-306
CH
N
4
3
H
—CH2O—
—O—


C-307
CH
N
4
3
H
singlebond
—O—


C-308
CH
N
4
3
H
—S—
—S—


C-309
CH
N
4
3
H
—CH2O—
—OCH2


C-310
CH
N
4
3
H
singlebond
singlebond


C-311
CH
N
4
3
Me
—O—
—O—


C-312
CH
N
4
3
Me
—O—
—S—


C-313
CH
N
4
3
Me
—O—
—OCH2


C-314
CH
N
4
3
Me
—O—
singlebond


C-315
CH
N
4
3
Me
—S—
—O—


C-316
CH
N
4
3
Me
—CH2O—
—O—


C-317
CH
N
4
3
Me
singlebond
—O—


C-318
CH
N
4
3
Me
—S—
—S—


C-319
CH
N
4
3
Me
—CH2O—
—OCH2


C-320
CH
N
4
3
Me
singlebond
singlebond


C-321
CH
N
4
3
Ph
—O—
—O—


C-322
CH
N
4
3
Ph
—O—
—S—


C-323
CH
N
4
3
Ph
—O—
—OCH2


C-324
CH
N
4
3
Ph
—O—
singlebond


C-325
CH
N
4
3
Ph
—S—
—O—


C-326
CH
N
4
3
Ph
—CH2O—
—O—


C-327
CH
N
4
3
Ph
singlebond
—O—


C-328
CH
N
4
3
Ph
—S—
—S—


C-329
CH
N
4
3
Ph
—CH2O—
—OCH2


C-330
CH
N
4
3
Ph
singlebond
singlebond























TABLE 14





Compound









No.
G1
G2
n
m
Ra
Q1
Q2







C-331
CH
N
4
4
H
—O—
—O—


C-332
CH
N
4
4
H
—O—
—S—


C-333
CH
N
4
4
H
—O—
—OCH2


C-334
CH
N
4
4
H
—O—
singlebond


C-335
CH
N
4
4
H
—S—
—O—


C-336
CH
N
4
4
H
—CH2O—
—O—


C-337
CH
N
4
4
H
singlebond
—O—


C-338
CH
N
4
4
H
—S—
—S—


C-339
CH
N
4
4
H
—CH2O—
—OCH2


C-340
CH
N
4
4
H
singlebond
singlebond


C-341
CH
N
4
4
Me
—O—
—O—


C-342
CH
N
4
4
Me
—O—
—S—


C-343
CH
N
4
4
Me
—O—
—OCH2


C-344
CH
N
4
4
Me
—O—
singlebond


C-345
CH
N
4
4
Me
—S—
—O—


C-346
CH
N
4
4
Me
—CH2O—
—O—


C-347
CH
N
4
4
Me
singlebond
—O—


C-348
CH
N
4
4
Me
—S—
—S—


C-349
CH
N
4
4
Me
—CH2O—
—OCH2


C-350
CH
N
4
4
Me
singlebond
singlebond


C-351
CH
N
4
4
Ph
—O—
—O—


C-352
CH
N
4
4
Ph
—O—
—S—


C-353
CH
N
4
4
Ph
—O—
—OCH2


C-354
CH
N
4
4
Ph
—O—
singlebond


C-355
CH
N
4
4
Ph
—S—
—O—


C-356
CH
N
4
4
Ph
—CH2O—
—O—


C-357
CH
N
4
4
Ph
singlebond
—O—


C-358
CH
N
4
4
Ph
—S—
—S—


C-359
CH
N
4
4
Ph
—CH2O—
—OCH2


C-360
CH
N
4
4
Ph
singlebond
singlebond


C-361
CH
CH
2
5
H
—O—
—O—


C-362
CH
CH
3
5
H
—O—
—O—


C-363
CH
CH
5
2
H
—O—
—O—


C-364
CH
CH
5
2
H
—O—
—O—











embedded image
















TABLE 15





Compound









No.
G1
G2
n
m
Ra
Q1
Q2







D-1
CH
CH
3
3
H
—O—
—O—


D-2
CH
CH
3
3
H
—O—
—S—


D-3
CH
CH
3
3
H
—O—
—OCH2


D-4
CH
CH
3
3
H
—O—
singlebond


D-5
CH
CH
3
3
H
—S—
—O—


D-6
CH
CH
3
3
H
—CH2O—
—O—


D-7
CH
CH
3
3
H
singlebond
—O—


D-8
CH
CH
3
3
H
—S—
—S—


D-9
CH
CH
3
3
H
—CH2O—
—OCH2


D-10
CH
CH
3
3
H
singlebond
singlebond


D-11
CH
CH
3
3
Me
—O—
—O—


D-12
CH
CH
3
3
Me
—O—
—S—


D-13
CH
CH
3
3
Me
—O—
—OCH2


D-14
CH
CH
3
3
Me
—O—
singlebond


D-15
CH
CH
3
3
Me
—S—
—O—


D-16
CH
CH
3
3
Me
—CH2O—
—O—


D-17
CH
CH
3
3
Me
singlebond
—O—


D-18
CH
CH
3
3
Me
—S—
—S—


D-19
CH
CH
3
3
Me
—CH2O—
—OCH2


D-20
CH
CH
3
3
Me
singlebond
singlebond


D-21
CH
CH
3
3
Ph
—O—
—O—


D-22
CH
CH
3
3
Ph
—O—
—S—


D-23
CH
CH
3
3
Ph
—O—
—OCH2


D-24
CH
CH
3
3
Ph
—O—
singlebond


D-25
CH
CH
3
3
Ph
—S—
—O—


D-26
CH
CH
3
3
Ph
—CH2O—
—O—


D-27
CH
CH
3
3
Ph
singlebond
—O—


D-28
CH
CH
3
3
Ph
—S—
—S—


D-29
CH
CH
3
3
Ph
—CH2O—
—OCH2


D-30
CH
CH
3
3
Ph
singlebond
singlebond


D-31
CH
CH
3
4
H
—O—
—O—


D-32
CH
CH
3
4
H
—O—
—S—


D-33
CH
CH
3
4
H
—O—
—OCH2


D-34
CH
CH
3
4
H
—O—
singlebond


D-35
CH
CH
3
4
H
—S—
—O—


D-36
CH
CH
3
4
H
—CH2O—
—O—


D-37
CH
CH
3
4
H
singlebond
—O—


D-38
CH
CH
3
4
H
—S—
—S—


D-39
CH
CH
3
4
H
—CH2O—
—OCH2


D-40
CH
CH
3
4
H
singlebond
singlebond


D-41
CH
CH
3
4
Me
—O—
—O—


D-42
CH
CH
3
4
Me
—O—
—S—


D-43
CH
CH
3
4
Me
—O—
—OCH2


D-44
CH
CH
3
4
Me
—O—
singlebond


D-45
CH
CH
3
4
Me
—S—
—O—


D-46
CH
CH
3
4
Me
—CH2O—
—O—


D-47
CH
CH
3
4
Me
singlebond
—O—


D-48
CH
CH
3
4
Me
—S—
—S—


D-49
CH
CH
3
4
Me
—CH2O—
—OCH2


D-50
CH
CH
3
4
Me
singlebond
singlebond


D-51
CH
CH
3
4
Ph
—O—
—O—


D-52
CH
CH
3
4
Ph
—O—
—S—


D-53
CH
CH
3
4
Ph
—O—
—OCH2


D-54
CH
CH
3
4
Ph
—O—
singlebond


D-55
CH
CH
3
4
Ph
—S—
—O—


D-56
CH
CH
3
4
Ph
—CH2O—
—O—


D-57
CH
CH
3
4
Ph
singlebond
—O—


D-58
CH
CH
3
4
Ph
—S—
—S—


D-59
CH
CH
3
4
Ph
—CH2O—
—OCH2


D-60
CH
CH
3
4
Ph
singlebond
singlebond


D-61
CH
CH
4
3
H
—O—
—O—


D-62
CH
CH
4
3
H
—O—
—S—


D-63
CH
CH
4
3
H
—O—
—OCH2


D-64
CH
CH
4
3
H
—O—
singlebond


D-65
CH
CH
4
3
H
—S—
—O—


D-66
CH
CH
4
3
H
—CH2O—
—O—


D-67
CH
CH
4
3
H
singlebond
—O—


D-68
CH
CH
4
3
H
—S—
—S—


D-69
CH
CH
4
3
H
—CH2O—
—OCH2


D-70
CH
CH
4
3
H
singlebond
singlebond


D-71
CH
CH
4
3
Me
—O—
—O—


D-72
CH
CH
4
3
Me
—O—
—S—


D-73
CH
CH
4
3
Me
—O—
—OCH2


D-74
CH
CH
4
3
Me
—O—
singlebond


D-75
CH
CH
4
3
Me
—S—
—O—


D-76
CH
CH
4
3
Me
—CH2O—
—O—


D-77
CH
CH
4
3
Me
singlebond
—O—


D-78
CH
CH
4
3
Me
—S—
—S—


D-79
CH
CH
4
3
Me
—CH2O—
—OCH2


D-80
CH
CH
4
3
Me
singlebond
singlebond


D-81
CH
CH
4
3
Ph
—O—
—O—


D-82
CH
CH
4
3
Ph
—O—
—S—


D-83
CH
CH
4
3
Ph
—O—
—OCH2


D-84
CH
CH
4
3
Ph
—O—
singlebond


D-85
CH
CH
4
3
Ph
—S—
—O—


D-86
CH
CH
4
3
Ph
—CH2O—
—O—


D-87
CH
CH
4
3
Ph
singlebond
—O—


D-88
CH
CH
4
3
Ph
—S—
—S—


D-89
CH
CH
4
3
Ph
—CH2O—
—OCH2


D-90
CH
CH
4
3
Ph
singlebond
singlebond


D-91
CH
CH
4
4
H
—O—
—O—


D-92
CH
CH
4
4
H
—O—
—S—


D-93
CH
CH
4
4
H
—O—
—OCH2


D-94
CH
CH
4
4
H
—O—
singlebond


D-95
CH
CH
4
4
H
—S—
—O—


D-96
CH
CH
4
4
H
—CH2O—
—O—


D-97
CH
CH
4
4
H
singlebond
—O—


D-98
CH
CH
4
4
H
—S—
—S—


D-99
CH
CH
4
4
H
—CH2O—
—OCH2


D-100
CH
CH
4
4
H
singlebond
singlebond


D-101
CH
CH
4
4
Me
—O—
—O—


D-102
CH
CH
4
4
Me
—O—
—S—


D-103
CH
CH
4
4
Me
—O—
—OCH2


D-104
CH
CH
4
4
Me
—O—
singlebond


D-105
CH
CH
4
4
Me
—S—
—O—


D-106
CH
CH
4
4
Me
—CH2O—
—O—


D-107
CH
CH
4
4
Me
singlebond
—O—


D-108
CH
CH
4
4
Me
—S—
—S—


D-109
CH
CH
4
4
Me
—CH2O—
—OCH2


D-110
CH
CH
4
4
Me
singlebond
singlebond























TABLE 16





Compound









No.
G1
G2
n
m
Ra
Q1
Q2







D-111
CH
CH
4
4
Ph
—O—
—O—


D-112
CH
CH
4
4
Ph
—O—
—S—


D-113
CH
CH
4
4
Ph
—O—
—OCH2


D-114
CH
CH
4
4
Ph
—O—
singlebond


D-115
CH
CH
4
4
Ph
—S—
—O—


D-116
CH
CH
4
4
Ph
—CH2O—
—O—


D-117
CH
CH
4
4
Ph
singlebond
—O—


D-118
CH
CH
4
4
Ph
—S—
—S—


D-119
CH
CH
4
4
Ph
—CH2O—
—OCH2


D-120
CH
CH
4
4
Ph
singlebond
singlebond


D-121
N
CH
3
3
H
—O—
—O—


D-122
N
CH
3
3
H
—O—
—S—


D-123
N
CH
3
3
H
—O—
—OCH2


D-124
N
CH
3
3
H
—O—
singlebond


D-125
N
CH
3
3
H
—S—
—O—


D-126
N
CH
3
3
H
—CH2O—
—O—


D-127
N
CH
3
3
H
singlebond
—O—


D-128
N
CH
3
3
H
—S—
—S—


D-129
N
CH
3
3
H
—CH2O—
—OCH2


D-130
N
CH
3
3
H
singlebond
singlebond


D-131
N
CH
3
3
Me
—O—
—O—


D-132
N
CH
3
3
Me
—O—
—S—


D-133
N
CH
3
3
Me
—O—
—OCH2


D-134
N
CH
3
3
Me
—O—
singlebond


D-135
N
CH
3
3
Me
—S—
—O—


D-136
N
CH
3
3
Me
—CH2O—
—O—


D-137
N
CH
3
3
Me
singlebond
—O—


D-138
N
CH
3
3
Me
—S—
—S—


D-139
N
CH
3
3
Me
—CH2O—
—OCH2


D-140
N
CH
3
3
Me
singlebond
singlebond


D-141
N
CH
3
3
Ph
—O—
—O—


D-142
N
CH
3
3
Ph
—O—
—S—


D-143
N
CH
3
3
Ph
—O—
—OCH2


D-144
N
CH
3
3
Ph
—O—
singlebond


D-145
N
CH
3
3
Ph
—S—
—O—


D-146
N
CH
3
3
Ph
—CH2O—
—O—


D-147
N
CH
3
3
Ph
singlebond
—O—


D-148
N
CH
3
3
Ph
—S—
—S—


D-149
N
CH
3
3
Ph
—CH2O—
—OCH2


D-150
N
CH
3
3
Ph
singlebond
singlebond


D-151
N
CH
3
4
H
—O—
—O—


D-152
N
CH
3
4
H
—O—
—S—


D-153
N
CH
3
4
H
—O—
—OCH2


D-154
N
CH
3
4
H
—O—
singlebond


D-155
N
CH
3
4
H
—S—
—O—


D-156
N
CH
3
4
H
—CH2O—
—O—


D-157
N
CH
3
4
H
singlebond
—O—


D-158
N
CH
3
4
H
—S—
—S—


D-159
N
CH
3
4
H
—CH2O—
—OCH2


D-160
N
CH
3
4
H
singlebond
singlebond


D-161
N
CH
3
4
Me
—O—
—O—


D-162
N
CH
3
4
Me
—O—
—S—


D-163
N
CH
3
4
Me
—O—
—OCH2


D-164
N
CH
3
4
Me
—O—
singlebond


D-165
N
CH
3
4
Me
—S—
—O—


D-166
N
CH
3
4
Me
—CH2O—
—O—


D-167
N
CH
3
4
Me
singlebond
—O—


D-168
N
CH
3
4
Me
—S—
—S—


D-169
N
CH
3
4
Me
—CH2O—
—OCH2


D-170
N
CH
3
4
Me
singlebond
singlebond


D-171
N
CH
3
4
Ph
—O—
—O—


D-172
N
CH
3
4
Ph
—O—
—S—


D-173
N
CH
3
4
Ph
—O—
—OCH2


D-174
N
CH
3
4
Ph
—O—
singlebond


D-175
N
CH
3
4
Ph
—S—
—O—


D-176
N
CH
3
4
Ph
—CH2O—
—O—


D-177
N
CH
3
4
Ph
singlebond
—O—


D-178
N
CH
3
4
Ph
—S—
—S—


D-179
N
CH
3
4
Ph
—CH2O—
—OCH2


D-180
N
CH
3
4
Ph
singlebond
singlebond


D-181
N
CH
4
3
H
—O—
—O—


D-182
N
CH
4
3
H
—O—
—S—


D-183
N
CH
4
3
H
—O—
—OCH2


D-184
N
CH
4
3
H
—O—
singlebond


D-185
N
CH
4
3
H
—S—
—O—


D-186
N
CH
4
3
H
—CH2O—
—O—


D-187
N
CH
4
3
H
singlebond
—O—


D-188
N
CH
4
3
H
—S—
—S—


D-189
N
CH
4
3
H
—CH2O—
—OCH2


D-190
N
CH
4
3
H
singlebond
singlebond


D-191
N
CH
4
3
Me
—O—
—O—


D-192
N
CH
4
3
Me
—O—
—S—


D-193
N
CH
4
3
Me
—O—
—OCH2


D-194
N
CH
4
3
Me
—O—
singlebond


D-195
N
CH
4
3
Me
—S—
—O—


D-196
N
CH
4
3
Me
—CH2O—
—O—


D-197
N
CH
4
3
Me
singlebond
—O—


D-198
N
CH
4
3
Me
—S—
—S—


D-199
N
CH
4
3
Me
—CH2O—
—OCH2


D-200
N
CH
4
3
Me
singlebond
singlebond


D-201
N
CH
4
3
Ph
—O—
—O—


D-202
N
CH
4
3
Ph
—O—
—S—


D-203
N
CH
4
3
Ph
—O—
—OCH2


D-204
N
CH
4
3
Ph
—O—
singlebond


D-205
N
CH
4
3
Ph
—S—
—O—


D-206
N
CH
4
3
Ph
—CH2O—
—O—


D-207
N
CH
4
3
Ph
singlebond
—O—


D-208
N
CH
4
3
Ph
—S—
—S—


D-209
N
CH
4
3
Ph
—CH2O—
—OCH2


D-210
N
CH
4
3
Ph
singlebond
singlebond


D-211
N
CH
4
4
H
—O—
—O—


D-212
N
CH
4
4
H
—O—
—S—


D-213
N
CH
4
4
H
—O—
—OCH2


D-214
N
CH
4
4
H
—O—
singlebond


D-215
N
CH
4
4
H
—S—
—O—


D-216
N
CH
4
4
H
—CH2O—
—O—


D-217
N
CH
4
4
H
singlebond
—O—


D-218
N
CH
4
4
H
—S—
—S—


D-219
N
CH
4
4
H
—CH2O—
—OCH2


D-220
N
CH
4
4
H
singlebond
singlebond























TABLE 17





Compound









No.
G1
G2
n
m
Ra
Q1
Q2







D-221
N
CH
4
4
Me
—O—
—O—


D-222
N
CH
4
4
Me
—O—
—S—


D-223
N
CH
4
4
Me
—O—
—OCH2


D-224
N
CH
4
4
Me
—O—
singlebond


D-225
N
CH
4
4
Me
—S—
—O—


D-226
N
CH
4
4
Me
—CH2O—
—O—


D-227
N
CH
4
4
Me
singlebond
—O—


D-228
N
CH
4
4
Me
—S—
—S—


D-229
N
CH
4
4
Me
—CH2O—
—OCH2


D-230
N
CH
4
4
Me
singlebond
singlebond


D-231
N
CH
4
4
Ph
—O—
—O—


D-232
N
CH
4
4
Ph
—O—
—S—


D-233
N
CH
4
4
Ph
—O—
—OCH2


D-234
N
CH
4
4
Ph
—O—
singlebond


D-235
N
CH
4
4
Ph
—S—
—O—


D-236
N
CH
4
4
Ph
—CH2O—
—O—


D-237
N
CH
4
4
Ph
singlebond
—O—


D-238
N
CH
4
4
Ph
—S—
—S—


D-239
N
CH
4
4
Ph
—CH2O—
—OCH2


D-240
N
CH
4
4
Ph
singlebond
singlebond


D-241
CH
N
3
3
H
—O—
—O—


D-242
CH
N
3
3
H
—O—
—S—


D-243
CH
N
3
3
H
—O—
—OCH2


D-244
CH
N
3
3
H
—O—
singlebond


D-245
CH
N
3
3
H
—S—
—O—


D-246
CH
N
3
3
H
—CH2O—
—O—


D-247
CH
N
3
3
H
singlebond
—O—


D-248
CH
N
3
3
H
—S—
—S—


D-249
CH
N
3
3
H
—CH2O—
—OCH2


D-250
CH
N
3
3
H
singlebond
singlebond


D-251
CH
N
3
3
Me
—O—
—O—


D-252
CH
N
3
3
Me
—O—
—S—


D-253
CH
N
3
3
Me
—O—
—OCH2


D-254
CH
N
3
3
Me
—O—
singlebond


D-255
CH
N
3
3
Me
—S—
—O—


D-256
CH
N
3
3
Me
—CH2O—
—O—


D-257
CH
N
3
3
Me
singlebond
—O—


D-258
CH
N
3
3
Me
—S—
—S—


D-259
CH
N
3
3
Me
—CH2O—
—OCH2


D-260
CH
N
3
3
Me
singlebond
singlebond


D-261
CH
N
3
3
Ph
—O—
—O—


D-262
CH
N
3
3
Ph
—O—
—S—


D-263
CH
N
3
3
Ph
—O—
—OCH2


D-264
CH
N
3
3
Ph
—O—
singlebond


D-265
CH
N
3
3
Ph
—S—
—O—


D-266
CH
N
3
3
Ph
—CH2O—
—O—


D-267
CH
N
3
3
Ph
singlebond
—O—


D-268
CH
N
3
3
Ph
—S—
—S—


D-269
CH
N
3
3
Ph
—CH2O—
—OCH2


D-270
CH
N
3
3
Ph
singlebond
singlebond


D-271
CH
N
3
4
H
—O—
—O—


D-272
CH
N
3
4
H
—O—
—S—


D-273
CH
N
3
4
H
—O—
—OCH2


D-274
CH
N
3
4
H
—O—
singlebond


D-275
CH
N
3
4
H
—S—
—O—


D-276
CH
N
3
4
H
—CH2O—
—O—


D-277
CH
N
3
4
H
singlebond
—O—


D-278
CH
N
3
4
H
—S—
—S—


D-279
CH
N
3
4
H
—CH2O—
—OCH2


D-280
CH
N
3
4
H
singlebond
singlebond


D-281
CH
N
3
4
Me
—O—
—O—


D-282
CH
N
3
4
Me
—O—
—S—


D-283
CH
N
3
4
Me
—O—
—OCH2


D-284
CH
N
3
4
Me
—O—
singlebond


D-285
CH
N
3
4
Me
—S—
—O—


D-286
CH
N
3
4
Me
—CH2O—
—O—


D-287
CH
N
3
4
Me
singlebond
—O—


D-288
CH
N
3
4
Me
—S—
—S—


D-289
CH
N
3
4
Me
—CH2O—
—OCH2


D-290
CH
N
3
4
Me
singlebond
singlebond


D-291
CH
N
3
4
Ph
—O—
—O—


D-292
CH
N
3
4
Ph
—O—
—S—


D-293
CH
N
3
4
Ph
—O—
—OCH2


D-294
CH
N
3
4
Ph
—O—
singlebond


D-295
CH
N
3
4
Ph
—S—
—O—


D-296
CH
N
3
4
Ph
—CH2O—
—O—


D-297
CH
N
3
4
Ph
singlebond
—O—


D-298
CH
N
3
4
Ph
—S—
—S—


D-299
CH
N
3
4
Ph
—CH2O—
—OCH2


D-300
CH
N
3
4
Ph
singlebond
singlebond


D-301
CH
N
4
3
H
—O—
—O—


D-302
CH
N
4
3
H
—O—
—S—


D-303
CH
N
4
3
H
—O—
—OCH2


D-304
CH
N
4
3
H
—O—
singlebond


D-305
CH
N
4
3
H
—S—
—O—


D-306
CH
N
4
3
H
—CH2O—
—O—


D-307
CH
N
4
3
H
singlebond
—O—


D-308
CH
N
4
3
H
—S—
—S—


D-309
CH
N
4
3
H
—CH2O—
—OCH2


D-310
CH
N
4
3
H
singlebond
singlebond


D-311
CH
N
4
3
Me
—O—
—O—


D-312
CH
N
4
3
Me
—O—
—S—


D-313
CH
N
4
3
Me
—O—
—OCH2


D-314
CH
N
4
3
Me
—O—
singlebond


D-315
CH
N
4
3
Me
—S—
—O—


D-316
CH
N
4
3
Me
—CH2O—
—O—


D-317
CH
N
4
3
Me
singlebond
—O—


D-318
CH
N
4
3
Me
—S—
—S—


D-319
CH
N
4
3
Me
—CH2O—
—OCH2


D-320
CH
N
4
3
Me
singlebond
singlebond


D-321
CH
N
4
3
Ph
—O—
—O—


D-322
CH
N
4
3
Ph
—O—
—S—


D-323
CH
N
4
3
Ph
—O—
—OCH2


D-324
CH
N
4
3
Ph
—O—
singlebond


D-325
CH
N
4
3
Ph
—S—
—O—


D-326
CH
N
4
3
Ph
—CH2O—
—O—


D-327
CH
N
4
3
Ph
singlebond
—O—


D-328
CH
N
4
3
Ph
—S—
—S—


D-329
CH
N
4
3
Ph
—CH2O—
—OCH2


D-330
CH
N
4
3
Ph
singlebond
singlebond























TABLE 18





Compound









No.
G1
G2
n
m
Ra
Q1
Q2







D-331
CH
N
4
4
H
—O—
—O—


D-332
CH
N
4
4
H
—O—
—S—


D-333
CH
N
4
4
H
—O—
—OCH2


D-334
CH
N
4
4
H
—O—
singlebond


D-335
CH
N
4
4
H
—S—
—O—


D-336
CH
N
4
4
H
—CH2O—
—O—


D-337
CH
N
4
4
H
singlebond
—O—


D-338
CH
N
4
4
H
—S—
—S—


D-339
CH
N
4
4
H
—CH2O—
—OCH2


D-340
CH
N
4
4
H
singlebond
singlebond


D-341
CH
N
4
4
Me
—O—
—O—


D-342
CH
N
4
4
Me
—O—
—S—


D-343
CH
N
4
4
Me
—O—
—OCH2


D-344
CH
N
4
4
Me
—O—
singlebond


D-345
CH
N
4
4
Me
—S—
—O—


D-346
CH
N
4
4
Me
—CH2O—
—O—


D-347
CH
N
4
4
Me
singlebond
—O—


D-348
CH
N
4
4
Me
—S—
—S—


D-349
CH
N
4
4
Me
—CH2O—
—OCH2


D-350
CH
N
4
4
Me
singlebond
singlebond


D-351
CH
N
4
4
Ph
—O—
—O—


D-352
CH
N
4
4
Ph
—O—
—S—


D-353
CH
N
4
4
Ph
—O—
—OCH2


D-354
CH
N
4
4
Ph
—O—
singlebond


D-355
CH
N
4
4
Ph
—S—
—O—


D-356
CH
N
4
4
Ph
—CH2O—
—O—


D-357
CH
N
4
4
Ph
singlebond
—O—


D-358
CH
N
4
4
Ph
—S—
—S—


D-359
CH
N
4
4
Ph
—CH2O—
—OCH2


D-360
CH
N
4
4
Ph
singlebond
singlebond


D-361
CH
CH
2
5
H
—O—
—O—


D-362
CH
CH
3
5
H
—O—
—O—


D-363
CH
CH
5
2
H
—O—
—O—


D-364
CH
CH
5
3
H
—O—
—O—











embedded image


















TABLE 19





Com-











pound











No.
G1
G2
n
m
Ra
Rb
Rc
Q1
Q2







E-1
CH
CH
3
3
Me
H
H
—O—
—O—


E-2
CH
CH
3
3
Me
H
H
—O—
—S—


E-3
CH
CH
3
3
Me
H
H
—O—
—OCH2


E-4
CH
CH
3
3
Me
H
H
—O—
singlebond


E-5
CH
CH
3
3
Me
H
H
—S—
—O—


E-6
CH
CH
3
3
Me
H
H
—CH2O—
—O—


E-7
CH
CH
3
3
Me
H
H
singlebond
—O—


E-8
CH
CH
3
3
Me
H
H
—S—
—S—


E-9
CH
CH
3
3
Me
H
H
—CH2O—
—OCH2


E-10
CH
CH
3
3
Me
H
H
singlebond
singlebond


E-11
CH
CH
3
3
Me
Me
H
—O—
—O—


E-12
CH
CH
3
3
Me
Me
H
—O—
—S—


E-13
CH
CH
3
3
Me
Me
H
—O—
—OCH2


E-14
CH
CH
3
3
Me
Me
H
—O—
singlebond


E-15
CH
CH
3
3
Me
Me
H
—S—
—O—


E-16
CH
CH
3
3
Me
Me
H
—CH2O—
—O—


E-17
CH
CH
3
3
Me
Me
H
singlebond
—O—


E-18
CH
CH
3
3
Me
Me
H
—S—
—S—


E-19
CH
CH
3
3
Me
Me
H
—CH2O—
—OCH2


E-20
CH
CH
3
3
Me
Me
H
singlebond
singlebond


E-21
CH
CH
3
3
H
H
Me
—O—
—O—


E-22
CH
CH
3
3
H
H
Me
—O—
—S—


E-23
CH
CH
3
3
H
H
Me
—O—
—OCH2


E-24
CH
CH
3
3
H
H
Me
—O—
singlebond


E-25
CH
CH
3
3
H
H
Me
—S—
—O—


E-26
CH
CH
3
3
H
H
Me
—CH2O—
—O—


E-27
CH
CH
3
3
H
H
Me
singlebond
—O—


E-28
CH
CH
3
3
H
H
Me
—S—
—S—


E-29
CH
CH
3
3
H
H
Me
—CH2O—
—OCH2


E-30
CH
CH
3
3
H
H
Me
singlebond
singlebond


E-31
CH
CH
3
3
Ph
H
H
—O—
—O—


E-32
CH
CH
3
3
Ph
H
H
—O—
—S—


E-33
CH
CH
3
3
Ph
H
H
—O—
—OCH2


E-34
CH
CH
3
3
Ph
H
H
—O—
singlebond


E-35
CH
CH
3
3
Ph
H
H
—S—
—O—


E-36
CH
CH
3
3
Ph
H
H
—CH2O—
—O—


E-37
CH
CH
3
3
Ph
H
H
singlebond
—O—


E-38
CH
CH
3
3
Ph
H
H
—S—
—S—


E-39
CH
CH
3
3
Ph
H
H
—CH2O—
—OCH2


E-40
CH
CH
3
3
Ph
H
H
singlebond
singlebond


E-41
CH
CH
3
4
Me
H
H
—O—
—O—


E-42
CH
CH
3
4
Me
H
H
—O—
—S—


E-43
CH
CH
3
4
Me
H
H
—O—
—OCH2


E-44
CH
CH
3
4
Me
H
H
—O—
singlebond


E-45
CH
CH
3
4
Me
H
H
—S—
—O—


E-46
CH
CH
3
4
Me
H
H
—CH2O—
—O—


E-47
CH
CH
3
4
Me
H
H
singlebond
—O—


E-48
CH
CH
3
4
Me
H
H
—S—
—S—


E-49
CH
CH
3
4
Me
H
H
—CH2O—
—OCH2


E-50
CH
CH
3
4
Me
H
H
singlebond
singlebond


E-51
CH
CH
3
4
Me
Me
H
—O—
—O—


E-52
CH
CH
3
4
Me
Me
H
—O—
—S—


E-53
CH
CH
3
4
Me
Me
H
—O—
—OCH2


E-54
CH
CH
3
4
Me
Me
H
—O—
singlebond


E-55
CH
CH
3
4
Me
Me
H
—S—
—O—


E-56
CH
CH
3
4
Me
Me
H
—CH2O—
—O—


E-57
CH
CH
3
4
Me
Me
H
singlebond
—O—


E-58
CH
CH
3
4
Me
Me
H
—S—
—S—


E-59
CH
CH
3
4
Me
Me
H
—CH2O—
—OCH2


E-60
CH
CH
3
4
Me
Me
H
singlebond
singlebond


E-61
CH
CH
3
4
H
H
Me
—O—
—O—


E-62
CH
CH
3
4
H
H
Me
—O—
—S—


E-63
CH
CH
3
4
H
H
Me
—O—
—OCH2


E-64
CH
CH
3
4
H
H
Me
—O—
singlebond


E-65
CH
CH
3
4
H
H
Me
—S—
—O—


E-66
CH
CH
3
4
H
H
Me
—CH2O—
—O—


E-67
CH
CH
3
4
H
H
Me
singlebond
—O—


E-68
CH
CH
3
4
H
H
Me
—S—
—S—


E-69
CH
CH
3
4
H
H
Me
—CH2O—
—OCH2


E-70
CH
CH
3
4
H
H
Me
singlebond
singlebond


E-71
CH
CH
3
4
Ph
H
H
—O—
—O—


E-72
CH
CH
3
4
Ph
H
H
—O—
—S—


E-73
CH
CH
3
4
Ph
H
H
—O—
—OCH2


E-74
CH
CH
3
4
Ph
H
H
—O—
singlebond


E-75
CH
CH
3
4
Ph
H
H
—S—
—O—


E-76
CH
CH
3
4
Ph
H
H
—CH2O—
—O—


E-77
CH
CH
3
4
Ph
H
H
singlebond
—O—


E-78
CH
CH
3
4
Ph
H
H
—S—
—S—


E-79
CH
CH
3
4
Ph
H
H
—CH2O—
—OCH2


E-80
CH
CH
3
4
Ph
H
H
singlebond
singlebond


E-81
CH
CH
4
3
Me
H
H
—O—
—O—


E-82
CH
CH
4
3
Me
H
H
—O—
—S—


E-83
CH
CH
4
3
Me
H
H
—O—
—OCH2


E-84
CH
CH
4
3
Me
H
H
—O—
singlebond


E-85
CH
CH
4
3
Me
H
H
—S—
—O—


E-86
CH
CH
4
3
Me
H
H
—CH2O—
—O—


E-87
CH
CH
4
3
Me
H
H
singlebond
—O—


E-88
CH
CH
4
3
Me
H
H
—S—
—S—


E-89
CH
CH
4
3
Me
H
H
—CH2O—
—OCH2


E-90
CH
CH
4
3
Me
H
H
singlebond
singlebond


E-91
CH
CH
4
3
Me
Me
H
—O—
—O—


E-92
CH
CH
4
3
Me
Me
H
—O—
—S—


E-93
CH
CH
4
3
Me
Me
H
—O—
—OCH2


E-94
CH
CH
4
3
Me
Me
H
—O—
singlebond


E-95
CH
CH
4
3
Me
Me
H
—S—
—O—


E-96
CH
CH
4
3
Me
Me
H
—CH2O—
—O—


E-97
CH
CH
4
3
Me
Me
H
singlebond
—O—


E-98
CH
CH
4
3
Me
Me
H
—S—
—S—


E-99
CH
CH
4
3
Me
Me
H
—CH2O—
—OCH2


E-100
CH
CH
4
3
Me
Me
H
singlebond
singlebond


E-101
CH
CH
4
3
H
H
Me
—O—
—O—


E-102
CH
CH
4
3
H
H
Me
—O—
—S—


E-103
CH
CH
4
3
H
H
Me
—O—
—OCH2


E-104
CH
CH
4
3
H
H
Me
—O—
singlebond


E-105
CH
CH
4
3
H
H
Me
—S—
—O—


E-106
CH
CH
4
3
H
H
Me
—CH2O—
—O—


E-107
CH
CH
4
3
H
H
Me
singlebond
—O—


E-108
CH
CH
4
3
H
H
Me
—S—
—S—


E-109
CH
CH
4
3
H
H
Me
—CH2O—
—OCH2


E-110
CH
CH
4
3
H
H
Me
singlebond
singlebond

























TABLE 20





Com-











pound











No.
G1
G2
n
m
Ra
Rb
Rc
Q1
Q2







E-111
CH
CH
4
3
Ph
H
H
—O—
—O—


E-112
CH
CH
4
3
Ph
H
H
—O—
—S—


E-113
CH
CH
4
3
Ph
H
H
—O—
—OCH2


E-114
CH
CH
4
3
Ph
H
H
—O—
singlebond


E-115
CH
CH
4
3
Ph
H
H
—S—
—O—


E-116
CH
CH
4
3
Ph
H
H
—CH2O—
—O—


E-117
CH
CH
4
3
Ph
H
H
singlebond
—O—


E-118
CH
CH
4
3
Ph
H
H
—S—
—S—


E-119
CH
CH
4
3
Ph
H
H
—CH2O—
—OCH2


E-120
CH
CH
4
3
Ph
H
H
singlebond
singlebond


E-121
CH
CH
4
4
Me
H
H
—O—
—O—


E-122
CH
CH
4
4
Me
H
H
—O—
—S—


E-123
CH
CH
4
4
Me
H
H
—O—
—OCH2


E-124
CH
CH
4
4
Me
H
H
—O—
singlebond


E-125
CH
CH
4
4
Me
H
H
—S—
—O—


E-126
CH
CH
4
4
Me
H
H
—CH2O—
—O—


E-127
CH
CH
4
4
Me
H
H
singlebond
—O—


E-128
CH
CH
4
4
Me
H
H
—S—
—S—


E-129
CH
CH
4
4
Me
H
H
—CH2O—
—OCH2


E-130
CH
CH
4
4
Me
H
H
singlebond
singlebond


E-131
CH
CH
4
4
Me
Me
H
—O—
—O—


E-132
CH
CH
4
4
Me
Me
H
—O—
—S—


E-133
CH
CH
4
4
Me
Me
H
—O—
—OCH2


E-134
CH
CH
4
4
Me
Me
H
—O—
singlebond


E-135
CH
CH
4
4
Me
Me
H
—S—
—O—


E-136
CH
CH
4
4
Me
Me
H
—CH2O—
—O—


E-137
CH
CH
4
4
Me
Me
H
singlebond
—O—


E-138
CH
CH
4
4
Me
Me
H
—S—
—S—


E-139
CH
CH
4
4
Me
Me
H
—CH2O—
—OCH2


E-140
CH
CH
4
4
Me
Me
H
singlebond
singlebond


E-141
CH
CH
4
4
H
H
Me
—O—
—O—


E-142
CH
CH
4
4
H
H
Me
—O—
—S—


E-143
CH
CH
4
4
H
H
Me
—O—
—OCH2


E-144
CH
CH
4
4
H
H
Me
—O—
singlebond


E-145
CH
CH
4
4
H
H
Me
—S—
—O—


E-146
CH
CH
4
4
H
H
Me
—CH2O—
—O—


E-147
CH
CH
4
4
H
H
Me
singlebond
—O—


E-148
CH
CH
4
4
H
H
Me
—S—
—S—


E-149
CH
CH
4
4
H
H
Me
—CH2O—
—OCH2


E-150
CH
CH
4
4
H
H
Me
singlebond
singlebond


E-151
CH
CH
4
4
Ph
H
H
—O—
—O—


E-152
CH
CH
4
4
Ph
H
H
—O—
—S—


E-153
CH
CH
4
4
Ph
H
H
—O—
—OCH2


E-154
CH
CH
4
4
Ph
H
H
—O—
singlebond


E-155
CH
CH
4
4
Ph
H
H
—S—
—O—


E-156
CH
CH
4
4
Ph
H
H
—CH2O—
—O—


E-157
CH
CH
4
4
Ph
H
H
singlebond
—O—


E-158
CH
CH
4
4
Ph
H
H
—S—
—S—


E-159
CH
CH
4
4
Ph
H
H
—CH2O—
—OCH2


E-160
CH
CH
4
4
Ph
H
H
singlebond
singlebond


E-161
N
CH
3
3
Me
H
H
—O—
—O—


E-162
N
CH
3
3
Me
H
H
—O—
—S—


E-163
N
CH
3
3
Me
H
H
—O—
—OCH2


E-164
N
CH
3
3
Me
H
H
—O—
singlebond


E-165
N
CH
3
3
Me
H
H
—S—
—O—


E-166
N
CH
3
3
Me
H
H
—CH2O—
—O—


E-167
N
CH
3
3
Me
H
H
singlebond
—O—


E-168
N
CH
3
3
Me
H
H
—S—
—S—


E-169
N
CH
3
3
Me
H
H
—CH2O—
—OCH2


E-170
N
CH
3
3
Me
H
H
singlebond
singlebond


E-171
N
CH
3
3
Me
Me
H
—O—
—O—


E-172
N
CH
3
3
Me
Me
H
—O—
—S—


E-173
N
CH
3
3
Me
Me
H
—O—
—OCH2


E-174
N
CH
3
3
Me
Me
H
—O—
singlebond


E-175
N
CH
3
3
Me
Me
H
—S—
—O—


E-176
N
CH
3
3
Me
Me
H
—CH2O—
—O—


E-177
N
CH
3
3
Me
Me
H
singlebond
—O—


E-178
N
CH
3
3
Me
Me
H
—S—
—S—


E-179
N
CH
3
3
Me
Me
H
—CH2O—
—OCH2


E-180
N
CH
3
3
Me
Me
H
singlebond
singlebond


E-181
N
CH
3
3
H
H
Me
—O—
—O—


E-182
N
CH
3
3
H
H
Me
—O—
—S—


E-183
N
CH
3
3
H
H
Me
—O—
—OCH2


E-184
N
CH
3
3
H
H
Me
—O—
singlebond


E-185
N
CH
3
3
H
H
Me
—S—
—O—


E-186
N
CH
3
3
H
H
Me
—CH2O—
—O—


E-187
N
CH
3
3
H
H
Me
singlebond
—O—


E-188
N
CH
3
3
H
H
Me
—S—
—S—


E-189
N
CH
3
3
H
H
Me
—CH2O—
—OCH2


E-190
N
CH
3
3
H
H
Me
singlebond
singlebond


E-191
N
CH
3
3
Ph
H
H
—O—
—O—


E-192
N
CH
3
3
Ph
H
H
—O—
—S—


E-193
N
CH
3
3
Ph
H
H
—O—
—OCH2


E-194
N
CH
3
3
Ph
H
H
—O—
singlebond


E-195
N
CH
3
3
Ph
H
H
—S—
—O—


E-196
N
CH
3
3
Ph
H
H
—CH2O—
—O—


E-197
N
CH
3
3
Ph
H
H
singlebond
—O—


E-198
N
CH
3
3
Ph
H
H
—S—
—S—


E-199
N
CH
3
3
Ph
H
H
—CH2O—
—OCH2


E-200
N
CH
3
3
Ph
H
H
singlebond
singlebond


E-201
N
CH
3
4
Me
H
H
—O—
—O—


E-202
N
CH
3
4
Me
H
H
—O—
—S—


E-203
N
CH
3
4
Me
H
H
—O—
—OCH2


E-204
N
CH
3
4
Me
H
H
—O—
singlebond


E-205
N
CH
3
4
Me
H
H
—S—
—O—


E-206
N
CH
3
4
Me
H
H
—CH2O—
—O—


E-207
N
CH
3
4
Me
H
H
singlebond
—O—


E-208
N
CH
3
4
Me
H
H
—S—
—S—


E-209
N
CH
3
4
Me
H
H
—CH2O—
—OCH2


E-210
N
CH
3
4
Me
H
H
singlebond
singlebond


E-211
N
CH
3
4
Me
Me
H
—O—
—O—


E-212
N
CH
3
4
Me
Me
H
—O—
—S—


E-213
N
CH
3
4
Me
Me
H
—O—
—OCH2


E-214
N
CH
3
4
Me
Me
H
—O—
singlebond


E-215
N
CH
3
4
Me
Me
H
—S—
—O—


E-216
N
CH
3
4
Me
Me
H
—CH2O—
—O—


E-217
N
CH
3
4
Me
Me
H
singlebond
—O—


E-218
N
CH
3
4
Me
Me
H
—S—
—S—


E-219
N
CH
3
4
Me
Me
H
—CH2O—
—OCH2


E-220
N
CH
3
4
Me
Me
H
singlebond
singlebond

























TABLE 21





Com-











pound











No.
G1
G2
n
m
Ra
Rb
Rc
Q1
Q2







E-221
N
CH
3
4
H
H
Me
—O—
—O—


E-222
N
CH
3
4
H
H
Me
—O—
—S—


E-223
N
CH
3
4
H
H
Me
—O—
—OCH2


E-224
N
CH
3
4
H
H
Me
—O—
singlebond


E-225
N
CH
3
4
H
H
Me
—S—
—O—


E-226
N
CH
3
4
H
H
Me
—CH2O—
—O—


E-227
N
CH
3
4
H
H
Me
singlebond
—O—


E-228
N
CH
3
4
H
H
Me
—S—
—S—


E-229
N
CH
3
4
H
H
Me
—CH2O—
—OCH2


E-230
N
CH
3
4
H
H
Me
singlebond
singlebond


E-231
N
CH
3
4
Ph
H
H
—O—
—O—


E-232
N
CH
3
4
Ph
H
H
—O—
—S—


E-233
N
CH
3
4
Ph
H
H
—O—
—OCH2


E-234
N
CH
3
4
Ph
H
H
—O—
singlebond


E-235
N
CH
3
4
Ph
H
H
—S—
—O—


E-236
N
CH
3
4
Ph
H
H
—CH2O—
—O—


E-237
N
CH
3
4
Ph
H
H
singlebond
—O—


E-238
N
CH
3
4
Ph
H
H
—S—
—S—


E-239
N
CH
3
4
Ph
H
H
—CH2O—
—OCH2


E-240
N
CH
3
4
Ph
H
H
singlebond
singlebond


E-241
N
CH
4
3
Me
H
H
—O—
—O—


E-242
N
CH
4
3
Me
H
H
—O—
—S—


E-243
N
CH
4
3
Me
H
H
—O—
—OCH2


E-244
N
CH
4
3
Me
H
H
—O—
singlebond


E-245
N
CH
4
3
Me
H
H
—S—
—O—


E-246
N
CH
4
3
Me
H
H
—CH2O—
—O—


E-247
N
CH
4
3
Me
H
H
singlebond
—O—


E-248
N
CH
4
3
Me
H
H
—S—
—S—


E-249
N
CH
4
3
Me
H
H
—CH2O—
—OCH2


E-250
N
CH
4
3
Me
H
H
singlebond
singlebond


E-251
N
CH
4
3
Me
Me
H
—O—
—O—


E-252
N
CH
4
3
Me
Me
H
—O—
—S—


E-253
N
CH
4
3
Me
Me
H
—O—
—OCH2


E-254
N
CH
4
3
Me
Me
H
—O—
singlebond


E-255
N
CH
4
3
Me
Me
H
—S—
—O—


E-256
N
CH
4
3
Me
Me
H
—CH2O—
—O—


E-257
N
CH
4
3
Me
Me
H
singlebond
—O—


E-258
N
CH
4
3
Me
Me
H
—S—
—S—


E-259
N
CH
4
3
Me
Me
H
—CH2O—
—OCH2


E-260
N
CH
4
3
Me
Me
H
singlebond
singlebond


E-261
N
CH
4
3
H
H
Me
—O—
—O—


E-262
N
CH
4
3
H
H
Me
—O—
—S—


E-263
N
CH
4
3
H
H
Me
—O—
—OCH2


E-264
N
CH
4
3
H
H
Me
—O—
singlebond


E-265
N
CH
4
3
H
H
Me
—S—
—O—


E-266
N
CH
4
3
H
H
Me
—CH2O—
—O—


E-267
N
CH
4
3
H
H
Me
singlebond
—O—


E-268
N
CH
4
3
H
H
Me
—S—
—S—


E-269
N
CH
4
3
H
H
Me
—CH2O—
—OCH2


E-270
N
CH
4
3
H
H
Me
singlebond
singlebond


E-271
N
CH
4
3
Ph
H
H
—O—
—O—


E-272
N
CH
4
3
Ph
H
H
—O—
—S—


E-273
N
CH
4
3
Ph
H
H
—O—
—OCH2


E-274
N
CH
4
3
Ph
H
H
—O—
singlebond


E-275
N
CH
4
3
Ph
H
H
—S—
—O—


E-276
N
CH
4
3
Ph
H
H
—CH2O—
—O—


E-277
N
CH
4
3
Ph
H
H
singlebond
—O—


E-278
N
CH
4
3
Ph
H
H
—S—
—S—


E-279
N
CH
4
3
Ph
H
H
—CH2O—
—OCH2


E-280
N
CH
4
3
Ph
H
H
singlebond
singlebond


E-281
N
CH
4
4
Me
H
H
—O—
—O—


E-282
N
CH
4
4
Me
H
H
—O—
—S—


E-283
N
CH
4
4
Me
H
H
—O—
—OCH2


E-284
N
CH
4
4
Me
H
H
—O—
singlebond


E-285
N
CH
4
4
Me
H
H
—S—
—O—


E-286
N
CH
4
4
Me
H
H
—CH2O—
—O—


E-287
N
CH
4
4
Me
H
H
singlebond
—O—


E-288
N
CH
4
4
Me
H
H
—S—
—S—


E-289
N
CH
4
4
Me
H
H
—CH2O—
—OCH2


E-290
N
CH
4
4
Me
H
H
singlebond
singlebond


E-291
N
CH
4
4
Me
Me
H
—O—
—O—


E-292
N
CH
4
4
Me
Me
H
—O—
—S—


E-293
N
CH
4
4
Me
Me
H
—O—
—OCH2


E-294
N
CH
4
4
Me
Me
H
—O—
singlebond


E-295
N
CH
4
4
Me
Me
H
—S—
—O—


E-296
N
CH
4
4
Me
Me
H
—CH2O—
—O—


E-297
N
CH
4
4
Me
Me
H
singlebond
—O—


E-298
N
CH
4
4
Me
Me
H
—S—
—S—


E-299
N
CH
4
4
Me
Me
H
—CH2O—
—OCH2


E-300
N
CH
4
4
Me
Me
H
singlebond
singlebond


E-301
N
CH
4
4
H
H
Me
—O—
—O—


E-302
N
CH
4
4
H
H
Me
—O—
—S—


E-303
N
CH
4
4
H
H
Me
—O—
—OCH2


E-304
N
CH
4
4
H
H
Me
—O—
singlebond


E-305
N
CH
4
4
H
H
Me
—S—
—O—


E-306
N
CH
4
4
H
H
Me
—CH2O—
—O—


E-307
N
CH
4
4
H
H
Me
singlebond
—O—


E-308
N
CH
4
4
H
H
Me
—S—
—S—


E-309
N
CH
4
4
H
H
Me
—CH2O—
—OCH2


E-310
N
CH
4
4
H
H
Me
singlebond
singlebond


E-311
N
CH
4
4
Ph
H
H
—O—
—O—


E-312
N
CH
4
4
Ph
H
H
—O—
—S—


E-313
N
CH
4
4
Ph
H
H
—O—
—OCH2


E-314
N
CH
4
4
Ph
H
H
—O—
singlebond


E-315
N
CH
4
4
Ph
H
H
—S—
—O—


E-316
N
CH
4
4
Ph
H
H
—CH2O—
—O—


E-317
N
CH
4
4
Ph
H
H
singlebond
—O—


E-318
N
CH
4
4
Ph
H
H
—S—
—S—


E-319
N
CH
4
4
Ph
H
H
—CH2O—
—OCH2


E-320
N
CH
4
4
Ph
H
H
singlebond
singlebond


E-321
CH
N
3
3
Me
H
H
—O—
—O—


E-322
CH
N
3
3
Me
H
H
—O—
—S—


E-323
CH
N
3
3
Me
H
H
—O—
—OCH2


E-324
CH
N
3
3
Me
H
H
—O—
singlebond


E-325
CH
N
3
3
Me
H
H
—S—
—O—


E-326
CH
N
3
3
Me
H
H
—CH2O—
—O—


E-327
CH
N
3
3
Me
H
H
singlebond
—O—


E-328
CH
N
3
3
Me
H
H
—S—
—S—


E-329
CH
N
3
3
Me
H
H
—CH2O—
—OCH2


E-330
CH
N
3
3
Me
H
H
singlebond
singlebond

























TABLE 22





Com-











pound











No.
G1
G2
n
m
Ra
Rb
Rc
Q1
Q2







E-331
CH
N
3
3
Me
Me
H
—O—
—O—


E-332
CH
N
3
3
Me
Me
H
—O—
—S—


E-333
CH
N
3
3
Me
Me
H
—O—
—OCH2


E-334
CH
N
3
3
Me
Me
H
—O—
singlebond


E-335
CH
N
3
3
Me
Me
H
—S—
—O—


E-336
CH
N
3
3
Me
Me
H
—CH2O—
—O—


E-337
CH
N
3
3
Me
Me
H
singlebond
—O—


E-338
CH
N
3
3
Me
Me
H
—S—
—S—


E-339
CH
N
3
3
Me
Me
H
—CH2O—
—OCH2


E-340
CH
N
3
3
Me
Me
H
singlebond
singlebond


E-341
CH
N
3
3
H
H
Me
—O—
—O—


E-342
CH
N
3
3
H
H
Me
—O—
—S—


E-343
CH
N
3
3
H
H
Me
—O—
—OCH2


E-344
CH
N
3
3
H
H
Me
—O—
singlebond


E-345
CH
N
3
3
H
H
Me
—S—
—O—


E-346
CH
N
3
3
H
H
Me
—CH2O—
—O—


E-347
CH
N
3
3
H
H
Me
singlebond
—O—


E-348
CH
N
3
3
H
H
Me
—S—
—S—


E-349
CH
N
3
3
H
H
Me
—CH2O—
—OCH2


E-350
CH
N
3
3
H
H
Me
singlebond
singlebond


E-351
CH
N
3
3
Ph
H
H
—O—
—O—


E-352
CH
N
3
3
Ph
H
H
—O—
—S—


E-353
CH
N
3
3
Ph
H
H
—O—
—OCH2


E-354
CH
N
3
3
Ph
H
H
—O—
singlebond


E-355
CH
N
3
3
Ph
H
H
—S—
—O—


E-356
CH
N
3
3
Ph
H
H
—CH2O—
—O—


E-357
CH
N
3
3
Ph
H
H
singlebond
—O—


E-358
CH
N
3
3
Ph
H
H
—S—
—S—


E-359
CH
N
3
3
Ph
H
H
—CH2O—
—OCH2


E-360
CH
N
3
3
Ph
H
H
singlebond
singlebond


E-361
CH
N
3
4
Me
H
H
—O—
—O—


E-362
CH
N
3
4
Me
H
H
—O—
—S—


E-363
CH
N
3
4
Me
H
H
—O—
—OCH2


E-364
CH
N
3
4
Me
H
H
—O—
singlebond


E-365
CH
N
3
4
Me
H
H
—S—
—O—


E-366
CH
N
3
4
Me
H
H
—CH2O—
—O—


E-367
CH
N
3
4
Me
H
H
singlebond
—O—


E-368
CH
N
3
4
Me
H
H
—S—
—S—


E-369
CH
N
3
4
Me
H
H
—CH2O—
—OCH2


E-370
CH
N
3
4
Me
H
H
singlebond
singlebond


E-371
CH
N
3
4
Me
Me
H
—O—
—O—


E-372
CH
N
3
4
Me
Me
H
—O—
—S—


E-373
CH
N
3
4
Me
Me
H
—O—
—OCH2


E-374
CH
N
3
4
Me
Me
H
—O—
singlebond


E-375
CH
N
3
4
Me
Me
H
—S—
—O—


E-376
CH
N
3
4
Me
Me
H
—CH2O—
—O—


E-377
CH
N
3
4
Me
Me
H
singlebond
—O—


E-378
CH
N
3
4
Me
Me
H
—S—
—S—


E-379
CH
N
3
4
Me
Me
H
—CH2O—
—OCH2


E-380
CH
N
3
4
Me
Me
H
singlebond
singlebond


E-381
CH
N
3
4
H
H
Me
—O—
—O—


E-382
CH
N
3
4
H
H
Me
—O—
—S—


E-383
CH
N
3
4
H
H
Me
—O—
—OCH2


E-384
CH
N
3
4
H
H
Me
—O—
singlebond


E-385
CH
N
3
4
H
H
Me
—S—
—O—


E-386
CH
N
3
4
H
H
Me
—CH2O—
—O—


E-387
CH
N
3
4
H
H
Me
singlebond
—O—


E-388
CH
N
3
4
H
H
Me
—S—
—S—


E-389
CH
N
3
4
H
H
Me
—CH2O—
—OCH2


E-390
CH
N
3
4
H
H
Me
singlebond
singlebond


E-391
CH
N
3
4
Ph
H
H
—O—
—O—


E-392
CH
N
3
4
Ph
H
H
—O—
—S—


E-393
CH
N
3
4
Ph
H
H
—O—
—OCH2


E-394
CH
N
3
4
Ph
H
H
—O—
singlebond


E-395
CH
N
3
4
Ph
H
H
—S—
—O—


E-396
CH
N
3
4
Ph
H
H
—CH2O—
—O—


E-397
CH
N
3
4
Ph
H
H
singlebond
—O—


E-398
CH
N
3
4
Ph
H
H
—S—
—S—


E-399
CH
N
3
4
Ph
H
H
—CH2O—
—OCH2


E-400
CH
N
3
4
Ph
H
H
singlebond
singlebond


E-401
CH
N
4
3
Me
H
H
—O—
—O—


E-402
CH
N
4
3
Me
H
H
—O—
—S—


E-403
CH
N
4
3
Me
H
H
—O—
—OCH2


E-404
CH
N
4
3
Me
H
H
—O—
singlebond


E-405
CH
N
4
3
Me
H
H
—S—
—O—


E-406
CH
N
4
3
Me
H
H
—CH2O—
—O—


E-407
CH
N
4
3
Me
H
H
singlebond
—O—


E-408
CH
N
4
3
Me
H
H
—S—
—S—


E-409
CH
N
4
3
Me
H
H
—CH2O—
—OCH2


E-410
CH
N
4
3
Me
H
H
singlebond
singlebond


E-411
CH
N
4
3
Me
Me
H
—O—
—O—


E-412
CH
N
4
3
Me
Me
H
—O—
—S—


E-413
CH
N
4
3
Me
Me
H
—O—
—OCH2


E-414
CH
N
4
3
Me
Me
H
—O—
singlebond


E-415
CH
N
4
3
Me
Me
H
—S—
—O—


E-416
CH
N
4
3
Me
Me
H
—CH2O—
—O—


E-417
CH
N
4
3
Me
Me
H
singlebond
—O—


E-418
CH
N
4
3
Me
Me
H
—S—
—S—


E-419
CH
N
4
3
Me
Me
H
—CH2O—
—OCH2


E-420
CH
N
4
3
Me
Me
H
singlebond
singlebond


E-421
CH
N
4
3
H
H
Me
—O—
—O—


E-422
CH
N
4
3
H
H
Me
—O—
—S—


E-423
CH
N
4
3
H
H
Me
—O—
—OCH2


E-424
CH
N
4
3
H
H
Me
—O—
singlebond


E-425
CH
N
4
3
H
H
Me
—S—
—O—


E-426
CH
N
4
3
H
H
Me
—CH2O—
—O—


E-427
CH
N
4
3
H
H
Me
singlebond
—O—


E-428
CH
N
4
3
H
H
Me
—S—
—S—


E-429
CH
N
4
3
H
H
Me
—CH2O—
—OCH2


E-430
CH
N
4
3
H
H
Me
singlebond
singlebond


E-431
CH
N
4
3
Ph
H
H
—O—
—O—


E-432
CH
N
4
3
Ph
H
H
—O—
—S—


E-433
CH
N
4
3
Ph
H
H
—O—
—OCH2


E-434
CH
N
4
3
Ph
H
H
—O—
singlebond


E-435
CH
N
4
3
Ph
H
H
—S—
—O—


E-436
CH
N
4
3
Ph
H
H
—CH2O—
—O—


E-437
CH
N
4
3
Ph
H
H
singlebond
—O—


E-438
CH
N
4
3
Ph
H
H
—S—
—S—


E-439
CH
N
4
3
Ph
H
H
—CH2O—
—OCH2


E-440
CH
N
4
3
Ph
H
H
singlebond
singlebond

























TABLE 23





Com-











pound











No.
G1
G2
n
m
Ra
Rb
Rc
Q1
Q2







E-441
CH
N
4
4
Me
H
H
—O—
—O—


E-442
CH
N
4
4
Me
H
H
—O—
—S—


E-443
CH
N
4
4
Me
H
H
—O—
—OCH2


E-444
CH
N
4
4
Me
H
H
—O—
singlebond


E-445
CH
N
4
4
Me
H
H
—S—
—O—


E-446
CH
N
4
4
Me
H
H
—CH2O—
—O—


E-447
CH
N
4
4
Me
H
H
singlebond
—O—


E-448
CH
N
4
4
Me
H
H
—S—
—S—


E-449
CH
N
4
4
Me
H
H
—CH2O—
—OCH2


E-450
CH
N
4
4
Me
H
H
singlebond
singlebond


E-451
CH
N
4
4
Me
Me
H
—O—
—O—


E-452
CH
N
4
4
Me
Me
H
—O—
—S—


E-453
CH
N
4
4
Me
Me
H
—O—
—OCH2


E-454
CH
N
4
4
Me
Me
H
—O—
ssinglebondd


E-455
CH
N
4
4
Me
Me
H
—S—
—O—


E-456
CH
N
4
4
Me
Me
H
—CH2O—
—O—


