Patents by Inventor Masaru Mitsuda
Masaru Mitsuda 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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Publication number: 20240140998Abstract: Provided is a method for artificially and efficiently inducing ectopic embryogenesis without fertilization in a seed plant. The present method includes introducing and expressing, in a seed plant, nucleic acid that includes a base sequence that codes a protein having an embryogenesis induction function.Type: ApplicationFiled: March 2, 2022Publication date: May 2, 2024Applicant: NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGYInventors: MASARU TAKAGI, MIHO IKEDA, NOBUTAKA MITSUDA, HIRONORI TAKASAKI
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Patent number: 10781193Abstract: The present disclosure provides a reaction of a chlorine-containing compound using a flow reactor which is less restricted by a solvent to be used. In the present disclosure, an organic compound is produced by supplying a reaction substrate having at least one functional group which can react with chlorine and is selected from the group consisting of hydroxy group, a thiol group, an amino group, a carboxyl group, a thiocarboxyl group, and an acid amide group, and a chlorine-containing compound to a flow reactor together with a trialkyl amine having 9 to 40 carbon atoms and an organic solvent, and allowing the reaction substrate and the chlorine-containing compound to react with each other.Type: GrantFiled: January 10, 2019Date of Patent: September 22, 2020Assignee: KANEKA CORPORATIONInventors: Hiroaki Yasukouchi, Masaru Mitsuda, Akira Nishiyama, Makoto Funabashi
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Publication number: 20190177262Abstract: The present invention provides a method for safely producing a large amount of chloroformate compound with high yield. The chloroformate compound can be produced by mixing and reacting a solution of triphosgene, an amine and an alcohol compound in a flow reactor. The chloroformate compound can also be produced by mixing and reacting a solution of triphosgene with a solution comprising an amine and an alcohol compound in a flow reactor. The amine is preferably tributylamine, and preferably used in an amount of 0.8 to 3 equivalents relative to an amount of the alcohol compound.Type: ApplicationFiled: January 10, 2019Publication date: June 13, 2019Applicant: KANEKA CORPORATIONInventors: Hiroaki YASUKOUCHI, Makoto FUNABASHI, Akira NISHIYAMA, Toshihiro TAKEDA, Masaru MITSUDA
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Publication number: 20190144404Abstract: The present disclosure provides a reaction of a chlorine-containing compound using a flow reactor which is less restricted by a solvent to be used. In the present disclosure, an organic compound is produced by supplying a reaction substrate having at least one functional group which can react with chlorine and is selected from the group consisting of hydroxy group, a thiol group, an amino group, a carboxyl group, a thiocarboxyl group, and an acid amide group, and a chlorine-containing compound to a flow reactor together with a trialkyl amine having 9 to 40 carbon atoms and an organic solvent, and allowing the reaction substrate and the chlorine-containing compound to react with each other.Type: ApplicationFiled: January 10, 2019Publication date: May 16, 2019Applicant: KANEKA CORPORATIONInventors: Hiroaki YASUKOUCHI, Masaru MITSUDA, Akira NISHIYAMA, Makoto FUNABASHI
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Patent number: 9982014Abstract: The present invention is to provide a method for the efficient production on an industrial scale of SS-31 (D-Arg-Dmt-Lys-Phe-NH2), which is an SS peptide. According to the present invention, the desired SS-31 is produced by efficiently synthesizing a tetrapeptide compound as a precursor of SS-31 and improving the tetrapeptide purity by crystallization.Type: GrantFiled: October 23, 2014Date of Patent: May 29, 2018Assignees: Kaneka Corporation, Stealth BioTherapeutics CorpInventors: Yoshinori Hirai, Akira Nishiyama, Masaru Mitsuda
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Publication number: 20160264623Abstract: The present invention is to provide a method for the efficient production on an industrial scale of SS-31 (D-Arg-Dmt-Lys-Phe-NH2), which is an SS peptide. According to the present invention, the desired SS-31 is produced by efficiently synthesizing a tetrapeptide compound as a precursor of SS-31 and improving the tetrapeptide purity by crystallization.Type: ApplicationFiled: October 23, 2014Publication date: September 15, 2016Inventors: Yoshinori Hirai, Akira Nishiyama, Masaru Mitsuda
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Patent number: 9346850Abstract: The present invention is related to a method of producing a peptide, characterized in contacting a reaction mixture with a base after a condensation reaction to hydrolyze while a basic condition is maintained until a ratio of a remaining unreacted active ester of an acid component is decreased to 1% or less in a liquid phase peptide synthesis method. According to the invention, a target peptide of high purity can be simply and efficiently produced by a continuous liquid phase synthesis method. Further, the present invention is related to a method of producing a peptide, characterized in using an amide-type solvent immiscible with water in a liquid phase peptide synthesis method. According to the invention, various peptides can be produced by the liquid phase synthesis method without being restricted by the amino acid sequence of the target peptide.Type: GrantFiled: March 11, 2014Date of Patent: May 24, 2016Assignee: KANEKA CORPORATIONInventors: Hiroshi Murao, Ken-ichiro Morio, Masaru Mitsuda
