procedure for the construction of hydroxyacetylseitenkette of steroids of the pregnan type, 21 - hydroxy - 20 - oxo 17alpha - pregnan compounds and pharmaceutical praeparate containing the same.

摘要

The present invention relates to a novel general process for synthesizing a alpha - or beta -oriented hydroxyacetyl side chain of steroids of the pregnane type, which comprises treating a corresponding steroid carbaldehyde in succession with formaldehyde dimethylmercaptal-S-oxide in the form of an alkali metal salt thereof, and with a strongly acid hydrolysing agent. Preferred final products are compounds of the formula IMAGE (IA) wherein n is 1 or 2, R2 represents methyl or difluoromethyl, and R1 represents hydroxymethyl, methoxymethyl, acetoxymethyl or hydrogen, and, if n is 2 and/or R2 is difluoromethyl, R1 also represents methyl. These compounds act as agonists or antagonists of natural steroid hormones. The antigestagenic 19,21-dihydroxy-17 alpha -pregn-4-ene-3,20-dione and its 6,7-dehydro derivatives and diacetates are of particular interest.