JP2009500348A5 - - Google Patents
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- JP2009500348A5 JP2009500348A5 JP2008519635A JP2008519635A JP2009500348A5 JP 2009500348 A5 JP2009500348 A5 JP 2009500348A5 JP 2008519635 A JP2008519635 A JP 2008519635A JP 2008519635 A JP2008519635 A JP 2008519635A JP 2009500348 A5 JP2009500348 A5 JP 2009500348A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- pyrimidin
- benzimidazol
- phenyl
- ylamino
- 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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- 150000001875 compounds Chemical class 0.000 claims description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- -1 cyano, hydroxy Chemical group 0.000 claims 76
- 125000000217 alkyl group Chemical group 0.000 claims 44
- 125000001475 halogen functional group Chemical group 0.000 claims 16
- 125000003545 alkoxy group Chemical group 0.000 claims 15
- 125000001072 heteroaryl group Chemical group 0.000 claims 14
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 14
- 239000001257 hydrogen Substances 0.000 claims 13
- 229910052739 hydrogen Inorganic materials 0.000 claims 13
- 150000003839 salts Chemical class 0.000 claims 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 10
- 108091000080 Phosphotransferase Proteins 0.000 claims 9
- 102000020233 phosphotransferase Human genes 0.000 claims 9
- 125000003118 aryl group Chemical group 0.000 claims 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 7
- 102100027842 Fibroblast growth factor receptor 3 Human genes 0.000 claims 6
- 101710182396 Fibroblast growth factor receptor 3 Proteins 0.000 claims 6
- 239000003795 chemical substances by application Substances 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- 125000004193 piperazinyl group Chemical group 0.000 claims 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- 125000001188 haloalkyl group Chemical group 0.000 claims 4
- 102100027907 Cytoplasmic tyrosine-protein kinase BMX Human genes 0.000 claims 3
- 101100481408 Danio rerio tie2 gene Proteins 0.000 claims 3
- 101100508533 Drosophila melanogaster IKKbeta gene Proteins 0.000 claims 3
- 101000742982 Homo sapiens Serine/threonine-protein kinase WNK3 Proteins 0.000 claims 3
- 101000997832 Homo sapiens Tyrosine-protein kinase JAK2 Proteins 0.000 claims 3
- 101000934996 Homo sapiens Tyrosine-protein kinase JAK3 Proteins 0.000 claims 3
- 101150028321 Lck gene Proteins 0.000 claims 3
- 101150003567 Mapk12 gene Proteins 0.000 claims 3
- 102000056243 Mitogen-activated protein kinase 12 Human genes 0.000 claims 3
- 108700015929 Mitogen-activated protein kinase 12 Proteins 0.000 claims 3
- 101100354317 Mus musculus Ptk6 gene Proteins 0.000 claims 3
- 101100481410 Mus musculus Tek gene Proteins 0.000 claims 3
- 101150056950 Ntrk2 gene Proteins 0.000 claims 3
- 108010029869 Proto-Oncogene Proteins c-raf Proteins 0.000 claims 3
- 102100033479 RAF proto-oncogene serine/threonine-protein kinase Human genes 0.000 claims 3
- 101150071831 RPS6KA1 gene Proteins 0.000 claims 3
- 101150105578 SAPK3 gene Proteins 0.000 claims 3
- 101150083487 SIK1 gene Proteins 0.000 claims 3
- 102000001332 SRC Human genes 0.000 claims 3
- 108060006706 SRC Proteins 0.000 claims 3
- 102100038115 Serine/threonine-protein kinase WNK3 Human genes 0.000 claims 3
- 102100031167 Tyrosine-protein kinase CSK Human genes 0.000 claims 3
