JP6121991B2 - Ｍｋｎｋ１キナーゼ阻害剤としてのアミノ置換イミダゾピリダジン - Google Patents

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Publication number

JP6121991B2

JP6121991B2 JP2014510768A JP2014510768A JP6121991B2 JP 6121991 B2 JP6121991 B2 JP 6121991B2 JP 2014510768 A JP2014510768 A JP 2014510768A JP 2014510768 A JP2014510768 A JP 2014510768A JP 6121991 B2 JP6121991 B2 JP 6121991B2

Authority

JP

Japan

Prior art keywords

group

nhr

alkyl

amino

imidazo

Prior art date

2011-05-17

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 Amino-substituted imidazopyridazines Chemical class 0.000 title claims description 293
• 102100026299 MAP kinase-interacting serine/threonine-protein kinase 1 Human genes 0.000 title description 28
• 101000573522 Homo sapiens MAP kinase-interacting serine/threonine-protein kinase 1 Proteins 0.000 title description 27
• 229940043355 kinase inhibitor Drugs 0.000 title description 6
• 239000003757 phosphotransferase inhibitor Substances 0.000 title description 6
• 150000001875 compounds Chemical class 0.000 claims description 328
• 125000001424 substituent group Chemical group 0.000 claims description 173
• 239000000203 mixture Substances 0.000 claims description 114
• 125000005843 halogen group Chemical group 0.000 claims description 104
• 238000000034 method Methods 0.000 claims description 104
• 125000003118 aryl group Chemical group 0.000 claims description 89
• 229910052799 carbon Inorganic materials 0.000 claims description 75
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 69
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 61
• 150000003839 salts Chemical class 0.000 claims description 61
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 58
• 125000001072 heteroaryl group Chemical group 0.000 claims description 54
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 52
• 206010028980 Neoplasm Diseases 0.000 claims description 50
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 50
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 48
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 39
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 38
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 37
• 239000012453 solvate Substances 0.000 claims description 36
• 201000010099 disease Diseases 0.000 claims description 34
• 125000006584 (C3-C10) heterocycloalkyl group Chemical group 0.000 claims description 33
• 238000011282 treatment Methods 0.000 claims description 31
• 150000001204 N-oxides Chemical class 0.000 claims description 26
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 24
• 230000001413 cellular effect Effects 0.000 claims description 22
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• 239000004480 active ingredient Substances 0.000 claims description 16
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 16
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• 238000002360 preparation method Methods 0.000 claims description 11
• 229910052794 bromium Inorganic materials 0.000 claims description 9
• 239000000460 chlorine Substances 0.000 claims description 9
• 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 claims description 9
• 230000002265 prevention Effects 0.000 claims description 9
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 8
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• 229910052801 chlorine Inorganic materials 0.000 claims description 8
• 150000004677 hydrates Chemical class 0.000 claims description 8
• 229910052740 iodine Inorganic materials 0.000 claims description 8
• 208000032839 leukemia Diseases 0.000 claims description 8
• 230000001404 mediated effect Effects 0.000 claims description 8
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• 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 8
• 239000003085 diluting agent Substances 0.000 claims description 7
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• 206010006187 Breast cancer Diseases 0.000 claims description 6
