Patents by Inventor Hidenori Kumobayashi

Hidenori Kumobayashi 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: 6197996
    Abstract: A process for preparing an optically active carnitine ester represented by formula (I): wherein R represents a lower alkyl group; and X represents a halogen atom, is disclosed, comprises asymmetrically hydrogenating a &ggr;-trimethylammonium-3-oxobutanoic ester halide represented by formula (II): wherein R and X are as defined above, in the presence of a ruthenium-optically active phosphine complex as a catalyst. An optically active carnitine ester of any desired isomerism can be obtained through simple operation in high yield at high optical purity. The substrate used is easily available.
    Type: Grant
    Filed: October 22, 1993
    Date of Patent: March 6, 2001
    Assignee: Takasago International Corporation
    Inventors: Takanao Taketomi, Toshiaki Sakaguchi, Hidenori Kumobayashi
  • Patent number: 5859249
    Abstract: Disclosed is a 2-phenyl-2-(2'-piperidinylidene)acetate derivative suitably used for a raw material of a 2-phenyl-2-(2'-piperidinyl)acetate derivative and a process for manufacturing the same. Also disclosed is a process for manufacturing an optically active 2-phenyl-2-(2'-piperidinyl)acetate derivative which is a major intermediate for an antidepressant. The 2-phenyl-2-(2'-piperidinylidene)acetate derivative is manufactured by cyclizing a 7-(N-substituted amino)-3-oxo-2-heptanoate derivative. The optically active 2-phenyl-2-(2'-piperidinyl)acetate derivative is manufactured by asymmetrically hydrogenating the 2-phenyl-2-(2'-piperidinylidene)acetate derivative in the presence of a complex of a Group VIII transition metal or an acid.
    Type: Grant
    Filed: July 16, 1997
    Date of Patent: January 12, 1999
    Assignee: Takasago International Corporation
    Inventors: Nobuo Seido, Takenobu Nishikawa, Tsukasa Sotoguchi, Yoshifumi Yuasa, Takashi Miura, Hidenori Kumobayashi
  • Patent number: 5847222
    Abstract: The present invention provides a ligand for a novel catalyst superior in such characteristics as selectivity (chemoselectivity and enantioselectivity) and catalytic activity in asymmetric synthesis reactions and a ligand for a novel catalyst effective in an asymmetric hydrogenation reaction in particular. The ligand is an optically active diphosphine compound represented by the following formula: ##STR1## where Ph is a phenyl group, X is a chlorine or bromine atom, and R.sup.1 and R.sup.2 are each an alkyl group having 1 to 3 carbon atoms.
    Type: Grant
    Filed: August 26, 1997
    Date of Patent: December 8, 1998
    Assignee: Takasago International Corporation
    Inventors: Tohru Yokozawa, Noboru Sayo, Kazuhiko Matsumura, Hidenori Kumobayashi
  • Patent number: 5837877
    Abstract: A process for preparing optically active 4-hydroxy-2-pyrrolidone comprising asymmetrically hydrogenating an N-substituted-4-amino-3-oxobutanoic ester represented by formula (I): ##STR1## wherein R.sup.1 represents a benzyloxycarbonyl group, the benzene ring of which may be substituted; and R.sup.2 represents a lower alkyl group having 1 to 4 carbon atoms, in the presence of a ruthenium-optically active phosphine complex as a catalyst to obtain an optically active N-substituted-4-amino-3-hydroxybutanoic ester, deblocking, and cyclizing the ester. A series of the reactions can be carried out in one pot.
    Type: Grant
    Filed: January 29, 1997
    Date of Patent: November 17, 1998
    Assignee: Takasago International Corporation
    Inventors: Shigeru Mitsuhashi, Hidenori Kumobayashi
  • Patent number: 5824822
    Abstract: A phosphine-phosphinite compound represented by formula (I): ##STR1## wherein R.sup.1 and R.sup.2, which may be the same or different, each represent a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group, and a process for preparing a 4-?(R)-1'-formylethyl!azetidin-2-one derivative using the compound (I). The compound (I), either in combination, or as a complex, with a transition metal compound, is useful as a catalyst for asymmetric hydroformylation and makes it possible to easily synthesize an important intermediate for carbapenem antibiotics or a precursor thereof at high regioselectivity and diastereo-selectivity.
