IP Library › Granted Patent US 8,802,861

Granted Patent B2

US 8,802,861 · App. 10/585,635 · Granted Aug 12, 2014

Thiazole derivatives and use thereof

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Patent No.: US 8,802,861
App. No.: 10/585,635
Granted: Aug 12, 2014
Kind: B2

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Abstract

The present invention is related to thiazole derivatives of Formula (I) in particular for the treatment and/or prophylaxis of autoimmune disorders and/or inflammatory diseases, cardiovascular diseases, neurodegenerative diseases, bacterial or viral infections, kidney diseases, platelet aggregation, cancer, transplantation, graft rejection or lung injuries.

Claims (277)

1. A thiazole according to Formula (I),

wherein R 1 is a moiety of the formula —NR 5 R 6 ;

R 2 , R 3 and R 5 are selected independently from the group consisting of H, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl and C 2 -C 6 -alkynyl;

R 4 is selected from the group consisting of H, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl and NR 8 R 9 , wherein R 8 and R 9 are independently selected from the group consisting of H, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkyl alkoxy carbonyl and C 1 -C 6 -alkyl acyloxy;

R 6 is an unsubstituted group selected from the group consisting of

C 2 -C 6 -alkenyl,

C 2 -C 6 -alkynyl,

C 1 -C 6 -alkyl alkoxy,

C 1 -C 6 alkyl acyl,

C 1 -C 6 -alkyl carboxy,

C 1 -C 6 alkyl C 3 -C 8 cycloalkyl,

C 1 -C 6 alkyl heterocycloalkyl,

C 1 -C 6 -alkyl acylamino,

C 1 -C 6 -alkyl amino,

C 1 -C 6 -alkyl aminocarbonyl,

C 1 -C 6 -alkyl alkoxycarbonyl,

2-acetylamino-phenyl,

3-nitro phenyl,

2-nitrophenyl,

2-methylphenyl,

2-chlorophenyl,

3-chlorophenyl,

2-hydroxyphenyl,

4-hydroxyphenyl,

cyanophenyl,

3-(1-hydroxyethyl)phenyl,

hydroxamic acid phenyl,

3-(N-hydroxycarbamimidoyl)-phenyl-4-yl,

benzyl piperazine carbonyl phenyl,

phenyl substituted with heteroaryl,

dimethylpyrimidine amino sulfonyl phenyl,

methyl isoxazol amino sulfonyl phenyl,

dimethoxy pyrimidine amino sulfonyl phenyl,

pyridinyl amino sulfonyl phenyl,

3-(aminosulfonyl)phenyl,

4[(methylamino)sulfonyl]phenyl,

4-[(dimethylamino)sulfonyl]phenyl,

3 [(butylamino)sulfonyl]phenyl,

4-(morpholin-4-yl-sulfonyl)phenyl,

aryl sulfonyl,

fused phenyl,

3-pyridine,

4-pyridine,

methoxy pyridine,

chloro pyridine,

fluoro pyridine,

cyano pyridine,

acetamide pyridine,

fused pyridine,

C 3 -C 8 cycloalkyl,

pyridine-3-yl-methyl,

pyridine-4-yl-methyl,

2-(1H-tetrazol-5-yl)ethyl,

2-(2-hydroxy-1,3,4-oxadiazol-5-yl)ethyl,

3-(2-hydroxy-1,3,4-oxadiazol-5-yl)propyl, and

3-(1H-imidazol-1-yl)propyl;

or R 5 and R 6 , together with the carbon atoms they are linked to, form an unsubstituted 5-8-membered saturated ring or aromatic ring containing optionally one or more heteroatoms selected from the group consisting of 0, N and S; and

X is S;

as well as isomers thereof.

2. The thiazole according to claim 1 ; wherein R 2 is H.

3. The thiazole according to claim 1 ; wherein R 3 is methyl.

4. The thiazole according to claim 1 ; wherein R 4 is selected from the group consisting of C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl and C 2 -C 6 -alkynyl.

5. The thiazole according to claim 1 ; wherein R 5 is H and R 6 is unsubstituted and selected from the group consisting of C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, and C 1 -C 6 -alkyl alkoxy.

