JP2005524668A - ジアミノピリミジン類及びそれらの血管新生阻害薬としての使用 - Google Patents

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Publication number

JP2005524668A

JP2005524668A JP2003572983A JP2003572983A JP2005524668A JP 2005524668 A JP2005524668 A JP 2005524668A JP 2003572983 A JP2003572983 A JP 2003572983A JP 2003572983 A JP2003572983 A JP 2003572983A JP 2005524668 A JP2005524668 A JP 2005524668A

Authority

JP

Japan

Prior art keywords

methyl

pyrimidin

amino

phenylamino

benzimidazol

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.)

Pending

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• Global Dossier
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• 229940121369 angiogenesis inhibitor Drugs 0.000 title 1
• 239000004037 angiogenesis inhibitor Substances 0.000 title 1
• 229940058936 antimalarials diaminopyrimidines Drugs 0.000 title 1
• 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 295
• 102100033177 Vascular endothelial growth factor receptor 2 Human genes 0.000 claims abstract description 40
• 101000753291 Homo sapiens Angiopoietin-1 receptor Proteins 0.000 claims abstract description 38
• 102100022014 Angiopoietin-1 receptor Human genes 0.000 claims abstract description 37
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 37
• 108010053099 Vascular Endothelial Growth Factor Receptor-2 Proteins 0.000 claims abstract description 35
• 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 abstract description 32
• 238000011282 treatment Methods 0.000 claims abstract description 16
• 150000001875 compounds Chemical class 0.000 claims description 426
• -1 —NR 8 R 9 Chemical group 0.000 claims description 424
• 229910052739 hydrogen Inorganic materials 0.000 claims description 96
• 239000001257 hydrogen Substances 0.000 claims description 91
• 150000003839 salts Chemical class 0.000 claims description 83
• 150000002431 hydrogen Chemical group 0.000 claims description 67
• 125000000217 alkyl group Chemical group 0.000 claims description 65
• 239000012453 solvate Substances 0.000 claims description 61
• 150000001408 amides Chemical class 0.000 claims description 50
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 46
• 125000003118 aryl group Chemical group 0.000 claims description 44
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 41
• 230000000694 effects Effects 0.000 claims description 38
• 208000035475 disorder Diseases 0.000 claims description 31
• 230000033115 angiogenesis Effects 0.000 claims description 29
• 239000003814 drug Substances 0.000 claims description 29
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 26
• 239000008194 pharmaceutical composition Substances 0.000 claims description 26
• 206010028980 Neoplasm Diseases 0.000 claims description 25
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
• 201000011510 cancer Diseases 0.000 claims description 24
• 230000006870 function Effects 0.000 claims description 24
• 125000005843 halogen group Chemical group 0.000 claims description 24
• 241000124008 Mammalia Species 0.000 claims description 23
• 125000001072 heteroaryl group Chemical group 0.000 claims description 23
• 229940079593 drug Drugs 0.000 claims description 22
• 125000003545 alkoxy group Chemical group 0.000 claims description 21
• 125000000623 heterocyclic group Chemical group 0.000 claims description 19
• 239000002246 antineoplastic agent Substances 0.000 claims description 17
• 102000009465 Growth Factor Receptors Human genes 0.000 claims description 15
• 108010009202 Growth Factor Receptors Proteins 0.000 claims description 15
• 239000002904 solvent Substances 0.000 claims description 14
• SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 claims description 12
• 125000002252 acyl group Chemical group 0.000 claims description 12
• 125000004104 aryloxy group Chemical group 0.000 claims description 12
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 11
• 108091008605 VEGF receptors Proteins 0.000 claims description 10
• 102000009484 Vascular Endothelial Growth Factor Receptors Human genes 0.000 claims description 10
• 229940034982 antineoplastic agent Drugs 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
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
• 125000001188 haloalkyl group Chemical group 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
• 125000004438 haloalkoxy group Chemical group 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
• 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 6
• BNYIQEFWGSXIKQ-UHFFFAOYSA-N 3-methylfuran-2-carboxylic acid Chemical compound CC=1C=COC=1C(O)=O BNYIQEFWGSXIKQ-UHFFFAOYSA-N 0.000 claims description 6
• IFLKEBSJTZGCJG-UHFFFAOYSA-N 3-methylthiophene-2-carboxylic acid Chemical compound CC=1C=CSC=1C(O)=O IFLKEBSJTZGCJG-UHFFFAOYSA-N 0.000 claims description 6
