JP6389238B2 - Ｎ−（４−｛［６，７−ビス（メンチルオキシ）キノリン−４−イル］オキシ｝フェニル）−ｎ’−（４−フルオロフェニル）サイクロプロペイン−１，１−ジカルボキシアミドのメタボライト - Google Patents

Ｎ−（４−｛［６，７−ビス（メンチルオキシ）キノリン−４−イル］オキシ｝フェニル）−ｎ’−（４−フルオロフェニル）サイクロプロペイン−１，１−ジカルボキシアミドのメタボライト Download PDF

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JP6389238B2
JP6389238B2 JP2016503412A JP2016503412A JP6389238B2 JP 6389238 B2 JP6389238 B2 JP 6389238B2 JP 2016503412 A JP2016503412 A JP 2016503412A JP 2016503412 A JP2016503412 A JP 2016503412A JP 6389238 B2 JP6389238 B2 JP 6389238B2
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metabolite
pharmaceutically acceptable
acceptable salt
cabozantinib
compound
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JP2016516074A5 (enExample
JP2016516074A (ja
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ダナ ティー． アフタブ，
ダナ ティー． アフタブ，
スリラム ナガナサン，
スリラム ナガナサン，
ウェイ シュー，
ウェイ シュー，
スティーブン レイシー，
スティーブン レイシー，
リン グウェン，
リン グウェン，
Original Assignee
エグゼリクシス， インコーポレイテッド
エグゼリクシス， インコーポレイテッド
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    • 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
    • C07C233/60—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 singly-bound oxygen atoms
    • 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
    • C07C305/00—Esters of sulfuric acids
    • C07C305/22—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to carbon atoms of six-membered aromatic rings
    • C07C305/24—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to carbon atoms of six-membered aromatic rings of non-condensed six-membered aromatic rings
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/58—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems with hetero atoms directly attached to the ring nitrogen atom
    • C07D215/60—N-oxides
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/483—Physical analysis of biological material
    • G01N33/487—Physical analysis of biological material of liquid biological material
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N2570/00—Omics, e.g. proteomics, glycomics or lipidomics; Methods of analysis focusing on the entire complement of classes of biological molecules or subsets thereof, i.e. focusing on proteomes, glycomes or lipidomes

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biomedical Technology (AREA)
  • Physics & Mathematics (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Biophysics (AREA)
  • Pathology (AREA)
  • Immunology (AREA)
  • General Physics & Mathematics (AREA)
  • Biochemistry (AREA)
  • Analytical Chemistry (AREA)
  • Food Science & Technology (AREA)
  • Urology & Nephrology (AREA)
  • Hematology (AREA)
  • Molecular Biology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Epidemiology (AREA)
  • Pain & Pain Management (AREA)
  • Quinoline Compounds (AREA)
  • Saccharide Compounds (AREA)
JP2016503412A 2013-03-15 2014-03-17 Ｎ−（４−｛［６，７−ビス（メンチルオキシ）キノリン−４−イル］オキシ｝フェニル）−ｎ’−（４−フルオロフェニル）サイクロプロペイン−１，１−ジカルボキシアミドのメタボライト Active JP6389238B2 (ja)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201361792413P 2013-03-15 2013-03-15
US61/792,413 2013-03-15
PCT/US2014/030524 WO2014145715A1 (en) 2013-03-15 2014-03-17 Metabolites of n-(4-{[6,7-bis(methyloxy)quinolin-4-yl]oxy}phenyl)-n'-(4-fluorophenyl) cyclopropane-1,1-dicarboxamide

Publications (3)

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JP2016516074A JP2016516074A (ja) 2016-06-02
JP2016516074A5 JP2016516074A5 (enExample) 2017-04-20
JP6389238B2 true JP6389238B2 (ja) 2018-09-12

