JP2013530199A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2013530199A5 JP2013530199A5 JP2013517331A JP2013517331A JP2013530199A5 JP 2013530199 A5 JP2013530199 A5 JP 2013530199A5 JP 2013517331 A JP2013517331 A JP 2013517331A JP 2013517331 A JP2013517331 A JP 2013517331A JP 2013530199 A5 JP2013530199 A5 JP 2013530199A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- group
- independently
- methyl
- hydroxy
- 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.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 claims description 42
- -1 amino, aminocarbonyl Chemical group 0.000 claims description 27
- 230000010354 integration Effects 0.000 claims description 13
- 206010028980 Neoplasm Diseases 0.000 claims description 12
- 108091000080 Phosphotransferase Proteins 0.000 claims description 10
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 10
- 102000020233 phosphotransferase Human genes 0.000 claims description 10
- 230000001566 pro-viral effect Effects 0.000 claims description 10
- 206010060862 Prostate cancer Diseases 0.000 claims description 9
- 201000011510 cancer Diseases 0.000 claims description 9
- 230000000694 effects Effects 0.000 claims description 9
- 206010005003 Bladder cancer Diseases 0.000 claims description 7
- 208000026310 Breast neoplasm Diseases 0.000 claims description 7
- 206010009944 Colon cancer Diseases 0.000 claims description 7
- 208000031637 Erythroblastic Acute Leukemia Diseases 0.000 claims description 7
- 208000036566 Erythroleukaemia Diseases 0.000 claims description 7
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 7
- 208000034578 Multiple myelomas Diseases 0.000 claims description 7
- 206010033128 Ovarian cancer Diseases 0.000 claims description 7
- 206010035226 Plasma cell myeloma Diseases 0.000 claims description 7
- 208000024770 Thyroid neoplasm Diseases 0.000 claims description 7
- 208000021841 acute erythroid leukemia Diseases 0.000 claims description 7
- 201000001531 bladder carcinoma Diseases 0.000 claims description 7
- 210000000481 breast Anatomy 0.000 claims description 7
- 208000021045 exocrine pancreatic carcinoma Diseases 0.000 claims description 7
- 210000004072 lung Anatomy 0.000 claims description 7
- 201000005296 lung carcinoma Diseases 0.000 claims description 7
- 201000001441 melanoma Diseases 0.000 claims description 7
- 208000025113 myeloid leukemia Diseases 0.000 claims description 7
- 201000008968 osteosarcoma Diseases 0.000 claims description 7
- 210000000496 pancreas Anatomy 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 210000002307 prostate Anatomy 0.000 claims description 7
- 201000001514 prostate carcinoma Diseases 0.000 claims description 7
- 210000001685 thyroid gland Anatomy 0.000 claims description 7
- 210000003932 urinary bladder Anatomy 0.000 claims description 7
- 208000010570 urinary bladder carcinoma Diseases 0.000 claims description 7
- 206010006187 Breast cancer Diseases 0.000 claims description 6
- 101710182396 Fibroblast growth factor receptor 3 Proteins 0.000 claims description 6
- 102100027842 Fibroblast growth factor receptor 3 Human genes 0.000 claims description 6
- 108060006662 GSK3 Proteins 0.000 claims description 6
- 102000001267 GSK3 Human genes 0.000 claims description 6
- 101000932478 Homo sapiens Receptor-type tyrosine-protein kinase FLT3 Proteins 0.000 claims description 6
- 101150038994 PDGFRA gene Proteins 0.000 claims description 6
- 102100020718 Receptor-type tyrosine-protein kinase FLT3 Human genes 0.000 claims description 6
- 208000033781 Thyroid carcinoma Diseases 0.000 claims description 6
- 201000008275 breast carcinoma Diseases 0.000 claims description 6
- NFVJNJQRWPQVOA-UHFFFAOYSA-N n-[2-chloro-5-(trifluoromethyl)phenyl]-2-[3-(4-ethyl-5-ethylsulfanyl-1,2,4-triazol-3-yl)piperidin-1-yl]acetamide Chemical compound CCN1C(SCC)=NN=C1C1CN(CC(=O)NC=2C(=CC=C(C=2)C(F)(F)F)Cl)CCC1 NFVJNJQRWPQVOA-UHFFFAOYSA-N 0.000 claims description 6
