TW201504224A - 新穎吲哚及吡咯化合物，其製備方法及含有其之醫藥組合物 - Google Patents

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Publication number

TW201504224A

TW201504224A TW103125162A TW103125162A TW201504224A TW 201504224 A TW201504224 A TW 201504224A TW 103125162 A TW103125162 A TW 103125162A TW 103125162 A TW103125162 A TW 103125162A TW 201504224 A TW201504224 A TW 201504224A

Authority

TW

Taiwan

Prior art keywords

methyl

group

compound

phenyl

formula

Prior art date

2013-07-23

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• 238000000034 method Methods 0.000 title claims description 446
• 238000002360 preparation method Methods 0.000 title claims description 339
• 239000008194 pharmaceutical composition Substances 0.000 title claims description 14
• 230000008569 process Effects 0.000 title claims description 10
• 150000003233 pyrroles Chemical class 0.000 title description 2
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title 2
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 title 1
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 410
• 239000003814 drug Substances 0.000 claims abstract description 8
• 229910052757 nitrogen Inorganic materials 0.000 claims description 192
• 229910052739 hydrogen Inorganic materials 0.000 claims description 166
• -1 -NR 7 R 7 ' Chemical group 0.000 claims description 147
• 229910052799 carbon Inorganic materials 0.000 claims description 139
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 108
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 95
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 93
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 89
• 125000003118 aryl group Chemical group 0.000 claims description 82
• 239000002253 acid Substances 0.000 claims description 67
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 47
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 46
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 45
• 239000001257 hydrogen Substances 0.000 claims description 35
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Chemical class C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 30
• 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 28
• 125000000217 alkyl group Chemical group 0.000 claims description 26
• 125000005843 halogen group Chemical group 0.000 claims description 26
• 125000006239 protecting group Chemical group 0.000 claims description 26
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 22
• 238000000746 purification Methods 0.000 claims description 22
• 206010028980 Neoplasm Diseases 0.000 claims description 21
• 238000011282 treatment Methods 0.000 claims description 21
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
• 150000001412 amines Chemical class 0.000 claims description 19
• 201000011510 cancer Diseases 0.000 claims description 18
• 125000004432 carbon atom Chemical group C* 0.000 claims description 16
• 125000001072 heteroaryl group Chemical group 0.000 claims description 16
• 150000003839 salts Chemical class 0.000 claims description 16
