CA2477505A1 - Diamino-pyrimidines and their use as angiogenesis inhibitors - Google Patents

Info

Publication number

CA2477505A1

CA2477505A1 CA002477505A CA2477505A CA2477505A1 CA 2477505 A1 CA2477505 A1 CA 2477505A1 CA 002477505 A CA002477505 A CA 002477505A CA 2477505 A CA2477505 A CA 2477505A CA 2477505 A1 CA2477505 A1 CA 2477505A1

Authority

CA

Canada

Prior art keywords

methyl

pyrimidin

amino

benzoimidazol

phenylamino

Prior art date

2002-03-01

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 239000004037 angiogenesis inhibitor Substances 0.000 title description 2
• 229940121369 angiogenesis inhibitor Drugs 0.000 title description 2
• 229940058936 antimalarials diaminopyrimidines Drugs 0.000 title description 2
• MISVBCMQSJUHMH-UHFFFAOYSA-N pyrimidine-4,6-diamine Chemical class NC1=CC(N)=NC=N1 MISVBCMQSJUHMH-UHFFFAOYSA-N 0.000 title 1
• 238000000034 method Methods 0.000 claims abstract description 291
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 46
• 101000753291 Homo sapiens Angiopoietin-1 receptor Proteins 0.000 claims abstract description 36
• 102100022014 Angiopoietin-1 receptor Human genes 0.000 claims abstract description 35
• 238000011282 treatment Methods 0.000 claims abstract description 27
• 229940091171 VEGFR-2 tyrosine kinase inhibitor Drugs 0.000 claims abstract description 5
• 150000001875 compounds Chemical class 0.000 claims description 428
• -1 -NR8R9 Chemical group 0.000 claims description 234
• 229910052739 hydrogen Inorganic materials 0.000 claims description 92
• 239000001257 hydrogen Substances 0.000 claims description 91
• 150000003839 salts Chemical class 0.000 claims description 75
• 125000000217 alkyl group Chemical group 0.000 claims description 73
• 239000012453 solvate Substances 0.000 claims description 63
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 62
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 54
• 125000003118 aryl group Chemical group 0.000 claims description 44
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 42
• 230000000694 effects Effects 0.000 claims description 37
• 102100033177 Vascular endothelial growth factor receptor 2 Human genes 0.000 claims description 34
• 206010028980 Neoplasm Diseases 0.000 claims description 29
• 108010053099 Vascular Endothelial Growth Factor Receptor-2 Proteins 0.000 claims description 28
• 125000003545 alkoxy group Chemical group 0.000 claims description 27
• 239000008194 pharmaceutical composition Substances 0.000 claims description 27
• 230000033115 angiogenesis Effects 0.000 claims description 26
• 241000124008 Mammalia Species 0.000 claims description 25
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 25
• 201000011510 cancer Diseases 0.000 claims description 25
• BJHCYTJNPVGSBZ-YXSASFKJSA-N 1-[4-[6-amino-5-[(Z)-methoxyiminomethyl]pyrimidin-4-yl]oxy-2-chlorophenyl]-3-ethylurea Chemical compound CCNC(=O)Nc1ccc(Oc2ncnc(N)c2\C=N/OC)cc1Cl BJHCYTJNPVGSBZ-YXSASFKJSA-N 0.000 claims description 24
• 125000005843 halogen group Chemical group 0.000 claims description 24
• 125000001072 heteroaryl group Chemical group 0.000 claims description 22
• 125000000623 heterocyclic group Chemical group 0.000 claims description 19
• 239000003795 chemical substances by application Substances 0.000 claims description 18
• 238000002360 preparation method Methods 0.000 claims description 17
• 239000003814 drug Substances 0.000 claims description 16
• 125000001188 haloalkyl group Chemical group 0.000 claims description 16
• 102000009465 Growth Factor Receptors Human genes 0.000 claims description 15
• 108010009202 Growth Factor Receptors Proteins 0.000 claims description 15
• 125000002252 acyl group Chemical group 0.000 claims description 13
• 125000004104 aryloxy group Chemical group 0.000 claims description 12
• 108091008605 VEGF receptors Proteins 0.000 claims description 10
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 10
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
• 230000001404 mediated effect Effects 0.000 claims description 10
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
• 239000002246 antineoplastic agent Substances 0.000 claims description 9
• 125000003435 aroyl group Chemical group 0.000 claims description 8
• 125000004966 cyanoalkyl group Chemical group 0.000 claims description 8
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
• 238000011319 anticancer therapy Methods 0.000 claims description 7
• 229940034982 antineoplastic agent Drugs 0.000 claims description 7
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
• 102000001301 EGF receptor Human genes 0.000 claims description 6
• 108060006698 EGF receptor Proteins 0.000 claims description 6
• 101000851007 Homo sapiens Vascular endothelial growth factor receptor 2 Proteins 0.000 claims description 6
• 239000003085 diluting agent Substances 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 6
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
• 238000002560 therapeutic procedure Methods 0.000 claims description 6
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
