JP2015514762A5 - - Google Patents
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- Publication number
- JP2015514762A5 JP2015514762A5 JP2015507031A JP2015507031A JP2015514762A5 JP 2015514762 A5 JP2015514762 A5 JP 2015514762A5 JP 2015507031 A JP2015507031 A JP 2015507031A JP 2015507031 A JP2015507031 A JP 2015507031A JP 2015514762 A5 JP2015514762 A5 JP 2015514762A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrrol
- oxoindoline
- dimethyl
- ureido
- amide
- Prior art date
- 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.)
- Granted
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- -1 nitrobenzoyl Chemical group 0.000 claims description 234
- 125000003118 aryl group Chemical group 0.000 claims description 79
- 229910052739 hydrogen Inorganic materials 0.000 claims description 51
- 239000001257 hydrogen Substances 0.000 claims description 50
- 125000001072 heteroaryl group Chemical group 0.000 claims description 31
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 30
- 125000005224 heteroarylcarbonylamino group Chemical group 0.000 claims description 29
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 28
- 150000002431 hydrogen Chemical class 0.000 claims description 27
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 25
- ZXNZHVDQMZJUKH-UHFFFAOYSA-N 1-(4-fluorophenyl)-2-oxopyridine-3-carboxamide Chemical compound O=C1C(C(=O)N)=CC=CN1C1=CC=C(F)C=C1 ZXNZHVDQMZJUKH-UHFFFAOYSA-N 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 24
- 125000005843 halogen group Chemical group 0.000 claims description 24
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 19
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 16
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 11
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 10
- 125000005429 oxyalkyl group Chemical group 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 8
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- JLLMYQUWKPBJIP-UHFFFAOYSA-N C1=CC(=CC=C1C2=CN=CC(C2=O)C(=O)N)F Chemical compound C1=CC(=CC=C1C2=CN=CC(C2=O)C(=O)N)F JLLMYQUWKPBJIP-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
- BYNJVONMVRJJFE-UHFFFAOYSA-N 1-(2-fluorophenyl)-2-oxopyridine-3-carboxamide Chemical compound O=C1C(C(=O)N)=CC=CN1C1=CC=CC=C1F BYNJVONMVRJJFE-UHFFFAOYSA-N 0.000 claims description 6
- OIODHEBQYUBPFJ-UHFFFAOYSA-N 1-(2-hydroxyethyl)-2-oxopyridine-3-carboxamide Chemical compound NC(=O)C1=CC=CN(CCO)C1=O OIODHEBQYUBPFJ-UHFFFAOYSA-N 0.000 claims description 6
- VXUZIEIANGFZOA-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-2-oxopyridine-3-carboxamide Chemical compound O=C1C(C(=O)N)=CC=CN1C1=CC=C(Cl)C(Cl)=C1 VXUZIEIANGFZOA-UHFFFAOYSA-N 0.000 claims description 6
- BWOPXYDWYZDIEL-UHFFFAOYSA-N 1-(3-chlorophenyl)-2-oxopyridine-3-carboxamide Chemical compound O=C1C(C(=O)N)=CC=CN1C1=CC=CC(Cl)=C1 BWOPXYDWYZDIEL-UHFFFAOYSA-N 0.000 claims description 6
- DXNNTFYSWVVFFC-UHFFFAOYSA-N 1-(4-methoxyphenyl)-2-oxopyridine-3-carboxamide Chemical compound C1=CC(OC)=CC=C1N1C(=O)C(C(N)=O)=CC=C1 DXNNTFYSWVVFFC-UHFFFAOYSA-N 0.000 claims description 6
- BGFDDFWHLWWLPC-UHFFFAOYSA-N 1-(4-methylphenyl)-2-oxopyridine-3-carboxamide Chemical compound C1=CC(C)=CC=C1N1C(=O)C(C(N)=O)=CC=C1 BGFDDFWHLWWLPC-UHFFFAOYSA-N 0.000 claims description 6
- QFXAYLJEIJWKJR-UHFFFAOYSA-N 2-oxo-1-phenylpyridine-3-carboxamide Chemical compound O=C1C(C(=O)N)=CC=CN1C1=CC=CC=C1 QFXAYLJEIJWKJR-UHFFFAOYSA-N 0.000 claims description 6
- QKKYGAZCGQVPNY-UHFFFAOYSA-N 4-oxo-5-phenyl-3H-pyridine-3-carboxamide Chemical compound C1(=CC=CC=C1)C=1C(C(C=NC1)C(=O)N)=O QKKYGAZCGQVPNY-UHFFFAOYSA-N 0.000 claims description 6
