Takeda Chemical Industries, Inc.

Yoshitaka Maki

Akira Nohara

Shinji Terao

Mitsuru Shiraishi

Masazumi Watanabe

Yoshiyasu Furukawa

Quinone derivatives of the general formula: ##STR1## (wherein R.sup.1 and R.sup.2 are the same or different, and independently are a hydrogen atom or a methyl or methoxy group, or R.sup.1 and R.sup.2 combine with each other to represent --CH.dbd.CH--CH.dbd.CH--; R.sup.3 is a hydrogen atom or a methyl group; R.sup.4 is an aliphatic, aromatic or heterocyclic group which may be substituted; R.sup.5 is a methyl or methoxy group, a hydroxymethyl group which may be substituted or a carboxyl group which may be esterified or amidated; Z is a group represented by --C.tbd.C--, --CH.dbd.CH--, ##STR2## n is an integer of 0 to 10; m is an integer of 0 to 3; k is an integer of 0 to 5, provided, however, that in the case of m being 2 or 3, Z and k can vary arbitrarily within the bracketed repeating units) are novel compounds, possess metabolism ameliorating action for polyunsaturate fatty acids, particularly production inhibitory activity of lipid peroxides (antioxidant activity), thromboxane A.sub.2 receptor antagonism, or production inhibitory activity of 5-lipoxygenase metabolites in mammals, and of use as drugs, such as antiasthmatic, antiallergic agent and cerebral-circulatory metabolism ameliorating agent.

Quinone derivatives, their production and use

Quinone derivatives of the general formula: ##STR1## (wherein R.sup.1 and R.sup.2 are the same or different, and independently are a hydrogen atom or a methyl or methoxy group, or R.sup.1 and R.sup.2 combine with each other to represent --CH.dbd.CH--CH.dbd.CH--R.sup.3 is a hydrogen atom or a methyl group; R.sup.4 is an aliphatic, aromatic or heterocyclic group which may be substituted; R.sup.5 is a methyl or methoxy group, a hydroxymethyl group which may be substituted or a carboxyl group which may be esterified or amidated; Z is a group represented by --C.dbd.C--, --CH.dbd.CH--, ##STR2## n is an integer of 0 to 10; m is an integer of 0 to 3; k is an integer of 0 to 5, provided, however, that in the case of m being 2 or 3, Z and k can vary arbitrarily within the bracketed repeating units) are novel compounds, possess metabolism ameliorating action for polyunsaturated fatty acids, particularly production inhibitory activity of lipid peroxides (antioxidant activity), thromboxane A.sub.2 receptor antagonism, or production inhibitory activity of 5-lipoxygenase metabolites in mammals, and of use as drugs, such as antiasthmatic, antiallergic agent and cerebral-circulatory metabolism ameliorating agent.

A compound of the formula ##STR1## wherein R is a lower alkyl group, R.sup.0 is hydrogen or an acyl group, R.sup.1 and R.sup.2 are lower alkyl groups which may optionally be substituted or wherein R.sup.1 and R.sup.2 are combined to form a butadienylene group which may optionally be substituted, R.sup.3 and R.sup.4 are hydrogen or alkyl groups which may optionally be substituted or wherein R.sup.3 and R.sup.4 are combined to form a polymethylene group, and R.sup.5 is a lower alkyl, aromatic or heterocyclic group which may optionally be substituted or a pharmaceutically acceptable salt thereof, exerts cardiovascular system improving action and antiallergic action and can be used as pharmaceutics, e.g. antithromotics, antiallergic agents etc.

Coumaran derivatives and their pharmaceutical use

The compound of the formula ##STR1## wherein R.sup.1 is hydrogen, methoxy or trifluormethyl, R.sup.2 and R.sup.3 are the same or different and are each hydrogen or methyl, R.sup.4 is a fluorinated lower alkyl having 2 to 5 carbon atoms and 1 to 11 fluorine atoms and X.sup.- is a pharmaceutically acceptable anion, respectively, possesses both strong antisecretory activity and gastric mucosal protective activity, which is produced by reacting a pyridine derivative of the formula ##STR2## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 have the same meaning as defined above, with an acid.

Sulfenamide derivatives and their production

The compound of the formula ##STR1## wherein R.sup.1 is hydrogen, fluorine, methoxy or trifluoromethyl, R.sup.2 is a C.sub.1-8 alkyl, R.sup.3 is a C.sub.1-8 alkyl which may be fluorinated, and n is 0 or 1, or a pharmacologically acceptable salt thereof is useful for prevention and treatment of digestive ulcers (e.g. gastric ulcer, duodenal ulcer) and gastritis.

