JP2012500277A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2012500277A5 JP2012500277A5 JP2011523939A JP2011523939A JP2012500277A5 JP 2012500277 A5 JP2012500277 A5 JP 2012500277A5 JP 2011523939 A JP2011523939 A JP 2011523939A JP 2011523939 A JP2011523939 A JP 2011523939A JP 2012500277 A5 JP2012500277 A5 JP 2012500277A5
- Authority
- JP
- Japan
- Prior art keywords
- pyridin
- triazolo
- alkyl
- yloxy
- quinoline
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 125000000217 alkyl group Chemical group 0.000 claims description 178
- 150000001875 compounds Chemical class 0.000 claims description 95
- 229910052731 fluorine Inorganic materials 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 19
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 18
- 229910052794 bromium Inorganic materials 0.000 claims description 16
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
- 208000027866 inflammatory disease Diseases 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 208000023275 Autoimmune disease Diseases 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 6
- 241000124008 Mammalia Species 0.000 claims description 5
- 206010028980 Neoplasm Diseases 0.000 claims description 5
- 201000011510 cancer Diseases 0.000 claims description 5
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 206010025135 lupus erythematosus Diseases 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 201000006417 multiple sclerosis Diseases 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 4
- 101100297651 Mus musculus Pim2 gene Proteins 0.000 claims description 3
- 101001001642 Xenopus laevis Serine/threonine-protein kinase pim-3 Proteins 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 230000002757 inflammatory effect Effects 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 239000007822 coupling agent Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 239000003446 ligand Substances 0.000 claims description 2
- 230000001404 mediated effect Effects 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 12
- 239000000203 mixture Substances 0.000 claims 10
- CBZNDVANLGVAAJ-UHFFFAOYSA-N 8-(5-fluoroazepan-4-yl)oxy-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound FC1CCNCCC1OC1=CC=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C12 CBZNDVANLGVAAJ-UHFFFAOYSA-N 0.000 claims 5
- -1 2- (7- (Aminomethyl)-[1,2,4] triazolo [4,3-a] pyridin-3-yl) quinolin-8-yloxy Chemical group 0.000 claims 4
- RLLPNDJFSFUZLM-SJLPKXTDSA-N 8-[(4r,5r)-5-fluoro-1-methylazepan-4-yl]oxy-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound C1CN(C)CC[C@@H](F)[C@@H]1OC1=CC=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C12 RLLPNDJFSFUZLM-SJLPKXTDSA-N 0.000 claims 4
- FMCHSBJRGSMUTQ-UHFFFAOYSA-N 8-(azepan-4-yloxy)-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound C1CCNCCC1OC1=CC=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C12 FMCHSBJRGSMUTQ-UHFFFAOYSA-N 0.000 claims 3
- ZXQIHLJIAWEHOF-GDBMZVCRSA-N 8-[(3r,4r)-3-fluoropiperidin-4-yl]oxy-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound F[C@@H]1CNCC[C@H]1OC1=CC=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C12 ZXQIHLJIAWEHOF-GDBMZVCRSA-N 0.000 claims 3
- ZXQIHLJIAWEHOF-ZBFHGGJFSA-N 8-[(3r,4s)-3-fluoropiperidin-4-yl]oxy-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound F[C@@H]1CNCC[C@@H]1OC1=CC=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C12 ZXQIHLJIAWEHOF-ZBFHGGJFSA-N 0.000 claims 3
- HLVXBQWAULZBSW-UHFFFAOYSA-N 2-[4-fluoro-4-[[2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]oxymethyl]piperidin-1-yl]ethanol Chemical compound C1CN(CCO)CCC1(F)COC1=CC=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C12 HLVXBQWAULZBSW-UHFFFAOYSA-N 0.000 claims 2
- RMWWTXNOTVLFAD-SJLPKXTDSA-N 8-[(4r,5r)-5-fluoroazepan-4-yl]oxy-2-(6-methyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound N12C=C(C)C=CC2=NN=C1C(N=C12)=CC=C1C=CC=C2O[C@@H]1CCNCC[C@H]1F RMWWTXNOTVLFAD-SJLPKXTDSA-N 0.000 claims 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 2
- LIVUQZJIYLMRNO-YSSOQSIOSA-N (2r)-2-ethyl-3-[2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]oxybutan-1-amine Chemical compound C1=CC=CN2C(C3=CC=C4C=CC=C(C4=N3)OC(C)[C@@H](CN)CC)=NN=C21 LIVUQZJIYLMRNO-YSSOQSIOSA-N 0.000 claims 1
- UZUNZLBTOKJXFM-VTBWFHPJSA-N (2r)-2-ethyl-3-[2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]oxyhexan-1-amine Chemical compound C1=CC=CN2C(C3=CC=C4C=CC=C(C4=N3)OC(CCC)[C@H](CC)CN)=NN=C21 UZUNZLBTOKJXFM-VTBWFHPJSA-N 0.000 claims 1
- AZSRVVPUAZTMAY-NNJIEVJOSA-N (2r)-2-ethyl-3-[2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]oxypentan-1-amine Chemical compound C1=CC=CN2C(C3=CC=C4C=CC=C(C4=N3)OC(CC)[C@@H](CN)CC)=NN=C21 AZSRVVPUAZTMAY-NNJIEVJOSA-N 0.000 claims 1
- BJSRODNZIHDLGO-KRWDZBQOSA-N (2r)-3,3-dimethyl-4-[2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]oxybutane-1,2-diol Chemical compound C1=CC=CN2C(C3=CC=C4C=CC=C(C4=N3)OCC(C)(C)[C@@H](O)CO)=NN=C21 BJSRODNZIHDLGO-KRWDZBQOSA-N 0.000 claims 1
- VMKWYFBQMNYWFN-KRWDZBQOSA-N (2r)-4-[6-fluoro-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]oxy-3,3-dimethylbutane-1,2-diol Chemical compound C1=CC=CN2C(C3=CC=C4C=C(F)C=C(C4=N3)OCC(C)(C)[C@@H](O)CO)=NN=C21 VMKWYFBQMNYWFN-KRWDZBQOSA-N 0.000 claims 1
- LIVUQZJIYLMRNO-LOACHALJSA-N (2s)-2-ethyl-3-[2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]oxybutan-1-amine Chemical compound C1=CC=CN2C(C3=CC=C4C=CC=C(C4=N3)OC(C)[C@H](CN)CC)=NN=C21 LIVUQZJIYLMRNO-LOACHALJSA-N 0.000 claims 1
- UZUNZLBTOKJXFM-UCFFOFKASA-N (2s)-2-ethyl-3-[2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]oxyhexan-1-amine Chemical compound C1=CC=CN2C(C3=CC=C4C=CC=C(C4=N3)OC(CCC)[C@@H](CC)CN)=NN=C21 UZUNZLBTOKJXFM-UCFFOFKASA-N 0.000 claims 1
- AZSRVVPUAZTMAY-BUSXIPJBSA-N (2s)-2-ethyl-3-[2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]oxypentan-1-amine Chemical compound C1=CC=CN2C(C3=CC=C4C=CC=C(C4=N3)OC(CC)[C@H](CN)CC)=NN=C21 AZSRVVPUAZTMAY-BUSXIPJBSA-N 0.000 claims 1
