ES2324710T3 - Indolinonas sustituidas con heterociclos y su uso como inhibidores de receptores de tirosina quinasa. - Google Patents

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Publication number

ES2324710T3

ES2324710T3 ES03757806T ES03757806T ES2324710T3 ES 2324710 T3 ES2324710 T3 ES 2324710T3 ES 03757806 T ES03757806 T ES 03757806T ES 03757806 T ES03757806 T ES 03757806T ES 2324710 T3 ES2324710 T3 ES 2324710T3

Authority

ES

Spain

Prior art keywords

group

alkyl

amino

quad

methylene

Prior art date

2002-09-12

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired - Lifetime

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• 239000003112 inhibitor Substances 0.000 title description 7
• 108091000080 Phosphotransferase Proteins 0.000 title description 2
• 102000020233 phosphotransferase Human genes 0.000 title description 2
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 443
• -1 quinoxalin-6-yl Chemical group 0.000 claims abstract description 284
• 150000001875 compounds Chemical class 0.000 claims abstract description 151
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 93
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 62
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 47
• 239000000203 mixture Substances 0.000 claims abstract description 35
• 150000003839 salts Chemical class 0.000 claims abstract description 26
• 229910052801 chlorine Inorganic materials 0.000 claims abstract description 23
• 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 22
• 229910052731 fluorine Inorganic materials 0.000 claims abstract description 20
• 239000011737 fluorine Substances 0.000 claims abstract description 20
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 17
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 17
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims abstract description 16
• 229910052794 bromium Inorganic materials 0.000 claims abstract description 15
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 15
• 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims abstract description 12
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract description 10
• 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 10
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 9
• 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 7
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims abstract description 7
• FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical group C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims abstract description 6
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims abstract description 6
• 125000004539 5-benzimidazolyl group Chemical group N1=CNC2=C1C=CC(=C2)* 0.000 claims abstract description 6
• 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 6
• 125000001607 1,2,3-triazol-1-yl group Chemical group [*]N1N=NC([H])=C1[H] 0.000 claims abstract description 4
• 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims abstract description 4
• 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims abstract description 4
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 4
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 4
• 125000003545 alkoxy group Chemical group 0.000 claims description 127
• 125000006842 cycloalkyleneimino group Chemical group 0.000 claims description 69
