JP2004518669A - ４−アリール置換インドリノン - Google Patents

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Publication number

JP2004518669A

JP2004518669A JP2002556186A JP2002556186A JP2004518669A JP 2004518669 A JP2004518669 A JP 2004518669A JP 2002556186 A JP2002556186 A JP 2002556186A JP 2002556186 A JP2002556186 A JP 2002556186A JP 2004518669 A JP2004518669 A JP 2004518669A

Authority

JP

Japan

Prior art keywords

phenyl

dihydro

methyl

dimethyl

indole

Prior art date

2000-12-20

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.)

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• JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical class C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 title description 15
• 102000001253 Protein Kinase Human genes 0.000 claims abstract description 96
• 108060006633 protein kinase Proteins 0.000 claims abstract description 96
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 89
• 201000010099 disease Diseases 0.000 claims abstract description 84
• 238000000034 method Methods 0.000 claims abstract description 65
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 24
• 125000003118 aryl group Chemical group 0.000 claims description 200
• 150000001875 compounds Chemical class 0.000 claims description 165
• 125000000217 alkyl group Chemical group 0.000 claims description 112
• 125000000623 heterocyclic group Chemical group 0.000 claims description 78
• 229910052757 nitrogen Inorganic materials 0.000 claims description 78
• -1 —COR 12 Chemical group 0.000 claims description 70
• 125000003342 alkenyl group Chemical group 0.000 claims description 65
• 125000000304 alkynyl group Chemical group 0.000 claims description 63
• 206010028980 Neoplasm Diseases 0.000 claims description 53
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 48
• 108010053099 Vascular Endothelial Growth Factor Receptor-2 Proteins 0.000 claims description 47
• 150000003839 salts Chemical class 0.000 claims description 47
• 229910052739 hydrogen Inorganic materials 0.000 claims description 45
• 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 44
• 239000001257 hydrogen Substances 0.000 claims description 43
• 102000027426 receptor tyrosine kinases Human genes 0.000 claims description 43
• 108091008598 receptor tyrosine kinases Proteins 0.000 claims description 43
• 229910052736 halogen Inorganic materials 0.000 claims description 39
• 150000002367 halogens Chemical class 0.000 claims description 39
• 230000003197 catalytic effect Effects 0.000 claims description 38
• 102000009516 Protein Serine-Threonine Kinases Human genes 0.000 claims description 36
• 108010009341 Protein Serine-Threonine Kinases Proteins 0.000 claims description 36
• 201000011510 cancer Diseases 0.000 claims description 32
• 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims description 31
• 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims description 31
• 102100033177 Vascular endothelial growth factor receptor 2 Human genes 0.000 claims description 30
• 230000033115 angiogenesis Effects 0.000 claims description 30
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 24
• 239000003814 drug Substances 0.000 claims description 20
• 229910052760 oxygen Inorganic materials 0.000 claims description 18
• 125000005842 heteroatom Chemical group 0.000 claims description 16
• 150000002431 hydrogen Chemical class 0.000 claims description 16
• 229910052717 sulfur Inorganic materials 0.000 claims description 16
• 102100030086 Receptor tyrosine-protein kinase erbB-2 Human genes 0.000 claims description 14
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 14
• 230000001105 regulatory effect Effects 0.000 claims description 13
• 125000005843 halogen group Chemical group 0.000 claims description 12
• 125000001424 substituent group Chemical group 0.000 claims description 12
• 108091000080 Phosphotransferase Proteins 0.000 claims description 10
• 102000016549 Vascular Endothelial Growth Factor Receptor-2 Human genes 0.000 claims description 10
• 230000001413 cellular effect Effects 0.000 claims description 10
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• 208000026310 Breast neoplasm Diseases 0.000 claims description 9
• 206010016654 Fibrosis Diseases 0.000 claims description 9
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 9
• 101001012157 Homo sapiens Receptor tyrosine-protein kinase erbB-2 Proteins 0.000 claims description 8
• 201000004681 Psoriasis Diseases 0.000 claims description 8
• 239000002246 antineoplastic agent Substances 0.000 claims description 8
• 239000000460 chlorine Chemical group 0.000 claims description 8
• 229940127089 cytotoxic agent Drugs 0.000 claims description 8
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 7
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
• 102100039137 Insulin receptor-related protein Human genes 0.000 claims description 7
• 206010061535 Ovarian neoplasm Diseases 0.000 claims description 7
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
• 229910052794 bromium Inorganic materials 0.000 claims description 7
• 229910052801 chlorine Inorganic materials 0.000 claims description 7
• 239000011737 fluorine Substances 0.000 claims description 7
• 229910052731 fluorine Inorganic materials 0.000 claims description 7
• 239000011630 iodine Chemical group 0.000 claims description 7
• 229910052740 iodine Chemical group 0.000 claims description 7
• 208000020816 lung neoplasm Diseases 0.000 claims description 7
• UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 claims description 7
