JP2016516074A5 - - Google Patents
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- Publication number
- JP2016516074A5 JP2016516074A5 JP2016503412A JP2016503412A JP2016516074A5 JP 2016516074 A5 JP2016516074 A5 JP 2016516074A5 JP 2016503412 A JP2016503412 A JP 2016503412A JP 2016503412 A JP2016503412 A JP 2016503412A JP 2016516074 A5 JP2016516074 A5 JP 2016516074A5
- Authority
- JP
- Japan
- Prior art keywords
- pharmaceutically acceptable
- acceptable salt
- metabolite
- isolated
- item
- 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.)
- Granted
Links
- 150000003839 salts Chemical class 0.000 claims description 30
- 239000002207 metabolite Substances 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 11
- IAJILQKETJEXLJ-QTBDOELSSA-N aldehydo-D-glucuronic acid Chemical group O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-QTBDOELSSA-N 0.000 claims description 6
- ONIQOQHATWINJY-UHFFFAOYSA-N cabozantinib Chemical class C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=C1)=CC=C1NC(=O)C1(C(=O)NC=2C=CC(F)=CC=2)CC1 ONIQOQHATWINJY-UHFFFAOYSA-N 0.000 claims description 6
- 241000124008 Mammalia Species 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 4
- 210000001124 body fluid Anatomy 0.000 claims description 3
- 239000010839 body fluid Substances 0.000 claims description 3
- 201000010099 disease Diseases 0.000 claims description 3
- -1 4 - {[6,7- bis (menthyloxy) quinolin-4-yl] oxy} phenyl Chemical group 0.000 claims description 2
- 239000002176 L01XE26 - Cabozantinib Substances 0.000 claims description 2
- 230000002159 abnormal effect Effects 0.000 claims description 2
- 210000000941 bile Anatomy 0.000 claims description 2
- 229960001292 cabozantinib Drugs 0.000 claims description 2
- 230000001413 cellular effect Effects 0.000 claims description 2
- 208000035475 disorder Diseases 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 210000002381 plasma Anatomy 0.000 claims description 2
- 210000002700 urine Anatomy 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- 239000012530 fluid Substances 0.000 claims 1
- 0 COc(c(OC)cc1ncc2)cc1c2Oc(cc1)ccc1NC(C1(CC1)C(Nc(c(*)c1)ccc1F)=O)=O Chemical compound COc(c(OC)cc1ncc2)cc1c2Oc(cc1)ccc1NC(C1(CC1)C(Nc(c(*)c1)ccc1F)=O)=O 0.000 description 9
- CUMXVRCMCHLCHR-UHFFFAOYSA-N COc(c(O)cc1ncc2)cc1c2Oc(cc1)ccc1NC(C1(CC1)C(Nc(cc1)ccc1F)=O)=O Chemical compound COc(c(O)cc1ncc2)cc1c2Oc(cc1)ccc1NC(C1(CC1)C(Nc(cc1)ccc1F)=O)=O CUMXVRCMCHLCHR-UHFFFAOYSA-N 0.000 description 2
- ACPMVTQPBYQJIM-UHFFFAOYSA-N COc(c(OC)cc1ncc2)cc1c2Oc(cc1)ccc1NC(C1(CC1)C(Nc(cc1O)ccc1F)=O)=O Chemical compound COc(c(OC)cc1ncc2)cc1c2Oc(cc1)ccc1NC(C1(CC1)C(Nc(cc1O)ccc1F)=O)=O ACPMVTQPBYQJIM-UHFFFAOYSA-N 0.000 description 2
- NHMICDOYSFGBAB-UHFFFAOYSA-N COc1cc2nccc(Oc(cc3)ccc3NC(C3(CC3)C(Nc(cc3)ccc3F)=O)=O)c2cc1O Chemical compound COc1cc2nccc(Oc(cc3)ccc3NC(C3(CC3)C(Nc(cc3)ccc3F)=O)=O)c2cc1O NHMICDOYSFGBAB-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- VUPGVPMHHNGITC-PLNGDYQASA-N CC(/C=C\C(F)=C)NC(C1(CC1)C(Nc(cc1)ccc1Oc1c(cc(c(OC)c2)O)c2ncc1)=O)=O Chemical compound CC(/C=C\C(F)=C)NC(C1(CC1)C(Nc(cc1)ccc1Oc1c(cc(c(OC)c2)O)c2ncc1)=O)=O VUPGVPMHHNGITC-PLNGDYQASA-N 0.000 description 1
