NO322746B1 - Indoliner, substituert i 6-stilling, og farmasoytisk preparat, samt anvendelse og fremstilling derav. - Google Patents

Indoliner, substituert i 6-stilling, og farmasoytisk preparat, samt anvendelse og fremstilling derav. Download PDF

Info

Publication number: NO322746B1
Authority: NO; Norway
Prior art keywords: group; alkyl; phenyl; amino; methylene
Prior art date: 1999-10-13

Application number

NO20021719A

Other languages

English (en)

Norwegian (no)

Other versions

NO20021719D0 (no

NO20021719L (no

Inventor

Armin Heckel

Rainer Walter

Gerald Juergen Roth

Walter Spevak

Ulrike Tontsch-Grunt

Jacobus Van Meel

Norbert Redemann

Frank Hilberg

Original Assignee

Boehringer Ingelheim Pharma

Priority date (The priority date 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 date listed.)

1999-10-13

Filing date

2002-04-11

Publication date

2006-12-04

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=26006858&utm_source=***_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=NO322746(B1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1999-10-13 Priority claimed from DE19949208A external-priority patent/DE19949208A1/de

2000-08-31 Priority claimed from DE2000142696 external-priority patent/DE10042696A1/de

2002-04-11 Application filed by Boehringer Ingelheim Pharma filed Critical Boehringer Ingelheim Pharma

2002-04-11 Publication of NO20021719D0 publication Critical patent/NO20021719D0/no