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 6
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• 125000001153 fluoro group Chemical group F* 0.000 claims description 6
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• 102000001393 Platelet-Derived Growth Factor alpha Receptor Human genes 0.000 claims description 5
• 108010068588 Platelet-Derived Growth Factor alpha Receptor Proteins 0.000 claims description 5
• 101710098940 Pro-epidermal growth factor Proteins 0.000 claims description 5
• 101710100969 Receptor tyrosine-protein kinase erbB-3 Proteins 0.000 claims description 5
• 102100029986 Receptor tyrosine-protein kinase erbB-3 Human genes 0.000 claims description 5
• 102100029981 Receptor tyrosine-protein kinase erbB-4 Human genes 0.000 claims description 5
• 101710100963 Receptor tyrosine-protein kinase erbB-4 Proteins 0.000 claims description 5
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• 101100381481 Caenorhabditis elegans baz-2 gene Proteins 0.000 claims description 4
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• 108010024986 Cyclin-Dependent Kinase 2 Proteins 0.000 claims description 4
• 102100036239 Cyclin-dependent kinase 2 Human genes 0.000 claims description 4
• 208000032612 Glial tumor Diseases 0.000 claims description 4
• 206010018338 Glioma Diseases 0.000 claims description 4
• 208000007766 Kaposi sarcoma Diseases 0.000 claims description 4
• 102100027754 Mast/stem cell growth factor receptor Kit Human genes 0.000 claims description 4
• 230000004761 fibrosis Effects 0.000 claims description 4
• 208000005017 glioblastoma Diseases 0.000 claims description 4
• 230000003463 hyperproliferative effect Effects 0.000 claims description 4
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
• 229940124597 therapeutic agent Drugs 0.000 claims description 4
• CHEYEJGXQSHSFE-UHFFFAOYSA-N 2-(triazol-1-yl)ethanamine Chemical compound NCCN1C=CN=N1 CHEYEJGXQSHSFE-UHFFFAOYSA-N 0.000 claims description 3
• WRXNJTBODVGDRY-UHFFFAOYSA-N 2-pyrrolidin-1-ylethanamine Chemical compound NCCN1CCCC1 WRXNJTBODVGDRY-UHFFFAOYSA-N 0.000 claims description 3
• 206010003571 Astrocytoma Diseases 0.000 claims description 3
• 101000896657 Homo sapiens Mitotic checkpoint serine/threonine-protein kinase BUB1 Proteins 0.000 claims description 3
• 101000818543 Homo sapiens Tyrosine-protein kinase ZAP-70 Proteins 0.000 claims description 3
• 102100021691 Mitotic checkpoint serine/threonine-protein kinase BUB1 Human genes 0.000 claims description 3
• 206010060862 Prostate cancer Diseases 0.000 claims description 3
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 3
• 102100021125 Tyrosine-protein kinase ZAP-70 Human genes 0.000 claims description 3
• 229940100198 alkylating agent Drugs 0.000 claims description 3
• 239000002168 alkylating agent Substances 0.000 claims description 3
• 201000010536 head and neck cancer Diseases 0.000 claims description 3
• 208000014829 head and neck neoplasm Diseases 0.000 claims description 3
• 208000027866 inflammatory disease Diseases 0.000 claims description 3
• 102000037979 non-receptor tyrosine kinases Human genes 0.000 claims description 3
• 108091008046 non-receptor tyrosine kinases Proteins 0.000 claims description 3
• 201000008482 osteoarthritis Diseases 0.000 claims description 3
• 208000006542 von Hippel-Lindau disease Diseases 0.000 claims description 3
• FPYJSJDOHRDAMT-KQWNVCNZSA-N 1h-indole-5-sulfonamide, n-(3-chlorophenyl)-3-[[3,5-dimethyl-4-[(4-methyl-1-piperazinyl)carbonyl]-1h-pyrrol-2-yl]methylene]-2,3-dihydro-n-methyl-2-oxo-, (3z)- Chemical compound C=1C=C2NC(=O)\C(=C/C3=C(C(C(=O)N4CCN(C)CC4)=C(C)N3)C)C2=CC=1S(=O)(=O)N(C)C1=CC=CC(Cl)=C1 FPYJSJDOHRDAMT-KQWNVCNZSA-N 0.000 claims description 2
• 101100498819 Caenorhabditis elegans ddr-1 gene Proteins 0.000 claims description 2
• 101100498823 Caenorhabditis elegans ddr-2 gene Proteins 0.000 claims description 2
• 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 2
• 101100540419 Danio rerio kdrl gene Proteins 0.000 claims description 2
• 108091008794 FGF receptors Proteins 0.000 claims description 2
• 101150118938 FLK gene Proteins 0.000 claims description 2
• 229930012538 Paclitaxel Natural products 0.000 claims description 2
• 101100173553 Rattus norvegicus Fer gene Proteins 0.000 claims description 2
• 230000000340 anti-metabolite Effects 0.000 claims description 2
• 229940100197 antimetabolite Drugs 0.000 claims description 2
• 239000002256 antimetabolite Substances 0.000 claims description 2
• 102000052178 fibroblast growth factor receptor activity proteins Human genes 0.000 claims description 2
• 229960001156 mitoxantrone Drugs 0.000 claims description 2
• KKZJGLLVHKMTCM-UHFFFAOYSA-N mitoxantrone Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO KKZJGLLVHKMTCM-UHFFFAOYSA-N 0.000 claims description 2
• 229930014626 natural product Natural products 0.000 claims description 2
• 229960001592 paclitaxel Drugs 0.000 claims description 2
• 206010041823 squamous cell carcinoma Diseases 0.000 claims description 2
• RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims description 2
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 2
• 229910005965 SO 2 Inorganic materials 0.000 claims 66
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 11
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 10
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 8
• OMBFUKZWGIHJDZ-IAGOWNOFSA-N 3-[[3-[(3R,5R)-3,5-dimethylpiperazine-1-carbonyl]-5-methyl-1H-pyrrol-2-yl]methylidene]-4-(3-fluorophenyl)-1H-indol-2-one Chemical compound C1[C@@H](C)N[C@H](C)CN1C(=O)C1=C(C=C2C3=C(C=CC=C3NC2=O)C=2C=C(F)C=CC=2)NC(C)=C1 OMBFUKZWGIHJDZ-IAGOWNOFSA-N 0.000 claims 3
