HRP20110804T1 - Benzocikloheptapiridini kao inhibitori receptora tirozin kinaze met - Google Patents
Benzocikloheptapiridini kao inhibitori receptora tirozin kinaze met Download PDFInfo
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- HRP20110804T1 HRP20110804T1 HR20110804T HRP20110804T HRP20110804T1 HR P20110804 T1 HRP20110804 T1 HR P20110804T1 HR 20110804 T HR20110804 T HR 20110804T HR P20110804 T HRP20110804 T HR P20110804T HR P20110804 T1 HRP20110804 T1 HR P20110804T1
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- HR
- Croatia
- Prior art keywords
- cyclohepta
- benzo
- pyridin
- oxo
- methyl
- Prior art date
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- 102000027426 receptor tyrosine kinases Human genes 0.000 title abstract 2
- 108091008598 receptor tyrosine kinases Proteins 0.000 title abstract 2
- XYNHQVIVVBWVAG-UHFFFAOYSA-N 4h-cyclohepta[f]quinoline Chemical class C1=CC=CC=C2C3=CC=CNC3=CC=C21 XYNHQVIVVBWVAG-UHFFFAOYSA-N 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 18
- 206010028980 Neoplasm Diseases 0.000 claims abstract 6
- 201000011510 cancer Diseases 0.000 claims abstract 6
- 125000003118 aryl group Chemical group 0.000 claims 31
- 125000001424 substituent group Chemical group 0.000 claims 30
- 125000000217 alkyl group Chemical group 0.000 claims 28
- 125000000623 heterocyclic group Chemical group 0.000 claims 25
- -1 -O-aryl Chemical group 0.000 claims 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims 15
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 14
- 125000000304 alkynyl group Chemical group 0.000 claims 13
- 150000003839 salts Chemical class 0.000 claims 13
- 125000003342 alkenyl group Chemical group 0.000 claims 12
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 10
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 9
- 229910052760 oxygen Inorganic materials 0.000 claims 9
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 8
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 7
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 6
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims 6
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 125000002950 monocyclic group Chemical group 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims 5
- QVGIIXZAXKMWGF-UHFFFAOYSA-N 9-(2,2-difluoro-1-hydroxyethyl)-2-(1-methylpyrazol-4-yl)benzo[1,2]cyclohepta[2,4-b]pyridin-11-one Chemical compound C1=NN(C)C=C1C1=CN=C(C=CC=2C(=CC(=CC=2)C(O)C(F)F)C2=O)C2=C1 QVGIIXZAXKMWGF-UHFFFAOYSA-N 0.000 claims 4
- 125000006664 (C1-C3) perfluoroalkyl group Chemical group 0.000 claims 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 3
- 241000689227 Cora <basidiomycete fungus> Species 0.000 claims 3
- 125000005275 alkylenearyl group Chemical group 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- XNZVSOJRNKHDAQ-UHFFFAOYSA-N 4-[2-[[2-(1-methylpyrazol-4-yl)-11-oxobenzo[1,2]cyclohepta[2,4-b]pyridin-9-yl]amino]ethyl]morpholin-3-one Chemical compound C1=NN(C)C=C1C1=CN=C(C=CC=2C(=CC(NCCN3C(COCC3)=O)=CC=2)C2=O)C2=C1 XNZVSOJRNKHDAQ-UHFFFAOYSA-N 0.000 claims 2
- JTLQEKHDULWNCF-UHFFFAOYSA-N 9-(1,2-dihydroxyethyl)-2-(1-methylpyrazol-4-yl)benzo[1,2]cyclohepta[2,4-b]pyridin-11-one Chemical compound C1=NN(C)C=C1C1=CN=C(C=CC=2C(=CC(=CC=2)C(O)CO)C2=O)C2=C1 JTLQEKHDULWNCF-UHFFFAOYSA-N 0.000 claims 2
- QUVYHJOMTSLDBG-UHFFFAOYSA-N 9-(2-methoxyethylamino)-2-phenylbenzo[1,2]cyclohepta[2,4-b]pyridin-11-one Chemical compound C1=C2C(=O)C3=CC(NCCOC)=CC=C3C=CC2=NC=C1C1=CC=CC=C1 QUVYHJOMTSLDBG-UHFFFAOYSA-N 0.000 claims 2
- QVGIIXZAXKMWGF-GOSISDBHSA-N 9-[(1r)-2,2-difluoro-1-hydroxyethyl]-2-(1-methylpyrazol-4-yl)benzo[1,2]cyclohepta[2,4-b]pyridin-11-one Chemical compound C1=NN(C)C=C1C1=CN=C(C=CC=2C(=CC(=CC=2)[C@@H](O)C(F)F)C2=O)C2=C1 QVGIIXZAXKMWGF-GOSISDBHSA-N 0.000 claims 2
- AEPLHPQMFREUPA-UHFFFAOYSA-N 9-[(2,4-dimethoxyphenyl)methylamino]-2-(1h-pyrazol-5-yl)benzo[1,2]cyclohepta[2,4-b]pyridin-11-one Chemical compound COC1=CC(OC)=CC=C1CNC1=CC=C(C=CC=2C(=CC(=CN=2)C2=NNC=C2)C2=O)C2=C1 AEPLHPQMFREUPA-UHFFFAOYSA-N 0.000 claims 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- 206010006187 Breast cancer Diseases 0.000 claims 2
