Patents by Inventor Tsutomu Katsuki

Tsutomu Katsuki 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).

  • Patent number: 8410295
    Abstract: A complex, and a process for producing the same, represented by any of the following formulae (I), (I?), (II), (II?), (III), (III?), (IV), and (IV?): where: R1s are independently an alkyl group or an aryl group; R2s are independently a hydrogen atom, an alkyl group, or an aryl group; R3s are independently an alkyl group or an aryl group, provided that two R3s are optionally bonded with each other to form a ring; R4s are independently a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a nitro group, or a cyano group; and M is TiY2, where Y is Cl or alkoxide or the complex forms a di-?-oxo dimer where Y is a ?-oxo ligand.
    Type: Grant
    Filed: March 21, 2012
    Date of Patent: April 2, 2013
    Assignee: Japan Science and Technology Agency
    Inventors: Tsutomu Katsuki, Kazuhiro Matsumoto, Yuji Sawada
  • Patent number: 8394974
    Abstract: [PROBLEMS] To provide an efficient process for producing an optically active chromene oxide compound which is an important intermediate for a benzopyran compound effective in the treatment of arrhythmia. [MEANS FOR SOLVING PROBLEMS] The process for producing an optically active chromene oxide compound comprises using an optically active titanium complex represented by, e.g., the formula (1) or (2) as a catalyst to asymmetrically oxidize an optically active chromene compound with high enantioselectivity in high chemical yield.
    Type: Grant
    Filed: March 9, 2007
    Date of Patent: March 12, 2013
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Shoichi Kondo, Kowichiro Saruhashi, Hisayuki Watanabe, Tsutomu Katsuki
  • Patent number: 8367871
    Abstract: An optically active sulfoxide compound that is useful as an intermediate for synthesis or an active ingredient of a physiologically active substance such as a pharmaceutical agent is produced at a high optical purity. A process for producing an optically active sulfoxide compound of formula (4) comprises oxidizing a sulfide compound of formula (3) in the presence of an optically active metal complex of formula (1), (1?), (2) or (2?) by using an oxidizing agent. The present invention is also directed to the optically active metal complex.
    Type: Grant
    Filed: March 10, 2008
    Date of Patent: February 5, 2013
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Tsutomu Katsuki, Hiromichi Egami
  • Publication number: 20120178954
    Abstract: A complex, and a process for producing the same, represented by any of the following formulae (I), (I?), (II), (II?), (III), (III?), (IV), and (IV?): where: R1s are independently an alkyl group or an aryl group; R2s are independently a hydrogen atom, an alkyl group, or an aryl group; R3s are independently an alkyl group or an aryl group, provided that two R3s are optionally bonded with each other to form a ring; R4s are independently a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a nitro group, or a cyano group; and M is TiY2, where Y is Cl or alkoxide or the complex forms a di-?-oxo dimer where Y is a ?-oxo ligand.
    Type: Application
    Filed: March 21, 2012
    Publication date: July 12, 2012
    Applicant: JAPAN SCIENCE AND TECHNOLOGY AGENCY
    Inventors: Tsutomu KATSUKI, Kazuhiro MATSUMOTO, Yuji SAWADA
  • Patent number: 8217184
    Abstract: The present invention provides an efficient production method of an optically active cis-silylolefin oxide compound useful as an intermediate for various compounds. A production method of an optically active cis-silylolefin oxide compound by subjecting an optically active cis-silylolefin compound to an asymmetric oxidation with a high enantioselectivity and a high chemical yield by utilizing as a catalyst, an optically active titanium complex of Formula (1), Formula (2): or the like.
    Type: Grant
    Filed: March 11, 2010
    Date of Patent: July 10, 2012
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Tsutomu Katsuki, Kazuhiro Matsumoto, Takuya Kubo
  • Patent number: 8163941
    Abstract: There is provided a method for industrially producing optically active epoxy compounds by asymmetrically epoxidizing prochiral unsaturated compounds with an oxidant using as a catalyst a single substance or a di-?-oxo dimer derived therefrom represented by any of the following formulae (I), (I?), (II), (II?), (III), (III?), (IV), and (IV?): [wherein R1s are independently an alkyl group or an aryl group; R2s are independently an alkyl group or an aryl group; R3s are independently an alkyl group or an aryl group, provided that two R3s may be bonded with each other to form a ring; R4s are independently a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a nitro group, or a cyano group; M is TiY2 (Y is Cl, alkoxide, or a ?-oxo ligand)].
