US5491173A
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US
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Tri-phenyl alkene derivatives and their preparation and use
Assignee: Farmos Yhtyma Oy
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Filing: 1994-01-24
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Granted: 1996-02-13
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Expires: 2014-01-24
Abstract
Abstract The invention provides novel compounds of the formula: ##STR1## wherein R 1 and R 2 , which can be the same or different are H or OH, R 3 is ##STR2## wherein R 4 and R 5 , which can be the same or different are H or an alkyl group of 1 to 4 carbon atoms, and their non-toxic pharmaceutically acceptable salts and esters and mixtures thereof, which compounds include metabolites of toremifene and exhibit valuable pharmacological properties as oestrogenic, anti-oestrogenic, and progestanic agents.
Inventors
- 👤 Reijo J. Toivola
- 👤 Arto J. Karjalainen
- 👤 Kauko O. A. Kurkela
- 👤 Marja-Liisa Soderwall
- 👤 Lauri V. M. Kangas
- 👤 Guillermo L. Blanco
- 👤 Hannu K. Sundquist
- 👤 Arja Kalapudas
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 03:43
CPC Classifications
C; C07; C07D; C07D295/00; C07D295/04; C07D295/08; C07D295/084; C07D295/088; C07C; C07C29/00; C07C29/09; C07C29/095; C07C309/00; C07C33/00; C07C33/26; C07C33/28; C07C39/00; C07C39/12; C07C39/205; C07C39/21; C07C39/24; C07C39/367; C07C39/373; C07C43/00; C07C43/02; C07C43/03; C07C43/14; C07C43/178; C07C43/1782; C07C43/20; C07C43/225; C07C43/23; C07D307/00; C07D307/02; C07D307/04; C07D307/06; C07D307/10; C07D307/12; C07D307/14; C07D309/00; C07D309/02; C07D309/04; C07D309/08; C07D309/10; C07D309/12
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
82 words
A compound of the formula: ##STR45## wherein R 1 and R 2 , which can be the same or different are H or OH, R 3 is ##STR46## wherein R 4 and R 5 , which can be the same or different are H or an alkyl group of 1 to 4 carbon atoms; provided that when R 1 and R 2 are both hydrogen, then R 3 is not dimethylaminoethoxy; and their non-toxic pharmaceutically acceptable salts or N-oxides and mixtures thereof.
Claim 2
Dependent Claim
82 words
A compound of the formula: ##STR45## wherein R 1 and R 2 , which can be the same or different are H or OH, R 3 is ##STR46## wherein R 4 and R 5 , which can be the same or different are H or an alkyl group of 1 to 4 carbon atoms; provided that when R 1 and R 2 are both hydrogen, then R 3 is not dimethylaminoethoxy; and their non-toxic pharmaceutically acceptable salts or N-oxides and mixtures thereof.
Claim 3
Dependent Claim
17 words
A compound according to claim 1 which is 4-chloro-1,2-diphenyl-1-[4-[2-(N-methylamino)ethoxy]phenyl]-1-butene, (Z)-isomer, or a non-toxic pharmaceutically acceptable salt thereof.
Claim 4
Dependent Claim
17 words
A compound according to claim 1 which is 4-chloro-1,2-diphenyl-1-[4-(aminoethoxy)phenyl]-1-butene (Z)-isomer or a non-toxic pharmaceutically acceptable salt thereof.
Claim 5
Dependent Claim
18 words
A compound according to claim 1 which is 4-chloro-1-(4-hydroxyphenyl)-1-[4-[2-(N,N-dimethylamino]ethoxy]phenyl]-2-phenyl-1-butene (Z) isomer or a non-toxic pharmaceutically acceptable salt thereof.
Claim 6
Dependent Claim
18 words
A compound according to claim 1 which is 4-chloro-1-(4-hydroxyphenyl)-1-[4-[2-(N-methylamino]ethoxy]phenyl]-2-phenyl-1-butene (Z) isomer or a non-toxic pharmaceutically acceptable salt thereof.
Claim 7
Dependent Claim
18 words
A compound according to claim 1 which is 4-chloro-1,2-bis(4-hydroxyphenyl)-1-[4-[2-(N,N-dimethylamino]-ethoxy]phenyl]-1-butene (Z) isomer or a nontoxic pharmaceutically acceptable salt thereof.
Claim 8
Dependent Claim
18 words
A compound according to claim 1 which is 4-chloro-1,2-diphenyl-1-[4-[2-(N,N-diethylamino]ethoxy]phenyl]-1-butene (Z) isomer or a non-toxic pharmaceutically acceptable salt thereof.
Claim 9
Dependent Claim
36 words
A pharmaceutical composition comprising an amount effective to produce an oestrogenic, anti-oestrogenic or progestanic effect of a compound according to claim 1 or a non-toxic pharmaceutically acceptable salt thereof, and a pharmaceutically compatible acceptable carrier therefor.
Claim 10
Dependent Claim
48 words
A method of producing an oestrogenic, anti-oestrogenic or progestanic effect in a subject in which such an effect is desired which comprises administering to said subject a compound according to claim 1, or a non-toxic pharmaceutically acceptable salt thereof in an amount sufficient to produce the desired effect.
Claim 11
Dependent Claim
21 words
A method according to claim 9 in which an anti-oestrogen effect is produced in a subject suffering from an oestrogen-dependent tumour.
Claim 12
Dependent Claim
38 words
A compound according to claim 1 which is selected from the group consisting of 4-chloro-1,2-diphenyl-1-[4-[2-(N-methylamino)-ethoxy]phenyl]-1-butene, (Z)-isomer; 4-chloro-1,2-diphenyl-1-[4-(aminoethoxy) phenyl]-1-butene (Z)-isomer; 4-chloro-1-(4-hydroxyphenyl)-1-[4-[2-(N,N-dimethylamino)-ethoxy]phenyl]-2-phenyl-1-butene, (Z) isomer; 4-chloro-1-(4-hydroxyphenyl)-1-[4-[2-(N-methylamino)-ethoxy]phenyl]-2-phenyl-1-butene, (Z) isomer; 4-chloro-1,2-bis (4-hydroxyphenyl)-1-[4-[2-(N,N-dimethylamino)ethoxy]phenyl]-1-butene, (Z) isomer; 4-chloro-1,2-diphenyl-1-[4[2-(N,N-diethylamino)-ethoxy]phenyl]-1-butene (Z) isomer; and nontoxic pharmaceutically acceptable salts thereof.
Claim 13
Dependent Claim
37 words
A compound according to claim 1 in which R 4 and R 5 , which can be the same or different, are selected from the group consisting of H, --CH 3 and C 2 H 5 .
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1999-02-12 | 1999-08-14 | 2000-02-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2003-02-12 | 2003-08-14 | 2004-02-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2007-02-12 | 2007-08-14 | 2008-02-13 | $7700.00 | Window Closed / Lapsed |