ALKYL AND HALOALKYL ANDROST-4-ENE AND ANDROSTA-1,4-DIENE17-CARBOXYLATES

摘要

Steroids with antiinflammatory activity and the formula I in which R' is methyl, ethyl, n-propyl or isopropyl; R'' is methyl, chloromethyl, fluoromethyl, bromomethyl, iodomethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl or 2-iodoethyl; X is hydrogen or fluorine; and @ is a single or double bond are prepared by esterifying or transesterifying, respectively, with an agent supplying the radical R'' or the radical R', respectively, a corresponding 17 alpha -acyloxy-17ss-carboxylic acid or a functional derivative thereof or a 17 alpha -hydroxy-17ss-carboxylate. Resulting DELTA 1-steroids of the formula I can subsequently be reduced to the corresponding saturated compounds or resulting 1,2-saturated compounds can be dehydrogenated to the corresponding DELTA 1 compounds. In addition, halogen substituents present in the group R'' can be replaced by other halogens; thus, for example, compounds of the formula I in which R'' is an alkyl group substituted by chlorine, bromine or iodine can be converted by this exchange reaction to the corresponding fluoroalkyl compounds. The compounds of the formula I are distinguished by very good antiinflammatory activity and can be converted into pharmaceuticals for topical or internal administration. IMAGE