US20060142373A1 - Medicaments for the Treatment or Prevention of Fibrotic Diseases - Google Patents
Medicaments for the Treatment or Prevention of Fibrotic Diseases Download PDFInfo
- Publication number
- US20060142373A1 US20060142373A1 US11/275,223 US27522305A US2006142373A1 US 20060142373 A1 US20060142373 A1 US 20060142373A1 US 27522305 A US27522305 A US 27522305A US 2006142373 A1 US2006142373 A1 US 2006142373A1
- Authority
- US
- United States
- Prior art keywords
- phenyl
- methylene
- indolinone
- group
- anilino
- 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.)
- Abandoned
Links
- 230000003176 fibrotic effect Effects 0.000 title claims abstract description 22
- 201000010099 disease Diseases 0.000 title claims abstract description 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 16
- 239000003814 drug Substances 0.000 title claims abstract description 8
- 230000002265 prevention Effects 0.000 title abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 38
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical class C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 claims abstract description 9
- -1 C1-3-alkoxy-carbonyl Chemical group 0.000 claims description 224
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 188
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 153
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 89
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 84
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 53
- 125000006842 cycloalkyleneimino group Chemical group 0.000 claims description 53
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 52
- 125000000217 alkyl group Chemical group 0.000 claims description 51
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 49
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 44
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 42
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 35
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 35
- 229910052760 oxygen Inorganic materials 0.000 claims description 35
- 239000001301 oxygen Substances 0.000 claims description 35
- 125000001072 heteroaryl group Chemical group 0.000 claims description 34
- 125000006563 (C1-3) alkylaminocarbonyl group Chemical group 0.000 claims description 33
- 239000013543 active substance Substances 0.000 claims description 33
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 33
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 32
- 229910052801 chlorine Inorganic materials 0.000 claims description 29
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 28
- 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims description 27
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 26
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 26
- 239000000460 chlorine Substances 0.000 claims description 26
- 125000006576 di-(C1-C3-alkyl)-aminocarbonyl group Chemical group 0.000 claims description 25
- 229910052731 fluorine Inorganic materials 0.000 claims description 25
- 239000011737 fluorine Substances 0.000 claims description 25
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
- 230000004761 fibrosis Effects 0.000 claims description 23
- 206010016654 Fibrosis Diseases 0.000 claims description 22
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 21
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 19
- 229910052794 bromium Inorganic materials 0.000 claims description 19
- 210000004072 lung Anatomy 0.000 claims description 19
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 19
- 208000005069 pulmonary fibrosis Diseases 0.000 claims description 19
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 18
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 18
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 18
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 17
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 17
- 229910052740 iodine Inorganic materials 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 14
- 239000005557 antagonist Substances 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 125000006602 (C1-C3) alkylsulfonylamino group Chemical group 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 125000001624 naphthyl group Chemical group 0.000 claims description 13
- 125000001153 fluoro group Chemical group F* 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims description 11
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 10
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 9
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- CRMYVRAWTZMAIV-ZIADKAODSA-N (3z)-3-[[4-[2-(diethylamino)ethylcarbamoyl]anilino]-phenylmethylidene]-6-ethyl-n-methyl-2-oxoindole-1-carboxamide Chemical compound C1=CC(C(=O)NCCN(CC)CC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(CC)C=C2N(C(=O)NC)C\1=O CRMYVRAWTZMAIV-ZIADKAODSA-N 0.000 claims description 8
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 8
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 238000007634 remodeling Methods 0.000 claims description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 208000019425 cirrhosis of liver Diseases 0.000 claims description 7
- NALBLJLOBICXRH-UHFFFAOYSA-N dinitrogen monohydride Chemical group N=[N] NALBLJLOBICXRH-UHFFFAOYSA-N 0.000 claims description 7
- 125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims description 7
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 7
- TUTAXIULGANIJO-RQZHXJHFSA-N 3-[4-[(z)-[4-[(dimethylamino)methyl]anilino]-(6-methoxycarbonyl-2-oxo-1h-indol-3-ylidene)methyl]phenyl]propanoic acid Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC(CCC(O)=O)=CC=1)\NC1=CC=C(CN(C)C)C=C1 TUTAXIULGANIJO-RQZHXJHFSA-N 0.000 claims description 6
- ZUWLEBRSSYJVEQ-VHXPQNKSSA-N methyl (3z)-3-[[4-[(2-aminoacetyl)-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=C1 ZUWLEBRSSYJVEQ-VHXPQNKSSA-N 0.000 claims description 6
- CPMDPSXJELVGJG-UHFFFAOYSA-N methyl 2-hydroxy-3-[N-[4-[methyl-[2-(4-methylpiperazin-1-yl)acetyl]amino]phenyl]-C-phenylcarbonimidoyl]-1H-indole-6-carboxylate Chemical compound OC=1NC2=CC(=CC=C2C=1C(=NC1=CC=C(C=C1)N(C(CN1CCN(CC1)C)=O)C)C1=CC=CC=C1)C(=O)OC CPMDPSXJELVGJG-UHFFFAOYSA-N 0.000 claims description 6
- 125000002950 monocyclic group Chemical group 0.000 claims description 6
- 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
- WCWCVRCRBPFOOB-JWGURIENSA-N (3z)-n-ethyl-3-[[4-[methyl-[2-(4-methylpiperazin-1-yl)acetyl]amino]anilino]methylidene]-2-oxo-1h-indole-6-carboxamide Chemical compound O=C1NC2=CC(C(=O)NCC)=CC=C2\C1=C\NC(C=C1)=CC=C1N(C)C(=O)CN1CCN(C)CC1 WCWCVRCRBPFOOB-JWGURIENSA-N 0.000 claims description 5
- DUIOKOWKQZMOFY-RQZHXJHFSA-N 3-[3-[(z)-(6-methoxycarbonyl-2-oxo-1h-indol-3-ylidene)-[4-(1-methylimidazol-2-yl)anilino]methyl]phenyl]propanoic acid Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=C(CCC(O)=O)C=CC=1)\NC(C=C1)=CC=C1C1=NC=CN1C DUIOKOWKQZMOFY-RQZHXJHFSA-N 0.000 claims description 5
- UFTFYMDMERXPRI-DQSJHHFOSA-N 3-[3-[(z)-[4-[2-(dimethylamino)ethyl]anilino]-(6-methoxycarbonyl-2-oxo-1h-indol-3-ylidene)methyl]phenyl]propanoic acid Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=C(CCC(O)=O)C=CC=1)\NC1=CC=C(CCN(C)C)C=C1 UFTFYMDMERXPRI-DQSJHHFOSA-N 0.000 claims description 5
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 5
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- ZACMGSKEGVXBMJ-MRCUWXFGSA-N methyl (3z)-3-[(cyclohexylamino)-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1CCCCC1 ZACMGSKEGVXBMJ-MRCUWXFGSA-N 0.000 claims description 5
- 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 claims description 5
- IZTCGPDAIPBHGU-BOPFTXTBSA-N methyl (3z)-3-[[4-[(dimethylamino)methyl]anilino]methylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C\NC1=CC=C(CN(C)C)C=C1 IZTCGPDAIPBHGU-BOPFTXTBSA-N 0.000 claims description 5
- 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 claims description 5
- WDLKBZLGTNDINZ-PDGQHHTCSA-N methyl (3z)-3-[[4-[[2-(dimethylamino)acetyl]-methylamino]anilino]methylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C\NC1=CC=C(N(C)C(=O)CN(C)C)C=C1 WDLKBZLGTNDINZ-PDGQHHTCSA-N 0.000 claims description 5
- 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 claims description 5
- UEIQMVYRNFWKTR-FCQUAONHSA-N methyl (3z)-3-[[4-[methyl(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(C)S(C)(=O)=O)C=C1 UEIQMVYRNFWKTR-FCQUAONHSA-N 0.000 claims description 5
- YUGAQWBIOKQVPV-UHFFFAOYSA-N methyl 3-[N-[4-[acetyl-[3-(dimethylamino)propyl]amino]phenyl]-C-phenylcarbonimidoyl]-2-hydroxy-1H-indole-6-carboxylate Chemical compound CC(=O)N(CCCN(C)C)C1=CC=C(C=C1)N=C(C2=CC=CC=C2)C3=C(NC4=C3C=CC(=C4)C(=O)OC)O YUGAQWBIOKQVPV-UHFFFAOYSA-N 0.000 claims description 5
- 229940002612 prodrug Drugs 0.000 claims description 5
- 239000000651 prodrug Chemical group 0.000 claims description 5
- 201000002793 renal fibrosis Diseases 0.000 claims description 5
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 5
- OGAUJAMHPFSPAH-FCQUAONHSA-N (3z)-3-[(4-carbamoylanilino)-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(C(N)=O)C=C1 OGAUJAMHPFSPAH-FCQUAONHSA-N 0.000 claims description 4
- XZILZMAYXCICSV-VXPUYCOJSA-N (3z)-3-[(cyclohexylamino)-phenylmethylidene]-2-oxo-1h-indole-6-carboxylic acid Chemical compound O=C1NC2=CC(C(=O)O)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1CCCCC1 XZILZMAYXCICSV-VXPUYCOJSA-N 0.000 claims description 4
- CZGPSLZNGWWGCV-FCQUAONHSA-N (3z)-3-[(cyclohexylamino)-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)\NC1CCCCC1 CZGPSLZNGWWGCV-FCQUAONHSA-N 0.000 claims description 4
- GLQNMTKCBJMCEK-DQSJHHFOSA-N (3z)-3-[[3-(diethylaminomethyl)anilino]-phenylmethylidene]-6-ethyl-n-methyl-2-oxoindole-1-carboxamide Chemical compound CCN(CC)CC1=CC=CC(N\C(=C/2C3=CC=C(CC)C=C3N(C(=O)NC)C\2=O)C=2C=CC=CC=2)=C1 GLQNMTKCBJMCEK-DQSJHHFOSA-N 0.000 claims description 4
- 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 claims description 4
- 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 claims description 4
- NNEPNKIGXXNLOL-IZHYLOQSSA-N (3z)-3-[[4-(morpholin-4-ylmethyl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylic acid Chemical compound O=C1NC2=CC(C(=O)O)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CN1CCOCC1 NNEPNKIGXXNLOL-IZHYLOQSSA-N 0.000 claims description 4
- PZRKHKYKJFNDAL-MBYMXDHUSA-N (3z)-3-[[4-[(3s,5r)-3,5-dimethylpiperazine-1-carbonyl]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)\NC(C=C1)=CC=C1C(=O)N1C[C@H](C)N[C@H](C)C1 PZRKHKYKJFNDAL-MBYMXDHUSA-N 0.000 claims description 4
- YMWIIZYJFMWFTC-GSXVUDQXSA-N (3z)-3-[[4-[(3s,5r)-3,5-dimethylpiperazine-1-carbonyl]anilino]-phenylmethylidene]-n-ethyl-2-oxo-1h-indole-6-carboxamide Chemical compound O=C1NC2=CC(C(=O)NCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1C(=O)N1C[C@H](C)N[C@H](C)C1 YMWIIZYJFMWFTC-GSXVUDQXSA-N 0.000 claims description 4
- WGNFPWQYQPILCJ-QPLCGJKRSA-N (3z)-3-[[4-[(4-methylpiperazin-1-yl)methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylic acid Chemical compound C1CN(C)CCN1CC(C=C1)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(O)=O)C=C2NC\1=O WGNFPWQYQPILCJ-QPLCGJKRSA-N 0.000 claims description 4
- WCLVQWHXIIKMSQ-QPLCGJKRSA-N (3z)-3-[[4-[(dimethylamino)methyl]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(CN(C)C)C=C1 WCLVQWHXIIKMSQ-QPLCGJKRSA-N 0.000 claims description 4
- UIYHJVSSHGDKDN-PDGQHHTCSA-N (3z)-3-[[4-[(dimethylamino)methyl]anilino]methylidene]-n-ethyl-2-oxo-1h-indole-6-carboxamide Chemical compound O=C1NC2=CC(C(=O)NCC)=CC=C2\C1=C\NC1=CC=C(CN(C)C)C=C1 UIYHJVSSHGDKDN-PDGQHHTCSA-N 0.000 claims description 4
- UTJIJEQJEGRNSJ-ZIADKAODSA-N (3z)-3-[[4-[2-(diethylamino)ethoxy]anilino]-phenylmethylidene]-6-ethyl-n-methyl-2-oxoindole-1-carboxamide Chemical compound C1=CC(OCCN(CC)CC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(CC)C=C2N(C(=O)NC)C\1=O UTJIJEQJEGRNSJ-ZIADKAODSA-N 0.000 claims description 4
- VHNIIPBFZCVDRK-VHXPQNKSSA-N (3z)-3-[[4-[2-(dimethylamino)ethoxy]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylic acid Chemical compound C1=CC(OCCN(C)C)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(O)=O)C=C2NC\1=O VHNIIPBFZCVDRK-VHXPQNKSSA-N 0.000 claims description 4
- 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 claims description 4
- BGXJBXKNGLFWTE-QPLCGJKRSA-N (3z)-3-[[4-[2-(dimethylamino)ethoxy]anilino]-phenylmethylidene]-n-ethyl-2-oxo-1h-indole-6-carboxamide Chemical compound O=C1NC2=CC(C(=O)NCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(OCCN(C)C)C=C1 BGXJBXKNGLFWTE-QPLCGJKRSA-N 0.000 claims description 4
- AGFKSCPLDAVZSW-ZIADKAODSA-N (3z)-3-[[4-[2-(dimethylamino)ethyl-ethylcarbamoyl]anilino]-phenylmethylidene]-6-ethyl-n-methyl-2-oxoindole-1-carboxamide Chemical compound C1=CC(C(=O)N(CCN(C)C)CC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(CC)C=C2N(C(=O)NC)C\1=O AGFKSCPLDAVZSW-ZIADKAODSA-N 0.000 claims description 4
- DTGOGIFSACOYRD-DQSJHHFOSA-N (3z)-3-[[4-[2-(dimethylamino)ethyl-methylsulfonylamino]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(N(CCN(C)C)S(C)(=O)=O)C=C1 DTGOGIFSACOYRD-DQSJHHFOSA-N 0.000 claims description 4
- IMPLASSOUGGFTO-RQZHXJHFSA-N (3z)-3-[[4-[2-(dimethylamino)ethyl-methylsulfonylamino]anilino]-phenylmethylidene]-n-ethyl-2-oxo-1h-indole-6-carboxamide Chemical compound O=C1NC2=CC(C(=O)NCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(CCN(C)C)S(C)(=O)=O)C=C1 IMPLASSOUGGFTO-RQZHXJHFSA-N 0.000 claims description 4
- IXLWEGLCDIDAPI-RQZHXJHFSA-N (3z)-3-[[4-[2-(dimethylamino)ethyl]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(CCN(C)C)C=C1 IXLWEGLCDIDAPI-RQZHXJHFSA-N 0.000 claims description 4
- CLDAEJHVEBCEMQ-DQSJHHFOSA-N (3z)-3-[[4-[3-(dimethylamino)propyl-methylsulfonylamino]anilino]-phenylmethylidene]-n-ethyl-2-oxo-1h-indole-6-carboxamide Chemical compound O=C1NC2=CC(C(=O)NCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(CCCN(C)C)S(C)(=O)=O)C=C1 CLDAEJHVEBCEMQ-DQSJHHFOSA-N 0.000 claims description 4
- IQKBTFDFJXIXTI-KTMFPKCZSA-N (3z)-3-[[4-[3-(dimethylamino)propyl-propanoylamino]anilino]-phenylmethylidene]-6-ethyl-n-methyl-2-oxoindole-1-carboxamide Chemical compound C1=CC(N(CCCN(C)C)C(=O)CC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(CC)C=C2N(C(=O)NC)C\1=O IQKBTFDFJXIXTI-KTMFPKCZSA-N 0.000 claims description 4
- DOUKXCLPSNHVBS-DQSJHHFOSA-N (3z)-3-[[4-[[2-(dimethylamino)-2-oxoethyl]-methylsulfonylamino]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(N(CC(=O)N(C)C)S(C)(=O)=O)C=C1 DOUKXCLPSNHVBS-DQSJHHFOSA-N 0.000 claims description 4
- CHCGJWCRDGTQMX-DQSJHHFOSA-N (3z)-3-[[4-[[2-(dimethylamino)acetyl]-methylamino]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(N(C)C(=O)CN(C)C)C=C1 CHCGJWCRDGTQMX-DQSJHHFOSA-N 0.000 claims description 4
- JVOASSRFSRQUDN-RQZHXJHFSA-N (3z)-3-[[4-[[2-(dimethylamino)acetyl]-methylamino]anilino]-phenylmethylidene]-n-ethyl-2-oxo-1h-indole-6-carboxamide Chemical compound O=C1NC2=CC(C(=O)NCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CN(C)C)C=C1 JVOASSRFSRQUDN-RQZHXJHFSA-N 0.000 claims description 4
- OHUYWTKAWLTSCW-DQSJHHFOSA-N (3z)-3-[[4-[[2-[2-(dimethylamino)ethyl-methylamino]acetyl]-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylic acid Chemical compound C1=CC(N(C)C(=O)CN(C)CCN(C)C)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(O)=O)C=C2NC\1=O OHUYWTKAWLTSCW-DQSJHHFOSA-N 0.000 claims description 4
- ZQOZIMCYMYZQQK-ZIADKAODSA-N (3z)-3-[[4-[acetyl-[2-(dimethylamino)ethyl]amino]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(N(CCN(C)C)C(C)=O)C=C1 ZQOZIMCYMYZQQK-ZIADKAODSA-N 0.000 claims description 4
- ZYSFQPYDGIWDSA-DQSJHHFOSA-N (3z)-3-[[4-[acetyl-[2-(dimethylamino)ethyl]amino]anilino]-phenylmethylidene]-n-ethyl-2-oxo-1h-indole-6-carboxamide Chemical compound O=C1NC2=CC(C(=O)NCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(CCN(C)C)C(C)=O)C=C1 ZYSFQPYDGIWDSA-DQSJHHFOSA-N 0.000 claims description 4
- YTHNOKLCSDZEQF-FLWNBWAVSA-N (3z)-3-[[4-[acetyl-[3-(dimethylamino)propyl]amino]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(N(CCCN(C)C)C(C)=O)C=C1 YTHNOKLCSDZEQF-FLWNBWAVSA-N 0.000 claims description 4
- SZETXTFRBXNRRT-ZIADKAODSA-N (3z)-3-[[4-[acetyl-[3-(dimethylamino)propyl]amino]anilino]-phenylmethylidene]-n-ethyl-2-oxo-1h-indole-6-carboxamide Chemical compound O=C1NC2=CC(C(=O)NCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(CCCN(C)C)C(C)=O)C=C1 SZETXTFRBXNRRT-ZIADKAODSA-N 0.000 claims description 4
- KEHNCEDHZGQSNP-DQSJHHFOSA-N (3z)-3-[[4-[methyl-[2-(4-methylpiperazin-1-yl)acetyl]amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylic acid Chemical compound C=1C=C(N\C(=C/2C3=CC=C(C=C3NC\2=O)C(O)=O)C=2C=CC=CC=2)C=CC=1N(C)C(=O)CN1CCN(C)CC1 KEHNCEDHZGQSNP-DQSJHHFOSA-N 0.000 claims description 4
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- UWSIFWPDYFEXCS-DQSJHHFOSA-N (3z)-6-ethyl-n-methyl-3-[[4-(4-methylpiperazine-1-carbonyl)anilino]-phenylmethylidene]-2-oxoindole-1-carboxamide Chemical compound O=C1N(C(=O)NC)C2=CC(CC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1C(=O)N1CCN(C)CC1 UWSIFWPDYFEXCS-DQSJHHFOSA-N 0.000 claims description 4
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- ADGROYOHFKXNNA-KTMFPKCZSA-N (3z)-6-ethyl-n-methyl-3-[[4-[methyl-[2-(4-methylpiperazin-1-yl)acetyl]amino]anilino]-phenylmethylidene]-2-oxoindole-1-carboxamide Chemical compound O=C1N(C(=O)NC)C2=CC(CC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1N(C)C(=O)CN1CCN(C)CC1 ADGROYOHFKXNNA-KTMFPKCZSA-N 0.000 claims description 4
- KSUCWRVJHANYQF-MVJHLKBCSA-N (3z)-n,n-diethyl-3-[[4-[methyl-[2-(4-methylpiperazin-1-yl)acetyl]amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxamide Chemical compound O=C1NC2=CC(C(=O)N(CC)CC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1N(C)C(=O)CN1CCN(C)CC1 KSUCWRVJHANYQF-MVJHLKBCSA-N 0.000 claims description 4
- AXYULAMMHLESBS-DQSJHHFOSA-N (3z)-n-ethyl-3-[[4-(4-ethylpiperazine-1-carbonyl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxamide Chemical compound O=C1NC2=CC(C(=O)NCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1C(=O)N1CCN(CC)CC1 AXYULAMMHLESBS-DQSJHHFOSA-N 0.000 claims description 4
- IUYCDHJEQQHSGL-RQZHXJHFSA-N (3z)-n-ethyl-3-[[4-(4-methylpiperazine-1-carbonyl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxamide Chemical compound O=C1NC2=CC(C(=O)NCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1C(=O)N1CCN(C)CC1 IUYCDHJEQQHSGL-RQZHXJHFSA-N 0.000 claims description 4
- YXUCEYHUMMDUOT-FLWNBWAVSA-N (3z)-n-ethyl-3-[[4-[methyl-[2-(4-methylpiperazin-1-yl)acetyl]amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxamide Chemical compound O=C1NC2=CC(C(=O)NCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1N(C)C(=O)CN1CCN(C)CC1 YXUCEYHUMMDUOT-FLWNBWAVSA-N 0.000 claims description 4
- 125000006597 (C1-C3) alkylcarbonylamino group Chemical group 0.000 claims description 4
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 4
- KJTHGONTJGVGKM-RQZHXJHFSA-N 3-[3-[(z)-[4-[(dimethylamino)methyl]anilino]-(6-methoxycarbonyl-2-oxo-1h-indol-3-ylidene)methyl]phenyl]propanoic acid Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=C(CCC(O)=O)C=CC=1)\NC1=CC=C(CN(C)C)C=C1 KJTHGONTJGVGKM-RQZHXJHFSA-N 0.000 claims description 4
- JGAJAFXLHHPVTP-FCQUAONHSA-N 4-[[(z)-[6-ethyl-1-(methylcarbamoyl)-2-oxoindol-3-ylidene]-phenylmethyl]amino]benzoic acid Chemical compound O=C1N(C(=O)NC)C2=CC(CC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(C(O)=O)C=C1 JGAJAFXLHHPVTP-FCQUAONHSA-N 0.000 claims description 4
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 4
- YLJGNMFEAJARMT-IZHYLOQSSA-N BI-4659 Chemical compound O=C1NC2=CC(C(=O)NCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(C)C)C=C1 YLJGNMFEAJARMT-IZHYLOQSSA-N 0.000 claims description 4
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 claims description 4
- BHQGFGYDTDANFA-PSMUHQEKSA-N O=C1N(C(=O)NC)C2=CC(CC)=CC=C2\C1=C(C=1C=CC=CC=1)\N[C@H]1CC[C@H](N(C)C)CC1 Chemical compound O=C1N(C(=O)NC)C2=CC(CC)=CC=C2\C1=C(C=1C=CC=CC=1)\N[C@H]1CC[C@H](N(C)C)CC1 BHQGFGYDTDANFA-PSMUHQEKSA-N 0.000 claims description 4
- 208000006673 asthma Diseases 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 239000000812 cholinergic antagonist Substances 0.000 claims description 4
- IXKSURGKVWEOIW-DQSJHHFOSA-N ethyl (3z)-3-[[4-[acetyl-[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)\NC1=CC=C(N(CCN(C)C)C(C)=O)C=C1 IXKSURGKVWEOIW-DQSJHHFOSA-N 0.000 claims description 4
- 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 claims description 4
- 125000002795 guanidino group Chemical group C(N)(=N)N* 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
- 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 claims description 4
- 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 claims description 4
- 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 claims description 4
- 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 claims description 4
- CIPWANLWCIHSJN-RQZHXJHFSA-N methyl (3z)-3-[[4-[[2-(dimethylamino)acetyl]-methylamino]-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(N(C)C(=O)CN(C)C)C(OC)=C1 CIPWANLWCIHSJN-RQZHXJHFSA-N 0.000 claims description 4
- 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 claims description 4
- CMSQYYMTWHIKRA-IZHYLOQSSA-N methyl (3z)-3-[[4-[[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)\NC1=CC=C(NC(=O)CN(C)C)C=C1 CMSQYYMTWHIKRA-IZHYLOQSSA-N 0.000 claims description 4
