JP2013538801A5 - - Google Patents
Download PDFInfo
- Publication number
- 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
Links
- 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
- NLOAUVSKIINYOB-UHFFFAOYSA-N n-[2-[[3-[(3-chlorophenyl)methyl]-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=C1OCCNS(=O)(=O)C=1C=NN(C)C=1 NLOAUVSKIINYOB-UHFFFAOYSA-N 0.000 claims 1
- KTVAGKQXEFHKII-UHFFFAOYSA-N n-[2-[[3-[(3-chlorophenyl)methyl]-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=C1OCCNS(=O)(=O)C1CCC1 KTVAGKQXEFHKII-UHFFFAOYSA-N 0.000 claims 1
- DLLZNULEPWSKCW-UHFFFAOYSA-N n-[2-[[3-[(3-chlorophenyl)methyl]-6-fluoro-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(F)=C1OCCNS(=O)(=O)C1=CN(C)C=N1 DLLZNULEPWSKCW-UHFFFAOYSA-N 0.000 claims 1
- 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
- SXQJELDRGBPMPF-UHFFFAOYSA-N n-[2-[[3-benzyl-2-(methylamino)-2,3-dihydro-1h-inden-5-yl]oxy]ethyl]-1-cyclopropylmethanesulfonamide Chemical compound C1=C2C(CC=3C=CC=CC=3)C(NC)CC2=CC=C1OCCNS(=O)(=O)CC1CC1 SXQJELDRGBPMPF-UHFFFAOYSA-N 0.000 claims 1
- 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
- QEXRCSCQJVUIMZ-UHFFFAOYSA-N n-[2-[[3-benzyl-2-(methylamino)-2,3-dihydro-1h-inden-5-yl]oxy]ethyl]cyclobutanesulfonamide Chemical compound C1=C2C(CC=3C=CC=CC=3)C(NC)CC2=CC=C1OCCNS(=O)(=O)C1CCC1 QEXRCSCQJVUIMZ-UHFFFAOYSA-N 0.000 claims 1
- IVEFFMQEWCUORL-UHFFFAOYSA-N n-[2-[[3-benzyl-6-fluoro-2-(3-hydroxy-3-methylazetidin-1-yl)-2,3-dihydro-1h-inden-5-yl]oxy]ethyl]-n,1-dimethylimidazole-4-sulfonamide Chemical compound C=1N(C)C=NC=1S(=O)(=O)N(C)CCOC(C(=CC=1CC2N3CC(C)(O)C3)F)=CC=1C2CC1=CC=CC=C1 IVEFFMQEWCUORL-UHFFFAOYSA-N 0.000 claims 1
- GGOFPOBAPMHJSK-UHFFFAOYSA-N n-[2-[[3-benzyl-6-fluoro-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)=C(F)C=C2C1 GGOFPOBAPMHJSK-UHFFFAOYSA-N 0.000 claims 1
- FRZCCRAQSGPFAJ-UHFFFAOYSA-N n-[2-[[3-benzyl-6-fluoro-2-(methylamino)-2,3-dihydro-1h-inden-5-yl]oxy]ethyl]-1-cyclopropylmethanesulfonamide Chemical compound C1=C2C(CC=3C=CC=CC=3)C(NC)CC2=CC(F)=C1OCCNS(=O)(=O)CC1CC1 FRZCCRAQSGPFAJ-UHFFFAOYSA-N 0.000 claims 1
- WIFIMYGFHQXXKW-UHFFFAOYSA-N n-[2-[[3-benzyl-6-fluoro-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(F)=C1OCCNS(=O)(=O)C1=CN(C)C=N1 WIFIMYGFHQXXKW-UHFFFAOYSA-N 0.000 claims 1
- PJZDASYLBPYQJF-UHFFFAOYSA-N n-[2-[[3-benzyl-6-fluoro-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(F)=C1OCCNS(=O)(=O)C=1C=NN(C)C=1 PJZDASYLBPYQJF-UHFFFAOYSA-N 0.000 claims 1
- NFOBFVLQHCMQHT-UHFFFAOYSA-N n-[2-[[3-benzyl-6-fluoro-2-(methylamino)-2,3-dihydro-1h-inden-5-yl]oxy]ethyl]cyclobutanesulfonamide Chemical compound C1=C2C(CC=3C=CC=CC=3)C(NC)CC2=CC(F)=C1OCCNS(=O)(=O)C1CCC1 NFOBFVLQHCMQHT-UHFFFAOYSA-N 0.000 claims 1
- AUPZSAIBNIYXRW-UHFFFAOYSA-N n-[2-[[6-fluoro-2-(methylamino)-3-[[3-(trifluoromethyl)phenyl]methyl]-2,3-dihydro-1h-inden-5-yl]oxy]ethyl]-1-methylimidazole-4-sulfonamide Chemical compound C1=C2C(CC=3C=C(C=CC=3)C(F)(F)F)C(NC)CC2=CC(F)=C1OCCNS(=O)(=O)C1=CN(C)C=N1 AUPZSAIBNIYXRW-UHFFFAOYSA-N 0.000 claims 1
- 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
- GWIXZGGJDDAODY-UHFFFAOYSA-N n-[2-[[6-fluoro-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(F)=C1OCCNS(=O)(=O)C=1C=NN(C)C=1 GWIXZGGJDDAODY-UHFFFAOYSA-N 0.000 claims 1
- NXVNDJBDZXZIST-UHFFFAOYSA-N n-[2-[[6-fluoro-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(F)=C1OCCNS(=O)(=O)C1CCC1 NXVNDJBDZXZIST-UHFFFAOYSA-N 0.000 claims 1
- 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
- YCXLZTNRTOAIPD-UHFFFAOYSA-N n-[[2-(azetidin-1-yl)-3-[(3-chlorophenyl)methyl]-2,3-dihydro-1h-inden-5-yl]methyl]-1-cyclopropylmethanesulfonamide Chemical compound ClC1=CC=CC(CC2C3=CC(CNS(=O)(=O)CC4CC4)=CC=C3CC2N2CCC2)=C1 YCXLZTNRTOAIPD-UHFFFAOYSA-N 0.000 claims 1
- 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
- HZPRXRGIEPQRDK-UHFFFAOYSA-N n-[[2-(azetidin-1-yl)-3-[(3-chlorophenyl)methyl]-2,3-dihydro-1h-inden-5-yl]methyl]cyclobutanesulfonamide Chemical compound ClC1=CC=CC(CC2C3=CC(CNS(=O)(=O)C4CCC4)=CC=C3CC2N2CCC2)=C1 HZPRXRGIEPQRDK-UHFFFAOYSA-N 0.000 claims 1
- DPBWQVMUTUPZKD-UHFFFAOYSA-N n-[[2-(azetidin-1-yl)-3-[(3-chlorophenyl)methyl]-6-fluoro-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(Cl)C=CC=4)C=3C=2)N2CCC2)F)=C1 DPBWQVMUTUPZKD-UHFFFAOYSA-N 0.000 claims 1
- 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
