JP2016525509A5 - - Google Patents
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- JP2016525509A5 JP2016525509A5 JP2016524675A JP2016524675A JP2016525509A5 JP 2016525509 A5 JP2016525509 A5 JP 2016525509A5 JP 2016524675 A JP2016524675 A JP 2016524675A JP 2016524675 A JP2016524675 A JP 2016524675A JP 2016525509 A5 JP2016525509 A5 JP 2016525509A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrimidin
- chloro
- phenyl
- ylamino
- dimethylamino
- 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 —O-heterocycle Chemical group 0.000 claims 45
- 150000001875 compounds Chemical class 0.000 claims 28
- 125000000217 alkyl group Chemical group 0.000 claims 27
- 125000000623 heterocyclic group Chemical group 0.000 claims 20
- 229910052736 halogen Inorganic materials 0.000 claims 19
- 150000002367 halogens Chemical group 0.000 claims 19
- 125000003545 alkoxy group Chemical group 0.000 claims 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims 11
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims 8
- 206010028980 Neoplasm Diseases 0.000 claims 8
- 125000003342 alkenyl group Chemical group 0.000 claims 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 8
- 201000011510 cancer Diseases 0.000 claims 7
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 6
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 6
- 102000052116 epidermal growth factor receptor activity proteins Human genes 0.000 claims 6
- 108700015053 epidermal growth factor receptor activity proteins Proteins 0.000 claims 6
- 125000004404 heteroalkyl group Chemical group 0.000 claims 6
- YOHYSYJDKVYCJI-UHFFFAOYSA-N n-[3-[[6-[3-(trifluoromethyl)anilino]pyrimidin-4-yl]amino]phenyl]cyclopropanecarboxamide Chemical compound FC(F)(F)C1=CC=CC(NC=2N=CN=C(NC=3C=C(NC(=O)C4CC4)C=CC=3)C=2)=C1 YOHYSYJDKVYCJI-UHFFFAOYSA-N 0.000 claims 6
- 125000001188 haloalkyl group Chemical group 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 125000005842 heteroatom Chemical group 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 4
- 102100033793 ALK tyrosine kinase receptor Human genes 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- KTONNTOWXWZRTD-UHFFFAOYSA-N 2-[2-[[5-chloro-2-[4-[4-(dimethylamino)piperidin-1-yl]-2-methoxyanilino]pyrimidin-4-yl]amino]phenyl]-2-oxoacetic acid Chemical compound COC1=CC(N2CCC(CC2)N(C)C)=CC=C1NC(N=1)=NC=C(Cl)C=1NC1=CC=CC=C1C(=O)C(O)=O KTONNTOWXWZRTD-UHFFFAOYSA-N 0.000 claims 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 206010027476 Metastases Diseases 0.000 claims 2
