1,198,003. Steroid-14α,15α-diols and ketals thereof. UPJOHN CO. 7 March, 1968 [3 April, 1967], No. 11197/68. Heading C2U. Novel steroids of the formulµ (wherein there are optional #SP1/SP and #SP6/SP double bonds in the 14α,15α-substituted methylenedioxy compounds; Z is CH 2 or CO ahd ZSP1/SP has these values or can additionally be CH(#-OH); R and RSP1/SP are each H or C 1-12 alkyl; and a and b are each C 1-12 alkyl, phenyl or benzyl) are prepared by the processes (I) # (II) is effected microbiologically e.g with Penicillium urticae ATCC 10120; (II) # (III) is esterification with an alkyl haloformate; (III)# (IV) is pyrolysis; (IV)# (V) is a Favorskii rearrangement; (V) # (VI) is oxidation with, for example, OsO 4 , or KMnO 4 in weak acid solution; (VI)# (VII) is ketalization; (VII) # (VIISP1/SP) is reduction to the 3#,11#-diol and (VIISP1/SP) # (VIII) is reoxidation to the 3-one, and (VII) # (IX) and (VIII) # (X) are dehydrogenations to the #SP1,6/SP-#SP4,6/SP-and #SP1,4,6/SP-compounds. Hydrolysis of any of the 21-oic acid esters gives the free acids. Pharmaceutical compositions comprise any of the novel steroids, which have anti-inflammatory, anri-viral, anti-microbial and antihormonal activities, and suitable carriers.
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