US 7,259,266 B2Granted

Benzopyran compounds useful for treating inflammatory conditions

AssigneePharmacia Corporation

InventorsJeffry Carter, David Brown, Li Xing, Karl Aston, John Springer, Francis Koszyk, Steven Kramer, Renee Huff, Yi Yu, Bruce Hamper, Subo Laio, Angela Deprow, Teresa Fletcher, E. Ann Hallinan, James Kiefer, David Limburg, Lijuan Wang, Cindy Ludwig, John McCall, John Talley

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Abstract

The subject invention concerns methods and compounds that have utility in the treatment of a condition associated with cyclooxygenase-2 mediated disorders. Compounds of particular interest are benzopyrans and their analogs defined by formula 1 Wherein Z, X, R1, R2, R3, and R4 are as described in the specification.

The compound selected from the group consisting of

(2R)-6-chloro-7-isobutyl-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid;
6-chloro-7-isobutyl-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid;
(2R)-7-benzyl-6-chloro-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid;
7-benzyl-6-chloro-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid;
7-butoxy-6-chloro-8-methyl-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid;
7-benzyl-6-bromo-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid;
7-butyl-6-chloro-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid;
6,8-dichloro-7-(2-ethylbutoxy)-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid;
6-chloro-8-methyl-7-propoxy-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid;
6-chloro-7-(isobutylthio)-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid;
6-chloro-7-(2-ethylbutoxy)-8-methyl-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid;
6-chloro-7-(isopentyloxy)-8-methyl-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid;
8-methyl-6-(trifluoromethoxy)-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid;
6,8-dichloro-7-isobutoxy-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid;
7-benzyl-6-methyl-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid;
7-(sec-butylthio)-6-chloro-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid;
(2S)-6-ethyl-8-methyl-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid;
6-chloro-8-(4-chloro-3-methylphenyl)-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid;
8-ethyl-6-(trifluoromethoxy)-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid;
(2S)-8-ethyl-6-(trifluoromethoxy)-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid;
(2S)-6-chloro-5,7-dimethyl-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid
6-chloro-8-(4-methylphenyl)-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid;
6-chloro-8-(3-fluoro-4-methylphenyl)-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid;
8-propyl-6-(trifluoromethoxy)-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid;
5-bromo-6,7-dichloro-8-methoxy-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid;
6-chloro-8-(4-ethylphenyl)-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid;
and
(2S)-6,8-dimethyl-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid;
or their isomer and pharmaceutically acceptable salt thereof.

26 more elements

Facts

Application

10/801,429Filed 16 Mar 2004 · us provisional application

Priority

31 Mar 2003

Published

US 2005/0148777 A17 Jul 2005

Granted

21 Aug 2007

Term ends

Not estimatedThe source records don’t support an estimate.

Classification34 codes

C07D 311/58
Benzo[b]pyrans, not hydrogenated in the carbocyclic ring: other than with oxygen or sulphur atoms in position 2 or 4
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 1/16
Drugs for disorders of the alimentary tract or the digestive system: for liver or gallbladder disorders, e.g. hepatoprotective agents,…
A61P 9/00
Drugs for disorders of the cardiovascular system

Abstract

Claims1