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US (4) US10273211B2 (enExample)
EP (1) EP2970126B1 (enExample)
JP (1) JP6389238B2 (enExample)
KR (1) KR102276348B1 (enExample)
CN (1) CN105121412B (enExample)
AU (2) AU2014232714B2 (enExample)
BR (1) BR112015023109A2 (enExample)
CA (1) CA2907334C (enExample)
EA (1) EA033786B1 (enExample)
ES (1) ES2729626T3 (enExample)
GE (1) GEP20196995B (enExample)
IL (1) IL241577B (enExample)
MX (1) MX366003B (enExample)
NZ (1) NZ712330A (enExample)
UA (1) UA119321C2 (enExample)
WO (1) WO2014145715A1 (enExample)
ZA (1) ZA201506842B (enExample)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MX352926B (es) 2010-09-27 2017-12-14 Exelixis Inc Inhibidores dobles de met y factor de crecimiento endotelial vascular (vegf) para el tratamiento de cancer de prostata resistente a la castracion y metastasis osteoblasticas en los huesos.
AR085155A1 (es) 2011-02-10 2013-09-11 Exelixis Inc Procesos para preparar compuestos de quinolina y composiciones farmaceuticas que contienen dichos compuestos
WO2013166296A1 (en) 2012-05-02 2013-11-07 Exelixis, Inc. A dual met - vegf modulator for treating osteolytic bone metastases
GEP20196995B (en) 2013-03-15 2019-07-25 Inc Exelixis 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
WO2015123639A1 (en) 2014-02-14 2015-08-20 Exelixis, Inc. Crystalline solid forms of n-{4-[(6,7-dimethoxyquinolin-4-yl)oxy]phenyl}-n'-(4-fluorophenyl) cyclopropane-1, 1-dicarboxamide, processes for making, and methods of use
US10159666B2 (en) 2014-03-17 2018-12-25 Exelixis, Inc. Dosing of cabozantinib formulations
CN106715397B (zh) * 2014-07-31 2021-07-23 埃克塞里艾克西斯公司 制备氟-18标记的卡博替尼及其类似物的方法
AU2015301097B2 (en) 2014-08-05 2021-03-04 Exelixis, Inc. Drug combinations to treat multiple myeloma
CA3020749A1 (en) 2016-04-15 2017-10-19 Exelixis, Inc. Method of treating renal cell carcinoma using n-(4-(6,7-dimethoxyquinolin-4-yloxy) phenyl)-n'-(4-fluoropheny)cyclopropane-1,1-dicarboxamide, (2s)-hydroxybutanedioate
CN107556238A (zh) * 2016-06-30 2018-01-09 深圳万乐药业有限公司 一种卡博替尼的合成方法
HRP20251184T1 (hr) 2018-01-26 2025-12-05 Exelixis, Inc. Spojevi za liječenje poremećaja ovisnih o kinazi
AU2019285066B2 (en) 2018-06-15 2024-06-13 Handa Pharmaceuticals, Inc. Kinase inhibitor salts and compositions thereof
CN110423218A (zh) * 2019-08-09 2019-11-08 新乡双鹭药业有限公司 一种苹果酸卡博替尼合成中杂质的制备方法
WO2024114710A1 (zh) * 2022-12-01 2024-06-06 江苏奥赛康药业有限公司 一种制备卡博替尼及其中间体的方法
CN120417903A (zh) 2023-01-31 2025-08-01 汉达癌症医药责任有限公司 改良的卡博替尼组合物及其使用方法

