JP2017519818A5 - - Google Patents
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- Publication number
- JP2017519818A5 JP2017519818A5 JP2017516254A JP2017516254A JP2017519818A5 JP 2017519818 A5 JP2017519818 A5 JP 2017519818A5 JP 2017516254 A JP2017516254 A JP 2017516254A JP 2017516254 A JP2017516254 A JP 2017516254A JP 2017519818 A5 JP2017519818 A5 JP 2017519818A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- benzo
- imidazol
- butyl
- tert
- 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
- -1 5- (tert-butyl) isoxazol-3-yl Chemical group 0.000 claims description 99
- 238000000034 method Methods 0.000 claims description 47
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 29
- 150000001875 compounds Chemical class 0.000 claims description 27
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims description 26
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 20
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 17
- 102100033177 Vascular endothelial growth factor receptor 2 Human genes 0.000 claims description 16
- 102100035108 High affinity nerve growth factor receptor Human genes 0.000 claims description 12
- 101000579425 Homo sapiens Proto-oncogene tyrosine-protein kinase receptor Ret Proteins 0.000 claims description 12
- 102100028286 Proto-oncogene tyrosine-protein kinase receptor Ret Human genes 0.000 claims description 12
- 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 claims description 11
- 101000851007 Homo sapiens Vascular endothelial growth factor receptor 2 Proteins 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 9
- 206010028980 Neoplasm Diseases 0.000 claims description 9
- 201000011510 cancer Diseases 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 8
- 230000002401 inhibitory effect Effects 0.000 claims description 7
- 208000024770 Thyroid neoplasm Diseases 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 201000002510 thyroid cancer Diseases 0.000 claims description 6
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims description 4
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims description 4
- 108091008605 VEGF receptors Proteins 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 230000026731 phosphorylation Effects 0.000 claims description 4
- 238000006366 phosphorylation reaction Methods 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 102100035080 BDNF/NT-3 growth factors receptor Human genes 0.000 claims description 2
- 101710101214 BDNF/NT-3 growth factors receptor Proteins 0.000 claims description 2
- 206010006187 Breast cancer Diseases 0.000 claims description 2
- 208000026310 Breast neoplasm Diseases 0.000 claims description 2
- 206010058019 Cancer Pain Diseases 0.000 claims description 2
- 101710091869 High affinity nerve growth factor receptor Proteins 0.000 claims description 2
- 101000692455 Homo sapiens Platelet-derived growth factor receptor beta Proteins 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 2
- 102100029166 NT-3 growth factor receptor Human genes 0.000 claims description 2
- 101710145851 NT-3 growth factor receptor Proteins 0.000 claims description 2
- 108091000080 Phosphotransferase Proteins 0.000 claims description 2
- 102100026547 Platelet-derived growth factor receptor beta Human genes 0.000 claims description 2
- 102000016971 Proto-Oncogene Proteins c-kit Human genes 0.000 claims description 2
- 108010014608 Proto-Oncogene Proteins c-kit Proteins 0.000 claims description 2
- 101150077555 Ret gene Proteins 0.000 claims description 2
- 108010053099 Vascular Endothelial Growth Factor Receptor-2 Proteins 0.000 claims description 2
- 239000002246 antineoplastic agent Substances 0.000 claims description 2
- 229940041181 antineoplastic drug Drugs 0.000 claims description 2