- OMQXRQQINGQXAF-UHFFFAOYSA-N 5-(3,5-difluorophenyl)-4-oxo-3H-pyridine-3-carboxamide Chemical compound FC=1C=C(C=C(C1)F)C=1C(C(C=NC1)C(=O)N)=O OMQXRQQINGQXAF-UHFFFAOYSA-N 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- LYWWJBMTDVEBEA-UHFFFAOYSA-N COC1=CC=C(C=C1)C=1C(C(C=NC1)C(=O)N)=O Chemical compound COC1=CC=C(C=C1)C=1C(C(C=NC1)C(=O)N)=O LYWWJBMTDVEBEA-UHFFFAOYSA-N 0.000 claims description 6
- LATLJHJRXCVGCK-UHFFFAOYSA-N ClC1=CC=C(C=C1)C=1C(C(C=NC1)C(=O)N)=O Chemical compound ClC1=CC=C(C=C1)C=1C(C(C=NC1)C(=O)N)=O LATLJHJRXCVGCK-UHFFFAOYSA-N 0.000 claims description 6
- MKJQDUVSMFSNIC-UHFFFAOYSA-N ClC=1C=C(C=CC=1)C=1C(C(C=NC=1)C(=O)N)=O Chemical compound ClC=1C=C(C=CC=1)C=1C(C(C=NC=1)C(=O)N)=O MKJQDUVSMFSNIC-UHFFFAOYSA-N 0.000 claims description 6
- 125000005605 benzo group Chemical group 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- DGALDZCQHLLQLF-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-oxopyridine-3-carboxamide Chemical compound O=C1C(C(=O)N)=CC=CN1C1=CC=C(Cl)C=C1 DGALDZCQHLLQLF-UHFFFAOYSA-N 0.000 claims description 4
- YKUZYUUESIPGMR-UHFFFAOYSA-N 1-methyl-2-oxopyridine-3-carboxamide Chemical compound CN1C=CC=C(C(N)=O)C1=O YKUZYUUESIPGMR-UHFFFAOYSA-N 0.000 claims description 4
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- OACPRYMPBJXXEB-UHFFFAOYSA-N 2-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound O=C1C(C(=O)N)=CC=CN1C1=CC=CC(C(F)(F)F)=C1 OACPRYMPBJXXEB-UHFFFAOYSA-N 0.000 claims description 4
- WEOWOKPUWZUTCX-UHFFFAOYSA-N 2-oxo-1-[4-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound O=C1C(C(=O)N)=CC=CN1C1=CC=C(C(F)(F)F)C=C1 WEOWOKPUWZUTCX-UHFFFAOYSA-N 0.000 claims description 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000001999 4-Methoxybenzoyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C(*)=O 0.000 claims description 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- DWCAXBZZSIJMLJ-UHFFFAOYSA-N 5-(2-fluorophenyl)-4-oxo-3H-pyridine-3-carboxamide Chemical compound FC1=C(C=CC=C1)C=1C(C(C=NC1)C(=O)N)=O DWCAXBZZSIJMLJ-UHFFFAOYSA-N 0.000 claims description 4
- IZONJUZIAYLCNY-UHFFFAOYSA-N 5-(4-fluorophenyl)-1-methyl-4-oxopyridine-3-carboxamide Chemical compound CN1C=C(C(N)=O)C(=O)C(C=2C=CC(F)=CC=2)=C1 IZONJUZIAYLCNY-UHFFFAOYSA-N 0.000 claims description 4
- STGQLOKVLLKATH-UHFFFAOYSA-N 5-methyl-4-oxo-3H-pyridine-3-carboxamide Chemical compound CC=1C(C(C=NC1)C(=O)N)=O STGQLOKVLLKATH-UHFFFAOYSA-N 0.000 claims description 4
- YXRKGWLSNMIRPJ-UHFFFAOYSA-N C1=CC(=C(C=C1F)F)C2=CN=CC(C2=O)C(=O)N Chemical compound C1=CC(=C(C=C1F)F)C2=CN=CC(C2=O)C(=O)N YXRKGWLSNMIRPJ-UHFFFAOYSA-N 0.000 claims description 4
- FKQMOACCOFCEPC-UHFFFAOYSA-N C1=CC(=CC=C1C2=CN=CC(C2=O)C(=O)N)C(F)(F)F Chemical compound C1=CC(=CC=C1C2=CN=CC(C2=O)C(=O)N)C(F)(F)F FKQMOACCOFCEPC-UHFFFAOYSA-N 0.000 claims description 4
- GOCCHNNSPOIAIQ-UHFFFAOYSA-N CC1=CC=C(C=C1)C2=CN=CC(C2=O)C(=O)N Chemical compound CC1=CC=C(C=C1)C2=CN=CC(C2=O)C(=O)N GOCCHNNSPOIAIQ-UHFFFAOYSA-N 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- 206010028980 Neoplasm Diseases 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 4
- 125000005116 aryl carbamoyl group Chemical group 0.000 claims description 4
- 201000011510 cancer Diseases 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- KIYYVAZSKZMMHH-UHFFFAOYSA-N 1-[4-chloro-3-(trifluoromethyl)phenyl]-2-oxopyridine-3-carboxamide Chemical compound O=C1C(C(=O)N)=CC=CN1C1=CC=C(Cl)C(C(F)(F)F)=C1 KIYYVAZSKZMMHH-UHFFFAOYSA-N 0.000 claims description 3
