EA013209B1 - Производные дифенилоксиндол-2-она и их применение для лечения рака - Google Patents

Info

Publication number

EA013209B1

EA013209B1 EA200601879A EA200601879A EA013209B1 EA 013209 B1 EA013209 B1 EA 013209B1 EA 200601879 A EA200601879 A EA 200601879A EA 200601879 A EA200601879 A EA 200601879A EA 013209 B1 EA013209 B1 EA 013209B1

Authority

EA

Eurasian Patent Office

Prior art keywords

bis

hydroxyphenyl

alkyl

optionally substituted

amino

Prior art date

2004-04-08

Links

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• Global Dossier
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• 206010028980 Neoplasm Diseases 0.000 title claims abstract description 45
• 201000011510 cancer Diseases 0.000 title claims abstract description 24
• NFGNXVVDIZKDGL-UHFFFAOYSA-N 3,4-diphenylindol-2-one Chemical class C12=C(C=3C=CC=CC=3)C(=O)N=C2C=CC=C1C1=CC=CC=C1 NFGNXVVDIZKDGL-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 140
• 239000003814 drug Substances 0.000 claims abstract description 20
• 241000124008 Mammalia Species 0.000 claims abstract description 10
• 238000002360 preparation method Methods 0.000 claims abstract description 7
• KLAWNELUVVBFGB-UHFFFAOYSA-N 3,3-diphenyl-1h-indol-2-one Chemical class O=C1NC2=CC=CC=C2C1(C=1C=CC=CC=1)C1=CC=CC=C1 KLAWNELUVVBFGB-UHFFFAOYSA-N 0.000 claims abstract description 5
• IHTKRPXYIKPMQJ-UHFFFAOYSA-N 6-chloro-3,3-bis(4-hydroxyphenyl)-7-methyl-1h-indol-2-one Chemical compound C12=CC=C(Cl)C(C)=C2NC(=O)C1(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 IHTKRPXYIKPMQJ-UHFFFAOYSA-N 0.000 claims abstract description 5
• -1 amino, carbamoyl Chemical group 0.000 claims description 129
• 150000002367 halogens Chemical class 0.000 claims description 111
• 229910052736 halogen Inorganic materials 0.000 claims description 91
• 125000001072 heteroaryl group Chemical group 0.000 claims description 78
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 67
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 62
• 239000001257 hydrogen Substances 0.000 claims description 60
• 229910052739 hydrogen Inorganic materials 0.000 claims description 60
• 125000003118 aryl group Chemical group 0.000 claims description 52
• 125000000217 alkyl group Chemical group 0.000 claims description 51
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 46
• 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 43
• 125000000623 heterocyclic group Chemical group 0.000 claims description 42
• 125000003545 alkoxy group Chemical group 0.000 claims description 41
• 150000002431 hydrogen Chemical class 0.000 claims description 35
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 31
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 31
• 125000001424 substituent group Chemical group 0.000 claims description 29
• 125000003107 substituted aryl group Chemical group 0.000 claims description 27
• 125000004104 aryloxy group Chemical group 0.000 claims description 26
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 25
• 125000004432 carbon atom Chemical group C* 0.000 claims description 25
• 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 24
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 23
• 150000003839 salts Chemical class 0.000 claims description 23
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 21
