JP2011520941A5 - - Google Patents
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- Publication number
- JP2011520941A5 JP2011520941A5 JP2011509980A JP2011509980A JP2011520941A5 JP 2011520941 A5 JP2011520941 A5 JP 2011520941A5 JP 2011509980 A JP2011509980 A JP 2011509980A JP 2011509980 A JP2011509980 A JP 2011509980A JP 2011520941 A5 JP2011520941 A5 JP 2011520941A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- carboxylic acid
- amide
- quinoxaline
- dimethoxy
- 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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- -1 amino, Monosubstituted amino Chemical group 0.000 claims 82
- 125000000217 alkyl group Chemical group 0.000 claims 56
- 150000001875 compounds Chemical class 0.000 claims 33
- 150000003839 salts Chemical class 0.000 claims 28
- 125000001424 substituent group Chemical group 0.000 claims 23
- 239000012453 solvate Substances 0.000 claims 22
- 150000001204 N-oxides Chemical class 0.000 claims 21
- 125000003545 alkoxy group Chemical group 0.000 claims 19
- 201000010099 disease Diseases 0.000 claims 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 16
- 230000001404 mediated effect Effects 0.000 claims 16
- 229910052757 nitrogen Inorganic materials 0.000 claims 16
- 239000002253 acid Substances 0.000 claims 15
- 125000001072 heteroaryl group Chemical group 0.000 claims 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 12
- 125000006413 ring segment Chemical group 0.000 claims 12
- 125000003118 aryl group Chemical group 0.000 claims 11
- 125000000623 heterocyclic group Chemical group 0.000 claims 11
- 125000003282 alkyl amino group Chemical group 0.000 claims 10
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 10
- 239000008194 pharmaceutical composition Substances 0.000 claims 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 10
- 229920006395 saturated elastomer Polymers 0.000 claims 9
- 108091008794 FGF receptors Proteins 0.000 claims 8
- 206010028980 Neoplasm Diseases 0.000 claims 8
- 201000011510 cancer Diseases 0.000 claims 8
- 102000052178 fibroblast growth factor receptor activity proteins Human genes 0.000 claims 8
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims 7
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims 6
- 239000003814 drug Substances 0.000 claims 6
- 125000001153 fluoro group Chemical group F* 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- 125000002496 methyl group Chemical group [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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 206010005003 Bladder cancer Diseases 0.000 claims 4
- 206010006187 Breast cancer Diseases 0.000 claims 4
- 208000026310 Breast neoplasm Diseases 0.000 claims 4
- 206010008342 Cervix carcinoma Diseases 0.000 claims 4
- 206010014733 Endometrial cancer Diseases 0.000 claims 4
- 206010014759 Endometrial neoplasm Diseases 0.000 claims 4
- 206010025323 Lymphomas Diseases 0.000 claims 4
- 208000034578 Multiple myelomas Diseases 0.000 claims 4
- 208000014767 Myeloproliferative disease Diseases 0.000 claims 4
- 201000007224 Myeloproliferative neoplasm Diseases 0.000 claims 4
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 4
- 208000007913 Pituitary Neoplasms Diseases 0.000 claims 4
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 4
- 206010060862 Prostate cancer Diseases 0.000 claims 4
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 4
- 208000000102 Squamous Cell Carcinoma of Head and Neck Diseases 0.000 claims 4
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 4
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 4
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 4
- 201000010881 cervical cancer Diseases 0.000 claims 4
- 239000003085 diluting agent Substances 0.000 claims 4
- 206010017758 gastric cancer Diseases 0.000 claims 4
- 208000005017 glioblastoma Diseases 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 206010073071 hepatocellular carcinoma Diseases 0.000 claims 4
- 231100000844 hepatocellular carcinoma Toxicity 0.000 claims 4
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 4
- 201000002740 oral squamous cell carcinoma Diseases 0.000 claims 4
- 201000002528 pancreatic cancer Diseases 0.000 claims 4
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 4
- 201000011549 stomach cancer Diseases 0.000 claims 4
- 201000005112 urinary bladder cancer Diseases 0.000 claims 4
