Cyclic iminocarboxylic acid derivatives

Details Cyclic iminocarboxylic acid derivatives Cyclic iminocarboxylic acid derivatives

1980-06-05

1984-05-22

Raymond, Richard

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548533, 424270, 424274, C07D20716, C07D27704

Patent

active

044502753

DESCRIPTION:

BRIEF SUMMARY
FIELD OF THE INVENTION

This invention relates to cyclic iminocarboxylic acid derivatives which are therapeutically useful as antihypertensive agents.


DESCRIPTION OF THE INVENTION

According to the present invention, there is provided a cyclic iminocarboxylic acid derivative of the formula: ##STR2## wherein X.sup.1 and X.sup.2 are each hydrogen, halogen (F, Cl or Br), lower alkoxy (e.g. methoxy or ethoxy), lower alkyl (e.g. methyl or ethyl), trifluoromethyl, nitro, amino, alkylamino (e.g. methylamino, dimethylamino or ethylamino), aralkylamino (e.g. benzylamino, phenethylamino or furfurylamino), acetylamino or ethoxycarbonylamino, Y is --CO-- or --SO.sub.2 --, Z is --CH.sub.2 -- or --S--, and R is hydrogen or lower alkyl (e.g. methyl, ethyl, propyl, isopropyl, butyl or isobutyl).
The compounds of formula (I) can be produced by one of the following Methods I ot IV.


Method I

A method of reacting a compound of the formula: ##STR3## wherein R and Z are as defined above, with a functional derivative of an acid of the formula: ##STR4## wherein X.sup.1, X.sup.2 and Y are as defined above.
The functional derivative of an acid of formula (III) includes an acid halide (e.g. acid chloride or acid bromide), an reactive ester (e.g. methanesulfonic acid ester or toluenesulfonic acid ester) and the like.
The reaction is usually carried out in a solvent such as water, dimethylformamide, dioxane, methylene chloride or chloroform, in the presence of an acid acceptor such as sodium hydrogen carbonate, sodium carbonate, potassium carbonate, sodium hydroxide, potassium hydroxide, triethylamine or pyridine, at room temperature or if necessary under heating or under cooling.


Method II

A method of reacting a compound of the formula: ##STR5## wherein Z is as defined above, with a carboxylic acid of the formula: ##STR6## or a functional derivative thereof, wherein X.sup.1, X.sup.2, Y and R are as defined above.
The functional derivative of a carboxylic acid of formula (V) includes an acid chloride, an acid bromide, an acid anhydride, a mixed acid anhydride which is formed by a conventional reaction of a carboxylic acid of formula (V) with an alkyl halocarbonate (e.g. ethyl chlorocarbonate or isobutyl chlorocarbonate), a sulfonyl halide (e.g. mesyl chloride or tosyl chloride) or an inorganic acid halide (e.g. thionyl chloride, phosphorus oxychloride or phosphorus trichloride), a reactive ester (e.g. p-nitrophenyl ester or polychlorophenyl ester) and the like.
The reaction is usually carried out in a solvent such as methylene chloride, chloroform, ether, benzene, toluene, dioxane, dimethylformamide or water, if necessary in the presence of an acid acceptor such as triethylamine, dimethylaniline, pyridine, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium carbonate, potassium carbonate, sodium hydroxide or potassium hydroxide, at room temperature, if necessary under heating or under cooling.


Method III

A method of reating a compound of the formula: ##STR7## wherein R and Z are as defined above, and Hal is halogen (e.g. Cl or Br), with a compound of the formula: ##STR8## or a metal salt thereof (e.g. sodium salt or potassium salt), wherein X.sup.1 and X.sup.2 are as defined above.
The reaction is usually carried out under the conditions mentioned in Method I.


Method IV

A method of reacting a compound of the formula: ##STR9## wherein R and Z are as defined above, with a compound of formula (VII) mentioned above.
The reaction is usually carried out in a solvent such as ethanol, methylene chloride, dioxane, dimethylformamide, benzene or toluene, at room temperature.
The cyclic iminocarboxylic acid derivatives of formula (I) are present as stereoisomers or as mixtures of these isomers. All of these are within the scope of the present invention. A mixture of the isomers, if desired, may be separated into the individual isomers in a conventional manner such as fractional crystallization or chromatography. When a starting compound is used in an optically active form, compounds of formula (I) can be produced stereo-

REFERENCES:
patent: 4105776 (1978-08-01), Ondetti et al.
patent: 4108886 (1978-08-01), Ondetti et al.
patent: 4192878 (1980-03-01), Ondetti
patent: 4282235 (1981-08-01), Ondetti

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