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

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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 20:37

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

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

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