Novel acetylenic prostaglandins and processes for the preparation thereof

US4235930A · kind A · utility

Assignee

• Schering A.G. · DE

Inventors

• Werner Skuballa · Berlin, DE
• Bernd Raduchel · Berlin, DE
• Helmut Vorbruggen
• Walter Elger · Berlin, DE
• Olaf Loge
• Ekkehard Schillinger · Berlin, DE

Key dates

• Filing date: Jun 29, 1978
• Grant date: Nov 25, 1980
• Expiry date: Jun 29, 1998

Classification

• Technology area (CPC Y): Emerging Cross-Sectional Technologies
• CPC primary: Y02P20/55
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Prostane derivatives of the formula ##STR1## wherein R.sub.1 is the residue OR.sub.2 and R.sub.2 is hydrogen, alkyl, cycloalkyl, aryl, or a heterocyclic residue; or is NHR.sub.3 wherein R.sub.3 is an acyl group derived from a hydrocarbon carboxylic or sulfonic acid of up to 15 carbon atoms; PA1 A is --CH.sub.2 --CH.sub.2 -- or cis--CH.dbd.CH-- PA1 Z is carbonyl or ##STR2## wherein the OR.sub.4 group can be in the .alpha.- or .beta.-position and R.sub.4 is H or a hydroxy-protective group PA1 X Y is ##STR3## wherein R.sub.4 is as defined above, --CH.sub.2 -- CH.sub.2 -- or --CH.sub.2 --CH-- wherein R.sub.5 is alkyl or 1-5 carbon atoms, if Z is R.sub.5 carbonyl or ##STR4## X Y represents --CH.dbd.CH-- if Z is carbonyl: R.sub.6, R.sub.7, R.sub.8, R.sub.9 and R.sub.10 each independently is hydrogen or an alkyl group of 1-5 carbon atoms; and PA1 R.sub.11 is alkyl of 1-5 carbon atoms; PA1 and if R.sub.2 is hydrogen, the salts thereof with physiologically compatible bases are prostaglandins having prolonged duration of activity and increased selectivity of effectiveness.