IP Library › Granted Patent US 7,935,715

Granted Patent B2

US 7,935,715 · App. 11/781,336 · Granted May 3, 2011

Compounds which modulate the CB2 receptor

Assignee: Boehringer Ingelheim International GmbH

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Quick Facts

Patent No.: US 7,935,715
App. No.: 11/781,336
Granted: May 3, 2011
Kind: B2

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Abstract

Compound of formula (I) are disclosed. Compounds according to the invention bind to and are agonists, antagonists or inverse agonists of the CB2 receptor, and are useful for treating inflammation. Those compounds which are agonists are additionally useful for treating pain.

Claims (109)

1. A compound chosen from

2-Methyl-N-pyridin-3-yl-2-(4-trifluoromethyl-benzenesulfonyl)-propionamide

2-(4-Chloro-benzenesulfonyl)-2-methyl-N-(4-methyl-pyridin-2-yl)-propionamide

2-(4-Chloro-benzenesulfonyl)-2-methyl-N-(5-methyl-pyridin-2-yl)-propionamide

2-(4-Chloro-benzenesulfonyl)-2-methyl-N-(6-methyl-pyridin-2-yl)-propionamide

2-(4-Chloro-benzenesulfonyl)-2-methyl-N-(5-trifluoromethyl-pyridin-2-yl)-propionamide

2-(4-Chloro-benzenesulfonyl)-2-methyl-N-(4-trifluoromethyl-pyridin-2-yl)-propionamide

2-(4-Chloro-benzenesulfonyl)-N-(4-ethyl-pyridin-2-yl)-2-methyl-propionamide

2-(4-Chloro-benzenesulfonyl)-2-methyl-N-(5-phenyl-pyridin-2-yl)-propionamide

2-(4-Chloro-benzenesulfonyl)-2-methyl-N-(6-trifluoromethyl-pyridin-2-yl)-propionamide

2-(4-Chloro-benzenesulfonyl)-N-(6-methoxy-pyridin-3-yl)-2-methyl-propionamide

2-(4-Chloro-benzenesulfonyl)-2-methyl-N-pyridin-3-yl-propionamide

2-(4-Chloro-benzenesulfonyl)-2-methyl-N-(6-phenoxy-pyridin-3-yl)-propionamide

2-(4-Chloro-benzenesulfonyl)-2-methyl-N-(3-trifluoromethyl-pyridin-2-yl)-propionamide

2-(4-Chloro-benzenesulfonyl)-2-methyl-N-pyridin-2-yl-propionamide

2-Methyl-2-(4-trifluoromethyl-benzenesulfonyl)-N-(5-trifluoromethyl-pyridin-2-yl)-propionamide

3-Methyl-2-(4-trifluoromethyl-benzenesulfonyl)-N-(5-trifluoromethyl-pyridin-2-yl)-butyramide

2-(4-Bromo-benzenesulfonyl)-2-methyl-N-(5-trifluoromethyl-pyridin-2-yl)-propionamide

2-(3-Fluoro-4-methoxy-benzenesulfonyl)-2-methyl-N-(5-trifluoromethyl-pyridin-2-yl)-propionamide

2-(4-Bromo-benzenesulfonyl)-2-methyl-N-(6-trifluoromethyl-pyridin-2-yl)-propionamide

2-(3-Fluoro-4-methoxy-benzenesulfonyl)-2-methyl-N-(6-trifluoromethyl-pyridin-2-yl)-propionamide

2-(3-Fluoro-4-methyl-benzenesulfonyl)-2-methyl-N-(6-trifluoromethyl-pyridin-2-yl)-propionamide

3-Methyl-2-(4-trifluoromethyl-benzenesulfonyl)-N-(6-trifluoromethyl-pyridin-2-yl)-butyramide

2-(4-Cyano-benzenesulfonyl)-2-methyl-N-(5-trifluoromethyl-pyridin-2-yl)-propionamide

2-(3-Fluoro-4-methyl-benzenesulfonyl)-2-methyl-N-(5-trifluoromethyl-pyridin-2-yl)-propionamide

4-(4-Trifluoromethyl-benzenesulfonyl)-tetrahydro-pyran-4-carboxylic acid (6-trifluoromethyl-pyridin-2-yl)-amide

1-(4-Trifluoromethyl-benzenesulfonyl)-cyclopropanecarboxylic acid (4-trifluoromethyl-pyridin-2-yl)-amide

1-(4-Trifluoromethyl-benzenesulfonyl)-cyclopropanecarboxylic acid (5-trifluoromethyl-pyridin-2-yl)-amide

1-(4-Trifluoromethyl-benzenesulfonyl)-cyclopropanecarboxylic acid (6-trifluoromethyl-pyridin-2-yl)-amide

