Patents by Inventor Michio Sasaoka

Michio Sasaoka 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: 6197185
    Abstract: The present invention provides a process for preparing an exo-methylenepenam compound represented by the general formula (5) characterized in that a &bgr;-lactam halide compound represented by the general formula (2) is subjected to an electroreduction process to obtain the exo-methylenepenam compound.
    Type: Grant
    Filed: December 10, 1999
    Date of Patent: March 6, 2001
    Assignee: Otsuka Kagaku Kabushiki Kaisha
    Inventors: Sigeru Torii, Hideo Tanaka, Michio Sasaoka, Yutaka Kameyama
  • Patent number: 6150519
    Abstract: A process for preparing an allenyl .beta.-lactam compound represented by the formula (4), characterized by reacting the hydroxyl group of a .beta.-lactam compound represented by the formula (1) with a reactive functional group derivative of sulfonic acid represented by the formula (2) to convert the compound of the formula (1) to a .beta.-lactam compound represented by the formula (3), thereafter reacting the resulting .beta.-lactam compound with a basic anion exchange resin of the type having a tertiary organic base fixed to the resin and isolating the resulting allenyl .beta.
    Type: Grant
    Filed: March 11, 1999
    Date of Patent: November 21, 2000
    Assignee: Otsuka Kagaku Kabushiki Kaisha
    Inventors: Sigeru Torii, Hideo Tanaka, Michio Sasaoka, Yutaka Kameyama, Isao Wada, Yasuhisa Amano
  • Patent number: 6063918
    Abstract: A process for preparing a 2-isocephem derivative characterized in that a thioacetic acid derivative which itself is basic or a mixture of a base and a thioacetic acid derivative is caused to act on a 2-azetidinyl-3,4-dihalogeno-2-butenoic acid compound represented by the general formula (1) in a water-containing organic solvent to obtain a 3-halomethyl-2-isocephem derivative represented by the general formula (2), and a process for preparing a 2-oxaisocephem derivative characterized in that a base is caused to act on a 2-azetidinyl-3,4-dihalogeno-2-butenoic acid compound represented by the general formula (1) in a water-containing organic solvent to obtain a 3-halomethyl-2-oxaisocephem derivative represented by the general formula (3) ##STR1## wherein R.sup.1 is a hydrogen atom, amino or protected amino, R.sup.2 is a hydrogen atom or lower alkoxyl, R.sup.1 and R.sup.2, when taken together, form a cyclic amino protecting group, R.sup.
    Type: Grant
    Filed: July 7, 1997
    Date of Patent: May 16, 2000
    Assignee: Otsuka Kagaku Kabushiki Kaisha
    Inventors: Michio Sasaoka, Daisuke Suzuki, Delsoo Suh, Yoshihisa Tokumaru
  • Patent number: 6043356
    Abstract: The present invention provides a process for preparing an exo-methylenepenam compound represented by the general formula (5) characterized in that a .beta.-lactam halide compound represented by the general formula (2) is reduced with a metal having a standard oxidation-reduction potential of up to -0.3 (V/SCE) in an amount of at least one mole per mole of the halide compound and with a metal compound having a higher standard oxidation-reduction potential than the metal in an amount of 0.0001 to 10 moles per mole of the halide compound, or is subjected to an electroreduction process to obtain the exo-methylenepenam compound.
    Type: Grant
    Filed: January 20, 1999
    Date of Patent: March 28, 2000
    Assignee: Otsuka Kagaku Kabushiki Kaisha
    Inventors: Sigeru Torii, Hideo Tanaka, Michio Sasaoka, Yutaka Kameyama
  • Patent number: 6011151
    Abstract: A process for preparing a .beta.-lactam halide compound represented by the formula (2) characterized by halogenating the allenyl group of an allenyl .beta.-lactam compound represented by the formula (1) with a cupric halide and a metal halide to obtain the .beta.-lactam halide compound ##STR1## wherein R.sup.1 is a hydrogen atom or amino or protected amino, R.sup.2 is a hydrogen atom, halogen atom, lower alkoxyl, lower acyl, or lower alkyl having a hydroxyl group or protected hydroxyl group as a substituent, R.sup.3 is a hydrogen atom or carboxylic acid protecting group, and R.sup.4 is a hydrocarbon group which may have a substituent, or the group --S--S(O)n-Ar, n being 0 to 2, Ar being aryl which may have a substituent ##STR2## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are the same as defined above, X and Y are each halogen atom.