- ALJFIANEAZFPRJ-UHFFFAOYSA-N n-[[2-(azetidin-1-yl)-3-[(3-fluorophenyl)methyl]-2,3-dihydro-1h-inden-5-yl]methyl]-1-cyclopropylmethanesulfonamide Chemical compound FC1=CC=CC(CC2C3=CC(CNS(=O)(=O)CC4CC4)=CC=C3CC2N2CCC2)=C1 ALJFIANEAZFPRJ-UHFFFAOYSA-N 0.000 claims 1
- DAGRHNYFGIKNFV-UHFFFAOYSA-N n-[[2-(azetidin-1-yl)-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=C3C(CC=4C=C(F)C=CC=4)C(CC3=CC=2)N2CCC2)=C1 DAGRHNYFGIKNFV-UHFFFAOYSA-N 0.000 claims 1
- 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
- ONIWWPSZQYCMRF-UHFFFAOYSA-N n-[[2-(azetidin-1-yl)-3-[(3-fluorophenyl)methyl]-2,3-dihydro-1h-inden-5-yl]methyl]cyclobutanesulfonamide Chemical compound FC1=CC=CC(CC2C3=CC(CNS(=O)(=O)C4CCC4)=CC=C3CC2N2CCC2)=C1 ONIWWPSZQYCMRF-UHFFFAOYSA-N 0.000 claims 1
- ZGQMLVHJQJZGFV-UHFFFAOYSA-N n-[[2-(azetidin-1-yl)-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)NCC1=CC=C(CC(C2CC=3C=C(C=CC=3)C(F)(F)F)N3CCC3)C2=C1 ZGQMLVHJQJZGFV-UHFFFAOYSA-N 0.000 claims 1
- 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
- TXXMWGMJLGUTEH-UHFFFAOYSA-N n-[[2-(azetidin-1-yl)-3-benzyl-2,3-dihydro-1h-inden-5-yl]methyl]-1-methylimidazole-4-sulfonamide Chemical compound CN1C=NC(S(=O)(=O)NCC=2C=C3C(CC=4C=CC=CC=4)C(CC3=CC=2)N2CCC2)=C1 TXXMWGMJLGUTEH-UHFFFAOYSA-N 0.000 claims 1
- IWDGWKUCNREKSG-UHFFFAOYSA-N n-[[2-(azetidin-1-yl)-3-benzyl-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=CC=CC=3)N3CCC3)C2=C1 IWDGWKUCNREKSG-UHFFFAOYSA-N 0.000 claims 1
- IJGJKHBOJKKDRA-UHFFFAOYSA-N n-[[2-(azetidin-1-yl)-3-benzyl-2,3-dihydro-1h-inden-5-yl]methyl]cyclobutanesulfonamide Chemical compound C1CCC1S(=O)(=O)NCC(C=C12)=CC=C1CC(N1CCC1)C2CC1=CC=CC=C1 IJGJKHBOJKKDRA-UHFFFAOYSA-N 0.000 claims 1
- 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
- JDTXSWGTPIHSII-UHFFFAOYSA-N n-[[2-(azetidin-1-yl)-6-fluoro-3-[(3-fluorophenyl)methyl]-2,3-dihydro-1h-inden-5-yl]methyl]cyclobutanesulfonamide Chemical compound FC1=CC=CC(CC2C3=CC(CNS(=O)(=O)C4CCC4)=C(F)C=C3CC2N2CCC2)=C1 JDTXSWGTPIHSII-UHFFFAOYSA-N 0.000 claims 1
- 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
- VAHDJMJHIBKNDN-UHFFFAOYSA-N n-[[3-[(3-chlorophenyl)methyl]-2-(methylamino)-2,3-dihydro-1h-inden-5-yl]methyl]-1-methylpyrazole-4-sulfonamide Chemical compound C1=C2C(CC=3C=C(Cl)C=CC=3)C(NC)CC2=CC=C1CNS(=O)(=O)C=1C=NN(C)C=1 VAHDJMJHIBKNDN-UHFFFAOYSA-N 0.000 claims 1
- DPKZMTOXLILUIW-UHFFFAOYSA-N n-[[3-[(3-chlorophenyl)methyl]-2-(methylamino)-2,3-dihydro-1h-inden-5-yl]methyl]cyclobutanesulfonamide Chemical compound C1=C2C(CC=3C=C(Cl)C=CC=3)C(NC)CC2=CC=C1CNS(=O)(=O)C1CCC1 DPKZMTOXLILUIW-UHFFFAOYSA-N 0.000 claims 1
- 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
- XPRYPBWNUHQJFW-UHFFFAOYSA-N n-[[3-[(3-chlorophenyl)methyl]-6-fluoro-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(F)=C1CNS(=O)(=O)C1=CN(C)C=N1 XPRYPBWNUHQJFW-UHFFFAOYSA-N 0.000 claims 1
- WRFOONHOLWDXSX-UHFFFAOYSA-N n-[[3-[(3-chlorophenyl)methyl]-6-fluoro-2-(methylamino)-2,3-dihydro-1h-inden-5-yl]methyl]-1-methylpyrazole-4-sulfonamide Chemical compound C1=C2C(CC=3C=C(Cl)C=CC=3)C(NC)CC2=CC(F)=C1CNS(=O)(=O)C=1C=NN(C)C=1 WRFOONHOLWDXSX-UHFFFAOYSA-N 0.000 claims 1
- FGHPHADVMQZBAY-UHFFFAOYSA-N n-[[3-[(3-chlorophenyl)methyl]-6-fluoro-2-(methylamino)-2,3-dihydro-1h-inden-5-yl]methyl]cyclobutanesulfonamide Chemical compound C1=C2C(CC=3C=C(Cl)C=CC=3)C(NC)CC2=CC(F)=C1CNS(=O)(=O)C1CCC1 FGHPHADVMQZBAY-UHFFFAOYSA-N 0.000 claims 1
- YRUDSQULOGFWKD-UHFFFAOYSA-N n-[[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=C1CNS(=O)(=O)C1=CN(C)C=N1 YRUDSQULOGFWKD-UHFFFAOYSA-N 0.000 claims 1
- 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
- SMPRFHRTEWPVLV-UHFFFAOYSA-N n-[[3-[(3-fluorophenyl)methyl]-2-(methylamino)-2,3-dihydro-1h-inden-5-yl]methyl]cyclobutanesulfonamide Chemical compound C1=C2C(CC=3C=C(F)C=CC=3)C(NC)CC2=CC=C1CNS(=O)(=O)C1CCC1 SMPRFHRTEWPVLV-UHFFFAOYSA-N 0.000 claims 1
- VHWPJWIRGDFSRY-UHFFFAOYSA-N n-[[3-benzyl-2-(methylamino)-2,3-dihydro-1h-inden-5-yl]methyl]-1-cyclopropylmethanesulfonamide Chemical compound C1=C2C(CC=3C=CC=CC=3)C(NC)CC2=CC=C1CNS(=O)(=O)CC1CC1 VHWPJWIRGDFSRY-UHFFFAOYSA-N 0.000 claims 1
- 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
- NBBYIAUZPNJZTB-UHFFFAOYSA-N n-[[3-benzyl-6-fluoro-2-(methylamino)-2,3-dihydro-1h-inden-5-yl]methyl]-1-cyclopropylmethanesulfonamide Chemical compound C1=C2C(CC=3C=CC=CC=3)C(NC)CC2=CC(F)=C1CNS(=O)(=O)CC1CC1 NBBYIAUZPNJZTB-UHFFFAOYSA-N 0.000 claims 1