- QGKINQMQSPXIJG-QPLCGJKRSA-N methyl (3z)-3-[[4-[[2-amino-4-hydroxy-2-(2-hydroxyethyl)butanoyl]-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)C(N)(CCO)CCO)C=C1 QGKINQMQSPXIJG-QPLCGJKRSA-N 0.000 claims description 4
- BNCKHAYXFFVDTH-RQZHXJHFSA-N methyl (3z)-3-[[4-[methyl-(4-methylpiperazine-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)N1CCN(C)CC1 BNCKHAYXFFVDTH-RQZHXJHFSA-N 0.000 claims description 4
- KLUDIZHVAPHSKN-FLWNBWAVSA-N methyl (3z)-3-[[4-[methyl-[2-(1-methylpiperidin-4-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)CC1CCN(C)CC1 KLUDIZHVAPHSKN-FLWNBWAVSA-N 0.000 claims description 4
- 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 claims description 4
- ILLAFQLVCWQSQA-MRCUWXFGSA-N methyl (3z)-3-[anilino(phenyl)methylidene]-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=CC=C1 ILLAFQLVCWQSQA-MRCUWXFGSA-N 0.000 claims description 4
- NHWDWXPEPUAAAH-VHXPQNKSSA-N methyl 4-[[(z)-[6-ethyl-1-(methylcarbamoyl)-2-oxoindol-3-ylidene]-phenylmethyl]amino]benzoate Chemical compound O=C1N(C(=O)NC)C2=CC(CC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(C(=O)OC)C=C1 NHWDWXPEPUAAAH-VHXPQNKSSA-N 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
- JDWDCRAOGTXDKD-IZHYLOQSSA-N (3z)-3-[[4-[2-(dimethylamino)ethyl-methylsulfonylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylic acid Chemical compound C1=CC(N(CCN(C)C)S(C)(=O)=O)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(O)=O)C=C2NC\1=O JDWDCRAOGTXDKD-IZHYLOQSSA-N 0.000 claims description 3
- DTWRYSLEWSOAST-JWGURIENSA-N (3z)-3-[[4-[acetyl-[3-(dimethylamino)propyl]amino]anilino]methylidene]-n-ethyl-2-oxo-1h-indole-6-carboxamide Chemical compound O=C1NC2=CC(C(=O)NCC)=CC=C2\C1=C\NC1=CC=C(N(CCCN(C)C)C(C)=O)C=C1 DTWRYSLEWSOAST-JWGURIENSA-N 0.000 claims description 3
- XLEMLAQLFUOTLC-RQZHXJHFSA-N (3z)-3-[[4-[methyl-(2-morpholin-4-ylacetyl)amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylic acid Chemical compound C=1C=C(N\C(=C/2C3=CC=C(C=C3NC\2=O)C(O)=O)C=2C=CC=CC=2)C=CC=1N(C)C(=O)CN1CCOCC1 XLEMLAQLFUOTLC-RQZHXJHFSA-N 0.000 claims description 3
- RBCYCXVGIISHRT-ZIADKAODSA-N (3z)-6-ethyl-3-[[4-(4-ethylpiperazine-1-carbonyl)anilino]-phenylmethylidene]-n-methyl-2-oxoindole-1-carboxamide Chemical compound C1CN(CC)CCN1C(=O)C(C=C1)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(CC)C=C2N(C(=O)NC)C\1=O RBCYCXVGIISHRT-ZIADKAODSA-N 0.000 claims description 3
- JSTXJSLAAJAPDG-QPLCGJKRSA-N (3z)-6-ethyl-3-[[4-(ethylaminomethyl)anilino]-phenylmethylidene]-n-methyl-2-oxoindole-1-carboxamide Chemical compound C1=CC(CNCC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(CC)C=C2N(C(=O)NC)C\1=O JSTXJSLAAJAPDG-QPLCGJKRSA-N 0.000 claims description 3
- GNNMAPGYHFHFJB-QNGOZBTKSA-N (3z)-n-ethyl-2-oxo-3-[[4-(piperidin-1-ylmethyl)anilino]methylidene]-1h-indole-6-carboxamide Chemical compound O=C1NC2=CC(C(=O)NCC)=CC=C2\C1=C\NC(C=C1)=CC=C1CN1CCCCC1 GNNMAPGYHFHFJB-QNGOZBTKSA-N 0.000 claims description 3
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 3
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims description 3
- 125000006164 6-membered heteroaryl group Chemical group 0.000 claims description 3
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 3
- 208000019693 Lung disease Diseases 0.000 claims description 3
- 206010039710 Scleroderma Diseases 0.000 claims description 3
- 201000010001 Silicosis Diseases 0.000 claims description 3
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 3
- CREXVNNSNOKDHW-UHFFFAOYSA-N azaniumylideneazanide Chemical group N[N] CREXVNNSNOKDHW-UHFFFAOYSA-N 0.000 claims description 3
- 150000001721 carbon Chemical group 0.000 claims description 3
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 3
- 125000006844 cycloalkyleneimino-C1-3-alkyl group Chemical group 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- 229940121647 egfr inhibitor Drugs 0.000 claims description 3
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- HBJVBPWUOTUJLJ-ZIADKAODSA-N ethyl (3z)-3-[(4-benzylanilino)-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=CC=CC=C1 HBJVBPWUOTUJLJ-ZIADKAODSA-N 0.000 description 1
- MQFMJUAKVIHGAP-DQRAZIAOSA-N ethyl (3z)-3-[(4-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(Br)C=C1 MQFMJUAKVIHGAP-DQRAZIAOSA-N 0.000 description 1
- 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 1
- HULZHXOHFLVUNR-FCQUAONHSA-N ethyl (3z)-3-[(4-cyanoanilino)-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)C=C1 HULZHXOHFLVUNR-FCQUAONHSA-N 0.000 description 1
- PHZAEELHHMVCBJ-VHXPQNKSSA-N ethyl (3z)-3-[(4-ethoxyanilino)-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(OCC)C=C1 PHZAEELHHMVCBJ-VHXPQNKSSA-N 0.000 description 1
- RWRVSGMLPFNVGC-DQRAZIAOSA-N ethyl (3z)-3-[(4-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(F)C=C1 RWRVSGMLPFNVGC-DQRAZIAOSA-N 0.000 description 1
- ZVTHOGVLDFZJCE-DQRAZIAOSA-N ethyl (3z)-3-[(4-iodoanilino)-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(I)C=C1 ZVTHOGVLDFZJCE-DQRAZIAOSA-N 0.000 description 1
- 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 1
- IFFQFGXSWOSXKP-FCQUAONHSA-N ethyl (3z)-3-[(4-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(C)C=C1 IFFQFGXSWOSXKP-FCQUAONHSA-N 0.000 description 1
- SZNAKLOSBCUWEK-FCQUAONHSA-N ethyl (3z)-3-[(4-methylsulfanylanilino)-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(SC)C=C1 SZNAKLOSBCUWEK-FCQUAONHSA-N 0.000 description 1
- 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 1
- YWAAMCHASYQBPI-VHXPQNKSSA-N ethyl (3z)-3-[(n-(2-amino-2-oxoethyl)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)\N(CC(N)=O)C1=CC=CC=C1 YWAAMCHASYQBPI-VHXPQNKSSA-N 0.000 description 1
- SVTNYGVEBCIXBO-XDOYNYLZSA-N ethyl (3z)-3-[1-[4-[(dimethylamino)methyl]anilino]butylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C/1NC2=CC(C(=O)OCC)=CC=C2C\1=C(/CCC)NC1=CC=C(CN(C)C)C=C1 SVTNYGVEBCIXBO-XDOYNYLZSA-N 0.000 description 1
- LYKJSNSUSVJOCK-ZHZULCJRSA-N ethyl (3z)-3-[1-[4-[(dimethylamino)methyl]anilino]ethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(/C)NC1=CC=C(CN(C)C)C=C1 LYKJSNSUSVJOCK-ZHZULCJRSA-N 0.000 description 1
- ZFQCJYHRLVIXAN-VZCXRCSSSA-N ethyl (3z)-3-[1-[4-[(dimethylamino)methyl]anilino]propylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(/CC)NC1=CC=C(CN(C)C)C=C1 ZFQCJYHRLVIXAN-VZCXRCSSSA-N 0.000 description 1
- GEHMQROSGLELCO-GYHWCHFESA-N ethyl (3z)-3-[1-[4-[2-(dimethylamino)ethyl-methylsulfonylamino]anilino]butylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C/1NC2=CC(C(=O)OCC)=CC=C2C\1=C(/CCC)NC1=CC=C(N(CCN(C)C)S(C)(=O)=O)C=C1 GEHMQROSGLELCO-GYHWCHFESA-N 0.000 description 1
- UPQQSNJMYNDJRQ-FLFQWRMESA-N ethyl (3z)-3-[1-[4-[[2-(dimethylamino)acetyl]-methylamino]anilino]butylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C/1NC2=CC(C(=O)OCC)=CC=C2C\1=C(/CCC)NC1=CC=C(N(C)C(=O)CN(C)C)C=C1 UPQQSNJMYNDJRQ-FLFQWRMESA-N 0.000 description 1
- JRGQSUPXYLJIGB-JCMHNJIXSA-N ethyl (3z)-3-[1-[4-[[2-(dimethylamino)acetyl]-methylamino]anilino]ethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(/C)NC1=CC=C(N(C)C(=O)CN(C)C)C=C1 JRGQSUPXYLJIGB-JCMHNJIXSA-N 0.000 description 1
- HRDUWDJLEWNFMR-ATJXCDBQSA-N ethyl (3z)-3-[1-[4-[[2-(dimethylamino)acetyl]-methylamino]anilino]propylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(/CC)NC1=CC=C(N(C)C(=O)CN(C)C)C=C1 HRDUWDJLEWNFMR-ATJXCDBQSA-N 0.000 description 1
- FPCAYZUZSJHFLE-LCUIJRPUSA-N ethyl (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)OCC)=CC=C2C\1=C(/CCC)NC1=CC=C(N(CCCN(C)C)C(C)=O)C=C1 FPCAYZUZSJHFLE-LCUIJRPUSA-N 0.000 description 1
- QERMALCKFDOHQZ-ULJHMMPZSA-N ethyl (3z)-3-[1-[4-[acetyl-[3-(dimethylamino)propyl]amino]anilino]ethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(/C)NC1=CC=C(N(CCCN(C)C)C(C)=O)C=C1 QERMALCKFDOHQZ-ULJHMMPZSA-N 0.000 description 1
- HPRDNJKLSHVSFW-BZZOAKBMSA-N ethyl (3z)-3-[1-[4-[acetyl-[3-(dimethylamino)propyl]amino]anilino]propylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(/CC)NC1=CC=C(N(CCCN(C)C)C(C)=O)C=C1 HPRDNJKLSHVSFW-BZZOAKBMSA-N 0.000 description 1
- YGASJVGLHJEVQF-IZHYLOQSSA-N ethyl (3z)-3-[[3,5-dibromo-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(Br)=C(CN(C)C)C(Br)=C1 YGASJVGLHJEVQF-IZHYLOQSSA-N 0.000 description 1
- DXMBYNGILNYABD-QPLCGJKRSA-N ethyl (3z)-3-[[3,5-dibromo-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(Br)=C(N(C)C(=O)CN(C)C)C(Br)=C1 DXMBYNGILNYABD-QPLCGJKRSA-N 0.000 description 1
- KGLGZLLAQXVHMY-IZHYLOQSSA-N ethyl (3z)-3-[[3,5-dichloro-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(Cl)=C(CN(C)C)C(Cl)=C1 KGLGZLLAQXVHMY-IZHYLOQSSA-N 0.000 description 1
- BLNQSNMBZBYUDM-QPLCGJKRSA-N ethyl (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)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC(Cl)=C(N(C)C(=O)CN(C)C)C(Cl)=C1 BLNQSNMBZBYUDM-QPLCGJKRSA-N 0.000 description 1
- 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
- VIVWCLZPYSFYDJ-RQZHXJHFSA-N ethyl (3z)-3-[[3-acetamido-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(NC(C)=O)=C1 VIVWCLZPYSFYDJ-RQZHXJHFSA-N 0.000 description 1
- ANXZJZMZRUNILB-ZIADKAODSA-N ethyl (3z)-3-[[3-acetamido-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(NC(C)=O)=C1 ANXZJZMZRUNILB-ZIADKAODSA-N 0.000 description 1
- BINQPENHOYFNPB-IZHYLOQSSA-N ethyl (3z)-3-[[3-amino-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(N)=C1 BINQPENHOYFNPB-IZHYLOQSSA-N 0.000 description 1
- JTJOOQARWKSEOI-RQZHXJHFSA-N ethyl (3z)-3-[[3-amino-4-[2-(dimethylamino)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(C)C)S(C)(=O)=O)C(N)=C1 JTJOOQARWKSEOI-RQZHXJHFSA-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
- TZJRNTBXNYWUCH-IZHYLOQSSA-N ethyl (3z)-3-[[3-bromo-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(Br)=C1 TZJRNTBXNYWUCH-IZHYLOQSSA-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
- WQRLCUGPDYKDFJ-IZHYLOQSSA-N ethyl (3z)-3-[[3-carbamoyl-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)=O)=C1 WQRLCUGPDYKDFJ-IZHYLOQSSA-N 0.000 description 1
- LMRDUCHWJWIOCU-RQZHXJHFSA-N ethyl (3z)-3-[[3-carbamoyl-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)=O)=C1 LMRDUCHWJWIOCU-RQZHXJHFSA-N 0.000 description 1
- GCYBFBVHWMONRI-IZHYLOQSSA-N ethyl (3z)-3-[[3-chloro-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(Cl)=C1 GCYBFBVHWMONRI-IZHYLOQSSA-N 0.000 description 1
- POPQNWNIUXXQCA-RQZHXJHFSA-N ethyl (3z)-3-[[3-chloro-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(Cl)=C1 POPQNWNIUXXQCA-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
- GYBLBBSLEFEACO-QPLCGJKRSA-N ethyl (3z)-3-[[4-(1,4-diaminobutyl)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=C1 GYBLBBSLEFEACO-QPLCGJKRSA-N 0.000 description 1
- CCUTYSBBHLIUID-IZHYLOQSSA-N ethyl (3z)-3-[[4-(1-amino-3-hydroxypropyl)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)CCO)C=C1 CCUTYSBBHLIUID-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
- QHJZOEGXPIGYLH-QPLCGJKRSA-N ethyl (3z)-3-[[4-(1-ethylimidazol-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=CN1CC QHJZOEGXPIGYLH-QPLCGJKRSA-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
- JPVQTOCCDAXLPQ-IZHYLOQSSA-N ethyl (3z)-3-[[4-(1h-imidazol-5-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=CNC=N1 JPVQTOCCDAXLPQ-IZHYLOQSSA-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
- WNKUPQSOZCOXPP-VHXPQNKSSA-N ethyl (3z)-3-[[4-(2-amino-2-oxoethyl)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(CC(N)=O)C=C1 WNKUPQSOZCOXPP-VHXPQNKSSA-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
- RUEIVCIJASUPPZ-IZHYLOQSSA-N ethyl (3z)-3-[[4-(3-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(CCCN)C=C1 RUEIVCIJASUPPZ-IZHYLOQSSA-N 0.000 description 1
- BSENHRCAKJZRCG-DQSJHHFOSA-N ethyl (3z)-3-[[4-(4-acetamido-1-aminobutyl)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)CCCNC(C)=O)C=C1 BSENHRCAKJZRCG-DQSJHHFOSA-N 0.000 description 1
- LRKHTNZONLERKV-RQZHXJHFSA-N ethyl (3z)-3-[[4-(4-methylpiperazin-1-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=C1N1CCN(C)CC1 LRKHTNZONLERKV-RQZHXJHFSA-N 0.000 description 1
- ABEYDRUXIUCZDP-LCUIJRPUSA-N ethyl (3z)-3-[[4-(5-methyl-1h-imidazol-4-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=C1C=1N=CNC=1C ABEYDRUXIUCZDP-LCUIJRPUSA-N 0.000 description 1
- YFOKAGGEUWYOAG-IZHYLOQSSA-N ethyl (3z)-3-[[4-(acetamidomethyl)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(C)=O)C=C1 YFOKAGGEUWYOAG-IZHYLOQSSA-N 0.000 description 1
- ZZRFQLQDQIIOEP-FCQUAONHSA-N ethyl (3z)-3-[[4-(aminomethyl)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=C1 ZZRFQLQDQIIOEP-FCQUAONHSA-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
- BGMCJJIINYTTBD-ZIADKAODSA-N ethyl (3z)-3-[[4-(azepan-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=C1CN1CCCCCC1 BGMCJJIINYTTBD-ZIADKAODSA-N 0.000 description 1
- XCQJIAXZZGZBHA-QPLCGJKRSA-N ethyl (3z)-3-[[4-(azetidin-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=C1CN1CCC1 XCQJIAXZZGZBHA-QPLCGJKRSA-N 0.000 description 1
- FREIEGMGSFYMRJ-RQZHXJHFSA-N ethyl (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)OCC)C=C2NC\1=O FREIEGMGSFYMRJ-RQZHXJHFSA-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
- XZMSFBYAWRFVKO-RQZHXJHFSA-N ethyl (3z)-3-[[4-(diethylaminomethyl)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(CC)CC)C=C1 XZMSFBYAWRFVKO-RQZHXJHFSA-N 0.000 description 1
- UAHPGQHLSDDKQC-IZHYLOQSSA-N ethyl (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)OCC)C=C2NC\1=O UAHPGQHLSDDKQC-IZHYLOQSSA-N 0.000 description 1
- CGJLGJPXRMRVDR-VHXPQNKSSA-N ethyl (3z)-3-[[4-(methanesulfonamidomethyl)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(CNS(C)(=O)=O)C=C1 CGJLGJPXRMRVDR-VHXPQNKSSA-N 0.000 description 1
- AGICOFWZEZEPSB-RQZHXJHFSA-N ethyl (3z)-3-[[4-(morpholin-4-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=C1CN1CCOCC1 AGICOFWZEZEPSB-RQZHXJHFSA-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
- DEAMOZKKDPGKEB-VHXPQNKSSA-N ethyl (3z)-3-[[4-[(2,5-dioxoimidazolidin-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=C1CC1NC(=O)NC1=O DEAMOZKKDPGKEB-VHXPQNKSSA-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
- MQKCTOHUDXGOFG-RQZHXJHFSA-N ethyl (3z)-3-[[4-[(2-acetamidoacetyl)-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)CNC(C)=O)C=C1 MQKCTOHUDXGOFG-RQZHXJHFSA-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
- 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 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
- ZFVWQYNIVJRCIG-KARKAFJISA-N ethyl (3z)-3-[[4-[(4-benzoylpiperazin-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=C1CN(CC1)CCN1C(=O)C1=CC=CC=C1 ZFVWQYNIVJRCIG-KARKAFJISA-N 0.000 description 1
- 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 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
- IDQUUVCPUPDESW-FLWNBWAVSA-N ethyl (3z)-3-[[4-[(benzylamino)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=C1CNCC1=CC=CC=C1 IDQUUVCPUPDESW-FLWNBWAVSA-N 0.000 description 1
- 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 1
- 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 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
- 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 1
- PLZZBWOORXREMY-QPLCGJKRSA-N ethyl (3z)-3-[[4-[(dimethylamino)methyl]-3-(methanesulfonamido)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(NS(C)(=O)=O)=C1 PLZZBWOORXREMY-QPLCGJKRSA-N 0.000 description 1
- 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 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
- 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 1
- YTQGMVPOQZVHPK-QPLCGJKRSA-N ethyl (3z)-3-[[4-[(dimethylamino)methyl]-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(CN(C)C)C(OC)=C1 YTQGMVPOQZVHPK-QPLCGJKRSA-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
- 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 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
- ACMBPOUTCUNNEI-QPLCGJKRSA-N ethyl (3z)-3-[[4-[1-amino-3-(methanesulfonamido)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)CCNS(C)(=O)=O)C=C1 ACMBPOUTCUNNEI-QPLCGJKRSA-N 0.000 description 1
- 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 1
- LPVZNMSLQKJADJ-RQZHXJHFSA-N ethyl (3z)-3-[[4-[1-amino-4-(methanesulfonamido)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)CCCNS(C)(=O)=O)C=C1 LPVZNMSLQKJADJ-RQZHXJHFSA-N 0.000 description 1
- 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 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
- JXRRPAMWMXLAIT-QPLCGJKRSA-N ethyl (3z)-3-[[4-[2-(dimethylamino)-2-oxoethyl]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(CC(=O)N(C)C)C=C1 JXRRPAMWMXLAIT-QPLCGJKRSA-N 0.000 description 1
- CASCEBAWSQINJU-QPLCGJKRSA-N ethyl (3z)-3-[[4-[2-(dimethylamino)ethoxy]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(OCCN(C)C)C=C1 CASCEBAWSQINJU-QPLCGJKRSA-N 0.000 description 1
- 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 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
- GXUGIZXHKDYVCY-YHZPTAEISA-N ethyl (3z)-3-[[4-[2-(dimethylamino)ethyl-(2-phenylacetyl)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)CC1=CC=CC=C1 GXUGIZXHKDYVCY-YHZPTAEISA-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
- VBFXBZFGKXGHNQ-KTMFPKCZSA-N ethyl (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)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1N(CCN(C)C)C(=O)C1=CC=CN=C1 VBFXBZFGKXGHNQ-KTMFPKCZSA-N 0.000 description 1
- RTTCGZGAJZHUIX-DQSJHHFOSA-N ethyl (3z)-3-[[4-[2-(dimethylamino)ethyl-ethylsulfonylamino]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)S(=O)(=O)CC)C=C1 RTTCGZGAJZHUIX-DQSJHHFOSA-N 0.000 description 1
- AYECMIXQKVZTGO-RQZHXJHFSA-N ethyl (3z)-3-[[4-[2-(dimethylamino)ethyl-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)CCN(C)C)C=C1 AYECMIXQKVZTGO-RQZHXJHFSA-N 0.000 description 1
- UCVDESGYVWSIKY-HKWRFOASSA-N ethyl (3z)-3-[[4-[2-(dimethylamino)ethyl-methylsulfonylamino]anilino]methylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C\NC1=CC=C(N(CCN(C)C)S(C)(=O)=O)C=C1 UCVDESGYVWSIKY-HKWRFOASSA-N 0.000 description 1
- UXEOJRZPJFJGEN-ZIADKAODSA-N ethyl (3z)-3-[[4-[2-(dimethylamino)ethyl-propan-2-ylsulfonylamino]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)S(=O)(=O)C(C)C)C=C1 UXEOJRZPJFJGEN-ZIADKAODSA-N 0.000 description 1
- DNCTTWJGVPDRGC-ZIADKAODSA-N ethyl (3z)-3-[[4-[2-(dimethylamino)ethyl-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(CCN(C)C)C(=O)CC)C=C1 DNCTTWJGVPDRGC-ZIADKAODSA-N 0.000 description 1
- GFSGTAGZIVWSAG-ZIADKAODSA-N ethyl (3z)-3-[[4-[2-(dimethylamino)ethyl-propylsulfonylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(CCN(C)C)S(=O)(=O)CCC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OCC)C=C2NC\1=O GFSGTAGZIVWSAG-ZIADKAODSA-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
- GBCXQHSGGVQQDS-RQZHXJHFSA-N ethyl (3z)-3-[[4-[2-(ethylamino)ethyl-methylsulfonylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(CCNCC)S(C)(=O)=O)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OCC)C=C2NC\1=O GBCXQHSGGVQQDS-RQZHXJHFSA-N 0.000 description 1
- DPAPEZMTLJUZFK-QPLCGJKRSA-N ethyl (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)OCC)C=C2NC\1=O DPAPEZMTLJUZFK-QPLCGJKRSA-N 0.000 description 1
- QJXWNVDUPLASNH-QPLCGJKRSA-N ethyl (3z)-3-[[4-[2-(methylamino)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(CCNC)S(C)(=O)=O)C=C1 QJXWNVDUPLASNH-QPLCGJKRSA-N 0.000 description 1
- 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 1
- YQQJLSHQMXFNGJ-KARKAFJISA-N ethyl (3z)-3-[[4-[2-[benzyl(methyl)amino]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)\NC(C=C1)=CC=C1N(S(C)(=O)=O)CCN(C)CC1=CC=CC=C1 YQQJLSHQMXFNGJ-KARKAFJISA-N 0.000 description 1
- 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 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
- 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 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
- SGYQUGCRXMGSLV-DQSJHHFOSA-N ethyl (3z)-3-[[4-[3-(dimethylamino)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(C)C)C=C1 SGYQUGCRXMGSLV-DQSJHHFOSA-N 0.000 description 1
- GMMCUXSRHGXTGE-FLWNBWAVSA-N ethyl (3z)-3-[[4-[3-(dimethylamino)propanoyl-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)CCN(C)C)C=C1 GMMCUXSRHGXTGE-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
- YHIXYTDHADFYNE-DQSJHHFOSA-N ethyl (3z)-3-[[4-[3-(dimethylamino)propyl-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(CCCN(C)C)S(C)(=O)=O)C=C1 YHIXYTDHADFYNE-DQSJHHFOSA-N 0.000 description 1
- GOBHWFVVQJHNIB-RQZHXJHFSA-N ethyl (3z)-3-[[4-[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(CCCN(C)C)C=C1 GOBHWFVVQJHNIB-RQZHXJHFSA-N 0.000 description 1
- USJLMERHOSFDGH-RQZHXJHFSA-N ethyl (3z)-3-[[4-[3-(methylamino)propyl-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(CCCNC)S(C)(=O)=O)C=C1 USJLMERHOSFDGH-RQZHXJHFSA-N 0.000 description 1
- JZGMCNWSYULLGN-YHZPTAEISA-N ethyl (3z)-3-[[4-[3-[benzyl(methyl)amino]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)\NC(C=C1)=CC=C1N(C)C(=O)CCN(C)CC1=CC=CC=C1 JZGMCNWSYULLGN-YHZPTAEISA-N 0.000 description 1
- LHYMDCLMWFYNAO-YHZPTAEISA-N ethyl (3z)-3-[[4-[3-[benzyl(methyl)amino]propyl-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)\NC(C=C1)=CC=C1N(S(C)(=O)=O)CCCN(C)CC1=CC=CC=C1 LHYMDCLMWFYNAO-YHZPTAEISA-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
- QILYYCRNPGJUOB-MVJHLKBCSA-N ethyl (3z)-3-[[4-[4-(dimethylamino)butanoyl-[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(=O)CCCN(C)C)C=C1 QILYYCRNPGJUOB-MVJHLKBCSA-N 0.000 description 1
