CA2729965A1 - Fused heterocyclyc inhibitor compounds - Google Patents

Info

Publication number

CA2729965A1

CA2729965A1 CA2729965A CA2729965A CA2729965A1 CA 2729965 A1 CA2729965 A1 CA 2729965A1 CA 2729965 A CA2729965 A CA 2729965A CA 2729965 A CA2729965 A CA 2729965A CA 2729965 A1 CA2729965 A1 CA 2729965A1

Authority

CA

Canada

Prior art keywords

pyrimidin

ylamino

pyridin

benzamide

hydroxy

Prior art date

2008-07-14

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

• 150000001875 compounds Chemical class 0.000 title claims abstract description 317
• 239000003112 inhibitor Substances 0.000 title description 15
• 238000000034 method Methods 0.000 claims abstract description 32
• 102000003964 Histone deacetylase Human genes 0.000 claims abstract description 29
• 108090000353 Histone deacetylase Proteins 0.000 claims abstract description 29
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 26
• 201000010099 disease Diseases 0.000 claims abstract description 24
• 230000002401 inhibitory effect Effects 0.000 claims abstract description 13
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
• -1 cyano, hydroxy Chemical group 0.000 claims description 675
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 363
• ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 claims description 187
• 125000000217 alkyl group Chemical group 0.000 claims description 118
• 150000003839 salts Chemical class 0.000 claims description 74
• 125000003118 aryl group Chemical group 0.000 claims description 62
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 56
• 125000001072 heteroaryl group Chemical group 0.000 claims description 46
• 125000001188 haloalkyl group Chemical group 0.000 claims description 45
• 125000005843 halogen group Chemical group 0.000 claims description 42
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 40
• 125000000623 heterocyclic group Chemical group 0.000 claims description 39
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 38
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 38
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 38
• 125000000304 alkynyl group Chemical group 0.000 claims description 35
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 35
• 125000001424 substituent group Chemical group 0.000 claims description 34
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
• 125000003342 alkenyl group Chemical group 0.000 claims description 30
• 229910052757 nitrogen Inorganic materials 0.000 claims description 24
• 108091007914 CDKs Proteins 0.000 claims description 23
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 23
• 229910052739 hydrogen Inorganic materials 0.000 claims description 21
• 125000001246 bromo group Chemical group Br* 0.000 claims description 16
• 125000004122 cyclic group Chemical group 0.000 claims description 16
• 125000001589 carboacyl group Chemical group 0.000 claims description 15
• GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 14
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
• 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 13
• 125000005236 alkanoylamino group Chemical group 0.000 claims description 13
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
• 239000001257 hydrogen Substances 0.000 claims description 13
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 12
• 241001465754 Metazoa Species 0.000 claims description 11
• 229910052799 carbon Inorganic materials 0.000 claims description 11
• 125000001153 fluoro group Chemical group F* 0.000 claims description 11
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 10
• 125000004423 acyloxy group Chemical group 0.000 claims description 10
