PT2479174T - Derivados de 6-aminoquinazolina ou 3-cianoquinolina, métodos de preparação e utilizações farmacêuticas dos mesmos - Google Patents

Derivados de 6-aminoquinazolina ou 3-cianoquinolina, métodos de preparação e utilizações farmacêuticas dos mesmos

Info

Publication number
PT2479174T
PT2479174T PT108148677T PT10814867T PT2479174T PT 2479174 T PT2479174 T PT 2479174T PT 108148677 T PT108148677 T PT 108148677T PT 10814867 T PT10814867 T PT 10814867T PT 2479174 T PT2479174 T PT 2479174T
Authority
PT
Portugal
Prior art keywords
preparation methods
quinoline derivatives
pharmaceutical uses
amino quinazoline
cyano quinoline
Prior art date
Application number
PT108148677T
Other languages
English (en)
Inventor
Li Xin
Wang Bin
Cho Tang Peng
Wang Jun
Chen Lijun
Original Assignee
Jiangsu Hengrui Medicine Co
Shanghai hengrui pharmaceutical co ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Jiangsu Hengrui Medicine Co, Shanghai hengrui pharmaceutical co ltd filed Critical Jiangsu Hengrui Medicine Co
Publication of PT2479174T publication Critical patent/PT2479174T/pt

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/472—Non-condensed isoquinolines, e.g. papaverine
    • A61K31/4725—Non-condensed isoquinolines, e.g. papaverine containing further heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/576—Six-membered rings
    • C07F9/60—Quinoline or hydrogenated quinoline ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
    • C07F9/6509—Six-membered rings
    • C07F9/6512—Six-membered rings having the nitrogen atoms in positions 1 and 3
    • C07F9/65128—Six-membered rings having the nitrogen atoms in positions 1 and 3 condensed with carbocyclic rings or carbocyclic ring systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Molecular Biology (AREA)
  • Epidemiology (AREA)
  • Biochemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
PT108148677T 2009-09-14 2010-08-26 Derivados de 6-aminoquinazolina ou 3-cianoquinolina, métodos de preparação e utilizações farmacêuticas dos mesmos PT2479174T (pt)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN2009101958233A CN102020639A (zh) 2009-09-14 2009-09-14 6-氨基喹唑啉或3-氰基喹啉类衍生物、其制备方法及其在医药上的应用

Publications (1)

Publication Number Publication Date
PT2479174T true PT2479174T (pt) 2017-11-20

Family

ID=43731939

Family Applications (1)

Application Number Title Priority Date Filing Date
PT108148677T PT2479174T (pt) 2009-09-14 2010-08-26 Derivados de 6-aminoquinazolina ou 3-cianoquinolina, métodos de preparação e utilizações farmacêuticas dos mesmos

Country Status (20)

Country Link
US (2) US8901140B2 (pt)
EP (1) EP2479174B1 (pt)
JP (1) JP5684811B2 (pt)
KR (1) KR101738191B1 (pt)
CN (2) CN102020639A (pt)
AU (1) AU2010292790B2 (pt)
BR (1) BR112012005760A2 (pt)
CA (1) CA2774099C (pt)
DK (1) DK2479174T3 (pt)
ES (1) ES2647829T3 (pt)
HR (1) HRP20171748T1 (pt)
HU (1) HUE035873T2 (pt)
LT (1) LT2479174T (pt)
MX (1) MX2012002875A (pt)
NO (1) NO2479174T3 (pt)
PL (1) PL2479174T3 (pt)
PT (1) PT2479174T (pt)
RU (1) RU2536102C2 (pt)
SI (1) SI2479174T1 (pt)
WO (1) WO2011029265A1 (pt)

