Patents Assigned to Otsuka Pharmaceutical Company Limited
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Patent number: 5401754Abstract: A pharmaceutical preparation comprising at least one compound selected from the group consisting of carbostyril derivatives having the general formula: ##STR1## wherein R.sup.1 is hydrogen or a lower alkyl group optionally having hydroxy group as a substituent; R.sup.2 is a phenyl(lower alkyl) group optionally having 1 to 3 substituents selected from the group consisting of a lower alkoxy group and a halogen atom on the phenyl ring, pyridyl(lower alkyl) group, or a group of the formula --A--NR.sup.3 R.sup.4 (wherein A is a lower alkylene group, R.sup.3 and R.sup.4 are the same or different and represent a lower alkyl group or phenyl group), and a salt thereof, which is useful as an agent for treating thrombosis, more particularly, as an agent for inhibiting platelet aggregation and as an agent for platelet aggregate dissociation.Type: GrantFiled: March 11, 1994Date of Patent: March 28, 1995Assignee: Otsuka Pharmaceutical Company, LimitedInventors: Takafumi Fujioka, Shuji Teramoto, Michiaki Tominaga, Yoichi Yabuuchi
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Patent number: 5385914Abstract: Method for prophylaxis and treatment of heart diseases using a carbostyril derivative-of formula: ##STR1## wherein R.sup.1 is H or CN, and R.sup.2 and R.sup.3 are each H, alkyl optionally substituted by OH, cycloalkyl, alkenyl, phenyl, phenylalkyl having optionally substituents of alkoxyalkoxy, halogen, alkoxy, NO.sub.2, alkyl, CN, alkylthio or alkylsulfinyl on phenyl ring and having optionally OH-substituent on alkyl moiety, phenylsulfonylalkyl having optionally alkoxy substituent on phenyl ring, phenylthioalkyl, phenylsulfinylalkyl having optionally substituents of halogen or alkoxy on phenyl ring, phenoxyalkyl having optionally substituents of halogen or alkoxy on phenyl ring, pyridylalkyl having optionally substituents of halogen or alkoxy on pyridine ring, thienylalkyl, benzoylalkyl, anilinothiocarbonyl, benzoyl, pyridyl, phenylalkenyl, or group of --A--NR.sup.4 R.sup.5 (R.sup.4 and R.sup.Type: GrantFiled: November 12, 1993Date of Patent: January 31, 1995Assignee: Otsuka Pharmaceutical Company, LimitedInventors: Takafumi Fujioka, Shuji Teramoto, Michiaki Tominaga, Yoichi Yabuuchi
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Patent number: 5290934Abstract: Novel 4-oxoquinoline-3-carboxylic acid compounds of the formula: ##STR1## wherein R.sup.1 is cyclopropyl which may have 1 to 3 substituents of alkyl and halogen; phenyl which may be substituted by 1 to 3 substituents of alkoxy, halogen and OH; alkyl which may be substituted by halogen, alkanoyloxy or OH; alkenyl; or thienyl, R.sup.2 is 5- to 9-membered saturated or unsaturated heterocyclic ring which may be substituted, R.sup.3 is alkyl, R is H or alkyl, and X is halogen, and pharmaceutically acceptable salts thereof, said compounds having excellent antimicrobial activity and hence being useful as an antimicrobial agent, and a pharmaceutical composition containing said compound as an active ingredient.Type: GrantFiled: June 4, 1991Date of Patent: March 1, 1994Assignee: Otsuka Pharmaceutical Company, LimitedInventors: Hiraki Ueda, Hisashi Miyamoto, Hiroshi Yamashita, Hitoshi Tone
