Patents by Inventor Kentaro Hirai
Kentaro Hirai has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Patent number: 4900749Abstract: Novel isoprenoidamine compounds (I) which show antiulcer activity are provided.Type: GrantFiled: March 10, 1986Date of Patent: February 13, 1990Assignee: Shionogi & Co., Ltd.Inventors: Saichi Matsumoto, Masami Doteuchi, Takuji Mizui, Kentaro Hirai
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Patent number: 4882338Abstract: A compound of the formula: ##STR1## (wherein R is hydrogen, hydroxy, methoxy, acetoxy, acetoxymethyl or trifluoromethyl;R.sup.1, R.sup.2, R.sup.3 and R.sup.4 each is hydrogen, hydroxy, optionally substituted C.sub.1 -C.sub.5 alkoxy, acetoxy, propynyloxy, allyloxy or benzyloxy; or R.sup.2 and R.sup.3 taken together form methylenedioxy;R.sup.5 is hydrogen, hydroxymethyl, C.sub.2 -C.sub.4 alkoxycarbonyl, C.sub.2 -C.sub.5 acyloxymethyl or phthalidyl; and n is 0 or 1 except for the case in which R is methoxy and R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 each is hydrogen) or its pharmaceutically acceptable acid addition salt, being useful as anti-ulcer agents is provided through several routes.Type: GrantFiled: July 1, 1987Date of Patent: November 21, 1989Assignee: Shionogi & Co., Ltd.Inventors: Kentaro Hirai, Yukio Mizushima
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Patent number: 4839365Abstract: A compound of the formula: ##STR1## (wherein R.sup.1 is hydrogen, C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkoxy, C.sub.1 -C.sub.5 alkoxycarbonyl, or trifluoromethyl; R.sup.2 is hydrogen, C.sub.1 -C.sub.5 alkoxycarbonyl, C.sub.6 -C.sub.12 aryloxycarbonyl, C.sub.1 -C.sub.5 alkanoyloxy-C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkoxycarbonyloxy-C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 acylamino-C.sub.1 -C.sub.5 alkyl, 2-hydroxy-1-C.sub.2 -C.sub.5 alkenyl, phthalimido-C.sub.1 -C.sub.5 alkyl, halogeno-C.sub.1 -C.sub.5 alkoxycarbonyl-C.sub.1 -C.sub.5 alkyl, hydroxy-C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkylthio-C.sub.1 -C.sub.5 alkyl, or C.sub.1 -C.sub.5 alkylsulfinyl-C.sub.1 -C.sub.5 alkyl; ##STR2## m is an integer of 0 or 1; R.sup.3 and R.sup.4 each is hydrogen, halogen, cyano, C.sub.1 -C.sub.5 alkyl, amino, C.sub.1 -C.sub.5 alkoxy, C.sub.6 -C.sub.12 aryl-C.sub.1 -C.sub.5 alkoxy, C.sub.1 -C.sub.5 alkoxycarbonyl, fluoro-C.sub.1 -C.sub.5 alkoxy, C.sub.1 -C.sub.Type: GrantFiled: May 6, 1988Date of Patent: June 13, 1989Assignee: Shinogi & Co., Ltd.Inventors: Kentaro Hirai, Yukio Mizushima, Masami Doteuchi
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Patent number: 4564623Abstract: An aminoalkylbenzene derivative of the formula: ##STR1## [wherein A is oxygen or sulfur;Y is oxo, thioxo, or cyanoimino;a is an integer of 1 to 3;b is an integer of 0 to 3;c is an integer of 1 to 4;R.sup.1 is alkyl;R.sup.2 is hydrogen or alkyl; orR.sup.1 and R.sup.2 taken together represent pyrrolidinyl;R is hydrogen, cycloaklkyl, trihaloalkyl, alkoxy, dialkylamino, aryl, aroyl, heterocyclic group, or a group of the formula: ##STR2## (wherein R.sup.3 is hydrogen, halogen, amino, alkyl, alkylamino, dialkylamino, alkylthio, or aryloxy;R.sup.4 is hydrogen, alkyl, alkenyl, aryl, or heterocyclic group; orR.sup.3 and R.sup.4 taken together represent alkylidene or aralkylidene);with the proviso that the above aryl, aroyl, and heterocyclic group can be substituted by 1 to 3 substituents] and its pharmaceutically acceptable acid addition salts being useful as histamine H.sub.2 blockers, especially peptic ulcer remedies, are provided via several routes.Type: GrantFiled: January 25, 1984Date of Patent: January 14, 1986Assignee: Shionogi & Co., Ltd.Inventors: Kentaro Hirai, Teruyuki Ishiba, Shigeru Matsutani, Itsuo Makino, Toshio Fujishita, Masami Doteuchi, Koichi Otani
