Verfahren zur Herstellung von 21-Pyrazol-steroiden

• Main Author: PAUL SCHNEIDER,WILLIAM
• Format: Patent
• Language: German
• Published: 13.05.1971
• Subjects: CHEMISTRY; HETEROCYCLIC COMPOUNDS; METALLURGY; ORGANIC CHEMISTRY; STEROIDS

1,159,509. Steroids. UPJOHN CO. 2 Jan., 1967 [4 Feb., 1966], No. 125/67. Heading C2U. The invention comprises compounds of the formula wherein # is a generic expression denoting α- and #-bonds and mixtures thereof; R is hydrogen or the acyl radical of a hydrocarbon carboxylic acid containing from 1-12 carbon atoms, R 1 is hydrogen, C 1 -C 8 alkyl or a pharmacologically acceptable salt cation; X is the methylene radical, the α- or #-hydroxy methylene radical or carbonyl; Z is with the proviso that when Z is the stereoconfiguration at C 3 is #-, but when Z is CH 2 the stereoconfiguration at C 3 is α- or #-, whereupon the stereoconfiguration of the hydrogen atom at C 5 is α- or #-, and a process for the preparation of a compound of the above formula, wherein R is the acyl radical of a C 1 - C 12 hydrocarbon carboxylic acid and R1 is C 1-8 alkyl or a pharmacologically acceptable salt cation, which comprises treating a compound of the formula wherein Ac is the acyl radical of a C 1-12 hydrocarbon carboxylic acid, R1, X and Z are as defined above, with diazomethane. The starting compound may be obtained by subjecting to glyoxalation at the 21-position, e.g. with a sodium alkoxide in an alkanol with a dialkyl oxalate, a compound of the formula to yield the corresponding 21-alkoxyoxalyl-3#- hydroxy - 5 - pregnen - 20 - one and subjecting the latter compound to enol acylation at the 3- and 21-positions. Conversions of the groups R & R1 in the products may be effected by the usual procedures. Pharmaceutical compositions having antiinflammatory, central nervous system depressant and hypoglycemic acitivities and containing the above compounds are administered orally or parenterally.