JP2016515606A5 - - Google Patents
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- JP2016515606A5 JP2016515606A5 JP2016505888A JP2016505888A JP2016515606A5 JP 2016515606 A5 JP2016515606 A5 JP 2016515606A5 JP 2016505888 A JP2016505888 A JP 2016505888A JP 2016505888 A JP2016505888 A JP 2016505888A JP 2016515606 A5 JP2016515606 A5 JP 2016515606A5
- Authority
- JP
- Japan
- Prior art keywords
- methoxy
- ethoxy
- oxy
- tert
- butyl
- 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.)
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- -1 H Chemical group 0.000 claims 55
- 125000000217 alkyl group Chemical group 0.000 claims 48
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 36
- 150000001875 compounds Chemical class 0.000 claims 36
- 125000005843 halogen group Chemical group 0.000 claims 29
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 29
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 22
- 125000003545 alkoxy group Chemical group 0.000 claims 16
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 13
- 125000001424 substituent group Chemical group 0.000 claims 13
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 12
- 229910052799 carbon Inorganic materials 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims 11
- 125000002947 alkylene group Chemical group 0.000 claims 10
- 229910052760 oxygen Inorganic materials 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 10
- 239000012453 solvate Substances 0.000 claims 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 9
- 230000000155 isotopic effect Effects 0.000 claims 9
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 9
- 229910052717 sulfur Inorganic materials 0.000 claims 8
- 238000006243 chemical reaction Methods 0.000 claims 6
- 125000001153 fluoro group Chemical group F* 0.000 claims 6
- 125000005842 heteroatom Chemical group 0.000 claims 6
- 238000002360 preparation method Methods 0.000 claims 6
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 5
- 239000004202 carbamide Substances 0.000 claims 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 5
- 229920006395 saturated elastomer Polymers 0.000 claims 5
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 4
- 125000004429 atom Chemical group 0.000 claims 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 4
- 239000012634 fragment Substances 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 208000027866 inflammatory disease Diseases 0.000 claims 4
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 3
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims 3
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 238000009472 formulation Methods 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 2
- BHNGTBAKKDCSHZ-UHFFFAOYSA-N 3-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-5-methoxy-n-(2-morpholin-4-ylethyl)benzamide Chemical compound C=1C(C(=O)NCCN2CCOCC2)=CC(OC)=CC=1NC(N=CC=1)=CC=1OC(C1=CC=CC=C11)=CC=C1NC(=O)NC1=CC(C(C)(C)C)=CC(NS(C)(=O)=O)=C1OC BHNGTBAKKDCSHZ-UHFFFAOYSA-N 0.000 claims 2