- 108091000080 Phosphotransferase Proteins 0.000 claims 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 208000030533 eye disease Diseases 0.000 claims 2
- 108020001507 fusion proteins Proteins 0.000 claims 2
- 102000037865 fusion proteins Human genes 0.000 claims 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 2
- 208000026278 immune system disease Diseases 0.000 claims 2
- 230000009401 metastasis Effects 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 102000020233 phosphotransferase Human genes 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- ILLYKAKXONHJRD-RMKNXTFCSA-N (e)-n-[3-[[5-chloro-4-[2-[2-(dimethylamino)-2-oxoacetyl]anilino]pyrimidin-2-yl]amino]-4-methoxyphenyl]-4-morpholin-4-ylbut-2-enamide Chemical compound C1=C(NC=2N=C(NC=3C(=CC=CC=3)C(=O)C(=O)N(C)C)C(Cl)=CN=2)C(OC)=CC=C1NC(=O)\C=C\CN1CCOCC1 ILLYKAKXONHJRD-RMKNXTFCSA-N 0.000 claims 1
- RWVBCVGNYVHDIE-VMPITWQZSA-N (e)-n-[3-[[5-chloro-4-[2-[2-(dimethylamino)-2-oxoacetyl]anilino]pyrimidin-2-yl]amino]-4-methoxyphenyl]but-2-enamide Chemical compound COC1=CC=C(NC(=O)\C=C\C)C=C1NC1=NC=C(Cl)C(NC=2C(=CC=CC=2)C(=O)C(=O)N(C)C)=N1 RWVBCVGNYVHDIE-VMPITWQZSA-N 0.000 claims 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims 1
- FRRCZEINUNMNNX-UHFFFAOYSA-N 1-[2-[[2-[2-methoxy-4-(4-methylpiperazin-1-yl)anilino]-5-(trifluoromethyl)pyrimidin-4-yl]amino]phenyl]-2-morpholin-4-ylethane-1,2-dione Chemical compound COC1=CC(N2CCN(C)CC2)=CC=C1NC(N=1)=NC=C(C(F)(F)F)C=1NC1=CC=CC=C1C(=O)C(=O)N1CCOCC1 FRRCZEINUNMNNX-UHFFFAOYSA-N 0.000 claims 1
- HGXZFEHOKFOTQQ-UHFFFAOYSA-N 1-[2-[[2-[4-(4-acetylpiperazin-1-yl)-2-methoxyanilino]-5-chloropyrimidin-4-yl]amino]phenyl]-2-morpholin-4-ylethane-1,2-dione Chemical compound COC1=CC(N2CCN(CC2)C(C)=O)=CC=C1NC(N=1)=NC=C(Cl)C=1NC1=CC=CC=C1C(=O)C(=O)N1CCOCC1 HGXZFEHOKFOTQQ-UHFFFAOYSA-N 0.000 claims 1
- OOURWTXSGRFQDW-UHFFFAOYSA-N 1-[2-[[2-[4-[4-(dimethylamino)piperidin-1-yl]-2-methoxyanilino]-5-(trifluoromethyl)pyrimidin-4-yl]amino]phenyl]-2-morpholin-4-ylethane-1,2-dione Chemical compound COC1=CC(N2CCC(CC2)N(C)C)=CC=C1NC(N=1)=NC=C(C(F)(F)F)C=1NC1=CC=CC=C1C(=O)C(=O)N1CCOCC1 OOURWTXSGRFQDW-UHFFFAOYSA-N 0.000 claims 1
- MMCUGRPNLUIXRH-UHFFFAOYSA-N 1-[2-[[5-chloro-2-[2-methoxy-4-(4-methylpiperazin-1-yl)anilino]pyrimidin-4-yl]amino]phenyl]-2-morpholin-4-ylethane-1,2-dione Chemical compound COC1=CC(N2CCN(C)CC2)=CC=C1NC(N=1)=NC=C(Cl)C=1NC1=CC=CC=C1C(=O)C(=O)N1CCOCC1 MMCUGRPNLUIXRH-UHFFFAOYSA-N 0.000 claims 1
