Process for the preparation of optically-active carbazole derivatives, new R- and S-carbazole derivatives and pharmaceutical compositions containing these compounds

US4985454A · kind A · utility

Assignee

• Boehringer Mannheim GmbH · DE

Inventor

• Herbert Leinert · Heppenheim, DE

Key dates

• Filing date: Jan 19, 1989
• Grant date: Jan 15, 1991
• Expiry date: Jan 19, 2009

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D317/20
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

A process for the preparation of S- or R-carbazole derivatives of the general formula: ##STR1## in which R is an unsubstituted or substituted amino radical and pharmacologically acceptable salts, by either reacting R-(-)-epichlorohydrin (for the S-carbazole derivative); or reacting an S-epoxide derivative of the general formula: ##STR2## in which R.sub.1 is the residue of a substituted sulphonic acid derivative (for the R-carbazole derivative); with 4-hydroxycarbazole and then with ammonia or a substituted amine of the general formula RH, and recovering the compound or converting it to a pharmacologically acceptable salt. The new R-(+)- and S(-)-carbazole derivatives provided by the inventive process have unexpected beta blocking and vasodilatory properties and are useful in pharmaceutical compositions. R-(+)-carbazole derivatives are also useful for the treatment of glaucoma.