JP3952369B2 - 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 - Google Patents

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Publication number

JP3952369B2

JP3952369B2 JP2001519696A JP2001519696A JP3952369B2 JP 3952369 B2 JP3952369 B2 JP 3952369B2 JP 2001519696 A JP2001519696 A JP 2001519696A JP 2001519696 A JP2001519696 A JP 2001519696A JP 3952369 B2 JP3952369 B2 JP 3952369B2

Authority

JP

Japan

Prior art keywords

group

alkyl

phenyl

indolinone

amino

Prior art date

1999-08-27

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

Expired - Fee Related

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• JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical class C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 title claims description 12
• 238000004519 manufacturing process Methods 0.000 title claims 4
• 239000003814 drug Substances 0.000 title description 2
• -1 aryl-C 1-3 -alkyl Chemical group 0.000 claims description 209
• 150000001875 compounds Chemical class 0.000 claims description 78
• 125000000217 alkyl group Chemical group 0.000 claims description 50
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 49
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 38
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 27
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 26
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
• 150000003839 salts Chemical class 0.000 claims description 24
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 21
• 229910052739 hydrogen Inorganic materials 0.000 claims description 20
• 239000001257 hydrogen Substances 0.000 claims description 20
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 17
• 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 16
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
• 125000006842 cycloalkyleneimino group Chemical group 0.000 claims description 16
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 16
• 125000003282 alkyl amino group Chemical group 0.000 claims description 15
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 15
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
• 125000006576 di-(C1-C3-alkyl)-aminocarbonyl group Chemical group 0.000 claims description 14
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
• 229910052757 nitrogen Inorganic materials 0.000 claims description 14
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 14
• 125000006563 (C1-3) alkylaminocarbonyl group Chemical group 0.000 claims description 13
• 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims description 13
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 13
• 229910052760 oxygen Inorganic materials 0.000 claims description 13
• 239000001301 oxygen Substances 0.000 claims description 13
• 229910052717 sulfur Inorganic materials 0.000 claims description 13
• 125000004434 sulfur atom Chemical group 0.000 claims description 13
• 229910052801 chlorine Inorganic materials 0.000 claims description 12
• 239000000460 chlorine Substances 0.000 claims description 12
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
• 125000001841 imino group Chemical group [H]N=* 0.000 claims description 12
• 229910052740 iodine Inorganic materials 0.000 claims description 12
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
• DZXGPNIPADQITJ-UHFFFAOYSA-N 6-amino-3-[C-phenyl-N-[4-(piperidin-1-ylmethyl)phenyl]carbonimidoyl]-1H-indol-2-ol Chemical compound C1CCN(CC1)CC2=CC=C(C=C2)N=C(C3=CC=CC=C3)C4=C(NC5=C4C=CC(=C5)N)O DZXGPNIPADQITJ-UHFFFAOYSA-N 0.000 claims description 11
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 11
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
• 229910052794 bromium Inorganic materials 0.000 claims description 11
• 229910052731 fluorine Inorganic materials 0.000 claims description 11
• 239000011737 fluorine Substances 0.000 claims description 11
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 10
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 10
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
• 125000006597 (C1-C3) alkylcarbonylamino group Chemical group 0.000 claims description 8
• 125000003545 alkoxy group Chemical group 0.000 claims description 8
• 125000003277 amino group Chemical group 0.000 claims description 8
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 8
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 7
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 7
• 230000004663 cell proliferation Effects 0.000 claims description 7
• 125000001072 heteroaryl group Chemical group 0.000 claims description 7
• 238000000034 method Methods 0.000 claims description 7
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 7
• 125000006594 (C1-C3) alkylsulfony group Chemical group 0.000 claims description 6
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 6
• 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims description 6
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
