US4634695A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Steroid derivatives
Assignee: Aventis Pharma SA
•
Filing: 1985-01-22
•
Granted: 1987-01-06
•
Expires: 2005-01-22
Abstract
Abstract Novel 19-nor steroids and 19-nor-D-homo-steroids of the formula ##STR1## wherein R 1 is an organic radical of 1 to 18 carbon atoms containing at least one atom selected from the group consisting of nitrogen, phosphorous and silicon with the atom immediately adjacent to the 11-carbon atom being carbon, R 2 is a hydrocarbon of 1 to 8 carbon atoms, X is selected from the group consisting of a pentagonal ring and a hexagonal ring optionally substituted and optionally containing a double bond, B and C together form a double bond or an epoxy group, the C═A group at position 3 is selected from the group consisting of C═O, ketal, which may be open or closed ##STR2## are selected from the group consisting of alkyl of 1 to 8 carbon atoms and aralkyl of 7 to 15 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts having anti-glucocorticoid activity and a process for their preparation.
Inventors
- 👤 Vesperto Torelli
- 👤 Jean G. Teutsch
- 👤 Daniel Philibert
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 21:10
CPC Classifications
C; C07; C07J; C07J1/00; C07J41/00; C07J41/0005; C07J41/0016; A; A61; A61P; A61P25/00; A61P25/20; A61P3/00; A61P3/08; A61P37/00; A61P37/02; A61P37/04; A61P43/00; A61P5/00; A61P5/38; A61P9/00; A61P9/10; A61P9/12; C07J21/00; C07J21/005; C07J21/006; C07J41/0033; C07J41/0077; C07J41/0083; C07J43/00; C07J43/003; C07J51/00; C07J63/00; C07J63/008; C07J7/00; C07J7/0005; C07J71/00; C07J71/0005; C07J71/001
Claims Analysis
Total Claims: 36
Claim 1
Independent Claim
49 words
A compound selected from the group consisting of 11β-(4-dimethylamino-phenyl)-13β-ethyl-17α-(prop-1-ynyl)-.DELTA. 4 ,9 -gonadiene-17β-ol-3-one, 11β-(4-dimethylamino-phenyl)-17α-(3-hydroxy-prop-1-ynyl)-.DELTA. 4 ,9 -estradiene-17β-ol-3-one, 11β-(4-aminophenyl)-17α-(prop-1-ynyl)-Δ 4 ,9 -estradiene-17β-ol-3-one, 11β-(4-methylamino-phenyl)-17α-(prop-1-ynyl)-Δ 4 ,9 -estradiene-17β-ol-3-one, N-[4-{17α-(prop-1-ynyl)-Δ 4 ,9 -estradiene-17β-ol-3-one-11β-yl}]-phenyl-acetamide, 11β-(4-dimethylamino-phenyl)-19-nor-17α-Δ 4 ,9 -pregnadiene-17β-ol-3-one-20-yne-21-carboxylic acid and its salts with non-toxic, pharmaceutically acceptable cations and their non-toxic, pharmaceutically acceptable acid addition salts.
Claim 2
Dependent Claim
49 words
A compound selected from the group consisting of 11β-(4-dimethylamino-phenyl)-13β-ethyl-17α-(prop-1-ynyl)-.DELTA. 4 ,9 -gonadiene-17β-ol-3-one, 11β-(4-dimethylamino-phenyl)-17α-(3-hydroxy-prop-1-ynyl)-.DELTA. 4 ,9 -estradiene-17β-ol-3-one, 11β-(4-aminophenyl)-17α-(prop-1-ynyl)-Δ 4 ,9 -estradiene-17β-ol-3-one, 11β-(4-methylamino-phenyl)-17α-(prop-1-ynyl)-Δ 4 ,9 -estradiene-17β-ol-3-one, N-[4-{17α-(prop-1-ynyl)-Δ 4 ,9 -estradiene-17β-ol-3-one-11β-yl}]-phenyl-acetamide, 11β-(4-dimethylamino-phenyl)-19-nor-17α-Δ 4 ,9 -pregnadiene-17β-ol-3-one-20-yne-21-carboxylic acid and its salts with non-toxic, pharmaceutically acceptable cations and their non-toxic, pharmaceutically acceptable acid addition salts.