- JECCAYNKSCZQNF-UHFFFAOYSA-N n-[[3-benzyl-6-fluoro-2-(methylamino)-2,3-dihydro-1h-inden-5-yl]methyl]-1-methylimidazole-4-sulfonamide Chemical compound C1=C2C(CC=3C=CC=CC=3)C(NC)CC2=CC(F)=C1CNS(=O)(=O)C1=CN(C)C=N1 JECCAYNKSCZQNF-UHFFFAOYSA-N 0.000 claims 1
- CSCXRAYDHNGRLU-UHFFFAOYSA-N n-[[3-benzyl-6-fluoro-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(F)=C1CNS(=O)(=O)C=1C=NN(C)C=1 CSCXRAYDHNGRLU-UHFFFAOYSA-N 0.000 claims 1
- IZSOMMMXPDSFDW-UHFFFAOYSA-N n-[[3-benzyl-6-fluoro-2-(methylamino)-2,3-dihydro-1h-inden-5-yl]methyl]cyclobutanesulfonamide Chemical compound C1=C2C(CC=3C=CC=CC=3)C(NC)CC2=CC(F)=C1CNS(=O)(=O)C1CCC1 IZSOMMMXPDSFDW-UHFFFAOYSA-N 0.000 claims 1
- FJIRCQOIOWQAHJ-UHFFFAOYSA-N n-[[6-fluoro-2-(methylamino)-3-[[3-(trifluoromethyl)phenyl]methyl]-2,3-dihydro-1h-inden-5-yl]methyl]-1-methylimidazole-4-sulfonamide Chemical compound C1=C2C(CC=3C=C(C=CC=3)C(F)(F)F)C(NC)CC2=CC(F)=C1CNS(=O)(=O)C1=CN(C)C=N1 FJIRCQOIOWQAHJ-UHFFFAOYSA-N 0.000 claims 1
- 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
- HOSPKBLSADUQSV-UHFFFAOYSA-N n-[[6-fluoro-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(F)=C1CNS(=O)(=O)C=1C=NN(C)C=1 HOSPKBLSADUQSV-UHFFFAOYSA-N 0.000 claims 1
- JVZRGLVMOSIDKQ-UHFFFAOYSA-N n-[[6-fluoro-3-[(3-fluorophenyl)methyl]-2-(methylamino)-2,3-dihydro-1h-inden-5-yl]methyl]cyclobutanesulfonamide Chemical compound C1=C2C(CC=3C=C(F)C=CC=3)C(NC)CC2=CC(F)=C1CNS(=O)(=O)C1CCC1 JVZRGLVMOSIDKQ-UHFFFAOYSA-N 0.000 claims 1
- LPKUYALDGULAMJ-UHFFFAOYSA-N 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=C(C3CN(C3)S(=O)(=O)C=3N=CN(C)C=3)C=C2C1CC1=CC=CC(C(F)(F)F)=C1 LPKUYALDGULAMJ-UHFFFAOYSA-N 0.000 claims 1
- DPFKKXQTJULEFP-UHFFFAOYSA-N 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=C(C3CN(C3)S(=O)(=O)C3=CN(C)N=C3)C=C2C1CC1=CC=CC(C(F)(F)F)=C1 DPFKKXQTJULEFP-UHFFFAOYSA-N 0.000 claims 1
- 230000000926 neurological effect Effects 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 208000020016 psychiatric disease Diseases 0.000 claims 1
- 125000006413 ring segment Chemical group 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US37359010P | 2010-08-13 | 2010-08-13 | |
| US61/373,590 | 2010-08-13 | ||
| PCT/EP2011/063973 WO2012020131A2 (en) | 2010-08-13 | 2011-08-12 | Aminoindane derivatives, pharmaceutical compositions containing them, and their use in therapy |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2013538801A JP2013538801A (ja) | 2013-10-17 |
| JP2013538801A5 true JP2013538801A5 (enExample) | 2014-09-25 |
Family
ID=44653266
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013523639A Pending JP2013538801A (ja) | 2010-08-13 | 2011-08-12 | アミノインダン誘導体、それを含有する医薬組成物および治療におけるそれの使用 |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US8846743B2 (enExample) |
| EP (1) | EP2603481B1 (enExample) |
| JP (1) | JP2013538801A (enExample) |
| CN (1) | CN103189337A (enExample) |
| CA (1) | CA2806644A1 (enExample) |
| ES (1) | ES2526074T3 (enExample) |
| MX (1) | MX2013001789A (enExample) |
| TW (1) | TW201211030A (enExample) |
| WO (1) | WO2012020131A2 (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX2010010773A (es) | 2008-04-01 | 2011-04-11 | Abbott Gmbh & Co Kg | Tetrahidroisoquinolinas, composiciones farmaceuticas que las contienen y su uso en terapia. |
| AR075442A1 (es) | 2009-02-16 | 2011-03-30 | Abbott Gmbh & Co Kg | Derivados de aminotetralina, composiciones farmaceuticas que las contienen y sus usos en terapia |
| US9045459B2 (en) | 2010-08-13 | 2015-06-02 | AbbVie Deutschland GmbH & Co. KG | Phenalkylamine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US8846743B2 (en) | 2010-08-13 | 2014-09-30 | Abbott Laboratories | Aminoindane derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9051280B2 (en) | 2010-08-13 | 2015-06-09 | AbbVie Deutschland GmbH & Co. KG | Tetraline and indane derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US8877794B2 (en) | 2010-08-13 | 2014-11-04 | Abbott Laboratories | Phenalkylamine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US8883839B2 (en) | 2010-08-13 | 2014-11-11 | Abbott Laboratories | Tetraline and indane derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9309200B2 (en) | 2011-05-12 | 2016-04-12 | AbbVie Deutschland GmbH & Co. KG | Benzazepine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US8853196B2 (en) | 2011-08-05 | 2014-10-07 | AbbVie Deutschland GmbH & Co. KG | Aminochromane, aminothiochromane and amino-1,2,3,4-tetrahydroquinoline derivatives, pharmaceutical compositions containing them, and their use in therapy |