- 210000001672 ovary Anatomy 0.000 claims description 6
- 201000002510 thyroid cancer Diseases 0.000 claims description 6
- 208000013077 thyroid gland carcinoma Diseases 0.000 claims description 6
- 206010051635 Gastrointestinal tract adenoma Diseases 0.000 claims description 4
- 108010053099 Vascular Endothelial Growth Factor Receptor-2 Proteins 0.000 claims description 3
- 108090000315 Protein Kinase C Proteins 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 32
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 22
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 22
- 229910052739 hydrogen Inorganic materials 0.000 claims 21
- 229910052805 deuterium Inorganic materials 0.000 claims 12
- 229910052736 halogen Inorganic materials 0.000 claims 12
- 150000002367 halogens Chemical class 0.000 claims 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 12
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 11
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 11
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims 11
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 11
- 125000004043 oxo group Chemical group O=* 0.000 claims 11
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 11
- 125000003545 alkoxy group Chemical group 0.000 claims 10
- 229910052799 carbon Inorganic materials 0.000 claims 10
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 9
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 9
- 125000005843 halogen group Chemical group 0.000 claims 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 8
- 125000003118 aryl group Chemical group 0.000 claims 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 7
- 229910052731 fluorine Inorganic materials 0.000 claims 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 6
- 125000000304 alkynyl group Chemical group 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 6
- 229920002554 vinyl polymer Polymers 0.000 claims 6
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims 5
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims 5
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 5
- 150000001721 carbon Chemical group 0.000 claims 5
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims 5
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 5
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical group NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 claims 5
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 claims 5
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical group C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 claims 4
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical group C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- 208000023275 Autoimmune disease Diseases 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- JMJRYTGVHCAYCT-UHFFFAOYSA-N oxan-4-one Chemical group O=C1CCOCC1 JMJRYTGVHCAYCT-UHFFFAOYSA-N 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 3
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical group C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical group C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 2
- ZCSOJXHICDKYJO-UHFFFAOYSA-N 2,3-dihydropyran-4-one Chemical compound O=C1CCOC=C1 ZCSOJXHICDKYJO-UHFFFAOYSA-N 0.000 claims 2
- BVPUSMDCHQQTJS-UHFFFAOYSA-N 3-methylideneoxan-4-ol Chemical group OC1CCOCC1=C BVPUSMDCHQQTJS-UHFFFAOYSA-N 0.000 claims 2
- 208000011231 Crohn disease Diseases 0.000 claims 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 208000037976 chronic inflammation Diseases 0.000 claims 2
- 208000037893 chronic inflammatory disorder Diseases 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
- JIDPHLLCKDISON-UHFFFAOYSA-N 2h-pyran-4-ol Chemical compound OC1=CCOC=C1 JIDPHLLCKDISON-UHFFFAOYSA-N 0.000 claims 1