• 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
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 6
• 239000003085 diluting agent Substances 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
• 125000004765 (C1-C4) haloalkyl group Chemical group 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
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
• 229910052760 oxygen Inorganic materials 0.000 claims description 5
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
• 229940124597 therapeutic agent Drugs 0.000 claims description 5
• 238000002560 therapeutic procedure Methods 0.000 claims description 5
• 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 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
• RCKNAENLAPRPBW-UHFFFAOYSA-N C=1C=CC=2N(C)C(NC(=O)C=3C=C4NC=NC4=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=3C=C4NC=NC4=CC=3)=NC=2C=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 RCKNAENLAPRPBW-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
• 229940091171 VEGFR-2 tyrosine kinase inhibitor Drugs 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
• 239000001301 oxygen Substances 0.000 claims description 4
• QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 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
• 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 description 3
• 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 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
• 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 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
• 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 3
• 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 3
• IOYCCLXBNASNOV-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-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=C(Cl)C(Cl)=CC=4)N(C)C=3C=CC=2)=C1 IOYCCLXBNASNOV-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• 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 3
• XBLMGJGVFXRKFD-UHFFFAOYSA-N 2-(3,5-dimethoxyphenyl)-n-[1-methyl-5-[methyl-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]benzimidazol-2-yl]acetamide Chemical compound COC1=CC(OC)=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 XBLMGJGVFXRKFD-UHFFFAOYSA-N 0.000 claims description 3
• TVVHQKVXGSTWOE-UHFFFAOYSA-N 2-(5-tert-butyl-1,2-oxazol-3-yl)-1-methyl-5-N-[2-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]-3H-benzimidazole-2,5-diamine Chemical compound C(C)(C)(C)C1=CC(=NO1)C1(NC2=C(N1C)C=CC(=C2)NC1=NC(=NC=C1)NC1=CC(=CC=C1)CS(=O)(=O)C)N TVVHQKVXGSTWOE-UHFFFAOYSA-N 0.000 claims description 3
• PVLQQOOFOKCMAJ-UHFFFAOYSA-N 3-[[4-[[2-(benzylamino)-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=C1 PVLQQOOFOKCMAJ-UHFFFAOYSA-N 0.000 claims description 3
• CKKNJWOTUSTMLF-UHFFFAOYSA-N 3-[[4-[methyl-[1-methyl-2-(methylamino)benzimidazol-5-yl]amino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C=1C=C2N(C)C(NC)=NC2=CC=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(S(N)(=O)=O)=C1 CKKNJWOTUSTMLF-UHFFFAOYSA-N 0.000 claims description 3
• AQWYJZJPVSMTLU-UHFFFAOYSA-N 4-[[4-[methyl-(1-methyl-2-methylsulfanylbenzimidazol-5-yl)amino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C=1C=C2N(C)C(SC)=NC2=CC=1N(C)C(N=1)=CC=NC=1NC1=CC=C(S(N)(=O)=O)C=C1 AQWYJZJPVSMTLU-UHFFFAOYSA-N 0.000 claims description 3
• BTQNREUEBQJRML-UHFFFAOYSA-N 4-[[4-[methyl-(1-methyl-2-methylsulfinylbenzimidazol-5-yl)amino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C=1C=C2N(C)C(S(C)=O)=NC2=CC=1N(C)C(N=1)=CC=NC=1NC1=CC=C(S(N)(=O)=O)C=C1 BTQNREUEBQJRML-UHFFFAOYSA-N 0.000 claims description 3
• URBGGDNKOFNDAH-UHFFFAOYSA-N 4-[[4-[methyl-[1-methyl-2-[4-(trifluoromethyl)anilino]benzimidazol-5-yl]amino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C=1C=NC(NC=2C=CC(=CC=2)S(N)(=O)=O)=NC=1N(C)C(C=C1N=2)=CC=C1N(C)C=2NC1=CC=C(C(F)(F)F)C=C1 URBGGDNKOFNDAH-UHFFFAOYSA-N 0.000 claims description 3
• SEMACTOEPIEMPC-UHFFFAOYSA-N 5-[[4-[[2-(benzylamino)-1-methylbenzimidazol-5-yl]-methylamino]pyrimidin-2-yl]amino]-n-methoxy-2-methylbenzenesulfonamide Chemical compound C1=C(C)C(S(=O)(=O)NOC)=CC(NC=2N=C(C=CN=2)N(C)C=2C=C3N=C(NCC=4C=CC=CC=4)N(C)C3=CC=2)=C1 SEMACTOEPIEMPC-UHFFFAOYSA-N 0.000 claims description 3
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• MXKIEMGHMAQAFR-UHFFFAOYSA-N N-[4-[[4-[methyl-[1-methyl-2-(methylamino)benzimidazol-5-yl]amino]pyrimidin-2-yl]amino]phenyl]methanesulfonamide Chemical compound CNc1nc2cc(ccc2n1C)N(C)c1ccnc(Nc2ccc(NS(C)(=O)=O)cc2)n1 MXKIEMGHMAQAFR-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
• 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
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• 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
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