• 125000006264 diethylaminomethyl group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims description 10
• 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 10
• 125000003106 haloaryl group Chemical group 0.000 claims description 10
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
• 125000005110 aryl thio group Chemical group 0.000 claims description 9
• 125000004104 aryloxy group Chemical group 0.000 claims description 9
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 9
• 125000005842 heteroatom Chemical group 0.000 claims description 9
• 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 9
• 125000004468 heterocyclylthio group Chemical group 0.000 claims description 9
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
• 125000002883 imidazolyl group Chemical group 0.000 claims description 9
• HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims description 9
• 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 9
• 125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 9
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 8
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 8
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 8
• DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical group CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 claims description 8
• 229910052717 sulfur Inorganic materials 0.000 claims description 8
• 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 7
• 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 7
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 7
• 125000004282 imidazolidin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])N([H])C1([H])* 0.000 claims description 7
• 125000004283 imidazolin-2-yl group Chemical group [H]N1C(*)=NC([H])([H])C1([H])[H] 0.000 claims description 7
• 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims description 7
• 125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 claims description 7
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 7
• 125000002912 morpholin-4-ylsulfonyl group Chemical group O1C([H])([H])C([H])([H])N(S(=O)(=O)[*])C([H])([H])C1([H])[H] 0.000 claims description 7
• 125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 claims description 7
• 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 7
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 7
• 125000004290 pyrazolidin-3-yl group Chemical group [H]N1N([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
• 125000004291 pyrazolin-3-yl group Chemical group [H]C1([H])N=NC([H])(*)C1([H])[H] 0.000 claims description 7
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
• 206010016654 Fibrosis Diseases 0.000 claims description 6
• 239000002246 antineoplastic agent Substances 0.000 claims description 6
• 230000004761 fibrosis Effects 0.000 claims description 6
• 239000003276 histone deacetylase inhibitor Substances 0.000 claims description 6
• 230000001404 mediated effect Effects 0.000 claims description 6
• 201000003883 Cystic fibrosis Diseases 0.000 claims description 5
• 230000002159 abnormal effect Effects 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 229940121372 histone deacetylase inhibitor Drugs 0.000 claims description 5
• 208000005069 pulmonary fibrosis Diseases 0.000 claims description 5
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 4
• AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims description 4
• NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 claims description 4
• 230000024245 cell differentiation Effects 0.000 claims description 4
• 230000004663 cell proliferation Effects 0.000 claims description 4