- UCGPWBGSZPBDQD-UHFFFAOYSA-N 8-(2-chloro-6-fluoro-3,5-dimethoxyphenyl)-n-[5-[(4-methylpiperazin-1-yl)methyl]pyridin-2-yl]quinoxaline-5-carboxamide Chemical compound COC1=CC(OC)=C(Cl)C(C=2C3=NC=CN=C3C(C(=O)NC=3N=CC(CN4CCN(C)CC4)=CC=3)=CC=2)=C1F UCGPWBGSZPBDQD-UHFFFAOYSA-N 0.000 claims 3
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 3
- 125000001624 naphthyl group Chemical group 0.000 claims 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- AQZNNSSNBDGDFM-UHFFFAOYSA-N 8-(2,6-dichloro-3,5-dimethoxyphenyl)-N-[5-[(4-ethylpiperazin-1-yl)methyl]pyridin-2-yl]quinoxaline-5-carboxamide 8-(2,6-dichloro-3,5-dimethoxyphenyl)quinoxaline-5-carboxylic acid Chemical compound COC1=CC(OC)=C(Cl)C(C=2C3=NC=CN=C3C(C(O)=O)=CC=2)=C1Cl.C1CN(CC)CCN1CC(C=N1)=CC=C1NC(=O)C(C1=NC=CN=C11)=CC=C1C1=C(Cl)C(OC)=CC(OC)=C1Cl AQZNNSSNBDGDFM-UHFFFAOYSA-N 0.000 claims 2
- MEDCQWNTBHMAOQ-UHFFFAOYSA-N 8-(2,6-dichloro-3,5-dimethoxyphenyl)-n-[5-[(4-ethylpiperazin-1-yl)methyl]pyridin-2-yl]quinoxaline-5-carboxamide Chemical compound C1CN(CC)CCN1CC(C=N1)=CC=C1NC(=O)C(C1=NC=CN=C11)=CC=C1C1=C(Cl)C(OC)=CC(OC)=C1Cl MEDCQWNTBHMAOQ-UHFFFAOYSA-N 0.000 claims 2
- DUDZKNJTOKKCTO-UHFFFAOYSA-N 8-(2,6-dichloro-3,5-dimethoxyphenyl)-n-[5-[(dimethylamino)methyl]-1h-imidazol-2-yl]quinoxaline-5-carboxamide Chemical compound COC1=CC(OC)=C(Cl)C(C=2C3=NC=CN=C3C(C(=O)NC=3NC=C(CN(C)C)N=3)=CC=2)=C1Cl DUDZKNJTOKKCTO-UHFFFAOYSA-N 0.000 claims 2
- VPUSJEVBEOMKDF-UHFFFAOYSA-N 8-(2,6-difluoro-3,5-dimethoxyphenyl)-n-[5-[(4-ethylpiperazin-1-yl)methyl]pyridin-2-yl]quinoxaline-5-carboxamide Chemical compound C1CN(CC)CCN1CC(C=N1)=CC=C1NC(=O)C(C1=NC=CN=C11)=CC=C1C1=C(F)C(OC)=CC(OC)=C1F VPUSJEVBEOMKDF-UHFFFAOYSA-N 0.000 claims 2
- XIFFUJNWCYQIBQ-UHFFFAOYSA-N 8-(2,6-difluoro-3,5-dimethoxyphenyl)-n-[5-[(dimethylamino)methyl]-1h-imidazol-2-yl]quinoxaline-5-carboxamide Chemical compound COC1=CC(OC)=C(F)C(C=2C3=NC=CN=C3C(C(=O)NC=3NC=C(CN(C)C)N=3)=CC=2)=C1F XIFFUJNWCYQIBQ-UHFFFAOYSA-N 0.000 claims 2
- VOWUUOXGQSUEMD-UHFFFAOYSA-N 8-(2-chloro-6-fluoro-3,5-dimethoxyphenyl)-n-[5-[[2-(dimethylamino)ethyl-methylamino]methyl]pyridin-2-yl]quinoxaline-5-carboxamide Chemical compound COC1=CC(OC)=C(Cl)C(C=2C3=NC=CN=C3C(C(=O)NC=3N=CC(CN(C)CCN(C)C)=CC=3)=CC=2)=C1F VOWUUOXGQSUEMD-UHFFFAOYSA-N 0.000 claims 2
- MJWBXDNFGUSPFR-UHFFFAOYSA-N COC1=CC(OC)=C(F)C(C=2C3=NC=CN=C3C(C(O)=O)=CC=2)=C1F.COC1=CC(OC)=C(F)C(C=2C3=NC=CN=C3C(C(=O)NC=3NC=C(CN4CCN(C)CC4)N=3)=CC=2)=C1F Chemical compound COC1=CC(OC)=C(F)C(C=2C3=NC=CN=C3C(C(O)=O)=CC=2)=C1F.COC1=CC(OC)=C(F)C(C=2C3=NC=CN=C3C(C(=O)NC=3NC=C(CN4CCN(C)CC4)N=3)=CC=2)=C1F MJWBXDNFGUSPFR-UHFFFAOYSA-N 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 230000001028 anti-proliverative effect Effects 0.000 claims 2
- 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 claims 2
- 229910052796 boron Inorganic materials 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 239000003112 inhibitor Substances 0.000 claims 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 239000003909 protein kinase inhibitor Substances 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 claims 1
- CUJPFPXNDSIBPG-UHFFFAOYSA-N 1,3-propanediyl Chemical group [CH2]C[CH2] CUJPFPXNDSIBPG-UHFFFAOYSA-N 0.000 claims 1
- GWINMXPBBVWNIW-UHFFFAOYSA-N 2-[(6-aminopyridin-3-yl)methyl-methylamino]acetamide 8-(2,6-dichloro-3,5-dimethoxyphenyl)quinoxaline-5-carboxylic acid Chemical compound NC(=O)CN(C)CC1=CC=C(N)N=C1.COC1=CC(OC)=C(Cl)C(C=2C3=NC=CN=C3C(C(O)=O)=CC=2)=C1Cl GWINMXPBBVWNIW-UHFFFAOYSA-N 0.000 claims 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- BRWMCKKCXLJMDP-UHFFFAOYSA-N 4-[2-(dimethylamino)ethoxy]aniline 8-(2,6-dimethylphenyl)-N-(1H-imidazol-2-yl)quinoxaline-5-carboxamide 8-(2,6-dimethylphenyl)quinoxaline-5-carboxylic acid Chemical compound CN(C)CCOC1=CC=C(N)C=C1.CC1=CC=CC(C)=C1C1=CC=C(C(O)=O)C2=NC=CN=C12.CC1=CC=CC(C)=C1C(C1=NC=CN=C11)=CC=C1C(=O)NC1=NC=CN1 BRWMCKKCXLJMDP-UHFFFAOYSA-N 0.000 claims 1
- RHCIZBHSZJGMCC-UHFFFAOYSA-N 4-[2-(dimethylamino)ethoxy]aniline 8-(2-fluorophenyl)-N-(1H-imidazol-2-yl)quinoxaline-5-carboxamide 8-naphthalen-1-ylquinoxaline-5-carboxylic acid Chemical compound CN(C)CCOC1=CC=C(N)C=C1.C12=NC=CN=C2C(C(=O)O)=CC=C1C1=CC=CC2=CC=CC=C12.FC1=CC=CC=C1C(C1=NC=CN=C11)=CC=C1C(=O)NC1=NC=CN1 RHCIZBHSZJGMCC-UHFFFAOYSA-N 0.000 claims 1