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- AIMMVWOEOZMVMS-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1 AIMMVWOEOZMVMS-UHFFFAOYSA-N 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- VWRNVLIFYHFPKL-UHFFFAOYSA-N 1-(4-chlorophenyl)-5-[[3-[4-chloro-3-(trifluoromethyl)phenyl]-2-oxoimidazolidine-1-carbonyl]amino]-2-oxo-4-[[2-oxo-3-[4-(trifluoromethyl)phenyl]imidazolidine-1-carbonyl]amino]pyridine-3-carboxamide Chemical compound FC(C=1C=C(C=CC1Cl)N1C(N(CC1)C(=O)NC=1C(=C(C(N(C1)C1=CC=C(C=C1)Cl)=O)C(=O)N)NC(=O)N1C(N(CC1)C1=CC=C(C=C1)C(F)(F)F)=O)=O)(F)F VWRNVLIFYHFPKL-UHFFFAOYSA-N 0.000 claims description 2
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 2
- PQEODESDYZMGKS-UHFFFAOYSA-N 2-oxo-4-[[2-oxo-1-[4-(trifluoromethyl)phenyl]pyridine-3-carbonyl]amino]-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound FC(C1=CC=C(C=C1)N1C(C(=CC=C1)C(=O)NC1=C(C(N(C=C1)C1=CC(=CC=C1)C(F)(F)F)=O)C(=O)N)=O)(F)F PQEODESDYZMGKS-UHFFFAOYSA-N 0.000 claims description 2
- AWDGJIPHYQTAKI-UHFFFAOYSA-N 3-[4-chloro-3-(trifluoromethyl)phenyl]-2-oxo-N-[2-oxo-3-[4-(trifluoromethyl)phenyl]imidazolidin-1-yl]imidazolidine-1-carboxamide Chemical compound FC(C=1C=C(C=CC1Cl)N1C(N(CC1)C(=O)NN1C(N(CC1)C1=CC=C(C=C1)C(F)(F)F)=O)=O)(F)F AWDGJIPHYQTAKI-UHFFFAOYSA-N 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- BOBDNCHHPMUADG-UNOMPAQXSA-N (3Z)-6-[2-oxo-3-[4-(trifluoromethyl)phenyl]imidazolidin-1-yl]-3-(1H-pyrrol-2-ylmethylidene)-1H-indol-2-one Chemical compound N1C(=CC=C1)\C=C\1/C(NC2=CC(=CC=C12)N1C(N(CC1)C1=CC=C(C=C1)C(F)(F)F)=O)=O BOBDNCHHPMUADG-UNOMPAQXSA-N 0.000 claims 1
- YLPDDWDFRUSKEB-UYRXBGFRSA-N 1-(2-fluorophenyl)-2-oxo-n-[(3z)-2-oxo-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-6-yl]pyridine-3-carboxamide Chemical compound FC1=CC=CC=C1N1C(=O)C(C(=O)NC=2C=C3NC(=O)C(=C\C=4NC=CC=4)/C3=CC=2)=CC=C1 YLPDDWDFRUSKEB-UYRXBGFRSA-N 0.000 claims 1
- LFTYGPMTDFTUPQ-BOPFTXTBSA-N 1-(2-hydroxyethyl)-2-oxo-n-[(3z)-2-oxo-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-6-yl]pyridine-3-carboxamide Chemical compound O=C1N(CCO)C=CC=C1C(=O)NC1=CC=C(\C(=C\C=2NC=CC=2)C(=O)N2)C2=C1 LFTYGPMTDFTUPQ-BOPFTXTBSA-N 0.000 claims 1
- HNQTUYPORHOBCX-ODLFYWEKSA-N 1-(3,4-dichlorophenyl)-2-oxo-n-[(3z)-2-oxo-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-6-yl]pyridine-3-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1N1C(=O)C(C(=O)NC=2C=C3NC(=O)C(=C\C=4NC=CC=4)/C3=CC=2)=CC=C1 HNQTUYPORHOBCX-ODLFYWEKSA-N 0.000 claims 1
- GZTMXOFGZLNTJS-BKUYFWCQSA-N 1-(3-chlorophenyl)-2-oxo-n-[(3z)-2-oxo-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-6-yl]pyridine-3-carboxamide Chemical compound ClC1=CC=CC(N2C(C(C(=O)NC=3C=C4NC(=O)C(=C\C=5NC=CC=5)/C4=CC=3)=CC=C2)=O)=C1 GZTMXOFGZLNTJS-BKUYFWCQSA-N 0.000 claims 1
- UDMYEAZQRQCCMJ-BKUYFWCQSA-N 1-(4-chlorophenyl)-2-oxo-n-[(3z)-2-oxo-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-6-yl]pyridine-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C(C(=O)NC=2C=C3NC(=O)C(=C\C=4NC=CC=4)/C3=CC=2)=CC=C1 UDMYEAZQRQCCMJ-BKUYFWCQSA-N 0.000 claims 1
- XDRNSONQGZAXAG-RGEXLXHISA-N 1-(4-fluorophenyl)-2-oxo-n-[(3z)-2-oxo-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-4-yl]pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C(=O)NC=2C=3C(=C/C=4NC=CC=4)/C(=O)NC=3C=CC=2)=CC=C1 XDRNSONQGZAXAG-RGEXLXHISA-N 0.000 claims 1
- JJXDTKCNLYIONS-BKUYFWCQSA-N 1-(4-fluorophenyl)-2-oxo-n-[(3z)-2-oxo-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-5-yl]pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C(=O)NC=2C=C3C(=C/C=4NC=CC=4)/C(=O)NC3=CC=2)=CC=C1 JJXDTKCNLYIONS-BKUYFWCQSA-N 0.000 claims 1
