AU2005318126B2 - Indolidone derivatives for the treatment or prevention of fibrotic diseases - Google Patents
Indolidone derivatives for the treatment or prevention of fibrotic diseases Download PDFInfo
- Publication number
- AU2005318126B2 AU2005318126B2 AU2005318126A AU2005318126A AU2005318126B2 AU 2005318126 B2 AU2005318126 B2 AU 2005318126B2 AU 2005318126 A AU2005318126 A AU 2005318126A AU 2005318126 A AU2005318126 A AU 2005318126A AU 2005318126 B2 AU2005318126 B2 AU 2005318126B2
- Authority
- AU
- Australia
- Prior art keywords
- phenyl
- methylene
- indolinone
- anilino
- amino
- 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.)
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- 230000002265 prevention Effects 0.000 title claims abstract description 14
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical class C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 title abstract description 75
- 230000003176 fibrotic effect Effects 0.000 title abstract description 18
- 201000010099 disease Diseases 0.000 title abstract description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 41
- 239000003814 drug Substances 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims description 100
- 239000000203 mixture Substances 0.000 claims description 52
- 239000013543 active substance Substances 0.000 claims description 35
- 125000001639 phenylmethylene group Chemical group [H]C(=*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 19
- 239000005557 antagonist Substances 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 14
- 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 11
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims description 9
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims description 9
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 claims description 6
- 108010068338 p38 Mitogen-Activated Protein Kinases Proteins 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 5
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 claims description 4
- 239000000812 cholinergic antagonist Substances 0.000 claims description 4
- 229940121647 egfr inhibitor Drugs 0.000 claims description 4
- YEESKJGWJFYOOK-IJHYULJSSA-N leukotriene D4 Chemical compound CCCCC\C=C/C\C=C/C=C/C=C/[C@H]([C@@H](O)CCCC(O)=O)SC[C@H](N)C(=O)NCC(O)=O YEESKJGWJFYOOK-IJHYULJSSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000002829 mitogen activated protein kinase inhibitor Substances 0.000 claims description 4
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims description 4
- 150000003431 steroids Chemical class 0.000 claims description 4
- 239000000969 carrier Substances 0.000 claims description 2
- -1 Ci- 3 -alkoxy Chemical group 0.000 description 285
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 178
- JJCVYMJAZLMUST-UHFFFAOYSA-N methyl 2-oxo-3h-indole-1-carboxylate Chemical compound C1=CC=C2N(C(=O)OC)C(=O)CC2=C1 JJCVYMJAZLMUST-UHFFFAOYSA-N 0.000 description 115
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 105
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 105
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 87
- RNSNPSMLRZWYGB-UHFFFAOYSA-N ethyl 2-oxo-3h-indole-1-carboxylate Chemical compound C1=CC=C2N(C(=O)OCC)C(=O)CC2=C1 RNSNPSMLRZWYGB-UHFFFAOYSA-N 0.000 description 84
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 77
- 125000000217 alkyl group Chemical group 0.000 description 70
- BAJMJTSRFSOEAU-DQRAZIAOSA-N ethyl (3z)-3-[(4-chloroanilino)-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(Cl)C=C1 BAJMJTSRFSOEAU-DQRAZIAOSA-N 0.000 description 67
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 63
- QYLAOEXGMQWKHB-DQRAZIAOSA-N ethyl (3z)-2-oxo-3-[phenyl-[4-(trifluoromethyl)anilino]methylidene]-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(C(F)(F)F)C=C1 QYLAOEXGMQWKHB-DQRAZIAOSA-N 0.000 description 51
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 40
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 39
- 125000006842 cycloalkyleneimino group Chemical group 0.000 description 38
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 36
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 35
- 229960001866 silicon dioxide Drugs 0.000 description 32
- 125000001072 heteroaryl group Chemical group 0.000 description 31
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 28
- 239000000741 silica gel Substances 0.000 description 28
- 229910002027 silica gel Inorganic materials 0.000 description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 27
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 27
- 229910052760 oxygen Inorganic materials 0.000 description 27
- 239000001301 oxygen Substances 0.000 description 27
- 238000002360 preparation method Methods 0.000 description 23
- 229910052801 chlorine Inorganic materials 0.000 description 22
- 229910052757 nitrogen Inorganic materials 0.000 description 22
- 108010006654 Bleomycin Proteins 0.000 description 21
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 21
- 125000004433 nitrogen atom Chemical group N* 0.000 description 21
- 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 description 20
- OYVAGSVQBOHSSS-UAPAGMARSA-O bleomycin A2 Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C OYVAGSVQBOHSSS-UAPAGMARSA-O 0.000 description 20
- PUKHGNSTFYBFJY-DQRAZIAOSA-N ethyl (3z)-3-[(4-nitroanilino)-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C([N+]([O-])=O)C=C1 PUKHGNSTFYBFJY-DQRAZIAOSA-N 0.000 description 20
- 206010016654 Fibrosis Diseases 0.000 description 19
- 229960001561 bleomycin Drugs 0.000 description 19
- 239000000460 chlorine Substances 0.000 description 19
- 230000004761 fibrosis Effects 0.000 description 19
- 229910052731 fluorine Inorganic materials 0.000 description 19
- 239000011737 fluorine Substances 0.000 description 19
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 18
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 18
- 238000001819 mass spectrum Methods 0.000 description 17
- 239000007858 starting material Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 125000004093 cyano group Chemical group *C#N 0.000 description 16
- 210000004072 lung Anatomy 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- 239000003826 tablet Substances 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- 230000014509 gene expression Effects 0.000 description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 15
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 15
- 208000005069 pulmonary fibrosis Diseases 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 14
- NLESELGCGYIEST-UHFFFAOYSA-N 3-ethyl-N-methyl-2-oxo-3H-indole-1-carboxamide Chemical compound C(C)C1C(N(C2=CC=CC=C12)C(NC)=O)=O NLESELGCGYIEST-UHFFFAOYSA-N 0.000 description 13
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 13
- 241000700159 Rattus Species 0.000 description 13
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 13
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 13
- 125000003118 aryl group Chemical group 0.000 description 13
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 13
- 229910052794 bromium Inorganic materials 0.000 description 13
- 239000002775 capsule Substances 0.000 description 13
- 125000000623 heterocyclic group Chemical group 0.000 description 13
- 229910052739 hydrogen Inorganic materials 0.000 description 13
- 239000001257 hydrogen Substances 0.000 description 13
- 125000001841 imino group Chemical group [H]N=* 0.000 description 13
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 125000003790 chinazolinyl group Chemical group 0.000 description 12
- 229910052740 iodine Inorganic materials 0.000 description 12
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 12
- 210000001519 tissue Anatomy 0.000 description 12
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 11
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
- 125000000753 cycloalkyl group Chemical group 0.000 description 11
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 11
- 125000001424 substituent group Chemical group 0.000 description 11
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 10
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- 239000000523 sample Substances 0.000 description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 9
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 9
- 229910021529 ammonia Inorganic materials 0.000 description 9
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 9
- 239000002299 complementary DNA Substances 0.000 description 9
- 125000001153 fluoro group Chemical group F* 0.000 description 9
- 239000008101 lactose Substances 0.000 description 9
- 125000001624 naphthyl group Chemical group 0.000 description 9
- 239000011780 sodium chloride Substances 0.000 description 9
- 239000003981 vehicle Substances 0.000 description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 150000002431 hydrogen Chemical class 0.000 description 8
- UTEHGZFZMLODQF-VHXPQNKSSA-N methyl (3z)-3-[[4-(1-methylimidazol-2-yl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1C1=NC=CN1C UTEHGZFZMLODQF-VHXPQNKSSA-N 0.000 description 8
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 8
- OSCBITMSEJEECJ-UHFFFAOYSA-N n-ethyl-2-oxo-3h-indole-1-carboxamide Chemical compound C1=CC=C2N(C(=O)NCC)C(=O)CC2=C1 OSCBITMSEJEECJ-UHFFFAOYSA-N 0.000 description 8
- 102000010834 Extracellular Matrix Proteins Human genes 0.000 description 7
- 108010037362 Extracellular Matrix Proteins Proteins 0.000 description 7
- 125000003545 alkoxy group Chemical group 0.000 description 7
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 7
- 210000004027 cell Anatomy 0.000 description 7
- 125000002993 cycloalkylene group Chemical group 0.000 description 7