E-457
CH
N
4
4
Me
Me
H
singlebond
—O—


E-458
CH
N
4
4
Me
Me
H
—S—
—S—


E-459
CH
N
4
4
Me
Me
H
—CH2O—
—OCH2


E-460
CH
N
4
4
Me
Me
H
singlebond
singlebond


E-461
CH
N
4
4
H
H
Me
—O—
—O—


E-462
CH
N
4
4
H
H
Me
—O—
—S—


E-463
CH
N
4
4
H
H
Me
—O—
—OCH2


E-464
CH
N
4
4
H
H
Me
—O—
singlebond


E-465
CH
N
4
4
H
H
Me
—S—
—O—


E-466
CH
N
4
4
H
H
Me
—CH2O—
—O—


E-467
CH
N
4
4
H
H
Me
singlebond
—O—


E-468
CH
N
4
4
H
H
Me
—S—
—S—


E-469
CH
N
4
4
H
H
Me
—CH2O—
—OCH2


E-470
CH
N
4
4
H
H
Me
singlebond
singlebond


E-471
CH
N
4
4
Ph
H
H
—O—
—O—


E-472
CH
N
4
4
Ph
H
H
—O—
—S—


E-473
CH
N
4
4
Ph
H
H
—O—
—OCH2


E-474
CH
N
4
4
Ph
H
H
—O—
singlebond


E-475
CH
N
4
4
Ph
H
H
—S—
—O—


E-476
CH
N
4
4
Ph
H
H
—CH2O—
—O—


E-477
CH
N
4
4
Ph
H
H
singlebond
—O—


E-478
CH
N
4
4
Ph
H
H
—S—
—S—


E-479
CH
N
4
4
Ph
H
H
—CH2O—
—OCH2


E-480
CH
N
4
4
Ph
H
H
singlebond
singlebond


E-481
CH
CH
2
5
H
H
H
—O—
—O—


E-482
CH
CH
3
5
H
H
H
—O—
—O—


E-483
CH
CH
5
2
H
H
H
—O—
—O—


E-484
CH
CH
5
3
H
H
H
—O—
—O—











embedded image


















TABLE 24





Com-











pound











No.
G1
G2
n
m
Ra
Rb
Rc
Q1
Q2







F-1
CH
CH
3
3
Me
H
H
—O—
—O—


F-2
CH
CH
3
3
Me
H
H
—O—
—S—


F-3
CH
CH
3
3
Me
H
H
—O—
—OCH2


F-4
CH
CH
3
3
Me
H
H
—O—
singlebond


F-5
CH
CH
3
3
Me
H
H
—S—
—O—


F-6
CH
CH
3
3
Me
H
H
—CH2O—
—O—


F-7
CH
CH
3
3
Me
H
H
singlebond
—O—


F-8
CH
CH
3
3
Me
H
H
—S—
—S—


F-9
CH
CH
3
3
Me
H
H
—CH2O—
—OCH2


F-10
CH
CH
3
3
Me
H
H
singlebond
singlebond


F-11
CH
CH
3
3
Me
Me
H
—O—
—O—


F-12
CH
CH
3
3
Me
Me
H
—O—
—S—


F-13
CH
CH
3
3
Me
Me
H
—O—
—OCH2


F-14
CH
CH
3
3
Me
Me
H
—O—
singlebond


F-15
CH
CH
3
3
Me
Me
H
—S—
—O—


F-16
CH
CH
3
3
Me
Me
H
—CH2O—
—O—


F-17
CH
CH
3
3
Me
Me
H
singlebond
—O—


F-18
CH
CH
3
3
Me
Me
H
—S—
—S—


F-19
CH
CH
3
3
Me
Me
H
—CH2O—
—OCH2


F-20
CH
CH
3
3
Me
Me
H
singlebond
singlebond


F-21
CH
CH
3
3
H
H
Me
—O—
—O—


F-22
CH
CH
3
3
H
H
Me
—O—
—S—


F-23
CH
CH
3
3
H
H
Me
—O—
—OCH2


F-24
CH
CH
3
3
H
H
Me
—O—
singlebond


F-25
CH
CH
3
3
H
H
Me
—S—
—O—


F-26
CH
CH
3
3
H
H
Me
—CH2O—
—O—


F-27
CH
CH
3
3
H
H
Me
singlebond
—O—


F-28
CH
CH
3
3
H
H
Me
—S—
—S—


F-29
CH
CH
3
3
H
H
Me
—CH2O—
—OCH2


F-30
CH
CH
3
3
H
H
Me
singlebond
singlebond


F-31
CH
CH
3
3
Ph
H
H
—O—
—O—


F-32
CH
CH
3
3
Ph
H
H
—O—
—S—


F-33
CH
CH
3
3
Ph
H
H
—O—
—OCH2


F-34
CH
CH
3
3
Ph
H
H
—O—
singlebond


F-35
CH
CH
3
3
Ph
H
H
—S—
—O—


F-36
CH
CH
3
3
Ph
H
H
—CH2O—
—O—


F-37
CH
CH
3
3
Ph
H
H
singlebond
—O—


F-38
CH
CH
3
3
Ph
H
H
—S—
—S—


F-39
CH
CH
3
3
Ph
H
H
—CH2O—
—OCH2


F-40
CH
CH
3
3
Ph
H
H
singlebond
singlebond


F-41
CH
CH
3
4
Me
H
H
—O—
—O—


F-42
CH
CH
3
4
Me
H
H
—O—
—S—


F-43
CH
CH
3
4
Me
H
H
—O—
—OCH2


F-44
CH
CH
3
4
Me
H
H
—O—
singlebond


F-45
CH
CH
3
4
Me
H
H
—S—
—O—


F-46
CH
CH
3
4
Me
H
H
—CH2O—
—O—


F-47
CH
CH
3
4
Me
H
H
singlebond
—O—


F-48
CH
CH
3
4
Me
H
H
—S—
—S—


F-49
CH
CH
3
4
Me
H
H
—CH2O—
—OCH2


F-50
CH
CH
3
4
Me
H
H
singlebond
singlebond


F-51
CH
CH
3
4
Me
Me
H
—O—
—O—


F-52
CH
CH
3
4
Me
Me
H
—O—
—S—


F-53
CH
CH
3
4
Me
Me
H
—O—
—OCH2


F-54
CH
CH
3
4
Me
Me
H
—O—
singlebond


F-55
CH
CH
3
4
Me
Me
H
—S—
—O—


F-56
CH
CH
3
4
Me
Me
H
—CH2O—
—O—


F-57
CH
CH
3
4
Me
Me
H
singlebond
—O—


F-58
CH
CH
3
4
Me
Me
H
—S—
—S—


F-59
CH
CH
3
4
Me
Me
H
—CH2O—
—OCH2


F-60
CH
CH
3
4
Me
Me
H
singlebond
singlebond


F-61
CH
CH
3
4
H
H
Me
—O—
—O—


F-62
CH
CH
3
4
H
H
Me
—O—
—S—


F-63
CH
CH
3
4
H
H
Me
—O—
—OCH2


F-64
CH
CH
3
4
H
H
Me
—O—
singlebond


F-65
CH
CH
3
4
H
H
Me
—S—
—O—


F-66
CH
CH
3
4
H
H
Me
—CH2O—
—O—


F-67
CH
CH
3
4
H
H
Me
singlebond
—O—


F-68
CH
CH
3
4
H
H
Me
—S—
—S—


F-69
CH
CH
3
4
H
H
Me
—CH2O—
—OCH2


F-70
CH
CH
3
4
H
H
Me
singlebond
singlebond


F-71
CH
CH
3
4
Ph
H
H
—O—
—O—


F-72
CH
CH
3
4
Ph
H
H
—O—
—S—


F-73
CH
CH
3
4
Ph
H
H
—O—
—OCH2


F-74
CH
CH
3
4
Ph
H
H
—O—
singlebond


F-75
CH
CH
3
4
Ph
H
H
—S—
—O—


F-76
CH
CH
3
4
Ph
H
H
—CH2O—
—O—


F-77
CH
CH
3
4
Ph
H
H
singlebond
—O—


F-78
CH
CH
3
4
Ph
H
H
—S—
—S—


F-79
CH
CH
3
4
Ph
H
H
—CH2O—
—OCH2


F-80
CH
CH
3
4
Ph
H
H
singlebond
singlebond


F-81
CH
CH
4
3
Me
H
H
—O—
—O—


F-82
CH
CH
4
3
Me
H
H
—O—
—S—


F-83
CH
CH
4
3
Me
H
H
—O—
—OCH2


F-84
CH
CH
4
3
Me
H
H
—O—
singlebond


F-85
CH
CH
4
3
Me
H
H
—S—
—O—


F-86
CH
CH
4
3
Me
H
H
—CH2O—
—O—


F-87
CH
CH
4
3
Me
H
H
singlebond
—O—


F-88
CH
CH
4
3
Me
H
H
—S—
—S—


F-89
CH
CH
4
3
Me
H
H
—CH2O—
—OCH2


F-90
CH
CH
4
3
Me
H
H
singlebond
singlebond


F-91
CH
CH
4
3
Me
Me
H
—O—
—O—


F-92
CH
CH
4
3
Me
Me
H
—O—
—S—


F-93
CH
CH
4
3
Me
Me
H
—O—
—OCH2


F-94
CH
CH
4
3
Me
Me
H
—O—
singlebond


F-95
CH
CH
4
3
Me
Me
H
—S—
—O—


F-96
CH
CH
4
3
Me
Me
H
—CH2O—
—O—


F-97
CH
CH
4
3
Me
Me
H
singlebond
—O—


F-98
CH
CH
4
3
Me
Me
H
—S—
—S—


F-99
CH
CH
4
3
Me
Me
H
—CH2O—
—OCH2


F-100
CH
CH
4
3
Me
Me
H
singlebond
singlebond


F-101
CH
CH
4
3
H
H
Me
—O—
—O—


F-102
CH
CH
4
3
H
H
Me
—O—
—S—


F-103
CH
CH
4
3
H
H
Me
—O—
—OCH2


F-104
CH
CH
4
3
H
H
Me
—O—
singlebond


F-105
CH
CH
4
3
H
H
Me
—S—
—O—


F-106
CH
CH
4
3
H
H
Me
—CH2O—
—O—


F-107
CH
CH
4
3
H
H
Me
singlebond
—O—


F-108
CH
CH
4
3
H
H
Me
—S—
—S—


F-109
CH
CH
4
3
H
H
Me
—CH2O—
—OCH2


F-110
CH
CH
4
3
H
H
Me
singlebond
singlebond

























TABLE 25





Com-











pound











No.
G1
G2
n
m
Ra
Rb
Rc
Q1
Q2







F-111
CH
CH
4
3
Ph
H
H
—O—
—O—


F-112
CH
CH
4
3
Ph
H
H
—O—
—S—


F-113
CH
CH
4
3
Ph
H
H
—O—
—OCH2


F-114
CH
CH
4
3
Ph
H
H
—O—
singlebond


F-115
CH
CH
4
3
Ph
H
H
—S—
—O—


F-116
CH
CH
4
3
Ph
H
H
—CH2O—
—O—


F-117
CH
CH
4
3
Ph
H
H
singlebond
—O—


F-118
CH
CH
4
3
Ph
H
H
—S—
—S—


F-119
CH
CH
4
3
Ph
H
H
—CH2O—
—OCH2


F-120
CH
CH
4
3
Ph
H
H
singlebond
singlebond


F-121
CH
CH
4
4
Me
H
H
—O—
—O—


F-122
CH
CH
4
4
Me
H
H
—O—
—S—


F-123
CH
CH
4
4
Me
H
H
—O—
—OCH2


F-124
CH
CH
4
4
Me
H
H
—O—
singlebond


F-125
CH
CH
4
4
Me
H
H
—S—
—O—


F-126
CH
CH
4
4
Me
H
H
—CH2O—
—O—


F-127
CH
CH
4
4
Me
H
H
singlebond
—O—


F-128
CH
CH
4
4
Me
H
H
—S—
—S—


F-129
CH
CH
4
4
Me
H
H
—CH2O—
—OCH2


F-130
CH
CH
4
4
Me
H
H
singlebond
singlebond


F-131
CH
CH
4
4
Me
Me
H
—O—
—O—


F-132
CH
CH
4
4
Me
Me
H
—O—
—S—


F-133
CH
CH
4
4
Me
Me
H
—O—
—OCH2


F-134
CH
CH
4
4
Me
Me
H
—O—
singlebond


F-135
CH
CH
4
4
Me
Me
H
—S—
—O—


F-136
CH
CH
4
4
Me
Me
H
—CH2O—
—O—


F-137
CH
CH
4
4
Me
Me
H
singlebond
—O—


F-138
CH
CH
4
4
Me
Me
H
—S—
—S—


F-139
CH
CH
4
4
Me
Me
H
—CH2O—
—OCH2


F-140
CH
CH
4
4
Me
Me
H
singlebond
singlebond


F-141
CH
CH
4
4
H
H
Me
—O—
—O—


F-142
CH
CH
4
4
H
H
Me
—O—
—S—


F-143
CH
CH
4
4
H
H
Me
—O—
—OCH2


F-144
CH
CH
4
4
H
H
Me
—O—
singlebond


F-145
CH
CH
4
4
H
H
Me
—S—
—O—


F-146
CH
CH
4
4
H
H
Me
—CH2O—
—O—


F-147
CH
CH
4
4
H
H
Me
singlebond
—O—


F-148
CH
CH
4
4
H
H
Me
—S—
—S—


F-149
CH
CH
4
4
H
H
Me
—CH2O—
—OCH2


F-150
CH
CH
4
4
H
H
Me
singlebond
singlebond


F-151
CH
CH
4
4
Ph
H
H
—O—
—O—


F-152
CH
CH
4
4
Ph
H
H
—O—
—S—


F-153
CH
CH
4
4
Ph
H
H
—O—
—OCH2


F-154
CH
CH
4
4
Ph
H
H
—O—
singlebond


F-155
CH
CH
4
4
Ph
H
H
—S—
—O—


F-156
CH
CH
4
4
Ph
H
H
—CH2O—
—O—


F-157
CH
CH
4
4
Ph
H
H
singlebond
—O—


F-158
CH
CH
4
4
Ph
H
H
—S—
—S—


F-159
CH
CH
4
4
Ph
H
H
—CH2O—
—OCH2


F-160
CH
CH
4
4
Ph
H
H
singlebond
singlebond


F-161
N
CH
3
3
Me
H
H
—O—
—O—


F-162
N
CH
3
3
Me
H
H
—O—
—S—


F-163
N
CH
3
3
Me
H
H
—O—
—OCH2


F-164
N
CH
3
3
Me
H
H
—O—
singlebond


F-165
N
CH
3
3
Me
H
H
—S—
—O—


F-166
N
CH
3
3
Me
H
H
—CH2O—
—O—


F-167
N
CH
3
3
Me
H
H
singlebond
—O—


F-168
N
CH
3
3
Me
H
H
—S—
—S—


F-169
N
CH
3
3
Me
H
H
—CH2O—
—OCH2


F-170
N
CH
3
3
Me
H
H
singlebond
singlebond


F-171
N
CH
3
3
Me
Me
H
—O—
—O—


F-172
N
CH
3
3
Me
Me
H
—O—
—S—


F-173
N
CH
3
3
Me
Me
H
—O—
—OCH2


F-174
N
CH
3
3
Me
Me
H
—O—
singlebond


F-175
N
CH
3
3
Me
Me
H
—S—
—O—


F-176
N
CH
3
3
Me
Me
H
—CH2O—
—O—


F-177
N
CH
3
3
Me
Me
H
singlebond
—O—


F-178
N
CH
3
3
Me
Me
H
—S—
—S—


F-179
N
CH
3
3
Me
Me
H
—CH2O—
—OCH2


F-180
N
CH
3
3
Me
Me
H
singlebond
singlebond


F-181
N
CH
3
3
H
H
Me
—O—
—O—


F-182
N
CH
3
3
H
H
Me
—O—
—S—


F-183
N
CH
3
3
H
H
Me
—O—
—OCH2


F-184
N
CH
3
3
H
H
Me
—O—
singlebond


F-185
N
CH
3
3
H
H
Me
—S—
—O—


F-186
N
CH
3
3
H
H
Me
—CH2O—
—O—


F-187
N
CH
3
3
H
H
Me
singlebond
—O—


F-188
N
CH
3
3
H
H
Me
—S—
—S—


F-189
N
CH
3
3
H
H
Me
—CH2O—
—OCH2


F-190
N
CH
3
3
H
H
Me
singlebond
singlebond


F-191
N
CH
3
3
Ph
H
H
—O—
—O—


F-192
N
CH
3
3
Ph
H
H
—O—
—S—


F-193
N
CH
3
3
Ph
H
H
—O—
—OCH2


F-194
N
CH
3
3
Ph
H
H
—O—
singlebond


F-195
N
CH
3
3
Ph
H
H
—S—
—O—


F-196
N
CH
3
3
Ph
H
H
—CH2O—
—O—


F-197
N
CH
3
3
Ph
H
H
singlebond
—O—


F-198
N
CH
3
3
Ph
H
H
—S—
—S—


F-199
N
CH
3
3
Ph
H
H
—CH2O—
—OCH2


F-200
N
CH
3
3
Ph
H
H
singlebond
singlebond


F-201
N
CH
3
4
Me
H
H
—O—
—O—


F-202
N
CH
3
4
Me
H
H
—O—
—S—


F-203
N
CH
3
4
Me
H
H
—O—
—OCH2


F-204
N
CH
3
4
Me
H
H
—O—
singlebond


F-205
N
CH
3
4
Me
H
H
—S—
—O—


F-206
N
CH
3
4
Me
H
H
—CH2O—
—O—


F-207
N
CH
3
4
Me
H
H
singlebond
—O—


F-208
N
CH
3
4
Me
H
H
—S—
—S—


F-209
N
CH
3
4
Me
H
H
—CH2O—
—OCH2


F-210
N
CH
3
4
Me
H
H
singlebond
singlebond


F-211
N
CH
3
4
Me
Me
H
—O—
—O—


F-212
N
CH
3
4
Me
Me
H
—O—
—S—


F-213
N
CH
3
4
Me
Me
H
—O—
—OCH2


F-214
N
CH
3
4
Me
Me
H
—O—
singlebond


F-215
N
CH
3
4
Me
Me
H
—S—
—O—


F-216
N
CH
3
4
Me
Me
H
—CH2O—
—O—


F-217
N
CH
3
4
Me
Me
H
singlebond
—O—


F-218
N
CH
3
4
Me
Me
H
—S—
—S—


F-219
N
CH
3
4
Me
Me
H
—CH2O—
—OCH2


F-220
N
CH
3
4
Me
Me
H
singlebond
singlebond

























TABLE 26





Com-











pound











No.
G1
G2
n
m
Ra
Rb
Rc
Q1
Q2







F-221
N
CH
3
4
H
H
Me
—O—
—O—


F-222
N
CH
3
4
H
H
Me
—O—
—S—


F-223
N
CH
3
4
H
H
Me
—O—
—OCH2


F-224
N
CH
3
4
H
H
Me
—O—
singlebond


F-225
N
CH
3
4
H
H
Me
—S—
—O—


F-226
N
CH
3
4
H
H
Me
—CH2O—
—O—


F-227
N
CH
3
4
H
H
Me
singlebond
—O—


F-228
N
CH
3
4
H
H
Me
—S—
—S—


F-229
N
CH
3
4
H
H
Me
—CH2O—
—OCH2


F-230
N
CH
3
4
H
H
Me
singlebond
singlebond


F-231
N
CH
3
4
Ph
H
H
—O—
—O—


F-232
N
CH
3
4
Ph
H
H
—O—
—S—


F-233
N
CH
3
4
Ph
H
H
—O—
—OCH2


F-234
N
CH
3
4
Ph
H
H
—O—
singlebond


F-235
N
CH
3
4
Ph
H
H
—S—
—O—


F-236
N
CH
3
4
Ph
H
H
—CH2O—
—O—


F-237
N
CH
3
4
Ph
H
H
singlebond
—O—


F-238
N
CH
3
4
Ph
H
H
—S—
—S—


F-239
N
CH
3
4
Ph
H
H
—CH2O—
—OCH2


F-240
N
CH
3
4
Ph
H
H
singlebond
singlebond


F-241
N
CH
4
3
Me
H
H
—O—
—O—


F-242
N
CH
4
3
Me
H
H
—O—
—S—


F-243
N
CH
4
3
Me
H
H
—O—
—OCH2


F-244
N
CH
4
3
Me
H
H
—O—
singlebond


F-245
N
CH
4
3
Me
H
H
—S—
—O—


F-246
N
CH
4
3
Me
H
H
—CH2O—
—O—


F-247
N
CH
4
3
Me
H
H
singlebond
—O—


F-248
N
CH
4
3
Me
H
H
—S—
—S—


F-249
N
CH
4
3
Me
H
H
—CH2O—
—OCH2


F-250
N
CH
4
3
Me
H
H
singlebond
singlebond


F-251
N
CH
4
3
Me
Me
H
—O—
—O—


F-252
N
CH
4
3
Me
Me
H
—O—
—S—


F-253
N
CH
4
3
Me
Me
H
—O—
—OCH2


F-254
N
CH
4
3
Me
Me
H
—O—
singlebond


F-255
N
CH
4
3
Me
Me
H
—S—
—O—


F-256
N
CH
4
3
Me
Me
H
—CH2O—
—O—


F-257
N
CH
4
3
Me
Me
H
singlebond
—O—


F-258
N
CH
4
3
Me
Me
H
—S—
—S—


F-259
N
CH
4
3
Me
Me
H
—CH2O—
—OCH2


F-260
N
CH
4
3
Me
Me
H
singlebond
singlebond


F-261
N
CH
4
3
H
H
Me
—O—
—O—


F-262
N
CH
4
3
H
H
Me
—O—
—S—


F-263
N
CH
4
3
H
H
Me
—O—
—OCH2


F-264
N
CH
4
3
H
H
Me
—O—
singlebond


F-265
N
CH
4
3
H
H
Me
—S—
—O—


F-266
N
CH
4
3
H
H
Me
—CH2O—
—O—


F-267
N
CH
4
3
H
H
Me
singlebond
—O—


F-268
N
CH
4
3
H
H
Me
—S—
—S—


F-269
N
CH
4
3
H
H
Me
—CH2O—
—OCH2


F-270
N
CH
4
3
H
H
Me
singlebond
singlebond


F-271
N
CH
4
3
Ph
H
H
—O—
—O—


F-272
N
CH
4
3
Ph
H
H
—O—
—S—


F-273
N
CH
4
3
Ph
H
H
—O—
—OCH2


F-274
N
CH
4
3
Ph
H
H
—O—
singlebond


F-275
N
CH
4
3
Ph
H
H
—S—
—O—


F-276
N
CH
4
3
Ph
H
H
—CH2O—
—O—


F-277
N
CH
4
3
Ph
H
H
singlebond
—O—


F-278
N
CH
4
3
Ph
H
H
—S—
—S—


F-279
N
CH
4
3
Ph
H
H
—CH2O—
—OCH2


F-280
N
CH
4
3
Ph
H
H
singlebond
singlebond


F-281
N
CH
4
4
Me
H
H
—O—
—O—


F-282
N
CH
4
4
Me
H
H
—O—
—S—


F-283
N
CH
4
4
Me
H
H
—O—
—OCH2


F-284
N
CH
4
4
Me
H
H
—O—
singlebond


F-285
N
CH
4
4
Me
H
H
—S—
—O—


F-286
N
CH
4
4
Me
H
H
—CH2O—
—O—


F-287
N
CH
4
4
Me
H
H
singlebond
—O—


F-288
N
CH
4
4
Me
H
H
—S—
—S—


F-289
N
CH
4
4
Me
H
H
—CH2O—
—OCH2


F-290
N
CH
4
4
Me
H
H
singlebond
singlebond


F-291
N
CH
4
4
Me
Me
H
—O—
—O—


F-292
N
CH
4
4
Me
Me
H
—O—
—S—


F-293
N
CH
4
4
Me
Me
H
—O—
—OCH2


F-294
N
CH
4
4
Me
Me
H
—O—
singlebond


F-295
N
CH
4
4
Me
Me
H
—S—
—O—


F-296
N
CH
4
4
Me
Me
H
—CH2O—
—O—


F-297
N
CH
4
4
Me
Me
H
singlebond
—O—


F-298
N
CH
4
4
Me
Me
H
—S—
—S—


F-299
N
CH
4
4
Me
Me
H
—CH2O—
—OCH2


F-300
N
CH
4
4
Me
Me
H
singlebond
singlebond


F-301
N
CH
4
4
H
H
Me
—O—
—O—


F-302
N
CH
4
4
H
H
Me
—O—
—S—


F-303
N
CH
4
4
H
H
Me
—O—
—OCH2


F-304
N
CH
4
4
H
H
Me
—O—
singlebond


F-305
N
CH
4
4
H
H
Me
—S—
—O—


F-306
N
CH
4
4
H
H
Me
—CH2O—
—O—


F-307
N
CH
4
4
H
H
Me
singlebond
—O—


F-308
N
CH
4
4
H
H
Me
—S—
—S—


F-309
N
CH
4
4
H
H
Me
—CH2O—
—OCH2


F-310
N
CH
4
4
H
H
Me
singlebond
singlebond


F-311
N
CH
4
4
Ph
H
H
—O—
—O—


F-312
N
CH
4
4
Ph
H
H
—O—
—S—


F-313
N
CH
4
4
Ph
H
H
—O—
—OCH2


F-314
N
CH
4
4
Ph
H
H
—O—
singlebond


F-315
N
CH
4
4
Ph
H
H
—S—
—O—


F-316
N
CH
4
4
Ph
H
H
—CH2O—
—O—


F-317
N
CH
4
4
Ph
H
H
singlebond
—O—


F-318
N
CH
4
4
Ph
H
H
—S—
—S—


F-319
N
CH
4
4
Ph
H
H
—CH2O—
—OCH2


F-320
N
CH
4
4
Ph
H
H
singlebond
singlebond


F-321
CH
N
3
3
Me
H
H
—O—
—O—


F-322
CH
N
3
3
Me
H
H
—O—
—S—


F-323
CH
N
3
3
Me
H
H
—O—
—OCH2


F-324
CH
N
3
3
Me
H
H
—O—
singlebond


F-325
CH
N
3
3
Me
H
H
—S—
—O—


F-326
CH
N
3
3
Me
H
H
—CH2O—
—O—


F-327
CH
N
3
3
Me
H
H
singlebond
—O—


F-328
CH
N
3
3
Me
H
H
—S—
—S—


F-329
CH
N
3
3
Me
H
H
—CH2O—
—OCH2


F-330
CH
N
3
3
Me
H
H
singlebond
singlebond

























TABLE 27





Com-











pound











No.
G1
G2
n
m
Ra
Rb
Rc
Q1
Q2







F-331
CH
N
3
3
Me
Me
H
—O—
—O—


F-332
CH
N
3
3
Me
Me
H
—O—
—S—


F-333
CH
N
3
3
Me
Me
H
—O—
—OCH2


F-334
CH
N
3
3
Me
Me
H
—O—
singlebond


F-335
CH
N
3
3
Me
Me
H
—S—
—O—


F-336
CH
N
3
3
Me
Me
H
—CH2O—
—O—


F-337
CH
N
3
3
Me
Me
H
singlebond
—O—


F-338
CH
N
3
3
Me
Me
H
—S—
—S—


F-339
CH
N
3
3
Me
Me
H
—CH2O—
—OCH2


F-340
CH
N
3
3
Me
Me
H
singlebond
singlebond


F-341
CH
N
3
3
H
H
Me
—O—
—O—


F-342
CH
N
3
3
H
H
Me
—O—
—S—


F-343
CH
N
3
3
H
H
Me
—O—
—OCH2


F-344
CH
N
3
3
H
H
Me
—O—
singlebond


F-345
CH
N
3
3
H
H
Me
—S—
—O—


F-346
CH
N
3
3
H
H
Me
—CH2O—
—O—


F-347
CH
N
3
3
H
H
Me
singlebond
—O—


F-348
CH
N
3
3
H
H
Me
—S—
—S—


F-349
CH
N
3
3
H
H
Me
—CH2O—
—OCH2


F-350
CH
N
3
3
H
H
Me
singlebond
singlebond


F-351
CH
N
3
3
Ph
H
H
—O—
—O—


F-352
CH
N
3
3
Ph
H
H
—O—
—S—


F-353
CH
N
3
3
Ph
H
H
—O—
—OCH2


F-354
CH
N
3
3
Ph
H
H
—O—
singlebond


F-355
CH
N
3
3
Ph
H
H
—S—
—O—


F-356
CH
N
3
3
Ph
H
H
—CH2O—
—O—


F-357
CH
N
3
3
Ph
H
H
singlebond
—O—


F-358
CH
N
3
3
Ph
H
H
—S—
—S—


F-359
CH
N
3
3
Ph
H
H
—CH2O—
—OCH2


F-360
CH
N
3
3
Ph
H
H
singlebond
singlebond


F-361
CH
N
3
4
Me
H
H
—O—
—O—


F-362
CH
N
3
4
Me
H
H
—O—
—S—


F-363
CH
N
3
4
Me
H
H
—O—
—OCH2


F-364
CH
N
3
4
Me
H
H
—O—
singlebond


F-365
CH
N
3
4
Me
H
H
—S—
—O—


F-366
CH
N
3
4
Me
H
H
—CH2O—
—O—


F-367
CH
N
3
4
Me
H
H
singlebond
—O—


F-368
CH
N
3
4
Me
H
H
—S—
—S—


F-369
CH
N
3
4
Me
H
H
—CH2O—
—OCH2


F-370
CH
N
3
4
Me
H
H
singlebond
singlebond


F-371
CH
N
3
4
Me
Me
H
—O—
—O—


F-372
CH
N
3
4
Me
Me
H
—O—
—S—


F-373
CH
N
3
4
Me
Me
H
—O—
—OCH2


F-374
CH
N
3
4
Me
Me
H
—O—
singlebond


F-375
CH
N
3
4
Me
Me
H
—S—
—O—


F-376
CH
N
3
4
Me
Me
H
—CH2O—
—O—


F-377
CH
N
3
4
Me
Me
H
singlebond
—O—


F-378
CH
N
3
4
Me
Me
H
—S—
—S—


F-379
CH
N
3
4
Me
Me
H
—CH2O—
—OCH2


F-380
CH
N
3
4
Me
Me
H
singlebond
singlebond


F-381
CH
N
3
4
H
H
Me
—O—
—O—


F-382
CH
N
3
4
H
H
Me
—O—
—S—


F-383
CH
N
3
4
H
H
Me
—O—
—OCH2


F-384
CH
N
3
4
H
H
Me
—O—
singlebond


F-385
CH
N
3
4
H
H
Me
—S—
—O—


F-386
CH
N
3
4
H
H
Me
—CH2O—
—O—


F-387
CH
N
3
4
H
H
Me
singlebond
—O—


F-388
CH
N
3
4
H
H
Me
—S—
—S—


F-389
CH
N
3
4
H
H
Me
—CH2O—
—OCH2


F-390
CH
N
3
4
H
H
Me
singlebond
singlebond


F-391
CH
N
3
4
Ph
H
H
—O—
—O—


F-392
CH
N
3
4
Ph
H
H
—O—
—S—


F-393
CH
N
3
4
Ph
H
H
—O—
—OCH2


F-394
CH
N
3
4
Ph
H
H
—O—
singlebond


F-395
CH
N
3
4
Ph
H
H
—S—
—O—


F-396
CH
N
3
4
Ph
H
H
—CH2O—
—O—


F-397
CH
N
3
4
Ph
H
H
singlebond
—O—


F-398
CH
N
3
4
Ph
H
H
—S—
—S—


F-399
CH
N
3
4
Ph
H
H
—CH2O—
—OCH2


F-400
CH
N
3
4
Ph
H
H
singlebond
singlebond


F-401
CH
N
4
3
Me
H
H
—O—
—O—


F-402
CH
N
4
3
Me
H
H
—O—
—S—


F-403
CH
N
4
3
Me
H
H
—O—
—OCH2


F-404
CH
N
4
3
Me
H
H
—O—
singlebond


F-405
CH
N
4
3
Me
H
H
—S—
—O—


F-406
CH
N
4
3
Me
H
H
—CH2O—
—O—


F-407
CH
N
4
3
Me
H
H
singlebond
—O—


F-408
CH
N
4
3
Me
H
H
—S—
—S—


F-409
CH
N
4
3
Me
H
H
—CH2O—
—OCH2


F-410
CH
N
4
3
Me
H
H
singlebond
singlebond


F-411
CH
N
4
3
Me
Me
H
—O—
—O—


F-412
CH
N
4
3
Me
Me
H
—O—
—S—


F-413
CH
N
4
3
Me
Me
H
—O—
—OCH2


F-414
CH
N
4
3
Me
Me
H
—O—
singlebond


F-415
CH
N
4
3
Me
Me
H
—S—
—O—


F-416
CH
N
4
3
Me
Me
H
—CH2O—
—O—


F-417
CH
N
4
3
Me
Me
H
singlebond
—O—


F-418
CH
N
4
3
Me
Me
H
—S—
—S—


F-419
CH
N
4
3
Me
Me
H
—CH2O—
—OCH2


F-420
CH
N
4
3
Me
Me
H
singlebond
singlebond


F-421
CH
N
4
3
H
H
Me
—O—
—O—


F-422
CH
N
4
3
H
H
Me
—O—
—S—


F-423
CH
N
4
3
H
H
Me
—O—
—OCH2


F-424
CH
N
4
3
H
H
Me
—O—
singlebond


F-425
CH
N
4
3
H
H
Me
—S—
—O—


F-426
CH
N
4
3
H
H
Me
—CH2O—
—O—


F-427
CH
N
4
3
H
H
Me
singlebond
—O—


F-428
CH
N
4
3
H
H
Me
—S—
—S—


F-429
CH
N
4
3
H
H
Me
—CH2O—
—OCH2


F-430
CH
N
4
3
H
H
Me
singlebond
singlebond


F-431
CH
N
4
3
Ph
H
H
—O—
—O—


F-432
CH
N
4
3
Ph
H
H
—O—
—S—


F-433
CH
N
4
3
Ph
H
H
—O—
—OCH2


F-434
CH
N
4
3
Ph
H
H
—O—
singlebond


F-435
CH
N
4
3
Ph
H
H
—S—
—O—


F-436
CH
N
4
3
Ph
H
H
—CH2O—
—O—


F-437
CH
N
4
3
Ph
H
H
singlebond
—O—


F-438
CH
N
4
3
Ph
H
H
—S—
—S—


F-439
CH
N
4
3
Ph
H
H
—CH2O—
—OCH2


F-440
CH
N
4
3
Ph
H
H
singlebond
singlebond

























TABLE 28





Com-











pound











No.
G1
G2
n
m
Ra
Rb
Rc
Q1
Q2







F-441
CH
N
4
4
Me
H
H
—O—
—O—


F-442
CH
N
4
4
Me
H
H
—O—
—S—


F-443
CH
N
4
4
Me
H
H
—O—
—OCH2


F-444
CH
N
4
4
Me
H
H
—O—
singlebond


F-445
CH
N
4
4
Me
H
H
—S—
—O—


F-446
CH
N
4
4
Me
H
H
—CH2O—
—O—


F-447
CH
N
4
4
Me
H
H
singlebond
—O—


F-448
CH
N
4
4
Me
H
H
—S—
—S—


F-449
CH
N
4
4
Me
H
H
—CH2O—
—OCH2


F-450
CH
N
4
4
Me
H
H
singlebond
singlebond


F-451
CH
N
4
4
Me
Me
H
—O—
—O—


F-452
CH
N
4
4
Me
Me
H
—O—
—S—


F-453
CH
N
4
4
Me
Me
H
—O—
—OCH2


F-454
CH
N
4
4
Me
Me
H
—O—
singlebond


F-455
CH
N
4
4
Me
Me
H
—S—
—O—


F-456
CH
N
4
4
Me
Me
H
—CH2O—
—O—


F-457
CH
N
4
4
Me
Me
H
singlebond
—O—


F-458
CH
N
4
4
Me
Me
H
—S—
—S—


F-459
CH
N
4
4
Me
Me
H
—CH2O—
—OCH2


F-460
CH
N
4
4
Me
Me
H
singlebond
singlebond


F-461
CH
N
4
4
H
H
Me
—O—
—O—


F-462
CH
N
4
4
H
H
Me
—O—
—S—


F-463
CH
N
4
4
H
H
Me
—O—
—OCH2


F-464
CH
N
4
4
H
H
Me
—O—
singlebond


F-465
CH
N
4
4
H
H
Me
—S—
—O—


F-466
CH
N
4
4
H
H
Me
—CH2O—
—O—


F-467
CH
N
4
4
H
H
Me
singlebond
—O—


F-468
CH
N
4
4
H
H
Me
—S—
—S—


F-469
CH
N
4
4
H
H
Me
—CH2O—
—OCH2


F-470
CH
N
4
4
H
H
Me
singlebond
singlebond


F-471
CH
N
4
4
Ph
H
H
—O—
—O—


F-472
CH
N
4
4
Ph
H
H
—O—
—S—


F-473
CH
N
4
4
Ph
H
H
—O—
—OCH2


F-474
CH
N
4
4
Ph
H
H
—O—
singlebond


F-475
CH
N
4
4
Ph
H
H
—S—
—O—


F-476
CH
N
4
4
Ph
H
H
—CH2O—
—O—


F-477
CH
N
4
4
Ph
H
H
singlebond
—O—


F-478
CH
N
4
4
Ph
H
H
—S—
—S—


F-479
CH
N
4
4
Ph
H
H
—CH2O—
—OCH2


F-480
CH
N
4
4
Ph
H
H
singlebond
singlebond


F-481
CH
CH
2
5
H
H
H
—O—
—O—


F-482
CH
CH
3
5
H
H
H
—O—
—O—


F-483
CH
CH
5
2
H
H
H
—O—
—O—


F-484
CH
CH
5
3
H
H
H
—O—
—O—











embedded image















TABLE 29





Com-








pound








No.
Ra
Rb
Rc
n
m
W







G-1  G-2  G-3  G-4  G-5 
Me Me Me Me Me
H H H H H
H H H H H
6 6 6 6 7
6 7 8 9 6


embedded image




G-6 
Me
H
H
7
7



G-7 
Me
H
H
7
8



G-8 
Me
H
H
7
9



G-9 
Me
H
H
8
6



G-10
Me
H
H
8
7



G-11
Me
H
H
8
8



G-12
Me
H
H
8
9



G-13
Me
H
H
9
6



G-14
Me
H
H
9
7



G-15
Me
H
H
9
8



G-16
Me
H
H
9
9



G-17
H
H
Me
6
6



G-18
H
H
Me
6
7



G-19
H
H
Me
6
8



G-20
H
H
Me
6
9



G-21
H
H
Me
7
6



G-22
H
H
Me
7
7



G-23
H
H
Me
7
8



G-24
H
H
Me
7
9



G-25
H
H
Me
8
6



G-26
H
H
Me
8
7



G-27
H
H
Me
8
8



G-28
H
H
Me
8
9



G-29
H
H
Me
9
6



G-30
H
H
Me
9
7



G-31
H
H
Me
9
8



G-32
H
H
Me
9
9



G-33
Me
Me
H
6
6



G-34
Me
Me
H
6
7



G-35
Me
Me
H
6
8



G-36
Me
Me
H
6
9



G-37
Me
Me
H
7
6



G-38
Me
Me
H
7
7



G-39
Me
Me
H
7
8



G-40
Me
Me
H
7
9



G-41
Me
Me
H
8
6



G-42
Me
Me
H
8
7



G-43
Me
Me
H
8
8



G-44
Me
Me
H
8
9



G-45
Me
Me
H
9
6



G-46
Me
Me
H
9
7



G-47
Me
Me
H
9
8



G-48
Me
Me
H
9
9



G-49
H
Me
Me
6
6



G-50
H
Me
Me
6
7



G-51
H
Me
Me
6
8



G-52
H
Me
Me
6
9



G-53
H
Me
Me
7
6



G-54
H
Me
Me
7
7



G-55
H
Me
Me
7
8



G-56 G-57 G-58 G-59
H H H H
Me Me Me Me
Me Me Me Me
7 8 8 8
9 6 7 8



G-60
H
Me
Me
8
9



G-61
H
Me
Me
9
6



G-62
H
Me
Me
9
7



G-63
H
Me
Me
9
8



G-64
H
Me
Me
9
9



G-65
Me
Me
Me
6
6



G-66
Me
Me
Me
6
7



G-67
Me
Me
Me
6
8



G-68
Me
Me
Me
6
9



G-69
Me
Me
Me
7
6



G-70
Me
Me
Me
7
7



G-71
Me
Me
Me
7
8



G-72
Me
Me
Me
7
9



G-73
Me
Me
Me
8
6



G-74
Me
Me
Me
8
7



G-75
Me
Me
Me
8
8



G-76
Me
Me
Me
8
9



G-77
Me
Me
Me
9
6



G-78
Me
Me
Me
9
7



G-79
Me
Me
Me
9
8



G-80
Me
Me
Me
9
9



G-81 G-82 G-83 G-84 G-85
Me Me Me Me Me
H H H H H
H H H H H
6 6 6 6 7
6 7 8 9 6


embedded image




G-86
Me
H
H
7
7



G-87
Me
H
H
7
8



G-88
Me
H
H
7
9



G-89
Me
H
H
8
6



G-90
Me
H
H
8
7



G-91
Me
H
H
8
8



G-92
Me
H
H
8
9



G-93
Me
H
H
9
6



G-94
Me
H
H
9
7



G-95
Me
H
H
9
8



G-96
Me
H
H
9
9



G-97
H
H
Me
6
6



G-98
H
H
Me
6
7



G-99
H
H
Me
6
8



 G-100
H
H
Me
6
9



 G-101
H
H
Me
7
6



 G-102
H
H
Me
7
7



 G-103
H
H
Me
7
8



 G-104
H
H
Me
7
9



 G-105
H
H
Me
8
6



 G-106
H
H
Me
8
7



 G-107
H
H
Me
8
8



 G-108
H
H
Me
8
9



 G-109
H
H
Me
9
6



 G-110
H
H
Me
9
7






















TABLE 30





Com-








pound








No.
Ra
Rb
Rc
n
m
W







G-111 G-112 G-113 G-114 G-115
H H Me Me Me
H H Me Me Me
Me Me H H H
9 9 6 6 6
8 9 6 7 8


embedded image




G-116
Me
Me
H
6
9



G-117
Me
Me
H
7
6



G-118
Me
Me
H
7
7



G-119
Me
Me
H
7
8



G-120
Me
Me
H
7
9



G-121
Me
Me
H
8
6



G-122
Me
Me
H
8
7



G-123
Me
Me
H
8
8



G-124
Me
Me
H
8
9



G-125
Me
Me
H
9
6



G-126
Me
Me
H
9
7



G-127
Me
Me
H
9
8



G-128
Me
Me
H
9
9



G-129
H
Me
Me
6
6



G-130
H
Me
Me
6
7



G-131
H
Me
Me
6
8



G-132
H
Me
Me
6
9



G-133
H
Me
Me
7
6



G-134
H
Me
Me
7
7



G-135
H
Me
Me
7
8



G-136
H
Me
Me
7
9



G-137
H
Me
Me
8
6



G-138
H
Me
Me
8
7



G-139
H
Me
Me
8
8



G-140
H
Me
Me
8
9



G-141
H
Me
Me
9
6



G-142
H
Me
Me
9
7



G-143
H
Me
Me
9
8



G-144
H
Me
Me
9
9



G-145
Me
Me
Me
6
6



G-146
Me
Me
Me
6
7



G-147
Me
Me
Me
6
8



G-148
Me
Me
Me
6
9



G-149
Me
Me
Me
7
6



G-150
Me
Me
Me
7
7



G-151
Me
Me
Me
7
8



G-152
Me
Me
Me
7
9



G-153
Me
Me
Me
8
6



G-154
Me
Me
Me
8
7



G-155
Me
Me
Me
8
8



G-156
Me
Me
Me
8
9



G-157
Me
Me
Me
9
6



G-158
Me
Me
Me
9
7



G-159
Me
Me
Me
9
8



G-160
Me
Me
Me
9
9



G-161 G-162 G-163 G-164 G-165 G-166 G-167 G-168 G-169 G-170
Me Me Me Me Me Me Me Me Me Me
H H H H H H H H H H
H H H H H H H H H H
6 6 6 6 7 7 7 7 8 8
6 7 8 9 6 7 8 9 6 7


embedded image




G-171
Me
H
H
8
8



G-172
Me
H
H
8
9



G-173
Me
H
H
9
6



G-174
Me
H
H
9
7



G-175
Me
H
H
9
8



G-176
Me
H
H
9
9



G-177
H
H
Me
6
6



G-178
H
H
Me
6
7



G-179
H
H
Me
6
8



G-180
H
H
Me
6
9



G-181
H
H
Me
7
6



G-182
H
H
Me
7
7



G-183
H
H
Me
7
8



G-184
H
H
Me
7
9



G-185
H
H
Me
8
6



G-186
H
H
Me
8
7



G-187
H
H
Me
8
8



G-188
H
H
Me
8
9



G-189
H
H
Me
9
6



G-190
H
H
Me
9
7



G-191
H
H
Me
9
8



G-192
H
H
Me
9
9



G-193
Me
Me
H
6
6



G-194
Me
Me
H
6
7



G-195
Me
Me
H
6
8



G-196
Me
Me
H
6
9



G-197
Me
Me
H
7
6



G-198
Me
Me
H
7
7



G-199
Me
Me
H
7
8



G-200
Me
Me
H
7
9



G-201
Me
Me
H
8
6



G-202
Me
Me
H
8
7



G-203
Me
Me
H
8
8



G-204
Me
Me
H
8
9



G-205
Me
Me
H
9
6



G-206
Me
Me
H
9
7



G-207
Me
Me
H
9
8



G-208
Me
Me
H
9
9



G-209
H
Me
Me
6
6



G-210
H
Me
Me
6
7



G-211
H
Me
Me
6
8



G-212
H
Me
Me
6
9



G-213
H
Me
Me
7
6



G-214
H
Me
Me
7
7



G-215
H
Me
Me
7
8



G-216
H
Me
Me
7
9



G-217
H
Me
Me
8
6



G-218
H
Me
Me
8
7



G-219
H
Me
Me
8
8



G-220
H
Me
Me
8
9






















TABLE 31





Com-








pound








No.
Ra
Rb
Rc
n
m
W







G-221 G-222 G-223 G-224 G-225 G-226
H H H H Me Me
Me Me Me Me Me Me
Me Me Me Me Me Me
9 9 9 9 6 6
6 7 8 9 6 7


embedded image




G-227
Me
Me
Me
6
8



G-228
Me
Me
Me
6
9



G-229
Me
Me
Me
7
6



G-230
Me
Me
Me
7
7



G-231 G-232 G-233 G-234 G-235
Me Me Me Me Me
Me Me Me Me Me
Me Me Me Me Me
7 7 8 8 8
8 9 6 7 8



G-236
Me
Me
Me
8
9



G-237
Me
Me
Me
9
6



G-238
Me
Me
Me
9
7



G-239
Me
Me
Me
9
8



G-240
Me
Me
Me
9
9











embedded image













TABLE 32





Com-






pound






No.
Ra
n
m
W







H-1  H-2  H-3  H-4  H-5 
H H H H H
6 6 6 6 7
6 7 8 9 6


embedded image




H-6 
H
7
7



H-7 
H
7
8



H-8 
H
7
9



H-9 
H
8
6



H-10
H
8
7



H-11
H
8
8



H-12
H
8
9



H-13
H
9
6



H-14
H
9
7



H-15
H
9
8



H-16
H
9
9



H-17
Me
6
6



H-18
Me
6
7



H-19
Me
6
8



H-20
Me
6
9



H-21
Me
7
6



H-22
Me
7
7



H-23
Me
7
8



H-24
Me
7
9



H-25
Me
8
6



H-26
Me
8
7



H-27
Me
8
8



H-28
Me
8
9



H-29
Me
9
6



H-30
Me
9
7



H-31
Me
9
8



H-32
Me
9
9



H-33 H-34 H-35 H-36 H-37
H H H H H
6 6 6 6 7
6 7 8 9 6


embedded image




H-38
H
7
7



H-39
H
7
8



H-40
H
7
9



H-41
H
8
6



H-42
H
8
7



H-43
H
8
8



H-44
H
8
9



H-45
H
9
6



H-46
H
9
7



H-47
H
9
8



H-48
H
9
9



H-49
Me
6
6



H-50
Me
6
7



H-51
Me
6
8



H-52
Me
6
9



H-53
Me
7
6



H-54
Me
7
7



H-55
Me
7
8



H-56
Me
7
9



H-57
Me
8
6



H-58
Me
8
7



H-59
Me
8
8



H-60
Me
8
9



H-61
Me
9
6



H-62
Me
9
7



H-63
Me
9
8



H-64
Me
9
9



H-65 H-66 H-67 H-68 H-69 H-70
H H H H H H
6 6 6 6 7 7
6 7 8 9 6 7


embedded image




H-71
H
7
8



H-72
H
7
9



H-73
H
8
6



H-74
H
8
7



H-75
H
8
8



H-76
H
8
9



H-77
H
9
6



H-78
H
9
7



H-79
H
9
8



H-80
H
9
9



H-81
Me
6
6



H-82
Me
6
7



H-83
Me
6
8



H-84
Me
6
9



H-85
Me
7
6



H-86
Me
7
7



H-87
Me
7
8



H-88
Me
7
9



H-89
Me
8
6



H-90
Me
8
7



H-91
Me
8
8



H-92
Me
8
9



H-93
Me
9
6



H-94
Me
9
7



H-95
Me
9
8



H-96
Me
9
9











embedded image















TABLE 33





Com-








pound








No.
Ra
Rb
Rc
n
m
W







I-1  I-2  I-3  I-4  I-5 
Me Me Me Me Me
H H H H H
H H H H H
6 6 6 6 7
6 7 8 9 6


embedded image




I-6 
Me
H
H
7
7



I-7 
Me
H
H
7
8



I-8 
Me
H
H
7
9



I-9 
Me
H
H
8
6



I-10
Me
H
H
8
7



I-11
Me
H
H
8
8



I-12
Me
H
H
8
9



I-13
Me
H
H
9
6



I-14
Me
H
H
9
7



I-15
Me
H
H
9
8



I-16
Me
H
H
9
9



I-17
H
H
Me
6
6



I-18
H
H
Me
6
7



I-19
H
H
Me
6
8



I-20
H
H
Me
6
9



I-21
H
H
Me
7
6



I-22
H
H
Me
7
7



I-23
H
H
Me
7
8



I-24
H
H
Me
7
9



I-25
H
H
Me
8
6



I-26
H
H
Me
8
7



I-27
H
H
Me
8
8



I-28
H
H
Me
8
9



I-29
H
H
Me
9
6



I-30
H
H
Me
9
7



I-31
H
H
Me
9
8



I-32
H
H
Me
9
9



I-33
Me
Me
H
6
6



I-34
Me
Me
H
6
7



I-35
Me
Me
H
6
8



I-36
Me
Me
H
6
9



I-37
Me
Me
H
7
6



I-38
Me
Me
H
7
7



I-39
Me
Me
H
7
8



I-40
Me
Me
H
7
9



I-41
Me
Me
H
8
6



I-42
Me
Me
H
8
7



I-43
Me
Me
H
8
8



I-44
Me
Me
H
8
9



I-45
Me
Me
H
9
6



I-46
Me
Me
H
9
7



I-47
Me
Me
H
9
8



I-48
Me
Me
H
9
9



I-49
H
Me
Me
6
6



I-50
H
Me
Me
6
7



I-51
H
Me
Me
6
8



I-52
H
Me
Me
6
9



I-53
H
Me
Me
7
6



I-54
H
Me
Me
7
7



I-55
H
Me
Me
7
8



I-56 I-57 I-58 I-59
H H H H
Me Me Me Me
Me Me Me Me
7 8 8 8
9 6 7 8



I-60
H
Me
Me
8
9



I-61
H
Me
Me
9
6



I-62
H
Me
Me
9
7



I-63
H
Me
Me
9
8



I-64
H
Me
Me
9
9



I-65
Me
Me
Me
6
6



I-66
Me
Me
Me
6
7



I-67
Me
Me
Me
6
8



I-68
Me
Me
Me
6
9



I-69
Me
Me
Me
7
6



I-70
Me
Me
Me
7
7



I-71
Me
Me
Me
7
8



I-72
Me
Me
Me
7
9



I-73
Me
Me
Me
8
6



I-74
Me
Me
Me
8
7



I-75
Me
Me
Me
8
8



I-76
Me
Me
Me
8
9



I-77
Me
Me
Me
9
6



I-78
Me
Me
Me
9
7



I-79
Me
Me
Me
9
8



I-80
Me
Me
Me
9
9



I-81 I-82 I-83 I-84 I-85
Me Me Me Me Me
H H H H H
H H H H H
6 6 6 6 7
6 7 8 9 6


embedded image




I-86
Me
H
H
7
7



I-87
Me
H
H
7
8



I-88
Me
H
H
7
9



I-89
Me
H
H
8
6



I-90
Me
H
H
8
7



I-91
Me
H
H
8
8



I-92
Me
H
H
8
9



I-93
Me
H
H
9
6



I-94
Me
H
H
9
7



I-95
Me
H
H
9
8



I-96
Me
H
H
9
9



I-97
H
H
Me
6
6



I-98
H
H
Me
6
7



I-99
H
H
Me
6
8



 I-100
H
H
Me
6
9



 I-101
H
H
Me
7
6



 I-102
H
H
Me
7
7



 I-103
H
H
Me
7
8



 I-104
H
H
Me
7
9



 I-105
H
H
Me
8
6



 I-106
H
H
Me
8
7



 I-107
H
H
Me
8
8



 I-108
H
H
Me
8
9



 I-109
H
H
Me
9
6



 I-110
H
H
Me
9
7






















TABLE 34





Com-








pound








No.
Ra
Rb
Rc
n
m
W







I-111 I-112 I-113 I-114 I-115
H H Me Me Me
H H Me Me Me
Me Me H H H
9 9 6 6 6
8 9 6 7 8


embedded image




I-116
Me
Me
H
6
9



I-117
Me
Me
H
7
6



I-118
Me
Me
H
7
7



I-119
Me
Me
H
7
8



I-120
Me
Me
H
7
9



I-121
Me
Me
H
8
6



I-122
Me
Me
H
8
7



I-123
Me
Me
H
8
8



I-124
Me
Me
H
8
9



I-125
Me
Me
H
9
6



I-126
Me
Me
H
9
7



I-127
Me
Me
H
9
8



I-128
Me
Me
H
9
9



I-129
H
Me
Me
6
6



I-130
H
Me
Me
6
7



I-131
H
Me
Me
6
8



I-132
H
Me
Me
6
9



I-133
H
Me
Me
7
6



I-134
H
Me
Me
7
7



I-135
H
Me
Me
7
8



I-136
H
Me
Me
7
9



I-137
H
Me
Me
8
6



I-138
H
Me
Me
8
7



I-139
H
Me
Me
8
8



I-140
H
Me
Me
8
9



I-141
H
Me
Me
9
6



I-142
H
Me
Me
9
7



I-143
H
Me
Me
9
8



I-144
H
Me
Me
9
9



I-145
Me
Me
Me
6
6



I-146
Me
Me
Me
6
7



I-147
Me
Me
Me
6
8



I-148
Me
Me
Me
6
9



I-149
Me
Me
Me
7
6



I-150
Me
Me
Me
7
7



I-151
Me
Me
Me
7
8



I-152
Me
Me
Me
7
9



I-153
Me
Me
Me
8
6



I-154
Me
Me
Me
8
7



I-155
Me
Me
Me
8
8



I-156
Me
Me
Me
8
9



I-157
Me
Me
Me
9
6



I-158
Me
Me
Me
9
7



I-159
Me
Me
Me
9
8



I-160
Me
Me
Me
9
9



I-161 I-162 I-163 I-164 I-165 I-166 I-167 I-168 I-169 I-170
Me Me Me Me Me Me Me Me Me Me
H H H H H H H H H H
H H H H H H H H H H
6 6 6 6 7 7 7 7 8 8
6 7 8 9 6 7 8 9 6 7


embedded image




I-171
Me
H
H
8
8



I-172
Me
H
H
8
9



I-173
Me
H
H
9
6



I-174
Me
H
H
9
7



I-175
Me
H
H
9
8



I-176
Me
H
H
9
9



I-177
H
H
Me
6
6



I-178
H
H
Me
6
7



I-179
H
H
Me
6
8



I-180
H
H
Me
6
9



I-181
H
H
Me
7
6



I-182
H
H
Me
7
7



I-183
H
H
Me
7
8



I-184
H
H
Me
7
9



I-185
H
H
Me
8
6



I-186
H
H
Me
8
7



I-187
H
H
Me
8
8



I-188
H
H
Me
8
9



I-189
H
H
Me
9
6



I-190
H
H
Me
9
7



I-191
H
H
Me
9
8



I-192
H
H
Me
9
9



I-193
Me
Me
H
6
6



I-194
Me
Me
H
6
7



I-195
Me
Me
H
6
8



I-196
Me
Me
H
6
9



I-197
Me
Me
H
7
6



I-198
Me
Me
H
7
7



I-199
Me
Me
H
7
8



I-200
Me
Me
H
7
9



I-201
Me
Me
H
8
6



I-202
Me
Me
H
8
7



I-203
Me
Me
H
8
8



I-204
Me
Me
H
8
9



I-205
Me
Me
H
9
6



I-206
Me
Me
H
9
7



I-207
Me
Me
H
9
8



I-208
Me
Me
H
9
9



I-209
H
Me
Me
6
6



I-210
H
Me
Me
6
7



I-211
H
Me
Me
6
8



I-212
H
Me
Me
6
9



I-213
H
Me
Me
7
6



I-214
H
Me
Me
7
7



I-215
H
Me
Me
7
8



I-216
H
Me
Me
7
9



I-217
H
Me
Me
8
6



I-218
H
Me
Me
8
7



I-219
H
Me
Me
8
8



I-220
H
Me
Me
8
9






















TABLE 35





Com-








pound








No.
Ra
Rb
Rc
n
m
W







I-221 I-222 I-223 I-224 I-225 I-226
H H H H Me Me
Me Me Me Me Me Me
Me Me Me Me Me Me
9 9 9 9 6 6
6 7 8 9 6 7


embedded image




I-227
Me
Me
Me
6
8



I-228
Me
Me
Me
6
9



I-229
Me
Me
Me
7
6



I-230
Me
Me
Me
7
7



I-231 I-232 I-233 I-234 I-235
Me Me Me Me Me
Me Me Me Me Me
Me Me Me Me Me
7 7 8 8 8
8 9 6 7 8



