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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- FGVHSXSFGJBPAC-UHFFFAOYSA-N n-[3-[[5-chloro-4-[2-[2-[2-(dimethylamino)ethylamino]-2-oxoacetyl]anilino]pyrimidin-2-yl]amino]phenyl]prop-2-enamide Chemical compound CN(C)CCNC(=O)C(=O)C1=CC=CC=C1NC1=NC(NC=2C=C(NC(=O)C=C)C=CC=2)=NC=C1Cl FGVHSXSFGJBPAC-UHFFFAOYSA-N 0.000 claims 1
- LMGLKFHIVGJIEB-UHFFFAOYSA-N n-[5-[[5-chloro-4-[2-(2-morpholin-4-yl-2-oxoacetyl)anilino]pyrimidin-2-yl]amino]-2-methoxyphenyl]prop-2-enamide Chemical compound C1=C(NC(=O)C=C)C(OC)=CC=C1NC1=NC=C(Cl)C(NC=2C(=CC=CC=2)C(=O)C(=O)N2CCOCC2)=N1 LMGLKFHIVGJIEB-UHFFFAOYSA-N 0.000 claims 1
- UOUZXAIBJBCTIX-UHFFFAOYSA-N n-[5-[[5-chloro-4-[2-[2-(4-methylpiperazin-1-yl)-2-oxoacetyl]anilino]pyrimidin-2-yl]amino]-2-methoxyphenyl]prop-2-enamide Chemical compound C1=C(NC(=O)C=C)C(OC)=CC=C1NC1=NC=C(Cl)C(NC=2C(=CC=CC=2)C(=O)C(=O)N2CCN(C)CC2)=N1 UOUZXAIBJBCTIX-UHFFFAOYSA-N 0.000 claims 1
- BQGJJCRERBDMEC-UHFFFAOYSA-N n-[5-[[5-chloro-4-[2-[2-(dimethylamino)-2-oxoacetyl]anilino]pyrimidin-2-yl]amino]-2-[2-(dimethylamino)ethoxy]phenyl]-3-methoxypropanamide Chemical compound C1=C(OCCN(C)C)C(NC(=O)CCOC)=CC(NC=2N=C(NC=3C(=CC=CC=3)C(=O)C(=O)N(C)C)C(Cl)=CN=2)=C1 BQGJJCRERBDMEC-UHFFFAOYSA-N 0.000 claims 1
- YLORQIIPEBGMJH-UHFFFAOYSA-N n-[5-[[5-chloro-4-[2-[2-(dimethylamino)-2-oxoacetyl]anilino]pyrimidin-2-yl]amino]-2-cyclopentyloxyphenyl]prop-2-enamide Chemical compound CN(C)C(=O)C(=O)C1=CC=CC=C1NC1=NC(NC=2C=C(NC(=O)C=C)C(OC3CCCC3)=CC=2)=NC=C1Cl YLORQIIPEBGMJH-UHFFFAOYSA-N 0.000 claims 1
- ZWECPWDKNQOSQQ-UHFFFAOYSA-N n-[5-[[5-chloro-4-[2-[2-(dimethylamino)-2-oxoacetyl]anilino]pyrimidin-2-yl]amino]-2-cyclopropyloxyphenyl]prop-2-enamide Chemical compound CN(C)C(=O)C(=O)C1=CC=CC=C1NC1=NC(NC=2C=C(NC(=O)C=C)C(OC3CC3)=CC=2)=NC=C1Cl ZWECPWDKNQOSQQ-UHFFFAOYSA-N 0.000 claims 1
- LUIUMZOKTAQVPT-UHFFFAOYSA-N n-[5-[[5-chloro-4-[2-[2-(dimethylamino)-2-oxoacetyl]anilino]pyrimidin-2-yl]amino]-2-fluoro-4-methoxyphenyl]prop-2-enamide Chemical compound COC1=CC(F)=C(NC(=O)C=C)C=C1NC1=NC=C(Cl)C(NC=2C(=CC=CC=2)C(=O)C(=O)N(C)C)=N1 LUIUMZOKTAQVPT-UHFFFAOYSA-N 0.000 claims 1
- DDNLSAZMIXQCQD-UHFFFAOYSA-N n-[5-[[5-chloro-4-[2-[2-(dimethylamino)-2-oxoacetyl]anilino]pyrimidin-2-yl]amino]-2-methoxyphenyl]prop-2-enamide Chemical compound C1=C(NC(=O)C=C)C(OC)=CC=C1NC1=NC=C(Cl)C(NC=2C(=CC=CC=2)C(=O)C(=O)N(C)C)=N1 DDNLSAZMIXQCQD-UHFFFAOYSA-N 0.000 claims 1
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- RHWLUCXWTWQGHA-UHFFFAOYSA-N n-[5-[[5-chloro-4-[2-[2-(dimethylamino)-2-oxoacetyl]anilino]pyrimidin-2-yl]amino]-4-methoxy-2-(3-morpholin-4-ylpropoxy)phenyl]prop-2-enamide Chemical compound C=CC(=O)NC=1C=C(NC=2N=C(NC=3C(=CC=CC=3)C(=O)C(=O)N(C)C)C(Cl)=CN=2)C(OC)=CC=1OCCCN1CCOCC1 RHWLUCXWTWQGHA-UHFFFAOYSA-N 0.000 claims 1
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- ZJSKEZXEVXVMDS-UHFFFAOYSA-N n-[5-[[5-chloro-4-[2-[2-(methylamino)-2-oxoacetyl]anilino]pyrimidin-2-yl]amino]-4-fluoro-2-methoxyphenyl]prop-2-enamide Chemical compound CNC(=O)C(=O)C1=CC=CC=C1NC1=NC(NC=2C(=CC(OC)=C(NC(=O)C=C)C=2)F)=NC=C1Cl ZJSKEZXEVXVMDS-UHFFFAOYSA-N 0.000 claims 1