- JHVBIUJTSAGFKH-BKUYFWCQSA-N 1-(4-fluorophenyl)-2-oxo-n-[(3z)-2-oxo-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-6-yl]pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C(=O)NC=2C=C3NC(=O)C(=C\C=4NC=CC=4)/C3=CC=2)=CC=C1 JHVBIUJTSAGFKH-BKUYFWCQSA-N 0.000 claims 1
- CJGSUQOGGYGANV-ZHZULCJRSA-N 1-(4-fluorophenyl)-2-oxo-n-[(3z)-2-oxo-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-7-yl]pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)C(C(=O)NC=2C=3NC(=O)C(=C\C=4NC=CC=4)/C=3C=CC=2)=CC=C1 CJGSUQOGGYGANV-ZHZULCJRSA-N 0.000 claims 1
- LLXJJBGOKYODAN-HMAPJEAMSA-N 1-(4-methoxyphenyl)-2-oxo-n-[(3z)-2-oxo-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-6-yl]pyridine-3-carboxamide Chemical compound C1=CC(OC)=CC=C1N1C(=O)C(C(=O)NC=2C=C3NC(=O)C(=C\C=4NC=CC=4)/C3=CC=2)=CC=C1 LLXJJBGOKYODAN-HMAPJEAMSA-N 0.000 claims 1
- GGWSDEWIQKTJQS-HMAPJEAMSA-N 1-(4-methylphenyl)-2-oxo-n-[(3z)-2-oxo-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-6-yl]pyridine-3-carboxamide Chemical compound C1=CC(C)=CC=C1N1C(=O)C(C(=O)NC=2C=C3NC(=O)C(=C\C=4NC=CC=4)/C3=CC=2)=CC=C1 GGWSDEWIQKTJQS-HMAPJEAMSA-N 0.000 claims 1
- GDYQNHDEYPXVIM-YBEGLDIGSA-N 1-methyl-2-oxo-n-[(3z)-2-oxo-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-6-yl]pyridine-3-carboxamide Chemical compound O=C1N(C)C=CC=C1C(=O)NC1=CC=C(\C(=C\C=2NC=CC=2)C(=O)N2)C2=C1 GDYQNHDEYPXVIM-YBEGLDIGSA-N 0.000 claims 1
- 125000006334 2,4-difluoro benzoyl group Chemical group [H]C1=C([H])C(C(*)=O)=C(F)C([H])=C1F 0.000 claims 1
- ZFXGYPBWHHMVKH-UHFFFAOYSA-N 2,4-dimethyl-5-[(2-oxo-1h-indol-3-ylidene)methyl]-n-(2-pyrrolidin-1-ylethyl)-1h-pyrrole-3-carboxamide Chemical compound CC=1NC(C=C2C3=CC=CC=C3NC2=O)=C(C)C=1C(=O)NCCN1CCCC1 ZFXGYPBWHHMVKH-UHFFFAOYSA-N 0.000 claims 1
- UPGCYROFUQYVBB-YVLHZVERSA-N 2,4-dimethyl-5-[(z)-[2-oxo-6-[[4-(trifluoromethyl)benzoyl]carbamoylamino]-1h-indol-3-ylidene]methyl]-1h-pyrrole-3-carboxylic acid Chemical compound OC(=O)C1=C(C)NC(\C=C/2C3=CC=C(NC(=O)NC(=O)C=4C=CC(=CC=4)C(F)(F)F)C=C3NC\2=O)=C1C UPGCYROFUQYVBB-YVLHZVERSA-N 0.000 claims 1
- BAEVZDJJGSYMFZ-WQRHYEAKSA-N 2,4-dimethyl-5-[(z)-[6-[(4-methylbenzoyl)carbamoylamino]-2-oxo-1h-indol-3-ylidene]methyl]-1h-pyrrole-3-carboxylic acid Chemical compound OC(=O)C1=C(C)NC(\C=C/2C3=CC=C(NC(=O)NC(=O)C=4C=CC(C)=CC=4)C=C3NC\2=O)=C1C BAEVZDJJGSYMFZ-WQRHYEAKSA-N 0.000 claims 1
- LLRDETSGCLVZJX-YVLHZVERSA-N 2,4-dimethyl-5-[(z)-[6-[(4-nitrobenzoyl)carbamoylamino]-2-oxo-1h-indol-3-ylidene]methyl]-1h-pyrrole-3-carboxylic acid Chemical compound OC(=O)C1=C(C)NC(\C=C/2C3=CC=C(NC(=O)NC(=O)C=4C=CC(=CC=4)[N+]([O-])=O)C=C3NC\2=O)=C1C LLRDETSGCLVZJX-YVLHZVERSA-N 0.000 claims 1
- SKXDLNXUNKNRGI-CHHVJCJISA-N 2,4-dimethyl-5-[(z)-[6-[(5-methyl-4-oxo-1h-pyridine-3-carbonyl)amino]-2-oxo-1h-indol-3-ylidene]methyl]-1h-pyrrole-3-carboxylic acid Chemical compound OC(=O)C1=C(C)NC(\C=C/2C3=CC=C(NC(=O)C=4C(C(C)=CNC=4)=O)C=C3NC\2=O)=C1C SKXDLNXUNKNRGI-CHHVJCJISA-N 0.000 claims 1
- PQKYFTUPMZXFPP-NVMNQCDNSA-N 2-[5-[(z)-[5-fluoro-6-[(4-methoxybenzoyl)carbamoylamino]-2-oxo-1h-indol-3-ylidene]methyl]-2,4-dimethyl-1h-pyrrol-3-yl]acetic acid Chemical compound C1=CC(OC)=CC=C1C(=O)NC(=O)NC(C(=C1)F)=CC(NC\2=O)=C1C/2=C/C1=C(C)C(CC(O)=O)=C(C)N1 PQKYFTUPMZXFPP-NVMNQCDNSA-N 0.000 claims 1
- RMFKBPSTKOXDKL-ZDLGFXPLSA-N 2-[5-[(z)-[6-[(3-cyclopropyl-2-oxoimidazolidine-1-carbonyl)amino]-2-oxo-1h-indol-3-ylidene]methyl]-2,4-dimethyl-1h-pyrrol-3-yl]acetic acid Chemical compound OC(=O)CC1=C(C)NC(\C=C/2C3=CC=C(NC(=O)N4C(N(C5CC5)CC4)=O)C=C3NC\2=O)=C1C RMFKBPSTKOXDKL-ZDLGFXPLSA-N 0.000 claims 1
- DUBVELBUOAQHGF-QRVIBDJDSA-N 2-[5-[(z)-[6-[[1-(4-fluorophenyl)-2-oxopyridine-3-carbonyl]amino]-2-oxo-1h-indol-3-ylidene]methyl]-2,4-dimethyl-1h-pyrrol-3-yl]acetic acid Chemical compound OC(=O)CC1=C(C)NC(\C=C/2C3=CC=C(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)C=CC=4)=O)C=C3NC\2=O)=C1C DUBVELBUOAQHGF-QRVIBDJDSA-N 0.000 claims 1