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 60
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 50
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 47
• 125000004429 atom Chemical group 0.000 claims description 41
• 125000003884 phenylalkyl group Chemical group 0.000 claims description 38
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 37
• 229910052739 hydrogen Inorganic materials 0.000 claims description 35
• 239000001257 hydrogen Substances 0.000 claims description 35
• 229910052757 nitrogen Inorganic materials 0.000 claims description 35
• 229910052717 sulfur Inorganic materials 0.000 claims description 32
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 31
• 238000006243 chemical reaction Methods 0.000 claims description 31
• 238000002360 preparation method Methods 0.000 claims description 29
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 29
• 125000003277 amino group Chemical group 0.000 claims description 28
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
• 125000004181 carboxyalkyl group Chemical group 0.000 claims description 27
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 27
• SXWOVUCGBCAXQL-DQSJHHFOSA-N methyl (3z)-3-[2,3-dihydro-1,4-benzodioxin-6-yl-[4-[[2-(dimethylamino)acetyl]-methylamino]anilino]methylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=C2OCCOC2=CC=1)\NC1=CC=C(N(C)C(=O)CN(C)C)C=C1 SXWOVUCGBCAXQL-DQSJHHFOSA-N 0.000 claims description 27
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 27
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 26
• 125000004434 sulfur atom Chemical group 0.000 claims description 26
• 229910052760 oxygen Inorganic materials 0.000 claims description 24
• 239000001301 oxygen Substances 0.000 claims description 24
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 19
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 17
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 17
• 239000000460 chlorine Substances 0.000 claims description 17
• 125000006239 protecting group Chemical group 0.000 claims description 17
• 229910052740 iodine Inorganic materials 0.000 claims description 16
• 125000003282 alkyl amino group Chemical group 0.000 claims description 15
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 15
• 239000007790 solid phase Substances 0.000 claims description 15
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 14
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 14
• 125000001072 heteroaryl group Chemical group 0.000 claims description 14
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 13
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
• 125000006325 2-propenyl amino group Chemical group [H]C([H])=C([H])C([H])([H])N([H])* 0.000 claims description 12
• 150000001412 amines Chemical class 0.000 claims description 12
• 238000000034 method Methods 0.000 claims description 12
• NALBLJLOBICXRH-UHFFFAOYSA-N dinitrogen monohydride Chemical compound N=[N] NALBLJLOBICXRH-UHFFFAOYSA-N 0.000 claims description 11
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 9
• 150000003951 lactams Chemical group 0.000 claims description 9
• 125000002993 cycloalkylene group Chemical group 0.000 claims description 8
• 239000003814 drug Substances 0.000 claims description 8
• 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
• 230000004663 cell proliferation Effects 0.000 claims description 7
