JP2011513196A - ドーパミン作動系が破壊された障害もしくは状態の症状を軽減するためまたはその障害もしくは状態を処置するためのkcnqカリウムチャネル開口薬の使用 - Google Patents
ドーパミン作動系が破壊された障害もしくは状態の症状を軽減するためまたはその障害もしくは状態を処置するためのkcnqカリウムチャネル開口薬の使用 Download PDFInfo
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- JP2011513196A JP2011513196A JP2010518498A JP2010518498A JP2011513196A JP 2011513196 A JP2011513196 A JP 2011513196A JP 2010518498 A JP2010518498 A JP 2010518498A JP 2010518498 A JP2010518498 A JP 2010518498A JP 2011513196 A JP2011513196 A JP 2011513196A
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- Prior art keywords
- phenyl
- keni
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- methyl
- alk
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- UYUQLIZCUOSRRQ-UHFFFAOYSA-N 2-methoxyethyl n-[2,6-dimethyl-4-[[4-(trifluoromethyl)anilino]methyl]phenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCCOC)=C(C)C=C1CNC1=CC=C(C(F)(F)F)C=C1 UYUQLIZCUOSRRQ-UHFFFAOYSA-N 0.000 claims description 2
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- SJAIYFDQCITQLJ-UHFFFAOYSA-N 3-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]-1-methyl-1-propylurea Chemical compound C1=C(Cl)C(NC(=O)N(C)CCC)=CC=C1N(C)CC1=CC=C(Cl)S1 SJAIYFDQCITQLJ-UHFFFAOYSA-N 0.000 claims description 2
- NKRSJPBJRWPWTO-UHFFFAOYSA-N 3-chloropropyl n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]carbamate Chemical compound C=1C=C(NC(=O)OCCCCl)C(Cl)=CC=1N(C)CC1=CC=C(Cl)S1 NKRSJPBJRWPWTO-UHFFFAOYSA-N 0.000 claims description 2
- PVKGAFIBJUZLPW-UHFFFAOYSA-N 3-cyclohexyl-n-(2,4-dimethyl-6-morpholin-4-ylpyridin-3-yl)propanamide Chemical compound CC1=CC(N2CCOCC2)=NC(C)=C1NC(=O)CCC1CCCCC1 PVKGAFIBJUZLPW-UHFFFAOYSA-N 0.000 claims description 2
- FFJSHGKHOFZMRC-UHFFFAOYSA-N 3-cyclohexyl-n-(2,6-dimethyl-4-morpholin-4-ylphenyl)propanamide Chemical compound CC1=CC(N2CCOCC2)=CC(C)=C1NC(=O)CCC1CCCCC1 FFJSHGKHOFZMRC-UHFFFAOYSA-N 0.000 claims description 2
- WHTGDXHISJRNKN-UHFFFAOYSA-N 3-cyclopentyl-n-(2,4-dimethyl-6-morpholin-4-ylpyridin-3-yl)propanamide Chemical compound CC1=CC(N2CCOCC2)=NC(C)=C1NC(=O)CCC1CCCC1 WHTGDXHISJRNKN-UHFFFAOYSA-N 0.000 claims description 2
- FQHLBMKMJMGTSG-UHFFFAOYSA-N 3-cyclopentyl-n-(2,6-dimethyl-4-morpholin-4-ylphenyl)propanamide Chemical compound CC1=CC(N2CCOCC2)=CC(C)=C1NC(=O)CCC1CCCC1 FQHLBMKMJMGTSG-UHFFFAOYSA-N 0.000 claims description 2
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- 125000001318 4-trifluoromethylbenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(F)(F)F 0.000 claims description 2
- OGABBSFCFIJRPK-UHFFFAOYSA-N 5-methyl-n-[2-methyl-4-morpholin-4-yl-6-(trifluoromethyl)phenyl]hexanamide Chemical compound C1=C(C(F)(F)F)C(NC(=O)CCCC(C)C)=C(C)C=C1N1CCOCC1 OGABBSFCFIJRPK-UHFFFAOYSA-N 0.000 claims description 2
- IAUIUXXKRXWWNW-UHFFFAOYSA-N COC1=CSC2=C1C=CC(=C2)Cl Chemical compound COC1=CSC2=C1C=CC(=C2)Cl IAUIUXXKRXWWNW-UHFFFAOYSA-N 0.000 claims description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 2
- 208000026139 Memory disease Diseases 0.000 claims description 2
- 208000013716 Motor tics Diseases 0.000 claims description 2
- 235000018936 Vitellaria paradoxa Nutrition 0.000 claims description 2
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 2
- KAEMILXLUFFLSU-UHFFFAOYSA-N benzyl n-(2,4-dimethyl-6-morpholin-4-ylpyridin-3-yl)carbamate Chemical compound CC1=CC(N2CCOCC2)=NC(C)=C1NC(=O)OCC1=CC=CC=C1 KAEMILXLUFFLSU-UHFFFAOYSA-N 0.000 claims description 2
- DDAWRADOFRFSCU-UHFFFAOYSA-N benzyl n-(2,6-dimethyl-4-morpholin-4-ylphenyl)carbamate Chemical compound CC1=CC(N2CCOCC2)=CC(C)=C1NC(=O)OCC1=CC=CC=C1 DDAWRADOFRFSCU-UHFFFAOYSA-N 0.000 claims description 2
- QIUJJJVRYWFJPB-UHFFFAOYSA-N benzyl n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]carbamate Chemical compound C=1C=C(NC(=O)OCC=2C=CC=CC=2)C(Cl)=CC=1N(C)CC1=CC=C(Cl)S1 QIUJJJVRYWFJPB-UHFFFAOYSA-N 0.000 claims description 2
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 claims description 2
- GFLUXUNNWRGAJS-UHFFFAOYSA-N but-2-ynyl n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]carbamate Chemical compound C1=C(Cl)C(NC(=O)OCC#CC)=CC=C1N(C)CC1=CC=C(Cl)S1 GFLUXUNNWRGAJS-UHFFFAOYSA-N 0.000 claims description 2
- NTCMMLFINXWYDI-UHFFFAOYSA-N but-3-enyl n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]carbamate Chemical compound C=1C=C(NC(=O)OCCC=C)C(Cl)=CC=1N(C)CC1=CC=C(Cl)S1 NTCMMLFINXWYDI-UHFFFAOYSA-N 0.000 claims description 2
- CSWQFUWZYDMBLR-UHFFFAOYSA-N butyl n-(2,6-dimethyl-4-morpholin-4-ylphenyl)carbamate Chemical compound C1=C(C)C(NC(=O)OCCCC)=C(C)C=C1N1CCOCC1 CSWQFUWZYDMBLR-UHFFFAOYSA-N 0.000 claims description 2
- RRBPKGFPYVBTPQ-UHFFFAOYSA-N butyl n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]carbamate Chemical compound C1=C(Cl)C(NC(=O)OCCCC)=CC=C1N(C)CC1=CC=C(Cl)S1 RRBPKGFPYVBTPQ-UHFFFAOYSA-N 0.000 claims description 2
- 230000003001 depressive effect Effects 0.000 claims description 2
- YYIFYTOIDVFSJM-UHFFFAOYSA-N ethyl n-(4-bromo-2,6-dimethylphenyl)carbamate Chemical compound CCOC(=O)NC1=C(C)C=C(Br)C=C1C YYIFYTOIDVFSJM-UHFFFAOYSA-N 0.000 claims description 2
- IECMFWSPQDIVPW-UHFFFAOYSA-N ethyl n-[2,6-dimethyl-4-[[4-(trifluoromethyl)anilino]methyl]phenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCC)=C(C)C=C1CNC1=CC=C(C(F)(F)F)C=C1 IECMFWSPQDIVPW-UHFFFAOYSA-N 0.000 claims description 2
- LVDKVOBNMQQEAL-UHFFFAOYSA-N ethyl n-[2-(4-chlorophenyl)-4-[(3-fluoroanilino)methyl]phenyl]carbamate Chemical compound C1=C(C=2C=CC(Cl)=CC=2)C(NC(=O)OCC)=CC=C1CNC1=CC=CC(F)=C1 LVDKVOBNMQQEAL-UHFFFAOYSA-N 0.000 claims description 2
- JBASQAITBFAGGZ-UHFFFAOYSA-N ethyl n-[2-(4-chlorophenyl)-4-[[4-(trifluoromethyl)anilino]methyl]phenyl]carbamate Chemical compound C1=C(C=2C=CC(Cl)=CC=2)C(NC(=O)OCC)=CC=C1CNC1=CC=C(C(F)(F)F)C=C1 JBASQAITBFAGGZ-UHFFFAOYSA-N 0.000 claims description 2
- AVLRKXVHQCYJLZ-UHFFFAOYSA-N ethyl n-[2-[4-(dimethylamino)phenyl]-4-[(3-fluoroanilino)methyl]phenyl]carbamate Chemical compound C1=C(C=2C=CC(=CC=2)N(C)C)C(NC(=O)OCC)=CC=C1CNC1=CC=CC(F)=C1 AVLRKXVHQCYJLZ-UHFFFAOYSA-N 0.000 claims description 2
- TYFOODIYYYOWKK-UHFFFAOYSA-N ethyl n-[2-[4-(dimethylamino)phenyl]-4-[[4-(trifluoromethyl)anilino]methyl]phenyl]carbamate Chemical compound C1=C(C=2C=CC(=CC=2)N(C)C)C(NC(=O)OCC)=CC=C1CNC1=CC=C(C(F)(F)F)C=C1 TYFOODIYYYOWKK-UHFFFAOYSA-N 0.000 claims description 2
- KXYHFTARJIQOMA-UHFFFAOYSA-N ethyl n-[2-amino-4-(1-benzothiophen-3-ylmethylamino)phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1NCC1=CSC2=CC=CC=C12 KXYHFTARJIQOMA-UHFFFAOYSA-N 0.000 claims description 2
- PAUMPFSSOXRDEJ-UHFFFAOYSA-N ethyl n-[2-amino-4-(anilinomethyl)phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1CNC1=CC=CC=C1 PAUMPFSSOXRDEJ-UHFFFAOYSA-N 0.000 claims description 2
