Patents Assigned to Yuki Gosei Kogyo Co., Ltd.
  • Patent number: 11827603
    Abstract: The object of the present invention is to provide 1-(1-tert-butoxycarbonyl-4-piperidylacetyl)-4-mesyloxypiperidine having a low content of impurities The object can be solved by a method for preparing 1-(1-benzyl-4-piperidylacetyl)-4-hydroxypiperidine, comprising the steps of: (1) reductively reacting 1-benzyl-4-piperidylidene acetic acid ethyl ester represented by the formula [1]: to obtain 1-benzyl-4-piperidyl acetic acid ethyl ester represented by the formula [2]: (2) adding an ammonium chloride aqueous solution and an organic solvent to the liquid containing 1-benzyl-4-piperidyl acetic acid ethyl ester, mixing the whole, and separating into an organic layer and an aqueous layer, (3) collecting 1-benzyl-4-piperidyl acetic acid ethyl ester from the organic layer, and (4) reacting the obtained 1-benzyl-4-piperidyl acetic acid ethyl ester with 4-hydroxypiperidine represented by the formula [3]: in the presence of base, to obtain 1-(1-benzyl-4-piperidylacetyl)-4-hydroxypiperidine repr
    Type: Grant
    Filed: January 18, 2019
    Date of Patent: November 28, 2023
    Assignee: YUKI GOSEI KOGYO CO., LTD.
    Inventors: Kiyono Nakagawa, Yoshihiro Ito, Hirohisa Kitahara
  • Publication number: 20230310355
    Abstract: The object of the present invention is to provide an inexpensive and effective sirtuin activator derived from natural products. The problem can be solved by a sirtuin activator comprising ?-alanine or a salt thereof, or a composition for activating sirtuin comprising the sirtuin activator as an active ingredient, of the present invention.
    Type: Application
    Filed: August 18, 2021
    Publication date: October 5, 2023
    Applicants: Yuki Gosei Kogyo Co., Ltd., Kyushu University, National University Corporation
    Inventors: Tetsuji NODA, Tomotsune ONAGA, Yoshinori KATAKURA
  • Publication number: 20220388959
    Abstract: The object of the present invention is to provide 1-(1-tert-butoxycarbonyl piperidylacetyl)-4-mesyloxypiperidine having a low content of impurities The object can be solved by a method for preparing 1-(1-benzyl piperidylacetyl)-4-hydroxypiperidine, comprising the steps of: (1) reductively reacting 1-benzyl-4-piperidylidene acetic acid ethyl ester represented by the formula [1]: to obtain 1-benzyl-4-piperidyl acetic acid ethyl ester represented by the formula [2]: (2) adding an ammonium chloride aqueous solution and an organic solvent to the liquid containing 1-benzyl-4-piperidyl acetic acid ethyl ester, mixing the whole, and separating into an organic layer and an aqueous layer, (3) collecting 1-benzyl-4-piperidyl acetic acid ethyl ester from the organic layer, and (4) reacting the obtained 1-benzyl-4-piperidyl acetic acid ethyl ester with 4-hydroxypiperidine represented by the formula [3]: in the presence of base, to obtain 1-(1-benzyl-4-piperidylacetyl)-4-hydroxypiperidine represented by the for
    Type: Application
    Filed: January 18, 2019
    Publication date: December 8, 2022
    Applicant: YUKI GOSEI KOGYO CO., LTD.
    Inventors: Kiyono NAKAGAWA, Yoshihiro ITO, Hirohisa KITAHARA
  • Publication number: 20220313639
    Abstract: The object of the present invention is to provide a pharmaceutical agent which activate mitochondrial function, particularly, an inexpensive pharmaceutical agent. The problem can be solved by a mitochondrial function activator of the present invention, comprising ?-alanine or glycine, or a salt thereof.
