Imidazole derivatives and processes for the preparation thereof

Details Imidazole derivatives and processes for the preparation thereof Imidazole derivatives and processes for the preparation thereof

1996-11-13

1997-09-09

Morris, Patricia L.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

5462727, 5462744, 5462751, A61K 31415, A61K 3144, C07D40314

Patent

active

056657382

DESCRIPTION:

BRIEF SUMMARY
FIELD OF THE INVENTION

The present invention relates to novel imidazole derivatives, processes for preparing them and pharmaceutical compositions containing same as active ingredients.


BACKGROUND OF THE INVENTION

Various imidazole derivatives, which can inhibit the action of angiotensin II, have been used for the treatment of hypertension caused by angiotensin II. Angiotensin II is produced by an angiotensin converting enzyme from angiotensin I, which is formed from angiotensinogen by the action of renin. Angiotensin II, which is a potent vasoconstrictor interacting with specific receptors on cell membrane, has been reported to cause hypertension in mammals including human beings.
Many studies have been made to search for an antagonist which inhibits the action of angiotensin II on the receptors of its target cell in order to suppress the elevation of blood pressure. As a result, many imidazole derivatives have been developed (see A. T. Chiu et al., Eur. J. Pharm., 157, 13(1981); P. C. Wong et al., J. Pharmacol. Exp. Ther., 247, 1(1988); and P. C. Wong et al., Hypertension, 13, 489(1989)).
As a representative of these compounds, for example, D. J. Carini et al. reported in J. Med. Chem., 34, 2525(1990) imidazole derivatives of the following formula (A): ##STR2##
Despite these discoveries, however, needs have continued to exist for the development of more effective agents which possess enhanced antagonistic property against angiotensin II.


SUMMARY OF THE INVENTION

Accordingly, it is an object of the present invention to provide novel imidazole derivatives and pharmacologically acceptable salts thereof having an enhanced ability to suppress the activity of angiotensin II.
Another object of the present invention is to provide novel processes for preparing the inventive derivatives.
A further object of the present invention is to provide pharmaceutical compositions containing same as active ingredients.
In accordance with the present invention, there is provided novel imidazole compounds of formula (I) and pharmacologically acceptable salts thereof: ##STR3## wherein: A is a straight, branched or cyclic C.sub.1 -C.sub.6 alkyl group, or OR.sub.1 wherein R.sub.1 is a hydrogen, or a straight, branched or cyclic C.sub.1 -C.sub.6 alkyl radical; above, or --C(.dbd.O)--; R.sub.4, --C(.dbd.O)R.sub.1, --C(.dbd.O)OR.sub.1, --CH(OR.sub.1).sub.2 or --C(.dbd.O)NR.sub.1 R.sub.2 wherein R.sub.1 is the same as defined above, R.sub.2 is, independently of R.sub.1, a hydrogen, or a straight, branched or cyclic C.sub.1 -C.sub.6 alkyl radical, and R.sub.3 and R.sub.4 are independently a straight, branched or cyclic C.sub.1 -C.sub.6 alkyl radical; and radical.


DETAILED DESCRIPTION OF THE INVENTION

Among the compounds of formula (I) of the present invention, preferred are those wherein: --C(.dbd.O)R.sub.1 or --CH(OR.sub.1).sub.2 wherein R.sub.1 and R.sub.2 are independently a hydrogen or a C.sub.1 -C.sub.3 alkyl radical, and R.sub.3 and R.sub.4 are independently a C.sub.1 -C.sub.3 alkyl radical; and radical.
Exemplary compounds of formula (I) of the present invention are: )biphenyl-4-yl)methyl]-3H-imidazol-4-yl}[6-(dimethoxymethyl)-1-oxypyridin- 2-yl]methanone; l-4-yl}(6-formyl-1-oxypyridin-2-yl)methanone; l-4-yl}(6-hydroxymethyl-1-oxypyridin-2-yl)methanone; l-4-yl}[6-(dimethoxymethyl)pyridin-2-yl]methanone; l-4-yl}(6-formylpyridin-2-yl)methanone; l-4-yl}[6-(diethylamino)methyl-1-oxypyridin-2-yl]methanone; l-4-yl}[6-((diethyl)(oxy)amino)methyl-1-oxypyridin-2-yl]methanone; l-4-yl}[6-((diethylamino)methyl)pyridin-2-yl]methanone; l-4-yl}[6-[((diethyl)(oxy)amino)methyl]pyridin-2-yl]methanone; l-4-yl}(6-bromo-1-oxypyridin-2-yl)methanone; l-4-yl}[6-(1-hydroxyethyl)-1-oxypyridin-2-yl]methanone; l-4-yl}(6-acetyl-1-oxypyridin-2-yl)methanone; l-4-yl}(6-methoxycarbonyl-1-oxypyridin-2-yl)methanone; l-4-yl}[5-(dimethoxymethyl)-1-oxypyridin-2-yl]methanone; l-4-yl}(5-formyl-1-oxypyridin-2-yl)methanone; l-4-yl}[5-(dimethoxymethyl)pyridin-2-yl]methanone; l-4-yl}[5-(diethylamino)methyl-1-oxypyridin-2-yl]methanone; l-4-yl}[5-((diethyl)(oxy)am

REFERENCES:
patent: 5138069 (1992-08-01), Carini et al.

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