KR101235094B1 - 섬유성 질환의 치료 또는 예방용 인돌리논 유도체 - Google Patents
섬유성 질환의 치료 또는 예방용 인돌리논 유도체 Download PDFInfo
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- KR101235094B1 KR101235094B1 KR1020077017058A KR20077017058A KR101235094B1 KR 101235094 B1 KR101235094 B1 KR 101235094B1 KR 1020077017058 A KR1020077017058 A KR 1020077017058A KR 20077017058 A KR20077017058 A KR 20077017058A KR 101235094 B1 KR101235094 B1 KR 101235094B1
- Authority
- KR
- South Korea
- Prior art keywords
- phenyl
- methylene
- indolinone
- anilino
- amino
- Prior art date
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- 238000011282 treatment Methods 0.000 title abstract description 20
- 230000003176 fibrotic effect Effects 0.000 title abstract description 14
- 201000010099 disease Diseases 0.000 title abstract description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title abstract description 10
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical class C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 title abstract description 7
- 230000002265 prevention Effects 0.000 title description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 48
- -1 4- (N-((4-methyl-piperazin-1-yl) -methylcarbonyl) -N-methyl-amino) -anilino Chemical group 0.000 claims description 305
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 96
- 125000000217 alkyl group Chemical group 0.000 description 80
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 60
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- PWDPLHOKCYLVIC-RQZHXJHFSA-N methyl (3z)-3-[[4-[acetyl-[2-(dimethylamino)ethyl]amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(CCN(C)C)C(C)=O)C=C1 PWDPLHOKCYLVIC-RQZHXJHFSA-N 0.000 description 2
- 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 description 2
- 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 description 2
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- VDPRXJJHNKENAW-BZZOAKBMSA-N ethyl (3z)-2-oxo-3-[1-[4-(piperidin-1-ylmethyl)anilino]butylidene]-1h-indole-6-carboxylate Chemical compound O=C/1NC2=CC(C(=O)OCC)=CC=C2C\1=C(/CCC)NC(C=C1)=CC=C1CN1CCCCC1 VDPRXJJHNKENAW-BZZOAKBMSA-N 0.000 description 1
- JRQSJOLNYVLGCF-GDNBJRDFSA-N ethyl (3z)-2-oxo-3-[[4-(2h-tetrazol-5-yl)anilino]methylidene]-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C\NC(C=C1)=CC=C1C1=NN=NN1 JRQSJOLNYVLGCF-GDNBJRDFSA-N 0.000 description 1
- LHPSZPYVCWLGAN-QNGOZBTKSA-N ethyl (3z)-2-oxo-3-[[4-(piperidin-1-ylmethyl)anilino]methylidene]-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C\NC(C=C1)=CC=C1CN1CCCCC1 LHPSZPYVCWLGAN-QNGOZBTKSA-N 0.000 description 1
- OWOPKDUSNNZHBW-RQZHXJHFSA-N ethyl (3z)-2-oxo-3-[[4-[(3-oxopiperazin-1-yl)methyl]anilino]-phenylmethylidene]-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=C1CN1CCNC(=O)C1 OWOPKDUSNNZHBW-RQZHXJHFSA-N 0.000 description 1
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- ILJNNOVJCOAWGV-RQZHXJHFSA-N ethyl (3z)-2-oxo-3-[phenyl-(4-pyridin-3-ylanilino)methylidene]-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=CC=CN=C1 ILJNNOVJCOAWGV-RQZHXJHFSA-N 0.000 description 1
- ZRMPMVMYOOTMOO-RQZHXJHFSA-N ethyl (3z)-2-oxo-3-[phenyl-(4-pyridin-4-ylanilino)methylidene]-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=CC=NC=C1 ZRMPMVMYOOTMOO-RQZHXJHFSA-N 0.000 description 1
- WJWAIQVEXSMNLI-IZHYLOQSSA-N ethyl (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)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CN1C=NC=N1 WJWAIQVEXSMNLI-IZHYLOQSSA-N 0.000 description 1
- PNRLMDYYUCCHOB-ZIADKAODSA-N ethyl (3z)-2-oxo-3-[phenyl-[4-(2-piperidin-1-ylethyl)anilino]methylidene]-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=C1CCN1CCCCC1 PNRLMDYYUCCHOB-ZIADKAODSA-N 0.000 description 1
- NWVDZWOTZGZLBZ-DQRAZIAOSA-N ethyl (3z)-2-oxo-3-[phenyl-[4-(2h-tetrazol-5-yl)anilino]methylidene]-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=NN=NN1 NWVDZWOTZGZLBZ-DQRAZIAOSA-N 0.000 description 1
- NWDQBTVOPGCYBA-RQZHXJHFSA-N ethyl (3z)-2-oxo-3-[phenyl-[4-(piperazin-1-ylmethyl)anilino]methylidene]-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=C1CN1CCNCC1 NWDQBTVOPGCYBA-RQZHXJHFSA-N 0.000 description 1
- IXLWLINBDPVBIF-QPLCGJKRSA-N ethyl (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)OCC)C=C2NC\1=O IXLWLINBDPVBIF-QPLCGJKRSA-N 0.000 description 1
- KWRATKYHTNEHDF-RQZHXJHFSA-N ethyl (3z)-2-oxo-3-[phenyl-[4-(pyrrolidin-1-ylmethyl)anilino]methylidene]-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=C1CN1CCCC1 KWRATKYHTNEHDF-RQZHXJHFSA-N 0.000 description 1
- FONNKMIXGFHFRV-RQZHXJHFSA-N ethyl (3z)-2-oxo-3-[phenyl-[4-(thiomorpholin-4-ylmethyl)anilino]methylidene]-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=C1CN1CCSCC1 FONNKMIXGFHFRV-RQZHXJHFSA-N 0.000 description 1
- GMRUCQGFMCXZCE-IZHYLOQSSA-N ethyl (3z)-2-oxo-3-[phenyl-[4-(triazol-1-ylmethyl)anilino]methylidene]-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CN1C=CN=N1 GMRUCQGFMCXZCE-IZHYLOQSSA-N 0.000 description 1
- PXQKFKVOLJRXCJ-IZHYLOQSSA-N ethyl (3z)-2-oxo-3-[phenyl-[4-(triazol-2-ylmethyl)anilino]methylidene]-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=C1CN1N=CC=N1 PXQKFKVOLJRXCJ-IZHYLOQSSA-N 0.000 description 1
- QYLAOEXGMQWKHB-DQRAZIAOSA-N ethyl (3z)-2-oxo-3-[phenyl-[4-(trifluoromethyl)anilino]methylidene]-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(C(F)(F)F)C=C1 QYLAOEXGMQWKHB-DQRAZIAOSA-N 0.000 description 1
- FEKDGMBDLGAOAF-KTMFPKCZSA-N ethyl (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)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1N(C(C)C)C(=O)CN1CCNCC1 FEKDGMBDLGAOAF-KTMFPKCZSA-N 0.000 description 1
- MIEFLTZYAPOBFN-MVJHLKBCSA-N ethyl (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)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1N(C(C)C)C(=O)CN1CCCCC1 MIEFLTZYAPOBFN-MVJHLKBCSA-N 0.000 description 1
- QVQIRKMPBLECLK-QPLCGJKRSA-N ethyl (3z)-2-oxo-3-[phenyl-[4-[(propan-2-ylamino)methyl]anilino]methylidene]-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CNC(C)C)C=C1 QVQIRKMPBLECLK-QPLCGJKRSA-N 0.000 description 1
- 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
- ASVVTHLXDFAGGY-LNVKXUELSA-N ethyl (3z)-3-[1-[4-[2-(dimethylamino)ethyl-methylsulfonylamino]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(CCN(C)C)S(C)(=O)=O)C=C1 ASVVTHLXDFAGGY-LNVKXUELSA-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
- 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
- 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
- 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
- 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
- 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
- ZKOGBRAZSIKDIV-ZIADKAODSA-N ethyl (3z)-3-[[4-(cyclohexylidenemethyl)anilino]-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=C1CCCCC1 ZKOGBRAZSIKDIV-ZIADKAODSA-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
- 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
- RSSKKXOEKNCIIC-IZHYLOQSSA-N ethyl (3z)-3-[[4-[(2-methylpropan-2-yl)oxycarbonyl]anilino]-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(=O)OC(C)(C)C)C=C1 RSSKKXOEKNCIIC-IZHYLOQSSA-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
- 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
- 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
- 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
- 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
- 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
- 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
- HZYMAEIFYBYQOG-ZIADKAODSA-N ethyl (3z)-3-[[4-[[(2-methylpropan-2-yl)oxycarbonyl-propylamino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(CN(CCC)C(=O)OC(C)(C)C)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OCC)C=C2NC\1=O HZYMAEIFYBYQOG-ZIADKAODSA-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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- LIUUNDYTFMPKFZ-FLWNBWAVSA-N ethyl (3z)-3-[[4-[[butyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(CN(CCCC)C(=O)OC(C)(C)C)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OCC)C=C2NC\1=O LIUUNDYTFMPKFZ-FLWNBWAVSA-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
- 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
- UCBVEGIXZIFMFH-DQSJHHFOSA-N ethyl (3z)-3-[[4-[[ethyl-[(2-methylpropan-2-yl)oxycarbonyl]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(=O)OC(C)(C)C)C=C1 UCBVEGIXZIFMFH-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
- IQCQBGHIMSVBKU-RQZHXJHFSA-N ethyl (3z)-3-[[4-[[methyl(propyl)amino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(CN(C)CCC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OCC)C=C2NC\1=O IQCQBGHIMSVBKU-RQZHXJHFSA-N 0.000 description 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
- ITXCOEOGWLWEBN-ZIADKAODSA-N ethyl (3z)-3-[[4-[[methyl-[2-[(2-methylpropan-2-yl)oxycarbonylamino]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)\NC1=CC=C(CN(C)CCNC(=O)OC(C)(C)C)C=C1 ITXCOEOGWLWEBN-ZIADKAODSA-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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
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- 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
- 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
- PJYLAPUQQYSUKA-RQZHXJHFSA-N methyl (3z)-2-oxo-3-[phenyl-[4-(piperidin-1-ylmethyl)anilino]methylidene]-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CN1CCCCC1 PJYLAPUQQYSUKA-RQZHXJHFSA-N 0.000 description 1
- WFWFAKWTVKMAJE-IZHYLOQSSA-N methyl (3z)-2-oxo-3-[phenyl-[4-(propylaminomethyl)anilino]methylidene]-1h-indole-6-carboxylate Chemical compound C1=CC(CNCCC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O WFWFAKWTVKMAJE-IZHYLOQSSA-N 0.000 description 1
- 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
- IXOHHHGFPNGORW-UQQQWYQISA-N methyl (3z)-3-[1-[4-[[(4-chlorophenyl)methyl-methylamino]methyl]anilino]ethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(/C)NC(C=C1)=CC=C1CN(C)CC1=CC=C(Cl)C=C1 IXOHHHGFPNGORW-UQQQWYQISA-N 0.000 description 1
- UKDNXXZAGVDGLC-ATJXCDBQSA-N methyl (3z)-3-[1-[4-[[2-(dimethylamino)acetyl]-methylamino]anilino]butylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C/1NC2=CC(C(=O)OC)=CC=C2C\1=C(/CCC)NC1=CC=C(N(C)C(=O)CN(C)C)C=C1 UKDNXXZAGVDGLC-ATJXCDBQSA-N 0.000 description 1
- VAHWEVGCUFXVQK-STZFKDTASA-N methyl (3z)-3-[1-[4-[[2-(dimethylamino)acetyl]-methylamino]anilino]ethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(/C)NC1=CC=C(N(C)C(=O)CN(C)C)C=C1 VAHWEVGCUFXVQK-STZFKDTASA-N 0.000 description 1
- 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
- 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
- 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
- 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
- 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
- AZLHTYINGAUYFA-FCQUAONHSA-N methyl (3z)-3-[[4-(methylaminomethyl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(CNC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O AZLHTYINGAUYFA-FCQUAONHSA-N 0.000 description 1
- IDWZQYHNNILFMO-QPLCGJKRSA-N methyl (3z)-3-[[4-(morpholin-4-ylmethyl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CN1CCOCC1 IDWZQYHNNILFMO-QPLCGJKRSA-N 0.000 description 1
- 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
- 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
- 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
- UEGJTOOVYCHRTA-VHXPQNKSSA-N methyl (3z)-3-[[4-[(2-methylpropan-2-yl)oxycarbonyl]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(=O)OC(C)(C)C)C=C1 UEGJTOOVYCHRTA-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
- 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
- DXKISNXMYHOQJA-DQSJHHFOSA-N methyl (3z)-3-[[4-[1-amino-4-[(2-methylpropan-2-yl)oxycarbonylamino]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)CCCNC(=O)OC(C)(C)C)C=C1 DXKISNXMYHOQJA-DQSJHHFOSA-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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- VBLVPTZXOOSQHZ-QPLCGJKRSA-N methyl (3z)-3-[[4-[[2-(dimethylamino)acetyl]-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CN(C)C)C=C1 VBLVPTZXOOSQHZ-QPLCGJKRSA-N 0.000 description 1
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- YLTPSYXBPYWAEK-DQSJHHFOSA-N methyl (3z)-3-[[4-[[methyl-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]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(=O)OC(C)(C)C)C=C1 YLTPSYXBPYWAEK-DQSJHHFOSA-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
- 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
- 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
- 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
- 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
- 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
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Abstract
Description
본 발명은 6 위치에서 치환된 화학식 I의 인돌리논, 및 이의 토오토머, 입체이성체, 에난티오머, 혼합물 및 염, 특히 생리학적으로 허용되는 염의 신규한 용도에 관한 것이다.
상기 화학식 I의 화합물, 및 이의 토오토머, 디아스테레오머, 에난티오머, 혼합물 및 염, 특히 생리학적으로 허용되는 염은 WO 제01/27081호 및 WO 제04/13099호에 중요한 약리학적 특성, 특히 다양한 키나제, 특히 VEGFR2, PDGFRα, PDGFRβ, FGFR1, FGFR3, EGFR, HER2, IGF1R 및 HGFR와 같은 수용체 티로신 키나제 뿐만 아니라 및 특정한 사이클린(A, B1, B2, C, D1, D2, D3, E, F, G1, G2, H, I 및 K)을 갖는 CDK1, CDK2, CDK3, CDK4, CDK5, CDK6, CDK7, CDK8 및 CDK9과 같은 CDK(사이클린 의존 키나제) 복합체 및 바이러스성 사이클린[참조: L. Mengtao, J. Virology 71(3), 1984-1991(1997)]에 대해, 및 배양된 사람 세포, 특히 내피 세포의 증식에 대해, 예를 들면, 혈관 생성에서, 또한 다른 세포, 특히 종양 세포의 증식에 대해 억제 효과를 갖는 것으로 기재되어 있다.
그러나, 당해 화합물은, 본 발명에 언급된 이들 화합물의 섬유성 질환의 치료 또는 예방 용도에 대해서는 기재되어 있지 않다.
리모델링은 몸 전체의 많은 조직에서 관찰되는 조직 손상 및 염증에 대한 통상의 반응이다. 염증의 소실 및 조직 손상의 회복 이후, 조직은 통상적으로 이의 원래의 상태로 돌아간다. 조절되지 않은 과다한 조직 회복, 또는 더 이상 요구되지 않는 경우의 리모델링 중단의 실패는 섬유증이라고 알려진 병태를 일으킨다. 섬유증은 세포외 기질 성분의 과다한 침착 및 섬유모세포의 과다 성장으로 특징지어진다. 섬유증은 모든 조직에서 일어날 수 있지만 폐, 피부, 소화관, 신장 및 간을 포함하여 화학적 및 생물학적 손상에 자주 노출되는 장기에 특히 널리 존재한다[참조: 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]. 섬유증은 종종 장기의 통상적인 기능(들)을 심각하게 손상시키고, 많은 섬유성 질환은 사실상 생명을 위협하거나 심각하게 변형시키는, 특발성 폐 섬유증(idiopathic pulmonary fibrosis, IPF), 간경화증, 피부 경화증 또는 신장 섬유증과 같은 것들이다. 이러한 질환의 치료 선택은 종종 위험하고 비싼 과정인, 장기 이식에 한정된다.
문헌의 많은 부분은 섬유증의 유도 및 지속에서의 성장 인자 계열인 혈소판-유래 성장인자(PDGF), 섬유모세포 성장 인자(FGF), 혈관 내피 세포 성장 인자(VEGF), 표피 성장 인자(EGF) 및 전환 성장 인자 베타(TGFb)를 포함한다[참조: Levitzki, Cytokine Growth Factor Rev, 2004, 15(4):229-35; Strutz et al., Kidney Intl, 2000, 57:1521-38; Strutz et al., 2003, Springer Semin Immunopathol, 24:459-76; Rice et al., 1999, Amer J Pathol, 155(1):213-221; Broekelmann et al., 1991, Proc Nat Acad Sci, 88:6642-6; Wynn, 2004, Nat Rev Immunol, 4(8):583-94].
PDGF, EGF 및 FGF 계열 구성원은 평활근세포, 근육모세포 및 섬유모세포와 같은 중간엽세포(mesenchymal cells)에 대한 효능있는 미토겐이고[참조: 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], 섬유증에서 통상의 조직을 대신하는 해당 세포는 조직 리모델링에서 역할을 하는 것으로 여겨진다[참조: 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, 2000, 21:385-95].
PDGF 억제는 실험 모델에서의 간 섬유증 및 폐 섬유증 모두를 약화시키고, 이는 서로 다른 장기에서의 섬유증이 공통된 기원을 갖는다는 것을 암시한다[참조: Borkham-Kamphorst et al., 2004, Biochem Biophys Res Commun; Rice et al., 1999, Amer J Pathol, 155(1):213-221]. EGF 수용체 키나제 억제제는 또한 이러한 폐 섬유증 모델에서 활성이다. 마우스의 췌장 섬에서의, EGF 계열 구성원인 HB-EGF의 3중 과발현은 외분비 및 내분비 구획 모두에서 섬유증을 일으키기에 충분하다[참조: Means et al., 2003, Gastroenterology, 124(4):1020-36].
유사하게, FGF1/FGF2-결핍 마우스는 만성 사염화탄소(CCl4) 노출 이후 급격하게 감소된 간 섬유증을 보인다[참조: Yu et al., 2003, Am J Pathol, 163(4):1653-62]. FGF 발현은 사이질 흉터 형성과 강하게 연동된 사람 신장 사이질 섬유증 뿐만 아니라[참조: Strutz et al., 2000, Kidney Intl, 57:1521-38], 실험적 폐 섬유증 모델에서[참조: Barrios et al., 1997, Am J Physiol, 273 (2 Pt 1):L451-8] 증가되고, 이는 다시 다양한 조직에서의 섬유증이 공통된 기원을 갖는다는 생각에 확신을 준다.
추가로, VEGF의 증가된 수준이 천식이 있는 사람에서의 몇몇 연구에서 관찰되었다[참조: Hoshino et al., 2001, J Allergy Clin Immunol 107:1034-39; Hoshino et al., 2001, J Allergy Clin Immunol 107:295-301; Kanazawa et al., 2002, Thorax 57:885-8; Asai et al., J Allergy Clin Immunol 110:571-5, 2002; Kanazawa et al., 2004, Am J Respir Crit Care Med, 169:1125-30]. 유전자 도입 마우스 모델에서의 VEGF의 유도성 발현은 천식과 유사한 표현형, 부종, 혈관 형성 및 평활근 과다 형성을 유발한다[참조: Lee et al., 2004, Nature Med 10:1095-1103].
마지막으로, TGFb는 피브로넥틴 및 콜라겐을 포함하는 세포외 기질 단백질의 생산을 자극하고 많은 조직의 섬유증에서 중요한 역할을 하는 것으로 여겨진다[참조: 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]. TGFb 생산 및 신호 전달 경로의 억제제는 많은 동물 모델의 섬유증에서 활성이다[참조: Wang et al., 2002, Exp Lung Res, 28:405-17; Laping, 2003, Curr Opin Pharmacol, 3(2):204-8].
상기 요약한 바와 같이, 몇몇 성장 인자는 섬유증에서 상향조절되고 단일 인자의 억제는 섬유증 모델에서 섬유증의 심각성을 감소시키는 것으로 보인다.
발명의 요약
놀랍게도, 본 발명에 이르러 상기 화학식 I의 화합물이 특정 섬유성 질환의 치료 또는 예방에 효과적이라는 것이 밝혀졌다.
따라서 본 발명은 특정 섬유성 질환의 치료 또는 예방용 약제의 제조를 위한 상기 화학식 I의 화합물의 용도에 관한 것이다.
본 발명은 또한 상기 화학식 I의 화합물과 약제학적으로 적합한 담체를 함께 포함하는 약제학적 조성물을 특정 섬유성 질환의 치료 또는 예방을 필요로 하는 환자에게 투여하여, 특정 섬유성 질환을 치료 또는 예방하는 방법에 관한 것이다. 용어 "환자"는 포유류 동물의 몸, 특히 사람의 몸을 포함하는 것을 나타낸다.
본 발명은 추가로 상기 화학식 I의 화합물을 단독으로 또는 하나 이상의 추가적인 치료 약제와 병용하여 포함하는 특정 섬유성 질환의 치료 또는 예방용 약제학적 조성물에 관한 것이다.
본 발명에 따라, 화학식 I의 화합물은 하기 화학식의 화합물이다.
화학식 I
위의 화학식 I에서,
X는 산소 또는 황 원자이고,
R1은 수소 원자 또는 프로드럭 그룹, 예를 들면, C1-4-알콕시카보닐 또는 C2-4-알카노일 그룹이고,
R2는 카복시 그룹, 직쇄 또는 측쇄 C1-6-알콕시-카보닐 그룹, C4-7-사이클로알콕시-카보닐 또는 아릴옥시카보닐 그룹,
삭제
알킬 잔기에서 페닐, 헤테로아릴, 카복시, C1-3-알콕시-카보닐, 아미노카보닐, C1-3-알킬아미노-카보닐 또는 디-(C1-3-알킬)-아미노카보닐 그룹에 의해 말단 치환된 직쇄 또는 측쇄 C1-6-알콕시-카보닐 그룹,
알킬 잔기에서 염소 원자, 또는 하이드록시, C1-3-알콕시, 아미노, C1-3-알킬아미노 또는 디-(C1-3-알킬)-아미노 그룹에 의해 말단 치환된 직쇄 또는 측쇄 C2-6-알콕시-카보닐 그룹, 또는
아미노카보닐 또는 메틸 아미노카보닐 그룹, 또는 에틸 그룹의 2 위치에서 하이드록시 또는 C1-3-알콕시 그룹에 의해 임의로 치환된 에틸아미노카보닐 그룹 또는 디-(C1-2-알킬)-아미노카보닐 그룹이고,
R3은 수소 원자, C1-6-알킬, C3-7-사이클로알킬, 트리플루오로메틸 또는 헤테로아릴 그룹,
삭제
페닐 또는 나프틸 그룹, 또는 플루오르, 염소, 브롬 또는 요오드 원자, 트리플루오로메틸, C1-3-알킬 또는 C1-3-알콕시 그룹에 의해 1 또는 2치환된 페닐 또는 나프틸 그룹이고,
여기서, 2치환되는 경우 치환체는 동일하거나 상이하고, 상기 언급된 치환되지 않은 페닐 및 나프틸 그룹 뿐만 아니라 1 또는 2치환된 페닐 및 나프틸 그룹은
하이드록시, 하이드록시-C1-3-알킬 또는 C1-3-알콕시-C1-3-알킬 그룹에 의해,
시아노, 카복시, 카복시-C1-3-알킬, C1-3-알콕시카보닐, 아미노카보닐, C1-3-알킬아미노-카보닐 또는 디-(C1-3-알킬)-아미노카보닐 그룹에 의해,
니트로 그룹에 의해,
아미노, C1-3-알킬아미노, 디-(C1-3-알킬)-아미노 또는 아미노-C1-3-알킬 그룹에 의해,
C1-3-알킬카보닐아미노, N-(C1-3-알킬)-C1-3-알킬-카보닐아미노, C1-3-알킬카보닐아미노-C1-3-알킬, N-(C1-3-알킬)-C1-3-알킬카보닐아미노-C1-3-알킬, C1-3-알킬-설포닐아미노, C1-3-알킬설포닐아미노-C1-3-알킬, N-(C1-3-알킬)-C1-3-알킬설포닐아미노-C1-3-알킬 또는 아릴-C1-3-알킬설포닐아미노 그룹에 의해,
C1-3-알킬카보닐아미노, N-(C1-3-알킬)-C1-3-알킬-카보닐아미노, C1-3-알킬카보닐아미노-C1-3-알킬, N-(C1-3-알킬)-C1-3-알킬카보닐아미노-C1-3-알킬, C1-3-알킬-설포닐아미노, C1-3-알킬설포닐아미노-C1-3-알킬, N-(C1-3-알킬)-C1-3-알킬설포닐아미노-C1-3-알킬 또는 아릴-C1-3-알킬설포닐아미노 그룹에 의해,
사이클로알킬아미노, 사이클로알킬렌이미노, 사이클로알킬렌이미노카보닐, 사이클로알킬렌이미노-C1-3-알킬, 사이클로알킬렌이미노카보닐-C1-3-알킬 또는 사이클로알킬렌이미노설포닐-C1-3-알킬 그룹(여기서, 각각은 4 내지 7개의 환 원자를 갖고, 6 또는 7원의 사이클로알킬렌이미노 그룹의 4 위치에서 메틸렌 그룹은 산소 또는 황 원자, 설피닐, 설포닐, -NH 또는 -N(C1-3-알킬) 그룹으로 교체될 수 있다)에 의해,
헤테로아릴 또는 헤테로아릴-C1-3-알킬 그룹에 의해 추가로 치환될 수 있고,
R4는 C3-7-사이클로알킬 그룹(여기서, 6 또는 7원의 사이클로알킬 그룹의 4 위치에서 메틸렌 그룹은 아미노, C1-3-알킬-아미노 또는 디-(C1-3-알킬)-아미노 그룹에 의해 치환되거나 -NH 또는 -N(C1-3-알킬) 그룹으로 교체될 수 있다), 또는
삭제
동일하거나 상이할 수 있는 치환체인 플루오르, 염소, 브롬 또는 요오드 원자에 의해, C1-5-알킬, 트리플루오로메틸, 하이드록시, C1-3-알콕시, 카복시, C1-3-알콕시카보닐, 아미노, 아세틸아미노, C1-3-알킬-설포닐아미노, 아미노카보닐, C1-3-알킬-아미노카보닐, 디-(C1-3-알킬)-아미노카보닐, 아미노설포닐, C1-3-알킬-아미노설포닐, 디-(C1-3-알킬)-아미노설포닐, 니트로 또는 시아노 그룹에 의해 추가로 1 또는 2치환될 수 있는, 그룹 R6에 의해 치환된 페닐 그룹이고,
여기서 R6은 수소, 플루오르, 염소, 브롬 또는 요오드 원자,
삭제
시아노, 니트로, 아미노, C1-5-알킬, C3-7-사이클로알킬, 트리플루오로메틸, 페닐, 테트라졸릴 또는 헤테로아릴 그룹,
C1-3-알콕시 그룹, C1-3-알콕시-C1-3-알콕시, 페닐-C1-3-알콕시, 아미노-C2-3-알콕시, C1-3-알킬아미노-C2-3-알콕시, 디-(C1-3-알킬)-아미노-C2-3-알콕시, 페닐-C1-3-알킬아미노-C2-3-알콕시, N-(C1-3-알킬)-페닐-C1-3-알킬아미노-C2-3-알콕시, C5-7-사이클로알킬렌이미노-C2-3-알콕시 또는 C1-3-알킬머캅토 그룹,
카복시, C1-4-알콕시카보닐, 아미노카보닐, C1-3-알킬-아미노-카보닐, N-(C1-5-알킬)-C1-3-알킬아미노카보닐, 페닐-C1-3-알킬아미노-카보닐, N-(C1-3-알킬)-페닐-C1-3-알킬아미노-카보닐, 피페라지노카보닐 또는 N-(C1-3-알킬)-피페라지노카보닐 그룹,
C1-3-알킬아미노카보닐 또는 N-(C1-5-알킬)-C1-3-알킬아미노카보닐 그룹(여기서, 알킬 잔기는 카복시 또는 C1-3-알콕시카보닐 그룹에 의해 치환되거나, 2 또는 3 위치에서 디-(C1-3-알킬)-아미노, 피페라지노, N-(C1-3-알킬)-피페라지노 또는 4 내지 7원의 사이클로알킬렌이미노에 의해 치환된다),
C3-7-사이클로알킬-카보닐 그룹(여기서, 6 또는 7원의 사이클로알킬 잔기의 4 위치에서 메틸렌 그룹은 아미노, C1-3-알킬아미노 또는 디-(C1-3-알킬)-아미노 그룹에 의해 치환되거나, -NH 또는 -N(C1-3-알킬) 그룹으로 교체될 수 있다),
4 내지 7원의 사이클로알킬렌이미노 그룹(여기서, 이미노 그룹에 연결된 메틸렌 그룹은 카보닐 또는 설포닐 그룹으로 교체될 수 있거나, 사이클로알킬렌 잔기는 페닐 환에 융합될 수 있거나, 1 또는 2개의 수소 원자는 C1-3-알킬 그룹으로 교체될 수 있고/있거나, 각각의 경우, 6 또는 7원의 사이클로알킬렌이미노 그룹의 4 위치에서 메틸렌 그룹은 카복시, C1-3-알콕시카보닐, 아미노카보닐, C1-3-알킬아미노카보닐, 디-(C1-3-알킬)-아미노카보닐, 페닐-C1-3-알킬-아미노 또는 N-(C1-3-알킬)-페닐-C1-3-알킬아미노 그룹에 의해 치환될 수 있거나, 산소 또는 황 원자로, 설피닐, 설포닐, -NH, -N(C1-3-알킬), -N(페닐), -N(C1-3-알킬-카보닐) 또는 -N(벤조일) 그룹으로 교체될 수 있다), 또는
그룹 R7에 의해 치환된 C1-4-알킬 그룹이고,
여기서 R7은 C3-7-사이클로알킬 그룹(여기서, 6 또는 7원의 사이클로알킬 그룹의 4 위치에서 메틸렌 그룹은 아미노, C1-3-알킬아미노 또는 디-(C1-3-알킬)-아미노 그룹에 의해 치환될 수 있거나, -NH 또는 -N(C1-3-알킬) 그룹으로 교체될 수 있고, 5 내지 7원의 사이클로알킬 그룹에서 -(CH2)2 그룹은 -CO-NH 그룹으로 교체될 수 있고, -(CH2)3 그룹은 -NH-CO-NH 또는 -CO-NH-CO 그룹으로 교체될 수 있거나, -(CH2)4 그룹은 -NH-CO-NH-CO 그룹으로 교체될 수 있고, 각각의 경우 질소 원자에 결합된 수소 원자는 C1-3-알킬 그룹으로 교체될 수 있다),
삭제
아릴 또는 헤테로아릴 그룹,
하이드록시 또는 C1-3-알콕시 그룹,
아미노, C1-7-알킬아미노, 디-(C1-7-알킬)-아미노, 페닐아미노, N-페닐-C1-3-알킬-아미노, 페닐-C1-3-알킬-아미노, N-(C1-3-알킬)-페닐-C1-3-알킬아미노 또는 디-(페닐-C1-3-알킬)-아미노 그룹,
ω-하이드록시-C2-3-알킬-아미노, N-(C1-3-알킬)-ω-하이드록시-C2-3-알킬-아미노, 디-(ω-하이드록시-C2-3-알킬)-아미노, 디-(ω-(C1-3-알콕시)-C2-3-알킬)-아미노 또는 N-(디옥솔란-2-일)-C1-3-알킬-아미노 그룹,
C1-3-알킬카보닐아미노-C2-3-알킬-아미노 또는 C1-3-알킬카보닐아미노-C2-3-알킬-N-(C1-3-알킬)-아미노 그룹,
C1-3-알킬설포닐아미노, N-(C1-3-알킬)-C1-3-알킬-설포닐아미노, C1-3-알킬설포닐아미노-C2-3-알킬-아미노 또는 C1-3-알킬설포닐아미노-C2-3-알킬-N-(C1-3-알킬)-아미노 그룹,
하이드록시카보닐-C1-3-알킬아미노 또는 N-(C1-3-알킬)-하이드록시카보닐-C1-3-알킬-아미노 그룹,
구아니디노 그룹(여기서, 1 또는 2개의 수소 원자는 각각 C1-3-알킬 그룹으로 교체될 수 있다),
화학식 II의 그룹 또는
화학식 III의 그룹이거나;
R6은 카복시, C1-3-알콕시카보닐, 아미노카보닐, C1-3-알킬아미노카보닐 또는 디-(C1-3-알킬)-아미노카보닐 그룹 또는 4 내지 7원의 사이클로알킬렌이미노카보닐 그룹에 의해 치환된 C1-4-알킬 그룹, 또는
삭제
알킬 잔기에서 카복시 또는 C1-3-알콕시카보닐 그룹에 의해 추가로 치환된 N-(C1-3-알킬)-C2-4-알카노일아미노 그룹이고,
화학식 IV의 그룹,
화학식 V의 그룹 또는
화학식 VI의 그룹이고,
R6 하에 상기 언급된 그룹에서 모든 단일 결합 또는 융합된 페닐 그룹은 플루오르, 염소, 브롬 또는 요오드 원자에 의해, C1-5-알킬, 트리플루오로메틸, 하이드록시, C1-3-알콕시, 카복시, C1-3-알콕시카보닐, 아미노카보닐, C1-4-알킬아미노-카보닐, 디-(C1-4-알킬)-아미노-카보닐, 아미노설포닐, C1-3-알킬-아미노설포닐, 디-(C1-3-알킬)-아미노설포닐, C1-3-알킬-설포닐아미노, 니트로 또는 시아노 그룹에 의해 1 또는 2치환되거나(여기서 치환체는 동일하거나 상이하다), 페닐 그룹의 2개의 인접한 수소 원자는 메틸렌디옥시 그룹으로 교체될 수 있고,
R5는 수소 원자 또는 C1-3-알킬 그룹이고,
아릴 그룹은 플루오르, 염소, 브롬 또는 요오드 원자에 의해, 시아노, 트리플루오로메틸, 니트로, 카복시, 아미노카보닐, C1-3-알킬 또는 C1-3-알콕시 그룹에 의해 임의로 1 또는 2치환된 페닐 또는 나프틸 그룹이고,
헤테로아릴 그룹은 탄소 쇄에서 C1-3-알킬 그룹에 의해 임의로 치환된 모노사이클릭 5 또는 6원의 헤테로아릴 그룹이고,
여기서 6원의 헤테로아릴 그룹은 1, 2 또는 3개의 질소 원자를 함유하고,
5원의 헤테로아릴 그룹은 C1-3-알킬 또는 페닐-C1-3-알킬 그룹, 산소 또는 황 원자에 의해 임의로 치환된 이미노 그룹,
C1-3-알킬 또는 페닐-C1-3-알킬 그룹 또는 산소 또는 황 원자 및 추가로 질소 원자에 의해 임의로 치환된 이미노 그룹 또는
C1-3-알킬 또는 페닐-C1-3-알킬 그룹 및 2개의 질소 원자에 의해 임의로 치환된 이미노 그룹을 함유하고,
또한, 페닐 환은 상기 언급된 모노사이클릭 헤테로사이클릭 그룹에 2개의 인접한 탄소 원자를 통해 융합될 수 있고, 결합은 헤테로사이클릭 잔기 또는 융합된 페닐 환의 질소 원자 또는 탄소 원자를 통해 발생하고,
상기 언급된 알킬 및 알콕시 또는 화학식 I의 상기 정의된 그룹에 함유된 알킬 잔기에서 일부 또는 모든 수소 원자는 플루오르 원자로 임의로 교체될 수 있고,
상기 정의된 그룹에서 존재하는, 2개 이상의 탄소 원자를 갖는 포화된 알킬 및 알콕시 잔기는, 달리 기재되지 않는 경우, 또한 이의 측쇄 이성체, 예를 들면, 이소프로필, 3급-부틸, 이소부틸 그룹을 포함하고,
추가로 임의의 존재하는 카복시 그룹의 수소 원자 또는 질소 원자에 결합된 수소 원자, 예를 들면, 아미노, 알킬아미노 또는 이미노 그룹 또는 포화된 N-헤테로사이클, 예를 들면, 피페리디닐 그룹의 수소 원자는 생체 내에서 절단될 수 있는 그룹으로 교체될 수 있고,
이미노 또는 아미노 그룹으로부터 생체내에서 절단될 수 있는 그룹은, 예를 들면, 예를 들면, 하이드록시 그룹, 아실 그룹, 예를 들면, 벤조일 또는 피리디노일 그룹 또는 C1-16-알카노일 그룹, 예를 들면, 포밀, 아세틸, 프로피오닐, 부타노일, 펜타노일 또는 헥사노일 그룹, 알릴옥시카보닐 그룹, C1-16-알콕시카보닐 그룹, 예를 들면, 메톡시-카보닐, 에톡시카보닐, 프로폭시카보닐, 이소프로폭시카보닐, 부톡시카보닐, 3급-부톡시카보닐, 펜톡시카보닐, 헥실옥시카보닐, 옥틸옥시카보닐, 노닐옥시카보닐, 데실옥시카보닐, 언데실옥시카보닐, 도데실옥시카보닐 또는 헥사데실옥시카보닐 그룹, 페닐-C1-6-알콕시카보닐 그룹, 예를 들면, 벤질옥시카보닐, 페닐에톡시카보닐 또는 페닐프로폭시카보닐 그룹, C1-3-알킬설포닐-C2-4-알콕시카보닐, C1-3-알콕시-C2-4-알콕시-C2-4-알콕시카보닐 또는 ReCO-O-(RfCRg)-O-CO 그룹이고,
Re는 C1-8-알킬, C5-7-사이클로알킬, 페닐 또는 페닐-C1-3-알킬 그룹이고,
Rf는 수소 원자, C1-3-알킬, C5-7-사이클로알킬 또는 페닐 그룹이고,
Rg는 수소 원자, C1-3-알킬 또는 ReCO-O-(RfCRg)-O 그룹이고, Re 내지 Rg 는 상기 정의된 바와 같고,
추가로 아미노 그룹은 프탈이미도 그룹, 상기 언급된 에스테르 그룹은 또한 생체내에서 카복시 그룹으로 전환될 수 있는 그룹으로서 사용될 수 있다.