Claim 3
Dependent Claim
23 words
A compound of claim 1 selected from the group consisting of 11β-(4-dimethylamino-phenyl)-13β-ethyl-17α-(prop-1-ynyl)-.DELTA. 4 ,9 -gonadiene-17β-ol-3-one and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 4
Dependent Claim
23 words
A compound of claim 1 selected from the group consisting of 11β-(4-dimethylamino-phenyl)-17α-(3-hydroxy-prop-1-ynyl)-.DELTA. 4 ,9 -estradiene-17β-ol-3-one and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 5
Dependent Claim
23 words
A compound of claim 1 selected from the group consisting of 11β-(4-amino-phenyl)-17α-(prop-1-ynyl)-Δ 4 ,9 -estradiene-17β-ol-3-one and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 6
Dependent Claim
23 words
A compound of claim 1 selected from the group consisting of 11β-(4-methylamino-phenyl)-17α-(prop-1-ynyl)-Δ 4 ,9 -estradiene-17β-ol-3-one and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 7
Dependent Claim
23 words
A compound of claim 1 selected from the group consisting of N-[4-{17α-(prop-1-ynyl)-Δ 4 ,9 -estradiene-17β-ol-3-one-11β-yl}]-phenyl-acetamide and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 8
Dependent Claim
34 words
A compound of claim 1 selected from the group consisting of 11β-(4-dimethylamino-phenyl)-19-nor-17α-Δ 4 ,9 -pregnadiene-17β-ol-3-one 20-yne-21-carboxylic acid and its salts thereof with non-toxic, pharmaceutically acceptable cations and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 9
Dependent Claim
21 words
An antiprogestomimetic composition comprising an antiprogestomimetically effective amount of at least one compound of claim 1 and an inert pharmaceutical carrier.
Claim 10
Dependent Claim
27 words
A composition of claim 8 wherein the compound is selected from the group consisting of 11β-(4-dimethylaminophenyl)-13β-ethyl-17α-(prop-1-ynyl)-.DELTA. 4 ,9 -gonadiene-17β-ol-3-one and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 11
Dependent Claim
27 words
A composition of claim 8 wherein the compound is selected from the group consisting of 11β-(4-dimethylaminophenyl)-17α-(3-hydroxy-prop-1-ynyl)-Δ 4 ,9 -estradiene-17β-ol-3-one and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 12
Dependent Claim
27 words
A composition of claim 8 wherein the compound is selected from the group consisting of 11β-(4-amino-phenyl)-17α-(prop-1-ynyl)-Δ 4 ,9 -estradiene-17β-ol-3-one and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 13
Dependent Claim
28 words
A composition of claim 8 wherein the compound is selected from the group consisting of 11β-(4-methylamino-phenyl)-17α- (prop-1-ynyl)-Δ 4 ,9 -estradiene-17β-ol-3-one and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 14
Dependent Claim
27 words
A composition of claim 8 wherein the compound is selected from the group consisting of N-[4-{17α-(prop-1-ynyl)-Δ 4 ,9 -estradiene-17β-ol-3-one-11β-yl}]-phenyl-acetamide and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 15
Dependent Claim
38 words
A composition of claim 8 wherein the compound is selected from the group consisting of 11β-(4-dimethylaminophenyl)-19-nor-17α-Δ 4 ,9 -pregnadiene-17β-ol-3-one 20-yne-21-carboxylic acid and its salts thereof with non-toxic, pharmaceutically acceptable cations and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 16
Dependent Claim
25 words
A method of inducing menses in warm-blooded animals comprising administering to warm-blooded animals an antiprogestomimetically effective amount of at least one compound of claim 1.
Claim 17
Dependent Claim
27 words
A method of claim 15 wherein the compound is selected from the group consisting of 11β-(4-dimethylaminophenyl)-13β-ethyl-17α-(prop-1-ynyl)-.DELTA. 4 ,9 -gonadiene-17β-ol-3-one and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 18
Dependent Claim
27 words
A method of claim 15 wherein the compound is selected from the group consisting of 11β-(4-dimethylamino-phenyl)-17α-(3-hydroxy-prop-1-ynyl)-.DELTA. 4 ,9 -estradiene-17β-ol-3-one and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 19
Dependent Claim
27 words
A method of claim 15 wherein the compound is selected from the group consisting of 11β-(4-amino-phenyl)-17α-(prop-1-ynyl)-Δ 4 ,9 -estradiene-17β-ol-3-one and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 20
Dependent Claim
27 words
A method of claim 15 wherein the compound is selected from the group consisting of 11β-(4-methylamino-phenyl)-17α-(prop-1-ynyl)-Δ 4 ,9 -estradiene-17β-ol-3-one and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 21
Dependent Claim
27 words
A method of claim 15 wherein the compound is selected from the group consisting of N-[4-{17α-(prop-1-ynyl)-Δ 4 ,9 -estradiene-17β-ol-3-one-11β-yl}]-phenyl-acetamide and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 22
Dependent Claim
39 words
A method of claim 15 wherein the compound is selected from the group consisting of 11β-(4-dimethylamino-phenyl)-19-nor-17α-Δ 4 ,9 -pregnadiene-17β-ol-3-one 20-yne-21 -carboxylic acid and its salts thereof with non-toxic, pharmaceutically acceptable cations and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 23
Dependent Claim
21 words
An antiglucocorticoid composition comprising an antiglucocorticoidally effective amount of at least one compound of claim 1 and an inert pharmaceutical carrier.
