GB843214A — Improvements in or relating to steroid compounds

USPTO Abstract

The invention comprises steroid compounds of the general formula: <FORM:0843214/IV(b)/1> wherein X represents <FORM:0843214/IV(b)/2> or = O and R and R1 represent hydrogen, the formyl radical or an alkanoyl radical containing not more than 8 carbon atoms, and the preparation thereof by heating a compound of the general formula: <FORM:0843214/IV(b)/3> wherein X represents <FORM:0843214/IV(b)/4> or = O and R and R1 represent the formyl radical or an alkanoyl radical containing not more than 8 carbon atoms with an alkali metal salt of an alkanoic acid containing not more than 8 carbon atoms such as sodium or potassium acetate, or an alkali metal formate, and, when R and R1 represent hydrogen in the above general formula of the 2-substituted-steroids, hydrolysing the resulting ester compound. The preferred reactants for the above process are 6-bromo-4-pregnane-17 a ,21-diol-3,11,20-trione 21-acetate and 6-bromo-4-pregnene-11b ,17 a ,21-triol-3,20-dione 11-formate 21-acetate which may be converted into 4 - pregnene - 2, 17 a , 21-triol-3,11,20-trione and 4-pregnene-2,11b 17 a , 21 - tetrol - 3, 20 - dione respectively as well as the corresponding 2,21-diesters defined above such as the 2,12-diacetates. In the examples, 4-pregnene-2, 17 a , 21-triol-3,11,20-trione and the 2, 21 - diacetate thereof, and 4-pregnane-2, 11b , 17 a ,21-tetrol-3,20- dione and the 11 - formate 2, 21-diacetate thereof are prepared. 6 - Bromo - 4 - pregnene - b 11,17 a ,21 - triol-3, 20 - dione 11-formate 21-acetate is prepared by brominating 4-pregnene-11b ,17 a ,21-triol 11-formate 21-acetate with N-bromo-succinimide. 1,4-Pregnadienes are prepared by treating the 2-substituted steroids of the above general formula with a dehydrating agent such as hydrogen bromide in acetic acid, e.g. the 21-acetate of dehydrocortisone may be prepared from the corresponding 2,21-diacetate-4-pregnene.