I-236
Me
Me
Me
8
9



I-237
Me
Me
Me
9
6



I-238
Me
Me
Me
9
7



I-239
Me
Me
Me
9
8



I-240
Me
Me
Me
9
9











embedded image

















TABLE 36





Compound










No.
G1
G2
Q1
Ra
Rb
Rc
n
m







J-1
CH
CH
—O—
Me
H
H
1
7


J-2
CH
CH
—O—
Me
H
H
1
8


J-3
CH
CH
—O—
Me
H
H
1
9


J-4
CH
CH
—O—
Me
H
H
2
7


J-5
CH
CH
—O—
Me
H
H
2
8


J-6
CH
CH
—O—
Me
H
H
2
9


J-7
CH
CH
—O—
Me
H
H
3
7


J-8
CH
CH
—O—
Me
H
H
3
8


J-9
CH
CH
—O—
Me
H
H
3
9


J-10
CH
CH
—O—
Me
H
H
4
7


J-11
CH
CH
—O—
Me
H
H
4
8


J-12
CH
CH
—O—
Me
H
H
4
9


J-13
CH
CH
—O—
Me
H
H
5
7


J-14
CH
CH
—O—
Me
H
H
5
8


J-15
CH
CH
—O—
Me
H
H
5
9


J-16
CH
CH
—O—
H
H
Me
1
7


J-17
CH
CH
—O—
H
H
Me
1
8


J-18
CH
CH
—O—
H
H
Me
1
9


J-19
CH
CH
—O—
H
H
Me
2
7


J-20
CH
CH
—O—
H
H
Me
2
8


J-21
CH
CH
—O—
H
H
Me
2
9


J-22
CH
CH
—O—
H
H
Me
3
7


J-23
CH
CH
—O—
H
H
Me
3
8


J-24
CH
CH
—O—
H
H
Me
3
9


J-25
CH
CH
—O—
H
H
Me
4
7


J-26
CH
CH
—O—
H
H
Me
4
8


J-27
CH
CH
—O—
H
H
Me
4
9


J-28
CH
CH
—O—
H
H
Me
5
7


J-29
CH
CH
—O—
H
H
Me
5
8


J-30
CH
CH
—O—
H
H
Me
5
9


J-31
CH
CH
—O—
Me
Me
H
1
7


J-32
CH
CH
—O—
Me
Me
H
1
8


J-33
CH
CH
—O—
Me
Me
H
1
9


J-34
CH
CH
—O—
Me
Me
H
2
7


J-35
CH
CH
—O—
Me
Me
H
2
8


J-36
CH
CH
—O—
Me
Me
H
2
9


J-37
CH
CH
—O—
Me
Me
H
3
7


J-38
CH
CH
—O—
Me
Me
H
3
8


J-39
CH
CH
—O—
Me
Me
H
3
9


J-40
CH
CH
—O—
Me
Me
H
4
7


J-41
CH
CH
—O—
Me
Me
H
4
8


J-42
CH
CH
—O—
Me
Me
H
4
9


J-43
CH
CH
—O—
Me
Me
H
5
7


J-44
CH
CH
—O—
Me
Me
H
5
8


J-45
CH
CH
—O—
Me
Me
H
5
9


J-46
CH
CH
—O—
H
Me
Me
1
7


J-47
CH
CH
—O—
H
Me
Me
1
8


J-48
CH
CH
—O—
H
Me
Me
1
9


J-49
CH
CH
—O—
H
Me
Me
2
7


J-50
CH
CH
—O—
H
Me
Me
2
8


J-51
CH
CH
—O—
H
Me
Me
2
9


J-52
CH
CH
—O—
H
Me
Me
3
7


J-53
CH
CH
—O—
H
Me
Me
3
8


J-54
CH
CH
—O—
H
Me
Me
3
9


J-55
CH
CH
—O—
H
Me
Me
4
7


J-56
CH
CH
—O—
H
Me
Me
4
8


J-57
CH
CH
—O—
H
Me
Me
4
9


J-58
CH
CH
—O—
H
Me
Me
5
7


J-59
CH
CH
—O—
H
Me
Me
5
8


J-60
CH
CH
—O—
H
Me
Me
5
9


J-61
CH
CH
—CH2O—
Me
H
H
1
7


J-62
CH
CH
—CH2O—
Me
H
H
1
8


J-63
CH
CH
—CH2O—
Me
H
H
1
9


J-64
CH
CH
—CH2O—
Me
H
H
2
7


J-65
CH
CH
—CH2O—
Me
H
H
2
8


J-66
CH
CH
—CH2O—
Me
H
H
2
9


J-67
CH
CH
—CH2O—
Me
H
H
3
7


J-68
CH
CH
—CH2O—
Me
H
H
3
8


J-69
CH
CH
—CH2O—
Me
H
H
3
9


J-70
CH
CH
—CH2O—
Me
H
H
4
7


J-71
CH
CH
—CH2O—
Me
H
H
4
8


J-72
CH
CH
—CH2O—
Me
H
H
4
9


J-73
CH
CH
—CH2O—
Me
H
H
5
7


J-74
CH
CH
—CH2O—
Me
H
H
5
8


J-75
CH
CH
—CH2O—
Me
H
H
5
9


J-76
CH
CH
—CH2O—
H
H
Me
1
7


J-77
CH
CH
—CH2O—
H
H
Me
1
8


J-78
CH
CH
—CH2O—
H
H
Me
1
9


J-79
CH
CH
—CH2O—
H
H
Me
2
7


J-80
CH
CH
—CH2O—
H
H
Me
2
8


J-81
CH
CH
—CH2O—
H
H
Me
2
9


J-82
CH
CH
—CH2O—
H
H
Me
3
7


J-83
CH
CH
—CH2O—
H
H
Me
3
8


J-84
CH
CH
—CH2O—
H
H
Me
3
9


J-85
CH
CH
—CH2O—
H
H
Me
4
7


J-86
CH
CH
—CH2O—
H
H
Me
4
8


J-87
CH
CH
—CH2O—
H
H
Me
4
9


J-88
CH
CH
—CH2O—
H
H
Me
5
7


J-89
CH
CH
—CH2O—
H
H
Me
5
8


J-90
CH
CH
—CH2O—
H
H
Me
5
9


J-91
CH
CH
—CH2O—
Me
Me
H
1
7


J-92
CH
CH
—CH2O—
Me
Me
H
1
8


J-93
CH
CH
—CH2O—
Me
Me
H
1
9


J-94
CH
CH
—CH2O—
Me
Me
H
2
7


J-95
CH
CH
—CH2O—
Me
Me
H
2
8


J-96
CH
CH
—CH2O—
Me
Me
H
2
9


J-97
CH
CH
—CH2O—
Me
Me
H
3
7


J-98
CH
CH
—CH2O—
Me
Me
H
3
8


J-99
CH
CH
—CH2O—
Me
Me
H
3
9


J-100
CH
CH
—CH2O—
Me
Me
H
4
7


J-101
CH
CH
—CH2O—
Me
Me
H
4
8


J-102
CH
CH
—CH2O—
Me
Me
H
4
9


J-103
CH
CH
—CH2O—
Me
Me
H
5
7


J-104
CH
CH
—CH2O—
Me
Me
H
5
8


J-105
CH
CH
—CH2O—
Me
Me
H
5
9


J-106
CH
CH
—CH2O—
H
Me
Me
1
7


J-107
CH
CH
—CH2O—
H
Me
Me
1
8


J-108
CH
CH
—CH2O—
H
Me
Me
1
9


J-109
CH
CH
—CH2O—
H
Me
Me
2
7


J-110
CH
CH
—CH2O—
H
Me
Me
2
8
























TABLE 37





Compound










No.
G1
G2
Q1
Ra
Rb
Rc
n
m







J-111
CH
CH
—CH2O—
H
Me
Me
2
9


J-112
CH
CH
—CH2O—
H
Me
Me
3
7


J-113
CH
CH
—CH2O—
H
Me
Me
3
8


J-114
CH
CH
—CH2O—
H
Me
Me
3
9


J-115
CH
CH
—CH2O—
H
Me
Me
4
7


J-116
CH
CH
—CH2O—
H
Me
Me
4
8


J-117
CH
CH
—CH2O—
H
Me
Me
4
9


J-118
CH
CH
—CH2O—
H
Me
Me
5
7


J-119
CH
CH
—CH2O—
H
Me
Me
5
8


J-120
CH
CH
—CH2O—
H
Me
Me
5
9


J-121
CH
CH
singlebond
Me
H
H
1
7


J-122
CH
CH
singlebond
Me
H
H
1
8


J-123
CH
CH
singlebond
Me
H
H
1
9


J-124
CH
CH
singlebond
Me
H
H
2
7


J-125
CH
CH
singlebond
Me
H
H
2
8


J-126
CH
CH
singlebond
Me
H
H
2
9


J-127
CH
CH
singlebond
Me
H
H
3
7


J-128
CH
CH
singlebond
Me
H
H
3
8


J-129
CH
CH
singlebond
Me
H
H
3
9


J-130
CH
CH
singlebond
Me
H
H
4
7


J-131
CH
CH
singlebond
Me
H
H
4
8


J-132
CH
CH
singlebond
Me
H
H
4
9


J-133
CH
CH
singlebond
Me
H
H
5
7


J-134
CH
CH
singlebond
Me
H
H
5
8


J-135
CH
CH
singlebond
Me
H
H
5
9


J-136
CH
CH
singlebond
H
H
Me
1
7


J-137
CH
CH
singlebond
H
H
Me
1
8


J-138
CH
CH
singlebond
H
H
Me
1
9


J-139
CH
CH
singlebond
H
H
Me
2
7


J-140
CH
CH
singlebond
H
H
Me
2
8


J-141
CH
CH
singlebond
H
H
Me
2
9


J-142
CH
CH
singlebond
H
H
Me
3
7


J-143
CH
CH
singlebond
H
H
Me
3
8


J-144
CH
CH
singlebond
H
H
Me
3
9


J-145
CH
CH
singlebond
H
H
Me
4
7


J-146
CH
CH
singlebond
H
H
Me
4
8


J-147
CH
CH
singlebond
H
H
Me
4
9


J-148
CH
CH
singlebond
H
H
Me
5
7


J-149
CH
CH
singlebond
H
H
Me
5
8


J-150
CH
CH
singlebond
H
H
Me
5
9


J-151
CH
CH
singlebond
Me
Me
H
1
7


J-152
CH
CH
singlebond
Me
Me
H
1
8


J-153
CH
CH
singlebond
Me
Me
H
1
9


J-154
CH
CH
singlebond
Me
Me
H
2
7


J-155
CH
CH
singlebond
Me
Me
H
2
8


J-156
CH
CH
singlebond
Me
Me
H
2
9


J-157
CH
CH
singlebond
Me
Me
H
3
7


J-158
CH
CH
singlebond
Me
Me
H
3
8


J-159
CH
CH
singlebond
Me
Me
H
3
9


J-160
CH
CH
singlebond
Me
Me
H
4
7


J-161
CH
CH
singlebond
Me
Me
H
4
8


J-162
CH
CH
singlebond
Me
Me
H
4
9


J-163
CH
CH
singlebond
Me
Me
H
5
7


J-164
CH
CH
singlebond
Me
Me
H
5
8


J-165
CH
CH
singlebond
Me
Me
H
5
9


J-166
CH
CH
singlebond
H
Me
Me
1
7


J-167
CH
CH
singlebond
H
Me
Me
1
8


J-168
CH
CH
singlebond
H
Me
Me
1
9


J-169
CH
CH
singlebond
H
Me
Me
2
7


J-170
CH
CH
singlebond
H
Me
Me
2
8


J-171
CH
CH
singlebond
H
Me
Me
2
9


J-172
CH
CH
singlebond
H
Me
Me
3
7


J-173
CH
CH
singlebond
H
Me
Me
3
8


J-174
CH
CH
singlebond
H
Me
Me
3
9


J-175
CH
CH
singlebond
H
Me
Me
4
7


J-176
CH
CH
singlebond
H
Me
Me
4
8


J-177
CH
CH
singlebond
H
Me
Me
4
9


J-178
CH
CH
singlebond
H
Me
Me
5
7


J-179
CH
CH
singlebond
H
Me
Me
5
8


J-180
CH
CH
singlebond
H
Me
Me
5
9


J-181
N
CH
—O—
Me
H
H
1
7


J-182
N
CH
—O—
Me
H
H
1
8


J-183
N
CH
—O—
Me
H
H
1
9


J-184
N
CH
—O—
Me
H
H
2
7


J-185
N
CH
—O—
Me
H
H
2
8


J-186
N
CH
—O—
Me
H
H
2
9


J-187
N
CH
—O—
Me
H
H
3
7


J-188
N
CH
—O—
Me
H
H
3
8


J-189
N
CH
—O—
Me
H
H
3
9


J-190
N
CH
—O—
Me
H
H
4
7


J-191
N
CH
—O—
Me
H
H
4
8


J-192
N
CH
—O—
Me
H
H
4
9


J-193
N
CH
—O—
Me
H
H
5
7


J-194
N
CH
—O—
Me
H
H
5
8


J-195
N
CH
—O—
Me
H
H
5
9


J-196
N
CH
—O—
H
H
Me
1
7


J-197
N
CH
—O—
H
H
Me
1
8


J-198
N
CH
—O—
H
H
Me
1
9


J-199
N
CH
—O—
H
H
Me
2
7


J-200
N
CH
—O—
H
H
Me
2
8


J-201
N
CH
—O—
H
H
Me
2
9


J-202
N
CH
—O—
H
H
Me
3
7


J-203
N
CH
—O—
H
H
Me
3
8


J-204
N
CH
—O—
H
H
Me
3
9


J-205
N
CH
—O—
H
H
Me
4
7


J-206
N
CH
—O—
H
H
Me
4
8


J-207
N
CH
—O—
H
H
Me
4
9


J-208
N
CH
—O—
H
H
Me
5
7


J-209
N
CH
—O—
H
H
Me
5
8


J-210
N
CH
—O—
H
H
Me
5
9


J-211
N
CH
—O—
Me
Me
H
1
7


J-212
N
CH
—O—
Me
Me
H
1
8


J-213
N
CH
—O—
Me
Me
H
1
9


J-214
N
CH
—O—
Me
Me
H
2
7


J-215
N
CH
—O—
Me
Me
H
2
8


J-216
N
CH
—O—
Me
Me
H
2
9


J-217
N
CH
—O—
Me
Me
H
3
7


J-218
N
CH
—O—
Me
Me
H
3
8


J-219
N
CH
—O—
Me
Me
H
3
9


J-220
N
CH
—O—
Me
Me
H
4
7
























TABLE 38





Compound










No.
G1
G2
Q1
Ra
Rb
Rc
n
m







J-221
N
CH
—O—
Me
Me
H
4
8


J-222
N
CH
—O—
Me
Me
H
4
9


J-223
N
CH
—O—
Me
Me
H
5
7


J-224
N
CH
—O—
Me
Me
H
5
8


J-225
N
CH
—O—
Me
Me
H
5
9


J-226
N
CH
—O—
H
Me
Me
1
7


J-227
N
CH
—O—
H
Me
Me
1
8


J-228
N
CH
—O—
H
Me
Me
1
9


J-229
N
CH
—O—
H
Me
Me
2
7


J-230
N
CH
—O—
H
Me
Me
2
8


J-231
N
CH
—O—
H
Me
Me
2
9


J-232
N
CH
—O—
H
Me
Me
3
7


J-233
N
CH
—O—
H
Me
Me
3
8


J-234
N
CH
—O—
H
Me
Me
3
9


J-235
N
CH
—O—
H
Me
Me
4
7


J-236
N
CH
—O—
H
Me
Me
4
8


J-237
N
CH
—O—
H
Me
Me
4
9


J-238
N
CH
—O—
H
Me
Me
5
7


J-239
N
CH
—O—
H
Me
Me
5
8


J-240
N
CH
—O—
H
Me
Me
5
9


J-241
N
CH
—CH2O—
Me
H
H
1
7


J-242
N
CH
—CH2O—
Me
H
H
1
8


J-243
N
CH
—CH2O—
Me
H
H
1
9


J-244
N
CH
—CH2O—
Me
H
H
2
7


J-245
N
CH
—CH2O—
Me
H
H
2
8


J-246
N
CH
—CH2O—
Me
H
H
2
9


J-247
N
CH
—CH2O—
Me
H
H
3
7


J-248
N
CH
—CH2O—
Me
H
H
3
8


J-249
N
CH
—CH2O—
Me
H
H
3
9


J-250
N
CH
—CH2O—
Me
H
H
4
7


J-251
N
CH
—CH2O—
Me
H
H
4
8


J-252
N
CH
—CH2O—
Me
H
H
4
9


J-253
N
CH
—CH2O—
Me
H
H
5
7


J-254
N
CH
—CH2O—
Me
H
H
5
8


J-255
N
CH
—CH2O—
Me
H
H
5
9


J-256
N
CH
—CH2O—
H
H
Me
1
7


J-257
N
CH
—CH2O—
H
H
Me
1
8


J-258
N
CH
—CH2O—
H
H
Me
1
9


J-259
N
CH
—CH2O—
H
H
Me
2
7


J-260
N
CH
—CH2O—
H
H
Me
2
8


J-261
N
CH
—CH2O—
H
H
Me
2
9


J-262
N
CH
—CH2O—
H
H
Me
3
7


J-263
N
CH
—CH2O—
H
H
Me
3
8


J-264
N
CH
—CH2O—
H
H
Me
3
9


J-265
N
CH
—CH2O—
H
H
Me
4
7


J-266
N
CH
—CH2O—
H
H
Me
4
8


J-267
N
CH
—CH2O—
H
H
Me
4
9


J-268
N
CH
—CH2O—
H
H
Me
5
7


J-269
N
CH
—CH2O—
H
H
Me
5
8


J-270
N
CH
—CH2O—
H
H
Me
5
9


J-271
N
CH
—CH2O—
Me
Me
H
1
7


J-272
N
CH
—CH2O—
Me
Me
H
1
8


J-273
N
CH
—CH2O—
Me
Me
H
1
9


J-274
N
CH
—CH2O—
Me
Me
H
2
7


J-275
N
CH
—CH2O—
Me
Me
H
2
8


J-276
N
CH
—CH2O—
Me
Me
H
2
9


J-277
N
CH
—CH2O—
Me
Me
H
3
7


J-278
N
CH
—CH2O—
Me
Me
H
3
8


J-279
N
CH
—CH2O—
Me
Me
H
3
9


J-280
N
CH
—CH2O—
Me
Me
H
4
7


J-281
N
CH
—CH2O—
Me
Me
H
4
8


J-282
N
CH
—CH2O—
Me
Me
H
4
9


J-283
N
CH
—CH2O—
Me
Me
H
5
7


J-284
N
CH
—CH2O—
Me
Me
H
5
8


J-285
N
CH
—CH2O—
Me
Me
H
5
9


J-286
N
CH
—CH2O—
H
Me
Me
1
7


J-287
N
CH
—CH2O—
H
Me
Me
1
8


J-288
N
CH
—CH2O—
H
Me
Me
1
9


J-289
N
CH
—CH2O—
H
Me
Me
2
7


J-290
N
CH
—CH2O—
H
Me
Me
2
8


J-291
N
CH
—CH2O—
H
Me
Me
2
9


J-292
N
CH
—CH2O—
H
Me
Me
3
7


J-293
N
CH
—CH2O—
H
Me
Me
3
8


J-294
N
CH
—CH2O—
H
Me
Me
3
9


J-295
N
CH
—CH2O—
H
Me
Me
4
7


J-296
N
CH
—CH2O—
H
Me
Me
4
8


J-297
N
CH
—CH2O—
H
Me
Me
4
9


J-298
N
CH
—CH2O—
H
Me
Me
5
7


J-299
N
CH
—CH2O—
H
Me
Me
5
8


J-300
N
CH
—CH2O—
H
Me
Me
5
9


J-301
N
CH
singlebond
Me
H
H
1
7


J-302
N
CH
singlebond
Me
H
H
1
8


J-303
N
CH
singlebond
Me
H
H
1
9


J-304
N
CH
singlebond
Me
H
H
2
7


J-305
N
CH
singlebond
Me
H
H
2
8


J-306
N
CH
singlebond
Me
H
H
2
9


J-307
N
CH
singlebond
Me
H
H
3
7


J-308
N
CH
singlebond
Me
H
H
3
8


J-309
N
CH
singlebond
Me
H
H
3
9


J-310
N
CH
singlebond
Me
H
H
4
7


J-311
N
CH
singlebond
Me
H
H
4
8


J-312
N
CH
singlebond
Me
H
H
4
9


J-313
N
CH
singlebond
Me
H
H
5
7


J-314
N
CH
singlebond
Me
H
H
5
8


J-315
N
CH
singlebond
Me
H
H
5
9


J-316
N
CH
singlebond
H
H
Me
1
7


J-317
N
CH
singlebond
H
H
Me
1
8


J-318
N
CH
singlebond
H
H
Me
1
9


J-319
N
CH
singlebond
H
H
Me
2
7


J-320
N
CH
singlebond
H
H
Me
2
8


J-321
N
CH
singlebond
H
H
Me
2
9


J-322
N
CH
singlebond
H
H
Me
3
7


J-323
N
CH
singlebond
H
H
Me
3
8


J-324
N
CH
singlebond
H
H
Me
3
9


J-325
N
CH
singlebond
H
H
Me
4
7


J-326
N
CH
singlebond
H
H
Me
4
8


J-327
N
CH
singlebond
H
H
Me
4
9


J-328
N
CH
singlebond
H
H
Me
5
7


J-329
N
CH
singlebond
H
H
Me
5
8


J-330
N
CH
singlebond
H
H
Me
5
9
























TABLE 39





Compound










No.
G1
G2
Q1
Ra
Rb
Rc
n
m







J-331
N
CH
singlebond
Me
Me
H
1
7


J-332
N
CH
singlebond
Me
Me
H
1
8


J-333
N
CH
singlebond
Me
Me
H
1
9


J-334
N
CH
singlebond
Me
Me
H
2
7


J-335
N
CH
singlebond
Me
Me
H
2
8


J-336
N
CH
singlebond
Me
Me
H
2
9


J-337
N
CH
singlebond
Me
Me
H
3
7


J-338
N
CH
singlebond
Me
Me
H
3
8


J-339
N
CH
singlebond
Me
Me
H
3
9


J-340
N
CH
singlebond
Me
Me
H
4
7


J-341
N
CH
singlebond
Me
Me
H
4
8


J-342
N
CH
singlebond
Me
Me
H
4
9


J-343
N
CH
singlebond
Me
Me
H
5
7


J-344
N
CH
singlebond
Me
Me
H
5
8


J-345
N
CH
singlebond
Me
Me
H
5
9


J-346
N
CH
singlebond
H
Me
Me
1
7


J-347
N
CH
singlebond
H
Me
Me
1
8


J-348
N
CH
singlebond
H
Me
Me
1
9


J-349
N
CH
singlebond
H
Me
Me
2
7


J-350
N
CH
singlebond
H
Me
Me
2
8


J-351
N
CH
singlebond
H
Me
Me
2
9


J-352
N
CH
singlebond
H
Me
Me
3
7


J-353
N
CH
singlebond
H
Me
Me
3
8


J-354
N
CH
singlebond
H
Me
Me
3
9


J-355
N
CH
singlebond
H
Me
Me
4
7


J-356
N
CH
singlebond
H
Me
Me
4
8


J-357
N
CH
singlebond
H
Me
Me
4
9


J-358
N
CH
singlebond
H
Me
Me
5
7


J-359
N
CH
singlebond
H
Me
Me
5
8


J-360
N
CH
singlebond
H
Me
Me
5
9


J-361
CH
N
—O—
Me
H
H
1
7


J-362
CH
N
—O—
Me
H
H
1
8


J-363
CH
N
—O—
Me
H
H
1
9


J-364
CH
N
—O—
Me
H
H
2
7


J-365
CH
N
—O—
Me
H
H
2
8


J-366
CH
N
—O—
Me
H
H
2
9


J-367
CH
N
—O—
Me
H
H
3
7


J-368
CH
N
—O—
Me
H
H
3
8


J-369
CH
N
—O—
Me
H
H
3
9


J-370
CH
N
—O—
Me
H
H
4
7


J-371
CH
N
—O—
Me
H
H
4
8


J-372
CH
N
—O—
Me
H
H
4
9


J-373
CH
N
—O—
Me
H
H
5
7


J-374
CH
N
—O—
Me
H
H
5
8


J-375
CH
N
—O—
Me
H
H
5
9


J-376
CH
N
—O—
H
H
Me
1
7


J-377
CH
N
—O—
H
H
Me
1
8


J-378
CH
N
—O—
H
H
Me
1
9


J-379
CH
N
—O—
H
H
Me
2
7


J-380
CH
N
—O—
H
H
Me
2
8


J-381
CH
N
—O—
H
H
Me
2
9


J-382
CH
N
—O—
H
H
Me
3
7


J-383
CH
N
—O—
H
H
Me
3
8


J-384
CH
N
—O—
H
H
Me
3
9


J-385
CH
N
—O—
H
H
Me
4
7


J-386
CH
N
—O—
H
H
Me
4
8


J-387
CH
N
—O—
H
H
Me
4
9


J-388
CH
N
—O—
H
H
Me
5
7


J-389
CH
N
—O—
H
H
Me
5
8


J-390
CH
N
—O—
H
H
Me
5
9


J-391
CH
N
—O—
Me
Me
H
1
7


J-392
CH
N
—O—
Me
Me
H
1
8


J-393
CH
N
—O—
Me
Me
H
1
9


J-394
CH
N
—O—
Me
Me
H
2
7


J-395
CH
N
—O—
Me
Me
H
2
8


J-396
CH
N
—O—
Me
Me
H
2
9


J-397
CH
N
—O—
Me
Me
H
3
7


J-398
CH
N
—O—
Me
Me
H
3
8


J-399
CH
N
—O—
Me
Me
H
3
9


J-400
CH
N
—O—
Me
Me
H
4
7


J-401
CH
N
—O—
Me
Me
H
4
8


J-402
CH
N
—O—
Me
Me
H
4
9


J-403
CH
N
—O—
Me
Me
H
5
7


J-404
CH
N
—O—
Me
Me
H
5
8


J-405
CH
N
—O—
Me
Me
H
5
9


J-406
CH
N
—O—
H
Me
Me
1
7


J-407
CH
N
—O—
H
Me
Me
1
8


J-408
CH
N
—O—
H
Me
Me
1
9


J-409
CH
N
—O—
H
Me
Me
2
7


J-410
CH
N
—O—
H
Me
Me
2
8


J-411
CH
N
—O—
H
Me
Me
2
9


J-412
CH
N
—O—
H
Me
Me
3
7


J-413
CH
N
—O—
H
Me
Me
3
8


J-414
CH
N
—O—
H
Me
Me
3
9


J-415
CH
N
—O—
H
Me
Me
4
7


J-416
CH
N
—O—
H
Me
Me
4
8


J-417
CH
N
—O—
H
Me
Me
4
9


J-418
CH
N
—O—
H
Me
Me
5
7


J-419
CH
N
—O—
H
Me
Me
5
8


J-420
CH
N
—O—
H
Me
Me
5
9


J-421
CH
N
—CH2O—
Me
H
H
1
7


J-422
CH
N
—CH2O—
Me
H
H
1
8


J-423
CH
N
—CH2O—
Me
H
H
1
9


J-424
CH
N
—CH2O—
Me
H
H
2
7


J-425
CH
N
—CH2O—
Me
H
H
2
8


J-426
CH
N
—CH2O—
Me
H
H
2
9


J-427
CH
N
—CH2O—
Me
H
H
3
7


J-428
CH
N
—CH2O—
Me
H
H
3
8


J-429
CH
N
—CH2O—
Me
H
H
3
9


J-430
CH
N
—CH2O—
Me
H
H
4
7


J-431
CH
N
—CH2O—
Me
H
H
4
8


J-432
CH
N
—CH2O—
Me
H
H
4
9


J-433
CH
N
—CH2O—
Me
H
H
5
7


J-434
CH
N
—CH2O—
Me
H
H
5
8


J-435
CH
N
—CH2O—
Me
H
H
5
9


J-436
CH
N
—CH2O—
H
H
Me
1
7


J-437
CH
N
—CH2O—
H
H
Me
1
8


J-438
CH
N
—CH2O—
H
H
Me
1
9


J-439
CH
N
—CH2O—
H
H
Me
2
7


J-440
CH
N
—CH2O—
H
H
Me
2
8
























TABLE 40





Compound










No.
G1
G2
Q1
Ra
Rb
Rc
n
m







J-441
CH
N
—CH2O—
H
H
Me
2
9


J-442
CH
N
—CH2O—
H
H
Me
3
7


J-443
CH
N
—CH2O—
H
H
Me
3
8


J-444
CH
N
—CH2O—
H
H
Me
3
9


J-445
CH
N
—CH2O—
H
H
Me
4
7


J-446
CH
N
—CH2O—
H
H
Me
4
8


J-447
CH
N
—CH2O—
H
H
Me
4
9


J-448
CH
N
—CH2O—
H
H
Me
5
7


J-449
CH
N
—CH2O—
H
H
Me
5
8


J-450
CH
N
—CH2O—
H
H
Me
5
9


J-451
CH
N
—CH2O—
Me
Me
H
1
7


J-452
CH
N
—CH2O—
Me
Me
H
1
8


J-453
CH
N
—CH2O—
Me
Me
H
1
9


J-454
CH
N
—CH2O—
Me
Me
H
2
7


J-455
CH
N
—CH2O—
Me
Me
H
2
8


J-456
CH
N
—CH2O—
Me
Me
H
2
9


J-457
CH
N
—CH2O—
Me
Me
H
3
7


J-458
CH
N
—CH2O—
Me
Me
H
3
8


J-459
CH
N
—CH2O—
Me
Me
H
3
9


J-460
CH
N
—CH2O—
Me
Me
H
4
7


J-461
CH
N
—CH2O—
Me
Me
H
4
8


J-462
CH
N
—CH2O—
Me
Me
H
4
9


J-463
CH
N
—CH2O—
Me
Me
H
5
7


J-464
CH
N
—CH2O—
Me
Me
H
5
8


J-465
CH
N
—CH2O—
Me
Me
H
5
9


J-466
CH
N
—CH2O—
H
Me
Me
1
7


J-467
CH
N
—CH2O—
H
Me
Me
1
8


J-468
CH
N
—CH2O—
H
Me
Me
1
9


J-469
CH
N
—CH2O—
H
Me
Me
2
7


J-470
CH
N
—CH2O—
H
Me
Me
2
8


J-471
CH
N
—CH2O—
H
Me
Me
2
9


J-472
CH
N
—CH2O—
H
Me
Me
3
7


J-473
CH
N
—CH2O—
H
Me
Me
3
8


J-474
CH
N
—CH2O—
H
Me
Me
3
9


J-475
CH
N
—CH2O—
H
Me
Me
4
7


J-476
CH
N
—CH2O—
H
Me
Me
4
8


J-477
CH
N
—CH2O—
H
Me
Me
4
9


J-478
CH
N
—CH2O—
H
Me
Me
5
7


J-479
CH
N
—CH2O—
H
Me
Me
5
8


J-480
CH
N
—CH2O—
H
Me
Me
5
9


J-481
CH
N
singlebond
Me
H
H
1
7


J-482
CH
N
singlebond
Me
H
H
1
8


J-483
CH
N
singlebond
Me
H
H
1
9


J-484
CH
N
singlebond
Me
H
H
2
7


J-485
CH
N
singlebond
Me
H
H
2
8


J-486
CH
N
singlebond
Me
H
H
2
9


J-487
CH
N
singlebond
Me
H
H
3
7


J-488
CH
N
singlebond
Me
H
H
3
8


J-489
CH
N
singlebond
Me
H
H
3
9


J-490
CH
N
singlebond
Me
H
H
4
7


J-491
CH
N
singlebond
Me
H
H
4
8


J-492
CH
N
singlebond
Me
H
H
4
9


J-493
CH
N
singlebond
Me
H
H
5
7


J-494
CH
N
singlebond
Me
H
H
5
8


J-495
CH
N
singlebond
Me
H
H
5
9


J-496
CH
N
singlebond
H
H
Me
1
7


J-497
CH
N
singlebond
H
H
Me
1
8


J-498
CH
N
singlebond
H
H
Me
1
9


J-499
CH
N
singlebond
H
H
Me
2
7


J-500
CH
N
singlebond
H
H
Me
2
8


J-501
CH
N
singlebond
H
H
Me
2
9


J-502
CH
N
singlebond
H
H
Me
3
7


J-503
CH
N
singlebond
H
H
Me
3
8


J-504
CH
N
singlebond
H
H
Me
3
9


J-505
CH
N
singlebond
H
H
Me
4
7


J-506
CH
N
singlebond
H
H
Me
4
8


J-507
CH
N
singlebond
H
H
Me
4
9


J-508
CH
N
singlebond
H
H
Me
5
7


J-509
CH
N
singlebond
H
H
Me
5
8


J-510
CH
N
singlebond
H
H
Me
5
9


J-511
CH
N
singlebond
Me
Me
H
1
7


J-512
CH
N
singlebond
Me
Me
H
1
8


J-513
CH
N
singlebond
Me
Me
H
1
9


J-514
CH
N
singlebond
Me
Me
H
2
7


J-515
CH
N
singlebond
Me
Me
H
2
8


J-516
CH
N
singlebond
Me
Me
H
2
9


J-517
CH
N
singlebond
Me
Me
H
3
7


J-518
CH
N
singlebond
Me
Me
H
3
8


J-519
CH
N
singlebond
Me
Me
H
3
9


J-520
CH
N
singlebond
Me
Me
H
4
7


J-521
CH
N
singlebond
Me
Me
H
4
8


J-522
CH
N
singlebond
Me
Me
H
4
9


J-523
CH
N
singlebond
Me
Me
H
5
7


J-524
CH
N
singlebond
Me
Me
H
5
8


J-525
CH
N
singlebond
Me
Me
H
5
9


J-526
CH
N
singlebond
H
Me
Me
1
7


J-527
CH
N
singlebond
H
Me
Me
1
8


J-528
CH
N
singlebond
H
Me
Me
1
9


J-529
CH
N
singlebond
H
Me
Me
2
7


J-530
CH
N
singlebond
H
Me
Me
2
8


J-531
CH
N
singlebond
H
Me
Me
2
9


J-532
CH
N
singlebond
H
Me
Me
3
7


J-533
CH
N
singlebond
H
Me
Me
3
8


J-534
CH
N
singlebond
H
Me
Me
3
9


J-535
CH
N
singlebond
H
Me
Me
4
7


J-536
CH
N
singlebond
H
Me
Me
4
8


J-537
CH
N
singlebond
H
Me
Me
4
9


J-538
CH
N
singlebond
H
Me
Me
5
7


J-539
CH
N
singlebond
H
Me
Me
5
8


J-540
CH
N
singlebond
H
Me
Me
5
9











embedded image

















TABLE 41





Compound










No.
G1
G2
Q1
Ra
Rb
Rc
n
m







K-1
CH
CH
—O—
Me
H
H
1
7


K-2
CH
CH
—O—
Me
H
H
1
8


K-3
CH
CH
—O—
Me
H
H
1
9


K-4
CH
CH
—O—
Me
H
H
2
7


K-5
CH
CH
—O—
Me
H
H
2
8


K-6
CH
CH
—O—
Me
H
H
2
9


K-7
CH
CH
—O—
Me
H
H
3
7


K-8
CH
CH
—O—
Me
H
H
3
8


K-9
CH
CH
—O—
Me
H
H
3
9


K-10
CH
CH
—O—
Me
H
H
4
7


K-11
CH
CH
—O—
Me
H
H
4
8


K-12
CH
CH
—O—
Me
H
H
4
9


K-13
CH
CH
—O—
Me
H
H
5
7


K-14
CH
CH
—O—
Me
H
H
5
8


K-15
CH
CH
—O—
Me
H
H
5
9


K-16
CH
CH
—O—
H
H
Me
1
7


K-17
CH
CH
—O—
H
H
Me
1
8


K-18
CH
CH
—O—
H
H
Me
1
9


K-19
CH
CH
—O—
H
H
Me
2
7


K-20
CH
CH
—O—
H
H
Me
2
8


K-21
CH
CH
—O—
H
H
Me
2
9


K-22
CH
CH
—O—
H
H
Me
3
7


K-23
CH
CH
—O—
H
H
Me
3
8


K-24
CH
CH
—O—
H
H
Me
3
9


K-25
CH
CH
—O—
H
H
Me
4
7


K-26
CH
CH
—O—
H
H
Me
4
8


K-27
CH
CH
—O—
H
H
Me
4
9


K-28
CH
CH
—O—
H
H
Me
5
7


K-29
CH
CH
—O—
H
H
Me
5
8


K-30
CH
CH
—O—
H
H
Me
5
9


K-31
CH
CH
—O—
Me
Me
H
1
7


K-32
CH
CH
—O—
Me
Me
H
1
8


K-33
CH
CH
—O—
Me
Me
H
1
9


K-34
CH
CH
—O—
Me
Me
H
2
7


K-35
CH
CH
—O—
Me
Me
H
2
8


K-36
CH
CH
—O—
Me
Me
H
2
9


K-37
CH
CH
—O—
Me
Me
H
3
7


K-38
CH
CH
—O—
Me
Me
H
3
8


K-39
CH
CH
—O—
Me
Me
H
3
9


K-40
CH
CH
—O—
Me
Me
H
4
7


K-41
CH
CH
—O—
Me
Me
H
4
8


K-42
CH
CH
—O—
Me
Me
H
4
9


K-43
CH
CH
—O—
Me
Me
H
5
7


K-44
CH
CH
—O—
Me
Me
H
5
8


K-45
CH
CH
—O—
Me
Me
H
5
9


K-46
CH
CH
—O—
H
Me
Me
1
7


K-47
CH
CH
—O—
H
Me
Me
1
8


K-48
CH
CH
—O—
H
Me
Me
1
9


K-49
CH
CH
—O—
H
Me
Me
2
7


K-50
CH
CH
—O—
H
Me
Me
2
8


K-51
CH
CH
—O—
H
Me
Me
2
9


K-52
CH
CH
—O—
H
Me
Me
3
7


K-53
CH
CH
—O—
H
Me
Me
3
8


K-54
CH
CH
—O—
H
Me
Me
3
9


K-55
CH
CH
—O—
H
Me
Me
4
7


K-56
CH
CH
—O—
H
Me
Me
4
8


K-57
CH
CH
—O—
H
Me
Me
4
9


K-58
CH
CH
—O—
H
Me
Me
5
7


K-59
CH
CH
—O—
H
Me
Me
5
8


K-60
CH
CH
—O—
H
Me
Me
5
9


K-61
CH
CH
—CH2O—
Me
H
H
1
7


K-62
CH
CH
—CH2O—
Me
H
H
1
8


K-63
CH
CH
—CH2O—
Me
H
H
1
9


K-64
CH
CH
—CH2O—
Me
H
H
2
7


K-65
CH
CH
—CH2O—
Me
H
H
2
8


K-66
CH
CH
—CH2O—
Me
H
H
2
9


K-67
CH
CH
—CH2O—
Me
H
H
3
7


K-68
CH
CH
—CH2O—
Me
H
H
3
8


K-69
CH
CH
—CH2O—
Me
H
H
3
9


K-70
CH
CH
—CH2O—
Me
H
H
4
7


K-71
CH
CH
—CH2O—
Me
H
H
4
8


K-72
CH
CH
—CH2O—
Me
H
H
4
9


K-73
CH
CH
—CH2O—
Me
H
H
5
7


K-74
CH
CH
—CH2O—
Me
H
H
5
8


K-75
CH
CH
—CH2O—
Me
H
H
5
9


K-76
CH
CH
—CH2O—
H
H
Me
1
7


K-77
CH
CH
—CH2O—
H
H
Me
1
8


K-78
CH
CH
—CH2O—
H
H
Me
1
9


K-79
CH
CH
—CH2O—
H
H
Me
2
7


K-80
CH
CH
—CH2O—
H
H
Me
2
8


K-81
CH
CH
—CH2O—
H
H
Me
2
9


K-82
CH
CH
—CH2O—
H
H
Me
3
7


K-83
CH
CH
—CH2O—
H
H
Me
3
8


K-84
CH
CH
—CH2O—
H
H
Me
3
9


K-85
CH
CH
—CH2O—
H
H
Me
4
7


K-86
CH
CH
—CH2O—
H
H
Me
4
8


K-87
CH
CH
—CH2O—
H
H
Me
4
9


K-88
CH
CH
—CH2O—
H
H
Me
5
7


K-89
CH
CH
—CH2O—
H
H
Me
5
8


K-90
CH
CH
—CH2O—
H
H
Me
5
9


K-91
CH
CH
—CH2O—
Me
Me
H
1
7


K-92
CH
CH
—CH2O—
Me
Me
H
1
8


K-93
CH
CH
—CH2O—
Me
Me
H
1
9


K-94
CH
CH
—CH2O—
Me
Me
H
2
7


K-95
CH
CH
—CH2O—
Me
Me
H
2
8


K-96
CH
CH
—CH2O—
Me
Me
H
2
9


K-97
CH
CH
—CH2O—
Me
Me
H
3
7


K-98
CH
CH
—CH2O—
Me
Me
H
3
8


K-99
CH
CH
—CH2O—
Me
Me
H
3
9


K-100
CH
CH
—CH2O—
Me
Me
H
4
7


K-101
CH
CH
—CH2O—
Me
Me
H
4
8


K-102
CH
CH
—CH2O—
Me
Me
H
4
9


K-103
CH
CH
—CH2O—
Me
Me
H
5
7


K-104
CH
CH
—CH2O—
Me
Me
H
5
8


K-105
CH
CH
—CH2O—
Me
Me
H
5
9


K-106
CH
CH
—CH2O—
H
Me
Me
1
7


K-107
CH
CH
—CH2O—
H
Me
Me
1
8


K-108
CH
CH
—CH2O—
H
Me
Me
1
9


K-109
CH
CH
—CH2O—
H
Me
Me
2
7


K-110
CH
CH
—CH2O—
H
Me
Me
2
8
























TABLE 42





Compound










No.
G1
G2
Q1
Ra
Rb
Rc
n
m







K-111
CH
CH
—CH2O—
H
Me
Me
2
9


K-112
CH
CH
—CH2O—
H
Me
Me
3
7


K-113
CH
CH
—CH2O—
H
Me
Me
3
8


K-114
CH
CH
—CH2O—
H
Me
Me
3
9


K-115
CH
CH
—CH2O—
H
Me
Me
4
7


K-116
CH
CH
—CH2O—
H
Me
Me
4
8


K-117
CH
CH
—CH2O—
H
Me
Me
4
9


K-118
CH
CH
—CH2O—
H
Me
Me
5
7


K-119
CH
CH
—CH2O—
H
Me
Me
5
8


K-120
CH
CH
—CH2O—
H
Me
Me
5
9


K-121
CH
CH
singlebond
Me
H
H
1
7


K-122
CH
CH
singlebond
Me
H
H
1
8


K-123
CH
CH
singlebond
Me
H
H
1
9


K-124
CH
CH
singlebond
Me
H
H
2
7


K-125
CH
CH
singlebond
Me
H
H
2
8


K-126
CH
CH
singlebond
Me
H
H
2
9


K-127
CH
CH
singlebond
Me
H
H
3
7


K-128
CH
CH
singlebond
Me
H
H
3
8


K-129
CH
CH
singlebond
Me
H
H
3
9


K-130
CH
CH
singlebond
Me
H
H
4
7


K-131
CH
CH
singlebond
Me
H
H
4
8


K-132
CH
CH
singlebond
Me
H
H
4
9


K-133
CH
CH
singlebond
Me
H
H
5
7


K-134
CH
CH
singlebond
Me
H
H
5
8


K-135
CH
CH
singlebond
Me
H
H
5
9


K-136
CH
CH
singlebond
H
H
Me
1
7


K-137
CH
CH
singlebond
H
H
Me
1
8


K-138
CH
CH
singlebond
H
H
Me
1
9


K-139
CH
CH
singlebond
H
H
Me
2
7


K-140
CH
CH
singlebond
H
H
Me
2
8


K-141
CH
CH
singlebond
H
H
Me
2
9


K-142
CH
CH
singlebond
H
H
Me
3
7


K-143
CH
CH
singlebond
H
H
Me
3
8


K-144
CH
CH
singlebond
H
H
Me
3
9


K-145
CH
CH
singlebond
H
H
Me
4
7


K-146
CH
CH
singlebond
H
H
Me
4
8


K-147
CH
CH
singlebond
H
H
Me
4
9


K-148
CH
CH
singlebond
H
H
Me
5
7


K-149
CH
CH
singlebond
H
H
Me
5
8


K-150
CH
CH
singlebond
H
H
Me
5
9


K-151
CH
CH
singlebond
Me
Me
H
1
7


K-152
CH
CH
singlebond
Me
Me
H
1
8


K-153
CH
CH
singlebond
Me
Me
H
1
9


K-154
CH
CH
singlebond
Me
Me
H
2
7


K-155
CH
CH
singlebond
Me
Me
H
2
8


K-156
CH
CH
singlebond
Me
Me
H
2
9


K-157
CH
CH
singlebond
Me
Me
H
3
7


K-158
CH
CH
singlebond
Me
Me
H
3
8


K-159
CH
CH
singlebond
Me
Me
H
3
9


K-160
CH
CH
singlebond
Me
Me
H
4
7


K-161
CH
CH
singlebond
Me
Me
H
4
8


K-162
CH
CH
singlebond
Me
Me
H
4
9


K-163
CH
CH
singlebond
Me
Me
H
5
7


K-164
CH
CH
singlebond
Me
Me
H
5
8


K-165
CH
CH
singlebond
Me
Me
H
5
9


K-166
CH
CH
singlebond
H
Me
Me
1
7


K-167
CH
CH
singlebond
H
Me
Me
1
8


K-168
CH
CH
singlebond
H
Me
Me
1
9


K-169
CH
CH
singlebond
H
Me
Me
2
7


K-170
CH
CH
singlebond
H
Me
Me
2
8


K-171
CH
CH
singlebond
H
Me
Me
2
9


K-172
CH
CH
singlebond
H
Me
Me
3
7


K-173
CH
CH
singlebond
H
Me
Me
3
8


K-174
CH
CH
singlebond
H
Me
Me
3
9


K-175
CH
CH
singlebond
H
Me
Me
4
7


K-176
CH
CH
singlebond
H
Me
Me
4
8


K-177
CH
CH
singlebond
H
Me
Me
4
9


K-178
CH
CH
singlebond
H
Me
Me
5
7


K-179
CH
CH
singlebond
H
Me
Me
5
8


K-180
CH
CH
singlebond
H
Me
Me
5
9


K-181
N
CH
—O—
Me
H
H
1
7


K-182
N
CH
—O—
Me
H
H
1
8


K-183
N
CH
—O—
Me
H
H
1
9


K-184
N
CH
—O—
Me
H
H
2
7


K-185
N
CH
—O—
Me
H
H
2
8


K-186
N
CH
—O—
Me
H
H
2
9


K-187
N
CH
—O—
Me
H
H
3
7


K-188
N
CH
—O—
Me
H
H
3
8


K-189
N
CH
—O—
Me
H
H
3
9


K-190
N
CH
—O—
Me
H
H
4
7


K-191
N
CH
—O—
Me
H
H
4
8


K-192
N
CH
—O—
Me
H
H
4
9


K-193
N
CH
—O—
Me
H
H
5
7


K-194
N
CH
—O—
Me
H
H
5
8


K-195
N
CH
—O—
Me
H
H
5
9


K-196
N
CH
—O—
H
H
Me
1
7


K-197
N
CH
—O—
H
H
Me
1
8


K-198
N
CH
—O—
H
H
Me
1
9


K-199
N
CH
—O—
H
H
Me
2
7


K-200
N
CH
—O—
H
H
Me
2
8


K-201
N
CH
—O—
H
H
Me
2
9


K-202
N
CH
—O—
H
H
Me
3
7


K-203
N
CH
—O—
H
H
Me
3
8


K-204
N
CH
—O—
H
H
Me
3
9


K-205
N
CH
—O—
H
H
Me
4
7


K-206
N
CH
—O—
H
H
Me
4
8


K-207
N
CH
—O—
H
H
Me
4
9


K-208
N
CH
—O—
H
H
Me
5
7


K-209
N
CH
—O—
H
H
Me
5
8


K-210
N
CH
—O—
H
H
Me
5
9


K-211
N
CH
—O—
Me
Me
H
1
7


K-212
N
CH
—O—
Me
Me
H
1
8


K-213
N
CH
—O—
Me
Me
H
1
9


K-214
N
CH
—O—
Me
Me
H
2
7


K-215
N
CH
—O—
Me
Me
H
2
8


K-216
N
CH
—O—
Me
Me
H
2
9


K-217
N
CH
—O—
Me
Me
H
3
7


K-218
N
CH
—O—
Me
Me
H
3
8


K-219
N
CH
—O—
Me
Me
H
3
9


K-220
N
CH
—O—
Me
Me
H
4
7
























TABLE 43





Compound










No.
G1
G2
Q1
Ra
Rb
Rc
n
m







K-221
N
CH
—O—
Me
Me
H
4
8


K-222
N
CH
—O—
Me
Me
H
4
9


K-223
N
CH
—O—
Me
Me
H
5
7


K-224
N
CH
—O—
Me
Me
H
5
8


K-225
N
CH
—O—
Me
Me
H
5
9


K-226
N
CH
—O—
H
Me
Me
1
7


K-227
N
CH
—O—
H
Me
Me
1
8


K-228
N
CH
—O—
H
Me
Me
1
9


K-229
N
CH
—O—
H
Me
Me
2
7


K-230
N
CH
—O—
H
Me
Me
2
8


K-231
N
CH
—O—
H
Me
Me
2
9


K-232
N
CH
—O—
H
Me
Me
3
7


K-233
N
CH
—O—
H
Me
Me
3
8


K-234
N
CH
—O—
H
Me
Me
3
9


K-235
N
CH
—O—
H
Me
Me
4
7


K-236
N
CH
—O—
H
Me
Me
4
8


K-237
N
CH
—O—
H
Me
Me
4
9


K-238
N
CH
—O—
H
Me
Me
5
7


K-239
N
CH
—O—
H
Me
Me
5
8


K-240
N
CH
—O—
H
Me
Me
5
9


K-241
N
CH
—CH2O—
Me
H
H
1
7


K-242
N
CH
—CH2O—
Me
H
H
1
8


K-243
N
CH
—CH2O—
Me
H
H
1
9


K-244
N
CH
—CH2O—
Me
H
H
2
7


K-245
N
CH
—CH2O—
Me
H
H
2
8


K-246
N
CH
—CH2O—
Me
H
H
2
9


K-247
N
CH
—CH2O—
Me
H
H
3
7


K-248
N
CH
—CH2O—
Me
H
H
3
8


K-249
N
CH
—CH2O—
Me
H
H
3
9


K-250
N
CH
—CH2O—
Me
H
H
4
7


K-251
N
CH
—CH2O—
Me
H
H
4
8


K-252
N
CH
—CH2O—
Me
H
H
4
9


K-253
N
CH
—CH2O—
Me
H
H
5
7


K-254
N
CH
—CH2O—
Me
H
H
5
8


K-255
N
CH
—CH2O—
Me
H
H
5
9


K-256
N
CH
—CH2O—
H
H
Me
1
7


K-257
N
CH
—CH2O—
H
H
Me
1
8


K-258
N
CH
—CH2O—
H
H
Me
1
9


K-259
N
CH
—CH2O—
H
H
Me
2
7


K-260
N
CH
—CH2O—
H
H
Me
2
8


K-261
N
CH
—CH2O—
H
H
Me
2
9


K-262
N
CH
—CH2O—
H
H
Me
3
7


K-263
N
CH
—CH2O—
H
H
Me
3
8


K-264
N
CH
—CH2O—
H
H
Me
3
9


K-265
N
CH
—CH2O—
H
H
Me
4
7


K-266
N
CH
—CH2O—
H
H
Me
4
8


K-267
N
CH
—CH2O—
H
H
Me
4
9


K-268
N
CH
—CH2O—
H
H
Me
5
7


K-269
N
CH
—CH2O—
H
H
Me
5
8


K-270
N
CH
—CH2O—
H
H
Me
5
9


K-271
N
CH
—CH2O—
Me
Me
H
1
7


K-272
N
CH
—CH2O—
Me
Me
H
1
8


K-273
N
CH
—CH2O—
Me
Me
H
1
9


K-274
N
CH
—CH2O—
Me
Me
H
2
7


K-275
N
CH
—CH2O—
Me
Me
H
2
8


K-276
N
CH
—CH2O—
Me
Me
H
2
9


K-277
N
CH
—CH2O—
Me
Me
H
3
7


K-278
N
CH
—CH2O—
Me
Me
H
3
8


K-279
N
CH
—CH2O—
Me
Me
H
3
9


K-280
N
CH
—CH2O—
Me
Me
H
4
7


K-281
N
CH
—CH2O—
Me
Me
H
4
8


K-282
N
CH
—CH2O—
Me
Me
H
4
9


K-283
N
CH
—CH2O—
Me
Me
H
5
7


K-284
N
CH
—CH2O—
Me
Me
H
5
8


K-285
N
CH
—CH2O—
Me
Me
H
5
9


K-286
N
CH
—CH2O—
H
Me
Me
1
7


K-287
N
CH
—CH2O—
H
Me
Me
1
8


K-288
N
CH
—CH2O—
H
Me
Me
1
9


K-289
N
CH
—CH2O—
H
Me
Me
2
7


K-290
N
CH
—CH2O—
H
Me
Me
2
8


K-291
N
CH
—CH2O—
H
Me
Me
2
9


K-292
N
CH
—CH2O—
H
Me
Me
3
7


K-293
N
CH
—CH2O—
H
Me
Me
3
8


K-294
N
CH
—CH2O—
H
Me
Me
3
9


K-295
N
CH
—CH2O—
H
Me
Me
4
7


K-296
N
CH
—CH2O—
H
Me
Me
4
8


K-297
N
CH
—CH2O—
H
Me
Me
4
9


K-298
N
CH
—CH2O—
H
Me
Me
5
7


K-299
N
CH
—CH2O—
H
Me
Me
5
8


K-300
N
CH
—CH2O—
H
Me
Me
5
9


K-301
N
CH
singlebond
Me
H
H
1
7


K-302
N
CH
singlebond
Me
H
H
1
8


K-303
N
CH
singlebond
Me
H
H
1
9


K-304
N
CH
singlebond
Me
H
H
2
7


K-305
N
CH
singlebond
Me
H
H
2
8


K-306
N
CH
singlebond
Me
H
H
2
9


K-307
N
CH
singlebond
Me
H
H
3
7


K-308
N
CH
singlebond
Me
H
H
3
8


K-309
N
CH
singlebond
Me
H
H
3
9


K-310
N
CH
singlebond
Me
H
H
4
7


K-311
N
CH
singlebond
Me
H
H
4
8


K-312
N
CH
singlebond
Me
H
H
4
9


K-313
N
CH
singlebond
Me
H
H
5
7


K-314
N
CH
singlebond
Me
H
H
5
8


K-315
N
CH
singlebond
Me
H
H
5
9


K-316
N
CH
singlebond
H
H
Me
1
7


K-317
N
CH
singlebond
H
H
Me
1
8


K-318
N
CH
singlebond
H
H
Me
1
9


K-319
N
CH
singlebond
H
H
Me
2
7


K-320
N
CH
singlebond
H
H
Me
2
8


K-321
N
CH
singlebond
H
H
Me
2
9


K-322
N
CH
singlebond
H
H
Me
3
7


K-323
N
CH
singlebond
H
H
Me
3
8


K-324
N
CH
singlebond
H
H
Me
3
9


K-325
N
CH
singlebond
H
H
Me
4
7


K-326
N
CH
singlebond
H
H
Me
4
8


K-327
N
CH
singlebond
H
H
Me
4
9


K-328
N
CH
singlebond
H
H
Me
5
7


K-329
N
CH
singlebond
H
H
Me
5
8


K-330
N
CH
singlebond
H
H
Me
5
9
























TABLE 44





Compound










No.
G1
G2
Q1
Ra
Rb
Rc
n
m







K-331
N
CH
singlebond
Me
Me
H
1
7


K-332
N
CH
singlebond
Me
Me
H
1
8


K-333
N
CH
singlebond
Me
Me
H
1
9


K-334
N
CH
singlebond
Me
Me
H
2
7


K-335
N
CH
singlebond
Me
Me
H
2
8


K-336
N
CH
singlebond
Me
Me
H
2
9


K-337
N
CH
singlebond
Me
Me
H
3
7


K-338
N
CH
singlebond
Me
Me
H
3
8


K-339
N
CH
singlebond
Me
Me
H
3
9


K-340
N
CH
singlebond
Me
Me
H
4
7


K-341
N
CH
singlebond
Me
Me
H
4
8


K-342
N
CH
singlebond
Me
Me
H
4
9


K-343
N
CH
singlebond
Me
Me
H
5
7


K-344
N
CH
singlebond
Me
Me
H
5
8


K-345
N
CH
singlebond
Me
Me
H
5
9


K-346
N
CH
singlebond
H
Me
Me
1
7


K-347
N
CH
singlebond
H
Me
Me
1
8


K-348
N
CH
singlebond
H
Me
Me
1
9


K-349
N
CH
singlebond
H
Me
Me
2
7


K-350
N
CH
singlebond
H
Me
Me
2
8


K-351
N
CH
singlebond
H
Me
Me
2
9


K-352
N
CH
singlebond
H
Me
Me
3
7


K-353
N
CH
singlebond
H
Me
Me
3
8


K-354
N
CH
singlebond
H
Me
Me
3
9


K-355
N
CH
singlebond
H
Me
Me
4
7


K-356
N
CH
singlebond
H
Me
Me
4
8


K-357
N
CH
singlebond
H
Me
Me
4
9


K-358
N
CH
singlebond
H
Me
Me
5
7


K-359
N
CH
singlebond
H
Me
Me
5
8


K-360
N
CH
singlebond
H
Me
Me
5
9


K-361
CH
N
—O—
Me
H
H
1
7


K-362
CH
N
—O—
Me
H
H
1
8


K-363
CH
N
—O—
Me
H
H
1
9


K-364
CH
N
—O—
Me
H
H
2
7


K-365
CH
N
—O—
Me
H
H
2
8


K-366
CH
N
—O—
Me
H
H
2
9


K-367
CH
N
—O—
Me
H
H
3
7


K-368
CH
N
—O—
Me
H
H
3
8


K-369
CH
N
—O—
Me
H
H
3
9


K-370
CH
N
—O—
Me
H
H
4
7


K-371
CH
N
—O—
Me
H
H
4
8


K-372
CH
N
—O—
Me
H
H
4
9


K-373
CH
N
—O—
Me
H
H
5
7


K-374
CH
N
—O—
Me
H
H
5
8


K-375
CH
N
—O—
Me
H
H
5
9


K-376
CH
N
—O—
H
H
Me
1
7


K-377
CH
N
—O—
H
H
Me
1
8


K-378
CH
N
—O—
H
H
Me
1
9


K-379
CH
N
—O—
H
H
Me
2
7


K-380
CH
N
—O—
H
H
Me
2
8


K-381
CH
N
—O—
H
H
Me
2
9


K-382
CH
N
—O—
H
H
Me
3
7


K-383
CH
N
—O—
H
H
Me
3
8


K-384
CH
N
—O—
H
H
Me
3
9


K-385
CH
N
—O—
H
H
Me
4
7


K-386
CH
N
—O—
H
H
Me
4
8


K-387
CH
N
—O—
H
H
Me
4
9


K-388
CH
N
—O—
H
H
Me
5
7


K-389
CH
N
—O—
H
H
Me
5
8


K-390
CH
N
—O—
H
H
Me
5
9


K-391
CH
N
—O—
Me
Me
H
1
7


K-392
CH
N
—O—
Me
Me
H
1
8


K-393
CH
N
—O—
Me
Me
H
1
9


K-394
CH
N
—O—
Me
Me
H
2
7


K-395
CH
N
—O—
Me
Me
H
2
8


K-396
CH
N
—O—
Me
Me
H
2
9


K-397
CH
N
—O—
Me
Me
H
3
7


K-398
CH
N
—O—
Me
Me
H
3
8


K-399
CH
N
—O—
Me
Me
H
3
9


K-400
CH
N
—O—
Me
Me
H
4
7


K-401
CH
N
—O—
Me
Me
H
4
8


K-402
CH
N
—O—
Me
Me
H
4
9


K-403
CH
N
—O—
Me
Me
H
5
7


K-404
CH
N
—O—
Me
Me
H
5
8


K-405
CH
N
—O—
Me
Me
H
5
9


K-406
CH
N
—O—
H
Me
Me
1
7


K-407
CH
N
—O—
H
Me
Me
1
8


K-408
CH
N
—O—
H
Me
Me
1
9


K-409
CH
N
—O—
H
Me
Me
2
7


K-410
CH
N
—O—
H
Me
Me
2
8


K-411
CH
N
—O—
H
Me
Me
2
9


K-412
CH
N
—O—
H
Me
Me
3
7


K-413
CH
N
—O—
H
Me
Me
3
8


K-414
CH
N
—O—
H
Me
Me
3
9


K-415
CH
N
—O—
H
Me
Me
4
7


K-416
CH
N
—O—
H
Me
Me
4
8


K-417
CH
N
—O—
H
Me
Me
4
9


K-418
CH
N
—O—
H
Me
Me
5
7


K-419
CH
N
—O—
H
Me
Me
5
8


K-420
CH
N
—O—
H
Me
Me
5
9


K-421
CH
N
—CH2O—
Me
H
H
1
7


K-422
CH
N
—CH2O—
Me
H
H
1
8


K-423
CH
N
—CH2O—
Me
H
H
1
9


K-424
CH
N
—CH2O—
Me
H
H
2
7


K-425
CH
N
—CH2O—
Me
H
H
2
8


K-426
CH
N
—CH2O—
Me
H
H
2
9


K-427
CH
N
—CH2O—
Me
H
H
3
7


K-428
CH
N
—CH2O—
Me
H
H
3
8


K-429
CH
N
—CH2O—
Me
H
H
3
9


K-430
CH
N
—CH2O—
Me
H
H
4
7


K-431
CH
N
—CH2O—
Me
H
H
4
8


K-432
CH
N
—CH2O—
Me
H
H
4
9


K-433
CH
N
—CH2O—
Me
H
H
5
7


K-434
CH
N
—CH2O—
Me
H
H
5
8


K-435
CH
N
—CH2O—
Me
H
H
5
9


K-436
CH
N
—CH2O—
H
H
Me
1
7


K-437
CH
N
—CH2O—
H
H
Me
1
8


K-438
CH
N
—CH2O—
H
H
Me
1
9


K-439
CH
N
—CH2O—
H
H
Me
2
7


K-440
CH
N
—CH2O—
H
H
Me
2
8
























TABLE 45





Compound










No.
G1
G2
Q1
Ra
Rb
Rc
n
m







K-441
CH
N
—CH2O—
H
H
Me
2
9


K-442
CH
N
—CH2O—
H
H
Me
3
7


K-443
CH
N
—CH2O—
H
H
Me
3
8


K-444
CH
N
—CH2O—
H
H
Me
3
9


K-445
CH
N
—CH2O—
H
H
Me
4
7


K-446
CH
N
—CH2O—
H
H
Me
4
8


K-447
CH
N
—CH2O—
H
H
Me
4
9


K-448
CH
N
—CH2O—
H
H
Me
5
7


K-449
CH
N
—CH2O—
H
H
Me
5
8


K-450
CH
N
—CH2O—
H
H
Me
5
9


K-451
CH
N
—CH2O—
Me
Me
H
1
7


K-452
CH
N
—CH2O—
Me
Me
H
1
8


K-453
CH
N
—CH2O—
Me
Me
H
1
9


K-454
CH
N
—CH2O—
Me
Me
H
2
7


K-455
CH
N
—CH2O—
Me
Me
H
2
8


K-456
CH
N
—CH2O—
Me
Me
H
2
9


K-457
CH
N
—CH2O—
Me
Me
H
3
7


K-458
CH
N
—CH2O—
Me
Me
H
3
8


K-459
CH
N
—CH2O—
Me
Me
H
3
9


K-460
CH
N
—CH2O—
Me
Me
H
4
7


K-461
CH
N
—CH2O—
Me
Me
H
4
8


K-462
CH
N
—CH2O—
Me
Me
H
4
9


K-463
CH
N
—CH2O—
Me
Me
H
5
7


K-464
CH
N
—CH2O—
Me
Me
H
5
8


K-465
CH
N
—CH2O—
Me
Me
H
5
9


K-466
CH
N
—CH2O—
H
Me
Me
1
7


K-467
CH
N
—CH2O—
H
Me
Me
1
8


K-468
CH
N
—CH2O—
H
Me
Me
1
9


K-469
CH
N
—CH2O—
H
Me
Me
2
7


K-470
CH
N
—CH2O—
H
Me
Me
2
8


K-471
CH
N
—CH2O—
H
Me
Me
2
9


K-472
CH
N
—CH2O—
H
Me
Me
3
7


K-473
CH
N
—CH2O—
H
Me
Me
3
8


K-474
CH
N
—CH2O—
H
Me
Me
3
9


K-475
CH
N
—CH2O—
H
Me
Me
4
7


K-476
CH
N
—CH2O—
H
Me
Me
4
8


K-477
CH
N
—CH2O—
H
Me
Me
4
9


K-478
CH
N
—CH2O—
H
Me
Me
5
7


K-479
CH
N
—CH2O—
H
Me
Me
5
8


K-480
CH
N
—CH2O—
H
Me
Me
5
9


K-481
CH
N
singlebond
Me
H
H
1
7


K-482
CH
N
singlebond
Me
H
H
1
8


K-483
CH
N
singlebond
Me
H
H
1
9


K-484
CH
N
singlebond
Me
H
H
2
7


K-485
CH
N
singlebond
Me
H
H
2
8


K-486
CH
N
singlebond
Me
H
H
2
9


K-487
CH
N
singlebond
Me
H
H
3
7


K-488
CH
N
singlebond
Me
H
H
3
8


K-489
CH
N
singlebond
Me
H
H
3
9


K-490
CH
N
singlebond
Me
H
H
4
7


K-491
CH
N
singlebond
Me
H
H
4
8


K-492
CH
N
singlebond
Me
H
H
4
9


K-493
CH
N
singlebond
Me
H
H
5
7


K-494
CH
N
singlebond
Me
H
H
5
8


K-495
CH
N
singlebond
Me
H
H
5
9


K-496
CH
N
singlebond
H
H
Me
1
7


K-497
CH
N
singlebond
H
H
Me
1
8


K-498
CH
N
singlebond
H
H
Me
1
9


K-499
CH
N
singlebond
H
H
Me
2
7


K-500
CH
N
singlebond
H
H
Me
2
8


K-501
CH
N
singlebond
H
H
Me
2
9


K-502
CH
N
singlebond
H
H
Me
3
7


K-503
CH
N
singlebond
H
H
Me
3
8


K-504
CH
N
singlebond
H
H
Me
3
9


K-505
CH
N
singlebond
H
H
Me
4
7


K-506
CH
N
singlebond
H
H
Me
4
8


K-507
CH
N
singlebond
H
H
Me
4
9


K-508
CH
N
singlebond
H
H
Me
5
7


K-509
CH
N
singlebond
H
H
Me
5
8


K-510
CH
N
singlebond
H
H
Me
5
9


K-511
CH
N
singlebond
Me
Me
H
1
7


K-512
CH
N
singlebond
Me
Me
H
1
8


K-513
CH
N
singlebond
Me
Me
H
1
9


K-514
CH
N
singlebond
Me
Me
H
2
7


K-515
CH
N
singlebond
Me
Me
H
2
8


K-516
CH
N
singlebond
Me
Me
H
2
9


K-517
CH
N
singlebond
Me
Me
H
3
7


K-518
CH
N
singlebond
Me
Me
H
3
8


K-519
CH
N
singlebond
Me
Me
H
3
9


K-520
CH
N
singlebond
Me
Me
H
4
7


K-521
CH
N
singlebond
Me
Me
H
4
8


K-522
CH
N
singlebond
Me
Me
H
4
9


K-523
CH
N
singlebond
Me
Me
H
5
7


K-524
CH
N
singlebond
Me
Me
H
5
8


K-525
CH
N
singlebond
Me
Me
H
5
9


K-526
CH
N
singlebond
H
Me
Me
1
7


K-527
CH
N
singlebond
H
Me
Me
1
8


K-528
CH
N
singlebond
H
Me
Me
1
9


K-529
CH
N
singlebond
H
Me
Me
2
7


K-530
CH
N
singlebond
H
Me
Me
2
8


K-531
CH
N
singlebond
H
Me
Me
2
9


K-532
CH
N
singlebond
H
Me
Me
3
7


K-533
CH
N
singlebond
H
Me
Me
3
8


K-534
CH
N
singlebond
H
Me
Me
3
9


K-535
CH
N
singlebond
H
Me
Me
4
7


K-536
CH
N
singlebond
H
Me
Me
4
8


K-537
CH
N
singlebond
H
Me
Me
4
9


K-538
CH
N
singlebond
H
Me
Me
5
7


K-539
CH
N
singlebond
H
Me
Me
5
8


K-540
CH
N
singlebond
H
Me
Me
5
9











embedded image
















TABLE 46







Compound








No.
G1
G2
Q1
n
m









L-1
CH
CH
—O—
1
7



L-2
CH
CH
—O—
1
8



L-3
CH
CH
—O—
1
9



L-4
CH
CH
—O—
2
7



L-5
CH
CH
—O—
2
8



L-6
CH
CH
—O—
2
9



L-7
CH
CH
—O—
3
7



L-8
CH
CH
—O—
3
8



L-9
CH
CH
—O—
3
9



L-10
CH
CH
—O—
4
7



L-11
CH
CH
—O—
4
8



L-12
CH
CH
—O—
4
9



L-13
CH
CH
—O—
5
7



L-14
CH
CH
—O—
5
8



L-15
CH
CH
—O—
5
9



L-16
CH
CH
—CH2O—
1
7



L-17
CH
CH
—CH2O—
1
8



L-18
CH
CH
—CH2O—
1
9



L-19
CH
CH
—CH2O—
2
7



L-20
CH
CH
—CH2O—
2
8



L-21
CH
CH
—CH2O—
2
9



L-22
CH
CH
—CH2O—
3
7



L-23
CH
CH
—CH2O—
3
8



L-24
CH
CH
—CH2O—
3
9



L-25
CH
CH
—CH2O—
4
7



L-26
CH
CH
—CH2O—
4
8



L-27
CH
CH
—CH2O—
4
9



L-28
CH
CH
—CH2O—
5
7



L-29
CH
CH
—CH2O—
5
8



L-30
CH
CH
—CH2O—
5
9



L-31
CH
CH
singlebond
1
7



L-32
CH
CH
singlebond
1
8



L-33
CH
CH
singlebond
1
9



L-34
CH
CH
singlebond
2
7



L-35
CH
CH
singlebond
2
8



L-36
CH
CH
singlebond
2
9



L-37
CH
CH
singlebond
3
7



L-38
CH
CH
singlebond
3
8



L-39
CH
CH
singlebond
3
9



L-40
CH
CH
singlebond
4
7



L-41
CH
CH
singlebond
4
8



L-42
CH
CH
singlebond
4
9



L-43
CH
CH
singlebond
5
7



L-44
CH
CH
singlebond
5
8



L-45
CH
CH
singlebond
5
9



L-46
N
CH
—O—
1
7



L-47
N
CH
—O—
1
8



L-48
N
CH
—O—
1
9



L-49
N
CH
—O—
2
7



L-50
N
CH
—O—
2
8



L-51
N
CH
—O—
2
9



L-52
N
CH
—O—
3
7



L-53
N
CH
—O—
3
8



L-54
N
CH
—O—
3
9



L-55
N
CH
—O—
4
7



L-56
N
CH
—O—
4
8



L-57
N
CH
—O—
4
9



L-58
N
CH
—O—
5
7



L-59
N
CH
—O—
5
8



L-60
N
CH
—O—
5
9



L-61
N
CH
—CH2O—
1
7



L-62
N
CH
—CH2O—
1
8



L-63
N
CH
—CH2O—
1
9



L-64
N
CH
—CH2O—
2
7



L-65
N
CH
—CH2O—
2
8



L-66
N
CH
—CH2O—
2
9



L-67
N
CH
—CH2O—
3
7



L-68
N
CH
—CH2O—
3
8



L-69
N
CH
—CH2O—
3
9



L-70
N
CH
—CH2O—
4
7



L-71
N
CH
—CH2O—
4
8



L-72
N
CH
—CH2O—
4
9



L-73
N
CH
—CH2O—
5
7



L-74
N
CH
—CH2O—
5
8



L-75
N
CH
—CH2O—
5
9



L-76
N
CH
singlebond
1
7



L-77
N
CH
singlebond
1
8



L-78
N
CH
singlebond
1
9



L-79
N
CH
singlebond
2
7



L-80
N
CH
singlebond
2
8



L-81
N
CH
singlebond
2
9



L-82
N
CH
singlebond
3
7



L-83
N
CH
singlebond
3
8



L-84
N
CH
singlebond
3
9



L-85
N
CH
singlebond
4
7



L-86
N
CH
singlebond
4
8



L-87
N
CH
singlebond
4
9



L-88
N
CH
singlebond
5
7



L-89
N
CH
singlebond
5
8



L-90
N
CH
singlebond
5
9



L-91
CH
N
—O—
1
7



L-92
CH
N
—O—
1
8



L-93
CH
N
—O—
1
9



L-94
CH
N
—O—
2
7



L-95
CH
N
—O—
2
8



L-96
CH
N
—O—
2
9



L-97
CH
N
—O—
3
7



L-98
CH
N
—O—
3
8



L-99
CH
N
—O—
3
9



L-100
CH
N
—O—
4
7



L-101
CH
N
—O—
4
8



L-102
CH
N
—O—
4
9



L-103
CH
N
—O—
5
7



L-104
CH
N
—O—
5
8



L-105
CH
N
—O—
5
9



L-106
CH
N
—CH2O—
1
7



L-107
CH
N
—CH2O—
1
8



L-108
CH
N
—CH2O—
1
9



L-109
CH
N
—CH2O—
2
7



L-110
CH
N
—CH2O—
2
8
























TABLE 47







Compound








No.
G1
G2
Q1
n
m









L-111
CH
N
—CH2O—
2
9



L-112
CH
N
—CH2O—
3
7



L-113
CH
N
—CH2O—
3
8



L-114
CH
N
—CH2O—
3
9



L-115
CH
N
—CH2O—
4
7



L-116
CH
N
—CH2O—
4
8



L-117
CH
N
—CH2O—
4
9



L-118
CH
N
—CH2O—
5
7



L-119
CH
N
—CH2O—
5
8



L-120
CH
N
—CH2O—
5
9



L-121
CH
N
singlebond
1
7



L-122
CH
N
singlebond
1
8



L-123
CH
N
singlebond
1
9



L-124
CH
N
singlebond
2
7



L-125
CH
N
singlebond
2
8



L-126
CH
N
singlebond
2
9



L-127
CH
N
singlebond
3
7



L-128
CH
N
singlebond
3
8



L-129
CH
N
singlebond
3
9



L-130
CH
N
singlebond
4
7



L-131
CH
N
singlebond
4
8



L-132
CH
N
singlebond
4
9



L-133
CH
N
singlebond
5
7



L-134
CH
N
singlebond
5
8



L-135
CH
N
singlebond
5
9












embedded image
















TABLE 48







Compound








No.
G1
G2
Q1
n
m









M-1
CH
CH
—O—
1
7



M-2
CH
CH
—O—
1
8



M-3
CH
CH
—O—
1
9



M-4
CH
CH
—O—
2
7



M-5
CH
CH
—O—
2
8



M-6
CH
CH
—O—
2
9



M-7
CH
CH
—O—
3
7



M-8
CH
CH
—O—
3
8



M-9
CH
CH
—O—
3
9



M-10
CH
CH
—O—
4
7



M-11
CH
CH
—O—
4
8



M-12
CH
CH
—O—
4
9



M-13
CH
CH
—O—
5
7



M-14
CH
CH
—O—
5
8



M-15
CH
CH
—O—
5
9



M-16
CH
CH
—CH2O—
1
7



M-17
CH
CH
—CH2O—
1
8



M-18
CH
CH
—CH2O—
1
9



M-19
CH
CH
—CH2O—
2
7



M-20
CH
CH
—CH2O—
2
8



M-21
CH
CH
—CH2O—
2
9



M-22
CH
CH
—CH2O—
3
7



M-23
CH
CH
—CH2O—
3
8



M-24
CH
CH
—CH2O—
3
9



M-25
CH
CH
—CH2O—
4
7



M-26
CH
CH
—CH2O—
4
8



M-27
CH
CH
—CH2O—
4
9



M-28
CH
CH
—CH2O—
5
7



M-29
CH
CH
—CH2O—
5
8



M-30
CH
CH
—CH2O—
5
9



M-31
CH
CH
singlebond
1
7



M-32
CH
CH
singlebond
1
8



M-33
CH
CH
singlebond
1
9



M-34
CH
CH
singlebond
2
7



M-35
CH
CH
singlebond
2
8



M-36
CH
CH
singlebond
2
9



M-37
CH
CH
singlebond
3
7



M-38
CH
CH
singlebond
3
8



M-39
CH
CH
singlebond
3
9



M-40
CH
CH
singlebond
4
7



M-41
CH
CH
singlebond
4
8



M-42
CH
CH
singlebond
4
9



M-43
CH
CH
singlebond
5
7



M-44
CH
CH
singlebond
5
8



M-45
CH
CH
singlebond
5
9



M-46
N
CH
—O—
1
7



M-47
N
CH
—O—
1
8



M-48
N
CH
—O—
1
9



M-49
N
CH
—O—
2
7



M-50
N
CH
—O—
2
8



M-51
N
CH
—O—
2
9



M-52
N
CH
—O—
3
7



M-53
N
CH
—O—
3
8



M-54
N
CH
—O—
3
9



M-55
N
CH
—O—
4
7



M-56
N
CH
—O—
4
8



M-57
N
CH
—O—
4
9



M-58
N
CH
—O—
5
7



M-59
N
CH
—O—
5
8



M-60
N
CH
—O—
5
9



M-61
N
CH
—CH2O—
1
7



M-62
N
CH
—CH2O—
1
8



M-63
N
CH
—CH2O—
1
9



M-64
N
CH
—CH2O—
2
7



M-65
N
CH
—CH2O—
2
8



M-66
N
CH
—CH2O—
2
9



M-67
N
CH
—CH2O—
3
7



M-68
N
CH
—CH2O—
3
8



M-69
N
CH
—CH2O—
3
9



M-70
N
CH
—CH2O—
4
7



M-71
N
CH
—CH2O—
4
8



M-72
N
CH
—CH2O—
4
9



M-73
N
CH
—CH2O—
5
7



M-74
N
CH
—CH2O—
5
8



M-75
N
CH
—CH2O—
5
9



M-76
N
CH
singlebond
1
7



M-77
N
CH
singlebond
1
8



M-78
N
CH
singlebond
1
9



M-79
N
CH
singlebond
2
7



M-80
N
CH
singlebond
2
8



M-81
N
CH
singlebond
2
9



M-82
N
CH
singlebond
3
7



M-83
N
CH
singlebond
3
8



M-84
N
CH
singlebond
3
9



M-85
N
CH
singlebond
4
7



M-86
N
CH
singlebond
4
8



M-87
N
CH
singlebond
4
9



M-88
N
CH
singlebond
5
7



M-89
N
CH
singlebond
5
8



M-90
N
CH
singlebond
5
9



M-91
CH
N
—O—
1
7



M-92
CH
N
—O—
1
8



M-93
CH
N
—O—
1
9



M-94
CH
N
—O—
2
7



M-95
CH
N
—O—
2
8



M-96
CH
N
—O—
2
9



M-97
CH
N
—O—
3
7



M-98
CH
N
—O—
3
8



M-99
CH
N
—O—
3
9



M-100
CH
N
—O—
4
7



M-101
CH
N
—O—
4
8



M-102
CH
N
—O—
4
9



M-103
CH
N
—O—
5
7



M-104
CH
N
—O—
5
8



M-105
CH
N
—O—
5
9



M-106
CH
N
—CH2O—
1
7



M-107
CH
N
—CH2O—
1
8



M-108
CH
N
—CH2O—
1
9



M-109
CH
N
—CH2O—
2
7



M-110
CH
N
—CH2O—
2
8
























TABLE 49







Compound








No.
G1
G2
Q1
n
m









M-111
CH
N
—CH2O—
2
9



M-112
CH
N
—CH2O—
3
7



M-113
CH
N
—CH2O—
3
8



M-114
CH
N
—CH2O—
3
9



M-115
CH
N
—CH2O—
4
7



M-116
CH
N
—CH2O—
4
8



M-117
CH
N
—CH2O—
4
9



M-118
CH
N
—CH2O—
5
7



M-119
CH
N
—CH2O—
5
8



M-120
CH
N
—CH2O—
5
9



M-121
CH
N
singlebond
1
7



M-122
CH
N
singlebond
1
8



M-123
CH
N
singlebond
1
9



M-124
CH
N
singlebond
2
7



M-125
CH
N
singlebond
2
8



M-126
CH
N
singlebond
2
9



M-127
CH
N
singlebond
3
7



M-128
CH
N
singlebond
3
8



M-129
CH
N
singlebond
3
9



M-130
CH
N
singlebond
4
7



M-131
CH
N
singlebond
4
8



M-132
CH
N
singlebond
4
9



M-133
CH
N
singlebond
5
7



M-134
CH
N
singlebond
5
8



M-135
CH
N
singlebond
5
9












embedded image

















TABLE 50







Compound









No.
G1
G2
Q1
Ra
n
m









N-1
CH
CH
—O—
H
1
7



N-2
CH
CH
—O—
H
1
8



N-3
CH
CH
—O—
H
1
9



N-4
CH
CH
—O—
H
2
7



N-5
CH
CH
—O—
H
2
8



N-6
CH
CH
—O—
H
2
9



N-7
CH
CH
—O—
H
3
7



N-8
CH
CH
—O—
H
3
8



N-9
CH
CH
—O—
H
3
9



N-10
CH
CH
—O—
H
4
7



N-11
CH
CH
—O—
H
4
8



N-12
CH
CH
—O—
H
4
9



N-13
CH
CH
—O—
H
5
7



N-14
CH
CH
—O—
H
5
8



N-15
CH
CH
—O—
H
5
9



N-16
CH
CH
—O—
Me
1
7



N-17
CH
CH
—O—
Me
1
8



N-18
CH
CH
—O—
Me
1
9



N-19
CH
CH
—O—
Me
2
7



N-20
CH
CH
—O—
Me
2
8



N-21
CH
CH
—O—
Me
2
9



N-22
CH
CH
—O—
Me
3
7



N-23
CH
CH
—O—
Me
3
8



N-24
CH
CH
—O—
Me
3
9



N-25
CH
CH
—O—
Me
4
7



N-26
CH
CH
—O—
Me
4
8



N-27
CH
CH
—O—
Me
4
9



N-28
CH
CH
—O—
Me
5
7



N-29
CH
CH
—O—
Me
5
8



N-30
CH
CH
—O—
Me
5
9



N-31
CH
CH
—CH2O—
H
1
7



N-32
CH
CH
—CH2O—
H
1
8



N-33
CH
CH
—CH2O—
H
1
9



N-34
CH
CH
—CH2O—
H
2
7



N-35
CH
CH
—CH2O—
H
2
8



N-36
CH
CH
—CH2O—
H
2
9



N-37
CH
CH
—CH2O—
H
3
7



N-38
CH
CH
—CH2O—
H
3
8



N-39
CH
CH
—CH2O—
H
3
9



N-40
CH
CH
—CH2O—
H
4
7



N-41
CH
CH
—CH2O—
H
4
8



N-42
CH
CH
—CH2O—
H
4
9



N-43
CH
CH
—CH2O—
H
5
7



N-44
CH
CH
—CH2O—
H
5
8



N-45
CH
CH
—CH2O—
H
5
9



N-46
CH
CH
—CH2O—
Me
1
7



N-47
CH
CH
—CH2O—
Me
1
8



N-48
CH
CH
—CH2O—
Me
1
9



N-49
CH
CH
—CH2O—
Me
2
7



N-50
CH
CH
—CH2O—
Me
2
8



N-51
CH
CH
—CH2O—
Me
2
9



N-52
CH
CH
—CH2O—
Me
3
7



N-53
CH
CH
—CH2O—
Me
3
8



N-54
CH
CH
—CH2O—
Me
3
9



N-55
CH
CH
—CH2O—
Me
4
7



N-56
CH
CH
—CH2O—
Me
4
8



N-57
CH
CH
—CH2O—
Me
4
9



N-58
CH
CH
—CH2O—
Me
5
7



N-59
CH
CH
—CH2O—
Me
5
8



N-60
CH
CH
—CH2O—
Me
5
9



N-61
CH
CH
singlebond
H
1
7



N-62
CH
CH
singlebond
H
1
8



N-63
CH
CH
singlebond
H
1
9



N-64
CH
CH
singlebond
H
2
7



N-65
CH
CH
singlebond
H
2
8



N-66
CH
CH
singlebond
H
2
9



N-67
CH
CH
singlebond
H
3
7



N-68
CH
CH
singlebond
H
3
8



N-69
CH
CH
singlebond
H
3
9



N-70
CH
CH
singlebond
H
4
7



N-71
CH
CH
singlebond
H
4
8



N-72
CH
CH
singlebond
H
4
9



N-73
CH
CH
singlebond
H
5
7



N-74
CH
CH
singlebond
H
5
8



N-75
CH
CH
singlebond
H
5
9



N-76
CH
CH
singlebond
Me
1
7



N-77
CH
CH
singlebond
Me
1
8



N-78
CH
CH
singlebond
Me
1
9



N-79
CH
CH
singlebond
Me
2
7



N-80
CH
CH
singlebond
Me
2
8



N-81
CH
CH
singlebond
Me
2
9



N-82
CH
CH
singlebond
Me
3
7



N-83
CH
CH
singlebond
Me
3
8



N-84
CH
CH
singlebond
Me
3
9



N-85
CH
CH
singlebond
Me
4
7



N-86
CH
CH
singlebond
Me
4
8



N-87
CH
CH
singlebond
Me
4
9



N-88
CH
CH
singlebond
Me
5
7



N-89
CH
CH
singlebond
Me
5
8



N-90
CH
CH
singlebond
Me
5
9



N-91
N
CH
—O—
H
1
7



N-92
N
CH
—O—
H
1
8



N-93
N
CH
—O—
H
1
9



N-94
N
CH
—O—
H
2
7



N-95
N
CH
—O—
H
2
8



N-96
N
CH
—O—
H
2
9



N-97
N
CH
—O—
H
3
7



N-98
N
CH
—O—
H