Family Cites Families (40)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SI2392564T1 (sl) 2003-09-26 2014-02-28 Exelixis, Inc. c-Met modulatorji in postopki uporabe
AU2005270068B2 (en) 2004-07-02 2012-04-19 Exelixis, Inc. C-Met modulators and method of use
EP1874759A4 (en) 2005-04-06 2009-07-15 Exelixis Inc C-MET MODULATORS MODULATORS AND METHODS OF USE
UY30183A1 (es) 2006-03-02 2007-10-31 Astrazeneca Ab Derivados de quinolina
TR201900306T4 (tr) 2006-12-14 2019-02-21 Exelixis Inc Mek inhibitörlerini kullanma yöntemleri.
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
TW201035017A (en) 2008-09-26 2010-10-01 Smithkline Beecham Corp Preparation of a quinolinyloxydiphenylcyclopropanedicarboxamide
EA019247B1 (ru) 2008-11-13 2014-02-28 Экселиксис, Инк. Способы получения хинолиновых производных
JP2012511017A (ja) 2008-12-04 2012-05-17 エグゼリクシス， インコーポレイテッド キノリン誘導体の調製方法
NZ779754A (en) 2009-01-16 2023-04-28 Exelixis Inc Malate salt of n-(4-{ [6,7-bis(methyloxy)quinolin-4-yl] oxy} phenyl)-n’-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide, and crystalline forms thereof for the treatment of cancer
AU2010274012A1 (en) 2009-07-17 2012-02-09 Exelixis, Inc. Crystalline forms of N-[3-fluoro-4-({6-(methyloxy)-7-[(3-morpholin-4-ylpropyl)oxy] -quinolin-4-yl}oxy)phenyl]-N'-(4-fluorophenyl)cyclopropane-1, 1-dicarboxamide
UA108618C2 (uk) 2009-08-07 2015-05-25 Застосування c-met-модуляторів в комбінації з темозоломідом та/або променевою терапією для лікування раку
CN102933551A (zh) 2010-03-12 2013-02-13 埃克塞里艾克西斯公司 N-[3-氟-4-({6-(甲氧基)-7-[(3-吗啉-4-基丙基)氧基]-喹啉-4-基}氧基)苯基]-n’-(4-氟苯基)环丙烷-1,1-二甲酰胺的水合结晶形式
US20120070368A1 (en) 2010-04-16 2012-03-22 Exelixis, Inc. Methods of Using C-Met Modulators
CN114209699A (zh) 2010-07-16 2022-03-22 埃克塞里艾克西斯公司 C-met调节剂药物组合物
WO2012009723A1 (en) 2010-07-16 2012-01-19 Exelixis, Inc. C-met modulator pharmaceutical compositions
CA2812744A1 (en) 2010-09-27 2012-04-05 Exelixis, Inc. Dual inhibitors of met and vegf for the treatment of castration resistant prostate cancer and osteoblastic bone metastases
MX352926B (es) 2010-09-27 2017-12-14 Exelixis Inc Inhibidores dobles de met y factor de crecimiento endotelial vascular (vegf) para el tratamiento de cancer de prostata resistente a la castracion y metastasis osteoblasticas en los huesos.
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
KR20140002711A (ko) * 2010-12-23 2014-01-08 네스텍 소시에테아노님 항체-기반 어레이를 사용한 악성 암 치료를 위한 약물 선별법
CN102093421B (zh) 2011-01-28 2014-07-02 北京康辰药业有限公司 一种含磷取代基的喹啉类化合物及其制备方法、以及含有该化合物的药物组合物及其应用
AR085155A1 (es) 2011-02-10 2013-09-11 Exelixis Inc Procesos para preparar compuestos de quinolina y composiciones farmaceuticas que contienen dichos compuestos
US20120252840A1 (en) 2011-04-04 2012-10-04 Exelixis, Inc. Method of Treating Cancer
TWI610918B (zh) 2011-05-02 2018-01-11 艾克塞里克斯公司 治療癌症及骨癌疼痛之方法
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
KR20140069133A (ko) 2011-09-22 2014-06-09 엑셀리시스, 인코포레이티드 골다공증의 치료방법
UA116876C2 (uk) 2011-10-20 2018-05-25 Екселіксіс, Інк. Спосіб одержання хінолінових похідних
BR112014011009A2 (pt) 2011-11-08 2017-06-06 Exelixis Inc inibidor duplo de met e vegf para tratar câncer
WO2013166296A1 (en) 2012-05-02 2013-11-07 Exelixis, Inc. A dual met - vegf modulator for treating osteolytic bone metastases
JP6513567B2 (ja) 2012-09-07 2019-05-15 エクセリクシス， インク． 肺腺癌の治療で使用するためのｍｅｔ、ｖｅｇｆｒ、およびｒｅｔの阻害剤
CN103664776B (zh) * 2012-09-26 2016-05-04 正大天晴药业集团股份有限公司 一种酪氨酸激酶抑制剂及其中间体的制备方法
US20140221372A1 (en) 2013-02-06 2014-08-07 GlaxoSmithKline Intellectual Property (NO 2.) Limited Method of administration and treatment
GEP20196995B (en) 2013-03-15 2019-07-25 Inc Exelixis Metabolites of n-(4-{[6,7-bis (methyloxy)quinolin-4-yl] oxy}phenyl)-n'-(4-fluorophenyl) cyclopropane-1,1-dicarboxamide
WO2014145693A1 (en) * 2013-03-15 2014-09-18 Exelixis, Inc. Metabolites of n-[3-fluoro-4-({ 6-(methyloxy)-7-[(3-morpholin-4-ylpropyl)oxy]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
MX2015014046A (es) 2013-04-04 2016-05-16 Exelixis Inc Combinaciones de farmacos para tratar cancer.
WO2015123639A1 (en) 2014-02-14 2015-08-20 Exelixis, Inc. Crystalline solid forms of n-{4-[(6,7-dimethoxyquinolin-4-yl)oxy]phenyl}-n'-(4-fluorophenyl) cyclopropane-1, 1-dicarboxamide, processes for making, and methods of use
US10159666B2 (en) 2014-03-17 2018-12-25 Exelixis, Inc. Dosing of cabozantinib formulations
CN106715397B (zh) * 2014-07-31 2021-07-23 埃克塞里艾克西斯公司 制备氟-18标记的卡博替尼及其类似物的方法

Also Published As

Publication number Publication date
US10273211B2 (en) 2019-04-30
EP2970126B1 (en) 2019-03-06
CN105121412B (zh) 2019-07-12
US20210002228A1 (en) 2021-01-07
ES2729626T3 (es) 2019-11-05
GEP20196995B (en) 2019-07-25
UA119321C2 (uk) 2019-06-10
CN105121412A (zh) 2015-12-02
US20160031818A1 (en) 2016-02-04
BR112015023109A2 (pt) 2018-05-15
NZ712330A (en) 2020-04-24
EA033786B1 (ru) 2019-11-26
HK1220447A1 (en) 2017-05-05
MX2015012490A (es) 2016-05-24
US20240287002A1 (en) 2024-08-29
AU2014232714B2 (en) 2018-07-19
JP2016516074A (ja) 2016-06-02
KR20150130376A (ko) 2015-11-23
AU2014232714A1 (en) 2015-10-08
CA2907334A1 (en) 2014-09-18
EP2970126A1 (en) 2016-01-20
EA201591756A1 (ru) 2016-02-29
ZA201506842B (en) 2017-08-30
CA2907334C (en) 2021-12-07
AU2018204666A1 (en) 2018-07-19
MX366003B (es) 2019-06-24
US20190218182A1 (en) 2019-07-18
IL241577B (en) 2019-11-28
WO2014145715A1 (en) 2014-09-18
KR102276348B1 (ko) 2021-07-12

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