ES284727A1 - Procedure for preparing new steroids of the androstanic series (Machine-translation by Google Translate, not legally binding) - Google Patents

Abstract

Procedure to prepare new steroids of the androstanic series, of formula I ** (See formula) ** where R1 means methyl, ethyl or propyl, R2 means methyl or ethyl, and R3 means hydrogen or a radical of C6-C6carboxylic acid at most, as well as its 1-dehydro derivatives, characterized in that: a) a 5-dehydro-7-alkoxy-17alpha-alkyl steroid of the formula II ** (See formula) ** where R1, R2 and R3 have the meaning already stated and R4 means hydrogen or acyl, optionally after pre-saponification of the 3-acyl group, it is treated with a mildly oxidizing chemical agent or with microorganisms which, as is known, can oxidize an existing hydroxy group on a steroid as well as optionally saponify an ester group, as preferred Flavobacterium de hydrogenans, or under mild conditions, with microorganisms that are usually used to introduce a double bond 1.2 on steroids, O well b) a 3-keto-7-alkoxy-17alpha-alkyl steroid of the formula III ** (See formula) ** where R1, R2 and R3 have the meaning already stated, which has a halogen atom in position 4 or 5, is treated with a dehydrohalogenating agent, O well c) in a 3-keto-7-alkoxy-5-dehydro-17alpha-alkyl steroid of the formula IV ** (See formula) ** where R1, R2 and R3 have the meaning already stated, the double bond 5,6 is moved to position 4,5 by known isomerization processes, preferably by treatment with an alkaline or acidic agent or with iodine, the 3-keto group also being able to be functionally modified if acidic isomerization agents are used, O well d) the 7-alkoxysteroids of the formula I saturated in position 1,2 are dehydrogenated in position 1,2, by treatment with chemical or microbiological agents of dehydrogenation, or treated with microorganisms that dehydrogenate in position 1,2 a steroid of Formula II, optionally after previous saponification of an acylated hydroxy group which is in position 3, O well e) a steroid of the formula V is dehydrohalogenated ** (See formula) ** where R1, R2 and R3 have the meaning already stated and X means chlorine, bromine or iodine, in a manner known per se, by treatment with acid-binding agents, and likewise f) a free hydroxy group existing in the 17-position in the final products obtained is esterified by processes already known per se, or a functionally modified hydroxy group is liberated by processes already known per se. position. (Machine-translation by Google Translate, not legally binding)