JP2013538801A5 - - Google Patents
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- JP2013538801A5 JP2013538801A5 JP2013523639A JP2013523639A JP2013538801A5 JP 2013538801 A5 JP2013538801 A5 JP 2013538801A5 JP 2013523639 A JP2013523639 A JP 2013523639A JP 2013523639 A JP2013523639 A JP 2013523639A JP 2013538801 A5 JP2013538801 A5 JP 2013538801A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- dihydro
- inden
- azetidin
- benzyl
- 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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- 229910052739 hydrogen Inorganic materials 0.000 claims 29
- 239000001257 hydrogen Substances 0.000 claims 29
- 150000001875 compounds Chemical class 0.000 claims 20
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 12
- 150000002431 hydrogen Chemical class 0.000 claims 11
- -1 2- (azetidin-1-yl) -3-benzyl-2,3-dihydro-1H-inden-5-yl Chemical group 0.000 claims 8
- 125000002947 alkylene group Chemical group 0.000 claims 7
- 150000001408 amides Chemical class 0.000 claims 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 4
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 4
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims 4
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims 4
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 3
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 3
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims 2
- FOCROFGIBCODPQ-UHFFFAOYSA-N 6-[1-(cyclopropylmethylsulfonyl)azetidin-3-yl]-5-fluoro-n-methyl-1-[[3-(trifluoromethyl)phenyl]methyl]-2,3-dihydro-1h-inden-2-amine Chemical compound CNC1CC2=CC(F)=C(C3CN(C3)S(=O)(=O)CC3CC3)C=C2C1CC1=CC=CC(C(F)(F)F)=C1 FOCROFGIBCODPQ-UHFFFAOYSA-N 0.000 claims 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
- HYMXQESPSIAYCN-UHFFFAOYSA-N cyclobutanesulfonamide Chemical compound NS(=O)(=O)C1CCC1 HYMXQESPSIAYCN-UHFFFAOYSA-N 0.000 claims 2
- FFPMOSGZHPLKRI-UHFFFAOYSA-N n-[2-[(2-amino-3-benzyl-2,3-dihydro-1h-inden-5-yl)oxy]ethyl]-1-methylimidazole-4-sulfonamide Chemical compound CN1C=NC(S(=O)(=O)NCCOC=2C=C3C(CC=4C=CC=CC=4)C(N)CC3=CC=2)=C1 FFPMOSGZHPLKRI-UHFFFAOYSA-N 0.000 claims 2
- AYLMICVUEAJFFO-UHFFFAOYSA-N n-[2-[[2-(azetidin-1-yl)-3-benzyl-2,3-dihydro-1h-inden-5-yl]oxy]ethyl]-1-methylimidazole-4-sulfonamide Chemical compound CN1C=NC(S(=O)(=O)NCCOC=2C=C3C(CC=4C=CC=CC=4)C(CC3=CC=2)N2CCC2)=C1 AYLMICVUEAJFFO-UHFFFAOYSA-N 0.000 claims 2
- ASMWJUHBWHAICQ-UHFFFAOYSA-N n-[2-[[3-benzyl-2-(methylamino)-2,3-dihydro-1h-inden-5-yl]oxy]ethyl]-1-methylimidazole-4-sulfonamide Chemical compound C1=C2C(CC=3C=CC=CC=3)C(NC)CC2=CC=C1OCCNS(=O)(=O)C1=CN(C)C=N1 ASMWJUHBWHAICQ-UHFFFAOYSA-N 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 2
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 2
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 1
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
- SEPPVOUBHWNCAW-FNORWQNLSA-N (E)-4-oxonon-2-enal Chemical compound CCCCCC(=O)\C=C\C=O SEPPVOUBHWNCAW-FNORWQNLSA-N 0.000 claims 1
- YCFSVEDNLBHDEC-UHFFFAOYSA-N 1-[(3-chlorophenyl)methyl]-5-fluoro-n-methyl-6-[1-(1-methylpyrazol-4-yl)sulfonylazetidin-3-yl]-2,3-dihydro-1h-inden-2-amine Chemical compound CNC1CC2=CC(F)=C(C3CN(C3)S(=O)(=O)C3=CN(C)N=C3)C=C2C1CC1=CC=CC(Cl)=C1 YCFSVEDNLBHDEC-UHFFFAOYSA-N 0.000 claims 1
- GYZLLGIOIVPJSJ-UHFFFAOYSA-N 1-[(3-chlorophenyl)methyl]-6-(1-cyclobutylsulfonylazetidin-3-yl)-5-fluoro-n-methyl-2,3-dihydro-1h-inden-2-amine Chemical compound CNC1CC2=CC(F)=C(C3CN(C3)S(=O)(=O)C3CCC3)C=C2C1CC1=CC=CC(Cl)=C1 GYZLLGIOIVPJSJ-UHFFFAOYSA-N 0.000 claims 1
- CLNULLRTGHUVFQ-UHFFFAOYSA-N 1-[(3-chlorophenyl)methyl]-6-(1-cyclobutylsulfonylazetidin-3-yl)-n-methyl-2,3-dihydro-1h-inden-2-amine Chemical compound CNC1CC2=CC=C(C3CN(C3)S(=O)(=O)C3CCC3)C=C2C1CC1=CC=CC(Cl)=C1 CLNULLRTGHUVFQ-UHFFFAOYSA-N 0.000 claims 1
- SVCBTNDKARTAHK-UHFFFAOYSA-N 1-[(3-chlorophenyl)methyl]-6-[1-(cyclopropylmethylsulfonyl)azetidin-3-yl]-5-fluoro-n-methyl-2,3-dihydro-1h-inden-2-amine Chemical compound CNC1CC2=CC(F)=C(C3CN(C3)S(=O)(=O)CC3CC3)C=C2C1CC1=CC=CC(Cl)=C1 SVCBTNDKARTAHK-UHFFFAOYSA-N 0.000 claims 1
- GNQGWALOCPNURM-UHFFFAOYSA-N 1-[(3-chlorophenyl)methyl]-6-[1-(cyclopropylmethylsulfonyl)azetidin-3-yl]-n-methyl-2,3-dihydro-1h-inden-2-amine Chemical compound CNC1CC2=CC=C(C3CN(C3)S(=O)(=O)CC3CC3)C=C2C1CC1=CC=CC(Cl)=C1 GNQGWALOCPNURM-UHFFFAOYSA-N 0.000 claims 1
- ICOSTTFPPNACCZ-UHFFFAOYSA-N 1-[(3-chlorophenyl)methyl]-n-methyl-6-[1-(1-methylimidazol-4-yl)sulfonylazetidin-3-yl]-2,3-dihydro-1h-inden-2-amine Chemical compound CNC1CC2=CC=C(C3CN(C3)S(=O)(=O)C=3N=CN(C)C=3)C=C2C1CC1=CC=CC(Cl)=C1 ICOSTTFPPNACCZ-UHFFFAOYSA-N 0.000 claims 1
- AVPCOALMQYAREH-UHFFFAOYSA-N 1-[(3-chlorophenyl)methyl]-n-methyl-6-[1-(1-methylpyrazol-4-yl)sulfonylazetidin-3-yl]-2,3-dihydro-1h-inden-2-amine Chemical compound CNC1CC2=CC=C(C3CN(C3)S(=O)(=O)C3=CN(C)N=C3)C=C2C1CC1=CC=CC(Cl)=C1 AVPCOALMQYAREH-UHFFFAOYSA-N 0.000 claims 1