6. The thiazole according to claim 1 ; wherein R 5 is H.

7. The thiazole according to claim 1 ; wherein R 5 is H and R 6 is unsubstituted and selected from the group consisting of 2-hydroxyphenyl, 4-hydroxyphenyl, 2-acetylamino-phenyl, dimethylpyrimidine amino sulfonyl phenyl, pyridinyl amino sulfonyl phenyl, 3-(aminosulfonyl)phenyl, 4[(methylamino)sulfonyl]phenyl, 4-[(dimethylamino)sulfonyl]phenyl, 3[(butylamino)sulfonyl]phenyl, 4-(morpholin-4-yl-sulfonyl)phenyl, 2-chlorophenyl, 3-chlorophenyl, 2-methylphenyl, 3-nitro phenyl, 2-nitrophenyl, cyanophenyl, 3-(1-hydroxyethyl)phenyl, hydroxamic acid phenyl, 3-(N-hydroxycarbamimidoyl)-phenyl-4-yl, benzyl piperazine carbonyl phenyl, and phenyl substituted with heteroaryl.

8. The thiazole according to claim 1 ; wherein R 5 and R 6 , together with the carbon atoms they are linked to, form a 5-8-membered saturated or aromatic ring containing optionally one or more heteroatoms selected from the group consisting of O, N and S.

9. The thiazole according to claim 1 ; wherein R 1 is —NR 5 R 6 ; R 2 is H; R 3 is methyl; R 4 is selected from the group consisting of C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl and —NR 8 R 9 ; wherein R 8 and R 9 are independently selected from the group consisting of H, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl and C 1 -C 6 -alkyl alkoxycarbonyl; R 5 is H and R 6 is unsubstituted and selected from the group consisting of C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkyl alkoxy, C 1 -C 6 -alkyl carboxy, C 1 -C 6 -alkyl acylamino, C 1 -C 6 -alkyl amino, C 1 -C 6 -alkyl aminocarbonyl, C 1 -C 6 -alkyl alkoxycarbonyl, C 1 -C 6 -alkyl C 3 -C 8 -cycloalkyl and C 1 -C 6 -alkyl heterocycloalkyl; and X is S.

10. The thiazole according to claim 1 ; wherein R 1 is —NR 5 R 6 ; R 2 is H; R 3 is methyl; R 4 is selected from the group consisting of C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, an C 2 -C 6 -alkynyl and —NR 8 R 9 wherein R 8 and R 9 are independently selected from the group consisting of H, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl and C 1 -C 6 -alkyl alkoxycarbonyl; R 5 is H; and X is S.

11. The thiazole according to claim 1 ; wherein R 1 is —NR 5 R 6 ; R 2 is H; R 3 is methyl; R 4 is an unsubstituted C 1 -C 6 -alkyl, and —NR 8 R 9 ; wherein R 8 and R 9 are independently selected from the group consisting of H, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl and C 1 -C 6 -alkyl alkoxycarbonyl; R 5 is H; and X is S.

12. The thiazole according to claim 1 ; wherein R 1 is —NR 5 R 6 ; R 2 is H; R 3 is methyl; R 4 is an unsubstituted C 1 -C 6 -alkyl, and —NR 8 R 9 wherein R 8 and R 9 are independently selected from the group consisting of H, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl and C 1 -C 6 -alkyl alkoxycarbonyl; R 5 and R 6 , together with the carbon atoms they are linked to, form an optionally substituted 5-8-membered saturated or aromatic ring containing optionally one or more heteroatoms selected from the group consisting of O, N and S; and X is S.

13. A thiazole selected from the group consisting of:

N-(4′-methyl-2-piperidin-1-yl-4,5′-bi-1,3-thiazol-2′-yl)acetamide;

N-[4′-methyl-2-(pyridin-3-ylamino)-4,5′-bi-1,3-thiazol-2′-yl]acetamide;

N-(4′-methyl-2-morpholin-4-yl-4,5′-bi-1,3-thiazol-2′-yl)acetamide;

N-[4′-methyl-2-(4-methylpiperazin-1-yl)-4,5′-bi-1,3-thiazol-2′-yl]acetamide;

methyl 1-[2-(acetylamino)-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl]piperidine-3 carboxylate;

N-{2-[4-(2-hydroxyethyl)piperidin-1-yl]-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl}acetamide;

N-(4′-methyl-2-pyrrolidin-1-yl-4,5′-bi-1,3-thiazol-2′-yl)acetamide;

N-[2-(3-hydroxypyrrolidin-1-yl)-4′methyl-4,5′-bi-1,3-thiazol-2′-yl]acetamide;

N-[2-(tert-butylamino)-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl]acetamide;

N-{2-[(6-methoxypyridin-3-yl)amino]-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl}acetamide;