- JYWJWQPTFSAQOO-HKUYNNGSSA-N (2s,4s)-1-[(2-methylpropan-2-yl)oxycarbonyl]-4-[2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]oxypiperidine-2-carboxylic acid Chemical compound C1[C@@H](C(O)=O)N(C(=O)OC(C)(C)C)CC[C@@H]1OC1=CC=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C12 JYWJWQPTFSAQOO-HKUYNNGSSA-N 0.000 claims 1
- NXZWFFIZPRXGPO-WMZOPIPTSA-N (2s,4s)-n,n-dimethyl-4-[2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]oxypiperidine-2-carboxamide Chemical compound C1CN[C@H](C(=O)N(C)C)C[C@H]1OC1=CC=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C12 NXZWFFIZPRXGPO-WMZOPIPTSA-N 0.000 claims 1
- SZEWRLXOHSKGEK-WMZOPIPTSA-N (2s,4s)-n-methoxy-n-methyl-4-[2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]oxypiperidine-2-carboxamide Chemical compound C1CN[C@H](C(=O)N(C)OC)C[C@H]1OC1=CC=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C12 SZEWRLXOHSKGEK-WMZOPIPTSA-N 0.000 claims 1
- BXMIWWRRFNMNOL-UHFFFAOYSA-N 1-benzyl-4-[[2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]oxymethyl]piperidin-4-ol Chemical compound C1CC(O)(COC=2C3=NC(=CC=C3C=CC=2)C=2N3C=CC=CC3=NN=2)CCN1CC1=CC=CC=C1 BXMIWWRRFNMNOL-UHFFFAOYSA-N 0.000 claims 1
- AVHYIXDAOCBQIU-UHFFFAOYSA-N 2,2-difluoro-3-[2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]oxypropan-1-amine Chemical compound C1=CC=CN2C(C3=CC=C4C=CC=C(C4=N3)OCC(F)(F)CN)=NN=C21 AVHYIXDAOCBQIU-UHFFFAOYSA-N 0.000 claims 1
- LLCBENGUWIODIZ-UHFFFAOYSA-N 2,2-dimethyl-3-[2-(6-phenyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]oxypropan-1-amine Chemical compound N1=C2C(OCC(C)(CN)C)=CC=CC2=CC=C1C(N1C=2)=NN=C1C=CC=2C1=CC=CC=C1 LLCBENGUWIODIZ-UHFFFAOYSA-N 0.000 claims 1
- PDRMZIBUTGMDNS-UHFFFAOYSA-N 2,2-dimethyl-3-[2-(7-methyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]oxypropan-1-amine Chemical compound C1=CC=C(OCC(C)(C)CN)C2=NC(C=3N4C=CC(=CC4=NN=3)C)=CC=C21 PDRMZIBUTGMDNS-UHFFFAOYSA-N 0.000 claims 1
- KRBNQISTMITIOJ-UHFFFAOYSA-N 2,2-dimethyl-3-[2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]oxy-n-(2,2,2-trifluoroethyl)propan-1-amine Chemical compound C1=CC=CN2C(C3=CC=C4C=CC=C(C4=N3)OCC(C)(CNCC(F)(F)F)C)=NN=C21 KRBNQISTMITIOJ-UHFFFAOYSA-N 0.000 claims 1
- WEOAONDYUSMONB-UHFFFAOYSA-N 2,2-dimethyl-3-[2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]oxypropan-1-amine Chemical compound C1=CC=CN2C(C3=CC=C4C=CC=C(C4=N3)OCC(C)(CN)C)=NN=C21 WEOAONDYUSMONB-UHFFFAOYSA-N 0.000 claims 1
- QDMRXIVSBQLTQK-UHFFFAOYSA-N 2,2-dimethyl-3-[2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]oxypropan-1-ol Chemical compound C1=CC=CN2C(C3=CC=C4C=CC=C(C4=N3)OCC(C)(CO)C)=NN=C21 QDMRXIVSBQLTQK-UHFFFAOYSA-N 0.000 claims 1
- GFKGJYLACPSTJU-ZBFHGGJFSA-N 2-(6-bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)-8-[(3r,4s)-3-fluoropiperidin-4-yl]oxyquinoline Chemical compound F[C@@H]1CNCC[C@@H]1OC1=CC=CC2=CC=C(C=3N4C=C(Br)C=CC4=NN=3)N=C12 GFKGJYLACPSTJU-ZBFHGGJFSA-N 0.000 claims 1
- HXQPFMKSDOZAOU-UHFFFAOYSA-N 2-(6-bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)-8-[(4-fluoropiperidin-4-yl)methoxy]quinoline Chemical compound C=1C=CC2=CC=C(C=3N4C=C(Br)C=CC4=NN=3)N=C2C=1OCC1(F)CCNCC1 HXQPFMKSDOZAOU-UHFFFAOYSA-N 0.000 claims 1
- MIOMGNNEGLSKDE-MJGOQNOKSA-N 2-(6-cyclopropyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)-8-[(3r,4s)-3-fluoropiperidin-4-yl]oxyquinoline Chemical compound F[C@@H]1CNCC[C@@H]1OC1=CC=CC2=CC=C(C=3N4C=C(C=CC4=NN=3)C3CC3)N=C12 MIOMGNNEGLSKDE-MJGOQNOKSA-N 0.000 claims 1
- LUTLMEWAYGPCHC-UHFFFAOYSA-N 2-(6-cyclopropyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)-8-[(4-fluoropiperidin-4-yl)methoxy]quinoline Chemical compound C=1C=CC2=CC=C(C=3N4C=C(C=CC4=NN=3)C3CC3)N=C2C=1OCC1(F)CCNCC1 LUTLMEWAYGPCHC-UHFFFAOYSA-N 0.000 claims 1
- ABZNMUCRZXRUAU-UYAOXDASSA-N 2-(6-cyclopropyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)-8-[(4r,5r)-5-fluoroazepan-4-yl]oxyquinoline Chemical compound F[C@@H]1CCNCC[C@H]1OC1=CC=CC2=CC=C(C=3N4C=C(C=CC4=NN=3)C3CC3)N=C12 ABZNMUCRZXRUAU-UYAOXDASSA-N 0.000 claims 1
- PHJNQZCUTKCIGD-ZBFHGGJFSA-N 2-(7-chloro-[1,2,4]triazolo[4,3-a]pyridin-3-yl)-8-[(3r,4s)-3-fluoropiperidin-4-yl]oxyquinoline Chemical compound F[C@@H]1CNCC[C@@H]1OC1=CC=CC2=CC=C(C=3N4C=CC(Cl)=CC4=NN=3)N=C12 PHJNQZCUTKCIGD-ZBFHGGJFSA-N 0.000 claims 1
- QYVMBCOLWIDSKD-UHFFFAOYSA-N 2-(7-methoxy-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-ol Chemical compound C1=CC=C(O)C2=NC(C=3N4C=CC(=CC4=NN=3)OC)=CC=C21 QYVMBCOLWIDSKD-UHFFFAOYSA-N 0.000 claims 1
- RICVCTVAFYHJNC-UHFFFAOYSA-N 2-[4-[[6-fluoro-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]oxymethyl]-4-methoxyazepan-1-yl]ethanol Chemical compound C=1C(F)=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C2C=1OCC1(OC)CCCN(CCO)CC1 RICVCTVAFYHJNC-UHFFFAOYSA-N 0.000 claims 1
- PQACSMVQKDXJMY-UHFFFAOYSA-N 2-[4-fluoro-4-[[2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]oxymethyl]piperidin-1-yl]acetamide Chemical compound C1CN(CC(=O)N)CCC1(F)COC1=CC=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C12 PQACSMVQKDXJMY-UHFFFAOYSA-N 0.000 claims 1
- SETJHBISTGDOHI-UHFFFAOYSA-N 2-[7-(2-methoxyethoxy)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]quinolin-8-ol Chemical compound C1=CC=C(O)C2=NC(C=3N4C=CC(=CC4=NN=3)OCCOC)=CC=C21 SETJHBISTGDOHI-UHFFFAOYSA-N 0.000 claims 1
- UKOFGJPVBBRSGO-UHFFFAOYSA-N 2-[[2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]oxymethyl]butan-1-ol Chemical compound C1=CC=CN2C(C3=CC=C4C=CC=C(C4=N3)OCC(CO)CC)=NN=C21 UKOFGJPVBBRSGO-UHFFFAOYSA-N 0.000 claims 1
- LHKDWQFFBVATPU-UHFFFAOYSA-N 2-[[2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]oxymethyl]morpholine Chemical compound C=1C=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C2C=1OCC1CNCCO1 LHKDWQFFBVATPU-UHFFFAOYSA-N 0.000 claims 1
- JMXDXNXSONBWNR-UHFFFAOYSA-N 2-ethyl-2-[[2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]oxymethyl]butan-1-ol Chemical compound C1=CC=CN2C(C3=CC=C4C=CC=C(C4=N3)OCC(CC)(CO)CC)=NN=C21 JMXDXNXSONBWNR-UHFFFAOYSA-N 0.000 claims 1