• 239000007858 starting material Substances 0.000 claims description 14
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 11
• 125000001424 substituent group Chemical group 0.000 claims description 11
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 9
• 150000002148 esters Chemical class 0.000 claims description 9
• 229910052736 halogen Inorganic materials 0.000 claims description 9
• 150000002367 halogens Chemical class 0.000 claims description 9
• 125000005842 heteroatom Chemical group 0.000 claims description 9
• 150000002431 hydrogen Chemical class 0.000 claims description 9
• 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims description 9
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 8
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• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
• 150000001768 cations Chemical class 0.000 claims description 8
• 238000006243 chemical reaction Methods 0.000 claims description 8
• 229910052760 oxygen Inorganic materials 0.000 claims description 8
• 239000001301 oxygen Substances 0.000 claims description 8
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 8
• 229910052717 sulfur Chemical group 0.000 claims description 8
• 239000011593 sulfur Chemical group 0.000 claims description 8
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 7
• 206010041067 Small cell lung cancer Diseases 0.000 claims description 7
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 7
• 125000000623 heterocyclic group Chemical group 0.000 claims description 7
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• 238000000926 separation method Methods 0.000 claims description 7
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• 125000005605 benzo group Chemical group 0.000 claims description 6
• 125000002619 bicyclic group Chemical group 0.000 claims description 6
• 239000003153 chemical reaction reagent Substances 0.000 claims description 6
• 239000003795 chemical substances by application Substances 0.000 claims description 6
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 6
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
• 125000002950 monocyclic group Chemical group 0.000 claims description 6
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
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• 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 6
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• 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims description 5
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• 206010035226 Plasma cell myeloma Diseases 0.000 claims description 5
• 208000002495 Uterine Neoplasms Diseases 0.000 claims description 5
• 208000032852 chronic lymphocytic leukemia Diseases 0.000 claims description 5
• XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 claims description 5
• 235000011180 diphosphates Nutrition 0.000 claims description 5
• 201000004101 esophageal cancer Diseases 0.000 claims description 5
• 201000007270 liver cancer Diseases 0.000 claims description 5
• 208000014018 liver neoplasm Diseases 0.000 claims description 5
