GB829903A - Steroids and the preparation thereof - Google Patents

Abstract

The invention comprises 1,4-androstadiene3,17-dione in which the substituent on the 11carbon is a -hydroxy, b -hydroxy, or keto, 5a androst - 1 - ene - 3,11,17 - trione, 1 - dehydrotestosterone in which the substituent on the 11-carbon is a -hydroxy, b -hydroxy or keto, 1 - dehydro - 11a - hydroxy - 17a - methyl - testosterone, 1 - methoxy - 11b ,21 - dihydroxy - 4,17(20) - pregnadiene - 3 - one, and a process which comprises growing a fungus of the genus Septomyxa under aerobic conditions in the presence of a nutrient medium and a steroid compound containing a 1,2-saturated linkage to cause dehydrogenation at the 1,2-position or degradation of the 17-side chain if present to 17-hydroxy or 17-keto, or both dehydrogenation at the 1,2-position and degradation of the side chain. Particularly valuable products which may be prepared are represented by the general formula <FORM:0829903/IV (b)/1> wherein X is methylene, hydroxymethylene or carbonyl, Y is hydrogen or halogen, Z is hydroxy, acyloxy or keto, R is hydroxyacetyl or acetyl, R1 is hydrogen or hydroxy or R and R1 taken together are <FORM:0829903/IV (b)/2> or carbonyl and R2 is hydrogen or methyl. Species of the genus Septomyxa which are useful are Septomyxa affinis, Septomyxa sesculi, Septomyxa corni, Septomyxa salicina and Septomyxa tulasnei. The fungus is grown under submerged aerobic conditions in a nutrient medium which comprises assimilable non-steroidal carbon, e.g. a carbohydrate, a source of nitrogen, e.g. vegetable or animal proteins and mineral constituents, e.g. sodium or ammonium phosphate. As starting steroids there may be employed progesterone, 11b ,17a ,21 - trihydroxy - 4 - pregnene-3,20-dione, 11b ,21-dihydroxy- D 14,7(20)-pregnadiene-3-one or a 21-acylate thereof, 17a -methyltestosterone and 11a -hydroxyallopregnane-3,20-dione. Many other starting steroids are listed. Examples describe the preparation of 1,4 - androstadiene - 3,17 - dione, 1 - dehydrotestosterone, 1 - dehydrotestololactone, 17a ,21-dihydroxy - 1,4 - pregnadiene - 3,20 - dione, 1-dehydro-17a -hydroxyprogesterone, 1-dehydro-11 - desoxycorticosterone, 1 - dehydroproges - terone, 1 - dehydro - 19 - normethyltestosterone, 11b ,21 - dihydroxy - 1,4,17(20) - pregnatriene-3-one, 17a ,21 - dihydroxy - 1,4 - pregnadiene - 3,11,20-trione, 11b ,17a ,21 - trihydroxy - 1,4 - pregnadiene-3,20-dione, 1 - dehydro - 11 - keto - progesterone, 1 - dehydro - 11a - hydroxyprogesterone and 1 - dehydro - 11a - hydroxy - 17a -methyltestosterone. Specification 724,094 is referred to. Reference has been directed by the Comptroller to Specification 807,227.