GB1314291A - Prostaglandins and the preparation thereof - Google Patents

Abstract

1314291 Prostaglandin derivatives UPJOHN CO 4 May 1971 [4 May 1970 (2) 14 May 1970 (2)] 12898/71 Heading C2C The invention comprises novel prostaglandin derivatives of the formulµ wherein R 1 is H, C 1-8 alkyl or a pharmacologically acceptable cation, R 2 is CH 3 or CH 3 CH 2 , A is and X is trans-CH=CH- or -CH 2 CH 2 - and Y and Z are both -CH 2 CH 2 -, or X is trans -CH=CH, Y is cis-CH=CH-, and Z is -CH 2 CH 2 - or cis-CH=CH, provided that R 2 is CH 3 CH 2 when A is O or X is trans-CH=CH-, Y and Z are both -CH 2 CH 2 - and the 15-OH group is the S configuration, and processes for preparing these compounds and those in which R 2 is CH 3 , A is O or X is trans-CH=CH- and Y and Z are both -CH 2 CH 2 - and the 15-OH group is in the R configuration. Compounds of the above formulµ in which A is are prepared by reacting compounds of the formula wherein A<SP>1</SP> is C 1-4 alkyl, phenyl optionally substituted with 1 or 2 fluorine or chlorine atoms or C 1-4 alkyl or C 7-12 aralkyl and wherein R 3 is C 1-8 alkyl or Si(A) 3 with compounds of the formula R 2 MgX, wherein X is Cl, Br or I and hydrolysing the resulting product. Compounds of the above formula in which A is =O are obtained by oxidizing the corresponding compounds in which A is with a reagent which selectively oxidizes secondary OH to = O in the presence of carboncarbon double bonds. Pharmaceutical compositions, suitable for orals parenteral, buccal, sublingual or topical adminis, tration, contain the above novel compoundtogether with pharmaceutically acceptable carriers. The compounds possess prostaglandin like activities.