- BBYTXTSYJQMNME-UHFFFAOYSA-N n-[5-[[5-chloro-4-[2-[2-(methylamino)-2-oxoacetyl]anilino]pyrimidin-2-yl]amino]-4-methoxy-2-(3-morpholin-4-ylpropoxy)phenyl]prop-2-enamide Chemical compound CNC(=O)C(=O)C1=CC=CC=C1NC1=NC(NC=2C(=CC(OCCCN3CCOCC3)=C(NC(=O)C=C)C=2)OC)=NC=C1Cl BBYTXTSYJQMNME-UHFFFAOYSA-N 0.000 claims 1
- HKNYNUXSBRUGNV-UHFFFAOYSA-N n-[5-[[5-chloro-4-[2-[2-(methylamino)-2-oxoacetyl]anilino]pyrimidin-2-yl]amino]-4-methoxy-2-(4-methylpiperazin-1-yl)phenyl]prop-2-enamide Chemical compound CNC(=O)C(=O)C1=CC=CC=C1NC1=NC(NC=2C(=CC(=C(NC(=O)C=C)C=2)N2CCN(C)CC2)OC)=NC=C1Cl HKNYNUXSBRUGNV-UHFFFAOYSA-N 0.000 claims 1
- UJROFNGOCICAHD-UHFFFAOYSA-N n-[5-[[5-chloro-4-[2-[2-[2-(dimethylamino)ethyl-methylamino]-2-oxoacetyl]anilino]pyrimidin-2-yl]amino]-2-methoxyphenyl]prop-2-enamide Chemical compound C1=C(NC(=O)C=C)C(OC)=CC=C1NC1=NC=C(Cl)C(NC=2C(=CC=CC=2)C(=O)C(=O)N(C)CCN(C)C)=N1 UJROFNGOCICAHD-UHFFFAOYSA-N 0.000 claims 1
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| DK2350075T3 (da) | 2008-09-22 | 2014-05-26 | Array Biopharma Inc | Substituerede imidazo[1,2b]pyridazinforbindelser som trk-kinase-inhibitorer |
| PT3106463T (pt) | 2008-10-22 | 2018-05-18 | Array Biopharma Inc | Compostos de pirazolo[1,5-]pirimidina substituídos como inibidores de cinase trk |
| AR077468A1 (es) | 2009-07-09 | 2011-08-31 | Array Biopharma Inc | Compuestos de pirazolo (1,5 -a) pirimidina sustituidos como inhibidores de trk- quinasa |
| RU2735545C2 (ru) | 2010-05-20 | 2020-11-03 | Эррэй Биофарма Инк. | Макроциклические соединения в качестве ингибиторов киназы trk |
| EP3218380B1 (en) | 2014-11-16 | 2021-03-17 | Array Biopharma, Inc. | Preparation of a crystalline form of (s)-n-(5-((r)-2-(2,5-difluorophenyl)-pyrrolidin-1-yl)-pyrazolo[1,5-a]pyrimidin-3-yl)-3-hydroxypyrrolidine-1-carboxamide hydrogen sulfate |
| CN106146525B (zh) * | 2015-04-10 | 2018-11-02 | 山东轩竹医药科技有限公司 | 三并环类间变性淋巴瘤激酶抑制剂 |
| CN104803925B (zh) * | 2015-04-16 | 2018-01-12 | 温州医科大学 | 一类以fgfr为靶点的2，4，5‑三取代嘧啶类化合物及其制备方法和用途 |
| JP6457697B2 (ja) * | 2015-04-29 | 2019-01-23 | カントン チョンション ファーマシューティカル カンパニー，リミティド | キナーゼ阻害剤としての縮合環式または三環式アリールピリミジン化合物 |
| CN106187915A (zh) * | 2015-05-27 | 2016-12-07 | 上海翰森生物医药科技有限公司 | 具有alk与egfr双重活性的抑制剂及其制备方法和应用 |
| CN105017160B (zh) * | 2015-06-24 | 2017-12-29 | 温州医科大学 | 一种嘧啶类egfrt790m抑制剂及其合成方法和应用 |
| TN2019000271A1 (en) | 2015-10-26 | 2021-01-07 | Univ Colorado Regents | Point mutations in trk inhibitor-resistant cancer and methods relating to the same |
| TW201718583A (zh) * | 2015-11-23 | 2017-06-01 | Nanjing Sanhome Pharmaceutical Co Ltd | 新的表皮生長因子受體抑制劑及其應用 |
| CN106883213B (zh) * | 2015-12-15 | 2021-04-20 | 合肥中科普瑞昇生物医药科技有限公司 | 一种egfr和alk激酶的双重抑制剂 |
| CN106928150B (zh) * | 2015-12-31 | 2020-07-31 | 恩瑞生物医药科技（上海）有限公司 | 丙烯酰胺苯胺衍生物及其药学上的应用 |
| US10045991B2 (en) | 2016-04-04 | 2018-08-14 | Loxo Oncology, Inc. | Methods of treating pediatric cancers |
