TREA

1,3,4-thiadiazoles useful for the treatment of CMV infections

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Information

  • Patent Grant
  • 6150385
  • Patent Number
    6,150,385
  • Date Filed
    Tuesday, March 16, 1999
    25 years ago
  • Date Issued
    Tuesday, November 21, 2000
    24 years ago
Information
Abstract
The present invention presents novel 1,3,4-thiadiazole derivatives of formula I ##STR1## which have useful antiviral activity against herpes virus, cytomegalovirus (CMV).
Description

BACKGROUND OF THE INVENTION
The present invention relates to novel 1,3,4-thiadiazole derivatives having useful antiviral activity against herpes virus, cytomegalovirus (CMV). The invention also relates to a pharmaceutical composition containing such compounds and methods for the treatment of such viral infections. Many of these compounds are also active against other herpes viruses, such as the varicella zoster virus, the Epstein-Barr virus, the herpes simplex virus, and the human herpes virus type 8 (HHV-8).
INFORMATION DISCLOSURE
Derwent Abstracts 07484C/05 discloses 2-acylamino-1,3,4-thiadiazole derivatives useful as pesticides, optical brightening agents, and intermediates for pharmaceuticals.
Derwent Abstracts 46012X/24 discloses anti-inflammatory composition containing 1,3,4-thiadiazoles derivatives as active agents.
J. Chem. Soc. (C), Vol. 13, 1813-1823, (1970) describes addition-cyclisation reactions undergone by aroyl isothiocyanates with NN'-diaminoguanidines.
J. Heterocyclic Chem. Vol. 25, 1071-1074 describes a new route to 1,2,4-triazoles and 1,3,4-thiadiazoles from 1-acylbithiourea.
SUMMARY OF THE INVENTION
The present invention provides a compound of formula I ##STR2## or pharmaceutically acceptable salts thereof wherein: Y is
a) --NHR.sub.1, or ##STR3## X is --O--, --S(.dbd.O).sub.h --, --CH.sub.2 --, or --NR.sub.2 --; R.sub.1 is
a) C.sub.1-18 alkyl,
b) --(CH.sub.2).sub.i --C.sub.3-7 cycloalkyl,
c) --(CH.sub.2).sub.i -bicycloalkyl,
d) --(CH.sub.2).sub.j -M,
e) --(CH.sub.2).sub.j -W,
f) --(CH.sub.2).sub.k aryl, wherein aryl may be substituted with one to three R.sub.3,
g) --(CH.sub.2).sub.k -het, wherein het may be substituted with one to three R.sub.3,
h) --(CH.sub.2).sub.k -Q, wherein Q may be substituted with one to three R.sub.3, or
i) H;
R.sub.2 is
a) H,
b) C.sub.1-4 alkyl,
c) --C(.dbd.O)C.sub.1-4 alkyl,
d) --S(.dbd.O)C.sub.1-4 alkyl,
e) --CO.sub.2 C.sub.1-4 alkyl, or
f) --CO.sub.2 CH.sub.2 phenyl;
R.sub.3 is
a) halo,
b) C.sub.1-4 alkyl,
c) C.sub.1-4 alkoxy,
d) benzyl,
e) --CN,
f) --SO.sub.2 F,
g) --SO.sub.2 NH.sub.2,
h) --CF.sub.3,
i) --NO.sub.2,
j) --OCH.sub.2 O--,
k) --CO.sub.2 (C.sub.1-4 alkyl),
l) --C(.dbd.O)C.sub.l-4 alkyl,
m) --C(.dbd.O)NH.sub.2,
n) --NHCO.sub.2 (C.sub.1-4 alkyl), or
o) --C(.dbd.O)--O--C(.dbd.O)--;
M is
a) --CN
b) halo,
c) --CO.sub.2 C.sub.1-4 alkyl,
d) --CH(phenyl).sub.2, ##STR4## W is a) --OR.sub.4,
b) --SR.sub.4,
c) --NHR.sub.5, or
d) --NR.sub.6 R.sub.7 ;
R.sub.4 is
a) C.sub.1-4 alkyl,
b) C.sub.3-7 cycloalkyl, or
c) aryl,
R.sub.5 is
a) C.sub.1-7 alkyl,
b) C.sub.3-7 cycloalkyl,
c) aryl, or
d) --C(.dbd.O)C.sub.1-4 alkyl;
R.sub.6 and R.sub.7 are independently
a) C.sub.1-4 alkyl, or
b) R.sub.6 and R.sub.7 together with nitrogen form a 4- to 6-membered saturated heterocyclic moiety having one to two atoms selected from the group consisting of oxygen, nitrogen, and sulfur;
R.sub.x is
a) C.sub.1-18 alkyl,
b) C.sub.2-18 alkenyl,
c) C.sub.2-18 alkynyl,
d) C.sub.2-6 alkyl substituted with one to three halo, C.sub.1-3 alkoxy, --OH, --SH, or --CO.sub.2 H,
e) C.sub.2-6 alkenyl substituted with aryl, wherein the aryl may be in turn substituted with one to three R.sub.2,
f) --(CH.sub.2).sub.i aryl, wherein aryl may be substituted with one to three R.sub.3,
g) --(CH.sub.2).sub.i -Q, wherein Q may be substituted with one to three R.sub.3, or
h) --(CH.sub.2).sub.i -U, wherein U may be substituted with one to three R.sub.3 ;
aryl is phenyl or naphthyl;
het is 5- to 10-membered unsaturated heterocyclic moiety having one to three atoms selected from the group consisting of oxygen, nitrogen, and sulfur;
U is 5- to 9-membered unsaturated heterocyclic moiety having one to three atoms selected from the group consisting of oxygen, nitrogen, and sulfur;
Q is 5- or 6-membered saturated heterocyclic moiety having one to two atoms selected from the group consisting of oxygen, nitrogen, and sulfur, wherein nitrogen atom may be in turn substituted with C.sub.1-4 alkyl, phenyl, benzyl, --C(.dbd.O)C.sub.1-4 alkyl, or --CO.sub.2 C.sub.1-4 alkyl;
h is 0, 1, or 2; i is 0, 1, 2, 3, or 4; j is 2, 3, or 4; k is 0, 1, 2, 3, 4, 5, or 6;
and with the following provisos:
a) where R.sub.3 is phenyl or 4-methoxyphenyl, R.sub.1 is other than phenyl, 4-methoxyphenyl, or 4-chlorophenyl;
b) where R.sub.3 is --CH.sub.2 phenyl, R.sub.1 is other than phenyl or --CH.sub.2 phenyl;
c) where R.sub.3 is H, substituted or unsubstituted alkyl or phenyl, R.sub.1 is other than unsubstituted alkyl or phenyl.
The compounds of the present invention have antiviral activity against cytomegalovirus (CMV), a member of herpes virus.
DETAILED DESCRIPTION OF THE INVENTION
For the purpose of the present invention, the carbon content of various hydrocarbon containing moieties is indicated by a prefix designating the minimum and maximum number of carbon atoms in the moiety, i.e., the prefix C.sub.i-j defines the number of carbon atoms present from the integer "i" to the integer "j", inclusive. Thus, C.sub.1-4 alkyl refers to alkyl of one to four carbon atoms, inclusive, or methyl, ethyl, propyl, butyl, and isomeric forms such as, for example, straight and branched form thereof.
The terms "C.sub.1-4 alkyl", and "C.sub.1-18 alkyl" refer to an alkyl group having one to four, or one to eighteen carbon atoms respectively such as, for example, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl and their isomeric forms thereof.
The terms "C.sub.2-18 alkenyl" refers to at least one double bond alkenyl group having two to eighteen carbon atoms, for example, ethenyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, heptenyl, octenyl, octadienyl, octatrienyl, nonenyl, undecenyl, dodecenyl, etc., and their isomeric forms thereof.
The term "C.sub.2-18 alkynyl" refers to at least one triple bond alkynyl group having two to twelve carbon atoms such as, for example, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl, octynyl, octadiynyl, octatriynyl, nonynyl, nonediynyl, etc., and their isomeric forms thereof.
The term "C.sub.3-7 cycloalkyl" refers to monocyclic hydrocarbons having three to seven carbon atoms such as, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and their isomeric forms thereof, preferably an cycloalkyl group having three to six carbon atoms.
The term "bicycloalkyl" refers to saturated alicyclic hydrocarbon systems consisting of two rings only, having two or more atoms in common.
The terms "C.sub.1-4 alkoxy" refers to an alkyl group having one to four carbon atoms attached to an oxygen atom of hydroxyl group such as; for example, methoxy, ethoxy, propyloxy, butyloxy, and their isomeric forms thereof.
The term "aryl" refers to monocarbocyclic or bicarbocyclic aromatic moiety such as; for example phenyl, naphthyl, biphenyl. Each of these moieties may be substituted as appropriate. Aryl is preferably phenyl or phenyl substituted with C.sub.1-4 alkyl, C.sub.1-4 alkoxy, halo, --CN, --SO.sub.2 NH.sub.2, --SO.sub.2 F--, --NO.sub.2, --C(.dbd.O)--O--C(.dbd.O)-- or --OCH.sub.2 O--.
The term "het" refers to a 5- to 10-membered unsaturated heterocyclic moiety having one to three atoms selected from the group consisting of oxygen, nitrogen, and sulfur such as, for example, furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, pyranyl, indazolyl, benzothiazolyl, benzoimidazolyl, benzofuryl, isobenzofuryl, benzothiazole, benzoisoxazole, benzothienyl, indolyl, isoindolyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, phthalazinyl or cinnolinyl.
The term "U" refers to 5- to 9-membered unsaturated heterocyclic moiety having one to three atoms selected from the group consisting of oxygen, nitrogen, and sulfur such as, for example, furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, pyranyl, indazolyl, benzothiazolyl, benzoimidazolyl, benzofuryl, isobenzofuryl, benzothiazole, benzoisoxazole, benzothienyl, indolyl, or isoindolyl.
The term "Q" refers to 5- or 6-membered saturated heterocyclic moiety having one to two atoms selected from the group consisting of oxygen, nitrogen, and sulfur, wherein nitrogen atom may be in turn substituted with C.sub.1-4 alkyl, phenyl, benzyl, or --C(.dbd.O)C.sub.1-4 alkyl. The example of Q is 2-, 3-, or 4-piperidinyl, 1-, or 2-pyrrolidinyl, morpholinyl, thiomorpholinyl, dioxolanyl, imidazolidinyl, oxathiolanyl, oxazolidinyl, tetrahydrofuryl, or 2-oxo-1-pyrrolidinyl.
The term "halo" refers to fluoro, chloro, bromo, or iodo.
The term "pharmaceutically acceptable salts" refers to those salts which possess the biological effectiveness and properties of the parent compound and which are not biologically or otherwise undesirable.
Throughout this application, abbreviations which are well known to one of ordinary skill in the art may be used, such as "Ph" for phenyl, "Me" for methyl, etc.
Examples of preferred compounds of the present invention are:
1. N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-2-ethoxy-1-naphthamide,
2. N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide,
3. N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide,
4. N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide,
5. 1,3-dioxo-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]-1,3-dihydro-2-benzofuran-5-carboxamide,
6. N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)-1,3,4-thiadiazol-2-yl]-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide,
7. 1,3-dioxo-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dihydro-2-benzofuran-5-carboxamide,
8. N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide,
9. (E)-N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-9-octadecenamide,
10. 2-ethoxy-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-1-naphthamide,
11. 2,6-dichloro-N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)benzamide,
12. N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-2-ethoxy-1-naphthamide,
13. N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)-1,3,4-thiadiazol-2-yl]-2-ethoxy-1-naphthamide,
14. (E)-N-(5-{[4-(aminosulfonyl)benzyl]aminol-1,3,4-thiadiazol-2-yl)-9-octadecenamide,
15. N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}-2-ethoxy-1-naphthamide,
16. (E)-N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-3-phenyl-2-propenamide,
17. 2,6-dichloro-N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
18. 2,6-dichloro-N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
19. (E)-N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4-thiadiazol-2-yl}-9-octadecenamide,
20. N-(5-{[4-(aminosulfonyl)benzyl]amino}-1,3,4-thiadiazol-2-yl)-2,6-dichlorobenzamide,
21. 2,6-dichloro-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2yl)benzamide,
22. 4-cyano-N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
23. N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide,
24. 4-cyano-N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2yl)benzamide,
25. N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-5-nitro-2-furamide,
26. 2,6-dichloro-N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)-1,3,4-thiadiazol-2-yl]benzamide,
27. 4-cyano-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)benzamide,
28. N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide,
29. N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2,6-dichlorobenzamide,
30. N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}-2-methoxybenzamide,
31. (E)-N-(5-{[4-(aminosulfonyl)benzyl]amino}-1,3,4-thiadiazol-2-yl)-3-phenyl-2-propenamide,
32. (E)-N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)-1,3,4-thiadiazol-2-yl]-9-octadecenamide,
33. (E)-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-9-octadecenamide,
34. (E)-N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-9-octadecenamide,
35. (E)-N-{5-[(4-fluorobenzyl)amino]-1,3,4-thiadiazol-2-yl}-9-octadecenamide,
36. 2,6-dichloro-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, or
37. N-(5-{[4-(aminosulfonyl)benzyl]amino-1,3,4-thiadiazol-2-yl)-2-ethoxy-1-naphthamide.
Examples of more preferred compounds of the present invention are:
1. N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-2-ethoxy-1-naphthamide,
2. N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide,
3. N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide,
4. N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide,
5. 1,3-dioxo-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]-1,3-dihydro-2-benzofuran-5-carboxamide,
6. N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)-1,3,4-thiadiazol-2-yl]-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide,
7. 1,3-dioxo-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dihydro-2-benzofuran-5-carboxamide,
8. N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide, or
9. (E)-N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-9-octadecenamide.
The compounds of the present invention and pharmaceutically acceptable salts thereof are useful as antiviral agents. Thus, these compounds are useful to combat viral infections in animals, including man. Specifically, these compounds have anti-viral activity against the herpes virus, cytomegalovirus (CMV). Many of these compounds are also active against other herpes viruses, such as the varicella zoster virus, the Epstein-Barr virus, the herpes simplex virus, and the human herpes virus type 8 (HHV-8).
Also, while many of the compounds of the present invention have shown activity against the CMV polymerase, these compounds may be active against the cytomegalovirus by this or other mechanisms of action. Thus, the description below of these compounds' activity against the CMV polymerase is not meant to limit the present invention to a specific mechanism of action.
The compounds of the present invention are tested in an polymerase assay to show activity described below, which is indicative of a compound's activity and thus of its use as an anti-viral agent.
The HCMV polymerase assay is performed using a scintillation proximity assay (SPA) as described in several references, such as N. D. Cook, et al., Pharmaceutical Manufacturing International, pages 49-53 (1992); K. Takeuchi, Laboratory Practice, September issue (1992); U.S. Pat. No. 4,568,649 (1986); which are incorporated by reference herein. Reactions are performed in 96-well plates. The assay is conducted in 100 .mu.l volume with 5.4 mM HEPES (pH 7.5), 11.7 mM KCl, 4.5 mM MgCl.sub.2, 0.36 mg/ml BSA, and 90 nM .sup.3 H-dTTP. Assays are run with and without CHAPS, (3-[(3-Cholamidopropyl)-dimethylammonio]-1-propanesulfonate) at a final concentration of 2 mM. HCMV is diluted in enzyme dilution buffer containing 50% glycerol, 250 mM NaCl, 10 mM HEPES (pH 7.5), 100 .mu.g/ml BSA, and 0.01% sodium azide. The HCMV polymerase, which is expressed in recombinant baculovirus-infected SF-9 cells and purified according to literature procedures, is added at 10% (or 10 .mu.l) of the final reaction volume, i.e., 100 .mu.l. Compounds are diluted in 50% DMSO and 10 .mu.l are added to each well. Control wells contain an equivalent concentration of DMSO. Unless noted otherwise, reactions are initiated via the addition of 6 nM biotinylated poly(dA)-oligo(dT) template/primer to reaction mixtures containing the enzyme, substrate, and compounds of interest. Plates are incubated in a 25.degree. C. or 37.degree. C. H.sub.2 O bath and terminated via the addition of 40 .mu.l/reaction of 0.5 M EDTA (pH 8) per well. Reactions are terminated within the time-frame during which substrate incorporation is linear and varied depending upon the enzyme and conditions used, i.e., 30 min. for HCMV polymerase. Ten .mu.l of streptavidin-SPA beads (20 mg/ml in PBS/10% glycerol) are added following termination of the reaction. Plates are incubated 10 min. at 37.degree. C., then equilibrated to room temperature, and counted on a Packard Topcount. Results of the testing of compounds of the present invention in this assay are shown in TABLE 1 below.
These compounds of the present invention are administered in a pharmaceutical composition containing the compound in combination with a suitable excipient, the composition being useful in combating viral infections. Pharmaceutical compositions containing a compound appropriate for antiviral use are prepared by methods and contain excipients which are well known in the art. A generally recognized compendium of such methods and ingredients is Remington's Pharmaceutical Sciences by E. W. Martin (Mark Publ. Co., 15th Ed., 1975), which is hereby incorporated by reference herein.
The quantity of active component, that is the compounds of formula I according to this invention, in the pharmaceutical composition and unit dosage form thereof may be varied or adjusted widely depending upon the particular application method, the potency of the particular compound and the desired concentration. Generally, the quantity of active component will range between 0.5% to 90% by weight of the composition.
The compounds of the present invention are administered parenterally (for example, by intravenous, intraperitoneal or intramuscular injection), topically, orally, or rectally, depending on whether the preparation is used to treat internal or external viral infections.
For internal infections, the compositions are administered orally or parenterally at dose levels, calculated as the free base, of about 0.1 to 300 mg/kg, preferably 1.0 to 30 mg/kg of mammal body weight, and are used in man in a unit dosage form, administered one to four times daily in the amount of 1 to 1000 mg per unit dose.
For parenteral administration or for administration as drops, as for eye infections, the compounds are presented in aqueous solution in a concentration of from about 0.1 to 10%, more preferably about 0.1 to 7%. The solution may contain other ingredients, such as emulsifiers, antioxidants or buffers.
The exact regimen for administration of the compounds and compositions disclosed herein will necessarily be dependent upon the needs of the individual subject being treated, the type of treatment and, of course, the judgment of the attending practitioner.
The following Scheme outlines the preparation of the compounds of the present invention. ##STR5##
In Scheme I, Y is --NHR.sub.1, or ##STR6## R.sub.1 Rx and X are as defined previously. The synthesis of structures 3 and 4, the compounds of the present invention, required two or three steps. 2-Amino-5-bromo-1,3,4-thiadiazole 2 is prepared through bromination of commercially available 2-amino-1,3,4-thiadiazole. Compound 3 is prepared through direct bromide displacement of thiadiazole 2 with an appropriate amine. Compound 3 then react with an appropriate acid chloride to provide compound 4.
It will be apparent to those skilled in the art that the described synthetic procedures are merely representative in nature and that alternative synthetic processes are known to one of ordinary skill in organic chemistry.





The compounds and their preparations of the present invention will be better understood in connection with the following examples, which are intended as an illustration of and not a limitation upon the scope of the invention.
EXAMPLE 1
Preparation of Starting Material 5-bromo-1,3,4-thiadiazol-2ylamine.
To a stirred solution of 2-amino-1,3,4-thiadiazole (40.5 g) in 250 ml of acetic acid is added 22.7 ml of bromine over about 20 minutes. The flask is surrounded by an ice bath during the addition to maintain the reaction temperature near 25.degree. C. Following the addition, the ice bath is removed and the clear red solution stirred at ambient temperature for 18 hours, then added to 1L of cracked ice. Excess bromine is quenched with NaHSO.sub.3, and 40 ml of 50% aqueous NaOH is added. The precipitated solid is isolated by filtration and washed well with water, then dissolved in 300 ml of water containing 40 ml concentrated. HCl. The solution is filtered from a small amount of solid, then 87 g of K.sub.2 HPO.sub.4 in a small quantity of water is added. The resulting slurry is chilled in ice and filtered, and the solid washed well with water. Recrystallization of the product from 400 ml of ethanol provides 26.3 g of the title compound.
.sup.1 NMR (DMSO-d.sub.6) .delta. 7.51 ppm.
