JP2014523901A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2014523901A5 JP2014523901A5 JP2014519057A JP2014519057A JP2014523901A5 JP 2014523901 A5 JP2014523901 A5 JP 2014523901A5 JP 2014519057 A JP2014519057 A JP 2014519057A JP 2014519057 A JP2014519057 A JP 2014519057A JP 2014523901 A5 JP2014523901 A5 JP 2014523901A5
- Authority
- JP
- Japan
- Prior art keywords
- benzamide
- fluoro
- phenyl
- chloro
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 10
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- 150000003839 salts Chemical group 0.000 claims description 6
- 150000004677 hydrates Chemical class 0.000 claims description 5
- BBLXLHYPDOMJMO-UHFFFAOYSA-N 5-(butan-2-ylsulfamoyl)-n-(3,4-difluorophenyl)-2-fluorobenzamide Chemical compound CCC(C)NS(=O)(=O)C1=CC=C(F)C(C(=O)NC=2C=C(F)C(F)=CC=2)=C1 BBLXLHYPDOMJMO-UHFFFAOYSA-N 0.000 claims description 3
- DIBFYUJKGFSYSJ-UHFFFAOYSA-N 5-(cyclohexylsulfamoyl)-n-(3,4-difluorophenyl)-2-fluorobenzamide Chemical compound C1=C(F)C(F)=CC=C1NC(=O)C1=CC(S(=O)(=O)NC2CCCCC2)=CC=C1F DIBFYUJKGFSYSJ-UHFFFAOYSA-N 0.000 claims description 3
- ZSAVPNCDVFOTNN-UHFFFAOYSA-N 5-(cyclopentylsulfamoyl)-n-(3,4-difluorophenyl)-2-fluorobenzamide Chemical compound C1=C(F)C(F)=CC=C1NC(=O)C1=CC(S(=O)(=O)NC2CCCC2)=CC=C1F ZSAVPNCDVFOTNN-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 7
- 229910052801 chlorine Inorganic materials 0.000 claims 7
- 239000000460 chlorine Substances 0.000 claims 7
- 150000002431 hydrogen Chemical class 0.000 claims 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 4
- 241000700721 Hepatitis B virus Species 0.000 claims 4
- 239000000562 conjugate Substances 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 229910052731 fluorine Inorganic materials 0.000 claims 4
- 239000011737 fluorine Substances 0.000 claims 4
- 208000015181 infectious disease Diseases 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 239000000651 prodrug Substances 0.000 claims 4
- 229940002612 prodrug Drugs 0.000 claims 4
- 239000012453 solvate Substances 0.000 claims 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- YTTWDIOCTVIQJQ-UHFFFAOYSA-N 2-bromo-5-(cyclohexylsulfamoyl)-n-phenylbenzamide Chemical compound BrC1=CC=C(S(=O)(=O)NC2CCCCC2)C=C1C(=O)NC1=CC=CC=C1 YTTWDIOCTVIQJQ-UHFFFAOYSA-N 0.000 claims 1
- FNUCPIHCITUGQE-UHFFFAOYSA-N 2-chloro-n-(3-methylphenyl)-5-sulfamoylbenzamide Chemical compound CC1=CC=CC(NC(=O)C=2C(=CC=C(C=2)S(N)(=O)=O)Cl)=C1 FNUCPIHCITUGQE-UHFFFAOYSA-N 0.000 claims 1
- NRRAAVBIZGRKFF-UHFFFAOYSA-N 2-fluoro-5-[(4-fluorophenyl)sulfamoyl]-n-(3-methylphenyl)benzamide Chemical compound CC1=CC=CC(NC(=O)C=2C(=CC=C(C=2)S(=O)(=O)NC=2C=CC(F)=CC=2)F)=C1 NRRAAVBIZGRKFF-UHFFFAOYSA-N 0.000 claims 1
- ZKYVPYFRGZNHJT-UHFFFAOYSA-N 2-fluoro-5-[(4-methoxyphenyl)sulfamoyl]-n-(3-methylphenyl)benzamide Chemical compound C1=CC(OC)=CC=C1NS(=O)(=O)C1=CC=C(F)C(C(=O)NC=2C=C(C)C=CC=2)=C1 ZKYVPYFRGZNHJT-UHFFFAOYSA-N 0.000 claims 1
- MPCMNARIWULMFJ-UHFFFAOYSA-N 2-fluoro-n-(3-fluorophenyl)-5-(furan-2-ylmethylsulfamoyl)benzamide Chemical compound FC1=CC=CC(NC(=O)C=2C(=CC=C(C=2)S(=O)(=O)NCC=2OC=CC=2)F)=C1 MPCMNARIWULMFJ-UHFFFAOYSA-N 0.000 claims 1
- PBAWFYZFSXYUOS-UHFFFAOYSA-N 3-(azepan-1-ylsulfonyl)-n-benzyl-4-chlorobenzamide Chemical compound ClC1=CC=C(C(=O)NCC=2C=CC=CC=2)C=C1S(=O)(=O)N1CCCCCC1 PBAWFYZFSXYUOS-UHFFFAOYSA-N 0.000 claims 1
- KEZNVHQUQCVDAX-UHFFFAOYSA-N 3-(cyclohexylsulfamoyl)-4-methyl-n-phenylbenzamide Chemical compound CC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1S(=O)(=O)NC1CCCCC1 KEZNVHQUQCVDAX-UHFFFAOYSA-N 0.000 claims 1
- WFDUMBOKYBAJST-UHFFFAOYSA-N 3-(cyclopentylsulfamoyl)-4-fluoro-n-(3-methylphenyl)benzamide Chemical compound CC1=CC=CC(NC(=O)C=2C=C(C(F)=CC=2)S(=O)(=O)NC2CCCC2)=C1 WFDUMBOKYBAJST-UHFFFAOYSA-N 0.000 claims 1
- TVUAZFKFLYTZMI-UHFFFAOYSA-N 3-(cyclopentylsulfamoyl)-n-phenylbenzamide Chemical compound C=1C=CC(S(=O)(=O)NC2CCCC2)=CC=1C(=O)NC1=CC=CC=C1 TVUAZFKFLYTZMI-UHFFFAOYSA-N 0.000 claims 1
- DPONBEDTMNFWFV-UHFFFAOYSA-N 3-(diethylsulfamoyl)-n-phenylbenzamide Chemical compound CCN(CC)S(=O)(=O)C1=CC=CC(C(=O)NC=2C=CC=CC=2)=C1 DPONBEDTMNFWFV-UHFFFAOYSA-N 0.000 claims 1