- DMJTYXXLIPVKDL-UHFFFAOYSA-N 5-(2,6-dichloro-3,5-dimethoxyphenyl)-n-[5-[[4-[(4-methoxyphenyl)methyl]piperazin-1-yl]methyl]pyridin-2-yl]quinoline-8-carboxamide Chemical compound C1=CC(OC)=CC=C1CN1CCN(CC=2C=NC(NC(=O)C=3C4=NC=CC=C4C(C=4C(=C(OC)C=C(OC)C=4Cl)Cl)=CC=3)=CC=2)CC1 DMJTYXXLIPVKDL-UHFFFAOYSA-N 0.000 claims 1
- ANIZBTAXOVBLKR-UHFFFAOYSA-N 5-(2,6-dichloro-3,5-dimethoxyphenyl)-n-[6-[[4-[(4-methoxyphenyl)methyl]piperazin-1-yl]methyl]pyridin-3-yl]quinoline-8-carboxamide Chemical compound C1=CC(OC)=CC=C1CN1CCN(CC=2N=CC(NC(=O)C=3C4=NC=CC=C4C(C=4C(=C(OC)C=C(OC)C=4Cl)Cl)=CC=3)=CC=2)CC1 ANIZBTAXOVBLKR-UHFFFAOYSA-N 0.000 claims 1
- LYMUUHRXBLNABW-UHFFFAOYSA-N 5-(2,6-difluoro-3,5-dimethoxyphenyl)-n-[5-[(4-methylpiperazin-1-yl)methyl]pyridin-2-yl]quinoline-8-carboxamide Chemical compound COC1=CC(OC)=C(F)C(C=2C3=CC=CN=C3C(C(=O)NC=3N=CC(CN4CCN(C)CC4)=CC=3)=CC=2)=C1F LYMUUHRXBLNABW-UHFFFAOYSA-N 0.000 claims 1
- MHSKVOOFYZNTCW-UHFFFAOYSA-N 5-(2,6-difluoro-3,5-dimethoxyphenyl)quinoxaline Chemical compound FC1=C(C(=C(C=C1OC)OC)F)C=1C=CC=C2N=CC=NC=12 MHSKVOOFYZNTCW-UHFFFAOYSA-N 0.000 claims 1
- OBLLJKUAKFNLPY-UHFFFAOYSA-N 5-(diethylaminomethyl)-1H-imidazol-2-amine Chemical compound CCN(CC)CC1=CN=C(N)N1 OBLLJKUAKFNLPY-UHFFFAOYSA-N 0.000 claims 1
- HYMKMGCFRHGKLN-UHFFFAOYSA-N 5-(pyrrolidin-1-ylmethyl)pyridin-2-amine Chemical compound C1=NC(N)=CC=C1CN1CCCC1 HYMKMGCFRHGKLN-UHFFFAOYSA-N 0.000 claims 1
- AHLHYLVKABYTMZ-UHFFFAOYSA-N 5-[(3,3-difluoroazetidin-1-yl)methyl]-1H-imidazol-2-amine 8-(2,6-difluoro-3,5-dimethoxyphenyl)-N-(5-formyl-1H-imidazol-2-yl)quinoxaline-5-carboxamide Chemical compound COC(C=C(C(F)=C1C2=CC=C(C(NC3=NC(C=O)=CN3)=O)C3=NC=CN=C23)OC)=C1F.NC1=NC(CN(C2)CC2(F)F)=CN1 AHLHYLVKABYTMZ-UHFFFAOYSA-N 0.000 claims 1
- LIXUVVMNYMAAOB-UHFFFAOYSA-N 5-[(4-methylpiperazin-1-yl)methyl]-1H-imidazol-2-amine Chemical compound C1CN(C)CCN1CC1=CN=C(N)N1 LIXUVVMNYMAAOB-UHFFFAOYSA-N 0.000 claims 1
- CGKXXJLFOVLZRK-UHFFFAOYSA-N 8-(1-benzothiophen-3-yl)-N-(1H-imidazol-2-yl)quinoxaline-5-carboxamide 8-(1-benzothiophen-3-yl)-N-[5-[(4-methylpiperazin-1-yl)methyl]pyridin-2-yl]quinoxaline-5-carboxamide Chemical compound C=1C=C(C=2C3=CC=CC=C3SC=2)C2=NC=CN=C2C=1C(=O)NC1=NC=CN1.C1CN(C)CCN1CC(C=N1)=CC=C1NC(=O)C(C1=NC=CN=C11)=CC=C1C1=CSC2=CC=CC=C12 CGKXXJLFOVLZRK-UHFFFAOYSA-N 0.000 claims 1
- AXLOOZKBMVRSRM-UHFFFAOYSA-N 8-(2,6-dichloro-3,5-dimethoxyphenyl)-2-[(4-ethylpiperazin-1-yl)methyl]-n-pyridin-2-ylquinoxaline-5-carboxamide Chemical compound C1CN(CC)CCN1CC1=CN=C(C(=CC=C2C=3C(=C(OC)C=C(OC)C=3Cl)Cl)C(=O)NC=3N=CC=CC=3)C2=N1 AXLOOZKBMVRSRM-UHFFFAOYSA-N 0.000 claims 1
- UTOCNGOVOZNSQE-UHFFFAOYSA-N 8-(2,6-dichloro-3,5-dimethoxyphenyl)-2-[(4-ethylpiperazin-1-yl)methyl]-n-pyridin-3-ylquinoxaline-5-carboxamide Chemical compound C1CN(CC)CCN1CC1=CN=C(C(=CC=C2C=3C(=C(OC)C=C(OC)C=3Cl)Cl)C(=O)NC=3C=NC=CC=3)C2=N1 UTOCNGOVOZNSQE-UHFFFAOYSA-N 0.000 claims 1
- RMRAUVAJOMBYOP-UHFFFAOYSA-N 8-(2,6-dichloro-3,5-dimethoxyphenyl)-2-[2-(dimethylamino)ethyl-methylamino]-n-(1h-imidazol-2-yl)quinoxaline-5-carboxamide Chemical compound COC1=CC(OC)=C(Cl)C(C=2C3=NC(=CN=C3C(C(=O)NC=3NC=CN=3)=CC=2)N(C)CCN(C)C)=C1Cl RMRAUVAJOMBYOP-UHFFFAOYSA-N 0.000 claims 1
- MVSKVMADGSHVMB-UHFFFAOYSA-N 8-(2,6-dichloro-3,5-dimethoxyphenyl)-2-[2-(dimethylamino)ethyl-methylamino]-n-pyridin-2-ylquinoxaline-5-carboxamide Chemical compound COC1=CC(OC)=C(Cl)C(C=2C3=NC(=CN=C3C(C(=O)NC=3N=CC=CC=3)=CC=2)N(C)CCN(C)C)=C1Cl MVSKVMADGSHVMB-UHFFFAOYSA-N 0.000 claims 1
- KPGVDTIUTLRPRF-UHFFFAOYSA-N 8-(2,6-dichloro-3,5-dimethoxyphenyl)-3-[(4-ethylpiperazin-1-yl)methyl]-n-pyridin-3-ylquinoxaline-5-carboxamide Chemical compound C1CN(CC)CCN1CC1=CN=C(C(=CC=C2C(=O)NC=3C=NC=CC=3)C=3C(=C(OC)C=C(OC)C=3Cl)Cl)C2=N1 KPGVDTIUTLRPRF-UHFFFAOYSA-N 0.000 claims 1
- WANVEJFTEFRHGX-UHFFFAOYSA-N 8-(2,6-dichloro-3,5-dimethoxyphenyl)-N-[2-(4-ethylpiperazin-1-yl)pyrimidin-5-yl]quinoxaline-5-carboxamide 8-(2,6-dichloro-3,5-dimethoxyphenyl)quinoxaline-5-carboxylic acid Chemical compound COC1=CC(OC)=C(Cl)C(C=2C3=NC=CN=C3C(C(O)=O)=CC=2)=C1Cl.C1CN(CC)CCN1C(N=C1)=NC=C1NC(=O)C(C1=NC=CN=C11)=CC=C1C1=C(Cl)C(OC)=CC(OC)=C1Cl WANVEJFTEFRHGX-UHFFFAOYSA-N 0.000 claims 1
- WAQLMZYIPHQGCM-UHFFFAOYSA-N 8-(2,6-dichloro-3,5-dimethoxyphenyl)-N-[5-(diethylaminomethyl)-1H-imidazol-2-yl]quinoxaline-5-carboxamide 8-(2,6-dichloro-3,5-dimethoxyphenyl)quinoxaline-5-carboxylic acid Chemical compound COC1=CC(OC)=C(Cl)C(C=2C3=NC=CN=C3C(C(O)=O)=CC=2)=C1Cl.CCN(CC)CC1=CNC(NC(=O)C=2C3=NC=CN=C3C(C=3C(=C(OC)C=C(OC)C=3Cl)Cl)=CC=2)=N1 WAQLMZYIPHQGCM-UHFFFAOYSA-N 0.000 claims 1