• 125000001769 aryl amino group Chemical group 0.000 claims description 5
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
• 229910052760 oxygen Inorganic materials 0.000 claims description 5
• XZWYLPKSDKATEV-UHFFFAOYSA-N 2-(3-methoxyphenyl)-n-[1-methyl-5-[methyl-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]benzimidazol-2-yl]acetamide Chemical compound COC1=CC=CC(CC(=O)NC=2N(C3=CC=C(C=C3N=2)N(C)C=2N=C(NC=3C=CC(CS(C)(=O)=O)=CC=3)N=CC=2)C)=C1 XZWYLPKSDKATEV-UHFFFAOYSA-N 0.000 claims description 4
• SVEPWTZXIDDIJQ-UHFFFAOYSA-N 3-[[4-[[2-[(3-chlorophenyl)methylamino]-1-methylbenzimidazol-5-yl]-methylamino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C=1C=NC(NC=2C=C(C=CC=2)S(N)(=O)=O)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NCC1=CC=CC(Cl)=C1 SVEPWTZXIDDIJQ-UHFFFAOYSA-N 0.000 claims description 4
• 108091008606 PDGF receptors Proteins 0.000 claims description 4
• 102000011653 Platelet-Derived Growth Factor Receptors Human genes 0.000 claims description 4
• 102000009484 Vascular Endothelial Growth Factor Receptors Human genes 0.000 claims description 4
• 102100033178 Vascular endothelial growth factor receptor 1 Human genes 0.000 claims description 4
• 102100033179 Vascular endothelial growth factor receptor 3 Human genes 0.000 claims description 4
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
• 239000001301 oxygen Substances 0.000 claims description 4
• TYDWDJHIOGMALG-UHFFFAOYSA-N 1-(2,5-difluorophenyl)-n-[4-methyl-1-[methyl-[2-(4-methyl-3-sulfamoylanilino)pyrimidin-4-yl]amino]benzimidazol-2-yl]cyclopropane-1-carboxamide Chemical compound C1CC1(C=1C(=CC=C(F)C=1)F)C(=O)NC1=NC2=C(C)C=CC=C2N1N(C)C(N=1)=CC=NC=1NC1=CC=C(C)C(S(N)(=O)=O)=C1 TYDWDJHIOGMALG-UHFFFAOYSA-N 0.000 claims description 3
• LYISPJAHVAQSTK-UHFFFAOYSA-N 1-[1-methyl-5-[methyl-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]benzimidazol-2-yl]-3-phenylurea Chemical compound C=1C=NC(NC=2C=CC(CS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NC(=O)NC1=CC=CC=C1 LYISPJAHVAQSTK-UHFFFAOYSA-N 0.000 claims description 3
• KYFRVPBBRPZBSZ-UHFFFAOYSA-N 2-(2,5-difluorophenyl)-n-[4-methyl-1-[methyl-[2-(4-methyl-3-sulfamoylanilino)pyrimidin-4-yl]amino]benzimidazol-2-yl]acetamide Chemical compound C=1C(F)=CC=C(F)C=1CC(=O)NC1=NC2=C(C)C=CC=C2N1N(C)C(N=1)=CC=NC=1NC1=CC=C(C)C(S(N)(=O)=O)=C1 KYFRVPBBRPZBSZ-UHFFFAOYSA-N 0.000 claims description 3
• PXZKSVXXOAPOFX-UHFFFAOYSA-N 4-methoxy-n-[4-methyl-1-[methyl-[2-(3-morpholin-4-ylsulfonylanilino)pyrimidin-4-yl]amino]benzimidazol-2-yl]benzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NC1=NC2=C(C)C=CC=C2N1N(C)C1=CC=NC(NC=2C=C(C=CC=2)S(=O)(=O)N2CCOCC2)=N1 PXZKSVXXOAPOFX-UHFFFAOYSA-N 0.000 claims description 3
• OWTZECZTNWLOEI-UHFFFAOYSA-N 4-methoxy-n-[4-methyl-1-[methyl-[2-(4-methyl-3-sulfamoylanilino)pyrimidin-4-yl]amino]benzimidazol-2-yl]benzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NC1=NC2=C(C)C=CC=C2N1N(C)C1=CC=NC(NC=2C=C(C(C)=CC=2)S(N)(=O)=O)=N1 OWTZECZTNWLOEI-UHFFFAOYSA-N 0.000 claims description 3
• RRUUVHUXEZBQLY-UHFFFAOYSA-N 4-methyl-1-nitro-n-[3-(trifluoromethyl)phenyl]benzimidazol-2-amine Chemical compound N=1C=2C(C)=CC=CC=2N([N+]([O-])=O)C=1NC1=CC=CC(C(F)(F)F)=C1 RRUUVHUXEZBQLY-UHFFFAOYSA-N 0.000 claims description 3
• KQASEDQMLLAAMH-UHFFFAOYSA-N C1=CC=C2N(C)C(NC(=O)CC)=NC2=C1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 Chemical compound C1=CC=C2N(C)C(NC(=O)CC)=NC2=C1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 KQASEDQMLLAAMH-UHFFFAOYSA-N 0.000 claims description 3
• BOTYLTMPWWCREI-UHFFFAOYSA-N C1=CC=C2N(C)C(NC(=O)CCC)=NC2=C1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 Chemical compound C1=CC=C2N(C)C(NC(=O)CCC)=NC2=C1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 BOTYLTMPWWCREI-UHFFFAOYSA-N 0.000 claims description 3
• LIWYWPUZMVAHLO-UHFFFAOYSA-N C=1C=CC=2N(C)C(NC(=O)C3=COC=C3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 Chemical compound C=1C=CC=2N(C)C(NC(=O)C3=COC=C3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 LIWYWPUZMVAHLO-UHFFFAOYSA-N 0.000 claims description 3
• PMGKBKPAIRJVFV-UHFFFAOYSA-N C=1C=CC=2N(C)C(NC(=O)C3=CSC=C3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 Chemical compound C=1C=CC=2N(C)C(NC(=O)C3=CSC=C3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 PMGKBKPAIRJVFV-UHFFFAOYSA-N 0.000 claims description 3
• AUZWQSGVLAXSCR-UHFFFAOYSA-N C=1C=CC=2N(C)C(NC(=O)C3CC3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 Chemical compound C=1C=CC=2N(C)C(NC(=O)C3CC3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 AUZWQSGVLAXSCR-UHFFFAOYSA-N 0.000 claims description 3
• JYOMTSQYKVXLHD-UHFFFAOYSA-N C=1C=CC=2N(C)C(NC(=O)C=3OC=CC=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 Chemical compound C=1C=CC=2N(C)C(NC(=O)C=3OC=CC=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 JYOMTSQYKVXLHD-UHFFFAOYSA-N 0.000 claims description 3
• ZQFHRHQSZXBWSP-UHFFFAOYSA-N C=1C=CC=2N(C)C(NC(=O)C=3SC=CC=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 Chemical compound C=1C=CC=2N(C)C(NC(=O)C=3SC=CC=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 ZQFHRHQSZXBWSP-UHFFFAOYSA-N 0.000 claims description 3