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
• HFXAVTRLAAABKN-UHFFFAOYSA-N methyl 3-[2-[4-[(2-aminophenyl)carbamoyl]anilino]pyrimidin-4-yl]-2-methylimidazo[1,2-a]pyridine-7-carboxylate Chemical compound CC=1N=C2C=C(C(=O)OC)C=CN2C=1C(N=1)=CC=NC=1NC(C=C1)=CC=C1C(=O)NC1=CC=CC=C1N HFXAVTRLAAABKN-UHFFFAOYSA-N 0.000 claims description 4
• IIAUFZVRVKRADZ-UHFFFAOYSA-N n-hydroxy-4-[(4-imidazo[1,2-a]pyridin-3-ylpyrimidin-2-yl)-(2,2,2-trifluoroethyl)amino]benzamide Chemical compound C1=CC(C(=O)NO)=CC=C1N(CC(F)(F)F)C1=NC=CC(C=2N3C=CC=CC3=NC=2)=N1 IIAUFZVRVKRADZ-UHFFFAOYSA-N 0.000 claims description 4
• 125000004043 oxo group Chemical group O=* 0.000 claims description 4
• 201000002793 renal fibrosis Diseases 0.000 claims description 4
• RCZGPTJVVPGDAY-UHFFFAOYSA-N 2-fluoro-n-hydroxy-4-[[4-(2-methylimidazo[1,2-a]pyridin-3-yl)pyrimidin-2-yl]amino]benzamide Chemical compound CC=1N=C2C=CC=CN2C=1C(N=1)=CC=NC=1NC1=CC=C(C(=O)NO)C(F)=C1 RCZGPTJVVPGDAY-UHFFFAOYSA-N 0.000 claims description 3
• CKLAVVIGLANTRR-UHFFFAOYSA-N 3-[2-[4-[(2-aminophenyl)carbamoyl]anilino]pyrimidin-4-yl]-2-methylimidazo[1,2-a]pyridine-7-carboxylic acid Chemical compound CC=1N=C2C=C(C(O)=O)C=CN2C=1C(N=1)=CC=NC=1NC(C=C1)=CC=C1C(=O)NC1=CC=CC=C1N CKLAVVIGLANTRR-UHFFFAOYSA-N 0.000 claims description 3
• MJLWHUSYADKQSS-UHFFFAOYSA-N 3-fluoro-n-hydroxy-4-[[4-(2-methylimidazo[1,2-a]pyridin-3-yl)pyrimidin-2-yl]amino]benzamide Chemical compound CC=1N=C2C=CC=CN2C=1C(N=1)=CC=NC=1NC1=CC=C(C(=O)NO)C=C1F MJLWHUSYADKQSS-UHFFFAOYSA-N 0.000 claims description 3
• GCFVULJYFNGILX-UHFFFAOYSA-N 4-[[4-(8-fluoro-2-methylimidazo[1,2-a]pyridin-3-yl)pyrimidin-2-yl]amino]-n-hydroxybenzamide Chemical compound CC=1N=C2C(F)=CC=CN2C=1C(N=1)=CC=NC=1NC1=CC=C(C(=O)NO)C=C1 GCFVULJYFNGILX-UHFFFAOYSA-N 0.000 claims description 3
• 208000024827 Alzheimer disease Diseases 0.000 claims description 3
• 229910003600 H2NS Inorganic materials 0.000 claims description 3
• NJAXVOVDENOYJX-UHFFFAOYSA-N N-hydroxy-4-[[4-(2-methylimidazo[1,2-a]pyrazin-3-yl)pyrimidin-2-yl]amino]benzamide Chemical compound CC=1N=C2C=NC=CN2C=1C(N=1)=CC=NC=1NC1=CC=C(C(=O)NO)C=C1 NJAXVOVDENOYJX-UHFFFAOYSA-N 0.000 claims description 3
• CZYYEPCVKGOOTH-UHFFFAOYSA-N N-hydroxy-4-[[4-(2-methylimidazo[1,2-b]pyridazin-3-yl)pyrimidin-2-yl]amino]benzamide Chemical compound CC=1N=C2C=CC=NN2C=1C(N=1)=CC=NC=1NC1=CC=C(C(=O)NO)C=C1 CZYYEPCVKGOOTH-UHFFFAOYSA-N 0.000 claims description 3
• BRVLHJOIGKIQCY-UHFFFAOYSA-N N-hydroxy-5-[[4-(2-methylimidazo[1,2-a]pyridin-3-yl)pyrimidin-2-yl]amino]pyrazine-2-carboxamide Chemical compound CC=1N=C2C=CC=CN2C=1C(N=1)=CC=NC=1NC1=CN=C(C(=O)NO)C=N1 BRVLHJOIGKIQCY-UHFFFAOYSA-N 0.000 claims description 3
• 206010012601 diabetes mellitus Diseases 0.000 claims description 3
• 201000001441 melanoma Diseases 0.000 claims description 3
• SSXCXXGECXXTQG-UHFFFAOYSA-N n-(2-aminophenyl)-4-[(4-imidazo[1,2-a]pyridin-3-ylpyrimidin-2-yl)-(2,2,2-trifluoroethyl)amino]benzamide Chemical compound NC1=CC=CC=C1NC(=O)C1=CC=C(N(CC(F)(F)F)C=2N=C(C=CN=2)C=2N3C=CC=CC3=NC=2)C=C1 SSXCXXGECXXTQG-UHFFFAOYSA-N 0.000 claims description 3
• LUOACHBPMBHSEC-UHFFFAOYSA-N n-(2-aminophenyl)-4-[[4-(7-cyano-2-methylimidazo[1,2-a]pyridin-3-yl)pyrimidin-2-yl]amino]benzamide Chemical compound CC=1N=C2C=C(C#N)C=CN2C=1C(N=1)=CC=NC=1NC(C=C1)=CC=C1C(=O)NC1=CC=CC=C1N LUOACHBPMBHSEC-UHFFFAOYSA-N 0.000 claims description 3
• WNAHZZNLQJXYEE-UHFFFAOYSA-N n-(2-aminophenyl)-4-[[4-[7-methoxy-2-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]amino]benzamide Chemical compound FC(F)(F)C=1N=C2C=C(OC)C=CN2C=1C(N=1)=CC=NC=1NC(C=C1)=CC=C1C(=O)NC1=CC=CC=C1N WNAHZZNLQJXYEE-UHFFFAOYSA-N 0.000 claims description 3