Claim 24
Dependent Claim
27 words
A composition of claim 22 wherein the compound is selected from the group consisting of 11β-(4-dimethylaminophenyl)-13β-ethyl-17α-(prop-1-ynyl)-.DELTA. 4 ,9 -gonadiene-17β-ol-3-one and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 25
Dependent Claim
27 words
A composition of claim 22 wherein the compound is selected from the group consisting of 11β-(4-dimethylaminophenyl)-17α-(3-hydroxy-prop-1-ynyl)-Δ 4 ,9 -estradiene-17β-ol-3-one and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 26
Dependent Claim
27 words
A composition of claim 22 wherein the compound is selected from the group consisting of 11β-(4-amino-phenyl)-17α-(prop-1-ynyl)-Δ 4 ,9 -estradiene-17β-ol-3-one and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 27
Dependent Claim
27 words
A composition of claim 22 wherein the compound is selected from the group consisting of 11β-(4-methylamino-phenyl)-17α-(prop-1-ynyl)-Δ 4 ,9 -estradiene-17β-ol-3-one and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 28
Dependent Claim
27 words
A composition of claim 22 wherein the compound is selected from the group consisting of N-[4-{17α-(prop-1-ynyl)-Δ 4 ,9 -estradiene-17β-ol-3-one-11β-yl}]-phenyl-acetamide and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 29
Dependent Claim
38 words
A composition of claim 22 wherein the compound is selected from the group consisting of 11β-(4-dimethylaminophenyl)-19-nor-17α-Δ 4 ,9 -pregnadiene-17β-ol-3-one 20-yne-21-carboxylic acid and its salts thereof with non-toxic, pharmaceutically acceptable cations and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 30
Dependent Claim
26 words
A method of inducing antiglucocorticoid activity in warm-blooded animals comprising administering to warm-blooded animals an antiglucocorticoidally effective amount of at least one compound of claim 1.
Claim 31
Dependent Claim
27 words
A method of claim 29 wherein the compound is selected from the group consisting of 11β-(4-dimethylamino-phenyl)-13β-ethyl-17α-(prop-1-ynyl)-.DELTA. 4 ,9 -gonadiene-17β-ol-3-one and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 32
Dependent Claim
27 words
A method of claim 29 wherein the compound is selected from the group consisting of 11β-(4-dimethylamino-phenyl)-17α-(3-hydroxy-prop-1-ynyl)-.DELTA. 4 ,9 -estradiene-17β-ol-3-one and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 33
Dependent Claim
27 words
A method of claim 29 wherein the compound is selected from the group consisting of 11β-(4-amino-phenyl)-17α-(prop-1-ynyl)-Δ 4 ,9 -estradiene-17β-ol-3-one and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 34
Dependent Claim
27 words
A method of claim 29 wherein the compound is selected from the group consisting of 11β-(4-methylamino-phenyl)-17α-(prop-1-ynyl)-Δ 4 ,9 -estradiene-17β-ol-3-one and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 35
Dependent Claim
27 words
A method of claim 29 wherein the compound is selected from the group consisting of N-[4-{17α-(prop-1-ynyl)-Δ 4 ,9 -estradiene-17β-ol-3-one-11β-yl}]-phenyl-acetamide and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 36
Dependent Claim
38 words
A method of claim 29 wherein the compound is selected from the group consisting of 11β-(4-dimethylamino-phenyl)-19-nor-17α-Δ 4 ,9 -pregnadiene-17β-ol-3-one 20-yne-21-carboxylic acid and its salts thereof with non-toxic, pharmaceutically acceptable cations and its non-toxic, pharmaceutically acceptable acid addition salts.
References Cited (Backward Citations)
US4386085A
Cited
US4447424A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1990-01-05 | 1990-07-07 | 1991-01-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-01-05 | 1994-07-07 | 1995-01-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-01-05 | 1998-07-07 | 1999-01-06 | $7700.00 | Window Closed / Lapsed |