- CYVMSJCKTMVSRR-UHFFFAOYSA-N ethyl n-[2-amino-4-(thiophen-2-ylmethylamino)phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1NCC1=CC=CS1 CYVMSJCKTMVSRR-UHFFFAOYSA-N 0.000 claims description 2
- WALRLVHHRQJWMT-UHFFFAOYSA-N ethyl n-[2-amino-4-(thiophen-3-ylmethylamino)phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1NCC1=CSC=C1 WALRLVHHRQJWMT-UHFFFAOYSA-N 0.000 claims description 2
- XFNGDUVFJSECBN-UHFFFAOYSA-N ethyl n-[2-amino-4-[(2,3-dichloroanilino)methyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1CNC1=CC=CC(Cl)=C1Cl XFNGDUVFJSECBN-UHFFFAOYSA-N 0.000 claims description 2
- NPFOVUKAFGUSQL-UHFFFAOYSA-N ethyl n-[2-amino-4-[(2,3-dihydro-1h-inden-5-ylamino)methyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1CNC1=CC=C(CCC2)C2=C1 NPFOVUKAFGUSQL-UHFFFAOYSA-N 0.000 claims description 2
- SCOOTUMXCXKEAD-UHFFFAOYSA-N ethyl n-[2-amino-4-[(2,4,6-trimethylphenyl)methylamino]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1NCC1=C(C)C=C(C)C=C1C SCOOTUMXCXKEAD-UHFFFAOYSA-N 0.000 claims description 2
- MPNLUKUAXMXGGU-UHFFFAOYSA-N ethyl n-[2-amino-4-[(2,4-dichloroanilino)methyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1CNC1=CC=C(Cl)C=C1Cl MPNLUKUAXMXGGU-UHFFFAOYSA-N 0.000 claims description 2
- XVKFYUITXXYYEN-UHFFFAOYSA-N ethyl n-[2-amino-4-[(2,4-difluoroanilino)methyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1CNC1=CC=C(F)C=C1F XVKFYUITXXYYEN-UHFFFAOYSA-N 0.000 claims description 2
- VDDRKSVFMCGVKS-UHFFFAOYSA-N ethyl n-[2-amino-4-[(2-fluoroanilino)methyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1CNC1=CC=CC=C1F VDDRKSVFMCGVKS-UHFFFAOYSA-N 0.000 claims description 2
- YCMRKXZMNUMKST-UHFFFAOYSA-N ethyl n-[2-amino-4-[(3,4-dichloroanilino)methyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1CNC1=CC=C(Cl)C(Cl)=C1 YCMRKXZMNUMKST-UHFFFAOYSA-N 0.000 claims description 2
- PJFKUBNCMZLCEL-UHFFFAOYSA-N ethyl n-[2-amino-4-[(3,4-difluoroanilino)methyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1CNC1=CC=C(F)C(F)=C1 PJFKUBNCMZLCEL-UHFFFAOYSA-N 0.000 claims description 2
- HFTMLRRJCMKHCO-UHFFFAOYSA-N ethyl n-[2-amino-4-[(3,5-dichloroanilino)methyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1CNC1=CC(Cl)=CC(Cl)=C1 HFTMLRRJCMKHCO-UHFFFAOYSA-N 0.000 claims description 2
- GXONDZRSDZSZRZ-UHFFFAOYSA-N ethyl n-[2-amino-4-[(3-chloro-4-methylanilino)methyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1CNC1=CC=C(C)C(Cl)=C1 GXONDZRSDZSZRZ-UHFFFAOYSA-N 0.000 claims description 2
- STCYUEYAARANPB-UHFFFAOYSA-N ethyl n-[2-amino-4-[(3-chloroanilino)methyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1CNC1=CC=CC(Cl)=C1 STCYUEYAARANPB-UHFFFAOYSA-N 0.000 claims description 2
- NGFUMNQGNPBYMN-UHFFFAOYSA-N ethyl n-[2-amino-4-[(3-chlorothiophen-2-yl)methylamino]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1NCC1=C(Cl)C=CS1 NGFUMNQGNPBYMN-UHFFFAOYSA-N 0.000 claims description 2
- RAVCWWJMYAMNLK-UHFFFAOYSA-N ethyl n-[2-amino-4-[(3-fluoroanilino)methyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1CNC1=CC=CC(F)=C1 RAVCWWJMYAMNLK-UHFFFAOYSA-N 0.000 claims description 2
- RNFBDOBYXLGUBY-UHFFFAOYSA-N ethyl n-[2-amino-4-[(3-methylanilino)methyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1CNC1=CC=CC(C)=C1 RNFBDOBYXLGUBY-UHFFFAOYSA-N 0.000 claims description 2
- QVJISOGPNWUYBI-UHFFFAOYSA-N ethyl n-[2-amino-4-[(3-methylthiophen-2-yl)methylamino]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1NCC1=C(C)C=CS1 QVJISOGPNWUYBI-UHFFFAOYSA-N 0.000 claims description 2
- BSQFTTSXMOOOGH-UHFFFAOYSA-N ethyl n-[2-amino-4-[(4-bromo-3-methoxythiophen-2-yl)methylamino]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1NCC1=C(OC)C(Br)=CS1 BSQFTTSXMOOOGH-UHFFFAOYSA-N 0.000 claims description 2
- HJHXJDJGCMMSGX-UHFFFAOYSA-N ethyl n-[2-amino-4-[(4-bromothiophen-2-yl)methylamino]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1NCC1=CC(Br)=CS1 HJHXJDJGCMMSGX-UHFFFAOYSA-N 0.000 claims description 2
- PZWXBOANAHDGDV-UHFFFAOYSA-N ethyl n-[2-amino-4-[(4-butylanilino)methyl]phenyl]carbamate Chemical compound C1=CC(CCCC)=CC=C1NCC1=CC=C(NC(=O)OCC)C(N)=C1 PZWXBOANAHDGDV-UHFFFAOYSA-N 0.000 claims description 2
- UACNDMSYYWUJNP-UHFFFAOYSA-N ethyl n-[2-amino-4-[(4-chloro-3-fluoroanilino)methyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1CNC1=CC=C(Cl)C(F)=C1 UACNDMSYYWUJNP-UHFFFAOYSA-N 0.000 claims description 2
- DWSPCTCHYKCYFR-UHFFFAOYSA-N ethyl n-[2-amino-4-[(4-chloroanilino)methyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1CNC1=CC=C(Cl)C=C1 DWSPCTCHYKCYFR-UHFFFAOYSA-N 0.000 claims description 2
- BYARLUNDODGUSF-UHFFFAOYSA-N ethyl n-[2-amino-4-[(4-cyanoanilino)methyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1CNC1=CC=C(C#N)C=C1 BYARLUNDODGUSF-UHFFFAOYSA-N 0.000 claims description 2
- LLYSQBCINNSNKO-UHFFFAOYSA-N ethyl n-[2-amino-4-[(4-cyclohexylanilino)methyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1CNC1=CC=C(C2CCCCC2)C=C1 LLYSQBCINNSNKO-UHFFFAOYSA-N 0.000 claims description 2
- NQNXMCDBIPXRFF-UHFFFAOYSA-N ethyl n-[2-amino-4-[(4-fluoroanilino)methyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1CNC1=CC=C(F)C=C1 NQNXMCDBIPXRFF-UHFFFAOYSA-N 0.000 claims description 2
- BSCJHOFVPMMXGC-UHFFFAOYSA-N ethyl n-[2-amino-4-[(4-methoxyanilino)methyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1CNC1=CC=C(OC)C=C1 BSCJHOFVPMMXGC-UHFFFAOYSA-N 0.000 claims description 2
- CIYWTQMAZIEXNG-UHFFFAOYSA-N ethyl n-[2-amino-4-[(4-methylanilino)methyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1CNC1=CC=C(C)C=C1 CIYWTQMAZIEXNG-UHFFFAOYSA-N 0.000 claims description 2
- NVOFZLPWTFWFDQ-UHFFFAOYSA-N ethyl n-[2-amino-4-[(4-phenylanilino)methyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1CNC1=CC=C(C=2C=CC=CC=2)C=C1 NVOFZLPWTFWFDQ-UHFFFAOYSA-N 0.000 claims description 2
- OVMRYCWHBHWHDB-UHFFFAOYSA-N ethyl n-[2-amino-4-[(4-propan-2-ylanilino)methyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1CNC1=CC=C(C(C)C)C=C1 OVMRYCWHBHWHDB-UHFFFAOYSA-N 0.000 claims description 2
- YGDMFPQYDCZIMM-UHFFFAOYSA-N ethyl n-[2-amino-4-[(4-tert-butylanilino)methyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1CNC1=CC=C(C(C)(C)C)C=C1 YGDMFPQYDCZIMM-UHFFFAOYSA-N 0.000 claims description 2
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- ITKAHTLJWIBUCZ-UHFFFAOYSA-N ethyl n-[2-amino-4-[(5-fluorothiophen-2-yl)methylamino]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1NCC1=CC=C(F)S1 ITKAHTLJWIBUCZ-UHFFFAOYSA-N 0.000 claims description 2
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- PNYDZEMORIWFHF-UHFFFAOYSA-N ethyl n-[2-amino-4-[(5-phenylthiophen-2-yl)methylamino]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1NCC1=CC=C(C=2C=CC=CC=2)S1 PNYDZEMORIWFHF-UHFFFAOYSA-N 0.000 claims description 2
