GB943951A - New steroid compounds, and processes for their preparation - Google Patents

Abstract

The invention comprises 17b -hydroxy-18-nor-pregn-4-ene-3, 11, 20-trione derivatives and its 21-esters having the formula: <FORM:0943951/C2/1> where R is hydrogen or an acyl radical derived from an organic carboxylic acid having 1-7 carbon atoms and processes for the preparation thereof either by subjecting 17b -hydroxy-18-nor-pregn-4-en-3, 11, 20-trione to the action of the diastases secreted by an active culture of Colletotrichum lindemuthianum so as to introduce a hydroxyl group at the 21-position which may be optionally esterified, or by subjecting 17b -hydroxy-18-nor-pregn-4-ene-3, 11, 20-trione to halogenation, followed by acyloxylation of the resultant 17b -hydroxy-21-halogeno-18-nor-pregn-4-ene-3, 11, 20-trione which may be optionally saponified. Halogenation may be effected with iodine in the presence of calcium oxide and acyloxylation with an alkali metal acetate in the presence of acetic acid. The starting 17b -hydroxy-18-nor-pregna-3 11, 20-trione may be obtained by ketalising 18-nor-pregn-16-ene-3, 11, 20-trione at 3-position, subjecting the product to epoxidation to form the corresponding 16, 17-ozonide, treating the product with hydrobromic acid to obtain a 16-bromo-17-hydroxy compound, subjecting the product to catalytic reduction to form 17b -hydroxy-18-nor-pregna-3, 11, 20-trione which is then dehydrogenated to obtain the desired 17b -hydroxy-18-nor-pregn-4-ene-3, 11, 20-trione. Dehydrogenation may be effected by bromination to form a 4-bromo compound followed by dehydrobromination. Specifications 943,953, 943,954 and 943,955 are referred to.