- 102100033444 Tyrosine-protein kinase JAK2 Human genes 0.000 claims 3
- 102100025387 Tyrosine-protein kinase JAK3 Human genes 0.000 claims 3
- 108010053099 Vascular Endothelial Growth Factor Receptor-2 Proteins 0.000 claims 3
- 102100033177 Vascular endothelial growth factor receptor 2 Human genes 0.000 claims 3
- 239000004480 active ingredient Substances 0.000 claims 3
- 125000002947 alkylene group Chemical group 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 102000052116 epidermal growth factor receptor activity proteins Human genes 0.000 claims 3
- 108700015053 epidermal growth factor receptor activity proteins Proteins 0.000 claims 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 230000001404 mediated effect Effects 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 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 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims 3
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 2
- ZCHQKLBQZFZVBL-UHFFFAOYSA-N 2-[4-[2-methyl-6-[[6-[2-(2,4,6-trimethylanilino)benzimidazol-1-yl]pyrimidin-4-yl]amino]pyrimidin-4-yl]piperazin-1-yl]ethanol Chemical compound CC1=CC(C)=CC(C)=C1NC1=NC2=CC=CC=C2N1C1=CC(NC=2N=C(C)N=C(C=2)N2CCN(CCO)CC2)=NC=N1 ZCHQKLBQZFZVBL-UHFFFAOYSA-N 0.000 claims 2
- MABPYIPHMYIDIF-UHFFFAOYSA-N 3-[[1-(6-aminopyrimidin-4-yl)benzimidazol-2-yl]amino]-4-methyl-n-[4-(2-methylimidazol-1-yl)-3-(trifluoromethyl)phenyl]benzamide Chemical compound CC1=NC=CN1C(C(=C1)C(F)(F)F)=CC=C1NC(=O)C1=CC=C(C)C(NC=2N(C3=CC=CC=C3N=2)C=2N=CN=C(N)C=2)=C1 MABPYIPHMYIDIF-UHFFFAOYSA-N 0.000 claims 2
- OWWGCOSIPYTEIP-UHFFFAOYSA-N 3-[[3-[6-[4-(diethylamino)butylamino]pyrimidin-4-yl]imidazo[4,5-b]pyridin-2-yl]amino]-4-methyl-n-[3-(trifluoromethyl)phenyl]benzamide Chemical compound C1=NC(NCCCCN(CC)CC)=CC(N2C3=NC=CC=C3N=C2NC=2C(=CC=C(C=2)C(=O)NC=2C=C(C=CC=2)C(F)(F)F)C)=N1 OWWGCOSIPYTEIP-UHFFFAOYSA-N 0.000 claims 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 2
- 101100240519 Caenorhabditis elegans nhr-13 gene Proteins 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
- DLDALFWGOIAFRT-UHFFFAOYSA-N n-[3-[[1-(6-aminopyrimidin-4-yl)benzimidazol-2-yl]amino]-4-methylphenyl]-3-morpholin-4-yl-5-(trifluoromethyl)benzamide Chemical compound C1=C(NC=2N(C3=CC=CC=C3N=2)C=2N=CN=C(N)C=2)C(C)=CC=C1NC(=O)C(C=C(C=1)C(F)(F)F)=CC=1N1CCOCC1 DLDALFWGOIAFRT-UHFFFAOYSA-N 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 150000003254 radicals Chemical class 0.000 claims 2
- ZPRJXZVPSKFXMT-UHFFFAOYSA-N 1-(6-aminopyrimidin-4-yl)-n-(2,4,6-trimethylphenyl)benzimidazol-2-amine Chemical compound CC1=CC(C)=CC(C)=C1NC1=NC2=CC=CC=C2N1C1=CC(N)=NC=N1 ZPRJXZVPSKFXMT-UHFFFAOYSA-N 0.000 claims 1
- PGZPWMBGGPDJNU-UHFFFAOYSA-N 1-(6-aminopyrimidin-4-yl)-n-(2,5-dimethylphenyl)benzimidazol-2-amine Chemical compound CC1=CC=C(C)C(NC=2N(C3=CC=CC=C3N=2)C=2N=CN=C(N)C=2)=C1 PGZPWMBGGPDJNU-UHFFFAOYSA-N 0.000 claims 1
- AMXFBJCSYDYPNY-UHFFFAOYSA-N 1-(6-aminopyrimidin-4-yl)-n-(2-bromo-4,6-dimethylphenyl)benzimidazol-2-amine Chemical compound BrC1=CC(C)=CC(C)=C1NC1=NC2=CC=CC=C2N1C1=CC(N)=NC=N1 AMXFBJCSYDYPNY-UHFFFAOYSA-N 0.000 claims 1
- KCFYRZYFGXYNKV-UHFFFAOYSA-N 1-(6-aminopyrimidin-4-yl)-n-(2-chloro-6-methylphenyl)benzimidazol-2-amine Chemical compound CC1=CC=CC(Cl)=C1NC1=NC2=CC=CC=C2N1C1=CC(N)=NC=N1 KCFYRZYFGXYNKV-UHFFFAOYSA-N 0.000 claims 1