- NIMKGKUGIJVPTM-UHFFFAOYSA-N 3-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-5-methoxy-n-(3-morpholin-4-ylpropyl)benzamide Chemical compound C=1C(C(=O)NCCCN2CCOCC2)=CC(OC)=CC=1NC(N=CC=1)=CC=1OC(C1=CC=CC=C11)=CC=C1NC(=O)NC1=CC(C(C)(C)C)=CC(NS(C)(=O)=O)=C1OC NIMKGKUGIJVPTM-UHFFFAOYSA-N 0.000 claims 2
- RAYAYIHOCMLVRR-UHFFFAOYSA-N 3-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-5-methoxy-n-[2-[2-(2-methoxyethoxy)ethoxy]ethyl]benzamide Chemical compound COC1=CC(C(=O)NCCOCCOCCOC)=CC(NC=2N=CC=C(OC=3C4=CC=CC=C4C(NC(=O)NC=4C(=C(NS(C)(=O)=O)C=C(C=4)C(C)(C)C)OC)=CC=3)C=2)=C1 RAYAYIHOCMLVRR-UHFFFAOYSA-N 0.000 claims 2
- FWXVGKSWZJEPQI-UHFFFAOYSA-N 3-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyrimidin-2-yl]amino]-5-ethynyl-n-[2-[2-(2-methoxyethoxy)ethoxy]ethyl]benzamide Chemical compound C#CC1=CC(C(=O)NCCOCCOCCOC)=CC(NC=2N=C(OC=3C4=CC=CC=C4C(NC(=O)NC=4C(=C(NS(C)(=O)=O)C=C(C=4)C(C)(C)C)OC)=CC=3)C=CN=2)=C1 FWXVGKSWZJEPQI-UHFFFAOYSA-N 0.000 claims 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- 206010009900 Colitis ulcerative Diseases 0.000 claims 2
- 208000011231 Crohn disease Diseases 0.000 claims 2
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 2
- 206010046851 Uveitis Diseases 0.000 claims 2
- 239000002671 adjuvant Substances 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 201000008937 atopic dermatitis Diseases 0.000 claims 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 201000005667 central retinal vein occlusion Diseases 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 208000004644 retinal vein occlusion Diseases 0.000 claims 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- XEIYTKCNVAGUBD-UHFFFAOYSA-N 1-(3-amino-5-tert-butyl-2-methoxyphenyl)-3-[4-[2-[3-methoxy-5-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]anilino]pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound COC1=CC(OCCOCCOCCOC)=CC(NC=2N=C(OC=3C4=CC=CC=C4C(NC(=O)NC=4C(=C(N)C=C(C=4)C(C)(C)C)OC)=CC=3)C=CN=2)=C1 XEIYTKCNVAGUBD-UHFFFAOYSA-N 0.000 claims 1
- RZHXQYGUTLBKMJ-UHFFFAOYSA-N 1-(5-tert-butyl-2-oxo-3h-1,3-benzoxazol-7-yl)-3-[4-[2-[3-methoxy-5-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]anilino]pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound COC1=CC(OCCOCCOCCOC)=CC(NC=2N=C(OC=3C4=CC=CC=C4C(NC(=O)NC=4C=5OC(=O)NC=5C=C(C=4)C(C)(C)C)=CC=3)C=CN=2)=C1 RZHXQYGUTLBKMJ-UHFFFAOYSA-N 0.000 claims 1
- GPUULLKUPYPMEV-UHFFFAOYSA-N 1-(5-tert-butyl-3-cyano-2-methoxyphenyl)-3-[4-[2-[3-methoxy-5-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]anilino]pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound COC1=CC(OCCOCCOCCOC)=CC(NC=2N=C(OC=3C4=CC=CC=C4C(NC(=O)NC=4C(=C(C#N)C=C(C=4)C(C)(C)C)OC)=CC=3)C=CN=2)=C1 GPUULLKUPYPMEV-UHFFFAOYSA-N 0.000 claims 1