    Type: Grant
    Filed: November 6, 1996
    Date of Patent: January 4, 2000
    Assignee: Otsuka Kagaku Kabushiki Kaisha
    Inventors: Sigeru Torii, Hideo Tanaka, Michio Sasaoka, Yutaka Kameyama, Daisuke Suzuki
  • Patent number: 5986091
    Abstract: The present invention provides a process for preparing an allenyl .beta.-lactam compound represented by the formula (II) or a process for preparing a 3-halocephem compound of the formula (III) by altering the reaction conditions with use of a .beta.-lactam halide compound represented by the formula (I) serving as the starting material ##STR1## wherein R.sub.1 is a hydrogen atom, amino or protected amino, R.sub.2 is aryl which may have a substituent, n is 0 to 2, R.sub.3 is a hydrogen atom or carboxylic acid protective group, X is a halogen atom, and Y is a halogen atom or a leaving group ##STR2## wherein R.sub.1, R.sub.2, n and R.sub.3 are as defined above ##STR3## wherein R.sub.1, R.sub.3 and X are as defined above.
    Type: Grant
    Filed: November 12, 1997
    Date of Patent: November 16, 1999
    Assignee: Otsuka Kagaku Kabushiki Kaisha
    Inventors: Sigeru Torii, Hideo Tanaka, Michio Sasaoka, Yutaka Kameyama
  • Patent number: 5977352
    Abstract: The present invention provides a process for preparing 3-norcephem compound represented by the formula (2), characterized in that a hydride reagent is acted on a halogenated .beta.-lactam compound represented by the formula (1) in the presence of a cuprous compound ##STR1## wherein R.sub.1 is a hydrogen atom, amino group or protected amino group, R.sub.2 is an aryl or substituted aryl, n is 0 to 2, R.sub.3 is a hydrogen atom or carboxylic acid protective group, X is a halogen atom, and Y is a halogen atom or a leaving group ##STR2## wherein R.sub.1 and R.sub.3 are as defined above.
    Type: Grant
    Filed: February 6, 1998
    Date of Patent: November 2, 1999
    Assignee: Otsuka Kagaku Kabushiki Kaisha
    Inventors: Michio Sasaoka, Sigeru Torii, Hideo Tanaka, Ryo Kikuchi, Yutaka Kameyama
  • Patent number: 5968335
    Abstract: A process for preparing a 3-alkoxymethylcephem compound represented by the formula (II) ##STR1## where R.sub.1 is a hydrogen atom, amino or protected amino, R.sub.3 is a hydrogen atom or carboxylic acid protective group and R.sub.4 is lower alkyl, which process is characterized in that a 3-thiomethylcephem compound represented by the formula (I) ##STR2## where R.sub.1 and R.sub.3 are as defined above and R.sub.2 is aryl which may have a substituent, is electrolytically oxidized in an electrooxidation reaction system in the presence of a lower alcohol using as a positive electrode, a material selected from the group consisting of platinum, tin, aluminum, stainless steel, nickel, lead oxide, carbon, iron oxide and titanium, to obtain the 3-alkoxymethylcephem compound.