위의 화학식 II에서,
R8은 수소 원자 또는 C1-3-알킬 그룹이고,
n은 수 0, 1, 2 또는 3 중 하나이고,
R9는 아미노, C1-4-알킬아미노, 디-(C1-4-알킬)-아미노, 페닐아미노, N-(C1-4-알킬)-페닐아미노, 벤질아미노, N-(C1-4-알킬)-벤질아미노 또는 C1-4-알콕시 그룹, 4 내지 7원의 사이클로알킬렌이미노 그룹이고, 각각의 경우 6 또는 7원의 사이클로알킬렌이미노 그룹의 4 위치에서 메틸렌 그룹은 산소 또는 황 원자로, 설피닐, 설포닐, -NH, -N(C1-3-알킬), -N(페닐), -N(C1-3-알킬-카보닐) 또는 -N(벤조일) 그룹으로 교체될 수 있거나, n이 수 1, 2 또는 3 중 하나인 경우, 이는 또한 수소 원자를 의미한다.
위의 화학식 III에서,
R10은 수소 원자, C1-3-알킬 그룹, C1-3-알킬카보닐, 아릴카보닐, 페닐-C1-3-알 킬-카보닐, C1-3-알킬설포닐, 아릴설포닐 또는 페닐-C1-3-알킬설포닐 그룹이고,
m은 수 1, 2, 3 또는 4 중 하나이고,
o는 수 1이거나, m이 수 2, 3 또는 4 중 하나인 경우, o는 또한 수 0일 수 있고,
R11은 아미노, C1-4-알킬아미노, 디-(C1-4-알킬)-아미노, 페닐아미노, N-(C1-4-알킬)-페닐아미노, 벤질아미노, N-(C1-4-알킬)-벤질아미노, C1-4-알콕시 또는 C1-3-알콕시-C1-3-알콕시 그룹, 1 위치에서 C1-3-알킬 그룹 또는 4 내지 7원의 사이클로알킬렌이미노 그룹에 의해 임의로 치환된 디-(C1-4-알킬)-아미노-C1-3-알킬아미노 그룹(여기서, 사이클로알킬렌 잔기는 페닐 환에 융합될 수 있거나, 각각의 경우 6 또는 7원의 사이클로알킬렌이미노 그룹의 4 위치에서 메틸렌 그룹은 산소 또는 황 원자로, 설피닐, 설포닐, -NH, -N(C1-3-알킬), -N(페닐), -N(C1-3-알킬-카보닐) 또는 -N(벤조일) 그룹으로 교체될 수 있다),
C4-7-사이클로알킬아미노, C4-7-사이클로알킬-C1-3-알킬아미노 또는 C4-7-사이클로알케닐아미노 그룹(여기서, 환의 1 위치는 이중 결합에 포함되지 않고, 상기 언급된 그룹은 각각 추가로 아미노-질소 원자에서 C5-7-사이클로알킬, C2-4-알케닐 또는 C1-4-알킬 그룹에 의해 치환될 수 있다), 또는
4 내지 7원의 사이클로알킬렌이미노 그룹이고,
여기서, 사이클로알킬렌 잔기는 페닐 그룹, 또는 플루오르, 염소, 브롬 또는 요오드 원자에 의해, 니트로, C1-3-알킬, C1-3-알콕시 또는 아미노 그룹에 의해 임의로 치환된 옥사졸로, 이미다졸로, 티아졸로, 피리디노, 피라지노 또는 피리미디노 그룹에 융합될 수 있고/있거나,
1 또는 2개의 수소 원자는 각각 C1-3-알킬, C5-7-사이클로알킬 또는 페닐 그룹으로 교체될 수 있고/있거나,
5원의 사이클로알킬렌이미노 그룹의 3 위치에서 메틸렌 그룹은 하이드록시, 하이드록시-C1-3-알킬, C1-3-알콕시 또는 C1-3-알콕시-C1-3-알킬 그룹에 의해 치환될 수 있고,
6 또는 7원의 사이클로알킬렌이미노 그룹의 3 또는 4 위치에서 메틸렌 그룹은 각각 하이드록시, 하이드록시-C1-3-알킬, C1-3-알콕시, C1-3-알콕시-C1-3-알킬, 카복시, C1-4-알콕시카보닐, 아미노-카보닐, C1-3-알킬아미노카보닐, 디-(C1-3-알킬)-아미노카보닐, 페닐-C1-3-알킬아미노 또는 N-(C1-3-알킬)-페닐-C1-3-알킬-아미노 그룹에 의해 치환될 수 있거나,
산소 또는 황 원자로, 설피닐, 설포닐, -NH, -N(C1-3-알킬-), -N(페닐), -N(페닐-C1-3-알킬-), -N(C1-3-알킬-카보닐-), -N(C1-4-알킬-하이드록시-카보닐-), -N(C1-4-알콕시-카보닐-), -N(벤조일-) 또는 -N(페닐-C1-3-알킬-카보닐-) 그룹으로 교체될 수 있고,
사이클로알킬렌이미노 그룹의 이미노-질소 원자에 연결된 메틸렌 그룹은 카 보닐 또는 설포닐 그룹으로 교체될 수 있거나, 5 내지 7원의 모노사이클릭 사이클로알킬렌이미노 그룹 또는 페닐 그룹에 융합된 사이클로알킬렌이미노 그룹에서 이미노-질소 원자에 연결된 2개의 메틸렌 그룹은 각각 카보닐 그룹으로 교체될 수 있다.
위의 화학식 IV에서,
R12는 수소 원자, C1-6-알킬 또는 C3-7-사이클로알킬 그룹, 또는 페닐, 헤테로아릴, 트리플루오로메틸, 하이드록시, C1-3-알콕시, 아미노카보닐, C1-4-알킬아미노-카보닐, 디-(C1-4-알킬)-아미노-카보닐, C1-3-알킬-카보닐, C1-3-알킬-설포닐-아미노, N-(C1-3-알킬)-C1-3-알킬-설포닐아미노, C1-3-알킬-아미노설포닐 또는 디-(C1-3-알킬)-아미노설포닐 그룹에 의해 말단 치환된 C1-3-알킬 그룹이고,
p는 수 0, 1, 2 또는 3 이고,
R13은 상기 언급된 그룹 R7과 같거나, p가 수 1, 2 또는 3 중 하나인 경우, 수소 원자이다.
위의 화학식 V에서,
R14는 수소 원자, C1-4-알킬 그룹, C1-3-알킬카보닐, 아릴카보닐, 페닐-C1-3-알킬카보닐, 헤테로아릴카보닐, 헤테로아릴-C1-3-알킬카보닐, C1-4-알킬설포닐, 아릴설포닐, 페닐-C1-3-알킬설포닐, 헤테로아릴설포닐 또는 헤테로아릴-C1-3-알킬-설포닐 그룹이고,
q는 수 1, 2, 3 또는 4 중의 하나이고,
r은 수 1이거나, q가 수 2, 3 또는 4 중의 하나인 경우, 수 0일 수 있고,
R15는 상기 언급된 그룹 R7의 의미와 같다.
위의 화학식 VI에서,
R16은 수소 원자 또는, 시아노, 트리플루오로메틸-카보닐아미노 또는 N-(C1-3-알킬)-트리플루오로메틸-카보닐-아미노 그룹에 의해 임의로 말단 치환된 C1-4-알킬 그룹이고,
R17은 C1-3-알킬 그룹,
삭제
디-(C1-3-알킬)-아미노-C1-3-알킬-카보닐 또는 디-(C1-3-알킬)-아미노-C1-3-알킬-설포닐 그룹 및 디-(C1-3-알킬)-아미노카보닐-C1-3-알킬 그룹에 의해 치환된 아미노 그룹, 또는
N-(C1-3-알킬)-C1-5-알킬설포닐아미노 또는 N-(C1-3-알킬)-페닐설포닐아미노 그룹(여기서, 알킬 잔기는 시아노 또는 카복시 그룹에 의해 추가로 치환된다)이다.
특별히 언급되는 화학식 I의 화합물의 하위 그룹은
X, R1 및 R3 내지 R5가 상기 정의된 바와 같고,
R2가 직쇄 또는 측쇄 C1-6-알콕시-카보닐 그룹, C4-7-사이클로알콕시카보닐 또는 아릴옥시카보닐 그룹,
알킬 잔기에서 페닐, 헤테로아릴, 카복시, C1-3-알콕시카보닐, 아미노카보닐, C1-3-알킬아미노카보닐 또는 디-(C1-3-알킬)-아미노카보닐 그룹에 의해 말단 치환된 직쇄 또는 측쇄 C1-6-알콕시-카보닐 그룹, 또는
알킬 잔기에서 염소 원자 또는 하이드록시, C1-3-알콕시, 아미노, C1-3-알킬아미노 또는 디-(C1-3-알킬)-아미노 그룹에 의해 말단 치환된 직쇄 또는 측쇄 C2-6-알콕시-카보닐 그룹인 화학식 I의 화합물, 및 이의 토오토머, 디아스테레오머, 에난티오머, 혼합물 및 염을 포함한다.
특별히 언급되는 화학식 I의 화합물의 제2 하위 그룹은
X, R1 및 R3 내지 R5가 상기 정의된 바와 같고,
R2가 아미노카보닐 또는 메틸아미노카보닐 그룹, 에틸 그룹의 2 위치가 하이 드록시 또는 C1-3-알콕시 그룹 또는 디-(C1-2-알킬)-아미노카보닐 그룹에 의해 임의로 치환된 에틸아미노카보닐 그룹인 화학식 I의 화합물, 및 이의 토오토머, 디아스테레오머, 에난티오머, 혼합물 및 염을 포함한다.
특별히 언급되는 화학식 I의 화합물의 제3 하위 그룹은
X, R1 내지 R3 및 R5가 상기 정의된 바와 같고,
R4가 R7-(C1-4-알킬)-페닐 그룹이고,
R7이 아미노, C1-7-알킬아미노, 디-(C1-7-알킬)-아미노, 페닐아미노, N-페닐-C1-3-알킬-아미노, 페닐-C1-3-알킬-아미노, N-(C1-3-알킬)-페닐-C1-3-알킬아미노 또는 디-(페닐-C1-3-알킬)-아미노 그룹, 또는
화학식 IV의 그룹에 의해 치환된 페닐 그룹인 화학식 I의 화합물, 및 이의 토오토머, 디아스테레오머, 에난티오머, 혼합물 및 염을 포함한다.
화학식 IV
-N(R12)-CO-(CH2)p-R13
여기서, R12, p 및 R13는 상기 정의된 바와 같다.
바람직한 화학식 I의 화합물은
R1 및 R3이 상기 정의된 바와 같고,
X가 산소 원자이고,
R2가 카복시 그룹, 직쇄 또는 측쇄 C1-6-알콕시-카보닐 그룹, C5-7-사이클로알콕시카보닐 또는 펜옥시카보닐 그룹,
알킬 잔기에서 페닐, 헤테로아릴, 카복시, C1-3-알콕시카보닐, 아미노카보닐, C1-3-알킬아미노카보닐 또는 디-(C1-3-알킬)-아미노카보닐 그룹에 의해 말단 치환된 직쇄 또는 측쇄 C1-3-알콕시-카보닐 그룹,
알킬 잔기에서 염소 원자에 의해, 하이드록시, C1-3-알콕시, 아미노, C1-3-알킬아미노 또는 디-(C1-3-알킬)-아미노 그룹에 의해 말단 치환된 직쇄 또는 측쇄 C2-3-알콕시-카보닐 그룹, 또는
아미노카보닐 또는 메틸아미노카보닐 그룹, 에틸 그룹의 2 위치에서 하이드록시 또는 C1-3-알콕시 그룹 또는 디-(C1-2-알킬)-아미노카보닐 그룹에 의해 임의로 치환된 에틸아미노카보닐 그룹이고,
R4가 C3-7-사이클로알킬 그룹(여기서, 6 또는 7원의 사이클로알킬 그룹의 4 위치에서 메틸렌 그룹은 아미노, C1-3-알킬아미노 또는 디-(C1-3-알킬)-아미노 그룹으로 치환될 수 있거나, -NH 또는 -N(C1-3-알킬) 그룹으로 교체될 수 있다) 또는
삭제
플루오르, 염소 또는 브롬 원자에 의해, C1-3-알킬, 트리플루오로메틸, 하이드록시, C1-3-알콕시, 카복시, C1-3-알콕시카보닐, 아미노, 아세틸아미노, 아미노카보닐, C1-3-알킬아미노카보닐, 디-(C1-3-알킬)-아미노카보닐, 니트로 또는 시아노 그룹에 의해 추가로 1 또는 2치환될 수 있고, 치환체는 동일하거나 상이할 수 있는, 그룹 R6에 의해 치환된 페닐 그룹이고,
R6이 수소, 플루오르, 염소, 브롬 또는 요오드 원자,
삭제
시아노, 니트로, 아미노, C1-5-알킬, C3-7-사이클로알킬, 트리플루오로메틸, 페닐, 테트라졸릴 또는 헤테로아릴 그룹,
C1-3-알콕시 그룹, 아미노-C2-3-알콕시, C1-3-알킬아미노-C2-3-알콕시, 디-(C1-3-알킬)-아미노-C2-3-알콕시, 페닐-C1-3-알킬아미노-C2-3-알콕시, N-(C1-3-알킬)-페닐-C1-3-알킬아미노-C2-3-알콕시, 피롤리디노-C2-3-알콕시, 피페리디노-C2-3-알콕시 또는 C1-3-알킬머캅토 그룹,
카복시, C1-4-알콕시카보닐, 아미노카보닐, C1-3-알킬-아미노-카보닐, 페닐-C1-3-알킬아미노-카보닐 또는 N-(C1-3-알킬)-페닐-C1-3-알킬아미노-카보닐 그룹,
C3-7-사이클로알킬-카보닐 그룹(여기서, 6 또는 7원의 사이클로알킬 잔기의 4 위치에서 메틸렌 그룹은 -NH 또는 -N(C1-3-알킬) 그룹으로 교체될 수 있다),
4 내지 7원의 사이클로알킬렌이미노 그룹(여기서, 이미노 그룹에 연결된 메틸렌 그룹은 카보닐 또는 설포닐 그룹으로 교체될 수 있고, 1 또는 2개의 수소 원자는 각각 C1-3-알킬 그룹으로 교체될 수 있고/있거나, 각각의 경우, 6 또는 7원의 사이클로알킬렌이미노 그룹의 4 위치에서 메틸렌 그룹은 카복시, C1-3-알콕시카보닐, 아미노카보닐, C1-3-알킬아미노카보닐, 디-(C1-3-알킬)-아미노카보닐, 페닐-C1-3-알킬-아미노 또는 N-(C1-3-알킬)-페닐-C1-3-알킬아미노 그룹으로 치환될 수 있거나, 산소 또는 황 원자로, 설피닐, 설포닐, -NH 또는 -N(C1-3-알킬) 그룹으로 교체될 수 있다) 또는
그룹 R7에 의해 말단 치환된 C1-4-알킬 그룹이고,
R7이 C5-7-사이클로알킬 그룹(여기서, 6 또는 7원의 사이클로알킬 그룹의 4 위치에서 메틸렌 그룹은 -NH 또는 -N(C1-3-알킬) 그룹으로 교체되거나, 5 내지 7원의 사이클로알킬 그룹에서, -(CH2)2 그룹은 -CO-NH 그룹으로 교체될 수 있고, -(CH2)3 그룹은 -NH-CO-NH-으로 교체될 수 있거나, -(CH2)4 그룹은 -NH-CO-NH-CO 그룹으로 교체될 수 있고, 각각의 경우, 질소 원자에 결합한 수소 원자는 C1-3-알킬 그룹으로 교체될 수 있다),
페닐 또는 헤테로아릴 그룹,
하이드록시 또는 C1-3-알콕시 그룹,
아미노, C1-6-알킬아미노, 디-(C1-6-알킬)-아미노, 페닐아미노, N-페닐-C1-3-알킬-아미노, 페닐-C1-3-알킬아미노, N-(C1-3-알킬)-페닐-C1-3-알킬아미노 또는 디-(페닐-C1-3-알킬)-아미노 그룹,
ω-하이드록시-C2-3-알킬-아미노, N-(C1-3-알킬)-ω-하이드록시-C2-3-알킬-아미노, 디-(ω-하이드록시-C2-3-알킬)-아미노, 디-(ω-(C1-3-알콕시)-C2-3-알킬)-아미노 또는 N-(디옥솔란-2-일)-C1-3-알킬-아미노 그룹,
C1-3-알킬카보닐아미노-C2-3-알킬-아미노 또는 C1-3-알킬카보닐아미노-C2-3-알킬-N-(C1-3-알킬)-아미노 그룹,
C1-3-알킬설포닐아미노, N-(C1-3-알킬)-C1-3-알킬설포닐아미노, C1-3-알킬설포닐아미노-C2-3-알킬-아미노 또는 C1-3-알킬설포닐아미노-C2-3-알킬-N-(C1-3-알킬)-아미노 그룹,
하이드록시카보닐-C1-3-알킬아미노 또는 N-(C1-3-알킬)-하이드록시카보닐-C1-3-알킬-아미노 그룹,
수소 원자가 C1-3-알킬 그룹으로 교체될 수 있는 구아니디노 그룹,
화학식 II의 그룹 또는
화학식 III의 그룹이거나;
R6이 카복시, C1-3-알콕시카보닐, 아미노카보닐, C1-3-알킬아미노-카보닐 또는 디-(C1-3-알킬)-아미노카보닐 그룹 또는 4 내지 7원의 사이클로알킬렌이미노카보닐 그룹에 의해 말단 치환된 C1-4-알킬 그룹,
화학식 IV의 그룹,
화학식 V의 그룹 또는
화학식 VI의 그룹이고,
여기서, R6하에 언급된 그룹에 함유된 모든 단일 결합 또는 융합된 페닐 그룹은 플루오르, 염소 또는 브롬 원자에 의해, C1-3-알킬, 트리플루오로메틸, 하이드록시, C1-3-알콕시, 카복시, C1-3-알콕시카보닐, 아미노카보닐, C1-3-알킬-아미노카보닐, 아미노설포닐, C1-3-알킬-아미노설포닐, 니트로 또는 시아노 그룹에 의해 1 또는 2치환될 수 있거나(여기서 치환체는 동일하거나 상이할 수 있다), 페닐 그룹의 2개의 인접한 수소 원자는 메틸렌디옥시 그룹으로 교체될 수 있고,
여기서, R6하에 언급된 그룹에 함유된 모든 단일 결합 또는 융합된 페닐 그룹은 플루오르, 염소 또는 브롬 원자에 의해, C1-3-알킬, 트리플루오로메틸, 하이드록시, C1-3-알콕시, 카복시, C1-3-알콕시카보닐, 아미노카보닐, C1-3-알킬-아미노카보닐, 아미노설포닐, C1-3-알킬-아미노설포닐, 니트로 또는 시아노 그룹에 의해 1 또는 2치환될 수 있거나(여기서 치환체는 동일하거나 상이할 수 있다), 페닐 그룹의 2개의 인접한 수소 원자는 메틸렌디옥시 그룹으로 교체될 수 있고,
R5는 수소 원자 또는 C1-3-알킬 그룹이고,
상기 언급된 헤테로아릴 그룹은 탄소 쇄에서 C1-3-알킬 그룹에 의해 임의로 치환될 수 있는 피리디닐, 피라지닐, 피리미디닐, 피리다지닐, 피롤릴, 푸릴, 티에닐, 옥사졸릴, 티아졸릴, 피라졸릴, 이미다졸릴 또는 트리아졸릴 그룹이고, 하나 이상의 이미노 그룹을 함유하는 5원의 헤테로아릴 그룹은 탄소 또는 질소 원자를 통해 결합되고,
상기 언급된 그룹에서 질소 원자에 결합한 수소 원자는 생체내에서 절단될 수 있는 그룹, 특히 아세틸 또는 3급-부톡시카보닐 그룹으로 교체될 수 있고,
상기 언급된 그룹에서 함유된 카복시 그룹은 생체내에서 절단될 수 있는 그룹에 의해 각각 치환될 수 있고, 예를 들면, 3급-부톡시카보닐 그룹의 형태로 발생할 수 있고,
상기 언급된 알킬 및 알콕시 그룹 또는 화학식 I의 상기 정의된 그룹에 함유 된 알킬 잔기에서 일부 또는 모든 수소 원자는 임의로 플루오르 원자로 교체될 수 있고,
2개 이상의 탄소 원자를 함유하는, 상기 정의된 그룹에 함유된 포화된 알킬 및 알콕시 잔기는, 달리 기재되지 않는 경우, 직쇄 또는 측쇄일 수 있는, 화학식 I의 화합물, 및 이의 토오토머, 디아스테레오머, 에난티오머, 혼합물 및 염을 포함한다.
화학식 II
-N(R8)-CO-(CH2)n-R9
위의 화학식 II에서,
R8는 수소 원자 또는 C1-3-알킬 그룹이고,
n은 수 0, 1, 2 또는 3 중의 하나이고,
R9는 아미노, C1-3-알킬아미노, 디-(C1-3-알킬)-아미노, 페닐아미노, 벤질아미노 또는 C1-4-알콕시 그룹, 5 내지 7원의 사이클로알킬렌이미노 그룹이고, 여기서 피페리디노 그룹의 4 위치에서 메틸렌 그룹은 산소 또는 황 원자로, -NH, -N(C1-3-알킬), -N(페닐), -N(C1-3-알킬-카보닐) 또는 -N(벤조일) 그룹으로 치환되거나, n이 수 1, 2 또는 3 중의 하나인 경우, 수소 원자일 수 있다.
화학식 III
-N(R10)-(CH2)m-(CO)o-R11
위의 화학식 III에서,
R10은 수소 원자, C1-3-알킬 그룹, C1-3-알킬카보닐 또는 C1-3-알킬설포닐 그룹이고,
m은 수 1, 2 또는 3 중의 하나이고,
o는 수 1이거나, m이 수 2 또는 3 중의 하나인 경우, o는 또한 수 0일 수 있고,
R11은 아미노, C1-3-알킬아미노, 디-(C1-3-알킬)-아미노, C1-4-알콕시 또는 C1-3-알콕시-C1-3-알콕시 그룹 또는 5 내지 7원의 사이클로알킬렌이미노 그룹(여기서 피페리디노 그룹의 4 위치에서 메틸렌 그룹은 산소 또는 황 원자로, -NH, -N(C1-3-알킬), -N(페닐), -N(C1-3-알킬-카보닐) 또는 -N(벤조일) 그룹으로 교체될 수 있다)
C4-7-사이클로알킬아미노 또는 C4-7-사이클로알케닐아미노 그룹(여기서, 환의 1 위치는 이중 결합에 포함되지 않는다), 또는
4 내지 7원의 사이클로알킬렌이미노 그룹(여기서, 사이클로알킬렌 잔기는 페닐 그룹에 융합될 수 있거나, 1 또는 2개의 수소 원자는 C1-3-알킬 그룹에 의해 치환될 수 있고/있거나, 피롤리디노 그룹의 3 위치에서 메틸렌 그룹은 하이드록시 또는 C1-3-알콕시 그룹에 의해 치환될 수 있고, 각각의 경우, 6 또는 7원의 사이클로알킬렌이미노 그룹의 4 위치에서 메틸렌 그룹은 하이드록시, 하이드록시-C1-3-알킬, C1-3-알콕시, 카복시, C1-3-알콕시카보닐, 아미노카보닐, C1-3-알킬아미노카보닐, 디-(C1-3-알킬)-아미노카보닐, 페닐-C1-3-알킬아미노 또는 N-(C1-3-알킬)-페닐-C1-3-알킬아미노 그룹에 의해 치환될 수 있거나, 산소 또는 황 원자로, 설피닐, 설포닐, -NH, -N(C1-3-알킬), -N(페닐), -N(페닐-C1-3-알킬), -N(C1-3-알킬-카보닐), -N(C1-4-알콕시-카보닐), -N(벤조일) 또는 -N(페닐-C1-3-알킬-카보닐) 그룹으로 교체될 수 있고, 사이클로알킬렌이미노 그룹의 이미노-질소 원자에 연결된 메틸렌 그룹은 카보닐 또는 설포닐 그룹으로 교체될 수 있거나, 5 또는 6원의 모노사이클릭 사이클로알킬렌이미노 그룹 또는 페닐 그룹에 융합된 사이클로알킬렌이미노 그룹에서, 각각 이미노-질소 원자에 연결된 2개의 메틸렌 그룹은 카보닐 그룹으로 교체될 수 있다)이다.
화학식 IV
-N(R12)-CO-(CH2)p-R13
위의 화학식 IV에서,
R12는 수소 원자, C1-3-알킬, C5-7-사이클로알킬, 페닐-C1-3-알킬 또는 헤테로아릴-C1-3-알킬 그룹이고,
p는 수 0, 1, 2 또는 3 중의 하나이고,
R13은 상기 언급된 그룹 R7의 정의와 같거나, p가 수 1, 2 또는 3 중의 하나인 경우, 수소 원자일 수 있다.
화학식 V
-N(R14)-(CH2)q-(CO)r-R15 (V),
위의 화학식 V에서,
R14는 수소 원자, C1-4-알킬 그룹, C1-3-알킬카보닐, 페닐카보닐, 페닐-C1-3-알킬-카보닐, 헤테로아릴카보닐, 헤테로아릴-C1-3-알킬카보닐, C1-4-알킬설포닐, 페닐설포닐, 페닐-C1-3-알킬-설포닐- 헤테로아릴설포닐 또는 헤테로아릴-C1-3-알킬-설포닐 그룹이고,
q는 수 1, 2, 3 또는 4 중의 하나이고,
r는 수 1이거나, q가 수 2, 3 또는 4 중의 하나인 경우, 수 0일 수 있고,
R15는 상기 언급된 그룹 R7이다.
화학식 VI
-N(R16)-SO2-R17
위의 화학식 VI에서,
R16은 수소 원자, 또는 시아노, 트리플루오로메틸-카보닐아미노 또는 N-(C1-3-알킬)-트리플루오로메틸-카보닐-아미노 그룹에 의해 임의로 말단 치환된 C1-4-알킬 그룹이고,
R17은 C1-3-알킬 그룹, 또는
디-(C1-3-알킬)-아미노-C1-3-알킬-카보닐 또는 디-(C1-3-알킬)-아미노-C1-3-알킬-설포닐 그룹 및 디-(C1-3-알킬)-아미노카보닐-C1-3-알킬 그룹에 의해 치환된 아미노 그룹이다.
특별히 언급될 만한 화학식 I의 바람직한 화합물의 하위 그룹은
X, R1 및 R3 내지 R5가 상기 정의된 바와 같고,
R2가 직쇄 또는 측쇄 C1-6-알콕시-카보닐 그룹, C5-7-사이클로알콕시카보닐 또는 펜옥시카보닐 그룹,
알킬 잔기에서 페닐- 카복시, C1-3-알콕시카보닐, 아미노카보닐, C1-3-알킬아미노카보닐 또는 디-(C1-3-알킬)-아미노카보닐 그룹에 의해 말단 치환된 직쇄 또는 측쇄 C1-3-알콕시-카보닐 그룹 또는
알킬 잔기에서 하이드록시, C1-3-알콕시, 아미노, C1-3-알킬아미노 또는 디-(C1-3-알킬)-아미노 그룹에 의해 말단 치환된 직쇄 또는 측쇄 C2-3-알콕시-카보닐 그룹인 화학식 I의 화합물, 및 이의 토오토머, 디아스테레오머, 에난티오머, 혼합물 및 염을 포함한다.
특별히 언급될 만한 바람직한 화학식 I의 화합물의 제2 하위 그룹은
X, R1 및 R3 내지 R5이 상기 정의된 바와 같고,
R2가 아미노카보닐 또는 메틸아미노카보닐 그룹, 에틸 그룹의 2 위치에서 하이드록시 또는 C1-3-알콕시 그룹 또는 디-(C1-2-알킬)-아미노카보닐 그룹에 의해 임의로 치환된 에틸아미노카보닐 그룹인 화학식 I의 화합물, 및 이의 토오토머, 디아스테레오머, 에난티오머, 혼합물 및 염을 포함한다.
특별히 언급될 만한 바람직한 화학식 I의 화합물의 제3 하위 그룹은
X, R1 내지 R3 및 R5이 상기 정의된 바와 같고,
R4가 R7-(n-C1-4-알킬)-페닐 그룹이고,
R7이 아미노, C1-6-알킬아미노, 디-(C1-6-알킬)-아미노, 페닐아미노, N-페닐-C1-3-알킬-아미노, 페닐-C1-3-알킬-아미노, N-(C1-3-알킬)-페닐-C1-3-알킬아미노 또는 디-(페닐-C1-3-알킬)-아미노 그룹 또는
화학식 IV의 그룹에 의해 치환된 페닐 그룹인 화학식 I의 화합물, 및 이의 토오토머, 디아스테레오머, 에난티오머, 혼합물 및 염을 포함한다.
