JP2004534010A5 - - Google Patents
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- Publication number
- JP2004534010A5 JP2004534010A5 JP2002577817A JP2002577817A JP2004534010A5 JP 2004534010 A5 JP2004534010 A5 JP 2004534010A5 JP 2002577817 A JP2002577817 A JP 2002577817A JP 2002577817 A JP2002577817 A JP 2002577817A JP 2004534010 A5 JP2004534010 A5 JP 2004534010A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- hydroxy
- ethylamino
- pyridin
- benzimidazol
- 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.)
- Withdrawn
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- 229910052739 hydrogen Inorganic materials 0.000 claims 77
- 239000001257 hydrogen Substances 0.000 claims 71
- -1 sulfoxy, sulfonyl Chemical group 0.000 claims 71
- 150000001875 compounds Chemical class 0.000 claims 51
- 150000002431 hydrogen Chemical class 0.000 claims 51
- 125000000217 alkyl group Chemical group 0.000 claims 46
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 31
- 125000003545 alkoxy group Chemical group 0.000 claims 23
- 125000001072 heteroaryl group Chemical group 0.000 claims 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 20
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 20
- 125000001475 halogen functional group Chemical group 0.000 claims 17
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 17
- 125000003118 aryl group Chemical group 0.000 claims 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 16
- 125000003342 alkenyl group Chemical group 0.000 claims 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims 15
- 125000005309 thioalkoxy group Chemical group 0.000 claims 15
- 150000003573 thiols Chemical class 0.000 claims 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 13
- 229910052731 fluorine Inorganic materials 0.000 claims 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 12
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 8
- 229910052794 bromium Inorganic materials 0.000 claims 8
- 229910052736 halogen Inorganic materials 0.000 claims 8
- 150000002367 halogens Chemical class 0.000 claims 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 7
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 7
- 229910052801 chlorine Inorganic materials 0.000 claims 7
- 239000000460 chlorine Substances 0.000 claims 7
- 239000011737 fluorine Substances 0.000 claims 7
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- 125000000547 substituted alkyl group Chemical group 0.000 claims 5
- ZNGWEEUXTBNKFR-UHFFFAOYSA-N 1,4-oxazepane Chemical compound C1CNCCOC1 ZNGWEEUXTBNKFR-UHFFFAOYSA-N 0.000 claims 4
- 241000124008 Mammalia Species 0.000 claims 4
- 125000003282 alkyl amino group Chemical group 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims 4
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 3
- OTOIUCLFSQHFOX-UHFFFAOYSA-N 3-sulfonylmorpholine Chemical compound O=S(=O)=C1COCCN1 OTOIUCLFSQHFOX-UHFFFAOYSA-N 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims 2
- WOXFMYVTSLAQMO-UHFFFAOYSA-N 2-Pyridinemethanamine Chemical compound NCC1=CC=CC=N1 WOXFMYVTSLAQMO-UHFFFAOYSA-N 0.000 claims 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 2
- SLYJOQJAIBXMFF-FQEVSTJZSA-N 4-[[(2S)-1-hydroxy-3-phenylpropan-2-yl]amino]-3-(4-methyl-6-piperidin-1-yl-1H-benzimidazol-2-yl)-1H-pyridin-2-one Chemical compound C([C@@H](CO)NC1=C(C(NC=C1)=O)C=1NC=2C=C(C=C(C=2N=1)C)N1CCCCC1)C1=CC=CC=C1 SLYJOQJAIBXMFF-FQEVSTJZSA-N 0.000 claims 2
- GGNQGVSKUWHOKX-UHFFFAOYSA-N 4-[[2-(3-bromophenyl)-2-hydroxyethyl]amino]-3-(4-methyl-6-piperazin-1-yl-1H-benzimidazol-2-yl)-1H-pyridin-2-one Chemical compound N=1C=2C(C)=CC(N3CCNCC3)=CC=2NC=1C(C(NC=C1)=O)=C1NCC(O)C1=CC=CC(Br)=C1 GGNQGVSKUWHOKX-UHFFFAOYSA-N 0.000 claims 2
- UIUYQDFIVJOTTH-UHFFFAOYSA-N 4-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]-3-(4-methyl-6-piperazin-1-yl-1H-benzimidazol-2-yl)-1H-pyridin-2-one Chemical compound N=1C=2C(C)=CC(N3CCNCC3)=CC=2NC=1C(C(NC=C1)=O)=C1NCC(O)C1=CC=CC(Cl)=C1 UIUYQDFIVJOTTH-UHFFFAOYSA-N 0.000 claims 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims 2
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims 2
- 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 2
- 108010053099 Vascular Endothelial Growth Factor Receptor-2 Proteins 0.000 claims 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Natural products CC1OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)NC4C(=O)NC(C(N5CCCC5C(=O)N(C)CC(=O)N(C)C(C(C)C)C(=O)OC4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-UHFFFAOYSA-N 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 2