    Type: Application
    Filed: June 16, 2020
    Publication date: October 6, 2022
    Applicants: Yuki Gosei Kogyo Co., Ltd., Kyushu University, National University Corporation
    Inventors: Tetsuji NODA, Tomotsune ONAGA, Yoshinori KATAKURA
  • Patent number: 11332458
    Abstract: The object of the present invention is to provide a simple method for preparing an N-alkoxycarbonyl piperidine derivative. The object can be solved by a method for preparing a hydroxypiperidine derivative, comprising a step of: (A) reacting a piperidylidene acetic acid derivative represented by the formula (1): wherein R1 is an aralkyl group which may have a substituent group, and R2 is an alkyl group, with 4-hydroxypiperidine in the presence of base, to obtain a hydroxypiperidine derivative represented by the formula (2) or the formula (3): wherein R1 is an aralkyl group which may have a substituent group.
    Type: Grant
    Filed: January 18, 2019
    Date of Patent: May 17, 2022
    Assignee: YUKI GOSEI KOGYO CO., LTD.
    Inventors: Kiyono Nakagawa, Yoshihiro Ito, Yumiko Tanaka
  • Publication number: 20210122729
    Abstract: The object of the present invention is to provide a simple method for preparing an N-alkoxycarbonyl piperidine derivative. The object can be solved by a method for preparing a hydroxypiperidine derivative, comprising a step of: (A) reacting a piperidylidene acetic acid derivative represented by the formula (1): wherein R1 is an aralkyl group which may have a substituent group, and R2 is an alkyl group, with 4-hydroxypiperidine in the presence of base, to obtain a hydroxypiperidine derivative represented by the formula (2) or the formula (3): wherein R1 is an aralkyl group which may have a substituent group.
    Type: Application
    Filed: January 18, 2019
    Publication date: April 29, 2021
    Applicant: YUKI GOSEI KOGYO CO., LTD.
    Inventors: Kiyono NAKAGAWA, Yoshihiro ITO, Yumiko TANAKA
  • Publication number: 20200205449
    Abstract: The present disclosure relates to a hardening inhibitor of brine-containing noodles or a brine-containing wonton wrapper including an ?-amino acid, a ?-amino acid, or a ?-amino acid, or a salt thereof.
    Type: Application
    Filed: May 24, 2018
    Publication date: July 2, 2020
    Applicant: YUKI GOSEI KOGYO CO., LTD.
    Inventors: Yuki KAMINAGA, Tetsuji NODA, Toshiya ISHII, Tetsuya KOBAYASHI
  • Patent number: 10526288
    Abstract: The object of the present invention is to provide a method for preparing 4-(piperidin-4-yl)morpholine, which is easy to operate. The object can be solved by a method for preparing 4-(1-benzylpiperidin-4-yl)morpholine, characterized in that 5-fold molar or more of morpholine is added to 1-benzyl-4-piperidone, and the mixture is reacted with hydrogen under 1 MPa or less in the presence of platinum catalyst or palladium catalyst.
    Type: Grant
    Filed: June 9, 2017
    Date of Patent: January 7, 2020
    Assignee: YUKI GOSEI KOGYO CO., LTD.
    Inventors: Hiromi Ishikawa, Kiyono Nakagawa, Yukiko Takeda
  • Patent number: 10370369
    Abstract: A novel acid addition salt of 3-aminoquinuclidine, which is an industrially useful compound as an intermediate of medicines and does not exhibit deliquescence, is provided. In particular, an acid addition salt of 3-aminoquinuclidine selected from the group consisting of racemic 3-aminoquinuclidine, (R)-3-aminoquinuclidine, and (S)-3-aminoquinuclidine, and acid selected from the group consisting of phosphoric acid, sulfuric acid, fumaric acid, terephthalic acid, oxalic acid, p-toluenesulfonic acid, (±)-10-camphorsulfonic acid, and (?)-10-camphorsulfonic acid, is provided.
    Type: Grant
    Filed: March 31, 2016
    Date of Patent: August 6, 2019
    Assignee: YUKI GOSEI KOGYO CO. LTD.
    Inventors: Yukiko Takeda, Tetsuji Noda
  • Publication number: 20190210968
    Abstract: The object of the present invention is to provide a method for preparing 4-(piperidin-4-yl)morpholine, which is easy to operate. The object can be solved by a method for preparing 4-(1-benzylpiperidin-4-yl)morpholine, characterized in that 5-fold molar or more of morpholine is added to 1-benzyl-4-piperidone, and the mixture is reacted with hydrogen under 1 MPa or less in the presence of platinum catalyst or palladium catalyst.