화학식 IV
-N(R12)-CO-(CH2)p-R13
위의 화학식 IV에서,
R12, p 및 R13는 상기 정의된 바와 같다.
특히 바람직한 화학식 I의 화합물은
X가 산소 원자이고,
R1이 수소 원자이고,
R2가 카복시 그룹, 직쇄 또는 측쇄 C1-4-알콕시카보닐 그룹 또는 펜옥시카보닐 그룹,
알킬 잔기에서 페닐, 카복시, C1-3-알콕시카보닐, 아미노카보닐, C1-3-알킬아미노카보닐 또는 디-(C1-3-알킬)-아미노카보닐 그룹에 의해 말단 치환된 직쇄 또는 측쇄 C1-3-알콕시-카보닐 그룹,
알킬 잔기에서 하이드록시, C1-3-알콕시, 아미노, C1-3-알킬아미노 또는 디-(C1-3-알킬)-아미노 그룹에 의해 말단 치환된 직쇄 또는 측쇄 C2-3-알콕시-카보닐 그룹 또는
아미노카보닐 또는 메틸아미노카보닐 그룹, 에틸 그룹의 2 위치에서 하이드록시 또는 C1-3-알콕시 그룹 또는 디-(C1-2-알킬)-아미노카보닐 그룹에 의해 임의로 치환된 에틸아미노카보닐 그룹이고,
R3이 플루오르, 염소 또는 브롬 원자에 의해, 트리플루오로메틸, C1-3-알킬, 하이드록시 또는 C1-3-알콕시 그룹에 의해 치환될 수 있는 C1-4-알킬 그룹 또는 페닐 그룹이고,
R4가 C5-6-사이클로알킬 그룹(여기서, 사이클로헥실 그룹의 4 위치에서 메틸렌 그룹은 아미노, C1-3-알킬아미노 또는 디-(C1-3-알킬)-아미노 그룹에 의해 치환될 수 있거나, -NH 또는 -N(C1-3-알킬 그룹으로 교체될 수 있다),
페닐 그룹, C1-3-알킬, C1-3-알콕시 또는 니트로 그룹으로 2치환된 페닐 그룹(여기서, 치환체는 동일하거나 상이할 수 있다) 또는
플루오르, 염소 또는 브롬 원자에 의해 또는 아미노 또는 니트로 그룹에 의해 추가로 치환될 수 있는, 그룹 R6에 의해 치환된 페닐 그룹이고,
R6이 플루오르, 염소 또는 브롬 원자,
C1-3-알킬, C1-3-알콕시, 니트로, 아미노 또는 C5-6-사이클로알킬 그룹,
탄소 원자를 통해 결합된 피롤릴, 피라졸릴, 이미다졸릴, 트리아졸릴 또는 테트라졸릴 그룹(여기서, 탄소 쇄에서 상기 언급된 헤테로방향족 그룹은 C1-3-알킬 그룹에 의해 치환될 수 있거나, 질소 원자에 결합된 수소 원자는 C1-3-알킬 또는 페닐-C1-3-알킬 그룹으로 교체될 수 있다),
카복시, C1-4-알콕시카보닐, 페닐-C1-3-알킬-아미노-카보닐 또는 C5-7-사이클로 알킬-카보닐 그룹,
5 또는 6원의 사이클로알킬렌이미노 그룹(여기서, 피페리디노 그룹의 4 위치에서 메틸렌 그룹은 산소 또는 황 원자로, -NH 또는 -N(C1-3-알킬) 그룹으로 교체될 수 있다) 또는
그룹 R7에 의해 말단 치환된 비측쇄 C1-3-알킬 그룹이고,
R7이 C5-7-사이클로알킬 그룹(여기서, 5 또는 6원의 사이클로알킬 그룹에서 -(CH2)2 그룹은 -CO-NH 그룹으로 교체될 수 있거나, -(CH2)3 그룹은 -NH-CO-NH-로 교체될 수 있거나, -(CH2)4 그룹은 -NH-CO-NH-CO 그룹으로 교체될 수 있고, 각각의 질소 원자에 결합된 수소 원자는 C1-3-알킬 그룹으로 교체될 수 있다),
삭제
탄소 또는 질소 원자를 통해 연결된 페닐 또는 피리디닐 그룹 또는 피롤릴, 피라졸릴, 이미다졸릴 또는 트리아졸릴 그룹(여기서, 탄소 쇄에서 상기 언급된 헤테로방향족 그룹은 C1-3-알킬 그룹으로 치환될 수 있거나, 질소 원자에 결합된 수소 원자는 C1-3-알킬 그룹으로 교체될 수 있다),
하이드록시 또는 C1-3-알콕시 그룹,
아미노, C1-6-알킬아미노, 디-(C1-6-알킬)-아미노, 페닐아미노, N-페닐-C1-3-알킬아미노, 페닐-C1-3-알킬아미노 또는 N-(C1-3-알킬)-페닐-C1-3-알킬아미노 그룹,
ω-하이드록시-C2-3-알킬-아미노, N-(C1-3-알킬)-ω-하이드록시-C2-3-알킬아미노, 디-(ω-하이드록시-C2-3-알킬)-아미노 또는 디-(ω-(C1-3-알콕시)-C2-3-알킬)-아미노 그룹,
C1-3-알킬카보닐아미노-C2-3-알킬-아미노 또는 C1-3-알킬카보닐아미노-C2-3-알킬-N-(C1-3-알킬)-아미노 그룹,
C1-3-알킬설포닐아미노, N-(C1-3-알킬)-C1-3-알킬설포닐아미노, C1-3-알킬설포닐아미노-C2-3-알킬아미노 또는 C1-3-알킬설포닐아미노-C2-3-알킬-N-(C1-3-알킬)-아미노 그룹,
하이드록시카보닐-C1-3-알킬아미노 또는 N-(C1-3-알킬)-하이드록시카보닐-C1-3-알킬-아미노 그룹,
구아니디노 그룹(여기서, 수소 원자는 C1-3-알킬 그룹으로 교체될 수 있다),
화학식 II의 그룹 또는
화학식 III의 그룹이거나,
R6이 카복시 또는 C1-3-알콕시-카보닐 그룹에 의해 말단 치환된 직쇄 C1-3-알킬 그룹,
화학식 IV의 그룹,
화학식 V의 그룹 또는
화학식 VI의 그룹이고,
R6 하에 언급된 그룹에서 모든 단일 결합된 또는 융합된 페닐 그룹은 플루오르, 염소 또는 브롬 원자에 의해, 메틸, 트리플루오로메틸, 메톡시, 니트로 또는 시아노 그룹에 의해 치환될 수 있고,
R5이 수소 원자이고,
상기 언급된 그룹에서 질소 원자에 결합된 수소 원자는 아세틸 또는 3급-부톡시카보닐 그룹으로 교체될 수 있고,
상기 언급된 그룹에 함유된 카복시 그룹은 또한 3급-부톡시카보닐 전구체 그룹의 형태로 존재할 수 있고,
2개 이상의 탄소 원자를 함유하는 상기 언급된 그룹에 함유된 포화된 알킬 및 알콕시 잔기는, 달리 언급되지 않는 경우, 직쇄 또는 측쇄일 수 있는, 화학식 I의 화합물, 및 이의 토오토머, 디아스테레오머, 에난티오머, 혼합물 및 염을 포함한다.
화학식 II
화학식 II
-N(R8)-CO-(CH2)n-R9
위의 화학식 II에서,
R8은 수소 원자 또는 C1-3-알킬 그룹이고,
n은 수 0, 1, 2 또는 3 중의 하나이고,
R9는 아미노, C1-3-알킬아미노, 디-(C1-3-알킬)-아미노 또는 C1-4-알콕시 그룹, 5 또는 6원의 사이클로알킬렌이미노 그룹(여기서, 피페리디노 그룹의 4 위치에서 메틸렌 그룹은 -NH, -N(C1-3-알킬) 또는 -N(C1-3-알킬-카보닐) 그룹으로 교체될 수 있거나, n은 수 1, 2 또는 3 중의 하나인 경우, R9는 또한 수소 원자일 수 있다.
화학식 III
-N(R10)-(CH2)m-(CO)o-R11
위의 화학식 III에서,
R10은 수소 원자 또는 C1-3-알킬 그룹이고,
m은 수 1, 2 또는 3 중의 하나이고,
o는 수 1이거나, m이 수 2 또는 3 중의 하나인 경우, o는 또한 0일 수 있고,
R11은 아미노, C1-3-알킬아미노, 디-(C1-3-알킬)-아미노, C1-4-알콕시 또는 메톡시-C1-3-알콕시 그룹 또는 5- 또는 6원의 사이클로알킬렌이미노 그룹(여기서, 피페리디노 그룹의 4 위치에서 메틸렌 그룹은 -NH, -N(C1-3-알킬) 또는 -N(C1-3-알킬-카보닐) 그룹으로 교체될 수 있다), 또는
아제티디노, 피롤리디노, 피페리디노, 2,6-디메틸-피페리디노, 3,5-디메틸-피페리디노 또는 아제피노 그룹(여기서, 피롤리디노 그룹의 3 위치에서 메틸렌 그룹은 하이드록시 그룹에 의해 치환될 수 있고, 피페리디노 그룹의 4 위치에서 메틸렌 그룹은 하이드록시, 하이드록시-C1-3-알킬 또는 C1-3-알콕시 그룹에 의해 치환될 수 있거나, 산소 또는 황 원자로, 설피닐, 설포닐, -NH, -N(C1-3-알킬), -N(C1-3-알킬-카보닐), -N(벤조일) 또는 -N(페닐-C1-3-알킬-카보닐) 그룹으로 교체될 수 있고, 피롤리디노, 피페리디노 또는 피페라지노 그룹의 이미노-질소 원자에 연결된 메틸렌 그룹은 카보닐 그룹으로 교체될 수 있다)이다.
화학식 IV
-N(R12)-CO-(CH2)p-R13
위의 화학식 IV에서,
R12는 수소 원자, C1-3-알킬 또는 페닐-C1-3-알킬 그룹이고,
p는 수 0, 1 또는 2 중의 하나이고,
R13은 아미노, C1-4-알킬아미노, 디-(C1-4-알킬)-아미노, 벤질아미노, N-(C1-3-알킬)-벤질아미노, C1-3-알콕시-C1-3-알킬아미노, N-(C1-3-알킬)-C1-3-알콕시-C1-3-알킬아미노, 디-(2-메톡시-에틸)-아미노, 디-(ω-하이드록시-C2-3-알킬)-아미노 또는 아미노카보닐-메틸-N-(메틸)-아미노 그룹,
질소 원자를 통해 결합하고, 임의로 C1-3-알킬 그룹에 의해 치환된 피롤릴, 피라졸릴 또는 이미다졸릴 그룹, 또는
C1-3-알킬, 페닐-C1-3-알킬, C1-3-알킬카보닐 또는 C1-4-알콕시카보닐 그룹에 의해 4 위치에서 임의로 치환되는 피롤리디노, 피페리디노, 모르폴리노, 티오-모르폴리노, 또는 피페라지노 그룹이거나, n이 수 1 또는 2인 경우, 또한 수소 원자일 수 있다.
화학식 V
-N(R14)-(CH2)q-(CO)r-R15
위의 화학식 V에서,
R14는 수소 원자, C1-4-알킬, C1-3-알킬-카보닐, 페닐카보닐, 페닐-C1-3-알킬카보닐, 푸릴-카보닐, 피리디닐-카보닐, 푸릴-C1-3-알킬카보닐, 피리디닐-C1-3-알킬카보닐, C1-4-알킬설포닐, 페닐설포닐 또는 페닐-C1-3-알킬설포닐 그룹이고,
q는 수 1, 2 또는 3 중의 하나이고,
r는 수 1이거나, q가 수 2 또는 3 중의 하나인 경우, 또한 수 0일 수 있고,
R15는 아미노, C1-4-알킬아미노, 디-(C1-4-알킬)-아미노, 페닐아미노, N-(C1-4-알킬)-페닐아미노, 벤질아미노 또는 N-(C1-4-알킬)-벤질-아미노 그룹이다.
화학식 VI
-N(R16)-SO2-R17
위의 화학식 VI에서,
R16은 시아노, 트리플루오로메틸-카보닐아미노 또는 N-(C1-3-알킬)-트리플루오로메틸-카보닐-아미노 그룹에 의해 임의로 말단 치환된 수소 원자 또는 C1-3-알킬 그룹이고,
R17은 C1-3-알킬 그룹이다.
특별히 언급될 만한 특히 바람직한 화학식 I의 화합물의 하나의 하위 그룹은
X, R1, R3 및 R5이 상기 정의된 바와 같고,
R2가 직쇄 또는 측쇄 C1-4-알콕시카보닐 그룹 또는 펜옥시카보닐 그룹,
삭제
알킬 잔기에서 페닐- 카복시, C1-3-알콕시카보닐, 아미노카보닐, C1-3-알킬아미노카보닐 또는 디-(C1-3-알킬)-아미노카보닐 그룹에 의해 말단 치환된 직쇄 또는 측쇄 C1-3-알콕시카보닐 그룹, 또는
알킬 잔기에서 하이드록시, C1-3-알콕시, 아미노, C1-3-알킬아미노 또는 디-(C1-3-알킬)-아미노 그룹에 의해 말단 치환된 직쇄 또는 측쇄 C2-3-알콕시-카보닐 그룹이고,
R4가 R7-(n-C1-3-알킬)-페닐 그룹이고,
R7이 아미노, C1-6-알킬아미노, 디-(C1-4-알킬)-아미노, ω-하이드록시-C2-3-알킬-아미노, N-(C1-3-알킬)-ω-하이드록시-C2-3-알킬-아미노, 디-(ω-하이드록시-C2-3-알킬)-아미노 또는 디-(ω-(C1-3-알콕시)-C2-3-알킬)-아미노 그룹, 또는
화학식 IV의 그룹에 의해 치환된 페닐 그룹인 화학식 I의 화합물, 및 이의 토오토머, 디아스테레오머, 에난티오머, 혼합물 및 염을 포함한다.
화학식 IV
-N(R12)-CO-(CH2)p-R13
위의 화학식 IV에서,
R12, p 및 R13은 상기 정의된 바와 같다.
특별히 언급될 만한 특히 바람직한 화학식 I의 화합물의 제2 하위 그룹은
X, R1, R3 및 R5가 상기 정의된 바와 같고,
R2가 아미노카보닐 또는 메틸아미노카보닐 그룹, 에틸 그룹의 2 위치에서 하이드록시 또는 C1-3-알콕시 그룹 또는 디-(C1-2-알킬)-아미노카보닐 그룹에 의해 임의로 치환된 에틸아미노카보닐 그룹이고,
R4가 R7-(n-C1-3-알킬)-페닐 그룹이고,
R7이 아미노, C1-6-알킬아미노, 디-(C1-4-알킬)-아미노, ω-하이드록시-C2-3-알킬-아미노, N-(C1-3-알킬)-ω-하이드록시-C2-3-알킬-아미노, 디-(ω-하이드록시-C2-3-알킬)-아미노 또는 디-(ω-(C1-3-알콕시)-C2-3-알킬)-아미노 그룹, 또는
화학식 IV의 그룹에 의해 치환된 페닐 그룹인 화학식 I의 화합물, 및 이의 토오토머, 디아스테레오머, 에난티오머, 혼합물 및 염을 포함한다.
화학식 IV
-N(R12)-CO-(CH2)p-R13
위의 화학식 IV에서,
R12, p 및 R13은 상기 정의된 바와 같다.
가장 바람직한 화학식 I의 화합물은
X가 산소 원자이고,
R1 및 R5가 각각 수소 원자이고,
R2가 메톡시카보닐, 에톡시카보닐 또는 아미노카보닐 그룹이고,
R3이 페닐 그룹이고,
R4가 그룹 R6로 1치환된 페닐 그룹이고,
R6이 N-메틸-이미다졸-2-일 그룹,
삭제
C1-4-알킬아미노, 디-(C1-4-알킬)-아미노, 피페리디노 또는 2,6-디메틸-피페리디노 그룹으로 말단 치환된 비측쇄 C1-3-알킬 그룹 또는
화학식 IV의 그룹 또는
화학식 V의 그룹이고,
2개 이상의 탄소 원자를 함유하는 상기 언급된 그룹에 함유된 포화된 알킬 잔기는, 달리 언급되지 않는 경우, 직쇄 또는 측쇄인 화학식 I의 화합물, 및 이의 토오토머, 디아스테레오머, 에난티오머, 혼합물 및 염을 포함한다.
화학식 IV
-N(R12)-CO-(CH2)p-R13
위의 화학식 IV에서,
R12는 C1-3-알킬 그룹이고,
p는 수 1 또는 2 중의 하나이고,
R13은 디-(C1-3-알킬)-아미노 그룹이다.
화학식 V
-N(R14)-(CH2)q-(CO)r-R15
위의 화학식 V에서,
R14은 C1-3-알킬-카보닐 또는 C1-3-알킬설포닐 그룹이고,
q는 수 1, 2 또는 3 중의 하나이고,
r은 수 1이거나, q가 수 2 또는 3 중의 하나인 경우, r은 또한 수 0이거나,
R15는 디-(C1-3-알킬)-아미노 그룹이다.
특별히 언급될 만한 가장 바람직한 화학식 I의 화합물의 하위 그룹은
X, R1, R3 및 R5가 상기 정의된 바와 같고,
R2가 메톡시카보닐 또는 에톡시카보닐 그룹이고,
R4가 디-(C1-3-알킬)-아미노-C1-3-알킬페닐 그룹 또는
화학식 IV 그룹으로 치환된 페닐 그룹인, 화학식 I의 화합물, 및 이의 토오토머, 디아스테레오머, 에난티오머, 혼합물 및 염을 포함한다.
화학식 IV
-N(R12)-CO-(CH2)p-R13
위의 화학식 IV에서,
R12, p 및 R13은 상기 정의된 바와 같다.
특히 바람직한 화합물의 예로서
(a) 3-Z-[1-(4-(피페리딘-1-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(b) 3-Z-[(1-(4-(피페리딘-1-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-카바모일-2-인돌리논
(c) 3-Z-[1-(4-(피페리딘-1-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(d) 3-Z-[1-(4-(디메틸아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(e) 3-Z-[1-(4-((2,6-디메틸-피페리딘-1-일)-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(f) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-아세틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(g) 3-Z-[1-(4-(N-(3-디메틸아미노-프로필)-N-아세틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(h) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-메틸설포닐-아미노)-아닐리노)- 1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(i) 3-Z-[1-(4-(디메틸아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(j) 3-Z-[1-(4-(N-아세틸-N-디메틸아미노카보닐메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(k) 3-Z-[1-(4-에틸아미노메틸-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(l) 3-Z-[1-(4-(1-메틸-이미다졸-2-일)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(m) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(n) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(o) 3-Z-[1-(4-(N-(3-디메틸아미노-프로필)-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(p) 3-Z-[1-(4-(N-디메틸아미노카보닐메틸-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(q) 3-Z-[1-(4-(N-((2-디메틸아미노-에틸)-카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(r) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-아세틸-아미노)-아닐리노)-1-페 닐-메틸렌]-6-메톡시카보닐-2-인돌리논 및
(s) 3-Z-[1-(4-메틸아미노메틸-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논, 이들의 토오토머, 입체이성체 또는 생리학적으로 허용되는 염이 언급된다.
화학식 I의 화합물의 또 다른 하위 그룹은
X가 산소 또는 황 원자이고,
R1이 수소 원자 또는 프로드럭 그룹, 예를 들면, C1-4-알콕시카보닐 또는 C2-4-알카노일 그룹이고,
R2가 카복시 그룹, 직쇄 또는 측쇄 C1-6-알콕시카보닐 그룹, C5-7-사이클로알콕시카보닐 또는 페닐-C1-3-알콕시카보닐 그룹, 아미노카보닐 또는 C1-2-알킬아미노카보닐 그룹이거나, R4가 아미노설포닐-페닐 또는 N-(C1-5-알킬)-C1-3-알킬아미노카보닐-페닐 그룹이 아닌 경우, 디-(C1-2-알킬)-아미노카보닐 그룹이고,
R3이 수소 원자, C1-6-알킬, C3-7-사이클로알킬, 트리플루오로메틸 또는 헤테로아릴 그룹, 또는
삭제
페닐 또는 나프틸 그룹; 플루오르, 염소, 브롬 또는 요오드 원자에 의해, 트리플루오로메틸, C1-3-알킬 또는 C1-3-알콕시 그룹에 의해 1 또는 2치환된 페닐 또는 나프틸 그룹이고, 2치환인 경우, 치환기는 동일하거나 상이할 수 있고,
여기서 상기 언급된 치환되지 않은 페닐 및 나프틸 그룹 뿐만 아니라 1 또는 2치환된 페닐 및 나프틸 그룹은 하이드록시, 하이드록시-C1-3-알킬 또는 C1-3-알콕시-C1-3-알킬 그룹에 의해; 시아노, 카복시, 카복시-C1-3-알킬, C1-3-알콕시카보닐, 아미노카보닐, C1-3-알킬아미노-카보닐 또는 디-(C1-3-알킬)-아미노카보닐 그룹에 의해; 니트로 그룹에 의해; 아미노, C1-3-알킬아미노, 디-(C1-3-알킬)-아미노 또는 아미노-C1-3-알킬 그룹에 의해; C1-3-알킬카보닐아미노, N-(C1-3-알킬)-C1-3-알킬-카보닐아미노, C1-3-알킬카보닐아미노-C1-3-알킬, N-(C1-3-알킬)-C1-3-알킬카보닐아미노-C1-3-알킬, C1-3-알킬-설포닐아미노, C1-3-알킬설포닐아미노-C1-3-알킬, N-(C1-3-알킬)-C1-3-알킬설포닐아미노-C1-3-알킬 또는 아릴-C1-3-알킬설포닐아미노 그룹에 의해; 각각 4 내지 7개의 환 원자를 갖는 사이클로알킬아미노, 사이클로알킬렌이미노, 사이클로알킬렌이미노카보닐, 사이클로알킬렌이미노-C1-3-알킬, 사이클로알킬렌이미노카보닐-C1-3-알킬 또는 사이클로알킬렌이미노설포닐-C1-3-알킬 그룹(각각의 경우, 6 또는 7원의 사이클로알킬렌이미노 그룹의 4 위치에서 메틸렌 그룹은 산소 또는 황 원자에 의해, 설피닐, 설포닐, -NH 또는 -N(C1-3-알킬) 그룹으로 교체될 수 있다), 또는 헤테로아릴 또는 헤테로아릴-C1-3-알킬 그룹에 의해 추가로 치환될 수 있고,
R4가 C3-7-사이클로알킬 그룹(여기서, 6 또는 7원의 사이클로알킬 그룹의 4 위치에서 메틸렌 그룹은 아미노, C1-3-알킬아미노 또는 디-(C1-3-알킬)-아미노 그룹으로 치환될 수 있거나, -NH 또는 -N(C1-3-알킬) 그룹으로 교체될 수 있다) 또는
삭제
그룹 R6에 의해 치환된 페닐 그룹(여기서, 당해 그룹은 플루오르, 염소, 브롬 또는 요오드 원자에 의해, C1-5-알킬, 트리플루오로메틸, C1-3-알콕시, 카복시, C1-3-알콕시카보닐, 아미노설포닐, 니트로 또는 시아노 그룹에 의해 추가로 치환될 수 있다)이고,
R6이 수소, 플루오르, 염소, 브롬 또는 요오드 원자,
삭제
시아노, 니트로, C1-5-알킬, C3-7-사이클로알킬, 트리플루오로메틸, 페닐, 테트라졸릴 또는 헤테로아릴 그룹,
1 내지 3개의 플루오르 원자에 의해 임의로 치환된 C1-3-알콕시 그룹, C1-3-알콕시-C1-3-알콕시, 페닐-C1-3-알콕시, 아미노-C2-3-알콕시, C1-3-알킬아미노-C2-3-알콕시, 디-(C1-3-알킬)-아미노-C2-3-알콕시, 페닐-C1-3-알킬아미노-C2-3-알콕시, N-(C1-3-알킬)-페닐-C1-3-알킬아미노-C2-3-알콕시, C5-7-사이클로알킬렌이미노-C2-3-알콕시 또는 C1-3-알킬머캅토 그룹,
카복시, C1-4-알콕시카보닐, 아미노카보닐, C1-3-알킬-아미노-카보닐, N-(C1-5-알킬)-C1-3-알킬아미노카보닐, 페닐-C1-3-알킬아미노-카보닐, N-(C1-3-알킬)-페닐-C1-3-알킬아미노-카보닐, 피페라지노카보닐 또는 N-(C1-3-알킬)-피페라지노카보닐 그룹,
C1-3-알킬아미노카보닐 또는 N-(C1-5-알킬)-C1-3-알킬아미노카보닐 그룹(여기서, 알킬 잔기는 카복시 또는 C1-3-알콕시카보닐 그룹에 의해 치환되거나, 디-(C1-3-알킬)-아미노, 피페라지노, N-(C1-3-알킬)-피페라지노 또는 4 내지 7원의 사이클로알킬렌이미노 그룹으로 2 또는 3 위치에서 치환된다),
4 내지 7원의 사이클로알킬렌이미노 그룹(여기서, 이미노 그룹에 연결된 메틸렌 그룹은 카보닐 또는 설포닐 그룹으로 교체되거나, 사이클로알킬렌 잔기는 페닐 환으로 융합될 수 있거나, 1 또는 2개의 수소 원자는 각각 C1-3-알킬 그룹으로 교체될 수 있고/있거나, 각각의 경우, 6 또는 7원의 사이클로알킬렌이미노 그룹의 4 위치에서 메틸렌 그룹은 카복시, C1-3-알콕시카보닐, 아미노카보닐, C1-3-알킬아미노카보닐, 디-(C1-3-알킬)-아미노카보닐, 페닐-C1-3-알킬아미노 또는 N-(C1-3-알킬)-페닐-C1-3-알킬아미노 그룹으로 치환될 수 있거나, 산소 또는 황 원자로, 설피닐, 설포닐, -NH, -N(C1-3-알킬), -N(페닐), -N(C1-3-알킬-카보닐) 또는 -N(벤조일) 그룹으로 교체될 수 있다),
하이드록시 또는 C1-3-알콕시 그룹에 의해; 아미노, C1-7-알킬아미노, 디-(C1-7-알킬)-아미노, 디-N-(C1-3-알킬)-아미노-C2-3-알킬아미노, 트리-N,N,N'-(C1-3-알킬)-아미노-C2-3-알킬아미노, 페닐아미노, N-페닐-C1-3-알킬-아미노, 페닐-C1-3-알킬아미노, N-(C1-3-알킬)-페닐-C1-3-알킬아미노 또는 디-(페닐-C1-3-알킬)-아미노 그룹에 의해; C1-3-알킬카보닐아미노, N-(C1-3-알킬)-C1-3-알킬카보닐아미노, C1-3-알콕시카보닐-C1-3-알킬아미노 또는 N-(C1-3-알킬)-C1-3-알콕시카보닐-C1-3-알킬아미노 그룹에 의해; C4-7-사이클로알킬아미노, C4-7-사이클로알킬-C1-3-알킬아미노 또는 C4-7-사이클로알케닐아미노 그룹(여기서, 환의 1 위치는 이중 결합 중에 포함되지 않고, 상기 언급된 그룹은 각각 추가로 아미노-질소 원자에서 C1-3-알킬 그룹에 의해 치환되고, 일부 또는 모든 수소 원자는 플루오르 원자로, C5-7-사이클로알킬, C2-4-알케닐 또는 C1-4-알킬 그룹으로 교체된다)에 의해; 4 내지 7원의 사이클로알킬렌이미노 그룹(여기서, 이미노 그룹에 연결된 메틸렌 그룹은 카보닐 또는 설포닐 그룹으로 교체될 수 있거나, 사이클로알킬렌 잔기는 페닐 그룹에 융합될 수 있거나, 임의로 플루오르, 염소, 브롬 또는 요오드 원자로, 니트로, C1-3-알킬, C1-3-알콕시 또는 아미노 그룹으로 교체된 옥사졸로, 이미다졸로, 티아졸로, 피리디노, 피라지노 또는 피리미디노 그룹에 융합될 수 있거나, 1 또는 2개의 수소 원자는 C1-3-알킬, C5-7-사이클로알킬 또는 페닐 그룹으로 교체될 수 있고/있거나, 각각의 경우, 6 또는 7원의 사이클로알킬렌이미노 그룹의 4 위치에서 메틸렌 그룹은 하이드록시, 카복시, C1-4-알콕시카보닐, 아미노카보닐, C1-3-알킬아미노카보닐, 디-(C1-3-알킬)-아미노카보닐, 페닐-C1-3-알킬아미노 또는 N-(C1-3-알킬)-페닐-C1-3-알킬아미노 그룹에 의해 치환될 수 있거나, 산소 또는 황 원자로, 설피닐, 설포닐, -NH, -N(C1-3-알킬), -N(페닐), -N(C1-3-알킬-카보닐) 또는 -N(벤조일) 그룹으로 교체될 수 있다)에 의해; 카복시, C1-3-알콕시카보닐, 아미노카보닐, C1-3-알킬아미노카보닐 또는 디-(C1-3-알킬)-아미노카보닐 그룹 또는 4 내지 7원의 사이클로알킬렌이미노카보닐 그룹에 의해 치환될 수 있는 C1-4-알킬 그룹,
아미노, 피롤리디노, 피페리디노, 모르폴리노, 벤조일아미노 또는 N-(C1-3-알킬)-벤조일아미노 그룹,
알킬 잔기에서 카복시 또는 C1-3-알콕시카보닐 그룹에 의해 추가로 치환되는 N-(C1-3-알킬)-C2-4-알카노일아미노 그룹,
화학식 II의 그룹 또는
화학식 III의 그룹이고,
R6 하에 언급된 그룹에서 함유된 모든 단일 결합된 또는 융합된 페닐 그룹은 플루오르, 염소, 브롬 또는 요오드 원자에 의해, C1-5-알킬, 트리플루오로메틸, C1-3-알콕시, 카복시, C1-3-알콕시카보닐, 아미노설포닐, 니트로 또는 시아노 그룹에 의해 1 또는 2치환될 수 있고, 치환체는 동일하거나 상이할 수 있거나, 페닐 그룹의 2개의 인접한 수소 원자는 메틸렌디옥시 그룹으로 교체될 수 있고,
R5은 수소 원자 또는 C1-3-알킬 그룹이고,
아릴 그룹은 플루오르, 염소, 브롬 또는 요오드 원자로, 트리플루오로메틸, C1-3-알킬 또는 C1-3-알콕시 그룹으로 임의로 1 또는 2치환될 수 있는 페닐 또는 나프틸 그룹이고,
헤테로아릴 그룹은 C1-3-알킬 그룹에 의해 임의로 치환된 모노사이클릭 5 또는 6원의 헤테로아릴 그룹이고, 6원의 헤테로아릴 그룹은 1, 2 또는 3개의 질소 원자를 함유하고, 5원의 헤테로아릴 그룹은 C1-3-알킬 그룹, 산소 또는 황 원자에 의해 임의로 치환된 이미노 그룹, 또는 C1-3-알킬 그룹, 및 산소 또는 황 원자 또는 1 또는 2개의 질소 원자로 임의로 치환된 이미노 그룹을 함유하거나, 또한 페닐 환은 2개의 인접한 탄소 원자를 통해 상기 언급된 모노사이클릭 헤테로사이클릭 그룹에 융합될 수 있고,
2개 이상의 탄소 원자를 함유하는 상기 정의된 그룹에 존재하는 포화된 알킬 및 알콕시 잔기는 또한, 달리 언급되지 않는 경우, 이의 측쇄 이성체, 예를 들면, 이소프로필, 3급 부틸 또는 이소부틸 그룹을 포함할 수 있고,
추가로 존재하는 임의의 카복시, 아미노 또는 이미노 그룹은 생체내에서 절단될 수 있는 그룹에 의해 치환될 수 있는, 화학식 I의 화합물 및 이의 이성체 및 염을 포함한다.
화학식 II
-N(R8)-CO-(CH2)n-R9
위의 화학식 II에서,
R8은 수소 원자 또는 C1-3-알킬 그룹이고,
n은 수 0, 1, 2 또는 3 중의 하나이고,
R9는 아미노, C1-4-알킬아미노, 페닐아미노, N-(C1-4-알킬)-페닐아미노, 벤질아미노, N-(C1-4-알킬)-벤질아미노 또는 디-(C1-4-알킬)-아미노 그룹, 4 내지 7원의 사이클로알킬렌이미노 그룹(여기서, 각각의 경우 6 또는 7원의 사이클로알킬렌이미노 그룹의 4 위치에서 메틸렌 그룹은 산소 또는 황 원자로, 설피닐, 설포닐, -NH, -N(C1-3-알킬), -N(페닐), -N(C1-3-알킬-카보닐) 또는 -N(벤조일) 그룹으로 교체될 수 있거나, n이 수 1, 2 또는 3 중의 하나인 경우, 또한 수소 원자일 수 있다)이다.
