Title:
NOVEL BENZIMIDAZOLE DERIVATIVE, PREPARATION METHOD THEREFOR, AND USE THEREOF AS ANTICANCER OR ANTIVIRAL AGENT
Document Type and Number:
WIPO Patent Application WO/2021/261663
Kind Code:
A1
Abstract:
According to the present invention, provided are a benzimidazole-carbohydrate conjugate compound represented by chemical formula 1, a preparation method therefor, and a use thereof as an anticancer or antiviral agent. [Chemical formula 1] (In chemical formula 1, R 1, R 2, R 3 and X are as defined in the specification and claims.)
Inventors:
KIM JUNGHUN (KR)
SONG KEUMSOO (KR)
KIM TAISUN (KR)
SONG KEUMSOO (KR)
KIM TAISUN (KR)
Application Number:
PCT/KR2020/013371
Publication Date:
December 30, 2021
Filing Date:
September 29, 2020
Export Citation:
Assignee:
BIOMETRIX TECH INC (KR)
International Classes:
C07H17/02; A61K31/7052; A61P31/12; A61P35/00; C07H1/00
Domestic Patent References:
| WO2016109880A1 | 2016-07-14 | |||
| WO1998056761A2 | 1998-12-17 | |||
| WO1998051304A1 | 1998-11-19 | |||
| WO2005058870A1 | 2005-06-30 | |||
| WO1998056761A2 | 1998-12-17 |
Other References:
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SMELLIE, I.A.S. ; FROMM, A. ; FABBIANI, F. ; OSWALD, I.D.H. ; WHITE, F.J. ; PATON, R.M.: "Synthesis of 2-pyranosyl benzothiazoles, benzimidazoles and benzoxazoles via nucleophilic addition reactions of pyranosyl nitrile oxides", TETRAHEDRON, ELSEVIER SIENCE PUBLISHERS, AMSTERDAM, NL, vol. 66, no. 35, 28 August 2010 (2010-08-28), AMSTERDAM, NL , pages 7155 - 7160, XP027184973, ISSN: 0040-4020, DOI: 10.1016/j.tet.2010.06.076
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EL-NEZHAWY AHMED, GABALLAH SAMIR, RADWAN MOHAMED, BAIUOMY AYMAN, ABDEL-SALAM OMAR: "Structure-Based Design of Benzimidazole Sugar Conjugates: Synthesis, SAR and In Vivo Anti-inflammatory and Analgesic Activities", MEDICINAL CHEMISTRY, BENTHAM SCIENCE PUBLISHERS LTD., NL, vol. 5, no. 6, 1 November 2009 (2009-11-01), NL , pages 558 - 569, XP055884370, ISSN: 1573-4064, DOI: 10.2174/157340609790170461
CHEM BIOL DRUG DES., vol. 90, no. 1, July 2017 (2017-07-01), pages 40 - 51
SCIENTIFIC REPORTS, vol. 8, 2018, pages 11926
ANTICANCER RESEARCH, vol. 29, 2009, pages 3791 - 3796
L. QUAN ET AL., JOURNAL OF MOLECULAR STRUCTURE, vol. 1203, 2020, pages 127361
EXPERIMENTAL AND THERAPEUTIC MEDICINE, vol. 13, 2017, pages 595 - 603
VOJNOSANIT PREGL., vol. 65, no. 7, July 2008 (2008-07-01), pages 539 - 44
INFECT CHEMOTHER, vol. 50, no. 1, 2018, pages 1 - 10
BMC BIOLOGY, vol. 17, 2019, pages 59
J VIROL, vol. 89, pages 2358 - 2366
VIROLOGY, vol. 444, no. 1-2, 2013, pages 301 - 9
MOL CANCER THER, vol. 11, no. 1, January 2012 (2012-01-01), pages 14 - 23