    Type: Grant
    Filed: December 27, 2005
    Date of Patent: April 24, 2012
    Assignee: Japan Science and Technology Agency
    Inventors: Tsutomu Katsuki, Kazuhiro Matsumoto, Yuji Sawada
  • Patent number: 7928257
    Abstract: This invention provides a method for producing an optically active aziridine compound or amine compound, which uses as a catalyst a Ru(salen)(CO) complex represented by the following formula (I) or its enantiomer having a high stability, in a high turnover number (TON) and a high enantioselectivity. In the formula (I), Ar is represented by the following formula (VI) or (VII), wherein in the formula (VI), Xs are independently a halogen or a halogenated alkyl group and R1 and R2s are independently hydrogen or an alkyl group or a trialkylsilyl group having a carbon number of 1-4, and in the formula (VII), R3 is a bulky group.
    Type: Grant
    Filed: January 5, 2010
    Date of Patent: April 19, 2011
    Assignee: Japan Science and Technology Agency
    Inventors: Tsutomu Katsuki, Kazufumi Omura, Tatsuya Uchida, Ryo Irie
  • Patent number: 7897819
    Abstract: This invention provides a method for producing an optically active aziridine compound or amine compound, which uses as a catalyst a Ru(salen)(CO) complex represented by the following formula (I) or its enantiomer having a high stability, in a high turnover number (TON) and a high enantioselectivity. In the formula (I), Ar is represented by the following formula (VI) or (VII), wherein in the formula (VI), Xs are independently a halogen or a halogenated alkyl group and R1 and R2s are independently hydrogen or an alkyl group or a trialkylsilyl group having a carbon number of 1-4, and in the formula (VII), R3 is a bulky group.
    Type: Grant
    Filed: January 5, 2010
    Date of Patent: March 1, 2011
    Assignee: Japan Science and Technology Agency
    Inventors: Tsutomu Katsuki, Kazufumi Omura, Tatsuya Uchida, Ryo Irie
  • Publication number: 20100305338
    Abstract: The present invention provides an efficient production method of an optically active cis-silylolefin oxide compound useful as an intermediate for various compounds. A production method of an optically active cis-silylolefin oxide compound by subjecting an optically active cis-silylolefin compound to an asymmetric oxidation with a high enantioselectivity and a high chemical yield by utilizing as a catalyst, an optically active titanium complex of Formula (1), Formula (2): or the like.
    Type: Application
    Filed: March 11, 2010
    Publication date: December 2, 2010
    Applicant: NISSAN CHEMICAL INDUSTRIES, LTD.
    Inventors: Tsutomu KATSUKI, Kazuhiro MATSUMOTO, Takuya KUBO
  • Patent number: 7812184
    Abstract: [Problem] To provide a production method of optically active epoxy compound, and a complex used for the production method and a production method of the complex. [Means for solving the problem] The skeleton that is necessary for expressing a high catalyst activity of optically active titanium salan complex of formulae (1) and (1?) and the substituent that is useful therefor and the position of the substituent are identified, and it is found that optically active epoxy compounds can be produced with a high enantioselectivity and a high chemical yield compared with a case where the prior optically active titanium salan complex is used. The production method comprises subjecting a prochiral compound (formula (4), (5) or (6)) having carbon-carbon double bond in the molecule to asymmetric epoxidation to produce an optically active epoxy compound (formula (7), (8) or (9)). The present invention relates also to a complex used for the production method and a production method of the complex.
    Type: Grant
    Filed: November 8, 2007
    Date of Patent: October 12, 2010
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Shoichi Kondo, Kazuhiro Matsumoto, Yuji Sawada, Tsutomu Katsuki
  • Patent number: 7754899
    Abstract: This invention provides a method for producing an optically active aziridine compound or amine compound, which uses as a catalyst a Ru(salen)(CO) complex represented by the following formula (I) or its enantiomer having a high stability, in a high turnover number (TON) and a high enantioselectivity. In the formula (I), Ar is represented by the following formula (VI) or (VII), wherein in the formula (VI), Xs are independently a halogen or a halogenated alkyl group and R1 and R2s are independently hydrogen or an alkyl group or a trialkylsilyl group having a carbon number of 1-4, and in the formula (VII), R3 is a bulky group.