• OOCAVVWYHYOVRM-UHFFFAOYSA-N C=1C=CC=2N(C)C(NC(=O)CC=3C(=C(F)C=CC=3)F)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 Chemical compound C=1C=CC=2N(C)C(NC(=O)CC=3C(=C(F)C=CC=3)F)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 OOCAVVWYHYOVRM-UHFFFAOYSA-N 0.000 claims description 3
• GSZZYNNCGSLSDW-UHFFFAOYSA-N C=1C=CC=2N(C)C(NC(=O)CC=3C(=CC=CC=3)Cl)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 Chemical compound C=1C=CC=2N(C)C(NC(=O)CC=3C(=CC=CC=3)Cl)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 GSZZYNNCGSLSDW-UHFFFAOYSA-N 0.000 claims description 3
• IGOBGZXAPLDYSP-UHFFFAOYSA-N C=1C=CC=2N(C)C(NC(=O)CC=3C=C(Cl)C=CC=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 Chemical compound C=1C=CC=2N(C)C(NC(=O)CC=3C=C(Cl)C=CC=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 IGOBGZXAPLDYSP-UHFFFAOYSA-N 0.000 claims description 3
• XUISJVYOUZLVAC-UHFFFAOYSA-N C=1C=CC=2N(C)C(NC(=O)CC=3C=CC(Cl)=CC=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 Chemical compound C=1C=CC=2N(C)C(NC(=O)CC=3C=CC(Cl)=CC=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 XUISJVYOUZLVAC-UHFFFAOYSA-N 0.000 claims description 3
• FEQLOGDQKQGSOD-UHFFFAOYSA-N C=1C=CC=2N(C)C(NC(=O)CC=3ON=C(C)C=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 Chemical compound C=1C=CC=2N(C)C(NC(=O)CC=3ON=C(C)C=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 FEQLOGDQKQGSOD-UHFFFAOYSA-N 0.000 claims description 3
• KIPQFNBAOKBBNP-UHFFFAOYSA-N C=1C=CC=2N(C)C(NC(=O)CC=3ON=C(C)C=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 Chemical compound C=1C=CC=2N(C)C(NC(=O)CC=3ON=C(C)C=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 KIPQFNBAOKBBNP-UHFFFAOYSA-N 0.000 claims description 3
• VJNWXBYIVXQIOR-UHFFFAOYSA-N CCS(=O)(=O)C1=CC=C(OC)C(NC=2N=C(C=CN=2)N(C)C=2C=3N=C(NC(=O)C4(CC4)C=4C(=CC=C(F)C=4)F)N(C)C=3C=CC=2)=C1 Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2N=C(C=CN=2)N(C)C=2C=3N=C(NC(=O)C4(CC4)C=4C(=CC=C(F)C=4)F)N(C)C=3C=CC=2)=C1 VJNWXBYIVXQIOR-UHFFFAOYSA-N 0.000 claims description 3
• 101000851018 Homo sapiens Vascular endothelial growth factor receptor 1 Proteins 0.000 claims description 3
• 101000851030 Homo sapiens Vascular endothelial growth factor receptor 3 Proteins 0.000 claims description 3
• AMEUJNYVEPYGHA-UHFFFAOYSA-N [4-[[4-[methyl-[1-methyl-2-(methylamino)benzimidazol-5-yl]amino]pyrimidin-2-yl]amino]phenyl]methanesulfonamide Chemical compound C=1C=C2N(C)C(NC)=NC2=CC=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(N)(=O)=O)C=C1 AMEUJNYVEPYGHA-UHFFFAOYSA-N 0.000 claims description 3
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 3
• BVMVACISWKDUEU-UHFFFAOYSA-N n-[1-methyl-5-[methyl-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]benzimidazol-2-yl]-2-phenylacetamide Chemical compound C=1C=NC(NC=2C=CC(CS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NC(=O)CC1=CC=CC=C1 BVMVACISWKDUEU-UHFFFAOYSA-N 0.000 claims description 3
• MVUVZUGIZRQCAX-UHFFFAOYSA-N n-[4-methyl-1-[methyl-[2-(3-morpholin-4-ylsulfonylanilino)pyrimidin-4-yl]amino]benzimidazol-2-yl]furan-2-carboxamide Chemical compound C=1C=COC=1C(=O)NC1=NC2=C(C)C=CC=C2N1N(C)C(N=1)=CC=NC=1NC(C=1)=CC=CC=1S(=O)(=O)N1CCOCC1 MVUVZUGIZRQCAX-UHFFFAOYSA-N 0.000 claims description 3
• FETPDBRRLFUCAQ-UHFFFAOYSA-N n-[4-methyl-1-[methyl-[2-(3-morpholin-4-ylsulfonylanilino)pyrimidin-4-yl]amino]benzimidazol-2-yl]thiophene-2-carboxamide Chemical compound C=1C=CSC=1C(=O)NC1=NC2=C(C)C=CC=C2N1N(C)C(N=1)=CC=NC=1NC(C=1)=CC=CC=1S(=O)(=O)N1CCOCC1 FETPDBRRLFUCAQ-UHFFFAOYSA-N 0.000 claims description 3
• RCHMSWZTAPEENQ-UHFFFAOYSA-N tert-butyl n-(4-methoxyphenyl)-n-[1-methyl-5-[methyl-[2-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]benzimidazol-2-yl]carbamate Chemical compound C1=CC(OC)=CC=C1N(C(=O)OC(C)(C)C)C1=NC2=CC(N(C)C=3N=C(NC=4C=C(CS(C)(=O)=O)C=CC=4)N=CC=3)=CC=C2N1C RCHMSWZTAPEENQ-UHFFFAOYSA-N 0.000 claims description 3
• IQIKQNNUWRSHOX-UHFFFAOYSA-N tert-butyl n-(4-methyl-1-nitrobenzimidazol-2-yl)-n-[3-(trifluoromethyl)phenyl]carbamate Chemical compound N=1C=2C(C)=CC=CC=2N([N+]([O-])=O)C=1N(C(=O)OC(C)(C)C)C1=CC=CC(C(F)(F)F)=C1 IQIKQNNUWRSHOX-UHFFFAOYSA-N 0.000 claims description 3
• PGGQBCCZVDGRAS-UHFFFAOYSA-N 2-(2,3-dimethoxyphenyl)-n-[1-methyl-5-[methyl-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]benzimidazol-2-yl]acetamide Chemical compound COC1=CC=CC(CC(=O)NC=2N(C3=CC=C(C=C3N=2)N(C)C=2N=C(NC=3C=CC(CS(C)(=O)=O)=CC=3)N=CC=2)C)=C1OC PGGQBCCZVDGRAS-UHFFFAOYSA-N 0.000 claims description 2
• MZWNAJJDJXOZLV-UHFFFAOYSA-N 2-(2,5-difluorophenyl)-n-[4-[[2-(5-ethylsulfonyl-2-methoxyanilino)pyrimidin-4-yl]-methylamino]-1-methylbenzimidazol-2-yl]acetamide Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2N=C(C=CN=2)N(C)C=2C=3N=C(NC(=O)CC=4C(=CC=C(F)C=4)F)N(C)C=3C=CC=2)=C1 MZWNAJJDJXOZLV-UHFFFAOYSA-N 0.000 claims description 2