- QZYGPBINVRPXPJ-UHFFFAOYSA-N 3,3-dimethyl-4-[2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]oxybutan-1-amine Chemical compound C1=CC=CN2C(C3=CC=C4C=CC=C(C4=N3)OCC(C)(CCN)C)=NN=C21 QZYGPBINVRPXPJ-UHFFFAOYSA-N 0.000 claims 1
- YRYBUDFRAMZDPV-UHFFFAOYSA-N 3-[2-(6-bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]oxy-2,2-dimethylpropan-1-amine Chemical compound C1=CC(Br)=CN2C(C3=CC=C4C=CC=C(C4=N3)OCC(C)(CN)C)=NN=C21 YRYBUDFRAMZDPV-UHFFFAOYSA-N 0.000 claims 1
- DPNYLXBQKCMOTA-UHFFFAOYSA-N 3-[2-(6-cyclopropyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]oxy-2,2-dimethylpropan-1-amine Chemical compound N1=C2C(OCC(C)(CN)C)=CC=CC2=CC=C1C(N1C=2)=NN=C1C=CC=2C1CC1 DPNYLXBQKCMOTA-UHFFFAOYSA-N 0.000 claims 1
- LLIAUBZSOICLJD-UHFFFAOYSA-N 3-[2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]oxypropan-1-amine Chemical compound C1=CC=CN2C(C3=CC=C4C=CC=C(C4=N3)OCCCN)=NN=C21 LLIAUBZSOICLJD-UHFFFAOYSA-N 0.000 claims 1
- QROPNMPPKCMQAY-UHFFFAOYSA-N 3-[2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]oxypropane-1,2-diol Chemical compound C1=CC=CN2C(C3=CC=C4C=CC=C(C4=N3)OCC(O)CO)=NN=C21 QROPNMPPKCMQAY-UHFFFAOYSA-N 0.000 claims 1
- NQMGIRXTZPKONK-UHFFFAOYSA-N 3-[5-fluoro-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]oxy-2,2-dimethylpropan-1-amine Chemical compound C1=CC=CN2C(C3=CC=C4C(F)=CC=C(C4=N3)OCC(C)(CN)C)=NN=C21 NQMGIRXTZPKONK-UHFFFAOYSA-N 0.000 claims 1
- NIPDJBAMYWKEHF-UHFFFAOYSA-N 3-[6-fluoro-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]oxy-2,2-dimethylpropan-1-amine Chemical compound C1=CC=CN2C(C3=CC=C4C=C(F)C=C(C4=N3)OCC(C)(CN)C)=NN=C21 NIPDJBAMYWKEHF-UHFFFAOYSA-N 0.000 claims 1
- UHYACKXUWYSKIU-UHFFFAOYSA-N 3-[7-bromo-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]oxy-2,2-dimethylpropan-1-amine Chemical compound C1=CC=CN2C(C3=CC=C4C=CC(Br)=C(C4=N3)OCC(C)(CN)C)=NN=C21 UHYACKXUWYSKIU-UHFFFAOYSA-N 0.000 claims 1
- ZHCWTQZMKNJXSB-SJLPKXTDSA-N 3-[8-[(4r,5r)-5-fluoroazepan-4-yl]oxyquinolin-2-yl]-[1,2,4]triazolo[4,3-a]pyridine-6-carbonitrile Chemical compound F[C@@H]1CCNCC[C@H]1OC1=CC=CC2=CC=C(C=3N4C=C(C=CC4=NN=3)C#N)N=C12 ZHCWTQZMKNJXSB-SJLPKXTDSA-N 0.000 claims 1
- QTMIZGAYEHCXKL-UHFFFAOYSA-N 4-[2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]oxypiperidine-1-carboxamide Chemical compound C1CN(C(=O)N)CCC1OC1=CC=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C12 QTMIZGAYEHCXKL-UHFFFAOYSA-N 0.000 claims 1
- FCBCXLYBVJUGRO-UHFFFAOYSA-N 4-[2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]oxypyridin-2-amine Chemical compound C1=NC(N)=CC(OC=2C3=NC(=CC=C3C=CC=2)C=2N3C=CC=CC3=NN=2)=C1 FCBCXLYBVJUGRO-UHFFFAOYSA-N 0.000 claims 1
- QJQQPKWBHPFTEZ-UHFFFAOYSA-N 4-[2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]oxypyrimidin-2-amine Chemical compound NC1=NC=CC(OC=2C3=NC(=CC=C3C=CC=2)C=2N3C=CC=CC3=NN=2)=N1 QJQQPKWBHPFTEZ-UHFFFAOYSA-N 0.000 claims 1
- PKUYPRFEWPYLAU-UHFFFAOYSA-N 4-[[2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]oxymethyl]azepan-4-ol Chemical compound C=1C=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C2C=1OCC1(O)CCCNCC1 PKUYPRFEWPYLAU-UHFFFAOYSA-N 0.000 claims 1
- ILKOWNVFKVGQKA-UHFFFAOYSA-N 4-[[2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]oxymethyl]piperidin-4-ol Chemical compound C=1C=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C2C=1OCC1(O)CCNCC1 ILKOWNVFKVGQKA-UHFFFAOYSA-N 0.000 claims 1
- OIHRVTLGUCLTFU-UHFFFAOYSA-N 6-fluoro-8-[(3-fluoroazetidin-3-yl)methoxy]-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound C=12N=C(C=3N4C=CC=CC4=NN=3)C=CC2=CC(F)=CC=1OCC1(F)CNC1 OIHRVTLGUCLTFU-UHFFFAOYSA-N 0.000 claims 1
- KXDUVJWVGXIEPX-ZBFHGGJFSA-N 6-fluoro-8-[(3r,4s)-3-fluoropiperidin-4-yl]oxy-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound F[C@@H]1CNCC[C@@H]1OC1=CC(F)=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C12 KXDUVJWVGXIEPX-ZBFHGGJFSA-N 0.000 claims 1
- LSRFJFLUAZLYAC-UHFFFAOYSA-N 6-fluoro-8-[(4-fluoropiperidin-4-yl)methoxy]-2-(6-methoxy-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound N12C=C(OC)C=CC2=NN=C1C(N=C12)=CC=C1C=C(F)C=C2OCC1(F)CCNCC1 LSRFJFLUAZLYAC-UHFFFAOYSA-N 0.000 claims 1
- NQXPYPBIBFFEAE-UHFFFAOYSA-N 6-fluoro-8-[(4-fluoropiperidin-4-yl)methoxy]-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound C=12N=C(C=3N4C=CC=CC4=NN=3)C=CC2=CC(F)=CC=1OCC1(F)CCNCC1 NQXPYPBIBFFEAE-UHFFFAOYSA-N 0.000 claims 1
- JEKGYBBSKUISTO-UHFFFAOYSA-N 6-fluoro-8-[(4-methoxyazepan-4-yl)methoxy]-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound C=1C(F)=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C2C=1OCC1(OC)CCCNCC1 JEKGYBBSKUISTO-UHFFFAOYSA-N 0.000 claims 1
- SJVQOMGMHYJTEW-NVXWUHKLSA-N 6-fluoro-8-[(4r,5r)-5-fluoroazepan-4-yl]oxy-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound F[C@@H]1CCNCC[C@H]1OC1=CC(F)=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C12 SJVQOMGMHYJTEW-NVXWUHKLSA-N 0.000 claims 1
- SJVQOMGMHYJTEW-DOTOQJQBSA-N 6-fluoro-8-[(4r,5s)-5-fluoroazepan-4-yl]oxy-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound F[C@H]1CCNCC[C@H]1OC1=CC(F)=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C12 SJVQOMGMHYJTEW-DOTOQJQBSA-N 0.000 claims 1
- QBGRDZKWELBKAA-AWEZNQCLSA-N 6-fluoro-8-[[(3s)-piperidin-3-yl]methoxy]-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound C=12N=C(C=3N4C=CC=CC4=NN=3)C=CC2=CC(F)=CC=1OC[C@H]1CCCNC1 QBGRDZKWELBKAA-AWEZNQCLSA-N 0.000 claims 1
- CUWBXIFJTGMJHU-UHFFFAOYSA-N 8-(2,2-dimethylpropoxy)-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound C1=CC=CN2C(C3=CC=C4C=CC=C(C4=N3)OCC(C)(C)C)=NN=C21 CUWBXIFJTGMJHU-UHFFFAOYSA-N 0.000 claims 1
- DIIUODQRBMKWMI-UHFFFAOYSA-N 8-(2-piperidin-2-ylethoxy)-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound C=1C=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C2C=1OCCC1CCCCN1 DIIUODQRBMKWMI-UHFFFAOYSA-N 0.000 claims 1
