| abstract |
Novel 3-keto-19-nor- DELTA 4,9-steroids of the formula <IMAGE> I wherein R1 is selected from the group consisting of naphthyl, phenylphenyl, alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms optionally containing additional unsaturations, phenoxy, furyl, cycloalkyl of 3 to 6 carbon atoms, thienyl optionally substituted with at least one member of the group consisting of halogen and alkyl and haloalkyl of 1 to 6 carbon atoms and phenyl optionally substituted with at least one member of the group consisting of -OH, halogen, -CF3, alkyl and alkoxy of 1 to 6 carbon atoms, alkenyloxy of 2 to 6 carbon atoms, phenoxy and alkylthio of 1 to 6 carbon atoms optionally oxidized to the sulfoxide or sulfone, R2 is selected from the group consisting of methyl and ethyl, R3 is selected from the group consisting of hydrogen, optionally substituted alkyl of 1 to 6 carbon atoms, optionally substituted alkenyl and alkynyl of 2 to 6 carbon atoms, -OH, acetyl, hydroxyacetyl, carboxyalkoxy of 2 to 4 carbon atoms optionally esterified or salified and hydroxyalkyl of 1 to 6 carbon atoms optionally esterified, R4 is selected from the group consisting of hydrogen, alkylthio and alkoxy of 1 to 12 carbon atoms, trialkylsilyl of 1 to 6 carbon atoms, -CN, -OH and alkyl, alkenyl and alkynyl of up to 12 carbon atoms optionally substituted with at least one member of the group consisting of halogen and alkylamino and dialkylamino of 1 to 6 alkyl carbon atoms, R5 is selected from the group consisting of hydrogen and methyl in the alpha - or beta -position, X is =0 or hydroxyimino or alkoxyimino of 1 to 4 carbon atoms in the syn or anti form and A and B are an epoxy or a second bond in the 9(10) position and their non-toxic, pharmaceutically acceptable acid addition salts where R4 is an amino group, with the proviso that A and B are not a second bond in the 9(10)-position when X is =0 and R5 is hydrogen and a) R2 is methyl and alpha ) R3 is -OH and i) R1 is ethyl or phenyl and R4 is hydrogen or ii) R1 is ethyl, propyl, isopropyl, vinyl, allyl, isopropenyl, phenyl, 4-fluorophenyl, methoxyphenyl or thienyl and R4 is ethynyl or iii) R1 is propyl, isopropyl, vinyl, allyl, isopropenyl, 4-methoxyphenyl or thienyl and R4 is methyl and beta ) R3 is acetyl and i) R1 is ethyl, vinyl or phenyl and R4 is -OH or ii) R1 is vinyl and R4 is methyl and b) R2 is ethyl and R1 is vinyl, R3 is -OH and R4 is hydrogen possessing a remarkable antiglucocorticoidal activity. |