3
8



N-99
N
CH
—O—
H
3
9



N-100
N
CH
—O—
H
4
7



N-101
N
CH
—O—
H
4
8



N-102
N
CH
—O—
H
4
9



N-103
N
CH
—O—
H
5
7



N-104
N
CH
—O—
H
5
8



N-105
N
CH
—O—
H
5
9



N-106
N
CH
—O—
Me
1
7



N-107
N
CH
—O—
Me
1
8



N-108
N
CH
—O—
Me
1
9



N-109
N
CH
—O—
Me
2
7



N-110
N
CH
—O—
Me
2
8

























TABLE 51







Compound









No.
G1
G2
Q1
Ra
n
m









N-111
N
CH
—O—
Me
2
9



N-112
N
CH
—O—
Me
3
7



N-113
N
CH
—O—
Me
3
8



N-114
N
CH
—O—
Me
3
9



N-115
N
CH
—O—
Me
4
7



N-116
N
CH
—O—
Me
4
8



N-117
N
CH
—O—
Me
4
9



N-118
N
CH
—O—
Me
5
7



N-119
N
CH
—O—
Me
5
8



N-120
N
CH
—O—
Me
5
9



N-121
N
CH
—CH2O—
H
1
7



N-122
N
CH
—CH2O—
H
1
8



N-123
N
CH
—CH2O—
H
1
9



N-124
N
CH
—CH2O—
H
2
7



N-125
N
CH
—CH2O—
H
2
8



N-126
N
CH
—CH2O—
H
2
9



N-127
N
CH
—CH2O—
H
3
7



N-128
N
CH
—CH2O—
H
3
8



N-129
N
CH
—CH2O—
H
3
9



N-130
N
CH
—CH2O—
H
4
7



N-131
N
CH
—CH2O—
H
4
8



N-132
N
CH
—CH2O—
H
4
9



N-133
N
CH
—CH2O—
H
5
7



N-134
N
CH
—CH2O—
H
5
8



N-135
N
CH
—CH2O—
H
5
9



N-136
N
CH
—CH2O—
Me
1
7



N-137
N
CH
—CH2O—
Me
1
8



N-138
N
CH
—CH2O—
Me
1
9



N-139
N
CH
—CH2O—
Me
2
7



N-140
N
CH
—CH2O—
Me
2
8



N-141
N
CH
—CH2O—
Me
2
9



N-142
N
CH
—CH2O—
Me
3
7



N-143
N
CH
—CH2O—
Me
3
8



N-144
N
CH
—CH2O—
Me
3
9



N-145
N
CH
—CH2O—
Me
4
7



N-146
N
CH
—CH2O—
Me
4
8



N-147
N
CH
—CH2O—
Me
4
9



N-148
N
CH
—CH2O—
Me
5
7



N-149
N
CH
—CH2O—
Me
5
8



N-150
N
CH
—CH2O—
Me
5
9



N-151
N
CH
singlebond
H
1
7



N-152
N
CH
singlebond
H
1
8



N-153
N
CH
singlebond
H
1
9



N-154
N
CH
singlebond
H
2
7



N-155
N
CH
singlebond
H
2
8



N-156
N
CH
singlebond
H
2
9



N-157
N
CH
singlebond
H
3
7



N-158
N
CH
singlebond
H
3
8



N-159
N
CH
singlebond
H
3
9



N-160
N
CH
singlebond
H
4
7



N-161
N
CH
singlebond
H
4
8



N-162
N
CH
singlebond
H
4
9



N-163
N
CH
singlebond
H
5
7



N-164
N
CH
singlebond
H
5
8



N-165
N
CH
singlebond
H
5
9



N-166
N
CH
singlebond
Me
1
7



N-167
N
CH
singlebond
Me
1
8



N-168
N
CH
singlebond
Me
1
9



N-169
N
CH
singlebond
Me
2
7



N-170
N
CH
singlebond
Me
2
8



N-171
N
CH
singlebond
Me
2
9



N-172
N
CH
singlebond
Me
3
7



N-173
N
CH
singlebond
Me
3
8



N-174
N
CH
singlebond
Me
3
9



N-175
N
CH
singlebond
Me
4
7



N-176
N
CH
singlebond
Me
4
8



N-177
N
CH
singlebond
Me
4
9



N-178
N
CH
singlebond
Me
5
7



N-179
N
CH
singlebond
Me
5
8



N-180
N
CH
singlebond
Me
5
9



N-181
CH
N
—O—
H
1
7



N-182
CH
N
—O—
H
1
8



N-183
CH
N
—O—
H
1
9



N-184
CH
N
—O—
H
2
7



N-185
CH
N
—O—
H
2
8



N-186
CH
N
—O—
H
2
9



N-187
CH
N
—O—
H
3
7



N-188
CH
N
—O—
H
3
8



N-189
CH
N
—O—
H
3
9



N-190
CH
N
—O—
H
4
7



N-191
CH
N
—O—
H
4
8



N-192
CH
N
—O—
H
4
9



N-193
CH
N
—O—
H
5
7



N-194
CH
N
—O—
H
5
8



N-195
CH
N
—O—
H
5
9



N-196
CH
N
—O—
Me
1
7



N-197
CH
N
—O—
Me
1
8



N-198
CH
N
—O—
Me
1
9



N-199
CH
N
—O—
Me
2
7



N-200
CH
N
—O—
Me
2
8



N-201
CH
N
—O—
Me
2
9



N-202
CH
N
—O—
Me
3
7



N-203
CH
N
—O—
Me
3
8



N-204
CH
N
—O—
Me
3
9



N-205
CH
N
—O—
Me
4
7



N-206
CH
N
—O—
Me
4
8



N-207
CH
N
—O—
Me
4
9



N-208
CH
N
—O—
Me
5
7



N-209
CH
N
—O—
Me
5
8



N-210
CH
N
—O—
Me
5
9



N-211
CH
N
—CH2O—
H
1
7



N-212
CH
N
—CH2O—
H
1
8



N-213
CH
N
—CH2O—
H
1
9



N-214
CH
N
—CH2O—
H
2
7



N-215
CH
N
—CH2O—
H
2
8



N-216
CH
N
—CH2O—
H
2
9



N-217
CH
N
—CH2O—
H
3
7



N-218
CH
N
—CH2O—
H
3
8



N-219
CH
N
—CH2O—
H
3
9



N-220
CH
N
—CH2O—
H
4
7

























TABLE 52







Compound









No.
G1
G2
Q1
Ra
n
m









N-221
CH
N
—CH2O—
H
4
8



N-222
CH
N
—CH2O—
H
4
9



N-223
CH
N
—CH2O—
H
5
7



N-224
CH
N
—CH2O—
H
5
8



N-225
CH
N
—CH2O—
H
5
9



N-226
CH
N
—CH2O—
Me
1
7



N-227
CH
N
—CH2O—
Me
1
8



N-228
CH
N
—CH2O—
Me
1
9



N-229
CH
N
—CH2O—
Me
2
7



N-230
CH
N
—CH2O—
Me
2
8



N-231
CH
N
—CH2O—
Me
2
9



N-232
CH
N
—CH2O—
Me
3
7



N-233
CH
N
—CH2O—
Me
3
8



N-234
CH
N
—CH2O—
Me
3
9



N-235
CH
N
—CH2O—
Me
4
7



N-236
CH
N
—CH2O—
Me
4
8



N-237
CH
N
—CH2O—
Me
4
9



N-238
CH
N
—CH2O—
Me
5
7



N-239
CH
N
—CH2O—
Me
5
8



N-240
CH
N
—CH2O—
Me
5
9



N-241
CH
N
singlebond
H
1
7



N-242
CH
N
singlebond
H
1
8



N-243
CH
N
singlebond
H
1
9



N-244
CH
N
singlebond
H
2
7



N-245
CH
N
singlebond
H
2
8



N-246
CH
N
singlebond
H
2
9



N-247
CH
N
singlebond
H
3
7



N-248
CH
N
singlebond
H
3
8



N-249
CH
N
singlebond
H
3
9



N-250
CH
N
singlebond
H
4
7



N-251
CH
N
singlebond
H
4
8



N-252
CH
N
singlebond
H
4
9



N-253
CH
N
singlebond
H
5
7



N-254
CH
N
singlebond
H
5
8



N-255
CH
N
singlebond
H
5
9



N-256
CH
N
singlebond
Me
1
7



N-257
CH
N
singlebond
Me
1
8



N-258
CH
N
singlebond
Me
1
9



N-259
CH
N
singlebond
Me
2
7



N-260
CH
N
singlebond
Me
2
8



N-261
CH
N
singlebond
Me
2
9



N-262
CH
N
singlebond
Me
3
7



N-263
CH
N
singlebond
Me
3
8



N-264
CH
N
singlebond
Me
3
9



N-265
CH
N
singlebond
Me
4
7



N-266
CH
N
singlebond
Me
4
8



N-267
CH
N
singlebond
Me
4
9



N-268
CH
N
singlebond
Me
5
7



N-269
CH
N
singlebond
Me
5
8



N-270
CH
N
singlebond
Me
5
9












embedded image

















TABLE 53







Compound









No.
G1
G2
Q1
Ra
n
m









O-1
CH
CH
—O—
H
1
7



O-2
CH
CH
—O—
H
1
8



O-3
CH
CH
—O—
H
1
9



O-4
CH
CH
—O—
H
2
7



O-5
CH
CH
—O—
H
2
8



O-6
CH
CH
—O—
H
2
9



O-7
CH
CH
—O—
H
3
7



O-8
CH
CH
—O—
H
3
8



O-9
CH
CH
—O—
H
3
9



O-10
CH
CH
—O—
H
4
7



O-11
CH
CH
—O—
H
4
8



O-12
CH
CH
—O—
H
4
9



O-13
CH
CH
—O—
H
5
7



O-14
CH
CH
—O—
H
5
8



O-15
CH
CH
—O—
H
5
9



O-16
CH
CH
—O—
Me
1
7



O-17
CH
CH
—O—
Me
1
8



O-18
CH
CH
—O—
Me
1
9



O-19
CH
CH
—O—
Me
2
7



O-20
CH
CH
—O—
Me
2
8



O-21
CH
CH
—O—
Me
2
9



O-22
CH
CH
—O—
Me
3
7



O-23
CH
CH
—O—
Me
3
8



O-24
CH
CH
—O—
Me
3
9



O-25
CH
CH
—O—
Me
4
7



O-26
CH
CH
—O—
Me
4
8



O-27
CH
CH
—O—
Me
4
9



O-28
CH
CH
—O—
Me
5
7



O-29
CH
CH
—O—
Me
5
8



O-30
CH
CH
—O—
Me
5
9



O-31
CH
CH
—CH2O—
H
1
7



O-32
CH
CH
—CH2O—
H
1
8



O-33
CH
CH
—CH2O—
H
1
9



O-34
CH
CH
—CH2O—
H
2
7



O-35
CH
CH
—CH2O—
H
2
8



O-36
CH
CH
—CH2O—
H
2
9



O-37
CH
CH
—CH2O—
H
3
7



O-38
CH
CH
—CH2O—
H
3
8



O-39
CH
CH
—CH2O—
H
3
9



O-40
CH
CH
—CH2O—
H
4
7



O-41
CH
CH
—CH2O—
H
4
8



O-42
CH
CH
—CH2O—
H
4
9



O-43
CH
CH
—CH2O—
H
5
7



O-44
CH
CH
—CH2O—
H
5
8



O-45
CH
CH
—CH2O—
H
5
9



O-46
CH
CH
—CH2O—
Me
1
7



O-47
CH
CH
—CH2O—
Me
1
8



O-48
CH
CH
—CH2O—
Me
1
9



O-49
CH
CH
—CH2O—
Me
2
7



O-50
CH
CH
—CH2O—
Me
2
8



O-51
CH
CH
—CH2O—
Me
2
9



O-52
CH
CH
—CH2O—
Me
3
7



O-53
CH
CH
—CH2O—
Me
3
8



O-54
CH
CH
—CH2O—
Me
3
9



O-55
CH
CH
—CH2O—
Me
4
7



O-56
CH
CH
—CH2O—
Me
4
8



O-57
CH
CH
—CH2O—
Me
4
9



O-58
CH
CH
—CH2O—
Me
5
7



O-59
CH
CH
—CH2O—
Me
5
8



O-60
CH
CH
—CH2O—
Me
5
9



O-61
CH
CH
singlebond
H
1
7



O-62
CH
CH
singlebond
H
1
8



O-63
CH
CH
singlebond
H
1
9



O-64
CH
CH
singlebond
H
2
7



O-65
CH
CH
singlebond
H
2
8



O-66
CH
CH
singlebond
H
2
9



O-67
CH
CH
singlebond
H
3
7



O-68
CH
CH
singlebond
H
3
8



O-69
CH
CH
singlebond
H
3
9



O-70
CH
CH
singlebond
H
4
7



O-71
CH
CH
singlebond
H
4
8



O-72
CH
CH
singlebond
H
4
9



O-73
CH
CH
singlebond
H
5
7



O-74
CH
CH
singlebond
H
5
8



O-75
CH
CH
singlebond
H
5
9



O-76
CH
CH
singlebond
Me
1
7



O-77
CH
CH
singlebond
Me
1
8



O-78
CH
CH
singlebond
Me
1
9



O-79
CH
CH
singlebond
Me
2
7



O-80
CH
CH
singlebond
Me
2
8



O-81
CH
CH
singlebond
Me
2
9



O-82
CH
CH
singlebond
Me
3
7



O-83
CH
CH
singlebond
Me
3
8



O-84
CH
CH
singlebond
Me
3
9



O-85
CH
CH
singlebond
Me
4
7



O-86
CH
CH
singlebond
Me
4
8



O-87
CH
CH
singlebond
Me
4
9



O-88
CH
CH
singlebond
Me
5
7



O-89
CH
CH
singlebond
Me
5
8



O-90
CH
CH
singlebond
Me
5
9



O-91
N
CH
—O—
H
1
7



O-92
N
CH
—O—
H
1
8



O-93
N
CH
—O—
H
1
9



O-94
N
CH
—O—
H
2
7



O-95
N
CH
—O—
H
2
8



O-96
N
CH
—O—
H
2
9



O-97
N
CH
—O—
H
3
7



O-98
N
CH
—O—
H
3
8



O-99
N
CH
—O—
H
3
9



O-100
N
CH
—O—
H
4
7



O-101
N
CH
—O—
H
4
8



O-102
N
CH
—O—
H
4
9



O-103
N
CH
—O—
H
5
7



O-104
N
CH
—O—
H
5
8



O-105
N
CH
—O—
H
5
9



O-106
N
CH
—O—
Me
1
7



O-107
N
CH
—O—
Me
1
8



O-108
N
CH
—O—
Me
1
9



O-109
N
CH
—O—
Me
2
7



O-110
N
CH
—O—
Me
2
8

























TABLE 54







Compound









No.
G1
G2
Q1
Ra
n
m









O-111
N
CH
—O—
Me
2
9



O-112
N
CH
—O—
Me
3
7



O-113
N
CH
—O—
Me
3
8



O-114
N
CH
—O—
Me
3
9



O-115
N
CH
—O—
Me
4
7



O-116
N
CH
—O—
Me
4
8



O-117
N
CH
—O—
Me
4
9



O-118
N
CH
—O—
Me
5
7



O-119
N
CH
—O—
Me
5
8



O-120
N
CH
—O—
Me
5
9



O-121
N
CH
—CH2O—
H
1
7



O-122
N
CH
—CH2O—
H
1
8



O-123
N
CH
—CH2O—
H
1
9



O-124
N
CH
—CH2O—
H
2
7



O-125
N
CH
—CH2O—
H
2
8



O-126
N
CH
—CH2O—
H
2
9



O-127
N
CH
—CH2O—
H
3
7



O-128
N
CH
—CH2O—
H
3
8



O-129
N
CH
—CH2O—
H
3
9



O-130
N
CH
—CH2O—
H
4
7



O-131
N
CH
—CH2O—
H
4
8



O-132
N
CH
—CH2O—
H
4
9



O-133
N
CH
—CH2O—
H
5
7



O-134
N
CH
—CH2O—
H
5
8



O-135
N
CH
—CH2O—
H
5
9



O-136
N
CH
—CH2O—
Me
1
7



O-137
N
CH
—CH2O—
Me
1
8



O-138
N
CH
—CH2O—
Me
1
9



O-139
N
CH
—CH2O—
Me
2
7



O-140
N
CH
—CH2O—
Me
2
8



O-141
N
CH
—CH2O—
Me
2
9



O-142
N
CH
—CH2O—
Me
3
7



O-143
N
CH
—CH2O—
Me
3
8



O-144
N
CH
—CH2O—
Me
3
9



O-145
N
CH
—CH2O—
Me
4
7



O-146
N
CH
—CH2O—
Me
4
8



O-147
N
CH
—CH2O—
Me
4
9



O-148
N
CH
—CH2O—
Me
5
7



O-149
N
CH
—CH2O—
Me
5
8



O-150
N
CH
—CH2O—
Me
5
9



O-151
N
CH
singlebond
H
1
7



O-152
N
CH
singlebond
H
1
8



O-153
N
CH
singlebond
H
1
9



O-154
N
CH
singlebond
H
2
7



O-155
N
CH
singlebond
H
2
8



O-156
N
CH
singlebond
H
2
9



O-157
N
CH
singlebond
H
3
7



O-158
N
CH
singlebond
H
3
8



O-159
N
CH
singlebond
H
3
9



O-160
N
CH
singlebond
H
4
7



O-161
N
CH
singlebond
H
4
8



O-162
N
CH
singlebond
H
4
9



O-163
N
CH
singlebond
H
5
7



O-164
N
CH
singlebond
H
5
8



O-165
N
CH
singlebond
H
5
9



O-166
N
CH
singlebond
Me
1
7



O-167
N
CH
singlebond
Me
1
8



O-168
N
CH
singlebond
Me
1
9



O-169
N
CH
singlebond
Me
2
7



O-170
N
CH
singlebond
Me
2
8



O-171
N
CH
singlebond
Me
2
9



O-172
N
CH
singlebond
Me
3
7



O-173
N
CH
singlebond
Me
3
8



O-174
N
CH
singlebond
Me
3
9



O-175
N
CH
singlebond
Me
4
7



O-176
N
CH
singlebond
Me
4
8



O-177
N
CH
singlebond
Me
4
9



O-178
N
CH
singlebond
Me
5
7



O-179
N
CH
singlebond
Me
5
8



O-180
N
CH
singlebond
Me
5
9



O-181
CH
N
—O—
H
1
7



O-182
CH
N
—O—
H
1
8



O-183
CH
N
—O—
H
1
9



O-184
CH
N
—O—
H
2
7



O-185
CH
N
—O—
H
2
8



O-186
CH
N
—O—
H
2
9



O-187
CH
N
—O—
H
3
7



O-188
CH
N
—O—
H
3
8



O-189
CH
N
—O—
H
3
9



O-190
CH
N
—O—
H
4
7



O-191
CH
N
—O—
H
4
8



O-192
CH
N
—O—
H
4
9



O-193
CH
N
—O—
H
5
7



O-194
CH
N
—O—
H
5
8



O-195
CH
N
—O—
H
5
9



O-196
CH
N
—O—
Me
1
7



O-197
CH
N
—O—
Me
1
8



O-198
CH
N
—O—
Me
1
9



O-199
CH
N
—O—
Me
2
7



O-200
CH
N
—O—
Me
2
8



O-201
CH
N
—O—
Me
2
9



O-202
CH
N
—O—
Me
3
7



O-203
CH
N
—O—
Me
3
8



O-204
CH
N
—O—
Me
3
9



O-205
CH
N
—O—
Me
4
7



O-206
CH
N
—O—
Me
4
8



O-207
CH
N
—O—
Me
4
9



O-208
CH
N
—O—
Me
5
7



O-209
CH
N
—O—
Me
5
8



O-210
CH
N
—O—
Me
5
9



O-211
CH
N
—CH2O—
H
1
7



O-212
CH
N
—CH2O—
H
1
8



O-213
CH
N
—CH2O—
H
1
9



O-214
CH
N
—CH2O—
H
2
7



O-215
CH
N
—CH2O—
H
2
8



O-216
CH
N
—CH2O—
H
2
9



O-217
CH
N
—CH2O—
H
3
7



O-218
CH
N
—CH2O—
H
3
8



O-219
CH
N
—CH2O—
H
3
9



O-220
CH
N
—CH2O—
H
4
7

























TABLE 55







Compound









No.
G1
G2
Q1
Ra
n
m









O-221
CH
N
—CH2O—
H
4
8



O-222
CH
N
—CH2O—
H
4
9



O-223
CH
N
—CH2O—
H
5
7



O-224
CH
N
—CH2O—
H
5
8



O-225
CH
N
—CH2O—
H
5
9



O-226
CH
N
—CH2O—
Me
1
7



O-227
CH
N
—CH2O—
Me
1
8



O-228
CH
N
—CH2O—
Me
1
9



O-229
CH
N
—CH2O—
Me
2
7



O-230
CH
N
—CH2O—
Me
2
8



O-231
CH
N
—CH2O—
Me
2
9



O-232
CH
N
—CH2O—
Me
3
7



O-233
CH
N
—CH2O—
Me
3
8



O-234
CH
N
—CH2O—
Me
3
9



O-235
CH
N
—CH2O—
Me
4
7



O-236
CH
N
—CH2O—
Me
4
8



O-237
CH
N
—CH2O—
Me
4
9



O-238
CH
N
—CH2O—
Me
5
7



O-239
CH
N
—CH2O—
Me
5
8



O-240
CH
N
—CH2O—
Me
5
9



O-241
CH
N
singlebond
H
1
7



O-242
CH
N
singlebond
H
1
8



O-243
CH
N
singlebond
H
1
9



O-244
CH
N
singlebond
H
2
7



O-245
CH
N
singlebond
H
2
8



O-246
CH
N
singlebond
H
2
9



O-247
CH
N
singlebond
H
3
7



O-248
CH
N
singlebond
H
3
8



O-249
CH
N
singlebond
H
3
9



O-250
CH
N
singlebond
H
4
7



O-251
CH
N
singlebond
H
4
8



O-252
CH
N
singlebond
H
4
9



O-253
CH
N
singlebond
H
5
7



O-254
CH
N
singlebond
H
5
8



O-255
CH
N
singlebond
H
5
9



O-256
CH
N
singlebond
Me
1
7



O-257
CH
N
singlebond
Me
1
8



O-258
CH
N
singlebond
Me
1
9



O-259
CH
N
singlebond
Me
2
7



O-260
CH
N
singlebond
Me
2
8



O-261
CH
N
singlebond
Me
2
9



O-262
CH
N
singlebond
Me
3
7



O-263
CH
N
singlebond
Me
3
8



O-264
CH
N
singlebond
Me
3
9



O-265
CH
N
singlebond
Me
4
7



O-266
CH
N
singlebond
Me
4
8



O-267
CH
N
singlebond
Me
4
9



O-268
CH
N
singlebond
Me
5
7



O-269
CH
N
singlebond
Me
5
8



O-270
CH
N
singlebond
Me
5
9












embedded image
















TABLE 56







Compound








No.
G1
G2
Q1
n
m









P-1
CH
CH
—O—
1
7



P-2
CH
CH
—O—
1
8



P-3
CH
CH
—O—
1
9



P-4
CH
CH
—O—
2
7



P-5
CH
CH
—O—
2
8



P-6
CH
CH
—O—
2
9



P-7
CH
CH
—O—
3
7



P-8
CH
CH
—O—
3
8



P-9
CH
CH
—O—
3
9



P-10
CH
CH
—O—
4
7



P-11
CH
CH
—O—
4
8



P-12
CH
CH
—O—
4
9



P-13
CH
CH
—O—
5
7



P-14
CH
CH
—O—
5
8



P-15
CH
CH
—O—
5
9



P-16
CH
CH
—CH2O—
1
7



P-17
CH
CH
—CH2O—
1
8



P-18
CH
CH
—CH2O—
1
9



P-19
CH
CH
—CH2O—
2
7



P-20
CH
CH
—CH2O—
2
8



P-21
CH
CH
—CH2O—
2
9



P-22
CH
CH
—CH2O—
3
7



P-23
CH
CH
—CH2O—
3
8



P-24
CH
CH
—CH2O—
3
9



P-25
CH
CH
—CH2O—
4
7



P-26
CH
CH
—CH2O—
4
8



P-27
CH
CH
—CH2O—
4
9



P-28
CH
CH
—CH2O—
5
7



P-29
CH
CH
—CH2O—
5
8



P-30
CH
CH
—CH2O—
5
9



P-31
CH
CH
singlebond
1
7



P-32
CH
CH
singlebond
1
8



P-33
CH
CH
singlebond
1
9



P-34
CH
CH
singlebond
2
7



P-35
CH
CH
singlebond
2
8



P-36
CH
CH
singlebond
2
9



P-37
CH
CH
singlebond
3
7



P-38
CH
CH
singlebond
3
8



P-39
CH
CH
singlebond
3
9



P-40
CH
CH
singlebond
4
7



P-41
CH
CH
singlebond
4
8



P-42
CH
CH
singlebond
4
9



P-43
CH
CH
singlebond
5
7



P-44
CH
CH
singlebond
5
8



P-45
CH
CH
singlebond
5
9



P-46
N
CH
—O—
1
7



P-47
N
CH
—O—
1
8



P-48
N
CH
—O—
1
9



P-49
N
CH
—O—
2
7



P-50
N
CH
—O—
2
8



P-51
N
CH
—O—
2
9



P-52
N
CH
—O—
3
7



P-53
N
CH
—O—
3
8



P-54
N
CH
—O—
3
9



P-55
N
CH
—O—
4
7



P-56
N
CH
—O—
4
8



P-57
N
CH
—O—
4
9



P-58
N
CH
—O—
5
7



P-59
N
CH
—O—
5
8



P-60
N
CH
—O—
5
9



P-61
N
CH
—CH2O—
1
7



P-62
N
CH
—CH2O—
1
8



P-63
N
CH
—CH2O—
1
9



P-64
N
CH
—CH2O—
2
7



P-65
N
CH
—CH2O—
2
8



P-66
N
CH
—CH2O—
2
9



P-67
N
CH
—CH2O—
3
7



P-68
N
CH
—CH2O—
3
8



P-69
N
CH
—CH2O—
3
9



P-70
N
CH
—CH2O—
4
7



P-71
N
CH
—CH2O—
4
8



P-72
N
CH
—CH2O—
4
9



P-73
N
CH
—CH2O—
5
7



P-74
N
CH
—CH2O—
5
8



P-75
N
CH
—CH2O—
5
9



P-76
N
CH
singlebond
1
7



P-77
N
CH
singlebond
1
8



P-78
N
CH
singlebond
1
9



P-79
N
CH
singlebond
2
7



P-80
N
CH
singlebond
2
8



P-81
N
CH
singlebond
2
9



P-82
N
CH
singlebond
3
7



P-83
N
CH
singlebond
3
8



P-84
N
CH
singlebond
3
9



P-85
N
CH
singlebond
4
7



P-86
N
CH
singlebond
4
8



P-87
N
CH
singlebond
4
9



P-88
N
CH
singlebond
5
7



P-89
N
CH
singlebond
5
8



P-90
N
CH
singlebond
5
9



P-91
CH
N
—O—
1
7



P-92
CH
N
—O—
1
8



P-93
CH
N
—O—
1
9



P-94
CH
N
—O—
2
7



P-95
CH
N
—O—
2
8



P-96
CH
N
—O—
2
9



P-97
CH
N
—O—
3
7



P-98
CH
N
—O—
3
8



P-99
CH
N
—O—
3
9



P-100
CH
N
—O—
4
7



P-101
CH
N
—O—
4
8



P-102
CH
N
—O—
4
9



P-103
CH
N
—O—
5
7



P-104
CH
N
—O—
5
8



P-105
CH
N
—O—
5
9



P-106
CH
N
—CH2O—
1
7



P-107
CH
N
—CH2O—
1
8



P-108
CH
N
—CH2O—
1
9



P-109
CH
N
—CH2O—
2
7



P-110
CH
N
—CH2O—
2
8
























TABLE 57







Compound








No.
G1
G2
Q1
n
m









P-111
CH
N
—CH2O—
2
9



P-112
CH
N
—CH2O—
3
7



P-113
CH
N
—CH2O—
3
8



P-114
CH
N
—CH2O—
3
9



P-115
CH
N
—CH2O—
4
7



P-116
CH
N
—CH2O—
4
8



P-117
CH
N
—CH2O—
4
9



P-118
CH
N
—CH2O—
5
7



P-119
CH
N
—CH2O—
5
8



P-120
CH
N
—CH2O—
5
9



P-121
CH
N
singlebond
1
7



P-122
CH
N
singlebond
1
8



P-123
CH
N
singlebond
1
9



P-124
CH
N
singlebond
2
7



P-125
CH
N
singlebond
2
8



P-126
CH
N
singlebond
2
9



P-127
CH
N
singlebond
3
7



P-128
CH
N
singlebond
3
8



P-129
CH
N
singlebond
3
9



P-130
CH
N
singlebond
4
7



P-131
CH
N
singlebond
4
8



P-132
CH
N
singlebond
4
9



P-133
CH
N
singlebond
5
7



P-134
CH
N
singlebond
5
8



P-135
CH
N
singlebond
5
9












embedded image
















TABLE 58







Compound








No.
G1
G2
Q1
n
m









Q-1
CH
CH
—O—
1
7



Q-2
CH
CH
—O—
1
8



Q-3
CH
CH
—O—
1
9



Q-4
CH
CH
—O—
2
7



Q-5
CH
CH
—O—
2
8



Q-6
CH
CH
—O—
2
9



Q-7
CH
CH
—O—
3
7



Q-8
CH
CH
—O—
3
8



Q-9
CH
CH
—O—
3
9



Q-10
CH
CH
—O—
4
7



Q-11
CH
CH
—O—
4
8



Q-12
CH
CH
—O—
4
9



Q-13
CH
CH
—O—
5
7



Q-14
CH
CH
—O—
5
8



Q-15
CH
CH
—O—
5
9



Q-16
CH
CH
—CH2O—
1
7



Q-17
CH
CH
—CH2O—
1
8



Q-18
CH
CH
—CH2O—
1
9



Q-19
CH
CH
—CH2O—
2
7



Q-20
CH
CH
—CH2O—
2
8



Q-21
CH
CH
—CH2O—
2
9



Q-22
CH
CH
—CH2O—
3
7



Q-23
CH
CH
—CH2O—
3
8



Q-24
CH
CH
—CH2O—
3
9



Q-25
CH
CH
—CH2O—
4
7



Q-26
CH
CH
—CH2O—
4
8



Q-27
CH
CH
—CH2O—
4
9



Q-28
CH
CH
—CH2O—
5
7



Q-29
CH
CH
—CH2O—
5
8



Q-30
CH
CH
—CH2O—
5
9



Q-31
CH
CH
singlebond
1
7



Q-32
CH
CH
singlebond
1
8



Q-33
CH
CH
singlebond
1
9



Q-34
CH
CH
singlebond
2
7



Q-35
CH
CH
singlebond
2
8



Q-36
CH
CH
singlebond
2
9



Q-37
CH
CH
singlebond
3
7



Q-38
CH
CH
singlebond
3
8



Q-39
CH
CH
singlebond
3
9



Q-40
CH
CH
singlebond
4
7



Q-41
CH
CH
singlebond
4
8



Q-42
CH
CH
singlebond
4
9



Q-43
CH
CH
singlebond
5
7



Q-44
CH
CH
singlebond
5
8



Q-45
CH
CH
singlebond
5
9



Q-46
N
CH
—O—
1
7



Q-47
N
CH
—O—
1
8



Q-48
N
CH
—O—
1
9



Q-49
N
CH
—O—
2
7



Q-50
N
CH
—O—
2
8



Q-51
N
CH
—O—
2
9



Q-52
N
CH
—O—
3
7



Q-53
N
CH
—O—
3
8



Q-54
N
CH
—O—
3
9



Q-55
N
CH
—O—
4
7



Q-56
N
CH
—O—
4
8



Q-57
N
CH
—O—
4
9



Q-58
N
CH
—O—
5
7



Q-59
N
CH
—O—
5
8



Q-60
N
CH
—O—
5
9



Q-61
N
CH
—CH2O—
1
7



Q-62
N
CH
—CH2O—
1
8



Q-63
N
CH
—CH2O—
1
9



Q-64
N
CH
—CH2O—
2
7



Q-65
N
CH
—CH2O—
2
8



Q-66
N
CH
—CH2O—
2
9



Q-67
N
CH
—CH2O—
3
7



Q-68
N
CH
—CH2O—
3
8



Q-69
N
CH
—CH2O—
3
9



Q-70
N
CH
—CH2O—
4
7



Q-71
N
CH
—CH2O—
4
8



Q-72
N
CH
—CH2O—
4
9



Q-73
N
CH
—CH2O—
5
7



Q-74
N
CH
—CH2O—
5
8



Q-75
N
CH
—CH2O—
5
9



Q-76
N
CH
singlebond
1
7



Q-77
N
CH
singlebond
1
8



Q-78
N
CH
singlebond
1
9



Q-79
N
CH
singlebond
2
7



Q-80
N
CH
singlebond
2
8



Q-81
N
CH
singlebond
2
9



Q-82
N
CH
singlebond
3
7



Q-83
N
CH
singlebond
3
8



Q-84
N
CH
singlebond
3
9



Q-85
N
CH
singlebond
4
7



Q-86
N
CH
singlebond
4
8



Q-87
N
CH
singlebond
4
9



Q-88
N
CH
singlebond
5
7



Q-89
N
CH
singlebond
5
8



Q-90
N
CH
singlebond
5
9



Q-91
CH
N
—O—
1
7



Q-92
CH
N
—O—
1
8



Q-93
CH
N
—O—
1
9



Q-94
CH
N
—O—
2
7



Q-95
CH
N
—O—
2
8



Q-96
CH
N
—O—
2
9



Q-97
CH
N
—O—
3
7



Q-98
CH
N
—O—
3
8



Q-99
CH
N
—O—
3
9



Q-100
CH
N
—O—
4
7



Q-101
CH
N
—O—
4
8



Q-102
CH
N
—O—
4
9



Q-103
CH
N
—O—
5
7



Q-104
CH
N
—O—
5
8



Q-105
CH
N
—O—
5
9



Q-106
CH
N
—CH2O—
1
7



Q-107
CH
N
—CH2O—
1
8



Q-108
CH
N
—CH2O—
1
9



Q-109
CH
N
—CH2O—
2
7



Q-110
CH
N
—CH2O—
2
8























TABLE 59






Compound








No.
G1
G2
Q1
n
m








Q-111
CH
N
—CH2O—
2
9



Q-112
CH
N
—CH2O—
3
7



Q-113
CH
N
—CH2O—
3
8



Q-114
CH
N
—CH2O—
3
9



Q-115
CH
N
—CH2O—
4
7



Q-116
CH
N
—CH2O—
4
8



Q-117
CH
N
—CH2O—
4
9



Q-118
CH
N
—CH2O—
5
7



Q-119
CH
N
—CH2O—
5
8



Q-120
CH
N
—CH2O—
5
9



Q-121
CH
N
singlebond
1
7



Q-122
CH
N
singlebond
1
8



Q-123
CH
N
singlebond
1
9



Q-124
CH
N
singlebond
2
7



Q-125
CH
N
singlebond
2
8



Q-126
CH
N
singlebond
2
9



Q-127
CH
N
singlebond
3
7



Q-128
CH
N
singlebond
3
8



Q-129
CH
N
singlebond
3
9



Q-130
CH
N
singlebond
4
7



Q-131
CH
N
singlebond
4
8



Q-132
CH
N
singlebond
4
9



Q-133
CH
N
singlebond
5
7



Q-134
CH
N
singlebond
5
8



Q-135
CH
N
singlebond
5
9











embedded image

















TABLE 60





Compound










No.
G1
G2
Q1
Ra
Rb
Rc
n
m







R-1
CH
CH
—O—
Me
H
H
1
7


R-2
CH
CH
—O—
Me
H
H
1
8


R-3
CH
CH
—O—
Me
H
H
1
9


R-4
CH
CH
—O—
Me
H
H
2
7


R-5
CH
CH
—O—
Me
H
H
2
8


R-6
CH
CH
—O—
Me
H
H
2
9


R-7
CH
CH
—O—
Me
H
H
3
7


R-8
CH
CH
—O—
Me
H
H
3
8


R-9
CH
CH
—O—
Me
H
H
3
9


R-10
CH
CH
—O—
Me
H
H
4
7


R-11
CH
CH
—O—
Me
H
H
4
8


R-12
CH
CH
—O—
Me
H
H
4
9


R-13
CH
CH
—O—
Me
H
H
5
7


R-14
CH
CH
—O—
Me
H
H
5
8


R-15
CH
CH
—O—
Me
H
H
5
9


R-16
CH
CH
—O—
H
H
Me
1
7


R-17
CH
CH
—O—
H
H
Me
1
8


R-18
CH
CH
—O—
H
H
Me
1
9


R-19
CH
CH
—O—
H
H
Me
2
7


R-20
CH
CH
—O—
H
H
Me
2
8


R-21
CH
CH
—O—
H
H
Me
2
9


R-22
CH
CH
—O—
H
H
Me
3
7


R-23
CH
CH
—O—
H
H
Me
3
8


R-24
CH
CH
—O—
H
H
Me
3
9


R-25
CH
CH
—O—
H
H
Me
4
7


R-26
CH
CH
—O—
H
H
Me
4
8


R-27
CH
CH
—O—
H
H
Me
4
9


R-28
CH
CH
—O—
H
H
Me
5
7


R-29
CH
CH
—O—
H
H
Me
5
8


R-30
CH
CH
—O—
H
H
Me
5
9


R-31
CH
CH
—O—
Me
Me
H
1
7


R-32
CH
CH
—O—
Me
Me
H
1
8


R-33
CH
CH
—O—
Me
Me
H
1
9


R-34
CH
CH
—O—
Me
Me
H
2
7


R-35
CH
CH
—O—
Me
Me
H
2
8


R-36
CH
CH
—O—
Me
Me
H
2
9


R-37
CH
CH
—O—
Me
Me
H
3
7


R-38
CH
CH
—O—
Me
Me
H
3
8


R-39
CH
CH
—O—
Me
Me
H
3
9


R-40
CH
CH
—O—
Me
Me
H
4
7


R-41
CH
CH
—O—
Me
Me
H
4
8


R-42
CH
CH
—O—
Me
Me
H
4
9


R-43
CH
CH
—O—
Me
Me
H
5
7


R-44
CH
CH
—O—
Me
Me
H
5
8


R-45
CH
CH
—O—
Me
Me
H
5
9


R-46
CH
CH
—O—
H
Me
Me
1
7


R-47
CH
CH
—O—
H
Me
Me
1
8


R-48
CH
CH
—O—
H
Me
Me
1
9


R-49
CH
CH
—O—
H
Me
Me
2
7


R-50
CH
CH
—O—
H
Me
Me
2
8


R-51
CH
CH
—O—
H
Me
Me
2
9


R-52
CH
CH
—O—
H
Me
Me
3
7


R-53
CH
CH
—O—
H
Me
Me
3
8


R-54
CH
CH
—O—
H
Me
Me
3
9


R-55
CH
CH
—O—
H
Me
Me
4
7


R-56
CH
CH
—O—
H
Me
Me
4
8


R-57
CH
CH
—O—
H
Me
Me
4
9


R-58
CH
CH
—O—
H
Me
Me
5
7


R-59
CH
CH
—O—
H
Me
Me
5
8


R-60
CH
CH
—O—
H
Me
Me
5
9


R-61
CH
CH
—CH2O—
Me
H
H
1
7


R-62
CH
CH
—CH2O—
Me
H
H
1
8


R-63
CH
CH
—CH2O—
Me
H
H
1
9


R-64
CH
CH
—CH2O—
Me
H
H
2
7


R-65
CH
CH
—CH2O—
Me
H
H
2
8


R-66
CH
CH
—CH2O—
Me
H
H
2
9


R-67
CH
CH
—CH2O—
Me
H
H
3
7


R-68
CH
CH
—CH2O—
Me
H
H
3
8


R-69
CH
CH
—CH2O—
Me
H
H
3
9


R-70
CH
CH
—CH2O—
Me
H
H
4
7


R-71
CH
CH
—CH2O—
Me
H
H
4
8


R-72
CH
CH
—CH2O—
Me
H
H
4
9


R-73
CH
CH
—CH2O—
Me
H
H
5
7


R-74
CH
CH
—CH2O—
Me
H
H
5
8


R-75
CH
CH
—CH2O—
Me
H
H
5
9


R-76
CH
CH
—CH2O—
H
H
Me
1
7


R-77
CH
CH
—CH2O—
H
H
Me
1
8


R-78
CH
CH
—CH2O—
H
H
Me
1
9


R-79
CH
CH
—CH2O—
H
H
Me
2
7


R-80
CH
CH
—CH2O—
H
H
Me
2
8


R-81
CH
CH
—CH2O—
H
H
Me
2
9


R-82
CH
CH
—CH2O—
H
H
Me
3
7


R-83
CH
CH
—CH2O—
H
H
Me
3
8


R-84
CH
CH
—CH2O—
H
H
Me
3
9


R-85
CH
CH
—CH2O—
H
H
Me
4
7


R-86
CH
CH
—CH2O—
H
H
Me
4
8


R-87
CH
CH
—CH2O—
H
H
Me
4
9


R-88
CH
CH
—CH2O—
H
H
Me
5
7


R-89
CH
CH
—CH2O—
H
H
Me
5
8


R-90
CH
CH
—CH2O—
H
H
Me
5
9


R-91
CH
CH
—CH2O—
Me
Me
H
1
7


R-92
CH
CH
—CH2O—
Me
Me
H
1
8


R-93
CH
CH
—CH2O—
Me
Me
H
1
9


R-94
CH
CH
—CH2O—
Me
Me
H
2
7


R-95
CH
CH
—CH2O—
Me
Me
H
2
8


R-96
CH
CH
—CH2O—
Me
Me
H
2
9


R-97
CH
CH
—CH2O—
Me
Me
H
3
7


R-98
CH
CH
—CH2O—
Me
Me
H
3
8


R-99
CH
CH
—CH2O—
Me
Me
H
3
9


R-100
CH
CH
—CH2O—
Me
Me
H
4
7


R-101
CH
CH
—CH2O—
Me
Me
H
4
8


R-102
CH
CH
—CH2O—
Me
Me
H
4
9


R-103
CH
CH
—CH2O—
Me
Me
H
5
7


R-104
CH
CH
—CH2O—
Me
Me
H
5
8


R-105
CH
CH
—CH2O—
Me
Me
H
5
9


R-106
CH
CH
—CH2O—
H
Me
Me
1
7


R-107
CH
CH
—CH2O—
H
Me
Me
1
8


R-108
CH
CH
—CH2O—
H
Me
Me
1
9


R-109
CH
CH
—CH2O—
H
Me
Me
2
7


R-110
CH
CH
—CH2O—
H
Me
Me
2
8
























TABLE 61





Compound










No.
G1
G2
Q1
Ra
Rb
Rc
n
m







R-111
CH
CH
—CH2O—
H
Me
Me
2
9


R-112
CH
CH
—CH2O—
H
Me
Me
3
7


R-113
CH
CH
—CH2O—
H
Me
Me
3
8


R-114
CH
CH
—CH2O—
H
Me
Me
3
9


R-115
CH
CH
—CH2O—
H
Me
Me
4
7


R-116
CH
CH
—CH2O—
H
Me
Me
4
8


R-117
CH
CH
—CH2O—
H
Me
Me
4
9


R-118
CH
CH
—CH2O—
H
Me
Me
5
7


R-119
CH
CH
—CH2O—
H
Me
Me
5
8


R-120
CH
CH
—CH2O—
H
Me
Me
5
9


R-121
CH
CH
singlebond
Me
H
H
1
7


R-122
CH
CH
singlebond
Me
H
H
1
8


R-123
CH
CH
singlebond
Me
H
H
1
9


R-124
CH
CH
singlebond
Me
H
H
2
7


R-125
CH
CH
singlebond
Me
H
H
2
8


R-126
CH
CH
singlebond
Me
H
H
2
9


R-127
CH
CH
singlebond
Me
H
H
3
7


R-128
CH
CH
singlebond
Me
H
H
3
8


R-129
CH
CH
singlebond
Me
H
H
3
9


R-130
CH
CH
singlebond
Me
H
H
4
7


R-131
CH
CH
singlebond
Me
H
H
4
8


R-132
CH
CH
singlebond
Me
H
H
4
9


R-133
CH
CH
singlebond
Me
H
H
5
7


R-134
CH
CH
singlebond
Me
H
H
5
8


R-135
CH
CH
singlebond
Me
H
H
5
9


R-136
CH
CH
singlebond
H
H
Me
1
7


R-137
CH
CH
singlebond
H
H
Me
1
8


R-138
CH
CH
singlebond
H
H
Me
1
9


R-139
CH
CH
singlebond
H
H
Me
2
7


R-140
CH
CH
singlebond
H
H
Me
2
8


R-141
CH
CH
singlebond
H
H
Me
2
9


R-142
CH
CH
singlebond
H
H
Me
3
7


R-143
CH
CH
singlebond
H
H
Me
3
8


R-144
CH
CH
singlebond
H
H
Me
3
9


R-145
CH
CH
singlebond
H
H
Me
4
7


R-146
CH
CH
singlebond
H
H
Me
4
8


R-147
CH
CH
singlebond
H
H
Me
4
9


R-148
CH
CH
singlebond
H
H
Me
5
7


R-149
CH
CH
singlebond
H
H
Me
5
8


R-150
CH
CH
singlebond
H
H
Me
5
9


R-151
CH
CH
singlebond
Me
Me
H
1
7


R-152
CH
CH
singlebond
Me
Me
H
1
8


R-153
CH
CH
singlebond
Me
Me
H
1
9


R-154
CH
CH
singlebond
Me
Me
H
2
7


R-155
CH
CH
singlebond
Me
Me
H
2
8


R-156
CH
CH
singlebond
Me
Me
H
2
9


R-157
CH
CH
singlebond
Me
Me
H
3
7


R-158
CH
CH
singlebond
Me
Me
H
3
8


R-159
CH
CH
singlebond
Me
Me
H
3
9


R-160
CH
CH
singlebond
Me
Me
H
4
7


R-161
CH
CH
singlebond
Me
Me
H
4
8


R-162
CH
CH
singlebond
Me
Me
H
4
9


R-163
CH
CH
singlebond
Me
Me
H
5
7


R-164
CH
CH
singlebond
Me
Me
H
5
8


R-165
CH
CH
singlebond
Me
Me
H
5
9


R-166
CH
CH
singlebond
H
Me
Me
1
7


R-167
CH
CH
singlebond
H
Me
Me
1
8


R-168
CH
CH
singlebond
H
Me
Me
1
9


R-169
CH
CH
singlebond
H
Me
Me
2
7


R-170
CH
CH
singlebond
H
Me
Me
2
8


R-171
CH
CH
singlebond
H
Me
Me
2
9


R-172
CH
CH
singlebond
H
Me
Me
3
7


R-173
CH
CH
singlebond
H
Me
Me
3
8


R-174
CH
CH
singlebond
H
Me
Me
3
9


R-175
CH
CH
singlebond
H
Me
Me
4
7


R-176
CH
CH
singlebond
H
Me
Me
4
8


R-177
CH
CH
singlebond
H
Me
Me
4
9


R-178
CH
CH
singlebond
H
Me
Me
5
7


R-179
CH
CH
singlebond
H
Me
Me
5
8


R-180
CH
CH
singlebond
H
Me
Me
5
9


R-181
N
CH
—O—
Me
H
H
1
7


R-182
N
CH
—O—
Me
H
H
1
8


R-183
N
CH
—O—
Me
H
H
1
9


R-184
N
CH
—O—
Me
H
H
2
7


R-185
N
CH
—O—
Me
H
H
2
8


R-186
N
CH
—O—
Me
H
H
2
9


R-187
N
CH
—O—
Me
H
H
3
7


R-188
N
CH
—O—
Me
H
H
3
8


R-189
N
CH
—O—
Me
H
H
3
9


R-190
N
CH
—O—
Me
H
H
4
7


R-191
N
CH
—O—
Me
H
H
4
8


R-192
N
CH
—O—
Me
H
H
4
9


R-193
N
CH
—O—
Me
H
H
5
7


R-194
N
CH
—O—
Me
H
H
5
8


R-195
N
CH
—O—
Me
H
H
5
9


R-196
N
CH
—O—
H
H
Me
1
7


R-197
N
CH
—O—
H
H
Me
1
8


R-198
N
CH
—O—
H
H
Me
1
9


R-199
N
CH
—O—
H
H
Me
2
7


R-200
N
CH
—O—
H
H
Me
2
8


R-201
N
CH
—O—
H
H
Me
2
9


R-202
N
CH
—O—
H
H
Me
3
7


R-203
N
CH
—O—
H
H
Me
3
8


R-204
N
CH
—O—
H
H
Me
3
9


R-205
N
CH
—O—
H
H
Me
4
7


R-206
N
CH
—O—
H
H
Me
4
8


R-207
N
CH
—O—
H
H
Me
4
9


R-208
N
CH
—O—
H
H
Me
5
7


R-209
N
CH
—O—
H
H
Me
5
8


R-210
N
CH
—O—
H
H
Me
5
9


R-211
N
CH
—O—
Me
Me
H
1
7


R-212
N
CH
—O—
Me
Me
H
1
8


R-213
N
CH
—O—
Me
Me
H
1
9


R-214
N
CH
—O—
Me
Me
H
2
7


R-215
N
CH
—O—
Me
Me
H
2
8


R-216
N
CH
—O—
Me
Me
H
2
9


R-217
N
CH
—O—
Me
Me
H
3
7


R-218
N
CH
—O—
Me
Me
H
3
8


R-219
N
CH
—O—
Me
Me
H
3
9


R-220
N
CH
—O—
Me
Me
H
4
7
























TABLE 62





Compound










No.
G1
G2
Q1
Ra
Rb
Rc
n
m







R-221
N
CH
—O—
Me
Me
H
4
8


R-222
N
CH
—O—
Me
Me
H
4
9


R-223
N
CH
—O—
Me
Me
H
5
7


R-224
N
CH
—O—
Me
Me
H
5
8


R-225
N
CH
—O—
Me
Me
H
5
9


R-226
N
CH
—O—
H
Me
Me
1
7


R-227
N
CH
—O—
H
Me
Me
1
8


R-228
N
CH
—O—
H
Me
Me
1
9


R-229
N
CH
—O—
H
Me
Me
2
7


R-230
N
CH
—O—
H
Me
Me
2
8


R-231
N
CH
—O—
H
Me
Me
2
9


R-232
N
CH
—O—
H
Me
Me
3
7


R-233
N
CH
—O—
H
Me
Me
3
8


R-234
N
CH
—O—
H
Me
Me
3
9


R-235
N
CH
—O—
H
Me
Me
4
7


R-236
N
CH
—O—
H
Me
Me
4
8


R-237
N
CH
—O—
H
Me
Me
4
9


R-238
N
CH
—O—
H
Me
Me
5
7


R-239
N
CH
—O—
H
Me
Me
5
8


R-240
N
CH
—O—
H
Me
Me
5
9


R-241
N
CH
—CH2O—
Me
H
H
1
7


R-242
N
CH
—CH2O—
Me
H
H
1
8


R-243
N
CH
—CH2O—
Me
H
H
1
9


R-244
N
CH
—CH2O—
Me
H
H
2
7


R-245
N
CH
—CH2O—
Me
H
H
2
8


R-246
N
CH
—CH2O—
Me
H
H
2
9


R-247
N
CH
—CH2O—
Me
H
H
3
7


R-248
N
CH
—CH2O—
Me
H
H
3
8


R-249
N
CH
—CH2O—
Me
H
H
3
9


R-250
N
CH
—CH2O—
Me
H
H
4
7


R-251
N
CH
—CH2O—
Me
H
H
4
8


R-252
N
CH
—CH2O—
Me
H
H
4
9


R-253
N
CH
—CH2O—
Me
H
H
5
7


R-254
N
CH
—CH2O—
Me
H
H
5
8


R-255
N
CH
—CH2O—
Me
H
H
5
9


R-256
N
CH
—CH2O—
H
H
Me
1
7


R-257
N
CH
—CH2O—
H
H
Me
1
8


R-258
N
CH
—CH2O—
H
H
Me
1
9


R-259
N
CH
—CH2O—
H
H
Me
2
7


R-260
N
CH
—CH2O—
H
H
Me
2
8


R-261
N
CH
—CH2O—
H
H
Me
2
9


R-262
N
CH
—CH2O—
H
H
Me
3
7


R-263
N
CH
—CH2O—
H
H
Me
3
8


R-264
N
CH
—CH2O—
H
H
Me
3
9


R-265
N
CH
—CH2O—
H
H
Me
4
7


R-266
N
CH
—CH2O—
H
H
Me
4
8


R-267
N
CH
—CH2O—
H
H
Me
4
9


R-268
N
CH
—CH2O—
H
H
Me
5
7


R-269
N
CH
—CH2O—
H
H
Me
5
8


R-270
N
CH
—CH2O—
H
H
Me
5
9


R-271
N
CH
—CH2O—
Me
Me
H
1
7


R-272
N
CH
—CH2O—
Me
Me
H
1
8


R-273
N
CH
—CH2O—
Me
Me
H
1
9


R-274
N
CH
—CH2O—
Me
Me
H
2
7


R-275
N
CH
—CH2O—
Me
Me
H
2
8


R-276
N
CH
—CH2O—
Me
Me
H
2
9


R-277
N
CH
—CH2O—
Me
Me
H
3
7


R-278
N
CH
—CH2O—
Me
Me
H
3
8


R-279
N
CH
—CH2O—
Me
Me
H
3
9


R-280
N
CH
—CH2O—
Me
Me
H
4
7


R-281
N
CH
—CH2O—
Me
Me
H
4
8


R-282
N
CH
—CH2O—
Me
Me
H
4
9


R-283
N
CH
—CH2O—
Me
Me
H
5
7


R-284
N
CH
—CH2O—
Me
Me
H
5
8


R-285
N
CH
—CH2O—
Me
Me
H
5
9


R-286
N
CH
—CH2O—
H
Me
Me
1
7


R-287
N
CH
—CH2O—
H
Me
Me
1
8


R-288
N
CH
—CH2O—
H
Me
Me
1
9


R-289
N
CH
—CH2O—
H
Me
Me
2
7


R-290
N
CH
—CH2O—
H
Me
Me
2
8


R-291
N
CH
—CH2O—
H
Me
Me
2
9


R-292
N
CH
—CH2O—
H
Me
Me
3
7


R-293
N
CH
—CH2O—
H
Me
Me
3
8


R-294
N
CH
—CH2O—
H
Me
Me
3
9


R-295
N
CH
—CH2O—
H
Me
Me
4
7


R-296
N
CH
—CH2O—
H
Me
Me
4
8


R-297
N
CH
—CH2O—
H
Me
Me
4
9


R-298
N
CH
—CH2O—
H
Me
Me
5
7


R-299
N
CH
—CH2O—
H
Me
Me
5
8


R-300
N
CH
—CH2O—
H
Me
Me
5
9


R-301
N
CH
singlebond
Me
H
H
1
7


R-302
N
CH
singlebond
Me
H
H
1
8


R-303
N
CH
singlebond
Me
H
H
1
9


R-304
N
CH
singlebond
Me
H
H
2
7


R-305
N
CH
singlebond
Me
H
H
2
8


R-306
N
CH
singlebond
Me
H
H
2
9


R-307
N
CH
singlebond
Me
H
H
3
7


R-308
N
CH
singlebond
Me
H
H
3
8


R-309
N
CH
singlebond
Me
H
H
3
9


R-310
N
CH
singlebond
Me
H
H
4
7


R-311
N
CH
singlebond
Me
H
H
4
8


R-312
N
CH
singlebond
Me
H
H
4
9


R-313
N
CH
singlebond
Me
H
H
5
7


R-314
N
CH
singlebond
Me
H
H
5
8


R-315
N
CH
singlebond
Me
H
H
5
9


R-316
N
CH
singlebond
H
H
Me
1
7


R-317
N
CH
singlebond
H
H
Me
1
8


R-318
N
CH
singlebond
H
H
Me
1
9


R-319
N
CH
singlebond
H
H
Me
2
7


R-320
N
CH
singlebond
H
H
Me
2
8


R-321
N
CH
singlebond
H
H
Me
2
9


R-322
N
CH
singlebond
H
H
Me
3
7


R-323
N
CH
singlebond
H
H
Me
3
8


R-324
N
CH
singlebond
H
H
Me
3
9


R-325
N
CH
singlebond
H
H
Me
4
7


R-326
N
CH
singlebond
H
H
Me
4
8


R-327
N
CH
singlebond
H
H
Me
4
9


R-323
N
CH
singlebond
H
H
Me
5
7


R-329
N
CH
singlebond
H
H
Me
5
8


R-330
N
CH
singlebond
H
H
Me
5
9
























TABLE 63





Compound










No.
G1
G2
Q1
Ra
Rb
Rc
n
m







R-331
N
CH
singlebond
Me
Me
H
1
7


R-332
N
CH
singlebond
Me
Me
H
1
8


R-333
N
CH
singlebond
Me
Me
H
1
9


R-334
N
CH
singlebond
Me
Me
H
2
7


R-335
N
CH
singlebond
Me
Me
H
2
8


R-336
N
CH
singlebond
Me
Me
H
2
9


R-337
N
CH
singlebond
Me
Me
H
3
7


R-338
N
CH
singlebond
Me
Me
H
3
8


R-339
N
CH
singlebond
Me
Me
H
3
9


R-340
N
CH
singlebond
Me
Me
H
4
7


R-341
N
CH
singlebond
Me
Me
H
4
8


R-342
N
CH
singlebond
Me
Me
H
4
9


R-343
N
CH
singlebond
Me
Me
H
5
7


R-344
N
CH
singlebond
Me
Me
H
5
8


R-345
N
CH
singlebond
Me
Me
H
5
9


R-346
N
CH
singlebond
H
Me
Me
1
7


R-347
N
CH
singlebond
H
Me
Me
1
8


R-348
N
CH
singlebond
H
Me
Me
1
9


R-349
N
CH
singlebond
H
Me
Me
2
7


R-350
N
CH
singlebond
H
Me
Me
2
8


R-351
N
CH
singlebond
H
Me
Me
2
9


R-352
N
CH
singlebond
H
Me
Me
3
7


R-353
N
CH
singlebond
H
Me
Me
3
8


R-354
N
CH
singlebond
H
Me
Me
3
9


R-355
N
CH
singlebond
H
Me
Me
4
7


R-356
N
CH
singlebond
H
Me
Me
4
8


R-357
N
CH
singlebond
H
Me
Me
4
9


R-358
N
CH
singlebond
H
Me
Me
5
7


R-359
N
CH
singlebond
H
Me
Me
5
8


R-360
N
CH
singlebond
H
Me
Me
5
9


R-361
CH
N
—O—
Me
H
H
1
7


R-362
CH
N
—O—
Me
H
H
1
8


R-363
CH
N
—O—
Me
H
H
1
9


R-364
CH
N
—O—
Me
H
H
2
7


R-365
CH
N
—O—
Me
H
H
2
8


R-366
CH
N
—O—
Me
H
H
2
9


R-367
CH
N
—O—
Me
H
H
3
7


R-368
CH
N
—O—
Me
H
H
3
8


R-369
CH
N
—O—
Me
H
H
3
9


R-370
CH
N
—O—
Me
H
H
4
7


R-371
CH
N
—O—
Me
H
H
4
8


R-372
CH
N
—O—
Me
H
H
4
9


R-373
CH
N
—O—
Me
H
H
5
7


R-374
CH
N
—O—
Me
H
H
5
8


R-375
CH
N
—O—
Me
H
H
5
9


R-376
CH
N
—O—
H
H
Me
1
7


R-377
CH
N
—O—
H
H
Me
1
8


R-378
CH
N
—O—
H
H
Me
1
9


R-379
CH
N
—O—
H
H
Me
2
7


R-380
CH
N
—O—
H
H
Me
2
8


R-381
CH
N
—O—
H
H
Me
2
9


R-382
CH
N
—O—
H
H
Me
3
7


R-383
CH
N
—O—
H
H
Me
3
8


R-384
CH
N
—O—
H
H
Me
3
9


R-385
CH
N
—O—
H
H
Me
4
7


R-386
CH
N
—O—
H
H
Me
4
8


R-387
CH
N
—O—
H
H
Me
4
9


R-388
CH
N
—O—
H
H
Me
5
7


R-389
CH
N
—O—
H
H
Me
5
8


R-390
CH
N
—O—
H
H
Me
5
9


R-391
CH
N
—O—
Me
Me
H
1
7


R-392
CH
N
—O—
Me
Me
H
1
8


R-393
CH
N
—O—
Me
Me
H
1
9


R-394
CH
N
—O—
Me
Me
H
2
7


R-395
CH
N
—O—
Me
Me
H
2
8


R-396
CH
N
—O—
Me
Me
H
2
9


R-397
CH
N
—O—
Me
Me
H
3
7


R-398
CH
N
—O—
Me
Me
H
3
8


R-399
CH
N
—O—
Me
Me
H
3
9


R-400
CH
N
—O—
Me
Me
H
4
7


R-401
CH
N
—O—
Me
Me
H
4
8


R-402
CH
N
—O—
Me
Me
H
4
9


R-403
CH
N
—O—
Me
Me
H
5
7


R-404
CH
N
—O—
Me
Me
H
5
8


R-405
CH
N
—O—
Me
Me
H
5
9


R-406
CH
N
—O—
H
Me
Me
1
7


R-407
CH
N
—O—
H
Me
Me
1
8


R-408
CH
N
—O—
H
Me
Me
1
9


R-409
CH
N
—O—
H
Me
Me
2
7


R-410
CH
N
—O—
H
Me
Me
2
8


R-411
CH
N
—O—
H
Me
Me
2
9


R-412
CH
N
—O—
H
Me
Me
3
7


R-413
CH
N
—O—
H
Me
Me
3
8


R-414
CH
N
—O—
H
Me
Me
3
9


R-415
CH
N
—O—
H
Me
Me
4
7


R-416
CH
N
—O—
H
Me
Me
4
8


R-417
CH
N
—O—
H
Me
Me
4
9


R-418
CH
N
—O—
H
Me
Me
5
7


R-419
CH
N
—O—
H
Me
Me
5
8


R-420
CH
N
—O—
H
Me
Me
5
9


R-421
CH
N
—CH2O—
Me
H
H
1
7


R-422
CH
N
—CH2O—
Me
H
H
1
8


R-423
CH
N
—CH2O—
Me
H
H
1
9


R-424
CH
N
—CH2O—
Me
H
H
2
7


R-425
CH
N
—CH2O—
Me
H
H
2
8


R-426
CH
N
—CH2O—
Me
H
H
2
9


R-427
CH
N
—CH2O—
Me
H
H
3
7


R-428
CH
N
—CH2O—
Me
H
H
3
8


R-429
CH
N
—CH2O—
Me
H
H
3
9


R-430
CH
N
—CH2O—
Me
H
H
4
7


R-431
CH
N
—CH2O—
Me
H
H
4
8


R-432
CH
N
—CH2O—
Me
H
H
4
9


R-433
CH
N
—CH2O—
Me
H
H
5
7


R-434
CH
N
—CH2O—
Me
H
H
5
8


R-435
CH
N
—CH2O—
Me
H
H
5
9


R-436
CH
N
—CH2O—
H
H
Me
1
7


R-437
CH
N
—CH2O—
H
H
Me
1
8


R-438
CH
N
—CH2O—
H
H
Me
1
9


R-439
CH
N
—CH2O—
H
H
Me
2
7


R-440
CH
N
—CH2O—
H
H
Me
2
8
























TABLE 64





Compound










No.
G1
G2
Q1
Ra
Rb
Rc
n
m







R-441
CH
N
—CH2O—
H
H
Me
2
9


R-442
CH
N
—CH2O—
H
H
Me
3
7


R-443
CH
N
—CH2O—
H
H
Me
3
8


R-444
CH
N
—CH2O—
H
H
Me
3
9


R-445
CH
N
—CH2O—
H
H
Me
4
7


R-446
CH
N
—CH2O—
H
H
Me
4
8


R-447
CH
N
—CH2O—
H
H
Me
4
9


R-448
CH
N
—CH2O—
H
H
Me
5
7


R-449
CH
N
—CH2O—
H
H
Me
5
8


R-450
CH
N
—CH2O—
H
H
Me
5
9


R-451
CH
N
—CH2O—
Me
Me
H
1
7


R-452
CH
N
—CH2O—
Me
Me
H
1
8


R-453
CH
N
—CH2O—
Me
Me
H
1
9


R-454
CH
N
—CH2O—
Me
Me
H
2
7


R-455
CH
N
—CH2O—
Me
Me
H
2
8


R-456
CH
N
—CH2O—
Me
Me
H
2
9


R-457
CH
N
—CH2O—
Me
Me
H
3
7


R-458
CH
N
—CH2O—
Me
Me
H
3
8


R-459
CH
N
—CH2O—
Me
Me
H
3
9


R-460
CH
N
—CH2O—
Me
Me
H
4
7


R-461
CH
N
—CH2O—
Me
Me
H
4
8


R-462
CH
N
—CH2O—
Me
Me
H
4
9


R-463
CH
N
—CH2O—
Me
Me
H
5
7


R-464
CH
N
—CH2O—
Me
Me
H
5
8


R-465
CH
N
—CH2O—
Me
Me
H
5
9


R-466
CH
N
—CH2O—
H
Me
Me
1
7


R-467
CH
N
—CH2O—
H
Me
Me
1
8


R-468
CH
N
—CH2O—
H
Me
Me
1
9


R-469
CH
N
—CH2O—
H
Me
Me
2
7


R-470
CH
N
—CH2O—
H
Me
Me
2
8


R-471
CH
N
—CH2O—
H
Me
Me
2
9


R-472
CH
N
—CH2O—
H
Me
Me
3
7


R-473
CH
N
—CH2O—
H
Me
Me
3
8


R-474
CH
N
—CH2O—
H
Me
Me
3
9


R-475
CH
N
—CH2O—
H
Me
Me
4
7


R-476
CH
N
—CH2O—
H
Me
Me
4
8


R-477
CH
N
—CH2O—
H
Me
Me
4
9


R-478
CH
N
—CH2O—
H
Me
Me
5
7


R-479
CH
N
—CH2O—
H
Me
Me
5
8


R-480
CH
N
—CH2O—
H
Me
Me
5
9


R-481
CH
N
singlebond
Me
H
H
1
7


R-482
CH
N
singlebond
Me
H
H
1
8


R-483
CH
N
singlebond
Me
H
H
1
9


R-484
CH
N
singlebond
Me
H
H
2
7


R-485
CH
N
singlebond
Me
H
H
2
8


R-486
CH
N
singlebond
Me
H
H
2
9


R-487
CH
N
singlebond
Me
H
H
3
7


R-488
CH
N
singlebond
Me
H
H
3
8


R-489
CH
N
singlebond
Me
H
H
3
9


R-490
CH
N
singlebond
Me
H
H
4
7


R-491
CH
N
singlebond
Me
H
H
4
8


R-492
CH
N
singlebond
Me
H
H
4
9


R-493
CH
N
singlebond
Me
H
H
5
7


R-494
CH
N
singlebond
Me
H
H
5
8


R-495
CH
N
singlebond
Me
H
H
5
9


R-496
CH
N
singlebond
H
H
Me
1
7


R-497
CH
N
singlebond
H
H
Me
1
8


R-498
CH
N
singlebond
H
H
Me
1
9


R-499
CH
N
singlebond
H
H
Me
2
7


R-500
CH
N
singlebond
H
H
Me
2
8


R-501
CH
N
singlebond
H
H
Me
2
9


R-502
CH
N
singlebond
H
H
Me
3
7


R-503
CH
N
singlebond
H
H
Me
3
8


R-504
CH
N
singlebond
H
H
Me
3
9


R-505
CH
N
singlebond
H
H
Me
4
7


R-506
CH
N
singlebond
H
H
Me
4
8


R-507
CH
N
singlebond
H
H
Me
4
9


R-508
CH
N
singlebond
H
H
Me
5
7


R-509
CH
N
singlebond
H
H
Me
5
8


R-510
CH
N
singlebond
H
H
Me
5
9


R-511
CH
N
singlebond
Me
Me
H
1
7


R-512
CH
N
singlebond
Me
Me
H
1
8


R-513
CH
N
singlebond
Me
Me
H
1
9


R-514
CH
N
singlebond
Me
Me
H
2
7


R-515
CH
N
singlebond
Me
Me
H
2
8


R-516
CH
N
singlebond
Me
Me
H
2
9


R-517
CH
N
singlebond
Me
Me
H
3
7


R-518
CH
N
singlebond
Me
Me
H
3
8


R-519
CH
N
singlebond
Me
Me
H
3
9


R-520
CH
N
singlebond
Me
Me
H
4
7


R-521
CH
N
singlebond
Me
Me
H
4
8


R-522
CH
N
singlebond
Me
Me
H
4
9


R-523
CH
N
singlebond
Me
Me
H
5
7


R-524
CH
N
singlebond
Me
Me
H
5
8


R-525
CH
N
singlebond
Me
Me
H
5
9


R-526
CH
N
singlebond
H
Me
Me
1
7


R-527
CH
N
singlebond
H
Me
Me
1
8


R-528
CH
N
singlebond
H
Me
Me
1
9


R-529
CH
N
singlebond
H
Me
Me
2
7


R-530
CH
N
singlebond
H
Me
Me
2
8


R-531
CH
N
singlebond
H
Me
Me
2
9


R-532
CH
N
singlebond
H
Me
Me
3
7


R-533
CH
N
singlebond
H
Me
Me
3
8


R-534
CH
N
singlebond
H
Me
Me
3
9


R-535
CH
N
singlebond
H
Me
Me
4
7


R-536
CH
N
singlebond
H
Me
Me
4
8


R-537
CH
N
singlebond
H
Me
Me
4
9


R-538
CH
N
singlebond
H
Me
Me
5
7


R-539
CH
N
singlebond
H
Me
Me
5
8


R-540
CH
N
singlebond
H
Me
Me
5
9











embedded image

















TABLE 65





Compound










No.
G1
G2
Q1
Ra
Rb
Rc
n
m







S-1
CH
CH
—O—
Me
H
H
1
7


S-2
CH
CH
—O—
Me
H
H
1
8


S-3
CH
CH
—O—
Me
H
H
1
9


S-4
CH
CH
—O—
Me
H
H
2
7


S-5
CH
CH
—O—
Me
H
H
2
8


S-6
CH
CH
—O—
Me
H
H
2
9


S-7
CH
CH
—O—
Me
H
H
3
7


S-8
CH
CH
—O—
Me
H
H
3
8


S-9
CH
CH
—O—
Me
H
H
3
9


S-10
CH
CH
—O—
Me
H
H
4
7


S-11
CH
CH
—O—
Me
H
H
4
8


S-12
CH
CH
—O—
Me
H
H
4
9


S-13
CH
CH
—O—
Me
H
H
5
7


S-14
CH
CH
—O—
Me
H
H
5
8


S-15
CH
CH
—O—
Me
H
H
5
9


S-16
CH
CH
—O—
H
H
Me
1
7


S-17
CH
CH
—O—
H
H
Me
1
8


S-18
CH
CH
—O—
H
H
Me
1
9


S-19
CH
CH
—O—
H
H
Me
2
7


S-20
CH
CH
—O—
H
H
Me
2
8


S-21
CH
CH
—O—
H
H
Me
2
9


S-22
CH
CH
—O—
H
H
Me
3
7


S-23
CH
CH
—O—
H
H
Me
3
8


S-24
CH
CH
—O—
H
H
Me
3
9


S-25
CH
CH
—O—
H
H
Me
4
7


S-26
CH
CH
—O—
H
H
Me
4
8


S-27
CH
CH
—O—
H
H
Me
4
9


S-28
CH
CH
—O—
H
H
Me
5
7


S-29
CH
CH
—O—
H
H
Me
5
8


S-30
CH
CH
—O—
H
H
Me
5
9


S-31
CH
CH
—O—
Me
Me
H
1
7


S-32
CH
CH
—O—
Me
Me
H
1
8


S-33
CH
CH
—O—
Me
Me
H
1
9


S-34
CH
CH
—O—
Me
Me
H
2
7


S-35
CH
CH
—O—
Me
Me
H
2
8


S-36
CH
CH
—O—
Me
Me
H
2
9


S-37
CH
CH
—O—
Me
Me
H
3
7


S-38
CH
CH
—O—
Me
Me
H
3
8


S-39
CH
CH
—O—
Me
Me
H
3
9


S-40
CH
CH
—O—
Me
Me
H
4
7


S-41
CH
CH
—O—
Me
Me
H
4
8


S-42
CH
CH
—O—
Me
Me
H
4
9


S-43
CH
CH
—O—
Me
Me
H
5
7


S-44
CH
CH
—O—
Me
Me
H
5
8


S-45
CH
CH
—O—
Me
Me
H
5
9


S-46
CH
CH
—O—
H
Me
Me
1
7


S-47
CH
CH
—O—
H
Me
Me
1
8


S-48
CH
CH
—O—
H
Me
Me
1
9


S-49
CH
CH
—O—
H
Me
Me
2
7


S-50
CH
CH
—O—
H
Me
Me
2
8


S-51
CH
CH
—O—
H
Me
Me
2
9


S-52
CH
CH
—O—
H
Me
Me
3
7


S-53
CH
CH
—O—
H
Me
Me
3
8


S-54
CH
CH
—O—
H
Me
Me
3
9


S-55
CH
CH
—O—
H
Me
Me
4
7


S-56
CH
CH
—O—
H
Me
Me
4
8


S-57
CH
CH
—O—
H
Me
Me
4
9


S-58
CH
CH
—O—
H
Me
Me
5
7


S-59
CH
CH
—O—
H
Me
Me
5
8


S-60
CH
CH
—O—
H
Me
Me
5
9


S-61
CH
CH
—CH2O—
Me
H
H
1
7


S-62
CH
CH
—CH2O—
Me
H
H
1
8


S-63
CH
CH
—CH2O—
Me
H
H
1
9


S-64
CH
CH
—CH2O—
Me
H
H
2
7


S-65
CH
CH
—CH2O—
Me
H
H
2
8


S-66
CH
CH
—CH2O—
Me
H
H
2
9


S-67
CH
CH
—CH2O—
Me
H
H
3
7


S-68
CH
CH
—CH2O—
Me
H
H
3
8


S-69
CH
CH
—CH2O—
Me
H
H
3
9


S-70
CH
CH
—CH2O—
Me
H
H
4
7


S-71
CH
CH
—CH2O—
Me
H
H
4
8


S-72
CH
CH
—CH2O—
Me
H
H
4
9


S-73
CH
CH
—CH2O—
Me
H
H
5
7


S-74
CH
CH
—CH2O—
Me
H
H
5
8


S-75
CH
CH
—CH2O—
Me
H
H
5
9


S-76
CH
CH
—CH2O—
H
H
Me
1
7


S-77
CH
CH
—CH2O—
H
H
Me
1
8


S-78
CH
CH
—CH2O—
H
H
Me
1
9


S-79
CH
CH
—CH2O—
H
H
Me
2
7


S-80
CH
CH
—CH2O—
H
H
Me
2
8


S-81
CH
CH
—CH2O—
H
H
Me
2
9


S-82
CH
CH
—CH2O—
H
H
Me
3
7


S-83
CH
CH
—CH2O—
H
H
Me
3
8


S-84
CH
CH
—CH2O—
H
H
Me
3
9


S-85
CH
CH
—CH2O—
H
H
Me
4
7


S-86
CH
CH
—CH2O—
H
H
Me
4
8


S-87
CH
CH
—CH2O—
H
H
Me
4
9


S-88
CH
CH
—CH2O—
H
H
Me
5
7


S-89
CH
CH
—CH2O—
H
H
Me
5
8


S-90
CH
CH
—CH2O—
H
H
Me
5
9


S-91
CH
CH
—CH2O—
Me
Me
H
1
7


S-92
CH
CH
—CH2O—
Me
Me
H
1
8


S-93
CH
CH
—CH2O—
Me
Me
H
1
9


S-94
CH
CH
—CH2O—
Me
Me
H
2
7


S-95
CH
CH
—CH2O—
Me
Me
H
2
8


S-96
CH
CH
—CH2O—
Me
Me
H
2
9


S-97
CH
CH
—CH2O—
Me
Me
H
3
7


S-98
CH
CH
—CH2O—
Me
Me
H
3
8


S-99
CH
CH
—CH2O—
Me
Me
H
3
9


S-100
CH
CH
—CH2O—
Me
Me
H
4
7


S-101
CH
CH
—CH2O—
Me
Me
H
4
8


S-102
CH
CH
—CH2O—
Me
Me
H
4
9


S-103
CH
CH
—CH2O—
Me
Me
H
5
7


S-104
CH
CH
—CH2O—
Me
Me
H
5
8


S-105
CH
CH
—CH2O—
Me
Me
H
5
9


S-106
CH
CH
—CH2O—
H
Me
Me
1
7


S-107
CH
CH
—CH2O—
H
Me
Me
1
8


S-108
CH
CH
—CH2O—
H
Me
Me
1
9


S-109
CH
CH
—CH2O—
H
Me
Me
2
7


S-110
CH
CH
—CH2O—
H
Me
Me
2
8
























TABLE 66





Compound










No.
G1
G2
Q1
Ra
Rb
Rc
n
m







S-111
CH
CH
—CH2O—
H
Me
Me
2
9


S-112
CH
CH
—CH2O—
H
Me
Me
3
7


S-113
CH
CH
—CH2O—
H
Me
Me
3
8


S-114
CH
CH
—CH2O—
H
Me
Me
3
9


S-115
CH
CH
—CH2O—
H
Me
Me
4
7


S-116
CH
CH
—CH2O—
H
Me
Me
4
8


S-117
CH
CH
—CH2O—
H
Me
Me
4
9


S-118
CH
CH
—CH2O—
H
Me
Me
5
7


S-119
CH
CH
—CH2O—
H
Me
Me
5
8


S-120
CH
CH
—CH2O—
H
Me
Me
5
9


S-121
CH
CH
singlebond
Me
H
H
1
7


S-122
CH
CH
singlebond
Me
H
H
1
8


S-123
CH
CH
singlebond
Me
H
H
1
9


S-124
CH
CH
singlebond
Me
H
H
2
7


S-125
CH
CH
singlebond
Me
H
H
2
8


S-126
CH
CH
singlebond
Me
H
H
2
9


S-127
CH
CH
singlebond
Me
H
H
3
7


S-128
CH
CH
singlebond
Me
H
H
3
8


S-129
CH
CH
singlebond
Me
H
H
3
9


S-130
CH
CH
singlebond
Me
H
H
4
7


S-131
CH
CH
singlebond
Me
H
H
4
8


S-132
CH
CH
singlebond
Me
H
H
4
9


S-133
CH
CH
singlebond
Me
H
H
5
7


S-134
CH
CH
singlebond
Me
H
H
5
8


S-135
CH
CH
singlebond
Me
H
H
5
9


S-136
CH
CH
singlebond
H
H
Me
1
7


S-137
CH
CH
singlebond
H
H
Me
1
8


S-138
CH
CH
singlebond
H
H
Me
1
9


S-139
CH
CH
singlebond
H
H
Me
2
7


S-140
CH
CH
singlebond
H
H
Me
2
8


S-141
CH
CH
singlebond
H
H
Me
2
9


S-142
CH
CH
singlebond
H
H
Me
3
7


S-143
CH
CH
singlebond
H
H
Me
3
8


S-144
CH
CH
singlebond
H
H
Me
3
9


S-145
CH
CH
singlebond
H
H
Me
4
7


S-146
CH
CH
singlebond
H
H
Me
4
8


S-147
CH
CH
singlebond
H
H
Me
4
9


S-148
CH
CH
singlebond
H
H
Me
5
7


S-149
CH
CH
singlebond
H
H
Me
5
8


S-150
CH
CH
singlebond
H
H
Me
5
9


S-151
CH
CH
singlebond
Me
Me
H
1
7


S-152
CH
CH
singlebond
Me
Me
H
1
8


S-153
CH
CH
singlebond
Me
Me
H
1
9


S-154
CH
CH
singlebond
Me
Me
H
2
7


S-155
CH
CH
singlebond
Me
Me
H
2
8


S-156
CH
CH
singlebond
Me
Me
H
2
9


S-157
CH
CH
singlebond
Me
Me
H
3
7


S-158
CH
CH
singlebond
Me
Me
H
3
8


S-159
CH
CH
singlebond
Me
Me
H
3
9


S-160
CH
CH
singlebond
Me
Me
H
4
7


S-161
CH
CH
singlebond
Me
Me
H
4
8


S-162
CH
CH
singlebond
Me
Me
H
4
9


S-163
CH
CH
singlebond
Me
Me
H
5
7


S-164
CH
CH
singlebond
Me
Me
H
5
8


S-165
CH
CH
singlebond
Me
Me
H
5
9


S-166
CH
CH
singlebond
H
Me
Me
1
7


S-167
CH
CH
singlebond
H
Me
Me
1
8


S-168
CH
CH
singlebond
H
Me
Me
1
9


S-169
CH
CH
singlebond
H
Me
Me
2
7


S-170
CH
CH
singlebond
H
Me
Me
2
8


S-171
CH
CH
singlebond
H
Me
Me
2
9


S-172
CH
CH
singlebond
H
Me
Me
3
7


S-173
CH
CH
singlebond
H
Me
Me
3
8


S-174
CH
CH
singlebond
H
Me
Me
3
9


S-175
CH
CH
singlebond
H
Me
Me
4
7


S-176
CH
CH
singlebond
H
Me
Me
4
8


S-177
CH
CH
singlebond
H
Me
Me
4
9


S-178
CH
CH
singlebond
H
Me
Me
5
7


S-179
CH
CH
singlebond
H
Me
Me
5
8


S-180
CH
CH
singlebond
H
Me
Me
5
9


S-181
N
CH
—O—
Me
H
H
1
7


S-182
N
CH
—O—
Me
H
H
1
8


S-183
N
CH
—O—
Me
H
H
1
9


S-184
N
CH
—O—
Me
H
H
2
7


S-185
N
CH
—O—
Me
H
H
2
8


S-186
N
CH
—O—
Me
H
H
2
9


S-187
N
CH
—O—
Me
H
H
3
7


S-188
N
CH
—O—
Me
H
H
3
8


S-189
N
CH
—O—
Me
H
H
3
9


S-190
N
CH
—O—
Me
H
H
4
7


S-191
N
CH
—O—
Me
H
H
4
8


S-192
N
CH
—O—
Me
H
H
4
9


S-193
N
CH
—O—
Me
H
H
5
7


S-194
N
CH
—O—
Me
H
H
5
8


S-195
N
CH
—O—
Me
H
H
5
9


S-196
N
CH
—O—
H
H
Me
1
7


S-197
N
CH
—O—
H
H
Me
1
8


S-198
N
CH
—O—
H
H
Me
1
9


S-199
N
CH
—O—
H
H
Me
2
7


S-200
N
CH
—O—
H
H
Me
2
8


S-201
N
CH
—O—
H
H
Me
2
9


S-202
N
CH
—O—
H
H
Me
3
7


S-203
N
CH
—O—
H
H
Me
3
8


S-204
N
CH
—O—
H
H
Me
3
9


S-205
N
CH
—O—
H
H
Me
4
7


S-206
N
CH
—O—
H
H
Me
4
8


S-207
N
CH
—O—
H
H
Me
4
9


S-208
N
CH
—O—
H
H
Me
5
7


S-209
N
CH
—O—
H
H
Me
5
8


S-210
N
CH
—O—
H
H
Me
5
9


S-211
N
CH
—O—
Me
Me
H
1
7


S-212
N
CH
—O—
Me
Me
H
1
8


S-213
N
CH
—O—
Me
Me
H
1
9


S-214
N
CH
—O—
Me
Me
H
2
7


S-215
N
CH
—O—
Me
Me
H
2
8


S-216
N
CH
—O—
Me
Me
H
2
9


S-217
N
CH
—O—
Me
Me
H
3
7


S-218
N
CH
—O—
Me
Me
H
3
8


S-219
N
CH
—O—
Me
Me
H
3
9


S-220
N
CH
—O—
Me
Me
H
4
7
























TABLE 67





Compound










No.
G1
G2
Q1
Ra
Rb
Rc
n
m







S-221
N
CH
—O—
Me
Me
H
4
8


S-222
N
CH
—O—
Me
Me
H
4
9


S-223
N
CH
—O—
Me
Me
H
5
7


S-224
N
CH
—O—
Me
Me
H
5
8


S-225
N
CH
—O—
Me
Me
H
5
9


S-226
N
CH
—O—
H
Me
Me
1
7


S-227
N
CH
—O—
H
Me
Me
1
8


S-228
N
CH
—O—
H
Me
Me
1
9


S-229
N
CH
—O—
H
Me
Me
2
7


S-230
N
CH
—O—
H
Me
Me
2
8


S-231
N
CH
—O—
H
Me
Me
2
9


S-232
N
CH
—O—
H
Me
Me
3
7


S-233
N
CH
—O—
H
Me
Me
3
8


S-234
N
CH
—O—
H
Me
Me
3
9


S-235
N
CH
—O—
H
Me
Me
4
7


S-236
N
CH
—O—
H
Me
Me
4
8


S-237
N
CH
—O—
H
Me
Me
4
9


S-238
N
CH
—O—
H
Me
Me
5
7


S-239
N
CH
—O—
H
Me
Me
5
8


S-240
N
CH
—O—
H
Me
Me
5
9


S-241
N
CH
—CH2O—
Me
H
H
1
7


S-242
N
CH
—CH2O—
Me