- RPELQYLIQDIYJG-FBHDLOMBSA-N 2-[5-[(z)-[6-[[5-(4-fluorophenyl)-4-oxo-1h-pyridine-3-carbonyl]amino]-2-oxo-1h-indol-3-ylidene]methyl]-2,4-dimethyl-1h-pyrrol-3-yl]acetic acid Chemical compound OC(=O)CC1=C(C)NC(\C=C/2C3=CC=C(NC(=O)C=4C(C(C=5C=CC(F)=CC=5)=CNC=4)=O)C=C3NC\2=O)=C1C RPELQYLIQDIYJG-FBHDLOMBSA-N 0.000 claims 1
- OFEKPPBEFBIIGB-UHFFFAOYSA-N 2-[5-[[6-[(4-methoxybenzoyl)carbamoylamino]-2-oxo-1H-indol-3-ylidene]methyl]-2,4-dimethyl-1H-pyrrol-3-yl]acetic acid Chemical compound C1=CC(OC)=CC=C1C(=O)NC(=O)NC1=CC=C(C(=CC2=C(C(CC(O)=O)=C(C)N2)C)C(=O)N2)C2=C1 OFEKPPBEFBIIGB-UHFFFAOYSA-N 0.000 claims 1
- LNGFVQSWMPPJNE-YBEGLDIGSA-N 2-fluoro-n-[[(3z)-2-oxo-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-6-yl]carbamoyl]benzamide Chemical compound FC1=CC=CC=C1C(=O)NC(=O)NC1=CC=C(\C(=C\C=2NC=CC=2)C(=O)N2)C2=C1 LNGFVQSWMPPJNE-YBEGLDIGSA-N 0.000 claims 1
- IMTGEPWWLSLFHI-UHFFFAOYSA-N 2-oxo-1-phenyl-N-(trifluoromethyl)pyridine-3-carboxamide Chemical compound C1(=CC=CC=C1)N1C(C(=CC=C1)C(=O)NC(F)(F)F)=O IMTGEPWWLSLFHI-UHFFFAOYSA-N 0.000 claims 1
- WUOIIWFQKNOPFW-BKUYFWCQSA-N 2-oxo-n-[(3z)-2-oxo-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-6-yl]-1-[4-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1N1C(=O)C(C(=O)NC=2C=C3NC(=O)C(=C\C=4NC=CC=4)/C3=CC=2)=CC=C1 WUOIIWFQKNOPFW-BKUYFWCQSA-N 0.000 claims 1
- UYSFAABBXSRBTC-STZFKDTASA-N 2-oxo-n-[(3z)-2-oxo-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-6-yl]-1-phenylpyridine-3-carboxamide Chemical compound C=1C=CN(C=2C=CC=CC=2)C(=O)C=1C(=O)NC(C=C1NC2=O)=CC=C1\C2=C\C1=CC=CN1 UYSFAABBXSRBTC-STZFKDTASA-N 0.000 claims 1
- DEVUJWRIBVHMPA-UYRXBGFRSA-N 2-oxo-n-[(3z)-2-oxo-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-6-yl]-3-phenylimidazolidine-1-carboxamide Chemical compound C1CN(C=2C=CC=CC=2)C(=O)N1C(=O)NC(C=C1NC2=O)=CC=C1\C2=C\C1=CC=CN1 DEVUJWRIBVHMPA-UYRXBGFRSA-N 0.000 claims 1
- NRXNQPPMTQINNT-DHDCSXOGSA-N 3,4-dichloro-n-[[(3z)-2-oxo-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-6-yl]carbamoyl]benzamide Chemical compound C1=C(Cl)C(Cl)=CC=C1C(=O)NC(=O)NC1=CC=C(\C(=C\C=2NC=CC=2)C(=O)N2)C2=C1 NRXNQPPMTQINNT-DHDCSXOGSA-N 0.000 claims 1
- UPGLQJPWOICJCU-GRSHGNNSSA-N 3,5-dimethoxy-n-[[(3z)-2-oxo-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-6-yl]carbamoyl]benzamide Chemical compound COC1=CC(OC)=CC(C(=O)NC(=O)NC=2C=C3NC(=O)C(=C\C=4NC=CC=4)/C3=CC=2)=C1 UPGLQJPWOICJCU-GRSHGNNSSA-N 0.000 claims 1
- COEOKDJOWYUBTI-WQRHYEAKSA-N 3-(2-fluoro-4-methoxyphenyl)-2-oxo-n-[(3z)-2-oxo-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-6-yl]imidazolidine-1-carboxamide Chemical compound FC1=CC(OC)=CC=C1N1C(=O)N(C(=O)NC=2C=C3NC(=O)C(=C\C=4NC=CC=4)/C3=CC=2)CC1 COEOKDJOWYUBTI-WQRHYEAKSA-N 0.000 claims 1
- XKTLTPAMQWWDLU-ATVHPVEESA-N 3-(2-fluorophenyl)-2-oxo-n-[(3z)-2-oxo-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-6-yl]imidazolidine-1-carboxamide Chemical compound FC1=CC=CC=C1N1C(=O)N(C(=O)NC=2C=C3NC(=O)C(=C\C=4NC=CC=4)/C3=CC=2)CC1 XKTLTPAMQWWDLU-ATVHPVEESA-N 0.000 claims 1
- HQBQMNYPIVLUTB-YVLHZVERSA-N 3-(3,4-dichlorophenyl)-2-oxo-n-[(3z)-2-oxo-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-6-yl]imidazolidine-1-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1N1C(=O)N(C(=O)NC=2C=C3NC(=O)C(=C\C=4NC=CC=4)/C3=CC=2)CC1 HQBQMNYPIVLUTB-YVLHZVERSA-N 0.000 claims 1
- DKUJAZDUABUCLU-UNOMPAQXSA-N 3-(3-chlorophenyl)-2-oxo-n-[(3z)-2-oxo-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-6-yl]imidazolidine-1-carboxamide Chemical compound ClC1=CC=CC(N2C(N(C(=O)NC=3C=C4NC(=O)C(=C\C=5NC=CC=5)/C4=CC=3)CC2)=O)=C1 DKUJAZDUABUCLU-UNOMPAQXSA-N 0.000 claims 1
