Quinolinoneimine carboxylic acid anti-inflammatory and analgesic

Details Quinolinoneimine carboxylic acid anti-inflammatory and analgesic Quinolinoneimine carboxylic acid anti-inflammatory and analgesic

1981-08-18

1983-12-20

Rivers, Diana G.

Drug, bio-affecting and body treating compositions

Antigen, epitope, or other immunospecific immunoeffector

Bacterium or component thereof or substance produced by said...

546159, 562456, A61K 3147, C07D21554

Patent

active

044217560

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

This invention concerns a novel compound, a production process therefor and an anti-inflammatory and analgesic composition containing the novel compound.


DISCLOSURE OF INVENTION

This invention concerns 1-(2,6-dichlorophenyl)-2-quinolinoneimine-3-carboxylic acid represented by the general formula: ##STR2## a process for producing the same and an anti-inflammatory and analgesic composition containing the novel compound.
The compound of the formula (I) according to this invention can be obtained at high yield by reacting N-(2,6-dichlorophenyl)-anthranylaldehyde represented by the formula ##STR3## with cyanoacetic acid or its ester represented by the general formula ##STR4## wherein R represents hydrogen or lower alkyl group, in particular, methyl, ethyl, propyl or butyl group, then treating with an alkali.
The compound of the formula (I) according to this invention can provide, in admixture with known carrier(s), an anti-inflammatory and analgesic composition showing excellent effects.


BRIEF DESCRIPTION OF DRAWINGS

FIG. 1 is a graph showing the result of an edema test using the compound of formula (I) according to this invention, FIG. 2 is a graph showing the result of an edema test using a commercial pharmaceutical, INDOMETHACIN (IM), and FIG. 3 is a graph showing the result of an edema test using another commercial pharmaceutical DICLOFENAC SODIUM (DF).


BEST MODE FOR CARRYING OUT THE INVENTION

The process for producing the compound of the formula (I) according to this invention is explained below by way of a flow diagram.
The route A is explained in detail at first. ##STR5##
An intermediate 1-(2,6-dichlorophenyl)-3-alkoxycarbonyl-2-quinolinoneimine of the formula (IVa) is obtained through the condensing reaction of N-(2,6-dichlorophenyl)anthranylaldehyde of the formula (II) with a cyanoacetic ester of the formula (IIIa). In the reaction, the compound of the formula (IIIa) is preferably used in 1-3 mol, particularly 1.1-2.0 mol, per one mol of the compound of the formula (II). The catalyst used herein includes a mixture of organic acid salt and acetic acid, for example a mixture of ammonium acetate and acetic acid, a mixture of piperidium acetate and acetic acid, or a mixture of piperidium benzoate and acetic acid, use of the mixture of ammonium acetate and acetic acid being particularly preferred. For the amount of the catalyst, ammonium acetate is used in 0.5-5 mol, preferably 1.0-2.0 mol, and acetic acid is used in 0.5-10 mol, preferably 1.0-4.0 mol, per one mol of the compound of the formula (II). Any solvents inert to the reaction such as benzene, toluene, or xylene may be used, with particular preference being given to the use of such solvents capable of facilitating the reaction while eliminating water resulting from the condensation as azeotropic mixture. The reaction time is about 1-12 hour, preferably about 2-5 hours. The reaction temperature is preferably near the boiling point of the solvent employed.
1-(2,6-dichlorophenyl)-2-quinolinoneimine-3-carboxylic acid (I) which is the desired compound according to this invention can be obtained by hydrolyzing the intermediate (IVa) thus obtained using an alkali. The alkali used in the hydrolyzing reaction may include, for example, alkali metal hydroxide such as potassium hydroxide and sodium hydroxide, alkaline earth metal hydroxide such as calcium hydroxide and barium hydroxide, alkali metal carbonate such as sodium carbonate, and alkali metal hydrogen carbonate such as sodium hydrogen carbonate. Use of the alkali metal hydroxide, especially, potassium hydroxide and sodium hydroxide, is particularly preferred. The amount used is 1-5 mol, preferably 1.2-2 mol per one mol of the compound of the formula (IVa). Any solvents inert to the reaction can be used and they include, for example, methanol, ethanol, propanol, dimethylformamide and dimethylsulfoxide, use of methanol or ethanol being preferred among all. The reaction time is about 1-12 hours, preferably about 2-6 hours. The reaction temperature is about 30.degree.-150.degree.

REFERENCES:
patent: 3542785 (1970-11-01), Carney
patent: 4044134 (1977-08-01), Althuis et al.
patent: 4221797 (1980-09-01), Hardtmann et al.
Nagai, et al., Chemical Abstracts, vol. 70, 67824k (1969).

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