GB1296458A

USPTO Abstract

1296458 17-Monoesters of 17α,21-dihydroxy steroids WARNER-LAMBERT CO 22 June 1970 [26 June 1969] 30198/70 Heading C2U 17-Monoesters of 17α,21-dihydroxy-20-oxo steroids are prepared by hydrolysis of corresponding 17,21-orthoesters in a buffered aqueousorganic medium having a pH of 4-6. Specified buffers are acetic acid/sodium acetate HCl/ sodium citrate, HCl/potassium hydrogen phthalate, NaOH/potassium hydrogen phthalate and HCl/glycine. The reaction temp. is from room temp. to reflux temp. Products which are 9# 11#-epoxides may subsequently be treated with HF to give the corresponding 9α-fluoro- 11#-hydroxy compounds. Products claimed per se are: (1) prednisolone 17 - benzoate, (ii) 17α,21 - dihydroxy - 16#- methyl - 4,9(11) - pregnadiene - 3,20 - dione 17- benzoate, (iii) 17α,21 - dihydroxy - 16#-methyl- 1,4,9(11) - pregnatriene - 3,20 - dione 17 - benzoate and (iv) #<SP>4</SP>- and #<SP>1</SP>'<SP>4</SP>-compounds of formula wherein R is C 1-4 alkyl or phenyl, X is H or F and Y is H, α-Me or #-Me, at least one of X and Y being other than H. Pharmaceutical compositions for the parenteral treatment of inflammatory and allergic conditions comprise prednisolone 17-benzoate and a carrier (see Example 9).