| MX2014006004A (es) * | 2011-11-18 | 2015-04-16 | Abbvie Deutschland | Derivados de aminobenzociclohepteno, aminotetralina, aminoindano y fenalcilamina n-sustituidas, composiciones farmaceuticas que los contienen, y su uso en terapia. |
| US9365512B2 (en) | 2012-02-13 | 2016-06-14 | AbbVie Deutschland GmbH & Co. KG | Isoindoline derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9227901B2 (en) | 2012-07-05 | 2016-01-05 | Abbvie Inc. | Process for preparing bicyclic amine derivatives |
| US9650334B2 (en) | 2013-03-15 | 2017-05-16 | Abbvie Inc. | Pyrrolidine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9656955B2 (en) | 2013-03-15 | 2017-05-23 | Abbvie Inc. | Pyrrolidine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| CN104418775B (zh) * | 2013-09-05 | 2017-01-18 | 中国科学院大连化学物理研究所 | 一种钯催化氨基醇的不对称氢解合成手性胺的方法 |
| MX2016004934A (es) | 2013-10-17 | 2016-12-20 | Abbvie Deutschland | Derivados de aminotetralina y aminoindano, composiciones farmaceuticas que los contienen, y su uso en terapia. |
| EP3057960B1 (en) | 2013-10-17 | 2019-02-27 | AbbVie Deutschland GmbH & Co. KG | Aminochromane, aminothiochromane and amino-1,2,3,4-tetrahydroquinoline derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9550754B2 (en) * | 2014-09-11 | 2017-01-24 | AbbVie Deutschland GmbH & Co. KG | 4,5-dihydropyrazole derivatives, pharmaceutical compositions containing them, and their use in therapy |
| LT3319959T (lt) | 2015-07-06 | 2021-12-27 | Alkermes, Inc. | Histono deacetilazės hetero-halogeno inhibitoriai |
| WO2017007755A1 (en) | 2015-07-06 | 2017-01-12 | Rodin Therapeutics, Inc. | Heterobicyclic n-aminophenyl-amides as inhibitors of histone deacetylase |
| US10793567B2 (en) | 2017-01-11 | 2020-10-06 | Rodin Therapeutics, Inc. | Bicyclic inhibitors of histone deacetylase |
| EA039417B1 (ru) | 2017-08-07 | 2022-01-25 | Родин Терапеутикс, Инк. | Бициклические ингибиторы гистондеацетилазы |
| CN114276243A (zh) * | 2021-12-13 | 2022-04-05 | 浙江九洲药业股份有限公司 | 一种洛索洛芬及其类似物的合成方法 |
Family Cites Families (128)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3867391A (en) | 1973-08-09 | 1975-02-18 | Pfizer | Cyclic n-substituted derivatives of 1,4-benzene disulphonamide |
| SE8004002L (sv) | 1980-05-29 | 1981-11-30 | Arvidsson Folke Lars Erik | Terapeutiskt anvendbara tetralinderivat |
| EP0091241B1 (en) | 1982-04-02 | 1988-12-28 | Takeda Chemical Industries, Ltd. | Condensed pyrrolinone derivatives, and their production |
| US4789678A (en) | 1986-08-25 | 1988-12-06 | Hoechst-Roussel Pharmaceuticals, Inc. | Memory enhancing α-alkyl-4-amino-3-quinolinemethanols and 1-(4-aralkylamino-3-quinolinyl)alkanones and related compounds |
| US4927838A (en) | 1987-07-10 | 1990-05-22 | Hoffman-La Roche Inc. | Pyridine compounds which are useful in treating a disease state characterized by an excess of platelet activating factors |
| ZA885824B (en) | 1987-08-14 | 1989-04-26 | Merrell Dow Pharma | Novel antidepressants |
| US5300523A (en) | 1988-07-28 | 1994-04-05 | Bayer Aktiengesellschaft | Substituted aminomethyltetralins and their heterocyclic analogues |
| US5545755A (en) | 1989-05-31 | 1996-08-13 | The Upjohn Company | Therapeutically useful 2-aminotetralin derivatives |
| WO1992006967A1 (en) | 1990-10-12 | 1992-04-30 | The Upjohn Company | Therapeutically useful 2-aminotetralin derivatives |
| DE69032725T2 (de) | 1989-05-31 | 1999-04-08 | Pharmacia & Upjohn Co., Kalamazoo, Mich. | ZNS-wirksame 8-Heterocyclyl-2-aminotetralin Derivate |
| US5071875A (en) | 1989-09-25 | 1991-12-10 | Northwestern University | Substituted 2-amidotetralins as melatonin agonists and antagonists |
| WO1992019234A2 (en) | 1991-04-26 | 1992-11-12 | The Upjohn Company | Method of treating/preventing substance abuse using 1-alkyl-5(substituted oxy)-2-aminotetralins |
| JPH05213884A (ja) | 1991-06-14 | 1993-08-24 | Upjohn Co:The | 新規な４−アミノキノリン類およびこれを有効成分とする高血圧・鬱血性心不全の予防・治療剤 |
| GB9127306D0 (en) | 1991-12-23 | 1992-02-19 | Boots Co Plc | Therapeutic agents |
| MY115155A (en) | 1993-09-09 | 2003-04-30 | Upjohn Co | Substituted oxazine and thiazine oxazolidinone antimicrobials. |
| EP1019385B1 (en) | 1995-09-15 | 2004-01-14 | PHARMACIA & UPJOHN COMPANY | Aminoaryl oxazolidinone n-oxides |
