JP2008510017A5 - - Google Patents
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- JP2008510017A5 JP2008510017A5 JP2007527928A JP2007527928A JP2008510017A5 JP 2008510017 A5 JP2008510017 A5 JP 2008510017A5 JP 2007527928 A JP2007527928 A JP 2007527928A JP 2007527928 A JP2007527928 A JP 2007527928A JP 2008510017 A5 JP2008510017 A5 JP 2008510017A5
- Authority
- JP
- Japan
- Prior art keywords
- phenylsulfanyl
- indole
- carboxylic acid
- acid amide
- methyl
- 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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- 150000001875 compounds Chemical class 0.000 claims 28
- 125000000623 heterocyclic group Chemical group 0.000 claims 13
- 125000003118 aryl group Chemical group 0.000 claims 9
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 7
- 229910052799 carbon Inorganic materials 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- -1 His Chemical compound 0.000 claims 6
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- JLYRSHVVQADSID-UHFFFAOYSA-N 3-phenylsulfanyl-5-(propylaminomethyl)-1h-indole-2-carboxamide Chemical compound C12=CC(CNCCC)=CC=C2NC(C(N)=O)=C1SC1=CC=CC=C1 JLYRSHVVQADSID-UHFFFAOYSA-N 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- HDHLISZWASJGHT-UHFFFAOYSA-N 1-[(2-bicyclo[2.2.1]heptanylamino)methyl]-3-phenylsulfanylindole-2-carboxamide Chemical compound C12=CC=CC=C2N(CNC2C3CCC(C3)C2)C(C(=O)N)=C1SC1=CC=CC=C1 HDHLISZWASJGHT-UHFFFAOYSA-N 0.000 claims 1
- ZRUUVAXNJWUIJO-UHFFFAOYSA-N 1-methyl-5-(methylaminomethyl)-3-phenylsulfanylindole-2-carboxamide Chemical compound C12=CC(CNC)=CC=C2N(C)C(C(N)=O)=C1SC1=CC=CC=C1 ZRUUVAXNJWUIJO-UHFFFAOYSA-N 0.000 claims 1
- 125000006325 2-propenyl amino group Chemical group [H]C([H])=C([H])C([H])([H])N([H])* 0.000 claims 1
- PHTVYNGDFBACTF-UHFFFAOYSA-N 3-(3-chlorophenyl)sulfanyl-5-(methylaminomethyl)-1h-indole-2-carboxamide Chemical compound C12=CC(CNC)=CC=C2NC(C(N)=O)=C1SC1=CC=CC(Cl)=C1 PHTVYNGDFBACTF-UHFFFAOYSA-N 0.000 claims 1
- OJFWSLXLAIEZSO-UHFFFAOYSA-N 3-(3-fluorophenyl)sulfanyl-5-(methylaminomethyl)-1h-indole-2-carboxamide Chemical compound C12=CC(CNC)=CC=C2NC(C(N)=O)=C1SC1=CC=CC(F)=C1 OJFWSLXLAIEZSO-UHFFFAOYSA-N 0.000 claims 1
- KSZFGVPYJPGQDB-UHFFFAOYSA-N 3-amino-4-[(2-carbamoyl-3-phenylsulfanyl-1h-indol-6-yl)methylamino]-4-oxobutanoic acid Chemical compound NC(=O)C=1NC2=CC(CNC(=O)C(CC(O)=O)N)=CC=C2C=1SC1=CC=CC=C1 KSZFGVPYJPGQDB-UHFFFAOYSA-N 0.000 claims 1
- BXJWUHNROITKOB-UHFFFAOYSA-N 3-phenylsulfanyl-5-(piperidin-1-ylmethyl)-1h-indole-2-carboxamide Chemical compound C1=C2C(SC=3C=CC=CC=3)=C(C(=O)N)NC2=CC=C1CN1CCCCC1 BXJWUHNROITKOB-UHFFFAOYSA-N 0.000 claims 1
