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US 7,678,815 B2Granted

Thiazole-4-carboxyamide derivatives

AssigneeHoffmann-La Roche Inc.

InventorsBernd Buettelmann, Simona Maria Ceccarelli, Georg Jaeschke, Sabine Kolczewski, Richard Hugh Philip Porter, Eric Vieira

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Abstract

The present invention is concerned with novel thiazole 4-carboxyamide derivatives of the general formula (I) and with methods for the preparation thereof, which compounds are useful as metabotropic glutamate receptor antagonists: wherein R1 to R4 are as defined in the specification.

Claims25

Dependent claims

A compound of formula (I):

wherein
R1 is aryl or heteroaryl, each of which is optionally substituted by one or more substituents selected from the group consisting of —OH, chloro, fluoro, bromo, cyano, C1-C7-alkyl, C1-C7-alkoxy, —O—(CO)—C1-C7-alkyl, C3-C6-cycloalkyl, and —(CH2)m—Ra,
wherein Ra is —OH, —CH2F, —CHF2, —CF3, C1-C7-alkoxy, C3-C6-cycloalkyl, —NH(CO)—C1-C7-alkyl, or —O—(CO)—C1-C7-alkyl;
R2 is H, C1-C7-alkyl, —(CH2)m—O—C1-C7-alkyl or C3-C6-cycloalkyl;
R3 is C1-C7-alkyl;
—(CH2)m—Rb,
wherein Rb is —O—C1-C7-alkyl, C3-C6-cycloalkyl, 5 or 6 membered heterocycloalkyl, aryl optionally substituted by fluoro, or heteroaryl optionally substituted by C1-C7-alkyl;
—(CO)—Rc,
wherein Rc is —O—(CH2)m—C3-C6-cycloalkyl, or aryl;
C3-C6-cycloalkyl;
5 or 6 membered heterocycloalkyl;
aryl or heteroaryl, each of which is optionally substituted by
cyano,
chloro,
fluoro,
bromo,
CF3,
CHF2,
C3-C6-cycloalkyl, or
—O—C1-C7-alkyl;
—(CO)—Rd,
wherein Rd is C1-C7-alkyl, NH2, or —O—C1-C7-alkyl;
—(CH2)m—Re,
wherein Re is OH, C1-C7-alkoxy, CHF2, CF3, NH2, —NH—(CO)—C1-C7-alkyl, or —NH—(CO)—O—C1-C7-alkyl;
—NH—(CO)—C1-C7-alkyl;
—O—CH2F;
—O—CHF2;
—O—CF3;
—S(O)2—Rf,
wherein Rf is C1-C7-alkyl, —NH2, —NH—C1-C7-alkyl or —N-di(C1-C7-alkyl);
or heteroaryl optionally substituted by C1-C7-alkyl;
R4 is H, C1-C7-alkyl or C1-C7-alkyl-C3-C6-cycloalkyl;
m is 1 to 4;
or a pharmaceutically acceptable salt thereof.

31 more elements

A compound of 4, selected from the group consisting of:

