Cinnamide derivatives as KCNQ potassium channel modulators

US6831080B2 · kind B2 · utility

Assignee

• Bristol-Myers Squibb Company · US

Inventors

• Yong-Jin Wu · Madison, US
• Li-Quang Sun · Glastonbury, US
• Jie Chen · Houston, US
• Huan He · Wallingford, US
• Alexandre L'Heureux · Russell, CA
• Pierre Dextraze · Elliot Lake, CA
• Jean-Paul Daris · St-Hubert, CA
• Gene Kinney
• Steven Dworetzky · Middlefield, US
• Piyasena Hewawasam · Middletown, US

Key dates

• Filing date: May 31, 2002
• Grant date: Dec 14, 2004
• Expiry date: Jun 3, 2022

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D491/08
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

There is provided novel cinnamide derivatives of Formula I: wherein R is C1-4 alkyl or trifluoromethyl; R1 is selected from the group consisting of pyridinyl, quinolinyl, thienyl, furanyl, 1,4-benzodioxanyl, 1,3-benzodioxolyl, chromanyl, indanyl, biphenylyl, phenyl and substituted phenyl in which said substituted phenyl is substituted with one or two substituents each independently selected-from the group consisting of halogen, C1-4 alkyl, C1-4 alkoxy, trifluoromethyl, trifluoromethoxy and nitro; R2 and R3 are each independently selected from the group consisting of hydrogen, C1-4 alkyl, and halogen; R4 is selected from the group consisting of di(C1-4 alkyl)amino, trifluoromethoxy and optionally substituted morpholin-4-yl, pyridinyl, pyrimidinyl, piperazinyl, and pyrazinyl with one or two substituents in which said substituent is independently selected from the group consisting of C1-4 alkyl, aminomethyl, hydroxymethyl, chloro or fluoro; R5 is hydrogen, chloro or fluoro; or R4 and R5 taken together are —CH═CH—CH═CH— or —X(CH2)mY— in which X and Y are each independently selected from the group consisting of CH2, (CH2)nN(R9)— and O, where…