- 208000026310 Breast neoplasm Diseases 0.000 claims 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
- 206010009944 Colon cancer Diseases 0.000 claims 2
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 2
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- JOXWSDNHLSQKCC-UHFFFAOYSA-N ethenesulfonamide Chemical compound NS(=O)(=O)C=C JOXWSDNHLSQKCC-UHFFFAOYSA-N 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 206010017758 gastric cancer Diseases 0.000 claims 2
- 208000005017 glioblastoma Diseases 0.000 claims 2
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 2
- SZYARCOFJFUANJ-UHFFFAOYSA-N n-[11-oxo-2-(4-propan-2-ylpiperazin-1-yl)benzo[1,2]cyclohepta[2,4-b]pyridin-9-yl]methanesulfonamide Chemical compound C1CN(C(C)C)CCN1C1=CN=C(C=CC=2C(=CC(NS(C)(=O)=O)=CC=2)C2=O)C2=C1 SZYARCOFJFUANJ-UHFFFAOYSA-N 0.000 claims 2
- LZIMGNJOIGBJMI-UHFFFAOYSA-N n-[2-(1-methylpyrazol-4-yl)-11-oxobenzo[1,2]cyclohepta[2,4-b]pyridin-9-yl]azetidine-1-sulfonamide Chemical compound C1=NN(C)C=C1C1=CN=C(C=CC=2C(=CC(NS(=O)(=O)N3CCC3)=CC=2)C2=O)C2=C1 LZIMGNJOIGBJMI-UHFFFAOYSA-N 0.000 claims 2
- APRGMOVSNMXBGW-UHFFFAOYSA-N n-[2-[1-(3-hydroxypropyl)pyrazol-4-yl]-11-oxobenzo[1,2]cyclohepta[2,4-b]pyridin-9-yl]methanesulfonamide Chemical compound C1=C2C(=O)C3=CC(NS(=O)(=O)C)=CC=C3C=CC2=NC=C1C=1C=NN(CCCO)C=1 APRGMOVSNMXBGW-UHFFFAOYSA-N 0.000 claims 2
- 201000002528 pancreatic cancer Diseases 0.000 claims 2
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 201000011549 stomach cancer Diseases 0.000 claims 2
- ZAPRCSPGKMWNCA-UHFFFAOYSA-N (11-oxo-2-phenylbenzo[1,2]cyclohepta[2,4-b]pyridin-9-yl)methyl methanesulfinate Chemical compound C1=C2C(=O)C3=CC(COS(=O)C)=CC=C3C=CC2=NC=C1C1=CC=CC=C1 ZAPRCSPGKMWNCA-UHFFFAOYSA-N 0.000 claims 1
- PWEWKROHMINCBH-UHFFFAOYSA-N 1,1,1-trifluoro-n-[2-(1-methylpyrazol-4-yl)-11-oxobenzo[1,2]cyclohepta[2,4-b]pyridin-9-yl]methanesulfonamide Chemical compound C1=NN(C)C=C1C1=CN=C(C=CC=2C(=CC(NS(=O)(=O)C(F)(F)F)=CC=2)C2=O)C2=C1 PWEWKROHMINCBH-UHFFFAOYSA-N 0.000 claims 1
- DNHVFNDOHJKATM-UHFFFAOYSA-N 1-(2,2,2-trifluoroethyl)pyrazole Chemical compound FC(F)(F)CN1C=CC=N1 DNHVFNDOHJKATM-UHFFFAOYSA-N 0.000 claims 1
- NKKDJCNSASOKRX-UHFFFAOYSA-N 1-ethyl-3-(11-oxo-2-phenylbenzo[1,2]cyclohepta[2,4-b]pyridin-8-yl)urea Chemical compound C=1C(NC(=O)NCC)=CC=C(C(C2=C3)=O)C=1C=CC2=NC=C3C1=CC=CC=C1 NKKDJCNSASOKRX-UHFFFAOYSA-N 0.000 claims 1
- CRPHCQZUMGSVOP-UHFFFAOYSA-N 1-ethyl-3-[2-(1-methylpyrazol-4-yl)-11-oxobenzo[1,2]cyclohepta[2,4-b]pyridin-9-yl]urea Chemical compound C1=C2C(=O)C3=CC(NC(=O)NCC)=CC=C3C=CC2=NC=C1C=1C=NN(C)C=1 CRPHCQZUMGSVOP-UHFFFAOYSA-N 0.000 claims 1
- QGLVHCTZJWXHQT-UHFFFAOYSA-N 10-amino-2-phenylbenzo[3,4]cyclohepta[1,3-b]pyridin-11-one Chemical compound C1=C2C(=O)C=3C(N)=CC=CC=3C=CC2=NC=C1C1=CC=CC=C1 QGLVHCTZJWXHQT-UHFFFAOYSA-N 0.000 claims 1
- VVSDHWKWUPQCPD-UHFFFAOYSA-N 10-bromo-2-phenylbenzo[3,4]cyclohepta[1,3-b]pyridin-11-one Chemical compound C1=C2C(=O)C=3C(Br)=CC=CC=3C=CC2=NC=C1C1=CC=CC=C1 VVSDHWKWUPQCPD-UHFFFAOYSA-N 0.000 claims 1
- TWKWOJOTXVDFQI-UHFFFAOYSA-N 10-methoxy-2-phenylbenzo[3,4]cyclohepta[1,3-b]pyridin-11-one Chemical compound C1=C2C(=O)C=3C(OC)=CC=CC=3C=CC2=NC=C1C1=CC=CC=C1 TWKWOJOTXVDFQI-UHFFFAOYSA-N 0.000 claims 1
- JQSLCBGRDNQMAN-UHFFFAOYSA-N 10-methyl-2-phenylbenzo[1,2]cyclohepta[3,4-b]pyridin-11-one Chemical compound C1=C2C(=O)C=3C(C)=CC=CC=3C=CC2=NC=C1C1=CC=CC=C1 JQSLCBGRDNQMAN-UHFFFAOYSA-N 0.000 claims 1
- MLHXIJMZBZYSGG-UHFFFAOYSA-N 10-methylsulfanyl-2-phenylbenzo[3,4]cyclohepta[1,3-b]pyridin-11-one Chemical compound C1=C2C(=O)C=3C(SC)=CC=CC=3C=CC2=NC=C1C1=CC=CC=C1 MLHXIJMZBZYSGG-UHFFFAOYSA-N 0.000 claims 1
- GZVRMUXRVOZIHQ-UHFFFAOYSA-N 10-methylsulfonyl-2-phenylbenzo[3,4]cyclohepta[1,3-b]pyridin-11-one Chemical compound C1=C2C(=O)C=3C(S(=O)(=O)C)=CC=CC=3C=CC2=NC=C1C1=CC=CC=C1 GZVRMUXRVOZIHQ-UHFFFAOYSA-N 0.000 claims 1
- GLJLHTOONQGMPS-UHFFFAOYSA-N 11-oxo-2-phenylbenzo[1,2]cyclohepta[2,4-b]pyridine-9-carboxylic acid Chemical compound C1=C2C(=O)C3=CC(C(=O)O)=CC=C3C=CC2=NC=C1C1=CC=CC=C1 GLJLHTOONQGMPS-UHFFFAOYSA-N 0.000 claims 1
- HCLXLZGAYCTHQJ-UHFFFAOYSA-N 1h-cyclohepta[b]pyridine Chemical compound C1=CC=CC=C2NC=CC=C21 HCLXLZGAYCTHQJ-UHFFFAOYSA-N 0.000 claims 1