- YUDYVWVBVNISFO-UHFFFAOYSA-N 3-phenylsulfanyl-5-[(4-pyrimidin-2-ylpiperazin-1-yl)methyl]-1h-indole-2-carboxamide Chemical compound C1=C2C(SC=3C=CC=CC=3)=C(C(=O)N)NC2=CC=C1CN(CC1)CCN1C1=NC=CC=N1 YUDYVWVBVNISFO-UHFFFAOYSA-N 0.000 claims 1
- JUQZGNJVJIHARC-UHFFFAOYSA-N 3-phenylsulfanyl-5-[(propan-2-ylamino)methyl]-1h-indole-2-carboxamide Chemical compound C12=CC(CNC(C)C)=CC=C2NC(C(N)=O)=C1SC1=CC=CC=C1 JUQZGNJVJIHARC-UHFFFAOYSA-N 0.000 claims 1
- PQWRIVOWPXRRJX-UHFFFAOYSA-N 3-phenylsulfanyl-5-[(quinolin-6-ylamino)methyl]-1h-indole-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=C(CNC=3C=C4C=CC=NC4=CC=3)C=C2C=1SC1=CC=CC=C1 PQWRIVOWPXRRJX-UHFFFAOYSA-N 0.000 claims 1
- LRKWJJYDPQPEEQ-UHFFFAOYSA-N 3-phenylsulfanyl-5-[[3-(trifluoromethyl)anilino]methyl]-1h-indole-2-carboxamide Chemical compound C1=C2C(SC=3C=CC=CC=3)=C(C(=O)N)NC2=CC=C1CNC1=CC=CC(C(F)(F)F)=C1 LRKWJJYDPQPEEQ-UHFFFAOYSA-N 0.000 claims 1
- ZVSMVUSAVZIXCE-UHFFFAOYSA-N 3-phenylsulfanyl-6-[[[4-(trifluoromethyl)phenyl]methylamino]methyl]-1h-indole-2-carboxamide Chemical compound C=1C=C2C(SC=3C=CC=CC=3)=C(C(=O)N)NC2=CC=1CNCC1=CC=C(C(F)(F)F)C=C1 ZVSMVUSAVZIXCE-UHFFFAOYSA-N 0.000 claims 1
- SHKMPRXGCZCJQL-UHFFFAOYSA-N 5-(1,4-diazepan-1-ylmethyl)-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C1=C2C(SC=3C=CC=CC=3)=C(C(=O)N)NC2=CC=C1CN1CCCNCC1 SHKMPRXGCZCJQL-UHFFFAOYSA-N 0.000 claims 1
- SYZDABMIUZMPPL-UHFFFAOYSA-N 5-(1,4-dioxa-8-azaspiro[4.5]decan-8-ylmethyl)-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C1=C2C(SC=3C=CC=CC=3)=C(C(=O)N)NC2=CC=C1CN(CC1)CCC21OCCO2 SYZDABMIUZMPPL-UHFFFAOYSA-N 0.000 claims 1
- ZRSYJRIKLSTZMT-UHFFFAOYSA-N 5-(aminomethyl)-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C12=CC(CN)=CC=C2NC(C(N)=O)=C1SC1=CC=CC=C1 ZRSYJRIKLSTZMT-UHFFFAOYSA-N 0.000 claims 1
- UDUXBKHRALVKNO-UHFFFAOYSA-N 5-(butylaminomethyl)-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C12=CC(CNCCCC)=CC=C2NC(C(N)=O)=C1SC1=CC=CC=C1 UDUXBKHRALVKNO-UHFFFAOYSA-N 0.000 claims 1
- HLZRKWABRSXWTB-UHFFFAOYSA-N 5-(ethylaminomethyl)-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C12=CC(CNCC)=CC=C2NC(C(N)=O)=C1SC1=CC=CC=C1 HLZRKWABRSXWTB-UHFFFAOYSA-N 0.000 claims 1
- TZYCYPZBYDYRQB-UHFFFAOYSA-N 5-(methylaminomethyl)-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C12=CC(CNC)=CC=C2NC(C(N)=O)=C1SC1=CC=CC=C1 TZYCYPZBYDYRQB-UHFFFAOYSA-N 0.000 claims 1
- XLAUWVOGJHPJML-UHFFFAOYSA-N 5-(morpholin-4-ylmethyl)-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C1=C2C(SC=3C=CC=CC=3)=C(C(=O)N)NC2=CC=C1CN1CCOCC1 XLAUWVOGJHPJML-UHFFFAOYSA-N 0.000 claims 1
