1,4-Dihydropyridine-3,5-dicarboxylic acid ester derivatives

Details 1,4-Dihydropyridine-3,5-dicarboxylic acid ester derivatives 1,4-Dihydropyridine-3,5-dicarboxylic acid ester derivatives

1982-06-01

1983-12-27

Rotman, Alan L.

Drug, bio-affecting and body treating compositions

Antigen, epitope, or other immunospecific immunoeffector

Parasitic organism or component thereof or substance...

546321, C07D21355, A61K 3144

Patent

active

044230524

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD AND DISCLOSURE OF INVENTION

This invention relates to novel 1,4-dihydropyridine-3,5-dicarboxylic acid ester derivatives represented by the formula ##STR2## and the salts thereof both useful as pharmaceuticals and also concerns with processes for preparing them.
The symbols in the formula previously given each represent the following.
Ar.sup.1 and Ar.sup.2 are each the same or different and represent an aryl group (such as a phenyl group or a phenyl group having 1 to 3 substituents which are each the same or different and which include a halogen atom such as fluorine, bromine, chlorine, iodine or the like; a lower alkyl group such as methyl, ethyl, propyl, isopropyl, butyl or the like; a lower alkoxy group such as methoxy, ethoxy, propoxy, isopropoxy, butoxy or the like; a hydroxyl group; a nitro group; a cyano group; a methylenedioxy group; a trihalomethyl group such as trifluoromethyl, tribromomethyl, trichloromethyl or the like; a lower alkylamino group such as dimethylamino, diethylamino, dibutylamino or the like; a lower alkylthio group such as methylthio, ethylthio, propylthio, isopropylthio or the like; or a lower alkylsulfonyl group such as methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl or the like.
R.sup.1 represents a lower alkyl group (such as methyl, ethyl, propyl, isopropyl, butyl or the like).
R.sup.2 and R.sup.3 are each the same or different and represent a lower alkyl group (such as mentioned for R.sup.1) or an aralkyl group (benzyl, phenethyl or the like optionally substituted with a halogen atom, a lower alkoxy group or the like on benzene ring such as benzyl, parafluorobenzyl, parachlorobenzyl, paramethoxybenzyl, 3,4-dichlorobenzyl, phenethyl, parachlorophenethyl, paramethoxyphenethyl, 3,4-dimethoxyphenethyl, etc.).
n is 1 or 2.
R.sup.4 represents a lower alkyl group (such as mentioned for R.sup.1).
According to the present invention, the compounds having the formula (I) are prepared, for examples, by any of the following processes.
Process 1
This process comprises reacting a compound of the formula: ##STR3## wherein the symbols are as defined above, with a compound of the formula: ##STR4## wherein R.sup.1 is as defined above and R.sup.4 is a lower alkyl group.
This reaction is carried out by mixing together the compounds of the formulae (II), (III) and (IV) and heating the mixture in the presence of an adequate solvent (such as methanol, ethanol, propanol, isopropanol, dioxane, benzene, toluene, acetonitrile, dimethylformamide, dimethylsulfoxide or the like). The compound of the formula (IV) can be prepared, for example, by reacting a compound of the formula R.sup.1 --COCH.sub.2 COOR.sup.4 with ammonia. The compound of the formula (IV) is reacted, after or without isolation, with the compounds of the formulae (II) and (III), thereby producing the compound of the formula (I).
Process 2
This process comprises reacting a compound of the formula ##STR5## wherein the symbols are as defined above, with the compound of the formula (III) and a compound of the formula:
This reaction is conducted by mixing together the compounds of the formulae (V), (III) and (VI) and heating the mixture in the presence of a suitable solvent (such as mentioned above). The compound (V) can be prepared, for instance, by reacting the compound of the formula (II) with ammonia. The compound of the formula (V) is reacted, after or without isolation, with the compounds of the formulae (III) and (VI), thereby producing the compound of the formula (I).
Process 3
The process comprises reacting the compound of the formula (II) with the compound of the formula (III), and reacting the resulting compound of the formula: ##STR6## wherein the symbols are as defined above, with the compound of the formula (IV).
The reaction is effected by heating the compounds of the formulae (IV) and (VII) in the presence of a suitable solvent (such as mentioned above). The compound of the formula (VII) is reacted, after or without isolation, with the compound of the formula (IV).
Process 4
This process compris

REFERENCES:
patent: 3985758 (1976-10-01), Murakami et al.
patent: 3996234 (1976-12-01), Araki et al.

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