• 239000000126 substance Substances 0.000 claims description 7
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 6
• 230000007062 hydrolysis Effects 0.000 claims description 6
• 238000006460 hydrolysis reaction Methods 0.000 claims description 6
• 230000003647 oxidation Effects 0.000 claims description 6
• 238000007254 oxidation reaction Methods 0.000 claims description 6
• 125000006850 spacer group Chemical group 0.000 claims description 6
• YAJULHYYDWJESD-IZHYLOQSSA-N (3z)-6-chloro-3-[[4-[(dimethylamino)methyl]anilino]-(1-methylbenzimidazol-5-yl)methylidene]-1h-indol-2-one Chemical compound C1=CC(CN(C)C)=CC=C1N\C(C=1C=C2N=CN(C)C2=CC=1)=C/1C2=CC=C(Cl)C=C2NC\1=O YAJULHYYDWJESD-IZHYLOQSSA-N 0.000 claims description 5
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 5
• 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims description 5
• 230000010933 acylation Effects 0.000 claims description 5
• 238000005917 acylation reaction Methods 0.000 claims description 5
• 125000003342 alkenyl group Chemical group 0.000 claims description 5
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
• 230000009435 amidation Effects 0.000 claims description 5
• 238000007112 amidation reaction Methods 0.000 claims description 5
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 5
• 230000032050 esterification Effects 0.000 claims description 5
• 238000005886 esterification reaction Methods 0.000 claims description 5
• 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 5
• 125000002950 monocyclic group Chemical group 0.000 claims description 5
• 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 5
• 238000006722 reduction reaction Methods 0.000 claims description 5
• 229920002554 vinyl polymer Polymers 0.000 claims description 5
• NWXVVFGMDWXASW-VHXPQNKSSA-N (3z)-3-[1,3-benzodioxol-5-yl-[4-[(dimethylamino)methyl]anilino]methylidene]-6-chloro-1h-indol-2-one Chemical compound C1=CC(CN(C)C)=CC=C1N\C(C=1C=C2OCOC2=CC=1)=C/1C2=CC=C(Cl)C=C2NC\1=O NWXVVFGMDWXASW-VHXPQNKSSA-N 0.000 claims description 4
• KWFUYECTBFRIRG-IZHYLOQSSA-N (3z)-3-[1,3-benzodioxol-5-yl-[4-[[ethyl(methyl)amino]methyl]anilino]methylidene]-6-chloro-1h-indol-2-one Chemical compound C1=CC(CN(C)CC)=CC=C1N\C(C=1C=C2OCOC2=CC=1)=C/1C2=CC=C(Cl)C=C2NC\1=O KWFUYECTBFRIRG-IZHYLOQSSA-N 0.000 claims description 4
• KSJXPOZSSRPFPB-IZHYLOQSSA-N (3z)-3-[2,3-dihydro-1,4-benzodioxin-6-yl-[4-(ethylaminomethyl)anilino]methylidene]-6-fluoro-1h-indol-2-one Chemical compound C1=CC(CNCC)=CC=C1N\C(C=1C=C2OCCOC2=CC=1)=C/1C2=CC=C(F)C=C2NC\1=O KSJXPOZSSRPFPB-IZHYLOQSSA-N 0.000 claims description 4
• ODEQWQXGCAYNQS-IZHYLOQSSA-N (3z)-6-chloro-3-[2,3-dihydro-1,4-benzodioxin-6-yl-[4-[(dimethylamino)methyl]anilino]methylidene]-1h-indol-2-one Chemical compound C1=CC(CN(C)C)=CC=C1N\C(C=1C=C2OCCOC2=CC=1)=C/1C2=CC=C(Cl)C=C2NC\1=O ODEQWQXGCAYNQS-IZHYLOQSSA-N 0.000 claims description 4
• LKURCHRXPCDQMT-IZHYLOQSSA-N (3z)-6-fluoro-3-[(1-methylbenzimidazol-5-yl)-[4-(1,2,4-triazol-1-ylmethyl)anilino]methylidene]-1h-indol-2-one Chemical compound C=1C=C2N(C)C=NC2=CC=1C(=C\1C2=CC=C(F)C=C2NC/1=O)\NC(C=C1)=CC=C1CN1C=NC=N1 LKURCHRXPCDQMT-IZHYLOQSSA-N 0.000 claims description 4
• 125000006563 (C1-3) alkylaminocarbonyl group Chemical group 0.000 claims description 4