• 125000001769 aryl amino group Chemical group 0.000 claims description 20
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 19
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 18
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 17
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 16
• 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 16
• 125000004122 cyclic group Chemical group 0.000 claims description 16
• 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 15
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
• 125000003277 amino group Chemical group 0.000 claims description 15
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 14
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 14
• 239000008194 pharmaceutical composition Substances 0.000 claims description 14
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 13
• 125000005241 heteroarylamino group Chemical group 0.000 claims description 13
• 125000006598 aminocarbonylamino group Chemical group 0.000 claims description 12
• 125000005129 aryl carbonyl group Chemical group 0.000 claims description 12
• 125000002837 carbocyclic group Chemical group 0.000 claims description 11
• 229910052717 sulfur Inorganic materials 0.000 claims description 11
• 125000005842 heteroatom Chemical group 0.000 claims description 10
• 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 10
• 125000004043 oxo group Chemical group O=* 0.000 claims description 10
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
• 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 9
• 239000000460 chlorine Substances 0.000 claims description 9
• 229910052801 chlorine Inorganic materials 0.000 claims description 9
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 9
• 125000005419 heteroarylsulfonylamino group Chemical group 0.000 claims description 9
• 229910052760 oxygen Inorganic materials 0.000 claims description 9
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
• 125000004423 acyloxy group Chemical group 0.000 claims description 8
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 8
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
• 239000001301 oxygen Substances 0.000 claims description 8
• 239000011593 sulfur Substances 0.000 claims description 8
• 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 claims description 7
• 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 7
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
• 239000002246 antineoplastic agent Substances 0.000 claims description 6
• 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 6
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
• 229910052794 bromium Inorganic materials 0.000 claims description 6
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 6
• 229910052731 fluorine Inorganic materials 0.000 claims description 6
• 239000011737 fluorine Substances 0.000 claims description 6
• 229940127089 cytotoxic agent Drugs 0.000 claims description 5
• 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 5
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
• HFPFLPDWXYWYGL-UHFFFAOYSA-N 5-amino-6-chloro-3,3-bis(4-hydroxyphenyl)-7-methyl-1h-indol-2-one Chemical compound C12=CC(N)=C(Cl)C(C)=C2NC(=O)C1(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 HFPFLPDWXYWYGL-UHFFFAOYSA-N 0.000 claims description 4