- INYRWBVCPQQSGE-UHFFFAOYSA-N 8-(3,3-difluoropiperidin-4-yl)oxy-6-fluoro-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound C=12N=C(C=3N4C=CC=CC4=NN=3)C=CC2=CC(F)=CC=1OC1CCNCC1(F)F INYRWBVCPQQSGE-UHFFFAOYSA-N 0.000 claims 1
- KDDDVGDVYWKNOE-UHFFFAOYSA-N 8-(3-fluoroazepan-4-yl)oxy-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound FC1CNCCCC1OC1=CC=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C12 KDDDVGDVYWKNOE-UHFFFAOYSA-N 0.000 claims 1
- FUGPTCJAZZYCRJ-UHFFFAOYSA-N 8-(piperidin-3-ylmethoxy)-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound C=1C=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C2C=1OCC1CCCNC1 FUGPTCJAZZYCRJ-UHFFFAOYSA-N 0.000 claims 1
- CAZNIOSROXHNKZ-UHFFFAOYSA-N 8-(piperidin-4-ylmethoxy)-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound C=1C=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C2C=1OCC1CCNCC1 CAZNIOSROXHNKZ-UHFFFAOYSA-N 0.000 claims 1
- UDUHUPMKTQPDJW-UHFFFAOYSA-N 8-(pyridin-3-ylmethoxy)-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound C=1C=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C2C=1OCC1=CC=CN=C1 UDUHUPMKTQPDJW-UHFFFAOYSA-N 0.000 claims 1
- BRKBEUWDJQDKTM-UHFFFAOYSA-N 8-(pyridin-4-ylmethoxy)-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound C=1C=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C2C=1OCC1=CC=NC=C1 BRKBEUWDJQDKTM-UHFFFAOYSA-N 0.000 claims 1
- RYSAKMOLNKFGCG-UHFFFAOYSA-N 8-[(1-ethyl-4-fluoropiperidin-4-yl)methoxy]-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound C1CN(CC)CCC1(F)COC1=CC=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C12 RYSAKMOLNKFGCG-UHFFFAOYSA-N 0.000 claims 1
- DHICUKZZXJZLPW-UHFFFAOYSA-N 8-[(3-fluoroazetidin-3-yl)methoxy]-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound C=1C=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C2C=1OCC1(F)CNC1 DHICUKZZXJZLPW-UHFFFAOYSA-N 0.000 claims 1
- IOMPXUVGZPWQSW-UHFFFAOYSA-N 8-[(3-fluoropiperidin-3-yl)methoxy]-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound C=1C=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C2C=1OCC1(F)CCCNC1 IOMPXUVGZPWQSW-UHFFFAOYSA-N 0.000 claims 1
- RHBRUYKHEGUGEJ-CQSZACIVSA-N 8-[(3r)-pyrrolidin-3-yl]oxy-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound C1NCC[C@H]1OC1=CC=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C12 RHBRUYKHEGUGEJ-CQSZACIVSA-N 0.000 claims 1
- CTVPSIXLKPKNTQ-ZBFHGGJFSA-N 8-[(3r,4s)-3-fluoropiperidin-4-yl]oxy-2-(6-fluoro-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound F[C@@H]1CNCC[C@@H]1OC1=CC=CC2=CC=C(C=3N4C=C(F)C=CC4=NN=3)N=C12 CTVPSIXLKPKNTQ-ZBFHGGJFSA-N 0.000 claims 1
- NLZJFVXOFCFQHC-IRLDBZIGSA-N 8-[(3r,4s)-3-fluoropiperidin-4-yl]oxy-2-(6-phenyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound F[C@@H]1CNCC[C@@H]1OC1=CC=CC2=CC=C(C=3N4C=C(C=CC4=NN=3)C=3C=CC=CC=3)N=C12 NLZJFVXOFCFQHC-IRLDBZIGSA-N 0.000 claims 1
- RHBRUYKHEGUGEJ-AWEZNQCLSA-N 8-[(3s)-pyrrolidin-3-yl]oxy-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound C1NCC[C@@H]1OC1=CC=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C12 RHBRUYKHEGUGEJ-AWEZNQCLSA-N 0.000 claims 1
- HETPKWYRMKCRBF-UHFFFAOYSA-N 8-[(4-ethylpiperidin-4-yl)methoxy]-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound C=1C=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C2C=1OCC1(CC)CCNCC1 HETPKWYRMKCRBF-UHFFFAOYSA-N 0.000 claims 1
- DFPNYFLFFOGKAB-UHFFFAOYSA-N 8-[(4-fluoropiperidin-4-yl)methoxy]-2-(6-fluoro-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound N12C=C(F)C=CC2=NN=C1C(N=C12)=CC=C1C=CC=C2OCC1(F)CCNCC1 DFPNYFLFFOGKAB-UHFFFAOYSA-N 0.000 claims 1
- ALFMWZJOROWWPA-UHFFFAOYSA-N 8-[(4-fluoropiperidin-4-yl)methoxy]-2-(6-methoxy-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound N12C=C(OC)C=CC2=NN=C1C(N=C12)=CC=C1C=CC=C2OCC1(F)CCNCC1 ALFMWZJOROWWPA-UHFFFAOYSA-N 0.000 claims 1
- ABHCOFKCKYHXPW-UHFFFAOYSA-N 8-[(4-fluoropiperidin-4-yl)methoxy]-2-(6-phenyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound C=1C=CC2=CC=C(C=3N4C=C(C=CC4=NN=3)C=3C=CC=CC=3)N=C2C=1OCC1(F)CCNCC1 ABHCOFKCKYHXPW-UHFFFAOYSA-N 0.000 claims 1
- XQTDEFZROIJVJH-UHFFFAOYSA-N 8-[(4-fluoropiperidin-4-yl)methoxy]-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound C=1C=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C2C=1OCC1(F)CCNCC1 XQTDEFZROIJVJH-UHFFFAOYSA-N 0.000 claims 1
- AWBZYMVOPQLWGA-UHFFFAOYSA-N 8-[(4-fluoropiperidin-4-yl)methoxy]-2-[7-(2-methoxyethoxy)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]quinoline Chemical compound N=1N=C2C=C(OCCOC)C=CN2C=1C(N=C12)=CC=C1C=CC=C2OCC1(F)CCNCC1 AWBZYMVOPQLWGA-UHFFFAOYSA-N 0.000 claims 1
- XDNVVTNNZOBEOE-UHFFFAOYSA-N 8-[(4-methoxyazepan-4-yl)methoxy]-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound C=1C=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C2C=1OCC1(OC)CCCNCC1 XDNVVTNNZOBEOE-UHFFFAOYSA-N 0.000 claims 1
- NTFBHHYDVVRATP-UHFFFAOYSA-N 8-[(4-methoxypiperidin-4-yl)methoxy]-2-(7-methyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound C=1C=CC2=CC=C(C=3N4C=CC(C)=CC4=NN=3)N=C2C=1OCC1(OC)CCNCC1 NTFBHHYDVVRATP-UHFFFAOYSA-N 0.000 claims 1
- NNCWGHBKJIEMSS-UHFFFAOYSA-N 8-[(4-methoxypiperidin-4-yl)methoxy]-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound C=1C=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C2C=1OCC1(OC)CCNCC1 NNCWGHBKJIEMSS-UHFFFAOYSA-N 0.000 claims 1
- LIKKMSJYXQMOCX-UHFFFAOYSA-N 8-[(4-methylpiperidin-4-yl)methoxy]-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound C=1C=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C2C=1OCC1(C)CCNCC1 LIKKMSJYXQMOCX-UHFFFAOYSA-N 0.000 claims 1
- GANFQJFXZYPGOX-UHFFFAOYSA-N 8-[(4-propan-2-ylpiperidin-4-yl)methoxy]-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound C=1C=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C2C=1OCC1(C(C)C)CCNCC1 GANFQJFXZYPGOX-UHFFFAOYSA-N 0.000 claims 1