    Type: Grant
    Filed: July 9, 1996
    Date of Patent: October 20, 1998
    Assignee: Takasago International Corporation
    Inventors: Takao Saito, Akifumi Yoshida, Kazuhiko Matsumura, Takashi Miura, Hidenori Kumobayashi
  • Patent number: 5808162
    Abstract: A novel chiral unsymmetric diphosphine compound of formula (I): ##STR1## wherein Ar.sup.1 and Ar.sup.2, which are different from each other, each represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a pyridyl group, a quinolyl group, an isoquinolyl group, a furfuryl group, a benzofurfuryl group, a thienyl group, or a benzothienyl group, and a transition metal complex containing the diphosphine compound as a ligand. The complex catalyzes various asymmetric synthesis reactions, e.g., asymmetric hydrogenation or asymmetric hydrosilylation, exhibiting excellent performance in selectivity, conversion and catalytic activity, to provide a product of desired absolute configuration at high optical purity and in high yield.
    Type: Grant
    Filed: July 18, 1996
    Date of Patent: September 15, 1998
    Assignee: Takasago International Corporation
    Inventors: Noboru Sayo, Xiaoyong Zhang, Tatsuya Omoto, Tohru Yokozawa, Tetsuro Yamasaki, Hidenori Kumobayashi
  • Patent number: 5801271
    Abstract: Disclosed is a 7-(N-substituted amino)-3-oxo-2-phenylheptanoate derivative, 7-(N-substituted amino)-3-hydroxy-2-phenylheptanoate derivative, and 7-(N-substituted amino)-3-benzenesulfonyloxy-2-phenylheptanoate derivative, which are quite important major intermediates for an antidepressant. The 7-(N-substituted amino)-3-oxo-2-phenylheptanoate derivative can be manufactured by condensing an enolate of phenylacetates with a 5-(N-substituted amino) pentanoate derivative.
    Type: Grant
    Filed: July 16, 1997
    Date of Patent: September 1, 1998
    Assignee: Takasago International Corporation
    Inventors: Nobuo Seido, Takenobu Nishikawa, Tsukasa Sotoguchi, Yoshifumi Yuasa, Takashi Miura, Hidenori Kumobayashi
  • Patent number: 5756760
    Abstract: A 1-substituted-2-diphenylphosphinonaphthalene represented by formula (I): ##STR1## wherein at least one of R.sup.1, R.sup.2, R.sup.3, and R.sup.4, which may be the same or different, represents a lower alkyl group having 1 to 4 carbon atoms which may be substituted with an alkoxy group, a phenyl group or --OR.sup.6 (wherein R.sup.6 represents a hydrogen atom, a lower alkyl group having 1 to 4 carbon atoms or an alcohol-protective group), and the rest of them represent a hydrogen atom; A represents a single bond or a methylene group; and R.sup.5 represents a substituted or unsubstituted phenyl group; and a transition metal complex comprising the 1-substituted-2-diphenylphosphinonaphthalene as a ligand. The transition metal complex is useful as a catalyst in asymmetric synthesis.
    Type: Grant
    Filed: March 7, 1997
    Date of Patent: May 26, 1998
    Assignee: Takasago International Corporation
    Inventors: Sotaro Miyano, Tetsutaro Hattori, Yasuko Komuro, Hidenori Kumobayashi
  • Patent number: 5686616
    Abstract: A novel process for preparing an optically active amine by asymmetric hydrogenation of an imine compound, such as an imine compound prepared by condensing benzylamine and acetophenone, in the presence of a catalytic amount of an iridium-optically active phosphine complex and benzylamine or a benzylamine derivative. The present invention provides an optically active amine of high optical purity.