EXAMPLE 2
Preparation of tert-Butyl 4-(5-amino-1,3,4-thiadiazol-2-yl)tetrahydro-1(2H)-pyrazinecarboxylate. ##STR7##
A mixture of 5-bromo-1,3,4-thiadiazol-2-ylamine (9.27 g), Boc-piperazine (11.51 g), and K.sub.2 HPO.sub.4 (13.4 g) in 30 ml of DMF is heated at 100.degree. C. under argon for four hours, then cooled and added to 100 g of ice. The mixture is extracted with ethyl acetate, and the organic phase washed twice with water and dried (MgSO.sub.4). Following removal of the solvent under reduced pressure, the residue is flash chromatographed on silica using 4% methanol in dichloromethane to afford 8.32 g of the title compound as a solid. Recrystallization from 240 ml of 1:1 acetonitrile-toluene provides 6.65 g of solid.
.sup.1 NMR .delta. 1.47, 3.34, 3.53, 4.8 ppm; IR 3411, 3132, 1698, 1676, 1500, 1427, 1251, 1167 cm.sup.-1 ; EI HRMS m/z found: 285.1277; M.p. 215-216.degree. C.
EXAMPLE 3
Preparation of N-(5-Amino-1,3,4-thiadiazol-2-yl)-N-phenethylamine. ##STR8##
A mixture of 5-bromo-1,3,4-thiadiazol-2-ylamine (360 mg), phenethylamine (0.38 ml), and K.sub.2 HPO.sub.4 (522 mg) in 2 ml of DMF is heated under nitrogen at 100.degree. C. for two hours, then partitioned between water and ethyl acetate. The organic phase is washed with water and brine, dried over MgSO.sub.4, and concentrated under reduced pressure. Flash chromatography of the residue on silica using 4-5% methanol in dichloromethane provides 261 mg of the title compound. Recrystallization of 238 mg of this from 10 ml of 1:1 acetonitrile toluene affords 205 mg of crystals.
.sup.1 H NMR .delta. 2.92, 3.50, 7.2-7.3 ppm; IR 3186, 1565, 1505 cm.sup.-1 ; EI MS m/z 221; M.p. 156-157.degree. C.; Anal. Found: C, 54.51; H, 5.47; N, 25.26; S, 14.30.
EXAMPLE 4
Preparation of 5-Morpholino-1,3,4-thiadiazol-2-ylamine. ##STR9##
A mixture of 5-bromo-1,3,4-thiadiazol-2-ylamine, K.sub.2 HPO.sub.4 (5.7 g), and 5.3 ml of morpholine in 20 ml of DMF is heated at 80.degree. C. under nitrogen for 18 hours, then diluted with 50 ml of water. The clear solution is placed in a continuous extractor and extracted with a brisk flow of dichloromethane for 18 hours. The solution is dried over MgSO.sub.4 and concentrated under reduced pressure, with toluene azeotropes to remove DMF. Recrystallization of the residual solid from 50 ml of acetonitrile and 100 ml of toluene affords 3.92 g of the title compound.
.sup.1 H NMR .delta. 3.34, 3.80 ppm; IR 1528, 1499, 1448, 1245, 1112, 1036, 906 cm.sup.-1 ; EI MS m/z 186; Anal. Found: C, 38.67; H, 5.48; N, 30.17; S, 17.18.
EXAMPLE 5
Preparation of tert-Butyl N-{2-[(5-amino-1,3,4-thiadiazol-2-yl)amino]ethyl}carbamate. ##STR10##
A mixture of 5-bromo-1,3,4-thiadiazol-2-ylamine (5.40 g), K.sub.2 HPO.sub.4 (7.84 g), and Boc-ethylenediamine (9.6 g) in 20 ml of DMF is stirred at ambient temperature for 18 hours. The solid paste obtained is recrystallized from 100 ml of acetonitrile and 100 ml of water to provide 6.18 g (79%) of the title compound.
.sup.1 H NMR (MeOH-d.sub.4) .delta. 1.40, 3.2-3.3 ppm; IR 2989, 1676, 1577, 1512, 1366 cm.sup.-1 ; EI MS m/z 260; M.p. 219-220.degree. C.
EXAMPLE 6
Preparation of N-[5-(Cycloheptylamino)-1,3,4-thiadiazol-2-yl]-2-ethoxy-1-naphthamide.-ethoxy-1-naphthoyl). ##STR11##
A mixture of 5-bromo-1,3,4-thiadiazol-2-ylamine (720 mg), K.sub.2 HPO.sub.4 (780 mg), and cycloheptylamine (0.51 mg) in 5 ml of DMF is stirred at 60.degree. C. for 4 hours, then diluted with pyridine and centrifuged to remove solids. To one-half of this solution, cooled to 0.degree. C., is added a solution of 469 mg of 2-ethoxy-1-naphthoyl chloride in 5 ml of chloroform. The solution is stirred at room temperature overnight, then concentrated under reduced pressure. Addition of water and ethyl acetate to the residue provides a solid, which is filtered, washed with ethyl acetate and water, and dried under vacuum to afford 200 mg of the title compound as a white solid.
.sup.1 H NMR (CDCl.sub.3) .delta. 1.50, 1.4-1.8, 2.1, 3.6, 4.26, 7.3-7.6, 7.8, 8.0 ppm; HRMS (m+H) 411.1875.
EXAMPLE 7
Preparation of N-[5-(Cycloheptylamino)-1,3,4-thiadiazol-2-yl]-2-methoxybenzamide. ##STR12##
A mixture of 5-bromo-1,3,4-thiadiazol-2-ylamine (720 mg), K.sub.2 HPO.sub.4 (780 mg), and cycloheptylamine (0.51 mg) in 5 ml of DMF is stirred at 60.degree. C. for 4 hours, then diluted with pyridine and centrifuged to remove solids. To one-half of this solution, cooled to 0.degree. C., is added 0.30 ml of o-anisoyl chloride. The solution is stirred at room temperature overnight, then concentrated under reduced pressure and diluted with 100 ml of water. The precipitated solid is filtered, washed with water, and dried under vacuum to afford 641 mg of the title compound.
.sup.1 H NMR (CDC1.sub.3) .delta. 1.4-1.7, 2.1, 3.6, 4.09, 7.0-7.2, 7.6, 8.25 ppm; HRMS m/z 346.1469.
EXAMPLE 8
Preparation of N-{5-[(2,2-Diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}-2-ethoxy-1-naphthamide. ##STR13##
A mixture 5-bromo-1,3,4-thiadiazol-2-ylamine (720 mg), K.sub.2 HPO.sub.4 (780 mg), and 2,2-diphenylethylamine (789 mg) in 5 ml of DMF is stirred at 60.degree. C. for 4 hours, then diluted with pyridine and centrifuged to remove solids. To one-half of this solution, cooled to 0.degree. C., is added a solution of 2-ethoxy-1-naphthoyl chloride (469 mg) in 5 ml of chloroform. The solution is stirred at room temperature overnight, then concentrated under reduced pressure and diluted with 100 ml of water. The resultant solid is filtered, washed with water, and dried under vacuum to provide 947 mg of the title compound.
.sup.1 H NMR (CDCl.sub.3) .delta. 1.43, 4.02, 4.15, 4.26, 4.44, 7.2-7.6, 7.8-8.0 ppm; HRMS (m+H) 495.1846.
EXAMPLE 9
Preparation of 2-Ethoxy-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-1-naphthamide. ##STR14##
A mixture of 5-bromo-1,3,4-thiadiazol-2-ylamine (720 mg), K.sub.2 HPO.sub.4 (780 mg), and tryptamine (641 mg) in 5 ml of DMF is stirred at 60.degree. C. for 12 hours, then diluted with pyridine and centrifuged to remove solids. To one-half of this solution, cooled to 0.degree. C., is added a solution of 469 mg of 2-ethoxy-1-naphthoyl chloride in 5 ml of chloroform. The solution is stirred at room temperature overnight, then concentrated under reduced pressure and diluted with 100 ml of water. The resultant solid is filtered, washed with water, and dried under vacuum to provide 866 mg of white solid. Column chromatography of 249 mg of this on silica, using 1.5-4% methanol in dichloromethane, provides 191 mg of the title compound.
.sup.1 H NMR (CDCl.sub.3) .delta. 1.43, 3.16, 3.70, 4.26, 7.0-7.2, 7.3-7.4, 7.5, 7.6, 7.8, 8.0 ppm; HRMS (m+H) 458.1655.
EXAMPLE 10
Preparation of N-[5-({[(2R)-6,6-Dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)-1,3,4-thiadiazol-2-yl]-2-ethoxy-1-naphthamide. ##STR15##
A mixture of 5-bromo-1,3,4-thiadiazol-2-ylamine (720 mg), K.sub.2 HPO.sub.4 (780 mg), and myrtanylamine (0.67 mg) in 5 ml of DMF is stirred at 60.degree. C. for 12 hours, then diluted with pyridine and centrifuged to remove solids. To one-half of this solution, cooled to 0.degree. C., is added a solution of 2-ethoxy-1-naphthoyl chloride (469 mg) in 5 ml of chloroform. The solution is stirred at room temperature overnight, then concentrated under reduced pressure and diluted with 100 ml of water. The resultant solid is filtered, washed with water, and dried under vacuum to provide 846 mg of solid. Column chromatography of 249 mg of this on silica, using 2-4% methanol in dichloromethane, provides 220 mg of the title compound.
.sup.1 H NMR (CDCl.sub.3) .delta. 1.07, 1.23, 1.44, 1.8-2.1, 2.4, 3.3, 4.27, 7.2-7.6, 7.8, 8.0 ppm; HRMS (m+H) 451.2163.
EXAMPLE 11
The Following 1,3,4-Thiadiazoles of the Present Invention Are Prepared by General Procedure Described Below.
To each 48 solutions of 5-bromo-1,3,4-thiadiazol-2-ylamine (234 mg, 1.3 mmol) in 1.5 ml of DMF is added K.sub.2 HPO.sub.4 (272 mg) and 1.3 mmol of the following amines respectively: phenethylamine, 2-furylmethylamine, 1-(3-aminopropyl)-2-pyrrolidinone, 2-pyridinylmethylamine, N-(2-aminoethyl)-N-phenylamine, 2-(1H-indol-3-yl)ethylamine, cycloheptylamine, cyclohexylmethylamine, (1S,2R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methylamine, 2-(1-pyrrolidinyl)ethylamine, tetrahydro-2-furanylmethylamine, 4-pyridinylmethylamine, 1,3-benzodioxol-5-ylmethylamine, 2-morpholinoethylamine, 1-naphthylmethylamine, 4-fluorobenzylamine, 3-pyridinylmethylamine, 2-piperidinoethylamine, 2-ethylhexylamine, 4-(2-aminoethyl)benzenesulfonamide, N-(3-aminopropyl)-N-cyclohexylamine, 3,4-dichlorobenzylamine, 3,4-dimethoxybenzylamine, 4-phenylbutylamine, 2,2-diphenylethylamine, undecylamine, 3,3-diphenylpropylamine, 2-(2-thienyl)ethylamine, 4-(aminomethyl)benzenesulfonamide, 3-(4-methylpiperazino)propylamine, 3-aminopropanenitrile, 2-(phenylsulfanyl)ethylamine, 2-thienylmethylamine, N-(2-aminoethyl)acetamide, 3-(1H-imidazol-1-yl)propylamine, tert-butyl 3-aminopropanoate, cyclopropylamine, cyclopropylmethylamine, 2-(1H-imidazol-4-yl)ethylamine, 2-(ethylsulfanyl)ethylamine, cyclobutylamine, 2-(1-methyl-2-pyrrolidinyl)ethylamine, 2,3-dihydro-1H-inden-1-ylamine, neopentylamine, 1,2,3,4-tetrahydro-1-naphthalenamine, ethyl 4-aminotetrahydro-1(2H)-pyridinecarboxylate, 1-benzyl-4-piperidinylamine, and N-(2-aminoethyl)-N,N-dimethylamine.
The resultant 48 mixtures are heated at 60.degree. C. for 3 hours to provide a DMF solutions of the corresponding substituted aminothiadiazole intermediates. The solutions of intermediate aminothiadiazoles are diluted with pyridine to a volume of 10.0 ml, and solids are removed by centrifugation. The supernatants are aliquoted into wells of 96-well plates (0.40 ml per well) respectively, and to each well is added 0.26 ml of a 0.2 M chloroform solution of the following acid chlorides respectively: 2,4-difluorobenzoyl chloride, 2-methoxybenzoyl chloride, 4-bromobenzoyl chloride, 4-methylbenzoyl chloride, 5-chloropentanoyl chloride, 4-cyanobenzoyl chloride, 3-nitrobenzoyl chloride, 3,5-difluorobenzoyl chloride, (E)-3-(2-chlorophenyl)-2-propenoyl chloride, 2-ethoxy-1-naphthoyl chloride, (Z)-9-octadecenoyl chloride, 2,6-dichlorobenzoyl chloride, 3,4-dichlorobenzoyl chloride,4-(trifluoromethyl)benzoyl chloride, (E)-3-phenyl-2-propenoyl chloride, 4-iodobenzoyl chloride, 1,3-dioxo-1,3-dihydro-2-benzofuran-5-carbonyl chloride, 4-(fluorosulfonyl)benzoyl chloride, 2,4,6-triisopropylbenzoyl chloride, 5-nitro-2-furoyl chloride, and 1-benzothiophene-2-carbonyl chloride.
The plates are shaken at intervals to effect mixing of reactants, and the acylation is allowed to proceed at room temperature overnight. Removal of the solvents in a stream of air or under vacuum then affords the compounds listed in TABLE 1.
All the amines and acid chlorides used above are either commercially available or can be easily prepared by one having ordinary skill in the organic chemistry art utilizing well known procedures.
In TABLE 1, "MS" refers to mass spectral data, "% inhib" refers to percentage of inhibition at 25 .mu.M concentration in CMV polymerase assay.
TABLE 1__________________________________________________________________________ MS % Inhib__________________________________________________________________________1 (E)-N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4- 520 100.2 thiadiazol-2-yl)-9-octadecenamide 2 N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol- -- 100.1 2-yl)-1,3-dioxo-1,3-dihydro-2-benzofu ran-5-carboxamide 3 N-{5-[(cyclohexylmethyl)amino]-1,3,4-thiadiazol-2-yl}-1,3- 419 100.0 dioxo-1,3-dihydro-2-benzofuran-5-carb oxamide 4 1,3-dioxo-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]-1,3- 443 100.0 dihydro-2-benzofuran-5-carboxamide 5 (E)-N-(5-{[2-(1-methyl-2-pyrrolidiny l)ethyl]amino}-1,3,4- 492 99.9 thiadiazol-2-yl)-9-octadecenamide 6 N-{5-[(2-anilinoethyl)amino]-1,3,4-t hiadiazol-2-yl}-1,3- 410 99.9 dioxo-1,3-dihydro-2-benzofuran-5-carboxamide, 7 N-{5-[(4-fluorobenzyl)amino]-1,3,4-thiadiazol-2-yl}-1,3- 399 99.8 dioxo-1,3-dihydro-2-benzofuran-5-carb oxamide 8 N-{5-[(1-naphthylmethyl)amino]-1,3,4-thiadiazol-2-yl}- 431 99.8 1,3-dioxo-1,3-dihydro-2-benzofuran-5- carboxamide 9 1,3-dioxo-N-(5-{[2-(2-thienyl)ethyl]amino}-1,3,4- 401 99.8 thiadiazol-2-yl)-1,3-dihydro-2-benzofuran-5- carboxamide 10 N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2- 434 99.7 yl)-1,3-dioxo-1,3-dihydro-2-benzofura n-5-carboxamide 11 1,3-dioxo-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2- 421 99.6 yl}-1,3-dihydro-2-benzofuran-5-carbox amide 12 N-{5-[(3,4-dichlorobenzyl)amino]-1,3,4-thiadiazol-2-yl}- 449 99.5 1,3-dioxo-1,3-dihydro-2-benzofuran-5- carboxamide 13 N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2- 483 99.3 yl}-1,3-dioxo-1,3-dihydro-2-benzofura n-5-carboxamide 14 (E)-N-(5-{[3-(4-methylpiperazino)propyl]amino}-1,3,4- 521 99.0 thiadiazol-2-yl)-9-octadecenamide 15 N-(5-{[4-(aminosulfonyl)phenethyl]a mino}-1,3,4-thiadiazol- 474 98.8 2-yl)-1,3-dioxo-1,3-dihydro-2-benzofu ran-5-carboxamide 16 N-{5-[(3,4-dimethoxybenzyl)amino]-1,3,4-thiadiazol-2-yl}- 441 98.7 1,3-dioxo-1,3-dihydro-2-benzofuran-5- carboxamide 17 N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}- 471 98.6 1,3-dioxo-1,3-dihydro-2-benzofuran-5- carboxamide 18 (E)-N-(5-{[4-(aminosulfonyl)benzyl]amino}-1,3,4- -- 98.3 thiadiazol-2-yl)-9-octadecenamide 19 (E)-N-(5-{[2-(1-pyrrolidinyl)ethyl]amino}-1,3,4- 478 97.7 thiadiazol-2-yl)-9-octadecenamide 20 N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4- 425 97.7 thiadiazol-2-yl}-1,3-dioxo-1,3-dihydro-2- benzofuran-5-carboxamide 21 1,3-dioxo-N-[5-(1,2,3,4-tetrahydro-1-naphthalenylamino)- 421 97.4 1,3,4-thiadiazol-2-yl]-1,3-dihydro-2- benzofuran-5- carboxamide 22 N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}- 387 97.2 amino)-1,3,4-thiadiazol-2-yl]-2-metho xybenzamide 23 (E)-N-(5-{[2-(dimethylamino)ethyl]amino}-1,3,4-thiadiazol- 452 97.0 2-yl)-9-octadecenamide 24 1,3-dioxo-N-[5-(phenethylamino)-1,3,4-thiadiazol-2-yl]- 395 95.6 1,3-dihydro-2-benzofuran-5-carboxamid e 25 N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}- 425 93.9 amino)-1,3,4-thiadiazol-2-yl]-1,3-dio xo-1,3-dihydro-2- benzofuran-5-carboxamide 26 N-(5-{[4-(aminosulfonyl)benzyl]amino}-1,3,4-thiadiazol- 484 93.1 2-yl)-2-ethoxy-1-naphthamide 27 N-(5-{[3-(cyclohexylamino)propyl]am ino}-1,3,4- 454 92.9 thiadiazol-2-yl)-2-ethoxy-1-naphthamide 28 (E)-N-[5-(cyclopropylamino)-1,3,4-thiadiazol-2-yl]- 421 92.6 9-octadecenamide 29 N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-1,3-dioxo- 387 92.4 1,3-dihydro-2-benzofuran-5-carboxamid e 30 N-(5-{[4-(aminosulfonyl)benzyl]amino}-1,3,4-thiadiazol- 458 91.8 2-yl)-2,6-dichlorobenzamide 31 (E)-N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-9- 477 91.8 octadecenamide 32 (E)-N-(5-{[4-(aminosulfonyl)benzyl]amino}-1,3,4- 416 90.6 thiadiazol-2-yl)-3-phenyl-2-propenamide 33 1,3-dioxo-N-(5-{[2-(phenylsulfanyl)ethyl]amino}-1,3,4- 425 90.1 thiadiazol-2-yl)-1,3-dihydro-2-benzof uran-5-carboxamide 34 (E)-3-(2-chlorophenyl)-N-{5-[(cyclopropylmethyl)amino]- 335 89.9 1,3,4-thiadiazol-2-yl}-2-propenamide 35 N-(5-{[4-(aminosulfonyl)benzyl]amino}-1,3,4-thiadiazol-2- 516 89.7 yl)-2,4,6-triisopropylbenzamide 36 N-(5-{[3-(cyclohexylamino)propyl]am ino}-1,3,4-thiadiazol- 486 87.6 2-yl)-2,4,6-triisopropylbenzamide 37 2,6-dichloro-N-(5-{[3-(cyclohexylam ino)propyl]amino}- 428 87.4 1,3,4-thiadiazol-2-yl)benzamide 38 (E)-N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}- 561 87.3 9-octadecenamide 39 