JP2015500824A5 - - Google Patents
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- JP2015500824A5 JP2015500824A5 JP2014545346A JP2014545346A JP2015500824A5 JP 2015500824 A5 JP2015500824 A5 JP 2015500824A5 JP 2014545346 A JP2014545346 A JP 2014545346A JP 2014545346 A JP2014545346 A JP 2014545346A JP 2015500824 A5 JP2015500824 A5 JP 2015500824A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrrole
- dihydroxy
- methoxyphenyl
- alkyl
- carboxylate
- 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.)
- Pending
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- 150000001875 compounds Chemical class 0.000 claims 51
- 229910052739 hydrogen Inorganic materials 0.000 claims 33
- 239000001257 hydrogen Substances 0.000 claims 33
- -1 3,4-dibutoxy-1,2,5-triphenyl-1H-pyrrole Chemical compound 0.000 claims 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 16
- 239000008194 pharmaceutical composition Substances 0.000 claims 15
- 125000003118 aryl group Chemical group 0.000 claims 14
- 125000001072 heteroaryl group Chemical group 0.000 claims 12
- 125000005843 halogen group Chemical group 0.000 claims 10
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 9
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 8
- 239000000651 prodrug Substances 0.000 claims 8
- 229940002612 prodrug Drugs 0.000 claims 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims 7
- 125000000623 heterocyclic group Chemical group 0.000 claims 7
- LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 claims 7
- 239000012453 solvate Substances 0.000 claims 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 6
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 4
- 239000004480 active ingredient Substances 0.000 claims 4
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 4
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 3
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 3
- 208000035143 Bacterial infection Diseases 0.000 claims 3
- 208000022362 bacterial infectious disease Diseases 0.000 claims 3
- 230000003115 biocidal effect Effects 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- RFIOZSIHFNEKFF-UHFFFAOYSA-M piperazine-1-carboxylate Chemical compound [O-]C(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-M 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 2
- 241000193738 Bacillus anthracis Species 0.000 claims 2
- 241000894006 Bacteria Species 0.000 claims 2
- 241000186781 Listeria Species 0.000 claims 2
- 241000193998 Streptococcus pneumoniae Species 0.000 claims 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 2
- 150000001241 acetals Chemical class 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims 2
- FMQVJAPGSVCECP-UHFFFAOYSA-N diethyl 3,4-dihydroxy-1-(4-methoxyphenyl)pyrrole-2,5-dicarboxylate Chemical compound CCOC(=O)C1=C(O)C(O)=C(C(=O)OCC)N1C1=CC=C(OC)C=C1 FMQVJAPGSVCECP-UHFFFAOYSA-N 0.000 claims 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 2
- VGNWOFPNOVAHOE-UHFFFAOYSA-N ethyl 3-diethoxyphosphoryloxy-5-(dimethylcarbamoyl)-4-hydroxy-1-(4-methoxyphenyl)pyrrole-2-carboxylate Chemical compound CCOC(=O)c1c(OP(=O)(OCC)OCC)c(O)c(C(=O)N(C)C)n1-c1ccc(OC)cc1 VGNWOFPNOVAHOE-UHFFFAOYSA-N 0.000 claims 2
- DSGYDCBOQWWSEA-UHFFFAOYSA-N ethyl 5-(dimethylcarbamoyl)-3,4-dihydroxy-1-(4-methoxyphenyl)pyrrole-2-carboxylate Chemical compound CCOC(=O)C1=C(O)C(O)=C(C(=O)N(C)C)N1C1=CC=C(OC)C=C1 DSGYDCBOQWWSEA-UHFFFAOYSA-N 0.000 claims 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 229940031000 streptococcus pneumoniae Drugs 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- 150000003952 β-lactams Chemical class 0.000 claims 2