2002-04-11 Publication of NO20021719L publication Critical patent/NO20021719L/no

2006-12-04 Publication of NO322746B1 publication Critical patent/NO322746B1/no

Links

238000002360 preparation method Methods 0.000 title description 11
150000002476 indolines Chemical class 0.000 title description 3
239000008194 pharmaceutical composition Substances 0.000 title 1
-1 C 1-3 -Alkoxy Chemical group 0.000 claims description 197
150000001875 compounds Chemical class 0.000 claims description 142
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 124
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 120
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 114
125000000217 alkyl group Chemical group 0.000 claims description 97
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 90
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 69
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 64
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 62
229910052757 nitrogen Inorganic materials 0.000 claims description 51
125000004433 nitrogen atom Chemical group N* 0.000 claims description 50
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 46
125000003545 alkoxy group Chemical group 0.000 claims description 38
229910052801 chlorine Inorganic materials 0.000 claims description 38
229910052717 sulfur Inorganic materials 0.000 claims description 36
125000004434 sulfur atom Chemical group 0.000 claims description 36
125000006563 (C1-3) alkylaminocarbonyl group Chemical group 0.000 claims description 35
150000003839 salts Chemical class 0.000 claims description 34
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 33
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 32
239000000460 chlorine Substances 0.000 claims description 32
229910052760 oxygen Inorganic materials 0.000 claims description 32
239000001301 oxygen Substances 0.000 claims description 32
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 30
125000001072 heteroaryl group Chemical group 0.000 claims description 30
238000006243 chemical reaction Methods 0.000 claims description 29
229910052731 fluorine Inorganic materials 0.000 claims description 29
239000011737 fluorine Substances 0.000 claims description 29
125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims description 28
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 27
125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 26
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 25
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 25
125000006576 di-(C1-C3-alkyl)-aminocarbonyl group Chemical group 0.000 claims description 24
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 24
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 22
125000003282 alkyl amino group Chemical group 0.000 claims description 22
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 21
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 21
125000006239 protecting group Chemical group 0.000 claims description 21
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 20
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 20
125000000753 cycloalkyl group Chemical group 0.000 claims description 20
229910052740 iodine Inorganic materials 0.000 claims description 20
125000006602 (C1-C3) alkylsulfonylamino group Chemical group 0.000 claims description 19
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 19
229910052794 bromium Inorganic materials 0.000 claims description 18
239000007790 solid phase Substances 0.000 claims description 17
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 16
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 16
125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims description 15
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 15
125000004744 butyloxycarbonyl group Chemical group 0.000 claims description 15
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
125000003277 amino group Chemical group 0.000 claims description 14
229910052799 carbon Inorganic materials 0.000 claims description 14
125000004093 cyano group Chemical group *C#N 0.000 claims description 14
125000002993 cycloalkylene group Chemical group 0.000 claims description 14
150000003951 lactams Chemical group 0.000 claims description 14
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 14
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 13
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 13
125000006842 cycloalkyleneimino group Chemical group 0.000 claims description 13
NALBLJLOBICXRH-UHFFFAOYSA-N dinitrogen monohydride Chemical group N=[N] NALBLJLOBICXRH-UHFFFAOYSA-N 0.000 claims description 13
238000004519 manufacturing process Methods 0.000 claims description 13
125000001153 fluoro group Chemical group F* 0.000 claims description 12
239000001257 hydrogen Substances 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 12
125000001424 substituent group Chemical group 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 claims description 11
125000002950 monocyclic group Chemical group 0.000 claims description 11
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
238000000034 method Methods 0.000 claims description 10
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 9
125000001841 imino group Chemical group [H]N=* 0.000 claims description 9
125000006594 (C1-C3) alkylsulfony group Chemical group 0.000 claims description 8
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 8
150000001412 amines Chemical class 0.000 claims description 8
150000002148 esters Chemical class 0.000 claims description 8
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 8
125000002883 imidazolyl group Chemical group 0.000 claims description 8
125000001624 naphthyl group Chemical group 0.000 claims description 8
125000004430 oxygen atom Chemical group O* 0.000 claims description 8
125000003226 pyrazolyl group Chemical group 0.000 claims description 8
125000000168 pyrrolyl group Chemical group 0.000 claims description 8
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
125000006603 (C1-C3) alkylaminosulfonyl group Chemical group 0.000 claims description 7
125000005129 aryl carbonyl group Chemical group 0.000 claims description 7
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 7
125000001309 chloro group Chemical group Cl* 0.000 claims description 7
239000000825 pharmaceutical preparation Substances 0.000 claims description 7
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 6
125000002252 acyl group Chemical group 0.000 claims description 6
125000004103 aminoalkyl group Chemical group 0.000 claims description 6
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 6
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 6
125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 6
125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 claims description 6
125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 6
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 6
125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 6
230000003647 oxidation Effects 0.000 claims description 6
238000007254 oxidation reaction Methods 0.000 claims description 6
239000002243 precursor Substances 0.000 claims description 6
125000006850 spacer group Chemical group 0.000 claims description 6
125000003831 tetrazolyl group Chemical group 0.000 claims description 6
125000001425 triazolyl group Chemical group 0.000 claims description 6
125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 5
125000004769 (C1-C4) alkylsulfonyl 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
239000000969 carrier Substances 0.000 claims description 5
230000004663 cell proliferation Effects 0.000 claims description 5
239000003085 diluting agent Substances 0.000 claims description 5
230000032050 esterification Effects 0.000 claims description 5
238000005886 esterification reaction Methods 0.000 claims description 5
ORCLOYHXQJNMMX-IZHYLOQSSA-N ethyl (3z)-3-[[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=C1 ORCLOYHXQJNMMX-IZHYLOQSSA-N 0.000 claims description 5
GUSPUPJKTCNHOJ-VHXPQNKSSA-N methyl (3z)-3-[[4-(ethylaminomethyl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(CNCC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O GUSPUPJKTCNHOJ-VHXPQNKSSA-N 0.000 claims description 5
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 5
125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 4
230000010933 acylation Effects 0.000 claims description 4
238000005917 acylation reaction Methods 0.000 claims description 4
150000001408 amides Chemical class 0.000 claims description 4
125000002102 aryl alkyloxo group Chemical group 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
125000001246 bromo group Chemical group Br* 0.000 claims description 4
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
239000004202 carbamide Substances 0.000 claims description 4
150000001721 carbon Chemical group 0.000 claims description 4
XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims description 4
RTLQNDXPILJVLA-UHFFFAOYSA-N ethyl 2-hydroxy-3-[C-phenyl-N-[4-(piperidin-1-ylmethyl)phenyl]carbonimidoyl]-1H-indole-6-carboxylate Chemical compound CCOC(=O)C1=CC2=C(C=C1)C(=C(N2)O)C(=NC3=CC=C(C=C3)CN4CCCCC4)C5=CC=CC=C5 RTLQNDXPILJVLA-UHFFFAOYSA-N 0.000 claims description 4
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 4
125000000623 heterocyclic group Chemical group 0.000 claims description 4
125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
125000005935 hexyloxycarbonyl group Chemical group 0.000 claims description 4
230000007062 hydrolysis Effects 0.000 claims description 4
238000006460 hydrolysis reaction Methods 0.000 claims description 4
239000012948 isocyanate Substances 0.000 claims description 4
150000002513 isocyanates Chemical class 0.000 claims description 4
125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 claims description 4
CPMDPSXJELVGJG-UHFFFAOYSA-N methyl 2-hydroxy-3-[N-[4-[methyl-[2-(4-methylpiperazin-1-yl)acetyl]amino]phenyl]-C-phenylcarbonimidoyl]-1H-indole-6-carboxylate Chemical compound OC=1NC2=CC(=CC=C2C=1C(=NC1=CC=C(C=C1)N(C(CN1CCN(CC1)C)=O)C)C1=CC=CC=C1)C(=O)OC CPMDPSXJELVGJG-UHFFFAOYSA-N 0.000 claims description 4
125000001148 pentyloxycarbonyl group Chemical group 0.000 claims description 4
125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 4
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 4
125000005544 phthalimido group Chemical group 0.000 claims description 4
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 4
125000004742 propyloxycarbonyl group Chemical group 0.000 claims description 4
125000004076 pyridyl group Chemical group 0.000 claims description 4
125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
230000009467 reduction Effects 0.000 claims description 4
238000006722 reduction reaction Methods 0.000 claims description 4
238000005932 reductive alkylation reaction Methods 0.000 claims description 4
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 3
125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 3
125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
IXKSURGKVWEOIW-DQSJHHFOSA-N ethyl (3z)-3-[[4-[acetyl-[2-(dimethylamino)ethyl]amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(CCN(C)C)C(C)=O)C=C1 IXKSURGKVWEOIW-DQSJHHFOSA-N 0.000 claims description 3
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 3
125000002541 furyl group Chemical group 0.000 claims description 3
150000004820 halides Chemical class 0.000 claims description 3
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 claims description 3
UTEHGZFZMLODQF-VHXPQNKSSA-N methyl (3z)-3-[[4-(1-methylimidazol-2-yl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1C1=NC=CN1C UTEHGZFZMLODQF-VHXPQNKSSA-N 0.000 claims description 3
PKXSPUDURLLHHG-RQZHXJHFSA-N methyl (3z)-3-[[4-[acetyl-[2-(dimethylamino)-2-oxoethyl]amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(CC(=O)N(C)C)C(C)=O)C=C1 PKXSPUDURLLHHG-RQZHXJHFSA-N 0.000 claims description 3
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 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 3
150000007522 mineralic acids Chemical class 0.000 claims description 3
150000002825 nitriles Chemical class 0.000 claims description 3
150000007524 organic acids Chemical class 0.000 claims description 3
238000006277 sulfonation reaction Methods 0.000 claims description 3
125000006597 (C1-C3) alkylcarbonylamino group Chemical group 0.000 claims description 2
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 2
125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 2
125000006164 6-membered heteroaryl group Chemical group 0.000 claims description 2
230000002159 abnormal effect Effects 0.000 claims description 2
125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 2
125000006310 cycloalkyl amino group Chemical group 0.000 claims description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
IVIFECJEIKPXDF-RQZHXJHFSA-N ethyl (3z)-3-[[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=C1 IVIFECJEIKPXDF-RQZHXJHFSA-N 0.000 claims description 2
NETCICHFVHZSSG-ZIADKAODSA-N ethyl (3z)-3-[[4-[acetyl-[3-(dimethylamino)propyl]amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(CCCN(C)C)C(C)=O)C=C1 NETCICHFVHZSSG-ZIADKAODSA-N 0.000 claims description 2
125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
ZQQCIGZFIKNSLX-RQZHXJHFSA-N methyl (3z)-3-[[4-[3-(dimethylamino)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)\NC1=CC=C(N(CCCN(C)C)S(C)(=O)=O)C=C1 ZQQCIGZFIKNSLX-RQZHXJHFSA-N 0.000 claims description 2
VBLVPTZXOOSQHZ-QPLCGJKRSA-N methyl (3z)-3-[[4-[[2-(dimethylamino)acetyl]-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CN(C)C)C=C1 VBLVPTZXOOSQHZ-QPLCGJKRSA-N 0.000 claims description 2
125000002971 oxazolyl group Chemical group 0.000 claims description 2
125000003373 pyrazinyl group Chemical group 0.000 claims description 2
125000002098 pyridazinyl group Chemical group 0.000 claims description 2
125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
239000000126 substance Substances 0.000 claims description 2
125000000335 thiazolyl group Chemical group 0.000 claims description 2
125000001544 thienyl group Chemical group 0.000 claims description 2
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 2
CREXVNNSNOKDHW-UHFFFAOYSA-N azaniumylideneazanide Chemical group N[N] CREXVNNSNOKDHW-UHFFFAOYSA-N 0.000 claims 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
240000007594 Oryza sativa Species 0.000 claims 1
235000007164 Oryza sativa Nutrition 0.000 claims 1
125000002346 iodo group Chemical group I* 0.000 claims 1
KUZBKIYSYFCFOT-QPLCGJKRSA-N methyl (3z)-3-[[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=C1 KUZBKIYSYFCFOT-QPLCGJKRSA-N 0.000 claims 1
235000009566 rice Nutrition 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 837
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 729
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 227
239000000741 silica gel Substances 0.000 description 227
229910002027 silica gel Inorganic materials 0.000 description 227
238000000119 electrospray ionisation mass spectrum Methods 0.000 description 185
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 182
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 90
238000001819 mass spectrum Methods 0.000 description 80
229920005989 resin Polymers 0.000 description 80
239000011347 resin Substances 0.000 description 80
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 65
