RU2019104092A - Производные 3-(арил или гетероарил)метилениндолин-2-она в качестве ингибиторов киназного пути раковых стволовых клеток для лечения рака - Google Patents
Производные 3-(арил или гетероарил)метилениндолин-2-она в качестве ингибиторов киназного пути раковых стволовых клеток для лечения рака Download PDFInfo
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- RU2019104092A RU2019104092A RU2019104092A RU2019104092A RU2019104092A RU 2019104092 A RU2019104092 A RU 2019104092A RU 2019104092 A RU2019104092 A RU 2019104092A RU 2019104092 A RU2019104092 A RU 2019104092A RU 2019104092 A RU2019104092 A RU 2019104092A
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- Prior art keywords
- substituted
- heterocycle
- alkyl
- aryl
- cycloalkyl
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- 125000003118 aryl group Chemical group 0.000 title claims 105
- 206010028980 Neoplasm Diseases 0.000 title claims 9
- 201000011510 cancer Diseases 0.000 title claims 9
- 210000000130 stem cell Anatomy 0.000 title claims 4
- 125000001072 heteroaryl group Chemical group 0.000 title claims 2
- 108091000080 Phosphotransferase Proteins 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 230000037361 pathway Effects 0.000 title 1
- 102000020233 phosphotransferase Human genes 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 228
- 125000000623 heterocyclic group Chemical group 0.000 claims 211
- 125000000217 alkyl group Chemical group 0.000 claims 112
- 229910052739 hydrogen Inorganic materials 0.000 claims 107
- 239000001257 hydrogen Substances 0.000 claims 107
- 125000000547 substituted alkyl group Chemical group 0.000 claims 106
- 150000002431 hydrogen Chemical class 0.000 claims 93
- 125000003107 substituted aryl group Chemical group 0.000 claims 92
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 88
- 125000000753 cycloalkyl group Chemical group 0.000 claims 87
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 83
- 229910052799 carbon Inorganic materials 0.000 claims 60
- 229910052736 halogen Inorganic materials 0.000 claims 51
- 150000002367 halogens Chemical class 0.000 claims 51
- 125000004093 cyano group Chemical group *C#N 0.000 claims 48
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 46
- 229910052757 nitrogen Inorganic materials 0.000 claims 45
- 125000003342 alkenyl group Chemical group 0.000 claims 44
- 125000000304 alkynyl group Chemical group 0.000 claims 44
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 44
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 44
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- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 11
- -1 2- (di-ethylamino) ethyl Chemical group 0.000 claims 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 10
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- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 10
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- 102000001253 Protein Kinase Human genes 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 125000003386 piperidinyl group Chemical group 0.000 claims 7
- 108060006633 protein kinase Proteins 0.000 claims 7
- 125000004953 trihalomethyl group Chemical group 0.000 claims 7
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 6
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims 6
- 150000001721 carbon Chemical group 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
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- 125000005842 heteroatom Chemical group 0.000 claims 6
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims 6
- 241000124008 Mammalia Species 0.000 claims 5
