KR101556808B1 - 비씨클로-치환된 피라졸론 아조 유도체, 그 제조 방법 및 약학적 용도 - Google Patents

비씨클로-치환된 피라졸론 아조 유도체, 그 제조 방법 및 약학적 용도 Download PDF

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KR101556808B1
KR101556808B1 KR1020107017630A KR20107017630A KR101556808B1 KR 101556808 B1 KR101556808 B1 KR 101556808B1 KR 1020107017630 A KR1020107017630 A KR 1020107017630A KR 20107017630 A KR20107017630 A KR 20107017630A KR 101556808 B1 KR101556808 B1 KR 101556808B1
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mixture
mmol
carboxylic acid
methyl
reaction
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KR20100120141A (ko
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펭 초 탕
헤준 류
하오 젱
이이퀴안 첸
홍보 페이
셴그란 왕
리 왕
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지앙수 헨그루이 메디슨 컴퍼니 리미티드
샹하이 헨그루이 파마수티컬 컴퍼니 리미티드
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    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D417/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61P7/04Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
    • AHUMAN NECESSITIES
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    • C07D231/00Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/06Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D231/08Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with oxygen or sulfur atoms directly attached to ring carbon atoms
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    • C07D231/10Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/18One oxygen or sulfur atom
    • C07D231/20One oxygen atom attached in position 3 or 5
    • C07D231/22One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
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    • C07D231/02Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/38Nitrogen atoms
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    • C07D405/00Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
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    • C07D405/04Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07D405/10Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
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    • C07D405/12Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07D409/00Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
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  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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  • Bioinformatics & Cheminformatics (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Hematology (AREA)
  • Diabetes (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
KR1020107017630A 2008-01-10 2009-01-04 비씨클로-치환된 피라졸론 아조 유도체, 그 제조 방법 및 약학적 용도 Active KR101556808B1 (ko)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN200810000346.6 2008-01-10
CNA2008100003466A CN101481352A (zh) 2008-01-10 2008-01-10 双环取代吡唑酮偶氮类衍生物、其制备方法及其在医药上的应用

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KR20100120141A KR20100120141A (ko) 2010-11-12
KR101556808B1 true KR101556808B1 (ko) 2015-10-01

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US (2) US8367710B2 (https=)
EP (1) EP2236500B1 (https=)
JP (1) JP5441269B2 (https=)
KR (1) KR101556808B1 (https=)
CN (2) CN101481352A (https=)
AU (1) AU2009207966B2 (https=)
BR (1) BRPI0907234B1 (https=)
CA (1) CA2711535C (https=)
ES (1) ES2533366T3 (https=)
MX (1) MX2010007553A (https=)
PT (1) PT2236500E (https=)
RU (1) RU2488582C2 (https=)
UA (1) UA101172C2 (https=)
WO (1) WO2009092276A1 (https=)
ZA (1) ZA201004794B (https=)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE0302486D0 (sv) * 2003-09-18 2003-09-18 Astrazeneca Ab Novel compounds
CN101921232A (zh) * 2009-06-11 2010-12-22 上海恒瑞医药有限公司 双环取代吡唑酮偶氮类衍生物的盐,其制备方法及其在医药上的应用
JP5704073B2 (ja) * 2009-10-23 2015-04-22 日産化学工業株式会社 縮環へテロ環化合物及びトロンボポエチンレセプター活性化剤
CN103360317B (zh) * 2012-04-11 2016-12-14 齐鲁制药有限公司 双环取代吡唑酮偶氮类衍生物、其制备方法及用途
CN103724206A (zh) * 2014-01-17 2014-04-16 青岛农业大学 化合物2-溴-4-氟-6-硝基苯酚的制备方法和农用生物活性
WO2015111085A2 (en) * 2014-01-27 2015-07-30 Cadila Healthcare Limited Processes for the preparation of eltrombopag and pharmaceutically acceptable salts, solvates and intermediates thereof
US9849077B2 (en) 2014-03-10 2017-12-26 Mary Kay Inc. Skin lightening compositions
CN104592033A (zh) * 2014-12-30 2015-05-06 杭州和泽医药科技有限公司 一种艾曲波帕关键中间体的合成方法
CN106994120B (zh) * 2016-01-22 2021-05-14 江苏恒瑞医药股份有限公司 一种含有双环取代吡唑酮偶氮类衍生物或其盐的药物组合物及其制备方法
TW201726129A (zh) * 2016-01-22 2017-08-01 江蘇恆瑞醫藥股份有限公司 一種含有雙環取代吡唑酮偶氮類衍生物或其鹽的藥物組成物及其製備方法
TWI762556B (zh) * 2017-01-19 2022-05-01 大陸商江蘇恆瑞醫藥股份有限公司 一種雙環取代吡唑酮偶氮類衍生物的製備方法及其中間體
CN110028497B (zh) * 2018-01-11 2020-11-17 江苏恒瑞医药股份有限公司 一种血小板生成素模拟物的乙醇胺盐的结晶形式及制备方法
CN113226463A (zh) * 2019-01-08 2021-08-06 江苏恒瑞医药股份有限公司 双环取代吡唑酮偶氮类衍生物的给药方案
CN112062699B (zh) * 2020-11-13 2021-02-26 苏州开元民生科技股份有限公司 一种邻氨基苯硫酚的制备方法
WO2022228551A1 (zh) * 2021-04-30 2022-11-03 江苏恒瑞医药股份有限公司 一种血小板生成素受体激动剂的给药方案
US20250144077A1 (en) * 2022-01-25 2025-05-08 Jiangsu Hengrui Pharmaceuticals Co., Ltd. Dosage regimen for thrombopoietin receptor agonist
WO2025140275A1 (zh) * 2023-12-25 2025-07-03 江苏恒瑞医药股份有限公司 取代吡唑啉偶氮衍生物的磷酸酯化合物或其可药用盐