• YNQYKQKNMVRPNW-IAGOWNOFSA-N 3-[[4-[(3R,5R)-3,5-dimethylpiperazine-1-carbonyl]-3,5-dimethyl-1H-pyrrol-2-yl]methylidene]-4-(3-methoxyphenyl)-1H-indol-2-one Chemical compound COC1=CC=CC(C=2C=3C(=CC4=C(C(C(=O)N5C[C@@H](C)N[C@H](C)C5)=C(C)N4)C)C(=O)NC=3C=CC=2)=C1 YNQYKQKNMVRPNW-IAGOWNOFSA-N 0.000 claims 3
• SLYDLEPXGOJXRI-IAGOWNOFSA-N 3-[[4-[(3R,5R)-3,5-dimethylpiperazine-1-carbonyl]-3,5-dimethyl-1H-pyrrol-2-yl]methylidene]-4-(4-methoxyphenyl)-1H-indol-2-one Chemical compound C1=CC(OC)=CC=C1C1=CC=CC(NC2=O)=C1C2=CC1=C(C)C(C(=O)N2C[C@@H](C)N[C@H](C)C2)=C(C)N1 SLYDLEPXGOJXRI-IAGOWNOFSA-N 0.000 claims 3
• CARQSIFVDPCMTO-IAGOWNOFSA-N 4-(4-chlorophenyl)-3-[[3-[(3R,5R)-3,5-dimethylpiperazine-1-carbonyl]-5-methyl-1H-pyrrol-2-yl]methylidene]-1H-indol-2-one Chemical compound C1[C@@H](C)N[C@H](C)CN1C(=O)C1=C(C=C2C3=C(C=CC=C3NC2=O)C=2C=CC(Cl)=CC=2)NC(C)=C1 CARQSIFVDPCMTO-IAGOWNOFSA-N 0.000 claims 3
• VRDZWSOXVUAKHZ-UHFFFAOYSA-N 2,4-dimethyl-5-[[2-oxo-4-[3-(trifluoromethyl)phenyl]-1h-indol-3-ylidene]methyl]-n-(2-pyrrolidin-1-ylethyl)-1h-pyrrole-3-carboxamide Chemical compound CC=1C(C(=O)NCCN2CCCC2)=C(C)NC=1C=C(C=12)C(=O)NC2=CC=CC=1C1=CC=CC(C(F)(F)F)=C1 VRDZWSOXVUAKHZ-UHFFFAOYSA-N 0.000 claims 2
• WQPBSCLIBHMJJX-UHFFFAOYSA-N 2,4-dimethyl-5-[[2-oxo-4-[3-(trifluoromethyl)phenyl]-1h-indol-3-ylidene]methyl]-n-[2-(triazol-1-yl)ethyl]-1h-pyrrole-3-carboxamide Chemical compound CC=1C(C(=O)NCCN2N=NC=C2)=C(C)NC=1C=C(C=12)C(=O)NC2=CC=CC=1C1=CC=CC(C(F)(F)F)=C1 WQPBSCLIBHMJJX-UHFFFAOYSA-N 0.000 claims 2
• AWQPLPDSGWJCFI-UHFFFAOYSA-N 2,4-dimethyl-5-[[2-oxo-4-[4-(trifluoromethoxy)phenyl]-1h-indol-3-ylidene]methyl]-n-[2-(triazol-1-yl)ethyl]-1h-pyrrole-3-carboxamide Chemical compound CC=1C(C(=O)NCCN2N=NC=C2)=C(C)NC=1C=C(C=12)C(=O)NC2=CC=CC=1C1=CC=C(OC(F)(F)F)C=C1 AWQPLPDSGWJCFI-UHFFFAOYSA-N 0.000 claims 2
• WWFONFNTBIRHHQ-UHFFFAOYSA-N 2-[[4-(2-fluorophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-5-methyl-n-(2-pyrrolidin-1-ylethyl)-1h-pyrrole-3-carboxamide Chemical compound O=C1NC2=CC=CC(C=3C(=CC=CC=3)F)=C2C1=CC=1NC(C)=CC=1C(=O)NCCN1CCCC1 WWFONFNTBIRHHQ-UHFFFAOYSA-N 0.000 claims 2
• MPYXQHOXIXPUIY-UHFFFAOYSA-N 2-[[4-(2-fluorophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-5-methyl-n-[2-(triazol-1-yl)ethyl]-1h-pyrrole-3-carboxamide Chemical compound O=C1NC2=CC=CC(C=3C(=CC=CC=3)F)=C2C1=CC=1NC(C)=CC=1C(=O)NCCN1C=CN=N1 MPYXQHOXIXPUIY-UHFFFAOYSA-N 0.000 claims 2
• LZWCQKJJTUNHNL-UHFFFAOYSA-N 2-[[4-(3-bromophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-5-methyl-n-(2-pyrrolidin-1-ylethyl)-1h-pyrrole-3-carboxamide Chemical compound O=C1NC2=CC=CC(C=3C=C(Br)C=CC=3)=C2C1=CC=1NC(C)=CC=1C(=O)NCCN1CCCC1 LZWCQKJJTUNHNL-UHFFFAOYSA-N 0.000 claims 2
• UXOTVNCSRBHACK-UHFFFAOYSA-N 2-[[4-(3-bromophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-5-methyl-n-[2-(triazol-1-yl)ethyl]-1h-pyrrole-3-carboxamide Chemical compound O=C1NC2=CC=CC(C=3C=C(Br)C=CC=3)=C2C1=CC=1NC(C)=CC=1C(=O)NCCN1C=CN=N1 UXOTVNCSRBHACK-UHFFFAOYSA-N 0.000 claims 2
• QFBVFXVKRWTEDQ-UHFFFAOYSA-N 2-[[4-(3-chlorophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-5-methyl-n-[2-(triazol-1-yl)ethyl]-1h-pyrrole-3-carboxamide Chemical compound O=C1NC2=CC=CC(C=3C=C(Cl)C=CC=3)=C2C1=CC=1NC(C)=CC=1C(=O)NCCN1C=CN=N1 QFBVFXVKRWTEDQ-UHFFFAOYSA-N 0.000 claims 2
• MBYSYJLDYCWYFM-UHFFFAOYSA-N 2-[[4-(3-methoxyphenyl)-2-oxo-1h-indol-3-ylidene]methyl]-5-methyl-n-(2-pyrrolidin-1-ylethyl)-1h-pyrrole-3-carboxamide Chemical compound COC1=CC=CC(C=2C=3C(=CC4=C(C=C(C)N4)C(=O)NCCN4CCCC4)C(=O)NC=3C=CC=2)=C1 MBYSYJLDYCWYFM-UHFFFAOYSA-N 0.000 claims 2
• XUJAOXLHJLEGIP-UHFFFAOYSA-N 2-[[4-(3-methoxyphenyl)-2-oxo-1h-indol-3-ylidene]methyl]-5-methyl-n-[2-(triazol-1-yl)ethyl]-1h-pyrrole-3-carboxamide Chemical compound COC1=CC=CC(C=2C=3C(=CC4=C(C=C(C)N4)C(=O)NCCN4N=NC=C4)C(=O)NC=3C=CC=2)=C1 XUJAOXLHJLEGIP-UHFFFAOYSA-N 0.000 claims 2
• ZBKZSYQZWMQECM-UHFFFAOYSA-N 2-[[4-(4-bromophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-5-methyl-n-(2-pyrrolidin-1-ylethyl)-1h-pyrrole-3-carboxamide Chemical compound O=C1NC2=CC=CC(C=3C=CC(Br)=CC=3)=C2C1=CC=1NC(C)=CC=1C(=O)NCCN1CCCC1 ZBKZSYQZWMQECM-UHFFFAOYSA-N 0.000 claims 2
• KNNIAMMFXFIEET-UHFFFAOYSA-N 2-[[4-(4-bromophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-5-methyl-n-[2-(triazol-1-yl)ethyl]-1h-pyrrole-3-carboxamide Chemical compound O=C1NC2=CC=CC(C=3C=CC(Br)=CC=3)=C2C1=CC=1NC(C)=CC=1C(=O)NCCN1C=CN=N1 KNNIAMMFXFIEET-UHFFFAOYSA-N 0.000 claims 2
• AMKILMQZHWJJCT-UHFFFAOYSA-N 2-[[4-(4-fluorophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-5-methyl-n-(3-pyrrolidin-1-ylpropyl)-1h-pyrrole-3-carboxamide Chemical compound O=C1NC2=CC=CC(C=3C=CC(F)=CC=3)=C2C1=CC=1NC(C)=CC=1C(=O)NCCCN1CCCC1 AMKILMQZHWJJCT-UHFFFAOYSA-N 0.000 claims 2
• KLPDZNJUFDCVSM-UHFFFAOYSA-N 2-[[4-(4-fluorophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-5-methyl-n-[2-(triazol-1-yl)ethyl]-1h-pyrrole-3-carboxamide Chemical compound O=C1NC2=CC=CC(C=3C=CC(F)=CC=3)=C2C1=CC=1NC(C)=CC=1C(=O)NCCN1C=CN=N1 KLPDZNJUFDCVSM-UHFFFAOYSA-N 0.000 claims 2
• IKXPGXCQWHTNQY-UHFFFAOYSA-N 2-[[4-(4-methoxyphenyl)-2-oxo-1h-indol-3-ylidene]methyl]-5-methyl-n-[2-(triazol-1-yl)ethyl]-1h-pyrrole-3-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=CC=CC(NC2=O)=C1C2=CC1=C(C(=O)NCCN2N=NC=C2)C=C(C)N1 IKXPGXCQWHTNQY-UHFFFAOYSA-N 0.000 claims 2
• VGNGCEOLEPSPNU-UHFFFAOYSA-N 3-[(3,5-dimethyl-1h-pyrrol-2-yl)methylidene]-4-(3-fluorophenyl)-1h-indol-2-one Chemical compound N1C(C)=CC(C)=C1C=C1C2=C(C=3C=C(F)C=CC=3)C=CC=C2NC1=O VGNGCEOLEPSPNU-UHFFFAOYSA-N 0.000 claims 2
