Title:
4*55 SEKOSUTEROIDORUINOSEIHO
Document Type and Number:
Japanese Patent JPS5175054
Kind Code:
A
Abstract:
1492446 4,5-Seco-pregnanes E R SQUIBB & SONS Inc 15 May 1975 [8 Nov 1974] 20694/75 Headings C2C and C2U The invention comprises compounds of formula (wherein A is -CH = CH 2 , -CH 2 CH 3 or -COCH 3 ; X 1 is H, Cl, Br or F; R 1 is H, OH, OCOR 4 , Cl, F, Br or I; R 2 is H or COR 4 ; R 3 is H, Me or CH 2 ; R 4 is C 1-7 alkyl, phenyl, or phenyl substituted by halo, alkyl or alkoxy; Y is H, Y1 is OH or Y + Y1 = oxo); and their preparation from compounds of formula (wherein X 2 is H or F) by hydration or complete or partial hydrogenation of the acetylenic bond, followed when required by one or more steps selected from: hydrolysis of ester groups; esterification of hydroxyl groups; sulphonation of a 21-hydroxyl group (steroid numbering) followed by reaction with an alkali metal halide (for I; R 1 = halo) or with NaI/glacial AcOH (for I; R 1 =H), and dehydration of a 9α-H-11#-OH compound followed by hydroxyhalogenation of the resulting 9(11)-ene. Compounds VIII supra are obtained from compounds of formula by reaction with p-toluenesulphonylhydrazide, optionally followed by conversion of a compound to a 9α-halo-11#-OH compound via a 9(11)-ene. Intermediates in the above reactions are 21 - mesyloxy - 9 - fluoro - 11#,17 - dihydroxy- 4,5-secopregnane-5,20-dione and 17,21-diacetoxy - 4,5 - secopregn - 9(11) - en - 3 - yne - 5,20- dione. 9 - Fluoro - 11#,17,21-trihydroxypregn - 4 -ene- 3,20-dione#its 11,21-(methyl orthoacetate)# the 17,21-(methyl orthoacetate) of 4#,5-epoxy-9-fluoro- 11#,17,21 - trihydroxy - 5# - pregnane - 3,20- dione (X)# the 17-acetate of X# the 17,21- diacetate of X. Oral antiinflammatory compositions comprise a compound I and a carrier.
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Inventors:
KURISUTOFUAA MITSUCHERU SHIMAR
Application Number:
JP13559475A
Publication Date:
June 29, 1976
Filing Date:
November 08, 1975
Export Citation:
Assignee:
SQUIBB & SONS INC
International Classes:
C07C69/013; A61K31/12; A61K31/21; C07C45/00; C07C49/385; C07C67/00; C07J21/00; C07J71/00; (IPC1-7): A61K31/12; A61K31/22; C07C49/27; C07C69/12