- ARLDRIXWWOPQAK-UHFFFAOYSA-N 8-(2,6-dichloro-3,5-dimethoxyphenyl)-N-[5-(morpholin-4-ylmethyl)-1H-imidazol-2-yl]quinoxaline-5-carboxamide 5-[(dimethylamino)methyl]-1H-imidazol-2-amine Chemical compound CN(C)CC1=CN=C(N)N1.COC1=CC(OC)=C(Cl)C(C=2C3=NC=CN=C3C(C(=O)NC=3NC(CN4CCOCC4)=CN=3)=CC=2)=C1Cl ARLDRIXWWOPQAK-UHFFFAOYSA-N 0.000 claims 1
- IBLNQCOGDTYKJJ-UHFFFAOYSA-N 8-(2,6-dichloro-3,5-dimethoxyphenyl)-N-[5-[(dimethylamino)methyl]pyridin-2-yl]quinoxaline-5-carboxamide 5-(diethylaminomethyl)pyridin-2-amine Chemical compound CCN(CC)CC1=CC=C(N)N=C1.COC1=CC(OC)=C(Cl)C(C=2C3=NC=CN=C3C(C(=O)NC=3N=CC(CN(C)C)=CC=3)=CC=2)=C1Cl IBLNQCOGDTYKJJ-UHFFFAOYSA-N 0.000 claims 1
- AGINKNWRSHWNFS-UHFFFAOYSA-N 8-(2,6-dichloro-3,5-dimethoxyphenyl)-N-[5-[[2-(dimethylamino)ethyl-methylamino]methyl]pyridin-2-yl]quinoxaline-5-carboxamide 5-methylpyridin-2-amine Chemical compound CC1=CC=C(N)N=C1.COC1=CC(OC)=C(Cl)C(C=2C3=NC=CN=C3C(C(=O)NC=3N=CC(CN(C)CCN(C)C)=CC=3)=CC=2)=C1Cl AGINKNWRSHWNFS-UHFFFAOYSA-N 0.000 claims 1
- RACRRIGXBJIEEP-UHFFFAOYSA-N 8-(2,6-dichloro-3,5-dimethoxyphenyl)-N-[6-(4-propan-2-ylpiperazin-1-yl)pyridin-3-yl]quinoxaline-5-carboxamide 8-(2,6-dichloro-3,5-dimethoxyphenyl)quinoxaline-5-carboxylic acid Chemical compound COC1=CC(OC)=C(Cl)C(C=2C3=NC=CN=C3C(C(O)=O)=CC=2)=C1Cl.COC1=CC(OC)=C(Cl)C(C=2C3=NC=CN=C3C(C(=O)NC=3C=NC(=CC=3)N3CCN(CC3)C(C)C)=CC=2)=C1Cl RACRRIGXBJIEEP-UHFFFAOYSA-N 0.000 claims 1
- WQNLIAILEMLRSU-UHFFFAOYSA-N 8-(2,6-dichloro-3,5-dimethoxyphenyl)-n-[5-[[2-(dimethylamino)ethyl-methylamino]methyl]-1h-imidazol-2-yl]quinoxaline-5-carboxamide Chemical compound COC1=CC(OC)=C(Cl)C(C=2C3=NC=CN=C3C(C(=O)NC=3NC=C(CN(C)CCN(C)C)N=3)=CC=2)=C1Cl WQNLIAILEMLRSU-UHFFFAOYSA-N 0.000 claims 1
- RYVYVXIBDCPIBN-UHFFFAOYSA-N 8-(2,6-dichloro-3,5-dimethoxyphenyl)-n-[5-[[2-(dimethylamino)ethyl-methylamino]methyl]pyridin-2-yl]quinoxaline-5-carboxamide Chemical compound COC1=CC(OC)=C(Cl)C(C=2C3=NC=CN=C3C(C(=O)NC=3N=CC(CN(C)CCN(C)C)=CC=3)=CC=2)=C1Cl RYVYVXIBDCPIBN-UHFFFAOYSA-N 0.000 claims 1
- JVMUJWRLQAYOBW-UHFFFAOYSA-N 8-(2,6-dichloro-3,5-dimethoxyphenyl)quinoxaline-5-carboxylic acid Chemical compound COC1=CC(OC)=C(Cl)C(C=2C3=NC=CN=C3C(C(O)=O)=CC=2)=C1Cl JVMUJWRLQAYOBW-UHFFFAOYSA-N 0.000 claims 1
- RBFMBCIMUOGFKU-UHFFFAOYSA-N 8-(2,6-dichloro-3,5-dimethoxyphenyl)quinoxaline-5-carboxylic acid 2-N-methyl-2-N-(1-methylpiperidin-4-yl)pyridine-2,5-diamine Chemical compound C=1C=C(N)C=NC=1N(C)C1CCN(C)CC1.COC1=CC(OC)=C(Cl)C(C=2C3=NC=CN=C3C(C(O)=O)=CC=2)=C1Cl RBFMBCIMUOGFKU-UHFFFAOYSA-N 0.000 claims 1
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- IDRBWOHSQAANFN-UHFFFAOYSA-N 8-(2,6-dichloro-3,5-dimethoxyphenyl)quinoxaline-5-carboxylic acid 8-(2,6-dichloro-3,5-dimethoxyphenyl)-N-[5-[(2,2,4-trimethylpiperazin-1-yl)methyl]pyridin-2-yl]quinoxaline-5-carboxamide Chemical compound COC1=CC(OC)=C(Cl)C(C=2C3=NC=CN=C3C(C(O)=O)=CC=2)=C1Cl.COC1=CC(OC)=C(Cl)C(C=2C3=NC=CN=C3C(C(=O)NC=3N=CC(CN4C(CN(C)CC4)(C)C)=CC=3)=CC=2)=C1Cl IDRBWOHSQAANFN-UHFFFAOYSA-N 0.000 claims 1
- KHYNQWSNIHKEAU-UHFFFAOYSA-N 8-(2,6-dichloro-3,5-dimethoxyphenyl)quinoxaline-5-carboxylic acid 8-(2,6-dichloro-3,5-dimethoxyphenyl)-N-[5-[(3,3,4-trimethylpiperazin-1-yl)methyl]pyridin-2-yl]quinoxaline-5-carboxamide Chemical compound COC1=CC(OC)=C(Cl)C(C=2C3=NC=CN=C3C(C(O)=O)=CC=2)=C1Cl.COC1=CC(OC)=C(Cl)C(C=2C3=NC=CN=C3C(C(=O)NC=3N=CC(CN4CC(C)(C)N(C)CC4)=CC=3)=CC=2)=C1Cl KHYNQWSNIHKEAU-UHFFFAOYSA-N 0.000 claims 1
- MAFGUNKETWYPTB-UHFFFAOYSA-N 8-(2,6-dichloro-3,5-dimethoxyphenyl)quinoxaline-5-carboxylic acid 8-(2,6-dichloro-3,5-dimethoxyphenyl)-N-[6-[(3,3,4-trimethylpiperazin-1-yl)methyl]pyridin-3-yl]quinoxaline-5-carboxamide Chemical compound COC1=CC(OC)=C(Cl)C(C=2C3=NC=CN=C3C(C(O)=O)=CC=2)=C1Cl.COC1=CC(OC)=C(Cl)C(C=2C3=NC=CN=C3C(C(=O)NC=3C=NC(CN4CC(C)(C)N(C)CC4)=CC=3)=CC=2)=C1Cl MAFGUNKETWYPTB-UHFFFAOYSA-N 0.000 claims 1
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| PT2350075E (pt) | 2008-09-22 | 2014-06-09 | Array Biopharma Inc | Compostos imidazo[1,2b]piridazina substituídos como inibidores da trk cinase |
| AR077468A1 (es) | 2009-07-09 | 2011-08-31 | Array Biopharma Inc | Compuestos de pirazolo (1,5 -a) pirimidina sustituidos como inhibidores de trk- quinasa |
| GB201007286D0 (en) | 2010-04-30 | 2010-06-16 | Astex Therapeutics Ltd | New compounds |
