Patents by Inventor Makoto Sunagawa
Makoto Sunagawa 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: 5231179Abstract: A compound of the formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are each a hydrogen atom, a lower alkyl group, an ar(lower)alkyl group or an aryl group, or R.sub.1 and R.sub.2 may be combined together to form a lower alkylene group and/or R.sub.3 and R.sub.4 are combined together to form a lower alkylene group, or R.sub.1, R.sub.2, R.sub.3 and R.sub.4 may be combined together to form an o-phenylene group, X is a halogen atom and Y is an oxygen atom or a nitrogen atom substituted with lower alkyl or aryl, which is useful as an intermediate in the synthesis of 1.beta.-methylcarbapenem compounds valuable as antibiotics.Type: GrantFiled: April 12, 1991Date of Patent: July 27, 1993Assignee: Sumitomo Pharmaceuticals Company, LimitedInventors: Shiro Terashima, Yoshio Ito, Takeo Kawabata, Kunikazu Sakai, Tamejiro Hiyama, Yoshikazu Kimura, Makoto Sunagawa, Katsumi Tamoto, Akira Sasaki
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Patent number: 5227376Abstract: A compound of the formula: ##STR1## , which is useful as an antimicrobial agent.Type: GrantFiled: August 14, 1992Date of Patent: July 13, 1993Assignee: Sumitomo Pharmaceuticals Co., Ltd.Inventors: Makoto Sunagawa, Akira Sasaki, Hiroshi Yamaga, Masatomo Fukasawa, Hiroshi Nouda
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Patent number: 5216186Abstract: Crystalline palladium tetrakis (triphenylphosphine) which exhibits a specific powder X-ray pattern and is excellent in storage stability is obtained by allowing palladium chloride to react with triphenylphosphine in aprotic polar solvents, treating the reaction mixture with an aqueous hydrazine solution, collecting the resulting crystals by filtration, washing with alcohols and further washing with hydrocarbon solvents.Type: GrantFiled: December 19, 1991Date of Patent: June 1, 1993Assignee: Sumitomo Pharmaceuticals Co., Ltd.Inventors: Makoto Sunagawa, Haruki Matsumura, Yutaka Kitamura
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Patent number: 5134231Abstract: An amino acid compound of the formula: ##STR1## wherein R is a lower alkyl group, R.sub.1 is a hydrogen atom or a protecting group for carboxyl, R.sub.2 is a hydrogen atom, a protecting group for amino, an optionally substituted allyl group of the formula: ##STR2## (wherein R.sub.3 and R.sub.4 are each a hydrogen atom, a lower alkyl group or an aryl group), a beta-hydroxyethyl group in which the hydroxyl group is optionally protected, a formylmethyl group in which the formyl group is optionally protected, a carboxymethyl group in which the carboxyl group is protected or a 2-furylmethyl group and X is an optionally protected carboxyl group, a hydroxymethyl group in which the hydroxyl group is optionally protected or a substituted mercaptomethyl group of the formula:--CH.sub.2 SR.sub.5(wherein R.sub.5 is an aryl group or an ar(lower)alkyl group), which is a useful intermediate in the synthesis of 1-alkylcarbapenem compounds.Type: GrantFiled: January 17, 1991Date of Patent: July 28, 1992Assignee: Sumitomo Pharmaceuticals Company, LimitedInventors: Makoto Sunagawa, Yoshihito Nozaki, Akira Sasaki, Haruki Matsumura
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Patent number: 5122604Abstract: Novel .beta.-lactam compounds belonging to carbapenem or penem derivatives useful as antimicrobial agents or intermediates therefor and a process for producing these compounds are disclosed.Type: GrantFiled: May 21, 1990Date of Patent: June 16, 1992Assignee: Sumitomo Pharmaceuticals Co., Ltd.Inventors: Makoto Sunagawa, Haruki Matsumura, Takaaki Inoue, Masatomo Fukasawa, Masuhiro Kato