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- VRXUASWAYZPEHF-UHFFFAOYSA-N ethyl n-[2-amino-4-[1-[4-(trifluoromethyl)anilino]ethyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1C(C)NC1=CC=C(C(F)(F)F)C=C1 VRXUASWAYZPEHF-UHFFFAOYSA-N 0.000 claims description 2
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- PYVCGNWJTVIAMS-UHFFFAOYSA-N ethyl n-[2-amino-4-[[3-fluoro-4-(trifluoromethyl)anilino]methyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1CNC1=CC=C(C(F)(F)F)C(F)=C1 PYVCGNWJTVIAMS-UHFFFAOYSA-N 0.000 claims description 2
- CBUCMNUGRUKIBK-UHFFFAOYSA-N ethyl n-[2-amino-4-[[4-(trifluoromethyl)anilino]methyl]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1CNC1=CC=C(C(F)(F)F)C=C1 CBUCMNUGRUKIBK-UHFFFAOYSA-N 0.000 claims description 2
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- AQQQGRCQQUTKHH-UHFFFAOYSA-N ethyl n-[2-amino-4-[methyl-[(5-methylthiophen-2-yl)methyl]amino]phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1N(C)CC1=CC=C(C)S1 AQQQGRCQQUTKHH-UHFFFAOYSA-N 0.000 claims description 2
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- PJQJLRQLLHQJMP-UHFFFAOYSA-N ethyl n-[2-chloro-4-[(3,4-dichloroanilino)methyl]phenyl]carbamate Chemical compound C1=C(Cl)C(NC(=O)OCC)=CC=C1CNC1=CC=C(Cl)C(Cl)=C1 PJQJLRQLLHQJMP-UHFFFAOYSA-N 0.000 claims description 2
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- YZOXDNFQASBYLT-UHFFFAOYSA-N ethyl n-[2-chloro-4-[(4-chloro-3-fluoroanilino)methyl]phenyl]carbamate Chemical compound C1=C(Cl)C(NC(=O)OCC)=CC=C1CNC1=CC=C(Cl)C(F)=C1 YZOXDNFQASBYLT-UHFFFAOYSA-N 0.000 claims description 2
- URAKWDASUSFXKH-UHFFFAOYSA-N ethyl n-[2-chloro-4-[(4-chloroanilino)methyl]phenyl]carbamate Chemical compound C1=C(Cl)C(NC(=O)OCC)=CC=C1CNC1=CC=C(Cl)C=C1 URAKWDASUSFXKH-UHFFFAOYSA-N 0.000 claims description 2
- XPAYAFCWAGCEME-UHFFFAOYSA-N ethyl n-[2-chloro-4-[(4-fluoroanilino)methyl]phenyl]carbamate Chemical compound C1=C(Cl)C(NC(=O)OCC)=CC=C1CNC1=CC=C(F)C=C1 XPAYAFCWAGCEME-UHFFFAOYSA-N 0.000 claims description 2
- AMWAUBYTNYONBR-UHFFFAOYSA-N ethyl n-[2-chloro-4-[(4-propan-2-ylphenyl)methylamino]phenyl]carbamate Chemical compound C1=C(Cl)C(NC(=O)OCC)=CC=C1NCC1=CC=C(C(C)C)C=C1 AMWAUBYTNYONBR-UHFFFAOYSA-N 0.000 claims description 2
- UJHAKAHMBMEMNW-UHFFFAOYSA-N ethyl n-[2-chloro-4-[(5-chlorothiophen-2-yl)methylamino]phenyl]carbamate Chemical compound C1=C(Cl)C(NC(=O)OCC)=CC=C1NCC1=CC=C(Cl)S1 UJHAKAHMBMEMNW-UHFFFAOYSA-N 0.000 claims description 2
- UVHHGQGCILHVPA-UHFFFAOYSA-N ethyl n-[2-chloro-4-[methyl-[(4-methylsulfanylphenyl)methyl]amino]phenyl]carbamate Chemical compound C1=C(Cl)C(NC(=O)OCC)=CC=C1N(C)CC1=CC=C(SC)C=C1 UVHHGQGCILHVPA-UHFFFAOYSA-N 0.000 claims description 2
- PXJYWPAJYQOYAU-UHFFFAOYSA-N ethyl n-[2-chloro-4-[methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]phenyl]carbamate Chemical compound C1=C(Cl)C(NC(=O)OCC)=CC=C1N(C)CC1=CC=C(C(F)(F)F)C=C1 PXJYWPAJYQOYAU-UHFFFAOYSA-N 0.000 claims description 2
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- FBWLGGCIJQPAGG-UHFFFAOYSA-N ethyl n-[2-fluoro-4-[[4-(trifluoromethyl)anilino]methyl]phenyl]carbamate Chemical compound C1=C(F)C(NC(=O)OCC)=CC=C1CNC1=CC=C(C(F)(F)F)C=C1 FBWLGGCIJQPAGG-UHFFFAOYSA-N 0.000 claims description 2
- HIFLWUPIVYIOKB-UHFFFAOYSA-N ethyl n-[2-methoxy-4-[(3-methylthiophen-2-yl)methylamino]phenyl]carbamate Chemical compound C1=C(OC)C(NC(=O)OCC)=CC=C1NCC1=C(C)C=CS1 HIFLWUPIVYIOKB-UHFFFAOYSA-N 0.000 claims description 2
- DBGKFRUFUABFLM-UHFFFAOYSA-N ethyl n-[2-methoxy-4-[(4-propan-2-ylphenyl)methylamino]phenyl]carbamate Chemical compound C1=C(OC)C(NC(=O)OCC)=CC=C1NCC1=CC=C(C(C)C)C=C1 DBGKFRUFUABFLM-UHFFFAOYSA-N 0.000 claims description 2
- GPLMHGDAOVFNCU-UHFFFAOYSA-N ethyl n-[2-methyl-4-[(4-propan-2-ylphenyl)methylamino]phenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCC)=CC=C1NCC1=CC=C(C(C)C)C=C1 GPLMHGDAOVFNCU-UHFFFAOYSA-N 0.000 claims description 2
- VLIKNAITKKRTJV-UHFFFAOYSA-N ethyl n-[2-methyl-4-[(5-phenylthiophen-2-yl)methylamino]phenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCC)=CC=C1NCC1=CC=C(C=2C=CC=CC=2)S1 VLIKNAITKKRTJV-UHFFFAOYSA-N 0.000 claims description 2
- YETJUQCNPAAANG-UHFFFAOYSA-N ethyl n-[2-methyl-4-[[4-(trifluoromethyl)anilino]methyl]phenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCC)=CC=C1CNC1=CC=C(C(F)(F)F)C=C1 YETJUQCNPAAANG-UHFFFAOYSA-N 0.000 claims description 2
- FJGJSYHAKOHFMZ-UHFFFAOYSA-N ethyl n-[2-methyl-4-[[4-(trifluoromethyl)phenyl]methylamino]phenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCC)=CC=C1NCC1=CC=C(C(F)(F)F)C=C1 FJGJSYHAKOHFMZ-UHFFFAOYSA-N 0.000 claims description 2
- XYIVNKLPSJLTHT-UHFFFAOYSA-N ethyl n-[4-(1,3-benzodioxol-5-ylmethylamino)-2-propan-2-yloxyphenyl]carbamate Chemical compound C1=C(OC(C)C)C(NC(=O)OCC)=CC=C1NCC1=CC=C(OCO2)C2=C1 XYIVNKLPSJLTHT-UHFFFAOYSA-N 0.000 claims description 2
- LBPNSUIVYSELKA-UHFFFAOYSA-N ethyl n-[4-(1-benzothiophen-2-ylmethylamino)-2-chlorophenyl]carbamate Chemical compound C1=C(Cl)C(NC(=O)OCC)=CC=C1NCC1=CC2=CC=CC=C2S1 LBPNSUIVYSELKA-UHFFFAOYSA-N 0.000 claims description 2
- MBZCXPYDDKNMKD-UHFFFAOYSA-N ethyl n-[4-(1-benzothiophen-2-ylmethylamino)-2-methylphenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCC)=CC=C1NCC1=CC2=CC=CC=C2S1 MBZCXPYDDKNMKD-UHFFFAOYSA-N 0.000 claims description 2
- DTOYTZIERSGENB-UHFFFAOYSA-N ethyl n-[4-(1-benzothiophen-3-ylmethylamino)-2-cyclopentyloxyphenyl]carbamate Chemical compound CCOC(=O)NC1=CC=C(NCC=2C3=CC=CC=C3SC=2)C=C1OC1CCCC1 DTOYTZIERSGENB-UHFFFAOYSA-N 0.000 claims description 2
- XDKSFHCRKBLVPN-UHFFFAOYSA-N ethyl n-[4-[(2,4-difluorophenyl)methylamino]-2-methoxyphenyl]carbamate Chemical compound C1=C(OC)C(NC(=O)OCC)=CC=C1NCC1=CC=C(F)C=C1F XDKSFHCRKBLVPN-UHFFFAOYSA-N 0.000 claims description 2
- PSRTZGHRXNJOEO-UHFFFAOYSA-N ethyl n-[4-[(3,4-difluoroanilino)methyl]-2-methylphenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCC)=CC=C1CNC1=CC=C(F)C(F)=C1 PSRTZGHRXNJOEO-UHFFFAOYSA-N 0.000 claims description 2
- DHNIHGLWXHLYGU-UHFFFAOYSA-N ethyl n-[4-[(3-fluoro-2-methylphenyl)methylamino]-2-(2-phenylethoxy)phenyl]carbamate Chemical compound C1=C(OCCC=2C=CC=CC=2)C(NC(=O)OCC)=CC=C1NCC1=CC=CC(F)=C1C DHNIHGLWXHLYGU-UHFFFAOYSA-N 0.000 claims description 2
- DDLKIMUNVILAIR-UHFFFAOYSA-N ethyl n-[4-[(3-fluoro-2-methylphenyl)methylamino]-2-phenylmethoxyphenyl]carbamate Chemical compound C1=C(OCC=2C=CC=CC=2)C(NC(=O)OCC)=CC=C1NCC1=CC=CC(F)=C1C DDLKIMUNVILAIR-UHFFFAOYSA-N 0.000 claims description 2