• CAGNTOOUEJMVHF-UHFFFAOYSA-N 5-chloro-3,3-bis(4-hydroxyphenyl)-1h-indol-2-one Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC(Cl)=CC=C2NC1=O CAGNTOOUEJMVHF-UHFFFAOYSA-N 0.000 claims description 4
• CYBVXBHPYVXLRF-UHFFFAOYSA-N 6-chloro-3,3-bis(4-hydroxyphenyl)-7-methoxy-5-methyl-1h-indol-2-one Chemical compound C12=CC(C)=C(Cl)C(OC)=C2NC(=O)C1(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 CYBVXBHPYVXLRF-UHFFFAOYSA-N 0.000 claims description 4
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 4
• 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 4
• 125000001624 naphthyl group Chemical group 0.000 claims description 4
• 125000001725 pyrenyl group Chemical group 0.000 claims description 4
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
• QGSZBHGKGDFLRZ-UHFFFAOYSA-N 1-cyano-1-(diaminomethylideneamino)urea Chemical compound NC(N)=NN(C#N)C(N)=O QGSZBHGKGDFLRZ-UHFFFAOYSA-N 0.000 claims description 3
• MIRPQDACWRHIOL-UHFFFAOYSA-N 4,7-dichloro-3,3-bis(4-hydroxyphenyl)-1h-indol-2-one Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C(C(Cl)=CC=C2Cl)=C2NC1=O MIRPQDACWRHIOL-UHFFFAOYSA-N 0.000 claims description 3
• SALZXNNNVOTDIW-UHFFFAOYSA-N 5-[[3,3-bis(4-hydroxyphenyl)-7-methyl-2-oxo-1h-indol-6-yl]oxy]pentanoic acid Chemical compound C12=CC=C(OCCCCC(O)=O)C(C)=C2NC(=O)C1(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 SALZXNNNVOTDIW-UHFFFAOYSA-N 0.000 claims description 3
• ZDHWZITXXKHSPZ-UHFFFAOYSA-N 5-amino-3,3-bis(4-hydroxyphenyl)-1h-indol-2-one Chemical compound C12=CC(N)=CC=C2NC(=O)C1(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 ZDHWZITXXKHSPZ-UHFFFAOYSA-N 0.000 claims description 3
• MVJSBMCYQZTMQU-UHFFFAOYSA-N 5-amino-3,3-bis(4-hydroxyphenyl)-7-methyl-1h-indol-2-one Chemical compound CC1=CC(N)=CC2=C1NC(=O)C2(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 MVJSBMCYQZTMQU-UHFFFAOYSA-N 0.000 claims description 3
• XCRVUPAFQYGLKP-UHFFFAOYSA-N 5-chloro-3,3-bis(4-hydroxyphenyl)-7-methyl-1h-indol-2-one Chemical compound CC1=CC(Cl)=CC2=C1NC(=O)C2(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 XCRVUPAFQYGLKP-UHFFFAOYSA-N 0.000 claims description 3
• IJIHPPHCPHSQDI-UHFFFAOYSA-N 5-fluoro-3,3-bis(4-hydroxyphenyl)-1h-indol-2-one Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC(F)=CC=C2NC1=O IJIHPPHCPHSQDI-UHFFFAOYSA-N 0.000 claims description 3
• WNYAEOYJQAUSPV-UHFFFAOYSA-N 5-fluoro-3,3-bis(4-hydroxyphenyl)-7-methyl-1h-indol-2-one Chemical compound CC1=CC(F)=CC2=C1NC(=O)C2(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 WNYAEOYJQAUSPV-UHFFFAOYSA-N 0.000 claims description 3
• JNJKTURNCLNWAF-UHFFFAOYSA-N 6-bromo-3,3-bis(4-hydroxyphenyl)-7-methyl-1h-indol-2-one Chemical compound C12=CC=C(Br)C(C)=C2NC(=O)C1(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 JNJKTURNCLNWAF-UHFFFAOYSA-N 0.000 claims description 3
• DDEBKRYJUTXBLU-UHFFFAOYSA-N 6-chloro-3,3-bis(4-fluorophenyl)-7-methyl-1h-indol-2-one Chemical compound C12=CC=C(Cl)C(C)=C2NC(=O)C1(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 DDEBKRYJUTXBLU-UHFFFAOYSA-N 0.000 claims description 3
• DANZKDLAZRPRTG-UHFFFAOYSA-N 6-chloro-3,3-bis(4-hydroxyphenyl)-1,7-dimethylindol-2-one Chemical compound C12=CC=C(Cl)C(C)=C2N(C)C(=O)C1(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 DANZKDLAZRPRTG-UHFFFAOYSA-N 0.000 claims description 3
