Title:
ANTIPLATELET DRUGS AND USES THEREOF
Document Type and Number:
WIPO Patent Application WO/2022/022559
Kind Code:
A1
Abstract:
The present disclosure relates to compounds which exhibit activity in the inhibition of platelet aggregation as well as pharmaceutical compositions comprising these compounds and methods of treatment of vascular diseases by administration of these compounds or the pharmaceutical compositions.
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Inventors:
GU ZI-QIANG (US)
ZHANG YUANCHAO (US)
HE GONGXIN (CN)
HOU KAI (CN)
WU HAO (CN)
ZHANG YUANCHAO (US)
HE GONGXIN (CN)
HOU KAI (CN)
WU HAO (CN)
Application Number:
PCT/CN2021/108875
Publication Date:
February 03, 2022
Filing Date:
July 28, 2021
Export Citation:
Assignee:
SHANGHAI CUREGENE PHARMACEUTICAL CO LTD (CN)
International Classes:
C07F9/59; A61K31/675; A61P9/10; C07D211/72; C07J43/00
Foreign References:
| CN106554368A | 2017-04-05 | |||
| CN106554303A | 2017-04-05 |
Other References:
BLUET GUILLAUME; BLANKENSTEIN JORG; BROHAN ERIC; PRÉVOST CÉLINE; CHEVÉ MICHEL; SCHOFIELD JOSEPH; ROY SÉBASTIEN : "Synthesis of the stabilized active metabolite of clopidogrel", TETRAHEDRON, vol. 70, no. 25, 1 January 1900 (1900-01-01), AMSTERDAM, NL , pages 3893 - 3900, XP028664939, ISSN: 0040-4020, DOI: 10.1016/j.tet.2014.04.037
TAKAHASHI, M. ; PANG, H. ; KAWABATA, K. ; FARID, N.A. ; KURIHARA, A.: "Quantitative determination of clopidogrel active metabolite in human plasma by LC-MS/MS", JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, vol. 48, no. 4, 1 December 2008 (2008-12-01), AMSTERDAM, NL , pages 1219 - 1224, XP025839883, ISSN: 0731-7085, DOI: 10.1016/j.jpba.2008.08.020
LIU CAI, LU YOUMING, SUN HONGBIN, YANG JIN, LIU YONGQIANG, LAI XIAOJUAN, GONG YANCHUN, LIU XUEFANG, LI YONGGUO, ZHANG YIFAN, CHEN : "Development and validation of a sensitive and rapid UHPLC–MS/MS method for the simultaneous quantification of the common active and inactive metabolites of vicagrel and clopidogrel in human plasma", JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, vol. 149, 1 February 2018 (2018-02-01), AMSTERDAM, NL , pages 394 - 402, XP055892338, ISSN: 0731-7085, DOI: 10.1016/j.jpba.2017.11.019
FURLONG MICHAEL T.; SAVANT ISHANI; YUAN MOUCUN; SCOTT LAURA; MYLOTT WILLIAM; MARIANNINO THOMAS; KADIYALA PATHANJALI; ROONGTA VIKRA: "A validated HPLC–MS/MS assay for quantifying unstable pharmacologically active metabolites of clopidogrel in human plasma: Application to a clinical pharmacokinetic study", JOURNAL OF CHROMATOGRAPHY B, vol. 926, 1 March 2013 (2013-03-01), NL , pages 36 - 41, XP028545018, ISSN: 1570-0232, DOI: 10.1016/j.jchromb.2013.02.031
SCOTT A. SHAW, BALU BALASUBRAMANIAN, SAMUEL BONACORSI, JANET CACERES CORTES, KEVIN CAO, BANG-CHI CHEN, JUN DAI, CARL DECICCO, ANIM: "Synthesis of Biologically Active Piperidine Metabolites of Clopidogrel: Determination of Structure and Analyte Development", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 80, no. 14, 17 July 2015 (2015-07-17), pages 7019 - 7032, XP055398316, ISSN: 0022-3263, DOI: 10.1021/acs.joc.5b00632