- CVTJQRXEUAZWTQ-UHFFFAOYSA-N ethyl n-[4-[(3-fluoro-2-methylphenyl)methylamino]-2-propan-2-yloxyphenyl]carbamate Chemical compound C1=C(OC(C)C)C(NC(=O)OCC)=CC=C1NCC1=CC=CC(F)=C1C CVTJQRXEUAZWTQ-UHFFFAOYSA-N 0.000 claims description 2
- QEYNFGCIULPLPC-UHFFFAOYSA-N ethyl n-[4-[(3-fluoroanilino)methyl]-2,6-dimethylphenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCC)=C(C)C=C1CNC1=CC=CC(F)=C1 QEYNFGCIULPLPC-UHFFFAOYSA-N 0.000 claims description 2
- YFYLMPIYVCSHPH-UHFFFAOYSA-N ethyl n-[4-[(3-fluoroanilino)methyl]-2-methylphenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCC)=CC=C1CNC1=CC=CC(F)=C1 YFYLMPIYVCSHPH-UHFFFAOYSA-N 0.000 claims description 2
- IMLUDSPLHDRIPO-UHFFFAOYSA-N ethyl n-[4-[(3-fluorophenyl)methylamino]-2-methoxyphenyl]carbamate Chemical compound C1=C(OC)C(NC(=O)OCC)=CC=C1NCC1=CC=CC(F)=C1 IMLUDSPLHDRIPO-UHFFFAOYSA-N 0.000 claims description 2
- LCEODKNUZATZLW-UHFFFAOYSA-N ethyl n-[4-[(3-methoxyphenyl)methylamino]-2-phenylmethoxyphenyl]carbamate Chemical compound C1=C(OCC=2C=CC=CC=2)C(NC(=O)OCC)=CC=C1NCC1=CC=CC(OC)=C1 LCEODKNUZATZLW-UHFFFAOYSA-N 0.000 claims description 2
- TZNQYORNTRQEJV-UHFFFAOYSA-N ethyl n-[4-[(4-chloro-3-fluoroanilino)methyl]-2-fluorophenyl]carbamate Chemical compound C1=C(F)C(NC(=O)OCC)=CC=C1CNC1=CC=C(Cl)C(F)=C1 TZNQYORNTRQEJV-UHFFFAOYSA-N 0.000 claims description 2
- RUVLMXALVIBXME-UHFFFAOYSA-N ethyl n-[4-[(4-chloroanilino)methyl]-2-fluorophenyl]carbamate Chemical compound C1=C(F)C(NC(=O)OCC)=CC=C1CNC1=CC=C(Cl)C=C1 RUVLMXALVIBXME-UHFFFAOYSA-N 0.000 claims description 2
- DPIDNSCETUXASM-UHFFFAOYSA-N ethyl n-[4-[(4-chloroanilino)methyl]-2-methylphenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCC)=CC=C1CNC1=CC=C(Cl)C=C1 DPIDNSCETUXASM-UHFFFAOYSA-N 0.000 claims description 2
- JRMWXXMVCOHXCB-UHFFFAOYSA-N ethyl n-[4-[(4-chloroanilino)methyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1CNC1=CC=C(Cl)C=C1 JRMWXXMVCOHXCB-UHFFFAOYSA-N 0.000 claims description 2
- QCEHDLKQWVGPFI-UHFFFAOYSA-N ethyl n-[4-[(4-chlorophenyl)methylamino]-2-methylphenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCC)=CC=C1NCC1=CC=C(Cl)C=C1 QCEHDLKQWVGPFI-UHFFFAOYSA-N 0.000 claims description 2
- HCLUFHIOGAXFCC-UHFFFAOYSA-N ethyl n-[4-[(4-fluoroanilino)methyl]-2-methylphenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCC)=CC=C1CNC1=CC=C(F)C=C1 HCLUFHIOGAXFCC-UHFFFAOYSA-N 0.000 claims description 2
- NWLXPWFNBKJVKX-UHFFFAOYSA-N ethyl n-[4-[(4-fluorophenyl)methyl-methylamino]-2-propan-2-yloxyphenyl]carbamate Chemical compound C1=C(OC(C)C)C(NC(=O)OCC)=CC=C1N(C)CC1=CC=C(F)C=C1 NWLXPWFNBKJVKX-UHFFFAOYSA-N 0.000 claims description 2
- XKSCLMWYIAIGGH-UHFFFAOYSA-N ethyl n-[4-[(4-methylsulfanylphenyl)methylamino]-2-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(NC(=O)OCC)=CC=C1NCC1=CC=C(SC)C=C1 XKSCLMWYIAIGGH-UHFFFAOYSA-N 0.000 claims description 2
- FUOWMPZQNQMKQJ-UHFFFAOYSA-N ethyl n-[4-[(4-methylsulfanylphenyl)methylamino]-2-phenylmethoxyphenyl]carbamate Chemical compound C1=C(OCC=2C=CC=CC=2)C(NC(=O)OCC)=CC=C1NCC1=CC=C(SC)C=C1 FUOWMPZQNQMKQJ-UHFFFAOYSA-N 0.000 claims description 2
- KKLHNPWQODPAQP-UHFFFAOYSA-N ethyl n-[4-[(4-tert-butylphenyl)methyl-methylamino]-2-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(NC(=O)OCC)=CC=C1N(C)CC1=CC=C(C(C)(C)C)C=C1 KKLHNPWQODPAQP-UHFFFAOYSA-N 0.000 claims description 2
- AYJLXGFLEJCNSS-UHFFFAOYSA-N ethyl n-[4-[(4-tert-butylphenyl)methyl-methylamino]-2-chlorophenyl]carbamate Chemical compound C1=C(Cl)C(NC(=O)OCC)=CC=C1N(C)CC1=CC=C(C(C)(C)C)C=C1 AYJLXGFLEJCNSS-UHFFFAOYSA-N 0.000 claims description 2
- JHNNJXNHEUWQQI-UHFFFAOYSA-N ethyl n-[4-[(4-tert-butylphenyl)methylamino]-2-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(NC(=O)OCC)=CC=C1NCC1=CC=C(C(C)(C)C)C=C1 JHNNJXNHEUWQQI-UHFFFAOYSA-N 0.000 claims description 2
- LZCPHDBEDLLPCH-UHFFFAOYSA-N ethyl n-[4-[(5-bromothiophen-2-yl)methyl-methylamino]-2-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(NC(=O)OCC)=CC=C1N(C)CC1=CC=C(Br)S1 LZCPHDBEDLLPCH-UHFFFAOYSA-N 0.000 claims description 2
- CZIYBKSESQHEMY-UHFFFAOYSA-N ethyl n-[4-[(5-bromothiophen-2-yl)methylamino]-2-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(NC(=O)OCC)=CC=C1NCC1=CC=C(Br)S1 CZIYBKSESQHEMY-UHFFFAOYSA-N 0.000 claims description 2
- BNRZQCLVVKMSIW-UHFFFAOYSA-N ethyl n-[4-[(5-bromothiophen-2-yl)methylamino]-2-chlorophenyl]carbamate Chemical compound C1=C(Cl)C(NC(=O)OCC)=CC=C1NCC1=CC=C(Br)S1 BNRZQCLVVKMSIW-UHFFFAOYSA-N 0.000 claims description 2
- URCRJUUPLVVVDL-UHFFFAOYSA-N ethyl n-[4-[(5-chlorothiophen-2-yl)methyl-methylamino]-2-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(NC(=O)OCC)=CC=C1N(C)CC1=CC=C(Cl)S1 URCRJUUPLVVVDL-UHFFFAOYSA-N 0.000 claims description 2
- AKLXLTKONNDHHV-UHFFFAOYSA-N ethyl n-[4-[(5-chlorothiophen-2-yl)methylamino]-2-(6-methoxypyridin-3-yl)phenyl]carbamate Chemical compound C1=C(C=2C=NC(OC)=CC=2)C(NC(=O)OCC)=CC=C1NCC1=CC=C(Cl)S1 AKLXLTKONNDHHV-UHFFFAOYSA-N 0.000 claims description 2
- JBIFACVOFRVYLT-UHFFFAOYSA-N ethyl n-[4-[(5-chlorothiophen-2-yl)methylamino]-2-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(NC(=O)OCC)=CC=C1NCC1=CC=C(Cl)S1 JBIFACVOFRVYLT-UHFFFAOYSA-N 0.000 claims description 2
- XXUITLDPXQQWMX-UHFFFAOYSA-N ethyl n-[4-[(5-chlorothiophen-2-yl)methylamino]-2-cyanophenyl]carbamate Chemical compound C1=C(C#N)C(NC(=O)OCC)=CC=C1NCC1=CC=C(Cl)S1 XXUITLDPXQQWMX-UHFFFAOYSA-N 0.000 claims description 2
- PPNRDWUDMHIESH-UHFFFAOYSA-N ethyl n-[4-[(5-chlorothiophen-2-yl)methylamino]-2-iodophenyl]carbamate Chemical compound C1=C(I)C(NC(=O)OCC)=CC=C1NCC1=CC=C(Cl)S1 PPNRDWUDMHIESH-UHFFFAOYSA-N 0.000 claims description 2
- ZWTUCGJBUWCVJO-UHFFFAOYSA-N ethyl n-[4-[(5-chlorothiophen-2-yl)methylamino]-2-methylphenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCC)=CC=C1NCC1=CC=C(Cl)S1 ZWTUCGJBUWCVJO-UHFFFAOYSA-N 0.000 claims description 2
- BHONFRQFLYRMJR-UHFFFAOYSA-N ethyl n-[4-[(5-chlorothiophen-2-yl)methylamino]-2-pyridin-3-ylphenyl]carbamate Chemical compound C1=C(C=2C=NC=CC=2)C(NC(=O)OCC)=CC=C1NCC1=CC=C(Cl)S1 BHONFRQFLYRMJR-UHFFFAOYSA-N 0.000 claims description 2
- HWRLUDVUXQLMIH-UHFFFAOYSA-N ethyl n-[4-[(5-chlorothiophen-2-yl)methylamino]-2-pyridin-4-ylphenyl]carbamate Chemical compound C1=C(C=2C=CN=CC=2)C(NC(=O)OCC)=CC=C1NCC1=CC=C(Cl)S1 HWRLUDVUXQLMIH-UHFFFAOYSA-N 0.000 claims description 2
- PCPKDKGFFJFEJT-UHFFFAOYSA-N ethyl n-[4-[(5-chlorothiophen-2-yl)methylamino]-2-quinolin-3-ylphenyl]carbamate Chemical compound C1=C(C=2C=C3C=CC=CC3=NC=2)C(NC(=O)OCC)=CC=C1NCC1=CC=C(Cl)S1 PCPKDKGFFJFEJT-UHFFFAOYSA-N 0.000 claims description 2
- NIEWPONKIRMTPH-UHFFFAOYSA-N ethyl n-[4-[(6-methoxy-1-benzothiophen-2-yl)methylamino]-2-methylphenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCC)=CC=C1NCC1=CC2=CC=C(OC)C=C2S1 NIEWPONKIRMTPH-UHFFFAOYSA-N 0.000 claims description 2