• 208000003747 lymphoid leukemia Diseases 0.000 claims description 5
• 201000001441 melanoma Diseases 0.000 claims description 5
• 201000000050 myeloid neoplasm Diseases 0.000 claims description 5
• 108090000765 processed proteins & peptides Proteins 0.000 claims description 5
• 206010046766 uterine cancer Diseases 0.000 claims description 5
• FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 4
• RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical class C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 4
• 150000007513 acids Chemical class 0.000 claims description 4
• 125000003277 amino group Chemical group 0.000 claims description 4
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
• 238000005859 coupling reaction Methods 0.000 claims description 4
• 208000032839 leukemia Diseases 0.000 claims description 4
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
• 230000000861 pro-apoptotic effect Effects 0.000 claims description 4
• 239000003053 toxin Substances 0.000 claims description 4
• 231100000765 toxin Toxicity 0.000 claims description 4
• 108700012359 toxins Proteins 0.000 claims description 4
• CCDAHKDEKOTDGR-UHFFFAOYSA-N 3-phenoxyazetidine Chemical compound C1NCC1OC1=CC=CC=C1 CCDAHKDEKOTDGR-UHFFFAOYSA-N 0.000 claims description 3
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
• 125000003342 alkenyl group Chemical group 0.000 claims description 3
• 125000003545 alkoxy group Chemical group 0.000 claims description 3
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
• 230000008878 coupling Effects 0.000 claims description 3
• 238000010168 coupling process Methods 0.000 claims description 3
• 238000010511 deprotection reaction Methods 0.000 claims description 3
• 201000010099 disease Diseases 0.000 claims description 3
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
• 238000006467 substitution reaction Methods 0.000 claims description 3
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 2
• 150000000094 1,4-dioxanes Chemical class 0.000 claims description 2
• ZFFYPGZDXUPKNK-UHFFFAOYSA-N 2,3-dihydro-1h-pyrrolo[2,3-b]pyridine Chemical compound C1=CN=C2NCCC2=C1 ZFFYPGZDXUPKNK-UHFFFAOYSA-N 0.000 claims description 2
• JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical class C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 claims description 2
• AOPRXJXHLWYPQR-UHFFFAOYSA-N 2-phenoxyacetamide Chemical compound NC(=O)COC1=CC=CC=C1 AOPRXJXHLWYPQR-UHFFFAOYSA-N 0.000 claims description 2
• KBRJQEVSKVOLNR-UHFFFAOYSA-N 2-phenylsulfanylacetamide Chemical compound NC(=O)CSC1=CC=CC=C1 KBRJQEVSKVOLNR-UHFFFAOYSA-N 0.000 claims description 2
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 2
• 241000237858 Gastropoda Species 0.000 claims description 2
• 229910019142 PO4 Inorganic materials 0.000 claims description 2
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• 125000000304 alkynyl group Chemical group 0.000 claims description 2
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• 125000005110 aryl thio group Chemical group 0.000 claims description 2
