Patents by Inventor Yutaka Kameyama
Yutaka Kameyama 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: 6399770Abstract: A process for preparing a &bgr;-hydroxyester comprising reducing a &bgr;-keto ester in the presence of a salt of ammonium borohydride.Type: GrantFiled: June 6, 2000Date of Patent: June 4, 2002Assignee: Otsuka Kagaku Kabushiki KaishaInventor: Yutaka Kameyama
-
Patent number: 6339152Abstract: The present invention is directed to a process for preparing an exo-methylenepenam compound wherein a cephem compound 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 cephem compound and with a metal compound having a higher standard oxidation reduction potential than the metal and in an amount of 0.Type: GrantFiled: September 7, 1999Date of Patent: January 15, 2002Assignee: Otsuka Kagaku Kabushiki KaishaInventors: Sigeru Torii, Hideo Tanaka, Yutaka Kameyama, Yoshihisa Tokumaru
-
Patent number: 6197185Abstract: 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: GrantFiled: December 10, 1999Date of Patent: March 6, 2001Assignee: Otsuka Kagaku Kabushiki KaishaInventors: Sigeru Torii, Hideo Tanaka, Michio Sasaoka, Yutaka Kameyama
-
Patent number: 6150519Abstract: 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: GrantFiled: March 11, 1999Date of Patent: November 21, 2000Assignee: Otsuka Kagaku Kabushiki KaishaInventors: Sigeru Torii, Hideo Tanaka, Michio Sasaoka, Yutaka Kameyama, Isao Wada, Yasuhisa Amano
-
Patent number: 6043356Abstract: 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: GrantFiled: January 20, 1999Date of Patent: March 28, 2000Assignee: Otsuka Kagaku Kabushiki KaishaInventors: Sigeru Torii, Hideo Tanaka, Michio Sasaoka, Yutaka Kameyama
-
Patent number: 6011151Abstract: 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: GrantFiled: November 6, 1996Date of Patent: January 4, 2000Assignee: Otsuka Kagaku Kabushiki KaishaInventors: Sigeru Torii, Hideo Tanaka, Michio Sasaoka, Yutaka Kameyama, Daisuke Suzuki
-
Patent number: 5986091Abstract: 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: GrantFiled: November 12, 1997Date of Patent: November 16, 1999Assignee: Otsuka Kagaku Kabushiki KaishaInventors: Sigeru Torii, Hideo Tanaka, Michio Sasaoka, Yutaka Kameyama
-
Patent number: 5977352Abstract: 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: GrantFiled: February 6, 1998Date of Patent: November 2, 1999Assignee: Otsuka Kagaku Kabushiki KaishaInventors: Michio Sasaoka, Sigeru Torii, Hideo Tanaka, Ryo Kikuchi, Yutaka Kameyama
-
Patent number: 5968335Abstract: 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: GrantFiled: November 7, 1997Date of Patent: October 19, 1999Assignee: Otsuka Kagaku Kabushiki KaishaInventors: Sigeru Torii, Hideo Tanaka, Michio Sasaoka, Yutaka Kameyama
-
Patent number: 5929233Abstract: 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: GrantFiled: November 6, 1996Date of Patent: July 27, 1999Assignee: Otsuka Kagaku Kabushiki KaishaInventors: Sigeru Torii, Hideo Tanaka, Michio Sasaoka, Yutaka Kameyama, Isao Wada, Yasuhisa Amano
-
Patent number: 5919924Abstract: 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: GrantFiled: June 3, 1997Date of Patent: July 6, 1999Assignee: Otsuka Kagaku Kabushiki KaishaInventors: Michio Sasaoka, Shigeru Torii, Hideo Tanaka, Ryo Kikuchi, Yutaka Kameyama, Kouichi Sorajo
-
Patent number: 5905147Abstract: 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: GrantFiled: November 6, 1996Date of Patent: May 18, 1999Assignee: Otsuka Kagaku Kabushiki KaishaInventors: Sigeru Torii, Hideo Tanaka, Michio Sasaoka, Yutaka Kameyama
-
Patent number: 5693792Abstract: The object of the invention is to provide a .beta.-lactam compound and a 2-substituted methyl-3-cephem compound, both of which are of value as intermediates for the synthesis of cephem antibiotics.The .beta.-lactam compound of the invention may be represented by the general formula ##STR1## wherein R.sup.1 represents a protected amino group, for instance; R.sup.2 represents hydrogen, for instance; R.sup.3 represents hydrogen or a carboxy-protecting group; R.sup.4 represents an aryl group which may be substituted; R.sup.5 represents an alkenyl group which may be substituted, for instance. The 2-substituted methyl-3-cephem compound of the invention may be represented by the general formula ##STR2## wherein R.sup.1, R.sup.2 and R.sup.3 are as defined above; R.sup.6 represents an aryl group which may be substituted.Type: GrantFiled: August 15, 1995Date of Patent: December 2, 1997Assignee: Otsuga Kagaku Kabushiki KaishaInventors: Shigeru Torii, Hideo Tanaka, Mitio Sasaoka, Takashi Shiroi, Yutaka Kameyama
-