- QFIWRYPGJZRALK-UHFFFAOYSA-N 2,9-bis(1-methylpyrazol-4-yl)benzo[1,2]cyclohepta[2,4-b]pyridin-11-one Chemical compound C1=NN(C)C=C1C1=CC=C(C=CC=2C(=CC(=CN=2)C2=CN(C)N=C2)C2=O)C2=C1 QFIWRYPGJZRALK-UHFFFAOYSA-N 0.000 claims 1
- HDHUIRPEWMEKAF-UHFFFAOYSA-N 2,9-bis(pyridin-3-ylmethylamino)benzo[1,2]cyclohepta[2,4-b]pyridin-11-one Chemical compound C=1C=C2C=CC3=NC=C(NCC=4C=NC=CC=4)C=C3C(=O)C2=CC=1NCC1=CC=CN=C1 HDHUIRPEWMEKAF-UHFFFAOYSA-N 0.000 claims 1
- RYQDNMLGGZTCAH-UHFFFAOYSA-N 2,9-bis[(3-methylpyridin-4-yl)methylamino]benzo[1,2]cyclohepta[2,4-b]pyridin-11-one Chemical compound CC1=CN=CC=C1CNC1=CC=C(C=CC=2C(=CC(NCC=3C(=CN=CC=3)C)=CN=2)C2=O)C2=C1 RYQDNMLGGZTCAH-UHFFFAOYSA-N 0.000 claims 1
- CGJWNHQGQATCON-UHFFFAOYSA-N 2-(1-benzothiophen-3-yl)-9-[(2,4-dimethoxyphenyl)methylamino]benzo[1,2]cyclohepta[2,4-b]pyridin-11-one Chemical compound COC1=CC(OC)=CC=C1CNC1=CC=C(C=CC=2C(=CC(=CN=2)C=2C3=CC=CC=C3SC=2)C2=O)C2=C1 CGJWNHQGQATCON-UHFFFAOYSA-N 0.000 claims 1
- KKTIIYBITFAHGL-UHFFFAOYSA-N 2-(1-methylpyrazol-4-yl)-11-oxo-9-(sulfamoylamino)benzo[1,2]cyclohepta[2,4-b]pyridine Chemical compound C1=NN(C)C=C1C1=CN=C(C=CC=2C(=CC(NS(N)(=O)=O)=CC=2)C2=O)C2=C1 KKTIIYBITFAHGL-UHFFFAOYSA-N 0.000 claims 1
- MUROQGFUVQLMLP-UHFFFAOYSA-N 2-(1-methylpyrazol-4-yl)-11-oxo-9-[oxolan-3-ylmethyl(sulfamoyl)amino]benzo[1,2]cyclohepta[2,4-b]pyridine Chemical compound C1=NN(C)C=C1C1=CN=C(C=CC=2C(=CC(=CC=2)N(CC2COCC2)S(N)(=O)=O)C2=O)C2=C1 MUROQGFUVQLMLP-UHFFFAOYSA-N 0.000 claims 1
- MQDFQLQPZGZBME-UHFFFAOYSA-N 2-(1-methylpyrazol-4-yl)-9-(1h-pyrazol-5-yl)benzo[1,2]cyclohepta[2,4-b]pyridin-11-one Chemical compound C1=NN(C)C=C1C1=CN=C(C=CC=2C(=CC(=CC=2)C2=NNC=C2)C2=O)C2=C1 MQDFQLQPZGZBME-UHFFFAOYSA-N 0.000 claims 1
- WSIVBJWSBDRJOK-UHFFFAOYSA-N 2-(1-methylpyrazol-4-yl)-9-(1h-pyrrol-2-yl)benzo[1,2]cyclohepta[2,4-b]pyridin-11-one Chemical compound C1=NN(C)C=C1C1=CN=C(C=CC=2C(=CC(=CC=2)C=2NC=CC=2)C2=O)C2=C1 WSIVBJWSBDRJOK-UHFFFAOYSA-N 0.000 claims 1
- GSDGAGCIONKRFU-UHFFFAOYSA-N 2-(1-methylpyrazol-4-yl)-9-(2-phenylethylamino)benzo[1,2]cyclohepta[2,4-b]pyridin-11-one Chemical compound C1=NN(C)C=C1C1=CN=C(C=CC=2C(=CC(NCCC=3C=CC=CC=3)=CC=2)C2=O)C2=C1 GSDGAGCIONKRFU-UHFFFAOYSA-N 0.000 claims 1
- SBADQUVBPJZKAO-UHFFFAOYSA-N 2-(1-methylpyrazol-4-yl)-9-(oxan-4-ylmethylamino)benzo[1,2]cyclohepta[2,4-b]pyridin-11-one Chemical compound C1=NN(C)C=C1C1=CN=C(C=CC=2C(=CC(NCC3CCOCC3)=CC=2)C2=O)C2=C1 SBADQUVBPJZKAO-UHFFFAOYSA-N 0.000 claims 1
- KNFOGCSMKMSYCR-UHFFFAOYSA-N 2-(1-methylpyrazol-4-yl)-9-(oxolan-3-ylsulfamoylamino)benzo[1,2]cyclohepta[2,4-b]pyridin-11-one Chemical compound C1=NN(C)C=C1C1=CN=C(C=CC=2C(=CC(NS(=O)(=O)NC3COCC3)=CC=2)C2=O)C2=C1 KNFOGCSMKMSYCR-UHFFFAOYSA-N 0.000 claims 1
- FQOUSGGYWQWAEB-UHFFFAOYSA-N 2-(1-methylpyrazol-4-yl)-9-(propan-2-ylamino)benzo[1,2]cyclohepta[2,4-b]pyridin-11-one Chemical compound C1=C2C(=O)C3=CC(NC(C)C)=CC=C3C=CC2=NC=C1C=1C=NN(C)C=1 FQOUSGGYWQWAEB-UHFFFAOYSA-N 0.000 claims 1
- ILEKWOKNDGAHSV-UHFFFAOYSA-N 2-(1-methylpyrazol-4-yl)-9-(propylamino)benzo[1,2]cyclohepta[2,4-b]pyridin-11-one Chemical compound C1=C2C(=O)C3=CC(NCCC)=CC=C3C=CC2=NC=C1C=1C=NN(C)C=1 ILEKWOKNDGAHSV-UHFFFAOYSA-N 0.000 claims 1
- MUPFDLDAVLXKOI-UHFFFAOYSA-N 2-(1-methylpyrazol-4-yl)-9-[(1-methylpyrazol-4-yl)methyl-sulfamoylamino]-11-oxobenzo[1,2]cyclohepta[2,4-b]pyridine Chemical compound C1=NN(C)C=C1CN(S(N)(=O)=O)C1=CC=C(C=CC=2C(=CC(=CN=2)C2=CN(C)N=C2)C2=O)C2=C1 MUPFDLDAVLXKOI-UHFFFAOYSA-N 0.000 claims 1
- XKLYDKCXAYREQP-UHFFFAOYSA-N 2-(1-methylpyrazol-4-yl)-9-[(2-morpholin-4-yl-2-oxoethyl)amino]benzo[1,2]cyclohepta[2,4-b]pyridin-11-one Chemical compound C1=NN(C)C=C1C1=CN=C(C=CC=2C(=CC(NCC(=O)N3CCOCC3)=CC=2)C2=O)C2=C1 XKLYDKCXAYREQP-UHFFFAOYSA-N 0.000 claims 1
- YDNFEVRKANGEBD-UHFFFAOYSA-N 2-(1-methylpyrazol-4-yl)-9-[(2-phenylphenyl)methylamino]benzo[1,2]cyclohepta[2,4-b]pyridin-11-one Chemical compound C1=NN(C)C=C1C1=CN=C(C=CC=2C(=CC(NCC=3C(=CC=CC=3)C=3C=CC=CC=3)=CC=2)C2=O)C2=C1 YDNFEVRKANGEBD-UHFFFAOYSA-N 0.000 claims 1
- KUXTUKYXPCFRSP-UHFFFAOYSA-N 2-(1-methylpyrazol-4-yl)-9-[(3-methylpyridin-2-yl)methylamino]benzo[1,2]cyclohepta[2,4-b]pyridin-11-one Chemical compound CC1=CC=CN=C1CNC1=CC=C(C=CC=2C(=CC(=CN=2)C2=CN(C)N=C2)C2=O)C2=C1 KUXTUKYXPCFRSP-UHFFFAOYSA-N 0.000 claims 1