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Patent number: 4492794Abstract: A compound of the formula: ##STR1## wherein R is hydrogen, C.sub.1 -C.sub.5 alkanoyl or substituted sulfonyl, which is useful as a synthetic intermediate to 2-guanidino-4-[2-(formamido)ethylthiomethyl]thiazole, histamine H.sub.2 receptor antagonist.Type: GrantFiled: April 26, 1983Date of Patent: January 8, 1985Assignee: Shionogi & Co., Ltd.Inventor: Kentaro Hirai
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Patent number: 4482566Abstract: An aminoalkylbenzene derivative of the formula: ##STR1## [wherein A is oxygen or sulfur;Y is oxo, thioxo, or cyanoimino;a is an integer of 1 to 3;b is an integer of 0 to 3;c is an integer of 1 to 4;R.sup.1 is alkyl;R.sup.2 is hydrogen or alkyl; orR.sup.1 and R.sup.2 taken together represent pyrrolidinyl;R is hydrogen, cycloalkyl, trihaloalkyl, alkoxy, dialkylamino, aryl, aroyl, heterocyclic group, or a group of the formula: ##STR2## (wherein R.sup.3 is hydrogen, halogen, amino, alkyl, alkylamino, dialkylamino, alkylthio, or aryloxy;R.sup.4 is hydrogen, alkyl, alkenyl, aryl, or heterocyclic group; orR.sup.3 and R.sup.4 taken together represent alkylidene or aralkylidene);with the proviso that the above aryl, aroyl, and heterocyclic group can be substituted by 1 to 3 substituents] and its pharmaceutically acceptable acid addition salts being useful as histamine H.sub.2 blockers, especially peptic ulcer remedies, are provided via several routes.Type: GrantFiled: June 25, 1981Date of Patent: November 13, 1984Assignee: Teikoku Hormone Mfg. Co., Ltd.Inventors: Kentaro Hirai, Teruyuki Ishiba, Shigeru Matsutani, Itsuo Makino, Toshio Fujishita, Masami Doeteuchi, Koichi Otani
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Patent number: 4476133Abstract: 4,1-Benzoxazepines of the following formula are novel central nervous system: ##STR1## wherein R is hydrogen or C.sub.1 to C.sub.5 alkyl;X is hydrogen, halogen, or nitro;Y is phenyl, 2-halophenyl, 4-halophenyl, 2-trifluoromethylphenyl, or pyridyl;and ##STR2## is a group of the formula: ##STR3## (wherein Q is oxygen, sulfur, or hydrazono, with a proviso that, when Y is phenyl or 2-halophenyl and R is hydrogen, Q is neither oxygen nor sulfur;R.sup.1 is hydrogen, halogen, C.sub.1 to C.sub.5 alkyl, C.sub.1 to C.sub.5 alkylthio, 5- or 6-membered heterocycle or C.sub.1 to C.sub.5 alkyl substituted by a substituent selected from the group consisting of halogen, hydroxy, mercapto, C.sub.1 to C.sub.5 alkoxy, C.sub.1 to C.sub.5 alkanoyloxy, C.sub.1 to C.sub.5 alkylthio, C.sub.7 to C.sub.9 aralkyldithio, C.sub.2 to C.sub.10 dialkylamino, C.sub.3 to C.sub.15 dialkylaminoalkoxy, C.sub.3 to C.sub.15 dialkylaminoalkylthio, and 5- or 6-membered heterocycle;R.sup.2 is C.sub.1 to C.sub.5 alkyl;and R.sup.3 is C.sub.1 to C.sub.Type: GrantFiled: July 13, 1982Date of Patent: October 9, 1984Assignee: Shionogi & Co., Ltd.Inventors: Kentaro Hirai, Shigeru Matsutani, Itsuo Makino, Teruyuki Ishiba
