Patents by Inventor Kouji Yoshikawa

Kouji Yoshikawa 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: 8680328
    Abstract: A process for producing an optically active cyclopropanecarboxylic acid ester compound represented by the formula (4): (wherein R5, R6 and * each represents the same meaning as defined below), comprising reacting a diazoacetic acid ester represented by the formula (2): N2CHCO2R5??(2) (wherein R5 represents an alkyl group having 1 to 15 carbon atoms or the like) with a compound represented by the formula (3): (wherein R6 represents an alkyl group having 1 to 15 carbon atoms or the like), in the presence of an asymmetric copper complex obtained by reacting a copper compound and an optically active salicylideneaminoalcohol compound represented by the formula (1): (wherein R1 represents an alkyl group having 1 to 4 carbon atoms or the like, R2 represents a hydrogen atom or the like, R3 and R4 independently represent a hydrogen atom or the like, and * represents an asymmetric center).
    Type: Grant
    Filed: September 7, 2009
    Date of Patent: March 25, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Katsuhisa Masumoto, Kouji Yoshikawa
  • Patent number: 8461370
    Abstract: A process for producing comprising reacting a 3-formyl-2,2-dimethylcyclopropanecarboxylate and propionitrile in the presence of a base to obtain 3-(2-cyano-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid or its salt.
    Type: Grant
    Filed: April 5, 2010
    Date of Patent: June 11, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Toru Uekawa, Jun Ohshita, Ichiro Komoto, Kouji Yoshikawa
  • Publication number: 20120323034
    Abstract: A method comprising an oximation step of reacting a formylalkenylcyclopropanecarboxylic acid ester represented by the formula (1): (wherein, R1 represents an alkyl group optionally having substituent(s) or halogen atom(s), and R2 represents an alkyl group optionally having substituent(s) or a benzyl group optionally having substituent(s)) and hydroxylamine in a solvent in the presence at least one compound selected from the group consisting of carboxylic acids and carboxylic acid metal salts, to produce a hydroxyiminoalkenylcyclopropanecarboxylic acid ester represented by the formula (3): (wherein, R1 and R2 are as defined above).
    Type: Application
    Filed: February 25, 2011
    Publication date: December 20, 2012
    Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventors: Kouji Yoshikawa, Toshiyuki Kiji, Jun Ohshita, Toshio Somyo, Manabu Kashiwabara, Yoko Miyanaga
  • Patent number: 8263797
    Abstract: A method for producing a cyclopropanecarboxylic acid compound represented by formula (VI) (wherein R denotes the same as below), which comprising reacting a compound represented by formula (V) (wherein R denotes a chain hydrocarbon group having 1 to 10 carbon atoms or the like, and R1 denotes a chain hydrocarbon group having 1 to 10 carbon atoms optionally substituted with a halogen atom or the like) with an alkali metal borohydride compound in the presence of a solvent.
    Type: Grant
    Filed: December 22, 2008
    Date of Patent: September 11, 2012
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Toru Uekawa, Jun Ohshita, Kouji Yoshikawa, Ichiro Komoto
  • Patent number: 8168816
    Abstract: A method for producing a purified formylcyclopropane compound represented by the formula (1) comprising (A) a step of reacting a crude formylcyclopropane compound represented by the formula (1): wherein R1 represents an alkyl group or the like, with an alkali metal hydrogen sulfite to obtain an alkali metal hydroxymethanesulfonate represented by the formula (2): wherein R1 represents the same meaning as defined above and M represents an alkali metal, and (B) a step of reacting an acid, a base or a water-soluble aldehyde with the alkali metal hydroxymethanesulfonate represented by the formula (2) obtained in the above-mentioned step (A) to obtain a purified formylcyclopropane compound represented by the formula (1).
    Type: Grant
    Filed: December 12, 2006
    Date of Patent: May 1, 2012
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kouji Yoshikawa, Ryo Minamida, Makoto Itagaki
  • Patent number: 8158787
    Abstract: A process for producing a trichloropyrimidine compound represented by the formula (2): wherein R represents a hydrogen atom etc., comprising reacting a dihydroxypyrimidine compound represented by the formula (1): wherein R represents the same meaning as above, with sulfuryl chloride and at least one chlorinating agent selected from the group consisting of hydrogen chloride, thionyl chloride, phosgene, phosphorus oxychloride, phosphorus pentachloride and phosphorus trichloride in the presence of an organic base.
    Type: Grant
    Filed: March 26, 2008
    Date of Patent: April 17, 2012
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koichi Nakazawa, Tomonori Yoshiyama, Kouji Yoshikawa
  • Publication number: 20120016150
    Abstract: A process for producing comprising reacting a 3-formyl-2,2-dimethylcyclopropanecarboxylate and propionitrile in the presence of a base to obtain 3-(2-cyano-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid or its salt.