화학식 III
-N(R10)-(CH2)m-(CO)o-R11
위의 화학식 III에서,
R10은 수소 원자, C1-3-알킬 그룹, C1-3-알킬카보닐, 아릴카보닐, 페닐-C1-3-알킬카보닐, C1-3-알킬설포닐, 아릴설포닐 또는 페닐-C1-3-알킬설포닐 그룹이고,
m은 수 1, 2, 3 또는 4 중의 하나이고,
o은 수 0 또는 1 중의 하나이고,
R11은 아미노, C1-4-알킬아미노, 페닐아미노, N-(C1-4-알킬)-페닐아미노, 벤질아미노, N-(C1-4-알킬)-벤질아미노 또는 디-(C1-4-알킬)-아미노 그룹, 4 내지 7원의 사이클로알킬렌이미노 그룹(여기서, 사이클로알킬렌 잔기는 페닐 환에 융합될 수 있거나, 각각의 경우 6 또는 7원의 사이클로알킬렌이미노 그룹의 4 위치에서 메틸렌 그룹은 산소 또는 황 원자로, 설피닐, 설포닐, -NH, -N(C1-3-알킬), -N(페닐), -N(C1-3-알킬-카보닐) 또는 -N(벤조일) 그룹, C1-3-알콕시 그룹, 또는 C1-3-알킬 그룹으로 1 위치에서 임의로 치환될 수 있는 디-(C1-4-알킬)-아미노-C1-3-알킬아미노 그룹으로 교체될 수 있다), 또는
삭제
N-(C1-3-알킬)-C1-5-알킬설포닐아미노 또는 N-(C1-3-알킬)-페닐설포닐아미노 그룹(여기서, 알킬 잔기에서 시아노 또는 카복시 그룹에 의해 추가로 치환될 수 있다)이다.
특별히 언급되는 화학식 I의 화합물의 추가의 하위 그룹은 화학식 I의 치환된 인돌리논의 6 위치에서 치환체가 치환된 아미도 그룹을 포함하는 하위 그룹이다.
상기 예시된 화합물, 및 이의 토오토머, 입체이성체 또는 생리학적으로 허용되는 염 뿐만 아니라 제조방법은 본원에 참조로서 인용되는 WO 제01/27081호에 기재되어 있다.
본 발명의 범위에서 바람직한 상기 화학식 I에 따른 추가의 화합물은 다음 화합물이다.
(t) 3-Z-[1-(4-(2-디메틸아미노-에톡시)-아닐리노)-1-페닐-메틸렌]-6-메톡시 카보닐-2-인돌리논
(u) 3-Z-[1-(4-(N-((4-메틸-피페라진-1-일)-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(v) 3-Z-[1-(3-시아노-4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(w) 3-Z-[1-(3-메톡시-4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(x) 3-Z-[1-(4-(N-아미노메틸카보닐-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(y) 3-Z-[1-(4-(N-(N-(2-디메틸아미노-에틸)-N-메틸-아미노메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(z) 3-Z-[1-(4-(N-(디-(2-하이드록시-에틸)-아미노-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(aa) 3-Z-[1-(4-(N-(이미다졸-1-일-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(ab) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(ac) 3-Z-[1-(4-(N-((4-메틸-[1,4]디아제판-1-일)-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(ad) 3-Z-[1-(4-(N-((1-메틸-피페리딘-4-일)-메틸카보닐)-N-메틸-아미노)-아 닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(ae) 3-Z-[1-(2,3-디메틸-4-(N-((4-메틸-피페라진-1-일)-메틸카보닐)-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(af) 3-Z-[1-(4-(N-((4-메틸-피페라진-1-일)-메틸카보닐)-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(ag) 3-Z-[1-(4-(N-((4-메틸-피페라진-1-일)-카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(ah) 3-Z-[1-(4-(N-(3-디메틸아미노-프로필)-N-아세틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(ai) 3-Z-[1-(4-(N-((3-디메틸아미노-프로필)-아미노카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(aj) 3-Z-[1-아닐리노-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(ak) 3-Z-[1-(4-(N-메틸-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(al) 3-Z-[1-사이클로헥실아미노-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(am) 3-Z-[1-(4-(4-메틸피페라진-1-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-카복시-2-인돌리논,
(an) 3-Z-[1-(4-메틸아미노메틸-아닐리노)-1-페닐-메틸렌]-6-카복시-2-인돌리논,
(ao) 3-Z-[1-(4-(모르폴린-4-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-카복시- 2-인돌리논,
(ap) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-카복시-2-인돌리논,
(aq) 3-Z-[1-(4-(디-(2-하이드록시-에틸)-아미노-메틸)-아닐리노)-1-페닐-메틸렌]-6-카복시-2-인돌리논,
(ar) 3-Z-[1-(4-(N-((4-메틸-피페라진-1-일)-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-카복시-2-인돌리논,
(as) 3-Z-[1-(4-(N-(모르폴린-4-일-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-카복시-2-인돌리논,
(at) 3-Z-[1-(4-(N-(N-(2-디메틸아미노-에틸)-N-메틸-아미노메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-카복시-2-인돌리논,
(au) 3-Z-[1-(4-(2-디메틸아미노-에톡시)-아닐리노)-1-페닐-메틸렌]-6-카복시-2-인돌리논,
(av) 3-Z-[1-사이클로헥실아미노-1-페닐-메틸렌]-6-카복시-2-인돌리논,
(aw) 3-Z-[1-(4-디메틸아미노메틸-아닐리노)-1-(3-(2-카복시-에틸)-페닐)-메틸렌]-6-메톡시카보닐-2-인돌리논
(ax) 3-Z-[1-(4-(2-디메틸아미노-에틸)-아닐리노)-1-(3-(2-카복시-에틸)-페닐)-메틸렌]-6-메톡시카보닐-2-인돌리논
(ay) 3-Z-[1-(4-(1-메틸-이미다졸-2-일)-아닐리노)-1-(3-(2-카복시-에틸)-페닐)-메틸렌]-6-메톡시카보닐-2-인돌리논
(az) 3-Z-[1-(4-디메틸아미노메틸-아닐리노)-1-(4-(2-카복시-에틸)-페닐)-메틸렌]-6-메톡시카보닐-2-인돌리논
(ba) 3-Z-[1-(4-(2-디메틸아미노-에틸)-아닐리노)-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(bb) 3-Z-[1-(4-디메틸아미노메틸-아닐리노)-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(bc) 3-Z-[1-((1-메틸-피페리딘-4-일)-아미노-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(bd) 3-Z-[1-(트랜스-4-디메틸아미노-사이클로헥실아미노)-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(be) 3-Z-[1-(4-(2-디에틸아미노-에톡시)-아닐리노)-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(bf) 3-Z-[1-(4-(N-(3-디메틸아미노-프로필)-N-프로피오닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(bg) 3-Z-[1-(4-(N-((4-메틸-피페라진-1-일)-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(bh) 3-Z-[1-사이클로헥실아미노-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(bi) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-아세틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(bj) 3-Z-[1-(3-디에틸아미노메틸-아닐리노)-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(bk) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(bl) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(bm) 3-Z-[1-아닐리노-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(bn) 3-Z-[1-(4-에틸아미노메틸-아닐리노)-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(bo) 3-Z-[1-(4-((2-디에틸아미노-에틸)-아닐리노)-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(bp) 3-Z-[1-(4-(N-(3-디메틸아미노-프로필)-N-아세틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(bq) 3-Z-[1-(4-(N-메틸-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(br) 3-Z-[1-(4-메톡시카보닐-아닐리노)-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(bs) 3-Z-[1-(4-카복시-아닐리노)-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(bt) 3-Z-[1-(4-(N-(디메틸아미노-카보닐메틸)-N-메틸설포닐-아미노)-아닐리 노)-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(bu) 3-Z-[1-(4-(2-디메틸아미노-에톡시)-아닐리노)-1-페닐-메틸렌]-6-에틸카바모일-2-인돌리논
(bv) 3-Z-[1-(4-(N-((4-메틸-피페라진-1-일)-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에틸카바모일-2-인돌리논
(bw) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-에틸카바모일-2-인돌리논
(bx) 3-Z-[1-(4-(2-디메틸아미노-에톡시)-아닐리노)-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(by) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에틸카바모일-2-인돌리논
(bz) 3-Z-[1-(4-디메틸아미노메틸-아닐리노)-1-페닐-메틸렌]-6-에틸카바모일-2-인돌리논
(ca) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-아세틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에틸카바모일-2-인돌리논
(cb) 3-Z-[1-(4-(N-(3-디메틸아미노-프로필)-N-아세틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에틸카바모일-2-인돌리논
(cc) 3-Z-[1-(4-카바모일-아닐리노)-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(cd) 3-Z-[1-(4-(N-(2-디에틸아미노-에틸)-카바모일)-아닐리노)-1-페닐-메틸 렌]-6-에틸메틸카바모일-2-인돌리논
(ce) 3-Z-[1-(4-((4-메틸-피페라진-1-일)-카보닐)-아닐리노)-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(cf) 3-Z-[1-(4-((4-메틸-피페라진-1-일)-카보닐)-아닐리노)-1-페닐-메틸렌]-6-에틸카바모일-2-인돌리논
(cg) 3-Z-[1-(4-((4-에틸-피페라진-1-일)-카보닐)-아닐리노)-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(ch) 3-Z-[1-(4-(N-에틸-N-(2-디메틸아미노-에틸)-카바모일)-아닐리노)-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(ci) 3-Z-[1-(4-(N-((4-메틸-피페라진-1-일)-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-디에틸카바모일-2-인돌리논
(cj) 3-Z-[1-(4-((시스-3,5-디메틸-피페라진-1-일)-카보닐)-아닐리노)-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(ck) 3-Z-[1-(4-((4-에틸-피페라진-1-일)-카보닐)-아닐리노)-1-페닐-메틸렌]-6-에틸카바모일-2-인돌리논
(cl) 3-Z-[1-(4-(N-(2-디에틸아미노-에틸)-카바모일)-아닐리노)-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(cm) 3-Z-[1-(4-((시스-3,5-디메틸-피페라진-1-일)-카보닐)-아닐리노)-1-페닐-메틸렌]-6-에틸카바모일-2-인돌리논
(cn) 3-Z-[1-(4-(N-(3-디메틸아미노-프로필)-N-메틸설포닐-아미노)-아닐리 노)-1-페닐-메틸렌]-6-에틸카바모일-2-인돌리논
(co) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-아닐리노)-메틸렌]-6-메톡시카보닐-2-인돌리논
(cp) 3-Z-[1-(4-디메틸아미노메틸-아닐리노)-메틸렌]-6-메톡시카보닐-2-인돌리논
(cq) 3-Z-[1-(4-(N-((4-메틸-피페라진-1-일)-메틸카보닐)-N-메틸-아미노)-아닐리노)-메틸렌]-6-메톡시카보닐-2-인돌리논
(cr) 3-Z-[1-(4-(N-((4-메틸-피페라진-1-일)-메틸카보닐)-N-메틸-아미노)-아닐리노)-메틸렌]-6-에틸카바모일-2-인돌리논
(cs) 3-Z-[1-(4-디메틸아미노메틸-아닐리노)-메틸렌]-6-에틸카바모일-2-인돌리논
(ct) 3-Z-[1-(4-(피페리딘-1-일-메틸)-아닐리노)-메틸렌]-6-에틸카바모일-2-인돌리논 및
(cu) 3-Z-[1-(4-(N-(3-디메틸아미노-프로필)-N-아세틸-아미노)-아닐리노)-메틸렌]-6-에틸카바모일-2-인돌리논 및
이의 토오토머, 입체 이성체 또는 생리학적으로 허용되는 염.
당해 화합물을 WO 제01/27081호의 화합물과 동일하게 제조할 수 있고, 하기에 기재된 방법을 사용하여 제조할 수 있다.
사용된 약어:
HOBt = 1-하이드록시-1H-벤조트리아졸
TBTU = O-벤조트리아졸-1-일-N,N,N',N'-테트라메틸우로늄-테트라플루오로보레이트
DEPC = 디에틸 피로카보네이트
n.d. = 측정되지 않음
실시예 (t) 내지 (al):
하기 화학식 II의 화합물을 WO 제01/27081호에 기재된 화합물과 동일하게 제조한다.
화학식 II
* 용매:
(A): 실리카겔, 염화메틸렌/메탄올 9:1
(B): 산화알루미늄, 염화메틸렌/메탄올 20:1
(C): 실리카겔, 염화메틸렌/메탄올/암모니아 9:1:0.1
(D): 실리카겔, 염화메틸렌/메탄올/암모니아 5:1:0.01
(E): 실리카겔, 염화메틸렌/메탄올/암모니아 9:1:0.01
하기 화합물을 동일하게 제조한다.
(a1) 3-Z-(1-사이클로헥실아미노-1-페닐-메틸렌)-6-메톡시카보닐-2-인돌리논
Rf 값: 0.60(실리카겔, 염화메틸렌/메탄올 = 9:1)
융점: 236-243℃
C23H24N2O3
질량 분석: m/z = 377 [m+H]+
실시예 (am) 내지 (av)
하기 화학식 III의 화합물을 WO 제01/27081호에 기재된 화합물과 동일하게 제조한다.
화학식 III
* 용매:
(A): 역상 RP8, 메탄올/염수(5%) = 4:1
(B): 실리카겔, 염화메틸렌/메탄올 4:1
하기 화합물을 동일하게 제조한다.
(av) 3-Z-(1-사이클로헥실아민-1-페닐-메틸렌)-6-카복시-2-인돌리논,
Rf 값: 0.50(실리카겔, 염화메틸렌/메탄올 = 9:1)
융점: 347-350℃
C22H22N2O3
질량 분석: m/z = 363 [m+H]+
실시예 (aw) 내지 (az)
(aw) 3-Z-[1-(3-(디메틸아미노메틸)-아닐리노)-1-(3-(2-카복시-에틸)-페닐)-메틸렌]-6-메톡시카보닐-2-인돌리논
(ax) 3-Z-[1-(4-(2-디메틸아미노-에틸)-아닐리노)-1-(3-(2-카복시-에틸)-페닐)-메틸렌]-6-메톡시카보닐-2-인돌리논
(ay) 3-Z-[1-(4-(1-메틸-이미다졸-2-일)-아닐리노)-1-(3-(2-카복시-에틸)-페닐)-메틸렌]-6-메톡시카보닐-2-인돌리논
(az) 3-Z-[1-(4-(디메틸아미노메틸)-아닐리노)-1-(4-(2-카복시-에틸)-페닐)-메틸렌]-6-메톡시카보닐-2-인돌리논
출발 화합물의 제조
(I.1) 1-아세틸-3-(1-하이드록시-1-(3-(2-에톡시카보닐-에틸)-페닐)-메틸렌)-6-메톡시카보닐-2-인돌리논
1-아세틸-6-메톡시카보닐-2-인돌리논 6.00g, 3-(2-에톡시카보닐-에틸)-벤조산(문헌[참조: Tetrahedron 1997, 53, 7335-7340]과 동일하게 제조) 6.30g 및 TBTU 9.10g을 디메틸포름아미드 80㎖ 및 디이소프로필메틸아민 13.5㎖ 중에 용해시키고, 4.34g HOBt를 가하고, 혼합물을 12시간 동안 상온에서 교반한다. 당해 시간 후, 용매를 제거하고, 희석된 염산을 가하고, 잔여물을 염화메틸렌/메탄올으로부터 재결정화시킨다.
수율: 10.6g(이론치의 94%)
Rf 값: 0.50(실리카겔, 염화메틸렌/메탄올 = 19:1)
융점: 80-84℃
C24H23NO7
질량 분석: m/z = 438 [m+H]+
하기 화합물을 1-아세틸-6-메톡시카보닐-2-인돌리논 및 4-(2-메톡시카보닐-에틸)-벤조산(문헌[참조: Tetrahedron 1997, 53, 7335-7340]과 동일하게 제조)로부터 동일하게 제조한다.
(I.2) 1-아세틸-3-(1-하이드록시-1-(4-(2-메톡시카보닐-에틸)-페닐)-메틸렌)-6-메톡시카보닐-2-인돌리논
Rf 값: 0.60(실리카겔, 염화메틸렌/메탄올 = 19:1)
융점: 188-192℃
C23H21NO7
질량 분석: m/z = 422 [m-H]-
(II.1) 1-아세틸-3-(1-메톡시-1-(3-(2-에톡시카보닐-에틸)-페닐)-메틸렌)-6-메톡시카보닐-2-인돌리논
트리메틸옥소늄테트라플루오로보레이트 7.17g을 염화메틸렌 100㎖ 중의 1-아세틸-3-(1-하이드록시-1-(3-(2-에톡시카보닐-에틸)-페닐)-메틸렌)-6-메톡시카보닐- 2-인돌리논(출발 물질 I.1) 10.6g 및 에틸-디이소프로필아민 12.5㎖ 용액에 천천히 가한다. 4시간 동안 상온에서 교반한 다음, 추가의 트리메틸옥소늄테트라플루오로보레이트 3.50g을 가하고, 혼합물을 12시간 동안 상온에서 교반한다. 그 후, 혼합물을 물로 2회 세척하고, 유기 상을 황산마그네슘 상에 건조시키고, 용매를 제거한다. 잔여물을 용리액으로서 염화메틸렌/메탄올(97:3)을 사용하여 실리카겔 컬럼 상에 정제한다.
수율: 4.56g(이론치의 42%)
Rf 값: 0.90(실리카겔, 염화메틸렌/메탄올 = 20:1)
C25H25NO7
질량 분석: m/z = 452 [m+H]+
하기 화합물을 1-아세틸-3-(1-하이드록시-1-(4-(2-메톡시카보닐-에틸)-페닐)-메틸렌)-6-메톡시카보닐-2-인돌리논(출발 물질 I.2)으로부터 출발하여 동일하게 제조한다.
(II.2) 1-아세틸-3-(1-메톡시-1-(4-(2-메톡시카보닐-에틸)-페닐)-메틸렌)-6-메톡시카보닐-2-인돌리논
Rf 값: 0.80(실리카겔, 염화메틸렌/메탄올 = 19:1)
융점: 112-117℃
C24H23NO7
질량 분석: m/z = 438 [m+H]+
(III.1) 3-Z-[1-(4-(디메틸아미노메틸)-아닐리노)-1-(3-(2-에톡시카보닐-에틸)-페닐)-메틸렌]-6-메톡시카보닐-2-인돌리논
1-아세틸-3-(1-메톡시-1-(3-(2-에톡시카보닐-에틸)-페닐)-메틸렌)-6-메톡시카보닐-2-인돌리논(출발 물질 II.1) 1.2g 및 4-(디메틸아미노메틸)-아닐린 0.32g을 디메틸포름아미드 10㎖ 중에 용해시키고, 3일 동안 110℃에서 교반한다. 냉각 후, 용매를 증발시키고, 잔여물을 메탄올 5㎖에 흡입시키고, 에탄올 중의 20% 나트륨에틸레이트-용매 200mg을 가한다. 혼합물을 1.5시간 동안 상온에서 교반하고, 용매를 제거하고, 잔여물을 물에 흡수시키고, 수성 상을 에틸 아세테이트로 3회 추출하고, 배합된 유기 상을 황산나트륨 상에서 건조시킨다. 용매를 증발시킨 다음, 잔여물을 용리액으로서 염화메틸렌/메탄올(9:1)을 사용하는 실리카겔 컬럼 상에 정제한다.
수율: 0.33g(이론치의 35%)
Rf 값: 0.35(실리카겔, 염화메틸렌/메탄올 = 9:1)
융점: 129-134℃
C31H33N3O5
질량 분석: m/z = 528 [m+H]+
하기 화합물을 1-아세틸-3-(1-메톡시-1-(3-(2-에톡시카보닐-에틸)-페닐)-메틸렌)-6-메톡시카보닐-2-인돌리논(출발 물질 II.1)로부터 출발하여 동일하게 제조한다.
(III.2) 3-Z-[1-(4-(2-디메틸아미노-에틸)-아닐리노)-1-(3-(2-에톡시카보닐-에틸)-페닐)-메틸렌]-6-메톡시카보닐-2-인돌리논
Rf 값: 0.30(실리카겔, 염화메틸렌/메탄올 = 9:1)
융점: 174-177℃
C32H35N3O5
질량 분석: m/z = 542 [m+H]+
(III.3) 3-Z-[1-(4-(1-메틸-이미다졸-2-일)-아닐리노)-1-(3-(2-에톡시카보닐-에틸)-페닐)-메틸렌]-6-메톡시카보닐-2-인돌리논을 1-아세틸-3-(1-메톡시-1-(3-(2-에톡시카보닐-에틸)-페닐)-메틸렌)-6-메톡시카보닐-2-인돌리논(출발 물질 II.1)로부터 제조한다.
Rf 값: 0.45(실리카겔, 염화메틸렌/메탄올 = 9:1)
융점: 102℃
C32H30N4O5
질량 분석: m/z = 551 [m+H]+
(III.4) 3-Z-[1-(4-(디메틸아미노메틸)-아닐리노)-1-(4-(2-메톡시카보닐-에틸)-페닐)-메틸렌]-6-메톡시카보닐-2-인돌리논을 1-아세틸-3-(1-메톡시-1-(4-(2-메톡시카보닐-에틸)-페닐)-메틸렌)-6-메톡시카보닐-2-인돌리논(출발 물질 II.2)로부터 제조한다.
Rf 값: 0.50(실리카겔, 염화메틸렌/메탄올 = 9:1)
융점: 226-229℃
C30H31N3O5
질량 분석: m/z = 512 [m-H]-
최종 화합물의 제조
하기 화학식 IV의 화합물을 상기 언급된 출발 물질로부터 출발하여 WO 제01/27081호에 기재된 화합물과 동일하게 제조한다.
화학식 IV
* 용매:
(A): 역상 RP8, 메탄올/염수(5%) = 4:1
(B): 실리카겔, 염화메틸렌/메탄올 9:1
실시예 (ba) 내지 (cn)
출발 화합물의 제조
(IV) 3-(1-하이드록시-1-페닐-메틸렌)-6-카복시-2-인돌리논,
1-아세틸-3-(1-메톡시-1-페닐-메틸렌)-6-메톡시카보닐-2-인돌리논(WO 제01/27081호와 동일하게 제조) 11.0g을 메탄올 500㎖에 용해시키고, 160㎖ 1N 수산화나트륨 용액을 가한다. 혼합물을 1시간 동안 상온에서 교반하고, 6시간 동안 환류하에 교반한다. 그 후, 추가의 1N 수산화나트륨 용액 20㎖를 가하고, 혼합물을 추가 3시간 동안 환류하에 교반한다. 1N 염산 160㎖를 가하고, 수득된 잔여물을 여과하고, 100℃에서 건조시킨다. 잔여물을 추가의 정제없이 사용한다.
수율: 7.60g(이론치의 86%)
(V.1) 3-(1-하이드록시-1-페닐-메틸렌)-6-(N-에틸-메틸카바모일)-2-인돌리논
3-(1-하이드록시-1-페닐-메틸렌)-6-카복시-2-인돌리논(출발 물질 IV) 5.50g, TBTU 7.54g, HOBt 3.60g 및 에틸디이소프로필아민 17.1㎖를 디메틸포름아미드 200㎖에 용해시킨다. 94% N-메틸-에틸아민 용액 2.70㎖를 가하고, 혼합물을 12시간 동안 상온에서 교반한다. 그 후, 용매를 증발시키고, 잔여물을 용리액으로서 염화메틸렌/메탄올/암모니아(9:1:0.1)을 사용하는 실리카겔 컬럼 상에 정제한다.
수율: 6.10g(이론치의 97%)
Rf 값: 0.35(실리카겔, 염화메틸렌/메탄올/암모니아 = 9:1:0.1)
C19H18N2O3
질량 분석: m/z = 323 [m+H]+
하기 화합물을 3-(1-하이드록시-1-페닐-메틸렌)-6-카복시-2-인돌리논(출발 물질 IV) 및 에틸아민으로부터 동일하게 제조한다.
(V.2) 3-(1-하이드록시-1-페닐-메틸렌)-6-에틸카바모일-2-인돌리논
C18H16N2O3
질량 분석: m/z = 309 [m+H]+
최종 화합물의 제조
(ba) 3-Z-[1-(4-(2-디메틸아미노-에틸)-아닐리노)-1-페닐-메틸렌]-6-(N-에틸-메틸카바모일)-2-인돌리논
3-(1-하이드록시-1-페닐-메틸렌)-6-(N-에틸-메틸카바모일)-2-인돌리논(출발 물질 V.1) 250mg 및 4-(2-디메틸아미노-에틸)-아닐린 382mg을 테트라하이드로푸란 3㎖ 중에 용해시키고, 트리메틸실릴이미다졸 569㎖를 가하고, 혼합물을 170℃의 마이크로 오븐에서 교반한다. 냉각시킨 다음, 용매를 증발시키고, 잔여물을 물에 흡수시킨다. 잔여물을 여과하고, 90℃에서 진공 건조시킨다.
수율: 0.18g(이론치의 50%)
Rf 값: 0.30(실리카겔, 염화메틸렌/메탄올/암모니아 = 9:1:0.1)
융점: 195-200℃
C29H32N4O2
질량 분석: m/z = 469 [m+H]+
하기 화학식 V의 화합물을 상기 화합물(ba)과 동일하게 WO 제01/27081호에 기재된 방법에 따라 제조한다.
화학식 V
* 용매:
(A): 실리카겔, 염화메틸렌/메탄올 9:1
(B): 실리카겔, 염화메틸렌/메탄올/암모니아 9:1:0.1
(C): 산화알루미늄, 염화메틸렌/메탄올 9:1
(D): 산화알루미늄, 염화메틸렌/메탄올 19:1
(E): 역상 RP8, 아세토니트릴/물/트리플루오로아세트산 = 1:1:0.01
실시예 (co) 내지 (cq)
출발 화합물의 제조
(VI) 1-아세틸-3-(1-에톡시-메틸렌)-6-메톡시카보닐-2-인돌리논
1-아세틸-6-메톡시카보닐-2-인돌리논 8.00g 및 트리에틸 오르토포르메이트 17.2㎖를 아세트산 무수물 70㎖에 용해시키고, 5.5시간 동안 110℃에서 교반한다. 냉각시킨 다음, 잔여물을 여과하고, 에테르로 세척하고, 100℃에서 진공 건조시킨다.
수율: 8.80g(이론치의 89%)
Rf 값: 0.35(실리카겔, 페트롤 에테르/염화메틸렌/에틸아세테이트 = 5:4:1)
융점: 187-189℃
C15H15NO5
질량 분석: m/z = 290 [m+H]+
최종 화합물의 제조
하기 화학식 VI의 화합물을 WO 제01/27081호에 기재된 화합물과 동일하게 제조한다.
화학식 VI
* 용매:
(A): 실리카겔, 염화메틸렌/메탄올/암모니아 9:1:0.1
실시예 (cr) 내지 (cu)
출발 화합물의 제조
(VII) 3-(1-하이드록시-메틸렌)-6-카복시-2-인돌리논
1-아세틸-3-(1-에톡시-메틸렌)-6-메톡시카보닐-2-인돌리논(출발 물질 VI) 5.00g을 메탄올 150㎖ 중에 용해시키고, 1N 수산화나트륨 용액 86.4㎖를 가한다. 혼합물을 8.5시간 동안 환류시킨다. 그 후, 1N 염산 86.4㎖를 가한다. 잔여물을 여과하고, 90℃에서 건조시킨다.
수율: 2.50g(이론치의 71%)
C10H7NO4
질량 분석: m/z = 206 [m+H]+
(VIII) 3-(1-하이드록시-메틸렌)-6-에틸카바모일-2-인돌리논
3-(1-하이드록시-메틸렌)-6-카복시-2-인돌리논(출발 물질 VII) 400mg, TBTU 689mg, HOBt 291mg 및 트리에틸아민 1.35㎖를 디메틸포름아미드 20㎖ 중에 용해시킨다. 0℃에서 THF 중의 2M 에틸아민-용액 1.95㎖를 가하고, 혼합물을 추가 12시간 동안 상온에서 교반한다. 그 후, 용매를 증발시키고, 잔여물을 용리액으로서 염화메틸렌/에탄올/아세트산(5:1:0.01)을 사용하는 실리카겔 컬럼 상에서 정제한다.
수율: 160mg(이론치의 35%)
Rf 값: 0.20(실리카겔, 염화메틸렌/에탄올/아세트산 = 5:1:0.01)
융점: 146-150℃
C12H12N2O3
질량 분석: m/z = 233 [m+H]+
최종 화합물의 제조
(cr) 3-Z-[1-(4-(N-(4-메틸-피페라진-1-일-메틸카보닐)-N-메틸-아미노)-아닐리노)-메틸렌]-6-에틸카바모일-2-인돌리논
3-(1-하이드록시-메틸렌)-6-에틸카바모일-2-인돌리논(출발 물질 VIII) 160mg 및 N-[(4-메틸-피페라진-1-일)-메틸카보닐]-N-메틸-p-페닐렌디아민 543mg을 테트라하이드로푸란 3㎖ 중에 용해시키고, 트리메틸실릴이미다졸 506㎖를 가하고, 혼합물을 25분 동안 170℃의 마이크로 오븐에서 교반한다. 냉각시킨 다음, 용매를 증발시키고, 잔여물을 용리액으로서 염화메틸렌/에탄올(19:1)을 사용하는 산화알루미늄 컬럼(활성 2-3) 상에서 정제한다. 잔여물을 에테르로부터 재결정화시키고, 80℃에서 진공 건조시킨다.
수율: 0.17g(이론치의 52%)
Rf 값: 0.60(산화알루미늄, 염화메틸렌/메탄올 = 9:1)
융점: 255-260℃
C26H32N6O3
질량 분석: m/z = 477 [m+H]+
하기 화학식 VII의 화합물을 상기 화합물(ct)와 동일하게 WO 제01/27081호에 기재된 방법에 따라 제조한다.
화학식 VII
* 용매:
(A): 산화알루미늄, 염화메틸렌/메탄올 9:1
(B): 실리카겔, 염화메틸렌/에탄올/암모니아 5:2:0.01
당해 화합물의 토오토머, 입체이성체 또는 생리학적으로 허용되는 염이 또한 본 발명의 범위에 속하고, 이를 본원에 참조로서 인용되는 WO 제01/27081호에 기재된 방법을 사용하여 수득할 수 있다.
특히 바람직한 화합물은 본원에 참조로서 인용되는 WO 제04/13099호에 기재된 3-Z-[1-(4-(N-((4-메틸-피페라진-1-일)-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논의 모노에탄설포네이트 염이다.
화합물 3-Z-[1-(4-(N-((4-메틸-피페라진-1-일)-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논-모노에탄설포네이트의 대사물 및 당해 화합물 또는, 예를 들면, 전체 분자 또는 분자 상의 1개 이상의 화학적 그룹의 화학적 또는 비화학적 유도체를 통해 수득되는 당해 대사물의 프로드럭이 또한 본 발명의 범위에 속한다. 이와 관련하여, 화합물 3-Z-[1-(4-(N-((4-메틸-피페라진-1-일)-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논-모노에탄설포네이트의 대사물 및 프로드럭이 기재된 WO 제04/13099호를 참조한다.
하기 열거된 특정한 화합물은 본 발명을 설명하기 위함이고, 이로써 발명의 범위를 제한하지는 않는다.