| GB201020179D0 (en) | 2010-11-29 | 2011-01-12 | Astex Therapeutics Ltd | New compounds |
| JP6076913B2 (ja) | 2010-12-07 | 2017-02-08 | ドレクセル ユニバーシティ | 癌からの転移を阻害する方法 |
| US8754114B2 (en) | 2010-12-22 | 2014-06-17 | Incyte Corporation | Substituted imidazopyridazines and benzimidazoles as inhibitors of FGFR3 |
| US9340500B2 (en) | 2011-04-20 | 2016-05-17 | Shionogi & Co., Ltd. | Aromatic heterocyclic derivative having TRPV4-inhibiting activity |
| WO2013063003A1 (en) | 2011-10-28 | 2013-05-02 | Novartis Ag | Method of treating gastrointestinal stromal tumors |
| GB201118675D0 (en) | 2011-10-28 | 2011-12-14 | Astex Therapeutics Ltd | New compounds |
| GB201118652D0 (en) | 2011-10-28 | 2011-12-07 | Astex Therapeutics Ltd | New compounds |
| KR20140096035A (ko) | 2011-10-28 | 2014-08-04 | 노파르티스 아게 | 위장 기질 종양을 치료하는 방법 |
| GB201118656D0 (en) | 2011-10-28 | 2011-12-07 | Astex Therapeutics Ltd | New compounds |
| GB201118654D0 (en) | 2011-10-28 | 2011-12-07 | Astex Therapeutics Ltd | New compounds |
| HUE045957T2 (hu) | 2011-12-30 | 2020-01-28 | Hanmi Pharm Ind Co Ltd | Proteinkináz inhibitor hatású tieno[3,2-d]pirimidin származékok |
| GB201209609D0 (en) | 2012-05-30 | 2012-07-11 | Astex Therapeutics Ltd | New compounds |
| GB201209613D0 (en) | 2012-05-30 | 2012-07-11 | Astex Therapeutics Ltd | New compounds |
| ES2704744T3 (es) | 2012-06-13 | 2019-03-19 | Incyte Holdings Corp | Compuestos tricíclicos sustituidos como inhibidores de FGFR |
| US20150202203A1 (en) | 2012-07-11 | 2015-07-23 | Novartis Ag | Method of Treating Gastrointestinal Stromal Tumors |
| US9388185B2 (en) | 2012-08-10 | 2016-07-12 | Incyte Holdings Corporation | Substituted pyrrolo[2,3-b]pyrazines as FGFR inhibitors |
| US9266892B2 (en) | 2012-12-19 | 2016-02-23 | Incyte Holdings Corporation | Fused pyrazoles as FGFR inhibitors |
| AR094812A1 (es) | 2013-02-20 | 2015-08-26 | Eisai R&D Man Co Ltd | Derivado de piridina monocíclico como inhibidor del fgfr |
| TWI647220B (zh) | 2013-03-15 | 2019-01-11 | 美商西建卡爾有限責任公司 | 雜芳基化合物及其用途 |
| MY181020A (en) | 2013-03-15 | 2020-12-16 | Sanofi Sa | Heteroaryl compounds and uses thereof |
| EA035095B1 (ru) | 2013-04-19 | 2020-04-27 | Инсайт Холдингс Корпорейшн | Бициклические гетероциклы в качестве ингибиторов fgfr |
| GB201307577D0 (en) | 2013-04-26 | 2013-06-12 | Astex Therapeutics Ltd | New compounds |
| US10570204B2 (en) | 2013-09-26 | 2020-02-25 | The Medical College Of Wisconsin, Inc. | Methods for treating hematologic cancers |
| EP3076968B1 (en) | 2013-12-02 | 2019-04-17 | ChemoCentryx, Inc. | Ccr6 compounds |
| EP3086810A2 (en) | 2013-12-23 | 2016-11-02 | Novartis AG | Pharmaceutical combinations |
| SG10201900002QA (en) | 2014-01-24 | 2019-02-27 | Dana Farber Cancer Institue Inc | Antibody molecules to pd-1 and uses thereof |
| EP3099717B1 (en) | 2014-01-31 | 2019-03-27 | Novartis AG | Antibody molecules to tim-3 and uses thereof |
| MA38393B1 (fr) * | 2014-03-13 | 2018-11-30 | Sanofi Sa | Composés hétéroaryle et utilisations associées |
| US20150259420A1 (en) | 2014-03-14 | 2015-09-17 | Novartis Ag | Antibody molecules to lag-3 and uses thereof |
| JP6752715B2 (ja) | 2014-03-26 | 2020-09-09 | アステックス、セラピューティックス、リミテッドＡｓｔｅｘ Ｔｈｅｒａｐｅｕｔｉｃｓ Ｌｉｍｉｔｅｄ | 組合せ |
| JO3512B1 (ar) | 2014-03-26 | 2020-07-05 | Astex Therapeutics Ltd | مشتقات كينوكسالين مفيدة كمعدلات لإنزيم fgfr كيناز |
| MX373150B (es) | 2014-03-26 | 2020-04-21 | Astex Therapeutics Ltd | Combinaciones de un inhibidor del factor de crecimiento de fibroblasto (fgfr) y un inhibidor del receptor del factor de crecimiento 1 similar a insulina (igf1r). |
| KR102344105B1 (ko) | 2014-08-18 | 2021-12-29 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 모노시클릭 피리딘 유도체의 염 및 이의 결정 |
| ES2771926T3 (es) | 2014-09-13 | 2020-07-07 | Novartis Ag | Terapias de combinación |
| AU2015327868A1 (en) | 2014-10-03 | 2017-04-20 | Novartis Ag | Combination therapies |
| MA41044A (fr) | 2014-10-08 | 2017-08-15 | Novartis Ag | Compositions et procédés d'utilisation pour une réponse immunitaire accrue et traitement contre le cancer |
| TWI716362B (zh) | 2014-10-14 | 2021-01-21 | 瑞士商諾華公司 | 針對ｐｄ－ｌ１之抗體分子及其用途 |
| US10851105B2 (en) | 2014-10-22 | 2020-12-01 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| TWI719960B (zh) | 2015-02-10 | 2021-03-01 | 英商阿斯迪克治療公司 | 新穎組成物 |
| MX373169B (es) | 2015-02-20 | 2020-04-24 | Incyte Holdings Corp | Heterociclos bicíclicos como inhibidores de receptores del factor de crecimiento fibroblástico (fgfr). |