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 2
- XPTAUSRPHWOZPN-UHFFFAOYSA-N morpholin-4-yl hydrogen sulfate Chemical compound OS(=O)(=O)ON1CCOCC1 XPTAUSRPHWOZPN-UHFFFAOYSA-N 0.000 claims 2
- 229940127084 other anti-cancer agent Drugs 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 2
- WDELNBOQCPAGPI-KRWDZBQOSA-N (2s)-2-[[6-chloro-5-(6-imidazol-1-yl-4-methyl-1h-benzimidazol-2-yl)pyrimidin-4-yl]amino]-3-phenylpropan-1-ol Chemical compound C([C@@H](CO)NC1=NC=NC(Cl)=C1C=1NC=2C=C(C=C(C=2N=1)C)N1C=NC=C1)C1=CC=CC=C1 WDELNBOQCPAGPI-KRWDZBQOSA-N 0.000 claims 1
- VEEGZPWAAPPXRB-BJMVGYQFSA-N (3e)-3-(1h-imidazol-5-ylmethylidene)-1h-indol-2-one Chemical compound O=C1NC2=CC=CC=C2\C1=C/C1=CN=CN1 VEEGZPWAAPPXRB-BJMVGYQFSA-N 0.000 claims 1
- LKJPYSCBVHEWIU-KRWDZBQOSA-N (R)-bicalutamide Chemical compound C([C@@](O)(C)C(=O)NC=1C=C(C(C#N)=CC=1)C(F)(F)F)S(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-KRWDZBQOSA-N 0.000 claims 1
- OTPDWCMLUKMQNO-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrimidine Chemical compound C1NCC=CN1 OTPDWCMLUKMQNO-UHFFFAOYSA-N 0.000 claims 1
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical group C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 claims 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical group C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims 1
- HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 claims 1
- IFNWESYYDINUHV-UHFFFAOYSA-N 2,6-dimethylpiperazine Chemical compound CC1CNCC(C)N1 IFNWESYYDINUHV-UHFFFAOYSA-N 0.000 claims 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims 1
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- JOMNTHCQHJPVAZ-UHFFFAOYSA-N 2-methylpiperazine Chemical compound CC1CNCCN1 JOMNTHCQHJPVAZ-UHFFFAOYSA-N 0.000 claims 1
- COZVWKMJBNLADG-HNNXBMFYSA-N 3-(1H-benzimidazol-2-yl)-4-[[(2S)-1-hydroxy-3-phenylpropan-2-yl]amino]-1H-pyridin-2-one Chemical compound C([C@@H](CO)NC1=C(C(=O)NC=C1)C=1NC2=CC=CC=C2N=1)C1=CC=CC=C1 COZVWKMJBNLADG-HNNXBMFYSA-N 0.000 claims 1
- XVTGMPIWLFRYCU-UHFFFAOYSA-N 3-(1H-benzimidazol-2-yl)-4-[[2-(3-bromo-4-methoxyphenyl)-2-hydroxyethyl]amino]-1H-pyridin-2-one Chemical compound C1=C(Br)C(OC)=CC=C1C(O)CNC1=C(C=2NC3=CC=CC=C3N=2)C(=O)NC=C1 XVTGMPIWLFRYCU-UHFFFAOYSA-N 0.000 claims 1
- CMYZQDNEXKMVAP-UHFFFAOYSA-N 3-(1H-benzimidazol-2-yl)-4-[[2-(3-bromophenyl)-2-hydroxyethyl]amino]-1H-pyridin-2-one Chemical compound C1=CNC(=O)C(C=2NC3=CC=CC=C3N=2)=C1NCC(O)C1=CC=CC(Br)=C1 CMYZQDNEXKMVAP-UHFFFAOYSA-N 0.000 claims 1
- OBHSRNCZUIOTPY-OAQYLSRUSA-N 3-[4-bromo-6-(morpholin-4-ylmethyl)-1H-benzimidazol-2-yl]-4-[[(2S)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]-1H-pyridin-2-one Chemical compound C([C@@H](O)C=1C=C(Cl)C=CC=1)NC=1C=CNC(=O)C=1C(NC1=C2)=NC1=C(Br)C=C2CN1CCOCC1 OBHSRNCZUIOTPY-OAQYLSRUSA-N 0.000 claims 1
- TUZKEXPUYPJNDF-UHFFFAOYSA-N 3-[6-(4-acetylpiperazin-1-yl)-4-methyl-1H-benzimidazol-2-yl]-4-[[2-(3-bromophenyl)-2-hydroxyethyl]amino]-1H-pyridin-2-one Chemical compound C1CN(C(=O)C)CCN1C1=CC(C)=C(N=C(N2)C=3C(NC=CC=3NCC(O)C=3C=C(Br)C=CC=3)=O)C2=C1 TUZKEXPUYPJNDF-UHFFFAOYSA-N 0.000 claims 1
- DGQFUGZAZIEOTL-SANMLTNESA-N 3-[6-(4-benzylpiperazin-1-yl)-4-methyl-1H-benzimidazol-2-yl]-4-[[(2S)-1-hydroxy-3-phenylpropan-2-yl]amino]-1H-pyridin-2-one Chemical compound C([C@@H](CO)NC1=C(C(NC=C1)=O)C=1NC=2C=C(C=C(C=2N=1)C)N1CCN(CC=2C=CC=CC=2)CC1)C1=CC=CC=C1 DGQFUGZAZIEOTL-SANMLTNESA-N 0.000 claims 1
- QLARNLBZNLHNOT-UHFFFAOYSA-N 3-[6-(aminomethyl)-4-methyl-1H-benzimidazol-2-yl]-4-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]-1H-pyridin-2-one Chemical compound N=1C=2C(C)=CC(CN)=CC=2NC=1C(C(NC=C1)=O)=C1NCC(O)C1=CC=CC(Cl)=C1 QLARNLBZNLHNOT-UHFFFAOYSA-N 0.000 claims 1
- HGDHHEZBLVABGA-UHFFFAOYSA-N 3-[6-[4-(2-chloroacetyl)piperazin-1-yl]-4-methyl-1H-benzimidazol-2-yl]-4-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]-1H-pyridin-2-one Chemical compound N=1C=2C(C)=CC(N3CCN(CC3)C(=O)CCl)=CC=2NC=1C(C(NC=C1)=O)=C1NCC(O)C1=CC=CC(Cl)=C1 HGDHHEZBLVABGA-UHFFFAOYSA-N 0.000 claims 1
- GISVYEBHXVVYFQ-NRFANRHFSA-N 3-[6-[4-(2-hydroxyethyl)piperazin-1-yl]-4-methyl-1H-benzimidazol-2-yl]-4-[[(2S)-1-hydroxy-3-phenylpropan-2-yl]amino]-1H-pyridin-2-one Chemical compound C([C@@H](CO)NC1=C(C(NC=C1)=O)C=1NC=2C=C(C=C(C=2N=1)C)N1CCN(CCO)CC1)C1=CC=CC=C1 GISVYEBHXVVYFQ-NRFANRHFSA-N 0.000 claims 1
