Otsuka Pharmaceutical Company, Limited

Minoru Uchida

Kazuyuki Nakagawa

Seiji Morita

Takao Nishi

Masatoshi Chihiro

Kimiaki Oka

Michiaki Tominaga

Hidenori Ogawa

Yoichi Yabuuchi

Kazumi Kondo

Tomoichi Shinohara

Muneaki Kurimura

Keizo Kan

Kenji Otsubo

Toyoki Mori

Yoshihisa Tanada

Makoto Komatsu

Katsuya Yamasaki

Takefumi Shimizu

Hiroaki Oka

Kazuyukip Nakagawa

Kamuyuki Nakagawa

Makoto Komastu

Benzazepine derivatives with vasopressin agonistic activity

Quinoline derivative and antiulcer agent containing said quinoline

A hydroquinoline compound of the formula (1): ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, A, l, m and n are as defined or its pharmaceutically acceptable salt, composition containing the compound and processes for preparing same are disclosed. The compound is useful as an antiulcer agent.

Benzimidazolyl-sulfinyl-tetrahydroquinolines

Novel tetrahydroquinoline derivatives and salts thereof and novel imidazopyridine derivatives and salts thereof, both having excellent anti-peptic ulcer activities, and are useful as treating agents for peptic ulcers such as gastric ulcer, duodenum ulcer and the like.

Imidazopyridyl-alkylthio-pyridines and anti-peptic ulcer compositions

Tetrazole derivatives of the formula: ##STR1## wherein R.sup.1 is an optional defined substituent; A is sulfur or a lower alkylene-thio, l is 0 or 1; B is a lower alkylene; R.sup.2 is hydroxy, a lower alkoxy, or a group: ##STR2## wherein R.sup.3 and R.sup.4 are optional defined substituents, or the R.sup.3 or R.sup.4 may combine together with the nitrogen atom to which they are joined to form a defined heterocyclic group, and a pharmaceutically acceptable salt thereof, which have prophylactic or therapeutic activities against peptic and/or duodenal ulcers and also anti-inflammatory activity and are useful as an anti-ulcer or anti-inflammatory drug; processes for the preparation of the tetrazole derivatives; and pharmaceutical compositon containing said tetrazole derivatives.

Tetrazole derivatives, having a further unsaturated heterocyclic ring

Benzimidazolyl-thio-tetrahydroquinolines and anti-peptic ulcer

Novel oxindole derivative and salt thereof represented by the general formula, ##STR1## wherein R.sup.1 is a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group or a phenyl-lower alkyl group; R.sup.2 is a hydrogen atom or a lower alkyl group; R.sup.3 is a hydrogen atom, a cycloalkylcarbonyl group, a benzoyl group which may have 1 to 3 substituents selected from the group consisting of a halogen atom, a lower alkyl group and a lower alkoxy group on the phenyl ring, or a phenyl-lower alkanoyl group which may have halogen atoms as the substituents on the phenyl ring; provided that when R.sup.4 is a hydrogen atom, then R.sup.3 should be neither a hydrogen atom nor a lower alkyl group. The novel oxindole derivative and salt thereof possesses anti-peptic ulcer effects and are useful as anti-peptic ulcer agents.

2-amido 3(oxindol-3-yl)propionic acids having antiulcer activity

Tetrazole derivatives of the formula: ##STR1## wherein R.sup.1 is an optional defined substituent; A is sulfur or a lower alkylene-thio, l is 0 or 1; B is a lower alkylene; R.sup.2 is hydroxy, a lower alkoxy, or a group: ##STR2## wherein R.sup.3 and R.sup.4 are optional defined substituents, or the R.sup.3 and R.sup.4 may combine together with the nitrogen atom to which they are joined to form a defined heterocyclic group, and a pharmaceutically acceptable salt thereof, which have prophylactic or therapeutic activities against peptic and/or duodenal ulcers and also anti-inflammatory activity and are useful as an anti-ulcer or anti-inflammatory drug; processes for the preparation of the tetrazole derivatives; and pharmaceutical composition containing said tetrazole derivatives.

Tetrazole derivatives, anti-ulcer composition containing the same and

Disclosed are carbostyril derivatives and their salts of the formulas ##STR1## The compounds have anti-peptic ulcer effects, and are useful as a treating agent for curing peptic ulcers in the digestive system, such as ulcers in the stomach and in the duodenum. The compounds particularly have prophylaxis and curing effects for treating chronic ulcers, for example experimental acetic acid-induced ulcers and cautery ulcers, with both low toxicity and few side-effects. Also disclosed are processes for preparing the compounds and for preparing pharmaceutical compositions containing them.

Carbostyril derivatives

Tetrazole derivatives of the formula: ##STR1## wherein R.sup.1 is an optional defined substituent; A is sulfur or a lower alkylene-thio; l is 0 or 1; B is a lower alkylene; R.sup.2 is hydroxy, a lower alkoxy, or a group: ##STR2## wherein R.sup.3 and R.sup.4 are optional defined substituents, or the R.sup.3 and R.sup.4 may combine together with the nitrogen atom to which they are joined to form a defined heterocyclic group, and a pharmaceutically acceptable salt thereof, which have prophylactic or therapeutic activities against peptic and/or duodenal ulcers and also anti-inflammatory activity and are useful as an anti-ulcer or anti-inflammatory drug; processes for the preparation of the tetrazole derivatives; and pharmaceutical composition containing said tetrazole derivatives.

