CA2852771C - Process for preparing quinoline derivatives - Google Patents

Process for preparing quinoline derivatives Download PDF

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Publication number
CA2852771C
CA2852771C CA2852771A CA2852771A CA2852771C CA 2852771 C CA2852771 C CA 2852771C CA 2852771 A CA2852771 A CA 2852771A CA 2852771 A CA2852771 A CA 2852771A CA 2852771 C CA2852771 C CA 2852771C
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Canada
Prior art keywords
compound
mixture
acid
formula
img
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CA2852771A
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English (en)
French (fr)
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CA2852771A1 (en
Inventor
Jo Ann Wilson
Sriram Naganathan
Matthew Pfeiffer
Neil G. Andersen
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Exelixis Inc
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Publication of CA2852771A1 publication Critical patent/CA2852771A1/en
Application granted granted Critical
Publication of CA2852771C publication Critical patent/CA2852771C/en
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D215/20—Oxygen atoms
    • C07D215/22—Oxygen atoms attached in position 2 or 4
    • C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/57—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C233/58—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/57—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C233/59—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
    • C07D239/88—Oxygen atoms
    • C07D239/90—Oxygen atoms with acyclic radicals attached in position 2 or 3

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Quinoline Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
CA2852771A 2011-10-20 2012-10-22 Process for preparing quinoline derivatives Active CA2852771C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201161549312P 2011-10-20 2011-10-20
US61/549,312 2011-10-20
PCT/US2012/061320 WO2013059788A1 (en) 2011-10-20 2012-10-22 Process for preparing quinoline derivatives

Publications (2)

Publication Number Publication Date
CA2852771A1 CA2852771A1 (en) 2013-04-25
CA2852771C true CA2852771C (en) 2019-11-26

Family

ID=47146705

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2852771A Active CA2852771C (en) 2011-10-20 2012-10-22 Process for preparing quinoline derivatives

Country Status (23)

Country Link
US (3) US9365516B2 (https=)
EP (1) EP2768796B1 (https=)
JP (2) JP6208140B2 (https=)
KR (1) KR102075371B1 (https=)
CN (2) CN104395284A (https=)
AR (1) AR088483A1 (https=)
AU (2) AU2012325768B2 (https=)
BR (1) BR112014009302B1 (https=)
CA (1) CA2852771C (https=)
DK (1) DK2768796T3 (https=)
EA (1) EA031485B1 (https=)
ES (1) ES2765013T3 (https=)
GE (1) GEP20207110B (https=)
HU (1) HUE048023T2 (https=)
IL (1) IL232139A (https=)
IN (1) IN2014CN02971A (https=)
MX (1) MX343288B (https=)
PL (1) PL2768796T3 (https=)
PT (1) PT2768796T (https=)
TW (2) TWI642650B (https=)
UA (1) UA116876C2 (https=)
WO (1) WO2013059788A1 (https=)
ZA (1) ZA201402579B (https=)

