Ciba-geigy Corporation

Julius Schmidlin

Michel Biollaz

Novel 17.beta.-methoxycarbonyl derivatives of the androstane series of the formula ##STR1## in which R represents alkyl having from 1 to 4 carbon atoms are distinguished by a high local anti-inflammatory activity without having any systemic side effects. The compounds are manufactured by conventional processes of steroid chemistry.

Novel carboxylic acid esters

The present invention provides a novel process for the manufacture of 17- and 17a-carboxylic acids of the androstane and D-homo-androstane series respectively, of the following partial formula of the ring D ##STR1## wherein R represents a hydrogen atom or an unsubstituted or substituted hydrocarbon radical or a free or functionally modified hydroxyl group, and wherein the carboxyl group can be in the .alpha.- or .beta.-position, and of the salts and functional acid derivatives thereof, in particular their esters. The new process consists in the oxidative degradation of the side chain of corrsponding 20, 21-ketoaldehydes of the pregnane or D-homopregnane series or of the 17.alpha.-pregnane or 17a.alpha.-D-homopregnane series with an organic peracid in an inert solvent, preferably at temperatures between -20 and +30.degree. C, and optionally converting free functional groups present into their derivatives or setting free functional groups from substituents which are derivatives of such groups.

Process for the manufacture of steroid carboxylic acids and the esters

A new method for converting 11.beta.,18; 18,20-bis-epoxy-pregn-20-enes to 11.beta.,18-epoxy-18,21-dihydroxy-20-oxo-pregnane compounds or functional derivatives thereof is described and claimed. It consists in treating said bis-epoxy compounds with a heavy metal acylate having an acyloxylating action, such as lead - (IV), cerium - (IV), mercury - (II) and thallium - (III) - acylates. Preferred agent is lead tetraacetate. The reaction is conducted in a solvent or suspending agent like benzene or its homologs or chlorinated paraffins, like methylene chloride, preferably at room temperature and optionally in the presence of an acid. In the 21- acylates of 11.beta.,18-epoxy-18,21-dihydroxy-20-oxo-pregnane compounds thus obtained the 21-hydroxy group and any other protected functional groups can be set free in manner known. The process is especially important for the manufacture of aldosterone or its derivatives.

Growing community of inventors

Basel, Switzerland

Julius Schmidlin