- UNHRXQWFNONDJR-UHFFFAOYSA-N ethyl n-[4-[1-(4-chloroanilino)ethyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1C(C)NC1=CC=C(Cl)C=C1 UNHRXQWFNONDJR-UHFFFAOYSA-N 0.000 claims description 2
- KLNBESIFXRZEPF-UHFFFAOYSA-N ethyl n-[4-[[3-fluoro-4-(trifluoromethyl)phenyl]methylamino]-2-methylphenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCC)=CC=C1NCC1=CC=C(C(F)(F)F)C(F)=C1 KLNBESIFXRZEPF-UHFFFAOYSA-N 0.000 claims description 2
- GCFCPEZENZTFAY-UHFFFAOYSA-N ethyl n-[4-[[4-(trifluoromethyl)anilino]methyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1CNC1=CC=C(C(F)(F)F)C=C1 GCFCPEZENZTFAY-UHFFFAOYSA-N 0.000 claims description 2
- GAYMQGPGTVLOQU-UHFFFAOYSA-N ethyl n-[4-[methyl-[(4-methylsulfanylphenyl)methyl]amino]-2-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(NC(=O)OCC)=CC=C1N(C)CC1=CC=C(SC)C=C1 GAYMQGPGTVLOQU-UHFFFAOYSA-N 0.000 claims description 2
- IMUOXPRZLBQDQK-UHFFFAOYSA-N ethyl n-[4-[methyl-[(4-propan-2-ylphenyl)methyl]amino]-2-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(NC(=O)OCC)=CC=C1N(C)CC1=CC=C(C(C)C)C=C1 IMUOXPRZLBQDQK-UHFFFAOYSA-N 0.000 claims description 2
- LUCIULMHEDDUDH-UHFFFAOYSA-N ethyl n-[4-[methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(C(F)(F)F)C(NC(=O)OCC)=CC=C1N(C)CC1=CC=C(C(F)(F)F)C=C1 LUCIULMHEDDUDH-UHFFFAOYSA-N 0.000 claims description 2
- JLNYLDRCNCLJQY-UHFFFAOYSA-N hexyl n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]carbamate Chemical compound C1=C(Cl)C(NC(=O)OCCCCCC)=CC=C1N(C)CC1=CC=C(Cl)S1 JLNYLDRCNCLJQY-UHFFFAOYSA-N 0.000 claims description 2
- 230000008449 language Effects 0.000 claims description 2
- 230000001404 mediated effect Effects 0.000 claims description 2
- ZWBZSWWTAABAAW-UHFFFAOYSA-N methyl 3-[4-[(5-chlorothiophen-2-yl)methyl-methylamino]-2-methylanilino]-3-oxopropanoate Chemical compound C1=C(C)C(NC(=O)CC(=O)OC)=CC=C1N(C)CC1=CC=C(Cl)S1 ZWBZSWWTAABAAW-UHFFFAOYSA-N 0.000 claims description 2
- GIOTXFVSHZODRM-UHFFFAOYSA-N methyl 4-[[3-methyl-4-(propoxycarbonylamino)anilino]methyl]benzoate Chemical compound C1=C(C)C(NC(=O)OCCC)=CC=C1NCC1=CC=C(C(=O)OC)C=C1 GIOTXFVSHZODRM-UHFFFAOYSA-N 0.000 claims description 2
- ZRCLMLJAAYQKFH-UHFFFAOYSA-N methyl n-[4-(1-benzothiophen-2-ylmethylamino)-2-methoxyphenyl]carbamate Chemical compound C1=C(OC)C(NC(=O)OC)=CC=C1NCC1=CC2=CC=CC=C2S1 ZRCLMLJAAYQKFH-UHFFFAOYSA-N 0.000 claims description 2
- NSXYSIRPQHZGRS-UHFFFAOYSA-N n-(2,4-dimethyl-6-morpholin-4-ylpyridin-3-yl)-2-(3,4-dimethylphenyl)acetamide Chemical compound C1=C(C)C(C)=CC=C1CC(=O)NC1=C(C)C=C(N2CCOCC2)N=C1C NSXYSIRPQHZGRS-UHFFFAOYSA-N 0.000 claims description 2
- QFXOZVHCESXJLE-UHFFFAOYSA-N n-(2,4-dimethyl-6-morpholin-4-ylpyridin-3-yl)-2-(3,5-dimethylphenyl)acetamide Chemical compound CC1=CC(C)=CC(CC(=O)NC=2C(=NC(=CC=2C)N2CCOCC2)C)=C1 QFXOZVHCESXJLE-UHFFFAOYSA-N 0.000 claims description 2
- LNHWKNMHQDEDHA-UHFFFAOYSA-N n-(2,4-dimethyl-6-morpholin-4-ylpyridin-3-yl)-2-(3-fluorophenyl)acetamide Chemical compound CC1=CC(N2CCOCC2)=NC(C)=C1NC(=O)CC1=CC=CC(F)=C1 LNHWKNMHQDEDHA-UHFFFAOYSA-N 0.000 claims description 2
- MTXSFPSKHDODED-UHFFFAOYSA-N n-(2,4-dimethyl-6-morpholin-4-ylpyridin-3-yl)-2-(3-methylphenyl)acetamide Chemical compound CC1=CC=CC(CC(=O)NC=2C(=NC(=CC=2C)N2CCOCC2)C)=C1 MTXSFPSKHDODED-UHFFFAOYSA-N 0.000 claims description 2
- LXXQJPDIABMXEO-UHFFFAOYSA-N n-(2,4-dimethyl-6-morpholin-4-ylpyridin-3-yl)-2-(4-fluorophenyl)acetamide Chemical compound CC1=CC(N2CCOCC2)=NC(C)=C1NC(=O)CC1=CC=C(F)C=C1 LXXQJPDIABMXEO-UHFFFAOYSA-N 0.000 claims description 2
- RVOCAYGOJGYTFK-UHFFFAOYSA-N n-(2,4-dimethyl-6-morpholin-4-ylpyridin-3-yl)-2-(4-methoxy-3-methylphenyl)acetamide Chemical compound C1=C(C)C(OC)=CC=C1CC(=O)NC1=C(C)C=C(N2CCOCC2)N=C1C RVOCAYGOJGYTFK-UHFFFAOYSA-N 0.000 claims description 2
- ZWAWWLRQLGIARH-UHFFFAOYSA-N n-(2,4-dimethyl-6-morpholin-4-ylpyridin-3-yl)-2-(4-methoxyphenyl)acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)NC1=C(C)C=C(N2CCOCC2)N=C1C ZWAWWLRQLGIARH-UHFFFAOYSA-N 0.000 claims description 2
- ZZQZQXDYSRXASP-UHFFFAOYSA-N n-(2,4-dimethyl-6-morpholin-4-ylpyridin-3-yl)-2-(4-methylphenyl)acetamide Chemical compound C1=CC(C)=CC=C1CC(=O)NC1=C(C)C=C(N2CCOCC2)N=C1C ZZQZQXDYSRXASP-UHFFFAOYSA-N 0.000 claims description 2
- OEMGVWLOWRPQLL-UHFFFAOYSA-N n-(2,4-dimethyl-6-morpholin-4-ylpyridin-3-yl)-2-[3-(trifluoromethyl)phenyl]acetamide Chemical compound CC1=CC(N2CCOCC2)=NC(C)=C1NC(=O)CC1=CC=CC(C(F)(F)F)=C1 OEMGVWLOWRPQLL-UHFFFAOYSA-N 0.000 claims description 2
- GKDVUJSUFGQXKA-UHFFFAOYSA-N n-(2,4-dimethyl-6-morpholin-4-ylpyridin-3-yl)-2-naphthalen-2-ylacetamide Chemical compound N=1C(C)=C(NC(=O)CC=2C=C3C=CC=CC3=CC=2)C(C)=CC=1N1CCOCC1 GKDVUJSUFGQXKA-UHFFFAOYSA-N 0.000 claims description 2
- LOCRXXVELNBLQE-UHFFFAOYSA-N n-(2,4-dimethyl-6-morpholin-4-ylpyridin-3-yl)-2-phenylacetamide Chemical compound CC1=CC(N2CCOCC2)=NC(C)=C1NC(=O)CC1=CC=CC=C1 LOCRXXVELNBLQE-UHFFFAOYSA-N 0.000 claims description 2
- MRNPWIWBKMYBTH-UHFFFAOYSA-N n-(2,4-dimethyl-6-morpholin-4-ylpyridin-3-yl)-2-phenylcyclopropane-1-carboxamide Chemical compound CC1=CC(N2CCOCC2)=NC(C)=C1NC(=O)C1CC1C1=CC=CC=C1 MRNPWIWBKMYBTH-UHFFFAOYSA-N 0.000 claims description 2
- VRDZAGWZCGIZSC-UHFFFAOYSA-N n-(2,4-dimethyl-6-morpholin-4-ylpyridin-3-yl)-2-thiophen-2-ylacetamide Chemical compound CC1=CC(N2CCOCC2)=NC(C)=C1NC(=O)CC1=CC=CS1 VRDZAGWZCGIZSC-UHFFFAOYSA-N 0.000 claims description 2
- ZBQQCPVAXQILBE-UHFFFAOYSA-N n-(2,4-dimethyl-6-morpholin-4-ylpyridin-3-yl)-2-thiophen-3-ylacetamide Chemical compound CC1=CC(N2CCOCC2)=NC(C)=C1NC(=O)CC=1C=CSC=1 ZBQQCPVAXQILBE-UHFFFAOYSA-N 0.000 claims description 2
- WVSKXMHDWLIKIR-UHFFFAOYSA-N n-(2,4-dimethyl-6-morpholin-4-ylpyridin-3-yl)-3,5,5-trimethylhexanamide Chemical compound N1=C(C)C(NC(=O)CC(C)CC(C)(C)C)=C(C)C=C1N1CCOCC1 WVSKXMHDWLIKIR-UHFFFAOYSA-N 0.000 claims description 2
- KAKNMOGUWPXQFL-UHFFFAOYSA-N n-(2,4-dimethyl-6-morpholin-4-ylpyridin-3-yl)-3-(4-methoxyphenyl)propanamide Chemical compound C1=CC(OC)=CC=C1CCC(=O)NC1=C(C)C=C(N2CCOCC2)N=C1C KAKNMOGUWPXQFL-UHFFFAOYSA-N 0.000 claims description 2
- OFNMXZJAGVKVKO-UHFFFAOYSA-N n-(2,4-dimethyl-6-morpholin-4-ylpyridin-3-yl)-3-(4-methylphenyl)propanamide Chemical compound C1=CC(C)=CC=C1CCC(=O)NC1=C(C)C=C(N2CCOCC2)N=C1C OFNMXZJAGVKVKO-UHFFFAOYSA-N 0.000 claims description 2
- BLESCNKLEXGCBO-UHFFFAOYSA-N n-(2,4-dimethyl-6-morpholin-4-ylpyridin-3-yl)-4-methylpentanamide Chemical compound N1=C(C)C(NC(=O)CCC(C)C)=C(C)C=C1N1CCOCC1 BLESCNKLEXGCBO-UHFFFAOYSA-N 0.000 claims description 2
- LRPPLNWCCXUMIQ-UHFFFAOYSA-N n-(2,4-dimethyl-6-morpholin-4-ylpyridin-3-yl)-5-methylhexanamide Chemical compound N1=C(C)C(NC(=O)CCCC(C)C)=C(C)C=C1N1CCOCC1 LRPPLNWCCXUMIQ-UHFFFAOYSA-N 0.000 claims description 2