- YUDHKJJAUQNWBR-NVXWUHKLSA-N 8-[(4r,5r)-5-fluoroazepan-4-yl]oxy-2-(6-fluoro-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound F[C@@H]1CCNCC[C@H]1OC1=CC=CC2=CC=C(C=3N4C=C(F)C=CC4=NN=3)N=C12 YUDHKJJAUQNWBR-NVXWUHKLSA-N 0.000 claims 1
- ORWFEWSJBCTIST-HNNXBMFYSA-N 8-[[(2s)-pyrrolidin-2-yl]methoxy]-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound C=1C=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C2C=1OC[C@@H]1CCCN1 ORWFEWSJBCTIST-HNNXBMFYSA-N 0.000 claims 1
- QJCCGCRBXGFEOI-UHFFFAOYSA-N 8-[[4-(cyclopropylmethyl)piperidin-4-yl]methoxy]-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound C=1C=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C2C=1OCC1(CC2CC2)CCNCC1 QJCCGCRBXGFEOI-UHFFFAOYSA-N 0.000 claims 1
- YUOMNHIIJUOCOA-UHFFFAOYSA-N 8-[[4-fluoro-1-(2-fluoroethyl)piperidin-4-yl]methoxy]-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound C1CN(CCF)CCC1(F)COC1=CC=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C12 YUOMNHIIJUOCOA-UHFFFAOYSA-N 0.000 claims 1
- URCZAWFHBYABKR-UHFFFAOYSA-N 8-piperidin-4-yloxy-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound C1CNCCC1OC1=CC=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C12 URCZAWFHBYABKR-UHFFFAOYSA-N 0.000 claims 1
- LHYMZRAAHMXXAW-UHFFFAOYSA-N 8-pyridin-4-yloxy-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound C=1C=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C2C=1OC1=CC=NC=C1 LHYMZRAAHMXXAW-UHFFFAOYSA-N 0.000 claims 1
- QFYWUMPWXIJTRE-WKILWMFISA-N C1C[C@@H](N)CC[C@@H]1OC1=CC=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C12 Chemical compound C1C[C@@H](N)CC[C@@H]1OC1=CC=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C12 QFYWUMPWXIJTRE-WKILWMFISA-N 0.000 claims 1
- QFYWUMPWXIJTRE-IYBDPMFKSA-N C1C[C@@H](N)CC[C@H]1OC1=CC=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C12 Chemical compound C1C[C@@H](N)CC[C@H]1OC1=CC=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C12 QFYWUMPWXIJTRE-IYBDPMFKSA-N 0.000 claims 1
- UGCCFJQVUHNGIM-WKILWMFISA-N C1C[C@@H](O)CC[C@@H]1NC1=CC=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C12 Chemical compound C1C[C@@H](O)CC[C@@H]1NC1=CC=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C12 UGCCFJQVUHNGIM-WKILWMFISA-N 0.000 claims 1
- JIPAVNODPHBEFL-UHFFFAOYSA-N [1-[[2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]oxymethyl]cyclopentyl]methanamine Chemical compound C=1C=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C2C=1OCC1(CN)CCCC1 JIPAVNODPHBEFL-UHFFFAOYSA-N 0.000 claims 1
- CWRBSZWGCCMVST-UHFFFAOYSA-N [1-[[2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]oxymethyl]cyclopropyl]methanol Chemical compound C=1C=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C2C=1OCC1(CO)CC1 CWRBSZWGCCMVST-UHFFFAOYSA-N 0.000 claims 1
- ANXPRWZUQDZBMG-UHFFFAOYSA-N [3-[8-(2-methylpropoxy)quinolin-2-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]methanamine Chemical compound C1=C(CN)C=CN2C(C3=CC=C4C=CC=C(C4=N3)OCC(C)C)=NN=C21 ANXPRWZUQDZBMG-UHFFFAOYSA-N 0.000 claims 1
- QFVRLYRYKCLRMD-UHFFFAOYSA-N cyclodecane-1,6-diol Chemical compound OC1CCCCC(O)CCCC1 QFVRLYRYKCLRMD-UHFFFAOYSA-N 0.000 claims 1
- YZPCWPMIVKWDOZ-UHFFFAOYSA-N dimethyl 2,2-dioxo-1,3,2-dioxathiolane-4,5-dicarboxylate Chemical compound COC(=O)C1OS(=O)(=O)OC1C(=O)OC YZPCWPMIVKWDOZ-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- JVJPYYIBTFDZRE-UHFFFAOYSA-N n'-(3-methylbutyl)-n'-[2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]propane-1,3-diamine Chemical compound C1=CC=CN2C(C3=CC=C4C=CC=C(C4=N3)N(CCCN)CCC(C)C)=NN=C21 JVJPYYIBTFDZRE-UHFFFAOYSA-N 0.000 claims 1
- HJXCXBOFPAHSQW-UHFFFAOYSA-N n'-[2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]propane-1,3-diamine Chemical compound C1=CC=CN2C(C3=CC=C4C=CC=C(C4=N3)NCCCN)=NN=C21 HJXCXBOFPAHSQW-UHFFFAOYSA-N 0.000 claims 1
- XKKPUVJVSGGFGO-UHFFFAOYSA-N n,2,2-trimethyl-3-[2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]oxypropan-1-amine Chemical compound C1=CC=CN2C(C3=CC=C4C=CC=C(C4=N3)OCC(C)(C)CNC)=NN=C21 XKKPUVJVSGGFGO-UHFFFAOYSA-N 0.000 claims 1
- DWCALHBDVWAIKM-UHFFFAOYSA-N n,n,2,2-tetramethyl-3-[2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]oxypropan-1-amine Chemical compound C1=CC=CN2C(C3=CC=C4C=CC=C(C4=N3)OCC(C)(C)CN(C)C)=NN=C21 DWCALHBDVWAIKM-UHFFFAOYSA-N 0.000 claims 1
- JBHAFDKBLKMXBR-UHFFFAOYSA-N n-(2,2,6,6-tetramethylpiperidin-4-yl)-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)-1h-quinolin-2-amine Chemical compound C1C(C)(C)NC(C)(C)CC1NC1(C=2N3C=CC=CC3=NN=2)C=CC2=CC=CC=C2N1 JBHAFDKBLKMXBR-UHFFFAOYSA-N 0.000 claims 1
- STCFUYVDTGGZPT-UHFFFAOYSA-N n-(2,2-difluoroethyl)-2,2-dimethyl-3-[2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]oxypropan-1-amine Chemical compound C1=CC=CN2C(C3=CC=C4C=CC=C(C4=N3)OCC(C)(CNCC(F)F)C)=NN=C21 STCFUYVDTGGZPT-UHFFFAOYSA-N 0.000 claims 1
- BNRNYCUKAUITIW-CQSZACIVSA-N n-[(3r)-pyrrolidin-3-yl]-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-amine Chemical compound C1NCC[C@H]1NC1=CC=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C12 BNRNYCUKAUITIW-CQSZACIVSA-N 0.000 claims 1
- BNRNYCUKAUITIW-AWEZNQCLSA-N n-[(3s)-pyrrolidin-3-yl]-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-amine Chemical compound C1NCC[C@@H]1NC1=CC=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C12 BNRNYCUKAUITIW-AWEZNQCLSA-N 0.000 claims 1
- CPSNZCXBWOPDKW-UHFFFAOYSA-N n-ethyl-2,2-dimethyl-3-[2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]oxypropan-1-amine Chemical compound C1=CC=CN2C(C3=CC=C4C=CC=C(C4=N3)OCC(C)(C)CNCC)=NN=C21 CPSNZCXBWOPDKW-UHFFFAOYSA-N 0.000 claims 1
- BIOQJVDMPGUPRM-UHFFFAOYSA-N n-piperidin-4-yl-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-amine Chemical compound C1CNCCC1NC1=CC=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C12 BIOQJVDMPGUPRM-UHFFFAOYSA-N 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
- 238000000034 method Methods 0.000 description 4
- 101100297652 Coturnix japonica PIM3 gene Proteins 0.000 description 2