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EP2593090B1 (en) 2010-07-16 2021-10-13 Exelixis, Inc. C-met modulator pharmaceutical compositions
CA2812750C (en) 2010-09-27 2020-10-06 Exelixis, Inc. Dual inhibitors of met and vegf for the treatment of castration-resistant prostate cancer and osteoblastic bone metastases
JP2014505109A (ja) 2011-02-10 2014-02-27 エクセリクシス， インク． キノリン化合物およびそのような化合物を含有する医薬組成物の調製方法
US20120252840A1 (en) 2011-04-04 2012-10-04 Exelixis, Inc. Method of Treating Cancer
KR20140025496A (ko) 2011-05-02 2014-03-04 엑셀리시스, 인코포레이티드 암 및 뼈 암 통증의 치료방법
GEP201606523B (en) 2011-09-22 2016-08-10 Exelixis Inc Method for treating osteoporosis
DK2768796T3 (da) * 2011-10-20 2020-02-24 Exelixis Inc Fremgangsmåde til fremstilling af quinolin-derivater
JP2015515988A (ja) 2012-05-02 2015-06-04 エクセリクシス， インク． 溶骨性骨転移を治療するためのｍｅｔ−ｖｅｇｆ二重調節剤
AU2014232714B2 (en) 2013-03-15 2018-07-19 Exelixis, Inc. Metabolites of N-(4-{[6,7-bis(methyloxy)quinolin-4-yl]oxy}phenyl)-n'-(4-fluorophenyl) cyclopropane-1,1-dicarboxamide
EP2981263B1 (en) 2013-04-04 2022-06-29 Exelixis, Inc. Cabozantinib dosage form and use in the treatment of cancer
CN104649969B (zh) * 2013-11-22 2019-02-12 广东东阳光药业有限公司 一种替尼类药物的盐及其制备方法
KR102354963B1 (ko) 2014-02-14 2022-01-21 엑셀리시스, 인코포레이티드 N-｛4-[(6,7-다이메톡시퀴놀린-4-일)옥시]페닐｝-n'-(4-플루오로페닐) 사이클로프로판-1,1-다이카복스아마이드의 결정질 고체 형태, 제조 방법 및 사용 방법
EA201691850A1 (ru) 2014-03-17 2016-12-30 Экселиксис, Инк. Дозирование составов, содержащих кабозантиниб
CN104788372B (zh) * 2014-07-25 2018-01-30 上海圣考医药科技有限公司 一种氘代卡博替尼衍生物、其制备方法、应用及其中间体
ES2929888T3 (es) 2014-07-31 2022-12-02 Exelixis Inc Procedimiento para preparar cabozantinib marcado con flúor 18 y sus análogos
BR112017002318A2 (pt) 2014-08-05 2018-07-17 Exelixis, Inc. combinações de fármacos para tratar mieloma múltiplo.
CN108026035B (zh) * 2015-09-02 2021-03-30 陈昆锋 具有蛋白酪氨酸磷酸酶shp-1激动剂活性的化合物
RU2748549C2 (ru) 2016-04-15 2021-05-26 Экселиксис, Инк. Способ лечения почечно-клеточного рака с использованием n-(4-(6,7-диметоксихинолин-4-илокси)фенил)-n'-(4-фторфенил)циклопропан-1,1-дикарбоксамида, (2s)-гидроксибутандиоата
CN109836382B (zh) * 2017-11-29 2021-11-05 江苏豪森药业集团有限公司 苹果酸卡博替尼及其中间体的制备方法
UA128476C2 (uk) 2018-01-26 2024-07-24 Екселіксіс, Інк. Сполуки для лікування кіназозалежних розладів
CN113292537B (zh) 2018-06-15 2024-04-05 汉达癌症医药责任有限公司 激酶抑制剂的盐类及其组合物
TWI887405B (zh) 2020-04-30 2025-06-21 美商艾克塞里克斯公司 製備激酶抑制劑之方法
CN112142619B (zh) * 2020-10-20 2023-01-10 浙江工业大学 一种1,1-环丙烷二羧酸酰胺类化合物及其制备方法和应用
US20240190825A1 (en) * 2021-03-24 2024-06-13 Biocon Limited Process for preparation of cabozantinib
AU2023384196A1 (en) * 2022-11-25 2025-06-12 Msn Laboratories Private Limited, R&D Center Crystalline forms of n-(4-(6,7-dimethoxyquinolin-4-yloxy)phenyl)-n'-(4-fluorophenyl) cyclopropane-1,1-dicarboxamide fumarate and process for its preparation
TW202444365A (zh) 2023-01-31 2024-11-16 漢達生技醫藥股份有限公司 改良之卡博替尼組合物及其使用方法