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- 235000019359 magnesium stearate Nutrition 0.000 description 7
- UDRYCALAFSXOJU-IZHYLOQSSA-N methyl (3z)-3-[[4-[2-(dimethylamino)ethoxy]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(OCCN(C)C)C=C1 UDRYCALAFSXOJU-IZHYLOQSSA-N 0.000 description 7
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 7
- 108090000623 proteins and genes Proteins 0.000 description 7
- ISWQKKSKJPFNDQ-RQZHXJHFSA-N (3z)-3-[[4-[2-(dimethylamino)ethoxy]anilino]-phenylmethylidene]-6-ethyl-n-methyl-2-oxoindole-1-carboxamide Chemical compound O=C1N(C(=O)NC)C2=CC(CC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(OCCN(C)C)C=C1 ISWQKKSKJPFNDQ-RQZHXJHFSA-N 0.000 description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 6
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 230000008021 deposition Effects 0.000 description 6
- OAQGXSYPNXOVNI-FCQUAONHSA-N ethyl (3z)-3-[(4-methoxyanilino)-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(OC)C=C1 OAQGXSYPNXOVNI-FCQUAONHSA-N 0.000 description 6
- 125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 description 6
- 210000002744 extracellular matrix Anatomy 0.000 description 6
- 210000002950 fibroblast Anatomy 0.000 description 6
- 238000001727 in vivo Methods 0.000 description 6
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 6
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- ASRXXPJYKGEPRA-VHXPQNKSSA-N (3z)-3-[[4-(3-amino-1,5-dihydroxypentan-3-yl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylic acid Chemical compound C1=CC(C(CCO)(CCO)N)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(O)=O)C=C2NC\1=O ASRXXPJYKGEPRA-VHXPQNKSSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 102000016359 Fibronectins Human genes 0.000 description 5
- 108010067306 Fibronectins Proteins 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
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- 125000003282 alkyl amino group Chemical group 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- NALBLJLOBICXRH-UHFFFAOYSA-N dinitrogen monohydride Chemical group N=[N] NALBLJLOBICXRH-UHFFFAOYSA-N 0.000 description 5
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- 239000000725 suspension Substances 0.000 description 5
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 5
- ZRKFYGHZFMAOKI-QMGMOQQFSA-N tgfbeta Chemical compound C([C@H](NC(=O)[C@H](C(C)C)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](N)CCSC)C(C)C)[C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(O)=O)C1=CC=C(O)C=C1 ZRKFYGHZFMAOKI-QMGMOQQFSA-N 0.000 description 5
- VHPSFIVOKPGFEG-DQRAZIAOSA-N (3z)-3-[[4-(methylaminomethyl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylic acid Chemical compound C1=CC(CNC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(O)=O)C=C2NC\1=O VHPSFIVOKPGFEG-DQRAZIAOSA-N 0.000 description 4
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- LDLGHKOPBXJLSS-FLWNBWAVSA-N ethyl (3z)-3-[[4-[(3,5-dimethylpiperidin-1-yl)methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CN1CC(C)CC(C)C1 LDLGHKOPBXJLSS-FLWNBWAVSA-N 0.000 description 2
- XMPWEPBXDKUKDD-DQSJHHFOSA-N ethyl (3z)-3-[[4-[(4-hydroxypiperidin-1-yl)methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CN1CCC(O)CC1 XMPWEPBXDKUKDD-DQSJHHFOSA-N 0.000 description 2
- OTTBHEFDQWWXLM-FCQUAONHSA-N ethyl (3z)-3-[[4-[(carbamoylamino)methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CNC(N)=O)C=C1 OTTBHEFDQWWXLM-FCQUAONHSA-N 0.000 description 2
- SPJJQQSCEAHBGT-ZIADKAODSA-N ethyl (3z)-3-[[4-[(cyclohexylamino)methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CNC1CCCCC1 SPJJQQSCEAHBGT-ZIADKAODSA-N 0.000 description 2
- MKJUGJQVAVYLQO-KRYSQPQISA-N ethyl (3z)-3-[[4-[(dibenzylamino)methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CN(CC=1C=CC=CC=1)CC1=CC=CC=C1 MKJUGJQVAVYLQO-KRYSQPQISA-N 0.000 description 2
- KIIQDBPXYINGHU-IZHYLOQSSA-N ethyl (3z)-3-[[4-[(dimethylamino)methyl]-3-(trifluoromethyl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(C)C)C(C(F)(F)F)=C1 KIIQDBPXYINGHU-IZHYLOQSSA-N 0.000 description 2
- TXPJKUCTZAGEKA-IZHYLOQSSA-N ethyl (3z)-3-[[4-[(dimethylamino)methyl]-3-hydroxyanilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(C)C)C(O)=C1 TXPJKUCTZAGEKA-IZHYLOQSSA-N 0.000 description 2
- NOABLTZKCSKSNV-ZIADKAODSA-N ethyl (3z)-3-[[4-[(dipropylamino)methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(CN(CCC)CCC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OCC)C=C2NC\1=O NOABLTZKCSKSNV-ZIADKAODSA-N 0.000 description 2
- DIWHRMJVZVOQMR-DQSJHHFOSA-N ethyl (3z)-3-[[4-[1-amino-4-(dimethylamino)butyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(C(N)CCCN(C)C)C=C1 DIWHRMJVZVOQMR-DQSJHHFOSA-N 0.000 description 2
- LMPDBUQWXPQWRU-RQZHXJHFSA-N ethyl (3z)-3-[[4-[2-(1h-imidazol-5-yl)ethyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CCC1=CNC=N1 LMPDBUQWXPQWRU-RQZHXJHFSA-N 0.000 description 2
- PVQSVNCLFZCJRA-KARKAFJISA-N ethyl (3z)-3-[[4-[2-(dimethylamino)ethyl-(2-methoxybenzoyl)amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1N(CCN(C)C)C(=O)C1=CC=CC=C1OC PVQSVNCLFZCJRA-KARKAFJISA-N 0.000 description 2
- LYQURIDRDZOJCO-IZHYLOQSSA-N ethyl (3z)-3-[[4-[2-(methylamino)ethyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CCNC)C=C1 LYQURIDRDZOJCO-IZHYLOQSSA-N 0.000 description 2
- WJSIKXOMOMYGEP-IZHYLOQSSA-N ethyl (3z)-3-[[4-[2-amino-1-(dimethylamino)-1-oxopropan-2-yl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(C(C)(N)C(=O)N(C)C)C=C1 WJSIKXOMOMYGEP-IZHYLOQSSA-N 0.000 description 2
- JMNVGHSFRONZKH-IZHYLOQSSA-N ethyl (3z)-3-[[4-[2-aminoethyl(methylsulfonyl)amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(CCN)S(C)(=O)=O)C=C1 JMNVGHSFRONZKH-IZHYLOQSSA-N 0.000 description 2
- PVADCVQLBCMSHD-KTMFPKCZSA-N ethyl (3z)-3-[[4-[[2-(dimethylamino)-2-oxoethyl]-[3-(dimethylamino)propylsulfonyl]amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(CC(=O)N(C)C)S(=O)(=O)CCCN(C)C)C=C1 PVADCVQLBCMSHD-KTMFPKCZSA-N 0.000 description 2
- CZYSFQRFLSAAJI-QPLCGJKRSA-N ethyl (3z)-3-[[4-[[2-(dimethylamino)-2-oxoethyl]amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(NCC(=O)N(C)C)C=C1 CZYSFQRFLSAAJI-QPLCGJKRSA-N 0.000 description 2
- AZXHEJRTXWUATP-RQZHXJHFSA-N ethyl (3z)-3-[[4-[[2-(dimethylamino)acetyl]-methylamino]-3-(trifluoromethyl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CN(C)C)C(C(F)(F)F)=C1 AZXHEJRTXWUATP-RQZHXJHFSA-N 0.000 description 2
- BBAKZSSKRFAYHQ-DQSJHHFOSA-N ethyl (3z)-3-[[4-[[2-(dimethylamino)acetyl]-methylamino]-3-methoxyanilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CN(C)C)C(OC)=C1 BBAKZSSKRFAYHQ-DQSJHHFOSA-N 0.000 description 2
- VWEFBNRKWBWVSJ-RQZHXJHFSA-N ethyl (3z)-3-[[4-[[2-(dimethylamino)acetyl]-methylamino]-3-nitroanilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CN(C)C)C([N+]([O-])=O)=C1 VWEFBNRKWBWVSJ-RQZHXJHFSA-N 0.000 description 2
- INBPZZBOPABDFM-DQSJHHFOSA-N ethyl (3z)-3-[[4-[[2-[(2-amino-2-oxoethyl)-methylamino]acetyl]-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CN(C)CC(N)=O)C=C1 INBPZZBOPABDFM-DQSJHHFOSA-N 0.000 description 2
- BKKLUEPLYLXSEH-FLWNBWAVSA-N ethyl (3z)-3-[[4-[[2-[2-(dimethylamino)ethyl-methylamino]acetyl]-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CN(C)CCN(C)C)C=C1 BKKLUEPLYLXSEH-FLWNBWAVSA-N 0.000 description 2
- KOVXOBIYGAPUII-QPLCGJKRSA-N ethyl (3z)-3-[[4-[[2-aminoethyl(methyl)amino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(C)CCN)C=C1 KOVXOBIYGAPUII-QPLCGJKRSA-N 0.000 description 2
- OEHGVRVGLUGFRP-RQZHXJHFSA-N ethyl (3z)-3-[[4-[[2-methoxyethyl(methyl)amino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(C)CCOC)C=C1 OEHGVRVGLUGFRP-RQZHXJHFSA-N 0.000 description 2
- DPEATOJILBXCSZ-DQSJHHFOSA-N ethyl (3z)-3-[[4-[[[2-(dimethylamino)-2-oxoethyl]-methylamino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(C)CC(=O)N(C)C)C=C1 DPEATOJILBXCSZ-DQSJHHFOSA-N 0.000 description 2
- BLWGPVVOVJBMON-KTMFPKCZSA-N ethyl (3z)-3-[[4-[[benzyl(methyl)amino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CN(C)CC1=CC=CC=C1 BLWGPVVOVJBMON-KTMFPKCZSA-N 0.000 description 2
- JCORLWNCVJPPSB-RQZHXJHFSA-N ethyl (3z)-3-[[4-[[bis(2-hydroxyethyl)amino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(CCO)CCO)C=C1 JCORLWNCVJPPSB-RQZHXJHFSA-N 0.000 description 2
- UXSFUIUGJMZBLT-DQSJHHFOSA-N ethyl (3z)-3-[[4-[[ethyl(propyl)amino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(CN(CC)CCC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OCC)C=C2NC\1=O UXSFUIUGJMZBLT-DQSJHHFOSA-N 0.000 description 2
- QIAFNXKHWWOBRX-MVJHLKBCSA-N ethyl (3z)-3-[[4-[[methyl(2-phenylethyl)amino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CN(C)CCC1=CC=CC=C1 QIAFNXKHWWOBRX-MVJHLKBCSA-N 0.000 description 2
- IQCQBGHIMSVBKU-RQZHXJHFSA-N ethyl (3z)-3-[[4-[[methyl(propyl)amino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(CN(C)CCC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OCC)C=C2NC\1=O IQCQBGHIMSVBKU-RQZHXJHFSA-N 0.000 description 2
- FWKXTJHANITOPE-QPLCGJKRSA-N ethyl (3z)-3-[[4-[acetyl(2-aminoethyl)amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(CCN)C(C)=O)C=C1 FWKXTJHANITOPE-QPLCGJKRSA-N 0.000 description 2
- SQQLRRLMSFILOE-KTMFPKCZSA-N ethyl (3z)-3-[[4-[acetyl(2-piperidin-1-ylethyl)amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1N(C(C)=O)CCN1CCCCC1 SQQLRRLMSFILOE-KTMFPKCZSA-N 0.000 description 2
- HRZROZNKFNVLLX-IZHYLOQSSA-N ethyl (3z)-3-[[4-[acetyl(methyl)amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(C)=O)C=C1 HRZROZNKFNVLLX-IZHYLOQSSA-N 0.000 description 2
- BUYYYCZGUDSCMA-KTMFPKCZSA-N ethyl (3z)-3-[[4-[acetyl-(2-oxo-2-piperidin-1-ylethyl)amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1N(C(C)=O)CC(=O)N1CCCCC1 BUYYYCZGUDSCMA-KTMFPKCZSA-N 0.000 description 2
