US 8,802,861 B2Granted

Thiazole derivatives and use thereof

AssigneeMerck Serono SA

InventorsAnna Quattropani, Thomas Rueckle, Matthias Schwarz, Jerome Dorbais, Wolfgang Sauer, Christophe Cleva, Gwenaelle Desforges

Life of this patent

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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.

Claims15

Dependent claims

A thiazole according to Formula (I),

wherein R1 is a moiety of the formula —NR5R6;
R2, R3 and R5 are selected independently from the group consisting of H, C1-C6-alkyl, C2-C6-alkenyl and C2-C6-alkynyl;
R4 is selected from the group consisting of H, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl and NR8R9, wherein R8 and R9 are independently selected from the group consisting of H, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkyl alkoxy carbonyl and C1-C6-alkyl acyloxy;
R6 is an unsubstituted group selected from the group consisting of
C2-C6-alkenyl,
C2-C6-alkynyl,
C1-C6-alkyl alkoxy,
C1-C6 alkyl acyl,
C1-C6-alkyl carboxy,
C1-C6 alkyl C3-C8 cycloalkyl,
C1-C6 alkyl heterocycloalkyl,
C1-C6-alkyl acylamino,
C1-C6-alkyl amino,
C1-C6-alkyl aminocarbonyl,
C1-C6-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,
C3-C8 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 R5 and R6, 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.

56 more elements

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.

59 more elements

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;
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-{[2-(4-hydroxyphenyl)ethyl]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-(2-{[3-(1H-imidazol-1-yl)propyl]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-{4′-methyl-2-[(2-methylprop-2-en-1-yl)amino]-4,5′-bi-1,3-thiazol-2′-yl}acetamide;
N-{2-[(2-hydroxyphenyl)amino]-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl}acetamide;
N-{2-[(6-fluoropyridin-3-yl)amino]-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-[(6-cyanopyridin-3-yl)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}benzamide;
N-{4′-methyl-2-[(2-nitrophenyl)amino]-4,5′-bi-1,3-thiazol-2′-yl}acetamide;
N-{4′-methyl-2-[(3-nitrophenyl)amino]-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-{4′-methyl-2-[(pyridin-3-ylmethyl)amino]-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-(methylsulfonyl)phenyl]amino}-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-{4′-methyl-2-[(pyridin-4-ylmethyl)amino]-4,5′-bi-1,3-thiazol-2′-yl}acetamide;
N-(4′-methyl-2-{[4-(morpholin-4-ylsulfonyl)phenyl]amino}-4,5′-bi-1,3-thiazol-2′-yl) acetamide;
N-[2-({3-[(butylamino)sulfonyl]phenyl}amino)-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;
N-(4′-methyl-2-{[2-(methylsulfonyl)phenyl]amino}-4,5′-bi-1,3-thiazol-2′-yl) acetamide;
N-(4′-methyl-2-{[2-(1H-1,2,4-triazol-1-yl)ethyl]amino}-4,5′-bi-1,3-thiazol-2′-yl) acetamide;
N-(2-{[3-(1-hydroxyethyl)phenyl]amino}-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}phenyl)acetate;
methyl N-(4-{[2′-(acetylamino)-4′-methyl-4,5′-bi-1,3-thiazol-2-yl]amino}benzoyl)-beta-alaninate;
methyl N-(4-{[2′-(acetylamino)-4′-methyl-4,5′-bi-1,3-thiazol-2-yl]amino}benzoyl)glycinate;
methyl 3-(3-{[2′-(acetylamino)-4′-methyl-4,5′-bi-1,3-thiazol-2-yl]amino}phenyl) propanoate;
3-(4-{[2′-(acetylamino)-4′-methyl-4,5′-bi-1,3-thiazol-2-yl]amino}phenyl) propanoic acid;
methyl 4-{[2′-(acetylamino)-4′-methyl-4,5′-bi-1,3-thiazol-2-yl]amino}butanoate;
methyl (3-{[2′-(acetylamino)-4′-methyl-4,5′-bi-1,3-thiazol-2-yl]amino}phenyl)acetate;
N-[2-(allylamino)-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl]urea;
N-[4′-methyl-2-(pyridin-3-ylamino)-4,5′-bi-1,3-thiazol-2′-yl]urea;
N-(4′-methyl-2-piperidin-1-yl-4,5′-bi-1,3-thiazol-2′-yl)urea;
N-(2-anilino-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl)urea;
N-{2-[(4-hydroxyphenyl)amino]-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl}urea;
N-[2-(pyridin-3-ylamino)-4,5′-bi-1,3-thiazol-2′-yl]acetamide;
(4-{[2′-(acetylamino)-4′-methyl-4,5′-bi-1,3-thiazol-2-yl]amino}phenyl)acetic acid;
N-(4-{[2′-(acetylamino)-4′-methyl-4,5′-bi-1,3-thiazol-2-yl]amino}benzoyl)-beta-alanine;
N-(4-{[2′-(acetylamino)-4′-methyl-4,5′-bi-1,3-thiazol-2-yl]amino}benzoyl)glycine;
3-(3-{[2′-(acetylamino)-4′-methyl-4,5′-bi-1,3-thiazol-2-yl]amino}phenyl) propanoic acid;
N-{2-[(4-ethoxyphenyl)amino]-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl}acetamide;
N-{4′-methyl-2-[(4-methylphenyl)amino]-4,5′-bi-1,3-thiazol-2′-yl}acetamide;
N-{2-[(4-{[(4,6-dimethylpyrimidin-2-yl)amino]sulfonyl}phenyl)amino]-4,5′-bi-1,3-thiazol-2′-yl}acetamide;
N-{4′-methyl-2-[(4-{[(5-methylisoxazol-3-yl)amino]sulfonyl}phenyl)amino]-4,5′-bi-1,3-thiazol-2′-yl}acetamide;
N-[2-(allylamino)-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl]propanamide;
N-{2-[(4-{[(2,6-dimethoxypyrimidin-4-yl)amino]sulfonyl}phenyl)amino]-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl}acetamide;
N-{4′-methyl-2-[(4-{[(5-methylisoxazol-3-yl)amino]sulfonyl}phenyl)amino]-4,5′-bi-1,3-thiazol-2′-yl}propanamide;
N-{2-[(4-{[(4,6-dimethylpyrimidin-2-yl)amino]sulfonyl}phenyl)amino]-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl}propanamide;
N-{2[(2-ethylphenyl)amino]-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl}acetamide;
N-{4′-methyl-2[(2-methylphenyl)amino]-4,5′-bi-1,3-thiazol-2′-yl}acetamide;
N-{2-[(2,5-dimethoxyphenyl)amino]-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl}acetamide;
and
N-{2-[(3-acetylphenyl)amino]-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl}acetamide.