- AOJJSUZBOXZQNB-VTZDEGQISA-N 4'-epidoxorubicin 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-VTZDEGQISA-N 0.000 claims 1
- AMJILRTVLRYXLQ-HXUWFJFHSA-N 4-[[(1S)-2-hydroxy-1-phenylethyl]amino]-3-(6-imidazol-1-yl-4-methyl-1H-benzimidazol-2-yl)-1H-pyridin-2-one Chemical compound C1([C@@H](CO)NC2=C(C(NC=C2)=O)C=2NC=3C=C(C=C(C=3N=2)C)N2C=NC=C2)=CC=CC=C1 AMJILRTVLRYXLQ-HXUWFJFHSA-N 0.000 claims 1
- QCDSKOUKWJFTKU-OFNKIYASSA-N 4-[[(1S,2R)-1-hydroxy-2,3-dihydro-1H-inden-2-yl]amino]-3-(6-imidazol-1-yl-4-methyl-1H-benzimidazol-2-yl)-1H-pyridin-2-one Chemical compound Cc1cc(cc2[nH]c(nc12)-c1c(N[C@@H]2Cc3ccccc3[C@@H]2O)cc[nH]c1=O)-n1ccnc1 QCDSKOUKWJFTKU-OFNKIYASSA-N 0.000 claims 1
- LQRBWXDBMNHGCK-FQEVSTJZSA-N 4-[[(2R)-2-hydroxy-2-phenylethyl]amino]-3-(6-imidazol-1-yl-4-methyl-1H-benzimidazol-2-yl)-1H-pyridin-2-one Chemical compound C1([C@@H](O)CNC2=C(C(NC=C2)=O)C=2NC=3C=C(C=C(C=3N=2)C)N2C=NC=C2)=CC=CC=C1 LQRBWXDBMNHGCK-FQEVSTJZSA-N 0.000 claims 1
- QSATVYVNCXNSPW-QFIPXVFZSA-N 4-[[(2S)-1-hydroxy-3-naphthalen-2-ylpropan-2-yl]amino]-3-(6-imidazol-1-yl-4-methyl-1H-benzimidazol-2-yl)-1H-pyridin-2-one Chemical compound C=1C=2NC(C=3C(NC=CC=3N[C@H](CO)CC=3C=C4C=CC=CC4=CC=3)=O)=NC=2C(C)=CC=1N1C=CN=C1 QSATVYVNCXNSPW-QFIPXVFZSA-N 0.000 claims 1
- VULKTEGKCCHBBY-IBGZPJMESA-N 4-[[(2S)-1-hydroxy-3-phenylpropan-2-yl]amino]-3-(4-methyl-6-morpholin-4-yl-1H-benzimidazol-2-yl)-1H-pyridin-2-one Chemical compound C([C@@H](CO)NC1=C(C(NC=C1)=O)C=1NC=2C=C(C=C(C=2N=1)C)N1CCOCC1)C1=CC=CC=C1 VULKTEGKCCHBBY-IBGZPJMESA-N 0.000 claims 1
- XBNXAXRVKFHSSL-QFIPXVFZSA-N 4-[[(2S)-1-hydroxy-3-phenylpropan-2-yl]amino]-3-[4-methyl-6-(2-morpholin-4-ylethylamino)-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C=1C=2NC(C=3C(NC=CC=3N[C@H](CO)CC=3C=CC=CC=3)=O)=NC=2C(C)=CC=1NCCN1CCOCC1 XBNXAXRVKFHSSL-QFIPXVFZSA-N 0.000 claims 1
- DWXRRSODJNHKQF-FQEVSTJZSA-N 4-[[(2S)-1-hydroxy-3-phenylpropan-2-yl]amino]-3-[4-methyl-6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C1CN(C)CCN1C1=CC(C)=C(N=C(N2)C=3C(NC=CC=3N[C@H](CO)CC=3C=CC=CC=3)=O)C2=C1 DWXRRSODJNHKQF-FQEVSTJZSA-N 0.000 claims 1
- RHIFVNRZXJLERW-QFIPXVFZSA-N 4-[[(2S)-1-hydroxy-3-phenylpropan-2-yl]amino]-3-[4-methyl-6-(4-propan-2-ylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C1CN(C(C)C)CCN1C1=CC(C)=C(N=C(N2)C=3C(NC=CC=3N[C@H](CO)CC=3C=CC=CC=3)=O)C2=C1 RHIFVNRZXJLERW-QFIPXVFZSA-N 0.000 claims 1
- XSHAQUDGMYHMSJ-JOCHJYFZSA-N 4-[[(2S)-2-(3-bromo-4-methoxyphenyl)-2-hydroxyethyl]amino]-3-[4-methyl-6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C1=C(Br)C(OC)=CC=C1[C@H](O)CNC1=C(C=2NC3=CC(=CC(C)=C3N=2)N2CCN(C)CC2)C(=O)NC=C1 XSHAQUDGMYHMSJ-JOCHJYFZSA-N 0.000 claims 1
- DNTQJDXWGFMNLI-OPAMFIHVSA-N 4-[[(2S)-2-(3-bromo-4-methoxyphenyl)-2-hydroxyethyl]amino]-3-[4-methyl-6-[(2R)-2-methylmorpholin-4-yl]-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C1=C(Br)C(OC)=CC=C1[C@H](O)CNC1=C(C=2NC3=CC(=CC(C)=C3N=2)N2C[C@@H](C)OCC2)C(=O)NC=C1 DNTQJDXWGFMNLI-OPAMFIHVSA-N 0.000 claims 1
- DNTQJDXWGFMNLI-KSFYIVLOSA-N 4-[[(2S)-2-(3-bromo-4-methoxyphenyl)-2-hydroxyethyl]amino]-3-[4-methyl-6-[(2S)-2-methylmorpholin-4-yl]-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C1=C(Br)C(OC)=CC=C1[C@H](O)CNC1=C(C=2NC3=CC(=CC(C)=C3N=2)N2C[C@H](C)OCC2)C(=O)NC=C1 DNTQJDXWGFMNLI-KSFYIVLOSA-N 0.000 claims 1
- XTGIVFQBEPPGGX-PGRDOPGGSA-N 4-[[(2S)-2-(3-bromo-4-methoxyphenyl)-2-hydroxyethyl]amino]-3-[6-[(2R)-2-(fluoromethyl)morpholin-4-yl]-4-methyl-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C1=C(Br)C(OC)=CC=C1[C@H](O)CNC1=C(C=2NC3=CC(=CC(C)=C3N=2)N2C[C@H](CF)OCC2)C(=O)NC=C1 XTGIVFQBEPPGGX-PGRDOPGGSA-N 0.000 claims 1
- LUSNIDFBBMXWAZ-XMSQKQJNSA-N 4-[[(2S)-2-(3-bromo-4-methoxyphenyl)-2-hydroxyethyl]amino]-3-[6-[(2R)-2-(hydroxymethyl)morpholin-4-yl]-4-methyl-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C1=C(Br)C(OC)=CC=C1[C@H](O)CNC1=C(C=2NC3=CC(=CC(C)=C3N=2)N2C[C@H](CO)OCC2)C(=O)NC=C1 LUSNIDFBBMXWAZ-XMSQKQJNSA-N 0.000 claims 1
- ODUJFBNSLMAOSE-AUSIDOKSSA-N 4-[[(2S)-2-(3-bromo-4-methoxyphenyl)-2-hydroxyethyl]amino]-3-[6-[(2R)-2-(methoxymethyl)morpholin-4-yl]-4-methyl-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C1CO[C@@H](COC)CN1C1=CC(C)=C(N=C(N2)C=3C(NC=CC=3NC[C@@H](O)C=3C=C(Br)C(OC)=CC=3)=O)C2=C1 ODUJFBNSLMAOSE-AUSIDOKSSA-N 0.000 claims 1
- XTGIVFQBEPPGGX-XMSQKQJNSA-N 4-[[(2S)-2-(3-bromo-4-methoxyphenyl)-2-hydroxyethyl]amino]-3-[6-[(2S)-2-(fluoromethyl)morpholin-4-yl]-4-methyl-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C1=C(Br)C(OC)=CC=C1[C@H](O)CNC1=C(C=2NC3=CC(=CC(C)=C3N=2)N2C[C@@H](CF)OCC2)C(=O)NC=C1 XTGIVFQBEPPGGX-XMSQKQJNSA-N 0.000 claims 1