- VFQPLEJOOLNBTH-UHFFFAOYSA-N 3-(furan-2-ylmethylsulfamoyl)-n-phenylbenzamide Chemical compound C=1C=CC(S(=O)(=O)NCC=2OC=CC=2)=CC=1C(=O)NC1=CC=CC=C1 VFQPLEJOOLNBTH-UHFFFAOYSA-N 0.000 claims 1
- KIQGAHCODFLQIZ-UHFFFAOYSA-N 3-[(2-methylphenyl)sulfamoyl]-n-phenylbenzamide Chemical compound CC1=CC=CC=C1NS(=O)(=O)C1=CC=CC(C(=O)NC=2C=CC=CC=2)=C1 KIQGAHCODFLQIZ-UHFFFAOYSA-N 0.000 claims 1
- YVEKYUJVYNNGIM-UHFFFAOYSA-N 3-[(3-methylphenyl)sulfamoyl]-n-phenylbenzamide Chemical compound CC1=CC=CC(NS(=O)(=O)C=2C=C(C=CC=2)C(=O)NC=2C=CC=CC=2)=C1 YVEKYUJVYNNGIM-UHFFFAOYSA-N 0.000 claims 1
- QPCNWXKARWHIMY-UHFFFAOYSA-N 3-[[3-(benzylcarbamoyl)phenyl]sulfonylamino]benzoic acid Chemical compound OC(=O)C1=CC=CC(NS(=O)(=O)C=2C=C(C=CC=2)C(=O)NCC=2C=CC=CC=2)=C1 QPCNWXKARWHIMY-UHFFFAOYSA-N 0.000 claims 1
- SDQANSXWGDCZHL-UHFFFAOYSA-N 3-[benzyl(ethyl)sulfamoyl]-n-(3,4-difluorophenyl)-4-fluorobenzamide Chemical compound C=1C(C(=O)NC=2C=C(F)C(F)=CC=2)=CC=C(F)C=1S(=O)(=O)N(CC)CC1=CC=CC=C1 SDQANSXWGDCZHL-UHFFFAOYSA-N 0.000 claims 1
- MAPCCQHYDIBUOE-UHFFFAOYSA-N 4-chloro-3-(cyclohexylsulfamoyl)-n-(4-fluorophenyl)benzamide Chemical compound C1=CC(F)=CC=C1NC(=O)C1=CC=C(Cl)C(S(=O)(=O)NC2CCCCC2)=C1 MAPCCQHYDIBUOE-UHFFFAOYSA-N 0.000 claims 1
- QDNZYNPFXOYFFH-UHFFFAOYSA-N 4-chloro-n-(3-fluorophenyl)-3-morpholin-4-ylsulfonylbenzamide Chemical compound FC1=CC=CC(NC(=O)C=2C=C(C(Cl)=CC=2)S(=O)(=O)N2CCOCC2)=C1 QDNZYNPFXOYFFH-UHFFFAOYSA-N 0.000 claims 1
- TWVONQXJEQBVIQ-UHFFFAOYSA-N 4-chloro-n-(4-fluorophenyl)-3-piperidin-1-ylsulfonylbenzamide Chemical compound C1=CC(F)=CC=C1NC(=O)C1=CC=C(Cl)C(S(=O)(=O)N2CCCCC2)=C1 TWVONQXJEQBVIQ-UHFFFAOYSA-N 0.000 claims 1
- JSZVDCAAQWXMCQ-UHFFFAOYSA-N 4-chloro-n-phenyl-3-thiomorpholin-4-ylsulfonylbenzamide Chemical compound ClC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1S(=O)(=O)N1CCSCC1 JSZVDCAAQWXMCQ-UHFFFAOYSA-N 0.000 claims 1
- WPMSBSXBLNTLGB-UHFFFAOYSA-N 4-fluoro-3-(furan-2-ylmethylsulfamoyl)-n-(3-methylphenyl)benzamide Chemical compound CC1=CC=CC(NC(=O)C=2C=C(C(F)=CC=2)S(=O)(=O)NCC=2OC=CC=2)=C1 WPMSBSXBLNTLGB-UHFFFAOYSA-N 0.000 claims 1
- ZHWVUVOALLPLDK-UHFFFAOYSA-N 4-fluoro-3-sulfamoyl-n-[3-(trifluoromethyl)phenyl]benzamide Chemical compound C1=C(F)C(S(=O)(=O)N)=CC(C(=O)NC=2C=C(C=CC=2)C(F)(F)F)=C1 ZHWVUVOALLPLDK-UHFFFAOYSA-N 0.000 claims 1
- QSNRCGNYLFXFOX-UHFFFAOYSA-N 4-methyl-n-phenyl-3-piperidin-1-ylsulfonylbenzamide Chemical compound CC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1S(=O)(=O)N1CCCCC1 QSNRCGNYLFXFOX-UHFFFAOYSA-N 0.000 claims 1
- LQSVIKKUGQAEBP-UHFFFAOYSA-N 5-(azepan-1-ylsulfonyl)-n-(3,4-difluorophenyl)-2-fluorobenzamide Chemical compound C1=C(F)C(F)=CC=C1NC(=O)C1=CC(S(=O)(=O)N2CCCCCC2)=CC=C1F LQSVIKKUGQAEBP-UHFFFAOYSA-N 0.000 claims 1
- XOYCHWHQJKTPKY-UHFFFAOYSA-N 5-(benzylsulfamoyl)-2-chloro-n-phenylbenzamide Chemical compound ClC1=CC=C(S(=O)(=O)NCC=2C=CC=CC=2)C=C1C(=O)NC1=CC=CC=C1 XOYCHWHQJKTPKY-UHFFFAOYSA-N 0.000 claims 1
- KYKKHEPFCUUKQU-UHFFFAOYSA-N 5-(benzylsulfamoyl)-n-(3-chloro-4-fluorophenyl)-2-fluorobenzamide Chemical compound C1=C(Cl)C(F)=CC=C1NC(=O)C1=CC(S(=O)(=O)NCC=2C=CC=CC=2)=CC=C1F KYKKHEPFCUUKQU-UHFFFAOYSA-N 0.000 claims 1
- OGAJDFDTOUWQTL-UHFFFAOYSA-N 5-(cycloheptylsulfamoyl)-n-(3,4-difluorophenyl)-2-fluorobenzamide Chemical compound C1=C(F)C(F)=CC=C1NC(=O)C1=CC(S(=O)(=O)NC2CCCCCC2)=CC=C1F OGAJDFDTOUWQTL-UHFFFAOYSA-N 0.000 claims 1
- VWXZMUJTTIZYMN-UHFFFAOYSA-N 5-(cyclopentylsulfamoyl)-2-fluoro-n-(4-fluorophenyl)benzamide Chemical compound C1=CC(F)=CC=C1NC(=O)C1=CC(S(=O)(=O)NC2CCCC2)=CC=C1F VWXZMUJTTIZYMN-UHFFFAOYSA-N 0.000 claims 1
- COIGKRMQVNURRO-UHFFFAOYSA-N 5-(cyclopentylsulfamoyl)-n-(3,5-dichlorophenyl)-2-fluorobenzamide Chemical compound FC1=CC=C(S(=O)(=O)NC2CCCC2)C=C1C(=O)NC1=CC(Cl)=CC(Cl)=C1 COIGKRMQVNURRO-UHFFFAOYSA-N 0.000 claims 1
- XEDMIPPPLRMEDD-UHFFFAOYSA-N 5-(cyclopentylsulfamoyl)-n-(3,5-dimethylphenyl)-2-fluorobenzamide Chemical compound CC1=CC(C)=CC(NC(=O)C=2C(=CC=C(C=2)S(=O)(=O)NC2CCCC2)F)=C1 XEDMIPPPLRMEDD-UHFFFAOYSA-N 0.000 claims 1