1,3-dioxo-N-{5-[(2-thienylmethyl)amino]-1,3,4-thiadiazol- 387 87.1 2-yl}-1,3-dihydro-2-benzofuran-5-carb oxamide 40 N-[5-(2,3-dihydro-1H-inden-1-ylamino)-1,3,4-thiadiazol-2- 407 86.3 yl]-1,3-dioxo-1,3-dihydro-2-benzofura n-5-carboxamide 41 (E)-N-(5-{[2-(2-thienyl)ethyl]amino}-1,3,4-thiadiazol-2- 491 85.7 yl)-9-octadecenamide 42 (E)-N-{5-[(2-thienylmethyl)amino]-1,3,4-thiadiazol-2-yl}- 477 84.6 9-octadecenamide 43 N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4-thiadiazol- 449 83.9 2-yl}-2-ethoxy-1-naphthamide 44 N-{5-[(1-naphthylmethyl)amino]-1,3, 4-thiadiazol-2-yl}- 396 83.3 5-nitro-2-furamide 45 N-{5-[(1-benzyl-4-piperidinyl)amino]-1,3,4-thiadiazol-2-yl}- 488 83.1 2-ethoxy-1-naphthamide 46 4-cyano-N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol- 440 82.3 2-yl}benzamide 47 N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2- 399 81.6 yl)-5-nitro-2-furamide 48 (E)-N-{5-[(4-fluorobenzyl)amino]-1,3,4-thiadiazol-2-yl}- 489 81.5 9-octadecenamide 49 4-({[5-(undecylamino)-1,3,4-thiadiazol-2-yl]amino}- -- 80.3 carbonyl)benzenesulfonyl fluoride 50 (E)-N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4- 430 79.8 thiadiazol-2-yl)-3-phenyl-2-propenami de 51 (E)-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]-9- 535 79.5 octadecenamide 52 N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}-1- -- 78.7 benzothiophen-2-carboxamide 53 (E)-N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4- 515 77.9 thiadiazol-2-yl}-9-octadecenamide 54 1,3-dioxo-N-{5-[(4-pyridinylmethyl) amino]-1,3,4- 382 77.7 thiadiazol-2-yl}-1,3-dihydro-2-benzofuran-5-carboxamide 55 N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}- 495 77.6 2-ethoxy-1-naphthamide 56 2,6-dichloro-N-{5-[(2,2-diphenylethyl)amino]-1,3,4- 469 77.4 thiadiazol-2-yl}benzamide 57 N-(5-{[4-(aminosulfonyl)benzyl]amino}-1,3,4- 516 76.3 thiadiazol-2-yl)-4-iodobenzamide 58 (E)-N-(5-{[2-(phenylsulfanyl)ethyl]amino}-1,3,4- 517 75.8 thiadiazol-2-yl)-9-octadecenamide 59 4-iodo-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol- 479 74.6 2-yl}benzamide 60 5-nitro-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]- -- 74.5 2-furamide 61 N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol- 509 74.2 2-yl}-2-ethoxy-1-naphthamide 62 N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4- 416 74.0 thiadiazol-2-yl)-1-benzothiophene-2-carboxamide 63 2,6-dichloro-N-{5-[(3,3-diphenylpropyl)amino] 483 73.8 1,3,4-thiadiazol-2-yl}benzamide 64 (E)-N-{5-[(3,3-diphenylpropyl)amino]-1,3,4- 575 73.6 thiadiazol-2-yl}-9-octadecenamide 65 4-cyano-N-[5-(undecylamino)-1,3,4-thiadiazol- 400 72.2 2-yl]benzamide 66 2-ethoxy-N-{5-[(3-pyridinylmethyl)amino]-1,3,4- 406 71.9 thiadiazol-2-yl}-1-naphthamide 67 (E)-3-(2-chlorophenyl)-N-{5-[(4-fluorobenzyl)amino]- 389 71.7 1,3,4-thiadiazol-2-yl}-2-propenamide 68 N-(5-{[4-(aminosulfonyl)phenthyl]amino}-1,3,4- 530 71.1 thiadiazol-2-yl)-4-iodobenzamide 69 N-{5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2-yl}- 434 70.6 2-ethoxy-1-naphthamide 70 2-ethoxy-N-{5-[(2-pyridinylmethyl)amino]-1,3,4- 406 70.4 thiadiazol-2-yl}-1-naphthamide 71 2-ethoxy-N-{5-[(4-fluorobenzyl)amino]-1,3,4- 423 69.8 thiadiazol-2-yl}-1-naphthamide 72 (E)-N-{5-[(3-pyridinylmethyl)amino]-1,3,4- 470 69.3 thiadiazol-2-yl}-9-octadecenamide 73 2,6-dichloro-N-{5-[(3,4-dichlorobenzyl)amino]- 449 69.1 1,3,4-thiadiazol-2-yl}benzamide 74 4-cyano-N-{5-[(4-fluorobenzyl)amino]-1,3,4- 354 69.0 thiadiazol-2-yl}benzamide 75 (E)-3-(2-chlorophenyl)-N-(5-{[3-(cyclohexylamino)- 420 68.8 propyl]amino}-1,3,4-thiadiazol-2-yl)-2-propenamide 76 2,6-dichloro-N-[5-(1,2,3,4-tetrahydro-1-naphthalenyl- 419 68.5 amino)-1,3,4-thiadiazol-2-yl]benzamid e 77 (E)-3-phenyl-N-(5-{[2-(2-thienyl)ethyl]amino}-1,3,4- 357 68.3 thiadiazol-2-yl)-2-propenamide 78 2-ethoxy-N-{5-[(2-thienylmethyl)ami no]-1,3,4-thiadiazol- 411 68.2 2-yl}-1-naphthamide 79 tert-butyl-3-({5-[(E)-9-octadecenoylamino]-1,3,4- -- 68.0 thiadiazol-2-yl}amino)propanoate 80 3-nitro-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]- -- 67.9 benzamide 81 (E)-3-phenyl-N-{5-[(4-phenylbutyl)amino]-1,3,4- 379 67.9 thiadiazol-2-yl}-2-propenamide 82 4-cyano-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}- 389 67.7 1,3,4-thiadiazol-2-yl)benzamide 83 4-cyano-N-{5-[(2,2-diphenylethyl)amino]-1,3,4- 426 67.7 thiadiazol-2-yl}benzamide 84 2,6-dichloro-N-{5-[(4-pyridinylmethyl)amino]- 380 67.6 1,3,4-thiadiazol-2-yl}benzamide 85 N-{5-[(1-benzyl-4-piperidinyl)amino]-1,3,4- 464 67.3 thiadiazol-2-yl}-1,3-dioxo-1,3-dihydro-2-benzofuran- 5-carboxamide 86 ethyl 4-[(5-{[(2-ethoxy-1-naphthyl)carbonyl]amino}- 470 67.0 1,3,4-thiadiazol-2-yl)amino]tetrahydr o-1(2H)- pyridinecarboxylate 87 N-(5-{[3-(1H-imidazol-1-yl)propyl]amino}-1,3,4- 455 67.0 thiadiazol-2-yl)-2,4,6-triisopropylbenzamide 88 (E)-N-(5-{[4-(aminosulfonyl)benzyl]amino}-1,3,4- 450 66.5 thiadiazol-2-yl)-3-(2-chlorophenyl)-2-propenamide 89 2-ethoxy-N-(5-{[2-(1H-imidazol-4-yl)ethyl]amino}- 409 66.3 1,3,4-thiadiazol-2-yl)-1-naphthamide 90 4-{[(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4- 446 66.1 thiadiazol-2-yl)amino]carbonyl}benzenesulfonyl fluoride 91 ethyl 4-({5-[(E)-9-octadecenoylamino]-1,3,4-thiadiazol- 272 66.1 2-yl}amino)tetrahydro-1(2H)-pyridinec arboxylate 92 2,6-dichloro-N-(5-{[2-(2-thienyl)ethyl]amino}-1,3,4- 399 66.1 thiadiazol-2-yl)benzamide 93 2-ethoxy-N-[5-(1,2,3,4-tetrahydro-1-naphthaienylamino)- 445 66.0 1,3,4-thiadiazol-2-yl]-1-naphthamide 94 (E)-3-phenyl-N-{5-[(4-pyridinylmethyl)amino]-1,3,4- 338 65.9 thiadiazol-2-yl}-2-propenamide 95 N-[5-(2,3-dihydro-1H-inden-1-ylamin o)-1,3,4-thiadiazol- 431 65.9 2-yl]-2-ethoxy-1-naphthamide 96 N-{5-[(1,3-benzodioxol-5-ylethyl)amino]-1,3,4-thiadiazol- 423 65.9 2-yl}-2,6-dichlorobenzamide 97 2-ethoxy-N-(5-{[2-(2-thienyl)ethyl]amino}-1,3,4- 425 65.8 thiadiazol-2-yl)-1-naphthamide 98 (E)-3-(2-chlorophenyl)-N-(5-{[2-(1H-imidazol-4-yl)ethyl]- 375 65.7 amino}-1,3,4-thiadiazol-2-yl)-2-prope namide 99 2,6-dichloro-N-(5-{[3-(1H-imidazol-1-yl)propyl]amino}- 397 65.6 1,3,4-thiadiazol-2-yl)benzamide 100 (E)-N-{5-[(3,4-dimethoxybenzyl)ami no]-1,3,4-thiadiazol- -- 65.1 2-yl}-9-octadecenamide 101 2,6-dichloro-N-{5-[(1-naphthylmethyl)amino]-1,3,4- 429 65.0 thiadiazol-2-yl}benzamide 102 4-cyano-N-(5-{[2-(2-thienyl)ethyl]amino}-1,3,4- 356 64.9 thiadiazol-2-yl)benzamide 103 4-cyano-N-[5-(cycloheptylamino)-1,3,4-thiadiazol- 342 64.9 2-yl]benzamide 104 N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-5- 352 64.7 nitro-2-furamide 105 (E)-N-[5-(phenethylamino)-1,3,4-thiadiazol-2-yl]- 485 64.6 9-octadecenamide, 106 5-chloro-N-[5-(undecylamino)-1,3,4-thiadiazol-2- 389 64.2 yl]pentanamide, 107 (E)-N-[5-(1,2,3,4-tetrahydro-1-naphthalenylamino)- 511 63.8 1,3,4-thiadiazol-2-yl]-9-octadecenami de 108 (E)-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}- 513 63.5 9-octadecenamide 109 2,4,6-triisopropyl-N-(5-{[2-(1-methyl-2-pyrrolidinyl)ethyl] 458 63.4 amino]-1,3,4-thiadiazol-2-yl)benzamide 110 (E)-N-{5-[(1-benzyl-4-piperidinyl)amino]-1,3,4-thiadiazol- 454 62.9 2-yl}-3-(2-chlorophenyl)-2-propenamide 111 4-[({5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2- 483 62.6 yl}amino)carbonyl]benzenesulfonyl fluoride 112 N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4- 428 62.5 thiadiazol-2-yl)-4-(trifluoromethyl)benzamide 113 (E)-N-{5-[(cyclopropylmethyl)amino]-1,3,4-thiadiazol- 435 62.2 2-yl}-9-octadecenamide 114 (E)-3-phenyl-N-(5-{[2-(phenylsulfanyl)ethyl]amino}- 383 62.1 1,3,4-thiadiazol-2-yl)-2-propenamide 115 2,6-dichloro-N-[5-(2,3-dihydro-1H-inden-1-ylamino)- 405 62.0 1,3,4-thiadiazol-2-yl]benzamide 116 N-{5-[(2-ethylhexyl)amino]-1,3,4-t hiadiazol-2-yl}- 401 61.9 1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide 117 (E)-N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]- 415 61.5 1,3,4-thiadiazol-2-yl}-3-(2-chlorophenyl)-2-propenamide 118 2,6-dichloro-N-{5-[(2-thienylmetyl)amino]-1,3,4- 385 61.2 thiadiazol-2-yl}benzamide 119 (E)-N-{5-[(1-naphthylmethyl)amino]-1,3,4-thiadiazol- 521 60.6 2-yl}-9-octadecenamide 120 tert-butyl 3-[(5-{[(E)-3-phenyl-2-propenoyl]amino}- 375 60.0 1,3,4-thiadiazol-2-yl)amino]propanoat e 121 2,4-difluoro-N-[5-(undecylamino)-1,3,4-thiadiazol-2- 411 60.0 yl]benzamide 122 N-{5-[(3,4-dimethoxybenzyl)amino]-1,3,4-thiadiazol- 465 59.5 2-yl}-2-ethoxy-1-naphthamide 123 (E)-N-(5-{[2-(acetylamino)ethyl]am ino}-1,3,4- 466 59.2 thiadiazol-2-yl)-9-octadecenamide 124 (E)-N-(5-{[3-(cyclohexylamino)propyl]amino}- 386 59.2 1,3,4-thiadiazol-2-yl)-3-phenyl-2-propenamide 125 (E)-N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4- 464 58.9 thiadizol-2-yl)-3-(2-chlorophenyl)-2- propenamide 126 N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4- 395 58.9 thiadiazol-2-yl)-5-nitro-2-furamide 127 4-cyano-N-(5-{[3-(cyclohexylamino)propyl]amino- 385 58.5 1,3,4-thiadiazol-2-yl)benzamide 128 N-(5-{[4-(aminosulfonyl)phenethyl]amino}1,3,4- 530 58.3 thiadiazol-2-yl)-2,4,6-triisopropylbenzamide 129 (E)-N-(5-{[2-(ethylsulfanyl)ethyl]amino}1,3,4- 469 58.3 thiadiazol-2-yl)-9-octadecenamide 130 (E)-N-(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]amino}- 372 58.2 1,3,4-thiadiazol-2-yl)-3-phenyl-2-propenamide 131 5-nitro-N-{5-[(4-phenylbutyl)amino]-1,3,4- 388 58.0 thiadiazol-2-yl}-2-furamide 132 ethyl 4-({5-[(2,6-dichlorobenzoyl)amino]-1,3,4- 444 57.0 thiadiazol-2-yl}amino)tetrahydro-1(2H)- pyridinecarboxylate 133 (E)-N-(5-{[3-(1H-imidazol-1-yl)propyl]amino}- 355 57.0 1,3,4-thiadiazol-2-yl)-3-phenyl-2-propenamide 134 N-{5-[(3,4-dimethoxybenzyl)amino]-1,3,4- 497 56.9 thiadiazol-2-yl}-4-iodobenzamide 135 3-nitro-N-(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]- 391 56.6 amino}-1,3,4-thiadiazol-2-yl)benzamide 136 2-ethoxy-N-{5-[(1-naphthylmethyl)amino]-1,3,4- 455 56.5 thiadiazol-2-yl}-1-naphthamide 137 N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4- 405 56.4 thiadiazol-2-yl)-3-nitrobenzamide 138 N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}- 421 56.2 4-(trifluoromethyl)benzamide 139 (E)-3-phenyl-N-{5-[(2-pyridinylmet hyl)amino]- 338 56.2 1,3,4-thiadiazol-2-yl}-2-propenamide 140 4-cyano-N-{5-[(3,4-dichlorobenzyl)amino]-1,3,4- 404 56.2 thiadiazol-2-yl}benzamide 141 2-ethoxy-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}- 458 55.7 1,3,4-thiadiazol-2-yl)-1-naphthamide 142 N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4- 472 55.4 thiadiazol-2-yl)-3,4-dichlorobenzamide 143 4-cyano-N-{5-[(4-phenylbutyl)amino]-1,3,4- 378 55.4 thiadiazol-2-yl}benzamide 144 2,6-dichloro-N-{5-[(4-fluorobenzyl)amino]-1,3,4- 397 55.2 thiadiazol-2-yl}benzamide 145 2-ethoxy-N-[5-(undecylamino)-1,3,4-thiadiazol- 469 54.9 2-yl]-1-naphthamide 146 2,6-dichloro-N-{5-[(2-cyanoethyl)amino]-1,3,4- 342 54.8 thiadiazol-2-yl}benzamide 147 4-iodo-N-[5-(undecylamino)-1,3,4-thiadiazol-2- 501 54.7 yl]benzamide 148 N-(5-{[2-(ethylsulfanyl)ethyl]amino}-1,3,4- 435 54.6 thiadiazol-2-yl)-4-iodobenzamide 149 (E)-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4- 524 54.5 thiadiazol-2-yl)-9-octadecenamide 150 N-(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]amino}- 402 54.5 1,3,4-thiadiazol-2-yl)-1-benzothiophene-2-carboxamide 151 N-{5-[(1-benzyl-4-piperidinyl)amino]-1,3,4-thiadiazol- 462 54.0 2-yl}-2,6-dichlorobenzamide 152 N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4- 484 53.9 thiadiazol-2-yl)-4-bromobenzamide 153 (E)-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4- 390 53.7 thiadiazol-2-yl)-3-phenyl-2-propenamide 154 (E)-3-(2-chlorophenyl)-N-{5-[(2,2-diphenylethyl)amino]- -- 53.6 1,3,4-thiadiazol-2-yl}-2-propenamide 155 4-cyano-N-{5-[(1-naphthylmethyl)amino]-1,3,4-thiadiazol-2- 386 53.3 yl}benzamide 156 2,6-dichloro-N-{5-[(3-pyridinylmethyl)amino]-1,3,4- 380 53.2 thiadiazol-2-yl}benzamide 157 N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-2-ethoxy-1- 411 53.0 naphthamide 158 4-cyano-N-(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]amino}- 371 52.9 1,3,4-thiadiazol-2-yl)benzamide 159 4-bromo-N-(5-{[3-(cyclohexylamino) propyl]amino}-1,3,4- 440 52.8 thiadiazol-2-yl)benzamide 160 N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4- 396 52.6 thiadiazol-2-yl)-2,4-difluorobenzamide 161 (E)-3-(2-chlorophenyl)-N-{5-[(2-pyridinylmethyl)amino]- 372 51.9 1,3,4-thiadiazol-2-yl}-2-propenamide 162 N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2- 374 51.8 yl)-4-methylbenzamide 163 4-bromo-N-(5-{[2-(phenylsulfanyl)ethyl]amino}-1,3,4- 437 51.5 thiadiazol-2-yl)benzamide 164 (E)-3-(2-chlorophenyl)-N-{5-[(2-thienylmethyl)amino]-1,3,4- 377 51.4 thiadiazol-2-yl}-2-propenamide 165 N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4-thiadiazol-2- 369 51.3 yl}-5-chloropentanamide 166 (E)-N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}- 517 51.1 amino)-1,3,4-thiadiazol-2-yl]-9-octadecenamide 167 4-methyl-N-[5-(undecylamino)-1,3,4-thiadiazol-2- 389 50.8 yl]benzamide 168 3,4-dichloro-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2- 421 50.8 yl}benzamide 169 2,4,6-triisopropyl-N-(5-{[2-(1-pyrrolidinyl)ethyl]amino}-1,3,4- 444 50.7 thiadiazol-2-yl)benzamide 170 4-bromo-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2- 433 50.5 yl}benzamide 171 (E)-N-{5-[(2-pyridinylmethyl)amino]-1,3,4-thiadiazol-2-yl}-9- 472 49.9 octadecenamide 172 3,4-dichloro-N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4- 428 49.7 thiadiazol-2-yl)benzamide 173 2,4,6-triisopropyl-N-{5-[(1-naphthylmethyl)amino]-1,3,4- 487 49.5 thiadiazol-2-yl}benzamide 174 2,6-dichloro-N-{5-[(2-furylmethyl)amino]-1,3,4-thiadiazol-2- 369 49.5 yl}benzamide 175 3,5-difluoro-N-[5-(undecylamino)-1,3,4-thiadiazol-2- 411 49.4 yl]benzamide 176 N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}-2,4,6- 527 49.4 triisopropylbenzamide 177 N-{5-[(cyclopropylmethyl)amino]-1,3,4-thiadiazol-2- 369 49.0 yl}-2-ethoxy-1-naphthamide 178 (E)-N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4- 381 49.0 thiadiazol-2-yl}-3-phenyl-2-propenami de 179 (E)-N-{5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2- 500 48.5 yl}-9-octadecenamide 180 N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4- -- 48.4 thiadiazol-2-yl}-1-benzothiophene-2-carboxamide 181 N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]1,3,4- 369 48.3 thiadiazol-2-yl}-4-methylbenzamide 182 N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2- 437 48.2 yl}-2,4-difluorobenzamide 183 5-chloro-N-{5-[(3,3-diphenylpropyl)amino]-1,3,4- 429 48.1 thiadiazol-2-yl}pentanamide 184 1,3-dioxo-N-(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]amino}- 434 47.8 1,3,4-thiadiazol-2-yl)-1,3-dihydro-2- benzofuran-5-carboxamide 185 (E)-3-(2-chlorophenyl)-N-(5-{[2-(2-thienyl)ethyl]amino}-1,3,4- 391 47.6 thiadiazol-2-yl)-2-propenamide 186 5-chloro-N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2- 415 47.4 yl}pentanamide 187 N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}-1- -- 47.2 benzothiophene-2-carboxamide 188 N-{5-[(2,2-diphenylethyl)amino]-1, 3,4-thiadiazol-2- 437 47.2 yl}-3,5-difluorobenzamide 189 4-{[(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4- 442 47.1 thiadiazol-2-yl)amino]carbonyl}benzenesulfonyl fluoride 190 N-{5-[(1-naphthylmethyl)amino]-1,3,4-thiadiazol-2- 406 47.1 yl}-3-nitrobenzamide 191 3,4-dichloro-N-(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]- 414 47.1 amino}-1,3,4-thiadiazol-2-yl)benzamid e 192 5-nitro-N-[5-(1,2,3,4-tetrahydro-1-naphthalenylamino)- 386 47.0 1,3,4-thiadiazol-2-yl]-2-furamide 193 (E)-3-(2-chlorophenyl)-N-(5-{[2-(e thylsulfanyl)ethyl] 369 46.9 amino}-1,3,4-thiadiazol-2-yl)-2-propenamide 194 4-bromo-N-[5-(undecylamino)-1,3,4-thiadiazol-2- 