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 PDFInfo
- Publication number
- 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
- Authority
- JP
- Japan
- Prior art keywords
- metabolite
- pharmaceutically acceptable
- acceptable salt
- cabozantinib
- compound
- Prior art date
- Legal status (The legal status 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 status listed.)
- Active
Links
Classifications
-
- 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
Landscapes
- 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)
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)
| Publication Number | Publication Date |
|---|---|
| JP2016516074A JP2016516074A (ja) | 2016-06-02 |
| JP2016516074A5 JP2016516074A5 (enExample) | 2017-04-20 |
| JP6389238B2 true JP6389238B2 (ja) | 2018-09-12 |
Family
ID=50631091
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016503412A Active JP6389238B2 (ja) | 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 |
Country Status (17)
| Country | Link |
|---|---|
| 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)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SI2621481T2 (sl) | 2010-09-27 | 2023-02-28 | Exelixis, Inc., | Dvojni inhibitorji MET in VEGF za zdravljenje proti kastraciji odpornega raka prostate in osteoblastnih kostnih metastaz |
| DK2673262T3 (da) | 2011-02-10 | 2022-01-24 | Exelixis Inc | Fremgangsmåder til fremstilling af quinolinforbindelser og farmaceutiske sammensætninger indeholdende sådanne forbindelser |
| WO2013166296A1 (en) | 2012-05-02 | 2013-11-07 | Exelixis, Inc. | A dual met - vegf modulator for treating osteolytic bone metastases |
| WO2014145715A1 (en) | 2013-03-15 | 2014-09-18 | Exelixis, Inc. | Metabolites of n-(4-{[6,7-bis(methyloxy)quinolin-4-yl]oxy}phenyl)-n'-(4-fluorophenyl) cyclopropane-1,1-dicarboxamide |
| US11564915B2 (en) | 2013-04-04 | 2023-01-31 | Exelixis, Inc. | Cabozantinib dosage form and use in the treatment of cancer |
| CA3181899A1 (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 |
| EA201691850A1 (ru) * | 2014-03-17 | 2016-12-30 | Экселиксис, Инк. | Дозирование составов, содержащих кабозантиниб |
| CA2956810C (en) | 2014-07-31 | 2022-10-04 | Exelixis, Inc. | Method of preparing fluorine-18 labeled cabozantinib and its analogs |
| WO2016022697A1 (en) | 2014-08-05 | 2016-02-11 | Exelixis, Inc. | Drug combinations to treat multiple myeloma |
| 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 |
| 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 |
| FI3743070T3 (fi) | 2018-01-26 | 2025-10-16 | Exelixis Inc | Yhdisteitä kinaasista riippuvaisten häiriöiden hoitoon |
| KR20210042896A (ko) | 2018-06-15 | 2021-04-20 | 한다 파마슈티칼스, 인코포레이티드 | 카이네이스 억제제 염 및 이의 조성물 |
| 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 |
| 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 |
Family Cites Families (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2210607B1 (en) | 2003-09-26 | 2011-08-17 | Exelixis Inc. | N-[3-fluoro-4-({6-(methyloxy)-7-[(3-morpholin-4-ylpropyl)oxy]quinolin-4-yl}oxy)phenyl]-N'-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide for the treatment of cancer |
