Contragestational agents. 1. Steroidal-O-aryloximes

Authors:
  • AHAllen F. Hirsch
    Allen F. Hirsch
  • GAGeorge O. Allen
    George O. Allen
  • BWBenny Wong
    Benny Wong
  • SRSandra Reynolds
    Sandra Reynolds
  • CEChris Exarhos
    Chris Exarhos
  • WBWilliam Brown
    William Brown
  • DHDo Won Hahn
    Do Won Hahn
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Abstract
The preparation of a series of O-aryloximes of various steroids by 2 different routes is described. These compounds were prepared by reacting a keto steroid with a substituted O-arylhydroxylamine in the presence of an acid catalyst or, alternatively, by the reaction of a steroidal oxime with a substituted aryl halide in the presence of a suitable base. These compounds were examined for their ability to interrupt postimplantive gestation in female rats. The most significant contragestational activity was seen with compounds in which the basic steroid structure was a 5.alpha.-androstane and the 3-oxime was of the p-nitrophenyl series. One of the most active compounds in the series has the ability to terminate pregnancy when orally administered to rats at 2.5 mg/kg on days 9-12 of gestation. This compound apparently was devoid of androgenic activity at this dose level.

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