- PJTJSYVDINDALB-UHFFFAOYSA-N 2-(1-methylpyrazol-4-yl)-9-[(3-methylpyridin-4-yl)methylamino]benzo[1,2]cyclohepta[2,4-b]pyridin-11-one Chemical compound CC1=CN=CC=C1CNC1=CC=C(C=CC=2C(=CC(=CN=2)C2=CN(C)N=C2)C2=O)C2=C1 PJTJSYVDINDALB-UHFFFAOYSA-N 0.000 claims 1
- GMSPCYUKNKRLGT-UHFFFAOYSA-N 2-(1-methylpyrazol-4-yl)-9-[[2-(trifluoromethyl)phenyl]methylamino]benzo[1,2]cyclohepta[2,4-b]pyridin-11-one Chemical compound C1=NN(C)C=C1C1=CN=C(C=CC=2C(=CC(NCC=3C(=CC=CC=3)C(F)(F)F)=CC=2)C2=O)C2=C1 GMSPCYUKNKRLGT-UHFFFAOYSA-N 0.000 claims 1
- OWSLWZRHOAIWPU-UHFFFAOYSA-N 2-(1-methylpyrazol-4-yl)-9-[[2-(trifluoromethyl)phenyl]methylsulfamoylamino]benzo[1,2]cyclohepta[2,4-b]pyridin-11-one Chemical compound C1=NN(C)C=C1C1=CN=C(C=CC=2C(=CC(NS(=O)(=O)NCC=3C(=CC=CC=3)C(F)(F)F)=CC=2)C2=O)C2=C1 OWSLWZRHOAIWPU-UHFFFAOYSA-N 0.000 claims 1
- RMDYWRCSRBLNDI-UHFFFAOYSA-N 2-(1-methylpyrazol-4-yl)-9-[methyl(sulfamoyl)amino]-11-oxobenzo[1,2]cyclohepta[2,4-b]pyridine Chemical compound C1=C2C(=O)C3=CC(N(C)S(N)(=O)=O)=CC=C3C=CC2=NC=C1C=1C=NN(C)C=1 RMDYWRCSRBLNDI-UHFFFAOYSA-N 0.000 claims 1
- POYKPBNRJZJBHM-UHFFFAOYSA-N 2-(2-morpholin-4-ylethylamino)-n-(11-oxo-2-phenylbenzo[1,2]cyclohepta[2,4-b]pyridin-9-yl)ethanesulfonamide Chemical compound C=1C=C2C=CC3=NC=C(C=4C=CC=CC=4)C=C3C(=O)C2=CC=1NS(=O)(=O)CCNCCN1CCOCC1 POYKPBNRJZJBHM-UHFFFAOYSA-N 0.000 claims 1
- NVERIPULYVPZIC-UHFFFAOYSA-N 2-(4-acetylpiperazin-1-yl)-9-morpholin-4-ylbenzo[1,2]cyclohepta[2,4-b]pyridin-11-one Chemical compound C1CN(C(=O)C)CCN1C1=CN=C(C=CC=2C(=CC(=CC=2)N2CCOCC2)C2=O)C2=C1 NVERIPULYVPZIC-UHFFFAOYSA-N 0.000 claims 1
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- FSPPSDYIZICZIB-UHFFFAOYSA-N methyl 9-(dimethylsulfamoylamino)-11-oxobenzo[1,2]cyclohepta[2,4-b]pyridine-2-carboxylate Chemical compound C1=CC2=CC=C(NS(=O)(=O)N(C)C)C=C2C(=O)C2=CC(C(=O)OC)=CN=C21 FSPPSDYIZICZIB-UHFFFAOYSA-N 0.000 claims 1
- WXKUPXNRORPGDD-UHFFFAOYSA-N n-(11-hydroxy-2-phenyl-11h-benzo[1,2]cyclohepta[2,4-b]pyridin-9-yl)methanesulfonamide Chemical compound C1=C2C(O)C3=CC(NS(=O)(=O)C)=CC=C3C=CC2=NC=C1C1=CC=CC=C1 WXKUPXNRORPGDD-UHFFFAOYSA-N 0.000 claims 1
- GQYXXODNJWEUBY-UHFFFAOYSA-N n-(11-methoxy-2-phenyl-11h-benzo[1,2]cyclohepta[2,4-b]pyridin-9-yl)-n-methylmethanesulfonamide Chemical compound C1=C2C(OC)C3=CC(N(C)S(C)(=O)=O)=CC=C3C=CC2=NC=C1C1=CC=CC=C1 GQYXXODNJWEUBY-UHFFFAOYSA-N 0.000 claims 1
- CYQHDQDAICSDNP-UHFFFAOYSA-N n-(11-morpholin-4-yl-2-phenyl-11h-benzo[1,2]cyclohepta[2,4-b]pyridin-9-yl)methanesulfonamide Chemical compound C12=CC(NS(=O)(=O)C)=CC=C2C=CC2=NC=C(C=3C=CC=CC=3)C=C2C1N1CCOCC1 CYQHDQDAICSDNP-UHFFFAOYSA-N 0.000 claims 1
- AJNQYKAUTVNESQ-UHFFFAOYSA-N n-(11-oxo-2-phenyl-5,6-dihydrobenzo[1,2]cyclohepta[2,4-b]pyridin-9-yl)methanesulfonamide Chemical compound C1=C2C(=O)C3=CC(NS(=O)(=O)C)=CC=C3CCC2=NC=C1C1=CC=CC=C1 AJNQYKAUTVNESQ-UHFFFAOYSA-N 0.000 claims 1
- MYFKQNBVELDSBI-UHFFFAOYSA-N n-(11-oxo-2-phenylbenzo[1,2]cyclohepta[2,4-b]pyridin-9-yl)-2-phenylacetamide Chemical compound C=1C=C2C=CC3=NC=C(C=4C=CC=CC=4)C=C3C(=O)C2=CC=1NC(=O)CC1=CC=CC=C1 MYFKQNBVELDSBI-UHFFFAOYSA-N 0.000 claims 1
- VPPBQCXIBLEBOC-UHFFFAOYSA-N n-(11-oxo-2-phenylbenzo[1,2]cyclohepta[2,4-b]pyridin-9-yl)-2-pyrazol-1-ylethanesulfonamide Chemical compound C=1C=C2C=CC3=NC=C(C=4C=CC=CC=4)C=C3C(=O)C2=CC=1NS(=O)(=O)CCN1C=CC=N1 VPPBQCXIBLEBOC-UHFFFAOYSA-N 0.000 claims 1
- INJYIEXMRPUMGG-UHFFFAOYSA-N n-(11-oxo-2-phenylbenzo[1,2]cyclohepta[2,4-b]pyridin-9-yl)-2-pyrrolidin-1-ylethanesulfonamide Chemical compound C=1C=C2C=CC3=NC=C(C=4C=CC=CC=4)C=C3C(=O)C2=CC=1NS(=O)(=O)CCN1CCCC1 INJYIEXMRPUMGG-UHFFFAOYSA-N 0.000 claims 1
- HKVZAMSOCPLUIZ-UHFFFAOYSA-N n-(11-oxo-2-phenylbenzo[1,2]cyclohepta[2,4-b]pyridin-9-yl)acetamide Chemical compound C1=C2C(=O)C3=CC(NC(=O)C)=CC=C3C=CC2=NC=C1C1=CC=CC=C1 HKVZAMSOCPLUIZ-UHFFFAOYSA-N 0.000 claims 1
- QPITZSXYUYNGGX-UHFFFAOYSA-N n-(11-oxo-2-phenylbenzo[1,2]cyclohepta[2,4-b]pyridin-9-yl)benzenesulfonamide Chemical compound C=1C=C2C=CC3=NC=C(C=4C=CC=CC=4)C=C3C(=O)C2=CC=1NS(=O)(=O)C1=CC=CC=C1 QPITZSXYUYNGGX-UHFFFAOYSA-N 0.000 claims 1