• QATMPMUKHIHJLS-UHFFFAOYSA-N 2-(2,5-dimethoxyphenyl)-n-[1-methyl-5-[methyl-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]benzimidazol-2-yl]acetamide Chemical compound COC1=CC=C(OC)C(CC(=O)NC=2N(C3=CC=C(C=C3N=2)N(C)C=2N=C(NC=3C=CC(CS(C)(=O)=O)=CC=3)N=CC=2)C)=C1 QATMPMUKHIHJLS-UHFFFAOYSA-N 0.000 claims description 2
• NHMJPJQHCQVSLN-UHFFFAOYSA-N 2-(2-methoxyphenyl)-n-[1-methyl-5-[methyl-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]benzimidazol-2-yl]acetamide Chemical compound COC1=CC=CC=C1CC(=O)NC1=NC2=CC(N(C)C=3N=C(NC=4C=CC(CS(C)(=O)=O)=CC=4)N=CC=3)=CC=C2N1C NHMJPJQHCQVSLN-UHFFFAOYSA-N 0.000 claims description 2
• QDCKWOPBRJZWNI-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-n-[4-methyl-1-[methyl-[2-(4-methyl-3-sulfamoylanilino)pyrimidin-4-yl]amino]benzimidazol-2-yl]acetamide Chemical compound C=1C=C(Cl)C(Cl)=CC=1CC(=O)NC1=NC2=C(C)C=CC=C2N1N(C)C(N=1)=CC=NC=1NC1=CC=C(C)C(S(N)(=O)=O)=C1 QDCKWOPBRJZWNI-UHFFFAOYSA-N 0.000 claims description 2
• GZLRFAKVIBWDAK-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-n-[1-methyl-5-[methyl-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]benzimidazol-2-yl]acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC(=O)NC1=NC2=CC(N(C)C=3N=C(NC=4C=CC(CS(C)(=O)=O)=CC=4)N=CC=3)=CC=C2N1C GZLRFAKVIBWDAK-UHFFFAOYSA-N 0.000 claims description 2
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• QWNWYKIAYZXPEL-UHFFFAOYSA-N C=1C=CC=2N(C)C(NC(=O)CC=3C=C4OCOC4=CC=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 Chemical compound C=1C=CC=2N(C)C(NC(=O)CC=3C=C4OCOC4=CC=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 QWNWYKIAYZXPEL-UHFFFAOYSA-N 0.000 claims description 2
• YHCLYBNNQKLUAW-UHFFFAOYSA-N C=1C=CC=2N(C)C(NC(=O)CC=3C=CC(F)=CC=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 Chemical compound C=1C=CC=2N(C)C(NC(=O)CC=3C=CC(F)=CC=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 YHCLYBNNQKLUAW-UHFFFAOYSA-N 0.000 claims description 2
• DWQZBGVJOATFCG-UHFFFAOYSA-N N-methyl-2-[4-[[4-[methyl-[1-(1-phenylpropan-2-ylamino)benzimidazol-5-yl]amino]pyrimidin-2-yl]amino]phenyl]ethanesulfonamide Chemical compound CNS(=O)(=O)CCC1=CC=C(C=C1)NC1=NC=CC(=N1)N(C1=CC2=C(N(C=N2)NC(CC2=CC=CC=C2)C)C=C1)C DWQZBGVJOATFCG-UHFFFAOYSA-N 0.000 claims description 2
• IBYAJZJDSNWXMS-UHFFFAOYSA-N [3-[[4-[[2-(4-fluoroanilino)-1-methylbenzimidazol-5-yl]-methylamino]pyrimidin-2-yl]amino]phenyl] methanesulfonate Chemical compound C=1C=NC(NC=2C=C(OS(C)(=O)=O)C=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NC1=CC=C(F)C=C1 IBYAJZJDSNWXMS-UHFFFAOYSA-N 0.000 claims description 2
• YATVAEFMOPQUTG-UHFFFAOYSA-N [3-[[4-[[2-[(4-chlorophenyl)methylamino]-1-methylbenzimidazol-5-yl]-methylamino]pyrimidin-2-yl]amino]phenyl] methanesulfonate Chemical compound C=1C=NC(NC=2C=C(OS(C)(=O)=O)C=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NCC1=CC=C(Cl)C=C1 YATVAEFMOPQUTG-UHFFFAOYSA-N 0.000 claims description 2
• QOKGLZLMAPYOHE-UHFFFAOYSA-N [3-[[4-[methyl-[1-methyl-2-(propan-2-ylamino)benzimidazol-5-yl]amino]pyrimidin-2-yl]amino]phenyl] methanesulfonate Chemical compound C=1C=C2N(C)C(NC(C)C)=NC2=CC=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(OS(C)(=O)=O)=C1 QOKGLZLMAPYOHE-UHFFFAOYSA-N 0.000 claims description 2
• QRPLYICUVXYRFX-UHFFFAOYSA-N [4-[[4-[(2-anilino-1-methylbenzimidazol-5-yl)-methylamino]pyrimidin-2-yl]amino]phenyl] methanesulfonate Chemical compound C=1C=NC(NC=2C=CC(OS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NC1=CC=CC=C1 QRPLYICUVXYRFX-UHFFFAOYSA-N 0.000 claims description 2
• SIJHPUOOPUXJFA-UHFFFAOYSA-N [4-[[4-[(2-anilino-1-methylbenzimidazol-5-yl)-methylamino]pyrimidin-2-yl]amino]phenyl]methanesulfonamide Chemical compound C=1C=NC(NC=2C=CC(CS(N)(=O)=O)=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NC1=CC=CC=C1 SIJHPUOOPUXJFA-UHFFFAOYSA-N 0.000 claims description 2
• GZUMRJWAIIJQJO-UHFFFAOYSA-N [4-[[4-[[1-ethyl-2-(methylamino)benzimidazol-5-yl]-methylamino]pyrimidin-2-yl]amino]phenyl]methanesulfonamide Chemical compound C=1C=C2N(CC)C(NC)=NC2=CC=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(N)(=O)=O)C=C1 GZUMRJWAIIJQJO-UHFFFAOYSA-N 0.000 claims description 2
• DEALAAPCCVAXRV-UHFFFAOYSA-N [4-[[4-[[2-(4-fluoroanilino)-1-methylbenzimidazol-5-yl]-methylamino]pyrimidin-2-yl]amino]phenyl] methanesulfonate Chemical compound C=1C=NC(NC=2C=CC(OS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NC1=CC=C(F)C=C1 DEALAAPCCVAXRV-UHFFFAOYSA-N 0.000 claims description 2
• VRZSQFHETDZMBT-UHFFFAOYSA-N [4-[[4-[[2-(4-fluoroanilino)-1-methylbenzimidazol-5-yl]-methylamino]pyrimidin-2-yl]amino]phenyl]methanesulfonamide Chemical compound C=1C=NC(NC=2C=CC(CS(N)(=O)=O)=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NC1=CC=C(F)C=C1 VRZSQFHETDZMBT-UHFFFAOYSA-N 0.000 claims description 2
• FNKOHBYRGMVNLV-UHFFFAOYSA-N [4-[[4-[[2-(4-methoxyanilino)-1-methylbenzimidazol-5-yl]-methylamino]pyrimidin-2-yl]amino]phenyl]methanesulfonamide Chemical compound C1=CC(OC)=CC=C1NC1=NC2=CC(N(C)C=3N=C(NC=4C=CC(CS(N)(=O)=O)=CC=4)N=CC=3)=CC=C2N1C FNKOHBYRGMVNLV-UHFFFAOYSA-N 0.000 claims description 2
• JLKDRQMWQYXCKG-UHFFFAOYSA-N [4-[[4-[[2-(4-tert-butylanilino)-1-methylbenzimidazol-5-yl]-methylamino]pyrimidin-2-yl]amino]phenyl]methanesulfonamide Chemical compound C=1C=NC(NC=2C=CC(CS(N)(=O)=O)=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NC1=CC=C(C(C)(C)C)C=C1 JLKDRQMWQYXCKG-UHFFFAOYSA-N 0.000 claims description 2