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Publication number: 20140288268Abstract: The present invention is related to a method of producing a peptide, characterized in contacting a reaction mixture with a base after a condensation reaction to hydrolyze while a basic condition is maintained until a ratio of a remaining unreacted active ester of an acid component is decreased to 1% or less in a liquid phase peptide synthesis method. According to the invention, a target peptide of high purity can be simply and efficiently produced by a continuous liquid phase synthesis method. Further, the present invention is related to a method of producing a peptide, characterized in using an amide-type solvent immiscible with water in a liquid phase peptide synthesis method. According to the invention, various peptides can be produced by the liquid phase synthesis method without being restricted by the amino acid sequence of the target peptide.Type: ApplicationFiled: March 11, 2014Publication date: September 25, 2014Applicant: KANEKA CORPORATIONInventors: Hiroshi MURAO, Ken-ichiro MORIO, Masaru MITSUDA
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Patent number: 8716439Abstract: The present invention is related to a method of producing a peptide, characterized in contacting a reaction mixture with a base after a condensation reaction to hydrolyze while a basic condition is maintained until a ratio of a remaining unreacted active ester of an acid component is decreased to 1% or less in a liquid phase peptide synthesis method. According to the invention, a target peptide of high purity can be simply and efficiently produced by a continuous liquid phase synthesis method. Further, the present invention is related to a method of producing a peptide, characterized in using an amide-type solvent immiscible with water in a liquid phase peptide synthesis method. According to the invention, various peptides can be produced by the liquid phase synthesis method without being restricted by the amino acid sequence of the target peptide.Type: GrantFiled: July 31, 2006Date of Patent: May 6, 2014Assignee: Kaneka CorporationInventors: Hiroshi Murao, Ken-ichiro Morio, Masaru Mitsuda
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Patent number: 8383833Abstract: The present application relates to a method for producing an optically active ?-amino acid derivative, comprising steps of reacting an ?-haloester derivative represented by the general formula (1): of which alcohol part of the ester group is an optically active alcohol derivative, with an amine compound; then deprotecting the obtained compound; further carrying out an ester exchange reaction. According to the present invention method, it is possible to easily produce an optically active ?-amino acid ester derivative which is useful as an intermediate for drugs with high selectivity.Type: GrantFiled: June 2, 2009Date of Patent: February 26, 2013Assignee: Kaneka CorporationInventors: Shohei Yamamoto, Akio Fujii, Masaru Mitsuda
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Patent number: 8278475Abstract: This invention relates to processes for the production of optically active 2-(disubstituted aryl)cyclopropylamine compounds and optically active 2-(disubstituted aryl) cyclopropane carboxamide compounds which are useful intermediates for the preparation of pharmaceutical agents, and in particular the compound [1S-(1?,2?,3?(1S*,2R*),5?]-3-[7-[2-(3,4-difluorophenyl)-cyclopropyl]amino]-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl)-5-(2-hydroxyethoxy)-cyclopentane-1,2-diol.Type: GrantFiled: August 26, 2011Date of Patent: October 2, 2012Assignee: AstraZeneca ABInventors: Masaru Mitsuda, Tadashi Moroshima, Kentaro Tsukuya, Kazuhiko Watabe, Masahiko Yamada
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Patent number: 8273883Abstract: The objective of the present invention is to produce an optically active 2-arylpiperazine derivative useful as a synthetic intermediate for pharmaceutical products and agricultural chemicals from inexpensive and readily available starting material by an industrially practicable method. The objective can be accomplished by treating an optically active substituted aminodiol derivative produced from an optically active styrene oxide derivative with a sulfonating agent in the presence of a base, and then reacting an amine compound to obtain the 2-arylpiperazine derivative. Especially, an optically active 1-unsubstituted-2-arylpiperazine derivative can be produced by treating an optically active 1-allyl-2-arylpiperazine derivative with water in the presence of a transition metal catalyst for deallylation.Type: GrantFiled: February 5, 2008Date of Patent: September 25, 2012Assignee: Kaneka CorporationInventors: Masatoshi Ohnuki, Akira Nishiyama, Masaru Mitsuda
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Patent number: 8252919Abstract: The present invention relates to a method for producing a 2?-hydroxy-protected nucleoside derivative by reacting a ribonucleoside with an acylating or a carbamoylating reagent in the presence of a metal complex consisting of a copper compound and an optically active ligand. By the method according to the present invention, a 2?-hydroxy-protected ribonucleoside derivative, which is an important intermediate for producing an oligonucleoside, can be easily produced with good regioselectivity from a nucleoside derivative of which 2?,3?-hydroxy groups are not protected.Type: GrantFiled: February 26, 2009Date of Patent: August 28, 2012Assignee: Kaneka CorporationInventors: Hirofumi Maeda, Akio Fujii, Masaru Mitsuda