- VWZIUBUXROEOHM-UHFFFAOYSA-N 1-[4-(2-anilinopyridin-4-yl)oxynaphthalen-1-yl]-3-[5-tert-butyl-2-methoxy-3-(morpholin-4-ylsulfonylamino)phenyl]urea Chemical compound C1=C(C(C)(C)C)C=C(NS(=O)(=O)N2CCOCC2)C(OC)=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1OC(C=1)=CC=NC=1NC1=CC=CC=C1 VWZIUBUXROEOHM-UHFFFAOYSA-N 0.000 claims 1
- CBRIEUCHYNRMNT-UHFFFAOYSA-N 1-[4-[2-[3-methoxy-5-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]anilino]pyrimidin-4-yl]oxynaphthalen-1-yl]-3-(2-methoxy-5-morpholin-4-ylphenyl)urea Chemical compound COC1=CC(OCCOCCOCCOC)=CC(NC=2N=C(OC=3C4=CC=CC=C4C(NC(=O)NC=4C(=CC=C(C=4)N4CCOCC4)OC)=CC=3)C=CN=2)=C1 CBRIEUCHYNRMNT-UHFFFAOYSA-N 0.000 claims 1
- OUROWULXWNIHIF-UHFFFAOYSA-N 1-[5-tert-butyl-2-methoxy-3-(1,3,4-oxadiazol-2-yl)phenyl]-3-[4-[2-[3-methoxy-5-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]anilino]pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound COC1=CC(OCCOCCOCCOC)=CC(NC=2N=C(OC=3C4=CC=CC=C4C(NC(=O)NC=4C(=C(C=5OC=NN=5)C=C(C=4)C(C)(C)C)OC)=CC=3)C=CN=2)=C1 OUROWULXWNIHIF-UHFFFAOYSA-N 0.000 claims 1
- XWCPBCVFAOFEEK-UHFFFAOYSA-N 1-[5-tert-butyl-2-methoxy-3-(1h-triazol-5-yl)phenyl]-3-[4-[2-[3-methoxy-5-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]anilino]pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound COC1=CC(OCCOCCOCCOC)=CC(NC=2N=C(OC=3C4=CC=CC=C4C(NC(=O)NC=4C(=C(C=5NN=NC=5)C=C(C=4)C(C)(C)C)OC)=CC=3)C=CN=2)=C1 XWCPBCVFAOFEEK-UHFFFAOYSA-N 0.000 claims 1
- HARDADFQDKOPFH-UHFFFAOYSA-N 1-[5-tert-butyl-2-methoxy-3-(morpholin-4-ylsulfonylamino)phenyl]-3-[4-[2-[3-methoxy-5-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]anilino]pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound COC1=CC(OCCOCCOCCOC)=CC(NC=2N=C(OC=3C4=CC=CC=C4C(NC(=O)NC=4C(=C(NS(=O)(=O)N5CCOCC5)C=C(C=4)C(C)(C)C)OC)=CC=3)C=CN=2)=C1 HARDADFQDKOPFH-UHFFFAOYSA-N 0.000 claims 1
- HXKBJZWDETZQLS-UHFFFAOYSA-N 1-[5-tert-butyl-2-methoxy-3-(piperidin-1-ylsulfonylamino)phenyl]-3-[4-[2-[3-methoxy-5-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]anilino]pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound COC1=CC(OCCOCCOCCOC)=CC(NC=2N=C(OC=3C4=CC=CC=C4C(NC(=O)NC=4C(=C(NS(=O)(=O)N5CCCCC5)C=C(C=4)C(C)(C)C)OC)=CC=3)C=CN=2)=C1 HXKBJZWDETZQLS-UHFFFAOYSA-N 0.000 claims 1
- PKOUTHZCBPYDLA-UHFFFAOYSA-N 1-[5-tert-butyl-2-methoxy-3-(pyrimidin-2-ylamino)phenyl]-3-[4-[2-[3-methoxy-5-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]anilino]pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound COC1=CC(OCCOCCOCCOC)=CC(NC=2N=C(OC=3C4=CC=CC=C4C(NC(=O)NC=4C(=C(NC=5N=CC=CN=5)C=C(C=4)C(C)(C)C)OC)=CC=3)C=CN=2)=C1 PKOUTHZCBPYDLA-UHFFFAOYSA-N 0.000 claims 1
- AVUWEQZRGUEGQI-UHFFFAOYSA-N 1-[5-tert-butyl-2-methoxy-3-(trifluoromethylsulfonylamino)phenyl]-3-[4-[2-[3-methoxy-5-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]anilino]pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound COC1=CC(OCCOCCOCCOC)=CC(NC=2N=C(OC=3C4=CC=CC=C4C(NC(=O)NC=4C(=C(NS(=O)(=O)C(F)(F)F)C=C(C=4)C(C)(C)C)OC)=CC=3)C=CN=2)=C1 AVUWEQZRGUEGQI-UHFFFAOYSA-N 0.000 claims 1