- MQDQPOHOVUJCRE-UHFFFAOYSA-N 1-(6-aminopyrimidin-4-yl)-n-(2-methyl-5-nitrophenyl)benzimidazol-2-amine Chemical compound CC1=CC=C([N+]([O-])=O)C=C1NC1=NC2=CC=CC=C2N1C1=CC(N)=NC=N1 MQDQPOHOVUJCRE-UHFFFAOYSA-N 0.000 claims 1
- LBBRKDXTUAPHJP-UHFFFAOYSA-N 1-(6-aminopyrimidin-4-yl)-n-(3,5-dichlorophenyl)benzimidazol-2-amine Chemical compound C1=NC(N)=CC(N2C3=CC=CC=C3N=C2NC=2C=C(Cl)C=C(Cl)C=2)=N1 LBBRKDXTUAPHJP-UHFFFAOYSA-N 0.000 claims 1
- KOSUSJHYYOWKIU-UHFFFAOYSA-N 1-(6-aminopyrimidin-4-yl)-n-(3-bromo-2,4,6-trimethylphenyl)benzimidazol-2-amine Chemical compound CC1=C(Br)C(C)=CC(C)=C1NC1=NC2=CC=CC=C2N1C1=CC(N)=NC=N1 KOSUSJHYYOWKIU-UHFFFAOYSA-N 0.000 claims 1
- MYHGRFHXVQNVTR-UHFFFAOYSA-N 1-(6-aminopyrimidin-4-yl)-n-(3-bromo-2-methylphenyl)benzimidazol-2-amine Chemical compound CC1=C(Br)C=CC=C1NC1=NC2=CC=CC=C2N1C1=CC(N)=NC=N1 MYHGRFHXVQNVTR-UHFFFAOYSA-N 0.000 claims 1
- IYPXINUXUQCPAS-UHFFFAOYSA-N 1-(6-aminopyrimidin-4-yl)-n-(4-bromo-2,6-dimethylphenyl)benzimidazol-2-amine Chemical compound CC1=CC(Br)=CC(C)=C1NC1=NC2=CC=CC=C2N1C1=CC(N)=NC=N1 IYPXINUXUQCPAS-UHFFFAOYSA-N 0.000 claims 1
- KNONMQQQOBYVOQ-UHFFFAOYSA-N 1-(6-aminopyrimidin-4-yl)-n-(4-bromo-2-chloro-6-methylphenyl)benzimidazol-2-amine Chemical compound CC1=CC(Br)=CC(Cl)=C1NC1=NC2=CC=CC=C2N1C1=CC(N)=NC=N1 KNONMQQQOBYVOQ-UHFFFAOYSA-N 0.000 claims 1
- VICXLLUFBVZJII-UHFFFAOYSA-N 1-(6-aminopyrimidin-4-yl)-n-(4-bromo-2-methylphenyl)benzimidazol-2-amine Chemical compound CC1=CC(Br)=CC=C1NC1=NC2=CC=CC=C2N1C1=CC(N)=NC=N1 VICXLLUFBVZJII-UHFFFAOYSA-N 0.000 claims 1
- QMEQGSHLHUBJAH-UHFFFAOYSA-N 1-(6-aminopyrimidin-4-yl)-n-(4-phenoxyphenyl)benzimidazol-2-amine Chemical compound C1=NC(N)=CC(N2C3=CC=CC=C3N=C2NC=2C=CC(OC=3C=CC=CC=3)=CC=2)=N1 QMEQGSHLHUBJAH-UHFFFAOYSA-N 0.000 claims 1
- XCCPEQBWSKUFKT-UHFFFAOYSA-N 1-(6-aminopyrimidin-4-yl)-n-(4-tert-butylphenyl)benzimidazol-2-amine Chemical compound C1=CC(C(C)(C)C)=CC=C1NC1=NC2=CC=CC=C2N1C1=CC(N)=NC=N1 XCCPEQBWSKUFKT-UHFFFAOYSA-N 0.000 claims 1
- HBLYSHKOSXRZSF-UHFFFAOYSA-N 1-(6-aminopyrimidin-4-yl)-n-(5-bromo-2-methylphenyl)benzimidazol-2-amine Chemical compound CC1=CC=C(Br)C=C1NC1=NC2=CC=CC=C2N1C1=CC(N)=NC=N1 HBLYSHKOSXRZSF-UHFFFAOYSA-N 0.000 claims 1
- CZTBVXSLJFITNQ-UHFFFAOYSA-N 1-(6-aminopyrimidin-4-yl)-n-[2-(trifluoromethoxy)phenyl]benzimidazol-2-amine Chemical compound C1=NC(N)=CC(N2C3=CC=CC=C3N=C2NC=2C(=CC=CC=2)OC(F)(F)F)=N1 CZTBVXSLJFITNQ-UHFFFAOYSA-N 0.000 claims 1
- RUHHGFDMDPJXBK-UHFFFAOYSA-N 1-pyrimidin-4-yl-n-[2-(trifluoromethoxy)phenyl]benzimidazol-2-amine Chemical compound FC(F)(F)OC1=CC=CC=C1NC1=NC2=CC=CC=C2N1C1=CC=NC=N1 RUHHGFDMDPJXBK-UHFFFAOYSA-N 0.000 claims 1
- JPBNPEUKQQCSCS-UHFFFAOYSA-N 2,5-dimethoxy-n-methyl-3-[[1-[6-(4-morpholin-4-ylanilino)pyrimidin-4-yl]benzimidazol-2-yl]amino]benzamide Chemical compound CNC(=O)C1=CC(OC)=CC(NC=2N(C3=CC=CC=C3N=2)C=2N=CN=C(NC=3C=CC(=CC=3)N3CCOCC3)C=2)=C1OC JPBNPEUKQQCSCS-UHFFFAOYSA-N 0.000 claims 1
- ZIDIYMNYXUIOMW-UHFFFAOYSA-N 2,5-dimethyl-n-[4-methyl-3-[(1-pyrimidin-4-ylbenzimidazol-2-yl)amino]phenyl]pyrazole-3-carboxamide Chemical compound CN1N=C(C)C=C1C(=O)NC1=CC=C(C)C(NC=2N(C3=CC=CC=C3N=2)C=2N=CN=CC=2)=C1 ZIDIYMNYXUIOMW-UHFFFAOYSA-N 0.000 claims 1
- PAOFCZHAUIKUDF-UHFFFAOYSA-N 2-[4-[6-[[6-(2-chlorobenzimidazol-1-yl)pyrimidin-4-yl]amino]-2-methylpyrimidin-4-yl]piperazin-1-yl]ethanol Chemical compound N=1C(C)=NC(NC=2N=CN=C(C=2)N2C3=CC=CC=C3N=C2Cl)=CC=1N1CCN(CCO)CC1 PAOFCZHAUIKUDF-UHFFFAOYSA-N 0.000 claims 1
