N,N'-disubstituted amide derivatives

Details N,N'-disubstituted amide derivatives N,N'-disubstituted amide derivatives

1994-09-06

1995-09-12

O'Sullivan, Peter

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548468, A61K 31415, A61K 3140, C07D23156, C07D20912

Patent

active

054497876

DESCRIPTION:

BRIEF SUMMARY
SPECIFICATION

This application is a 371 of PCT/JP93/00269 filed Mar. 3, 1993.


TECHNICAL FIELD

The present invention relates to novel N,N'-disubstituted amide derivatives. In more detail, it is concerned with novel N,N'-disubstituted amide derivatives and their pharmaceutically admissible acid addition salts, which show an antagonisic action to 5-HT.sub.3 receptor and which are useful as antiemetics, alimentary tract motor function modulators, antimigraine agents, antipsychotics, anxiolytics, etc., and preparative processes therefor.


BACKGROUND TECHNOLOGIES

So far, as antagonists to 5-HT.sub.3 receptors, those having an azabicyclo ring moiety described in Japanese Unexamined Patent Publication Nos. Sho 58-978, Sho 59-36675, Sho 61-275276, Hei 1-104072 and Hei 1-106882, those having an imidazole ring moiety described in Japanese Unexamined Patent Publication Nos. Sho 60-214784, Sho 63-211279, Hei 2-131485 and Hei 3-2180, and the like are known.
As result of our diligent study for purpose of finding out such compounds having potent and selective antagonistic action to the 5-HT.sub.3 receptor, the inventors of the present invention have found N,N'-disubstituted amide derivatives which satisfy said purpose and have a different chemical structure from that of known compounds, leading to completion of the invention.


DISCLOSURE OF THE INVENTION

The present invention relates to novel compounds represented by a general formula [I] ##STR2## (wherein R.sub.1 denotes a hydrogen atom or lower alkyl group, R.sub.2 and R.sub.3, which may be identical or different, denote respectively a hydrogen atom, lower alkyl group, lower alkenyl group, nonsubstituted or substituted aryl-lower alkyl group, acyl group or lower alkoxycarbonyl group, R.sub.4 denotes a hydrogen atom, lower alkyl group or lower alkoxy group, A denotes CH or N, and n denote 1, 2 or 3).
The addition salts of the compounds represented by the general formula [I] are preferably physiologically admissible salts. For example, their salts with an inorganic acid such as hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, etc. and their salts with an organic acid such as acetic acid, propionic acid, citric acid, lactic acid, maleic acid, fumaric acid, succinic acid, tartaric acid, methanesulfonic acid, etc. can be mentioned.
The compounds of general formula [I] include stereoisomers, optical isomers and mixtures thereof. Moreover, the compounds [I] often exist as their hydrates and solyates, so these hydrates and solyates are also included in the compounds of the present invention.
The terms in this specification will be explained hereinafter.
For "lower alkyl group", a straight- or branched-chains with carbon atoms of 1 to 6 such as methyl group, ethyl, n-propyl, i-propyl, etc. is mentioned.
For "lower alkenyl group" a straight- or branched-chains with carbon atoms of 2 to 6 having a double bond at one or more locations such as vinyl, allyl, etc. is mentioned.
"Nonsubstituted or substituted aryl-lower alkyl group" means one having non-substituted aryl portion or one having aryl portion substituted with 1 to 5 halogen atoms (fluorine, chlorine, bromine or iodine), lower alkyl group, trifluoromethyl group, hydroxyl group, lower alkoxy group, cyano group, amino group, monosubstituted amino group, disubstituted amino group, acylamino group, nitro group, carboxyl group or lower alkoxycarbonyl group.
"Acyl group" means non-substituted or substituted saturated aliphatic carboxylic acid residue such as formyl, acetyl, propionyl and so on.
For "lower alkoxycarbonyl group", one in which its lower alkyl portion is a straight- or branched-chain having carbon atoms of 1 to 6 such as methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, etc. is mentioned.
For "lower alkoxy group", one in which its lower alkyl portion is methyl, ethyl, propyl, butyl, etc. is mentioned.
The compounds of the present invention represented by the general formula [I] can be prepared through following processes.
(Preparative process 1)
They can be prepared by reacting a carboxylic

REFERENCES:
patent: 4558048 (1985-12-01), Bass
patent: 4959375 (1990-09-01), Ward

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