• FEDMPXBUDSJLCB-UHFFFAOYSA-N [4-[[4-[[2-(benzylamino)-1-ethylbenzimidazol-5-yl]-methylamino]pyrimidin-2-yl]amino]phenyl]methanesulfonamide Chemical compound N=1C2=CC(N(C)C=3N=C(NC=4C=CC(CS(N)(=O)=O)=CC=4)N=CC=3)=CC=C2N(CC)C=1NCC1=CC=CC=C1 FEDMPXBUDSJLCB-UHFFFAOYSA-N 0.000 claims description 2
• JNLCNQAJFXOOEZ-UHFFFAOYSA-N [4-[[4-[[2-[(2-fluorophenyl)methylamino]-1-methylbenzimidazol-5-yl]-methylamino]pyrimidin-2-yl]amino]phenyl]methanesulfonamide Chemical compound C=1C=NC(NC=2C=CC(CS(N)(=O)=O)=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NCC1=CC=CC=C1F JNLCNQAJFXOOEZ-UHFFFAOYSA-N 0.000 claims description 2
• FLKNSSMMUUGWGN-UHFFFAOYSA-N [4-[[4-[[2-[(3-fluorophenyl)methylamino]-1-methylbenzimidazol-5-yl]-methylamino]pyrimidin-2-yl]amino]phenyl]methanesulfonamide Chemical compound C=1C=NC(NC=2C=CC(CS(N)(=O)=O)=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NCC1=CC=CC(F)=C1 FLKNSSMMUUGWGN-UHFFFAOYSA-N 0.000 claims description 2
• NERYPSMHZHESEH-UHFFFAOYSA-N [4-[[4-[[2-[(4-chlorophenyl)methylamino]-1-methylbenzimidazol-5-yl]-methylamino]pyrimidin-2-yl]amino]phenyl]methanesulfonamide Chemical compound C=1C=NC(NC=2C=CC(CS(N)(=O)=O)=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NCC1=CC=C(Cl)C=C1 NERYPSMHZHESEH-UHFFFAOYSA-N 0.000 claims description 2
• JQLPATKOJYIBON-UHFFFAOYSA-N [4-[[4-[methyl-[1-(1-phenylpropan-2-ylamino)benzimidazol-5-yl]amino]pyrimidin-2-yl]amino]phenyl]methanesulfonamide Chemical compound CN(C1=NC(=NC=C1)NC1=CC=C(C=C1)CS(=O)(=O)N)C1=CC2=C(N(C=N2)NC(CC2=CC=CC=C2)C)C=C1 JQLPATKOJYIBON-UHFFFAOYSA-N 0.000 claims description 2
• HVALVEKVPVMSBS-UHFFFAOYSA-N [4-[[4-[methyl-[1-methyl-2-(1-phenylethylamino)benzimidazol-5-yl]amino]pyrimidin-2-yl]amino]phenyl]methanesulfonamide Chemical compound C=1C=CC=CC=1C(C)NC(N(C1=CC=2)C)=NC1=CC=2N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(N)(=O)=O)C=C1 HVALVEKVPVMSBS-UHFFFAOYSA-N 0.000 claims description 2
• HMKCXHYVJGWKKM-UHFFFAOYSA-N [4-[[4-[methyl-[1-methyl-2-(propan-2-ylamino)benzimidazol-5-yl]amino]pyrimidin-2-yl]amino]phenyl] methanesulfonate Chemical compound C=1C=C2N(C)C(NC(C)C)=NC2=CC=1N(C)C(N=1)=CC=NC=1NC1=CC=C(OS(C)(=O)=O)C=C1 HMKCXHYVJGWKKM-UHFFFAOYSA-N 0.000 claims description 2
• OVQFEQAEBMNKDM-UHFFFAOYSA-N n-[1-methyl-5-[methyl-[2-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]benzimidazol-2-yl]-2-[3-(trifluoromethylsulfanyl)phenyl]acetamide Chemical compound C=1C=NC(NC=2C=C(CS(C)(=O)=O)C=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NC(=O)CC1=CC=CC(SC(F)(F)F)=C1 OVQFEQAEBMNKDM-UHFFFAOYSA-N 0.000 claims description 2
• DPKJPBGMAMNRBP-UHFFFAOYSA-N n-[1-methyl-5-[methyl-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]benzimidazol-2-yl]-1-phenylcyclopropane-1-carboxamide Chemical compound C=1C=NC(NC=2C=CC(CS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NC(=O)C1(C=2C=CC=CC=2)CC1 DPKJPBGMAMNRBP-UHFFFAOYSA-N 0.000 claims description 2
• FLKXTTFHQGBXMJ-UHFFFAOYSA-N n-[1-methyl-5-[methyl-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]benzimidazol-2-yl]-2,3-dihydroindole-1-carboxamide Chemical compound C=1C=C2N(C)C(NC(=O)N3C4=CC=CC=C4CC3)=NC2=CC=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 FLKXTTFHQGBXMJ-UHFFFAOYSA-N 0.000 claims description 2
• NBGGDSPMHASSKR-UHFFFAOYSA-N n-[1-methyl-5-[methyl-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]benzimidazol-2-yl]-2-[3-(trifluoromethylsulfanyl)phenyl]acetamide Chemical compound C=1C=NC(NC=2C=CC(CS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NC(=O)CC1=CC=CC(SC(F)(F)F)=C1 NBGGDSPMHASSKR-UHFFFAOYSA-N 0.000 claims description 2
• HLVFIZOVWCLCCE-UHFFFAOYSA-N n-[1-methyl-5-[methyl-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]benzimidazol-2-yl]-2-phenylmethoxyacetamide Chemical compound C=1C=NC(NC=2C=CC(CS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NC(=O)COCC1=CC=CC=C1 HLVFIZOVWCLCCE-UHFFFAOYSA-N 0.000 claims description 2
• KCFDLEQPPPVHBJ-UHFFFAOYSA-N n-[1-methyl-5-[methyl-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]benzimidazol-2-yl]benzamide Chemical compound C=1C=NC(NC=2C=CC(CS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NC(=O)C1=CC=CC=C1 KCFDLEQPPPVHBJ-UHFFFAOYSA-N 0.000 claims description 2
• JGGSDHJGWNVSNT-UHFFFAOYSA-N n-[1-methyl-5-[methyl-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]benzimidazol-2-yl]cyclohexanecarboxamide Chemical compound C=1C=NC(NC=2C=CC(CS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NC(=O)C1CCCCC1 JGGSDHJGWNVSNT-UHFFFAOYSA-N 0.000 claims description 2
• KDLLRDZCSRHSMF-UHFFFAOYSA-N n-[1-methyl-5-[methyl-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]benzimidazol-2-yl]pyridine-4-carboxamide Chemical compound C=1C=NC(NC=2C=CC(CS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NC(=O)C1=CC=NC=C1 KDLLRDZCSRHSMF-UHFFFAOYSA-N 0.000 claims description 2