    Type: Grant
    Filed: June 16, 2005
    Date of Patent: July 13, 2010
    Assignee: Japan Science And Technology Agency
    Inventors: Tsutomu Katsuki, Kazufumi Omura, Tatsuya Uchida, Ryo Irie
  • Publication number: 20100113815
    Abstract: This invention provides a method for producing an optically active aziridine compound or amine compound, which uses as a catalyst a Ru(salen)(CO) complex represented by the following formula (I) or its enantiomer having a high stability, in a high turnover number (TON) and a high enantioselectivity. In the formula (I), Ar is represented by the following formula (VI) or (VII), wherein in the formula (VI), Xs are independently a halogen or a halogenated alkyl group and R1 and R2s are independently hydrogen or an alkyl group or a trialkylsilyl group having a carbon number of 1-4, and in the formula (VII), R3 is a bulky group.
    Type: Application
    Filed: January 5, 2010
    Publication date: May 6, 2010
    Applicant: JAPAN SCIENCE AND TECHNOLOGY AGENCY
    Inventors: Tsutomu Katsuki, Kazufumi Omura, Tatsuya Uchida, Ryo Irie
  • Publication number: 20100113835
    Abstract: This invention provides a method for producing an optically active aziridine compound or amine compound, which uses as a catalyst a Ru(salen)(CO) complex represented by the following formula (I) or its enantiomer having a high stability, in a high turnover number (TON) and a high enantioselectivity. In the formula (I), Ar is represented by the following formula (VI) or (VII), wherein in the formula (VI), Xs are independently a halogen or a halogenated alkyl group and R1 and R2s are independently hydrogen or an alkyl group or a trialkylsilyl group having a carbon number of 1-4, and in the formula (VII), R3 is a bulky group.
    Type: Application
    Filed: January 5, 2010
    Publication date: May 6, 2010
    Applicant: JAPAN SCIENCE AND TECHNOLOGY AGENCY
    Inventors: Tsutomu Katsuki, Kazufumi Omura, Tatsuya Uchida, Ryo Irie
  • Publication number: 20100094037
    Abstract: An optically active sulfoxide compound that is useful as an intermediate for synthesis or an active ingredient of a physiologically active substance such as a pharmaceutical agent is produced at a high optical purity. A process for producing an optically active sulfoxide compound of formula (4) comprises oxidizing a sulfide compound of formula (3) in the presence of an optically active metal complex of formula (1), (1?), (2) or (2?) by using an oxidizing agent. The present invention is also directed to the optically active metal complex.
    Type: Application
    Filed: March 10, 2008
    Publication date: April 15, 2010
    Applicant: NISSAN CHEMICAL INDUSTRIES, LTD.
    Inventors: Tsutomu Katsuki, Hiromichi Egami
  • Publication number: 20090099381
    Abstract: The present invention relates to a production method capable of producing an optically active ?-hydroxyphosphonic acid and its derivatives with sufficiently high enantioselectivity not only for aromatic aldehydes but also for aliphatic aldehydes, and more specifically to a method of producing an optically active ?-hydroxyphosphonic acid and its derivatives, characterized in that an optically active aluminum(salalen) complex represented by any one of the following formulae (I), (I?), (II) and (II?): [wherein R1s are each alkyl group or aryl group independently; R2s are each alkyl group or aryl group independently; R3s are each alkyl group or aryl group independently, and two R3s may bond with each other to form a ring; R4s are each hydrogen atom, halogen atom, alkyl group, alkoxy group, nitro group, or cyano group independently; R5 is alkyl group; and X1 is halogen atom, alkyl group, alkoxy group, acetoxy group or toluenesulfonyloxy group] is used as a catalyst to asymmetrically hydrophosphonylate an aldeh
    Type: Application
    Filed: March 20, 2006
    Publication date: April 16, 2009
    Applicant: JAPAN SCIENCE AND TECHNOLOGY AGENCY
    Inventors: Tsutomu Katsuki, Bunnai Saito
  • Publication number: 20090043100
    Abstract: [Problems] To provide an efficient process for producing an optically active chromene oxide compound which is an important intermediate for a benzopyran compound effective in the treatment of arrhythmia. [Means For Solving Problems] The process for producing an optically active chromene oxide compound comprises using an optically active titanium complex represented by, e.g., the formula (1) or (2) as a catalyst to asymmetrically oxidize an optically active chromene compound with high enantioselectivity in high chemical yield.
