JP2014513704A5 - - Google Patents
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- Publication number
- JP2014513704A5 JP2014513704A5 JP2014510768A JP2014510768A JP2014513704A5 JP 2014513704 A5 JP2014513704 A5 JP 2014513704A5 JP 2014510768 A JP2014510768 A JP 2014510768A JP 2014510768 A JP2014510768 A JP 2014510768A JP 2014513704 A5 JP2014513704 A5 JP 2014513704A5
- Authority
- JP
- Japan
- Prior art keywords
- nhr
- group
- alkyl
- amino
- pyridazin
- 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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- 125000001424 substituent group Chemical group 0.000 claims description 111
- 125000000217 alkyl group Chemical group 0.000 claims description 93
- 125000005843 halogen group Chemical group 0.000 claims description 74
- 125000003118 aryl group Chemical group 0.000 claims description 71
- 150000001875 compounds Chemical class 0.000 claims description 64
- 125000003545 alkoxy group Chemical group 0.000 claims description 52
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 52
- 125000001072 heteroaryl group Chemical group 0.000 claims description 47
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 44
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 41
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 32
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 32
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 32
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 30
- 125000006584 (C3-C10) heterocycloalkyl group Chemical group 0.000 claims description 29
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 22
- 239000011780 sodium chloride Substances 0.000 claims description 22
- 239000012453 solvate Substances 0.000 claims description 22
- 150000001204 N-oxides Chemical class 0.000 claims description 21
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 11
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N iodine atom Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- 125000005246 nonafluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 claims description 4
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 4
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical group [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 4
- 206010028980 Neoplasm Diseases 0.000 claims 20
- 201000010099 disease Diseases 0.000 claims 8
- 206010027476 Metastasis Diseases 0.000 claims 6
- 230000024932 T cell mediated immunity Effects 0.000 claims 6
- 230000010261 cell growth Effects 0.000 claims 6
- 230000004663 cell proliferation Effects 0.000 claims 6
- 230000001413 cellular Effects 0.000 claims 6
- 230000028709 inflammatory response Effects 0.000 claims 6
- 230000004083 survival Effects 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 210000004369 Blood Anatomy 0.000 claims 4
- 239000008280 blood Substances 0.000 claims 4
- 208000000409 Breast Neoplasms Diseases 0.000 claims 3
- 206010006187 Breast cancer Diseases 0.000 claims 3