- ZFGRQAXIHZXQBZ-UHFFFAOYSA-N 2-[4-[6-[[6-[2-(2-chloro-6-methylanilino)benzimidazol-1-yl]pyrimidin-4-yl]amino]-2-methylpyrimidin-4-yl]piperazin-1-yl]ethanol Chemical compound C=1C(N2CCN(CCO)CC2)=NC(C)=NC=1NC(N=CN=1)=CC=1N(C1=CC=CC=C1N=1)C=1NC1=C(C)C=CC=C1Cl ZFGRQAXIHZXQBZ-UHFFFAOYSA-N 0.000 claims 1
- GHYRZLPYEITFBH-UHFFFAOYSA-N 2-[4-[6-[[6-[2-(3-chloro-2,6-dimethylanilino)benzimidazol-1-yl]pyrimidin-4-yl]amino]-2-methylpyrimidin-4-yl]piperazin-1-yl]ethanol Chemical compound C=1C(N2CCN(CCO)CC2)=NC(C)=NC=1NC(N=CN=1)=CC=1N(C1=CC=CC=C1N=1)C=1NC1=C(C)C=CC(Cl)=C1C GHYRZLPYEITFBH-UHFFFAOYSA-N 0.000 claims 1
- AKGZCBJCSSQLLS-UHFFFAOYSA-N 2-[4-[6-[[6-[2-(4-bromo-2-methylanilino)benzimidazol-1-yl]pyrimidin-4-yl]amino]-2-methylpyrimidin-4-yl]piperazin-1-yl]ethanol Chemical compound C=1C(N2CCN(CCO)CC2)=NC(C)=NC=1NC(N=CN=1)=CC=1N(C1=CC=CC=C1N=1)C=1NC1=CC=C(Br)C=C1C AKGZCBJCSSQLLS-UHFFFAOYSA-N 0.000 claims 1
- GTBRMMWAOBROMF-UHFFFAOYSA-N 2-[4-[6-[[6-[2-(5-methoxy-2-methylanilino)benzimidazol-1-yl]pyrimidin-4-yl]amino]-2-methylpyrimidin-4-yl]piperazin-1-yl]ethanol Chemical compound COC1=CC=C(C)C(NC=2N(C3=CC=CC=C3N=2)C=2N=CN=C(NC=3N=C(C)N=C(C=3)N3CCN(CCO)CC3)C=2)=C1 GTBRMMWAOBROMF-UHFFFAOYSA-N 0.000 claims 1
- NAFRBGSOGMFGPE-UHFFFAOYSA-N 2-tert-butyl-n-[4-methyl-3-[(1-pyrimidin-4-ylbenzimidazol-2-yl)amino]phenyl]pyridine-4-carboxamide Chemical compound C1=C(NC=2N(C3=CC=CC=C3N=2)C=2N=CN=CC=2)C(C)=CC=C1NC(=O)C1=CC=NC(C(C)(C)C)=C1 NAFRBGSOGMFGPE-UHFFFAOYSA-N 0.000 claims 1
- HUEUNRUAWYBCTL-UHFFFAOYSA-N 3-(1-methylpiperidin-4-yl)oxy-n-[4-methyl-3-[(1-pyrimidin-4-ylbenzimidazol-2-yl)amino]phenyl]-5-(trifluoromethyl)benzamide Chemical compound C1CN(C)CCC1OC1=CC(C(=O)NC=2C=C(NC=3N(C4=CC=CC=C4N=3)C=3N=CN=CC=3)C(C)=CC=2)=CC(C(F)(F)F)=C1 HUEUNRUAWYBCTL-UHFFFAOYSA-N 0.000 claims 1
- HLZLAQGJKOZBRL-UHFFFAOYSA-N 3-(4-ethylpiperazin-1-yl)-n-[4-methyl-3-[(1-pyrimidin-4-ylbenzimidazol-2-yl)amino]phenyl]-5-(trifluoromethyl)benzamide Chemical compound C1CN(CC)CCN1C1=CC(C(=O)NC=2C=C(NC=3N(C4=CC=CC=C4N=3)C=3N=CN=CC=3)C(C)=CC=2)=CC(C(F)(F)F)=C1 HLZLAQGJKOZBRL-UHFFFAOYSA-N 0.000 claims 1
- VSMPOKKWINPFAX-UHFFFAOYSA-N 3-(4-methylimidazol-1-yl)-n-[4-methyl-3-[(1-pyrimidin-4-ylbenzimidazol-2-yl)amino]phenyl]-5-(trifluoromethyl)benzamide Chemical compound C1=NC(C)=CN1C1=CC(C(=O)NC=2C=C(NC=3N(C4=CC=CC=C4N=3)C=3N=CN=CC=3)C(C)=CC=2)=CC(C(F)(F)F)=C1 VSMPOKKWINPFAX-UHFFFAOYSA-N 0.000 claims 1
- DQDDAVDAKOJGAJ-UHFFFAOYSA-N 3-(4-methylpiperazin-1-yl)-n-[4-methyl-3-[(1-pyrimidin-4-ylbenzimidazol-2-yl)amino]phenyl]-5-(trifluoromethyl)benzamide Chemical compound C1CN(C)CCN1C1=CC(C(=O)NC=2C=C(NC=3N(C4=CC=CC=C4N=3)C=3N=CN=CC=3)C(C)=CC=2)=CC(C(F)(F)F)=C1 DQDDAVDAKOJGAJ-UHFFFAOYSA-N 0.000 claims 1
- XWTZPPPOJTYYGH-UHFFFAOYSA-N 3-[4-(2-hydroxyethyl)piperazin-1-yl]-n-[4-methyl-3-[(1-pyrimidin-4-ylbenzimidazol-2-yl)amino]phenyl]-5-(trifluoromethyl)benzamide Chemical compound C1=C(NC=2N(C3=CC=CC=C3N=2)C=2N=CN=CC=2)C(C)=CC=C1NC(=O)C(C=C(C=1)C(F)(F)F)=CC=1N1CCN(CCO)CC1 XWTZPPPOJTYYGH-UHFFFAOYSA-N 0.000 claims 1
- CYTADLUJFNFLQB-UHFFFAOYSA-N 3-[[1-(6-aminopyrimidin-4-yl)benzimidazol-2-yl]amino]-2,5-dimethoxy-n-methylbenzamide Chemical compound CNC(=O)C1=CC(OC)=CC(NC=2N(C3=CC=CC=C3N=2)C=2N=CN=C(N)C=2)=C1OC CYTADLUJFNFLQB-UHFFFAOYSA-N 0.000 claims 1
- NHVGQRASKRTWLZ-UHFFFAOYSA-N 3-[[1-(6-aminopyrimidin-4-yl)benzimidazol-2-yl]amino]-4-methyl-n-[3-(4-methylimidazol-1-yl)-5-(trifluoromethyl)phenyl]benzamide Chemical compound C1=NC(C)=CN1C1=CC(NC(=O)C=2C=C(NC=3N(C4=CC=CC=C4N=3)C=3N=CN=C(N)C=3)C(C)=CC=2)=CC(C(F)(F)F)=C1 NHVGQRASKRTWLZ-UHFFFAOYSA-N 0.000 claims 1