- ZHJPAXADDOFOOA-UHFFFAOYSA-N 5-(diethylsulfamoyl)-n-(3,4-difluorophenyl)-2-fluorobenzamide Chemical compound CCN(CC)S(=O)(=O)C1=CC=C(F)C(C(=O)NC=2C=C(F)C(F)=CC=2)=C1 ZHJPAXADDOFOOA-UHFFFAOYSA-N 0.000 claims 1
- SXWOBZCNPAWIMT-UHFFFAOYSA-N 5-[(2-chlorophenyl)methylsulfamoyl]-n-(3,4-difluorophenyl)-2-fluorobenzamide Chemical compound C1=C(F)C(F)=CC=C1NC(=O)C1=CC(S(=O)(=O)NCC=2C(=CC=CC=2)Cl)=CC=C1F SXWOBZCNPAWIMT-UHFFFAOYSA-N 0.000 claims 1
- ANYRROIODVIJMW-UHFFFAOYSA-N 5-[2-(cyclohexen-1-yl)ethylsulfamoyl]-n-(3,5-dimethylphenyl)-2-fluorobenzamide Chemical compound CC1=CC(C)=CC(NC(=O)C=2C(=CC=C(C=2)S(=O)(=O)NCCC=2CCCCC=2)F)=C1 ANYRROIODVIJMW-UHFFFAOYSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- JWGKMOUUSKAEMG-UHFFFAOYSA-N methyl 5-[[[4-chloro-3-(phenylcarbamoyl)phenyl]sulfonylamino]methyl]furan-2-carboxylate Chemical compound O1C(C(=O)OC)=CC=C1CNS(=O)(=O)C1=CC=C(Cl)C(C(=O)NC=2C=CC=CC=2)=C1 JWGKMOUUSKAEMG-UHFFFAOYSA-N 0.000 claims 1
- YTEPBXQPDFTBDV-UHFFFAOYSA-N n-(3,4-difluorophenyl)-2-fluoro-5-(2-phenylethylsulfamoyl)benzamide Chemical compound C1=C(F)C(F)=CC=C1NC(=O)C1=CC(S(=O)(=O)NCCC=2C=CC=CC=2)=CC=C1F YTEPBXQPDFTBDV-UHFFFAOYSA-N 0.000 claims 1
- KVUYYMSVYWAUHA-UHFFFAOYSA-N n-(3,4-difluorophenyl)-4-fluoro-3-[(2-methylcyclohexyl)sulfamoyl]benzamide Chemical compound CC1CCCCC1NS(=O)(=O)C1=CC(C(=O)NC=2C=C(F)C(F)=CC=2)=CC=C1F KVUYYMSVYWAUHA-UHFFFAOYSA-N 0.000 claims 1
- GNYLBBUBZYNWMA-UHFFFAOYSA-N n-(3,4-difluorophenyl)-5-(dipropylsulfamoyl)-2-fluorobenzamide Chemical compound CCCN(CCC)S(=O)(=O)C1=CC=C(F)C(C(=O)NC=2C=C(F)C(F)=CC=2)=C1 GNYLBBUBZYNWMA-UHFFFAOYSA-N 0.000 claims 1
- RNVYVZZFNFIOGY-UHFFFAOYSA-N n-(3,5-dichlorophenyl)-2-fluoro-5-(furan-2-ylmethylsulfamoyl)benzamide Chemical compound FC1=CC=C(S(=O)(=O)NCC=2OC=CC=2)C=C1C(=O)NC1=CC(Cl)=CC(Cl)=C1 RNVYVZZFNFIOGY-UHFFFAOYSA-N 0.000 claims 1
- SQXYIAWQRSLCGK-UHFFFAOYSA-N n-(3-chloro-4-fluorophenyl)-2-fluoro-5-(furan-2-ylmethylsulfamoyl)benzamide Chemical compound C1=C(Cl)C(F)=CC=C1NC(=O)C1=CC(S(=O)(=O)NCC=2OC=CC=2)=CC=C1F SQXYIAWQRSLCGK-UHFFFAOYSA-N 0.000 claims 1
- GGBVCFRVKITRFL-UHFFFAOYSA-N n-(3-chlorophenyl)-2-fluoro-5-(2-phenylethylsulfamoyl)benzamide Chemical compound FC1=CC=C(S(=O)(=O)NCCC=2C=CC=CC=2)C=C1C(=O)NC1=CC=CC(Cl)=C1 GGBVCFRVKITRFL-UHFFFAOYSA-N 0.000 claims 1
- NPEYKKPRQOFFDQ-UHFFFAOYSA-N n-(3-chlorophenyl)-4-fluoro-3-(pyridin-3-ylmethylsulfamoyl)benzamide Chemical compound FC1=CC=C(C(=O)NC=2C=C(Cl)C=CC=2)C=C1S(=O)(=O)NCC1=CC=CN=C1 NPEYKKPRQOFFDQ-UHFFFAOYSA-N 0.000 claims 1
- YIGUUMSVCOYTDS-UHFFFAOYSA-N n-(3-chlorophenyl)-5-[2-(cyclohexen-1-yl)ethylsulfamoyl]-2-fluorobenzamide Chemical compound FC1=CC=C(S(=O)(=O)NCCC=2CCCCC=2)C=C1C(=O)NC1=CC=CC(Cl)=C1 YIGUUMSVCOYTDS-UHFFFAOYSA-N 0.000 claims 1
- HGYFGBSBOAUQHG-UHFFFAOYSA-N n-(4-chlorophenyl)-3-(diethylsulfamoyl)benzamide Chemical compound CCN(CC)S(=O)(=O)C1=CC=CC(C(=O)NC=2C=CC(Cl)=CC=2)=C1 HGYFGBSBOAUQHG-UHFFFAOYSA-N 0.000 claims 1
- MCWYIVFETHLTHK-UHFFFAOYSA-N n-(4-chlorophenyl)-3-[(2-chlorophenyl)methylsulfamoyl]-4-fluorobenzamide Chemical compound FC1=CC=C(C(=O)NC=2C=CC(Cl)=CC=2)C=C1S(=O)(=O)NCC1=CC=CC=C1Cl MCWYIVFETHLTHK-UHFFFAOYSA-N 0.000 claims 1
- YAFODRLJFSCWHU-UHFFFAOYSA-N n-(4-chlorophenyl)-3-[(2-methylphenyl)sulfamoyl]benzamide Chemical compound CC1=CC=CC=C1NS(=O)(=O)C1=CC=CC(C(=O)NC=2C=CC(Cl)=CC=2)=C1 YAFODRLJFSCWHU-UHFFFAOYSA-N 0.000 claims 1
- QMHDIYFUNSUQKI-UHFFFAOYSA-N n-(4-chlorophenyl)-3-[(3-fluorophenyl)sulfamoyl]benzamide Chemical compound FC1=CC=CC(NS(=O)(=O)C=2C=C(C=CC=2)C(=O)NC=2C=CC(Cl)=CC=2)=C1 QMHDIYFUNSUQKI-UHFFFAOYSA-N 0.000 claims 1
- CKYXLFLJAUDXPD-UHFFFAOYSA-N n-(4-chlorophenyl)-5-[2-(3,4-dimethoxyphenyl)ethylsulfamoyl]-2-fluorobenzamide Chemical compound C1=C(OC)C(OC)=CC=C1CCNS(=O)(=O)C1=CC=C(F)C(C(=O)NC=2C=CC(Cl)=CC=2)=C1 CKYXLFLJAUDXPD-UHFFFAOYSA-N 0.000 claims 1
- ZMBJURWSFGFJRY-UHFFFAOYSA-N n-[2-chloro-5-(trifluoromethyl)phenyl]-4-fluoro-3-sulfamoylbenzamide Chemical compound C1=C(F)C(S(=O)(=O)N)=CC(C(=O)NC=2C(=CC=C(C=2)C(F)(F)F)Cl)=C1 ZMBJURWSFGFJRY-UHFFFAOYSA-N 0.000 claims 1