455 46.8 yl]benzamide 195 4-[({5-[(1-naphthylmethyl)amino]-1,3,4-thiadiazol-2- 443 46.7 yl}amino)carbonyl]benzenesulfonyl fluoride 196 (E)-3-(2-chlorophenyl)-N-[5-(cycloheptylamino) 1,3,4- 377 46.2 thiadiazol-2-yl]-2-propenamide 197 2,4-difluoro-N-{5-[(4-phenylbutyl) amino]-1,3,4- 389 46.2 thiadiazol-2-yl}benzamide 198 4-iodo-N-(5-{[2-(phenylsulfanyl)ethyl]amino}-1,3,4- -- 46.0 thiadiazol-2-yl)benzamide 199 (E)-N-[5-(cyclobutylamino)-1,3,4-thiadiazol-2-yl]-9- 435 46.0 octadecenamide 200 5-chloro-N-{5-[(1-naphthylmethyl)amino]-1,3,4- 375 45.3 thiadiazol-2-yl}pentanamide 201 N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2- 362 45.3 yl]-3-nitrobenzamide 202 3,4-dichloro-N-(5-{[3-(1H-imidazol-1-yl)propyl]amino}- 397 45.0 1,3,4-thiadiazol-2-yl)benzamide 203 4-iodo-N-(5-{[3-(2-oxo-1-pyrrolidi nyl)propyl]amino}- 472 45.0 1,3,4-thiadiazol-2-yl)benzamide 204 4-[({5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2- 422 45.0 yl}amino)carbonyl]benzenesulfonyl fluoride 205 2,4-difluoro-N-(5-{[2-(phenylsulfanyl)ethyl]amino}- 393 44.9 1,3,4-thiadiazol-2-yl)benzamide 206 2-ethoxy-N-(5-{[2-(phenylsulfanyl) ethyl]amino}-1,3,4- 451 44.9 thiadiazol-2-yl)-1-naphthamide 207 N-{5-[(3,4-dichlorobenzyl)amino]-1,3,4-thiadiazol-2-yl}-2- 473 44.7 ethoxy-1-naphthamide 208 (E)-3-(2-chlorophenyl)-N-(5-{[3-(2-oxo-1-pyrrolidinyl)- 406 44.7 propyl]amino}-1,3,4-thiadiazol-2-yl)- 2-propenamide 209 N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}- 392 44.7 amino)-1,3,4-thiadiazol-2-yl]-5-nitro -2-furamide 210 (E)-3-(2-chlorophenyl)-N-[5-(phenethylamino)-1,3,4- 385 44.6 thiadiazol-2-yl]-2-propenamide 211 (E)-N-(5-{[2-(ethylsulfanyl)ethyl] amino}-1,3,4-thiadiazol- 335 44.3 2-yl)-3-phenyl-2-propenamide 212 N-(5-{[3-(cyclohexylamino)propyl]a mino}-1,3,4-thiadiazol- 486 44.2 2-yl)-4-iodobenzamide 213 2-ethoxy-N-{5-[(2-furylmethyl)amino]-1,3,4-thiadiazol-2- 395 44.2 yl}-1-naphthamide 214 N-{5-[(1-naphthylmethyl)amino]-1,3,4-thiadiazol-2-yl}-1- -- 44.1 benzothiophene-2-carboxamide 215 (E)-N-(5-{[2-(1H-imidazol-4-yl)eth yl]amino}-1,3,4-thiadiazol- 341 44.1 2-yl)-3-phenyl-2-propenamide 216 (E)-3-(2-chlorophenyl)-N-[5-(undec ylamino)-1,3,4-thiadiazol- -- 43.9 2-yl]-2-propenamide 217 4-[({5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2- 497 43.9 yl}amino)carbonyl]benzenesulfonyl fluoride 218 N-{5-[(1-benzyl-4-piperidinyl)amino]-1,3,4- 450 43.6 thiadiazol-2-yl}-1-benzothiophene-2-carboxamide 219 N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)- 490 43.6 2,4,6-triisopropylbenzamide 220 (E)-N-{5-[(2-morpholinoethyl)amino]-1,3,4-thiadiazol-2-yl}- 360 43.6 3-phenyl-2-propenamide 221 (E)-3-(2-chlorophenyl)-N-(5-{[3-(1H-imidazol-1-yl)propyl] 389 43.5 amino}-1,3,4-thiadiazol-2-yl)-2-prope namide 222 N-{5-[(4-pyridinylmethyl)amino]-1,3,4-thiadiazol-2-yl}-1- 368 43.2 benzothiophene-2-carboxamide 223 N-(5-{[4-(aminosulfonyl)benzyl]ami no}-1,3,4-thiadiazol-2- 446 43.1 yl)-1-benzothiophene-2-carboxamide 224 N-{5-[(2,2-diphenylethyl)amino]-1, 3,4-thiadiazol-2-yl}-2- 431 43.0 methoxybenzamide 225 2,6-dichloro-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol- 421 42.9 2-yl}benzamide 226 N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}- 460 42.9 3-nitrobenzamide 227 N-[5-(cyclopropylamino)-1,3,4-thiadiazol-2-yl]-2-ethoxy-1- 355 42.8 naphthamide 228 3,5-difluoro-N-(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]amino}- 382 42.8 1,3,4-thiadiazol-2-yl)benzamide 229 271 42.5 230 N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4-thiadiazol- 418 42.3 2-yl)-4-methylbenzamide 231 2-ethoxy-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}- 447 42.3 1-naphthamide 232 2,4,6-triisopropyl-N-{5-[(2-piperidinoethyl)amino]-1,3,4- 458 42.2 thiadiazol-2-yl}benzamide 233 2-ethoxy-N-[5-(neopentylamino)-1,3,4-thiadiazol-2-yl]- 385 42.1 1-naphthamide 234 N-(5-{[2-(2-thienyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-1- 387 42.0 benzothiophene-2-carboxamide 235 257 41.8 236 N-{5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2-yl}-1- 396 41.6 benzothiophene-2-carboxamide 237 N-{5-[(2-thienylmethyl)amino]-1,3, 4-thiadiazol-2-yl}-1- 373 41.5 benzothiophene-2-carboxamide 238 (E)-N-{5-[(2-furylmethyl)amino]-1, 3,4-thiadiazol-2-yl}-9- 461 41.5 octadecenamide 239 4-(trifluoromethyl)-N-[5-(undecylamino)-1,3,4-thiadiazol-2- 443 41.4 yl]benzamide 240 (E)-3-(2-chlorophenyl)-N-{5-[(3,3-diphenylpropyl)amino]- -- 41.3 1,3,4-thiadiazol-2-yl}-2-propenamide 241 2,6-dichloro-N-{5-[(2-pyridinylmethyl)amino]-1,3,4-thiadiazol- 380 41.3 2-yl}benzamide 242 2-ethoxy-N-(5-{[3-(1H-imidazol-1-yl)propyl]amino}-1,3,4- 423 41.3 thiadiazol-2-yl)-1-naphthamide 243 N-{5-[(3,3-diphenylpropyl)amino]-1 ,3,4-thiadiazol-2-yl}- 451 41.1 2,4-difluorobenzamide 244 4-cyano-N-{5-[(3,4-dimethoxybenzyl)amino]-1,3,4-thiadiazol- 396 41.0 2-yl}benzamide 245 4-[({5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2- 435 41.0 yl}amino)carbonyl]benzenesulfonyl fluoride 246 (E)-N-{5-[(tetrahydro-2-furanylmethyl)amino]-1,3,4- 465 40.9 thiadiazol-2-yl}-9-octadecenamide 247 3,4-dichloro-N-{5-[(2-furylmethyl) amino]-1,3,4-thiadiazol-2- 369 40.9 yl}benzamide 248 N-{5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2-yl}-2,4,6- 466 40.8 triisopropylbenzamide 249 (E)-N-{5-[(2-cyanoethyl)amino]-1,3,4-thiadiazol-2-yl}- 432 40.6 9-octadecenamide 250 N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-2,4,6- 443 40.5 triisopropylbenzamide 251 (E)-3-(2-chlorophenyl)-N-{5-[(2-furylmethyl)amino]-1,3,4- 361 40.3 thiadiazol-2-yl}-2-propenamide 252 N-(5-{[2-(1H-indol-3-yl)ethyl]amin o}-1,3,4-thiadiazol-2-yl)- 490 40.2 4-iodobenzamide 253 (E)-N-{5-[(1-benzyl-4-piperidinyl)amino]-1,3,4-thiadiazol-2- 554 40.1 yl}-9-octadecenamide 254 5-chloro-N-(5-{[2-(phenylsulfanyl)ethyl]amino]-1,3,4- 371 40.0 thiadiazol-2-yl)pentanamide 255 2,6-dichloro-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4- 432 39.9 thiadiazol-2-yl)benzamide 256 N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-1-benzothiophene- 373 39.8 2-carboxamide 257 N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]-1-benzothiophene- -- 39.8 2-carboxamide 258 N-(5-{[2-(acetylamino)ethyl]amino}-1,3,4-thiadiazol-2-yl)- 376 39.7 1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide 259 N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4-thiadiazol-2- 472 39.6 yl)-2,6-dichlorobenzamide 260 2,4,6-triisopropyl-N-{5-[(4-phenylbutyl)amino]-1,3,4- 479 39.6 thiadiazol-2-yl}benzamide 261 N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)- 451 39.5 1,3,4-thiadiazol-2-yl]-2-ethoxy-1-naphthamide 262 (E)-N-[5-(phenethylamino)-1,3,4-thiadiazol-2-yl]-3- 351 39.5 phenyl-2-propenamide 263 3,4-chloro-N-{5-[(4-pyridinylmethyl)amino]-1,3,4- 380 39.4 thiadiazol-2-yl}benzamide 264 N-{5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2-yl}-5- 375 39.2 nitro-2-furamide 265 N-{5-[(1-benzyl-4-piperidinyl)amino]-1,3,4-thiadiazol- 520 39.1 2-yl}-2,4,6-triisopropylbenzamide 266 2,4,6-triisopropyl-N-{5-[(4-pyridi nylmethyl)amino]-1,3,4- 438 38.8 thiadiazol-2-yl}benzamide 267 N-(5-{[4-(aminosulfonyl)phenethyl]amino}- 460 38.7 1,3,4-thiadiazol-2-yl)-1-benzothiophene-2-carboxamide 268 (E)-3-(2-chlorophenyl)-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}- -- 38.7 1,3,4-thiadiazol-2-yl)-2-propenamide 269 N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-1- -- 38.5 benzothiophene-2-carboxamide 270 2-ethoxy-N-[5-(phenethylamino)-1,3,4-thiadiazol-2-yl]-1- 419 38.4 naphthamide 271 N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)- 409 38.4 3-nitrobenzamide 272 4-bromo-N-(5-{[3-(1H-imidazol-1-yl)propyl]amino}-1,3,4- 409 38.2 thiadiazol-2-yl)benzamide 273 N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4-thiadiazol- 435 38.1 2-yl}-4-bromobenzamide 274 (E)-N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-3- 343 38.1 phenyl-2-propenamide 275 N-(5-{[3-(cyclohexylamino)propyl]amino]-1,3,4-thiadiazol-2- 396 37.9 yl)-3,5-difluorobenzamide 276 (E)-3-(2-chlorophenyl)-N-[5-(cyclobutylamino)-1,3,4- 335 37.9 thiadiazol-2-yl]-2-propenamide 277 N-{5-[(3,3-diphenylpropyl)amino]-1 ,3,4-thiadiazol-2- -- 37.9 yl}-1-benzothiophene-2-carboxamide 278 4-({[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl] 399 37.5 amino}carbonyl)benzenesulfonyl fluoride 279 (E)-N-[5-(2,3-dihydro-1H-inden-1-ylamino)-1,3,4- 497 37.4 thiadiazol-2-yl]-9-octadecenamide 280 2,6-dichloro-N-{5-[(3,4-dimethoxybenzyl)amino]-1,3,4- 439 37.3 thiadiazol-2-yl}benzamide 281 N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}- 451 37.3 3,5-difluorobenzamide 282 5-nitro-N-[5-(phenethylamino)-1,3,4-thiadiazol-2-yl]-2- 360 37.1 furamide 283 2,6-dichloro-N-{5-[(2-ethylhexyl)amino]-1,3,4-thiadiazol-2- 401 37.0 yl}benzamide 284 N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol- 432 36.7 2-yl)-4-(trifluoromethyl)benzamide 285 (E)-N-{5-[(cyclohexylmethyl)amino] -1,3,4-thiadiazol-2-yl}-9- 477 36.7 octadecenamide 286 (E)-N-{5-[(2-ethylhexyl)amino]-1,3,4-thiadiazol-2-yl}-9- 493 36.3 octadecenamide 287 N-[5-(cyclopropylamino)-1,3,4-thiadiazol-2-yl]-1- 317 36.2 benzothiophene-2-carboxamide 288 N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2- 443 36.2 yl]-4-iodobenzamide 289 4-iodo-N-{5-[(4-pyridinylmethyl)amino]-1,3,4-thiadiazol- 438 36.0 2-yl}benzamide 290 (E)-N-{5-[(1-benzyl-4-piperidinyl)amino]-1,3,4-thiadiazol- 420 35.9 2-yl}-3-phenyl-2-propenamide 291 N-{5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2-yl}-3- 385 35.7 nitrobenzamide 292 2,6-dichloro-N-(5-{[2-(ethylsulfanyl)ethyl]amino}-1,3,4- 377 35.6 thiadiazol-2-yl)benzamide 293 tert-butyl 3-[(5-{[(2-ethoxy-1-naphthyl)carbonyl]amino}- 443 35.5 1,3,4-thiadiazol-2-yl)amino]propanoat e 294 (E)-N-{5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2-yl}- 400 35.4 3-(2-chlorophenyl)-2-propenamide 295 3,4-dichloro-N-(5-{[2-(1H-indol-3- yl)ethyl]amino}-1,3,4- -- 35.4 thiadiazol-2-yl)benzamide 296 5-nitro-N-(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]amino}-1,3,4- 381 35.1 thiadiazol-2-yl)-2-furamide 297 N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}- -- 35.0 4-iodobenzamide 298 N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}- 450 35.0 5-nitro-2-furamide 299 N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2- 541 34.9 yl}-2,4,6-triisopropylbenzamide 300 N-[5-(cycloheptylamino)-1,3,4-thia diazol-2-yl]-3,5- 353 34.9 difluorobenzamide 301 N-{5-[(3-pyridinylmethyl)amino]-1,3,4-thiadiazol-2-yl}-1- 368 34.8 benzothiophene-2-carboxamide 302 N-{5-[(4-fluorobenzyl)amino]-1,3,4 -thiadiazol-2-yl}-3- 374 34.8 nitrobenzamide 303 N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-2- 394 34.7 methoxybenzamide 304 N-{5-[(cyclohexylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2- 347 34.6 methoxybenzamide 305 N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4- 391 34.5 thiadiazol-2-yl}-2,4-difluorobenzamide 306 N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2- 436 34.4 yl}-5-nitro-2-furamide 307 4-cyano-N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2- 382 34.2 yl]methyl}amino)-1,3,4-thiadiazol-2-y l]benzamide 308 2,4-dichloro-N-[5-(phenethylamino)-1,3,4-thiadiazol-2- 393 34.2 yl]benzamide 309 4-bromo-N-(5-{[2-(ethylsulfanyl)ethyl]amino}-1,3,4- 389 34.0 thiadiazol-2-yl)benzamide 310 N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-2- 347 34.0 methoxybenzamide 311 N-(5-{[4-(aminosulfonyl)benzyl]amino}-1,3,4- 458 33.9 thiadiazol-2-yl)-3,4-dichlorobenzamide 312 5-chloro-N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2- 371 33.9 yl]methyl}amino)-1,3,4-thiadiazol-2-y l]pentanamide 313 (E)-N-{5-[(3,4-dichlorobenzyl)amino]-1,3,4-thiadiazol-2- 539 33.9 yl}-9-octadecenamide 314 N-[5-(cyclobutylamino)-1,3,4-thiadiazol-2-yl]-2-ethoxy-1- 369 33.8 naphthamide 315 5-chloro-N-{5-[(cyclohexylmethyl)amino]-1,3,4- 331 33.8 thiadiazol-2-yl}pentanamide 316 5-chloro-N-[5-(cycloheptylamino)-1,3,4- 331 33.6 thiadiazol-2-yl]pentanamide 317 N-(5-{[2-(1H-imidazol-4-yl)ethyl]amino}-1,3,4- 411 33.6 thiadiazol-2-yl)-2,4,6-triisopropylbenzamide 318 2-ethoxy-N-(5-{[2-(ethylsulfanyl)ethyl]amino}-1,3,4- 403 33.6 thiadiazol-2-yl)-1-naphthamide 319 (E)-3-(2-chlorophenyl)-N-[5-(neope ntylamino)-1,3,4- 351 33.5 thiadiazol-2-yl]-2-propenamide 320 (E)-3-(2-chlorophenyl)-N-[5-({[(2R)-6,6-dimethylbicyclo -- 33.5 [3.1.1]hept-2-yl]methyl}amino)-1,3,4- thiadiazol-2-yl]-2- propenamide 321 5-chloro-N-{5-[(4-fluorobenzyl)amino]-1,3,4-thiadiazol-2- 343 33.2 yl}pentanamide 322 (E)-3-(2-chlorophenyl)-N-(5-{[2-(phenylsulfanyl)ethyl]amino}- -- 33.2 1,3,4-thiadiazol-2-yl)-2-propenamide 323 N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-4- 331 33.0 methylbenzamide 324 N-(5-{[3-(1H-imidazol-1-yl)propyl]amino}-1,3,4- 455 32.9 thiadiazol-2-yl)-4-iodobenzamide 325 5-chloro-N-(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]amino}- 360 32.8 1,3,4-thiadiazol-2-yl)pentanamide 326 (E)-N-{5-[(4-fluorobenzyl)amino]-1 ,3,4-thiadiazol-2-yl}-3- 355 32.7 phenyl-2-propenamide 327 2-methoxy-N-[5-(phenethylamino)-1,3,4-thiadiazol-2- 355 32.5 yl]benzamide 328 N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4-thiadiazol- 498 32.4 2-yl)-2-ethoxy-1-naphthamide 329 (E)-N-{5-[(1-naphthylmethyl)amino]-1,3,4-thiadiazol-2-yl}- 387 32.4 3-phenyl-2-propenamide 330 N-(5-{[2-(1H-imidazol-4-yl)ethyl]amino}-1,3,4- 371 32.2 thiadiazol-2-yl-1-benzothiophene-2-carboxamide 331 (E)-N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol- -- 32.1 2-yl}-3-phenyl-2-propenamide 332 N-(5-{[2-(acetylamino)ethyl]amino} -1,3,4-thiadiazol-2- 432 32.0 yl)-2,4,6-triisopropylbenzamide 333 (E)-N-{5-[(3,4-dichlorobenzyl)amino]-1,3,4-thiadiazol-2- 405 31.9 yl}-3-phenyl-2-propenamide 334 2-methoxy-N-{5-[(1-naphthylmethyl)amino]-1,3,4- 391 31.8 thiadiazol-2-yl}benzamide 335 N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4- 429 31.7 thiadiazol-2-yl)-4-cyanobenzamide 336 (E)-N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4- -- 31.6 thiadiazol-2-yl)-9-octadecenamide 337 3-nitro-N-(5-{[2-(2-thienyl)ethyl] amino}-1,3,4- 376 31.6 thiadiazol-2-yl)benzamide 338 tert-butyl 3-({5-[(2,6-dichlorobenzoyl)amino]-1,3,4- 417 31.6 thiadiazol-2-yl}amino)propanoate 339 N-{5-[(2-anilinoethyl)amino]-1,3,4 -thiadiazol-2-yl}-4- 466 31.5 iodobenzamide 340 tert-butyl 3-[(5-{[(1,3-dioxo-1,3-dihydro-2-benzofuran-5- 419 31.5 yl)carbonyl]amino}-1,3,4-thiadiazol-2 -yl)amino]propanoate 341 N-{5-[(2-furylmethyl)amino]-1,3,4-thiadiazol-2-yl}-4- 427 31.3 iodobenzamide 342 (E)-3-phenyl-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]-2- 401 31.2 propenamide 343 N-[5-(1,2,3,4-tetrahydro-1-naphthalenylamino)-1,3,4- 407 31.2 thiadiazol-2-yl]-1-benzothiophene-2-c arboxamide 344 ethyl 4-[(5-(1,2,3,4-tetrahydro-1-naphthalenylamino)-1,3,4- 436 31.1 1,3,4-thiadiazol-2-yl)amino]tetrahydro-1(2H)- pyridinecarboxylate 345 4-cyano-N-[5-(phenethylamino)-1,3,4-thiadiazol-2- 350 30.9 yl]benzamide 346 5-chloro-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4- 378 30.7 thiadiazol-2-yl)pentanamide 347 3-nitro-N-[5-(1,2,3,4-tetrahydro-1-naphthalenylamino)-1,3,4- 396 30.6 thiadiazol-2-yl]benzamide 348 N-{5-[(4-fluorobenzyl)amino]-1,3,4-thiadiazol-2-yl}-2- 359 30.4 methoxybenzamide 349 N-{5-[(2-furylmethyl)amino]-1,3,4-thiadiazol-2-yl}-1- 357 30.3 benzothiophene-2-carboxamide 350 N-{5-[(3,4-dichlorobenzyl)amino]-1 ,3,4-thiadiazol-2- 414 30.3 yl}-5-nitro-2-furamide 351 4-bromo-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4- 444 30.3 thiadiazol-2-yl)benzamide 352 (E)-3-(2-chlorophenyl)-N-[5-[(4-pyridinylmethyl)amino]-1,3,4- 372 30.2 