• OQIVZJGVLIRVLB-UHFFFAOYSA-N n-(2-aminophenyl)-5-[[4-(2-methylimidazo[1,2-a]pyridin-3-yl)pyrimidin-2-yl]amino]thiophene-3-carboxamide Chemical compound CC=1N=C2C=CC=CN2C=1C(N=1)=CC=NC=1NC(SC=1)=CC=1C(=O)NC1=CC=CC=C1N OQIVZJGVLIRVLB-UHFFFAOYSA-N 0.000 claims description 3
• SXSZRNQMGMGSEH-UHFFFAOYSA-N n-hydroxy-2-[[4-(2-methylimidazo[1,2-a]pyridin-3-yl)pyrimidin-2-yl]amino]-1,3-thiazole-4-carboxamide Chemical compound CC=1N=C2C=CC=CN2C=1C(N=1)=CC=NC=1NC1=NC(C(=O)NO)=CS1 SXSZRNQMGMGSEH-UHFFFAOYSA-N 0.000 claims description 3
• HFSMVUPGUHVSBY-UHFFFAOYSA-N n-hydroxy-3-[(4-imidazo[1,2-a]pyridin-3-ylpyrimidin-2-yl)amino]benzamide Chemical compound ONC(=O)C1=CC=CC(NC=2N=C(C=CN=2)C=2N3C=CC=CC3=NC=2)=C1 HFSMVUPGUHVSBY-UHFFFAOYSA-N 0.000 claims description 3
• IBTLQPIOUREAFC-UHFFFAOYSA-N n-hydroxy-3-[[4-(2-methylimidazo[1,2-a]pyridin-3-yl)pyrimidin-2-yl]amino]benzamide Chemical compound CC=1N=C2C=CC=CN2C=1C(N=1)=CC=NC=1NC1=CC=CC(C(=O)NO)=C1 IBTLQPIOUREAFC-UHFFFAOYSA-N 0.000 claims description 3
• YUKQHEDCOBZZTJ-UHFFFAOYSA-N n-hydroxy-4-[(4-imidazo[1,2-a]pyridin-3-ylpyrimidin-2-yl)amino]benzamide Chemical compound C1=CC(C(=O)NO)=CC=C1NC1=NC=CC(C=2N3C=CC=CC3=NC=2)=N1 YUKQHEDCOBZZTJ-UHFFFAOYSA-N 0.000 claims description 3
• RYZSOFDLVFFVBG-UHFFFAOYSA-N n-hydroxy-4-[[4-(2-methylimidazo[1,2-a]pyridin-3-yl)pyridin-2-yl]amino]benzamide Chemical compound CC=1N=C2C=CC=CN2C=1C(C=1)=CC=NC=1NC1=CC=C(C(=O)NO)C=C1 RYZSOFDLVFFVBG-UHFFFAOYSA-N 0.000 claims description 3
• NQEDBSIXJCXFRN-UHFFFAOYSA-N n-hydroxy-4-[[4-(2-methylimidazo[1,2-a]pyridin-3-yl)pyrimidin-2-yl]amino]benzamide Chemical compound CC=1N=C2C=CC=CN2C=1C(N=1)=CC=NC=1NC1=CC=C(C(=O)NO)C=C1 NQEDBSIXJCXFRN-UHFFFAOYSA-N 0.000 claims description 3
• MRTOOWAMDALRSB-UHFFFAOYSA-N n-hydroxy-4-[[4-(2-methylimidazo[1,2-a]pyrimidin-3-yl)pyrimidin-2-yl]amino]benzamide Chemical compound CC=1N=C2N=CC=CN2C=1C(N=1)=CC=NC=1NC1=CC=C(C(=O)NO)C=C1 MRTOOWAMDALRSB-UHFFFAOYSA-N 0.000 claims description 3
• SWEBAYAPUIQQFC-UHFFFAOYSA-N n-hydroxy-4-[[4-(7-methoxy-2-methylimidazo[1,2-a]pyridin-3-yl)pyrimidin-2-yl]amino]benzamide Chemical compound CC=1N=C2C=C(OC)C=CN2C=1C(N=1)=CC=NC=1NC1=CC=C(C(=O)NO)C=C1 SWEBAYAPUIQQFC-UHFFFAOYSA-N 0.000 claims description 3
• ORFAUJNHZFHEOI-UHFFFAOYSA-N n-hydroxy-4-[[4-[2-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]amino]benzamide Chemical compound C1=CC(C(=O)NO)=CC=C1NC1=NC=CC(C=2N3C=CC=CC3=NC=2C(F)(F)F)=N1 ORFAUJNHZFHEOI-UHFFFAOYSA-N 0.000 claims description 3
• BYIYRAFANZQHJQ-UHFFFAOYSA-N n-hydroxy-4-[[4-[2-methyl-6-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]amino]benzamide Chemical compound CC=1N=C2C=CC(C(F)(F)F)=CN2C=1C(N=1)=CC=NC=1NC1=CC=C(C(=O)NO)C=C1 BYIYRAFANZQHJQ-UHFFFAOYSA-N 0.000 claims description 3
• QWIFJZOAARSFLU-UHFFFAOYSA-N n-hydroxy-4-[[4-[2-methyl-7-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]amino]benzamide Chemical compound CC=1N=C2C=C(C(F)(F)F)C=CN2C=1C(N=1)=CC=NC=1NC1=CC=C(C(=O)NO)C=C1 QWIFJZOAARSFLU-UHFFFAOYSA-N 0.000 claims description 3
• CUBJKESTYOQKBS-UHFFFAOYSA-N n-hydroxy-5-[[4-(2-methylimidazo[1,2-a]pyridin-3-yl)pyrimidin-2-yl]amino]thiophene-2-carboxamide Chemical compound CC=1N=C2C=CC=CN2C=1C(N=1)=CC=NC=1NC1=CC=C(C(=O)NO)S1 CUBJKESTYOQKBS-UHFFFAOYSA-N 0.000 claims description 3
• DYKDWRFGVDYXAL-UHFFFAOYSA-N n-hydroxy-6-[[4-(2-methylimidazo[1,2-a]pyridin-3-yl)pyridin-2-yl]amino]pyridine-3-carboxamide Chemical compound CC=1N=C2C=CC=CN2C=1C(C=1)=CC=NC=1NC1=CC=C(C(=O)NO)C=N1 DYKDWRFGVDYXAL-UHFFFAOYSA-N 0.000 claims description 3
• 229910052760 oxygen Inorganic materials 0.000 claims description 3
• 230000002062 proliferating effect Effects 0.000 claims description 3