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• ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical group OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 6
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• REAUMEFIVWHGEV-KRWDZBQOSA-N (1R)-2-[[3-(4-methoxyfuro[3,2-c]pyridin-2-yl)imidazo[1,2-b]pyridazin-6-yl]amino]-1-phenylethanol Chemical compound C1([C@@H](O)CNC=2C=CC3=NC=C(N3N=2)C=2OC=3C=CN=C(C=3C=2)OC)=CC=CC=C1 REAUMEFIVWHGEV-KRWDZBQOSA-N 0.000 claims description 2
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• AEWCZIWKJPNHNP-GOSISDBHSA-N (1s)-2-[[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]amino]-1-phenylethanol Chemical compound C1([C@@H](CNC2=NN3C(C=4OC5=CC=CC=C5C=4)=CN=C3C=C2)O)=CC=CC=C1 AEWCZIWKJPNHNP-GOSISDBHSA-N 0.000 claims description 2
• REAUMEFIVWHGEV-QGZVFWFLSA-N (1s)-2-[[3-(4-methoxyfuro[3,2-c]pyridin-2-yl)imidazo[1,2-b]pyridazin-6-yl]amino]-1-phenylethanol Chemical compound C1([C@H](O)CNC=2C=CC3=NC=C(N3N=2)C=2OC=3C=CN=C(C=3C=2)OC)=CC=CC=C1 REAUMEFIVWHGEV-QGZVFWFLSA-N 0.000 claims description 2
• FMZSPBSNIGWHLI-GFCCVEGCSA-N (2r)-3-[[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]amino]propane-1,2-diol Chemical compound C1=CC=C2OC(C3=CN=C4C=CC(=NN43)NC[C@@H](O)CO)=CC2=C1 FMZSPBSNIGWHLI-GFCCVEGCSA-N 0.000 claims description 2
• VIVRNAFMYBZDMK-UHFFFAOYSA-N 1-[3-[[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]amino]-2-hydroxypropyl]pyrrolidin-2-one Chemical compound C1=CC2=NC=C(C=3OC4=CC=CC=C4C=3)N2N=C1NCC(O)CN1CCCC1=O VIVRNAFMYBZDMK-UHFFFAOYSA-N 0.000 claims description 2
• WUPHEESAOBFQHE-UHFFFAOYSA-N 1-[[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]amino]-2-phenylpropan-2-ol Chemical compound C1=CC2=NC=C(C=3OC4=CC=CC=C4C=3)N2N=C1NCC(O)(C)C1=CC=CC=C1 WUPHEESAOBFQHE-UHFFFAOYSA-N 0.000 claims description 2
• ZDUTXKMGGQLSCI-UHFFFAOYSA-N 1-[[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]amino]-3,3-dimethylbutan-2-ol Chemical compound C1=CC=C2OC(C3=CN=C4C=CC(=NN43)NCC(O)C(C)(C)C)=CC2=C1 ZDUTXKMGGQLSCI-UHFFFAOYSA-N 0.000 claims description 2
• HVZWKUPNOMUBND-UHFFFAOYSA-N 1-[[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]amino]-3-methylbutan-2-ol Chemical compound C1=CC=C2OC(C3=CN=C4C=CC(=NN43)NCC(O)C(C)C)=CC2=C1 HVZWKUPNOMUBND-UHFFFAOYSA-N 0.000 claims description 2
• BRQIZZYMSMRQPW-UHFFFAOYSA-N 1-[[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]amino]-3-morpholin-4-ylpropan-2-ol Chemical compound C1=CC2=NC=C(C=3OC4=CC=CC=C4C=3)N2N=C1NCC(O)CN1CCOCC1 BRQIZZYMSMRQPW-UHFFFAOYSA-N 0.000 claims description 2
• GWCDIHMLXPHIJH-UHFFFAOYSA-N 1-[[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]amino]-3-piperidin-1-ylpropan-2-ol Chemical compound C1=CC2=NC=C(C=3OC4=CC=CC=C4C=3)N2N=C1NCC(O)CN1CCCCC1 GWCDIHMLXPHIJH-UHFFFAOYSA-N 0.000 claims description 2
• FXYSPNIUQLRBDR-UHFFFAOYSA-N 1-[[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]amino]-3-pyrrolidin-1-ylpropan-2-ol Chemical compound C1=CC2=NC=C(C=3OC4=CC=CC=C4C=3)N2N=C1NCC(O)CN1CCCC1 FXYSPNIUQLRBDR-UHFFFAOYSA-N 0.000 claims description 2
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• HODSRCMIWTUXOT-UHFFFAOYSA-N 1-[[3-(4-methoxyfuro[3,2-c]pyridin-2-yl)imidazo[1,2-b]pyridazin-6-yl]amino]butan-2-ol Chemical compound N1=CC=C2OC(C3=CN=C4C=CC(=NN43)NCC(O)CC)=CC2=C1OC HODSRCMIWTUXOT-UHFFFAOYSA-N 0.000 claims description 2
• YIBLWSBTKLZNDK-UHFFFAOYSA-N 1-amino-3-[[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]amino]propan-2-ol Chemical compound C1=CC=C2OC(C3=CN=C4C=CC(=NN43)NCC(O)CN)=CC2=C1 YIBLWSBTKLZNDK-UHFFFAOYSA-N 0.000 claims description 2
• OLRVMPNQOMVXSW-UHFFFAOYSA-N 1-cyclopropyl-2-[[3-(4-methoxyfuro[3,2-c]pyridin-2-yl)imidazo[1,2-b]pyridazin-6-yl]amino]ethanol Chemical compound C=1C=2C(OC)=NC=CC=2OC=1C(N1N=2)=CN=C1C=CC=2NCC(O)C1CC1 OLRVMPNQOMVXSW-UHFFFAOYSA-N 0.000 claims description 2
• OSGKFCOGCDQATF-UHFFFAOYSA-N 2-[[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]amino]-1-(4-fluorophenyl)ethanol Chemical compound C1=CC2=NC=C(C=3OC4=CC=CC=C4C=3)N2N=C1NCC(O)C1=CC=C(F)C=C1 OSGKFCOGCDQATF-UHFFFAOYSA-N 0.000 claims description 2
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