- YVFLJBZTBGIMCY-QPLCGJKRSA-N ethyl (3z)-3-[[4-[[(2-amino-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(N)=O)C=C1 YVFLJBZTBGIMCY-QPLCGJKRSA-N 0.000 description 1
- KPLNAMNDLNVERF-DQSJHHFOSA-N ethyl (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)OCC)C=C2NC\1=O KPLNAMNDLNVERF-DQSJHHFOSA-N 0.000 description 1
- BLZAOVRTMUHFRB-DQSJHHFOSA-N ethyl (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)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CN(C)CC1OCCO1 BLZAOVRTMUHFRB-DQSJHHFOSA-N 0.000 description 1
- YDXNTWYCMIOZIR-ZIADKAODSA-N ethyl (3z)-3-[[4-[[2-(2-methoxyethoxy)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)CCOCCOC)C=C1 YDXNTWYCMIOZIR-ZIADKAODSA-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
- RZFGCSNHFMPVGN-ZIADKAODSA-N ethyl (3z)-3-[[4-[[2-(diethylamino)-2-oxoethyl]-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(CC(=O)N(CC)CC)S(C)(=O)=O)C=C1 RZFGCSNHFMPVGN-ZIADKAODSA-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
- AOCLJRYSPLWGNW-KTMFPKCZSA-N ethyl (3z)-3-[[4-[[2-(dimethylamino)-2-oxoethyl]-[3-(dimethylamino)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(CC(=O)N(C)C)C(=O)CCN(C)C)C=C1 AOCLJRYSPLWGNW-KTMFPKCZSA-N 0.000 description 1
- 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 1
- UNBQUTRCPHSDIA-RQZHXJHFSA-N ethyl (3z)-3-[[4-[[2-(dimethylamino)-2-oxoethyl]-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(CC(=O)N(C)C)S(C)(=O)=O)C=C1 UNBQUTRCPHSDIA-RQZHXJHFSA-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
- 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 1
- KQNBTRPFVVQLRT-DQSJHHFOSA-N ethyl (3z)-3-[[4-[[2-(dimethylamino)acetyl]-methylamino]-3-(methanesulfonamido)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(NS(C)(=O)=O)=C1 KQNBTRPFVVQLRT-DQSJHHFOSA-N 0.000 description 1
- 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 1
- HUJGOHAHCWRDTA-ZIADKAODSA-N ethyl (3z)-3-[[4-[[2-(dimethylamino)acetyl]-methylamino]-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(N(C)C(=O)CN(C)C)C(C(=O)OCC)=C1 HUJGOHAHCWRDTA-ZIADKAODSA-N 0.000 description 1
- FWVNYIJGAKFLPG-RQZHXJHFSA-N ethyl (3z)-3-[[4-[[2-(dimethylamino)acetyl]-methylamino]-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(N(C)C(=O)CN(C)C)C(F)=C1 FWVNYIJGAKFLPG-RQZHXJHFSA-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
- 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 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
- 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 1
- SWRUJBCJOYDYCW-RQZHXJHFSA-N ethyl (3z)-3-[[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=C1 SWRUJBCJOYDYCW-RQZHXJHFSA-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
- BQPHHPYJKHHELN-RQZHXJHFSA-N ethyl (3z)-3-[[4-[[2-(ethylamino)-2-oxoethyl]-methylsulfonylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(CC(=O)NCC)S(C)(=O)=O)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OCC)C=C2NC\1=O BQPHHPYJKHHELN-RQZHXJHFSA-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
- NGDNHJZYQZUQFE-QPLCGJKRSA-N ethyl (3z)-3-[[4-[[2-(methanesulfonamido)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)CNS(C)(=O)=O)C=C1 NGDNHJZYQZUQFE-QPLCGJKRSA-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
- PFLKOMYHOCHLSW-QPLCGJKRSA-N ethyl (3z)-3-[[4-[[2-(methylamino)-2-oxoethyl]-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(CC(=O)NC)S(C)(=O)=O)C=C1 PFLKOMYHOCHLSW-QPLCGJKRSA-N 0.000 description 1
- 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 1
- 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 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
- UNCJGAFZCSMCFF-KARKAFJISA-N ethyl (3z)-3-[[4-[[2-[benzyl(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)\NC(C=C1)=CC=C1N(C)C(=O)CN(C)CC1=CC=CC=C1 UNCJGAFZCSMCFF-KARKAFJISA-N 0.000 description 1
- UOTYYZPXQGKBHV-ZIADKAODSA-N ethyl (3z)-3-[[4-[[2-[bis(2-hydroxyethyl)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(CCO)CCO)C=C1 UOTYYZPXQGKBHV-ZIADKAODSA-N 0.000 description 1
- LTURZOBDFIRNPQ-DQSJHHFOSA-N ethyl (3z)-3-[[4-[[2-acetamidoethyl(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)CCNC(C)=O)C=C1 LTURZOBDFIRNPQ-DQSJHHFOSA-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
- 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 1
- COIPPHYWTDFRLX-QPLCGJKRSA-N ethyl (3z)-3-[[4-[[2-hydroxyethyl(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)CCO)C=C1 COIPPHYWTDFRLX-QPLCGJKRSA-N 0.000 description 1
- 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 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
- RJRHDEDVWGYZCX-DQSJHHFOSA-N ethyl (3z)-3-[[4-[[3-(methanesulfonamido)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)CCCNS(C)(=O)=O)C=C1 RJRHDEDVWGYZCX-DQSJHHFOSA-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
- JQNBDJDJCAUYAS-RQZHXJHFSA-N ethyl (3z)-3-[[4-[[3-aminopropyl(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)CCCN)C=C1 JQNBDJDJCAUYAS-RQZHXJHFSA-N 0.000 description 1
- JTLUINUGLRLOCP-ZIADKAODSA-N ethyl (3z)-3-[[4-[[4-(hydroxymethyl)piperidin-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(CO)CC1 JTLUINUGLRLOCP-ZIADKAODSA-N 0.000 description 1
- 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 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
- 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 1
- 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 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
- XWXIDGHFZIVFOM-ZIADKAODSA-N ethyl (3z)-3-[[4-[[di(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)C)C=C1 XWXIDGHFZIVFOM-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
- QYHBEJPCAKKSLL-DQSJHHFOSA-N ethyl (3z)-3-[[4-[[ethyl(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(CC)C(C)C)C=C1 QYHBEJPCAKKSLL-DQSJHHFOSA-N 0.000 description 1
- 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 1
- ZQWXMEXHUFYHHO-FLWNBWAVSA-N ethyl (3z)-3-[[4-[[hexyl(methyl)amino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(CN(C)CCCCCC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OCC)C=C2NC\1=O ZQWXMEXHUFYHHO-FLWNBWAVSA-N 0.000 description 1
- 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 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
- 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 1
- 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 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
- 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 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
- 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 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
- RJUIYXJUPRCXAC-RQZHXJHFSA-N ethyl (3z)-3-[[4-[acetyl-[2-(methylamino)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)\NC1=CC=C(N(CCNC)C(C)=O)C=C1 RJUIYXJUPRCXAC-RQZHXJHFSA-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
- 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 1
- TULSWGWWDPGLOB-MVJHLKBCSA-N ethyl (3z)-3-[[4-[benzenesulfonyl-[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)S(=O)(=O)C1=CC=CC=C1 TULSWGWWDPGLOB-MVJHLKBCSA-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
- VHKIRFYNQMUMSF-KXYMVQBMSA-N ethyl (3z)-3-[[4-[benzyl-(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(=O)CN1CCCCC1)CC1=CC=CC=C1 VHKIRFYNQMUMSF-KXYMVQBMSA-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
- KVCAVTPMCICCGL-OKULSNQLSA-N ethyl (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)OCC)=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 KVCAVTPMCICCGL-OKULSNQLSA-N 0.000 description 1
- AJKUNZUXLYDJFT-YHZPTAEISA-N ethyl (3z)-3-[[4-[benzyl-[3-(dimethylamino)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)\NC(C=C1)=CC=C1N(C(=O)CCN(C)C)CC1=CC=CC=C1 AJKUNZUXLYDJFT-YHZPTAEISA-N 0.000 description 1
- GKBUIXVCHMKVHT-KARKAFJISA-N ethyl (3z)-3-[[4-[benzylsulfonyl-[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)S(=O)(=O)CC1=CC=CC=C1 GKBUIXVCHMKVHT-KARKAFJISA-N 0.000 description 1
- WWDQJUBVYPICKX-FLWNBWAVSA-N ethyl (3z)-3-[[4-[butanoyl-[2-(dimethylamino)ethyl]amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(CCN(C)C)C(=O)CCC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OCC)C=C2NC\1=O WWDQJUBVYPICKX-FLWNBWAVSA-N 0.000 description 1
- LSHUSAIZNQKPAS-FLWNBWAVSA-N ethyl (3z)-3-[[4-[butylsulfonyl-[2-(dimethylamino)ethyl]amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(CCN(C)C)S(=O)(=O)CCCC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OCC)C=C2NC\1=O LSHUSAIZNQKPAS-FLWNBWAVSA-N 0.000 description 1
- AVTNJZHIJVLNJD-FCQUAONHSA-N ethyl (3z)-3-[[4-[carbamoyl(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(N)=O)C=C1 AVTNJZHIJVLNJD-FCQUAONHSA-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
- PAPUNFNBPRWXLG-IZHYLOQSSA-N ethyl (3z)-3-[[4-[dimethylcarbamoyl(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)N(C)C)C=C1 PAPUNFNBPRWXLG-IZHYLOQSSA-N 0.000 description 1
- VSHSTIOQSJOABU-FLWNBWAVSA-N ethyl (3z)-3-[[4-[methyl(3-piperazin-1-ylpropanoyl)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)CCN1CCNCC1 VSHSTIOQSJOABU-FLWNBWAVSA-N 0.000 description 1
- VKSLIISTSUYJNY-KTMFPKCZSA-N ethyl (3z)-3-[[4-[methyl(3-piperidin-1-ylpropanoyl)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 VKSLIISTSUYJNY-KTMFPKCZSA-N 0.000 description 1
- 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 1
- QQNSZOYLODFTDA-VHXPQNKSSA-N ethyl (3z)-3-[[4-[methyl(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(C)S(C)(=O)=O)C=C1 QQNSZOYLODFTDA-VHXPQNKSSA-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
- IDUOPIZEQCZLER-ZIADKAODSA-N ethyl (3z)-3-[[4-[methyl-(2-morpholin-4-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)CN1CCOCC1 IDUOPIZEQCZLER-ZIADKAODSA-N 0.000 description 1
- 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 1
- ULLAZJHMOYMAMV-ZIADKAODSA-N ethyl (3z)-3-[[4-[methyl-(2-pyrrolidin-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)CN1CCCC1 ULLAZJHMOYMAMV-ZIADKAODSA-N 0.000 description 1
- 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 1
- QHKHFJPYEGJCLF-QPLCGJKRSA-N ethyl (3z)-3-[[4-[methyl-[2-(methylamino)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)\NC1=CC=C(N(C)C(=O)CNC)C=C1 QHKHFJPYEGJCLF-QPLCGJKRSA-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
- JLUSNLJHTYLJRZ-ZIADKAODSA-N ethyl (3z)-3-[[4-[methylsulfonyl(2-morpholin-4-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(S(C)(=O)=O)CCN1CCOCC1 JLUSNLJHTYLJRZ-ZIADKAODSA-N 0.000 description 1
- PEJDTEHJOQHUCK-ZIADKAODSA-N ethyl (3z)-3-[[4-[methylsulfonyl(2-piperazin-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(S(C)(=O)=O)CCN1CCNCC1 PEJDTEHJOQHUCK-ZIADKAODSA-N 0.000 description 1
- SAAUOARNQLDUED-FLWNBWAVSA-N ethyl (3z)-3-[[4-[methylsulfonyl(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(S(C)(=O)=O)CCN1CCCCC1 SAAUOARNQLDUED-FLWNBWAVSA-N 0.000 description 1
- PKBMKCUECQFMQK-ZIADKAODSA-N ethyl (3z)-3-[[4-[methylsulfonyl(2-pyrrolidin-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(S(C)(=O)=O)CCN1CCCC1 PKBMKCUECQFMQK-ZIADKAODSA-N 0.000 description 1
- SONLWORPDRBPQU-ZIADKAODSA-N ethyl (3z)-3-[[4-[methylsulfonyl-(2-morpholin-4-yl-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)\NC(C=C1)=CC=C1N(S(C)(=O)=O)CC(=O)N1CCOCC1 SONLWORPDRBPQU-ZIADKAODSA-N 0.000 description 1
- MLFXRMNOAMCOIN-ZIADKAODSA-N ethyl (3z)-3-[[4-[methylsulfonyl-(2-oxo-2-piperazin-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(S(C)(=O)=O)CC(=O)N1CCNCC1 MLFXRMNOAMCOIN-ZIADKAODSA-N 0.000 description 1
- WCMFSXLIJQAIHZ-FLWNBWAVSA-N ethyl (3z)-3-[[4-[methylsulfonyl-(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(S(C)(=O)=O)CC(=O)N1CCCCC1 WCMFSXLIJQAIHZ-FLWNBWAVSA-N 0.000 description 1
- DBHMCCIITPMTLJ-ZIADKAODSA-N ethyl (3z)-3-[[4-[methylsulfonyl-(2-oxo-2-pyrrolidin-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(S(C)(=O)=O)CC(=O)N1CCCC1 DBHMCCIITPMTLJ-ZIADKAODSA-N 0.000 description 1
- OYHYOARTJMKBTC-QPLCGJKRSA-N ethyl (3z)-3-[[4-[methylsulfonyl-[3-[(2,2,2-trifluoroacetyl)amino]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(CCCNC(=O)C(F)(F)F)S(C)(=O)=O)C=C1 OYHYOARTJMKBTC-QPLCGJKRSA-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
- 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
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
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- 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
- 125000002541 furyl group Chemical group 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
- 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
- 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
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- 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
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- WZHJKEUHNJHDLS-QTGUNEKASA-N metergoline Chemical compound C([C@H]1CN([C@H]2[C@@H](C=3C=CC=C4N(C)C=C(C=34)C2)C1)C)NC(=O)OCC1=CC=CC=C1 WZHJKEUHNJHDLS-QTGUNEKASA-N 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- NWGFZRMUBODUET-DIBXZPPDSA-N methyl (3z)-2-oxo-3-[1-[4-(1,2,4,5-tetrahydro-3-benzazepin-3-ylmethyl)anilino]ethylidene]-1h-indole-6-carboxylate Chemical compound C1CC2=CC=CC=C2CCN1CC(C=C1)=CC=C1NC(/C)=C1/C2=CC=C(C(=O)OC)C=C2NC1=O NWGFZRMUBODUET-DIBXZPPDSA-N 0.000 description 1
- 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 1
- UATXNAGHLAANAB-YBEGLDIGSA-N methyl (3z)-2-oxo-3-[1-[4-(2h-tetrazol-5-yl)anilino]ethylidene]-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(/C)NC(C=C1)=CC=C1C1=NN=NN1 UATXNAGHLAANAB-YBEGLDIGSA-N 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
- 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 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
- 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 1
- LNJSJWOCLRJVIA-ZHZULCJRSA-N methyl (3z)-2-oxo-3-[[4-(piperidin-1-ylmethyl)anilino]methylidene]-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C\NC(C=C1)=CC=C1CN1CCCCC1 LNJSJWOCLRJVIA-ZHZULCJRSA-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
- 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 1
- 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 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
- PHIGDVCYFZLICL-VHXPQNKSSA-N methyl (3z)-2-oxo-3-[phenyl-[4-(1,2,4-triazol-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=C1CN1C=NC=N1 PHIGDVCYFZLICL-VHXPQNKSSA-N 0.000 description 1
- 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 1
- 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 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
- 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
- WIBHRANONYESRM-RQZHXJHFSA-N methyl (3z)-2-oxo-3-[phenyl-[4-(pyridin-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=C1CC1=CC=NC=C1 WIBHRANONYESRM-RQZHXJHFSA-N 0.000 description 1
- SKQVWHWWKSQUPK-QPLCGJKRSA-N methyl (3z)-2-oxo-3-[phenyl-[4-(pyrrolidin-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=C1CN1CCCC1 SKQVWHWWKSQUPK-QPLCGJKRSA-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
- BTAQJYBUIQPDQB-VHXPQNKSSA-N methyl (3z)-2-oxo-3-[phenyl-[4-(triazol-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=C1CN1C=CN=N1 BTAQJYBUIQPDQB-VHXPQNKSSA-N 0.000 description 1
- 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 1
- 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 1
- YMDHFSHAFSDHGC-FLWNBWAVSA-N methyl (3z)-2-oxo-3-[phenyl-[4-[(2-piperazin-1-ylacetyl)-propan-2-ylamino]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=C1N(C(C)C)C(=O)CN1CCNCC1 YMDHFSHAFSDHGC-FLWNBWAVSA-N 0.000 description 1
- IIIGSXYVAHIXRD-KTMFPKCZSA-N methyl (3z)-2-oxo-3-[phenyl-[4-[(2-piperidin-1-ylacetyl)-propan-2-ylamino]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=C1N(C(C)C)C(=O)CN1CCCCC1 IIIGSXYVAHIXRD-KTMFPKCZSA-N 0.000 description 1
- 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 1
- 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 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
- 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 1
- NQROFBRJNJSXKA-DQRAZIAOSA-N methyl (3z)-3-[(4-cyanoanilino)-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)C=C1 NQROFBRJNJSXKA-DQRAZIAOSA-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
- 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 1
- 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 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
- NIGSGKHDAXWGET-DQRAZIAOSA-N methyl (3z)-3-[(4-methylsulfanylanilino)-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(SC)C=C1 NIGSGKHDAXWGET-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
- 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 1
- KTMRGGRJYLKBHD-UYRXBGFRSA-N methyl (3z)-3-[1-[4-[(dimethylamino)methyl]anilino]ethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(/C)NC1=CC=C(CN(C)C)C=C1 KTMRGGRJYLKBHD-UYRXBGFRSA-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
- XLATZSOYBAIVBD-LNVKXUELSA-N methyl (3z)-3-[1-[4-[2-(dimethylamino)ethyl-methylsulfonylamino]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(CCN(C)C)S(C)(=O)=O)C=C1 XLATZSOYBAIVBD-LNVKXUELSA-N 0.000 description 1
- FGKCDZDCSVOVDJ-QNGOZBTKSA-N methyl (3z)-3-[1-[4-[2-(dimethylamino)ethyl-methylsulfonylamino]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(CCN(C)C)S(C)(=O)=O)C=C1 FGKCDZDCSVOVDJ-QNGOZBTKSA-N 0.000 description 1
- NKVHDFUOFRWEAU-XDOYNYLZSA-N methyl (3z)-3-[1-[4-[2-(dimethylamino)ethyl-methylsulfonylamino]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(CCN(C)C)S(C)(=O)=O)C=C1 NKVHDFUOFRWEAU-XDOYNYLZSA-N 0.000 description 1
- GAUGECNRBWBZTG-XYGWBWBKSA-N methyl (3z)-3-[1-[4-[2-amino-1-(1,3-benzodioxol-5-yl)propan-2-yl]anilino]ethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=C2OCOC2=CC(CC(C)(N)C2=CC=C(C=C2)NC(/C)=C2/C3=CC=C(C=C3NC2=O)C(=O)OC)=C1 GAUGECNRBWBZTG-XYGWBWBKSA-N 0.000 description 1
- YKHIDKWUYMOXDT-IMRQLAEWSA-N methyl (3z)-3-[1-[4-[[(3,4-dimethoxyphenyl)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(OC)C(OC)=C1 YKHIDKWUYMOXDT-IMRQLAEWSA-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
- IYEXORZJYRDEFY-UQQQWYQISA-N methyl (3z)-3-[1-[4-[[(4-fluorophenyl)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(F)C=C1 IYEXORZJYRDEFY-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
- 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 1
- 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 1
- 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 1
- 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 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
- 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 1
- FCLITXSPSUOHHD-VHXPQNKSSA-N methyl (3z)-3-[[3,5-dibromo-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(Br)=C(CN(C)C)C(Br)=C1 FCLITXSPSUOHHD-VHXPQNKSSA-N 0.000 description 1
- SNUSQQNGMPGWRB-IZHYLOQSSA-N methyl (3z)-3-[[3,5-dibromo-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(Br)=C(N(C)C(=O)CN(C)C)C(Br)=C1 SNUSQQNGMPGWRB-IZHYLOQSSA-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
- WHGUKMHPXLLKDE-ZIADKAODSA-N methyl (3z)-3-[[3-(3-ethoxy-3-oxopropyl)phenyl]-[4-(1-methylimidazol-2-yl)anilino]methylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound CCOC(=O)CCC1=CC=CC(C(\NC=2C=CC(=CC=2)C=2N(C=CN=2)C)=C\2C3=CC=C(C=C3NC/2=O)C(=O)OC)=C1 WHGUKMHPXLLKDE-ZIADKAODSA-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
- GJZOCJMBIIKQIK-DQSJHHFOSA-N methyl (3z)-3-[[3-acetamido-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(NC(C)=O)=C1 GJZOCJMBIIKQIK-DQSJHHFOSA-N 0.000 description 1
- 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 1
- FQPQINWPSPWZJS-QPLCGJKRSA-N methyl (3z)-3-[[3-amino-4-[2-(dimethylamino)ethyl-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(CCN(C)C)S(C)(=O)=O)C(N)=C1 FQPQINWPSPWZJS-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
- 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 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
- 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 1
- PYWYMRSZOWDEDS-QPLCGJKRSA-N methyl (3z)-3-[[3-chloro-4-[2-(dimethylamino)ethyl-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(CCN(C)C)S(C)(=O)=O)C(Cl)=C1 PYWYMRSZOWDEDS-QPLCGJKRSA-N 0.000 description 1
- 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 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
- 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
- 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 1
- SWAVLWARVHHEJM-QPLCGJKRSA-N methyl (3z)-3-[[4-(1-amino-3-ethoxy-3-oxopropyl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(C(N)CC(=O)OCC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O SWAVLWARVHHEJM-QPLCGJKRSA-N 0.000 description 1
- 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 1
- YAPOARLAMRUWED-IZHYLOQSSA-N methyl (3z)-3-[[4-(1-amino-3-methoxypropyl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(C(N)CCOC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O YAPOARLAMRUWED-IZHYLOQSSA-N 0.000 description 1
- 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 1
- QRYXUASSWIFHFW-IZHYLOQSSA-N methyl (3z)-3-[[4-(1-ethylimidazol-2-yl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound CCN1C=CN=C1C(C=C1)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O QRYXUASSWIFHFW-IZHYLOQSSA-N 0.000 description 1
- 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 1
- QYUVQENLWCRKLV-VHXPQNKSSA-N methyl (3z)-3-[[4-(1h-imidazol-5-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=CNC=N1 QYUVQENLWCRKLV-VHXPQNKSSA-N 0.000 description 1
- 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 1
