Claims
- 1. A compound of the formula or a pharmaceutically acceptable salt thereof, ##STR5## wherein R.sup.1 is hydrogen or fluorine;
- R.sup.2 is hydrogen or fluorine;
- R.sup.3 is hydrogen, lower alkyl, lower alkoxy, halogen or lower alkylenedioxy;
- A is straight or branched lower alkylene having 1 to 6 carbon atoms; and n is 0 or 1,
- provided that at least one of R.sup.1 or R.sup.2 is fluorine.
- 2. The compound as in claim 1 wherein
- R.sup.1 and R.sup.2 are fluorine; and
- R.sup.3 is methoxy or methylenedioxy.
- 3. The compound as in claim 1 wherein
- R.sup.1 is hydrogen;
- R.sup.2 is fluorine; and
- R.sup.3 is methoxy.
- 4. The compound as in claim 1 wherein
- R.sup.1 is fluorine;
- R.sup.2 is hydrogen; and
- R.sup.3 is methoxy.
- 5. 1-[1,2-Bis(4-fluorophenyl)],ethyl-4-[2-(3,4-dimethoxyphenyl) ethyl]piperazine or a pharmaceutically acceptable salt thereof.
- 6. 1-[1-(4-Fluorophenyl)-2-phenyl]ethyl-4-[2-(3,4-dimethoxyphenyl)ethyl]piperazine or a pharmaceutically acceptable salt thereof.
- 7. 1-[2-(4-Fluorophenyl)-1-phenyl]ethyl-4-[2-(3,4-dimethoxyphenyl)ethyl]piperazine or a pharmaceutically acceptable salt thereof.
- 8. 1-[1,2-Bis(4-fluorophenyl)]ethyl-4-[2-(3,4-methylenedioxy)phenoxy]ethyl]piperazine or a pharmaceutically acceptable salt thereof.
- 9. A pharmaceutical composition comprising (i) a compound of the formula (II) as defined in claim 1 or a pharmaceutically acceptable salt thereof in an effective amount for treatment of disorders of the cerebro-neural transmission system and (ii) at least one pharmaceutically acceptable excipient.
- 10. The compound as in claim 1 wherein said R.sup.3 is selected from the group consisting of hydrogen; a lower alkyl selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl and hexyl; a lower alkoxy selected from the group consisting of methoxy, ethoxy, propoxy, isopropoxy, butoxy and hexyloxy; a halogen selected from the group consisting of fluorine, chlorine, bromine and iodine; and a lower alkylenedioxy selected from the group consisting of methylenedioxy and ethylenedioxy; and said salt is selected from the group consisting of a hydroxychloric acid salt, a sulfonic acid salt, a lactic acid salt, a maleic acid salt and an oxalic acid salt.
- 11. The composition as in claim 9 wherein the compound is selected from the group consisting of 1-(1,2-bis(4-fluorophenyl)ethyl-4-(2-(3,4-dimethoxyphenyl)-ethyl)piperazine, 1-(1-4-fluorophenyl)-2-phenyl-4-(2-(3,4-dimethoxyphenyl)ethyl)piperazine,1-(2-(4-fluorophenyl)-1-phenyl)ethyl-4-(2-(3,4-dimethoxyphenyl)ethyl)piperazine and 1-(1,2-bis(4-fluorophenyl)ethyl-4-(2-3,4-methylenedioxy)phenoxyethyl)piperazine.
- 12. The composition as in claim 9 wherein said amount is effective for the treatment of defects of memory, insomnia, depression, schizophrenia or dementia which are disorders of the cerebro-neural transmission system.
- 13. The composition as in claim 9 wherein the amount of said compound is an effective serotonine antagonist effective amount.
- 14. The compound as in claim 2, wherein n is zero.
- 15. The compound as in claim 3, wherein n is zero.
- 16. The compound as in claim 4, wherein n is zero.
- 17. The compound as in claim 2, wherein A is a straight C.sub.2 alkylene.
- 18. The compound as in claim 3, wherein A is a straight C.sub.2 alkylene.
- 19. The compound as in claim 4, wherein A is a straight C.sub.2 alkylene.
Priority Claims (1)
| Number |
Date |
Country |
Kind |
| 1-64148 |
Mar 1989 |
JPX |
|
BACKGROUND OF THE INVENTION
This application is a divisional application of U.S. application Ser. No. '07/486,521, filed Feb. 28, 1990, now U.S. Pat. No. 5,087,627.
Diphenylethylamine derivatives were well recognized analgesic (Japanese Patent Publication 24084/1961 etc.) and especially (-)-N,N-dimethyl-1,2-diphenylethylamine, lefetamine, is known to have an excellent analgesic effect.
Chemical modification of amine moiety was also studied, and diphenylethylpiperazine derivatives were reported in Japanese Patent Publication 33827/1986 to have an analgesic effect. Furthermore, we reported that diphenylethylpiperazine derivatives had a calcium antagonistic effect (Japanese Unexamined Patent Publication 141966/1988). Diphenylethylpiperazine derivatives were already known to have analgesic effect and calcium antagonistic effect, but the other useful pharmacological properties were not known.
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|
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| Entry |
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Divisions (1)
|
Number |
Date |
Country |
| Parent |
486542 |
Feb 1990 |
|
Patent Grant
5153198
