9-halo-2-prostaglandin derivatives, processes for the preparation thereof and use thereof as medicinal agents

US4699920A · kind A · utility

Assignee

• SCHERING CORPORATION · US

Inventors

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

Key dates

• Filing date: Sep 17, 1985
• Grant date: Oct 13, 1987
• Expiry date: Sep 17, 2005

Classification

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

Abstract

The invention relates to 9-halo-.DELTA..sup.2 -prostane derivatives of general Formula I ##STR1## wherein Hal is a fluorine or chlorine atom in the .alpha.- or .beta.-position, PA1 R.sub.1 is the residue OR.sub.2 with R.sub.2 meaning a hydrogen atom, alkyl, cycloalkyl, aryl or a heterocyclic residue; or the residue NHR.sub.3 wherein R.sub.3 means an acid residue or the residue R.sub.2 and PA1 A is a --CH.sub.2 --CH.sub.2 -- or cis-CH.dbd.CH--group, PA1 B is a --CH.sub.2 --CH.sub.2 -- or trans--CH.dbd.CH-- or --C.tbd.C--group, PA1 W is a free or functionally modified hydroxymethylene or ##STR2## wherein the respective OH-groups can be in the .alpha.- or .beta.-position, PA1 D and E jointly mean a direct bond or PA1 D is a straight- or branched-chain alkylene group of 1-10 carbon atoms, which can optionally be substituted by fluorine atoms, PA1 E is an oxygen or sulfur atom, a direct bond, a --C.tbd.C--bond or a --CR.sub.6 .dbd.CR.sub.7 --group wherein R.sub.6 is a hydrogen atom or an alkyl group and R.sub.7 is a hydrogen atom, an alkyl group or a halogen atom, PA1 R.sub.4 is a free or functionally modified hydroxy group, PA1 R.sub.5 is a hydrogen atom, an alkyl group, a halogen-subs…