JPWO2017206924A5 - - Google Patents
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- Publication number
- JPWO2017206924A5 JPWO2017206924A5 JP2018563619A JP2018563619A JPWO2017206924A5 JP WO2017206924 A5 JPWO2017206924 A5 JP WO2017206924A5 JP 2018563619 A JP2018563619 A JP 2018563619A JP 2018563619 A JP2018563619 A JP 2018563619A JP WO2017206924 A5 JPWO2017206924 A5 JP WO2017206924A5
- Authority
- JP
- Japan
- Prior art keywords
- crystals
- formula
- compound
- crystal
- hydrate
- 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
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- 239000013078 crystal Substances 0.000 claims description 210
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 134
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 126
- 150000001875 compounds Chemical class 0.000 claims description 114
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 69
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 68
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 60
- 239000002904 solvent Substances 0.000 claims description 51
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 44
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 42
- 239000008194 pharmaceutical composition Substances 0.000 claims description 42
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 41
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 37
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 34
- 239000000706 filtrate Substances 0.000 claims description 33
- 239000012453 solvate Substances 0.000 claims description 33
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 31
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 30
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 25
- 238000001914 filtration Methods 0.000 claims description 23
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 22
- 201000010099 disease Diseases 0.000 claims description 22
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 22
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 claims description 21
- 238000002360 preparation method Methods 0.000 claims description 21
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 20
- 208000035475 disorder Diseases 0.000 claims description 20
- 239000000725 suspension Substances 0.000 claims description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 18
- 238000003756 stirring Methods 0.000 claims description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 16
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 16
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 12
- 239000007787 solid Substances 0.000 claims description 11
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 10
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims description 10
- 238000001035 drying Methods 0.000 claims description 9
- 102100033793 ALK tyrosine kinase receptor Human genes 0.000 claims description 8
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 8
- 229940011051 isopropyl acetate Drugs 0.000 claims description 8
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 7
- 102000037865 fusion proteins Human genes 0.000 claims description 7
- 108020001507 fusion proteins Proteins 0.000 claims description 7
- 239000002671 adjuvant Substances 0.000 claims description 6
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 6
- 150000004677 hydrates Chemical class 0.000 claims description 6
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims description 5
- 239000001768 carboxy methyl cellulose Substances 0.000 claims description 5
- 235000010948 carboxy methyl cellulose Nutrition 0.000 claims description 5
- 239000008112 carboxymethyl-cellulose Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 102100035108 High affinity nerve growth factor receptor Human genes 0.000 claims description 4
- 101000779641 Homo sapiens ALK tyrosine kinase receptor Proteins 0.000 claims description 4