- SXEUPNRRVLHPRM-UHFFFAOYSA-N COc(c(OC)cc1ncc2)cc1c2Oc1ccc(C(C2CC2)NC(C2(CC2)C(O)=O)=O)cc1 Chemical compound COc(c(OC)cc1ncc2)cc1c2Oc1ccc(C(C2CC2)NC(C2(CC2)C(O)=O)=O)cc1 SXEUPNRRVLHPRM-UHFFFAOYSA-N 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
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 true JP2016516074A5 (enExample) | 2017-04-20 |
| JP6389238B2 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 (2) | 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 |
|---|---|---|---|---|
| PL2621481T5 (pl) | 2010-09-27 | 2023-03-13 | Exelixis, Inc. | Podwójne inhibitory MET i VEGF do leczenia opornego na kastrację raka prostaty i osteoblastycznych przerzutów do kości |
| CA2826751C (en) | 2011-02-10 | 2021-05-18 | Exelixis, Inc. | Processes for preparing quinoline compounds and pharmaceutical compositions containing such compounds |
| HK1207587A1 (en) | 2012-05-02 | 2016-02-05 | 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 |
| ES2927651T3 (es) | 2013-04-04 | 2022-11-10 | Exelixis Inc | Forma de dosificación de cabozantinib y uso en el tratamiento del cáncer |
| EP3738952A1 (en) | 2014-02-14 | 2020-11-18 | 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 |
| WO2015142928A1 (en) * | 2014-03-17 | 2015-09-24 | Exelixis, Inc. | Dosing of cabozantinib formulations |
| MA40386A (fr) * | 2014-07-31 | 2016-02-04 | Exelixis Inc | Procédé de préparation de cabozantinib marqué au fluor-18 et d'analogues de celui-ci |
| EA034992B1 (ru) | 2014-08-05 | 2020-04-15 | Экселиксис, Инк. | Комбинации лекарственных средств для лечения множественной миеломы |
| EP3442531A1 (en) | 2016-04-15 | 2019-02-20 | 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 |
| MY210421A (en) | 2018-01-26 | 2025-09-22 | Exelixis Inc | Compounds for the treatment of kinase-dependent disorders |
| 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 |
| EP4658271A1 (en) | 2023-01-31 | 2025-12-10 | Handa Oncology, LLC | Improved cabozantinib compositions and methods of use |
Family Cites Families (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2392565B1 (en) | 2003-09-26 | 2014-03-19 | Exelixis, Inc. | c-Met modulators and methods of use |
| JP5368701B2 (ja) | 2004-07-02 | 2013-12-18 | エクセリクシス、インコーポレイテッド | ｃ−Ｍｅｔモジュレーター及び使用方法 |
| CA2603748A1 (en) | 2005-04-06 | 2006-10-12 | Exelixis, Inc. | C-met modulators and methods of use |
| UY30183A1 (es) | 2006-03-02 | 2007-10-31 | Astrazeneca Ab | Derivados de quinolina |
| JP5311673B2 (ja) | 2006-12-14 | 2013-10-09 | エグゼリクシス， インコーポレイテッド | Ｍｅｋ阻害剤の使用方法 |
| 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 |
| 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 |
| WO2010065838A1 (en) | 2008-12-04 | 2010-06-10 | Exelixis, Inc. | Methods of preparing quinoline derivatives |
| RS52754B2 (sr) | 2009-01-16 | 2022-08-31 | Exelixis Inc | Malat so n-(4- {[6,7-bis(metiloksi)hinolin-4-il]oksi}fenil-n'- (4-fluorofenil) ciklopropan-1,1-dikarboksamid-a, i njeni kristalni oblici za lečenje karcinoma |
| 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 | |
| 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 |
| EP2593091A1 (en) | 2010-07-16 | 2013-05-22 | Exelixis, Inc. | C-met modulator pharmaceutical compositions |
| KR20180056807A (ko) | 2010-07-16 | 2018-05-29 | 엑셀리시스, 인코포레이티드 | C-met 조절제 약제학적 조성물 |
| 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 |