| IL304018A (en) | 2016-04-04 | 2023-08-01 | Loxo Oncology Inc | Liquid formulations of (S)-N-(5-((R)-2-(5,2-difluorophenyl)-pyrrolidine-1-yl)-pyrazolo[5,1-A]pyrimidin-3-yl)-3 -hydroxypyrrolidine-1-carboxamide |
| ES2952056T3 (es) | 2016-05-18 | 2023-10-26 | 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 |
| WO2018019252A1 (en) * | 2016-07-26 | 2018-02-01 | Jacobio Pharmaceuticals Co., Ltd. | Novel fused pyridine derivatives useful as fak/aurora kinase inhibitors |
| JOP20190092A1 (ar) | 2016-10-26 | 2019-04-25 | Array Biopharma Inc | عملية لتحضير مركبات بيرازولو[1، 5-a]بيريميدين وأملاح منها |
| JOP20190213A1 (ar) | 2017-03-16 | 2019-09-16 | Array Biopharma Inc | مركبات حلقية ضخمة كمثبطات لكيناز ros1 |
| TWI798334B (zh) * | 2018-01-31 | 2023-04-11 | 大陸商迪哲（江蘇）醫藥股份有限公司 | Ｅｒｂｂ／ｂｔｋ抑制劑 |
| CN110372664A (zh) * | 2018-04-13 | 2019-10-25 | 华东理工大学 | 选择性jak2抑制剂及其应用 |
| US10644385B1 (en) * | 2019-03-14 | 2020-05-05 | L3Harris Technologies, Inc. | Wideband antenna system components in rotary aircraft rotors |
| SG11202110085TA (en) | 2019-05-31 | 2021-10-28 | Sichuan Haisco Pharmaceutical Co Ltd | Btk inhibitor ring derivative, preparation method therefor and pharmaceutical application thereof |
| KR102168179B1 (ko) | 2019-10-31 | 2020-10-20 | 주식회사 온코빅스 | 암세포 성장 억제 효과를 나타내는 신규한 헤테로 고리 치환 피리미딘 유도체 및 그를 포함하는 약제학적 조성물 |
| WO2021142408A1 (en) | 2020-01-11 | 2021-07-15 | Institute For Cancer Research D/B/A The Research Institute Of Fox Chase Cancer Center | Estrogen metabolite levels and cancer driver gene mutations in lung cancer risk stratification and treatment |
| KR20240046817A (ko) * | 2020-08-28 | 2024-04-09 | 이스트 차이나 유니버시티 오브 사이언스 앤드 테크놀로지 | 돌연변이형 egfr을 억제하는 화합물 및 이의 적용 |
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| GB0305929D0 (en) * | 2003-03-14 | 2003-04-23 | Novartis Ag | Organic compounds |
| BR122019017579B8 (pt) * | 2003-08-15 | 2021-07-27 | Novartis Ag | 2,4-pirimidinadiaminas, seus usos, combinação e composição farmacêutica |
| ME00811B (me) * | 2006-12-08 | 2012-03-20 | Novartis Ag | JEDINJENJA l KOMPOZICIJE KAO INHIBITORI PROTEIN KINAZE |
| US7834024B2 (en) * | 2007-03-26 | 2010-11-16 | Rigel Pharmaceuticals, Inc. | Compositions and methods for inhibition of the JAK pathway |
| US7989465B2 (en) * | 2007-10-19 | 2011-08-02 | Avila Therapeutics, Inc. | 4,6-disubstituted pyrimidines useful as kinase inhibitors |
| SG10201510696RA (en) * | 2008-06-27 | 2016-01-28 | Celgene Avilomics Res Inc | Heteroaryl compounds and uses thereof |
| AR074209A1 (es) | 2008-11-24 | 2010-12-29 | Boehringer Ingelheim Int | Derivados de pirimidina utiles para el tratamiento del cancer |
| US20130137709A1 (en) * | 2010-05-05 | 2013-05-30 | Nathanael S. Gray | Compounds that modulate EGFR activity and methods for treating or preventing conditions therewith |
| BR112013019643B1 (pt) * | 2011-02-02 | 2022-04-19 | Novartis Ag | Uso de inibidores de álcali |
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