- NPHHZLVFRPCFMX-UHFFFAOYSA-N 1-[(3-fluorophenyl)methyl]-n-methyl-6-[1-(1-methylimidazol-4-yl)sulfonylazetidin-3-yl]-2,3-dihydro-1h-inden-2-amine Chemical compound CNC1CC2=CC=C(C3CN(C3)S(=O)(=O)C=3N=CN(C)C=3)C=C2C1CC1=CC=CC(F)=C1 NPHHZLVFRPCFMX-UHFFFAOYSA-N 0.000 claims 1
- IOADGRSVYKWWAP-UHFFFAOYSA-N 1-[(3-fluorophenyl)methyl]-n-methyl-6-[1-(1-methylpyrazol-4-yl)sulfonylazetidin-3-yl]-2,3-dihydro-1h-inden-2-amine Chemical compound CNC1CC2=CC=C(C3CN(C3)S(=O)(=O)C3=CN(C)N=C3)C=C2C1CC1=CC=CC(F)=C1 IOADGRSVYKWWAP-UHFFFAOYSA-N 0.000 claims 1
- ORARWOCMUSIWGV-UHFFFAOYSA-N 1-benzyl-5-fluoro-n-methyl-6-[1-(1-methylimidazol-4-yl)sulfonylazetidin-3-yl]-2,3-dihydro-1h-inden-2-amine Chemical compound CNC1CC2=CC(F)=C(C3CN(C3)S(=O)(=O)C=3N=CN(C)C=3)C=C2C1CC1=CC=CC=C1 ORARWOCMUSIWGV-UHFFFAOYSA-N 0.000 claims 1
- BUSGITHBTCXMKA-UHFFFAOYSA-N 1-benzyl-5-fluoro-n-methyl-6-[1-(1-methylpyrazol-4-yl)sulfonylazetidin-3-yl]-2,3-dihydro-1h-inden-2-amine Chemical compound CNC1CC2=CC(F)=C(C3CN(C3)S(=O)(=O)C3=CN(C)N=C3)C=C2C1CC1=CC=CC=C1 BUSGITHBTCXMKA-UHFFFAOYSA-N 0.000 claims 1
- PDAZXIWPZRACPB-UHFFFAOYSA-N 1-benzyl-6-(1-cyclobutylsulfonylazetidin-3-yl)-5-fluoro-n-methyl-2,3-dihydro-1h-inden-2-amine Chemical compound CNC1CC2=CC(F)=C(C3CN(C3)S(=O)(=O)C3CCC3)C=C2C1CC1=CC=CC=C1 PDAZXIWPZRACPB-UHFFFAOYSA-N 0.000 claims 1
- MECVMBPYTNCIGP-UHFFFAOYSA-N 1-benzyl-6-(1-cyclobutylsulfonylazetidin-3-yl)-n-methyl-2,3-dihydro-1h-inden-2-amine Chemical compound CNC1CC2=CC=C(C3CN(C3)S(=O)(=O)C3CCC3)C=C2C1CC1=CC=CC=C1 MECVMBPYTNCIGP-UHFFFAOYSA-N 0.000 claims 1
- ODBKWHOOTRVKQD-UHFFFAOYSA-N 1-benzyl-6-[1-(cyclopropylmethylsulfonyl)azetidin-3-yl]-5-fluoro-n-methyl-2,3-dihydro-1h-inden-2-amine Chemical compound CNC1CC2=CC(F)=C(C3CN(C3)S(=O)(=O)CC3CC3)C=C2C1CC1=CC=CC=C1 ODBKWHOOTRVKQD-UHFFFAOYSA-N 0.000 claims 1
- KTONZGOCTKWQRD-UHFFFAOYSA-N 1-benzyl-6-[1-(cyclopropylmethylsulfonyl)azetidin-3-yl]-n-methyl-2,3-dihydro-1h-inden-2-amine Chemical compound CNC1CC2=CC=C(C3CN(C3)S(=O)(=O)CC3CC3)C=C2C1CC1=CC=CC=C1 KTONZGOCTKWQRD-UHFFFAOYSA-N 0.000 claims 1
- NFPXIBMEXFVHRB-UHFFFAOYSA-N 1-benzyl-n-methyl-6-[1-(1-methylimidazol-4-yl)sulfonylazetidin-3-yl]-2,3-dihydro-1h-inden-2-amine Chemical compound CNC1CC2=CC=C(C3CN(C3)S(=O)(=O)C=3N=CN(C)C=3)C=C2C1CC1=CC=CC=C1 NFPXIBMEXFVHRB-UHFFFAOYSA-N 0.000 claims 1
- PNAYWJNMSDMMFD-UHFFFAOYSA-N 1-benzyl-n-methyl-6-[1-(1-methylpyrazol-4-yl)sulfonylazetidin-3-yl]-2,3-dihydro-1h-inden-2-amine Chemical compound CNC1CC2=CC=C(C3CN(C3)S(=O)(=O)C3=CN(C)N=C3)C=C2C1CC1=CC=CC=C1 PNAYWJNMSDMMFD-UHFFFAOYSA-N 0.000 claims 1
- MUSFFHRFNIWSLK-UHFFFAOYSA-N 1-methyl-n-[2-[[2-(methylamino)-3-[[3-(trifluoromethyl)phenyl]methyl]-2,3-dihydro-1h-inden-5-yl]oxy]ethyl]imidazole-4-sulfonamide Chemical compound C1=C2C(CC=3C=C(C=CC=3)C(F)(F)F)C(NC)CC2=CC=C1OCCNS(=O)(=O)C1=CN(C)C=N1 MUSFFHRFNIWSLK-UHFFFAOYSA-N 0.000 claims 1
- IXKBDFRBOLOLQP-UHFFFAOYSA-N 1-methyl-n-[2-[[2-(methylamino)-3-[[3-(trifluoromethyl)phenyl]methyl]-2,3-dihydro-1h-inden-5-yl]oxy]ethyl]pyrazole-4-sulfonamide Chemical compound C1=C2C(CC=3C=C(C=CC=3)C(F)(F)F)C(NC)CC2=CC=C1OCCNS(=O)(=O)C=1C=NN(C)C=1 IXKBDFRBOLOLQP-UHFFFAOYSA-N 0.000 claims 1
- DVFVMELGAUSHNL-UHFFFAOYSA-N 1-methyl-n-[[2-(methylamino)-3-[[3-(trifluoromethyl)phenyl]methyl]-2,3-dihydro-1h-inden-5-yl]methyl]imidazole-4-sulfonamide Chemical compound C1=C2C(CC=3C=C(C=CC=3)C(F)(F)F)C(NC)CC2=CC=C1CNS(=O)(=O)C1=CN(C)C=N1 DVFVMELGAUSHNL-UHFFFAOYSA-N 0.000 claims 1
- DVCKEUATPVJFFB-UHFFFAOYSA-N 1-methyl-n-[[2-(methylamino)-3-[[3-(trifluoromethyl)phenyl]methyl]-2,3-dihydro-1h-inden-5-yl]methyl]pyrazole-4-sulfonamide Chemical compound C1=C2C(CC=3C=C(C=CC=3)C(F)(F)F)C(NC)CC2=CC=C1CNS(=O)(=O)C=1C=NN(C)C=1 DVCKEUATPVJFFB-UHFFFAOYSA-N 0.000 claims 1
- QBJSSOBNVYDCDQ-UHFFFAOYSA-N 1-methylimidazole-4-sulfonamide Chemical compound CN1C=NC(S(N)(=O)=O)=C1 QBJSSOBNVYDCDQ-UHFFFAOYSA-N 0.000 claims 1
- XJEVHMGJSYVQBQ-UHFFFAOYSA-N 2,3-dihydro-1h-inden-1-amine Chemical class C1=CC=C2C(N)CCC2=C1 XJEVHMGJSYVQBQ-UHFFFAOYSA-N 0.000 claims 1
- DJVDUWXJMWPBGM-UHFFFAOYSA-N 3-[2-(azetidin-1-yl)-3-[(3-chlorophenyl)methyl]-2,3-dihydro-1h-inden-5-yl]-1-(cyclopropylmethylsulfonyl)azetidine Chemical compound ClC1=CC=CC(CC2C3=CC(=CC=C3CC2N2CCC2)C2CN(C2)S(=O)(=O)CC2CC2)=C1 DJVDUWXJMWPBGM-UHFFFAOYSA-N 0.000 claims 1
- OMQCBIGXJAFNSU-UHFFFAOYSA-N 3-[2-(azetidin-1-yl)-3-[(3-chlorophenyl)methyl]-2,3-dihydro-1h-inden-5-yl]-1-cyclobutylsulfonylazetidine Chemical compound ClC1=CC=CC(CC2C3=CC(=CC=C3CC2N2CCC2)C2CN(C2)S(=O)(=O)C2CCC2)=C1 OMQCBIGXJAFNSU-UHFFFAOYSA-N 0.000 claims 1
- VSGAPWIHSSXRIM-UHFFFAOYSA-N 3-[2-(azetidin-1-yl)-3-[(3-chlorophenyl)methyl]-6-fluoro-2,3-dihydro-1h-inden-5-yl]-1-(cyclopropylmethylsulfonyl)azetidine Chemical compound C1=2C=C(C3CN(C3)S(=O)(=O)CC3CC3)C(F)=CC=2CC(N2CCC2)C1CC1=CC=CC(Cl)=C1 VSGAPWIHSSXRIM-UHFFFAOYSA-N 0.000 claims 1