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Patent number: 5198448Abstract: Method for prophylaxis and treatment of heart diseases using a carbostyril derivative of formula: ##STR1## wherein R.sup.1 is H or CN, and R.sup.2 and R.sup.3 are each H, alkyl optionally substituted by OH, cycloalkyl, alkenyl, phenyl, phenylalkyl having optionally substituents of alkoxyalkoxy, halogen, alkoxy, NO.sub.2, alkyl, CN, alkylthio or alkylsulfinyl on phenyl ring and having optionally OH-substituent on alkyl moiety, phenylsulfonylalkyl having optionally alkoxy substituent on phenyl ring, phenylthioalkyl, phenylsulfinylalkyl having optionally substituents of halogen or alkoxy on phenyl ring, phenoxyalkyl having optionally substituents of halogen or alkoxy on phenyl ring, pyridylalkyl having optionally substituents of halogen or alkoxy on pyridine ring, thienylalkyl, benzoylalkyl, anilinothiocarbonyl, benzoyl, pyridyl, phenylalkenyl, or group of --A-NR.sup.4 R.sup.5 (R.sup.4 and R.sup.Type: GrantFiled: July 24, 1991Date of Patent: March 30, 1993Assignee: Otsuka Pharmaceutical Company, LimitedInventors: Takafumi Fujioka, Shuji Teramoto, Michiaki Tominaga, Yoichi Yabuuchi
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Patent number: 5145865Abstract: Phenylcarboxylic acid derivatives having a hetero ring in the substituent of the formula: ##STR1## wherein R.sup.1 is halogen, alkyl, cycloalkyl, hydroxy, alkoxy, phenoxy which has a substituent selected from halogen and alkyl, carboxyl, alkylsulfonyloxy, phenylsulfonyloxy optionally substituted by halogen, alkylsulfonyloxyalkoxy, amino, alkanoylamino, benzoylamino, alkenyloxy, phenylalkoxyalkoxy, hydroxyalkoxy, phenylalkoxy having optionally 1 to 3 substituents selected from halogen, alkyl and alkoxy, halogenoalkyl, cycloalkyloxy optionally substituted by hydroxy, alkoxy substituted by cycloalkyl having optionally hydroxy substituent, imidazolylalkyl or imidazolylalkoxy; k is 0 or 1 to 3; or (R.sup.1).sub.k is alkylenedioxy; A is alkylene or alkylenoxy; l is 0 or 1; B is methylene or carbonyl; m is 0 or 1; D is alkylene; E is alkylene or alkenylene; n is 0 or 1; and R.sup.Type: GrantFiled: April 19, 1990Date of Patent: September 8, 1992Assignee: Otsuka Pharmaceutical Company, LimitedInventors: Setsuro Fujii, deceased, by Shinichiro Fujii, administrator, by Kaoruko Takada, administrator, Hiroyuki Kawamura, Shinichi Watanabe
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Patent number: 5053514Abstract: Method for prophylaxis and treatment of heart diseases using a carbostyril derivative of formula: ##STR1## wherein R.sup.1 is H or CN, and R.sup.2 and R.sup.3 are each H, alkyl optionally substituted by OH, cyclocalkyl, alkenyl, phenyl, phenylalkyl having optionally substituents of alkoxyalkoxy, halogen, alkoxy, NO.sub.2, alkyl, CN, alkylthio or alkylsulfinyl on phenyl ring and having optionally OH-substituent on alkyl moiety, phenylsulfonyl having optionally alkoxy substituent on phenyl ring, phenylthioalkyl, phenylsulfinylalkyl having optionally substituents of halogen or alkoxy on phenyl ring, phenoxyalkyl having optionally substituents of halogen or alkoxy on phenyl ring, pyridylalkyl having optionally substituents of halogen or alkoxy on pyridine ring, thienylalkyl, benzoyalkyl, anilinothiocarbonyl, benzoyl, pyridyl, phenylalkenyl, or group of --A--NR.sup.4 R.sup.5 (R.sup.4 and R.sup.Type: GrantFiled: August 9, 1989Date of Patent: October 1, 1991Assignee: Otsuka Pharmaceutical Company, LimitedInventors: Takafumi Fujioka, Shuji Teramoto, Michiaki Tominaga, Yoichi Yabuuchi