    Type: Application
    Filed: April 5, 2010
    Publication date: January 19, 2012
    Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventors: Toru Uekawa, Jun Ohshita, Ichiro Komoto, Kouji Yoshikawa
  • Patent number: 7985872
    Abstract: A method for producing an olefin compound represented by the formula (2): wherein R1 and R2 are the same or different, and independently represent an alkyl group or the like, with the proviso that R1 and R2 are not hydrogen atoms at the same time, R3 represents an alkyl group or the like, which comprises contacting a palladium catalyst with an ?,?-unsaturated aldehyde compound represented by the formula (1): wherein R1, R2 and R3 are the same as defined above, in the presence of an inorganic base.
    Type: Grant
    Filed: December 12, 2006
    Date of Patent: July 26, 2011
    Assignee: Sumitomo Chemical Company, Limited
    Inventor: Kouji Yoshikawa
  • Publication number: 20110166372
    Abstract: A process for producing an optically active cyclopropanecarboxylic acid ester compound represented by the formula (4): (wherein R5, R6 and * each represents the same meaning as defined below), comprising reacting a diazoacetic acid ester represented by the formula (2): N2CHCO2R5??(2) (wherein R5 represents an alkyl group having 1 to 15 carbon atoms or the like) with a compound represented by the formula (3): (wherein R6 represents an alkyl group having 1 to 15 carbon atoms or the like), in the presence of an asymmetric copper complex obtained by reacting a copper compound and an optically active salicylideneaminoalcohol compound represented by the formula (1): (wherein R1 represents an alkyl group having 1 to 4 carbon atoms or the like, R2 represents a hydrogen atom or the like, R3 and R4 independently represent a hydrogen atom or the like, and * represents an asymmetric center).
    Type: Application
    Filed: September 7, 2009
    Publication date: July 7, 2011
    Inventors: Katsuhisa Masumoto, Kouji Yoshikawa
  • Patent number: 7893294
    Abstract: A process for production of a trans-2,2-dimethyl-3-formylcyclopropanecarboxylic acid ester comprising: (A) a step of obtaining a mixture containing a trans-2,2-dimethyl-3-(hydroxymethyl)cyclopropanecarboxylic acid ester, (B) a step of conducting an oxidation treatment of the mixture obtained in the step (A) to obtain a mixture containing a crude trans-2,2-dimethyl-3-formylcyclopropanecarboxylic acid ester, (C) a step of contacting the mixture obtained in the step (B) with an aqueous alkali metal hydrogen sulfite solution to obtain an alkali metal salt of a trans-2,2-dimethyl-3-[(hydroxy)(sulfo)methyl]cyclopropanecarboxylic acid ester, and (D) a step of contacting the alkali metal salt obtained in the above-mentioned step (C) with a base or the like to obtain a trans-2,2-dimethyl-3-formylcyclopropanecarboxylic acid ester.
    Type: Grant
    Filed: August 13, 2007
    Date of Patent: February 22, 2011
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Makoto Itagaki, Ryo Minamida, Kouji Yoshikawa
  • Publication number: 20100305353
    Abstract: A method for producing a purified formylcyclopropane compound represented by the formula (1) comprising (A) a step of reacting a crude formylcyclopropane compound represented by the formula (1): wherein R1 represents an alkyl group or the like, with an alkali metal hydrogen sulfite to obtain an alkali metal hydroxymethanesulfonate represented by the formula (2): wherein R1 represents the same meaning as defined above and M represents an alkali metal, and (B) a step of reacting an acid, a base or a water-soluble aldehyde with the alkali metal hydroxymethanesulfonate represented by the formula (2) obtained in the above-mentioned step (A) to obtain a purified formylcyclopropane compound represented by the formula (1).
    Type: Application
    Filed: December 12, 2006
    Publication date: December 2, 2010
    Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventors: Kouji Yoshikawa, Ryo Minamida, Makoto Itagaki
  • Publication number: 20100280267
    Abstract: A method for producing a cyclopropanecarboxylic acid compound represented by formula (VI) (wherein R denotes the same as below), which comprising reacting a compound represented by formula (V) (wherein R denotes a chain hydrocarbon group having 1 to 10 carbon atoms or the like, and R1 denotes a chain hydrocarbon group having 1 to 10 carbon atoms optionally substituted with a halogen atom or the like) with an alkali metal borohydride compound in the presence of a solvent.
    Type: Application
    Filed: December 22, 2008
    Publication date: November 4, 2010
    Inventors: Toru Uekawa, Jun Ohshita, Kouji Yoshikawa, Ichiro Komoto
  • Publication number: 20100160630
    Abstract: A process for producing a trichloropyrimidine compound represented by the formula (2): wherein R represents a hydrogen atom etc., comprising reacting a dihydroxypyrimidine compound represented by the formula (1): wherein R represents the same meaning as above, with sulfuryl chloride and at least one chlorinating agent selected from the group consisting of hydrogen chloride, thionyl chloride, phosgene, phosphorus oxychloride, phosphorus pentachloride and phosphorus trichloride in the presence of an organic base.