- XINIVAUEFYXUEF-UHFFFAOYSA-N 3-[2-(azetidin-1-yl)-3-[(3-chlorophenyl)methyl]-6-fluoro-2,3-dihydro-1h-inden-5-yl]-1-cyclobutylsulfonylazetidine Chemical compound C1=2C=C(C3CN(C3)S(=O)(=O)C3CCC3)C(F)=CC=2CC(N2CCC2)C1CC1=CC=CC(Cl)=C1 XINIVAUEFYXUEF-UHFFFAOYSA-N 0.000 claims 1
- DYMWWSDVHRDKDE-UHFFFAOYSA-N 3-[2-(azetidin-1-yl)-3-[(3-fluorophenyl)methyl]-2,3-dihydro-1h-inden-5-yl]-1-(cyclopropylmethylsulfonyl)azetidine Chemical compound FC1=CC=CC(CC2C3=CC(=CC=C3CC2N2CCC2)C2CN(C2)S(=O)(=O)CC2CC2)=C1 DYMWWSDVHRDKDE-UHFFFAOYSA-N 0.000 claims 1
- LDQVLEPMPQEMAY-UHFFFAOYSA-N 3-[2-(azetidin-1-yl)-3-[(3-fluorophenyl)methyl]-2,3-dihydro-1h-inden-5-yl]-1-cyclobutylsulfonylazetidine Chemical compound FC1=CC=CC(CC2C3=CC(=CC=C3CC2N2CCC2)C2CN(C2)S(=O)(=O)C2CCC2)=C1 LDQVLEPMPQEMAY-UHFFFAOYSA-N 0.000 claims 1
- ADYIUFRQVJNBDE-UHFFFAOYSA-N 3-[2-(azetidin-1-yl)-3-benzyl-2,3-dihydro-1h-inden-5-yl]-1-(cyclopropylmethylsulfonyl)azetidine Chemical compound C1C(C=2C=C3C(CC=4C=CC=CC=4)C(CC3=CC=2)N2CCC2)CN1S(=O)(=O)CC1CC1 ADYIUFRQVJNBDE-UHFFFAOYSA-N 0.000 claims 1
- PLFFGEKUKRKUSP-UHFFFAOYSA-N 3-[2-(azetidin-1-yl)-3-benzyl-6-fluoro-2,3-dihydro-1h-inden-5-yl]-1-(cyclopropylmethylsulfonyl)azetidine Chemical compound C1=2C=C(C3CN(C3)S(=O)(=O)CC3CC3)C(F)=CC=2CC(N2CCC2)C1CC1=CC=CC=C1 PLFFGEKUKRKUSP-UHFFFAOYSA-N 0.000 claims 1
- CSESFPDVNUVKBD-UHFFFAOYSA-N 3-[2-(azetidin-1-yl)-3-benzyl-6-fluoro-2,3-dihydro-1h-inden-5-yl]-1-cyclobutylsulfonylazetidine Chemical compound C1=2C=C(C3CN(C3)S(=O)(=O)C3CCC3)C(F)=CC=2CC(N2CCC2)C1CC1=CC=CC=C1 CSESFPDVNUVKBD-UHFFFAOYSA-N 0.000 claims 1
- CMGDONCUDBJFJG-UHFFFAOYSA-N 3-[2-(azetidin-1-yl)-6-fluoro-3-[(3-fluorophenyl)methyl]-2,3-dihydro-1h-inden-5-yl]-1-(cyclopropylmethylsulfonyl)azetidine Chemical compound FC1=CC=CC(CC2C3=CC(=C(F)C=C3CC2N2CCC2)C2CN(C2)S(=O)(=O)CC2CC2)=C1 CMGDONCUDBJFJG-UHFFFAOYSA-N 0.000 claims 1
- PXEJIHIACOWOHB-UHFFFAOYSA-N 3-[2-(azetidin-1-yl)-6-fluoro-3-[(3-fluorophenyl)methyl]-2,3-dihydro-1h-inden-5-yl]-1-cyclobutylsulfonylazetidine Chemical compound FC1=CC=CC(CC2C3=CC(=C(F)C=C3CC2N2CCC2)C2CN(C2)S(=O)(=O)C2CCC2)=C1 PXEJIHIACOWOHB-UHFFFAOYSA-N 0.000 claims 1
- FKGDRTCZXOXTPH-UHFFFAOYSA-N 3-[2-(azetidin-1-yl)-6-fluoro-3-[[3-(trifluoromethyl)phenyl]methyl]-2,3-dihydro-1h-inden-5-yl]-1-(cyclopropylmethylsulfonyl)azetidine Chemical compound C1=2C=C(C3CN(C3)S(=O)(=O)CC3CC3)C(F)=CC=2CC(N2CCC2)C1CC1=CC=CC(C(F)(F)F)=C1 FKGDRTCZXOXTPH-UHFFFAOYSA-N 0.000 claims 1
- AACWJSRYRUJLLJ-UHFFFAOYSA-N 3-[2-(azetidin-1-yl)-6-fluoro-3-[[3-(trifluoromethyl)phenyl]methyl]-2,3-dihydro-1h-inden-5-yl]-1-cyclobutylsulfonylazetidine Chemical compound C1=2C=C(C3CN(C3)S(=O)(=O)C3CCC3)C(F)=CC=2CC(N2CCC2)C1CC1=CC=CC(C(F)(F)F)=C1 AACWJSRYRUJLLJ-UHFFFAOYSA-N 0.000 claims 1
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims 1
- OUSVOKHHQADVBW-UHFFFAOYSA-N 4-[3-[2-(azetidin-1-yl)-3-[(3-chlorophenyl)methyl]-2,3-dihydro-1h-inden-5-yl]azetidin-1-yl]sulfonyl-1-methylimidazole Chemical compound CN1C=NC(S(=O)(=O)N2CC(C2)C=2C=C3C(CC=4C=C(Cl)C=CC=4)C(CC3=CC=2)N2CCC2)=C1 OUSVOKHHQADVBW-UHFFFAOYSA-N 0.000 claims 1
- HEPCKMNLFZYLRH-UHFFFAOYSA-N 4-[3-[2-(azetidin-1-yl)-3-[(3-chlorophenyl)methyl]-2,3-dihydro-1h-inden-5-yl]azetidin-1-yl]sulfonyl-1-methylpyrazole Chemical compound C1=NN(C)C=C1S(=O)(=O)N1CC(C=2C=C3C(CC=4C=C(Cl)C=CC=4)C(CC3=CC=2)N2CCC2)C1 HEPCKMNLFZYLRH-UHFFFAOYSA-N 0.000 claims 1
- HIJHWBKWTPJFCA-UHFFFAOYSA-N 4-[3-[2-(azetidin-1-yl)-3-[(3-chlorophenyl)methyl]-6-fluoro-2,3-dihydro-1h-inden-5-yl]azetidin-1-yl]sulfonyl-1-methylimidazole Chemical compound CN1C=NC(S(=O)(=O)N2CC(C2)C=2C(=CC=3CC(C(CC=4C=C(Cl)C=CC=4)C=3C=2)N2CCC2)F)=C1 HIJHWBKWTPJFCA-UHFFFAOYSA-N 0.000 claims 1
- BGHCBABZRTXRHI-UHFFFAOYSA-N 4-[3-[2-(azetidin-1-yl)-3-[(3-chlorophenyl)methyl]-6-fluoro-2,3-dihydro-1h-inden-5-yl]azetidin-1-yl]sulfonyl-1-methylpyrazole Chemical compound C1=NN(C)C=C1S(=O)(=O)N1CC(C=2C(=CC=3CC(C(CC=4C=C(Cl)C=CC=4)C=3C=2)N2CCC2)F)C1 BGHCBABZRTXRHI-UHFFFAOYSA-N 0.000 claims 1
- KPJSUKLUDRNVHD-UHFFFAOYSA-N 4-[3-[2-(azetidin-1-yl)-3-[(3-fluorophenyl)methyl]-2,3-dihydro-1h-inden-5-yl]azetidin-1-yl]sulfonyl-1-methylimidazole Chemical compound CN1C=NC(S(=O)(=O)N2CC(C2)C=2C=C3C(CC=4C=C(F)C=CC=4)C(CC3=CC=2)N2CCC2)=C1 KPJSUKLUDRNVHD-UHFFFAOYSA-N 0.000 claims 1
- QGVPXPFNVBXYKU-UHFFFAOYSA-N 4-[3-[2-(azetidin-1-yl)-3-[(3-fluorophenyl)methyl]-2,3-dihydro-1h-inden-5-yl]azetidin-1-yl]sulfonyl-1-methylpyrazole Chemical compound C1=NN(C)C=C1S(=O)(=O)N1CC(C=2C=C3C(CC=4C=C(F)C=CC=4)C(CC3=CC=2)N2CCC2)C1 QGVPXPFNVBXYKU-UHFFFAOYSA-N 0.000 claims 1
- DLIKIAQHVHVQSO-UHFFFAOYSA-N 4-[3-[2-(azetidin-1-yl)-3-[[3-(trifluoromethyl)phenyl]methyl]-2,3-dihydro-1h-inden-5-yl]azetidin-1-yl]sulfonyl-1-methylpyrazole Chemical compound C1=NN(C)C=C1S(=O)(=O)N1CC(C=2C=C3C(CC=4C=C(C=CC=4)C(F)(F)F)C(CC3=CC=2)N2CCC2)C1 DLIKIAQHVHVQSO-UHFFFAOYSA-N 0.000 claims 1
- VNGICMAWLJEXID-UHFFFAOYSA-N 4-[3-[2-(azetidin-1-yl)-3-benzyl-2,3-dihydro-1h-inden-5-yl]azetidin-1-yl]sulfonyl-1-methylimidazole Chemical compound CN1C=NC(S(=O)(=O)N2CC(C2)C=2C=C3C(CC=4C=CC=CC=4)C(CC3=CC=2)N2CCC2)=C1 VNGICMAWLJEXID-UHFFFAOYSA-N 0.000 claims 1