- ZKQOGXXXRNWYQT-DQSJHHFOSA-N ethyl (3z)-3-[[4-[acetyl-[2-(dimethylamino)ethyl]amino]-3-aminoanilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(CCN(C)C)C(C)=O)C(N)=C1 ZKQOGXXXRNWYQT-DQSJHHFOSA-N 0.000 description 2
- IJGHXPNCEXZUIU-JWGURIENSA-N ethyl (3z)-3-[[4-[acetyl-[3-(dimethylamino)propyl]amino]anilino]methylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C\NC1=CC=C(N(CCCN(C)C)C(C)=O)C=C1 IJGHXPNCEXZUIU-JWGURIENSA-N 0.000 description 2
- ORQVGHFMZJOCIR-VHXPQNKSSA-N ethyl (3z)-3-[[4-[methyl(methylcarbamoyl)amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)NC)C=C1 ORQVGHFMZJOCIR-VHXPQNKSSA-N 0.000 description 2
- BGSGVBVVBNMDGO-FLWNBWAVSA-N ethyl (3z)-3-[[4-[methyl-(2-piperidin-1-ylacetyl)amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1N(C)C(=O)CN1CCCCC1 BGSGVBVVBNMDGO-FLWNBWAVSA-N 0.000 description 2
- NWLAETZIQCOVOQ-FLWNBWAVSA-N ethyl (3z)-3-[[4-[methyl-[2-(4-methylpiperazin-1-yl)acetyl]amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1N(C)C(=O)CN1CCN(C)CC1 NWLAETZIQCOVOQ-FLWNBWAVSA-N 0.000 description 2
- SDMAVFXBWFYTCI-UHFFFAOYSA-N ethyl 2-oxo-1,3-dihydroindole-6-carboxylate Chemical compound CCOC(=O)C1=CC=C2CC(=O)NC2=C1 SDMAVFXBWFYTCI-UHFFFAOYSA-N 0.000 description 2
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group 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 description 2
- 238000009472 formulation Methods 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 description 2
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
- 230000008595 infiltration Effects 0.000 description 2
- 238000001764 infiltration Methods 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 108020004999 messenger RNA Proteins 0.000 description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
- HBHHTUPXRIAZAE-VLGSPTGOSA-N methyl (3z)-2-oxo-3-[1-[4-(2h-tetrazol-5-yl)anilino]butylidene]-1h-indole-6-carboxylate Chemical compound O=C/1NC2=CC(C(=O)OC)=CC=C2C\1=C(/CCC)NC(C=C1)=CC=C1C1=NN=NN1 HBHHTUPXRIAZAE-VLGSPTGOSA-N 0.000 description 2
- FANLPQVPAGYSFU-GYHWCHFESA-N methyl (3z)-2-oxo-3-[1-[4-(piperidin-1-ylmethyl)anilino]butylidene]-1h-indole-6-carboxylate Chemical compound O=C/1NC2=CC(C(=O)OC)=CC=C2C\1=C(/CCC)NC(C=C1)=CC=C1CN1CCCCC1 FANLPQVPAGYSFU-GYHWCHFESA-N 0.000 description 2
- JQSVEWLFMVTAGS-ZROIWOOFSA-N methyl (3z)-2-oxo-3-[[4-(2h-tetrazol-5-yl)anilino]methylidene]-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C\NC(C=C1)=CC=C1C1=NN=NN1 JQSVEWLFMVTAGS-ZROIWOOFSA-N 0.000 description 2
- FQRRZZGWVKENKU-QPLCGJKRSA-N methyl (3z)-2-oxo-3-[[4-[(3-oxopiperazin-1-yl)methyl]anilino]-phenylmethylidene]-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CN1CCNC(=O)C1 FQRRZZGWVKENKU-QPLCGJKRSA-N 0.000 description 2
- NHKGMLKDGQJHNN-QPLCGJKRSA-N methyl (3z)-2-oxo-3-[phenyl-(4-pyridin-2-ylanilino)methylidene]-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1C1=CC=CC=N1 NHKGMLKDGQJHNN-QPLCGJKRSA-N 0.000 description 2
- IQEQBXQGCPVPOO-DQSJHHFOSA-N methyl (3z)-2-oxo-3-[phenyl-[4-(2-piperidin-1-ylethyl)anilino]methylidene]-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CCN1CCCCC1 IQEQBXQGCPVPOO-DQSJHHFOSA-N 0.000 description 2
- UNEIROSAOKXQCW-MRCUWXFGSA-N methyl (3z)-2-oxo-3-[phenyl-[4-(2h-tetrazol-5-yl)anilino]methylidene]-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1C1=NN=NN1 UNEIROSAOKXQCW-MRCUWXFGSA-N 0.000 description 2
- HFTBELNGYZLFND-VHXPQNKSSA-N methyl (3z)-2-oxo-3-[phenyl-[4-(triazol-2-ylmethyl)anilino]methylidene]-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CN1N=CC=N1 HFTBELNGYZLFND-VHXPQNKSSA-N 0.000 description 2
- FTWGZBDWDBQXAG-MRCUWXFGSA-N methyl (3z)-2-oxo-3-[phenyl-[4-(trifluoromethyl)anilino]methylidene]-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(C(F)(F)F)C=C1 FTWGZBDWDBQXAG-MRCUWXFGSA-N 0.000 description 2
- IWCWQRLASYFOIU-IZHYLOQSSA-N methyl (3z)-2-oxo-3-[phenyl-[4-[(propan-2-ylamino)methyl]anilino]methylidene]-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CNC(C)C)C=C1 IWCWQRLASYFOIU-IZHYLOQSSA-N 0.000 description 2
- GCMYYSATKUWOGV-DQSJHHFOSA-N methyl (3z)-3-[(4-benzylanilino)-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CC1=CC=CC=C1 GCMYYSATKUWOGV-DQSJHHFOSA-N 0.000 description 2
- ORRNEYOVWFPWAP-MRCUWXFGSA-N methyl (3z)-3-[(4-chloroanilino)-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(Cl)C=C1 ORRNEYOVWFPWAP-MRCUWXFGSA-N 0.000 description 2
- JZQXIZWXSRTLAM-MRCUWXFGSA-N methyl (3z)-3-[(4-iodoanilino)-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(I)C=C1 JZQXIZWXSRTLAM-MRCUWXFGSA-N 0.000 description 2
- NQOXUALBKFUCJF-DQRAZIAOSA-N methyl (3z)-3-[(4-methoxyanilino)-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(OC)C=C1 NQOXUALBKFUCJF-DQRAZIAOSA-N 0.000 description 2
- ZTEXKXBNEJNPAZ-VZCXRCSSSA-N methyl (3z)-3-[1-[4-[(dimethylamino)methyl]anilino]butylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C/1NC2=CC(C(=O)OC)=CC=C2C\1=C(/CCC)NC1=CC=C(CN(C)C)C=C1 ZTEXKXBNEJNPAZ-VZCXRCSSSA-N 0.000 description 2
- AHFOHWWSQSLKQH-QOCHGBHMSA-N methyl (3z)-3-[1-[4-[[2-(dimethylamino)acetyl]-methylamino]anilino]propylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C/1NC2=CC(C(=O)OC)=CC=C2C\1=C(/CC)NC1=CC=C(N(C)C(=O)CN(C)C)C=C1 AHFOHWWSQSLKQH-QOCHGBHMSA-N 0.000 description 2
- FPCYXADPAKSIAR-BWAHOGKJSA-N methyl (3z)-3-[1-[4-[[benzyl(methyl)amino]methyl]anilino]ethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(/C)NC(C=C1)=CC=C1CN(C)CC1=CC=CC=C1 FPCYXADPAKSIAR-BWAHOGKJSA-N 0.000 description 2
- MWJRDTKUARDNNO-XHPQRKPJSA-N methyl (3z)-3-[1-[4-[[methyl(2-phenylethyl)amino]methyl]anilino]ethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(/C)NC(C=C1)=CC=C1CN(C)CCC1=CC=CC=C1 MWJRDTKUARDNNO-XHPQRKPJSA-N 0.000 description 2
- PBOIXICJADQJDW-XHPQRKPJSA-N methyl (3z)-3-[1-[4-[[methyl-[(4-methylphenyl)methyl]amino]methyl]anilino]ethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(/C)NC(C=C1)=CC=C1CN(C)CC1=CC=C(C)C=C1 PBOIXICJADQJDW-XHPQRKPJSA-N 0.000 description 2
- UTTXPPZWDJPHNM-GYHWCHFESA-N methyl (3z)-3-[1-[4-[acetyl-[3-(dimethylamino)propyl]amino]anilino]propylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C/1NC2=CC(C(=O)OC)=CC=C2C\1=C(/CC)NC1=CC=C(N(CCCN(C)C)C(C)=O)C=C1 UTTXPPZWDJPHNM-GYHWCHFESA-N 0.000 description 2
- WILZQDUBLOKSOY-VHXPQNKSSA-N methyl (3z)-3-[[3-amino-4-[(dimethylamino)methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(C)C)C(N)=C1 WILZQDUBLOKSOY-VHXPQNKSSA-N 0.000 description 2
- ATHTZBCMUSOQOK-VHXPQNKSSA-N methyl (3z)-3-[[3-bromo-4-[(dimethylamino)methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(C)C)C(Br)=C1 ATHTZBCMUSOQOK-VHXPQNKSSA-N 0.000 description 2
- HPNQZONFUXLKDA-VHXPQNKSSA-N methyl (3z)-3-[[3-chloro-4-[(dimethylamino)methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(C)C)C(Cl)=C1 HPNQZONFUXLKDA-VHXPQNKSSA-N 0.000 description 2
- ZRMIEFUAZBNBMU-QPLCGJKRSA-N methyl (3z)-3-[[3-chloro-4-[[2-(dimethylamino)acetyl]-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CN(C)C)C(Cl)=C1 ZRMIEFUAZBNBMU-QPLCGJKRSA-N 0.000 description 2
- CMEKJNNNRKFNAH-IZHYLOQSSA-N methyl (3z)-3-[[4-(1,4-diaminobutyl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(C(N)CCCN)C=C1 CMEKJNNNRKFNAH-IZHYLOQSSA-N 0.000 description 2
- IKNSSCDVQASFBP-VHXPQNKSSA-N methyl (3z)-3-[[4-(1-amino-3-hydroxypropyl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(C(N)CCO)C=C1 IKNSSCDVQASFBP-VHXPQNKSSA-N 0.000 description 2
- KFQUQGPGBSRWLL-FLWNBWAVSA-N methyl (3z)-3-[[4-(1-benzylimidazol-2-yl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1C1=NC=CN1CC1=CC=CC=C1 KFQUQGPGBSRWLL-FLWNBWAVSA-N 0.000 description 2
- BGNCLMXCLORXLK-FCQUAONHSA-N methyl (3z)-3-[[4-(1h-imidazol-2-yl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1C1=NC=CN1 BGNCLMXCLORXLK-FCQUAONHSA-N 0.000 description 2
- XXBZVVHKDMBPQL-IZHYLOQSSA-N methyl (3z)-3-[[4-(1h-imidazol-5-ylmethyl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CC1=CNC=N1 XXBZVVHKDMBPQL-IZHYLOQSSA-N 0.000 description 2
- DOOGGJTZJJJMTJ-FCQUAONHSA-N methyl (3z)-3-[[4-(2-amino-2-oxoethyl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CC(N)=O)C=C1 DOOGGJTZJJJMTJ-FCQUAONHSA-N 0.000 description 2
- YBGGVKMJPPALFD-DQRAZIAOSA-N methyl (3z)-3-[[4-(aminomethyl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN)C=C1 YBGGVKMJPPALFD-DQRAZIAOSA-N 0.000 description 2
- JYIJAYFLGBJVLP-QPLCGJKRSA-N methyl (3z)-3-[[4-(butylaminomethyl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(CNCCCC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O JYIJAYFLGBJVLP-QPLCGJKRSA-N 0.000 description 2
- YXQMTPXIYODTOH-RQZHXJHFSA-N methyl (3z)-3-[[4-(cyclohexylamino)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1NC1CCCCC1 YXQMTPXIYODTOH-RQZHXJHFSA-N 0.000 description 2
- LCAMDNGTCFSSHD-QPLCGJKRSA-N methyl (3z)-3-[[4-(diethylaminomethyl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(CN(CC)CC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O LCAMDNGTCFSSHD-QPLCGJKRSA-N 0.000 description 2
- BEULZLALWAJZNR-QPLCGJKRSA-N methyl (3z)-3-[[4-[(1,1-dioxo-1,4-thiazinan-4-yl)methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CN1CCS(=O)(=O)CC1 BEULZLALWAJZNR-QPLCGJKRSA-N 0.000 description 2
- MFMREZXKGGWAGY-FCQUAONHSA-N methyl (3z)-3-[[4-[(2,5-dioxoimidazolidin-4-yl)methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CC1NC(=O)NC1=O MFMREZXKGGWAGY-FCQUAONHSA-N 0.000 description 2
- GMJWQWHGELZQIQ-ZIADKAODSA-N methyl (3z)-3-[[4-[(3,5-dimethylpiperidin-1-yl)methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CN1CC(C)CC(C)C1 GMJWQWHGELZQIQ-ZIADKAODSA-N 0.000 description 2
- IRIFEJWVQKJYPO-RQZHXJHFSA-N methyl (3z)-3-[[4-[(4-methylpiperazin-1-yl)methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CN1CCN(C)CC1 IRIFEJWVQKJYPO-RQZHXJHFSA-N 0.000 description 2