L. QUAN ET AL., JOURNAL OF MOLECULAR STRUCTURE, vol. 1203, no. 2020, pages 127361
GOKHALEKEARNEYKIRSCH, AAPS PHARMSCITECH, vol. 10, no. 2, June 2009 (2009-06-01)
CAS , no. 80983-36-4
SLATER, T. ET AL., BIOCHEM. BIOPHYS. ACTA, vol. 77, 1963, pages 383
VAN DE LOOSDRECHT, AA ET AL., J. IMMUNOL. METHODS, vol. 174, 1994, pages 311 - 320
ALLEY, MC ET AL., CANCER RES., vol. 48, 1988, pages 589 - 601
SMELLIE, I.A.S. ; FROMM, A. ; FABBIANI, F. ; OSWALD, I.D.H. ; WHITE, F.J. ; PATON, R.M.: "Synthesis of 2-pyranosyl benzothiazoles, benzimidazoles and benzoxazoles via nucleophilic addition reactions of pyranosyl nitrile oxides", TETRAHEDRON, ELSEVIER SIENCE PUBLISHERS, AMSTERDAM, NL, vol. 66, no. 35, 28 August 2010 (2010-08-28), AMSTERDAM, NL , pages 7155 - 7160, XP027184973, ISSN: 0040-4020, DOI: 10.1016/j.tet.2010.06.076
KHARITONOVA M I, KONSTANTINOVA I D, MIROSHNIKOV A I: "Benzimidazole nucleosides: antiviral and antitumour activities and methods of synthesis", RUSSIAN CHEMICAL REVIEWS (TRANSLATED FROM USPEKHI KHIMII), vol. 87, no. 11, 30 November 2018 (2018-11-30), pages 1111 - 1138, XP055884364, ISSN: 0036-021X, DOI: 10.1070/RCR4832
EL-NEZHAWY AHMED, GABALLAH SAMIR, RADWAN MOHAMED, BAIUOMY AYMAN, ABDEL-SALAM OMAR: "Structure-Based Design of Benzimidazole Sugar Conjugates: Synthesis, SAR and In Vivo Anti-inflammatory and Analgesic Activities", MEDICINAL CHEMISTRY, BENTHAM SCIENCE PUBLISHERS LTD., NL, vol. 5, no. 6, 1 November 2009 (2009-11-01), NL , pages 558 - 569, XP055884370, ISSN: 1573-4064, DOI: 10.2174/157340609790170461
CHEM BIOL DRUG DES., vol. 90, no. 1, July 2017 (2017-07-01), pages 40 - 51
SCIENTIFIC REPORTS, vol. 8, 2018, pages 11926
ANTICANCER RESEARCH, vol. 29, 2009, pages 3791 - 3796
L. QUAN ET AL., JOURNAL OF MOLECULAR STRUCTURE, vol. 1203, 2020, pages 127361
EXPERIMENTAL AND THERAPEUTIC MEDICINE, vol. 13, 2017, pages 595 - 603
VOJNOSANIT PREGL., vol. 65, no. 7, July 2008 (2008-07-01), pages 539 - 44
INFECT CHEMOTHER, vol. 50, no. 1, 2018, pages 1 - 10
BMC BIOLOGY, vol. 17, 2019, pages 59
J VIROL, vol. 89, pages 2358 - 2366
VIROLOGY, vol. 444, no. 1-2, 2013, pages 301 - 9
MOL CANCER THER, vol. 11, no. 1, January 2012 (2012-01-01), pages 14 - 23
L. QUAN ET AL., JOURNAL OF MOLECULAR STRUCTURE, vol. 1203, no. 2020, pages 127361
GOKHALEKEARNEYKIRSCH, AAPS PHARMSCITECH, vol. 10, no. 2, June 2009 (2009-06-01)
CAS , no. 80983-36-4
SLATER, T. ET AL., BIOCHEM. BIOPHYS. ACTA, vol. 77, 1963, pages 383
VAN DE LOOSDRECHT, AA ET AL., J. IMMUNOL. METHODS, vol. 174, 1994, pages 311 - 320
ALLEY, MC ET AL., CANCER RES., vol. 48, 1988, pages 589 - 601
Attorney, Agent or Firm:
DAE-A INTELLECTUAL PROPERTY CONSULTING (KR)
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