Method for producing 3-amidinophenylalanine derivatives

US8088921B2 · kind B2 · utility

Assignee

• Wilex AG · DE

Inventors

• Hugo Ziegler · Witterswil, CH
• Peter Wikstroem · Oberwil, CH

Key dates

• Filing date: Oct 15, 2010
• Grant date: Jan 3, 2012
• Expiry date: Oct 15, 2030

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D211/60
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The present invention describes a method for the synthesis of enantiomerically pure 3-amidinophenylalanine derivatives, which are used as pharmaceutically effective urokinase inhibitors, by starting from 3-cyanophenylalanine derivatives. The methods of manufacture comprising only one synthesis step lead to new intermediates, namely 3-hydroxyamidino- and 3-amidrazonophenylalanine derivatives. These intermediates or their acetyl derivatives can be reduced into the desired 3-amidino-phenylalanine derivatives under gentle conditions (H2 or ammonium formiate, Pd/C (approx. 10%), ethanol/water, room temperature, normal pressure or also H2, Pd/C, AcOH or HCl/ethanol, 1-3 bar) in excellent yields and in an enantiomeric excess of up to 99.9%.