- VIQIAMCXYSBYQY-UHFFFAOYSA-N 5-[(1-hydroxypropan-2-ylamino)methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C12=CC(CNC(CO)C)=CC=C2NC(C(N)=O)=C1SC1=CC=CC=C1 VIQIAMCXYSBYQY-UHFFFAOYSA-N 0.000 claims 1
- RYWSGPKTJTWPJH-UHFFFAOYSA-N 5-[(2,3-dihydroxypropylamino)methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=C(CNCC(O)CO)C=C2C=1SC1=CC=CC=C1 RYWSGPKTJTWPJH-UHFFFAOYSA-N 0.000 claims 1
- LCFUECWRWISTPP-UHFFFAOYSA-N 5-[(2-cyano-4,5-dimethoxyanilino)methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C1=C(OC)C(OC)=CC(NCC=2C=C3C(SC=4C=CC=CC=4)=C(C(N)=O)NC3=CC=2)=C1C#N LCFUECWRWISTPP-UHFFFAOYSA-N 0.000 claims 1
- WWFKUELLAFXIEG-UHFFFAOYSA-N 5-[(2-fluoroanilino)methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C1=C2C(SC=3C=CC=CC=3)=C(C(=O)N)NC2=CC=C1CNC1=CC=CC=C1F WWFKUELLAFXIEG-UHFFFAOYSA-N 0.000 claims 1
- LARCNPWNXCRVKY-UHFFFAOYSA-N 5-[(3-carbamoylpiperidin-1-yl)methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C1C(C(=O)N)CCCN1CC1=CC=C(NC(C(N)=O)=C2SC=3C=CC=CC=3)C2=C1 LARCNPWNXCRVKY-UHFFFAOYSA-N 0.000 claims 1
- WVKHZVHKRFIYHU-UHFFFAOYSA-N 5-[(3-methoxyanilino)methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound COC1=CC=CC(NCC=2C=C3C(SC=4C=CC=CC=4)=C(C(N)=O)NC3=CC=2)=C1 WVKHZVHKRFIYHU-UHFFFAOYSA-N 0.000 claims 1
- VRUDQDCPQOQGDE-UHFFFAOYSA-N 5-[(4-butylanilino)methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C1=CC(CCCC)=CC=C1NCC1=CC=C(NC(C(N)=O)=C2SC=3C=CC=CC=3)C2=C1 VRUDQDCPQOQGDE-UHFFFAOYSA-N 0.000 claims 1
- IPEWRCABZMBLLR-UHFFFAOYSA-N 5-[(benzylamino)methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C1=C2C(SC=3C=CC=CC=3)=C(C(=O)N)NC2=CC=C1CNCC1=CC=CC=C1 IPEWRCABZMBLLR-UHFFFAOYSA-N 0.000 claims 1
- DAAPUDXKYYZXKS-UHFFFAOYSA-N 5-[(heptylamino)methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C12=CC(CNCCCCCCC)=CC=C2NC(C(N)=O)=C1SC1=CC=CC=C1 DAAPUDXKYYZXKS-UHFFFAOYSA-N 0.000 claims 1
- OCICEAWBXNDPAL-UHFFFAOYSA-N 5-[(pentylamino)methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C12=CC(CNCCCCC)=CC=C2NC(C(N)=O)=C1SC1=CC=CC=C1 OCICEAWBXNDPAL-UHFFFAOYSA-N 0.000 claims 1
- BBVKPLPOVHBJGO-UHFFFAOYSA-N 5-[[(1,3-dihydroxy-2-methylpropan-2-yl)amino]methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C12=CC(CNC(CO)(CO)C)=CC=C2NC(C(N)=O)=C1SC1=CC=CC=C1 BBVKPLPOVHBJGO-UHFFFAOYSA-N 0.000 claims 1
- CCUHUKCNAKYYIH-UHFFFAOYSA-N 5-[[(1-amino-1-oxopropan-2-yl)amino]methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C12=CC(CNC(C)C(N)=O)=CC=C2NC(C(N)=O)=C1SC1=CC=CC=C1 CCUHUKCNAKYYIH-UHFFFAOYSA-N 0.000 claims 1
- BSOFVACFRCOLPE-UHFFFAOYSA-N 5-[[2-(hydroxymethyl)pyrrolidin-1-yl]methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C1=C2C(SC=3C=CC=CC=3)=C(C(=O)N)NC2=CC=C1CN1CCCC1CO BSOFVACFRCOLPE-UHFFFAOYSA-N 0.000 claims 1