• 125000006413 ring segment Chemical group 0.000 claims description 3
• FDKXTQMXEQVLRF-ZHACJKMWSA-N (E)-dacarbazine Chemical compound CN(C)\N=N\c1[nH]cnc1C(N)=O FDKXTQMXEQVLRF-ZHACJKMWSA-N 0.000 claims description 2
• GQGDZENKAOBWJR-UHFFFAOYSA-N 3-[2-[4-[(2-aminophenyl)carbamoyl]anilino]pyrimidin-4-yl]-2-methyl-n-(2-morpholin-4-ylethyl)imidazo[1,2-a]pyridine-6-carboxamide Chemical compound CC=1N=C2C=CC(C(=O)NCCN3CCOCC3)=CN2C=1C(N=1)=CC=NC=1NC(C=C1)=CC=C1C(=O)NC1=CC=CC=C1N GQGDZENKAOBWJR-UHFFFAOYSA-N 0.000 claims description 2
• VEDFXADQRYSFBW-UHFFFAOYSA-N 3-[2-[4-[(2-aminophenyl)carbamoyl]anilino]pyrimidin-4-yl]-2-methyl-n-(2-morpholin-4-ylethyl)imidazo[1,2-a]pyridine-7-carboxamide Chemical compound CC=1N=C2C=C(C(=O)NCCN3CCOCC3)C=CN2C=1C(N=1)=CC=NC=1NC(C=C1)=CC=C1C(=O)NC1=CC=CC=C1N VEDFXADQRYSFBW-UHFFFAOYSA-N 0.000 claims description 2
• DAWDFYSVFPONIF-UHFFFAOYSA-N 3-[2-[4-[(2-aminophenyl)carbamoyl]anilino]pyrimidin-4-yl]-n-(2-methoxyethyl)-2-methylimidazo[1,2-a]pyridine-6-carboxamide Chemical compound N12C=C(C(=O)NCCOC)C=CC2=NC(C)=C1C(N=1)=CC=NC=1NC(C=C1)=CC=C1C(=O)NC1=CC=CC=C1N DAWDFYSVFPONIF-UHFFFAOYSA-N 0.000 claims description 2
• RIGBYBCOVJYBBY-UHFFFAOYSA-N 3-[2-[4-[(2-aminophenyl)carbamoyl]anilino]pyrimidin-4-yl]-n-[2-(dimethylamino)ethyl]-2-methylimidazo[1,2-a]pyridine-6-carboxamide Chemical compound N12C=C(C(=O)NCCN(C)C)C=CC2=NC(C)=C1C(N=1)=CC=NC=1NC(C=C1)=CC=C1C(=O)NC1=CC=CC=C1N RIGBYBCOVJYBBY-UHFFFAOYSA-N 0.000 claims description 2
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• ZKZPVSBYOBNWTC-UHFFFAOYSA-N n-(2-aminophenyl)-4-[[4-[2-methyl-6-(trifluoromethyl)imidazo[1,2-a]pyrimidin-3-yl]pyrimidin-2-yl]amino]benzamide Chemical compound CC=1N=C2N=CC(C(F)(F)F)=CN2C=1C(N=1)=CC=NC=1NC(C=C1)=CC=C1C(=O)NC1=CC=CC=C1N ZKZPVSBYOBNWTC-UHFFFAOYSA-N 0.000 claims 1
• FJRPFPCPVOKMFH-UHFFFAOYSA-N n-(2-aminophenyl)-4-[[4-[2-methyl-6-(trifluoromethyl)imidazo[1,2-b]pyridazin-3-yl]pyrimidin-2-yl]amino]benzamide Chemical compound CC=1N=C2C=CC(C(F)(F)F)=NN2C=1C(N=1)=CC=NC=1NC(C=C1)=CC=C1C(=O)NC1=CC=CC=C1N FJRPFPCPVOKMFH-UHFFFAOYSA-N 0.000 claims 1
• FFIWFDUJIGOCJL-UHFFFAOYSA-N n-(2-aminophenyl)-4-[[4-[2-methyl-7-(trifluoromethyl)imidazo[1,2-a]pyrimidin-3-yl]pyrimidin-2-yl]amino]benzamide Chemical compound CC=1N=C2N=C(C(F)(F)F)C=CN2C=1C(N=1)=CC=NC=1NC(C=C1)=CC=C1C(=O)NC1=CC=CC=C1N FFIWFDUJIGOCJL-UHFFFAOYSA-N 0.000 claims 1
• RNHNJZPLWVJRBM-UHFFFAOYSA-N n-(2-aminophenyl)-4-[[4-[2-methyl-7-(trifluoromethyl)imidazo[1,2-b]pyridazin-3-yl]pyrimidin-2-yl]amino]benzamide Chemical compound CC=1N=C2C=C(C(F)(F)F)C=NN2C=1C(N=1)=CC=NC=1NC(C=C1)=CC=C1C(=O)NC1=CC=CC=C1N RNHNJZPLWVJRBM-UHFFFAOYSA-N 0.000 claims 1
• KZSWHLZICAZYER-UHFFFAOYSA-N n-(2-aminophenyl)-4-[[4-[2-methyl-7-(trifluoromethyl)imidazo[1,2-c]pyrimidin-3-yl]pyrimidin-2-yl]amino]benzamide Chemical compound CC=1N=C2C=C(C(F)(F)F)N=CN2C=1C(N=1)=CC=NC=1NC(C=C1)=CC=C1C(=O)NC1=CC=CC=C1N KZSWHLZICAZYER-UHFFFAOYSA-N 0.000 claims 1
• AUJLMDCXNYDWPI-UHFFFAOYSA-N n-(2-aminophenyl)-4-[[4-[7-(morpholin-4-ylmethyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]amino]benzamide Chemical compound NC1=CC=CC=C1NC(=O)C(C=C1)=CC=C1NC1=NC=CC(C=2N3C=CC(CN4CCOCC4)=CC3=NC=2)=N1 AUJLMDCXNYDWPI-UHFFFAOYSA-N 0.000 claims 1
• XTEVQCXQXCXRKN-UHFFFAOYSA-N n-(2-aminophenyl)-4-[[4-[7-(pyrrolidin-1-ylmethyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]amino]benzamide Chemical compound NC1=CC=CC=C1NC(=O)C(C=C1)=CC=C1NC1=NC=CC(C=2N3C=CC(CN4CCCC4)=CC3=NC=2)=N1 XTEVQCXQXCXRKN-UHFFFAOYSA-N 0.000 claims 1
• JIVHQCKENCEAMQ-UHFFFAOYSA-N n-(2-aminophenyl)-4-[[4-[7-[(dimethylamino)methyl]imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]amino]benzamide Chemical compound C=1N=C2C=C(CN(C)C)C=CN2C=1C(N=1)=CC=NC=1NC(C=C1)=CC=C1C(=O)NC1=CC=CC=C1N JIVHQCKENCEAMQ-UHFFFAOYSA-N 0.000 claims 1