5-(Pyridin-3-ylamino)-thiazole-4-carboxylic acid (6-methyl-pyridin-2-yl)-amide;
5-(Pyridin-3-ylamino)-thiazole-4-carboxylic acid (3-chloro-phenyl)-amide;
5-(Pyridin-3-ylamino)-thiazole-4-carboxylic acid (6-chloro-pyridin-2-yl)-amide;
5-(Pyridin-3-ylamino)-thiazole-4-carboxylic acid (6-bromo-pyridin-2-yl)-amide;
5-(Pyridin-3-ylamino)-thiazole-4-carboxylic acid (4-methyl-thiazol-2-yl)-amide;
5-(Pyridin-3-ylamino)-thiazole-4-carboxylic acid (2-methyl-thiazol-4-yl)-amide;
5-(Pyridin-3-ylamino)-thiazole-4-carboxylic acid m-tolylamide;
5-(Pyridin-3-ylamino)-thiazole-4-carboxylic acid (6-ethyl-pyridin-2-yl)-amide;
5-(Pyridin-3-ylamino)-thiazole-4-carboxylic acid (6-trifluoromethyl-pyridin-2-yl)-amide;
5-(3,5-Dimethyl-isoxazol-4-ylamino)-thiazole-4-carboxylic acid (3-chloro-phenyl)-amide;
5-(3,5-Dimethyl-isoxazol-4-ylamino)-thiazole-4-carboxylic acid m-tolylamide;
5-(3,5-Dimethyl-isoxazol-4-ylamino)-thiazole-4-carboxylic acid (6-methyl-pyridin-2-yl)-amide;
5-(3,5-Dimethyl-isoxazol-4-ylamino)-thiazole-4-carboxylic acid (6-bromo-pyridin-2-yl)-amide;
5-(3,5-Dimethyl-isoxazol-4-ylamino)-thiazole-4-carboxylic acid (4-methyl-thiazol-2-yl)-amide;
5-(2-Methoxy-pyridin-3-ylamino)-thiazole-4-carboxylic acid (6-methyl-pyridin-2-yl)-amide;
2-Methyl-5-(pyridin-3-ylamino)-thiazole-4-carboxylic acid (3-chloro-phenyl)-amide;
2-Methyl-5-(pyridin-3-ylamino)-thiazole-4-carboxylic acid (6-methyl-pyridin-2-yl)-amide;
2-Methyl-5-(pyridin-3-ylamino)-thiazole-4-carboxylic acid (2-methyl-thiazol-4-yl)-amide;
2-Methyl-5-(pyridin-3-ylamino)-thiazole-4-carboxylic acid (6-chloro-pyridin-2-yl)-amide;
2-Methyl-5-(pyridin-3-ylamino)-thiazole-4-carboxylic acid (6-bromo-pyridin-2-yl)-amide;
2-Methyl-5-(pyridin-3-ylamino)-thiazole-4-carboxylic acid (3-cyano-phenyl)-amide;
2-Methyl-5-(pyridin-3-ylamino)-thiazole-4-carboxylic acid (2-fluoro-5-methyl-phenyl)-amide;
2-Methyl-5-(pyridin-3-ylamino)-thiazole-4-carboxylic acid (5-chloro-2-fluoro-phenyl)-amide;
2-Methyl-5-(pyridin-3-ylamino)-thiazole-4-carboxylic acid (3-chloro-2-fluoro-phenyl)-amide;
2-Methyl-5-(pyridin-3-ylamino)-thiazole-4-carboxylic acid m-tolylamide;
2-Methyl-5-(pyridin-3-ylamino)-thiazole-4-carboxylic acid (6-fluoromethyl-pyridin-2-yl)-amide;
2-Methyl-5-(pyridin-3-ylamino)-thiazole-4-carboxylic acid (2-chloro-pyridin-4-yl)-amide;
2-Methyl-5-(pyridin-3-ylamino)-thiazole-4-carboxylic acid (2-methyl-pyridin-4-yl)-amide;
2-Methyl-5-(pyridin-3-ylamino)-thiazole-4-carboxylic acid (5-fluoro-pyridin-2-yl)-amide;
2-Methyl-5-(pyridin-3-ylamino)-thiazole-4-carboxylic acid (2-methyl-pyrimidin-4-yl)-amide;
2-Methyl-5-(pyrimidin-5-ylamino)-thiazole-4-carboxylic acid (6-chloro-pyridin-2-yl)-amide;
2-Methyl-5-(pyridin-4-ylamino)-thiazole-4-carboxylic acid (4-methyl-thiazol-2-yl)-amide;
5-(3,5-Difluoromethyl-pyridin-3-ylamino)-2-methyl-thiazole-4-carboxylic acid (4-methyl-thiazol-2-yl)-amide.

30 more elements

A compound of 4, selected from the group consisting of:

2-Methyl-5-(pyrimidin-5-ylamino)-thiazole-4-carboxylic acid (6-methyl-pyridin-2-yl)-amide;
2-Methyl-5-(pyrimidin-5-ylamino)-thiazole-4-carboxylic acid (2-methyl-thiazol-4-yl)-amide;
2-Methyl-5-(pyrimidin-5-ylamino)-thiazole-4-carboxylic acid (2-methyl-pyridin-4-yl)-amide;
2-Methyl-5-(pyrimidin-5-ylamino)-thiazole-4-carboxylic acid (5-fluoro-pyridin-2-yl)-amide;
2-Methyl-5-(pyrimidin-5-ylamino)-thiazole-4-carboxylic acid (3-chloro-phenyl)-amide;
2-Methyl-5-(4-methyl-pyridin-3-ylamino)-thiazole-4-carboxylic acid (3-chloro-phenyl)-amide;
2-Methyl-5-(4-methyl-pyridin-3-ylamino)-thiazole-4-carboxylic acid (6-methyl-pyridin-2-yl)-amide;
2-Methyl-5-(4-methyl-pyridin-3-ylamino)-thiazole-4-carboxylic acid (2-methyl-pyridin-4-yl)-amide;
5-(5-Cyano-pyridin-3-ylamino)-2-methyl-thiazole-4-carboxylic acid (3-chloro-phenyl)-amide;
5-(5-Cyano-pyridin-3-ylamino)-2-methyl-thiazole-4-carboxylic acid (6-methyl-pyridin-2-yl)-amide;
5-Amino-2-methyl-thiazole-4-carboxylic acid (3-chloro-phenyl)-amide;
2-Methyl-5-(pyridin-4-ylamino)-thiazole-4-carboxylic acid (3-chloro-phenyl)-amide;
2-Methyl-5-(2-methyl-pyridin-3-ylamino)-thiazole-4-carboxylic acid (6-methyl-pyridin-2-yl)-amide;
2-Methyl-5-(pyrazin-2-ylamino)-thiazole-4-carboxylic acid (6-methyl-pyridin-2-yl)-amide;
2-Methyl-5-(pyrimidin-2-ylamino)-thiazole-4-carboxylic acid (6-methyl-pyridin-2-yl)-amide;
2-Methyl-5-(pyridin-2-ylamino)-thiazole-4-carboxylic acid (6-methyl-pyridin-2-yl)-amide;
2-Methyl-5-(pyridazin-3-ylamino)-thiazole-4-carboxylic acid (6-methyl-pyridin-2-yl)-amide;
Acetic acid 6-{[2-methyl-5-(pyridin-3-ylamino)-thiazole-4-carbonyl]-amino}-pyridin-2-ylmethyl ester;
2-Methyl-5-(pyridin-3-ylamino)-thiazole-4-carboxylic acid (6-hydroxymethyl-pyridin-2-yl)-amide;
2-Methyl-5-(pyrimidin-5-ylamino)-thiazole-4-carboxylic acid (6-hydroxymethyl-pyridin-2-yl)-amide;
Acetic acid 2-methyl-6-{[2-methyl-5-(pyridin-3-ylamino)-thiazole-4-carbonyl]-amino}-pyridin-3-yl ester;
2-Methyl-5-(pyridin-3-ylamino)-thiazole-4-carboxylic acid (5-hydroxy-6-methyl-pyridin-2-yl)-amide;
2-Methyl-5-(pyrimidin-5-ylamino)-thiazole-4-carboxylic acid (5-hydroxy-6-methyl-pyridin-2-yl)-amide;
2-(2-Methoxy-ethyl)-5-(pyridin-3-ylamino)-thiazole-4-carboxylic acid (6-methyl-pyridin-2-yl)-amide;
2-Methoxymethyl-5-(pyridin-3-ylamino)-thiazole-4-carboxylic acid (6-methyl-pyridin-2-yl)-amide;
2-Cyclopropyl-5-(pyridin-3-ylamino)-thiazole-4-carboxylic acid (6-methyl-pyridin-2-yl)-amide;
2-Cyclobutyl-5-(pyridin-3-ylamino)-thiazole-4-carboxylic acid (6-methyl-pyridin-2-yl)-amide;
2-Ethyl-5-(pyridin-3-ylamino)-thiazole-4-carboxylic acid (6-methyl-pyridin-2-yl)-amide;
2-Propyl-5-(pyridin-3-ylamino)-thiazole-4-carboxylic acid (6-methyl-pyridin-2-yl)-amide;
2-Isopropyl-5-(pyridin-3-ylamino)-thiazole-4-carboxylic acid (6-methyl-pyridin-2-yl)-amide;
2-Methyl-5-(2-methyl-pyridin-3-ylamino)-thiazole-4-carboxylic acid (5-fluoro-pyridin-2-yl)-amide;
2-Methyl-5-(pyrimidin-2-ylamino)-thiazole-4-carboxylic acid (4-methyl-thiazol-2-yl)-amide;
and
2-Methyl-5-[(pyridin-3-ylmethyl)-amino]-thiazole-4-carboxylic acid (4-methyl-thiazol-2-yl)-amide.

