UN PROCEDIMIENTO PARA LA PREPARACION DE NUEVOS ESTEROIDES HALOGENADOS.

摘要

1,244,560. 4,7 - Dichlorosteroids. F. HOFFMANN-LA ROCHE & CO. A.G. 9 June, 1969 [8 Jan., 1969], No. 29012/69. Heading C2U. The invention comprises steroids of formula wherein R 1 is F, Cl, Br or C 1-8 alkyl; Q is oxo, OH, C 2-8 alkanoyloxy or C 2-4 11,21-alkylenedioxy; and M is a structure of formula wherein R 2 is H or F; R 3 is H, OH, C 1-8 alkoxy, C 2-8 alkanoyloxy, COCHF 2 , COCHCl 2 or C 1-8 alkyl; and R 4 is H, C 1-8 alkyl or C 1-8 alkylidene; or R 3 and R 4 together represent a 16α,17α- [11 - (C 1-8 alkyl) - C 1-8 alkylidenedioxy] group; X is a #1 - unsaturation or a 2 - chloro or 1α,2α- methylene substituent; and n is 0 or 1; or M is a structure of formula wherein R 5 is H or C 2-8 alkanoyl; R 6 is H, C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, C 2-8 haloalkenyl or C 2-8 haloalkynyl; R 7 is H or Me; X1 is a #1-unsaturation or a 2-chloro substituent; n is 0 or 1; and Y is CH 2 , CH(#OH), CH(α-OH) or CO; with the proviso that when X1 is a #1 - unsaturation and n is 1, then R 7 is Me; or M is a structure of formula wherein R8 is H, F, Cl or Br; R 9 is H, OH, OPO(OH) 2 , an alkali metal salt of OPO(OH) 2 or C 2-8 alkanoyloxy; R 10 is H, α-OH, C 1-8 alkylidene, α-F, α-Cl, α-CH 2 Cl, α-CH 2 F or α- or #-C 1-8 alkyl; R 11 is OH or C 2-8 alkanoyloxy; or R 10 and R 11 together represent a 16α,17α- [11 - (C 1-8 alkyl) - C 1-8 alkylidenedioxy] group; or R 9 and R 11 together represent a 17α,21- [11 - (C 1-8 alkoxy) - C 1-8 alkylidenedioxy] group; X1 is a #1-unsaturation or a 2-chloro substituent; n is 0 or 1; Z is CO, CH(α-OH), CH(#-OH), CH(α-OSO 2 R 12 ) where R 12 is C 1-8 alkyl or ptolyl, or when R 8 is H and R 9 is other than H, Z may be CH 2 , or when R 8 is Cl Z may be CH(#-CI), or Z and R 8 together represent a -CH = or -CH(α-epoxy) grouping. Preparation of the above compounds is by reaction of chlorine with compounds of formula (wherein M1 is as defined above for M except that no #1-unsaturation may be present) followed when required by conventional conversions of the 3-oxo group into other values of Q defined above and/or by 1,2-dehydrogenation. The inventive compounds are stated to possess progestational, cortieoid, antiinflammatory and thymolytio activities, and may be made up with carriers into pharmaceutical compositions for oral, parenteral and rectal administration.