- YNTWFWGPTFONTH-UHFFFAOYSA-N 4-[3-[2-(azetidin-1-yl)-3-benzyl-2,3-dihydro-1h-inden-5-yl]azetidin-1-yl]sulfonyl-1-methylpyrazole Chemical compound C1=NN(C)C=C1S(=O)(=O)N1CC(C=2C=C3C(CC=4C=CC=CC=4)C(CC3=CC=2)N2CCC2)C1 YNTWFWGPTFONTH-UHFFFAOYSA-N 0.000 claims 1
- HXQAIPDXOAPJNU-UHFFFAOYSA-N 4-[3-[2-(azetidin-1-yl)-3-benzyl-6-fluoro-2,3-dihydro-1h-inden-5-yl]azetidin-1-yl]sulfonyl-1-methylimidazole Chemical compound CN1C=NC(S(=O)(=O)N2CC(C2)C=2C(=CC=3CC(C(CC=4C=CC=CC=4)C=3C=2)N2CCC2)F)=C1 HXQAIPDXOAPJNU-UHFFFAOYSA-N 0.000 claims 1
- MCOVMTUVMZBOAA-UHFFFAOYSA-N 4-[3-[2-(azetidin-1-yl)-3-benzyl-6-fluoro-2,3-dihydro-1h-inden-5-yl]azetidin-1-yl]sulfonyl-1-methylpyrazole Chemical compound C1=NN(C)C=C1S(=O)(=O)N1CC(C=2C(=CC=3CC(C(CC=4C=CC=CC=4)C=3C=2)N2CCC2)F)C1 MCOVMTUVMZBOAA-UHFFFAOYSA-N 0.000 claims 1
- KJOXQJYCGHSQIW-UHFFFAOYSA-N 4-[3-[2-(azetidin-1-yl)-6-fluoro-3-[(3-fluorophenyl)methyl]-2,3-dihydro-1h-inden-5-yl]azetidin-1-yl]sulfonyl-1-methylimidazole Chemical compound CN1C=NC(S(=O)(=O)N2CC(C2)C=2C(=CC=3CC(C(CC=4C=C(F)C=CC=4)C=3C=2)N2CCC2)F)=C1 KJOXQJYCGHSQIW-UHFFFAOYSA-N 0.000 claims 1
- CMYRWPCROOTRCL-UHFFFAOYSA-N 4-[3-[2-(azetidin-1-yl)-6-fluoro-3-[(3-fluorophenyl)methyl]-2,3-dihydro-1h-inden-5-yl]azetidin-1-yl]sulfonyl-1-methylpyrazole Chemical compound C1=NN(C)C=C1S(=O)(=O)N1CC(C=2C(=CC=3CC(C(CC=4C=C(F)C=CC=4)C=3C=2)N2CCC2)F)C1 CMYRWPCROOTRCL-UHFFFAOYSA-N 0.000 claims 1
- LNBZCGLYWRGCMB-UHFFFAOYSA-N 4-[3-[2-(azetidin-1-yl)-6-fluoro-3-[[3-(trifluoromethyl)phenyl]methyl]-2,3-dihydro-1h-inden-5-yl]azetidin-1-yl]sulfonyl-1-methylpyrazole Chemical compound C1=NN(C)C=C1S(=O)(=O)N1CC(C=2C(=CC=3CC(C(CC=4C=C(C=CC=4)C(F)(F)F)C=3C=2)N2CCC2)F)C1 LNBZCGLYWRGCMB-UHFFFAOYSA-N 0.000 claims 1
- RCZSGDFHTQLLHT-UHFFFAOYSA-N 5-fluoro-1-[(3-fluorophenyl)methyl]-n-methyl-6-[1-(1-methylimidazol-4-yl)sulfonylazetidin-3-yl]-2,3-dihydro-1h-inden-2-amine Chemical compound CNC1CC2=CC(F)=C(C3CN(C3)S(=O)(=O)C=3N=CN(C)C=3)C=C2C1CC1=CC=CC(F)=C1 RCZSGDFHTQLLHT-UHFFFAOYSA-N 0.000 claims 1
- ZLAYSLGRESUZJV-UHFFFAOYSA-N 5-fluoro-1-[(3-fluorophenyl)methyl]-n-methyl-6-[1-(1-methylpyrazol-4-yl)sulfonylazetidin-3-yl]-2,3-dihydro-1h-inden-2-amine Chemical compound CNC1CC2=CC(F)=C(C3CN(C3)S(=O)(=O)C3=CN(C)N=C3)C=C2C1CC1=CC=CC(F)=C1 ZLAYSLGRESUZJV-UHFFFAOYSA-N 0.000 claims 1
- RKHMSDGSIAJYBQ-UHFFFAOYSA-N 5-fluoro-n-methyl-6-[1-(1-methylimidazol-4-yl)sulfonylazetidin-3-yl]-1-[[3-(trifluoromethyl)phenyl]methyl]-2,3-dihydro-1h-inden-2-amine Chemical compound CNC1CC2=CC(F)=C(C3CN(C3)S(=O)(=O)C=3N=CN(C)C=3)C=C2C1CC1=CC=CC(C(F)(F)F)=C1 RKHMSDGSIAJYBQ-UHFFFAOYSA-N 0.000 claims 1
- ZHJGOPLLIKZTPK-UHFFFAOYSA-N 5-fluoro-n-methyl-6-[1-(1-methylpyrazol-4-yl)sulfonylazetidin-3-yl]-1-[[3-(trifluoromethyl)phenyl]methyl]-2,3-dihydro-1h-inden-2-amine Chemical compound CNC1CC2=CC(F)=C(C3CN(C3)S(=O)(=O)C3=CN(C)N=C3)C=C2C1CC1=CC=CC(C(F)(F)F)=C1 ZHJGOPLLIKZTPK-UHFFFAOYSA-N 0.000 claims 1
- REBWKADHELECBL-UHFFFAOYSA-N 6-(1-cyclobutylsulfonylazetidin-3-yl)-1-[(3-fluorophenyl)methyl]-n-methyl-2,3-dihydro-1h-inden-2-amine Chemical compound CNC1CC2=CC=C(C3CN(C3)S(=O)(=O)C3CCC3)C=C2C1CC1=CC=CC(F)=C1 REBWKADHELECBL-UHFFFAOYSA-N 0.000 claims 1
- BFMXGIGPYFUYCO-UHFFFAOYSA-N 6-(1-cyclobutylsulfonylazetidin-3-yl)-5-fluoro-1-[(3-fluorophenyl)methyl]-n-methyl-2,3-dihydro-1h-inden-2-amine Chemical compound CNC1CC2=CC(F)=C(C3CN(C3)S(=O)(=O)C3CCC3)C=C2C1CC1=CC=CC(F)=C1 BFMXGIGPYFUYCO-UHFFFAOYSA-N 0.000 claims 1
- RQHFSTRTVKNVAQ-UHFFFAOYSA-N 6-(1-cyclobutylsulfonylazetidin-3-yl)-5-fluoro-n-methyl-1-[[3-(trifluoromethyl)phenyl]methyl]-2,3-dihydro-1h-inden-2-amine Chemical class CNC1CC2=CC(F)=C(C3CN(C3)S(=O)(=O)C3CCC3)C=C2C1CC1=CC=CC(C(F)(F)F)=C1 RQHFSTRTVKNVAQ-UHFFFAOYSA-N 0.000 claims 1
- AJMWVVQEWXEWOQ-UHFFFAOYSA-N 6-(1-cyclobutylsulfonylazetidin-3-yl)-n-methyl-1-[[3-(trifluoromethyl)phenyl]methyl]-2,3-dihydro-1h-inden-2-amine Chemical compound CNC1CC2=CC=C(C3CN(C3)S(=O)(=O)C3CCC3)C=C2C1CC1=CC=CC(C(F)(F)F)=C1 AJMWVVQEWXEWOQ-UHFFFAOYSA-N 0.000 claims 1
- QBHXKROUVNTTJN-UHFFFAOYSA-N 6-[1-(cyclopropylmethylsulfonyl)azetidin-3-yl]-1-[(3-fluorophenyl)methyl]-n-methyl-2,3-dihydro-1h-inden-2-amine Chemical compound CNC1CC2=CC=C(C3CN(C3)S(=O)(=O)CC3CC3)C=C2C1CC1=CC=CC(F)=C1 QBHXKROUVNTTJN-UHFFFAOYSA-N 0.000 claims 1
- KXBIURLLBYGJMG-UHFFFAOYSA-N 6-[1-(cyclopropylmethylsulfonyl)azetidin-3-yl]-5-fluoro-1-[(3-fluorophenyl)methyl]-n-methyl-2,3-dihydro-1h-inden-2-amine Chemical compound CNC1CC2=CC(F)=C(C3CN(C3)S(=O)(=O)CC3CC3)C=C2C1CC1=CC=CC(F)=C1 KXBIURLLBYGJMG-UHFFFAOYSA-N 0.000 claims 1
- YJNVNPHVIIUMDX-UHFFFAOYSA-N 6-[1-(cyclopropylmethylsulfonyl)azetidin-3-yl]-n-methyl-1-[[3-(trifluoromethyl)phenyl]methyl]-2,3-dihydro-1h-inden-2-amine Chemical compound CNC1CC2=CC=C(C3CN(C3)S(=O)(=O)CC3CC3)C=C2C1CC1=CC=CC(C(F)(F)F)=C1 YJNVNPHVIIUMDX-UHFFFAOYSA-N 0.000 claims 1
