BRPI0613501A2 - composto, composição farmacêutica e uso do mesmo - Google Patents

Info

Publication number

BRPI0613501A2

BRPI0613501A2 BRPI0613501-3A BRPI0613501A BRPI0613501A2 BR PI0613501 A2 BRPI0613501 A2 BR PI0613501A2 BR PI0613501 A BRPI0613501 A BR PI0613501A BR PI0613501 A2 BRPI0613501 A2 BR PI0613501A2

Authority

BR

Brazil

Prior art keywords

methyl

pyrimidin

benzoimidazol

phenyl

ylamino

Prior art date

2005-07-01

Links

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 144
• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 17
• 102100027842 Fibroblast growth factor receptor 3 Human genes 0.000 claims abstract description 27
• 101710182396 Fibroblast growth factor receptor 3 Proteins 0.000 claims abstract description 27
• 108060006706 SRC Proteins 0.000 claims abstract description 14
• 102000001332 SRC Human genes 0.000 claims abstract description 14
• 102100033177 Vascular endothelial growth factor receptor 2 Human genes 0.000 claims abstract description 11
• 108010053099 Vascular Endothelial Growth Factor Receptor-2 Proteins 0.000 claims abstract description 10
• -1 cyano, hydroxy Chemical group 0.000 claims description 245
• 125000000217 alkyl group Chemical group 0.000 claims description 51
• 108091000080 Phosphotransferase Proteins 0.000 claims description 47
• 102000020233 phosphotransferase Human genes 0.000 claims description 47
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 43
• 201000010099 disease Diseases 0.000 claims description 31
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 31
• 239000001257 hydrogen Substances 0.000 claims description 29
• 229910052739 hydrogen Inorganic materials 0.000 claims description 29
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 27
• 125000001072 heteroaryl group Chemical group 0.000 claims description 27
• 150000003839 salts Chemical class 0.000 claims description 22
• 125000003118 aryl group Chemical group 0.000 claims description 20
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 16
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
• 150000003254 radicals Chemical class 0.000 claims description 16
• 101150028321 Lck gene Proteins 0.000 claims description 15
• 125000001475 halogen functional group Chemical group 0.000 claims description 15
• 108010029869 Proto-Oncogene Proteins c-raf Proteins 0.000 claims description 14
• 102100031167 Tyrosine-protein kinase CSK Human genes 0.000 claims description 13
• 101100481408 Danio rerio tie2 gene Proteins 0.000 claims description 12
• 101100481410 Mus musculus Tek gene Proteins 0.000 claims description 12
• 239000002253 acid Substances 0.000 claims description 12
• 125000003545 alkoxy group Chemical group 0.000 claims description 12
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
• 101150036586 FES gene Proteins 0.000 claims description 11
• 101150003567 Mapk12 gene Proteins 0.000 claims description 11
• 102000056243 Mitogen-activated protein kinase 12 Human genes 0.000 claims description 11
• 108700015929 Mitogen-activated protein kinase 12 Proteins 0.000 claims description 11
• 101150056950 Ntrk2 gene Proteins 0.000 claims description 11
• 101150071831 RPS6KA1 gene Proteins 0.000 claims description 11
• 101150105578 SAPK3 gene Proteins 0.000 claims description 11
• 102000052116 epidermal growth factor receptor activity proteins Human genes 0.000 claims description 11
