IE33946L - 3-desoxo-19-nor-steroids - Google Patents

Abstract

1292201 3 - Unsubstituted - 7 - alkyl - androstane compounds ORGANON LABORATORIES Ltd 21 Jan 1970 [30 Jan 1969] 2895/70 Heading C2U Novel steroids of the formula wherein R 1 is C 2-4 alkyl; R 2 is an oxo group or (α-X) (#-Y) in which X is H or C 1-6 alkyl, alkenyl, alkadienyl, alkynyl or alkadiynyl and Y is free, esterified or etherified OH; R 3 is C 1-4 alkyl; and there is present a #<SP>4</SP>-, #<SP>5(10)</SP>- or #<SP>5</SP>-double bond, are prepared from the corresponding steroids containing in position-3 a cyclic or non-cyclic dithioketal group or a halogen atom or an aliphatic-, aromatic- or araliphatic-sulphonyloxy group, by reductive splitting off of the 3-substituent. Preferably, for preparation of #<SP>4</SP>- or #<SP>5(10)</SP>-compounds the 3- thioketals are treated with an alkali metal in liquid ammonia or a C 1-4 aliphatic primary amine, while for preparation of the #<SP>5</SP>-compounds the 3-halo or -sulphonyloxy steroids are treated in the same manner or with an alkali metal in an alcohol or with an alkali metal aluminium hydride. In the products the 17- substituents may be interconverted by standard procedures. Starting materials of the formula wherein R 4 is a cyclic or non-cyclic dithioketal group or (H) (Z) in which Z is a halogen atom or a sulphonyloxy group are prepared by thioketalization of the corresponding 3-keto steroids or esterification of the corresponding 3-ols. #<SP>5</SP> - 3#,17# - Dihydroxy - 7α,18 - dimethylestrene 17-benzoate is prepared by NaBH 4 reduction of #<SP>3</SP>'<SP>5</SP> - 3# - acetoxy - 17# - benzoyloxy- 7α,18 - dimethyl - estradiene, itself prepared by enol acetylation of the corresponding #<SP>4</SP>-3-one. The steroids of the invention are stated to possess progestative, anabolic, androgenic, estrogenio, ovulation-inhibiting and anti-fertilization properties. They may be made up into pharmaceutical compositions with suitable carriers. [GB1292201A]