KR102075371B1 - 퀴놀린 유도체 제조 방법 - Google Patents
퀴놀린 유도체 제조 방법 Download PDFInfo
- Publication number
- KR102075371B1 KR102075371B1 KR1020147012435A KR20147012435A KR102075371B1 KR 102075371 B1 KR102075371 B1 KR 102075371B1 KR 1020147012435 A KR1020147012435 A KR 1020147012435A KR 20147012435 A KR20147012435 A KR 20147012435A KR 102075371 B1 KR102075371 B1 KR 102075371B1
- Authority
- KR
- South Korea
- Prior art keywords
- compound
- mixture
- formula
- acid
- polar aprotic
- 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.)
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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)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (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)
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 |
|---|---|
| KR20140088874A KR20140088874A (ko) | 2014-07-11 |
| KR102075371B1 true KR102075371B1 (ko) | 2020-02-10 |
Family
ID=47146705
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020147012435A Active KR102075371B1 (ko) | 2011-10-20 | 2012-10-22 | 퀴놀린 유도체 제조 방법 |
Country Status (23)
| Country | Link |
|---|---|
| US (3) | US9365516B2 (enExample) |
| EP (1) | EP2768796B1 (enExample) |
| JP (2) | JP6208140B2 (enExample) |
| KR (1) | KR102075371B1 (enExample) |
| CN (2) | CN104395284A (enExample) |
| AR (1) | AR088483A1 (enExample) |
| AU (2) | AU2012325768B2 (enExample) |
| BR (1) | BR112014009302B1 (enExample) |
| CA (1) | CA2852771C (enExample) |
| DK (1) | DK2768796T3 (enExample) |
| EA (1) | EA031485B1 (enExample) |
| ES (1) | ES2765013T3 (enExample) |
| GE (1) | GEP20207110B (enExample) |
| HU (1) | HUE048023T2 (enExample) |
| IL (1) | IL232139A (enExample) |
| IN (1) | IN2014CN02971A (enExample) |
| MX (1) | MX343288B (enExample) |
| PL (1) | PL2768796T3 (enExample) |
| PT (1) | PT2768796T (enExample) |
| TW (2) | TWI619694B (enExample) |
| UA (1) | UA116876C2 (enExample) |
| WO (1) | WO2013059788A1 (enExample) |
| ZA (1) | ZA201402579B (enExample) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2593090B1 (en) | 2010-07-16 | 2021-10-13 | Exelixis, Inc. | C-met modulator pharmaceutical compositions |
| FI2621481T4 (fi) | 2010-09-27 | 2023-01-13 | Met- ja vegf-kaksoisestäjiä kastraatioresistentin eturauhassyövän ja osteoblastisten luun etäispesäkkeiden hoitamiseen | |
| EA033513B1 (ru) | 2011-02-10 | 2019-10-31 | Exelixis Inc | Способы получения хинолиновых соединений и фармацевтических композиций, содержащих такие соединения |
| US20120252840A1 (en) | 2011-04-04 | 2012-10-04 | Exelixis, Inc. | Method of Treating Cancer |
| BR212013028314U2 (pt) | 2011-05-02 | 2015-11-03 | Exelixis Inc | método para tratar câncer e dor de câncer de osso |
| EP2758057B1 (en) | 2011-09-22 | 2017-05-31 | Exelixis, Inc. | Method for treating osteoporosis |
| PT2768796T (pt) * | 2011-10-20 | 2020-02-21 | Exelixis Inc | Processo para a preparação de derivados de quinolina |
| EP2844254A1 (en) | 2012-05-02 | 2015-03-11 | Exelixis, Inc. | A dual met - vegf modulator for treating osteolytic bone metastases |
| JP6389238B2 (ja) | 2013-03-15 | 2018-09-12 | エグゼリクシス， インコーポレイテッド | 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 |
| US11564915B2 (en) | 2013-04-04 | 2023-01-31 | 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 |