• RCSCKFQMSMVNJE-UHFFFAOYSA-N 3-[(3,5-dimethyl-1h-pyrrol-2-yl)methylidene]-4-(3-methoxyphenyl)-1h-indol-2-one Chemical compound COC1=CC=CC(C=2C=3C(=CC4=C(C=C(C)N4)C)C(=O)NC=3C=CC=2)=C1 RCSCKFQMSMVNJE-UHFFFAOYSA-N 0.000 claims 2
• BHDNPWIGOZQIDE-UHFFFAOYSA-N 3-[(3,5-dimethyl-1h-pyrrol-2-yl)methylidene]-4-(4-fluorophenyl)-1h-indol-2-one Chemical compound N1C(C)=CC(C)=C1C=C1C2=C(C=3C=CC(F)=CC=3)C=CC=C2NC1=O BHDNPWIGOZQIDE-UHFFFAOYSA-N 0.000 claims 2
• CMOLXROSUKSQJU-UHFFFAOYSA-N 3-[(3,5-dimethyl-1h-pyrrol-2-yl)methylidene]-4-(4-methoxyphenyl)-1h-indol-2-one Chemical compound C1=CC(OC)=CC=C1C1=CC=CC(NC2=O)=C1C2=CC1=C(C)C=C(C)N1 CMOLXROSUKSQJU-UHFFFAOYSA-N 0.000 claims 2
• YVIDARGTGQKWAU-UHFFFAOYSA-N 3-[[3,5-dimethyl-4-(4-methylpiperazine-1-carbonyl)-1h-pyrrol-2-yl]methylidene]-4-(3-fluorophenyl)-1h-indol-2-one Chemical compound C1CN(C)CCN1C(=O)C1=C(C)NC(C=C2C3=C(C=CC=C3NC2=O)C=2C=C(F)C=CC=2)=C1C YVIDARGTGQKWAU-UHFFFAOYSA-N 0.000 claims 2
• QJDXAJSEIJIGGZ-UHFFFAOYSA-N 3-[[3,5-dimethyl-4-(4-methylpiperazine-1-carbonyl)-1h-pyrrol-2-yl]methylidene]-4-(3-methoxyphenyl)-1h-indol-2-one Chemical compound COC1=CC=CC(C=2C=3C(=CC4=C(C(C(=O)N5CCN(C)CC5)=C(C)N4)C)C(=O)NC=3C=CC=2)=C1 QJDXAJSEIJIGGZ-UHFFFAOYSA-N 0.000 claims 2
• NJSIYXJIHSXVLH-UHFFFAOYSA-N 3-[[3,5-dimethyl-4-(4-methylpiperazine-1-carbonyl)-1h-pyrrol-2-yl]methylidene]-4-(4-fluorophenyl)-1h-indol-2-one Chemical compound C1CN(C)CCN1C(=O)C1=C(C)NC(C=C2C3=C(C=CC=C3NC2=O)C=2C=CC(F)=CC=2)=C1C NJSIYXJIHSXVLH-UHFFFAOYSA-N 0.000 claims 2
• CCWBUISYAAUALO-UHFFFAOYSA-N 3-[[3,5-dimethyl-4-(4-methylpiperazine-1-carbonyl)-1h-pyrrol-2-yl]methylidene]-4-(4-methoxyphenyl)-1h-indol-2-one Chemical compound C1=CC(OC)=CC=C1C1=CC=CC(NC2=O)=C1C2=CC1=C(C)C(C(=O)N2CCN(C)CC2)=C(C)N1 CCWBUISYAAUALO-UHFFFAOYSA-N 0.000 claims 2
• ZJDMBWHFQMJBPH-UHFFFAOYSA-N 3-[[3,5-dimethyl-4-(4-methylpiperazine-1-carbonyl)-1h-pyrrol-2-yl]methylidene]-4-[3-(trifluoromethyl)phenyl]-1h-indol-2-one Chemical compound C1CN(C)CCN1C(=O)C1=C(C)NC(C=C2C3=C(C=CC=C3NC2=O)C=2C=C(C=CC=2)C(F)(F)F)=C1C ZJDMBWHFQMJBPH-UHFFFAOYSA-N 0.000 claims 2
• XJCSMRBRCNMPIL-UHFFFAOYSA-N 3-[[3,5-dimethyl-4-(4-methylpiperazine-1-carbonyl)-1h-pyrrol-2-yl]methylidene]-4-[4-(trifluoromethoxy)phenyl]-1h-indol-2-one Chemical compound C1CN(C)CCN1C(=O)C1=C(C)NC(C=C2C3=C(C=CC=C3NC2=O)C=2C=CC(OC(F)(F)F)=CC=2)=C1C XJCSMRBRCNMPIL-UHFFFAOYSA-N 0.000 claims 2
• VEMKJZMGZDCKEQ-UHFFFAOYSA-N 3-[[3,5-dimethyl-4-(4-methylpiperazine-1-carbonyl)-1h-pyrrol-2-yl]methylidene]-4-phenyl-1h-indol-2-one Chemical compound C1CN(C)CCN1C(=O)C1=C(C)NC(C=C2C3=C(C=CC=C3NC2=O)C=2C=CC=CC=2)=C1C VEMKJZMGZDCKEQ-UHFFFAOYSA-N 0.000 claims 2
• LJUXSADWDTYQAQ-LJQANCHMSA-N 3-[[3-[(3r)-3-(dimethylamino)pyrrolidine-1-carbonyl]-5-methyl-1h-pyrrol-2-yl]methylidene]-4-(3-fluorophenyl)-1h-indol-2-one Chemical compound C1[C@H](N(C)C)CCN1C(=O)C1=C(C=C2C3=C(C=CC=C3NC2=O)C=2C=C(F)C=CC=2)NC(C)=C1 LJUXSADWDTYQAQ-LJQANCHMSA-N 0.000 claims 2
• ZGWWWHVRMOHQTD-LJQANCHMSA-N 3-[[3-[(3r)-3-(dimethylamino)pyrrolidine-1-carbonyl]-5-methyl-1h-pyrrol-2-yl]methylidene]-4-(4-fluorophenyl)-1h-indol-2-one Chemical compound C1[C@H](N(C)C)CCN1C(=O)C1=C(C=C2C3=C(C=CC=C3NC2=O)C=2C=CC(F)=CC=2)NC(C)=C1 ZGWWWHVRMOHQTD-LJQANCHMSA-N 0.000 claims 2
• IAMVCPKGFHJBJS-LJQANCHMSA-N 3-[[3-[(3r)-3-(dimethylamino)pyrrolidine-1-carbonyl]-5-methyl-1h-pyrrol-2-yl]methylidene]-4-(4-methoxyphenyl)-1h-indol-2-one Chemical compound C1=CC(OC)=CC=C1C1=CC=CC(NC2=O)=C1C2=CC1=C(C(=O)N2C[C@@H](CC2)N(C)C)C=C(C)N1 IAMVCPKGFHJBJS-LJQANCHMSA-N 0.000 claims 2
• VDBPUKCYNGJKAD-CALCHBBNSA-N 3-[[3-[(3r,5s)-3,5-dimethylpiperazine-1-carbonyl]-5-methyl-1h-pyrrol-2-yl]methylidene]-4-(2-fluorophenyl)-1h-indol-2-one Chemical compound C1[C@@H](C)N[C@@H](C)CN1C(=O)C1=C(C=C2C3=C(C=CC=C3NC2=O)C=2C(=CC=CC=2)F)NC(C)=C1 VDBPUKCYNGJKAD-CALCHBBNSA-N 0.000 claims 2
• OMBFUKZWGIHJDZ-CALCHBBNSA-N 3-[[3-[(3r,5s)-3,5-dimethylpiperazine-1-carbonyl]-5-methyl-1h-pyrrol-2-yl]methylidene]-4-(3-fluorophenyl)-1h-indol-2-one Chemical compound C1[C@@H](C)N[C@@H](C)CN1C(=O)C1=C(C=C2C3=C(C=CC=C3NC2=O)C=2C=C(F)C=CC=2)NC(C)=C1 OMBFUKZWGIHJDZ-CALCHBBNSA-N 0.000 claims 2
• LJUXSADWDTYQAQ-IBGZPJMESA-N 3-[[3-[(3s)-3-(dimethylamino)pyrrolidine-1-carbonyl]-5-methyl-1h-pyrrol-2-yl]methylidene]-4-(3-fluorophenyl)-1h-indol-2-one Chemical compound C1[C@@H](N(C)C)CCN1C(=O)C1=C(C=C2C3=C(C=CC=C3NC2=O)C=2C=C(F)C=CC=2)NC(C)=C1 LJUXSADWDTYQAQ-IBGZPJMESA-N 0.000 claims 2
• ZGWWWHVRMOHQTD-IBGZPJMESA-N 3-[[3-[(3s)-3-(dimethylamino)pyrrolidine-1-carbonyl]-5-methyl-1h-pyrrol-2-yl]methylidene]-4-(4-fluorophenyl)-1h-indol-2-one Chemical compound C1[C@@H](N(C)C)CCN1C(=O)C1=C(C=C2C3=C(C=CC=C3NC2=O)C=2C=CC(F)=CC=2)NC(C)=C1 ZGWWWHVRMOHQTD-IBGZPJMESA-N 0.000 claims 2
• IAMVCPKGFHJBJS-IBGZPJMESA-N 3-[[3-[(3s)-3-(dimethylamino)pyrrolidine-1-carbonyl]-5-methyl-1h-pyrrol-2-yl]methylidene]-4-(4-methoxyphenyl)-1h-indol-2-one Chemical compound C1=CC(OC)=CC=C1C1=CC=CC(NC2=O)=C1C2=CC1=C(C(=O)N2C[C@H](CC2)N(C)C)C=C(C)N1 IAMVCPKGFHJBJS-IBGZPJMESA-N 0.000 claims 2
• FKZDPHCNJSKHMY-CALCHBBNSA-N 3-[[3-[(3s,5r)-3,5-dimethylpiperazine-1-carbonyl]-5-methyl-1h-pyrrol-2-yl]methylidene]-4-[2-(trifluoromethyl)phenyl]-1h-indol-2-one Chemical compound C1[C@@H](C)N[C@@H](C)CN1C(=O)C1=C(C=C2C3=C(C=CC=C3NC2=O)C=2C(=CC=CC=2)C(F)(F)F)NC(C)=C1 FKZDPHCNJSKHMY-CALCHBBNSA-N 0.000 claims 2
• BLGCOODZQHTUFQ-UHFFFAOYSA-N 3-[[3-methyl-4-(4-methylpiperazine-1-carbonyl)-1h-pyrrol-2-yl]methylidene]-4-[3-(trifluoromethyl)phenyl]-1h-indol-2-one Chemical compound C1CN(C)CCN1C(=O)C1=CNC(C=C2C3=C(C=CC=C3NC2=O)C=2C=C(C=CC=2)C(F)(F)F)=C1C BLGCOODZQHTUFQ-UHFFFAOYSA-N 0.000 claims 2