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 5
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 239000012453 solvate Substances 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- 229930192474 thiophene Natural products 0.000 claims 5
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 4
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 4
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- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 4
- 230000002401 inhibitory effect Effects 0.000 claims 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
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- 125000001424 substituent group Chemical group 0.000 claims 4
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims 3
- AMFYRKOUWBAGHV-UHFFFAOYSA-N 1h-pyrazolo[4,3-b]pyridine Chemical compound C1=CN=C2C=NNC2=C1 AMFYRKOUWBAGHV-UHFFFAOYSA-N 0.000 claims 3
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 claims 3
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- OGEBRHQLRGFBNV-RZDIXWSQSA-N chembl2036808 Chemical compound C12=NC(NCCCC)=NC=C2C(C=2C=CC(F)=CC=2)=NN1C[C@H]1CC[C@H](N)CC1 OGEBRHQLRGFBNV-RZDIXWSQSA-N 0.000 claims 3
- 150000002148 esters Chemical class 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
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- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- IJAPPYDYQCXOEF-UHFFFAOYSA-N phthalazin-1(2H)-one Chemical compound C1=CC=C2C(=O)NN=CC2=C1 IJAPPYDYQCXOEF-UHFFFAOYSA-N 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 239000000651 prodrug Substances 0.000 claims 3
- 229940002612 prodrug Drugs 0.000 claims 3
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims 3
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims 3
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims 3
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims 3
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- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims 2
- 230000003247 decreasing effect Effects 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
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- 230000033115 angiogenesis Effects 0.000 claims 1
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
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- 125000003551 oxepanyl group Chemical group 0.000 claims 1
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- CTVOZUFKICZROL-UHFFFAOYSA-N pyrrolo[3,2-b]azepine Chemical compound C1=CC=CC2=NC=CC2=N1 CTVOZUFKICZROL-UHFFFAOYSA-N 0.000 claims 1
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- 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 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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- A—HUMAN NECESSITIES
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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| CN104876928B (zh) * | 2015-05-07 | 2016-09-14 | 浙江司太立制药股份有限公司 | 7-氮杂吲哚啉-2-酮类化合物及其制备方法 |
| WO2017026119A1 (ja) * | 2015-08-10 | 2017-02-16 | 大日本住友製薬株式会社 | ５－（チアゾール－４－イル）インドリン－２－オン誘導体の精製方法 |
| CN108368108B (zh) * | 2015-11-12 | 2021-09-21 | 岭南大学研究合作基金会 | 包含作为活性成分的7-氮杂吲哚啉-2-酮衍生物或其可药用盐的药物组合物 |
| CN105461705B (zh) * | 2015-11-30 | 2018-04-10 | 中国医科大学 | 二苯并氮杂卓二酮类抗肿瘤化合物及其制备方法 |
| WO2018005444A2 (en) | 2016-06-28 | 2018-01-04 | Boston Biomedical, Inc. | Methods for treating cancer |
| CN107698593A (zh) * | 2016-08-09 | 2018-02-16 | 南京天印健华医药科技有限公司 | 作为fgfr抑制剂的杂环化合物 |
| CN106397436A (zh) * | 2016-09-06 | 2017-02-15 | 浙江司太立制药股份有限公司 | 5‑溴‑7‑氮杂吲哚啉‑2‑酮类化合物及其制备方法 |
| CN106432228A (zh) * | 2016-09-06 | 2017-02-22 | 浙江司太立制药股份有限公司 | 含有4‑肟基‑1‑哌啶基片段的7‑氮杂吲哚啉‑2‑酮类化合物及其制备方法 |
