Process for the production of reduction products of the male sexual hormone and like substances

摘要

The male sexual hormone together with compounds of saturated and unsaturated cyclopentanophenanthrols which contain a keto group insofar as they exhibit the action of the male sexual hormone and contain no benzene ring in the molecule are reduced to saturated alcohols. The reduction is preferably carried out in alcoholic solution by the action of sodium, or by the action of aluminium foil in the presence of water, or by catalytically activated hydrogen under elevated pressure. In all cases care must be taken that the reduction does not proceed beyond the alcohol stage to the desoxo product. The reduction products possess a physiological activity many times that of the starting materials, which may be the male sexual hormone C19H30O2, or its unsaturated derivatives of formula C19H28O2 or the materials of the formula C18H28O2 obtained according to Specification 421,681. Crude extracts of products with the activity of the male sexual hormone as are obtained from urine, body liquids, organs, and the like can also be converted by reduction into diols of essentially higher value. In examples: (1) crystalline male sexual hormone of the formula C19H30O2 is reduced by sodium in alcoholic solution to give a product of formula C19H32O2; (2) crystalline male sexual hormone is treated in cyclohexanol solution with hydrogen under pressure in the presence of a nickel catalyst. The reduction product exhibits a physiological activity of 5 times that of the parent material. Specification 346,130 also is referred to.