- QPISBSFLDIZASE-UHFFFAOYSA-N n-benzyl-3-(benzylsulfamoyl)-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NCC=2C=CC=CC=2)C=C1S(=O)(=O)NCC1=CC=CC=C1 QPISBSFLDIZASE-UHFFFAOYSA-N 0.000 claims 1
- MQCJWNAWLZTGQX-UHFFFAOYSA-N n-benzyl-4-bromo-3-(diethylsulfamoyl)benzamide Chemical compound C1=C(Br)C(S(=O)(=O)N(CC)CC)=CC(C(=O)NCC=2C=CC=CC=2)=C1 MQCJWNAWLZTGQX-UHFFFAOYSA-N 0.000 claims 1
- DCADFUUGMOJXGT-UHFFFAOYSA-N n-benzyl-4-chloro-3-piperidin-1-ylsulfonylbenzamide Chemical compound ClC1=CC=C(C(=O)NCC=2C=CC=CC=2)C=C1S(=O)(=O)N1CCCCC1 DCADFUUGMOJXGT-UHFFFAOYSA-N 0.000 claims 1
- DQBFOWJYVZUYLC-UHFFFAOYSA-N n-benzyl-4-methyl-3-(4-methylpiperidin-1-yl)sulfonylbenzamide Chemical compound C1CC(C)CCN1S(=O)(=O)C1=CC(C(=O)NCC=2C=CC=CC=2)=CC=C1C DQBFOWJYVZUYLC-UHFFFAOYSA-N 0.000 claims 1
- RPVXKBFDFCOLQP-UHFFFAOYSA-N n-phenyl-3-(pyridin-3-ylmethylsulfamoyl)benzamide Chemical compound C=1C=CC(S(=O)(=O)NCC=2C=NC=CC=2)=CC=1C(=O)NC1=CC=CC=C1 RPVXKBFDFCOLQP-UHFFFAOYSA-N 0.000 claims 1
- GJXPMGCXUXSFJW-UHFFFAOYSA-N n-phenyl-3-sulfamoylbenzamide Chemical compound NS(=O)(=O)C1=CC=CC(C(=O)NC=2C=CC=CC=2)=C1 GJXPMGCXUXSFJW-UHFFFAOYSA-N 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000010898 silica gel chromatography Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- AXNUZKSSQHTNPZ-UHFFFAOYSA-N 3,4-difluoroaniline Chemical compound NC1=CC=C(F)C(F)=C1 AXNUZKSSQHTNPZ-UHFFFAOYSA-N 0.000 description 3
- CISMZCVQNVNWJW-UHFFFAOYSA-N 5-chlorosulfonyl-2-fluorobenzoic acid Chemical compound OC(=O)C1=CC(S(Cl)(=O)=O)=CC=C1F CISMZCVQNVNWJW-UHFFFAOYSA-N 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000003810 ethyl acetate extraction Methods 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- LJMXGSOXXVIIBX-UHFFFAOYSA-N 5-(butan-2-ylsulfamoyl)-2-fluorobenzoic acid Chemical compound CCC(C)NS(=O)(=O)C1=CC=C(F)C(C(O)=O)=C1 LJMXGSOXXVIIBX-UHFFFAOYSA-N 0.000 description 1
- TVMQMTHQSPBXJO-UHFFFAOYSA-N 5-(cyclohexylsulfamoyl)-2-fluorobenzoic acid Chemical compound C1=C(F)C(C(=O)O)=CC(S(=O)(=O)NC2CCCCC2)=C1 TVMQMTHQSPBXJO-UHFFFAOYSA-N 0.000 description 1
- FWZLBJWLCHVGSO-UHFFFAOYSA-N 5-(cyclopentylsulfamoyl)-2-fluorobenzoic acid Chemical compound C1=C(F)C(C(=O)O)=CC(S(=O)(=O)NC2CCCC2)=C1 FWZLBJWLCHVGSO-UHFFFAOYSA-N 0.000 description 1
- JPYQFYIEOUVJDU-UHFFFAOYSA-N beclamide Chemical compound ClCCC(=O)NCC1=CC=CC=C1 JPYQFYIEOUVJDU-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000000234 capsid Anatomy 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
- 210000000981 epithelium Anatomy 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- -1 patches Substances 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161503830P | 2011-07-01 | 2011-07-01 | |
| US61/503,830 | 2011-07-01 | ||
| PCT/US2012/044775 WO2013006394A1 (en) | 2011-07-01 | 2012-06-29 | Sulfamoylbenzamide derivatives as antiviral agents against hbv infection |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016143481A Division JP6516705B2 (ja) | 2011-07-01 | 2016-07-21 | Ｈｂｖ感染に対する抗ウイルス剤としてのスルファモイルベンズアミド誘導体 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014523901A JP2014523901A (ja) | 2014-09-18 |
| JP2014523901A5 true JP2014523901A5 (enExample) | 2015-08-20 |
| JP5977347B2 JP5977347B2 (ja) | 2016-08-24 |
Family
ID=47437368
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014519057A Expired - Fee Related JP5977347B2 (ja) | 2011-07-01 | 2012-06-29 | Ｈｂｖ感染に対する抗ウイルス剤としてのスルファモイルベンズアミド誘導体 |
| JP2016143481A Expired - Fee Related JP6516705B2 (ja) | 2011-07-01 | 2016-07-21 | Ｈｂｖ感染に対する抗ウイルス剤としてのスルファモイルベンズアミド誘導体 |
| JP2019077562A Pending JP2019151639A (ja) | 2011-07-01 | 2019-04-16 | Ｈｂｖ感染に対する抗ウイルス剤としてのスルファモイルベンズアミド誘導体 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016143481A Expired - Fee Related JP6516705B2 (ja) | 2011-07-01 | 2016-07-21 | Ｈｂｖ感染に対する抗ウイルス剤としてのスルファモイルベンズアミド誘導体 |
| JP2019077562A Pending JP2019151639A (ja) | 2011-07-01 | 2019-04-16 | Ｈｂｖ感染に対する抗ウイルス剤としてのスルファモイルベンズアミド誘導体 |
Country Status (5)
| Country | Link |
|---|---|
| US (5) | US9399619B2 (enExample) |
| EP (2) | EP2726459B1 (enExample) |
| JP (3) | JP5977347B2 (enExample) |
| CN (2) | CN106166157B (enExample) |