- IVYTVFJSLCFTSX-UHFFFAOYSA-N 1-[5-tert-butyl-3-(cyclohexylsulfonylamino)-2-methoxyphenyl]-3-[4-[2-[3-methoxy-5-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]anilino]pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound COC1=CC(OCCOCCOCCOC)=CC(NC=2N=C(OC=3C4=CC=CC=C4C(NC(=O)NC=4C(=C(NS(=O)(=O)C5CCCCC5)C=C(C=4)C(C)(C)C)OC)=CC=3)C=CN=2)=C1 IVYTVFJSLCFTSX-UHFFFAOYSA-N 0.000 claims 1
- QOWKUFBXVJBQHQ-UHFFFAOYSA-N 1-[5-tert-butyl-3-(dimethylsulfamoylamino)-2-methoxyphenyl]-3-[4-[2-[3-methoxy-5-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]anilino]pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound COC1=CC(OCCOCCOCCOC)=CC(NC=2N=C(OC=3C4=CC=CC=C4C(NC(=O)NC=4C(=C(NS(=O)(=O)N(C)C)C=C(C=4)C(C)(C)C)OC)=CC=3)C=CN=2)=C1 QOWKUFBXVJBQHQ-UHFFFAOYSA-N 0.000 claims 1
- GPYGSYSPXHEXTJ-UHFFFAOYSA-N 1-[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]-3-[2,3-dichloro-4-[2-[3-methoxy-5-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]anilino]pyrimidin-4-yl]oxyphenyl]urea Chemical compound COC1=CC(OCCOCCOCCOC)=CC(NC=2N=C(OC=3C(=C(Cl)C(NC(=O)NC=4C(=C(NS(C)(=O)=O)C=C(C=4)C(C)(C)C)OC)=CC=3)Cl)C=CN=2)=C1 GPYGSYSPXHEXTJ-UHFFFAOYSA-N 0.000 claims 1
- DWIZOBLALXNUQT-UHFFFAOYSA-N 1-[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]-3-[4-[2-(3-cyclopropylsulfonyl-5-methoxyanilino)pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C=1C(S(=O)(=O)C2CC2)=CC(OC)=CC=1NC(N=1)=NC=CC=1OC(C1=CC=CC=C11)=CC=C1NC(=O)NC1=CC(C(C)(C)C)=CC(NS(C)(=O)=O)=C1OC DWIZOBLALXNUQT-UHFFFAOYSA-N 0.000 claims 1
- ZVHJSCQINRIIPI-UHFFFAOYSA-N 1-[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]-3-[4-[2-[3-(cyclopropanecarbonyl)-5-methoxyanilino]pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C=1C(C(=O)C2CC2)=CC(OC)=CC=1NC(N=1)=NC=CC=1OC(C1=CC=CC=C11)=CC=C1NC(=O)NC1=CC(C(C)(C)C)=CC(NS(C)(=O)=O)=C1OC ZVHJSCQINRIIPI-UHFFFAOYSA-N 0.000 claims 1
- AXWACQOPPLIPNN-UHFFFAOYSA-N 1-[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]-3-[4-[2-[3-(hydroxymethyl)-5-methoxyanilino]pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound COC1=CC(CO)=CC(NC=2N=CC=C(OC=3C4=CC=CC=C4C(NC(=O)NC=4C(=C(NS(C)(=O)=O)C=C(C=4)C(C)(C)C)OC)=CC=3)C=2)=C1 AXWACQOPPLIPNN-UHFFFAOYSA-N 0.000 claims 1
- DBKIZDKUZBXXRO-UHFFFAOYSA-N 1-[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]-3-[4-[2-[3-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]-5-methoxyanilino]pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound OCCOCCOCCOC1=CC(OC)=CC(NC=2N=CC=C(OC=3C4=CC=CC=C4C(NC(=O)NC=4C(=C(NS(C)(=O)=O)C=C(C=4)C(C)(C)C)OC)=CC=3)C=2)=C1 DBKIZDKUZBXXRO-UHFFFAOYSA-N 0.000 claims 1
- DRXSEANATMYVSO-UHFFFAOYSA-N 1-[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]-3-[4-[2-[3-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]-5-methoxyanilino]pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound OCCOCCOCCOC1=CC(OC)=CC(NC=2N=C(OC=3C4=CC=CC=C4C(NC(=O)NC=4C(=C(NS(C)(=O)=O)C=C(C=4)C(C)(C)C)OC)=CC=3)C=CN=2)=C1 DRXSEANATMYVSO-UHFFFAOYSA-N 0.000 claims 1