NAGY A. FARID, MARY MCINTOSH, FABIO GAROFOLO, ERNEST WONG, AMANDA SHWAJCH, MONIKA KENNEDY, MICHELLE YOUNG, PRATIBHA SARKAR, KIYOSH: "Determination of the active and inactive metabolites of prasugrel in human plasma by liquid chromatography/tandem mass spectrometry", RAPID COMMUNICATIONS IN MASS SPECTROMETRY, vol. 21, no. 2, 30 January 2007 (2007-01-30), GB , pages 169 - 179, XP055273031, ISSN: 0951-4198, DOI: 10.1002/rcm.2813
HAGIHARA KATSUNOBU, KAZUI MIHO, KURIHARA ATSUSHI, IKEDA TOSHIHIKO, IZUMI TAKASHI: "Glutaredoxin Is Involved in the Formation of the Pharmacologically Active Metabolite of Clopidogrel from Its GSH Conjugate", DRUG METABOLISM AND DISPOSITION, vol. 40, no. 9, 31 December 2012 (2012-12-31), US , pages 1854 - 1859, XP009533675, ISSN: 0090-9556, DOI: 10.1124/dmd.112.045914
DELAVENNE XAVIER, BASSET THIERRY, ZUFFEREY PAUL, MALOUK NORA, LAPORTE SILVY, MISMETTI PATRICK: "Ultra-performance LC MS/MS method for quantification of clopidogrel active metabolite", JOURNAL OF SEPARATION SCIENCE, vol. 33, no. 13, 1 July 2010 (2010-07-01), DE , pages 1968 - 1972, XP055892342, ISSN: 1615-9306, DOI: 10.1002/jssc.201000115
DANSETTE PATRICK M., ROSI JULIEN, DEBERNARDI JUSTINE, BERTHO GILDAS, MANSUY DANIEL: "Metabolic Activation of Prasugrel: Nature of the Two Competitive Pathways Resulting in the Opening of Its Thiophene Ring", CHEMICAL RESEARCH IN TOXICOLOGY, vol. 25, no. 5, 21 May 2012 (2012-05-21), US , pages 1058 - 1065, XP055892348, ISSN: 0893-228X, DOI: 10.1021/tx3000279
TIAN XI; YANG XIULING; ZHANG ZHIQING; WANG SHUMEI; DONG WEICHONG: "Determination of Clopidogrel and Its Active Metabolite in Human Plasma by LC-MS/MS，", CHINESE JOURNAL OF PHARMACEUTICALS, vol. 47, no. 2, 31 December 2016 (2016-12-31), CN , pages 202 - 206, XP009533673, ISSN: 1001-8255, DOI: 10.16522/j.cnki.cjph.2016.02.016
LIU, SHUAI-BING; WANG, ZI-TENG; DING, XIAO-LIANG; XU, QING-QING; GUO, ZHE-NING; MIAO, LI-YAN: "Determination of clopidogrel and its metabolites in plasma by UPLC-MS/MS and the application in pharmacokinetic study，", CHINESE JOURNAL OF PHARMACEUTICAL ANALYSIS, vol. 35, no. 1, 31 December 2015 (2015-12-31), pages 56 - 63, XP009533642, ISSN: 0254-1793
TAKAHASHI, M. ; PANG, H. ; KAWABATA, K. ; FARID, N.A. ; KURIHARA, A.: "Quantitative determination of clopidogrel active metabolite in human plasma by LC-MS/MS", JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, vol. 48, no. 4, 1 December 2008 (2008-12-01), AMSTERDAM, NL , pages 1219 - 1224, XP025839883, ISSN: 0731-7085, DOI: 10.1016/j.jpba.2008.08.020
LIU CAI, LU YOUMING, SUN HONGBIN, YANG JIN, LIU YONGQIANG, LAI XIAOJUAN, GONG YANCHUN, LIU XUEFANG, LI YONGGUO, ZHANG YIFAN, CHEN : "Development and validation of a sensitive and rapid UHPLC–MS/MS method for the simultaneous quantification of the common active and inactive metabolites of vicagrel and clopidogrel in human plasma", JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, vol. 149, 1 February 2018 (2018-02-01), AMSTERDAM, NL , pages 394 - 402, XP055892338, ISSN: 0731-7085, DOI: 10.1016/j.jpba.2017.11.019
