1429951 Steriod nitroaryl oximes ORTHO PHARMACEUTICAL CORP 1 June 1973 [2 June 1972] 26348/73 Addition to 1299650 Heading C2U The invention comprises compounds of formula wherein either (A) R is H, R 1 is Cl or Br, R 2 is OH or OCOMe, R 3 is H, or R 2 and R 3 together are oxo (provided that when R 1 is Br then R 2 is other than OCOMe); or (B) R is H or NO 2 , R 1 is 2-hydroxy-5-nitrophenyl, R 2 is OCOMe and R 3 is H. Compounds I are prepared either from the corresponding 3-ones by acid-catalysed reaction with an appropriate O-aryl-hydroxylamine, or from the corresponding 3-hydroxyimino compounds by base-catalysed reaction with an appropriate aryl halide. A 17#-ol product may oxidized to a 17-one. 2 - (2 - Hydroxy - 5 - nitrophenyl) - 17#- acetoxy - 5 - androstan - 3 - one is prepared from 17# - acetoxy - 3 - (p - nitrophenoxyimino)- 5-androstane by overnight stirring with HCl/ AcOH. 2 - Chloro - 17# - hydroxy - 5 - androstan - 3- one is prepared as described in Specification 1,429,952. Compounds I are said to possess antilittering and antiandrogenic properties, and may be made up with carriers into pharmaceutical and veterinary compositions for oral administration.
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