Methods and intermediates for the preparation of (4bS,5aR)-12-cyclohexyl-N-(N,N-dimethylsulfamoyl)-3-methoxy-5a-((1R,5S)-3-methyl-3,8-diazabicyclo [3.2.1]octane-8-carbonyl)-4b,5,5a,6-tetrahydrobenzo [3,4]cyclopropa[5,6]azepino[1,2-A]indole-9-carboxamide

US9556204B2 · kind B2 · utility

Assignee

• Bristol-Myers Squibb Company · US

Inventors

• Albert J. DelMonte · Princeton, US
• Kenneth J. Natalie, Jr. · Baltimore, US
• Kenneth Joseph FRAUNHOFFER · Princeton, US
• Christina Ann Risatti · Princeton, US
• Chao Hang · Monmouth Junction, US
• Zhinong Gao · Monmouth Junction, US
• Akin H. Davulcu · Wilmington, US
• Wenhao Hu · New Brunswick, US

Key dates

• Filing date: Jul 16, 2013
• Grant date: Jan 31, 2017
• Expiry date: Aug 25, 2033

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D487/04
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The present invention provides methods and intermediates for the preparation of (1aR,12bS)-8-cyclohexyl-11-fluoro-N-((1-methylcyclopropyl)sulfonyl)-1a-((3-methyl-3,8-diazabicyclo[3.2.1]oct-8-yl)carbonyl)-1,1a,2,12b-tetrahydrocyclopropa[d]indolo[2,1-a][2]benzazepine-5-carboxamide (formula I), including pharmaceutically acceptable salts. The compound has activity against hepatitis C virus (HCV) and may be useful in treating those infected with HCV.