Families Citing this family (38)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102020639A (zh) 2009-09-14 2011-04-20 上海恒瑞医药有限公司 6-氨基喹唑啉或3-氰基喹啉类衍生物、其制备方法及其在医药上的应用
CN102675287A (zh) * 2011-03-11 2012-09-19 江苏恒瑞医药股份有限公司 (e)-n-[4-[[3-氯-4-(2-吡啶基甲氧基)苯基]氨基]-3-氰基-7-乙氧基-6-喹啉基]-3-[(2r)-1-甲基吡咯烷-2-基]丙-2-烯酰胺的可药用的盐、其制备方法及其在医药上的应用
CN103717590B (zh) * 2011-05-17 2016-05-11 江苏康缘药业股份有限公司 喹唑啉-7-醚化合物及使用方法
CN102898386B (zh) * 2011-07-27 2015-07-29 上海医药集团股份有限公司 喹唑啉衍生物、其制备方法、中间体、组合物及其应用
CN103987700B (zh) * 2012-03-09 2016-08-31 江苏豪森药业集团有限公司 4-喹唑啉胺类衍生物及其用途
CN103539783A (zh) * 2012-07-12 2014-01-29 江苏恒瑞医药股份有限公司 一种酪氨酸激酶抑制剂的二马来酸盐的i型结晶及制备方法
CN103588755B (zh) * 2012-08-17 2016-06-22 正大天晴药业集团股份有限公司 Neratinib的制备方法
CN103965120B (zh) * 2013-01-25 2016-08-17 上海医药集团股份有限公司 喹啉及喹唑啉衍生物、制备方法、中间体、组合物及应用
TWI609012B (zh) 2013-04-28 2017-12-21 廣東東陽光藥業有限公司 氨基喹唑啉類衍生物及其鹽和使用方法
JP6342001B2 (ja) * 2013-12-12 2018-06-13 天津和美奥康医薬科技有限公司 キナゾリン誘導体
CN106068262B (zh) * 2014-04-11 2019-10-29 海思科医药集团股份有限公司 喹唑啉衍生物及其制备方法和在医药上的应用
DK3378479T3 (da) * 2016-01-27 2020-08-03 Jiangsu Hengrui Medicine Co Fremgangsmåde til forberedelse af farmakologisk sammensætning, der omfatter qionolinderivat eller salt deraf
MX382054B (es) * 2016-01-27 2025-03-13 Jiangsu Hengrui Medicine Co Composición farmacéutica que comprende derivado de quinolina o sal del mismo.
WO2017129094A1 (zh) * 2016-01-28 2017-08-03 江苏恒瑞医药股份有限公司 一种egfr/her2受体酪氨酸激酶抑制剂在制备治疗her2突变癌症药物中的用途
CN105777604A (zh) * 2016-04-14 2016-07-20 上海凯宝药业股份有限公司 一种n-甲基-反式-4-羟基-l-脯氨酸晶体化合物及其制备方法
BR112018071617A2 (pt) * 2016-04-28 2019-02-19 Jiangsu Hengrui Medicine Co., Ltd. método para preparar inibidor de tirosina quinase e derivado do mesmo
CN106008471B (zh) * 2016-05-25 2019-09-03 江苏医诺万细胞诊疗有限公司 一种喹唑啉类化合物的合成方法
TW201813644A (zh) * 2016-09-23 2018-04-16 江蘇恆瑞醫藥股份有限公司 酪胺酸激酶抑制劑在製備治療癌症藥物中的用途
KR102355955B1 (ko) * 2016-09-23 2022-01-25 상하이 파마슈티컬스 홀딩 컴퍼니 리미티드 퀴나졸린 유도체의 염, 이의 제조 방법 및 응용
CN106565692A (zh) * 2016-11-03 2017-04-19 常茂生物化学工程股份有限公司 一种阿法替尼合成工艺的改进方法
TW201827050A (zh) * 2017-01-22 2018-08-01 大陸商江蘇恆瑞醫藥股份有限公司 Egfr/her2抑制劑聯合嘧啶類抗代謝藥物的用途
CN109963846A (zh) * 2017-08-07 2019-07-02 江苏恒瑞医药股份有限公司 一种酪氨酸激酶抑制剂的二马来酸盐的晶型及其制备方法
CN109422755B (zh) * 2017-09-01 2023-07-04 上海医药集团股份有限公司 一种含氮杂环化合物、制备方法、中间体、组合物和应用
US11407734B2 (en) 2017-10-18 2022-08-09 Jiangsu Hengrui Medicine Co., Ltd. Preparation method for tyrosine kinase inhibitor and intermediate thereof
EP3701948A4 (en) 2017-10-24 2021-08-25 Jiangsu Hengrui Medicine Co., Ltd. PHARMACEUTICAL COMPOSITION WITH QUINOLINE DERIVATIVE
CN110913894B (zh) * 2017-10-26 2023-03-10 江苏恒瑞医药股份有限公司 抗csf-1r抗体、其抗原结合片段及其医药用途
CN108314639B (zh) * 2018-05-09 2019-04-30 山东铂源药业有限公司 化合物(e)-3-(1-甲基吡咯烷-2-基)-丙烯酸盐酸盐及合成方法
CN110840892A (zh) * 2018-08-21 2020-02-28 江苏恒瑞医药股份有限公司 酪氨酸激酶抑制剂与cdk4/6抑制剂联合在制备预防或治疗肿瘤疾病的药物中的用途
CN110960529A (zh) * 2018-09-30 2020-04-07 江苏恒瑞医药股份有限公司 一种降低了毒性杂质含量的酪氨酸激酶抑制剂的原料药
WO2020083188A1 (zh) 2018-10-22 2020-04-30 江苏恒瑞医药股份有限公司 一种酪氨酸激酶抑制剂的一马来酸盐的晶型及其制备方法
CA3124330A1 (en) 2018-12-21 2020-06-25 Daiichi Sankyo Company, Limited Combination of antibody-drug conjugate and kinase inhibitor
CN112279838B (zh) 2020-10-29 2021-07-13 苏州富士莱医药股份有限公司 一种吡咯替尼的制备方法
CN112694439B (zh) * 2020-12-31 2022-08-30 河南省医药科学研究院 苯基丙烯酰胺基喹啉类衍生物及其制备方法和用途
CN112625025B (zh) * 2020-12-31 2022-03-29 河南省医药科学研究院 吡啶基取代的喹啉类衍生物及其制备方法和用途
CN112759583B (zh) * 2020-12-31 2022-10-11 河南省医药科学研究院 包含呋喃基的喹啉类衍生物及其制备方法和用途
KR20230156767A (ko) * 2021-03-19 2023-11-14 베이징 사이텍-엠큐 파마슈티컬즈 리미티드 퀴나졸린계 화합물, 조성물 및 퀴나졸린계 화합물의 적용
WO2023061472A1 (zh) * 2021-10-14 2023-04-20 江苏恒瑞医药股份有限公司 抗her2抗体药物偶联物和酪氨酸激酶抑制剂联合在制备治疗肿瘤的药物中的用途
EP4682143A1 (en) * 2023-03-10 2026-01-21 Convalife Pharmaceuticals Co., Ltd. Pharmaceutical composition containing egfr inhibitor, and preparation method therefor and use thereof

