Key intermediates in the manufacture of simvastatin

US5763653A · kind A · utility

Assignee

• RANBAXY LABORATORIES LIMITED · IN

Inventors

• Jag Mohan Khanna · New Delhi, IN
• Yatendra Kumar · Barwala, IN
• Rajesh Kumar Thaper · Jammu, IN
• Satyananda Misra · New Delhi, IN
• S. M. Dileep Kumar · New Delhi, IN

Key dates

• Filing date: Mar 13, 1997
• Grant date: Jun 9, 1998
• Expiry date: Mar 13, 2017

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C2602/28
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

A process for preparing simvastatin from lovastatin or mevinolinic acid in salt form comprises treating either starting material with cyclopropyl or butyl amine, the pyranone ring thereby being opened when lovastatin is the starting material, adding a methyl group to the 2-methylbutyrate side chain, and thereafter closing the open pyranone ring to produce simvastatin. The process is performed without protecting and deprotecting the two hydroxy groups of the open pyranone ring. In a preferred embodiment, the starting material is treated with cyclopropyl amine which produces simvastatin via the novel intermediate lovastatin cyclopropyl amide.