- HNWQYLKLVZFIOM-UHFFFAOYSA-N 1-[2-[[5-chloro-2-[4-[4-(dimethylamino)piperidin-1-yl]-2-methoxyanilino]pyrimidin-4-yl]amino]phenyl]-2-morpholin-4-ylethane-1,2-dione Chemical compound COC1=CC(N2CCC(CC2)N(C)C)=CC=C1NC(N=1)=NC=C(Cl)C=1NC1=CC=CC=C1C(=O)C(=O)N1CCOCC1 HNWQYLKLVZFIOM-UHFFFAOYSA-N 0.000 claims 1
- MHBWCASJSCTIPX-UHFFFAOYSA-N 1-[2-[[5-chloro-2-[4-[4-(dimethylamino)piperidin-1-yl]-2-methoxyanilino]pyrimidin-4-yl]amino]phenyl]-3-(dimethylamino)propane-1,2-dione Chemical compound COC1=CC(N2CCC(CC2)N(C)C)=CC=C1NC(N=1)=NC=C(Cl)C=1NC1=CC=CC=C1C(=O)C(=O)CN(C)C MHBWCASJSCTIPX-UHFFFAOYSA-N 0.000 claims 1
- SVXOOWAZKQYAKQ-UHFFFAOYSA-N 1-[2-[[5-chloro-2-[4-[4-(dimethylamino)piperidin-1-yl]-2-methoxyanilino]pyrimidin-4-yl]amino]phenyl]-3-methylbutane-1,2-dione Chemical compound COC1=CC(N2CCC(CC2)N(C)C)=CC=C1NC(N=1)=NC=C(Cl)C=1NC1=CC=CC=C1C(=O)C(=O)C(C)C SVXOOWAZKQYAKQ-UHFFFAOYSA-N 0.000 claims 1
- XYNIINMLCORQHR-UHFFFAOYSA-N 1-[2-[[5-chloro-2-[4-[4-(dimethylamino)piperidin-1-yl]-2-methoxyanilino]pyrimidin-4-yl]amino]phenyl]propane-1,2-dione Chemical compound COC1=CC(N2CCC(CC2)N(C)C)=CC=C1NC(N=1)=NC=C(Cl)C=1NC1=CC=CC=C1C(=O)C(C)=O XYNIINMLCORQHR-UHFFFAOYSA-N 0.000 claims 1
- CEVCZHWHGPPYAQ-UHFFFAOYSA-N 2-[2-[[2-(5-methyl-4-piperidin-4-yl-2-propan-2-yloxyanilino)-5-(trifluoromethyl)pyrimidin-4-yl]amino]phenyl]-2-oxoacetamide Chemical compound CC=1C=C(NC=2N=C(NC=3C(=CC=CC=3)C(=O)C(N)=O)C(=CN=2)C(F)(F)F)C(OC(C)C)=CC=1C1CCNCC1 CEVCZHWHGPPYAQ-UHFFFAOYSA-N 0.000 claims 1
- XOOXHSGUXZVMHW-UHFFFAOYSA-N 2-[2-[[2-[2-methoxy-4-(4-methylpiperazin-1-yl)anilino]-5-(trifluoromethyl)pyrimidin-4-yl]amino]phenyl]-2-oxoacetamide Chemical compound COC1=CC(N2CCN(C)CC2)=CC=C1NC(N=1)=NC=C(C(F)(F)F)C=1NC1=CC=CC=C1C(=O)C(N)=O XOOXHSGUXZVMHW-UHFFFAOYSA-N 0.000 claims 1
- VAZJPWRFIIAFOG-UHFFFAOYSA-N 2-[2-[[2-[4-(4-acetylpiperazin-1-yl)-2-methoxyanilino]-5-chloropyrimidin-4-yl]amino]phenyl]-2-oxoacetamide Chemical compound COC1=CC(N2CCN(CC2)C(C)=O)=CC=C1NC(N=1)=NC=C(Cl)C=1NC1=CC=CC=C1C(=O)C(N)=O VAZJPWRFIIAFOG-UHFFFAOYSA-N 0.000 claims 1
- RKRWLTRLAVJFEK-UHFFFAOYSA-N 2-[2-[[2-[4-(4-acetylpiperazin-1-yl)-2-methoxyanilino]-5-chloropyrimidin-4-yl]amino]phenyl]-n-cyclopropyl-2-oxoacetamide Chemical compound COC1=CC(N2CCN(CC2)C(C)=O)=CC=C1NC(N=1)=NC=C(Cl)C=1NC1=CC=CC=C1C(=O)C(=O)NC1CC1 RKRWLTRLAVJFEK-UHFFFAOYSA-N 0.000 claims 1