- DUUUNXBJKXZKMJ-UHFFFAOYSA-N 2-[[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]amino]-1-(oxan-4-yl)ethanol Chemical compound C1=CC2=NC=C(C=3OC4=CC=CC=C4C=3)N2N=C1NCC(O)C1CCOCC1 DUUUNXBJKXZKMJ-UHFFFAOYSA-N 0.000 claims 2
- JPWHSYJJZACBLR-UHFFFAOYSA-N 2-[[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]amino]-1-cyclopropylethanol Chemical compound C1=CC2=NC=C(C=3OC4=CC=CC=C4C=3)N2N=C1NCC(O)C1CC1 JPWHSYJJZACBLR-UHFFFAOYSA-N 0.000 claims 2
- 210000004556 Brain Anatomy 0.000 claims 2
- 208000003174 Brain Neoplasms Diseases 0.000 claims 2
- 206010024324 Leukaemias Diseases 0.000 claims 2
- 210000004072 Lung Anatomy 0.000 claims 2
- 206010025323 Lymphomas Diseases 0.000 claims 2
- 206010027465 Metastases to skin Diseases 0.000 claims 2
- 206010029098 Neoplasm skin Diseases 0.000 claims 2
- 206010025310 Other lymphomas Diseases 0.000 claims 2
- 210000002307 Prostate Anatomy 0.000 claims 2
- 208000007097 Urinary Bladder Neoplasm Diseases 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 201000011523 endocrine gland cancer Diseases 0.000 claims 2
- 230000002496 gastric Effects 0.000 claims 2
- 230000001404 mediated Effects 0.000 claims 2
- 201000003793 myelodysplastic syndrome Diseases 0.000 claims 2
- 230000037361 pathway Effects 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 230000000268 renotropic Effects 0.000 claims 2
- 201000004477 skin sarcoma Diseases 0.000 claims 2
- AEWCZIWKJPNHNP-SFHVURJKSA-N (1R)-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-SFHVURJKSA-N 0.000 claims 1
- RGXKEDZRUAEVNO-KRWDZBQOSA-N (1R)-2-[[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]amino]-1-pyridin-3-ylethanol Chemical compound C1([C@H](CNC2=NN3C(C=4OC5=CC=CC=C5C=4)=CN=C3C=C2)O)=CC=CN=C1 RGXKEDZRUAEVNO-KRWDZBQOSA-N 0.000 claims 1
- 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 1
- 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 1
- IWISQJRXUSVULY-LLVKDONJSA-N (2R)-2-[[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]amino]propan-1-ol Chemical compound C1=CC=C2OC(C3=CN=C4C=CC(=NN43)N[C@@H](CO)C)=CC2=C1 IWISQJRXUSVULY-LLVKDONJSA-N 0.000 claims 1
- 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 1
- DCPLJLUNNRCGLN-ZDUSSCGKSA-N (2S)-2-[[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]amino]butan-1-ol Chemical compound C1=CC=C2OC(C3=CN=C4C=CC(=NN43)N[C@H](CO)CC)=CC2=C1 DCPLJLUNNRCGLN-ZDUSSCGKSA-N 0.000 claims 1
- FMZSPBSNIGWHLI-LBPRGKRZSA-N (2S)-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-LBPRGKRZSA-N 0.000 claims 1
- -1 1-Benzofuran-2-yl Chemical group 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- TZLKXQJTRKXXGE-UHFFFAOYSA-N 1-[[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]amino]butan-2-ol Chemical compound C1=CC=C2OC(C3=CN=C4C=CC(=NN43)NCC(O)CC)=CC2=C1 TZLKXQJTRKXXGE-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- IFJZKHAGICVCEH-UHFFFAOYSA-N 2-[[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]amino]-1-cyclohexylethanol Chemical compound C1=CC2=NC=C(C=3OC4=CC=CC=C4C=3)N2N=C1NCC(O)C1CCCCC1 IFJZKHAGICVCEH-UHFFFAOYSA-N 0.000 claims 1