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 62
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 59
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238000003756 stirring Methods 0.000 description 8
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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 7
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UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
239000011780 sodium chloride Substances 0.000 description 7
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RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
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ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 6
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 6
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239000003480 eluent Substances 0.000 description 6
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 6
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 6
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 6
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 6
ATBIAJXSKNPHEI-UHFFFAOYSA-N pyridine-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=CN=C1 ATBIAJXSKNPHEI-UHFFFAOYSA-N 0.000 description 6
NCDBSOTWFCLPFG-FCQUAONHSA-N (3z)-3-[[4-[(dimethylamino)methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylic acid Chemical compound C1=CC(CN(C)C)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(O)=O)C=C2NC\1=O NCDBSOTWFCLPFG-FCQUAONHSA-N 0.000 description 5
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GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 5
WOJBIBHVUSZAGS-UHFFFAOYSA-N 3-[(dimethylamino)methyl]aniline Chemical compound CN(C)CC1=CC=CC(N)=C1 WOJBIBHVUSZAGS-UHFFFAOYSA-N 0.000 description 5
DRYFDUUAYSVNSN-UHFFFAOYSA-N 4-(piperidin-1-ylmethyl)aniline Chemical compound C1=CC(N)=CC=C1CN1CCCCC1 DRYFDUUAYSVNSN-UHFFFAOYSA-N 0.000 description 5
RIQLJIOFWJEUCA-UHFFFAOYSA-N 4-[[benzyl(methyl)amino]methyl]aniline Chemical compound C=1C=C(N)C=CC=1CN(C)CC1=CC=CC=C1 RIQLJIOFWJEUCA-UHFFFAOYSA-N 0.000 description 5
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 5
239000002775 capsule Substances 0.000 description 5
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 5
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 5
UZPJPADJORIKJY-MVJHLKBCSA-N ethyl (3z)-3-[[4-[[benzyl(ethyl)amino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CN(CC)CC1=CC=CC=C1 UZPJPADJORIKJY-MVJHLKBCSA-N 0.000 description 5
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 5
239000000706 filtrate Substances 0.000 description 5
230000002401 inhibitory effect Effects 0.000 description 5
TXCOFUNEYLUKHR-UHFFFAOYSA-N n-(4-aminophenyl)-n-[2-(dimethylamino)ethyl]methanesulfonamide Chemical compound CN(C)CCN(S(C)(=O)=O)C1=CC=C(N)C=C1 TXCOFUNEYLUKHR-UHFFFAOYSA-N 0.000 description 5
FPWNRFBIGPQPMH-UHFFFAOYSA-N n-methyl-n-(4-nitrophenyl)prop-2-enamide Chemical compound C=CC(=O)N(C)C1=CC=C([N+]([O-])=O)C=C1 FPWNRFBIGPQPMH-UHFFFAOYSA-N 0.000 description 5
239000007800 oxidant agent Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
SFEAIUCOZWDYMJ-UHFFFAOYSA-N 4-(pyrrolidin-1-ylmethyl)aniline Chemical compound C1=CC(N)=CC=C1CN1CCCC1 SFEAIUCOZWDYMJ-UHFFFAOYSA-N 0.000 description 4
OXTPGYNBWHJWOR-UHFFFAOYSA-N 4-[(2,6-dimethylpiperidin-1-yl)methyl]aniline Chemical compound CC1CCCC(C)N1CC1=CC=C(N)C=C1 OXTPGYNBWHJWOR-UHFFFAOYSA-N 0.000 description 4
NNCCQALFJIMRKB-UHFFFAOYSA-N 4-[(dimethylamino)methyl]aniline Chemical compound CN(C)CC1=CC=C(N)C=C1 NNCCQALFJIMRKB-UHFFFAOYSA-N 0.000 description 4
IMMDNRXGZICMBC-UHFFFAOYSA-N 4-[2-(diethylamino)ethyl]aniline Chemical compound CCN(CC)CCC1=CC=C(N)C=C1 IMMDNRXGZICMBC-UHFFFAOYSA-N 0.000 description 4
108091007914 CDKs Proteins 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
102000016736 Cyclin Human genes 0.000 description 4
108050006400 Cyclin Proteins 0.000 description 4
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
239000012317 TBTU Substances 0.000 description 4
CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 4
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
238000001816 cooling Methods 0.000 description 4
201000010099 disease Diseases 0.000 description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
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 4
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 4
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 4
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 4
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 4
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 4
MUAUVCXWMHWZHJ-FLWNBWAVSA-N ethyl (3z)-3-[[4-[(2,6-dimethylpiperidin-1-yl)methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CN1C(C)CCCC1C MUAUVCXWMHWZHJ-FLWNBWAVSA-N 0.000 description 4
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 4
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 4
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 4
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 4
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 4
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 4
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 4
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 4
NPMGCBPWXXVSJG-DQSJHHFOSA-N ethyl (3z)-3-[[4-[methyl(piperidine-1-carbonyl)amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1N(C)C(=O)N1CCCCC1 NPMGCBPWXXVSJG-DQSJHHFOSA-N 0.000 description 4
IDUOPIZEQCZLER-ZIADKAODSA-N ethyl (3z)-3-[[4-[methyl-(2-morpholin-4-ylacetyl)amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1N(C)C(=O)CN1CCOCC1 IDUOPIZEQCZLER-ZIADKAODSA-N 0.000 description 4
238000011049 filling Methods 0.000 description 4
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 4
239000005457 ice water Substances 0.000 description 4
239000003112 inhibitor Substances 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
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 4
RWGCGSGXCAVHHS-UHFFFAOYSA-N methyl 3-[N-[4-[(dimethylamino)methyl]phenyl]-C-phenylcarbonimidoyl]-2-hydroxy-1H-indole-6-carboxylate Chemical compound CN(C)CC1=CC=C(C=C1)N=C(C2=CC=CC=C2)C3=C(NC4=C3C=CC(=C4)C(=O)OC)O RWGCGSGXCAVHHS-UHFFFAOYSA-N 0.000 description 4
NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 4
DDMUYJXZBNUDNC-UHFFFAOYSA-N n-(4-aminophenyl)-n-[2-(dimethylamino)ethyl]propanamide Chemical compound CN(C)CCN(C(=O)CC)C1=CC=C(N)C=C1 DDMUYJXZBNUDNC-UHFFFAOYSA-N 0.000 description 4
QKKGJBCRUWXLRD-UHFFFAOYSA-N n-methyl-1-(4-methylphenyl)-n-[(4-nitrophenyl)methyl]methanamine Chemical compound C=1C=C([N+]([O-])=O)C=CC=1CN(C)CC1=CC=C(C)C=C1 QKKGJBCRUWXLRD-UHFFFAOYSA-N 0.000 description 4
FWYRKLVNWYDPLY-UHFFFAOYSA-N n-methyl-n-[(4-nitrophenyl)methyl]propan-1-amine Chemical compound CCCN(C)CC1=CC=C([N+]([O-])=O)C=C1 FWYRKLVNWYDPLY-UHFFFAOYSA-N 0.000 description 4
229910052700 potassium Inorganic materials 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
238000010992 reflux Methods 0.000 description 4
238000000926 separation method Methods 0.000 description 4
JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 4
239000000829 suppository Substances 0.000 description 4
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RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
239000008215 water for injection Substances 0.000 description 4
HDPNBNXLBDFELL-UHFFFAOYSA-N 1,1,1-trimethoxyethane Chemical compound COC(C)(OC)OC HDPNBNXLBDFELL-UHFFFAOYSA-N 0.000 description 3
GJKIAPNNPWBCOF-UHFFFAOYSA-N 2-(4-nitrophenyl)-1h-imidazole Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=NC=CN1 GJKIAPNNPWBCOF-UHFFFAOYSA-N 0.000 description 3
KBAVWAIJZRUOMZ-UHFFFAOYSA-N 2-(n-methylsulfonyl-4-nitroanilino)acetic acid Chemical compound OC(=O)CN(S(=O)(=O)C)C1=CC=C([N+]([O-])=O)C=C1 KBAVWAIJZRUOMZ-UHFFFAOYSA-N 0.000 description 3
SYZRZLUNWVNNNV-UHFFFAOYSA-N 2-bromoacetyl chloride Chemical compound ClC(=O)CBr SYZRZLUNWVNNNV-UHFFFAOYSA-N 0.000 description 3
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
ZHOYVFPSBCXAGM-UHFFFAOYSA-N 4-(5-methyl-1h-imidazol-4-yl)aniline Chemical compound N1C=NC(C=2C=CC(N)=CC=2)=C1C ZHOYVFPSBCXAGM-UHFFFAOYSA-N 0.000 description 3
DGHAOTHIDTUSJY-UHFFFAOYSA-N 4-(imidazol-1-ylmethyl)aniline Chemical compound C1=CC(N)=CC=C1CN1C=NC=C1 DGHAOTHIDTUSJY-UHFFFAOYSA-N 0.000 description 3
WNYFVEFUHMDIRQ-UHFFFAOYSA-N 4-(morpholin-4-ylmethyl)aniline Chemical compound C1=CC(N)=CC=C1CN1CCOCC1 WNYFVEFUHMDIRQ-UHFFFAOYSA-N 0.000 description 3
TZMCILRCGMFRJC-UHFFFAOYSA-N 4-[(1,1-dioxo-1,4-thiazinan-4-yl)methyl]aniline Chemical compound C1=CC(N)=CC=C1CN1CCS(=O)(=O)CC1 TZMCILRCGMFRJC-UHFFFAOYSA-N 0.000 description 3
MKTORDFOADPMDB-UHFFFAOYSA-N 4-[(1-oxo-1,4-thiazinan-4-yl)methyl]aniline Chemical compound C1=CC(N)=CC=C1CN1CCS(=O)CC1 MKTORDFOADPMDB-UHFFFAOYSA-N 0.000 description 3
NZEPOTOSLXJCLQ-UHFFFAOYSA-N 4-[(4-nitrophenyl)methyl]thiomorpholine Chemical compound C1=CC([N+](=O)[O-])=CC=C1CN1CCSCC1 NZEPOTOSLXJCLQ-UHFFFAOYSA-N 0.000 description 3
QXFFKXNNVCXHSJ-UHFFFAOYSA-N 4-[[bis(2-methylpropyl)amino]methyl]aniline Chemical compound CC(C)CN(CC(C)C)CC1=CC=C(N)C=C1 QXFFKXNNVCXHSJ-UHFFFAOYSA-N 0.000 description 3
UZARQBVTRHEUOB-UHFFFAOYSA-N 4-n-cyclohexylbenzene-1,4-diamine Chemical compound C1=CC(N)=CC=C1NC1CCCCC1 UZARQBVTRHEUOB-UHFFFAOYSA-N 0.000 description 3
VTSUWHFLMJLYKN-UHFFFAOYSA-N 4-nitro-n-propan-2-ylaniline Chemical compound CC(C)NC1=CC=C([N+]([O-])=O)C=C1 VTSUWHFLMJLYKN-UHFFFAOYSA-N 0.000 description 3
QZKDRJGIYLVIML-UHFFFAOYSA-N 7-methyl-3-[(4-nitrophenyl)methyl]-1,2,4,5-tetrahydro-3-benzazepine Chemical compound C1CC2=CC(C)=CC=C2CCN1CC1=CC=C([N+]([O-])=O)C=C1 QZKDRJGIYLVIML-UHFFFAOYSA-N 0.000 description 3
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 3
239000012448 Lithium borohydride Substances 0.000 description 3
PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
206010028980 Neoplasm Diseases 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
239000007868 Raney catalyst Substances 0.000 description 3
229910000564 Raney nickel Inorganic materials 0.000 description 3
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 3
HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 3
239000013543 active substance Substances 0.000 description 3
239000003513 alkali Substances 0.000 description 3
229960004050 aminobenzoic acid Drugs 0.000 description 3
230000033115 angiogenesis Effects 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
229960004106 citric acid Drugs 0.000 description 3
235000015165 citric acid Nutrition 0.000 description 3
230000000694 effects Effects 0.000 description 3
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 3
LNBFSXVABYNAAP-GYHWCHFESA-N ethyl (3z)-2-oxo-3-[1-[4-(piperidin-1-ylmethyl)anilino]propylidene]-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(/CC)NC(C=C1)=CC=C1CN1CCCCC1 LNBFSXVABYNAAP-GYHWCHFESA-N 0.000 description 3
PUDXYNKJCBNWGO-RQZHXJHFSA-N ethyl (3z)-2-oxo-3-[[4-[(1-oxo-1,4-thiazinan-4-yl)methyl]anilino]-phenylmethylidene]-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CN1CCS(=O)CC1 PUDXYNKJCBNWGO-RQZHXJHFSA-N 0.000 description 3
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 3
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 3
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 3
QOPFVEUTNDXQNA-RQZHXJHFSA-N ethyl (3z)-3-[[4-[[2-(ethylamino)acetyl]-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(C)C(=O)CNCC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OCC)C=C2NC\1=O QOPFVEUTNDXQNA-RQZHXJHFSA-N 0.000 description 3
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 3
HRZROZNKFNVLLX-IZHYLOQSSA-N ethyl (3z)-3-[[4-[acetyl(methyl)amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(C)=O)C=C1 HRZROZNKFNVLLX-IZHYLOQSSA-N 0.000 description 3
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 3
AVTNJZHIJVLNJD-FCQUAONHSA-N ethyl (3z)-3-[[4-[carbamoyl(methyl)amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(N)=O)C=C1 AVTNJZHIJVLNJD-FCQUAONHSA-N 0.000 description 3
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 3
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 3
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 3
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 3
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 3
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 3
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 3
MCHMCUJNESZUOB-UHFFFAOYSA-N ethyl 2-[[2-(4-benzylpiperazin-1-yl)-5-nitrobenzoyl]amino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate Chemical compound S1C=2CCCCC=2C(C(=O)OCC)=C1NC(=O)C1=CC([N+]([O-])=O)=CC=C1N(CC1)CCN1CC1=CC=CC=C1 MCHMCUJNESZUOB-UHFFFAOYSA-N 0.000 description 3
229960002897 heparin Drugs 0.000 description 3
229920000669 heparin Polymers 0.000 description 3
229940098779 methanesulfonic acid Drugs 0.000 description 3
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 3
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RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000003125 aqueous solvent Substances 0.000 description 2
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
230000004071 biological effect Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 2
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
238000001035 drying Methods 0.000 description 2
102000052116 epidermal growth factor receptor activity proteins Human genes 0.000 description 2
108700015053 epidermal growth factor receptor activity proteins Proteins 0.000 description 2
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 2
JRTGTGDTUBRIHW-RQZHXJHFSA-N ethyl (3z)-2-oxo-3-[phenyl-(4-pyridin-2-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=CC=N1 JRTGTGDTUBRIHW-RQZHXJHFSA-N 0.000 description 2
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 2
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 2
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 2
ZYCDRARJJONYTR-QPLCGJKRSA-N ethyl (3z)-3-[[4-(imidazol-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=C1CN1C=CN=C1 ZYCDRARJJONYTR-QPLCGJKRSA-N 0.000 description 2
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 2
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 2
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 2
XREDDDJIQONGFW-ZIADKAODSA-N ethyl (3z)-3-[[4-[[2-(dimethylamino)-2-oxoethyl]-propanoylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(CC(=O)N(C)C)C(=O)CC)C=C1 XREDDDJIQONGFW-ZIADKAODSA-N 0.000 description 2
BLWGPVVOVJBMON-KTMFPKCZSA-N ethyl (3z)-3-[[4-[[benzyl(methyl)amino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CN(C)CC1=CC=CC=C1 BLWGPVVOVJBMON-KTMFPKCZSA-N 0.000 description 2
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 2
SQQLRRLMSFILOE-KTMFPKCZSA-N ethyl (3z)-3-[[4-[acetyl(2-piperidin-1-ylethyl)amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1N(C(C)=O)CCN1CCCCC1 SQQLRRLMSFILOE-KTMFPKCZSA-N 0.000 description 2
IJGHXPNCEXZUIU-JWGURIENSA-N ethyl (3z)-3-[[4-[acetyl-[3-(dimethylamino)propyl]amino]anilino]methylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C\NC1=CC=C(N(CCCN(C)C)C(C)=O)C=C1 IJGHXPNCEXZUIU-JWGURIENSA-N 0.000 description 2
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 2
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 2
RCYLCCWUDSYRNK-UHFFFAOYSA-N ethyl 1-acetyl-3-(1-ethoxypropylidene)-2-oxoindole-6-carboxylate Chemical compound CCOC(=O)C1=CC=C2C(=C(CC)OCC)C(=O)N(C(C)=O)C2=C1 RCYLCCWUDSYRNK-UHFFFAOYSA-N 0.000 description 2