- VVIAGPKUTFNRDU-UHFFFAOYSA-N 6S-folinic acid Natural products C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 VVIAGPKUTFNRDU-UHFFFAOYSA-N 0.000 claims 1
- STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 claims 1
- UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 claims 1
- 229940122029 DNA synthesis inhibitor Drugs 0.000 claims 1
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims 1
- 229940116355 PI3 kinase inhibitor Drugs 0.000 claims 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
- 229940123237 Taxane Drugs 0.000 claims 1
- 229940122803 Vinca alkaloid Drugs 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000004442 acylamino group Chemical group 0.000 claims 1
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000004682 aminothiocarbonyl group Chemical group NC(=S)* 0.000 claims 1
- 229940045799 anthracyclines and related substance Drugs 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 claims 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims 1
- 229960004562 carboplatin Drugs 0.000 claims 1
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims 1
- 229960004316 cisplatin Drugs 0.000 claims 1
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 1
- 229960004397 cyclophosphamide Drugs 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 229960000684 cytarabine Drugs 0.000 claims 1
- STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 claims 1
- 229960000975 daunorubicin Drugs 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 229960002949 fluorouracil Drugs 0.000 claims 1
- VVIAGPKUTFNRDU-ABLWVSNPSA-N folinic acid Chemical compound C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 VVIAGPKUTFNRDU-ABLWVSNPSA-N 0.000 claims 1
- 235000008191 folinic acid Nutrition 0.000 claims 1
- 239000011672 folinic acid Substances 0.000 claims 1
- SDUQYLNIPVEERB-QPPQHZFASA-N gemcitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 SDUQYLNIPVEERB-QPPQHZFASA-N 0.000 claims 1
- 229960005277 gemcitabine Drugs 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- KTUFNOKKBVMGRW-UHFFFAOYSA-N imatinib Chemical compound C1CN(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1 KTUFNOKKBVMGRW-UHFFFAOYSA-N 0.000 claims 1
- 229960004768 irinotecan Drugs 0.000 claims 1
- UWKQSNNFCGGAFS-XIFFEERXSA-N irinotecan Chemical compound C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 UWKQSNNFCGGAFS-XIFFEERXSA-N 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 229960001691 leucovorin Drugs 0.000 claims 1
- 229940124302 mTOR inhibitor Drugs 0.000 claims 1
- 239000003628 mammalian target of rapamycin inhibitor Substances 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 239000002935 phosphatidylinositol 3 kinase inhibitor Substances 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 229960004641 rituximab Drugs 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 229950006410 tezacitabine Drugs 0.000 claims 1
- GFFXZLZWLOBBLO-ASKVSEFXSA-N tezacitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(=C/F)/[C@H](O)[C@@H](CO)O1 GFFXZLZWLOBBLO-ASKVSEFXSA-N 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000003441 thioacyl group Chemical group 0.000 claims 1
- 150000003573 thiols Chemical class 0.000 claims 1
- 229960000303 topotecan Drugs 0.000 claims 1
- UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 claims 1
- 229960000575 trastuzumab Drugs 0.000 claims 1
- 238000000034 method Methods 0.000 description 15
- 102100036077 Serine/threonine-protein kinase pim-1 Human genes 0.000 description 11
- 230000002018 overexpression Effects 0.000 description 7
- 210000004027 cell Anatomy 0.000 description 5
- 108700020978 Proto-Oncogene Proteins 0.000 description 4
- 102000052575 Proto-Oncogene Human genes 0.000 description 4
- 101001001642 Xenopus laevis Serine/threonine-protein kinase pim-3 Proteins 0.000 description 4