• CJAPRZNQRQMMEX-UHFFFAOYSA-N n-(2-aminophenyl)-4-[[4-[7-methoxy-2-(trifluoromethyl)imidazo[1,2-a]pyrimidin-3-yl]pyrimidin-2-yl]amino]benzamide Chemical compound FC(F)(F)C=1N=C2N=C(OC)C=CN2C=1C(N=1)=CC=NC=1NC(C=C1)=CC=C1C(=O)NC1=CC=CC=C1N CJAPRZNQRQMMEX-UHFFFAOYSA-N 0.000 claims 1
• BETAFIZHOBUQPR-UHFFFAOYSA-N n-(2-aminophenyl)-4-[[4-[7-methoxy-2-(trifluoromethyl)imidazo[1,2-b]pyridazin-3-yl]pyrimidin-2-yl]amino]benzamide Chemical compound FC(F)(F)C=1N=C2C=C(OC)C=NN2C=1C(N=1)=CC=NC=1NC(C=C1)=CC=C1C(=O)NC1=CC=CC=C1N BETAFIZHOBUQPR-UHFFFAOYSA-N 0.000 claims 1
• LKDYWQVZNVDARN-UHFFFAOYSA-N n-(2-aminophenyl)-4-[[4-[7-methoxy-2-(trifluoromethyl)imidazo[1,2-c]pyrimidin-3-yl]pyrimidin-2-yl]amino]benzamide Chemical compound N12C=NC(OC)=CC2=NC(C(F)(F)F)=C1C(N=1)=CC=NC=1NC(C=C1)=CC=C1C(=O)NC1=CC=CC=C1N LKDYWQVZNVDARN-UHFFFAOYSA-N 0.000 claims 1
• AMKPHNSVLITDFP-UHFFFAOYSA-N n-(2-aminophenyl)-4-[[5-methyl-4-(2-methylimidazo[1,2-a]pyridin-3-yl)pyrimidin-2-yl]amino]benzamide Chemical compound CC=1N=C2C=CC=CN2C=1C(C(=CN=1)C)=NC=1NC(C=C1)=CC=C1C(=O)NC1=CC=CC=C1N AMKPHNSVLITDFP-UHFFFAOYSA-N 0.000 claims 1
• KRNITKKQJADPJQ-UHFFFAOYSA-N n-(2-aminophenyl)-4-[ethyl-(4-imidazo[1,2-a]pyridin-3-ylpyrimidin-2-yl)amino]benzamide Chemical compound N=1C=CC(C=2N3C=CC=CC3=NC=2)=NC=1N(CC)C(C=C1)=CC=C1C(=O)NC1=CC=CC=C1N KRNITKKQJADPJQ-UHFFFAOYSA-N 0.000 claims 1
• YAGVZJKPQIQUQJ-UHFFFAOYSA-N n-(2-aminophenyl)-5-[(4-imidazo[1,2-a]pyridin-3-ylpyrimidin-2-yl)amino]thiophene-2-carboxamide Chemical compound NC1=CC=CC=C1NC(=O)C(S1)=CC=C1NC1=NC=CC(C=2N3C=CC=CC3=NC=2)=N1 YAGVZJKPQIQUQJ-UHFFFAOYSA-N 0.000 claims 1
• OBGHQWOERNGKNY-UHFFFAOYSA-N n-(2-aminophenyl)-5-[[4-(7-methoxy-2-methylimidazo[1,2-a]pyridin-3-yl)pyrimidin-2-yl]amino]thiophene-2-carboxamide Chemical compound CC=1N=C2C=C(OC)C=CN2C=1C(N=1)=CC=NC=1NC(S1)=CC=C1C(=O)NC1=CC=CC=C1N OBGHQWOERNGKNY-UHFFFAOYSA-N 0.000 claims 1
• APTJUZLVLQLNLW-UHFFFAOYSA-N n-(2-aminophenyl)-5-[[4-[2-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]amino]thiophene-2-carboxamide Chemical compound NC1=CC=CC=C1NC(=O)C(S1)=CC=C1NC1=NC=CC(C=2N3C=CC=CC3=NC=2C(F)(F)F)=N1 APTJUZLVLQLNLW-UHFFFAOYSA-N 0.000 claims 1
• YRIGLIALPXREBI-UHFFFAOYSA-N n-(2-aminophenyl)-5-[[4-[2-methyl-6-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]amino]thiophene-2-carboxamide Chemical compound CC=1N=C2C=CC(C(F)(F)F)=CN2C=1C(N=1)=CC=NC=1NC(S1)=CC=C1C(=O)NC1=CC=CC=C1N YRIGLIALPXREBI-UHFFFAOYSA-N 0.000 claims 1
• WCRKFDNOVCAKBF-UHFFFAOYSA-N n-(2-aminophenyl)-5-[[4-[2-methyl-7-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]amino]thiophene-2-carboxamide Chemical compound CC=1N=C2C=C(C(F)(F)F)C=CN2C=1C(N=1)=CC=NC=1NC(S1)=CC=C1C(=O)NC1=CC=CC=C1N WCRKFDNOVCAKBF-UHFFFAOYSA-N 0.000 claims 1
• DASDJWQXDBNCCB-UHFFFAOYSA-N n-(2-aminophenyl)-5-[[4-[7-methoxy-2-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]amino]thiophene-2-carboxamide Chemical compound FC(F)(F)C=1N=C2C=C(OC)C=CN2C=1C(N=1)=CC=NC=1NC(S1)=CC=C1C(=O)NC1=CC=CC=C1N DASDJWQXDBNCCB-UHFFFAOYSA-N 0.000 claims 1
• ZZIRARNNXPVTHA-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-3-[2-[4-(hydroxycarbamoyl)anilino]pyrimidin-4-yl]-2-methylimidazo[1,2-a]pyridine-6-carboxamide Chemical compound N12C=C(C(=O)NCCN(C)C)C=CC2=NC(C)=C1C(N=1)=CC=NC=1NC1=CC=C(C(=O)NO)C=C1 ZZIRARNNXPVTHA-UHFFFAOYSA-N 0.000 claims 1
• GPKLWCPSTNWWLU-UHFFFAOYSA-N n-hydroxy-3-[(4-imidazo[1,2-a]pyridin-3-yl-5-methylpyrimidin-2-yl)amino]benzamide Chemical compound N1=C(C=2N3C=CC=CC3=NC=2)C(C)=CN=C1NC1=CC=CC(C(=O)NO)=C1 GPKLWCPSTNWWLU-UHFFFAOYSA-N 0.000 claims 1