- OPGVLJXVFJLLDZ-UHFFFAOYSA-N 2-[2-[[2-[4-[4-(dimethylamino)piperidin-1-yl]-2-methoxyanilino]-5-(trifluoromethyl)pyrimidin-4-yl]amino]phenyl]-2-oxoacetic acid Chemical compound COC1=CC(N2CCC(CC2)N(C)C)=CC=C1NC(N=1)=NC=C(C(F)(F)F)C=1NC1=CC=CC=C1C(=O)C(O)=O OPGVLJXVFJLLDZ-UHFFFAOYSA-N 0.000 claims 1
- LAQSBYOOKAWFSV-UHFFFAOYSA-N 2-[2-[[2-[4-[[1-(2-fluoroethyl)azetidin-3-yl]amino]-2-methoxyanilino]-5-(trifluoromethyl)pyrimidin-4-yl]amino]phenyl]-2-oxoacetamide Chemical compound C=1C=C(NC=2N=C(NC=3C(=CC=CC=3)C(=O)C(N)=O)C(=CN=2)C(F)(F)F)C(OC)=CC=1NC1CN(CCF)C1 LAQSBYOOKAWFSV-UHFFFAOYSA-N 0.000 claims 1
- AERYPYJUMMERSC-UHFFFAOYSA-N 2-[2-[[5-chloro-2-(2-methoxy-4-morpholin-4-ylanilino)pyrimidin-4-yl]amino]phenyl]-n,n-dimethyl-2-oxoacetamide Chemical compound COC1=CC(N2CCOCC2)=CC=C1NC(N=1)=NC=C(Cl)C=1NC1=CC=CC=C1C(=O)C(=O)N(C)C AERYPYJUMMERSC-UHFFFAOYSA-N 0.000 claims 1
- RSIQSLXNWUEYCL-UHFFFAOYSA-N 2-[2-[[5-chloro-2-(2-methoxy-4-morpholin-4-ylanilino)pyrimidin-4-yl]amino]phenyl]-n-cyclopropyl-2-oxoacetamide Chemical compound COC1=CC(N2CCOCC2)=CC=C1NC(N=1)=NC=C(Cl)C=1NC1=CC=CC=C1C(=O)C(=O)NC1CC1 RSIQSLXNWUEYCL-UHFFFAOYSA-N 0.000 claims 1
- YPHMDPDDBHBKPH-UHFFFAOYSA-N 2-[2-[[5-chloro-2-(2-methoxy-4-piperidin-4-ylanilino)pyrimidin-4-yl]amino]phenyl]prop-2-enoic acid Chemical compound COC1=CC(C2CCNCC2)=CC=C1NC(N=1)=NC=C(Cl)C=1NC1=CC=CC=C1C(=C)C(O)=O YPHMDPDDBHBKPH-UHFFFAOYSA-N 0.000 claims 1
- NUMIRKOBHLNKEQ-UHFFFAOYSA-N 2-[2-[[5-chloro-2-(4-fluoro-3-methoxyanilino)pyrimidin-4-yl]amino]phenyl]-2-oxo-n-(1-prop-2-enoylpiperidin-4-yl)acetamide Chemical compound C1=C(F)C(OC)=CC(NC=2N=C(NC=3C(=CC=CC=3)C(=O)C(=O)NC3CCN(CC3)C(=O)C=C)C(Cl)=CN=2)=C1 NUMIRKOBHLNKEQ-UHFFFAOYSA-N 0.000 claims 1
- CUOFJQAAYKJYJM-UHFFFAOYSA-N 2-[2-[[5-chloro-2-(4-fluoro-3-methoxyanilino)pyrimidin-4-yl]amino]phenyl]-n,n-dimethyl-2-oxoacetamide Chemical compound C1=C(F)C(OC)=CC(NC=2N=C(NC=3C(=CC=CC=3)C(=O)C(=O)N(C)C)C(Cl)=CN=2)=C1 CUOFJQAAYKJYJM-UHFFFAOYSA-N 0.000 claims 1
- FWPFRLAKYIVTFY-UHFFFAOYSA-N 2-[2-[[5-chloro-2-(4-fluoro-3-methoxyanilino)pyrimidin-4-yl]amino]phenyl]-n-methyl-2-oxoacetamide Chemical compound CNC(=O)C(=O)C1=CC=CC=C1NC1=NC(NC=2C=C(OC)C(F)=CC=2)=NC=C1Cl FWPFRLAKYIVTFY-UHFFFAOYSA-N 0.000 claims 1
- DCYQQOSGSUVQOP-UHFFFAOYSA-N 2-[2-[[5-chloro-2-(5-methyl-4-piperidin-4-yl-2-propan-2-yloxyanilino)pyrimidin-4-yl]amino]phenyl]-2-oxoacetamide Chemical compound CC=1C=C(NC=2N=C(NC=3C(=CC=CC=3)C(=O)C(N)=O)C(Cl)=CN=2)C(OC(C)C)=CC=1C1CCNCC1 DCYQQOSGSUVQOP-UHFFFAOYSA-N 0.000 claims 1