- ODUJFBNSLMAOSE-WMZHIEFXSA-N 4-[[(2S)-2-(3-bromo-4-methoxyphenyl)-2-hydroxyethyl]amino]-3-[6-[(2S)-2-(methoxymethyl)morpholin-4-yl]-4-methyl-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C1CO[C@H](COC)CN1C1=CC(C)=C(N=C(N2)C=3C(NC=CC=3NC[C@@H](O)C=3C=C(Br)C(OC)=CC=3)=O)C2=C1 ODUJFBNSLMAOSE-WMZHIEFXSA-N 0.000 claims 1
- JIADGRLHJMOUEK-HSZRJFAPSA-N 4-[[(2S)-2-(3-bromo-4-methoxyphenyl)-2-hydroxyethyl]amino]-3-[6-[4-(2-hydroxyethyl)piperazin-1-yl]-4-methyl-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C1=C(Br)C(OC)=CC=C1[C@H](O)CNC1=C(C=2NC3=CC(=CC(C)=C3N=2)N2CCN(CCO)CC2)C(=O)NC=C1 JIADGRLHJMOUEK-HSZRJFAPSA-N 0.000 claims 1
- SQNXDJMPLAKIID-HXUWFJFHSA-N 4-[[(2S)-2-(3-bromophenyl)-2-hydroxyethyl]amino]-3-(6-imidazol-1-yl-4-methyl-1H-benzimidazol-2-yl)-1H-pyridin-2-one Chemical compound C1([C@H](O)CNC2=C(C(NC=C2)=O)C=2NC=3C=C(C=C(C=3N=2)C)N2C=NC=C2)=CC=CC(Br)=C1 SQNXDJMPLAKIID-HXUWFJFHSA-N 0.000 claims 1
- ONIBKFKEUOBONC-OPAMFIHVSA-N 4-[[(2S)-2-(3-chloro-4-methoxyphenyl)-2-hydroxyethyl]amino]-3-[4-methyl-6-[(2R)-2-methylmorpholin-4-yl]-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C1=C(Cl)C(OC)=CC=C1[C@H](O)CNC1=C(C=2NC3=CC(=CC(C)=C3N=2)N2C[C@@H](C)OCC2)C(=O)NC=C1 ONIBKFKEUOBONC-OPAMFIHVSA-N 0.000 claims 1
- ONIBKFKEUOBONC-KSFYIVLOSA-N 4-[[(2S)-2-(3-chloro-4-methoxyphenyl)-2-hydroxyethyl]amino]-3-[4-methyl-6-[(2S)-2-methylmorpholin-4-yl]-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C1=C(Cl)C(OC)=CC=C1[C@H](O)CNC1=C(C=2NC3=CC(=CC(C)=C3N=2)N2C[C@H](C)OCC2)C(=O)NC=C1 ONIBKFKEUOBONC-KSFYIVLOSA-N 0.000 claims 1
- XNQQOBWDWJLPKE-PGRDOPGGSA-N 4-[[(2S)-2-(3-chloro-4-methoxyphenyl)-2-hydroxyethyl]amino]-3-[6-[(2R)-2-(fluoromethyl)morpholin-4-yl]-4-methyl-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C1=C(Cl)C(OC)=CC=C1[C@H](O)CNC1=C(C=2NC3=CC(=CC(C)=C3N=2)N2C[C@H](CF)OCC2)C(=O)NC=C1 XNQQOBWDWJLPKE-PGRDOPGGSA-N 0.000 claims 1
- RJOLTVNZKRBSOZ-XMSQKQJNSA-N 4-[[(2S)-2-(3-chloro-4-methoxyphenyl)-2-hydroxyethyl]amino]-3-[6-[(2R)-2-(hydroxymethyl)morpholin-4-yl]-4-methyl-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C1=C(Cl)C(OC)=CC=C1[C@H](O)CNC1=C(C=2NC3=CC(=CC(C)=C3N=2)N2C[C@H](CO)OCC2)C(=O)NC=C1 RJOLTVNZKRBSOZ-XMSQKQJNSA-N 0.000 claims 1
- PKNHVWJAADMUFX-AUSIDOKSSA-N 4-[[(2S)-2-(3-chloro-4-methoxyphenyl)-2-hydroxyethyl]amino]-3-[6-[(2R)-2-(methoxymethyl)morpholin-4-yl]-4-methyl-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C1CO[C@@H](COC)CN1C1=CC(C)=C(N=C(N2)C=3C(NC=CC=3NC[C@@H](O)C=3C=C(Cl)C(OC)=CC=3)=O)C2=C1 PKNHVWJAADMUFX-AUSIDOKSSA-N 0.000 claims 1
- XNQQOBWDWJLPKE-XMSQKQJNSA-N 4-[[(2S)-2-(3-chloro-4-methoxyphenyl)-2-hydroxyethyl]amino]-3-[6-[(2S)-2-(fluoromethyl)morpholin-4-yl]-4-methyl-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C1=C(Cl)C(OC)=CC=C1[C@H](O)CNC1=C(C=2NC3=CC(=CC(C)=C3N=2)N2C[C@@H](CF)OCC2)C(=O)NC=C1 XNQQOBWDWJLPKE-XMSQKQJNSA-N 0.000 claims 1
- RJOLTVNZKRBSOZ-PGRDOPGGSA-N 4-[[(2S)-2-(3-chloro-4-methoxyphenyl)-2-hydroxyethyl]amino]-3-[6-[(2S)-2-(hydroxymethyl)morpholin-4-yl]-4-methyl-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound COc1ccc(cc1Cl)[C@H](O)CNc1cc[nH]c(=O)c1-c1nc2c(C)cc(cc2[nH]1)N1CCO[C@H](CO)C1 RJOLTVNZKRBSOZ-PGRDOPGGSA-N 0.000 claims 1
- PKNHVWJAADMUFX-WMZHIEFXSA-N 4-[[(2S)-2-(3-chloro-4-methoxyphenyl)-2-hydroxyethyl]amino]-3-[6-[(2S)-2-(methoxymethyl)morpholin-4-yl]-4-methyl-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C1CO[C@H](COC)CN1C1=CC(C)=C(N=C(N2)C=3C(NC=CC=3NC[C@@H](O)C=3C=C(Cl)C(OC)=CC=3)=O)C2=C1 PKNHVWJAADMUFX-WMZHIEFXSA-N 0.000 claims 1
- GAUMNPIAVGVDBX-HSZRJFAPSA-N 4-[[(2S)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]-3-[4-methyl-6-(2-morpholin-4-ylethoxy)-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C=1C=2NC(C=3C(NC=CC=3NC[C@@H](O)C=3C=C(Cl)C=CC=3)=O)=NC=2C(C)=CC=1OCCN1CCOCC1 GAUMNPIAVGVDBX-HSZRJFAPSA-N 0.000 claims 1
- IIJGLRWTELJRPH-OPAMFIHVSA-N 4-[[(2S)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]-3-[4-methyl-6-[(2R)-2-methylmorpholin-4-yl]-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C1CO[C@H](C)CN1C1=CC(C)=C(N=C(N2)C=3C(NC=CC=3NC[C@@H](O)C=3C=C(Cl)C=CC=3)=O)C2=C1 IIJGLRWTELJRPH-OPAMFIHVSA-N 0.000 claims 1
- YNIARPVUHAXJQZ-LJQANCHMSA-N 4-[[(2S)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]-3-[6-(2-hydroxyethoxy)-4-methyl-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C1([C@H](O)CNC2=C(C(NC=C2)=O)C=2NC=3C=C(OCCO)C=C(C=3N=2)C)=CC=CC(Cl)=C1 YNIARPVUHAXJQZ-LJQANCHMSA-N 0.000 claims 1