- 108091000080 Phosphotransferase Proteins 0.000 description 2
- 102000020233 phosphotransferase Human genes 0.000 description 2
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- 0 BC(C(*)=C(*)C1CC2)=C(*)C1=N*=C2c1nc(c(O)c(*)c(*)c2*)c2c(*)c1* Chemical compound BC(C(*)=C(*)C1CC2)=C(*)C1=N*=C2c1nc(c(O)c(*)c(*)c2*)c2c(*)c1* 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 102000001253 Protein Kinase Human genes 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037765 diseases and disorders Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 210000002865 immune cell Anatomy 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 108010083755 proto-oncogene proteins pim Proteins 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- OVCXRBARSPBVMC-UHFFFAOYSA-N triazolopyridine Chemical group C=1N2C(C(C)C)=NN=C2C=CC=1C=1OC=NC=1C1=CC=C(F)C=C1 OVCXRBARSPBVMC-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8995208P | 2008-08-19 | 2008-08-19 | |
| US61/089,952 | 2008-08-19 | ||
| US17527709P | 2009-05-04 | 2009-05-04 | |
| US61/175,277 | 2009-05-04 | ||
| PCT/US2009/054193 WO2010022076A1 (en) | 2008-08-19 | 2009-08-18 | Triazolopyridine compounds as pim kinase inhibitors |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014044674A Division JP2014129409A (ja) | 2008-08-19 | 2014-03-07 | Ｐｉｍキナーゼ阻害剤としてのトリアゾロピリジン化合物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012500277A JP2012500277A (ja) | 2012-01-05 |
| JP2012500277A5 true JP2012500277A5 (enExample) | 2012-10-04 |
| JP5518072B2 JP5518072B2 (ja) | 2014-06-11 |
Family
ID=41227138
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011523939A Expired - Fee Related JP5518072B2 (ja) | 2008-08-19 | 2009-08-18 | Ｐｉｍキナーゼ阻害剤としてのトリアゾロピリジン化合物 |
| JP2014044674A Withdrawn JP2014129409A (ja) | 2008-08-19 | 2014-03-07 | Ｐｉｍキナーゼ阻害剤としてのトリアゾロピリジン化合物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014044674A Withdrawn JP2014129409A (ja) | 2008-08-19 | 2014-03-07 | Ｐｉｍキナーゼ阻害剤としてのトリアゾロピリジン化合物 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US8575145B2 (enExample) |
| EP (1) | EP2334677B1 (enExample) |
| JP (2) | JP5518072B2 (enExample) |
| CN (1) | CN102186851B (enExample) |
| AR (1) | AR073079A1 (enExample) |
| CA (1) | CA2734831C (enExample) |
| DK (1) | DK2334677T3 (enExample) |
| ES (1) | ES2439501T3 (enExample) |
| HR (1) | HRP20131140T1 (enExample) |
| PL (1) | PL2334677T3 (enExample) |
| PT (1) | PT2334677E (enExample) |
| RS (1) | RS53079B (enExample) |
| SI (1) | SI2334677T1 (enExample) |
| SM (1) | SMT201400154B (enExample) |
| TW (1) | TWI496779B (enExample) |
| UY (1) | UY32057A (enExample) |
| WO (1) | WO2010022076A1 (enExample) |
Families Citing this family (73)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0420722D0 (en) | 2004-09-17 | 2004-10-20 | Addex Pharmaceuticals Sa | Novel allosteric modulators |
| RS55634B1 (sr) | 2005-12-13 | 2017-06-30 | Incyte Holdings Corp | Heteroaril substituisani pirolo[2,3-b]piridini i pirolo[2,3-b]pirimidini kao inhibitori janus kinaze |
| TWI417095B (zh) | 2006-03-15 | 2013-12-01 | Janssen Pharmaceuticals Inc | １，４-二取代之３-氰基-吡啶酮衍生物及其作為ｍＧｌｕＲ２-受體之正向異位性調節劑之用途 |
| TW200845978A (en) | 2007-03-07 | 2008-12-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-tetrahydropyran-phenyl)-pyridin-2-one derivatives |
| TW200900065A (en) | 2007-03-07 | 2009-01-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-pyridinyloxy-phenyl)-pyridin-2-one derivatives |
| HUE043732T2 (hu) | 2007-06-13 | 2019-09-30 | Incyte Holdings Corp | Januskináz gátló hatású (R)-3-(4-(7H pirrolo[2,3-d]pirimidin-4-il)-1H-pirazol-1-il)-3-ciklopentilpropánnitril sók alkalmazása |
| MX2010002538A (es) | 2007-09-14 | 2010-08-10 | Ortho Mcneil Janssen Pharm | 4-(aril-x-fenil)-1h-piridin-2-onas 1,3-disubstituidas. |
| CA2698929C (en) | 2007-09-14 | 2016-01-19 | Addex Pharma S.A. | 1,3-disubstituted-4-phenyl-1h-pyridin-2-ones |
| MY152078A (en) | 2007-09-14 | 2014-08-15 | Ortho Mcneil Janssen Pharm | 1',3'-disubstituted-4-phenyl-3,4,5,6-tetrahydro-2h,1'h-[1,4']bipyridinyl-2'-ones |
| ES2637794T3 (es) | 2007-11-14 | 2017-10-17 | Janssen Pharmaceuticals, Inc. | Derivados de imidazo[1,2-A]piridina y su uso como moduladores alostéricos positivos de receptores MGLUR2 |
| US8987251B2 (en) | 2008-08-19 | 2015-03-24 | Array Biopharma Inc. | Triazolopyridine compounds as PIM kinase inhibitors |
| AU2009289784B2 (en) | 2008-09-02 | 2012-03-22 | Addex Pharma S.A. | 3-azabicyclo[3.1.0]hexyl derivatives as modulators of metabotropic glutamate receptors |
| RU2517181C2 (ru) | 2008-10-16 | 2014-05-27 | Орто-Макнейл-Янссен Фармасьютикалз, Инк. | Производные индола и бензоморфолина в качестве модулятора метаботропных глутаматных рецепторов |
| CA2744138C (en) | 2008-11-28 | 2015-08-11 | Ortho-Mcneil-Janssen Pharmaceuticals, Inc. | Indole and benzoxazine derivatives as modulators of metabotropic glutamate receptors |
| MY153913A (en) | 2009-05-12 | 2015-04-15 | Janssen Pharmaceuticals Inc | 7-aryl-1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors |
| AU2010246609B2 (en) | 2009-05-12 | 2013-09-05 | Addex Pharma S.A. | 1,2,4-triazolo [4,3-a] pyridine derivatives and their use for the treatment or prevention of neurological and psychiatric disorders |
| EA020671B1 (ru) | 2009-05-12 | 2014-12-30 | Янссен Фармасьютикалз, Инк. | ПРОИЗВОДНЫЕ 1,2,4-ТРИАЗОЛО[4,3-a]ПИРИДИНА И ИХ ПРИМЕНЕНИЕ В КАЧЕСТВЕ ПОЛОЖИТЕЛЬНЫХ АЛЛОСТЕРИЧЕСКИХ МОДУЛЯТОРОВ РЕЦЕПТОРОВ mGluR2 |
| KR20120030447A (ko) | 2009-05-22 | 2012-03-28 | 인사이트 코포레이션 | Ｊａｋ 저해물질로서 ３-［４-（７ｈ-피롤로［２,３-ｄ］피리미딘-４-일）-１ｈ-피라졸-１-일］옥탄- 또는 헵탄-니트릴 |
| EP2432555B1 (en) | 2009-05-22 | 2014-04-30 | Incyte Corporation | N-(hetero)aryl-pyrrolidine derivatives of pyrazol-4-yl-pyrrolo[2,3-d]pyrimidines and pyrrol-3-yl-pyrrolo[2,3-d]pyrimidines as janus kinase inhibitors |
| WO2011028685A1 (en) | 2009-09-01 | 2011-03-10 | Incyte Corporation | Heterocyclic derivatives of pyrazol-4-yl-pyrrolo[2,3-d]pyrimidines as janus kinase inhibitors |