- LAXDODUPLVBDLC-UHFFFAOYSA-N 3-[[1-(6-aminopyrimidin-4-yl)benzimidazol-2-yl]amino]-4-methyl-n-[3-(trifluoromethyl)phenyl]benzamide Chemical compound CC1=CC=C(C(=O)NC=2C=C(C=CC=2)C(F)(F)F)C=C1NC1=NC2=CC=CC=C2N1C1=CC(N)=NC=N1 LAXDODUPLVBDLC-UHFFFAOYSA-N 0.000 claims 1
- OJANARVSPGQGCL-UHFFFAOYSA-N 3-[[1-(6-aminopyrimidin-4-yl)benzimidazol-2-yl]amino]-4-methylbenzoic acid Chemical compound CC1=CC=C(C(O)=O)C=C1NC1=NC2=CC=CC=C2N1C1=CC(N)=NC=N1 OJANARVSPGQGCL-UHFFFAOYSA-N 0.000 claims 1
- QZMDXHOIKJAUND-UHFFFAOYSA-N 3-[[1-(6-aminopyrimidin-4-yl)benzimidazol-2-yl]amino]-5-methoxy-n-[3-(trifluoromethyl)phenyl]benzamide Chemical compound C=1C(C(=O)NC=2C=C(C=CC=2)C(F)(F)F)=CC(OC)=CC=1NC1=NC2=CC=CC=C2N1C1=CC(N)=NC=N1 QZMDXHOIKJAUND-UHFFFAOYSA-N 0.000 claims 1
- PFIQMKZHLWNUCL-UHFFFAOYSA-N 3-[[1-(6-aminopyrimidin-4-yl)benzimidazol-2-yl]amino]-n-[4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]-4-methylbenzamide Chemical compound C1CN(CC)CCN1CC(C(=C1)C(F)(F)F)=CC=C1NC(=O)C1=CC=C(C)C(NC=2N(C3=CC=CC=C3N=2)C=2N=CN=C(N)C=2)=C1 PFIQMKZHLWNUCL-UHFFFAOYSA-N 0.000 claims 1
- AGYCTUZXJHRHMX-UHFFFAOYSA-N 3-n-[1-(6-aminopyrimidin-4-yl)benzimidazol-2-yl]-4-methylbenzene-1,3-diamine Chemical compound CC1=CC=C(N)C=C1NC1=NC2=CC=CC=C2N1C1=CC(N)=NC=N1 AGYCTUZXJHRHMX-UHFFFAOYSA-N 0.000 claims 1
- NQYGSGQCRJPLIU-UHFFFAOYSA-N 4-methyl-3-n-(1-pyrimidin-4-ylbenzimidazol-2-yl)benzene-1,3-diamine Chemical compound CC1=CC=C(N)C=C1NC1=NC2=CC=CC=C2N1C1=CC=NC=N1 NQYGSGQCRJPLIU-UHFFFAOYSA-N 0.000 claims 1
- SQUDMCTZEYADTE-UHFFFAOYSA-N 4-n-[6-[2-(2-chloro-6-methylanilino)benzimidazol-1-yl]pyrimidin-4-yl]-2-methyl-6-n-(2-morpholin-4-ylethyl)pyrimidine-4,6-diamine Chemical compound C=1C(NC=2N=CN=C(C=2)N2C3=CC=CC=C3N=C2NC=2C(=CC=CC=2C)Cl)=NC(C)=NC=1NCCN1CCOCC1 SQUDMCTZEYADTE-UHFFFAOYSA-N 0.000 claims 1
- YBWMFEGKCNSVBL-UHFFFAOYSA-N 4-n-[6-[2-(2-chloro-6-methylanilino)benzimidazol-1-yl]pyrimidin-4-yl]-5-methyl-6-n-(2-morpholin-4-ylethyl)pyrimidine-4,6-diamine Chemical compound CC1=CC=CC(Cl)=C1NC1=NC2=CC=CC=C2N1C1=CC(NC=2C(=C(NCCN3CCOCC3)N=CN=2)C)=NC=N1 YBWMFEGKCNSVBL-UHFFFAOYSA-N 0.000 claims 1
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- QGDUBFDIQPISBZ-UHFFFAOYSA-N n-[4-methyl-3-[(1-pyrimidin-4-ylbenzimidazol-2-yl)amino]phenyl]-3-(piperidin-4-ylamino)-5-(trifluoromethyl)benzamide Chemical compound C1=C(NC=2N(C3=CC=CC=C3N=2)C=2N=CN=CC=2)C(C)=CC=C1NC(=O)C(C=C(C=1)C(F)(F)F)=CC=1NC1CCNCC1 QGDUBFDIQPISBZ-UHFFFAOYSA-N 0.000 claims 1
- XZGBSCJUAQDTBL-UHFFFAOYSA-N n-[4-methyl-3-[(1-pyrimidin-4-ylbenzimidazol-2-yl)amino]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(NC=2N(C3=CC=CC=C3N=2)C=2N=CN=CC=2)C(C)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 XZGBSCJUAQDTBL-UHFFFAOYSA-N 0.000 claims 1
- NNLIMNLYBCBYQJ-UHFFFAOYSA-N n-[4-methyl-3-[(1-pyrimidin-4-ylbenzimidazol-2-yl)amino]phenyl]-3-piperazin-1-yl-5-(trifluoromethyl)benzamide Chemical compound C1=C(NC=2N(C3=CC=CC=C3N=2)C=2N=CN=CC=2)C(C)=CC=C1NC(=O)C(C=C(C=1)C(F)(F)F)=CC=1N1CCNCC1 NNLIMNLYBCBYQJ-UHFFFAOYSA-N 0.000 claims 1
- XHZSFDNNTPIEDH-UHFFFAOYSA-N n-[4-methyl-3-[(1-pyrimidin-4-ylbenzimidazol-2-yl)amino]phenyl]-3-piperidin-4-yloxy-5-(trifluoromethyl)benzamide Chemical compound C1=C(NC=2N(C3=CC=CC=C3N=2)C=2N=CN=CC=2)C(C)=CC=C1NC(=O)C(C=C(C=1)C(F)(F)F)=CC=1OC1CCNCC1 XHZSFDNNTPIEDH-UHFFFAOYSA-N 0.000 claims 1
