Kissei Pharmaceutical Co., Ltd.

Ono Pharmaceutical Co., Ltd.

Nitten Ophthalmic Research Institute Company

Ryoji Yamamoto

Kinji Iizuka

Hiromu Harada

Tetsuhide Kamijo

Yukiyoshi Ajisawa

Makio Kitazawa

Masuo Akahane

Michihiro Kobayashi

Yukihiko Kinoshita

Yasushi Nakano

Tokihiko Yamamoto

Taihei Shibazaki

Tetsuhide Kamino

Tsutomu Tsukamoto

In preferred embodiments this invention provides a pharmaceutical composition and a method for the treatment of allergic conjunctivitis or allergic rhinitis. The composition is an aqueous solution containing N-(3,4-dimethoxycinnamoyl)anthranilic acid or a pharmaceutically acceptable salt thereof as an active ingredient. The composition additionally contains as essential components polyvinylpyrrolidone, a basic compound and a surface active agent in prescribed quantities, and the composition has a pH of about 6.5-8.5.

Pharmaceutical compositions containing N-(3,4-dimethoxycinnamoyl)

This invention provides novel isatin compounds which are useful as therapeutic agents. The invention isatin compounds and the pharmaceutically acceptable salts thereof exhibit anti-ulcer activities which are applicable for propylaxis and treatment of ulcer diseases in the digestive tract of animals.

Isatin compositions having anti-ulcer activities

The present invention provides an improved method for producing a nuclear substituted cinnamoylanthranilic acid compound. Illustrative of the process is the reaction of 3,4-dimethoxybenzaldehyde with 2-carboxymalonanilic acid in an inert solvent medium in the presence of piperidine to provide an intermediate salt precipitate, and the salt is treated with an acidic reagent to yield N-(3,4-dimethoxycinnamoyl)anthranilic acid product.

Method for the production of nuclear substituted cinnamoylanthranilic

The present invention provides an improved method for producing a nuclear substituted cinnamoylanthranilic acid compound. Illustrative of the process is the reaction of 3-hydroxy-4-methoxybenzaldehyde with 2-carboxymalonanilic acid in an inert solvent medium in the presence of a molar excess of piperidine to provide a high purity intermediate salt precipitate, and the salt is treated with an acidic reagent to yeild N-(3-hydroxy-4-methoxycinnamoyl)anthranilic acid product.

Process for the production of nuclear substituted cinnamoylanthranilic

1,3-Disubstituted imidazoles of the general formula (I): ##STR1## wherein A and B may be the same or different, and each is a straight- or branched-chain alkylene or alkenylene group having 1 to 8 carbon atoms, Y is an acyl group having 2 to 10 carbon atoms, an alkoxycarbonyl group having 2 to 7 carbon atoms or an dialkoxymethyl group having 3 to 13 carbon atoms, Z is a cyano group or an alkoxycarbonyl group having 2 to 7 carbon atoms, X is a halogen atom, n is zero or 1. The said compounds are intermediates for producing the imidazole derivatives of the general formula (V) above which possess strong and specific inhibitory effects on thromboxane synthetase and thus are useful as therapeutical agents for treatment of diseases caused by thromboxane A.sub.2.

1,3-Disubstituted imidazoles

The imidazole derivatives of the general formula: ##STR1## wherein A and B may be the same or different, and each is a straight- or branched-chain alkylene or alkenylene group having 1 to 8 carbon atoms, D is an acyl group having 2 to 10 carbon atoms, an alkoxycarbonyl group having 2 to 7 carbon atoms or a dialkoxymethyl group having 3 to 13 carbon atoms, Q is a cyano group or an alkoxycarbonyl group having 2 to 7 carbon atoms, X is a halogen atom, Z is ##STR2## (wherein E is a hydrogen atom, a halogen atom, an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms, Y is an oxygen atom or a sulfur atom and may be connected with either A or B), n is zero or 1, with the proviso that n is 1 when Y connects with B. These compounds are novel compounds and are useful as intermediates in producing 1-substituted imidazole derivatives which possess strong and specific inhibitory effects on thromboxane synthetase and thus are useful as therapeutically active agents for treatment of diseases caused by thromboxane A.sub.2.

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Matsumoto, Japan

Ryoji Yamamoto