Tetrazole derivatives of the formula: ##STR1## wherein R.sup.1 is a lower alkykl, phenyl or a group of the formula: --S(O).sub.l --A--(X).sub.m --R.sup.3, and R.sup.2 is hydrogen, a lower alkyl, phenyl or a cycloalkyl when R.sup.1 is the group --S(O).sub.l --A--(X).sub.m --R.sup.3, or R.sup.2 is a group of the formula: --B--CO--R.sup.4 when R.sup.1 is a lower alkyl or phenyl and a pharmaceutically acceptable salt thereof, which have prophylactic or therapeutic activities against peptic and/or duodenal ulcers and are useful as an anti-ulcer drug; processes for the preparation of the tetrazole derivatives; and pharmaceutical composition containing said tetrazole derivatives.

Tetrazole derivatives, and anti-ulcer composition containing the same

2-oxyindole derivatives represented by the following general formula: ##STR1## where R.sub.1 is selected from the group consisting of hydrogen, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, benzyl and phenethyl; A is --CH.dbd.CH-- or ##STR2## wherein R.sub.2 or R.sub.3 may be the same or different and are selected from the group consisting of hydrogen and C.sub.1-4 alkyl; R.sub.6 and R.sub.7 may be the same or different and are selected from the group consisting of hydrogen, C.sub.1-4 alkyl, benzyl, phenethyl and together with the nitrogen atom, a heterocyclic group selected from the group consisting of a piperidino, morpholino, piperazino or thiazolino group; and m and n each are zero or a positive integer with m+n being no more than 11. The 2-oxyindole derivatives have excellent effects on the inhibition of platelet aggregation.

Platelet aggregation inhibiting 2-oxyindoles, their compositions and

2-Oxyindole derivatives represented by the following general formula: ##STR1## where R.sub.1 is selected from the group consisting of hydrogen, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, benzyl and phenethyl; A is --CH.dbd.CH-- or ##STR2## wherein R.sub.2 or R.sub.3 may be the same or different and are selected from the group consisting of hydrogen and C.sub.1-4 alkyl; R.sub.4 is --OR.sub.5, wherein R.sub.5 is selected from the group consisting of hydrogen, C.sub.1-8 alkyl, cyclohexyl, benzyl and phenethyl, or ##STR3## wherein R.sub.6 and R.sub.7 may be the same or different and are selected from the group consisting of hydrogen, C.sub.1-4 alkyl, benzyl, phenethyl and together with the nitrogen atom, a heterocyclic group selected from the group consisting of a piperidino, morpholino, piperazino or thiazolino group; and m and n each are zero or a positive integer with m+n being no more than 11. The 2-oxyindole derivatives have excellent effects on the inhibition of platelet aggregation.

Novel (3'-alkylamino-2'-hydroxy)propoxy-3,4-dihydrocarbostyril derivatives having .beta.-adrenergic nerves blocking activity and hypotensive activity and useful as a remedy for angina pectoris, irregular pulse and hypertension, etc., represented by the formula, ##STR1## wherein R.sub.1 is hydrogen, C.sub.1 -C.sub.4 alkyl or aralkyl and R.sub.2 is C.sub.1 -C.sub.4 alkyl, are prepared by reacting a 3,4-dihydrocarbostyril derivative represented by the formula, ##STR2## wherein R.sub.1 is C.sub.1 -C.sub.4 alkyl or aralkyl, with an epihalogenohydrin represented by the formula, ##STR3## wherein X is halogen, reacting the resulting product with an alkylamine represented by the formula,

3,4-Dihydrocarbostyril derivatives

Novel benzcycloamide derivatives represented by the general formula, ##STR1## wherein R.sub.1 is hydrogen, C.sub.1-4 alkyl, C.sub.2-4 alkenyl or aralkyl; B is --CH.sub.2 --, --CH.sub.2 --CH.sub.2 -- or --CH.dbd.CH--; A is ##STR2## (wherein R.sub.2 and R.sub.3 may be the same or different and are respectively hydrogen or C.sub.1-4 alkyl) or --CH.dbd.CH--; R.sub.4 is --OR.sub.5 (wherein R.sub.5 is hydrogen, C.sub.1-8 alkyl, cycloalkyl or aralkyl) or ##STR3## (wherein R.sub.6 and R.sub.7 may be the same or different and are respectively hydrogen, C.sub.1-4 alkyl or aralkyl or may form together with the nitrogen atom a 5- or 6-membered heterocyclic group which may further contain a nitrogen, oxygen or sulfur atom); and m and n each are zero or a positive integer and m + n is no more than 11. The benzcycloamide derivatives represented by the above-mentioned general formula (I) have excellent effects of inhibiting platelet aggregation and are useful as preventives for thrombosis and embolism.

Growing community of inventors

Komatsushima, Japan

Minoru Uchida