| WO (1) | WO2013006394A1 (enExample) |
Families Citing this family (125)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2726459B1 (en) | 2011-07-01 | 2019-09-11 | Baruch S. Blumberg Institute | Sulfamoylbenzamide derivatives as antiviral agents against hbv infection |
| JP5977837B2 (ja) | 2011-12-21 | 2016-08-24 | ノヴィラ・セラピューティクス・インコーポレイテッド | Ｂ型肝炎抗ウイルス剤 |
| CN104902885A (zh) | 2012-08-28 | 2015-09-09 | 爱尔兰詹森科学公司 | 氨磺酰基-芳基酰胺和其作为药物用于治疗乙型肝炎的用途 |
| PT2890683T (pt) | 2012-08-28 | 2017-01-17 | Janssen Sciences Ireland Uc | Derivados de sulfamoílo bicíclicos fundidos e a sua utilização como medicamentos para o tratamento da hepatite b |
| WO2014106019A2 (en) * | 2012-12-27 | 2014-07-03 | Philadelphia Health & Education Corporation, D/B/A Drexel | Novel antiviral agents against hbv infection |
| BR112015020242A2 (pt) * | 2013-02-28 | 2017-07-18 | Janssen Sciences Ireland Uc | sulfamoil-arilamidas e seu uso como medicamentos para o tratamento da hepatite b |
| WO2014165128A2 (en) | 2013-03-12 | 2014-10-09 | Novira Therapeutics, Inc. | Hepatitis b antiviral agents |
| JP6419155B2 (ja) * | 2013-04-03 | 2018-11-07 | ヤンセン・サイエンシズ・アイルランド・ユーシー | Ｎ−フェニル−カルボキサミド誘導体およびｂ型肝炎を治療するための医薬品としてのその使用 |
| MX366787B (es) * | 2013-05-17 | 2019-07-23 | Janssen Sciences Ireland Uc | Derivados de sulfamoiltiofenamida y su uso como medicamentos para tratar la hepatitis b. |
| JO3603B1 (ar) | 2013-05-17 | 2020-07-05 | Janssen Sciences Ireland Uc | مشتقات سلفامويل بيرولاميد واستخدامها كادوية لمعالجة التهاب الكبد نوع بي |
| DK3024819T3 (en) | 2013-07-25 | 2018-06-06 | Janssen Sciences Ireland Uc | GLYOXAMIDE-SUBSTITUTED PYRROLAMIDE DERIVATIVES AND THE USE THEREOF AS MEDICINES FOR TREATING HEPATITIS B |
| EA034448B1 (ru) * | 2013-10-23 | 2020-02-10 | Янссен Сайенсиз Айрлэнд Юси | Производные карбоксамида и их применение в качестве медикаментов для лечения гепатита b |
| CA2928003A1 (en) | 2013-11-14 | 2015-05-21 | Novira Therapeutics, Inc. | Azepane derivatives and methods of treating hepatitis b infections |
| US9181288B2 (en) | 2014-01-16 | 2015-11-10 | Novira Therapeutics, Inc. | Azepane derivatives and methods of treating hepatitis B infections |
| US10392349B2 (en) | 2014-01-16 | 2019-08-27 | Novira Therapeutics, Inc. | Azepane derivatives and methods of treating hepatitis B infections |
| US9169212B2 (en) * | 2014-01-16 | 2015-10-27 | Novira Therapeutics, Inc. | Azepane derivatives and methods of treating hepatitis B infections |
| CN106232136A (zh) | 2014-02-05 | 2016-12-14 | 诺维拉治疗公司 | 用于治疗hbv感染的联合疗法 |
| CA2932551A1 (en) * | 2014-02-06 | 2015-08-13 | Janssen Sciences Ireland Uc | Sulphamoylpyrrolamide derivatives and the use thereof as medicaments for the treatment of hepatitis b |
| PL3116316T3 (pl) * | 2014-03-13 | 2020-03-31 | Indiana University Research And Technology Corporation | Allosteryczne modulatory białka rdzeniowego wirusa zapalenia wątroby typu B |
| US9400280B2 (en) | 2014-03-27 | 2016-07-26 | Novira Therapeutics, Inc. | Piperidine derivatives and methods of treating hepatitis B infections |
| US20170266197A1 (en) * | 2014-05-09 | 2017-09-21 | Indiana University Research And Technology Corporation | Methods and compositions for treating hepatitis b virus infections |
| ES2874579T3 (es) | 2014-06-11 | 2021-11-05 | Venatorx Pharmaceuticals Inc | Inhibidores de betalactamasa |
| US9765050B2 (en) * | 2014-12-30 | 2017-09-19 | Novira Therapeutics, Inc. | Pyridyl reverse sulfonamides for HBV treatment |
| CA2980298A1 (en) | 2015-03-19 | 2016-09-22 | Novira Therapeutics, Inc. | Azocane and azonane derivatives and methods of treating hepatitis b infections |
| US10442788B2 (en) | 2015-04-01 | 2019-10-15 | Enanta Pharmaceuticals, Inc. | Hepatitis B antiviral agents |
| CN107922377A (zh) * | 2015-04-17 | 2018-04-17 | 美国印第安纳大学研究和技术公司 | 乙肝病毒组装效应子 |
| WO2016183266A1 (en) | 2015-05-13 | 2016-11-17 | Enanta Pharmaceuticals, Inc. | Ehpatitis b antiviral agents |
| US10875876B2 (en) | 2015-07-02 | 2020-12-29 | Janssen Sciences Ireland Uc | Cyclized sulfamoylarylamide derivatives and the use thereof as medicaments for the treatment of hepatitis B |