    Type: Grant
    Filed: March 14, 1996
    Date of Patent: November 11, 1997
    Assignee: Takasago International Corporation
    Inventors: Kazuhide Tani, Tsuneaki Yamagata, Yasutaka Kataoka, Hidenori Kumobayashi
  • Patent number: 5631397
    Abstract: Disclosed herein is a process for producing a (2S,5S)-2,5-diamino-1,6-diphenyl-3-hexanone derivative represented by the formula (1): ##STR1## wherein R.sup.1 means a lower alkylcarbonyl group, a halogen-substituted lower alkylcarbonyl group, an arylcarbonyl group or a lower alkoxycarbonyl group, and R.sup.2 and R.sup.3 are identical with or different from each other and denote individually an aryl group or an alkoxy-substituted aryl group, which comprises subjecting a (2S)-2,5-diamino-1,6-diphenyl-4-hexen-3-one derivative represented by the formula (2): ##STR2## wherein R.sup.1, R.sup.2 and R.sup.3 have the same meaning as defined above, to a hydrogenation reaction in the presence of a transition metal-containing catalyst.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: May 20, 1997
    Assignee: Takasago International Corporation
    Inventors: Tetsuro Yamasaki, Hidenori Kumobayashi, Noboru Sayo, Toshiyuki Murayama, Noboru Sano, Takero Ishizaki
  • Patent number: 5629420
    Abstract: A process for preparing a 4-acyloxyazetidinone or a derivative thereof represented by formula (IV): ##STR1## wherein R.sup.1 represents a hydrogen atom, a lower alkyl group, a hydroxyethyl group, or a protected hydroxyethyl group; R.sup.3 represents an alkyl group having from 1 to 10 carbon atoms which may be substituted with a halogen atom, a cyano group, a lower alkoxy group or a phenyl group, or a substituted or unsubstituted phenyl group, provided that the .alpha.-positioned carbon atom of said alkyl group should not have more than two halogen atoms; and R.sup.4 represents a hydrogen atom, a lower alkyl group, or a lower alkoxycarbonyl group, which is useful as an intermediate for penem antibiotics is disclosed, comprising reacting azetidinone or a derivative thereof represented by formula (II): ##STR2## wherein R.sup.1 is as defined above, and R.sup.2 represents a hydrogen atom, a lower alkyl group, a lower alkoxycarbonyl group, or a carboxyl group, with a carboxylic acid represented by formula (III):R.
    Type: Grant
    Filed: May 8, 1995
    Date of Patent: May 13, 1997
    Assignee: Takasago International Corporation
    Inventors: Takao Saito, Hidenori Kumobayashi, Shunichi Murahashi
  • Patent number: 5606052
    Abstract: A process for preparing a 4-acyloxyazetidinone or a derivative thereof represented by formula (IV): ##STR1## wherein R.sup.1 represents a hydrogen atom, a lower alkyl group, a hydroxyethyl group, or a protected hydroxyethyl group; R.sup.3 represents an alkyl group having from 1 to 10 carbon atoms which may be substituted with a halogen atom, a cyano group, a lower alkoxy group or a phenyl group, or a substituted or unsubstituted phenyl group, provided that the .alpha.-positioned carbon atom of said alkyl group should not have more than two halogen atoms; and R.sup.4 represents a hydrogen atom, a lower alkyl group, or a lower alkoxycarbonyl group, which is useful as an intermediate for penem antibiotics is disclosed, comprising reacting azetidinone or a derivative thereof represented by formula (II): ##STR2## wherein R.sup.1 is as defined above, and R.sup.2 represents a hydrogen atom, a lower alkyl group, a lower alkoxycarbonyl group, or a carboxyl group, with a carboxylic acid represented by formula (III):R.
    Type: Grant
    Filed: May 8, 1995
    Date of Patent: February 25, 1997
    Assignee: Takasago International Corporation
    Inventors: Takao Saito, Hidenori Kumobayashi, Shunichi Murahashi
  • Patent number: 5599954
    Abstract: Compounds represented by the following general structural formula (1) and methods for producing the compounds: ##STR1## R.sup.1 represents a group such as benzyloxycarbonyl, R.sup.2 represents a lower alkyl group, R.sup.3 represents a hydrogen atom or a protecting group, each of M.sup.1 and M.sup.2 represents a metal atom, and n represents the atomic valence of M.sup.1. Intermediates for HMG-CoA reductase inhibitors can be prepared safely and easily from these compounds.