• DZCAHMJKIBPTJQ-UHFFFAOYSA-N 3-[[3-methyl-4-(4-methylpiperazine-1-carbonyl)-1h-pyrrol-2-yl]methylidene]-4-phenyl-1h-indol-2-one Chemical compound C1CN(C)CCN1C(=O)C1=CNC(C=C2C3=C(C=CC=C3NC2=O)C=2C=CC=CC=2)=C1C DZCAHMJKIBPTJQ-UHFFFAOYSA-N 0.000 claims 2
• YNQYKQKNMVRPNW-CALCHBBNSA-N 3-[[4-[(3r,5s)-3,5-dimethylpiperazine-1-carbonyl]-3,5-dimethyl-1h-pyrrol-2-yl]methylidene]-4-(3-methoxyphenyl)-1h-indol-2-one Chemical compound COC1=CC=CC(C=2C=3C(=CC4=C(C(C(=O)N5C[C@@H](C)N[C@@H](C)C5)=C(C)N4)C)C(=O)NC=3C=CC=2)=C1 YNQYKQKNMVRPNW-CALCHBBNSA-N 0.000 claims 2
• DFWFZVKBEXJMOJ-IYBDPMFKSA-N 3-[[4-[(3r,5s)-3,5-dimethylpiperazine-1-carbonyl]-3-methyl-1h-pyrrol-2-yl]methylidene]-4-[3-(trifluoromethyl)phenyl]-1h-indol-2-one Chemical compound C1[C@@H](C)N[C@@H](C)CN1C(=O)C1=CNC(C=C2C3=C(C=CC=C3NC2=O)C=2C=C(C=CC=2)C(F)(F)F)=C1C DFWFZVKBEXJMOJ-IYBDPMFKSA-N 0.000 claims 2
• QCCKYAKYZWEBIT-CALCHBBNSA-N 3-[[4-[(3r,5s)-3,5-dimethylpiperazine-1-carbonyl]-3-methyl-1h-pyrrol-2-yl]methylidene]-4-phenyl-1h-indol-2-one Chemical compound C1[C@@H](C)N[C@@H](C)CN1C(=O)C1=CNC(C=C2C3=C(C=CC=C3NC2=O)C=2C=CC=CC=2)=C1C QCCKYAKYZWEBIT-CALCHBBNSA-N 0.000 claims 2
• SLYDLEPXGOJXRI-CALCHBBNSA-N 3-[[4-[(3s,5r)-3,5-dimethylpiperazine-1-carbonyl]-3,5-dimethyl-1h-pyrrol-2-yl]methylidene]-4-(4-methoxyphenyl)-1h-indol-2-one Chemical compound C1=CC(OC)=CC=C1C1=CC=CC(NC2=O)=C1C2=CC1=C(C)C(C(=O)N2C[C@@H](C)N[C@@H](C)C2)=C(C)N1 SLYDLEPXGOJXRI-CALCHBBNSA-N 0.000 claims 2
• KCSJLVXBQWJCGN-CALCHBBNSA-N 3-[[4-[(3s,5r)-3,5-dimethylpiperazine-1-carbonyl]-3-methyl-1h-pyrrol-2-yl]methylidene]-4-(3-methoxyphenyl)-1h-indol-2-one Chemical compound COC1=CC=CC(C=2C=3C(=CC4=C(C(C(=O)N5C[C@@H](C)N[C@@H](C)C5)=CN4)C)C(=O)NC=3C=CC=2)=C1 KCSJLVXBQWJCGN-CALCHBBNSA-N 0.000 claims 2
• XAOJFMVPGDVMND-HDICACEKSA-N 3-[[4-[3-[(3r,5s)-3,5-dimethylpiperazin-1-yl]-3-oxopropyl]-3,5-dimethyl-1h-pyrrol-2-yl]methylidene]-4-(4-fluorophenyl)-1h-indol-2-one Chemical compound C1[C@@H](C)N[C@@H](C)CN1C(=O)CCC1=C(C)NC(C=C2C3=C(C=CC=C3NC2=O)C=2C=CC(F)=CC=2)=C1C XAOJFMVPGDVMND-HDICACEKSA-N 0.000 claims 2
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• QJISMICCTGLKAR-UHFFFAOYSA-N 4-(3-chlorophenyl)-3-[(3,5-dimethyl-1h-pyrrol-2-yl)methylidene]-1h-indol-2-one Chemical compound N1C(C)=CC(C)=C1C=C1C2=C(C=3C=C(Cl)C=CC=3)C=CC=C2NC1=O QJISMICCTGLKAR-UHFFFAOYSA-N 0.000 claims 2
• KVTXOWGRFOKFFI-UHFFFAOYSA-N 4-(3-chlorophenyl)-3-[[3,5-dimethyl-4-(4-methylpiperazine-1-carbonyl)-1h-pyrrol-2-yl]methylidene]-1h-indol-2-one Chemical compound C1CN(C)CCN1C(=O)C1=C(C)NC(C=C2C3=C(C=CC=C3NC2=O)C=2C=C(Cl)C=CC=2)=C1C KVTXOWGRFOKFFI-UHFFFAOYSA-N 0.000 claims 2
• HZLXFVVLABVCMU-IAGOWNOFSA-N 4-(3-chlorophenyl)-3-[[3-[(3R,5R)-3,5-dimethylpiperazine-1-carbonyl]-5-methyl-1H-pyrrol-2-yl]methylidene]-1H-indol-2-one Chemical compound C1[C@@H](C)N[C@H](C)CN1C(=O)C1=C(C=C2C3=C(C=CC=C3NC2=O)C=2C=C(Cl)C=CC=2)NC(C)=C1 HZLXFVVLABVCMU-IAGOWNOFSA-N 0.000 claims 2
• QMVTUXWKDHOZQN-LJQANCHMSA-N 4-(3-chlorophenyl)-3-[[3-[(3r)-3-(dimethylamino)pyrrolidine-1-carbonyl]-5-methyl-1h-pyrrol-2-yl]methylidene]-1h-indol-2-one Chemical compound C1[C@H](N(C)C)CCN1C(=O)C1=C(C=C2C3=C(C=CC=C3NC2=O)C=2C=C(Cl)C=CC=2)NC(C)=C1 QMVTUXWKDHOZQN-LJQANCHMSA-N 0.000 claims 2
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• QMVTUXWKDHOZQN-IBGZPJMESA-N 4-(3-chlorophenyl)-3-[[3-[(3s)-3-(dimethylamino)pyrrolidine-1-carbonyl]-5-methyl-1h-pyrrol-2-yl]methylidene]-1h-indol-2-one Chemical compound C1[C@@H](N(C)C)CCN1C(=O)C1=C(C=C2C3=C(C=CC=C3NC2=O)C=2C=C(Cl)C=CC=2)NC(C)=C1 QMVTUXWKDHOZQN-IBGZPJMESA-N 0.000 claims 2
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• AIPDNOFTRWLETR-UHFFFAOYSA-N 4-(4-bromophenyl)-3-[[3,5-dimethyl-4-(4-methylpiperazine-1-carbonyl)-1h-pyrrol-2-yl]methylidene]-1h-indol-2-one Chemical compound C1CN(C)CCN1C(=O)C1=C(C)NC(C=C2C3=C(C=CC=C3NC2=O)C=2C=CC(Br)=CC=2)=C1C AIPDNOFTRWLETR-UHFFFAOYSA-N 0.000 claims 2
• PYRUMMLWBZKXMA-UHFFFAOYSA-N 4-(4-chlorophenyl)-3-[(3,5-dimethyl-1h-pyrrol-2-yl)methylidene]-1h-indol-2-one Chemical compound N1C(C)=CC(C)=C1C=C1C2=C(C=3C=CC(Cl)=CC=3)C=CC=C2NC1=O PYRUMMLWBZKXMA-UHFFFAOYSA-N 0.000 claims 2
• KCOSXZYTSFJIAQ-UHFFFAOYSA-N 4-(4-chlorophenyl)-3-[[3,5-dimethyl-4-(4-methylpiperazine-1-carbonyl)-1h-pyrrol-2-yl]methylidene]-1h-indol-2-one Chemical compound C1CN(C)CCN1C(=O)C1=C(C)NC(C=C2C3=C(C=CC=C3NC2=O)C=2C=CC(Cl)=CC=2)=C1C KCOSXZYTSFJIAQ-UHFFFAOYSA-N 0.000 claims 2
• CARQSIFVDPCMTO-CALCHBBNSA-N 4-(4-chlorophenyl)-3-[[3-[(3r,5s)-3,5-dimethylpiperazine-1-carbonyl]-5-methyl-1h-pyrrol-2-yl]methylidene]-1h-indol-2-one Chemical compound C1[C@@H](C)N[C@@H](C)CN1C(=O)C1=C(C=C2C3=C(C=CC=C3NC2=O)C=2C=CC(Cl)=CC=2)NC(C)=C1 CARQSIFVDPCMTO-CALCHBBNSA-N 0.000 claims 2
• ARSWWAFXDHLACQ-UHFFFAOYSA-N 4-(4-chlorophenyl)-3-[[3-[3-(dimethylamino)pyrrolidine-1-carbonyl]-5-methyl-1h-pyrrol-2-yl]methylidene]-1h-indol-2-one Chemical compound C1C(N(C)C)CCN1C(=O)C1=C(C=C2C3=C(C=CC=C3NC2=O)C=2C=CC(Cl)=CC=2)NC(C)=C1 ARSWWAFXDHLACQ-UHFFFAOYSA-N 0.000 claims 2
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• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 2
• WLWXSMOKBLVBLG-UHFFFAOYSA-N 5-[[4-(2-fluorophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-2,4-dimethyl-n-(2-pyrrolidin-1-ylethyl)-1h-pyrrole-3-carboxamide Chemical compound CC=1C(C(=O)NCCN2CCCC2)=C(C)NC=1C=C(C=12)C(=O)NC2=CC=CC=1C1=CC=CC=C1F WLWXSMOKBLVBLG-UHFFFAOYSA-N 0.000 claims 2
• QFNIXCSLUXPKMD-UHFFFAOYSA-N 5-[[4-(2-fluorophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-2,4-dimethyl-n-[2-(triazol-1-yl)ethyl]-1h-pyrrole-3-carboxamide Chemical compound CC=1C(C(=O)NCCN2N=NC=C2)=C(C)NC=1C=C(C=12)C(=O)NC2=CC=CC=1C1=CC=CC=C1F QFNIXCSLUXPKMD-UHFFFAOYSA-N 0.000 claims 2