- PIZVVTVJCRYWKC-UHFFFAOYSA-N (2,6-dimethylcyclohexyl) 5-(dimethylcarbamoyl)-3,4-dihydroxy-1-(4-methoxyphenyl)pyrrole-2-carboxylate Chemical compound C1=CC(OC)=CC=C1N1C(C(=O)N(C)C)=C(O)C(O)=C1C(=O)OC1C(C)CCCC1C PIZVVTVJCRYWKC-UHFFFAOYSA-N 0.000 claims 1
- GGWXJENHOMSQKF-UHFFFAOYSA-N 1-(2-methoxyphenyl)-2-n,2-n,5-n,5-n-tetramethyl-3,4-bis(phenylmethoxy)pyrrole-2,5-dicarboxamide Chemical compound COC1=CC=CC=C1N1C(C(=O)N(C)C)=C(OCC=2C=CC=CC=2)C(OCC=2C=CC=CC=2)=C1C(=O)N(C)C GGWXJENHOMSQKF-UHFFFAOYSA-N 0.000 claims 1
- GBHQRRAPCIPUGZ-UHFFFAOYSA-N 1-(4-ethoxyphenyl)-2-n,2-n,5-n,5-n-tetraethyl-3,4-bis(phenylmethoxy)pyrrole-2,5-dicarboxamide Chemical compound C1=CC(OCC)=CC=C1N1C(C(=O)N(CC)CC)=C(OCC=2C=CC=CC=2)C(OCC=2C=CC=CC=2)=C1C(=O)N(CC)CC GBHQRRAPCIPUGZ-UHFFFAOYSA-N 0.000 claims 1
- BUROUEYQJNZHGV-UHFFFAOYSA-N 1-(4-ethoxyphenyl)-2-n,2-n,5-n,5-n-tetraethyl-3,4-dihydroxypyrrole-2,5-dicarboxamide Chemical compound C1=CC(OCC)=CC=C1N1C(C(=O)N(CC)CC)=C(O)C(O)=C1C(=O)N(CC)CC BUROUEYQJNZHGV-UHFFFAOYSA-N 0.000 claims 1
- HJTQFKHMMYPOFT-UHFFFAOYSA-N 1-(4-ethoxyphenyl)-2-n,2-n,5-n,5-n-tetramethyl-3,4-bis(phenylmethoxy)pyrrole-2,5-dicarboxamide Chemical compound C1=CC(OCC)=CC=C1N1C(C(=O)N(C)C)=C(OCC=2C=CC=CC=2)C(OCC=2C=CC=CC=2)=C1C(=O)N(C)C HJTQFKHMMYPOFT-UHFFFAOYSA-N 0.000 claims 1
- JXQFJDCZOCJXPJ-UHFFFAOYSA-N 1-(4-ethoxyphenyl)-2-n,5-n-diethyl-3,4-dihydroxypyrrole-2,5-dicarboxamide Chemical compound CCNC(=O)C1=C(O)C(O)=C(C(=O)NCC)N1C1=CC=C(OCC)C=C1 JXQFJDCZOCJXPJ-UHFFFAOYSA-N 0.000 claims 1
- NJIUTCOWMDMOBP-UHFFFAOYSA-N 1-(4-ethoxyphenyl)-3,4-dihydroxy-2-n,2-n,5-n,5-n-tetramethylpyrrole-2,5-dicarboxamide Chemical compound C1=CC(OCC)=CC=C1N1C(C(=O)N(C)C)=C(O)C(O)=C1C(=O)N(C)C NJIUTCOWMDMOBP-UHFFFAOYSA-N 0.000 claims 1
- XUDHEDLJBBQCQI-UHFFFAOYSA-N 1-(4-ethoxyphenyl)-3,4-dihydroxypyrrole-2,5-dicarboxamide Chemical compound C1=CC(OCC)=CC=C1N1C(C(N)=O)=C(O)C(O)=C1C(N)=O XUDHEDLJBBQCQI-UHFFFAOYSA-N 0.000 claims 1
- ZZDUTDMZQXGMCG-UHFFFAOYSA-N 1-(4-fluorophenyl)-3,4-bis(phenylmethoxy)pyrrole-2,5-dicarboxamide Chemical compound C=1C=CC=CC=1COC1=C(C(N)=O)N(C=2C=CC(F)=CC=2)C(C(=O)N)=C1OCC1=CC=CC=C1 ZZDUTDMZQXGMCG-UHFFFAOYSA-N 0.000 claims 1
- YVOWDUCUGHQQJJ-UHFFFAOYSA-N 1-(4-fluorophenyl)-3,4-dihydroxy-2-n,2-n,5-n,5-n-tetra(propan-2-yl)pyrrole-2,5-dicarboxamide Chemical compound CC(C)N(C(C)C)C(=O)C1=C(O)C(O)=C(C(=O)N(C(C)C)C(C)C)N1C1=CC=C(F)C=C1 YVOWDUCUGHQQJJ-UHFFFAOYSA-N 0.000 claims 1
- ZBJUSVVQRJDSGX-UHFFFAOYSA-N 1-(4-fluorophenyl)-3,4-dihydroxy-2-n,2-n,5-n,5-n-tetramethylpyrrole-2,5-dicarboxamide Chemical compound CN(C)C(=O)C1=C(O)C(O)=C(C(=O)N(C)C)N1C1=CC=C(F)C=C1 ZBJUSVVQRJDSGX-UHFFFAOYSA-N 0.000 claims 1
- QZTZTGCDGKRSDH-UHFFFAOYSA-N 1-(4-fluorophenyl)-3,4-dihydroxy-2-n,5-n-dimethyl-2-n,5-n-di(propan-2-yl)pyrrole-2,5-dicarboxamide Chemical compound CC(C)N(C)C(=O)C1=C(O)C(O)=C(C(=O)N(C)C(C)C)N1C1=CC=C(F)C=C1 QZTZTGCDGKRSDH-UHFFFAOYSA-N 0.000 claims 1
- QMBAYVKQWUOPLP-UHFFFAOYSA-N 1-(4-fluorophenyl)-3,4-dihydroxy-2-n,5-n-dimethyl-2-n,5-n-diphenylpyrrole-2,5-dicarboxamide Chemical compound C=1C=CC=CC=1N(C)C(=O)C(N1C=2C=CC(F)=CC=2)=C(O)C(O)=C1C(=O)N(C)C1=CC=CC=C1 QMBAYVKQWUOPLP-UHFFFAOYSA-N 0.000 claims 1
- ONCYLCLHYYNRTG-UHFFFAOYSA-N 1-(4-fluorophenyl)-3,4-dihydroxypyrrole-2,5-dicarboxamide Chemical compound NC(=O)C1=C(O)C(O)=C(C(N)=O)N1C1=CC=C(F)C=C1 ONCYLCLHYYNRTG-UHFFFAOYSA-N 0.000 claims 1
