JP2020535168A5 - - Google Patents
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- JP2020535168A5 JP2020535168A5 JP2020517516A JP2020517516A JP2020535168A5 JP 2020535168 A5 JP2020535168 A5 JP 2020535168A5 JP 2020517516 A JP2020517516 A JP 2020517516A JP 2020517516 A JP2020517516 A JP 2020517516A JP 2020535168 A5 JP2020535168 A5 JP 2020535168A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- salt
- production method
- cancer
- salt according
- 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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- 150000003839 salts Chemical class 0.000 claims description 80
- -1 1-isobutyryl piperidine-4-yl Chemical group 0.000 claims description 64
- 238000004519 manufacturing process Methods 0.000 claims description 58
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 36
- 239000002904 solvent Substances 0.000 claims description 34
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 32
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 30
- 239000000243 solution Substances 0.000 claims description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 25
- 239000002002 slurry Substances 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 14
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 10
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 10
- 239000011976 maleic acid Substances 0.000 claims description 10
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 10
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 10
- 206010028980 Neoplasm Diseases 0.000 claims description 8
- 238000001938 differential scanning calorimetry curve Methods 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 8
- 201000011510 cancer Diseases 0.000 claims description 6
- WVPZJYCGPGSZHW-UHFFFAOYSA-N 2,4-dioxo-3-phenyl-1-propan-2-ylpyrimidine-5-carboxamide Chemical group C(C)(C)N1C(N(C(C(=C1)C(=O)N)=O)C1=CC=CC=C1)=O WVPZJYCGPGSZHW-UHFFFAOYSA-N 0.000 claims description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- 206010006187 Breast cancer Diseases 0.000 claims description 4
- 208000026310 Breast neoplasm Diseases 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 206010009944 Colon cancer Diseases 0.000 claims description 4
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 4
- 206010025323 Lymphomas Diseases 0.000 claims description 4
- 208000034578 Multiple myelomas Diseases 0.000 claims description 4
- 108091000080 Phosphotransferase Proteins 0.000 claims description 4
- 206010035226 Plasma cell myeloma Diseases 0.000 claims description 4
- 206010060862 Prostate cancer Diseases 0.000 claims description 4
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 4
- 208000005718 Stomach Neoplasms Diseases 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 239000000706 filtrate Substances 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 206010017758 gastric cancer Diseases 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 201000005202 lung cancer Diseases 0.000 claims description 4
- 208000020816 lung neoplasm Diseases 0.000 claims description 4
- 201000001441 melanoma Diseases 0.000 claims description 4
- 102000020233 phosphotransferase Human genes 0.000 claims description 4
- 201000011549 stomach cancer Diseases 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 238000001757 thermogravimetry curve Methods 0.000 claims description 4
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 2
- 208000009746 Adult T-Cell Leukemia-Lymphoma Diseases 0.000 claims description 2
- 208000016683 Adult T-cell leukemia/lymphoma Diseases 0.000 claims description 2
- 208000003950 B-cell lymphoma Diseases 0.000 claims description 2
- 206010005003 Bladder cancer Diseases 0.000 claims description 2
