GB824351A - New steroids of the í¸-pregnadiene series and the preparation of í¸-pregnadienes - Google Patents

Abstract

The invention comprises D 1,4-pregnadienes of the general formula <FORM:0824351/IV (b)/1> wherein X represents hydrogen or a halogen atom, Y represents a methylene, hydroxymethylene or carbonyl group, Z is a hydroxymethylene group or an alkanoyloxymethylene group in which the alkanoyl portion contains up to 6 carbon atoms, R1 represents hydrogen or a hydroxy group, and R represents hydrogen or an alkanoyl group containing up to 6 carbon atoms, and a process for the preparation thereof by subjecting the corresponding D 4-pregnene to the fermentative enzymatic action of microorganisms of the fungi of the genus Nocardia or of Corynebacterium simplex. The fungus of the Nocardia genus may be N. corallina, N. asteroides, N. keratolyticus, N. transvalensis, N. erythropolis, N. convoluta, N. gardneri, N. leishmanii, N. opaca, N. blackwelii, N. caviae, N. cuniculi, N. globerula, N. polychromogenes, N. farcinica, and N. sylvodifera. A nutrient medium containing the said D 4-pregnene reactant may be inoculated with the fungus and fermentation effected under submerged aerobic conditions. The medium preferably contains assimible carbon, nitrogen and mineral salts. Suitable D 4-pregnenes which may be used in the above process are D 4-pregnene-11b ,16a ,17a ,21-tetrol - 3,20 - dione, D 4 - pregnene - 9a - fluoro - 11b ,16a ,17a ,21 - tetrol - 3,20 - dione and D 4 - pregnene - 16a ,17a ,21 - triol - 3,11,20 - trione, and esters thereof. In the examples, the following compounds are prepared: D 1,4-pregnadiene - 17a ,21 - diol - 3,20 - dione, D 1,4 - pregnadiene - 11b ,21 - diol - 3,20 - dione, D 1,4 - pregnadiene - 11(a and b ),17a ,21 - triol - 3,20 - dione, D 1,4 - pregnadiene - 11b ,16a ,17a ,21 - tetrol - 3,20-dione and the corresponding 16,21-diacetate, and D 1,4 - pregnadiene - 9a - fluoro - 11b ,16a ,17a - tetrol - 3,20 - dione and the corresponding 16,21-diacetate. The bis-2,4-dinitrophenylhydrazone of D 1,4-pregnadiene-9a -fluoro - 11b ,16a ,17a ,21 - tetrol - 3,20 - dione, 16,21-diacetate is also prepared.ALSO:A therapeutic composition in the form of a tablet, powder, pill, solution or suspension contains as the active ingredient a 1,4-pregnadiene of the general formula <FORM:0824351/VI/1> wherein X represents hydrogen or a halogen atom, Y represents a methylene, hydroxymethylene or carbonyl group, Z represents a hydroxymethylene group or an alkanoyloxymethylene group in which the alkanoyl portion contains up to 6 carbon atoms, R1 represents hydrogen or an hydroxy group, and R represents hydrogen or an alkanoyl group containing up to 6 carbon atoms.