• OIVKKXZJWYHSRW-UHFFFAOYSA-N n-hydroxy-3-[[5-methyl-4-(2-methylimidazo[1,2-a]pyridin-3-yl)pyrimidin-2-yl]amino]benzamide Chemical compound CC=1N=C2C=CC=CN2C=1C(C(=CN=1)C)=NC=1NC1=CC=CC(C(=O)NO)=C1 OIVKKXZJWYHSRW-UHFFFAOYSA-N 0.000 claims 1
• CJXYAMFTNNKZRH-UHFFFAOYSA-N n-hydroxy-4-[(4-imidazo[1,2-a]pyridin-3-yl-1,3,5-triazin-2-yl)amino]benzamide Chemical compound C1=CC(C(=O)NO)=CC=C1NC1=NC=NC(C=2N3C=CC=CC3=NC=2)=N1 CJXYAMFTNNKZRH-UHFFFAOYSA-N 0.000 claims 1
• PPGUHEGNTLSXLQ-UHFFFAOYSA-N n-hydroxy-4-[(4-imidazo[1,2-a]pyridin-3-yl-5-methylpyrimidin-2-yl)amino]benzamide Chemical compound N1=C(C=2N3C=CC=CC3=NC=2)C(C)=CN=C1NC1=CC=C(C(=O)NO)C=C1 PPGUHEGNTLSXLQ-UHFFFAOYSA-N 0.000 claims 1
• FILNIFFQNNORKL-UHFFFAOYSA-N n-hydroxy-4-[(4-imidazo[1,2-a]pyridin-3-ylpyrimidin-2-yl)-methylamino]benzamide Chemical compound N=1C=CC(C=2N3C=CC=CC3=NC=2)=NC=1N(C)C1=CC=C(C(=O)NO)C=C1 FILNIFFQNNORKL-UHFFFAOYSA-N 0.000 claims 1
• VQMYYMFBHANAMF-UHFFFAOYSA-N n-hydroxy-4-[(4-imidazo[1,2-a]pyrimidin-3-ylpyrimidin-2-yl)amino]benzamide Chemical compound C1=CC(C(=O)NO)=CC=C1NC1=NC=CC(C=2N3C=CC=NC3=NC=2)=N1 VQMYYMFBHANAMF-UHFFFAOYSA-N 0.000 claims 1
• GVOLVBGVPAOERV-UHFFFAOYSA-N n-hydroxy-4-[(4-imidazo[1,2-c]pyrimidin-3-ylpyrimidin-2-yl)amino]benzamide Chemical compound C1=CC(C(=O)NO)=CC=C1NC1=NC=CC(C=2N3C=NC=CC3=NC=2)=N1 GVOLVBGVPAOERV-UHFFFAOYSA-N 0.000 claims 1
• HZUYOTPWHILYNN-UHFFFAOYSA-N n-hydroxy-4-[[4-(2-methylimidazo[1,2-c]pyrimidin-3-yl)pyrimidin-2-yl]amino]benzamide Chemical compound CC=1N=C2C=CN=CN2C=1C(N=1)=CC=NC=1NC1=CC=C(C(=O)NO)C=C1 HZUYOTPWHILYNN-UHFFFAOYSA-N 0.000 claims 1
• BPMHBZKHPSUCOA-UHFFFAOYSA-N n-hydroxy-4-[[4-(7-methoxy-2-methylimidazo[1,2-a]pyrimidin-3-yl)pyrimidin-2-yl]amino]benzamide Chemical compound CC=1N=C2N=C(OC)C=CN2C=1C(N=1)=CC=NC=1NC1=CC=C(C(=O)NO)C=C1 BPMHBZKHPSUCOA-UHFFFAOYSA-N 0.000 claims 1
• XFMFLZNRDHDVBR-UHFFFAOYSA-N n-hydroxy-4-[[4-(7-methoxy-2-methylimidazo[1,2-c]pyrimidin-3-yl)pyrimidin-2-yl]amino]benzamide Chemical compound N12C=NC(OC)=CC2=NC(C)=C1C(N=1)=CC=NC=1NC1=CC=C(C(=O)NO)C=C1 XFMFLZNRDHDVBR-UHFFFAOYSA-N 0.000 claims 1
• OZQUNCHFQFCUKX-UHFFFAOYSA-N n-hydroxy-4-[[4-[2-methyl-6-(4-methylpiperazine-1-carbonyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]amino]benzamide Chemical compound C1CN(C)CCN1C(=O)C1=CN2C(C=3N=C(NC=4C=CC(=CC=4)C(=O)NO)N=CC=3)=C(C)N=C2C=C1 OZQUNCHFQFCUKX-UHFFFAOYSA-N 0.000 claims 1
• AXOHORXTTRVDJT-UHFFFAOYSA-N n-hydroxy-4-[[4-[2-methyl-6-(trifluoromethyl)imidazo[1,2-a]pyrimidin-3-yl]pyrimidin-2-yl]amino]benzamide Chemical compound CC=1N=C2N=CC(C(F)(F)F)=CN2C=1C(N=1)=CC=NC=1NC1=CC=C(C(=O)NO)C=C1 AXOHORXTTRVDJT-UHFFFAOYSA-N 0.000 claims 1
• SNUYBIBLTBWLCR-UHFFFAOYSA-N n-hydroxy-4-[[4-[2-methyl-7-(2-morpholin-4-ylethoxy)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]amino]benzamide Chemical compound C1=CN2C(C=3N=C(NC=4C=CC(=CC=4)C(=O)NO)N=CC=3)=C(C)N=C2C=C1OCCN1CCOCC1 SNUYBIBLTBWLCR-UHFFFAOYSA-N 0.000 claims 1
• KDKJKTISKKBCOC-UHFFFAOYSA-N n-hydroxy-4-[[4-[2-methyl-7-(4-methylpiperazine-1-carbonyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]amino]benzamide Chemical compound C1CN(C)CCN1C(=O)C1=CC2=NC(C)=C(C=3N=C(NC=4C=CC(=CC=4)C(=O)NO)N=CC=3)N2C=C1 KDKJKTISKKBCOC-UHFFFAOYSA-N 0.000 claims 1
• JERFLMLAYYWWSH-UHFFFAOYSA-N n-hydroxy-4-[[4-[2-methyl-7-(trifluoromethyl)imidazo[1,2-a]pyrimidin-3-yl]pyrimidin-2-yl]amino]benzamide Chemical compound CC=1N=C2N=C(C(F)(F)F)C=CN2C=1C(N=1)=CC=NC=1NC1=CC=C(C(=O)NO)C=C1 JERFLMLAYYWWSH-UHFFFAOYSA-N 0.000 claims 1
• YSYLBAHOFUQBBO-UHFFFAOYSA-N n-hydroxy-4-[[4-[2-methyl-7-(trifluoromethyl)imidazo[1,2-c]pyrimidin-3-yl]pyrimidin-2-yl]amino]benzamide Chemical compound CC=1N=C2C=C(C(F)(F)F)N=CN2C=1C(N=1)=CC=NC=1NC1=CC=C(C(=O)NO)C=C1 YSYLBAHOFUQBBO-UHFFFAOYSA-N 0.000 claims 1