    Type: Grant
    Filed: November 7, 1997
    Date of Patent: October 19, 1999
    Assignee: Otsuka Kagaku Kabushiki Kaisha
    Inventors: Sigeru Torii, Hideo Tanaka, Michio Sasaoka, Yutaka Kameyama
  • Patent number: 5929233
    Abstract: The invention provides a process for preparing an allenyl .beta.-lactam of formula (4), by reacting the hydroxyl group of a .beta.-lactam of formula (1) with a reactive derivative of sulfonic acid of formula (2) to convert the compound of formula (1) to a .beta.-lactam of formula (3), thereafter reacting the resulting .beta.-lactam with a basic anion exchange resin of the type having a tertiary organic base fixed to the resin and isolating the allenyl .beta.-lactam of formula (4) with stability and high purity in a high yield.The invention also provides a process for preparing an allenyl .beta.-lactam of formula (4), by reacting the hydroxyl group of a .beta.-lactam compound of formula (1) with a reactive derivative of sulfonic acid of formula (2) to convert the compound of the formula (1) to a .beta.-lactam compound of formula (3), thereafter reacting the resulting .beta.-lactam of formula (3) with a tertiary organic base to convert the compound (3) to the allenyl .beta.
    Type: Grant
    Filed: November 6, 1996
    Date of Patent: July 27, 1999
    Assignee: Otsuka Kagaku Kabushiki Kaisha
    Inventors: Sigeru Torii, Hideo Tanaka, Michio Sasaoka, Yutaka Kameyama, Isao Wada, Yasuhisa Amano
  • Patent number: 5919924
    Abstract: A process for preparing a 3-halogenated cephem derivative represented by the formula (2), characterized by causing a halogenating reagent to act on an allenyl .beta.-lactam compound represented by the formula (1) in the presence of a cuprous salt or cupric salt to obtain the 3-halogenated cephem derivative ##STR1## wherein R.sup.1 is a hydrogen atom, amino or protected amino, R.sup.2 is a hydrogen atom, halogen atom, lower alkoxyl, lower acyl, lower alkyl, lower alkyl having at least one selected from hydroxyl and protected hydroxyl as a substituent, hydroxyl or protected hydroxyl, R.sup.3 is a hydrogen atom or carboxylic acid protecting group, R.sup.4 is an aromatic compound residue which may have a substituent or nitrogen-containing aromatic heterocyclic compound residue which may have a substituent, and n is 0 to 2 ##STR2## wherein R.sup.1, R.sup.2 and R.sup.3 are as defined above, X is a halogen atom.
    Type: Grant
    Filed: June 3, 1997
    Date of Patent: July 6, 1999
    Assignee: Otsuka Kagaku Kabushiki Kaisha
    Inventors: Michio Sasaoka, Shigeru Torii, Hideo Tanaka, Ryo Kikuchi, Yutaka Kameyama, Kouichi Sorajo
  • Patent number: 5905147
    Abstract: The present invention provides a process for producing a .beta.-lactam halide compound represented by the general formula (2) which process is characterized in that the hydroxyl group of a .beta.-lactam halide compound represented by the general formula (1) is substituted with a halogen atom or a leaving group.
    Type: Grant
    Filed: November 6, 1996
    Date of Patent: May 18, 1999
    Assignee: Otsuka Kagaku Kabushiki Kaisha
    Inventors: Sigeru Torii, Hideo Tanaka, Michio Sasaoka, Yutaka Kameyama
  • Patent number: 5770729
    Abstract: The present invention provides an ozonide reducing agent for use in the ozonolysis reaction of an organic compound, the ozonide reducing agent finding wide applications, and being safe and inexpensive from a commercial viewpoint and easy to treat for disposal.The ozonide reducing agent of the invention is a compound wherein sulfur has, at both ends of its molecule, a hydrocarbon residue substituted by a polar functional group.
    Type: Grant
    Filed: January 22, 1996
    Date of Patent: June 23, 1998
    Assignee: Otsuka Kagaku Kabushiki Kaisha
    Inventors: Michio Sasaoka, Daisuke Suzuki, Takashi Shiroi
  • Patent number: 5688942
    Abstract: A process for preparing a 2-isocephem derivative characterized in that a thioacetic acid derivative which itself is basic or a mixture of a base and a thioacetic acid derivative is caused to act on a 2-azetidinyl-3,4-dihalogeno-2-butenoic acid compound represented by the general formula (1) in a water-containing organic solvent to obtain a 3-halomethyl-2-isocephem derivative represented by the general formula (2), and a process for preparing a 2-oxaisocephem derivative characterized in that a base is caused to act on a 2-azetidinyl-3,4-dihalogeno-2-butenoic acid compound represented by the general formula (1) in a water-containing organic solvent to obtain a 3-halomethyl-2-oxaisocephem derivative represented by the general formula (3) ##STR1## wherein R.sup.1 is a hydrogen atom, amino or protected amino, R.sup.2 is a hydrogen atom or lower alkoxyl, R.sup.1 and R.sup.2, when taken together, form a cyclic amino protecting group, R.sup.