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Patent number: 4433154Abstract: Bis(carboxamide) derivatives being useful as histamine H.sub.2 receptor antagonists or anti-peptic ulcer agents are provided from certain dicarboxylic acid derivatives.Type: GrantFiled: December 7, 1981Date of Patent: February 21, 1984Assignee: Shionogi & Company, LimitedInventor: Kentaro Hirai
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Patent number: 4374842Abstract: 4,1-Benzoxazepines of the following formula are central nervous system drugs: ##STR1## wherein R is hydrogen or C.sub.1 to C.sub.5 alkyl; X is hydrogen, halogen, or nitro; Y is phenyl, 2-halophenyl, 4-halophenyl, 2-trifluoromethylphenyl, or pyridyl; and ##STR2## is a group of the formula: ##STR3## (wherein Q is oxygen, sulfur, or hydrazono, with a proviso that, when Y is phenyl or 2-halophenyl and R is hydrogen, Q is neither oxygen nor sulfur;R.sup.1 is hydrogen, halogen, C.sub.1 to C.sub.5 alkyl, C.sub.1 to C.sub.5 alkylthio, 5- or 6-membered heterocycle or C.sub.1 to C.sub.5 alkyl substituted by a substituent selected from the group consisting of halogen, hydroxy, mercapto, C.sub.1 to C.sub.5 alkoxy, C.sub.1 to C.sub.5 alkanoyloxy, C.sub.1 to C.sub.5 alkylthio, C.sub.7 to C.sub.9 aralkyldithio, C.sub.2 to C.sub.10 dialkylamino, C.sub.3 to C.sub.15 dialkylaminoalkoxy, C.sub.3 to C.sub.15 dialkylaminoalkylthio, and 5- or 6-membered heterocycle;R.sup.2 is C.sub.1 to C.sub.5 alkyl;and R.sup.3 is C.sub.1 to C.Type: GrantFiled: April 2, 1981Date of Patent: February 22, 1983Assignee: Shionogi & Co., Ltd.Inventors: Kentaro Hirai, Shigeru Matsutani, Itsuo Makino, Teruyuki Ishiba
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Patent number: 4341704Abstract: 4,1-Benzoxazepines and thia analogs thereof of the formula: ##STR1## (wherein --A--B-- is the following group: ##STR2## (wherein R.sup.1 is hydrogen, C.sub.1 to C.sub.3 alkyl, or C.sub.7 to C.sub.9 aralkyl;R.sup.2 is C.sub.1 to C.sub.3 alkyl or C.sub.1 to C.sub.3 .alpha.-aminoalkyl;R.sup.3 is C.sub.2 to C.sub.6 dialkylamino;R.sup.4 is C.sub.2 to C.sub.6 dialkylamino or C.sub.5 to C.sub.7 alkylpiperazino;R.sup.5 is C.sub.1 to C.sub.3 alkyl; andQ is oxygen or sulfur);D is oxygen or sulfur;X is halogen or nitro;Y is hydrogen or halogen; andZ is hydrogen, C.sub.1 to C.sub.3 alkoxy, or C.sub.3 to C.sub.9 dialkylaminoalkoxy;with the proviso that when --A--B-- is ##STR3## Z is not hydrogen.) useful as novel central nervous system drugs are prepared by various synthetic routes.Type: GrantFiled: June 23, 1981Date of Patent: July 27, 1982Assignee: Shionogi & Co., Ltd.Inventors: Kentaro Hirai, Shigeru Matsutani, Teruyuki Ishiba, Itsuo Makino
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Patent number: 4318858Abstract: A compound of the formula: ##STR1## [wherein R is dimethylamino or 1-pyrrolidinyl;R.sup.1 and R.sup.2 each is hydrogen or C.sub.1 -C.sub.3 alkyl;R.sup.3 is hydrogen, C.sub.1 -C.sub.3 alkyl (optionally substituted by one member selected from the group consisting of cyano, C.sub.1 -C.sub.3 alkoxy, phenyl, and 5- or 6-membered heterocyclic group), C.sub.3 -C.sub.6 cycloalkyl, C.sub.2 -C.sub.5 alkenyl (optionally substituted by one member selected from the group consisting of C.sub.1 -C.sub.3 alkoxy, phenyl, and phenoxy), C.sub.6 -C.sub.10 aryl (optionally substituted by one or two members selected from the group consisting of hydroxy, halogen, nitro, sulfamoyl, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 alkanoyl, C.sub.2 -C.sub.4 alkoxycarbonyl, C.sub.2 -C.sub.4 dialkylamino, and C.sub.1 -C.sub.3 alkanesulfonyl), or 5- or 6-membered heterocyclic group (optionally substituted by one member selected from the group consisting of oxo, halogen, C.sub.1 -C.sub.3 alkyl, and C.sub.1 -C.sub.Type: GrantFiled: December 2, 1980Date of Patent: March 9, 1982Assignee: Shionogi & Co., Ltd.Inventors: Kentaro Hirai, Shigeru Matsutani, Teruyuki Ishiba, Itsuo Makino, Masami Doteuchi, Koichi Otani
