Thiazole derivatives

Details Thiazole derivatives Thiazole derivatives

1993-04-23

1995-06-13

Gerstl, Robert

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546207, 546278, C07D41706

Patent

active

054244315

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/JP91/01428 , Oct. 18, 1990.
1. Technical Field
The present invention relates to novel thiazole derivatives and pharmaceutically acceptable salts thereof having 5-HT.sub.3 receptor agonist activity, pharmaceutical compositions thereof, and processes for producing the same.
2. Background Art
While it is acknowledged that, roughly classified, there are 4 types of serotonin (5-HT) receptors, the neuronal serotonin (5-HT) receptors located in the primary afferent nerves of the enteric nervous system or of the central nervous system are considered, as of this day, to be 5-HT.sub.3 receptors. Regarding such 5-HT.sub.3 receptors, many compounds having 5-HT.sub.3 receptor antagonist activity have so far been discovered. For example, the compounds described in British Patents 2,125,398, 2,166,726, 2,126,728 and 2,153,821 are known to have such activity. However, there has not been discovered a compound having selective 5-HT.sub.3 receptor agonist activity.


DISCLOSURE OF INVENTION

The inventors of the present invention conducted extensive studies regarding 5-HT.sub.3 receptors, created a variety of compounds and subjected them to a screening. As a result, they discovered that a novel thiazole derivative of the following general formula (I) possesses excellent selective 5-HT.sub.3 receptor agonist activity and accomplished the present invention. The thiazole derivative of the general formula (I) exhibits its action by inducing release of acetylcholine from the efferent nerve endings. It is thought that any 5-HT.sub.3 receptor agonist drug is useful particularly in disorders of the digestive system. ##STR2## (wherein R.sup.1 means a lower alkoxy group, R.sup.2 and R.sup.3 are either such that R.sup.2 means a hydrogen atom and R.sup.3 means a group of the formula --Y--Het (where Y means a single bond or a lower alkylene group and Het means a nitrogen-containing heterocyclic group) or such that R.sup.2 and R.sup..sup.3 combined together mean a group of the formula. ##STR3## (where m and n each means 1 or 2 and R.sup.4 means a lower alkyl group), and X means a group represented by one of the following formulas: --NH--, ##STR4##
It is, therefore, an object of the present invention to provide a thiazole derivative of the above general formula (I) or a pharmaceutically acceptable salt thereof.
Another object of the present invention is to provide a pharmaceutical composition comprising aforementioned derivative or salt, and a pharmaceutically acceptable carrier.
It is still another object of the present invention to provide processes for producing the aforementioned derivative or salt.
The compound of the above general formula (I) is now described in further detail.
Throughout this specification, the term "lower" means, unless otherwise indicated, a straight or branched carbon chain containing 1 to 6 carbon atoms.
Thus, the "lower alkyl group" includes methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, isohexyl and so on. The group meant by "lower alkoxy group" includes methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, isopentyloxy, hexyloxy, isohexyloxy and so on. Furthermore, "lower alkylene group" includes methylene, ethylene, methylmethylene ##STR5## trimethylene, 1-methylethylene ##STR6## 2-methylethylene ##STR7## tetramethylene, 1-methyltrimethylene, 2-methyltrimethylene, 1-ethylethylene, 2-ethylethylene, pentamethylene, 1-methyltetramethylene, 2-methyltetramethylene, 3-methyltetramethylene, 4-methyltetramethylene, hexamethylene and so on.
Moreover, the nitrogen-containing heterocyclic group forming R.sup.3 means a 5- to 6-membered heterocyclic group containing 1 nitrogen atom. Representative species of the heterocyclic group are pyrrolidinyl, pyrrolyl, piperidyl, pyridyl and so on.
The compound of the present invention contains double bonds and may contain asymmetric carbon atoms depending on substituent groups. Therefore, the compound of the present invention include various mixtures of isom

REFERENCES:
patent: 3804849 (1974-04-01), Griss et al.
patent: 4853403 (1989-08-01), Bomann et al.

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