- MYLRWMCTBKFTSO-UHFFFAOYSA-N 1-[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]-3-[4-[2-[3-methoxy-5-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]anilino]pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound COC1=CC(OCCOCCOCCOC)=CC(NC=2N=CC=C(OC=3C4=CC=CC=C4C(NC(=O)NC=4C(=C(NS(C)(=O)=O)C=C(C=4)C(C)(C)C)OC)=CC=3)C=2)=C1 MYLRWMCTBKFTSO-UHFFFAOYSA-N 0.000 claims 1
- IEHFKZAAIWSDQM-UHFFFAOYSA-N 1-[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]-3-[4-[2-[3-methoxy-5-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]anilino]pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound COC1=CC(OCCOCCOCCOC)=CC(NC=2N=C(OC=3C4=CC=CC=C4C(NC(=O)NC=4C(=C(NS(C)(=O)=O)C=C(C=4)C(C)(C)C)OC)=CC=3)C=CN=2)=C1 IEHFKZAAIWSDQM-UHFFFAOYSA-N 0.000 claims 1
- VZEBZVKYQRSFDD-UHFFFAOYSA-N 1-[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]-3-[4-[2-[3-methoxy-5-[2-[2-(2-morpholin-4-ylethoxy)ethoxy]ethoxy]anilino]pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C=1C(OCCOCCOCCN2CCOCC2)=CC(OC)=CC=1NC(N=1)=NC=CC=1OC(C1=CC=CC=C11)=CC=C1NC(=O)NC1=CC(C(C)(C)C)=CC(NS(C)(=O)=O)=C1OC VZEBZVKYQRSFDD-UHFFFAOYSA-N 0.000 claims 1
- BYQPTCVIKWPGJG-UHFFFAOYSA-N 1-[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]-3-[4-[2-[3-methoxy-5-[2-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]anilino]pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound COC1=CC(OCCOCCOCCOCCOCCOCCOCCOC)=CC(NC=2N=CC=C(OC=3C4=CC=CC=C4C(NC(=O)NC=4C(=C(NS(C)(=O)=O)C=C(C=4)C(C)(C)C)OC)=CC=3)C=2)=C1 BYQPTCVIKWPGJG-UHFFFAOYSA-N 0.000 claims 1
- KWEVSNRXKHUTLB-UHFFFAOYSA-N 1-[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]-3-[4-[2-[3-methoxy-5-[2-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]anilino]pyrimidin-4-yl]oxynaphthalen-1-yl]urea Chemical compound COC1=CC(OCCOCCOCCOCCOCCOCCOCCOC)=CC(NC=2N=C(OC=3C4=CC=CC=C4C(NC(=O)NC=4C(=C(NS(C)(=O)=O)C=C(C=4)C(C)(C)C)OC)=CC=3)C=CN=2)=C1 KWEVSNRXKHUTLB-UHFFFAOYSA-N 0.000 claims 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- IMIBHFMPIQXDLN-UHFFFAOYSA-N 2-methoxy-3-[[4-[2-[3-methoxy-5-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]anilino]pyrimidin-4-yl]oxynaphthalen-1-yl]carbamoylamino]-n-methyl-5-morpholin-4-ylbenzamide Chemical compound COC=1C(C(=O)NC)=CC(N2CCOCC2)=CC=1NC(=O)NC(C1=CC=CC=C11)=CC=C1OC(N=1)=CC=NC=1NC1=CC(OC)=CC(OCCOCCOCCOC)=C1 IMIBHFMPIQXDLN-UHFFFAOYSA-N 0.000 claims 1
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- XZMCZGOJOFAJCJ-UHFFFAOYSA-N 3-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-5-methoxy-N-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethyl]benzamide Chemical compound COC1=CC(C(=O)NCCOCCOCCOCCOC)=CC(NC=2N=CC=C(OC=3C4=CC=CC=C4C(NC(=O)NC=4C(=C(NS(C)(=O)=O)C=C(C=4)C(C)(C)C)OC)=CC=3)C=2)=C1 XZMCZGOJOFAJCJ-UHFFFAOYSA-N 0.000 claims 1
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- GUULINOWBZUTJL-UHFFFAOYSA-N 3-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-N-[2-(2,2-dimethylmorpholin-4-yl)ethyl]-5-methoxybenzamide Chemical compound C=1C(C(=O)NCCN2CC(C)(C)OCC2)=CC(OC)=CC=1NC(N=CC=1)=CC=1OC(C1=CC=CC=C11)=CC=C1NC(=O)NC1=CC(C(C)(C)C)=CC(NS(C)(=O)=O)=C1OC GUULINOWBZUTJL-UHFFFAOYSA-N 0.000 claims 1