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Patent number: 4309433Abstract: An aminoalkylbenzene derivative of the formula: ##STR1## [wherein A is oxygen or sulfur;Y is oxo, thioxo, or cyanoimino;a is an integer of 1 to 3;b is an integer of 0 to 3;c is an integer of 1 to 4;R.sup.1 is alkyl;R.sup.2 is hydrogen or alkyl; orR.sup.1 and R.sup.2 taken together represent pyrrolidinyl;R is hydrogen, cycloalkyl, trihaloalkyl, alkoxy, dialkylamino, aryl, aroyl, heterocyclic group, or a group of the formula: ##STR2## (wherein R.sup.3 is hydrogen, halogen, amino, alkyl, alkylamino, dialkylamino, alkylthio, or aryloxy;R.sup.4 is hydrogen, alkyl, alkenyl, aryl, or heterocyclic group; orR.sup.3 and R.sup.4 taken together represent alkylidene or aralkylidene;with the proviso that the above aryl, aroyl, and heterocyclic group can be substituted by 1 to 3 substituents] and its pharmaceutically acceptable acid addition salts being useful as histamine H.sub.2 blockers, especially peptic ulcer remedies, are provided via several routes.Type: GrantFiled: June 30, 1980Date of Patent: January 5, 1982Assignee: Shionogi & Co., Ltd.Inventors: Kentaro Hirai, Teruyuki Ishiba, Shigeru Matsutani, Itsuo Makino, Toshio Fujishita, Masami Doteuchi, Koichi Otani
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Patent number: 4297280Abstract: 4,1-Benzoxazepines and thia analogs thereof of the formula: ##STR1## (wherein --A--B-- is the following group: ##STR2## (wherein R.sup.1 is hydrogen, C.sub.1 to C.sub.3 alkyl, or C.sub.7 to C.sub.9 aralkyl;R.sup.2 is C.sub.1 to C.sub.3 alkyl or C.sub.1 to C.sub.3 .alpha.-aminoalkyl;R.sup.3 is C.sub.2 to C.sub.6 dialkylamino;R.sup.4 is C.sub.2 to C.sub.6 dialkylamino or C.sub.5 to C.sub.7 alkylpiperazino;R.sup.5 is C.sub.1 to C.sub.3 alkyl; andQ is oxygen or sulfur);D is oxygen or sulfur;X is halogen or nitro;Y is hydrogen or halogen; andZ is hydrogen, C.sub.1 to C.sub.3 alkoxy, or C.sub.3 to C.sub.9 dialkylaminoalkoxy;with the proviso that when --A--B-- is ##STR3## Z is not hydrogen.) useful as novel central nervous system drugs are prepared by various synthetic routes.Type: GrantFiled: November 6, 1979Date of Patent: October 27, 1981Assignee: Shionogi & Co., Ltd.Inventors: Kentaro Hirai, Shigeru Matsutani, Teruyuki Ishiba, Itsuo Makino
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Patent number: 4264499Abstract: A compound of the formula: ##STR1## wherein R is hydrogen, 2-5C alkoxycarbonyl, 1-7C acyl, 1-4C alkylthio, 7-10C phenylalkylthio, phenylthio, halo-phenylthio, disubstituted aminothio, ##STR2## R.sup.1 is hydrogen or halogen; R.sup.2 is halogen or nitro;and its pharmaceutically acceptable acid addition salts.The compounds and salts thereof are useful as psychotropic agents and as anxiolytics, anticonvulsants and hypnotics.Type: GrantFiled: January 10, 1980Date of Patent: April 28, 1981Assignee: Shionogi & Co., Ltd.Inventors: Kentaro Hirai, Toshio Fujishita, Teruyuki Ishiba