| CA2572331A1 (en) | 2004-07-02 | 2006-02-09 | Exelixis, Inc. | C-met modulators and method of use |
| US20080161305A1 (en) | 2005-04-06 | 2008-07-03 | Exelixis, Inc. | C-Met Modulators and Methods of Use |
| UY30183A1 (es) | 2006-03-02 | 2007-10-31 | Astrazeneca Ab | Derivados de quinolina |
| US7999006B2 (en) | 2006-12-14 | 2011-08-16 | 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 |
| AR075084A1 (es) | 2008-09-26 | 2011-03-09 | Smithkline Beecham Corp | Metodo de preparacion de quinolinil -oxidifenil - ciclopropanodicarboxamidas e intermediarios correspondientes |
| CN102282134B (zh) | 2008-11-13 | 2015-04-01 | 埃克塞里艾克西斯公司 | 喹啉衍生物制备方法 |
| US20130030172A1 (en) | 2008-12-04 | 2013-01-31 | Exelixis, Inc. | Methods of Preparing Quinoline Derivatives |
| AU2010204619B2 (en) | 2009-01-16 | 2016-08-11 | 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 |
| EP2454238A1 (en) | 2009-07-17 | 2012-05-23 | 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 | |
| KR20130038206A (ko) | 2010-03-12 | 2013-04-17 | 엑셀리시스, 인코포레이티드 | N-〔3-플루오로-4-({6-(메틸옥시)-7-〔(3-모폴린-4-일프로필)옥시〕-퀴놀린-4-일}옥시)페닐〕-n’-(4-플루오로페닐)사이클로프로판-1,1-디카복사미드의 수화된 결정형 형태 |
| US20120070368A1 (en) | 2010-04-16 | 2012-03-22 | Exelixis, Inc. | Methods of Using C-Met Modulators |
| WO2012009723A1 (en) | 2010-07-16 | 2012-01-19 | Exelixis, Inc. | C-met modulator pharmaceutical compositions |
| KR20210014770A (ko) | 2010-07-16 | 2021-02-09 | 엑셀리시스, 인코포레이티드 | C-met 조절제 약제학적 조성물 |
| SI2621481T2 (sl) | 2010-09-27 | 2023-02-28 | Exelixis, Inc., | Dvojni inhibitorji MET in VEGF za zdravljenje proti kastraciji odpornega raka prostate in osteoblastnih kostnih metastaz |
| JP2013537918A (ja) | 2010-09-27 | 2013-10-07 | エクセリクシス, インク. | 去勢抵抗性前立腺癌および骨芽細胞骨転移の治療のためのmetおよびvegfの二元阻害薬 |
| WO2012044574A1 (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 |
| EP2643001A4 (en) | 2010-11-22 | 2014-02-19 | Glaxosmithkline Ip Dev Ltd | METHOD OF TREATING CANCER |
| MX2013007429A (es) * | 2010-12-23 | 2014-01-31 | Nestec Sa | Seleccion de farmacos para terapia de cancer maligno usando disposiciones a base de anticuerpos. |
| 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 |
| DK2673262T3 (da) | 2011-02-10 | 2022-01-24 | Exelixis Inc | Fremgangsmåder til fremstilling af quinolinforbindelser og farmaceutiske sammensætninger indeholdende sådanne forbindelser |
| 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 |
| UA115866C2 (uk) | 2011-09-22 | 2018-01-10 | Екселіксіс, Інк. | Спосіб лікування остеопорозу |
| KR102075371B1 (ko) | 2011-10-20 | 2020-02-10 | 엑셀리시스, 인코포레이티드 | 퀴놀린 유도체 제조 방법 |
| KR20140088610A (ko) | 2011-11-08 | 2014-07-10 | 엑셀리시스, 인코포레이티드 | 암을 치료하기 위한 met 및 vegf의 이중 저해제 |
| WO2013166296A1 (en) | 2012-05-02 | 2013-11-07 | Exelixis, Inc. | A dual met - vegf modulator for treating osteolytic bone metastases |
| 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 |
| 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 |
| WO2014145715A1 (en) | 2013-03-15 | 2014-09-18 | Exelixis, Inc. | 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 |
| KR20150138268A (ko) | 2013-04-04 | 2015-12-09 | 엑셀리시스, 인코포레이티드 | 암을 치료하기 위한 약물 병용요법 |