thiadiazol-2-yl}-2-propenamide 353 (E)-3-(2-chlorophenyl)-N-[5-(cyclopropylamino)-1,3,4- 321 30.2 thiadiazol-2-yl]-2-propenamide 354 5-chloro-N-[5-(phenethylamino)-1,3 ,4-thiadiazol-2-yl] 339 29.9 pentanamide 355 N-[5-(2,3-dihydro-1H-inden-1-ylamino)-1,3,4-thiadiazol-2- 382 29.8 yl]-3-nitrobenzamide 356 4-methyl-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2- 367 29.6 yl}benzamide 357 (E)-3-(2-chlorophenyl)-N-{5-[(4-phenylbutyl)amino]-1,3,4- -- 29.4 thiadiazol-2-yl}-2-propenamide 358 N-{5-[(1,3-benzodioxol-5-ylmethyl) amino]-1,3,4- 481 29.3 thiadiazol-2-yl}-2,4,6-triisopropylbenzamide 359 4-methyl-N-[5-(phenethylamino)-1,3,4-thiadiazol-2- 339 29.1 yl]benzamide 360 (E)-N-{5-[(cyclohexylmethyl)amino]-1,3,4-thiadiazol-2- 343 29.0 yl}-3-phenyl-2-propenamide 361 N-{5-[(4-fluorobenzyl)amino]-1,3,4-thiadiazol-2-yl}-1- 385 28.8 benzothiophene-2-carboxamide 362 3,5-difluoro-N-{5-[(1-naphthylmeth yl)amino]-1,3,4- 397 28.8 thiadiazol-2-yl}benzamide 363 2,4-difluoro-N-{5-[(1-naphthylmethyl)amino]-1,3,4- 397 28.8 thiadiazol-2-yl}benzamide 364 4-cyano-N-{5-[(cyclohexylmethyl)amino]-1,3,4- 342 28.7 thiadiazol-2-yl}benzamide 365 4-cyano-N-{5-[(2-thienylmethyl)amino]-1,3,4- 342 28.7 thiadiazol-2-yl}benzamide 366 N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4- 434 28.6 thiadiazol-2-yl)-2-methoxybenzamide 367 N-{5-[(1-benzyl-4-piperidinyl)amino]-1,3,4- 520 28.6 thiadiazol-2-yl}-4-iodobenzamide 368 ethyl 4-({5-[(1-benzothiophen-2-ylcarbonyl)amino]- 432 28.5 1,3,4-thiadiazol-2-yl}amino)tetrahydr o-1(2H)- pyridinecarboxylate 369 2,6-dichloro-N-[5-(cycloheptylamino)-1,3,4- 385 28.3 thiadiazol-2-yl]benzamide 370 2,6-dichloro-N-(5-{[2-(1-pyrrolidinyl)ethyl]amino}-1,3,4- 386 28.3 thiadiazol-2-yl)benzamide 371 4-{[(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]amino}-1,3,4- 428 28.1 thiadiazol-2-yl)amino]carbonyl}benzen esulfonyl fluoride 372 N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4- 391 28.1 thiadiazol-2-yl}-3,5-difluorobenzamide 373 3,5-difluoro-N-{5-[(4-phenylbutyl)amino]-1,3,4- 389 28.1 thiadiazol-2-yl}benzamide 374 (E)-3-(2-chlorophenyl)-N-[5-(1,2,3,4-tetrahydro-1- 411 28.1 naphthalenylamino)-1,3,4-thiadiazol-2 -yl]-2-propenamide 375 3,4-dichloro-N-[5-(undecylamino)-1,3,4-thiadiazol-2- 443 27.9 yl]benzamide 376 N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}-4- 483 27.9 (trifluoromethyl)benzamide 377 2,6-dichloro-N-[5-(phenethylamino)-1,3,4-thiadiazol-2- 393 27.8 yl]benzamide 378 (E)-N-(5-{[3-(1H-imidazol-1-yl)propyl]amino}-1,3,4- 489 27.8 thiadiazol-2-yl)-9-octadecenamide 379 (E)-N-{5-[(2-anilinoethyl)amino]-1 ,3,4-thiadiazol-2- 366 27.5 yl}-3-phenyl-2-propenamide 380 N-{5-[(cyclohexylmethyl)amino]-1,3,4-thiadiazol-2- 352 27.5 yl}-5-nitro-2-furamide 381 2,4,6-triisopropyl-N-(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]- 472 27.4 amino}-1,3,4-thiadiazol-2-yl)benzamide 382 5-chloro-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2- 367 27.3 yl}pentanamide 383 N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2- 445 27.3 yl}-2-methoxybenzamide 384 3,4-dichloro-N-{5-[(cyclohexylmethyl)amino]-1,3,4- 385 27.2 thiadiazol-2-yl}benzamide 385 4-bromo-N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2- -- 27.2 yl}benzamide 386 4-bromo-N-{5-[(3,3-diphenylpropyl)amino]-1,3,4- -- 26.9 thiadiazol-2-yl}benzamide 387 N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4- 390 26.8 thiadiazol-2-yl)-2-methoxybenzamide 388 tert-butyl 3-({5-[(2,4,6-triisopropylbenzoyl)amino]-1,3,4- 475 26.6 thiadiazol-2-yl}amino)propanoate 389 N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}- 393 26.5 amino)-1,3,4-thiadiazol-2-yl]-3,5-dif luorobenzamide 390 N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4- 418 26.3 thiadiazol-2-yl)-5-chloropentanamide 391 (E)-N-(5-{[2-(1H-imidazol-4-yl)ethyl]amino}-1,3,4- 475 26.2 thiadiazol-2-yl)-9-octadecenamide 392 2,6-dichloro-N-[5-(neopentylamino) -1,3,4-thiadiazol-2- 359 26.2 yl]benzamide 393 N-{5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2-yl}-4- 354 26.1 methylbenzamide 394 N-{5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2-yl}-2- 370 26.0 methoxybenzamide 395 4-methyl-N-(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]amino}- 360 25.9 1,3,4-thiadiazol-2-yl)benzamide 396 2,4,6-triisopropyl-N-(5-{[2-(2-thi enyl)ethyl]amino}-1,3,4- 457 25.9 thiadiazol-2-yl)benzamide 397 (E)-3-(2-chlorophenyl)-N-(5-{[2-(1-pyrrolidinyl)ethyl]- 378 25.9 amino}-1,3,4-thiadiazol-2-yl)-2-prope namide 398 N-(5-{[4-(aminosulfonyl)benzyl]amino}-1,3,4- 458 25.9 thiadiazol-2-yl)-4-(trifluoromethyl)benzamide 399 2,4,6-triisopropyl-N-{5-[(3-pyridinylmethyl)amino]-1,3,4- 438 25.8 thiadiazol-2-yl}benzamide 400 (E)-N-(5-{[2-(acetylamino)ethyl]amino}-1,3,4-thiadiazol-2- 332 25.8 yl)-3-phenyl-2-propenamide 401 N-{5-[(4-fluorobenzyl)amino]-1,3,4-thiadiazol-2-yl}-2,4,6- 455 25.5 triisopropylbenzamide 402 4-iodo-N-{5-[(1-naphthylmethyl)amino]-1,3,4- -- 25.5 thiadiazol-2-yl}benzamide 403 N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}- -- 25.3 amino)-1,3,4-thiadiazol-2-yl]-1-benzo thiophene-2-carboxamide 404 N-[5-(2,3-dihydro-1H-inden-1-ylamino)-1,3,4-thiadiazol-2- 372 25.2 yl]-5-nitro-2-furamide 405 N-{5-[(tetrahydro-2-furanylmethyl)amino]-1,3,4- 361 25.0 thiadiazol-2-yl}-1-benzothiophene-2-carboxamide 406 N-(5-{[2-(ethylsulfanyl)ethyl]amino}-1,3,4-thiadiazol-2- 377 25.0 yl)-4-(trifluoromethyl)benzamide 407 tert-butyl 3-[(5-{[4-(trifluoromet hyl)benzoyl]amino}-1,3,4- 417 25.0 thiadiazol-2-yl)amino]propanoate 408 N-{5-[(2-anilinoethyl)amino]-1,3,4 -thiadiazol-2-yl}-3,4- 408 24.9 dichlorobenzamide 409 N-{5-[(cyclohexylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2,4,6- 443 24.9 triisopropylbenzamide 410 2,6-dichloro-N-[5-(undecylamino)-1,3,4-thiadiazol-2- 443 24.9 yl]benzamide 411 3-nitro-N-[5-(phenethylamino)-1,3,4-thiadiazol-2- 370 24.8 yl]benzamide 412 N-(5-{[2-(acetylamino)ethyl]amino}-1,3,4-thiadiazol-2- 362 24.7 yl)-1-benzothiophene-2-carboxamide 413 3-nitro-N-{5-[(4-phenylbutyl)amino ]-1,3,4-thiadiazol-2- 398 24.7 yl}benzamide 414 N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4- 385 24.7 thiadiazol-2-yl}-2-methoxybenzamide 415 4-iodo-N-[5-(phenethylamino)-1,3,4-thiadiazol-2-yl]benzamide 451 24.6 416 N-{5-[(3,4-dichlorobenzyl)amino]-1,3,4-thiadiazol-2-yl}-2,4- 415 24.5 difluorobenzamide 417 3,4-dichloro-N-{5-[(3-pyridinylmethyl)amino]-1,3,4- 380 24.4 thiadiazol-2-yl}benzamide 418 3,4-dichloro-N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2- 385 24.4 yl]benzamide 419 4-bromo-N-(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]amino}- 426 24.3 1,3,4-thiadiazol-2-yl)benzamide 420 tert-butyl 3-({5-[(3,4-dichloroben zoyl)amino]-1,3,4- 417 24.1 thiadiazol-2-yl}amino)propanoate 421 (E)-3-phenyl-N-{5-[(3-pyridinylmethyl)amino]-1,3,4- 338 24.0 thiadiazol-2-yl}-2-propenamide 422 (E)-3-(2-chlorophenyl)-N-(5-{[3-(4 -methylpiperazino)- 421 24.0 propyl]amino}-1,3,4-thiadiazol-2-yl)-2-propenamide 423 2,4-difluoro-N-{5-[(4-fluorobenzyl)amino]-1,3,4- 365 23.8 thiadiazol-2-yl}benzamide 424 2,4,6-triisopropyl-N-{5-[(2-thienylmethyl)amino]-1,3,4- 443 23.6 thiadiazol-2-yl}benzamide 425 4-iodo-N-{5-[(2-thienylmethyl)amino]-1,3,4-thiadiazol-2- 443 23.5 yl}benzamide 426 tert-butyl 3-[(5-{[(E)-3-(2-chlorophenyl)-2-propenoyl]- 409 23.5 amino}-1,3,4-thiadiazol-2-yl)amino]pr opanoate 427 2,4-difluoro-N-(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]- 382 23.4 amino}-1,3,4-thiadiazol-2-yl)benzamid e 428 2-methoxy-N-[5-(1,2,3,4-tetrahydro-1-naphthalenylamino)- 381 23.3 1,3,4-thiadiazol-2-yl]benzamide 429 2-methoxy-N-{5-[(4-phenylbutyl)ami no]-1,3,4-thiadiazol-2- 383 23.2 yl}benzamide 430 4-iodo-N-(5-{[2-(2-thienyl)ethyl]amino}-1,3,4-thiadiazol-2- 457 23.1 yl)benzamide 431 N-{5-[(cyclohexylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2- 411 23.1 ethoxy-1-naphthamide 432 (E)-3-phenyl-N-(5-{[2-(1-pyrrolidinyl)ethyl]amino}-1,3,4- 344 23.0 thiadiazol-2-yl)-2-propenamide 433 N-{5-[(cyclohexylmethyl)amino]-1,3 ,4-thiadiazol-2-yl}-2,4- 353 22.9 difluorobenzamide 434 N-{5-[(2-anilioethyl)amino]-1,3,4-thiadiazol-2-yl}-4- 420 22.8 bromobenzamide 435 N-{5-[(2-cyanoethyl)amino]-1,3,4-thiadiazol-2-yl}-2,4,6- 400 22.8 triisopropylbenzamide 436 N-{5-[(3,4-dimethoxybenzyl)amino]-1,3,4-thiadiazol-2- 416 22.8 yl}-3-nitrobenzamide 437 3,5-difluoro-N-[5-(phenethylamino)-1,3,4-thiadiazol-2- 361 22.7 yl]benzamide 438 N-{5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2-yl}-2,6- 408 22.6 dichlorobenzamide 439 (E)-3-(2-chlorophenyl)-N-{5-[(cyclohexylmethyl)amino]- 377 22.5 1,3,4-thiadiazol-2-yl}-2-propenamide 440 N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]- 483 22.5 methyl}amino)-1,3,4-thiadiazol-2-yl]- 2,4,6- triisopropylbenzamide 441 2,4,6-triisopropyl-N-[5-(undecylamino)-1,3,4- 501 22.5 thiadiazol-2-yl]benzamide 442 N-{5-[(2-furylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2,4,6- 427 22.3 triisopropylbenzamide 443 (E)-3-(2-chlorophenyl)-N-{5-[(1-naphthylmethyl)amino]-1,3,4- -- 22.1 thiadiazol-2-yl]-2propenamide 444 N-(5-{[2-(dimethylamino)ethyl]amino}-1,3,4-thiadiazol-2- 418 21.9 yl)-2,4,6-triisopropylbenzamide 445 2,4-difluoro-N-(5-{]2-(2-thienyl)e thyl]amino]-1,3,4- 367 21.9 thiadiazol-2-yl)benzamide 446 N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4- 472 21.8 thiadiazol-2-yl)-4-(trifluoromethyl)benzamide 447 3,4-dichloro-N-(5-{[2-(ethylsulfanyl)ethyl]amino]- 377 21.6 1,3,4-thiadiazol-2-yl)benzamide 448 2,6-dichloro-N-(5-{[2-(1H-imidazol -4-yl)ethyl]amino}- 383 21.6 1,3,4-thiadiazol-2-yl)benzamide 449 N-{5-[(cyclohexylmethyl)amino]-1,3,4-thiadiazol-2-yl}-4- 331 21.5 methylbenzamide 450 2-ethoxy-N-{5-[(tetrahydro-2-furanylmethyl)amino]-1,3,4- 399 21.4 thiadiazol-2-yl}-1-naphthamide 451 3,5-difluoro-N-{5-[(4-fluorobenzyl )amino]-1,3,4- 365 21.4 thiadiazol-2-yl}benzamide 452 N-{5-[(3,4-dichlorobenzyl)amino]-1,3,4-thiadiazol-2- 409 21.3 yl}-2-methoxybenzamide 453 N-{5-[(2-morpholinoethyl)amino]-1,3,4-thiadiazol-2-yl}-1- 390 21.2 benzothiophene-2-carboxamide 454 N-(5-{[2-(1H-imidazol-4-yl)ethyl]a mino}-1,3,4- 441 21.2 thiadiazol-2-yl)-4-iodobenzamide 455 N-{5-[(1-benzyl-4-piperidinyl)amino]-1,3,4-thiadiazol-2- 472 20.8 yl}-4-bromobenzamide 456 N-{5-[(1-benzyl-4-piperidinyl)amino]-1,3,4-thiadiazol-2- 429 20.8 yl}-5-nitro-2-furamide 457 4-methyl-N-{5-[(1-naphthylmethyl)amino]-1,3,4- 375 20.7 thiadiazol-2-yl}benzamide 458 3,5-difluoro-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4- 400 20.7 thiadiazol-2-yl)benzamide 459 N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4- 481 20.7 thiadiazol-2-yl}-4-iodobenzamide 460 4-[({5-[(1-benzyl-4-piperidinyl)amino]-1,3,4-thiadiazol-2- 476 20.7 yl}amino)carbonyl]benzenesulfonyl fluoride 461 3,4-dichloro-N-{5-[(2-ethylhexyl)amino]-1,3,4-thiadiazol-2- 401 20.6 yl}benzamide 462 N-{5-[(3,4-dichlorobenzyl)amino]-1,3,4-thiadiazol-2-yl}-3- 424 20.5 nitrobenzamide 463 N-(5-{[2-(acetylamino)ethyl]amino}-1,3,4-thiadiazol-2- 400 20.3 yl)-2-ethoxy-1-naphthamide 464 4-cyano-N-{5-[(2-morpholinoethyl)amino]-1,3,4-thiadiazol-2- 359 20.3 yl}benzamide 465 (E)-N-[5-(cyclopropylamino)-1,3,4-thiadiazol-2-yl]-3- 287 20.2 phenyl-2-propenamide 466 N-(5-{[2-(ethylsulfanyl)ethyl]amino}-1,3,4-thiadiazol-2- 365 20.1 yl)-1-benzothiophene-2-carboxamide 467 4-iodo-N-(5-{[2-)4-methylpiperazin o)propyl]amino}- 487 20.1 1,3,4-thiadiazol-2-yl)benzamide 468 3,5-difluoro-N-[5-(1,2,3,4-tetrahydro-1-naphthalenylamino)- 387 20.1 1,3,4-thiadiazol-2-yl]benzamide 469 N-{5-[(2-morpholinoethyl)amino]-1,3,4-thiadiazol-2- 379 20.1 yl}-3-nitrobenzamide 470 N-{5-[(cyclopropylmethyl)amino]-1,3,4-thiadiazol-2 401 20.0 yl}-4-iodobenzamide 471 N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4- 380 20.0 thiadiazol-2-yl}-4-cyanobenzamide 472 4-({[5-(phenethylamino)-1,3,4-thiadiazol-2-yl]amino}- 407 20.0 carbonyl)benzenesulfonyl fluoride__________________________________________________________________________
Claims
  • 1. A compound of formula I ##STR16## or pharmaceutically acceptable salts thereof wherein: Y is
  • a) --NHR.sub.1, or ##STR17## X is a) --O--,
  • b) --S(.dbd.O).sub.h --,
  • c) --CH.sub.2 --, or
  • d) --NR.sub.2 --;
  • R.sub.1 is
  • a) C.sub.4-12 alkyl,
  • b) --(CH.sub.2).sub.i -C.sub.3-7 cycloalkyl,
  • c) 6,6-dimethylbicyclo[3.1.1]-2-heptyl,
  • d) --(CH.sub.2).sub.j -M,
  • e) --(CH.sub.2).sub.j -W,
  • f) --(CH.sub.2).sub.k aryl, wherein aryl may be substituted with one to three R.sub.3,
  • g) --(CH.sub.2).sub.k -het, wherein het may be substituted with one to three R.sub.3, or
  • h) --(CH.sub.2).sub.k -Q, wherein Q may be substituted with one to three R.sub.3 ;
  • R.sub.2 is
  • a) H,
  • b) C.sub.1-4 alkyl,
  • c) --C(.dbd.O)C.sub.1-4 alkyl,
  • d) --S(.dbd.O)C.sub.1-4 alkyl,
  • e) --CO.sub.2 C.sub.1-4 alkyl, or
  • f) --CO.sub.2 CH.sub.2 phenyl;
  • R.sub.3 is
  • a) halo,
  • b) C.sub.1-4 alkyl,
  • c) C.sub.1-4 alkoxy,
  • d) benzyl,
  • e) --CN,
  • f) --SO.sub.2 F,
  • g) --SO.sub.2 NH.sub.2,
  • h) --CF.sub.3,
  • i) --NO.sub.2,
  • j) --OCH.sub.2 O--,
  • k) --CO.sub.2 (C.sub.1-4 alkyl),
  • l) --C(.dbd.O)C.sub.1-4 alkyl,
  • m) --C(.dbd.O)NH.sub.2,
  • n) --NHCO.sub.2 (C.sub.1-4 alkyl), or
  • o) --C(.dbd.O)--O--C(.dbd.O)--;
  • M is
  • a) --CN,
  • b) halo,
  • c) --CO.sub.2 C.sub.1-4 alkyl,
  • d) --CH(phenyl).sub.2, ##STR18## W is a) --OR.sub.4,
  • b) --SR.sub.4,
  • c) --NHR.sub.5, or
  • d) --NR.sub.6 R.sub.7 ;
  • R.sub.4 is
  • a) C.sub.1-4 alkyl,
  • b) C.sub.3-7 cycloalkyl, or
  • c) aryl;
  • R.sub.5 is
  • a) C.sub.1-4 alkyl,
  • b) C.sub.3-7 cycloalkyl,
  • c) aryl, or
  • d) --C(.dbd.O)C.sub.1-4 alkyl;
  • R.sub.6 and R.sub.7 are independently
  • a) C.sub.1-4 alkyl, or
  • b) R.sub.6 and R.sub.7 together with nitrogen form azetidinyl, pyrrolidinyl, piperdinyl, piperazinyl, 4-methyl-1-piperazinyl, hydantoin, 4-morpholinyl, thiomorpholinyl, or 2-oxo-1-pyrrolidinyl;
  • R.sub.1 is
  • a) C.sub.1-18 alkyl,
  • b) C.sub.2-18 alkenyl,
  • c) C.sub.2-18 alkynyl,
  • d) C.sub.2-6 alkyl substituted with one to three halo, C.sub.1-3 alkoxy, --OH, --SH, or --CO.sub.2 H,
  • e) C.sub.2-6 alkenyl substituted with aryl, wherein the aryl may be in turn substituted with one to three R.sub.2,
  • f) --(CH.sub.2).sub.i aryl, wherein aryl may be substituted with one to three R.sub.3,
  • g) --(CH.sub.2).sub.i -Q, wherein Q may be substituted with one to three R.sub.3, or
  • h) --(CH.sub.2).sub.i -U, wherein U may be substituted with one to three R.sub.3 ; aryl is phenyl or naphthyl;
  • het is
  • a) furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl,
  • b) pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, pyranyl,
  • c) indazolyl, benzothiazolyl, benzoimidazolyl, benzofuryl, isobenzofuryl, benzothiazole, benzoisoxazole, benzothienyl, indolyl, isoindolyl, or
  • d) quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, phthalazinyl or cinnolinyl;
  • U is
  • a) furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl,
  • b) pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, pyranyl, or
  • c) indazolyl, benzothiazolyl, benzoimidazolyl, benzofuryl, isobenzofuryl, benzothiazole, benzoisoxazole, benzothienyl, indolyl, isoindolyl;
  • Q is
  • a) 2-, 3-, or 4-piperidinyl,
  • b) 1-, or 2-pyrrolidinyl,
  • wherein the nitrogen atom in a) and b) may be substituted with C.sub.1-4 alkyl, phenyl, benzyl, or --C(.dbd.O)C.sub.1-4 alkyl,
  • c) morpholinyl,
  • d) thiomorpholinyl,
  • e) dioxolanyl,
  • f) imidazolidinyl,
  • g) oxathiolanyl,
  • h) oxazolidinyl,
  • i) tetrahydrofuryl, or
  • j) 2-oxo-1-pyrrolidinyl.