- CCTSKVJIFBVZPK-UHFFFAOYSA-N n-(11-oxo-2-phenylbenzo[1,2]cyclohepta[2,4-b]pyridin-9-yl)ethanesulfonamide Chemical compound C1=C2C(=O)C3=CC(NS(=O)(=O)CC)=CC=C3C=CC2=NC=C1C1=CC=CC=C1 CCTSKVJIFBVZPK-UHFFFAOYSA-N 0.000 claims 1
- FUNHEVBLXUQXLG-UHFFFAOYSA-N n-(11-oxo-2-phenylbenzo[1,2]cyclohepta[2,4-b]pyridin-9-yl)methanesulfonamide Chemical compound C1=C2C(=O)C3=CC(NS(=O)(=O)C)=CC=C3C=CC2=NC=C1C1=CC=CC=C1 FUNHEVBLXUQXLG-UHFFFAOYSA-N 0.000 claims 1
- ZMKIPASBJUPDLI-UHFFFAOYSA-N n-(11-oxo-2-piperazin-2-ylbenzo[1,2]cyclohepta[2,4-b]pyridin-9-yl)methanesulfonamide Chemical compound C1=C2C(=O)C3=CC(NS(=O)(=O)C)=CC=C3C=CC2=NC=C1C1CNCCN1 ZMKIPASBJUPDLI-UHFFFAOYSA-N 0.000 claims 1
- BFGPCWYLULJFQP-UHFFFAOYSA-N n-(11-oxo-2-piperidin-1-ylbenzo[1,2]cyclohepta[2,4-b]pyridin-9-yl)methanesulfonamide Chemical compound C1=C2C(=O)C3=CC(NS(=O)(=O)C)=CC=C3C=CC2=NC=C1N1CCCCC1 BFGPCWYLULJFQP-UHFFFAOYSA-N 0.000 claims 1
- PXXBJZMFQIEIMN-UHFFFAOYSA-N n-(11-oxo-2-pyridin-3-ylbenzo[1,2]cyclohepta[2,4-b]pyridin-9-yl)methanesulfonamide Chemical compound C1=C2C(=O)C3=CC(NS(=O)(=O)C)=CC=C3C=CC2=NC=C1C1=CC=CN=C1 PXXBJZMFQIEIMN-UHFFFAOYSA-N 0.000 claims 1
- MZDWDIHAUKHDJF-UHFFFAOYSA-N n-(11-oxo-2-pyridin-4-ylbenzo[1,2]cyclohepta[2,4-b]pyridin-9-yl)methanesulfonamide Chemical compound C1=C2C(=O)C3=CC(NS(=O)(=O)C)=CC=C3C=CC2=NC=C1C1=CC=NC=C1 MZDWDIHAUKHDJF-UHFFFAOYSA-N 0.000 claims 1
- CYJYBSZEEQSVBG-UHFFFAOYSA-N n-(11-oxo-2-pyrimidin-5-ylbenzo[1,2]cyclohepta[2,4-b]pyridin-9-yl)methanesulfonamide Chemical compound C1=C2C(=O)C3=CC(NS(=O)(=O)C)=CC=C3C=CC2=NC=C1C1=CN=CN=C1 CYJYBSZEEQSVBG-UHFFFAOYSA-N 0.000 claims 1
- HZHHUZPQTUSSNZ-UHFFFAOYSA-N n-(11-oxo-2-pyrrolidin-1-ylbenzo[1,2]cyclohepta[2,4-b]pyridin-9-yl)methanesulfonamide Chemical compound C1=C2C(=O)C3=CC(NS(=O)(=O)C)=CC=C3C=CC2=NC=C1N1CCCC1 HZHHUZPQTUSSNZ-UHFFFAOYSA-N 0.000 claims 1
- REGDMYBNALRJTA-UHFFFAOYSA-N n-(11-oxo-2-quinolin-3-ylbenzo[1,2]cyclohepta[2,4-b]pyridin-9-yl)methanesulfonamide Chemical compound C1=CC2=NC=C(C=3C=C4C=CC=CC4=NC=3)C=C2C(=O)C2=CC(NS(=O)(=O)C)=CC=C21 REGDMYBNALRJTA-UHFFFAOYSA-N 0.000 claims 1
- QSHKYSQYVJAAFG-UHFFFAOYSA-N n-(11-oxo-2-quinolin-5-ylbenzo[1,2]cyclohepta[2,4-b]pyridin-9-yl)methanesulfonamide Chemical compound C1=CC2=NC=C(C=3C4=CC=CN=C4C=CC=3)C=C2C(=O)C2=CC(NS(=O)(=O)C)=CC=C21 QSHKYSQYVJAAFG-UHFFFAOYSA-N 0.000 claims 1
- TYLIRJVYMHMOTJ-UHFFFAOYSA-N n-(11-oxo-2-quinolin-6-ylbenzo[1,2]cyclohepta[2,4-b]pyridin-9-yl)methanesulfonamide Chemical compound C1=CC2=NC=C(C=3C=C4C=CC=NC4=CC=3)C=C2C(=O)C2=CC(NS(=O)(=O)C)=CC=C21 TYLIRJVYMHMOTJ-UHFFFAOYSA-N 0.000 claims 1
- NZCLQMZOAUHTDP-UHFFFAOYSA-N n-(11-oxo-2-quinolin-8-ylbenzo[1,2]cyclohepta[2,4-b]pyridin-9-yl)methanesulfonamide Chemical compound C1=CC2=NC=C(C=3C4=NC=CC=C4C=CC=3)C=C2C(=O)C2=CC(NS(=O)(=O)C)=CC=C21 NZCLQMZOAUHTDP-UHFFFAOYSA-N 0.000 claims 1
- SOMXERKTVVUGIZ-UHFFFAOYSA-N n-(11-oxo-2-thiophen-3-ylbenzo[1,2]cyclohepta[2,4-b]pyridin-9-yl)methanesulfonamide Chemical compound C1=C2C(=O)C3=CC(NS(=O)(=O)C)=CC=C3C=CC2=NC=C1C=1C=CSC=1 SOMXERKTVVUGIZ-UHFFFAOYSA-N 0.000 claims 1
- RQZDAXXFYXKUEH-UHFFFAOYSA-N n-(2-amino-11-oxobenzo[1,2]cyclohepta[2,4-b]pyridin-9-yl)methanesulfonamide Chemical compound C1=CC2=NC=C(N)C=C2C(=O)C2=CC(NS(=O)(=O)C)=CC=C21 RQZDAXXFYXKUEH-UHFFFAOYSA-N 0.000 claims 1
- FWUKVHAGVWYQML-UHFFFAOYSA-N n-(2-anilino-11-oxobenzo[1,2]cyclohepta[2,4-b]pyridin-9-yl)methanesulfonamide Chemical compound C1=C2C(=O)C3=CC(NS(=O)(=O)C)=CC=C3C=CC2=NC=C1NC1=CC=CC=C1 FWUKVHAGVWYQML-UHFFFAOYSA-N 0.000 claims 1
- GFKHVZNSYSAKRG-UHFFFAOYSA-N n-(2-chloro-11-hydroxy-11h-benzo[1,2]cyclohepta[2,4-b]pyridin-9-yl)methanesulfonamide Chemical compound C1=CC2=NC=C(Cl)C=C2C(O)C2=CC(NS(=O)(=O)C)=CC=C21 GFKHVZNSYSAKRG-UHFFFAOYSA-N 0.000 claims 1
- QNDODTDUMKWYBA-UHFFFAOYSA-N n-(2-chloro-11-oxobenzo[1,2]cyclohepta[2,4-b]pyridin-9-yl)-1,1,1-trifluoromethanesulfonamide Chemical compound C1=CC2=NC=C(Cl)C=C2C(=O)C2=CC(NS(=O)(=O)C(F)(F)F)=CC=C21 QNDODTDUMKWYBA-UHFFFAOYSA-N 0.000 claims 1
- PZOUKFKCORIFJE-UHFFFAOYSA-N n-(2-chloro-11-oxobenzo[1,2]cyclohepta[2,4-b]pyridin-9-yl)-2-imidazol-1-ylethanesulfonamide Chemical compound C1=C2C(=O)C3=CC(Cl)=CN=C3C=CC2=CC=C1NS(=O)(=O)CCN1C=CN=C1 PZOUKFKCORIFJE-UHFFFAOYSA-N 0.000 claims 1