| US11564915B2 (en) | 2013-04-04 | 2023-01-31 | Exelixis, Inc. | Cabozantinib dosage form and use in the treatment of cancer |
| CA3181899A1 (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 |
| EA201691850A1 (ru) | 2014-03-17 | 2016-12-30 | Экселиксис, Инк. | Дозирование составов, содержащих кабозантиниб |
| CA2956810C (en) | 2014-07-31 | 2022-10-04 | Exelixis, Inc. | Method of preparing fluorine-18 labeled cabozantinib and its analogs |
-
2014
- 2014-03-17 WO PCT/US2014/030524 patent/WO2014145715A1/en not_active Ceased
- 2014-03-17 CN CN201480021215.XA patent/CN105121412B/zh active Active
- 2014-03-17 CA CA2907334A patent/CA2907334C/en active Active
- 2014-03-17 ES ES14721149T patent/ES2729626T3/es active Active
- 2014-03-17 GE GEAP201413960A patent/GEP20196995B/en unknown
- 2014-03-17 NZ NZ712330A patent/NZ712330A/en unknown
- 2014-03-17 MX MX2015012490A patent/MX366003B/es active IP Right Grant
- 2014-03-17 KR KR1020157027712A patent/KR102276348B1/ko active Active
- 2014-03-17 JP JP2016503412A patent/JP6389238B2/ja active Active
- 2014-03-17 EP EP14721149.4A patent/EP2970126B1/en active Active
- 2014-03-17 EA EA201591756A patent/EA033786B1/ru not_active IP Right Cessation
- 2014-03-17 UA UAA201510088A patent/UA119321C2/uk unknown
- 2014-03-17 BR BR112015023109A patent/BR112015023109A2/pt not_active Application Discontinuation
- 2014-03-17 AU AU2014232714A patent/AU2014232714B2/en active Active
- 2014-03-17 US US14/776,337 patent/US10273211B2/en active Active
-
2015
- 2015-09-10 IL IL24157715A patent/IL241577B/en active IP Right Grant
- 2015-09-15 ZA ZA2015/06842A patent/ZA201506842B/en unknown
-
2018
- 2018-06-27 AU AU2018204666A patent/AU2018204666A1/en not_active Abandoned
-
2019
- 2019-03-25 US US16/362,863 patent/US20190218182A1/en not_active Abandoned
-
2020
- 2020-09-24 US US17/031,196 patent/US20210002228A1/en not_active Abandoned
-
2024
- 2024-04-22 US US18/641,587 patent/US20240287002A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| ES2729626T3 (es) | 2019-11-05 |
| BR112015023109A2 (pt) | 2018-05-15 |
| CA2907334A1 (en) | 2014-09-18 |
| HK1220447A1 (en) | 2017-05-05 |
| US20190218182A1 (en) | 2019-07-18 |
| US20240287002A1 (en) | 2024-08-29 |
| AU2014232714A1 (en) | 2015-10-08 |
| WO2014145715A1 (en) | 2014-09-18 |
| AU2018204666A1 (en) | 2018-07-19 |
| KR20150130376A (ko) | 2015-11-23 |
| EP2970126A1 (en) | 2016-01-20 |
| JP2016516074A (ja) | 2016-06-02 |
| NZ712330A (en) | 2020-04-24 |
| US20160031818A1 (en) | 2016-02-04 |
| CN105121412B (zh) | 2019-07-12 |
| EA033786B1 (ru) | 2019-11-26 |
| US10273211B2 (en) | 2019-04-30 |
| CN105121412A (zh) | 2015-12-02 |
| IL241577B (en) | 2019-11-28 |
| EA201591756A1 (ru) | 2016-02-29 |
| US20210002228A1 (en) | 2021-01-07 |
| AU2014232714B2 (en) | 2018-07-19 |
| UA119321C2 (uk) | 2019-06-10 |
| ZA201506842B (en) | 2017-08-30 |
| GEP20196995B (en) | 2019-07-25 |
| KR102276348B1 (ko) | 2021-07-12 |
| MX2015012490A (es) | 2016-05-24 |
| MX366003B (es) | 2019-06-24 |
| EP2970126B1 (en) | 2019-03-06 |
| CA2907334C (en) | 2021-12-07 |
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