H
H
1
8


S-243
N
CH
—CH2O—
Me
H
H
1
9


S-244
N
CH
—CH2O—
Me
H
H
2
7


S-245
N
CH
—CH2O—
Me
H
H
2
8


S-246
N
CH
—CH2O—
Me
H
H
2
9


S-247
N
CH
—CH2O—
Me
H
H
3
7


S-248
N
CH
—CH2O—
Me
H
H
3
8


S-249
N
CH
—CH2O—
Me
H
H
3
9


S-250
N
CH
—CH2O—
Me
H
H
4
7


S-251
N
CH
—CH2O—
Me
H
H
4
8


S-252
N
CH
—CH2O—
Me
H
H
4
9


S-253
N
CH
—CH2O—
Me
H
H
5
7


S-254
N
CH
—CH2O—
Me
H
H
5
8


S-255
N
CH
—CH2O—
Me
H
H
5
9


S-256
N
CH
—CH2O—
H
H
Me
1
7


S-257
N
CH
—CH2O—
H
H
Me
1
8


S-258
N
CH
—CH2O—
H
H
Me
1
9


S-259
N
CH
—CH2O—
H
H
Me
2
7


S-260
N
CH
—CH2O—
H
H
Me
2
8


S-261
N
CH
—CH2O—
H
H
Me
2
9


S-262
N
CH
—CH2O—
H
H
Me
3
7


S-263
N
CH
—CH2O—
H
H
Me
3
8


S-264
N
CH
—CH2O—
H
H
Me
3
9


S-265
N
CH
—CH2O—
H
H
Me
4
7


S-266
N
CH
—CH2O—
H
H
Me
4
8


S-267
N
CH
—CH2O—
H
H
Me
4
9


S-268
N
CH
—CH2O—
H
H
Me
5
7


S-269
N
CH
—CH2O—
H
H
Me
5
8


S-270
N
CH
—CH2O—
H
H
Me
5
9


S-271
N
CH
—CH2O—
Me
Me
H
1
7


S-272
N
CH
—CH2O—
Me
Me
H
1
8


S-273
N
CH
—CH2O—
Me
Me
H
1
9


S-274
N
CH
—CH2O—
Me
Me
H
2
7


S-275
N
CH
—CH2O—
Me
Me
H
2
8


S-276
N
CH
—CH2O—
Me
Me
H
2
9


S-277
N
CH
—CH2O—
Me
Me
H
3
7


S-278
N
CH
—CH2O—
Me
Me
H
3
8


S-279
N
CH
—CH2O—
Me
Me
H
3
9


S-280
N
CH
—CH2O—
Me
Me
H
4
7


S-281
N
CH
—CH2O—
Me
Me
H
4
8


S-282
N
CH
—CH2O—
Me
Me
H
4
9


S-283
N
CH
—CH2O—
Me
Me
H
5
7


S-284
N
CH
—CH2O—
Me
Me
H
5
8


S-285
N
CH
—CH2O—
Me
Me
H
5
9


S-286
N
CH
—CH2O—
H
Me
Me
1
7


S-287
N
CH
—CH2O—
H
Me
Me
1
8


S-288
N
CH
—CH2O—
H
Me
Me
1
9


S-289
N
CH
—CH2O—
H
Me
Me
2
7


S-290
N
CH
—CH2O—
H
Me
Me
2
8


S-291
N
CH
—CH2O—
H
Me
Me
2
9


S-292
N
CH
—CH2O—
H
Me
Me
3
7


S-293
N
CH
—CH2O—
H
Me
Me
3
8


S-294
N
CH
—CH2O—
H
Me
Me
3
9


S-295
N
CH
—CH2O—
H
Me
Me
4
7


S-296
N
CH
—CH2O—
H
Me
Me
4
8


S-297
N
CH
—CH2O—
H
Me
Me
4
9


S-298
N
CH
—CH2O—
H
Me
Me
5
7


S-299
N
CH
—CH2O—
H
Me
Me
5
8


S-300
N
CH
—CH2O—
H
Me
Me
5
9


S-301
N
CH
singlebond
Me
H
H
1
7


S-302
N
CH
singlebond
Me
H
H
1
8


S-303
N
CH
singlebond
Me
H
H
1
9


S-304
N
CH
singlebond
Me
H
H
2
7


S-305
N
CH
singlebond
Me
H
H
2
8


S-306
N
CH
singlebond
Me
H
H
2
9


S-307
N
CH
singlebond
Me
H
H
3
7


S-308
N
CH
singlebond
Me
H
H
3
8


S-309
N
CH
singlebond
Me
H
H
3
9


S-310
N
CH
singlebond
Me
H
H
4
7


S-311
N
CH
singlebond
Me
H
H
4
8


S-312
N
CH
singlebond
Me
H
H
4
9


S-313
N
CH
singlebond
Me
H
H
5
7


S-314
N
CH
singlebond
Me
H
H
5
8


S-315
N
CH
singlebond
Me
H
H
5
9


S-316
N
CH
singlebond
H
H
Me
1
7


S-317
N
CH
singlebond
H
H
Me
1
8


S-318
N
CH
singlebond
H
H
Me
1
9


S-319
N
CH
singlebond
H
H
Me
2
7


S-320
N
CH
singlebond
H
H
Me
2
8


S-321
N
CH
singlebond
H
H
Me
2
9


S-322
N
CH
singlebond
H
H
Me
3
7


S-323
N
CH
singlebond
H
H
Me
3
8


S-324
N
CH
singlebond
H
H
Me
3
9


S-325
N
CH
singlebond
H
H
Me
4
7


S-326
N
CH
singlebond
H
H
Me
4
8


S-327
N
CH
singlebond
H
H
Me
4
9


S-328
N
CH
singlebond
H
H
Me
5
7


S-329
N
CH
singlebond
H
H
Me
5
8


S-330
N
CH
singlebond
H
H
Me
5
9
























TABLE 68





Compound










No.
G1
G2
Q1
Ra
Rb
Rc
n
m







S-331
N
CH
singlebond
Me
Me
H
1
7


S-332
N
CH
singlebond
Me
Me
H
1
8


S-333
N
CH
singlebond
Me
Me
H
1
9


S-334
N
CH
singlebond
Me
Me
H
2
7


S-335
N
CH
singlebond
Me
Me
H
2
8


S-336
N
CH
singlebond
Me
Me
H
2
9


S-337
N
CH
singlebond
Me
Me
H
3
7


S-338
N
CH
singlebond
Me
Me
H
3
8


S-339
N
CH
singlebond
Me
Me
H
3
9


S-340
N
CH
singlebond
Me
Me
H
4
7


S-341
N
CH
singlebond
Me
Me
H
4
8


S-342
N
CH
singlebond
Me
Me
H
4
9


S-343
N
CH
singlebond
Me
Me
H
5
7


S-344
N
CH
singlebond
Me
Me
H
5
8


S-345
N
CH
singlebond
Me
Me
H
5
9


S-346
N
CH
singlebond
H
Me
Me
1
7


S-347
N
CH
singlebond
H
Me
Me
1
8


S-348
N
CH
singlebond
H
Me
Me
1
9


S-349
N
CH
singlebond
H
Me
Me
2
7


S-350
N
CH
singlebond
H
Me
Me
2
8


S-351
N
CH
singlebond
H
Me
Me
2
9


S-352
N
CH
singlebond
H
Me
Me
3
7


S-353
N
CH
singlebond
H
Me
Me
3
8


S-354
N
CH
singlebond
H
Me
Me
3
9


S-355
N
CH
singlebond
H
Me
Me
4
7


S-356
N
CH
singlebond
H
Me
Me
4
8


S-357
N
CH
singlebond
H
Me
Me
4
9


S-358
N
CH
singlebond
H
Me
Me
5
7


S-359
N
CH
singlebond
H
Me
Me
5
8


S-360
N
CH
singlebond
H
Me
Me
5
9


S-361
CH
N
—O—
Me
H
H
1
7


S-362
CH
N
—O—
Me
H
H
1
8


S-363
CH
N
—O—
Me
H
H
1
9


S-364
CH
N
—O—
Me
H
H
2
7


S-365
CH
N
—O—
Me
H
H
2
8


S-366
CH
N
—O—
Me
H
H
2
9


S-367
CH
N
—O—
Me
H
H
3
7


S-368
CH
N
—O—
Me
H
H
3
8


S-369
CH
N
—O—
Me
H
H
3
9


S-370
CH
N
—O—
Me
H
H
4
7


S-371
CH
N
—O—
Me
H
H
4
8


S-372
CH
N
—O—
Me
H
H
4
9


S-373
CH
N
—O—
Me
H
H
5
7


S-374
CH
N
—O—
Me
H
H
5
8


S-375
CH
N
—O—
Me
H
H
5
9


S-376
CH
N
—O—
H
H
Me
1
7


S-377
CH
N
—O—
H
H
Me
1
8


S-378
CH
N
—O—
H
H
Me
1
9


S-379
CH
N
—O—
H
H
Me
2
7


S-380
CH
N
—O—
H
H
Me
2
8


S-381
CH
N
—O—
H
H
Me
2
9


S-382
CH
N
—O—
H
H
Me
3
7


S-383
CH
N
—O—
H
H
Me
3
8


S-384
CH
N
—O—
H
H
Me
3
9


S-385
CH
N
—O—
H
H
Me
4
7


S-386
CH
N
—O—
H
H
Me
4
8


S-387
CH
N
—O—
H
H
Me
4
9


S-388
CH
N
—O—
H
H
Me
5
7


S-389
CH
N
—O—
H
H
Me
5
8


S-390
CH
N
—O—
H
H
Me
5
9


S-391
CH
N
—O—
Me
Me
H
1
7


S-392
CH
N
—O—
Me
Me
H
1
8


S-393
CH
N
—O—
Me
Me
H
1
9


S-394
CH
N
—O—
Me
Me
H
2
7


S-395
CH
N
—O—
Me
Me
H
2
8


S-396
CH
N
—O—
Me
Me
H
2
9


S-397
CH
N
—O—
Me
Me
H
3
7


S-398
CH
N
—O—
Me
Me
H
3
8


S-399
CH
N
—O—
Me
Me
H
3
9


S-400
CH
N
—O—
Me
Me
H
4
7


S-401
CH
N
—O—
Me
Me
H
4
8


S-402
CH
N
—O—
Me
Me
H
4
9


S-403
CH
N
—O—
Me
Me
H
5
7


S-404
CH
N
—O—
Me
Me
H
5
8


S-405
CH
N
—O—
Me
Me
H
5
9


S-406
CH
N
—O—
H
Me
Me
1
7


S-407
CH
N
—O—
H
Me
Me
1
8


S-408
CH
N
—O—
H
Me
Me
1
9


S-409
CH
N
—O—
H
Me
Me
2
7


S-410
CH
N
—O—
H
Me
Me
2
8


S-411
CH
N
—O—
H
Me
Me
2
9


S-412
CH
N
—O—
H
Me
Me
3
7


S-413
CH
N
—O—
H
Me
Me
3
8


S-414
CH
N
—O—
H
Me
Me
3
9


S-415
CH
N
—O—
H
Me
Me
4
7


S-416
CH
N
—O—
H
Me
Me
4
8


S-417
CH
N
—O—
H
Me
Me
4
9


S-418
CH
N
—O—
H
Me
Me
5
7


S-419
CH
N
—O—
H
Me
Me
5
8


S-420
CH
N
—O—
H
Me
Me
5
9


S-421
CH
N
—CH2O—
Me
H
H
1
7


S-422
CH
N
—CH2O—
Me
H
H
1
8


S-423
CH
N
—CH2O—
Me
H
H
1
9


S-424
CH
N
—CH2O—
Me
H
H
2
7


S-425
CH
N
—CH2O—
Me
H
H
2
8


S-426
CH
N
—CH2O—
Me
H
H
2
9


5-427
CH
N
—CH2O—
Me
H
H
3
7


S-428
CH
N
—CH2O—
Me
H
H
3
8


S-429
CH
N
—CH2O—
Me
H
H
3
9


S-430
CH
N
—CH2O—
Me
H
H
4
7


S-431
CH
N
—CH2O—
Me
H
H
4
8


S-432
CH
N
—CH2O—
Me
H
H
4
9


S-433
CH
N
—CH2O—
Me
H
H
5
7


S-434
CH
N
—CH2O—
Me
H
H
5
8


S-435
CH
N
—CH2O—
Me
H
H
5
9


S-436
CH
N
—CH2O—
H
H
Me
1
7


S-437
CH
N
—CH2O—
H
H
Me
1
8


S-438
CH
N
—CH2O—
H
H
Me
1
9


S-439
CH
N
—CH2O—
H
H
Me
2
7


S-440
CH
N
—CH2O—
H
H
Me
2
8
























TABLE 69





Compound










No.
G1
G2
Q1
Ra
Rb
Rc
n
m







S-441
CH
N
—CH2O—
H
H
Me
2
9


S-442
CH
N
—CH2O—
H
H
Me
3
7


S-443
CH
N
—CH2O—
H
H
Me
3
8


S-444
CH
N
—CH2O—
H
H
Me
3
9


S-445
CH
N
—CH2O—
H
H
Me
4
7


S-446
CH
N
—CH2O—
H
H
Me
4
8


S-447
CH
N
—CH2O—
H
H
Me
4
9


S-448
CH
N
—CH2O—
H
H
Me
5
7


S-449
CH
N
—CH2O—
H
H
Me
5
8


S-450
CH
N
—CH2O—
H
H
Me
5
9


S-451
CH
N
—CH2O—
Me
Me
H
1
7


S-452
CH
N
—CH2O—
Me
Me
H
1
8


S-453
CH
N
—CH2O—
Me
Me
H
1
9


S-454
CH
N
—CH2O—
Me
Me
H
2
7


S-455
CH
N
—CH2O—
Me
Me
H
2
8


S-456
CH
N
—CH2O—
Me
Me
H
2
9


S-457
CH
N
—CH2O—
Me
Me
H
3
7


S-458
CH
N
—CH2O—
Me
Me
H
3
8


S-459
CH
N
—CH2O—
Me
Me
H
3
9


S-460
CH
N
—CH2O—
Me
Me
H
4
7


S-461
CH
N
—CH2O—
Me
Me
H
4
8


S-462
CH
N
—CH2O—
Me
Me
H
4
9


S-463
CH
N
—CH2O—
Me
Me
H
5
7


S-464
CH
N
—CH2O—
Me
Me
H
5
8


S-465
CH
N
—CH2O—
Me
Me
H
5
9


S-466
CH
N
—CH2O—
H
Me
Me
1
7


S-467
CH
N
—CH2O—
H
Me
Me
1
8


S-468
CH
N
—CH2O—
H
Me
Me
1
9


S-469
CH
N
—CH2O—
H
Me
Me
2
7


S-470
CH
N
—CH2O—
H
Me
Me
2
8


S-471
CH
N
—CH2O—
H
Me
Me
2
9


S-472
CH
N
—CH2O—
H
Me
Me
3
7


S-473
CH
N
—CH2O—
H
Me
Me
3
8


S-474
CH
N
—CH2O—
H
Me
Me
3
9


S-475
CH
N
—CH2O—
H
Me
Me
4
7


S-476
CH
N
—CH2O—
H
Me
Me
4
8


S-477
CH
N
—CH2O—
H
Me
Me
4
9


S-478
CH
N
—CH2O—
H
Me
Me
5
7


S-479
CH
N
—CH2O—
H
Me
Me
5
8


S-480
CH
N
—CH2O—
H
Me
Me
5
9


S-481
CH
N
singlebond
Me
H
H
1
7


S-482
CH
N
singlebond
Me
H
H
1
8


S-483
CH
N
singlebond
Me
H
H
1
9


S-484
CH
N
singlebond
Me
H
H
2
7


S-485
CH
N
singlebond
Me
H
H
2
8


S-486
CH
N
singlebond
Me
H
H
2
9


S-487
CH
N
singlebond
Me
H
H
3
7


S-488
CH
N
singlebond
Me
H
H
3
8


S-489
CH
N
singlebond
Me
H
H
3
9


S-490
CH
N
singlebond
Me
H
H
4
7


S-491
CH
N
singlebond
Me
H
H
4
8


S-492
CH
N
singlebond
Me
H
H
4
9


S-493
CH
N
singlebond
Me
H
H
5
7


S-494
CH
N
singlebond
Me
H
H
5
8


S-495
CH
N
singlebond
Me
H
H
5
9


S-496
CH
N
singlebond
H
H
Me
1
7


S-497
CH
N
singlebond
H
H
Me
1
8


S-498
CH
N
singlebond
H
H
Me
1
9


S-499
CH
N
singlebond
H
H
Me
2
7


S-500
CH
N
singlebond
H
H
Me
2
8


S-501
CH
N
singlebond
H
H
Me
2
9


S-502
CH
N
singlebond
H
H
Me
3
7


S-503
CH
N
singlebond
H
H
Me
3
8


S-504
CH
N
singlebond
H
H
Me
3
9


S-505
CH
N
singlebond
H
H
Me
4
7


S-506
CH
N
singlebond
H
H
Me
4
8


S-507
CH
N
singlebond
H
H
Me
4
9


S-508
CH
N
singlebond
H
H
Me
5
7


S-509
CH
N
singlebond
H
H
Me
5
8


S-510
CH
N
singlebond
H
H
Me
5
9


S-511
CH
N
singlebond
Me
Me
H
1
7


S-512
CH
N
singlebond
Me
Me
H
1
8


S-513
CH
N
singlebond
Me
Me
H
1
9


S-514
CH
N
singlebond
Me
Me
H
2
7


S-515
CH
N
singlebond
Me
Me
H
2
8


S-516
CH
N
singlebond
Me
Me
H
2
9


S-517
CH
N
singlebond
Me
Me
H
3
7


S-518
CH
N
singlebond
Me
Me
H
3
8


S-519
CH
N
singlebond
Me
Me
H
3
9


S-520
CH
N
singlebond
Me
Me
H
4
7


S-521
CH
N
singlebond
Me
Me
H
4
8


S-522
CH
N
singlebond
Me
Me
H
4
9


S-523
CH
N
singlebond
Me
Me
H
5
7


S-524
CH
N
singlebond
Me
Me
H
5
8


S-525
CH
N
singlebond
Me
Me
H
5
9


S-526
CH
N
singlebond
H
Me
Me
1
7


S-527
CH
N
singlebond
H
Me
Me
1
8


S-528
CH
N
singlebond
H
Me
Me
1
9


S-529
CH
N
singlebond
H
Me
Me
2
7


S-530
CH
N
singlebond
H
Me
Me
2
8


S-531
CH
N
singlebond
H
Me
Me
2
9


S-532
CH
N
singlebond
H
Me
Me
3
7


S-533
CH
N
singlebond
H
Me
Me
3
8


S-534
CH
N
singlebond
H
Me
Me
3
9


S-535
CH
N
singlebond
H
Me
Me
4
7


S-536
CH
N
singlebond
H
Me
Me
4
8


S-537
CH
N
singlebond
H
Me
Me
4
9


S-538
CH
N
singlebond
H
Me
Me
5
7


S-539
CH
N
singlebond
H
Me
Me
5
8


S-540
CH
N
singlebond
H
Me
Me
5
9











embedded image















TABLE 70






Compound








No.
G1
G2
Q1
n
m








T-1
CH
CH
—O—
1
7



T-2
CH
CH
—O—
1
8



T-3
CH
CH
—O—
1
9



T-4
CH
CH
—O—
2
7



T-5
CH
CH
—O—
2
8



T-6
CH
CH
—O—
2
9



T-7
CH
CH
—O—
3
7



T-8
CH
CH
—O—
3
8



T-9
CH
CH
—O—
3
9



T-10
CH
CH
—O—
4
7



T-11
CH
CH
—O—
4
8



T-12
CH
CH
—O—
4
9



T-13
CH
CH
—O—
5
7



T-14
CH
CH
—O—
5
8



T-15
CH
CH
—O—
5
9



T-16
CH
CH
—CH2O—
1
7



T-17
CH
CH
—CH2O—
1
8



T-18
CH
CH
—CH2O—
1
9



T-19
CH
CH
—CH2O—
2
7



T-20
CH
CH
—CH2O—
2
8



T-21
CH
CH
—CH2O—
2
9



T-22
CH
CH
—CH2O—
3
7



T-23
CH
CH
—CH2O—
3
8



T-24
CH
CH
—CH2O—
3
9



T-25
CH
CH
—CH2O—
4
7



T-26
CH
CH
—CH2O—
4
8



T-27
CH
CH
—CH2O—
4
9



T-28
CH
CH
—CH2O—
5
7



T-29
CH
CH
—CH2O—
5
8



T-30
CH
CH
—CH2O—
5
9



T-31
CH
CH
singlebond
1
7



T-32
CH
CH
singlebond
1
8



T-33
CH
CH
singlebond
1
9



T-34
CH
CH
singlebond
2
7



T-35
CH
CH
singlebond
2
8



T-36
CH
CH
singlebond
2
9



T-37
CH
CH
singlebond
3
7



T-38
CH
CH
singlebond
3
8



T-39
CH
CH
singlebond
3
9



T-40
CH
CH
singlebond
4
7



T-41
CH
CH
singlebond
4
8



T-42
CH
CH
singlebond
4
9



T-43
CH
CH
singlebond
5
7



T-44
CH
CH
singlebond
5
8



T-45
CH
CH
singlebond
5
9



T-46
N
CH
—O—
1
7



T-47
N
CH
—O—
1
8



T-48
N
CH
—O—
1
9



T-49
N
CH
—O—
2
7



T-50
N
CH
—O—
2
8



T-51
N
CH
—O—
2
9



T-52
N
CH
—O—
3
7



T-53
N
CH
—O—
3
8



T-54
N
CH
—O—
3
9



T-55
N
CH
—O—
4
7



T-56
N
CH
—O—
4
8



T-57
N
CH
—O—
4
9



T-58
N
CH
—O—
5
7



T-59
N
CH
—O—
5
8



T-60
N
CH
—O—
5
9



T-61
N
CH
—CH2O—
1
7



T-62
N
CH
—CH2O—
1
8



T-63
N
CH
—CH2O—
1
9



T-64
N
CH
—CH2O—
2
7



T-65
N
CH
—CH2O—
2
8



T-66
N
CH
—CH2O—
2
9



T-67
N
CH
—CH2O—
3
7



T-68
N
CH
—CH2O—
3
8



T-69
N
CH
—CH2O—
3
9



T-70
N
CH
—CH2O—
4
7



T-71
N
CH
—CH2O—
4
8



T-72
N
CH
—CH2O—
4
9



T-73
N
CH
—CH2O—
5
7



T-74
N
CH
—CH2O—
5
8



T-75
N
CH
—CH2O—
5
9



T-76
N
CH
singlebond
1
7



T-77
N
CH
singlebond
1
8



T-78
N
CH
singlebond
1
9



T-79
N
CH
singlebond
2
7



T-80
N
CH
singlebond
2
8



T-81
N
CH
singlebond
2
9



T-82
N
CH
singlebond
3
7



T-83
N
CH
singlebond
3
8



T-84
N
CH
singlebond
3
9



T-85
N
CH
singlebond
4
7



T-86
N
CH
singlebond
4
8



T-87
N
CH
singlebond
4
9



T-88
N
CH
singlebond
5
7



T-89
N
CH
singlebond
5
8



T-90
N
CH
singlebond
5
9



T-91
CH
N
—O—
1
7



T-92
CH
N
—O—
1
8



T-93
CH
N
—O—
1
9



T-94
CH
N
—O—
2
7



T-95
CH
N
—O—
2
8



T-96
CH
N
—O—
2
9



T-97
CH
N
—O—
3
7



T-98
CH
N
—O—
3
8



T-99
CH
N
—O—
3
9



T-100
CH
N
—O—
4
7



T-101
CH
N
—O—
4
8



T-102
CH
N
—O—
4
9



T-103
CH
N
—O—
5
7



T-104
CH
N
—O—
5
8



T-105
CH
N
—O—
5
9



T-106
CH
N
—CH2O—
1
7



T-107
CH
N
—CH2O—
1
8



T-108
CH
N
—CH2O—
1
9



T-109
CH
N
—CH2O—
2
7



T-110
CH
N
—CH2O—
2
8






















TABLE 71






Compound








No.
G1
G2
Q1
n
m








T-111
CH
N
—CH2O—
2
9



T-112
CH
N
—CH2O—
3
7



T-113
CH
N
—CH2O—
3
8



T-114
CH
N
—CH2O—
3
9



T-115
CH
N
—CH2O—
4
7



T-116
CH
N
—CH2O—
4
8



T-117
CH
N
—CH2O—
4
9



T-118
CH
N
—CH2O—
5
7



T-119
CH
N
—CH2O—
5
8



T-120
CH
N
—CH2O—
5
9



T-121
CH
N
singlebond
1
7



T-122
CH
N
singlebond
1
8



T-123
CH
N
singlebond
1
9



T-124
CH
N
singlebond
2
7



T-125
CH
N
singlebond
2
8



T-126
CH
N
singlebond
2
9



T-127
CH
N
singlebond
3
7



T-128
CH
N
singlebond
3
8



T-129
CH
N
singlebond
3
9



T-130
CH
N
singlebond
4
7



T-131
CH
N
singlebond
4
8



T-132
CH
N
singlebond
4
9



T-133
CH
N
singlebond
5
7



T-134
CH
N
singlebond
5
8



T-135
CH
N
singlebond
5
9











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TABLE 72






Compound








No.
G1
G2
Q1
n
m








U-1
CH
CH
—O—
1
7



U-2
CH
CH
—O—
1
8



U-3
CH
CH
—O—
1
9



U-4
CH
CH
—O—
2
7



U-5
CH
CH
—O—
2
8



U-6
CH
CH
—O—
2
9



U-7
CH
CH
—O—
3
7



U-8
CH
CH
—O—
3
8



U-9
CH
CH
—O—
3
9



U-10
CH
CH
—O—
4
7



U-11
CH
CH
—O—
4
8



U-12
CH
CH
—O—
4
9



U-13
CH
CH
—O—
5
7



U-14
CH
CH
—O—
5
8



U-15
CH
CH
—O—
5
9



U-16
CH
CH
—CH2O—
1
7



U-17
CH
CH
—CH2O—
1
8



U-18
CH
CH
—CH2O—
1
9



U-19
CH
CH
—CH2O—
2
7



U-20
CH
CH
—CH2O—
2
8



U-21
CH
CH
—CH2O—
2
9



U-22
CH
CH
—CH2O—
3
7



U-23
CH
CH
—CH2O—
3
8



U-24
CH
CH
—CH2O—
3
9



U-25
CH
CH
—CH2O—
4
7



U-26
CH
CH
—CH2O—
4
8



U-27
CH
CH
—CH2O—
4
9



U-28
CH
CH
—CH2O—
5
7



U-29
CH
CH
—CH2O—
5
8



U-30
CH
CH
—CH2O—
5
9



U-31
CH
CH
singlebond
1
7



U-32
CH
CH
singlebond
1
8



U-33
CH
CH
singlebond
1
9



U-34
CH
CH
singlebond
2
7



U-35
CH
CH
singlebond
2
8



U-36
CH
CH
singlebond
2
9



U-37
CH
CH
singlebond
3
7



U-38
CH
CH
singlebond
3
8



U-39
CH
CH
singlebond
3
9



U-40
CH
CH
singlebond
4
7



U-41
CH
CH
singlebond
4
8



U-42
CH
CH
singlebond
4
9



U-43
CH
CH
singlebond
5
7



U-44
CH
CH
singlebond
5
8



U-45
CH
CH
singlebond
5
9



U-46
N
CH
—O—
1
7



U-47
N
CH
—O—
1
8



U-48
N
CH
—O—
1
9



U-49
N
CH
—O—
2
7



U-50
N
CH
—O—
2
8



U-51
N
CH
—O—
2
9



U-52
N
CH
—O—
3
7



U-53
N
CH
—O—
3
8



U-54
N
CH
—O—
3
9



U-55
N
CH
—O—
4
7



U-56
N
CH
—O—
4
8



U-57
N
CH
—O—
4
9



U-58
N
CH
—O—
5
7



U-59
N
CH
—O—
5
8



U-60
N
CH
—O—
5
9



U-61
N
CH
—CH2O—
1
7



U-62
N
CH
—CH2O—
1
8



U-63
N
CH
—CH2O—
1
9



U-64
N
CH
—CH2O—
2
7



U-65
N
CH
—CH2O—
2
8



U-66
N
CH
—CH2O—
2
9



U-67
N
CH
—CH2O—
3
7



U-68
N
CH
—CH2O—
3
8



U-69
N
CH
—CH2O—
3
9



U-70
N
CH
—CH2O—
4
7



U-71
N
CH
—CH2O—
4
8



U-72
N
CH
—CH2O—
4
9



U-73
N
CH
—CH2O—
5
7



U-74
N
CH
—CH2O—
5
8



U-75
N
CH
—CH2O—
5
9



U-76
N
CH
singlebond
1
7



U-77
N
CH
singlebond
1
8



U-78
N
CH
singlebond
1
9



U-79
N
CH
singlebond
2
7



U-80
N
CH
singlebond
2
8



U-81
N
CH
singlebond
2
9



U-82
N
CH
singlebond
3
7



U-83
N
CH
singlebond
3
8



U-84
N
CH
singlebond
3
9



U-85
N
CH
singlebond
4
7



U-86
N
CH
singlebond
4
8



U-87
N
CH
singlebond
4
9



U-88
N
CH
singlebond
5
7



U-89
N
CH
singlebond
5
8



U-90
N
CH
singlebond
5
9



U-91
CH
N
—O—
1
7



U-92
CH
N
—O—
1
8



U-93
CH
N
—O—
1
9



U-94
CH
N
—O—
2
7



U-95
CH
N
—O—
2
8



U-96
CH
N
—O—
2
9



U-97
CH
N
—O—
3
7



U-98
CH
N
—O—
3
8



U-99
CH
N
—O—
3
9



U-100
CH
N
—O—
4
7



U-101
CH
N
—O—
4
8



U-102
CH
N
—O—
4
9



U-103
CH
N
—O—
5
7



U-104
CH
N
—O—
5
8



U-105
CH
N
—O—
5
9



U-106
CH
N
—CH2O—
1
7



U-107
CH
N
—CH2O—
1
8



U-108
CH
N
—CH2O—
1
9



U-109
CH
N
—CH2O—
2
7



U-110
CH
N
—CH2O—
2
8






















TABLE 73






Compound








No.
G1
G2
Q1
n
m








U-111
CH
N
—CH2O—
2
9



U-112
CH
N
—CH2O—
3
7



U-113
CH
N
—CH2O—
3
8



U-114
CH
N
—CH2O—
3
9



U-115
CH
N
—CH2O—
4
7



U-116
CH
N
—CH2O—
4
8



U-117
CH
N
—CH2O—
4
9



U-118
CH
N
—CH2O—
5
7



U-119
CH
N
—CH2O—
5
8



U-120
CH
N
—CH2O—
5
9



U-121
CH
N
singlebond
1
7



U-122
CH
N
singlebond
1
8



U-123
CH
N
singlebond
1
9



U-124
CH
N
singlebond
2
7



U-125
CH
N
singlebond
2
8



U-126
CH
N
singlebond
2
9



U-127
CH
N
singlebond
3
7



U-128
CH
N
singlebond
3
8



U-129
CH
N
singlebond
3
9



U-130
CH
N
singlebond
4
7



U-131
CH
N
singlebond
4
8



U-132
CH
N
singlebond
4
9



U-133
CH
N
singlebond
5
7



U-134
CH
N
singlebond
5
8



U-135
CH
N
singlebond
5
9









The compound [I] according to the present invention includes hydrates, various solvates and crystal polymorphs. Furthermore, the compound [I] according to the present invention includes stereoisomers and tautomers based on an asymmetric carbon atom, a double bond, or the like, and mixtures thereof.


Salts of the compound [I] according to the present invention are not particularly limited, provided that the salts are agriculturally and horticulturally acceptable salts. Examples thereof include: salts of inorganic acid such as hydrochloric acid or sulfuric acid; salts of organic acid such as acetic acid or lactic acid; salts of alkali metal such as lithium, sodium, or potassium; salts of alkaline earth metal such as calcium or magnesium; salts of transition metal such as iron or copper; salts of organic base such as ammonia, triethylamine, tributylamine, pyridine, or hydrazine. Salts of the compound [I] may be obtained by a known method from the compound [I].


Next, production examples of the amidine compound represented by formula [I] and salts thereof will be described. The production examples shown below are intended to illustrate the present invention and are not intended to limit the scope of the present invention.


PRODUCTION EXAMPLE 1

Cyclic guanidine compound (1) and a compound (2) are reacted to obtain a compound (3). The compound (3) and a halogen compound (4) are reacted to obtain a compound (5). A guanidine derivative (6) and the compound (5) are reacted to obtain a compound (7). A protecting group P and a protective group P′ of the compound (7) are deprotected to obtain a guanidine compound (8) according to the present invention.




embedded image


In the formulae, A1, Q1, X, Z, and R51 are described above. Hal represents a halogen atom and P and P′ represent protective groups.


PRODUCTION EXAMPLE 2

An alcohol compound (9) and a guanidine derivative (10) are reacted by Mitsunobu reaction to obtain a compound (11). The compound (11) and the guanidine derivative (6) are reacted to obtain a compound (12). A protecting group P and a protective group P′ of the compound (12) are deprotected to obtain a guanidine compound (13) according to the present invention.




embedded image


In the formulae, A1, Q1, X, and Z are described above. Hal represents a halogen atom and P and P′ represent protective groups.


After a completion of the synthesis reaction, post-treatments which are ordinary conducted in organic synthetic chemistry, and, as needed, conventionally known separation and puririfaction procedures make it possible to efficiently isolate a target product.


Structure of the target product can be identified and confirmed by measurement of 1H-NMR spectrum, IR spectrum, or mass spectrum, or elemental analysis.


The fungicide or plant disease control agent according to the present invention contains at least one selected from the group consisting of the compound [I] and the salt thereof as an active component thereof. The amount of the active ingredient contained in the fungicide or plant disease control agent according to the present invention, relative to the whole formulation, is preferably 0.01 to 90% by weight, and more preferably 0.05 to 85% by weight.


The fungicide or plant disease-controlling agent according to the present invention may be used in an agrochemically acceptable form, that is, in a form of an agrochemical formulation, such as water-dispersible powder, granule, powder, emulsion, water-soluble powder, suspension, or water-dispersible granule.


Examples of an additive and a carrier used in solid formulation include: vegetable powder such as soybean flour or wheat flour; mineral fine powder such as diatomite, apatite, plaster, talc, bentonite, pyrophylite, or clay; and an organic or inorganic compound such as sodium benzoate, urea, or sulfate of soda.


Examples of a solvent used in liquid formulation include: kerosene, xylene, petroleum-based aromatic hydrocarbons, cyclohexane, cyclohexanone, dimethyl formamide, dimethyl sulfoxide, alcohol, acetone, trichloroethylene, methylisobutylketone, mineral oil, vegetable oil, and water.


In addition, a surfactant may be added to the formulation, as necessary, in order to realize a uniform and stable form.


The surfactant which may be added is not particularly limited. Examples of the surfactant include: non-ionic surfactants such as polyoxyethylene-added alkylphenylether, polyoxyethylene-added alkylether, polyoxyethylene-added higher fatty acid ester, polyoxyethylene-added sorbitan higher fatty acid ester, polyoxyethylene-added tristyrylphenylether; sulfuric ester salts of polyoxyethylene-added alkylphenylethers, alkylbenzene sulfonates, sulfuric ester salts of higher alcohol, alkylnaphthalene sulfonates, polycarboxylates, lignin sulfonates, formaldehyde condensates of alkylnaphthalene sulfonates, and isobutylene-anhydrous maleic acid copolymers.


The thus obtained water-dispersible powder, emulsion, flowable agent, water-soluble powder, or water-dispersible granules are diluted with water to a predetermined concentration and used as a solution, a suspension, or an emulsion to be sprayed onto plants. Also, the powder and the granules are used to be sprayed directly onto plants.


The fungicide or plant disease control agent according to the present invention can be used to control a variety of diseases that occur upon the cultivation of agricultural and horticultural crops, including flowers, lawns, and grass, by seed treatment, foliage application, soil application or submerged application.


Although the application amount of the fungicide or plant disease-controlling agent according to the present invention is influenced by weather conditions, formulation form, application time, application method, application place, target disease to be controlled, or target crops, an amount of an active ingredient thereof per 1 hectare is preferably 1 to 1,000 g, and more preferably 10 to 100 g.


In the case where a water-dispersible powder, emulsion, suspension, water-soluble powder, or water-dispersible granule is applied after being diluted with water, the application concentration is preferably 1 to 1,000 ppm, and more preferably 10 to 250 ppm.


The fungicide or plant disease-controlling agent according to the present invention may be used to control against plant diseases caused by a wide range of types of fungus belonging to filamentous fungi such as phycomycetes (Oomycetes), ascomycetes (sac) fungi (Ascomycetes), imperfect fungi (Deuteromycetes), basidiomycetes (Basidiomycetes), or zygomycetes (Zygomycetes).


Examples of plant diseases and pathogens to be controlled include the followings.


Sugar beet: brown spot disease (Cercospora beticola), black root disease (Aphanomyces cochlioides), root rot disease (Thanatephorus cucumeris), leaf rot disease (Thanatephorus cucumeris), and the like.


Peanut: brown spot disease (Mycosphaerella arachidis), leaf mold (Ascochyta sp.), rust disease (Puccinia arachidis), damping-off disease (Pythium debaryanum), rust spot disease (Alternaria alternate), stem rot disease (Sclerotium rolfsii), black rust disease (Mycosphaerella berkeleyi), and the like.


Cucumber: powdery mildew (Sphaerotheca fuliginea), downy mildew (Pseudoperonospora cubensis), gummy stem blight (Mycosphaerella melonis), wilt disease (Fusarium oxysporum), sclerotinia rot (Sclerotinia sclerotiorum), gray mold (Botrytis cinerea), anthracnose (Colletotrichum orbiculare), scab (Cladosporium cucumerinum), brown spot disease (Corynespora cassiicola), damping-off disease (Pythium debaryanam, Rhizoctonia solani Kuhn), Phomopsis root rot disease (Phomopsis sp.), Bacterial spot (Pseudomonas syringae pv.Lecrymans), and the like.


Tomato: gray mold disease (Botrytis cinerea), leaf mold disease (Cladosporium fulvum), late blight disease (Phytophthora infestans), verticillium wilt disease (Verticillium albo-atrum), powdery mildew disease (Oidium neolycopersici), early blight disease (Alternaria solani), leaf mold disease (Pseudocercospora fuligena), and the like.


Eggplant: gray mold disease (Botrytis cinerea), black rot disease (Corynespora melongenae), powdery mildew disease (Erysiphe cichoracearum), leaf mold disease (Mycovellosiella nattrassii), sclerotinia rot disease (Sclerotinia sclerotiorum), and the like.


Strawberry: gray mold disease (Botrytis cinerea), powdery mildew disease (Sphaerotheca humuli), anthracnose disease (Colletotrichum acutatum, Colletotrichum fragariae), phytophthora rot disease (Phytophthora cactorum), soft rot disease (Rhizopus stolonifer), fsarium wilt disease(Fusarium oxysporum), and the like.


Onion: neck rot disease (Botrytis allii), gray mold disease (Botrytis cinerea), leaf blight disease (Botrytis squamosal), downy mildew disease (Peronospora destructor), Phytophthora porri disease (Phytophthora porri), and the like.


Cabbage: clubroot disease (Plasmodiophora brassicae), soft rot disease (Erwinia carotovora), black rot disease (Xanthomonas campesrtis pv. Campestris), bacterial black spot disease (Pseudomonas syringae pv. maculicala, Pseudomonas syringae pv. Alisalensis), downy mildew disease (Peronospora parasitica), sclerotinia rot disease (Sclerotinia sclerotiorum), black spot disease (Alternaria brassicicola), gray mold disease (Botrytis cinerea), and the like.


Common bean: sclerotinia rot disease (Sclerotinia sclerotiorum), gray mold disease (Botrytis cinerea), anthracnose (Colletotrichum lindemuthianum), angular spot disease (Phaeoisariopsis griseola), and the like.


Apple: powdery mildew disease (Podosphaera leucotricha), scab disease (Venturia inaequalis), Monilinia disease (Monilinia mali), black spot disease (Mycosphaerella pomi), valsa canker disease (Valsa mali), alternaria blotch disease (Alternaria mali), rust disease (Gymnosporangium yamadae), ring rot disease (Botryosphaeria berengeriana), anthracnose disease (Glomerella cingulata, Colletotrichum acutatum), leaf srot disease (Diplocarpon mali), fly speck disease (Zygophiala jamaicensis), Sooty blotch (Gloeodes pomigena), violet root rot disease (Helicobasidium mompa), gray mold disease (Botrytis cinerea), and the like.


Japanese apricot: scab disease (Cladosporium carpophilum), gray mold disease (Botrytis cinerea), brown rot disease (Monilinia mumecola), and the like.


Persimmon: powdery mildew disease (Phyllactinia kakicola), anthracnose disease (Gloeosporium kaki), angular leaf spot (Cercospora kaki), and the like.


Peach: brown rot disease (Monilinia fructicola), scab disease (Cladosporium carpophilum), phomopsis rot disease (Phomopsis sp.), bacterial shot hole disease (Xanthomonas campestris pv. Pruni), and the like.


Almond: brown rot disease (Monilinia laxa), spot blotch disease (Stigmina carpophila), scab disease (Cladosporium carpophilum), red leaf spot disease (Polystigma rubrum), alternaria blotch disease (Alternaria alternata), anthracnose (Colletotrichum gloeospoides), and the like.


Yellow peach: brown rot disease (Monilinia fructicola), anthracnose disease (Colletotrichum acutatum), black spot disease (Alternaria sp.), Monilinia Kusanoi disease (Monilinia kusanoi), and the like.


Grape: gray mold disease (Botrytis cinerea), powdery mildew disease (Uncinula necator), ripe rot disease (Glomerella cingulata, Colletotrichum acutatum), downy mildew disease (Plasmopara viticola), anthracnose disease (Elsinoe ampelina), brown spot disease (Pseudocercospora vitis), black rot disease (Guignardia bidwellii), white rot disease (Coniella castaneicola), and the like.


Pear: scab disease (Venturia nashicola), rust disease (Gymnosporangium asiaticum), black spot disease (Alternaria kikuchiana), ring rot disease (Botryosphaeria berengeriana), powdery mildew disease (Phyllactinia mali), cytospora canker disease (Phomopsis fukushii), brown spot blotch disease (Stemphylium vesicarium), anthracnose disease (Glomerella cingulate), and the like.


Tea: ring spot disease (Pestalotia theae), anthracnose disease (Colletotrichum theae-sinensis), and the like.


Citrus fruits: scab disease (Elsinoe fawcetti), blue mold disease (Penicillium italicum), common green mold disease (Penicillium digitatum), gray mold disease (Botrytis cinerea), melanose disease (Diaporthe citri), canker disease (Xanthomonas campestris pv.Citri), powdery mildew disease (Oidium sp.), and the like.


Wheat: powdery mildew (Erysiphe graminis f.sp. Tritici), red mold disease (Gibberella zeae), red rust disease (Puccinia recondite), brown snow mold disease (Pythium iwayamai), pink snow mold disease (Monographella nivalis), eye spot disease (Pseudocercosporella herpotrichoides), leaf scorch disease (Septoria tritici), glume blotch disease (Leptosphaeria nodorum), typhulasnow blight disease (Typhula incarnate), sclerotinia snow blight disease (Myriosclerotinia borealis), damping-off disease (Gaeumanomyces graminis), ergot disease (Claviceps purpurea), stinking smut disease (Tilletia caries), loose smut disease (Ustilago nuda), and the like.


Barley: leaf spot disease (Pyrenophora graminea), net blotch disease (Pyrenophora teres), leaf blotch disease (Rhynchosporium secalis), loose smut disease (Ustilago tritici, U.nuda), and the like.


Rice: blast disease (Pyricularia oryzae), sheath blight disease (Rhizoctonia solani), bakanae disease (Gibberella fujikuroi), brown spot disease (Cochliobolus miyabeanus), damping-off disease (Pythium graminicolum), bacterial leaf blight (Xanthomonas oryzae), bacterial seedling blight disease (Burkholderia plantarii), brown stripe disease (Acidovorax avenae), bacterial grain rot disease (Burkholderia glumae), Cercospora leaf spot disease (Cercospora oryzae), false smut disease (Ustilaginoidea virens), rice brown spot disease (Alternaria alternata, Curvularia intermedia), kernel discoloration of rice (Alternaria padwickii), pink coloring of rice grains (Epicoccam purpurascenns), and the like.


Tobacco: sclerotinia rot disease (Sclerotinia sclerotiorum), powdery mildew disease (Erysiphe cichoracearum), phytophthora rot disease (Phytophthora nicotianae), and the like.


Tulip: gray mold disease (Botrytis cinerea), and the like.


Sunflower: downy mildew disease (Plasmopara halstedii), sclerotinia rot disease (Sclerotinia sclerotiorum), and the like.


Bent grass: Sclerotinia snow blight (Sclerotinia borealis), Large patch (Rhizoctonia solani), Dollar spot (Sclerotinia homoeocarpa), blast disease (Pyricularia sp.), Pythium red blight disease (Pythium aphanidermatum), anthracnose disease (Colletotrichum graminicola), and the like.


Orchard grass: powdery mildew disease (Erysiphe graminis), and the like.


Soybean: purple stain disease (Cercospora kikuchii), downy mildew disease (Peronospora manshurica), phytophthora rot disease (Phytophthora sojae), rust disease (Phakopsora pachyrhizi), sclerotinia rot disease (Sclerotinia sclerotiorum), anthracnose disease (Colletotrichum truncatum), gray mold disease (Botrytis cinerea), and the like.


Potato: hytophthora rot disease (Phytophthora infestans), early blight disease (Aleternaria solani), scurf disease (Thanatephorus cucumeris), and the like.


Banana: Panama disease (Fusarium oxysporum), Sigatoka disease (Mycosphaerella fijiensis, Mycosphaerella musicola), and the like.


Rape seed: sclerotinia rot disease (Sclerotinia sclerotiorum), root rot disease (Phoma lingam), black leaf spot disease (Alternaria brassicae), and the like.


Coffee: rust disease (Hemileia vastatrix), anthracnose (Colletotrichum coffeanum), leaf spot disease (Cercospora coffeicola), and the like.


Sugarcane: brown rust disease (Puccinia melanocephala), and the like.


Corn: zonate spot disease (Gloecercospora sorghi), rust disease (Puccinia sorghi), southern rust disease (Puccinia polysora), smut disease (Ustilago maydis), brown spot disease (Cochliobolus heterostrophus), northern leaf blight (Setophaeria turcica), and the like.


Cotton: seedling blight disease (Pythium sp), rust disease (Phakopsora gossypii), sour rot disease (Mycosphaerella areola), anthracnose (Glomerella gossypii), and the like.


The fungicide or plant disease-controlling agent according to the present invention is an agent with low phytotoxicity, low toxicity to fish or warm-blooded animals, and is safe to use.


The fungicide or plant disease-controlling agent according to the present invention may be mixed or used with other fungicides, insecticides, acaricides, nematocides, soil pesticides, anthelmintics, plant growth regulators, synergists, or the like.


Examples thereof are shown below.


Fungicide:

  • (1) Nucleic acid biosynthesis inhibitors:
  • (a) RNA polymerase I inhibitors: benalaxyl, benalaxyl-M, furalaxyl, metalaxyl, metalaxyl-M; oxadixyl; clozylacon, ofurace;
  • (b) Adenosine deaminase inhibitors: bupirimate, dimethirimol, ethirimol;
  • (c) DNA/RNA synthesis inhibitors: hymexazol, octhilinone;
  • (d) DNA topoisomerase II inhibitors: oxolinic acid;
  • (2) Mitotic inhibitors and cell division inhibitors:
  • (a) β-tubulin polymerization inhibitors: benomyl, carbendazim, chlorfenazole, fuberidazole, thiabendazole; thiophanate, thiophanate-methyl; diethofencarb; zoxamide; ethaboxam;
  • (b) Cell division inhibitors: pencycuron;
  • (c) Spectrin-like protein delocalization inhibitors: fluopicolide;
  • (3) Respiration inhibitors:
  • (a) Complex I NADH oxidation-reduction enzyme inhibitors: diflumetorimu; tolfenpyrad;
  • (b) Complex II succinate dehydrogenase inhibitors: benodanil, flutolanil, mepronil; isofetamide; fluopyram; fenfuram, furmecyclox; carboxin, oxycarboxin; thifluzamide; benzovindiflupyr, bixafen, fluxapyroxad, furametpyr, isopyrazam, penflufen, penthiopyrad, sedaxane; boscalid;
  • (c) Complex III ubiquinol oxidase Qo inhibitors: azoxystrobin, coumoxystrobin, coumethoxystrobin, enoxastrobin, flufenoxystrobin, picoxystrobin, pyraoxystrobin; pyraclostrobin, pyrametostrobin, triclopyricarb; kresoxim-methyl, trifloxystrobin; dimoxystrobin, fenaminstrobin, metominostrobin, orysastrobin; famoxadone; fluoxastrobin; fenamidone; pyribencarb;
  • (d) Complex III ubiquinol reductase Qi inhibitors: cyazofamid; amisulbrom;
  • (e) Oxidative phosphorylation uncoupling agenst: binapacryl, meptyldinocap, dinocap; fluazinam; ferimzone;
  • (f) Oxidative phosphorylation inhibitors (ATP synthase inhibitors): fentin acetate, fentin chloride, fentin hydroxide
  • (g) ATP production inhibitors: silthiofam:
  • (h) Complex III: Qx (unknown) inhibitor of cytochrome bc1 (ubiquinone reductase): ametoctradin;
  • (4) Amino acid and protein synthesis inhibitors
  • (a) Methionine biosynthesis inhibitors: andoprim, cyprodinil, mepanipyrim, pyrimethanil;
  • (b) Protein synthesis inhibitors: blasticidin-S; kasugamycin, kasugamycin hydrochloride; streptomycin; oxytetracycline;
  • (5) Signal transduction inhibitors:
  • (a) Signal transduction inhibitors: quinoxyfen, proquinazid;
  • (b) Inhibitors of MAP/histidine kinase in osmotic signal transduction: fenpiclonil, fludioxonil; chlozolinate, iprodione, procymidone, vinclozolin;
  • (6) Lipids and cell membrane synthesis inhibitors:
  • (a) Inhibitors of phospholipid biosynthesis or methyltransferase: edifenphos, iprobenfos, pyrazophos; isoprothiolane;
  • (b) Lipid peroxidation agent: biphenyl, chloroneb, dicloran, quintozene, tecnazene, tolclofos-methyl; etridiazole;
  • (c) Agents that act on cell membrane: iodocarb, propamocarb, propamocarb hydrochloride, propamocarb fosetylate, prothiocarb;
  • (d) Microorganisms that disrupt cell membrane of pathogens: Bacillus subtilis bacteria, Bacillus subtilis QST713 strain, Bacillus subtilis FZB24 strain, Bacillus subtilis MBI600 strain, Bacillus subtilis strain D747 strain;
  • (e) Agents that disrupt cell membrane: extract of Melaleuca alternifolia (tea tree).
  • (7) Inhibitors of sterol biosynthesis in cell membrane:
  • (a) Inhibitors of demethylation at the C14 position in sterol biosynthesis: triforine; pyrifenox, pyrisoxazole; fenarimol, flurprimidol, nuarimol; imazalil, imazalil sulfate, oxpoconazole, pefurazoate, procloraz, triflumizole, viniconazole;


azaconazole, bitertanol, bromuconazole, cyproconazole, diclobutrazol, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, fluconazole, fluconazole-cis, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, fluquinconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole; prothioconazole, voriconazole;

  • (b) Inhibitors of Δ14 reductase and Δ8→Δ7-isomerase in sterol biosynthesis: aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph; fenpropidin, piperalin; spiroxamine;
  • (c) Inhibitors of 3-keto reductase in C4 demethylation in sterol biosynthesis: fenhexamid; fenpyrazamine;
  • (d) Inhibitors of squalene epoxidase in sterol biosynthesis: pyributicarb; naftifin, terbinafine;
  • (8) Cell wall synthesis inhibitors
  • (a) Trehalase inhibitor: validamycin;
  • (b) Chitin synthesis inhibitors: polyoxin, polyoxorim;
  • (c) Cellulose synthase inhibitors: dimethomorph, flumorph, pyrimorph; benthiavalicarb, iprovalicarb, tolprocarb, valifenalate; mandipropamid;
  • (9) Melanin biosynthesis inhibitors
  • (a) Melanin biosynthesis reductase inhibitors: fthalide; pyroquilon, tricyclazole;
  • (b) Melanin biosynthesis anhydrase inhibitors: carpropamid; diclocymet; fenoxanil;
  • (10) Host plant resistance inducer:
  • (a) Agents that act on salicylic acid synthesis pathway: acibenzolar-S-methyl;
  • (b) Others: probenazole; tiadinil; isotianil; laminarin; Giant Knotweed Extract;
  • (11) Agents, action of which is unclear: cymoxanil, fosetyl aluminum, phosphoric acid (phosphate), tecloftalam, triazoxide, flusulfamide, diclomezine, methasulfocarb, cyflufenamid, metrafenone, piriofenon, dodine, dodine free base, flutianil;
  • (12) Agents having multi-functional points: copper (copper salt), Bordeaux mixture, copper hydroxide, copper naphthalate, copper oxide, copper oxychloride, copper sulfate, sulfur, sulfur products, calcium polysulfide; ferbam, mancozeb, maneb, mancopper, metiram, polycarbamate, propineb, thiram, zineb, ziram; captan, captafol, folpet; chlorothalonil; dichlofluanid, tolylfluanid; guazatine, iminoctadine triacetate, iminoctadine trialbesilate; anilazine; dithianon; chinomethionate; fluoroimide;
  • (13) Other agents: DBEDC, fluoro folpet, guazatine acetate, bis (8-quinolinolato) copper (II), propamidine, chloropicrin, cyprofuram, agrobacterium, bethoxazin, diphenylamine, methyl isothiocyanate (MITC), mildiomycin, capsaicin, cufraneb, cyprosulfamide, dazomet, debacarb, dichlorophene, difenzoquat, difenzoquat methyl sulfonate, flumetover, fosetyl calcium, fosetyl sodium, irumamycin, natamycin, nitrothal-isopropyl, oxamocarb, sodium propanosine, pyrrolnitrin, tebufloquin, tolnifanide, zarilamid, algophase, amicarthiazol, oxathiapiprolin, metiram zinc, benthiazole, trichlamide, uniconazole, mildiomycin, oxyfenthiin, picarbutrazox;


    Insecticides, Acaricides, Nematocides, Soil Pesticides:
  • (1) Acetylcholinesterase inhibitors:
  • (a) Carbamates: alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC, xylylcarb, fenothiocarb, MIPC, MPMC, MTMC, aldoxycarb, allyxycarb, aminocarb, bufencarb, chloethocarb, metam sodium, promecarb;
  • (b) Organophosphate-based: acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chloroethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isocarbophos, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimphos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, vamidothion; bromophos-ethyl, BRP, carbophenothion, cyanofenphos, CYAP, demeton-S-methylsulfone, dialifos, dichlofenthion, dioxabenzofos, etrimfos, fensulfothion, flupyrazofos, fonofos, formothion, phosmethylan, isazophos, iodofenphos, methacrifos, pirimiphos-ethyl, phosphocarb, propaphos, prothoate, sulprophos;
  • (2) GABAergic chloride ion channel antagonists: chlordene, endosulfan, ethiprole, fipronil, pyrafluoprole, pyriprole; camphlechlor, heptachlor, dienochlor;
  • (3) Sodium channel modulators: acrinathrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cyclopentyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin [(1R)-trans isomers], deltamethrin, empenthrin [(EZ)-(1R)-isomer], esfenvalerate, ethofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadethrin, permethrin, phenothrin [(1R)-trans isomer], prallethrin, pyrethrum, resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R)-isomer], tralomethrin, transfluthrin; allethrin, pyrethrin, pyrethrin I, pyrethrin II, profluthrin, dimefluthrin, bioethanomethrin, biopermethrin, transpermethrin, fenfluthrin, fenpirithrin, flubrocythrinate, flufenprox, metofluthrin, protrifenbute, pyresmethrin, terallethrin;
  • (4) Nicotinic acetylcholine receptor agonist: acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine, thiacloprid, thiamethoxam, sulfoxaflor, nicotine, flupyradifurone;
  • (5) Nicotinic acetylcholine receptor allosteric modulators: spinetoram, spinosad;
  • (6) Chloride channel activators: abamectin, emamectin benzoate, lepimectin, milbemectin; ivermectin, selamectin, doramectin, eprinomectin, moxidectin, milbemycin, milbemycin oxime;
  • (7) Juvenile hormone-like substances: hydroprene, kinoprene, methoprene, fenoxycarb, pyriproxyfen; diofenolan, epofenonane, triprene;
  • (8) Other non-specific inhibitors: methyl bromide, chloropicrin, sulfuryl fluoride, borax, tartar emetic;
  • (9) Homoptera selective feeding inhibitors: flonicamid, pymetrozine, pyrifluquinazon;
  • (10) Mite growth inhibitors: clofentezine, diflovidazin, hexythiazox, etoxazole;
  • (11) Insect's midgut inner membrane disrupting agent derived from microorganisms: Bacillus thuringiensis subspecies Isuraerenshi, Bacillus sphaericus, Bacillus thuringiensis subsp. Aizawai, Bacillus thuringiensis subspecies Kurstaki, Bacillus thuringiensis subspecies Tenebrionis, Bt crop protein: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1/Cry35Ab1;
  • (12) Mitochondrial ATP biosynthetic enzyme inhibitors: diafenthiuron, azocyclotin, cyhexatin, fenbutatin oxide, propargite, tetradifon;
  • (13) Oxidative phosphorylation uncouplers: chlorfenapyr, sulfluramid, DNOC; binapacryl, dinobuton, dinocap;
  • (14) Nicotinic acetylcholine receptor channel blockers: bensultap, cartap hydrochloride; nereistoxin; thiosultap sodium, thiocyclam;
  • (15) Chitin synthesis inhibitors: bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron, buprofezin, fluazuron;
  • (16) Diptera molting disrupting agents: cyromazine;
  • (17) Molting hormone receptor agonists: chromafenozide, halofenozide, methoxyfenozide, tebufenozide;
  • (18) Octopamine receptor agonists: amitraz, demiditraz, chlordimeform;
  • (19) Mitochondrial electron transport system complex III inhibitors: acequinocyl, fluacrypyrim, hydramethylnon;
  • (20) Mitochondrial electron transport system complex I inhibitors: fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad, rotenone;
  • (21) Voltage-dependent sodium channel blockers: indoxacarb, metaflumizone;
  • (22) Acetyl CoA carboxylase inhibitors: spirodiclofen, spiromesifen, spirotetramat;
  • (23) Mitochondrial electron transport system complex IV inhibitors: aluminum phosphide, calcium phosphide, phosphine, zinc phosphide, cyanide;
  • (24) Mitochondrial electron transport system complex II inhibitors: cyenopyrafen, cyflumetofen, pyflubumide;
  • (25) Ryanodine receptor modulators: chlorantraniliprole, cyantraniliprole, flubendiamide, cyclaniliprole, tetraniliprole;
  • (26) Mixed function oxidase inhibitor compounds: piperonyl butoxide;
  • (27) Latrophilin receptor agonists: depsipeptide, cyclic depsipeptide, 24-membered cyclic depsipeptide, emodepside;
  • (28) Other agents (mechanism of which has not been known): azadirachtin, benzoximate, bifenazate, bromopropylate, chinomethionate, cryolite, dicofol, pyridalyl; benclothiaz, sulfur, amidoflumet, 1,3-dichloropropene, DCIP, phenisobromolate, benzomate, metaldehyde, chlorobenzilate, clothiazoben, dicyclanil, fenoxacrim, fentrifanil, flubenzimin, fluphenazine, gossyplure, japonilure, metoxadiazone, oil, potassium oleate, tetrasul, triarathene; afidopyropen, flometoquin, flufiprole, fluensulfone, meperfluthrin, tetramethylfluthrin, tralopyril, dimefluthrin, methylneodecanamide; fluralaner, afoxolaner, fluxametamide, 5-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-(1H-1,2,4-triazol-1-yl) benzonitrile (CAS: 943137-49-3), broflanilide, other meta-diamides.