- KWUBPEPBIOWVDV-UHFFFAOYSA-N 1-(4-methoxyphenyl)-2-n,2-n,5-n,5-n-tetramethyl-3,4-bis(phenylmethoxy)pyrrole-2,5-dicarboxamide Chemical compound C1=CC(OC)=CC=C1N1C(C(=O)N(C)C)=C(OCC=2C=CC=CC=2)C(OCC=2C=CC=CC=2)=C1C(=O)N(C)C KWUBPEPBIOWVDV-UHFFFAOYSA-N 0.000 claims 1
- VPXNJGQRXSIRFI-UHFFFAOYSA-N 1-(4-methoxyphenyl)-3,4-bis(phenylmethoxy)pyrrole-2,5-dicarboxamide Chemical compound C1=CC(OC)=CC=C1N1C(C(N)=O)=C(OCC=2C=CC=CC=2)C(OCC=2C=CC=CC=2)=C1C(N)=O VPXNJGQRXSIRFI-UHFFFAOYSA-N 0.000 claims 1
- VOKBSFHJZWOGJQ-UHFFFAOYSA-N 1-(4-methoxyphenyl)-n,n-dimethyl-3,4-bis(phenylmethoxy)-5-(piperidine-1-carbonyl)pyrrole-2-carboxamide Chemical compound C1=CC(OC)=CC=C1N1C(C(=O)N2CCCCC2)=C(OCC=2C=CC=CC=2)C(OCC=2C=CC=CC=2)=C1C(=O)N(C)C VOKBSFHJZWOGJQ-UHFFFAOYSA-N 0.000 claims 1
- PLDJSFMGOQBRDF-UHFFFAOYSA-N 1-(4-methoxyphenyl)-n,n-dimethyl-5-(4-methylpiperazine-1-carbonyl)-3,4-bis(phenylmethoxy)pyrrole-2-carboxamide Chemical compound C1=CC(OC)=CC=C1N1C(C(=O)N2CCN(C)CC2)=C(OCC=2C=CC=CC=2)C(OCC=2C=CC=CC=2)=C1C(=O)N(C)C PLDJSFMGOQBRDF-UHFFFAOYSA-N 0.000 claims 1
- MSSYTIJSIYAKOP-UHFFFAOYSA-N 1-(4-methoxyphenyl)-n,n-dimethyl-5-(morpholine-4-carbonyl)-3,4-bis(phenylmethoxy)pyrrole-2-carboxamide Chemical compound C1=CC(OC)=CC=C1N1C(C(=O)N2CCOCC2)=C(OCC=2C=CC=CC=2)C(OCC=2C=CC=CC=2)=C1C(=O)N(C)C MSSYTIJSIYAKOP-UHFFFAOYSA-N 0.000 claims 1
- QRVFJNBUWPNVII-UHFFFAOYSA-N 1-[4-(dimethylcarbamoyl)phenyl]-3,4-dihydroxy-2-n,2-n,5-n,5-n-tetramethylpyrrole-2,5-dicarboxamide Chemical compound CN(C)C(=O)C1=C(O)C(O)=C(C(=O)N(C)C)N1C1=CC=C(C(=O)N(C)C)C=C1 QRVFJNBUWPNVII-UHFFFAOYSA-N 0.000 claims 1
- XSFBYONTFLQODU-UHFFFAOYSA-N 2,2-dimethylpropyl 5-(dimethylcarbamoyl)-3,4-dihydroxy-1-(4-methoxyphenyl)pyrrole-2-carboxylate Chemical compound COc1ccc(cc1)-n1c(C(=O)OCC(C)(C)C)c(O)c(O)c1C(=O)N(C)C XSFBYONTFLQODU-UHFFFAOYSA-N 0.000 claims 1
- PMLRKSWISJJURS-UHFFFAOYSA-N 2-[4-(2-carboxypropan-2-yl)-2,5-bis(dimethylcarbamoyl)-1-(4-methoxyphenyl)pyrrol-3-yl]-2-methylpropanoic acid Chemical compound CC(C)(C1=C(N(C(=C1C(C)(C)C(=O)O)C(=O)N(C)C)C2=CC=C(C=C2)OC)C(=O)N(C)C)C(=O)O PMLRKSWISJJURS-UHFFFAOYSA-N 0.000 claims 1
- SPXXQEAGOZGEBY-UHFFFAOYSA-N 2-n,2-n,5-n,5-n-tetraethyl-1-(4-methoxyphenyl)-3,4-bis(phenylmethoxy)pyrrole-2,5-dicarboxamide Chemical compound C=1C=CC=CC=1COC1=C(C(=O)N(CC)CC)N(C=2C=CC(OC)=CC=2)C(C(=O)N(CC)CC)=C1OCC1=CC=CC=C1 SPXXQEAGOZGEBY-UHFFFAOYSA-N 0.000 claims 1
- KMQCPIGRQAFTNW-UHFFFAOYSA-N 2-n,2-n,5-n,5-n-tetraethyl-3,4-dihydroxy-1-(4-methoxyphenyl)pyrrole-2,5-dicarboxamide Chemical compound CCN(CC)C(=O)C1=C(O)C(O)=C(C(=O)N(CC)CC)N1C1=CC=C(OC)C=C1 KMQCPIGRQAFTNW-UHFFFAOYSA-N 0.000 claims 1
- SHQHPAYCEWSFGW-UHFFFAOYSA-N 2-n,2-n,5-n,5-n-tetramethyl-3,4-bis(phenylmethoxy)-1-[4-(trifluoromethyl)phenyl]pyrrole-2,5-dicarboxamide Chemical compound C=1C=CC=CC=1COC1=C(C(=O)N(C)C)N(C=2C=CC(=CC=2)C(F)(F)F)C(C(=O)N(C)C)=C1OCC1=CC=CC=C1 SHQHPAYCEWSFGW-UHFFFAOYSA-N 0.000 claims 1
- GVOURTQHNRLYBW-UHFFFAOYSA-N 2-n,5-n-diethyl-1-(4-methoxyphenyl)-3,4-bis(phenylmethoxy)pyrrole-2,5-dicarboxamide Chemical compound C=1C=CC=CC=1COC1=C(C(=O)NCC)N(C=2C=CC(OC)=CC=2)C(C(=O)NCC)=C1OCC1=CC=CC=C1 GVOURTQHNRLYBW-UHFFFAOYSA-N 0.000 claims 1
- DVQAQRWAGJBXOP-UHFFFAOYSA-N 3,4-dihydroxy-1-(2-methoxyphenyl)-2-n,2-n,5-n,5-n-tetramethylpyrrole-2,5-dicarboxamide Chemical compound COC1=CC=CC=C1N1C(C(=O)N(C)C)=C(O)C(O)=C1C(=O)N(C)C DVQAQRWAGJBXOP-UHFFFAOYSA-N 0.000 claims 1
