NOVEL 19-NOR-PREGNAHEXAENES, PROCESS FOR THE PREPARATION THEREOF, AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM

摘要

19-Nor-pregnahexaenes of formula wherein A is hydrogen, lower alkyl, fluoro or fluoro-substituted methyl; R1 is hydrogen, lower alkyl, or an acyl radical of a carboxylic acid; W is (H, H); (H, lower alkyl); (H, alpha -OR2), with R2 being hydrogen or an acyl radical of a carboxylic acid; or = CHT, with T being hydrogen, lower alkyl, fluorine, or chlorin; Q is OR4, with R4 being hydrogen or an acyl radical of a carboxylic acid; hydrogen, provided W is (H, H) or (H, lower alkyl); or together with W represents a 16 alpha , 17 alpha -lower alkylidenedioxy grouping; Y is (H, H), (H, OH), or oxygen; Z is hydrogen, chlorine or bromine; R3 is hydrogen or an acyl radical of a carboxylic acid; or OR3 together with Q represents an alkylidenedioxy or alkylorthoalkanoate grouping; and when Q is hydroxy and R3 is hydrogen, the 17 alpha , 20; 20, 21-bismethylenedioxy derivatives thereof; These compounds are novel, with the exception of the 21-acetate and 3,21-diacetate of 19-nor-pregna- 1,3,5 (10), 6,8,14- hexanene-3,17 alpha , 21- triol-20-one, while pharmaceutical compositions containing the latter two compounds are also novel. The preparation of the novel compounds by three methods is described, in particular dehydrogenation in position 14 of appropriate 19-nor-pregna- 1,3,5(10), 6,8-pentaenes by DDq. Representative compounds of the inventions have been shown to exhibit antimitotic activity and, in particular, are useful in treating psoriasis.