(1) 3-Z-(1-아닐리노-1-페닐-메틸렌)-6-에톡시카보닐-2-인돌리논
(2) 3-Z-[1-(4-니트로-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(3) 3-Z-[1-(4-플루오로-아닐리노)-1-페닐-메틸렌]-6-에톡시-카보닐-2-인돌리논
(4) 3-Z-[1-(4-클로로-아닐리노)-1-페닐-메틸렌]-6-에톡시-카보닐-2-인돌리논
(5) 3-Z-[1-(4-요오도-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(6) 3-Z-[1-(4-시아노-아닐리노)-1-페닐-메틸렌]-6-에톡시-카보닐-2-인돌리 논
(7) 3-Z-[1-(4-메톡시-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(8) 3-Z-[1-(4-에톡시-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(9) 3-Z-[1-(4-트리플루오로메틸-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(10) 3-Z-[1-(4-메틸-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(11) 3-Z-[1-(4-메틸머캅토-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(12) 3-Z-[1-(4-아미노메틸-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(13) 3-Z-[1-(4-(이소프로필아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(14) 3-Z-[1-(4-(아닐리노메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(15) 3-Z-[1-(4-(프로필아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(16) 3-Z-[1-(4-(부틸아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(17) 3-Z-[1-(4-(이소부틸아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(18) 3-Z-[1-(4-(사이클로헥실아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(19) 3-Z-[1-(4-(벤질아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(20) 3-Z-[1-(4-((N-에틸-N-메틸-아미노)-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(21) 3-Z-[1-(4-((N-메틸-N-프로필-아미노)-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(22) 3-Z-[1-(4-((N-이소프로필-N-메틸-아미노)-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(23) 3-Z-[1-(4-((N-에틸-N-프로필-아미노)-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(24) 3-Z-[1-(4-((N-에틸-N-이소프로필-아미노)-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(25) 3-Z-[1-(4-(디프로필아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(26) 3-Z-[1-(4-(디이소프로필아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(27) 3-Z-[1-(4-((N-벤질-N-에틸-아미노)-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(28) 3-Z-[1-(4-(디벤질아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(29) 3-Z-[1-(4-(3,6-디하이드로-2H-피리딘-1-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(30) 3-Z-[1-(4-(3,5-디메틸-피페리딘-1-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(31) 3-Z-[1-(4-(아제판-1-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(32) 3-Z-[1-(4-(피페라진-1-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(33) 3-Z-[1-(4-(모르폴린-4-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(34) 3-Z-[1-(4-(티오모르폴린-4-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(35) 3-Z-[1-(4-(1-옥소-티오모르폴린-4-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(36) 3-Z-[1-(4-(1,1-디옥소-티오모르폴린-4-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(37) 3-Z-[1-(4-(아세틸아미노-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(38) 3-Z-[1-(4-(2-아미노-에틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(39) 3-Z-[1-(4-(2-메틸아미노-에틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(40) 3-Z-[1-(4-(2-에틸아미노-에틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(41) 3-Z-[1-(4-(2-디에틸아미노-에틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(42) 3-Z-[1-(4-(2-피페리딘-1-일-에틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(43) 3-Z-[1-(4-(2-아세틸아미노-에틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(44) 3-Z-[1-(4-(3-아미노-프로필)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(45) 3-Z-[1-(4-(3-디메틸아미노-프로필)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(46) 3-Z-[1-(4-(N-아미노메틸카보닐-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(47) 3-Z-[1-(4-(N-메틸아미노메틸카보닐-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(48) 3-Z-[1-(4-(N-에틸아미노메틸카보닐-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(49) 3-Z-[1-(4-(N-디에틸아미노메틸카보닐-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(50) 3-Z-[1-(4-(N-(피페리딘-1-일-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(51) 3-Z-[1-(4-(N-(모르폴린-4-일-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(52) 3-Z-[1-(4-(N-(피페라진-1-일-메틸카보닐)-N-메틸-아미노]-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(53) 3-Z-[1-(4-(N-(2-아미노-에틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(54) 3-Z-[1-(4-(N-(2-메틸아미노-에틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(55) 3-Z-[1-(4-(N-(2-디에틸아미노-에틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(56) 3-Z-[1-(4-(N-아세틸-N-(2-아미노에틸)-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(57) 3-Z-[1-(4-(N-아세틸-N-(2-메틸아미노-에틸)-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(58) 3-Z-[1-(4-(N-아세틸-N-(2-메틸아미노-프로필)-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(59) 3-Z-[1-(4-(N-아세틸-N-(2-피페리딘-1-일-에틸)-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(60) 3-Z-[1-(4-(N-아세틸-N-(아미노카보닐메틸)-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(61) 3-Z-[1-(4-(N-아세틸-N-(디메틸아미노카보닐메틸)-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(62) 3-Z-[1-(4-(N-아세틸-N-(피페리딘-1-일-카보닐메틸)-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(63) 3-Z-[1-(4-(N-메틸-N-(아미노카보닐)-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(64) 3-Z-[1-(4-(N-메틸-N-(메틸아미노카보닐)-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(65) 3-Z-[1-(4-(N-메틸-N-(디메틸아미노카보닐)-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(66) 3-Z-[1-(4-(N-메틸-N-(피페리딘-1-일-카보닐)-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(67) 3-Z-[1-(4-(N-(2-아미노에틸)-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(68) 3-Z-[1-(4-(N-(2-메틸아미노-에틸)-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(69) 3-Z-[1-(4-(N-(2-에틸아미노-에틸)-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(70) 3-Z-[1-(4-(N-(2-디에틸아미노-에틸)-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(71) 3-Z-[1-(4-(N-(2-피롤리딘-1-일-에틸)-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(72) 3-Z-[1-(4-(N-(2-피페리딘-1-일-에틸)-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(73) 3-Z-[1-(4-(N-(2-피페라진-1-일-에틸)-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(74) 3-Z-[1-(4-(N-(2-(모르폴린-4-일)-에틸)-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(75) 3-Z-[1-(4-(N-(아미노카보닐메틸)-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(76) 3-Z-[1-(4-(N-(메틸아미노카보닐메틸)-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(77) 3-Z-[1-(4-(N-(에틸아미노카보닐메틸)-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(78) 3-Z-[1-(4-(N-(N-(2-디메틸아미노-에틸)-N-메틸-아미노)-카보닐메틸)-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(79) 3-Z-[1-(4-(N-(디에틸아미노카보닐메틸)-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(80) 3-Z-[1-(4-(N-(피롤리딘-1-일-카보닐메틸)-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(81) 3-Z-[1-(4-(N-(피페리딘-1-일-카보닐메틸)-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(82) 3-Z-[1-(4-(N-(피페라진-1-일-카보닐메틸)-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(83) 3-Z-[1-(4-(N-((모르폴린-4-일)-카보닐메틸)-N-메틸-설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(84) 3-Z-[1-(4-(2-디메틸아미노-에톡시)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(85) 3-Z-[1-(4-(3-디메틸아미노-프로폭시)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(86) 3-Z-[1-(4-(아미노카보닐메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(87) 3-Z-[1-(4-(2-아미노카보닐-에틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(88) 3-Z-[1-(4-(피리딘-2-일)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(89) 3-Z-[1-(4-(피리딘-3-일)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(90) 3-Z-[1-(4-(피리딘-4-일)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(91) 3-Z-[1-(4-(N-아세틸-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(92) 3-Z-[1-(4-(N-에틸카보닐-N-(디메틸아미노카보닐-메틸)-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(93) 3-Z-[1-(카바모일메틸-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(94) 3-Z-[1-(4-디메틸카바모일메틸-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(95) 3-Z-[1-(4-(피페리딘-1-일-메틸)-아닐리노)-메틸렌]-6-에톡시카보닐-2-인돌리논
(96) 3-Z-[1-(4-(피페리딘-1-일-메틸)-아닐리노)-프로필리덴]-6-에톡시카보닐-2-인돌리논
(97) 3-Z-[1-(4-(피페리딘-1-일-메틸)-아닐리노)-부틸리덴]-6-에톡시카보닐-2-인돌리논
(98) 3-Z-[1-(4-(N-(3-디메틸아미노-프로필)-N-아세틸-아미노)-아닐리노)-메틸렌]-6-에톡시카보닐-2-인돌리논
(99) 3-Z-[1-(4-(N-(3-디메틸아미노-프로필)-N-아세틸-아미노)-아닐리노)-에틸리덴]-6-에톡시카보닐-2-인돌리논
(100) 3-Z-[1-(4-(N-(3-디메틸아미노-프로필)-N-아세틸-아미노)-아닐리노)-프로필리덴]-6-에톡시카보닐-2-인돌리논
(101) 3-Z-[1-(4-(N-(3-디메틸아미노-프로필)-N-아세틸-아미노)-아닐리노)-부틸리덴]-6-에톡시카보닐-2-인돌리논
(102) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-메틸설포닐-아미노)-아닐리노)-메틸렌]-6-에톡시카보닐-2-인돌리논
(103) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-메틸설포닐-아미노)-아닐리노)-프로필리덴]-6-에톡시카보닐-2-인돌리논
(104) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-메틸설포닐-아미노)-아닐리노)-부틸리덴]-6-에톡시카보닐-2-인돌리논
(105) 3-Z-[1-(4-테트라졸-5-일-아닐리노)-메틸렌]-6-에톡시카보닐-2-인돌리논
(106) 3-Z-[1-(4-테트라졸-5-일-아닐리노)-에틸리덴]-6-에톡시카보닐-2-인돌리논
(107) 3-Z-[1-(4-테트라졸-5-일-아닐리노)-프로필리덴]-6-에톡시카보닐-2-인돌리논
(108) 3-Z-[1-(4-테트라졸-5-일-아닐리노)-부틸리덴]-6-에톡시카보닐-2-인돌리논
(109) 3-Z-[1-(4-카복시-아닐리노)-메틸렌]-6-에톡시카보닐-2-인돌리논
(110) 3-Z-[1-(4-카복시-아닐리노)-프로필리덴]-6-에톡시카보닐-2-인돌리논
(111) 3-Z-[1-(4-카복시-아닐리노)-부틸리덴]-6-에톡시카보닐-2-인돌리논
(112) 3-Z-[1-(4-(N-(3-디메틸아미노-프로피오닐)-N-디메틸아미노카보닐메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(113) 3-Z-[1-(4-(N-(4-디메틸아미노-부티릴)-N-디메틸아미노카보닐메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(114) 3-Z-[1-(4-(N-디메틸아미노카보닐메틸-N-(2-디메틸아미노-에틸설포닐)-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(115) 3-Z-[1-(4-(N-디메틸아미노카보닐메틸-N-(3-디메틸아미노-프로필설포닐)-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(116) 3-Z-[1-(4-((2-하이드록시-에틸)-아미노-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(117) 3-Z-[1-(4-((2-메톡시-에틸)-아미노-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(118) 3-Z-[1-(4-((2-디메틸아미노-에틸)-아미노-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(119) 3-Z-[1-(4-((3-디메틸아미노-프로필)-아미노-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(120) 3-Z-[1-(4-((N-3급-부톡시카보닐-2-아미노-에틸)-아미노-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(121) 3-Z-[1-(4-((N-3급-부톡시카보닐-3-아미노-프로필)-아미노-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(122) 3-Z-[1-(4-((2-아미노-에틸)-아미노-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(123) 3-Z-[1-(4-((3-아미노-프로필)-아미노-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(124) 3-Z-[1-(4-((2-아세틸아미노-에틸)-아미노-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(125) 3-Z-[1-(4-((3-아세틸아미노-프로필)-아미노-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(126) 3-Z-[1-(4-((2-메틸설포닐아미노-에틸)-아미노-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(127) 3-Z-[1-(4-((3-메틸설포닐아미노-프로필)-아미노-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(128) 3-Z-[1-(4-(N-(N-3급-부톡시카보닐-2-아미노-에틸)-N-메틸-아미노-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(129) 3-Z-[1-(4-(N-(2-아미노-에틸)-N-메틸-아미노-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(130) 3-Z-[1-(4-(N-(2-아세틸아미노-에틸)-N-메틸-아미노-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(131) 3-Z-[1-(4-(N-(2-메틸설포닐아미노-에틸)-N-메틸-아미노-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(132) 3-Z-[1-(4-(카복시메틸-아미노-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(133) 3-Z-[1-(4-(에톡시카보닐메틸-아미노-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(134) 3-Z-[1-(4-(카바모일메틸-아미노-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(135) 3-Z-[1-(4-(디메틸카바모일-메틸-아미노-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(136) 3-Z-[1-(4-(메틸카바모일-메틸-아미노-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(137) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-3-아미노-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(138) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-3-니트로-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(139) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-3-아세틸아미노-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(140) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-3-메틸설포닐아미노-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(141) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-3-시아노-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(142) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-3-하이드록시-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(143) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-3-메톡시-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(144) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-3-에톡시카보닐-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(145) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-3-카복시-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(146) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-3-카바모일-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(147) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-3-클로로-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(148) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-3-플루오로-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(149) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-3-브로모-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(150) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-3-메틸-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(151) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-3-트리플루오로메틸-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(152) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-3,5-디브로모-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(153) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-3,5-디클로로-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(154) 3-Z-[1-(4-(디메틸아미노메틸)-3-아미노-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(155) 3-Z-[1-(4-(디메틸아미노메틸)-3-니트로-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(156) 3-Z-[1-(4-(디메틸아미노메틸)-3-아세틸아미노-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(157) 3-Z-[1-(4-(디메틸아미노메틸)-3-(메틸설포닐아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(158) 3-Z-[1-(4-(디메틸아미노메틸)-3-시아노-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(159) 3-Z-[1-(4-(디메틸아미노메틸)-3-하이드록시-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(160) 3-Z-[1-(4-(디메틸아미노메틸)-3-메톡시-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(161) 3-Z-[1-(4-(디메틸아미노메틸)-3-(에톡시카보닐)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(162) 3-Z-[1-(4-(디메틸아미노메틸)-3-카복시-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(163) 3-Z-[1-(4-(디메틸아미노메틸)-3-카바모일-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(164) 3-Z-[1-(4-(디메틸아미노메틸)-3-클로로-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(165) 3-Z-[1-(4-(디메틸아미노메틸)-3-플루오로-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(166) 3-Z-[1-(4-(디메틸아미노메틸)-3-브로모-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(167) 3-Z-[1-(4-(디메틸아미노메틸)-3-메틸-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(168) 3-Z-[1-(4-(디메틸아미노메틸)-3-트리플루오로메틸-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(169) 3-Z-[1-(4-(디메틸아미노메틸)-3,5-디브로모-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(170) 3-Z-[1-(4-(디메틸아미노메틸)-3,5-디클로로-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(171) 3-Z-[1-(4-(N-((4-메틸-피페라진-1-일)-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(172) 3-Z-[1-(4-(N-(이미다조-1-일-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(173) 3-Z-[1-(4-(N-(프탈이미도-2-일-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(174) 3-Z-[1-(4-(N-아미노메틸카보닐-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(175) 3-Z-[1-(4-(N-아세틸아미노메틸카보닐-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(176) 3-Z-[1-(4-(N-메틸설포닐아미노메틸카보닐-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(177) 3-Z-[1-(4-(N-((N-(2-메톡시에틸)-N-메틸-아미노)-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(178) 3-Z-[1-(4-(N-((N-(2-디메틸아미노에틸)-N-메틸-아미노)-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(179) 3-Z-[1-(4-(N-((디-(2-하이드록시에틸)-아미노)-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(180) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-아닐리노)-메틸렌]-6-에톡시카보닐-2-인돌리논
(181) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-아닐리노)-에틸리덴]-6-에톡시카보닐-2-인돌리논
(182) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-아닐리노)-프로필리덴]-6-에톡시카보닐-2-인돌리논
(183) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-아닐리노)-부틸리덴]-6-에톡시카보닐-2-인돌리논
(184) 3-Z-[1-(4-(디메틸아미노메틸)-아닐리노)-메틸렌]-6-에톡시카보닐-2-인돌리논
(185) 3-Z-[1-(4-(디메틸아미노메틸)-아닐리노)-에틸리덴]-6-에톡시카보닐-2-인돌리논
(186) 3-Z-[1-(4-(디메틸아미노메틸)-아닐리노)-프로필리덴]-6-에톡시카보닐-2-인돌리논
(187) 3-Z-[1-(4-(디메틸아미노메틸)-아닐리노)-부틸리덴]-6-에톡시카보닐-2-인돌리논
(188) 3-Z-[1-(4-(N-디메틸아미노카보닐메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(189) 3-Z-[1-(4-(N-(3-디메틸아미노-프로필)-N-아세틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(190) 3-Z-[1-(4-((이미다졸리딘-2,4-디온-5-일리덴)-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(191) 3-Z-[1-(4-(N-((2-디메틸아미노-에틸)-카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(192) 3-Z-[1-(4-(N-3급-부톡시카보닐-아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(193) 3-Z-[1-(4-(2-옥소-피롤리딘-1-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(194) 3-Z-[1-(4-(N-아미노카보닐메틸-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(195) 3-Z-[1-(4-(N-시아노메틸-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(196) 3-Z-[1-(4-(2-(이미다졸-4-일)-에틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(197) 3-Z-[1-(4-((2-(N-벤질-N-메틸-아미노)-에틸)-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(198) 3-Z-[1-(4-사이클로헥실아미노-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(199) 3-Z-[1-(4-(이미다졸-1-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(200) 3-Z-[1-(4-(이미다졸-1-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(201) 3-Z-[1-(N-메틸-피페리딘-4-일-아미노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(202) 3-Z-[1-(4-(이미다졸-4-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(203) 3-Z-[1-(4-((4-하이드록시-피페리딘-1-일)-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(204) 3-Z-[1-(4-((4-메톡시-피페리딘-1-일)-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(205) 3-Z-[1-(4-벤질-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(206) 3-Z-[1-(4-(N-(3-트리플루오로아세틸아미노-프로필)-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(207) 3-Z-[1-(4-(4-3급-부톡시카보닐-피페라진-1-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(208) 3-Z-[1-(4-(1-메틸-이미다졸-2-일)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(209) 3-Z-[1-(4-(1-메틸-이미다졸-2-일)-아닐리노)-1-페닐-메틸렌]-6-에톡 시카보닐-2-인돌리논
(210) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-메틸설포닐-아미노)-3-아미노-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(211) 3-Z-[1-(4-((3-(N-벤질-N-메틸-아미노)-프로필)-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(212) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-아세틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(213) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-부티릴-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(214) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-이소부티릴-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(215) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-벤조일-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(216) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-아세틸-아미노)-3-아미노-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(217) 3-Z-[1-(4-(4-하이드록시메틸-피페리딘-1-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(218) 3-Z-[1-(4-(2-(4-하이드록시-피페리딘-1-일)-에틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(219) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-프로필설포닐-아미노)-아닐리 노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(220) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-부틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(221) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-페닐설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(222) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-벤질설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(223) 3-Z-[1-(4-((이미다졸리딘-2,4-디온-5-일)-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(224) 3-Z-[1-(4-((3-하이드록시-피롤리딘-1-일)-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(225) 3-Z-[1-(4-(사이클로헥실일-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(226) 3-Z-[1-(4-(사이클로헥실-카보닐)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(227) 3-Z-[1-(4-디에틸아미노메틸-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(228) 3-Z-[1-(4-(N-(n-헥실)-N-메틸-아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(229) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-(푸란-2-카보닐)-아미노)-아닐 리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(230) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-(2-메톡시-벤조일)-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(231) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-(피리딘-3-카보닐)-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(232) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-(페닐-아세틸)-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(233) 3-Z-[1-(4-(이미다졸-2-일)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(234) 3-Z-[1-(4-(1-에틸-이미다졸-2-일)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(235) 3-Z-[1-(4-(1-벤질-이미다졸-2-일)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(236) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-이소프로필설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(237) 3-Z-[1-(4-(N-((4-벤질-피페라진-1-일)-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(238) 3-Z-[1-(4-(N-(피롤리딘-1-일-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(239) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-아세틸-아미노)-3-브로모-아닐 리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(240) 3-Z-[1-(4-(5-메틸-이미다졸-4-일)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(241) 3-Z-[1-(4-(N-((2-디메틸아미노-에틸)-카보닐)-N-이소프로필-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(242) 3-Z-[1-(4-(N-((2-디메틸아미노-에틸)-카보닐)-N-벤질-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(243) 3-Z-[1-(4-(N-부틸-N-3급-부톡시카보닐-아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(244) 3-Z-[1-(4-(N-((N-아미노카보닐메틸-N-메틸-아미노)-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(245) 3-Z-[1-(4-(N-((N-벤질-N-메틸-아미노)-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(246) 3-Z-[1-(4-(N-(디-(2-메톡시에틸)-아미노-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(247) 3-Z-[1-(4-(N-((2-(4-3급-부톡시카보닐-피페라진-1-일)-에틸)-카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(248) 3-Z-[1-(4-(N-((2-(피페리딘-1-일)-에틸)-카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(249) 3-Z-[1-(4-(N-((2-(N-벤질-N-메틸-아미노)-에틸)-카보닐)-N-메틸-아미 노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(250) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-이소프로필-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(251) 3-Z-[1-(4-(N-(피페리딘-1-일-메틸카보닐)-N-이소프로필-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(252) 3-Z-[1-(4-(N-((4-3급-부톡시카보닐-피페라진-1-일)-메틸카보닐)-N-이소프로필-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(253) 3-Z-[1-(4-(N-((N-벤질-N-메틸-아미노)-메틸카보닐)-N-벤질-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(254) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-벤질-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(255) 3-Z-[1-(4-(N-(피페리딘-1-일-메틸카보닐)-N-벤질-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(256) 3-Z-[1-(4-(1,2,4-트리아졸-2-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(257) 3-Z-[1-(4-(1,2,3-트리아졸-2-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(258) 3-Z-[1-(4-(1,2,3-트리아졸-1-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(259) 3-Z-[1-(4-((N-아미노카보닐메틸-N-메틸-아미노)-메틸)-아닐리노)-1- 페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(260) 3-Z-[1-(4-((디-(2-메톡시-에틸)-아미노)-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(261) 3-Z-[1-(4-((디-(2-하이드록시-에틸)-아미노)-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(262) 3-Z-[1-(4-((N-에톡시카보닐메틸-N-메틸-아미노)-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(263) 3-Z-[1-(4-(아제티딘-1-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(264) 3-Z-[1-(4-(N-프로필-N-3급-부톡시카보닐-아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(265) 3-Z-[1-(4-((N-(2-(2-메톡시-에톡시)-에틸)-N-메틸-아미노)-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(266) 3-Z-[1-(4-((N-(3급-부톡시카보닐-3-아미노-프로필)-N-메틸-아미노)-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(267) 3-Z-[1-(4-((N-(메틸카바모일-메틸)-N-메틸-아미노)-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(268) 3-Z-[1-(4-((N-(디메틸카바모일-메틸)-N-메틸-아미노)-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(269) 3-Z-[1-(4-((N-프로필-N-메틸-아미노)-메틸)-아닐리노)-1-페닐-메틸 렌]-6-에톡시카보닐-2-인돌리논
(270) 3-Z-[1-(4-((N-(2-디메틸아미노-에틸)-N-메틸-아미노)-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(271) 3-Z-[1-(4-((N-(3-디메틸아미노-프로필)-N-메틸-아미노)-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(272) 3-Z-[1-(4-((N-(2-메톡시-에틸)-N-메틸-아미노)-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(273) 3-Z-[1-(4-((N-(2-하이드록시-에틸)-N-메틸-아미노)-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(274) 3-Z-[1-(4-((N-(디옥솔란-2-일-메틸)-N-메틸-아미노)-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(275) 3-Z-[1-(4-(3-옥소-피페라진-1-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(276) 3-Z-[1-(4-(N-(피페라진-1-일-메틸카보닐)-N-이소프로필-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(277) 3-Z-[1-(4-(N-((2-(피페라진-1-일)-에틸)-카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(278) 3-Z-[1-(4-((N-(3-아미노-프로필)-N-메틸-아미노)-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(279) 3-Z-[1-(4-(N-(3-메틸아미노-프로필)-N-메틸설포닐-아미노)-아닐리 노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(280) 3-Z-[1-(4-우레이도메틸-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(281) 3-Z-[1-(4-구아니디노메틸-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(282) 3-Z-[1-(4-(N-메틸설포닐-아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(283) 3-Z-[1-(4-(4-벤조일-피페라진-1-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(284) 3-Z-[1-(4-((N-(3-아세틸아미노-프로필)-N-메틸-아미노)-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(285) 3-Z-[1-(4-((N-(3-메틸설포닐아미노-프로필)-N-메틸-아미노)-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(286) 3-Z-[1-(4-((N-카복시메틸-N-메틸-아미노)-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(287) 3-Z-(1-아닐리노-1-페닐-메틸렌)-6-메톡시카보닐-2-인돌리논
(288) 3-Z-[1-(4-니트로-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(289) 3-Z-[1-(4-플루오로-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(290) 3-Z-[1-(4-클로로-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(291) 3-Z-[1-(4-브로모-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(292) 3-Z-[1-(4-요오도-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(293) 3-Z-[1-(4-시아노-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(294) 3-Z-[1-(4-카복시-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(295) 3-Z-[1-(4-메톡시-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(296) 3-Z-[1-(4-에톡시-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(297) 3-Z-[1-(4-트리플루오로메틸-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(298) 3-Z-[1-(4-메틸머캅토-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(299) 3-Z-[1-(4-(이소프로필아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(300) 3-Z-[1-(4-(아닐리노메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(301) 3-Z-[1-(4-(이소부틸아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(302) 3-Z-[1-(4-(사이클로헥실아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(303) 3-Z-[1-(4-(벤질아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(304) 3-Z-[1-(4-((N-메틸-N-프로필-아미노)-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(305) 3-Z-[1-(4-((N-이소프로필-N-메틸-아미노)-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(306) 3-Z-[1-(4-((N-에틸-N-프로필-아미노)-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(307) 3-Z-[1-(4-((N-에틸-N-이소프로필-아미노)-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(308) 3-Z-[1-(4-(디프로필아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(309) 3-Z-[1-(4-(디이소프로필아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(310) 3-Z-[1-(4-((N-벤질-N-에틸-아미노)-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(311) 3-Z-[1-(4-(디벤질아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(312) 3-Z-[1-(4-(3,6-디하이드로-2H-피리딘-1-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(313) 3-Z-[1-(4-(3,5-디메틸-피페리딘-1-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(314) 3-Z-[1-(4-(아제판-1-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(315) 3-Z-[1-(4-(2-아미노-에틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(316) 3-Z-[1-(4-(2-메틸아미노-에틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(317) 3-Z-[1-(4-(2-에틸아미노-에틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(318) 3-Z-[1-(4-(2-디메틸아미노-에틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(319) 3-Z-[1-(4-(2-디에틸아미노-에틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(320) 3-Z-[1-(4-(2-피페리딘-1-일-에틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(321) 3-Z-[1-(4-(2-아세틸아미노-에틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(322) 3-Z-[1-(4-(3-아미노-프로필)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(323) 3-Z-[1-(4-(3-디메틸아미노-프로필)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(324) 3-Z-[1-(4-(N-아미노메틸카보닐-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(325) 3-Z-[1-(4-(N-에틸아미노메틸카보닐-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(326) 3-Z-[1-(4-(N-디에틸아미노메틸카보닐-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(327) 3-Z-[1-(4-(N-디프로필아미노메틸카보닐-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(328) 3-Z-[1-(4-(N-((N-에틸-N-메틸-아미노)-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(329) 3-Z-[1-(4-(N-((N-에틸-N-프로필-아미노)-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(330) 3-Z-[1-(4-(N-((N-메틸-N-프로필-아미노)-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(331) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-에틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(332) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-프로필-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(333) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-부틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(334) 3-Z-[1-(4-(N-(2-아미노-에틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(335) 3-Z-[1-(4-(N-(2-디에틸아미노-에틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(336) 3-Z-[1-(4-(N-아세틸-N-(2-아미노에틸)-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(337) 3-Z-[1-(4-(N-아세틸-N-(2-메틸아미노-에틸)-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(338) 3-Z-[1-(4-(N-아세틸-N-(3-메틸아미노-프로필)-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(339) 3-Z-[1-(4-(N-아세틸-N-(2-피페리딘-1-일-에틸)-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(340) 3-Z-[1-(4-(N-아세틸-N-(아미노카보닐메틸)-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(341) 3-Z-[1-(4-(N-아세틸-N-(피페리딘-1-일-카보닐메틸)-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(342) 3-Z-[1-(4-(N-메틸-N-(아미노카보닐)-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(343) 3-Z-[1-(4-(N-메틸-N-(메틸아미노카보닐)-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(344) 3-Z-[1-(4-(N-메틸-N-(디메틸아미노카보닐)-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(345) 3-Z-[1-(4-(N-메틸-N-(피페리딘-1-일-카보닐)-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(346) 3-Z-[1-(4-(N-(2-에틸아미노-에틸)-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(347) 3-Z-[1-(4-(N-(2-디에틸아미노-에틸)-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(348) 3-Z-[1-(4-(N-(2-피롤리딘-1-일-에틸)-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(349) 3-Z-[1-(4-(N-(2-피페리딘-1-일-에틸)-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(350) 3-Z-[1-(4-(N-(2-피페라진-1-일-에틸)-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(351) 3-Z-[1-(4-(N-(2-(4-모르폴린-1-일)-에틸)-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(352) 3-Z-[1-(4-(N-(에틸아미노카보닐메틸)-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(353) 3-Z-[1-(4-(N-(디에틸아미노카보닐메틸)-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(354) 3-Z-[1-(4-(N-(피롤리딘-1-일-카보닐메틸)-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(355) 3-Z-[1-(4-(N-(피페리딘-1-일-카보닐메틸)-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(356) 3-Z-[1-(4-(N-(피페라진-1-일-카보닐메틸)-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(357) 3-Z-[1-(4-(N-((모르폴린-4-일)-카보닐메틸)-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(358) 3-Z-[1-(4-(2-디메틸아미노-에톡시)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(359) 3-Z-[1-(4-(3-디메틸아미노-프로폭시)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(360) 3-Z-[1-(4-(아미노카보닐메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(361) 3-Z-[1-(4-(2-아미노카보닐-에틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(362) 3-Z-[1-(4-(피리딘-2-일)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(363) 3-Z-[1-(4-(피리딘-3-일)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(364) 3-Z-[1-(4((N-펜에틸-N-메틸-아미노)-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(365) 3-Z-[1-(4-(N-아세틸-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(366) 3-Z-[1-(4-(N-에틸카보닐-N-(디메틸아미노카보닐-메틸)-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(367) 3-Z-[1-(4-(N-메틸-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(368) 3-Z-[1-(4-카복시메틸-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(369) 3-Z-[1-(4-카바모일메틸-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(370) 3-Z-[1-(4-디메틸카바모일메틸-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(371) 3-Z-[1-(4-테트라졸-5-일-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(372) 3-Z-[1-(4-(피페리딘-1-일-메틸)-아닐리노)-메틸렌]-6-메톡시카보닐-2-인돌리논
(373) 3-Z-[1-(4-(피페리딘-1-일-메틸)-아닐리노)-에틸리덴]-6-메톡시카보닐-2-인돌리논
(374) 3-Z-[1-(4-(피페리딘-1-일-메틸)-아닐리노)-프로필리덴]-6-메톡시카보닐-2-인돌리논
(375) 3-Z-[1-(4-(피페리딘-1-일-메틸)-아닐리노)-부틸리덴]-6-메톡시카보닐-2-인돌리논
(376) 3-Z-[1-(4-(N-(3-디메틸아미노-프로필)-N-아세틸-아미노)-아닐리노)-메틸렌]-6-메톡시카보닐-2-인돌리논
(377) 3-Z-[1-(4-(N-(3-디메틸아미노-프로필)-N-아세틸-아미노)-아닐리노)-에틸리덴]-6-메톡시카보닐-2-인돌리논
(378) 3-Z-[1-(4-(N-(3-디메틸아미노-프로필)-N-아세틸-아미노)-아닐리노)-프로필리덴]-6-메톡시카보닐-2-인돌리논
(379) 3-Z-[1-(4-(N-(3-디메틸아미노-프로필)-N-아세틸-아미노)-아닐리노)-부틸리덴]-6-메톡시카보닐-2-인돌리논
(380) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-메틸설포닐-아미노)-아닐리노)-메틸렌]-6-메톡시카보닐-2-인돌리논
(381) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-메틸설포닐-아미노)-아닐리노)-에틸리덴]-6-메톡시카보닐-2-인돌리논
(382) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-메틸설포닐-아미노)-아닐리노)-프로필리덴]-6-메톡시카보닐-2-인돌리논
(383) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-메틸설포닐-아미노)-아닐리노)-부틸리덴]-6-메톡시카보닐-2-인돌리논
(384) 3-Z-[1-(4-테트라졸-5-일-아닐리노)-메틸렌]-6-메톡시-카보닐-2-인돌리논
(385) 3-Z-[1-(4-테트라졸-5-일-아닐리노)-에틸리덴]-6-메톡시-카보닐-2-인돌리논
(386) 3-Z-[1-(4-테트라졸-5-일-아닐리노)-프로필리덴]-6-메톡시-카보닐-2-인돌리논
(387) 3-Z-[1-(4-테트라졸-5-일-아닐리노)-부틸리덴]-6-메톡시-카보닐-2-인돌리논
(388) 3-Z-[1-(4-카복시-아닐리노)-메틸렌]-6-메톡시카보닐-2-인돌리논
(389) 3-Z-[1-(4-카복시-아닐리노)-에틸리덴]-6-메톡시카보닐-2-인돌리논
(390) 3-Z-[1-(4-카복시-아닐리노)-프로필리덴]-6-메톡시-카보닐-2-인돌리논
(391) 3-Z-[1-(4-카복시-아닐리노)-부틸리덴]-6-메톡시카보닐-2-인돌리논
(392) 3-Z-[1-(4-(N-벤질-N-메틸-아미노메틸)-아닐리노)-1-메틸-메틸렌]-6-메톡시카보닐-2-인돌리논
(393) 3-Z-[1-(4-(2,3,4,5-테트라하이드로-벤조(d)아제핀-3-일-메틸)-아닐리노)-1-메틸-메틸렌]-6-메톡시카보닐-2-인돌리논
(394) 3-Z-[1-(4-((벤조(1,3)디옥솔-5-일-메틸)-메틸-아미노-메틸)-아닐리노)-1-메틸-메틸렌]-6-메톡시카보닐-2-인돌리논
(395) 3-Z-[1-(4-(N-펜에틸-N-메틸-아미노메틸)-아닐리노)-1-메틸-메틸렌]-6-메톡시카보닐-2-인돌리논
(396) 3-Z-[1-(4-(N-(3,4-디메톡시-벤질)-N-메틸-아미노-메틸)-아닐리노)-1-메틸-메틸렌]-6-메톡시카보닐-2-인돌리논
(397) 3-Z-[1-(4-(N-(4-클로로-벤질)-N-메틸-아미노-메틸)-아닐리노)-1-메틸-메틸렌]-6-메톡시카보닐-2-인돌리논
(398) 3-Z-[1-(4-(N-(4-메틸벤질)-N-메틸-아미노-메틸)-아닐리노)-1-메틸-메틸렌]-6-메톡시카보닐-2-인돌리논
(399) 3-Z-[1-(4-(N-(4-플루오로-벤질)-N-메틸-아미노-메틸)-아닐리노)-1-메틸-메틸렌]-6-메톡시카보닐-2-인돌리논
