JP2020521732A5 - - Google Patents
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- Publication number
- JP2020521732A5 JP2020521732A5 JP2019562380A JP2019562380A JP2020521732A5 JP 2020521732 A5 JP2020521732 A5 JP 2020521732A5 JP 2019562380 A JP2019562380 A JP 2019562380A JP 2019562380 A JP2019562380 A JP 2019562380A JP 2020521732 A5 JP2020521732 A5 JP 2020521732A5
- Authority
- JP
- Japan
- Prior art keywords
- crystalline solid
- compound
- cancer
- glutarate
- pyruvate
- 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
- 229940125904 compound 1 Drugs 0.000 claims description 60
- 239000007787 solid Substances 0.000 claims description 54
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 29
- LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 claims description 28
- IZGZJJKGQDJABQ-UHFFFAOYSA-N 2-hydroxyethanesulfonic acid;hydrate Chemical compound O.OCCS(O)(=O)=O IZGZJJKGQDJABQ-UHFFFAOYSA-N 0.000 claims description 20
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- -1 6,7-dimethoxyquinoline-4-yl Chemical group 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 206010028980 Neoplasm Diseases 0.000 claims description 11
- 150000004682 monohydrates Chemical class 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 238000001228 spectrum Methods 0.000 claims description 8
- 230000004580 weight loss Effects 0.000 claims description 8
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims description 6
- 238000000113 differential scanning calorimetry Methods 0.000 claims description 6
- 238000004455 differential thermal analysis Methods 0.000 claims description 6
- 238000001179 sorption measurement Methods 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 201000011510 cancer Diseases 0.000 claims description 5
- 238000001757 thermogravimetry curve Methods 0.000 claims description 5
- 206010005949 Bone cancer Diseases 0.000 claims description 4
- 208000018084 Bone neoplasm Diseases 0.000 claims description 4
- 206010060862 Prostate cancer Diseases 0.000 claims description 4
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 229950000886 isetionate Drugs 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 238000002411 thermogravimetry Methods 0.000 claims description 4
- 208000003174 Brain Neoplasms Diseases 0.000 claims description 3
- 208000008839 Kidney Neoplasms Diseases 0.000 claims description 3
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 3
- 206010038389 Renal cancer Diseases 0.000 claims description 3
- 208000024770 Thyroid neoplasm Diseases 0.000 claims description 3
- 201000010982 kidney cancer Diseases 0.000 claims description 3
- 201000007270 liver cancer Diseases 0.000 claims description 3
- 208000014018 liver neoplasm Diseases 0.000 claims description 3
- 201000005202 lung cancer Diseases 0.000 claims description 3
- 208000020816 lung neoplasm Diseases 0.000 claims description 3
- 201000002510 thyroid cancer Diseases 0.000 claims description 3
- 206010005003 Bladder cancer Diseases 0.000 claims description 2
- 206010008342 Cervix carcinoma Diseases 0.000 claims description 2
- 206010009944 Colon cancer Diseases 0.000 claims description 2
- 208000000461 Esophageal Neoplasms Diseases 0.000 claims description 2
- 201000003741 Gastrointestinal carcinoma Diseases 0.000 claims description 2
- 208000017604 Hodgkin disease Diseases 0.000 claims description 2
- 208000010747 Hodgkins lymphoma Diseases 0.000 claims description 2
- 206010025323 Lymphomas Diseases 0.000 claims description 2
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims description 2
- 206010030155 Oesophageal carcinoma Diseases 0.000 claims description 2