    Type: Grant
    Filed: January 26, 1996
    Date of Patent: February 4, 1997
    Assignee: Takasago International Corporation
    Inventors: Sigeru Mitsuhashi, Tsukasa Sotoguchi, Yoshifumi Yuasa, Hidenori Kumobayashi
  • Patent number: 5581007
    Abstract: A process for preparing an optically active (2S,3S)-allophenylnorstatin derivative (I) is disclosed, comprising asymmetrically hydrogenating a 4-phenyl-2-halogeno-3-oxobutyric ester (III) in the presence of a ruthenium-phosphine complex to obtain a 4-phenyl-(2S)-halogeno-(3R)-hydroxybutyric ester (IV), epoxidizing the ester (IV) in the presence of a base to obtain a 4-phenyl-(2S,3R)-epoxybutyric ester (V), reacting the ester (V) with a tri(lower alkyl)silylazide or a (lower alkyl)diarylsilylazide in the presence of a Lewis to obtain a (3S)-azido-4-phenyl-(2S)-trisubstituted silyloxybutyric ester (VI), hydrogenolyzing the ester (VI) into a (2S,3S)-allophenylnorstatin derivative (VII), protecting the amino group of the compound (VII), and, if desired, hydrolyzing the compound before or after the amino group protection. Compounds (I) can be obtained at high optical purity safely and in good yield.
    Type: Grant
    Filed: March 1, 1996
    Date of Patent: December 3, 1996
    Assignee: Takasago International Corporation
    Inventors: Noboru Sayo, Tetsuro Yamasaki, Hidenori Kumobayashi, Yoshifumi Yuasa, Tsukasa Sotoguchi
  • Patent number: 5563295
    Abstract: A process for the production of an optically active carboxylic acid (I), which comprises subjecting an olefinic carboxylic acid (II) to asymmetric hydrogenation using a complex as a catalyst consisting of an optically active phosphine (III) and a ruthenium compound.Complex of ##STR1## with a ruthenium compound ##STR2## According to the process of the present invention, optically active carboxylic acids can be produced with high yield.
    Type: Grant
    Filed: March 7, 1995
    Date of Patent: October 8, 1996
    Assignee: Takasago International Corporation
    Inventors: Hidemasa Takaya, Xiaoyong Zhang, Kazuhiko Matsumura, Noboru Sayo, Hidenori Kumobayashi
  • Patent number: 5530150
    Abstract: A phosphine compound represented by one of the formulas: ##STR1## wherein R.sup.1 and R.sup.2, which may be the same or different, each represent a phenyl group or a phenyl group substituted with a halogen atom or a lower alkyl group or taken together form a divalent hydrocarbon group; and R.sup.3 and R.sup.4, which may be the same or different, each represent a lower alkyl group, a phenyl group or a phenyl group substituted with a halogen atom, a lower alkyl group or a lower alkoxy group or taken together form a divalent hydrocarbon group, and wherein R.sup.6 and R.sup.6' which may be the same or different, each represent a hydrogen atom, a lower alkyl group or a lower alkoxy group; R.sup.5, R.sup.5', R.sup.11 and R.sup.11' which may be the same or different, each represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a halogen atom; or a pair of R.sup.5 and R.sup.6 or a pair of R.sup.5' and R.sup.6' may form a ring; R.sup.7 and R.sup.
    Type: Grant
    Filed: October 12, 1994
    Date of Patent: June 25, 1996
    Assignee: Takasago International Corporation
    Inventors: Hidemasa Takaya, Nozomu Sakai, Kyoko Tamao, Satoshi Mano, Hidenori Kumobayashi, Tetsuo Tomita, Takao Saito, Kazuhiko Matsumura, Yasushi Kato, Noboru Sayo
  • Patent number: 5523458
    Abstract: Disclosed herein is a process for producing a (2S,5S)-2,5-diamino-1,6-diphenyl-3-hexanone derivative represented by the formula (1): ##STR1## wherein R.sup.1 means a lower alkylcarbonyl group, a halogen-substituted lower alkylcarbonyl group, an arylcarbonyl group or a lower alkoxycarbonyl group, and R.sup.2 and R.sup.3 are identical with or different from each other and denote individually an aryl group or an alkoxy-substituted aryl group, which comprises subjecting a (2S)-2,5-diamino-1,6-diphenyl-4-hexen-3-one derivative represented by the formula (2): ##STR2## wherein R.sup.1, R.sup.2 and R.sup.3 have the same meaning as defined above, to a hydrogenation reaction in the presence of a transition metal-containing catalyst.