- 230000014509 gene expression Effects 0.000 description 4
- 206010025323 Lymphomas Diseases 0.000 description 3
- 206010061902 Pancreatic neoplasm Diseases 0.000 description 3
- 101150056413 Pim1 gene Proteins 0.000 description 3
- 206010073071 hepatocellular carcinoma Diseases 0.000 description 3
- 210000000936 intestine Anatomy 0.000 description 3
- 208000032839 leukemia Diseases 0.000 description 3
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 3
- 201000002528 pancreatic cancer Diseases 0.000 description 3
- 208000009540 villous adenoma Diseases 0.000 description 3
- 101001059454 Homo sapiens Serine/threonine-protein kinase MARK2 Proteins 0.000 description 2
- 241000699660 Mus musculus Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 2
- 102100028904 Serine/threonine-protein kinase MARK2 Human genes 0.000 description 2
- 206010042971 T-cell lymphoma Diseases 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 208000032852 chronic lymphocytic leukemia Diseases 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 201000005787 hematologic cancer Diseases 0.000 description 2
- 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 description 2
- 231100000844 hepatocellular carcinoma Toxicity 0.000 description 2
- 108010083755 proto-oncogene proteins pim Proteins 0.000 description 2
- 230000001177 retroviral effect Effects 0.000 description 2
- 238000011830 transgenic mouse model Methods 0.000 description 2
- 102100031585 ADP-ribosyl cyclase/cyclic ADP-ribose hydrolase 1 Human genes 0.000 description 1
- 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 description 1
- 208000003950 B-cell lymphoma Diseases 0.000 description 1
- 208000005623 Carcinogenesis Diseases 0.000 description 1
- 101000777636 Homo sapiens ADP-ribosyl cyclase/cyclic ADP-ribose hydrolase 1 Proteins 0.000 description 1
- 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241001529936 Murinae Species 0.000 description 1
- 101100297651 Mus musculus Pim2 gene Proteins 0.000 description 1
- 101710135898 Myc proto-oncogene protein Proteins 0.000 description 1
- 102100038895 Myc proto-oncogene protein Human genes 0.000 description 1
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 description 1
- 108700020796 Oncogene Proteins 0.000 description 1
- 101150054691 PIM3 gene Proteins 0.000 description 1
- 208000008691 Precursor B-Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 description 1
- 210000001744 T-lymphocyte Anatomy 0.000 description 1
- 101710150448 Transcriptional regulator Myc Proteins 0.000 description 1
- 108700019146 Transgenes Proteins 0.000 description 1
- 102100021125 Tyrosine-protein kinase ZAP-70 Human genes 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 108010046882 ZAP-70 Protein-Tyrosine Kinase Proteins 0.000 description 1
- 230000001594 aberrant effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000006907 apoptotic process Effects 0.000 description 1
- 230000036952 cancer formation Effects 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 231100000504 carcinogenesis Toxicity 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 239000003183 carcinogenic agent Substances 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000001605 fetal effect Effects 0.000 description 1
- 230000011132 hemopoiesis Effects 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 210000002751 lymph Anatomy 0.000 description 1
- 230000036210 malignancy Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 230000002611 ovarian Effects 0.000 description 1
- 239000000092 prognostic biomarker Substances 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 201000005825 prostate adenocarcinoma Diseases 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 241001430294 unidentified retrovirus Species 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36175510P | 2010-07-06 | 2010-07-06 | |