| US10179131B2 (en) | 2015-07-13 | 2019-01-15 | Enanta Pharmaceuticals, Inc. | Hepatitis B antiviral agents |
| US10301255B2 (en) | 2015-07-22 | 2019-05-28 | Enanta Pharmaceuticals, Inc. | Hepatitis B antiviral agents |
| TWI721016B (zh) * | 2015-09-15 | 2021-03-11 | 美商艾森伯利生物科學公司 | B型肝炎核心蛋白質調節劑 |
| CN108430971A (zh) | 2015-09-29 | 2018-08-21 | 诺维拉治疗公司 | 乙型肝炎抗病毒剂的晶体形式 |
| WO2017136403A1 (en) | 2016-02-02 | 2017-08-10 | Enanta Pharmaceuticals, Inc. | Hepatitis b antiviral agents |
| KR101857714B1 (ko) * | 2016-02-05 | 2018-05-15 | 연세대학교 산학협력단 | 신규 아미드 화합물 및 이의 용도 |
| EP3426245B1 (en) * | 2016-03-07 | 2022-12-14 | Enanta Pharmaceuticals, Inc. | Hepatitis b antiviral agents |
| KR102390675B1 (ko) * | 2016-03-09 | 2022-04-26 | 에모리 유니버시티 | 항바이러스제에 의한 b형 간염 바이러스의 제거 |
| CN109640980A (zh) | 2016-04-15 | 2019-04-16 | 诺维拉治疗公司 | 包含壳体装配抑制剂的组合和方法 |
| WO2017214395A1 (en) | 2016-06-10 | 2017-12-14 | Enanta Pharmaceuticals, Inc. | Hepatitis b antiviral agents |
| WO2018039131A1 (en) | 2016-08-22 | 2018-03-01 | Protiva Biotherapeutics, Inc. | Anti-pd-1 antibodies, or fragments thereof, for treating hepatitis b |
| JOP20190024A1 (ar) | 2016-08-26 | 2019-02-19 | Gilead Sciences Inc | مركبات بيروليزين بها استبدال واستخداماتها |
| CA3037151A1 (en) | 2016-09-15 | 2018-03-22 | Assembly Biosciences, Inc. | Hepatitis b core protein modulators |
| US10821103B2 (en) | 2016-11-07 | 2020-11-03 | Arbutus Biopharma Corporation | Substituted pyridinone-containing trycyclic compounds, and methods using same |
| WO2018086530A1 (zh) * | 2016-11-08 | 2018-05-17 | 正大天晴药业集团股份有限公司 | 作为cccDNA抑制剂的磺酰胺类化合物 |
| AU2018217664B2 (en) * | 2017-02-07 | 2022-03-03 | Janssen Pharmaceutica Nv | Sulphamoylaryl derivatives and use thereof as medicaments for the treatment of liver fibrosis |
| RU2650610C1 (ru) | 2017-02-28 | 2018-04-16 | Васильевич Иващенко Александр | Противовирусная композиция и способ ее применения |
| AU2018227811A1 (en) | 2017-03-02 | 2019-09-19 | Assembly Biosciences, Inc. | Cyclic sulfamide compounds and methods of using same |
| US11040965B2 (en) | 2017-03-13 | 2021-06-22 | Assembly Biosciences, Inc. | Process for making Hepatitis B core protein modulators |
| CA3056886A1 (en) | 2017-03-21 | 2018-09-27 | Arbutus Biopharma Corporation | Substituted dihydroindene-4-carboxamides and analogs thereof, and methods using same |
| US11130740B2 (en) | 2017-04-25 | 2021-09-28 | Arbutus Biopharma Corporation | Substituted 2,3-dihydro-1H-indene analogs and methods using same |
| JP7123429B2 (ja) | 2017-05-04 | 2022-08-23 | シャンハイ ロングウッド バイオファルマシューティカルズ カンパニー リミテッド | 二環式縮合環系ヌクレオカプシド阻害剤および薬物としてｂ型肝炎を治療するためのその使用 |
| JP2020525490A (ja) | 2017-06-27 | 2020-08-27 | ヤンセン ファーマシューティカ エヌ．ベー． | ヘテロアリールジヒドロピリミジン誘導体及びｂ型肝炎感染を治療する方法 |
| CN109251212A (zh) * | 2017-07-14 | 2019-01-22 | 上海长森药业有限公司 | 内环硫醚酰胺-芳基酰胺类化合物及其治疗乙型肝炎的用途 |
| CN109251158B (zh) * | 2017-07-14 | 2023-05-23 | 上海长森药业有限公司 | 硫脒酰胺类化合物及其用于乙型肝炎治疗的用途 |
| AU2018326474B2 (en) | 2017-08-28 | 2024-07-25 | Enanta Pharmaceuticals, Inc. | Hepatitis B antiviral agents |
| TW201912153A (zh) * | 2017-08-30 | 2019-04-01 | 加拿大商愛彼特生物製藥公司 | 用於治療ｂ型肝炎的化合物、醫藥組合物及方法 |
| MA50524A (fr) | 2017-11-02 | 2020-09-09 | Aicuris Gmbh & Co Kg | Nouveaux indole-2-carboxamides à substitution amino-thiazole hautement actifs agissant contre le virus de l'hépatite b (vhb) |
| EA202091114A1 (ru) | 2017-11-02 | 2020-07-24 | Айкурис Гмбх Унд Ко. Кг | Новые высокоактивные пиразолопиперидин-замещенные индол-2-карбоксамиды, активные против вируса гепатита в (hbv) |
| WO2019096241A1 (zh) * | 2017-11-16 | 2019-05-23 | 正大天晴药业集团股份有限公司 | 抗HBV的四氢异噁唑并[4,3-c]吡啶类化合物 |
| CN111315749A (zh) * | 2017-11-17 | 2020-06-19 | 诺华股份有限公司 | 新颖的二氢异噁唑化合物及其在治疗乙型肝炎中的用途 |
| TW201927789A (zh) | 2017-12-06 | 2019-07-16 | 美商因那塔製藥公司 | B型肝炎抗病毒試劑 |
| WO2019113175A1 (en) | 2017-12-06 | 2019-06-13 | Enanta Pharmaceuticals, Inc. | Hepatitis b antiviral agents |
| US11247965B2 (en) | 2017-12-11 | 2022-02-15 | VenatoRx Pharmaceuticals, Inc. | Hepatitis B capsid assembly modulators |