31 more elements

A compound of 4, selected from the group consisting of:

2-Methyl-5-((6-trifluoromethyl-pyridin-3-yl)amino)-thiazole-4-carboxylic acid (2-methyl-pyridin-4-yl)-amide;
2-Methyl-5-(2-methyl-pyridin-3-ylamino)-thiazole-4-carboxylic acid (2-methyl-pyridin-4-yl)-amide;
2-Methyl-5-(pyrazin-2-ylamino)-thiazole-4-carboxylic acid (5-fluoro-pyridin-2-yl)-amide;
5-(5-Chloro-pyridin-3-ylamino)-2-methyl-thiazole-4-carboxylic acid (5-fluoro-pyridin-2-yl)-amide;
2-Methyl-5-(4-methyl-pyridin-2-ylamino)-thiazole-4-carboxylic acid (5-fluoro-pyridin-2-yl)-amide;
2-Methyl-5-(pyrimidin-5-ylamino)-thiazole-4-carboxylic acid (2-chloro-pyridin-4-yl)-amide;
2-Methyl-5-(2-methyl-pyridin-4-ylamino)-thiazole-4-carboxylic acid (5-fluoro-pyridin-2-yl)-amide;
2-Methyl-5-(2-methyl-pyridin-3-ylamino)-thiazole-4-carboxylic acid (2-chloro-pyridin-4-yl)-amide;
2-Methyl-5-(pyrazin-2-ylamino)-thiazole-4-carboxylic acid (2-chloro-pyridin-4-yl)-amide;
5-(5-Chloro-pyridin-3-ylamino)-2-methyl-thiazole-4-carboxylic acid (2-methyl-pyridin-4-yl)-amide;
5-(5-Chloro-pyridin-3-ylamino)-2-methyl-thiazole-4-carboxylic acid (2-chloro-pyridin-4-yl)-amide;
5-(5-Cyano-pyridin-3-ylamino)-2-methyl-thiazole-4-carboxylic acid (5-fluoro-pyridin-2-yl)-amide;
5-(5-Cyano-pyridin-3-ylamino)-2-methyl-thiazole-4-carboxylic acid (2-methyl-pyrimidin-4-yl)-amide;
2-Methyl-5-(4-methyl-pyridin-3-ylamino)-thiazole-4-carboxylic acid (5-fluoro-pyridin-2-yl)-amide;
2-Methyl-5-(pyrimidin-5-ylamino)-thiazole-4-carboxylic acid (2-methyl-pyrimidin-4-yl)-amide;
5-(5-Cyano-pyridin-3-ylamino)-2-methyl-thiazole-4-carboxylic acid (2-methyl-pyridin-4-yl)-amide;
5-(5-Cyano-pyridin-3-ylamino)-2-methyl-thiazole-4-carboxylic acid (4-methyl-pyrimidin-2-yl)-amide;
2-Methyl-5-(4-methyl-pyridin-3-ylamino)-thiazole-4-carboxylic acid (2-chloro-pyridin-4-yl)-amide;
5-(5-Methanesulfonyl-pyridin-3-ylamino)-2-methyl-thiazole-4-carboxylic acid (2-methyl-pyridin-4-yl)-amide;
2-Methyl-5-(6-methyl-pyridazin-4-ylamino)-thiazole-4-carboxylic acid (2-methyl-pyridin-4-yl)-amide;
2-Methyl-5-(6-methyl-pyridazin-4-ylamino)-thiazole-4-carboxylic acid (2-chloro-pyridin-4-yl)-amide;
5-(Isoxazol-3-ylamino)-2-methyl-thiazole-4-carboxylic acid (2-methyl-pyrimidin-4-yl)-amide;
5-(4-Cyano-pyridin-2-ylamino)-2-methyl-thiazole-4-carboxylic acid (2-methyl-pyridin-4-yl)-amide;
5-(2-Chloro-pyridin-4-ylamino)-2-methyl-thiazole-4-carboxylic acid (2-methyl-pyridin-4-yl)-amide;
5-(4-Chloro-pyridin-2-ylamino)-2-methyl-thiazole-4-carboxylic acid (2-methyl-pyrimidin-4-yl)-amide;
2-Methyl-5-(pyrimidin-5-ylamino)-thiazole-4-carboxylic acid (3-chloro-4-fluoro-phenyl)-amide;
5-(5-Methanesulfonyl-pyridin-3-ylamino)-2-methyl-thiazole-4-carboxylic acid (6-fluoro-pyridin-3-yl)-amide;
5-(5-Methanesulfonyl-pyridin-3-ylamino)-2-methyl-thiazole-4-carboxylic acid (2-methyl-pyrimidin-4-yl)-amide;
2-Methyl-5-(pyrimidin-5-ylamino)-thiazole-4-carboxylic acid (4-fluoro-3-methyl-phenyl)-amide;
2-Methyl-5-(pyridin-3-ylamino)-thiazole-4-carboxylic acid (2-ethyl-pyrimidin-4-yl)-amide;
2-Methyl-5-(pyridin-3-ylamino)-thiazole-4-carboxylic acid (5-methyl-4H-[1,2,4]triazol-3-yl)-amide;
and
2-Methyl-5-(pyridin-3-ylamino)-thiazole-4-carboxylic acid (4-methoxymethyl-thiazol-2-yl)-amide.