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Patent number: 4240957Abstract: Dipeptide derivatives represented by the formula: ##STR1## wherein R represents hydrogen, C.sub.1 -C.sub.6 alkyl group, C.sub.2 -C.sub.7 alkenyl group, C.sub.2 -C.sub.7 cyanoalkyl group, C.sub.2 -C.sub.7 carbamoylalkyl group, C.sub.3 -C.sub.10 dialkylaminoalkyl group or cyclopropylmethyl group, R.sup.1 represents hydrogen, C.sub.1 -C.sub.6 alkyl group, C.sub.7 -C.sub.14 aralkyl group, C.sub.7 -C.sub.14 hydroxyaralkyl group, C.sub.6 -C.sub.12 aryl group, C.sub.2 -C.sub.7 carbamoylalkyl group, C.sub.2 -C.sub.7 carboxyalkyl group, C.sub.1 -C.sub.6 aminoalkyl group, C.sub.4 -C.sub.10 guanidylalkyl group, C.sub.1 -C.sub.6 mercaptoalkyl group, C.sub.2 -C.sub.7 alkylthioalkyl group, C.sub.9 -C.sub.15 indolylalkyl group or C.sub.4 -C.sub.9 imidazolylalkyl group, R.sup.2 represents hydrogen, C.sub.1 -C.sub.6 alkyl group, C.sub.7 -C.sub.14 aralkyl group, C.sub.6 -C.sub.12 aryl group, glycyl group or glycyl-glycyl group, R.sup.3 represents hydrogen, C.sub.1 -C.sub.6 alkyl group or amino-protecting group, R.sup.1 and R.Type: GrantFiled: March 7, 1977Date of Patent: December 23, 1980Assignee: Shionogi & Co., Ltd.Inventors: Kentaro Hirai, Teruyuki Ishiba, Kazuyuki Sasakura, Hirohiko Sugimoto
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Patent number: 4231930Abstract: A compound of the formula: ##STR1## wherein R is hydrogen, 2-5C alkoxycarbonyl, 1-7C acyl, 1-4C alkylthio, 7-10C phenylalkylthio, phenylthio, halo-phenylthio, disubstituted aminothio, ##STR2## R.sup.1 is hydrogen or halogen; R.sup.2 is halogen or nitro;and its pharmaceutically acceptable acid addition salts. The compounds and salts thereof are useful as psychotropic agents and as anxiolytics, anticonvulsants and hypnotics.Type: GrantFiled: March 1, 1979Date of Patent: November 4, 1980Assignee: Shionogi & Co., Ltd.Inventors: Kentaro Hirai, Toshio Fujishita, Teruyuki Ishiba
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Patent number: 4159374Abstract: Triazolyl ketone derivatives of the formula: ##STR1## (wherein R represents lower alkoxy or the group ##STR2## R.sup.4 and R.sup.5 each represents hydrogen, lower alkyl, ##STR3## represents hetero ring selected from pyrrolidino, piperidino, and morpholino; R.sup.1 represents halogen or nitro; R.sup.2 represents hydrogen or lower alkyl; R.sup.3 represents lower alkyl, phenyl, or the group ##STR4## R.sup.6 represents hydrogen, lower alkyl, or benzyl; R.sup.7 and R.sup.8 each represents hydrogen, lower alkyl, or ##STR5## represents hetero ring selected from pyrrolidino, piperidino, and morpholino; and Ar represents phenyl, o-halogenophenyl, or 2-pyridyl) and their pharmaceutically acceptable acid addition salts, being useful as anxiolytics, hypnotics, anticonvulsants, muscle relaxants, or their synthetic intermediates, are prepared by several routes.Type: GrantFiled: June 3, 1977Date of Patent: June 26, 1979Assignee: Shionogi & Co., Ltd.Inventors: Kentaro Hirai, Hirohiko Sugimoto