- BKPVPPGKGHXIJE-UHFFFAOYSA-N 5-[[4-(3-phenylprop-1-enyl)piperazin-1-yl]methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C1=C2C(SC=3C=CC=CC=3)=C(C(=O)N)NC2=CC=C1CN(CC1)CCN1C=CCC1=CC=CC=C1 BKPVPPGKGHXIJE-UHFFFAOYSA-N 0.000 claims 1
- CWKFMXVKGKBRJP-UHFFFAOYSA-N 5-[[4-(4-fluorophenyl)piperazin-1-yl]methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C1=C2C(SC=3C=CC=CC=3)=C(C(=O)N)NC2=CC=C1CN(CC1)CCN1C1=CC=C(F)C=C1 CWKFMXVKGKBRJP-UHFFFAOYSA-N 0.000 claims 1
- ROEZJVSADVPLTJ-UHFFFAOYSA-N 5-[[4-(hydroxymethyl)piperidin-1-yl]methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C1=C2C(SC=3C=CC=CC=3)=C(C(=O)N)NC2=CC=C1CN1CCC(CO)CC1 ROEZJVSADVPLTJ-UHFFFAOYSA-N 0.000 claims 1
- GKLVGVOVOMDNTG-UHFFFAOYSA-N 6-(aminomethyl)-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound NC(=O)C=1NC2=CC(CN)=CC=C2C=1SC1=CC=CC=C1 GKLVGVOVOMDNTG-UHFFFAOYSA-N 0.000 claims 1
- NLWLOSBVSVYELF-UHFFFAOYSA-N 6-[(2,6-diaminohexanoylamino)methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound NC(=O)C=1NC2=CC(CNC(=O)C(N)CCCCN)=CC=C2C=1SC1=CC=CC=C1 NLWLOSBVSVYELF-UHFFFAOYSA-N 0.000 claims 1
- LUMOFRIFMDHOOY-UHFFFAOYSA-N 6-[(2-aminopropanoylamino)methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound NC(=O)C=1NC2=CC(CNC(=O)C(N)C)=CC=C2C=1SC1=CC=CC=C1 LUMOFRIFMDHOOY-UHFFFAOYSA-N 0.000 claims 1
- FPICROACQHOCMQ-UHFFFAOYSA-N 6-[(benzylamino)methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C=1C=C2C(SC=3C=CC=CC=3)=C(C(=O)N)NC2=CC=1CNCC1=CC=CC=C1 FPICROACQHOCMQ-UHFFFAOYSA-N 0.000 claims 1
- SVXRHJHEGAVNQY-UHFFFAOYSA-N 6-[[(10-chloroanthracen-9-yl)methylamino]methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound NC(=O)C=1NC2=CC(CNCC=3C4=CC=CC=C4C(Cl)=C4C=CC=CC4=3)=CC=C2C=1SC1=CC=CC=C1 SVXRHJHEGAVNQY-UHFFFAOYSA-N 0.000 claims 1
- QBFFUIRRVWFQGF-UHFFFAOYSA-N 6-[[(2,4-dimethoxyphenyl)methylamino]methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound COC1=CC(OC)=CC=C1CNCC1=CC=C(C(SC=2C=CC=CC=2)=C(N2)C(N)=O)C2=C1 QBFFUIRRVWFQGF-UHFFFAOYSA-N 0.000 claims 1
- RREKJZCVYBLDDA-UHFFFAOYSA-N 6-[[(2-amino-3-methylpentanoyl)amino]methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound NC(=O)C=1NC2=CC(CNC(=O)C(N)C(C)CC)=CC=C2C=1SC1=CC=CC=C1 RREKJZCVYBLDDA-UHFFFAOYSA-N 0.000 claims 1
- WEQYXTUOZWXXHA-UHFFFAOYSA-N 6-[[(2-amino-3-phenylpropanoyl)amino]methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C=1C=C2C(SC=3C=CC=CC=3)=C(C(N)=O)NC2=CC=1CNC(=O)C(N)CC1=CC=CC=C1 WEQYXTUOZWXXHA-UHFFFAOYSA-N 0.000 claims 1
- MYTUDELNCGATRF-UHFFFAOYSA-N 6-[[(2-amino-4-methylsulfanylbutanoyl)amino]methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound NC(=O)C=1NC2=CC(CNC(=O)C(N)CCSC)=CC=C2C=1SC1=CC=CC=C1 MYTUDELNCGATRF-UHFFFAOYSA-N 0.000 claims 1
