# US 5,705,494 A · Anti-estrogenic activity of II.beta.-substituted-19-NOR Steroids

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- Number: US 5,705,494 A
- Document ID: US5705494A
- Status: Granted
- Kind: A
- Application number: 08/512,284
- Filed: 1995-08-08
- Granted: 1998-01-06
- Earliest claimed: 1993-06-17
- Assignees: Roussel Uclaf
- Inventors: Francois Nique; Jean-Georges Teutsch; Patrick Van de Velde
- Web page: https://patentgrep.com/patent/US5705494A

## CPC

- C07J 41/0083: {substituted in position 11-beta by an optionally substituted phenyl group not further condensed with other rings}
- A61P 1/00: Drugs for disorders of the alimentary tract or the digestive system
- A61P 3/04: Anorexiants; Antiobesity agents
- A61P 3/08: for glucose homeostasis (pancreatic hormones A61P5/48)
- A61P 3/10: for hyperglycaemia, e.g. antidiabetics
- A61P 5/00: Drugs for disorders of the endocrine system
- A61P 5/26: Androgens
- A61P 5/28: Antiandrogens
- A61P 5/30: Oestrogens
- A61P 5/32: Antioestrogens
- A61P 5/38: of the suprarenal hormones
- A61P 5/42: for decreasing, blocking or antagonising the activity of mineralocorticosteroids
- A61P 5/44: Glucocorticosteroids; Drugs increasing or potentiating the activity of glucocorticosteroids
- A61P 5/46: for decreasing, blocking or antagonising the activity of glucocorticosteroids
- A61P 9/10: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A61P 9/12: Antihypertensives
- A61P 15/00: Drugs for genital or sexual disorders (for disorders of sex hormones A61P5/24); Contraceptives
- A61P 15/04: for inducing labour or abortion; Uterotonics
- A61P 15/08: for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
- A61P 17/00: Drugs for dermatological disorders
- A61P 19/10: for osteoporosis
- A61P 25/20: Hypnotics; Sedatives
- A61P 35/00: Antineoplastic agents
- A61P 37/04: Immunostimulants
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07J 1/0059: {substituted in position 17 by a keto group}
- C07J 41/0072: {the A ring of the steroid being aromatic}
- C07J 43/003: {not condensed}
- C07J: STEROIDS (seco-steroids C07C)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Disclosed is a method of inducing anti-estrogenic activity in warm-blooded animals by the administration of a compound of the formula ##STR1## wherein the substituents are as defined in the specification.

## Claims

### Claim 1

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.

### Claim 2 (depends on 1)

The method of claim 1 wherein the active compound is selected from the group consisting of
N-butyl-5-›4(.DELTA.1,3,5(10)-estratrien-3,17.beta.-diol-11.beta.-yl)-pheno xy!-pentanesulfonamide,
N-butyl-5-›4(.DELTA.1,3,5(10)-estratrien-3,17.beta.-diol-11.beta.-yl)-pheno xy!-N-methyl-pentanesulfonamide,
5-›4(.DELTA.1,3,5(10)-estratrien-3,17.beta.-diol-11.beta.-yl)-phenoxy!-N-(2 ,2,3,3,4,4,4-heptafluorobutyl)-N-methyl-pentanesulfonamide.

### Claim 3 (depends on 1)

The method of claim 1 wherein the compound has the formula ##STR15## wherein R.sub.1 and R.sub.2 are each individually selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms and cycloalkyl, wherein both alkyl and cycloalkyl are optionally halo substituted, acyl of an organic carboxylic acid of 1 to 12 carbon atoms and phenyl which is optionally halo substituted or
R.sub.2 is hydrogen and R.sub.1 is a member selected from the group consisting of carbamoyl optionally substituted with alkyl of 1 to 8 carbon atoms, cycloalkyl of up to 8 carbon atoms optionally halo substituted, acyl of an organic carboxylic acid of up to 12 carbon atoms, phenyl and halo substituted phenyl.