- RCOSUSRIQHDOMJ-UHFFFAOYSA-N n-(2-chloro-11-oxobenzo[1,2]cyclohepta[2,4-b]pyridin-9-yl)-2-methoxyacetamide Chemical compound C1=CC2=NC=C(Cl)C=C2C(=O)C2=CC(NC(=O)COC)=CC=C21 RCOSUSRIQHDOMJ-UHFFFAOYSA-N 0.000 claims 1
- ZHKNBSXRNNIRGH-UHFFFAOYSA-N n-(2-chloro-11-oxobenzo[1,2]cyclohepta[2,4-b]pyridin-9-yl)methanesulfonamide Chemical compound C1=CC2=NC=C(Cl)C=C2C(=O)C2=CC(NS(=O)(=O)C)=CC=C21 ZHKNBSXRNNIRGH-UHFFFAOYSA-N 0.000 claims 1
- VSAYUQMHLGPRBG-UHFFFAOYSA-N n-(2-imidazo[1,2-a]pyrazin-3-yl-11-oxobenzo[1,2]cyclohepta[2,4-b]pyridin-9-yl)methanesulfonamide Chemical compound C1=CC2=NC=C(C=3N4C=CN=CC4=NC=3)C=C2C(=O)C2=CC(NS(=O)(=O)C)=CC=C21 VSAYUQMHLGPRBG-UHFFFAOYSA-N 0.000 claims 1
- DXQPMCCJZHDCHW-UHFFFAOYSA-N n-(2-methylpropyl)-4-[9-[(3-methylpyridin-2-yl)methylamino]-11-oxobenzo[1,2]cyclohepta[2,4-b]pyridin-2-yl]benzamide Chemical compound C1=CC(C(=O)NCC(C)C)=CC=C1C1=CN=C(C=CC=2C(=CC(NCC=3C(=CC=CN=3)C)=CC=2)C2=O)C2=C1 DXQPMCCJZHDCHW-UHFFFAOYSA-N 0.000 claims 1
- NENQLFCGPDUKQZ-UHFFFAOYSA-N n-(2-morpholin-4-yl-11-oxobenzo[1,2]cyclohepta[2,4-b]pyridin-9-yl)methanesulfonamide Chemical compound C1=C2C(=O)C3=CC(NS(=O)(=O)C)=CC=C3C=CC2=NC=C1N1CCOCC1 NENQLFCGPDUKQZ-UHFFFAOYSA-N 0.000 claims 1
- GOXPGXBOGJJZNG-UHFFFAOYSA-N n-(2-phenyl-11-piperidin-1-yl-11h-benzo[1,2]cyclohepta[2,4-b]pyridin-9-yl)methanesulfonamide Chemical compound C12=CC(NS(=O)(=O)C)=CC=C2C=CC2=NC=C(C=3C=CC=CC=3)C=C2C1N1CCCCC1 GOXPGXBOGJJZNG-UHFFFAOYSA-N 0.000 claims 1
- AAPKMLWLODKOBC-UHFFFAOYSA-N n-(2-phenyl-11-pyrrolidin-1-yl-11h-benzo[1,2]cyclohepta[2,4-b]pyridin-9-yl)methanesulfonamide Chemical compound C12=CC(NS(=O)(=O)C)=CC=C2C=CC2=NC=C(C=3C=CC=CC=3)C=C2C1N1CCCC1 AAPKMLWLODKOBC-UHFFFAOYSA-N 0.000 claims 1
- DXGRROZBCONKKL-UHFFFAOYSA-N n-(2-phenyl-11h-benzo[1,2]cyclohepta[2,4-b]pyridin-9-yl)methanesulfonamide Chemical compound C1=C2CC3=CC(NS(=O)(=O)C)=CC=C3C=CC2=NC=C1C1=CC=CC=C1 DXGRROZBCONKKL-UHFFFAOYSA-N 0.000 claims 1
- SJOWTWFTJLIOQW-UHFFFAOYSA-N n-[11-(azetidin-1-yl)-2-phenyl-11h-benzo[1,2]cyclohepta[2,4-b]pyridin-9-yl]methanesulfonamide Chemical compound C12=CC(NS(=O)(=O)C)=CC=C2C=CC2=NC=C(C=3C=CC=CC=3)C=C2C1N1CCC1 SJOWTWFTJLIOQW-UHFFFAOYSA-N 0.000 claims 1
- VZAKBKCQMRIWOE-UHFFFAOYSA-N n-[11-(benzylamino)-2-phenyl-11h-benzo[1,2]cyclohepta[2,4-b]pyridin-9-yl]methanesulfonamide Chemical compound C12=CC(NS(=O)(=O)C)=CC=C2C=CC2=NC=C(C=3C=CC=CC=3)C=C2C1NCC1=CC=CC=C1 VZAKBKCQMRIWOE-UHFFFAOYSA-N 0.000 claims 1
- XRBRVGQLXMYFCZ-UHFFFAOYSA-N n-[11-(cyclopropylamino)-2-phenyl-11h-benzo[1,2]cyclohepta[2,4-b]pyridin-9-yl]methanesulfonamide Chemical compound C12=CC(NS(=O)(=O)C)=CC=C2C=CC2=NC=C(C=3C=CC=CC=3)C=C2C1NC1CC1 XRBRVGQLXMYFCZ-UHFFFAOYSA-N 0.000 claims 1
- MOMPOOJDNPAHDG-UHFFFAOYSA-N n-[11-(dimethylamino)-2-phenyl-11h-benzo[1,2]cyclohepta[2,4-b]pyridin-9-yl]methanesulfonamide Chemical compound C1=C2C(N(C)C)C3=CC(NS(C)(=O)=O)=CC=C3C=CC2=NC=C1C1=CC=CC=C1 MOMPOOJDNPAHDG-UHFFFAOYSA-N 0.000 claims 1
- UQIJJFSVVIRSQZ-UHFFFAOYSA-N n-[11-hydroxy-2-[3-(trifluoromethyl)-6,8-dihydro-5h-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-11h-benzo[1,2]cyclohepta[2,4-b]pyridin-9-yl]methanesulfonamide Chemical compound C1=CC2=NC=C(N3CC=4N(C(=NN=4)C(F)(F)F)CC3)C=C2C(O)C2=CC(NS(=O)(=O)C)=CC=C21 UQIJJFSVVIRSQZ-UHFFFAOYSA-N 0.000 claims 1
- VRPWUMAWKRKDCH-UHFFFAOYSA-N n-[11-oxo-2-(1,2-thiazol-4-yl)benzo[1,2]cyclohepta[2,4-b]pyridin-9-yl]methanesulfonamide Chemical compound C1=C2C(=O)C3=CC(NS(=O)(=O)C)=CC=C3C=CC2=NC=C1C=1C=NSC=1 VRPWUMAWKRKDCH-UHFFFAOYSA-N 0.000 claims 1
- FLOLTPKQTWLRNJ-UHFFFAOYSA-N n-[11-oxo-2-(1,2-thiazol-5-yl)benzo[1,2]cyclohepta[2,4-b]pyridin-9-yl]methanesulfonamide Chemical compound C1=C2C(=O)C3=CC(NS(=O)(=O)C)=CC=C3C=CC2=NC=C1C1=CC=NS1 FLOLTPKQTWLRNJ-UHFFFAOYSA-N 0.000 claims 1
- CCDVIMAOMWBTBA-UHFFFAOYSA-N n-[11-oxo-2-(1,3-thiazol-4-yl)benzo[1,2]cyclohepta[2,4-b]pyridin-9-yl]methanesulfonamide Chemical compound C1=C2C(=O)C3=CC(NS(=O)(=O)C)=CC=C3C=CC2=NC=C1C1=CSC=N1 CCDVIMAOMWBTBA-UHFFFAOYSA-N 0.000 claims 1
- YXZQJAAWTFRHLL-UHFFFAOYSA-N n-[11-oxo-2-(1-phenylethylamino)benzo[1,2]cyclohepta[2,4-b]pyridin-9-yl]methanesulfonamide Chemical compound C=1N=C2C=CC3=CC=C(NS(C)(=O)=O)C=C3C(=O)C2=CC=1NC(C)C1=CC=CC=C1 YXZQJAAWTFRHLL-UHFFFAOYSA-N 0.000 claims 1