- 101000596894 Homo sapiens High affinity nerve growth factor receptor Proteins 0.000 claims description 4
- 101000686031 Homo sapiens Proto-oncogene tyrosine-protein kinase ROS Proteins 0.000 claims description 4
- 102100023347 Proto-oncogene tyrosine-protein kinase ROS Human genes 0.000 claims description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 150000004683 dihydrates Chemical class 0.000 claims description 3
- 102100035080 BDNF/NT-3 growth factors receptor Human genes 0.000 claims description 2
- 108010055196 EphA2 Receptor Proteins 0.000 claims description 2
- 102100030340 Ephrin type-A receptor 2 Human genes 0.000 claims description 2
- 239000001856 Ethyl cellulose Substances 0.000 claims description 2
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 claims description 2
- 101000596896 Homo sapiens BDNF/NT-3 growth factors receptor Proteins 0.000 claims description 2
- 101000916644 Homo sapiens Macrophage colony-stimulating factor 1 receptor Proteins 0.000 claims description 2
- 102100028198 Macrophage colony-stimulating factor 1 receptor Human genes 0.000 claims description 2
- 102100029166 NT-3 growth factor receptor Human genes 0.000 claims description 2
- 101150117329 NTRK3 gene Proteins 0.000 claims description 2
- 229920002518 Polyallylamine hydrochloride Polymers 0.000 claims description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 2
- 229920003081 Povidone K 30 Polymers 0.000 claims description 2
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 claims description 2
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 claims description 2
- 235000019325 ethyl cellulose Nutrition 0.000 claims description 2
- 229920001249 ethyl cellulose Polymers 0.000 claims description 2
- 230000001404 mediated effect Effects 0.000 claims description 2
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 claims description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 150000004684 trihydrates Chemical class 0.000 claims description 2
- 208000011117 substance-related disease Diseases 0.000 claims 4
- 230000001575 pathological effect Effects 0.000 claims 3
- 208000007848 Alcoholism Diseases 0.000 claims 2
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims 2
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims 2
- 238000001704 evaporation Methods 0.000 claims 2
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims 2
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims 2
- 201000001441 melanoma Diseases 0.000 claims 2
- 208000020016 psychiatric disease Diseases 0.000 claims 2
- 101710168331 ALK tyrosine kinase receptor Proteins 0.000 claims 1
- 206010005949 Bone cancer Diseases 0.000 claims 1
- 208000018084 Bone neoplasm Diseases 0.000 claims 1
- 208000003174 Brain Neoplasms Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 229920002785 Croscarmellose sodium Polymers 0.000 claims 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims 1
- 206010013654 Drug abuse Diseases 0.000 claims 1
- 208000032612 Glial tumor Diseases 0.000 claims 1
- 206010018338 Glioma Diseases 0.000 claims 1
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 1
- 239000002146 L01XE16 - Crizotinib Substances 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 206010025323 Lymphomas Diseases 0.000 claims 1
- 229930195725 Mannitol Natural products 0.000 claims 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 claims 1
- 101100262697 Mus musculus Axl gene Proteins 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- 206010029260 Neuroblastoma Diseases 0.000 claims 1
- 208000025966 Neurological disease Diseases 0.000 claims 1
- 241000208125 Nicotiana Species 0.000 claims 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 206010038389 Renal cancer Diseases 0.000 claims 1
- 208000006265 Renal cell carcinoma Diseases 0.000 claims 1
- 208000000453 Skin Neoplasms Diseases 0.000 claims 1