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- TYYKWQBVMJUBOB-UHFFFAOYSA-N 3-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]amino]-N-[2-(4-hydroxypiperidin-1-yl)ethyl]-5-methoxybenzamide Chemical compound C=1C(C(=O)NCCN2CCC(O)CC2)=CC(OC)=CC=1NC(N=CC=1)=CC=1OC(C1=CC=CC=C11)=CC=C1NC(=O)NC1=CC(C(C)(C)C)=CC(NS(C)(=O)=O)=C1OC TYYKWQBVMJUBOB-UHFFFAOYSA-N 0.000 claims 1
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- CYKJKKJPMBDBAT-UHFFFAOYSA-N 3-[[4-[4-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoylamino]naphthalen-1-yl]oxypyrimidin-2-yl]amino]-5-ethynyl-n-(2-morpholin-4-ylethyl)benzamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1OC1=CC=NC(NC=2C=C(C=C(C=2)C#C)C(=O)NCCN2CCOCC2)=N1 CYKJKKJPMBDBAT-UHFFFAOYSA-N 0.000 claims 1
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- KADSTJJZALTROR-UHFFFAOYSA-N 3-tert-butyl-5-[[4-[2-[3-methoxy-5-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]anilino]pyrimidin-4-yl]oxynaphthalen-1-yl]carbamoylamino]-N-methylbenzamide Chemical compound CC(C)(C)C1=CC(C(=O)NC)=CC(NC(=O)NC=2C3=CC=CC=C3C(OC=3N=C(NC=4C=C(OCCOCCOCCOC)C=C(OC)C=4)N=CC=3)=CC=2)=C1 KADSTJJZALTROR-UHFFFAOYSA-N 0.000 claims 1
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- JMZYKNIQZZGAOQ-UHFFFAOYSA-N 5-tert-butyl-2-methoxy-3-[[4-[2-[3-methoxy-5-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]anilino]pyridin-4-yl]oxynaphthalen-1-yl]carbamoylamino]-n-methylbenzamide Chemical compound CNC(=O)C1=CC(C(C)(C)C)=CC(NC(=O)NC=2C3=CC=CC=C3C(OC=3C=C(NC=4C=C(OCCOCCOCCOC)C=C(OC)C=4)N=CC=3)=CC=2)=C1OC JMZYKNIQZZGAOQ-UHFFFAOYSA-N 0.000 claims 1
- XLMGQVCEWMWIIG-UHFFFAOYSA-N 5-tert-butyl-2-methoxy-3-[[4-[2-[3-methoxy-5-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]anilino]pyridin-4-yl]oxynaphthalen-1-yl]carbamoylamino]benzamide Chemical compound COC1=CC(OCCOCCOCCOC)=CC(NC=2N=CC=C(OC=3C4=CC=CC=C4C(NC(=O)NC=4C(=C(C(N)=O)C=C(C=4)C(C)(C)C)OC)=CC=3)C=2)=C1 XLMGQVCEWMWIIG-UHFFFAOYSA-N 0.000 claims 1
- HWZCSBMMDQCHFJ-UHFFFAOYSA-N 5-tert-butyl-2-methoxy-3-[[4-[2-[3-methoxy-5-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]anilino]pyrimidin-4-yl]oxynaphthalen-1-yl]carbamoylamino]-n-propan-2-ylbenzamide Chemical compound COC1=CC(OCCOCCOCCOC)=CC(NC=2N=C(OC=3C4=CC=CC=C4C(NC(=O)NC=4C(=C(C(=O)NC(C)C)C=C(C=4)C(C)(C)C)OC)=CC=3)C=CN=2)=C1 HWZCSBMMDQCHFJ-UHFFFAOYSA-N 0.000 claims 1
- XEFBBQIBHYFSDW-UHFFFAOYSA-N 5-tert-butyl-3-[[4-[2-[3-(hydroxymethyl)-5-methoxyanilino]pyridin-4-yl]oxynaphthalen-1-yl]carbamoylamino]-2-methoxy-N-methylbenzamide Chemical compound CNC(=O)C1=CC(C(C)(C)C)=CC(NC(=O)NC=2C3=CC=CC=C3C(OC=3C=C(NC=4C=C(OC)C=C(CO)C=4)N=CC=3)=CC=2)=C1OC XEFBBQIBHYFSDW-UHFFFAOYSA-N 0.000 claims 1