2-Methyl-2-(toluene-4-sulfonyl)-N-(6-trifluoromethyl-pyridin-2-yl)-propionamide

2-Methyl-2-(toluene-4-sulfonyl)-N-(5-trifluoromethyl-pyridin-2-yl)-propionamide

2-Benzenesulfonyl-2-methyl-N-(6-trifluoromethyl-pyridin-2-yl)-propionamide

2-Benzenesulfonyl-2-methyl-N-(5-trifluoromethyl-pyridin-2-yl)-propionamide

1-(4-Chloro-benzenesulfonyl)-cyclopropanecarboxylic acid (5-trifluoromethyl-pyridin-2-yl)-amide

1-(4-Chloro-benzenesulfonyl)-cyclopropanecarboxylic acid (4-trifluoromethyl-pyridin-2-yl)-amide

2-(3-Fluoro-benzenesulfonyl)-2-methyl-N-(5-trifluoromethyl-pyridin-2-yl)-propionamide

2-(2-Fluoro-benzenesulfonyl)-2-methyl-N-(5-trifluoromethyl-pyridin-2-yl)-propionamide

2-(4-Chloro-2-fluoro-benzenesulfonyl)-2-methyl-N-(5-trifluoromethyl-pyridin-2-yl)-propionamide

2-(4-Chloro-2-fluoro-benzenesulfonyl)-2-methyl-N-(6-trifluoromethyl-pyridin-2-yl)-propionamide

2-(4-Chloro-2-fluoro-benzenesulfonyl)-2-methyl-N-(4-trifluoromethyl-pyridin-2-yl)-propionamide

2-(2-Fluoro-4-methyl-benzenesulfonyl)-2-methyl-N-(5-trifluoromethyl-pyridin-2-yl)-propionamide

2-(4-Cyano-2-fluoro-benzenesulfonyl)-2-methyl-N-(5-trifluoromethyl-pyridin-2-yl)-propionamide

2-(4-Fluoro-benzenesulfonyl)-2-methyl-N-(5-trifluoromethyl-pyridin-2-yl)-propionamide

2-(4-Fluoro-benzenesulfonyl)-2-methyl-N-(6-trifluoromethyl-pyridin-2-yl)-propionamide

2-(2,5-Difluoro-benzenesulfonyl)-2-methyl-N-(5-trifluoromethyl-pyridin-2-yl)-propionamide

2-(2,5-Difluoro-benzenesulfonyl)-2-methyl-N-(6-trifluoromethyl-pyridin-2-yl)-propionamide

N-(5-sec-Butyl-pyridin-2-yl)-2-(4-chloro-benzenesulfonyl)-2-methyl-propionamide

2-(4-Methanesulfonyl-benzenesulfonyl)-2-methyl-N-(5-methyl-pyridin-2-yl)-propionamide

2-[(4-methoxyphenyl)sulfonyl]-2-methyl-N-[6-(trifluoromethyl)pyridin-2-yl]propanamide

2-[(2,4-difluorophenyl)sulfonyl]-2-methyl-N-[5-(trifluoromethyl)pyridin-2-yl]propanamide

2-[(2,4-difluorophenyl)sulfonyl]-2-methyl-N-[4-(trifluoromethyl)pyridin-2-yl]propanamide

2-[(2,4-difluorophenyl)sulfonyl]-2-methyl-N-[6-(trifluoromethyl )pyridin-2-yl]propanamide

2-methyl-2-{[4-(methylsulfonyl)phenyl]sulfonyl}-N-[5-(trifluoromethyl)pyridin-2-yl]propanamide

2-methyl-2-{[4-(methylsulfonyl)phenyl]sulfonyl}-N-[4-(trifluoromethyl)pyridin-2-yl]propanamide

N-(4-ethylpyridin-2-yl)-2-methyl-2-{[4-(methylsulfonyl)phenyl]sulfonyl}propanamide

2-methyl-2-{[4-(methylsulfonyl)phenyl]sulfonyl}-N-[6-(trifluoromethyl)pyridin-2-yl]propanamide

2-[(4-chloro-2-fluorophenyl)sulfonyl]-N-(4-ethylpyridin-2-yl)-2-methylpropanamide

2-[(4-chloro-2-fluorophenyl)sulfonyl]-2-methyl-N-(5-methylpyridin-2-yl)propanamide

2-methyl-N-[3-(trifluoromethyl)phenyl]-2-{[6-(trifluoromethyl)pyridin-3-yl]sulfonyl}propanamide

N-(4-tert-butylphenyl)-2-methyl-2-{[6-(trifluoromethyl)pyridin-3 -yl]sulfonyl}propanamide

2-methyl-N-[4-(trifluoromethyl)phenyl]-2-{[6-(trifluoromethyl)pyridin-3-yl]sulfonyl}propanamide

N-(3-tert-butylphenyl)-2-methyl-2-{[6-(trifluoromethyl)pyridin-3 -yl]sulfonyl}propanamide and

N-(2-tert-butylpyridin-4-yl)-2-[(4-chlorophenyl)sulfonyl]-2-methylpropanamide

or a tautomer or pharmaceutically acceptable salt thereof.

2. A compound chosen from