- FSZGHRMXKHMOCA-IZHYLOQSSA-N methyl (3z)-3-[[4-(2-acetamidoethyl)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(CCNC(C)=O)C=C1 FSZGHRMXKHMOCA-IZHYLOQSSA-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
- 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 1
- FOZZNPZXSKJEQN-DQSJHHFOSA-N methyl (3z)-3-[[4-(anilinomethyl)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=C1CNC1=CC=CC=C1 FOZZNPZXSKJEQN-DQSJHHFOSA-N 0.000 description 1
- LAVIABVORHCAAD-DQSJHHFOSA-N methyl (3z)-3-[[4-(azepan-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=C1CN1CCCCCC1 LAVIABVORHCAAD-DQSJHHFOSA-N 0.000 description 1
- GKJAQZQLIADODD-IZHYLOQSSA-N methyl (3z)-3-[[4-(azetidin-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=C1CN1CCC1 GKJAQZQLIADODD-IZHYLOQSSA-N 0.000 description 1
- 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 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
- 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 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
- 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 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
- 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 1
- 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 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
- XBUCECOAKVVLNR-ZIADKAODSA-N methyl (3z)-3-[[4-[(2,6-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=C1CN1C(C)CCCC1C XBUCECOAKVVLNR-ZIADKAODSA-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
- 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
- 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 1
- JOJRRLVBVACGHK-QPLCGJKRSA-N methyl (3z)-3-[[4-[(3-hydroxypyrrolidin-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(O)C1 JOJRRLVBVACGHK-QPLCGJKRSA-N 0.000 description 1
- DWQMEXHZENVEEZ-RQZHXJHFSA-N methyl (3z)-3-[[4-[(4-hydroxypiperidin-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(O)CC1 DWQMEXHZENVEEZ-RQZHXJHFSA-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
- 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 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
- 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 1
- 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 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
- 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 1
- 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 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
- 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 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
- NQFDXCBVWXJEFE-IZHYLOQSSA-N methyl (3z)-3-[[4-[(dimethylamino)methyl]-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(CN(C)C)C(C)=C1 NQFDXCBVWXJEFE-IZHYLOQSSA-N 0.000 description 1
- HHKBMUPUGVPVTO-VHXPQNKSSA-N methyl (3z)-3-[[4-[(dimethylamino)methyl]-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(CN(C)C)C([N+]([O-])=O)=C1 HHKBMUPUGVPVTO-VHXPQNKSSA-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
- JSMNAIQZPHZGCP-DQSJHHFOSA-N methyl (3z)-3-[[4-[(dimethylamino)methyl]anilino]-[4-(3-methoxy-3-oxopropyl)phenyl]methylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C(\NC=1C=CC(CN(C)C)=CC=1)=C\1C2=CC=C(C(=O)OC)C=C2NC/1=O JSMNAIQZPHZGCP-DQSJHHFOSA-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
- 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 1
- 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 1
- BTHGXGDWQASQRP-RQZHXJHFSA-N methyl (3z)-3-[[4-[1-amino-4-(dimethylamino)butyl]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)C)C=C1 BTHGXGDWQASQRP-RQZHXJHFSA-N 0.000 description 1
- VWANDBSUBUHNFW-QPLCGJKRSA-N methyl (3z)-3-[[4-[1-amino-4-(methanesulfonamido)butyl]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)CCCNS(C)(=O)=O)C=C1 VWANDBSUBUHNFW-QPLCGJKRSA-N 0.000 description 1
- 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 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
- ZBGGFGDKVXCEJA-DQSJHHFOSA-N methyl (3z)-3-[[4-[2-(diethylamino)ethyl-methylsulfonylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(CCN(CC)CC)S(C)(=O)=O)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O ZBGGFGDKVXCEJA-DQSJHHFOSA-N 0.000 description 1
- HMOGURSRJGPJER-RQZHXJHFSA-N methyl (3z)-3-[[4-[2-(diethylamino)ethyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(CCN(CC)CC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O HMOGURSRJGPJER-RQZHXJHFSA-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
- CSNFJPOWLKGLBC-DQSJHHFOSA-N methyl (3z)-3-[[4-[2-(dimethylamino)ethyl-(2-methylpropanoyl)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(=O)C(C)C)C=C1 CSNFJPOWLKGLBC-DQSJHHFOSA-N 0.000 description 1
- NSEGQXXOKNFRQH-KARKAFJISA-N methyl (3z)-3-[[4-[2-(dimethylamino)ethyl-(2-phenylacetyl)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)CC1=CC=CC=C1 NSEGQXXOKNFRQH-KARKAFJISA-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
- 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 1
- UTISDSYHQVSJSO-RQZHXJHFSA-N methyl (3z)-3-[[4-[2-(dimethylamino)ethyl-ethylsulfonylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(CCN(C)C)S(=O)(=O)CC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O UTISDSYHQVSJSO-RQZHXJHFSA-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
- FRMJERXCKVFNHH-QPLCGJKRSA-N methyl (3z)-3-[[4-[2-(dimethylamino)ethyl-methylsulfonylamino]-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(CCN(C)C)S(C)(=O)=O)C([N+]([O-])=O)=C1 FRMJERXCKVFNHH-QPLCGJKRSA-N 0.000 description 1
- IOFQDWWCXFTDHF-RGEXLXHISA-N methyl (3z)-3-[[4-[2-(dimethylamino)ethyl-methylsulfonylamino]anilino]methylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C\NC1=CC=C(N(CCN(C)C)S(C)(=O)=O)C=C1 IOFQDWWCXFTDHF-RGEXLXHISA-N 0.000 description 1
- QPLOMASLTXFSGF-DQSJHHFOSA-N methyl (3z)-3-[[4-[2-(dimethylamino)ethyl-propan-2-ylsulfonylamino]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)S(=O)(=O)C(C)C)C=C1 QPLOMASLTXFSGF-DQSJHHFOSA-N 0.000 description 1
- 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 1
- AGQVXLYIQBWXIE-DQSJHHFOSA-N methyl (3z)-3-[[4-[2-(dimethylamino)ethyl-propylsulfonylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(CCN(C)C)S(=O)(=O)CCC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O AGQVXLYIQBWXIE-DQSJHHFOSA-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
- 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 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
- XNJPIGSAHQKNRZ-QPLCGJKRSA-N methyl (3z)-3-[[4-[2-(ethylamino)ethyl-methylsulfonylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(CCNCC)S(C)(=O)=O)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O XNJPIGSAHQKNRZ-QPLCGJKRSA-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
- 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 1
- AFUJQLGSXUWNHA-MVJHLKBCSA-N methyl (3z)-3-[[4-[2-[benzyl(methyl)amino]ethyl-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)\NC(C=C1)=CC=C1N(S(C)(=O)=O)CCN(C)CC1=CC=CC=C1 AFUJQLGSXUWNHA-MVJHLKBCSA-N 0.000 description 1
- MXFOZFBVTXOVHM-ZIADKAODSA-N methyl (3z)-3-[[4-[3-(diethylamino)propanoyl-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(C)C(=O)CCN(CC)CC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O MXFOZFBVTXOVHM-ZIADKAODSA-N 0.000 description 1
- UWEUSLXHJVTPRO-ZIADKAODSA-N methyl (3z)-3-[[4-[3-(dimethylamino)propanoyl-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)CCN(C)C)C=C1 UWEUSLXHJVTPRO-ZIADKAODSA-N 0.000 description 1
- 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 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
- 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 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
- DPKXPQRIMHPSDV-KARKAFJISA-N methyl (3z)-3-[[4-[3-[benzyl(methyl)amino]propyl-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)\NC(C=C1)=CC=C1N(S(C)(=O)=O)CCCN(C)CC1=CC=CC=C1 DPKXPQRIMHPSDV-KARKAFJISA-N 0.000 description 1
- 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 1
- AOZQUABEISRQBJ-KTMFPKCZSA-N methyl (3z)-3-[[4-[4-(dimethylamino)butanoyl-[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(=O)CCCN(C)C)C=C1 AOZQUABEISRQBJ-KTMFPKCZSA-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
- 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 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
- BTUACWQNCVFDMG-DQSJHHFOSA-N methyl (3z)-3-[[4-[[2-(diethylamino)-2-oxoethyl]-methylsulfonylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(CC(=O)N(CC)CC)S(C)(=O)=O)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O BTUACWQNCVFDMG-DQSJHHFOSA-N 0.000 description 1
- 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 1
- ILECHYCXOGCREG-FLWNBWAVSA-N methyl (3z)-3-[[4-[[2-(dimethylamino)-2-oxoethyl]-[3-(dimethylamino)propanoyl]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(=O)CCN(C)C)C=C1 ILECHYCXOGCREG-FLWNBWAVSA-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
- 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 1
- 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 1
- VJLJKPGFMIFONZ-RQZHXJHFSA-N methyl (3z)-3-[[4-[[2-(dimethylamino)acetyl]-ethylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(C(=O)CN(C)C)CC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O VJLJKPGFMIFONZ-RQZHXJHFSA-N 0.000 description 1
- HOXJEHKBYSZHDT-RQZHXJHFSA-N methyl (3z)-3-[[4-[[2-(dimethylamino)acetyl]-methylamino]-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(N(C)C(=O)CN(C)C)C(NS(C)(=O)=O)=C1 HOXJEHKBYSZHDT-RQZHXJHFSA-N 0.000 description 1
- KJSDEBDEMNRIHV-QPLCGJKRSA-N methyl (3z)-3-[[4-[[2-(dimethylamino)acetyl]-methylamino]-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(N(C)C(=O)CN(C)C)C(C(F)(F)F)=C1 KJSDEBDEMNRIHV-QPLCGJKRSA-N 0.000 description 1
- ZWTAJWPLJCTCQP-DQSJHHFOSA-N methyl (3z)-3-[[4-[[2-(dimethylamino)acetyl]-methylamino]-3-ethoxycarbonylanilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=C(N(C)C(=O)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 ZWTAJWPLJCTCQP-DQSJHHFOSA-N 0.000 description 1
- WAUCSJCPUORSTC-QPLCGJKRSA-N methyl (3z)-3-[[4-[[2-(dimethylamino)acetyl]-methylamino]-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(N(C)C(=O)CN(C)C)C(F)=C1 WAUCSJCPUORSTC-QPLCGJKRSA-N 0.000 description 1
- 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 1
- 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 1
- 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 1
- 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 1
- FVQJAAAWWIGEMK-DQSJHHFOSA-N methyl (3z)-3-[[4-[[2-(dimethylamino)acetyl]-propylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(C(=O)CN(C)C)CCC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O FVQJAAAWWIGEMK-DQSJHHFOSA-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
- CVVUEFYQDKDCGX-FLWNBWAVSA-N methyl (3z)-3-[[4-[[2-(dipropylamino)acetyl]-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(C)C(=O)CN(CCC)CCC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O CVVUEFYQDKDCGX-FLWNBWAVSA-N 0.000 description 1
- CXDYWQZLHPBBQY-QPLCGJKRSA-N methyl (3z)-3-[[4-[[2-(ethylamino)-2-oxoethyl]-methylsulfonylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(CC(=O)NCC)S(C)(=O)=O)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O CXDYWQZLHPBBQY-QPLCGJKRSA-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
- RTXFTXQHTXRSSM-IZHYLOQSSA-N methyl (3z)-3-[[4-[[2-(methanesulfonamido)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)CNS(C)(=O)=O)C=C1 RTXFTXQHTXRSSM-IZHYLOQSSA-N 0.000 description 1
- TXANJRRNRHLIGN-QPLCGJKRSA-N methyl (3z)-3-[[4-[[2-(methanesulfonamido)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)CCNS(C)(=O)=O)C=C1 TXANJRRNRHLIGN-QPLCGJKRSA-N 0.000 description 1
- WZOBASBNPSNEQM-IZHYLOQSSA-N methyl (3z)-3-[[4-[[2-(methylamino)-2-oxoethyl]-methylsulfonylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(CC(=O)NC)S(C)(=O)=O)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O WZOBASBNPSNEQM-IZHYLOQSSA-N 0.000 description 1
- USVLUTIAGKLFLC-RQZHXJHFSA-N methyl (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)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CN(C)CC(N)=O)C=C1 USVLUTIAGKLFLC-RQZHXJHFSA-N 0.000 description 1
- 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 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
- RZNYISXKOSUPRU-DQSJHHFOSA-N methyl (3z)-3-[[4-[[2-[bis(2-hydroxyethyl)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)\NC1=CC=C(N(C)C(=O)CN(CCO)CCO)C=C1 RZNYISXKOSUPRU-DQSJHHFOSA-N 0.000 description 1
- XTHMDGVWHHKQOE-RQZHXJHFSA-N methyl (3z)-3-[[4-[[2-[ethyl(methyl)amino]acetyl]-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(C)C(=O)CN(C)CC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O XTHMDGVWHHKQOE-RQZHXJHFSA-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
- 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 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
- QFVUURLADURDAG-IZHYLOQSSA-N methyl (3z)-3-[[4-[[2-hydroxyethyl(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)CCO)C=C1 QFVUURLADURDAG-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
- ZIQVXRACBDCYSE-RQZHXJHFSA-N methyl (3z)-3-[[4-[[3-(methanesulfonamido)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)CCCNS(C)(=O)=O)C=C1 ZIQVXRACBDCYSE-RQZHXJHFSA-N 0.000 description 1
- 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 1
- 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 1
- YWPMQYDTEUFJMU-RQZHXJHFSA-N methyl (3z)-3-[[4-[[[2-(dimethylamino)-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(=O)N(C)C)C=C1 YWPMQYDTEUFJMU-RQZHXJHFSA-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
- VGFCLVZQGXFUBP-FLWNBWAVSA-N methyl (3z)-3-[[4-[[benzyl(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)CC1=CC=CC=C1 VGFCLVZQGXFUBP-FLWNBWAVSA-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
- 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 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
- 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 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
- YMPRIZDZHDMBLD-ZIADKAODSA-N methyl (3z)-3-[[4-[[hexyl(methyl)amino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(CN(C)CCCCCC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O YMPRIZDZHDMBLD-ZIADKAODSA-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
- QYCYSOZNPHIUAH-QPLCGJKRSA-N methyl (3z)-3-[[4-[[methyl(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=C1 QYCYSOZNPHIUAH-QPLCGJKRSA-N 0.000 description 1
- PJHMTIYWQHYUSZ-QPLCGJKRSA-N methyl (3z)-3-[[4-[[methyl-[2-(methylamino)-2-oxoethyl]amino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(CN(C)CC(=O)NC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O PJHMTIYWQHYUSZ-QPLCGJKRSA-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
- 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 1
- ULPIJZRWGPHDDO-IZHYLOQSSA-N methyl (3z)-3-[[4-[acetyl-(2-amino-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(N)=O)C(C)=O)C=C1 ULPIJZRWGPHDDO-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
- 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
- BAIGDZLJOJIQHO-RQZHXJHFSA-N methyl (3z)-3-[[4-[acetyl-[2-(dimethylamino)ethyl]amino]-3-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(N(CCN(C)C)C(C)=O)C(Br)=C1 BAIGDZLJOJIQHO-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
- YWJXLPDWRJEYFX-QNGOZBTKSA-N methyl (3z)-3-[[4-[acetyl-[3-(dimethylamino)propyl]amino]anilino]methylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C\NC1=CC=C(N(CCCN(C)C)C(C)=O)C=C1 YWJXLPDWRJEYFX-QNGOZBTKSA-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
- IZTXKRFGALXQFK-KTMFPKCZSA-N methyl (3z)-3-[[4-[benzenesulfonyl-[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)S(=O)(=O)C1=CC=CC=C1 IZTXKRFGALXQFK-KTMFPKCZSA-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
- KNAYESYOVINZLR-KNWKATPGSA-N methyl (3z)-3-[[4-[benzyl-(2-piperidin-1-ylacetyl)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)CN1CCCCC1)CC1=CC=CC=C1 KNAYESYOVINZLR-KNWKATPGSA-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
- WPJBJLRIRXEPOX-KARKAFJISA-N methyl (3z)-3-[[4-[benzyl-[3-(dimethylamino)propanoyl]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)CCN(C)C)CC1=CC=CC=C1 WPJBJLRIRXEPOX-KARKAFJISA-N 0.000 description 1
- OHPWMIULDLOTAZ-MVJHLKBCSA-N methyl (3z)-3-[[4-[benzylsulfonyl-[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)S(=O)(=O)CC1=CC=CC=C1 OHPWMIULDLOTAZ-MVJHLKBCSA-N 0.000 description 1
- HMFSWIFHLWBBMS-ZIADKAODSA-N methyl (3z)-3-[[4-[butanoyl-[2-(dimethylamino)ethyl]amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(CCN(C)C)C(=O)CCC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O HMFSWIFHLWBBMS-ZIADKAODSA-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
- AAEHNSZVCCLBDC-ZIADKAODSA-N methyl (3z)-3-[[4-[butylsulfonyl-[2-(dimethylamino)ethyl]amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(CCN(C)C)S(=O)(=O)CCCC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O AAEHNSZVCCLBDC-ZIADKAODSA-N 0.000 description 1
- 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 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
- UFVYHADLRPSKQD-ZIADKAODSA-N methyl (3z)-3-[[4-[methyl(3-piperazin-1-ylpropanoyl)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)CCN1CCNCC1 UFVYHADLRPSKQD-ZIADKAODSA-N 0.000 description 1
- GYWGUXFFONDEKI-FLWNBWAVSA-N methyl (3z)-3-[[4-[methyl(3-piperidin-1-ylpropanoyl)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 GYWGUXFFONDEKI-FLWNBWAVSA-N 0.000 description 1
- NGUSBLZPSDYGSS-FCQUAONHSA-N methyl (3z)-3-[[4-[methyl(methylcarbamoyl)amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(C)C(=O)NC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O NGUSBLZPSDYGSS-FCQUAONHSA-N 0.000 description 1
- 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 1
- KWJGHMSJUKPZLM-DQSJHHFOSA-N methyl (3z)-3-[[4-[methyl-(2-morpholin-4-ylacetyl)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)CN1CCOCC1 KWJGHMSJUKPZLM-DQSJHHFOSA-N 0.000 description 1
- ZDVTYZZJKKLFIY-ZIADKAODSA-N methyl (3z)-3-[[4-[methyl-(2-piperidin-1-ylacetyl)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)CN1CCCCC1 ZDVTYZZJKKLFIY-ZIADKAODSA-N 0.000 description 1
- LGSYSPALXTUAJL-DQSJHHFOSA-N methyl (3z)-3-[[4-[methyl-(2-pyrrolidin-1-ylacetyl)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)CN1CCCC1 LGSYSPALXTUAJL-DQSJHHFOSA-N 0.000 description 1
- 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 1
- CISOKRFARQTZTP-DQSJHHFOSA-N methyl (3z)-3-[[4-[methylsulfonyl(2-piperazin-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(S(C)(=O)=O)CCN1CCNCC1 CISOKRFARQTZTP-DQSJHHFOSA-N 0.000 description 1
- VPJPIDGNIJXAFS-ZIADKAODSA-N methyl (3z)-3-[[4-[methylsulfonyl(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(S(C)(=O)=O)CCN1CCCCC1 VPJPIDGNIJXAFS-ZIADKAODSA-N 0.000 description 1
- LPFSELPFSKESFN-DQSJHHFOSA-N methyl (3z)-3-[[4-[methylsulfonyl(2-pyrrolidin-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(S(C)(=O)=O)CCN1CCCC1 LPFSELPFSKESFN-DQSJHHFOSA-N 0.000 description 1
- GAPKEPIGKOPJOC-DQSJHHFOSA-N methyl (3z)-3-[[4-[methylsulfonyl-(2-morpholin-4-yl-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)\NC(C=C1)=CC=C1N(S(C)(=O)=O)CC(=O)N1CCOCC1 GAPKEPIGKOPJOC-DQSJHHFOSA-N 0.000 description 1
- ZXKWSCZDPDUGNK-DQSJHHFOSA-N methyl (3z)-3-[[4-[methylsulfonyl-(2-oxo-2-piperazin-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(S(C)(=O)=O)CC(=O)N1CCNCC1 ZXKWSCZDPDUGNK-DQSJHHFOSA-N 0.000 description 1
- PMAGMLWLGFJATJ-ZIADKAODSA-N methyl (3z)-3-[[4-[methylsulfonyl-(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(S(C)(=O)=O)CC(=O)N1CCCCC1 PMAGMLWLGFJATJ-ZIADKAODSA-N 0.000 description 1
- CFSALSHJYOGOLL-DQSJHHFOSA-N methyl (3z)-3-[[4-[methylsulfonyl-(2-oxo-2-pyrrolidin-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(S(C)(=O)=O)CC(=O)N1CCCC1 CFSALSHJYOGOLL-DQSJHHFOSA-N 0.000 description 1
- ZHKJEDPUXSVIFH-IZHYLOQSSA-N methyl (3z)-3-[[4-[methylsulfonyl-[3-[(2,2,2-trifluoroacetyl)amino]propyl]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(CCCNC(=O)C(F)(F)F)S(C)(=O)=O)C=C1 ZHKJEDPUXSVIFH-IZHYLOQSSA-N 0.000 description 1
- VXYDONSUAPNUAL-MRCUWXFGSA-N methyl (3z)-3-[[methyl(piperidin-4-yl)amino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\N(C)C1CCNCC1 VXYDONSUAPNUAL-MRCUWXFGSA-N 0.000 description 1
- IAELOHNWFVWCNO-UHFFFAOYSA-N methyl 1-acetyl-3-[methoxy(phenyl)methylidene]-2-oxoindole-6-carboxylate Chemical compound O=C1N(C(C)=O)C2=CC(C(=O)OC)=CC=C2C1=C(OC)C1=CC=CC=C1 IAELOHNWFVWCNO-UHFFFAOYSA-N 0.000 description 1
- SHWVZUGUOIRBTR-UHFFFAOYSA-N methyl 2-hydroxy-3-[N-[4-[(2-oxopyrrolidin-1-yl)methyl]phenyl]-C-phenylcarbonimidoyl]-1H-indole-6-carboxylate Chemical compound COC(=O)C1=CC2=C(C=C1)C(=C(N2)O)C(=NC3=CC=C(C=C3)CN4CCCC4=O)C5=CC=CC=C5 SHWVZUGUOIRBTR-UHFFFAOYSA-N 0.000 description 1
- FPUPGTDVGVCPMU-DCXSSQDFSA-N methyl 3-amino-3-[4-[[(z)-(6-carbamoyl-2-oxo-1h-indol-3-ylidene)-phenylmethyl]amino]phenyl]propanoate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(C(N)CC(=O)OC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(N)=O)C=C2NC\1=O FPUPGTDVGVCPMU-DCXSSQDFSA-N 0.000 description 1
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Definitions
- the present invention relates to a new use of indolinones of general formula substituted in the 6 position, the tautomers, the diastereomers, the enantiomers, the mixtures thereof and the salts thereof, particularly the physiologically acceptable salts thereof.
