Process for manufacturing simvastatin and the novel intermediates

US6573392B1 · kind B1 · utility

Assignee

• Biocon India Limited · IN

Inventors

• Ganesh Sambasivam · Bengaluru, IN
• Madhavan Sridharan · Savanuru, IN
• Poornaprajna Acharya · Savanuru, IN
• Joy Mathew · Savanuru, IN

Key dates

• Filing date: May 10, 2002
• Grant date: Jun 3, 2003
• Expiry date: May 10, 2022

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D309/30
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

This invention describes the synthesis of simvastatin from lovastatin by converting the lovastatin to lova amide using a secondary amine and subsequent reaction with a metal amide base generated from n-butyl lithium and pyrrolidine and followed by treatment with methyl iodide to give desired C-methylated intermediate. This intermediate was further transformed to the final product, simvastatin. This method of production consumes lesser quantities of metal amide, gives fewer side reactions and a lowered overall cost of manufacture of simvastatin than other procedures reported.