- 235000019000 fluorine Nutrition 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 201000005202 lung cancer Diseases 0.000 claims description 2
- 208000020816 lung neoplasm Diseases 0.000 claims description 2
- 102000020233 phosphotransferase Human genes 0.000 claims description 2
- 229940002612 prodrug Drugs 0.000 claims description 2
- 239000000651 prodrug Substances 0.000 claims description 2
- 239000012453 solvate Substances 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 8
- 210000001685 thyroid gland Anatomy 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 39
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 39
- 229910052744 lithium Inorganic materials 0.000 description 39
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 35
- 229940022663 acetate Drugs 0.000 description 35
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 26
- 229940121358 tyrosine kinase inhibitor Drugs 0.000 description 16
- 239000005483 tyrosine kinase inhibitor Substances 0.000 description 16
- 150000004917 tyrosine kinase inhibitor derivatives Chemical class 0.000 description 15
- 150000002148 esters Chemical class 0.000 description 6
- 239000002243 precursor Substances 0.000 description 6
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 125000003106 haloaryl group Chemical group 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- 150000001448 anilines Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 2
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- 125000003226 pyrazolyl group Chemical group 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- HOFXFKYTWSEYDP-UHFFFAOYSA-N 4-(4-bromo-2-nitroanilino)phenol Chemical compound C1=CC(O)=CC=C1NC1=CC=C(Br)C=C1[N+]([O-])=O HOFXFKYTWSEYDP-UHFFFAOYSA-N 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- YDTMRMVSMBHZRP-UHFFFAOYSA-N 6-(1-methylpyrazol-4-yl)-1h-benzimidazole Chemical compound C1=NN(C)C=C1C1=CC=C(N=CN2)C2=C1 YDTMRMVSMBHZRP-UHFFFAOYSA-N 0.000 description 1
- DVMILACIDBEACH-UHFFFAOYSA-N 6-fluoropyridine Chemical compound FC1=C=CC=C[N]1 DVMILACIDBEACH-UHFFFAOYSA-N 0.000 description 1
- PJQQTVCKUXLOCR-UHFFFAOYSA-N 6-pyridin-3-yl-1h-benzimidazole Chemical compound C1=C2NC=NC2=CC=C1C1=CC=CN=C1 PJQQTVCKUXLOCR-UHFFFAOYSA-N 0.000 description 1
- YIIUXBSQHNQYQY-UHFFFAOYSA-N 6-thiophen-3-yl-1h-benzimidazole Chemical compound S1C=CC(C=2C=C3N=CNC3=CC=2)=C1 YIIUXBSQHNQYQY-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 241000114726 Acetes Species 0.000 description 1
- LIXSXTLOIVHFHV-UHFFFAOYSA-N C1CC=C(C=C1)C2=C(C=C(C=C2)Cl)Cl Chemical compound C1CC=C(C=C1)C2=C(C=C(C=C2)Cl)Cl LIXSXTLOIVHFHV-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical compound NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 1
- 125000004069 aziridinyl group Chemical group 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000005620 boronic acid group Chemical class 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 229940047583 cetamide Drugs 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- 125000005303 dithiazolyl group Chemical group S1SNC(=C1)* 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 125000002632 imidazolidinyl group Chemical group 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000003384 isochromanyl group Chemical group C1(OCCC2=CC=CC=C12)* 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- JDCQTXCGJXOJHP-UHFFFAOYSA-M lithium 2-[4-(5-phenylbenzimidazol-1-yl)phenyl]acetate Chemical compound C1(=CC=CC=C1)C1=CC2=C(N(C=N2)C2=CC=C(C=C2)CC(=O)[O-])C=C1.[Li+] JDCQTXCGJXOJHP-UHFFFAOYSA-M 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 238000005935 nucleophilic addition reaction Methods 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000005327 perimidinyl group Chemical group N1C(=NC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 125000005545 phthalimidyl group Chemical group 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000004933 β-carbolinyl group Chemical group C1(=NC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462007321P | 2014-06-03 | 2014-06-03 | |