• 125000004104 aryloxy group Chemical group 0.000 claims description 2
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• RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 2
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
• 150000007942 carboxylates Chemical class 0.000 claims description 2
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 2
• 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
• 231100000024 genotoxic Toxicity 0.000 claims description 2
• 230000001738 genotoxic effect Effects 0.000 claims description 2
• DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Chemical class C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 2
• 230000007062 hydrolysis Effects 0.000 claims description 2
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• 208000026278 immune system disease Diseases 0.000 claims description 2
• GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 claims description 2
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• 125000001624 naphthyl group Chemical group 0.000 claims description 2
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• 125000003107 substituted aryl group Chemical group 0.000 claims description 2
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• WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical class C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims 1
• BNGITRCRSAWPSZ-UHFFFAOYSA-N 1h-pyrrolo[2,3-b]pyridine Chemical compound C1=CN=C2N[C]=CC2=C1 BNGITRCRSAWPSZ-UHFFFAOYSA-N 0.000 claims 1
• UZOFELREXGAFOI-UHFFFAOYSA-N 4-methylpiperidine Chemical compound CC1CCNCC1 UZOFELREXGAFOI-UHFFFAOYSA-N 0.000 claims 1
• 208000008720 Bone Marrow Neoplasms Diseases 0.000 claims 1
• YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 claims 1
• 150000001335 aliphatic alkanes Chemical group 0.000 claims 1
• 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
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• 125000000524 functional group Chemical group 0.000 claims 1
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• XSDLDLIXLLMXDY-UHFFFAOYSA-N n-methoxyhydroxylamine Chemical compound CONO XSDLDLIXLLMXDY-UHFFFAOYSA-N 0.000 claims 1
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• 238000004452 microanalysis Methods 0.000 description 117
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• KEORWPQKMNJCDM-YTTGMZPUSA-N 1-[2-[(3s)-3-[(dimethylamino)methyl]-3,4-dihydro-1h-isoquinoline-2-carbonyl]phenyl]-n-(4-hydroxyphenyl)-5-methyl-n-phenylpyrrole-3-carboxamide Chemical compound C([C@H]1CN(C)C)C2=CC=CC=C2CN1C(=O)C1=CC=CC=C1N(C(=C1)C)C=C1C(=O)N(C=1C=CC(O)=CC=1)C1=CC=CC=C1 KEORWPQKMNJCDM-YTTGMZPUSA-N 0.000 description 1
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• URFMEHHIOISODK-XIFFEERXSA-N 1-[3-chloro-4-hydroxy-5-methoxy-2-[(3S)-3-[(4-methylpiperazin-1-yl)methyl]-3,4-dihydro-1H-isoquinoline-2-carbonyl]phenyl]-N-(4-hydroxyphenyl)-N-phenylindole-3-carboxamide Chemical compound ClC=1C(=C(C=C(C=1O)OC)N1C=C(C2=CC=CC=C12)C(=O)N(C1=CC=CC=C1)C1=CC=C(C=C1)O)C(=O)N1CC2=CC=CC=C2C[C@H]1CN1CCN(CC1)C URFMEHHIOISODK-XIFFEERXSA-N 0.000 description 1
