US4684636A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Antiandrogenic sulfonylsteroidopyrazoles and processes for preparation method of use and compositions thereof
Assignee: Sanofi SA
•
Filing: 1986-04-08
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Granted: 1987-08-04
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Expires: 2006-04-08
Abstract
Abstract 1'-Sulfonylsteroido[3,2-c]pyrazoles, for example, (5 alpha ,17 alpha )-1'-(methylsulfonyl)-1'H-pregn-20-yno[3,2-c]pyrazol-17-ol, which are useful as antiandrogenic agents, and processes for preparation, method of use and compositions thereof are disclosed.
Inventors
- 👤 Robert G. Christiansen
- 👤 Malcolm R. Bell
- 👤 John L. Herrmann, Jr.
- 👤 Chester J. Opalka, Jr.
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 10:11
CPC Classifications
C; C07; C07J; C07J41/00; C07J1/00; C07J1/0003; C07J1/0018; C07J1/0022; C07J1/0033; C07J17/00; C07J31/00; C07J31/006; C07J43/00; C07J71/00; C07J71/0036; C07J71/0042; C07J71/0047
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
129 words
A compound having the structural formula ##STR38## wherein X is CH 3 , CH 3 CH 2 , CH 3 CH 2 CH 2 or ClCh 2 ; Y-Z is ##STR39## R 6 is H or CH 3 when Y-Z is CH═C or H when Y-Z is other than CH═C; R 10 is H or CH 3 ; R 17 α taken alone is H, C 3 , CH 2 CH 3 , CH.tbd.CH 2 , C.tbd.CH or C.tbd.CBr; R 17 β taken alone is OH, OCOCHCl 2 , OCOCF 3 , OCH 3 , OCH 2 SCH 3 , OCH 2 SOCH 3 , OCH 2 SO 2 CH 3 or ##STR40## and R 17 α taken together with R 17 β is OCh 2 CH 2 O.
Claim 2
Dependent Claim
129 words
A compound having the structural formula ##STR38## wherein X is CH 3 , CH 3 CH 2 , CH 3 CH 2 CH 2 or ClCh 2 ; Y-Z is ##STR39## R 6 is H or CH 3 when Y-Z is CH═C or H when Y-Z is other than CH═C; R 10 is H or CH 3 ; R 17 α taken alone is H, C 3 , CH 2 CH 3 , CH.tbd.CH 2 , C.tbd.CH or C.tbd.CBr; R 17 β taken alone is OH, OCOCHCl 2 , OCOCF 3 , OCH 3 , OCH 2 SCH 3 , OCH 2 SOCH 3 , OCH 2 SO 2 CH 3 or ##STR40## and R 17 α taken together with R 17 β is OCh 2 CH 2 O.
Claim 3
Dependent Claim
38 words
A compound according to claim 1 wherein X is CH 3 Y-Z is ##STR41## R 6 is H, R 10 is CH 3 , R 17 α is CH 3 or C.tbd.CH and R 17 β is OH.
Claim 4
Dependent Claim
5 words
(5α,17α)-1'-(Methylsulfonyl)-1'H-pregn-20-yno[3,2-c]pyrazol-17-ol according to claim 2.
Claim 5
Dependent Claim
5 words
(5α,17β)-17-Methyl-1'-(methylsulfonyl)-1'H-androstano[3,2-c]pyrazol-17-ol according to claim 2.
Claim 6
Dependent Claim
5 words
(17β)-4,17-Dimethyl-1'-(methylsulfonyl)-1'H-androst-4-eno[3,2-c]pyrazol-17-ol according to claim 2.
Claim 7
Dependent Claim
5 words
(17α)-4-Methyl-1'-(methylsulfonyl)-1H-pregn-4-en-20-yno[3,2-c]pyrazol-17-ol according to claim 2.
Claim 8
Dependent Claim
40 words
The process of preparing a compound according to claim 1 which comprises sulfonylating the corresponding compound having the structural formula ##STR42## with the corresponding compound having the structural formula XSO.sub.2 Q wherein Q is Cl, Br or OSO 2 X.
Claim 9
Dependent Claim
39 words
The process according to claim 7 wherein X is CH 3 , Y-Z is ##STR43## R 6 is H, R 10 is CH 3 , R 17 α is CH 3 or CH.tbd.CH and R 17 β is OH.
Claim 10
Dependent Claim
42 words
The process of preparing a compound according to claim 1 which comprises condensing the corresponding compound having the structural formula ##STR44## with the corresponding compound having the structural formula XSO.sub.2 NHNH.sub.2 wherein R' is CH 3 or CH 3 CH 2 .
Claim 11
Dependent Claim
39 words
The process according to claim 9 wherein X is CH 3 , Y-Z is ##STR45## R 6 is H, R 10 is CH 3 , R 17 α is CH 3 or C.tbd.CH and R 17 β is OH.
Claim 12
Dependent Claim
14 words
The process according to claim 10 wherein R' is CH 3 CH 2 .
Claim 13
Dependent Claim
47 words
The process of preparing a compound according to claim 1 which comprises condensing the corresponding compound having the structural formula ##STR46## with the corresponding compound having the structural formula XSO.sub.2 NHNH.sub.2 wherein R' is CH 3 , CH 3 CH 2 or C 6 H 5 .
Claim 14
Dependent Claim
39 words
The process according to claim 12 wherein X is CH 3 , Y-Z is ##STR47## R 6 is H, R 10 is CH 3 , R 17 α is CH 3 or C.tbd.CH and R 17 β is OH.
Claim 15
Dependent Claim
23 words
The process according to claim 13 wherein Y-Z is ##STR48## R 17 α is C.tbd.CH and R' is C 6 H 5 .
Claim 16
Dependent Claim
27 words
The process for effecting an antiandrogenic response in a mammal which comprises administering to the mammal an antiandrogenically effective amount of a compound according to claim 1.
Claim 17
Dependent Claim
39 words
The process according to claim 15 wherein X is CH 3 , Y-Z is ##STR49## R 6 is H, R 10 is CH 3 , R 17 α is CH 3 or C.tbd.CH and R 17 β is OH.
Claim 18
Dependent Claim
20 words
A composition which comprises an antiandrogenically effective concentration of a compound according to claim 1 and a pharmaceutically acceptable vehicle.
Claim 19
Dependent Claim
39 words
A composition according to claim 17 wherein X is CH 3 , Y-Z is ##STR50## R 6 is H, R 10 is CH 3 , R 17 α is CH 3 or C═CH and R 17 β is OH.
Claim 20
Dependent Claim
1 words
4-Methyl-1'-(methylsulfonyl)-1'H-androst-4-eno[3,2-c]pyrazol-17-one.
Claim 21
Dependent Claim
1 words
4-Methyl-1'-(methylsulfonyl)-1'H-androst-4-eno[3,2-c]pyrazol-17-one.
References Cited (Backward Citations)
US3704295A
Cited
US4297350A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1990-08-03 | 1991-02-02 | 1991-08-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-08-03 | 1995-02-02 | 1995-08-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-08-03 | 1999-02-02 | 1999-08-04 | $7700.00 | Window Closed / Lapsed |