CA2729965A1 - Fused heterocyclyc inhibitor compounds - Google Patents
Fused heterocyclyc inhibitor compounds Download PDFInfo
- 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
- 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
- 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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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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Landscapes
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8044908P | 2008-07-14 | 2008-07-14 | |
| US61/080,449 | 2008-07-14 | ||
| PCT/US2009/050577 WO2010009155A2 (en) | 2008-07-14 | 2009-07-14 | Fused heterocyclyc inhibitor compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2729965A1 true CA2729965A1 (en) | 2010-01-21 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2729965A Abandoned CA2729965A1 (en) | 2008-07-14 | 2009-07-14 | Fused heterocyclyc inhibitor compounds |
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| Country | Link |
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| US (1) | US8124764B2 (enExample) |
| EP (1) | EP2303881A2 (enExample) |
| JP (2) | JP5640006B2 (enExample) |
| AU (1) | AU2009271019A1 (enExample) |
| CA (1) | CA2729965A1 (enExample) |
| NZ (2) | NZ590320A (enExample) |
| WO (1) | WO2010009155A2 (enExample) |
Families Citing this family (97)
| Publication number | Priority date | Publication date | Assignee | Title |
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| EP2170882A1 (en) * | 2007-06-26 | 2010-04-07 | Gilead Colorado, Inc. | Imidazopyridinyl thiazolyl histone deacetylase inhibitors |
| TW200922564A (en) | 2007-09-10 | 2009-06-01 | Curis Inc | CDK inhibitors containing a zinc binding moiety |
| JP5640005B2 (ja) | 2008-07-14 | 2014-12-10 | ギリアード サイエンシーズ， インコーポレイテッド | Ｈｄａｃおよび／またはｃｄｋ阻害剤としてのイミダゾシルピリジン化合物 |
| EP2303841A1 (en) * | 2008-07-14 | 2011-04-06 | Gilead Sciences, Inc. | Oxindolyl inhibitor compounds |
| CA2729965A1 (en) | 2008-07-14 | 2010-01-21 | Gilead Sciences, Inc. | Fused heterocyclyc inhibitor compounds |
| KR20110038159A (ko) * | 2008-07-28 | 2011-04-13 | 길리애드 사이언시즈, 인코포레이티드 | 사이클로알킬리덴 및 헤테로사이클로알킬리덴 히스톤 데아세틸라아제 억제제 화합물 |
| CA2735593C (en) | 2008-09-03 | 2017-08-15 | Repligen Corporation | Compositions including 6-aminohexanoic acid derivatives as hdac inhibitors |
| EP4585589A3 (en) * | 2008-12-03 | 2025-11-19 | The Scripps Research Institute | Stem cell cultures |
| WO2010075542A1 (en) | 2008-12-23 | 2010-07-01 | Curis, Inc. | Cdk inhibitors |
| CA2763167A1 (en) * | 2009-06-08 | 2010-12-16 | Gilead Sciences, Inc. | Cycloalkylcarbamate benzamide aniline hdac inhibitor compounds |
| AU2010259035A1 (en) | 2009-06-08 | 2011-12-08 | Gilead Sciences, Inc. | Alkanoylamino benzamide aniline HDAC inhibitor compounds |
| EP2475428B1 (en) | 2009-09-11 | 2015-07-01 | Probiodrug AG | Heterocylcic derivatives as inhibitors of glutaminyl cyclase |
| NZ599597A (en) | 2009-10-30 | 2013-05-31 | Janssen Pharmaceutica Nv | IMIDAZO[1,2-b]PYRIDAZINE DERIVATIVES AND THEIR USE AS PDE10 INHIBITORS |