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- 208000002193 Pain Diseases 0.000 claims 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- OBXZYYDSYUNGFQ-UHFFFAOYSA-N ethyl n-[1-benzyl-5-fluoro-6-[[(1-methylimidazol-4-yl)sulfonylamino]methyl]-2,3-dihydro-1h-inden-2-yl]carbamate Chemical compound C1=C2C(CC=3C=CC=CC=3)C(NC(=O)OCC)CC2=CC(F)=C1CNS(=O)(=O)C1=CN(C)C=N1 OBXZYYDSYUNGFQ-UHFFFAOYSA-N 0.000 claims 1
- YNJQBLJISXTPMZ-UHFFFAOYSA-N ethyl n-[1-benzyl-6-[2-[(1-methylimidazol-2-yl)sulfonylamino]ethoxy]-2,3-dihydro-1h-inden-2-yl]carbamate Chemical compound C1=C2C(CC=3C=CC=CC=3)C(NC(=O)OCC)CC2=CC=C1OCCNS(=O)(=O)C1=NC=CN1C YNJQBLJISXTPMZ-UHFFFAOYSA-N 0.000 claims 1
- QKFWCNISSZNCLY-UHFFFAOYSA-N ethyl n-[1-benzyl-6-[2-[(1-methylimidazol-4-yl)sulfonylamino]ethoxy]-2,3-dihydro-1h-inden-2-yl]carbamate Chemical compound C1=C2C(CC=3C=CC=CC=3)C(NC(=O)OCC)CC2=CC=C1OCCNS(=O)(=O)C1=CN(C)C=N1 QKFWCNISSZNCLY-UHFFFAOYSA-N 0.000 claims 1
- 125000005549 heteroarylene group Chemical group 0.000 claims 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
- JFBMXDLNOOUNPJ-UHFFFAOYSA-N n-[2-[[2-(azetidin-1-yl)-3-[(3-chlorophenyl)methyl]-2,3-dihydro-1h-inden-5-yl]oxy]ethyl]-1-cyclopropylmethanesulfonamide Chemical compound ClC1=CC=CC(CC2C3=CC(OCCNS(=O)(=O)CC4CC4)=CC=C3CC2N2CCC2)=C1 JFBMXDLNOOUNPJ-UHFFFAOYSA-N 0.000 claims 1
- XMURHHWQIFNOAM-UHFFFAOYSA-N n-[2-[[2-(azetidin-1-yl)-3-[(3-chlorophenyl)methyl]-2,3-dihydro-1h-inden-5-yl]oxy]ethyl]-1-methylimidazole-4-sulfonamide Chemical compound CN1C=NC(S(=O)(=O)NCCOC=2C=C3C(CC=4C=C(Cl)C=CC=4)C(CC3=CC=2)N2CCC2)=C1 XMURHHWQIFNOAM-UHFFFAOYSA-N 0.000 claims 1
- HBKFNLVJGAMMKX-UHFFFAOYSA-N n-[2-[[2-(azetidin-1-yl)-3-[(3-chlorophenyl)methyl]-2,3-dihydro-1h-inden-5-yl]oxy]ethyl]-1-methylpyrazole-4-sulfonamide Chemical compound C1=NN(C)C=C1S(=O)(=O)NCCOC1=CC=C(CC(C2CC=3C=C(Cl)C=CC=3)N3CCC3)C2=C1 HBKFNLVJGAMMKX-UHFFFAOYSA-N 0.000 claims 1
- DLNJSNCDWAMHHW-UHFFFAOYSA-N n-[2-[[2-(azetidin-1-yl)-3-[(3-chlorophenyl)methyl]-2,3-dihydro-1h-inden-5-yl]oxy]ethyl]cyclobutanesulfonamide Chemical compound ClC1=CC=CC(CC2C3=CC(OCCNS(=O)(=O)C4CCC4)=CC=C3CC2N2CCC2)=C1 DLNJSNCDWAMHHW-UHFFFAOYSA-N 0.000 claims 1
- YYZBYPQCMHRZOG-UHFFFAOYSA-N n-[2-[[2-(azetidin-1-yl)-3-[(3-chlorophenyl)methyl]-6-fluoro-2,3-dihydro-1h-inden-5-yl]oxy]ethyl]-1-cyclopropylmethanesulfonamide Chemical compound C1=2C=C(OCCNS(=O)(=O)CC3CC3)C(F)=CC=2CC(N2CCC2)C1CC1=CC=CC(Cl)=C1 YYZBYPQCMHRZOG-UHFFFAOYSA-N 0.000 claims 1
- RZUQFCWSMYPUMS-UHFFFAOYSA-N n-[2-[[2-(azetidin-1-yl)-3-[(3-chlorophenyl)methyl]-6-fluoro-2,3-dihydro-1h-inden-5-yl]oxy]ethyl]-1-methylimidazole-4-sulfonamide Chemical compound CN1C=NC(S(=O)(=O)NCCOC=2C(=CC=3CC(C(CC=4C=C(Cl)C=CC=4)C=3C=2)N2CCC2)F)=C1 RZUQFCWSMYPUMS-UHFFFAOYSA-N 0.000 claims 1
- AYISXXIWIJLTSG-UHFFFAOYSA-N n-[2-[[2-(azetidin-1-yl)-3-[(3-chlorophenyl)methyl]-6-fluoro-2,3-dihydro-1h-inden-5-yl]oxy]ethyl]-1-methylpyrazole-4-sulfonamide Chemical compound C1=NN(C)C=C1S(=O)(=O)NCCOC(C(=C1)F)=CC2=C1CC(N1CCC1)C2CC1=CC=CC(Cl)=C1 AYISXXIWIJLTSG-UHFFFAOYSA-N 0.000 claims 1
- BZPZVVYPYOTQDH-UHFFFAOYSA-N n-[2-[[2-(azetidin-1-yl)-3-[(3-fluorophenyl)methyl]-2,3-dihydro-1h-inden-5-yl]oxy]ethyl]-1-cyclopropylmethanesulfonamide Chemical compound FC1=CC=CC(CC2C3=CC(OCCNS(=O)(=O)CC4CC4)=CC=C3CC2N2CCC2)=C1 BZPZVVYPYOTQDH-UHFFFAOYSA-N 0.000 claims 1
- AHRUPWPAHJUKAB-UHFFFAOYSA-N n-[2-[[2-(azetidin-1-yl)-3-[(3-fluorophenyl)methyl]-2,3-dihydro-1h-inden-5-yl]oxy]ethyl]-1-methylimidazole-4-sulfonamide Chemical compound CN1C=NC(S(=O)(=O)NCCOC=2C=C3C(CC=4C=C(F)C=CC=4)C(CC3=CC=2)N2CCC2)=C1 AHRUPWPAHJUKAB-UHFFFAOYSA-N 0.000 claims 1
- OXWNTKDABPVWQH-UHFFFAOYSA-N n-[2-[[2-(azetidin-1-yl)-3-[(3-fluorophenyl)methyl]-2,3-dihydro-1h-inden-5-yl]oxy]ethyl]-1-methylpyrazole-4-sulfonamide Chemical compound C1=NN(C)C=C1S(=O)(=O)NCCOC1=CC=C(CC(C2CC=3C=C(F)C=CC=3)N3CCC3)C2=C1 OXWNTKDABPVWQH-UHFFFAOYSA-N 0.000 claims 1
- MHBZPACDIACANC-UHFFFAOYSA-N n-[2-[[2-(azetidin-1-yl)-3-[(3-fluorophenyl)methyl]-2,3-dihydro-1h-inden-5-yl]oxy]ethyl]cyclobutanesulfonamide Chemical compound FC1=CC=CC(CC2C3=CC(OCCNS(=O)(=O)C4CCC4)=CC=C3CC2N2CCC2)=C1 MHBZPACDIACANC-UHFFFAOYSA-N 0.000 claims 1
- VSYJTZDEDDGDTF-UHFFFAOYSA-N n-[2-[[2-(azetidin-1-yl)-3-benzyl-2,3-dihydro-1h-inden-5-yl]oxy]ethyl]-1-cyclopropylmethanesulfonamide Chemical compound C=1C=C2CC(N3CCC3)C(CC=3C=CC=CC=3)C2=CC=1OCCNS(=O)(=O)CC1CC1 VSYJTZDEDDGDTF-UHFFFAOYSA-N 0.000 claims 1
- KPCBGDMWFRJVEW-UHFFFAOYSA-N n-[2-[[2-(azetidin-1-yl)-3-benzyl-2,3-dihydro-1h-inden-5-yl]oxy]ethyl]-1-methylpyrazole-4-sulfonamide Chemical compound C1=NN(C)C=C1S(=O)(=O)NCCOC1=CC=C(CC(C2CC=3C=CC=CC=3)N3CCC3)C2=C1 KPCBGDMWFRJVEW-UHFFFAOYSA-N 0.000 claims 1
- DAYVXDDBZUWWNR-UHFFFAOYSA-N n-[2-[[2-(azetidin-1-yl)-3-benzyl-2,3-dihydro-1h-inden-5-yl]oxy]ethyl]cyclobutanesulfonamide Chemical compound C1CCC1S(=O)(=O)NCCOC(C=C12)=CC=C1CC(N1CCC1)C2CC1=CC=CC=C1 DAYVXDDBZUWWNR-UHFFFAOYSA-N 0.000 claims 1
