Anti-estrogenic activity of II.beta.-substituted-19-NOR Steroids

A method of inducing anti-estrogenic activity in warm-blooded animals comprising administering to warm-blooded animals an anti-estrogenically effective amount of a compound of the formula ##STR14## wherein R.sub.17 and R'.sub.17 form .dbd.O or R.sub.17 is --OH or acyloxy of an organic carboxylic acid of up to 12 carbon atoms and

• R'.sub.17 is selected from the group consisting of hydrogen and alkyl, alkenyl and alkynyl, said alkyl, alkenyl and alkynyl each having up to 8 carbon atoms and
• wherein said alkyl, alkenyl and alkynyl are optionally substituted by at least one member selected from the group consisting of halogen, --NH.sub.2, alkylamino of 1 to 4 carbon atoms, dialkylamino of 1 to 4 alkyl carbon atoms, amino alkyl of 1 to 6 carbon atoms, dialkylamino alkyl, dialkylaminoalkoxy, free carboxy salified carboxy, carboxy esterified with lower alkyl, alkyl of 1 to 8 carbon atoms, alkyl of 1 to 8 carbon atoms substituted with one or more halogens, acyl of an organic carboxylic acid of up to 6 carbon atoms, acyloxy of an organic carboxylic acid of up to 6 carbon atoms, OH, .dbd.O, --CN, --NO.sub.2, formyl, alkoxy of 1 to 8 carbon atoms, alkylthio of 1 to 8 carbon atoms, carbamoyl, alkenyl of up to 8 carbon atoms, alkyl of up to 8 carbon atoms and phenyl,
• R.sub.3 is selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms, cycloalkyl of up to 8 carbon atoms and acyl of an organic carboxylic acid of up to 12 carbon atoms and
• R.sub.1 and R.sub.2 are each individually selected from the group consisting of hydrogen, alkyl of up to 8 carbon atoms, cycloalkyl of up to 8 carbon atoms, alkyl of 1 to 8 carbon atoms substituted with one or more halogen atoms, a cycloalkyl of up to 8 carbon atoms substituted with one or more halogen atoms, acyl of an organic carboxylic acid of up to 12 carbon atoms, monocarbocyclic aryl and monocarbocyclic aralkyl having to 1 to 6 alkyl carbon atoms,
• wherein said alkyl, cycloalkyl, halogen substituted alkyl, halogen substituted cycloalkyl, monocarbocyclic aryl and monocarbocyolic aralkyl are each optionally substituted with a member selected from the group consisting of halogen, amino, alkylamino, dialkylamino, aminoalkyl, dialkylaminoalkyl, dialkylaminoalkoxy, hydroxyl, free carboxy, carboxy esterified with alkyl of 1 to 4 carbon atoms, salified carboxy, alkyl of 1 to 8 carbon atoms, alkyl of 1 to 8 carbon atoms substituted by one or more halogens, oxo, cyano, nitro, formyl, acyl of an organic carboxylic acid of up to 12 carbon atoms, alkoxy, alkylthio, alkenyl of up to 3 carbon atoms, alkylnyl of up to 3 carbon atoms,s phenyl and phenyl substituted by one or more halogen atoms,
• or R.sub.2 is hydrogen and R.sub.1 is selected from the group consisting of carbamoyl monosubstituted by a member selected from the group consisting of alkyl of 1 to 8 carbon atoms, alkyl of 1 to 8 carbon atoms substituted by one or more halogen atoms, cycloalkyl of up to 8 carbon atoms substituted by one or more halogen atoms, monocarbocyclic aryl and
• wherein said monocarbocyclic aryl and monocarbocyclic aralkyl are each optionally substituted by one ore more halogens or a member aryl and monocarbocyclic aralkyl are each optionally substituted by one or more halogens or a member selected from the group consisting of --NH.sub.2, alkylamino of 1 to 4 carbon atoms, dialkylamino of 1 to 4 carbon atoms, aminoalkyl of 1 to 2 carbon atoms, dialkylamino alkyl of up to 6 carbon atoms, dialkylaminoalkoxy, free carboxy, salified carboxy, carboxy esterified with lower alkyl, alkyl of 1 to 8 carbon atoms, alkyl of 1 to 8 carbon atoms substituted with one or more halogens, acyl of a monocarbocyclic acid of up to 6 carbon atoms, acyloxy of an organic carboxylic acid of up to 6 carbon atoms, OH, .dbd.O, --CN, --NO.sub.2, formyl, alkoxy of 1 to 8 carbon atoms, alkylthio of 1 to 8 carbon atoms, carbamoyl, alkenyl of up to 8 carbon atoms, alkyl of up to 8 carbon atoms and phenyl and phenyl substituted with one or more halogen atoms,
• or R.sub.1 and R.sub.2 form a dialkylaminomethylene of 1 to 4 carbon atoms, or R.sub.1 and R.sub.2 together with the nitrogen to which they are attached form a saturated heterocycle of 5 to 6 ring members optionally containing a heteroatom of sulfur, nitrogen or oxygen optionally substituted with alkyl of 1 to 4 carbon atoms or .dbd.O,
• n is an integer of 1 to 18 or its non-toxic, pharmaceutically acceptable addition salt with a base or acid.