US5047431A
Expired / Lapsed
US
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1,1,2-triphenylbut-1-ene derivatives
Assignee: Astellas Deutschland GmbH
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Filing: 1990-05-14
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Granted: 1991-09-10
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Expires: 2010-05-14
Abstract
Abstract Novel (E)-1-[4'-(2-alkylaminoethoxy)phenyl]-1- (3'-hydroxyphenyl)-2-phenylbut-1-enes of the general formula ##STR1## wherein R 1 and R 2 may be the same or different, provided that, when R 1 and R 2 are the same, each of them is a methyl or ethyl radical, and when R 1 and R 2 are different, one of them is hydrogen and the other is a methyl or ethyl radical, and the therapeutically compatible salts thereof, have a marked anti-estrogenic effect and are suitable for treating hormone-dependent mammary tumors. The compounds can be prepared by dehydrating carbinols of the general formula ##STR2## wherein R 1 and R 2 may be the same or different, provided that, when R 1 and R 2 are the same, each of them is a methyl or ethyl radical, and when R 1 and R 2 are different, one of them is a benzyl radical and the other is a methyl or ethyl radical; and wherein R 3 is hydrogen or an easily hydrolyzable protecting group, through the action of mineral acid while removing any protecting group present, isolating through crystallization the E-form from the pair of isomers obtained, and removing by hydrogenolysis any benzyl group present. Compositions comprising the subject 1,1,2-triphenylbut-1-ene derivatives are described also. The corresponding novel 1,1,2-triphenylbut-1-ene derivatives having the (Z) configuration are also disclosed.
Inventors
- 👤 Helmut Schickaneder
- 👤 Roland Loser
- 👤 Helmut Grill
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 13:28
CPC Classifications
C; C07; C07D; C07D309/00; C07D309/02; C07D309/08; C07D309/10; C07D309/12; A; A61; A61P; A61P35/00; C07C; C07C45/00; C07C45/45; C07C45/46; C07C45/61; C07C45/67; C07C45/673; C07C45/68; C07C49/00; C07C49/76; C07C49/84; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55
Claims Analysis
Total Claims: 25
Claim 1
Independent Claim
73 words
A compound of the formula 1 ##STR11## having the E configuraiton wherein R 1 and R 2 may be the same or different, provided that, when R 1 and R 2 are the same, each of them is a methyl or ethyl radical, and when R 1 and R 2 are different, one of them is hydrogen and the other is a methyl or ethyl radical; or a non-toxic, pharmaceutically acceptable salt thereof.
Claim 2
Dependent Claim
73 words
A compound of the formula 1 ##STR11## having the E configuraiton wherein R 1 and R 2 may be the same or different, provided that, when R 1 and R 2 are the same, each of them is a methyl or ethyl radical, and when R 1 and R 2 are different, one of them is hydrogen and the other is a methyl or ethyl radical; or a non-toxic, pharmaceutically acceptable salt thereof.
Claim 3
Dependent Claim
11 words
The compound (E)-1-[4'(2-dimethylaminoethoxy)phenyl]-1-(3'-hydroxyphenyl)-b 2phenylbut-1-ene or a non-toxic, pharmaceutically acceptable salt thereof.
Claim 4
Dependent Claim
11 words
The compound (E)-1-[4'(2-dimethylaminoethoxy)phenyl]-1-(3'-hydroxyphenyl)-b 2phenylbut-1-ene or a non-toxic, pharmaceutically acceptable salt thereof.
Claim 5
Dependent Claim
9 words
The compound of claim 1 which is (E)-1-[4'-(2-dimethylaminoethoxy)phenyl]-1-(3'-hydroxyphenyl) -2-phenylbut-1-ene.
Claim 6
Dependent Claim
10 words
The compound (E)-1-[4'(2-diethylaminoethoxy)phenyl]-1-(3'-hydroxyphenyl)-2-phenylbut-1-ene or a non-toxic, pharmaceutically acceptable salt thereof.
Claim 7
Dependent Claim
10 words
The compound (E)-1-[4'(2-diethylaminoethoxy)phenyl]-1-(3'-hydroxyphenyl)-2-phenylbut-1-ene or a non-toxic, pharmaceutically acceptable salt thereof.
Claim 8
Dependent Claim
9 words
The compound of claim 1 which is (E)-1-[4'-(2-diethylaminoethoxy)phenyl]-1-(3'-hydroxyphenyl) 2-phenylbut-1-ene.
Claim 9
Dependent Claim
11 words
The compound (E)-1-(3'-hydroxyphenyl)-1-[4'-(2-methylaminoethoxy)phenyl]-2-phenylbut-1 -ene or a non-toxic, pharmaceutically acceptable salt thereof.