• 108700015053 epidermal growth factor receptor activity proteins Proteins 0.000 claims description 11
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
• 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 description 11
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 10
• 101000742982 Homo sapiens Serine/threonine-protein kinase WNK3 Proteins 0.000 claims description 10
• 101000997832 Homo sapiens Tyrosine-protein kinase JAK2 Proteins 0.000 claims description 10
• 101000934996 Homo sapiens Tyrosine-protein kinase JAK3 Proteins 0.000 claims description 10
• 108700012928 MAPK14 Proteins 0.000 claims description 10
• 102000054819 Mitogen-activated protein kinase 14 Human genes 0.000 claims description 10
• 102100038115 Serine/threonine-protein kinase WNK3 Human genes 0.000 claims description 10
• 102100033444 Tyrosine-protein kinase JAK2 Human genes 0.000 claims description 10
• 102100025387 Tyrosine-protein kinase JAK3 Human genes 0.000 claims description 10
• 125000001188 haloalkyl group Chemical group 0.000 claims description 10
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 9
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 9
• 102100027907 Cytoplasmic tyrosine-protein kinase BMX Human genes 0.000 claims description 9
• 101100354317 Mus musculus Ptk6 gene Proteins 0.000 claims description 9
• 101150083487 SIK1 gene Proteins 0.000 claims description 9
• 125000002947 alkylene group Chemical group 0.000 claims description 9
• 150000002431 hydrogen Chemical class 0.000 claims description 9
• 230000001404 mediated effect Effects 0.000 claims description 9
• 101150053778 CSF1R gene Proteins 0.000 claims description 8
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
• 102100039810 Protein-tyrosine kinase 6 Human genes 0.000 claims description 8
• 101150060629 def gene Proteins 0.000 claims description 8
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 7
• 101100503636 Danio rerio fyna gene Proteins 0.000 claims description 7
• 101150018272 FYN gene Proteins 0.000 claims description 7
• 101100091501 Mus musculus Ros1 gene Proteins 0.000 claims description 7
• 101100091511 Rhizobium radiobacter ros gene Proteins 0.000 claims description 7
• 229910052757 nitrogen Inorganic materials 0.000 claims description 7
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
• 125000004076 pyridyl group Chemical group 0.000 claims description 7
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 6
• 101100240519 Caenorhabditis elegans nhr-13 gene Proteins 0.000 claims description 6
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 5
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 5
• 125000004193 piperazinyl group Chemical group 0.000 claims description 5
• 125000001424 substituent group Chemical group 0.000 claims description 5
• 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 4
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
• 125000003386 piperidinyl group Chemical group 0.000 claims description 4
• 238000002360 preparation method Methods 0.000 claims description 4
• 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 3
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
• 125000002541 furyl group Chemical group 0.000 claims description 3
• 125000002883 imidazolyl group Chemical group 0.000 claims description 3
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