| WO2016134294A1 (en) | 2015-02-20 | 2016-08-25 | 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 |
| HK1248603A1 (zh) | 2015-03-10 | 2018-10-19 | Aduro Biotech, Inc. | 用於活化"干扰素基因的刺激剂"依懒性信号传导的组合物和方法 |
| ES2887148T3 (es) | 2015-03-25 | 2021-12-21 | Nat Cancer Ct | Agente terapéutico contra el cáncer de vías biliares |
| US10478494B2 (en) | 2015-04-03 | 2019-11-19 | Astex Therapeutics Ltd | FGFR/PD-1 combination therapy for the treatment of cancer |
| WO2017003723A1 (en) * | 2015-07-01 | 2017-01-05 | Crinetics Pharmaceuticals, Inc. | Somatostatin modulators and uses thereof |
| BR112018000808A2 (pt) | 2015-07-16 | 2018-09-04 | Array Biopharma Inc | compostos de pirazolo[1,5-a]piridina substituída como inibidores de ret cinase |
| EP3878465A1 (en) | 2015-07-29 | 2021-09-15 | Novartis AG | Combination therapies comprising antibody molecules to tim-3 |
| US20180222982A1 (en) | 2015-07-29 | 2018-08-09 | Novartis Ag | Combination therapies comprising antibody molecules to pd-1 |
| DK3317301T3 (da) | 2015-07-29 | 2021-06-28 | Immutep Sas | Kombinationsterapier omfattende antistofmolekyler mod lag-3 |
| JP2018525371A (ja) * | 2015-07-30 | 2018-09-06 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | アリール置換された二環式ヘテロアリール化合物 |
| DK3353177T3 (da) * | 2015-09-23 | 2020-08-24 | Janssen Pharmaceutica Nv | Tricykliske heterocykler til behandling af cancer |
| AU2016328693B2 (en) | 2015-09-23 | 2021-03-11 | Janssen Pharmaceutica Nv | Bi-heteroaryl substituted 1,4-benzodiazepines and uses thereof for the treatment of cancer |
| CN108697708A (zh) | 2015-10-26 | 2018-10-23 | 洛克索肿瘤学股份有限公司 | Trk抑制剂抗性癌症中的点突变以及与此相关的方法 |
| US12414945B2 (en) | 2015-12-17 | 2025-09-16 | Eisai R&D Management Co., Ltd. | Therapeutic agent for breast cancer |
| WO2017106656A1 (en) | 2015-12-17 | 2017-06-22 | Novartis Ag | Antibody molecules to pd-1 and uses thereof |
| ES2987474T3 (es) | 2016-04-04 | 2024-11-15 | Loxo Oncology Inc | Formulaciones líquidas de (S)-N-(5-((R)-2-(2,5-difluorofenil)-pirrolidin-1-IL)-pirazolo[1,5-A]pirimidin-3-IL)-3-hidroxipirrolidina-1-carboxamida |
| RS65988B1 (sr) | 2016-04-04 | 2024-10-31 | Loxo Oncology Inc | Postupak lečenja pedijatrijskih karcinoma |
| US10045991B2 (en) | 2016-04-04 | 2018-08-14 | Loxo Oncology, Inc. | Methods of treating pediatric cancers |
| ES2836222T3 (es) | 2016-05-18 | 2021-06-24 | Loxo Oncology Inc | Preparación de (S)-N-(5-((R)-2-(2,5-difluorofenil)pirrolidin-1-il)pirazolo[1,5-a]pirimidin-3-il)-3-hidroxipirrolidina-1-carboxamida |
| WO2018009466A1 (en) | 2016-07-05 | 2018-01-11 | Aduro Biotech, Inc. | Locked nucleic acid cyclic dinucleotide compounds and uses thereof |
| US20190292176A1 (en) | 2016-07-14 | 2019-09-26 | Bistol-Myers Squibb Company | Bicyclic heteroaryl substituted compounds |
| CN109689664B (zh) | 2016-07-14 | 2022-04-15 | 百时美施贵宝公司 | 作为par4抑制剂的三环杂芳基取代的喹啉和氮杂喹啉化合物 |
| KR102494647B1 (ko) | 2016-07-14 | 2023-01-31 | 브리스톨-마이어스 스큅 컴퍼니 | 비시클릭 헤테로아릴 치환된 화합물 |
| CN109803684B (zh) * | 2016-08-23 | 2022-08-23 | 卫材 R&D 管理有限公司 | 用于治疗肝细胞癌的组合疗法 |
| TWI704148B (zh) | 2016-10-10 | 2020-09-11 | 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并[1,5-a]吡啶化合物 |
| TWI752098B (zh) | 2016-10-10 | 2022-01-11 | 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并[1,5-a]吡啶化合物 |
| US10689362B2 (en) * | 2016-10-10 | 2020-06-23 | Development Center For Biotechnology | Quinoxaline compounds as type III receptor tyrosine kinase inhibitors |
| JOP20190092A1 (ar) | 2016-10-26 | 2019-04-25 | Array Biopharma Inc | عملية لتحضير مركبات بيرازولو[1، 5-a]بيريميدين وأملاح منها |
| US11168090B2 (en) | 2017-01-18 | 2021-11-09 | Array Biopharma Inc. | Substituted pyrazolo[1,5-a]pyrazines as RET kinase inhibitors |
| WO2018136663A1 (en) | 2017-01-18 | 2018-07-26 | Array Biopharma, Inc. | Ret inhibitors |
| JOP20190213A1 (ar) | 2017-03-16 | 2019-09-16 | Array Biopharma Inc | مركبات حلقية ضخمة كمثبطات لكيناز ros1 |
| UY37695A (es) | 2017-04-28 | 2018-11-30 | Novartis Ag | Compuesto dinucleótido cíclico bis 2’-5’-rr-(3’f-a)(3’f-a) y usos del mismo |
| US11267817B2 (en) | 2017-05-02 | 2022-03-08 | Drexel University | Substituted pyrrolo[1,2-a]quinoxalin-4(5H)-ones as CX3CR1 antagonists |
| AR111960A1 (es) | 2017-05-26 | 2019-09-04 | Incyte Corp | Formas cristalinas de un inhibidor de fgfr y procesos para su preparación |