30 more elements

A compound of 4, selected from the group consisting of:

2-Methyl-5-(5-methyl-pyridin-3-ylamino)-thiazole-4-carboxylic acid (5-fluoro-pyridin-2-yl)-amide;
5-(2-Chloro-pyridin-4-ylamino)-2-methyl-thiazole-4-carboxylic acid (2-methyl-pyrimidin-4-yl)-amide;
5-(5-Methoxy-pyridin-3-ylamino)-2-methyl-thiazole-4-carboxylic acid (2-methyl-pyridin-4-yl)-amide;
2-Methyl-5-(5-methyl-pyridin-3-ylamino)-thiazole-4-carboxylic acid (2-methyl-pyridin-4-yl)-amide;
5-(5-Fluoro-pyridin-3-ylamino)-2-methyl-thiazole-4-carboxylic acid (2-methyl-pyridin-4-yl)-amide;
2-Methyl-5-(2-methyl-2H-pyrazol-3-ylamino)-thiazole-4-carboxylic acid (2-methyl-pyridin-4-yl)-amide;
2-Methyl-5-(pyridin-3-ylamino)-thiazole-4-carboxylic acid (4-methyl-pyrimidin-2-yl)-amide;
2-Methyl-5-(pyridin-2-ylamino)-thiazole-4-carboxylic acid (2-chloro-pyridin-4-yl)-amide;
2-Methyl-5-((5-trifluoromethyl-pyridin-3-yl)amino)-thiazole-4-carboxylic acid (2-methyl-pyridin-4-yl)-amide;
5-(4-Fluoro-pyridin-2-ylamino)-2-methyl-thiazole-4-carboxylic acid (2-methyl-pyridin-4-yl)-amide;
5-(2-Chloro-pyridin-4-ylamino)-2-methyl-thiazole-4-carboxylic acid (2-chloro-pyridin-4-yl)-amide;
5-(5-Hydroxymethyl-pyridin-3-ylamino)-2-methyl-thiazole-4-carboxylic acid (2-methyl-pyridin-4-yl)-amide;
5-(2-Cyano-pyridin-4-ylamino)-2-methyl-thiazole-4-carboxylic acid (2-methyl-pyridin-4-yl)-amide;
2-Methyl-5-(2-methyl-2H-pyrazol-3-ylamino)-thiazole-4-carboxylic acid (2-chloro-pyridin-4-yl)-amide;
5-[2-Methyl-4-(2-methyl-pyridin-4-ylcarbamoyl-thiazol-5-ylamino]-nicotinamide;
2-Methyl-5-(5-sulfamoyl-pyridin-3-ylamino)-thiazole-4-carboxylic acid (2-methyl-pyridin-4-yl)-amide;
5-(5-Fluoro-pyridin-3-ylamino)-2-methyl-thiazole-4-carboxylic acid (2-chloro-pyridin-4-yl)-amide;
5-(5-Fluoro-pyridin-3-ylamino)-2-methyl-thiazole-4-carboxylic acid (4-methyl-thiazol-2-yl)-amide;
5-(5-Fluoro-pyridin-3-ylamino)-2-methyl-thiazole-4-carboxylic acid (2-methyl-pyrimidin-4-yl)-amide;
5-(4-Fluoro-pyridin-2-ylamino)-2-methyl-thiazole-4-carboxylic acid (2-methyl-pyrimidin-4-yl)-amide;
5-(5-Fluoro-pyridin-3-ylamino)-2-methyl-thiazole-4-carboxylic acid (5-fluoro-pyridin-2-yl)-amide;
5-(5-Fluoro-pyridin-3-ylamino)-2-methyl-thiazole-4-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide;
2-Methyl-5-[pyridin-3-ylmethyl)-amino]-thiazole-4-carboxylic acid (2-methyl-pyridin-4-yl)-amide;
2-Methyl-5-(2-methyl-2H-pyrazol-3-ylamino)-thiazole-4-carboxylic acid (2-methyl-pyrimidin-4-yl)-amide;
5-(2-Ethyl-2H-pyrazol-3-ylamino)-2-methyl-thiazole-4-carboxylic acid (2-methyl-pyrimidin-4-yl)-amide;
5-(2,5-Dimethyl-2H-pyrazol-3-ylamino)-2-methyl-thiazole-4-carboxylic acid (2-methyl-pyrimidin-4-yl)-amide;
2-Methyl-5-(1-methyl-1H-pyrazol-4-ylamino)-thiazole-4-carboxylic acid (2-methyl-pyrimidin-4-yl)-amide;
2-Methyl-5-(3-methyl-isoxazol-5-ylamino)-thiazole-4-carboxylic acid (2-methyl-pyrimidin-4-yl)-amide;
2-Methyl-5-(1-methyl-1H-pyrazol-3-ylamino)-thiazole-4-carboxylic acid (2-methyl-pyrimidin-4-yl)-amide;
2-Methyl-5-(1-methyl-1H-pyrazol-4-ylamino)-thiazole-4-carboxylic acid (2-methyl-pyridin-4-yl)-amide;
5-(5-Cyano-pyridin-3-ylamino)-2-methyl-thiazole-4-carboxylic acid (4-methyl-thiazol-2-yl)-amide;
5-(5-Fluoro-pyridin-3-ylamino)-2-methyl-thiazole-4-carboxylic acid (2-methyl-thiazol-4-yl)-amide;
and
5-(2-Chloro-pyridin-4-ylamino)-2-methyl-thiazole-4-carboxylic acid (2-methyl-thiazol-4-yl)-amide.