| WO2019143902A2 (en) | 2018-01-22 | 2019-07-25 | Enanta Pharmaceuticals, Inc. | Substituted heterocycles as antiviral agents |
| US10836769B2 (en) | 2018-02-26 | 2020-11-17 | Gilead Sciences, Inc. | Substituted pyrrolizine compounds and uses thereof |
| JP2021514982A (ja) | 2018-02-28 | 2021-06-17 | ノバルティス アーゲー | インドール−２−カルボニル化合物及びｂ型肝炎治療のためのそれらの使用 |
| EA202092171A1 (ru) | 2018-03-14 | 2020-12-01 | Янссен Сайенсиз Айрлэнд Анлимитед Компани | Схема дозирования модулятора сборки капсида |
| US10729688B2 (en) | 2018-03-29 | 2020-08-04 | Enanta Pharmaceuticals, Inc. | Hepatitis B antiviral agents |
| WO2019191624A1 (en) | 2018-03-29 | 2019-10-03 | Arbutus Biopharma, Inc. | Substituted 1,1'-biphenyl compounds, analogues thereof, and methods using same |
| WO2019206072A1 (zh) * | 2018-04-24 | 2019-10-31 | 浙江海正药业股份有限公司 | 磺酰胺芳基甲酰胺衍生物及其制备方法和用途 |
| US10590076B2 (en) | 2018-06-11 | 2020-03-17 | VenatoRx Pharmaceuticals, Inc. | Hepatitis B capsid assembly modulators |
| EP3597637A1 (en) | 2018-07-19 | 2020-01-22 | Irbm S.P.A. | Inhibitors of hepatitis b virus |
| EP3597653A1 (en) | 2018-07-19 | 2020-01-22 | Irbm S.P.A. | Cyclic inhibitors of hepatitis b virus |
| CN108997176B (zh) * | 2018-07-27 | 2021-07-02 | 温州医科大学 | 一种4-氯-n-取代苯基-3-磺酰氨基苯甲酰胺类化合物及其制备和抗肿瘤应用 |
| TWI869058B (zh) | 2018-07-27 | 2025-01-01 | 加拿大商愛彼特生物製藥公司 | 經取代四氫環戊[c]吡咯、經取代二氫吡咯，其類似物及使用其之方法 |
| CN108863860B (zh) * | 2018-07-27 | 2021-08-06 | 温州医科大学 | 一种n-取代苯基-3-磺酰氨基苯甲酰胺类化合物及其制备和抗乳腺癌活性的应用 |
| US11053235B2 (en) | 2018-08-09 | 2021-07-06 | Janssen Sciences Ireland Unlimited Company | Substituted 1,4-dihydropyrimidines for the treatment of HBV infection or HBV-induced diseases |
| EP3608326A1 (en) | 2018-08-10 | 2020-02-12 | Irbm S.P.A. | Tricyclic inhibitors of hepatitis b virus |
| AR116474A1 (es) | 2018-09-21 | 2021-05-12 | Enanta Pharm Inc | DERIVADOS DEL ÁCIDO 6,7-DIHIDRO-2H-BENZOFURO[2,3-a]QUINOLIZIN-3-CARBOXÍLICO COMO AGENTES ANTIVIRALES PARA EL TRATAMIENTO O PREVENCIÓN DE UNA INFECCIÓN POR HBV |
| JP7648528B2 (ja) * | 2018-10-05 | 2025-03-18 | エモリー ユニバーシティ | モノマーおよびマルチマー抗ｈｂｖ薬 |
| BR112021007602A2 (pt) | 2018-10-22 | 2021-07-27 | Assembly Biosciences, Inc. | compostos de heteroaril carboxamida de 5 membros para tratamento de hbv |
| WO2020087107A1 (en) | 2018-10-31 | 2020-05-07 | The University Of Sydney | Compositions and methods for treating viral infections |
| UY38436A (es) | 2018-11-02 | 2020-05-29 | Aicuris Gmbh & Co Kg | Nuevas 6,7-dihidro-4h-pirazolo[1,5-a] pirazinindol-2-carboxamidas activas contra el virus de la hepatitis b (vhb) |
| UY38439A (es) | 2018-11-02 | 2020-05-29 | Aicuris Gmbh & Co Kg | Novedosas urea 6,7-dihidro-4h-pirazolo[4,3-c]piridinas activas contra el virus de la hepatitis b (vhb) |
| UY38434A (es) | 2018-11-02 | 2020-05-29 | Aicuris Gmbh & Co Kg | Nuevas 6,7-dihidro-4h-pirazolo[1,5-a]pirazin indol-2-carboxamidas activas contra el virus de la hepatitis b (hbv) |
| AR117188A1 (es) | 2018-11-02 | 2021-07-21 | Aicuris Gmbh & Co Kg | Derivados de urea 6,7-dihidro-4h-pirazolo[1,5-a]pirazinas activas contra el virus de la hepatitis b (vhb) |
| CN113039187A (zh) | 2018-11-02 | 2021-06-25 | 艾库里斯有限及两合公司 | 抗乙型肝炎病毒HBV的脲6,7-二氢-4H-噻唑并[5,4-c]吡啶活性剂 |
| AR116948A1 (es) | 2018-11-02 | 2021-06-30 | Aicuris Gmbh & Co Kg | Derivados de urea 6,7-dihidro-4h-pirazolo[1,5-a]pirazinas activas contra el virus de la hepatitis b (vhb) |
| BR112021009854A2 (pt) | 2018-11-21 | 2021-08-17 | Enanta Pharmaceuticals, Inc. | heterociclos funcionalizados como agentes antivirais |
| TWI827760B (zh) | 2018-12-12 | 2024-01-01 | 加拿大商愛彼特生物製藥公司 | 經取代之芳基甲基脲類及雜芳基甲基脲類、其類似物及其使用方法 |
| CN111434665B (zh) * | 2019-01-11 | 2023-03-10 | 上海长森药业有限公司 | 内环硫脒酰胺-芳基酰胺类化合物及其治疗乙型肝炎的用途 |
| MX2021010145A (es) | 2019-02-22 | 2021-09-14 | Janssen Sciences Ireland Unlimited Co | Derivados de amida utiles en el tratamiento de una infeccion por vhb o de enfermedades inducidas por vhb. |
| KR20220003023A (ko) | 2019-04-30 | 2022-01-07 | 아이쿠리스 게엠베하 운트 코. 카게 | B형 간염 바이러스 (hbv)에 대해 활성인 신규 옥살릴 피페라진 |
| CA3138384A1 (en) | 2019-04-30 | 2020-11-05 | Aicuris Gmbh & Co. Kg | Novel phenyl and pyridyl ureas active against the hepatitis b virus (hbv) |