- JOECWWZBDPISPH-UHFFFAOYSA-N 3,4-dihydroxy-1-(4-methoxyphenyl)-2-n,2-n,5-n,5-n-tetramethylpyrrole-2,5-dicarboxamide Chemical compound C1=CC(OC)=CC=C1N1C(C(=O)N(C)C)=C(O)C(O)=C1C(=O)N(C)C JOECWWZBDPISPH-UHFFFAOYSA-N 0.000 claims 1
- WEDPCOCBPAHNRA-UHFFFAOYSA-N 3,4-dihydroxy-1-(4-methoxyphenyl)-n,n-dimethyl-5-(4-methylpiperazine-1-carbonyl)pyrrole-2-carboxamide Chemical compound C1=CC(OC)=CC=C1N1C(C(=O)N2CCN(C)CC2)=C(O)C(O)=C1C(=O)N(C)C WEDPCOCBPAHNRA-UHFFFAOYSA-N 0.000 claims 1
- UOQOGHVYPSKNFX-UHFFFAOYSA-N 3,4-dihydroxy-1-(4-methoxyphenyl)-n,n-dimethyl-5-(morpholine-4-carbonyl)pyrrole-2-carboxamide Chemical compound C1=CC(OC)=CC=C1N1C(C(=O)N2CCOCC2)=C(O)C(O)=C1C(=O)N(C)C UOQOGHVYPSKNFX-UHFFFAOYSA-N 0.000 claims 1
- WVDRGZSXXNAHIM-UHFFFAOYSA-N 3,4-dihydroxy-1-(4-methoxyphenyl)-n,n-dimethyl-5-(piperidine-1-carbonyl)pyrrole-2-carboxamide Chemical compound C1=CC(OC)=CC=C1N1C(C(=O)N2CCCCC2)=C(O)C(O)=C1C(=O)N(C)C WVDRGZSXXNAHIM-UHFFFAOYSA-N 0.000 claims 1
- VTOUAFDEQWTHCP-UHFFFAOYSA-N 3,4-dihydroxy-1-(4-methoxyphenyl)pyrrole-2,5-dicarbonitrile Chemical compound C1=CC(OC)=CC=C1N1C(C#N)=C(O)C(O)=C1C#N VTOUAFDEQWTHCP-UHFFFAOYSA-N 0.000 claims 1
- XGGQBWAPZNKQDN-UHFFFAOYSA-N 3,4-dihydroxy-1-(4-methoxyphenyl)pyrrole-2,5-dicarboxamide Chemical compound C1=CC(OC)=CC=C1N1C(C(N)=O)=C(O)C(O)=C1C(N)=O XGGQBWAPZNKQDN-UHFFFAOYSA-N 0.000 claims 1
- UMFMGHXREKZXGB-UHFFFAOYSA-N 3,4-dihydroxy-2-n,2-n,5-n,5-n-tetramethyl-1-[4-(trifluoromethyl)phenyl]pyrrole-2,5-dicarboxamide Chemical compound CN(C)C(=O)C1=C(O)C(O)=C(C(=O)N(C)C)N1C1=CC=C(C(F)(F)F)C=C1 UMFMGHXREKZXGB-UHFFFAOYSA-N 0.000 claims 1
- LMGVWCVJXZBBFO-UHFFFAOYSA-N 3,4-dimethoxy-1-(4-methylphenyl)-2,5-diphenylpyrrole Chemical compound C=1C=C(C)C=CC=1N1C(C=2C=CC=CC=2)=C(OC)C(OC)=C1C1=CC=CC=C1 LMGVWCVJXZBBFO-UHFFFAOYSA-N 0.000 claims 1
- SMBKTARVADHYBC-UHFFFAOYSA-N 3-[4-(2-carboxy-2-methylpropyl)-2-(dimethylcarbamoyl)-5-ethoxycarbonyl-1-(4-methoxyphenyl)pyrrol-3-yl]-2,2-dimethylpropanoic acid Chemical compound CCOC(=O)C1=C(CC(C)(C)C(O)=O)C(CC(C)(C)C(O)=O)=C(C(=O)N(C)C)N1C1=CC=C(OC)C=C1 SMBKTARVADHYBC-UHFFFAOYSA-N 0.000 claims 1
- AAZUGUANVDRRFV-UHFFFAOYSA-N 3-[4-[2-(dimethylcarbamoyl)-5-ethoxycarbonyl-3,4-dihydroxypyrrol-1-yl]phenoxy]propylphosphonic acid Chemical compound CCOC(=O)c1c(O)c(O)c(C(=O)N(C)C)n1-c1ccc(OCCCP(O)(O)=O)cc1 AAZUGUANVDRRFV-UHFFFAOYSA-N 0.000 claims 1
- KWNLCFHVCZWDEY-UHFFFAOYSA-N 4-[2-[4-[1-(1-carboxypiperidin-4-yl)piperidin-2-yl]-2-(dimethylcarbamoyl)-5-ethoxycarbonyl-1-(4-methoxyphenyl)pyrrol-3-yl]piperidin-1-yl]piperidine-1-carboxylic acid Chemical compound CCOC(=O)C1=C(C(=C(N1C2=CC=C(C=C2)OC)C(=O)N(C)C)C3CCCCN3C4CCN(CC4)C(=O)O)C5CCCCN5C6CCN(CC6)C(=O)O KWNLCFHVCZWDEY-UHFFFAOYSA-N 0.000 claims 1
- FWPMOWFCZPJQLC-UHFFFAOYSA-N 5-N,2-dibenzyl-1-(4-fluorophenyl)-3,4-dihydroxy-2-N,5-N-dimethyl-3H-pyrrole-2,5-dicarboxamide Chemical compound C(C1=CC=CC=C1)C1(N(C(=C(C1O)O)C(=O)N(C)CC1=CC=CC=C1)C1=CC=C(C=C1)F)C(=O)NC FWPMOWFCZPJQLC-UHFFFAOYSA-N 0.000 claims 1
- VYUKIORTVYLDDL-UHFFFAOYSA-N 5-acetyl-3,4-dihydroxy-1-(4-methoxyphenyl)-n,n-dimethylpyrrole-2-carboxamide Chemical compound C1=CC(OC)=CC=C1N1C(C(=O)N(C)C)=C(O)C(O)=C1C(C)=O VYUKIORTVYLDDL-UHFFFAOYSA-N 0.000 claims 1
- ZQZQKHRCANHASA-UHFFFAOYSA-N 5-cyano-1-(4-fluorophenyl)-n,n-dimethyl-3,4-bis(phenylmethoxy)pyrrole-2-carboxamide Chemical compound C=1C=CC=CC=1COC1=C(C#N)N(C=2C=CC(F)=CC=2)C(C(=O)N(C)C)=C1OCC1=CC=CC=C1 ZQZQKHRCANHASA-UHFFFAOYSA-N 0.000 claims 1