- OBOUDLIOARIIAI-UHFFFAOYSA-N n-[2-[[2-(azetidin-1-yl)-3-benzyl-6-fluoro-2,3-dihydro-1h-inden-5-yl]oxy]ethyl]-1-methylimidazole-4-sulfonamide Chemical compound CN1C=NC(S(=O)(=O)NCCOC=2C(=CC=3CC(C(CC=4C=CC=CC=4)C=3C=2)N2CCC2)F)=C1 OBOUDLIOARIIAI-UHFFFAOYSA-N 0.000 claims 1
- BFIAZCWUDUTZEX-UHFFFAOYSA-N n-[2-[[2-(azetidin-1-yl)-3-benzyl-6-fluoro-2,3-dihydro-1h-inden-5-yl]oxy]ethyl]-1-methylpyrazole-4-sulfonamide Chemical compound C1=NN(C)C=C1S(=O)(=O)NCCOC(C(=C1)F)=CC2=C1CC(N1CCC1)C2CC1=CC=CC=C1 BFIAZCWUDUTZEX-UHFFFAOYSA-N 0.000 claims 1
- NFRCIFUVPOOYAW-UHFFFAOYSA-N n-[2-[[2-(azetidin-1-yl)-3-benzyl-6-fluoro-2,3-dihydro-1h-inden-5-yl]oxy]ethyl]cyclobutanesulfonamide Chemical compound C1=2C=C(OCCNS(=O)(=O)C3CCC3)C(F)=CC=2CC(N2CCC2)C1CC1=CC=CC=C1 NFRCIFUVPOOYAW-UHFFFAOYSA-N 0.000 claims 1
- GYNVIKWNIXDMDE-UHFFFAOYSA-N n-[2-[[2-(azetidin-1-yl)-6-fluoro-3-[(3-fluorophenyl)methyl]-2,3-dihydro-1h-inden-5-yl]oxy]ethyl]-1-cyclopropylmethanesulfonamide Chemical compound FC1=CC=CC(CC2C3=CC(OCCNS(=O)(=O)CC4CC4)=C(F)C=C3CC2N2CCC2)=C1 GYNVIKWNIXDMDE-UHFFFAOYSA-N 0.000 claims 1
- ZINGGXIRMPREGH-UHFFFAOYSA-N n-[2-[[2-(azetidin-1-yl)-6-fluoro-3-[(3-fluorophenyl)methyl]-2,3-dihydro-1h-inden-5-yl]oxy]ethyl]-1-methylimidazole-4-sulfonamide Chemical compound CN1C=NC(S(=O)(=O)NCCOC=2C(=CC=3CC(C(CC=4C=C(F)C=CC=4)C=3C=2)N2CCC2)F)=C1 ZINGGXIRMPREGH-UHFFFAOYSA-N 0.000 claims 1
- CASYYPCDSHCPKO-UHFFFAOYSA-N n-[2-[[2-(azetidin-1-yl)-6-fluoro-3-[(3-fluorophenyl)methyl]-2,3-dihydro-1h-inden-5-yl]oxy]ethyl]-1-methylpyrazole-4-sulfonamide Chemical compound C1=NN(C)C=C1S(=O)(=O)NCCOC(C(=C1)F)=CC2=C1CC(N1CCC1)C2CC1=CC=CC(F)=C1 CASYYPCDSHCPKO-UHFFFAOYSA-N 0.000 claims 1
- OQPCPPDVPKMSFE-UHFFFAOYSA-N n-[2-[[2-(azetidin-1-yl)-6-fluoro-3-[[3-(trifluoromethyl)phenyl]methyl]-2,3-dihydro-1h-inden-5-yl]oxy]ethyl]-1-methylimidazole-4-sulfonamide Chemical compound CN1C=NC(S(=O)(=O)NCCOC=2C(=CC=3CC(C(CC=4C=C(C=CC=4)C(F)(F)F)C=3C=2)N2CCC2)F)=C1 OQPCPPDVPKMSFE-UHFFFAOYSA-N 0.000 claims 1
- UODMVPOXOSKDDB-UHFFFAOYSA-N n-[2-[[2-(azetidin-1-yl)-6-fluoro-3-[[3-(trifluoromethyl)phenyl]methyl]-2,3-dihydro-1h-inden-5-yl]oxy]ethyl]-1-methylpyrazole-4-sulfonamide Chemical compound C1=NN(C)C=C1S(=O)(=O)NCCOC(C(=C1)F)=CC2=C1CC(N1CCC1)C2CC1=CC=CC(C(F)(F)F)=C1 UODMVPOXOSKDDB-UHFFFAOYSA-N 0.000 claims 1
- CDYJNLKDXICBJN-UHFFFAOYSA-N n-[2-[[2-(azetidin-1-yl)-6-fluoro-3-[[3-(trifluoromethyl)phenyl]methyl]-2,3-dihydro-1h-inden-5-yl]oxy]ethyl]cyclobutanesulfonamide Chemical compound C1=2C=C(OCCNS(=O)(=O)C3CCC3)C(F)=CC=2CC(N2CCC2)C1CC1=CC=CC(C(F)(F)F)=C1 CDYJNLKDXICBJN-UHFFFAOYSA-N 0.000 claims 1
- LLLZZQBMXXTXCM-UHFFFAOYSA-N n-[2-[[2-(methylamino)-3-[[3-(trifluoromethyl)phenyl]methyl]-2,3-dihydro-1h-inden-5-yl]oxy]ethyl]cyclobutanesulfonamide Chemical compound C1=C2C(CC=3C=C(C=CC=3)C(F)(F)F)C(NC)CC2=CC=C1OCCNS(=O)(=O)C1CCC1 LLLZZQBMXXTXCM-UHFFFAOYSA-N 0.000 claims 1
- RGDZEIKISCIYMZ-UHFFFAOYSA-N n-[2-[[3-[(3-chlorophenyl)methyl]-2-(methylamino)-2,3-dihydro-1h-inden-5-yl]oxy]ethyl]-1-cyclopropylmethanesulfonamide Chemical compound C1=C2C(CC=3C=C(Cl)C=CC=3)C(NC)CC2=CC=C1OCCNS(=O)(=O)CC1CC1 RGDZEIKISCIYMZ-UHFFFAOYSA-N 0.000 claims 1
- YOZWPVZQFIPDOT-UHFFFAOYSA-N n-[2-[[3-[(3-chlorophenyl)methyl]-2-(methylamino)-2,3-dihydro-1h-inden-5-yl]oxy]ethyl]-1-methylimidazole-4-sulfonamide Chemical compound C1=C2C(CC=3C=C(Cl)C=CC=3)C(NC)CC2=CC=C1OCCNS(=O)(=O)C1=CN(C)C=N1 YOZWPVZQFIPDOT-UHFFFAOYSA-N 0.000 claims 1
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- IMJACZVSDLTEQO-UHFFFAOYSA-N n-[2-[[3-[(3-chlorophenyl)methyl]-6-fluoro-2-(methylamino)-2,3-dihydro-1h-inden-5-yl]oxy]ethyl]-1-methylpyrazole-4-sulfonamide Chemical compound C1=C2C(CC=3C=C(Cl)C=CC=3)C(NC)CC2=CC(F)=C1OCCNS(=O)(=O)C=1C=NN(C)C=1 IMJACZVSDLTEQO-UHFFFAOYSA-N 0.000 claims 1
- BXHUENYHSJLHBA-UHFFFAOYSA-N n-[2-[[3-[(3-chlorophenyl)methyl]-6-fluoro-2-(methylamino)-2,3-dihydro-1h-inden-5-yl]oxy]ethyl]cyclobutanesulfonamide Chemical compound C1=C2C(CC=3C=C(Cl)C=CC=3)C(NC)CC2=CC(F)=C1OCCNS(=O)(=O)C1CCC1 BXHUENYHSJLHBA-UHFFFAOYSA-N 0.000 claims 1
- UWQRBHZCRSRQRJ-UHFFFAOYSA-N n-[2-[[3-[(3-fluorophenyl)methyl]-2-(methylamino)-2,3-dihydro-1h-inden-5-yl]oxy]ethyl]-1-methylimidazole-4-sulfonamide Chemical compound C1=C2C(CC=3C=C(F)C=CC=3)C(NC)CC2=CC=C1OCCNS(=O)(=O)C1=CN(C)C=N1 UWQRBHZCRSRQRJ-UHFFFAOYSA-N 0.000 claims 1
- MRFDQQIIJXDYJI-UHFFFAOYSA-N n-[2-[[3-[(3-fluorophenyl)methyl]-2-(methylamino)-2,3-dihydro-1h-inden-5-yl]oxy]ethyl]-1-methylpyrazole-4-sulfonamide Chemical compound C1=C2C(CC=3C=C(F)C=CC=3)C(NC)CC2=CC=C1OCCNS(=O)(=O)C=1C=NN(C)C=1 MRFDQQIIJXDYJI-UHFFFAOYSA-N 0.000 claims 1
- OXBMHUZNWDFWKB-UHFFFAOYSA-N n-[2-[[3-[(3-fluorophenyl)methyl]-2-(methylamino)-2,3-dihydro-1h-inden-5-yl]oxy]ethyl]cyclobutanesulfonamide Chemical compound C1=C2C(CC=3C=C(F)C=CC=3)C(NC)CC2=CC=C1OCCNS(=O)(=O)C1CCC1 OXBMHUZNWDFWKB-UHFFFAOYSA-N 0.000 claims 1