| TWI531572B (zh) | 2010-03-10 | 2016-05-01 | 英塞特公司 | 作為ｊａｋ１抑制劑之哌啶－４－基三亞甲亞胺衍生物 |
| US20110288107A1 (en) | 2010-05-21 | 2011-11-24 | Bhavnish Parikh | Topical formulation for a jak inhibitor |
| CN103298809B (zh) | 2010-11-08 | 2016-08-31 | 杨森制药公司 | 1,2,4-三唑并[4,3-a]吡啶衍生物及其作为MGLUR2受体的正变构调节剂的用途 |
| US9271967B2 (en) | 2010-11-08 | 2016-03-01 | Janssen Pharmaceuticals, Inc. | 1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mGluR2 receptors |
| WO2012062751A1 (en) | 2010-11-08 | 2012-05-18 | Janssen Pharmaceuticals, Inc. | 1,2,4-TRIAZOLO[4,3-a]PYRIDINE DERIVATIVES AND THEIR USE AS POSITIVE ALLOSTERIC MODULATORS OF MGLUR2 RECEPTORS |
| WO2012065297A1 (en) * | 2010-11-16 | 2012-05-24 | Impact Therapeutics, Inc. | 3-ARYL-6-ARYL-[1,2,4]TRIAZOLO[4,3-a]PYRIDINES AS INHIBITORS OF CELL PROLIFERATION AND THE USE THEREOF |
| EP2640725B1 (en) | 2010-11-19 | 2015-01-07 | Incyte Corporation | Heterocyclic-substituted pyrrolopyridines and pyrrolopyrimidines as jak inhibitors |
| PH12013501001A1 (en) | 2010-11-19 | 2019-09-02 | Incyte Holdings Corp | Cyclobutyl substituted pyrrolopyridine and pyrrolopyrimidine derivatives as jak inhibitors |
| WO2012154274A1 (en) * | 2011-02-25 | 2012-11-15 | Array Biopharma Inc. | Triazolopyridine compounds as pim kinase inhibitors |
| AU2012273164B2 (en) | 2011-06-20 | 2015-05-28 | Incyte Holdings Corporation | Azetidinyl phenyl, pyridyl or pyrazinyl carboxamide derivatives as JAK inhibitors |
| WO2013005057A1 (en) | 2011-07-07 | 2013-01-10 | Centro Nacional De Investigaciones Oncológicas (Cnio) | New compounds |
| EP2734205B1 (en) | 2011-07-21 | 2018-03-21 | Tolero Pharmaceuticals, Inc. | Heterocyclic protein kinase inhibitors |
| TW201313721A (zh) | 2011-08-18 | 2013-04-01 | Incyte Corp | 作為ｊａｋ抑制劑之環己基氮雜環丁烷衍生物 |
| UA111854C2 (uk) | 2011-09-07 | 2016-06-24 | Інсайт Холдінгс Корпорейшн | Способи і проміжні сполуки для отримання інгібіторів jak |
| HRP20161714T1 (hr) | 2011-12-09 | 2017-02-10 | Chiesi Farmaceutici S.P.A. | Inhibitori kinaze |
| KR20140103925A (ko) | 2011-12-09 | 2014-08-27 | 키에시 파르마슈티시 엣스. 피. 에이. | 4-히드록시-1,2,3,4-테트라히드로나프탈렌-1-일 우레아 및 호흡기 질환의 치료에서의 이들의 용도 |
| EP2788348B1 (en) | 2011-12-09 | 2016-10-19 | Chiesi Farmaceutici S.p.A. | Kinase inhibitors |
| TW201406761A (zh) | 2012-05-18 | 2014-02-16 | Incyte Corp | 做爲ｊａｋ抑制劑之哌啶基環丁基取代之吡咯并吡啶及吡咯并嘧啶衍生物 |
| CR20190073A (es) | 2012-11-15 | 2019-04-25 | Incyte Holdings Corp | FORMAS DE DOSIFICACIÓN DE RUXOLITINIB DE LIBERACIÓN SOTENIDA (Divisional 2015-265) |
| ES2649156T3 (es) | 2013-01-14 | 2018-01-10 | Incyte Holdings Corporation | Compuestos bicíclicos de carboxamida aromática útiles como inhibidores de quinasas Pim |
| US9200004B2 (en) | 2013-01-15 | 2015-12-01 | Incyte Holdings Corporation | Thiazolecarboxamides and pyridinecarboxamide compounds useful as Pim kinase inhibitors |
| SMT202100694T1 (it) | 2013-03-06 | 2022-03-21 | Incyte Holdings Corp | Procedimenti e intermedi per produrre un inibitore di jak |
| EP2994142A4 (en) * | 2013-05-08 | 2017-03-29 | Colorado Seminary, Which Owns and Operates The University of Denver | Antibiotic and anti-parasitic agents that modulate class ii fructose 1,6-bisphosphate aldolase |
| JO3368B1 (ar) | 2013-06-04 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 6، 7- ثاني هيدرو بيرازولو [5،1-a] بيرازين- 4 (5 يد)- اون واستخدامها بصفة منظمات تفارغية سلبية لمستقبلات ميجلور 2 |
| EP3004097B1 (en) | 2013-06-06 | 2018-01-17 | Chiesi Farmaceutici S.p.A. | Kinase inhibitors |
| CA2920108C (en) | 2013-08-07 | 2022-07-05 | Incyte Corporation | Sustained release dosage forms for a jak1 inhibitor |
| PE20160532A1 (es) | 2013-08-23 | 2016-05-21 | Incyte Corp | Compuesto de carboxamida de furo y tienopiridina utiles como inhibidores de cinasas pim |
| JO3367B1 (ar) | 2013-09-06 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 2،1، 4- ثلاثي زولو [3،4-a] بيريدين واستخدامها بصفة منظمات تفارغية موجبة لمستقبلات ميجلور 2 |
| GB201321742D0 (en) * | 2013-12-09 | 2014-01-22 | Ucb Pharma Sa | Therapeutic agents |
| MX374379B (es) | 2014-01-20 | 2025-03-06 | Cleave Biosciences Inc | PIRIMIDINAS FUSIONADAS QUE TIENEN UN ANILLO HETEROCÍCLICO 5:6 COMO INHIBIDORES DEL COMPLEJO p97 Y EL USO DE LAS MISMAS EN EL TRATAMIENTO DE AFECCIONES NEOPLÁSICAS. |
| WO2015110435A1 (en) | 2014-01-21 | 2015-07-30 | Janssen Pharmaceutica Nv | Combinations comprising positive allosteric modulators or orthosteric agonists of metabotropic glutamatergic receptor subtype 2 and their use |
| HUE045610T2 (hu) | 2014-01-21 | 2020-01-28 | Janssen Pharmaceutica Nv | 2-es altípusú metabotróp glutamáterg receptor pozitív allosztérikus modulátorait vagy ortosztérikus agonistáit tartalmazó kombinációk és alkalmazásuk |
| WO2015184305A1 (en) | 2014-05-30 | 2015-12-03 | Incyte Corporation | TREATMENT OF CHRONIC NEUTROPHILIC LEUKEMIA (CNL) AND ATYPICAL CHRONIC MYELOID LEUKEMIA (aCML) BY INHIBITORS OF JAK1 |
| 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 |
| WO2016196244A1 (en) | 2015-05-29 | 2016-12-08 | Incyte Corporation | Pyridineamine compounds useful as pim kinase inhibitors |
| AR105967A1 (es) | 2015-09-09 | 2017-11-29 | Incyte Corp | Sales de un inhibidor de pim quinasa |
| WO2017059251A1 (en) | 2015-10-02 | 2017-04-06 | Incyte Corporation | Heterocyclic compounds useful as pim kinase inhibitors |
| CN109790166A (zh) | 2016-06-20 | 2019-05-21 | 诺华股份有限公司 | 咪唑并吡啶化合物用于治疗癌症 |
| ES2798424T3 (es) * | 2016-06-20 | 2020-12-11 | Novartis Ag | Compuestos de triazolopiridina y usos de estos |
| ES2975263T3 (es) | 2016-06-20 | 2024-07-04 | Novartis Ag | Formas cristalinas de un compuesto triazolopirimidínico |
| TW201924683A (zh) | 2017-12-08 | 2019-07-01 | 美商英塞特公司 | 用於治療骨髓增生性贅瘤的低劑量組合療法 |
| EP3746429B1 (en) | 2018-01-30 | 2022-03-09 | Incyte Corporation | Processes for preparing (1-(3-fluoro-2-(trifluoromethyl)isonicotinyl)piperidine-4-one) |
