Methods for synthesis of prodrugs from 1-acyl-alkyl derivatives and compositions thereof

US6927036B2 · kind B2 · utility

Assignee

• Xero Port, Inc. · US

Inventors

• Mark A. Gallop · Santa Clara, US
• Jia-Ning Xiang · Palo Alto, US
• Fenmei Yao · Mountain View, US
• Laxminarayan Bhat · Bengaluru, IN
• Cindy X. Zhou · Palo Alto, US

Key dates

• Filing date: Jun 11, 2002
• Grant date: Aug 9, 2005
• Expiry date: Jul 3, 2022

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C2601/14
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Disclosed is a method for synthesizing 1-(acyloxy)-alkyl derivatives of primary or secondary amine drugs from 1-acyl-alkyl derivatives of primary or secondary amine drugs, which typically proceeds stereospecifically, in high yield, does not require the use of activated intermediates and/or toxic compounds and is readily amenable to scale-up. For example, 1-acyl-alkyl derivatives of gabapentin and pregabalin are oxidized to yield 1-(acyloxy)-alkyl derivatives of gabapentin and pregabalin, respectively.