- JQAVGDHDTJHEOD-UHFFFAOYSA-N n-[4-methyl-3-[(1-pyrimidin-4-ylbenzimidazol-2-yl)amino]phenyl]-3-pyrrolidin-2-yloxy-5-(trifluoromethyl)benzamide Chemical compound C1=C(NC=2N(C3=CC=CC=C3N=2)C=2N=CN=CC=2)C(C)=CC=C1NC(=O)C(C=C(C=1)C(F)(F)F)=CC=1OC1CCCN1 JQAVGDHDTJHEOD-UHFFFAOYSA-N 0.000 claims 1
- YBQBSRIBXPKWKC-UHFFFAOYSA-N n-[4-methyl-3-[[1-(1h-pyrazolo[3,4-d]pyrimidin-4-yl)benzimidazol-2-yl]amino]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(NC=2N(C3=CC=CC=C3N=2)C=2C=3C=NNC=3N=CN=2)C(C)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 YBQBSRIBXPKWKC-UHFFFAOYSA-N 0.000 claims 1
- GGEALBVZDVXUND-UHFFFAOYSA-N n-[4-methyl-3-[[1-(6-morpholin-4-ylpyrimidin-4-yl)benzimidazol-2-yl]amino]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(NC=2N(C3=CC=CC=C3N=2)C=2N=CN=C(C=2)N2CCOCC2)C(C)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 GGEALBVZDVXUND-UHFFFAOYSA-N 0.000 claims 1
- QNTVHKHUPBDBQF-UHFFFAOYSA-N n-[4-methyl-3-[[1-[5-methyl-6-[2-(4-methylpiperazin-1-yl)ethylamino]pyrimidin-4-yl]benzimidazol-2-yl]amino]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1CN(C)CCN1CCNC1=NC=NC(N2C3=CC=CC=C3N=C2NC=2C(=CC=C(NC(=O)C=3C=C(C=CC=3)C(F)(F)F)C=2)C)=C1C QNTVHKHUPBDBQF-UHFFFAOYSA-N 0.000 claims 1
- CIIHDSYJQQIKAC-UHFFFAOYSA-N n-[4-methyl-3-[[1-[5-methyl-6-[3-(4-methylpiperazin-1-yl)propylamino]pyrimidin-4-yl]benzimidazol-2-yl]amino]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1CN(C)CCN1CCCNC1=NC=NC(N2C3=CC=CC=C3N=C2NC=2C(=CC=C(NC(=O)C=3C=C(C=CC=3)C(F)(F)F)C=2)C)=C1C CIIHDSYJQQIKAC-UHFFFAOYSA-N 0.000 claims 1
- GLYDCPPHXDVIKA-UHFFFAOYSA-N n-[4-methyl-3-[[1-[6-(2-pyridin-2-ylethylamino)pyrimidin-4-yl]benzimidazol-2-yl]amino]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(NC=2N(C3=CC=CC=C3N=2)C=2N=CN=C(NCCC=3N=CC=CC=3)C=2)C(C)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 GLYDCPPHXDVIKA-UHFFFAOYSA-N 0.000 claims 1
- SLGMHHPVSAPRLI-UHFFFAOYSA-N n-[4-methyl-3-[[1-[6-(2-pyrrolidin-1-ylethylamino)pyrimidin-4-yl]benzimidazol-2-yl]amino]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(NC=2N(C3=CC=CC=C3N=2)C=2N=CN=C(NCCN3CCCC3)C=2)C(C)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 SLGMHHPVSAPRLI-UHFFFAOYSA-N 0.000 claims 1
- UOJGMLQOPYVDAD-UHFFFAOYSA-N n-[4-methyl-3-[[1-[6-(3-morpholin-4-ylpropylamino)pyrimidin-4-yl]benzimidazol-2-yl]amino]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(NC=2N(C3=CC=CC=C3N=2)C=2N=CN=C(NCCCN3CCOCC3)C=2)C(C)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 UOJGMLQOPYVDAD-UHFFFAOYSA-N 0.000 claims 1
- QQVLIPDYPZXRET-UHFFFAOYSA-N n-[4-methyl-3-[[1-[6-[(1-methylpiperidin-4-yl)amino]pyrimidin-4-yl]benzimidazol-2-yl]amino]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1CN(C)CCC1NC1=CC(N2C3=CC=CC=C3N=C2NC=2C(=CC=C(NC(=O)C=3C=C(C=CC=3)C(F)(F)F)C=2)C)=NC=N1 QQVLIPDYPZXRET-UHFFFAOYSA-N 0.000 claims 1
- XAWZDGHYUZKTTO-UHFFFAOYSA-N n-[4-methyl-3-[[1-[6-[(4-methylpiperazin-1-yl)amino]pyrimidin-4-yl]benzimidazol-2-yl]amino]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1CN(C)CCN1NC1=CC(N2C3=CC=CC=C3N=C2NC=2C(=CC=C(NC(=O)C=3C=C(C=CC=3)C(F)(F)F)C=2)C)=NC=N1 XAWZDGHYUZKTTO-UHFFFAOYSA-N 0.000 claims 1
- DUSWCXDALWVDSK-UHFFFAOYSA-N n-[4-methyl-3-[[1-[6-[2-(4-methylpiperazin-1-yl)ethylamino]pyrimidin-4-yl]benzimidazol-2-yl]amino]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1CN(C)CCN1CCNC1=CC(N2C3=CC=CC=C3N=C2NC=2C(=CC=C(NC(=O)C=3C=C(C=CC=3)C(F)(F)F)C=2)C)=NC=N1 DUSWCXDALWVDSK-UHFFFAOYSA-N 0.000 claims 1