| MX384828B (es) | 2014-02-14 | 2025-03-14 | Exelixis Inc | Formas solidas cristalinas de n-{4-[(6,7-dimetoxiquinolin-4-il)oxi]fenil}-n'-(4-fluorofenil)ciclopropan-1,1-dicarboxamida, procesos para elaboracion y metodos de uso. |
| WO2015142928A1 (en) | 2014-03-17 | 2015-09-24 | Exelixis, Inc. | Dosing of cabozantinib formulations |
| 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 |
| EP3174854B1 (en) | 2014-07-31 | 2022-08-24 | Exelixis, Inc. | Method of preparing fluorine-18 labeled cabozantinib and its analogs |
| MA40457A (fr) | 2014-08-05 | 2017-06-14 | Exelixis Inc | Combinaison de médicaments pour traiter le myélome multiple |
| EP3345894B1 (en) * | 2015-09-02 | 2021-12-29 | Chen, Kuenfeng | Compound having protein tyrosine phosphatase shp-1 agonist activity |
| 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 |
| 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 |
| SG11202006921PA (en) | 2018-01-26 | 2020-08-28 | Exelixis Inc | Compounds for the treatment of kinase-dependent disorders |
| 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 |
| CA3176042A1 (en) | 2020-04-30 | 2021-11-04 | Exelixis, Inc. | Processes for the preparation of a kinase inhibitor |
| 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 |
| MX2023011292A (es) * | 2021-03-24 | 2023-11-28 | Biocon Ltd | Proceso para preparación de 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 |
| 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 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010083414A1 (en) * | 2009-01-16 | 2010-07-22 | Exelixis, Inc. | Malate salt of n- (4- { [ 6, 7-bis (methyloxy) quin0lin-4-yl] oxy}phenyl-n' - (4 -fluorophenyl) cyclopropane-1-dicarboxamide, and crystalline forms therof for the treatment of cancer |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2744997A1 (en) | 2003-09-26 | 2005-04-07 | Exelixis, Inc. | C-met modulators and method of use |
| 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 |
| CN105106199A (zh) | 2006-12-14 | 2015-12-02 | 埃克塞利希斯股份有限公司 | 使用mek抑制剂的方法 |
| 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 |
| TW201035017A (en) * | 2008-09-26 | 2010-10-01 | Smithkline Beecham Corp | Preparation of a quinolinyloxydiphenylcyclopropanedicarboxamide |
| JP5486606B2 (ja) | 2008-11-13 | 2014-05-07 | エクセリクシス， インク． | キノリン誘導体の調製方法 |
| US20130030172A1 (en) | 2008-12-04 | 2013-01-31 | Exelixis, Inc. | Methods of Preparing Quinoline Derivatives |
| KR20120051702A (ko) | 2009-07-17 | 2012-05-22 | 엑셀리시스, 인코포레이티드 | Ｎ-〔３-플루오로-４-(｛６-(메틸옥시)-７-〔(３-모르폴린-４-일프로필)옥시〕퀴놀린-４-일｝옥시)페닐〕-ｎ''-(４-플루오로페닐)시클로프로판-１,１-디카르복사미드의 결정형 |
| 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 |
| 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 |
| JP2013540759A (ja) | 2010-09-27 | 2013-11-07 | エクセリクシス， インク． | 去勢抵抗性前立腺癌および造骨性転移の治療のためのｍｅｔおよびｖｅｇｆの二元阻害薬 |
| 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 |
| FI2621481T4 (fi) | 2010-09-27 | 2023-01-13 | Met- ja vegf-kaksoisestäjiä kastraatioresistentin eturauhassyövän ja osteoblastisten luun etäispesäkkeiden hoitamiseen | |
| CN103327979A (zh) | 2010-11-22 | 2013-09-25 | 葛兰素史密斯克莱知识产权（第2号）有限公司 | 治疗癌症的方法 |
| EA033513B1 (ru) | 2011-02-10 | 2019-10-31 | Exelixis Inc | Способы получения хинолиновых соединений и фармацевтических композиций, содержащих такие соединения |