- MZQVUAAURXIYRD-DQSJHHFOSA-N methyl (3z)-3-[[4-[(cyclohexylamino)methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CNC1CCCCC1 MZQVUAAURXIYRD-DQSJHHFOSA-N 0.000 description 2
- NJSMNIIVGXCSBI-KXYMVQBMSA-N methyl (3z)-3-[[4-[(dibenzylamino)methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CN(CC=1C=CC=CC=1)CC1=CC=CC=C1 NJSMNIIVGXCSBI-KXYMVQBMSA-N 0.000 description 2
- UDUBGBJOQMFORB-VHXPQNKSSA-N methyl (3z)-3-[[4-[(dimethylamino)methyl]-3-(trifluoromethyl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(C)C)C(C(F)(F)F)=C1 UDUBGBJOQMFORB-VHXPQNKSSA-N 0.000 description 2
- JSRRCWIQNBLGOO-QPLCGJKRSA-N methyl (3z)-3-[[4-[(dimethylamino)methyl]-3-ethoxycarbonylanilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=C(CN(C)C)C(C(=O)OCC)=CC(N\C(=C/2C3=CC=C(C=C3NC\2=O)C(=O)OC)C=2C=CC=CC=2)=C1 JSRRCWIQNBLGOO-QPLCGJKRSA-N 0.000 description 2
- AFUUYWZKISIIDQ-VHXPQNKSSA-N methyl (3z)-3-[[4-[(dimethylamino)methyl]-3-hydroxyanilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(C)C)C(O)=C1 AFUUYWZKISIIDQ-VHXPQNKSSA-N 0.000 description 2
- POJVTYBLLXHLQL-QPLCGJKRSA-N methyl (3z)-3-[[4-[1-amino-3-(dimethylamino)propyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(C(N)CCN(C)C)C=C1 POJVTYBLLXHLQL-QPLCGJKRSA-N 0.000 description 2
- ZLYZTANYDSIYPC-IZHYLOQSSA-N methyl (3z)-3-[[4-[1-amino-3-(methanesulfonamido)propyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(C(N)CCNS(C)(=O)=O)C=C1 ZLYZTANYDSIYPC-IZHYLOQSSA-N 0.000 description 2
- ZYKDYALDSSSEKC-QPLCGJKRSA-N methyl (3z)-3-[[4-[2-(1h-imidazol-5-yl)ethyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CCC1=CNC=N1 ZYKDYALDSSSEKC-QPLCGJKRSA-N 0.000 description 2
- UXPGGJLMVUQWLH-FLWNBWAVSA-N methyl (3z)-3-[[4-[2-(dimethylamino)ethyl-(pyridine-3-carbonyl)amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1N(CCN(C)C)C(=O)C1=CC=CN=C1 UXPGGJLMVUQWLH-FLWNBWAVSA-N 0.000 description 2
- WJZTXYKYCJDGGW-DQSJHHFOSA-N methyl (3z)-3-[[4-[2-(dimethylamino)ethyl-propanoylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(CCN(C)C)C(=O)CC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O WJZTXYKYCJDGGW-DQSJHHFOSA-N 0.000 description 2
- SFWYROGMRHYFHU-IZHYLOQSSA-N methyl (3z)-3-[[4-[2-(dimethylamino)ethyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CCN(C)C)C=C1 SFWYROGMRHYFHU-IZHYLOQSSA-N 0.000 description 2
- IIWXYHWYUFXQBW-VHXPQNKSSA-N methyl (3z)-3-[[4-[2-(methylamino)ethyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(CCNC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O IIWXYHWYUFXQBW-VHXPQNKSSA-N 0.000 description 2
- CXURIOROSJWAMI-QPLCGJKRSA-N methyl (3z)-3-[[4-[3-(dimethylamino)propoxy]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(OCCCN(C)C)C=C1 CXURIOROSJWAMI-QPLCGJKRSA-N 0.000 description 2
- HQVUFGHRHRIQHU-QPLCGJKRSA-N methyl (3z)-3-[[4-[3-(dimethylamino)propyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CCCN(C)C)C=C1 HQVUFGHRHRIQHU-QPLCGJKRSA-N 0.000 description 2
- QWHWQOKJBPYICM-IZHYLOQSSA-N methyl (3z)-3-[[4-[3-aminopropanoyl(methyl)amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CCN)C=C1 QWHWQOKJBPYICM-IZHYLOQSSA-N 0.000 description 2
- UTWGGRJAZSHAAZ-RQZHXJHFSA-N methyl (3z)-3-[[4-[[(2-ethoxy-2-oxoethyl)-methylamino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(CN(C)CC(=O)OCC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O UTWGGRJAZSHAAZ-RQZHXJHFSA-N 0.000 description 2
- MJBOSKJANLJEQK-DQSJHHFOSA-N methyl (3z)-3-[[4-[[2-(4-methylpiperazin-1-yl)acetyl]amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1NC(=O)CN1CCN(C)CC1 MJBOSKJANLJEQK-DQSJHHFOSA-N 0.000 description 2
- BAUFJTXWLJKPAR-DQSJHHFOSA-N methyl (3z)-3-[[4-[[2-(diethylamino)acetyl]-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(C)C(=O)CN(CC)CC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O BAUFJTXWLJKPAR-DQSJHHFOSA-N 0.000 description 2
- RXHZDTGOOZYYRM-DQSJHHFOSA-N methyl (3z)-3-[[4-[[2-(dimethylamino)-2-oxoethyl]-propanoylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(CC(=O)N(C)C)C(=O)CC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O RXHZDTGOOZYYRM-DQSJHHFOSA-N 0.000 description 2
- SLYPLUJBXFTQMT-IZHYLOQSSA-N methyl (3z)-3-[[4-[[2-(dimethylamino)-2-oxoethyl]amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(NCC(=O)N(C)C)C=C1 SLYPLUJBXFTQMT-IZHYLOQSSA-N 0.000 description 2
- HQGFACIJAOUSHR-QPLCGJKRSA-N methyl (3z)-3-[[4-[[2-(dimethylamino)acetyl]-methylamino]-3-hydroxyanilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CN(C)C)C(O)=C1 HQGFACIJAOUSHR-QPLCGJKRSA-N 0.000 description 2
- KKQAKFFHVQJBRP-RQZHXJHFSA-N methyl (3z)-3-[[4-[[2-(dimethylamino)acetyl]-methylamino]-3-methylanilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CN(C)C)C(C)=C1 KKQAKFFHVQJBRP-RQZHXJHFSA-N 0.000 description 2
- WZSPHJSIBQNMLK-QPLCGJKRSA-N methyl (3z)-3-[[4-[[2-(dimethylamino)acetyl]-methylamino]-3-nitroanilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CN(C)C)C([N+]([O-])=O)=C1 WZSPHJSIBQNMLK-QPLCGJKRSA-N 0.000 description 2
- YLNCLPUQDWLGDS-DQSJHHFOSA-N methyl (3z)-3-[[4-[[2-(dimethylamino)acetyl]-propan-2-ylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C(C)C)C(=O)CN(C)C)C=C1 YLNCLPUQDWLGDS-DQSJHHFOSA-N 0.000 description 2
- SUBBBPXDIJNZNV-DQSJHHFOSA-N methyl (3z)-3-[[4-[[2-[2-methoxyethyl(methyl)amino]acetyl]-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(C)C(=O)CN(C)CCOC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O SUBBBPXDIJNZNV-DQSJHHFOSA-N 0.000 description 2
- FKSICKKKGOVLIS-RQZHXJHFSA-N methyl (3z)-3-[[4-[[2-acetamidoethyl(methyl)amino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(C)CCNC(C)=O)C=C1 FKSICKKKGOVLIS-RQZHXJHFSA-N 0.000 description 2
- IWFYADKEUUNZOQ-QPLCGJKRSA-N methyl (3z)-3-[[4-[[3-aminopropyl(methyl)amino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(C)CCCN)C=C1 IWFYADKEUUNZOQ-QPLCGJKRSA-N 0.000 description 2
- PVDDHMABBCZBCT-DQSJHHFOSA-N methyl (3z)-3-[[4-[[4-(hydroxymethyl)piperidin-1-yl]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CN1CCC(CO)CC1 PVDDHMABBCZBCT-DQSJHHFOSA-N 0.000 description 2
- GZQQQXWKMMUNAW-DQSJHHFOSA-N methyl (3z)-3-[[4-[[bis(2-methoxyethyl)amino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(CN(CCOC)CCOC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O GZQQQXWKMMUNAW-DQSJHHFOSA-N 0.000 description 2
- RBEBGJMNWUCQSP-RQZHXJHFSA-N methyl (3z)-3-[[4-[[ethyl(propan-2-yl)amino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(CN(CC)C(C)C)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O RBEBGJMNWUCQSP-RQZHXJHFSA-N 0.000 description 2
- ZZRLBWWKZSJKMR-FLWNBWAVSA-N methyl (3z)-3-[[4-[acetyl(2-piperidin-1-ylethyl)amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1N(C(C)=O)CCN1CCCCC1 ZZRLBWWKZSJKMR-FLWNBWAVSA-N 0.000 description 2
- PWDPLHOKCYLVIC-RQZHXJHFSA-N methyl (3z)-3-[[4-[acetyl-[2-(dimethylamino)ethyl]amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(CCN(C)C)C(C)=O)C=C1 PWDPLHOKCYLVIC-RQZHXJHFSA-N 0.000 description 2
- LMDQFDUMUTWWMV-DQRAZIAOSA-N methyl (3z)-3-[[4-[carbamoyl(methyl)amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(N)=O)C=C1 LMDQFDUMUTWWMV-DQRAZIAOSA-N 0.000 description 2
- QQJODNJZFHWZML-RQZHXJHFSA-N methyl (3z)-3-[[4-[methyl(piperidine-1-carbonyl)amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1N(C)C(=O)N1CCCCC1 QQJODNJZFHWZML-RQZHXJHFSA-N 0.000 description 2
- UXGZKMOVOLAAPN-DQSJHHFOSA-N methyl (3z)-3-[[4-[methyl-[2-[methyl(propyl)amino]acetyl]amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(C)C(=O)CN(C)CCC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O UXGZKMOVOLAAPN-DQSJHHFOSA-N 0.000 description 2
- ZYGINQDWOCSBOA-UHFFFAOYSA-N methyl 1-acetyl-3-(ethoxymethylidene)-2-oxoindole-6-carboxylate Chemical compound COC(=O)C1=CC=C2C(=COCC)C(=O)N(C(C)=O)C2=C1 ZYGINQDWOCSBOA-UHFFFAOYSA-N 0.000 description 2
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- GFDYMCILCJZAAT-IZHYLOQSSA-N ethyl (3z)-3-[[3-[(dimethylamino)methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=CC(CN(C)C)=C1 GFDYMCILCJZAAT-IZHYLOQSSA-N 0.000 description 1
- GHWFWNCLIGQYCE-RQZHXJHFSA-N ethyl (3z)-3-[[3-amino-4-[[2-(dimethylamino)acetyl]-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CN(C)C)C(N)=C1 GHWFWNCLIGQYCE-RQZHXJHFSA-N 0.000 description 1
- MGHYPWDVRBOKQH-RQZHXJHFSA-N ethyl (3z)-3-[[3-bromo-4-[[2-(dimethylamino)acetyl]-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CN(C)C)C(Br)=C1 MGHYPWDVRBOKQH-RQZHXJHFSA-N 0.000 description 1
- KEUFNMADPSPXCP-QPLCGJKRSA-N ethyl (3z)-3-[[3-cyano-4-[(dimethylamino)methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(C)C)C(C#N)=C1 KEUFNMADPSPXCP-QPLCGJKRSA-N 0.000 description 1
- OCPLINVXHNEVTE-DQSJHHFOSA-N ethyl (3z)-3-[[3-cyano-4-[[2-(dimethylamino)acetyl]-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CN(C)C)C(C#N)=C1 OCPLINVXHNEVTE-DQSJHHFOSA-N 0.000 description 1
- ZPXLBJWBFHUKTE-IZHYLOQSSA-N ethyl (3z)-3-[[4-(1,3-diamino-3-oxopropyl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(C(N)CC(N)=O)C=C1 ZPXLBJWBFHUKTE-IZHYLOQSSA-N 0.000 description 1
- HMGLXPMTOJSFCU-IZHYLOQSSA-N ethyl (3z)-3-[[4-(1,3-diaminopropyl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(C(N)CCN)C=C1 HMGLXPMTOJSFCU-IZHYLOQSSA-N 0.000 description 1
- AMXWKHKQGZBFAX-QPLCGJKRSA-N ethyl (3z)-3-[[4-(1-amino-3-methoxypropyl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(C(N)CCOC)C=C1 AMXWKHKQGZBFAX-QPLCGJKRSA-N 0.000 description 1
- XIAOKDVXMUAJLG-KTMFPKCZSA-N ethyl (3z)-3-[[4-(1-benzylimidazol-2-yl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1C1=NC=CN1CC1=CC=CC=C1 XIAOKDVXMUAJLG-KTMFPKCZSA-N 0.000 description 1
- MHUTVSIFRZJXLY-VHXPQNKSSA-N ethyl (3z)-3-[[4-(1h-imidazol-2-yl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1C1=NC=CN1 MHUTVSIFRZJXLY-VHXPQNKSSA-N 0.000 description 1