• WMXMHWOVDNKJKP-XIFFEERXSA-N 1-[4,5-dibromo-2-[(3s)-3-[(4-methylpiperazin-1-yl)methyl]-3,4-dihydro-1h-isoquinoline-2-carbonyl]phenyl]-n-(4-hydroxyphenyl)-5-methyl-n-phenylpyrrole-3-carboxamide Chemical class C1CN(C)CCN1C[C@H]1N(C(=O)C=2C(=CC(Br)=C(Br)C=2)N2C(=CC(=C2)C(=O)N(C=2C=CC=CC=2)C=2C=CC(O)=CC=2)C)CC2=CC=CC=C2C1 WMXMHWOVDNKJKP-XIFFEERXSA-N 0.000 description 1
• VYADYXZMLCZDAD-XIFFEERXSA-N 1-[4,5-difluoro-2-[(3s)-3-[(4-methylpiperazin-1-yl)methyl]-3,4-dihydro-1h-isoquinoline-2-carbonyl]phenyl]-n-(4-hydroxyphenyl)-5-methyl-n-phenylpyrrole-3-carboxamide Chemical class C1CN(C)CCN1C[C@H]1N(C(=O)C=2C(=CC(F)=C(F)C=2)N2C(=CC(=C2)C(=O)N(C=2C=CC=CC=2)C=2C=CC(O)=CC=2)C)CC2=CC=CC=C2C1 VYADYXZMLCZDAD-XIFFEERXSA-N 0.000 description 1
• SEJBBVPZSPSYIF-XIFFEERXSA-N 1-[4,5-dihydroxy-2-[(3S)-3-[(4-methylpiperazin-1-yl)methyl]-3,4-dihydro-1H-isoquinoline-2-carbonyl]phenyl]-N-(4-hydroxyphenyl)-N-phenylindole-3-carboxamide Chemical compound OC1=CC(=C(C=C1O)N1C=C(C2=CC=CC=C12)C(=O)N(C1=CC=CC=C1)C1=CC=C(C=C1)O)C(=O)N1CC2=CC=CC=C2C[C@H]1CN1CCN(CC1)C SEJBBVPZSPSYIF-XIFFEERXSA-N 0.000 description 1
• BUAIKMVWFBKFGE-DHUJRADRSA-N 1-[4,5-dimethoxy-2-[(3S)-3-[(4-methylpiperazin-1-yl)methyl]-3,4-dihydro-1H-isoquinoline-2-carbonyl]phenyl]-N-(4-hydroxyphenyl)-N-phenylindole-3-carboxamide Chemical compound COC1=CC(=C(C=C1OC)N1C=C(C2=CC=CC=C12)C(=O)N(C1=CC=CC=C1)C1=CC=C(C=C1)O)C(=O)N1CC2=CC=CC=C2C[C@H]1CN1CCN(CC1)C BUAIKMVWFBKFGE-DHUJRADRSA-N 0.000 description 1
• KEBFJGAJQIRMEV-DHUJRADRSA-N 1-[4-bromo-2-[(3s)-3-[(4-methylpiperazin-1-yl)methyl]-3,4-dihydro-1h-isoquinoline-2-carbonyl]phenyl]-n-(4-hydroxyphenyl)-5-methyl-n-phenylpyrrole-3-carboxamide Chemical class C1CN(C)CCN1C[C@H]1N(C(=O)C=2C(=CC=C(Br)C=2)N2C(=CC(=C2)C(=O)N(C=2C=CC=CC=2)C=2C=CC(O)=CC=2)C)CC2=CC=CC=C2C1 KEBFJGAJQIRMEV-DHUJRADRSA-N 0.000 description 1
• JQWCJIDFIOYPAD-DHUJRADRSA-N 1-[4-chloro-2-[(3S)-3-[(4-methylpiperazin-1-yl)methyl]-3,4-dihydro-1H-isoquinoline-2-carbonyl]phenyl]-N-(4-hydroxyphenyl)-5-methyl-N-phenylpyrrole-3-carboxamide Chemical class ClC1=CC(=C(C=C1)N1C=C(C=C1C)C(=O)N(C1=CC=CC=C1)C1=CC=C(C=C1)O)C(=O)N1CC2=CC=CC=C2C[C@H]1CN1CCN(CC1)C JQWCJIDFIOYPAD-DHUJRADRSA-N 0.000 description 1
• OUMASSHBKBETQQ-GXUZKUJRSA-N 1-[4-hydroxy-5-methoxy-2-[(3S)-3-(piperidin-1-ylmethyl)-3,4-dihydro-1H-isoquinoline-2-carbonyl]phenyl]-N-(4-hydroxyphenyl)-N-phenylindole-3-carboxamide hydrochloride Chemical compound Cl.COc1cc(c(cc1O)C(=O)N1Cc2ccccc2C[C@H]1CN1CCCCC1)-n1cc(C(=O)N(c2ccccc2)c2ccc(O)cc2)c2ccccc12 OUMASSHBKBETQQ-GXUZKUJRSA-N 0.000 description 1
• XTDQACDZTHCWLA-DHUJRADRSA-N 1-[4-hydroxy-5-methoxy-2-[(3S)-3-[(4-methylpiperazin-1-yl)methyl]-3,4-dihydro-1H-isoquinoline-2-carbonyl]phenyl]-N,N-diphenylindole-3-carboxamide Chemical compound COc1cc(c(cc1O)C(=O)N1Cc2ccccc2C[C@H]1CN1CCN(C)CC1)-n1cc(C(=O)N(c2ccccc2)c2ccccc2)c2ccccc12 XTDQACDZTHCWLA-DHUJRADRSA-N 0.000 description 1
• ZGGILLIHHSLVEW-BHVANESWSA-N 1-[4-hydroxy-5-methoxy-2-[(3S)-3-[(4-methylpiperazin-1-yl)methyl]-3,4-dihydro-1H-isoquinoline-2-carbonyl]phenyl]-N-(4-methylphenyl)-N-phenylindole-3-carboxamide Chemical compound OC1=CC(=C(C=C1OC)N1C=C(C2=CC=CC=C12)C(=O)N(C1=CC=CC=C1)C1=CC=C(C=C1)C)C(=O)N1CC2=CC=CC=C2C[C@H]1CN1CCN(CC1)C ZGGILLIHHSLVEW-BHVANESWSA-N 0.000 description 1