• 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 6
• 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims description 5
• AZVWGKHOXIGUOR-RQZHXJHFSA-N n-[4-[[(z)-(5,6-dimethoxy-2-oxo-1h-indol-3-ylidene)-phenylmethyl]amino]phenyl]-2-(dimethylamino)-n-methylacetamide Chemical compound C1=2C=C(OC)C(OC)=CC=2NC(=O)\C1=C(C=1C=CC=CC=1)/NC1=CC=C(N(C)C(=O)CN(C)C)C=C1 AZVWGKHOXIGUOR-RQZHXJHFSA-N 0.000 claims description 5
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 5
• 125000006603 (C1-C3) alkylaminosulfonyl group Chemical group 0.000 claims description 4
• 125000002252 acyl group Chemical group 0.000 claims description 4
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
• 125000003118 aryl group Chemical group 0.000 claims description 4
• 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 4
• 238000001727 in vivo Methods 0.000 claims description 4
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
• 239000008194 pharmaceutical composition Substances 0.000 claims description 4
• 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 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
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
• 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 4
• 125000003396 thiol group Chemical class [H]S* 0.000 claims description 4
• DZDLXZDQXFWNIZ-KTMFPKCZSA-N (3z)-3-[[4-[[benzyl(methyl)amino]methyl]anilino]-phenylmethylidene]-5,6-dimethoxy-1h-indol-2-one Chemical compound C1=2C=C(OC)C(OC)=CC=2NC(=O)\C1=C(C=1C=CC=CC=1)/NC(C=C1)=CC=C1CN(C)CC1=CC=CC=C1 DZDLXZDQXFWNIZ-KTMFPKCZSA-N 0.000 claims description 3
• YQCDPGUCLMSKKA-DQSJHHFOSA-N (3z)-5,6-dimethoxy-3-[phenyl-[4-(piperidin-1-ylmethyl)anilino]methylidene]-1h-indol-2-one Chemical compound C1=2C=C(OC)C(OC)=CC=2NC(=O)\C1=C(C=1C=CC=CC=1)/NC(C=C1)=CC=C1CN1CCCCC1 YQCDPGUCLMSKKA-DQSJHHFOSA-N 0.000 claims description 3
• 125000006595 (C1-C3) alkylsulfinyl group Chemical group 0.000 claims description 3
• VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 3
• 125000004414 alkyl thio group Chemical group 0.000 claims description 3
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
• 239000000969 carrier Substances 0.000 claims description 3
• 239000003085 diluting agent Substances 0.000 claims description 3
• 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
• UCNFEIGFIXSULX-DQSJHHFOSA-N n-[4-[[(z)-(5,6-dimethoxy-2-oxo-1h-indol-3-ylidene)-phenylmethyl]amino]phenyl]-n-[2-(dimethylamino)ethyl]acetamide Chemical compound C1=2C=C(OC)C(OC)=CC=2NC(=O)\C1=C(C=1C=CC=CC=1)/NC1=CC=C(N(CCN(C)C)C(C)=O)C=C1 UCNFEIGFIXSULX-DQSJHHFOSA-N 0.000 claims description 3
• LMEVITQHJRHCLI-ZIADKAODSA-N n-[4-[[(z)-(5,6-dimethoxy-2-oxo-1h-indol-3-ylidene)-phenylmethyl]amino]phenyl]-n-[3-(dimethylamino)propyl]acetamide Chemical compound C1=2C=C(OC)C(OC)=CC=2NC(=O)\C1=C(C=1C=CC=CC=1)/NC1=CC=C(N(CCCN(C)C)C(C)=O)C=C1 LMEVITQHJRHCLI-ZIADKAODSA-N 0.000 claims description 3
• 125000004076 pyridyl group Chemical group 0.000 claims description 3
• 239000000126 substance Substances 0.000 claims description 3
• 125000006602 (C1-C3) alkylsulfonylamino group Chemical group 0.000 claims description 2
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
• 125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
• 125000004104 aryloxy group Chemical group 0.000 claims description 2
• 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 2
• 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 2
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 2
• 125000001153 fluoro group Chemical group F* 0.000 claims description 2
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 2
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
• 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 2
• 125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 claims description 2
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
• 125000003944 tolyl group Chemical group 0.000 claims description 2
• 125000002883 imidazolyl group Chemical group 0.000 claims 2
• 230000002159 abnormal effect Effects 0.000 claims 1
• CREXVNNSNOKDHW-UHFFFAOYSA-N azaniumylideneazanide Chemical group N[N] CREXVNNSNOKDHW-UHFFFAOYSA-N 0.000 claims 1
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
• 210000002784 stomach Anatomy 0.000 claims 1
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 357
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 342
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 134
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 120
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 119
• 239000000741 silica gel Substances 0.000 description 118
• 229910002027 silica gel Inorganic materials 0.000 description 118
• 239000007858 starting material Substances 0.000 description 101
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 90
• 238000000119 electrospray ionisation mass spectrum Methods 0.000 description 69
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 66