PKDYOKKJAIBJNK-UHFFFAOYSA-N ethyl 2-[(4-aminophenyl)methyl-methylamino]acetate Chemical compound CCOC(=O)CN(C)CC1=CC=C(N)C=C1 PKDYOKKJAIBJNK-UHFFFAOYSA-N 0.000 description 2
SDMAVFXBWFYTCI-UHFFFAOYSA-N ethyl 2-oxo-1,3-dihydroindole-6-carboxylate Chemical compound CCOC(=O)C1=CC=C2CC(=O)NC2=C1 SDMAVFXBWFYTCI-UHFFFAOYSA-N 0.000 description 2
JLXBWVAKVCYKNB-UHFFFAOYSA-N ethyl 4-(2-methoxy-2-oxoethyl)-3-nitrobenzoate Chemical compound CCOC(=O)C1=CC=C(CC(=O)OC)C([N+]([O-])=O)=C1 JLXBWVAKVCYKNB-UHFFFAOYSA-N 0.000 description 2
LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 2
239000012091 fetal bovine serum Substances 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 2
239000008273 gelatin Substances 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
239000007903 gelatin capsule Substances 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
235000011852 gelatine desserts Nutrition 0.000 description 2
239000008187 granular material Substances 0.000 description 2
201000011066 hemangioma Diseases 0.000 description 2
210000005260 human cell Anatomy 0.000 description 2
JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000000594 mannitol Substances 0.000 description 2
235000010355 mannitol Nutrition 0.000 description 2
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 2
BDIXPOBFDVYSJA-IZHYLOQSSA-N methyl (3z)-3-[[4-(imidazol-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=C1CN1C=CN=C1 BDIXPOBFDVYSJA-IZHYLOQSSA-N 0.000 description 2
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 2
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 2
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 2
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 2
UTWGGRJAZSHAAZ-RQZHXJHFSA-N methyl (3z)-3-[[4-[[(2-ethoxy-2-oxoethyl)-methylamino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(CN(C)CC(=O)OCC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O UTWGGRJAZSHAAZ-RQZHXJHFSA-N 0.000 description 2
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 2
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 2
IWFYADKEUUNZOQ-QPLCGJKRSA-N methyl (3z)-3-[[4-[[3-aminopropyl(methyl)amino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(C)CCCN)C=C1 IWFYADKEUUNZOQ-QPLCGJKRSA-N 0.000 description 2
HHZUYGKJQCTQLM-VHXPQNKSSA-N methyl (3z)-3-[[4-[acetyl(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(C)=O)C=C1 HHZUYGKJQCTQLM-VHXPQNKSSA-N 0.000 description 2
NFDQVNGHDIJKMW-VHXPQNKSSA-N methyl (3z)-3-[[4-[cyanomethyl(methylsulfonyl)amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(CC#N)S(C)(=O)=O)C=C1 NFDQVNGHDIJKMW-VHXPQNKSSA-N 0.000 description 2
LZXXNPOYQCLXRS-UHFFFAOYSA-N methyl 4-aminobenzoate Chemical compound COC(=O)C1=CC=C(N)C=C1 LZXXNPOYQCLXRS-UHFFFAOYSA-N 0.000 description 2
JLKRJHPQNYVSGM-UHFFFAOYSA-N methyl-(4-nitro-benzyl)-amine Chemical compound CNCC1=CC=C([N+]([O-])=O)C=C1 JLKRJHPQNYVSGM-UHFFFAOYSA-N 0.000 description 2
238000002156 mixing Methods 0.000 description 2
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HVOYZOQVDYHUPF-UHFFFAOYSA-N n,n',n'-trimethylethane-1,2-diamine Chemical compound CNCCN(C)C HVOYZOQVDYHUPF-UHFFFAOYSA-N 0.000 description 2
SORARJZLMNRBAQ-UHFFFAOYSA-N n,n',n'-trimethylpropane-1,3-diamine Chemical compound CNCCCN(C)C SORARJZLMNRBAQ-UHFFFAOYSA-N 0.000 description 2
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NRCLQRUDKZTTER-UHFFFAOYSA-N n-(4-aminophenyl)-3-(dimethylamino)-n-methylpropanamide Chemical compound CN(C)CCC(=O)N(C)C1=CC=C(N)C=C1 NRCLQRUDKZTTER-UHFFFAOYSA-N 0.000 description 2
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USVINCOWSQFSNU-UHFFFAOYSA-N n-(4-aminophenyl)-n-[2-(dimethylamino)ethyl]pyridine-3-carboxamide Chemical compound C=1C=C(N)C=CC=1N(CCN(C)C)C(=O)C1=CC=CN=C1 USVINCOWSQFSNU-UHFFFAOYSA-N 0.000 description 2
WFWDHVMQQIVLNN-UHFFFAOYSA-N n-(4-aminophenyl)-n-[3-(dimethylamino)propyl]acetamide Chemical compound CN(C)CCCN(C(C)=O)C1=CC=C(N)C=C1 WFWDHVMQQIVLNN-UHFFFAOYSA-N 0.000 description 2
GCQFMJFKLZDMRV-UHFFFAOYSA-N n-(4-aminophenyl)-n-methyl-2-morpholin-4-ylacetamide Chemical compound C=1C=C(N)C=CC=1N(C)C(=O)CN1CCOCC1 GCQFMJFKLZDMRV-UHFFFAOYSA-N 0.000 description 2
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WZFCLDKJJMFMPI-UHFFFAOYSA-N n-(4-aminophenyl)-n-methyl-2-pyrrolidin-1-ylacetamide Chemical compound C=1C=C(N)C=CC=1N(C)C(=O)CN1CCCC1 WZFCLDKJJMFMPI-UHFFFAOYSA-N 0.000 description 2
MGDIHQKVMQJZOD-UHFFFAOYSA-N n-(4-aminophenyl)-n-methyl-3-piperidin-1-ylpropanamide Chemical compound C=1C=C(N)C=CC=1N(C)C(=O)CCN1CCCCC1 MGDIHQKVMQJZOD-UHFFFAOYSA-N 0.000 description 2
QFELUFGHFLYZEZ-UHFFFAOYSA-N n-(4-aminophenyl)-n-methylacetamide Chemical compound CC(=O)N(C)C1=CC=C(N)C=C1 QFELUFGHFLYZEZ-UHFFFAOYSA-N 0.000 description 2
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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
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
JRGQSUPXYLJIGB-JCMHNJIXSA-N ethyl (3z)-3-[1-[4-[[2-(dimethylamino)acetyl]-methylamino]anilino]ethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(/C)NC1=CC=C(N(C)C(=O)CN(C)C)C=C1 JRGQSUPXYLJIGB-JCMHNJIXSA-N 0.000 description 1
HRDUWDJLEWNFMR-ATJXCDBQSA-N ethyl (3z)-3-[1-[4-[[2-(dimethylamino)acetyl]-methylamino]anilino]propylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(/CC)NC1=CC=C(N(C)C(=O)CN(C)C)C=C1 HRDUWDJLEWNFMR-ATJXCDBQSA-N 0.000 description 1
FPCAYZUZSJHFLE-LCUIJRPUSA-N ethyl (3z)-3-[1-[4-[acetyl-[3-(dimethylamino)propyl]amino]anilino]butylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C/1NC2=CC(C(=O)OCC)=CC=C2C\1=C(/CCC)NC1=CC=C(N(CCCN(C)C)C(C)=O)C=C1 FPCAYZUZSJHFLE-LCUIJRPUSA-N 0.000 description 1
QERMALCKFDOHQZ-ULJHMMPZSA-N ethyl (3z)-3-[1-[4-[acetyl-[3-(dimethylamino)propyl]amino]anilino]ethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(/C)NC1=CC=C(N(CCCN(C)C)C(C)=O)C=C1 QERMALCKFDOHQZ-ULJHMMPZSA-N 0.000 description 1
HPRDNJKLSHVSFW-BZZOAKBMSA-N ethyl (3z)-3-[1-[4-[acetyl-[3-(dimethylamino)propyl]amino]anilino]propylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(/CC)NC1=CC=C(N(CCCN(C)C)C(C)=O)C=C1 HPRDNJKLSHVSFW-BZZOAKBMSA-N 0.000 description 1
YGASJVGLHJEVQF-IZHYLOQSSA-N ethyl (3z)-3-[[3,5-dibromo-4-[(dimethylamino)methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC(Br)=C(CN(C)C)C(Br)=C1 YGASJVGLHJEVQF-IZHYLOQSSA-N 0.000 description 1
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
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
GHWFWNCLIGQYCE-RQZHXJHFSA-N ethyl (3z)-3-[[3-amino-4-[[2-(dimethylamino)acetyl]-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CN(C)C)C(N)=C1 GHWFWNCLIGQYCE-RQZHXJHFSA-N 0.000 description 1
TZJRNTBXNYWUCH-IZHYLOQSSA-N ethyl (3z)-3-[[3-bromo-4-[(dimethylamino)methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(C)C)C(Br)=C1 TZJRNTBXNYWUCH-IZHYLOQSSA-N 0.000 description 1
MGHYPWDVRBOKQH-RQZHXJHFSA-N ethyl (3z)-3-[[3-bromo-4-[[2-(dimethylamino)acetyl]-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CN(C)C)C(Br)=C1 MGHYPWDVRBOKQH-RQZHXJHFSA-N 0.000 description 1
WQRLCUGPDYKDFJ-IZHYLOQSSA-N ethyl (3z)-3-[[3-carbamoyl-4-[(dimethylamino)methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(C)C)C(C(N)=O)=C1 WQRLCUGPDYKDFJ-IZHYLOQSSA-N 0.000 description 1
LMRDUCHWJWIOCU-RQZHXJHFSA-N ethyl (3z)-3-[[3-carbamoyl-4-[[2-(dimethylamino)acetyl]-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CN(C)C)C(C(N)=O)=C1 LMRDUCHWJWIOCU-RQZHXJHFSA-N 0.000 description 1
GCYBFBVHWMONRI-IZHYLOQSSA-N ethyl (3z)-3-[[3-chloro-4-[(dimethylamino)methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(C)C)C(Cl)=C1 GCYBFBVHWMONRI-IZHYLOQSSA-N 0.000 description 1
POPQNWNIUXXQCA-RQZHXJHFSA-N ethyl (3z)-3-[[3-chloro-4-[[2-(dimethylamino)acetyl]-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CN(C)C)C(Cl)=C1 POPQNWNIUXXQCA-RQZHXJHFSA-N 0.000 description 1
KEUFNMADPSPXCP-QPLCGJKRSA-N ethyl (3z)-3-[[3-cyano-4-[(dimethylamino)methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(C)C)C(C#N)=C1 KEUFNMADPSPXCP-QPLCGJKRSA-N 0.000 description 1
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
ANZDFYNJBOYQLG-IZHYLOQSSA-N ethyl (3z)-3-[[4-(1-methylimidazol-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=CN1C ANZDFYNJBOYQLG-IZHYLOQSSA-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
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
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
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
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
QHUDIXGJTODSBM-DQSJHHFOSA-N ethyl (3z)-3-[[4-(cyclohexylamino)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1NC1CCCCC1 QHUDIXGJTODSBM-DQSJHHFOSA-N 0.000 description 1
XZMSFBYAWRFVKO-RQZHXJHFSA-N ethyl (3z)-3-[[4-(diethylaminomethyl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(CC)CC)C=C1 XZMSFBYAWRFVKO-RQZHXJHFSA-N 0.000 description 1
UAHPGQHLSDDKQC-IZHYLOQSSA-N ethyl (3z)-3-[[4-(ethylaminomethyl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(CNCC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OCC)C=C2NC\1=O UAHPGQHLSDDKQC-IZHYLOQSSA-N 0.000 description 1
CGJLGJPXRMRVDR-VHXPQNKSSA-N ethyl (3z)-3-[[4-(methanesulfonamidomethyl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CNS(C)(=O)=O)C=C1 CGJLGJPXRMRVDR-VHXPQNKSSA-N 0.000 description 1
MQKCTOHUDXGOFG-RQZHXJHFSA-N ethyl (3z)-3-[[4-[(2-acetamidoacetyl)-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CNC(C)=O)C=C1 MQKCTOHUDXGOFG-RQZHXJHFSA-N 0.000 description 1
JSWBWTGNRWEANH-IZHYLOQSSA-N ethyl (3z)-3-[[4-[(2-aminoacetyl)-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=C1 JSWBWTGNRWEANH-IZHYLOQSSA-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
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
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
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
ACMBPOUTCUNNEI-QPLCGJKRSA-N ethyl (3z)-3-[[4-[1-amino-3-(methanesulfonamido)propyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(C(N)CCNS(C)(=O)=O)C=C1 ACMBPOUTCUNNEI-QPLCGJKRSA-N 0.000 description 1
DIWHRMJVZVOQMR-DQSJHHFOSA-N ethyl (3z)-3-[[4-[1-amino-4-(dimethylamino)butyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(C(N)CCCN(C)C)C=C1 DIWHRMJVZVOQMR-DQSJHHFOSA-N 0.000 description 1
LPVZNMSLQKJADJ-RQZHXJHFSA-N ethyl (3z)-3-[[4-[1-amino-4-(methanesulfonamido)butyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(C(N)CCCNS(C)(=O)=O)C=C1 LPVZNMSLQKJADJ-RQZHXJHFSA-N 0.000 description 1
LMPDBUQWXPQWRU-RQZHXJHFSA-N ethyl (3z)-3-[[4-[2-(1h-imidazol-5-yl)ethyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CCC1=CNC=N1 LMPDBUQWXPQWRU-RQZHXJHFSA-N 0.000 description 1
UHKVEGYQVGJASB-ZIADKAODSA-N ethyl (3z)-3-[[4-[2-(4-hydroxypiperidin-1-yl)ethyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CCN1CCC(O)CC1 UHKVEGYQVGJASB-ZIADKAODSA-N 0.000 description 1
PVQSVNCLFZCJRA-KARKAFJISA-N ethyl (3z)-3-[[4-[2-(dimethylamino)ethyl-(2-methoxybenzoyl)amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1N(CCN(C)C)C(=O)C1=CC=CC=C1OC PVQSVNCLFZCJRA-KARKAFJISA-N 0.000 description 1
KMSWNGUOBCAPQD-ZIADKAODSA-N ethyl (3z)-3-[[4-[2-(dimethylamino)ethyl-(2-methylpropanoyl)amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(CCN(C)C)C(=O)C(C)C)C=C1 KMSWNGUOBCAPQD-ZIADKAODSA-N 0.000 description 1
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
RTTCGZGAJZHUIX-DQSJHHFOSA-N ethyl (3z)-3-[[4-[2-(dimethylamino)ethyl-ethylsulfonylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(CCN(C)C)S(=O)(=O)CC)C=C1 RTTCGZGAJZHUIX-DQSJHHFOSA-N 0.000 description 1
AYECMIXQKVZTGO-RQZHXJHFSA-N ethyl (3z)-3-[[4-[2-(dimethylamino)ethyl-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)CCN(C)C)C=C1 AYECMIXQKVZTGO-RQZHXJHFSA-N 0.000 description 1
UCVDESGYVWSIKY-HKWRFOASSA-N ethyl (3z)-3-[[4-[2-(dimethylamino)ethyl-methylsulfonylamino]anilino]methylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C\NC1=CC=C(N(CCN(C)C)S(C)(=O)=O)C=C1 UCVDESGYVWSIKY-HKWRFOASSA-N 0.000 description 1
UXEOJRZPJFJGEN-ZIADKAODSA-N ethyl (3z)-3-[[4-[2-(dimethylamino)ethyl-propan-2-ylsulfonylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(CCN(C)C)S(=O)(=O)C(C)C)C=C1 UXEOJRZPJFJGEN-ZIADKAODSA-N 0.000 description 1
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
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
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
OKYBZVUDULWEDR-DQSJHHFOSA-N ethyl (3z)-3-[[4-[3-(dimethylamino)propyl-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)CCCN(C)C)C=C1 OKYBZVUDULWEDR-DQSJHHFOSA-N 0.000 description 1
YHIXYTDHADFYNE-DQSJHHFOSA-N ethyl (3z)-3-[[4-[3-(dimethylamino)propyl-methylsulfonylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(CCCN(C)C)S(C)(=O)=O)C=C1 YHIXYTDHADFYNE-DQSJHHFOSA-N 0.000 description 1
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
QILYYCRNPGJUOB-MVJHLKBCSA-N ethyl (3z)-3-[[4-[4-(dimethylamino)butanoyl-[2-(dimethylamino)-2-oxoethyl]amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(CC(=O)N(C)C)C(=O)CCCN(C)C)C=C1 QILYYCRNPGJUOB-MVJHLKBCSA-N 0.000 description 1
YVFLJBZTBGIMCY-QPLCGJKRSA-N ethyl (3z)-3-[[4-[[(2-amino-2-oxoethyl)-methylamino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(C)CC(N)=O)C=C1 YVFLJBZTBGIMCY-QPLCGJKRSA-N 0.000 description 1
KPLNAMNDLNVERF-DQSJHHFOSA-N ethyl (3z)-3-[[4-[[(2-ethoxy-2-oxoethyl)-methylamino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(CN(C)CC(=O)OCC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OCC)C=C2NC\1=O KPLNAMNDLNVERF-DQSJHHFOSA-N 0.000 description 1
BLZAOVRTMUHFRB-DQSJHHFOSA-N ethyl (3z)-3-[[4-[[1,3-dioxolan-2-ylmethyl(methyl)amino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CN(C)CC1OCCO1 BLZAOVRTMUHFRB-DQSJHHFOSA-N 0.000 description 1
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
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
HUJGOHAHCWRDTA-ZIADKAODSA-N ethyl (3z)-3-[[4-[[2-(dimethylamino)acetyl]-methylamino]-3-ethoxycarbonylanilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CN(C)C)C(C(=O)OCC)=C1 HUJGOHAHCWRDTA-ZIADKAODSA-N 0.000 description 1
FWVNYIJGAKFLPG-RQZHXJHFSA-N ethyl (3z)-3-[[4-[[2-(dimethylamino)acetyl]-methylamino]-3-fluoroanilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CN(C)C)C(F)=C1 FWVNYIJGAKFLPG-RQZHXJHFSA-N 0.000 description 1
BBAKZSSKRFAYHQ-DQSJHHFOSA-N ethyl (3z)-3-[[4-[[2-(dimethylamino)acetyl]-methylamino]-3-methoxyanilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CN(C)C)C(OC)=C1 BBAKZSSKRFAYHQ-DQSJHHFOSA-N 0.000 description 1
VWEFBNRKWBWVSJ-RQZHXJHFSA-N ethyl (3z)-3-[[4-[[2-(dimethylamino)acetyl]-methylamino]-3-nitroanilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CN(C)C)C([N+]([O-])=O)=C1 VWEFBNRKWBWVSJ-RQZHXJHFSA-N 0.000 description 1
SWRUJBCJOYDYCW-RQZHXJHFSA-N ethyl (3z)-3-[[4-[[2-(dimethylamino)acetyl]-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CN(C)C)C=C1 SWRUJBCJOYDYCW-RQZHXJHFSA-N 0.000 description 1
RXSMTEABPKZJSU-UYRXBGFRSA-N ethyl (3z)-3-[[4-[[2-(dimethylamino)acetyl]-methylamino]anilino]methylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C\NC1=CC=C(N(C)C(=O)CN(C)C)C=C1 RXSMTEABPKZJSU-UYRXBGFRSA-N 0.000 description 1
KLGREXUHOWSUCI-ZIADKAODSA-N ethyl (3z)-3-[[4-[[2-(dimethylamino)acetyl]-propan-2-ylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C(C)C)C(=O)CN(C)C)C=C1 KLGREXUHOWSUCI-ZIADKAODSA-N 0.000 description 1
XETGZBDAWRWVNO-DQSJHHFOSA-N ethyl (3z)-3-[[4-[[2-(dimethylamino)ethyl-methylamino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(C)CCN(C)C)C=C1 XETGZBDAWRWVNO-DQSJHHFOSA-N 0.000 description 1