The following examples illustrate the present invention more specifically. The present invention is not intended to be limited to the following examples, may be practiced with appropriate modifications within the scope adaptable to the gist of the present invention, and all of which are encompassed in the technical scope of the present application.


EXAMPLE 1
Synthesis of tert-butyl N-[4-[3-[3-[3-[4-(N-tert-butoxycarbonylcarbamimidoyl)phenoxy]propyl]-2-imino-imidazolidin-1-yl]propoxy]benzenecarboximidoyl]carbamate



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Tert-butyl((4-(3-bromopropoxy)phenyl)(imino)methyl)carbamate (697 mg) was dissolved in N, N-dimethylformamide (7 mL). Potassium carbonate (1.15 g) and 2-amino-imidazoline hydrobromide (500 mg) were added to the resultant at room temperature. The resultant mixture was stirred at 40° C. for 6 hours. The resultant mixture was cooled to room temperature, and then water was added thereto to conduct extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound (compound No. 1: 99.4 mg, in a yield of 3.7%).



1HNMR (CDCl3): 1.55 (s, 18H), 2.00-2.11 (m, 4H), 3.27 (s, 4H), 3.36 (t, 4H), 4.06 (t, 4H), 6.88 (d, 4H), 7.81 (d, 4H).


EXAMPLE 2
Synthesis of hydrochloride salt of 4-[3-[3-[3-(4-carbamimidoylphenoxy)propyl]-2-imino-imidazolidin-1-yl]propoxy]benzamidine



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The tert-butyl N-[4-[3-[3-[3-[4-(N-tert-butoxycarbonylcarbamimidoyl)phenoxy]propyl]-2-imino-imidazolidin-1-yl]propoxy]benzenecarboximidoyl]carbamate (99 mg) obtained in Example 1 was dissolved in dichloromethane (1 mL). Trifluoroacetic acid (1 mL) was added to the resultant at room temperature and the mixture was stirred at the same temperature overnight. The resultant mixture was concentrated under reduced pressure, and the residue was dissolved in methanol (1 mL). Hydrogen chloride (4M in dioxane solution, 1 mL) was added to the resultant at room temperature. The resultant mixture was stirred at room temperature for 1 hour. Then, the resultant was concentrated under reduced pressure to obtain the title compound (compound No. 2: 77 mg).



1HNMR (CD3OD): 1.29-1.41 (m, 4H), 2.08-2.18 (m, 4H), 3.55 (t, 4H), 4.18 (t, 4H), 7.16 (d, 4H), 7.80 (d, 4H).


EXAMPLE 3
Synthesis of tert-butyl-N-[[6-[3-[6-[[N,N′-bis(tert-butoxycarbonyl)carbamimidoyl]amino]hexyl]-2-imino-imidazolidin-1-yl]hexylamino]-(tert-butoxycarbonylamino)methylene]carbamate



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The title compound (compound No. 3) was obtained in the same manner as in Example 1.



1HNMR (CDCl3): 1.32-1.41 (m, 10H), 1.48-1.52 (m, 36H), 1.52-1.64 (m, 10H), 3.21 (s, 4H), 3.87-3.96 (m, 4H).


EXAMPLE 4
Synthesis of hydrochloride salt of 1-[6-[3-(6-guanidinohexyl)-2-imino-imidazolidin-1-yl]hexyl]guanidine



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The title compound (compound No. 4) was obtained in the same manner as in Example 2.



1HNMR (CD3OD): 1.34-1.52 (m, 10H), 1.54-1.71 (m, 10H), 3.14-3.23 (m, 4H), 3.66-3.69 (m, 4H).


EXAMPLE 5
Synthesis of tert-butyl N-[4-[4-[3-[4-[4-(N-tert-butoxycarbonylcarbamimidoyl)phenoxy]butyl]-2-imino-imidazolidin-1-yl]butoxy]benzenecarboximidoyl]carbamate



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The title compound (compound No. 5) was obtained in the same manner as in Example 1.



1HNMR (CDCl3): 1.55 (s, 18H), 1.57-1.78 (m, 12H), 1.79-1.91 (m, 4H), 4.02 (t, 4H), 6.89 (d, 4H), 7.82 (d, 4H).


EXAMPLE 6
Synthesis of hydrochloride salt of 4-[4-[3-[4-(4-carbamimidoylphenoxy)butyl]-2-imino-imidazolidin-1-yl]butoxy]benzamidine



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The title compound (compound No. 6) was obtained in the same manner as in Example 2.



1HNMR (CD3OD): 1.75-1.96 (m, 8H), 3.37-3.46 (m, 4H), 3.67-3.70 (m, 4H), 4.10-4.18 (m, 4H), 7.13 (d, 4H), 7.79 (d, 4H).


EXAMPLE 7
Synthesis of tert-butyl N-[[7-[3-[7-[[N,N′-bis(tert-butoxycarbonyl)carbamimidoyl]amino]heptyl]-2-imino-imidazolidin-1-yl]heptylamino]-(tert-butoxycarbonylamino)methylene]carbamate



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The title compound (compound No. 7) was obtained in the same manner as in Example 1.



1HNMR (CDCl3): 1.27-1.38 (m, 14H), 1.47-1.59 (m, 42H), 3.16-3.00 (m, 4H), 3.20 (s, 4H), 3.88 (dd, 4H).


EXAMPLE 8
Synthesis of hydrochloride salt of 1-[7-[3-(7-guanidinoheptyl)-2-imino-imidazolidin-1-yl]heptyl]guanidine



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The title compound (compound No. 8) was obtained in the same manner as in Example 2.



1HNMR (CD3OD): 1.36-1.47 (m, 12H), 1.54-1.69 (m, 8H), 3.10-3.22 (m, 4H), 3.30-3.44 (m, 4H), 3.58-3.72 (m, 4H).


EXAMPLE 9
(Step 1) Synthesis of tert-butyl N-(4-bromobutyl)-N-[N-(4-bromobutyl)-N,N′-bis (tert-butoxycarbonyl)carbamimidoyl]carbamate



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Tert-butyl N-[bis(tert-butoxycarbonylamino)methylene]carbamate (1 g) was dissolved in tetrahydrofuran (7 mL). Triphenylphosphine (1.83 g), 4-bromobutane-1-ol (1.07 g), and diethyl azodicarboxylate (2.2M in toluene solution, 3.2 mL) were added to the resultant under ice-cooling. The mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was subj ected to extraction with ethyl acetate. The resultant organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain the title compound (935 mg, in a yield of 53.4%).



1HNMR (CDCl3): 1.48 (s, 27H), 1.74-1.95 (m, 8H), 3.42 (t, 4H), 3.56 (dd, 4H).


(Step 2) Synthesis of tert-butyl N-[N,N′-bis(tert-butoxycarbonyl)-N-[4-[4-(N-tert-butoxycarbonylcarbamimidoyl)phenoxy]butyl]carbamimidoyl]-N-[4-[4-(N-tert-butoxy carbonylcarbamimidoyl)phenoxy]butyl]carbamate



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The tert-butyl N-(4-bromobutyl)-N-[N-(4-bromobutyl)-N,N′-bis(tert-butoxy carbonyl)carbamimidoyl]carbamate (400 mg) obtained in the step 1 was dissolved in acetonitrile (5 mL). Potassium carbonate (263 mg) and tert-butyl N-(4-hydroxybenzene carboximidoyl)carbamate (330 mg) were added to the resultant. The reaction mixture was stirred overnight while heating the reaction mixture under reflux. The reaction mixture was cooled to room temperature, water was added to the reaction mixture, and the resultant was subjected to extraction with ethyl acetate. The resultant organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain the title compound (compound No. 9: 292 mg, in a yield of 48.8%).



1HNMR (CDCl3): 1.45-1.60 (m, 45H), 1.74-1.92 (m, 8H), 3.61 (dd, 4H), 3.94 (t, 4H), 6.78 (d, 4H), 7.75 (d, 4H).


EXAMPLE 10
Synthesis of hydrochloride salt of 4-[4-[[N-[4-(4-carbamimidoylphenoxy)butyl]carbamimidoyl]amino]butoxy]benzamidine



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The title compound (compound No. 10) was obtained in the same manner as in Example 2.



1HNMR (CD3OD): 1.75-1.95 (m, 8H), 3.34-3.45 (m, 4H), 4.14 (t, 4H), 7.14 (d, 4H), 7.78 (d, 4H).


EXAMPLE 11
(Step 1) Synthesis of tert-butyl N-(7-bromoheptyl)-N-[N-(7-bromoheptyl)-N,N′-bis (tert-butoxycarbonyl)carbamimidoyl]carbamate



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The title compound was obtained in the same manner as in Step 1 of Example 9.



1HNMR (CDCl3): 1.25-1.40 (m, 8H), 1.44-1.56 (m, 31H), 1.60-1.71 (m, 4H), 1.85 (tt, 4H), 3.39 (t, 4H), 3.52 (dd, 4H).


(Step 2) Synthesis of tert-butyl N-[7-[[N,N′-bis(tert-butoxycarbonyl)carbamimidoyl]amino]heptyl]-N-[N-[7-[[N,N′-bis(tert-butoxycarbonyl)carbamimidoyl]amino]heptyl]-N, N′-bis(tert-butoxycarbonyl)carbamimidoyl]carbamate



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The tert-butyl N-(7-bromoheptyl)-N-[N-(7-bromoheptyl)-N,N′-bis(tert-butoxy carbonyl)carbamimidoyl]carbamate (400 mg) obtained in the step 1 was dissolved in N, N-dimethylformamide (5 mL). Potassium carbonate (232 mg) and tert-butyl N-[amino(tert-butoxycarbonylamino)methylene]carbamate (363 mg) were added to the resultant at room temperature. The resultant was stirred at 50° C. overnight, and then the reaction mixture was cooled to room temperature. Water was added to the reaction mixture, and the mixture was subjected to extraction with ethyl acetate. The resultant organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain the title compound (compound No. 11: 404 mg, in a yield of 67.3%).



1HNMR (CDCl3): 1.24-1.40 (m, 12H), 1.47-1.60 (m, 63H), 1.54-1.76 (m, 8H), 3.47 (dd, 4H), 3.87 (t, 4H).


EXAMPLE 12
Synthesis of hydrochloride salt of 1,3-bis(7-guanidinoheptyl)guanidine



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The title compound (compound No. 12) was obtained in the same manner as in Example 2.



1HNMR (CD3OD): 1.37-1.45 (m, 12H), 1.55-1.66 (m, 8H), 3.14-3.24 (m, 8H).


EXAMPLE 13
Synthesis of tert-butyl N-[N,N′-bis(tert-butoxycarbonyl)-N-[7-[4-(N-tert-butoxycarbonyl carbamimidoyl)phenoxy]heptyl]carbamimidoyl]-N-[7-[4-(N-tert-butoxycarbonylcarbamimidoyl)phenoxy]heptyl]carbamate



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The title compound (compound No. 13) was obtained in the same manner as in Example 9.



1HNMR (CDCl3): 1.20-1.42 (m, 8H), 1.42-1.55 (m, 49H), 1.57-1.65 (m, 4H), 1.77 (tt, 4H), 3.49 (dd, 4H), 3.95 (t, 4H), 6.85 (d, 4H), 7.78 (d, 4H).


EXAMPLE 14
Synthesis of hydrochloride salt of 4-[7-[[N-[7-(4-carbamimidoylphenoxy)heptyl]carbamimidoyl]amino]heptoxy]benzamidine



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The title compound (compound No. 14) was obtained in the same manner as in Example 2.



1HNMR (CD3OD): 1.39-1.50 (m, 8H), 1.52-1.63 (m, 4H), 1.59-1.64 (m, 4H), 1.83 (tt, 4H), 3.19 (t, 4H), 4.09 (t, 4H), 7.11 (d, 4H), 7.78 (d, 4H).


EXAMPLE 15
(Step 1) Synthesis of tert-butyl N-[N,N′-bis(tert-butoxycarbonyl)carbamimidoyl]-N-[4-[4-(N-tert-butoxycarbonylcarbamimidoyl)phenoxy]butyl]carbamate



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The title compound was obtained in the same manner as in the step 2 of Example 11 using tert-butyl ((4-(4-bromobutoxy)phenyl)(imino)methyl)carbamate and tert-butyl N-[bis(tert-butoxycarbonylamino)methylene]carbamate.



1HNMR (CDCl3): 1.42-1.56 (m, 36H), 1.80-1.86 (m, 4H), 3.87 (dd, 2H), 4.01 (dd, 2H), 6.91 (d, 2H), 7.82 (d, 2H).


(Step 2) Synthesis of tert-butyl N-[N,N′-bis(tert-butoxycarbonyl)-N-[4-[4-(N-tert-butoxy carbonylcarbamimidoyl)phenoxy]butyl]carbamimidoyl]-N-(7-bromoheptyl)carbamate



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The title compound was obtained in the same manner as in the step 1 of Example 9 using the tert-butyl N-[N,N′-bis(tert-butoxycarbonyl)carbamimidoyl]-N-[4-[4-(N-tert-butoxycarbonylcarbamimidoyl)phenoxy]butyl]carbamate obtained in the step 1.



1HNMR (CDCl3): 1.21-1.34 (m, 4H), 1.42-1.49 (m, 38H), 1.61-1.70 (m, 2H), 1.78-1.89 (m, 6H), 3.38 (t, 2H), 3.51 (dd, 2H), 3.58 (dd, 2H), 4.00 (t, 2H), 6.89 (d, 2H), 7.82 (d, 2H).


(Step 3) Synthesis of tert-butyl N-[N,N′-bis(tert-butoxycarbonyl)-N-[4-[4-(N-tert-butoxy carbonylcarbamimidoyl)phenoxy]butyl]carbamimidoyl]-N-[7-[[N,N′-bis(tert-butoxy carbonyl)carbamimidoyl]amino]heptyl]carbamate



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The title compound (compound No. 15) was obtained in the same manner as in the step 2 of Example 11 using the tert-butyl N-[N,N′-bis(tert-butoxycarbonyl)-N-[4-[4-(N-tert-butoxycarbonylcarbamimidoyl)phenoxy]butyl]carbamimidoyl]-N-(7-bromoheptyl)carbamate obtained in the step 2.



1HNMR (CDCl3): 1.12-1.36 (m, 8H), 1.42-1.52 (m, 54H), 1.76-1.90 (m, 6H), 3.43-3.50 (m, 2H), 3.56-3.63 (m, 2H), 3.82 (dd, 2H), 4.00 (t, 2H), 6.88 (d, 2H), 7.88 (d, 2H).


EXAMPLE 16
Synthesis of hydrochloride salt of 4-[4-[[N-(7-guanidinoheptyl)carbamimidoyl]amino]butoxy]benzamidine



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The title compound (compound No. 16) was obtained in the same manner as in Example 2.



1HNMR (CD3OD): 1.36-1.44 (m, 8H), 1.54-1.67 (m, 4H), 1.76-1.93 (m, 4H), 3.10-3.24 (m, 4H), 4.14 (t, 2H), 7.14 (d, 2H), 7.79 (d, 2H).


EXAMPLE 17
Synthesis of hydrochloride salt of 6,6′-((((iminomethylene)bis(azanediyl))bis (propane-3,1-diyl))bis(oxy))dinicotinimidamide



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Ttert-butyl ((6-(3-hydroxypropoxy)pyridin-3-yl)(imino)methyl)carbamate (0.53 g) was dissolved in tetrahydrofuran (8 mL). Tert-butyl N-[bis(tert-butoxycarbonylamino) methylene]carbamate (0.36 g) was added to the resultant at room temperature. Triphenylphosphine (0.66 g) and diethyl azodicarboxylate (1.2 mL, 2.2 M in toluene solution) were added to the resultant at room temperature. The mixture was stirred for 24 hours, and then the solvent was distilled off from the reaction mixture. The residue was purified by silica gel column chromatograph. The obtained crude product was dissolved in dichloromethane (3 mL), and then trifluoroacetic acid (1.5 mL) was added to the solution. After the mixture was stirred at room temperature for 72 hours, the solvent was distilled off from the reaction mixture. The crude product was dissolved in methanol (3 mL), and then hydrogen chloride (3 mL, 4M in 1,4-dioxane solution) was added to the solution. The mixture was stirred at room temperature for 18 hours, and then the solvent was distilled off from the reaction mixture to obtain the title compound (compound No. 17: 0.23 g).



1HNMR (CDCl3): 2.16 (m, 4H), 3.48 (m, 4H), 4.58 (m, 4H), 7.32 (d, 2H), 8.37 (d, 2H), 8.79 (s, 2H).


EXAMPLE 18
Synthesis of tert-butyl N-[4-[3-[3-[3-[4-(N-tert-butoxycarbonylcarbamimidoyl)phenoxy]propyl]-2-(2,2,2-trifluoroacetyl)imino-imidazol-1-yl]propoxy]benzenecarboximidoyl]carbamate



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N-(1,3-dihydroimidazole-2-ylidene)-2,2,2-trifluoroacetamide (250 mg) was dissolved in acetonitrile (5 mL) and benzene (2 mL). Potassium carbonate (580 mg) and tert-butyl N-[4-(3-bromopropoxy)benzenecarboximidoyl]carbamate (1.09 g) were added to the solution at room temperature. The reaction mixture was heated to 50° C., and then stirred at the same temperature overnight. The reaction mixture was cooled to room temperature, water was added thereto, and then the mixture was subjected to extraction with ethyl acetate. The resultant organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain the title compound (compound No. 18: 465 mg, in a yield of 45.6%) and a compound A (183 mg, in a yield of 28.8%).

  • Compound No. 18:



1HNMR (CDCl3): 1.55 (s, 18H), 2.25 (tt, 4H), 3.95 (t, 4H), 4.11 (t, 4H), 6.67 (d, 2H), 6.84 (d, 4H), 7.81 (d, 4H).

  • Compound A:


Tert-butyl N-[4-[3-[2-(2,2,2-trifluoroacetyl)imino-1H-imidazol-3-yl]propoxy]benzene carboximidoyl]carbamate



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1HNMR (CDCl3): 1.55 (s, 9H), 2.30 (tt, 2H), 4.02 (t, 2H), 4.23 (t, 2H), 6.64 (d, 1H), 6.77 (d, 1H), 6.89 (d, 2H), 7.83 (d, 2H).


EXAMPLE 19
Synthesis of tert-butyl N-[4-[3-[3-[3-[4-(N-tert-butoxycarbonylcarbamimidoyl)phenoxy]propyl]-2-imino-imidazol-1-yl]propoxy]benzenecarboximidoyl]carbamate



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The tert-butyl N-[4-[3-[3-[3-[4-(N-tert-butoxycarbonylcarbamimidoyl)phenoxy]propyl]-2-(2,2,2-trifluoroacetyl)imino-imidazol-1-yl]propoxy]benzenecarboximidoyl]carbamate (465 mg) obtained in Example 18 was dissolved in methanol (5 mL). Potassium carbonate (97 mg) was added to the solution at room temperature. Then, the mixture was stirred at 60° C. overnight. The reaction mixture was cooled to room temperature, and then the resultant was concentrated under reduced pressure. Water was added to the resulting residue, and the mixture was subjected to extraction with ethyl acetate. The resultant organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain the title compound (compound No. 19: 139 mg, in a yield of 34.3%).



1H NMR (CDCl3): 1.55 (s, 18H), 2.16 (tt, 4H), 3.77 (t, 4H), 3.99 (t, 4H), 6.01 (s, 2H), 6.88 (d, 4H), 7.81 (d, 4H).


EXAMPLE 20
Synthesis of hydrochloride salt of 4-[3-[3-[3-(4-carbamimidoylphenoxy)propyl]-2-imino-imidazol-1-yl]propoxy]benzamidine



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The title compound (compound No. 20) was obtained in the same manner as in Example 2.

  • Melting point (mp): 284-286° C.


EXAMPLE 21
Synthesis of tert-butyl N-[N,N′-bis(tert-butoxycarbonyl)-N-[5-[4-(N-tert-butoxycarbonyl carbamimidoyl)phenyl]pent-4-ynyl]carbamimidoyl]-N-[5-[4-(N-tert-butoxycarbonyl carbamimidoyl)phenyl]pent-4-ynyl]carbamate



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Tert-butyl N-[bis(tert-butoxycarbonylamino)methylene]carbamate (360 mg) was dissolved in tetrahydrofuran (4 mL). Tert-butyl N-[4-(5-bromopent-1-ynyl) benzenecarboximidoyl]carbamate (194 mg), triphenylphosphine (312 mg), and diisopropyl azodicarboxylate (2.2M in toluene solution) (541 μL) were added to the solution under ice-cooling. The reaction mixture was warmed to room temperature and then stirred at the same temperature overnight. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain the title compound (compound No. 21: 268 mg, in a yield of 53.4%).



1HNMR (CDCl3): 1.47-1.59 (m, 45H), 1.98 (tt, 4H), 2.47 (t, 4H), 3.69 (dd, 4H), 7.38 (d, 4H), 7.71 (d, 4H).


EXAMPLE 22
Synthesis of hydrochloride salt of 4-[5-[[N-[5-(4-carbamimidoylphenyl)pent-4-ynyl]carbamimidoyl]amino]pent-1-ynyl]benzamidine



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The title compound (compound No. 22) was obtained in the same manner as in Example 2.



1HNMR (CD3OD): 1.91 (tt, 4H), 2.59 (t, 4H), 3.38 (t, 4H), 7.62 (d, 4H), 7.76 (d, 4H).


EXAMPLE 23
(Step 1) synthesis of tert-butyl N-[4-[3-[3-(7-bromoheptyl)-2-(2,2,2-trifluoroacetyl)imino-imidazol-1-yl]propoxy]benzenecarboximidoyl]carbamate



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The tert-butyl N-[4-[3-[2-(2,2,2-trifluoroacetyl)imino-1H-imidazol-3-yl]propoxy]benzenecarboximidoyl]carbamate (compound A: 297 mg) obtained in Example 18 was dissolved in acetonitrile (6 mL). Potassium carbonate (99 mg) and 1,7-dibromoheptane (709 mg) were added to the solution at room temperature. The mixture was stirred at 60° C. overnight, and the reaction mixture was cooled to room temperature. Then, the reaction mixture was concentrated under reduced pressure, water was added to the resulting residue, and then the mixture was subjected to extraction with ethyl acetate. The resultant organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain the title compound (172 mg, in a yield of 40.8%).



1HNMR (CDCl3): 1.28-1.36 (m, 6H), 1.55 (s, 9H), 1.64-1.79 (m, 2H), 1.80-1.90 (m, 2H), 2.25 (tt, 2H), 3.40 (t, 2H), 3.84 (dd, 2H), 3.98 (t, 2H), 4.12 (t, 2H), 6.70 (s, 2H), 6.89 (d, 2H), 7.82 (d, 2H).


(Step 2) Synthesis of tert-butyl N-[4-[3-[3-[7-[[N,N′-bis(tert-butoxycarbonyl) carbamimidoyl]amino]heptyl]-2-(2,2,2-trifluoroacetyl)imino-imidazol-1-yl]propoxy]benzenecarboximidoyl]carbamate



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The title compound (compound No. 23) was obtained in the same manner as in step 2 of Example 11.



1HNMR (CDCl3): 1.23-1.36 (m, 6H), 1.44-1.60 (m, 29H), 1.63-1.76 (m, 2H), 2.25 (tt, 2H), 3.82-3.92 (m, 4H), 3.98 (t, 2H), 4.12 (t, 2H), 6.70 (s, 2H), 6.89 (d, 2H), 7.85 (d, 2H).


EXAMPLE 24
Synthesis of tert-butyl N-[4-[3-[3-[7-[[N,N′-bis(tert-butoxycarbonyl)carbamimidoyl]amino]heptyl]-2-imino-imidazol-1-yl]propoxy]benzenecarboximidoyl]carbamate



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The title compound (compound No. 24) was obtained in the same manner as in Example 19.



1HNMR (CDCl3): 1.26-1.36 (m, 6H), 1.47-1.64 (m, 29H), 1.66-1.75 (m, 2H), 2.26 (tt, 2H), 3.11 (t, 2H), 3.85 (t, 2H), 3.98 (t, 2H), 4.11 (t, 2H), 6.71-6.74 (m, 2H), 6.89 (d, 2H), 7.83 (d, 2H).


EXAMPLE 25
Synthesis of hydrochloride salt of 4-[3-[3-(7-guanidinoheptyl)-2-imino-imidazol-1-yl]propoxy]benzamidine



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The title compound (compound No. 25) was obtained in the same manner as in Example 2



1HNMR (CD3OD): 1.33-1.42 (m, 6H), 1.52-1.64 (m, 2H), 1.72-1.79 (m, 2H), 2.25-2.33 (m, 2H), 3.16 (t, 2H), 3.86 (t, 2H), 4.12-4.22 (m, 4H), 6.97 (s, 2H), 7.14 (d, 2H), 7.81 (d, 2H).


EXAMPLE 26
Synthesis of tert-Butyl N-[4-[4-[3-[4-[4-(N-tert-butoxycarbonylcarbamimidoyl)phenoxy]butyl]-2-imino-benzimidazol-1-yl]butoxy]benzenecarboximidoyl]carbamate



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1,3-dihydro-benzimidazol-2-imine (200 mg) was dissolved in acetonitrile (15 mL). Potassium carbonate (414 mg), tetrabutylammonium bromide (73 mg) and tert-butyl N-[4-(4-bromobutoxy)benzenecarboximidoyl]carbamate (1.11 g) were added to the solution under ice-cooling. Then, the mixture was stirred at room temperature overnight. Then, the reaction mixture was heated to 60° C., and stirred at the same temperature for 5 hours. N, N-dimethylformamide (5 mL) was added to the reaction mixture, and then the mixture was heated to 80° C. and stirred at the same temperature overnight. The reaction mixture was cooled to room temperature and was concentrated under reduced pressure. Water was added to the resulting residue, and the mixture was subjected to extraction with ethyl acetate. The resultant organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain the title compound (compound No. 26: 121 mg, in a yield of 11.3%).



1HNMR (CDCl3): 1.55 (s, 18H), 1.82-2.00 (m, 8H), 3.84-3.94 (m, 4H), 4.02 (t, 4H), 6.83-6.85 (m, 6H), 6.99 (dd, 2H), 7.79 (d, 4H).


EXAMPLE 27
Synthesis of hydrochloride salt of 4-[4-[3-[4-(4-carbamimidoylphenoxy)butyl]-2-imino-benzimidazol-1-yl]butoxy]benzamidine



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The title compound (compound No. 27) was obtained in the same manner as in Example 2.



1HNMR (CD3OD): 1.87-2.12 (m, 8H), 4.16 (t, 4H), 4.30 (t, 4H), 7.11 (d, 4H), 7.40 (dd, 2H), 7.57 (dd, 2H), 7.77 (d, 4H).


EXAMPLE 28
(Step 1) Synthesis of tert-butyl N-[N,N′-bis(tert-butoxycarbonyl)-N-[3-[4-(N-tert-butoxycarbonylcarbamimidoyl)phenoxy]propyl]carbamimidoyl]-N-(7-bromoheptyl) carbamate



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Tert-butyl N-(7-bromoheptyl)-N-[N-tert-butoxycarbonyl-N′-isopropoxycarbonyl-carbamimidoyl]carbamate (480 mg) was dissolved in tetrahydrofuran (7 mL). Triphenylphosphine (304 mg), tert-butyl N-[4-(3-hydroxypropoxy)benzenecarboximidoyl]carbamate (342 mg), and diethyl azodicarboxylate (2.2 M in toluene solution) (527 μL) were added to the solution under ice-cooling. The mixture was stirred at room temperature overnight, and the reaction mixture was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound (365 mg, in a yield of 50.2%).



1HNMR (CDCl3): 1.24-1.36 (m, 4H), 1.46-1.55 (m, 38H), 1.59-1.68 (m, 2H), 1.83 (tt, 2H), 2.16 (tt, 2H), 3.38 (t, 2H), 3.49 (dd, 2H), 3.73 (dd, 2H), 4.07 (t, 2H), 6.90 (d, 2H), 7.82 (d, 2H).


(Step 2) Synthesis of tert-butyl N-[N,N′-bis(tert-butoxycarbonyl)-N-[3-[4-(N-tert-butoxy carbonylcarbamimidoyl)phenoxy]propyl]carbamimidoyl]-N-[7-[[N,N′-bis(tert-butoxy carbonyl)carbamimidoyl]amino]heptyl]carbamate



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The title compound (compound No. 28) was obtained in the same manner as in the step 2 of Example 11.



1HNMR (CDCl3): 1.10-1.22 (m, 6H), 1.47-1.62 (m, 58H), 2.10-2.22 (m, 2H), 3.63-3.53 (m, 2H), 3.74 (t, 2H), 3.81 (t, 2H), 4.07 (d, 2H), 6.90 (d, 2H), 7.93 (d, 2H).


EXAMPLE 29
Synthesis of hydrochloride salt of 4-[3-[[N-(7-guanidinoheptyl)carbamimidoyl]amino]propoxy]benzamidine



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The title compound (compound No. 29) was obtained in the same manner as in Example 2.



1HNMR (CD3OD): 1.35-1.46 (m, 6H), 1.54-1.66 (m, 4H), 2.08-2.15 (m, 2H), 3.16-3.24 (m, 4H), 3.41-3.46 (m, 2H), 4.19 (t, 2H), 7.16 (d, 2H), 7.80 (d, 2H).


EXAMPLE 30
Synthesis of acetic acid salt of 4-[4-[[N-(7-guanidinoheptyl)carbamimidoyl]amino]butoxy]benzamidine



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The hydrochloride salt of 4-[4-[[N-(7-guanidinoheptyl)carbamimidoyl]amino]butoxy]benzamidine (390 mg) obtained in Example 16 was dissolved in dichloromethane (2.5 mL) and methanol (1.5 mL). A 10% aqueous solution of sodium hydroxide (3 mL) was added to the solution at room temperature. The mixture was further stirred for 1 hour at room temperature. Water was added to the reaction mixture, and the mixture was subjected to extraction with a mixture solvent composed of dichloromethane and methanol (2:1). The resultant organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was dissolved in methanol (4 mL). An acetic acid (222 μL) was added to the resultant at room temperature, and then the mixture was stirred for 1 hour. The reaction mixture was concentrated under reduced pressure to obtain the title compound (compound No. 30: 108 mg).



1HNMR (CD3OD): 1.35-1.44 (m, 4H), 1.45-1.52 (m, 2H), 1.56-1.64 (m, 2H), 1.74-1.85 (m, 4H), 1.87-1.94 (m, 2H), 1.95 (s, 9H), 3.18 (t, 2H), 3.27 (t, 2H), 3.55 (t, 2H), 4.14 (t, 2H), 7.12 (d, 2H), 7.80 (d, 2H).


EXAMPLE 31
(Step 1) Synthesis of tert-butyl N-[N,N′-bis(tert-butoxycarbonyl)-N-[4-[[5-(N-tert-butoxycarbonylcarbamimidoyl)-2-pyridyl]oxy]butyl]carbamimidoyl]-N-(7-bromoheptyl) carbamate



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The title compound was obtained in the same manner as in the step 1 of Example 28.



1HNMR (CDCl3): 1.24-1.30 (m, 4H), 1.42-1.63 (m, 42H), 1.81-1.85 (m, 4H), 3.39 (t, 2H), 3.48 (t, 2H), 3.56 (m, 2H), 4.35 (t, 2H), 6.73 (t, 1H), 8.13 (d, 1H), 8.87 (d, 1H).


(Step 2) Synthesis of tert-butyl N-[N,N′-bis(tert-butoxycarbonyl)-N-[4-[[5-(N-tert-butoxycarbonylcarbamimidoyl)-2-pyridyl]oxy]butyl]carbamimidoyl]-N-[7-[[N,N′-bis(tert-butoxycarbonyl)carbamimidoyl]amino]heptyl]carbamate



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The title compound (compound No. 31) was obtained in the same manner as in the step 2 of Example 28.



1HNMR (CDCl3): 1.22-1.28 (m, 6H), 1.46-1.60 (m, 58H), 1.75-1.82 (m, 4H), 3.39 (m, 2H), 3.59 (m, 2H), 3.82 (t, 2H), 4.13 (t, 2H), 6.72 (d, 1H), 8.19 (d, 1H), 8.68 (s, 1H).


EXAMPLE 32
Synthesis of 6-(4-(3-(7-guanidinoheptyl)guanidino)butoxy)nicotinimidamide



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The title compound (compound No. 32) was obtained in the same manner as in Example 2.



1HNMR (CDCl3): 1.18-1.28 (m, 6H), 1.46-1.58 (m, 4H), 1.74 (m, 2H), 1.87 (m, 2H), 3.13-3.19 (m, 4H), 3.28 (m, 2H), 4.44 (m, 2H), 7.01 (br, 1H), 8.09 (br, 1H), 8.64 (s, 1H).


EXAMPLE 33
(Step 1) Synthesis of tert-butyl N-[N,N′-bis(tert-butoxycarbonyl)-N-[3-[5-(N-tert-butoxy carbonylcarbamimidoyl)benzofuran-2-yl]propyl]carbamimidoyl]-N-(7-bromoheptyl) carbamate



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The title compound was obtained in the same manner as in the step 1 of Example 28.



1HNMR (CDCl3): 1.25-1.56 (m, 44H), 1.84 (m, 2H), 2.12 (br, 2H), 2.82 (m, 2H), 3.38 (t, 2H), 3.49 (m, 2H), 3.62 (m, 2H), 6.45 (s, 1H), 7.40 (d, 1H), 7.72 (d, 1H), 8.05 (s, 1H).


(Step 2) Synthesis of tert-butyl N-[N,N′-bis(tert-butoxycarbonyl)-N-[3-[5-(N-tert-butoxy carbonylcarbamimidoyl)benzofuran-2-yl]propyl]carbamimidoyl]-N-[7-[[N,N′-bis(tert-butoxycarbonyl)carbamimidoyl]amino]heptyl]carbamate



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The title compound (compound No. 33) was obtained in the same manner as in the step 2 of Example 28.



1HNMR (CDCl3): 1.20-1.28 (m, 6H), 1.45-1.57 (m, 58H), 2.12 (m, 2H), 2.81 (t, 2H), 3.47 (t, 2H), 3.62 (t, 2H), 3.82 (t, 2H), 6.46 (s, 1H), 7.40 (d, 1H), 7.78 (d, 1H), 8.11 (s, 1H).


EXAMPLE 34
Synthesis of 2-(3-(3-(7-guanidinoheptyl)guanidino)propyl)benzofuran-5-carboximidamide



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The title compound (compound No. 34) was obtained in the same manner as in Example 2.



1HNMR (CDCl3): 1.30-1.42 (m, 6H), 1.55-1.62 (m, 4H), 2.05 (m, 2H), 2.93 (t, 2H), 3.30 (m, 2H), 3.10-3.18 (m, 4H), 6.73 (s, 1H), 7.64-7.66 (m, 2H), 8.02 (s, 1H).


EXAMPLE 35
Synthesis of tert-butyl N-[4-[4-[3-[4-[4-(N-tert-butoxycarbonylcarbamimidoyl)phenoxy]butyl]-2-(2,2,2-trifluoroacetyl)imino-imidazol-1-yl]butoxy]benzenecarboximidoyl]carbamate



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The title compound (compound No. 35) was obtained in the same manner as in Example 18.



1HNMR (CDCl3): 1.55 (s, 18H), 1.79 (tt, 4H), 1.97 (tt, 4H), 3.96 (t, 4H), 4.00 (t, 4H), 6.78 (s, 2H), 6.89 (d, 4H), 7.81 (d, 4H).


EXAMPLE 36
Synthesis of hydrochloride salt of 4-[4-[3-[4-(4-carbamimidoylphenoxy)butyl]-2-imino-imidazol-1-yl]butoxy]benzamidine



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The tert-butyl N-[4-[4-[3-[4-[4-(N-tert-butoxycarbonylcarbamimidoyl)phenoxy]butyl]-2-(2,2,2-trifluoroacetyl)imino-imidazol-1-yl]butoxy]benzenecarboximidoyl]carbamate (666 mg) obtained in Example 35 was dissolved in methanol (4 mL). Hydrogen chloride (4M in dioxane solution) (10 mL) was added to the solution at room temperature. The reaction mixture was stirred at 50° C. overnight. The reaction mixture was cooled to room temperature, and then concentrated under reduced pressure to obtain the title compound (compound No. 36: 536 mg).


Melting point (mp): 178-180° C.


EXAMPLE 37
(Step 1) Synthesis of N-[1,3-bis(4-bromobutyl)imidazolidin-2-ylidene]nitramide



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N-imidazolidin-2-ylidene-nitramide (1.5 g) was dissolved in acetonitrile (15 mL). Potassium carbonate (4.77 mg) and 1,4-dibromobutane (9.96 g) were added to the solution at room temperature. The reaction mixture was stirred at 80° C. overnight. The reaction mixture was cooled to room temperature, and then was concentrated under reduced pressure. Water was added to the resulting residue, and then the mixture was subjected to extraction with ethyl acetate. The resultant organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography to obtain the title compound (83 mg, in a yield of 1.8%).



1HNMR (CDCl3): 1.74-1.83 (m, 4H), 1.85-1.94 (m, 4H), 3.33 (t, 4H), 3.44 (t, 4H), 3.75 (s, 4H).


(Step 2) Synthesis of tert-butyl N-[4-[4-[3-[4-[4-(N-tert-butoxycarbonylcarbamimidoyl) phenoxy]butyl]-2-nitroimino-imidazolidin-1-yl]butoxy]benzenecarboximidoyl]carbamate



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N-[1,3-bis(4-bromobutyl)imidazolidin-2-ylidene]nitramide (84 mg) obtained in the step 1 was dissolved in acetonitrile (3 mg). Potassium carbonate (115 mg) and tert-butyl N-(4-hydroxybenzenecarboximidoyl)carbamate (149 mg) were added to the solution at room temperature. The reaction mixture was stirred at 80° C. overnight. The reaction mixture was cooled to room temperature and then was concentrated under reduced pressure. Water was added to the resulting residue, and the mixture was subjected to extraction with ethyl acetate. The resultant organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography to obtain the title compound (compound No. 37: 38 mg, in a yield of 25.7%).



1HNMR (CDCl3): 1.55-1.59 (m, 22H), 1.17-1.85 (m, 8H), 3.37 (t, 4H), 4.00-4.04 (m, 4H), 6.89 (d, 4H), 7.81 (d, 4H).


EXAMPLE 38
Synthesis of hydrochloride salt of 4-[4-[3-[4-(4-carbamimidoylphenoxy)butyl]-2-nitroimino-imidazolidin-1-yl]butoxy]benzamidine



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The title compound (compound No. 38) was obtained in the same manner as in Example 2.



1HNMR (CD3OD): 1.31 (t, 4H), 1.82-1.88 (m, 8H), 3.20 (dd, 4H), 4.11-4.16 (m, 4H), 7.13 (d, 4H), 7.86 (d, 4H).


EXAMPLE 39
Synthesis of tert-butyl N-[4-[3-[3-[4-[4-(N-tert-butoxycarbonylcarbamimidoyl)phenoxy]butyl]-2-(2,2,2-trifluoroacetyl)imino-imidazol-1-yl]propoxy]benzenecarboximidoyl]carbamate



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The title compound (compound No. 39) was obtained in the same manner as in Example 18.



1HNMR (CDCl3): 1.55 (s, 18H), 1.76-1.84 (m, 2H), 1.96 (tt, 2H), 2.25 (tt, 2H), 3.94-4.04 (m, 6H), 4.12 (t, 2H), 6.72 (dd, 2H), 6.88 (dd, 4H), 7.81 (d, 4H).


EXAMPLE 40
Synthesis of hydrochloride salt of 4-[4-[3-[3-(4-carbamimidoylphenoxy)propyl]-2-imino-imidazol-1-yl]butoxy]benzamidine



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The title compound (compound No. 40) was obtained in the same manner as in Examples 19 and 20.



1HNMR (CD3OD): 1.82-2.00 (m, 4H), 2.29 (tt, 2H), 3.97 (t, 2H), 4.11-4.22 (m, 6H), 6.96 (dd, 2H), 7.14 (dd, 4H), 7.79 (d, 2H), 7.81 (d, 2H).


EXAMPLE 41
Synthesis of tert-butyl N-[N,N′-bis(tert-butoxycarbonyl)-N-[3-[4-(N-tert-butoxy carbonylcarbamimidoyl)phenoxy]propyl]carbamimidoyl]-N-[3-[4-(N-tert-butoxycarbonyl carbamimidoyl)phenoxy]propyl]carbamate



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The title compound (compound No. 41) was obtained in the same manner as in Example 9.



1HNMR (CDCl3): 1.44-1.59 (m, 45H), 2.13 (dt, 4H), 3.69 (t, 4H), 3.99 (t, 4H), 6.81 (d, 4H), 7.74 (d, 4H).


EXAMPLE 42
Synthesis of hydrochloride salt of 4-[3-[[N-[3-(4-carbamimidoylphenoxy)propyl]carbamimidoyl]amino]propoxy]benzamidine



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The title compound (compound No. 42) was obtained in the same manner as in Example 2.



1HNMR (CD3OD): 2.12 (tt, 4H), 3.41-3.51 (m, 4H), 4.19 (t, 4H), 7.16 (d, 4H), 7.79 (d, 4H).


EXAMPLE 43
(Step 1) Synthesis of 6-(3-((tert-butyldimethylsilyl)oxy)propoxy)pyridazine-3-carbonitrile



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3-((tert-butyldimethylsilyl)oxy)propan-1-ol (2.5 g) was dissolved in tetrahydrofuran (30 mL). At 0° C., sodium hydride (0.58 g) was added to the solution, and then 6-chloro-pyridazine-3-carbonitrile (1.7 g) was added thereto. The mixture was stirred for 18 hours at room temperature, and then saturated aqueous ammonium chloride solution was added thereto. The resultant was subjected to extraction with ethyl acetate, and the resultant organic layer was concentrated. The resulting residue was purified by silica gel column chromatography to obtain the title compound (2.2 g).



1HNMR (CDCl3): 0.037 (s, 6H), 0.87 (s, 9H), 2.04 (m, 2H), 3.79 (t, 2H), 4.71 (t, 2H), 7.04 (d, 1H), 7.65 (d, 1H).


Step 2
Synthesis of tert-butyl ((6-(3-hydroxypropoxy)pyridazin-3-yl)(imino)methyl)carbamate



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The 6-(3-((tert-butyldimethylsilyl)oxy)propoxy)pyridazine-3-carbonitrile (0.59 g) obtained in the step 1 was dissolved in tetrahydrofuran (6 mL). Lithium bis(trimethylsilyl)amide (2 mL, 1.3M in tetrahydrofuran solution) was added to the solution at room temperature. The mixture was stirred for 2 hours at room temperature, and then hydrogen chloride (3 mL, in 4M 1,4-dioxane solution) was added thereto. The resultant was stirred for 2 hours at room temperature, and then the solvent was distilled off therefrom. The obtained crude product was dissolved in N, N-dimethylformamide (4 mL). Triethylamine (1.0 g) and di-tert-butyl dicarbonate (0.65 g) were added to the solution. The mixture was stirred for 3 hours, and then saturated aqueous ammonium chloride solution was added thereto. The mixture was subjected to extraction with ethyl acetate, and the resultant organic layer was concentrated. The obtained crystal was washed with hexane to obtain the title compound (0.40 g).



1HNMR (CDCl3): 1.55 (s, 9H), 2.11 (m, 2H), 3.80 (t, 2H), 4.74 (t, 2H), 7.03 (d, 1H), 8.41 (d, 1H).


(Step 3) Synthesis of tert-butyl N-[-N,N′-bis(tert-butoxycarbonyl)-N-[3-[6-(N-tert-butoxycarbonylcarbamimidoyl)pyridazin-3-yl]oxypropyl]carbamimidoyl]-N-(7-bromo heptyl)carbamate



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The title compound was obtained in the same manner as in the step 1 of Example 28.



1HNMR (CDCl3): 1.25-1.55 (m, 42H), 1.62 (m, 2H), 1.81 (m, 2H), 2.20 (m, 2H), 3.38 (t, 2H), 3.42 (m, 2H), 3.70 (m, 2H), 4.60 (t, 2H), 7.01 (d, 1H), 8.39 (d, 1H).


(Step 4) Synthesis of tert-butyl N-[N,N′-bis(tert-butoxycarbonyl)-N-[3-[6-(N-tert-butoxycarbonylcarbamimidoyl)pyridazin-3-yl]oxypropyl]carbamimidoyl]-N-[7-[[N,N′-bis (tert-butoxycarbonyl)carbamimidoyl]amino]heptyl]carbamate



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The title compound (compound No. 43) was obtained in the same manner as in the step 2 of Example 11.



1HNMR (CDCl3): 1.44-1.65 (m, 64H), 2.22 (m, 2H), 3.48 (m, 2H), 3.71 (t, 2H), 3.85 (m, 2H), 4.61 (t, 2H), 7.01 (d, 1H), 8.38 (d, 1H).


EXAMPLE 44
Synthesis of hydrochloride salt 6-(3-(3-(7-guanidinoheptyl)guanidino)propoxy) pyridazine-3-carboxamidine



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The title compound (compound No. 44) was obtained in the same manner as in Example 2.


Melting point (mp) 242-249° C.


EXAMPLE 45
(Step 1) synthesis of 6-(4-bromobutoxy)nicotinonitrile



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6-(4-hydroxybutoxy)nicotinonitrile (2.47 g) was dissolved in tetrahydrofuran (30 mL). Carbon tetrabromide (5.6 g) and triphenylphosphine (4.4 g) were added to the solution at 0° C. The mixture was stirred for 23 hours at room temperature, and then saturated aqueous sodium hydrogen carbonate solution was added thereto. The resultant was subjected to extraction with ethyl acetate, the solvent was distilled off therefrom, and then the resultant residue was purified by silica gel column chromatography to obtain the title compound (2.8 g).



1HNMR (CDCl3): 1.93-2.04 (m, 4H), 3.45 (d, 2H), 4.38 (t, 2H), 6.78 (d, 1H), 7.76 (dd, 1H), 8.45 (d, 1H).


(Step 2) Synthesis of tert-butyl ((6-(4-bromobutoxy)pyridin-3-yl)(imino)methyl) carbamate



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6-(4-bromobutoxy)nicotinonitrile (2.8 g) obtained in the step 1 was dissolved in tetrahydrofuran (30 mL). Lithium bis(trimethylsilyl)amide (10 mL, in 1.3M tetrahydrofuran solution) was added to the solution at 0° C. The resultant was stirred for 4 hours at room temperature, and then cooled to 0° C., followed by adding methanol (10 mL) and hydrogen chloride (10 mL, in 4M 1,4-dioxane solution) thereto. The resultant was stirred for 30 minutes at 0° C., and then the solvent was distilled off therefrom. The resultant crude product was dissolved in N, N-dimethylformamide (30 mL), and triethylamine (5.6 g) and di-tert-butyl dicarbonate (3.6 g) were added thereto. The resultant was stirred for 1.5 hours and then purified by silica gel column chromatography to obtain the title compound (4.0 g).



1HNMR (CDCl3): 1.55 (s, 9H), 1.90-2.04 (m, 4H), 3.46 (d, 2H), 4.36 (t, 2H), 6.73 (d, 1H), 8.10 (d, 1H), 8.57 (s, 1H).


(Step 3) Synthesis of di-tert-butyl (((((2-((2,2,2-trifluoroacetyl)imino)-1H-imidazole-1,3(2H)-diyl)bis(butane-4,1-diyl))bis(oxy))bis(pyridine-6,3-diyl))bis(iminomethylene)) dicarbamate



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The tert-butyl ((6-(4-bromobutoxy)pyridin-3-yl)(imino)methyl) carbamate (0.74 g) obtained in the step 2 was dissolved in N, N-dimethylformamide (3 mL). N-(1,3-dihydro-2H-imidazol-2-ylidene)-2,2,2-trifluoroacetamide (0.14 g), sodium iodide (0.36 g), and potassium carbonate (0.28 g) were added to the solution. The resultant was stirred for 9 hours at 60° C., and then water was added thereto. The resultant was subjected to extraction with ethyl acetate, and the resultant organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (compound No. 45: 0.41 g).



1HNMR (CDCl3): 1.51 (s, 18H), 1.75 (m, 4H), 1.87 (m, 4H), 3.89 (m, 4H), 4.31 (m, 4H), 6.65 (d, 2H), 6.75 (s, 2H), 8.07 (d, 2H), 8.55 (s, 2H).


EXAMPLE 46
Synthesis of trifluoroacetic acid salt of N-(1,3-bis(4-((5-carbamimidoylpyridin-2-yl) oxy)butyl)-1,3-dihydro-2H-imidazol-2-ylidene)-2,2,2-trifluoroacetamide



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The di-tert-butyl (((((2-((2,2,2-trifluoroacetyl)imino)-1H-imidazole-1,3(2H)-diyl) bis(butane-4,1-diyl))bis(oxy))bis(pyridine-6,3-diyl))bis(iminomethylene)) dicarbamate (0.41 g) obtained in the step 3 of Example 45 was dissolved in dichloromethane (3 mL). Trifluoroacetic acid (1.5 mL) was added to the solution at room temperature, and then the mixture was stirred for 17 hours at room temperature. The solvent in the reaction mixture was distilled off therefrom to obtain the title compound (compound No. 46: 0.20 g).



1HNMR (CDCl3): 1.77 (m, 4H), 1.91 (m, 4H), 3.93 (t, 4H), 4.41 (t, 4H), 6.93 (d, 2H), 7.25 (s, 2H), 8.00 (d, 2H), 8.59 (s, 2H).


EXAMPLE 47
(Step 1) Synthesis of tert-butyl N-[5-(hydroxymethyl)thiophene-3-carboximidoyl]carbamate



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5-[[tert-butyl(dimethyl)silyl]oxymethyl]thiophene-3-carbonitrile (2 g) was dissolved in tetrahydrofuran (20 mL). Lithium bis(trimethylsilyl)amide (1.3M in tetrahydrofuran solution) (9.1 mL) was added to the solution at room temperature. The mixture was stirred for 1 hour at the same temperature, and then hydrogen chloride (4M in dioxane solution) (20 mL) and methanol (20 mL) were added thereto under ice-cooling. The reaction mixture was stirred for 2 hours at room temperature. The reaction mixture was concentrated under reduced pressure, and the resulting residue was dissolved in N, N-dimethylformamide (20 mL). Triethylamine (4.79 g) and di-tert-butyl dicarbonate (5.16 g) were added to the solution under ice-cooling. The mixture was stirred for 4 hours at room temperature. Water was added to the reaction mixture, and the mixture was subjected to extraction with ethyl acetate. The resultant organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography to obtain the title compound (392 mg, in a yield of 19.4%).



1HNMR (CDCl3): 1.54 (s, 9H), 4.81 (s, 2H), 7.38 (s, 1H), 7.92 (s, 1H).


(Step 2) Synthesis of tert-butyl N-[5-(bromomethyl)thiophene-3-carboximidoyl]carbamate



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The tert-butyl N-[5-(hydroxymethyl)thiophene-3-carboximidoyl]carbamate (134 mg) obtained in the step 1 was dissolved in tetrahydrofuran (3 mL). Triphenylphosphine (150 mg) and carbon tetrabromide (190 mg) were added to the solution under ice-cooling. The reaction mixture was stirred for 4 hours at room temperature. The reaction mixture was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography to obtain the title compound (81 mg, in a yield of 16.7%).



1HNMR (CDCl3): 1.54 (s, 9H), 4.67 (s, 2H), 7.51 (d, 1H), 7.97 (d, 1H).


(Step 3) Synthesis of tert-butyl N-[5-(2-hydroxyethoxymethyl)thiophene-3-carboximidoyl]carbamate



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The tert-butyl N-[5-(bromomethyl)thiophene-3-carboximidoyl]carbamate (81 mg) obtained in the step 2 was dissolved in ethylene glycol (2 mL) and N, N-dimethylformamide (2 mL), and potassium carbonate (70 mg) was added thereto at room temperature. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain the title compound (31 mg, in a yield of 40.8%).



1HNMR (CDCl3): 1.55 (s, 9H), 3.60 (t, 2H), 3.76 (t, 2H), 4.69 (s, 2H), 7.41 (s, 1H), 7.93 (s, 1H).


(Step 4) Synthesis of tert-butyl N-[N,N′-bis(tert-butoxycarbonyl)-N-[2-[[4-(N-tert-butoxycarbonylcarbamimidoyl)-2-thienyl]methoxy]ethyl]carbamimidoyl]-N-(7-bromo heptyl)carbamate



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The title compound was obtained in the same manner as in the step 1 of Example 28.



1HNMR (CDCl3): 1.12-1.25 (m, 4H), 1.33-1.40 (m, 2H), 1.43-1.60 (m, 38H), 1.75-1.86 (m, 4H), 3.38 (t, 2H), 3.72 (t, 2H), 3.87 (t, 2H), 4.63 (s, 2H), 7.49 (s, 1H), 8.07 (s, 1H).


(Step 5) Synthesis of tert-butyl N-[N,N′-bis(tert-butoxycarbonyl)-N-[2-[[4-(N-tert-butoxycarbonylcarbamimidoyl)-2-thienyl]methoxy]ethyl]carbamimidoyl]-N-[7-[[N,N′-bis (tert-butoxycarbonyl)carbamimidoyl]-tert-butoxycarbonyl-amino]heptyl]carbamate



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The title compound (compound No. 47) was obtained in the same manner as in the step 2 of Example 28.



1HNMR (CDCl3): 1.01-1.16 (m, 6H), 1.43-1.62 (m, 58H), 3.34-3.42 (m, 2H), 3.71-3.75 (m, 2H), 3.76-3.83 (m, 2H), 3.84-3.91 (m, 2H), 4.62 (s, 2H), 7.54 (s, 1H), 8.16 (s, 1H).


EXAMPLE 48
Synthesis of hydrochloride salt of 5-[2-[[N-(7-guanidinoheptyl)carbamimidoyl]amino]ethoxymethyl]thiophene-3-carboxamidine



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The title compound (compound No. 48) was obtained in the same manner as in Example 2.



1HNMR (CD3OD): 1.36-1.45 (m, 6H), 1.53-1.67 (m, 4H), 3.11-3.23 (m, 6H), 3.41-3.50 (m, 2H), 3.65-3.72 (m, 2H), 7.52 (d, 1H), 8.37 (d, 1H).


EXAMPLE 49
(Step 1) Synthesis of ethyl 2-(5-hydroxypent-1-ynyl)thiazole-4-carboxylate



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Ethyl 2-bromothiazole-4-carboxylate (2.32 g) was dissolved in diisopropylamine. Pent-4-yn-1-ol (1.07 g), bis(triphenylphosphine)palladium (II) dichloride (344 mg), and copper iodide (56 mg) were added to the solution at room temperature. The mixture was stirred at 70° C. for 6 hours. The reaction mixture was cooled to room temperature, and then filtered with Celite (trademark). Water was added to the filtrate, and the mixture was subjected to extraction with ethyl acetate. The resultant organic layer was dried over anhydrous sodium sulfate and then filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography to obtain a mixture containing the title compound and an unknown structure product (992 mg).



1HNMR (CDCl3): 1.41 (t, 3H), 1.88 (dt, 2H), 2.61 (t, 2H), 3.80 (dd, 2H), 4.44 (dd, 2H), 8.11 (s, 1H)


(Step 2) Synthesis of ethyl 2-[5-[tert-butyl(dimethyl)silyl]oxypent-1-ynyl]thiazole-4-carboxylate



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The mixture (992 mg) containing ethyl 2-(5-hydroxypent-1-ynyl)thiazole-4-carboxylate obtained in the step 1 was dissolved in dichloromethane (10 mL). Triethylamine (1.05 g), tert-butyldimethylsilyl chloride (750 mg), N,N-dimethyl-4-aminopyridine (50 mg) were added to the solution under ice-cooling. The mixture was stirred for 2 hours at room temperature. Water was added to the reaction mixture, and the mixture was subjected to extraction with ethyl acetate. The resultant organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography to obtain the title compound (817 mg, in a yield of 55.9%).



1HNMR (CDCl3): 0.07 (s, 6H), 0.90 (s, 9H), 1.41 (t, 3H), 1.83 (dt, 2H), 2.56 (t, 2H), 3.73 (t, 2H), 4.42 (dd, 2H), 8.10 (s, 1H).


(Step 3) Synthesis of 2-[5-[tert-butyl(dimethyl)silyl]oxypent-1-ynyl]thiazole-4-carboximidic acid



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The ethyl 2-[5-[tert-butyl(dimethyl)silyl]oxypent-1-ynyl]thiazole-4-carboxylate (1 g) obtained in the step 2 was dissolved in methanol (6 mL) in a sealed tube, and ammonia (7M in methanol solution) (4 mL) was added thereto at room temperature. The reaction container was sealed and heated to 80° C. The reaction mixture was stirred at the same temperature overnight. The reaction mixture was cooled to room temperature, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound (862 mg, in a yield of 91.8%).



1HNMR (CDCl3): 0.07 (s, 6H), 0.91 (s, 9H), 1.85 (dt, 2H), 2.59 (t, 2H), 3.74 (t, 2H), 8.09 (s, 1H).


(Step 4) Synthesis of tert-butyl N-[2-(5-hydroxypent-1-ynyl)thiazole-4-carboximidoyl]carbamate



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The 2-[5-[tert-butyl(dimethyl)silyl]oxypent-1-ynyl]thiazole-4-carboximidic acid (264 mg) obtained in the step 3 was dissolved in dichloromethane (4 mL). Trimethyloxonium tetrafluoroborate (Me3OBF4) (144 mg) was added to the solution under ice-cooling. The reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure and the resulting residue was dissolved in methanol (2 mL). Ammonia (7M in methanol solution) (4 mL) was added to the resultant under ice-cooling. The mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, the resulting residue was dissolved in N, N-dimethylformamide (3 mL), and then trifluoroacetic acid (329 mg) and di-tert-butyl dicarbonate (266 mg) were added thereto under ice-cooling. The resultant was stirred for 5 hours at room temperature. Water was added to the reaction mixture, and the mixture was subjected to extraction with ethyl acetate. The resultant organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography to obtain the title compound (35.4 mg, in a yield of 10.2%).



1HNMR (CDCl3): 1.55 (s, 9H), 1.91 (dt, 2H), 2.64 (t, 2H), 3.82 (dd, 2H), 8.29 (s, 1H).


(Step 5) Synthesis of tert-butyl N—[N,N′-bis(tert-butoxycarbonyl)-N-[5-[4-(N-tert-butoxy carbonylcarbamimidoyl)thiazol-2-yl]pent-4-ynyl]carbamimidoyl]-N-(7-bromoheptyl) carbamate



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The title compound was obtained in the same manner as in the step 1 of Example 28.



1HNMR (CDCl3): 1.24-1.38 (m, 4H), 1.45-1.56 (m, 36H), 1.62-1.72 (m, 4H), 1.83 (dt, 2H), 1.98-2.05 (m, 2H), 2.56 (t, 2H), 3.39 (t, 2H), 3.51 (dd, 2H), 3.67 (dd, 2H), 8.28 (s, 1H).


(Step 6) Synthesis of tert-butyl N—[N,N′-bis(tert-butoxycarbonyl)-N-[5-[4-(N-tert-butoxy carbonylcarbamimidoyl)thiazol-2-yl]pent-4-ynyl]carbamimidoyl]-N-[7-[[N,N′-bis(tert-butoxycarbonyl)carbamimidoyl]-tert-butoxycarbonyl-amino]heptyl]carbamate



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The title compound (compound No. 49) was obtained in the same manner as in the step 2 of Example 28.



1HNMR (CDCl3): 1.23-1.33 (m, 6H), 1.45-1.56 (m, 54H), 1.60-1.72 (m, 6H), 2.56 (t, 2H), 3.49 (dd, 2H), 3.66 (dd, 2H), 3.87 (dd, 2H), 8.28 (s, 1H).


EXAMPLE 50
Synthesis of hydrochloride salt of 2-[5-[[N-(7-guanidinoheptyl)carbamimidoyl]amino]pent-1-ynyl]thiazole-4-carboxamidine



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The title compound (compound No. 50) was obtained in the same manner as in Example 2.



1HNMR (CD3OD): 1.36-1.46 (m, 6H), 1.54-1.68 (m, 4H), 1.93 (dt, 2H), 2.66 (t, 2H), 3.12-3.24 (m, 6H), 8.66 (s, 1H).


EXAMPLE 51
(Step 1) Synthesis of tert-butyl N-[4-[4-[2-(2,2,2-trifluoroacetyl)imino-1H-imidazol-3-yl]butoxy]benzenecarboximidoyl]carbamate



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Tert-butyl N-[4-(4-bromobutoxy)benzenecarboximidoyl]carbamate (3.00 g) was dissolved in acetonitrile (50 mL) and benzene (25 mL). N-(1,3-dihydroimidazol-2-ylidene)-2,2,2-trifluoro-acetamide (4.34 g), potassium carbonate (1.68 g) and sodium iodide (1.33 g) were sequentially added to the solution, and the mixture was stirred at 50° C. overnight. Then, the reaction mixture was cooled to room temperature, water was added thereto, and the resultant was subjected to extraction with chloroform. The resultant organic layer was dried over anhydrous magnesium sulfate, and then filtered. The filtrate was concentrated under reduced pressure, and then the resulting residue was purified by silica gel column chromatography to obtain the title compound (0.93 g, in a yield of 25%).



1H NMR (CDCl3): 1.55 (s, 9H), 1.76-1.87 (m, 2H), 2.01 (tt, 2H), 4.03-4.14 (m, 4H), 6.70 (d, 1H), 6.81 (d, 1H), 6.90 (d, 2H), 7.83 (d, 2H).


(Step 2) Synthesis of tert-butyl N-[4-[4-[3-[7-[[N,N′-bis(tert-butoxycarbonyl) carbamimidoyl]amino]heptyl]-2-(2,2,2-trifluoroacetyl)imino-imidazol-1-yl]butoxy]benzenecarboximidoyl]carbamate



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The tert-butyl N-[4-[4-[2-(2,2,2-trifluoroacetyl)imino-1H-imidazol-3-yl]butoxy]benzenecarboximidoyl]carbamate (491.3 mg) obtained in the step 1 and tert-butyl N-[(7-bromoheptylamino)-(tert-butoxycarbonylamino)methylene]carbamate (0.68 g) were dissolved in acetonitrile (10 mL) and benzene (5 mL). Potassium carbonate (0.18 g) was added to the solution, and the mixture was stirred at 50° C. for 2 days. Then, the reaction mixture was cooled to room temperature, and filtered with Celite (trademark). The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain the title compound (compound No. 51: 278 mg, in a yield of 32%).



1H NMR (CDCl3): 1.23-1.39 (m, 6H), 1.45-1.63 (m, 29H), 1.68-1.86 (m, 4H), 1.97 (tt, 2H), 3.81-3.91 (m, 4H), 3.95 (t, 2H), 4.02 (t, 2H), 6.74 (d, 1H), 6.77 (d, 1H), 6.88 (d, 2H), 7.83 (d, 2H).


EXAMPLE 52
Synthesis of hydrochloride salt of 4-[4-[3-(7-guanidinoheptyl)-2-imino-imidazol-1-yl]butoxy]benzamidine



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The tert-butyl N-[4-[4-[3-[7-[[N,N′-bis(tert-butoxycarbonyl)carbamimidoyl]amino]heptyl]-2-(2,2,2-trifluoroacetyl)imino-imidazol-1-yl]butoxy]benzene carboximidoyl]carbamate (278 mg) obtained in Example 51 was dissolved in methanol (10 mL). Hydrogen chloride in a 1,4-dioxane solution (4M, 10 mL) was added to the resultant at room temperature, and the mixture was stirred at 50° C. overnight. The reaction mixture was cooled to room temperature and was concentrated under reduced pressure to obtain the title compound (compound No. 52: 230 mg, quantitative).



1H NMR (CD3OD): 1.33-1.46 (m, 6H), 1.59 (tt, 2H), 1.76 (tt, 2H), 1.82-2.02 (m, 4H), 3.17 (t, 2H), 3.88 (t, 2H), 3.98 (t, 2H), 4.15 (t, 2H), 6.98 (d, 1H), 7.01 (d, 1H), 7.14 (d, 2H), 7.80 (d, 2H).


EXAMPLE 53
(Step 1) Synthesis of N-[1,3-bis[3-hydroxypropyl]-1,3-dihydro-2H-imidazol-2-ylidene]-2,2,2-trifluoroacetamide



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N-[1,3-dihydro-2H-imidazol-2-ylidene]-2,2,2-trifluoroacetamide (0.31 g) was dissolved in acetonitrile (10 mL). Potassium carbonate (0.75 g) and 3-bromo-1-propanol (0.75 g) were added to the solution at room temperature. The reaction mixture was heated to 60° C., and stirred at the same temperature overnight, followed by pouring the resultant into water to conduct extraction with ethyl acetate. The resultant organic layer was washed with saturated saline solution, and then dried over anhydrous sodium sulfate. The organic layer was concentrated and the resulting residue was purified by silica gel column chromatography to obtain the title compound (0.32 g).



1H NMR (CD3OD): 1.93 (tt, 4H), 3.53 (t, 4H), 3.98 (t, 4H), 7.21 (s, 2H).


(Step 2) Synthesis of tert-butyl N-[3-bromo-4-[3-[3-[3-[2-bromo-4-(N-tert-butoxy carbonylcarbamimidoyl)phenoxy]propyl]-2-(2,2,2-trifluoroacetyl)imino-imidazol-1-yl]propoxy]benzenecarboximidoyl]carbamate



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N-[1,3-bis[3-hydroxypropyl]-1,3-dihydro-2H-imidazol-2-ylidene]-2,2,2-trifluoro acetamide (0.32 g) obtained in the step 1 was dissolved in toluene (30 mL). At room temperature, tetrahydrofuran (10 mL) was added to the solution, and tert-butyl N-(3-bromo-4-hydroxy-benzenecarboximidoyl)carbamate (0.76 g) was added thereto. At room temperature, tributylphosphine (0.90 g) and 1,1′-(azodicarbonyl)dipiperidine (1.10 g) were added to the mixture. The mixture was stirred overnight, and then the resultant was poured into water to conduct extraction with ethyl acetate. The resultant organic layer was washed with saturated saline solution, dried over anhydrous sodium sulfate, and then filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography to obtain the title compound (compound No. 53: 0.40 g).



1H NMR (CD3OD): 1.51 (s, 18H), 2.29 (tt, 4H), 4.10 (t, 4H), 4.15 (t, 4H), 7.04 (d, 2H), 7.79 (dd, 2H), 8.07 (d, 2H).


EXAMPLE 54
Synthesis of hydrochloride salt of 3-bromo-4-[3-[3-[3-(2-bromo-4-carbamimidoyl-phenoxy)propyl]-2-imino-imidazol-1-yl]propoxy]benzamidine



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The title compound (compound No. 54) was obtained in the same manner as in Example 52.


Melting point: 193-197° C.


EXAMPLE 55
Synthesis of N-[1,3-bis[3-[4-[N′-hydroxycarbamimidoyl]phenoxy]propyl]-1,3-dihydro-2H-imidazol-2-ylidene]-2,2,2-trifluoroacetamide



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N-[1,3-bis[3-[4-cyanophenoxy]propyl]-1,3-dihydro-2H-imidazol-2-ylidene]-2,2,2-trifluoroacetamide (0.60 g) was dissolved in N,N-dimethyl sulfoxide (6 mL). A 50% hydroxylamine solution (0.13 g) was added to the solution at room temperature. The reaction mixture was heated to 50° C. and stirred at the same temperature overnight. A 2N aqueous sodium hydroxide solution was poured into the reaction mixture, and the mixture was subjected to extraction with tetrahydrofuran. The resultant organic layer was dried over anhydrous sodium sulfate and then filtered. The filtrate was concentrated under reduced pressure, and the concentrated residue was washed sequentially with water, ethyl acetate, and hexane to obtain the title compound (compound No. 55: 0.39 g).


Melting point: 187-201° C.


EXAMPLE 56
(Step 1) Synthesis of tert-butyl N-[4-[3-[3-[4-(N-tert-butoxycarbonylcarbamimidoyl) phenoxy]propylcarbamothioylamino]propoxy]benzenecarboximidoyl]carbamate



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Tert-butyl N-[4-(3-aminopropoxy)benzenecarboximidoyl]carbamate (445 mg) was dissolved in dichloromethane (5 mL). Triethylamine (273 mg) and tert-butyl N-[4-(3-isothiocyanatopropoxy)benzenecarboximidoyl]carbamate (389 g) were added to the solution at room temperature. The mixture was stirred at the same temperature for 3 hours, water was added to the reaction mixture, and then the resultant was subjected to extraction with chloroform. The resultant organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography to obtain the title compound (767 mg, in a yield of 91.7%).



1H NMR (CDCl3): 1.55 (s, 18H), 2.03-2.10 (m, 4H), 3.57-3.73 (m, 4H), 4.04 (t, 4H), 6.79 (d, 4H), 7.70 (t, 4H).


(Step 2) Synthesis of tert-butyl N-[4-[3-[(Z)-[[3-[4-(N-tert-butoxycarbonylcarbamimidoyl) phenoxy]propylamino]-methylsulfanyl-methylene]amino]propoxy]benzenecarboximidoyl]carbamate



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The tert-butyl N-[4-[3-[3-[4-(N-tert-butoxycarbonylcarbamimidoyl)phenoxy]propylcarbamothioylamino]propoxy]benzenecarboximidoyl]carbamate (767 mg) obtained in the step 1 was dissolved in acetone (10 mL). Potassium carbonate (253 mg) and methyl iodide (259 mg) were added to the solution under ice-cooling. The reaction mixture was warmed to room temperature and stirred at the same temperature for 4 hours. Water was added to the reaction mixture, and the mixture was subjected to extraction with ethyl acetate. The resultant organic layer was dried over anhydrous sodium sulfate, filtered, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound (566 mg, in a yield of 72%).