- RXXPIRGHDOIFNF-UHFFFAOYSA-N 5-tert-butyl-3-[[4-[2-[3-(hydroxymethyl)-5-methoxyanilino]pyridin-4-yl]oxynaphthalen-1-yl]carbamoylamino]-2-methoxybenzamide Chemical compound COC1=CC(CO)=CC(NC=2N=CC=C(OC=3C4=CC=CC=C4C(NC(=O)NC=4C(=C(C(N)=O)C=C(C=4)C(C)(C)C)OC)=CC=3)C=2)=C1 RXXPIRGHDOIFNF-UHFFFAOYSA-N 0.000 claims 1
- KZSAULBVLYTWGY-UHFFFAOYSA-N 5-tert-butyl-3-[[4-[2-[3-ethynyl-5-(2-morpholin-4-ylethylcarbamoyl)anilino]pyridin-4-yl]oxynaphthalen-1-yl]carbamoylamino]-2-methoxy-n-methylbenzamide Chemical compound CNC(=O)C1=CC(C(C)(C)C)=CC(NC(=O)NC=2C3=CC=CC=C3C(OC=3C=C(NC=4C=C(C=C(C=4)C#C)C(=O)NCCN4CCOCC4)N=CC=3)=CC=2)=C1OC KZSAULBVLYTWGY-UHFFFAOYSA-N 0.000 claims 1
- KAEJJEOVKUZVFV-UHFFFAOYSA-N 5-tert-butyl-3-[[4-[2-[3-ethynyl-5-(2-morpholin-4-ylethylcarbamoyl)anilino]pyridin-4-yl]oxynaphthalen-1-yl]carbamoylamino]-2-methoxybenzamide Chemical compound C1=C(C(C)(C)C)C=C(C(N)=O)C(OC)=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1OC1=CC=NC(NC=2C=C(C=C(C=2)C#C)C(=O)NCCN2CCOCC2)=C1 KAEJJEOVKUZVFV-UHFFFAOYSA-N 0.000 claims 1
- VGHUYLNQBPEVLC-UHFFFAOYSA-N 5-tert-butyl-3-[[4-[2-[3-ethynyl-5-(2-morpholin-4-ylethylcarbamoyl)anilino]pyrimidin-4-yl]oxynaphthalen-1-yl]carbamoylamino]-2-methoxy-n-methylbenzamide Chemical compound CNC(=O)C1=CC(C(C)(C)C)=CC(NC(=O)NC=2C3=CC=CC=C3C(OC=3N=C(NC=4C=C(C=C(C=4)C#C)C(=O)NCCN4CCOCC4)N=CC=3)=CC=2)=C1OC VGHUYLNQBPEVLC-UHFFFAOYSA-N 0.000 claims 1
- BVSCAJCLADHYTE-UHFFFAOYSA-N 5-tert-butyl-3-[[4-[2-[3-ethynyl-5-(2-morpholin-4-ylethylcarbamoyl)anilino]pyrimidin-4-yl]oxynaphthalen-1-yl]carbamoylamino]-2-methoxybenzamide Chemical compound C1=C(C(C)(C)C)C=C(C(N)=O)C(OC)=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1OC1=CC=NC(NC=2C=C(C=C(C=2)C#C)C(=O)NCCN2CCOCC2)=N1 BVSCAJCLADHYTE-UHFFFAOYSA-N 0.000 claims 1
- HBXARKCGJMUAON-UHFFFAOYSA-N 5-tert-butyl-3-[[4-[2-[3-ethynyl-5-(hydroxymethyl)anilino]pyridin-4-yl]oxynaphthalen-1-yl]carbamoylamino]-2-methoxy-N-methylbenzamide Chemical compound CNC(=O)C1=CC(C(C)(C)C)=CC(NC(=O)NC=2C3=CC=CC=C3C(OC=3C=C(NC=4C=C(C=C(CO)C=4)C#C)N=CC=3)=CC=2)=C1OC HBXARKCGJMUAON-UHFFFAOYSA-N 0.000 claims 1
- WYCWMEMAUWDKFV-UHFFFAOYSA-N 5-tert-butyl-3-[[4-[2-[3-ethynyl-5-(hydroxymethyl)anilino]pyridin-4-yl]oxynaphthalen-1-yl]carbamoylamino]-2-methoxybenzamide Chemical compound C1=C(C(C)(C)C)C=C(C(N)=O)C(OC)=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1OC1=CC=NC(NC=2C=C(C=C(CO)C=2)C#C)=C1 WYCWMEMAUWDKFV-UHFFFAOYSA-N 0.000 claims 1
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| PT2763984T (pt) | 2011-10-03 | 2016-07-25 | Respivert Ltd | 1-pirazolil-3-(4-((2-anilinopirimidin-4-il)oxi)naftalen-1-il) ureias como inibidores da map cinase p38 |
| CN105968110B (zh) | 2011-12-09 | 2018-04-27 | 奇斯药制品公司 | 激酶抑制剂 |
| GB201214750D0 (en) * | 2012-08-17 | 2012-10-03 | Respivert Ltd | Compounds |
| US20150210722A1 (en) | 2012-08-29 | 2015-07-30 | Respivert Limited | Kinase inhibitors |
| GB201215357D0 (en) | 2012-08-29 | 2012-10-10 | Respivert Ltd | Compounds |
| WO2014033449A1 (en) | 2012-08-29 | 2014-03-06 | Respivert Limited | Kinase inhibitors |