• HVMOAXFDEMGLCD-UHFFFAOYSA-N 6-chloro-7-fluoro-3,3-bis(4-hydroxyphenyl)-1h-indol-2-one Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C(C=CC(Cl)=C2F)=C2NC1=O HVMOAXFDEMGLCD-UHFFFAOYSA-N 0.000 claims description 3
• OVTWDLFNMYOKHF-UHFFFAOYSA-N 6-fluoro-3,3-bis(4-hydroxyphenyl)-1h-indol-2-one Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=C(F)C=C2NC1=O OVTWDLFNMYOKHF-UHFFFAOYSA-N 0.000 claims description 3
• UVKDUEWJVAMTDF-UHFFFAOYSA-N 6-fluoro-3,3-bis(4-hydroxyphenyl)-7-methyl-1h-indol-2-one Chemical compound C12=CC=C(F)C(C)=C2NC(=O)C1(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 UVKDUEWJVAMTDF-UHFFFAOYSA-N 0.000 claims description 3
• OFATZIAUDOCNFS-UHFFFAOYSA-N 7-bromo-3,3-bis(4-hydroxyphenyl)-1h-indol-2-one Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C(C=CC=C2Br)=C2NC1=O OFATZIAUDOCNFS-UHFFFAOYSA-N 0.000 claims description 3
• AGDSOGZAIXHTMD-UHFFFAOYSA-N 7-ethyl-3,3-bis(4-hydroxyphenyl)-1h-indol-2-one Chemical compound CCC1=CC=CC2=C1NC(=O)C2(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 AGDSOGZAIXHTMD-UHFFFAOYSA-N 0.000 claims description 3
• 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 3
• PAJLWXMEQQXQKM-UHFFFAOYSA-N methyl 5-[[3,3-bis(4-hydroxyphenyl)-7-methyl-2-oxo-1h-indol-6-yl]oxy]pentanoate Chemical compound CC=1C(OCCCCC(=O)OC)=CC=C2C=1NC(=O)C2(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 PAJLWXMEQQXQKM-UHFFFAOYSA-N 0.000 claims description 3
• ZKQSMLUZARHNFA-UHFFFAOYSA-N n-[4-[6-chloro-3-[4-(methanesulfonamido)phenyl]-7-methyl-2-oxo-1h-indol-3-yl]phenyl]methanesulfonamide Chemical compound C12=CC=C(Cl)C(C)=C2NC(=O)C1(C=1C=CC(NS(C)(=O)=O)=CC=1)C1=CC=C(NS(C)(=O)=O)C=C1 ZKQSMLUZARHNFA-UHFFFAOYSA-N 0.000 claims description 3
• 125000004434 sulfur atom Chemical group 0.000 claims description 3
• AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 claims description 2
• XQKBUNIECXVVHV-UHFFFAOYSA-N 3,3-bis(4-hydroxyphenyl)-2-oxo-1h-indole-5-carboxylic acid Chemical compound C12=CC(C(=O)O)=CC=C2NC(=O)C1(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 XQKBUNIECXVVHV-UHFFFAOYSA-N 0.000 claims description 2
• USEUWHHNJDYNIQ-UHFFFAOYSA-N 3,3-bis(4-hydroxyphenyl)-2-oxo-1h-indole-7-carbonitrile Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C(C=CC=C2C#N)=C2NC1=O USEUWHHNJDYNIQ-UHFFFAOYSA-N 0.000 claims description 2
• WEWQMABMPJELLQ-UHFFFAOYSA-N 3,3-bis(4-hydroxyphenyl)-4,7-dimethyl-1h-indol-2-one Chemical compound CC1=CC=C(C)C2=C1NC(=O)C2(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 WEWQMABMPJELLQ-UHFFFAOYSA-N 0.000 claims description 2
• VHDOKENBSOAEJT-UHFFFAOYSA-N 3,3-bis(4-hydroxyphenyl)-4-methoxy-1h-indol-2-one Chemical compound C1=2C(OC)=CC=CC=2NC(=O)C1(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 VHDOKENBSOAEJT-UHFFFAOYSA-N 0.000 claims description 2
• BBACGZRRRFJPAB-UHFFFAOYSA-N 3,3-bis(4-hydroxyphenyl)-5-(4-methylpiperazine-1-carbonyl)-1h-indol-2-one Chemical compound C1CN(C)CCN1C(=O)C1=CC=C(NC(=O)C2(C=3C=CC(O)=CC=3)C=3C=CC(O)=CC=3)C2=C1 BBACGZRRRFJPAB-UHFFFAOYSA-N 0.000 claims description 2
• TTXNKFPWVKWSOM-UHFFFAOYSA-N 3,3-bis(4-hydroxyphenyl)-5-(morpholine-4-carbonyl)-1h-indol-2-one Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC(C(=O)N3CCOCC3)=CC=C2NC1=O TTXNKFPWVKWSOM-UHFFFAOYSA-N 0.000 claims description 2