    Type: Application
    Filed: March 26, 2008
    Publication date: June 24, 2010
    Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventors: Koichi Nakazawa, Tomonori Yoshiyama, Kouji Yoshikawa
  • Patent number: 7700799
    Abstract: A method for producing a (2-formyl-1-alkenyl)cyclopropane compound represented by the formula (1): wherein R1 and R2 are the same or different, and independently represent a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted aryl group or an optionally substituted aralkyl group, which comprises reacting a formylcyclopropane compound represented by the formula (3): wherein R1 is the same as defined above, with an aldehyde compound represented by the formula (4): wherein R2 is the same as defined above, in the presence of a base.
    Type: Grant
    Filed: January 22, 2009
    Date of Patent: April 20, 2010
    Assignee: Sumitomo Chemical Company, Limited
    Inventor: Kouji Yoshikawa
  • Publication number: 20090314987
    Abstract: A process for production of a trans-2,2-dimethyl-3-formylcyclopropanecarboxylic acid ester comprising: (A) a step of obtaining a mixture containing a trans-2,2-dimethyl-3-(hydroxymethyl)cyclopropanecarboxylic acid ester, (B) a step of conducting an oxidation treatment of the mixture obtained in the step (A) to obtain a mixture containing a crude trans-2,2-dimethyl-3-formylcyclopropanecarboxylic acid ester, (C) a step of contacting the mixture obtained in the step (B) with an aqueous alkali metal hydrogen sulfite solution to obtain an alkali metal salt of a trans-2,2-dimethyl-3-[(hydroxy)(sulfo)methyl]cyclopropanecarboxylic acid ester, and (D) a step of contacting the alkali metal salt obtained in the above-mentioned step (C) with a base or the like to obtain a trans-2,2-dimethyl-3-formylcyclopropanecarboxylic acid ester.
    Type: Application
    Filed: August 13, 2007
    Publication date: December 24, 2009
    Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventors: Makoto Itagaki, Ryo Minamida, Kouji Yoshikawa
  • Publication number: 20090137839
    Abstract: A method for producing a (2-formyl-1-alkenyl)cyclopropane compound represented by the formula (1): wherein R1 and R2 are the same or different, and independently represent a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted aryl group or an optionally substituted aralkyl group, which comprises reacting a formylcyclopropane compound represented by the formula (3): wherein R1 is the same as defined above, with an aldehyde compound represented by the formula (4): wherein R2 is the same as defined above, in the presence of a base.
    Type: Application
    Filed: January 22, 2009
    Publication date: May 28, 2009
    Applicant: Sumitomo Chemical Company, Ltd.
    Inventor: Kouji YOSHIKAWA
  • Publication number: 20090036620
    Abstract: A method for producing an olefin compound represented by the formula (2): wherein R1 and R2 are the same or different, and independently represent an alkyl group or the like, with the proviso that R1 and R2 are not hydrogen atoms at the same time, R3 represents an alkyl group or the like, which comprises contacting a palladium catalyst with an ?,?-unsaturated aldehyde compound represented by the formula (1): wherein R1, R2 and R3 are the same as defined above, in the presence of an inorganic base.
    Type: Application
    Filed: December 12, 2006
    Publication date: February 5, 2009
    Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventor: Kouji Yoshikawa
  • Patent number: 7262320
    Abstract: A process for the production of a 3,3-dimethyl-2-formylcyclopropanecarboxylic acid derivative of formula (2): wherein R is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted aralkyl, which process comprises reacting a 3,3-dimethyl-2-(2-methyl-1-propenyl)cyclopropanecarboxylic acid compound of formula (1): wherein R is as defined above, with a periodic acid compound in the presence of a ruthenium compound.
    Type: Grant
    Filed: December 26, 2002
    Date of Patent: August 28, 2007
    Assignee: Sumitomo Chemical Company, Limited
    Inventor: Kouji Yoshikawa
  • Patent number: 7179439
    Abstract: It is provided that a method for preparing disodium paraperiodate, characterized in that a pH of a reaction mixture which is obtained by reacting sodium iodate, iodic acid or a mixture thereof with sodium hypochlorite using sodium hydroxide is adjusted to the range between 5 and 10.
    Type: Grant
    Filed: March 19, 2003
    Date of Patent: February 20, 2007
    Assignee: Sumitomo Chemical Company, Limited
    Inventor: Kouji Yoshikawa
  • Publication number: 20050090685
    Abstract: A process for the production of a 3,3-dimethyl-2-formylcyclopropanecarboxylic acid derivative of formula (2): wherein R is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted aralkyl, which process comprises reacting a 3,3-dimethyl-2-(2-methyl-1-propenyl)cyclopropanecarboxylic acid compound of formula (1): wherein R is as defined above, with a periodic acid compound in the presence of a ruthenium compound.
    Type: Application
    Filed: December 26, 2002
    Publication date: April 28, 2005
    Inventor: Kouji Yoshikawa