Verfahren zur Herstellung von Aldehyden der Pregnanreihe und ihrer Derivate

摘要

1298477 Aldehydes of the pregnane series CIBA GEIGY Ltd 12 Dec 1969 [12 Dec 1968 19 Dec 1968 17 Nov 1969] 60691/69 Heading C2U Novel steroids of the formula and their tautomeric #17(20)-enols and acylates thereof (in which R 1 is H(#-OH) or O; X is O, (OH) 2 , (OH)(OR 2 ), (OR 2 ) 2 or -O-R 3 -O- wherein R 2 is an unsubstituted or substituted C 1-8 aliphatic or C 6-8 araliphatic hydrocarbon radical and R 3 is C 1-8 alkylene or C 2-8 alk-1-enylene; the #1 double bond is optional; and Y is H, or in the #1,4 compounds, H or Cl) are prepared by (1) conversion of the corresponding 21-ols to the als or their derivatives by known methods, directly or indirectly; or (2) reaction of the corresponding 9,11#-epoxides with HF or an HF donor to give the 9α-fluoro-11#-ols; or (3) treatment of the corresponding 17α,21- diols or 17α-hydroxy-20-keto-21-tertiary amino pregnanes with an acidic agent in an aqueous or alcoholic solution to give the aldehydes or their hydrates or the diacetals. In the products (a) a #1 double bond may be introduced by chemical or microbiological methods; (b) X groups may be interconverted by standard methods or enol acylates may be formed; (c) a #1 double bond may be hydrogenated; (d) a chlorine atom may be introduced into the 2-position; and (e) an 11#-OH group may be oxidized to an 11-oxo group. The novel steroids are anti-inflammatory agents, and they may be made up into pharmaceutical compositions with suitable carriers.