(400) 3-Z-[1-(4-(N-(4-브로모-벤질)-N-메틸-아미노-메틸)-아닐리노)-1-메틸-메틸렌]-6-메톡시카보닐-2-인돌리논
(401) 3-Z-[1-(4-(N-(3-디메틸아미노-프로피오닐)-N-디메틸아미노카보닐메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(402) 3-Z-[1-(4-(N-(4-디메틸아미노-부티릴)-N-디메틸아미노카보닐메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(403) 3-Z-[1-(4-(N-디메틸아미노카보닐메틸-N-(2-디메틸아미노-에틸설포닐)-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(404) 3-Z-[1-(4-(N-디메틸아미노카보닐메틸-N-(3-디메틸아미노-프로필설포닐)-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(405) 3-Z-[1-(4-((2-하이드록시-에틸)-아미노-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(406) 3-Z-[1-(4-((2-메톡시-에틸)-아미노-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(407) 3-Z-[1-(4-((2-디메틸아미노-에틸)-아미노-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(408) 3-Z-[1-(4-((3-디메틸아미노-프로필)-아미노-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(409) 3-Z-[1-(4-((N-3급-부톡시카보닐-2-아미노-에틸)-아미노-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(410) 3-Z-[1-(4-((N-3급-부톡시카보닐-3-아미노-프로필)-아미노-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(411) 3-Z-[1-(4-((2-아미노-에틸)-아미노-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(412) 3-Z-[1-(4-((3-아미노-프로필)-아미노-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(413) 3-Z-[1-(4-((2-아세틸아미노-에틸)-아미노-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(414) 3-Z-[1-(4-((3-아세틸아미노-프로필)-아미노-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(415) 3-Z-[1-(4-((2-메틸설포닐아미노-에틸)-아미노-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(416) 3-Z-[1-(4-((3-메틸설포닐아미노-프로필)-아미노-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(417) 3-Z-[1-(4-(N-(N-3급-부톡시카보닐-2-아미노-에틸)-N-메틸-아미노-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(418) 3-Z-[1-(4-(N-(2-아미노-에틸)-N-메틸-아미노-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(419) 3-Z-[1-(4-(N-(2-아세틸아미노-에틸)-N-메틸-아미노-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(420) 3-Z-[1-(4-(N-(2-메틸설포닐아미노-에틸)-N-메틸-아미노-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(421) 3-Z-[1-(4-(카복시메틸-아미노-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(422) 3-Z-[1-(4-(에톡시카보닐메틸-아미노-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(423) 3-Z-[1-(4-(카바모일메틸-아미노-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(424) 3-Z-[1-(4-(디메틸카바모일-메틸-아미노-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(425) 3-Z-[1-(4-(메틸카바모일-메틸-아미노-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(426) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-3-아미노-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(427) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-3-니트로-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(428) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-3-아세틸아미노-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(429) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-3-메틸설포닐아미노-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(430) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-3-시아노-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(431) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-3-하이드록시-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(432) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-3-메톡시-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(433) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-3-에톡시카보닐-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(434) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-3-카복시-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(435) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-3-카바모일-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(436) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-3-클로로-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(437) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-3-플루오로-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(438) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-3-브로모-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(439) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-3-메틸-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(440) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-3-트리플루오로메틸-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(441) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-3,5-디브로모-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(442) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-3,5-디클로로-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(443) 3-Z-[1-(4-(디메틸아미노메틸)-3-아미노-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(444) 3-Z-[1-(4-(디메틸아미노메틸)-3-니트로-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(445) 3-Z-[1-(4-(디메틸아미노메틸)-3-아세틸아미노-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(446) 3-Z-[1-(4-(디메틸아미노메틸)-3-메틸설포닐아미노-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(447) 3-Z-[1-(4-(디메틸아미노메틸)-3-시아노-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(448) 3-Z-[1-(4-(디메틸아미노메틸)-3-하이드록시-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(449) 3-Z-[1-(4-(디메틸아미노메틸)-3-메톡시-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(450) 3-Z-[1-(4-(디메틸아미노메틸)-3-에톡시카보닐-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(451) 3-Z-[1-(4-(디메틸아미노메틸)-3-카복시-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(452) 3-Z-[1-(4-(디메틸아미노메틸)-3-카바모일-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(453) 3-Z-[1-(4-(디메틸아미노메틸)-3-클로로-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(454) 3-Z-[1-(4-(디메틸아미노메틸)-3-플루오로-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(455) 3-Z-[1-(4-(디메틸아미노메틸)-3-브로모-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(456) 3-Z-[1-(4-(디메틸아미노메틸)-3-메틸-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(457) 3-Z-[1-(4-(디메틸아미노메틸)-3-트리플루오로메틸-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(458) 3-Z-[1-(4-디메틸아미노메틸-3,5-디브로모-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(459) 3-Z-[1-(4-(디메틸아미노메틸)-3,5-디클로로-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(460) 3-Z-[1-(4-(디메틸아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-[(2-하이드록시-에톡시)-카보닐]-2-인돌리논
(461) 3-Z-[1-(4-(디메틸아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-[(에톡시카보닐-메톡시)-카보닐]-2-인돌리논
(462) 3-Z-[1-(4-(디메틸아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-[(카복시-메톡시)-카보닐]-2-인돌리논
(463) 3-Z-[1-(4-(디메틸아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-[(카바모일-메톡시)-카보닐]-2-인돌리논
(464) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-[(2-하이드록시-에톡시)-카보닐]-2-인돌리논
(465) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-[(에톡시카보닐-메톡시)-카보닐]-2-인돌리논
(466) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-[(카복시-메톡시)-카보닐]-2-인돌리논
(467) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-[(카바모일-메톡시)-카보닐]-2-인돌리논
(468) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-[(2-메톡시-에톡시)-카보닐]-2-인돌리논
(469) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-[(2-디메틸아미노-에톡시)-카보닐]-2-인돌리논
(470) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-[(2-(N-3급-부톡시카보닐-아미노)-에톡시)-카보닐]-2-인돌리논
(471) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-[(2-아미노-에톡시)-카보닐]-2-인돌리논
(472) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-[(2,2,2-트리플루오로에톡시)-카보닐]-2-인돌리논
(473) 3-Z-[1-(4-(N-((4-메틸-피페라진-1-일)-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(474) 3-Z-[1-(4-(N-(이미다조-1-일-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(475) 3-Z-[1-(4-(N-(프탈이미도-2-일-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(476) 3-Z-[1-(4-(N-아미노메틸카보닐-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(477) 3-Z-[1-(4-(N-아세틸아미노메틸카보닐-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(478) 3-Z-[1-(4-(N-메틸설포닐아미노메틸카보닐-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(479) 3-Z-[1-(4-(N-((N-(2-메톡시에틸)-N-메틸-아미노)-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(480) 3-Z-[1-(4-(N-((N-(2-디메틸아미노에틸)-N-메틸-아미노)-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(481) 3-Z-[1-(4-(N-((디-(2-하이드록시에틸)-아미노)-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(482) 3-Z-[1-(4-3급-부톡시카보닐메틸-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(483) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-아닐리노)-메틸렌]-6-메톡시카보닐-2-인돌리논
(484) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-아닐리노)-에틸리덴]-6-메톡시카보닐-2-인돌리논
(485) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-아닐리노)-프로필리덴]-6-메톡시카보닐-2-인돌리논
(486) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-아닐리노)-부틸리덴]-6-메톡시카보닐-2-인돌리논
(487) 3-Z-[1-(4-(디메틸아미노메틸)-아닐리노)-메틸렌]-6-메톡시카보닐-2-인돌리논
(488) 3-Z-[1-(4-(디메틸아미노메틸)-아닐리노)-에틸리덴]-6-메톡시카보닐-2-인돌리논
(489) 3-Z-[1-(4-(디메틸아미노메틸)-아닐리노)-프로필리덴]-6-메톡시카보닐-2-인돌리논
(490) 3-Z-[1-(4-(디메틸아미노메틸)-아닐리노)-부틸리덴]-6-메톡시카보닐-2-인돌리논
(491) 3-Z-[1-(4-3급-부틸옥시카보닐-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(492) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(493) 3-Z-[1-(4-(N-(3-디메틸아미노-프로필)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(494) 3-Z-[1-(4-(N-메틸-아세틸아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(495) 3-Z-[1-(4-(이미다졸-4-일)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(496) 3-Z-[1-(4-((N-(디옥솔란-2-일-메틸)-N-메틸-아미노)-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(497) 3-Z-[1-(4-(N-벤질-N-메틸-아미노-메틸)-아닐리노)-1-메틸-메틸렌]-6-카바모일-2-인돌리논
(498) 3-Z-[1-(4-(2,3,4,5-테트라하이드로-벤조(d)아제핀-3-일-메틸)-아닐리노)-1-메틸-메틸렌]-6-카바모일-2-인돌리논
(499) 3-Z-[1-(4-((벤조(1,3)디옥솔-5-일-메틸)-메틸-아미노-메틸)-아닐리노)-1-메틸-메틸렌]-6-카바모일-2-인돌리논
(500) 3-Z-[1-(4-(N-펜에틸-N-메틸-아미노-메틸)-아닐리노)-1-메틸-메틸렌]-6-카바모일-2-인돌리논
(501) 3-Z-[1-(4-(N-(3,4-디메톡시-벤질)-N-메틸-아미노-메틸)-아닐리노)-1-메틸-메틸렌]-6-카바모일-2-인돌리논
(502) 3-Z-[1-(4-(N-(4-클로로-벤질)-N-메틸-아미노-메틸)-아닐리노)-1-메틸-메틸렌]-6-카바모일-2-인돌리논
(503) 3-Z-[1-(4-(N-(4-메틸-벤질)-N-메틸-아미노-메틸)-아닐리노)-1-메틸-메틸렌]-6-카바모일-2-인돌리논
(504) 3-Z-[1-(4-(N-(4-플루오로-벤질)-N-메틸-아미노-메틸)-아닐리노)-1-메틸-메틸렌]-6-카바모일-2-인돌리논
(505) 3-Z-[1-(4-(N-(4-브로모-벤질)-N-메틸-아미노-메틸)-아닐리노)-1-메틸-메틸렌]-6-카바모일-2-인돌리논
(506) 3-Z-[1-(4-((N-(2-메톡시-에틸)-N-메틸-아미노)-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(507) 3-Z-[1-(4-(디메틸아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-[(2-아미노-에톡시)-카보닐]-2-인돌리논
(508) 3-Z-[1-(4-((N-(3-메틸설포닐아미노-프로필)-N-메틸-아미노)-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(509) 3-Z-[1-(4-(피페리딘-1-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-카바모일-2-인돌리논-트리플루오로아세테이트
(510) 3-Z-(1-아닐리노-1-페닐-메틸렌)-6-카바모일-2-인돌리논
(511) 3-Z-[1-(4-디메틸아미노메틸-아닐리노)-1-페닐-메틸렌]-6-카바모일-2-인돌리논-트리플루오로아세테이트
(512) 3-Z-[1-(4-(2-디에틸아미노-에틸)-아닐리노)-1-페닐-메틸렌]-6-카바모 일-2-인돌리논-트리플루오로아세테이트
(513) 3-Z-[1-(4-(모르폴린-4-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-카바모일-2-인돌리논-트리플루오로아세테이트
(514) 3-Z-[1-(4-(1-옥소-티오모르폴린-4-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-카바모일-2-인돌리논-트리플루오로아세테이트
(515) 3-Z-[1-(4-(1,1-디옥소-티오모르폴린-4-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-카바모일-2-인돌리논-트리플루오로아세테이트
(516) 3-Z-[1-(4-(벤질아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-카바모일-2-인돌리논-트리플루오로아세테이트
(517) 3-Z-[1-(4-(아미노-메틸)-아닐리노)-1-페닐-메틸렌]-6-카바모일-2-인돌리논-트리플루오로아세테이트
(518) 3-Z-[1-(4-(2,6-디메틸피페리딘-1-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-카바모일-2-인돌리논-트리플루오로아세테이트
(519) 3-Z-[1-(4-(피롤리딘-1-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-카바모일-2-인돌리논-트리플루오로아세테이트
(520) 3-Z-[1-(3-(디메틸아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-카바모일-2-인돌리논-트리플루오로아세테이트
(521) 3-Z-[1-(3-(N-메틸-N-에틸-아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-카바모일-2-인돌리논-트리플루오로아세테이트
(522) 3-Z-[1-(3-(메틸아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-카바모일-2- 인돌리논-트리플루오로아세테이트
(523) 3-Z-[1-(3-하이드록시메틸-아닐리노)-1-페닐-메틸렌]-6-바모일-2-인돌리논
(524) 3-Z-[1-(4-(메톡시카보닐메틸-아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-카바모일-2-인돌리논-트리플루오로아세테이트
(525) 3-Z-[1-(4-(N-메틸설포닐-N-(디메틸아미노카보닐-메틸)-아미노)-아닐리노)-1-페닐-메틸렌]-6-카바모일-2-인돌리논
(526) 3-Z-[1-(4-(N-아세틸-아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-카바모일-2-인돌리논
(527) 3-Z-[1-(3,4-디메톡시-아닐리노)-1-페닐-메틸렌]-6-카바모일-2-인돌리논
(528) 3-Z-[1-(4-(모르폴린-4-일)-아닐리노)-1-페닐-메틸렌]-6-카바모일-2-인돌리논-트리플루오로아세테이트
(529) 3-Z-[1-(4-아세틸아미노-아닐리노)-1-페닐-메틸렌]-6-카바모일-2-인돌리논
(530) 3-Z-[1-(4-아미노-아닐리노)-1-페닐-메틸렌]-6-카바모일-2-인돌리논
(531) 3-Z-[1-(4-N-메틸-N-아세틸-아미노-아닐리노)-1-페닐-메틸렌]-6-카바모일-2-인돌리논
(532) 3-Z-[1-(4-에톡시카보닐-아닐리노)-1-페닐-메틸렌]-6-카바모일-2-인돌리논
(533) 3-Z-[1-(4-카복시-아닐리노)-1-페닐-메틸렌]-6-카바모일-2-인돌리논
(534) 3-Z-[1-(4-벤질카바모일-아닐리노)-1-페닐-메틸렌]-6-카바모일-2-인돌리논
(535) 3-Z-[1-(사이클로헥실-아미노)-1-페닐-메틸렌]-6-카바모일-2-인돌리논
(536) 3-Z-[1-(4-아미노-사이클로헥실-아미노)-1-페닐-메틸렌]-6-카바모일-2-인돌리논-트리플루오로아세테이트
(537) 3-Z-[1-(N-메틸-피페리딘-4-일-아미노)-1-페닐-메틸렌]-6-카바모일-2-인돌리논-트리플루오로아세테이트
(538) 3-Z-[1-(4-(피페리딘-1-일-메틸)-아닐리노)-1-메틸-메틸렌]-6-카바모일-2-인돌리논-트리플루오로아세테이트
(539) 3-Z-[1-(3-디메틸아미노메틸-아닐리노)-1-메틸-메틸렌]-6-카바모일-2-인돌리논-트리플루오로아세테이트
(540) 3-Z-[1-(4-(N-메틸-N-벤질-아미노메틸)-아닐리노)-1-메틸-메틸렌]-6-카바모일-2-인돌리논-트리플루오로아세테이트
(541) 3-Z-[1-(4-(N-메틸설포닐-N-(2-디메틸아미노-에틸)-아미노)-아닐리노)-1-메틸-메틸렌]-6-카바모일-2-인돌리논-트리플루오로아세테이트
(542) 3-Z-[1-(4-클로로-아닐리노)-1-메틸-메틸렌]-6-카바모일-2-인돌리논
(543) 3-Z-[1-(3-클로로-아닐리노)-1-메틸-메틸렌]-6-카바모일-2-인돌리논
(544) 3-Z-[1-(4-메톡시카보닐-아닐리노)-1-메틸-메틸렌]-6-카바모일-2-인돌리논
(545) 3-Z-[1-(4-카복시-아닐리노)-1-메틸-메틸렌]-6-카바모일-2-인돌리논
(546) 3-Z-[1-(4-메틸-3-니트로-아닐리노)-1-메틸-메틸렌]-6-카바모일-2-인돌리논
(547) 3-Z-[1-(4-(피페리딘-1-일-메틸)-아닐리노)-1-프로필-메틸렌]-6-카바모일-2-인돌리논-트리플루오로아세테이트
(548) 3-Z-[1-(3-디메틸아미노메틸-아닐리노)-1-프로필-메틸렌]-6-카바모일-2-인돌리논-트리플루오로아세테이트
(549) 3-Z-[1-(4-(N-메틸-N-벤질-아미노메틸)-아닐리노)-1-프로필-메틸렌]-6-카바모일-2-인돌리논-트리플루오로아세테이트
(550) 3-Z-[1-(4-(N-메틸설포닐-N-(2-디메틸아미노-에틸)-아미노)-아닐리노)-1-프로필-메틸렌]-6-카바모일-2-인돌리논-트리플루오로아세테이트
(551) 3-Z-[1-(4-클로로-아닐리노)-1-프로필-메틸렌]-6-카바모일-2-인돌리논
(552) 3-Z-[1-(3-클로로-아닐리노)-1-프로필-메틸렌]-6-카바모일-2-인돌리논
(553) 3-Z-[1-(4-메톡시카보닐-아닐리노)-1-프로필-메틸렌]-6-카바모일-2-인돌리논
(554) 3-Z-[1-(4-카복시-아닐리노)-1-프로필-메틸렌]-6-카바모일-2-인돌리논
(555) 3-Z-[1-(4-메틸-3-니트로-아닐리노)-1-프로필-메틸렌]-6-카바모일-2-인돌리논
(556) 3-Z-[1-(3-(피페리딘-1-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-카바모일-2-인돌리논-트리플루오로아세테이트
(557) 3-Z-[1-(3-(디에틸아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-카바모일-2-인돌리논-트리플루오로아세테이트
(558) 3-Z-[1-(3-(벤질아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-카바모일-2-인돌리논-트리플루오로아세테이트
(559) 3-Z-[1-(3-(N-메틸-N-벤질-아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-카바모일-2-인돌리논-트리플루오로아세테이트
(560) 3-Z-[1-(3-(부틸아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-카바모일-2-인돌리논-트리플루오로아세테이트
(561) 3-Z-[1-(3-(아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-카바모일-2-인돌리논-트리플루오로아세테이트
(562) 3-Z-[1-(3-(N-(3-디메틸아미노프로필)-N-메틸-아미노-메틸)-아닐리노)-1-페닐-메틸렌]-6-카바모일-2-인돌리논-트리플루오로아세테이트
(563) 3-Z-[1-(3-(N-(2-디메틸아미노에틸)-N-메틸-아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-카바모일-2-인돌리논-트리플루오로아세테이트
(564) 3-Z-[1-(4-(피페리딘-1-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(565) 3-Z-[1-(4-브로모-아닐리노)-1-페닐-메틸렌]-6-에톡시-카보닐-2-인돌리논
(566) 3-Z-[1-(3-(디메틸아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(567) 3-Z-[1-(4-(디메틸아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(568) 3-Z-[1-(4-[(2,6-디메틸-피페리딘-1-일)-메틸]-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(569) 3-Z-[1-(4-(2-디메틸아미노-에틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(570) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-아세틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(571) 3-Z-[1-(4-3급-부틸옥시카보닐-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(572) 3-Z-[1-(4-(N-(3-디메틸아미노-프로필)-N-아세틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(573) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(574) 3-Z-[1-(4-(4-메틸-피페라진-1-일)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(575) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(576) 3-Z-[1-(4-(N-(3-디메틸아미노-프로필)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(577) 3-Z-[1-(4-(N-메틸-아세틸아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(578) 3-Z-[1-(4-(N-메틸-메틸설포닐아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(579) 3-Z-[1-(4-(N-(3-디메틸아미노-프로필)-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(580) 3-Z-[1-(4-(N-디메틸아미노카보닐메틸-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(581) 3-Z-[1-(4-(이미다졸-4-일)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(582) 3-Z-[1-(4-(테트라졸-5-일)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(583) 3-Z-[1-(4-(N-벤질-N-메틸-아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(584) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-프로피오닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(585) 3-Z-[1-(4-(피롤리딘-1-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(586) 3-Z-[1-(4-(N-메틸-N-펜에틸-아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(587) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(588) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-에틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(589) 3-Z-[1-(4-(N-3급-부톡시카보닐-N-에틸-아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(590) 3-Z-[1-(4-(피페리딘-1-일-메틸)-아닐리노)-1-에틸-메틸렌]-6-에톡시카보닐-2-인돌리논
(591) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-메틸설포닐-아미노)-아닐리노)-1-에틸-메틸렌]-6-에톡시카보닐-2-인돌리논
(592) 3-Z-[1-(4-(디메틸아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(593) 3-Z-[1-(4-[(2,6-디메틸-피페리딘-1-일)-메틸]-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(594) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(595) 3-Z-[1-(4-(N-(3-디메틸아미노-프로필)-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(596) 3-Z-[1-(4-(N-디메틸아미노카보닐메틸-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(597) 3-Z-[1-(4-(N-아세틸-N-디메틸아미노카보닐메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(598) 3-Z-[1-(4-(N-디메틸아미노카보닐메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(599) 3-Z-[1-(4-(N-(3-디메틸아미노-프로필)-N-아세틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(600) 3-Z-[1-(4-(N-메틸아미노카보닐메틸-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(601) 3-Z-[1-(4-((이미다졸리딘-2,4-디온-5-일리덴)-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(602) 3-Z-[1-(4-(N-((2-디메틸아미노-에틸)-카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(603) 3-Z-[1-(4-(N-3급-부톡시카보닐-아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(604) 3-Z-[1-(4-(2-옥소-피롤리딘-1-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(605) 3-Z-[1-(4-(N-아미노카보닐메틸-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(606) 3-Z-[1-(4-(티오모르폴린-4-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(607) 3-Z-[1-(4-(1,1-디옥소-티오모르폴린-4-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(608) 3-Z-[1-(4-(N-시아노메틸-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(609) 3-Z-[1-(4-(N-3급-부톡시카보닐-에틸아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(610) 3-Z-[1-(4-(N-벤질-N-메틸-아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(611) 3-Z-[1-(4-(1-옥소-티오모르폴린-4-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(612) 3-Z-[1-(4-(2-(이미다졸-4-일)-에틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(613) 3-Z-[1-(4-(모르폴린-4-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(614) 3-Z-[1-(4-((4-메틸-피페라진-1-일)-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(615) 3-Z-[1-(4-((2-(N-벤질-N-메틸-아미노)-에틸)-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(616) 3-Z-[1-(4-사이클로헥실아미노-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(617) 3-Z-[1-(4-(피리딘-4-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(618) 3-Z-[1-(4-(이미다졸-1-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(619) 3-Z-[1-(4-(이미다졸-1-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(620) 3-Z-[1-(N-메틸-피페리딘-4-일-아미노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(621) 3-Z-[1-(4-(이미다졸-4-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(622) 3-Z-[1-(4-((4-하이드록시-피페리딘-1-일)-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(623) 3-Z-[1-(4-((4-메톡시-피페리딘-1-일)-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(624) 3-Z-[1-(4-벤질-아닐리노)-1-페닐-메틸렌]-6-메톡시-카보닐-2-인돌리논
(625) 3-Z-[1-(4-(N-(3-트리플루오로아세틸아미노-프로필)-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(626) 3-Z-[1-(4-3급-부톡시카보닐메틸-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(627) 3-Z-[1-(4-3급-부톡시카보닐-아닐리노)-1-에틸-메틸렌]-6-에톡시카보닐-2-인돌리논
(628) 3-Z-[1-(4-(4-3급-부톡시카보닐-피페라진-1-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(629) 3-Z-[1-(4-(1-메틸-이미다졸-2-일)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(630) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-메틸설포닐-아미노)-3-니트로-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(631) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-메틸설포닐-아미노)-3-아미노-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(632) 3-Z-[1-(4-((3-(N-벤질-N-메틸-아미노)-프로필)-N-메틸-설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(633) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-메틸설포닐-아미노)-3-클로로-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(634) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(635) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-아세틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(636) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-프로피오닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(637) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-부티릴-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(638) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-이소부티릴-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(639) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-벤조일-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(640) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-아세틸-아미노)-3-아미노-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(641) 3-Z-[1-(4-(4-하이드록시메틸-피페리딘-1-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(642) 3-Z-[1-(4-(2-(4-하이드록시-피페리딘-1-일)-에틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(643) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-프로필설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(644) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-부틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(645) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-페닐설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(646) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-벤질설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(647) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-에틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(648) 3-Z-[1-(4-((이미다졸리딘-2,4-디온-5-일)-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(649) 3-Z-[1-(4-((3-하이드록시-피롤리딘-1-일)-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(650) 3-Z-[1-(4-(사이클로헥실일-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(651) 3-Z-[1-(4-(사이클로헥실-카보닐)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(652) 3-Z-[1-(4-디에틸아미노메틸-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(653) 3-Z-[1-(4-(N-(n-헥실)-N-메틸-아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(654) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-(푸란-2-카보닐)-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(655) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-(2-메톡시-벤조일)-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시-카보닐-2-인돌리논
(656) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-(피리딘-3-카보닐)-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(657) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-(페닐-아세틸)-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(658) 3-Z-[1-(4-(N-에틸-N-메틸-아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(659) 3-Z-[1-(4-(이미다졸-2-일)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(660) 3-Z-[1-(4-(1-에틸-이미다졸-2-일)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(661) 3-Z-[1-(4-(1-벤질-이미다졸-2-일)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(662) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-이소프로필설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(663) 3-Z-[1-(4-(N-(피페리딘-1-일-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(664) 3-Z-[1-(4-(N-(모르폴린-4-일-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(665) 3-Z-[1-(4-(N-((4-벤질-피페라진-1-일)-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(666) 3-Z-[1-(4-(N-(피롤리딘-1-일-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(667) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-아세틸-아미노)-3-브로모-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(668) 3-Z-[1-(4-(5-메틸-이미다졸-4-일)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(669) 3-Z-[1-(4-(N-((2-디메틸아미노-에틸)-카보닐)-N-이소프로필-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(670) 3-Z-[1-(4-(N-((2-디메틸아미노-에틸)-카보닐)-N-벤질-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(671) 3-Z-[1-(4-(N-부틸-N-3급-부톡시카보닐-아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(672) 3-Z-[1-(4-(N-((N-아미노카보닐메틸-N-메틸-아미노)-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(673) 3-Z-[1-(4-(N-((N-벤질-N-메틸-아미노)-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(674) 3-Z-[1-(4-(N-(디-(2-메톡시에틸)-아미노-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(675) 3-Z-[1-(4-(N-((2-(4-3급-부톡시카보닐-피페라진-1-일)-에틸)-카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(676) 3-Z-[1-(4-(N-((2-(피페리딘-1-일)-에틸)-카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(677) 3-Z-[1-(4-(N-((2-(N-벤질-N-메틸-아미노)-에틸)-카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(678) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-이소프로필-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(679) 3-Z-[1-(4-(N-(피페리딘-1-일-메틸카보닐)-N-이소프로필-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(680) 3-Z-[1-(4-(N-((4-3급-부톡시카보닐-피페라진-1-일)-메틸카보닐)-N-이소프로필-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(681) 3-Z-[1-(4-(N-((N-벤질-N-메틸-아미노)-메틸카보닐)-N-벤질-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(682) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-벤질-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(683) 3-Z-[1-(4-(N-(피페리딘-1-일-메틸카보닐)-N-벤질-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(684) 3-Z-[1-(4-(1,2,4-트리아졸-2-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(685) 3-Z-[1-(4-(1,2,3-트리아졸-2-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(686) 3-Z-[1-(4-(1,2,3-트리아졸-1-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(687) 3-Z-[1-(4-((N-아미노카보닐메틸-N-메틸-아미노)-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(688) 3-Z-[1-(4-((디-(2-메톡시-에틸)-아미노)-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(689) 3-Z-[1-(4-(피롤리딘-1-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(690) 3-Z-[1-(4-((디-(2-하이드록시-에틸)-아미노)-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(691) 3-Z-[1-(4-((N-에톡시카보닐메틸-N-메틸-아미노)-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(692) 3-Z-[1-(4-(아제티딘-1-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(693) 3-Z-[1-(4-(N-프로필-N-3급-부톡시카보닐-아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(694) 3-Z-[1-(4((N-(2-(2-메톡시-에톡시)-에틸)-N-메틸-아미노)-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(695) 3-Z-[1-(4-((N-(3급-부톡시카보닐-3-아미노-프로필)-N-메틸-아미노)-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(696) 3-Z-[1-(4-((N-(메틸카바모일-메틸)-N-메틸-아미노)-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(697) 3-Z-[1-(4-((N-(디메틸카바모일-메틸)-N-메틸-아미노)-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(698) 3-Z-[1-(4-메틸-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(699) 3-Z-[1-(4-((N-프로필-N-메틸-아미노)-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(700) 3-Z-[1-(4-((N-(2-하이드록시-에틸)-N-메틸-아미노)-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(701) 3-Z-[1-(4-((N-(2-디메틸아미노-에틸)-N-메틸-아미노)-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(702) 3-Z-[1-(4-((N-(3-디메틸아미노-프로필)-N-메틸-아미노)-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(703) 3-Z-[1-(4-(3-옥소-피페라진-1-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(704) 3-Z-[1-(4-카복시-아닐리노)-1-페닐-메틸렌]-6-에톡시-카보닐-2-인돌리논
(705) 3-Z-[1-(4-아미노메틸-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(706) 3-Z-[1-(4-에틸아미노메틸-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(707) 3-Z-[1-(4-카복시메틸-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(708) 3-Z-[1-(4-카복시-아닐리노)-1-에틸-메틸렌]-6-에톡시-카보닐-2-인돌리논
(709) 3-Z-[1-(4-(피페라진-1-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(710) 3-Z-[1-(4-부틸아미노메틸-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(711) 3-Z-[1-(4-에틸아미노메틸-아닐리노)-1-페닐-메틸렌]-6-에톡시카보닐-2-인돌리논
(712) 3-Z-[1-(4-에틸아미노메틸-아닐리노)-1-페닐-메틸렌]-6-카바모일-2-인돌리논
(713) 3-Z-[1-(4-(N-(피페라진-1-일-메틸카보닐)-N-이소프로필-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(714) 3-Z-[1-(4-(N-((2-(피페라진-1-일)-에틸)-카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(715) 3-Z-[1-(4-(N-프로필-아미노메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(716) 3-Z-[1-(4-((N-(3-아미노-프로필)-N-메틸-아미노)-메틸)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(717) 3-Z-[1-(4-(2-디메틸아미노-에톡시)-아닐리노)-1-페닐-메틸렌]-6-메톡 시카보닐-2-인돌리논
(718) 3-Z-[1-(3-시아노-4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(719) 3-Z-[1-(3-메톡시-4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(720) 3-Z-[1-(4-(N-아미노메틸카보닐-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(721) 3-Z-[1-(4-(N-(N-(2-디메틸아미노-에틸)-N-메틸-아미노메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(722) 3-Z-[1-(4-(N-(디-(2-하이드록시-에틸)-아미노-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(723) 3-Z-[1-(4-(N-(이미다졸-1-일-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(724) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(725) 3-Z-[1-(4-(N-((4-메틸-[1,4]디아제판-1-일)-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(726) 3-Z-[1-(4-(N-((1-메틸-피페리딘-4-일)-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(727) 3-Z-[1-(2,3-디메틸-4-(N-((4-메틸-피페라진-1-일)-메틸카보닐)-아미 노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(728) 3-Z-[1-(4-(N-((4-메틸-피페라진-1-일)-메틸카보닐)-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(729) 3-Z-[1-(4-(N-((4-메틸-피페라진-1-일)-카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(730) 3-Z-[1-(4-(N-(3-디메틸아미노-프로필)-N-아세틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(731) 3-Z-[1-(4-(N-((3-디메틸아미노-프로필)-아미노카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(732) 3-Z-[1-아닐리노-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(733) 3-Z-[1-(4-(N-메틸-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(734) 3-Z-[1-사이클로헥실아미노-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논
(735) 3-Z-[1-(4-(4-메틸피페라진-1-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-카복시-2-인돌리논,
(736) 3-Z-[1-(4-메틸아미노메틸-아닐리노)-1-페닐-메틸렌]-6-카복시-2-인돌리논,
(737) 3-Z-[1-(4-(모르폴린-4-일-메틸)-아닐리노)-1-페닐-메틸렌]-6-카복시-2-인돌리논,
(738) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-카복시-2-인돌리논,
(739) 3-Z-[1-(4-(디-(2-하이드록시-에틸)-아미노-메틸)-아닐리노)-1-페닐-메틸렌]-6-카복시-2-인돌리논,
(740) 3-Z-[1-(4-(N-((4-메틸-피페라진-1-일)-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-카복시-2-인돌리논,
(741) 3-Z-[1-(4-(N-(모르폴린-4-일-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-카복시-2-인돌리논,
(742) 3-Z-[1-(4-(N-(N-(2-디메틸아미노-에틸)-N-메틸-아미노메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-카복시-2-인돌리논,
(743) 3-Z-[1-(4-(2-디메틸아미노-에톡시)-아닐리노)-1-페닐-메틸렌]-6-카복시-2-인돌리논,
(744) 3-Z-[1-사이클로헥실아미노-1-페닐-메틸렌]-6-카복시-2-인돌리논,
(745) 3-Z-[1-(4-디메틸아미노메틸-아닐리노)-1-(3-(2-카복시-에틸)-페닐)-메틸렌]-6-메톡시카보닐-2-인돌리논
(746) 3-Z-[1-(4-(2-디메틸아미노-에틸)-아닐리노)-1-(3-(2-카복시-에틸)-페닐)-메틸렌]-6-메톡시카보닐-2-인돌리논
(747) 3-Z-[1-(4-(1-메틸-이미다졸-2-일)-아닐리노)-1-(3-(2-카복시-에틸)-페닐)-메틸렌]-6-메톡시카보닐-2-인돌리논
(748) 3-Z-[1-(4-디메틸아미노메틸-아닐리노)-1-(4-(2-카복시-에틸)-페닐)- 메틸렌]-6-메톡시카보닐-2-인돌리논
(749) 3-Z-[1-(4-(2-디메틸아미노-에틸)-아닐리노)-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(750) 3-Z-[1-(4-디메틸아미노메틸-아닐리노)-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(751) 3-Z-[1-((1-메틸-피페리딘-4-일)-아미노-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(752) 3-Z-[1-(트랜스-4-디메틸아미노-사이클로헥실아미노)-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(753) 3-Z-[1-(4-(2-디에틸아미노-에톡시)-아닐리노)-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(754) 3-Z-[1-(4-(N-(3-디메틸아미노-프로필)-N-프로피오닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(755) 3-Z-[1-(4-(N-((4-메틸-피페라진-1-일)-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(756) 3-Z-[1-사이클로헥실아미노-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(757) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-아세틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(758) 3-Z-[1-(3-디에틸아미노메틸-아닐리노)-1-페닐-메틸렌]-6-에틸메틸카 바모일-2-인돌리논
(759) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(760) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(761) 3-Z-[1-아닐리노-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(762) 3-Z-[1-(4-에틸아미노메틸-아닐리노)-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(763) 3-Z-[1-(4-((2-디에틸아미노-에틸)-아닐리노)-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(764) 3-Z-[1-(4-(N-(3-디메틸아미노-프로필)-N-아세틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(765) 3-Z-[1-(4-(N-메틸-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(766) 3-Z-[1-(4-메톡시카보닐-아닐리노)-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(767) 3-Z-[1-(4-카복시-아닐리노)-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(768) 3-Z-[1-(4-(N-(디메틸아미노-카보닐메틸)-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(769) 3-Z-[1-(4-(2-디메틸아미노-에톡시)-아닐리노)-1-페닐-메틸렌]-6-에틸카바모일-2-인돌리논
(770) 3-Z-[1-(4-(N-((4-메틸-피페라진-1-일)-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에틸카바모일-2-인돌리논
(771) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-에틸카바모일-2-인돌리논
(772) 3-Z-[1-(4-(2-디메틸아미노-에톡시)-아닐리노)-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(773) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에틸카바모일-2-인돌리논
(774) 3-Z-[1-(4-디메틸아미노메틸-아닐리노)-1-페닐-메틸렌]-6-에틸카바모일-2-인돌리논
(775) 3-Z-[1-(4-(N-(2-디메틸아미노-에틸)-N-아세틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에틸카바모일-2-인돌리논
(776) 3-Z-[1-(4-(N-(3-디메틸아미노-프로필)-N-아세틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-에틸카바모일-2-인돌리논
(777) 3-Z-[1-(4-카바모일-아닐리노)-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(778) 3-Z-[1-(4-(N-(2-디에틸아미노-에틸)-카바모일)-아닐리노)-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(779) 3-Z-[1-(4-((4-메틸-피페라진-1-일)-카보닐)-아닐리노)-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(780) 3-Z-[1-(4-((4-메틸-피페라진-1-일)-카보닐)-아닐리노)-1-페닐-메틸렌]-6-에틸카바모일-2-인돌리논
(781) 3-Z-[1-(4-((4-에틸-피페라진-1-일)-카보닐)-아닐리노)-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(782) 3-Z-[1-(4-(N-에틸-N-(2-디메틸아미노-에틸)-카바모일)-아닐리노)-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(783) 3-Z-[1-(4-(N-((4-메틸-피페라진-1-일)-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-디에틸카바모일-2-인돌리논
(784) 3-Z-[1-(4-((시스-3,5-디메틸-피페라진-1-일)-카보닐)-아닐리노)-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(785) 3-Z-[1-(4-((4-에틸-피페라진-1-일)-카보닐)-아닐리노)-1-페닐-메틸렌]-6-에틸카바모일-2-인돌리논
(786) 3-Z-[1-(4-(N-(2-디에틸아미노-에틸)-카바모일)-아닐리노)-1-페닐-메틸렌]-6-에틸메틸카바모일-2-인돌리논
(787) 3-Z-[1-(4-((시스-3,5-디메틸-피페라진-1-일)-카보닐)-아닐리노)-1-페닐-메틸렌]-6-에틸카바모일-2-인돌리논
(788) 3-Z-[1-(4-(N-(3-디메틸아미노-프로필)-N-메틸설포닐-아미노)-아닐리노)-1-페닐-메틸렌]-6-에틸카바모일-2-인돌리논
(789) 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-아닐리노)-메틸렌]-6-메톡시카보닐-2-인돌리논
(790) 3-Z-[1-(4-디메틸아미노메틸-아닐리노)-메틸렌]-6-메톡시카보닐-2-인돌리논
(791) 3-Z-[1-(4-(N-((4-메틸-피페라진-1-일)-메틸카보닐)-N-메틸-아미노)-아닐리노)-메틸렌]-6-메톡시카보닐-2-인돌리논
(792) 3-Z-[1-(4-(N-((4-메틸-피페라진-1-일)-메틸카보닐)-N-메틸-아미노)-아닐리노)-메틸렌]-6-에틸카바모일-2-인돌리논
(793) 3-Z-[1-(4-디메틸아미노메틸-아닐리노)-메틸렌]-6-에틸카바모일-2-인돌리논
(794) 3-Z-[1-(4-(피페리딘-1-일-메틸)-아닐리노)-메틸렌]-6-에틸카바모일-2-인돌리논
(795) 3-Z-[1-(4-(N-(3-디메틸아미노-프로필)-N-아세틸-아미노)-아닐리노)-메틸렌]-6-에틸카바모일-2-인돌리논 뿐만 아니라 이의 토오토머, 입체이성체 또는 생리학적으로 허용되는 염.
