Title:
MANUFACTURING OF BRIDGED ARTIFICIAL NUCLEOSIDE
Document Type and Number:
WIPO Patent Application WO/2020/204022
Kind Code:
A1
Abstract:
Provided is a method for manufacturing a compound represented by formula (III) by using, as a material, a compound represented by formula (I).
Inventors:
BABA TAKESHI (JP)
OKAMOTO HIROSHI (JP)
NOMURA YUMI (JP)
OBIKA SATOSHI (JP)
YAMAGUCHI TAKAO (JP)
OKAMOTO HIROSHI (JP)
NOMURA YUMI (JP)
OBIKA SATOSHI (JP)
YAMAGUCHI TAKAO (JP)
Application Number:
PCT/JP2020/014764
Publication Date:
October 08, 2020
Filing Date:
March 31, 2020
Export Citation:
Assignee:
NIPPON CATALYTIC CHEM IND (JP)
UNIV OSAKA (JP)
UNIV OSAKA (JP)
International Classes:
C07H1/00; C07H19/06; C07H19/16
Domestic Patent References:
| WO2009006478A2 | 2009-01-08 | |||
| WO2014126229A1 | 2014-08-21 | |||
| WO2018227168A1 | 2018-12-13 | |||
| WO2019133712A1 | 2019-07-04 | |||
| WO2015125783A1 | 2015-08-27 |
Foreign References:
| JP2001335592A | 2001-12-04 | |||
| JP2001335593A | 2001-12-04 | |||
| JP2004536817A | 2004-12-09 | |||
| JP2009504704A | 2009-02-05 | |||
| JP2016538829A | 2016-12-15 | |||
| JP2016530313A | 2016-09-29 | |||
| JP2017519784A | 2017-07-20 | |||
| JP2015151346A | 2015-08-24 | |||
| CN109893536A | 2019-06-18 |
Other References:
MITSUOKA YASUNORI, YAMAMOTO TSUYOSHI, KUGIMIYA AKIRA, WAKI REIKO, WADA FUMITO, TAHARA SAORI, SAWAMURA MOTOKI, NODA MIO, FUJIMURA Y: "Triazole- and Tetrazole-Bridged Nucleic Acids: Synthesis, Duplex Stability, Nuclease Resistance, and in Vitro and in Vivo Antisense Potency", JOURNAL OF ORGANIC CHEMISTRY, vol. 82, no. 1, 6 January 2017 (2017-01-06), pages 12 - 24, XP055746327
E. I. KODAMA, S. KOHGO, K. KITANO, H. MACHIDA, H. GATANAGA, S. SHIGETA, M. MATSUOKA, H. OHRUI, H. MITSUYA: "4'-ETHYNYL NUCLEOSIDE ANALOGS: POTENT INHIBITORS OF MULTIDRUG-RESISTANT HUMAN IMMUNODEFICIENCY VIRUS VARIANTS IN VITRO", ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, vol. 45, no. 5, 2001, pages 1539 - 1546, XP001127402
HIROSHI OHRUI, SATORU KOHGO, KENJI KITANO, SHINJI SAKATA, EIICHI KODAMA, KAZUHISA YOSHIMURA, MASAO MATSUOKA, SHIRO SHIGETA, AND HI: "Syntheses of 4‘-C-Ethynyl-β-d-arabino- and 4‘-C-Ethynyl-2‘-deoxy-β-d-ribo-pentofuranosylpyrimidines and -purines and Evaluation of Their Anti-HIV Activity", JOURNAL OF MEDICINAL CHEMISTRY, vol. 43, no. 23, 2000, pages 4516 - 4525, XP055058746
KOHGO S., KODAMA E., SHIGETA S., SANEYOSHI M., MACHIDA H., OHRUI H.: "Synthesis of 4'-substituted nucleosides and their biological evaluation", NUCLEIC ACIDS SYMPOSIUM SERIES, vol. 42, 1999, pages 127 - 128, XP055746343
KOHGO S; HORIE H; OHRUI H: "SYNTHESIS OF 4'-C-ETHYNYL-SS-D-ARABINO- AND 4'-C-ETHYNYL-2'-DEOXY-SS-D-RIBO-PENTOFURANOSYL PYRIMIDINES, AND THEIR BIOLOGICAL EVALUATION", BIOSCIENCE, BIOTECHNOLOGY, AND BIOCHEMISTRY, vol. 63, no. 6, 1999, pages 1146 - 1149, XP000915091
RITSUKO YAMAGUCHI,TATSUMA IMANISHI,SATORU KOHGO,HIROKO HORIE &HIROSHI OHRUIDEPARTMENT OF A: "SYNTHESIS OF 4'-C-ETHYNYL-SS-D-RIBO-PENTOFURANOSYL PYRIMIDINES", BIOSCIENCE, BIOTECHNOLOGY, AND BIOCHEMISTRY, vol. 63, no. 4, 1999, pages 736 - 742, XP000915092
FUKUYAMA KEI, OHRUI HIROSHI, KUWAHARA SHIGEFUMI: "Synthesis of EFdA via a Diastereoselective Aldol Reaction of a Protected 3‑Keto Furanose", ORGANIC LETTERS, vol. 17, no. 4, 2015, pages 828 - 831, XP055746348
HIROSHI OHRUI: "Chapter 16. 4′-C-Ethynyl-2′-Deoxynucleosides", TETRAHEDRON LETTERS, vol. 29, 2008, pages 425 - 431, XP055456328
SMITH DAVID B., MARTIN JOSEPH A., KLUMPP KLAUS, BAKER STEWART J., BLOMGREN PETER A., DEVOS RENE, GRANYCOME CAROLINE, HANG JULIE, H: "Design, synthesis, and antiviral properties of 4'-substituted ribonucleosides as inhibitors of hepatitis C virus replication: The discovery of R1479", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 17, no. 9, 2007, pages 2570 - 2576, XP022015347