- 206010033128 Ovarian cancer Diseases 0.000 claims description 2
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 2
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 2
- 208000005718 Stomach Neoplasms Diseases 0.000 claims description 2
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 2
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims description 2
- 201000010881 cervical cancer Diseases 0.000 claims description 2
- 208000029742 colonic neoplasm Diseases 0.000 claims description 2
- 201000004101 esophageal cancer Diseases 0.000 claims description 2
- 206010017758 gastric cancer Diseases 0.000 claims description 2
- 201000002313 intestinal cancer Diseases 0.000 claims description 2
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 2
- 201000002528 pancreatic cancer Diseases 0.000 claims description 2
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 201000011549 stomach cancer Diseases 0.000 claims description 2
- 201000005112 urinary bladder cancer Diseases 0.000 claims description 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 208000005017 glioblastoma Diseases 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 230000002159 abnormal effect Effects 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 210000001130 astrocyte Anatomy 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 230000002018 overexpression Effects 0.000 description 2
- 208000009018 Medullary thyroid cancer Diseases 0.000 description 1
- 208000006265 Renal cell carcinoma Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 201000011610 giant cell glioblastoma Diseases 0.000 description 1
- 206010073071 hepatocellular carcinoma Diseases 0.000 description 1
- 231100000844 hepatocellular carcinoma Toxicity 0.000 description 1
- 229930182851 human metabolite Natural products 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 208000023356 medullary thyroid gland carcinoma Diseases 0.000 description 1
- 208000002154 non-small cell lung carcinoma Diseases 0.000 description 1
- 210000004248 oligodendroglia Anatomy 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 description 1
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2022127094A JP7437460B2 (ja) | 2017-05-26 | 2022-08-09 | Ｎ－｛４－［（６，７－ジメトキシキノリン－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塩の結晶性固体形態、製造プロセス、及び使用方法 |
| JP2024018527A JP7659097B2 (ja) | 2017-05-26 | 2024-02-09 | Ｎ－｛４－［（６，７－ジメトキシキノリン－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塩の結晶性固体形態、製造プロセス、及び使用方法 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762511714P | 2017-05-26 | 2017-05-26 | |
| US62/511,714 | 2017-05-26 | ||
| PCT/US2018/034784 WO2018218233A1 (en) | 2017-05-26 | 2018-05-26 | Crystalline solid forms of salts of n-{4-[(6,7-dimethoxyquinolin-4-yl) oxy]phenyl}-n'-(4-fluorphenyl) cyclopropane-1,1-dicarboxamide, processes for making, and methods of use |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022127094A Division JP7437460B2 (ja) | 2017-05-26 | 2022-08-09 | Ｎ－｛４－［（６，７－ジメトキシキノリン－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塩の結晶性固体形態、製造プロセス、及び使用方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020521732A JP2020521732A (ja) | 2020-07-27 |
| JP2020521732A5 true JP2020521732A5 (enExample) | 2021-07-26 |
| JP7166292B2 JP7166292B2 (ja) | 2022-11-07 |
Family
ID=62683441
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019562380A Active JP7166292B2 (ja) | 2017-05-26 | 2018-05-26 | Ｎ－｛４－［（６，７－ジメトキシキノリン－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塩の結晶性固体形態、製造プロセス、及び使用方法 |
| JP2022127094A Active JP7437460B2 (ja) | 2017-05-26 | 2022-08-09 | Ｎ－｛４－［（６，７－ジメトキシキノリン－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塩の結晶性固体形態、製造プロセス、及び使用方法 |