- CJCXXSGEMIIROV-HXUWFJFHSA-N 4-[[(2S)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]-3-[6-(2-methoxyethoxy)-4-methyl-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C1([C@H](O)CNC2=C(C(NC=C2)=O)C2=NC3=C(C)C=C(C=C3N2)OCCOC)=CC=CC(Cl)=C1 CJCXXSGEMIIROV-HXUWFJFHSA-N 0.000 claims 1
- KPFSRAAWPJUHQV-OAQYLSRUSA-N 4-[[(2S)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]-3-[6-(5,6-dihydro-4H-pyrimidin-1-yl)-4-methyl-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C1([C@H](O)CNC2=C(C(NC=C2)=O)C=2NC=3C=C(C=C(C=3N=2)C)N2C=NCCC2)=CC=CC(Cl)=C1 KPFSRAAWPJUHQV-OAQYLSRUSA-N 0.000 claims 1
- WHJWUUJEQQJCLJ-SIKLNZKXSA-N 4-[[(2S)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]-3-[6-[(2R)-2-(fluoromethyl)morpholin-4-yl]-4-methyl-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C1([C@H](O)CNC2=C(C(NC=C2)=O)C=2NC=3C=C(C=C(C=3N=2)C)N2C[C@H](CF)OCC2)=CC=CC(Cl)=C1 WHJWUUJEQQJCLJ-SIKLNZKXSA-N 0.000 claims 1
- HHGSXZXKYKUWGJ-DENIHFKCSA-N 4-[[(2S)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]-3-[6-[(2R)-2-(hydroxymethyl)morpholin-4-yl]-4-methyl-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C1([C@H](O)CNC2=C(C(NC=C2)=O)C=2NC=3C=C(C=C(C=3N=2)C)N2C[C@H](CO)OCC2)=CC=CC(Cl)=C1 HHGSXZXKYKUWGJ-DENIHFKCSA-N 0.000 claims 1
- UHOVHYKNOIFMRB-NFBKMPQASA-N 4-[[(2S)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]-3-[6-[(2R)-2-(methoxymethyl)morpholin-4-yl]-4-methyl-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C1CO[C@@H](COC)CN1C1=CC(C)=C(N=C(N2)C=3C(NC=CC=3NC[C@@H](O)C=3C=C(Cl)C=CC=3)=O)C2=C1 UHOVHYKNOIFMRB-NFBKMPQASA-N 0.000 claims 1
- WHJWUUJEQQJCLJ-DENIHFKCSA-N 4-[[(2S)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]-3-[6-[(2S)-2-(fluoromethyl)morpholin-4-yl]-4-methyl-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C1([C@H](O)CNC2=C(C(NC=C2)=O)C=2NC=3C=C(C=C(C=3N=2)C)N2C[C@@H](CF)OCC2)=CC=CC(Cl)=C1 WHJWUUJEQQJCLJ-DENIHFKCSA-N 0.000 claims 1
- HHGSXZXKYKUWGJ-SIKLNZKXSA-N 4-[[(2S)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]-3-[6-[(2S)-2-(hydroxymethyl)morpholin-4-yl]-4-methyl-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound Cc1cc(cc2[nH]c(nc12)-c1c(NC[C@@H](O)c2cccc(Cl)c2)cc[nH]c1=O)N1CCO[C@H](CO)C1 HHGSXZXKYKUWGJ-SIKLNZKXSA-N 0.000 claims 1
- AATRIKZDGKCSFA-UZUQRXQVSA-N 4-[[(2S)-2-(7-bromo-2,3-dihydro-1-benzofuran-4-yl)-2-hydroxyethyl]amino]-3-[6-[(2S)-2-(fluoromethyl)morpholin-4-yl]-4-methyl-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C=1C=2NC(C=3C(NC=CC=3NC[C@@H](O)C=3C=4CCOC=4C(Br)=CC=3)=O)=NC=2C(C)=CC=1N1CCO[C@H](CF)C1 AATRIKZDGKCSFA-UZUQRXQVSA-N 0.000 claims 1
- LQRBWXDBMNHGCK-HXUWFJFHSA-N 4-[[(2S)-2-hydroxy-2-phenylethyl]amino]-3-(6-imidazol-1-yl-4-methyl-1H-benzimidazol-2-yl)-1H-pyridin-2-one Chemical compound C1([C@H](O)CNC2=C(C(NC=C2)=O)C=2NC=3C=C(C=C(C=3N=2)C)N2C=NC=C2)=CC=CC=C1 LQRBWXDBMNHGCK-HXUWFJFHSA-N 0.000 claims 1
- FSDYMRXZPHZFJS-UHFFFAOYSA-N 4-[[2-(3-bromo-4-methoxyphenyl)-2-hydroxyethyl]amino]-3-(4-methyl-6-morpholin-4-yl-1H-benzimidazol-2-yl)-1H-pyridin-2-one Chemical compound C1=C(Br)C(OC)=CC=C1C(O)CNC1=C(C=2NC3=CC(=CC(C)=C3N=2)N2CCOCC2)C(=O)NC=C1 FSDYMRXZPHZFJS-UHFFFAOYSA-N 0.000 claims 1
- PZSACZRLMBGKSF-VEXWJQHLSA-N 4-[[2-(3-bromo-4-methoxyphenyl)-2-hydroxyethyl]amino]-3-[4-methyl-6-[(2S)-2-morpholin-4-ylpropoxy]-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound BrC=1C=C(C=CC1OC)C(CNC1=C(C(NC=C1)=O)C1=NC2=C(N1)C=C(C=C2C)OC[C@H](C)N2CCOCC2)O PZSACZRLMBGKSF-VEXWJQHLSA-N 0.000 claims 1
- IMMXVSIPHLGTTG-UHFFFAOYSA-N 4-[[2-(3-bromo-4-methoxyphenyl)-2-hydroxyethyl]amino]-3-[6-[4-(3-fluoropropyl)piperazin-1-yl]-4-methyl-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C1=C(Br)C(OC)=CC=C1C(O)CNC1=C(C=2NC3=CC(=CC(C)=C3N=2)N2CCN(CCCF)CC2)C(=O)NC=C1 IMMXVSIPHLGTTG-UHFFFAOYSA-N 0.000 claims 1
- FOYPTSVQLMKMNX-UHFFFAOYSA-N 4-[[2-(3-bromophenyl)-2-fluoroethyl]amino]-3-(6-imidazol-1-yl-4-methyl-1H-benzimidazol-2-yl)-1H-pyridin-2-one Chemical compound N=1C=2C(C)=CC(N3C=NC=C3)=CC=2NC=1C(C(NC=C1)=O)=C1NCC(F)C1=CC=CC(Br)=C1 FOYPTSVQLMKMNX-UHFFFAOYSA-N 0.000 claims 1
- MQPZCABORBJAFW-UHFFFAOYSA-N 4-[[2-(3-chloro-4-fluorophenyl)-2-hydroxyethyl]amino]-3-(4-methyl-6-morpholin-4-yl-1H-benzimidazol-2-yl)-1H-pyridin-2-one Chemical compound N=1C=2C(C)=CC(N3CCOCC3)=CC=2NC=1C(C(NC=C1)=O)=C1NCC(O)C1=CC=C(F)C(Cl)=C1 MQPZCABORBJAFW-UHFFFAOYSA-N 0.000 claims 1