| SI1014966T1 (sl) | 1996-05-31 | 2006-10-31 | Allelix Neuroscience Inc | Zdravilo za zdravljenje nevroloskih in nevripsihiatricnih bolezni |
| US6083986A (en) * | 1996-07-26 | 2000-07-04 | Icagen, Inc. | Potassium channel inhibitors |
| US6057357A (en) * | 1997-04-30 | 2000-05-02 | Warner-Lambert Company | Peripherally selective kappa opioid agonists |
| AU7552198A (en) | 1997-06-11 | 1998-12-30 | Sankyo Company Limited | Benzylamine derivatives |
| US6060491A (en) | 1997-06-19 | 2000-05-09 | Dupont Pharmaceuticals | 6-membered aromatics as factor Xa inhibitors |
| US20030220234A1 (en) | 1998-11-02 | 2003-11-27 | Selvaraj Naicker | Deuterated cyclosporine analogs and their use as immunodulating agents |
| US6197798B1 (en) | 1998-07-21 | 2001-03-06 | Novartis Ag | Amino-benzocycloalkane derivatives |
| TW555757B (en) * | 1998-07-31 | 2003-10-01 | Akzo Nobel Nv | Aminomethylcarboxylic acid derivatives |
| DE69922676T2 (de) | 1998-10-07 | 2005-12-15 | Ortho-Mcneil Pharmaceutical, Inc. | N-aralkylaminotetraline als neuropeptid-y-y5-rezeptorliganden |
| US6958333B1 (en) | 1999-07-26 | 2005-10-25 | Banyu Pharmaceutical Co., Ltd. | Biarylurea derivatives |
| MXPA02000927A (es) | 1999-07-28 | 2003-07-14 | Johnson & Johnson | Amina y derivados de amida como ligandos para el receptor del neuropeptido y y5 utiles en el tratamiento de obesidad y otros trastornos. |
| GB9918037D0 (en) | 1999-07-30 | 1999-09-29 | Biochemie Gmbh | Organic compounds |
| US6426364B1 (en) | 1999-11-01 | 2002-07-30 | Nps Allelix Corp. | Diaryl-enynes |
| EP1240147A1 (en) | 1999-12-21 | 2002-09-18 | Icagen, Inc. | Potassium channel inhibitors |
| JP4850332B2 (ja) | 2000-10-18 | 2012-01-11 | 東京エレクトロン株式会社 | デュアルダマシン構造のエッチング方法 |
| DE60205234T2 (de) | 2001-03-27 | 2006-05-24 | Actelion Pharmaceuticals Ltd. | 1,2,3,4-tetrahydroisochinolin-derivate als urotensin ii rezeptor-antagonisten |
| AU2756602A (en) | 2001-04-25 | 2002-10-31 | Pfizer Products Inc. | Methods and kits for treating depression or preventing deterioration of cognitive function |
| US6831193B2 (en) | 2001-05-18 | 2004-12-14 | Abbott Laboratories | Trisubstituted-N-[(1S)-1,2,3,4-Tetrahydro-1-naphthalenyl]benzamides which inhibit P2X3 and P2X2/3 containing receptors |
| ATE305917T1 (de) | 2001-08-16 | 2005-10-15 | Pfizer Prod Inc | Difluormethylen aromatische ether und ihre verwendung als inhibitoren des glycin-typ-1- transporters |
| DE10149370A1 (de) | 2001-10-06 | 2003-04-10 | Merck Patent Gmbh | Pyrazolderivate |
| AU2002343557A1 (en) | 2001-11-21 | 2003-06-10 | Pharmacia And Upjohn Company | Substituted aryl 1,4-pyrazine derivatives |
| MXPA04005989A (es) | 2001-12-20 | 2004-09-27 | Lundbeck & Co As H | Derivados de ariloxifenilo y arilsulfanilfenilo. |
| GB0130696D0 (en) | 2001-12-21 | 2002-02-06 | Smithkline Beecham Plc | Chemical Compounds |
| DE60322186D1 (de) | 2002-02-12 | 2008-08-28 | Organon Nv | 1-arylsulfonyl-3-substituierte indol und indolinederivate verwendbar zur behandlung von erkrankungen des zentralnervensystem |
| DE10210779A1 (de) | 2002-03-12 | 2003-10-09 | Merck Patent Gmbh | Cyclische Amide |
| DE10217006A1 (de) | 2002-04-16 | 2003-11-06 | Merck Patent Gmbh | Substituierte Indole |
| FR2838739B1 (fr) | 2002-04-19 | 2004-05-28 | Sanofi Synthelabo | Derives de n-[phenyl(piperidin-2-yl)methyl)benzamide, leur preparation et leur application en therapeutique |
| US6984647B2 (en) | 2002-05-17 | 2006-01-10 | Janssen Pharmaceutica N.V. | Aminotetralin-derived urea modulators of vanilloid VR1 receptor |
| DE60330485D1 (de) | 2002-07-15 | 2010-01-21 | Merck & Co Inc | Zur behandlung von diabetes |
| FR2842804B1 (fr) | 2002-07-29 | 2004-09-03 | Sanofi Synthelabo | Derives de n-[phenyl(piperidin-2-yl)methyl]benzamide, leur preparation et leur application en therapeutique |
| FR2842805A1 (fr) | 2002-07-29 | 2004-01-30 | Sanofi Synthelabo | Derives de n-[phenyl(piperidin-2-yl)methyl]benzamide,leur preparation et leur application et therapeutique |
| US20040152741A1 (en) | 2002-09-09 | 2004-08-05 | Nps Allelix Corporation | Arylglycine derivatives and their use as glycine transport inhibitors |
| US7084154B2 (en) | 2003-02-11 | 2006-08-01 | Pharmacopeia Drug Disclovery, Inc. | 2-(aminomethyl) arylamide analgesics |
| BRPI0407543A (pt) | 2003-02-17 | 2006-02-14 | Hoffmann La Roche | derivados de piperidina-benzenossulfonamida |