    Type: Grant
    Filed: November 6, 1996
    Date of Patent: November 18, 1997
    Assignee: Otsuka Kagaku Kabushiki Kaisha
    Inventors: Michio Sasaoka, Daisuke Suzuki, Delsoo Suh, Yoshihisa Tokumaru
  • Patent number: 5656755
    Abstract: An object of the invention is to provide a process for preparing a 3-substituted cephem compound from an allenyl-.beta.-lactam compound which can be easily produced from an inexpensive penicillin compound by a simple reaction procedure.The process of the invention comprises reacting an allenyl-.beta.-lactam compound with an organohalogen compound in the presence of a metal having a standard oxidation-reduction potential of -0.3 (V/SCE) or less in an amount at least equimolar with the allenyl-.beta.-lactam compound and 0.0001 to 0.5 mole, per mole of the allenyl-.beta.-lactam compound, of a metal compound having a higher standard oxidation-reduction potential than said metal.
    Type: Grant
    Filed: July 6, 1995
    Date of Patent: August 12, 1997
    Assignee: Otsuka Kagaku Kabushiki Kaisha
    Inventors: Shigeru Torii, Hideo Tanaka, Michio Sasaoka, Takashi Shiroi
  • Patent number: 5656754
    Abstract: The present invention provides a process for preparing a cephem compound represented by the general formula (3) characterized in that an allenyl-.beta.-lactam compound represented by the general formula (1) is reacted with an organotin compound represented by the general formula (2) in the presence of a monovalent copper salt ##STR1## wherein R.sup.1 is a hydrogen atom, halogen atom, amino or protected amino, R.sup.2 is a hydrogen atom, halogen atom, lower alkoxyl, lower acyl, lower alkyl, lower alkyl having hydroxyl or protected hydroxyl as a substituent, hydroxyl or protected hydroxyl, or R.sup.1 and R.sup.2 form=0 when taken together, R.sup.3 is a hydrogen atom or carboxylic acid protecting group, R.sup.4 is aryl, aryl having a substituent, nitrogen-containing aromatic heterocyclic group or nitrogen-containing aromatic heterocyclic group having a substituent, and m is 0 or 2,(R.sup.5).sub.n --Sn(R.sup.6).sub.4--n (2)wherein R.sup.
    Type: Grant
    Filed: March 22, 1994
    Date of Patent: August 12, 1997
    Assignee: Otsuka Kagaku Kabushiki Kaisha
    Inventors: Shigeru Torii, Hideo Tanaka, Michio Sasaoka, Takashi Shiroi, Yutaka Kameyama
  • Patent number: 5587464
    Abstract: A process for producing a diazomethane derivative by oxidizing a hydrazone derivative in a two-phase system containing: a) an aqueous solution of a mixture of a caustic alkali and an alkali metal hypochlorite in respective concentrations of 4-14 w/w % and 3-10 w/w % based on the total weight of the solution; b) a hydrophobic organic solvent; c) an inorganic iodine compound, and d) a phase-transfer catalyst.
