Process for the preparation of enantiomerically pure cycloalkano-indol -and azaindol -and pyrimido 1,2a! indolcarboxcyclic acids and their activated derivatives

US5952498A · kind A · utility

Assignee

• BAYER HEALTHCARE LLC · DE

Inventors

• Jan-Bernd Lenfers · Wuppertal, DE
• Peter Fey · Wuppertal, DE
• Paul Naab · Bad Reichenhall, DE
• Kai van Laak · Recklinghausen, DE

Key dates

• Filing date: Mar 31, 1997
• Grant date: Sep 14, 1999
• Expiry date: Mar 31, 2017

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D487/04
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The invention relates to a process and intermediates for the preparation of enantiomerically pure cycloalkanoindolecarboxylic acids and azaindolecarboxylic acids and pyrimido1,2a!indolecarboxylic acids and their activated derivatives, characterized in that the tolyl acetic acid is first esterified with a chiral alcohol, then diastereoselective substitution at .alpha.-carbon atoms is carried out and this product is halogenated in the tolyl group and then reacted with appropriate cycloalkanoindoles, cycloalkanoazaindoles or pyrimido1,2a!indoles. It is possible by this method to prepare specifically, in high purity, the enantiomerically pure carboxylic acids which are intermediates for valuable medicaments.