- BGDPWRNLGPWWNO-UHFFFAOYSA-N n-[2-[[3-benzyl-2-(3,3-dimethylazetidin-1-yl)-2,3-dihydro-1h-inden-5-yl]oxy]ethyl]-1-methylimidazole-4-sulfonamide Chemical compound CN1C=NC(S(=O)(=O)NCCOC=2C=C3C(CC=4C=CC=CC=4)C(CC3=CC=2)N2CC(C)(C)C2)=C1 BGDPWRNLGPWWNO-UHFFFAOYSA-N 0.000 claims 1
- OMUNIDNULDRORK-UHFFFAOYSA-N n-[2-[[3-benzyl-2-(3-methylazetidin-1-yl)-2,3-dihydro-1h-inden-5-yl]oxy]ethyl]-1-methylimidazole-4-sulfonamide Chemical compound C1C(C)CN1C1C(CC=2C=CC=CC=2)C2=CC(OCCNS(=O)(=O)C=3N=CN(C)C=3)=CC=C2C1 OMUNIDNULDRORK-UHFFFAOYSA-N 0.000 claims 1
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- LJMALDIUXDPRGY-UHFFFAOYSA-N n-[2-[[3-benzyl-2-(methylamino)-2,3-dihydro-1h-inden-5-yl]oxy]ethyl]-1-methylpyrazole-4-sulfonamide Chemical compound C1=C2C(CC=3C=CC=CC=3)C(NC)CC2=CC=C1OCCNS(=O)(=O)C=1C=NN(C)C=1 LJMALDIUXDPRGY-UHFFFAOYSA-N 0.000 claims 1
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- QIGLPZPDVRPZSW-UHFFFAOYSA-N n-[2-[[6-fluoro-2-(methylamino)-3-[[3-(trifluoromethyl)phenyl]methyl]-2,3-dihydro-1h-inden-5-yl]oxy]ethyl]-1-methylpyrazole-4-sulfonamide Chemical compound C1=C2C(CC=3C=C(C=CC=3)C(F)(F)F)C(NC)CC2=CC(F)=C1OCCNS(=O)(=O)C=1C=NN(C)C=1 QIGLPZPDVRPZSW-UHFFFAOYSA-N 0.000 claims 1
- GSGGGGYYEAOOGZ-UHFFFAOYSA-N n-[2-[[6-fluoro-2-(methylamino)-3-[[3-(trifluoromethyl)phenyl]methyl]-2,3-dihydro-1h-inden-5-yl]oxy]ethyl]cyclobutanesulfonamide Chemical compound C1=C2C(CC=3C=C(C=CC=3)C(F)(F)F)C(NC)CC2=CC(F)=C1OCCNS(=O)(=O)C1CCC1 GSGGGGYYEAOOGZ-UHFFFAOYSA-N 0.000 claims 1
- KVOZMVRQKFOSOK-UHFFFAOYSA-N n-[2-[[6-fluoro-3-[(3-fluorophenyl)methyl]-2-(methylamino)-2,3-dihydro-1h-inden-5-yl]oxy]ethyl]-1-methylimidazole-4-sulfonamide Chemical compound C1=C2C(CC=3C=C(F)C=CC=3)C(NC)CC2=CC(F)=C1OCCNS(=O)(=O)C1=CN(C)C=N1 KVOZMVRQKFOSOK-UHFFFAOYSA-N 0.000 claims 1
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- JECCAYNKSCZQNF-TZIWHRDSSA-N n-[[(2r,3r)-3-benzyl-6-fluoro-2-(methylamino)-2,3-dihydro-1h-inden-5-yl]methyl]-1-methylimidazole-4-sulfonamide Chemical compound C([C@H]([C@@H](C1=C2)CC=3C=CC=CC=3)NC)C1=CC(F)=C2CNS(=O)(=O)C1=CN(C)C=N1 JECCAYNKSCZQNF-TZIWHRDSSA-N 0.000 claims 1
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- QSNVSJWHBNJVHJ-UHFFFAOYSA-N n-[[2-(azetidin-1-yl)-3-[(3-chlorophenyl)methyl]-2,3-dihydro-1h-inden-5-yl]methyl]-1-methylimidazole-4-sulfonamide Chemical compound CN1C=NC(S(=O)(=O)NCC=2C=C3C(CC=4C=C(Cl)C=CC=4)C(CC3=CC=2)N2CCC2)=C1 QSNVSJWHBNJVHJ-UHFFFAOYSA-N 0.000 claims 1
- LKGBXLGGXYGAPU-UHFFFAOYSA-N n-[[2-(azetidin-1-yl)-3-[(3-chlorophenyl)methyl]-2,3-dihydro-1h-inden-5-yl]methyl]-1-methylpyrazole-4-sulfonamide Chemical compound C1=NN(C)C=C1S(=O)(=O)NCC1=CC=C(CC(C2CC=3C=C(Cl)C=CC=3)N3CCC3)C2=C1 LKGBXLGGXYGAPU-UHFFFAOYSA-N 0.000 claims 1
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- OQDYXXCPQULSTI-UHFFFAOYSA-N n-[[2-(azetidin-1-yl)-3-[(3-chlorophenyl)methyl]-6-fluoro-2,3-dihydro-1h-inden-5-yl]methyl]-1-methylpyrazole-4-sulfonamide Chemical compound C1=NN(C)C=C1S(=O)(=O)NCC(C(=C1)F)=CC2=C1CC(N1CCC1)C2CC1=CC=CC(Cl)=C1 OQDYXXCPQULSTI-UHFFFAOYSA-N 0.000 claims 1
- MEOZQEGXYIPTMO-UHFFFAOYSA-N n-[[2-(azetidin-1-yl)-3-[(3-chlorophenyl)methyl]-6-fluoro-2,3-dihydro-1h-inden-5-yl]methyl]cyclobutanesulfonamide Chemical compound C1=2C=C(CNS(=O)(=O)C3CCC3)C(F)=CC=2CC(N2CCC2)C1CC1=CC=CC(Cl)=C1 MEOZQEGXYIPTMO-UHFFFAOYSA-N 0.000 claims 1
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- UXPQKHREMPCXGX-UHFFFAOYSA-N n-[[2-(azetidin-1-yl)-3-[(3-fluorophenyl)methyl]-2,3-dihydro-1h-inden-5-yl]methyl]-1-methylpyrazole-4-sulfonamide Chemical compound C1=NN(C)C=C1S(=O)(=O)NCC1=CC=C(CC(C2CC=3C=C(F)C=CC=3)N3CCC3)C2=C1 UXPQKHREMPCXGX-UHFFFAOYSA-N 0.000 claims 1
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- OFBLYQFHNDOAAO-UHFFFAOYSA-N n-[[2-(azetidin-1-yl)-3-benzyl-2,3-dihydro-1h-inden-5-yl]methyl]-1-cyclopropylmethanesulfonamide Chemical compound C=1C=C2CC(N3CCC3)C(CC=3C=CC=CC=3)C2=CC=1CNS(=O)(=O)CC1CC1 OFBLYQFHNDOAAO-UHFFFAOYSA-N 0.000 claims 1
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- CYNMANAGXWHAHH-UHFFFAOYSA-N n-[[2-(azetidin-1-yl)-3-benzyl-6-fluoro-2,3-dihydro-1h-inden-5-yl]methyl]-1-cyclopropylmethanesulfonamide Chemical compound C1=2C=C(CNS(=O)(=O)CC3CC3)C(F)=CC=2CC(N2CCC2)C1CC1=CC=CC=C1 CYNMANAGXWHAHH-UHFFFAOYSA-N 0.000 claims 1
- KFUWFJIXYGKNDC-UHFFFAOYSA-N n-[[2-(azetidin-1-yl)-3-benzyl-6-fluoro-2,3-dihydro-1h-inden-5-yl]methyl]cyclobutanesulfonamide Chemical compound C1=2C=C(CNS(=O)(=O)C3CCC3)C(F)=CC=2CC(N2CCC2)C1CC1=CC=CC=C1 KFUWFJIXYGKNDC-UHFFFAOYSA-N 0.000 claims 1
- CIMHQCZETKZZCD-UHFFFAOYSA-N n-[[2-(azetidin-1-yl)-6-fluoro-3-[(3-fluorophenyl)methyl]-2,3-dihydro-1h-inden-5-yl]methyl]-1-methylimidazole-4-sulfonamide Chemical compound CN1C=NC(S(=O)(=O)NCC=2C(=CC=3CC(C(CC=4C=C(F)C=CC=4)C=3C=2)N2CCC2)F)=C1 CIMHQCZETKZZCD-UHFFFAOYSA-N 0.000 claims 1
- JJKPHBZTSWAQNF-UHFFFAOYSA-N n-[[2-(azetidin-1-yl)-6-fluoro-3-[(3-fluorophenyl)methyl]-2,3-dihydro-1h-inden-5-yl]methyl]-1-methylpyrazole-4-sulfonamide Chemical compound C1=NN(C)C=C1S(=O)(=O)NCC(C(=C1)F)=CC2=C1CC(N1CCC1)C2CC1=CC=CC(F)=C1 JJKPHBZTSWAQNF-UHFFFAOYSA-N 0.000 claims 1