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 58
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 58
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 48
• WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 44
• 239000000203 mixture Substances 0.000 description 44
• 238000001819 mass spectrum Methods 0.000 description 37
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
• 239000002904 solvent Substances 0.000 description 33
• LTDNARBYDJUQRZ-UHFFFAOYSA-N 1-acetyl-3-[ethoxy(phenyl)methylidene]-5,6-dimethoxyindol-2-one Chemical compound O=C1N(C(C)=O)C2=CC(OC)=C(OC)C=C2C1=C(OCC)C1=CC=CC=C1 LTDNARBYDJUQRZ-UHFFFAOYSA-N 0.000 description 27
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 24
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 23
• 239000000243 solution Substances 0.000 description 23
• 229960000583 acetic acid Drugs 0.000 description 22
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 20
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
• QBFIMWPRXFDRPY-UHFFFAOYSA-N 1-acetyl-3-(1-ethoxypropylidene)-5,6-dimethoxyindol-2-one Chemical compound COC1=C(OC)C=C2C(=C(CC)OCC)C(=O)N(C(C)=O)C2=C1 QBFIMWPRXFDRPY-UHFFFAOYSA-N 0.000 description 17
• 238000001704 evaporation Methods 0.000 description 17
• 230000008020 evaporation Effects 0.000 description 17
• 239000012362 glacial acetic acid Substances 0.000 description 16
• 239000002253 acid Substances 0.000 description 15
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
• 239000002244 precipitate Substances 0.000 description 14
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 13
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 13
• 239000013543 active substance Substances 0.000 description 13
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
• 210000004027 cell Anatomy 0.000 description 11
• 238000006243 chemical reaction Methods 0.000 description 11
• 230000002829 reductive effect Effects 0.000 description 11
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
• 229910021529 ammonia Inorganic materials 0.000 description 10
• 239000003054 catalyst Substances 0.000 description 10
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
• 125000006239 protecting group Chemical group 0.000 description 10
• 229910052938 sodium sulfate Inorganic materials 0.000 description 10
• 235000011152 sodium sulphate Nutrition 0.000 description 10
• DRYFDUUAYSVNSN-UHFFFAOYSA-N 4-(piperidin-1-ylmethyl)aniline Chemical compound C1=CC(N)=CC=C1CN1CCCCC1 DRYFDUUAYSVNSN-UHFFFAOYSA-N 0.000 description 9
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 9
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 9
• 230000002401 inhibitory effect Effects 0.000 description 9
• 239000000047 product Substances 0.000 description 9
• FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
• 238000003756 stirring Methods 0.000 description 9
• JGSJGUYWZLIULD-DQRAZIAOSA-N (3z)-3-[anilino(phenyl)methylidene]-5,6-dimethoxy-1h-indol-2-one Chemical compound C1=2C=C(OC)C(OC)=CC=2NC(=O)\C1=C(C=1C=CC=CC=1)/NC1=CC=CC=C1 JGSJGUYWZLIULD-DQRAZIAOSA-N 0.000 description 8
• 239000002585 base Substances 0.000 description 8
• XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical compound OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 8
• 210000002889 endothelial cell Anatomy 0.000 description 8
• 239000000706 filtrate Substances 0.000 description 8
• 239000003208 petroleum Substances 0.000 description 8
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 7
• 238000001816 cooling Methods 0.000 description 7
• 150000007530 organic bases Chemical group 0.000 description 7
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
• GYARBZXYJMKSCI-DQRAZIAOSA-N (3z)-5,6-dimethoxy-3-[(4-nitroanilino)-phenylmethylidene]-1h-indol-2-one Chemical compound C1=2C=C(OC)C(OC)=CC=2NC(=O)\C1=C(C=1C=CC=CC=1)/NC1=CC=C([N+]([O-])=O)C=C1 GYARBZXYJMKSCI-DQRAZIAOSA-N 0.000 description 6
• BFTKTMUEKYRZRR-UHFFFAOYSA-N 1-acetyl-3-[ethoxy(phenyl)methylidene]-6-phenylindol-2-one Chemical compound C=1C=CC=CC=1C(OCC)=C(C1=CC=2)C(=O)N(C(C)=O)C1=CC=2C1=CC=CC=C1 BFTKTMUEKYRZRR-UHFFFAOYSA-N 0.000 description 6
• HEPMOEJAPUVTEF-FCQUAONHSA-N 4-[[(z)-(5,6-dimethoxy-2-oxo-1h-indol-3-ylidene)-phenylmethyl]amino]benzonitrile Chemical compound C1=2C=C(OC)C(OC)=CC=2NC(=O)\C1=C(C=1C=CC=CC=1)/NC1=CC=C(C#N)C=C1 HEPMOEJAPUVTEF-FCQUAONHSA-N 0.000 description 6
• JARRYVQFBQVOBE-UHFFFAOYSA-N 6-bromo-1,3-dihydroindol-2-one Chemical compound BrC1=CC=C2CC(=O)NC2=C1 JARRYVQFBQVOBE-UHFFFAOYSA-N 0.000 description 6
• BPHPZKCNQDGMHU-UHFFFAOYSA-N 7-[methoxy(phenyl)methylidene]-5h-[1,3]dioxolo[4,5-f]indol-6-one Chemical compound O=C1NC2=CC=3OCOC=3C=C2C1=C(OC)C1=CC=CC=C1 BPHPZKCNQDGMHU-UHFFFAOYSA-N 0.000 description 6
• QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 6
• BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 description 6
• 238000009835 boiling Methods 0.000 description 6
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