GB814877A - Steroid compounds and the preparation thereof - Google Patents

Abstract

The invention comprises compounds having the formula <FORM:0814877/IV (b)/1> wherein R is a carboxylic acid group preferably having 1-10 carbon atoms or a hydrogen atom and X is bromine, fluorine, or chlorine, a process for the preparation of the 9-bromo derivative thereof by reacting D 4,9(11)-pregnadiene-14a , 17a ,21 - triol - 3,20 - dione - 21 - ester with an N-brom lower alkyl amide or N-bromo dicarboxylic acid amide and specifically N-bromacetamide, N - brompropionamide or N - bromsuccinimide so as to introduce selectively the elements of hypobromous acid at the isolated double bond present at the 9(11)-position of the molecule; and a process for the preparation of the corresponding 9-chloro and 9-fluoro derivatives by contacting D 4 - 9a - halo - 15b -bromopregnene - 11b ,14a ,17a ,21 - tetrol - 3,20-dione-21-ester with Raney nickel. The reaction to obtain the 9-bromo derivative may be effected in the presence of an oxidizing acid such as perchloric acid and a medium consisting of water and a stable water-miscible organic solvent, e.g. dioxane. The dehydrobromination reaction to obtain the 9-chloro and 9-fluoro compounds may be effected in the presence of an inert solvent such as ether, ethyl acetate or dioxane and similar solvents. The products may be hydrolysed to provide the 21-alcohols if desired. Examples described the preparation of D 4-9a bromo and 9a -fluoro-11b ,14a ,17a ,21-tetrol-3,20-dione 21-acetate. Specifications 769,998, 770,000, 814,878, 814,879 and 814,880 are referred to.ALSO:D 4 - 9a - Halo - (especially fluoro) pregnene-11BETA,14a ,17a ,21 - tetrol - 3,20 - dione - 21 - esters, which are highly active as anti-inflammatory agents, may be administered by intra-articular injection, or as an ointment or finely divided suspension to the eyes and other body tissues. Antibiotics may also be incorporated. Specifications 769,998, 770,000, 814,878, 814,879 and 814,880, [all in Group IV (b)], are referred to.