| JP2024018527A Active JP7659097B2 (ja) | 2017-05-26 | 2024-02-09 | Ｎ－｛４－［（６，７－ジメトキシキノリン－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塩の結晶性固体形態、製造プロセス、及び使用方法 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022127094A Active JP7437460B2 (ja) | 2017-05-26 | 2022-08-09 | Ｎ－｛４－［（６，７－ジメトキシキノリン－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塩の結晶性固体形態、製造プロセス、及び使用方法 |
| JP2024018527A Active JP7659097B2 (ja) | 2017-05-26 | 2024-02-09 | Ｎ－｛４－［（６，７－ジメトキシキノリン－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塩の結晶性固体形態、製造プロセス、及び使用方法 |
Country Status (20)
| Country | Link |
|---|---|
| US (3) | US11279675B2 (enExample) |
| EP (1) | EP3630726B1 (enExample) |
| JP (3) | JP7166292B2 (enExample) |
| KR (1) | KR102611445B1 (enExample) |
| CN (1) | CN110621662B (enExample) |
| AU (1) | AU2018272088C1 (enExample) |
| CA (1) | CA3060370A1 (enExample) |
| DK (1) | DK3630726T3 (enExample) |
| EA (1) | EA039654B1 (enExample) |
| ES (1) | ES2909390T3 (enExample) |
| HU (1) | HUE058196T2 (enExample) |
| IL (1) | IL270780B2 (enExample) |
| MA (1) | MA48776A (enExample) |
| MX (1) | MX2019012505A (enExample) |
| PL (1) | PL3630726T3 (enExample) |
| PT (1) | PT3630726T (enExample) |
| SG (1) | SG11201909161PA (enExample) |
| UA (1) | UA127760C2 (enExample) |
| WO (1) | WO2018218233A1 (enExample) |
| ZA (1) | ZA201906127B (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| PT3630726T (pt) * | 2017-05-26 | 2022-03-02 | Exelixis Inc | Formas sólidas cristalinas de sais de n-{4-[(6,7-dimetoxiquinolin- 4-il)oxi]fenil}-n¿-(4-fluorfenil)ciclopropano-1,1- dicarboxamida, processos para a preparação e métodos de utilização |
| MA51673B1 (fr) | 2018-01-26 | 2025-10-31 | Exelixis, Inc. | Composés pour le traitement des troubles dépendants de kinases |
| EP3806858A4 (en) | 2018-06-15 | 2022-03-09 | Handa Pharmaceuticals, Inc. | KINA INHIBITOR SALTS AND COMPOSITIONS THEREOF |
| SG11202105949RA (en) | 2018-12-13 | 2021-07-29 | Exelixis Inc | Crystalline forms and salt forms of a kinase inhibitor |
| PH12021553020A1 (en) * | 2019-06-03 | 2023-08-23 | Exelixis Inc | Crystalline salt forms of a kinase inhibitor |
| EP4486725A1 (en) | 2022-03-01 | 2025-01-08 | Synthon B.V. | Cabozantinib salt with l-(+)-tartaric acid and solid forms thereof |
| EP4658271A1 (en) | 2023-01-31 | 2025-12-10 | Handa Oncology, LLC | Improved cabozantinib compositions and methods of use |
| US11814356B1 (en) | 2023-03-29 | 2023-11-14 | Apotex Inc. | Salt of cabozantinib |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005030140A2 (en) * | 2003-09-26 | 2005-04-07 | Exelixis, Inc. | C-met modulators and methods of use |
| DK2387563T4 (da) | 2009-01-16 | 2022-07-18 | Exelixis Inc | Malatsalt af n-(4-{ [ 6, 7-bis(methyloxy)quinolin-4-yl]oxy}phenyl-n'-(4-fluorphenyl)cyclopropan-1,1-dicarboxamid, og krystallinske former deraf til behandling af cancer |
| UA108618C2 (uk) | 2009-08-07 | 2015-05-25 | Застосування c-met-модуляторів в комбінації з темозоломідом та/або променевою терапією для лікування раку | |
| US20120070368A1 (en) | 2010-04-16 | 2012-03-22 | Exelixis, Inc. | Methods of Using C-Met Modulators |
| SG187060A1 (en) | 2010-07-16 | 2013-02-28 | Exelixis Inc | C-met modulator pharmaceutical compositions |
| US20140057943A1 (en) | 2010-09-27 | 2014-02-27 | Exelixix, Inc. | Method of Treating Cancer |
| CN103391773A (zh) | 2010-09-27 | 2013-11-13 | 埃克塞里艾克西斯公司 | 用于治疗去势抵抗性前列腺癌和成骨性骨转移的met和vegf的双重抑制剂 |
| KR20230158644A (ko) * | 2011-02-10 | 2023-11-20 | 엑셀리시스, 인코포레이티드 | 퀴놀린 화합물들의 제조 방법들 및 상기 화합물들을 함유하는 약학 조성물들 |
| US20120252840A1 (en) | 2011-04-04 | 2012-10-04 | Exelixis, Inc. | Method of Treating Cancer |