• GUTLWLPHRGSJCV-KDXMTYKHSA-N 1-[5-bromo-2-[(3S)-3-(4-methylpiperazine-1-carbonyl)-3,4-dihydro-1H-isoquinoline-2-carbonyl]phenyl]-N-(4-hydroxyphenyl)-N-(1H-indol-5-yl)-5-methylpyrrole-3-carboxamide Chemical class BrC=1C=CC(=C(C=1)N1C=C(C=C1C)C(=O)N(C=1C=C2C=CNC2=CC=1)C1=CC=C(C=C1)O)C(=O)N1CC2=CC=CC=C2C[C@H]1C(=O)N1CCN(CC1)C GUTLWLPHRGSJCV-KDXMTYKHSA-N 0.000 description 1
• QUIGPPILAWTSCN-UMSFTDKQSA-N 1-[5-bromo-2-[(3S)-3-(morpholin-4-ylmethyl)-3,4-dihydro-1H-isoquinoline-2-carbonyl]phenyl]-N-(4-hydroxyphenyl)-5-methyl-N-phenylpyrrole-3-carboxamide Chemical class BrC=1C=CC(=C(C=1)N1C=C(C=C1C)C(=O)N(C1=CC=CC=C1)C1=CC=C(C=C1)O)C(=O)N1CC2=CC=CC=C2C[C@H]1CN1CCOCC1 QUIGPPILAWTSCN-UMSFTDKQSA-N 0.000 description 1
• VJKSFULUWKOUGW-DHUJRADRSA-N 1-[5-bromo-2-[(3S)-3-(pyrrolidin-1-ylmethyl)-3,4-dihydro-1H-isoquinoline-2-carbonyl]phenyl]-N-(4-hydroxyphenyl)-N-(1H-indol-5-yl)-5-methylpyrrole-3-carboxamide Chemical class BrC=1C=CC(=C(C=1)N1C=C(C=C1C)C(=O)N(C=1C=C2C=CNC2=CC=1)C1=CC=C(C=C1)O)C(=O)N1CC2=CC=CC=C2C[C@H]1CN1CCCC1 VJKSFULUWKOUGW-DHUJRADRSA-N 0.000 description 1
• VDKILFIIPIODFF-UMSFTDKQSA-N 1-[5-bromo-2-[(3S)-3-[(4-methylpiperazin-1-yl)methyl]-3,4-dihydro-1H-isoquinoline-2-carbonyl]phenyl]-N,N-bis(4-hydroxyphenyl)-5-methylpyrrole-3-carboxamide Chemical compound BrC=1C=CC(=C(C=1)N1C=C(C=C1C)C(=O)N(C1=CC=C(C=C1)O)C1=CC=C(C=C1)O)C(=O)N1CC2=CC=CC=C2C[C@H]1CN1CCN(CC1)C VDKILFIIPIODFF-UMSFTDKQSA-N 0.000 description 1
• AVHYUXOBTDEJGF-UMSFTDKQSA-N 1-[5-bromo-2-[(3S)-3-[(4-methylpiperazin-1-yl)methyl]-3,4-dihydro-1H-isoquinoline-2-carbonyl]phenyl]-N,N-bis(4-hydroxyphenyl)indole-3-carboxamide Chemical compound BrC=1C=CC(=C(C=1)N1C=C(C2=CC=CC=C12)C(=O)N(C1=CC=C(C=C1)O)C1=CC=C(C=C1)O)C(=O)N1CC2=CC=CC=C2C[C@H]1CN1CCN(CC1)C AVHYUXOBTDEJGF-UMSFTDKQSA-N 0.000 description 1
• VUEKGWMVAAFZJW-DHUJRADRSA-N 1-[5-bromo-2-[(3S)-3-[(4-methylpiperazin-1-yl)methyl]-3,4-dihydro-1H-isoquinoline-2-carbonyl]phenyl]-N-(4-chlorophenyl)-N-(4-hydroxyphenyl)-5-methylpyrrole-3-carboxamide Chemical class BrC=1C=CC(=C(C=1)N1C=C(C=C1C)C(=O)N(C1=CC=C(C=C1)O)C1=CC=C(C=C1)Cl)C(=O)N1CC2=CC=CC=C2C[C@H]1CN1CCN(CC1)C VUEKGWMVAAFZJW-DHUJRADRSA-N 0.000 description 1
• GHCWSVWHLWZQOW-DHUJRADRSA-N 1-[5-bromo-2-[(3S)-3-[(4-methylpiperazin-1-yl)methyl]-3,4-dihydro-1H-isoquinoline-2-carbonyl]phenyl]-N-(4-chlorophenyl)-N-(4-hydroxyphenyl)indole-3-carboxamide Chemical class BrC=1C=CC(=C(C=1)N1C=C(C2=CC=CC=C12)C(=O)N(C1=CC=C(C=C1)O)C1=CC=C(C=C1)Cl)C(=O)N1CC2=CC=CC=C2C[C@H]1CN1CCN(CC1)C GHCWSVWHLWZQOW-DHUJRADRSA-N 0.000 description 1
• BRDUAXDBHUEFLV-DHUJRADRSA-N 1-[5-bromo-2-[(3S)-3-[(4-methylpiperazin-1-yl)methyl]-3,4-dihydro-1H-isoquinoline-2-carbonyl]phenyl]-N-(4-fluorophenyl)-N-(4-hydroxyphenyl)-5-methylpyrrole-3-carboxamide Chemical class BrC=1C=CC(=C(C=1)N1C=C(C=C1C)C(=O)N(C1=CC=C(C=C1)O)C1=CC=C(C=C1)F)C(=O)N1CC2=CC=CC=C2C[C@H]1CN1CCN(CC1)C BRDUAXDBHUEFLV-DHUJRADRSA-N 0.000 description 1