- Remodeling is a normal response to tissue injury and inflammation that is observed in many tissues throughout the body. After resolution of the inflammation and repair of tissue damage, the tissue is generally returned to its original condition. Excessive uncontrolled tissue repair or the failure to stop remodeling when it is no longer required leads to condition known as fibrosis. Fibrosis is characterized by excessive deposition of extracellular matrix components and overgrowth of fibroblasts.
- Fibrosis can occur in all tissues but is especially prevalent in organs with frequent exposure to chemical and biological insults including the lung, skin, digestive tract, kidney, and liver (Eddy, 1996, J Am Soc Nephrol, 7(12):2495-503; Dacic et al., 2003, Am J Respir Cell Mol Biol, 29S: S5-9; Wynn, 2004, Nat Rev Immunol, 4(8):583-94). Fibrosis often severely compromises the normal function(s) of the organ and many fibrotic diseases are, in fact, life-threatening or severely disfiguring, such as idiopathic pulmonary fibrosis (IPF), liver cirrhosis, scleroderma, or renal fibrosis. Treatment options for these diseases are often limited to organ transplantation, a risky and expensive procedure.
- IPF idiopathic pulmonary fibrosis
- PDGF platelet-derived growth factor
- FGF fibroblast growth factor
- VEGF vascular endothelial growth factor
- EGF epidermal growth factor
- TGFb transforming growth factor beta growth factor families in the induction or persistence of fibrosis
- PDGF, EGF and FGF family members are potent mitogens for mesenchymal cells such as smooth muscle cells, myofibroblasts and fibroblasts (Benito et al., 1993, Growth Regul 3(3):172-9; Simm et al, 1998, Basic Res Cardiol, 93(S3):40-3; Klagsburn, Prog Growth Factor Res, 1989, 1(4):207-35; Kirkland et al., 1998, J Am Soc Nephrol, 9(8):1464-73), the very cells which supplant normal tissue in fibrosis and are believed to play a role in tissue remodeling (Abboud, 1995, Annu Rev Physiol., 57:297-309; Jinnin et al., 2004, J Cell Physiol, online; Martinet et al., 1996, Arch Toxicol 18:127-39; Desmouliere, Cell Biology International, 1995, 19:471-6; Jelaska et al., Springer Semin Immunopathol,
- FGF1/FGF2-deficient mice show dramatically decreased liver fibrosis after chronic carbon tetrachloride (CCl4) exposure (Yu et al., 2003, Am J Pathol, 163(4):1653-62).
- FGF expression is increased in human renal interstitial fibrosis where it strongly correlates with interstitial scarring (Strutz et al., 2000, Kidney Intl, 57:1521-38) as well as in a model of experimental lung fibrosis (Barrios et al., 1997, Am J Physiol, 273 (2 Pt 1):L451-8), again lending credence to the idea that fibrosis in various tissues has a common basis.
- VEGF vascular endothelial growth factor
- TGFb stimulates production of extracellular matrix proteins including fibronectin and collagens and is believed to play an important role in fibrosis in many tissues (Leask et al., 2004, FASEB J 18(7):816-27; Bartram et al., 2004, Chest 125(2):754-65; Strutz et al., 2003, Springer Semin Immunopathol, 24:459-76; Wynn, 2004, Nat Rev Immunol, 4(8):583-94). Inhibitors of TGFb production and signaling pathways are active in a number of fibrosis animal models (Wang et al., 2002, Exp Lung Res, 28:405-17; Laping, 2003, Curr Opin Pharmacol, 3(2):204-8).
- the present invention thus relates to the use of the compounds of above general formula I for the preparation of a medicament for the treatment or prevention of specific fibrotic diseases.
- the present invention also relates to a method for the treatment or prevention of specific fibrotic diseases, by administration to a patient in need thereof of a pharmaceutical composition comprising a compound of above general formula I, together with a pharmaceutically suitable carrier.
- a pharmaceutical composition comprising a compound of above general formula I, together with a pharmaceutically suitable carrier.
- patient is meant to comprise the mammalian animal body, preferably the human body.
- the present invention further relates to a pharmaceutical composition for the treatment or prevention of specific fibrotic diseases which comprises a compound of above general formula I alone or in combination with one or more further therapeutic agents.
- the compounds of above general formula I are the compounds in which
- X denotes an oxygen or sulphur atom
- R 1 denotes a hydrogen atom or a prodrug group such as a C 1-4 -alkoxycarbonyl or C 2-4 -alkanoyl group,
- R 2 denotes a carboxy group, a straight-chain or branched C 1-6 -alkoxy-carbonyl group, a C 4-7 -cycloalkoxy-carbonyl or an aryloxycarbonyl group,
- C 1-6 -alkoxy-carbonyl group which is terminally substituted in the alkyl moiety by a phenyl, heteroaryl, carboxy, C 1-3 -alkoxy-carbonyl, aminocarbonyl, C 1-3 -alkylamino-carbonyl or di-(C 1-3 -alkyl)-aminocarbonyl group,
- an aminocarbonyl or methylaminocarbonyl group an ethylaminocarbonyl group optionally substituted in the 2 position of the ethyl group by a hydroxy or C 1-3 -alkoxy group or a di-(C 1-2 -alkyl)-aminocarbonyl group,
- R 3 denotes a hydrogen atom, a C 1-6 -alkyl, C 3-7 -cycloalkyl, trifluoromethyl or heteroaryl group,
- a phenyl or naphthyl group a phenyl or naphthyl group mono- or disubstituted by a fluorine, chlorine, bromine or iodine atom, by a trifluoromethyl, C 1-3 -alkyl or C 2-3 -alkoxy group, whilst in the event of disubstitution the substituents may be identical or different and wherein the abovementioned unsubstituted as well as the mono- and disubstituted phenyl and naphthyl groups may additionally be substituted
- C 1-3 -alkylcarbonylamino N—(C 1-3 -alkyl)-C 1-3 -alkyl-carbonylamino, C 1-3 -alkylcarbonylamino-C 1-3 -alkyl, N—(C 1-3 -alkyl)-C 1-3 -alkylcarbonylamino-C 1-3 -alkyl, C 1-3 -alkyl-sulphonylamino, C 1-3 -alkylsulphonylamino-C 1-3 -alkyl, N—(C 1-3 -alkyl)-C 1-3 -alkylsulphonylamino-C 1-3 -alkyl or aryl-C 1-3 -alkylsulphonylamino group,
- R 4 denotes a C 3-7 -cycloalkyl group
- methylene group in the 4 position of a 6- or 7-membered cycloalkyl group may be substituted by an amino, C 1-3 -alkylamino or di-(C 1-3 -alkyl)-amino group or replaced by an —NH or —N(C 1-3 -alkyl) group,
- R 6 a phenyl group substituted by the group R 6 , which may additionally be mono- or disubstituted by fluorine, chlorine, bromine or iodine atoms, by C 1-5 -alkyl, trifluoromethyl, hydroxy, C 1-3 -alkoxy, carboxy, C 1-3 -alkoxycarbonyl, amino, acetylamino, C 1-3 -alkyl-sulphonylamino, aminocarbonyl, C 1-3 -alkyl-aminocarbonyl, di-(C 1-3 -alkyl)-aminocarbonyl, aminosulphonyl, C 1-3 -alkyl-aminosulphonyl, di-(C 1-3 -alkyl)-aminosulphonyl, nitro or cyano groups, wherein the substituents may be identical or different and wherein
- R 6 denotes a hydrogen, fluorine, chlorine, bromine or iodine atom
- a C 1-3 -alkoxy group a C 1-3 -alkoxy-C 1-3 -alkoxy, phenyl-C 1-3 -alkoxy, amino-C 2-3 -alkoxy, C 1-3 -alkylamino-C 2-3 -alkoxy, di-(C 1-3 -alkyl)-amino-C 2-3 -alkoxy, phenyl-C 1-3 -alkylamino-C 2-3 -alkoxy, N—(C 1-3 -alkyl) -phenyl-C 1-3 -alkylamino-C 2-3 -alkoxy, C 5-7 -cycloalkyleneimino-C 2-3 -alkoxy or C 1-3 -alkylmercapto group,
- methylene group in the 4 position of the 6- or 7-membered cycloalkyl moiety may be substituted by an amino, C 1-3 -alkylamino or di-(C 1-3 -alkyl)-amino group or replaced by an —NH or —N(C 1-3 -alkyl) group,
- a methylene group linked to the imino group may be replaced by a carbonyl or sulphonyl group or
- the cycloalkylene moiety may be fused to a phenyl ring or one or two hydrogen atoms may each be replaced by a C 1-3 -alkyl group and/or
- the methylene group in the 4 position of a 6- or 7-membered cycloalkyleneimino group may be substituted by a carboxy, C 1-3 -alkoxycarbonyl, aminocarbonyl, C 1-3 -alkylaminocarbonyl, di-(C 1-3 -alkyl)-aminocarbonyl, phenyl-C 1-3 -alkylamino or N—(C 1-3 -alkyl)-phenyl-C 1-3 -alkylamino group or
- R 7 denotes a C 3-7 -cycloalkyl group
- a —(CH 2 ) 2 group may be replaced by a —CO—NH group
- a —(CH 2 ) 3 group may be replaced by a —NH—CO—NH or —CO—NH—CO group or a —(CH 2 ) 4 group may be replaced by a —NH—CO—NH—CO group
- a hydrogen atom bound to a nitrogen atom may be replaced by a C 1-3 -alkyl group
- a hydroxy or C 1-3 -alkoxy group an amino, C 1-7 -alkylamino, di-(C 1-7 -alkyl) -amino, phenylamino, N-phenyl-C 1-3 -alkyl-amino, phenyl-C 1-3 -alkylamino, N—(C 1-3 -alkyl)-phenyl-C 1-3 -alkylamino or di-(phenyl-C 1-3 -alkyl)-amino group,
- guanidino group wherein one or two hydrogen atoms may each be replaced by a C 1-3 -alkyl group
- R 8 denotes a hydrogen atom or a C 1-3 -alkyl group
- n denotes one of the numbers 0, 1, 2 or 3 and
- R 9 denotes an amino, C 1-4 -alkylamino, di-(C 1-4 -alkyl)-amino, phenylamino, N—(C 1-4 -alkyl)-phenylamino, benzylamino,
- R 10 denotes a hydrogen atom, a C 1-3 -alkyl group, a C 1-3 -alkylcarbonyl, arylcarbonyl, phenyl-C 2-3 -alkyl-carbonyl, C 1-3 -alkylsulphonyl, arylsulphonyl or phenyl-C 1-3 -alkylsulphonyl group,
- n denotes one of the numbers 1, 2, 3 or 4,
- ⁇ denotes the number 1 or, if m denotes one of the numbers 2, 3 or 4, o may also denote the number 0 and
- R 11 denotes an amino, C 1-4 -alkylamino, di-(C 1-4 -alkyl)-amino, phenylamino, N—(C 1-4 -alkyl)-phenylamino, benzylamino, N—(C 1-4 -alkyl)-benzylamino, C 1-4 -alkoxy or C 1-3 -alkoxy-C 1-3 -alkoxy group, a di-(C 1-4 -alkyl)-amino-C 1-3 -alkylamino group optionally substituted in the 1 position by a C 1-3 -alkyl group or a 4- to 7-membered cycloalkyleneimino group, wherein the cycloalkylene moiety may be fused to a phenyl ring or in each case the methylene group in the 4 position of a 6- or 7-membered cycloalkyleneimino group may be replaced by an oxygen or sulph
- the cycloalkylene moiety may be fused to a phenyl group or to an oxazolo, imidazolo, thiazolo, pyridino, pyrazino or pyrimidino group optionally substituted by a fluorine, chlorine, bromine or iodine atom, by a nitro, C 1-3 -alkyl, C 1-3 -alkoxy or amino group, and/or
- one or two hydrogen atoms may each be replaced by a C 1-3 -alkyl, C 5-7 -cycloalkyl or phenyl group and/or
- the methylene group in the 3 position of a 5-membered cycloalkyleneimino group may be substituted by a hydroxy, hydroxy-C 1-3 -alkyl, C 1-3 -alkoxy or C 1-3 -alkoxy-C 1-3 -alkyl group,
- the methylene group in the 3 or 4 position of a 6- or 7-membered cycloalkyleneimino group may in each case be substituted by a hydroxy, hydroxy-C 1-3 -alkyl, C 1-3 -alkoxy, C 1-3 -alkoxy-C 1-3 -alkyl, carboxy, C 1-4 -alkoxycarbonyl, aminocarbonyl, C 1-3 -alkylaminocarbonyl, di-(C 1-3 -alkyl)-aminocarbonyl, phenyl-C 2-3 -alkylamino or N—(C 1-3 -alkyl)-phenyl-C 1-3 -alkyl-amino group or
- sulphinyl, sulphonyl may be replaced by an oxygen or sulphur atom, by a sulphinyl, sulphonyl, —NH, —N(C 1-3 -alkyl-), —N(phenyl), —N(phenyl-C 1-3 -alkyl-), —N(C 1-3 -alkyl-carbonyl-), —N(C 1-4 -alkyl-hydroxy-carbonyl-), —N(C 1-4 -alkoxy-carbonyl-), —N(benzoyl-) or —N(phenyl-C 1-3 -alkyl-carbonyl-) group,
- a methylene group linked to an imino-nitrogen atom of the cycloalkyleneimino group may be replaced by a carbonyl or sulphonyl group or in a 5- to 7-membered monocyclic cycloalkyleneimino group or a cycloalkyleneimino group fused to a phenyl group the two methylene groups linked to the imino-nitrogen atom may each be replaced by a carbonyl group,
- R 6 denotes a C 1-4 -alkyl group which is substituted by a carboxy, C 1-3 -alkoxycarbonyl, aminocarbonyl, C 1-3 -alkylaminocarbonyl or di-(C 1-3 -alkyl)-aminocarbonyl group or by a 4- to 7-membered cycloalkyleneiminocarbonyl group,
- R 12 denotes a hydrogen atom, a C 1-6 -alkyl or C 3-7 -cycloalkyl group or a C 1-3 -alkyl group terminally substituted by a phenyl, heteroaryl, trifluoromethyl, hydroxy, C 1-3 -alkoxy, aminocarbonyl, C 1-4 -alkylamino-carbonyl, di-(C 1-4 -alkyl)-amino-carbonyl, C 1-3 -alkyl-carbonyl, C 1-3 -alkyl-sulphonylamino, N—(C 1-3 -alkyl)-C 1-3 -alkyl-sulphonylamino, C 1-3 -alkyl-aminosulphonyl or di-(C 1-3 -alkyl) -aminosulphonyl group and
- p denotes one of the numbers 0, 1, 2 or 3 and
- R 13 assumes the meanings of the abovementioned group R 7 , or, if p denotes one of the numbers 1, 2 or 3, it may also denote a hydrogen atom,
- R 14 denotes a hydrogen atom, a C 1-4 -alkyl group, a C 1-3 -alkylcarbonyl, arylcarbonyl, phenyl-C 1-3 -alkylcarbonyl, heteroarylcarbonyl, heteroaryl-C 1-3 -alkylcarbonyl, C 1-4 -alkylsulphonyl, arylsulphonyl, phenyl-C 1-3 -alkylsulphonyl, heteroarylsulphonyl or heteroaryl-C 1-3 -alkyl-sulphonyl group,
- q denotes one of the numbers 1, 2, 3 or 4,
- r denotes the number 1 or, if q is one of the numbers 2, 3 or 4, it may also denote the number 0 and
- R 15 assumes the meanings of the abovementioned group R 7 .
- R 16 denotes a hydrogen atom or a C 1-4 -alkyl group optionally terminally substituted by a cyano, trifluoromethyl-carbonylamino or N—(C 1-3 -alkyl)-trifluoromethyl-carbonyl-amino group and
- R 17 denotes a C 1-3 -alkyl group
- all the single-bonded or fused phenyl groups contained in the groups mentioned under R 6 may be mono- or disubstituted by fluorine, chlorine, bromine or iodine atoms, by C 1-5 -alkyl, trifluoromethyl, hydroxy, C 1-3 -alkoxy, carboxy, C 1-3 -alkoxycarbonyl, aminocarbonyl, C 1-4 -alkylamino-carbonyl, di-(C 1-4 -alkyl)-amino-carbonyl, aminosulphonyl, C 1-3 -alkyl-aminosulphonyl, di-(C 1-3 -alkyl)-aminosulphonyl, C 1-3 -alkyl-sulphonylamino, nitro or cyano groups, wherein the substituents may be identical or different, or two adjacent hydrogen atoms of the phenyl groups may be replaced by a methylenedioxy group, and
- R 5 denotes a hydrogen atom or a C 1-3 -alkyl group
- an aryl group is meant a phenyl or naphthyl group optionally mono- or disubstituted by a fluorine, chlorine, bromine or iodine atom, by a cyano, trifluoromethyl, nitro, carboxy, aminocarbonyl, C 1-3 -alkyl or C 1-3 -alkoxy group and
- heteroaryl group a monocyclic 5- or 6-membered heteroaryl group optionally substituted by a C 1-3 -alkyl group in the carbon skeleton, wherein
- the 6-membered heteroaryl group contains one, two or three nitrogen atoms and
- the 5-membered heteroaryl group contains an imino group optionally substituted by a C 1-3 -alkyl or phenyl-C 1-3 -alkyl group, an oxygen or sulphur atom or
- an imino group optionally substituted by a C 1-3 -alkyl or phenyl-C 1-3 -alkyl group or an oxygen or sulphur atom and additionally a nitrogen atom or
- a phenyl ring may be fused to the abovementioned monocyclic heterocyclic groups via two adjacent carbon atoms and the bonding takes place via a nitrogen atom or via a carbon atom of the heterocyclic moiety or a fused phenyl ring,
- the saturated alkyl and alkoxy moieties with more than 2 carbon atoms which are present in the groups defined hereinbefore also include the branched isomers thereof, such as for example the isopropyl, tert.butyl, isobutyl group, unless otherwise stated, and
- the hydrogen atom of any carboxy group present or a hydrogen atom bound to a nitrogen atom may each be replaced by a group which can be cleaved in vivo.