1H NMR (CDCl3): 1.55 (s, 18H), 2.00-2.09 (m, 4H), 2.33 (s, 3H), 3.39-3.51 (m, 4H), 4.07 (dd, 4H), 6.86 (d, 4H), 7.77 (d, 4H).


(Step 3) Synthesis of tert-butyl N-[N,N′-bis[3-[4-(N-tert-butoxycarbonylcarbamimidoyl) phenoxy]propyl]carbamimidoyl]-N-methyl-carbamate



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The tert-butyl N-[4-[3-[(Z)-[[3-[4-(N-tert-butoxycarbonylcarbamimidoyl) phenoxy]propylamino]-methylsulfanyl-methylene]amino]propoxy]benzenecarboximidoyl]carbamate (250 mg) obtained in the step 2 was dissolved in tetrahydrofuran (4 mL). Triethylamine (118 mg), silver trifluoromethanesulfonate (120 mg), and methylamine (2M in tetrahydrofuran solution 253 mL) were added to the resultant under ice-cooling. The reaction mixture was warmed to room temperature and stirred at the same temperature overnight. The reaction mixture was filtered, and then concentrated under reduced pressure.


The resulting residue was dissolved in N, N-dimethylformamide (4 mL), and triethylamine (197 mg) and di-tert-butyl dicarbonate (255 mg) were added thereto under ice-cooling. The reaction mixture was warmed to room temperature and stirred at the same temperature overnight. Water was added to the reaction mixture, and the mixture was subjected to extraction with ethyl acetate. The resultant organic layer was dried over anhydrous sodium sulfate, filtered, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound (compound No. 56: 12 mg, in a yield of 3.7%).



1H NMR (CDCl3): 1.37-1.69 (m, 36H), 2.00-2.07 (m, 4H), 2.76 (s, 3H), 3.27-3.36 (m, 4H), 3.99-4.08 (m, 4H), 6.79-6.87 (m, 4H), 7.33-7.41 (m, 2H), 7.72 (d, 2H).


EXAMPLE 57
Synthesis of hydrochloride salt of 4-[3-[[N-[3-(4-carbamimidoylphenoxy)propyl]-N′-methyl-carbamimidoyl]amino]propoxy]benzamidine



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The title compound (compound No. 57) was obtained in the same manner as in Example 2.


Melting point: 219-220° C.


EXAMPLE 58
(Step 1) Synthesis of tert-butyl N-[N,N′-bis(tert-butoxycarbonyl)carbamimidoyl]-N-[5-[[N,N′-bis(tert-butoxycarbonyl)carbamimidoyl]amino]pentyl]carbamate



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Tert-butyl N-[[tert-butoxycarbonylamino]-[5-hydroxypentylamino]methylene]carbamate (2.61 g) was dissolved in toluene (50 mL). 1,2,3-tris(tert-butoxycarbonyl)guanidine (4.11 g) was added to the solution at room temperature. Triphenylphosphine (3.02 g) and bis(2-methoxyethyl)azodicarboxylate (2.74 g) were added to the mixture at room temperature. The resultant was stirred overnight and then poured into water to conduct extraction with ethyl acetate. The resultant organic layer was washed with saturated saline solution, dried over anhydrous sodium sulfate, and then concentrated, followed by purifying the resulting residue by silica gel column chromatography to obtain the title compound (2.59 g).



1H NMR (CDCl3): 1.30-1.74 (m, 51H), 3.40 (q, 2H), 3.77 (t, 2H).


(Step 2) Synthesis of tert-butyl N-[N,N′-bis(tert-butoxycarbonyl)-N-[4-[4-(N-tert-butoxycarbonylcarbamimidoyl)phenoxy]butyl]carbamimidoyl]-N-[5-[[N,N′-bis(tert-butoxycarbonyl)carbamimidoyl]amino]pentyl]carbamate



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Tert-butyl ((4-(4-hydroxybutoxy)phenyl)(imino)methyl)carbamate (0.25 g) was dissolved in tetrahydrofuran (10 mL). Tert-butyl N—[N,N′-bis(tert-butoxycarbonyl) carbamimidoyl]-N-[5-[[N,N′-bis(tert-butoxycarbonyl)carbamimidoyl]amino]pentyl]carbamate (0.58 g) was added to the solution at room temperature. Triphenylphosphine (0.36 g) and bis(2-methoxyethyl)azodicarboxylate (0.35 g) were added to the mixture at room temperature. The resultant was stirred overnight and then concentrated, followed by purifying the resulting residue by silica gel column chromatography to obtain the title compound (0.33 g).



1HNMR (CDCl3): 1.21-1.70 (m, 60H), 1.75-1.89 (m, 4H), 3.34 (q, 2H), 3.50 (t, 2H), 3.57 (t, 2H), 4.01 (t, 2H), 6.89 (d, 2H), 7.85 (d, 2H).


EXAMPLE 59
Synthesis of hydrochloride salt of 4-[3-[[(5-guanidinopentyl)carbamimidoyl]amino]butoxy]benzamidine



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The title compound (compound No. 59) was obtained in the same manner as in Example 2.



1H NMR (CD3OD): 1.41-1.53 (m, 2H), 1.58-1.71 (m, 4H), 1.75-1.97 (m, 4H), 3.16-3.25 (m, 4H), 3.26-3.37 (m, 2H), 4.15 (t, 2H), 7.14 (d, 2H), 7.79 (d, 2H).


EXAMPLE 60
(Step 1) Synthesis of tert-butyl N-[N,N′-bis(tert-butoxycarbonyl)carbamimidoyl]-N-[4-[[5-(N-tert-butoxycarbonylcarbamimidoyl)-2-pyridyl]oxy]butyl]carbamate



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Tert-butyl N-[6-(4-bromobutoxy)pyridine-3-carboximidoyl]carbamate (0.50 g) and 1,2,3-tris(tert-butoxycarbonyl)guanidine (0.97 g) were dissolved in N, N-dimethylformamide (13 mL). Potassium carbonate (0.20 g) was added to the solution, and the resultant was stirred at room temperature overnight. Then, the reaction mixture was cooled to room temperature, water was added thereto, and then the resultant was subjected to extraction with chloroform. The resultant organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography to obtain the title compound (0.16 g, in a yield of 18%).



1H NMR (CDCl3): 1.45-1.57 (m, 36H), 1.73-1.88 (m, 4H), 3.79-3.93 (m, 2H), 4.29-4.40 (m, 2H), 6.71 (d, 1H), 8.12 (dd, 1H), 8.59 (d, 1H).


(Step 2) Synthesis of tert-butyl N—[N,N′-bis(tert-butoxycarbonyl)-N-[4-[[5-(N-tert-butoxy carbonylcarbamimidoyl)-2-pyridyl]oxy]butyl]carbamimidoyl]-N-[8-[[N,N′-bis(tert-butoxy carbonyl)carbamimidoyl]amino]octyl]carbamate



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The tert-butyl N-[N,N′-bis(tert-butoxycarbonyl)carbamimidoyl]-N-[4-[[5-(N-tert-butoxycarbonylcarbamimidoyl)-2-pyridyl]oxy]butyl]carbamate (0.16 g) obtained in the step 1 and tert-butyl N-[(8-bromooctylamino)-(tert-butoxycarbonylamino)methylene]carbamate (0.17 g) were dissolved in N, N-dimethylformamide (5 mL). Potassium carbonate (0.07 g) was added to the solution and the mixture was stirred at 50° C. overnight. Then, the reaction mixture was cooled to room temperature, water was added thereto, and the resultant was subjected to extraction with chloroform. The resultant organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography to obtain the title compound (compound No. 60: 81 mg, in a yield of 32%).



1H NMR (CDCl3): 1.08-1.37 (m, 10H), 1.39-1.65 (m, 56H), 1.73-1.88 (m, 4H), 3.48 (t, 2H), 3.60 (t, 2H), 3.82 (t, 2H), 4.34 (t, 2H), 6.71 (d, 1H), 8.20 (dd, 1H), 8.69 (d, 1H).


EXAMPLE 61
Synthesis of hydrochloride salt of 6-[4-[[N-(8-guanidinooctyl)carbamimidoyl]amino]butoxy]pyridine-3-carboxamidine



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The title compound (compound No. 61) was obtained in the same manner as in Example 2.



1H NMR (CD3OD): 1.32-1.66 (m, 12H), 1.70-1.90 (m, 4H), 3.13-3.23 (m, 4H), 3.28 (t, 2H), 4.39-4.53 (m, 2H), 6.95-7.04 (m, 1H), 8.04-8.17 (m, 1H), 8.61-8.70 (m, 1H).


EXAMPLE 62
Synthesis of tert-butyl N-[N-tert-butoxycarbonyl-N-[3-[4-(N-tert-butoxycarbonyl carbamimidoyl)phenoxy]propyl]-N′-phenyl-carbamimidoyl]-N-[3-[4-(N-tert-butoxy carbonylcarbamimidoyl)phenoxy]propyl]carbamate



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Tert-butyl N-[4-(3-bromopropoxy)benzenecarboximidoyl]carbamate (0.27 g) and tert-butyl N-(N-tert-butoxycarbonyl-N′-phenyl-carbamimidoyl)carbamate (0.60 g) were dissolved in N, N-dimethylformamide (5 mL). Potassium carbonate (0.56 g) was added to the solution, and then the mixture was stirred at 50° C. overnight. Then, the reaction mixture was cooled to room temperature, water was added thereto, and the resultant was subjected to extraction with chloroform. The resultant organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography to obtain the title compound (compound No. 62: 0.30 g, in a yield of 42%).



1H NMR (CDCl3): 1.35-1.60 (m, 38H), 2.24 (tt, 2H), 3.25 (t, 2H), 3.71 (t, 2H), 3.99 (t, 2H), 4.11 (t, 2H), 6.74 (d, 2H), 6.80 (d, 2H), 6.86 (d, 2H), 7.02 (dd, 2H), 7.25 (dd, 2H), 7.77 (d, 2H).


EXAMPLE 63
Synthesis of hydrochloride salt of 4-[3-[[N-[3-(4-carbamimidoylphenoxy)propyl]-N′-phenyl-carbamimidoyl]amino]propoxy]benzamidine



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The title compound (compound No. 63) was obtained in the same manner as in Example 2.



1HNMR (CD3OD): 2.02-2.26 (m, 4H), 3.50-3.62 (m, 4H), 4.20 (t, 2H), 7.11 (d, 2H), 7.23 (d, 2H), 7.33 (t, 1H), 7.43 (dd, 2H), 7.79 (d, 2H).


EXAMPLE 64
Synthesis of tert-Butyl N-[N,N′-bis(tert-butoxycarbonyl)-N-[3-[4-(N-tert-butoxycarbonyl carbamimidoyl)phenyl]propyl]carbamimidoyl]-N-[3-[4-(N-tert-butoxycarbonyl carbamimidoyl)phenyl]propyl]carbamate



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Tert-butyl N-[N, N′-bis(tert-butoxycarbonyl)-N-[3-[4-(N-tert-butoxycarbonyl carbamimidoyl)phenyl]prop-2-ynyl]carbamimidoyl]-N-[3-[4-(N-tert-butoxycarbonyl carbamimidoyl)phenyl]prop-2-ynyl]carbamate (450 mg) was dissolved in methanol (5 mL), and palladium on carbon (45 mg) was added thereto at room temperature. The mixture was stirred under a hydrogen atmosphere at the same temperature overnight. The reaction mixture was filtered and concentrated under reduced pressure to obtain the title compound (compound No. 64: 90.8 mg, in a yield of 20%).



1H NMR (CDCl3): 1.43-1.56 (m, 45H), 1.87-1.98 (m, 4H), 2.62 (t, 4H), 3.52 (dd, 4H), 7.17 (d, 2H), 7.71 (d, 2H).


EXAMPLE 65
Synthesis of hydrochloride salt of 4-[3-[[N-[3-(4-carbamimidoylphenyl)propyl]carbamimidoyl]amino]propyl]benzamidine



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The title compound (compound No. 65) was obtained in the same manner as in Example 2.



1HNMR (CD3OD): 1.95 (dt, 4H), 2.83 (dd, 4H), 3.27 (dd, 4H), 7.51 (d, 4H), 7.75 (d, 4H)


EXAMPLE 66
Synthesis of di-tert-butyl [[[[2-[[2,2,2-trifluoroacetyl]imino]-1H-imidazole-1,3 [2H]-diyl]bis[propane-3,1-diylsulfonyl]]bis[4,1-phenylene]]bis[iminomethylene]]dicarbamate



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Di-tert-butyl [[[[[2-[[2,2,2-trifluoroacetyl]imino]-1H-imidazole-1,3[2H]-diyl]bis[propane-3,1-diyl]]bis[sulfanediyl]]bis[4,1-phenylene]]bis[iminomethylene]]dicarbamate (168 mg) was dissolved in dichloromethane (5 mL). 3-chloroperbenzoic acid (268 mg) was added to the solution at room temperature. The mixture was stirred for 1.5 hours, and the resultant was poured into water to conduct extraction with ethyl acetate. The resultant organic layer was washed sequentially with saturated aqueous sodium thiosulfate solution, saturated aqueous sodium hydrogen carbonate solution, and saturated saline solution, and then dried over anhydrous sodium sulfate, followed by filtering. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain the title compound (compound No. 66: 116 mg).



1H NMR (CDCl3): 1.56 (s, 18H), 2.22 (tt, 4H), 3.12 (t, 4H), 4.03 (t, 4H), 6.86 (s, 2H), 7.85 (d, 4H), 7.91 (d, 4H).


EXAMPLE 67
Synthesis of hydrochloride salt of 4-[3-[3-[3-(4-carbamimidoylphenyl)sulfonylpropyl]-2-imino-imidazol-1-yl]propylsulfonyl]benzamidine



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The title compound (compound No. 67) was obtained in the same manner as in Example 52.



1HNMR (CD3OD): 2.11-2.26 (m, 4H), 3.42 (t, 4H), 4.05 (t, 4H), 6.99 (s, 2H), 8.05 (d, 4H), 8.18 (d, 4H).


EXAMPLE 68
Synthesis of tert-butyl N-[N-tert-butoxycarbonyl-N-[4-[4-(N-tert-butoxycarbonyl carbamimidoyl)phenoxy]butyl]-N′-phenyl-carbamimidoyl]-N-[4-[4-(N-tert-butoxycarbonylcarbamimidoyl)phenoxy]butyl]carbamate (compound No. 68-1) and tert-butyl N-[N′-tert-butoxycarbonyl-N-[4-[4-(N-tert-butoxycarbonylcarbamimidoyl)phenoxy]butyl]-N-phenyl-carbamimidoyl]-N-[4-[4-(N-tert-butoxycarbonylcarbamimidoyl)phenoxy]butyl]carbamate (compound No. 68-2)



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Tert-butyl N-[4-(4-bromobutoxy)benzenecarboximidoyl]carbamate (3.03 g) and tert-butyl N-(N-tert-butoxycarbonyl-N′-phenyl-carbamimidoyl)carbamate (1.25 g) were dissolved in N, N-dimethylformamide (5 mL), potassium carbonate (2.06 g) was added thereto, and the mixture was stirred at 60° C. overnight. Then, the reaction mixture was cooled to room temperature, water was added thereto, and the resultant was subjected to extraction with ethyl acetate. The resultant organic layer was dried over anhydrous magnesium sulfate, filtered, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound (compound No. 68-1: 590 mg, in a yield of 17%) and the title compound (compound No. 68-2: 152 mg, in a yield of 4.5%).

  • Compound No. 68-1:



1H NMR (CDCl3): 1.37 (s, 9H), 1.43-1.68 (m, 31H), 1.75-1.98 (m, 4H), 3.16 (t, 2H), 3.79 (t, 2H), 3.85 (t, 2H), 3.99 (t, 2H), 6.75-6.88 (m, 6H), 7.03 (dd, 2H), 7.26 (d, 2H), 7.72-7.82 (m, 4H).

  • Compound No. 68-2:



1H NMR (CDCl3): 1.41-1.72 (m, 40H), 1.73-1.91 (m, 4H), 2.89-3.15 (m, 2H), 3.71-4.08 (m, 6H), 6.80 (d, 2H), 6.82 (d, 2H), 7.20-7.36 (m, 5H), 7.73-7.84 (m, 4H).


EXAMPLE 69
Synthesis of hydrochloride salt of 4-[4-[[N-[4-(4-carbamimidoylphenoxy)butyl]-N′-phenyl-carbamimidoyl]amino]butoxy]benzamidine



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The title compound (compound No. 69) was obtained in the same manner as in Example 2.



1HNMR (CD3OD): 1.77-1.97 (m, 8H), 3.36-3.47 (m, 4H), 4.14 (t, 4H), 7.12 (d, 4H), 7.28 (d, 2H), 7.34 (dd, 1H), 7.47 (dd, 2H), 7.79 (d, 4H).


EXAMPLE 70
Synthesis of hydrochloride salt of 4-[4-[[N-[4-(4-carbamimidoylphenoxy)butyl]-N-phenyl-carbamimidoyl]amino]butoxy]benzamidine



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The title compound (compound No. 70) was obtained in the same manner as in Example 2.



1HNMR (CD3OD): 1.71-1.93 (m, 8H), 3.63-3.69 (m, 2H), 3.80 (t, 2H), 4.08 (t, 2H), 4.12 (t, 2H), 7.07 (d, 2H), 7.12 (d, 2H), 7.37 (d, 2H), 7.49 (dd, 1H), 7.56 (dd, 2H), 7.72-7.84 (m, 4H).


EXAMPLE 71
(Step 1) Synthesis of 2,2,2-trifluoro-N-[3-[8-[2-(2,2,2-trifluoroacetyl)imino-1H-imidazol-3-yl]octyl]-1H-imidazol-2-ylidene]acetamide



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N-(1,3-dihydroimidazol-2-ylidene)-2,2,2-trifluoro-acetamide (5 g) was dissolved in acetonitrile (50 mL) and benzene (15 mL). Potassium carbonate (3.86 g) and dibromooctane (2.53 g) were added to the solution at room temperature. The reaction mixture was heated to 60° C., and stirred at the same temperature overnight. The reaction mixture was cooled to room temperature, water was added thereto, and the resultant was subjected to extraction with ethyl acetate. The resultant organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound (3.27 g, in a yield of 75.0%).



1NMR (CDCl3): 1.24-1.37 (m, 8H), 1.76 (tt, 4H), 3.99 (dd, 4H), 6.65 (d, 2H), 6.81 (d, 2H).


(Step 2) Synthesis of tert-butyl 2-[4-[3-[2-(2,2,2-trifluoroacetyl)imino-3-[8-[2-(2,2,2-trifluoroacetyl)imino-1H-imidazol-3-yl]octyl]imidazol-1-yl]propoxy]phenyl]-5,6-dihydro-4H-pyrimidine-1-carboxylate



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2,2,2-trifluoro-N-[3-[8-[2-(2,2,2-trifluoroacetypimino-1H-imidazol-3-yl]octyl]-1H- imidazol-2-ylidene]acetamide (943 mg) obtained in the step 1 was dissolved in acetonitrile (10 mL) and benzene (3 mL). Potassium carbonate (417 mg) and tert-butyl 2-[4(3bromopropoxy)phenyl]-5,6-dihydro-4H-pyrimidine-1 -carboxylate (800 mg) were added to the solution at room temperature. The reaction mixture was heated to 50° C. and stirred at the same temperature overnight. The reaction mixture was cooled to room temperature, water was added thereto, and the resultant was subjected to extraction with ethyl acetate. The resultant organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound (compound No. 282: 337 mg, in a yield of 21.0%).



1H NMR (CDCl3): 1.16 (s, 9H), 1.24-1.36 (m, 8H), 1.69-1.79 (m, 4H), 1.92 (dt, 2H), 2.24 (tt, 2H), 3.60 (dd, 2H), 3.70 (dd, 2H), 3.83 (dd, 2H), 3.95 (dd, 2H), 3.98 (dd, 2H), 4.12 (dd, 2H), 6.67-6.71 (m, 3H), 6.80 (d, 1H), 6.83 (d, 2H), 7.42 (d, 2H).


EXAMPLE 72
Synthesis of tert-butyl 2-[42-[3-[[N,N ′-bis(tert-butoxycarbonyl)carbamimidoyl]amino]octyl]-2-imino-imidazolidin-1-yl]ethoxy]phenyl]-5,6-dihydro-4H-pyrimidine-1-carboxlate



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Tert-butyl 2-[4-[2-(2-iminoimidazolidin-1-yl)ethoxy]phenyl]-5,6-dihydro-4H- pyrimidine-1-carboxylate (140 mg) was dissolved in N, N-dimethylformamide (5 mL). Potassium carbonate (153 mg) and tert-butyl N-[(8-bromooctylamino)-(tert-butoxy carbonylamino)methylene]carbamate (333 mg) were added to the solution at room temperature.


The reaction mixture was stirred at the same temperature overnight. Water was added to the reaction mixture, and the mixture was subjected to extraction with ethyl acetate. The resultant organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound (compound No. 315: 119 mg, in a yield of 42.5%).



1H NMR (CDCl3): 1.16 (s, 9H), 1.24-1.36 (m, 8H), 1.47-1.54 (m, 20H), 1.59-1.72 (m, 2H), 1.94 (tt, 2H), 3.02-3.17 (m, 2H), 3.24 (dd, 2H), 3.42 (dd, 2H), 3.56-3.65 (m, 4H), 3.69 (dd, 2H), 3.88 (dd, 2H), 4.16 (dd, 2H), 6.89 (d, 2H), 7.41 (d, 2H)


The following compounds were synthesized taking into account Examples 1 to 72 and Synthesis Examples 1 to 9.










TABLE 74







Compound



No.
Structure





71


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72


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73


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74


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75


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76


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77


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78


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79


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80


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Compound





No.
Salt form
Physical property






71


1HNMR (CDCl3): 1.44-1.60 (m, 36H), 2.02-2.19






(m, 4H), 3.00 (s, 3H), 3.24-3.49 (m, 2H), 3.51-3.69





(m, 2H), 3.83-4.04 (m, 4H), 6.69-6.93 (m, 4H),





7.64-7.84 (m, 4H)



72
hydro-

1HNMR (CD3OD): 2.13 (dt, 4H), 3.08 (s, 3H),





chloride
3.43-3.49 (m, 2H), 3.62 (dd, 2H), 4.15-4.21 (m,





4H), 7.16 (dd, 4H), 7.80 (dd, 4H)



73


1HNMR (CDCl3): 1.55 (s, 18H), 4.27 (dd, 4H),






4.33 (dd, 4H), 6.85 (d, 4H), 6.91 (s, 2H), 7.76 (d,





4H)



74
hydro-

1HNMR (CD3OD): 4.34-4.43 (m, 8H), 7.09 (s,





chloride
2H), 7.17 (d, 4H), 7.79 (d, 4H)



75


1HNMR (CDCl3): 1.16 (s, 18H), 1.92 (dt, 4H),






2.29 (dt, 4H), 3.60 (dd, 4H), 3.70 (dd, 4H), 3.99 (t,





4H), 4.22 (t, 4H), 6.74 (s, 2H), 6.84 (d, 4H), 7.43





(d, 4H)



76
hydro-

1HNMR (CD3OD): 2.10 (dt, 4H), 2.26 (dt, 4H),





chloride
3.57 (dd, 8H), 4.11 (dd, 4H), 4.15 (dd, 4H), 6.97 (s,





2H), 7.13 (d, 4H), 7.67 (d, 4H)



77


1HNMR (CDCl3): 1.31 (s, 18H), 1.46-1.53 (m,






27H), 2.16 (dd, 4H), 3.73 (dd, 4H), 3.90 (dd, 4H),





3.95 (dd, 4H), 4.02 (t, 4H), 6.85 (d, 4H), 7.45 (d,





4H)



78
hydro-

1HNMR (CD3OD): 2.11 (dd, 4H), 2.55-2.92 (m,





chloride
4H), 3.35-3.49 (m, 8H), 4.20 (t, 4H), 7.18 (d, 4H),





7.84 (d, 4H)



79


1HNMR (CDCl3): 1.44 (s, 18H), 1.50 (s, 9H),






1.57 (s, 18H), 2.09 (tt, 4H), 2.78 (t, 4H), 3.62 (t,





4H), 6.36 (s, 2H), 7.29 (d, 2H), 7.64 (dd, 2H), 7.97





(d, 2H).



80
hydro-
Melting point 174-182° C.




chloride









In the table, Boc or BOC indicates a t-butoxycarbonyl group. In the table, “-” means that a compound was synthesized as free form.










TABLE 75







Compound



No.
Structure





81


embedded image







82


embedded image







83


embedded image







84


embedded image







85


embedded image







86


embedded image







87


embedded image







88


embedded image







89


embedded image







90


embedded image
















Compound





No.
Salt form
Physical property






81


1HNMR (CDCl3): 1.44 (s, 18H), 1.50 (s, 9H),






1.57 (s, 18H), 2.09 (tt, 4H), 2.78 (t, 4H), 3.62 (t,





4H), 6.36 (s, 2H), 7.29 (d, 2H), 7.64 (dd, 2H), 7.97





(d, 2H).



82
hydro-
Melting point 181-185° C.




chloride




83


1HNMR (CDCl3): 1.46 (s, 18H), 1.49 (s, 9H),






1.56 (s, 18H), 1.77-1.90 (m, 8H), 3.62 (t, 4H), 3.94





(t, 4H), 6.67 (d, 2H), 7.59 (dd, 2H), 7.66 (d, 2H).



84
hydro-
Melting point 171-180° C.




chloride




85


1HNMR (CDCl3): 1.47 (s, 18H), 1.50 (s, 9H),






1.56 (s, 18H), 1.79-1.95 (m, 8H), 3.66 (t, 4H), 3.96





(t, 4H), 6.62 (d, 2H), 7.53 (dd, 2H), 7.86 (d, 2H).



86
hydro-

1HNMR (CD3OD): 1.80-2.01 (m, 8H), 3.33 (m,





chloride
4H), 4.24 (t, 4H), 7.31 (d, 2H), 7.78 (dd, 2H), 7.91





(d, 2H).



87


1HNMR (CDCl3): 1.46-1.56 (m, 22H), 1.76-1.87






(m, 8H), 3.90 (t, 4H), 3.97 (t, 4H), 6.73 (s, 2H),





6.87 (d, 4H), 7.80 (d, 4H)



88
hydro-

1HNMR (CD3OD): 1.52-1.61 (m, 4H), 1.79-1.93





chloride
(m, 8H), 3.90 (t, 4H), 4.11 (t, 4H), 6.99 (s, 2H),





7.12 (d, 4H), 7.77 (d, 4H)



89
acetate
Melting point 190-195° C.



90


1HNMR (CDCl3): 1.33-1.41 (m, 2H), 1.44-158






(m, 45H), 1.71 (dt, 2H),1.79 (dt, 2H), 2.16 (dd, 2H),





2.96 (dd, 2H), 3.49 (dd, 2H), 3.72 (dd, 2H), 4.06 (t,





2H), 6.88 (d, 2H), 7.80 (dt 2H), 8.21 (s, 1 H)









In the table, Boc or BOC indicates a t-butoxycarbonyl group. In the table, “-” means that a compound was synthesized as free form.










TABLE 76







Compound



No.
Structure





91


embedded image







92


embedded image







93


embedded image







94


embedded image







95


embedded image







96


embedded image







97


embedded image







98


embedded image







99


embedded image







100


embedded image
















Compound





No.
Salt form
Physical property






91
hydro-

1HNMR (CD3OD): 1.50 (dt, 2H), 1.66 (dt, 2H),





chloride
1.88 (dt, 2H), 2.11 (dt, 2H), 3.11 (t, 2H), 3.17-3.24





(m, 2H), 3.40-3.47 (m, 2H), 4.18 (t, 2H), 7.12 (d,





2H), 7.80 (d, 2H), 8.56 (s, 1 H)



92


1HNMR (CDCl3): 1.52-1.58 (m, 20H), 1.74-1.86






(m, 4H), 3.88-3.98 (m, 4H), 4.24-4.37 (m, 4H),





6.73 (d, 1H), 6.82 (d, 2H), 6.87 (d, 2H), 6.98 (d,





1H), 7.75-7.83 (m, 4H)



93
hydro-
Melting point 183-187° C.




chloride




94


1HNMR (CDCl3): 1.41 (dt, 4H), 1.55 (s, 18H),






1.82 (dt, 8H), 2.99 (t, 4H), 3.87 (t, 4H), 6.70 (s,





2H), 8.20 (s, 2H)



95
hydro-

1HNMR (CD3OD): 1.48 (dt, 4H), 1.81 (dt, 4H),





chloride
1.91 (dt, 4H), 3.12 (t, 4H), 3.88 (t, 4H), 6.97 (s,





2H), 8.57 (s, 2H)



96


1HNMR (CDCl3): 1.34-1.48 (m, 36H), 2.24 (dt,






4H), 2.90 (s, 6H), 3.42-3.58 (m, 8H), 3.96 (1, 4H),





4.11 (t, 4H), 6.70 (s, 2H), 6.80-6.89 (m, 4H), 7.40





(d, 4H)



97
hydro-

1HNMR (CD3OD): 2.25 (dt, 4H), 2.91 (s, 6H),





chloride
3.46-3.54 (m, 8H), 3.92 (dd, 4H), 4.08 (dd, 4H),





6.95 (s, 2H), 6.84-6.92 (m, 4H), 7.82 (d, 4H)



98


1HNMR (CD3OD): 1.51 (s, 18H), 2.29 (tt, 4H),






4.08-4.17 (m, 8H), 7.07 (d, 2H), 7.20 (s, 2H), 7.75





(dd, 2H), 7.90 (d, 2H).



99
hydro-
Melting point 184-190° C.




chloride




100


1HNMR (CDCl3): 1.35-1.47 (m, 18H), 1.55 (s,






9H), 2.24 (dd, 4H), 2.90 (s, 3H), 3.44-3.58 (m, 4H),





3.91-3.99 (m, 4H), 4.08-4.17 (m, 4H), 6.69 (s, 2H),





6.78-6.87 (m, 4H), 7.38 (d, 2H), 7.82 (d, 2H)









In the table, Boc or BOC indicates a t-butoxycarbonyl group. In the table, “-” means that a compound was synthesized as free form.










TABLE 77







Compound



No.
Structure





101


embedded image







102


embedded image







103


embedded image







104


embedded image







105


embedded image







106


embedded image







107


embedded image







108


embedded image







109


embedded image







110


embedded image
















Compound





No.
Salt form
Physical property






101
hydro-

1HNMR (CD3OD): 2.27 (dt, 4H), 2.81 (s, 3H),





chloride
3.43 (t, 2H), 3.85 (t, 2H), 4.06-4.20 (m, 8H), 6.98





(s, 2H), 7.15 (d, 4H), 7.80 (d, 2H), 7.86 (d, 2H)



102


1HNMR (CD3OD): 1.50 (s, 18H), 2.23 (tt, 4H),






4.02 (t, 4H), 4.10 (t, 4H), 6.71-6.81 (m, 4H), 7.21





(s, 2H), 7.63 (t, 2H).



103
hydro-
Melting point183-187° C.




chloride




104


1HNMR (CD3OD): 1.51 (s, 18H), 1.74-1.92 (m,






8H), 2.20 (s, 6H), 3.92 (t, 4H), 4.03 (t, 4H), 6.96 (d,





4H), 7.78 (d, 4H).



105
hydro-

1HNMR (CD3OD): 1.89 (s, 8H), 2.16 (s, 6H),





chloride
3.94 (t, 4H), 4.15 (t, 4H), 7.13 (d, 4H), 7.79 (d, 4H).



106


1HNMR (CD3OD): 1.81-1.99 (m, 8H), 2.21 (d,






3H), 3.88-3.99 (m, 4H), 4.11-4.18 (m, 4H), 6.75 (d,





1H), 7.13 (dd, 4H), 7.79 (dd, 4H).



107
hydro-

1HNMR (CD3OD): 1.51 (s, 18H), 1.72-1.99 (m,





chloride
8H), 2.25 (d, 3H), 3.90 (t, 2H), 3.95 (t, 2H), 4.04 (q,





4H), 6.94-6.99 (m, 5H), 7.78 (d, 4H).



108


1HNMR (CDCl3): 1.55 (s, 18H), 2.12 (d, 3H),






2.17-2.25 (m, 4H), 3.95 (q, 4H), 4.01-4.10 (m, 4H),





6.43 (d, 1H), 6.85 (dd, 4H), 7.81 (d, 4H).



109
hydro-
Melting point 188-199° C.




chloride




110
albesi-
Melting point 218-224° C.




late









In the table, Boc or BOC indicates a t-butoxycarbonyl group. In the table, “-” means that a compound was synthesized as free form.










TABLE 78







Compound



No.
Structure





111


embedded image







112


embedded image







113


embedded image







114


embedded image







115


embedded image







116


embedded image







117


embedded image







118


embedded image







119


embedded image







120


embedded image
















Compound





No.
Salt form
Physical property






111


1HNMR (CDCl3): 1.14-1.27 (m, 8H), 1.44-1.59






(m, 58H), 2.22 (dt, 2H), 3.33 (dd, 2H), 3.48 (dd,





2H), 3.76 (dd, 2H), 4.15 (dd, 2H), 6.95 (d, 1H), 7.82





(dd, 1H), 8.03 (dd, 1H)



112
hydro-

1HNMR (CD3OD): 1.35-1.44 (m, 8H), 1.55-1.64





chloride
(m, 4H), 2.17 (dd, 2H), 3.11-3.23 (m, 4H), 3.43-





3.51 (m, 2H), 4.29 (t, 2H), 7.33 (d, 1H), 7.78 (dd,





1H), 7.92 (d, 1H)



113


1HNMR (CDCl3): 1.55 (s, 18H), 2.12 (d, 3H),






2.17-2.25 (m, 4H), 3.95 (q, 4H), 4.01-4.10 (m, 4H),





6.43 (d, 1H), 6.85 (dd, 4H), 7.81 (d, 4H).



114
hydro-
Melting point 182-186° C.




chloride




115


1HNMR (CDCl3): 1.19 (s, 18H), 2.25 (dt, 4H),






3.33 (s, 6H), 3.97 (t, 4H), 4.12 (t, 4H), 6.72 (s, 2H),





6.84 (d, 4H), 7.37 (d, 4H)



116
hydro-

1HNMR (CD3OD): 2.26 (dt, 4H), 3.08 (s, 6H),





chloride
4.11 (t, 4H), 4.16 (t, 4H), 6.98 (s, 2H), 7.13 (d, 4H),





7.72 (d, 4H)



117


1HNMR (CDCl3): 1.18 (s, 18H), 1.76-1.86 (m,






4H), 1.98 (dt, 4H), 3.33 (s, 6H), 3.97 (t, 4H), 4.00





(t, 4H), 6.80 (s, 2H), 6.86 (d, 4H), 7.36 (d, 4H)



118
hydro-

1HNMR (CD3OD): 1.83-2.02 (m, 8H), 3.08 (s,





chloride
6H), 3.97 (t, 4H), 4.14 (t, 4H), 7.00 (s, 2H), 7.10 (d,





4H), 7.70 (d, 4H)



119


1HNMR (CDCl3): 1.20-1.31 (m, 8H), 1.46-1.68






(m, 58H), 2.11-2.20 (m, 2H), 3.33 (dd, 2H), 3.49





(dd, 2H), 3.70 (dd, 2H), 4.38 (dd, 2H), 6.74 (d, 1H),





8.14 (dd, 1H), 8.32 (dd, 1H)



120
hydro-

1HNMR (CD3OD): 1.34-1.44 (m, 8H), 1.54-1.65





chloride
(m, 4H), 2.10 (dt, 2H), 3.17 (dd, 4H), 3.40 (t, 2H),





4.50 (t, 2H), 7.00 (d, 1H), 8.07 (dd, 1H), 8.65 (d,





1H)









In the table, Boc or BOC indicates a t-butoxycarbonyl group. In the table, “-” means that a compound was synthesized as free form.










TABLE 79







Compound



No.
Structure





121


embedded image







122


embedded image







123


embedded image







124


embedded image







125


embedded image







126


embedded image







127


embedded image







128


embedded image







129


embedded image







130


embedded image
















Compound





No.
Salt form
Physical property






121


1HNMR (CDCl3): 1.19 (s, 9H), 1.55 (s, 9H),






2.19-2.28 (m, 4H), 3.33 (s, 3H), 3.97 (dd, 4H), 4.12





(t, 4H), 6.70 (dd, 2H), 6.82-6.91 (m, 4H), 7.37 (d,





2H), 7.82 (d, 2H)



122
hydro-

1HNMR (CD3OD): 2.23-2.32 (m, 4H), 3.08 (s,





chloride
3H), 4.08-4.20 (m, 8H), 6.98 (s, 2H), 7.11-7.18 (m,





4H), 7.72 (d, 2H), 7.80 (d, 2H)



123


1HNMR (CDCl3): 1.18 (s, 9H), 1.55 (s, 9H),






1.80-1.85 (m, 2H), 1.97 (dt, 2H), 2.25 (dt, 2H),





3.33 (s, 3H), 3.93-4.02 (m, 6H), 4.12 (t, 2H), 6.75





(d, 2H), 6.85 (d, 2H), 6.89 (d, 2H), 7.36 (d, 2H),





7.81 (d, 2H)



124
hydro-

1HNMR (CDOD): 1.84-2.00 (m, 4H), 2.28 (dt,





chloride
2H), 3.07 (s, 3H), 3.96 (t, 2H), 4.12 (t, 4H), 4.17 (t,





2H), 7.00 (d, 2H), 7.11 (d, 2H), 7.15 (d, 2H), 7.70





(d, 2H), 7.80 (d, 2H)



125


1HNMR (CDCl3): 1.55 (s, 9H), 1.56 (s, 9H),






2.17-2.27 (m, 4H), 2.81 (t, 2H), 3.93-3.99 (m, 4H),





4.10 (t, 2H), 6.45 (s, 1H), 6.70 (dd, 2H), 6.86 (d,





2H), 7.40 (d, 1H), 7.73 (dd, 1H), 7.81 (d, 2H), 8.02





(d, 1H).



126
hydro-
Melting point 227-236° C.




chloride




127


1HNMR (CDCl3): 1.19-1.32 (m, 8H), 1.42-1.54






(m, 47H), 1.57-1.64 (m, 2H), 2.02 (dt, 2H), 3.01





(s, 3H), 3.42 (dd, 2H), 3.50 (dd, 2H), 3.63 (t, 2H),





4.11 (t, 2H), 6.86 (d, 2H), 7.42 (d, 2H)



128
hydro-

1HNMR (CD3OD): 1.18-1.33 (m, 8H), 1.36-1.47





chloride
(m, 2H), 1.55-1.62 (m, 2H), 2.00-2.06 (m, 2H),





3.02 (s, 3H), 3.39 (dd, 2H), 3.44-3.52 (m, 2H), 3.61





(t, 2H), 4.02 (t, 2H), 6.82 (d, 2H), 7.39 (d, 2H)



129


1HNMR (CDCl3): 1.55 (s, 18H), 2.03-2.09 (m,






4H), 2.83 (s, 6H), 3.34 (t, 4H), 4.00 (t, 4H), 5.77 (d,





4H), 7.73 (d, 4H)



1.30
hydro-

1HNMR (CD3OD): 2.01-2.12 (m, 4H), 2.81 (s,





chloride
6H), 3.30 (t, 4H), 4.05 (t, 4H), 6.80 (d, 4H), 7.75 (d,





4H)









In the table, Boc or BOC indicates a t-butoxycarbonyl group. In the table, “-” means that a compound was synthesized as free form.










TABLE 80







Compound



No.
Structure





131


embedded image







132


embedded image







133


embedded image







134


embedded image







135


embedded image







136


embedded image







137


embedded image







138


embedded image







139


embedded image







140


embedded image
















Compound





No.
Salt form
Physical property






131


1HNMR (CDCl3): 1.40-1.61 (m, 60H), 2.15 (tt,






2H), 3.27 (q, 2H), 3.44 (dd, 2H), 3.71 (t, 2H), 4.10





(t, 2H), 6.90 (d, 2H), 7.90 (d, 2H).



132
hydro-

1HNMR (CD3OD): 1.41-1.50 (m, 2H), 1.58-1.68





chloride
(m, 4H), 2.12 (tt, 2H), 3.16-3.25 (m, 4H), 3.44 (t,





2H), 4.20 (t, 2H), 7.17 (d, 2H), 7.81 (d, 2H).



133


1HNMR (CDCl3): 1.19-1.27 (m, 4H), 1.40-1.63






(m, 58H), 2.16 (tt, 2H), 3.31 (q, 2H), 3.45 (dd, 2H),





3.73 (t, 2H), 4.08 (t, 2H), 6.90 (d, 2H), 7.88 (d, 2H).



134
hydro-

1HNMR (CD3OD): 1.35-1.48 (m, 4H), 1.54-1.68





chloride
(m, 4H), 2.12 (tt, 2H), 3.19 (q, 4H), 3.44 (t, 2H),





4.20 (t, 2H), 7.17 (d, 2H), 7.81 (d, 2H).



135


1HNMR (CDCl3): 1.24-1.68 (m, 62H), 1.75-1.91






(m, 4H), 3.32 (q, 2H), 3.44-3.52 (m, 2H), 3.59 (t,





2H), 4.00 (t, 2H), 6.88 (d, 2H), 7.85 (d, 2H).



136
hydro-

1HNMR (CD3OD): 1.39-1.50 (m, 4H), 1.56-1.67





chloride
(m, 4H), 1.74-1.85 (m, 2H), 1.85-1.95 (m, 2H),





3.20 (q, 4H), 3.29 (t, 2H), 4.14 (t, 2H), 7.13 (d, 2H),





7.79 (d, 2H).



137


1HNMR (CDCl3): 1.55 (s, 9H), 1.96-2.06 (m, 4H),






2.94 (s, 3H), 2.97 (s, 3H), 3.56 (dd, 2H), 3.62 (dd,





2H), 3.95 (dt, 2H), 4.05 (t, 2H), 6.79-6.89 (m, 4H),





7.46 (d, 2H), 7.78 (d, 2H)



138
hydro-

1HNMR (CD3OD): 2.15-2.29 (m, 4H), 2.56 (s,





chloride
3H), 3.08 (s, 3H), 3.89 (dd, 2H), 4.05 (dd, 2H), 4.19





(dd, 4H), 7.11-7.19 (m, 4H), 7.72 (d, 2H), 7.82 (d,





2H)



139


1HNMR (CDCl3): 1.11-1.31 (m, 8H), 1.46-1.59






(m, 51H), 2.04-2.16 (m, 2H), 2.93-3.03 (m, 3H),





3.72-3.89 (m, 4H), 4.01 (t, 2H), 6.88 (d, 2H), 7.84-





7.94 (m, 2H)



140
hydro-

1HNMR (CD3OD): 1.31-1.48 (m, 10H), 1.54-1.69





chloride
(m, 4H), 2.10-2.22 (m, 2H), 3.00-3.09 (m, 3H),





3.14-3.22 (m, 2H), 3.45-3.55 (m, 2H), 4.14-4.27





(m, 2H), 7.13-7.22 (m, 2H), 7.76-7.86 (m, 2H)









In the table, Boc or BOC indicates a t-butoxycarbonyl group. In the table, “-” means that a compound was synthesized as free form.










TABLE 81







Compound



No.
Structure





141


embedded image







142


embedded image







143


embedded image







144


embedded image







145


embedded image







146


embedded image







147


embedded image







148


embedded image







149


embedded image







150


embedded image
















Compound





No.
Salt form
Physical property






141


1HNMR (CDCl3): 1.46 (s, 9H), 1.47 (s, 9H), 1.49






(s, 9H), 1.55 (s, 9H), 1.56 (s, 9H), 1.96 (tt, 2H),





2.13 (tt, 2H), 3.49 (t, 2H), 3.63 (t, 2H), 3.72 (t, 2H),





4.02 (t, 2H), 4.49 (s, 2H), 6.82 (d, 2H), 7.32 (d,





2H), 7.71-7.81 (m, 4H).



142
hydro-

1HNMR (CD3OD): 1.92 (tt, 2H), 2.11 (tt, 2H),





chloride
3.35 (t, 2H), 3.42 (t, 2H), 3.64 (t, 2H), 4.19 (t, 2H),





4.65 (s, 2H), 7.16 (d, 2H), 7.60 (d, 2H), 7.80 (d,





4H).



143
trifluoro-
Melting point 192-197° C.




acetate




144


1HNMR (CDCl3): 1.20-1.35 (m, 8H), 1.43-1.65






(m, 58H), 1.94-2.04 (m, 2H), 3.36 (q, 2H), 3.48 (t,





2H), 3.53 (t, 2H), 3.65 (t, 2H), 4.53 (s, 2H), 7.38 (d,





2H), 7.85 (d, 2H).



145
hydro-

1HNMR (CD3OD): 1.33-1.45 (m, 8H), 1.53-1.63





chloride
(m, 4H), 1.92 (tt, 2H), 3.16 (t, 4H), 3.34 (t, 2H),





3.64 (t, 2H), 4.65 (s, 2H), 7.60 (d, 2H), 7.80 (d,





2H).



146


1HNMR (CDCl3): 1.23-1.33 (m, 10H), 1.43-1.51






(m, 63H), 1.75-1.86 (m, 4H), 2.87 (s, 3H), 3.10-





3.26 (m, 2H), 3.37 (dd, 2H), 3.49 (dd, 2H), 3.59 (dd,





2H), 3.65-3.82 (m, 2H), 4.00 (dd, 2H), 4.12 (dd,





2H), 6.87 (d, 2H), 7.83 (d, 2H)



147
hydro-

1HNMR (CD3OD): 1.36-1.45 (m, 8H), 1.55-1.66





chloride
(m, 4H), 1.70-1.77 (m, 2H), 1.80-1.89 (m, 2H),





3.75 (s, 3H), 3.15-3.26 (m, 8H), 3.60 (dd, 2H), 4.14





(dt, 2H), 7.15 (d, 2H), 7.80 (d, 2H)



148


1HNMR (CDCl3): 1.54 (s, 18H), 2.06 (tt, 2H),






2.29 (tt, 2H), 3.78 (t, 2H), 3.99 (t, 2H), 4.09-4.21





(m, 4H), 6.63 (d, 2H), 6.68 (s, 1H), 6.83 (d, 2H),





7.20 (dd, 2H), 7.33-7.46 (m, 3H), 7.76 (d, 2H), 7.81





(d, 2H).



149
hydro-

1HNMR (CD3OD): 2.06 (tt, 2H), 2.34 (tt, 2H),





chloride
3.93 (t, 2H), 4.15-4.26 (m, 6H), 6.89 (d, 2H), 7.05





(s, 1H), 7.16 (d, 2H), 7.34-7.42 (m, 5H), 7.75 (d,





2H), 7.81 (d, 2H).



150


1HNMR (CDCl3): 1.47 (s, 18H), 1.54-1.57 (m,






27H), 2.55 (dd, 4H), 3.66 (dd, 4H), 6.19 (dt, 2H),





6.35 (d, 2H), 7.23 (d, 2H), 7.71 (d, 2H)









In the table, Boc or BOC indicates a t-butoxycarbonyl group. In the table, “-” means that a compound was synthesized as free form.










TABLE 82







Compound



No.
Structure





151


embedded image







152


embedded image







153


embedded image







154


embedded image







155


embedded image







156


embedded image







157


embedded image







158


embedded image







159


embedded image







160


embedded image
















Compound





No.
Salt form
Physical property






151
hydro-
Melting point 179-181° C.




chloride




152


1HNMR(CDCl3): 1.14-1.23 (m, 8H), 1.46-1.53






(m, 49H), 1.55 (s, 9H), 2.81 (dd, 2H), 3.30 (dd, 2H),





3.48 (dd, 2H), 3.83 (dd, 2H), 7.44 (d, 2H), 7.58 (d,





2H)



153
hydro-

1H NMR (CD3OD): 1.34-1.44 (m, 8H), 1.54-1.65





chloride
(m, 4H), 2.78 (t, 2H), 3.14-3.23 (m, 4H), 3.46-3.53





(m, 2H), 7.64 (d, 2H), 7.77 (d, 2H)



154


1HNMR (CDCl3): 1.48-1.57 (m, 45H), 4.81 (s,






4H), 7.45 (d, 4H), 7.78 (d, 4H)



155
hydro-
Melting point 220° C. UP




chloride




156


1HNMR (CDCl3): 113-1.33 (m, 8H), 1.45-1.57






(m, 58H), 2.60 (dd, 2H), 3.30-3.39 (m, 2H), 3.41-





3.48 (m, 2H), 3.70 (t, 2H), 6.31-6.39 (m, 1H), 6.45





(d, 1H), 7.38 (d, 2H), 7.85 (d, 2H)



157
hydro-

1HNMR (CD3OD): 1.25-1.44 (m, 8H), 1.49-1.65





chloride
(m, 4H), 3.07-3.21 (m, 4H), 3.58-3.74 (m, 4H),





6.45-6.70 (m, 2H), 7.59-7.83 (m, 4H),



158


1HNMR (CDCl3): 1.55 (s, 9H), 1.56 (s, 9H), 2.03






(tt, 2H), 2.23 (tt, 2H), 3.46 (t, 2H), 3.96 (t, 2H),





3.99 (t, 2H), 4.10 (t, 2H), 4.50 (s, 2H), 6.65 (s, 2H),





6.87 (d, 2H), 7.35 (d. 2H), 7.82 (d, 4H).



159
hydro-

1HNMR (CD3OD): 2.07 (tt, 2H), 2.26 (tt, 2H),





chloride
3.60 (t, 2H), 4.03 (t, 2H), 4.10 (t, 2H), 4.16 (t, 2H),





4.62 (s, 2H), 6.96 (q, 2H), 7.14 (d, 2H), 7.60 (d,





2H), 7.81 (dd, 2H).



160


1HNMR (CDCl3): 1.55 (s, 18H), 2.01 (tt, 4H),






3.45 (t, 4H), 3.96 (t, 4H), 4.50 (s, 4H), 6.61 (s, 2H),





7.36 (d, 4H), 7.84 (d, 4H).









In the table, Boc or BOC indicates a t-butoxycarbonyl group. In the table, “-” means that a compound was synthesized as free form.










TABLE 83







Compound



No.
Structure





161


embedded image







162


embedded image







163


embedded image







164


embedded image







165


embedded image







166


embedded image







167


embedded image







168


embedded image







169


embedded image







170


embedded image
















Compound
Salt




No.
form
Physical property






161
hydro-

1HNMR (CD3OD): 2.06 (tt, 4H), 3.59 (t, 4H),





chloride
4.01 (t 4H) 4.63 (s 4H) 6.94 (s 2H) 7.60 (d





4H), 7.81 (d, 4H).



162


1HNMR (CDCl3): 0.82-1.01 (m, 4H), 1.02-1.11






(m, 2H), 1.18-1.32 (m, 20H), 1.44-1.54 (m, 58H),





2.59 (dd, 2H), 3.31-3.39 (m, 2H), 3.73-3.81 (m,





2H), 6.37-6.49 (m, 2H), 7.38 (d, 2H), 7.97 (d, 2H)



163
hydro-

1HNMR (CD3OD): 1.33-1.44 (m, 6H),1.53-1.65





chloride
(m, 4H), 2.55 (dd, 2H), 3.14-3.22 (m, 4H), 3.36-





3.42 (m, 2H), 6.47-6.56 (m, 1H), 6.65 (d, 1H), 7.64





(d, 2H), 7.77 (d, 2H)



164


1HNMR (CDCl3): 1.03-1.21 (m, 6H), 1.35-1.43






(m, 2H), 1.47-1.59 (m, 56H), 1.61-1.69 (m, 2H),





3.22 (dd, 2H), 3.49 (dd, 2H), 4.64 (s, 2H), 7.41 (d,





2H), 7.94 (d, 2H)



165
hydro-

1HNMR(CD3OD): 1.32-1.46 (m, 8H), 1.53-1.67





chloride
(m, 4H), 3.16 (t, 2H), 3.23 (t, 2H), 4.35 (s, 2H),





7.66 (d, 2H), 7.79 (d, 2H)



166


1HNMR(CDCl3): 0.98-1.21 (m, 8H), 1.45-1.59






(m, 58H), 3.29 (dd, 2H), 3.47 (dd, 2H), 4.33 (d, 2H),





6.40 (dt, 1H), 6.58 (d, 1H), 7.40 (d, 2H), 7.91 (d,





2H)



167
hydro-

1HNMR(CD3OD): 1.33-1.46 (m, 8H), 1.54-1.67





chloride
(m, 4H), 3.13-3.19 (m, 2H), 3.22 (t, 2H), 4.08 (d,





2H), 6.50 (dt, 1H), 6.72 (d, 1H), 7.67 (d, 2H), 7.79





(d, 2H)



168


1HNMR(CDCl3): 1.20-1.31 (m, 8H), 1.44-1.62






(m, 58H), 1.91-2.04 (m, 2H), 2.67 (t, 2H), 3.41 (dd,





2H), 3.47 (dd, 2H), 3.54 (dd, 2H), 7.20-7.25 (m,





2H), 7.81 (d, 2H)



169
hydro-

1HNMR(CD3OD): 1.35-1.44 (m, 8H), 1.54-1.67





chloride
(m, 4H), 1.94 (dt, 2H), 2.82 (dd, 2H), 3.14-3.22 (m,





4H), 3.26 (t, 2H), 7.50 (d, 2H), 7.76 (d, 2H)



170


1HNMR(CDCl3): 1 22-1.34 (m, 10H), 1.43-1.54






(m, 58H), 1.68-1.87 (m, 4H), 3.35 (dd, 2H), 3.48





(dt, 2H), 3.53 (dt, 2H), 3.98 (t, 2H), 6.89 (d, 2H),





7.84 (d, 2H)









In the table, Boc or BOC indicates a t-butoxycarbonyl group. In the table, “-” means that a compound was synthesized as free form.










TABLE 84







Compound



No.
Structure





171


embedded image







172


embedded image







173


embedded image







174


embedded image







175


embedded image







176


embedded image







177


embedded image







178


embedded image







179


embedded image







180


embedded image
















Compound
Salt




No.
form
Physical property






171
hydro-

1HNMR (CD3OD): 1.32-1.41 (m, 8H), 1.46-1.76





chloride
(m, 8H), 1.85 (dt, 2H), 3.10-3.21 (m, 6H), 4.01 (t,





2H), 7.38 (d, 2H), 7.75 (d, 2H)



172


1HNMR (CDCl3): 1.55 (s, 18H), 2.07 (tt, 2H),






2.25 (tt, 2H), 2.93 (t, 2H), 3.96 (t, 2H), 4.01 (t, 2H),





4.12 (t, 2H), 6.68 (dd, 2H), 6.84 (d, 2H), 7.26 (d,





2H), 7.77 (dd, 4H).



173
hydro-
Melting point 168-171° C.




chloride




174


1HNMR (CDCl3): 1.46 (s, 18H), 1.49 (s, 9H),






1.55 (s, 18H), 1.96 (tt, 4H), 3.50 (t, 4H), 3.63 (t,





4H), 4.49 (s, 4H), 7.32 (d, 4H), 7.77 (d, 4H).



175
hydro-

1HNMR (CD3OD): 1.91 (tt, 4H), 3.34 (t. 4H),





chloride
3.63 (t, 4H), 4.65 (s, 4H), 7.60 (d, 4H), 7.81 (d,





4H).



176


1HNMR (CDCl3): 1.09-1.24 (m, 6H), 1.40-1.67






(m, 58H), 2.02 (tt, 2H), 3.02 (t, 2H), 3.42 (t, 2H),





3.68 (t, 2H), 3.82 (t, 2H), 7.29 (d, 2H), 7.86 (d, 2H).



177
hydro-

1HNMR (CD3OD): 1.35-1.47 (m, 6H), 1.55-1.65





chloride
(m, 4H), 1.98 (tt, 2H), 3.14-3.23 (m, 6H), 3.37 (t,





2H), 7.52 (d, 2H), 7.74 (d, 2H).



178


1HNMR (CDCl3): 1.16-1.30 (m, 6H), 1.43-1.67






(m, 58H), 1.98 (tt, 2H), 3.47 (t, 2H), 3.53 (t, 2H),





3.63 (t, 2H), 3.84 (t, 2H), 4.53 (s, 2H), 7.38 (d, 2H),





7.87 (d, 2H).



179
hydro-

1HNMR (CD3OD): 1.33-1.49 (m, 6H), 1.53-1.65





chloride
(m, 4H), 1.92 (tt, 2H), 3.17 (t, 4H), 3.35 (t, 2H),





3.64 (t, 2H), 4.65 (s. 2H), 7.61 (d, 2H), 7.81 (d,





2H).



180


1HNMR (CDCl3): 1.55 (s, 18H), 2.09 (tt, 4H),






2.94 (tt, 4H), 4.02 (t, 2H), 8.88 (dd, 2H), 8.71 (s,





4H), 7.25 (d, 4H), 7.73 (d, 4H).









In the table, Boc or BOC indicates a t-butoxycarbonyl group. In the table, “-” means that a compound was synthesized as free form.










TABLE 85







Compound



No.
Structure





181


embedded image







182


embedded image







183


embedded image







184


embedded image







185


embedded image







186


embedded image







187


embedded image







188


embedded image







189


embedded image







190


embedded image
















Compound
Salt




No.
form
Physical property






181
hydro-
Melting point 169-172° C.




chloride




182


1HNMR(CDCl3): 1.16 (s, 9H), 1.92 (dt, 2H), 2.28






(dt, 2H), 3.60 (t, 2H), 3.70 (t, 2H), 3.99 (t, 2H),





4.23 (t, 2H), 6.62 (d, 1H), 6.75 (d, 1H), 6.83 (d,





2H), 7.43 (d, 2H)



183


1HNMR (CDCl3): 1.16 (s, 9H), 1.23-1.35 (m, 8H),






1.46-1.55 (m, 20H), 1.67-1.78 (m, 2H), 1.92 (dt,





2H), 2.23 (dt, 2H), 3.60 (t, 2H), 3.69 (t, 2H), 3.81-





3.91 (m, 4H), 3.95 (t, 2H), 4.12 (t, 2H), 6.81 (s,





2H), 6.83 (d, 2H), 7.48 (d, 2H)



184
hydro-

1HNMR (CD3OD): 1.33-1.44 (m, 8H), 1.54-1.63





chloride
(m, 2H), 1.69-1.79 (m, 2H), 2.1 0 (dt, 2H), 2.27 (dt,





2H), 3.16 (t, 2H), 353-3.62 (m, 4H), 3.86 (t, 2H),





4.09-4.18 (m, 4H), 6.96 (s, 2H), 7.12 (d, 2H), 7.62





(d, 2H)



185


1HNMR (CDCl3): 1.15-1.32 (m, 6H), 1.44-1.53






(m, 49H), 1.58-1.66 (m, 2H), 1.67-1.76 (m, 2H),





1.82 (dt, 2H), 3.47 (dd, 2H), 3.53 (dd, 2H), 3.83 (dd,





2H), 3.99 (t, 2H), 6.90 (d, 2H), 7.87 (d, 2H)



186
hydro-

1HNMR (CD3OD): 1.36-1.44 (m, 6H), 1.49-1.73





chloride
(m, 8H), 1.87 (dt, 2H), 3.15-3.24 (m, 6H), 4.11 (t,





2H), 7.11 (d, 2H), 7.78 (d, 2H)



187


1HNMR (CDCl3): 1.19-1.29 (m, 8H), 1.42-1.52






(m, 45H), 1.55 (s, 9H), 1.57-1.68 (m, 4H), 1.75-





1.89 (m, 4H), 3.23-3.38 (m, 2H), 3.48 (t, 2H), 3.60





(t, 2H), 4.00 (t, 2H), 6.88 (d, 2H), 7.87 (d, 2H).



188
hydro-

1HNMR (CD3OD): 1.33-1.47 (m, 8H), 1.52-1.61





chloride
(m, 4H), 1.73-1.97 (m, 4H), 3.12-3.24 (m, 4H),





3.26-3.33 (m, 2H), 4.15 (t, 2H), 7.14 (d, 2H), 7.81





(d, 2H).



189


1HNMR (CDCl3): 1.15 (s, 9H), 1.22-1.38 (m, 6H),






1.45-1.53 (m, 47H), 1.63-1.71 (m, 2H), 1.92 (tt,





2H), 2.18 (dt, 2H), 3.49 (dd, 2H), 3.59 (t, 2H), 3.67





(t, 2H), 3.72 (t, 2H), 3.87 (dt, 2H), 4.01 (t, 2H),





6.83 (d, 2H), 7.40 (d, 2H)



190
hydro-

1HNMR (CD3OD): 1.36-1.46 (m, 6H), 1.53-1.68





chloride
(m, 4H), 2.05-2.16 (m, 4H), 3.19 (dd, 4H), 3.42 (t,





2H), 3.54-3.61 (m, 4H), 4.18 (t, 2H), 7.15 (d, 2H),





7.67 (d, 2H)









In the table, Boc or BOC indicates a t-butoxycarbonyl group. In the table, “-” means that a compound was synthesized as free form.










TABLE 86







Compound



No.
Structure





191


embedded image







192


embedded image







193


embedded image







194


embedded image







195


embedded image







196


embedded image







197


embedded image







198


embedded image







199


embedded image







200


embedded image
















Compound
Salt




No.
form
Physical property






191


1HNMR (CDCl3): 1.15 (s, 9H), 1.20-1.37 (m, 8H),






1.46-1.55 (m, 47H), 1.60-1.70 (m, 2H), 1.92 (tt,





2H), 2.16 (dt, 2H), 3.38 (dd, 2H), 3.48 (dd, 2H),





3.59 (t, 2H), 3.66-3.76 (m, 4H), 4.01 (t, 2H), 6.85





(d, 2H), 7.40 (d, 2H)



192
hydro-

1HNMR (CD3OD): 1.35-1.43 (m, 8H), 1.54-1.64





chloride
(m, 4H), 2.05-2.15 (m, 4H), 3.17 (dd, 4H), 3.42 (t,





2H), 3.54-3.61 (m, 4H), 4.18 (t, 2H), 7.15 (d, 2H),





7.67 (d, 2H)



193


1HNMR (CDCl3): 1.43-1.58 (m, 45H), 1.69-1.89






(m, 8H), 3.51-3.67 (m, 4H), 3.94 (t, 2H), 4.26 (t,





2H), 6.61 (dd, 1H), 6.78 (d, 2H), 7.74 (d, 2H), 8.03





(ddd, 1H), 8.52 (d, 1H).



194
hydro-

1HNMR (CD3OD): 1.69-1.99 (m, 8H), 3.27-3.34





chloride
(m, 4H), 4.05-4.24 (m, 2H), 4.40-4.53 (m, 2H),





6.88 (d, 1H), 7.14 (d, 2H), 7.50-7.69 (m, 1H), 7.79





(d, 2H), 8.07 (d, 1H).



195


1HNMR (CDCl3): 1.42-1.60 (m, 45H), 1.70-1.86






(m, 4H), 2.10 (tt, 2H), 2.79 (t, 2H), 3.60 (t, 2H),





3.65 (t, 2H), 3.88 (t, 2H), 6.38 (s, 1H), 6.72 (d, 2H),





7.30 (d, 1H), 7.66 (dd, 1H), 7.73 (d, 2H), 7.96 (d,





1H).



196
hydro-

1HNMR (D2O): 1.36-1.48 (m, 2H), 1.51-1.62 (m,





chloride
2H), 1.88 (tt, 2H), 2.73 (t, 2H), 2.88-2.99 (m, 2H),





3.15 (t, 2H), 3.91 (t, 2H), 6.52 (s, 1H), 6.91 (d, 2H),





7.44 (d, 2H), 7.53 (d, 2H), 7.78 (dd, 1H).



197


1HNMR (CDCl3): 1.19-1.31 (m, 8H), 1.40-1.65






(m, 58H), 2.03 (tt, 2H), 3.02 (t, 2H), 3.35 (q, 2H),





3.45 (t, 2H), 3.67 (t, 2H), 7.29 (d, 2H), 7.80 (d, 2H).



198
hydro-

1HNMR (CD3OD): 1.35-1.44 (m, 8H), 1.53-1.65





chloride
(m, 4H), 1.98 (tt, 2H), 3.13-3.22 (m, 6H), 3.37 (t,





2H), 7.52 (d, 2H), 7.74 (d, 2H).



199


1HNMR (CDCl3): 1.09-1.30 (m, 8H), 1.43-1.62






(m, 58H), 3.33 (q, 2H), 3.43 (t, 2H), 3.71 (t, 2H),





3.84 (t, 2H), 4.55 (s, 2H), 7.38 (d, 2H), 7.88 (d,





2H).



200
hydro-

1HNMR (CD3OD): 1.31-1.44 (m, 8H), 1.52-1.64





chloride
(m, 4H), 3.13-3.22 (m, 4H), 3.47 (t, 2H), 3.69 (t,





2H), 4.70 (s, 2H), 7.62 (d, 2H), 7.82 (d, 2H).









In the table, Boc or BOC indicates a t-butoxycarbonyl group. In the table, “-” means that a compound was synthesized as free form.










TABLE 87







Compound



No.
Structure





201


embedded image







202


embedded image







203


embedded image







204


embedded image







205


embedded image







206


embedded image







207


embedded image







208


embedded image







209


embedded image







210


embedded image
















Compound
Salt




No.
form
Physical property






201


1HNMR (CDCl3): 1.15 (s, 9H), 1.24-1.38 (m, 6H),






1.44-1.57 (m, 47H), 1.62-1.70 (m, 2H), 1.74-1.87





(m, 4H), 1.92 (tt, 2H), 3.49 (dt, 2H), 3.54-3.61 (m,





4H), 3.69 (t, 2H), 3.87 (dt, 2H), 3.98 (t, 2H), 6.82





(d, 2H), 7.40 (d, 2H)



202
hydro-

1HNMR (CD3OD): 1.37-1.45 (m, 6H), 1.54-1.68





chloride
(m, 4H), 1.75-1.83 (m, 2H), 1.83-1.88 (m, 2H),





2.10 (tt, 2H), 3.14-3.22 (m, 4H), 3.33-3.40 (m,





2H), 3.57 (t, 4H), 4.12 (t, 2H), 7.12 (d, 2H), 7.66 (d,





2H)



203


1HNMR (CDCl3): 1.14 (s, 9H), 1.23-1.35 (m, 8H),






1.45-1.55 (m, 47H), 1.62-1.69 (m, 2H), 1.70-1.81





(m, 4H), 1.92 (tt, 2H), 3.39 (tt, 2H), 3.49 (dt, 2H),





3.55-3.63 (m, 4H), 3.69 (t, 2H), 3.98 (t, 2H), 6.82





(d, 2H), 7.40 (d, 2H)



204
hydro-

1HNMR (CD3OD): 1.35-1.44 (m, 8H), 1.54-1.66





chloride
(m, 4H), 1.69-1.79 (m, 2H), 1.80-1.88 (m, 2H),





2.10 (tt, 2H), 3.17 (tt, 4H), 3.32-3.39 (m, 2H),





3.57 (t, 4H), 4.12 (t, 2H), 7.14 (d, 2H), 7.67 (d, 2H)



205


1HNMR (CDCl3): 1.16 (s, 9H), 1.24-1.39 (m, 6H),






1.46-1.63 (m, 20H), 1.69-1.79 (m, 2H), 1.92 (tt,





2H), 2.23 (tt, 2H), 3.60 (t, 2H), 3.69 (t, 2H), 3.80-





3.79 (m, 4H), 3.95 (t, 2H), 4.12 (t, 2H), 6.69 (s,





2H), 6.84 (d, 2H), 7.42 (d, 2H)



206
hydro-

1HNMR (CD3OD): 1.34-1.44 (m, 6H), 1.54-1.67





chloride
(m, 2H), 1.69-1.80 (m, 2H), 2.10 (tt, 2H), 2.26 (tt,





2H), 3.17 (t, 2H), 3.54-3.61 (m, 4H), 3.86 (t, 2H),





4.09-4.18 (m, 4H), 6.97 (d, 2H), 7.12 (d, 2H), 7.68





(d, 2H)



207


1HNMR (CDCl3): 1.16 (s, 9H), 1.19-1.33 (m, 6H),






1.47-1.58 (m, 20H), 1.70-1.83 (m, 4H), 1.86-2.02





(m, 4H), 3.60 (t, 2H), 3.69 (t, 2H), 3.82-3.90 (m,





4H), 3.95 (t, 2H), 3.99 (t, 2H), 6.76 (d, 2H), 6.83 (d,





2H), 7.41 (d, 2H)



208
hydro-

1HNMR (CD3OD): 1.35-1.46 (m, 6H), 1.54-1.66





chloride
(m, 2H), 1.72-1.81 (m, 2H), 1.82-2.01 (m, 4H),





2.09 (tt, 2H), 3.17 (t, 2H), 3.53-3.61 (m, 4H), 3.88





(t, 2H), 3.97 (t, 2H), 4.13 (t, 2H), 6.99 (d, 2H), 7.12





(d, 2H), 7.66 (d, 2H)



209


1HNMR (CDCl3): 1.16 (s, 9H), 1.24-1.34 (m, 8H),






1.43-1.57 (m, 20H), 1.69-1.84 (m, 4H), 1.84-2.03





(m, 4H), 3.59 (t, 2H), 3.69 (t, 2H), 3.83-3.91 (m,





4H), 3.95 (t, 2H), 3.99 (t, 2H), 6.75 (d, 2H), 6.83 (d,





2H), 7.41 (d, 2H)



210
hydro-

1HNMR (CD3OD): 1.33-1.43 (m, 8H), 1.54-1.63





chloride
(m, 2H), 1.69-1.80 (m, 2H), 1.83-2.00 (m, 4H),





2.09 (tt, 2H), 3.17 (t, 2H), 3.54-3.51 (m, 4H), 3.85





(t, 2H), 3.97 (t, 2H), 4.13 (t, 2H), 6.99 (d, 2H), 7.11





(d, 2H), 7.67 (d, 2H)









In the table, Boc or BOC indicates a t-butoxycarbonyl group. In the table, “-” means that a compound was synthesized as free form.










