US4233296A
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11β-Substituted-Δ4,9 -estradienes
Assignee: Sanofi Aventis France
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Filing: 1978-01-06
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Granted: 1980-11-11
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Expires: 1998-01-06
Abstract
Abstract Novel steroids of the formula ##STR1## wherein R 1 is linear or branched alkyl of 1 to 12 carbon atoms, unsaturated alkyl of 2 to 8 carbon atoms optionally substituted, optionally substituted aryl of 6 to 12 carbon atoms, optionally substituted aralkyl of 7 to 13 carbon atoms and a heterocycle with at least one sulfur or oxygen atom, R 2 is alkyl of 1 to 4 carbon atoms, R 3 is selected from the group consisting of hydrogen, hydroxy, acyloxy of an organic carboxylic acid of 1 to 18 carbon atoms, alkoxy of 1 to 8 carbon atoms and acyl of an organic carboxylic acid of 1 to 18 carbon atoms and R 4 is selected from the group consisting of hydrogen, hydroxy, alkyl and alkoxy of 1 to 8 carbon atoms, alkenyl and alkynyl of 2 to 8 carbon atoms and acyloxy of an organic carboxylic acid of 1 to 18 carbon atoms, with the proviso that R 4 is not hydrogen when R 1 is allyl, R 2 is methyl and R 3 is hydroxy having progestomimetic properties and their preparation.
Inventors
- 👤 Jean G. Teutsch
- 👤 Daniel Philibert
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 00:15
CPC Classifications
C; C07; C07J; C07J21/00; C07J21/005; C07J21/006; C07J1/00; C07J1/0051; C07J1/0066; C07J1/007; C07J1/0081; C07J1/0085; C07J1/0088; C07J1/0096; C07J33/00; C07J33/002; C07J51/00; C07J7/00; C07J7/0005; C07J7/001; C07J7/004; C07J7/0045; C07J71/00; C07J71/0005; C07J71/001
Claims Analysis
Total Claims: 33
Claim 1
Independent Claim
220 words
A compound of the formula ##STR13## wherein R 1 is linear or branched alkyl of 1 to 12 carbon atoms, unsaturated alkyl of 2 to 8 carbon atoms optionally substituted with a member selected from the group consisting of alkylthio of 1 to 4 carbon atoms and halogens aryl of 6 to 12 carbon atoms and aralkyl of 7 to 13 carbon atoms optionally substituted with at least one member of the group consisting of alkyl and alkoxy of 1 to 4 carbon atoms, halogen and --CF 3 and a heterocycle selected from the group consisting of thienyl, isothienyl and furyl, R 2 is alkyl of 1 to 4 carbon atoms, R 3 is selected from the group consisting of hydrogen, hydroxy, acyloxy of an organic carboxylic acid of 1 to 18 carbon atoms, alkoxy of 1 to 8 carbon atoms and acyl of an organic carboxylic acid of 1 to 18 carbon atoms and R 4 is selected from the group consisting of hydrogen, hydroxy, alkyl and alkoxy of 1 to 8 carbon atoms, alkenyl and alkynyl of 2 to 8 carbon atoms and acyloxy of an organic carboxylic acid of 1 to 18 carbon atoms, with the proviso that R 4 is not hydrogen when R 1 is allyl, R 2 is methyl and R 3 is hydroxy.
Claim 2
Dependent Claim
220 words
A compound of the formula ##STR13## wherein R 1 is linear or branched alkyl of 1 to 12 carbon atoms, unsaturated alkyl of 2 to 8 carbon atoms optionally substituted with a member selected from the group consisting of alkylthio of 1 to 4 carbon atoms and halogens aryl of 6 to 12 carbon atoms and aralkyl of 7 to 13 carbon atoms optionally substituted with at least one member of the group consisting of alkyl and alkoxy of 1 to 4 carbon atoms, halogen and --CF 3 and a heterocycle selected from the group consisting of thienyl, isothienyl and furyl, R 2 is alkyl of 1 to 4 carbon atoms, R 3 is selected from the group consisting of hydrogen, hydroxy, acyloxy of an organic carboxylic acid of 1 to 18 carbon atoms, alkoxy of 1 to 8 carbon atoms and acyl of an organic carboxylic acid of 1 to 18 carbon atoms and R 4 is selected from the group consisting of hydrogen, hydroxy, alkyl and alkoxy of 1 to 8 carbon atoms, alkenyl and alkynyl of 2 to 8 carbon atoms and acyloxy of an organic carboxylic acid of 1 to 18 carbon atoms, with the proviso that R 4 is not hydrogen when R 1 is allyl, R 2 is methyl and R 3 is hydroxy.
