Novel 11 .beta.-alkynylphenyl-10-nor-steroids
AssigneeRoussel Uclaf
InventorsJean-Georges Teutsch, Michel Klich, Daniel Philibert
Life of this patent
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Abstract
Novel 11.beta.-alkynylphenyl-19-nor-steroids of the formula ##STR1## wherein R.sub.1 is alkynyl of 2 to 8 carbon atoms optionally substituted with at least one member of the group consisting of --OH halogen, trialkylsilyl of 1 to 6 alkyl carbon atoms, alkoxy and alkylthio of 1 to 6 carbon atoms and dialkylamino of 1 to 6 alkyl carbon atoms having remarkably antiprogestomimetic and antiglucocorticoidal activity.
Claims21
A compound selected from the group consisting of 11.sup..beta. -alkynylphenyl-19-nor-steroids of the formula ##STR225## wherein R.sub.1 is alkynyl of 2 to 8 carbon atoms optionally substituted with at least one member of the group consisting of --OH, halogen, trialkylsilyl of 1 to 6 alkyl carbon atoms, alkoxy and alkylthio of 1 to 6 carbon atoms and dialkylamino of 1 to 6 alkyl carbon atoms, R.sub.2 is alkyl of 1 to 3 carbon atoms, the A and B rings have a structure selected from the group consisting of ##STR226## individually selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms, Rx is selected from the group consisting of hydrogen, or ORe in which Re is selected from the group consisting of hydrogen, alkyl of 1 to 6 carbon atoms and acyl, R.sub.3 is selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms are aralkyl of 7 to 15 carbon atoms, the group ##STR227## is selected from the group consisting of ##STR228## R.sub.3 and R.sub.4 are individually selected from the group consisting of hydrogen, hydroxy, --OAlk.sub.4, ##STR229## alkyl of 1 to 8 carbon atoms, alkenyl and alknynyl of 2 to 8 carbon atoms, phenyl, benzyl, phenethyl, thienyl, furyl, aralkenyl and aralkynyl, the latter seven being unsubstituted or substituted with at least one member of the group consisting of hydroxy, alkoxy and alkylthio of 1 to 4 carbon atoms, halogen and dialkylamino of 1 to 6 alkyl carbon atoms, Alk.sub.4 and Alk.sub.5 being individually selected from the group consisting of alkyl of 1 to 8 carbon atoms and benzyl or R.sub.3 and R.sub.4 taken together form a member of the group consisting of ##STR230## R.sub.5 and R.sub.6 are hydrogen or alkyl of 1 to 4 carbon atoms, M is hydrogen, lithium, sodium or potassium, R.sub.20 is alkyl of 1 to 8 carbon atoms unsubstituted or substituted with hydroxy, R.sub.17 is selected from the group consisting of hydrogen and acetyl, Z and Y form a group selected from the group consisting of ##STR231## R.sub.7 and R.sub.8 are individually alkyl of 1 to 4 carbon atoms and the wavy lines indicate that R.sub.2, R.sub.7 and R.sub.8 and the --CH.sub.2 -- can be in either possible configuration and their non-toxic, pharmaceutically acceptable salts with acids and bases.
Dependencies are inferred from the claim text.