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- Withdrawn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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| AU2003243497A1 (en) * | 2002-06-12 | 2003-12-31 | Millennium Pharmaceuticals, Inc. | Antagonists of melanin concentrating hormone receptor |
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| WO2004063151A2 (en) | 2003-01-03 | 2004-07-29 | Bristol-Myers Squibb Company | Novel tyrosine kinase inhibitors |
| US7329678B2 (en) * | 2003-01-28 | 2008-02-12 | Smithkline Beecham Corporation | Chemical compounds |
| US7312215B2 (en) | 2003-07-29 | 2007-12-25 | Bristol-Myers Squibb Company | Benzimidazole C-2 heterocycles as kinase inhibitors |
| WO2005020921A2 (en) * | 2003-08-29 | 2005-03-10 | Exelixis, Inc. | C-kit modulators and methods of use |
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| US7582634B2 (en) | 2005-02-18 | 2009-09-01 | Wyeth | 7-substituted imidazo[4,5-c]pyridine antagonists of gonadotropin releasing hormone receptor |
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| ATE528302T1 (de) | 2005-08-29 | 2011-10-15 | Vertex Pharma | 3,5-disubstituierte pyrid-2-one, die als hemmer der tec-familie von nicht-rezeptor tyrosin- kinasen nützlich sind |
| DE602006020293D1 (de) * | 2005-08-29 | 2011-04-07 | Vertex Pharma | 3,5-disubstituierte pyrid-2-one, die als hemmer der tec-familie von nicht-rezeptor tyrosin-kinasen nützlich sind |
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| WO2008025526A1 (en) * | 2006-08-31 | 2008-03-06 | F. Hoffmann-La Roche Ag | Indole derivatives, their manufacture and use as pharmaceutical agents |
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| JP2010531316A (ja) * | 2007-06-25 | 2010-09-24 | エフ．ホフマン−ラ ロシュ アーゲー | キナーゼ阻害剤としてのベンズイミダゾールアミド誘導体 |
| EP2065380A1 (en) * | 2007-08-22 | 2009-06-03 | F.Hoffmann-La Roche Ag | Pyridoneamide derivatives as focal adhesion kinase (FAK) inhibitors and their use for the treatment of cancer |
| US7816540B2 (en) * | 2007-12-21 | 2010-10-19 | Hoffmann-La Roche Inc. | Carboxyl- or hydroxyl-substituted benzimidazole derivatives |
| JP5386508B2 (ja) * | 2008-01-22 | 2014-01-15 | ヴァーナリス アールアンドディー リミテッド | インドリル−ピリドン誘導体類 |
| EP2283020B8 (en) | 2008-05-19 | 2012-12-12 | OSI Pharmaceuticals, LLC | Substituted imidazopyr-and imidazotri-azines |
| EA021424B1 (ru) | 2008-12-19 | 2015-06-30 | Сертрис Фармасьютикалз, Инк. | Тиазолопиридиновые соединения, регулирующие сиртуин |
| 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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| EP2435435B1 (en) * | 2009-05-27 | 2014-01-29 | AbbVie Inc. | Pyrimidine inhibitors of kinase activity |
| US20120220594A1 (en) | 2009-10-30 | 2012-08-30 | Bristol-Meyers Squibb Company | Methods for treating cancer in patients having igf-1r inhibitor resistance |
| ES2616238T3 (es) * | 2010-10-06 | 2017-06-12 | Glaxosmithkline Llc, Corporation Service Company | Derivados de bencimidazol como inhibidores de PI3 quinasa |
| JP5789888B2 (ja) * | 2010-11-01 | 2015-10-07 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | ロイコトリエン生成のベンゾイミダゾールインヒビター |
| WO2013056069A1 (en) | 2011-10-13 | 2013-04-18 | Bristol-Myers Squibb Company | Methods for selecting and treating cancer in patients with igf-1r/ir inhibitors |
| WO2015004533A2 (en) | 2013-06-21 | 2015-01-15 | Zenith Epigenetics Corp. | Novel substituted bicyclic compounds as bromodomain inhibitors |
| SG11201510409QA (en) | 2013-06-21 | 2016-01-28 | Zenith Epigenetics Corp | Novel bicyclic bromodomain inhibitors |
| AU2014298051B2 (en) | 2013-07-31 | 2018-11-15 | Zenith Epigenetics Ltd. | 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 |
| CN108064274A (zh) | 2014-07-30 | 2018-05-22 | 耶达研究及发展有限公司 | 用于培养多能干细胞的培养基 |
| WO2016087936A1 (en) | 2014-12-01 | 2016-06-09 | Zenith Epigenetics Corp. | Substituted pyridinones as bromodomain inhibitors |
| CN107207474B (zh) | 2014-12-11 | 2021-05-07 | 恒翼生物医药科技(上海)有限公司 | 被取代的杂环作为溴结构域抑制剂 |
| CA2966450A1 (en) | 2014-12-17 | 2016-06-23 | Olesya KHARENKO | Inhibitors of bromodomains |
| CA2982664A1 (en) * | 2015-04-16 | 2016-10-20 | Merck Patent Gmbh | 3-(1h-benzimidazol-2-yl)-1h-pyridin-2-one derivatives |
| EP3914698B1 (en) | 2019-01-23 | 2024-12-11 | Yeda Research and Development Co. Ltd | Culture media for pluripotent stem cells |
| BR112022022437A2 (pt) | 2020-05-07 | 2023-01-03 | Adorx Therapeutics Ltd | Antagonistas do receptor a2a de adenosina |
| CN117069696B (zh) * | 2023-08-17 | 2024-04-26 | 中国药科大学 | 一种双靶点小分子抑制剂及其制备方法和应用 |
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| US6162804A (en) * | 1997-09-26 | 2000-12-19 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
| KR100718830B1 (ko) * | 1999-06-23 | 2007-05-17 | 사노피-아벤티스 도이칠란트 게엠베하 | 치환된 벤즈이미다졸 및 이의 제조방법 |
| US7081454B2 (en) * | 2001-03-28 | 2006-07-25 | Bristol-Myers Squibb Co. | Tyrosine kinase inhibitors |
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