- AAECZAPATSJXKY-UHFFFAOYSA-N 6-[[(2-aminoacetyl)amino]methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound NC(=O)C=1NC2=CC(CNC(=O)CN)=CC=C2C=1SC1=CC=CC=C1 AAECZAPATSJXKY-UHFFFAOYSA-N 0.000 claims 1
- NNXGDKGCTQFQHZ-UHFFFAOYSA-N 6-[[(2-methoxyphenyl)methylamino]methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound COC1=CC=CC=C1CNCC1=CC=C(C(SC=2C=CC=CC=2)=C(N2)C(N)=O)C2=C1 NNXGDKGCTQFQHZ-UHFFFAOYSA-N 0.000 claims 1
- SJZNOQDCSSUVCX-UHFFFAOYSA-N 6-[[(2-methylphenyl)methylamino]methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound CC1=CC=CC=C1CNCC1=CC=C(C(SC=2C=CC=CC=2)=C(N2)C(N)=O)C2=C1 SJZNOQDCSSUVCX-UHFFFAOYSA-N 0.000 claims 1
- WHRSOILXCZNCPE-UHFFFAOYSA-N 6-[[(2-nitrophenyl)methylamino]methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C=1C=C2C(SC=3C=CC=CC=3)=C(C(=O)N)NC2=CC=1CNCC1=CC=CC=C1[N+]([O-])=O WHRSOILXCZNCPE-UHFFFAOYSA-N 0.000 claims 1
- MKIJAGJRNHRXFV-UHFFFAOYSA-N 6-[[(3,5-dichloro-2-hydroxyphenyl)methylamino]methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C=1C=C2C(SC=3C=CC=CC=3)=C(C(=O)N)NC2=CC=1CNCC1=CC(Cl)=CC(Cl)=C1O MKIJAGJRNHRXFV-UHFFFAOYSA-N 0.000 claims 1
- JNBRXRYABBEGOU-UHFFFAOYSA-N 6-[[(3-bromo-4,5-dimethoxyphenyl)methylamino]methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound BrC1=C(OC)C(OC)=CC(CNCC=2C=C3NC(=C(SC=4C=CC=CC=4)C3=CC=2)C(N)=O)=C1 JNBRXRYABBEGOU-UHFFFAOYSA-N 0.000 claims 1
- GESOVJVFJICPLO-UHFFFAOYSA-N 6-[[(3-methoxy-4-phenylmethoxyphenyl)methylamino]methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C=1C=C(OCC=2C=CC=CC=2)C(OC)=CC=1CNCC(C=C1NC=2C(N)=O)=CC=C1C=2SC1=CC=CC=C1 GESOVJVFJICPLO-UHFFFAOYSA-N 0.000 claims 1
- VUJXYLNLAYONKC-UHFFFAOYSA-N 6-[[(3-methoxyphenyl)methylamino]methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound COC1=CC=CC(CNCC=2C=C3NC(=C(SC=4C=CC=CC=4)C3=CC=2)C(N)=O)=C1 VUJXYLNLAYONKC-UHFFFAOYSA-N 0.000 claims 1
- AZIFEVBGESSHHF-UHFFFAOYSA-N 6-[[(3-methylphenyl)methylamino]methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound CC1=CC=CC(CNCC=2C=C3NC(=C(SC=4C=CC=CC=4)C3=CC=2)C(N)=O)=C1 AZIFEVBGESSHHF-UHFFFAOYSA-N 0.000 claims 1
- FSAMQLVJXSLOHX-UHFFFAOYSA-N 6-[[(3-nitrophenyl)methylamino]methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C=1C=C2C(SC=3C=CC=CC=3)=C(C(=O)N)NC2=CC=1CNCC1=CC=CC([N+]([O-])=O)=C1 FSAMQLVJXSLOHX-UHFFFAOYSA-N 0.000 claims 1
- MQJFHCOOJOGQCM-UHFFFAOYSA-N 6-[[(3-phenoxyphenyl)methylamino]methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C=1C=C2C(SC=3C=CC=CC=3)=C(C(=O)N)NC2=CC=1CNCC(C=1)=CC=CC=1OC1=CC=CC=C1 MQJFHCOOJOGQCM-UHFFFAOYSA-N 0.000 claims 1
