GB805830A - Steroid compounds - Google Patents

Abstract

The invention comprises 21-sulphonated cyclopentanophenanthrene compounds of the general formul <FORM:0805830/IV (b)/1> and <FORM:0805830/IV (b)/2> wherein R represents a keto or b -hydroxy group and R11 represents an alkyl group, and the preparation thereof by reacting the required 21-hydroxy compound with an alkyl sulphonyl chloride, and in the case of compounds of the general formula A by treating compounds of the general formula B with ethylene glycol or with an ethylenedioxy-yielding compound in an exchange reaction, e.g. in the presence of a strong acid, such as p-toluene sulphonic or sulphuric acid. The R11 group may be a C1 to C6 alkyl group-preferably the methyl group. The sulphonation may be carried out in solution in benzene, toluene, tetrahydrofuran, dioxane or a tertiary amine. The reaction may be carried out at a temperature of about 0 DEG C. for from 1 to 3 hours. The above process may be modified in that the required 21-hydroxy compound is prepared by hydrolysing the corresponding 21-acyloxy compound. This process may be further modified in that in the case of 21-acyloxy compounds containing the 3-ethylenedioxy-5-pregnene structure, the 21-acyloxy compound is prepared by the process claimed in Specification 785,686. Suitable ethylenedioxy yielding compounds are ethylenedioxy derivatives of lower aliphatic ketones such as acetone, methyl ethyl ketone or mesityl oxide. The reaction to form the 3-ethylenedioxy derivatives may be effected in an inert solvent such as benzene, toluene, xylene, tetrahydrofuran or dioxane. In the examples 3,11,20-triketo-17a ,21 - dihydroxy - D 4 - pregnene - 21 - methanesulphonate is prepared by treating cortisone with methanesulphonyl chloride, and 3-ethylenedioxy - 11,20 - diketo - 17a ,21 - dihydroxy - 5-pregnene-21-methanesulphonate is prepared by treating 3,11,20-triketo-17a ,21-dihydroxy-4 - pregnene - 21 - methanesulphonate with mesityl oxide, and by hydrolysing 3-ethylene-dioxy - 11,20 - diketo - 17a ,21 - dihydroxy - D 4 - pregnene 21-acetate to the corresponding 21-ol and then reacting the 21-ol with methanesulphonyl chloride.