- MVLGFIGPCZYXSX-UHFFFAOYSA-N 2-[2-[[5-chloro-2-[2-methoxy-4-(1-methylpiperidin-4-yl)anilino]pyrimidin-4-yl]amino]phenyl]prop-2-enoic acid Chemical compound COC1=CC(C2CCN(C)CC2)=CC=C1NC(N=1)=NC=C(Cl)C=1NC1=CC=CC=C1C(=C)C(O)=O MVLGFIGPCZYXSX-UHFFFAOYSA-N 0.000 claims 1
- JLWCHILGPBXURH-UHFFFAOYSA-N 2-[2-[[5-chloro-2-[2-methoxy-4-(4-methylpiperazin-1-yl)anilino]pyrimidin-4-yl]amino]phenyl]-2-oxo-n-(1-prop-2-enoylazetidin-3-yl)acetamide Chemical compound COC1=CC(N2CCN(C)CC2)=CC=C1NC(N=1)=NC=C(Cl)C=1NC1=CC=CC=C1C(=O)C(=O)NC1CN(C(=O)C=C)C1 JLWCHILGPBXURH-UHFFFAOYSA-N 0.000 claims 1
- NGVDIADNZJLPMD-UHFFFAOYSA-N 2-[2-[[5-chloro-2-[2-methoxy-4-(4-methylpiperazin-1-yl)anilino]pyrimidin-4-yl]amino]phenyl]-2-oxoacetamide Chemical compound COC1=CC(N2CCN(C)CC2)=CC=C1NC(N=1)=NC=C(Cl)C=1NC1=CC=CC=C1C(=O)C(N)=O NGVDIADNZJLPMD-UHFFFAOYSA-N 0.000 claims 1
- XINCMWVRVWORPO-UHFFFAOYSA-N 2-[2-[[5-chloro-2-[2-methoxy-4-(4-methylpiperazin-1-yl)anilino]pyrimidin-4-yl]amino]phenyl]-n-cyclopropyl-2-oxoacetamide Chemical compound COC1=CC(N2CCN(C)CC2)=CC=C1NC(N=1)=NC=C(Cl)C=1NC1=CC=CC=C1C(=O)C(=O)NC1CC1 XINCMWVRVWORPO-UHFFFAOYSA-N 0.000 claims 1
- WMJNZVCMRZGYMH-UHFFFAOYSA-N 2-[2-[[5-chloro-2-[2-methoxy-4-(4-methylpiperazin-1-yl)anilino]pyrimidin-4-yl]amino]phenyl]-n-methyl-2-oxoacetamide Chemical compound CNC(=O)C(=O)C1=CC=CC=C1NC1=NC(NC=2C(=CC(=CC=2)N2CCN(C)CC2)OC)=NC=C1Cl WMJNZVCMRZGYMH-UHFFFAOYSA-N 0.000 claims 1
- XACHZVJBZTVCPK-UHFFFAOYSA-N 2-[2-[[5-chloro-2-[2-methoxy-4-(4-methylpiperazin-1-yl)anilino]pyrimidin-4-yl]amino]phenyl]prop-2-enoic acid Chemical compound COC1=CC(N2CCN(C)CC2)=CC=C1NC(N=1)=NC=C(Cl)C=1NC1=CC=CC=C1C(=C)C(O)=O XACHZVJBZTVCPK-UHFFFAOYSA-N 0.000 claims 1
- ACUPPRKZIQHZNP-UHFFFAOYSA-N 2-[2-[[5-chloro-2-[2-methoxy-4-(4-propanoylpiperazin-1-yl)anilino]pyrimidin-4-yl]amino]phenyl]-n-methyl-2-oxoacetamide Chemical compound C1CN(C(=O)CC)CCN1C(C=C1OC)=CC=C1NC1=NC=C(Cl)C(NC=2C(=CC=CC=2)C(=O)C(=O)NC)=N1 ACUPPRKZIQHZNP-UHFFFAOYSA-N 0.000 claims 1
- BJFDBMNLCPJVHU-UHFFFAOYSA-N 2-[2-[[5-chloro-2-[2-methoxy-4-[4-(methylamino)piperidin-1-yl]anilino]pyrimidin-4-yl]amino]phenyl]-n-(2-hydroxyethyl)-2-oxoacetamide Chemical compound C1CC(NC)CCN1C(C=C1OC)=CC=C1NC1=NC=C(Cl)C(NC=2C(=CC=CC=2)C(=O)C(=O)NCCO)=N1 BJFDBMNLCPJVHU-UHFFFAOYSA-N 0.000 claims 1