TABLE 88







Compound



No.
Structure





211


embedded image







212


embedded image







213


embedded image







214


embedded image







215


embedded image







216


embedded image







217


embedded image







218


embedded image







219


embedded image







220


embedded image
















Compound
Salt




No.
form
Physical property






211


1HNMR (CDCl3): 1.16 (s, 9H), 1.22-1.35 (m,






10H), 1.45-1.57 (m, 20H), 1.71-1.84 (m, 4H),





1.89-2.02 (m, 4H), 3.59 (t, 2H), 3.69 (t, 2H), 3.83-





3.90 (m, 4H), 3.92-4.02 (m, 4H), 6.75 (d, 2H), 6.33





(d, 2H), 7 41 (d, 2H)



212
hydro-

1HNMR (CD3OD): 1.30-1.42 (m, 10H), 1.52-1.63





chloride
(m, 2H), 1.69-1.80 (m, 2H), 1.82-2.00 (m, 4H),





2.09 (tt, 2H), 3.16 (t, 2H), 3.54-3.60 (m, 4H), 3.87





(t, 2H), 3.97 (t, 2H), 4.13 (t, 2H), 6.99 (d, 2H), 7.19





(d, 2H), 7.66 (d, 2H)



213


1HNMR (CDCl3): 1.16 (s, 9H), 1.55 (s, 9H),






1.74-1.87 (m, 4H), 1.88-2.02 (m, 6H), 3.59 (t, 2H),





3.69 (t, 2H), 3.93-4.04 (m, 8H), 6.78 (s, 2H), 6.85





(d, 2H), 6.89 (d, 2H), 7.41 (d, 2H), 7.82 (d, 2H)



214
hydro-

1HNMR (CD3OD): 1.84-2.03 (m, 8H), 2.06-2.14





chloride
(m, 2H), 3.54-3.62 (m, 4H), 3.93-4.03 (m, 4H),





4.10-4.20 (m, 4H), 7.02 (s, 2H), 7.13 (dd, 4H), 7.70





(d, 2H), 7.80 (d, 2H)



215


1HNMR (CDCl3): 1.21-1.35 (m, 8H), 1.47-1.59






(m, 29H), 1.67-1.85 (m, 4H), 1.97 (tt, 2H), 3.80-





3.90 (m, 4H), 3.95 (t, 2H), 4.01 (t, 2H), 6.74 (d,





1H), 6.77 (d, 1H), 6.88 (d, 2H), 7.84 (d, 2H).



216
hydro-

1HNMR (CD3OD): 1.31-1.45 (m, 8H), 1.59 (tt,





chloride
2H), 1.75 (tt, 2H), 1.83-2.03 (m, 4H), 3.16 (t, 2H),





3.88 (t, 2H), 3.98 (t, 2H), 4.15 (t, 2H), 6.78 (d, 1H),





7.01 (d, 1H), 7.13 (d, 2H), 7.80 (d, 2H).



217


1HNMR (CDCl3): 1.65 (s, 9H), 1.20-1.30 (m,






12H), 1.45-1.54 (m, 45H), 1.64-1.70 (m, 2H), 1.91





(tt, 2H), 2.16 (tt, 2H), 3.49 (dd, 2H), 3.58 (dd, 2H),





3.69 (t, 2H), 3.73 (t, 2H), 3.88 (dd, 2H), 4.01 (t,





2H), 6.83 (d, 2H), 7.40 (d, 2H)



218
hydro-

1HNMR (CD3OD): 1.32-1.44 (m, 10H), 1.53-1.65





chloride
(m, 4H), 2.06-2.11 (m, 4H), 3.13-3.21 (m, 4H),





3.42 (t, 2H), 3.57 (t, 4H), 4.17 (t, 2H), 7.15 (d, 2H),





7.67 (d, 2H)



219


1HNMR (CDCl3): 1.11 (s, 9H), 1.18-1.35 (m,






8H), 1.41-1.68 (m, 49H), 1.92 (tt, 2H), 3.35-3.42





(m, 2H), 3.46 (dd, 2H), 3.62 (t, 2H), 3.65-3.73 (m,





4H), 3.81 (dd, 2H), 4.53 (s, 2H), 7.29 (d, 2H), 7.44





(d, 2H).



220
hydro-

1HNMR (CD3OD): 1.33-1.44 (m, 8H), 1.53-1.64





chloride
(m, 4H), 2.12 (tt, 2H), 3.14-3.22 (m, 4H), 3.46 (t,





2H), 357-3.63 (m, 4H), 3.68 (t, 2H), 4.69 (s, 2H),





7.60 (d, 2H), 7.72 (d, 2H).









In the table, Boc or BOC indicates a t-butoxycarbonyl group. In the table, “-” means that a compound was synthesized as free form.










TABLE 89







Compound



No.
Structure





221


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222


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223


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224


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225


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226


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227


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228


embedded image







229


embedded image







230


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Compound
Salt




No.
form
Physical property






221


1HNMR (CDCl3): 1.11 (s, 9H), 1.22-1.35 (m,






8H), 1.43-1.69 (m, 49H), 1.88-2.01 (m, 4H), 3.39





(q, 2H), 3.44-3.51 (m, 4H), 3.59-3.66 (m, 4H), 3.71





(t, 2H), 4.51 (s, 2H), 7.28 (d, 2H), 7.44 (d, 2H).



222
hydro-

1HNMR (CD3OD): 1.35-1.44 (m, 8H), 1.53-1.63





chloride
(m, 4H), 1.91 (tt, 2H), 2.12 (tt, 2H), 3.17 (t, 4H),





3.34 (t, 2H), 3.56-3.65 (m, 6H), 4.64 (s, 2H), 7.59





(d, 2H), 7.71 (d, 2H).



223


1HNMR (CDCl3): 1.11 (s, 9H), 1.21-1.35 (m,






6H), 1.44-1.70 (m, 49H), 1.87-2.01 (m, 4H), 3.44-





3.51 (m, 4H), 3.59-3.65 (m, 4H), 3.71 (t, 2H), 3.87





(dd, 2H), 4.51 (s, 2H), 7.28 (d, 2H), 7.44 (d, 2H).



224
hydro-

1HNMR (CD3OD): 1.37-1.44 (m, 6H), 1.54-1.64





chloride
(m, 4H), 1.91 (tt, 2H), 2.12 (tt, 2H), 3.14-3.20 (m,





4H), 3.34 (t, 2H), 3.58-3.65 (m, 6H), 4.64 (s, 2H),





7.59 (d, 2H), 7.71 (d, 2H).



225


1HNMR (CDCl3): 1.46 (s, 18H), 1.51 (s, 9H),






1.56 (s, 18H), 3.66 (t, 4H), 3.79 (t, 4H), 4.44 (s,





4H), 7.22 (d, 4H), 7.71 (d, 4H).



226
hydro-
Melting point 262-267° C.




chloride




227


1HNMR (CDCl3): 0.88-1.08 (m, 6H), 1.38-1.58






(m, 58H), 3.51 (dd, 2H), 3.73 (t, 2H), 3.77 (dd,





2H), 3.87 (t, 2H), 4.54 (s, 2H), 7.37 (d, 2H), 8.00





(d, 2H).



228
hydro-

1HNMR (CD3OD): 1.36-1.43 (m, 6H), 1.55-1.65





chloride
(m, 4H), 3.14-3.22 (m, 4H), 3.47 (t, 2H), 3.69 (t,





2H), 4.70 (s, 2H), 7.62 (d, 2H), 7.82 (d, 2H).



229


1HNMR (CDCl3): 1.16-1.31 (m, 8H), 1.42-1.57






(m, 58H), 2.16 (tt, 2H), 3.30-3.40 (m, 2H), 3.47 (t,





2H), 3.73 (t, 2H), 4.06 (t, 2H), 6.90 (d, 2H), 7.87 (d,





2H).



230
hydro-

1HNMR (CD3OD): 1.31-1.45 (m, 8H), 1.50-1.68





chloride
(m, 4H), 2.11 (tt, 2H), 3.10-3.27 (m, 4H), 3.44 (t,





2H), 4.20 (t, 2H), 7.17 (d, 2H), 7.81 (d, 2H).









In the table, Boc or BOC indicates a t-butoxycarbonyl group. In the table, “-” means that a compound was synthesized as free form.










TABLE 90







Compound



No.
Structure





231


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232


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233


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234


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235


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236


embedded image







237


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238


embedded image







239


embedded image







240


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Compound
Salt




No.
form
Physical property






231


1HNMR (CDCl3): 1.09 (m, 8H), 1.40-1.65






(m, 58H), 3.30 (td, 2H), 3.46 (t, 2H), 4.03 (t, 2H),





4.20 (t, 2H), 6.91 (d, 2H), 7.93 (d, 2H).



232
hydro-

1HNMR (CD3OD): 1.31-1.46 (m, 8H), 1.50-1.67





chloride
(m, 4H), 3.17 (t, 2H), 3.21 (t, 2H), 3.69 (t, 2H),





4.25 (t, 2H), 7.19 (d, 2H), 7.45 (d, 2H).



233


1HNMR (CDCl3): 1.07 (m, 10H), 1.40-1.57






(m, 58H), 3.47 (t, 2H), 3.84 (t, 2H), 4.02 (t, 2H),





4.21 (t, 2H), 6.91 (d, 2H), 7.92 (d, 2H).



234
hydro-

1HNMR (CD3OD): 1.30-1.45 (m, 20H), 1.51-1.67





chloride
(m, 4H), 3.16 (t, 2H), 3.21 (t, 2H), 3.69 (t, 2H),





4.25 (t, 2H), 7.19 (d, 2H), 7.82 (d, 2H).



235


1HNMR (CDCl3): 0.93 (m, 6H), 1.33-1.68 (m,






58H), 3.41 (t, 2H), 3.76 (t, 2H), 4.08 (t, 2H), 4.19





(t, 2H), 6.90 (d, 2H), 7.99 (d, 2H).



236
hydro-

1HNMR (CD3OD): 1.34-1.47 (m, 6H), 1.53-1.68





chloride
(m, 4H), 3.11-3.27 (m, 4H), 3.67 (t, 2H), 4.25 (t,





2H), 7.19 (d, 2H), 7.83 (d, 2H).



237


1HNMR (CDCl3): 1.11 (s, 9H), 1.20-1.36 (m,






6H, 1.44-1.69 (m, 49H), 1.92 (tt, 2H), 3.47 (dd,





2H), 3.62 (t, 2H), 3.65-3.73 (m, 4H), 3.80 (t, 2H),





3.87 (t, 2H), 4.53 (s, 2H), 7.29 (d, 2H), 7.44 (d,





2H).



238
hydro-

1HNMR (CD3OD): 1.37-1.45 (m, 6H), 1.54-1.65





chloride
(m, 4H), 2.12 (tt, 2H), 3.14-3.22 (m, 4H), 3.46





2H), 3.57-3.63 (m, 4H), 3.68 (t, 2H), 4.69 (s, 2H),





7.60 (d, 2H), 7.71 (d, 2H).



239


1HNMR (CDCl3): 1.14 (s, 9H), 1.20-1.38 (m, 8H),






1.44-1.52 (m, 47H), 1.62-1.70 (m, 2H), 1.88-1.95





(m, 2H), 3.34-3.42 (m, 2H), 3.45-3.54 (m, 2H),





3.58 (t, 2H), 3.68 (t, 2H), 3.96 (dd, 2H), 4.20 (dd,





2H), 6.85 (d, 2H), 7.40 (d, 2H)



240
hydro-

1HNMR (CD3OD): 1.35-1.44 (m, 8H), 1.54-1.68





chloride
(m, 4H), 2.10 (tt, 2H), 3.14-3.24 (m, 4H), 3.58 (dd,





4H), 3.68 (t, 2H), 4.22 (t, 2H), 7.17 (d, 2H), 7.69 (d,





2H)









In the table, Boc or BOC indicates a t-butoxycarbonyl group. In the table, “-” means that a compound was synthesized as free form.










TABLE 91







Compound



No.
Structure





241


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242


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243


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244


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245


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246


embedded image







247


embedded image







248


embedded image







249


embedded image







250


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Compound
Salt




No.
form
Physical property






241


1HNMR (CDCl3): 1.15 (s, 9H), 1.23-1.34 (m,






10H), 1.44-1.54 (m, 47H), 1.62-1.72 (m, 2H), 1.91





(tt, 2H), 3.45-3.53 (m, 2H), 3.59 (dd, 2H), 3.68 (t,





2H), 3.88 (dd, 2H), 3.95 (dd, 2H), 4.19 (t, 2H), 6.85





(d, 2H), 7.40 (d, 2H)



242
hydro-

1HNMR (CD3OD): 1.34-1.42 (m, 10H), 1.55-1.66





chloride
(m, 4H), 2.10 (tt, 2H), 3.14-3.22 (m, 4H), 3.58 (dd,





4H), 3.69 (t, 2H), 4.22 (dd, 2H), 7.17 (d, 2H), 7.69





(d, 2H)



243


1HNMR (CDCl3): 1.25-1.34 (m, 15H), 1.46-1.54






(m, 45H), 1.52-1.72 (m, 2H), 1.76-1.90 (m, 4H),





3.49 (dd, 2H), 3.57 (dd, 2H), 3.85-4.03 (m, 8H),





6.84 (d, 2H), 7.45 (d, 2H)



244
hydro-

1HNMR (CD3OD): 1.32-1.50 (m, 6H), 1.52-1.64





chloride
(m, 4H), 1.76-1.98 (m, 4H), 3.25-332 (m, 4H),





4.26-4.32 (m, 2H), 4.06 (s, 4H), 4.15 (t, 2H), 7.15





(d, 2H), 7.84 (d, 2H)



245


1HNMR (CDCl3): 1.25-1.34 (m, 18H), 1.46-1.54






(m, 45H), 1.55-1.64 (m, 4H), 1.76-1.90 (m, 4H),





3.39 (dd, 2H), 3.49 (dd, 2H), 3.58 (dd, 2H), 3.88-





4.02 (m, 6H), 6.84 (d, 2H), 7.45 (d, 2H)



246
hydro-

1HNMR (CD3OD): 1.32-1.54 (m, 8H), 1.51-1.61





chloride
(m, 4H), 1.75-1.97 (m, 4H), 3.25-3.29 (m, 4H),





4.23-4.30 (m, 2H), 4.05 (s, 4H), 4.14 (t, 2H), 7.15





(d, 2H), 7.84 (d, 2H)



247


1HNMR (CDCl3): 1.15 (s, 9H), 1.21-1.36 (m, 8H),






1.40-1.85 (m, 55H), 1.91 (tt, 2H), 3.39 (q, 2H),





3.44-3.56 (m, 4H), 3.59 (t, 2H), 3.69 (t, 2H), 3.96





(t, 2H), 6.84 (d, 2H), 7.41 (d, 2H)



248
hydro-

1HNMR (CD3OD): 1.34-1.45 (m, 8H), 1.52-1.73





chloride
(m, 8H), 1.85 (tt, 2H), 2.09 (tt, 2H), 3.13-3.25 (m,





6H), 3.55-3.61 (m, 4H), 4.10 (t, 2H), 7.11 (d, 2H),





7.66 (d, 2H).



249


1HNMR (CDCl3): 1.16 (s, 9H), 1.22-1.33 (m, 8H),






1.44-1.70 (m, 49H), 1.91-2.06 (m, 4H), 3.48 (t,





2H), 3.59 (t, 2H), 3.64-3.69 (m, 4H), 3.74 (t, 2H),





3.38 (t, 2H), 4.64 (s, 2H), 7.43 (d, 1H), 7.79 (dd,





1H), 8.61 (d, 1H).



250
hydro-

1HNMR (CD3OD): 1.34-1.44 (m, 8H), 1.54-1.65





chloride
(m, 4H), 1.93 (tt, 2H), 2.12 (tt, 2H), 3.14-3.22 (m,





4H), 3.40 (t, 2H), 3.63-3.69 (m, 4H), 3.80 (t, 2H),





4.98 (s, 2H), 8.12 (d, 1H), 8.66 (dd, 1H), 9.13 (d,





1H).









In the table, Boc or BOC indicates a t-butoxycarbonyl group. In the table, “-” means that a compound was synthesized as free form.










TABLE 92







Compound



No.
Structure





251


embedded image







252


embedded image







253


embedded image







254


embedded image







255


embedded image







256


embedded image







257


embedded image







258


embedded image







259


embedded image







260


embedded image
















Compound
Salt




No.
form
Physical property






251


1HNMR (CDCl3): 1.10 (s, 9H), 1.19-1.38 (m, 8H),






1.42-1.69 (m, 49H), 1.87-2.04 (m, 4H), 2.64 (t,





2H), 3.39 (tt, 2H), 3.47 (dd, 2H), 3.55 (dd, 2H), 3.60





(t, 2H), 3.70 (t, 2H), 7.16 (d, 2H), 7.38 (d, 2H).



252
trifluoro-

1HNMR (CD3OD): 1.10 (s, 9H), 1.19-1.38 (m,





acetate
8H), 1.42-1.69 (m, 49H), 1.87-2.04 (m, 4H), 2.64





(t, 2H), 3.39 (tt, 2H), 3.47 (dd, 2H), 3.55 (dd, 2H),





3.60 (t, 2H), 3.70 (t, 2H), 7.16 (d, 2H), 7.38 (d, 2H)



253


1HNMR (CD3OD): 1.06-1.89 (m, 74H), 3.37-4.08






(m, 12H), 6.95 (d, 2H), 7.55 (d, 2H)



254
hydro-

1HNMR (CD3OD): 1.34-1.45 (m, 8H), 1.54-1.65





chloride
(m, 4H), 1.74-1.93 (m, 4H), 2.04-2.10 (m, 4H),





3.14-3.21 (m, 4H), 3.28 (t, 2H), 3.69-3.77 (m, 4H),





4.13 (t, 2H), 7.11 (d, 2H), 7.63 (d, 2H).



255


1HNMR (CD3OD): 1.26-1.38 (m, 23H), 1.43-1.69






(m, 45H), 1.75-1.89 (m, 4H), 3.49 (t, 2H), 3.58 (t,





2H), 3.72 (s, 2H), 3.85 (t, 2H), 4.04 (t, 2H), 3.73 (t,





2H), 338 (t, 2H), 6.94 (d, 2H), 7.41 (d, 2H).



256
hydro-

1HNMR (CD3OD): 1.34-1.45 (m, 8H), 1.53 (s,





chloride
6H), 1.55-1.65 (m, 4H), 1.75-1.94 (m, 4H), 3.14-





3.21 (m, 4H), 3.28 (t, 2H), 3.82 (s, 2H), 4.16 (t,





2H), 7.16 (d, 2H), 7.85 (d, 2H).



257


1HNMR (CD3OD): 1.00 (s, 6H), 1.13 (s, 9H),






1.25-1.38 (m, 8H), 1.44-1.69 (m, 49H), 3.45 (s,





2H), 3.46-3.53 (m, 2H), 3.58 (t, 2H), 3.85 (t, 2H),





4.04 (t, 2H), 3.73 (t, 2H), 3.88 (t, 2H), 6.93 (d, 2H),





7.36 (d, 2H).



258
hydro-

1HNMR (CD3OD): 1.13 (s, 6H), 1.35-1.43 (m,





chloride
8H), 1.54-1.65 (m, 4H), 1.75-1.93 (m, 4H), 3.14-





3.21 (m, 4H), 3.25-3.29 (m, 6H), 4.13 (t, 2H), 7.13





(d, 2H), 7.69 (d, 2H)



259


1HNMR (CDCl3): 1.06 (s, 9H), 1.23-1.33 (m,






8H), 1.42-1.69 (m, 53H), 1.94 (tt, 2H), 2.12 (tt, 2H),





2.79 (t, 2H), 3.48 (t, 2H), 3.59-3.65 (m, 4H), 3.73





(t, 2H), 3.88 (t, 2H), 6.40 (s, 1H), 7.30-7.38 (m,





2H), 7.51 (d, 1H).



260
hydro-

1HNMR (CD3OD): 1.33-1.46 (m, 8H), 1.53-1.64





chloride
(m, 4H), 2.06 (tt, 2H), 2.13 (tt, 2H), 2.94 (t, 2H),





3.12-3.21 (m, 4H), 3.58-3.64 (m, 4H), 6.73 (s, 1H),





7.56 (dd, 1H), 7.63 (d, 1H), 7.92 (d, 1H).









In the table, Boc or BOC indicates a t-butoxycarbonyl group. In the table, “-” means that a compound was synthesized as free form.










TABLE 93







Compound



No.
Structure





261


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262


embedded image







263


embedded image







264


embedded image







265


embedded image







266


embedded image







267


embedded image







268


embedded image







269


embedded image







270


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Compound
Salt




No.
form
Physical property






261


1HNMR (CDCl3): 1.11 (s, 9H), 1.14-1.29 (m, 8H),






1.38 (s, 9H), 1.45-1.62 (m, 40H), 1.92 (tt, 2H),





3.30 (m, 2H), 3.61 (t, 2H), 3.70 (t, 2H), 3.86 (t,





2H), 4.86 (s, 2H), 7.35 (d, 2H), 7.43 (d, 2H)



262
hydro-

1HNMR (CD3OD): 1.34-1.45 (m, 8H), 1.54-1.67





chloride
(m, 4H), 2.12 (tt, 2H), 3.17 (t, 2H), 3.22 (t, 2H),





3.60 (t, 4H), 4.57 (s, 2H), 7.57 (d, 2H), 7.75 (d,





2H).



263


1HNMR (CDCl3): 1.15 (s, 9H), 1.20-1.39 (m, 8H),






1.45-2.10 (m, 46H), 3.35-3.90 (m, 12H), 4.61 (m,





1H), 6.88 (d, 2H), 7.43 (d, 2H)



264
hydro-

1HNMR (CD3OD): 1.35-1.44 (m, 8H), 1.50-1.69





chloride
(m, 4H), 1.79-1.99 (m, 2H), 2.05-2.16 (m, 4H),





3.13-3.20 (m, 2H), 3.21-3.29 (m, 2H), 3.45-3.53





(m, 2H), 3.55-3.60 (m, 4H), 3.65-3.74 (m, 2H),





4.81-4.89 (m, 1H), 7.18 (d, 2H), 7.68 (d, 2H)



265


1HNMR (CDCl3): 1.09 (s, 9H), 1.22-1.35 (m, 8H),






1.44-1.69 (m, 49H), 1.92 (tt, 2H), 2.99 (dd, 2H),





3.53 (t, 2H), 3.58-3.68 (m, 4H), 3.70 (t, 2H), 3.88





(t, 2H), 7.19 (d, 2H), 7.40 (d, 2H)



266
hydro-

1HNMR (CD3OD): 1.33-1.43 (m, 8H), 1.50-1.64





chloride
(m, 4H), 2.11 (tt, 2H), 3.00 (t, 2H), 3.10-3.20 (m,





4H), 3.51 (t, 2H), 3.56-3.62 (m, 4H), 7.52 (d, 2H),





7.68 (d, 2H)



267


1HNMR (CDCl3): 1.05 (s, 9H), 1.10-1.65 (m,






57H), 1.94 (tt, 2H), 3.33-3.43 (m, 4H), 3.63 (t, 2H),





3.73 (t, 2H), 4.96 (s, 2H), 6.73 (s, 1H), 7.34-7.42





(m, 2H), 7.66 (d, 1H)



268
hydro-

1HNMR (CDCl3): 1.17 (s, 9H), 1.22-1.37 (m, 8H),





chloride
(m, 4H), 2.13 (tt, 2H), 3.13-3.19 (m, 2H), 3.20-





3.27 (m, 2H), 3.59-3.65 (m, 4H), 4.66-4.69 (m,





2H), 6.97 (s, 1H), 7.63-7.73 (m, 2H). 8.00 (d, 1H)



269


1HNMR (CDCl3): 1.17 (s, 9H), 1.23-1.37 (m, 8H),






1.44-1.61 (m, 20H), 1.67-1.80 (m, 2H), 1.92 (tt,





2H), 3.60 (t, 2H), 3.69 (t, 2H), 3.81-3.93 (m, 4H),





4.25 (t, 2H), 4.32 (t, 2H), 6.73 (d, 1H), 6.65 (d, 2H),





6.99 (d, 1H), 7.43 (d, 2H).



270
hydro-

1HNMR (CD3OD): 1.30-1.43 (m, 8H), 1.57 (tt,





chloride
2H), 1.74 (tt, 2H), 2.09 (tt, 2H), 3.16 (t, 2H), 3.54-





3.61 (m, 4H), 3.88 (t, 2H), 4.32-4.43 (m, 4H), 6.98





(d, 1H), 7.06 (d, 1H), 7.13 (d, 2H), 7.69 (d, 2H).









In the table, Boc or BOC indicates a t-butoxycarbonyl group. In the table, “-” means that a compound was synthesized as free form.










TABLE 94







Compound



No.
Structure





271


embedded image







272


embedded image







273


embedded image







274


embedded image







275


embedded image







276


embedded image







277


embedded image







278


embedded image







279


embedded image







280


embedded image
















Compound
Salt




No.
form
Physical property






271
hydro-

1HNMR (CD3OD): 1.32-1.46 (m, 8H), 1.53-1.67





chloride
(m, 4H), 1.93 (tt, 2H), 2.11 (tt, 2H), 2.80 (t, 2H),





3.12-3.22 (m, 4H), 3.25 (t, 2H), 3.54-3.63 (m, 4H),





7.49 (d, 2H), 7.65 (d, 2H).



272


1HNMR (CDCl3): 1.14 (s, 9H), 1.21-1.34 (m, 8H),






1.45-1.57 (m, 47H), 1.61-1.70 (m, 2H), 1.94 (dt,





2H), 2.08 (dt, 2H), 2.83 (dd, 2H), 3.46 (dd, 2H),





3.56-3.66 (m, 4H), 3.73 (dd, 2H), 3.87 (dd, 2H),





7.21 (d, 1H), 7.69 (dd, 1H), 8.57 (d, 1H)



273
hydro-

1HNMR (CD3OD): 1.33-1.44 (m, 10H), 1.54-1.67





chloride
(m, 4H), 2.05 (dt, 2H), 2.14 (dt, 2H), 3.02 (dd, 2H),





3.13-3.22 (m, 4H), 3.60-3.65 (m, 4H), 7.69 (d, 1H),





8.20 (dd, 1H), 8.88 (d, 1H)



274


1HNMR (CDCl3): 1.20 (s, 9H), 1.21-1.35 (m, 8H),






1.44-1.58 (m, 47H), 1.62-1.66 (m, 2H), 1.74-1.85





(m, 4H), 1.93 (dt, 2H), 3.49 (dd, 2H), 3.58 (dd, 2H),





3.62 (t, 2H), 3.71 (t, 2H), 3.88 (dd, 2H), 4.30 (dd,





2H), 3.68 (d, 1H), 7.68 (dd, 1H), 8.22 (d, 1H)



275
hydro-

1HNMR (CD3OD): 1.35-1.44 (m, 8H), 1.53-1.65





chloride
(m, 4H), 1.72-1.79 (m, 2H), 1.84-1.90 (m, 2H),





2.11 (dt, 2H), 3.17 (dd, 4H), 3.27 (dd, 2H), 3.59 (dd,





4H), 4.43 (t, 2H), 6.96 (d, 1H), 7.95 (dd, 1H), 8.52





(d, 1H)



276


1HNMR (CDCl3): 1.17 (s, 9H), 1.23-1.36 (m, 6H),






1.41-1.53 (m, 58H), 1.62-1.71 (m, 2H), 1.75-1.87





(m, 4H), 3.46-3.61 (m, 3H), 3.69-3.74 (m, 1H),





3.80-389 (m, 4H), 3.98 (dd, 2H), 4.68-4.73 (m,





1H), 6.84 (d, 2H), 7.42 (d, 2H)



277
hydro-

1HNMR (CD3OD): 1.36-1.45 (m, 6H), 1.55-1.65





chloride
(m, 4H), 1.75-1.94 (m, 4H), 3.14-3.24 (m, 4H),





3.44 (t, 2H), 3.77 (dd, 2H), 3.96 (dd, 2H), 4.11-4.17





(m, 3H), 7.14 (d, 2H), 7.76 (d, 2H)



278


1HNMR (CDCl3): 1.17 (s, 9H), 1.21-1.37 (m, 8H),






1.39-1.55 (m, 58H), 1.61-1.71 (m, 2H), 1.75-1.85





(m, 4H), 3.40-3.59 (m, 3H), 3.67-3.77 (m, 1H),





3.80-3.89 (m, 4H), 3.99 (dd, 2H), 4.69-4.72 (m,





1H), 6.84 (d, 2H), 7.43 (d, 2H)



279
hydro-

1HNMR (CD3OD): 1.36-1.43 (m, 8H), 1.55-1.65





chloride
(m, 4H), 1.75-1.94 (m, 4H), 3.29-3.34 (m, 4H),





3.44 (dd, 2H), 3.74 (dd, 2H), 3.95 (dd, 2H), 4.12-





4.19 (m, 3H), 7.15 (d, 2H), 7.76 (d, 2H)



280


1HNMR (CDCl3): 1.19-1.31 (m, 8H), 1.47-1.53






(m, 29H), 1.69-1.76 (m, 2H), 3.82-3.88 (m, 4H),





4.25 (dd, 2H), 4.35 (dd, 2H), 6.72 (d, 1H), 6.89 (d,





2H), 6.98 (d, 1H), 7.85 (d, 2H)









In the table, Boc or BOC indicates a t-butoxycarbonyl group. In the table, “-” means that a compound was synthesized as free form.










TABLE 95







Compound



No.
Structure





281


embedded image







282


embedded image







283


embedded image







284


embedded image







285


embedded image







286


embedded image







287


embedded image







288


embedded image







289


embedded image







290


embedded image
















Compound
Salt




No.
form
Physical property






281
hydro-

1HNMR (CD3OD): 1.34-1.39 (m, 8H), 1.54-1.61





chloride
(m, 2H), 1.70-1.79 (m, 2H), 3.15 (dd, 2H), 3.87 (dd,





2H), 4.35-4.42 (m, 4H), 6.98 (d, 1H), 7.06 (d, 1H),





7.14 (d, 2H), 7.81 (d, 2H)



282


1HNMR (CDCl3): 1.16 (s, 9H), 1.24-1.36 (m, 8H),






1.69-1.79 (m, 4H), 1.92 (dt, 2H), 2.24 (tt, 2H), 3.60





(dd, 2H), 3.70 (dd, 2H), 3.83 (dd, 2H), 3.95 (dd, 2H),





3.98 (dd, 2H), 4.12 (dd, 2H), 6.67-6.71 (m, 3H),





6.80 (d, 1H), 6.83 (d, 2H), 7.42 (d, 2H)



283
hydro-

1HNMR (CD3OD): 1.34-1.39 (m, 8H), 1.71-1.78





chloride
(m, 4H), 2.09 (dt, 2H), 2.27 (dt, 2H), 3.57 (dd, 4H),





3.85 (dd, 4H), 4.09-4.17 (m, 4H), 6.84 (d, 1H), 6.89





(d, 1H), 7.14 (d, 2H), 7.67 (d, 2H)



284


1HNMR (CDCl3): 1.17 (s, 9H), 1.20-1.37 (m, 8H),






1.42-1.55 (m, 54H), 1.60-1.68 (m, 4H), 3.38 (dd,





2H), 3.46-3.61 (m, 2H), 3.67-3.76 (m, 1H), 3.86





(dd, 2H), 3.96 (dd, 2H), 3.98-4.07 (m, 1H), 4.21 (dd,





2H), 4.71-4.80 (m, 1H), 6.85 (d, 2H), 7.45 (d, 2H)



285
hydro-

1HNMR (CD3OD): 1.36-1.44 (m, 8H), 1.54-1.66





chloride
(m, 4H), 3.14-3.24 (m, 4H), 3.67 (dd, 2H), 3.75 (dd,





2H), 3.96 (dd, 2H), 4.15 (dd, 1H), 4.24 (dd, 2H),





7.19 (d, 2H), 7.80 (d, 2H)



286
4-dodecyl-

1HNMR (CD3OD): 0.75-0.92 (m, 21H), 1.05-1.37





benzene
(m, 40H), 1.50-1.71 (m, 10H), 2.42-2.49 (m, 2H),




sulfonate
2.53-2.62 (m, 12H), 2.73 (dd, 2H), 3.12-3.21 (m,





4H), 3.68 (dd, 2H), 4.22 (dd, 2H), 7.16 (d, 2H), 7.22





(d, 6H), 7.75 (d, 6H), 7.81 (d, 1H)



287


1HNMR (CD3OD): 1.16 (s, 9H), 1.23-1.36 (m, 8H),






1.46-1.62 (m, 49H), 1.89-2.00 (m, 2H), 3.38 (dd,





2H), 3.50 (dd, 2H), 3.61 (dd, 2H), 3.73 (dd, 2H),





3.96 (dd, 2H), 4.27 (dd, 2H) 7.50-7.59 (m, 1H),





8.22 (d, 1H), 8.22-8.25 (m, 1H)



288
hydro-

1HNMR (CD3OD): 1.35-1.44 (m, 8H), 1.54-1.67





chloride
(m, 4H), 2.12 (dt, 2H), 3.16 (t, 2H), 3.21 (t, 2H),





3.63 (dd, 2H), 3.71 (dd, 2H), 4.32 (dd, 2H), 7.62





(dd, 1H), 8.05 (d, 1H), 8.49 (d, 1H)



289


1HNMR (CDCl3): 1.01 (s, 9H), 1.16-1.33 (m, 6H),






1.39-1.58 (m, 47H), 1.63-1.74 (m, 2H), 1.97 (tt,





2H), 3.46-3.55 (m, 2H), 3.67 (dd, 2H), 3.76 (dd,





2H), 3.85 (dd, 2H), 4.03-4.10 (m, 2H), 4.27-4.34





(m, 2H), 7.08-7.17 (m, 2H), 7.52-7.58 (m, 1H),





7.69 (dd, 2H), 7.87 (d, 1H)



290
hydro-

1HNMR (CD3OD): 1.34-1.44 (m, 6H), 1.55-1.67





chloride
(m, 4H), 2.15 (tt, 2H), 3.16 (dd, 2H), 3.22 (dd, 2H),





3.62-3.66 (m, 4H), 3.70-3.75 (m, 2H), 4.30 (dd,





2H), 7.32 (dd, 1H), 7.42 (d, 1H), 7.66 (dd, 1H), 8.00





(dd, 2H), 8.24 (d, 1H)









In the table, Boc or BOC indicates a t-butoxycarbonyl group. In the table, “-” means that a compound was synthesized as free form.










TABLE 96







Compound



No.
Structure





291


embedded image







292


embedded image







293


embedded image







294


embedded image







295


embedded image







296


embedded image







297


embedded image







298


embedded image







299


embedded image







300


embedded image
















Compound
Salt




No.
form
Physical property






291


1HNMR (CDCl3): 1.01 (s, 9H), 1.16-1.30 (m, 8H),






1.41-1.57 (m, 47H), 1.62-1.71 (m, 2H), 1.97 (tt,





2H), 3.37 (dd, 2H), 3.50 (dd, 2H), 3.67 (t, 2H), 3.76





(tt, 2H), 4.07 (dd, 2H), 4.30 (dd, 2H), 7.09-7.18 (m,





2H), 7.57 (dd, 1H), 7.69 (dd, 2H), 7.88 (d, 1H)



292
hydro-

1HNMR (CD3OD): 1.35-1.44 (m, 8H), 1.54-1.66





chloride
(m, 4H), 2.15 (tt, 2H), 3.15 (dd, 2H), 3.22 (dd, 2H),





3.63-3.66 (m, 4H), 3.71-3.74 (m, 2H), 4.29 (dd,





2H), 7.34 (dd, 1H), 7.42 (d, 1H), 7.69 (dd, 1H),





7.95-8.02 (m, 2H), 8.24 (d, 1H)



293


1HNMR (CDCl3): 1.14 (s, 9H), 1.19-1.27 (m, 8H),






1.43-1.57 (m, 42H), 1.60-1.69 (m, 2H), 1.91 (tt,





2H), 3.03-3.10 (m, 2H), 3.48 (dd, 2H), 3.59 (t, 2H),





3.68 (t, 2H), 3.96 (dd, 2H), 4.20 (dd, 2H), 6.87 (d,





2H), 7.40 (d, 2H)



294
hydro-

1HNMR (CD3OD): 1.36-1.44 (m, 8H), 1.58-1.70





chloride
(m, 4H), 2.09 (tt, 2H), 2.91 (dd, 2H), 3.21 (dd, 2H),





3.35-3.42 (m, 2H), 3.57 (dd, 4H), 3.68 (dd, 4H),





4.23 (dd, 2H), 7.18 (d, 2H), 7.68 (d, 2H)



295


1HNMR (CDCl3): 1.15 (s, 9H), 1.24-1.32 (m, 8H),






1.44-1.58 (m, 42H), 1.61-1.69 (m, 2H), 1.94 (tt,





2H), 2.15 (dd, 2H), 3.02-3.12 (m, 2H), 3.49 (dd,





2H), 3.59 (dd, 2H), 3.66-3.76 (m, 4H), 4.02 (dd,





2H), 6.85 (d, 2H), 7.40 (d, 2H)



296
hydro-

1HNMR (CD3OD): 1.36-1.44 (m, 8H), 1.58-1.74





chloride
(m, 4H), 2.09-2.16 (m, 4H), 2.90-2.96 (m, 2H),





3.17-3.21 (m, 2H), 3.34-3.40 (m, 4H), 3.41-3.51





(m, 2H), 3.54-3.62 (m, 4H), 4.13-4.21 (m, 2H),





7.14 (d, 2H), 7.64 (d, 2H)



297


1HNMR (CDCl3): 1.22-1.28 (m, 8H), 1.44-1.56






(m, 49H), 1.59-1.68 (m, 2H), 2.16 (tt, 2H), 3.04-





3.10 (m, 2H), 3.48 (dd, 2H), 3.69-3.78 (m, 4H),





4.06 (dd, 2H), 6.88 (d, 2H), 7.85 (d, 2H)



298
hydro-

1HNMR (CD3OD): 1.36-1.44 (m, 8H), 1.55-1.70





chloride
(m, 4H), 2.11 (tt, 2H), 2.91 (dd, 2H), 3.18 (dd, 2H),





3.29-3.38 (m, 4H), 3.43 (dd, 2H), 4.18 (dd, 2H),





7.18 (d, 2H), 7.80 (d, 2H)



299


1HNMR (CDCl3): 1.20-1.32 (m, 8H), 1.43-1.59






(m, 47H), 1.63-1.71 (m, 2H), 1.93 (tt, 2H), 2.74 (s,





3H), 3.25 (dd, 2H), 3.44-3.52 (m, 4H), 3.87 (dd,





2H), 3.96 (dd, 2H), 4.18 (dd, 2H), 6.85 (d, 2H), 7.30





(d, 2H)



300
hydro-

1HNMR (CD3OD): 1.35-1.44 (m, 8H), 1.53-1.65





chloride
(m, 4H), 2.18 (tt, 2H), 3.08 (s, 3H), 3.16 (dd, 2H),





3.21 (dd, 2H), 3.50 (dd, 2H), 3.62-3.69 (m, 4H),





4.21 (dd, 2H), 7.16 (d, 2H), 7.53 (d, 2H)









In the table, Boc or BOC indicates a t-butoxycarbonyl group. In the table, “-” means that a compound was synthesized as free form.










TABLE 97







Compound



No.
Structure





301


embedded image







302


embedded image







303


embedded image







304


embedded image







305


embedded image







306


embedded image







307


embedded image







308


embedded image







309


embedded image







310


embedded image
















Compound
Salt




No.
form
Physical property






301


1HNMR (CDCl3): 1.19 (s, 9H), 1.23-1.34 (m, 8H),






1.42-1.57 (m, 29H), 1.71-1.77 (m, 2H), 3.52-3.60





(m, 1H), 3.65-3.73 (m, 1H), 3.82-3.89 (m, 6H),





4.24 (dd, 2H), 4.32 (dd, 2H), 4.64-4.72 (m, 1H),





6.72 (d, 1H), 6.85 (d, 2H), 6.99 (d, 1H), 7.45 (d, 2H)



302
hydro-

1HNMR (CD3OD): 1.33-1.44 (m, 8H), 1.54-1.63





chloride
(m, 2H), 1.72-1.81 (m, 2H), 3.13-3.20 (m, 2H),





3.70-3.78 (m, 2H), 3.88 (dd, 2H), 3.92-3.98 (m,





2H), 4.14-4.19 (m, 1H), 4.34-4.42 (m, 4H), 6.98 (s,





1H), 7.06 (s, 1H), 7.17 (d, 2H), 7.79 (d, 2H)



303


1HNMR (CDCl3): 1.18 (s, 9H), 1.24-1.37 (m,






8H), 1.47-1.53 (m, 20H), 1.70-1.79 (m, 2H), 1.93





(dt, 2H), 3.61 (dd, 2H), 3.72 (dd, 2H), 3.83-3.91 (m,





4H), 4.28 (dd, 2H), 4.38 (dd, 2H), 6.75 (d, 1H), 6.97





(d, 1H), 7.23 (dd, 1H), 7.56 (d, 1H), 8.21 (d, 1H)



304
hydro-

1HNMR (CD3OD): 1.34-1.42 (m, 8H), 1.57 (dd,





chloride
2H), 1.71-1.80 (m, 2H), 2.11 (dd, 2H), 3.15 (dd,





2H), 3.58-3.65 (m, 4H), 3.88 (dd, 2H), 4.38-4.43





(m, 2H), 4.46-4.52 (m, 2H), 6.99 (s, 1H), 7.07 (s,





1H), 7.63 (d, 1H), 8.05 (d, 1H), 8.45 (s, 1H)



305


1HNMR (CDCl3): 1.12 (s, 9H), 1.19-1.36 (m, 8H),






1.43-1.56 (m, 47H), 1.64-1.71 (m, 2H), 3.38 (dd,





2H), 3.45-3.58 (m, 3H), 3.68-3.76 (m, 1H), 3.84-





3.92 (m, 2H), 3.94-4.00 (m, 2H), 4.12-4.26 (m,





2H), 4.29-4.39 (m, 1H), 4.54 (d, 1H), 4.67 (d, 1H),





6.86 (d, 2H), 7.30-7.37 (m, 5H), 7.46 (d, 2H)



306
hydro-

1HNMR (CD3OD): 1.35-1.42 (m, 8H), 1.54-1.65





chloride
(m, 4H), 3.16 (dd, 2H), 3.21 (dd, 2H), 3.60-3.78 (m,





5H), 4.19-4.31 (m, 4H), 4.63 (s, 2H), 7.18 (d, 2H),





7.29-7.38 (m, 5H), 7.69 (d, 2H)



307


1HNMR (CDCl3): 1.11 (s, 9H), 1.21-1.37 (m, 8H),






1.49 (s, 9H), 1.50-1.60 (m, 11H), 1.67-1.79 (m,





2H), 1.92 (dt, 2H), 2.06 (dt, 2H), 2.65 (t, 2H), 3.61





(t, 2H), 3.70 (t, 2H), 3.80-3.93 (m, 6H), 6.67 (d,





1H), 6.73 (d, 1H), 7.14 (d, 2H), 7.41 (d, 2H).



308
hydro-

1HNMR (CD3OD): 1.30-1.46 (m, 8H), 1.59 (dt,





chloride
2H), 1.75 (dt, 2H), 2.04-2.16 (m, 4H), 2.79 (t, 2H),





3.16 (t, 2H), 3.56-3.54 (m, 4H), 3.87 (t, 2H), 3.97





(t, 2H), 6.93-7.02 (m, 2H), 7.48 (d, 2H), 7.67 (d,





2H).



309


1HNMR (CDCl3): 1.10-1.25 (m, 8H), 1.43-1.67






(m, 31H), 1.76 (s, 3H), 2.27 (dt, 2H), 3.83 (t, 2H),





3.90-4.09 (m, 4H), 6.88 (d, 2H), 6.95 (s, 1H), 7.03





(s, 1H), 7.93 (d, 2H)



310
trifluoro-

13CNMR (D2O) 20.9 (CH3), 25.5 (CH2), 25.6





acetate
(CH2), 26.9 (CH2), 27.8 (CH2), 28.0 (CH2), 28.1





(CH2), 41.1 (CH2), 44.1 (CH2), 48.7 (CH2), 48.9





(CH2), 51.3 (CH2), 64.4 (CH2), 64.7 (CH2), 115,





119, 130, 138, 157, 163, 166, 173 (C═O)









In the table, Boc or BOC indicates a t-butoxycarbonyl group. In the table, “-” means that a compound was synthesized as free form.










TABLE 98







Compound



No.
Structure





311


embedded image







312


embedded image







313


embedded image







314


embedded image







315


embedded image







316


embedded image
















Compound
Salt




No.
form
Physical property






311


1HNMR (CDCl3): 1.16 (s, 9H), 1.22-1.32 (m, 8H),






1.36 (s, 9H), 1.44-1.60 (m, 38H), 1.61-1.69 (m,





2H), 1.94 (dt, 2H), 33.46 (t, 2H), 3.65 (t, 2H), 3.72





(t, 2H), 3.88 (t, 2H), 4.96 (s, 2H), 7.43 (dd, 1H),





7.75 (dd, 1H), 8.59 (d, 1H)



312
hydro-

1HNMR (CD3OD): 1.34-1.49 (m, 8H), 1.54-1.69





chloride
(m, 4H), 2.15 (t, 2H), 3.18 (t, 2H), 3.26 (t, 2H),





3.61-3.69 (m, 4H), 4.75 (s, 2H), 7.77 (d, 1H), 8.31





(d, 1H), 9.01 (m, 1H)



313


1HNMR (CDCl3): 1.13 (s, 9H), 1.33-1.39 (m,






17H), 1.48-1.59 (m, 38H), 1.69-1.79 (m, 2H), 1.95





(tt, 2H), 3.38 (dd, 2H), 3.54-3.69 (m, 4H), 3.73 (dd,





2H), 7.22 (d, 2H), 7.54 (s, 4H), 7.57 (d, 2H)



314
hydro-

1HNMR (CD3OD): 1.38-1.46 (m, 8H), 1.56-1.75





chloride
(m, 4H), 2.14 (tt, 2H), 3.17 (dd, 2H), 3.30-3.36 (m,





4H), 3.53 (dd, 2H), 7.43 (d, 2H), 7.84 (d, 2H), 7.86-





7.94 (m, 4H)



315


1HNMR (CDCl3): 1.16 (s, 9H), 1.24-1.36 (m, 8H),






1.47-1.54 (m, 20H), 1.59-1.72 (m, 2H), 1.94 (tt,





2H), 3.02-3.17 (m, 2H), 3.24 (dd, 2H), 3.42 (dd,





2H), 3.56-3.65 (m, 4H), 3.69 (dd, 2H), 3.88 (dd,





2H), 4.16 (dd, 2H), 6.89 (d, 2H), 7.41 (d, 2H)



316
hydro-

1HNMR (CD3OD): 1.33-1.44 (m, 8H), 1.54-1.67





chloride
(m, 4H), 2.10 (tt, 2H), 3.17 (dd, 2H), 3.34 (dd, 2H),





3.56-3.61 (m, 4H), 3.65-3.72 (m, 2H), 3.77-3.84





(m, 4H), 4.29 (dd, 2H), 7.15 (d, 2H), 7.69 (d, 2H)









In the table, Boc or BOC indicates a t-butoxycarbonyl group. In the table, “-” means that a compound was synthesized as free form.


SYNTHESIS EXAMPLE 1
Synthesis of tert-butyl 2-(4-hydroxyphenyl)-5,6-dihydro-4H-pyrimidine-1-carboxylate



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4-(1,4,5,6-tetrahydropyrimidin-2-yl)phenol (20 g) was dissolved in N, N-dimethylformamide (200 mL). Triethylamine (45.7 g) and di-tert-butyl dicarbonate (74 g) were added to the resultant under ice-cooling. The reaction mixture was warmed to room temperature and stirred at the same temperature overnight. Water was added to the reaction mixture, and the mixture was subjected to extraction with ethyl acetate. The resultant organic layer was dried over anhydrous sodium sulfate and filtered. Then, the filtrate was concentrated under reduced pressure. The resulting residue was dissolved in methanol (300 mL). 10% aqueous solution of sodium hydroxide (150 mL) was added to the solution at room temperature and the resultant was stirred at the same temperature for 6 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain the title compound (22.0 g, in a yield of 71%).



1H NMR (CDCl3): 1.14 (s, 9H), 1.93 (dt, 2H), 3.56 (dd, 2H), 3.70 (t, 2H), 6.58 (d, 2H), 7.23 (d, 2H).


SYNTHESIS EXAMPLE 2
(Step 1) Synthesis of tert-butyl 2-(4-iodophenyl)-5,6-dihydro-4H-pyrimidine-1-carboxylate



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A toluene solution of 2M trimethylaluminum (27 mL), 1,3-propanediamine (2.30 mL), and a toluene solution (10 mL) of ethyl 4-iodobenzoate (5.00 g) were added sequentially to toluene (145 mL) under a nitrogen atmosphere at room temperature, and the mixture was heated to 130° C. and stirred overnight. Then, the resultant was cooled to room temperature, followed by adding chloroform (36 mL), methanol (36 mL) and water (7.5 mL) sequentially thereto, and stirring the mixture at room temperature for 1 hour. Then, the reaction mixture was filtered with Celite (trademark) while washing with a mixture solvent composed of chloroform/methanol=9/1. The filtrate was concentrated under reduced pressure and the residue was dissolved in methanol. The resultant was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain a residue (5.77 g). Then, the residue was dissolved in N, N-dimethylformamide (91 mL). Di-tert-butyl dicarbonate (12.15 g) and triethylamine (6.76 g) were added to the solution, and stirred at room temperature overnight. The reaction mixture was poured into water, and the resultant was subjected to extraction with ethyl acetate. The resultant organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound (7.28 g, quantitative).



1H NMR (CDCl3): 1.15 (s, 9H), 1.92 (tt, 2H), 3.62 (t, 2H), 3.70 (t, 2H), 7.22 (d, 2H), 7.69 (d, 2H).


(Step 2) Synthesis of tert-butyl 2-[4-(3-hydroxyprop-1-ynyl)phenyl]-5,6-dihydro-4H-pyrimidine-1-carboxylate



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Tert-butyl 2-(4-iodophenyl) -5,6-dihydro-4H-pyrimidine-1-carboxylate (3.60 g) obtained in the step 1 was dissolved in triethylamine (10 mL), and propargyl alcohol (0.58 g), bis(triphenylphosphine)palladium (II) dichloride (65 mg) and copper iodide (I) (36 mg) were added to the solution, nitrogen purge was conducted, and the resultant was stirred at 80° C. for 40 minutes. Then, the resultant was cooled to room temperature, and poured into water to conduct extraction with ethyl acetate. The resultant organic layer was dried over anhydrous magnesium sulfate and filtered. Then, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound (1.94 g, in a yield of 66%).



1H NMR (CDCl3): 1.11 (s, 9H), 1.92 (tt, 2H), 3.63 (t, 2H), 3.70 (t, 2H), 4.49 (s, 2H), 7.36-7.50(m, 4H).


SYNTHESIS EXAMPLE 3
(Step 1) synthesis of [4-(1,4,5,6-tetrahydropyrimidin-2-yl)phenyl]methanol



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Ethyl 4-(hydroxymethyl) benzene-1-carboxyimidate hydrochloride salt (7.68 g) was dissolved in ethanol (36 mL). 1,3-propanediamine (2.64 g) was added to the solution and the mixture was heated under reflux overnight. Then, the resultant was cooled to room temperature and concentrated under reduced pressure. The precipitated solid was filtered while conducting washing with ethanol to obtain the title compound (2.78 g, in a yield of 41%).



1H NMR (CD3OD): 2.12 (tt, 2H), 3.60 (t, 4H), 4.71 (s, 2H), 7.58 (d, 2H), 7.68 (d, 2H).


(Step 2) Synthesis of tert-butyl 2-(4-(hydroxymethyl)phenyl)-5,6-dihydropyrimidine-1 (4H)-carboxylate



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[4-(1,4,5,6-tetrahydropyrimidin-2-yl)phenyl]methanol (4.52 g) obtained in the step 1 was dissolved in N, N-dimethylformamide (500 mL). At room temperature, triethylamine (16 mL) and N, N-dimethyl-4-aminopyridine (0.29 g) were added to the solution, and then di-tert-butyl dicarbonate (15.71 g) was added thereto. The reaction mixture was stirred at room temperature overnight and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound (4.57 g).



1H NMR (CD3OD): 1.10 (s, 9H), 1.94 (tt, 2H), 3.52 (t, 2H), 3.71 (t, 2H), 4.64 (s, 2H), 7.36-7.43 (m, 4H).


SYNTHESIS EXAMPLE 4
Synthesis of 4-[[3-[[tert-butyldimethylsilyl]oxy]propyl]thio]benzonitrile



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4-[3-[tert-butyl(dimethyl)silyl]oxypropylsulfanyl]benzonitrile (5.73 g) was dissolved in N, N-dimethylformamide (100 mL). At room temperature, imidazole (3.55 g) and tert-butyl dimethylchlorosilane (5.53 g) were added to the solution. The mixture was stirred for 1 hour, the resultant was poured into water, and the mixture was subjected to extraction with ethyl acetate. The resultant organic layer was washed with saturated saline solution, dried over anhydrous sodium sulfate, and then filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain the title compound (9.77 g).



1HNMR(CDCl3): 0.07 (s, 6H), 0.91 (s, 9H), 1.88 (t t, 2H), 3.08 (t, 2H), 3.73 (t, 2H), 7.32 (d, 2H), 7.52 (d, 2H).


SYNTHESIS EXAMPLE 5
Synthesis of tert-butyl 2-(6-(hydroxymethyl)pyridin-3-yl)-5,6-dihydropyrimidine-1(4H)-carboxylate



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1,3-diaminopropane (4.91 g) was dissolved in toluene (90 mL) under a nitrogen atmosphere. Trimethylaluminum (21 mL, 2.0M in a toluene solution) was added to the resultant while conducting cooling in an ice bath. The mixture was stirred for 1 hour at the same temperature, methyl 6-hydroxymethylpyridine-3-carboxylate (3.52 g) and toluene (100 mL) were added to the resultant at room temperature, and then the mixture was stirred at 80° C. overnight. Then, methanol was added to the resultant while conducting cooling in an ice bath and the mixture was filtered. The filtrate was concentrated under reduced pressure and the resulting residue was dissolved in N, N-dimethylformamide (200 mL). At room temperature, triethylamine (6 mL) was added to the solution, and then di-tert-butyl dicarbonate (7.09 g) and N,N-dimethyl-4-aminopyridine (0.29 g) were added thereto. At room temperature, the reaction mixture was stirred overnight and then filtered. The resultant was poured into water, and the mixture was subjected to extraction with ethyl acetate. The resultant organic layer was combined, dried over anhydrous sodium sulfate, and then filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography to obtain the title compound (0.86 g).



1H NMR (CDCl3): 1.16 (s, 9H), 1.95 (tt, 2H), 3.67 (t, 2H), 3.74 (t, 2H), 4.79 (s, 2H), 7.25 (d, 1H), 7.80 (dd, 1H), 8.63 (d, 1H).


SYNTHESIS EXAMPLE 6
Synthesis of tert-Butyl N-[4-[3-[[N,N′-bis(tert-butoxycarbonyl)carbamimidoyl]-methyl amino]propoxy]benzenecarboximidoyl]carbamate



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Tert-butyl N-[4-[3-(methylamino)propoxy]benzenecarboximidoyl]carbamate (254 mg) was dissolved in tetrahydrofuran (4 mL). Triethylamine (250 mg), silver trifluoromethanesulfonate (255 mg) and tert-butyl-N-[(tert-butoxycarbonylamino)-methylsulfanyl-methylene]carbamate (240 mg) were added to the solution under ice-cooling. The reaction mixture was warmed to room temperature and stirred at the same temperature overnight. The reaction mixture was filtered, and then the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound (301 mg, in a yield of 66%).



1H NMR (CDCl3): 1.46-1.59 (m, 27H), 2.14 (dt, 2H), 3.02 (s, 3H), 3.61-3.76 (m, 2H), 4.08 (t, 2H), 6.92 (d, 2H), 7.82 (d, 2H).


SYNTHESIS EXAMPLE 7
Synthesis of tert-Butyl N-[8-[[N,N′-bis(tert-butoxycarbonyl)carbamimidoyl]amino]octyl]-N-[N-tert-butoxycarbonyl-C-(4-hydroxy-1-piperidyl)carbonimidoyl]carbamate



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Tert-butyl (((tert-butoxycarbonyl)amino)(4-hydroxypiperidin-1-yl)methylene) carbamate (0.53 g) was dissolved in tetrahydrofuran (10 mL). Tert-butyl N-[(tert-butoxycarbonylamino)-(8-hydroxyoctylamino)methylene]carbamate (1.02 g) was added to the solution at room temperature. Triphenylphosphine (0.62 g) and bis(2-methoxyethyl)azodicarboxylate (0.58 g) were added to the mixture at room temperature. The resultant was stirred overnight, poured into water, and then subjected to extraction with ethyl acetate. The resultant organic layer was washed with saturated saline solution, dried over anhydrous sodium sulfate, and then filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography to obtain the title compound (0.64 g).



1H NMR (CDCl3): 1.20-1.38 (m, 8H), 1.40-2.00 (m, 44H), 3.15-4.33 (m, 9H).


SYNTHESIS EXAMPLE 8
Synthesis of tert-butyl 2-(8-hydroxyoctylamino)-4,5-dihydroimidazole-1-carboxylate



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2-(methylsulfanyl)-4,5-dihydro-1H-imidazole hydroiodide (4 g) was dissolved in methanol (50 mL). 1-amino-8-octanol (3.57 g) was added to the solution at room temperature. The reaction mixture was heated to 60° C., and stirred at the same temperature overnight. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was dissolved in N, N-dimethylformamide (50 mL), and triethylamine (9.96 g) and di-tert-butyl dicarbonate (12.52 g) were added thereto under ice-cooling. The reaction mixture was warmed to room temperature and stirred at the same temperature overnight. Water was added to the reaction mixture, and the mixture was subjected to extraction with ethyl acetate. The resultant organic layer was dried over anhydrous sodium sulfate, filtered, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound (1.86 g, in a yield of 36.2%).



1H NMR (CDCl3): 1.27-1.36 (m, 8H), 1.44-1.58 (m, 17H), 3.07-3.14 (m, 2H), 3.63 (dd, 2H).


SYNTHESIS EXAMPLE 9
(Step 1) Synthesis of tert-butyl 2-[4-[2-[2-(2,2,2-trifluoroacetyl)iminoimidazolidin-1-yl]ethoxy]phenyl]-5,6-dihydro-4H-pyrimidine-1-carboxylate



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Tert-butyl 2[4(2-bromoethoxy)phenyl]-5,6-dihydro-4H-pyrimidine-1-carboxylate (698 mg) was dissolved in N, N-dimethylformamide (8 mL). Potassium carbonate (344 mg) and 2,2,2-trifluoro-N-imidazolidin-2-ylidene-acetamide (300 mg) were added to the solution at room temperature. The reaction mixture was heated to 50° C. and stirred at the same temperature overnight. The reaction mixture was cooled to room temperature, water was added thereto, and the mixture was subjected to extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound (219 mg, in a yield of 27.3%).



1H NMR (CDCl3): 1.12 (s, 9H), 1.92 (tt, 2H), 3.60 (dd, 2H), 3.69 (dd, 2H), 3.73-3.82 (m, 4H), 3.82 (dd, 2H), 4.19 (dd, 2H), 6.85 (d, 2H), 7.43 (d, 2H)


(Step 2) Synthesis of tert-butyl 2-[4-[2-(2-iminoimidazolidin-1-yl)ethoxy]phenyl]-5,6-dihydro-4H-pyrimidine-1-carboxylate



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Tert-butyl 2-[4-[2-[2-(2,2,2-trifluoroacetyl)iminoimidazolidin-1-yl]ethoxy]phenyl]-5,6-dihydro-4H-pyrimidine-1-carboxylate (185 mg) obtained in the step 1 was dissolved in methanol (5 mL). Potassium carbonate (61 mg) was added to the solution at room temperature, and then the mixture was stirred at the same temperature overnight. The reaction mixture was concentrated under reduced pressure, water was added to the resulting residue, and then the mixture was subjected to extraction with ethyl acetate. The resultant organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain the title compound (140 mg, in a yield of 97.9%).



1H NMR (CD3OD): 1.13 (s, 9H), 1.92 (tt, 2H), 3.43-3.52 (m, 4H), 3.64-3.68 (m, 4H), 3.69 (dd, 2H), 4.19 (dd, 2H), 6.98 (d, 2H), 7.37 (d, 2H)


FORMULATION EXAMPLE (EMULSION)














Compound according to the present invention
5.62 parts by mass


Surfactant
4.49 parts by mass


Dimethylformamide
89.89 parts by mass 









The above components were mixed and dissolved to obtain each emulsion containing 5.62% of an active ingredient.


TEST EXAMPLE 1

(Apple Scab Control Test)


Each emulsion prepared in accordance with the formulation of the Formulation Example was diluted with water to contain 125 ppm of the active ingredient. The dilution was sprayed to apple seedlings (variety “Orin”, 3 to 4 leaf stage) grown in clay pots. The leaves were air-dried at room temperature. Then, the apple seedlings were inoculated with conidia of Apple scab fungus (Venturia inaequalis), and then held in a room at 20° C. under a high humidity with light and darkness being repeated every 12 hours. Control effects were examined by comparing lesion appearance state of the apple seedlings with that of untreated apple seedlings. The control value was calculated by the following equation.







Control





value






(
%
)


=

100
-



lesion





appearance





on





treated





apple





seedlings


lesion





appearance





on





untreated





apple





seedlings


×
100






Compounds represented by compound No. 2, 4, 6, 8, 10, 12, 16, 17, 20, 22, 25, 27, 29, 30, 32, 34, 36, 38, 40, 42, 44, 48, 50, 52, 57, 59, 61, 63, 65, 72, 73, 76, 78, 80, 82, 84, 86, 88, 89, 91, 93, 95, 97, 99, 101, 103, 105, 107, 109, 110, 112, 114, 116, 118, 120, 122, 124, 126, 128, 130, 132, 134, 136, 138, 140, 142, 143, 145, 147, 149, 151, 153, 155, 157, 159, 161, 163, 165, 167, 169, 171, 173, 175, 177, 179, 181, 184, 186, 188, 190, 192, 194, 196, 198, 200, 202, 206, 208, 210, 212, 214, 220, 222, 224, 226, 228, 230, 232, 234, 236, 238, 240, 242, 244, 246, 250, 254, 256, 262, 264, 266, 270, 271, 273, 275, 277, 279, 283, 285, 288, 290, 292, 294, 296, 298, 300, and 302 were subjected to the apple scab control test. All of the compounds showed at least 75% control value.


TEST EXAMPLE 2

(Cucumber Gray Mold Control Test)


Each emulstion prepared in accordance with the formulation of the Formulation Example was diluted with water to contain 125 ppm of the active ingredient. The dilution was sprayed to cucumber seedlings (variety “Cucumis sativus”, cotyledon stage) grown in clay pots. The leaves were air-dried at room temperature. Then, a conidia suspension of cucumber gray mold fungus (Botrytis cinerea) was dropped on the cucumber seedlings to inoculate the cucumber seedlings therewith, and then the cucumber seedlings were held in a dark room at 20° C. under a high humidity for 4 days. Control effects were examined by comparing lesion appearance state on leaves of the cucumber seedlings with that of untreated cucumber seedlings in the same manner as Example 1.


Compounds represented by compound No. 2, 4, 6, 8, 10, 12, 14, 16, 17, 20, 22, 25, 27, 29, 30, 32, 34, 36, 38, 40, 42, 44, 46, 48, 50, 52, 54, 57, 59, 61, 63, 65, 72, 76, 78, 80, 82, 84, 86, 88, 89, 91, 93, 95, 99, 101, 103, 105, 107, 109, 110, 112, 114, 116, 118, 120, 122, 124, 126, 128, 130, 132, 134, 136, 138, 140, 142, 143, 145, 147, 149, 151, 153, 155, 157, 159, 161, 163, 165, 167, 169, 171, 173, 175, 177, 179, 181, 184, 186, 188, 190, 192, 194, 196, 198, 200, 202, 204, 206, 208, 210, 212, 214, 216, 218, 220, 222, 224, 226, 228, 230, 232, 234, 236, 238, 240, 242, 244, 246, 248, 250, 252, 254, 256, 258, 260, 262, 264, 266, 268, 273, 275, 277, 279, 281, 283, 285, 286, 288, 296, 298, 300, and 302 were subjected to the cucumber gray mold control test. All of the compounds showed at least 75% control value.


TEST EXAMPLE 3

(Wheat Powdery Mildew Control Test)


Each emulstion prepared in accordance with the formulation of the Formulation Example was diluted with water to contain 125 ppm of the active ingredient. The dilution was sprayed to wheat seedlings (variety “Chihoku”, 1.0 to 1.2 leaf stage) grown in clay pots. The leaves were air-dried at room temperature. Then, conidia of wheat powdery mildew fungus (Blumeria graminis f. sp. tritici) was sprinkled on the wheat seedlings to inoculate the wheat seedlings therewith, and then the wheat seedlings were held in a greenhouse at 22 to 25° C. for 7 days. Control effects were examined by comparing lesion appearance state on the wheat leaves with that of untreated wheat leaves in the same manner as Example 1.


Compounds represented by compound No. 2, 6, 8, 10, 12, 16, 17, 20, 22, 25, 29, 30, 32, 34, 36, 40, 42, 44, 46, 50, 52, 57, 59, 61, 63, 65, 72, 82, 89, 93, 99, 101, 103, 105, 107, 109, 110, 112, 114, 120, 122, 126, 128, 130, 132, 134, 136, 138, 140, 142, 143, 145, 147, 149, 151, 153, 155, 157, 159, 161, 163, 165, 167, 169, 171, 173, 175, 177, 179, 181, 184, 186, 188, 190, 192, 194, 196, 198, 200, 202, 204, 206, 208, 210, 212, 214, 216, 218, 220, 222, 224, 228, 230, 232, 234, 236, 238, 240, 242, 246, 248, 250, 252, 254, 256, 258, 260, 262, 264, 266, 268, 270, 271, 273, 275, 277, 279, 281, 283, 285, 286, 288, and 300 were subjected to the wheat powdery mildew control test. All of the compounds showed at least 75% control value.


TEST EXAMPLE 4

(Tomato Late Blight Control Test)


Each emulstion prepared in accordance with the formulation of the Formulation Example was diluted with water to contain 125 ppm of the active ingredient. The dilution was sprayed to tomato seedlings (variety “Regina”, 4 to 5 leaf stage) grown in clay pots. The leaves were air-dried, and a zoosporangia suspension of Tomato late blight fungus (Phytophthora infestans) was sprayed on the tomato seedlings to inoculate the tomato seedlings therewith, and then the tomato seedlings were held in a thermostatic chamber (20° C.) under a high humidity with light and darkness being repeated every 12 hours for 4 days. The lesion appearance state on the leaves was compared with that of untreated leaves in the same manner as Example 1 to obtain the control value.


Compounds represented by compound No. 2, 6, 8, 10, 16, 20, 22, 25, 27, 29, 30, 32, 34, 36, 40, 42, 44, 52, 54, 57, 61, 76, 80, 82, 84, 86, 88, 89, 91, 93, 99, 101, 103, 105, 107, 109, 110, 112, 114, 116, 118, 120, 122, 124, 126, 128, 130, 132, 134, 136, 138, 140, 142, 143, 145, 147, 149, 151, 153, 155, 157, 159, 163, 165, 167, 169, 171, 173, 177, 179, 181, 184, 186, 188, 190, 192, 194, 196, 198, 200, 202, 204, 206, 208, 210, 212, 214, 216, 218, 220, 222, 224, 228, 230, 232, 234, 240, 242, 246, 248, 250, 252, 254, 256, 258, 260, 264, 266, 268, 270, 271, 273, 275, 277, 279, 281, 285, 288, 290, 292, 298, 300, and 302 were subjected to the tomato late blight control test. All of the compounds showed at least 75% control value.


TEST EXAMPLE 5

(Wheat Leaf Rust Control Test)


Each emulstion prepared in accordance with the formulation of the Formulation Example was diluted with water to contain 125 ppm of the active ingredient. The dilution was sprayed to wheat seedlings (variety “Norin 61”, 1.0 to 1.2 leaf stage) grown in clay pots. The leaves were air-dried, uredospores of wheat leaf rust fungus (Puccinia recondita) were sprinkled thereon to inoculate the leaves therewith, and then the wheat seedlings were held in a greenhouse at 22 to 25° C. for 10 days. The lesion appearance state on the leaves was compared with that of untreated leaves in the same manner as Example 1 to obtain the control value.


Compounds represented by compound No. 6, 8, 10, 16, 20, 22, 25, 29, 32, 34, 40, 42, 48, 50, 52, 57, 59, 61, 72, 89, 103, 107, 109, 110, 112, 114, 120, 122, 124, 126, 128, 130, 136, 140, 142, 143, 145, 151, 153, 157, 163, 165, 167, 169, 171, 173, 177, 179, 184, 186, 188, 192, 194, 200, 204, 206, 216, 218, 220, 222, 228, 230, 232, 234, 236, 238, 240, 242, 244, 246, 248, 252, 254, 256, 258, 260, 262, 264, 266, 268, 270, 271, 273, 275, 277, 279, 281, 285, 286, 288, 292, 298, 300, and 302 were subjected to the wheat leaf rust control test. All of the compounds showed at least 75% control value.


INDUSTRIAL APPLICABILITY

The guanidine compound (the compound of formula [I] or the salt thereof) according to the present invention has excellent fungicidal activity, is safe to use, and can be industrially advantageously synthesized. The fungicide or the plant disease-controlling agent containing the guanidine compound as an active ingredient thereof is particularly excellent in controlling plant diseases such as apple scab, cucumber gray mold, wheat powdery mildew, tomato late blight, and wheat leaf rust.

Claims
  • 1. A compound of formula [I]:
  • 2. A fungicide comprising, as an active ingredient thereof, at least one selected from a compound of formula [I]:
  • 3. A plant disease-controlling agent comprising, as an active ingredient thereof, at least one selected from a compound of formula [I]:
Priority Claims (1)
Number Date Country Kind
2015-113376 Jun 2015 JP national
PCT Information
Filing Document Filing Date Country Kind
PCT/JP2016/066603 6/3/2016 WO 00
Publishing Document Publishing Date Country Kind
WO2016/195077 12/8/2016 WO A
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Entry
J.ordan, V. C. Nature Reviews: Drug Discovery, 2, 2003, 205.
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Related Publications (1)
Number Date Country
20180146677 A1 May 2018 US