GB853981A - Improvements in or relating to steroids and the manufacture thereof - Google Patents

Abstract

The invention comprises a compound of the formula: <FORM:0853981/IV(b)/1> wherein R is an 11b -hydroxy or an 11-keto group, R1 is hydrogen or acyl, in which the acyl group is of a hydrocarbon carboxylic acid containing from 1-12 carbon atoms inclusive and R111 is an alkyl or aryl radical provided that when the substituent represented by R111 is in the b -position R1 represents hydrogen, a process for the production of a 1-dehydro-6-alkyl or aryl cortisone, a 1-dehydro-6-alkyl or aryl hydrocortisone and 21-acyl esters of 6a -substituted compounds which comprises growing a microorganism from the group consisting of the genera Corynebacterium, Didymella, Calonectria, Alternaria, Collectotrichum, Cylindrocarpon, Ophiobolus, Septomyxa, Fusarium, Listeria and Erysipelothrix in a nutrient medium containing assimilable non-steroidal carbon, nitrogen and phosphorus, and a 4-pregnene of the formula: <FORM:0853981/IV(b)/2> and a process for the production of a compound having the formula: <FORM:0853981/IV(b)/3> wherein R is an 11b -hydroxy or an 11-keto group, R1 is hydrogen or acyl, in which the acyl group is of an organic carboxylic acid containing 1-12-carbon atoms inclusive, which comprises subjecting the corresponding 1,2-saturated compound to chemical dehydrogenation e.g. with SeO2. Illustrative products of the invention are 1-dehydro-6a -methyl hydrocortisone, 1-dehydro-6 a -methylcortisone, 1-dehydro-6 b -methyl-hydro-cortisone, 1-dehydro-6a -methylhydrocortisone 21-acetate, 1-dehydro-6 b -methyl cortisone, 1-dehydro-6a -methylcortisone 21-acetate and 1-dehydro-6a -methylhydrocortisone 21-hemisuccinate. Specifications 724,094 and 826,629 are referred to.ALSO:Compounds of the formula: <FORM:0853981/VI/1> wherein R is an 11 b -hydroxy or an 11-keto group, R1 is hydrogen or acyl, in which the acyl group is of a hydrocarbon carboxylic acid containing 1-12 carbon atoms inclusive and R111 is an alkyl or aryl radical provided that when the substituent represented by R111 is in the b -position R1 represents hydrogen are incorporated in tablets, capsules, liquid suspensions or solutions for oral use, in ointments, bougies lotions and jellies for topical use, in aerosols for nasal use, in a sterile diluent for parenteral use and in eye or ear drops. Tablets for oral use comprise 1-dehydro-6-methylhyrodcortisone and may incorporate in addition antibioctics, e.g. tetracycline, chlortetracycline, chloramphenicol, penicillin, novobiocin or oxytetracycline, and sulpha drugs, aspirin and /or vitamins. An ointment comprises 1-dehydro-6a -methylhydrocortisone and neomycin sulphate. Other antibiotics mentioned are polymyxin, B sulphate, bacitracin, gramicidin and tyrothricin. Specifications 724,094 and 826,629 are referred to.