Title:
BENZIMIDAZOLE COMPOUND HAVING ENDOTHELIAL LIPASE INHIBITION EFFECT, AND APPLICATION
Document Type and Number:
WIPO Patent Application WO/2022/057930
Kind Code:
A1
Abstract:
The present invention relates to the technical field of medicines. Disclosed are a benzimidazole compound having an endothelial lipase inhibition effect, and an application. The benzimidazole compound of the present invention has an excellent inhibition effect on endothelial lipase, can effectively treat atherosclerosis and sequelae thereof, such as coronary heart disease, and also promotes the treatment of metabolic syndrome and sequelae thereof, such as diabetes. The benzimidazole compound of the present invention has good solubility in an aqueous medium, good biological activity and good metabolic stability, and shows an advantage in respect of serum stability.
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| WO/2024/058617 | ANTIVIRAL USE OF HETEROARYL DERIVATIVE COMPOUND |
Inventors:
SUN YAQUAN (CN)
ZHANG LIJIE (CN)
CAO JINMING (CN)
YANG KANG (CN)
LI CHENYU (CN)
ZHANG LIJIE (CN)
CAO JINMING (CN)
YANG KANG (CN)
LI CHENYU (CN)
Application Number:
PCT/CN2021/119412
Publication Date:
March 24, 2022
Filing Date:
September 18, 2021
Export Citation:
Assignee:
YANCHENG NORMAL UNIV (CN)
International Classes:
C07D235/18; A61K31/4184; A61K31/443; A61K31/4436; A61K31/4439; A61P3/00; A61P3/04; A61P3/06; A61P3/10; A61P9/04; A61P11/06; A61P17/00; A61P19/06; A61P25/00; A61P35/00; C07D235/08; C07D401/04; C07D405/04; C07D409/04
Foreign References:
| CN111978301A | 2020-11-24 | |||
| CN102271511A | 2011-12-07 |
Other References:
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SADIG JESSIE E. R., FOSTER RADLEIGH, WAKENHUT FLORIAN, WILLIS MICHAEL C.: "Palladium-Catalyzed Synthesis of Benzimidazoles and Quinazolinones from Common Precursors", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 77, no. 21, 2 November 2012 (2012-11-02), pages 9473 - 9486, XP055912512, ISSN: 0022-3263, DOI: 10.1021/jo301805d
GOKANAPALLI ANUSHA, VENKATA KRISHNA REDDY MOTAKATLA, VASU GOVARDHANA REDDY PEDDIAHGARI: "Benzimidazole Bearing Pd–PEPPSI Complexes Catalyzed Direct C2-arylation/heteroarylation of N-substituted Benzimidazoles", APPLIED ORGANOMETALLIC CHEMISTRY, vol. 34, no. 10, 26 January 2020 (2020-01-26), XP055912516, DOI: 10.1002/aoc.5869
XIE CAIXIA, HAN XUSHUANG, GONG JIAN, LI DANYANG, MA CHEN: "One-pot strategy of copper-catalyzed synthesis of 1,2-disubstituted benzimidazoles", ORGANIC & BIOMOLECULAR CHEMISTRY, ROYAL SOCIETY OF CHEMISTRY, vol. 15, no. 27, 1 January 2017 (2017-01-01), pages 5811 - 5819, XP055912520, ISSN: 1477-0520, DOI: 10.1039/C7OB00945C
ZHOULONG FAN, JIABIN NI, AO ZHANG: "Meta-Selective C Ar –H Nitration of Arenes through a Ru 3 (CO) 12 -Catalyzed Ortho-Metalation Strategy", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 138, no. 27, 13 July 2016 (2016-07-13), pages 8470 - 8475, XP055471742, ISSN: 0002-7863, DOI: 10.1021/jacs.6b03402
LIN JIAN-PING, ZHANG FENG-HUA, LONG YA-QIU: "Solvent/Oxidant-Switchable Synthesis of Multisubstituted Quinazolines and Benzimidazoles via Metal-Free Selective Oxidative Annulation of Arylamidines", ORGANIC LETTERS, AMERICAN CHEMICAL SOCIETY, US, vol. 16, no. 11, 6 June 2014 (2014-06-06), US , pages 2822 - 2825, XP055912523, ISSN: 1523-7060, DOI: 10.1021/ol500864r
XIN PENGYANG, GUO HAI-MING, XIN PENG-YANG, NIU HONG-YING, QU GUI-RONG, DING RUI-FANG: "ChemInform Abstract: Nickel Catalyzed Alkylation of N-Aromatic Heterocycles with Grignard Reagents Through Direct C-H Bond Functionalization. Nickel catalyzed alkylation of N-aromatic heterocycles with Grignard reagents through direct C–H bond functionalizationw", CHEM. COMMUN. CHEM. COMMUN, vol. 48, no. 53, 9 May 2012 (2012-05-09), pages 6717 - 6719, XP055912526, DOI: 10.1039/c2cc32396f·Source:
KOMMI DAMODARA N., KUMAR DINESH, BANSAL ROHIT, CHEBOLU RAJESH, CHAKRABORTI ASIT K.: "“All-water” chemistry of tandem N-alkylation–reduction–condensation for synthesis of N-arylmethyl-2-substituted benzimidazoles", GREEN CHEMISTRY, ROYAL SOCIETY OF CHEMISTRY, GB, vol. 14, no. 12, 1 January 2012 (2012-01-01), GB , pages 3329, XP055912527, ISSN: 1463-9262, DOI: 10.1039/c2gc36377a