Patent number: 5656754Abstract: 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: GrantFiled: March 22, 1994Date of Patent: August 12, 1997Assignee: Otsuka Kagaku Kabushiki KaishaInventors: Shigeru Torii, Hideo Tanaka, Michio Sasaoka, Takashi Shiroi, Yutaka Kameyama
-
Patent number: 5599925Abstract: A penam derivative of the general formula ##STR1## wherein R.sup.1 means hydrogen, halogen, amino or protected amino; R.sup.2 means hydrogen, halogen, lower alkoxy, lower acyl, lower alkyl, hydroxy- or protected hydroxy-substituted lower alkyl, hydroxy or protected hydroxy, or R.sup.1 and R.sup.2 may jointly represent oxo; R.sup.3 means hydrogen or a carboxy-protecting group; R.sup.4 means hydrogen; R.sup.5 means a group of the formula --CH.sub.2 Y where Y means halogen, --N.sub.3, --ONO.sub.2, --OR.sup.6, --OCOR.sup.6, --SCSOR.sup.6, --SCSN(R.sup.6).sub.2, --SR.sup.6, --SO.sub.2 R.sup.6, --NHR.sup.6, --N(R.sup.6).sub.2 or a substituted or unsubstituted nitrogen-containing heterocyclic group having a free valence on nitrogen; R.sup.6 means a lower alkyl, aryl or heterocyclic group which is substituted or unsubstituted; or R.sup.4 and R.sup.5 may jointly represent .dbd.CH.sub.2 ; n means 0, 1 or 2; provided, however, that where R.sup.4 and R.sup.5 jointly represent .dbd.CH.sub.2, n is not equal to 0.Type: GrantFiled: September 30, 1994Date of Patent: February 4, 1997Assignee: Otsuka Kagaku Kabushiki KaishaInventors: Shigeru Torii, Hideo Tanaka, Masatoshi Taniguchi, Mitio Sasaoka, Takashi Shiroi, Yutaka Kameyama
-
Patent number: 5470972Abstract: The object of the invention is to provide a .beta.-lactam compound and a 2-substituted methyl-3-cephem compound, both of which are of value as intermediates for the synthesis of cephem antibiotics.The .beta.-lactam compound of the invention may be represented by the general formula ##STR1## wherein R.sup.1 represents a protected amino group, for instance; R.sup.2 represents hydrogen for instance; R.sup.3 represents hydrogen or a carboxy-protecting group; R.sup.4 represents an aryl group which may be substituted; R.sup.5 represents an alkenyl group which may be substituted, for instance. The 2-substituted methyl-3-cephem compound of the invention may be represented by the general formula ##STR2## wherein R.sup.1, R.sup.2 and R.sup.3 are as defined above; R.sup.6 represents an aryl group which may be substituted.Type: GrantFiled: October 14, 1993Date of Patent: November 28, 1995Assignee: Otsuka Kagaku Kabushiki KaishaInventors: Shigeru Torii, Hideo Tanaka, Mitio Sasaoka, Takashi Shiroi, Yutaka Kameyama
-
Patent number: 5288860Abstract: 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: GrantFiled: January 11, 1993Date of Patent: February 22, 1994Assignee: Otsuka Kagaku Kasbushiki KaishaInventors: Sigeru Torii, Hideo Tanaka, Masatoshi Taniguchi, Michio Sasaoka, Takashi Shiroi, Yutaka Kameyama
-
Patent number: 5206361Abstract: 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: GrantFiled: March 7, 1991Date of Patent: April 27, 1993Assignee: Otsuka Kagaku Kabushiki KaishaInventors: Sigeru Torii, Hideo Tanaka, Masatoshi Taniguchi, Michio Sasaoka, Takashi Shiroi, Yutaka Kameyama
-
Patent number: 5204458Abstract: The present invention provides a process for preparing a cephem derivative characterized in that an allenyl .beta.-lactam compound represented by the formula (1) ##STR1## wherein R.sup.1 is amino or protected amino, R.sup.2 is a hydrogen atom or lower alkoxyl, R.sup.3 is a hydrogen atom or carboxylic acid protecting group and X is the group --SO.sub.2 R.sup.4 or --SR.sup.4, R.sup.4 being substituted or unsubstituted aryl or substituted or unsubstituted nitrogen-containing aromatic heterocyclic group is reacted with a nucleophilic agent to obtain the derivative, the cephem derivative being represented by the formula (2) ##STR2## wherein R.sup.1, R.sup.2 and R.sup.3 are as defined above, and Y is the residue of the nucleophilic agent.Type: GrantFiled: March 10, 1992Date of Patent: April 20, 1993Assignee: Otsuka Kagaku Kabushiki KaishaInventors: Sigeru Torii, Hideo Tanaka, Masatoshi Taniguchi, Michio Sasaoka, Takashi Shiroi, Yutaka Kameyama
-
Patent number: 5196530Abstract: The present invention provides a process for preparing a 2-exo-methylenepenam derivative represented by the formula (2), the process being characterized by reacting an allenyl .beta.-lactum compound represented by the formula (1) with a metallic reducing agent, in which R.sup.1, R.sup.2, R.sup.3 and X are defined in the specification.Type: GrantFiled: March 10, 1992Date of Patent: March 23, 1993Assignee: Otsuka Kagaku Kabushiki KaishaInventors: Sigeru Torii, Hideo Tanaka, Masatoshi Taniguchi, Michio Sasaoka, Takashi Shiroi, Yutaka Kameyama