Novel acetylenic prostaglandin analogs

US4073934A · kind A · utility

Assignee

• SCHERING CORPORATION · US

Inventors

• Werner Skuballa · Berlin, DE
• Bernd Raduechel · Berlin, DE
• Helmut Vorbrueggen · Berlin, DE
• Walter Elger · Berlin, DE
• Olaf Loge
• Eckehard Schillinger · Berlin, DE

Key dates

• Filing date: Apr 16, 1976
• Grant date: Feb 14, 1978
• Expiry date: Apr 16, 1996

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C405/00
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Optically active and racemic prostaglandin derivatives of the formula ##STR1## wherein R.sub.1 is --OR.sub.5 ; --NHSO.sub.2 CH.sub.3 ; or --O--CH.sub.2 --U--V; R.sub.5 is hydrogen, alkyl, aryl, or a heterocyclic group; U is a direct bond, carbonyl or carbonyloxy; and V is phenyl substituted by 1-3 phenyl, alkoxy of 1-2 carbon atoms, or halogen, preferably bromine; R.sub.2 is hydrogen or alkyl of 1-5 carbon atoms; R.sub.3 is alkyl, substituted or unsubstituted cycloalkyl, straight-chain or branched alkyl of 1-5 carbon atoms substituted by aryl or substituted aryl, when R.sub.1 is as above; or R.sub.3 is aryl or substituted aryl group when R.sub.1 is --OR.sub.5 ', --NHSO.sub.2 CH.sub.3, or --O--CH.sub.2 --U--V and R.sub.5 ' is aryl or a heterocyclic group and U and V are as above; R.sub.4 is hydrogen or an ether or acyl residue; A is --CH.sub.2 --CH.sub.2 -- or cis--CH.dbd.CH--; B is --CH.sub.2 --CH.sub.2 -- or trans--CH.dbd.CH--; D is a direct bond, oxygen, or sulfur; Z is carbonyl or >CH OR.sub.4 wherein OR.sub.4 is in the .alpha.- or .beta.-position; and X y is ##STR2## when Z is >CH OR.sub.4 --, or ##STR3## or --CH.dbd.CH-- when Z is carbonyl; AND, WHEN R.sub.1 is hydroxy, the ph…