- STZCMWVPVNAOCM-UHFFFAOYSA-N n-[11-oxo-2-(1-propan-2-ylpyrazol-4-yl)benzo[1,2]cyclohepta[2,4-b]pyridin-9-yl]methanesulfonamide Chemical compound C1=NN(C(C)C)C=C1C1=CN=C(C=CC=2C(=CC(NS(C)(=O)=O)=CC=2)C2=O)C2=C1 STZCMWVPVNAOCM-UHFFFAOYSA-N 0.000 claims 1
- AVMWSSKWUTUOIM-UHFFFAOYSA-N n-[11-oxo-2-(1-propylpyrazol-4-yl)benzo[1,2]cyclohepta[2,4-b]pyridin-9-yl]methanesulfonamide Chemical compound C1=NN(CCC)C=C1C1=CN=C(C=CC=2C(=CC(NS(C)(=O)=O)=CC=2)C2=O)C2=C1 AVMWSSKWUTUOIM-UHFFFAOYSA-N 0.000 claims 1
- HIWCCVNCPXCPMR-UHFFFAOYSA-N n-[11-oxo-2-(1h-pyrazol-4-yl)benzo[1,2]cyclohepta[2,4-b]pyridin-9-yl]methanesulfonamide Chemical compound C1=C2C(=O)C3=CC(NS(=O)(=O)C)=CC=C3C=CC2=NC=C1C=1C=NNC=1 HIWCCVNCPXCPMR-UHFFFAOYSA-N 0.000 claims 1
- MKPURBBSKFEJAT-UHFFFAOYSA-N n-[11-oxo-2-(1h-pyrazol-5-yl)benzo[1,2]cyclohepta[2,4-b]pyridin-9-yl]methanesulfonamide Chemical compound C1=C2C(=O)C3=CC(NS(=O)(=O)C)=CC=C3C=CC2=NC=C1C=1C=CNN=1 MKPURBBSKFEJAT-UHFFFAOYSA-N 0.000 claims 1
- ONJZQISPOVLZPG-UHFFFAOYSA-N n-[11-oxo-2-(4-pyridin-3-ylpiperazin-1-yl)benzo[1,2]cyclohepta[2,4-b]pyridin-9-yl]methanesulfonamide Chemical compound C1=C2C(=O)C3=CC(NS(=O)(=O)C)=CC=C3C=CC2=NC=C1N(CC1)CCN1C1=CC=CN=C1 ONJZQISPOVLZPG-UHFFFAOYSA-N 0.000 claims 1
- LDXAWHYVTUZCLK-UHFFFAOYSA-N n-[11-oxo-2-(4-quinolin-2-ylpiperazin-1-yl)benzo[1,2]cyclohepta[2,4-b]pyridin-9-yl]methanesulfonamide Chemical compound C1=CC2=NC=C(N3CCN(CC3)C=3N=C4C=CC=CC4=CC=3)C=C2C(=O)C2=CC(NS(=O)(=O)C)=CC=C21 LDXAWHYVTUZCLK-UHFFFAOYSA-N 0.000 claims 1
- WFRLGJPBGZGFFI-UHFFFAOYSA-N n-[11-oxo-2-(pyridin-2-ylamino)benzo[1,2]cyclohepta[2,4-b]pyridin-9-yl]methanesulfonamide Chemical compound C1=C2C(=O)C3=CC(NS(=O)(=O)C)=CC=C3C=CC2=NC=C1NC1=CC=CC=N1 WFRLGJPBGZGFFI-UHFFFAOYSA-N 0.000 claims 1
- LLCWEODGRDAQHZ-UHFFFAOYSA-N n-[11-oxo-2-(pyridin-4-ylamino)benzo[1,2]cyclohepta[2,4-b]pyridin-9-yl]methanesulfonamide Chemical compound C1=C2C(=O)C3=CC(NS(=O)(=O)C)=CC=C3C=CC2=NC=C1NC1=CC=NC=C1 LLCWEODGRDAQHZ-UHFFFAOYSA-N 0.000 claims 1
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- NLLPVLPVPFUHIL-UHFFFAOYSA-N tert-butyl 4-[4-[9-[(3-methylpyridin-2-yl)methylamino]-11-oxobenzo[1,2]cyclohepta[2,4-b]pyridin-2-yl]phenyl]piperazine-1-carboxylate Chemical compound CC1=CC=CN=C1CNC1=CC=C(C=CC=2C(=CC(=CN=2)C=2C=CC(=CC=2)N2CCN(CC2)C(=O)OC(C)(C)C)C2=O)C2=C1 NLLPVLPVPFUHIL-UHFFFAOYSA-N 0.000 claims 1
- XRLXOKDTBQYXRY-UHFFFAOYSA-N tert-butyl 4-[9-(methanesulfonamido)-11-oxobenzo[1,2]cyclohepta[2,4-b]pyridin-2-yl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1=CN=C(C=CC=2C(=CC(NS(C)(=O)=O)=CC=2)C2=O)C2=C1 XRLXOKDTBQYXRY-UHFFFAOYSA-N 0.000 claims 1
- XSYVHZKYCJRQBQ-UHFFFAOYSA-N tert-butyl n-[[2-(1-methylpyrazol-4-yl)-11-oxobenzo[1,2]cyclohepta[2,4-b]pyridin-9-yl]sulfamoyl]carbamate Chemical compound C1=NN(C)C=C1C1=CN=C(C=CC=2C(=CC(NS(=O)(=O)NC(=O)OC(C)(C)C)=CC=2)C2=O)C2=C1 XSYVHZKYCJRQBQ-UHFFFAOYSA-N 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 2
- OZVMEJXYSDZMDV-UHFFFAOYSA-N 11h-benzo[1,2]cyclohepta[3,4-b]pyridine Chemical class C1=CC2=NC=CC=C2CC2=CC=CC=C21 OZVMEJXYSDZMDV-UHFFFAOYSA-N 0.000 abstract 1
- 241000124008 Mammalia Species 0.000 abstract 1
- 230000001413 cellular effect Effects 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000002062 proliferating effect Effects 0.000 abstract 1
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ATE524445T1 (de) | 2005-06-23 | 2011-09-15 | Merck Sharp & Dohme | Benzocycloheptapyridine als inhibitoren der tyrosinkinase met |
WO2007050380A2 (en) | 2005-10-21 | 2007-05-03 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
TW200813021A (en) * | 2006-07-10 | 2008-03-16 | Merck & Co Inc | Tyrosine kinase inhibitors |
US8642067B2 (en) | 2007-04-02 | 2014-02-04 | Allergen, Inc. | Methods and compositions for intraocular administration to treat ocular conditions |
WO2009023846A2 (en) * | 2007-08-15 | 2009-02-19 | The Research Foundation Of State University Of New York | Methods for heat shock protein dependent cancer treatment |
US7893081B2 (en) | 2007-12-20 | 2011-02-22 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
WO2011039527A1 (en) | 2009-09-30 | 2011-04-07 | Merck Sharp & Dohme Ltd | Formulations for c-met kinase inhibitors |