- KAGKOZRKJNZGTP-UNOMPAQXSA-N 3-(4-chlorophenyl)-2-oxo-n-[(3z)-2-oxo-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-6-yl]imidazolidine-1-carboxamide Chemical compound C1=CC(Cl)=CC=C1N1C(=O)N(C(=O)NC=2C=C3NC(=O)C(=C\C=4NC=CC=4)/C3=CC=2)CC1 KAGKOZRKJNZGTP-UNOMPAQXSA-N 0.000 claims 1
- LCGFAQZFBDVAGS-UNOMPAQXSA-N 3-(4-fluorophenyl)-2-oxo-n-[(3z)-2-oxo-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-6-yl]imidazolidine-1-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(=O)N(C(=O)NC=2C=C3NC(=O)C(=C\C=4NC=CC=4)/C3=CC=2)CC1 LCGFAQZFBDVAGS-UNOMPAQXSA-N 0.000 claims 1
- ZNGPRTKMMBFXON-MOSHPQCFSA-N 3-(4-methoxyphenyl)-2-oxo-n-[(3z)-2-oxo-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-6-yl]imidazolidine-1-carboxamide Chemical compound C1=CC(OC)=CC=C1N1C(=O)N(C(=O)NC=2C=C3NC(=O)C(=C\C=4NC=CC=4)/C3=CC=2)CC1 ZNGPRTKMMBFXON-MOSHPQCFSA-N 0.000 claims 1
- YLVLRAFQLJLIMP-BKUYFWCQSA-N 3-[2,4-dimethyl-5-[(z)-[6-[(3-methylbenzoyl)carbamoylamino]-2-oxo-1h-indol-3-ylidene]methyl]-1h-pyrrol-3-yl]propanoic acid Chemical compound OC(=O)CCC1=C(C)NC(\C=C/2C3=CC=C(NC(=O)NC(=O)C=4C=C(C)C=CC=4)C=C3NC\2=O)=C1C YLVLRAFQLJLIMP-BKUYFWCQSA-N 0.000 claims 1
- PVNBJCYIULZCBN-STZFKDTASA-N 3-[4-(dimethylamino)phenyl]-2-oxo-n-[(3z)-2-oxo-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-6-yl]imidazolidine-1-carboxamide Chemical compound C1=CC(N(C)C)=CC=C1N1C(=O)N(C(=O)NC=2C=C3NC(=O)C(=C\C=4NC=CC=4)/C3=CC=2)CC1 PVNBJCYIULZCBN-STZFKDTASA-N 0.000 claims 1
- XXBBQTICEFSBQM-YVLHZVERSA-N 3-[4-chloro-3-(trifluoromethyl)phenyl]-2-oxo-n-[(3z)-2-oxo-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-6-yl]imidazolidine-1-carboxamide Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(N2C(N(C(=O)NC=3C=C4NC(=O)C(=C\C=5NC=CC=5)/C4=CC=3)CC2)=O)=C1 XXBBQTICEFSBQM-YVLHZVERSA-N 0.000 claims 1
- ZCFACOLFKNPRTA-ZDLGFXPLSA-N 3-[5-[(z)-[5-fluoro-6-[(2-fluoro-4-methoxybenzoyl)carbamoylamino]-2-oxo-1h-indol-3-ylidene]methyl]-2,4-dimethyl-1h-pyrrol-3-yl]propanoic acid Chemical compound FC1=CC(OC)=CC=C1C(=O)NC(=O)NC(C(=C1)F)=CC(NC\2=O)=C1C/2=C/C1=C(C)C(CCC(O)=O)=C(C)N1 ZCFACOLFKNPRTA-ZDLGFXPLSA-N 0.000 claims 1
- OADGTALDOUYOOQ-ODLFYWEKSA-N 3-[5-[(z)-[5-fluoro-6-[(4-methoxybenzoyl)carbamoylamino]-2-oxo-1h-indol-3-ylidene]methyl]-2,4-dimethyl-1h-pyrrol-3-yl]propanoic acid Chemical compound C1=CC(OC)=CC=C1C(=O)NC(=O)NC(C(=C1)F)=CC(NC\2=O)=C1C/2=C/C1=C(C)C(CCC(O)=O)=C(C)N1 OADGTALDOUYOOQ-ODLFYWEKSA-N 0.000 claims 1
- CIDVBRKDJFCKQF-NDENLUEZSA-N 3-[5-[(z)-[6-[(2-fluoro-4-methoxybenzoyl)carbamoylamino]-2-oxo-1h-indol-3-ylidene]methyl]-2,4-dimethyl-1h-pyrrol-3-yl]propanoic acid Chemical compound FC1=CC(OC)=CC=C1C(=O)NC(=O)NC1=CC=C(\C(=C\C2=C(C(CCC(O)=O)=C(C)N2)C)C(=O)N2)C2=C1 CIDVBRKDJFCKQF-NDENLUEZSA-N 0.000 claims 1
- BHBHSMYFMSURRZ-UNOMPAQXSA-N 3-[5-[(z)-[6-[(3-cyclopropyl-2-oxoimidazolidine-1-carbonyl)amino]-2-oxo-1h-indol-3-ylidene]methyl]-2,4-dimethyl-1h-pyrrol-3-yl]propanoic acid Chemical compound OC(=O)CCC1=C(C)NC(\C=C/2C3=CC=C(NC(=O)N4C(N(C5CC5)CC4)=O)C=C3NC\2=O)=C1C BHBHSMYFMSURRZ-UNOMPAQXSA-N 0.000 claims 1
- MFZCFHBDQXUAAX-IWIPYMOSSA-N 3-[5-[(z)-[6-[[1-(4-fluorophenyl)-2-oxopyridine-3-carbonyl]amino]-2-oxo-1h-indol-3-ylidene]methyl]-2,4-dimethyl-1h-pyrrol-3-yl]propanoic acid Chemical compound OC(=O)CCC1=C(C)NC(\C=C/2C3=CC=C(NC(=O)C=4C(N(C=5C=CC(F)=CC=5)C=CC=4)=O)C=C3NC\2=O)=C1C MFZCFHBDQXUAAX-IWIPYMOSSA-N 0.000 claims 1