- ALSWKDGXOWKHNH-UHFFFAOYSA-N 2-[[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]amino]-1-pyridin-2-ylethanol Chemical compound C1=CC2=NC=C(C=3OC4=CC=CC=C4C=3)N2N=C1NCC(O)C1=CC=CC=N1 ALSWKDGXOWKHNH-UHFFFAOYSA-N 0.000 claims 1
- QCYKKKBDJMYMKY-UHFFFAOYSA-N 2-[[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]amino]ethanol Chemical compound C1=CC=C2OC(C3=CN=C4C=CC(=NN43)NCCO)=CC2=C1 QCYKKKBDJMYMKY-UHFFFAOYSA-N 0.000 claims 1
- IWISQJRXUSVULY-UHFFFAOYSA-N 2-[[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]amino]propan-1-ol Chemical compound C1=CC=C2OC(C3=CN=C4C=CC(=NN43)NC(CO)C)=CC2=C1 IWISQJRXUSVULY-UHFFFAOYSA-N 0.000 claims 1
- PLFZEAHFYFOFAU-UHFFFAOYSA-N 2-[[3-(4-methoxyfuro[3,2-c]pyridin-2-yl)imidazo[1,2-b]pyridazin-6-yl]amino]-1-(oxan-4-yl)ethanol Chemical compound C=1C=2C(OC)=NC=CC=2OC=1C(N1N=2)=CN=C1C=CC=2NCC(O)C1CCOCC1 PLFZEAHFYFOFAU-UHFFFAOYSA-N 0.000 claims 1
- MHYZDKRZYATREZ-UHFFFAOYSA-N 3-[[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]amino]propan-1-ol Chemical compound C1=CC=C2OC(C3=CN=C4C=CC(=NN43)NCCCO)=CC2=C1 MHYZDKRZYATREZ-UHFFFAOYSA-N 0.000 claims 1
- FMZSPBSNIGWHLI-UHFFFAOYSA-N 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)NCC(O)CO)=CC2=C1 FMZSPBSNIGWHLI-UHFFFAOYSA-N 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- REAUMEFIVWHGEV-KRWDZBQOSA-N C1([C@@H](O)CNC=2C=CC3=NC=C(N3N=2)C=2OC=3C=CN=C(C=3C=2)OC)=CC=CC=C1 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 1
- KWMJEVFRHBAIFX-UHFFFAOYSA-N CC(C)(CO)CNC1=NN2C(C=C1)=NC=C2C1=CC2=C(O1)C=CC=C2 Chemical compound CC(C)(CO)CNC1=NN2C(C=C1)=NC=C2C1=CC2=C(O1)C=CC=C2 KWMJEVFRHBAIFX-UHFFFAOYSA-N 0.000 claims 1
- BXRRLRQODYQGEO-UHFFFAOYSA-N CC(O)CCNC1=NN2C(C=C1)=NC=C2C1=CC2=C(O1)C=CC=C2 Chemical compound CC(O)CCNC1=NN2C(C=C1)=NC=C2C1=CC2=C(O1)C=CC=C2 BXRRLRQODYQGEO-UHFFFAOYSA-N 0.000 claims 1
- VQJDTFPJDFMKNW-UHFFFAOYSA-N CCCCC(CO)NC1=NN2C(C=C1)=NC=C2C1=CC2=C(O1)C=CC=C2 Chemical compound CCCCC(CO)NC1=NN2C(C=C1)=NC=C2C1=CC2=C(O1)C=CC=C2 VQJDTFPJDFMKNW-UHFFFAOYSA-N 0.000 claims 1
- GQBQUHIYUGPPAX-LLVKDONJSA-N C[C@@H](O)CNC1=NN2C(C=C1)=NC=C2C1=CC2=C(O1)C=CC=C2 Chemical compound C[C@@H](O)CNC1=NN2C(C=C1)=NC=C2C1=CC2=C(O1)C=CC=C2 GQBQUHIYUGPPAX-LLVKDONJSA-N 0.000 claims 1
- GQBQUHIYUGPPAX-NSHDSACASA-N C[C@H](O)CNC1=NN2C(C=C1)=NC=C2C1=CC2=C(O1)C=CC=C2 Chemical compound C[C@H](O)CNC1=NN2C(C=C1)=NC=C2C1=CC2=C(O1)C=CC=C2 GQBQUHIYUGPPAX-NSHDSACASA-N 0.000 claims 1
- SBQAUBVLQRGQPC-UHFFFAOYSA-N OCC(CO)NC1=NN2C(C=C1)=NC=C2C1=CC2=C(O1)C=CC=C2 Chemical compound OCC(CO)NC1=NN2C(C=C1)=NC=C2C1=CC2=C(O1)C=CC=C2 SBQAUBVLQRGQPC-UHFFFAOYSA-N 0.000 claims 1
- HPIBHPKOFWESRC-SFHVURJKSA-N OC[C@H](CC1=CC=CC=C1)NC1=NN2C(C=C1)=NC=C2C1=CC2=C(O1)C=CC=C2 Chemical compound OC[C@H](CC1=CC=CC=C1)NC1=NN2C(C=C1)=NC=C2C1=CC2=C(O1)C=CC=C2 HPIBHPKOFWESRC-SFHVURJKSA-N 0.000 claims 1
- XXOAIQJDMSTOLB-SFHVURJKSA-N OC[C@H](CC1=CNC2=C1C=CC=C2)NC1=NN2C(C=C1)=NC=C2C1=CC2=C(O1)C=CC=C2 Chemical compound OC[C@H](CC1=CNC2=C1C=CC=C2)NC1=NN2C(C=C1)=NC=C2C1=CC2=C(O1)C=CC=C2 XXOAIQJDMSTOLB-SFHVURJKSA-N 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 230000000973 chemotherapeutic Effects 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- 230000004048 modification Effects 0.000 description 2