    Type: Application
    Filed: March 9, 2007
    Publication date: February 12, 2009
    Applicant: NISSAN CHEMICAL INDUSTRIES, LTD
    Inventors: Shoichi Kondo, Kowichiro Saruhashi, Hisayuki Watanabe, Tsutomu Katsuki
  • Publication number: 20080234502
    Abstract: [Problem] To provide a production method of optically active epoxy compound, and a complex used for the production method and a production method of the complex. [Means for solving the problem] The skeleton that is necessary for expressing a high catalyst activity of optically active titanium salan complex of formulae (1) and (1?) and the substituent that is useful therefor and the position of the substituent are identified, and it is found that optically active epoxy compounds can be produced with a high enantioselectivity and a high chemical yield compared with a case where the prior optically active titanium salan complex is used. The production method comprises subjecting a prochiral compound (formula (4), (5) or (6)) having carbon-carbon double bond in the molecule to asymmetric epoxidation to produce an optically active epoxy compound (formula (7), (8) or (9)). The present invention relates also to a complex used for the production method and a production method of the complex.
    Type: Application
    Filed: November 8, 2007
    Publication date: September 25, 2008
    Applicant: NISSAN CHEMICAL INDUSTRIES, LTD.
    Inventors: Shoichi Kondo, Kazuhiro Matsumoto, Yuji Sawada, Tsutomu Katsuki
  • Publication number: 20080081916
    Abstract: This invention provides a method for producing an optically active aziridine compound or amine compound, which uses as a catalyst a Ru(salen)(CO) complex represented by the following formula (I) or its enantiomer having a high stability, in a high turnover number (TON) and a high enantioselectivity. In the formula (I), Ar is represented by the following formula (VI) or (VII), wherein in the formula (VI), Xs are independently a halogen or a halogenated alkyl group and R1 and R2s are independently hydrogen or an alkyl group or a trialkylsilyl group having a carbon number of 1-4, and in the formula (VII), R3 is a bulky group.
    Type: Application
    Filed: June 16, 2005
    Publication date: April 3, 2008
    Applicant: JAPAN SCIENCE AND TECHNOLOGY AGENCY
    Inventors: Tsutomu Katsuki, Kazufumi Omura, Tatsuya Uchida, Ryo Irie
  • Publication number: 20080071099
    Abstract: There is provided a method for industrially producing optically active epoxy compounds by asymmetrically epoxidizing prochiral unsaturated compounds with an oxidant using as a catalyst a single substance or a di-?-oxo dimer derived therefrom represented by any of the following formulae (I), (I?), (II), (II?), (III), (III?), (IV), and (IV?): [wherein R1s are independently an alkyl group or an aryl group; R2s are independently an alkyl group or an aryl group; R3s are independently an alkyl group or an aryl group, provided that two R3s may be bonded with each other to form a ring; R4s are independently a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a nitro group, or a cyano group; M is TiY2 (Y is Cl, alkoxide, or a ?-oxo ligand)].
    Type: Application
    Filed: December 27, 2005
    Publication date: March 20, 2008
    Applicant: JAPAN SCIENCE AND TECHNOLOGY AGENCY
    Inventors: Tsutomu Katsuki, Kazuhiro Matsumoto, Yuji Sawada
  • Publication number: 20040230077
    Abstract: An optically active sulfimide compound is produced by using a specified Ru(salen)(CO) complex as a catalyst and subjecting a specified alkyl aryl sulfide compound to an asymmetric sulfimidation with a specified azide compound having an easily eliminating group.
    Type: Application
    Filed: February 13, 2004
    Publication date: November 18, 2004
    Applicant: Kyushu University
    Inventors: Tsutomu Katsuki, Yusuke Tamura, Tatsuya Uchida