N-{2-[(6-chloropyridin-3-yl)amino]-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl}acetamide;

N-{4′-methyl-2-[(2-morpholin-4-ylethyl)amino]-4,5′-bi-1,3-thiazol-2′-yl}acetamide;

N-{4′-methyl-2-[(2-piperidin-1-ylethyl)amino]-4,5′-bi-1,3-thiazol-2′-yl}acetamide;

N-{2-[(2-methoxyethyl)amino]-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl}acetamide;

N-[2-(cyclohexylamino)-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl]acetamide;

N-{4′-methyl-2-[(3-morpholin-4-ylpropyl)amino]-4,5′-bi-1,3-thiazol-2′-yl}acetamide;

N-{4′-methyl-2-[(tetrahydrofuran-2-ylmethyl)amino]-4,5′-bi-1,3-thiazol-2′-yl}acetamide;

N-[2-(1-benzofuran-5-ylamino)-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl]acetamide;

[4′-methyl-2-(pyridin-3-ylamino)-4,5′-bi-1,3-thiazol-2′-yl]formamide;

N-{2-[(2-fluoropyridin-3-yl)amino]-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl}acetamide;

N-{2-[(2-cyanoethyl)amino]-4′-methyl-4, 5 ‘-bi-1,3-thiazol-2’-yl}acetamide;

N-{2-[(3,3-diethoxypropyl)amino]-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl}acetamide;

N-{2-[(2,2-diethoxyethyl)amino]-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl}acetamide;

N-{4′-methyl-2-[(2-oxo-2-phenylethyl)amino]-4,5′-bi-1,3-thiazol-2′-yl}acetamide;

N-{2-[(2-chloropyridin-3-yDamino]-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl}acetamide;

N-[2′-(acetylamino)-4′-methyl-4,5′-bi-1,3-thiazol-2-yl]-beta-alanine;

4-{[2′-(acetylamino)-4′-methyl-4,5′-bi-1,3-thiazol-2-yl]amino}butanoic acid;

N-{2-[(2-chloropyridin-4-yDamino]-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl}acetamide;

N-(5-{[2′-(acetylamino)-4′-methyl-4,5′-bi-1,3-thiazol-2-yl]amino}pyridin-2-yl) acetamide;

N-[2-(2,3-dihydro-1-benzofuran-5-ylamino)-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl]acetamide;

N-(4′-methyl-2-{[2-(1-methylpyrrolidin-2-yl)ethyl]amino}-4,5′-bi-1,3-thiazol-2′-yl) acetamide;

N-{4′-methyl-2-[(2-pyrrolidin-1-ylethyl)amino]-4,5′-bi-1,3-thiazol-2′-yl}acetamide;

N-(4′-methyl-2-{[3-(2-oxopyrrolidin-1-yl)propyl]amino}-4,5′-bi-1,3-thiazol-2′-yl) acetamide;

N-(2-{[2-(acetylamino)ethyl]amino}-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl) acetamide;

N-(2-{[2-(dimethylamino)ethyl]amino}-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl) acetamide;

N-{2-[(2-hydroxyethyl)amino]-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl}acetamide;

N-(2-{[3-(dimethylamino)propyl]amino}-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl) acetamide;

N-{2-[(3-hydroxypropyl)amino]-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl}acetamide;

N˜3˜-[2′-(acetylamino)-4′-methyl-4,5′-bi-1,3-thiazol-2-yl]-beta-alaninamide;

N-{2-[(6-cyanopyridin-3-yDamino]-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl}acetamide;

N-[4′-methyl-2-(quinolin-3-ylamino)-4,5′-bi-1,3-thiazol-2′-yl]acetamide;

N-[4′-methyl-2-(quinolin-5-ylamino)-4,5′-bi-1,3-thiazol-2′-yl]acetamide;

N-[4′-methyl-2-(quinolin-6-ylamino)-4,5′-bi-1,3-thiazol-2′-yl]acetamide;

N-[2-(cyclopentylamino)-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl]acetamide;

N-[2-(cyclopropylamino)-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl]acetamide;

N-{2-[(4-hydroxybutyl)amino]-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl}acetamide;

N-{4′-methyl-2-[(3-pyrrolidin-1-ylpropyl)amino]-4,5′-bi-1,3-thiazol-2′-yl}acetamide;

N-{2-[(1,1-dioxido-1-benzothien-6-yl)amino]-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl}acetamide;

N-(2-{[(1-ethylpyrrolidin-2-yl)methyl]amino}-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl) acetamide;