    Type: Application
    Filed: June 9, 2017
    Publication date: July 11, 2019
    Applicant: YUKI GOSEI KOGYO CO., LTD.
    Inventors: Hiromi ISHIKAWA, Kiyono NAKAGAWA, Yukiko TAKEDA
  • Publication number: 20180118736
    Abstract: A novel acid addition salt of 3-aminoquinuclidine, which is an industrially useful compound as an intermediate of medicines and does not exhibit deliquescence, is provided. In particular, an acid addition salt of 3-aminoquinuclidine selected from the group consisting of racemic 3-aminoquinuclidine, (R)-3-aminoquinuclidine, and (S)-3-aminoquinuclidine, and acid selected from the group consisting of phosphoric acid, sulfuric acid, fumaric acid, terephthalic acid, oxalic acid, p-toluenesulfonic acid, (±)-10-camphorsulfonic acid, and (?)-10-camphorsulfonic acid, is provided.
    Type: Application
    Filed: March 31, 2016
    Publication date: May 3, 2018
    Applicant: YUKI GOSEI KOGYO CO. LTD.
    Inventors: Yukiko TAKEDA, Tetsuji NODA
  • Patent number: 8227234
    Abstract: A process for preparing a 2-hydroxy-4-substituted pyridine compound using a microbiological method, a novel microorganism, and a novel compound are provided.
    Type: Grant
    Filed: August 11, 2010
    Date of Patent: July 24, 2012
    Assignee: Yuki Gosei Kogyo Co., Ltd.
    Inventors: Mie Sasaki, Seiichiro Matsumoto
  • Patent number: 8227617
    Abstract: A process for preparing a 2-hydroxy-4-substituted pyridine compound using a microbiological method, a novel microorganism, and a novel compound are provided.
    Type: Grant
    Filed: August 11, 2010
    Date of Patent: July 24, 2012
    Assignee: Yuki Gosei Kogyo Co., Ltd.
    Inventors: Mie Sasaki, Seiichiro Matsumoto
  • Patent number: 7927843
    Abstract: The present invention discloses a method of preparing 2-deoxyribose 5-phosphate by reacting glyceraldehyde 3-phosphate and acetaldehyde in the presence of either a microorganism itself which contains 2-deoxyribose-5-phosphate aldolase but substantially no phosphates or the enzyme derived from the microorganism. The present invention also discloses a method of preparing 2-deoxyribose 5-phosphate by reacting dihydroxyacetone phosphate and acetaldehyde in the presence of either a microorganism itself which contains 2-deoxyribose-5-phosphate aldolase and triose-phosphate isomerase but substantially no phosphates or the enzymes derived from the microorganism.
    Type: Grant
    Filed: July 25, 2007
    Date of Patent: April 19, 2011
    Assignees: Yuki Gosei Kogyo Co., Ltd., Novartis AG
    Inventors: Sakayu Shimizu, Jun Ogawa
  • Patent number: 7927842
    Abstract: The present invention discloses a method of preparing 2-deoxyribose 5-phosphate by reacting glyceraldehyde 3-phosphate and acetaldehyde in the presence of either a microorganism itself which contains 2-deoxyribose-5-phosphate aldolase but substantially no phosphatase or the enzyme derived from the microorganism. The present invention also discloses a method of preparing 2-deoxyribose 5-phosphate by reacting dihydroxyacetone phosphate and acetaldehyde in the presence of either a microorganism itself which contains 2-deoxyribose-5-phosphate aldolase and triose-phosphate isomerase but substantially no phosphatase or the enzymes derived from the microorganism.
    Type: Grant
    Filed: July 25, 2007
    Date of Patent: April 19, 2011
    Assignees: Yuki Gosei Kogyo Co. Ltd., Novartis AG
    Inventors: Sakayu Shimizu, Jun Ogawa
  • Patent number: 7803585
    Abstract: A process for preparing a 2-hydroxy-4-substituted pyridine compound using a microbiological method, a novel microorganism, and a novel compound are provided.