| WO2012151326A1 (en) | 2011-05-02 | 2012-11-08 | Exelixis, Inc. | Method of treating cancer and bone cancer pain |
| CA2848512A1 (en) | 2011-09-22 | 2013-03-28 | Exelixis, Inc. | Method for treating osteoporosis |
| WO2013066296A1 (en) | 2011-10-31 | 2013-05-10 | Hewlett-Packard Development Company, L.P. | Method of fabricating a color filter array using a multilevel structure |
| EA201490944A1 (ru) | 2011-11-08 | 2014-10-30 | Экселиксис, Инк. | Двойной ингибитор met и vegf для лечения рака |
| WO2013070903A1 (en) | 2011-11-08 | 2013-05-16 | Exelixis, Inc. | Method of quantifying cancer treatment |
| 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 |
| 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 |
| WO2015177758A1 (en) * | 2014-05-23 | 2015-11-26 | Mylan Laboratories Ltd | Novel polymorphs of cabozantinib (s)-malate and cabozantinib free base |
| CN104961680B (zh) | 2014-11-07 | 2017-09-12 | 苏州晶云药物科技有限公司 | N‑(4‑{[6,7‑双(甲基氧基)喹啉‑4‑基]氧基}苯基)‑n’‑(4‑氟苯基)环丙烷‑1,1‑二甲酰胺的盐酸盐及其多晶型 |
| CN104961681B (zh) | 2014-11-13 | 2017-06-13 | 苏州晶云药物科技有限公司 | 卡博替尼的粘酸盐及其晶型 |
| US10053427B2 (en) | 2015-03-25 | 2018-08-21 | Sandoz Ag | Crystalline forms of cabozantinib phosphate and cabozantinib hydrochloride |
| EP3274333B1 (en) * | 2015-03-25 | 2019-04-24 | Sandoz AG | Cabozantinib salts and their use as anti-cancer agents |
| WO2018049329A1 (en) * | 2016-09-12 | 2018-03-15 | Zhuhai Beihai Biotech Co., Ltd. | Formulations of cabozantinib |
| WO2018104954A1 (en) * | 2016-12-07 | 2018-06-14 | Msn Laboratories Private Limited, R&D Center | Process for the preparation of n-(4-(6,7-dimethoxyquinolin-4-yloxy) phenyl)-n'-(4-fluorophenyl)cyclopropane-1, 1-dicarboxamide, (2s)-hydroxybutanedioate and its polymorphs thereof |
| PT3630726T (pt) | 2017-05-26 | 2022-03-02 | Exelixis Inc | Formas sólidas cristalinas de sais de n-{4-[(6,7-dimetoxiquinolin- 4-il)oxi]fenil}-n¿-(4-fluorfenil)ciclopropano-1,1- dicarboxamida, processos para a preparação e métodos de utilização |
-
2018
- 2018-05-26 PT PT187325485T patent/PT3630726T/pt unknown
- 2018-05-26 SG SG11201909161P patent/SG11201909161PA/en unknown
- 2018-05-26 WO PCT/US2018/034784 patent/WO2018218233A1/en not_active Ceased
- 2018-05-26 MA MA048776A patent/MA48776A/fr unknown
- 2018-05-26 KR KR1020197031409A patent/KR102611445B1/ko active Active
- 2018-05-26 EP EP18732548.5A patent/EP3630726B1/en active Active
- 2018-05-26 JP JP2019562380A patent/JP7166292B2/ja active Active
- 2018-05-26 CN CN201880027861.5A patent/CN110621662B/zh active Active
- 2018-05-26 ES ES18732548T patent/ES2909390T3/es active Active
- 2018-05-26 AU AU2018272088A patent/AU2018272088C1/en active Active
- 2018-05-26 EA EA201992803A patent/EA039654B1/ru unknown
- 2018-05-26 UA UAA201912198A patent/UA127760C2/uk unknown
- 2018-05-26 US US16/617,352 patent/US11279675B2/en active Active
- 2018-05-26 HU HUE18732548A patent/HUE058196T2/hu unknown
- 2018-05-26 MX MX2019012505A patent/MX2019012505A/es unknown
- 2018-05-26 IL IL270780A patent/IL270780B2/en unknown
- 2018-05-26 DK DK18732548.5T patent/DK3630726T3/da active
- 2018-05-26 CA CA3060370A patent/CA3060370A1/en active Pending
- 2018-05-26 PL PL18732548T patent/PL3630726T3/pl unknown
-
2019
- 2019-09-17 ZA ZA2019/06127A patent/ZA201906127B/en unknown
-
2022
- 2022-02-09 US US17/668,098 patent/US11731941B2/en active Active
- 2022-08-09 JP JP2022127094A patent/JP7437460B2/ja active Active
-
2023
- 2023-06-29 US US18/344,267 patent/US12227481B2/en active Active
-
2024
- 2024-02-09 JP JP2024018527A patent/JP7659097B2/ja active Active
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