- 208000000102 Squamous Cell Carcinoma of Head and Neck Diseases 0.000 claims 1
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 claims 1
- 206010001584 alcohol abuse Diseases 0.000 claims 1
- 208000025746 alcohol use disease Diseases 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 239000001913 cellulose Substances 0.000 claims 1
- 229920002678 cellulose Polymers 0.000 claims 1
- 235000010980 cellulose Nutrition 0.000 claims 1
- 229960003920 cocaine Drugs 0.000 claims 1
- 208000029742 colonic neoplasm Diseases 0.000 claims 1
- KTEIFNKAUNYNJU-GFCCVEGCSA-N crizotinib Chemical compound O([C@H](C)C=1C(=C(F)C=CC=1Cl)Cl)C(C(=NC=1)N)=CC=1C(=C1)C=NN1C1CCNCC1 KTEIFNKAUNYNJU-GFCCVEGCSA-N 0.000 claims 1
- 229960005061 crizotinib Drugs 0.000 claims 1
- 229960001681 croscarmellose sodium Drugs 0.000 claims 1
- 229960000913 crospovidone Drugs 0.000 claims 1
- 235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 206010013663 drug dependence Diseases 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 201000000459 head and neck squamous cell carcinoma Diseases 0.000 claims 1
- 206010073071 hepatocellular carcinoma Diseases 0.000 claims 1
- 231100000844 hepatocellular carcinoma Toxicity 0.000 claims 1
- 229940071676 hydroxypropylcellulose Drugs 0.000 claims 1
- 201000010982 kidney cancer Diseases 0.000 claims 1
- 201000007270 liver cancer Diseases 0.000 claims 1
- 208000014018 liver neoplasm Diseases 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 208000020816 lung neoplasm Diseases 0.000 claims 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 1
- 239000000594 mannitol Substances 0.000 claims 1
- 235000010355 mannitol Nutrition 0.000 claims 1
- 229960001855 mannitol Drugs 0.000 claims 1
- 239000008108 microcrystalline cellulose Substances 0.000 claims 1
- 229940016286 microcrystalline cellulose Drugs 0.000 claims 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 claims 1
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims 1
- 201000002528 pancreatic cancer Diseases 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
- 201000010279 papillary renal cell carcinoma Diseases 0.000 claims 1
- 229920000523 polyvinylpolypyrrolidone Polymers 0.000 claims 1
- 235000013809 polyvinylpolypyrrolidone Nutrition 0.000 claims 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims 1
- 229940069328 povidone Drugs 0.000 claims 1
- 230000002062 proliferating effect Effects 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 201000000849 skin cancer Diseases 0.000 claims 1
- 239000008109 sodium starch glycolate Substances 0.000 claims 1
- 229920003109 sodium starch glycolate Polymers 0.000 claims 1
- 229940079832 sodium starch glycolate Drugs 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- 201000009032 substance abuse Diseases 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 1
- 238000002474 experimental method Methods 0.000 description 14
- 241000700159 Rattus Species 0.000 description 4
- 239000012458 free base Substances 0.000 description 4
- 238000002604 ultrasonography Methods 0.000 description 4
- 102000001253 Protein Kinase Human genes 0.000 description 3
- 108060006633 protein kinase Proteins 0.000 description 3
- -1 2,6-dichloro-3-fluorophenyl Chemical group 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 210000004731 jugular vein Anatomy 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002525 ultrasonication Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNPCT/CN2016/084300 | 2016-06-01 | ||
| CNPCT/CN2016/084300 | 2016-06-01 | ||
| PCT/CN2017/086760 WO2017206924A1 (zh) | 2016-06-01 | 2017-06-01 | 抑制蛋白激酶活性化合物的晶型及其应用 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| JP2019518026A JP2019518026A (ja) | 2019-06-27 |
| JPWO2017206924A5 true JPWO2017206924A5 (https=) | 2022-03-15 |
| JP2019518026A5 JP2019518026A5 (https=) | 2022-03-15 |
| JP7054528B2 JP7054528B2 (ja) | 2022-04-14 |
Family