| WO2018098352A2 (en) | 2016-11-22 | 2018-05-31 | Jun Oishi | Targeting kras induced immune checkpoint expression |
| TWI830180B (zh) * | 2017-06-30 | 2024-01-21 | 財團法人工業技術研究院 | 化合物之液體劑型的醫藥配方 |
| CN110357878B (zh) * | 2018-03-26 | 2022-04-12 | 武汉誉祥医药科技有限公司 | 1,3-二氢-2H-吡咯并[3,2-b]吡啶-2-酮衍生物及其医药用途 |
| HRP20240793T1 (hr) | 2018-04-18 | 2024-09-13 | Constellation Pharmaceuticals, Inc. | Modulatori enzima koji modificiraju metil, njihovi pripravci i upotreba |
| EP3797108B1 (en) | 2018-05-21 | 2022-07-20 | Constellation Pharmaceuticals, Inc. | Modulators of methyl modifying enzymes, compositions and uses thereof |
| WO2020061232A1 (en) * | 2018-09-18 | 2020-03-26 | 1 Globe Biomedical Co., Ltd. | Treatment for non-alcoholic fatty liver disease |
| JP7589949B2 (ja) * | 2018-09-18 | 2024-11-26 | １グローブ バイオメディカル カンパニー， リミテッド | 肥満に対する処置 |
| US12435059B2 (en) * | 2019-07-03 | 2025-10-07 | The Regents Of The University Of Colorado, A Body Corporate | AMP-activated protein kinase inhibitors and methods of making and using the same |
| LT4003532T (lt) | 2019-07-24 | 2024-11-11 | Constellation Pharmaceuticals, Inc. | 7-chlor-2- (4-(3-metoksiazetidin-1-il)cikloheksil)-2,4-dimetil-n-((6-metil-4-(metiltio)-2-okso-1,2-dihidropiridin-3-il)metil)benzo[d][1,3]dioksol-5-karboksamido kristalinės formos |
| WO2021243040A2 (en) * | 2020-05-29 | 2021-12-02 | The Regents Of The University Of Michigan | Small molecule inhibitors of grk5 and grk5 subfamily members and uses thereof |
| CN111675647B (zh) * | 2020-06-26 | 2022-03-01 | 深圳技术大学 | 2-吲哚酮类pak1抑制剂及其在抗肿瘤治疗药物中的应用 |
| EP4178958A4 (en) * | 2020-07-10 | 2024-12-11 | Blossomhill Therapeutics, Inc. | MACROCYCLES AND THEIR USE |
| AU2023204770A1 (en) * | 2022-01-05 | 2024-07-18 | Blossomhill Therapeutics, Inc. | Macrocyclic compounds and use as kinase inhibitors |
| CN114213396B (zh) * | 2022-01-27 | 2023-03-24 | 深圳市乐土生物医药有限公司 | 一种吲哚-2-酮类化合物及其制备方法与用途 |
| CN117624014A (zh) * | 2022-11-02 | 2024-03-01 | 徐诺药业(南京)有限公司 | 3-(吲哚氨基)亚甲基吲哚啉类衍生物及其制备方法和应用 |
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| WO1997013767A1 (de) * | 1995-10-09 | 1997-04-17 | Chemisch Pharmazeutische Forschungsgesellschaft Mbh | Heterocyclisch substituierte 1-indolcarboxamide als cyclooxygenase-2 inhibitoren |
| GB9716557D0 (en) * | 1997-08-06 | 1997-10-08 | Glaxo Group Ltd | Benzylidene-1,3-dihydro-indol-2-one derivatives having anti-cancer activity |
| CN1136217C (zh) * | 1998-12-17 | 2004-01-28 | 霍夫曼-拉罗奇有限公司 | 作为jnk蛋白质激酶抑制剂的4-芳基羟吲哚 |
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| JP2010505859A (ja) * | 2006-10-06 | 2010-02-25 | アイアールエム・リミテッド・ライアビリティ・カンパニー | タンパク質キナーゼ阻害剤およびそれを使用するための方法 |
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| AR072538A1 (es) * | 2008-07-29 | 2010-09-01 | Boehringer Ingelheim Int | Derivados de indolinonas, composiciones farmacéuticas y usos |
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| WO2014160401A1 (en) | 2014-10-02 |
| CN105408320B (zh) | 2019-08-13 |
| JP2016513656A (ja) | 2016-05-16 |
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| AU2014243869A1 (en) | 2015-09-24 |
| SG10201806965XA (en) | 2018-09-27 |
| JP6378308B2 (ja) | 2018-08-22 |
| JP2018168187A (ja) | 2018-11-01 |
| CN105408320A (zh) | 2016-03-16 |
| EP2970206A1 (en) | 2016-01-20 |
| MX2015011456A (es) | 2016-05-31 |
| CA2904152A1 (en) | 2014-10-02 |
| AU2018233033A1 (en) | 2018-10-11 |
| HK1220184A1 (zh) | 2017-04-28 |
| BR112015022431A2 (pt) | 2017-05-09 |
| US20160031888A1 (en) | 2016-02-04 |
| IL240960A0 (en) | 2015-11-30 |
| US20190241569A1 (en) | 2019-08-08 |
| RU2015143526A (ru) | 2017-04-19 |
| SG11201507346PA (en) | 2015-10-29 |
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