| WO2018237173A1 (en) | 2017-06-22 | 2018-12-27 | Novartis Ag | Antibody molecules to cd73 and uses thereof |
| US11028068B2 (en) | 2017-07-25 | 2021-06-08 | Crinetics Pharmaceuticals, Inc. | Somatostatin modulators and uses thereof |
| TWI791053B (zh) | 2017-10-10 | 2023-02-01 | 美商亞雷生物製藥股份有限公司 | 6-(2-羥基-2-甲基丙氧基)-4-(6-(6-((6-甲氧基吡啶-3-基)甲基)-3,6-二氮雜雙環[3.1.1]庚-3-基)吡啶-3-基)吡唑并[1,5-a]吡啶-3-甲腈之結晶形式及其醫藥組合物 |
| TWI812649B (zh) | 2017-10-10 | 2023-08-21 | 美商絡速藥業公司 | 6-(2-羥基-2-甲基丙氧基)-4-(6-(6-((6-甲氧基吡啶-3-基)甲基)-3,6-二氮雜雙環[3.1.1]庚-3-基)吡啶-3-基)吡唑并[1,5-a]吡啶-3-甲腈之調配物 |
| WO2019143991A1 (en) | 2018-01-18 | 2019-07-25 | Array Biopharma Inc. | SUBSTITUTED PYRAZOLO[3,4-d]PYRIMIDINE COMPOUNDS AS RET KINASE INHIBITORS |
| EP3740491A1 (en) | 2018-01-18 | 2020-11-25 | Array Biopharma, Inc. | Substituted pyrrolo[2,3-d]pyrimidines compounds as ret kinase inhibitors |
| CN111615514B (zh) | 2018-01-18 | 2022-10-11 | 奥瑞生物药品公司 | 作为ret激酶抑制剂的取代的吡唑并[4,3-c]吡啶化合物 |
| US12398209B2 (en) | 2018-01-22 | 2025-08-26 | Janssen Biotech, Inc. | Methods of treating cancers with antagonistic anti-PD-1 antibodies |
| SG11202007591RA (en) | 2018-03-28 | 2020-09-29 | Eisai R&D Man Co Ltd | Therapeutic agent for hepatocellular carcinoma |
| CR20200590A (es) | 2018-05-04 | 2021-04-26 | Incyte Corp | Formas sólidas de un inhibidor de fgfr y procesos para prepararlas |
| MA52493A (fr) | 2018-05-04 | 2021-03-10 | Incyte Corp | Sels d'un inhibiteur de fgfr |
| AR126019A1 (es) | 2018-05-30 | 2023-09-06 | Novartis Ag | Anticuerpos frente a entpd2, terapias de combinación y métodos de uso de los anticuerpos y las terapias de combinación |
| US12109193B2 (en) | 2018-07-31 | 2024-10-08 | Loxo Oncology Inc. | Spray-dried dispersions, formulations, and polymorphs of (s)-5-amino-3-(4-((5-fluoro-2-methoxybenzamido)methyl)phenyl)-1-(1,1,1-trifluoropropan-2-yl)-1H-pyrazole-4-carboxamide |
| EP3849986B1 (en) | 2018-09-10 | 2022-06-08 | Array Biopharma, Inc. | Fused heterocyclic compounds as ret kinase inhibitors |
| WO2020131627A1 (en) | 2018-12-19 | 2020-06-25 | Array Biopharma Inc. | Substituted pyrazolo[1,5-a]pyridine compounds as inhibitors of fgfr tyrosine kinases |
| EP3898615A1 (en) | 2018-12-19 | 2021-10-27 | Array Biopharma, Inc. | 7-((3,5-dimethoxyphenyl)amino)quinoxaline derivatives as fgfr inhibitors for treating cancer |
| WO2020185532A1 (en) | 2019-03-08 | 2020-09-17 | Incyte Corporation | Methods of treating cancer with an fgfr inhibitor |
| WO2021007269A1 (en) | 2019-07-09 | 2021-01-14 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| US20220348651A1 (en) | 2019-09-18 | 2022-11-03 | Novartis Ag | Entpd2 antibodies, combination therapies, and methods of using the antibodies and combination therapies |
| WO2021067374A1 (en) | 2019-10-01 | 2021-04-08 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| TWI891666B (zh) | 2019-10-14 | 2025-08-01 | 美商英塞特公司 | 作為ｆｇｆｒ抑制劑之雙環雜環 |
| WO2021076728A1 (en) | 2019-10-16 | 2021-04-22 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| CN110840876A (zh) * | 2019-11-18 | 2020-02-28 | 青海民族大学 | 圆孢蘑菇中的没食子酸在cdc25磷酸蛋白酶上应用 |
| BR112022010664A2 (pt) | 2019-12-04 | 2022-08-16 | Incyte Corp | Derivados de um inibidor de fgfr |
| EP4069696A1 (en) | 2019-12-04 | 2022-10-12 | Incyte Corporation | Tricyclic heterocycles as fgfr inhibitors |
| IL294214B2 (en) | 2019-12-27 | 2026-04-01 | Schrodinger Inc | Cyclic compounds and methods for using them |
| WO2021146424A1 (en) | 2020-01-15 | 2021-07-22 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| CN115210226B (zh) * | 2020-02-20 | 2024-01-09 | 广州白云山医药集团股份有限公司白云山制药总厂 | 喹啉类化合物 |
| CN115485025A (zh) * | 2020-02-28 | 2022-12-16 | 雷密克斯医疗公司 | 用于调节剪接的化合物和方法 |
| CN111646945A (zh) * | 2020-05-29 | 2020-09-11 | 凯美克(上海)医药科技有限公司 | 一种4-溴-2-硝基-1h-咪唑的合成方法 |
| JP2023541047A (ja) | 2020-09-10 | 2023-09-27 | シュレーディンガー， インコーポレイテッド | がんの治療のための複素環式ペリ縮環ｃｄｃ７キナーゼ阻害剤 |
| EP4284804A1 (en) | 2021-01-26 | 2023-12-06 | Schrödinger, Inc. | Tricyclic compounds useful in the treatment of cancer, autoimmune and inflammatory disorders |
| TW202300150A (zh) | 2021-03-18 | 2023-01-01 | 美商薛定諤公司 | 環狀化合物及其使用方法 |
| TW202304459A (zh) | 2021-04-12 | 2023-02-01 | 美商英塞特公司 | 包含ｆｇｆｒ抑制劑及ｎｅｃｔｉｎ－４靶向劑之組合療法 |
| WO2022261159A1 (en) | 2021-06-09 | 2022-12-15 | Incyte Corporation | Tricyclic heterocycles as fgfr inhibitors |
| EP4352059A1 (en) | 2021-06-09 | 2024-04-17 | Incyte Corporation | Tricyclic heterocycles as fgfr inhibitors |