- MQKSVRLGJFYTRI-UHFFFAOYSA-N 4-[[2-(3-chloro-4-fluorophenyl)-2-hydroxyethyl]amino]-3-(4-methyl-6-piperazin-1-yl-1H-benzimidazol-2-yl)-1H-pyridin-2-one Chemical compound N=1C=2C(C)=CC(N3CCNCC3)=CC=2NC=1C(C(NC=C1)=O)=C1NCC(O)C1=CC=C(F)C(Cl)=C1 MQKSVRLGJFYTRI-UHFFFAOYSA-N 0.000 claims 1
- LGLHDKFGXZEGKW-UHFFFAOYSA-N 4-[[2-(3-chloro-4-fluorophenyl)-2-hydroxyethyl]amino]-3-[6-[4-(3-fluoropropyl)piperazin-1-yl]-4-methyl-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound N=1C=2C(C)=CC(N3CCN(CCCF)CC3)=CC=2NC=1C(C(NC=C1)=O)=C1NCC(O)C1=CC=C(F)C(Cl)=C1 LGLHDKFGXZEGKW-UHFFFAOYSA-N 0.000 claims 1
- IYAZTZOPWLFGSM-UHFFFAOYSA-N 4-[[2-(3-chloro-4-methoxyphenyl)-2-hydroxyethyl]amino]-3-(4-methyl-6-morpholin-4-yl-1H-benzimidazol-2-yl)-1H-pyridin-2-one Chemical compound C1=C(Cl)C(OC)=CC=C1C(O)CNC1=C(C=2NC3=CC(=CC(C)=C3N=2)N2CCOCC2)C(=O)NC=C1 IYAZTZOPWLFGSM-UHFFFAOYSA-N 0.000 claims 1
- VTMIHYCOXBGSOX-UHFFFAOYSA-N 4-[[2-(3-chloro-4-methoxyphenyl)-2-hydroxyethyl]amino]-3-[6-[4-(3-fluoropropyl)piperazin-1-yl]-4-methyl-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound C1=C(Cl)C(OC)=CC=C1C(O)CNC1=C(C=2NC3=CC(=CC(C)=C3N=2)N2CCN(CCCF)CC2)C(=O)NC=C1 VTMIHYCOXBGSOX-UHFFFAOYSA-N 0.000 claims 1
- MZFRECTUVDMWLE-UHFFFAOYSA-N 4-[[2-(3-chloro-4-methylsulfanylphenyl)-2-hydroxyethyl]amino]-3-(4-methyl-6-piperazin-1-yl-1H-benzimidazol-2-yl)-1H-pyridin-2-one Chemical compound C1=C(Cl)C(SC)=CC=C1C(O)CNC1=C(C=2NC3=CC(=CC(C)=C3N=2)N2CCNCC2)C(=O)NC=C1 MZFRECTUVDMWLE-UHFFFAOYSA-N 0.000 claims 1
- GLPQSWLXLBIVRM-UHFFFAOYSA-N 4-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]-3-(6-imidazol-1-yl-1H-benzimidazol-2-yl)-1H-pyridin-2-one Chemical compound C=1C=CC(Cl)=CC=1C(O)CNC=1C=CNC(=O)C=1C(NC1=C2)=NC1=CC=C2N1C=CN=C1 GLPQSWLXLBIVRM-UHFFFAOYSA-N 0.000 claims 1
- UIBLHEZWESDKHO-UHFFFAOYSA-N 4-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]-3-[4-methyl-6-[4-(2-thiomorpholin-4-ylacetyl)piperazin-1-yl]-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound N=1C=2C(C)=CC(N3CCN(CC3)C(=O)CN3CCSCC3)=CC=2NC=1C(C(NC=C1)=O)=C1NCC(O)C1=CC=CC(Cl)=C1 UIBLHEZWESDKHO-UHFFFAOYSA-N 0.000 claims 1
- QLBZNPSNLVNWIT-UHFFFAOYSA-N 4-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]-3-[4-methyl-6-[4-(3,3,3-trifluoropropyl)piperazin-1-yl]-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound N=1C=2C(C)=CC(N3CCN(CCC(F)(F)F)CC3)=CC=2NC=1C(C(NC=C1)=O)=C1NCC(O)C1=CC=CC(Cl)=C1 QLBZNPSNLVNWIT-UHFFFAOYSA-N 0.000 claims 1
- BDECAGGTSQFWTL-UHFFFAOYSA-N 4-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]-3-[4-methyl-6-[4-(3,4,4-trifluorobut-3-enyl)piperazin-1-yl]-1H-benzimidazol-2-yl]-1H-pyridin-2-one Chemical compound N=1C=2C(C)=CC(N3CCN(CCC(F)=C(F)F)CC3)=CC=2NC=1C(C(NC=C1)=O)=C1NCC(O)C1=CC=CC(Cl)=C1 BDECAGGTSQFWTL-UHFFFAOYSA-N 0.000 claims 1
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- RQZAXGRLVPAYTJ-GQFGMJRRSA-N megestrol acetate Chemical compound C1=C(C)C2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)C)[C@@]1(C)CC2 RQZAXGRLVPAYTJ-GQFGMJRRSA-N 0.000 claims 1
- SGDBTWWWUNNDEQ-LBPRGKRZSA-N melphalan Chemical compound OC(=O)[C@@H](N)CC1=CC=C(N(CCCl)CCCl)C=C1 SGDBTWWWUNNDEQ-LBPRGKRZSA-N 0.000 claims 1
- 229960001924 melphalan Drugs 0.000 claims 1
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- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
- CFCUWKMKBJTWLW-BKHRDMLASA-N mithramycin Chemical compound O([C@@H]1C[C@@H](O[C@H](C)[C@H]1O)OC=1C=C2C=C3C[C@H]([C@@H](C(=O)C3=C(O)C2=C(O)C=1C)O[C@@H]1O[C@H](C)[C@@H](O)[C@H](O[C@@H]2O[C@H](C)[C@H](O)[C@H](O[C@@H]3O[C@H](C)[C@@H](O)[C@@](C)(O)C3)C2)C1)[C@H](OC)C(=O)[C@@H](O)[C@@H](C)O)[C@H]1C[C@@H](O)[C@H](O)[C@@H](C)O1 CFCUWKMKBJTWLW-BKHRDMLASA-N 0.000 claims 1
- 229960004857 mitomycin Drugs 0.000 claims 1
- 150000002780 morpholines Chemical class 0.000 claims 1
- 125000006203 morpholinoethyl group Chemical group [H]C([H])(*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims 1
- BLCLNMBMMGCOAS-UHFFFAOYSA-N n-[1-[[1-[[1-[[1-[[1-[[1-[[1-[2-[(carbamoylamino)carbamoyl]pyrrolidin-1-yl]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-[(2-methylpropan-2-yl)oxy]-1-oxopropan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amin Chemical compound C1CCC(C(=O)NNC(N)=O)N1C(=O)C(CCCN=C(N)N)NC(=O)C(CC(C)C)NC(=O)C(COC(C)(C)C)NC(=O)C(NC(=O)C(CO)NC(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C(CC=1NC=NC=1)NC(=O)C1NC(=O)CC1)CC1=CC=C(O)C=C1 BLCLNMBMMGCOAS-UHFFFAOYSA-N 0.000 claims 1