- SAJPAWRVFRDJJX-UHFFFAOYSA-N 6-[[(4-bromophenyl)methylamino]methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C=1C=C2C(SC=3C=CC=CC=3)=C(C(=O)N)NC2=CC=1CNCC1=CC=C(Br)C=C1 SAJPAWRVFRDJJX-UHFFFAOYSA-N 0.000 claims 1
- LKBQWPLEIQKZIG-UHFFFAOYSA-N 6-[[(4-chlorophenyl)methylamino]methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C=1C=C2C(SC=3C=CC=CC=3)=C(C(=O)N)NC2=CC=1CNCC1=CC=C(Cl)C=C1 LKBQWPLEIQKZIG-UHFFFAOYSA-N 0.000 claims 1
- NKYALTYFEFDZFM-UHFFFAOYSA-N 6-[[(4-methoxy-3-phenylmethoxyphenyl)methylamino]methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C1=C(OCC=2C=CC=CC=2)C(OC)=CC=C1CNCC(C=C1NC=2C(N)=O)=CC=C1C=2SC1=CC=CC=C1 NKYALTYFEFDZFM-UHFFFAOYSA-N 0.000 claims 1
- RIUGQEZGFSVYQB-UHFFFAOYSA-N 6-[[(4-methoxyphenyl)methylamino]methyl]-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound C1=CC(OC)=CC=C1CNCC1=CC=C(C(SC=2C=CC=CC=2)=C(N2)C(N)=O)C2=C1 RIUGQEZGFSVYQB-UHFFFAOYSA-N 0.000 claims 1
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| JP4748823B2 (ja) * | 2009-02-12 | 2011-08-17 | 株式会社ファルマデザイン | カゼインキナーゼ１δ及びカゼインキナーゼ１ε阻害剤 |
| SG175210A1 (en) * | 2009-04-17 | 2011-11-28 | Cylene Pharmaceuticals Inc | Method of treating disorders associated with protein kinase ck2 activity |
| CA2877589C (en) | 2012-06-27 | 2019-11-26 | 4Sc Ag | Bifluorodioxalane-amino-benzimidazole kinase inhibitors for the treatment of cancer, autoimmuneinflammation and cns disorders |
| JP2021511364A (ja) | 2018-01-29 | 2021-05-06 | カディラ ヘルスケア リミティド | 抗菌剤として有用な複素環式化合物 |
| WO2022006377A2 (en) | 2020-07-02 | 2022-01-06 | Mbq Pharma | Heterocyclic inhibitors of rho gtpases for the treatment of disease |
| US12209078B2 (en) | 2021-10-06 | 2025-01-28 | Mbq Pharma | Crystalline forms of carbazole inhibitors of RhoGTPase for the treatment of disease |
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| US5296471A (en) | 1992-12-22 | 1994-03-22 | Glycomed Incorporated | Method for controlling o-desulfation of heparin and compositions produced thereby |
| KR100722176B1 (ko) | 1999-06-08 | 2007-05-29 | 아벤티스 파마슈티칼스 인크. | 일주기 리듬 단백질을 변화시키기 위한 스크리닝 방법 |
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| CA2494962C (en) * | 2002-08-09 | 2011-06-14 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
| CN100439367C (zh) * | 2003-12-11 | 2008-12-03 | 安万特药物公司 | 作为酪蛋白激酶Iε抑制剂的取代的1H-吡咯并[3,2-b、3,2-c和2,3-c]吡啶-2-甲酰胺以及相关类似物 |
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2005
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2007
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2008
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