| US62/007,321 | 2014-06-03 | ||
| PCT/US2015/033962 WO2015187818A1 (en) | 2014-06-03 | 2015-06-03 | Benzimidazole analogues and related methods |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017519818A JP2017519818A (ja) | 2017-07-20 |
| JP2017519818A5 true JP2017519818A5 (enExample) | 2018-07-19 |
| JP6612857B2 JP6612857B2 (ja) | 2019-11-27 |
Family
ID=54767311
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017516254A Active JP6612857B2 (ja) | 2014-06-03 | 2015-06-03 | ベンゾイミダゾールアナログおよび関連方法 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US9988371B2 (enExample) |
| EP (1) | EP3152194B8 (enExample) |
| JP (1) | JP6612857B2 (enExample) |
| CN (1) | CN107074778B (enExample) |
| AU (1) | AU2015271692B2 (enExample) |
| ES (1) | ES2742192T3 (enExample) |
| WO (1) | WO2015187818A1 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107176951A (zh) * | 2016-03-11 | 2017-09-19 | 恩瑞生物医药科技（上海）有限公司 | 一种脲类化合物、其制备方法及其医药用途 |
| US11603374B2 (en) | 2018-01-18 | 2023-03-14 | Array Biopharma Inc. | Substituted pyrrolo[2,3-d]pyrimidines compounds as ret kinase inhibitors |
| TW201932464A (zh) | 2018-01-18 | 2019-08-16 | 美商亞雷生物製藥股份有限公司 | 作為ret激酶抑制劑之經取代吡唑基[4,3-c]吡啶化合物 |
| US12054483B2 (en) | 2018-09-28 | 2024-08-06 | Arizona Board Of Regents On Behalf Of The University Of Arizona | Small molecule inhibitors of DYRK/CLK and uses thereof |
| WO2020168963A1 (zh) * | 2019-02-18 | 2020-08-27 | 深圳市塔吉瑞生物医药有限公司 | 取代的芳香稠合环衍生物及其组合物及用途 |
| CN113557235B (zh) * | 2019-03-06 | 2025-08-08 | C4医药公司 | 用于药物治疗的杂环化合物 |
| CN112300106B (zh) * | 2020-10-30 | 2023-03-03 | 徐州医科大学 | 一种蛋白激酶抑制剂及制备方法与应用 |
| CN112778294A (zh) * | 2021-01-07 | 2021-05-11 | 苏州安睿药业有限公司 | 5-氨基异噁唑衍生物及其在制备多激酶抑制剂中的应用 |
| CN115198256A (zh) * | 2022-07-13 | 2022-10-18 | 上海天承化学有限公司 | 一种用于聚酰亚胺薄膜的化学镀铜用还原液及其制备方法和应用 |
| WO2024206989A2 (en) * | 2023-03-30 | 2024-10-03 | Bioventures, Llc | Flt3 inhibitors and methods of using the same |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030225054A1 (en) | 2002-06-03 | 2003-12-04 | Jingwu Duan | Combined use of tace inhibitors and COX2 inhibitors as anti-inflammatory agents |
| US20050171171A1 (en) * | 2003-11-13 | 2005-08-04 | Ambit Biosciences Corporation | Amide derivatives as FLT-3 modulators |
| DOP2006000051A (es) | 2005-02-24 | 2006-08-31 | Lilly Co Eli | Inhibidores de vegf-r2 y métodos |
| GB0507575D0 (en) * | 2005-04-14 | 2005-05-18 | Novartis Ag | Organic compounds |
| CA2768638A1 (en) | 2009-08-07 | 2011-02-10 | Tibotec Pharmaceuticals | Bis-benzimidazole derivatives as hepatitis c virus inhibitors |
| UA108211C2 (uk) * | 2009-11-04 | 2015-04-10 | Янссен Рід Айрленд | Бензімідазолімідазольні похідні |
| WO2011150201A2 (en) * | 2010-05-27 | 2011-12-01 | Ambit Biosciences Corporation | Azolyl amide compounds and methods of use thereof |
| WO2012088266A2 (en) * | 2010-12-22 | 2012-06-28 | Incyte Corporation | Substituted imidazopyridazines and benzimidazoles as inhibitors of fgfr3 |
| WO2013019682A1 (en) * | 2011-07-29 | 2013-02-07 | Tempero Pharmaceuticals, Inc. | Compounds and methods |
-
2015
- 2015-06-03 JP JP2017516254A patent/JP6612857B2/ja active Active
- 2015-06-03 US US15/315,490 patent/US9988371B2/en active Active
- 2015-06-03 EP EP15802538.7A patent/EP3152194B8/en active Active
- 2015-06-03 ES ES15802538T patent/ES2742192T3/es active Active
- 2015-06-03 CN CN201580030300.7A patent/CN107074778B/zh active Active
- 2015-06-03 AU AU2015271692A patent/AU2015271692B2/en not_active Ceased
- 2015-06-03 WO PCT/US2015/033962 patent/WO2015187818A1/en not_active Ceased
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