• VEQYZZUJZDPFKE-VHXPQNKSSA-N 4-[[(z)-(6-fluoro-2-oxo-1h-indol-3-ylidene)-(1-methylbenzimidazol-5-yl)methyl]amino]-n,n-dimethylbenzamide Chemical compound C1=CC(C(=O)N(C)C)=CC=C1N\C(C=1C=C2N=CN(C)C2=CC=1)=C/1C2=CC=C(F)C=C2NC\1=O VEQYZZUJZDPFKE-VHXPQNKSSA-N 0.000 claims description 4
• 125000005157 alkyl carboxy group Chemical group 0.000 claims description 4
• 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 4
• 125000005129 aryl carbonyl group Chemical group 0.000 claims description 4
• 239000004202 carbamide Substances 0.000 claims description 4
• 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 4
• XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims description 4
• 239000003085 diluting agent Substances 0.000 claims description 4
• 125000005843 halogen group Chemical group 0.000 claims description 4
• 239000000463 material Substances 0.000 claims description 4
• ISQFIECKXMSFOU-ZIADKAODSA-N methyl (3z)-3-[2,3-dihydro-1,4-benzodioxin-6-yl-[4-[(4-methylpiperazin-1-yl)methyl]anilino]methylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=C2OCCOC2=CC=1)\NC(C=C1)=CC=C1CN1CCN(C)CC1 ISQFIECKXMSFOU-ZIADKAODSA-N 0.000 claims description 4
• YIFIFSOAJPIGIJ-DQSJHHFOSA-N n-[4-[[(z)-(6-chloro-2-oxo-1h-indol-3-ylidene)-(2,3-dihydro-1,4-benzodioxin-6-yl)methyl]amino]phenyl]-n-[2-(dimethylamino)ethyl]acetamide Chemical compound C1=CC(N(C(C)=O)CCN(C)C)=CC=C1N\C(C=1C=C2OCCOC2=CC=1)=C/1C2=CC=C(Cl)C=C2NC\1=O YIFIFSOAJPIGIJ-DQSJHHFOSA-N 0.000 claims description 4
• LMCVWVYZMQAGJZ-ZIADKAODSA-N n-[4-[[(z)-(6-chloro-2-oxo-1h-indol-3-ylidene)-(2,3-dihydro-1,4-benzodioxin-6-yl)methyl]amino]phenyl]-n-[2-(dimethylamino)ethyl]propanamide Chemical compound C1=CC(N(CCN(C)C)C(=O)CC)=CC=C1N\C(C=1C=C2OCCOC2=CC=1)=C/1C2=CC=C(Cl)C=C2NC\1=O LMCVWVYZMQAGJZ-ZIADKAODSA-N 0.000 claims description 4
• DVEVDZVUEOLBQR-ZIADKAODSA-N n-[4-[[(z)-(6-chloro-2-oxo-1h-indol-3-ylidene)-(2,3-dihydro-1,4-benzodioxin-6-yl)methyl]amino]phenyl]-n-[3-(dimethylamino)propyl]acetamide Chemical compound C1=CC(N(C(C)=O)CCCN(C)C)=CC=C1N\C(C=1C=C2OCCOC2=CC=1)=C/1C2=CC=C(Cl)C=C2NC\1=O DVEVDZVUEOLBQR-ZIADKAODSA-N 0.000 claims description 4
• JDSVKRGOXWZTOV-FLWNBWAVSA-N n-[4-[[(z)-(6-chloro-2-oxo-1h-indol-3-ylidene)-(2,3-dihydro-1,4-benzodioxin-6-yl)methyl]amino]phenyl]-n-[3-(dimethylamino)propyl]propanamide Chemical compound C1=CC(N(CCCN(C)C)C(=O)CC)=CC=C1N\C(C=1C=C2OCCOC2=CC=1)=C/1C2=CC=C(Cl)C=C2NC\1=O JDSVKRGOXWZTOV-FLWNBWAVSA-N 0.000 claims description 4
• WWULUXRSBUVGLP-FLWNBWAVSA-N n-[4-[[(z)-(6-chloro-2-oxo-1h-indol-3-ylidene)-quinoxalin-6-ylmethyl]amino]phenyl]-n-methyl-2-(4-methylpiperazin-1-yl)acetamide Chemical compound C=1C=C(N\C(=C/2C3=CC=C(Cl)C=C3NC\2=O)C=2C=C3N=CC=NC3=CC=2)C=CC=1N(C)C(=O)CN1CCN(C)CC1 WWULUXRSBUVGLP-FLWNBWAVSA-N 0.000 claims description 4
• NGHNVCYNFAUQID-ZIADKAODSA-N n-[4-[[(z)-1,3-benzodioxol-5-yl-(6-chloro-2-oxo-1h-indol-3-ylidene)methyl]amino]phenyl]-n-methyl-2-(4-methylpiperazin-1-yl)acetamide Chemical compound C=1C=C(N\C(=C/2C3=CC=C(Cl)C=C3NC\2=O)C=2C=C3OCOC3=CC=2)C=CC=1N(C)C(=O)CN1CCN(C)CC1 NGHNVCYNFAUQID-ZIADKAODSA-N 0.000 claims description 4
• NVIHLCZLWCZJBD-DQSJHHFOSA-N n-[4-[[(z)-2,3-dihydro-1,4-benzodioxin-6-yl-(6-fluoro-2-oxo-1h-indol-3-ylidene)methyl]amino]phenyl]-3-(dimethylamino)-n-methylpropanamide Chemical compound C1=CC(N(C)C(=O)CCN(C)C)=CC=C1N\C(C=1C=C2OCCOC2=CC=1)=C/1C2=CC=C(F)C=C2NC\1=O NVIHLCZLWCZJBD-DQSJHHFOSA-N 0.000 claims description 4