  • h is 0, 1, or 2;
  • i is 0, 1, 2, 3, or 4;
  • j is 2, 3, or 4;
  • k is 0, 1, 2, 3, 4, 5, or 6;
  • and with the following provisos:
  • a) where R.sub.3 is phenyl or 4-methoxyphenyl, R.sub.1 is other than phenyl, 4-methoxyphenyl, or 4-chlorophenyl;
  • b) where R.sub.3 is --CH.sub.2 phenyl, R.sub.1 is other than phenyl or --CH.sub.2 phenyl;
  • c) where R.sub.3 is H, substituted or unsubstituted alkyl or phenyl, R.sub.1 is other than unsubstituted alkyl or phenyl.
  • 2. A compound of claim 1 wherein X is
  • a) --O--, or
  • b) --NR.sub.2 --;
  • R.sub.2 is
  • a) H,
  • b) --CO.sub.2 C.sub.1-4 alkyl, or
  • c) --CO.sub.2 CH.sub.2 phenyl.
  • 3. A compound of claim 1 wherein het is furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, isoxazolyl, pyridyl, benzothienyl, or indolyl.
  • 4. A compound of claim 1 wherein Q is 1-methyl-2-pyrrolidinyl, 1-methyl-4-piperidinyl, 1-ethylcarboxylate-4-piperidinyl, 1-benzyl-4-piperidinyl, or tetrahydrofuryl.
  • 5. A compound of claim 1 wherein R.sub.3 is
  • a) chloro,
  • b) fluoro,
  • c) methyl,
  • d) methoxy,
  • e) ethoxy,
  • f) --CN,
  • g) --SO.sub.2 NH.sub.2,
  • h) --NO.sub.2,
  • i) --OCH.sub.2 O--, or
  • j) --C(.dbd.O)--O--C(.dbd.O)--.
  • 6. A compound of claim 1 wherein Rx is
  • a) C.sub.2-18 alkenyl,
  • b) C.sub.2-6 alkyl substituted with halo, or --CO.sub.2 H,
  • c) C.sub.2-6 alkenyl substituted with aryl, wherein the aryl may be in turn substituted with one to three halo,
  • d) --(CH.sub.2).sub.i aryl, wherein aryl may be substituted with one to three R.sub.3, or
  • e) --(CH.sub.2).sub.i -U, wherein het may be substituted with one to three R.sub.3 ;
  • Y is --NHR.sub.1 ; aryl, U, R.sub.1 and i are the same as defined in claim 1; and R.sub.3 is chloro, fluoro, methyl, methoxy, ethoxy, --CN, --SO.sub.2 NH.sub.2, --NO.sub.2, --OCH.sub.2 O--, or --C(.dbd.O)--O--C(.dbd.O)--.
  • 7. A compound of claim 1 which is
  • 1) 2-methoxy-N-[5-(phenethylamino)-1,3,4-thiadiazol-2-yl]benzamide,
  • 2) 4-methyl-N-[5-(phenethylamino)-1,3,4-thiadiazol-2-yl]benzamide,
  • 3) 5-chloro-N-[5-(phenethylamino)-1,3,4-thiadiazol-2-yl]pentanamide,
  • 4) 4-cyano-N-[5-(phenethylamino)-1,3,4-thiadiazol-2-yl]benzamide,
  • 5) 3-nitro-N-[5-(phenethylamino)-1,3,4-thiadiazol-2-yl]benzamide,
  • 6) 3,5-difluoro-N-[5-(phenethylamino)-1,3,4-thiadiazol-2-yl]benzamide,
  • 7) (E)-3-(2-chlorophenyl)-N-[5-(phenethylamino)-1,3,4-thiadiazol-2-yl]-2-propenamide,
  • 8) 2-ethoxy-N-[5-(phenethylamino)-1,3,4-thiadiazol-2-yl]-1-naphthamide,
  • 9) (E)-N-[5-(phenethylamino)-1,3,4-thiadiazol-2-yl]-9-octadecenamide,
  • 10) 2,6-dichloro-N-[5-(phenethylamino)-1,3,4-thiadiazol-2-yl]benzamide,
  • 11) 3,4-dichloro-N-[5-(phenethylamino)-1,3,4-thiadiazol-2-yl]benzamide,
  • 12) (E)-N-[5-(phenethylamino)-1,3,4-thiadiazol-2-yl]-3-phenyl-2-propenamide,
  • 13) 4-iodo-N-[5-(phenethylamino)-1,3,4-thiadiazol-2-yl]benzamide,
  • 14) 1,3-dioxo-N-[5-(phenethylamino)-1,3,4-thiadiazol-2-yl]-1,3-dihydro-2-benzofuran-5-carboxamide,
  • 15) 4-({[5-(phenethylamino)-1,3,4-thiadiazol-2-yl]amino}carbonyl)benzenesulfonyl fluoride,
  • 16) 5-nitro-N-[5-(phenethylamino)-1,3,4-thiadiazol-2-yl]-2-furamide,
  • 17) (E)-3-(2-chlorophenyl)-N-{5-[(2-furylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2-propenamide,
  • 18) 2-ethoxy-N-{5-[(2-furylmethyl)amino]-1,3,4-thiadiazol-2-yl}-1-naphthamide,
  • 19) (E)-N-{5-[(2-furylmethyl)amino]-1,3,4-thiadiazol-2-yl}-9-octadecenamide,
  • 20) 2,6-dichloro-N-{5-[(2-furylmethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 21) 3,4-dichloro-N-{5-[(2-furylmethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 22) N-{5-[(2-furylmethyl)amino]-1,3,4-thiadiazol-2-yl}-4-iodobenzamide,
  • 23) N-{5-[(2-furylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2,4,6-triisopropylbenzamide,
  • 24) N-{5-[(2-furylmethyl)amino]-1,3,4-thiadiazol-2-yl}-1-benzothiophene-2-carboxamide,
  • 25) 2,4-difluoro-N-(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]amino}-1,3,4-thiadiazol-2-yl)benzamide,
  • 26) 4-bromo-N-(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]amino}-1,3,4-thiadiazol-2-yl)benzamide,
  • 27) 4-methyl-N-(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]amino}-1,3,4-thiadiazol-2-yl)benzamide,
  • 28) 5-chloro-N-(5-[3-(2-oxo-1-pyrrolidinyl)propyl]amino}-1,3,4-thiadiazol-2-yl)pentanamide,
  • 29) 4-cyano-N-(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]amino}-1,3,4-thiadiazol-2-yl)benzamide,
  • 30) 3-nitro-N-(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]amino}-1,3,4-thiadiazol-2-yl)benzamide,
  • 31) 3,5-difluoro-N-(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]amino}-1,3,4-thiadiazol-2-yl)benzamide,
  • 32) (E)-3-(2-chlorophenyl)-N-(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]amino}-1,3,4-thiadiazol-2-yl)-2-propenamide,
  • 33) 3,4-dichloro-N-(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]amino}-1,3,4-thiadiazol-2-yl)benzamide,
  • 34) (E)-N-(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]amino}-1,3,4-thiadiazol-2-yl)-3-phenyl-2-propenamide,
  • 35) 4-iodo-N-(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]amino}-1,3,4-thiadiazol-2-yl)benzamide,
  • 36) 1,3-dioxo-N-(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]amino}-1,3,4-thiadiazol-2-yl)-1,3-dihydro-2-benzofuran-5-carboxamide,
  • 37) 4-{[(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]amino}-1,3,4-thiadiazol-2-yl)amino]carbonyl}benzenesulfonyl fluoride,
  • 38) 2,4,6-triisopropyl-N-(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]amino}-1,3,4-thiadiazol-2-yl)benzamide,
  • 39) 5-nitro-N-(5-{[3-(2-oxo-1-pyrrolidinyl)propyl]amino}-1,3,4-thiadiazol-2-yl)-2-furamide,
  • 40) N-(5-[3-(2-oxo-1-pyrrolidinyl)propyl]amino}-1,3,4-thiadiazol-2-yl)-1-benzothiophene-2-carboxamide,
  • 41) (E)-3-(2-chlorophenyl)-N-{5-[(2-pyridinylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2-propenamide,
  • 42) 2-ethoxy-N-{5-[(2-pyridinylmethyl)amino]-1,3,4-thiadiazol-2-yl-1-naphthamide,
  • 43) (E)-N-{5-[(2-pyridinylmethyl)amino]-1,3,4-thiadiazol-2-yl}-9-octadecenamide,
  • 44) 2,6-dichloro-N-{5-[(2-pyridinylmethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 45) (E)-3-phenyl-N-{5-[(2-pyridinylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2-propenamide,
  • 46) N-{5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2-yl}-2-methoxybenzamide,
  • 47) N-{5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2-yl}-4-bromobenzamide,
  • 48) N-{5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2-yl}-4-methylbenzamide,
  • 49) N-{5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2-yl}-3-nitrobenzamide,
  • 50) (E)-N-{5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2-yl}-3-(2-chlorophenyl)-2-propenamide,
  • 51) N-{5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2-yl}-2-ethoxy-1-naphthamide
  • 52) (E)-N-{5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2-yl}-9-octadecenamide,
  • 53) N-{5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2-yl}-2,6-dichlorobenzamide,
  • 54) N-{5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2-yl}-3,4-dichlorobenzamide,
  • 55) (E)-N-{5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2-yl}-3-phenyl-2-propenamide,
  • 56) N-{5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2-yl}-4-iodobenzamide,
  • 57) N-{5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide,
  • 58) 4-[({5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2-yl}amino)carbonyl]benzenesulfonyl fluoride,
  • 59) N-{5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2-yl}-2,4,6-triisopropylbenzamide
  • 60) N-{5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2-yl}-5-nitro-2-furamide,
  • 61) N-{5-[(2-anilinoethyl)amino]-1,3,4-thiadiazol-2-yl}-1-benzothiophene-2-carboxamide,
  • 62) N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-2-methoxybenzamide,
  • 63) 4-bromo-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)benzamide,
  • 64) 5-chloro-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)pentanamide,
  • 65) 4-cyano-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)benzamide,
  • 66) N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-3-nitrobenzamide,
  • 67) 3,5-difluoro-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)benzamide,
  • 68) (E)-3-(2-chlorophenyl)-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-2-propenamide,
  • 69) 2-ethoxy-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-1-naphthamide,
  • 70) (E)-N-(5-[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-9-octadecenamide,
  • 71) 2,6-dichloro-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)benzamide,
  • 72) 3,4-dichloro-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)benzamide,
  • 73) N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-4(trifluoromethyl)benzamide,
  • 74) (E)-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-3-phenyl-2-propenamide,
  • 75) N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-4-iodobenzamide,
  • 76) N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide,
  • 77) 4-[(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)amino]carbonyl}benzenesulfonyl fluoride,
  • 78) N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-2,4,6-triisopropylbenzamide,
  • 79) N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-5-nitro-2-furamide,
  • 80) N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-1-benzothiophene-2-carboxamide,
  • 81) N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-2-methoxybenzamide,
  • 82) N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-4-methylbenzamide,
  • 83) 5-chloro-N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]pentanamide,
  • 84) 4-cyano-N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]benzamide,
  • 85) N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-3-nitrobenzamide,
  • 86) N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-3,5-difluorobenzamide,
  • 87) (E)-3-(2-chlorophenyl)-N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-2-propenamide,
  • 88) N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-2-ethoxy-1-naphthamide,
  • 89) (E)-N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-9-octadecenamide,
  • 90) 2,6-dichloro-N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]benzamide,
  • 91) 3,4-dichloro-N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]benzamide,
  • 92) (E)-N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-3-phenyl-2-propenamide,
  • 93) N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-4-iodobenzamide,
  • 94) N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide,
  • 95) 4-({[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]amino}carbonyl)benzenesulfonyl fluoride,
  • 96) N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-2,4,6-triisopropylbenzamide, N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-5-nitro-2-furamide,
  • 97) N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-1-benzothiophene-2-carboxamide,
  • 98) N-{5-[(cyclohexylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2,4-difluorobenzamide,
  • 99) N-{5-[(cyclohexylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2-methoxybenzamide,
  • 100) N-{5-[(cyclohexylmethyl)amino]-1,3,4-thiadiazol-2-yl}-4-methylbenzamide,
  • 101) 5-chloro-N-{5-[(cyclohexylmethyl)amino]-1,3,4-thiadiazol-2-yl}pentanamide,
  • 102) 4-cyano-N-{5-[(cyclohexylmethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 103) (E)-3-(2-chlorophenyl)-N-{5-[(cyclohexylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2-propenamide,
  • 104) N-{5-[(cyclohexylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2-ethoxy-1-naphthamide,
  • 105) (E)-N-{5-[(cyclohexylmethyl)amino]-1,3,4-thiadiazol-2-yl}-9-octadecenamide
  • 106) 3,4-dichloro-N-{5-[(cyclohexylmethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 107) (E)-N-{5-[(cyclohexylmethyl)amino]-1,3,4-thiadiazol-2-yl}-3-phenyl-2-propenamide,
  • 108) N-{5-[(cyclohexylmethyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide,
  • 109) N-{5-[(cyclohexylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2,4,6-triisopropyl benzamide,
  • 110) N-{5-[(cyclohexylmethyl)amino]-1,3,4-thiadiazol-2-yl}-5-nitro-2-furamide,
  • 111) N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)-1,3,4-thiadiazol-2-yl]-2-methoxybenzamide,
  • 112) 5-chloro-N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)-1,3,4-thiadiazol-2-yl]pentanamide,
  • 113) 4-cyano-N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)-1,3,4-thiadiazol-2-yl]benzamide,
  • 114) N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)-1,3,4-thiadiazol-2-yl]-3,5-difluorobenzamide,
  • 115) (E)-3-(2-chlorophenyl)-N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)-1,3,4-thiadiazol-2-yl]-2-propenamide,
  • 116) N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)-1,3,4-thiadiazol-2-yl]-2-ethoxy-1-naphthamide,
  • 117) (E)-N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)-1,3,4-thiadiazol-2-yl]-9-octadecenamide,
  • 118) N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)-1,3,4-thiadiazol-2-yl]-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide,
  • 119) N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)-1,3,4-thiadiazol-2-yl]-2,4,6-triisopropylbenzamide,
  • 120) N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)-1,3,4-thiadiazol-2-yl]-5-nitro-2-furamide,
  • 121) N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)-1,3,4-thiadiazol-2-yl]-1-benzothiophene-2-carboxamide,
  • 122) (E)-3-(2-chlorophenyl)-N-(5-{[2-(1-pyrrolidinyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-2-propenamide,
  • 123) (E)-N-(5-{[2-(1-pyrrolidinyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-9-octadecenamide,
  • 124) 2-6-dichloro-N-(5-{[2-(1-pyrrolidinyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)benzamide,
  • 125) (E)-3-phenyl-N-(5-{[2-(1-pyrrolidinyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-2-propenamide,
  • 126) 2,4,6-triisopropyl-N-(5-{[2-(1-pyrrolidinyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)benzamide,
  • 127) 2-ethoxy-N-{5-[(tetrahydro-2-furanylmethyl)amino]-1,3,4-thiadiazol-2-yl}-1-naphthamide,
  • 128) (E)-N-{5-[(tetrahydro-2-furanylmethyl)amino]-1,3,4-thiadiazol-2-yl}-9-octadecenamide,
  • 129) N-{5-[(tetrahydro-2-furanylmethyl)amino]-1,3,4-thiadiazol-2-yl}-1-benzothiophene-2-carboxamide,
  • 130) (E)-3-(2-chlorophenyl)-N-{5-[(4-pyridinylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2-propenamide,
  • 131) 2,6-dichloro-N-{5-[(4-pyridinylmethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 132) 3,4-dichloro-N-{5-[(4-pyridinylmethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 133) (E)-3-phenyl-N-{5-[(4-pyridinylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2-propenamide,
  • 134) 4-iodo-N-{5-[(4-pyridinylmethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 135) 1,3-dioxo-N-{5-[(4-pyridinylmethyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dihydro-2-benzofuran-5-carboxamide,
  • 136) 2,4,6-triisopropyl-N-{5-[(4-pyridinylmethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 137) N-{5-[(4-pyridinylmethyl)amino]-1,3,4-thiadiazol-2-yl}-1-benzothiophene-2-carboxamide,
  • 138) N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2,4-difluorobenzamide,
  • 139) N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2-methoxybenzamide,
  • 140) N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4-thiadiazol-2-yl}-4-bromobenzamide,
  • 141) N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4-thiadiazol-2-yl}-4-methylbenzamide,
  • 142) N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4-thiadiazol-2-yl}-5-chloropentanamide,
  • 143) N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4-thiadiazol-2-yl}-4-cyanobenzamide,
  • 144) N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4-thiadiazol-2-yl}-3,5-difluorobenzamide,
  • 145) (E)-N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4-thiadiazol-2-yl}-3-(2-chlorophenyl)-2-propenamide,
  • 146) N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2-ethoxy-1-naphthamide,
  • 147) (E)-N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4-thiadiazol-2-yl}-9-octadecenamide,
  • 148) N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2,6-dichlorobenzamide,
  • 149) (E)-N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4-thiadiazol-2-yl}-3-phenyl-2-propenamide,
  • 150) N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4-thiadiazol-2-yl}-4-iodobenzamide,
  • 151) N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide,
  • 152) N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2,4,6-triisopropylbenzamide,
  • 153) N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4-thiadiazol-2-yl}-1-benzothiophene-2-carboxamide,
  • 154) 4-cyano-N-{5-[(2-morpholinoethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 155) N-{5-[(2-morpholinoethyl)amino]-1,3,4-thiadiazol-2-yl}-3-nitrobenzamide,
  • 156) (E)-N-{5-[(2-morpholinoethyl)amino]-1,3,4-thiadiazol-2-yl}-3-phenyl-2-propenamide,
  • 157) N-{5-[(2-morpholinoethyl)amino]-1,3,4-thiadiazol-2-yl}-1-benzothiophene-2-carboxamide,
  • 158) 2,4-difluoro-N-{5-[(1-naphthylmethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 159) 2-methoxy-N-{5-[(1-naphthylmethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 160) 4-methyl-N-{5-[(1-naphthylmethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 161) 5-chloro-N-{5-[(1-naphthylmethyl)amino]-1,3,4-thiadiazol-2-yl}pentanamide,
