Arylamino pyrimidine compound

Details Arylamino pyrimidine compound Arylamino pyrimidine compound

1995-04-03

1997-03-11

Gupta, Yogendra N.

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

Organic compounds

Nitrogen attached directly or indirectly to the purine ring...

544253, 544284, 544298, 544329, C07D40110

Patent

active

056103034

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

This invention relates to a pyrimidine derivative having both of an excellent selective acetylcholinesterase-inhibiting activity and an excellent selective A type monoamine oxidase-inhibiting activity and useful as an antidepressant and an agent for curing senile dementia, and a salt thereof.


BACKGROUND ART

In senile dementia, acetylcholine in a brain is lacking so that an acetylcholinesterase-inhibiting agent has been studied. For example, as an agent for curing dementia, there have been disclosed 1-benzyl-4-[(5,6-dimethoxy-1-indanon)-2-yl]methylpiperidine, etc. in Japanese Provisional Patent Publication No. 79151/1989 and 1-benzyl-4-[2-(4pyrrolidinobenzoyl)ethyl]piperidine, etc. in Japanese Provisional Patent Publication No. 173867/1991 (U.S. Pat. No. 5,177,087). However, senile dementia is generally accompanied with symptoms such as depression, lowering of volition, etc. so that various symptoms of senile dementia cannot be ameliorated sufficiently only by an acetylcholinesterase-inhibiting agent. On the other hand, depression is related to monoamine (noradrenaline, serotonin), and as an antidepressant having an A type monoamine oxidase-inhibiting activity, there has been known, for example, 4-(4-cyanoanilino)-5,6-dihydro-7H-cyclopenta[d]pyrimidine as disclosed in Japanese Provisional Patent Publication No. 203072/1982 (U.S. Pat. No. 4,450,162).
The present inventors have studied for many years in order to develop a medicine having both of a selective acetylcholinesterase-inhibiting activity and a selective A type monoamine oxidase-inhibiting activity and therefore having a further improved curing effect as an agent for curing senile dementia, and consequently found that a pyrimidine derivative having a specific structure with selective inhibiting activities to both enzymes, to accomplish the present invention.


DISCLOSURE OF THE INVENTION

The present invention is a pyrimidine derivative represented by the formula (I): ##STR2##
(wherein R.sup.1 and R.sup.2 each represent a hydrogen atom, a halogen atom, an amino group, a nitro group, an alkyl group, a lower alkoxy group or a lower alkoxycarbonyl group, or R.sup.1 and R.sup.2 are bonded together to form an alkylene group, and said alkyl group and alkylene group may be substituted by a halogen, hydroxy, a lower alkoxy, a lower alkenyloxy, an aryloxy, an aralkyloxy or an acyloxy.
R.sup.3 represents an aralkyl group or a hetero aromatic ring type-alkyl group and the aryl portion of said aralkyl group and the hetero aromatic ring portion of the hetero aromatic ring type-alkyl group may be substituted by a halogen, amino, alkanoylamino, cyano, nitro, hydroxy, a lower alkyl, a lower alkoxy, an aralkyloxy, an alkylenedioxy, a halogeno-lower alkyl or a halogeno-lower alkoxy.
R.sup.4 represents a hydrogen atom or an acyl group.
R.sup.5 represents a hydrogen atom, a hydroxy group or a lower alkoxy group.
A represents ##STR3## where R.sup.6 represents a hydrogen atom, a halogen atom, a lower alkyl group or a lower alkoxy group, X represents --CH=, --CH=CH--(CH.sub.2).sub.p --, --CH.sub.2 -- or --CH.sub.2 CH.sub.2 --(CH.sub.2).sub.p --, Y represents =CH--(CH.sub.2).sub.p --, --CH.sub.2 --(CH.sub.2).sub.p --, a single bond or a double bond and p represents 0 or 1.
Also, . . . represents a single bond or a double bond, and when . . . represents a double bond or X represents --CH=, or Y represents a double bond, R.sup.5 does not exist) and a salt thereof.
The compounds represented by the above formula (I) are roughly classified into compounds represented by the following formula (II) and formula (III): ##STR4##
(wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, X, Y and . . . have the same meanings as defined above)
As the halogen atom of R.sup.1 and R.sup.2, there may be mentioned fluorine, chlorine, bromine and iodine; as the alkyl group, there may be mentioned a C.sub.1-10 straight or branched alkyl group such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, t-butyl, pentyl, hexyl, heptyl, octyl, nonyl and decyl; as

REFERENCES:
patent: 4450162 (1984-05-01), Kamioka et al.
patent: 4895841 (1990-01-01), Sugimoto et al.
patent: 5100901 (1992-03-01), Sugimoto et al.
patent: 5177087 (1993-01-01), Goto et al.

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