    Type: Grant
    Filed: August 14, 1995
    Date of Patent: December 24, 1996
    Assignee: Otsuka Kagaku Kabushiki Kaisha
    Inventors: Ichiro Kawahara, Isao Wada, Michio Sasaoka
  • Patent number: 5476913
    Abstract: The present invention provides a polymerizable monomer represented by the general formula (1), polymer thereof, process for preparing the polymer and the use of the polymer ##STR1## wherein R.sup.1 is a hydrogen atom, methyl, chlorine or cyano, R.sup.2 is alkylene having 1 to 4 carbon atoms, R.sup.3 is alkylene having 3 to 10 carbon atoms, R.sup.4 is alkyl having 6 to 18 carbon atoms, R.sup.6 to R.sup.8 are the same or different and are each alkyl or substituted alkyl having 1 to 3 carbon atoms, A is methylene, phenylene, substituted phenylene, --CH.sub.2 O--, --CH.sub.2 CH.sub.2 O--, --CO--, --CO--N(R.sup.9)-- (wherein R.sup.9 is a hydrogen atom or methyl) or vinylene, m is 0 or 1, and X and Y are the same or different, and are each a monovalent anion or form a bivalent anion when taken together.
    Type: Grant
    Filed: July 11, 1994
    Date of Patent: December 19, 1995
    Assignee: Otsuka Kagaku Kabushiki Kaisha
    Inventors: Hiroki Kourai, Michio Sasaoka, Mitsuo Akada, Yoshio Yabuhara, Kouji Mori, Akihiro Murakami, Hiroshi Hama
  • Patent number: 5288860
    Abstract: The present invention provides a thiazolinoazetidinone derivative represented by the formula ##STR1## wherein R.sup.1 is phenyl having or not having substituent(s), methyl having or not having substituent(s) or ##STR2## group, R.sup.3 being phenyl having or not having substituent(s), and R.sup.2 is a hydrogen atom or carboxylic acid protective group, and a process for preparing the same.The present invention further provides a process for preparing a 2-exo-methylenepenam derivative characterized by hydrolyzing the thiazoline ring of a thiazolinoazetidinone derivative of the above formula (1) to effect recyclization and obtain a 2-exo-methylenepenam derivative represented by the formula ##STR3## wherein R.sup.1 and R.sup.2 are as defined above.
    Type: Grant
    Filed: January 11, 1993
    Date of Patent: February 22, 1994
    Assignee: Otsuka Kagaku Kasbushiki Kaisha
    Inventors: Sigeru Torii, Hideo Tanaka, Masatoshi Taniguchi, Michio Sasaoka, Takashi Shiroi, Yutaka Kameyama
  • Patent number: 5247054
    Abstract: An organic polymer ferromagnetic material characterized in that the material comprises a polymer obtained by subjecting to plasma polymerization or oxidation polymerization a methane derivative having two substituents and represented by the formula ##STR1## wherein A is an electron accepting group, and B is an electron donating group, or by copolymerizing the methane derivative with a diarylmethane derivative represented by the formula ##STR2## wherein R.sup.1 is a substituted or unsubstituted phenyl group by plasma polymerization or oxidation polymerization.
    Type: Grant
    Filed: August 1, 1990
    Date of Patent: September 21, 1993
    Assignee: Otsuka Kagaku Kabushiki Kaisha
    Inventors: Hitoshi Tanaka, Tsuneyuki Sato, Todatoshi Ota, deceased, Michio Sasaoka
  • Patent number: 5206361
    Abstract: The present invention provides a thiazolinoazetidinone derivative represented by the formula ##STR1## wherein R.sup.1 is phenyl having or not having substituent(s), methyl having or not having substituent(s) or ##STR2## group, R.sup.3 being phenyl having or not having substituent(s), and R.sup.2 is a hydrogen atom or carboxylic acid protective group, and a process for preparing the same.The present invention further provides a process for preparing a 2-exo-methylenepenam derivative characterized by hydrolyzing the thiazoline ring of a thiazolinoazetidinone derivative of the above formula (1) to effect recyclization and obtain a 2-exo-methylenepenam derivative represented by the formula ##STR3## wherein R.sup.1 and R.sup.2 are as defined above.
    Type: Grant
    Filed: March 7, 1991
    Date of Patent: April 27, 1993
    Assignee: Otsuka Kagaku Kabushiki Kaisha
    Inventors: Sigeru Torii, Hideo Tanaka, Masatoshi Taniguchi, Michio Sasaoka, Takashi Shiroi, Yutaka Kameyama