| US61/361,755 | 2010-07-06 | ||
| PCT/EP2011/061198 WO2012004217A1 (en) | 2010-07-06 | 2011-07-04 | Cyclic ether compounds useful as kinase inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2013530199A JP2013530199A (ja) | 2013-07-25 |
| JP2013530199A5 true JP2013530199A5 (https=) | 2014-08-14 |
Family
ID=44279730
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013517331A Pending JP2013530199A (ja) | 2010-07-06 | 2011-07-04 | キナーゼ阻害剤として有用な環状エーテル化合物 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20130109682A1 (https=) |
| EP (1) | EP2590968A1 (https=) |
| JP (1) | JP2013530199A (https=) |
| CN (1) | CN103080106A (https=) |
| WO (1) | WO2012004217A1 (https=) |
Families Citing this family (97)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103619171B (zh) | 2010-11-03 | 2015-11-25 | 陶氏益农公司 | 杀虫组合物和与其相关的方法 |
| US8754114B2 (en) | 2010-12-22 | 2014-06-17 | Incyte Corporation | Substituted imidazopyridazines and benzimidazoles as inhibitors of FGFR3 |
| UY33930A (es) * | 2011-03-04 | 2012-10-31 | Novartis Ag | Inhibidores novedosos de quinasas |
| EP3812387A1 (en) | 2011-07-21 | 2021-04-28 | Sumitomo Dainippon Pharma Oncology, Inc. | Heterocyclic protein kinase inhibitors |
| JP6027128B2 (ja) | 2011-10-26 | 2016-11-16 | ダウ アグロサイエンシィズ エルエルシー | 有害生物防除組成物およびそれに関連した方法 |
| CN104822266B (zh) | 2012-04-27 | 2017-12-05 | 陶氏益农公司 | 杀虫组合物和与其相关的方法 |
| US9282739B2 (en) | 2012-04-27 | 2016-03-15 | Dow Agrosciences Llc | Pesticidal compositions and processes related thereto |
| US9708288B2 (en) | 2012-04-27 | 2017-07-18 | Dow Agrosciences Llc | Pesticidal compositions and processes related thereto |
| US9173883B2 (en) * | 2012-05-21 | 2015-11-03 | Novartis Ag | Ring-substituted N-pyridinyl amides as kinase inhibitors |
| RS58514B1 (sr) | 2012-06-13 | 2019-04-30 | Incyte Holdings Corp | Supstituisana triciklična jedinjenja kao inhibitori fgfr |
| US9388185B2 (en) | 2012-08-10 | 2016-07-12 | Incyte Holdings Corporation | Substituted pyrrolo[2,3-b]pyrazines as FGFR inhibitors |
| WO2014033630A1 (en) | 2012-08-31 | 2014-03-06 | Novartis Ag | Novel aminothiazole carboxamides as kinase inhibitors |
| WO2014033631A1 (en) | 2012-08-31 | 2014-03-06 | Novartis Ag | N-(3-pyridyl) biarylamides as kinase inhibitors |
| AU2013322736A1 (en) * | 2012-09-26 | 2015-02-26 | F. Hoffmann-La Roche Ag | Cyclic ether pyrazol-4-yl-heterocyclyl-carboxamide compounds and methods of use |
| WO2014070978A1 (en) | 2012-11-03 | 2014-05-08 | Boehringer Ingelheim International Gmbh | Inhibitors of cytomegalovirus |
| US9266892B2 (en) | 2012-12-19 | 2016-02-23 | Incyte Holdings Corporation | Fused pyrazoles as FGFR inhibitors |
| US20150336960A1 (en) | 2012-12-19 | 2015-11-26 | Novartis Ag | Aryl-substituted fused bicyclic pyridazine compounds |
| ES2649156T3 (es) | 2013-01-14 | 2018-01-10 | Incyte Holdings Corporation | Compuestos bicíclicos de carboxamida aromática útiles como inhibidores de quinasas Pim |
| PE20191245A1 (es) | 2013-01-15 | 2019-09-18 | Incyte Holdings Corp | Compuestos de tiazolcarboxamidas y piridinacarboxamida utiles como inhibidores de quinasa pim |
| PL2953942T3 (pl) | 2013-02-06 | 2018-03-30 | Bayer Cropscience Aktiengesellschaft | Podstawione halogenem pochodne pirazolu jako środki do zwalczania szkodników |
| PH12015502383B1 (en) | 2013-04-19 | 2023-02-03 | Incyte Holdings Corp | Bicyclic heterocycles as fgfr inhibitors |
| EA201690458A1 (ru) | 2013-08-23 | 2016-07-29 | Инсайт Корпорейшн | Фуро- и тиенопиридинкарбоксамиды, используемые в качестве ингибиторов pim-киназы |
| WO2015058024A1 (en) | 2013-10-17 | 2015-04-23 | Dow Agrosciences Llc | Processes for the preparation of pesticidal compounds |
| CN105636440A (zh) | 2013-10-17 | 2016-06-01 | 美国陶氏益农公司 | 制备杀虫化合物的方法 |
| US9085564B2 (en) | 2013-10-17 | 2015-07-21 | Dow Agrosciences Llc | Processes for the preparation of pesticidal compounds |