- FILQIUCXPQZUON-UHFFFAOYSA-N n-[4-methyl-3-[[1-[6-[3-(4-methylpiperazin-1-yl)propylamino]pyrimidin-4-yl]benzimidazol-2-yl]amino]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1CN(C)CCN1CCCNC1=CC(N2C3=CC=CC=C3N=C2NC=2C(=CC=C(NC(=O)C=3C=C(C=CC=3)C(F)(F)F)C=2)C)=NC=N1 FILQIUCXPQZUON-UHFFFAOYSA-N 0.000 claims 1
- XJMUUEMSIJHHBF-UHFFFAOYSA-N n-[6-[2-(2-chloro-6-methylanilino)benzimidazol-1-yl]pyrimidin-4-yl]morpholin-4-amine Chemical compound CC1=CC=CC(Cl)=C1NC1=NC2=CC=CC=C2N1C1=CC(NN2CCOCC2)=NC=N1 XJMUUEMSIJHHBF-UHFFFAOYSA-N 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000006513 pyridinyl methyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000005302 thiazolylmethyl group Chemical group [H]C1=C([H])N=C(S1)C([H])([H])* 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 238000002054 transplantation Methods 0.000 description 2
- 206010006448 Bronchiolitis Diseases 0.000 description 1
- 0 C*C*C=*CN* Chemical compound C*C*C=*CN* 0.000 description 1
- 230000000735 allogeneic effect Effects 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 230000000414 obstructive effect Effects 0.000 description 1
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Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
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| DE602004009295T2 (de) | 2003-01-14 | 2008-07-03 | Arena Pharmaceuticals, Inc., San Diego | 1,2,3-trisubstituierte aryl- und heteroarylderivate als modulatoren des metabolismus zur vorbeugung und behandlung von metabolismus-bedingten krankheiten wie diabetes oder hyperglykämie |
| AR045047A1 (es) * | 2003-07-11 | 2005-10-12 | Arena Pharm Inc | Derivados arilo y heteroarilo trisustituidos como moduladores del metabolismo y de la profilaxis y tratamiento de desordenes relacionados con los mismos |
| EP2292620A3 (en) | 2003-07-14 | 2011-06-22 | Arena Pharmaceuticals, Inc. | Fused-aryl and heteroaryl derivatives as modulators of metabolism and the prohylaxis and treatment of disorders related thereto |
| MY148521A (en) | 2005-01-10 | 2013-04-30 | Arena Pharm Inc | Substituted pyridinyl and pyrimidinyl derivatives as modulators of metabolism and the treatment of disorders related thereto |
| MX2009002046A (es) | 2006-08-24 | 2009-03-06 | Astrazeneca Ab | Derivados de morfolino pirimidina utiles en el tratamiento de trastornos proliferativos. |
| WO2008153701A1 (en) * | 2007-05-24 | 2008-12-18 | Schering Corporation | Compounds for inhibiting ksp kinesin activity |
| ATE554075T1 (de) | 2007-07-09 | 2012-05-15 | Astrazeneca Ab | Bei mit mtor-kinase und/oder pi3k in zusammenhang stehenden krankheiten angewendete morpholinopyrimidinderivate |
| PL2300013T5 (pl) | 2008-05-21 | 2025-04-28 | Takeda Pharmaceutical Company Limited | Pochodne fosforu jako inhibitor kinazy |
| US9273077B2 (en) | 2008-05-21 | 2016-03-01 | Ariad Pharmaceuticals, Inc. | Phosphorus derivatives as kinase inhibitors |
| CA2729012A1 (en) | 2008-06-27 | 2009-12-30 | Amgen Inc. | Ang-2 inhibition to treat multiple sclerosis |
| PA8851101A1 (es) * | 2008-12-16 | 2010-07-27 | Lilly Co Eli | Compuesto amino pirazol |
| WO2010096314A1 (en) * | 2009-02-18 | 2010-08-26 | Amgen Inc. | INDOLE/BENZIMIDAZOLE COMPOUNDS AS mTOR KINASE INHIBITORS |