• UJESAISRIUHHOS-UHFFFAOYSA-N n-[4-methyl-1-[methyl-[2-(3-morpholin-4-ylsulfonylanilino)pyrimidin-4-yl]amino]benzimidazol-2-yl]-2-(3-methyl-1,2-oxazol-5-yl)acetamide Chemical compound C=1C(C)=NOC=1CC(=O)NC1=NC2=C(C)C=CC=C2N1N(C)C(N=1)=CC=NC=1NC(C=1)=CC=CC=1S(=O)(=O)N1CCOCC1 UJESAISRIUHHOS-UHFFFAOYSA-N 0.000 claims description 2
• YKHSOJKKGGKLDB-UHFFFAOYSA-N n-[4-methyl-1-[methyl-[2-[3-(4-methylpiperazin-1-yl)sulfonylanilino]pyrimidin-4-yl]amino]benzimidazol-2-yl]-2-(3-methyl-1,2-oxazol-5-yl)acetamide Chemical compound C=1C(C)=NOC=1CC(=O)NC1=NC2=C(C)C=CC=C2N1N(C)C(N=1)=CC=NC=1NC(C=1)=CC=CC=1S(=O)(=O)N1CCN(C)CC1 YKHSOJKKGGKLDB-UHFFFAOYSA-N 0.000 claims description 2
• ATHLXSBAMRTTPR-UHFFFAOYSA-N n-[4-methyl-1-[methyl-[2-[3-(4-methylpiperazin-1-yl)sulfonylanilino]pyrimidin-4-yl]amino]benzimidazol-2-yl]furan-2-carboxamide Chemical compound C=1C=COC=1C(=O)NC1=NC2=C(C)C=CC=C2N1N(C)C(N=1)=CC=NC=1NC(C=1)=CC=CC=1S(=O)(=O)N1CCN(C)CC1 ATHLXSBAMRTTPR-UHFFFAOYSA-N 0.000 claims description 2
• OCDBTWZPNSZQHQ-UHFFFAOYSA-N n-[4-methyl-1-[methyl-[2-[3-(4-methylpiperazin-1-yl)sulfonylanilino]pyrimidin-4-yl]amino]benzimidazol-2-yl]thiophene-2-carboxamide Chemical compound C=1C=CSC=1C(=O)NC1=NC2=C(C)C=CC=C2N1N(C)C(N=1)=CC=NC=1NC(C=1)=CC=CC=1S(=O)(=O)N1CCN(C)CC1 OCDBTWZPNSZQHQ-UHFFFAOYSA-N 0.000 claims description 2
• IBOVGHTTXNOAHY-UHFFFAOYSA-N tert-butyl n-(4-methoxyphenyl)-n-[1-methyl-5-[methyl-[2-[4-(1-methylsulfonylethyl)anilino]pyrimidin-4-yl]amino]benzimidazol-2-yl]carbamate Chemical compound C1=CC(OC)=CC=C1N(C(=O)OC(C)(C)C)C1=NC2=CC(N(C)C=3N=C(NC=4C=CC(=CC=4)C(C)S(C)(=O)=O)N=CC=3)=CC=C2N1C IBOVGHTTXNOAHY-UHFFFAOYSA-N 0.000 claims description 2
• STWRZZDDHGYJHE-UHFFFAOYSA-N tert-butyl n-(4-methoxyphenyl)-n-[1-methyl-5-[methyl-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]benzimidazol-2-yl]carbamate Chemical compound C1=CC(OC)=CC=C1N(C(=O)OC(C)(C)C)C1=NC2=CC(N(C)C=3N=C(NC=4C=CC(CS(C)(=O)=O)=CC=4)N=CC=3)=CC=C2N1C STWRZZDDHGYJHE-UHFFFAOYSA-N 0.000 claims description 2
• LUUDFPRMPHSZSX-UHFFFAOYSA-N tert-butyl n-(4-methoxyphenyl)-n-[1-methyl-5-[methyl-[2-[4-(sulfamoylmethyl)anilino]pyrimidin-4-yl]amino]benzimidazol-2-yl]carbamate Chemical compound C1=CC(OC)=CC=C1N(C(=O)OC(C)(C)C)C1=NC2=CC(N(C)C=3N=C(NC=4C=CC(CS(N)(=O)=O)=CC=4)N=CC=3)=CC=C2N1C LUUDFPRMPHSZSX-UHFFFAOYSA-N 0.000 claims description 2
• CAEQKSLEROFPRS-UHFFFAOYSA-N tert-butyl n-[1-methyl-5-[methyl-[2-(3-sulfamoylanilino)pyrimidin-4-yl]amino]benzimidazol-2-yl]-n-phenylcarbamate Chemical compound C=1C=NC(NC=2C=C(C=CC=2)S(N)(=O)=O)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2N(C(=O)OC(C)(C)C)C1=CC=CC=C1 CAEQKSLEROFPRS-UHFFFAOYSA-N 0.000 claims description 2
• ADXFCJYBMPZYON-UHFFFAOYSA-N tert-butyl n-[1-methyl-5-[methyl-[2-(4-methyl-3-sulfamoylanilino)pyrimidin-4-yl]amino]benzimidazol-2-yl]-n-phenylcarbamate Chemical compound C=1C=NC(NC=2C=C(C(C)=CC=2)S(N)(=O)=O)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2N(C(=O)OC(C)(C)C)C1=CC=CC=C1 ADXFCJYBMPZYON-UHFFFAOYSA-N 0.000 claims description 2
• 150000002431 hydrogen Chemical group 0.000 claims 30
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 13
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 10
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 3
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 2
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
• MWWHOIAWYCXKTN-UHFFFAOYSA-N 5-n,1-dimethyl-5-n-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]-2-n-propan-2-ylbenzimidazole-2,5-diamine Chemical compound C=1C=C2N(C)C(NC(C)C)=NC2=CC=1N(C)C(N=1)=CC=NC=1NC1=CC=C(CS(C)(=O)=O)C=C1 MWWHOIAWYCXKTN-UHFFFAOYSA-N 0.000 claims 2
• 108010090091 TIE-2 Receptor Proteins 0.000 claims 2
• 102000012753 TIE-2 Receptor Human genes 0.000 claims 2
• GRHZLQBPAJAHDM-SPRQWYLLSA-N [(3as,4r,6ar)-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-yl] n-[(2s,4s,5s)-5-[[2-(2,6-dimethylphenoxy)acetyl]amino]-4-hydroxy-1,6-diphenylhexan-2-yl]carbamate Chemical compound CC1=CC=CC(C)=C1OCC(=O)N[C@H]([C@@H](O)C[C@H](CC=1C=CC=CC=1)NC(=O)O[C@@H]1[C@@H]2CCO[C@@H]2OC1)CC1=CC=CC=C1 GRHZLQBPAJAHDM-SPRQWYLLSA-N 0.000 claims 2
• 125000006536 (C1-C2)alkoxy group Chemical group 0.000 claims 1
• ITAPLFRHLLOCEL-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-n-[4-methyl-1-[methyl-[2-(4-methyl-3-sulfamoylanilino)pyrimidin-4-yl]amino]benzimidazol-2-yl]cyclopropane-1-carboxamide Chemical compound C1CC1(C=1C=C(Cl)C(Cl)=CC=1)C(=O)NC1=NC2=C(C)C=CC=C2N1N(C)C(N=1)=CC=NC=1NC1=CC=C(C)C(S(N)(=O)=O)=C1 ITAPLFRHLLOCEL-UHFFFAOYSA-N 0.000 claims 1
• BCAWJFDSNFNNGQ-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-[1-methyl-5-[methyl-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]benzimidazol-2-yl]urea Chemical compound C=1C=NC(NC=2C=CC(CS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NC(=O)NC=1C=C(C(C)(C)C)ON=1 BCAWJFDSNFNNGQ-UHFFFAOYSA-N 0.000 claims 1
• RQMVPNXYNWUDJM-UHFFFAOYSA-N 2-[4-[[4-[[2-(benzylamino)-1-methylbenzimidazol-5-yl]-methylamino]pyrimidin-2-yl]amino]phenyl]-n-methylethanesulfonamide Chemical compound C1=CC(CCS(=O)(=O)NC)=CC=C1NC1=NC=CC(N(C)C=2C=C3N=C(NCC=4C=CC=CC=4)N(C)C3=CC=2)=N1 RQMVPNXYNWUDJM-UHFFFAOYSA-N 0.000 claims 1
