GB1302349A - - Google Patents

Abstract

1302349 Prostaglandins UPJOHN CO 12 Aug 1971 [15 Sept 1970] 37934/71 Heading C2C The invention comprises novel prostaglandins of the formulµ or racemic compounds of these formulae and the mirror images thereof, wherein R 3 is H or C 1-8 alkyl, and R 4 is H, formyl or C 2-8 alkanoyl, and salts thereof when R 3 is H. Compounds of the Formulµ XIV, XV, XVIII and XIX in which R 4 is H are prepared by isomerizing PGE 2 , PGF 2 α, PGF 2# , 15#-PGE 2 , 15#-PGF 2 α or 15#- PGF 2 # or esters thereof by exposing solution of said PGE and PGF reactants and diaryl sulphides or diaryl disulphides to ultraviolet radiation in the range 3000 to 5000 A‹. 5,6-Trans-PGF 2 and 5,6-trans-15#-PGF 2 or esters thereof may also be prepared by ring carbonyl reduction of 5,6-trans-PGE 2 and 5,6-trans-15#-PGE 2 or esters thereof. Compounds of Formulµ XVI and XX in which R 4 is H are made by the neutral or acidic dehydration of 5,6-trans-PGE 2 and 5,6- trans-15#-PGE 2 or esters thereof. Compounds of the Formulµ XVII and XXI in which R 4 is H are obtained by reacting 5,6-trans-PGE 2 or 5,6-trans-PGA 2 or the corresponding 15# isomers thereof or esters thereof with bases whose water solutions have pHs greater than 10. The free hydroxy groups in the compounds thus obtained may, if desired, be acylated, and any free carboxy groups esterified. 5,6-Trans-15#- PGA 2 may also be obtained by extracting colonies or colony pieces of the marine invertebrate Plexaura homomella (Esper), 1972, forma R. Pharmaceutical compositions, suitable for oral, parenteral, rectal, or topical administration, contain the above novel compounds or salts thereof, in admixture with pharmaceuticallyacceptable carriers. The compounds possess the usual prostaglandin type of activities.