Derivatives of N-phenylbenzamide with anti-ulcer and anti-allerg

Details Derivatives of N-phenylbenzamide with anti-ulcer and anti-allerg Derivatives of N-phenylbenzamide with anti-ulcer and anti-allerg

1991-08-19

1993-08-03

Gersil, Robert

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

514522, 514563, 558393, 562435, 562450, 548253, 564153, C07D25704, A61K 31185, C07C23381, C07C23556

Patent

active

052329372

DESCRIPTION:

BRIEF SUMMARY
The subject of the present invention is original derivatives of N-phenylbenzamide which can be represented by the general formula indicated below: ##STR1## in which R.sub.1 is a cyano, nitro, halogen, hydroxy, C.sub.1 -C.sub.4 alkyl, methoxy or tetrazol-5-yl group R.sub.5 are independently selected from the group consisting of carboxy, methoxycarbonyl, ethoxycarbonyl and the carbamoyl if R.sub.3 is hydrogen, and R.sub.6 is hydrogen or methyl and their pharmaceutically acceptable salts.
These compounds show interesting pharmacological properties in mammals. One of these properties consists of a high degree of regulatory activity on gastric secretion, particularly activity against the secretion of acid when the secretion is stimulated by various agents such as histamine, carbachol and pentagastrin. Another property consists of a protective and healing activity in relation to the gastro-enteric mucous membrane. A further property is that of inhibiting the release of chemical mediators responsible for allergic or immunological reactions. These compounds can thus be used to advantage in the treatment of various disorders in man such as disorders of the digestive system, such as those resulting from gastro-secretory disorders or lesions, that is peptic ulcers, gastro-duodenitis or colitis; or may be used to treat various pathological conditions which can be attributed to hypersensitivity to allergens such as, for example, bronchial asthma, rhinitis, or allergic conjunctivitis or other pathological conditions of other organs or areas.
The method for the preparation of the N-phenylbenzamide derivatives of the invention is characterised by various steps which can be represented as follows: are independently selected from carboxy, methoxycarbonyl, ethoxycarbonyl and carbamoyl groups and the R.sub.3 substituent is hydrogen, reacting 1-R.sub.4 -3-R.sub.5 -5-amino-phenyl wherein R.sub.4 and R.sub.5 have the above meaning in an equimolar ratio with the chloride of the suitably-R.sub.1, R.sub.2 -substituted benzoic acid, in which R.sub.1 and R.sub.2 have the meanings given above, at a temperature of between about -5.degree. C. and about +20.degree. C., preferably about +5.degree. C., in the presence of an alkali metal or alkaline-earth metal hydroxide, carbonate or bicarbonate (which serves both to salify the carboxyl functions of the 5-amino-isophthalic acid and as an acceptor of hydrochloric acid) or in the presence of a tertiary organic base. The acid chloride can be added as it is or dissolved in a solvent miscible with water (e.g. dioxan, acetone, tetrahydrofuran). The reaction time may vary from about half an hour to 24 hours; the reaction can generally be considered to be complete after 12 hours. At this point the reaction mixture is acidified and the desired products are isolated by filtration and purified by crystallisation. are both hydrogen, the R.sub.3 substituent is the tetrazol-5-yl group and in which R.sub.1 and R.sub.2 have the meanings given above, except in the case in which R.sub.1 is the tetrazol-5-yl group, reacting 5-(p-amino-phenyl)-tetrazole with the stoichiometric quantity of the chloride of the suitably-substituted benzoic acid dissolved in a solvent miscible with water, preferably tetrahydrofuran, between about -5.degree. C. and about 20.degree. C., preferably at about +5.degree. C. in the presence of a tertiary organic base. The reaction time may vary from about half an hour to 24 hours; in this case also, the reaction can generally be considered to be complete after 12 hours. The solvent is then evaporated under vacuum, the residue taken up with H.sub.2 O and acidified with dilute HCl. The desired products are isolated by filtration, washed until neutral and purified by crystallisation. substituents are independently selected from carboxy, methoxycarbonyl, ethoxycarbonyl and carbamoyl groups, R.sub.3 is hydrogen, R.sub.2 has the meaning given above and R.sub.1 is a tetrazol-5-yl group, the corresponding compound having the cyano group at R.sub.1 and produced as described in point a) is conver

REFERENCES:
patent: 4703110 (1987-10-01), Shudo
patent: 4927928 (1990-05-01), Shroot

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