- a group which can be cleaved in vivo from an imino or amino group is meant, for example, a hydroxy group, an acyl group such as the benzoyl or pyridinoyl group or a C 1-16 -alkanoyl group such as the formyl, acetyl, propionyl, butanoyl, pentanoyl or hexanoyl group, an allyloxycarbonyl group, a C 1-16 -alkoxycarbonyl group such as the methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, tert.butoxycarbonyl, pentoxycarbonyl, hexyloxycarbonyl, octyloxycarbonyl, nonyloxycarbonyl, decyloxycarbonyl, undecyloxycarbonyl, dodecyloxycarbonyl or hexadecyl
- R 6 denotes a C 1-8 -alkyl, C 5-7 -cycloalkyl, phenyl or phenyl-C 1-3 -alkyl group,
- R f denotes a hydrogen atom, a C 1-3 -alkyl, C 5-7 -cycloalkyl or phenyl group and
- R g denotes a hydrogen atom, a C 1-3 -alkyl or R e CO—O—(R f CR g )—O group wherein R e to R g are as hereinbefore defined,
- amino group may be a phthalimido group
- ester groups may also be used as a group which can be converted in vivo into a carboxy group
- R 2 denotes a straight-chain or branched C 1-6 -alkoxy-carbonyl group, a C 4-7 -cycloalkoxycarbonyl or a aryloxycarbonyl group,
- C 1-6 -alkoxy-carbonyl group which is terminally substituted in the alkyl moiety by a phenyl, heteroaryl, carboxy, C 1-3 -alkoxycarbonyl, aminocarbonyl, C 1-3 -alkylaminocarbonyl or di-(C 1-3 -alkyl)-aminocarbonyl group,
- R 2 denotes an aminocarbonyl or methylaminocarbonyl group, an ethylaminocarbonyl group optionally substituted in the 2 position of the ethyl group by a hydroxy or C 1-3 -alkoxy group or a di-(C 1-2 -alkyl)-aminocarbonyl group,
- R 4 denotes an R 7 -(C 1-4 -alkyl)-phenyl group, wherein
- R 7 denotes an amino, C 1-7 -alkylamino, di-(C 1-7 -alkyl)-amino, phenylamino, N-phenyl-C 2-3 -alkyl-amino, phenyl-C 1-3 -alkylamino, N—(C 1-3 -alkyl)-phenyl-C 1-3 -alkylamino or di-(phenyl-C 1-3 -alkyl)-amino group,
- Preferred compounds of general formula I are those wherein
- R 1 and R 3 are as hereinbefore defined and X denotes an oxygen atom
- R 2 denotes a carboxy group, a straight-chain or branched C 1-6 -alkoxy-carbonyl group, a C 5-7 -cycloalkoxycarbonyl or a phenoxycarbonyl group,
- C 1-3 -alkoxy-carbonyl group which is terminally substituted in the alkyl moiety by a phenyl, heteroaryl, carboxy, C 1-3 -alkoxycarbonyl, aminocarbonyl, C 1-3 -alkylaminocarbonyl or di-(C 1-3 -alkyl)-aminocarbonyl group,
- an aminocarbonyl or methylaminocarbonyl group an ethylaminocarbonyl group optionally substituted in the 2 position of the ethyl group by a hydroxy or C 1-3 -alkoxy group or a di-(C 1-2 -alkyl)-aminocarbonyl group,
- R 4 denotes a C 3-7 -cycloalkyl group
- methylene group in the 4 position of a 6- or 7-membered cycloalkyl group may be substituted by an amino, C 1-3 -alkylamino or di-(C 1-3 -alkyl)-amino group or replaced by an —NH or —N(C 1-3 -alkyl) group,
- R 6 a phenyl group substituted by the group R 6 , which may additionally be mono- or disubstituted by fluorine, chlorine or bromine atoms, by C 1-3 -alkyl, trifluoromethyl, hydroxy, C 1-3 -alkoxy, carboxy, C 1-3 -alkoxycarbonyl, amino, acetylamino, aminocarbonyl, C 1-3 -alkyl-aminocarbonyl, di-(C 1-3 -alkyl)-aminocarbonyl, nitro or cyano groups, wherein the substituents may be identical or different and wherein
- R 6 denotes a hydrogen, fluorine, chlorine, bromine or iodine atom
- a C 1-3 -alkoxy group an amino-C 2-3 -alkoxy, C 1-3 -alkylamino-C 2-3 -alkoxy, di-(C 1-3 -alkyl)-amino-C 2-3 -alkoxy, phenyl-C 1-3 -alkylamino-C 2-3 -alkoxy, N—(C 1-3 -alkyl)-phenyl-C 1-3 -alkylamino-C 2-3 -alkoxy, pyrrolidino-C 2-3 -alkoxy, piperidino-C 2-3 -alkoxy or C 1-3 -alkylmercapto group,
- a methylene group linked to the imino group may be replaced by a carbonyl or sulphonyl group or
- one or two hydrogen atoms may each be replaced by a C 1-3 -alkyl group and/or
- the methylene group in the 4 position of a 6- or 7-membered cycloalkyleneimino group may be substituted by a carboxy, C 1-3 -alkoxycarbonyl, aminocarbonyl, C 1-3 -alkylaminocarbonyl, di-(C 1-3 -alkyl)-aminocarbonyl, phenyl-C 1-3 -alkylamino or N—(C 1-3 -alkyl) -phenyl-C 1-3 -alkylamino group or
- sulphinyl may be replaced by an oxygen or sulphur atom, by a sulphinyl, sulphonyl, —NH or —N(C 1-3 -alkyl) group,
- R 7 denotes a C 5-7 -cycloalkyl group
- methylene group in the 4 position of a 6- or 7-membered cycloalkyl group may be replaced by an —NH or —N(C 1-3 -alkyl) group or
- a —(CH 2 ) 2 group may be replaced by a —CO—NH group
- a —(CH 2 ) 3 group may be replaced by a —NH—CO—NH—
- a —(CH 2 ) 4 group may be replaced by a —NH—CO—NH—CO group
- a hydrogen atom bound to a nitrogen atom may be replaced by a C 1-3 -alkyl group
- a ⁇ -hydroxy-C 2-3 -alkyl-amino N—(C 1-3 -alkyl)- ⁇ -hydroxy-C 2,3 -alkyl-amino, di-( ⁇ -hydroxy-C 2-3 -alkyl)-amino, di- ⁇ -(C 2-3 -alkoxy)-C 2-3 -alkyl)-amino or N-(dioxolan-2-yl)-C 1-3 -alkyl-amino group, a C 1-3 -alkylcarbonylamino-C 2-3 -alkyl-amino or C 1-3 -alkylcarbonylamino-C 2-3 -alkyl-N—(C 1-3 -alkyl)-amino group,
- guanidino group wherein a hydrogen atom may be replaced by a C 1-3 -alkyl group
- R 8 denotes a hydrogen atom or a C 1-3 -alkyl group
- n denotes one of the numbers 0, 1, 2 or 3 and
- R 9 denotes an amino, C 1-3 -alkylamino, di-(C 1-3 -alkyl)-amino, phenylamino, benzylamino or C 1-4 -alkoxy group, a 5- to 7-membered cycloalkyleneimino group, wherein the methylene group in position 4 of the piperidino group may be replaced by an oxygen or sulphur atom, by an —NH, —N(C 1-3 -alkyl), —N(phenyl), —N(C 1-3 -alkyl-carbonyl) or —N(benzoyl) group, or, if n denotes one of the numbers 1, 2 or 3, it may also denote a hydrogen atom,
- R 10 denotes a hydrogen atom, a C 1-3 -alkyl group, a C 1-3 -alkylcarbonyl or C 1-3 -alkylsulphonyl group,
- n denotes one of the numbers 1, 2 or 3,
- ⁇ denotes the number 1 or, if m is one of the numbers 2 or 3, ⁇ may also denote the number 0 and
- R 11 denotes an amino, C 1-3 -alkylamino, di-(C 1-3 -alkyl)-amino, C 1-4 -alkoxy or C 1-3 -alkoxy-C 1-3 -alkoxy group or a 5- to 7-membered cycloalkyleneimino group, wherein the methylene group in position 4 of the piperidino group may be replaced by an oxygen or sulphur atom, by an —NH, —N(C 1-3 -alkyl), —N(phenyl), —N(C 1-3 -alkyl-carbonyl) or —N(benzoyl) group,
- cycloalkylene moiety may be fused to a phenyl group or
- one or two hydrogen atoms may each be replaced by a C 1-3 -alkyl group and/or
- the methylene group in position 3 of the pyrrolidino group may be substituted by a hydroxy or C 1-3 -alkoxy group
- the methylene group in the 4 position of a 6- or 7-membered cycloalkyleneimino group may be substituted by a hydroxy, hydroxy-C 1-3 -alkyl, C 1-3 -alkoxy, carboxy, C 1-3 -alkoxycarbonyl, aminocarbonyl, C 1-3 -alkylaminocarbonyl, di-(C 1-3 -alkyl)-aminocarbonyl, phenyl-C 1-3 -alkylamino or N—(C 1-3 -alkyl)-phenyl-C 1-3 -alkylamino group or
- sulphinyl, sulphonyl may be replaced by an oxygen or sulphur atom, by a sulphinyl, sulphonyl, —NH, —N(C 1-3 -alkyl), —N(phenyl), —N(phenyl-C 1-3 -alkyl), —N(C 1-3 -alkyl-carbonyl), —N(C 1-4 -alkoxy-carbonyl), —N(benzoyl) or —N(phenyl-C 1-3 -alkyl-carbonyl) group,
- a methylene group linked to an imino-nitrogen atom of the cycloalkyleneimino group may be replaced by a carbonyl or sulphonyl group or in a 5- to 6-membered monocyclic cycloalkyleneimino group or a cycloalkyleneimino group fused to a phenyl group the two methylene groups linked to the imino-nitrogen atom may each be replaced by a carbonyl group,
- R 6 denotes a C 1-4 -alkyl group which is terminally substituted by a carboxy, C 1-3 -alkoxycarbonyl, aminocarbonyl, C 1-3 -alkylaminocarbonyl or di-(C 1-3 -alkyl)-aminocarbonyl group or by a 4- to 7-membered cycloalkyleneiminocarbonyl group,
- R 12 denotes a hydrogen atom, a C 1-3 -alkyl, C 5-7 -cycloalkyl, phenyl-C 1-3 -alkyl or heteroaryl-C 1-3 -alkyl group and
- p denotes one of the numbers 0, 1, 2 or 3 and
- R 13 assumes the meanings of the abovementioned group R 7 , or, if p denotes one of the numbers 1, 2 or 3, it may also denote a hydrogen atom,
- R 14 denotes a hydrogen atom, a C 1-4 -alkyl group, a C 1-3 -alkylcarbonyl, phenylcarbonyl, phenyl-C 2-3 -alkylcarbonyl, heteroarylcarbonyl, heteroaryl-C 1-3 -alkylcarbonyl, C 1-4 -alkylsulphonyl, phenylsulphonyl, phenyl-C 1-3 -alkylsulphonyl-heteroarylsulphonyl or heteroaryl-C 1-3 -alkyl-sulphonyl group,
- q denotes one of the numbers 1, 2, 3 or 4,
- r denotes the number 1 or, if q is one of the numbers 2, 3 or 4, it may also denote the number 0 and
- R 15 assumes the meanings of the abovementioned group R 7 .
- R 16 denotes a hydrogen atom or a C 1-4 -alkyl group optionally terminally substituted by a cyano, trifluoromethyl-carbonylamino or N—(C 1-3 -alkyl)-trifluoromethyl-carbonyl-amino group and
- R 17 denotes a C 1-3 -alkyl group
- phenyl groups contained in the groups mentioned under R 6 may be mono- or disubstituted by fluorine, chlorine or bromine atoms, by C 1-3 -alkyl, trifluoromethyl, hydroxy, C 1-3 -alkoxy, carboxy, C 1-3 -alkoxycarbonyl, aminocarbonyl, C 1-3 -alkyl-aminocarbonyl, aminosulphonyl, C 1-3 -alkyl-aminosulphonyl, nitro or cyano groups, wherein the substituents may be identical or different, or two adjacent hydrogen atoms of the phenyl groups may be replaced by a methylenedioxy group, and
- R 5 denotes a hydrogen atom or a C 1-3 -alkyl group
- heteroaryl group as mentioned above is meant a pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyrrolyl, furyl, thienyl, oxazolyl, thiazolyl, pyrazolyl, imidazolyl or triazolyl group optionally substituted in the carbon skeleton by a C 1-3 -alkyl group wherein a hydrogen atom bound to a nitrogen atom may be replaced by a C 1-3 -alkyl or phenyl-C 1-3 -alkyl group and wherein the 5-membered heteroaryl groups containing at least one imino group are bound via a carbon or nitrogen atom,
- a hydrogen atom bound to a nitrogen atom in the abovementioned groups may be replaced by a group which can be cleaved in vivo, particularly by an acetyl or tert.butoxycarbonyl group,
- the carboxy groups contained in the abovementioned groups may each be substituted by a group which can be cleaved in vivo and may occur, for example, in the form of the tert.butoxycarbonyl group,
- saturated alkyl and alkoxy moieties contained in the abovementioned groups which contain more than 2 carbon atoms, may be straight-chain or branched, unless otherwise stated,
- R 2 denotes a straight-chain or branched Cl -alkoxy-carbonyl group, a C 3-7 -cycloalkoxycarbonyl or a phenoxycarbonyl group,
- C 1-3 -alkoxy-carbonyl group which is terminally substituted in the alkyl moiety by a phenyl-carboxy, C 1-3 -alkoxycarbonyl, aminocarbonyl, C 1-3 -alkylaminocarbonyl or di-(C 1-3 -alkyl)-aminocarbonyl group,
- a second sub-group of preferred compounds of general formula I deserving special mention comprises those wherein
- R 2 denotes an aminocarbonyl or methylaminocarbonyl group, an ethylaminocarbonyl group optionally substituted in the 2 position of the ethyl group by a hydroxy or C 1-3 -alkoxy group or a di-(C 1-2 -alkyl)-aminocarbonyl group,
- a third sub-group of preferred compounds of general formula I deserving special mention comprises those wherein
- R 4 denotes an R 7 -(n-C 1-4 -alkyl)-phenyl group, wherein
- R 7 denotes an amino, C 1-6 -alkylamino, di-(C 1-6 -alkyl)-amino, phenylamino, N-phenyl-C 2-3 -alkyl-amino, phenyl-C 1-3 -alkylamino, N—(C 1-3 -alkyl)-phenyl-C 1-3 -alkylamino or di-(phenyl-C 1-3 -alkyl)-amino group,
- X denotes an oxygen atom
- R 1 denotes a hydrogen atom
- R 2 denotes a carboxy group, a straight-chain or branched C 1-4 -alkoxycarbonyl group or a phenoxycarbonyl group,
- C 1-3 -alkoxy-carbonyl group which is terminally substituted in the alkyl moiety by a phenyl, carboxy, C 1-3 -alkoxycarbonyl, aminocarbonyl, C 1-3 -alkylaminocarbonyl or di-(C 1-3 -alkyl)-aminocarbonyl group,
- an aminocarbonyl or methylaminocarbonyl group an ethylaminocarbonyl group optionally substituted in the 2 position of the ethyl group by a hydroxy or C 1-3 -alkoxy group or a di-(C 1-2 -alkyl)-aminocarbonyl group,
- R 3 denotes a C 1-4 -alkyl group or a phenyl group which may be substituted by a fluorine, chlorine or bromine atom, by a trifluoromethyl, C 1-3 -alkyl, hydroxy or C 1-3 -alkoxy group,
- R 4 denotes a C 5-6 -cycloalkyl group
- methylene group in position 4 of the cyclohexyl group may be substituted by an amino, C 1-3 -alkylamino or di-(C 1-3 -alkyl)-amino group or replaced by an —NH or —N(C 1-3 -alkyl) group,
- a phenyl group a phenyl group disubstituted by C 1-3 -alkyl, C 1-3 -alkoxy or nitro groups, wherein the substituents may be identical or different, or
- R 6 a phenyl group substituted by the group R 6 , which may additionally be substituted by a fluorine, chlorine or bromine atom or by an amino or nitro group, wherein R 6 denotes a fluorine, chlorine or bromine atom,
- the methylene group in position 4 of the piperidino group may be replaced by an oxygen or sulphur atom, by an —NH or —N(C 1-3 -alkyl) group,
- R 7 denotes a C 5-7 -cycloalkyl group
- a —(CH 2 ) 2 group may be replaced by a —CO—NH group
- a —(CH 2 ) 3 group may be replaced by an —NH—CO—NH—
- a —(CH 2 ) 4 group may be replaced by an —NH—CO—NH—CO group
- a hydrogen atom bound to a nitrogen atom may be replaced by a C 1-3 -alkyl group
- a phenyl or pyridinyl group or a pyrrolyl pyrazolyl, imidazolyl or triazolyl group bound via a carbon or nitrogen atom
- the abovementioned heteroaromatic groups in the carbon skeleton may be substituted by a C 1-3 -alkyl group or a hydrogen atom bound to a nitrogen atom may be replaced by a C 1-3 -alkyl group
- guanidino group wherein a hydrogen atom may be replaced by a C 1-3 -alkyl group
- R 8 denotes a hydrogen atom or a C 1-3 -alkyl group
- n denotes one of the numbers 0, 1, 2 or 3 and
- R 9 denotes an amino, C 1-3 -alkylamino, di-(C 1-3 -alkyl)-amino or C 1-4 -alkoxy group, a 5- or 6-membered cycloalkyleneimino group, wherein the methylene group in position 4 of the piperidino group may be replaced by an —NH, —N(C 1-3 -alkyl) or —N(C 1-3 -alkyl-carbonyl) group, or, if n denotes one of the numbers 1, 2 or 3, R, may also denote a hydrogen atom,
- R 10 denotes a hydrogen atom or a C 1-3 -alkyl group
- n denotes one of the numbers 1, 2 or 3,
- ⁇ denotes the number 1 or, if m is one of the numbers 2 or 3, ⁇ may also denote the number 0 and R 11 denotes an amino, C 1-3 -alkylamino, di-(C 1-3 -alkyl)-amino, C 1-4 -alkoxy or methoxy-C 1-3 -alkoxy group or a 5- or 6-membered cycloalkyleneimino group, wherein the methylene group in position 4 of the piperidino group may be replaced by an —NH, —N(C 1-3 -alkyl) or —N(C 1-3 -alkyl-carbonyl) group,
- the methylene group in position 3 of the pyrrolidino group may be substituted by a hydroxy group
- the methylene group in position 4 of the piperidino group may be substituted by a hydroxy, hydroxy-C 1-3 -alkyl or C 1-3 -alkoxy group or
- sulphinyl, sulphonyl may be replaced by an oxygen or sulphur atom, by a sulphinyl, sulphonyl, —NH, —N(C 1-3 -alkyl), —N(C 1-3 -alkyl-carbonyl), —N(benzoyl) or —N(phenyl-C 1-3 -alkyl-carbonyl) group,
- a methylene group linked to an imino-nitrogen atom of the pyrrolidino, piperidino or piperazino group may be replaced by a carbonyl group
- R 6 denotes a straight-chain C 1-3 -alkyl group which is terminally substituted by a carboxy or C 1-3 -alkoxy-carbonyl group
- R 12 denotes a hydrogen atom, a C 1-3 -alkyl or phenyl-C 1-3 -alkyl group
- p denotes one of the numbers 0, 1 or 2 and
- R 13 denotes an amino, C 1-4 -alkylamino, di-(C 1-4 -alkyl)-amino, benzylamino, N—(C 1-3 -alkyl) -benzylamino, C 1-3 -alkoxy-C 1-3 -alkylamino, N—(C 1-3 -alkyl)-C 1-3 -alkoxy-C 1-3 -alkylamino, di-(2-methoxy-ethyl)-amino, di-( ⁇ -hydroxy-C 1-3 -alkyl)-amino or aminocarbonyl-methyl-N-(methyl)-amino group,
- R 14 denotes a hydrogen atom, a C 1-4 -alkyl, C 2-3 -alkyl-carbonyl, phenylcarbonyl, phenyl-C 1-3 -alkylcarbonyl, furyl-carbonyl, pyridinyl-carbonyl, furyl-C 1-3 -alkylcarbonyl, pyridinyl-C 1-3 -alkylcarbonyl, C 1-4 -alkylsulphonyl, phenylsulphonyl or phenyl-C 1-3 -alkylsulphonyl group,
- q denotes one of the numbers 1, 2 or 3,
- r denotes the number 1 or, if q is one of the numbers 2 or 3, it may also denote the number 0 and
- R 15 denotes an amino, C 1-4 -alkylamino, di-(C 1-4 -alkyl)-amino, phenylamino, N—(C 1-4 -alkyl)-phenylamino, benzylamino or N—(C 1-4 -alkyl) -benzylamino group,
- R 16 denotes a hydrogen atom or a C 1-3 -alkyl group optionally terminally substituted by a cyano, trifluoromethyl-carbonylamino or N—(C 1-3 -alkyl)-trifluoromethyl-carbonyl-amino group and
- R 17 denotes a C 1-3 -alkyl group
- R 5 denotes a hydrogen atom
- carboxy groups contained in the abovementioned groups may also be present in the form of the tert.butoxycarbonyl precursor group and
- saturated alkyl and alkoxy moieties contained in the abovementioned groups which contain more than 2 carbon atoms, may be straight-chain or branched, unless otherwise stated,
- R 2 denotes a straight-chain or branched C 1-4 -alkoxycarbonyl group or a phenoxycarbonyl group
- C 1-3 -alkoxycarbonyl group which is terminally substituted in the alkyl moiety by a phenyl-carboxy, C 1-3 -alkoxycarbonyl, aminocarbonyl, C 1-3 -alkylaminocarbonyl or di-(C 1-3 -alkyl)-aminocarbonyl group, or
- R 4 denotes an R 7 -(n-C 1-3 -alkyl)-phenyl group, wherein
- R 7 denotes an amino, C 1-6 -alkylamino, di-(C 1-4 -alkyl)-amino, ⁇ -hydroxy-C 2-3 -alkyl-amino,
- a second subgroup of particularly preferred compounds of general formula I deserving special mention comprises those wherein
- R 2 denotes an aminocarbonyl or methylaminocarbonyl group, an ethylaminocarbonyl group optionally substituted in the 2 position of the ethyl group by a hydroxy or C 1-3 -alkoxy group or a di-(C 1-2 -alkyl)-aminocarbonyl group and
- R 4 denotes a R 7 -(n-C 1-3 -alkyl)-phenyl group, wherein
- R 7 denotes an amino, C 1-6 -alkylamino, di-(C 1-4 -alkyl)-amino, ⁇ -hydroxy-C 2-3 -alkyl-amino, N—(C 1-3 -alkyl)- ⁇ -hydroxy-C 2-3 -alkyl-amino, di-( ⁇ -hydroxy-C 2-3 -alkyl)-amino or di-( ⁇ -(C 1-3 -alkoxy)-C 2-3 -alkyl)-amino group,
- X denotes an oxygen atom
- R 1 and R 5 each denote a hydrogen atom
- R 2 denotes a methoxycarbonyl, ethoxycarbonyl or aminocarbonyl group
- R 3 denotes a phenyl group
- R 4 denotes a phenyl group monosubstituted by the group R 6 , wherein
