GB863779A - Improvements in or relating to steroids and the manufacture thereof - Google Patents

Abstract

The invention comprises steroid compounds having the general formula: <FORM:0863779/IV (b)/1> wherein R is alkyl or aryl radical, R1 is a hydroxy or keto group, R11 is iodine, fluorine or the group -O-SO2-R111 wherein R111 is a lower alkyl radical, phenyl, tolyl or naphthyl, and a process for the preparation thereof wherein a compound having the general formula: <FORM:0863779/IV (b)/2> is treated with an organic sulphonyl halide to obtain a compound having the general formula: <FORM:0863779/IV (b)/3> and then if desired treating the latter compound with an alkali metal iodide to produce the corresponding 21-iodo derivative, if desired treating the latter compound with silver fluoride to produce a compound having the general formula: <FORM:0863779/IV (b)/4> and then if desired oxidising the 11-hydroxy substituent when present to the corresponding 11-keto derivative. As oxidising agent there may be used chromic anhydride. Specific compounds claimed are 6a -methyl-11b , 17a -dihydroxy- 21- fluoro- 4- pregnene- 3, 20- dione, 6a -methyl-17a -hydroxy- 21-fluoro-4-pregnene-3, 11, 20- trione, 6a - methyl- 11b , 17a -dihydroxy-21-iodo-4-pregnene-3, 20-dione, and a 21- sulphonate of 6a - methyl- 11b , 17a , 21-trihydroxy- 4- pregnene- 3, 20- dione. Specifications 826,627 and 863,782 are referred to.ALSO:6 - Methyl - 11b ,17a - dihydroxy - 21 - fluoro - 4 - pregnene - 3,20 - diones and 6 - methyl - 17a - hydroxy - 21 - fluoro - 4 - pregnene - 3,11,20 - triones are useful in oral, parenteral and topical compositions, e.g. as ointments, lotions, jellies, creams, suppositories, bougies, aqueous suspensions &c. Alternatively other 6a -alkyl or 6a -phenyl compounds or the 6b -alkyl or 6b -phenyl compounds may be employed. A dermatological and ophthalmic ointment incorporates 6a - methyl - 11b ,17a - dihydroxy - 21 - fluoro-4-pregnene-3,20-dione. In addition there may be present neomycin sulphate, bacitracin, circulin, polymyxin B sulphate, gramicidin, streptomycin sulphate, dihydrostreptomycin sulphate, oxytetracycline, chlorotetracycline, tetracycline, chloramphenicol and sulphonamides. Specifications 826,629 and 863,782 are referred to.