NGDNHJZYQZUQFE-QPLCGJKRSA-N ethyl (3z)-3-[[4-[[2-(methanesulfonamido)acetyl]-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CNS(C)(=O)=O)C=C1 NGDNHJZYQZUQFE-QPLCGJKRSA-N 0.000 description 1
VUWZNUSAPAMEIA-RQZHXJHFSA-N ethyl (3z)-3-[[4-[[2-(methanesulfonamido)ethyl-methylamino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(C)CCNS(C)(=O)=O)C=C1 VUWZNUSAPAMEIA-RQZHXJHFSA-N 0.000 description 1
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
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
KOVXOBIYGAPUII-QPLCGJKRSA-N ethyl (3z)-3-[[4-[[2-aminoethyl(methyl)amino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(C)CCN)C=C1 KOVXOBIYGAPUII-QPLCGJKRSA-N 0.000 description 1
COIPPHYWTDFRLX-QPLCGJKRSA-N ethyl (3z)-3-[[4-[[2-hydroxyethyl(methyl)amino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(C)CCO)C=C1 COIPPHYWTDFRLX-QPLCGJKRSA-N 0.000 description 1
OEHGVRVGLUGFRP-RQZHXJHFSA-N ethyl (3z)-3-[[4-[[2-methoxyethyl(methyl)amino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(C)CCOC)C=C1 OEHGVRVGLUGFRP-RQZHXJHFSA-N 0.000 description 1
GKLZWJVAGURZJE-ZIADKAODSA-N ethyl (3z)-3-[[4-[[3-(dimethylamino)propyl-methylamino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(C)CCCN(C)C)C=C1 GKLZWJVAGURZJE-ZIADKAODSA-N 0.000 description 1
YDWTZPKQPNXBBU-ZIADKAODSA-N ethyl (3z)-3-[[4-[[3-acetamidopropyl(methyl)amino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(C)CCCNC(C)=O)C=C1 YDWTZPKQPNXBBU-ZIADKAODSA-N 0.000 description 1
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
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
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
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
ZKQOGXXXRNWYQT-DQSJHHFOSA-N ethyl (3z)-3-[[4-[acetyl-[2-(dimethylamino)ethyl]amino]-3-aminoanilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(CCN(C)C)C(C)=O)C(N)=C1 ZKQOGXXXRNWYQT-DQSJHHFOSA-N 0.000 description 1
BGMXTAOGVWVFPK-DQSJHHFOSA-N ethyl (3z)-3-[[4-[acetyl-[2-(dimethylamino)ethyl]amino]-3-bromoanilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(CCN(C)C)C(C)=O)C(Br)=C1 BGMXTAOGVWVFPK-DQSJHHFOSA-N 0.000 description 1
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
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
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
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
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
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
OYHYOARTJMKBTC-QPLCGJKRSA-N ethyl (3z)-3-[[4-[methylsulfonyl-[3-[(2,2,2-trifluoroacetyl)amino]propyl]amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OCC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(CCCNC(=O)C(F)(F)F)S(C)(=O)=O)C=C1 OYHYOARTJMKBTC-QPLCGJKRSA-N 0.000 description 1
LLEFRDNBMHFGLX-UHFFFAOYSA-N ethyl 1-(4-amino-n-methylanilino)piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1N(C)C1=CC=C(N)C=C1 LLEFRDNBMHFGLX-UHFFFAOYSA-N 0.000 description 1
UVUDNJXFMOTJFN-UHFFFAOYSA-N ethyl 1-[(4-aminophenyl)methyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1CC1=CC=C(N)C=C1 UVUDNJXFMOTJFN-UHFFFAOYSA-N 0.000 description 1
NRGBVJPPBFDBRV-UHFFFAOYSA-N ethyl 1-[(4-nitrophenyl)methyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1CC1=CC=C([N+]([O-])=O)C=C1 NRGBVJPPBFDBRV-UHFFFAOYSA-N 0.000 description 1
NUVTZODSNKIACW-UHFFFAOYSA-N ethyl 2-[[5-[4-(1,3-benzodioxol-5-ylamino)phthalazin-1-yl]-2-methylphenyl]sulfonylamino]acetate Chemical compound C1=C(C)C(S(=O)(=O)NCC(=O)OCC)=CC(C=2C3=CC=CC=C3C(NC=3C=C4OCOC4=CC=3)=NN=2)=C1 NUVTZODSNKIACW-UHFFFAOYSA-N 0.000 description 1
MHZBFRDOUGJKFL-UHFFFAOYSA-N ethyl 2-[methyl-[(4-nitrophenyl)methyl]amino]acetate Chemical compound CCOC(=O)CN(C)CC1=CC=C([N+]([O-])=O)C=C1 MHZBFRDOUGJKFL-UHFFFAOYSA-N 0.000 description 1
RNSNPSMLRZWYGB-UHFFFAOYSA-N ethyl 2-oxo-3h-indole-1-carboxylate Chemical compound C1=CC=C2N(C(=O)OCC)C(=O)CC2=C1 RNSNPSMLRZWYGB-UHFFFAOYSA-N 0.000 description 1
WWTYMHANUAWVMT-DQRAZIAOSA-N ethyl 4-[[(z)-(6-carbamoyl-2-oxo-1h-indol-3-ylidene)-phenylmethyl]amino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(N)=O)C=C2NC\1=O WWTYMHANUAWVMT-DQRAZIAOSA-N 0.000 description 1
208000030533 eye disease Diseases 0.000 description 1
230000003176 fibrotic effect Effects 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
208000005017 glioblastoma Diseases 0.000 description 1
239000004220 glutamic acid Substances 0.000 description 1
235000013922 glutamic acid Nutrition 0.000 description 1
239000003102 growth factor Substances 0.000 description 1
239000001963 growth medium Substances 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
229940116364 hard fat Drugs 0.000 description 1
201000003911 head and neck carcinoma Diseases 0.000 description 1
230000002489 hematologic effect Effects 0.000 description 1
239000003667 hormone antagonist Substances 0.000 description 1
102000058223 human VEGFA Human genes 0.000 description 1
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
238000003780 insertion Methods 0.000 description 1
230000037431 insertion Effects 0.000 description 1
229940047124 interferons Drugs 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
208000017169 kidney disease Diseases 0.000 description 1
229940043355 kinase inhibitor Drugs 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
229960004873 levomenthol Drugs 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
201000005202 lung cancer Diseases 0.000 description 1
208000020816 lung neoplasm Diseases 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229940057948 magnesium stearate Drugs 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
230000003211 malignant effect Effects 0.000 description 1
229960002510 mandelic acid Drugs 0.000 description 1
229940126601 medicinal product Drugs 0.000 description 1
239000002609 medium Substances 0.000 description 1
201000001441 melanoma Diseases 0.000 description 1
239000000155 melt Substances 0.000 description 1
210000003584 mesangial cell Anatomy 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
230000009401 metastasis Effects 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
HBHHTUPXRIAZAE-VLGSPTGOSA-N methyl (3z)-2-oxo-3-[1-[4-(2h-tetrazol-5-yl)anilino]butylidene]-1h-indole-6-carboxylate Chemical compound O=C/1NC2=CC(C(=O)OC)=CC=C2C\1=C(/CCC)NC(C=C1)=CC=C1C1=NN=NN1 HBHHTUPXRIAZAE-VLGSPTGOSA-N 0.000 description 1
UATXNAGHLAANAB-YBEGLDIGSA-N methyl (3z)-2-oxo-3-[1-[4-(2h-tetrazol-5-yl)anilino]ethylidene]-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(/C)NC(C=C1)=CC=C1C1=NN=NN1 UATXNAGHLAANAB-YBEGLDIGSA-N 0.000 description 1
FRRZVDUVJQJQAY-ICFOKQHNSA-N methyl (3z)-2-oxo-3-[1-[4-(2h-tetrazol-5-yl)anilino]propylidene]-1h-indole-6-carboxylate Chemical compound O=C/1NC2=CC(C(=O)OC)=CC=C2C\1=C(/CC)NC(C=C1)=CC=C1C1=NN=NN1 FRRZVDUVJQJQAY-ICFOKQHNSA-N 0.000 description 1
WNHGOWCEZGPKCM-JWGURIENSA-N methyl (3z)-2-oxo-3-[1-[4-(piperidin-1-ylmethyl)anilino]ethylidene]-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(/C)NC(C=C1)=CC=C1CN1CCCCC1 WNHGOWCEZGPKCM-JWGURIENSA-N 0.000 description 1
MILPOVQHFLFZLJ-LNVKXUELSA-N methyl (3z)-2-oxo-3-[1-[4-(piperidin-1-ylmethyl)anilino]propylidene]-1h-indole-6-carboxylate Chemical compound O=C/1NC2=CC(C(=O)OC)=CC=C2C\1=C(/CC)NC(C=C1)=CC=C1CN1CCCCC1 MILPOVQHFLFZLJ-LNVKXUELSA-N 0.000 description 1
JQSVEWLFMVTAGS-ZROIWOOFSA-N methyl (3z)-2-oxo-3-[[4-(2h-tetrazol-5-yl)anilino]methylidene]-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C\NC(C=C1)=CC=C1C1=NN=NN1 JQSVEWLFMVTAGS-ZROIWOOFSA-N 0.000 description 1
LNJSJWOCLRJVIA-ZHZULCJRSA-N methyl (3z)-2-oxo-3-[[4-(piperidin-1-ylmethyl)anilino]methylidene]-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C\NC(C=C1)=CC=C1CN1CCCCC1 LNJSJWOCLRJVIA-ZHZULCJRSA-N 0.000 description 1
KHEQXLHVUPKNQU-QPLCGJKRSA-N methyl (3z)-2-oxo-3-[[4-[(1-oxo-1,4-thiazinan-4-yl)methyl]anilino]-phenylmethylidene]-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CN1CCS(=O)CC1 KHEQXLHVUPKNQU-QPLCGJKRSA-N 0.000 description 1
FQRRZZGWVKENKU-QPLCGJKRSA-N methyl (3z)-2-oxo-3-[[4-[(3-oxopiperazin-1-yl)methyl]anilino]-phenylmethylidene]-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CN1CCNC(=O)C1 FQRRZZGWVKENKU-QPLCGJKRSA-N 0.000 description 1
NHKGMLKDGQJHNN-QPLCGJKRSA-N methyl (3z)-2-oxo-3-[phenyl-(4-pyridin-2-ylanilino)methylidene]-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1C1=CC=CC=N1 NHKGMLKDGQJHNN-QPLCGJKRSA-N 0.000 description 1
QDSBLMNXFRUSAC-QPLCGJKRSA-N methyl (3z)-2-oxo-3-[phenyl-(4-pyridin-3-ylanilino)methylidene]-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1C1=CC=CN=C1 QDSBLMNXFRUSAC-QPLCGJKRSA-N 0.000 description 1
PHIGDVCYFZLICL-VHXPQNKSSA-N methyl (3z)-2-oxo-3-[phenyl-[4-(1,2,4-triazol-1-ylmethyl)anilino]methylidene]-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CN1C=NC=N1 PHIGDVCYFZLICL-VHXPQNKSSA-N 0.000 description 1
IQEQBXQGCPVPOO-DQSJHHFOSA-N methyl (3z)-2-oxo-3-[phenyl-[4-(2-piperidin-1-ylethyl)anilino]methylidene]-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CCN1CCCCC1 IQEQBXQGCPVPOO-DQSJHHFOSA-N 0.000 description 1
UNEIROSAOKXQCW-MRCUWXFGSA-N methyl (3z)-2-oxo-3-[phenyl-[4-(2h-tetrazol-5-yl)anilino]methylidene]-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1C1=NN=NN1 UNEIROSAOKXQCW-MRCUWXFGSA-N 0.000 description 1
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
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
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
PSBOWDCVRMIKJN-KQWNVCNZSA-N methyl (3z)-3-[1-[4-[acetyl-[3-(dimethylamino)propyl]amino]anilino]ethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(/C)NC1=CC=C(N(CCCN(C)C)C(C)=O)C=C1 PSBOWDCVRMIKJN-KQWNVCNZSA-N 0.000 description 1
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
GJZOCJMBIIKQIK-DQSJHHFOSA-N methyl (3z)-3-[[3-acetamido-4-[[2-(dimethylamino)acetyl]-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CN(C)C)C(NC(C)=O)=C1 GJZOCJMBIIKQIK-DQSJHHFOSA-N 0.000 description 1
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
MDHPVJCMQBSWTC-QPLCGJKRSA-N methyl (3z)-3-[[3-bromo-4-[[2-(dimethylamino)acetyl]-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CN(C)C)C(Br)=C1 MDHPVJCMQBSWTC-QPLCGJKRSA-N 0.000 description 1
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
LITNYBZNPBBUDL-RQZHXJHFSA-N methyl (3z)-3-[[3-cyano-4-[[2-(dimethylamino)acetyl]-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CN(C)C)C(C#N)=C1 LITNYBZNPBBUDL-RQZHXJHFSA-N 0.000 description 1
CSMAMMGWSPPCFM-VHXPQNKSSA-N methyl (3z)-3-[[4-(1,3-diaminopropyl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(C(N)CCN)C=C1 CSMAMMGWSPPCFM-VHXPQNKSSA-N 0.000 description 1
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
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
DOOGGJTZJJJMTJ-FCQUAONHSA-N methyl (3z)-3-[[4-(2-amino-2-oxoethyl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CC(N)=O)C=C1 DOOGGJTZJJJMTJ-FCQUAONHSA-N 0.000 description 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
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
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
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
XHYDNVCBHSFLQR-FCQUAONHSA-N methyl (3z)-3-[[4-(methanesulfonamidomethyl)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CNS(C)(=O)=O)C=C1 XHYDNVCBHSFLQR-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
MFMREZXKGGWAGY-FCQUAONHSA-N methyl (3z)-3-[[4-[(2,5-dioxoimidazolidin-4-yl)methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CC1NC(=O)NC1=O MFMREZXKGGWAGY-FCQUAONHSA-N 0.000 description 1
URNUEBLYEXQFTO-WVVAYPLRSA-N methyl (3z)-3-[[4-[(2,5-dioxoimidazolidin-4-ylidene)methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1C=C1NC(=O)NC1=O URNUEBLYEXQFTO-WVVAYPLRSA-N 0.000 description 1
XBUCECOAKVVLNR-ZIADKAODSA-N methyl (3z)-3-[[4-[(2,6-dimethylpiperidin-1-yl)methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CN1C(C)CCCC1C XBUCECOAKVVLNR-ZIADKAODSA-N 0.000 description 1
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
ZUWLEBRSSYJVEQ-VHXPQNKSSA-N methyl (3z)-3-[[4-[(2-aminoacetyl)-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CN)C=C1 ZUWLEBRSSYJVEQ-VHXPQNKSSA-N 0.000 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
RTBGMEMZIPGYHB-MVJHLKBCSA-N methyl (3z)-3-[[4-[(4-benzoylpiperazin-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=C1CN(CC1)CCN1C(=O)C1=CC=CC=C1 RTBGMEMZIPGYHB-MVJHLKBCSA-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
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
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
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
IZTCGPDAIPBHGU-BOPFTXTBSA-N methyl (3z)-3-[[4-[(dimethylamino)methyl]anilino]methylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C\NC1=CC=C(CN(C)C)C=C1 IZTCGPDAIPBHGU-BOPFTXTBSA-N 0.000 description 1
RPPPXRUSARQHLC-DQSJHHFOSA-N methyl (3z)-3-[[4-[(dipropylamino)methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(CN(CCC)CCC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O RPPPXRUSARQHLC-DQSJHHFOSA-N 0.000 description 1
POJVTYBLLXHLQL-QPLCGJKRSA-N methyl (3z)-3-[[4-[1-amino-3-(dimethylamino)propyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(C(N)CCN(C)C)C=C1 POJVTYBLLXHLQL-QPLCGJKRSA-N 0.000 description 1
ZLYZTANYDSIYPC-IZHYLOQSSA-N methyl (3z)-3-[[4-[1-amino-3-(methanesulfonamido)propyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(C(N)CCNS(C)(=O)=O)C=C1 ZLYZTANYDSIYPC-IZHYLOQSSA-N 0.000 description 1
BTHGXGDWQASQRP-RQZHXJHFSA-N methyl (3z)-3-[[4-[1-amino-4-(dimethylamino)butyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(C(N)CCCN(C)C)C=C1 BTHGXGDWQASQRP-RQZHXJHFSA-N 0.000 description 1
VWANDBSUBUHNFW-QPLCGJKRSA-N methyl (3z)-3-[[4-[1-amino-4-(methanesulfonamido)butyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(C(N)CCCNS(C)(=O)=O)C=C1 VWANDBSUBUHNFW-QPLCGJKRSA-N 0.000 description 1
ZYKDYALDSSSEKC-QPLCGJKRSA-N methyl (3z)-3-[[4-[2-(1h-imidazol-5-yl)ethyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CCC1=CNC=N1 ZYKDYALDSSSEKC-QPLCGJKRSA-N 0.000 description 1
QXRQSNFYTPRXMN-DQSJHHFOSA-N methyl (3z)-3-[[4-[2-(4-hydroxypiperidin-1-yl)ethyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CCN1CCC(O)CC1 QXRQSNFYTPRXMN-DQSJHHFOSA-N 0.000 description 1
ZBGGFGDKVXCEJA-DQSJHHFOSA-N methyl (3z)-3-[[4-[2-(diethylamino)ethyl-methylsulfonylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(CCN(CC)CC)S(C)(=O)=O)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O ZBGGFGDKVXCEJA-DQSJHHFOSA-N 0.000 description 1
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
UDRYCALAFSXOJU-IZHYLOQSSA-N methyl (3z)-3-[[4-[2-(dimethylamino)ethoxy]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(OCCN(C)C)C=C1 UDRYCALAFSXOJU-IZHYLOQSSA-N 0.000 description 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
UXPGGJLMVUQWLH-FLWNBWAVSA-N methyl (3z)-3-[[4-[2-(dimethylamino)ethyl-(pyridine-3-carbonyl)amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1N(CCN(C)C)C(=O)C1=CC=CN=C1 UXPGGJLMVUQWLH-FLWNBWAVSA-N 0.000 description 1
UTISDSYHQVSJSO-RQZHXJHFSA-N methyl (3z)-3-[[4-[2-(dimethylamino)ethyl-ethylsulfonylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(CCN(C)C)S(=O)(=O)CC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O UTISDSYHQVSJSO-RQZHXJHFSA-N 0.000 description 1
NSJWGYJIQYLIMC-QPLCGJKRSA-N methyl (3z)-3-[[4-[2-(dimethylamino)ethyl-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)CCN(C)C)C=C1 NSJWGYJIQYLIMC-QPLCGJKRSA-N 0.000 description 1
WJZTXYKYCJDGGW-DQSJHHFOSA-N methyl (3z)-3-[[4-[2-(dimethylamino)ethyl-propanoylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(CCN(C)C)C(=O)CC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O WJZTXYKYCJDGGW-DQSJHHFOSA-N 0.000 description 1