- RZPBJOUKSLGPAK-UHFFFAOYSA-N n-(2,4-dimethyl-6-morpholin-4-ylpyridin-3-yl)heptanamide Chemical compound N1=C(C)C(NC(=O)CCCCCC)=C(C)C=C1N1CCOCC1 RZPBJOUKSLGPAK-UHFFFAOYSA-N 0.000 claims description 2
- QHRDANBBSJKUAT-UHFFFAOYSA-N n-(2,4-dimethyl-6-morpholin-4-ylpyridin-3-yl)octanamide Chemical compound N1=C(C)C(NC(=O)CCCCCCC)=C(C)C=C1N1CCOCC1 QHRDANBBSJKUAT-UHFFFAOYSA-N 0.000 claims description 2
- UANXUOHOUIPKAT-UHFFFAOYSA-N n-(2,4-dimethyl-6-quinolin-3-ylphenyl)-2-(4-fluorophenyl)acetamide Chemical compound C=1N=C2C=CC=CC2=CC=1C1=CC(C)=CC(C)=C1NC(=O)CC1=CC=C(F)C=C1 UANXUOHOUIPKAT-UHFFFAOYSA-N 0.000 claims description 2
- QFBRGGLYIZJDNP-UHFFFAOYSA-N n-(2,6-difluoro-4-morpholin-4-ylphenyl)-2-(3-fluorophenyl)acetamide Chemical compound FC1=CC=CC(CC(=O)NC=2C(=CC(=CC=2F)N2CCOCC2)F)=C1 QFBRGGLYIZJDNP-UHFFFAOYSA-N 0.000 claims description 2
- PCQHZOFRMZIDSO-UHFFFAOYSA-N n-(2,6-difluoro-4-morpholin-4-ylphenyl)-3,3-dimethylbutanamide Chemical compound C1=C(F)C(NC(=O)CC(C)(C)C)=C(F)C=C1N1CCOCC1 PCQHZOFRMZIDSO-UHFFFAOYSA-N 0.000 claims description 2
- RQMWEJOBHGLLHJ-UHFFFAOYSA-N n-(2,6-dimethyl-4-morpholin-4-ylphenyl)-2,3-dihydro-1-benzofuran-2-carboxamide Chemical compound C=1C(C)=C(NC(=O)C2OC3=CC=CC=C3C2)C(C)=CC=1N1CCOCC1 RQMWEJOBHGLLHJ-UHFFFAOYSA-N 0.000 claims description 2
- RZHYJMWCLWAHFW-UHFFFAOYSA-N n-(2,6-dimethyl-4-morpholin-4-ylphenyl)-2-(3,4-dimethylphenyl)acetamide Chemical compound C1=C(C)C(C)=CC=C1CC(=O)NC1=C(C)C=C(N2CCOCC2)C=C1C RZHYJMWCLWAHFW-UHFFFAOYSA-N 0.000 claims description 2
- BWTFEOVRRVXFIS-UHFFFAOYSA-N n-(2,6-dimethyl-4-morpholin-4-ylphenyl)-2-(3-fluorophenyl)acetamide Chemical compound CC1=CC(N2CCOCC2)=CC(C)=C1NC(=O)CC1=CC=CC(F)=C1 BWTFEOVRRVXFIS-UHFFFAOYSA-N 0.000 claims description 2
- BHJCRISXCWZQNL-UHFFFAOYSA-N n-(2,6-dimethyl-4-morpholin-4-ylphenyl)-2-(3-methylphenyl)acetamide Chemical compound CC1=CC=CC(CC(=O)NC=2C(=CC(=CC=2C)N2CCOCC2)C)=C1 BHJCRISXCWZQNL-UHFFFAOYSA-N 0.000 claims description 2
- FQXJKHBCIJGCQO-UHFFFAOYSA-N n-(2,6-dimethyl-4-morpholin-4-ylphenyl)-2-(4-fluorophenyl)acetamide Chemical compound CC1=CC(N2CCOCC2)=CC(C)=C1NC(=O)CC1=CC=C(F)C=C1 FQXJKHBCIJGCQO-UHFFFAOYSA-N 0.000 claims description 2
- LWXZAWFLFOVWCD-UHFFFAOYSA-N n-(2,6-dimethyl-4-morpholin-4-ylphenyl)-2-(4-methylphenyl)acetamide Chemical compound C1=CC(C)=CC=C1CC(=O)NC1=C(C)C=C(N2CCOCC2)C=C1C LWXZAWFLFOVWCD-UHFFFAOYSA-N 0.000 claims description 2
- WZSQCEVOMHBPFJ-UHFFFAOYSA-N n-(2,6-dimethyl-4-morpholin-4-ylphenyl)-2-[3-(trifluoromethyl)phenyl]acetamide Chemical compound CC1=CC(N2CCOCC2)=CC(C)=C1NC(=O)CC1=CC=CC(C(F)(F)F)=C1 WZSQCEVOMHBPFJ-UHFFFAOYSA-N 0.000 claims description 2
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- CHGPKEYXXUWPLC-UHFFFAOYSA-N n-[1-[(6-fluoro-4h-1,3-benzodioxin-8-yl)methyl]-2,3-dihydroindol-5-yl]-2-(4-fluorophenyl)acetamide Chemical compound C1=CC(F)=CC=C1CC(=O)NC1=CC=C(N(CC=2C=3OCOCC=3C=C(F)C=2)CC2)C2=C1 CHGPKEYXXUWPLC-UHFFFAOYSA-N 0.000 claims description 2
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- ZXAIVTUUGYJSJH-UHFFFAOYSA-N n-[1-[[1-(4-fluorophenyl)-5-methylpyrazol-4-yl]methyl]-2,3-dihydroindol-5-yl]-3,3-dimethylbutanamide Chemical compound CC1=C(CN2C3=CC=C(NC(=O)CC(C)(C)C)C=C3CC2)C=NN1C1=CC=C(F)C=C1 ZXAIVTUUGYJSJH-UHFFFAOYSA-N 0.000 claims description 2
- WVTBISXVGWDRJU-UHFFFAOYSA-N n-[1-[[2-chloro-5-(trifluoromethyl)phenyl]methyl]-2,3-dihydroindol-5-yl]-2-(4-fluorophenyl)acetamide Chemical compound C1=CC(F)=CC=C1CC(=O)NC1=CC=C(N(CC=2C(=CC=C(C=2)C(F)(F)F)Cl)CC2)C2=C1 WVTBISXVGWDRJU-UHFFFAOYSA-N 0.000 claims description 2
- UIPIUVZSTJLTJO-UHFFFAOYSA-N n-[1-[[2-chloro-5-(trifluoromethyl)phenyl]methyl]-2,3-dihydroindol-5-yl]-3,3-dimethylbutanamide Chemical compound C1CC2=CC(NC(=O)CC(C)(C)C)=CC=C2N1CC1=CC(C(F)(F)F)=CC=C1Cl UIPIUVZSTJLTJO-UHFFFAOYSA-N 0.000 claims description 2
- SYJPKVCEZJKYPM-UHFFFAOYSA-N n-[1-[[3-fluoro-4-(trifluoromethyl)phenyl]methyl]-2,3-dihydroindol-5-yl]-3,3-dimethylbutanamide Chemical compound C1CC2=CC(NC(=O)CC(C)(C)C)=CC=C2N1CC1=CC=C(C(F)(F)F)C(F)=C1 SYJPKVCEZJKYPM-UHFFFAOYSA-N 0.000 claims description 2
- CBTMVBYHAPYJDV-UHFFFAOYSA-N n-[1-[[5-(4-chlorophenoxy)-1,3-dimethylpyrazol-4-yl]methyl]-2,3-dihydroindol-5-yl]-2-(4-fluorophenyl)acetamide Chemical compound C1CC2=CC(NC(=O)CC=3C=CC(F)=CC=3)=CC=C2N1CC=1C(C)=NN(C)C=1OC1=CC=C(Cl)C=C1 CBTMVBYHAPYJDV-UHFFFAOYSA-N 0.000 claims description 2
- MCAYBEOKXFMNSH-UHFFFAOYSA-N n-[1-[[6-(4-chlorophenyl)sulfanylpyridin-3-yl]methyl]-2,3-dihydroindol-5-yl]-3,3-dimethylbutanamide Chemical compound C1CC2=CC(NC(=O)CC(C)(C)C)=CC=C2N1CC(C=N1)=CC=C1SC1=CC=C(Cl)C=C1 MCAYBEOKXFMNSH-UHFFFAOYSA-N 0.000 claims description 2
- VCHXEARYOTZKNN-UHFFFAOYSA-N n-[1-[[6-(4-cyanophenoxy)pyridin-3-yl]methyl]-2,3-dihydroindol-5-yl]-2-(4-fluorophenyl)acetamide Chemical compound C1=CC(F)=CC=C1CC(=O)NC1=CC=C(N(CC=2C=NC(OC=3C=CC(=CC=3)C#N)=CC=2)CC2)C2=C1 VCHXEARYOTZKNN-UHFFFAOYSA-N 0.000 claims description 2
- DLDPSEZMOLYRJJ-UHFFFAOYSA-N n-[1-[[6-(4-cyanophenoxy)pyridin-3-yl]methyl]-2,3-dihydroindol-5-yl]-3,3-dimethylbutanamide Chemical compound C1CC2=CC(NC(=O)CC(C)(C)C)=CC=C2N1CC(C=N1)=CC=C1OC1=CC=C(C#N)C=C1 DLDPSEZMOLYRJJ-UHFFFAOYSA-N 0.000 claims description 2
- JRMUSINHKOFJFV-UHFFFAOYSA-N n-[2,4-dimethyl-6-(2,2,5-trimethyl-3h-1-benzofuran-7-yl)phenyl]-2-(4-fluorophenyl)acetamide Chemical compound C=1C(C)=CC=2CC(C)(C)OC=2C=1C1=CC(C)=CC(C)=C1NC(=O)CC1=CC=C(F)C=C1 JRMUSINHKOFJFV-UHFFFAOYSA-N 0.000 claims description 2
- XAONIUOGFLUMOE-UHFFFAOYSA-N n-[2,4-dimethyl-6-(4-propan-2-ylphenyl)phenyl]-3,3-dimethylbutanamide Chemical compound C1=CC(C(C)C)=CC=C1C1=CC(C)=CC(C)=C1NC(=O)CC(C)(C)C XAONIUOGFLUMOE-UHFFFAOYSA-N 0.000 claims description 2
- DNUHYUKYPLADFM-UHFFFAOYSA-N n-[2,4-dimethyl-6-[3-(trifluoromethoxy)phenyl]phenyl]-2-(4-fluorophenyl)acetamide Chemical compound C=1C=CC(OC(F)(F)F)=CC=1C1=CC(C)=CC(C)=C1NC(=O)CC1=CC=C(F)C=C1 DNUHYUKYPLADFM-UHFFFAOYSA-N 0.000 claims description 2
- DAVKBZXKNMPEHG-UHFFFAOYSA-N n-[2,6-dimethyl-4-[[4-(trifluoromethyl)phenyl]methylamino]phenyl]acetamide Chemical compound C1=C(C)C(NC(=O)C)=C(C)C=C1NCC1=CC=C(C(F)(F)F)C=C1 DAVKBZXKNMPEHG-UHFFFAOYSA-N 0.000 claims description 2
- BQIIVIXQLUJZJJ-UHFFFAOYSA-N n-[2,6-dimethyl-4-[[6-(trifluoromethyl)pyridin-3-yl]methylamino]phenyl]-3,3-dimethylbutanamide Chemical compound CC1=C(NC(=O)CC(C)(C)C)C(C)=CC(NCC=2C=NC(=CC=2)C(F)(F)F)=C1 BQIIVIXQLUJZJJ-UHFFFAOYSA-N 0.000 claims description 2
- NPKGBLZCKDGMPK-UHFFFAOYSA-N n-[2,6-dimethyl-4-[methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]phenyl]acetamide Chemical compound C=1C(C)=C(NC(C)=O)C(C)=CC=1N(C)CC1=CC=C(C(F)(F)F)C=C1 NPKGBLZCKDGMPK-UHFFFAOYSA-N 0.000 claims description 2