- MPSINJQOYWDDEJ-UHFFFAOYSA-N 5-cyano-3,4-dihydroxy-1-(4-methoxyphenyl)-n,n-dimethylpyrrole-2-carboxamide Chemical compound C1=CC(OC)=CC=C1N1C(C(=O)N(C)C)=C(O)C(O)=C1C#N MPSINJQOYWDDEJ-UHFFFAOYSA-N 0.000 claims 1
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- FOGCUJWGZKTTCJ-UHFFFAOYSA-N dimethyl 3,4-dihydroxy-1-phenylpyrrole-2,5-dicarboxylate Chemical compound COC(=O)C1=C(O)C(O)=C(C(=O)OC)N1C1=CC=CC=C1 FOGCUJWGZKTTCJ-UHFFFAOYSA-N 0.000 claims 1
- HKLFPQMNKYONQX-UHFFFAOYSA-N dipropan-2-yl 3,4-dihydroxy-1-(4-methoxyphenyl)pyrrole-2,5-dicarboxylate Chemical compound C1=CC(OC)=CC=C1N1C(C(=O)OC(C)C)=C(O)C(O)=C1C(=O)OC(C)C HKLFPQMNKYONQX-UHFFFAOYSA-N 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- YMQJWPSLYXOGMN-UHFFFAOYSA-N ditert-butyl 3,4-dihydroxy-1-(4-methoxyphenyl)pyrrole-2,5-dicarboxylate Chemical compound C1=CC(OC)=CC=C1N1C(C(=O)OC(C)(C)C)=C(O)C(O)=C1C(=O)OC(C)(C)C YMQJWPSLYXOGMN-UHFFFAOYSA-N 0.000 claims 1
- LBZUTQSXPRDNKJ-UHFFFAOYSA-N ditert-butyl 3,4-dihydroxy-1-(4-nitrophenyl)pyrrole-2,5-dicarboxylate Chemical compound CC(C)(C)OC(=O)C1=C(O)C(O)=C(C(=O)OC(C)(C)C)N1C1=CC=C([N+]([O-])=O)C=C1 LBZUTQSXPRDNKJ-UHFFFAOYSA-N 0.000 claims 1
- 206010014599 encephalitis Diseases 0.000 claims 1
- BAMAEFPMBWZISW-UHFFFAOYSA-N ethyl 1-(4-methoxyphenyl)-3,4-bis(phenylmethoxy)-5-(2h-tetrazol-5-yl)pyrrole-2-carboxylate Chemical compound C=1C=CC=CC=1COC1=C(C2=NNN=N2)N(C=2C=CC(OC)=CC=2)C(C(=O)OCC)=C1OCC1=CC=CC=C1 BAMAEFPMBWZISW-UHFFFAOYSA-N 0.000 claims 1
- ZVELVOLBNZLUNJ-UHFFFAOYSA-N ethyl 1-(4-methoxyphenyl)-3,4-bis(phenylmethoxy)-5-pyridin-2-ylpyrrole-2-carboxylate Chemical compound C=1C=CC=CC=1COC1=C(C=2N=CC=CC=2)N(C=2C=CC(OC)=CC=2)C(C(=O)OCC)=C1OCC1=CC=CC=C1 ZVELVOLBNZLUNJ-UHFFFAOYSA-N 0.000 claims 1
- AWZXSCQLJRVKJX-UHFFFAOYSA-N ethyl 1-(4-methoxyphenyl)-3,4-bis(phenylmethoxy)-5-pyridin-3-ylpyrrole-2-carboxylate Chemical compound C=1C=CC=CC=1COC1=C(C=2C=NC=CC=2)N(C=2C=CC(OC)=CC=2)C(C(=O)OCC)=C1OCC1=CC=CC=C1 AWZXSCQLJRVKJX-UHFFFAOYSA-N 0.000 claims 1
- CEDPAGLENFJWMQ-UHFFFAOYSA-N ethyl 1-(4-methoxyphenyl)-3,4-bis(phenylmethoxy)-5-pyridin-4-ylpyrrole-2-carboxylate Chemical compound C=1C=CC=CC=1COC1=C(C=2C=CN=CC=2)N(C=2C=CC(OC)=CC=2)C(C(=O)OCC)=C1OCC1=CC=CC=C1 CEDPAGLENFJWMQ-UHFFFAOYSA-N 0.000 claims 1
- FLBFZCDJGLIQIQ-UHFFFAOYSA-N ethyl 1-(4-methoxyphenyl)-5-(5-methyl-1,3,4-oxadiazol-2-yl)-3,4-bis(phenylmethoxy)pyrrole-2-carboxylate Chemical compound C=1C=CC=CC=1COC1=C(C=2OC(C)=NN=2)N(C=2C=CC(OC)=CC=2)C(C(=O)OCC)=C1OCC1=CC=CC=C1 FLBFZCDJGLIQIQ-UHFFFAOYSA-N 0.000 claims 1
- XBXWSVWOBHMTPX-UHFFFAOYSA-N ethyl 1-[4-(3-diethoxyphosphorylpropoxy)phenyl]-5-(dimethylcarbamoyl)-3,4-dihydroxypyrrole-2-carboxylate Chemical compound CCOC(=O)c1c(O)c(O)c(C(=O)N(C)C)n1-c1ccc(OCCCP(=O)(OCC)OCC)cc1 XBXWSVWOBHMTPX-UHFFFAOYSA-N 0.000 claims 1
- WYTXKMSTRYUIHN-UHFFFAOYSA-N ethyl 3,4-bis(diethoxyphosphoryloxy)-5-(dimethylcarbamoyl)-1-(4-methoxyphenyl)pyrrole-2-carboxylate Chemical compound CCOC(=O)C1=C(OP(=O)(OCC)OCC)C(OP(=O)(OCC)OCC)=C(C(=O)N(C)C)N1C1=CC=C(OC)C=C1 WYTXKMSTRYUIHN-UHFFFAOYSA-N 0.000 claims 1
- DHBJGQVXIDDTTC-UHFFFAOYSA-N ethyl 3,4-diacetyloxy-5-(dimethylcarbamoyl)-1-(4-methoxyphenyl)pyrrole-2-carboxylate Chemical compound CCOC(=O)C1=C(OC(C)=O)C(OC(C)=O)=C(C(=O)N(C)C)N1C1=CC=C(OC)C=C1 DHBJGQVXIDDTTC-UHFFFAOYSA-N 0.000 claims 1
- TVFBWRFTZRYEQM-UHFFFAOYSA-N ethyl 3,4-dihydroxy-1-(4-methoxyphenyl)-5-(2H-tetrazol-5-yl)pyrrole-2-carboxylate Chemical compound CCOC(=O)c1c(O)c(O)c(-c2nn[nH]n2)n1-c1ccc(OC)cc1 TVFBWRFTZRYEQM-UHFFFAOYSA-N 0.000 claims 1