- 206010008342 Cervix carcinoma Diseases 0.000 claims description 2
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 2
- 206010014733 Endometrial cancer Diseases 0.000 claims description 2
- 206010014759 Endometrial neoplasm Diseases 0.000 claims description 2
- 208000000461 Esophageal Neoplasms Diseases 0.000 claims description 2
- 208000017604 Hodgkin disease Diseases 0.000 claims description 2
- 208000021519 Hodgkin lymphoma Diseases 0.000 claims description 2
- 208000010747 Hodgkins lymphoma Diseases 0.000 claims description 2
- 208000008839 Kidney Neoplasms Diseases 0.000 claims description 2
- 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims description 2
- 206010052178 Lymphocytic lymphoma Diseases 0.000 claims description 2
- 208000033776 Myeloid Acute Leukemia 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
- 206010038389 Renal cancer Diseases 0.000 claims description 2
- 208000006265 Renal cell carcinoma Diseases 0.000 claims description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 2
- 208000000453 Skin Neoplasms Diseases 0.000 claims description 2
- 208000024770 Thyroid neoplasm 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
- 208000033559 Waldenström macroglobulinemia Diseases 0.000 claims description 2
- 201000006966 adult T-cell leukemia Diseases 0.000 claims description 2
- 201000010881 cervical cancer Diseases 0.000 claims description 2
- 230000001684 chronic effect Effects 0.000 claims description 2
- 208000029742 colonic neoplasm Diseases 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 201000004101 esophageal cancer Diseases 0.000 claims description 2
- 208000005017 glioblastoma Diseases 0.000 claims description 2
- 201000010536 head and neck cancer Diseases 0.000 claims description 2
- 208000014829 head and neck neoplasm Diseases 0.000 claims description 2
- 206010073071 hepatocellular carcinoma Diseases 0.000 claims description 2
- 231100000844 hepatocellular carcinoma Toxicity 0.000 claims description 2
- 201000010982 kidney cancer Diseases 0.000 claims description 2
- 208000032839 leukemia Diseases 0.000 claims description 2
- 201000007270 liver cancer Diseases 0.000 claims description 2
- 208000014018 liver neoplasm Diseases 0.000 claims description 2
- 201000000564 macroglobulinemia 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
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 201000009410 rhabdomyosarcoma Diseases 0.000 claims description 2
- 239000000741 silica gel Substances 0.000 claims description 2
- 229910002027 silica gel Inorganic materials 0.000 claims description 2
- 201000000849 skin cancer Diseases 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 201000002510 thyroid cancer Diseases 0.000 claims description 2
- 201000005112 urinary bladder cancer Diseases 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims 5
- 238000001816 cooling Methods 0.000 claims 1
- 210000002768 hair cell Anatomy 0.000 claims 1
- 230000001376 precipitating effect Effects 0.000 claims 1
- 208000015347 renal cell adenocarcinoma Diseases 0.000 claims 1
- 102000001253 Protein Kinase Human genes 0.000 description 2
- 108060006633 protein kinase Proteins 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2024014546A JP7639195B2 (ja) | 2017-09-27 | 2024-02-02 | Ｔａｍ阻害剤として有用なピロロトリアジン誘導体の塩 |
| JP2025025024A JP2025093936A (ja) | 2017-09-27 | 2025-02-19 | Ｔａｍ阻害剤として有用なピロロトリアジン誘導体の塩 |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762564070P | 2017-09-27 | 2017-09-27 | |
| US62/564,070 | 2017-09-27 | ||
| US201862714196P | 2018-08-03 | 2018-08-03 | |
| US62/714,196 | 2018-08-03 | ||