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Patent number: 8207370Abstract: It is an objective of the present invention to produce an anti-form of an optically active ?-hydroxy-?-aminocarboxylic acid ester efficiently, simply and industrially advantageously. The objective can be accomplished by directly and selectively producing the anti-form of the optically active ?-hydroxy-?-aminocarboxylic acid ester by asymmetric reduction of a ?-keto-?-aminocarboxylic acid ester using an optically active amine complex as a catalyst. Further, the ?-keto-?-aminocarboxylic acid ester as a raw material can be produced at a high yield by reacting a glycine derivative with a carboxylic acid derivative.Type: GrantFiled: September 26, 2007Date of Patent: June 26, 2012Assignee: Kaneka CorporationInventors: Tatsuya Honda, Tatsuyoshi Tanaka, Masaru Mitsuda
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Publication number: 20120136167Abstract: This invention relates to processes for the production of optically active 2-(disubstituted aryl)cyclopropylamine compounds and optically active 2-(disubstituted aryl) cyclopropane carboxamide compounds which are useful intermediates for the preparation of pharmaceutical agents, and in particular the compound [1S-(1?,2?,3?(1S*,2R*),5?]-3-[7-[2-(3,4-difluorophenyl)-cyclopropyl]amino]-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl)-5-(2-hydroxyethoxy)-cyclopentane-1,2-diol.Type: ApplicationFiled: August 26, 2011Publication date: May 31, 2012Applicant: ASTRAZENECA ABInventors: Masaru Mitsuda, Tadashi Moroshima, Kentaro Tsukuya, Kazuhiko Watabe, Masahiko Yamada
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Patent number: 8058471Abstract: The present invention has its object to provide a method for producing an optically active hydroxycarboxylic acid derivative which is an intermediate important for production of medicines, agrochemicals, chemical products, and so on. The production method of the present invention comprises: carrying out a hydrogen-transfer reduction of a ketocarboxylic acid or a salt thereof by the reaction of an optically active diamine complex to produce an optically active hydroxycarboxylic acid derivative. According to the present invention, it is possible to safely and efficiently produce an industrially-useful optically active hydroxycarboxylic acid derivative.Type: GrantFiled: August 8, 2007Date of Patent: November 15, 2011Assignee: Kaneka CorporationInventors: Susumu Amano, Akio Fujii, Shohei Yamamoto, Masaru Mitsuda
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Patent number: 8026396Abstract: This invention relates to processes for the production of optically active 2-(disubstituted aryl)cyclopropylamine compounds and optically active 2-(disubstituted aryl)cyclopropane carboxamide compounds which are useful intermediates for the preparation of pharmaceutical agents, and in particular the compound [1S-(1?,2?,3?(1S*,2R*),5?)]-3-[7-[2-(3,4-difluorophenyl)-cyclopropyl]amino]-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl)-5-(2-hydroxyethoxy)-cyclopentane-1,2-diol.Type: GrantFiled: August 11, 2010Date of Patent: September 27, 2011Assignee: AstraZeneca ABInventors: Masaru Mitsuda, Tadashi Moroshima, Kentaro Tsukuya, Kazuhiko Watabe, Masahiko Yamada
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Publication number: 20110166354Abstract: The present application relates to a method for producing an optically active ?-amino acid derivative, comprising steps of reacting an ?-haloester derivative represented by the general formula (1): of which alcohol part of the ester group is an optically active alcohol derivative, with an amine compound; then deprotecting the obtained compound; further carrying out an ester exchange reaction. According to the present invention method, it is possible to easily produce an optically active ?-amino acid ester derivative which is useful as an intermediate for drugs with high selectivity.Type: ApplicationFiled: June 2, 2009Publication date: July 7, 2011Inventors: Shohei Yamamoto, Akio Fujii, Masaru Mitsuda
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Patent number: 7947722Abstract: The objective of the present invention is to provide an optically active imidazolidinone derivative widely usable for synthesizing an optically active amino acid, a method of easily producing the derivative, and a method of easily producing an optically active amino acid by using the derivative. The objective can be achieved by producing an optically active amino acid using a novel optically active imidazolidinone derivative represented by a general formula (3) and the like. According to the method of the present invention, an optically active imidazolidinone derivative can be obtained by preferential crystallization from a mixture of isomers of the imidazolidinone derivative. Therefore, an optically active amino acid can be easily and stereoselectively produced without cumbersome procedures required for the conventional methods, such as resolution of diastereomers, synthesis from an optically active amino acid and resolution of isomers by silica gel column chromatography.Type: GrantFiled: May 14, 2007Date of Patent: May 24, 2011Assignee: Kaneka CorporationInventors: Yasuhiro Saka, Akio Fujii, Kazumi Okuro, Masaru Mitsuda
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Publication number: 20110009609Abstract: The present invention relates to a method for producing a 2?-hydroxy-protected nucleoside derivative by reacting a ribonucleoside with an acylating reagent in the presence of a metal complex consisting of a copper compound and an optically active ligand. By the method according to the present invention, a 2?-hydroxy-protected ribonucleoside derivative, which is an important intermediate for producing an oligonucleoside, can be easily produced with good regioselectivity from a nucleoside derivative of which 2?,3?-hydroxy groups are not protected.Type: ApplicationFiled: February 26, 2009Publication date: January 13, 2011Inventors: Hirofumi Maeda, Akio Fujii, Masaru Mitsuda