- JWBWDEIPWIPTOU-QPLCGJKRSA-N ethyl (3z)-3-[[4-(1h-imidazol-5-ylmethyl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CC1=CNC=N1 JWBWDEIPWIPTOU-QPLCGJKRSA-N 0.000 description 1
- JIPGQAVXHCZNTG-QPLCGJKRSA-N ethyl (3z)-3-[[4-(2-acetamidoethyl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CCNC(C)=O)C=C1 JIPGQAVXHCZNTG-QPLCGJKRSA-N 0.000 description 1
- SIWJAQMHBDGODF-VHXPQNKSSA-N ethyl (3z)-3-[[4-(2-aminoethyl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CCN)C=C1 SIWJAQMHBDGODF-VHXPQNKSSA-N 0.000 description 1
- BBQOMPAPYHAMFE-DQSJHHFOSA-N ethyl (3z)-3-[[4-(3,6-dihydro-2h-pyridin-1-ylmethyl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CN1CCC=CC1 BBQOMPAPYHAMFE-DQSJHHFOSA-N 0.000 description 1
- MQSZSNUWQIYNCH-RQZHXJHFSA-N ethyl (3z)-3-[[4-(3-acetamido-1-aminopropyl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(C(N)CCNC(C)=O)C=C1 MQSZSNUWQIYNCH-RQZHXJHFSA-N 0.000 description 1
- WRCVXBONRYXYEO-IZHYLOQSSA-N ethyl (3z)-3-[[4-(3-amino-3-oxopropyl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CCC(N)=O)C=C1 WRCVXBONRYXYEO-IZHYLOQSSA-N 0.000 description 1
- FQMATBWTWBJSPO-ZIADKAODSA-N ethyl (3z)-3-[[4-(anilinomethyl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CNC1=CC=CC=C1 FQMATBWTWBJSPO-ZIADKAODSA-N 0.000 description 1
- BOCNHONOUCJBRT-DQSJHHFOSA-N ethyl (3z)-3-[[4-(cyclohexanecarbonyl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1C(=O)C1CCCCC1 BOCNHONOUCJBRT-DQSJHHFOSA-N 0.000 description 1
- QHUDIXGJTODSBM-DQSJHHFOSA-N ethyl (3z)-3-[[4-(cyclohexylamino)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1NC1CCCCC1 QHUDIXGJTODSBM-DQSJHHFOSA-N 0.000 description 1
- HZMZQDBQQMLTGJ-RQZHXJHFSA-N ethyl (3z)-3-[[4-[(1,1-dioxo-1,4-thiazinan-4-yl)methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CN1CCS(=O)(=O)CC1 HZMZQDBQQMLTGJ-RQZHXJHFSA-N 0.000 description 1
- ZINNDPFIXNMKJZ-MBELHXAFSA-N ethyl (3z)-3-[[4-[(2,5-dioxoimidazolidin-4-ylidene)methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1C=C1NC(=O)NC1=O ZINNDPFIXNMKJZ-MBELHXAFSA-N 0.000 description 1
- MUAUVCXWMHWZHJ-FLWNBWAVSA-N ethyl (3z)-3-[[4-[(2,6-dimethylpiperidin-1-yl)methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CN1C(C)CCCC1C MUAUVCXWMHWZHJ-FLWNBWAVSA-N 0.000 description 1
- MICVHMMKZHTUAB-RQZHXJHFSA-N ethyl (3z)-3-[[4-[(2-methylpropylamino)methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CNCC(C)C)C=C1 MICVHMMKZHTUAB-RQZHXJHFSA-N 0.000 description 1
- AGRUGIBTTDRWNM-RQZHXJHFSA-N ethyl (3z)-3-[[4-[(3-hydroxypyrrolidin-1-yl)methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CN1CCC(O)C1 AGRUGIBTTDRWNM-RQZHXJHFSA-N 0.000 description 1
- JNFMCZHQSYIZKU-ZIADKAODSA-N ethyl (3z)-3-[[4-[(4-methoxypiperidin-1-yl)methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CN1CCC(OC)CC1 JNFMCZHQSYIZKU-ZIADKAODSA-N 0.000 description 1
- NWHXMHYMDFNAOQ-FCQUAONHSA-N ethyl (3z)-3-[[4-[(diaminomethylideneamino)methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CNC(N)=N)C=C1 NWHXMHYMDFNAOQ-FCQUAONHSA-N 0.000 description 1
- PDUQRDIYTOIXCO-RQZHXJHFSA-N ethyl (3z)-3-[[4-[(dimethylamino)methyl]-3-ethoxycarbonylanilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(C)C)C(C(=O)OCC)=C1 PDUQRDIYTOIXCO-RQZHXJHFSA-N 0.000 description 1
- PXEKBKUCLHQUIM-IZHYLOQSSA-N ethyl (3z)-3-[[4-[(dimethylamino)methyl]-3-fluoroanilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(C)C)C(F)=C1 PXEKBKUCLHQUIM-IZHYLOQSSA-N 0.000 description 1
- YOWHTRAZMMBOBZ-QPLCGJKRSA-N ethyl (3z)-3-[[4-[(dimethylamino)methyl]-3-methylanilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(C)C)C(C)=C1 YOWHTRAZMMBOBZ-QPLCGJKRSA-N 0.000 description 1
- FZYJUDWSHZQXIT-IZHYLOQSSA-N ethyl (3z)-3-[[4-[(dimethylamino)methyl]-3-nitroanilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(C)C)C([N+]([O-])=O)=C1 FZYJUDWSHZQXIT-IZHYLOQSSA-N 0.000 description 1
- RDJCTPHXBBUOOS-PDGQHHTCSA-N ethyl (3z)-3-[[4-[(dimethylamino)methyl]anilino]methylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C\NC1=CC=C(CN(C)C)C=C1 RDJCTPHXBBUOOS-PDGQHHTCSA-N 0.000 description 1
- MYWHXBKARBNDFR-RQZHXJHFSA-N ethyl (3z)-3-[[4-[1-amino-3-(dimethylamino)propyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(C(N)CCN(C)C)C=C1 MYWHXBKARBNDFR-RQZHXJHFSA-N 0.000 description 1
- UHKVEGYQVGJASB-ZIADKAODSA-N ethyl (3z)-3-[[4-[2-(4-hydroxypiperidin-1-yl)ethyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CCN1CCC(O)CC1 UHKVEGYQVGJASB-ZIADKAODSA-N 0.000 description 1
- LUAOJMVTEOCKNH-ZIADKAODSA-N ethyl (3z)-3-[[4-[2-(diethylamino)ethyl-methylsulfonylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(CCN(CC)CC)S(C)(=O)=O)C=C1 LUAOJMVTEOCKNH-ZIADKAODSA-N 0.000 description 1
- PCYHTTAQBUQYEM-DQSJHHFOSA-N ethyl (3z)-3-[[4-[2-(diethylamino)ethyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CCN(CC)CC)C=C1 PCYHTTAQBUQYEM-DQSJHHFOSA-N 0.000 description 1
- KMSWNGUOBCAPQD-ZIADKAODSA-N ethyl (3z)-3-[[4-[2-(dimethylamino)ethyl-(2-methylpropanoyl)amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(CCN(C)C)C(=O)C(C)C)C=C1 KMSWNGUOBCAPQD-ZIADKAODSA-N 0.000 description 1
- BKWXEEZBTJQHOJ-FLWNBWAVSA-N ethyl (3z)-3-[[4-[2-(dimethylamino)ethyl-(furan-2-carbonyl)amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1N(CCN(C)C)C(=O)C1=CC=CO1 BKWXEEZBTJQHOJ-FLWNBWAVSA-N 0.000 description 1
- PVTLYGHJNKTUNG-QPLCGJKRSA-N ethyl (3z)-3-[[4-[2-(dimethylamino)ethyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CCN(C)C)C=C1 PVTLYGHJNKTUNG-QPLCGJKRSA-N 0.000 description 1
- ZXPFMRZTJDKPPB-FLWNBWAVSA-N ethyl (3z)-3-[[4-[2-(dimethylamino)ethylsulfonyl-[2-(dimethylamino)-2-oxoethyl]amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(CC(=O)N(C)C)S(=O)(=O)CCN(C)C)C=C1 ZXPFMRZTJDKPPB-FLWNBWAVSA-N 0.000 description 1
- OLQAKCNOBMBIPU-VHXPQNKSSA-N ethyl (3z)-3-[[4-[2-amino-1-(methylamino)-1-oxopropan-2-yl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(C(C)(N)C(=O)NC)C=C1 OLQAKCNOBMBIPU-VHXPQNKSSA-N 0.000 description 1
- FMXKUPDDYNBPBY-FLWNBWAVSA-N ethyl (3z)-3-[[4-[3-(diethylamino)propanoyl-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CCN(CC)CC)C=C1 FMXKUPDDYNBPBY-FLWNBWAVSA-N 0.000 description 1
- YDUZAKOFNDZPOK-RQZHXJHFSA-N ethyl (3z)-3-[[4-[3-(dimethylamino)propoxy]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(OCCCN(C)C)C=C1 YDUZAKOFNDZPOK-RQZHXJHFSA-N 0.000 description 1
- OKYBZVUDULWEDR-DQSJHHFOSA-N ethyl (3z)-3-[[4-[3-(dimethylamino)propyl-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)CCCN(C)C)C=C1 OKYBZVUDULWEDR-DQSJHHFOSA-N 0.000 description 1
- JENJPFAMUXIZRO-QPLCGJKRSA-N ethyl (3z)-3-[[4-[3-aminopropanoyl(methyl)amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CCN)C=C1 JENJPFAMUXIZRO-QPLCGJKRSA-N 0.000 description 1
- LPDUXWXQCAKPHG-KXYMVQBMSA-N ethyl (3z)-3-[[4-[[2-(4-benzylpiperazin-1-yl)acetyl]-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1N(C)C(=O)CN(CC1)CCN1CC1=CC=CC=C1 LPDUXWXQCAKPHG-KXYMVQBMSA-N 0.000 description 1
- IYXOUZAMPLPPHJ-ZIADKAODSA-N ethyl (3z)-3-[[4-[[2-(diethylamino)acetyl]-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CN(CC)CC)C=C1 IYXOUZAMPLPPHJ-ZIADKAODSA-N 0.000 description 1
- XREDDDJIQONGFW-ZIADKAODSA-N ethyl (3z)-3-[[4-[[2-(dimethylamino)-2-oxoethyl]-propanoylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(CC(=O)N(C)C)C(=O)CC)C=C1 XREDDDJIQONGFW-ZIADKAODSA-N 0.000 description 1
- HULZDJAALCAJIO-RQZHXJHFSA-N ethyl (3z)-3-[[4-[[2-(dimethylamino)acetyl]-methylamino]-3-hydroxyanilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CN(C)C)C(O)=C1 HULZDJAALCAJIO-RQZHXJHFSA-N 0.000 description 1
- CSTUFJRYCMQQQM-DQSJHHFOSA-N ethyl (3z)-3-[[4-[[2-(dimethylamino)acetyl]-methylamino]-3-methylanilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CN(C)C)C(C)=C1 CSTUFJRYCMQQQM-DQSJHHFOSA-N 0.000 description 1
- RXSMTEABPKZJSU-UYRXBGFRSA-N ethyl (3z)-3-[[4-[[2-(dimethylamino)acetyl]-methylamino]anilino]methylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C\NC1=CC=C(N(C)C(=O)CN(C)C)C=C1 RXSMTEABPKZJSU-UYRXBGFRSA-N 0.000 description 1
- KLGREXUHOWSUCI-ZIADKAODSA-N ethyl (3z)-3-[[4-[[2-(dimethylamino)acetyl]-propan-2-ylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C(C)C)C(=O)CN(C)C)C=C1 KLGREXUHOWSUCI-ZIADKAODSA-N 0.000 description 1
- XETGZBDAWRWVNO-DQSJHHFOSA-N ethyl (3z)-3-[[4-[[2-(dimethylamino)ethyl-methylamino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(C)CCN(C)C)C=C1 XETGZBDAWRWVNO-DQSJHHFOSA-N 0.000 description 1
- QOPFVEUTNDXQNA-RQZHXJHFSA-N ethyl (3z)-3-[[4-[[2-(ethylamino)acetyl]-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(C)C(=O)CNCC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OCC)C=C2NC\1=O QOPFVEUTNDXQNA-RQZHXJHFSA-N 0.000 description 1
- VUWZNUSAPAMEIA-RQZHXJHFSA-N ethyl (3z)-3-[[4-[[2-(methanesulfonamido)ethyl-methylamino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(C)CCNS(C)(=O)=O)C=C1 VUWZNUSAPAMEIA-RQZHXJHFSA-N 0.000 description 1
- VCSOYTCDZBZUNQ-ZIADKAODSA-N ethyl (3z)-3-[[4-[[2-[2-methoxyethyl(methyl)amino]acetyl]-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CN(C)CCOC)C=C1 VCSOYTCDZBZUNQ-ZIADKAODSA-N 0.000 description 1
- PQXYOHYGEUOJQM-ZIADKAODSA-N ethyl (3z)-3-[[4-[[2-amino-4-methoxy-2-(2-methoxyethyl)butanoyl]-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)C(N)(CCOC)CCOC)C=C1 PQXYOHYGEUOJQM-ZIADKAODSA-N 0.000 description 1
- GKLZWJVAGURZJE-ZIADKAODSA-N ethyl (3z)-3-[[4-[[3-(dimethylamino)propyl-methylamino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(C)CCCN(C)C)C=C1 GKLZWJVAGURZJE-ZIADKAODSA-N 0.000 description 1
- YDWTZPKQPNXBBU-ZIADKAODSA-N ethyl (3z)-3-[[4-[[3-acetamidopropyl(methyl)amino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(C)CCCNC(C)=O)C=C1 YDWTZPKQPNXBBU-ZIADKAODSA-N 0.000 description 1
- UZPJPADJORIKJY-MVJHLKBCSA-N ethyl (3z)-3-[[4-[[benzyl(ethyl)amino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CN(CC)CC1=CC=CC=C1 UZPJPADJORIKJY-MVJHLKBCSA-N 0.000 description 1