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Patent number: 4999378Abstract: Phenylcarboxylic acid derivatives having the formula: ##STR1## wherein R.sup.1 and R.sup.2 are each H, halogen, alkyl, haloalkyl, alkanoyl, cycloalkyl, nitro, amino, --O--D--R.sup.5 (D is alkylene, R.sup.5 is H, amino, morpholino, carboxyl, phthalimido, phenyl, epoxy), substituted or unsubstituted phenoxy, substituted or unsubstituted phenylalkylamino, carboxylalkenyl, or both form alkylenedioxy; R.sup.3 is H, --E--R.sup.6 (E is alkylene, R.sup.6 is H, carboxyl, cyano, OH, phenylalkoxy, or halogen-substituted phenyl, or phenylcarbamoyl), --CO--G--R.sup.7 (G is alkylene, R.sup.7 is H, substituted or unsubstituted phenylcarbamoyl), substituted or unsubstituted benzoyl, alkenyl, carbamoyl, phenyl, or halophenyl; R.sup.4 is H or alkyl; A is alkylene, alkylene condensed with cycloalkyl ring, or alkenylene; B is alkylene or alkenylene; l is 0 or 1.Type: GrantFiled: June 20, 1989Date of Patent: March 12, 1991Assignee: Otsuka Pharmaceutical Company, LimitedInventors: Setsuro Fujii, Hiroyuki Kawamura, Shinichi Watanabe
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Patent number: 4971970Abstract: Novel 3-formyl-4-oxoquinoline compounds of the formula: ##STR1## wherein R.sup.1 is hydrogen atom or a lower alkanoyl, R.sup.2 is hydrogen atom or a lower alkyl, R.sup.3 is a lower alkyl, and X is halogen, and pharmaceutically acceptable salts thereof, said compounds having excellent antimicrobial activity and hence being useful as an antimicrobial agent, and a pharmaceutical composition containing said compound as an active ingredient.Type: GrantFiled: October 20, 1989Date of Patent: November 20, 1990Assignee: Otsuka Pharmaceutical Company, LimitedInventors: Hisashi Miyamoto, Hiroshi Yamashita, Michiaki Tominaga, Yoichi Yabuuchi
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Patent number: 4880806Abstract: Novel 4-oxoquinoline-3-carboxylic acid compounds of the formula: ##STR1## wherein R.sup.2 is a heterocyclic group: ##STR2## in which R.sup.A is H, C.sub.1 -C.sub.6 alkyl or phenyl (C.sub.1 -C.sub.6) alkyl, R.sup.B is 2-oxo-1,3-dioxolenemethyl substituted by C.sub.1 -C.sub.6 alkyl, or C.sub.3 -C.sub.8 cycloalkyl, R.sup.C is H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxycarbonyl, or phenyl(C.sub.1 -C.sub.6)alkyl, R.sup.D is H or C.sub.1 -C.sub.6 alkyl, R.sup.G is C.sub.1 -C.sub.6 alkyl, and R.sup.H is C.sub.1 -C.sub.6 alkyl, phenyl(C.sub.1 -C.sub.6)alkyl, or C.sub.1 C.sub.6 alkanoyl, and R.sup.3 is C.sub.1 -C.sub.6 alkyl, or R.sup.3 is C.sub.1 -C.sub.6 alkyl having 1 to 3 substituents selected from OH, C.sub.1 -C.sub.6 alkoxy and halogen when R.sup.2 is ##STR3## or a salt thereof, said compounds having excellent antimicrobial activity and being useful as an antimicrobial agent, and a pharmaceutical composition containing said compound as an active ingredient.Type: GrantFiled: July 23, 1987Date of Patent: November 14, 1989Assignee: Otsuka Pharmaceutical Company, LimitedInventors: Hiraki Ueda, Hisashi Miyamoto, Shinji Aki, Tatsuya Otsuka
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Patent number: 4874764Abstract: Novel 4-oxoquinoline-3-carboxylic acid compounds of the formula: ##STR1## wherein R.sup.3 is C.sub.1 -C.sub.6 alkyl and R.sup.F is C.sub.1 -C.sub.6 alkyl, and a pharmaceutically acceptable salts thereof, said compounds having excellent antimicrobial activity and hence being useful as an antimicrobial agent, and a pharmaceutical composition containing said compound as an active ingredient.Type: GrantFiled: June 18, 1987Date of Patent: October 17, 1989Assignee: Otsuka Pharmaceutical Company, LimitedInventors: Hiraki Ueda, Hisashi Miyamoto, Shinji Aki, Tatsuya Otsuka