N-{2-[(cyanomethyl)amino]-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl}acetamide;

N-[2-(isobutylamino)-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl]acetamide;

N-{2-[(2,2-dimethylpropyl)amino]-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl}acetamide;

N-(2-{[(cis)-2-(hydroxymethyl)cyclohexyl]amino}-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl)acetamide;

N-(2-{[(trans)-2-(hydroxymethyl)cyclohexyl]amino}-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl)acetamide;

N-[2-(sec-butylamino)-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl]acetamide;

N-{2-[(cyclopropylmethyl)amino]-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl}acetamide;

N-{2-(cyclobutylamino)-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl}acetamide;

N-[2-(2,3-dihydro-1H-inden-2-ylamino)-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl]acetamide;

methyl 4-{[2′-(acetylamino)-4′-methyl-4,5′-bi-1,3-thiazol-2-yl]amino}butanoate;

N-[4′-methyl-2-(pyridin-3-ylamino)-4,5′-bi-1,3-thiazol-2′-yl]urea; and

N-(4′-methyl-2-piperidin-1-yl-4,5′-bi-1,3-thiazol-2′-yl)urea.

14. A pharmaceutical composition, comprising:

at least one thiazole derivative according to claim 1 ; and

a pharmaceutically acceptable carrier, diluent or excipient thereof.

15. A thiazole compound selected from the group consisting of:

3-{[2′-(acetylamino)-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl]amino}benzoic acid;

4-{[2′-(acetylamino)-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl]amino}benzoic acid;

N-[2-(benzylamino)-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl]acetamide;

N-{4′-methyl-2-[(2-phenylethyl)amino]-4,5′-bi-1,3-thiazol-2′-yl}acetamide;

N-(4′-methyl-2-piperidin-1-yl-4,5′-bi-1,3-thiazol-2′-yl)acetamide;

N-[2-(allylamino)-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl]acetamide;

N-[4′-methyl-2-(pyridin-3-ylamino)-4,5′-bi-1,3-thiazol-2′-yl]acetamide;

N-[4′-methyl-2-(pyridin-2-ylamino)-4,5′-bi-1,3-thiazol-2′-yl]acetamide;

N-{2-[(4-hydroxyphenyl)amino]-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl}acetamide;

N-{4′-methyl-2-[(4-nitrophenyl)amino]-4,5′-bi-1,3-thiazol-2′-yl}acetamide;

4-{[2′-(acetylamino)-4-methyl-4,5′-bi-1,3-thiazol-2′-yl]amino}benzamide;

N-[2-({4-[(4-benzylpiperazin-1-yl)carbonyl]phenyl}amino)-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl]acetamide;

N-(4′-methyl-2-morpholin-4-yl-4,5′-bi-1,3-thiazol-2′-yl)acetamide;

N-[4′-methyl-2-(4-methylpiperazin-1-yl)-4,5′-bi-1,3-thiazol-2′-yl]acetamide;

methyl 1-[2′-(acetylamino)-4′-methyl-4,5′-bi-1,3-thiazol-2-yl]piperidine-3-carboxylate;

N-{2-[4-(2-hydroxyethyl)piperidin-1-yl]-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl}acetamide;

N-(4′-methyl-2-pyrrolidin-1-yl-4,5′-bi-1,3-thiazol-2′-yl)acetamide;

N-[2-(3-hydroxypyrrolidin-1-yl)-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl]acetamide;

N-[2-(tert-butylamino)-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl]acetamide;

N-{2-[(6-methoxypyridin-3-yl)amino]-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl}acetamide;

N-{2-[(6-chloropyridin-3-yDamino]-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl}acetamide;

N-{2-[(4-cyanophenyl)amino]-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl}acetamide;

N-{2-[(2-chlorophenyl)amino]-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl}acetamide;

N-{2-[(3-chlorophenyl)amino]-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl}acetamide;

N-{2-[(3-hydroxyphenyl)amino]-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl}acetamide;

N-{4′-methyl-2-[(2-morpholin-4-ylethyl)amino]-4,5′-bi-1,3-thiazol-2′-yl}acetamide;

N-{4′-methyl-2-[(2-piperidin-1-ylethyl)amino]-4,5′-bi-1,3-thiazol-2′-yl}acetamide;

N-{2-[(2-methoxyethyl)amino]-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl}acetamide;

N-[2-(cyclohexylamino)-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl]acetamide;

N-{4′-methyl-2-[(3-morpholin-4-ylpropyl)amino]-4,5′-bi-1,3-thiazol-2′-yl}acetamide;