  • 162) 4-cyano-N-{5-[(1-naphthylmethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 163) N-{5-[(1-naphthylmethyl)amino]-1,3,4-thiadiazol-2-yl}-3-nitrobenzamide,
  • 164) 3,5-difluoro-N-{5-[(1-naphthylmethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 165) (E)-3-(2-chlorophenyl)-N-{5-[(1-naphthylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2-propenamide,
  • 166) 2-ethoxy-N-{5-[(1-naphthylmethyl)amino]-1,3,4-thiadiazol-2-yl}-1-naphthamide,
  • 167) (E)-N-{5-[(1-naphthylmethyl)amino]-1,3,4-thiadiazol-2-yl}-9-octadecenamide
  • 168) 2,6-dichloro-N-{5-[(1-naphthylmethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 169) (E)-N-{5-[(1-naphthylmethyl)amino]-1,3,4-thiadiazol-2-yl}-3-phenyl-2-propenamide,
  • 170) 4-iodo-N-{5-[(1-naphthylmethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 171) N-{5-[(1-naphthylmethyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide,
  • 172) 4-[({5-[(1-naphthylmethyl)amino]-1,3,4-thiadiazol-2-yl}amino)carbonyl]benzenesulfonyl fluoride,
  • 173) 2,4,6-triisopropyl-N-{5-[(1-naphthylmethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 174) N-{5-[(1-naphthylmethyl)amino]-1,3,4-thiadiazol-2-yl}-5-nitro-2-furamide,
  • 175) N-{5-[(1-naphthylmethyl)amino]-1,3,4-thiadiazol-2-yl}-1-benzothiophene-2-carboxamide,
  • 176) 2,4-difluoro-N-{5-[(4-fluorobenzyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 177) N-{5-[(4-fluorobenzyl)amino]-1,3,4-thiadiazol-2-yl}-2-methoxybenzamide,
  • 178) 5-chloro-N-{5-[(4-fluorobenzyl)amino]-1,3,4-thiadiazol-2-yl}pentanamide,
  • 179) 4-cyano-N-{5-[(4-fluorobenzyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 180) N-{5-[(4-fluorobenzyl)amino]-1,3,4-thiadiazol-2-yl}-3-nitrobenzamide,
  • 181) 3,5-difluoro-N-{5-[(4-fluorobenzyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 182) (E)-3-(2-chlorophenyl)-N-{5-[(4-fluorobenzyl)amino]-1,3,4-thiadiazol-2-yl}-2-propenamide,
  • 183) 2-ethoxy-N-{5-[(4-fluorobenzyl)amino]-1,3,4-thiadiazol-2-yl}-1-naphthamide
  • 184) (E)-N-{5-[(4-fluorobenzyl)amino]-1,3,4-thiadiazol-2-yl}-9-octadecenamide,
  • 185) 2,6-dichloro-N-{5-[(4-fluorobenzyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 186) (E)-N-{5-[(4-fluorobenzyl)amino]-1,3,4-thiadiazol-2-yl}-3-phenyl-2-propenamide,
  • 187) N-{5-[(4-fluorobenzyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide,
  • 188) N-{5-[(4-fluorobenzyl)amino]-1,3,4-thiadiazol-2-yl}-2,4,6-triisopropylbenzamide,
  • 189) N-{5-[(4-fluorobenzyl)amino]-1,3,4-thiadiazol-2-yl}-1-benzothiophene-2-carboxamide
  • 190) 2-ethoxy-N-{5-[(3-pyridinylmethyl)amino]-1,3,4-thiadiazol-2-yl}-1-naphthamide,
  • 191) (E)-N-{5-[(3-pyridinylmethyl)amino]-1,3,4-thiadiazol-2-yl}-9-octadecenamide,
  • 192) 2,6-dichloro-N-{5-[(3-pyridinylmethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 193) 3,4-dichloro-N-{5-[(3-pyridinylmethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 194) (E)-3-phenyl-N-{5-[(3-pyridinylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2-propenamide,
  • 195) 2,4,6-triisopropyl-N-{5-[(3-pyridinylmethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 196) N-{5-[(3-pyridinylmethyl)amino]-1,3,4-thiadiazol-2-yl}-1-benzothiophene-2-carboxamide,
  • 197) 2,4,6-triisopropyl-N-{5-[(2-piperidinoethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 198) (E)-N-{5-[(2-ethylhexyl)amino]-1,3,4-thiadiazol-2-yl}-9-octadecenamide,
  • 199) 2,6-dichloro-N-{5-[(2-ethylhexyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 200) 3,4-dichloro-N-{5-[(2-ethylhexyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 201) N-{5-[(2-ethylhexyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide,
  • 202) N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4-thiadiazol-2-yl)-2-methoxybenzamide,
  • 203) N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4-thiadiazol-2-yl)-4-bromobenzamide,
  • 204) N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4-thiadiazol-2-yl)-4-methylbenzamide,
  • 205) N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4-thiadiazol-2-yl)-5-chloropentanamide,
  • 206) N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4-thiadiazol-2-yl)-4-cyanobenzamide,
  • 207) (E)-N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4-thiadiazol-2-yl)-3-(2-chlorophenyl)-2-propenamide,
  • 208) N-(5-{[4-(aminosulfonyl)phenethyl]amino}1,3,4-thiadiazol-2-yl)-2-ethoxy-1-naphthamide,
  • 209) (E)-N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4-thiadiazol-2-yl)-9-octadecenamide,
  • 210) N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4-thiadiazol-2-yl)-2,6-dichlorobenzamide,
  • 211) N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4-thiadiazol-2-yl)-3,4-dichlorobenzamide,
  • 212) N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4-thiadiazol-2-yl)-4-(trifluoromethyl)benzamide,
  • 213) (E)-N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4-thiadiazol-2-yl)-3-phenyl-2-propenamide,
  • 214) N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4-thiadiazol-2-yl)-4-iodobenzamide,
  • 215) N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4-thiadiazol-2-yl)-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide,
  • 216) N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4-thiadiazol-2-yl)-2,4,6-triisopropylbenzamide,
  • 217) N-(5-{[4-(aminosulfonyl)phenethyl]amino}-1,3,4-thiadiazol-2-yl)-1-benzothiophene-2-carboxamide,
  • 218) N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-2,4-difluorobenzamide,
  • 219) N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-2-methoxybenzamide,
  • 220) 4-bromo-N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)benzamide,
  • 221) N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-4-methylbenzamide,
  • 222) 4-cyano-N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)benzamide,
  • 223) N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-3-nitrobenzamide,
  • 224) N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-3,5-difluorobenzamide,
  • 225) (E)-3-(2-chlorophenyl)-N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-2-propenamide,
  • 226) N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-2-ethoxy-1-naphthamide,
  • 227) (E)-N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-9-octadecenamide,
  • 228) 2,6-dichloro-N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)benzamide,
  • 229) 3,4-dichloro-N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)benzamide,
  • 230) N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-4-(trifluoromethyl)benzamide,
  • 231) (E)-N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-3-phenyl-2-propenamide,
  • 232) N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-4-iodobenzamide,
  • 233) N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide,
  • 234) 4-{[(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)amino]carbonyl}benzenesulfonyl fluoride,
  • 235) N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-2,4,6-triisopropylbenzamide,
  • 236) N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-5-nitro-2-furamide,
  • 237) N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-1-benzothiophene-2-carboxamide,
  • 238) N-{5-[(3,4-dichlorobenzyl)amino]-1,3,4-thiadiazol-2-yl}-2,4-difluorobenzamide,
  • 239) N-{5-[(3,4-dichlorobenzyl)amino]-1,3,4-thiadiazol-2-yl}-2-methoxybenzamide
  • 240) 4-cyano-N-{5-[(3,4-dichlorobenzyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 241) N-{5-[(3,4-dichlorobenzyl)amino]-1,3,4-thiadiazol-2-yl}-3-nitrobenzamide,
  • 242) N-{5-[(3,4-dichlorobenzyl)amino]-1,3,4-thiadiazol-2-yl}-2-ethoxy-1-naphthamide,
  • 243) (E)-N-{5-[(3,4-dichlorobenzyl)amino]-1,3,4-thiadiazol-2-yl}-9-octadecenamide,
  • 244) 2,6-dichloro-N-{5-[(3,4-dichlorobenzyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 245) (E)-N-{5-[(3,4-dichlorobenzyl)amino]-1,3,4-thiadiazol-2-yl}-3-phenyl-2-propenamide,
  • 246) N-{5-[(3,4-dichlorobenzyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide,
  • 247) N-{5-[(3,4-dichlorobenzyl)amino]-1,3,4-thiadiazol-2-yl}-5-nitro-2-furamide
  • 248) 4-cyano-N-{5-[(3,4-dimethoxybenzyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 249) N-{5-[(3,4-dimethoxybenzyl)amino]-1,3,4-thiadiazol-2-yl}-3-nitrobenzamide,
  • 250) N-{5-[(3,4-dimethoxybenzyl)amino]-1,3,4-thiadiazol-2-yl}-2-ethoxy-1-naphthamide,
  • 251) (E)-N-{5-[(3,4-dimethoxybenzyl)amino]-1,3,4-thiadiazol-2-yl}-9-octadecenamide,
  • 252) 2,6-dichloro-N-{5-[(3,4-dimethoxybenzyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 253) N-{5-[(3,4-dimethoxybenzyl)amino]-1,3,4-thiadiazol-2-yl}-4-iodobenzamide,
  • 254) N-{5-[(3,4-dimethoxybenzyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide,
  • 255) 2,4-difluoro-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 256) 2-methoxy-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 257) 4-bromo-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 258) 4-methyl-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 259) 5-chloro-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}pentanamide,
  • 260) 4-cyano-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 261) 3-nitro-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 262) 3,5-difluoro-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 263) (E)-3-(2-chlorophenyl)-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}-2-propenamide,
  • 264) 2-ethoxy-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}-1-naphthamide,
  • 265) (E)-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}-9-octadecenamide,
  • 266) 2,6-dichloro-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 267) 3,4-dichloro-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 268) N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}-4-(trifluoromethyl) benzamide,
  • 269) (E)-3-phenyl-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}-2-propenamide,
  • 270) 4-iodo-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 271) 1,3-dioxo-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dihydro-2-benzofuran-5-carboxamide,
  • 272) 4-[({5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}amino)carbonyl]benzenesulfonyl fluoride,
  • 273) 2,4,6-triisopropyl-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 274) 5-nitro-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}-2-furamide,
  • 275) N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}-1-benzothiophene-2-carboxamide,
  • 276) N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}-2,4-difluorobenzamide,
  • 277) N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}-2-methoxybenzamide,
  • 278) 4-bromo-N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 279) 5-chloro-N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}pentanamide
  • 280) 4-cyano-N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 281) N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}-3,5-difluorobenzamide,
  • 282) (E)-3-(2-chlorophenyl)-N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}-2-propenamide,
  • 283) N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}-2-ethoxy-1-naphthamide,
  • 284) (E)-N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}-9-octadecenamide,
  • 285) 2,6-dichloro-N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 286) N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide,
  • 287) 4-[({5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}amino)carbonyl]benzenesulfonyl fluoride,
  • 288) N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}-2,4,6-triisopropyl benzamide,
  • 289) N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}-5-nitro-2-furamide,
  • 290) N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}-1-benzothiophene-2-carboxamide,
  • 291) 2,4-difluoro-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]benzamide,
  • 292) 4-bromo-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]benzamide,
  • 293) 4-methyl-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]benzamide,
  • 294) 5-chloro-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]pentanamide,
  • 295) 4-cyano-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]benzamide,
  • 296) 3-nitro-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]benzamide,
  • 297) 3,5-difluoro-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]benzamide,
  • 298) (E)-3-(2-chlorophenyl)-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]-2-propenamide,
  • 299) 2-ethoxy-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]-1-naphthamide,
  • 300) (E)-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]-9-octadecenamide,
  • 301) 2,6-dichloro-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]benzamide,
  • 302) 3,4-dichloro-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]benzamide,
  • 303) 4-(trifluoromethyl)-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]benzamide,
  • 304) (E)-3-phenyl-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]-2-propenamide,
  • 305) 4-iodo-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]benzamide,
  • 306) 1,3-dioxo-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]-1,3-dihydro-2-benzofuran-5-carboxamide,
  • 307) 4-({[5-(undecylamino)-1,3,4-thiadiazol-2-yl]amino}carbonyl)benzenesulfonyl fluoride,
  • 308) 2,4,6-triisopropyl-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]benzamide,
  • 309) 5-nitro-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]-2-furamide,
  • 310) N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]-1-benzothiophene-2-carboxamide,
  • 311) N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}-2,4-difluorobenzamide,
  • 312) N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}-2-methoxybenzamide
  • 313) 4-bromo-N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl benzamide,
  • 314) 5-chloro-N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}pentanamide,
  • 315) 4-cyano-N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 316) N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}-3-nitrobenzamide,
  • 317) N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}-3,5-difluorobenzamide,
  • 318) (E)-3-(2-chlorophenyl)-N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}-2-propenamide,
  • 319) N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}-2-ethoxy-1-naphthamide,
  • 320) (E)-N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}-9-octadecenamide,
  • 321) 2,6-dichloro-N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 322) N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}-4-(trifluoromethyl) benzamide,
  • 323) (E)-N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}-3-phenyl-2-propenamide,
  • 324) N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}-4-iodobenzamide,
  • 325) N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide,
  • 326) 4-[({5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}amino)carbonyl]benzenesulfonyl fluoride,
  • 327) N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}-2,4,6-triisopropylbenzamide,
  • 328) N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}-5-nitro-2-furamide
  • 329) N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}-1-benzothiophene-2-carboxamide,
  • 330) 2,4-difluoro-N-(5-{[2-(2-thienyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)benzamide,
  • 331) 4-cyano-N-(5-{[2-(2-thienyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)benzamide,
  • 332) 3-nitro-N-(5-{[2-(2-thienyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)benzamide,
  • 333) (E)-3-(2-chlorophenyl)-N-(5-{[2-(2-thienyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-2-propenamide,
  • 334) 2-ethoxy-N-(5-{[2-(2-thienyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-1-naphthamide,
  • 335) (E)-N-(5-{[2-(2-thienyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-9-octadecenamide,
  • 336) 2,6-dichloro-N-(5-{[2-(2-thienyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)benzamide,
  • 337) (E)-3-phenyl-N-(5-{[2-(2-thienyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-2-propenamide,
  • 338) 4-iodo-N-(5-{[2-(2-thienyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)benzamide,
  • 339) 1,3-dioxo-N-(5-{[2-(2-thienyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-1,3-dihydro-2-benzofuran-5-carboxamide,
  • 340) 2,4,6-triisopropyl-N-(5-{[2-(2-thienyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)benzamide,
  • 341) N-(5-{[2-(2-thienyl)ethyl]amino-1,3,4-thiadiazol-2-yl)-1-benzothiophene-2-carboxamide,
  • 342) (E)-N-(5-{[4-(aminosulfonyl)benzyl]amino}-1,3,4-thiadiazol-2-yl)-3-(2-chlorophenyl)-2-propenamide,
  • 343) N-(5-[4-(aminosulfonyl)benzyl]amino}-1,3,4-thiadiazol-2-yl)-2-ethoxy-1-naphthamide,
  • 344) (E)-N-(5-{[4-(aminosulfonyl)benzyl]amino}-1,3,4-thiadiazol-2-yl)-9-octadecenamide,
  • 345) N-(5-{[4-(aminosulfonyl)benzyl]amino}-1,3,4-thiadiazol-2-yl)-2,6-dichlorobenzamide,
  • 346) N-(5-{[4-(aminosulfonyl)benzyl]amino}-1,3,4-thiadiazol-2-yl)-3,4-dichlorobenzamide,
  • 347) N-(5-{[4-(aminosulfonyl)benzyl]amino}-1,3,4-thiadiazol-2-yl)-4-(trifluoromethyl)benzamide,
  • 348) (E)-N-(5-{[4-(aminosulfonyl)benzyl]amino}-1,3,4-thiadiazol-2-yl)-3-phenyl-2-propenamide,
  • 349) N-(5-{[4-(aminosulfonyl)benzyl]amino}-1,3,4-thiadiazol-2-yl)-4-iodobenzamide,
  • 350) N-(5-{[4-(aminosulfonyl)benzyl]amino}-1,3,4-thiadiazol-2-yl)-2,4,6-triisopropylbenzamide,