• AJCQUXBFGOPVCK-DHUJRADRSA-N 1-[5-bromo-2-[(3S)-3-[(4-methylpiperazin-1-yl)methyl]-3,4-dihydro-1H-isoquinoline-2-carbonyl]phenyl]-N-(4-fluorophenyl)-N-(4-hydroxyphenyl)indole-3-carboxamide Chemical class BrC=1C=CC(=C(C=1)N1C=C(C2=CC=CC=C12)C(=O)N(C1=CC=C(C=C1)O)C1=CC=C(C=C1)F)C(=O)N1CC2=CC=CC=C2C[C@H]1CN1CCN(CC1)C AJCQUXBFGOPVCK-DHUJRADRSA-N 0.000 description 1
• UFVUCTMQBNUYSY-BHVANESWSA-N 1-[5-bromo-2-[(3S)-3-[(4-methylpiperazin-1-yl)methyl]-3,4-dihydro-1H-isoquinoline-2-carbonyl]phenyl]-N-(4-hydroxyphenyl)-5-methyl-N-(4-methylphenyl)pyrrole-3-carboxamide Chemical class BrC=1C=CC(=C(C=1)N1C=C(C=C1C)C(=O)N(C1=CC=C(C=C1)C)C1=CC=C(C=C1)O)C(=O)N1CC2=CC=CC=C2C[C@H]1CN1CCN(CC1)C UFVUCTMQBNUYSY-BHVANESWSA-N 0.000 description 1
• ZENQTJZWWXXSPO-DHUJRADRSA-N 1-[5-bromo-2-[(3S)-3-[(4-methylpiperazin-1-yl)methyl]-3,4-dihydro-1H-isoquinoline-2-carbonyl]phenyl]-N-(4-hydroxyphenyl)-5-methyl-N-phenylpyrrole-3-carboxamide Chemical class BrC=1C=CC(=C(C=1)N1C=C(C=C1C)C(=O)N(C1=CC=CC=C1)C1=CC=C(C=C1)O)C(=O)N1CC2=CC=CC=C2C[C@H]1CN1CCN(CC1)C ZENQTJZWWXXSPO-DHUJRADRSA-N 0.000 description 1
• QAEVQMLWGFXVQV-BHVANESWSA-N 1-[5-bromo-2-[(3S)-3-[(4-methylpiperazin-1-yl)methyl]-3,4-dihydro-1H-isoquinoline-2-carbonyl]phenyl]-N-(4-hydroxyphenyl)-N-(4-methylphenyl)indole-3-carboxamide Chemical class BrC=1C=CC(=C(C=1)N1C=C(C2=CC=CC=C12)C(=O)N(C1=CC=C(C=C1)C)C1=CC=C(C=C1)O)C(=O)N1CC2=CC=CC=C2C[C@H]1CN1CCN(CC1)C QAEVQMLWGFXVQV-BHVANESWSA-N 0.000 description 1
• YUPKOCPODSOACE-UMSFTDKQSA-N 1-[5-chloro-2-[(3S)-3-[(4-methylpiperazin-1-yl)methyl]-3,4-dihydro-1H-isoquinoline-2-carbonyl]phenyl]-N,N-bis(4-hydroxyphenyl)-5-methylpyrrole-3-carboxamide Chemical compound ClC=1C=CC(=C(C=1)N1C=C(C=C1C)C(=O)N(C1=CC=C(C=C1)O)C1=CC=C(C=C1)O)C(=O)N1CC2=CC=CC=C2C[C@H]1CN1CCN(CC1)C YUPKOCPODSOACE-UMSFTDKQSA-N 0.000 description 1
• UDEKRVLUJGIDPV-UMSFTDKQSA-N 1-[5-chloro-2-[(3S)-3-[(4-methylpiperazin-1-yl)methyl]-3,4-dihydro-1H-isoquinoline-2-carbonyl]phenyl]-N,N-bis(4-hydroxyphenyl)indole-3-carboxamide Chemical compound ClC=1C=CC(=C(C=1)N1C=C(C2=CC=CC=C12)C(=O)N(C1=CC=C(C=C1)O)C1=CC=C(C=C1)O)C(=O)N1CC2=CC=CC=C2C[C@H]1CN1CCN(CC1)C UDEKRVLUJGIDPV-UMSFTDKQSA-N 0.000 description 1
• GVRBFGJJEYIFFN-BHVANESWSA-N 1-[5-chloro-2-[(3S)-3-[(4-methylpiperazin-1-yl)methyl]-3,4-dihydro-1H-isoquinoline-2-carbonyl]phenyl]-N,N-diphenylindole-3-carboxamide Chemical compound ClC=1C=CC(=C(C=1)N1C=C(C2=CC=CC=C12)C(=O)N(C1=CC=CC=C1)C1=CC=CC=C1)C(=O)N1CC2=CC=CC=C2C[C@H]1CN1CCN(CC1)C GVRBFGJJEYIFFN-BHVANESWSA-N 0.000 description 1
• MIGOTVBALYEVNJ-DHUJRADRSA-N 1-[5-chloro-2-[(3S)-3-[(4-methylpiperazin-1-yl)methyl]-3,4-dihydro-1H-isoquinoline-2-carbonyl]phenyl]-N-(4-chlorophenyl)-N-(4-hydroxyphenyl)indole-3-carboxamide Chemical class ClC=1C=CC(=C(C=1)N1C=C(C2=CC=CC=C12)C(=O)N(C1=CC=C(C=C1)O)C1=CC=C(C=C1)Cl)C(=O)N1CC2=CC=CC=C2C[C@H]1CN1CCN(CC1)C MIGOTVBALYEVNJ-DHUJRADRSA-N 0.000 description 1
• SQKWTNKFCWTIPM-DHUJRADRSA-N 1-[5-chloro-2-[(3S)-3-[(4-methylpiperazin-1-yl)methyl]-3,4-dihydro-1H-isoquinoline-2-carbonyl]phenyl]-N-(4-fluorophenyl)-N-(4-hydroxyphenyl)-5-methylpyrrole-3-carboxamide Chemical class ClC=1C=CC(=C(C=1)N1C=C(C=C1C)C(=O)N(C1=CC=C(C=C1)O)C1=CC=C(C=C1)F)C(=O)N1CC2=CC=CC=C2C[C@H]1CN1CCN(CC1)C SQKWTNKFCWTIPM-DHUJRADRSA-N 0.000 description 1