31 more elements

A compound of 4, selected from the group consisting of:

5-(5-Difluoromethyl-pyridin-3-ylamino)-2-methyl-thiazole-4-carboxylic acid (2-methyl-pyridin-4-yl)-amide;
5-(5-Fluoro-pyridin-3-ylamino)-2-methyl-thiazole-4-carboxylic acid (4-trifluoromethyl-thiazol-2-yl)-amide;
2-Methyl-5-(thiazol-2-ylamino)-thiazole-4-carboxylic acid (2-methyl-pyridin-4-yl)-amide;
5-(5-Chloro-pyridin-3-ylamino)-2-methyl-thiazole-4-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide;
2-Methyl-5-(pyrimidin-5-ylamino)-thiazole-4-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide;
5-(4-Cyano-2-methyl-2H-pyrazol-3-ylamino)-2-methyl-thiazole-4-carboxylic acid (2-methyl-pyridin-4-yl)-amide;
5-(5-Cyclopropyl-2-methyl-2H-pyrazol-3-ylamino)-2-methyl-thiazole-4-carboxylic acid (2-methyl-pyridin-4-yl)-amide;
2-Methyl-5-(2-methyl-2H-pyrazol-3-ylamino)-thiazole-4-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide;
5-(2-Chloro-pyridin-4-ylamino)-2-methyl-thiazole-4-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide;
2-Methyl-5-[2-(2,2,2-trifluoro-ethyl)-2H-pyrazol-3-ylamino]-thiazole-4-carboxylic acid (2-methyl-pyridin-4-yl)-amide;
5-(5-Cyclopropyl-2-methyl-2H-pyrazol-3-ylamino)-2-methyl-thiazole-4-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide;
5-(5-Cyclopropyl-2-methyl-2H-pyrazol-3-ylamino)-2-methyl-thiazole-4-carboxylic acid (4-trifluoromethyl-thiazol-2-yl)-amide;
2-Methyl-5-(2-methyl-5-trifluoromethyl-2H-pyrazol-3-ylamino)-thiazole-4-carboxylic acid (2-methyl-pyridin-4-yl)-amide;
5-(5-Fluoro-pyridin-3-ylamino)-2-methyl-thiazole-4-carboxylic acid (4-cyclopropyl-thiazol-2-yl)-amide;
5-(5-Fluoro-pyridin-3-ylamino)-2-methyl-thiazole-4-carboxylic acid (3-methoxymethyl-phenyl)-amide;
5-(5-Fluoro-pyridin-3-ylamino)-2-methyl-thiazole-4-carboxylic acid [1-(2-methoxy-ethyl)-1H-pyrazol-3-yl]-amide;
2-Methyl-5-(pyridin-3-ylamino)-thiazole-4-carboxylic acid (4-trifluoromethyl-thiazol-2-yl)-amide;
2-Methyl-5-(pyridin-3-ylamino)-thiazole-4-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide;
2-Methyl-5-(pyridin-3-ylamino)-thiazole-4-carboxylic acid [1-(2-methoxy-ethyl)-1H-pyrazol-3-yl]-amide;
