Roussel Uclaf

Martine Gaillard-Kelly

Daniel Philibert

Jean-Georges Teutsch

Francois Goubet

Lucien Nedelec

Francois Nique

A compound of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of --CN, --NO.sub.2 and halogen, R.sub.2 is --CF.sub.3 or halogen, --A--B-- is selected from the group consisting of ##STR2## X is --O-- or --S--, R.sub.3 is selected from the group consisting of hydrogen, alkyl, alkenyl and alkynyl of up to 12 carbon atoms, aryl and aralkyl of up to 12 carbon atoms, all optionally substituted with at least one member of the group consisting of --OH, halogen, --SH, --CN, acyl and acyloxy of up to 7 carbon atoms, --aryl, --O--aryl, --O--aralkyl --S-- aryl of up to 12 carbon atoms the aryl and aralkyl being optionally substituted with a member of the group consisting of halogen, --CF.sub.3, alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl and alkynyloxy with the sulfur being optionally oxidized to sulfone or sulfoxide, free, esterified, amidified or salified carboxy, --NH.sub.2, mono and dialkylamino and heterocyclic of 3 to 6 ring members and containing at least one heteroatom selected from the group consisting of oxygen, sulfur and nitrogen, the alkyl, alkenyl and alkynyl being optionally interrupted with at least one member of the group consisting of oxygen, nitrogen and sulfur optionally oxidized to sulfoxide or sulfone, trialkylsilyl with the alkyl having 1 to 6 carbon atoms and acyl and acyloxy of an organic carboxylic acid of 1 to 7 carbon atoms and Y is --O--, --S-- or --NH--, except the compounds wherein --A--B-- is ##STR3## X is oxygen, R.sub.3 is hydrogen and Y is oxygen or --NH--, R.sub.2 is --CF.sub.3 or halogen and R.sub.1 is --NO.sub.2 or halogen and their non-toxic, pharmaceutically acceptable acid addition salts.

Phenylimidazolidines having antiandrogenic activity

A compound of the formula ##STR1## wherein R.sub.1 is --CN, --NO.sub.2 or halogen, R.sub.2 is --CF.sub.3 or halogen, --A-B-- is of ##STR2## X is --O-- or --S--, R.sub.3 is hydrogen, alkyl, alkenyl or alkynyl of up to 12 carbon atoms, aryl and aralkyl of up to 12 carbon atoms, all optionally substituted by --OH, halogen, --SH, --CN, acyl and acyloxy of up to 7 carbon atoms, --aryl, --O--aryl, --O--aralkyl --S-- aryl of up to 12 carbon atoms the aryl and aralkyl being optionally substituted by halogen, --CF.sub.3, alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl or alkynyloxy with the sulfur being optionally oxidized to sulfone or sulfoxide, free, esterified, amidified or salified carboxy, --NH.sub.2, mono and dialkylamino and heterocyclic of 3 to 6 ring members and containing at least one heteroatom selected from the group consisting of oxygen, sulfur and nitrogen, the alkyl, alkenyl and alkynyl being optionally interrupted by at least one oxygen, nitrogen or sulfur optionally oxidized to sulfoxide or sulfone, trialkylsilyl with the alkyl having 1 to 6 carbon atoms and acyl and acyloxy of an organic carboxylic acid of 1 to 7 carbon atoms and Y is --O--, --S-- or --NH--, except the compounds wherein --A-B-- is ##STR3## X is oxygen, R.sub.3 is hydrogen and Y is oxygen or --NH--, R.sub.2 is --CF.sub.3 or halogen and R.sub.1 is --NO.sub.2 or halogen and their non-toxic, pharmaceutically acceptable acid addition salts.

Compounds of the formula ##STR1## wherein .dbd.X is .dbd.O or ##STR2## R is hydrogen or acyl of an organic carboxylic acid of 1 to 12 carbon atoms, the wavy lines indicate the .alpha.- or .beta.-position, the dotted line in the 17-position indicates the bond is in the .alpha.-position and the dotted lines in the 9'(10') and 11'(12') positions indicate an optional double bond in the 9'(10') position or two optional double bonds in the 9'(10') and 11'(12') positions having progestomimetic and antiestrogenic activity.

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Paris, France

Martine Gaillard-Kelly