따라서, 화학식 I의 화합물, 및 이의 토오토머, 이의 입체이성체 또는 이의 생리학적으로 허용되는 염은 다음으로 이루어진 그룹으로부터 선택된 특정 섬유성 질환의 예방 또는 치료에 적합하다:
만성 폐쇄성 폐질환(COPD), 만성 기관지염 및 폐기종에서의 폐 조직의 섬유증 및 리모델링;
이에 제한되지는 않지만, 특발성 폐 섬유증(IPF), 거대 세포 사이질 폐렴(GIP), 사르코이드증, 낭성 섬유증, 호흡 곤란 증후군(ARDS), 육아종증, 규폐증, 약물 유발 폐 섬유증(예를 들어, 블레오마이신, 비스-클로로니트로소우레아, 사이클로포스파미드, 아미오다론(amiodarone), 프로카인아미드, 페니실라민, 금 또는 니트로퓨란토인과 같은 약물에 의해 유발된다), 규폐증, 석면증, 전신 경피증을 포함하는, 섬유성 성분을 갖는 폐 섬유증 및 폐 질환;
천식에서의 섬유증 및 리모델링;
류마티스 관절염에서의 섬유증;
바이러스 유발 간경화증, 예를 들어 C형 간염;
방사선 유발 섬유증;
재협착, 후 혈관성형;
만성 사구체신염, 사이클로스포린을 수용하는 환자의 신장 섬유증 및 고혈압에 기인한 신장 섬유증을 포함하는 신장 질환;
섬유성 성분을 갖는 피부 질환은 이에 제한되지는 않지만, 경피증, 사르코이드증, 전신 홍반 루푸스;
과다 흉터 형성을 포함한다.
본 발명에 따른 바람직한 양태에서, 화학식 I의 화합물, 및 이의 토오토머, 이의 디아스테레오머 또는 이의 생리학적으로 허용되는 염은 특히 특발성 폐 섬유증의 예방 또는 치료에 적합하다.
생물학적 활성
하기의 실험 결과는 본 발명의 범주를 제한하지 않으면서 본 발명을 설명한다.
실시예 B1:
실시예 B1의 다음의 실험에서, 실시예 A는 화합물 3-Z-[1-(4-(N-디메틸아미노메틸카보닐-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논을 나타내고, 이는 화합물 목록의 화합물 (m)이고 바람직한 화합물 목록의 화합물 (b)이다.
(A) 블레오마이신 유발 폐 섬유증에 따른 폐 손상에 대한 대표적인 화합물의 영향
물질 및 방법
블레오마이신 설페이트(Bleomycin HEXAL™)를 지역의 약국에서 구매하였다.
블레오마이신 투여 및 치료 프로토콜
모든 실험을 동물 복지에 대한 독일 가이드라인(German guidelines for animal welfare)에 따라, 동물을 연구하도록 보증되고 신뢰할 수 있는 권위자에 의해 승인된 자에 의해 수행하였다. 수컷 위스타 래트(Male Wistar rats)에 블레오마이신 설페이트(300㎕ 식염수 내의 체중 1 kg 당 10 U) 또는 식염수만을(식염수 대조군) 카테터(catheter)(0.5mm 내부 직경, 1.0mm 외부 직경)를 사용하여 비강 통로를 통해 기관내 주입하고, 마취제 이소플루오란에 5분 동안 노출시켰다. 다음 날, 래트에 실시예 A(화합물 (m)) 또는 1ml 0.1% 나트로졸(Natrosol)에 현탁된 식염수를 경구적으로 처리하였다. 대조군 래트에 1ml 0.1% 나트로졸(비이클 대조군)을 투여하였다.
총 25마리의 래트를 연구하고 분류하고 표 1 에 나타난 바와 같이 처리하였다.
기관내 점적 주입 | 동물의 수 | 화합물 | 처리 일정 |
블레오마이신 10U /kg | 10 | 실시예 A (화합물 (m)) | 1-21일 |
블레오마이신 10U /kg | 10 | 비이클 단독 | 1-21일 |
Saline (300㎕) | 5 | 비이클 단독 | 1-21일 |
블레오마이신 점적 주입(instillation)으로부터 21일 이후, 래트를 치사량의 Narcoren™(Pentobarbital Sodium, Rhone Merieux)의 복막내 주입으로 죽였다. 이후 폐를 제거하고, 건조시키고(blotted dry) 절반을 질소 액체에서 급속히 냉동시키고(snap frozen) -80℃에서 저장하였다. 나머지 절반을 후속적인 파라핀 포매(embedding) 및 조직 분석(histology)을 위해 4% 포르말린에 고정시켰다.
조직 분석
4% 포르말린에 고정된 폐 조직을 파라핀에 포매시키고 이크로톰(icrotome)(Leica SM200R)을 사용하여 5 ㎛로 자르고 폴리-L-라이신 코팅된 슬라이드에 놓았다. 이후 상기 부분을 슬라이드에서 건조시키고(60℃에서 2 시간) 실온에서 냉각되도록 두었다. 콜라겐 축적을 메이슨 트리크롬 염색(Masson's Trichrome staining)을 사용하여 평가하였다.
결과
도 1A는 대조 그룹에서 수득된 결과를 나타내고, 이는 블레오마이신의 기관내 투여를 대신하여 식염수와 비이클을 수용한 것이다.
블레오마이신과 비이클이 기관내 투입된 래트에서 도 1B에 나타난 바와 같이 심각한 폐 섬유증이 발생되었다. 폐포가 주로 섬유모세포에 의해 대체되었고 세포외 기질 및 통상의 폐 구조가 거의 없어졌다.
50mg/kg의 실시예 A(화합물 (m))로 블레오마이신-처리된 래트의 일일 치료는 상기 모델에서 지속적이고, 거의 완전한 폐 섬유증의 회복을 나타내었다. 전형적인 예가 도 1C에 나타나있다. 폐포는 손상되지 않고 섬유모세포 침윤 또는 세포외 기질 축적이 거의 일어나지 않는다. 통상의 폐 구조가 유지되고, 이는 도 1C와 도 1A의 비교에 의해 증명된다.
(B) 대표적인 화합물의 블레오마이신 유발 폐 섬유증에 따른 섬유성 마커 유전자의 발현에 대한 영향
mRNA 추출 및 cDNA의 합성
유전자 발현의 조사를 위한 냉동된 폐 조직의 한 부분을 무균 메스 칼날(scalpel blade)를 사용하여 작은 조각으로 잘랐다. 이후 약 100mg의 조직을 2ml의 에펜도르프 튜브에 넣고 1.5ml의 Trizol(Invitrogen)을 첨가하였다. 이후 무균 텅스텐 카바이드 비드(Qiagen)를 튜브에 첨가하고 튜브를 8분 동안 30.0 Hz로 Retsch MM300 조직 분쇄기(Qiagen)에 두었다. 상기 시간 경과 후, 비드를 제거하고 샘플을 12000rpm으로 10분 동안 원심분리하여 조직 조각을 제거하였다. RNA를 트리졸(Trizol)에 의해 공급된 변형된 버전의 제조자 프로토콜을 사용하여 추출하였다. 잠시동안, 0.3ml 클로로포름을 튜브에 첨가하고 튜브를 세게 흔들고 실온에서 5분 동안 배양하고, 튜브를 15분 동안 12000rpm으로 4℃에서 원심분리 하였다. 이어서 상층의 투명한 수성상을 모으고 750㎕ 이소프로판올에 첨가하였다. 이후 이를 세게 흔들고 -80℃에서 밤새 저장하였다. 이어서 상기 샘플을 실온에서 15분 동안 배양하고, 이를 40분 동안 12000rpm으로 4℃에서 원심분리하였다. 이후 상청액을 제거하고 500㎕의 70% 에탄올을 첨가하여 펠렛(pellet)을 세척하고 샘플을 10분 동안 12000rpm으로 4℃에서 원심분리 하고, 이러한 세척 과정을 2회 반복하고, 펠렛을 10 -15 분 동안 건조되도록 두었다. 마지막으로 펠렛을 RNase가 없는 물 20㎕에 다시 현탁시키고 -80℃에서 저장하였다. 각각의 샘플의 농도를 분광 광도계를 사용하여 측정하였다.
Superscript™III(Invitrogen, Paisley, UK) RT-제1 스트랜드 합성 키트를 사용하여, 2㎍의 각각의 mRNA 샘플을 생산자 프로토콜의 변형된 버전(modified version of the manufacturer's protocol)을 사용하여 역전사시켰다. 잠시동안, 2 ㎍ RNA, 1㎕ 랜덤 헥사머 프라이머(50ng/㎕), 1㎕ dNTP 믹스(10mM)의 혼합물을 DEPC-처리된 물로 10㎕가 되게 하고 5분 동안 65℃에서 배양하고, 5분 동안 얼음 위에 두었다. 이에 이어서, 각각의 반응에, 2㎕ RT 버퍼(10X), 4㎕ MgCl2(25 mM), 2㎕ DTT(0.1M), 1㎕ RNaseOUT™(400U/㎕) 및 1㎕ SuperScript™III 효소(200U/㎕)를 첨가하고 혼합물을 25℃에서 10분 동안, 50℃에서 50분 동안 및 85℃에서 5분 동안 열 순환기(Applied Biosystems)에 두었고, 1㎕의 RNase H를 첨가하고 37℃에서 20분 동안 배양하였다. RT 반응이 모든 mRNA를 cDNA로 전사시켰고 농도가 100ng/㎕라는 가정을 사용하여 합성된 cDNA를 5ng/㎕로 희석시켰다.
실시간 PCR을 사용한 유전자 발현의 조사
유전자 발현을 각각의 샘플에서 어플라이드 바이오시스템즈(Applied Biosystems) 7700 서열 분석 시스템을 사용하여 조사하였다. 18S 내부 조절을 위한 프라이머(primer)를 미리 제조된 분석 시약 키트로 구매한 반면, 여기서 프로-콜라겐 I 및 피브로넥틴에 대한 프라이머 및 프로브(probe)(하기 표 2 참조)를 PrimerExpress™(Applied Biosystems)를 사용하여 설계하였고, 이 때 각각의 세트에서 적어도 하나의 프라이머 또는 프로브가 인트론/엑손 접합(intron/exon junction)과 겹쳐서 cDNA 샘플의 임의의 오염 게놈 DNA의 증폭 가능성을 제거하도록 하였다. 구입된 PDAR은 또한 cDNA만을 증폭시켰다.
표적 | 서열 | |
피브로넥틴 | 정방향 | 5'-GAT GCC GAT CAG AAG TTT GGA-3' |
역방향 | 5'-TCG TTG GTC GTG CAG ATC TC-3' | |
프로브 | 5'-FAM-CTG CCC AAT GGC TGC CCA TGA-TAMRA-3' | |
프로-콜라겐 I | 정방향 | 5'-CAG ACT GGC AAC CTG AAG AAG TC-3' |
역방향 | 5'-TCG CCC CTG AGC TCG AT-3' | |
프로브 | 5'-FAM-CTG CTC CTC CAG GGC TCC AAC GA-TAMRA3' |
실시간 PCR을 25㎕의 반응물에서, 반응당 25 ng(5㎕)의 cDNA를 사용하여 수행하였다. 정량적 PCR 코어 키트를 구매하였고(Eurogentec) 마스터-믹스(master-mix)를 다음과 같이 100회의 반응에서 보충하였다: 500㎕ 10X 반응 완충액, 500㎕ MgCl2(50mM), 200㎕ dNTP 혼합 용액(5mM), 25㎕ 핫 골드스타(Hot Goldstar) 효소, 75㎕ 18S PDAR, 22.5㎕ 정방향 프라이머, 22.5㎕ 역방향 프라이머, 15㎕ 프로브 및 640㎕ DEPC 처리된 물. 이어서 상기 마스터-믹스의 20㎕를 25ng(5㎕) 표적 cDNA에 첨가하였다. 각각의 분석을 3회 반복하였다.
유전자 발현을 정량하기 위해서, 각각의 프라이머 세트에 대해 표준 곡선을 만들었고 각각의 플레이트에 포함시켰다. 표준은 조사되는 모든 cDNA의 혼합물로 이루어졌다. 이러한 cDNA의 혼합물을 연속적으로 10, 20, 50, 100, 100회 희석시켰다. 표준 곡선을 희석 인자의 LOG10에 대한 수득된 CT(Cycle at which amplification reaches a set Threshold)로 구성하였다. 곡선을 표적 유전자 및 18S rRNA 내부 조절에 대해 그렸다. 이어서 각각의 샘플의 두 가지 표적 모두에 대한 CT값을 표준 곡선을 이용하여 폴드 딜루션(fold dilution)으로 전환하였고 표적 유전자를 18S 유전자 값으로 표준화하였다.
통계
모든 통계적 분석을 GraphPad Prism V 4.02 소프트웨어를 사용하여 수행하였다. 비모수 T-검정(Mann-Whitney U 검정)을 사용하여 비교하였고 유의값(significant value)은 p = 0.05이었다.
결과
결과를 도 2(프로콜라겐 I) 및 3(피브로넥틴)에 나타내었다. 각각의 데이터 포인트는 래트 한 마리의 폐로부터 분리된 RNA를 나타낸다.
블레오마이신의 기관 내 투여 및 비이클의 후속적인 처리는 폐의 프로콜라겐 I의 증가를 보였고, 피브로넥틴 유전자 발현은, 도 2 및 3에 보이는 바와 같이, 도 1B에 보이는 조직학적으로 명백한 폐 섬유증과 일치한다.
50mg/kg의 실시예 A (화합물 (m))로 처리된 블레오마이신 처리된 래트의 일일 치료는 도 2 및 3에 보이는 바와 같이, 상기 모델에서 섬유성 마커 유전자 발현의 상당한 (p ≤ 0.0001) 억제를 나타내었다.
따라서 상기 실험은 섬유성 마커의 발현, 및 이에 따른 세포외 기질의 축적이 실시예 A(화합물 (m))의 처리에 의해 급격하게 감소될 수 있다는 것을 증명한다.
실시예 B2:
실시예 B2의 다음의 실험에서, 화합물 목록의 화합물 (u)인 3-Z-[1-(4-(N-((4-메틸-피페라진-1-일)-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논을 사용하였다.
모든 사용된 방법은 실시예 B1의 실험에 기재된 방법과 동일하지만, 화합물 (m) 대신 화합물 (u)를 사용하였다.
(A) 블레오마이신 유발 폐 섬유증에 따른 폐 손상에 대한 대표적인 화합물의 영향
시료를 상기 실험 실시예 B1(A)의 표 1에 기재된 바와 같이 처리한 랫트로부터 제조하였다.
결과
도 4A는 대조 그룹에서 수득된 결과를 나타내고, 이는 블레오마이신의 기관내 투여를 대신하여 식염수와 비이클을 수용한 것이다.
블레오마이신과 비이클이 기관내 투입된 래트에서 도 4B에 나타난 바와 같이 심각한 폐 섬유증이 발생되었다. 폐포가 주로 섬유모세포에 의해 대체되었고 세포외 기질 및 통상의 폐 구조가 거의 없어졌다.
50mg/kg의 화합물 (u)로 블레오마이신-처리된 래트의 일일 치료는 상기 모델에서 지속적이고, 거의 완전한 폐 섬유증의 회복을 나타내었다. 전형적인 예가 도 4C에 나타나있다. 폐포는 손상되지 않고 섬유모세포 침윤 또는 세포외 기질 축적이 거의 일어나지 않는다. 통상의 폐 구조가 유지되고, 이는 도 4C와 도 4A의 비교에 의해 증명된다.
(B) 대표적인 화합물의 블레오마이신 유발 폐 섬유증에 따른 섬유성 마커 유전자의 발현에 대한 영향
실험을 상기 실시예 B1(B)에 기재된 방법을 사용하여 수행하였다.
결과를 도 5(프로콜라겐 I) 및 6(TGFb)에 나타내었다. 각각의 데이터 포인트는 래트 한 마리의 폐로부터 분리된 RNA를 나타낸다.
블레오마이신의 기관 내 투여 및 비이클의 후속적인 처리는 폐의 프로콜라겐 I의 증가를 보였고, TGFb 유전자 발현은, 도 2 및 3에 보이는 바와 같이, 도 5 및 6에 보이는 조직학적으로 명백한 폐 섬유증과 일치한다.
50mg/kg의 화합물 (u)로 처리된 블레오마이신 처리된 래트의 일일 치료는 도 2 및 3에 보이는 바와 같이, 상기 모델에서 섬유성 마커 유전자 발현의 상당한 (p ≤ 0.0001) 억제를 나타내었다.
따라서 상기 실험은 또한 섬유성 마커의 발현, 및 이에 따른 세포외 기질의 축적이 본 발명의 또 다른 대표 화합물, 즉 화합물 (u)의 처리에 의해 급격하게 감소될 수 있다는 것을 증명한다.
본 발명에 따른 화합물은 이의 생물학적 특성 때문에 단독 요법으로 또는 다른 약제학적으로 활성인 화합물과 함께 사용될 수 있다. 이러한 약제학적으로 활성인 화합물은 예를 들어, 섬유증의 치료에서도 약제학적으로 활성일 수 있다. 이러한 약제학적으로 활성인 화합물은 또한 점액용해성(secretolytic), 기관지용해성(broncholytic) 및/또는 항염증성 활성을 갖는 물질일 수 있다.
본 발명에 따른 바람직한 양태에서, 이러한 약제학적으로 활성인 화합물은 바람직하게는 항콜린제, 베타-2 미메틱, 스테로이드, PDE-IV 억제제, p38 MAP 키나제 억제제, NK1 길항제, LTD4 길항제, EGFR 억제제 및 엔도텔린-길항제로 이루어진 그룹으로부터 선택된다.
항콜린제는 바람직하게는 티오트로피움 염, 옥시트로피움 염, 플루트로피움 염, 이프라트로피움 염, 글리코피로늄 염 및 트로스피움 염으로 이루어진 그룹으로부터 선택될 수 있다.
베타-2 미메틱은 바람직하게는 예를 들어, 본원에 참조로서 인용된, US 4,460,581에 기재된 베타-2 미메틱으로부터 선택될 수 있다.
PDE-IV 억제제는 바람직하게는 엔프로필린(enprofyllin), 테오필린(theophyllin), 로플루미라스트(roflumilast), 아리플로(ariflo)(cilomilast), CP-325,366, BY343, D-4396 (Sch-351591), AWD-12-281 (Gω-842470), N-(3,5-디클로로-1-옥소-피리딘-4-일)-4-디플루오로메톡시-3-사이클로프로필메톡시벤즈아미드, NCS-613, 푸마펜틴(pumafentine), (-)p-[(4aR*,10bS*)-9-에톡시-1,2,3,4,4a,10b-헥사하이드로-8-메톡시-2-메틸벤조[s][1,6]나프티리딘-6-일]-N,N-디이소프로필벤즈아미드, (R)-(+)-1-(4-브로모벤질)-4-[(3-사이클로펜틸옥시)-4-메톡시페닐]-2-피롤리돈, 3-(사이클로펜틸옥시-4-메톡시페닐)-1-(4-N'-[N-2-시아노-S-메틸-이소티오우레이도]벤질)-2-피롤리돈, 시스[4-시아노-4-(3-사이클로펜틸옥시-4-메톡시페닐)사이클로헥산-1-카본산], 2-카보메톡시-4-시아노-4-(3-사이클로프로필메톡시-4-디플루오로메톡시페닐)사이클로헥산-1-온, 시스[4-시아노-4-(3-사이클로프로필메톡시-4-디플루오로메톡시페닐)사이클로헥산-1-올], (R)-(+)-에틸[4-(3-사이클로펜틸옥시-4-메톡시페닐)피롤리딘-2-일리덴]아세테이트, (S)-(-)-에틸[4-(3-사이클로펜틸옥시-4-메톡시페닐)피롤리딘-2-일리덴]아세테이트, CDP840, Bay-198004, D-4418, PD-168787, T-440, T-2585, 아로필린(arofyllin), 아티조람(atizoram), V-11294A, Cl-1018, CDC-801, CDC-3052, D-22888, YM-58997, Z-15370, 9-사이클로펜틸-5,6-디하이드로-7-에틸-3-(2-티에닐)-9H-피라졸로[3,4-c]-1,2,4-트리아졸로[4,3-a]피리딘 및 9-사이클로펜틸-5,6-디하이드로-7-에틸-3-(3급-부틸)-9H-피라졸로[3,4-c]-1,2,4-트리아졸로[4,3-a]피리딘으로 이루어진 그룹으로부터 선택될 수 있다. 이러한 화합물은 가능한 경우, 이의 라세미체, 에난티오머 또는 디아스테레오머의 형태, 또는 이의 약제학적으로 허용되는 산 부가 염의 형태, 또는 이의 용매화물 및/또는 수화물의 형태로 존재할 수 있다.
스테로이드는 바람직하게는 프레드니솔론(prednisolone), 프레드니손(prednisone), 부틱소코르트프로피오네이트(butixocortpropionate), RPR-106541, 플루니솔리드(flunisolid), 베클로메타존(beclomethasone), 트리암시놀론(triamcinolone), 부데소니드(budesonid), 플루티카존(fluticasone), 모메타존(mometasone), 시클레소니드(ciclesonid), 로플레포니드(rofleponid), ST-126, 덱사메타존(dexamethasone), 6α,9α-디플루오로-17α-[(2-퓨라닐카보닐)옥시]-11β-하이드록시-16α-메틸-3-옥소-안드로스타-1,4-디엔-17β-카보티온산 (S)-플루오로메틸에스테르 및 6α,9α-디플루오로-11β-하이드록시-16α-메틸-3-옥소-17α-프로피오닐옥시-안드로스타-1,4-디엔-17β-카보티온산 (S)-(2-옥소-테트라하이드로-퓨란-3S-일)에스테르로 이루어진 그룹으로부터 선택될 수 있다. 이들 화합물은, 가능한 경우, 이의 라세미체, 에난티오머 또는 디아스테레오머의 형태, 또는 이의 약제학적으로 허용되는 산 부가 염의 형태, 또는 이의 용매화물 및/또는 수화물의 형태로 사용될 수 있다.
p38 MAP 키나제 억제제는 바람직하게는 예를 들어 미국 특허 US 5,716,972, US 5,686,455, US 5,656,644, US 5,593,992, US 5,593,991, US 5,663,334, US 5,670,527, US 5,559,137, 5,658,903, US 5,739,143, US 5,756,499, US 6,277,989, US 6,340,685, 및 US 5,716,955 및 PCT 출원 WO 92/12154, WO 94/19350, WO 95/09853, WO 95/09851, WO 95/09847, WO 95/09852, WO 97/25048, WO 97/25047, WO 97/33883, WO 97/35856, WO 97/35855, WO 97/36587, WO 97/47618, WO 97/16442, WO 97/16441, WO 97/12876, WO 98/25619, WO 98/06715, WO 98/07425, WO 98/28292, WO 98/56377, WO 98/07966, WO 98/56377, WO 98/22109, WO 98/24782, WO 98/24780, WO 98/22457, WO 98/52558, WO 98/52559, WO 98/52941, WO 98/52937, WO 98/52940, WO 98/56788, WO 98/27098, WO 98/47892, WO 98/47899, WO 98/50356, WO 98/32733, WO 99/58523, WO 99/01452, WO 99/01131, WO 99/01130, WO 99/01136, WO 99/17776, WO 99/32121, WO 99/58502, WO 99/58523, WO 99/57101, WO 99/61426, WO 99/59960, WO 99/59959, WO 99/00357, WO 99/03837, WO 99/01441, WO 99/01449, WO 99/03484, WO 99/15164, WO 99/32110, WO 99/32111, WO 99/32463, WO 99/64400, WO 99/43680, WO 99/17204, WO 99/25717, WO 99/50238, WO 99/61437, WO 99/61440, WO 00/26209, WO 00/18738, WO 00/17175, WO 00/20402, WO 00/01688, WO 00/07980, WO 00/07991, WO 00/06563, WO 00/12074, WO 00/12497, WO 00/31072, WO 00/31063, WO 00/23072, WO 00/31065, WO 00/35911, WO 00/39116, WO 00/43384, WO 00/41698, WO 00/69848, WO 00/26209, WO 00/63204, WO 00/07985, WO 00/59904, WO 00/71535, WO 00/10563, WO 00/25791, WO 00/55152, WO 00/55139, WO 00/17204, WO 00/36096, WO 00/55120, WO 00/55153, WO 00/56738, WO 01/21591, WO 01/29041, WO 01/29042, WO 01/62731, WO 01/05744, WO 01/05745, WO 01/05746, WO 01/05749, WO 01/05751, WO 01/27315, WO 01/42189, WO 01/00208, WO 01/42241, WO 01/34605, WO 01/47897, WO 01/64676, WO 01/37837, WO 01/38312, WO 01/38313, WO 01/36403, WO 01/38314, WO 01/47921, WO 01/27089, DE 19842833, 및 JP 2000 86657에 기재된 p38 키나제 억제제로 이루어진 그룹으로부터 선택될 수 있고, 이들 문헌은 모두 전체가 본원에 참조로서 인용된다. 본 발명에 따른 배합물 중 특히 관심 대상은 US 6,277,989, US 6,340,685, WO 00/12074, WO 00/12497, WO 00/59904, WO 00/71535, WO 01/64676, WO 99/61426, WO 00/10563, WO 00/25791, WO 01/37837, WO 01/38312, WO 01/38313, WO 01/38314, WO 01/47921, WO 99/61437, WO 99/61440, WO 00/17175, WO 00/17204, WO 00/36096, WO 98/27098, WO 99/00357, WO 99/58502, WO 99/64400, WO 99/01131, WO 00/43384, WO 00/55152, WO 00/55139 및 WO 01/36403에 기재된 p38 억제제이다. 바람직한 양태에서 p38 키나제 억제제는 WO 99/01131에 기재된 바와 같이 하기 화학식 I의 화합물 또는 이의 약제학적으로 허용되는 염으로부터 선택된다.