• HRPALFYCQQDKHS-FLWNBWAVSA-N n-[4-[[(z)-2,3-dihydro-1,4-benzodioxin-6-yl-(6-fluoro-2-oxo-1h-indol-3-ylidene)methyl]amino]phenyl]-n-[3-(dimethylamino)propyl]propanamide Chemical compound C1=CC(N(CCCN(C)C)C(=O)CC)=CC=C1N\C(C=1C=C2OCCOC2=CC=1)=C/1C2=CC=C(F)C=C2NC\1=O HRPALFYCQQDKHS-FLWNBWAVSA-N 0.000 claims description 4
• 125000005400 pyridylcarbonyl group Chemical group N1=C(C=CC=C1)C(=O)* 0.000 claims description 4
• 238000005932 reductive alkylation reaction Methods 0.000 claims description 4
• JTTYBEQWOFZMFP-RQZHXJHFSA-N (3z)-3-[1,3-benzodioxol-5-yl-[4-[(4-methylpiperazin-1-yl)methyl]anilino]methylidene]-6-chloro-1h-indol-2-one Chemical compound C1CN(C)CCN1CC(C=C1)=CC=C1N\C(C=1C=C2OCOC2=CC=1)=C/1C2=CC=C(Cl)C=C2NC\1=O JTTYBEQWOFZMFP-RQZHXJHFSA-N 0.000 claims description 3
• 239000003153 chemical reaction reagent Substances 0.000 claims description 3
• 229940079593 drug Drugs 0.000 claims description 3
• 125000006316 iso-butyl amino group Chemical group [H]N(*)C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
• 239000012948 isocyanate Substances 0.000 claims description 3
• 150000002513 isocyanates Chemical class 0.000 claims description 3
• IXJISIDVDXYLTI-RQZHXJHFSA-N methyl (3z)-3-[1,3-benzodioxol-5-yl-[4-(diethylaminomethyl)anilino]methylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(CN(CC)CC)=CC=C1N\C(C=1C=C2OCOC2=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O IXJISIDVDXYLTI-RQZHXJHFSA-N 0.000 claims description 3
• YDJNGVGZHOABKD-IZHYLOQSSA-N methyl (3z)-3-[1,3-benzodioxol-5-yl-[4-[(dimethylamino)methyl]anilino]methylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=C2OCOC2=CC=1)\NC1=CC=C(CN(C)C)C=C1 YDJNGVGZHOABKD-IZHYLOQSSA-N 0.000 claims description 3
• XUKMQAUQPSBMPQ-RQZHXJHFSA-N methyl (3z)-3-[1,3-benzodioxol-5-yl-[4-[2-(dimethylamino)ethyl-methylcarbamoyl]anilino]methylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=C2OCOC2=CC=1)\NC1=CC=C(C(=O)N(C)CCN(C)C)C=C1 XUKMQAUQPSBMPQ-RQZHXJHFSA-N 0.000 claims description 3
• VZCBAERILCJERL-QPLCGJKRSA-N methyl (3z)-3-[2,3-dihydro-1,4-benzodioxin-6-yl-[4-(ethylaminomethyl)anilino]methylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(CNCC)=CC=C1N\C(C=1C=C2OCCOC2=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O VZCBAERILCJERL-QPLCGJKRSA-N 0.000 claims description 3
• DJNBIJXUUAGOGV-DQSJHHFOSA-N methyl (3z)-3-[2,3-dihydro-1,4-benzodioxin-6-yl-[4-(pyrrolidin-1-ylmethyl)anilino]methylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=C2OCCOC2=CC=1)\NC(C=C1)=CC=C1CN1CCCC1 DJNBIJXUUAGOGV-DQSJHHFOSA-N 0.000 claims description 3
• HPODJPLRFPIIGJ-QPLCGJKRSA-N methyl (3z)-3-[2,3-dihydro-1,4-benzodioxin-6-yl-[4-[(dimethylamino)methyl]anilino]methylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=C2OCCOC2=CC=1)\NC1=CC=C(CN(C)C)C=C1 HPODJPLRFPIIGJ-QPLCGJKRSA-N 0.000 claims description 3
• MXWVZQNZTKXKKO-DQSJHHFOSA-N methyl (3z)-3-[2,3-dihydro-1,4-benzodioxin-6-yl-[4-[2-(dimethylamino)ethyl-methylcarbamoyl]anilino]methylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=C2OCCOC2=CC=1)\NC1=CC=C(C(=O)N(C)CCN(C)C)C=C1 MXWVZQNZTKXKKO-DQSJHHFOSA-N 0.000 claims description 3
• AOPHCTKRYHULCH-ZIADKAODSA-N methyl (3z)-3-[2,3-dihydro-1,4-benzodioxin-6-yl-[4-[3-(dimethylamino)propyl-methylcarbamoyl]anilino]methylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=C2OCCOC2=CC=1)\NC1=CC=C(C(=O)N(C)CCCN(C)C)C=C1 AOPHCTKRYHULCH-ZIADKAODSA-N 0.000 claims description 3
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