CIS 3,4-dihydroxy-2-(3-methylbutanoyl)-5-(3-methylbutyl)-4-(4-methylpentanoyl)cyclopent-2-en-1-derivatives, substantially enantiomerically pure compositions and methods

US8410178B2 · kind B2 · utility

Assignee

• KinDex Therapeutics, LLC · US

Inventors

• Brian J. Carroll · Gig Harbor, US
• Gary Darland · Port Orchard, US
• Anuradha Desai · Gig Harbor, US
• Veera Konda · Bellevue, US
• Clinton J. Dahlberg · Port Orchard, US
• Jan Urban · San Diego, US

Key dates

• Filing date: Oct 28, 2011
• Grant date: Apr 2, 2013
• Expiry date: Oct 28, 2031

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07B2200/13
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

The present application provides cis 3,4-dihydroxy-2-(3-methylbutanoyl)-5-(3-methylbutyl)-4-(4-methylpentanoyl)cyclopent-2-en-1-one derivatives and substantially enantiomerically pure compositions thereof. These derivatives include (+)-(4S,5R)-3,4-dihydroxy-2-(3-methylbutanoyl)-5-(3-methylbutyl)-4-(4-methylpentanoyl)cyclopent-2-en-1-one, (−)-(4R,5S)-3,4-dihydroxy-2-(3-methylbutanoyl)-5-(3-methylbutyl)-4-(4-methylpentanoyl)cyclopent-2-en-1-one, and salts and crystals thereof. The application further provides methods of using the disclosed compounds and compositions to activate PPARγ, activate GPR120, inhibit inflammation, and treat conditions responsive to PPARγ modulation, conditions responsive to GPR120 modulation, and metabolic disturbances such as diabetes.