| WO2015058028A1 (en) | 2013-10-17 | 2015-04-23 | Dow Agrosciences Llc | Processes for the preparation of pesticidal compounds |
| WO2015058022A1 (en) | 2013-10-17 | 2015-04-23 | Dow Agrosciences Llc | Processes for the preparation of pesticidal compounds |
| JP2016536295A (ja) | 2013-10-17 | 2016-11-24 | ダウ アグロサイエンシィズ エルエルシー | 有害生物防除性化合物の製造方法 |
| US9174962B2 (en) | 2013-10-17 | 2015-11-03 | Dow Agrosciences Llc | Processes for the preparation of pesticidal compounds |
| MX2016005304A (es) | 2013-10-22 | 2017-03-01 | Dow Agrosciences Llc | Composiciones pesticidas sinergicas y metodos relacionados. |
| TW201517797A (zh) | 2013-10-22 | 2015-05-16 | Dow Agrosciences Llc | 協同性殺蟲組成物及相關方法（十一） |
| TW201519771A (zh) | 2013-10-22 | 2015-06-01 | Dow Agrosciences Llc | 協同性殺蟲組成物及相關方法（三） |
| CN105828608A (zh) | 2013-10-22 | 2016-08-03 | 美国陶氏益农公司 | 杀虫组合物和与其相关的方法 |
| KR20160074633A (ko) | 2013-10-22 | 2016-06-28 | 다우 아그로사이언시즈 엘엘씨 | 상승작용적 살충 조성물 및 관련 방법 |
| MX385974B (es) | 2013-10-22 | 2025-03-18 | Corteva Agriscience Llc | Composiciones pesticidas y métodos relacionados. |
| JP2016538266A (ja) | 2013-10-22 | 2016-12-08 | ダウ アグロサイエンシィズ エルエルシー | 相乗的有害生物防除組成物および関連する方法 |
| TW201519786A (zh) | 2013-10-22 | 2015-06-01 | 陶氏農業科學公司 | 殺蟲組成物及相關方法（一） |
| AU2014340437B2 (en) | 2013-10-22 | 2017-09-07 | Dow Agrosciences Llc | Synergistic pesticidal compositions and related methods |
| KR20160074640A (ko) | 2013-10-22 | 2016-06-28 | 다우 아그로사이언시즈 엘엘씨 | 살충 조성물 및 관련 방법 |
| KR20160074635A (ko) | 2013-10-22 | 2016-06-28 | 다우 아그로사이언시즈 엘엘씨 | 상승작용적 살충 조성물 및 관련 방법 |
| US9788545B2 (en) | 2013-10-22 | 2017-10-17 | Dow Agrosciences Llc | Synergistic pesticidal compositions and related methods |
| TW201519779A (zh) | 2013-10-22 | 2015-06-01 | Dow Agrosciences Llc | 協同性殺蟲組成物及相關方法（十二） |
| JP2016536307A (ja) | 2013-10-22 | 2016-11-24 | ダウ アグロサイエンシィズ エルエルシー | 農薬組成物および関連する方法 |
| US9282740B2 (en) | 2013-10-22 | 2016-03-15 | Dow Agrosciences Llc | Synergistic pesticidal compositions and related methods |
| RU2016119560A (ru) | 2013-10-22 | 2017-11-28 | ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи | Синергетические пестицидные композиции и относящиеся к ним способы |
| MX2016005317A (es) | 2013-10-22 | 2016-08-12 | Dow Agrosciences Llc | Composiciones pesticidas y metodos relacionados. |
| TW201609651A (zh) * | 2013-11-12 | 2016-03-16 | 陶氏農業科學公司 | 用於氟化化合物之過程（一） |
| EP3119775B1 (en) | 2014-03-18 | 2019-11-06 | F. Hoffmann-La Roche AG | Oxepan-2-yl-pyrazol-4-yl-heterocyclyl-carboxamide compounds and methods of use |
| US9822124B2 (en) | 2014-07-14 | 2017-11-21 | Incyte Corporation | Bicyclic heteroaromatic carboxamide compounds useful as Pim kinase inhibitors |
| US9580418B2 (en) | 2014-07-14 | 2017-02-28 | Incyte Corporation | Bicyclic aromatic carboxamide compounds useful as Pim kinase inhibitors |
| JP2017523168A (ja) | 2014-07-31 | 2017-08-17 | ダウ アグロサイエンシィズ エルエルシー | ３−（３−クロロ−１ｈ−ピラゾール−１−イル）ピリジンの製造方法 |
| BR112017000565A2 (pt) | 2014-07-31 | 2017-11-07 | Dow Agrosciences Llc | processo para a preparação de 3-(3-cloro-1h-pirazol-1-il)piridina |
| EP3174856A4 (en) | 2014-07-31 | 2018-01-10 | Dow AgroSciences LLC | Process for the preparation of 3-(3-chloro-1h-pyrazol-1-yl)pyridine |
| JO3589B1 (ar) | 2014-08-06 | 2020-07-05 | Novartis Ag | مثبطات كيناز البروتين c وطرق استخداماتها |
| EP3183238A4 (en) | 2014-08-19 | 2018-01-10 | Dow AgroSciences LLC | Process for the preparation of 3-(3-chloro-1h-pyrazol-1-yl)pyridine |
| BR112017004613A2 (pt) | 2014-09-12 | 2017-12-05 | Dow Agrosciences Llc | processo para a preparação de 3-(3-cloro-1h-pirazol-1-il)piridina |
| US10851105B2 (en) | 2014-10-22 | 2020-12-01 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| US9580423B2 (en) | 2015-02-20 | 2017-02-28 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| MA41551A (fr) | 2015-02-20 | 2017-12-26 | Incyte Corp | Hétérocycles bicycliques utilisés en tant qu'inhibiteurs de fgfr4 |
