Novel Gona-1,3,5(10)-Trienes, processes for their preparation, and compositions incorporating them

摘要

1,152,226. 11 - Alkoxy - 13 - alkyl - gonatrienes. ROUSSEL-UCLAF. 1 June, 1967 [7 Sept., 1966; 9 Dec., 1966; 28 Feb., 1967; 9 March, 1967], No. 25315/67. Heading C2U Novel compounds of formula (wherein A and E are each selected from hydrogen, C 1-4 alkyl and C 1-18 carboxylic acyl, B and B1 are C 1-4 alkyl, and R is substituted or unsubstituted saturated or unsaturated hydrocarbon group), and derivatives thereof containing one or more additional nuclear substituents, are prepared (a) from the corresponding 11# - alkoxy - 13# - alkyl - 17α- saturated hydrocarbon - 17#- hydroxy - gona - 4,9 - dien-3-one by catalytic isomerization (e.g. using palladium hydroxide as catalyst) or (b) from the corresponding 3-hydroxy-11#-alkoxy-13#-alkylgona-1,3,5(10)-trien-17-one by reaction with an appropriate R-organometallic compound, in each case to obtain a 3,17#-dihydroxy compound of Formula I which is optionally subjected to 3- or 3,17-esterification or etherification, or reduction of a l7α-alkynyl group to alkenyl. 11#- Methoxy - 17α- methyl - 17# - hydroxy - estra-4,9-dien-3-one is prepared from the corresponding 11#-ol which in turn is obtained from 17α- methyl - 17#- hydroxy - estra - 5(10),9(11)- dien-3-one via 11#-hydroperoxy-17α-methyl-17#- hydroxy-ester-4,9-dien-3-one. Pharmaceutical compositions suitable for oral, perlingual, transcutaneous, topical or rectal administration comprise one or more compounds of Formula I with a suitable vehicle. The active ingredients are stated to possess estrogenic, uterotrophic, hypocholesterolemiant and antizygotic activity.