• DEFZFCHNJLFHAJ-UHFFFAOYSA-N 5-[[4-(3-bromophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-2,4-dimethyl-n-(2-pyrrolidin-1-ylethyl)-1h-pyrrole-3-carboxamide Chemical compound CC=1C(C(=O)NCCN2CCCC2)=C(C)NC=1C=C(C=12)C(=O)NC2=CC=CC=1C1=CC=CC(Br)=C1 DEFZFCHNJLFHAJ-UHFFFAOYSA-N 0.000 claims 2
• WFZQPNOMKMAVOU-UHFFFAOYSA-N 5-[[4-(3-bromophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-2,4-dimethyl-n-[2-(triazol-1-yl)ethyl]-1h-pyrrole-3-carboxamide Chemical compound CC=1C(C(=O)NCCN2N=NC=C2)=C(C)NC=1C=C(C=12)C(=O)NC2=CC=CC=1C1=CC=CC(Br)=C1 WFZQPNOMKMAVOU-UHFFFAOYSA-N 0.000 claims 2
• AWYCLFAMYDCSKX-UHFFFAOYSA-N 5-[[4-(3-bromophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-n-[2-(diethylamino)ethyl]-2,4-dimethyl-1h-pyrrole-3-carboxamide Chemical compound CCN(CC)CCNC(=O)C1=C(C)NC(C=C2C3=C(C=CC=C3NC2=O)C=2C=C(Br)C=CC=2)=C1C AWYCLFAMYDCSKX-UHFFFAOYSA-N 0.000 claims 2
• CUFCCTHXUAFJLJ-UHFFFAOYSA-N 5-[[4-(3-bromophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-n-[2-(diethylamino)ethyl]-4-methyl-1h-pyrrole-2-carboxamide Chemical compound N1C(C(=O)NCCN(CC)CC)=CC(C)=C1C=C1C2=C(C=3C=C(Br)C=CC=3)C=CC=C2NC1=O CUFCCTHXUAFJLJ-UHFFFAOYSA-N 0.000 claims 2
• GQXOKVRXBNGUKS-UHFFFAOYSA-N 5-[[4-(3-bromophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-n-[2-(diethylamino)ethyl]-4-methyl-1h-pyrrole-3-carboxamide Chemical compound CCN(CC)CCNC(=O)C1=CNC(C=C2C3=C(C=CC=C3NC2=O)C=2C=C(Br)C=CC=2)=C1C GQXOKVRXBNGUKS-UHFFFAOYSA-N 0.000 claims 2
• XFEQVGJEDWJFRF-UHFFFAOYSA-N 5-[[4-(3-bromophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-n-[2-[di(propan-2-yl)amino]ethyl]-2,4-dimethyl-1h-pyrrole-3-carboxamide Chemical compound CC(C)N(C(C)C)CCNC(=O)C1=C(C)NC(C=C2C3=C(C=CC=C3NC2=O)C=2C=C(Br)C=CC=2)=C1C XFEQVGJEDWJFRF-UHFFFAOYSA-N 0.000 claims 2
• ZSOBEUVBFLDZKG-UHFFFAOYSA-N 5-[[4-(3-chlorophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-2,4-dimethyl-n-(2-pyrrolidin-1-ylethyl)-1h-pyrrole-3-carboxamide Chemical compound CC=1C(C(=O)NCCN2CCCC2)=C(C)NC=1C=C(C=12)C(=O)NC2=CC=CC=1C1=CC=CC(Cl)=C1 ZSOBEUVBFLDZKG-UHFFFAOYSA-N 0.000 claims 2
• BDGRZJYHUQWMSF-UHFFFAOYSA-N 5-[[4-(3-chlorophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-2,4-dimethyl-n-[2-(triazol-1-yl)ethyl]-1h-pyrrole-3-carboxamide Chemical compound CC=1C(C(=O)NCCN2N=NC=C2)=C(C)NC=1C=C(C=12)C(=O)NC2=CC=CC=1C1=CC=CC(Cl)=C1 BDGRZJYHUQWMSF-UHFFFAOYSA-N 0.000 claims 2
• JJQTZFQPHKGKGR-UHFFFAOYSA-N 5-[[4-(3-chlorophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-n-[2-(diethylamino)ethyl]-2,4-dimethyl-1h-pyrrole-3-carboxamide Chemical compound CCN(CC)CCNC(=O)C1=C(C)NC(C=C2C3=C(C=CC=C3NC2=O)C=2C=C(Cl)C=CC=2)=C1C JJQTZFQPHKGKGR-UHFFFAOYSA-N 0.000 claims 2
• VFAMPYXSRROHHJ-UHFFFAOYSA-N 5-[[4-(3-chlorophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-n-[2-(diethylamino)ethyl]-4-methyl-1h-pyrrole-2-carboxamide Chemical compound N1C(C(=O)NCCN(CC)CC)=CC(C)=C1C=C1C2=C(C=3C=C(Cl)C=CC=3)C=CC=C2NC1=O VFAMPYXSRROHHJ-UHFFFAOYSA-N 0.000 claims 2
• XJBVXQYQPFWCBV-UHFFFAOYSA-N 5-[[4-(3-fluorophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-2,4-dimethyl-n-(2-pyrrolidin-1-ylethyl)-1h-pyrrole-3-carboxamide Chemical compound CC=1C(C(=O)NCCN2CCCC2)=C(C)NC=1C=C(C=12)C(=O)NC2=CC=CC=1C1=CC=CC(F)=C1 XJBVXQYQPFWCBV-UHFFFAOYSA-N 0.000 claims 2
• WPYLPWMWIMWBQX-UHFFFAOYSA-N 5-[[4-(3-fluorophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-2,4-dimethyl-n-[2-(triazol-1-yl)ethyl]-1h-pyrrole-3-carboxamide Chemical compound CC=1C(C(=O)NCCN2N=NC=C2)=C(C)NC=1C=C(C=12)C(=O)NC2=CC=CC=1C1=CC=CC(F)=C1 WPYLPWMWIMWBQX-UHFFFAOYSA-N 0.000 claims 2
• QMZCTQSEYLDFOE-UHFFFAOYSA-N 5-[[4-(3-methoxyphenyl)-2-oxo-1h-indol-3-ylidene]methyl]-2,4-dimethyl-n-(2-pyrrolidin-1-ylethyl)-1h-pyrrole-3-carboxamide Chemical compound COC1=CC=CC(C=2C=3C(=CC4=C(C(C(=O)NCCN5CCCC5)=C(C)N4)C)C(=O)NC=3C=CC=2)=C1 QMZCTQSEYLDFOE-UHFFFAOYSA-N 0.000 claims 2
• LVNMLQQLFIRBPP-UHFFFAOYSA-N 5-[[4-(4-bromophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-2,4-dimethyl-n-(2-pyrrolidin-1-ylethyl)-1h-pyrrole-3-carboxamide Chemical compound CC=1C(C(=O)NCCN2CCCC2)=C(C)NC=1C=C(C=12)C(=O)NC2=CC=CC=1C1=CC=C(Br)C=C1 LVNMLQQLFIRBPP-UHFFFAOYSA-N 0.000 claims 2
• HNZHSZTYPYDFTI-UHFFFAOYSA-N 5-[[4-(4-bromophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-2,4-dimethyl-n-[2-(triazol-1-yl)ethyl]-1h-pyrrole-3-carboxamide Chemical compound CC=1C(C(=O)NCCN2N=NC=C2)=C(C)NC=1C=C(C=12)C(=O)NC2=CC=CC=1C1=CC=C(Br)C=C1 HNZHSZTYPYDFTI-UHFFFAOYSA-N 0.000 claims 2
• OUVLIBRKOAFLHR-UHFFFAOYSA-N 5-[[4-(4-bromophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-n-[2-(diethylamino)ethyl]-4-methyl-1h-pyrrole-2-carboxamide Chemical compound N1C(C(=O)NCCN(CC)CC)=CC(C)=C1C=C1C2=C(C=3C=CC(Br)=CC=3)C=CC=C2NC1=O OUVLIBRKOAFLHR-UHFFFAOYSA-N 0.000 claims 2
• SOSORVXSSPVFSL-UHFFFAOYSA-N 5-[[4-(4-bromophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-n-[2-(diethylamino)ethyl]-4-methyl-1h-pyrrole-3-carboxamide Chemical compound CCN(CC)CCNC(=O)C1=CNC(C=C2C3=C(C=CC=C3NC2=O)C=2C=CC(Br)=CC=2)=C1C SOSORVXSSPVFSL-UHFFFAOYSA-N 0.000 claims 2
• UEBKKWXOGFGPLB-UHFFFAOYSA-N 5-[[4-(4-bromophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-n-[2-[di(propan-2-yl)amino]ethyl]-2,4-dimethyl-1h-pyrrole-3-carboxamide Chemical compound CC(C)N(C(C)C)CCNC(=O)C1=C(C)NC(C=C2C3=C(C=CC=C3NC2=O)C=2C=CC(Br)=CC=2)=C1C UEBKKWXOGFGPLB-UHFFFAOYSA-N 0.000 claims 2
• OBCKTIXGGXOFNS-UHFFFAOYSA-N 5-[[4-(4-chlorophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-2,4-dimethyl-n-(2-pyrrolidin-1-ylethyl)-1h-pyrrole-3-carboxamide Chemical compound CC=1C(C(=O)NCCN2CCCC2)=C(C)NC=1C=C(C=12)C(=O)NC2=CC=CC=1C1=CC=C(Cl)C=C1 OBCKTIXGGXOFNS-UHFFFAOYSA-N 0.000 claims 2