  • 351) N-(5-{[4-(aminosulfonyl)benzyl]amino}-1,3,4-thiadiazol-2-yl)-1-benzothiophene-2-carboxamide,
  • 352) (E)-3-(2-chlorophenyl)-N-(5-{[3-(4-methylpiperazino)propyl]amino}-1,3,4-thiadiazol-2-yl)-2-propenamide,
  • 353) (E)-N-(5-{[3-(4-methylpiperazino)propyl]amino}-1,3,4-thiadiazol-2-yl)-9-octadecenamide,
  • 354) 4-iodo-N-(5-{[3-(4-methylpiperazino)propyl]amino}-1,3,4-thiadiazol-2-yl)benzamide,
  • 355) (E)-N-{5-[(2-cyanoethyl)amino]-1,3,4-thiadiazol-2-yl}-9-octadecenamide,
  • 356) 2,6-dichloro-N-{5-[(2-cyanoethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 357) N-{5-[(2-cyanoethyl)amino]-1,3,4-thiadiazol-2-yl}-2,4,6-triisopropylbenzamide,
  • 358) 2,4-difluoro-N-(5-{[2-(phenylsulfanyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)benzamide,
  • 359) 4-bromo-N-(5-{[2-(phenylsulfanyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)benzamide,
  • 360) 5-chloro-N-(5-{[2-(phenylsulfanyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)pentanamide,
  • 361) (E)-3-(2-chlorophenyl)-N-(5-{[2-(phenylsulfanyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-2-propenamide,
  • 362) 2-ethoxy-N-(5-{[2-(phenylsulfanyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-1-naphthamide,
  • 363) (E)-N-(5-{[2-(phenylsulfanyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-9-octadecenamide,
  • 364) (E)-3-phenyl-N-(5-{[2-(phenylsulfanyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-2-propenamide,
  • 365) 4-iodo-N-(5-{[2-(phenylsulfanyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)benzamide,
  • 366) 1,3-dioxo-N-(5-{[2-(phenylsulfanyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-1,3-dihydro-2-benzofuran-5-carboxamide,
  • 367) 4-cyano-N-{5-[(2-thienylmethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 368) (E)-3-(2-chlorophenyl)-N-{5-[(2-thienylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2-propenamide,
  • 369) 2-ethoxy-N-{5-[(2-thienylmethyl)amino]-1,3,4-thiadiazol-2-yl}-1-naphthamide,
  • 370) (E)-N-{5-[(2-thienylmethyl)amino]-1,3,4-thiadiazol-2-yl}-9-octadecenamide,
  • 371) 2,6-dichloro-N-{5-[(2-thienylmethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide
  • 372) 4-iodo-N-{5-[(2-thienylmethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 373) 1,3-dioxo-N-{5-[(2-thienylmethyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dihydro-2-benzofuran-5-carboxamide,
  • 374) 2,4,6-triisopropyl-N-{5-[(2-thienylmethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 375) N-{5-[(2-thienylmethyl)amino]-1,3,4-thiadiazol-2-yl}-1-benzothiophene-2-carboxamide,
  • 376) N-(5-{[2-(acetylamino)ethyl]amino}-1,3,4-thiadiazol-2-yl)-2-ethoxy-1-naphthamide,
  • 377) (E)-N-(5-{[2-(acetylamino)ethyl]amino}-1,3,4-thiadiazol-2-yl)-9-octadecenamide,
  • 378) (E)-N-(5-{[2-(acetylamino)ethyl]amino}-1,3,4-thiadiazol-2-yl)-3-phenyl-2-propenamide,
  • 379) N-(5-{[2-(acetylamino)ethyl]amino}-1,3,4-thiadiazol-2-yl)-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide,
  • 380) N-(5-{[2-(acetylamino)ethyl]amino}-1,3,4-thiadiazol-2-yl)-2,4,6-triisopropylbenzamide,
  • 381) N-(5-{[2-(acetylamino)ethyl]amino}-1,3,4-thiadiazol-2-yl)-1-benzothiophene-2-carboxamide,
  • 382) 4-bromo-N-(5-{[3-(1H-imidazol-1-yl)propyl]amino}-1,3,4-thiadiazol-2-yl)benzamide,
  • 383) (E)-3-(2-chlorophenyl)-N-(5-{[3-(1H-imidazol-1-yl)propyl]amino}-1,3,4-thiadiazol-2-yl)-2-propenamide,
  • 384) 2-ethoxy-N-(5-{[3-(1H-imidazol-1-yl)propyl]amino}-1,3,4-thiadiazol-2-yl)-1-naphthamide,
  • 385) (E)-N-(5-{[3-(1H-imidazol-1-yl)propyl]amino}-1,3,4-thiadiazol-2-yl)-9-octadecenamide,
  • 386) 2,6-dichloro-N-(5-{[3-(1H-imidazol-1-yl)propyl]amino}-1,3,4-thiadiazol-2-yl)benzamide,
  • 387) 3,4-dichloro-N-(5-{[3-(1H-imidazol-1-yl)propyl]amino}-1,3,4-thiadiazol-2-yl)benzamide,
  • 388) (E)-N-(5-{[3-(1H-imidazol-1-yl)propyl]amino}-1,3,4-thiadiazol-2-yl)-3-phenyl-2-propenamide,
  • 389) N-(5-{[3-(1H-imidazol-1-yl)propyl]amino}-1,3,4-thiadiazol-2-yl)-4-iodobenzamide,
  • 390) N-(5-{[3-(1H-imidazol-1-yl)propyl]amino}-1,3,4-thiadiazol-2-yl)-2,4,6-triisopropylbenzamide,
  • 391) tert-butyl 3-[(5-{[(E)-3-(2-chlorophenyl)-2-propenoyl]amino}-1,3,4-thiadiazol-2-yl)amino]propanoate,
  • 392) tert-butyl 3-[(5-{[(2-ethoxy-1-naphthyl)carbonyl]amino}-1,3,4-thiadiazol-2-yl)amino]propanoate,
  • 393) tert-butyl 3-({5-[(E)-9-octadecenoylamino]-1,3,4-thiadiazol-2-yl}amino)propanoate,
  • 394) tert-butyl 3-({5-[(2,6-dichlorobenzoyl)amino]-1,3,4-thiadiazol-2-yl}amino)propanoate,
  • 395) tert-butyl 3-({5-[(3,4-dichlorobenzoyl)amino]-1,3,4-thiadiazol-2-yl}amino)propanoate,
  • 396) tert-butyl 3-[(5-{[4-(trifluoromethyl)benzoyl]amino}-1,3,4-thiadiazol-2-yl)amino]propanoate,
  • 397) tert-butyl 3-[(5-1-[(E)-3-phenyl-2-propenoyl]amino}-1,3,4-thiadiazol-2-yl)amino]propanoate,
  • 398) tert-butyl 3-[(5-{[(1,3-dioxo-1,3-dihydro-2-benzofuran-5-yl)carbonyl]amino}-1,3,4-thiadiazol-2-yl)amino]propanoate,
  • 399) tert-butyl 3-({5-[(2,4,6-triisopropylbenzoyl)amino]-1,3,4-thiadiazol-2-yl}amino)propanoate,
  • 400) (E)-3-(2-chlorophenyl)-N-[5-(cyclopropylamino)-1,3,4-thiadiazol-2-yl]-2-propenamide,
  • 401) N-[5-(cyclopropylamino)-1,3,4-thiadiazol-2-yl]-2-ethoxy-1-naphthamide,
  • 402) (E)-N-[5-(cyclopropylamino)-1,3,4-thiadiazol-2-yl]-9-octadecenamide,
  • 403) (E)-N-[5-(cyclopropylamino)-1,3,4-thiadiazol-2-yl]-3-phenyl-2-propenamide,
  • 404) N-[5-(cyclopropylamino)-1,3,4-thiadiazol-2-yl]-1-benzothiophene-2-carboxamide,
  • 405) (E)-3-(2-chlorophenyl)-N-{5-[(cyclopropylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2-propenamide,
  • 406) N-{5-[(cyclopropylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2-ethoxy-1-naphthamide,
  • 407) (E)-N-{5-[(cyclopropylmethyl)amino]-1,3,4-thiadiazol-2-yl}-9-octadecenamide,
  • 408) N-{5-[(cyclopropylmethyl)amino]-1,3,4-thiadiazol-2-yl}-4-iodobenzamide,
  • 409) (E)-3-(2-chlorophenyl)-N-(5-{[2-(1H-imidazol-4-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-2-propenamide,
  • 410) 2-ethoxy-N-(5-{[2-(1H-imidazol-4-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-1-naphthamide,
  • 411) (E)-N-(5-{[2-(1H-imidazol-4-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-9-octadecenamide,
  • 412) 2,6-dichloro-N-(5-{[2-(1H-imidazol-4-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)benzamide,
  • 413) (E)-N-(5-{[2-(1H-imidazol-4-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-3-phenyl-2-propenamide,
  • 414) N-(5-{[2-(1H-imidazol-4-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-4-iodobenzamide,
  • 415) N-(5-{[2-(1H-imidazol-4-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-2,4,6-triisopropylbenzamide,
  • 415) N-(5-{[2-(1H-imidazol-4-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-1-benzothiophene-2-carboxamide,
  • 416) 4-bromo-N-(5-{[2-(ethylsulfanyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)benzamide,
  • 417) (E)-3-(2-chlorophenyl)-N-(5-{[2-(ethylsulfanyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-2-propenamide,
  • 418) 2-ethoxy-N-(5-{[2-(ethylsulfanyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-1-naphthamide,
  • 419) (E)-N-(5-{[2-(ethylsulfanyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-9-octadecenamide,
  • 420) 2,6-dichloro-N-(5-{[2-(ethylsulfanyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)benzamide,
  • 421) 3,4-dichloro-N-(5-{[2-(ethylsulfanyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)benzamide,
  • 422) N-(5-{[2-(ethylsulfanyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-4(trifluoromethyl)benzamide,
  • 423) (E)-N-(5-{[2-(ethylsulfanyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-3-phenyl-2-propenamide,
  • 424) N-(5-{[2-(ethylsulfanyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-4-iodobenzamide,
  • 425) N-(5-{[2-(ethylsulfanyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-1-benzothiophene-2-carboxamide,
  • 426) (E)-3-(2-chlorophenyl)-N-[5-(cyclobutylamino)-1,3,4-thiadiazol-2-yl]-2-propenamide,
  • 427) N-[5-(cyclobutylamino)-1,3,4-thiadiazol-2-yl]-2-ethoxy-1-naphthamide,
  • 428) (E)-N-[5-(cyclobutylamino)-1,3,4-thiadiazol-2-yl]-9-octadecenamide,
  • 429) (E)-N-(5-{[2-(1-methyl-2-pyrrolidinyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-9-octadecenamide,
  • 430) 2,4,6-triisopropyl-N-(5-{[2-(1-methyl-2-pyrrolidinyl)ethyl]amino}-1,3,4-thiadiazol-2-yl)benzamide,
  • 431) N-[5-(2,3-dihydro-1H-inden-1-ylamino)-1,3,4-thiadiazol-2-yl]-3-nitrobenzamide,
  • 432) N-[5-(2,3-dihydro-1H-inden-1-ylamino)-1,3,4-thiadiazol-2-yl]-2-ethoxy-1-naphthamide,
  • 433) (E)-N-[5-(2,3-dihydro-1H-inden-1-ylamino)-1,3,4-thiadiazol-2-yl]-9-octadecenamide,
  • 434) 2,6-dichloro-N-[5-(2,3-dihydro-1H-inden-1-ylamino)-1,3,4-thiadiazol-2-yl]benzamide,
  • 435) N-[5-(2,3-dihydro-1H-inden-1-ylamino)-1,3,4-thiadiazol-2-yl]-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide,
  • 436) N-[5-(2,3-dihydro-1H-inden-1-ylamino)-1,3,4-thiadiazol-2-yl]-5-nitro-2-furamide,
  • 437) (E)-3-(2-chlorophenyl)-N-[5-(neopentylamino)-1,3,4-thiadiazol-2-yl]-2-propenamide,
  • 438) 2-ethoxy-N-[5-(neopentylamino)-1,3,4-thiadiazol-2-yl]-1-naphthamide,
  • 439) 2,6-dichloro-N-[5-(neopentylamino)-1,3,4-thiadiazol-2-yl]benzamide,
  • 440) 2-methoxy-N-[5-(1,2,3,4-tetrahydro-1-naphthalenylamino)-1,3,4-thiadiazol-2-yl]benzamide,
  • 441) 3-nitro-N-[5-(1,2,3,4-tetrahydro-1-naphthalenylamino)-1,3,4-thiadiazol-2-yl]benzamide,
  • 442) 3,5-difluoro-N-[5-(1,2,3,4-tetrahydro-1-naphthalenylamino)-1,3,4-thiadiazol-2-yl]benzamide,
  • 443) (E)-3-(2-chlorophenyl)-N-[5-(1,2,3,4-tetrahydro-1-naphthalenylamino)-1,3,4-thiadiazol-2-yl]-2-propenamide,
  • 444) 2-ethoxy-N-[5-(1,2,3,4-tetrahydro-1-naphthalenylamino)-1,3,4-thiadiazol-2-yl]-1-naphthamide,
  • 445) (E)-N-[5-(1,2,3,4-tetrahydro-1-naphthalenylamino)-1,3,4-thiadiazol-2-yl]-9-octadecenamide,
  • 446) 2,6-dichloro-N-[5-(1,2,3,4-tetrahydro-1-naphthalenylamino)-1,3,4-thiadiazol-2-yl]benzamide,
  • 447) 1,3-dioxo-N-[5-(1,2,3,4-tetrahydro-1-naphthalenylamino)-1,3,4-thiadiazol-2-yl]-1,3-dihydro-2-benzofuran-5-carboxamide,
  • 448) 5-nitro-N-[5-(1,2,3,4-tetrahydro-1-naphthalenylamino)-1,3,4-thiadiazol-2-yl]-2-furamide,
  • 449) N-[5-(1,2,3,4-tetrahydro-1-naphthalenylamino)-1,3,4-thiadiazol-2-yl]-1-benzothiophene-2-carboxamide,
  • 450) ethyl 4-[(5-{[(E)-3-(2-chlorophenyl)-2-propenoyl]amino}-1,3,4-thiadiazol-2-yl)amino]tetrahydro-1(2H)-pyridinecarboxylate,
  • 451) ethyl 4-[(5-{[(2-ethoxy-1-naphthyl)carbonyl]amino}-1,3,4-thiadiazol-2-yl)amino]tetrahydro-1(2H)-pyridinecarboxylate,
  • 452) ethyl 4-({5-[(E)-9-octadecenoylamino]-1,3,4-thiadiazol-2-yl}amino)tetrahydro-1(2H)-pyridinecarboxylate,
  • 453) ethyl 4-({5-[(2,6-dichlorobenzoyl)amino]-1,3,4-thiadiazol-2-yl}amino)tetrahydro-1(2H)-pyridinecarboxylate,
  • 454) ethyl 4-({5-[(1-benzothiophen-2-ylcarbonyl)amino]-1,3,4-thiadiazol-2-yl}amino)tetrahydro-1(2H)-pyridinecarboxylate,
  • 455) N-{5-[(1-benzyl-4-piperidinyl)amino]-1,3,4-thiadiazol-2-yl}-4-bromobenzamide,
  • 456) (E)-N-{5-[(1-benzyl-4-piperidinyl)amino]-1,3,4-thiadiazol-2-yl}-3-(2-chlorophenyl)-2-propenamide,
  • 457) N-{5-[(1-benzyl-4-piperidinyl)amino]-1,3,4-thiadiazol-2-yl}-2-ethoxy-1-naphthamide,
  • 458) (E)-N-{5-[(1-benzyl-4-piperidinyl)amino]-1,3,4-thiadiazol-2-yl}-9-octadecenamide,
  • 459) N-{5-[(1-benzyl-4-piperidinyl)amino]-1,3,4-thiadiazol-2-yl}-2,6-dichlorobenzamide,
  • 460) (E)-N-{5-[(1-benzyl-4-piperidinyl)amino]-1,3,4-thiadiazol-2-yl}-3-phenyl-2-propenamide,
  • 461) N-{5-[(1-benzyl-4-piperidinyl)amino]-1,3,4-thiadiazol-2-yl}-4-iodobenzamide,
  • 462) N-{5-[(1-benzyl-4-piperidinyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide,
  • 463) 4-[({5-[(1-benzyl-4-piperidinyl)amino]-1,3,4-thiadiazol-2- yl}amino)carbonyl]benzenesulfonyl fluoride,
  • 464) N-{5-[(1-benzyl-4-piperidinyl)amino]-1,3,4-thiadiazol-2-yl}-2,4,6-triisopropylbenzamide,
  • 465) N-{5-[(1-benzyl-4-piperidinyl)amino]-1,3,4-thiadiazol-2-yl}-5-nitro-2-furamide,
  • 466) N-{5-[(1-benzyl-4-piperidinyl)amino]-1,3,4-thiadiazol-2-yl}-1-benzothiophene-2-carboxamide,
  • 467) (E)-N-(5-{[2-(dimethylamino)ethyl]amino}-1,3,4-thiadiazol-2-yl)-9-octadecenamide, or
  • 468) N-(5-{[2-(dimethylamino)ethyl]amino}-1,3,4-thiadiazol-2-yl)-2,4,6-triisopropylbenzamide.
  • 8. A compound of claim 1 which is
  • 1) N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-2-ethoxy-1-naphthamide,
  • 2) N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide,
  • 3) N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide,
  • 4) N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide,
  • 5) 1,3-dioxo-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]-1,3-dihydro-2-benzofuran-5-carboxamide,
  • 6) N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)-1,3,4-thiadiazol-2-yl]-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide,
  • 7) 1,3-dioxo-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dihydro-2-benzofuran-5-carboxamide,
  • 8) N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide,
  • 9) (E)-N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-9-octadecenamide,
  • 10) 2-ethoxy-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-1-naphthamide,
  • 11) 2,6-dichloro-N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)benzamide,
  • 12) N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-2-ethoxy-1-naphthamide,
  • 13) N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)-1,3,4-thiadiazol-2-yl]-2-ethoxy-1-naphthamide,
  • 14) (E)-N-(5-{[4-(aminosulfonyl)benzyl]amino}-1,3,4-thiadiazol-2-yl)-9-octadecenamide,
  • 15) N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}-2-ethoxy-1-naphthamide,
  • 16) (E)-N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-3-phenyl-2-propenamide,
  • 17) 2,6-dichloro-N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 18) 2,6-dichloro-N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 19) (E)-N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4-thiadiazol-2-yl}-9-octadecenamide,
  • 20) N-(5-{[4-(aminosulfonyl)benzyl]amino}-1,3,4-thiadiazol-2-yl)-2,6-dichlorobenzamide,
  • 21) 2,6-dichloro-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)benzamide,
  • 22) 4-cyano-N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}benzamide,
  • 23) N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide,
  • 24) 4-cyano-N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)benzamide,
  • 25) N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-5-nitro-2-furamide,
  • 26) 2,6-dichloro-N-[5-{[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)-1,3,4-thiadiazol-2-yl]benzamide,
  • 27) 4-cyano-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)benzamide,
  • 28) N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide,
  • 29) N-{5-[(1,3-benzodioxol-5-ylmethyl)amino]-1,3,4-thiadiazol-2-yl}-2,6dichlorobenzamide,
  • 30) N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}-2-methoxybenzamide,
  • 31) (E)-N-(5-{[4-(aminosulfonyl)benzyl]amino}-1,3,4-thiadiazol-2-yl)-3-phenyl-2-propenamide,
  • 32) (E)-N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)-1,3,4-thiadiazol-2-yl]-9-octadecenamide,
  • 33) (E)-N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-9-octadecenamide,
  • 34) (E)-N-[5-(cycloheptylamino)-1,3,4-thiadiazol-2-yl]-9-octadecenamide,
  • 35) (E)-N-{5-[(4-fluorobenzyl)amino]-1,3,4-thiadiazol-2-yl}-9-octadecenamide,
  • 36) 2,6-dichloro-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}benzamide, or
  • 37) N-(5-{[4-(aminosulfonyl)benzyl]amino}-1,3,4-thiadiazol-2-yl)-2-ethoxy-1-naphthamide.
  • 9. A compound of claim 1 which is
  • 1) N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-2-ethoxy-1-naphthamide,
  • 2) N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide,
  • 3) N-{5-[(3,3-diphenylpropyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide,
  • 4) N-{5-[(2,2-diphenylethyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide,
  • 5) 1,3-dioxo-N-[5-(undecylamino)-1,3,4-thiadiazol-2-yl]-1,3-dihydro-2-benzofuran-5-carboxamide,
  • 6) N-[5-({[(2R)-6,6-dimethylbicyclo[3.1.1]hept-2-yl]methyl}amino)-1,3,4-thiadiazol-2-yl]-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide,
  • 7) 1,3-dioxo-N-{5-[(4-phenylbutyl)amino]-1,3,4-thiadiazol-2-yl}-1,3-dihydro-2-benzofuran-5-carboxamide,
  • 8) N-(5-{[2-(1H-indol-3-yl)ethyl]amino}-1,3,4-thiadiazol-2-yl)-1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxamide, or
  • 9) (E)-N-(5-{[3-(cyclohexylamino)propyl]amino}-1,3,4-thiadiazol-2-yl)-9-octadecenamide.
  • 10. A pharmaceutical composition which comprises an effective amount of the compound of claim 1 to treat cytomegalovirus infection and a pharmaceutically acceptable carrier.
  • 11. A method for treating viral infections in a mammal comprising administering to said mammal in need thereof an effective amount of a compound of formula I of claim 1.
  • 12. A method of claim 11 wherein said effective amount of a compound of formula is administered orally, parenterally or topically in a pharmaceutical composition.
  • 13. A method of claim 11 wherein said viral infection is human cytomegalovirus infection.
  • 14. A method of claim 11 wherein said effective amount of a compound of formula is administered in an amount of from about 0.1 to 300 mg/kg of mammal body weight.
CROSS-REFERENCE TO RELATED APPLICATIONS

This application claims the benefit of provisional application U.S. Ser. No. 60/078,528, filed Mar. 19, 1998, under 35 USC 119(e)(i).

Foreign Referenced Citations (1)
Number Date Country
0 061 434A Sep 1982 EPX