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Patent number: 4855292Abstract: Novel 4-oxoquinoline-3-carboxylic acid compounds of the formula: ##STR1## wherein R.sup.2 is 1-pyrrolidinyl which may have 1 to 2 substituents selected from the group consisting of (i) C.sub.1 -C.sub.6 alkyl, (ii) amino-(C.sub.1 -C.sub.6)alkyl, said amino being optionally substituted by 1 or 2 substituents selected from C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkanoyl, and C.sub.1 -C.sub.6 alkoxycarbonyl, (iii) amino which may be substituted by 1 or 2 substituents selected from C.sub.1 -C.sub.6 alkyl, phenyl(C.sub.1 -C.sub.6)alkyl, C.sub.1 -C.sub.6 alkoxycarbonyl, and C.sub.1 -C.sub.6 alkanoyl, and (iv) 2-oxo-1,3-dioxolenemethylamino which is substituted by C.sub.1 -C.sub.6 alkyl; or 1-piperidinyl which may have 1 to 3 substituents selected from oxo, hydroxy, halogen and C.sub.1 -C.sub.6 alkyl, and R.sup.3 is C.sub.1 -C.sub.Type: GrantFiled: July 23, 1987Date of Patent: August 8, 1989Assignee: Otsuka Pharmaceutical Company, LimitedInventors: Hiraki Ueda, Hisashi Miyamoto, Shinji Aki, Tatsuya Otsuka
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Patent number: 4824834Abstract: Pyrazolotriazine compounds of the formula: ##STR1## wherein R.sup.1 is OH or alkanoyloxy; R.sup.2 is H, OH, or SH; R.sup.3 is (1) unsaturated N- or S-containing heterocyclic group optionally having 1-2 substituents of halogen, nitro or phenylthio, (2) naphthyl, (3) phenyl optionally having 1-3 substituents of (i) alkyl, (ii) phenyl, (iii) alkoxycarbonyl, (iv) cyano, (v) nitro, (vi) alkoxy, (vii) phenylalkoxy (viii) phenylthio-alkyl, (ix) phenoxy, (x) ##STR2## R is alkyl, halo-substituted alkyl, phenyl optionally having 1-3 substituents, or pyridyl, and l is 0, 1 or 2, (xi) halogen, (xii) phenylalkyl, (xiii) carboxy, (xiv) alkanoyl, (xv) benzoyl optionally having 1-3 substituents, (xvi) amino, (xvii) OH, (xviii) alkanoyloxy, (xix) ##STR3## or (xx) ##STR4## (A is alkylene), said compounds having a xanthine oxidase inhibitory activity and are useful for the prophylaxis and treatment of gout.Type: GrantFiled: October 8, 1987Date of Patent: April 25, 1989Assignee: Otsuka Pharmaceutical Company, LimitedInventors: Setsuro Fujii, Hiroyuki Kawamura, Hiroshi Kiyokawa, Satoshi Yamada
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Patent number: 4786649Abstract: Novel 1-thienyl-4-oxoquinoline-3-carboxylic acid compounds of the formula ##STR1## wherein R.sup.1 is an amino (lower) alkyl, R.sup.2 is thienyl, and X is a halogen atom, and a pharmaceutically acceptable salt thereof, said compounds having excellent antimicrobial activity and hence being useful as an antimicrobial agent, and a pharmaceutical composition comprising as an active ingredient said 1-thienyl-4-oxoquinoline-3-carboxylic acid compounds or a pharmaceutically acceptable salt thereof in admixture with a pharmaceutically acceptable diluent or carrier.Type: GrantFiled: November 13, 1986Date of Patent: November 22, 1988Assignee: Otsuka Pharmaceutical Company LimitedInventors: Hiraki Ueda, Hisashi Miyamoto
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Patent number: 4766120Abstract: 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.Type: GrantFiled: May 30, 1986Date of Patent: August 23, 1988Assignee: Otsuka Pharmaceutical Company, LimitedInventors: Minoru Uchida, Takao Nishi, Kazuyuki Nakagawa
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Patent number: 4755513Abstract: Novel 1-substituted phenyl-4-oxoquinoline-3-carboxylic acid compounds of the formula: ##STR1## wherein R.sup.1 is hydrogen atom or an alkyl having 1 to 2 carbon atoms, R.sup.2 is hydrogen atom or fluorine atom, and R.sup.3 is hydroxy, fluorine atom or an alkanoyloxy having 1 to 6 carbon atoms, and a pharmaceutically acceptable salt thereof, said compounds having excellent antimicrobial activity and hence being useful as an antimicrobial agent, and a pharmaceutical composition comprising as an active ingredient said 1-substituted phenyl-4-oxoquinoline-3-carboxylic acid compounds or a pharmaceutically acceptable salt thereof in admixture with a pharmaceutically acceptable diluent or carrier.Type: GrantFiled: August 16, 1985Date of Patent: July 5, 1988Assignee: Otsuka Pharmaceutical Company, LimitedInventors: Hitoshi Tone, Hisashi Miyamoto, Hiraki Ueda, Kazuyuki Nakagawa