- KRTAVIQVPAFLND-UHFFFAOYSA-N ethyl 3,4-dihydroxy-1-(4-methoxyphenyl)-5-(4-methylpiperazine-1-carbonyl)pyrrole-2-carboxylate Chemical compound C=1C=C(OC)C=CC=1N1C(C(=O)OCC)=C(O)C(O)=C1C(=O)N1CCN(C)CC1 KRTAVIQVPAFLND-UHFFFAOYSA-N 0.000 claims 1
- RLADPQONVGGUPG-UHFFFAOYSA-N ethyl 3,4-dihydroxy-1-(4-methoxyphenyl)-5-(methylcarbamoyl)pyrrole-2-carboxylate Chemical compound CCOC(=O)c1c(O)c(O)c(C(=O)NC)n1-c1ccc(OC)cc1 RLADPQONVGGUPG-UHFFFAOYSA-N 0.000 claims 1
- LFWMRWQGJVHFLJ-UHFFFAOYSA-N ethyl 3,4-dihydroxy-1-(4-methoxyphenyl)-5-(morpholine-4-carbonyl)pyrrole-2-carboxylate Chemical compound C=1C=C(OC)C=CC=1N1C(C(=O)OCC)=C(O)C(O)=C1C(=O)N1CCOCC1 LFWMRWQGJVHFLJ-UHFFFAOYSA-N 0.000 claims 1
- DWTBDNSKLIKOGT-UHFFFAOYSA-N ethyl 3,4-dihydroxy-1-(4-methoxyphenyl)-5-pyridin-2-ylpyrrole-2-carboxylate Chemical compound CCOC(=O)c1c(O)c(O)c(-c2ccccn2)n1-c1ccc(OC)cc1 DWTBDNSKLIKOGT-UHFFFAOYSA-N 0.000 claims 1
- QTGUERDQURTWMP-UHFFFAOYSA-N ethyl 4-diethoxyphosphoryloxy-5-(dimethylcarbamoyl)-3-hydroxy-1-(4-methoxyphenyl)pyrrole-2-carboxylate Chemical compound CCOC(=O)c1c(O)c(OP(=O)(OCC)OCC)c(C(=O)N(C)C)n1-c1ccc(OC)cc1 QTGUERDQURTWMP-UHFFFAOYSA-N 0.000 claims 1
- FBQNZCXZZJCGNG-UHFFFAOYSA-N ethyl 5-(2-methoxyphenyl)-1-(4-methoxyphenyl)-3,4-bis(phenylmethoxy)pyrrole-2-carboxylate Chemical compound C=1C=CC=CC=1COC1=C(C=2C(=CC=CC=2)OC)N(C=2C=CC(OC)=CC=2)C(C(=O)OCC)=C1OCC1=CC=CC=C1 FBQNZCXZZJCGNG-UHFFFAOYSA-N 0.000 claims 1
- ZIGYJWNJTXPBAM-UHFFFAOYSA-N ethyl 5-(4-ethyl-1,3-thiazol-2-yl)-3,4-dihydroxy-1-(4-methoxyphenyl)pyrrole-2-carboxylate Chemical compound CCOC(=O)c1c(O)c(O)c(-c2nc(CC)cs2)n1-c1ccc(OC)cc1 ZIGYJWNJTXPBAM-UHFFFAOYSA-N 0.000 claims 1
- NWCPQDVYWMQRSY-UHFFFAOYSA-N ethyl 5-(5-ethyl-1,3,4-oxadiazol-2-yl)-1-(4-methoxyphenyl)-3,4-bis(phenylmethoxy)pyrrole-2-carboxylate Chemical compound C=1C=CC=CC=1COC1=C(C=2OC(CC)=NN=2)N(C=2C=CC(OC)=CC=2)C(C(=O)OCC)=C1OCC1=CC=CC=C1 NWCPQDVYWMQRSY-UHFFFAOYSA-N 0.000 claims 1
- KWESGDQFDJCDBF-UHFFFAOYSA-N ethyl 5-(dibutylcarbamoyl)-3,4-dihydroxy-1-(4-methoxyphenyl)pyrrole-2-carboxylate Chemical compound CCCCN(CCCC)C(=O)C1=C(O)C(O)=C(C(=O)OCC)N1C1=CC=C(OC)C=C1 KWESGDQFDJCDBF-UHFFFAOYSA-N 0.000 claims 1
- PXYDLKSLNDQICJ-UHFFFAOYSA-N ethyl 5-(diethylcarbamoyl)-3,4-dihydroxy-1-(4-methoxyphenyl)pyrrole-2-carboxylate Chemical compound CCOC(=O)C1=C(O)C(O)=C(C(=O)N(CC)CC)N1C1=CC=C(OC)C=C1 PXYDLKSLNDQICJ-UHFFFAOYSA-N 0.000 claims 1
- FUYBAWSWHFMXED-UHFFFAOYSA-N ethyl 5-(dimethylcarbamoyl)-1-(4-fluorophenyl)-3,4-dihydroxypyrrole-2-carboxylate Chemical compound CCOC(=O)C1=C(O)C(O)=C(C(=O)N(C)C)N1C1=CC=C(F)C=C1 FUYBAWSWHFMXED-UHFFFAOYSA-N 0.000 claims 1
- KBTPQRHAFMOINT-UHFFFAOYSA-N ethyl 5-(dimethylcarbamoyl)-1-(4-iodophenyl)-3,4-bis(phenylmethoxy)pyrrole-2-carboxylate Chemical compound C=1C=CC=CC=1COC1=C(C(=O)N(C)C)N(C=2C=CC(I)=CC=2)C(C(=O)OCC)=C1OCC1=CC=CC=C1 KBTPQRHAFMOINT-UHFFFAOYSA-N 0.000 claims 1
- WTPPJTBHISKRRV-UHFFFAOYSA-N ethyl 5-(dimethylcarbamoyl)-1-(4-methoxyphenyl)-3,4-bis(3-methoxypropanoyloxy)pyrrole-2-carboxylate Chemical compound CCOC(=O)C1=C(OC(=O)CCOC)C(OC(=O)CCOC)=C(C(=O)N(C)C)N1C1=CC=C(OC)C=C1 WTPPJTBHISKRRV-UHFFFAOYSA-N 0.000 claims 1
- YIYFEFGMARTRTD-UHFFFAOYSA-N ethyl 5-(dimethylcarbamoyl)-3,4-bis(dimethylcarbamoyloxy)-1-(4-methoxyphenyl)pyrrole-2-carboxylate Chemical compound CCOC(=O)C1=C(OC(=O)N(C)C)C(OC(=O)N(C)C)=C(C(=O)N(C)C)N1C1=CC=C(OC)C=C1 YIYFEFGMARTRTD-UHFFFAOYSA-N 0.000 claims 1