- 238000006011 modification reaction Methods 0.000 description 2
- 0 *C(*1)=C(*)C=C2*1C([N+]*)=C*2 Chemical compound *C(*1)=C(*)C=C2*1C([N+]*)=C*2 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11166426 | 2011-05-17 | ||
| EP11166426.4 | 2011-05-17 | ||
| PCT/EP2012/058931 WO2012156367A1 (en) | 2011-05-17 | 2012-05-14 | Amino-substituted imidazopyridazines as mknk1 kinase inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014513704A JP2014513704A (ja) | 2014-06-05 |
| JP2014513704A5 true JP2014513704A5 (US07943609-20110517-C00101.png) | 2017-02-09 |
| JP6121991B2 JP6121991B2 (ja) | 2017-04-26 |
Family
ID=46124340
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014510768A Active JP6121991B2 (ja) | 2011-05-17 | 2012-05-14 | 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 |
Country Status (6)
Families Citing this family (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103717604B (zh) | 2011-06-01 | 2016-06-01 | 拜耳知识产权有限责任公司 | 取代的氨基咪唑并哒嗪 |
| UA117092C2 (uk) | 2011-09-06 | 2018-06-25 | Байєр Інтеллектуал Проперті Гмбх | Амінозаміщені імідазопіридазини |
| US9320737B2 (en) * | 2011-09-23 | 2016-04-26 | Bayer Intellectual Property Gmbh | Substituted imidazopyridazines |
| WO2013087581A1 (en) * | 2011-12-12 | 2013-06-20 | Bayer Intellectual Property Gmbh | Amino-substituted imidazopyridazines |
| EP2858993B1 (en) | 2012-03-29 | 2018-01-10 | Bayer Intellectual Property GmbH | Amino-substituted imidazopyridazines |
| WO2013149909A1 (en) | 2012-04-04 | 2013-10-10 | Bayer Pharma Aktiengesellschaft | Amino-substituted imidazopyridazines |
| PT3495367T (pt) | 2012-06-13 | 2020-11-12 | Incyte Holdings Corp | Compostos tricíclicos substituídos como inibidores de fgfr |
| JP2015537017A (ja) * | 2012-11-19 | 2015-12-24 | バイエル ファーマ アクチエンゲゼルシャフト | アミノイミダゾピリダジン類 |
| JP6510419B2 (ja) * | 2012-12-17 | 2019-05-08 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | 液晶ディスプレイ、およびホメオトロピック配列を有する液晶媒体 |
| JP6437452B2 (ja) | 2013-01-14 | 2018-12-12 | インサイト・ホールディングス・コーポレイションＩｎｃｙｔｅ Ｈｏｌｄｉｎｇｓ Ｃｏｒｐｏｒａｔｉｏｎ | Ｐｉｍキナーゼ阻害剤として有用な二環式芳香族カルボキサミド化合物 |
| NZ710079A (en) | 2013-01-15 | 2020-01-31 | Incyte Holdings Corp | Thiazolecarboxamides and pyridinecarboxamide compounds useful as pim kinase inhibitors |
| CA2899352A1 (en) * | 2013-01-30 | 2014-08-07 | Bayer Pharma Aktiengesellschaft | Amidoimidazopyridazines as mknk-1 kinase inhibitors |
| WO2014118226A1 (en) * | 2013-02-01 | 2014-08-07 | Bayer Pharma Aktiengesellschaft | Substituted pyrazolopyrimidinylamino-indazoles |
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2012
- 2012-05-14 JP JP2014510768A patent/JP6121991B2/ja active Active
- 2012-05-14 CN CN201280035372.7A patent/CN103687858B/zh not_active Expired - Fee Related
- 2012-05-14 WO PCT/EP2012/058931 patent/WO2012156367A1/en active Application Filing
- 2012-05-14 US US14/118,519 patent/US20140288069A1/en not_active Abandoned
- 2012-05-14 EP EP12721826.1A patent/EP2710004A1/en not_active Withdrawn
- 2012-05-14 CA CA2836203A patent/CA2836203A1/en not_active Abandoned