• VVFOGWWGOKDKQG-DHUJRADRSA-N 1-[5-chloro-2-[(3S)-3-[(4-methylpiperazin-1-yl)methyl]-3,4-dihydro-1H-isoquinoline-2-carbonyl]phenyl]-N-(4-fluorophenyl)-N-(4-hydroxyphenyl)indole-3-carboxamide Chemical class ClC=1C=CC(=C(C=1)N1C=C(C2=CC=CC=C12)C(=O)N(C1=CC=C(C=C1)O)C1=CC=C(C=C1)F)C(=O)N1CC2=CC=CC=C2C[C@H]1CN1CCN(CC1)C VVFOGWWGOKDKQG-DHUJRADRSA-N 0.000 description 1
• FZBCNHCQYOQTSW-BHVANESWSA-N 1-[5-chloro-2-[(3S)-3-[(4-methylpiperazin-1-yl)methyl]-3,4-dihydro-1H-isoquinoline-2-carbonyl]phenyl]-N-(4-hydroxyphenyl)-5-methyl-N-(4-methylphenyl)pyrrole-3-carboxamide Chemical class ClC=1C=CC(=C(C=1)N1C=C(C=C1C)C(=O)N(C1=CC=C(C=C1)C)C1=CC=C(C=C1)O)C(=O)N1CC2=CC=CC=C2C[C@H]1CN1CCN(CC1)C FZBCNHCQYOQTSW-BHVANESWSA-N 0.000 description 1
• TWBGSNMKLYGPLP-DHUJRADRSA-N 1-[5-chloro-2-[(3S)-3-[(4-methylpiperazin-1-yl)methyl]-3,4-dihydro-1H-isoquinoline-2-carbonyl]phenyl]-N-(4-hydroxyphenyl)-5-methyl-N-phenylpyrrole-3-carboxamide Chemical class ClC=1C=CC(=C(C=1)N1C=C(C=C1C)C(=O)N(C1=CC=CC=C1)C1=CC=C(C=C1)O)C(=O)N1CC2=CC=CC=C2C[C@H]1CN1CCN(CC1)C TWBGSNMKLYGPLP-DHUJRADRSA-N 0.000 description 1
• WCMBIYUZNBUEHV-BHVANESWSA-N 1-[5-chloro-2-[(3S)-3-[(4-methylpiperazin-1-yl)methyl]-3,4-dihydro-1H-isoquinoline-2-carbonyl]phenyl]-N-(4-hydroxyphenyl)-N-(1H-indol-5-yl)-5-methylpyrrole-3-carboxamide Chemical class ClC=1C=CC(=C(C=1)N1C=C(C=C1C)C(=O)N(C=1C=C2C=CNC2=CC=1)C1=CC=C(C=C1)O)C(=O)N1CC2=CC=CC=C2C[C@H]1CN1CCN(CC1)C WCMBIYUZNBUEHV-BHVANESWSA-N 0.000 description 1
• XIKMCVAWPIFRMS-BHVANESWSA-N 1-[5-chloro-2-[(3S)-3-[(4-methylpiperazin-1-yl)methyl]-3,4-dihydro-1H-isoquinoline-2-carbonyl]phenyl]-N-(4-hydroxyphenyl)-N-(1H-indol-5-yl)indole-3-carboxamide Chemical class ClC=1C=CC(=C(C=1)N1C=C(C2=CC=CC=C12)C(=O)N(C=1C=C2C=CNC2=CC=1)C1=CC=C(C=C1)O)C(=O)N1CC2=CC=CC=C2C[C@H]1CN1CCN(CC1)C XIKMCVAWPIFRMS-BHVANESWSA-N 0.000 description 1
• UDFWTOKGCDMUDT-BHVANESWSA-N 1-[5-chloro-2-[(3S)-3-[(4-methylpiperazin-1-yl)methyl]-3,4-dihydro-1H-isoquinoline-2-carbonyl]phenyl]-N-(4-hydroxyphenyl)-N-(4-methylphenyl)indole-3-carboxamide Chemical class ClC=1C=CC(=C(C=1)N1C=C(C2=CC=CC=C12)C(=O)N(C1=CC=C(C=C1)C)C1=CC=C(C=C1)O)C(=O)N1CC2=CC=CC=C2C[C@H]1CN1CCN(CC1)C UDFWTOKGCDMUDT-BHVANESWSA-N 0.000 description 1
• ZWLWAAQLTGWOBQ-WBCKFURZSA-N 1-[5-chloro-2-[(3S)-3-[(4-methylpiperazin-1-yl)methyl]-3,4-dihydro-1H-isoquinoline-2-carbonyl]phenyl]-N-phenyl-N-(4-phenylmethoxyphenyl)indole-3-carboxamide Chemical compound C(C1=CC=CC=C1)OC1=CC=C(C=C1)N(C(=O)C1=CN(C2=CC=CC=C12)C1=C(C=CC(=C1)Cl)C(=O)N1CC2=CC=CC=C2C[C@H]1CN1CCN(CC1)C)C1=CC=CC=C1 ZWLWAAQLTGWOBQ-WBCKFURZSA-N 0.000 description 1
• MPQWNASAMQDXIE-YTTGMZPUSA-N 1-[5-chloro-2-[(3S)-3-[(dimethylamino)methyl]-3,4-dihydro-1H-isoquinoline-2-carbonyl]phenyl]-N-(4-hydroxyphenyl)-5-methyl-N-phenylpyrrole-3-carboxamide Chemical class ClC=1C=CC(=C(C=1)N1C=C(C=C1C)C(=O)N(C1=CC=CC=C1)C1=CC=C(C=C1)O)C(=O)N1CC2=CC=CC=C2C[C@H]1CN(C)C MPQWNASAMQDXIE-YTTGMZPUSA-N 0.000 description 1
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