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- GZUXNPWAQTZGHT-UHFFFAOYSA-N n-[[2-(azetidin-1-yl)-6-fluoro-3-[[3-(trifluoromethyl)phenyl]methyl]-2,3-dihydro-1h-inden-5-yl]methyl]-1-cyclopropylmethanesulfonamide Chemical compound C1=2C=C(CNS(=O)(=O)CC3CC3)C(F)=CC=2CC(N2CCC2)C1CC1=CC=CC(C(F)(F)F)=C1 GZUXNPWAQTZGHT-UHFFFAOYSA-N 0.000 claims 1
- GDCXFGIPAHDKEA-UHFFFAOYSA-N n-[[2-(azetidin-1-yl)-6-fluoro-3-[[3-(trifluoromethyl)phenyl]methyl]-2,3-dihydro-1h-inden-5-yl]methyl]-1-methylpyrazole-4-sulfonamide Chemical compound C1=NN(C)C=C1S(=O)(=O)NCC(C(=C1)F)=CC2=C1CC(N1CCC1)C2CC1=CC=CC(C(F)(F)F)=C1 GDCXFGIPAHDKEA-UHFFFAOYSA-N 0.000 claims 1
- RGYKMMFWZHPVSS-UHFFFAOYSA-N n-[[2-(azetidin-1-yl)-6-fluoro-3-[[3-(trifluoromethyl)phenyl]methyl]-2,3-dihydro-1h-inden-5-yl]methyl]cyclobutanesulfonamide Chemical compound C1=2C=C(CNS(=O)(=O)C3CCC3)C(F)=CC=2CC(N2CCC2)C1CC1=CC=CC(C(F)(F)F)=C1 RGYKMMFWZHPVSS-UHFFFAOYSA-N 0.000 claims 1
- BXSWVLSNCHLBSW-UHFFFAOYSA-N n-[[2-(methylamino)-3-[[3-(trifluoromethyl)phenyl]methyl]-2,3-dihydro-1h-inden-5-yl]methyl]cyclobutanesulfonamide Chemical compound C1=C2C(CC=3C=C(C=CC=3)C(F)(F)F)C(NC)CC2=CC=C1CNS(=O)(=O)C1CCC1 BXSWVLSNCHLBSW-UHFFFAOYSA-N 0.000 claims 1
- DZYIEXJADMWRRC-UHFFFAOYSA-N n-[[3-[(3-chlorophenyl)methyl]-2-(methylamino)-2,3-dihydro-1h-inden-5-yl]methyl]-1-cyclopropylmethanesulfonamide Chemical compound C1=C2C(CC=3C=C(Cl)C=CC=3)C(NC)CC2=CC=C1CNS(=O)(=O)CC1CC1 DZYIEXJADMWRRC-UHFFFAOYSA-N 0.000 claims 1
- JAHOPBLLTCIJMX-UHFFFAOYSA-N n-[[3-[(3-chlorophenyl)methyl]-2-(methylamino)-2,3-dihydro-1h-inden-5-yl]methyl]-1-methylimidazole-4-sulfonamide Chemical compound C1=C2C(CC=3C=C(Cl)C=CC=3)C(NC)CC2=CC=C1CNS(=O)(=O)C1=CN(C)C=N1 JAHOPBLLTCIJMX-UHFFFAOYSA-N 0.000 claims 1
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- NPGKTEOWJCYHGD-UHFFFAOYSA-N n-[[3-[(3-chlorophenyl)methyl]-6-fluoro-2-(methylamino)-2,3-dihydro-1h-inden-5-yl]methyl]-1-cyclopropylmethanesulfonamide Chemical compound C1=C2C(CC=3C=C(Cl)C=CC=3)C(NC)CC2=CC(F)=C1CNS(=O)(=O)CC1CC1 NPGKTEOWJCYHGD-UHFFFAOYSA-N 0.000 claims 1
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- QNDZLVKIZSWCHO-UHFFFAOYSA-N n-[[3-[(3-fluorophenyl)methyl]-2-(methylamino)-2,3-dihydro-1h-inden-5-yl]methyl]-1-methylpyrazole-4-sulfonamide Chemical compound C1=C2C(CC=3C=C(F)C=CC=3)C(NC)CC2=CC=C1CNS(=O)(=O)C=1C=NN(C)C=1 QNDZLVKIZSWCHO-UHFFFAOYSA-N 0.000 claims 1
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- KYIMDKYCUDTPDK-UHFFFAOYSA-N n-[[3-benzyl-2-(methylamino)-2,3-dihydro-1h-inden-5-yl]methyl]-1-methylpyrazole-4-sulfonamide Chemical compound C1=C2C(CC=3C=CC=CC=3)C(NC)CC2=CC=C1CNS(=O)(=O)C=1C=NN(C)C=1 KYIMDKYCUDTPDK-UHFFFAOYSA-N 0.000 claims 1
- QVVDHGASULONIT-UHFFFAOYSA-N n-[[3-benzyl-2-(methylamino)-2,3-dihydro-1h-inden-5-yl]methyl]cyclobutanesulfonamide Chemical compound C1=C2C(CC=3C=CC=CC=3)C(NC)CC2=CC=C1CNS(=O)(=O)C1CCC1 QVVDHGASULONIT-UHFFFAOYSA-N 0.000 claims 1
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- QYLAEZRRMPGRTC-UHFFFAOYSA-N n-[[6-fluoro-2-(methylamino)-3-[[3-(trifluoromethyl)phenyl]methyl]-2,3-dihydro-1h-inden-5-yl]methyl]-1-methylpyrazole-4-sulfonamide Chemical compound C1=C2C(CC=3C=C(C=CC=3)C(F)(F)F)C(NC)CC2=CC(F)=C1CNS(=O)(=O)C=1C=NN(C)C=1 QYLAEZRRMPGRTC-UHFFFAOYSA-N 0.000 claims 1
- GXSNQFROKMFQNA-UHFFFAOYSA-N n-[[6-fluoro-3-[(3-fluorophenyl)methyl]-2-(methylamino)-2,3-dihydro-1h-inden-5-yl]methyl]-1-methylimidazole-4-sulfonamide Chemical compound C1=C2C(CC=3C=C(F)C=CC=3)C(NC)CC2=CC(F)=C1CNS(=O)(=O)C1=CN(C)C=N1 GXSNQFROKMFQNA-UHFFFAOYSA-N 0.000 claims 1
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| CN103889968A (zh) | 2011-08-05 | 2014-06-25 | 艾伯维德国有限责任两合公司 | 氨基苯并二氢吡喃、氨基苯并二氢噻喃及氨基-1,2,3,4-四氢喹啉衍生物，包含这些化合物的药用组合物，及其在治疗中的用途 |
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| JP2016537323A (ja) | 2013-10-17 | 2016-12-01 | アッヴィ・ドイチュラント・ゲー・エム・ベー・ハー・ウント・コー・カー・ゲー | アミノクロマン誘導体、アミノチオクロマン誘導体およびアミノ−１，２，３，４−テトラヒドロキノリン誘導体、これらを含有する医薬組成物、および治療におけるこれらの使用 |
-
2011
- 2011-08-10 US US13/207,030 patent/US8846743B2/en active Active
- 2011-08-11 TW TW100128729A patent/TW201211030A/zh unknown
- 2011-08-12 MX MX2013001789A patent/MX2013001789A/es not_active Application Discontinuation
- 2011-08-12 EP EP11757790.8A patent/EP2603481B1/en not_active Not-in-force
- 2011-08-12 ES ES11757790.8T patent/ES2526074T3/es active Active
- 2011-08-12 WO PCT/EP2011/063973 patent/WO2012020131A2/en not_active Ceased
- 2011-08-12 CN CN2011800397167A patent/CN103189337A/zh active Pending
- 2011-08-12 CA CA2806644A patent/CA2806644A1/en not_active Abandoned
- 2011-08-12 JP JP2013523639A patent/JP2013538801A/ja active Pending
-
2014
- 2014-06-27 US US14/317,104 patent/US9227930B2/en not_active Expired - Fee Related
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