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Details for Patent: 5,491,173

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Details for Patent: 5,491,173

Title: Tri-phenyl alkene derivatives and their preparation and use
Abstract:The invention provides novel compounds of the formula: ##STR1## wherein R.sub.1 and R.sub.2, which can be the same or different are H or OH, R.sub.3 is ##STR2## wherein R.sub.4 and R.sub.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.
Inventor(s): Toivola; Reijo J. (Oulu, FI), Karjalainen; Arto J. (Oulu, FI), Kurkela; Kauko O. A. (Oulu, FI), Soderwall; Marja-Liisa (Oulu, FI), Kangas; Lauri V. M. (Turku, FI), Blanco; Guillermo L. (Oulu, FI), Sundquist; Hannu K. (Kaarina, FI), Kalapudas; Arja (Oulu, FI)
Assignee: Orion-yhtyma Oy (Turku, FI)
Filing Date:Jan 24, 1994
Application Number:08/188,420
Claims:1. A compound of the formula: ##STR45## wherein R.sub.1 and R.sub.2, which can be the same or different are H or OH, R.sub.3 is ##STR46## wherein R.sub.4 and R.sub.5, which can be the same or different are H or an alkyl group of 1 to 4 carbon atoms; provided that when R.sub.1 and R.sub.2 are both hydrogen, then R.sub.3 is not dimethylaminoethoxy; and their non-toxic pharmaceutically acceptable salts or N-oxides and mixtures thereof.

2. 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.

3. 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.

4. A compound according to claim 1 which is 4-chloro-1-(4-hydroxyphenyl)-1-[4-[2-(N,N-dimethylamino]ethoxy]phenyl]-2-p henyl-1-butene (Z) isomer or a non-toxic pharmaceutically acceptable salt thereof.

5. A compound according to claim 1 which is 4-chloro-1-(4-hydroxyphenyl)-1-[4-[2-(N-methylamino]ethoxy]phenyl]-2-pheny l-1-butene (Z) isomer or a non-toxic pharmaceutically acceptable salt thereof.

6. A compound according to claim 1 which is 4-chloro-1,2-bis(4-hydroxyphenyl)-1-[4-[2-(N,N-dimethylamino]-ethoxy]pheny l]-1-butene (Z) isomer or a nontoxic pharmaceutically acceptable salt thereof.

7. 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.

8. 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.

9. 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.

10. A method according to claim 9 in which an anti-oestrogen effect is produced in a subject suffering from an oestrogen-dependent tumour.

11. 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-phen yl-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.

12. A compound according to claim 1 in which R.sub.4 and R.sub.5, which can be the same or different, are selected from the group consisting of H, --CH.sub.3 and C.sub.2 H.sub.5.
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