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Patent number: 5112966Abstract: A beta-lactam compound of the formula: ##STR1## wherein R.sub.1 is a hydrogen atom, a lower alkyl group or a 1-hydroxy(lower)alkyl group wherein the hydroxyl group is optionally protected, R.sub.2 is a hydrogen atom or a protective group for the nitrogen atom and R.sub.3 is a methyl group, a halomethyl group, a hydroxymethyl group, a protected hydroxymethyl group, a formyl group, a carboxyl group, a lower alkoxycarbonyl group or an ar(lower)alkoxycarbonyl group wherein the aryl group is optionally substituted, or R.sub.2 and R.sub.3 are combined together to form an oxaalkylene group and, when taken together with one nitrogen atom and two carbon atoms adjacent thereto, they represent a six-membered cyclic aminoacetal group, which is useful as a valuable intermediate in the stereospecific production of 1-methylcarbapenem compounds.Type: GrantFiled: October 31, 1985Date of Patent: May 12, 1992Assignee: Sumitomo Pharmaceuticals Company, LimitedInventors: Makoto Sunagawa, Haruki Matsumura, Tsuneo Yano, Akira Sasaki, Shinzi Takata
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Patent number: 5093328Abstract: A beta-lactam compound of the formula: ##STR1## or a pharmaceutically acceptable salt thereof, which is useful as an anti-microbial agent or an intermediate in the synthesis of anti-microbial agents.Type: GrantFiled: March 27, 1987Date of Patent: March 3, 1992Assignee: Sumitomo Pharmaceuticals Company, LimitedInventors: Makoto Sunagawa, Haruki Matsumura, Takaaki Inoue, Masatomo Fukasawa, Masuhiro Kato
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Patent number: 5075435Abstract: A beta-lactam compound of the formula: ##STR1## wherein R.sub.1 is a hydrogen atom, a lower alkyl group or a 1-hydroxy(lower)alkyl group wherein the hydroxyl group is optionally protected, R.sub.2 is a hydrogen atom or a protective group for the nitrogen atom and R.sub.3 is a methyl group, a halomethyl group, a hydroxymethyl group, a protected hydroxymethyl group, a formyl group, a carboxyl group, a lower alkoxycarbonyl group or an ar(lower)alkoxycarbonyl group wherein the aryl group is optionally substituted, or R.sub.2 and R.sub.3 are combined together to form an oxaalkylene group and, when taken together with one nitrogen atom and two carbon atoms adjacent thereto, they represent a six-membered cyclic aminoacetal group, which is useful as a valuable intermediate in the stereospecific production of 1-methylcarbapenem compounds.Type: GrantFiled: June 12, 1990Date of Patent: December 24, 1991Assignee: Sumitomo Pharmaceuticals Company, LimitedInventors: Makoto Sunagawa, Haruki Matsumura, Tsuneo Yano, Akira Sasaki, Shinzi Takata
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Patent number: 4962103Abstract: A compound of the formula: ##STR1## wherein R.sub.1 is a hydrogen atom or a lower alkyl group, R.sub.2 is a hydrogen atom or a conventional protecting group for a carboxyl group, R.sub.0 is a hydrogen atom or a conventional protecting group for a hydroxyl group, X is a protected or unprotected amino group, a carboxyl group, a lower alkoxycarbonyl group, an ar(lower)alkyloxycarbonyl group, a cyano group, a hydroxyl group, a lower alkyloxy group, a lower alkylthio group, a lower alkylsulfonyl group or a group of either one of the following formulas: ##STR2## wherein R.sub.3 and R.sub.4, which may be the same or different, each represents a hydrogen atom or a lower alkyl group, or they are taken together to represent an alkylene chain to form, in combination with the adjacent nitrogen atom, a 3- to 7-membered cyclic amino group,--ZCOR.sub.5 (2)wherein Z represents --NH-- or --O-- and R.sub.Type: GrantFiled: March 17, 1989Date of Patent: October 9, 1990Assignee: Sumitomo Pharmaceuticals Company, LimitedInventors: Makoto Sunagawa, Haruki Matsumura, Takaaki Inoue, Masamoto Fukasawa, Masuhiro Kato
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Patent number: 4943569Abstract: Novel .beta.-lactam compounds belonging to carbapenem or penem derivatives useful as antimicrobial agents or intermediates therefor and a process for producing these compounds are disclosed.Type: GrantFiled: October 8, 1987Date of Patent: July 24, 1990Assignee: Sumitomo Pharmaceuticals Co., Ltd.Inventor: Makoto Sunagawa
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Patent number: 4933333Abstract: Novel .beta.-lactam compounds belonging to carbapenem or penem derivatives useful as antimicrobial agents or intermediates therefor and a process for producing these compounds are disclosed.Type: GrantFiled: October 8, 1987Date of Patent: June 12, 1990Assignee: Sumitomo Pharmaceuticals Co., Ltd.Inventors: Makoto Sunagawa, Haruki Matsumura, Takaaki Inoue, Masatomo Fukasawa, Masuhiro Kato
