GB863780A - Improvements in or relating to steroids and the manufacture thereof - Google Patents

Abstract

The invention comprises steroid compounds having the general formula: <FORM:0863780/IV (b)/1> wherein R is an 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 napthyl, and a process for the preparation thereof wherein a compound having the general formula: <FORM:0863780/IV (b)/2> is treated with an organic sulphonyl halide to obtain a compound having the general formula: <FORM:0863780/IV (b)/3> and then if desired the latter compound is treated with an alkali metal iodide to produce the corresponding 21-iodo derivative, and if desired the latter compound is treated with silver fluoride to produce a compound having the general formula: <FORM:0863780/IV (b)/4> which may be oxidised to the corresponding 11-keto derivative. As organic sulphonyl halide there may be used an acid halide of methanesulphonic acid, ethanesulphonic acid, propanesulphonic acid, benzenesulphonic acid, p-toluenesulphonic acid or a - or b -naphthane sulphonic acid. As alkali metal iodide, sodium or potassium iodide may be employed. Oxidation may be effected with chromic acid. Specific compounds claimed are 6a -methyl-11b , 17a -dihydroxy-21-fluoro-1, 4-pregnadiene-3, 20-dione, 6a -methyl-17a -hydroxy-21-fluoro-1, 4-pregnadiene-3, 11, 20-trione, 6a -methyl-11b , 17a -dihydroxy-21-iodo-1, 4-pregnadiene-3, 20-dione and 21-sulphonates of 6a -methyl-11b , 17a , 21-trihydroxy-1, 4-pregnadiene-3, 20-dione. Specifications 853,981 and 863,781 are referred to.ALSO:6 - Methyl - 11b ,17a - dihydroxy - 21 - fluoro - 1,4 - pregnadiene - 3,20 - diones and 6 - methyl - 17a - hydroxy - 21 - fluoro - 1,4 - pregnadiene - 3,11,20 - triones are employed in oral, parenteral and topical compositions, e.g. tablets, ointments, lotions, jellies, creams, suppositories, bougies and aqueous suspensions. A dermatological and ophthalmic ointment comprises 6a - methyl - 11b ,17a - dihydroxy - 21 - fluoro - 1,4 - pregnadiene - 3,20 - dione. An antibiotic such as neomycin sulphate, bacitracin, circulin, polymyxin B sulphate, gramicidin, streptomycin sulphate, dihydrostreptomycin sulphate, oxytetracycline, chlorotetracycline, tetracycline, and chloramphenicol, or sulphonamides may also be present. Specifications 853,981 and 863,781 are referred to.