Tetrahydropyridine derivative having substituents on three rings

Details Tetrahydropyridine derivative having substituents on three rings Tetrahydropyridine derivative having substituents on three rings

1994-12-28

1997-04-15

Rotman, Alan L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

514291, C07D49504, C07D47104, A61K 3144

Patent

active

056211031

DESCRIPTION:

BRIEF SUMMARY
CROSS-REFERENCE

This application is a 371 of PCT/JP 92/00460 filed Apr. 10, 1992.


TECHNICAL FIELD

This invention relates to a tetrahydropyridine derivative having substituents on three rings and represented by the following formula (1), which affects the central nerve of mammal and is useful as a psychotropic drug having antianxiety and learning-improvement effects, and an acid addition salt thereof. ##STR2##


BACKGROUND ART

There have been known that the following compounds (1), (2), (3), (4), (5), (6) and (7) are useful as an anxiolytic drug and a psychotropic drug. published Japanese patent application"):
It has been known that a .beta.-carboline-3-carboxylic acid derivative of the following general formula: ##STR3## is useful as a neuroleptic having an antiaggresive action.
Also, it has been known that the following tetrahydropyridine derivatives and pyridine derivatives (2), (3), (4), (5), (6) and (7) have psychotropic effects.
A compound of the following formula: ##STR4## (3) JP-A-63-096188:
A compound of the following formula: ##STR5## (4) JP-A-63-096189:
A compound of the following formula: ##STR6## (5) JP-A-1-100172:
A compound of the following formula: ##STR7## (6) JP-A-2-149583:
A compound of the following formula: ##STR8## (7) WO89-12447:
A compound of the following formula: ##STR9## Further, there have been made many studies on the synthesis of 1,2,3,4-tetrahydrobenzo[b]thieno[2,3-c]pyridine or derivatives thereof as reported, for example, in Gerhard Wolf and Felix Zymalkowski, Arch. Pharm., 279, 309 (1976)] and biochemical studies on the effects of these compounds on the brain, as reported, for example, in Brandley V. Clineschmidt, Duane R. Reiss, Douglas J. Pettibone and Janet L. Robinson, J. Pharmacol. Exp. Ther., 696-708, 235 (3) (1985). However no such a tetrahydropyridine derivative having substituents on three rings as the one of the present invention has been known so far.
It is an object of the present invention to provide a novel tetrahydropyridine derivative having substituents on three rings which is useful as a drug having antianxiety and learning-improvement effects.


DISCLOSURE OF THE INVENTION

The present inventors have conducted extensive studies in order to develop such a compound which is a tetrahydropyridine derivative having substituents on three rings and shows antianxiety and learning-improvement effects. As a result, they have successfully found out that a tetrahydropyridine derivative on three rings having a specific substituent at the 3-position suits the purpose. The present invention has been completed based on this finding.
Accordingly, the present invention provides a tetrahydropyridine derivative having substituents on three rings and represented by the following formula: ##STR10##
(wherein A represents sulfur atom, sulfoxide group or sulfone group; R.sub.1 represents 4-hydroxycyclohexylamino group, 2-hydroxycyclohexylamino group, 4-methylcylcohexylamino group, 2-methylcyclohexylamino group, 4-tert-butylcyclohexylamino group, 4-aminocyclohexylamino group, piperidinoamino group, 1-(4-methylpiperazinyl)amino group, (2,6-dimethylpiperidino)amino group, (1-pyrrolidinyl)amino group, 1-{4-(2-hydroxyethyl)piperazinyl}amino group, 4-(1,2-diethylpyrazolidinyl)amino group, N-cyclohexyl-N-methylamino group, 4-pyridylamino group, phenylamino group, (1-pyrrolinyl)amino group, 4-(1,2,4-triazolyl)amino group, cyclooctylamino group, N-(4-piperidinyl)methylamino group, cyclohexylmethylamino group, 3-pentylamino group, diethylamino group, 1-adamantaneamino group, 3-quinuclidinylamino group, exo-2-norbornaneamino group, 1-(3-chlorophenyl)piperazinyl group, piperonylamino group, 2-methoxybenzylamino group, 3-methoxybenzylamino group, 4-methoxybenzylamino group, 2,3-dimethoxybenzylamino group, 2,4-dimethoxybenzylamino group, 3,4-dimethoxybenzylamino group, 3,5-dimethoxybenzylamino group, 2,4,6-trimethoxybenzylamino group, 3,4,5-trimethoxybenzylamino group, .alpha.-methylbenzylamino group, 4-methylbenzylamino group, 4-(trifluoromethyl)benzylamino group, 4-(isopropyl)benzylamin

REFERENCES:
patent: 5104876 (1992-04-01), Piwinski et al.

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