Claim 10
Dependent Claim
11 words
The compound (E)-1-(3'-hydroxyphenyl)-1-[4'-(2-methylaminoethoxy)phenyl]-2-phenylbut-1 -ene or a non-toxic, pharmaceutically acceptable salt thereof.
Claim 11
Dependent Claim
8 words
The compound of claim 1 which is (E)-1(3'-hydroxyphenyl)-1-[4'-(2-methylaminoethoxy)phenyl]-2-phenylbut-1-ene.
Claim 12
Dependent Claim
10 words
The compound (E)-1-[4-ethylaminoethoxy)phenyl]-1-(3'-hydroxyphenyl)-2-phenylbut-1-ene or a non-toxic, pharmaceutically acceptable salt thereof.
Claim 13
Dependent Claim
10 words
The compound (E)-1-[4-ethylaminoethoxy)phenyl]-1-(3'-hydroxyphenyl)-2-phenylbut-1-ene or a non-toxic, pharmaceutically acceptable salt thereof.
Claim 14
Dependent Claim
8 words
The compound of claim 1 which is (E)-1-[4'-ethylaminoethoxy)phenyl]-1-)3'-hydroxyphenyl)-2phenylbut-1-ene.
Claim 15
Dependent Claim
32 words
A composition of matter comprising an antiestrogenically effective amount of or a tumor-inhibiting effective amount of a compound or salt as claimed in claim 1, and a non-toxic, pharmaceutically acceptable carrier therefor.
Claim 16
Dependent Claim
29 words
A composition of matter comprising an anti-estrogenically effective amount or a tumor-inhibiting effective amount of (E)-1-[4'-(2-dimethylaminoethoxy) phenyl]-1-(3'-hydroxyphenyl)-(2-phenylbut-1-ene or pharmaceutically acceptable salt thereof and a non-toxic, pharmaceutically acceptable carrier therefor.
Claim 17
Dependent Claim
29 words
A composition of matter comprising an anti-estrogenically effective amount or a tumor-inhibiting effective amount of (E)-1-[4'-(2-dimethylaminoethoxy) phenyl]-1-(3'-hydroxyphenyl)-(2-phenylbut-1-ene or pharmaceutically acceptable salt thereof and a non-toxic, pharmaceutically acceptable carrier therefor.
Claim 18
Dependent Claim
30 words
A method for elicting an anti-estrogenic response in a mammal which comprises administering to said mammal an anti-estrogenically effective amount of a compound or salt as claimed in claim 1.
Claim 19
Dependent Claim
31 words
A method of treating a mammal having a mammary tumor which comprises administering to said mammal a mammary tumor-inhibiting effective amount of a compound or salt as claimed in claim 1.
Claim 20
Dependent Claim
28 words
A method for elicting an anti-estrogenic response in a mammal which comprises administering to said mammal an anti-estrogenically effective amount of a composition as claimed in claim 10.
Claim 21
Dependent Claim
29 words
A method of treating a mammal having a mammary tumor which comprises administering to said mammal a mammary tumor-inhibiting effective amount of a composition as claimed in claim 10.
Claim 22
Independent Claim
29 words
A method for eliciting an anti-estrogenic response in a mammal which comprises administering to said mammal an anti-estrogenically effective amount of (E) -1-[4'-(2-dimethylaminoethoxy) phenyl]-1-(3'-hydroxyphenyl)-2phenylbut-1-ene or pharmaceutically acceptable salt thereof.
Claim 23
Independent Claim
29 words
A method for eliciting an anti-estrogenic response in a mammal which comprises administering to said mammal an anti-estrogenically effective amount of (E) -1-[4'-(2-dimethylaminoethoxy) phenyl]-1-(3'-hydroxyphenyl)-2phenylbut-1-ene or pharmaceutically acceptable salt thereof.
Claim 24
Independent Claim
30 words
A method of treating a mammal having a mammary tumor which comprises administering to said mammal a mammary tumor inhibiting effective amount of (E)-1-[4'-(2-dimethylaminoethoxy) phenyl]-1-(3'-hydroxyphenyl)-2phenylbut-1-ene or pharmaceutically acceptable salt thereof.
Claim 25
Independent Claim
30 words
A method of treating a mammal having a mammary tumor which comprises administering to said mammal a mammary tumor inhibiting effective amount of (E)-1-[4'-(2-dimethylaminoethoxy) phenyl]-1-(3'-hydroxyphenyl)-2phenylbut-1-ene or pharmaceutically acceptable salt thereof.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1994-09-09 | 1995-03-11 | 1995-09-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1998-09-09 | 1999-03-11 | 1999-09-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2002-09-09 | 2003-03-11 | 2003-09-10 | $7700.00 | Window Closed / Lapsed |