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
UA73073C2 (uk) * 1997-04-03 2005-06-15 Уайт Холдінгз Корпорейшн Заміщені 3-ціанохіноліни, спосіб їх одержання та фармацевтична композиція
HUP0103520A3 (en) 1998-09-29 2003-01-28 Wyeth Holdings Corp Madison Substituted 3-cyanoquinolines as protein tyrosine kinases inhibitors and pharmaceutical compositions containing them
CA2403152C (en) * 2000-04-08 2008-10-28 Boehringer Ingelheim Pharma Kg Bicyclic heterocycles, pharmaceutical compositions containing these compounds, their use and processes for preparing them
US7019012B2 (en) 2000-12-20 2006-03-28 Boehringer Ingelheim International Pharma Gmbh & Co. Kg Quinazoline derivatives and pharmaceutical compositions containing them
US20040044014A1 (en) * 2002-04-19 2004-03-04 Boehringer Ingelheim Pharma Gmbh & Co. Kg Bicyclic heterocycles, pharmaceutical compositions containing these compounds, their use and processes for the preparation thereof
DE10217689A1 (de) 2002-04-19 2003-11-13 Boehringer Ingelheim Pharma Bicyclische Heterocyclen, diese Verbindungen enthaltende Arzneimittel, ihre Verwendung und Verfahren zu ihrer Herstellung
DE10307165A1 (de) * 2003-02-20 2004-09-02 Boehringer Ingelheim Pharma Gmbh & Co. Kg Bicyclische Heterocyclen, diese Verbindungen enthaltende Arzneimittel, ihre Verwendung und Verfahren zu ihrer Herstellung
US7399865B2 (en) * 2003-09-15 2008-07-15 Wyeth Protein tyrosine kinase enzyme inhibitors
KR100832594B1 (ko) 2005-11-08 2008-05-27 한미약품 주식회사 다중저해제로서의 퀴나졸린 유도체 및 이의 제조방법
CN101824029A (zh) * 2009-03-05 2010-09-08 厦门艾德生物医药科技有限公司 酪氨酸激酶不可逆抑制剂、其药物组合物及其用途
CN102020639A (zh) 2009-09-14 2011-04-20 上海恒瑞医药有限公司 6-氨基喹唑啉或3-氰基喹啉类衍生物、其制备方法及其在医药上的应用

Also Published As

Publication number Publication date
CA2774099C (en) 2017-07-04
ES2647829T3 (es) 2017-12-26
US20120165352A1 (en) 2012-06-28
HUE035873T2 (en) 2018-05-28
EP2479174A4 (en) 2013-04-17
KR20120081142A (ko) 2012-07-18
WO2011029265A1 (zh) 2011-03-17
US20150126550A1 (en) 2015-05-07
RU2536102C2 (ru) 2014-12-20
BR112012005760A2 (pt) 2016-02-16
US9358227B2 (en) 2016-06-07
PL2479174T3 (pl) 2018-02-28
SI2479174T1 (sl) 2017-12-29
RU2012110882A (ru) 2013-11-10
AU2010292790B2 (en) 2015-03-26
EP2479174A1 (en) 2012-07-25
KR101738191B1 (ko) 2017-05-19
JP5684811B2 (ja) 2015-03-18
HRP20171748T1 (hr) 2017-12-29
AU2010292790A1 (en) 2012-05-10
US8901140B2 (en) 2014-12-02
LT2479174T (lt) 2017-11-27
EP2479174B1 (en) 2017-10-18
DK2479174T3 (da) 2017-11-27
MX2012002875A (es) 2012-04-20
CA2774099A1 (en) 2011-03-17
NO2479174T3 (pt) 2018-03-17
CN102471312A (zh) 2012-05-23
HK1163081A1 (en) 2012-09-07
JP2013504521A (ja) 2013-02-07
CN102471312B (zh) 2014-06-18
CN102020639A (zh) 2011-04-20

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