- MJUKTKWSJVXXJB-ZIADKAODSA-N ethyl (3z)-3-[[4-[[bis(2-methoxyethyl)amino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(CCOC)CCOC)C=C1 MJUKTKWSJVXXJB-ZIADKAODSA-N 0.000 description 1
- JYYWESFIVPZCFS-QPLCGJKRSA-N ethyl (3z)-3-[[4-[[ethyl(methyl)amino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(C)CC)C=C1 JYYWESFIVPZCFS-QPLCGJKRSA-N 0.000 description 1
- MZGWTSGORKZGJA-RQZHXJHFSA-N ethyl (3z)-3-[[4-[[methyl(propan-2-yl)amino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(C)C(C)C)C=C1 MZGWTSGORKZGJA-RQZHXJHFSA-N 0.000 description 1
- HBRJGBCAONZVFS-RQZHXJHFSA-N ethyl (3z)-3-[[4-[[methyl-[2-(methylamino)-2-oxoethyl]amino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(C)CC(=O)NC)C=C1 HBRJGBCAONZVFS-RQZHXJHFSA-N 0.000 description 1
- XGSUJNSWUXJDLL-QPLCGJKRSA-N ethyl (3z)-3-[[4-[acetyl-(2-amino-2-oxoethyl)amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(CC(N)=O)C(C)=O)C=C1 XGSUJNSWUXJDLL-QPLCGJKRSA-N 0.000 description 1
- GKGRWAJQMYQSRS-DQSJHHFOSA-N ethyl (3z)-3-[[4-[acetyl-[2-(dimethylamino)-2-oxoethyl]amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(CC(=O)N(C)C)C(C)=O)C=C1 GKGRWAJQMYQSRS-DQSJHHFOSA-N 0.000 description 1
- BGMXTAOGVWVFPK-DQSJHHFOSA-N ethyl (3z)-3-[[4-[acetyl-[2-(dimethylamino)ethyl]amino]-3-bromoanilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(CCN(C)C)C(C)=O)C(Br)=C1 BGMXTAOGVWVFPK-DQSJHHFOSA-N 0.000 description 1
- LXBWKJBJJPXMMQ-DQSJHHFOSA-N ethyl (3z)-3-[[4-[acetyl-[2-(methylamino)propyl]amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(CC(C)NC)C(C)=O)C=C1 LXBWKJBJJPXMMQ-DQSJHHFOSA-N 0.000 description 1
- NETCICHFVHZSSG-ZIADKAODSA-N ethyl (3z)-3-[[4-[acetyl-[3-(dimethylamino)propyl]amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(CCCN(C)C)C(C)=O)C=C1 NETCICHFVHZSSG-ZIADKAODSA-N 0.000 description 1
- FMOOGDDUNYSNGV-MVJHLKBCSA-N ethyl (3z)-3-[[4-[benzoyl-[2-(dimethylamino)ethyl]amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1N(CCN(C)C)C(=O)C1=CC=CC=C1 FMOOGDDUNYSNGV-MVJHLKBCSA-N 0.000 description 1
- TYKDBECUAULTFY-KARKAFJISA-N ethyl (3z)-3-[[4-[benzyl-[2-(dimethylamino)acetyl]amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1N(C(=O)CN(C)C)CC1=CC=CC=C1 TYKDBECUAULTFY-KARKAFJISA-N 0.000 description 1
- GVQOVWDLYNTVOA-IZHYLOQSSA-N ethyl (3z)-3-[[4-[cyanomethyl(methylsulfonyl)amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(CC#N)S(C)(=O)=O)C=C1 GVQOVWDLYNTVOA-IZHYLOQSSA-N 0.000 description 1
- NPMGCBPWXXVSJG-DQSJHHFOSA-N ethyl (3z)-3-[[4-[methyl(piperidine-1-carbonyl)amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1N(C)C(=O)N1CCCCC1 NPMGCBPWXXVSJG-DQSJHHFOSA-N 0.000 description 1
- RKZAUAWSYBJYGG-RQZHXJHFSA-N ethyl (3z)-3-[[4-[methyl-[3-(methylamino)propanoyl]amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CCNC)C=C1 RKZAUAWSYBJYGG-RQZHXJHFSA-N 0.000 description 1
- TYKFNHWOUWEJIB-DQRAZIAOSA-N ethyl (3z)-3-[[methyl(piperidin-4-yl)amino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\N(C)C1CCNCC1 TYKFNHWOUWEJIB-DQRAZIAOSA-N 0.000 description 1
- RDEMCYZJUBPCMK-DQRAZIAOSA-N ethyl (3z)-3-[anilino(phenyl)methylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=CC=C1 RDEMCYZJUBPCMK-DQRAZIAOSA-N 0.000 description 1
- WWTYMHANUAWVMT-DQRAZIAOSA-N ethyl 4-[[(z)-(6-carbamoyl-2-oxo-1h-indol-3-ylidene)-phenylmethyl]amino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(N)=O)C=C2NC\1=O WWTYMHANUAWVMT-DQRAZIAOSA-N 0.000 description 1
- 229940093499 ethyl acetate Drugs 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 229960002714 fluticasone Drugs 0.000 description 1
- MGNNYOODZCAHBA-GQKYHHCASA-N fluticasone Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)SCF)(O)[C@@]2(C)C[C@@H]1O MGNNYOODZCAHBA-GQKYHHCASA-N 0.000 description 1
- OATDVDIMNNZTEY-DAXLTYESSA-N flutropium Chemical class C[N@@+]1(CCF)[C@H]2CC[C@@H]1C[C@@H](C2)OC(=O)C(O)(C1=CC=CC=C1)C1=CC=CC=C1 OATDVDIMNNZTEY-DAXLTYESSA-N 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 235000001727 glucose Nutrition 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229940076085 gold Drugs 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 229940116364 hard fat Drugs 0.000 description 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 1
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005935 hexyloxycarbonyl group Chemical group 0.000 description 1
- 210000005260 human cell Anatomy 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- OEXHQOGQTVQTAT-JRNQLAHRSA-N ipratropium Chemical class O([C@H]1C[C@H]2CC[C@@H](C1)[N@@+]2(C)C(C)C)C(=O)C(CO)C1=CC=CC=C1 OEXHQOGQTVQTAT-JRNQLAHRSA-N 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 208000017169 kidney disease Diseases 0.000 description 1
- 229950005286 lanepitant Drugs 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000010841 mRNA extraction Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- FRRZVDUVJQJQAY-ICFOKQHNSA-N methyl (3z)-2-oxo-3-[1-[4-(2h-tetrazol-5-yl)anilino]propylidene]-1h-indole-6-carboxylate Chemical compound O=C/1NC2=CC(C(=O)OC)=CC=C2C\1=C(/CC)NC(C=C1)=CC=C1C1=NN=NN1 FRRZVDUVJQJQAY-ICFOKQHNSA-N 0.000 description 1
- WNHGOWCEZGPKCM-JWGURIENSA-N methyl (3z)-2-oxo-3-[1-[4-(piperidin-1-ylmethyl)anilino]ethylidene]-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(/C)NC(C=C1)=CC=C1CN1CCCCC1 WNHGOWCEZGPKCM-JWGURIENSA-N 0.000 description 1
- MILPOVQHFLFZLJ-LNVKXUELSA-N methyl (3z)-2-oxo-3-[1-[4-(piperidin-1-ylmethyl)anilino]propylidene]-1h-indole-6-carboxylate Chemical compound O=C/1NC2=CC(C(=O)OC)=CC=C2C\1=C(/CC)NC(C=C1)=CC=C1CN1CCCCC1 MILPOVQHFLFZLJ-LNVKXUELSA-N 0.000 description 1
- KHEQXLHVUPKNQU-QPLCGJKRSA-N methyl (3z)-2-oxo-3-[[4-[(1-oxo-1,4-thiazinan-4-yl)methyl]anilino]-phenylmethylidene]-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CN1CCS(=O)CC1 KHEQXLHVUPKNQU-QPLCGJKRSA-N 0.000 description 1
- QDSBLMNXFRUSAC-QPLCGJKRSA-N methyl (3z)-2-oxo-3-[phenyl-(4-pyridin-3-ylanilino)methylidene]-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1C1=CC=CN=C1 QDSBLMNXFRUSAC-QPLCGJKRSA-N 0.000 description 1
- CRAUMZAXRDXPMY-QPLCGJKRSA-N methyl (3z)-2-oxo-3-[phenyl-[4-(piperazin-1-ylmethyl)anilino]methylidene]-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CN1CCNCC1 CRAUMZAXRDXPMY-QPLCGJKRSA-N 0.000 description 1
- PJYLAPUQQYSUKA-RQZHXJHFSA-N methyl (3z)-2-oxo-3-[phenyl-[4-(piperidin-1-ylmethyl)anilino]methylidene]-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CN1CCCCC1 PJYLAPUQQYSUKA-RQZHXJHFSA-N 0.000 description 1
- WFWFAKWTVKMAJE-IZHYLOQSSA-N methyl (3z)-2-oxo-3-[phenyl-[4-(propylaminomethyl)anilino]methylidene]-1h-indole-6-carboxylate Chemical compound C1=CC(CNCCC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O WFWFAKWTVKMAJE-IZHYLOQSSA-N 0.000 description 1
- IYORXXKXXWXNMT-QPLCGJKRSA-N methyl (3z)-2-oxo-3-[phenyl-[4-(thiomorpholin-4-ylmethyl)anilino]methylidene]-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CN1CCSCC1 IYORXXKXXWXNMT-QPLCGJKRSA-N 0.000 description 1
- PVQLMANNFBZOFB-MRCUWXFGSA-N methyl (3z)-3-[(4-bromoanilino)-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(Br)C=C1 PVQLMANNFBZOFB-MRCUWXFGSA-N 0.000 description 1
- OHCAWFMXYUNPGZ-FCQUAONHSA-N methyl (3z)-3-[(4-ethoxyanilino)-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(OCC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O OHCAWFMXYUNPGZ-FCQUAONHSA-N 0.000 description 1
- WLLXCGQUQRIENQ-MRCUWXFGSA-N methyl (3z)-3-[(4-fluoroanilino)-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(F)C=C1 WLLXCGQUQRIENQ-MRCUWXFGSA-N 0.000 description 1
- GCMIRJPAFHPSCD-DQRAZIAOSA-N methyl (3z)-3-[(4-methylanilino)-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(C)C=C1 GCMIRJPAFHPSCD-DQRAZIAOSA-N 0.000 description 1
- UQAMDWYLNNWLHK-MRCUWXFGSA-N methyl (3z)-3-[(4-nitroanilino)-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C([N+]([O-])=O)C=C1 UQAMDWYLNNWLHK-MRCUWXFGSA-N 0.000 description 1
- ICKHFDKFBSISCK-ZZEZOPTASA-N methyl (3z)-3-[1-[4-[(dimethylamino)methyl]anilino]propylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C/1NC2=CC(C(=O)OC)=CC=C2C\1=C(/CC)NC1=CC=C(CN(C)C)C=C1 ICKHFDKFBSISCK-ZZEZOPTASA-N 0.000 description 1
- KUUMFIARCJBLGC-QQXSKIMKSA-N methyl (3z)-3-[1-[4-[2-(1,3-benzodioxol-5-yl)-1-(methylamino)ethyl]anilino]ethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C\1NC2=CC(C(=O)OC)=CC=C2C/1=C(C)/NC(C=C1)=CC=C1C(NC)CC1=CC=C(OCO2)C2=C1 KUUMFIARCJBLGC-QQXSKIMKSA-N 0.000 description 1
- CFFRNFLDXCTESN-UQQQWYQISA-N methyl (3z)-3-[1-[4-[[(4-bromophenyl)methyl-methylamino]methyl]anilino]ethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(/C)NC(C=C1)=CC=C1CN(C)CC1=CC=C(Br)C=C1 CFFRNFLDXCTESN-UQQQWYQISA-N 0.000 description 1
- IXOHHHGFPNGORW-UQQQWYQISA-N methyl (3z)-3-[1-[4-[[(4-chlorophenyl)methyl-methylamino]methyl]anilino]ethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(/C)NC(C=C1)=CC=C1CN(C)CC1=CC=C(Cl)C=C1 IXOHHHGFPNGORW-UQQQWYQISA-N 0.000 description 1
- UKDNXXZAGVDGLC-ATJXCDBQSA-N methyl (3z)-3-[1-[4-[[2-(dimethylamino)acetyl]-methylamino]anilino]butylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C/1NC2=CC(C(=O)OC)=CC=C2C\1=C(/CCC)NC1=CC=C(N(C)C(=O)CN(C)C)C=C1 UKDNXXZAGVDGLC-ATJXCDBQSA-N 0.000 description 1
- VAHWEVGCUFXVQK-STZFKDTASA-N methyl (3z)-3-[1-[4-[[2-(dimethylamino)acetyl]-methylamino]anilino]ethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(/C)NC1=CC=C(N(C)C(=O)CN(C)C)C=C1 VAHWEVGCUFXVQK-STZFKDTASA-N 0.000 description 1
- OOEHKUUOXWVMEJ-BZZOAKBMSA-N methyl (3z)-3-[1-[4-[acetyl-[3-(dimethylamino)propyl]amino]anilino]butylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C/1NC2=CC(C(=O)OC)=CC=C2C\1=C(/CCC)NC1=CC=C(N(CCCN(C)C)C(C)=O)C=C1 OOEHKUUOXWVMEJ-BZZOAKBMSA-N 0.000 description 1