- LYHCXILGRGEWIO-WQRHYEAKSA-N 3-[5-[(z)-[6-[[4-chloro-3-(trifluoromethyl)benzoyl]carbamoylamino]-2-oxo-1h-indol-3-ylidene]methyl]-2,4-dimethyl-1h-pyrrol-3-yl]propanoic acid Chemical compound OC(=O)CCC1=C(C)NC(\C=C/2C3=CC=C(NC(=O)NC(=O)C=4C=C(C(Cl)=CC=4)C(F)(F)F)C=C3NC\2=O)=C1C LYHCXILGRGEWIO-WQRHYEAKSA-N 0.000 claims 1
- XTSNTQDKODFPFG-NHDPSOOVSA-N 3-[5-[(z)-[6-[[5-(2,4-difluorophenyl)-4-oxo-1h-pyridine-3-carbonyl]amino]-2-oxo-1h-indol-3-ylidene]methyl]-2,4-dimethyl-1h-pyrrol-3-yl]propanoic acid Chemical compound OC(=O)CCC1=C(C)NC(\C=C/2C3=CC=C(NC(=O)C=4C(C(C=5C(=CC(F)=CC=5)F)=CNC=4)=O)C=C3NC\2=O)=C1C XTSNTQDKODFPFG-NHDPSOOVSA-N 0.000 claims 1
- CEGCJMFGMIFCDZ-JJFYIABZSA-N 3-[5-[(z)-[6-[[5-(3,5-difluorophenyl)-4-oxo-1h-pyridine-3-carbonyl]amino]-2-oxo-1h-indol-3-ylidene]methyl]-2,4-dimethyl-1h-pyrrol-3-yl]propanoic acid Chemical compound OC(=O)CCC1=C(C)NC(\C=C/2C3=CC=C(NC(=O)C=4C(C(C=5C=C(F)C=C(F)C=5)=CNC=4)=O)C=C3NC\2=O)=C1C CEGCJMFGMIFCDZ-JJFYIABZSA-N 0.000 claims 1
- DYLAWGPMZRFCKI-UUYOSTAYSA-N 3-[5-[(z)-[6-[[5-(4-fluorophenyl)-4-oxo-1h-pyridine-3-carbonyl]amino]-2-oxo-1h-indol-3-ylidene]methyl]-2,4-dimethyl-1h-pyrrol-3-yl]propanoic acid Chemical compound OC(=O)CCC1=C(C)NC(\C=C/2C3=CC=C(NC(=O)C=4C(C(C=5C=CC(F)=CC=5)=CNC=4)=O)C=C3NC\2=O)=C1C DYLAWGPMZRFCKI-UUYOSTAYSA-N 0.000 claims 1
- DKYPQAKHQXNJLV-YBEGLDIGSA-N 3-cyclopropyl-2-oxo-n-[(3z)-2-oxo-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-6-yl]imidazolidine-1-carboxamide Chemical compound C1CN(C2CC2)C(=O)N1C(=O)NC(C=C1NC2=O)=CC=C1\C2=C\C1=CC=CN1 DKYPQAKHQXNJLV-YBEGLDIGSA-N 0.000 claims 1
- UVRFJUHNZXKRMU-ZSOIEALJSA-N 3-cyclopropyl-n-[(3z)-5-fluoro-2-oxo-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-6-yl]-2-oxoimidazolidine-1-carboxamide Chemical compound O=C1NC=2C=C(NC(=O)N3C(N(C4CC4)CC3)=O)C(F)=CC=2\C1=C\C1=CC=CN1 UVRFJUHNZXKRMU-ZSOIEALJSA-N 0.000 claims 1
- KXMLSCDHVSVRIM-ZROIWOOFSA-N 3-methyl-2-oxo-n-[(3z)-2-oxo-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-6-yl]imidazolidine-1-carboxamide Chemical compound O=C1N(C)CCN1C(=O)NC1=CC=C(\C(=C\C=2NC=CC=2)C(=O)N2)C2=C1 KXMLSCDHVSVRIM-ZROIWOOFSA-N 0.000 claims 1
- GZAJLQWXDGQIMQ-UNOMPAQXSA-N 4-(dimethylamino)-n-[[(3z)-2-oxo-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-6-yl]carbamoyl]benzamide Chemical compound C1=CC(N(C)C)=CC=C1C(=O)NC(=O)NC1=CC=C(\C(=C\C=2NC=CC=2)C(=O)N2)C2=C1 GZAJLQWXDGQIMQ-UNOMPAQXSA-N 0.000 claims 1
- TWGQOAACISTFEJ-DHDCSXOGSA-N 4-chloro-n-[[(3z)-2-oxo-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-6-yl]carbamoyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(C(=O)NC(=O)NC=2C=C3NC(=O)C(=C\C=4NC=CC=4)/C3=CC=2)=C1 TWGQOAACISTFEJ-DHDCSXOGSA-N 0.000 claims 1
- OXLZSXPAMKADPP-YVLHZVERSA-N 4-chloro-n-[[(3z)-2-oxo-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-6-yl]carbamoyl]benzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NC(=O)NC1=CC=C(\C(=C\C=2NC=CC=2)C(=O)N2)C2=C1 OXLZSXPAMKADPP-YVLHZVERSA-N 0.000 claims 1
- PJRGXSUPMHCNGR-VBKFSLOCSA-N 4-methoxy-n-[[(3z)-2-oxo-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-4-yl]carbamoyl]benzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NC(=O)NC1=CC=CC(NC\2=O)=C1C/2=C/C1=CC=CN1 PJRGXSUPMHCNGR-VBKFSLOCSA-N 0.000 claims 1
- SFDUIAVEVJVNFC-WQRHYEAKSA-N 4-methoxy-n-[[(3z)-2-oxo-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-5-yl]carbamoyl]benzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NC(=O)NC1=CC=C(NC(=O)\C2=C/C=3NC=CC=3)C2=C1 SFDUIAVEVJVNFC-WQRHYEAKSA-N 0.000 claims 1
- LBAGNMNWIAWTLK-WQRHYEAKSA-N 4-methoxy-n-[[(3z)-2-oxo-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-6-yl]carbamoyl]benzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NC(=O)NC1=CC=C(\C(=C\C=2NC=CC=2)C(=O)N2)C2=C1 LBAGNMNWIAWTLK-WQRHYEAKSA-N 0.000 claims 1