| WO2014033447A2 (en) | 2012-08-29 | 2014-03-06 | Respivert Limited | Kinase inhibitors |
| US9732063B2 (en) | 2012-11-16 | 2017-08-15 | Respivert Limited | Kinase inhibitors |
| US20160016934A1 (en) | 2013-03-14 | 2016-01-21 | Respivert Limited | Kinase inhibitors |
| KR102283883B1 (ko) * | 2013-04-02 | 2021-07-29 | 옥슬러 액퀴지션즈 리미티드 | 키나제 저해제 |
| EP2981534B1 (en) | 2013-04-02 | 2017-07-19 | Topivert Pharma Limited | Kinase inhibitors based upon n-alkyl pyrazoles |
| CA2934199A1 (en) | 2013-12-20 | 2015-06-25 | Respivert Limited | Urea derivatives useful as kinase inhibitors |
| US9447076B2 (en) | 2014-02-14 | 2016-09-20 | Respivert Ltd. | Inhibitor of p38 map kinase |
| MA40775A (fr) | 2014-10-01 | 2017-08-08 | Respivert Ltd | Dérivé d'acide 4-(4-(4-phényluréido-naphtalén -1-yl) oxy-pyridin-2-yl) amino-benzoïque utilisé en tant qu'inhibiteur de la kinase p38 |
| CA3015978A1 (en) * | 2016-04-06 | 2017-10-12 | Topivert Pharma Limited | Kinase inhibitors |
-
2014
- 2014-04-01 KR KR1020157031292A patent/KR102283883B1/ko not_active Expired - Fee Related
- 2014-04-01 BR BR112015024678-8A patent/BR112015024678B1/pt not_active IP Right Cessation
- 2014-04-01 AU AU2014246870A patent/AU2014246870C1/en not_active Ceased
- 2014-04-01 ES ES14716378T patent/ES2856902T3/es active Active
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- 2014-04-01 JP JP2016505887A patent/JP6464384B2/ja not_active Expired - Fee Related
- 2014-04-01 EA EA201591907A patent/EA027782B1/ru not_active IP Right Cessation
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- 2014-04-01 EP EP14716378.6A patent/EP2981535B8/en active Active
- 2014-04-01 ES ES14715106T patent/ES2904277T3/es active Active
- 2014-04-01 WO PCT/GB2014/051018 patent/WO2014162122A1/en not_active Ceased
- 2014-04-01 MX MX2015013944A patent/MX363949B/es active IP Right Grant
- 2014-04-01 KR KR1020217023664A patent/KR102340654B1/ko not_active Expired - Fee Related
- 2014-04-01 CN CN201480031577.7A patent/CN105408315B/zh not_active Expired - Fee Related
- 2014-04-01 CN CN201480031484.4A patent/CN105246884B/zh not_active Expired - Fee Related
- 2014-04-01 WO PCT/GB2014/051022 patent/WO2014162126A1/en not_active Ceased
- 2014-04-01 MX MX2015013945A patent/MX363950B/es active IP Right Grant
- 2014-04-01 DK DK14715106.2T patent/DK2981526T3/da active
- 2014-04-01 EP EP14715106.2A patent/EP2981526B1/en active Active
- 2014-04-01 TW TW103112073A patent/TWI641592B/zh not_active IP Right Cessation
- 2014-04-01 DK DK14716378.6T patent/DK2981535T3/da active
- 2014-04-01 KR KR1020157031287A patent/KR102283876B1/ko not_active Expired - Fee Related
- 2014-04-01 AU AU2014246866A patent/AU2014246866B2/en not_active Ceased
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- 2014-04-01 JP JP2016505888A patent/JP6495238B2/ja not_active Expired - Fee Related
- 2014-04-01 CA CA2907663A patent/CA2907663A1/en not_active Abandoned
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