| AR080754A1 (es) | 2010-03-09 | 2012-05-09 | Janssen Pharmaceutica Nv | Derivados de imidazo (1,2-a) pirazina y su uso como inhibidores de pde10 |
| JP6041808B2 (ja) * | 2010-11-16 | 2016-12-14 | アセチロン ファーマシューティカルズ インコーポレイテッドＡｃｅｔｙｌｏｎ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ，Ｉｎｃ． | 蛋白質脱アセチル化酵素抑制剤としてのピリミジン水酸基アミド化合物およびその利用方法 |
| WO2012088266A2 (en) | 2010-12-22 | 2012-06-28 | Incyte Corporation | Substituted imidazopyridazines and benzimidazoles as inhibitors of fgfr3 |
| US10059723B2 (en) | 2011-02-28 | 2018-08-28 | Biomarin Pharmaceutical Inc. | Histone deacetylase inhibitors |
| EP2680694B1 (en) | 2011-02-28 | 2019-01-02 | BioMarin Pharmaceutical Inc. | Histone deacetylase inhibitors |
| US8957066B2 (en) | 2011-02-28 | 2015-02-17 | Biomarin Pharmaceutical Inc. | Histone deacetylase inhibitors |
| CN103562184B (zh) | 2011-03-02 | 2016-04-27 | 利德探索中心有限公司 | 药学活性的二取代的吡啶衍生物 |
| EP2680852A1 (en) * | 2011-03-02 | 2014-01-08 | Lead Discovery Center GmbH | Pharmaceutically active disubstituted triazine derivatives |
| JP5912172B2 (ja) | 2011-04-19 | 2016-04-27 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | 置換された４−アリール−ｎ−フェニル−１，３，５−トリアジン−２−アミン |
| TWI555737B (zh) | 2011-05-24 | 2016-11-01 | 拜耳知識產權公司 | 含有硫醯亞胺基團之４－芳基－ｎ－苯基－１，３，５－三氮雜苯－２－胺 |
| ES2575092T3 (es) | 2011-06-27 | 2016-06-24 | Janssen Pharmaceutica, N.V. | Derivados de 1-aril-4-metil-[1,2,4]triazolo[4,3-a]quinoxalina |
| US9108926B2 (en) | 2011-09-16 | 2015-08-18 | Bayer Intellectual Property Gmbh | Disubstituted 5-fluoro-pyrimidines |
| US9133171B2 (en) | 2011-09-16 | 2015-09-15 | Bayer Intellectual Property Gmbh | Disubstituted 5-fluoro pyrimidine derivatives containing a sulfoximine group |
| CN104245680B (zh) * | 2012-04-27 | 2016-11-23 | 卫材R&D管理有限公司 | 用于生产5-(二氟甲基)吡嗪-2-甲酸的方法及其生产中间体 |
| SI2861595T1 (sl) | 2012-06-13 | 2017-04-26 | Incyte Holdings Corporation | Substituirane triciklične spojine kot inhibitorji fgfr |
| RU2657540C2 (ru) | 2012-06-26 | 2018-06-14 | Янссен Фармацевтика Нв | Комбинации, содержащие ингибиторы pde 2, такие как 1-арил-4-метил-[1,2,4]триазоло[4,3-а]хиноксалиновые соединения, и ингибиторы pde 10, для применения в лечении неврологических или метаболических расстройств |
| KR102171706B1 (ko) | 2012-07-09 | 2020-10-30 | 얀센 파마슈티카 엔.브이. | 포스포디에스테라아제 10 효소의 억제제 |
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| WO2014060375A2 (en) | 2012-10-18 | 2014-04-24 | Bayer Pharma Aktiengesellschaft | 5-fluoro-n-(pyridin-2-yl)pyridin-2-amine derivatives containing a sulfone group |
| HK1213890A1 (zh) | 2012-10-18 | 2016-07-15 | Bayer Pharma Aktiengesellschaft | 含碸基团的4-(邻)-氟苯基-5-氟嘧啶-2-基胺 |
| TW201418243A (zh) | 2012-11-15 | 2014-05-16 | Bayer Pharma AG | 含有磺醯亞胺基團之ｎ－（吡啶－２－基）嘧啶－４－胺衍生物 |
| US9266892B2 (en) | 2012-12-19 | 2016-02-23 | Incyte Holdings Corporation | Fused pyrazoles as FGFR inhibitors |
| MX370142B (es) | 2013-03-15 | 2019-12-03 | Biomarin Pharm Inc | Inhibidores de hdac. |
| LT2986610T (lt) | 2013-04-19 | 2018-04-10 | Incyte Holdings Corporation | Bicikliniai heterociklai, kaip fgfr inhibitoriai |