• CXGURYCBXAXZNF-UHFFFAOYSA-N n-(3,5-dimethoxyphenyl)-1-[6-(4-morpholin-4-ylanilino)pyrimidin-4-yl]benzimidazol-2-amine Chemical compound COC1=CC(OC)=CC(NC=2N(C3=CC=CC=C3N=2)C=2N=CN=C(NC=3C=CC(=CC=3)N3CCOCC3)C=2)=C1 CXGURYCBXAXZNF-UHFFFAOYSA-N 0.000 claims description 3
• HTEUQPWFMDGLKN-UHFFFAOYSA-N n-[3-[[1-(6-aminopyrimidin-4-yl)benzimidazol-2-yl]amino]-4-methylphenyl]-3-(4-ethylpiperazin-1-yl)-5-(trifluoromethyl)benzamide Chemical compound C1CN(CC)CCN1C1=CC(C(=O)NC=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 HTEUQPWFMDGLKN-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 3
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• OBOOCHGOPNGGLO-UHFFFAOYSA-N 1-pyrrolidin-1-yloxypyrrolidine Chemical compound C1CCCN1ON1CCCC1 OBOOCHGOPNGGLO-UHFFFAOYSA-N 0.000 claims description 2
• QRWZFUBHOQWUGH-UHFFFAOYSA-N 2,5-dimethylpyrazole-3-carboxylic acid Chemical compound CC=1C=C(C(O)=O)N(C)N=1 QRWZFUBHOQWUGH-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• UPYUXTOZRFMXCW-UHFFFAOYSA-N 3-[3-(dimethylamino)pyrrolidin-1-yl]-n-[4-methyl-3-[(1-pyrimidin-4-ylbenzimidazol-2-yl)amino]phenyl]-5-(trifluoromethyl)benzamide Chemical compound C1C(N(C)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 UPYUXTOZRFMXCW-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• GNWMHLBUCXEXPE-UHFFFAOYSA-N 5-cyclopropyl-1h-pyrazole-3-carboxylic acid Chemical compound N1N=C(C(=O)O)C=C1C1CC1 GNWMHLBUCXEXPE-UHFFFAOYSA-N 0.000 claims description 2
• GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 2
• 101150035397 Ros1 gene Proteins 0.000 claims description 2
• MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 claims description 2
• 125000003435 aroyl group Chemical group 0.000 claims description 2
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
• 125000001207 fluorophenyl group Chemical group 0.000 claims description 2
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
• 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 2
• 125000006399 methylpyrazinyl group Chemical group 0.000 claims description 2
• 125000006393 methylpyrimidinyl group Chemical group 0.000 claims description 2
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
• OUTQAPFODIHZSQ-UHFFFAOYSA-N n-(2-chloro-6-methylphenyl)-1-[6-(4-morpholin-4-ylpiperidin-1-yl)pyrimidin-4-yl]benzimidazol-2-amine Chemical compound CC1=CC=CC(Cl)=C1NC1=NC2=CC=CC=C2N1C1=CC(N2CCC(CC2)N2CCOCC2)=NC=N1 OUTQAPFODIHZSQ-UHFFFAOYSA-N 0.000 claims description 2
• QBNFHYXLBWPRJZ-UHFFFAOYSA-N n-(2-chloro-6-methylphenyl)-1-[6-[2-(4-methylpiperazin-1-yl)ethylamino]pyrimidin-4-yl]benzimidazol-2-amine Chemical compound C1CN(C)CCN1CCNC1=CC(N2C3=CC=CC=C3N=C2NC=2C(=CC=CC=2C)Cl)=NC=N1 QBNFHYXLBWPRJZ-UHFFFAOYSA-N 0.000 claims description 2
• PICSDTONCAVDKS-UHFFFAOYSA-N n-(2-methylphenyl)-1-pyrimidin-4-ylbenzimidazol-2-amine Chemical compound CC1=CC=CC=C1NC1=NC2=CC=CC=C2N1C1=CC=NC=N1 PICSDTONCAVDKS-UHFFFAOYSA-N 0.000 claims description 2
• WGIDARPRXYQNKF-UHFFFAOYSA-N n-(4-phenoxyphenyl)-1-pyrimidin-4-ylbenzimidazol-2-amine Chemical compound C=1C=C(OC=2C=CC=CC=2)C=CC=1NC1=NC2=CC=CC=C2N1C1=CC=NC=N1 WGIDARPRXYQNKF-UHFFFAOYSA-N 0.000 claims description 2
• VXYKTIWYKXNBLX-UHFFFAOYSA-N n-[3-[[1-(6-amino-5-methylpyrimidin-4-yl)benzimidazol-2-yl]amino]-4-methylphenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(NC=2N(C3=CC=CC=C3N=2)C=2C(=C(N)N=CN=2)C)C(C)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 VXYKTIWYKXNBLX-UHFFFAOYSA-N 0.000 claims description 2