- XDBJCRBXUIYEQZ-ATVHPVEESA-N 4-methoxy-n-[[(3z)-2-oxo-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-7-yl]carbamoyl]benzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NC(=O)NC1=CC=CC\2=C1NC(=O)C/2=C\C1=CC=CN1 XDBJCRBXUIYEQZ-ATVHPVEESA-N 0.000 claims 1
- GRWHTQYXIXQUOB-WQRHYEAKSA-N 4-methyl-n-[[(3z)-2-oxo-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-6-yl]carbamoyl]benzamide Chemical compound C1=CC(C)=CC=C1C(=O)NC(=O)NC1=CC=C(\C(=C\C=2NC=CC=2)C(=O)N2)C2=C1 GRWHTQYXIXQUOB-WQRHYEAKSA-N 0.000 claims 1
- UBVLTOFGRMWMMO-GRSHGNNSSA-N 4-oxo-n-[(3z)-2-oxo-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-6-yl]-5-[4-(trifluoromethyl)phenyl]-1h-pyridine-3-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C(C1=O)=CNC=C1C(=O)NC1=CC=C(\C(=C\C=2NC=CC=2)C(=O)N2)C2=C1 UBVLTOFGRMWMMO-GRSHGNNSSA-N 0.000 claims 1
- CACUYAFFURLWME-ODLFYWEKSA-N 4-oxo-n-[(3z)-2-oxo-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-6-yl]-5-phenyl-1h-pyridine-3-carboxamide Chemical compound C=1NC=C(C=2C=CC=CC=2)C(=O)C=1C(=O)NC(C=C1NC2=O)=CC=C1\C2=C\C1=CC=CN1 CACUYAFFURLWME-ODLFYWEKSA-N 0.000 claims 1
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| US20100298376A1 (en) | 2009-05-13 | 2010-11-25 | Board Of Regents, The University Of Texas System | Use of novel neuroprotective 3-substituted indolone compositions |
| GB201014374D0 (en) | 2010-08-27 | 2010-10-13 | Univ Greenwich | Novel hybrid compounds |
| CN103179966B (zh) * | 2010-10-08 | 2017-03-15 | 诺瓦提斯公司 | 磺酰胺ns3抑制剂的维生素e制剂 |
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2013
- 2013-04-02 IN IN2105MUN2014 patent/IN2014MN02105A/en unknown
- 2013-04-02 US US13/855,692 patent/US8969361B2/en not_active Expired - Fee Related
- 2013-04-02 ES ES13778039.1T patent/ES2621257T3/es active Active
- 2013-04-02 EP EP13778039.1A patent/EP2838538B1/en not_active Not-in-force
- 2013-04-02 JP JP2015507030A patent/JP6177879B2/ja not_active Expired - Fee Related
- 2013-04-02 WO PCT/US2013/035042 patent/WO2013158367A1/en not_active Ceased
- 2013-04-02 RU RU2014145481A patent/RU2642463C2/ru not_active IP Right Cessation
- 2013-04-02 KR KR1020147032458A patent/KR101774861B1/ko not_active Expired - Fee Related
- 2013-04-02 CN CN201380032742.6A patent/CN104394868A/zh active Pending
- 2013-04-02 AU AU2013249708A patent/AU2013249708B2/en not_active Ceased
- 2013-04-03 ES ES13777764.5T patent/ES2600467T3/es active Active
- 2013-04-03 CN CN201380020494.3A patent/CN104302287B/zh not_active Expired - Fee Related
- 2013-04-03 JP JP2015507031A patent/JP6174119B2/ja not_active Expired - Fee Related
- 2013-04-03 US US13/855,916 patent/US8946282B2/en not_active Expired - Fee Related
- 2013-04-03 KR KR1020147031413A patent/KR101778095B1/ko not_active Expired - Fee Related
- 2013-04-03 RU RU2014145480A patent/RU2627706C2/ru not_active IP Right Cessation
- 2013-04-03 WO PCT/US2013/035177 patent/WO2013158373A1/en not_active Ceased
- 2013-04-03 AU AU2013249714A patent/AU2013249714B2/en not_active Ceased
- 2013-04-03 IN IN2107MUN2014 patent/IN2014MN02107A/en unknown
- 2013-04-03 BR BR112014026182A patent/BR112014026182A2/pt not_active Application Discontinuation
- 2013-04-03 EP EP13777764.5A patent/EP2838531B1/en not_active Not-in-force
- 2013-04-19 TW TW102113981A patent/TWI496784B/zh not_active IP Right Cessation
- 2013-04-19 TW TW102113856A patent/TWI458709B/zh not_active IP Right Cessation
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2014
- 2014-10-19 IL IL235097A patent/IL235097A/en not_active IP Right Cessation
- 2014-10-19 IL IL235098A patent/IL235098A0/en unknown