AGQVXLYIQBWXIE-DQSJHHFOSA-N methyl (3z)-3-[[4-[2-(dimethylamino)ethyl-propylsulfonylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(CCN(C)C)S(=O)(=O)CCC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O AGQVXLYIQBWXIE-DQSJHHFOSA-N 0.000 description 1
XNJPIGSAHQKNRZ-QPLCGJKRSA-N methyl (3z)-3-[[4-[2-(ethylamino)ethyl-methylsulfonylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(CCNCC)S(C)(=O)=O)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O XNJPIGSAHQKNRZ-QPLCGJKRSA-N 0.000 description 1
HUKMKKIFMCLRLL-IZHYLOQSSA-N methyl (3z)-3-[[4-[2-(methylamino)ethyl-methylsulfonylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(CCNC)S(C)(=O)=O)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O HUKMKKIFMCLRLL-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
JLDXMMDMAJYUIJ-VHXPQNKSSA-N methyl (3z)-3-[[4-[2-aminoethyl(methylsulfonyl)amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(CCN)S(C)(=O)=O)C=C1 JLDXMMDMAJYUIJ-VHXPQNKSSA-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
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
QTEFTUGUGQMXBI-QPLCGJKRSA-N methyl (3z)-3-[[4-[3-(methylamino)propyl-methylsulfonylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(CCCNC)S(C)(=O)=O)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O QTEFTUGUGQMXBI-QPLCGJKRSA-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
BTUACWQNCVFDMG-DQSJHHFOSA-N methyl (3z)-3-[[4-[[2-(diethylamino)-2-oxoethyl]-methylsulfonylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(CC(=O)N(CC)CC)S(C)(=O)=O)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O BTUACWQNCVFDMG-DQSJHHFOSA-N 0.000 description 1
BAUFJTXWLJKPAR-DQSJHHFOSA-N methyl (3z)-3-[[4-[[2-(diethylamino)acetyl]-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(C)C(=O)CN(CC)CC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O BAUFJTXWLJKPAR-DQSJHHFOSA-N 0.000 description 1
LGPFPZWGWQZVGL-FLWNBWAVSA-N methyl (3z)-3-[[4-[[2-(dimethylamino)-2-oxoethyl]-[3-(dimethylamino)propylsulfonyl]amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(CC(=O)N(C)C)S(=O)(=O)CCCN(C)C)C=C1 LGPFPZWGWQZVGL-FLWNBWAVSA-N 0.000 description 1
RXHZDTGOOZYYRM-DQSJHHFOSA-N methyl (3z)-3-[[4-[[2-(dimethylamino)-2-oxoethyl]-propanoylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(CC(=O)N(C)C)C(=O)CC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O RXHZDTGOOZYYRM-DQSJHHFOSA-N 0.000 description 1
VJLJKPGFMIFONZ-RQZHXJHFSA-N methyl (3z)-3-[[4-[[2-(dimethylamino)acetyl]-ethylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(C(=O)CN(C)C)CC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O VJLJKPGFMIFONZ-RQZHXJHFSA-N 0.000 description 1
HOXJEHKBYSZHDT-RQZHXJHFSA-N methyl (3z)-3-[[4-[[2-(dimethylamino)acetyl]-methylamino]-3-(methanesulfonamido)anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CN(C)C)C(NS(C)(=O)=O)=C1 HOXJEHKBYSZHDT-RQZHXJHFSA-N 0.000 description 1
WAUCSJCPUORSTC-QPLCGJKRSA-N methyl (3z)-3-[[4-[[2-(dimethylamino)acetyl]-methylamino]-3-fluoroanilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CN(C)C)C(F)=C1 WAUCSJCPUORSTC-QPLCGJKRSA-N 0.000 description 1
HQGFACIJAOUSHR-QPLCGJKRSA-N methyl (3z)-3-[[4-[[2-(dimethylamino)acetyl]-methylamino]-3-hydroxyanilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CN(C)C)C(O)=C1 HQGFACIJAOUSHR-QPLCGJKRSA-N 0.000 description 1
KKQAKFFHVQJBRP-RQZHXJHFSA-N methyl (3z)-3-[[4-[[2-(dimethylamino)acetyl]-methylamino]-3-methylanilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CN(C)C)C(C)=C1 KKQAKFFHVQJBRP-RQZHXJHFSA-N 0.000 description 1
WZSPHJSIBQNMLK-QPLCGJKRSA-N methyl (3z)-3-[[4-[[2-(dimethylamino)acetyl]-methylamino]-3-nitroanilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CN(C)C)C([N+]([O-])=O)=C1 WZSPHJSIBQNMLK-QPLCGJKRSA-N 0.000 description 1
WDLKBZLGTNDINZ-PDGQHHTCSA-N methyl (3z)-3-[[4-[[2-(dimethylamino)acetyl]-methylamino]anilino]methylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C\NC1=CC=C(N(C)C(=O)CN(C)C)C=C1 WDLKBZLGTNDINZ-PDGQHHTCSA-N 0.000 description 1
FVQJAAAWWIGEMK-DQSJHHFOSA-N methyl (3z)-3-[[4-[[2-(dimethylamino)acetyl]-propylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(C(=O)CN(C)C)CCC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O FVQJAAAWWIGEMK-DQSJHHFOSA-N 0.000 description 1
CLMURYIACIHACU-RQZHXJHFSA-N methyl (3z)-3-[[4-[[2-(dimethylamino)ethyl-methylamino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(C)CCN(C)C)C=C1 CLMURYIACIHACU-RQZHXJHFSA-N 0.000 description 1
CXDYWQZLHPBBQY-QPLCGJKRSA-N methyl (3z)-3-[[4-[[2-(ethylamino)-2-oxoethyl]-methylsulfonylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(CC(=O)NCC)S(C)(=O)=O)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O CXDYWQZLHPBBQY-QPLCGJKRSA-N 0.000 description 1
OEYMBRUKBJIOJL-QPLCGJKRSA-N methyl (3z)-3-[[4-[[2-(ethylamino)acetyl]-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(C)C(=O)CNCC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O OEYMBRUKBJIOJL-QPLCGJKRSA-N 0.000 description 1
RTXFTXQHTXRSSM-IZHYLOQSSA-N methyl (3z)-3-[[4-[[2-(methanesulfonamido)acetyl]-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CNS(C)(=O)=O)C=C1 RTXFTXQHTXRSSM-IZHYLOQSSA-N 0.000 description 1
TXANJRRNRHLIGN-QPLCGJKRSA-N methyl (3z)-3-[[4-[[2-(methanesulfonamido)ethyl-methylamino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(C)CCNS(C)(=O)=O)C=C1 TXANJRRNRHLIGN-QPLCGJKRSA-N 0.000 description 1
WZOBASBNPSNEQM-IZHYLOQSSA-N methyl (3z)-3-[[4-[[2-(methylamino)-2-oxoethyl]-methylsulfonylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(CC(=O)NC)S(C)(=O)=O)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O WZOBASBNPSNEQM-IZHYLOQSSA-N 0.000 description 1
USVLUTIAGKLFLC-RQZHXJHFSA-N methyl (3z)-3-[[4-[[2-[(2-amino-2-oxoethyl)-methylamino]acetyl]-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CN(C)CC(N)=O)C=C1 USVLUTIAGKLFLC-RQZHXJHFSA-N 0.000 description 1
LLRYASAHXGEORL-ZIADKAODSA-N methyl (3z)-3-[[4-[[2-[2-(dimethylamino)ethyl-methylamino]acetyl]-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CN(C)CCN(C)C)C=C1 LLRYASAHXGEORL-ZIADKAODSA-N 0.000 description 1
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
RZNYISXKOSUPRU-DQSJHHFOSA-N methyl (3z)-3-[[4-[[2-[bis(2-hydroxyethyl)amino]acetyl]-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)C(=O)CN(CCO)CCO)C=C1 RZNYISXKOSUPRU-DQSJHHFOSA-N 0.000 description 1
XTHMDGVWHHKQOE-RQZHXJHFSA-N methyl (3z)-3-[[4-[[2-[ethyl(methyl)amino]acetyl]-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(C)C(=O)CN(C)CC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O XTHMDGVWHHKQOE-RQZHXJHFSA-N 0.000 description 1
GCSYCCHPGMVUKA-ZIADKAODSA-N methyl (3z)-3-[[4-[[2-[ethyl(propyl)amino]acetyl]-methylamino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(C)C(=O)CN(CC)CCC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O GCSYCCHPGMVUKA-ZIADKAODSA-N 0.000 description 1
FKSICKKKGOVLIS-RQZHXJHFSA-N methyl (3z)-3-[[4-[[2-acetamidoethyl(methyl)amino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(CN(C)CCNC(C)=O)C=C1 FKSICKKKGOVLIS-RQZHXJHFSA-N 0.000 description 1
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
RXZWGNDZZXCZGH-DQSJHHFOSA-N methyl (3z)-3-[[4-[[3-acetamidopropyl(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)CCCNC(C)=O)C=C1 RXZWGNDZZXCZGH-DQSJHHFOSA-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
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
AOUHPEGJMFYYFU-RQZHXJHFSA-N methyl (3z)-3-[[4-[[ethyl(propyl)amino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(CN(CC)CCC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O AOUHPEGJMFYYFU-RQZHXJHFSA-N 0.000 description 1
YMPRIZDZHDMBLD-ZIADKAODSA-N methyl (3z)-3-[[4-[[hexyl(methyl)amino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(CN(C)CCCCCC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O YMPRIZDZHDMBLD-ZIADKAODSA-N 0.000 description 1
OULCGLUBKXTBRA-KTMFPKCZSA-N methyl (3z)-3-[[4-[[methyl(2-phenylethyl)amino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1CN(C)CCC1=CC=CC=C1 OULCGLUBKXTBRA-KTMFPKCZSA-N 0.000 description 1
VAIRUXVDRLLXEU-QPLCGJKRSA-N methyl (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)OC)C=C2NC\1=O VAIRUXVDRLLXEU-QPLCGJKRSA-N 0.000 description 1
PJHMTIYWQHYUSZ-QPLCGJKRSA-N methyl (3z)-3-[[4-[[methyl-[2-(methylamino)-2-oxoethyl]amino]methyl]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(CN(C)CC(=O)NC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O PJHMTIYWQHYUSZ-QPLCGJKRSA-N 0.000 description 1
LGYZWMSAASYNAN-IZHYLOQSSA-N methyl (3z)-3-[[4-[acetyl(2-aminoethyl)amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(CCN)C(C)=O)C=C1 LGYZWMSAASYNAN-IZHYLOQSSA-N 0.000 description 1
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
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
IZTXKRFGALXQFK-KTMFPKCZSA-N methyl (3z)-3-[[4-[benzenesulfonyl-[2-(dimethylamino)ethyl]amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1N(CCN(C)C)S(=O)(=O)C1=CC=CC=C1 IZTXKRFGALXQFK-KTMFPKCZSA-N 0.000 description 1
INOGNMCSLFRZAV-KTMFPKCZSA-N methyl (3z)-3-[[4-[benzoyl-[2-(dimethylamino)ethyl]amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1N(CCN(C)C)C(=O)C1=CC=CC=C1 INOGNMCSLFRZAV-KTMFPKCZSA-N 0.000 description 1
KNAYESYOVINZLR-KNWKATPGSA-N methyl (3z)-3-[[4-[benzyl-(2-piperidin-1-ylacetyl)amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1N(C(=O)CN1CCCCC1)CC1=CC=CC=C1 KNAYESYOVINZLR-KNWKATPGSA-N 0.000 description 1
RZRQHIPUCVMBGN-DTTHWBISSA-N methyl (3z)-3-[[4-[benzyl-[2-[benzyl(methyl)amino]acetyl]amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1N(C(=O)CN(C)CC=1C=CC=CC=1)CC1=CC=CC=C1 RZRQHIPUCVMBGN-DTTHWBISSA-N 0.000 description 1
RWLCROIPWSUHJF-ZIADKAODSA-N methyl (3z)-3-[[4-[butyl-[2-(dimethylamino)acetyl]amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(C(=O)CN(C)C)CCCC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O RWLCROIPWSUHJF-ZIADKAODSA-N 0.000 description 1
AAEHNSZVCCLBDC-ZIADKAODSA-N methyl (3z)-3-[[4-[butylsulfonyl-[2-(dimethylamino)ethyl]amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(CCN(C)C)S(=O)(=O)CCCC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O AAEHNSZVCCLBDC-ZIADKAODSA-N 0.000 description 1
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
UEIQMVYRNFWKTR-FCQUAONHSA-N methyl (3z)-3-[[4-[methyl(methylsulfonyl)amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(C)S(C)(=O)=O)C=C1 UEIQMVYRNFWKTR-FCQUAONHSA-N 0.000 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
STMBVXYQKYKAOW-DQSJHHFOSA-N methyl (3z)-3-[[4-[methyl-(2-piperazin-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)CN1CCNCC1 STMBVXYQKYKAOW-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
CKSHKSLNZDHHFF-IZHYLOQSSA-N methyl (3z)-3-[[4-[methyl-[2-(methylamino)acetyl]amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(N(C)C(=O)CNC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O CKSHKSLNZDHHFF-IZHYLOQSSA-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
XSPAJBFOMCBXQS-QPLCGJKRSA-N methyl (3z)-3-[[4-[methyl-[3-(methylamino)propanoyl]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 XSPAJBFOMCBXQS-QPLCGJKRSA-N 0.000 description 1
VPJPIDGNIJXAFS-ZIADKAODSA-N methyl (3z)-3-[[4-[methylsulfonyl(2-piperidin-1-ylethyl)amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1N(S(C)(=O)=O)CCN1CCCCC1 VPJPIDGNIJXAFS-ZIADKAODSA-N 0.000 description 1
LPFSELPFSKESFN-DQSJHHFOSA-N methyl (3z)-3-[[4-[methylsulfonyl(2-pyrrolidin-1-ylethyl)amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1N(S(C)(=O)=O)CCN1CCCC1 LPFSELPFSKESFN-DQSJHHFOSA-N 0.000 description 1
GAPKEPIGKOPJOC-DQSJHHFOSA-N methyl (3z)-3-[[4-[methylsulfonyl-(2-morpholin-4-yl-2-oxoethyl)amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1N(S(C)(=O)=O)CC(=O)N1CCOCC1 GAPKEPIGKOPJOC-DQSJHHFOSA-N 0.000 description 1
CFSALSHJYOGOLL-DQSJHHFOSA-N methyl (3z)-3-[[4-[methylsulfonyl-(2-oxo-2-pyrrolidin-1-ylethyl)amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC(C=C1)=CC=C1N(S(C)(=O)=O)CC(=O)N1CCCC1 CFSALSHJYOGOLL-DQSJHHFOSA-N 0.000 description 1
ZHKJEDPUXSVIFH-IZHYLOQSSA-N methyl (3z)-3-[[4-[methylsulfonyl-[3-[(2,2,2-trifluoroacetyl)amino]propyl]amino]anilino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=C(N(CCCNC(=O)C(F)(F)F)S(C)(=O)=O)C=C1 ZHKJEDPUXSVIFH-IZHYLOQSSA-N 0.000 description 1
VXYDONSUAPNUAL-MRCUWXFGSA-N methyl (3z)-3-[[methyl(piperidin-4-yl)amino]-phenylmethylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\N(C)C1CCNCC1 VXYDONSUAPNUAL-MRCUWXFGSA-N 0.000 description 1
ILLAFQLVCWQSQA-MRCUWXFGSA-N methyl (3z)-3-[anilino(phenyl)methylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=CC=CC=1)\NC1=CC=CC=C1 ILLAFQLVCWQSQA-MRCUWXFGSA-N 0.000 description 1
YLFLCTBGQLPNCU-UHFFFAOYSA-N methyl 2-(2-methoxy-2-oxoethyl)-5-nitrobenzoate Chemical compound COC(=O)CC1=CC=C([N+]([O-])=O)C=C1C(=O)OC YLFLCTBGQLPNCU-UHFFFAOYSA-N 0.000 description 1
QUOAYJYCXJEUSP-UHFFFAOYSA-N methyl 2-[(4-nitrophenyl)methylamino]acetate Chemical compound COC(=O)CNCC1=CC=C([N+]([O-])=O)C=C1 QUOAYJYCXJEUSP-UHFFFAOYSA-N 0.000 description 1
QABLOFMHHSOFRJ-UHFFFAOYSA-N methyl 2-chloroacetate Chemical compound COC(=O)CCl QABLOFMHHSOFRJ-UHFFFAOYSA-N 0.000 description 1
SHWVZUGUOIRBTR-UHFFFAOYSA-N methyl 2-hydroxy-3-[N-[4-[(2-oxopyrrolidin-1-yl)methyl]phenyl]-C-phenylcarbonimidoyl]-1H-indole-6-carboxylate Chemical compound COC(=O)C1=CC2=C(C=C1)C(=C(N2)O)C(=NC3=CC=C(C=C3)CN4CCCC4=O)C5=CC=CC=C5 SHWVZUGUOIRBTR-UHFFFAOYSA-N 0.000 description 1
YUGAQWBIOKQVPV-UHFFFAOYSA-N methyl 3-[N-[4-[acetyl-[3-(dimethylamino)propyl]amino]phenyl]-C-phenylcarbonimidoyl]-2-hydroxy-1H-indole-6-carboxylate Chemical compound CC(=O)N(CCCN(C)C)C1=CC=C(C=C1)N=C(C2=CC=CC=C2)C3=C(NC4=C3C=CC(=C4)C(=O)OC)O YUGAQWBIOKQVPV-UHFFFAOYSA-N 0.000 description 1
FPUPGTDVGVCPMU-DCXSSQDFSA-N methyl 3-amino-3-[4-[[(z)-(6-carbamoyl-2-oxo-1h-indol-3-ylidene)-phenylmethyl]amino]phenyl]propanoate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(C(N)CC(=O)OC)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=C(C(N)=O)C=C2NC\1=O FPUPGTDVGVCPMU-DCXSSQDFSA-N 0.000 description 1
AXLYJLKKPUICKV-UHFFFAOYSA-N methyl 3-nitrobenzoate Chemical compound COC(=O)C1=CC=CC([N+]([O-])=O)=C1 AXLYJLKKPUICKV-UHFFFAOYSA-N 0.000 description 1
DCDSLKRPXTVJSA-UHFFFAOYSA-N methyl 4-(2-methoxy-2-oxoethyl)-3-nitrobenzoate Chemical compound COC(=O)CC1=CC=C(C(=O)OC)C=C1[N+]([O-])=O DCDSLKRPXTVJSA-UHFFFAOYSA-N 0.000 description 1
VQRGPGOMRCYILE-VLGSPTGOSA-N methyl 4-[[(1z)-1-(6-carbamoyl-2-oxo-1h-indol-3-ylidene)butyl]amino]benzoate Chemical compound O=C/1NC2=CC(C(N)=O)=CC=C2C\1=C(/CCC)NC1=CC=C(C(=O)OC)C=C1 VQRGPGOMRCYILE-VLGSPTGOSA-N 0.000 description 1
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- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
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NO20021719A 1999-10-13 2002-04-11 Indoliner, substituert i 6-stilling, og farmasoytisk preparat, samt anvendelse og fremstilling derav. NO322746B1 (no)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE19949208A DE19949208A1 (de)	1999-10-13	1999-10-13	In 6-Stellung substituierte Indolinone, ihre Herstellung und ihre Verwendung als Arzneimittel
DE2000142696 DE10042696A1 (de)	2000-08-31	2000-08-31	In 6-Stellung substituierte Indolinone, ihre Herstellung und ihre Verwendung als Arzneimittel
PCT/EP2000/009867 WO2001027081A1 (fr)	1999-10-13	2000-10-09	Indolinones substituees en position 6, leur preparation et leur utilisation en tant que medicaments