• FRWKEHDAUGGNKM-UHFFFAOYSA-N n-hydroxy-4-[[4-[6-(2-methoxyethoxy)-2-methylimidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]amino]benzamide Chemical compound N12C=C(OCCOC)C=CC2=NC(C)=C1C(N=1)=CC=NC=1NC1=CC=C(C(=O)NO)C=C1 FRWKEHDAUGGNKM-UHFFFAOYSA-N 0.000 claims 1
• SIIDBIZZXMZTMZ-UHFFFAOYSA-N n-hydroxy-4-[[4-[7-(2-methoxyethoxy)-2-methylimidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]amino]benzamide Chemical compound CC=1N=C2C=C(OCCOC)C=CN2C=1C(N=1)=CC=NC=1NC1=CC=C(C(=O)NO)C=C1 SIIDBIZZXMZTMZ-UHFFFAOYSA-N 0.000 claims 1
• YHSKOKRHHMBPRO-UHFFFAOYSA-N n-hydroxy-4-[[4-[7-(morpholin-4-ylmethyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]amino]benzamide Chemical compound C1=CC(C(=O)NO)=CC=C1NC1=NC=CC(C=2N3C=CC(CN4CCOCC4)=CC3=NC=2)=N1 YHSKOKRHHMBPRO-UHFFFAOYSA-N 0.000 claims 1
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• ICWXJZZHILVIHR-UHFFFAOYSA-N n-hydroxy-4-[[4-[7-methoxy-2-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]amino]benzamide Chemical compound FC(F)(F)C=1N=C2C=C(OC)C=CN2C=1C(N=1)=CC=NC=1NC1=CC=C(C(=O)NO)C=C1 ICWXJZZHILVIHR-UHFFFAOYSA-N 0.000 claims 1
• OYCYCFMRBGRALV-UHFFFAOYSA-N n-hydroxy-4-[[4-[7-methoxy-2-(trifluoromethyl)imidazo[1,2-a]pyrimidin-3-yl]pyrimidin-2-yl]amino]benzamide Chemical compound FC(F)(F)C=1N=C2N=C(OC)C=CN2C=1C(N=1)=CC=NC=1NC1=CC=C(C(=O)NO)C=C1 OYCYCFMRBGRALV-UHFFFAOYSA-N 0.000 claims 1
• WUJSILOFWCIWPG-UHFFFAOYSA-N n-hydroxy-4-[[4-[7-methoxy-2-(trifluoromethyl)imidazo[1,2-c]pyrimidin-3-yl]pyrimidin-2-yl]amino]benzamide Chemical compound N12C=NC(OC)=CC2=NC(C(F)(F)F)=C1C(N=1)=CC=NC=1NC1=CC=C(C(=O)NO)C=C1 WUJSILOFWCIWPG-UHFFFAOYSA-N 0.000 claims 1
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• FKXQSTLMJBTRNL-UHFFFAOYSA-N n-hydroxy-5-[[4-(2-methylimidazo[1,2-a]pyridin-3-yl)pyridin-2-yl]amino]-1,3,4-thiadiazole-2-carboxamide Chemical compound CC=1N=C2C=CC=CN2C=1C(C=1)=CC=NC=1NC1=NN=C(C(=O)NO)S1 FKXQSTLMJBTRNL-UHFFFAOYSA-N 0.000 claims 1
• ORNBMZZWEALKOA-UHFFFAOYSA-N n-hydroxy-5-[[4-(7-methoxy-2-methylimidazo[1,2-a]pyridin-3-yl)pyrimidin-2-yl]amino]thiophene-2-carboxamide Chemical compound CC=1N=C2C=C(OC)C=CN2C=1C(N=1)=CC=NC=1NC1=CC=C(C(=O)NO)S1 ORNBMZZWEALKOA-UHFFFAOYSA-N 0.000 claims 1
• QLQPOALNORXTQG-UHFFFAOYSA-N n-hydroxy-5-[[4-[2-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]amino]thiophene-2-carboxamide Chemical compound S1C(C(=O)NO)=CC=C1NC1=NC=CC(C=2N3C=CC=CC3=NC=2C(F)(F)F)=N1 QLQPOALNORXTQG-UHFFFAOYSA-N 0.000 claims 1
• RAVFJVYPVWFUSH-UHFFFAOYSA-N n-hydroxy-5-[[4-[2-methyl-6-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]amino]thiophene-2-carboxamide Chemical compound CC=1N=C2C=CC(C(F)(F)F)=CN2C=1C(N=1)=CC=NC=1NC1=CC=C(C(=O)NO)S1 RAVFJVYPVWFUSH-UHFFFAOYSA-N 0.000 claims 1
• RBHQZPUTGSNDLK-UHFFFAOYSA-N n-hydroxy-5-[[4-[2-methyl-7-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]amino]thiophene-2-carboxamide Chemical compound CC=1N=C2C=C(C(F)(F)F)C=CN2C=1C(N=1)=CC=NC=1NC1=CC=C(C(=O)NO)S1 RBHQZPUTGSNDLK-UHFFFAOYSA-N 0.000 claims 1
• AZPIRDBHURSMPA-UHFFFAOYSA-N n-hydroxy-5-[[4-[7-methoxy-2-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]amino]thiophene-2-carboxamide Chemical compound FC(F)(F)C=1N=C2C=C(OC)C=CN2C=1C(N=1)=CC=NC=1NC1=CC=C(C(=O)NO)S1 AZPIRDBHURSMPA-UHFFFAOYSA-N 0.000 claims 1
• OPYHDWRMSZUFEN-UHFFFAOYSA-N n-hydroxy-6-[[4-(7-methoxy-2-methylimidazo[1,2-a]pyridin-3-yl)pyridin-2-yl]amino]pyridine-3-carboxamide Chemical compound CC=1N=C2C=C(OC)C=CN2C=1C(C=1)=CC=NC=1NC1=CC=C(C(=O)NO)C=N1 OPYHDWRMSZUFEN-UHFFFAOYSA-N 0.000 claims 1
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