| EP1613597B1 (en) | 2003-03-07 | 2007-11-07 | Eli Lilly and Company | 6-substituted nicotinamide derivatives as opioid receptor antagonists |
| DE10315570A1 (de) | 2003-04-05 | 2004-10-14 | Merck Patent Gmbh | Triazolderivate |
| CN100439330C (zh) | 2003-04-30 | 2008-12-03 | H.隆德贝克有限公司 | 芳族羟苯基和芳族硫基苯基衍生物 |
| JP2004359633A (ja) | 2003-06-06 | 2004-12-24 | Bayer Cropscience Ag | イソインドリノン誘導体の殺虫剤としての利用 |
| GB0314476D0 (en) | 2003-06-20 | 2003-07-23 | Glaxo Group Ltd | Compounds |
| GB0314479D0 (en) | 2003-06-20 | 2003-07-23 | Glaxo Group Ltd | Compounds |
| GB0314478D0 (en) | 2003-06-20 | 2003-07-23 | Glaxo Group Ltd | Compounds |
| AU2004259739A1 (en) | 2003-07-23 | 2005-02-03 | Wyeth | Sulfonyldihydro- benzimidazolone compounds as 5-hydroxytryptamine-6 ligands |
| AU2004263306B2 (en) | 2003-08-11 | 2010-04-22 | F. Hoffmann-La Roche Ag | Piperazine with or-substituted phenyl group and their use as GLYT1 inhibitors |
| JP4563387B2 (ja) | 2003-09-09 | 2010-10-13 | エフ．ホフマン−ラ ロシュ アーゲー | 精神病の処置のためのグリシン取り込み阻害剤としての１−ベンゾイル−ピペラジン誘導体 |
| DK1663232T3 (da) | 2003-09-09 | 2008-02-04 | Hoffmann La Roche | Benzimidazolderivater som human chymase-inhibitorer |
| FR2861076B1 (fr) | 2003-10-17 | 2006-01-06 | Sanofi Synthelabo | Derives de n-heterocyclymethylbenzamide, leur preparation et leur application en therapeutique |
| FR2861073B1 (fr) | 2003-10-17 | 2006-01-06 | Sanofi Synthelabo | Derives de n-[heteroaryl(piperidin-2-yl)methyl]benzamide, leur preparation et leur application en therapeutique |
| FR2861074B1 (fr) | 2003-10-17 | 2006-04-07 | Sanofi Synthelabo | Derives de n-[phenyl(piperidin-2-yl)methyl]benzamide, leur preparation et leur application en therapeutique |
| FR2861071B1 (fr) | 2003-10-17 | 2006-01-06 | Sanofi Synthelabo | Derives de n-[phenyl(alkylpiperidin-2-yl) methyl]benzamide, leur prepartation et leur application en therapeutique |
| FR2861070B1 (fr) | 2003-10-17 | 2006-01-06 | Sanofi Synthelabo | Derives de n-[phenyl(pyrrolidin-2-yl)methyl]benzamide et n-[(azepan-2-yl)phenylmethyl]benzamide, leur preparation et leur application en therapeutique |
| MXPA06004305A (es) | 2003-10-23 | 2006-06-05 | Hoffmann La Roche | Derivados de triaza-espiropiperidina para uso como inhibidores del transformador de glicina 1 en tratamiento de enfermedades neurologicas y neuropsiquiatricas. |
| US20070105902A1 (en) | 2003-11-12 | 2007-05-10 | Lindsley Craig W | 4-Phenyl piperdine sulfonyl glycine transporter inhibitors |
| GB0326840D0 (en) | 2003-11-18 | 2003-12-24 | Glaxo Group Ltd | Compounds |
| WO2005058317A1 (en) | 2003-12-18 | 2005-06-30 | Glaxo Group Limited | Glycine transporter-1 inhibirors |
| GB0329362D0 (en) | 2003-12-18 | 2004-01-21 | Glaxo Group Ltd | Compounds |
| WO2005058885A2 (en) | 2003-12-18 | 2005-06-30 | Glaxo Group Limited | Piperidine derivatives and their use as glycine transporter inhibitors |
| EP1737850B1 (en) | 2004-04-19 | 2007-10-03 | Symed Labs Limited | A novel process for the preparation of linezolid and related compounds |
| DE102004030099A1 (de) | 2004-06-22 | 2006-01-12 | Grünenthal GmbH | Gesättigte und ungesättigte 3-Pyridyl-benzocycloalkylmethyl-amine als Serotonin- und/oder Noradrenalin-Reuptake-Hemmer und/oder µ-Opioidrezeptor-Modulatoren |
| US7429661B2 (en) | 2004-07-20 | 2008-09-30 | Symed Labs Limited | Intermediates for linezolid and related compounds |
| EP1793359A4 (en) | 2004-08-31 | 2010-05-19 | Panasonic Corp | CONTENT PROCESSING SENDING DEVICE, METHOD THEREFOR AND PROGRAM |
| US20060074105A1 (en) | 2004-09-20 | 2006-04-06 | Serenex, Inc. | Substituted quinoline and quinazoline inhibitors of quinone reductase 2 |
| JP2008514702A (ja) | 2004-09-29 | 2008-05-08 | エーエムアール テクノロジー インコーポレイテッド | 新規シクロスポリン類似体およびそれらの薬学的使用 |
| CA2583967C (en) | 2004-10-14 | 2013-07-23 | Abbott Gmbh & Co. Kg | 6-amino(aza)indane compounds suitable for treating disorders that respond to modulation of the dopamine d3 receptor |
| CA2590316A1 (en) | 2004-12-15 | 2006-06-22 | F. Hoffmann-La Roche Ag | Bi- and tricyclic substituted phenyl methanones as glycine transporter i (glyt-1) inhibitors for the treatment of alzheimer's disease |
| DE102005000666B3 (de) | 2005-01-04 | 2006-10-05 | Sanofi-Aventis Deutschland Gmbh | Sulfonylpyrrolidine, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| CN101119968B (zh) | 2005-02-07 | 2011-08-31 | 弗·哈夫曼-拉罗切有限公司 | 作为甘氨酸转运蛋白1抑制剂的杂环取代的苯基甲酮衍生物 |
| WO2006102760A1 (en) | 2005-04-01 | 2006-10-05 | Methylgene Inc. | Inhibitors of histone deacetylase |