| PL2621481T5 (pl) | 2010-09-27 | 2023-03-13 | Exelixis, Inc. | Podwójne inhibitory MET i VEGF do leczenia opornego na kastrację raka prostaty i osteoblastycznych przerzutów do kości |
| 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 |
| JP2013543011A (ja) | 2010-11-22 | 2013-11-28 | グラクソスミスクライン、インテレクチュアル、プロパティー、ナンバー２、リミテッド | 癌の治療法 |
| WO2012088337A1 (en) * | 2010-12-23 | 2012-06-28 | Prometheus Laboratories Inc. | Drug selection for malignant cancer therapy using antibody-based arrays |
| 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 |
| CA2826751C (en) | 2011-02-10 | 2021-05-18 | Exelixis, Inc. | Processes for preparing quinoline compounds and pharmaceutical compositions containing such compounds |
| US20120252840A1 (en) | 2011-04-04 | 2012-10-04 | Exelixis, Inc. | Method of Treating Cancer |
| JP2014513129A (ja) | 2011-05-02 | 2014-05-29 | エクセリクシス， インク． | 癌および骨癌疼痛の治療方法 |
| 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 |
| EP2758057B1 (en) | 2011-09-22 | 2017-05-31 | Exelixis, Inc. | Method for treating osteoporosis |
| CN104395284A (zh) | 2011-10-20 | 2015-03-04 | 埃克塞里艾克西斯公司 | 制备喹啉衍生物的方法 |
| KR20140088610A (ko) | 2011-11-08 | 2014-07-10 | 엑셀리시스, 인코포레이티드 | 암을 치료하기 위한 met 및 vegf의 이중 저해제 |
| HK1207587A1 (en) | 2012-05-02 | 2016-02-05 | Exelixis, Inc. | A dual met - vegf modulator for treating osteolytic bone metastases |
| WO2014039971A1 (en) | 2012-09-07 | 2014-03-13 | Exelixis, Inc. | Inhibitors of met, vegfr and ret for use in the treatment of lung adenocarcinoma |
| 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 |
| 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 |
| 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 |
| ES2927651T3 (es) | 2013-04-04 | 2022-11-10 | Exelixis Inc | Forma de dosificación de cabozantinib y uso en el tratamiento del cáncer |
| CN108472242A (zh) | 2013-04-04 | 2018-08-31 | 埃克塞里艾克西斯公司 | 治疗癌症的药物组合 |
| EP3738952A1 (en) | 2014-02-14 | 2020-11-18 | 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 |
| WO2015142928A1 (en) | 2014-03-17 | 2015-09-24 | Exelixis, Inc. | Dosing of cabozantinib formulations |
| MA40386A (fr) | 2014-07-31 | 2016-02-04 | Exelixis Inc | Procédé de préparation de cabozantinib marqué au fluor-18 et d'analogues de celui-ci |
-
2014
- 2014-03-17 GE GEAP201413960A patent/GEP20196995B/en unknown
- 2014-03-17 EP EP14721149.4A patent/EP2970126B1/en active Active
- 2014-03-17 CN CN201480021215.XA patent/CN105121412B/zh active Active
- 2014-03-17 WO PCT/US2014/030524 patent/WO2014145715A1/en not_active Ceased
- 2014-03-17 BR BR112015023109-8A patent/BR112015023109A2/en not_active Application Discontinuation
- 2014-03-17 GE GEAP201913960A patent/GEAP201913960A/en unknown
- 2014-03-17 KR KR1020157027712A patent/KR102276348B1/ko active Active
- 2014-03-17 AU AU2014232714A patent/AU2014232714B2/en active Active
- 2014-03-17 MX MX2015012490A patent/MX366003B/es active IP Right Grant
- 2014-03-17 JP JP2016503412A patent/JP6389238B2/ja 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 EA EA201591756A patent/EA033786B1/ru not_active IP Right Cessation
- 2014-03-17 US US14/776,337 patent/US10273211B2/en active Active
- 2014-03-17 NZ NZ712330A patent/NZ712330A/en unknown
- 2014-03-17 UA UAA201510088A patent/UA119321C2/uk unknown
-
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
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