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Patent number: 4888344Abstract: (4R,5S,6S 8R,2'S,4'S)-3-[4-(2-Dimethylaminocarbonyl)pyrrolidinylthio]-4-methyl-6-(1- hydroxyethyl)-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylic acid of the formula: ##STR1## in a crystalline form, which is useful as an antibiotic agent.Type: GrantFiled: July 30, 1987Date of Patent: December 19, 1989Assignee: Sumitomo Pharmaceuticals Company, LimitedInventors: Makoto Sunagawa, Yutaka Isobe, Yutaka Takeuchi, Haruki Matsumura, Yukio Ozaki, Tetsuo Noguchi
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Patent number: 4742052Abstract: Novel .beta.-lactam compounds classified into penem compounds, a process for preparing the same and use of such .beta.-lactam compounds are disclosed. These .beta.-lactam compounds exhibit excellent antimicrobial activities useful as pharmaceuticals or they are important intermediates for the synthesis of compounds having antimicrobial activities.Type: GrantFiled: July 15, 1982Date of Patent: May 3, 1988Assignee: Sumitomo Pharmaceuticals Company, LimitedInventors: Makoto Sunagawa, Haruki Matsumura, Takaaki Inoue, Masao Enomoto
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Patent number: 4556514Abstract: .beta.-Lactam compounds which are useful as intermediates for the production of carbapenem or penem derivatives and a process for producing the same. The process comprises reacting a Schiff base with diketene in the presence of an imidazole, reducing the acetyl group of the resulting N-protected-3-acetyl-2-azetidinone-4-carboxylic acid ester, and removing the protecting group for a carboxyl group from the resulting 3-(1-hydroxyethyl)-2-azetidinone-4-carboxylic acid derivative.Type: GrantFiled: October 13, 1983Date of Patent: December 3, 1985Assignee: Sumitomo Chemical Company, LimitedInventors: Makoto Sunagawa, Koshiro Goda, Masao Enomoto, Akira Sasaki
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Patent number: 4536334Abstract: A process for preparing a .beta.-lactam derivative having a hydrogen atom on the nitrogen atom of the .beta.-lactam ring, which comprises reacting a .beta.-lactam derivative having a mono- or diarylmethyl group on the nitrogen atom of the .beta.-lactam ring with an acid or ceric ammonium nitrate to cleave the bond between the nitrogen atom and the mono- or diarylmethyl group; and novel .beta.-lactam derivatives useful as intermediates for the synthesis of pharmaceutical agents.Type: GrantFiled: June 30, 1980Date of Patent: August 20, 1985Assignee: Sumitomo Chemical Company, LimitedInventors: Makoto Sunagawa, Haruki Matsumura, Takaaki Inoue, Toshiyuki Hirohashi
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Patent number: 4358620Abstract: Novel 9-aminoalkyl-methanoanthracenes of the formula: ##STR1## wherein A is C.sub.1 -C.sub.4 alkylene or C.sub.3 -C.sub.4 alkenylene and R.sub.1 and R.sub.2 are each hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, C.sub.3 -C.sub.6 cycloalkyl(C.sub.1 -C.sub.3)alkyl, ar(C.sub.1 -C.sub.3)alkyl or polyhalo(C.sub.2 -C.sub.4)alkyl or, when taken together with the adjacent nitrogen atom, they may form a 5 to 7-membered nitrogen-containing heterocyclic ring which may contain an additional hetero atom, and their non-toxic salts, which are useful as anti-anxiety, anti-depressant, major tranquilizer, anti-histamine and anti-allergy drugs and can be prepared through a novel key intermediate, i.e. 9-formyl-9,10-dihydro-9,10-methanoanthracene, by various methods.Type: GrantFiled: April 14, 1980Date of Patent: November 9, 1982Assignee: Sumitomo Chemical Company, LimitedInventors: Makoto Sunagawa, Hiromi Sato, Junki Katsube, Hisao Yamamoto