| US9403779B2 (en) | 2013-10-08 | 2016-08-02 | Acetylon Pharmaceuticals, Inc. | Combinations of histone deacetylase inhibitors and either Her2 inhibitors or PI3K inhibitors |
| EP3055299B1 (en) | 2013-10-10 | 2021-01-06 | Acetylon Pharmaceuticals, Inc. | Pyrimidine hydroxy amide compounds as histone deacetylase inhibitors |
| JP2016534069A (ja) | 2013-10-24 | 2016-11-04 | メイヨ・ファウンデーション・フォー・メディカル・エデュケーション・アンド・リサーチ | Ｈｄａｃ６阻害剤での多嚢胞性疾患の治療 |
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| GB201321736D0 (en) * | 2013-12-09 | 2014-01-22 | Ucb Pharma Sa | Therapeutic agents |
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| EP3166603B1 (en) | 2014-07-07 | 2020-02-12 | Acetylon Pharmaceuticals, Inc. | Treatment of leukemia with histone deacetylase inhibitors |
| CN107207475A (zh) | 2014-10-16 | 2017-09-26 | 拜耳医药股份有限公司 | 含有砜基团的氟化苯并呋喃基‑嘧啶衍生物 |
| US10851105B2 (en) | 2014-10-22 | 2020-12-01 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
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| EP2170882A1 (en) | 2007-06-26 | 2010-04-07 | Gilead Colorado, Inc. | Imidazopyridinyl thiazolyl histone deacetylase inhibitors |
| CA2729965A1 (en) | 2008-07-14 | 2010-01-21 | Gilead Sciences, Inc. | Fused heterocyclyc inhibitor compounds |
| JP5640005B2 (ja) | 2008-07-14 | 2014-12-10 | ギリアード サイエンシーズ， インコーポレイテッド | Ｈｄａｃおよび／またはｃｄｋ阻害剤としてのイミダゾシルピリジン化合物 |
| EP2303841A1 (en) | 2008-07-14 | 2011-04-06 | Gilead Sciences, Inc. | Oxindolyl inhibitor compounds |
| KR20110038159A (ko) | 2008-07-28 | 2011-04-13 | 길리애드 사이언시즈, 인코포레이티드 | 사이클로알킬리덴 및 헤테로사이클로알킬리덴 히스톤 데아세틸라아제 억제제 화합물 |
| CA2763167A1 (en) | 2009-06-08 | 2010-12-16 | Gilead Sciences, Inc. | Cycloalkylcarbamate benzamide aniline hdac inhibitor compounds |
| AU2010259035A1 (en) | 2009-06-08 | 2011-12-08 | Gilead Sciences, Inc. | Alkanoylamino benzamide aniline HDAC inhibitor compounds |
-
2009
- 2009-07-14 CA CA2729965A patent/CA2729965A1/en not_active Abandoned
- 2009-07-14 NZ NZ590320A patent/NZ590320A/xx not_active IP Right Cessation
- 2009-07-14 US US12/502,967 patent/US8124764B2/en not_active Expired - Fee Related
- 2009-07-14 EP EP09790408A patent/EP2303881A2/en not_active Withdrawn
- 2009-07-14 AU AU2009271019A patent/AU2009271019A1/en not_active Abandoned
- 2009-07-14 JP JP2011518851A patent/JP5640006B2/ja not_active Expired - Fee Related
- 2009-07-14 WO PCT/US2009/050577 patent/WO2010009155A2/en not_active Ceased
- 2009-07-14 NZ NZ602832A patent/NZ602832A/en not_active IP Right Cessation
-
2014
- 2014-01-07 JP JP2014000750A patent/JP2014088420A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| NZ602832A (en) | 2014-04-30 |
| NZ590320A (en) | 2012-12-21 |
| WO2010009155A3 (en) | 2010-09-23 |
| JP2011528040A (ja) | 2011-11-10 |
| JP2014088420A (ja) | 2014-05-15 |
| EP2303881A2 (en) | 2011-04-06 |
| WO2010009155A2 (en) | 2010-01-21 |
| AU2009271019A1 (en) | 2010-01-21 |
| US8124764B2 (en) | 2012-02-28 |
| US20100029638A1 (en) | 2010-02-04 |
| JP5640006B2 (ja) | 2014-12-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20140714 |
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| FZDE | Discontinued |
Effective date: 20170314 |