139 more elements

Dependencies are inferred from the claim text.

Facts

Application: 10/585,635Filed 11 Jan 2005
Priority: EP 0410008312 Jan 2004
Published: US 2009/0029998 A129 Jan 2009
Granted: 12 Aug 2014
Term ends: Not estimatedThe source records don’t support an estimate.

Classification31 codes

C07D 417/04
Containing two hetero rings: directly linked by a ring-member-to-ring-member bond
A61P 1/04
Drugs for disorders of the alimentary tract or the digestive system: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of…
A61P 7/02
Drugs for disorders of the blood or the extracellular fluid: antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
A61P 9/00
Drugs for disorders of the cardiovascular system

Family

US 2009/0029998 A1Pre-grant publication · published 29 Jan 2009
US 8,802,861 B2This patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

A thiazole according to Formula (I),

wherein R1 is a moiety of the formula —NR5R6;
R2, R3 and R5 are selected independently from the group consisting of H, C1-C6-alkyl, C2-C6-alkenyl and C2-C6-alkynyl;
R4 is selected from the group consisting of H, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl and NR8R9, wherein R8 and R9 are independently selected from the group consisting of H, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkyl alkoxy carbonyl and C1-C6-alkyl acyloxy;
R6 is an unsubstituted group selected from the group consisting of
C2-C6-alkenyl,
C2-C6-alkynyl,
C1-C6-alkyl alkoxy,
C1-C6 alkyl acyl,
C1-C6-alkyl carboxy,
C1-C6 alkyl C3-C8 cycloalkyl,
C1-C6 alkyl heterocycloalkyl,
C1-C6-alkyl acylamino,
C1-C6-alkyl amino,
C1-C6-alkyl aminocarbonyl,
C1-C6-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,
C3-C8 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 R5 and R6, 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.

56 more elements

Facts

Application

10/585,635Filed 11 Jan 2005

Priority

EP 0410008312 Jan 2004

Published

US 2009/0029998 A129 Jan 2009

Granted

12 Aug 2014

Term ends

Not estimatedThe source records don’t support an estimate.

Classification31 codes

C07D 417/04
Containing two hetero rings: directly linked by a ring-member-to-ring-member bond
A61P 1/04
Drugs for disorders of the alimentary tract or the digestive system: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of…
A61P 7/02
Drugs for disorders of the blood or the extracellular fluid: antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
A61P 9/00
Drugs for disorders of the cardiovascular system