Process for preparing a 2-(2-amino-1, 6-dihydro-6-oxo-purin-9-yl)methoxy-1,3-propanediol derivative

US6340756B1 · kind B1 · utility

Assignee

• Syntex (U.S.A.) LLC · US

Inventors

• Charles Alois Dvorak · Palo Alto, US
• Douglas L. Wren · Palo Alto, US
• Lawrence Emerson Fisher · Mountain View, US
• Steven D. Axt · San Jose, US
• Eric R. Humphreys · San Bruno, US
• Humberto B. Arzeno · Cupertino, US
• Colin C. Beard · Saratoga, US
• Sam Linh Nguyen · Denver, US
• Yeun-Kwei Han · Louisville, US
• Christopher Roberts · Berthoud, US
• Jan P. Lund · Boulder, US
• Paul R. Fatheree · San Francisco, US

Key dates

• Filing date: Feb 3, 2000
• Grant date: Jan 22, 2002
• Expiry date: Feb 3, 2020

Classification

• Technology area (CPC Y): Emerging Cross-Sectional Technologies
• CPC primary: Y02P20/55
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

wherein Z1 is hydrogen or an amino-protecting group selected from the group consisting of acyl of the formula R—C(O)—, wherein R is alkyl of 1-6 carbon atoms; trityl, optionally substituted with methoxy; and N-(9-fluorenylmethoxycarbonyl); Y1 is halo, aralkyloxy or acyloxy, wherein acyl is as defined above; and Y2 is aralkyloxy. These intermediates are useful in a novel process for preparing the mono-L-valine ester of 2-(2-amino-1,6-dihydro-6-oxo-purin-9-yl) methoxy-1,3-propanediol (ganciclovir). The mono-L-valine ester of ganciclovir and its pharmaceutically acceptable salts are of value as antiviral agents with improved absorption.