• PJPVFWAHEFAFPJ-UHFFFAOYSA-N 2-[4-[[4-[[2-[(4-fluorophenyl)methylamino]-1-methylbenzimidazol-5-yl]-methylamino]pyrimidin-2-yl]amino]phenyl]-n-methylethanesulfonamide Chemical compound C1=CC(CCS(=O)(=O)NC)=CC=C1NC1=NC=CC(N(C)C=2C=C3N=C(NCC=4C=CC(F)=CC=4)N(C)C3=CC=2)=N1 PJPVFWAHEFAFPJ-UHFFFAOYSA-N 0.000 claims 1
• NMZWIFIUVBUUBO-UHFFFAOYSA-N 2-[4-[[4-[[2-[(4-methoxyphenyl)methylamino]-1-methylbenzimidazol-5-yl]-methylamino]pyrimidin-2-yl]amino]phenyl]-n-methylethanesulfonamide Chemical compound C1=CC(CCS(=O)(=O)NC)=CC=C1NC1=NC=CC(N(C)C=2C=C3N=C(NCC=4C=CC(OC)=CC=4)N(C)C3=CC=2)=N1 NMZWIFIUVBUUBO-UHFFFAOYSA-N 0.000 claims 1
• LLJGESJIVOHITE-UHFFFAOYSA-N 2-chloro-5-[[4-[methyl-[1-methyl-2-(propan-2-ylamino)benzimidazol-5-yl]amino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C=1C=C2N(C)C(NC(C)C)=NC2=CC=1N(C)C(N=1)=CC=NC=1NC1=CC=C(Cl)C(S(N)(=O)=O)=C1 LLJGESJIVOHITE-UHFFFAOYSA-N 0.000 claims 1
• FABKGOCUUDJZEW-UHFFFAOYSA-N 2-methyl-5-[[4-[methyl-[1-methyl-2-[(4-methylphenyl)methylamino]benzimidazol-5-yl]amino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C=1C=NC(NC=2C=C(C(C)=CC=2)S(N)(=O)=O)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NCC1=CC=C(C)C=C1 FABKGOCUUDJZEW-UHFFFAOYSA-N 0.000 claims 1
• DALAMVJDYIXYFQ-UHFFFAOYSA-N 2-n,5-n,1-trimethyl-5-n-[2-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]benzimidazole-2,5-diamine Chemical compound C=1C=C2N(C)C(NC)=NC2=CC=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 DALAMVJDYIXYFQ-UHFFFAOYSA-N 0.000 claims 1
• FLLRIPMRUBLNHW-UHFFFAOYSA-N 2-n-(2,4-dichlorophenyl)-5-n,1-dimethyl-5-n-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]benzimidazole-2,5-diamine Chemical compound C=1C=NC(NC=2C=CC(CS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NC1=CC=C(Cl)C=C1Cl FLLRIPMRUBLNHW-UHFFFAOYSA-N 0.000 claims 1
• AXVJLPIEADTVGD-UHFFFAOYSA-N 2-n-(2,4-difluorophenyl)-5-n,1-dimethyl-5-n-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]benzimidazole-2,5-diamine Chemical compound C=1C=NC(NC=2C=CC(CS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NC1=CC=C(F)C=C1F AXVJLPIEADTVGD-UHFFFAOYSA-N 0.000 claims 1
• KMIAVQMVMBUWMK-UHFFFAOYSA-N 2-n-(2,5-dichlorophenyl)-5-n,1-dimethyl-5-n-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]benzimidazole-2,5-diamine Chemical compound C=1C=NC(NC=2C=CC(CS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NC1=CC(Cl)=CC=C1Cl KMIAVQMVMBUWMK-UHFFFAOYSA-N 0.000 claims 1
• KSEXSUXXTOYYIO-UHFFFAOYSA-N 2-n-(2-chloro-4-fluorophenyl)-5-n,1-dimethyl-5-n-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]benzimidazole-2,5-diamine Chemical compound C=1C=NC(NC=2C=CC(CS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NC1=CC=C(F)C=C1Cl KSEXSUXXTOYYIO-UHFFFAOYSA-N 0.000 claims 1
• SLTNPYPMNCWSQX-UHFFFAOYSA-N 2-n-(2-chloro-5-fluorophenyl)-5-n,1-dimethyl-5-n-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]benzimidazole-2,5-diamine Chemical compound C=1C=NC(NC=2C=CC(CS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NC1=CC(F)=CC=C1Cl SLTNPYPMNCWSQX-UHFFFAOYSA-N 0.000 claims 1
• HALUPUJTNMXRFM-UHFFFAOYSA-N 2-n-(2-fluoro-4-methylphenyl)-5-n,1-dimethyl-5-n-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]benzimidazole-2,5-diamine Chemical compound C=1C=NC(NC=2C=CC(CS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NC1=CC=C(C)C=C1F HALUPUJTNMXRFM-UHFFFAOYSA-N 0.000 claims 1
• MIHWIKPYLDXQRI-UHFFFAOYSA-N 2-n-(2-fluorophenyl)-5-n,1-dimethyl-5-n-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]benzimidazole-2,5-diamine Chemical compound C=1C=NC(NC=2C=CC(CS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NC1=CC=CC=C1F MIHWIKPYLDXQRI-UHFFFAOYSA-N 0.000 claims 1
• SEJKRTUGFQMRQC-UHFFFAOYSA-N 2-n-(3-chlorophenyl)-5-n,1-dimethyl-5-n-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]benzimidazole-2,5-diamine Chemical compound C=1C=NC(NC=2C=CC(CS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NC1=CC=CC(Cl)=C1 SEJKRTUGFQMRQC-UHFFFAOYSA-N 0.000 claims 1
• QCVMDUMYRAFMJM-UHFFFAOYSA-N 2-n-(3-fluorophenyl)-5-n,1-dimethyl-5-n-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]benzimidazole-2,5-diamine Chemical compound C=1C=NC(NC=2C=CC(CS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NC1=CC=CC(F)=C1 QCVMDUMYRAFMJM-UHFFFAOYSA-N 0.000 claims 1
• KAVKAVXVBGTHLL-UHFFFAOYSA-N 2-n-(4-chloro-2-fluorophenyl)-5-n,1-dimethyl-5-n-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]benzimidazole-2,5-diamine Chemical compound C=1C=NC(NC=2C=CC(CS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NC1=CC=C(Cl)C=C1F KAVKAVXVBGTHLL-UHFFFAOYSA-N 0.000 claims 1
• YBQZMWGBFSNDPL-UHFFFAOYSA-N 2-n-(4-chlorophenyl)-5-n,1-dimethyl-5-n-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]benzimidazole-2,5-diamine Chemical compound C=1C=NC(NC=2C=CC(CS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NC1=CC=C(Cl)C=C1 YBQZMWGBFSNDPL-UHFFFAOYSA-N 0.000 claims 1
• LLZLLWYQIKYQSZ-UHFFFAOYSA-N 2-n-(4-fluorophenyl)-5-n,1-dimethyl-5-n-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]benzimidazole-2,5-diamine Chemical compound C=1C=NC(NC=2C=CC(CS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NC1=CC=C(F)C=C1 LLZLLWYQIKYQSZ-UHFFFAOYSA-N 0.000 claims 1