    Type: Grant
    Filed: September 16, 2005
    Date of Patent: September 28, 2010
    Assignee: Yuki Gosei Kogyo Co., Ltd.
    Inventors: Mie Sasaki, Seiichiro Matsumoto
  • Patent number: 7270992
    Abstract: The present invention discloses a method of preparing 2-deoxyribose 5-phosphate by reacting glyceraldehyde 3-phosphate and acetaldehyde in the presence of either a microorganism itself which contains 2-deoxyribose-5-phosphate aldolase but substantially no phosphatase or the enzyme derived from the microorganism. The present invention also discloses a method of preparing 2-deoxyribose 5-phosphate by reacting dihydroxyacetone phosphate and acetaldehyde in the presence of either a microorganism itself which contains 2-deoxyribose-5-phosphate aldolase and triose-phosphate isomerase but substantially no phosphatase or the enzymes derived from the microorganism.
    Type: Grant
    Filed: September 2, 2003
    Date of Patent: September 18, 2007
    Assignees: Novartis AG, Yuki Gosei Kogyo Co., Ltd.
    Inventors: Sakayu Shimizu, Jun Ogawa
  • Patent number: 7148042
    Abstract: A glyoxal-guanosine-group compound is prepared either by reacting glyoxal-guanine with any one of ribose-1-phosphate and 2-deoxyribose-1-phosphate in the presence of purine nucleoside phosphorylase, or by reacting glyoxal-guanine with any one selected from the group consisting of uridine, 2?-deoxyuridine and thymidine, together with phosphate ion, in the presence of purine nucleoside phosphorylase and pyrimidine nucleoside phosphorylase. The glyoxal-guanosine-group compound is then decomposed by alkali, whereby a guanosine-group compound consisting of guanosine and 2?-deoxyguanosine is prepared.
    Type: Grant
    Filed: July 8, 2003
    Date of Patent: December 12, 2006
    Assignee: Yuki Gosei Kogyo Co., Ltd.
    Inventors: Yoichi Mikami, Seiichiro Matsumoto, Yoshinori Hayashi, Toyoki Sato
  • Patent number: 7141396
    Abstract: A glyoxal-guanosine-group compound is prepared either by reacting glyoxal-guanine with any one of ribose-1-phosphate and 2-deoxyribose-1-phosphate in the presence of purine nucleoside phosphorylase, or by reacting glyoxal-guanine with any one selected from the group consisting of uridine, 2?-deoxyuridine and thymidine, together with phosphate ion, in the presence of purine nucleoside phosphorylase and pyrimidine nucleoside phosphorylase. The glyoxal-guanosine-group compound is then decomposed by alkali, whereby a guanosine-group compound consisting of guanosine and 2?-deoxyguanosine is prepared.
    Type: Grant
    Filed: July 8, 2003
    Date of Patent: November 28, 2006
    Assignee: Yuki Gosei Kogyo Co., Ltd.
    Inventors: Yoichi Mikami, Seiichiro Matsumoto, Yoshinori Hayashi, Toyoki Sato
  • Patent number: 7141397
    Abstract: A glyoxal-guanosine-group compound is prepared either by reacting glyoxal-guanine with any one of ribose-1-phosphate and 2-deoxyribose-1-phosphate in the presence of purine nucleoside phosphorylase, or by reacting glyoxal-guanine with any one selected from the group consisting of uridine, 2?-deoxyuridine and thymidine, together with phosphate ion, in the presence of purine nucleoside phosphorylase and pyrimidine nucleoside phosphorylase. The glyoxal-guanosine-group compound is then decomposed by alkali, whereby a guanosine-group compound consisting of guanosine and 2?-deoxyguanosine is prepared.
    Type: Grant
    Filed: July 8, 2003
    Date of Patent: November 28, 2006
    Assignee: Yuki Gosei Kogyo Co., Ltd.
    Inventors: Yoichi Mikami, Seiichiro Matsumoto, Yoshinori Hayashi, Toyoki Sato