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- XUWVIABDWDTJRZ-UHFFFAOYSA-N propan-2-ylazanide Chemical compound CC(C)[NH-] XUWVIABDWDTJRZ-UHFFFAOYSA-N 0.000 claims 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims 1
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- 229960004622 raloxifene Drugs 0.000 claims 1
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- 150000003839 salts Chemical class 0.000 claims 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
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- 229960001278 teniposide Drugs 0.000 claims 1
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- 229960005026 toremifene Drugs 0.000 claims 1
- XFCLJVABOIYOMF-QPLCGJKRSA-N toremifene Chemical compound C1=CC(OCCN(C)C)=CC=C1C(\C=1C=CC=CC=1)=C(\CCCl)C1=CC=CC=C1 XFCLJVABOIYOMF-QPLCGJKRSA-N 0.000 claims 1
- 239000002525 vasculotropin inhibitor Substances 0.000 claims 1
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 claims 1
- 229960004528 vincristine Drugs 0.000 claims 1
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 claims 1
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US27932701P | 2001-03-28 | 2001-03-28 | |
PCT/US2002/009402 WO2002079192A1 (en) | 2001-03-28 | 2002-03-26 | Novel tyrosine kinase inhibitors |
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JP2004534010A JP2004534010A (ja) | 2004-11-11 |
JP2004534010A5 true JP2004534010A5 (hr) | 2005-12-22 |
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JP2002577817A Withdrawn JP2004534010A (ja) | 2001-03-28 | 2002-03-26 | 新規なチロシンキナーゼ阻害剤 |
Country Status (25)
Country | Link |
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EP (1) | EP1381598A4 (hr) |
JP (1) | JP2004534010A (hr) |
KR (1) | KR20030083016A (hr) |
CN (1) | CN1514833A (hr) |
AR (1) | AR035804A1 (hr) |
BG (1) | BG108206A (hr) |
BR (1) | BR0208373A (hr) |
CA (1) | CA2442428A1 (hr) |
CZ (1) | CZ20032615A3 (hr) |
EE (1) | EE200300475A (hr) |
GE (1) | GEP20053660B (hr) |
HR (1) | HRP20030844A2 (hr) |
HU (1) | HUP0400323A2 (hr) |
IL (1) | IL158041A0 (hr) |
IS (1) | IS6968A (hr) |
MX (1) | MXPA03008690A (hr) |
NO (1) | NO20034308L (hr) |
PE (1) | PE20021015A1 (hr) |
PL (1) | PL373300A1 (hr) |
RU (1) | RU2003131693A (hr) |
SK (1) | SK12002003A3 (hr) |
UY (1) | UY27234A1 (hr) |
WO (1) | WO2002079192A1 (hr) |
YU (1) | YU84603A (hr) |
ZA (1) | ZA200307466B (hr) |
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JP2005532368A (ja) * | 2002-06-12 | 2005-10-27 | アボット・ラボラトリーズ | メラニン濃縮ホルモン受容体の拮抗薬 |
WO2004050033A2 (en) * | 2002-12-02 | 2004-06-17 | Arqule, Inc. | Method of treating cancers |
EP1581539A4 (en) * | 2003-01-03 | 2007-09-19 | Bristol Myers Squibb Co | NEW TYROSINE KINASE HEMMER |
WO2004069160A2 (en) * | 2003-01-28 | 2004-08-19 | Smithkline Beecham Corporation | Chemical compounds |
US7312215B2 (en) | 2003-07-29 | 2007-12-25 | Bristol-Myers Squibb Company | Benzimidazole C-2 heterocycles as kinase inhibitors |
AU2004268621C1 (en) * | 2003-08-29 | 2011-08-18 | Exelixis, Inc. | c-Kit modulators and methods of use |
US20050075358A1 (en) * | 2003-10-06 | 2005-04-07 | Carboni Joan M. | Methods for treating IGF1R-inhibitor induced hyperglycemia |
DE102004010207A1 (de) * | 2004-03-02 | 2005-09-15 | Aventis Pharma S.A. | Neue 4-Benzimidazol-2-yl-pyridazin-3-on-Derivate |
DK1740591T3 (da) | 2004-04-02 | 2009-10-26 | Osi Pharm Inc | Heterobicykliske proteinkinaseinhibitorer substitueret med en 6,6-biocyclisk ring |
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WO2006130657A2 (en) | 2005-05-31 | 2006-12-07 | Bristol-Myers Squibb Company | Stereoselective reduction process for the preparation of pyrrolotriazine compounds |
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US8093401B2 (en) | 2005-08-04 | 2012-01-10 | Sirtris Pharmaceuticals, Inc. | Sirtuin modulating compounds |
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EP1919905B1 (en) * | 2005-08-29 | 2011-02-23 | Vertex Pharmaceuticals Incorporated | 3,5-disubstituted pyrid-2-ones useful as inhibitors of tec family of non-recptor tyrosine kinases |
WO2007026720A1 (ja) * | 2005-08-31 | 2007-03-08 | Taisho Pharmaceutical Co., Ltd. | 縮環ピラゾール誘導体 |
US8575164B2 (en) | 2005-12-19 | 2013-11-05 | OSI Pharmaceuticals, LLC | Combination cancer therapy |
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US8063225B2 (en) | 2006-08-14 | 2011-11-22 | Chembridge Corporation | Tricyclic compound derivatives useful in the treatment of neoplastic diseases, inflammatory disorders and immunomodulatory disorders |