| WO2006121767A2 (en) | 2005-05-06 | 2006-11-16 | Apath, Llc | 4-aminoquinoline compounds for treating virus-related conditions |
| TW200716636A (en) | 2005-05-31 | 2007-05-01 | Speedel Experimenta Ag | Heterocyclic spiro-compounds |
| ZA200800440B (en) | 2005-07-15 | 2009-12-30 | Amr Technology Inc | Aryl-and heteroaryl-substituted tetrahydrobenzazepines and use thereof to block reuptake of norepinephrine, dopamine, and serotonin |
| US7514068B2 (en) | 2005-09-14 | 2009-04-07 | Concert Pharmaceuticals Inc. | Biphenyl-pyrazolecarboxamide compounds |
| AU2006320423B2 (en) | 2005-12-01 | 2012-06-21 | Elan Pharmaceuticals, Inc. | 5-(arylsulfonyl)-pyrazolopiperidines |
| US7592461B2 (en) | 2005-12-21 | 2009-09-22 | Bristol-Myers Squibb Company | Indane modulators of glucocorticoid receptor, AP-1, and/or NF-κB activity and use thereof |
| JP2009539884A (ja) | 2006-06-12 | 2009-11-19 | メルク フロスト カナダ リミテツド | ステアロイル−コエンザイムａデルタ−９デサチュラーゼのインヒビターとしてのアゼチジン誘導体 |
| GB0619176D0 (en) | 2006-09-29 | 2006-11-08 | Lectus Therapeutics Ltd | Ion channel modulators & uses thereof |
| WO2008038841A1 (en) | 2006-09-30 | 2008-04-03 | Japan Tobacco Inc. | Thiadiazolone derivative and use thereof |
| US8796267B2 (en) | 2006-10-23 | 2014-08-05 | Concert Pharmaceuticals, Inc. | Oxazolidinone derivatives and methods of use |
| KR101222412B1 (ko) | 2007-02-15 | 2013-01-15 | 에프. 호프만-라 로슈 아게 | Ｔａａｒ1 리간드로서의 2-아미노옥사졸린 |
| KR20100012031A (ko) | 2007-04-19 | 2010-02-04 | 콘서트 파마슈티컬즈, 인크. | 중수소화된 모르폴리닐 화합물 |
| US7531685B2 (en) | 2007-06-01 | 2009-05-12 | Protia, Llc | Deuterium-enriched oxybutynin |
| CN101679295A (zh) | 2007-06-06 | 2010-03-24 | 帝斯曼知识产权资产管理有限公司 | 新颖的被5-取代的乙内酰脲 |
| US8420670B2 (en) | 2007-08-22 | 2013-04-16 | Abbott Laboratories | 4-benzylaminoquinolines, pharmaceutical compositions containing them, and their use in therapy |
| US20090131485A1 (en) | 2007-09-10 | 2009-05-21 | Concert Pharmaceuticals, Inc. | Deuterated pirfenidone |
| US20090118238A1 (en) | 2007-09-17 | 2009-05-07 | Protia, Llc | Deuterium-enriched alendronate |
| US20090088416A1 (en) | 2007-09-26 | 2009-04-02 | Protia, Llc | Deuterium-enriched lapaquistat |
| US20090082471A1 (en) | 2007-09-26 | 2009-03-26 | Protia, Llc | Deuterium-enriched fingolimod |
| WO2009045476A1 (en) | 2007-10-02 | 2009-04-09 | Concert Pharmaceuticals, Inc. | Pyrimidinedione derivatives |
| WO2009051782A1 (en) | 2007-10-18 | 2009-04-23 | Concert Pharmaceuticals Inc. | Deuterated etravirine |
| US20090105338A1 (en) | 2007-10-18 | 2009-04-23 | Protia, Llc | Deuterium-enriched gabexate mesylate |
| SA08290668B1 (ar) * | 2007-10-25 | 2012-02-12 | شيونوجي آند كو.، ليمتد | مشتقات أمين لها نشاط مضاد لمستقبل npy y5 واستخداماتها |
| US20090131363A1 (en) | 2007-10-26 | 2009-05-21 | Harbeson Scott L | Deuterated darunavir |
| MX2010010773A (es) | 2008-04-01 | 2011-04-11 | Abbott Gmbh & Co Kg | Tetrahidroisoquinolinas, composiciones farmaceuticas que las contienen y su uso en terapia. |
| WO2010020548A1 (en) | 2008-08-20 | 2010-02-25 | F. Hoffmann-La Roche Ag | Glyt1 receptor antagonists |
| CN103396402A (zh) | 2008-09-02 | 2013-11-20 | 赛诺菲-安万特 | 取代的氨基茚满及其类似物以及其医药用途 |
| DE102008047162A1 (de) | 2008-09-15 | 2010-03-25 | Institut Für Solarenergieforschung Gmbh | Rückkontaktsolarzelle mit integrierter Bypass-Diode sowie Herstellungsverfahren hierfür |
| AR075442A1 (es) | 2009-02-16 | 2011-03-30 | Abbott Gmbh & Co Kg | Derivados de aminotetralina, composiciones farmaceuticas que las contienen y sus usos en terapia |
| TW201038569A (en) | 2009-02-16 | 2010-11-01 | Abbott Gmbh & Co Kg | Heterocyclic compounds, pharmaceutical compositions containing them, and their use in therapy |
| EP2246331A1 (en) | 2009-04-24 | 2010-11-03 | Westfälische Wilhelms-Universität Münster | NR2B-selective NMDA-receptor antagonists |
| WO2010138901A1 (en) | 2009-05-29 | 2010-12-02 | Biogen Idec Ma Inc | Carboxylic acid-containing compounds, derivatives thereof, and related methods of use |