    Type: Grant
    Filed: April 19, 1994
    Date of Patent: June 4, 1996
    Assignee: Takasago International Corporation
    Inventors: Tetsuro Yamasaki, Hidenori Kumobayashi, Noboru Sayo, Toshiyuki Murayama, Noboru Sano, Takero Ishizaki
  • Patent number: 5502221
    Abstract: A process for for producing a (2R,3S)-cyclohexylnorstatine or a salt thereof is disclosed, which comprises the steps of: enantioselectively hydrogenating a 4-cyclohexyl-2-halogeno-3-oxobutyric acid ester in the presence of a ruthenium-phosphine complex to produce a 4-cyclohexyl-2-halogeno-(3R)-hydroxybutyric acid ester (2); epoxidizing the compound (2) in the presence of a base to produce a 4-cyclohexyl-(2S,3R)-epoxybutyric acid ester (3); reacting the compound (3) with a lower trialkylsilyl azide in the presence of a Lewis acid to produce a (3S)-azide-4-cyclohexyl-(2S)-substituted butyric acid ester (4); subjecting the compound (4) to hydrogenolysis to produce a (2S,3S)-cyclohexylnorstatine derivative (5); and inverting the configuration at the 2-position of the compound (5).
    Type: Grant
    Filed: May 5, 1995
    Date of Patent: March 26, 1996
    Assignee: Takasago International Corporation
    Inventors: Noboru Sayo, Noboru Sano, Hidenori Kumobayashi
  • Patent number: 5442105
    Abstract: A process for for producing a (2R,3S)-cyclohexylnorstatine or a salt thereof is disclosed, which comprises the steps of: enantioselectively hydrogenating a 4-cyclohexyl-2-halogeno-3-oxobutyric acid ester in the presence of a ruthenium-phosphine complex to produce a 4-cyclohexyl-2-halogeno-(3R)-hydroxybutyric acid ester (2); epoxidizing the compound (2) in the presence of a base to produce a 4-cyclohexyl-(2S,3R)-epoxybutyric acid ester (3); reacting the compound (3) with a lower trialkylsilyl azide in the presence of a Lewis acid to produce a (3S)-azide-4-cyclohexyl-(2S)-substituted butyric acid ester (4); subjecting the compound (4) to hydrogenolysis to produce a (2S,3S)-cyclohexylnorstatine derivative (5); and inverting the configuration at the 2-position of the compound (5).
    Type: Grant
    Filed: December 30, 1993
    Date of Patent: August 15, 1995
    Assignee: Takasago International Corporation
    Inventors: Noboru Sayo, Noboru Sano, Hidenori Kumobayashi
  • Patent number: 5440030
    Abstract: A process for preparing a 4-acyloxyazetidinone or a derivative thereof represented by formula (IV): ##STR1## wherein R.sup.1 represents a hydrogen atom, a lower alkyl group, a hydroxyethyl group, or a protected hydroxyethyl group; R.sup.3 represents an alkyl group having from 1 to 10 carbon atoms which may be substituted with a halogen atom, a cyano group, a lower alkoxy group or a phenyl group, or a substituted or unsubstituted phenyl group, provided that the .alpha.-positioned carbon atom of said alkyl group should not have more than two halogen atoms; and R.sup.4 represents a hydrogen atom, a lower alkyl group, or a lower alkoxycarbonyl group,which is useful as an intermediate for penera antibiotics is disclosed, comprising reacting azetidinone or a derivative thereof represented by formula (II): ##STR2## wherein R.sup.1 is as defined above, and R.sup.2 represents a hydrogen atom, a lower alkyl group, a lower alkoxycarbonyl group, or a carboxyl group,with a carboxylic acid represented by formula (III):R.
    Type: Grant
    Filed: December 16, 1993
    Date of Patent: August 8, 1995
    Assignee: Takasago International Corporation
    Inventors: Takao Saito, Hidenori Kumobayashi, Shunichi Murahashi