| TWI712601B (zh) | 2015-02-20 | 2020-12-11 | 美商英塞特公司 | 作為fgfr抑制劑之雙環雜環 |
| WO2016196244A1 (en) | 2015-05-29 | 2016-12-08 | Incyte Corporation | Pyridineamine compounds useful as pim kinase inhibitors |
| WO2017007756A1 (en) | 2015-07-06 | 2017-01-12 | Rodin Therapeutics, Inc | Hetero-halo inhibitors of histone deacetylase |
| EP3319968A1 (en) | 2015-07-06 | 2018-05-16 | Rodin Therapeutics, Inc. | Heterobicyclic n-aminophenyl-amides as inhibitors of histone deacetylase |
| TWI734699B (zh) | 2015-09-09 | 2021-08-01 | 美商英塞特公司 | Ｐｉｍ激酶抑制劑之鹽 |
| US9920032B2 (en) | 2015-10-02 | 2018-03-20 | Incyte Corporation | Heterocyclic compounds useful as pim kinase inhibitors |
| KR102455408B1 (ko) * | 2016-11-28 | 2022-10-14 | 브리스톨-마이어스 스큅 컴퍼니 | Gsk-3 억제제로서의 피리미딘 카르복스아미드 |
| TWI795381B (zh) | 2016-12-21 | 2023-03-11 | 比利時商健生藥品公司 | 作為ｍａｌｔ１抑制劑之吡唑衍生物 |
| WO2018125815A1 (en) | 2016-12-29 | 2018-07-05 | Dow Agrosciences Llc | Processes for the preparation of pesticidal compounds |
| CN110325036B (zh) | 2016-12-29 | 2021-10-26 | 美国陶氏益农公司 | 用于制备杀虫化合物的方法 |
| HUE057849T2 (hu) | 2017-01-11 | 2022-06-28 | Alkermes Inc | Hiszton deacetiláz biciklusos gátlói |
| US11331313B2 (en) | 2017-05-22 | 2022-05-17 | Whitehead Institute For Biomedical Research | KCC2 expression enhancing compounds and uses thereof |
| AR111960A1 (es) | 2017-05-26 | 2019-09-04 | Incyte Corp | Formas cristalinas de un inhibidor de fgfr y procesos para su preparación |
| LT3664802T (lt) | 2017-08-07 | 2022-06-27 | Alkermes, Inc. | Bicikliniai histonų deacetilazės inhibitoriai |
| WO2019113487A1 (en) | 2017-12-08 | 2019-06-13 | Incyte Corporation | Low dose combination therapy for treatment of myeloproliferative neoplasms |
| JP2021521170A (ja) | 2018-04-13 | 2021-08-26 | スミトモ ダイニッポン ファーマ オンコロジー， インコーポレイテッド | 骨髄増殖性新生物およびがんに関連する線維症の処置のためのｐｉｍキナーゼ阻害剤 |
| AU2019262579B2 (en) | 2018-05-04 | 2024-09-12 | Incyte Corporation | Salts of an FGFR inhibitor |
| US12522587B2 (en) | 2018-05-04 | 2026-01-13 | Remedy Plan, Inc. | Cancer treatments targeting cancer stem cells |
| HRP20241288T1 (hr) | 2018-05-04 | 2024-12-06 | Incyte Corporation | Čvrsti oblici fgfr inhibitora i postupci za njihovu proizvodnju |
| KR20260008165A (ko) | 2019-02-12 | 2026-01-15 | 스미토모 파마 아메리카, 인크. | 헤테로시클릭 단백질 키나제 억제제를 포함하는 제제 |
| US11628162B2 (en) | 2019-03-08 | 2023-04-18 | Incyte Corporation | Methods of treating cancer with an FGFR inhibitor |
| EP3953345B1 (en) * | 2019-04-11 | 2023-04-05 | Janssen Pharmaceutica NV | Pyridine rings containing derivatives as malt1 inhibitors |
| US11591329B2 (en) | 2019-07-09 | 2023-02-28 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
| US20220289679A1 (en) * | 2019-07-29 | 2022-09-15 | Takeda Pharmaceutical Company Limited | Heterocyclic compound |
| WO2021067374A1 (en) | 2019-10-01 | 2021-04-08 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| CA3157361A1 (en) | 2019-10-14 | 2021-04-22 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| WO2021076728A1 (en) | 2019-10-16 | 2021-04-22 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| EP4055008A1 (en) | 2019-11-06 | 2022-09-14 | Remedy Plan, Inc. | Cancer treatments targeting cancer stem cells |
| CN110790737B (zh) * | 2019-11-07 | 2022-07-22 | 河南中烟工业有限责任公司 | 一种2,3-二氢-3,5-二羟基-6-乙基-4h-吡喃-4-酮的制备方法 |
| CN110713476B (zh) * | 2019-11-07 | 2022-07-26 | 河南中烟工业有限责任公司 | 一种2,3-二氢-3,5-二羟基-6-甲基-4h-吡喃-4-酮的合成方法 |
| JP7832891B2 (ja) | 2019-12-04 | 2026-03-18 | インサイト・コーポレイション | Ｆｇｆｒ阻害剤の誘導体 |
| CA3163875A1 (en) | 2019-12-04 | 2021-06-10 | Incyte Corporation | Tricyclic heterocycles as fgfr inhibitors |
| US12012409B2 (en) | 2020-01-15 | 2024-06-18 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
| WO2022221170A1 (en) | 2021-04-12 | 2022-10-20 | Incyte Corporation | Combination therapy comprising an fgfr inhibitor and a nectin-4 targeting agent |