- PSBOWDCVRMIKJN-KQWNVCNZSA-N methyl (3z)-3-[1-[4-[acetyl-[3-(dimethylamino)propyl]amino]anilino]ethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(/C)NC1=CC=C(N(CCCN(C)C)C(C)=O)C=C1 PSBOWDCVRMIKJN-KQWNVCNZSA-N 0.000 description 1
- VTXODFQTVCCEPN-FLWNBWAVSA-N methyl (3z)-3-[[2,3-dimethyl-4-[[2-(4-methylpiperazin-1-yl)acetyl]amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C(=C1C)C)=CC=C1NC(=O)CN1CCN(C)CC1 VTXODFQTVCCEPN-FLWNBWAVSA-N 0.000 description 1
- UYRMFXGNPAOJJM-VHXPQNKSSA-N methyl (3z)-3-[[3,5-dichloro-4-[(dimethylamino)methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC(Cl)=C(CN(C)C)C(Cl)=C1 UYRMFXGNPAOJJM-VHXPQNKSSA-N 0.000 description 1
- MBVRUWVWDCNEDU-IZHYLOQSSA-N methyl (3z)-3-[[3,5-dichloro-4-[[2-(dimethylamino)acetyl]-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC(Cl)=C(N(C)C(=O)CN(C)C)C(Cl)=C1 MBVRUWVWDCNEDU-IZHYLOQSSA-N 0.000 description 1
- FRGWKIYCYQXJCM-QPLCGJKRSA-N methyl (3z)-3-[[3-acetamido-4-[(dimethylamino)methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(C)C)C(NC(C)=O)=C1 FRGWKIYCYQXJCM-QPLCGJKRSA-N 0.000 description 1
- ZIZPEFXDEIOUEY-QPLCGJKRSA-N methyl (3z)-3-[[3-amino-4-[[2-(dimethylamino)acetyl]-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CN(C)C)C(N)=C1 ZIZPEFXDEIOUEY-QPLCGJKRSA-N 0.000 description 1
- MDHPVJCMQBSWTC-QPLCGJKRSA-N methyl (3z)-3-[[3-bromo-4-[[2-(dimethylamino)acetyl]-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CN(C)C)C(Br)=C1 MDHPVJCMQBSWTC-QPLCGJKRSA-N 0.000 description 1
- VNEYRWIVXKQUBH-VHXPQNKSSA-N methyl (3z)-3-[[3-carbamoyl-4-[(dimethylamino)methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(C)C)C(C(N)=O)=C1 VNEYRWIVXKQUBH-VHXPQNKSSA-N 0.000 description 1
- XIAJYIFWQFOATP-QPLCGJKRSA-N methyl (3z)-3-[[3-carbamoyl-4-[[2-(dimethylamino)acetyl]-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CN(C)C)C(C(N)=O)=C1 XIAJYIFWQFOATP-QPLCGJKRSA-N 0.000 description 1
- YNWNLKOJWLJXLT-IZHYLOQSSA-N methyl (3z)-3-[[3-cyano-4-[(dimethylamino)methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(C)C)C(C#N)=C1 YNWNLKOJWLJXLT-IZHYLOQSSA-N 0.000 description 1
- LITNYBZNPBBUDL-RQZHXJHFSA-N methyl (3z)-3-[[3-cyano-4-[[2-(dimethylamino)acetyl]-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CN(C)C)C(C#N)=C1 LITNYBZNPBBUDL-RQZHXJHFSA-N 0.000 description 1
- CSMAMMGWSPPCFM-VHXPQNKSSA-N methyl (3z)-3-[[4-(1,3-diaminopropyl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(C(N)CCN)C=C1 CSMAMMGWSPPCFM-VHXPQNKSSA-N 0.000 description 1
- BRESLQOHIMDFJC-FCQUAONHSA-N methyl (3z)-3-[[4-(2-aminoethyl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CCN)C=C1 BRESLQOHIMDFJC-FCQUAONHSA-N 0.000 description 1
- WYPKJAANQARQNV-RQZHXJHFSA-N methyl (3z)-3-[[4-(3,6-dihydro-2h-pyridin-1-ylmethyl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CN1CCC=CC1 WYPKJAANQARQNV-RQZHXJHFSA-N 0.000 description 1
- UKZBPRXAASHSDP-VHXPQNKSSA-N methyl (3z)-3-[[4-(3-amino-3-oxopropyl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CCC(N)=O)C=C1 UKZBPRXAASHSDP-VHXPQNKSSA-N 0.000 description 1
- YKZFJSOJAKUINN-VHXPQNKSSA-N methyl (3z)-3-[[4-(3-aminopropyl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CCCN)C=C1 YKZFJSOJAKUINN-VHXPQNKSSA-N 0.000 description 1
- ZRVRRMHTQYERBN-RQZHXJHFSA-N methyl (3z)-3-[[4-(4-acetamido-1-aminobutyl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(C(N)CCCNC(C)=O)C=C1 ZRVRRMHTQYERBN-RQZHXJHFSA-N 0.000 description 1
- OKBAJDUJXQITPZ-BZZOAKBMSA-N methyl (3z)-3-[[4-(5-methyl-1h-imidazol-4-yl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1C=1N=CNC=1C OKBAJDUJXQITPZ-BZZOAKBMSA-N 0.000 description 1
- XWJDCUCFMSIPPA-RQZHXJHFSA-N methyl (3z)-3-[[4-(cyclohexanecarbonyl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1C(=O)C1CCCCC1 XWJDCUCFMSIPPA-RQZHXJHFSA-N 0.000 description 1
- DCKKKQXINVKTJL-DQSJHHFOSA-N methyl (3z)-3-[[4-(cyclohexylidenemethyl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1C=C1CCCCC1 DCKKKQXINVKTJL-DQSJHHFOSA-N 0.000 description 1
- GUSPUPJKTCNHOJ-VHXPQNKSSA-N methyl (3z)-3-[[4-(ethylaminomethyl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(CNCC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O GUSPUPJKTCNHOJ-VHXPQNKSSA-N 0.000 description 1
- AZLHTYINGAUYFA-FCQUAONHSA-N methyl (3z)-3-[[4-(methylaminomethyl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(CNC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O AZLHTYINGAUYFA-FCQUAONHSA-N 0.000 description 1
- IDWZQYHNNILFMO-QPLCGJKRSA-N methyl (3z)-3-[[4-(morpholin-4-ylmethyl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CN1CCOCC1 IDWZQYHNNILFMO-QPLCGJKRSA-N 0.000 description 1
- URNUEBLYEXQFTO-WVVAYPLRSA-N methyl (3z)-3-[[4-[(2,5-dioxoimidazolidin-4-ylidene)methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1C=C1NC(=O)NC1=O URNUEBLYEXQFTO-WVVAYPLRSA-N 0.000 description 1
- YMIMFEBACPQKJI-QPLCGJKRSA-N methyl (3z)-3-[[4-[(2-acetamidoacetyl)-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CNC(C)=O)C=C1 YMIMFEBACPQKJI-QPLCGJKRSA-N 0.000 description 1
- SEZYXLIMGCZJMT-VHXPQNKSSA-N methyl (3z)-3-[[4-[(2-amino-2-oxoethyl)-methylsulfonylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(CC(N)=O)S(C)(=O)=O)C=C1 SEZYXLIMGCZJMT-VHXPQNKSSA-N 0.000 description 1
- FTERNYMEXWLTAM-RQZHXJHFSA-N methyl (3z)-3-[[4-[(2-imidazol-1-ylacetyl)-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1N(C)C(=O)CN1C=CN=C1 FTERNYMEXWLTAM-RQZHXJHFSA-N 0.000 description 1
- FTJZNXYBEQOVKI-QPLCGJKRSA-N methyl (3z)-3-[[4-[(2-methylpropylamino)methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CNCC(C)C)C=C1 FTJZNXYBEQOVKI-QPLCGJKRSA-N 0.000 description 1
- HMDBPOYXPOSDJX-DQSJHHFOSA-N methyl (3z)-3-[[4-[(4-methoxypiperidin-1-yl)methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1CC(OC)CCN1CC(C=C1)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O HMDBPOYXPOSDJX-DQSJHHFOSA-N 0.000 description 1
- VLVSTMQEIKJUIB-ZIADKAODSA-N methyl (3z)-3-[[4-[(benzylamino)methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CNCC1=CC=CC=C1 VLVSTMQEIKJUIB-ZIADKAODSA-N 0.000 description 1
- YPCCPYTWELSUPO-IZHYLOQSSA-N methyl (3z)-3-[[4-[(dimethylamino)methyl]-3-(methanesulfonamido)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(C)C)C(NS(C)(=O)=O)=C1 YPCCPYTWELSUPO-IZHYLOQSSA-N 0.000 description 1
- QXMDRRDVEIGIAL-VHXPQNKSSA-N methyl (3z)-3-[[4-[(dimethylamino)methyl]-3-fluoroanilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(C)C)C(F)=C1 QXMDRRDVEIGIAL-VHXPQNKSSA-N 0.000 description 1
- AZKWUVWJDOGUBW-IZHYLOQSSA-N methyl (3z)-3-[[4-[(dimethylamino)methyl]-3-methoxyanilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(C)C)C(OC)=C1 AZKWUVWJDOGUBW-IZHYLOQSSA-N 0.000 description 1
- JCALEFIXHVMTES-ZIADKAODSA-N methyl (3z)-3-[[4-[(dimethylamino)methyl]anilino]-[3-(3-ethoxy-3-oxopropyl)phenyl]methylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound CCOC(=O)CCC1=CC=CC(C(\NC=2C=CC(CN(C)C)=CC=2)=C\2C3=CC=C(C=C3NC/2=O)C(=O)OC)=C1 JCALEFIXHVMTES-ZIADKAODSA-N 0.000 description 1
- RPPPXRUSARQHLC-DQSJHHFOSA-N methyl (3z)-3-[[4-[(dipropylamino)methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(CN(CCC)CCC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O RPPPXRUSARQHLC-DQSJHHFOSA-N 0.000 description 1
- QXRQSNFYTPRXMN-DQSJHHFOSA-N methyl (3z)-3-[[4-[2-(4-hydroxypiperidin-1-yl)ethyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CCN1CCC(O)CC1 QXRQSNFYTPRXMN-DQSJHHFOSA-N 0.000 description 1
- YPCNHVIKYWKTMT-IZHYLOQSSA-N methyl (3z)-3-[[4-[2-(dimethylamino)-2-oxoethyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CC(=O)N(C)C)C=C1 YPCNHVIKYWKTMT-IZHYLOQSSA-N 0.000 description 1
- UGZDSGPCUPMYNG-MVJHLKBCSA-N methyl (3z)-3-[[4-[2-(dimethylamino)ethyl-(2-methoxybenzoyl)amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1N(CCN(C)C)C(=O)C1=CC=CC=C1OC UGZDSGPCUPMYNG-MVJHLKBCSA-N 0.000 description 1
- BQSKEHQIGVBVTC-ZIADKAODSA-N methyl (3z)-3-[[4-[2-(dimethylamino)ethyl-(furan-2-carbonyl)amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1N(CCN(C)C)C(=O)C1=CC=CO1 BQSKEHQIGVBVTC-ZIADKAODSA-N 0.000 description 1
- NSJWGYJIQYLIMC-QPLCGJKRSA-N methyl (3z)-3-[[4-[2-(dimethylamino)ethyl-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)CCN(C)C)C=C1 NSJWGYJIQYLIMC-QPLCGJKRSA-N 0.000 description 1
- YMLFEAONIWRRFP-FLWNBWAVSA-N methyl (3z)-3-[[4-[2-(dimethylamino)ethyl]anilino]-[3-(3-ethoxy-3-oxopropyl)phenyl]methylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound CCOC(=O)CCC1=CC=CC(C(\NC=2C=CC(CCN(C)C)=CC=2)=C\2C3=CC=C(C=C3NC/2=O)C(=O)OC)=C1 YMLFEAONIWRRFP-FLWNBWAVSA-N 0.000 description 1
- NVBPVILMPXSVFV-ZIADKAODSA-N methyl (3z)-3-[[4-[2-(dimethylamino)ethylsulfonyl-[2-(dimethylamino)-2-oxoethyl]amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(CC(=O)N(C)C)S(=O)(=O)CCN(C)C)C=C1 NVBPVILMPXSVFV-ZIADKAODSA-N 0.000 description 1
- FGWGAUNAIRDVBK-IZHYLOQSSA-N methyl (3z)-3-[[4-[2-(ethylamino)ethyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(CCNCC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O FGWGAUNAIRDVBK-IZHYLOQSSA-N 0.000 description 1
- KNRKOFDOYIKJGR-RQZHXJHFSA-N methyl (3z)-3-[[4-[3-(dimethylamino)propyl-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)CCCN(C)C)C=C1 KNRKOFDOYIKJGR-RQZHXJHFSA-N 0.000 description 1
- BOISFNGZPBTCBT-RQZHXJHFSA-N methyl (3z)-3-[[4-[3-(dimethylamino)propylcarbamoyl-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)NCCCN(C)C)C=C1 BOISFNGZPBTCBT-RQZHXJHFSA-N 0.000 description 1
- PFQBJQWYSLDVPT-KARKAFJISA-N methyl (3z)-3-[[4-[3-[benzyl(methyl)amino]propanoyl-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1N(C)C(=O)CCN(C)CC1=CC=CC=C1 PFQBJQWYSLDVPT-KARKAFJISA-N 0.000 description 1
- UTKGHSVTHCHCCU-IZHYLOQSSA-N methyl (3z)-3-[[4-[[(2-amino-2-oxoethyl)-methylamino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(C)CC(N)=O)C=C1 UTKGHSVTHCHCCU-IZHYLOQSSA-N 0.000 description 1