| PCT/US2018/052925 WO2019067594A1 (en) | 2017-09-27 | 2018-09-26 | Salts of pyrrolotriazine derivatives useful as tam inhibitors |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2024014546A Division JP7639195B2 (ja) | 2017-09-27 | 2024-02-02 | Ｔａｍ阻害剤として有用なピロロトリアジン誘導体の塩 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020535168A JP2020535168A (ja) | 2020-12-03 |
| JP2020535168A5 true JP2020535168A5 (https=) | 2021-10-28 |
| JP7504791B2 JP7504791B2 (ja) | 2024-06-24 |
Family
ID=63794769
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020517516A Active JP7504791B2 (ja) | 2017-09-27 | 2018-09-26 | Ｔａｍ阻害剤として有用なピロロトリアジン誘導体の塩 |
| JP2024014546A Active JP7639195B2 (ja) | 2017-09-27 | 2024-02-02 | Ｔａｍ阻害剤として有用なピロロトリアジン誘導体の塩 |
| JP2025025024A Pending JP2025093936A (ja) | 2017-09-27 | 2025-02-19 | Ｔａｍ阻害剤として有用なピロロトリアジン誘導体の塩 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2024014546A Active JP7639195B2 (ja) | 2017-09-27 | 2024-02-02 | Ｔａｍ阻害剤として有用なピロロトリアジン誘導体の塩 |
| JP2025025024A Pending JP2025093936A (ja) | 2017-09-27 | 2025-02-19 | Ｔａｍ阻害剤として有用なピロロトリアジン誘導体の塩 |
Country Status (34)
| Country | Link |
|---|---|
| US (4) | US10633387B2 (https=) |
| EP (2) | EP3687996B1 (https=) |
| JP (3) | JP7504791B2 (https=) |
| KR (1) | KR102739325B1 (https=) |
| CN (2) | CN111386273B (https=) |
| AU (2) | AU2018342471B2 (https=) |
| CA (1) | CA3077308A1 (https=) |
| CL (2) | CL2020000791A1 (https=) |
| CO (1) | CO2020005009A2 (https=) |
| CR (1) | CR20200179A (https=) |
| CY (1) | CY1124952T1 (https=) |
| DK (1) | DK3687996T3 (https=) |
| EC (1) | ECSP20021655A (https=) |
| ES (1) | ES2904458T3 (https=) |
| GE (2) | GEAP202215322A (https=) |
| HU (1) | HUE057190T2 (https=) |
| IL (1) | IL273579B2 (https=) |
| JO (1) | JOP20200081B1 (https=) |
| LT (1) | LT3687996T (https=) |
| MA (1) | MA50655B1 (https=) |
| MD (1) | MD3687996T2 (https=) |
| MX (1) | MX2020003375A (https=) |
| MY (1) | MY208007A (https=) |
| PE (1) | PE20210002A1 (https=) |
| PH (1) | PH12020550143A1 (https=) |
| PL (1) | PL3687996T3 (https=) |
| PT (1) | PT3687996T (https=) |
| RS (1) | RS62872B1 (https=) |
| SA (1) | SA520411638B1 (https=) |
| SG (1) | SG11202002821UA (https=) |
| SI (1) | SI3687996T1 (https=) |
| SM (1) | SMT202200011T1 (https=) |
| TW (1) | TWI821200B (https=) |
| WO (1) | WO2019067594A1 (https=) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10053465B2 (en) | 2015-08-26 | 2018-08-21 | Incyte Corporation | Pyrrolopyrimidine derivatives as TAM inhibitors |
| SMT202000534T1 (it) | 2015-12-09 | 2020-11-10 | Cadent Therapeutics Inc | Modulatori eteroaromatici del recettore nmda e loro usi |
| MD3436461T2 (ro) | 2016-03-28 | 2024-05-31 | Incyte Corp | Compuși pirolotriazină ca inhibitori TAM |
| ES2975336T3 (es) | 2016-12-22 | 2024-07-04 | Novartis Ag | Moduladores del receptor NMDA y usos de los mismos |
| SI3687996T1 (sl) * | 2017-09-27 | 2022-04-29 | Incyte Corporation | Soli pirolotriazinskih derivatov, ki so uporabne kot zaviralci TAM |
| MD3813800T2 (ro) | 2018-06-29 | 2025-10-31 | Incyte Corp | Formulări de inhibitor al AXL/MER |
| BR112021001967A2 (pt) | 2018-08-03 | 2021-04-27 | Cadent Therapeutics, Inc. | moduladores de receptor nmda heteroaromáticos e usos dos mesmos |
| CR20250050A (es) | 2018-09-05 | 2025-03-19 | Incyte Corp | Formas cristalinas de un inhibidor de fosfoinositida 3–quinasa (pi3k) (divisional 2021-0165) |
| EP4114401A1 (en) | 2020-03-06 | 2023-01-11 | Incyte Corporation | Combination therapy comprising axl/mer and pd-1/pd-l1 inhibitors |
| WO2022007921A1 (zh) * | 2020-07-10 | 2022-01-13 | 北京范恩柯尔生物科技有限公司 | 三嗪类化合物及其组合物和用途 |
| CN115028648B (zh) * | 2021-03-03 | 2024-08-30 | 武汉誉祥医药科技有限公司 | 三并环化合物及其药物组合物和应用 |
| US20240317692A1 (en) * | 2021-07-13 | 2024-09-26 | Nippon Soda Co., Ltd. | Method for producing uracil compound |
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