Patents by Inventor Kunihiro HIRAI

Kunihiro HIRAI 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).

  • Publication number: 20220010348
    Abstract: A method including obtaining a phosphite form or a phosphorous acid diester form by coupling a nucleoside, nucleotide or oligonucleotide wherein a 5?-hydroxy group is not protected, and other group is optionally protected by a protecting group used for nucleic acid synthesis or bonded to a solid phase carrier, and a nucleoside, nucleotide or oligonucleotide wherein a 3?-hydroxy group or a 3?-amino group is modified by a method for forming a phosphite form or a phosphorous acid diester form, and other group is optionally protected by a protecting group used for nucleic acid synthesis in the presence of an antioxidant is useful for producing an oligonucleotide having a phosphorothioated site.
    Type: Application
    Filed: September 27, 2021
    Publication date: January 13, 2022
    Applicant: AJINOMOTO CO., INC.
    Inventors: Taisuke ICHIMARU, Daisuke TAKAHASHI, Kunihiro HIRAI, Ken YAMASHITA
  • Publication number: 20210371450
    Abstract: A method for producing an oligonucleotide, including a step of removing a temporary protecting group of a 5?-hydroxyl group by adding an acid to a protected oligonucleotide having a phosphorothioate (PS), phosphate (PO) or H-phosphonate moiety, and deacylating a by-product having an acylated 5?-hydroxyl group by solvolysis can complete a condensation reaction to improve a condensation yield, and can markedly reduce impurities such as single base deletion form (N-1mer) and the like.
    Type: Application
    Filed: August 12, 2021
    Publication date: December 2, 2021
    Applicant: AJINOMOTO CO., INC.
    Inventors: Daisuke TAKAHASHI, Taisuke ICHIMARU, Kunihiro HIRAI
  • Patent number: 10919928
    Abstract: Oligonucleotides may be produced by a process, including (1) condensing a nucleoside, nucleotide or oligonucleotide (b), and a nucleoside, nucleotide or oligonucleotide (a), or a substituted nucleotide or oligonucleotide (?) in a non-polar solvent to give a reaction solution containing a phosphite triester product (c); (3) oxidizing or sulfurizing the phosphite triester product (c) to give a reaction solution containing an oligonucleotide (d) wherein the 5?-hydroxy group is protected; (4) deprotecting the oligonucleotide (d) to give a reaction solution containing an oligonucleotide (e) wherein the 5?-hydroxy group is not protected; and (6) adding a polar solvent to the reaction solution containing the oligonucleotide (e) and purifying the oligonucleotide (e) by solid-liquid separation, wherein said nucleoside, nucleotide or oligonucleotide (a) or said substituted nucleotide or oligonucleotide (?) is a compound represented by formula (a-i): wherein Base, Rp1, R10, m, L, Y, and Z are defined herein.
    Type: Grant
    Filed: June 15, 2018
    Date of Patent: February 16, 2021
    Assignee: AJINOMOTO CO., INC.
    Inventors: Kunihiro Hirai, Satoshi Katayama, Naoko Hirose, Taisuke Ichimaru, Ken Yamashita, Daisuke Takahashi
  • Patent number: 10464966
    Abstract: Precipitation promoters, which are an organic compound having one or more linear aliphatic hydrocarbon groups having not less than 10 carbon atoms, wherein the aliphatic hydrocarbon group has not less than 20 carbon atoms in total are useful for precipitating an organic compound protected by an organic group having one or more aliphatic hydrocarbon groups having not less than 10 carbon atoms from a solvent.
    Type: Grant
    Filed: July 20, 2017
    Date of Patent: November 5, 2019
    Assignee: AJINOMOTO CO., INC.
    Inventors: Kunihiro Hirai, Satoshi Katayama, Naoko Hirose, Ken Yamashita, Taisuke Ichimaru, Daisuke Takahashi
  • Publication number: 20180291056
    Abstract: The present invention aims to provide a more stable and efficient method for producing oligonucleotide, particularly, oligonucleotide having various functional groups linked to the 3?-terminal and the like.
    Type: Application
    Filed: June 21, 2018
    Publication date: October 11, 2018
    Applicant: AJINOMOTO CO., INC.
    Inventors: Ken YAMASHITA, Kunihiro Hirai, Satoshi Katayama, Taisuke Ichimaru, Daisuke Takahashi, Naoko Hirose
  • Publication number: 20180282365
    Abstract: Oligonucleotides may be produced by a process, including (1) condensing a nucleoside, nucleotide or oligonucleotide (a) or the like wherein a 5?-hydroxy group is not protected and a nucleoside, nucleotide or oligonucleotide (b) wherein a 5?-hydroxy group is protected in a non-polar solvent to give a reaction solution containing a phosphite triester product (c); (3) oxidizing or sulfurizing the phosphite triester product (c) to give a reaction solution containing an oligonucleotide (d) wherein the 5?-hydroxy group is protected; (4) deprotecting the oligonucleotide (d) to give a reaction solution containing an oligonucleotide (e) wherein the 5?-hydroxy group is not protected; and (6) adding a polar solvent to the reaction solution containing the oligonucleotide (e) and purifying the oligonucleotide (e) by solid-liquid separation or extraction.
    Type: Application
    Filed: June 15, 2018
    Publication date: October 4, 2018
    Applicant: AJINOMOTO CO., INC.