- IGGCSJYXULTKMB-RQZHXJHFSA-N methyl (3z)-3-[[4-[[1,3-dioxolan-2-ylmethyl(methyl)amino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CN(C)CC1OCCO1 IGGCSJYXULTKMB-RQZHXJHFSA-N 0.000 description 1
- RKNFAHWSKNXPAS-DQSJHHFOSA-N methyl (3z)-3-[[4-[[2-(2-methoxyethoxy)ethyl-methylamino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(CN(C)CCOCCOC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O RKNFAHWSKNXPAS-DQSJHHFOSA-N 0.000 description 1
- SOQPLBVBEMDMBB-KNWKATPGSA-N methyl (3z)-3-[[4-[[2-(4-benzylpiperazin-1-yl)acetyl]-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1N(C)C(=O)CN(CC1)CCN1CC1=CC=CC=C1 SOQPLBVBEMDMBB-KNWKATPGSA-N 0.000 description 1
- LGPFPZWGWQZVGL-FLWNBWAVSA-N methyl (3z)-3-[[4-[[2-(dimethylamino)-2-oxoethyl]-[3-(dimethylamino)propylsulfonyl]amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(CC(=O)N(C)C)S(=O)(=O)CCCN(C)C)C=C1 LGPFPZWGWQZVGL-FLWNBWAVSA-N 0.000 description 1
- VBLVPTZXOOSQHZ-QPLCGJKRSA-N methyl (3z)-3-[[4-[[2-(dimethylamino)acetyl]-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CN(C)C)C=C1 VBLVPTZXOOSQHZ-QPLCGJKRSA-N 0.000 description 1
- CLMURYIACIHACU-RQZHXJHFSA-N methyl (3z)-3-[[4-[[2-(dimethylamino)ethyl-methylamino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(C)CCN(C)C)C=C1 CLMURYIACIHACU-RQZHXJHFSA-N 0.000 description 1
- OEYMBRUKBJIOJL-QPLCGJKRSA-N methyl (3z)-3-[[4-[[2-(ethylamino)acetyl]-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(C)C(=O)CNCC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O OEYMBRUKBJIOJL-QPLCGJKRSA-N 0.000 description 1
- LLRYASAHXGEORL-ZIADKAODSA-N methyl (3z)-3-[[4-[[2-[2-(dimethylamino)ethyl-methylamino]acetyl]-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CN(C)CCN(C)C)C=C1 LLRYASAHXGEORL-ZIADKAODSA-N 0.000 description 1
- KULVOIVLYMLJJG-MVJHLKBCSA-N methyl (3z)-3-[[4-[[2-[benzyl(methyl)amino]acetyl]-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1N(C)C(=O)CN(C)CC1=CC=CC=C1 KULVOIVLYMLJJG-MVJHLKBCSA-N 0.000 description 1
- GCSYCCHPGMVUKA-ZIADKAODSA-N methyl (3z)-3-[[4-[[2-[ethyl(propyl)amino]acetyl]-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(C)C(=O)CN(CC)CCC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O GCSYCCHPGMVUKA-ZIADKAODSA-N 0.000 description 1
- PRZMRJVQKPDLFE-DQSJHHFOSA-N methyl (3z)-3-[[4-[[2-amino-4-methoxy-2-(2-methoxyethyl)butanoyl]-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(C)C(=O)C(N)(CCOC)CCOC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O PRZMRJVQKPDLFE-DQSJHHFOSA-N 0.000 description 1
- RIJRLDYGGPGPOI-IZHYLOQSSA-N methyl (3z)-3-[[4-[[2-aminoethyl(methyl)amino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(C)CCN)C=C1 RIJRLDYGGPGPOI-IZHYLOQSSA-N 0.000 description 1
- QFDIOUCLNGGUQP-QPLCGJKRSA-N methyl (3z)-3-[[4-[[2-methoxyethyl(methyl)amino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(CN(C)CCOC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O QFDIOUCLNGGUQP-QPLCGJKRSA-N 0.000 description 1
- UNCDJZOZMSPZIC-DQSJHHFOSA-N methyl (3z)-3-[[4-[[3-(dimethylamino)propyl-methylamino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(C)CCCN(C)C)C=C1 UNCDJZOZMSPZIC-DQSJHHFOSA-N 0.000 description 1
- XHJOGQMWAYMEDJ-KTMFPKCZSA-N methyl (3z)-3-[[4-[[benzyl(ethyl)amino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C=1C=C(N\C(=C/2C3=CC=C(C=C3NC\2=O)C(=O)OC)C=2C=CC=CC=2)C=CC=1CN(CC)CC1=CC=CC=C1 XHJOGQMWAYMEDJ-KTMFPKCZSA-N 0.000 description 1
- OFOIGKQPRKLLKH-QPLCGJKRSA-N methyl (3z)-3-[[4-[[bis(2-hydroxyethyl)amino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(CCO)CCO)C=C1 OFOIGKQPRKLLKH-QPLCGJKRSA-N 0.000 description 1
- FQHSDNRZQHBVIC-DQSJHHFOSA-N methyl (3z)-3-[[4-[[di(propan-2-yl)amino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(C(C)C)C(C)C)C=C1 FQHSDNRZQHBVIC-DQSJHHFOSA-N 0.000 description 1
- RVDUOGHPXADGKD-IZHYLOQSSA-N methyl (3z)-3-[[4-[[ethyl(methyl)amino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(CN(C)CC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O RVDUOGHPXADGKD-IZHYLOQSSA-N 0.000 description 1
- AOUHPEGJMFYYFU-RQZHXJHFSA-N methyl (3z)-3-[[4-[[ethyl(propyl)amino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(CN(CC)CCC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O AOUHPEGJMFYYFU-RQZHXJHFSA-N 0.000 description 1
- OULCGLUBKXTBRA-KTMFPKCZSA-N methyl (3z)-3-[[4-[[methyl(2-phenylethyl)amino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CN(C)CCC1=CC=CC=C1 OULCGLUBKXTBRA-KTMFPKCZSA-N 0.000 description 1
- LGYZWMSAASYNAN-IZHYLOQSSA-N methyl (3z)-3-[[4-[acetyl(2-aminoethyl)amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(CCN)C(C)=O)C=C1 LGYZWMSAASYNAN-IZHYLOQSSA-N 0.000 description 1
- ICWCEAPXTJICQR-FLWNBWAVSA-N methyl (3z)-3-[[4-[acetyl-(2-oxo-2-piperidin-1-ylethyl)amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1N(C(C)=O)CC(=O)N1CCCCC1 ICWCEAPXTJICQR-FLWNBWAVSA-N 0.000 description 1
- PKXSPUDURLLHHG-RQZHXJHFSA-N methyl (3z)-3-[[4-[acetyl-[2-(dimethylamino)-2-oxoethyl]amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(CC(=O)N(C)C)C(C)=O)C=C1 PKXSPUDURLLHHG-RQZHXJHFSA-N 0.000 description 1
- ZVFWAJHCDZHFCR-RQZHXJHFSA-N methyl (3z)-3-[[4-[acetyl-[2-(dimethylamino)ethyl]amino]-3-aminoanilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(CCN(C)C)C(C)=O)C(N)=C1 ZVFWAJHCDZHFCR-RQZHXJHFSA-N 0.000 description 1
- PTQKFPKUOYEZHW-QPLCGJKRSA-N methyl (3z)-3-[[4-[acetyl-[2-(methylamino)ethyl]amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(C(C)=O)CCNC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O PTQKFPKUOYEZHW-QPLCGJKRSA-N 0.000 description 1
- SYTKWJSZNMXBJR-RQZHXJHFSA-N methyl (3z)-3-[[4-[acetyl-[3-(methylamino)propyl]amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(C(C)=O)CCCNC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O SYTKWJSZNMXBJR-RQZHXJHFSA-N 0.000 description 1
- INOGNMCSLFRZAV-KTMFPKCZSA-N methyl (3z)-3-[[4-[benzoyl-[2-(dimethylamino)ethyl]amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1N(CCN(C)C)C(=O)C1=CC=CC=C1 INOGNMCSLFRZAV-KTMFPKCZSA-N 0.000 description 1
- OFWIFELCQOEIDW-MVJHLKBCSA-N methyl (3z)-3-[[4-[benzyl-[2-(dimethylamino)acetyl]amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1N(C(=O)CN(C)C)CC1=CC=CC=C1 OFWIFELCQOEIDW-MVJHLKBCSA-N 0.000 description 1
- RZRQHIPUCVMBGN-DTTHWBISSA-N methyl (3z)-3-[[4-[benzyl-[2-[benzyl(methyl)amino]acetyl]amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1N(C(=O)CN(C)CC=1C=CC=CC=1)CC1=CC=CC=C1 RZRQHIPUCVMBGN-DTTHWBISSA-N 0.000 description 1
- RWLCROIPWSUHJF-ZIADKAODSA-N methyl (3z)-3-[[4-[butyl-[2-(dimethylamino)acetyl]amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(C(=O)CN(C)C)CCCC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O RWLCROIPWSUHJF-ZIADKAODSA-N 0.000 description 1
- NFDQVNGHDIJKMW-VHXPQNKSSA-N methyl (3z)-3-[[4-[cyanomethyl(methylsulfonyl)amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(CC#N)S(C)(=O)=O)C=C1 NFDQVNGHDIJKMW-VHXPQNKSSA-N 0.000 description 1
- VNXMCZXSIRMZPI-VHXPQNKSSA-N methyl (3z)-3-[[4-[dimethylcarbamoyl(methyl)amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)N(C)C)C=C1 VNXMCZXSIRMZPI-VHXPQNKSSA-N 0.000 description 1
- WRRCRNUGELDDKU-FLWNBWAVSA-N methyl (3z)-3-[[4-[methyl-[2-(4-methyl-1,4-diazepan-1-yl)acetyl]amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1N(C)C(=O)CN1CCCN(C)CC1 WRRCRNUGELDDKU-FLWNBWAVSA-N 0.000 description 1
- YSAYJJLSESTVIV-QNGOZBTKSA-N methyl (3z)-3-[[4-[methyl-[2-(4-methylpiperazin-1-yl)acetyl]amino]anilino]methylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C\NC(C=C1)=CC=C1N(C)C(=O)CN1CCN(C)CC1 YSAYJJLSESTVIV-QNGOZBTKSA-N 0.000 description 1
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- PNKZFTFFNCJZSO-UHFFFAOYSA-N methyl 1-acetyl-3-[hydroxy-[4-(3-methoxy-3-oxopropyl)phenyl]methylidene]-2-oxoindole-6-carboxylate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C(O)=C1C2=CC=C(C(=O)OC)C=C2N(C(C)=O)C1=O PNKZFTFFNCJZSO-UHFFFAOYSA-N 0.000 description 1
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- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2
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- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/155—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/215—Radicals derived from nitrogen analogues of carbonic acid
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
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EP04030770 | 2004-12-24 | ||
EP04030770.4 | 2004-12-24 | ||
PCT/EP2005/057002 WO2006067165A2 (en) | 2004-12-24 | 2005-12-21 | Indolidone derivatives for the treatment or prevention of fibrotic diseases |
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AU2005318126A1 AU2005318126A1 (en) | 2006-06-29 |
AU2005318126B2 true AU2005318126B2 (en) | 2011-11-24 |
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AU2005318126A Active AU2005318126B2 (en) | 2004-12-24 | 2005-12-21 | Indolidone derivatives for the treatment or prevention of fibrotic diseases |
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2005
- 2005-12-16 PE PE2005001476A patent/PE20060777A1/es not_active Application Discontinuation
- 2005-12-20 US US11/275,223 patent/US20060142373A1/en not_active Abandoned
- 2005-12-21 RS RS20130037A patent/RS52653B/en unknown
- 2005-12-21 EP EP10184949.5A patent/EP2384751B1/en active Active
- 2005-12-21 ES ES14190398T patent/ES2797546T3/es active Active
- 2005-12-21 EA EA200701175A patent/EA015011B1/ru not_active IP Right Cessation
- 2005-12-21 HU HUE14190398A patent/HUE050998T2/hu unknown
- 2005-12-21 ES ES05823930T patent/ES2399270T3/es active Active
- 2005-12-21 EP EP14190398.9A patent/EP2878297B1/en active Active
- 2005-12-21 WO PCT/EP2005/057002 patent/WO2006067165A2/en active Application Filing
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