- R 6 denotes an N-methyl-imidazol-2-yl group
- R 12 denotes a C 1-3 -alkyl group
- p denotes one of the numbers 1 or 2 and
- R 13 denotes a di-(C 1-3 -alkyl)-amino group
- R 14 denotes a C 1-3 -alkyl-carbonyl or C 1-3 -alkylsulphonyl group
- q denotes one of the numbers 1, 2 or 3,
- r denotes the number 1 or, if q is one of the numbers 2 or 3, r may also denote the number 0 and
- R 15 denotes a di-(C 1-3 -alkyl)-amino group
- saturated alkyl moieties contained in the abovementioned groups which contain more than 2 carbon atoms may be straight-chain or branched, unless otherwise stated,
- R 2 denotes a methoxycarbonyl or ethoxycarbonyl group
- R 4 denotes a di-(C 1-3 -alkyl)-amino-C 1-3 -alkylphenyl group or
- Another subgroup of compounds of general formula I comprises those wherein
- X denotes an oxygen or sulphur atom
- R 1 denotes a hydrogen atom or a prodrug group such as a C 1-4 -alkoxycarbonyl or C 2-4 -alkanoyl group,
- R 2 denotes a carboxy group, a straight-chain or branched C 1-6 -alkoxycarbonyl group, a C 5-7 -cycloalkoxycarbonyl or phenyl-C 1-3 -alkoxycarbonyl group, an aminocarbonyl or C 1-2 -alkylaminocarbonyl group or, if R 4 does not denote an aminosulphonyl-phenyl or N—(C 1-5 -alkyl)-C 1-3 -alkylaminocarbonyl-phenyl group, a di-(C 1-2 -alkyl)-aminocarbonyl group,
- R 3 denotes a hydrogen atom, a C 1-6 -alkyl, C 3-7 -cycloalkyl, trifluoromethyl or heteroaryl group,
- a phenyl or naphthyl group a phenyl or naphthyl group mono- or disubstituted by a fluorine, chlorine, bromine or iodine atom, by a trifluoromethyl, C 1-3 -alkyl or C 1-3 -alkoxy group, whilst in the event of disubstitution the substituents may be identical or different and wherein the abovementioned unsubstituted as well as the mono- and disubstituted phenyl and naphthyl groups may additionally be substituted
- C 1-3 -alkylcarbonylamino N—(C 1-3 -alkyl)-C 1-3 -alkylcarbonylamino, C 1-3 -alkylcarbonylamino-C 1-3 -alkyl, N—(C 1-3 -alkyl)-C 1-3 -alkylcarbonylamino-C 1-3 -alkyl, C 1-3 -alkylsulphonylamino, C 1-3 -alkylsulphonylamino-C 1-3 -alkyl, N—(C 1-3 -alkyl)-C 1-3 -alkylsulphonylamino-C 1-3 -alkyl or aryl-C 1-3 -alkylsulphonylamino group,
- R 4 denotes a C 3-7 -cycloalkyl group
- methylene group in the 4 position of a 6- or 7-membered cycloalkyl group may be substituted by an amino, C 1-3 -alkylamino or di-(C 1-3 -alkyl)-amino group or replaced by an —NH or —N(C 1-3 -alkyl) group,
- R 6 a phenyl group substituted by the group R 6 , which may additionally be substituted by a fluorine, chlorine, bromine or iodine atom, by a C 1-5 alkyl, trifluoromethyl, C 1-3 -alkoxy, carboxy, C 1-3 -alkoxycarbonyl, aminosulphonyl, nitro or cyano group, wherein
- R 6 denotes a hydrogen, fluorine, chlorine, bromine or iodine atom
- a C 1-3 -alkoxy group optionally unsubstituted by 1 to 3 fluorine atoms, a C 1-3 -alkoxy-C 1-3 -alkoxy, phenyl-C 1-3 -alkoxy, amino-C 2-3 -alkoxy, C 1-3 -alkylamino-C 2-3 -alkoxy, di-(C 1-3 -alkyl)-amino-C 2-3 -alkoxy, phenyl-C 1-3 -alkylamino-C 2-3 -alkoxy, N—(C 1-3 -alkyl)-phenyl-C 1-3 -alkylamino-C 2-3 -alkoxy, C 5-7 -cycloalkyleneimino-C 2-3 -alkoxy or C 1-3 -alkylmercapto group,
- a methylene group linked to the imino group may be replaced by a carbonyl or sulphonyl group or
- cycloalkylene moiety may be fused to a phenyl ring or
- one or two hydrogen atoms may each be replaced by a C 1-3 -alkyl group and/or
- the methylene group in the 4 position of a 6- or 7-membered cycloalkyleneimino group may be substituted by a carboxy, C 1-3 -alkoxycarbonyl, aminocarbonyl, C 1-3 -alkylaminocarbonyl, di-(C 1-3 -alkyl) -aminocarbonyl, phenyl-C 1-3 -alkylamino or N—(C 1-3 -alkyl)-phenyl-C 1-3 -alkylamino group or
- sulphinyl may be replaced by an oxygen or sulphur atom, by a sulphinyl, sulphonyl, —NH, —N(C 1-3 -alkyl), —N(phenyl), —N(C 1-3 -alkyl-carbonyl) or —N(benzoyl) group,
- a methylene group linked to the imino group may be replaced by a carbonyl or sulphonyl group or
- the cycloalkylene moiety may be fused to a phenyl group or to an oxazolo, imidazolo, thiazolo, pyridino, pyrazino or pyrimidino group optionally substituted by a fluorine, chlorine, bromine or iodine atom, by a nitro, C 1-3 -alkyl, C 1-3 -alkoxy or amino group or
- one or two hydrogen atoms may each be replaced by a C 1-3 -alkyl, C 5-7 -cycloalkyl or phenyl group and/or
- the methylene group in the 4 position of a 6- or 7-membered cycloalkyleneimino group may be substituted by a hydroxy, carboxy, C 1-4 -alkoxycarbonyl, aminocarbonyl, C 1-3 -alkylaminocarbonyl, di-(C 1-3 -alkyl) -aminocarbonyl, phenyl-C 1-3 -alkylamino or N—(C 1-3 -alkyl)-phenyl-C 1-3 -alkylamino group or
- R 8 denotes a hydrogen atom or a C 1-3 -alkyl group
- n denotes one of the numbers 0, 1, 2 or 3 and
- R 9 denotes an amino, C 1-4 -alkylamino, phenylamino, N—(C 1-4 -alkyl)-phenylamino, benzylamino, N—(C 1-4 -alkyl)-benzylamino or di-(C 1-4 -alkyl)-amino group, a 4- to 7-membered cycloalkyleneimino group, whilst in each case the methylene group in the 4 position of a 6- or 7-membered cycloalkyleneimino group may be replaced by an oxygen or sulphur atom, by a sulphinyl,
- sulphonyl —NH, —N(C 1-3 -alkyl), —N(phenyl), —N(C 1-3 -alkyl-carbonyl) or —N(benzoyl) group, or, if n denotes one of the numbers 1, 2 or 3, it may also denote a hydrogen atom,
- R 10 denotes a hydrogen atom, a C 1-3 -alkyl group, a C 1-3 -alkylcarbonyl, arylcarbonyl, phenyl-C 1-3 -alkylcarbonyl, C 1-3 -alkylsulphonyl, arylsulphonyl or phenyl-C 1-3 -alkylsulphonyl group,
- n denotes one of the numbers 1, 2, 3 or 4,
- ⁇ denotes one of the numbers 0 or 1 and
- R 11 denotes an amino, C 1-4 -alkylamino, phenylamino, N—(C 1-4 -alkyl)-phenylamino, benzylamino, N—(C 1-4 -alkyl)-benzylamino or di-(C 1-4 -alkyl)-amino group, a 4- to 7-membered cycloalkyleneimino group, wherein the cycloalkylene moiety may be fused to a phenyl ring or in each case the methylene group in the 4 position of a 6- or 7-membered cycloalkyleneimino group may be replaced by an oxygen or sulphur atom, by a sulphinyl, sulphonyl, —NH, —N(C 1-3 -alkyl), —N(phenyl), —N(C 1-3 -alkyl-carbonyl) or —N(benzoyl) group, a C
- phenyl groups contained in the groups mentioned under R 6 may be mono- or disubstituted by fluorine, chlorine, bromine or iodine atoms, by C 1-5 -alkyl, trifluoromethyl, C 1-3 -alkoxy, carboxy, C 1-3 -alkoxycarbonyl, aminosulphonyl, nitro or cyano groups, wherein the substituents may be identical or different, or two adjacent hydrogen atoms of the phenyl groups may be replaced by a methylenedioxy group, and
- R 5 denotes a hydrogen atom or a C 1-3 -alkyl group
- aryl group a phenyl or naphthyl group optionally mono- or disubstituted by a fluorine, chlorine, bromine or iodine atom, by a trifluoromethyl, C 1-3 -alkyl or C 1-3 -alkoxy group and
- heteroaryl group a monocyclic 5- or 6-membered heteroaryl group optionally substituted by a C 1-3 -alkyl group, wherein the 6-membered heteroaryl group contains one, two or three nitrogen atoms and the 5-membered heteroaryl group contains an imino group optionally substituted by a C 1-3 -alkyl group, an oxygen or sulphur atom or an imino group optionally substituted by a C 1-3 -alkyl group and an oxygen or sulphur atom or one or two nitrogen atoms, and moreover a phenyl ring may be fused to the abovementioned monocyclic heterocyclic groups via two adjacent carbon atoms,
- the saturated alkyl and alkoxy moieties present in the groups defined above which contain more than 2 carbon atoms also include the branched isomers thereof such as, for example, the isopropyl, tert.butyl or isobutyl group, unless otherwise stated, and
- any carboxy, amino or imino group present may be substituted by a group which can be cleaved in viva,
- TBTU O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium-tetrafluoroborate
- the aqueous phase is three times extracted with ethyl acetate and the combined organic phases are dried over sodium sulphate. After evaporation of the solvent the residue is purified over a silica gel column with methylene chloride/methanol (9:1) as eluant.
- starting material VI 1-acetyl-3-(1-ethoxy-methylene)-6-methoxycarbonyl-2-indolinone (starting material VI) are dissoled in 150 ml of methanol and 86.4 ml of 1N sodium hydroxide solution are added. The mixture is refluxed for 8.5 hrs. After that time 86.4 ml of 1N hydrochloric acid are added. The residue is filtered off and dried at 90° C.
- Tautomers, stereoisomers or physiologically acceptable salts of these compounds are also contemplated within the scope of the present invention, and may be obtained using the methods described in WO 01/27081, the content of which is herein incorporated by reference.
- a particularly preferred compound is the monoethanesulphonate salt of 3-Z-[1-(4-(N-((4-methyl-piperazin-1-yl)-methylcarbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone, disclosed for example in WO 04/13099, the content of which is incorporated herein by reference.
- WO 04/13099 describes metabolites and prodrugs of the compound 3-Z-[1-(4-(N-((4-methyl-piperazin-1-yl)-methylcarbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone-monoethanesulphonate.
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US12/645,151 US20100204211A1 (en) | 2004-12-24 | 2009-12-22 | Medicaments for the treatment or prevention of fibrotic diseases |
US14/184,821 US20140296217A1 (en) | 2004-12-24 | 2014-02-20 | Medicaments for the treatment or prevention of fibrotic diseases |
US14/982,179 US10154990B2 (en) | 2004-12-24 | 2015-12-29 | Medicaments for the treatment or prevention of fibrotic diseases |
US16/167,567 US20190038600A1 (en) | 2004-12-24 | 2018-10-23 | Medicaments for the treatment or prevention of fibrotic deiseases |
US16/921,043 US20200330435A1 (en) | 2004-12-24 | 2020-07-06 | Medicaments for the treatment or prevention of fibrotic diseases |
US18/363,779 US20230372297A1 (en) | 2004-12-24 | 2023-08-02 | Medicaments for the treatment or prevention of fibrotic diseases |
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US12/645,151 Abandoned US20100204211A1 (en) | 2004-12-24 | 2009-12-22 | Medicaments for the treatment or prevention of fibrotic diseases |
US14/184,821 Abandoned US20140296217A1 (en) | 2004-12-24 | 2014-02-20 | Medicaments for the treatment or prevention of fibrotic diseases |
US14/982,179 Active 2026-01-08 US10154990B2 (en) | 2004-12-24 | 2015-12-29 | Medicaments for the treatment or prevention of fibrotic diseases |
US16/167,567 Abandoned US20190038600A1 (en) | 2004-12-24 | 2018-10-23 | Medicaments for the treatment or prevention of fibrotic deiseases |
US16/921,043 Abandoned US20200330435A1 (en) | 2004-12-24 | 2020-07-06 | Medicaments for the treatment or prevention of fibrotic diseases |
US18/363,779 Pending US20230372297A1 (en) | 2004-12-24 | 2023-08-02 | Medicaments for the treatment or prevention of fibrotic diseases |
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US12/645,151 Abandoned US20100204211A1 (en) | 2004-12-24 | 2009-12-22 | Medicaments for the treatment or prevention of fibrotic diseases |
US14/184,821 Abandoned US20140296217A1 (en) | 2004-12-24 | 2014-02-20 | Medicaments for the treatment or prevention of fibrotic diseases |
US14/982,179 Active 2026-01-08 US10154990B2 (en) | 2004-12-24 | 2015-12-29 | Medicaments for the treatment or prevention of fibrotic diseases |
US16/167,567 Abandoned US20190038600A1 (en) | 2004-12-24 | 2018-10-23 | Medicaments for the treatment or prevention of fibrotic deiseases |
US16/921,043 Abandoned US20200330435A1 (en) | 2004-12-24 | 2020-07-06 | Medicaments for the treatment or prevention of fibrotic diseases |
US18/363,779 Pending US20230372297A1 (en) | 2004-12-24 | 2023-08-02 | Medicaments for the treatment or prevention of fibrotic diseases |
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---|---|---|---|---|
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JP2023519600A (ja) | 2020-04-01 | 2023-05-11 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 線維性状態の治療におけるバイオマーカーの使用 |
WO2021204856A1 (en) | 2020-04-08 | 2021-10-14 | Mission Therapeutics Limited | N-cyanopyrrolidines with activity as usp30 inhibitors |
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Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6762180B1 (en) * | 1999-10-13 | 2004-07-13 | Boehringer Ingelheim Pharma Kg | Substituted indolines which inhibit receptor tyrosine kinases |
Family Cites Families (177)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4460581A (en) | 1982-10-12 | 1984-07-17 | Boehringer Ingelheim Kg | (1-Hydroxy-2-amino-alkyl)-substituted benzoxazinones and benzoxazolinones |
JPH06502178A (ja) | 1990-12-31 | 1994-03-10 | 藤沢薬品工業株式会社 | イミダゾトリアジン誘導体 |
GB9816837D0 (en) | 1998-08-04 | 1998-09-30 | Zeneca Ltd | Amide derivatives |
US5656644A (en) | 1994-07-20 | 1997-08-12 | Smithkline Beecham Corporation | Pyridyl imidazoles |
US5716972A (en) | 1993-01-13 | 1998-02-10 | Smithkline Beecham Corporation | Pyridyl substituted imidazoles |
IL104369A0 (en) | 1992-01-13 | 1993-05-13 | Smithkline Beecham Corp | Novel compounds and compositions |
GB9303993D0 (en) | 1993-02-26 | 1993-04-14 | Fujisawa Pharmaceutical Co | New heterocyclic derivatives |
US5670527A (en) | 1993-07-16 | 1997-09-23 | Smithkline Beecham Corporation | Pyridyl imidazole compounds and compositions |
US5593992A (en) | 1993-07-16 | 1997-01-14 | Smithkline Beecham Corporation | Compounds |
US5593991A (en) | 1993-07-16 | 1997-01-14 | Adams; Jerry L. | Imidazole compounds, use and process of making |
US5543520A (en) | 1993-10-01 | 1996-08-06 | Ciba-Geigy Corporation | Pyrimidine derivatives |
WO1995009851A1 (en) | 1993-10-01 | 1995-04-13 | Ciba-Geigy Ag | Pharmacologically active pyrimidineamine derivatives and processes for the preparation thereof |
DK0672041T3 (da) | 1993-10-01 | 2002-02-25 | Novartis Ag | Farmakologisk aktive pyridinderivater og fremgangsmåder til fremstilling deraf |
AU693475B2 (en) | 1993-10-01 | 1998-07-02 | Novartis Ag | Pyrimidineamine derivatives and processes for the preparation thereof |
GB9401182D0 (en) | 1994-01-21 | 1994-03-16 | Inst Of Cancer The Research | Antibodies to EGF receptor and their antitumour effect |
US5559137A (en) | 1994-05-16 | 1996-09-24 | Smithkline Beecham Corp. | Compounds |
PT817775E (pt) | 1995-03-30 | 2002-01-30 | Pfizer | Derivados de quinazolina |
TW449590B (en) | 1995-04-14 | 2001-08-11 | Boehringer Ingelheim Kg | New arylglycinamide derivatives, processes for the manufacture thereof and pharmaceutical compositions containing these compounds |
US5739143A (en) | 1995-06-07 | 1998-04-14 | Smithkline Beecham Corporation | Imidazole compounds and compositions |
IL118544A (en) | 1995-06-07 | 2001-08-08 | Smithkline Beecham Corp | History of imidazole, the process for their preparation and the pharmaceutical preparations containing them |
US5880141A (en) * | 1995-06-07 | 1999-03-09 | Sugen, Inc. | Benzylidene-Z-indoline compounds for the treatment of disease |
HUP9900330A3 (en) | 1995-07-06 | 2001-08-28 | Novartis Ag | Pyrrolopyrimidines and processes for the preparation thereof |
EE03681B1 (et) | 1995-10-06 | 2002-04-15 | Merck & Co., Inc. | Asendatud imidasoolid, millel on vähivastane ja tsütokiine inhibeeriv toime |
AU7482396A (en) | 1995-10-31 | 1997-05-22 | Merck & Co., Inc. | Substituted aryl pyrroles, compositions containing such compounds and methods of use |
EP0859771A4 (en) | 1995-10-31 | 2000-03-15 | Merck & Co Inc | SUBSTITUTED PYRIDYL PYRROLES, COMPOSITIONS CONTAINING SUCH COMPOUNDS AND METHOD OF USE |
WO1997025047A1 (en) | 1996-01-11 | 1997-07-17 | Smithkline Beecham Corporation | Novel cycloalkyl substituded imidazoles |
ZA97175B (en) | 1996-01-11 | 1997-11-04 | Smithkline Beecham Corp | Novel substituted imidazole compounds. |
AP9700912A0 (en) | 1996-01-11 | 1997-01-31 | Smithkline Beecham Corp | Novel cycloalkyl substituted imidazoles |
JP2000503302A (ja) | 1996-01-11 | 2000-03-21 | スミスクライン・ビーチャム・コーポレイション | 新規置換イミダゾール化合物 |
DE19608665A1 (de) | 1996-03-06 | 1997-09-11 | Boehringer Ingelheim Kg | Neue Arylglycinamidderivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Zusammensetzungen |
EP0888335A4 (en) | 1996-03-13 | 2002-01-02 | Smithkline Beecham Corp | NEW PYRIMIDINE COMPOUNDS AND THEIR USE IN THE TREATMENT OF CYTOKININ MEDIATOR DISEASES |
EP0889887A4 (en) | 1996-03-25 | 2003-06-11 | Smithkline Beecham Corp | TREATMENT OF CENTRAL NERVOUS SYSTEM INJURIES |
EP0889888A4 (en) | 1996-03-25 | 2003-01-08 | Smithkline Beecham Corp | NEW TREATMENT OF LESIONS IN THE CENTRAL NERVOUS SYSTEM |
AU727939B2 (en) | 1996-04-03 | 2001-01-04 | Merck & Co., Inc. | A method of treating cancer |
ES2239357T3 (es) | 1996-06-10 | 2005-09-16 | MERCK & CO., INC. | Imidazoles sustituidos que tienen actividad inhibidora de citoquinas. |
WO1998006715A1 (en) | 1996-08-09 | 1998-02-19 | Smithkline Beecham Corporation | Novel piperazine containing compounds |
EP0956018A4 (en) | 1996-08-21 | 2000-01-12 | Smithkline Beecham Corp | IMIDAZOLE COMPOUNDS, COMPOSITIONS CONTAINING THEM AND THEIR USE |
DE19633640C2 (de) | 1996-08-21 | 1999-05-06 | Ford Global Tech Inc | Vorrichtung zur Winkelverstellung einer Welle gegenüber einem Antriebsrad |
WO1998022457A1 (en) | 1996-11-19 | 1998-05-28 | Amgen Inc. | Aryl and heteroaryl substituted fused pyrrole antiinflammatory agents |
JP2000514088A (ja) | 1996-11-20 | 2000-10-24 | メルク エンド カンパニー インコーポレーテッド | グルカゴンアンタゴニストとしてのトリアリール置換イミダゾール |
AR038955A1 (es) | 1996-12-05 | 2005-02-02 | Amgen Inc | Compuestos de pirimidinona y piridona sustituidos y metodos para su uso |
CN1328277C (zh) | 1996-12-05 | 2007-07-25 | 安姆根有限公司 | 取代的嘧啶酮和吡啶酮化合物和它们的应用 |
ZA9711092B (en) | 1996-12-11 | 1999-07-22 | Smithkline Beecham Corp | Novel compounds. |
US6147080A (en) | 1996-12-18 | 2000-11-14 | Vertex Pharmaceuticals Incorporated | Inhibitors of p38 |
EP0964849B1 (en) | 1997-01-29 | 2003-06-04 | Pfizer Inc. | Sulfonyl urea derivatives and their use in the control of interleukin-1 activity |
IL132318A0 (en) | 1997-04-24 | 2001-03-19 | Ortho Mcneil Pharm Inc | Substituted imidazoles useful in the treatment of inflammatory diseases |
AU7132998A (en) | 1997-04-24 | 1998-11-13 | Ortho-Mcneil Corporation, Inc. | Substituted pyrrolopyridines useful in the treatment of inflammatory diseases |