• RNURUGHYXGJHIO-UHFFFAOYSA-N 3,3-bis(4-hydroxyphenyl)-5-iodo-1h-indol-2-one Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC(I)=CC=C2NC1=O RNURUGHYXGJHIO-UHFFFAOYSA-N 0.000 claims description 2
• YJOCGHWNWZBQSJ-UHFFFAOYSA-N 3,3-bis(4-hydroxyphenyl)-5-methoxy-7-methyl-1h-indol-2-one Chemical compound CC1=CC(OC)=CC2=C1NC(=O)C2(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 YJOCGHWNWZBQSJ-UHFFFAOYSA-N 0.000 claims description 2
• XXUDCZSQKNLZAX-UHFFFAOYSA-N 3,3-bis(4-hydroxyphenyl)-5-nitro-1h-indol-2-one Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC([N+]([O-])=O)=CC=C2NC1=O XXUDCZSQKNLZAX-UHFFFAOYSA-N 0.000 claims description 2
• BXSGSHWSLSFKDJ-UHFFFAOYSA-N 3,3-bis(4-hydroxyphenyl)-5-phenyl-1h-indol-2-one Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC(C=3C=CC=CC=3)=CC=C2NC1=O BXSGSHWSLSFKDJ-UHFFFAOYSA-N 0.000 claims description 2
• VEOCUPMQNPJMEC-UHFFFAOYSA-N 3,3-bis(4-hydroxyphenyl)-5-pyridin-4-yl-1h-indol-2-one Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC(C=3C=CN=CC=3)=CC=C2NC1=O VEOCUPMQNPJMEC-UHFFFAOYSA-N 0.000 claims description 2
• LVNIVKYTMYSDGR-UHFFFAOYSA-N 3,3-bis(4-hydroxyphenyl)-5-thiophen-2-yl-1h-indol-2-one Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC(C=3SC=CC=3)=CC=C2NC1=O LVNIVKYTMYSDGR-UHFFFAOYSA-N 0.000 claims description 2
• HOJZIXIIRFLACX-UHFFFAOYSA-N 3,3-bis(4-hydroxyphenyl)-6-methoxy-1h-indol-2-one Chemical compound C=1C(OC)=CC=C2C=1NC(=O)C2(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 HOJZIXIIRFLACX-UHFFFAOYSA-N 0.000 claims description 2
• GZADXGQIIJFSBT-UHFFFAOYSA-N 3,3-bis(4-hydroxyphenyl)-6-methoxy-7-methyl-1h-indol-2-one Chemical compound CC=1C(OC)=CC=C2C=1NC(=O)C2(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 GZADXGQIIJFSBT-UHFFFAOYSA-N 0.000 claims description 2
• YGNOZFWOSFFWIB-UHFFFAOYSA-N 3,3-bis(4-hydroxyphenyl)-7-(3-methoxyprop-1-ynyl)-1h-indol-2-one Chemical compound COCC#CC1=CC=CC2=C1NC(=O)C2(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 YGNOZFWOSFFWIB-UHFFFAOYSA-N 0.000 claims description 2
• PUPXQVHSOIGTAO-UHFFFAOYSA-N 3,3-bis(4-hydroxyphenyl)-7-(4-methylpiperazine-1-carbonyl)-1h-indol-2-one Chemical compound C1CN(C)CCN1C(=O)C1=CC=CC2=C1NC(=O)C2(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 PUPXQVHSOIGTAO-UHFFFAOYSA-N 0.000 claims description 2
• NVFBSUYGWKQZFP-UHFFFAOYSA-N 3,3-bis(4-hydroxyphenyl)-7-(morpholine-4-carbonyl)-1h-indol-2-one Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C(C=CC=C2C(=O)N3CCOCC3)=C2NC1=O NVFBSUYGWKQZFP-UHFFFAOYSA-N 0.000 claims description 2
• DOGXFLMCFMBBGH-UHFFFAOYSA-N 3,3-bis(4-hydroxyphenyl)-7-(trifluoromethyl)-1h-indol-2-one Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C(C=CC=C2C(F)(F)F)=C2NC1=O DOGXFLMCFMBBGH-UHFFFAOYSA-N 0.000 claims description 2
• VNJYEDZLQRQMLV-UHFFFAOYSA-N 3,3-bis(4-hydroxyphenyl)-7-iodo-1h-indol-2-one Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C(C=CC=C2I)=C2NC1=O VNJYEDZLQRQMLV-UHFFFAOYSA-N 0.000 claims description 2
• USVYGRFFGUJULC-UHFFFAOYSA-N 3,3-bis(4-hydroxyphenyl)-7-methoxy-1h-indol-2-one Chemical compound COC1=CC=CC2=C1NC(=O)C2(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 USVYGRFFGUJULC-UHFFFAOYSA-N 0.000 claims description 2
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