• JFYVOEQDKWYWFA-UHFFFAOYSA-N 2-n-(4-methoxyphenyl)-5-n,1-dimethyl-5-n-[2-[3-(1-methylsulfonylethyl)anilino]pyrimidin-4-yl]benzimidazole-2,5-diamine Chemical compound C1=CC(OC)=CC=C1NC1=NC2=CC(N(C)C=3N=C(NC=4C=C(C=CC=4)C(C)S(C)(=O)=O)N=CC=3)=CC=C2N1C JFYVOEQDKWYWFA-UHFFFAOYSA-N 0.000 claims 1
• XTRUMJNLLCOOLU-UHFFFAOYSA-N 2-n-(4-methoxyphenyl)-5-n,1-dimethyl-5-n-[2-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]benzimidazole-2,5-diamine Chemical compound C1=CC(OC)=CC=C1NC1=NC2=CC(N(C)C=3N=C(NC=4C=C(CS(C)(=O)=O)C=CC=4)N=CC=3)=CC=C2N1C XTRUMJNLLCOOLU-UHFFFAOYSA-N 0.000 claims 1
• WDAJCVYEIINXKV-UHFFFAOYSA-N 2-n-(4-methoxyphenyl)-5-n,1-dimethyl-5-n-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]benzimidazole-2,5-diamine Chemical compound C1=CC(OC)=CC=C1NC1=NC2=CC(N(C)C=3N=C(NC=4C=CC(CS(C)(=O)=O)=CC=4)N=CC=3)=CC=C2N1C WDAJCVYEIINXKV-UHFFFAOYSA-N 0.000 claims 1
• PCJDDLGEZSEBEI-UHFFFAOYSA-N 2-n-(4-tert-butylphenyl)-5-n,1-dimethyl-5-n-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]benzimidazole-2,5-diamine Chemical compound C=1C=NC(NC=2C=CC(CS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NC1=CC=C(C(C)(C)C)C=C1 PCJDDLGEZSEBEI-UHFFFAOYSA-N 0.000 claims 1
• BKJOJFMMSCWEIX-UHFFFAOYSA-N 2-n-(5-tert-butyl-1,2-oxazol-3-yl)-1-methyl-5-n-[2-(3-morpholin-4-ylsulfonylanilino)pyrimidin-4-yl]benzimidazole-2,5-diamine Chemical compound N=1C2=CC(NC=3N=C(NC=4C=C(C=CC=4)S(=O)(=O)N4CCOCC4)N=CC=3)=CC=C2N(C)C=1NC=1C=C(C(C)(C)C)ON=1 BKJOJFMMSCWEIX-UHFFFAOYSA-N 0.000 claims 1
• LMABTRIYPBDTMI-UHFFFAOYSA-N 2-n-(5-tert-butyl-1,2-oxazol-3-yl)-1-methyl-5-n-[2-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]benzimidazole-2,5-diamine Chemical compound N=1C2=CC(NC=3N=C(NC=4C=C(CS(C)(=O)=O)C=CC=4)N=CC=3)=CC=C2N(C)C=1NC=1C=C(C(C)(C)C)ON=1 LMABTRIYPBDTMI-UHFFFAOYSA-N 0.000 claims 1
• BTZDKMWXWYLPDX-UHFFFAOYSA-N 2-n-[(3-fluorophenyl)methyl]-5-n,1-dimethyl-5-n-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]benzimidazole-2,5-diamine Chemical compound C=1C=NC(NC=2C=CC(CS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NCC1=CC=CC(F)=C1 BTZDKMWXWYLPDX-UHFFFAOYSA-N 0.000 claims 1
• YTEGOXPEDYAQCH-UHFFFAOYSA-N 2-n-[(4-chlorophenyl)methyl]-5-n,1-dimethyl-5-n-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]benzimidazole-2,5-diamine Chemical compound C=1C=NC(NC=2C=CC(CS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NCC1=CC=C(Cl)C=C1 YTEGOXPEDYAQCH-UHFFFAOYSA-N 0.000 claims 1
• GPTCYKQEGNCZMK-UHFFFAOYSA-N 2-n-[(4-fluorophenyl)methyl]-5-n,1-dimethyl-5-n-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]benzimidazole-2,5-diamine Chemical compound C=1C=NC(NC=2C=CC(CS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NCC1=CC=C(F)C=C1 GPTCYKQEGNCZMK-UHFFFAOYSA-N 0.000 claims 1
• NVWPXCLZSUOOGE-UHFFFAOYSA-N 2-n-[(4-methoxyphenyl)methyl]-5-n,1-dimethyl-5-n-[2-[3-(2-methylsulfonylethyl)anilino]pyrimidin-4-yl]benzimidazole-2,5-diamine Chemical compound C1=CC(OC)=CC=C1CNC1=NC2=CC(N(C)C=3N=C(NC=4C=C(CCS(C)(=O)=O)C=CC=4)N=CC=3)=CC=C2N1C NVWPXCLZSUOOGE-UHFFFAOYSA-N 0.000 claims 1
• IEHOSHUACRZHOP-UHFFFAOYSA-N 2-n-[(4-methoxyphenyl)methyl]-5-n,1-dimethyl-5-n-[2-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]benzimidazole-2,5-diamine Chemical compound C1=CC(OC)=CC=C1CNC1=NC2=CC(N(C)C=3N=C(NC=4C=C(CS(C)(=O)=O)C=CC=4)N=CC=3)=CC=C2N1C IEHOSHUACRZHOP-UHFFFAOYSA-N 0.000 claims 1
• YIVNZELPYQRBKJ-UHFFFAOYSA-N 2-n-[(4-methoxyphenyl)methyl]-5-n,1-dimethyl-5-n-[2-[4-(1-methylsulfonylethyl)anilino]pyrimidin-4-yl]benzimidazole-2,5-diamine Chemical compound C1=CC(OC)=CC=C1CNC1=NC2=CC(N(C)C=3N=C(NC=4C=CC(=CC=4)C(C)S(C)(=O)=O)N=CC=3)=CC=C2N1C YIVNZELPYQRBKJ-UHFFFAOYSA-N 0.000 claims 1
• CBULCEORGNBFOY-UHFFFAOYSA-N 2-n-[(4-methoxyphenyl)methyl]-5-n,1-dimethyl-5-n-[2-[4-(2-methylsulfonylethyl)anilino]pyrimidin-4-yl]benzimidazole-2,5-diamine Chemical compound C1=CC(OC)=CC=C1CNC1=NC2=CC(N(C)C=3N=C(NC=4C=CC(CCS(C)(=O)=O)=CC=4)N=CC=3)=CC=C2N1C CBULCEORGNBFOY-UHFFFAOYSA-N 0.000 claims 1
• IHDXVZVIYJNIRR-UHFFFAOYSA-N 2-n-[(4-methoxyphenyl)methyl]-5-n,1-dimethyl-5-n-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]benzimidazole-2,5-diamine Chemical compound C1=CC(OC)=CC=C1CNC1=NC2=CC(N(C)C=3N=C(NC=4C=CC(CS(C)(=O)=O)=CC=4)N=CC=3)=CC=C2N1C IHDXVZVIYJNIRR-UHFFFAOYSA-N 0.000 claims 1
• JQDGGMOYRAETSW-UHFFFAOYSA-N 2-n-[2-chloro-4-(trifluoromethyl)phenyl]-5-n,1-dimethyl-5-n-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]benzimidazole-2,5-diamine Chemical compound C=1C=NC(NC=2C=CC(CS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NC1=CC=C(C(F)(F)F)C=C1Cl JQDGGMOYRAETSW-UHFFFAOYSA-N 0.000 claims 1
• YOKXLSDJJXTORM-UHFFFAOYSA-N 2-n-[2-chloro-5-(trifluoromethyl)phenyl]-5-n,1-dimethyl-5-n-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]benzimidazole-2,5-diamine Chemical compound C=1C=NC(NC=2C=CC(CS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NC1=CC(C(F)(F)F)=CC=C1Cl YOKXLSDJJXTORM-UHFFFAOYSA-N 0.000 claims 1
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