화학식 I
상기 화학식 I에서
R1은 4-피리딜, 피리미디닐, 4-피리다지닐, 1,2,4-트리아진-5-일, 퀴놀릴, 이소퀴놀리닐 또는 퀴나졸린-4-일 환이고, 상기 환은 Y-Ra로, 또한 C1-4 알킬, 할로겐, 하이드록실, C1-4 알콕시, C1-4 알킬티오, C1-4 알킬설피닐, CH2OR12, 아미노, 모노 및 디- C1-6 알킬 치환된 아미노, N-헤테로사이클릴 환(환은 5 내지 7개의 원자를 갖고 산소, 황 또는 NR15 로부터 선택된 추가의 이종원자를 임의로 함유한다), N(R10)C(O)Rb 또는 NHRa로부터 선택된 추가의 독립적인 치환체로 임의로 치환되고,
Y는 산소 또는 황이고;
R4는 페닐, 나프트-1-일 또는 나프틸, 또는 헤테로아릴이고, 이는 1 또는 2개의 치환체에 의해 임의로 치환되고, 이들 각각은 독립적으로 선택되고, 이는 4-페닐, 4-나프트-1-일, 5-나프트-2-일 또는 6-나프트-2-일 치환체에 대해서는, 할로겐, 시아노, 니트로, C(Z)NR7R17, C(Z)OR16, (CR10R20)vCOR12, SR5, SOR5, OR12, 할로-치환된-C1-4 알킬, C1-4 알킬, ZC(Z)R12, NR10C(Z)R16 또는 (CR10R20)vNR10R20 이고, 다른 위치의 치환체에 대해서는 할로겐, 시아노, C(Z)NR13R14, C(Z)OR3, (CR10R20)m''COR3, S(O)mR3, OR3, 할로-치환된-C1-4 알킬, C1-4 알킬, (CR10R20)m''R10C(Z)R3, NR10S(O)m'R8, NR10S(O)m'NR7R17, ZC(Z)R3 또는 (CR10R20)m''NR13R14이고;
Z는 산소 또는 황이고;
n은 정수 1 내지 10이고;
m은 0, 또는 정수 1 또는 2이고;
m'는 정수 1 또는 2이고;
m"는 0, 또는 정수 1 내지 5이고;
v는 0, 또는 정수 1 내지 2이고;
R2는 -C(H) (A) (R22)이고;
A는 임의로 치환된 아릴, 헤테로사이클릴 또는 헤테로아릴 환이고, 또는 A는 치환된 C1-10알킬이고;
R22는 임의로 치환된 C1-10 알킬이고;
Ra는 아릴, 아릴 C1-6 알킬, 헤테로사이클릭, 헤테로사이클릴 C1-6 알킬, 헤테로아릴, 헤테로아릴C1-6알킬이고, 여기서 이들 잔기 각각은 임의로 치환될 수 있고;
Rb는 수소, C1-6 알킬, C3-7 사이클로알킬, 아릴, 아릴 C1-4 알킬, 헤테로아릴, 헤테로아릴C1-4 알킬, 헤테로사이클릴 또는 헤테로사이클릴C1-4 알킬이고, 여기서 이들 잔기 각각은 임의로 치환될 수 있고;
R3는 헤테로사이클릴, 헤테로사이클릴 C1-10 알킬 또는 R8이고;
R5는 수소, C1-4 알킬, C2-4 알케닐, C2-4 알키닐 또는 NR7R17이고, 잔기 SR5는 SNR7R17가 아니고 SOR5는 SOH가 아니고;
R6는 수소, 약제학적으로 허용되는 양이온, C1-10 알킬, C3-7 사이클로알킬, 아릴, 아릴 C1-4 알킬, 헤테로아릴, 헤테로아릴 C1-4 알킬, 헤테로사이클릴, 아릴, 또는 C1-10 알카노일이고;
R7 및 R17는 각각 수소 또는 C1-4 알킬로부터 독립적으로 선택되거나 R7 및 R17는 이들이 결합한 질소와 함께 5 내지 7원 헤테로사이클릭 환을 형성하고 상기 환은 산소, 황 또는 NR15로부터 선택된 추가의 이종원자를 임의로 함유하고;
R8는 C1-10 알킬, 할로-치환된 C1-10 알킬, C2-10 알케닐, C2-10 알키닐, C3-7 사이클로알킬, C5-7 사이클로알케닐, 아릴, 아릴 C1-10 알킬, 헤테로아릴, 헤테로아릴 C1-10 알킬, (CR10R20)nOR11, (CR10R20)nS(O)mR18, (CR10R20)nNHS(O)2R18, (CR10R20)nNR13R14이고, 여기서 아릴, 아릴알킬, 헤테로아릴, 헤테로아릴 알킬은 임의로 치환될 수 있고;
R9는 수소, C(Z) R11 또는 임의로 치환된 C1-10 알킬, S(O)2R18, 임의로 치환된 아릴 또는 임의로 치환된 아릴 C1-4 알킬이고;
R10 및 R20는 각각 독립적으로 수소 또는 C1-4 알킬로부터 선택되고;
R11는 수소, C1-10 알킬, C3-7 사이클로알킬, 헤테로사이클릴, 헤테로사이클릴 C1-10 알킬, 아릴, 아릴C1-10 알킬, 헤테로아릴 또는 헤테로아릴 C1-10 알킬이고, 여기서 이들 잔기는 임의로 치환될 수 있고;
R12는 수소 또는 R16이고;
R13 및 R14는 각각 수소 또는 임의로 치환된 C1-4 알킬, 임의로 치환된 아릴 또는 임의로 치환된 아릴C1-4 알킬로부터 독립적으로 선택되거나, 이들이 결합한 질소와 함께 5 내지 7원 헤테로사이클릭 환을 형성하고, 상기 환은 산소, 황 또는 NR9로부터 선택된 추가의 이종 원자를 임의로 함유하고;
R15는 R10 또는 C(Z)-C1-4 알킬이고;
R16은 C1-4 알킬, 할로-치환된-C1-4 알킬 또는 C3-7 사이클로알킬이고;
R18은 C1-10 알킬, C3-7 사이클로알킬, 헤테로사이클릴, 아릴, 아릴1-10 알킬, 헤테로사이클릴, 헤테로사이클릴- C1-10알킬, 헤테로아릴 또는 헤테로아릴1-10알킬이다.
NK1 길항제는 바람직하게는 N-[2-(3,5-비스-트리플루오로메틸-페닐)-에틸]-2-{4-사이클로프로필메틸-피페라진-1-일}-N-메틸-2-페닐-아세트아미드(BIIF 1149), CP-122721, FK-888, NKP 608C, NKP 608A, CGP 60829, SR 48968(Saredutant), SR 140333(놀피탄튬 베실레이트/클로라이드), LY 303 870(Lanepitant), MEN-11420 (Nepadutant), SB 223412, MDL-105172A, MDL-103896, MEN-11149, MEN-11467, DNK 333A, SR-144190, YM-49244, YM-44778, ZM-274773, MEN-10930, S-19752, Neuronorm, YM-35375, DA-5018, 아프레피탄트(Aprepitant)(MK-869), L-754030, CJ-11974, L-758298, DNK-33A, 6b-I, CJ-11974, TAK-637, GR 205171 및 화학식 VIII의 아릴글리신 아미드 유도체로 이루어진 그룹으로부터 선택되고
상기 화학식 VIII에서
R1 및 R2 는 이들이 결합된 질소 원자와 함께 화학식
의 환을 형성하고 또는,
여기서 r 및 s는 독립적으로 2 또는 3을 나타내고;
R6는 H, -C1-C5-알킬, C3-C5-알케닐, 프로피닐, 하이드록시(C2-C4)알킬, 메톡시(C2-C4)알킬, 디(C1-C3)알킬아미노(C2-C4)알킬, 아미노(C2-C4)알킬, 아미노, 디(C1-C3)알킬아미노, 모노플루오로- 내지 퍼플루오로(C1-C2)알킬, N-메틸피페리디닐, 피리딜, 피리미디닐, 피라지닐 또는 피리다지닐이고,
R7은 (a) 내지 (b)에 의해 정의된 임의의 그룹을 나타내고:
(a) 하이드록시,
(b) 4-피페리디노피페리딜,
(c)
여기서 R16 및 R17는 독립적으로 H, (C1-C4)알킬, (C3-C6)사이클로알킬, 하이드록시(C2-C4)알킬, 디하이드록시(C2-C4)알킬, (C1-C3)알콕시(C2-C4)알킬, 페닐(C1-C4)알킬 또는 디(C1-C3)알킬아미노(C2-C4)알킬을 나타내고,
R8는 H를 나타내고,
임의로 에난티오머, 에난티오머의 혼합물 또는 라세미체의 형태이다.
상술한 화학식 VIII의 화합물은 WO 96/32386, WO 97/32865 및 WO 02/32865에 기재되어 있다. 이러한 국제특허출원의 문헌은 전체가 본원에서 참조로서 인용되었다.
LTD4 길항제는 바람직하게는 몬테루카스트(montelukast), 1-(((R)-(3-(2-(6,7-디플루오로-2-퀴놀리닐)에테닐)페닐)-3-(2-(2- 하이드록시-2-프로필)페닐)티오)메틸사이클로프로판-아세테이트, 1-(((1(R)-3(3-(2-(2,3-디클로로티에노[3,2-b]피리딘-5-일)-(E)-에테닐)페닐)-3-(2-(1-하이드록시-1-메틸에틸)페닐)프로필)티오)메틸)사이클로프로판-아세테이트, 프란루카스트(pranlukast), 자피르루카스 트(zafirlukast), 2-[[2-(4-3급-부틸-2-티아졸릴)-5-벤조퓨라닐]옥시메틸]페닐]아세테이트, MCC-847 (ZD-3523), MN-001, MEN-91507 (LM-1507), VUF-5078, VUF-K-8707 및 L-733321로 이루어진 그룹으로부터 선택될 수 있다. 이들 화합물은 가능한 경우, 이의 라세미체, 에난티오머 또는 디아스테레오머의 형태로, 또는 약제학적으로 허용되는 이의 산 부가 염의 형태, 또는 이의 용매화물 및/또는 수화물의 형태로 사용될 수 있다.
EGFR 억제제는 바람직하게는 4-[(3-클로르-4-플루오르페닐)아미노]-6-{[4-(모르폴린-4-일)-1-옥소-2-부텐-1-일]-아미노}-7-사이클로프로필메톡시-키나졸린, 4-[(3-클로르-4-플루오르페닐)아미노]-6-{[4-(N,N-디에틸아미노)-1-옥소-2-부텐-1-일]-아미노}-7-이클로프로필메톡시-키나졸린, 4-[(3-클로르-4-플루오르페닐)아미노]-6-{[4-(N,N-디메틸아미노)-1-옥소-2-부텐-1-일]아미노}-7-사이클로프로필메톡시-키나졸린, 4-[(R)-(1-페닐-에틸)아미노]-6-{[4-(모르폴린-4-일)-1-옥소-2-부텐-1-일]-아미노}-7-사이클로펜틸옥시-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-{[4-((R)-6-메틸-2-옥소-모르폴린-4-일)-1-옥소-2-부텐-1-일]아미노}-7-사이클로프로필메톡시-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-{[4-((R)-6-메틸-2-옥소-모르폴린-4-일)-1-옥소-2-부텐-1-일]아미노}-7-[(S)-(테트라하이드로퓨란-3-일)옥시]-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-{[4-((R)-2-메톡시메틸-6-옥소-모르폴린-4-일)-1-옥소-2-부텐-1-일]아미노}-7-사이클로프로필메톡시-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-[2-((S)-6-메틸-2-옥소-모르폴린-4-일)-에톡시]-7-메톡시-키나졸린, 4-[(3-클로르-4-플루오르페닐)아미 노]-6-({4-[N-(2-메톡시-에틸)-N-메틸-아미노]-1-옥소-2-부텐-1-일}아미노)-7-사이클로프로필메톡시-키나졸린, 4-[(3-클로르-4-플루오르페닐)아미노]-6-{[4-(N,N-디메틸아미노)-1-옥소-2-부텐-1-일]아미노}-7-사이클로펜틸옥시-키나졸린, 4-[(R)-(1-페닐-에틸)아미노]-6-{[4-(N,N-비스-(2-메톡시-에틸)-아미노)-1-옥소-2-부텐-1-일]아미노}-7-사이클로프로필메톡시-키나졸린, 4-[(R)-(1-페닐-에틸)아미노]-6-({4-[N-(2-메톡시-에틸)-N-에틸-아미노]-1-옥소-2-부텐-1-일}아미노)-7-사이클로프로필메톡시-키나졸린, 4-[(R)-(1-페닐-에틸)아미노]-6-({4-[N-(2-메톡시-에틸)-N-메틸-아미노]-1-옥소-2-부텐-1-일}아미노)-7-사이클로프로필메톡시-키나졸린, 4-[(R)-(1-페닐-에틸)아미노]-6-({4-[N-(테트라하이드로피란-4-일)-N-메틸-아미노]-1-옥소-2-부텐-1-일}아미노)-7-사이클로프로필메톡시-키나졸린, 4-[(3-클로르-4-플루오르페닐)아미노]-6-{[4-(N,N-디메틸아미노)-1-옥소-2-부텐-1-일]아미노}-7-((R)-테트라하이드로퓨란-3-일옥시)-키나졸린, 4-[(3-클로르-4-플루오르페닐)아미노]-6-{[4-(N,N-디메틸아미노)-1-옥소-2-부텐-1-일]아미노}-7-((S)-테트라하이드로퓨란-3-일옥시)-키나졸린, 4-[(3-클로르-4-플루오르페닐)아미노]-6-({4-[N-(2-메톡시-에틸)-N-메틸-아미노]-1-옥소-2-부텐-1-일}아미노)-7-사이클로펜틸옥시-키나졸린, 4-[(3-클로르-4-플루오르페닐)아미노]-6-{[4-(N-사이클로프로필-N-메틸-아미노)-1-옥소-2-부텐-1-일]아미노}-7-사이클로펜틸옥시-키나졸린, 4-[(3-클로르-4-플루오르페닐)아미노]-6-{[4-(N,N-디메틸아미노)-1-옥소-2-부텐-1-일]아미노}-7-[(R)-(테트라하이드로퓨란-2-일)메톡시]-키나졸린, 4-[(3-클로르-4-플루오르페닐)아미노]-6-{[4-(N,N-디메틸아미노)-1-옥소-2-부텐-1-일]아미노}-7-[(S)-(테트라하 이드로퓨란-2-일)메톡시]-키나졸린, 4-[(3-에티닐-페닐)아미노]-6,7-비스-(2-메톡시-에톡시)-키나졸린, 4-[(3-클로르-4-플루오르페닐)아미노]-7-[3-(모르폴린-4-일)-프로필옥시]-6-[(비닐-카보닐)아미노]-키나졸린, 4-[(R)-(1-페닐-에틸)아미노]-6-(4-하이드록시-페닐)-7H-피롤로[2,3-d]피리미딘, 3-시아노-4-[(3-클로르-4-플루오르페닐)아미노]-6-{[4-(N,N-디메틸아미노)-1-옥소-2-부텐-1-일]아미노}-7-에톡시-키놀린, 4-{[3-클로르-4-(3-플루오르-벤질옥시)-페닐]아미노}-6-(5-{[(2-메탄설포닐-에틸)아미노]메틸}-퓨란-2-일)키나졸린, 4-[(R)-(1-페닐-에틸)아미노]-6-{[4-((R)-6-메틸-2-옥소-모르폴린-4-일)-1-옥소-2-부텐-1-일]아미노}-7-메톡시-키나졸린, 4-[(3-클로르-4-플루오르페닐)아미노]-6-{[4-(모르폴린-4-일)-1-옥소-2-부텐-1-일]-아미노}-7-[(테트라하이드로퓨란-2-일)메톡시]-키나졸린, 4-[(3-클로르-4-플루오르페닐)아미노]-6-({4-[N,N-비스-(2-메톡시-에틸)-아미노]-1-옥소-2-부텐-1-일}아미노)-7-[(테트라하이드로퓨란-2-일)메톡시]-키나졸린, 4-[(3-에티닐-페닐)아미노]-6-{[4-(5,5-디메틸-2-옥소-모르폴린-4-일)-1-옥소-2-부텐-1-일]아미노}-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-[2-(2,2-디메틸-6-옥소-모르폴린-4-일)-에톡시]-7-메톡시-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-[2-(2,2-디메틸-6-옥소-모르폴린-4-일)-에톡시]-7-[(R)-(테트라하이드로퓨란-2-일)메톡시]-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-7-[2-(2,2-디메틸-6-옥소-모르폴린-4-일)-에톡시]-6-[(S)-(테트라하이드로퓨란-2-일)메톡시]-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-{2-[4-(2-옥소-모르폴린-4-일)-피페리딘-1-일]-에톡시}-7-메톡시-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-[1-(3급 -부틸옥시카보닐)-피페리딘-4-일옥시]-7-메톡시-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-(트랜스-4-아미노-사이클로헥산-1-일옥시)-7-메톡시-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-(트랜스-4-메탄설포닐아미노-사이클로헥산-1-일옥시)-7-메톡시-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-(테트라하이드로피란-3-일옥시)-7-메톡시-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-(1-메틸-피페리딘-4-일옥시)-7-메톡시-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-{1-[(모르폴린-4-일)카보닐]-피페리딘-4-일-옥시}-7-메톡시-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-{1-[(메톡시메틸)카보닐]-피페리딘-4-일-옥시}-7-메톡시-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-(피페리딘-3-일옥시)-7-메톡시-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-[1-(2-아세틸아미노-에틸)-피페리딘-4-일옥시]-7-메톡시-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-(테트라하이드로피란-4-일옥시)-7-에톡시-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-((S)-테트라하이드로퓨란-3-일옥시)-7-하이드록시-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-(테트라하이드로피란-4-일옥시)-7-(2-메톡시-에톡시)-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-{트랜스-4-[(디메틸아미노)설포닐아미노]-사이클로헥산-1-일옥시}-7-메톡시-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-{트랜스-4-[(모르폴린-4-일)카보닐아미노]-사이클로헥산-1-일옥시}-7-메톡시-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-{트랜스-4-[(모르폴린-4-일)설포닐아미노]-사이클로헥산-1-일옥시}-7-메톡시-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-(테트라하이드로피란-4-일 옥시)-7-(2-아세틸아미노-에톡시)-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-(테트라하이드로피란-4-일옥시)-7-(2-메탄설포닐아미노-에톡시)-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-{1-[(피페리딘-1-일)카보닐]-피페리딘-4-일옥시}-7-메톡시-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-(1-아미노카보닐메틸-피페리딘-4-일옥시)-7-메톡시-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-(시스-4-{N-[(테트라하이드로피란-4-일)카보닐]-N-메틸-아미노}-사이클로헥산-1-일옥시)-7-메톡시-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-(시스-4-{N-[(모르폴린-4-일)카보닐]-N-메틸-아미노}-사이클로헥산-1-일옥시)-7-메톡시-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-(시스-4-{N-[(모르폴린-4-일)설포닐]-N-메틸-아미노}-사이클로헥산-1-일옥시)-7-메톡시-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-(트랜스-4-에탄설포닐아미노-사이클로헥산-1-일옥시)-7-메톡시-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-(1-메탄설포닐-피페리딘-4-일옥시)-7-에톡시-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-(1-메탄설포닐-피페리딘-4-일옥시)-7-(2-메톡시-에톡시)-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-[1-(2-메톡시-아세틸)-피페리딘-4-일옥시]-7-(2-메톡시-에톡시)-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-(시스-4-아세틸아미노-사이클로헥산-1-일옥시)-7-메톡시-키나졸린, 4-[(3-에티닐-페닐)아미노]-6-[1-(3급-부틸옥시카보닐)-피페리딘-4-일옥시]-7-메톡시-키나졸린, 4-[(3-에티닐-페닐)아미노]-6-(테트라하이드로피란-4-일옥시]-7-메톡시-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-(시스-4-{N-[(피페리딘-1-일)카보닐]-N-메틸-아미노}-사 이클로헥산-1-일옥시)-7-메톡시-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-(시스-4-{N-[(4-메틸-피페라진-1-일)카보닐]-N-메틸-아미노}-사이클로헥산-1-일옥시)-7-메톡시-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-{시스-4-[(모르폴린-4-일)카보닐아미노]-사이클로헥산-1-일옥시}-7-메톡시-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-{1-[2-(2-옥소피롤리딘-1-일)에틸]-피페리딘-4-일옥시}-7-메톡시-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-{1-[(모르폴린-4-일)카보닐]-피페리딘-4-일옥시}-7-(2-메톡시-에톡시)-키나졸린, 4-[(3-에티닐-페닐)아미노]-6-(1-아세틸-피페리딘-4-일옥시)-7-메톡시-키나졸린, 4-[(3-에티닐-페닐)아미노]-6-(1-메틸-피페리딘-4-일옥시)-7-메톡시-키나졸린, 4-[(3-에티닐-페닐)아미노]-6-(1-메탄설포닐-피페리딘-4-일옥시)-7-메톡시-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-(1-메틸-피페리딘-4-일옥시)-7(2-메톡시-에톡시)-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-(1-이소프로필옥시카보닐-피페리딘-4-일옥시)-7-메톡시-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-(시스-4-메틸아미노-사이클로헥산-1-일옥시)-7-메톡시-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-{시스-4-[N-(2-메톡시-아세틸)-N-메틸-아미노]-사이클로헥산-1-일옥시}-7-메톡시-키나졸린, 4-[(3-에티닐-페닐)아미노]-6-(피페리딘-4-일옥시)-7-메톡시-키나졸린, 4-[(3-에티닐-페닐)아미노]-6-[1-(2-메톡시-아세틸)-피페리딘-4-일옥시]-7-메톡시-키나졸린, 4-[(3-에티닐-페닐)아미노]-6-{1-[(모르폴린-4-일)카보닐]-피페리딘-4-일옥시}-7-메톡시-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-{1-[(시스-2,6-디메틸-모르폴린-4-일)카보닐]-피페리딘-4-일옥시}-7-메톡시- 키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-{1-[(2-메틸-모르폴린-4-일)카보닐]-피페리딘-4-일옥시}-7-메톡시-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-{1-[(S,S)-(2-옥사-5-아자-바이사이클로[2.2.1]헵트-5-일)카보닐]-피페리딘-4-일옥시}-7-메톡시-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-{1-[(N-메틸-N-2-메톡시에틸-아미노)카보닐]-피페리딘-4-일옥시}-7-메톡시-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-(1-에틸-피페리딘-4-일옥시)-7-메톡시-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-{1-[(2-메톡시에틸)카보닐]-피페리딘-4-일옥시}-7-메톡시-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-{1-[(3-메톡시프로필-아미노)-카보닐]-피페리딘-4-일옥시}-7-메톡시-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-[시스-4-(N-메탄설포닐-N-메틸-아미노)-사이클로헥산-1-일옥시]-7-메톡시-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-[시스-4-(N-아세틸-N-메틸-아미노)-사이클로헥산-1-일옥시]-7-메톡시-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-(트랜스-4-메틸아미노-사이클로헥산-1-일옥시)-7-메톡시-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-[트랜스-4-(N-메탄설포닐-N-메틸-아미노)-사이클로헥산-1-일옥시]-7-메톡시-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-(트랜스-4-디메틸아미노-사이클로헥산-1-일옥시)-7-메톡시-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-(트랜스-4-{N-[(모르폴린-4-일)카보닐]-N-메틸-아미노}-사이클로헥산-1-일옥시)-7-메톡시-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-[2-(2,2-디메틸-6-옥소-모르폴린-4-일)-에톡시]-7-[(S)-(테트라하이드로퓨란-2-일)메톡시]-키나졸린, 4-[(3-클로르-4-플루오르-페 닐)아미노]-6-(1-메탄설포닐-피페리딘-4-일옥시)-7-메톡시-키나졸린, 4-[(3-클로르-4-플루오르-페닐)아미노]-6-(1-시아노-피페리딘-4-일옥시)-7-메톡시-키나졸린, 세툭시맵(Cetuximab), 트라스투즈맵(Trastuzumab), ABX-EGF 및 Mab ICR-62로 이루어진 그룹으로부터 선택될 수 있다. 이들 화합물은 가능한 경우, 이의 라세미체, 에난티오머 또는 디아스테레오머의 형태로, 또는 약제학적으로 허용되는 이의 산 부가 염의 형태, 또는 이의 용매화물 및/또는 수화물의 형태로 사용될 수 있다. 이들 화합물은 종래 기술, 예를 들어 WO 96/30347, WO 97/02266, WO 99/35146, WO 00/31048, WO 00/78735, WO 01/34574, WO 01/61816, WO 01/77104, WO02/18351, WO 02/18372, WO 02/18373, WO 02/18376, WO 02/50043, WO 03/082290, Cancer Research 2004, 64:11 (3958-3965), Am J Health-Syst Pharm 2000, 57(15), 2063-2076, Clinical Therapeutics 1999, 21(2), 309-318, WO 98/50433 및 WO 95/20045에 기재되어 있다.
엔도텔린-길항제는 바람직하게는 테조센탄(tezosentan), 보센탄(bosentan), 엔라센탄(enrasentan), 식스타센탄(sixtasentan), T-0201, BMS-193884, K-8794, PD-156123, PD-156707, PD-160874, PD-180988, S-0139 및 ZD-1611로 이루어진 그룹으로부터 선택될 수 있다. 본 발명의 범주 내의 엔도텔린-길항제에 대한 임의의 참조는 염, 바람직하게는 약제학적으로 허용되는 산 부가 염, 또는 엔도텔린-길항제로부터 형성될 수 있는 유도체에 대한 참조를 포함한다.
이들 배합물은 동시에 또는 연속적으로 투여할 수 있다.
본 발명에 따른 화합물의 약제학적 용도는 바람직하게는 온혈 척추동물, 특 히사람에 대해, 체중 1kg 당 0.0001-100 mg의 용량으로 사용된다.
이들 화합물은 이들 자체로 또는 다른 활성 물질과 혼합되어 정맥내, 피하내, 근육내, 복막내 또는 비강 내 경로에 의해, 흡입에 의해, 또는 경피적으로, 또는 경구적으로 투여할 수 있지만, 특히 에어로졸 제형은 흡입에 적합하다.
투여를 위해 상기 제형은 하나 이상의 통상적인 비활성 고체, 반고체 또는 액체 담체, 예를 들어 전분, 서로 다른 유형의 셀룰로즈, 락토즈, 만니톨, 소르비톨, 글루코즈, 인산 칼슘, 경지방(hard fat), 지방산 알코올, 글리세롤, 중쇄 트리글리세라이드 및 관련 에스테르, 폴리에틸렌 글리콜, 정제된 특수유(specialty oils), 물, 물/에탄올, 물/글리세롤, 물/소르비톨, 물/폴리에틸렌 글리콜, 프로필렌 글리콜 및/또는 기능성 부형제, 예를 들어 폴리비닐-피롤리돈, 하이드록시프로필메틸셀룰로즈, 나트륨 카복시메틸-셀룰로즈, 나트륨 전분 글리콜레이트, 이산화규소, 폴리소르베이트, 폴리옥사머, 겔루사이어(gelucires), 스테아르산 마그네슘, 시트르산, 타르타르산 또는 이의 적합한 혼합물과 함께, 통상의 갈레닉(galenic) 조제, 예를 들어 보통(plain) 또는 코팅된 정제, 캡슐, 파우더, 주입가능한 용액, 앰플, 현탁액, 용액, 스프레이 또는 좌제로 제형화된다.
다음의 제형의 예는 본 발명의 범주를 제한하지 않으면서 본 발명을 설명한다.
실시예 F1: 75mg의 활성 물질을 함유하는 코팅된 정제
조성
정제 코어(core) 1개당 함유량:
활성 물질 75.0mg
인산 칼슘 131.0mg
폴리비닐피롤리돈 10.0mg
카복시메틸셀룰로즈 나트륨 10.0mg
이산화규소 2.5mg
스테아르산 마그네슘 1.5mg
230.0mg
조제 (직접 압축)
활성 물질을 모든 성분과 함께 혼합하고, 체질하고, 정제 제조 기계에서 압축시켜 목적하는 형태의 정제를 형성시킨다.
코어의 중량: 230mg
코어의 외형: 9mm, 양면이 볼록하다
이에따라 생산된 정제 코어를 하이드록시프로필메틸셀룰로즈로 필수적으로 이루어진 막으로 코팅한다.
코팅된 정제의 중량: 240mg.
실시예 F2: 100mg의 활성 물질을 함유하는 정제
조성
정제 1개의 함유량:
활성 물질 100.0mg
락토즈 80.0mg
옥수수 전분 34.0mg
하이드록시프로필메틸셀룰로즈 4.0mg
스테아르산 마그네슘 2.0mg
220.0mg
조제 (습윤 과립)
활성 물질, 락토즈 및 전분을 함께 혼합하고 하이드록시프로필메틸셀룰로즈 수용액으로 균일하게 적신다. 습윤 조성물을 거르고(2.0mm 메쉬 크기), 50℃에서 랙형(rack-type) 건조기에서 건조시킨 후, 이를 다시 거르고(1.5mm 메쉬 크기) 윤활제를 첨가한다. 완성된 혼합물을 압축시켜 정제를 형성한다.
정제의 중량: 220mg
정제의 외형: 10mm, 평평하고 한쪽면에 비스듬한 가장자리와 쪼개진 홈이 있다.
실시예 F3: 150mg의 활성 물질을 함유하는 정제
조성
정제 1개의 함유량:
활성 물질 150.0mg
락토즈 85.0mg
미정질 셀룰로즈 40.0mg
폴리비닐피롤리돈 10.0mg
이산화규소 10.0mg
스테아르산 마그네슘 5.0mg
300.0mg
조제 (건조 과립)
활성 물질을 락토즈, 폴리비닐-피롤리돈 및 미정질 셀룰로즈의 일부와 혼합하고, 스테아르산 마그네슘을, 예를 들어 롤러 압축기로 압축한다. 리본을 메쉬 크기가 0.8mm인 스크린을 통해 미세 미립으로 분쇄한다. 후속적으로 메쉬 크기가 0.5mm인 스크린을 통해 걸러내고 잔여 성분과 혼합한 후, 혼합물로부터 정제를 가압성형한다.
정제의 중량: 300mg
정제의 외형: 10mm, 평평하다
실시예 F4: 150mg의 활성 물질을 함유하는 경질 젤라틴 캡슐
조성
캡슐 1개의 함유량:
활성 물질 150.0mg
락토즈 85.0mg
미정질 셀룰로즈 40.0mg
폴리비닐피롤리돈 10.0mg
이산화규소 10.0mg
스테아르산 마그네슘 5.0mg
300.0mg
조제
활성 물질을 락토즈, 폴리비닐-피롤리돈 및 미정질 셀룰로즈의 일부와 혼합하고, 스테아르산 마그네슘를, 예를 들어 롤러 압축기로 압축한다. 리본을 메쉬 크기가 0.8mm인 스크린을 통해 미세 미립으로 분쇄한다. 후속적으로 메쉬 크기가 0.5mm인 스크린을 통해 걸러내고 잔여 성분과 혼합한 후, 완성된 혼합물을 크기1 의 경질 젤라틴 캡슐에 담는다.
캡슐 충전량: 약 300mg
캡슐 껍질: 크기 1의 경질 젤라틴 캡슐.
실시예 F5: 150mg의 활성 물질을 함유하는 좌제
좌제 1개의 함유량:
활성 물질 150.0mg
폴리에틸렌글리콜 1500 800.0mg
폴리에틸렌글리콜 6000 850.0mg
폴리옥실 40 수소화 피마자유 200.0mg
2,000.0mg
조제
좌제 덩어리가 용해된 후 활성 물질을 균질하게 그 안에 분배시키고 용해물을 냉각된 형틀로 붓는다.
실시예 F6: 50mg의 활성 물질을 함유하는 현탁액
100ml의 현탁액 함유량
활성 물질 1.00g
카복시메틸셀룰로즈 나트륨 0.10g
메틸 p-하이드록시벤조에이트 0.05g
프로필 p-하이드록시벤조에이트 0.01g
글루코즈 0.00g
글리세롤 5.00g
70% 소르비톨 용액 20.00g
향미제 0.30g
증류수를 100ml가 되도록 첨가한다.
조제
증류수를 70℃로 가열한다. 메틸 및 프로필 p-하이드록시벤조에이트를 글리세롤 및 카복시메틸셀룰로즈의 나트륨 염과 함께 그 안에 교반하면서 용해시킨다. 용액을 대기 온도로 냉각시키고 활성 물질을 첨가하고 그 안에 교반하면서 균질하 게 분산시킨다. 설탕, 소르비톨 용액 및 향미제가 첨가되고 용해된 후, 현탁액을 교반하면서 진공으로 하여 공기를 제거한다.
따라서, 5ml의 현탁액은 50mg의 활성 물질을 함유한다.
실시예 F7: 10mg의 활성 물질을 함유하는 앰플
조성
활성 물질 10.0mg
0.01 N 염산 충분량
이중 증류수를 2.0ml가 되도록 첨가한다.
조제
활성 물질을 0.01 N HCl의 필요량에 용해시키고, 염화나트륨과 등장으로 만들고, 무균 여과하고, 2ml 앰플에 옮겼다.
실시예 F8: 50mg의 활성 물질을 함유하는 앰플
조성
활성 물질 50.0mg
0.01 N 염산 충분량
이중 증류수를 10.0ml가 되도록 첨가한다.
조제
활성 물질을 0.01 N HCl의 필요량에 용해시키고, 염화나트륨과 등장으로 만 들고, 무균 여과하고, 10ml 앰플에 옮겼다.
실시예 F9: 5mg의 활성 물질을 함유하는 파우더 흡입용 캡슐
캡슐 1개의 함유량
활성 물질 5.0mg
흡입용 락토즈 15.0mg
20.0mg
조제
활성 물질을 흡입용 락토즈와 혼합하였다. 혼합물을 캡슐 제조 기계에서 캡슐에 담았다(빈 캡슐의 중량 약 50 mg).
캡슐의 중량: 70.0mg
캡슐 크기 = 크기 3
실시예 F10: 2.5mg 활성 물질을 함유하는 소형 분무기용 흡입용 용액
스프레이 1개의 함유량
활성 물질 2.500mg
벤즈알코늄 클로라이드 0.001mg
1N 염산 충분량
에탄올/물 (50/50)을 15.000mg가 되도록 첨가한다.
조제
활성 물질 및 벤즈알코늄 클로라이드를 에탄올/물 (50/50)에 용해시킨다. 용액의 pH를 1N 염산으로 조정한다. 생성 용액을 여과하고 소형 분무기(카트리지)에 사용되는 적합한 용기에 옮긴다.
용기의 함유량: 4.5 g
Claims (13)
- 화합물 3-Z-[1-(4-(N-((4-메틸-피페라진-1-일)-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논 또는 이의 토오토머, 디아스테레오머, 에난티오머, 이의 혼합물, 또는 이의 염을 포함하는, 특발성 폐 섬유증을 예방 또는 치료하기 위한 약제학적 조성물.
- 제1항에 있어서, 상기 화합물 3-Z-[1-(4-(N-((4-메틸-피페라진-1-일)-메틸카보닐)-N-메틸-아미노)-아닐리노)-1-페닐-메틸렌]-6-메톡시카보닐-2-인돌리논의 모노에탄설포네이트 염을 포함하는 약제학적 조성물.
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PCT/EP2005/057002 WO2006067165A2 (en) | 2004-12-24 | 2005-12-21 | Indolidone derivatives for the treatment or prevention of fibrotic diseases |
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