| CA3230256A1 (en) * | 2021-08-30 | 2023-03-09 | Dominic Reynolds | Compounds and methods for modulating splicing |
| CN114605391B (zh) * | 2022-02-21 | 2024-01-26 | 广州六顺生物科技股份有限公司 | 喹喔啉类衍生物及其制备方法和应用 |
| CN117510471B (zh) * | 2022-07-29 | 2025-02-25 | 江苏天士力帝益药业有限公司 | 一种阿贝西利的合成方法 |
| CN117865881A (zh) * | 2022-10-12 | 2024-04-12 | 重庆博腾制药科技股份有限公司 | 一种阿贝西利中间体的制备方法 |
| CN121793964A (zh) * | 2023-07-18 | 2026-04-03 | 安立玺荣生医股份有限公司 | 增强喹喔啉iii型受体酪氨酸激酶抑制剂的吸收的方法 |
| WO2025059027A1 (en) | 2023-09-11 | 2025-03-20 | Schrödinger, Inc. | Cyclopenta[e]pyrazolo[1,5-a]pyrimidine derivatives as malt1 inhibitors |
| WO2025227116A1 (en) * | 2024-04-25 | 2025-10-30 | The Board Of Regents Of The University Of Texas System | Eph-ephrin tetramerization inhibitors that target a previously unknown and very high-affinity chelator-type intermolecular protein-protein interaction |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9823871D0 (en) | 1998-10-30 | 1998-12-23 | Pharmacia & Upjohn Spa | 2-Amino-thiazole derivatives, process for their preparation, and their use as antitumour agents |
| CN1368970A (zh) * | 1999-04-06 | 2002-09-11 | 克诺尔股份有限公司 | 作为酪氨酸激酶抑制剂的取代的1,4－二氢茚并[1,2－c]吡唑 |
| GB0104422D0 (en) | 2001-02-22 | 2001-04-11 | Glaxo Group Ltd | Quinoline derivative |
| CA2446380A1 (en) | 2001-05-08 | 2002-11-14 | Yale University | Proteomimetic compounds and methods |
| WO2003007955A2 (en) | 2001-07-20 | 2003-01-30 | Cancer Research Technology Limited | Biphenyl apurinic/apyrimidinic site endonuclease inhibitors to treat cancer |
| WO2003024446A1 (en) | 2001-09-11 | 2003-03-27 | Mitsubishi Pharma Corporation | Oxidation stress inhibitor and method of measuring oxidation stress |
| EP1429765A2 (en) | 2001-09-14 | 2004-06-23 | Methylgene, Inc. | Inhibitors of histone deacetylase |
| ES2367422T3 (es) | 2001-10-09 | 2011-11-03 | Amgen Inc. | Derivados de imidazol como agentes antiinflamatorios. |
| WO2004098494A2 (en) | 2003-04-30 | 2004-11-18 | Cytokinetics, Inc. | Compounds, compositions, and methods |
| AR046845A1 (es) | 2003-11-21 | 2005-12-28 | Novartis Ag | Derivados de 1h-imidazo[4,5-c]quinolina para tratamiento de enfermedades dependientes de las proteino-quinasas |
| AU2004297235A1 (en) * | 2003-12-04 | 2005-06-23 | Vertex Pharmaceuticals Incorporated | Quinoxalines useful as inhibitors of protein kinases |
| US7501416B2 (en) | 2004-02-06 | 2009-03-10 | Bristol-Myers Squibb Company | Quinoxaline compounds and methods of using them |
| WO2005087742A1 (en) | 2004-03-08 | 2005-09-22 | Exelixis, Inc. | Metabolic kinase modulators and methods of use as pesticides |
| SE0401345D0 (sv) | 2004-05-25 | 2004-05-25 | Astrazeneca Ab | Therapeutic compounds: Pyridine as scaffold |
| US20070066646A1 (en) | 2005-08-02 | 2007-03-22 | Genmedica Therapeutics Sl | Compounds for Inhibiting Copper-Containing Amine Oxidases and Uses Thereof |
| AR058051A1 (es) | 2005-09-21 | 2008-01-23 | Astrazeneca Ab | Quinolinas de alquilnitrilo.proceso de obtencion y composiciones farmaceuticas. |
| TW200808739A (en) | 2006-04-06 | 2008-02-16 | Novartis Vaccines & Diagnostic | Quinazolines for PDK1 inhibition |
| AR066879A1 (es) * | 2007-06-08 | 2009-09-16 | Novartis Ag | Derivados de quinoxalina como inhibidores de la actividad de cinasa de tirosina de las cinasas janus |
| KR20100072090A (ko) | 2007-11-26 | 2010-06-29 | 화이자 인코포레이티드 | 5-ｌｏ 억제제로서의 피라졸 유도체 |
| US8236792B2 (en) | 2008-05-23 | 2012-08-07 | Janssen Pharmaceutica Nv | Substituted pyrrolidine amides as modulators of the histamine H3 receptor |
| BRPI0912995A2 (pt) | 2008-05-23 | 2015-10-13 | Glaxo Group Ltd | compostos tricíclicos contendo nitrogênio e sua utilização como agentes antibacterianos |
| JP5791500B2 (ja) | 2008-05-23 | 2015-10-07 | パンミラ ファーマシューティカルズ，エルエルシー． | ５−リポキシゲナーゼ活性化タンパク質阻害剤 |
| GEP20125502B (en) | 2008-05-23 | 2012-04-25 | Novartis Ag | Derivatives of quinolines and quinoxalines as protein tyrosine kinase inhibitors |
| AP2775A (en) | 2008-05-23 | 2013-09-30 | Wyeth Llc | Triazine compounds as P13 kinase and MTOR inhibitors |
-
2009
- 2009-05-20 GE GEAP200912010A patent/GEP20125502B/en unknown
- 2009-05-20 EA EA201001769A patent/EA021421B1/ru not_active IP Right Cessation
- 2009-05-20 CN CN2009801187578A patent/CN102036963B/zh not_active Expired - Fee Related
- 2009-05-20 WO PCT/EP2009/056154 patent/WO2009141386A1/en not_active Ceased
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