FURLONG MICHAEL T.; SAVANT ISHANI; YUAN MOUCUN; SCOTT LAURA; MYLOTT WILLIAM; MARIANNINO THOMAS; KADIYALA PATHANJALI; ROONGTA VIKRA: "A validated HPLC–MS/MS assay for quantifying unstable pharmacologically active metabolites of clopidogrel in human plasma: Application to a clinical pharmacokinetic study", JOURNAL OF CHROMATOGRAPHY B, vol. 926, 1 March 2013 (2013-03-01), NL , pages 36 - 41, XP028545018, ISSN: 1570-0232, DOI: 10.1016/j.jchromb.2013.02.031
SCOTT A. SHAW, BALU BALASUBRAMANIAN, SAMUEL BONACORSI, JANET CACERES CORTES, KEVIN CAO, BANG-CHI CHEN, JUN DAI, CARL DECICCO, ANIM: "Synthesis of Biologically Active Piperidine Metabolites of Clopidogrel: Determination of Structure and Analyte Development", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 80, no. 14, 17 July 2015 (2015-07-17), pages 7019 - 7032, XP055398316, ISSN: 0022-3263, DOI: 10.1021/acs.joc.5b00632
NAGY A. FARID, MARY MCINTOSH, FABIO GAROFOLO, ERNEST WONG, AMANDA SHWAJCH, MONIKA KENNEDY, MICHELLE YOUNG, PRATIBHA SARKAR, KIYOSH: "Determination of the active and inactive metabolites of prasugrel in human plasma by liquid chromatography/tandem mass spectrometry", RAPID COMMUNICATIONS IN MASS SPECTROMETRY, vol. 21, no. 2, 30 January 2007 (2007-01-30), GB , pages 169 - 179, XP055273031, ISSN: 0951-4198, DOI: 10.1002/rcm.2813
HAGIHARA KATSUNOBU, KAZUI MIHO, KURIHARA ATSUSHI, IKEDA TOSHIHIKO, IZUMI TAKASHI: "Glutaredoxin Is Involved in the Formation of the Pharmacologically Active Metabolite of Clopidogrel from Its GSH Conjugate", DRUG METABOLISM AND DISPOSITION, vol. 40, no. 9, 31 December 2012 (2012-12-31), US , pages 1854 - 1859, XP009533675, ISSN: 0090-9556, DOI: 10.1124/dmd.112.045914
DELAVENNE XAVIER, BASSET THIERRY, ZUFFEREY PAUL, MALOUK NORA, LAPORTE SILVY, MISMETTI PATRICK: "Ultra-performance LC MS/MS method for quantification of clopidogrel active metabolite", JOURNAL OF SEPARATION SCIENCE, vol. 33, no. 13, 1 July 2010 (2010-07-01), DE , pages 1968 - 1972, XP055892342, ISSN: 1615-9306, DOI: 10.1002/jssc.201000115
DANSETTE PATRICK M., ROSI JULIEN, DEBERNARDI JUSTINE, BERTHO GILDAS, MANSUY DANIEL: "Metabolic Activation of Prasugrel: Nature of the Two Competitive Pathways Resulting in the Opening of Its Thiophene Ring", CHEMICAL RESEARCH IN TOXICOLOGY, vol. 25, no. 5, 21 May 2012 (2012-05-21), US , pages 1058 - 1065, XP055892348, ISSN: 0893-228X, DOI: 10.1021/tx3000279
TIAN XI; YANG XIULING; ZHANG ZHIQING; WANG SHUMEI; DONG WEICHONG: "Determination of Clopidogrel and Its Active Metabolite in Human Plasma by LC-MS/MS，", CHINESE JOURNAL OF PHARMACEUTICALS, vol. 47, no. 2, 31 December 2016 (2016-12-31), CN , pages 202 - 206, XP009533673, ISSN: 1001-8255, DOI: 10.16522/j.cnki.cjph.2016.02.016
LIU, SHUAI-BING; WANG, ZI-TENG; DING, XIAO-LIANG; XU, QING-QING; GUO, ZHE-NING; MIAO, LI-YAN: "Determination of clopidogrel and its metabolites in plasma by UPLC-MS/MS and the application in pharmacokinetic study，", CHINESE JOURNAL OF PHARMACEUTICAL ANALYSIS, vol. 35, no. 1, 31 December 2015 (2015-12-31), pages 56 - 63, XP009533642, ISSN: 0254-1793
Attorney, Agent or Firm:
JUN HE LAW OFFICES (CN)
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