• YQPHBBQBBMIYLO-UHFFFAOYSA-N n-[3-[[1-(6-aminopyrimidin-4-yl)benzimidazol-2-yl]amino]-4-methylphenyl]-3-(4-methylpiperazin-1-yl)-5-(trifluoromethyl)benzamide Chemical compound C1CN(C)CCN1C1=CC(C(=O)NC=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 YQPHBBQBBMIYLO-UHFFFAOYSA-N 0.000 claims description 2
• OBLWMYNSTHSSDS-UHFFFAOYSA-N n-[3-[[1-(6-aminopyrimidin-4-yl)benzimidazol-2-yl]amino]-4-methylphenyl]-3-(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)C1=CC=CC(C(F)(F)F)=C1 OBLWMYNSTHSSDS-UHFFFAOYSA-N 0.000 claims description 2
• KXTIIOOGQPWWGE-UHFFFAOYSA-N n-[3-[[1-(6-aminopyrimidin-4-yl)benzimidazol-2-yl]amino]-4-methylphenyl]-3-chloro-4-[(4-ethylpiperazin-1-yl)methyl]benzamide Chemical compound C1CN(CC)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3N(C4=CC=CC=C4N=3)C=3N=CN=C(N)C=3)C(C)=CC=2)C=C1Cl KXTIIOOGQPWWGE-UHFFFAOYSA-N 0.000 claims description 2
• SOLCZUBPADGMSF-UHFFFAOYSA-N n-[3-[[1-(6-aminopyrimidin-4-yl)benzimidazol-2-yl]amino]-4-methylphenyl]-3-chlorobenzamide Chemical compound C1=C(NC=2N(C3=CC=CC=C3N=2)C=2N=CN=C(N)C=2)C(C)=CC=C1NC(=O)C1=CC=CC(Cl)=C1 SOLCZUBPADGMSF-UHFFFAOYSA-N 0.000 claims description 2
• AYZBGELVIWCHIM-UHFFFAOYSA-N n-[3-[[1-(6-aminopyrimidin-4-yl)benzimidazol-2-yl]amino]-4-methylphenyl]-3-methylbenzamide Chemical compound CC1=CC=CC(C(=O)NC=2C=C(NC=3N(C4=CC=CC=C4N=3)C=3N=CN=C(N)C=3)C(C)=CC=2)=C1 AYZBGELVIWCHIM-UHFFFAOYSA-N 0.000 claims description 2
• QJJCDXBVFBLEDI-UHFFFAOYSA-N n-[3-[[1-(6-chloro-5-methylpyrimidin-4-yl)benzimidazol-2-yl]amino]-4-methylphenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(NC=2N(C3=CC=CC=C3N=2)C=2C(=C(Cl)N=CN=2)C)C(C)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 QJJCDXBVFBLEDI-UHFFFAOYSA-N 0.000 claims description 2
• KNHQCAPUHAYVMO-UHFFFAOYSA-N n-[3-[[1-(6-chloropyrimidin-4-yl)benzimidazol-2-yl]amino]-4-methylphenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(NC=2N(C3=CC=CC=C3N=2)C=2N=CN=C(Cl)C=2)C(C)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 KNHQCAPUHAYVMO-UHFFFAOYSA-N 0.000 claims description 2
• VRMZWFNHUNLCMF-UHFFFAOYSA-N n-[3-[[1-[6-[(1-ethylpyrrolidin-2-yl)methylamino]pyrimidin-4-yl]benzimidazol-2-yl]amino]-4-methylphenyl]-3-(trifluoromethyl)benzamide Chemical compound CCN1CCCC1CNC1=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 VRMZWFNHUNLCMF-UHFFFAOYSA-N 0.000 claims description 2
• REDBMKRPRFVCHI-UHFFFAOYSA-N n-[3-[[1-[6-[2-(diethylamino)ethylamino]pyrimidin-4-yl]benzimidazol-2-yl]amino]-4-methylphenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=NC(NCCN(CC)CC)=CC(N2C3=CC=CC=C3N=C2NC=2C(=CC=C(NC(=O)C=3C=C(C=CC=3)C(F)(F)F)C=2)C)=N1 REDBMKRPRFVCHI-UHFFFAOYSA-N 0.000 claims description 2
• ZJEDGXGHFKCGDV-UHFFFAOYSA-N n-[3-[[1-[6-[4-(diethylamino)butylamino]pyrimidin-4-yl]benzimidazol-2-yl]amino]-4-methylphenyl]-3-(4-methylimidazol-1-yl)-5-(trifluoromethyl)benzamide Chemical compound C1=NC(NCCCCN(CC)CC)=CC(N2C3=CC=CC=C3N=C2NC=2C(=CC=C(NC(=O)C=3C=C(C=C(C=3)N3C=C(C)N=C3)C(F)(F)F)C=2)C)=N1 ZJEDGXGHFKCGDV-UHFFFAOYSA-N 0.000 claims description 2
• FITNUKNIUJHPPH-UHFFFAOYSA-N n-[3-[[1-[6-[4-(diethylamino)butylamino]pyrimidin-4-yl]benzimidazol-2-yl]amino]-4-methylphenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=NC(NCCCCN(CC)CC)=CC(N2C3=CC=CC=C3N=C2NC=2C(=CC=C(NC(=O)C=3C=C(C=CC=3)C(F)(F)F)C=2)C)=N1 FITNUKNIUJHPPH-UHFFFAOYSA-N 0.000 claims description 2
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