- UBNUVMDEYUQRDW-UHFFFAOYSA-N ethyl 5-(dimethylcarbamoyl)-3,4-bis[[2,2-dimethyl-3-(3-phosphonooxypropoxy)propanoyl]oxy]-1-(4-methoxyphenyl)pyrrole-2-carboxylate Chemical compound CC(C(=O)OC1=C(N(C(=C1OC(C(COCCCOP(=O)(O)O)(C)C)=O)C(=O)OCC)C1=CC=C(C=C1)OC)C(N(C)C)=O)(COCCCOP(=O)(O)O)C UBNUVMDEYUQRDW-UHFFFAOYSA-N 0.000 claims 1
- FDRUWMHNOCQLSN-UHFFFAOYSA-N ethyl 5-(dimethylcarbamoyl)-3,4-dihydroxy-1-(3-iodo-4-methoxyphenyl)pyrrole-2-carboxylate Chemical compound CCOC(=O)C1=C(O)C(O)=C(C(=O)N(C)C)N1C1=CC=C(OC)C(I)=C1 FDRUWMHNOCQLSN-UHFFFAOYSA-N 0.000 claims 1
- SXTHRUMZWXQKSI-UHFFFAOYSA-N ethyl 5-(dimethylcarbamoyl)-3,4-dihydroxy-1-(4-hydroxyphenyl)pyrrole-2-carboxylate Chemical compound CCOC(=O)C1=C(O)C(O)=C(C(=O)N(C)C)N1C1=CC=C(O)C=C1 SXTHRUMZWXQKSI-UHFFFAOYSA-N 0.000 claims 1
- VVTRQWNRKFXCCB-UHFFFAOYSA-N ethyl 5-(dimethylcarbamoyl)-3,4-dihydroxy-1-(4-iodophenyl)pyrrole-2-carboxylate Chemical compound CCOC(=O)C1=C(O)C(O)=C(C(=O)N(C)C)N1C1=CC=C(I)C=C1 VVTRQWNRKFXCCB-UHFFFAOYSA-N 0.000 claims 1
- MOSAQCXHHZZOMF-UHFFFAOYSA-N ethyl 5-(dimethylcarbamoyl)-3,4-dihydroxy-1-(4-phosphonooxyphenyl)pyrrole-2-carboxylate Chemical compound CCOC(=O)c1c(O)c(O)c(C(=O)N(C)C)n1-c1ccc(OP(O)(O)=O)cc1 MOSAQCXHHZZOMF-UHFFFAOYSA-N 0.000 claims 1
- XDNMCQWHGILEGI-UHFFFAOYSA-N ethyl 5-(dimethylcarbamoyl)-3,4-dihydroxy-1-[4-(2-methoxyethoxy)phenyl]pyrrole-2-carboxylate Chemical compound CCOC(=O)c1c(O)c(O)c(C(=O)N(C)C)n1-c1ccc(OCCOC)cc1 XDNMCQWHGILEGI-UHFFFAOYSA-N 0.000 claims 1
- SYQUQBUMLAZDPR-UHFFFAOYSA-N ethyl 5-(dimethylcarbamoyl)-3,4-dihydroxy-1-[4-(3-methylsulfonylpropoxy)phenyl]pyrrole-2-carboxylate Chemical compound CCOC(=O)C1=C(O)C(O)=C(C(=O)N(C)C)N1C1=CC=C(OCCCS(C)(=O)=O)C=C1 SYQUQBUMLAZDPR-UHFFFAOYSA-N 0.000 claims 1
- KAPYLRABHREAJJ-UHFFFAOYSA-N ethyl 5-(dimethylcarbamoyl)-3,4-dihydroxy-1-[4-(3-morpholin-4-ylpropoxy)phenyl]pyrrole-2-carboxylate Chemical compound CCOC(=O)C1=C(O)C(O)=C(C(=O)N(C)C)N1C(C=C1)=CC=C1OCCCN1CCOCC1 KAPYLRABHREAJJ-UHFFFAOYSA-N 0.000 claims 1
- XIOXEIHKKDYPFP-UHFFFAOYSA-N ethyl 5-(dimethylcarbamoyl)-3,4-dihydroxy-1-[4-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]phenyl]pyrrole-2-carboxylate Chemical compound CCOC(=O)c1c(O)c(O)c(C(=O)N(C)C)n1-c1ccc(OCCOCCOCCOCCOC)cc1 XIOXEIHKKDYPFP-UHFFFAOYSA-N 0.000 claims 1
- ZYKOLZDCPSZCFS-UHFFFAOYSA-N ethyl 5-(dimethylcarbamoyl)-3,4-dihydroxy-1-[4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]pyrrole-2-carboxylate Chemical compound CCOC(=O)c1c(O)c(O)c(C(=O)N(C)C)n1-c1ccc(OCCCN2CCN(C)CC2)cc1 ZYKOLZDCPSZCFS-UHFFFAOYSA-N 0.000 claims 1
- KXXHOAMJQSAVMQ-UHFFFAOYSA-N ethyl 5-(dimethylcarbamoyl)-3-hydroxy-1-(4-methoxyphenyl)-4-(phosphonooxymethoxy)pyrrole-2-carboxylate Chemical compound CCOC(=O)C1=C(O)C(OCOP(O)(O)=O)=C(C(=O)N(C)C)N1C1=CC=C(OC)C=C1 KXXHOAMJQSAVMQ-UHFFFAOYSA-N 0.000 claims 1
- INZHJFDYYHFGFH-UHFFFAOYSA-N ethyl 5-(dimethylcarbamoyl)-3-hydroxy-1-(4-methoxyphenyl)-4-phosphonooxypyrrole-2-carboxylate Chemical compound CCOC(=O)C1=C(O)C(OP(O)(O)=O)=C(C(=O)N(C)C)N1C1=CC=C(OC)C=C1 INZHJFDYYHFGFH-UHFFFAOYSA-N 0.000 claims 1
- BUDGCJRRYHDWOU-UHFFFAOYSA-N ethyl 5-(dimethylcarbamoyl)-3-hydroxy-1-(4-methoxyphenyl)-4-sulfamoyloxypyrrole-2-carboxylate Chemical compound CCOC(=O)C1=C(O)C(OS(N)(=O)=O)=C(C(=O)N(C)C)N1C1=CC=C(OC)C=C1 BUDGCJRRYHDWOU-UHFFFAOYSA-N 0.000 claims 1
- QDUHUECQPWUOSR-UHFFFAOYSA-N ethyl 5-(dimethylcarbamoyl)-4-(dimethylcarbamoyloxy)-3-hydroxy-1-(4-methoxyphenyl)pyrrole-2-carboxylate Chemical compound CCOC(=O)C1=C(O)C(OC(=O)N(C)C)=C(C(=O)N(C)C)N1C1=CC=C(OC)C=C1 QDUHUECQPWUOSR-UHFFFAOYSA-N 0.000 claims 1