- ADEYHVVPEMWXKK-UHFFFAOYSA-N n-[2-(2,3-dihydro-1,4-benzodioxin-6-yl)-4,6-dimethylphenyl]-2-(4-fluorophenyl)acetamide Chemical compound C=1C=C2OCCOC2=CC=1C1=CC(C)=CC(C)=C1NC(=O)CC1=CC=C(F)C=C1 ADEYHVVPEMWXKK-UHFFFAOYSA-N 0.000 claims description 2
- HYADKSBTWYHMRC-UHFFFAOYSA-N n-[2-(3-acetamidophenyl)-4,6-dimethylphenyl]-2-(4-fluorophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(C=2C(=C(C)C=C(C)C=2)NC(=O)CC=2C=CC(F)=CC=2)=C1 HYADKSBTWYHMRC-UHFFFAOYSA-N 0.000 claims description 2
- XYJIVBJRAKFODH-UHFFFAOYSA-N n-[2-(3-aminophenyl)-4,6-dimethylphenyl]-2-(4-fluorophenyl)acetamide Chemical compound C=1C=CC(N)=CC=1C1=CC(C)=CC(C)=C1NC(=O)CC1=CC=C(F)C=C1 XYJIVBJRAKFODH-UHFFFAOYSA-N 0.000 claims description 2
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- KECGJWZRAYXEMQ-UHFFFAOYSA-N n-[2-(4-ethenylphenyl)-4,6-dimethylphenyl]-2-(4-fluorophenyl)acetamide Chemical compound C=1C=C(C=C)C=CC=1C1=CC(C)=CC(C)=C1NC(=O)CC1=CC=C(F)C=C1 KECGJWZRAYXEMQ-UHFFFAOYSA-N 0.000 claims description 2
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- ISMXZIBRJLAXBF-UHFFFAOYSA-N n-[2-[4-(dimethylamino)phenyl]-4,6-dimethylphenyl]-2-(4-fluorophenyl)acetamide Chemical compound C1=CC(N(C)C)=CC=C1C1=CC(C)=CC(C)=C1NC(=O)CC1=CC=C(F)C=C1 ISMXZIBRJLAXBF-UHFFFAOYSA-N 0.000 claims description 2
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- GOXFPLZEUOSYNS-UHFFFAOYSA-N n-[2-amino-4-[(5-chlorothiophen-2-yl)methylamino]phenyl]-2-(4-fluorophenyl)acetamide Chemical compound C=1C=C(NC(=O)CC=2C=CC(F)=CC=2)C(N)=CC=1NCC1=CC=C(Cl)S1 GOXFPLZEUOSYNS-UHFFFAOYSA-N 0.000 claims description 2
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- VEZLUWKLAGYAPU-UHFFFAOYSA-N n-[2-bromo-4-morpholin-4-yl-6-(trifluoromethyl)phenyl]-2-cyclopentylacetamide Chemical compound FC(F)(F)C1=CC(N2CCOCC2)=CC(Br)=C1NC(=O)CC1CCCC1 VEZLUWKLAGYAPU-UHFFFAOYSA-N 0.000 claims description 2
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- LNEODKACMQDIAF-UHFFFAOYSA-N n-[2-bromo-4-morpholin-4-yl-6-(trifluoromethyl)phenyl]-3-cyclopentylpropanamide Chemical compound FC(F)(F)C1=CC(N2CCOCC2)=CC(Br)=C1NC(=O)CCC1CCCC1 LNEODKACMQDIAF-UHFFFAOYSA-N 0.000 claims description 2
- AOSDPVXNYCUYSW-UHFFFAOYSA-N n-[2-chloro-4-[(3,4-dichloroanilino)methyl]phenyl]butanamide Chemical compound C1=C(Cl)C(NC(=O)CCC)=CC=C1CNC1=CC=C(Cl)C(Cl)=C1 AOSDPVXNYCUYSW-UHFFFAOYSA-N 0.000 claims description 2
- HSXJTDIWKDHOPI-UHFFFAOYSA-N n-[2-chloro-4-[(3-fluoroanilino)methyl]phenyl]butanamide Chemical compound C1=C(Cl)C(NC(=O)CCC)=CC=C1CNC1=CC=CC(F)=C1 HSXJTDIWKDHOPI-UHFFFAOYSA-N 0.000 claims description 2
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- SHXIJKYXFWJGDT-UHFFFAOYSA-N n-[2-chloro-4-[(4-chloroanilino)methyl]phenyl]butanamide Chemical compound C1=C(Cl)C(NC(=O)CCC)=CC=C1CNC1=CC=C(Cl)C=C1 SHXIJKYXFWJGDT-UHFFFAOYSA-N 0.000 claims description 2
- HRQLXROTHVOVME-UHFFFAOYSA-N n-[2-chloro-4-[(4-fluoroanilino)methyl]phenyl]butanamide Chemical compound C1=C(Cl)C(NC(=O)CCC)=CC=C1CNC1=CC=C(F)C=C1 HRQLXROTHVOVME-UHFFFAOYSA-N 0.000 claims description 2
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- ZXIJIODJNIISBC-UHFFFAOYSA-N n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]butanamide Chemical compound C1=C(Cl)C(NC(=O)CCC)=CC=C1N(C)CC1=CC=C(Cl)S1 ZXIJIODJNIISBC-UHFFFAOYSA-N 0.000 claims description 2
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- XFXDQNZGCOJIKK-UHFFFAOYSA-N n-[6-amino-1-[(5-chlorothiophen-2-yl)methyl]-2,3-dihydroindol-5-yl]-2,2-dimethylpropanamide Chemical compound C1=2C=C(N)C(NC(=O)C(C)(C)C)=CC=2CCN1CC1=CC=C(Cl)S1 XFXDQNZGCOJIKK-UHFFFAOYSA-N 0.000 claims description 2
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- PFXGSJZQUMCENI-UHFFFAOYSA-N n-[6-amino-1-[[3-fluoro-4-(trifluoromethyl)phenyl]methyl]-2,3-dihydroindol-5-yl]-3,3-dimethylbutanamide Chemical compound C1=2C=C(N)C(NC(=O)CC(C)(C)C)=CC=2CCN1CC1=CC=C(C(F)(F)F)C(F)=C1 PFXGSJZQUMCENI-UHFFFAOYSA-N 0.000 claims description 2
- BDNMQAIDXMFIPX-UHFFFAOYSA-N n-[6-amino-1-[[4-(trifluoromethyl)phenyl]methyl]-2,3-dihydroindol-5-yl]-2,2-dimethylpropanamide Chemical compound C1=2C=C(N)C(NC(=O)C(C)(C)C)=CC=2CCN1CC1=CC=C(C(F)(F)F)C=C1 BDNMQAIDXMFIPX-UHFFFAOYSA-N 0.000 claims description 2
- LEAGGTMYQUKNJZ-UHFFFAOYSA-N n-[6-amino-1-[[4-(trifluoromethyl)phenyl]methyl]-2,3-dihydroindol-5-yl]-2-(4-fluorophenyl)acetamide Chemical compound C1CC=2C=C(NC(=O)CC=3C=CC(F)=CC=3)C(N)=CC=2N1CC1=CC=C(C(F)(F)F)C=C1 LEAGGTMYQUKNJZ-UHFFFAOYSA-N 0.000 claims description 2
- IAZYLAOKVSTMMF-UHFFFAOYSA-N n-[6-amino-1-[[4-(trifluoromethyl)phenyl]methyl]-2,3-dihydroindol-5-yl]-3,3-dimethylbutanamide Chemical compound C1=2C=C(N)C(NC(=O)CC(C)(C)C)=CC=2CCN1CC1=CC=C(C(F)(F)F)C=C1 IAZYLAOKVSTMMF-UHFFFAOYSA-N 0.000 claims description 2
- SJZUZZGCSNZQTD-UHFFFAOYSA-N n-[6-bromo-1-[(5-chlorothiophen-2-yl)methyl]-2,3-dihydroindol-5-yl]-3,3-dimethylbutanamide Chemical compound C1=2C=C(Br)C(NC(=O)CC(C)(C)C)=CC=2CCN1CC1=CC=C(Cl)S1 SJZUZZGCSNZQTD-UHFFFAOYSA-N 0.000 claims description 2
- ZAXBJTRAIGCMSW-UHFFFAOYSA-N n-[6-bromo-1-[[4-(trifluoromethyl)phenyl]methyl]-2,3-dihydroindol-5-yl]-3,3-dimethylbutanamide Chemical compound C1=2C=C(Br)C(NC(=O)CC(C)(C)C)=CC=2CCN1CC1=CC=C(C(F)(F)F)C=C1 ZAXBJTRAIGCMSW-UHFFFAOYSA-N 0.000 claims description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 2
- 230000002085 persistent effect Effects 0.000 claims description 2
- QYNJALBPNQXKOG-UHFFFAOYSA-N phenyl n-[2-chloro-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]carbamate Chemical compound C=1C=C(NC(=O)OC=2C=CC=CC=2)C(Cl)=CC=1N(C)CC1=CC=C(Cl)S1 QYNJALBPNQXKOG-UHFFFAOYSA-N 0.000 claims description 2
- MXUJFQOMTXBKEL-UHFFFAOYSA-N propan-2-yl n-[4-[(5-bromothiophen-2-yl)methylamino]-2-methoxyphenyl]carbamate Chemical compound C1=C(NC(=O)OC(C)C)C(OC)=CC(NCC=2SC(Br)=CC=2)=C1 MXUJFQOMTXBKEL-UHFFFAOYSA-N 0.000 claims description 2
- AQMMAJZBLIFENA-UHFFFAOYSA-N propyl n-(4-bromo-2,6-dimethylphenyl)carbamate Chemical compound CCCOC(=O)NC1=C(C)C=C(Br)C=C1C AQMMAJZBLIFENA-UHFFFAOYSA-N 0.000 claims description 2
- SIMHCLCXJNWNEF-UHFFFAOYSA-N propyl n-[1-[(4-fluorophenyl)methyl]-2,3-dihydroindol-5-yl]carbamate Chemical compound C1CC2=CC(NC(=O)OCCC)=CC=C2N1CC1=CC=C(F)C=C1 SIMHCLCXJNWNEF-UHFFFAOYSA-N 0.000 claims description 2
- PRTLUEMAYPPJKC-UHFFFAOYSA-N propyl n-[1-[(5-chlorothiophen-2-yl)methyl]-2,3-dihydroindol-5-yl]carbamate Chemical compound C1CC2=CC(NC(=O)OCCC)=CC=C2N1CC1=CC=C(Cl)S1 PRTLUEMAYPPJKC-UHFFFAOYSA-N 0.000 claims description 2
- YVNQJVUAEHJVSD-UHFFFAOYSA-N propyl n-[2,6-dimethyl-4-[(4-methyl-2-phenylpyrimidin-5-yl)methylamino]phenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCCC)=C(C)C=C1NCC1=CN=C(C=2C=CC=CC=2)N=C1C YVNQJVUAEHJVSD-UHFFFAOYSA-N 0.000 claims description 2
