NOUVEAUX DERIVES DE LA CLASSE DES PROSTAGLANDINES ET LEUR PREPARATION

1386870 Prostaglandins UPJOHN CO 16 Feb 1972 [11 March 1971] 7171/72 Heading C2C [Also in Divisions C3 and A5] The invention comprises optically active compounds of the formulae or racemates thereof, wherein R 1 is H or C 1-8 alkyl, and R 2 and R 3 are H, methyl or ethyl, provided that at least one of R 2 and R 3 is not H, and pharmacologically acceptable salts thereof and their preparation. The 16-alkyl and 16,16-dialkyl PGF 1# compounds are obtained by reducing the corresponding 16-alkyl and 66,16-dialkyl PGE 1 compounds and separating the 9# hydroxy isomer and the 16-alkyl and 16,16-dialkyl PGA 1 and PGB 1 compounds are prepared by dehydrating the corresponding 16-alkyl and 16,16-dialkyl PGE 1 compounds, followed by, if desired, hydrolysis of any resulting esters or esterification of any resulting acids. The following intermediates and starting materials are prepared: 6 - (3 - methyl - cis - 1 - heptenyl)bicyclo [3,1,0]hexan - 3 - one; 7 - [6 - (3 - methyl - cis- 1 - heptenyl) - 3 - oxo - bicyclo[3,1,0]hex - 2α- yl] - heptanoic acid and its methyl and 2,2,2-trichloroethyl esters; methyl 7-[6-(1,2- dihydroxy - 3 - methylheptyl) - 3 - oxobicyclo- [3,1,0]hex - 2α - yl] - heptanoate and its bis - (methane - sulphonate; 16-methyl-PGE 1 , 16,16-dimethyl-PGE 1 , 16-ethyl-PGE 1 , 16-ethyl 16-methyl-PGE 1 , and 16,16-diethyl-PGE 1 , and their methyl and 2,2,2-trichloroethyl esters; 7 - [3 - hydroxy - 6 - (3 - methyl - cis - 1-heptenyl)bicyclo[3,1,0)- hex - 2α - yl]heptanoic acid and its methyl ester; 7-{6-[3-methyl-(or 3,3- dimethyl-, or 3,3-diethyl-, or 3-ethyl-, or 3 - ethyl - 3 - methyl) - cis - 1 - heptenyl) - 3- oxobicyclo[3,1,0]hex-2α-yl}heptanoates.