- DIQHRPNVYBPCQW-UHFFFAOYSA-N 2-[2-[[5-chloro-2-[3-methoxy-4-(4-methylpiperazin-1-yl)anilino]pyrimidin-4-yl]amino]phenyl]-n,n-dimethyl-2-oxoacetamide Chemical compound C=1C=C(N2CCN(C)CC2)C(OC)=CC=1NC(N=1)=NC=C(Cl)C=1NC1=CC=CC=C1C(=O)C(=O)N(C)C DIQHRPNVYBPCQW-UHFFFAOYSA-N 0.000 claims 1
- UBPDOQYPGGLAJG-UHFFFAOYSA-N 2-[2-[[5-chloro-2-[3-methoxy-4-(4-methylpiperazin-1-yl)anilino]pyrimidin-4-yl]amino]phenyl]-n-methyl-2-oxoacetamide Chemical compound CNC(=O)C(=O)C1=CC=CC=C1NC1=NC(NC=2C=C(OC)C(N3CCN(C)CC3)=CC=2)=NC=C1Cl UBPDOQYPGGLAJG-UHFFFAOYSA-N 0.000 claims 1
- AMSONZZHZCNUHV-UHFFFAOYSA-N 2-[2-[[5-chloro-2-[4-[4-(dimethylamino)piperidin-1-yl]-2-methoxyanilino]pyrimidin-4-yl]amino]phenyl]-2-oxoacetamide Chemical compound COC1=CC(N2CCC(CC2)N(C)C)=CC=C1NC(N=1)=NC=C(Cl)C=1NC1=CC=CC=C1C(=O)C(N)=O AMSONZZHZCNUHV-UHFFFAOYSA-N 0.000 claims 1
- MYIWVWKTSMMMKQ-UHFFFAOYSA-N 2-[2-[[5-chloro-2-[4-[4-(dimethylamino)piperidin-1-yl]-2-methoxyanilino]pyrimidin-4-yl]amino]phenyl]-n,n-dimethyl-2-oxoacetamide Chemical compound COC1=CC(N2CCC(CC2)N(C)C)=CC=C1NC(N=1)=NC=C(Cl)C=1NC1=CC=CC=C1C(=O)C(=O)N(C)C MYIWVWKTSMMMKQ-UHFFFAOYSA-N 0.000 claims 1
- CPYWRIFWULRBFC-UHFFFAOYSA-N 2-[2-[[5-chloro-2-[4-[4-(dimethylamino)piperidin-1-yl]-2-methoxyanilino]pyrimidin-4-yl]amino]phenyl]-n-cyclopropyl-2-oxoacetamide Chemical compound COC1=CC(N2CCC(CC2)N(C)C)=CC=C1NC(N=1)=NC=C(Cl)C=1NC1=CC=CC=C1C(=O)C(=O)NC1CC1 CPYWRIFWULRBFC-UHFFFAOYSA-N 0.000 claims 1
- JLFPEHXJEYWJFT-UHFFFAOYSA-N 2-[2-[[5-chloro-2-[4-[4-(dimethylamino)piperidin-1-yl]-2-methoxyanilino]pyrimidin-4-yl]amino]phenyl]-n-hydroxy-2-oxoacetamide Chemical compound COC1=CC(N2CCC(CC2)N(C)C)=CC=C1NC(N=1)=NC=C(Cl)C=1NC1=CC=CC=C1C(=O)C(=O)NO JLFPEHXJEYWJFT-UHFFFAOYSA-N 0.000 claims 1
- NIRIQZRPPUKCOA-UHFFFAOYSA-N 2-[2-[[5-chloro-2-[4-[4-(dimethylamino)piperidin-1-yl]-2-methoxyanilino]pyrimidin-4-yl]amino]phenyl]-n-methyl-2-oxoacetamide Chemical compound CNC(=O)C(=O)C1=CC=CC=C1NC1=NC(NC=2C(=CC(=CC=2)N2CCC(CC2)N(C)C)OC)=NC=C1Cl NIRIQZRPPUKCOA-UHFFFAOYSA-N 0.000 claims 1
- YAJAQZIBHSVGQC-UHFFFAOYSA-N 2-[2-[[5-chloro-2-[4-[[1-(2-fluoroethyl)azetidin-3-yl]amino]-2-methoxyanilino]pyrimidin-4-yl]amino]phenyl]-2-oxoacetamide Chemical compound C=1C=C(NC=2N=C(NC=3C(=CC=CC=3)C(=O)C(N)=O)C(Cl)=CN=2)C(OC)=CC=1NC1CN(CCF)C1 YAJAQZIBHSVGQC-UHFFFAOYSA-N 0.000 claims 1
- PHGJBYINNNRCCL-UHFFFAOYSA-N 2-[2-[[5-chloro-2-[4-[[1-(2-fluoroethyl)azetidin-3-yl]amino]-2-methoxyanilino]pyrimidin-4-yl]amino]phenyl]prop-2-enoic acid Chemical compound C=1C=C(NC=2N=C(NC=3C(=CC=CC=3)C(=C)C(O)=O)C(Cl)=CN=2)C(OC)=CC=1NC1CN(CCF)C1 PHGJBYINNNRCCL-UHFFFAOYSA-N 0.000 claims 1