    Inventors: Kunihiro HIRAI, Satoshi Katayama, Naoko Hirose, Taisuke Ichimaru, Ken Yamashita, Daisuke Takahashi
  • Publication number: 20170320904
    Abstract: Precipitation promoters, which are an organic compound having one or more linear aliphatic hydrocarbon groups having not less than 10 carbon atoms, wherein the aliphatic hydrocarbon group has not less than 20 carbon atoms in total are useful for precipitating an organic compound protected by an organic group having one or more aliphatic hydrocarbon groups having not less than 10 carbon atoms from a solvent.
    Type: Application
    Filed: July 20, 2017
    Publication date: November 9, 2017
    Applicant: AJINOMOTO CO., INC.
    Inventors: Kunihiro HIRAI, Satoshi KATAYAMA, Naoko HIROSE, Ken YAMASHITA, Taisuke ICHIMARU, Daisuke TAKAHASHI
  • Patent number: 9371353
    Abstract: The present invention provides a protected nucleotide for elongation, which can be purified efficiently and in a high yield by a liquid-liquid extraction operation, and can achieve an oligonucleotide production method by a phosphoramidite method. It has been found that the above-mentioned problem can be solved by a particular oligonucleotide comprising a protected base and/or particular oligonucleotide protected by a branched chain-containing aromatic group at 3?-position.
    Type: Grant
    Filed: September 19, 2014
    Date of Patent: June 21, 2016
    Assignee: AJINOMOTO CO., INC.
    Inventors: Kunihiro Hirai, Satoshi Katayama, Takayoshi Torii, Ryotaro Nakaya, Daisuke Takahashi
  • Patent number: 9029528
    Abstract: A method of producing an n+p-mer oligonucleotide efficiently in a high yield, which includes use of, as a starting material, an n-mer oligonucleotide wherein the 3?-terminal hydroxyl group is protected, and the 5?-terminal hydroxyl group is protected by a temporary protecting group, and continuously performing, in a solution, (1) a deprotection step of the 5?-terminal hydroxyl group, (2) a 5?-terminal elongation step by the addition of a p-mer oligonucleotide wherein the 3?-position is phosphoramidited, and (3) an oxidation step or a sulfurization step of a phosphite triester moiety.
    Type: Grant
    Filed: May 17, 2012
    Date of Patent: May 12, 2015
    Assignee: Ajinomoto Co., Inc.
    Inventors: Kunihiro Hirai, Satoshi Katayama
  • Publication number: 20150080565
    Abstract: The present invention provides a protected nucleotide for elongation, which can be purified efficiently and in a high yield by a liquid-liquid extraction operation, and can achieve an oligonucleotide production method by a phosphoramidite method. It has been found that the above-mentioned problem can be solved by a particular oligonucleotide comprising a protected base and/or particular oligonucleotide protected by a branched chain-containing aromatic group at 3?-position.
    Type: Application
    Filed: September 19, 2014
    Publication date: March 19, 2015
    Applicant: Ajinomoto Co., Inc.
    Inventors: Kunihiro HIRAI, Satoshi Katayama, Takayoshi Torii, Ryotaro Nakaya, Daisuke Takahashi
  • Patent number: 8846885
    Abstract: The present invention provides a protected nucleotide for elongation, which can be purified efficiently and in a high yield by a liquid-liquid extraction operation, and can achieve an oligonucleotide production method by a phosphoramidite method. It has been found that the above-mentioned problem can be solved by a particular oligonucleotide comprising a protected base and/or particular oligonucleotide protected by a branched chain-containing aromatic group at 3?-position.
    Type: Grant
    Filed: February 15, 2013
    Date of Patent: September 30, 2014
    Assignee: Ajinomoto Co., Inc.
    Inventors: Kunihiro Hirai, Satoshi Katayama, Takayoshi Torii, Ryotaro Nakaya, Daisuke Takahashi
  • Publication number: 20130267697
    Abstract: The present invention provides a protected nucleotide for elongation, which can be purified efficiently and in a high yield by a liquid-liquid extraction operation, and can achieve an oligonucleotide production method by a phosphoramidite method. It has been found that the above-mentioned problem can be solved by a particular oligonucleotide comprising a protected base and/or particular oligonucleotide protected by a branched chain-containing aromatic group at 3?-position.
    Type: Application
    Filed: February 15, 2013
    Publication date: October 10, 2013
    Inventors: Kunihiro Hirai, Satoshi Katayama, Takayoshi Torii, Ryotaro Nakaya, Daisuke Takahashi
  • Publication number: 20120296074
    Abstract: The problem of the present invention is provision of a method of producing an n+p-mer oligonucleotide efficiently in a high yield, which includes use of, as a starting material, an n-mer oligonucleotide wherein the 3?-terminal hydroxyl group is protected, and the 5?-terminal hydroxyl group is protected by a temporary protecting group, and continuously performing, in a solution, (1) a deprotection step of the 5?-terminal hydroxyl group, (2) a 5?-terminal elongation step by the addition of a p-mer oligonucleotide wherein the 3?-position is phosphoramidited, and (3) an oxidation step or a sulfurization step of a phosphite triester moiety. It has been found that the above-mentioned problem can be solved by adding a particular cation scavenger during the deprotection step, applying a neutralization treatment after completion of the deprotection reaction, and using a particular oxidizing agent or sulfurizing agent in the oxidation step or sulfurization step.
    Type: Application
    Filed: May 17, 2012
    Publication date: November 22, 2012
    Applicant: AJINOMOTO CO., INC.
    Inventors: Kunihiro HIRAI, Satoshi KATAYAMA
  • Patent number: D691639
    Type: Grant
    Filed: January 9, 2013
    Date of Patent: October 15, 2013
    Assignee: Koshin Ltd.
    Inventor: Kunihiro Hirai