DE1693240

• Main Authors: HALPERN, OTTO, BOWERS, ALBERT
• Format: Patent
• Language: English
• Published: 03.01.1974
• Edition: 1
• Subjects: CHEMISTRY; METALLURGY; ORGANIC CHEMISTRY; STEROIDS

3 - Desoxy - D 1,3,5(10)-steroids are prepared by treating a 3-hydroxy-D 1(10),5-19-nor-steroid of the androstane, pregnane or sapogenin series with a mineral acid, a strong organic acid, phosphorus oxychloride, phosphorus pentachloride or thionyl chloride in an inert organic solvent at between 0 DEG C. and reflux temperature for a period of time of between 10 minutes and 24 hours The products of the formula <FORM:1065386/C2/1> (wherein A is keto or the group a -R1,b -OR in which R is hydrogen or a hydrocarbon carboxylic acyl radical of less than 12 carbon atoms which is optionally substituted and R1 is hydrogen, C1- 8 alkyl, C2- 8 alkynyl or C2- 8 alkenyl; and X is C1- 6 alkyl, C2- 6 alkenyl or C2- 6 alkynyl) are novel. They are admixed with the 6b -isomers when prepared as described above, and are separated from them by standard procedures. 17-Keto products may be converted to 17a -R1,17b -OR products by standard procedures. Other starting materials may have at position 17 a b -acetyl group with or without 17a -acyloxy, the 17,20: 20,21-bismethylenedioxy group or a sapogenin side-chain. They may also contain, for example, a D 16 double bond, a 16a ,17a -acetonide group, an 11-keto group or a 16a - or 16b -methyl group. The steroids of the invention, which are stated to have an anti-androgenic action, may be made up into pharmaceutical compositions with suitable carriers.