US6235883B1 (en) | 1997-05-05 | 2001-05-22 | Abgenix, Inc. | Human monoclonal antibodies to epidermal growth factor receptor |
ATE292623T1 (de) | 1997-05-07 | 2005-04-15 | Sugen Inc | 2-indolinonderivate als modulatoren der proteinkinase-ativität |
US6514977B1 (en) | 1997-05-22 | 2003-02-04 | G.D. Searle & Company | Substituted pyrazoles as p38 kinase inhibitors |
AU755498B2 (en) | 1997-05-22 | 2002-12-12 | G.D. Searle & Co. | 3(5)-heteroaryl substituted pyrazoles as p38 kinase inhibitors |
WO1998052940A1 (en) | 1997-05-22 | 1998-11-26 | G.D. Searle And Co. | SUBSTITUTED PYRAZOLES AS p38 KINASE INHIBITORS |
CA2288787A1 (en) | 1997-05-22 | 1998-11-26 | G.D. Searle And Co. | Pyrazole derivatives as p38 kinase inhibitors |
CA2291065C (en) | 1997-05-23 | 2010-02-09 | Bayer Corporation | Raf kinase inhibitors |
DE69826695T2 (de) | 1997-05-23 | 2006-02-02 | Bayer Pharmaceuticals Corp., West Haven | Arylharnstoffderivate zur behandlung von inflammatorischen oder immunomodulatorischen erkrankungen |
BR9810007B1 (pt) | 1997-06-12 | 2010-04-06 | compostos, e, derivados da resina de merrifield. | |
EP1023066A4 (en) | 1997-06-13 | 2001-05-23 | Smithkline Beecham Corp | NEW PYRAZOLE AND PYRAZOLINE SUBSTITUTED COMPOUND |
US6093742A (en) | 1997-06-27 | 2000-07-25 | Vertex Pharmaceuticals, Inc. | Inhibitors of p38 |
JP2002515915A (ja) | 1997-06-30 | 2002-05-28 | オーソ−マクニール・フアーマシユーチカル・インコーポレーテツド | 炎症性疾患の治療で有用な2−置換イミダゾール類 |
GB9713726D0 (en) | 1997-06-30 | 1997-09-03 | Ciba Geigy Ag | Organic compounds |
US5939421A (en) | 1997-07-01 | 1999-08-17 | Signal Pharmaceuticals, Inc. | Quinazoline analogs and related compounds and methods for treating inflammatory conditions |
AR016294A1 (es) | 1997-07-02 | 2001-07-04 | Smithkline Beecham Corp | Compuesto de imidazol sustituido, composicion farmaceutica que la contiene, su uso en la fabricacion de un medicamento y procedimiento para supreparacion |
EP1019396A1 (en) | 1997-07-02 | 2000-07-19 | SmithKline Beecham Corporation | Novel cycloalkyl substituted imidazoles |
TW517055B (en) | 1997-07-02 | 2003-01-11 | Smithkline Beecham Corp | Novel substituted imidazole compounds |
US5981710A (en) | 1997-07-21 | 1999-11-09 | Baxter International, Inc. | Therapeutic hemoglobin composition having isotropically increased size |
GB9718913D0 (en) * | 1997-09-05 | 1997-11-12 | Glaxo Group Ltd | Substituted oxindole derivatives |
KR20010024175A (ko) | 1997-09-23 | 2001-03-26 | 돈 리사 로얄 | 시토킨에 의해 매개되는 질환 치료용 아미드 유도체 |
US5975738A (en) | 1997-09-30 | 1999-11-02 | Lsi Logic Corporation | Method for detecting failure in redundant controllers using a private LUN |
EP1041989A4 (en) | 1997-10-08 | 2002-11-20 | Smithkline Beecham Corp | NEW SUBSTITUTED CYCLOALCENYL COMPOUNDS |
PL340541A1 (en) | 1997-11-14 | 2001-02-12 | Sankyo Co | Pyridipyrrole derivative |
JP2002515891A (ja) | 1997-12-19 | 2002-05-28 | スミスクライン・ビーチャム・コーポレイション | 新規なピペリジン含有化合物 |
EP1037639A4 (en) | 1997-12-19 | 2002-04-17 | Smithkline Beecham Corp | HETEROARYL-SUBSTITUTED IMIDAZOLE COMPOUNDS, THEIR PHARMACEUTICAL COMPOSITIONS AND USES |
PT1043995E (pt) | 1997-12-22 | 2007-01-31 | Bayer Pharmaceuticals Corp | Inibição da actividade de p38-quinase utilização de ureias heterocíclicas substituídas com arilo ou heteroarilo |
ES2154252T3 (es) | 1997-12-22 | 2005-12-01 | Bayer Pharmaceuticals Corp. | Inhibicion de quinasa p38 utilizando difenil-ureas simetricas y asimetricas. |
IL136738A0 (en) | 1997-12-22 | 2001-06-14 | Bayer Ag | Inhibition of p38 kinase activity using substituted heterocyclic ureas |
GB9800569D0 (en) | 1998-01-12 | 1998-03-11 | Glaxo Group Ltd | Heterocyclic compounds |
US6147096A (en) | 1998-02-26 | 2000-11-14 | Ortho Mcneil Pharmaceutical, Inc. | Substituted pyrrolobenzimidazoles for treating inflammatory diseases |
CA2325741C (en) | 1998-03-26 | 2007-05-08 | Santen Pharmaceutical Co., Ltd. | Urea derivatives having tnf- .alpha. production inhibitory effects |
DE19815020A1 (de) | 1998-04-03 | 1999-10-07 | Boehringer Ingelheim Pharma | Neue substituierte Indolinone, ihre Herstellung und ihre Verwendung als Arzneimittel |
DE19816624A1 (de) | 1998-04-15 | 1999-10-21 | Boehringer Ingelheim Pharma | Neue substituierte Indolinone, ihre Herstellung und ihre Verwendung als Arzneimittel |
US6316466B1 (en) | 1998-05-05 | 2001-11-13 | Syntex (U.S.A.) Llc | Pyrazole derivatives P-38 MAP kinase inhibitors |
YU67600A (sh) | 1998-05-05 | 2003-07-07 | F.Hofmann - La Roche Ag. | Derivati pirazola kao inhibitori p-38 map kinaze |
MY132496A (en) | 1998-05-11 | 2007-10-31 | Vertex Pharma | Inhibitors of p38 |
JP2002514640A (ja) | 1998-05-14 | 2002-05-21 | ジー・ディー・サール・アンド・カンパニー | p38キナーゼ阻害剤としての1,5−ジアリール置換ピラゾール類 |
SK286247B6 (sk) | 1998-05-15 | 2008-06-06 | Astrazeneca Ab | Benzamidové deriváty, spôsob ich prípravy, farmaceutické prostriedky, ktoré ich obsahujú a ich použitie pri príprave liečiva na liečbu chorobných stavov sprostredkovaných cytokínmi |
CA2328927C (en) | 1998-05-15 | 2008-02-19 | Astrazeneca Ab | Benzamide derivatives for the treatment of diseases mediated by cytokines |
AU760527C (en) | 1998-05-22 | 2004-05-06 | Smithkline Beecham Corporation | Novel 2-alkyl substituted imidazole compounds |
US6340685B1 (en) | 1998-05-22 | 2002-01-22 | Scios, Inc. | Compounds and methods to treat cardiac failure and other disorders |
US6589954B1 (en) | 1998-05-22 | 2003-07-08 | Scios, Inc. | Compounds and methods to treat cardiac failure and other disorders |
ES2258331T3 (es) | 1998-05-22 | 2006-08-16 | Scios Inc. | Compuestos heterociclicos y procedimientos de tratamiento de insuficiencia cardiaca y otros trastornos. |
CA2333157A1 (en) | 1998-05-26 | 1999-12-02 | Smithkline Beecham Corporation | Novel substituted imidazole compounds |
DE19824922A1 (de) | 1998-06-04 | 1999-12-09 | Boehringer Ingelheim Pharma | Neue substituierte Indolinone, ihre Herstellung und ihre Verwendung als Arzneimittel |
JP2002517486A (ja) | 1998-06-12 | 2002-06-18 | バーテックス ファーマシューティカルズ インコーポレイテッド | p38のインヒビター |
WO2000001688A1 (fr) | 1998-07-02 | 2000-01-13 | Sankyo Company, Limited | Composes heteroaryle a cinq elements |
US6207687B1 (en) | 1998-07-31 | 2001-03-27 | Merck & Co., Inc. | Substituted imidazoles having cytokine inhibitory activity |
IL141183A0 (en) | 1998-08-04 | 2002-02-10 | Astrazeneca Ab | Amide derivatives useful as inhibitors of the production of cytokines |
EP1103543A4 (en) | 1998-08-05 | 2005-06-22 | Santen Pharmaceutical Co Ltd | NOVEL UREA DERIVATIVES CONTAINING NITROGENIC AROMATIC HETEROCYCLES |
JP2003525201A (ja) | 1998-08-20 | 2003-08-26 | スミスクライン・ビーチャム・コーポレイション | 新規な置換トリアゾール化合物 |
US6184226B1 (en) | 1998-08-28 | 2001-02-06 | Scios Inc. | Quinazoline derivatives as inhibitors of P-38 α |
WO2000012074A2 (en) | 1998-08-28 | 2000-03-09 | Scios Inc. | Use of piperidines and/or piperazines as inhibitors of p38-alpha kinase |
JP4191825B2 (ja) | 1998-09-10 | 2008-12-03 | あすか製薬株式会社 | 5−アミノイソキサゾール誘導体 |
DE19842833B4 (de) | 1998-09-18 | 2005-04-14 | Merckle Gmbh | 2-Arylalkylthio-imidazole, 2-Arylalkenylthio-imidazole und 2-Arylalkinylthio-imidazole als Entzündungs-Hemmstoffe und Hemmstoffe der Cytokin-Freisetzung |
AR023659A1 (es) | 1998-09-18 | 2002-09-04 | Vertex Pharma | Un compuesto inhibidor de p38, una composicion farmaceutica que lo comprende y el uso de dicha composicion en el tratamiento y prevencion de estados patologicos |
WO2000017175A1 (en) | 1998-09-18 | 2000-03-30 | Vertex Pharmaceuticals Incorporated | INHIBITORS OF p38 |
RU2219171C2 (ru) | 1998-09-25 | 2003-12-20 | Астразенека Аб | Производные амида, способ их получения и фармацевтическая композиция на их основе |
AU763361B2 (en) | 1998-09-25 | 2003-07-17 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Novel substituted indolinones with an inhibitory effect on various kinases and cyclin/CDK complexes |
WO2000020402A1 (en) | 1998-10-01 | 2000-04-13 | Astrazeneca Ab | Chemical compounds |
EP1261334A1 (en) | 1998-10-20 | 2002-12-04 | Omeros Corporation | Irrigation solution containing mapk inhibitors and their use for treating pain and inflammation |
WO2000026209A1 (en) | 1998-11-03 | 2000-05-11 | Novartis Ag | Anti-inflammatory 4-phenyl-5-pyrimidinyl-imidazoles |
EP1126852B1 (en) | 1998-11-04 | 2004-01-21 | SmithKline Beecham Corporation | Pyridin-4-yl or pyrimidin-4-yl substituted pyrazines |
CZ20011759A3 (cs) | 1998-11-19 | 2002-01-16 | Warner-Lambert Company | N-[4-(3-chlor-4-fluor-fenylamino)-7-(3-morfolin-4-yl-propoxy)-chinazolin-6-yl]-akrylamid, ireversibilní inhibitor tyrosin-kinas |
ES2219092T3 (es) | 1998-11-20 | 2004-11-16 | G.D. Searle Llc | Proceso para fabricar pirazoles 5-substituidos usando ditietanos. |
US6350744B1 (en) | 1998-11-20 | 2002-02-26 | Merck & Co., Inc. | Compounds having cytokine inhibitory activity |
US6387641B1 (en) | 1998-12-16 | 2002-05-14 | Vertex Pharmaceuticals Incorporated | Crystallized P38 complexes |
JP4634613B2 (ja) | 1998-12-16 | 2011-02-16 | アベンティス・フアーマ・リミテッド | ヘテロアリール環状アセタール類 |
WO2000039116A1 (fr) | 1998-12-25 | 2000-07-06 | Teikoku Hormone Mfg. Co., Ltd. | Derives d'aminopyrazole |
EP1158985B1 (en) | 1999-01-13 | 2011-12-28 | Bayer HealthCare LLC | OMEGA-CARBOXY ARYL SUBSTITUTED DIPHENYL UREAS AS p38 KINASE INHIBITORS |
UA73492C2 (en) | 1999-01-19 | 2005-08-15 | Aromatic heterocyclic compounds as antiinflammatory agents | |
GB9904933D0 (en) * | 1999-03-04 | 1999-04-28 | Glaxo Group Ltd | Compounds |
RU2242474C2 (ru) | 1999-03-12 | 2004-12-20 | Бёрингер Ингельхайм Фармасьютиклз, Инк. | Соединения, пригодные в качестве противовоспалительных агентов |
WO2000055152A1 (en) | 1999-03-12 | 2000-09-21 | Boehringer Ingelheim Pharmaceuticals, Inc. | Aromatic heterocyclic compounds as anti-inflammatory agents |
CN1178932C (zh) | 1999-03-17 | 2004-12-08 | 阿斯特拉曾尼卡有限公司 | 酰胺衍生物 |
ES2246830T3 (es) | 1999-03-17 | 2006-03-01 | Astrazeneca Ab | Derivados de amida. |
GB9906566D0 (en) | 1999-03-23 | 1999-05-19 | Zeneca Ltd | Chemical compounds |
CO5170501A1 (es) | 1999-04-14 | 2002-06-27 | Novartis Ag | AZOLES SUSTITUIDOS UTILES PARA EL TRATAMIENTO DE ENFERMEDADES MEDIADAS POR TNFa eIL-1 Y ENFERMEDADES DEL METABOLISMO OSEO |
US6492516B1 (en) | 1999-05-14 | 2002-12-10 | Merck & Co., Inc. | Compounds having cytokine inhibitory activity |
CA2372567A1 (en) | 1999-05-21 | 2000-11-30 | Scios Inc. | Indole-type derivatives as inhibitors of p38 kinase |
DE19924401A1 (de) | 1999-05-27 | 2000-11-30 | Boehringer Ingelheim Pharma | Neue substituierte Indolinone, ihre Herstellung und ihre Verwendung als Arzneimittel |
MEP45508A (en) | 1999-06-21 | 2011-02-10 | Boehringer Ingelheim Pharma | Bicyclic heterocycles, medicaments containing these compounds, their use and methods for the production thereof |
US6403596B1 (en) | 1999-06-28 | 2002-06-11 | Merck & Co., Inc. | Substituted pyridones having cytokine inhibitory activity |
US6566554B1 (en) | 1999-07-16 | 2003-05-20 | Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske Fabrik Produktionsaktieselskab) | Aminobenzophenones as inhibitors of IL-1β and TNF-α |
ATE277897T1 (de) | 1999-07-16 | 2004-10-15 | Leo Pharma As | Aminobenzophenone als inhibitoren von il-1beta und tnf-alpha |
US6624199B1 (en) | 1999-07-16 | 2003-09-23 | Leo Pharmaceuticals Products Ltd. A/S | Aminobenzophenones |
US6750253B1 (en) | 1999-07-16 | 2004-06-15 | Leo Pharmaceutical Products Ltd. A/S | Aminobenzophenones as inhibitors of il-1β and tnf-α |
US6555710B1 (en) | 1999-07-16 | 2003-04-29 | Leo Pharmaceutical Products Ltd A/S Lovens Kemiske Fabrik Produktionsaktieselskab | Aminobenzophenones as inhibitors of IL-1 β and TNF-α |
EP1212318B1 (de) | 1999-08-27 | 2006-01-25 | Boehringer Ingelheim Pharma GmbH & Co.KG | Substituierte indolinone als tyrosinkinase inhibitoren |
UA75054C2 (uk) * | 1999-10-13 | 2006-03-15 | Бьорінгер Інгельхайм Фарма Гмбх & Ко. Кг | Заміщені в положенні 6 індолінони, їх одержання та їх застосування як лікарського засобу |
JP2003511055A (ja) | 1999-10-13 | 2003-03-25 | レオ・ファーマ・アクティーゼルスカブ | Msk1に作用する物質をスクリーニングする方法 |
DE19949209A1 (de) | 1999-10-13 | 2001-04-19 | Boehringer Ingelheim Pharma | In 5-Stellung substituierte Indolinone, ihre Herstellung und ihre Verwendung als Arzneimittel |
GB9924092D0 (en) | 1999-10-13 | 1999-12-15 | Zeneca Ltd | Pyrimidine derivatives |
BR0015243A (pt) | 1999-10-21 | 2002-07-16 | Hoffmann La Roche | Heterociclos de nitrogênio bicìclico substituìdos por heteroalquilamino como inibidores da proteìna cinase p38 |
ES2277858T3 (es) | 1999-10-21 | 2007-08-01 | F. Hoffmann-La Roche Ag | Heterociclos de nitrogeno biciclicos alquilamino sustituidos como inhibidores de proteina kinasa p38. |
CN1255406C (zh) | 1999-11-10 | 2006-05-10 | 奥索-麦克尼尔药品公司 | 取代的2-芳基-3-(杂芳基)-咪唑并[1,2-a]嘧啶类化合物以及相关的药物组合物和方法 |
UA74803C2 (uk) | 1999-11-11 | 2006-02-15 | Осі Фармасьютікалз, Інк. | Стійкий поліморф гідрохлориду n-(3-етинілфеніл)-6,7-біс(2-метоксіетокси)-4-хіназолінаміну, спосіб його одержання (варіанти) та фармацевтичне застосування |
US6492393B1 (en) | 1999-11-16 | 2002-12-10 | Boehringer Ingelheim Pharmaceuticals, Inc. | Compounds useful as anti-inflammatory agents |
EP1233950B1 (en) | 1999-11-23 | 2005-10-05 | Smithkline Beecham Corporation | 3,4-DIHYDRO-(1H)QUINAZOLIN-2-ONE COMPOUNDS AS CSBP/P39 kINASE INHIBITORS |
US7053099B1 (en) | 1999-11-23 | 2006-05-30 | Smithkline Beecham Corporation | 3,4-dihydro-(1H)quinazolin-2-one compounds as CSBP/p38 kinase inhibitors |
WO2001037837A1 (en) | 1999-11-23 | 2001-05-31 | Smithkline Beecham Corporation | 3,4-DIHYDRO-(1H)-QUINAZOLIN-2-ONES AND THEIR USE AS CSBP/p38 KINASE INHIBITORS |
JP2003514900A (ja) | 1999-11-23 | 2003-04-22 | スミスクライン・ビーチャム・コーポレイション | CSBP/p38キナーゼ阻害剤としての3,4−ジヒドロ−(1H)−キナゾリン−2−オン化合物 |
CZ20021703A3 (cs) | 1999-11-30 | 2003-06-18 | Pfizer Products Inc. | 2,4-Diaminopyrimidinové sloučeniny užitečné jako imunosupresiva |
PL356049A1 (en) | 1999-12-06 | 2004-06-14 | Leo Pharma A/S | Aminobenzophenones as inhibitors of il-1beta and tnf-alpha |
US6602872B1 (en) | 1999-12-13 | 2003-08-05 | Merck & Co., Inc. | Substituted pyridazines having cytokine inhibitory activity |
AU2735201A (en) | 1999-12-28 | 2001-07-09 | Pharmacopeia, Inc. | Pyrimidine and triazine kinase inhibitors |
DE20002820U1 (de) | 2000-02-16 | 2000-05-25 | Igus Gmbh | Energieführungskette |
EP1259486A1 (en) | 2000-02-23 | 2002-11-27 | Iconix Pharmaceuticals, Inc. | Pyridine-amidines as modulators of p38 map kinase |
WO2001064676A2 (en) | 2000-02-28 | 2001-09-07 | Scios, Inc. | INHIBITORS OF p38-α KINASE |
AR035851A1 (es) | 2000-03-28 | 2004-07-21 | Wyeth Corp | 3-cianoquinolinas, 3-ciano-1,6-naftiridinas y 3-ciano-1,7-naftiridinas como inhibidoras de proteina quinasas |
MXPA02009855A (es) | 2000-04-08 | 2003-03-27 | Boehringer Ingelheim Pharma | Heterociclos biciclicos, medicamentos que contienen estos compuestos, su empleo y procedimientos para su preparacion. |
DE10042058A1 (de) | 2000-08-26 | 2002-03-07 | Boehringer Ingelheim Pharma | Bicyclische Heterocyclen, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
DE10042059A1 (de) | 2000-08-26 | 2002-03-07 | Boehringer Ingelheim Pharma | Bicyclische Heterocyclen, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
DE10042062A1 (de) | 2000-08-26 | 2002-03-07 | Boehringer Ingelheim Pharma | Bicyclische Heterocyclen, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Hertellung |
DE10042060A1 (de) | 2000-08-26 | 2002-03-07 | Boehringer Ingelheim Pharma | Bicyclische Heterocyclen, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
DE10051320A1 (de) | 2000-10-17 | 2002-04-25 | Boehringer Ingelheim Pharma | Neue Neurokininantagonisten, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Zusammensetzungen |
DE10054019A1 (de) | 2000-11-01 | 2002-05-23 | Boehringer Ingelheim Pharma | Neue substituierte Indolinone, ihre Herstellung und ihre Verwendung als Arzneimittel |
US6638965B2 (en) | 2000-11-01 | 2003-10-28 | Boehringer Ingelheim Pharma Kg | Substituted indolinones, preparation thereof and their use as pharmaceutical compositions |
DE10063435A1 (de) | 2000-12-20 | 2002-07-04 | Boehringer Ingelheim Pharma | Chinazolinderviate,diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
DE10117204A1 (de) | 2001-04-06 | 2002-10-10 | Boehringer Ingelheim Pharma | In 6-Stellung substituierte Indolinone, ihre Herstellung und ihre Verwendung als Arzneimittel |
PL371188A1 (en) | 2002-03-30 | 2005-06-13 | Boehringer Ingelheim Pharma Gmbh & Co.Kg | 4-(n-phenylamino)-quinazolines / quinolines as tyrosine kinase inhibitors |
DE10233500A1 (de) | 2002-07-24 | 2004-02-19 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | 3-Z-[1-(4-(N-((4-Methyl-piperazin-1-yl)-methylcarbonyl)-N-methyl-amino)-anilino)-1-phenyl-methylen]-6-methoxycarbonyl-2-indolinon-Monoethansulfonat und dessen Verwendung als Arzneimittel |
DE10237423A1 (de) * | 2002-08-16 | 2004-02-19 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Verwendung von LCK-Inhibitoren für die Behandlung von immunologischen Erkrankungen |
US20040204458A1 (en) | 2002-08-16 | 2004-10-14 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Use of Lck inhibitors for treatment of immunologic diseases |
US7148249B2 (en) | 2002-09-12 | 2006-12-12 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Indolinones substituted by heterocycles, the preparation thereof and their use as medicaments |
US20050043233A1 (en) | 2003-04-29 | 2005-02-24 | Boehringer Ingelheim International Gmbh | Combinations for the treatment of diseases involving cell proliferation, migration or apoptosis of myeloma cells or angiogenesis |
US20060154939A1 (en) | 2004-12-24 | 2006-07-13 | Boehringer Ingelheim International Gmbh | Medicaments for the Treatment or Prevention of Fibrotic Diseases |
PE20060777A1 (es) | 2004-12-24 | 2006-10-06 | Boehringer Ingelheim Int | Derivados de indolinona para el tratamiento o la prevencion de enfermedades fibroticas |
PE20061155A1 (es) | 2004-12-24 | 2006-12-16 | Boehringer Ingelheim Int | Derivados de indolinona como agentes para el tratamiento o la prevencion de enfermedades fibroticas |
RS57035B1 (sr) | 2008-06-06 | 2018-05-31 | Boehringer Ingelheim Int | Farmaceutska kombinacija |
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Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6762180B1 (en) * | 1999-10-13 | 2004-07-13 | Boehringer Ingelheim Pharma Kg | Substituted indolines which inhibit receptor tyrosine kinases |
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