- ZAJQHLQGSJYLOQ-UHFFFAOYSA-N ethyl 5-(dimethylcarbamoyl)-4-hydroxy-1-(4-methoxyphenyl)-3-(phosphonooxymethoxy)pyrrole-2-carboxylate Chemical compound CCOC(=O)C1=C(OCOP(O)(O)=O)C(O)=C(C(=O)N(C)C)N1C1=CC=C(OC)C=C1 ZAJQHLQGSJYLOQ-UHFFFAOYSA-N 0.000 claims 1
- FUJUFBVUSIOUKZ-UHFFFAOYSA-N ethyl 5-carbamoyl-1-(4-methoxyphenyl)-3,4-bis(phenylmethoxy)pyrrole-2-carboxylate Chemical compound C=1C=CC=CC=1COC1=C(C(N)=O)N(C=2C=CC(OC)=CC=2)C(C(=O)OCC)=C1OCC1=CC=CC=C1 FUJUFBVUSIOUKZ-UHFFFAOYSA-N 0.000 claims 1
- KFQKIYLCAGDAIB-UHFFFAOYSA-N ethyl 5-carbamoyl-3,4-dihydroxy-1-(4-methoxyphenyl)pyrrole-2-carboxylate Chemical compound CCOC(=O)C1=C(O)C(O)=C(C(N)=O)N1C1=CC=C(OC)C=C1 KFQKIYLCAGDAIB-UHFFFAOYSA-N 0.000 claims 1
- FKQFUBBNLJKLAX-UHFFFAOYSA-N ethyl 5-cyano-1-(4-fluorophenyl)-3,4-bis(phenylmethoxy)pyrrole-2-carboxylate Chemical compound C=1C=CC=CC=1COC1=C(C#N)N(C=2C=CC(F)=CC=2)C(C(=O)OCC)=C1OCC1=CC=CC=C1 FKQFUBBNLJKLAX-UHFFFAOYSA-N 0.000 claims 1
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| EP11191986.6A EP2602248A1 (en) | 2011-12-05 | 2011-12-05 | Novel pyrrole compounds |
| EP11191986.6 | 2011-12-05 | ||
| PCT/GB2012/053022 WO2013083975A2 (en) | 2011-12-05 | 2012-12-05 | Novel pyrrole derivatives |
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| IL (1) | IL232502A0 (enExample) |
| MX (1) | MX2014006686A (enExample) |
| SG (1) | SG11201402097XA (enExample) |
| WO (1) | WO2013083975A2 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2602248A1 (en) | 2011-12-05 | 2013-06-12 | University Of Leicester | Novel pyrrole compounds |
| GB201309935D0 (en) * | 2013-06-04 | 2013-07-17 | Univ Leicester | Novel pyrrole derivatives |
| GB201309932D0 (en) * | 2013-06-04 | 2013-07-17 | Univ Leicester | Novel pyrrole derivative |
| GB201309934D0 (en) * | 2013-06-04 | 2013-07-17 | Univ Leicester | Novel pyrrole derivatives |
| GB201309960D0 (en) * | 2013-06-04 | 2013-07-17 | Univ Leicester | Novel pyrrole derivatives |
| GB201310126D0 (en) * | 2013-06-06 | 2013-07-24 | Univ Leicester | Novel pyrrole derivatives |
| CN108129476A (zh) * | 2017-11-27 | 2018-06-08 | 华中农业大学 | 一种杂环内酰胺衍生物及其用于作物病原菌杀菌剂的用途 |
| GB201905721D0 (en) | 2019-04-24 | 2019-06-05 | Univ Dundee | Compounds |
| CN114736201B (zh) * | 2022-06-13 | 2022-09-02 | 奥锐特药业(天津)有限公司 | 芜地溴铵中间体的制备方法 |
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-
2011
- 2011-12-05 EP EP11191986.6A patent/EP2602248A1/en not_active Ceased
-
2012
- 2012-12-05 US US14/360,365 patent/US9221756B2/en not_active Expired - Fee Related
- 2012-12-05 SG SG11201402097XA patent/SG11201402097XA/en unknown
- 2012-12-05 WO PCT/GB2012/053022 patent/WO2013083975A2/en not_active Ceased
- 2012-12-05 CN CN201280060023.0A patent/CN104011019B/zh not_active Expired - Fee Related
- 2012-12-05 MX MX2014006686A patent/MX2014006686A/es unknown
- 2012-12-05 EP EP12830899.6A patent/EP2788324A2/en not_active Withdrawn
- 2012-12-05 HK HK15102414.7A patent/HK1201836A1/xx unknown
- 2012-12-05 AU AU2012349829A patent/AU2012349829A1/en not_active Abandoned
- 2012-12-05 CA CA2855351A patent/CA2855351A1/en not_active Abandoned
- 2012-12-05 JP JP2014545346A patent/JP2015500824A/ja active Pending
- 2012-12-05 BR BR112014012983A patent/BR112014012983A2/pt not_active IP Right Cessation
-
2014
- 2014-05-08 IL IL232502A patent/IL232502A0/en unknown
-
2015
- 2015-10-30 US US14/928,461 patent/US20160046576A1/en not_active Abandoned
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