Family Cites Families (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB775216A (en) * 1954-02-23 1957-05-22 Sandoz Ltd Improvements in or relating to monoazo dyestuffs of the benzene-azo-pyrazolone series and their chromium-complex compounds
GB806709A (en) * 1955-04-22 1958-12-31 Bayer Ag Monoazo dyestuffs of the benzene-azo-pyrazolone series and metal complexes thereof
TR199701526T1 (xx) 1995-06-07 1998-03-21 Glaxo Group Limited Bir trombopoietin resept�r�ne ba�lanan peptitler ve bile�ikler.
US5869451A (en) 1995-06-07 1999-02-09 Glaxo Group Limited Peptides and compounds that bind to a receptor
JPH111477A (ja) 1997-06-12 1999-01-06 Hokuriku Seiyaku Co Ltd 1,4−ベンゾジアゼピン誘導体及びその用途
AU9265698A (en) 1997-09-02 1999-03-22 Boehringer Mannheim Gmbh Mpl-receptor ligands, process for their preparation, medicaments containing themand their use for the treatment and prevention of thrombocytopaenia and anaemia
JP2002529502A (ja) 1998-11-17 2002-09-10 スミスクライン・ビーチャム・コーポレイション 血小板減少症の治療法
WO2000039773A1 (de) 1998-12-14 2000-07-06 Mannesmann Ag Verfahren zur übertragung von verkehrsinformationen
GC0000177A (en) 1998-12-17 2006-03-29 Smithkline Beecham Thrombopoietin mimetics
KR20020069183A (ko) 1999-07-26 2002-08-29 시오노기세이야쿠가부시키가이샤 트롬보포이에틴 작동성을 나타내는 의약 조성물
EP1213965B1 (en) 1999-09-10 2006-01-18 Smithkline Beecham Corporation Thrombopoietin mimetics
WO2001034585A1 (en) 1999-11-05 2001-05-17 Smithkline Beecham Corporation Semicarbazone derivatives and their use as thrombopoietin mimetics
AU2079901A (en) 1999-12-06 2001-06-12 Smithkline Beecham Corporation Thrombopoietin mimetics
TWI284639B (en) 2000-01-24 2007-08-01 Shionogi & Co A compound having thrombopoietin receptor agonistic effect
CY2010012I2 (el) * 2000-05-25 2020-05-29 Novartis Ag Μιμητικα θρομβοποιητινης
TWI280128B (en) * 2002-05-22 2007-05-01 Smithkline Beecham Corp 3'-[(2Z)-[1-(3,4- dimethylphenyl)-1,5-dihydro-3-methyl-5-oxo-4H-pyrazol-4-ylidene]hydrazino]-2'-hydroxy-[1,1'-biphenyl]-3-carboxylic acid bis-(monoethanolamine)
EP2387998A1 (en) * 2003-04-29 2011-11-23 Glaxosmithkline LLC Methods for treating degenerative diseases/injuries
DE602004019685D1 (de) 2003-12-26 2009-04-09 Allergan Inc DISUBSTITUIERTE CHALCOGENOXIME MIT ANTAGONISTISCHER WIRKUNG AM RAR(Gamma)-RETINOIDREZEPTOR
JP4518819B2 (ja) * 2004-03-17 2010-08-04 富士フイルム株式会社 アゾ化合物
AU2005314788B2 (en) * 2004-12-14 2011-09-22 Nissan Chemical Industries, Ltd. Amide compound and thrombopoietin receptor activator
JP2009511603A (ja) * 2005-10-13 2009-03-19 スミスクライン・ビーチャム・コーポレイション 貯蔵中の血小板の有効性を維持する方法
CA2630234A1 (en) * 2005-11-23 2007-05-31 Ligand Pharmaceuticals Inc. Thrombopoietin activity modulating compounds and methods

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JP5441269B2 (ja) 2014-03-12
BRPI0907234B1 (pt) 2021-08-10
JP2011509263A (ja) 2011-03-24
PT2236500E (pt) 2015-04-07
RU2010127786A (ru) 2012-02-20
CA2711535C (en) 2015-12-15
BRPI0907234A2 (pt) 2020-08-04
KR20100120141A (ko) 2010-11-12
ES2533366T3 (es) 2015-04-09
CN101679286A (zh) 2010-03-24
US20100316601A1 (en) 2010-12-16
RU2488582C2 (ru) 2013-07-27
WO2009092276A1 (zh) 2009-07-30
EP2236500B1 (en) 2014-12-24
HK1134818A1 (en) 2010-05-14
AU2009207966A1 (en) 2009-07-30
MX2010007553A (es) 2010-10-04
EP2236500A1 (en) 2010-10-06
CA2711535A1 (en) 2009-07-30
CN101481352A (zh) 2009-07-15
EP2236500A4 (en) 2012-08-22
CN101679286B (zh) 2011-06-08
UA101172C2 (ru) 2013-03-11
US20130123507A1 (en) 2013-05-16
AU2009207966B2 (en) 2013-03-21
US8367710B2 (en) 2013-02-05
ZA201004794B (en) 2011-09-28

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