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Patent number: 4224344Abstract: Novel 9-aminoalkyl-methanoanthracenes of the formula: ##STR1## wherein A is C.sub.1 -C.sub.4 alkylene or C.sub.3 -C.sub.4 alkenylene and R.sub.1 and R.sub.2 are each hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, C.sub.3 -C.sub.6 cycloalkyl(C.sub.1 -C.sub.3)alkyl, ar(C.sub.1 -C.sub.3)alkyl or polyhalo(C.sub.2 -C.sub.4)alkyl or, when taken together with the adjacent nitrogen atom, they may form a 5 to 7-membered nitrogen-containing heterocyclic ring which may contain an additional hetero atom, and their non-toxic salts, which are useful as anti-anxiety, anti-depressant, major tranquilizer, anti-histamine and anti-allergy drugs and can be prepared through a novel key intermediate, i.e., 9-formyl-9,10-dihydro-9,10-methanoanthracene, by various methods.Type: GrantFiled: December 11, 1975Date of Patent: September 23, 1980Assignee: Sumitomo Chemical Company, LimitedInventors: Makoto Sunagawa, Hiromi Sato, Junki Katsube, Hisao Yamamoto
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Patent number: 4199646Abstract: A heat-activatable, pressure-sensitive adhesive tape or sheet in which the pressure-sensitive, bonding function arises on heating, which comprises a backing material having thereon a layer of a heat-activatable, pressure-sensitve adhesive having an apparent modulus of elasticity of about 10 to 300 kg/cm.sup.2 at normal temperature, the adhesive comprising a mixture of(a) 100 parts by weight of a copolymer of (i) an alkyl acrylate ester or an alkyl methacrylate ester and (ii) a polymerizable monomer having a functional group, and(b) about 50 to 200 parts by weight of a reactive hot-melt resin that is miscible with the copolymer (a), has a melting point of about 60.degree. C. or higher, and has at least one functional group capable of reacting with the functional group of the copolymer (a), either directly or through a crosslinking agent.Type: GrantFiled: August 9, 1978Date of Patent: April 22, 1980Assignee: Nitto Electric Industrial Co., Ltd.Inventors: Yutaka Hori, Makoto Sunagawa, Naoki Matsuoka
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Patent number: 4169146Abstract: Novel morpholine compounds of the formula: ##STR1## wherein R.sub.1 represents hydrogen or C.sub.1 -C.sub.4 alkyl, R.sub.2 represents hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.5 alkenyl, C.sub.3 -C.sub.5 alkynyl, aryl-(C.sub.1 -C.sub.4)alkyl, (C.sub.3 -C.sub.6)cycloalkyl(C.sub.1 -C.sub.4)alkyl, polyhalo(C.sub.2 -C.sub.4) alkyl or hydroxy(C.sub.2 -C.sub.4)alkyl, A represents straight or branched C.sub.2 -C.sub.4 alkylene, B represents a divalent radical selected from the group consisting of --CH.sub.2 --CH.sub.2 --, --CH.dbd.CH--, ##STR2## --CH.sub.2 --O--, --CH.sub.2 --S--, --S-- and --O--, >D--E-- represents a trivalent radical selected from the group consisting of >CH--CH.sub.2 -- and >C.dbd.CH-- and C.sub.1 and C.sub.2 each represent 1,2-phenylene optionally substituted with one or more substituents selected from the group consisting of halogen, C.sub.1 -C.sub.4 alkyl and C.sub.1 -C.sub.Type: GrantFiled: June 30, 1977Date of Patent: September 25, 1979Assignee: Sumitomo Chemical Company, LimitedInventors: Junki Katsube, Atsuyuki Kojima, Makoto Sunagawa, Yoshinori Takashima, Yoshito Kameno, Hisao Yamamoto
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Patent number: 4085210Abstract: Novel morpholine compounds of the formula: ##STR1## wherein R.sub.1 represents hydrogen or C.sub.1 -C.sub.4 alkyl, R.sub.2 represents hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.5 alkenyl, C.sub.3 -C.sub.5 alkynyl, aryl-(C.sub.1 -C.sub.4)alkyl, (C.sub.3 -C.sub.6)cycloalkyl(C.sub.1 -C.sub.4)alkyl, polyhalo(C.sub.2 -C.sub.4)alkyl or hydroxy(C.sub.2 -C.sub.4)alkyl, A represents straight or branched C.sub.2 -C.sub.4 alkylene, B represents a divalent radical selected from the group consisting of --CH.sub.2 --CH.sub.2 --, --CH.dbd.CH--, ##STR2## --CH.sub.2 --O--, --CH.sub.2 --S--, --S-- and --O--, >D --E-- represents a trivalent radical selected from the group consisting of >CH--CH.sub.2 -- and >C.dbd.CH-- and C.sub.1 and C.sub.2 each represent 1,2-phenylene optionally substituted with one or more substituents selected from the group consisting of halogen, C.sub.1 -C.sub.4 alkyl and C.sub.1 -C.sub.Type: GrantFiled: January 6, 1976Date of Patent: April 18, 1978Assignee: Sumitomo Chemical Company, LimitedInventors: Junki Katsube, Atsuyuki Kojima, Makoto Sunagawa, Yoshinori Takashima, Yoshito Kameno, Hisao Yamamoto