Claim 3
Dependent Claim
10 words
A compound of claim 1 wherein R 2 is methyl.
Claim 4
Dependent Claim
10 words
A compound of claim 1 wherein R 2 is ethyl.
Claim 5
Dependent Claim
16 words
A compound of claim 1 wherein R 1 is alkyl of 1 to 12 carbon atoms.
Claim 6
Dependent Claim
30 words
A compound of claim 1 wherein R 1 is alkenyl or alkynyl of 2 to 4 carbon atoms optionally substituted with thioalkyl of 1 to 4 carbon atoms or fluorine.
Claim 7
Dependent Claim
10 words
A compound of claim 1 wherein R 1 is vinyl.
Claim 8
Dependent Claim
26 words
A compound of claim 1 wherein R 1 is phenyl or benzyl optionally substituted on the phenyl ring with alkoxy of 1 to 4 carbon atoms.
Claim 9
Dependent Claim
10 words
A compound of claim 1 wherein R 1 is thienyl.
Claim 10
Dependent Claim
10 words
A compound of claim 1 wherein R 4 is hydrogen.
Claim 11
Dependent Claim
36 words
A compound of claim 1 wherein R 3 is selected from the group consisting of hydroxy, alkoxy of 1 to 8 carbon atoms and acyloxy of an organic carboxylic acid of 1 to 18 carbon atoms.
Claim 12
Dependent Claim
10 words
A compound of claim 1 wherein R 4 is ethynyl.
Claim 13
Dependent Claim
10 words
A compound of claim 1 wherein R 3 is ##STR14##
Claim 14
Dependent Claim
141 words
A compound of claim 1 selected from the group consisting of 11β-methyl-17β-benzoyloxy-Δ 4 ,9 -estradiene-3-one, 11β-ethyl-Δ 4 ,9 -estradiene-17β-ol-3-one, 11β-phenyl-17β-benzoyloxy-Δ 4 ,9 -estradiene-3-one, 11β-phenyl-Δ 4 ,9 -estradiene-17β-ol-3-one, 11β-ethyl-17α-ethynyl-Δ 4 ,9 -estradiene-17β-ol-3-one, 11β-propyl-17α-ethynyl-Δ 4 ,9 -estradiene-17β-ol-3-one, 11β-isopropyl-17α-ethynyl-Δ 4 ,9 -estradiene-17β-ol-3-one, 11β-decyl-17α-ethynyl-Δ 4 ,9 -estradiene-17β-ol-3-one, 11β-vinyl-17α-ethynyl-Δ 4 ,9 -estradiene-17β-ol-3-one, 11β-vinyl-17α-ethynyl-17β-acetoxy-Δ 4 ,9 -estradiene-3-one, 11β-isopropenyl-17α-ethynyl-Δ 4 ,9 -estradiene-17β-ol-3-one, 11β-allyl-17α-ethynyl-Δ 4 ,9 -estradiene-17β-ol-3-one, 11β-benzyl-17α-ethynyl-Δ 4 ,9 -estradiene-17β-ol-3-one, 11β-(p-methoxyphenyl)-17α-ethynyl-Δ 4 ,9 -estradiene-17β-ol-3-one, 11β-(2-thienyl)-17α-ethynyl-Δ 4 ,9 -estradiene-17β-ol-3-one, 11β-(o-methoxyphenyl)-17α-ethynyl-Δ 4 ,9 -estradiene-17β-ol-3-one, 11β-ethyl-17β-acetyl-Δ 4 ,9 -estradiene-17α-ol-3-one, 11β-ethyl-17α-acetoxy-17β-acetyl-Δ 4 ,9 -estradiene-3-one, 11β-phenyl-17β-acetyl-Δ 4 ,9 -estradiene-17α-ol-3-one, 11β-vinyl-17α-methyl-17β-acetyl-Δ 4 ,9 -estradiene-3-one, 11β-vinyl-17β-acetyl-Δ 4 ,9 -estradiene-17α-ol-3-one, 11β-vinyl-17α-acetoxy-17β-acetyl-Δ 4 ,9 -estradiene-3-one, 11β -vinyl-18-methyl-Δ 4 ,9 -estradiene-17β-ol-3-one, 11β-propyl-17α-methyl-Δ 4 ,9 -estradiene-17β-ol-3-one, 11β-isopropyl-17α-methyl-Δ 4 ,9 -estradiene-17β-ol-3-one, 11β-decyl-17α-methyl-Δ 4 ,9 -estradiene-17β-ol-3-one, 11β-isopropenyl-17α-methyl-Δ 4 ,9 -estradiene-17β-ol-3-one, 11β-allyl-17β-allyl-17α-methyl-Δ 4 ,9 -estradiene-17β-ol-3-one, 11β-vinyl-17α-methyl-Δ 4 ,9 -estradiene-17β-ol-3-one, 11β-(p-methoxyphenyl)-17α-methyl-Δ 4 ,9 -estradiene-17β-ol-3-one, 11β-benzyl-17α-methyl-Δ 4 ,9 -estradiene-17β-ol-3-one and 11β-(2-thienyl)-17α-methyl-Δ 4 ,9 -estradiene-17β-ol-3-one.
Claim 15
Dependent Claim
20 words
A compound of claim 1 selected from the group consisting of 11β-(p-fluorophenyl)-17α-ethynyl-Δ 4 ,9 -estradiene-17β-ol-3-one and 11β-phenyl-17α-ethynyl-Δ 4 ,9 -estradiene-17β-ol-3-one.
Claim 16
Dependent Claim
21 words
A progestomimetic composition comprising a progestomimetically effective amount of at least one compound of claim 1 and an inert pharmaceutical carrier.
Claim 17
Dependent Claim
10 words
A composition of claim 15 wherein R 2 is methyl.
Claim 18
Dependent Claim
10 words
A composition of claim 15 wherein R 2 is ethyl.
Claim 19
Dependent Claim
16 words
A composition of claim 15 wherein R 1 is alkyl of 1 to 12 carbon atoms.
Claim 20
Dependent Claim
31 words
A composition of claim 15 wherein R 1 is alkenyl or alkynyl of 2 to 4 carbon atoms optionally substituted with thioalkyl of 1 to 4 alkyl carbon atoms or fluorine.
Claim 21
Dependent Claim
10 words
A composition of claim 15 wherein R 1 is vinyl.
Claim 22
Dependent Claim
26 words
A composition of claim 15 wherein R 1 is phenyl or benzyl optionally substituted on the phenyl ring with alkoxy of 1 to 4 carbon atoms.
Claim 23
Dependent Claim
10 words
A composition of claim 15 wherein R 1 is thienyl.
Claim 24
Dependent Claim
10 words
A composition of claim 15 wherein R 4 is hydrogen.
Claim 25
Dependent Claim
36 words
A composition of claim 15 wherein R 3 is selected from the group consisting of hydroxy, alkoxy of 1 to 8 carbon atoms and acyloxy of an organic carboxylic acid of 1 to 18 carbon atoms.
Claim 26
Dependent Claim
10 words
A composition of claim 15 wherein R 4 is ethynyl.