| US8846743B2 (en) | 2010-08-13 | 2014-09-30 | Abbott Laboratories | Aminoindane derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US8883839B2 (en) | 2010-08-13 | 2014-11-11 | Abbott Laboratories | Tetraline and indane derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9045459B2 (en) | 2010-08-13 | 2015-06-02 | AbbVie Deutschland GmbH & Co. KG | Phenalkylamine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9051280B2 (en) | 2010-08-13 | 2015-06-09 | AbbVie Deutschland GmbH & Co. KG | Tetraline and indane derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US8877794B2 (en) | 2010-08-13 | 2014-11-04 | Abbott Laboratories | Phenalkylamine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9309200B2 (en) | 2011-05-12 | 2016-04-12 | AbbVie Deutschland GmbH & Co. KG | Benzazepine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US8853196B2 (en) | 2011-08-05 | 2014-10-07 | AbbVie Deutschland GmbH & Co. KG | Aminochromane, aminothiochromane and amino-1,2,3,4-tetrahydroquinoline derivatives, pharmaceutical compositions containing them, and their use in therapy |
| MX2014006004A (es) | 2011-11-18 | 2015-04-16 | Abbvie Deutschland | Derivados de aminobenzociclohepteno, aminotetralina, aminoindano y fenalcilamina n-sustituidas, composiciones farmaceuticas que los contienen, y su uso en terapia. |
| US9365512B2 (en) | 2012-02-13 | 2016-06-14 | AbbVie Deutschland GmbH & Co. KG | Isoindoline derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9650334B2 (en) | 2013-03-15 | 2017-05-16 | Abbvie Inc. | Pyrrolidine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9656955B2 (en) | 2013-03-15 | 2017-05-23 | Abbvie Inc. | Pyrrolidine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| MX2016004934A (es) | 2013-10-17 | 2016-12-20 | Abbvie Deutschland | Derivados de aminotetralina y aminoindano, composiciones farmaceuticas que los contienen, y su uso en terapia. |
| EP3057960B1 (en) | 2013-10-17 | 2019-02-27 | AbbVie Deutschland GmbH & Co. KG | Aminochromane, aminothiochromane and amino-1,2,3,4-tetrahydroquinoline derivatives, pharmaceutical compositions containing them, and their use in therapy |
-
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 WO PCT/EP2011/063973 patent/WO2012020131A2/en not_active Ceased
- 2011-08-12 CA CA2806644A patent/CA2806644A1/en not_active Abandoned
- 2011-08-12 JP JP2013523639A patent/JP2013538801A/ja active Pending
- 2011-08-12 CN CN2011800397167A patent/CN103189337A/zh active Pending
- 2011-08-12 EP EP11757790.8A patent/EP2603481B1/en not_active Not-in-force
- 2011-08-12 MX MX2013001789A patent/MX2013001789A/es not_active Application Discontinuation
- 2011-08-12 ES ES11757790.8T patent/ES2526074T3/es active Active
-
2014
- 2014-06-27 US US14/317,104 patent/US9227930B2/en not_active Expired - Fee Related
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2013538801A5 (enExample) | ||
| RU2440330C2 (ru) | ПРОИЗВОДНЫЕ 4-(2-АМИНО-1-ГИДРОКСИЭТИЛ)ФЕНОЛА, КАК АГОНИСТЫ β2 АДРЕНЕРГИЧЕСКОГО РЕЦЕПТОРА | |
| JP2013538802A5 (enExample) | ||
| ES2675022T3 (es) | Inhibidores de indolamina 2,3-dioxigenasa (IDO) | |
| JP2013536188A5 (enExample) | ||
| RU2015105561A (ru) | Замещенные гетероазепиноны | |
| JP2011517453A5 (enExample) | ||
| PE20141700A1 (es) | Compuestos de 2-(2,4,5-anilino sustituido) pirimidina | |
| PE20081263A1 (es) | DERIVADOS DE 4-(2-AMINO-1-HIDROXIETIL)FENOL COMO AGONISTAS DEL RECEPTOR ß2 ADRENERGICO | |
| JP2013505903A5 (enExample) | ||
| JP2011515398A5 (enExample) | ||
| HRP20120656T1 (hr) | Derivati indazolil amida za liječenje poremećaja posredovanih glukokortikoidnim receptorom | |
| AR072490A1 (es) | 1,2,5- oxadiazoles como inhibidores de indolamina 2,3 dioxigenasa | |
| PE20091446A1 (es) | Derivados de isoxazolo-piridazina | |
| JP2017533968A5 (enExample) | ||
| PE20121050A1 (es) | Compuestos de n-(1-(4-(1h-pirazol-5-il)ftalazin-1-il)piperidin-4-il)-benzamida sustituidos como antagonistas de la trayectoria hedgehog | |
| CO6251317A2 (es) | Procedimiento para sintetizar sal diclorhidrato de ((1s)-1-(((2s) sal diclorhidrato de ((1s)-1-(((2s)-2-(5-(4'-(2-((2s)-1-((2s)-2-((metoxicarbonil)amino)-3-metilbutanoil)-2-pirrolidinil)-1h-imidazol-5-il)-4-bifenilil)-1h-imidazol-2-il)-1-pirrolidinil | |
| PE20061305A1 (es) | Compuestos derivados de fenilacetamidas como inhibidores de proteincinasas | |
| JP2010515750A5 (enExample) | ||
| JP2013538198A5 (enExample) | ||
| JP2017530199A5 (enExample) | ||
| PE20140934A1 (es) | Derivados de pirazol | |
| RU2010143455A (ru) | Имидазохинолины и производные пиримидина в качестве потенциальных модуляторов vegf-стимулируемых ангиогенных процессов | |
| JP2013533253A5 (enExample) | ||
| NZ612544A (en) | Heterocyclic compounds suitable for the treatment of dyslipidemia |