• UFXFNBBKXWFJPQ-UHFFFAOYSA-N 5-[[4-(4-chlorophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-2,4-dimethyl-n-[2-(triazol-1-yl)ethyl]-1h-pyrrole-3-carboxamide Chemical compound CC=1C(C(=O)NCCN2N=NC=C2)=C(C)NC=1C=C(C=12)C(=O)NC2=CC=CC=1C1=CC=C(Cl)C=C1 UFXFNBBKXWFJPQ-UHFFFAOYSA-N 0.000 claims 2
• JODQXLJXWOHIQA-UHFFFAOYSA-N 5-[[4-(4-chlorophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-n-[2-(diethylamino)ethyl]-4-methyl-1h-pyrrole-3-carboxamide Chemical compound CCN(CC)CCNC(=O)C1=CNC(C=C2C3=C(C=CC=C3NC2=O)C=2C=CC(Cl)=CC=2)=C1C JODQXLJXWOHIQA-UHFFFAOYSA-N 0.000 claims 2
• GGKBYFREOLROPM-UHFFFAOYSA-N 5-[[4-(4-fluorophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-2,4-dimethyl-n-(2-pyrrolidin-1-ylethyl)-1h-pyrrole-3-carboxamide Chemical compound CC=1C(C(=O)NCCN2CCCC2)=C(C)NC=1C=C(C=12)C(=O)NC2=CC=CC=1C1=CC=C(F)C=C1 GGKBYFREOLROPM-UHFFFAOYSA-N 0.000 claims 2
• HRFPMFRICRAWSH-UHFFFAOYSA-N 5-[[4-(4-fluorophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-2,4-dimethyl-n-[2-(triazol-1-yl)ethyl]-1h-pyrrole-3-carboxamide Chemical compound CC=1C(C(=O)NCCN2N=NC=C2)=C(C)NC=1C=C(C=12)C(=O)NC2=CC=CC=1C1=CC=C(F)C=C1 HRFPMFRICRAWSH-UHFFFAOYSA-N 0.000 claims 2
• IUGNYQNBTJKTAZ-UHFFFAOYSA-N 5-[[4-(4-methoxyphenyl)-2-oxo-1h-indol-3-ylidene]methyl]-2,4-dimethyl-n-(2-pyrrolidin-1-ylethyl)-1h-pyrrole-3-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=CC=CC(NC2=O)=C1C2=CC1=C(C)C(C(=O)NCCN2CCCC2)=C(C)N1 IUGNYQNBTJKTAZ-UHFFFAOYSA-N 0.000 claims 2
• KMDVLJJBIFZTEM-UHFFFAOYSA-N 5-[[4-(4-methoxyphenyl)-2-oxo-1h-indol-3-ylidene]methyl]-2,4-dimethyl-n-[2-(triazol-1-yl)ethyl]-1h-pyrrole-3-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=CC=CC(NC2=O)=C1C2=CC1=C(C)C(C(=O)NCCN2N=NC=C2)=C(C)N1 KMDVLJJBIFZTEM-UHFFFAOYSA-N 0.000 claims 2
• ZPRBNCGDKRGESP-UHFFFAOYSA-N 5-methyl-2-[[2-oxo-4-[3-(trifluoromethyl)phenyl]-1h-indol-3-ylidene]methyl]-n-(2-pyrrolidin-1-ylethyl)-1h-pyrrole-3-carboxamide Chemical compound O=C1NC2=CC=CC(C=3C=C(C=CC=3)C(F)(F)F)=C2C1=CC=1NC(C)=CC=1C(=O)NCCN1CCCC1 ZPRBNCGDKRGESP-UHFFFAOYSA-N 0.000 claims 2
• FRZGXKVFKXYVCL-UHFFFAOYSA-N 5-methyl-2-[[2-oxo-4-[3-(trifluoromethyl)phenyl]-1h-indol-3-ylidene]methyl]-n-(3-pyrrolidin-1-ylpropyl)-1h-pyrrole-3-carboxamide Chemical compound O=C1NC2=CC=CC(C=3C=C(C=CC=3)C(F)(F)F)=C2C1=CC=1NC(C)=CC=1C(=O)NCCCN1CCCC1 FRZGXKVFKXYVCL-UHFFFAOYSA-N 0.000 claims 2
• DDUVWBLVCFRLEO-UHFFFAOYSA-N 5-methyl-2-[[2-oxo-4-[3-(trifluoromethyl)phenyl]-1h-indol-3-ylidene]methyl]-n-[2-(triazol-1-yl)ethyl]-1h-pyrrole-3-carboxamide Chemical compound O=C1NC2=CC=CC(C=3C=C(C=CC=3)C(F)(F)F)=C2C1=CC=1NC(C)=CC=1C(=O)NCCN1C=CN=N1 DDUVWBLVCFRLEO-UHFFFAOYSA-N 0.000 claims 2
• TXDSRWOURBZAGH-UHFFFAOYSA-N 5-methyl-2-[[2-oxo-4-[4-(trifluoromethoxy)phenyl]-1h-indol-3-ylidene]methyl]-n-(2-pyrrolidin-1-ylethyl)-1h-pyrrole-3-carboxamide Chemical compound O=C1NC2=CC=CC(C=3C=CC(OC(F)(F)F)=CC=3)=C2C1=CC=1NC(C)=CC=1C(=O)NCCN1CCCC1 TXDSRWOURBZAGH-UHFFFAOYSA-N 0.000 claims 2
• HIUSMASHEKDDAT-UHFFFAOYSA-N 5-methyl-2-[[2-oxo-4-[4-(trifluoromethoxy)phenyl]-1h-indol-3-ylidene]methyl]-n-(3-pyrrolidin-1-ylpropyl)-1h-pyrrole-3-carboxamide Chemical compound O=C1NC2=CC=CC(C=3C=CC(OC(F)(F)F)=CC=3)=C2C1=CC=1NC(C)=CC=1C(=O)NCCCN1CCCC1 HIUSMASHEKDDAT-UHFFFAOYSA-N 0.000 claims 2
• ROBBRJCFIFFCQA-UHFFFAOYSA-N 5-methyl-2-[[2-oxo-4-[4-(trifluoromethoxy)phenyl]-1h-indol-3-ylidene]methyl]-n-[2-(triazol-1-yl)ethyl]-1h-pyrrole-3-carboxamide Chemical compound O=C1NC2=CC=CC(C=3C=CC(OC(F)(F)F)=CC=3)=C2C1=CC=1NC(C)=CC=1C(=O)NCCN1C=CN=N1 ROBBRJCFIFFCQA-UHFFFAOYSA-N 0.000 claims 2
• OJQUTFZAUFDLMV-UHFFFAOYSA-N ethyl 5-[[4-(3-fluorophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-2-methyl-4-[3-(4-methylpiperazin-1-yl)propyl]-1h-pyrrole-3-carboxylate Chemical compound C1CN(C)CCN1CCCC=1C(C(=O)OCC)=C(C)NC=1C=C(C=12)C(=O)NC2=CC=CC=1C1=CC=CC(F)=C1 OJQUTFZAUFDLMV-UHFFFAOYSA-N 0.000 claims 2
• IDZYIGNQESDESB-UHFFFAOYSA-N ethyl 5-[[4-(4-chlorophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-2-methyl-4-[3-(4-methylpiperazin-1-yl)propyl]-1h-pyrrole-3-carboxylate Chemical compound C1CN(C)CCN1CCCC=1C(C(=O)OCC)=C(C)NC=1C=C(C=12)C(=O)NC2=CC=CC=1C1=CC=C(Cl)C=C1 IDZYIGNQESDESB-UHFFFAOYSA-N 0.000 claims 2
• SOOSPVAROQQHLY-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]-2,4-dimethyl-5-[(2-oxo-4-phenyl-1h-indol-3-ylidene)methyl]-1h-pyrrole-3-carboxamide Chemical compound CCN(CC)CCNC(=O)C1=C(C)NC(C=C2C3=C(C=CC=C3NC2=O)C=2C=CC=CC=2)=C1C SOOSPVAROQQHLY-UHFFFAOYSA-N 0.000 claims 2
• HAKKNBXVBAEQBF-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]-2-[[4-(2-fluorophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-5-methyl-1h-pyrrole-3-carboxamide Chemical compound C1=C(C)NC(C=C2C3=C(C=CC=C3NC2=O)C=2C(=CC=CC=2)F)=C1C(=O)NCCN(CC)CC HAKKNBXVBAEQBF-UHFFFAOYSA-N 0.000 claims 2
• AUBTYVBSUQIKOG-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]-5-[[4-(2-fluorophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-2,4-dimethyl-1h-pyrrole-3-carboxamide Chemical compound CCN(CC)CCNC(=O)C1=C(C)NC(C=C2C3=C(C=CC=C3NC2=O)C=2C(=CC=CC=2)F)=C1C AUBTYVBSUQIKOG-UHFFFAOYSA-N 0.000 claims 2
• XNCPPDPYMCKGCU-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]-5-[[4-(3-fluorophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-2,4-dimethyl-1h-pyrrole-3-carboxamide Chemical compound CCN(CC)CCNC(=O)C1=C(C)NC(C=C2C3=C(C=CC=C3NC2=O)C=2C=C(F)C=CC=2)=C1C XNCPPDPYMCKGCU-UHFFFAOYSA-N 0.000 claims 2
