Toyama Chemical Co., Ltd.

Yoichi Taniguchi

Shuntaro Takano

Chosaku Yoshida

Takihiro Inaba

Yukihiko Aikawa

Keiichi Tanaka

Shinji Makino

Tomoya Shimotori

Ichiro Oshio

Junichi Yokotani

Yukie Tada

Eiji Hara

Hitoshi Akitsu

Hiroshi Kato

Minori Yanai

Chiharu Tanabe

Hidehiko Tanaka

Shuzo Anzai

Arihiro Takatori

The invention relates to an N-acyl anthranilic acid derivative or it's salt having collagen production inhibitory action.

N-acyl anthranilic acid derivative or salt thereof

The anthranilic acid derivative or the salt thereof represented by the general formula wherein Rand Rare hydrogen atom, or the like; Ris a phenyl, cycloalkyl or bicyclic heterocyclic group which may be substituted, or the like; Ris a phenyl, cycloalkyl or pyridyl group which may be substituted, or the like; Xis an alkylene or alkenylene group which may be substituted or a bond; Xis the general formula &#x2014;X&#x2014;X&#x2014; or &#x2014;X&#x2014;X&#x2014;, wherein Xis a sulfur atom, an imino group or a bond, or the like; Xmeans an alkylene or alkenylene group which may be substituted or a bond; is useful for a remedy such as rheumatoid arthritis, osteoarthritis and carcinoma, because it shows MMP&#x2014;13 production inhibitory effect.

Anthranilic acid derivative or salt thereof

An anthranilic acid derivative represented by the general formula (X) [wherein Rrepresents hydrogen or a carboxy-protecting group; Rrepresents optionally substituted phenyl, a heterocyclic group, etc.; Rrepresents optionally substituted phenyl, a monocyclic heterocyclic group, etc.; Xrepresents carbonyl, etc.; Xrepresents optionally substituted alkylene group, a bond, etc.; Xrepresents oxygen, a bond, etc.; and Xrepresents a group represented by the general formula &#x2014;X&#x2014;X&#x2014; or &#x2014;X&#x2014;X&#x2014; (wherein Xmeans oxygen, a bond, etc.; and Xmeans optionally substituted alkylene, a bond, etc.)] or a salt of the derivative. The derivative or salt has the inhibitory activity of MMP-13 production and is hence useful as a therapeutic agent for articular rheumatism, osteoarthritis, cancer, etc.

Autoimmune diseases, cell adhesion inhibition and immunomodulation are treated or effected by a method, comprising, treating a patient with a therapeutically effective amount of a 4H-1-benzopyran-4-one compound represented by the following formula or a salt thereof: ##STR1## wherein R.sup.1 is an unsubstituted or halogen-substituted alkyl, alkenyl or aryl group; R.sup.2 is a hydrogen atom or an alkyl or acyl group; R.sup.3 is a hydrogen or halogen atom or a cyano, azido, carboxyl, hydroxyl, formyl or alkoxycarbonyl group or a substituted or unsubstituted alkyl, alkoxy, phenoxy, cycloalkyl, carbamoyl, amino or phenyl group; R.sup.4 is a hydrogen or halogen atom, a nitro, cyano, carboxyl, acyl, hydroxyl or alkoxycarbonyl group, or a substituted or unsubstituted alkyl, alkoxy, alkylthio, phenylthio, alkynyl, alkenyl, sulfamoyl, alkanesulfonyl, alkanesulfonyl, amidino, phenyl or heterocyclic group or a group of the formula ##STR2## where R.sup.6 is a hydrogen atom, a hydroxyl, cyano or alkoxycarbonyl group or a substituted or unsubstituted alkyl, cycloalkyl, phenyl, amino, acyl, carbamoyl, alkanesulfonyl, iminomethyl or amidino group and R.sup.7 is a hydrogen atom or a substituted or unsubstituted alkyl, alkoxy, phenyl, cycloalkyl or heterocyclic group, or R.sup.6 and R.sup.7, when taken together with the nitrogen atom to which the two are bonded, form a 3- to 7-membered, substituted or unsubstituted heterocyclic group; R.sup.5 is a substituted or unsubstituted phenyl, thienyl, furyl or pyridyl group; Z is an oxygen or sulfur atom or an imino group; and the broken line means a single or double bond.

Immunomodulator, cell adhesion inhibitor, and agent for treating, and

Immunomodulator, cell adhesion inhibtor, and agent for treating, and

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Toyama, Japan

Yoichi Taniguchi