Benzamide derivatives

Details Benzamide derivatives Benzamide derivatives

1993-08-11

1995-03-07

Dentz, Bernard

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

514299, 514304, 514413, 540585, 546112, 546124, 546130, 546183, 548452, A61K 3146, A61K 3144, C07D45104, C07D45114

Patent

active

053958322

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

The present invention relates to novel benzamide derivatives which have excellent gastrointestinal stimulating activity and antiemetic activity and are useful as medicament for the treatment of gastrointestinal diseases. The present invention further relates to a method for preparing said benzamide derivatives and a pharmaceutical composition useful for the treatment of gastrointestinal diseases comprising said benzamide derivative as an active ingredient.


BACKGROUND ART

Since the development of Metoclopramide (The Merck Index, 11th Edition, 6063) as an antiemetic agent and a gastrointestinal prokinetic agent, various substituted benzamide derivatives having antiemetic activity and gastrointestinal stimulating activity have been provided.
For example, The Merck Index (11th edition, 2344) discloses Clebopride which is a benzamide derivative having a piperidine ring and is useful as antiulcer agent. The Merck Index (11th edition, 2318) discloses Cisapride useful as a gastrointestinal prokinetic agent. These drugs are widely used clinically. In addition, Japanese Patent Unexamined Publication No. (Sho)55-92384 discloses that benzamide derivatives substituted with an azabicyclo ring have antiemetic activity and gastrointestinal stimulating activity and that they are useful as an antiemetic agent and a gastrointestinal prokinetic agent.
However, these substituted benzamide derivatives are not sufficiently useful since they do not have stimulating activity on lower digestive tracts such as the large intestine, although they have stimulating activity on upper digestive tracts such as the stomach. Furthermore, these substituted benzamide derivatives are not satisfactory from a safe standpoint since they sometimes cause adverse reactions such as extrapyramidal syndrome or hyperprolactinemia.
Accordingly, an object of the present invention is to provide medicament for the treatment of gastrointestinal diseases having stimulating activity not only on upper digestive tract but on lower digestive tract and reduced side effects.
The inventors of the present invention conducted various studies to achieve the aforementioned object, and found that novel benzamide derivatives of the present invention have stimulating activity both on upper digestive tract and lower digestive tract. The inventors also found that these novel benzamide derivatives have reduced side effects and are useful as medicament for the treatment of gastrointestinal diseases having excellent selectivity. The present invention was achieved on the basis of these findings.


DISCLOSURE OF THE INVENTION

The present invention provides benzamide derivatives represented by the following formula (I): ##STR2## wherein, R.sup.1 represents a hydrogen atom or a lower alkanoyl group; R.sup.2 represents a hydrogen atom or a halogen atom; R.sup.3 represents a lower alkoxy group; R.sup.4 represents a hydrogen atom or a lower alkyl group; R.sup.5 represents a hydrogen atom, a lower alkyl group, or a lower alkoxy group; A represents C.sub.1 -C.sub.7 alkylene group which may optionally be substituted with a lower alkyl group; X represents a methylene group, an oxygen atom, or a sulfur atom; m represents an integer of from 0 to 3; n represents an integer of from 0 to 3; and p represents an integer of from 0 to 2, or pharmacologically acceptable salts thereof. The benzamide derivatives are useful since they have gastrointestinal stimulating activity.
According to another embodiment of the present invention, a method for preparing said benzamide derivatives is provided.
According to yet another embodiment of the present invention, a pharmaceutical composition useful for the treatment of gastrointestinal diseases which comprises said benzamide derivative as an active ingredient. The pharmaceutical composition is useful as, for example, a gastrointestinal prokinetic agent, an antiemetic agent, an agent for the treatment of irritable bowel syndrome, and agent for the treatment of constipation.


BEST MODE FOR CARRYING OUT THE INVENTION

In the aforementioned

REFERENCES:
patent: 4163789 (1979-08-01), Mauri et al.
patent: 4808624 (1989-02-01), Monkovie et al.
patent: 4877780 (1989-10-01), Vega-Noverola et al.

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