- SCZBYOLAIVJLAL-UHFFFAOYSA-N propyl n-[2,6-dimethyl-4-[[4-(trifluoromethyl)anilino]methyl]phenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCCC)=C(C)C=C1CNC1=CC=C(C(F)(F)F)C=C1 SCZBYOLAIVJLAL-UHFFFAOYSA-N 0.000 claims description 2
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- KAMAAAVPELJCKX-UHFFFAOYSA-N propyl n-[2,6-dimethyl-4-[[6-(4-methylphenoxy)pyridin-3-yl]methylamino]phenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCCC)=C(C)C=C1NCC(C=N1)=CC=C1OC1=CC=C(C)C=C1 KAMAAAVPELJCKX-UHFFFAOYSA-N 0.000 claims description 2
- GUWWVMJPRYOTKR-UHFFFAOYSA-N propyl n-[2-(furan-2-yl)-4-[(4-propan-2-ylphenyl)methylamino]phenyl]carbamate Chemical compound C1=C(C=2OC=CC=2)C(NC(=O)OCCC)=CC=C1NCC1=CC=C(C(C)C)C=C1 GUWWVMJPRYOTKR-UHFFFAOYSA-N 0.000 claims description 2
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- KYYUTTNFUCOPCS-UHFFFAOYSA-N propyl n-[2-amino-4-(1-benzothiophen-2-ylmethylamino)phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCCC)=CC=C1NCC1=CC2=CC=CC=C2S1 KYYUTTNFUCOPCS-UHFFFAOYSA-N 0.000 claims description 2
- NHFRVRNKRNDFPO-UHFFFAOYSA-N propyl n-[2-amino-4-(1-benzothiophen-3-ylmethylamino)phenyl]carbamate Chemical compound C1=C(N)C(NC(=O)OCCC)=CC=C1NCC1=CSC2=CC=CC=C12 NHFRVRNKRNDFPO-UHFFFAOYSA-N 0.000 claims description 2
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- RFBPNVJIXZBIRC-UHFFFAOYSA-N propyl n-[2-bromo-4-[(5-chlorothiophen-2-yl)methyl-methylamino]phenyl]carbamate Chemical compound C1=C(Br)C(NC(=O)OCCC)=CC=C1N(C)CC1=CC=C(Cl)S1 RFBPNVJIXZBIRC-UHFFFAOYSA-N 0.000 claims description 2
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- FJOCXCMSKXJZSK-UHFFFAOYSA-N propyl n-[2-bromo-4-[methyl-[(4-propan-2-ylphenyl)methyl]amino]phenyl]carbamate Chemical compound C1=C(Br)C(NC(=O)OCCC)=CC=C1N(C)CC1=CC=C(C(C)C)C=C1 FJOCXCMSKXJZSK-UHFFFAOYSA-N 0.000 claims description 2
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- AFEGKGPOQWHFQJ-UHFFFAOYSA-N propyl n-[2-chloro-4-[(5-chlorothiophen-2-yl)methylamino]phenyl]carbamate Chemical compound C1=C(Cl)C(NC(=O)OCCC)=CC=C1NCC1=CC=C(Cl)S1 AFEGKGPOQWHFQJ-UHFFFAOYSA-N 0.000 claims description 2
- UGBFSKGLWGZLCW-UHFFFAOYSA-N propyl n-[2-chloro-4-[(5-methylthiophen-2-yl)methylamino]phenyl]carbamate Chemical compound C1=C(Cl)C(NC(=O)OCCC)=CC=C1NCC1=CC=C(C)S1 UGBFSKGLWGZLCW-UHFFFAOYSA-N 0.000 claims description 2
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- HMQPLANFTAPTBN-UHFFFAOYSA-N propyl n-[2-cyano-4-[[4-(trifluoromethyl)phenyl]methylamino]phenyl]carbamate Chemical compound C1=C(C#N)C(NC(=O)OCCC)=CC=C1NCC1=CC=C(C(F)(F)F)C=C1 HMQPLANFTAPTBN-UHFFFAOYSA-N 0.000 claims description 2
- QMKMMGGJLUWMDT-UHFFFAOYSA-N propyl n-[2-iodo-4-[(4-methylsulfanylphenyl)methylamino]phenyl]carbamate Chemical compound C1=C(I)C(NC(=O)OCCC)=CC=C1NCC1=CC=C(SC)C=C1 QMKMMGGJLUWMDT-UHFFFAOYSA-N 0.000 claims description 2
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- BHLLLFQNDMQXGM-UHFFFAOYSA-N propyl n-[4-[(4-methoxyanilino)methyl]-2,6-dimethylphenyl]carbamate Chemical compound C1=C(C)C(NC(=O)OCCC)=C(C)C=C1CNC1=CC=C(OC)C=C1 BHLLLFQNDMQXGM-UHFFFAOYSA-N 0.000 claims description 2
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| US95330807P | 2007-08-01 | 2007-08-01 | |
| DKPA200701110 | 2007-08-01 | ||
| PCT/DK2008/050191 WO2009015667A1 (en) | 2007-08-01 | 2008-07-31 | Use of kncq potassium channel openers for reducing symptoms of or treating disorders or conditions wherein the dopaminergic system is disrupted |
Publications (2)
| Publication Number | Publication Date |
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| JP2011513196A true JP2011513196A (ja) | 2011-04-28 |
| JP2011513196A5 JP2011513196A5 (OSRAM) | 2011-07-21 |
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Family Applications (1)
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| JP2010518498A Ceased JP2011513196A (ja) | 2007-08-01 | 2008-07-31 | ドーパミン作動系が破壊された障害もしくは状態の症状を軽減するためまたはその障害もしくは状態を処置するためのkcnqカリウムチャネル開口薬の使用 |
Country Status (17)
| Country | Link |
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| US (1) | US20100256145A1 (OSRAM) |
| EP (1) | EP2185149A1 (OSRAM) |
| JP (1) | JP2011513196A (OSRAM) |
| KR (1) | KR20100050502A (OSRAM) |
| CN (1) | CN101790374A (OSRAM) |
| AR (1) | AR070513A1 (OSRAM) |
| AU (1) | AU2008281112A1 (OSRAM) |
| BR (1) | BRPI0814180A2 (OSRAM) |
| CA (1) | CA2694887A1 (OSRAM) |
| CL (1) | CL2008002273A1 (OSRAM) |
| EA (1) | EA201070189A1 (OSRAM) |
| MX (1) | MX2010001171A (OSRAM) |
| NZ (1) | NZ582942A (OSRAM) |
| TW (1) | TW200920350A (OSRAM) |
| UA (1) | UA97847C2 (OSRAM) |
| WO (1) | WO2009015667A1 (OSRAM) |
| ZA (1) | ZA201000129B (OSRAM) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016540051A (ja) * | 2013-12-02 | 2016-12-22 | ケモセントリックス,インコーポレイティド | Ccr6化合物 |
| JP2018048143A (ja) * | 2014-10-24 | 2018-03-29 | 小野薬品工業株式会社 | Kcnq2〜5チャネル活性化剤 |
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016540051A (ja) * | 2013-12-02 | 2016-12-22 | ケモセントリックス,インコーポレイティド | Ccr6化合物 |
| US10786494B2 (en) | 2013-12-02 | 2020-09-29 | Chemocentryx, Inc. | CCR6 compounds |
| JP2018048143A (ja) * | 2014-10-24 | 2018-03-29 | 小野薬品工業株式会社 | Kcnq2〜5チャネル活性化剤 |
| US10676438B2 (en) | 2014-10-24 | 2020-06-09 | Ono Pharmaceutical Co., Ltd. | KCNQ2-5 channel activator |
| JP2019518754A (ja) * | 2016-06-10 | 2019-07-04 | サイフルーア ライフ サイエンシズ インコーポレイテッド | フッ素化2−アミノ−4−(置換アミノ)フェニルカルバメート誘導体 |
| JP2021525241A (ja) * | 2018-05-22 | 2021-09-24 | シャンハイ ジムン バイオファーマ, インコーポレーテッドShanghai Zhimeng Biopharma Inc. | カリウムチャネル調節剤としてのp−ジアミノベンゼン誘導体、その製造方法およびその医薬における使用 |
| JP7294681B2 (ja) | 2018-05-22 | 2023-06-20 | シャンハイ ジムン バイオファーマ,インコーポレーテッド | カリウムチャネル調節剤としてのp-ジアミノベンゼン誘導体、その製造方法およびその医薬における使用 |
| JP2022553569A (ja) * | 2019-11-08 | 2022-12-23 | ゼノン・ファーマシューティカルズ・インコーポレイテッド | うつ病性障害の治療方法 |
| JP2025504538A (ja) * | 2022-01-25 | 2025-02-12 | シャンハイ ジムン バイオファーマ,インコーポレーテッド | カリウムチャネル調節剤としてのアミド系化合物およびその製造と使用 |
Also Published As
| Publication number | Publication date |
|---|---|
| BRPI0814180A2 (pt) | 2015-01-27 |
| AU2008281112A1 (en) | 2009-02-05 |
| TW200920350A (en) | 2009-05-16 |
| WO2009015667A1 (en) | 2009-02-05 |
| CA2694887A1 (en) | 2009-02-05 |
| US20100256145A1 (en) | 2010-10-07 |
| MX2010001171A (es) | 2010-03-01 |
| CN101790374A (zh) | 2010-07-28 |
| ZA201000129B (en) | 2011-04-28 |
| UA97847C2 (ru) | 2012-03-26 |
| KR20100050502A (ko) | 2010-05-13 |
| EP2185149A1 (en) | 2010-05-19 |
| EA201070189A1 (ru) | 2010-08-30 |
| NZ582942A (en) | 2011-09-30 |
| CL2008002273A1 (es) | 2009-07-17 |
| AR070513A1 (es) | 2010-04-14 |
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