Claim 27
Dependent Claim
10 words
A composition of claim 15 wherein R 3 is ##STR15##
Claim 28
Dependent Claim
144 words
A composition of claim 15 when the compound is selected from the group consisting of 11β-methyl-17β-benzoyloxy-Δ 4 ,9 -estradiene-3-one, 11β-ethyl-Δ 4 ,9 -estradiene-17β-ol-3-one, 11β-phenyl-17β-benzoyloxy-Δ 4 ,9 -estradiene-3-one, 11β-phenyl-Δ 4 ,9 -estradiene-17β-ol-3-one, 11β-ethyl-17α-ethynyl-Δ 4 ,9 -estradiene-17β-ol-3-one, 11β-propyl-17α-ethynyl-Δ 4 ,9 -estradiene-17β-ol-3-one, 11β-isopropyl-17α-ethynyl-Δ 4 ,9 -estradiene-17β-ol-3-one, 11β-decyl-17α-ethynyl-Δ 4 ,9 -estradiene-17β-ol-3-one, 11β-vinyl-17α-ethynyl-Δ 4 ,9 -estradiene-17β-ol-3-one, 11β-vinyl-17β-ethynyl-17β-acetoxy-Δ 4 ,9 -estradiene-3-one, 11β-isopropenyl-17α-ethynyl-Δ 4 ,9 -estradiene-17β-ol-3-one, 11β-allyl-17α-ethynyl-Δ 4 ,9 -estradiene-17β-ol-3-one, 11β-benzyl-17β-benzyl-17α-ethynyl-Δ 4 ,9 -estradiene-17β-ol-3-one, 11β-(p-methoxyphenyl)-17α-ethynyl-Δ 4 ,9 -estradiene-17β-ol-3-one, 11β-(2-thienyl)-17α-ethynyl-Δ 4 ,9 -estradiene-17β-ol-3-one, 11β-(o-methoxyphenyl)-17α-ethynyl-Δ 4 ,9 -estradiene-17β-ol-3-one, 11β-ethyl-17β-acetyl-Δ 4 ,9 -estradiene-17α-ol-3-one, 11β-ethyl-17α-acetoxy-17β-acetyl-Δ 4 ,9 -estradiene-3-one, 11β-phenyl-17β-acetyl-Δ 4 ,9 -estradiene-17α-ol-3-one, 11β-vinyl-17α-methyl-17β-acetyl-Δ 4 ,9 -estradiene-3-one, 11β-vinyl-17β-acetyl-Δ 4 ,9 -estradiene-17α-ol-3-one, 11β-vinyl-17α-acetoxy-17β-acetyl-Δ 4 ,9 -estradiene-3-one, 11β-vinyl-18-methyl-Δ 4 ,9 -estradiene-17β-ol-3-one, 11β-propyl-17α-methyl-Δ 4 ,9 -estradiene-17β-ol-3-one, 11β-isopropyl-17α-methyl-Δ 4 ,9 -estradiene-17β-ol-3-one, 11β-decyl-17α-methyl-Δ 4 ,9 -estratiene-17β-ol-3-one, 11β-isopropenyl-17α-methyl-Δ 4 ,9 -estradiene-17β-ol-3-one, 11β-allyl-17α-methyl-Δ 4 ,9 -estradiene-17β-ol-3-one, 11β-vinyl-17α-methyl-Δ 4 ,9 -estradiene-17β-ol-3-one, 11β-(p-methoxyphenyl)-17α-methyl-Δ 4 ,9 -estradiene-17β-ol-3-one, 11β-benzyl-17α-methyl-Δ 4 ,9 -estradiene-17β-ol-3-one and 11β-(2-thienyl)-17α-methyl-Δ 4 ,9 -estradiene-17β-ol-3-one.
Claim 29
Dependent Claim
24 words
A composition of claim 15 when the compound is selected from the group consisting of 11β-vinyl-17α-methyl-17β-acetyl-Δ 4 ,9 -estradiene-3-one and 11β-vinyl-17β-acetoxy-17β-acetyl-Δ 4 ,9 -estradiene-3-one.
Claim 30
Dependent Claim
26 words
A method of inducing progestomimetic activity in warm-blooded animals comprising administering to warm-blooded animals a progestomimetically effective amount of at least one compound of claim 1.
Claim 31
Dependent Claim
22 words
The method of claim 29 wherein the compound has acetoxy or ethynyl in the 17α-position and hydroxy or acetyl in the 17β-position.
Claim 32
Dependent Claim
13 words
The method of claim 29 wherein the compound is 11β-vinyl-17α-methyl-17β-acetyl-Δ 4 ,9 -estradiene-3-one.
Claim 33
Dependent Claim
13 words
The method of claim 29 wherein the compound is 11β-vinyl-17α-acetoxy-17β-acetyl-Δ 4 ,9 -estradiene-3-one.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-11-11 | 1984-05-12 | 1984-11-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-11-11 | 1988-05-12 | 1988-11-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-11-11 | 1992-05-12 | 1992-11-11 | $7700.00 | Window Closed / Lapsed |