WO2008022747A1 (en) * | 2006-08-21 | 2008-02-28 | F. Hoffmann-La Roche Ag | Tricyclic lactam derivatives, their manufacture and use as pharmaceutical agents |
WO2008025526A1 (en) * | 2006-08-31 | 2008-03-06 | F. Hoffmann-La Roche Ag | Indole derivatives, their manufacture and use as pharmaceutical agents |
EP2559771A3 (en) | 2007-05-17 | 2013-06-12 | Bristol-Myers Squibb Company | Biomarkers and methods for determining sensitivity to insulin growth factor-1 receptor modulators |
TW200916472A (en) | 2007-06-20 | 2009-04-16 | Sirtris Pharmaceuticals Inc | Sirtuin modulating compounds |
EP2170859A1 (en) | 2007-06-25 | 2010-04-07 | F. Hoffmann-Roche AG | Benzimidazole amido derivatives as kinase inhibitors |
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EP2294065B1 (en) | 2008-01-22 | 2014-03-19 | Vernalis (R&D) Ltd. | Indolyl-pyridone derivatives having checkpoint kinase 1 inhibitory activity |
ES2396613T3 (es) | 2008-05-19 | 2013-02-22 | OSI Pharmaceuticals, LLC | Imidazopirazinas e imidazotriazinas sustituidas |
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DE102010001064A1 (de) * | 2009-03-18 | 2010-09-23 | Bayer Schering Pharma Aktiengesellschaft | Substituierte 2-Acetamido-5-Aryl-1,2,4-triazolone und deren Verwendung |
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MA34591B1 (fr) * | 2010-10-06 | 2013-10-02 | Glaxosmithkline Llc | Dérivés de benzimidazole utilisés comme inhibiteurs de pi3 kinase |
WO2012061169A1 (en) * | 2010-11-01 | 2012-05-10 | Boehringer Ingelheim International Gmbh | Benzimidazole inhibitors of leukotriene production |
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US9662311B2 (en) | 2013-06-21 | 2017-05-30 | Zenith Epigenetics Ltd. | Substituted bicyclic compounds as bromodomain inhibitors |
BR112015031073B1 (pt) | 2013-06-21 | 2022-11-29 | Zenith Epigenetics Ltd | Compostos inibidores bicíclicos de bromodomínio e composição farmacêutica contendo os referidos compostos |
WO2015015318A2 (en) | 2013-07-31 | 2015-02-05 | Zenith Epigenetics Corp. | Novel quinazolinones as bromodomain inhibitors |
CN103936719A (zh) * | 2014-05-14 | 2014-07-23 | 中国药科大学 | 苯并咪唑类衍生物制备方法及用途 |
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US6162804A (en) * | 1997-09-26 | 2000-12-19 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
EE04813B1 (et) * | 1999-06-23 | 2007-04-16 | Aventis Pharma Deutschland Gmbh | Asendatud bensimidasoolid, nende saamine ning kasutamine ravimi valmistamiseks, mis on ette nähtud NFkB aktiivsuse suurenemisest tingitud haiguste profülaktikaks ja raviks |
US7081454B2 (en) * | 2001-03-28 | 2006-07-25 | Bristol-Myers Squibb Co. | Tyrosine kinase inhibitors |
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- 2002-03-26 WO PCT/US2002/009402 patent/WO2002079192A1/en active Application Filing
- 2002-03-26 HU HU0400323A patent/HUP0400323A2/hu unknown
- 2002-03-26 MX MXPA03008690A patent/MXPA03008690A/es unknown
- 2002-03-26 EE EEP200300475A patent/EE200300475A/xx unknown
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- 2002-03-26 CN CNA028105168A patent/CN1514833A/zh active Pending
- 2002-03-26 GE GE5363A patent/GEP20053660B/en unknown
- 2002-03-26 JP JP2002577817A patent/JP2004534010A/ja not_active Withdrawn
- 2002-03-26 BR BR0208373-6A patent/BR0208373A/pt not_active IP Right Cessation
- 2002-03-26 YU YU84603A patent/YU84603A/sh unknown
- 2002-03-26 CA CA002442428A patent/CA2442428A1/en not_active Abandoned
- 2002-03-26 SK SK12002003A patent/SK12002003A3/sk not_active Application Discontinuation
- 2002-03-26 IL IL15804102A patent/IL158041A0/xx unknown
- 2002-03-26 EP EP02723631A patent/EP1381598A4/en not_active Withdrawn
- 2002-03-26 RU RU2003131693/04A patent/RU2003131693A/ru not_active Application Discontinuation
- 2002-03-26 CZ CZ20032615A patent/CZ20032615A3/cs unknown
- 2002-03-27 UY UY27234A patent/UY27234A1/es not_active Application Discontinuation
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- 2002-03-27 AR ARP020101167A patent/AR035804A1/es not_active Application Discontinuation
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- 2003-09-26 BG BG108206A patent/BG108206A/bg unknown
- 2003-09-26 NO NO20034308A patent/NO20034308L/no not_active Application Discontinuation
- 2003-10-17 HR HR20030844A patent/HRP20030844A2/hr not_active Application Discontinuation
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