• HVIPWBMWRSJICM-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]-5-[[4-(3-fluorophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-4-methyl-1h-pyrrole-2-carboxamide Chemical compound N1C(C(=O)NCCN(CC)CC)=CC(C)=C1C=C1C2=C(C=3C=C(F)C=CC=3)C=CC=C2NC1=O HVIPWBMWRSJICM-UHFFFAOYSA-N 0.000 claims 2
• QXBCDDPQIOQCGZ-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]-5-[[4-(3-fluorophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-4-methyl-1h-pyrrole-3-carboxamide Chemical compound CCN(CC)CCNC(=O)C1=CNC(C=C2C3=C(C=CC=C3NC2=O)C=2C=C(F)C=CC=2)=C1C QXBCDDPQIOQCGZ-UHFFFAOYSA-N 0.000 claims 2
• BTFQJMFLSFIAFC-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]-5-[[4-(3-methoxyphenyl)-2-oxo-1h-indol-3-ylidene]methyl]-2,4-dimethyl-1h-pyrrole-3-carboxamide Chemical compound CCN(CC)CCNC(=O)C1=C(C)NC(C=C2C3=C(C=CC=C3NC2=O)C=2C=C(OC)C=CC=2)=C1C BTFQJMFLSFIAFC-UHFFFAOYSA-N 0.000 claims 2
• ZUDDXDBTUNSDCG-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]-5-[[4-(3-methoxyphenyl)-2-oxo-1h-indol-3-ylidene]methyl]-4-methyl-1h-pyrrole-2-carboxamide Chemical compound N1C(C(=O)NCCN(CC)CC)=CC(C)=C1C=C1C2=C(C=3C=C(OC)C=CC=3)C=CC=C2NC1=O ZUDDXDBTUNSDCG-UHFFFAOYSA-N 0.000 claims 2
• UVKJLVZOOAHNTH-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]-5-[[4-(3-methoxyphenyl)-2-oxo-1h-indol-3-ylidene]methyl]-4-methyl-1h-pyrrole-3-carboxamide Chemical compound CCN(CC)CCNC(=O)C1=CNC(C=C2C3=C(C=CC=C3NC2=O)C=2C=C(OC)C=CC=2)=C1C UVKJLVZOOAHNTH-UHFFFAOYSA-N 0.000 claims 2
• NDOVTMAPELRORE-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]-5-[[4-(4-fluorophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-4-methyl-1h-pyrrole-2-carboxamide Chemical compound N1C(C(=O)NCCN(CC)CC)=CC(C)=C1C=C1C2=C(C=3C=CC(F)=CC=3)C=CC=C2NC1=O NDOVTMAPELRORE-UHFFFAOYSA-N 0.000 claims 2
• LQORWICAAMQPGZ-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]-5-[[4-(4-fluorophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-4-methyl-1h-pyrrole-3-carboxamide Chemical compound CCN(CC)CCNC(=O)C1=CNC(C=C2C3=C(C=CC=C3NC2=O)C=2C=CC(F)=CC=2)=C1C LQORWICAAMQPGZ-UHFFFAOYSA-N 0.000 claims 2
• AKZFGZSUSNFQLF-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]-5-[[4-(4-methoxyphenyl)-2-oxo-1h-indol-3-ylidene]methyl]-2,4-dimethyl-1h-pyrrole-3-carboxamide Chemical compound CCN(CC)CCNC(=O)C1=C(C)NC(C=C2C3=C(C=CC=C3NC2=O)C=2C=CC(OC)=CC=2)=C1C AKZFGZSUSNFQLF-UHFFFAOYSA-N 0.000 claims 2
• AAOPBDUQPCGXPJ-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]-5-[[4-(4-methoxyphenyl)-2-oxo-1h-indol-3-ylidene]methyl]-4-methyl-1h-pyrrole-2-carboxamide Chemical compound N1C(C(=O)NCCN(CC)CC)=CC(C)=C1C=C1C2=C(C=3C=CC(OC)=CC=3)C=CC=C2NC1=O AAOPBDUQPCGXPJ-UHFFFAOYSA-N 0.000 claims 2
• FIQMYCYMAGZMSV-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]-5-[[4-(4-methoxyphenyl)-2-oxo-1h-indol-3-ylidene]methyl]-4-methyl-1h-pyrrole-3-carboxamide Chemical compound CCN(CC)CCNC(=O)C1=CNC(C=C2C3=C(C=CC=C3NC2=O)C=2C=CC(OC)=CC=2)=C1C FIQMYCYMAGZMSV-UHFFFAOYSA-N 0.000 claims 2
• DYVMJOLAUOFYTK-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]-5-methyl-2-[[2-oxo-4-[3-(trifluoromethyl)phenyl]-1h-indol-3-ylidene]methyl]-1h-pyrrole-3-carboxamide Chemical compound C1=C(C)NC(C=C2C3=C(C=CC=C3NC2=O)C=2C=C(C=CC=2)C(F)(F)F)=C1C(=O)NCCN(CC)CC DYVMJOLAUOFYTK-UHFFFAOYSA-N 0.000 claims 2
• WWGVQMBGZSNBOQ-UHFFFAOYSA-N n-[2-[di(propan-2-yl)amino]ethyl]-5-[[4-(3-methoxyphenyl)-2-oxo-1h-indol-3-ylidene]methyl]-2,4-dimethyl-1h-pyrrole-3-carboxamide Chemical compound COC1=CC=CC(C=2C=3C(=CC4=C(C(C(=O)NCCN(C(C)C)C(C)C)=C(C)N4)C)C(=O)NC=3C=CC=2)=C1 WWGVQMBGZSNBOQ-UHFFFAOYSA-N 0.000 claims 2
• CQMWTLFYAVCUQT-UHFFFAOYSA-N n-[3-(diethylamino)propyl]-2,4-dimethyl-5-[[2-oxo-4-[3-(trifluoromethyl)phenyl]-1h-indol-3-ylidene]methyl]-1h-pyrrole-3-carboxamide Chemical compound CCN(CC)CCCNC(=O)C1=C(C)NC(C=C2C3=C(C=CC=C3NC2=O)C=2C=C(C=CC=2)C(F)(F)F)=C1C CQMWTLFYAVCUQT-UHFFFAOYSA-N 0.000 claims 2
• HYGILJMGVAKPQK-UHFFFAOYSA-N n-[3-(diethylamino)propyl]-5-[[4-(3-fluorophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-2,4-dimethyl-1h-pyrrole-3-carboxamide Chemical compound CCN(CC)CCCNC(=O)C1=C(C)NC(C=C2C3=C(C=CC=C3NC2=O)C=2C=C(F)C=CC=2)=C1C HYGILJMGVAKPQK-UHFFFAOYSA-N 0.000 claims 2
• SHIHTYTZPVUSSO-UHFFFAOYSA-N n-[3-(diethylamino)propyl]-5-[[4-(4-fluorophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-2,4-dimethyl-1h-pyrrole-3-carboxamide Chemical compound CCN(CC)CCCNC(=O)C1=C(C)NC(C=C2C3=C(C=CC=C3NC2=O)C=2C=CC(F)=CC=2)=C1C SHIHTYTZPVUSSO-UHFFFAOYSA-N 0.000 claims 2
• FTJZYVVSYGMTDG-UHFFFAOYSA-N 2-[[4-(3-chloro-4-fluorophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-5-methyl-n-(2-pyrrolidin-1-ylethyl)-1h-pyrrole-3-carboxamide Chemical compound O=C1NC2=CC=CC(C=3C=C(Cl)C(F)=CC=3)=C2C1=CC=1NC(C)=CC=1C(=O)NCCN1CCCC1 FTJZYVVSYGMTDG-UHFFFAOYSA-N 0.000 claims 1
• QHTXLBVVSUMSPK-UHFFFAOYSA-N 2-[[4-(3-chloro-4-fluorophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-5-methyl-n-(3-pyrrolidin-1-ylpropyl)-1h-pyrrole-3-carboxamide Chemical compound O=C1NC2=CC=CC(C=3C=C(Cl)C(F)=CC=3)=C2C1=CC=1NC(C)=CC=1C(=O)NCCCN1CCCC1 QHTXLBVVSUMSPK-UHFFFAOYSA-N 0.000 claims 1
• LUYJJXSLZQXIDX-UHFFFAOYSA-N 2-[[4-(3-chloro-4-fluorophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-5-methyl-n-[2-(triazol-1-yl)ethyl]-1h-pyrrole-3-carboxamide Chemical compound O=C1NC2=CC=CC(C=3C=C(Cl)C(F)=CC=3)=C2C1=CC=1NC(C)=CC=1C(=O)NCCN1C=CN=N1 LUYJJXSLZQXIDX-UHFFFAOYSA-N 0.000 claims 1
• PAYQSBWVABTJPX-UHFFFAOYSA-N 2-[[4-(4-methoxyphenyl)-2-oxo-1h-indol-3-ylidene]methyl]-5-methyl-n-(2-pyrrolidin-1-ylethyl)-1h-pyrrole-3-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=CC=CC(NC2=O)=C1C2=CC1=C(C(=O)NCCN2CCCC2)C=C(C)N1 PAYQSBWVABTJPX-UHFFFAOYSA-N 0.000 claims 1
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