Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1995-05-08
1996-11-26
Bernhardt, Emily
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
544295, 544354, A61K 31495, A61K 31505, C07D40112, C07D40312
Patent
active
055785964
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/JP93/01589 filed Nov. 4, 1993.
1. Technical Field
The present invention relates to novel 2-alkoxy-5,6,7,8-tetrahydroquinoxaline derivatives, a production method thereof, and a pharmaceutical use thereof. The 2-alkoxy-5,6,7,8-tetrahydroquinoxaline derivatives are useful for preventing and treating motion sickness, space sickness, emesis, dizziness, depression, anxiety, eating disorder, and the like.
2. Background Art
It has been known that compounds having an affinity for a serotonin 1A receptor are useful for preventing and treating motion sickness, space sickness, emesis, dizziness, depression, anxiety, eating disorder, and the like. With respect to such compounds, a number of studies have been made and the results thereof have been reported [see, "Nippon Rinsho (Japanese Journal of Clinical Medicine)" vol. 47, special edition, pp. 1241-1248 (1989); J.P. Feighnev, W.F. Boyer, Psychopathology, 22, 21 (1989); P.R. Saxena, C.M. Villalon, TiPS, 11, 95 (1990); N. Matsuki, et al., Jpn. J. Pharmacol. Suppl., 58, 313 (1992); etc] On the other hand, Unexamined Japanese Patent Application Laid-open Specification No. 63-107968 discloses 2-[2-(4-substituted phenyl-1-piperazinyl)ethoxy]-5,6,7,8-tetrahydroquinoxaline derivatives which have platelet agglutination suppressive, vasodilative and lipoperoxide formation suppressive activities. In this prior art document, however, there is no description with respect to the usefulness of such derivatives for preventing and treating serotonergic neuron-related diseases.
Problems to be Solved by the Invention
It has been desired in the art to develop and provide a compound which exhibits excellent pharmacological activities against serotonergic neuron-related diseases.
Means for Solving the Problems
In order to solve the above-mentioned problems accompanying the prior art compounds or derivatives, the present inventors have synthesized various types of compounds and have examined the compounds with respect to the pharmacological properties thereof. As a result, it has unexpectedly been found that 2-alkoxy-5,6,7,8-tetrahydroquinoxaline derivatives represented by formula (1) below, which have never been reported in any of the literature, exhibit an excellent affinity for a serotonin 1A receptor and excellent pharmacological activities against serotonergic neuron-related diseases. The present invention has been completed, based on the above novel findings.
Accordingly, it is an object of the present invention to provide a novel compound represented by formula (1) or a non-toxic salt thereof ##STR2## wherein R.sup.1 represents a hydrogen atom or a lower alkyl group; R.sup.2 represents a pyridyl group which is unsubstituted or substituted with 1 to 3 substituents each independently selected from the group consisting of a halogen atom, a lower alkyl group, a tri-fluromethyl group, a lower alkoxy group, a carbamoyl group and a cyano group, or a pyrimidinyl group which is unsubstituted or substituted with 1 to 2 substituents each independently selected from the group consisting of a lower alkyl group and a lower alkoxy group; and n is an integer of from 2 to 5.
It is another object of the present invention to provide a method for producing the above-mentioned novel compound represented by formula (1) or a non-toxic salt thereof, which comprises reacting, in an inert solvent, a compound represented by formula (2): ##STR3## wherein R.sup.1 and n are as defined for formula (1) above; and X represents a reactive leaving group, ##STR4## wherein R.sup.2 is as defined for formula (1) above.
It is a further object of the present invention to provide a pharmaceutical composition for treating a serotonergic neuron-related disease, which comprises, as an active ingredient, the above-mentioned novel compound represented by formula (1) or a non-toxic salt thereof.
The compound represented by formula (1) of the present invention (which compound is hereinafter, frequently referred to as "compound (1)") can be produced, for example, by reacting, in an inert solve
REFERENCES:
patent: 4894453 (1990-01-01), Yaso et al.
patent: 5001237 (1991-03-01), Yaso et al.
Matsuki et al., Jpn. J. Pharmacol. Suppl., 58, 313 (1992), p. 313.
Saxena et al., TiPs (Mar. 1990) vol. 11, pp. 95-96.
Feighner et al. (1989), Psychopathology 1989; 22(supp); 21-26.
Hisayama et al. Jap. J. Clin. Med., vol. 46 (Sp.Ed.) (1989) pp. 1241-1248 w/translation (partial).
Mochizuki Daisuke
Watanabe Hideyuki
Yaso Masao
Asahi Kasei Kogyo Kabushiki Kaisha
Bernhardt Emily
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