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Patent number: 4154727Abstract: Dipeptide derivatives represented by the formula: ##STR1## wherein R represents hydrogen, C.sub.1 -C.sub.6 alkyl group, C.sub.2 -C.sub.7 alkenyl group, C.sub.2 -C.sub.7 cyanoalkyl group, C.sub.2 -C.sub.7 carbamoylalkyl group, C.sub.3 -C.sub.10 dialkylaminoalkyl group or cyclopropylmethyl group, R.sup.1 represents hydrogen, C.sub.1 -C.sub.6 alkyl group, C.sub.7 -C.sub.14 aralkyl group, C.sub.7 -C.sub.14 hydroxyaralkyl group, C.sub.6 -C.sub.12 aryl group, C.sub.2 -C.sub.7 carbamoylalkyl group, C.sub.2 -C.sub.7 carboxyalkyl group, C.sub.1 -C.sub.6 aminoalkyl group, C.sub.4 -C.sub.10 guanidylalkyl group, C.sub.1 -C.sub.6 mercaptoalkyl group, C.sub.2 -C.sub.7 alkylthioalkyl group, C.sub.9 -C.sub.15 indolylalkyl group or C.sub.4 -C.sub.9 imidazolylalkyl group, R.sup.2 represents hydrogen, C.sub.1 -C.sub.6 alkyl group, C.sub.7 -C.sub.14 aralkyl group, C.sub.6 -C.sub.12 aryl group, glycyl group or glycyl-glycyl group, R.sup.3 represents hydrogen, C.sub.1 -C.sub.6 alkyl group or amino-protecting group, R.sup.1 and R.Type: GrantFiled: January 6, 1978Date of Patent: May 15, 1979Assignee: Shionogi & Co., Ltd.Inventors: Kentaro Hirai, Teruyuki Ishiba, Kazuyuki Sasakura, Hirohiko Sugimoto
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Patent number: 4147700Abstract: Triazolylbenzophenone derivatives of the formula: ##STR1## (wherein R represents hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 halo-alkyl, the group --(CH.sub.2).sub.n --X--R.sup.5, or the group ##STR2## R.sup.5 represents hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.6 -C.sub.10 aryl, or C.sub.2 -C.sub.8 acyl; X represents sulfur or oxygen; n represents 0, 1, 2, or 3; R.sup.6 and R.sup.7 each represents hydrogen or C.sub.1 -C.sub.6 alkyl; or the group ##STR3## represents pyrrolidino, piperidino, morpholino, or .gamma.-methylpiperazino; R.sup.1 represents hydrogen or halogen; R.sup.2 represents halogen, nitro, or trifluoromethyl; R.sup.3 represents C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 halo-alkyl, C.sub.1 -C.sub.6 azido-alkyl, C.sub.6 -C.sub.10 aryl, C.sub.2 -C.sub.8 acyl, or the group ##STR4## R.sup.4 and R.sup.8 each represents hydrogen, C.sub.1 -C.sub.6 alkyl, or C.sub.7 -C.sub.10 aralkyl; R.sup.9 represents hydrogen or C.sub.1 -C.sub.6 alkyl; R.sup.Type: GrantFiled: December 15, 1977Date of Patent: April 3, 1979Assignee: Shionogi & Co., Ltd.Inventors: Kentaro Hirai, Toshio Fujishita, Teruyuki Ishiba, Hirohiko Sugimoto
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Patent number: 4143048Abstract: Triazolylbenzophenone derivatives of the formula: ##STR1## (wherein R represents hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 halo-alkyl, the group --(CH.sub.2).sub.n --X--R.sup.5, or the group ##STR2## R.sup.5 represents hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.6 -C.sub.10 aryl, or C.sub.2 -C.sub.8 acyl; X represents sulfur or oxygen; n represents 0, 1, 2, or 3; R.sup.6 and R.sup.7 each represents hydrogen or C.sub.1 -C.sub.6 alkyl; or the group ##STR3## represents pyrrolidino, piperidino, morpholino, or .gamma.-methylpiperazino; R.sup.1 represents hydrogen or halogen; R.sup.2 represents halogen, nitro, or trifluoromethyl; R.sup.3 represents C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 halo-alkyl, C.sub.1 -C.sub.6 azido-alkyl, C.sub.6 -C.sub.10 aryl, C.sub.2 -C.sub.8 acyl, or the group ##STR4## R.sup.4 and R.sup.8 each represents hydrogen, C.sub.1 -C.sub.6 alkyl, or C.sub.7 -C.sub.10 aralkyl; R.sup.9 represents hydrogen or C.sub.1 -C.sub.6 alkyl; R.sup.Type: GrantFiled: December 15, 1977Date of Patent: March 6, 1979Assignee: Shionogi & Co., Ltd.Inventors: Kentaro Hirai, Toshio Fujishita, Teruyuki Ishiba, Hirohiko Sugimoto