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NO20021719A NO322746B1 (no)	1999-10-13	2002-04-11	Indoliner, substituert i 6-stilling, og farmasoytisk preparat, samt anvendelse og fremstilling derav.
NO2015009C NO2015009I1 (no)	1999-10-13	2015-03-18	Nintedanib, tautomere og salter derav, spesielt Nintedanib og fysiologiske akseptable salter derav, spesielt Nintedanib esilat; 3-Z-[l-(4-(N-((4-metylpiperazin-1-yl)-metylkarbonyl)-N-metylamino)- anilino)-1-fenylmetylen]-6-metoksykarbonyl-2-indolinon - Se blant annet kravene 1, 2, 5 (t) og 6 i basispatentet
NO2023033C NO2023033I1 (no)	1999-10-13	2023-09-05	Nintedanib

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NO2023033C NO2023033I1 (no)	1999-10-13	2023-09-05	Nintedanib

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DE19815020A1 (de) *	1998-04-03	1999-10-07	Boehringer Ingelheim Pharma	Neue substituierte Indolinone, ihre Herstellung und ihre Verwendung als Arzneimittel
DE19816624A1 (de) *	1998-04-15	1999-10-21	Boehringer Ingelheim Pharma	Neue substituierte Indolinone, ihre Herstellung und ihre Verwendung als Arzneimittel
DE19824922A1 (de)	1998-06-04	1999-12-09	Boehringer Ingelheim Pharma	Neue substituierte Indolinone, ihre Herstellung und ihre Verwendung als Arzneimittel
GB9904933D0 (en) *	1999-03-04	1999-04-28	Glaxo Group Ltd	Compounds