N-{4′-methyl-2-[(tetrahydrofuran-2-ylmethyl)amino]-4,5′-bi-1,3-thiazol-2′-yl}acetamide;

N-{2-[(2-hydroxy-2-phenylethyl)amino]-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl}acetamide;

N-[2-(1-benzofuran-5-ylamino)-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl]acetamide;

N-{2-[(3-cyanophenyl)amino]-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl}acetamide;

[4′-methyl-2-(pyridin-3-ylamino)-4,5′-bi-1,3-thiazol-2′-yl]formamide;

ethyl N-({[2-(allylamino)-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl]amino}carbonyl)-beta-alaninate;

N-{2-[(2-fluoropyridin-3-yl)amino]-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl}acetamide;

N-{2-[(2-cyanoethyl)amino]-4′-methyl-4, 5 ‘-bi-1,3-thiazol-2’-yl}acetamide;

N-{2-[(3,3-diethoxypropyl)amino]-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl}acetamide;

N-{2-[(2,2-diethoxyethyl)amino]-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl}acetamide;

N-{4′-methyl-2-[(2-oxo-2-phenylethyl)amino]-4,5′-bi-1,3-thiazol-2′-yl}acetamide;

N-{2-[(2-chloropyridin-3-yl)amino]-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl}acetamide;

N-(4′-methyl-2-{[3-(1,3-oxazol-5-yl)phenyl]amino}-4,5′-bi-1,3-thiazol-2′-yl) acetamide;

N-(4′-methyl-2-{[3-(1H-tetrazol-5-yl)phenyl]amino}-4,5′-bi-1,3-thiazol-2′-yl) acetamide;

N-(4′-methyl-2-[4-(1H-tetrazol-5-yl)phenyl]amino}-4,5′-bi-1,3-thiazol-2′-yl) acetamide;

N-{4′-Methyl-2-[2-(1H-tetrazol-5-yl)-ethylamino]-[4,5]bithiazolyl-2′-yl}-acetamide;

N-(2-{[3-(5-hydroxy-1,3,4-oxadiazol-2-yl)phenyl]amino}-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl)acetamide;

N-(2-{[3-(5-amino-1,3,4-thiadiazol-2-yl)phenyl]amino}-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl)acetamide;

N-[2′-(acetylamino)-4′-methyl-4,5′-bi-1,3-thiazol-2-yl]-beta-alanine;

5-(2-{[2′-(acetylamino)-4′-methyl-4,5′-bi-1,3-thiazol-2-yl]amino}ethyl)-1,3,4-oxadiazol-2-olate;

4-{[2′-(acetylamino)-4′-methyl-4,5′-bi-1,3-thiazol-2-yl]amino}butanoic acid;

N-(2-{[3-(5-hydroxy-1,3,4-oxadiazol-2-yl)propyl]amino}-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl)acetamide;

3-{[2′-(acetylamino)-4′-methyl-4,5′-bi-1,3-thiazol-2-yl]amino}-N-hydroxy benzamide;

3-{[2′-(acetylamino)-4′-methyl-4,5′-bi-1,3-thiazol-2-yl]amino}-N-hydroxy benzene carboximidic acid;

N-(2-{[3-(5-hydroxy-1,2,4-oxadiazol-3-yl)phenyl]amino}-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl)acetamide;

N-[2-({3-[(Z)-(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenyl}amino)-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl]acetamide;

N-[4′-methyl-2-({4-[(pyridin-2-ylamino)sulfonyl]phenyl}amino)-4,5′-bi-1,3-thiazol-2′-yl]acetamide;

N-(2-{[2-(2-hydroxyethyl)phenyl]amino}-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl) acetamide;

N-(2-{[3-(hydroxymethyl)phenyl]amino}-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl) acetamide;

N-(2-{[4-(2-hydroxyethyl)phenyl]amino}-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl) acetamide;

N-[2-({3-[(2-hydroxyethyl)sulfonyl]phenyl}amino)-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl]acetamide;

N-[2-({4-[(dimethylamino)sulfonyl]phenyl}amino)-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl]acetamide;

N-(2-{[3-(aminosulfonyl)phenyl]amino}-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl) acetamide;

N-{2-[(2-chloropyridin-4-yl)amino]-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl}acetamide;

N-[4′-methyl-2-({4-[(methylamino)sulfonyl]phenyl}amino)-4,5′-bi-1,3-thiazol-2′-yl]acetamide;