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Patent number: 4684648Abstract: Novel 1-substituted phenyl-4-oxoquinoline-3-carboxylic acid compounds of the formula: ##STR1## wherein R is hydrogen atom or fluorine atom, R.degree. is hydroxy, fluorine atom or an alkanoyloxy having 1 to 6 carbon atoms, and X.sup.1 is hydrogen atom or fluorine atom, and a pharmaceutically acceptable salt thereof, said compounds having excellent antimicrobial activity and hence being useful as an antimicrobial agent, and a pharmaceutical composition comprising as an active ingredient said 1-substituted phenyl-4-oxoquinoline-3-carboxylic acid compounds or a pharmaceutically acceptable salt thereof in admixture with a pharmaceutically acceptable diluent or carrier.Type: GrantFiled: August 28, 1985Date of Patent: August 4, 1987Assignee: Otsuka Pharmaceutical Company LimitedInventors: Hitoshi Tone, Hisashi Miyamoto, Hiraki Ueda, Kazuyuki Nakagawa
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Patent number: 4593035Abstract: Novel carbostyril derivatives of the formula: ##STR1## wherein R.sup.1 is hydrogen atom or a lower alkyl group, R.sup.2 is a lower alkyl group or a group of the formula: ##STR2## R.sup.3 is a lower alkylthio group, a lower alkyl group, a lower alkoxy group, phenoxy group, a phenyl(lower)alkoxy group, a lower alkenyloxy group, a phenyl group which may have a substituent selected from a lower alkoxy and a lower alkylenedioxy group on the phenyl ring, or a group of the formula: --NR.sup.4 R.sup.5 (R.sup.4 and R.sup.5 are the same or different and are each hydrogen atom or a lower alkyl group), and X is oxygen atom or sulfur atom, provided that when R.sup.1 is hydrogen atom and R.sup.2 is the group of the formula: ##STR3## X is not oxygen atom and R.sup.Type: GrantFiled: December 10, 1984Date of Patent: June 3, 1986Assignee: Otsuka Pharmaceutical Company LimitedInventors: Michiaki Tominaga, Hidenori Ogawa, Takafumi Fujioka, Yung-hsiung Yang, Kazuyuki Nakagawa
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Patent number: 4544747Abstract: A quinoline carboxylic acid derivative of the general formula ##STR1## [wherein R.sup.1 and R.sup.2 are a lower alkyl group, respectively, and R.sup.3 is a halogen atom or 1-piperazinyl group] and its salt are of value as an antimicrobial agent for medical treatment and agricultural and horticultural uses.Type: GrantFiled: April 27, 1984Date of Patent: October 1, 1985Assignee: Otsuka Pharmaceutical Company, LimitedInventors: Hiroshi Ishikawa, Fujio Tabasa, Kazuyuki Nakagawa
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Patent number: 4540703Abstract: 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.Type: GrantFiled: December 23, 1981Date of Patent: September 10, 1985Assignee: Otsuka Pharmaceutical Company, LimitedInventors: Minoru Uchida, Takao Nishi, Kazuyuki Nakagawa
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Patent number: 4372953Abstract: 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.Type: GrantFiled: February 27, 1981Date of Patent: February 8, 1983Assignee: Otsuka Pharmaceutical Company, LimitedInventors: Minoru Uchida, Takao Nishi, Kazuyuki Nakagawa