| US20120252840A1 (en) | 2011-04-04 | 2012-10-04 | Exelixis, Inc. | Method of Treating Cancer |
| BR212013028314U2 (pt) | 2011-05-02 | 2015-11-03 | Exelixis Inc | método para tratar câncer e dor de câncer de osso |
| 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 |
| EP2758057B1 (en) | 2011-09-22 | 2017-05-31 | Exelixis, Inc. | Method for treating osteoporosis |
| PT2768796T (pt) | 2011-10-20 | 2020-02-21 | Exelixis Inc | Processo para a preparação de derivados de quinolina |
| IN2014CN04067A (enExample) | 2011-11-08 | 2015-10-23 | Exelixis Inc | |
| EP2844254A1 (en) | 2012-05-02 | 2015-03-11 | Exelixis, Inc. | A dual met - vegf modulator for treating osteolytic bone metastases |
| US20150238477A1 (en) | 2012-09-07 | 2015-08-27 | Exelixis, Inc. | Method of Treating Lung Adenocarcinoma |
-
2012
- 2012-10-22 PT PT127837631T patent/PT2768796T/pt unknown
- 2012-10-22 IN IN2971CHN2014 patent/IN2014CN02971A/en unknown
- 2012-10-22 TW TW101139005A patent/TWI619694B/zh active
- 2012-10-22 AR ARP120103944 patent/AR088483A1/es not_active Application Discontinuation
- 2012-10-22 BR BR112014009302A patent/BR112014009302B1/pt active IP Right Grant
- 2012-10-22 CN CN201280054241.3A patent/CN104395284A/zh active Pending
- 2012-10-22 EP EP12783763.1A patent/EP2768796B1/en active Active
- 2012-10-22 PL PL12783763T patent/PL2768796T3/pl unknown
- 2012-10-22 GE GEAP201213471A patent/GEP20207110B/en unknown
- 2012-10-22 MX MX2014004583A patent/MX343288B/es active IP Right Grant
- 2012-10-22 CN CN201910783833.2A patent/CN110511158A/zh active Pending
- 2012-10-22 AU AU2012325768A patent/AU2012325768B2/en active Active
- 2012-10-22 DK DK12783763.1T patent/DK2768796T3/da active
- 2012-10-22 EA EA201490831A patent/EA031485B1/ru unknown
- 2012-10-22 CA CA2852771A patent/CA2852771C/en active Active
- 2012-10-22 ES ES12783763T patent/ES2765013T3/es active Active
- 2012-10-22 KR KR1020147012435A patent/KR102075371B1/ko active Active
- 2012-10-22 UA UAA201405355A patent/UA116876C2/uk unknown
- 2012-10-22 WO PCT/US2012/061320 patent/WO2013059788A1/en not_active Ceased
- 2012-10-22 HU HUE12783763A patent/HUE048023T2/hu unknown
- 2012-10-22 TW TW106121791A patent/TWI642650B/zh active
- 2012-10-22 JP JP2014537359A patent/JP6208140B2/ja active Active
- 2012-10-22 US US14/353,251 patent/US9365516B2/en active Active
-
2014
- 2014-04-09 ZA ZA2014/02579A patent/ZA201402579B/en unknown
- 2014-04-22 IL IL232139A patent/IL232139A/en active IP Right Grant
-
2016
- 2016-04-20 US US15/133,708 patent/US9969692B2/en active Active
-
2017
- 2017-06-07 JP JP2017112355A patent/JP2017222648A/ja active Pending
- 2017-11-06 AU AU2017254982A patent/AU2017254982A1/en not_active Abandoned
-
2018
- 2018-04-17 US US15/955,246 patent/US20180230100A1/en not_active Abandoned
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010083414A1 (en) * | 2009-01-16 | 2010-07-22 | Exelixis, Inc. | Malate salt of n- (4- { [ 6, 7-bis (methyloxy) quin0lin-4-yl] oxy}phenyl-n' - (4 -fluorophenyl) cyclopropane-1-dicarboxamide, and crystalline forms therof for the treatment of cancer |
Non-Patent Citations (1)
| Title |
|---|
| 논문 Bioorg. Med. Chem. Lett. (Vol. 19, 2009.10.25.)* |
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