ID=60477983
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018563619A Active JP7054528B2 (ja) | 2016-06-01 | 2017-06-01 | プロテインキナーゼ活性を抑制する化合物の結晶形態、及びその適用 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US10899744B2 (https=) |
| EP (1) | EP3470410B1 (https=) |
| JP (1) | JP7054528B2 (https=) |
| KR (1) | KR102466958B1 (https=) |
| CN (1) | CN109195964B (https=) |
| AU (1) | AU2017274110B2 (https=) |
| CA (1) | CA3026142C (https=) |
| EA (1) | EA201892687A1 (https=) |
| ES (1) | ES2981015T3 (https=) |
| IL (1) | IL263356B (https=) |
| MY (1) | MY188379A (https=) |
| PH (1) | PH12018502529A1 (https=) |
| PL (1) | PL3470410T3 (https=) |
| RU (1) | RU2744264C2 (https=) |
| SG (1) | SG11201810800VA (https=) |
| TW (1) | TWI646094B (https=) |
| WO (1) | WO2017206924A1 (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL279579B2 (en) | 2018-06-21 | 2023-02-01 | Betta Pharmaceuticals Co Ltd | Crystalline form of a compound to inhibit the activity of cdk4/6 and its use |
| EP4188922A1 (en) | 2020-08-03 | 2023-06-07 | Teva Pharmaceuticals International GmbH | Solid state forms of ensartinib and ensartinib salts |
| EP4385510A4 (en) * | 2021-08-10 | 2025-08-20 | Betta Pharmaceuticals Co Ltd | USE OF ENSARTINIB OR A CORRESPONDING SALT IN THE TREATMENT OF A DISEASE CARRYING A MET EXON 14 SKIPPING MUTATION |
| KR102851417B1 (ko) * | 2022-08-16 | 2025-08-28 | 제이투에이치바이오텍 (주) | 피리미딘-4-카복사마이드 화합물의 결정형 및 이를 포함하는 경구용 약학 제제 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL358271A1 (pl) * | 2000-03-06 | 2004-08-09 | Warner-Lambert Company | 5-alkilopirydo[2,3-D]pirymidyny jako inhibitory kinazy tyrozyny |
| CA2517256C (en) * | 2003-02-26 | 2013-04-30 | Sugen, Inc. | Aminoheteroaryl compounds as protein kinase inhibitors |
| US8414489B2 (en) | 2003-11-13 | 2013-04-09 | Medtronic Minimed, Inc. | Fabrication of multi-sensor arrays |
| ME01309B (me) * | 2004-08-26 | 2013-12-20 | Pfizer | Pirazolom supstituirani heteroarilni spojevi kao inhibitori proteinskih kinaza |
| BRPI0514687A (pt) | 2004-08-26 | 2008-06-17 | Pfizer | compostos amino heteroarila como inibidores de proteìna tirosina cinase |
| KR101146852B1 (ko) * | 2005-12-05 | 2012-05-16 | 화이자 프로덕츠 인크. | Ｃ?ｍｅｔ／ｈｇｆｒ 억제제의 다형체 |
| CN101652068A (zh) * | 2007-01-19 | 2010-02-17 | 艾科睿制药公司 | 激酶抑制物化合物 |
| ES2670665T3 (es) * | 2008-06-19 | 2018-05-31 | Xcovery Holding Company Llc | Compuestos de piridazina carboxamida sustituidos como compuestos inhibidores de quinasa |
| EA024809B1 (ru) * | 2010-10-08 | 2016-10-31 | Икскавери Холдинг Кампани, Ллс | Замещенные соединения пиридазинкарбоксамида |
| WO2012048258A2 (en) * | 2010-10-08 | 2012-04-12 | Xcovery Holding Company, Llc | Substituted pyridazine carboxamide compounds as kinase inhibitor compounds |
-
2017
- 2017-05-31 TW TW106117900A patent/TWI646094B/zh active
- 2017-06-01 WO PCT/CN2017/086760 patent/WO2017206924A1/zh not_active Ceased
- 2017-06-01 PL PL17805869.9T patent/PL3470410T3/pl unknown
- 2017-06-01 ES ES17805869T patent/ES2981015T3/es active Active
- 2017-06-01 KR KR1020187038142A patent/KR102466958B1/ko active Active
- 2017-06-01 IL IL263356A patent/IL263356B/en unknown
- 2017-06-01 EP EP17805869.9A patent/EP3470410B1/en active Active
- 2017-06-01 SG SG11201810800VA patent/SG11201810800VA/en unknown
- 2017-06-01 CN CN201780006852.3A patent/CN109195964B/zh active Active
- 2017-06-01 JP JP2018563619A patent/JP7054528B2/ja active Active
- 2017-06-01 MY MYPI2018002245A patent/MY188379A/en unknown
- 2017-06-01 CA CA3026142A patent/CA3026142C/en active Active
- 2017-06-01 US US16/306,104 patent/US10899744B2/en active Active
- 2017-06-01 RU RU2018145183A patent/RU2744264C2/ru active
- 2017-06-01 EA EA201892687A patent/EA201892687A1/ru unknown
- 2017-06-01 AU AU2017274110A patent/AU2017274110B2/en active Active
-
2018
- 2018-11-29 PH PH12018502529A patent/PH12018502529A1/en unknown
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