2-Methyl-5-(pyridin-3-ylamino)-thiazole-4-carboxylic acid (4-cyclopropyl-thiazol-2-yl)-amide;
2-Methyl-5-(pyridin-3-ylamino)-thiazole-4-carboxylic acid (4-methyl-thiazol-2-yl)-amide;
2-Methyl-5-(pyridin-3-ylamino)-thiazole-4-carboxylic acid thiazol-2-ylamide;
5-(5-Cyclopropyl-2-methyl-2H-pyrazol-3-ylamino)-2-methyl-thiazole-4-carboxylic acid (4-methyl-thiazol-2-yl)-amide;
5-(2-Chloro-pyridin-4-ylamino)-2-methyl-thiazole-4-carboxylic acid (4-methyl-thiazol-2-yl)-amide;
2-Methyl-5-(pyridin-3-ylamino)-thiazole-4-carboxylic acid (5-ethyl-thiazol-2-yl)-amide;
2-Methyl-5-(pyrimidin-5-ylamino)-thiazole-4-carboxylic acid (4-methyl-thiazol-2-yl)-amide;
2-Methyl-5-(1-methyl-1H-pyrazol-4-ylamino)-thiazole-4-carboxylic acid (4-methyl-thiazol-2-yl)-amide;
2-Methyl-5-(pyridin-2-ylamino)-thiazole-4-carboxylic acid (4-methyl-thiazol-2-yl)-amide;
5-(2,5-Dimethyl-2H-pyrazol-3-ylamino)-2-methyl-thiazole-4-carboxylic acid (4-methyl-thiazol-2-yl)-amide;
2-Methyl-5-(1-methyl-1H-pyrazol-3-ylamino)-thiazole-4-carboxylic acid (4-methyl-thiazol-2-yl)-amide;
5-(5-Chloro-pyridin-3-ylamino)-2-methyl-thiazole-4-carboxylic acid (4-methyl-thiazol-2-yl)-amide;
2-Methyl-5-(2-methyl-pyridin-4-ylamino)-thiazole-4-carboxylic acid (4-methyl-thiazol-2-yl)-amide;
and
5-(4-Fluoro-pyridin-2-ylamino)-2-methyl-thiazole-4-carboxylic acid (4-methyl-thiazol-2-yl)-amide.

31 more elements

Dependencies are inferred from the claim text.

Facts

Application: 11/328,879Filed 10 Jan 2006
Priority: EP 0510020314 Jan 2005
Published: US 2006/0160857 A120 Jul 2006
Granted: 16 Mar 2010
Term ends: Not estimatedThe source records don’t support an estimate.

Classification21 codes

C07D 277/42
Nitrogen atoms: amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
A61P 3/00
Drugs for disorders of the metabolism
A61P 3/04
Drugs for disorders of the metabolism: anorexiants; Antiobesity agents
A61P 13/02
Drugs for disorders of the urinary system: of urine or of the urinary tract, e.g. urine acidifiers

Family

US 2006/0160857 A1Pre-grant publication · published 20 Jul 2006
US 7,678,815 B2This patent

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

Timeline

Citations

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