DATABASE REGISTRY 10 April 2006 (2006-04-10), ANONYMOUS : "1H-Benzimidazole, 2-(2-methylphenyl)-1-(phenylmethyl)- (CA INDEX NAME)", XP055912597, retrieved from STN Database accession no. 879918-94-2
DATABASE REGISTRY 16 January 2004 (2004-01-16), ANONYMOUS : "1H-Benzimidazole, 2-(3-methylphenyl)-1-(phenylmethyl)- (CA INDEX NAME)", XP055912601, retrieved from STN Database accession no. 638141-26-1
DATABASE REGISTRY 26 June 2007 (2007-06-26), ANONYMOUS : "1H-Benzimidazole, 1-(2-phenylethyl)-2-(2-pyridinyl)- (CA INDEX NAME) ", XP055912604, retrieved from STN Database accession no. 939242-15-6
SADIG JESSIE E. R., FOSTER RADLEIGH, WAKENHUT FLORIAN, WILLIS MICHAEL C.: "Palladium-Catalyzed Synthesis of Benzimidazoles and Quinazolinones from Common Precursors", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 77, no. 21, 2 November 2012 (2012-11-02), pages 9473 - 9486, XP055912512, ISSN: 0022-3263, DOI: 10.1021/jo301805d
GOKANAPALLI ANUSHA, VENKATA KRISHNA REDDY MOTAKATLA, VASU GOVARDHANA REDDY PEDDIAHGARI: "Benzimidazole Bearing Pd–PEPPSI Complexes Catalyzed Direct C2-arylation/heteroarylation of N-substituted Benzimidazoles", APPLIED ORGANOMETALLIC CHEMISTRY, vol. 34, no. 10, 26 January 2020 (2020-01-26), XP055912516, DOI: 10.1002/aoc.5869
XIE CAIXIA, HAN XUSHUANG, GONG JIAN, LI DANYANG, MA CHEN: "One-pot strategy of copper-catalyzed synthesis of 1,2-disubstituted benzimidazoles", ORGANIC & BIOMOLECULAR CHEMISTRY, ROYAL SOCIETY OF CHEMISTRY, vol. 15, no. 27, 1 January 2017 (2017-01-01), pages 5811 - 5819, XP055912520, ISSN: 1477-0520, DOI: 10.1039/C7OB00945C
ZHOULONG FAN, JIABIN NI, AO ZHANG: "Meta-Selective C Ar –H Nitration of Arenes through a Ru 3 (CO) 12 -Catalyzed Ortho-Metalation Strategy", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 138, no. 27, 13 July 2016 (2016-07-13), pages 8470 - 8475, XP055471742, ISSN: 0002-7863, DOI: 10.1021/jacs.6b03402
LIN JIAN-PING, ZHANG FENG-HUA, LONG YA-QIU: "Solvent/Oxidant-Switchable Synthesis of Multisubstituted Quinazolines and Benzimidazoles via Metal-Free Selective Oxidative Annulation of Arylamidines", ORGANIC LETTERS, AMERICAN CHEMICAL SOCIETY, US, vol. 16, no. 11, 6 June 2014 (2014-06-06), US , pages 2822 - 2825, XP055912523, ISSN: 1523-7060, DOI: 10.1021/ol500864r
XIN PENGYANG, GUO HAI-MING, XIN PENG-YANG, NIU HONG-YING, QU GUI-RONG, DING RUI-FANG: "ChemInform Abstract: Nickel Catalyzed Alkylation of N-Aromatic Heterocycles with Grignard Reagents Through Direct C-H Bond Functionalization. Nickel catalyzed alkylation of N-aromatic heterocycles with Grignard reagents through direct C–H bond functionalizationw", CHEM. COMMUN. CHEM. COMMUN, vol. 48, no. 53, 9 May 2012 (2012-05-09), pages 6717 - 6719, XP055912526, DOI: 10.1039/c2cc32396f·Source:
KOMMI DAMODARA N., KUMAR DINESH, BANSAL ROHIT, CHEBOLU RAJESH, CHAKRABORTI ASIT K.: "“All-water” chemistry of tandem N-alkylation–reduction–condensation for synthesis of N-arylmethyl-2-substituted benzimidazoles", GREEN CHEMISTRY, ROYAL SOCIETY OF CHEMISTRY, GB, vol. 14, no. 12, 1 January 2012 (2012-01-01), GB , pages 3329, XP055912527, ISSN: 1463-9262, DOI: 10.1039/c2gc36377a
DATABASE REGISTRY 10 April 2006 (2006-04-10), ANONYMOUS : "1H-Benzimidazole, 2-(2-methylphenyl)-1-(phenylmethyl)- (CA INDEX NAME)", XP055912597, retrieved from STN Database accession no. 879918-94-2
DATABASE REGISTRY 16 January 2004 (2004-01-16), ANONYMOUS : "1H-Benzimidazole, 2-(3-methylphenyl)-1-(phenylmethyl)- (CA INDEX NAME)", XP055912601, retrieved from STN Database accession no. 638141-26-1
DATABASE REGISTRY 26 June 2007 (2007-06-26), ANONYMOUS : "1H-Benzimidazole, 1-(2-phenylethyl)-2-(2-pyridinyl)- (CA INDEX NAME) ", XP055912604, retrieved from STN Database accession no. 939242-15-6
Attorney, Agent or Firm:
BEIJING ZHUOSHENG BAIDA IP AGENT LTD. (CN)
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