2000
- 2000-09-10 UA UA2002053890A patent/UA75054C2/uk unknown
- 2000-10-09 SI SI200031039T patent/SI1224170T1/sl unknown
- 2000-10-09 MX MXPA02002799A patent/MXPA02002799A/es active IP Right Grant
- 2000-10-09 BR BRPI0014735-4 patent/BRPI0014735B8/pt active IP Right Grant
- 2000-10-09 CZ CZ20021410A patent/CZ301073B6/cs unknown
- 2000-10-09 PL PL355433A patent/PL207445B1/pl not_active IP Right Cessation
- 2000-10-09 NZ NZ518489A patent/NZ518489A/en not_active IP Right Cessation
- 2000-10-09 CA CA002387013A patent/CA2387013C/fr not_active Expired - Lifetime
- 2000-10-09 CN CNB008158681A patent/CN100455568C/zh not_active Expired - Lifetime
- 2000-10-09 DE DE50015711T patent/DE50015711D1/de not_active Expired - Lifetime
- 2000-10-09 AU AU10233/01A patent/AU781939B2/en active Active
- 2000-10-09 EP EP09164507A patent/EP2157081A1/fr not_active Withdrawn
- 2000-10-09 EP EP00971347.0A patent/EP1224170B9/fr not_active Expired - Lifetime
- 2000-10-09 KR KR1020077017807A patent/KR100857734B1/ko active IP Right Grant
- 2000-10-09 JP JP2001530102A patent/JP4021664B2/ja not_active Expired - Lifetime
- 2000-10-09 KR KR1020027004701A patent/KR100835546B1/ko active IP Right Grant
- 2000-10-09 PT PT00971347T patent/PT1224170E/pt unknown
- 2000-10-09 ME MEP-454/08A patent/MEP45408A/xx unknown
- 2000-10-09 RS YUP-266/02A patent/RS51013B/sr unknown
- 2000-10-09 SK SK646-2002A patent/SK287312B6/sk not_active IP Right Cessation
- 2000-10-09 WO PCT/EP2000/009867 patent/WO2001027081A1/fr active IP Right Grant
- 2000-10-09 HU HU0204587A patent/HU230416B1/hu active Protection Beyond IP Right Term
- 2000-10-09 IL IL14875600A patent/IL148756A0/xx active IP Right Grant
- 2000-10-09 EE EEP200200197A patent/EE05427B1/xx active Protection Beyond IP Right Term
- 2000-10-09 DK DK00971347.0T patent/DK1224170T5/en active
- 2000-10-09 AT AT00971347T patent/ATE439342T1/de active
- 2000-10-09 EA EA200200380A patent/EA006080B1/ru not_active IP Right Cessation
- 2000-10-09 ES ES00971347T patent/ES2331459T3/es not_active Expired - Lifetime
- 2000-10-11 PE PE2000001088A patent/PE20010671A1/es not_active IP Right Cessation
- 2000-10-11 MY MYPI20004762A patent/MY127956A/en unknown
- 2000-10-11 EG EG2000101293A patent/EG25931A/xx active
- 2000-10-12 CO CO00077925A patent/CO5261488A1/es not_active Application Discontinuation
- 2000-10-12 TW TW089121320A patent/TWI268922B/zh active
- 2000-10-13 AR ARP000105394A patent/AR026036A1/es active Pending
2001
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2002
- 2002-03-19 IL IL148756A patent/IL148756A/en active Protection Beyond IP Right Term
- 2002-04-05 BG BG106587A patent/BG65983B1/bg active Active
- 2002-04-10 HR HR20020306A patent/HRP20020306B1/xx not_active IP Right Cessation
- 2002-04-11 NO NO20021719A patent/NO322746B1/no active Protection Beyond IP Right Term
2003
- 2003-06-30 HK HK03104649.4A patent/HK1052505B/zh not_active IP Right Cessation
2007
- 2007-08-15 JP JP2007211755A patent/JP2007302697A/ja active Pending
2009
- 2009-11-06 CY CY20091101152T patent/CY1110067T1/el unknown
2015
- 2015-03-13 CY CY2015009C patent/CY2015009I2/el unknown
- 2015-03-16 FR FR15C0024C patent/FR15C0024I2/fr active Active
- 2015-03-16 LU LU92681C patent/LU92681I2/fr unknown
- 2015-03-16 NL NL300725C patent/NL300725I2/nl unknown
- 2015-03-16 BE BE2015C018C patent/BE2015C018I2/fr unknown
- 2015-03-18 NO NO2015009C patent/NO2015009I1/no unknown
2016
- 2016-05-13 HU HUS1600022C patent/HUS1600022I1/hu unknown
2023
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Also Published As

Publication number	Publication date
PE20010671A1 (es)	2001-06-28
IL148756A0 (en)	2002-09-12
CN1391557A (zh)	2003-01-15
JP4021664B2 (ja)	2007-12-12
CO5261488A1 (es)	2003-03-31
EG25931A (en)	2012-10-24
JP2003511441A (ja)	2003-03-25
CY2015009I1 (el)	2016-12-14
JP2007302697A (ja)	2007-11-22
NO2023033I1 (no)	2023-09-05
MY127956A (en)	2007-01-31
AR026036A1 (es)	2002-12-26
BG106587A (bg)	2003-01-31
HUP0204587A2 (en)	2003-05-28
BE2015C018I2 (fr)	2019-10-23
NO2015009I1 (no)	2015-03-30
EE05427B1 (et)	2011-06-15
FR15C0024I1 (fr)	2015-04-17
RS51013B (sr)	2010-10-31
NO2015009I2 (fr)	2015-03-18
NO20021719D0 (no)	2002-04-11
YU26602A (sh)	2004-11-25
TWI268922B (en)	2006-12-21
HUS1600022I1 (hu)	2017-02-28
MXPA02002799A (es)	2003-02-27
ES2331459T3 (es)	2010-01-05
FR15C0024I2 (fr)	2016-08-26
BG65983B1 (bg)	2010-08-31
EE200200197A (et)	2003-06-16
IL148756A (en)	2007-10-31
HK1052505B (zh)	2009-06-26
CA2387013C (fr)	2009-12-29
SK287312B6 (sk)	2010-06-07
NZ518489A (en)	2005-05-27
CN100455568C (zh)	2009-01-28
BRPI0014735A (pt)	2002-07-16
WO2001027081A1 (fr)	2001-04-19
CZ20021410A3 (cs)	2002-07-17
HUP0204587A3 (en)	2004-07-28
KR100835546B1 (ko)	2008-06-09
MEP45408A (en)	2011-02-10
BRPI0014735B1 (pt)	2012-07-10
EP1224170B9 (fr)	2017-11-22
EA006080B1 (ru)	2005-08-25
CZ301073B6 (cs)	2009-10-29
AU781939B2 (en)	2005-06-23
SA01210704B1 (ar)	2006-12-05
LU92681I2 (fr)	2015-05-18
DE50015711D1 (de)	2009-09-24
SI1224170T1 (sl)	2009-12-31
NO20021719L (no)	2002-04-11
HRP20020306B1 (en)	2010-09-30
UA75054C2 (uk)	2006-03-15
HRP20020306A2 (en)	2003-10-31
EP1224170B1 (fr)	2009-08-12
NL300725I2 (nl)	2017-07-13
PT1224170E (pt)	2009-10-01
PL207445B1 (pl)	2010-12-31
LU92681I9 (fr)	2019-01-03
CY2015009I2 (el)	2016-12-14
CA2387013A1 (fr)	2001-04-19
KR100857734B1 (ko)	2008-09-10
AU1023301A (en)	2001-04-23
ATE439342T1 (de)	2009-08-15
BRPI0014735B8 (pt)	2021-07-06
EA200200380A1 (ru)	2002-10-31
KR20020038949A (ko)	2002-05-24
SK6462002A3 (en)	2002-08-06
DK1224170T3 (da)	2009-12-07
EP1224170A1 (fr)	2002-07-24
HK1052505A1 (en)	2003-09-19
PL355433A1 (en)	2004-04-19
EP2157081A1 (fr)	2010-02-24
KR20070095996A (ko)	2007-10-01
CY1110067T1 (el)	2015-01-14
HU230416B1 (hu)	2016-05-30
DK1224170T5 (en)	2018-01-22

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Publication	Publication Date	Title
NO322746B1 (no)	2006-12-04	Indoliner, substituert i 6-stilling, og farmasoytisk preparat, samt anvendelse og fremstilling derav.
US6762180B1 (en)	2004-07-13	Substituted indolines which inhibit receptor tyrosine kinases
JP3952369B2 (ja)	2007-08-01	新規な置換インドリノン類、その製造及びその薬剤としての使用
EP1551830B1 (fr)	2009-04-08	Indolinones a subtitution heterocyclique, et leur utilisation en tant qu'inhibiteurs des recepteurs de tyrosine kinase
US20040058978A1 (en)	2004-03-25	Novel substituted indolines with an inhibitory effect on various kinases and complexes of CDKs
JP2005537276A (ja)	2005-12-08	６−置換インドリノン誘導体、その製法及び医薬組成物としての使用
US7514468B2 (en)	2009-04-07	Indolinone derivatives substituted in the 6 position, the preparation thereof and their use as pharmaceutical compositions
DE10042696A1 (de)	2002-03-14	In 6-Stellung substituierte Indolinone, ihre Herstellung und ihre Verwendung als Arzneimittel