| CA3220155A1 (en) | 2021-06-09 | 2022-12-15 | Incyte Corporation | Tricyclic heterocycles as fgfr inhibitors |
| US11939331B2 (en) | 2021-06-09 | 2024-03-26 | Incyte Corporation | Tricyclic heterocycles as FGFR inhibitors |
| CN120302975A (zh) | 2022-10-31 | 2025-07-11 | 住友制药美国公司 | 治疗骨髓增生性肿瘤的pim1抑制剂 |
| EP4626878A1 (en) | 2022-12-02 | 2025-10-08 | Neumora Therapeutics, Inc. | Methods of treating neurological disorders |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5223526A (en) * | 1991-12-06 | 1993-06-29 | Monsanto Company | Pyrazole carboxanilide fungicides and use |
| GB0412072D0 (en) * | 2004-05-28 | 2004-06-30 | Syngenta Participations Ag | Chemical compounds |
| US20070254894A1 (en) * | 2006-01-10 | 2007-11-01 | Kane John L Jr | Novel small molecules with selective cytotoxicity against human microvascular endothelial cell proliferation |
| JP5182088B2 (ja) * | 2006-04-19 | 2013-04-10 | アステラス製薬株式会社 | アゾールカルボキサミド誘導体 |
| EP2078004B1 (en) * | 2006-10-31 | 2015-02-25 | Merck Sharp & Dohme Corp. | 2-aminothiazole-4-carboxylic amides as protein kinase inhibitors |
| JP5103604B2 (ja) * | 2006-10-31 | 2012-12-19 | メルク・シャープ・アンド・ドーム・コーポレーション | プロテインキナーゼ阻害剤としての２−アミノチアゾール−４−カルボン酸アミド |
| CA2679659C (en) * | 2007-03-01 | 2016-01-19 | Novartis Ag | Pim kinase inhibitors and methods of their use |
| MY150032A (en) * | 2007-07-19 | 2013-11-29 | Merck Sharp & Dohme | Heterocyclic amide compounds as protein kinase inhibitors |
| JP5349309B2 (ja) * | 2007-08-03 | 2013-11-20 | 株式会社キノファーマ | 抗ｄｎａウイルス作用を有するアニリン誘導体 |
| EP2212318B1 (en) * | 2007-10-29 | 2013-07-24 | Merck Sharp & Dohme Corp. | Thiazole derivatives as protein kinase inhibitors |
| PE20091577A1 (es) * | 2008-03-03 | 2009-11-05 | Novartis Ag | Inhibidores de cinasa pim y metodos para su uso |
| PL2344474T3 (pl) * | 2008-09-02 | 2016-03-31 | Novartis Ag | Pochodne pikolinamidu jako inhibitory kinaz |
| SG178986A1 (en) * | 2009-09-08 | 2012-04-27 | Hoffmann La Roche | 4-substituted pyridin-3-yl-carboxamide compounds and methods of use |
-
2011
- 2011-07-04 US US13/807,993 patent/US20130109682A1/en not_active Abandoned
- 2011-07-04 CN CN2011800335423A patent/CN103080106A/zh active Pending
- 2011-07-04 EP EP11729624.4A patent/EP2590968A1/en not_active Withdrawn
- 2011-07-04 JP JP2013517331A patent/JP2013530199A/ja active Pending
- 2011-07-04 WO PCT/EP2011/061198 patent/WO2012004217A1/en not_active Ceased
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2013530199A5 (https=) | ||
| JP2011513363A5 (https=) | ||
| AU2022204166B2 (en) | 2-aminopyrimidin-6-ones and analogs exhibiting anti-cancer and anti-proliferative activities | |
| Miller et al. | MEK1/2 inhibitors in the treatment of gynecologic malignancies | |
| WO2024169914A1 (en) | Tricyclic compounds for the treatment of cancer | |
| KR101701549B1 (ko) | 항종양 효과 증강제 | |
| AU2013225737B2 (en) | Serine/threonine kinase inhibitors | |
| ES2562306T3 (es) | Inhibidores de Pim cinasas y métodos para su uso | |
| DK2344474T3 (en) | Picolinamidderivater as kinase inhibitors | |
| EP2861585B1 (en) | Novel ring-substituted n-pyridinyl amides as kinase inhibitors | |
| JP2020503247A5 (https=) | ||
| JP2008528467A5 (https=) | ||
| JP2014527082A5 (https=) | ||
| JP2008505167A5 (https=) | ||
| JP2009543771A5 (https=) | ||
| TWI824010B (zh) | 治療血癌之組合療法 | |
| JP2013522292A5 (https=) | ||
| JP2016513660A5 (https=) | ||
| EP2681195A1 (en) | Novel kinase inhibitors | |
| JP2015528022A5 (https=) | ||
| WO2012139930A1 (en) | Pyrazolyl-pyrimidine derivatives as kinase inhibitors | |
| JP2010538091A5 (https=) | ||
| WO2014022117A1 (en) | Substituted pyrazolone compounds and methods of use | |
| JP2011506402A5 (https=) | ||
| TN2012000110A1 (en) | N-4 ( - ( ( 3- ( 2 -amino-4 pyrimidinyl) -2 -pyridinyl) oxy) phenyl) -4- (4-methyl-2-thienyl) -1-phthalazinamine for use in the treatment of antimitotic agent resistant cancer |