- 125000001627 3 membered heterocyclic group Chemical group 0.000 claims 1
- 125000001963 4 membered heterocyclic group Chemical group 0.000 claims 1
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 1
- 101710168331 ALK tyrosine kinase receptor Proteins 0.000 claims 1
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| CN102264736B (zh) | 2008-10-22 | 2013-08-14 | 阵列生物制药公司 | 作为TRK激酶抑制剂的取代的吡唑并[1,5-a]嘧啶化合物 |
| AR077468A1 (es) | 2009-07-09 | 2011-08-31 | Array Biopharma Inc | Compuestos de pirazolo (1,5 -a) pirimidina sustituidos como inhibidores de trk- quinasa |
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| US7989465B2 (en) * | 2007-10-19 | 2011-08-02 | Avila Therapeutics, Inc. | 4,6-disubstituted pyrimidines useful as kinase inhibitors |
| US8338439B2 (en) * | 2008-06-27 | 2012-12-25 | Celgene Avilomics Research, Inc. | 2,4-disubstituted pyrimidines useful as kinase inhibitors |
| AU2009262068C1 (en) * | 2008-06-27 | 2015-07-02 | Celgene Car Llc | Heteroaryl compounds and uses thereof |
| TW201024281A (en) | 2008-11-24 | 2010-07-01 | Boehringer Ingelheim Int | New compounds |
| WO2011140338A1 (en) * | 2010-05-05 | 2011-11-10 | Gatekeeper Pharmaceuticals, Inc. | Compounds that modulate egfr activity and methods for treating or preventing conditions therewith |
| PT2670401E (pt) * | 2011-02-02 | 2015-10-12 | Novartis Ag | Métodos de utilização de inibidores de alk |
-
2014
- 2014-07-11 JP JP2016524675A patent/JP6510510B2/ja not_active Expired - Fee Related
- 2014-07-11 RU RU2016103938A patent/RU2656591C2/ru active
- 2014-07-11 TW TW103124057A patent/TWI610923B/zh not_active IP Right Cessation
- 2014-07-11 CN CN201480039578.6A patent/CN105377835B/zh not_active Expired - Fee Related
- 2014-07-11 CA CA2917735A patent/CA2917735C/en not_active Expired - Fee Related
- 2014-07-11 SG SG11201600055PA patent/SG11201600055PA/en unknown
- 2014-07-11 US US14/903,369 patent/US9783524B2/en not_active Expired - Fee Related
- 2014-07-11 WO PCT/CN2014/082084 patent/WO2015003658A1/en not_active Ceased
- 2014-07-11 EP EP14822363.9A patent/EP3019489A4/en not_active Withdrawn
- 2014-07-11 AU AU2014289762A patent/AU2014289762B2/en not_active Ceased
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2017
- 2017-09-01 US US15/694,620 patent/US10059688B2/en not_active Expired - Fee Related
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