| WO2010100127A1 (en) * | 2009-03-04 | 2010-09-10 | Novartis Ag | Disubstituted imidazole derivatives as modulators of raf kinase |
| SA111320519B1 (ar) * | 2010-06-11 | 2014-07-02 | Astrazeneca Ab | مركبات بيريميدينيل للاستخدام كمثبطات atr |
| WO2011157787A1 (en) * | 2010-06-17 | 2011-12-22 | Novartis Ag | Biphenyl substituted 1,3-dihydro-benzoimidazol-2-ylideneamine derivatives |
| PH12013500547A1 (en) | 2010-09-22 | 2013-06-10 | Arena Pharm Inc | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
| EP2704572B1 (en) | 2011-05-04 | 2015-12-30 | Ariad Pharmaceuticals, Inc. | Compounds for inhibiting cell proliferation in egfr-driven cancers |
| US9061028B2 (en) | 2012-02-15 | 2015-06-23 | Natco Pharma Limited | Process for the preparation of Nilotinib |
| JP6469567B2 (ja) | 2012-05-05 | 2019-02-13 | アリアド・ファーマシューティカルズ・インコーポレイテッド | Ｅｇｆｒ発動性がんの細胞増殖阻害用化合物 |
| KR101469127B1 (ko) * | 2013-03-11 | 2014-12-04 | 한양대학교 에리카산학협력단 | 신규 벤즈이미다졸 유도체, 이의 이성질체 또는 이의 약학적으로 허용 가능한 염, 및 이를 포함하는 약학 조성물 |
| US9611283B1 (en) | 2013-04-10 | 2017-04-04 | Ariad Pharmaceuticals, Inc. | Methods for inhibiting cell proliferation in ALK-driven cancers |
| WO2016014542A1 (en) * | 2014-07-21 | 2016-01-28 | Dana-Farber Cancer Institute, Inc. | Imidazolyl kinase inhibitors and uses thereof |
| KR101850282B1 (ko) * | 2014-11-26 | 2018-05-31 | 한국과학기술연구원 | 단백질 키나아제 저해제로 유용한 헤테로아릴아민 유도체 |
| ES2995737T3 (en) | 2015-01-06 | 2025-02-11 | Arena Pharm Inc | Compound for use in treating conditions related to the s1p1 receptor |
| MA42807A (fr) | 2015-06-22 | 2018-07-25 | Arena Pharm Inc | Sel l-arginine cristallin d'acide (r)-2-(7-(4-cyclopentyl-3-(trifluorométhyl)benzyloxy)-1,2,3,4-tétrahydrocyclo-penta[b]indol-3-yl)acétique (composé 1) pour une utilisation dans des troubles associés au récepteur de s1p1 |
| US9890163B2 (en) | 2015-10-15 | 2018-02-13 | Princeton Drug Discovery Inc | Inhibitors of protein kinases |
| WO2018151873A1 (en) | 2017-02-16 | 2018-08-23 | Arena Pharmaceuticals, Inc. | Compounds and methods for treatment of primary biliary cholangitis |
| KR101840674B1 (ko) | 2017-02-20 | 2018-03-21 | 한양대학교 에리카산학협력단 | Jnk 저해 활성을 갖는 신규한 벤즈이미다졸 유도체 및 이의 용도 |
| EP3801459B1 (en) | 2018-06-06 | 2024-08-07 | Arena Pharmaceuticals, Inc. | Methods of treating conditions related to the s1p1 receptor |
| KR20230084416A (ko) * | 2021-12-03 | 2023-06-13 | 연세대학교 산학협력단 | Wnk3 억제제를 유효성분으로 포함하는 면역관문 억제용 조성물 |
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| SK286264B6 (sk) | 1998-11-17 | 2008-06-06 | Kumiai Chemical Industry Co., Ltd. | Derivát pyrimidinylbenzimidazolu alebo triazinylbenzimidazolu, medziprodukty na jeho prípravu a poľnohospodársky/záhradnícky fungicíd s jeho obsahom |
| US20030004174A9 (en) | 2000-02-17 | 2003-01-02 | Armistead David M. | Kinase inhibitors |
| EP1389617B1 (en) * | 2001-04-27 | 2007-01-03 | Zenyaku Kogyo Kabushiki Kaisha | Heterocyclic compound and antitumor agent containing the same as active ingredient |
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- 2006-06-30 PT PT06774386T patent/PT1899329E/pt unknown
- 2006-06-30 KR KR1020077030728A patent/KR20080015475A/ko not_active Abandoned
- 2006-06-30 EP EP06774386A patent/EP1899329B1/en not_active Not-in-force
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- 2006-06-30 RU RU2008103143/04A patent/RU2386630C2/ru not_active IP Right Cessation
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