GB779002A - Steroid compounds - Google Patents

Abstract

The invention comprises a 3-amino-11,21-dihydroxy-3,5,17(20)-pregnatriene represented by the formula <FORM:0779002/IV(b)/1> wherein R3 is an alkylene group containing less than nine carbon atoms which, together with the nitrogen atom, forms a ring which contains five or six members and a process which comprises reducing a 3-amino-11-oxygenated-3,5, 17(20) - pregnatriene - 21 - oic acid alkyl ester wherein the amino group is represented by the formula R3N-with lithium aluminium hydride in an organic solvent, decomposing any excess lithium aluminium hydride and organo-metal complexes, and hydrolysing the thus-produced 3 - amino - 11,21 - dihydroxy - 3,5,17(20) - pregnatriene with aqueous solution to produce an 11,21 - dihydroxy - 4,17(20) - pregnadiene-3-one. The hydrolysis of the 3-amino group to a 3-keto group may be effected in neutral, acidic or alkaline aqueous solution. The 17-hydroxy group may be introduced into the final product by treating the 11,21-dihydroxy-4,17(20)-pregnadiene-3-one with osmium tetroxide to form a 17,20-osmate ester which is subsequently treated with for example chloric acid, perchloric acid, hydrogen peroxide, perbenzoic or peracetic acid. As starting materials there may be used the methyl and ethyl esters of 3-pyrrolidyl-11-keto-, 11a -hydroxy- or 11b -hydroxy-3,5,17(20)-pregnatriene-21-oic acid. Examples describe the preparation of 3 - pyrrolidyl - 11b ,21 - di - hydroxy - 3,5,17(20 - pregnatriene and compounds in which the 3-amino group is piperidyl, pyrrolidyl and C-alkyl substituted derivatives thereof, i.e. 21-methyl-piperidyl, 31-ethyl-piperidyl 21 - methyl - pyrrolidyl and 31 - isopropyl - pyrrolidyl, and of 11b ,21-dihydroxy-4,17(20)-pregnadiene-3-one, and 11b ,17a ,21-trihydroxy-4-pregnene-3,20-dione.