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PT2213661E (pt) 2003-09-26 2011-12-15 Exelixis Inc Moduladores de c-met e métodos de uso
CA2572331A1 (en) * 2004-07-02 2006-02-09 Exelixis, Inc. C-met modulators and method of use
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WO2008076415A1 (en) 2006-12-14 2008-06-26 Exelixis, Inc. Methods of using mek inhibitors
UY31800A (es) 2008-05-05 2009-11-10 Smithkline Beckman Corp Metodo de tratamiento de cancer usando un inhibidor de cmet y axl y un inhibidor de erbb
US8445509B2 (en) * 2008-05-08 2013-05-21 Takeda Pharmaceutical Company Limited Fused heterocyclic derivatives and use thereof
UY32142A (es) * 2008-09-26 2010-05-31 Smithkline Beckman Corp Preparación de una quinoliniloxidifenilciclopropanodicarboxamida
US20130197230A1 (en) * 2008-11-13 2013-08-01 Jo Ann Wilson Methods of preparing quinoline derivatives
WO2010065838A1 (en) 2008-12-04 2010-06-10 Exelixis, Inc. Methods of preparing quinoline derivatives
SG173014A1 (en) 2009-01-16 2011-08-29 Exelixis Inc Malate salt of n- (4- { [ 6, 7-bis (methyloxy) quin0lin-4-yl] oxy}phenyl)-n' - (4 -fluorophenyl) cyclopropane-1,1-dicarboxamide, and crystalline forms therof for the treatment of cancer
JP2012533570A (ja) 2009-07-17 2012-12-27 エグゼリクシス， インコーポレイテッド Ｎ−［３−フルオロ−４−（｛６−（メチルオキシ）−７−［（３−モルホリン−４−イルプロピル）オキシ］−キノリン−４−イル｝オキシ）フェニル］−ｎ’−（４−フルオロフェニル）シクロプロパン−１，１−ジカルボキサミドの結晶形
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EP2593090B1 (en) 2010-07-16 2021-10-13 Exelixis, Inc. C-met modulator pharmaceutical compositions
EP2593091A1 (en) 2010-07-16 2013-05-22 Exelixis, Inc. C-met modulator pharmaceutical compositions
EP2621483A1 (en) 2010-09-27 2013-08-07 Exelixis, Inc. Dual inhibitors of met and vegf for the treatment of castration resistant prostate cancer and osteoblastic bone metastases
CA2812750C (en) 2010-09-27 2020-10-06 Exelixis, Inc. Dual inhibitors of met and vegf for the treatment of castration-resistant prostate cancer and osteoblastic bone metastases
AU2011307306A1 (en) 2010-09-27 2013-05-02 Exelixis, Inc. Dual inhibitors of MET and VEGF for the treatment of castration resistant prostate cancer and osteoblastic bone metastases
WO2012071321A1 (en) 2010-11-22 2012-05-31 Glaxosmithkline Llc Method of treating cancer
JP2014505109A (ja) 2011-02-10 2014-02-27 エクセリクシス， インク． キノリン化合物およびそのような化合物を含有する医薬組成物の調製方法
US20120252840A1 (en) 2011-04-04 2012-10-04 Exelixis, Inc. Method of Treating Cancer
KR20140025496A (ko) 2011-05-02 2014-03-04 엑셀리시스, 인코포레이티드 암 및 뼈 암 통증의 치료방법
TW201306842A (zh) 2011-06-15 2013-02-16 Exelixis Inc 使用ｐｉ３ｋ／ｍｔｏｒ吡啶並嘧啶酮抑制劑及苯達莫司汀及／或利妥昔單抗治療惡性血液疾病之組合療法
GEP201606523B (en) 2011-09-22 2016-08-10 Exelixis Inc Method for treating osteoporosis
DK2768796T3 (da) * 2011-10-20 2020-02-24 Exelixis Inc Fremgangsmåde til fremstilling af quinolin-derivater
JP2014532766A (ja) 2011-11-08 2014-12-08 エクセリクシス， インク． 癌を治療する、ｍｅｔ及びｖｅｇｆの二重阻害剤
JP2015515988A (ja) 2012-05-02 2015-06-04 エクセリクシス， インク． 溶骨性骨転移を治療するためのｍｅｔ−ｖｅｇｆ二重調節剤
CN114129566A (zh) 2012-09-07 2022-03-04 埃克塞里艾克西斯公司 用于治疗肺腺癌的met、vegfr和ret的抑制剂

Also Published As

Publication number Publication date
HK1201517A1 (en) 2015-09-04
JP2017222648A (ja) 2017-12-21
GEP20207110B (en) 2020-05-25
IN2014CN02971A (https=) 2015-07-03
EA201490831A1 (ru) 2014-09-30
AU2012325768B2 (en) 2017-08-10
US20160229805A1 (en) 2016-08-11
KR102075371B1 (ko) 2020-02-10
GEAP201913471A (en) 2019-10-25
ES2765013T3 (es) 2020-06-05
EP2768796B1 (en) 2019-11-20
CA2852771A1 (en) 2013-04-25
PT2768796T (pt) 2020-02-21
TWI642650B (zh) 2018-12-01
BR112014009302A2 (pt) 2017-05-23
IL232139A0 (en) 2014-05-28
PL2768796T3 (pl) 2020-05-18
EP2768796A1 (en) 2014-08-27
TW201731812A (zh) 2017-09-16
WO2013059788A1 (en) 2013-04-25
HUE048023T2 (hu) 2020-05-28
ZA201402579B (en) 2015-03-25
AU2017254982A1 (en) 2017-11-23
TW201321342A (zh) 2013-06-01
JP2014530880A (ja) 2014-11-20
CN104395284A (zh) 2015-03-04
JP6208140B2 (ja) 2017-10-04
UA116876C2 (uk) 2018-05-25
EA031485B1 (ru) 2019-01-31
MX2014004583A (es) 2014-10-06
US9365516B2 (en) 2016-06-14
CN110511158A (zh) 2019-11-29
TWI619694B (zh) 2018-04-01
AR088483A1 (es) 2014-06-11
NZ624328A (en) 2016-10-28
US9969692B2 (en) 2018-05-15
NZ723880A (en) 2018-03-23
DK2768796T3 (da) 2020-02-24
AU2012325768A1 (en) 2014-05-22
US20140256938A1 (en) 2014-09-11
IL232139A (en) 2017-11-30
KR20140088874A (ko) 2014-07-11
MX343288B (es) 2016-11-01
BR112014009302B1 (pt) 2020-04-28
US20180230100A1 (en) 2018-08-16

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