Pyridine derivatives, and use as anti-ulcer agents

The compound of the formula ##STR1## wherein R.sup.1 is hydrogen, fluorine, methoxy or trifluoromethyl, R.sup.2 is hydrogen or methyl, R.sup.3 is a C.sub.3-8 straight-chain or branched alkyl, and n denotes 0 or 1, or their pharmacologically acceptable salts is novel and useful for prophylaxis and therapy of digestive ulcers (e.g. gastric ulcer, duodenal ulcer) and gastritis.

Pyridyl methylsulfinyl benzimidazole derivatives

A benzoic acid derivative of the formula: ##STR1## wherein R.sup.1 stands for a lower alkyl group, R.sup.2 stands for an optionally protected carboxyl group and X stands for a halogen or a salt thereof, has excellent antiasthmatic and antiinflammatory activities and therefore is useful as an antiasthmatic or antiinflammatory agent for a mammalian animal.

Benzoic acid derivatives and their production

The compound of the formula ##STR1## wherein R.sup.1 is hydrogen, methoxy or trifluoromethyl, R.sup.2 and R.sup.3 are independently hydrogen or methyl, R.sup.4 is a C.sub.2-5 fluorinated alkyl and n denotes 0 or 1, or a pharmacologically acceptable salt thereof is novel, and useful for prophylaxis and therapy of digestive ulcers (e.g. gastric ulcer, duodenal ulcer) and gastritis.

2-(2-pyridylmethylthio (sulfinyl)) benzimidazoles

A diphenoxypropane derivative of the formula: ##STR1## wherein X is a halogen atom, Y is a hydrogen atom or a hydroxy group and Z is a tetrazolyl or carboxy group, has excellent antiasthmatic and antiinflammatory activities, and therefore the diphenoxypropane derivatives are useful as antiasthmatic or antiiflammatory agents.

Diphenoxypropane derivatives, its production and use 5-tetrazolyl

2-[2-pyridylmethylthio-(sulfinyl)]benzimidazoles

Novel compounds of the formula: ##STR1## wherein R.sup.1 stands for an optionally substituted alkyl group, alkenyl group, aryl group, aralkyl group, cycloalkyl group, heterocyclic group having carbon as the bonding hand or amino group, R.sup.2 stands for a pyridyl group which may be substituted with alkyl group, and R.sup.3 stands for an optionally substituted aryl group or salts thereof, have analgesic, anti-piretic, anti-inflammatory and anti-ulcer actions, and can be administered to mammals for the therapy of pain, inflammatory diseases, rheumatic chronic diseases.

5-pyridyl-1,3-thiazole derivatives

Novel 3-aminopyrazolo[3,4-d]pyrimidine derivatives represented by the general formula (I) ##STR1## wherein R.sub.1 and R.sub.2 each represents an aliphatic hydrocarbon group; R.sub.3 and R.sub.4 each represents hydrogen, alkyl or acyl; R.sub.5 is alkyl, alkoxycarbonyl or formyl; and the dotted line designates the presence of two double bonds on the pyrazole ring, to which R.sub.5 is linked at either the 1- or 2-position and their salts, are useful for antiinflammatory, analgesic and antipyretic agents.

3-aminopyrazolo[3,4-d]pyrimidine derivatives and production thereof

A diphenoxypropane derivative of the formula: ##STR1## wherein X is a halogen atom, Y is a hydrogen atom or a hydroxy group and Z is a tetrazolyl or carboxy group, has excellent antiasthmatic and antiinflammatory activities, and therefore the diphenoxypropane derivatives are useful as antiasthmatic or antiinflammatory agents.

Diphenoxypropane derivatives and compositions of antiasthmatic and

New quinone compounds of the formula: ##STR1## wherein R is methyl or methoxy and

Quinone compounds, their production and use

New quinone compounds of the formula: ##STR1## wherein R.sup.1 is methyl or methoxy, or the two R.sup.1 groups jointly represent --CH.dbd.CH--CH.dbd.CH--; X is --CH.dbd.CH-- or --C.dbd.C--; Y.sup.1 is hydrogen, hydroxyl, carboxyl, cyano, acyloxy or --COZ in which Z is amino which may be substituted; m is zero or an integer of 1 to 3; n is zero or an integer of 1 to 10; n' is an integer of 1 to 5; k is an integer of 1 to 3; and when k is 2 or 3, n' is optionally variable within the range of 1 to 5 in each occurrence of the --X--(CH.sub.2).sub.n' group; and their hydroquinone forms and salts, have useful physiological activities such as antiasthmatic, antiallergic and bloodpressure decreasing activities.

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Kyoto, Japan

Yoshitaka Maki