NOMURA MAKOTO, SHUTO SATOSHI, TANAKA MOTOHIRO, SASAKI TAKUMA, MORI SHUICHI, SHIGETA SHIRO, MATSUDA AKIRA: "Nucleosides and Nucleotides. 185. Synthesis and Biological Activities of 4‘α- C -Branched-Chain Sugar Pyrimidine Nucleosides", JOURNAL OF MEDICINAL CHEMISTRY, vol. 42, no. 15, 1999, pages 2901 - 2908, XP000915083
WERTH JACOB, UYEDA CHRISTOPHER: "Regioselective Simmons–Smith-type cyclopropanations of polyalkenes enabled by transition metal catalysis", CHEM. SCI., vol. 9, no. 6, 2018, pages 1604 - 1609, XP055746383
CHEM. COMMUN., vol. 51, 2015, pages 9737 - 9740
J. ORG. CHEM., vol. 81, 2016, pages 11000 - 11008
E. I. KODAMA, S. KOHGO, K. KITANO, H. MACHIDA, H. GATANAGA, S. SHIGETA, M. MATSUOKA, H. OHRUI, H. MITSUYA: "4'-ETHYNYL NUCLEOSIDE ANALOGS: POTENT INHIBITORS OF MULTIDRUG-RESISTANT HUMAN IMMUNODEFICIENCY VIRUS VARIANTS IN VITRO", ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, vol. 45, no. 5, 2001, pages 1539 - 1546, XP001127402
HIROSHI OHRUI, SATORU KOHGO, KENJI KITANO, SHINJI SAKATA, EIICHI KODAMA, KAZUHISA YOSHIMURA, MASAO MATSUOKA, SHIRO SHIGETA, AND HI: "Syntheses of 4‘-C-Ethynyl-β-d-arabino- and 4‘-C-Ethynyl-2‘-deoxy-β-d-ribo-pentofuranosylpyrimidines and -purines and Evaluation of Their Anti-HIV Activity", JOURNAL OF MEDICINAL CHEMISTRY, vol. 43, no. 23, 2000, pages 4516 - 4525, XP055058746
KOHGO S., KODAMA E., SHIGETA S., SANEYOSHI M., MACHIDA H., OHRUI H.: "Synthesis of 4'-substituted nucleosides and their biological evaluation", NUCLEIC ACIDS SYMPOSIUM SERIES, vol. 42, 1999, pages 127 - 128, XP055746343
KOHGO S; HORIE H; OHRUI H: "SYNTHESIS OF 4'-C-ETHYNYL-SS-D-ARABINO- AND 4'-C-ETHYNYL-2'-DEOXY-SS-D-RIBO-PENTOFURANOSYL PYRIMIDINES, AND THEIR BIOLOGICAL EVALUATION", BIOSCIENCE, BIOTECHNOLOGY, AND BIOCHEMISTRY, vol. 63, no. 6, 1999, pages 1146 - 1149, XP000915091
RITSUKO YAMAGUCHI,TATSUMA IMANISHI,SATORU KOHGO,HIROKO HORIE &HIROSHI OHRUIDEPARTMENT OF A: "SYNTHESIS OF 4'-C-ETHYNYL-SS-D-RIBO-PENTOFURANOSYL PYRIMIDINES", BIOSCIENCE, BIOTECHNOLOGY, AND BIOCHEMISTRY, vol. 63, no. 4, 1999, pages 736 - 742, XP000915092
FUKUYAMA KEI, OHRUI HIROSHI, KUWAHARA SHIGEFUMI: "Synthesis of EFdA via a Diastereoselective Aldol Reaction of a Protected 3‑Keto Furanose", ORGANIC LETTERS, vol. 17, no. 4, 2015, pages 828 - 831, XP055746348
HIROSHI OHRUI: "Chapter 16. 4′-C-Ethynyl-2′-Deoxynucleosides", TETRAHEDRON LETTERS, vol. 29, 2008, pages 425 - 431, XP055456328
SMITH DAVID B., MARTIN JOSEPH A., KLUMPP KLAUS, BAKER STEWART J., BLOMGREN PETER A., DEVOS RENE, GRANYCOME CAROLINE, HANG JULIE, H: "Design, synthesis, and antiviral properties of 4'-substituted ribonucleosides as inhibitors of hepatitis C virus replication: The discovery of R1479", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 17, no. 9, 2007, pages 2570 - 2576, XP022015347
NOMURA MAKOTO, SHUTO SATOSHI, TANAKA MOTOHIRO, SASAKI TAKUMA, MORI SHUICHI, SHIGETA SHIRO, MATSUDA AKIRA: "Nucleosides and Nucleotides. 185. Synthesis and Biological Activities of 4‘α- C -Branched-Chain Sugar Pyrimidine Nucleosides", JOURNAL OF MEDICINAL CHEMISTRY, vol. 42, no. 15, 1999, pages 2901 - 2908, XP000915083
WERTH JACOB, UYEDA CHRISTOPHER: "Regioselective Simmons–Smith-type cyclopropanations of polyalkenes enabled by transition metal catalysis", CHEM. SCI., vol. 9, no. 6, 2018, pages 1604 - 1609, XP055746383
CHEM. COMMUN., vol. 51, 2015, pages 9737 - 9740
J. ORG. CHEM., vol. 81, 2016, pages 11000 - 11008
Attorney, Agent or Firm:
IWATANI, Ryo (JP)
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