AU2010300930B2 (en) | 2009-09-30 | 2014-09-11 | Merck Sharp & Dohme (Uk) Limited | Crystalline hydrochloride salts of c-MET kinase inhibitors |
US20110130374A1 (en) * | 2009-11-30 | 2011-06-02 | Biosearch(2007) Ltd. | Small Pyrimidine Derivatives and Methods of Use Thereof |
CN101857594B (zh) * | 2010-06-18 | 2013-04-03 | 南方医科大学 | 一种四氢吡啶并吲哚类化合物及其制备方法和应用 |
WO2012003338A1 (en) | 2010-07-01 | 2012-01-05 | Takeda Pharmaceutical Company Limited | COMBINATION OF A cMET INHIBITOR AND AN ANTIBODY TO HGF AND/OR cMET |
JP5792128B2 (ja) | 2011-07-29 | 2015-10-07 | 富士フイルム株式会社 | 1,5−ナフチリジン誘導体又はその塩 |
JP6187942B2 (ja) | 2012-03-02 | 2017-08-30 | ザ ボード オブ トラスティーズ オブ ザ ユニヴァーシティー オブ イリノイ | 二重複合活性化による強力な抗癌活性 |
JP6222608B2 (ja) | 2012-03-06 | 2017-11-01 | ザ ボード オブ トラスティーズ オブ ザ ユニヴァーシティー オブ イリノイ | 膠芽腫のためのプロカスパーゼ併用療法 |
BR112014022103B1 (pt) | 2012-03-06 | 2022-04-19 | The Board Of Trustees Of The University Of Illinois | Composições e seus usos |
WO2014004376A2 (en) | 2012-06-26 | 2014-01-03 | Del Mar Pharmaceuticals | Methods for treating tyrosine-kinase-inhibitor-resistant malignancies in patients with genetic polymorphisms or ahi1 dysregulations or mutations employing dianhydrogalactitol, diacetyldianhydrogalactitol, dibromodulcitol, or analogs or derivatives thereof |
WO2014150996A1 (en) * | 2013-03-15 | 2014-09-25 | Cba Pharma, Inc. | Cancer treatment |
KR20160061911A (ko) | 2013-04-08 | 2016-06-01 | 데니스 엠. 브라운 | 최적하 투여된 화학 화합물의 치료 효과 |
EP3229836B1 (en) | 2014-12-09 | 2019-11-13 | Institut National de la Sante et de la Recherche Medicale (INSERM) | Human monoclonal antibodies against axl |
WO2016094361A1 (en) * | 2014-12-10 | 2016-06-16 | Southern Research Institute | Antiviral agents |
WO2016135041A1 (en) | 2015-02-26 | 2016-09-01 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Fusion proteins and antibodies comprising thereof for promoting apoptosis |
WO2017161004A1 (en) * | 2016-03-15 | 2017-09-21 | University Of South Florida | PKCδ INHIBITOR FORMULATIONS AND USES THEREOF CROSS-REFERENCE TO RELATED APPLICATIONS |
WO2019099873A1 (en) | 2017-11-17 | 2019-05-23 | The Board Of Trustees Of The University Of Illinois | Cancer therapy by degrading dual mek signaling |
EA202192575A1 (ru) | 2019-03-21 | 2022-01-14 | Онксео | Соединения dbait в сочетании с ингибиторами киназ для лечения рака |
US20220401436A1 (en) | 2019-11-08 | 2022-12-22 | INSERM (Institute National de la Santé et de la Recherche Médicale) | Methods for the treatment of cancers that have acquired resistance to kinase inhibitors |
WO2021148581A1 (en) | 2020-01-22 | 2021-07-29 | Onxeo | Novel dbait molecule and its use |
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2006
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- 2006-06-22 US US11/921,350 patent/US8207186B2/en active Active
- 2006-06-22 EP EP06785313A patent/EP1896421B1/en active Active
- 2006-06-22 WO PCT/US2006/024247 patent/WO2007002254A2/en active Application Filing
- 2006-06-22 JP JP2008506834A patent/JP4119478B1/ja active Active
- 2006-06-22 RU RU2008102381/04A patent/RU2408584C2/ru not_active IP Right Cessation
- 2006-06-22 US US11/473,273 patent/US7550478B2/en active Active
- 2006-06-22 AU AU2006262172A patent/AU2006262172B2/en active Active
- 2006-06-22 CA CA2611530A patent/CA2611530C/en active Active
- 2006-06-22 SI SI200631207T patent/SI1896421T1/sl unknown
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WO2007002254A3 (en) | 2007-05-18 |
JP2008156336A (ja) | 2008-07-10 |
CA2611530A1 (en) | 2007-01-04 |
RU2408584C2 (ru) | 2011-01-10 |
DK1896421T3 (da) | 2012-01-09 |
AU2006262172A1 (en) | 2007-01-04 |
ATE524445T1 (de) | 2011-09-15 |
JP2008536877A (ja) | 2008-09-11 |
EP1896421A2 (en) | 2008-03-12 |
US7550478B2 (en) | 2009-06-23 |
JP5086762B2 (ja) | 2012-11-28 |
EP1896421B1 (en) | 2011-09-14 |
AU2006262172B2 (en) | 2010-05-27 |
JP4119478B1 (ja) | 2008-07-16 |
US20090197908A1 (en) | 2009-08-06 |
US20060293358A1 (en) | 2006-12-28 |
US8207186B2 (en) | 2012-06-26 |
CA2611530C (en) | 2012-11-20 |
WO2007002254A2 (en) | 2007-01-04 |
SI1896421T1 (sl) | 2012-01-31 |
RU2008102381A (ru) | 2009-07-27 |
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