| MX2020010322A (es) | 2018-03-30 | 2022-11-30 | Incyte Corp | Tratamiento de la hidradenitis supurativa mediante el uso de inhibidores de actividad de la cinasa janus (jak). |
| AU2019252793A1 (en) | 2018-04-13 | 2020-10-15 | Sumitomo Pharma America, Inc. | PIM kinase inhibitors for treatment of myeloproliferative neoplasms and fibrosis associated with cancer |
| CN113302184B (zh) | 2018-11-15 | 2024-11-22 | 日本新药株式会社 | 1,3,4-噁二唑啉酮化合物和药物 |
| NZ778055A (en) | 2019-02-12 | 2025-11-28 | Sumitomo Pharma America Inc | Formulations comprising heterocyclic protein kinase inhibitors |
| JP7549597B2 (ja) | 2019-03-15 | 2024-09-11 | フルクラム セラピューティクス，インコーポレイテッド | Ｅｅｄおよびｐｒｃ２調節物質としての大環状アゾロピリジン誘導体 |
| CN111138429A (zh) * | 2019-12-31 | 2020-05-12 | 西安邮电大学 | 1,2,4-三氮唑并吡啶类衍生物的合成方法 |
| CN111171023B (zh) * | 2020-01-10 | 2021-12-21 | 中国药科大学 | 一种具有Pim1抑制活性的化合物及其制备方法与医药用途 |
| CN113620942B (zh) * | 2020-05-06 | 2025-02-11 | 北京鼎材科技有限公司 | 一种化合物及其应用 |
| US11833155B2 (en) | 2020-06-03 | 2023-12-05 | Incyte Corporation | Combination therapy for treatment of myeloproliferative neoplasms |
| EP4611753A1 (en) | 2022-10-31 | 2025-09-10 | Sumitomo Pharma America, Inc. | Pim1 inhibitor for treating myeloproliferative neoplasms |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MXPA02004735A (es) | 1999-11-12 | 2003-01-28 | Orive Javier Uhthoff | Compuestos heteroaromaticos, biciclicos y triciclicos. |
| ES2244613T3 (es) | 2000-04-27 | 2005-12-16 | Astellas Pharma Inc. | Derivados de imidazopiridina. |
| DE10038019A1 (de) | 2000-08-04 | 2002-02-14 | Bayer Ag | Substituierte Triazolopyrid(az)ine |
| EE200300437A (et) | 2001-03-09 | 2004-02-16 | Pfizer Products Inc. | Triasolopüridiinid kui põletikuvastased ained |
| US7227006B2 (en) | 2002-01-19 | 2007-06-05 | Sanofi-Aventis Deutschland Gmbh | PIM-3 kinase as a target for type 2 diabetes mellitus |
| WO2004058749A1 (en) | 2002-12-18 | 2004-07-15 | Vertex Pharmaceuticals Incorporated | Benzisoxazole derivatives useful as inhibitors of protein kinases |
| CA2510534C (en) * | 2002-12-18 | 2011-09-20 | Vertex Pharmaceuticals Incorporated | Compositions useful as inhibitors of protein kinases |
| WO2005028624A2 (en) | 2003-09-15 | 2005-03-31 | Plexxikon, Inc. | Molecular scaffolds for kinase ligand development |
| US20050256309A1 (en) * | 2004-05-12 | 2005-11-17 | Altenbach Robert J | Tri-and bi-cyclic heteroaryl histamine-3 receptor ligands |
| US20090215817A1 (en) | 2004-08-18 | 2009-08-27 | Pfizer Inc | Novel Triazolopyridine Compounds for the Treatment of Inflammation |
| AU2005311451A1 (en) | 2004-12-01 | 2006-06-08 | Merck Serono Sa | [1,2,4]triazolo[4,3-a]pyridine derivatives for the treatment of hyperproliferative diseases |
| JP5238506B2 (ja) | 2005-10-06 | 2013-07-17 | エグゼリクシス， インコーポレイテッド | Ｐｉｍ−１および／またはｐｉｍ−３のピリドピリミジノンインヒビター |
| WO2007087250A2 (en) * | 2006-01-23 | 2007-08-02 | Amira Pharmaceuticals, Inc. | Tricyclic inhibitors of 5-lipoxygenase |
| CN101516883A (zh) | 2006-06-06 | 2009-08-26 | 先灵公司 | 作为蛋白激酶抑制剂的咪唑并吡嗪化合物 |
| EP2061762B1 (en) * | 2006-08-16 | 2011-07-27 | Boehringer Ingelheim International GmbH | Pyrazine compounds, their use and methods of preparation |
| EP2086979B1 (en) | 2006-11-06 | 2015-06-03 | Tolero Pharmaceuticals, Inc. | Imidazo[1,2-b]pyridazine and pyrazolo[1,5-a]pyrimidine derivatives and their use as protein kinase inhibitors |
| WO2008082839A2 (en) | 2006-12-29 | 2008-07-10 | Abbott Laboratories | Pim kinase inhibitors as cancer chemotherapeutics |
| CN101679422A (zh) * | 2007-03-28 | 2010-03-24 | 阵列生物制药公司 | 作为受体酪氨酸激酶抑制剂的咪唑并[1,2-a]吡啶化合物 |
-
2009
- 2009-08-14 TW TW098127485A patent/TWI496779B/zh not_active IP Right Cessation
- 2009-08-18 UY UY0001032057A patent/UY32057A/es active IP Right Grant
- 2009-08-18 PL PL09791625T patent/PL2334677T3/pl unknown
- 2009-08-18 EP EP09791625.8A patent/EP2334677B1/en active Active
- 2009-08-18 HR HRP20131140AT patent/HRP20131140T1/hr unknown
- 2009-08-18 WO PCT/US2009/054193 patent/WO2010022076A1/en not_active Ceased
- 2009-08-18 SI SI200930782T patent/SI2334677T1/sl unknown
- 2009-08-18 RS RS20130557A patent/RS53079B/sr unknown
- 2009-08-18 DK DK09791625.8T patent/DK2334677T3/da active
- 2009-08-18 ES ES09791625.8T patent/ES2439501T3/es active Active
- 2009-08-18 CN CN2009801413028A patent/CN102186851B/zh not_active Expired - Fee Related
- 2009-08-18 JP JP2011523939A patent/JP5518072B2/ja not_active Expired - Fee Related
- 2009-08-18 AR ARP090103170A patent/AR073079A1/es active IP Right Grant
- 2009-08-18 PT PT97916258T patent/PT2334677E/pt unknown
- 2009-08-18 US US13/059,902 patent/US8575145B2/en not_active Expired - Fee Related
- 2009-08-18 CA CA2734831A patent/CA2734831C/en not_active Expired - Fee Related
-
2014
- 2014-03-07 JP JP2014044674A patent/JP2014129409A/ja not_active Withdrawn
- 2014-10-21 SM SM201400154T patent/SMT201400154B/xx unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2012500277A5 (enExample) | ||
| JP5518072B2 (ja) | Ｐｉｍキナーゼ阻害剤としてのトリアゾロピリジン化合物 | |
| JP2010523576A5 (enExample) | ||
| KR101940338B1 (ko) | Pim 키나제 억제제로서의 트라이아졸로피리딘 화합물 | |
| RU2467008C2 (ru) | СОЕДИНЕНИЯ ИМИДАЗО[1,2-a]ПИРИДИНА В КАЧЕСТВЕ ИНГИБИТОРОВ РЕЦЕПТОРНЫХ ТИРОЗИНКИНАЗ | |
| US9694006B2 (en) | Use of pyrroloquinoline compounds to kill clinically latent microorganisms | |
| US9815832B2 (en) | Azabenzimidazole compounds | |
| KR100777885B1 (ko) | Ｈｉｖ 및 염증 치료를 위한 ｃｃｒ5 수용체 길항제 활성을갖는 이미다조피리딘 치환된 트로판 유도체 | |
| JP2014511893A5 (enExample) | ||
| RU2016110483A (ru) | Производные пирролопиридина или пиразолопиридина | |
| NZ728122A (en) | 6,7-dihydropyrazolo[1,5-a]pyrazin-4(5h)-one compounds and their use as negative allosteric modulators of mglur2 receptors | |
| TW202529806A (zh) | 包含ｋｒａｓ ｇ１２ｄ抑制劑及ｅｇｆｒ抑制劑之組合療法 | |
| JP2011522849A5 (enExample) | ||
| JP2008533082A5 (enExample) | ||
| US8987251B2 (en) | Triazolopyridine compounds as PIM kinase inhibitors | |
| JPWO2023091746A5 (enExample) |