| JP2022533007A (ja) | 2019-04-30 | 2022-07-21 | アイクリス ゲゼルシャフト ミット ベシュレンクテル ハフツング ウント コンパニー コマンディトゲゼルシャフト | Ｂ型肝炎ウイルス（ｈｂｖ）に対し活性な新規のインドリジン－２－カルボキサミド |
| CU20210088A7 (es) | 2019-04-30 | 2022-06-06 | Aicuris Gmbh & Co Kg | Compuestos derivados sustituidos de indol-2-carboxamidas activas contra el virus de la hepatitis b (vhb) |
| BR112021021454A2 (pt) | 2019-05-06 | 2021-12-21 | Janssen Sciences Ireland Unlimited Co | Derivados de amida úteis no tratamento da infecção por hbv ou doenças induzidas por hbv |
| UY38705A (es) | 2019-05-23 | 2020-12-31 | Irbm S P A | Inhibidores tricíclicos sustituidos con oxalamido del virus de hepatitis b |
| EP3825318A1 (en) | 2019-11-25 | 2021-05-26 | Promidis S.r.l. | Oxalamido-substituted tricyclic inhibitors of hepatitis b virus |
| EP3741762A1 (en) | 2019-05-23 | 2020-11-25 | Irbm S.P.A. | Oxalamido-substituted tricyclic inhibitors of hepatitis b virus |
| AU2020282318A1 (en) | 2019-05-24 | 2021-12-02 | Assembly Biosciences, Inc. | Pharmaceutical compositions for the treatment of HBV |
| WO2020247444A1 (en) | 2019-06-03 | 2020-12-10 | Enanta Pharmaceuticals, Inc, | Hepatitis b antiviral agents |
| WO2020247575A1 (en) * | 2019-06-04 | 2020-12-10 | Enanta Pharmaceuticals, Inc. | Hepatitis b antiviral agents |
| WO2020247561A1 (en) | 2019-06-04 | 2020-12-10 | Enanta Pharmaceuticals, Inc, | Hepatitis b antiviral agents |
| US11738019B2 (en) | 2019-07-11 | 2023-08-29 | Enanta Pharmaceuticals, Inc. | Substituted heterocycles as antiviral agents |
| WO2021055425A2 (en) | 2019-09-17 | 2021-03-25 | Enanta Pharmaceuticals, Inc. | Functionalized heterocycles as antiviral agents |
| CA3165101A1 (en) | 2019-12-20 | 2021-06-24 | Arbutus Biopharma Corporation | Synthetic processes and intermediates |
| US11802125B2 (en) | 2020-03-16 | 2023-10-31 | Enanta Pharmaceuticals, Inc. | Functionalized heterocyclic compounds as antiviral agents |
| CN111393391B (zh) * | 2020-04-16 | 2022-07-26 | 南京安纳康生物科技有限公司 | 用于乙型肝炎病毒感染的抗病毒剂 |
| CN111349056B (zh) * | 2020-04-16 | 2022-08-02 | 南京安纳康生物科技有限公司 | 用于乙型肝炎病毒感染的抗病毒剂 |
| WO2021216660A1 (en) | 2020-04-22 | 2021-10-28 | Assembly Biosciences, Inc. | 5-membered heteroaryl carboxamide compounds for treatment of hbv |
| WO2021216661A1 (en) | 2020-04-22 | 2021-10-28 | Assembly Biosciences, Inc. | Pyrazole carboxamide compounds for treatment of hbv |
| WO2021216642A1 (en) | 2020-04-22 | 2021-10-28 | Assembly Biosciences, Inc. | Pyrazole carboxamide compounds for treatment of hbv |
| WO2021216656A1 (en) | 2020-04-22 | 2021-10-28 | Assembly Biosciences, Inc. | 5-membered heteroaryl carboxamide compounds for treatment of hbv |
| WO2023069544A1 (en) | 2021-10-20 | 2023-04-27 | Assembly Biosciences, Inc. | 5-membered heteroaryl carboxamide compounds for treatment of hbv |
| WO2023069547A1 (en) | 2021-10-20 | 2023-04-27 | Assembly Biosciences, Inc. | 5-membered heteroaryl carboxamide compounds for treatment of hbv |
| WO2023069545A1 (en) | 2021-10-20 | 2023-04-27 | Assembly Biosciences, Inc. | 5-membered heteroaryl carboxamide compounds for treatment of hbv |
| WO2023164179A1 (en) | 2022-02-25 | 2023-08-31 | Assembly Biosciences, Inc. | Benzothia(dia)zepine compounds for treatment of hbv and hdv |
| US20250163009A1 (en) | 2022-02-25 | 2025-05-22 | Assembly Biosciences, Inc. | Benzothia(dia)zepine compounds for treatment of hbv and hdv |
| WO2023164186A1 (en) | 2022-02-25 | 2023-08-31 | Assembly Biosciences, Inc. | Benzothia(dia)zepine compounds for treatment of hbv and hdv |
| WO2023164181A1 (en) | 2022-02-25 | 2023-08-31 | Assembly Biosciences, Inc. | Benzothia(dia)zepine compounds for treatment of hbv and hdv |
| WO2023175185A1 (en) | 2022-03-17 | 2023-09-21 | Forx Therapeutics Ag | 2,4-dioxo-1,4-dihydroquinazoline derivatives as parg inhibitors for the treatment of cancer |
| WO2023175184A1 (en) | 2022-03-17 | 2023-09-21 | Forx Therapeutics Ag | 2,4-dioxo-1,4-dihydroquinazoline derivatives as parg inhibitors for the treatment of cancer |
| CN115677545B (zh) * | 2022-10-28 | 2024-03-15 | 潍坊医学院 | 一种抗hbv磺胺苯甲酰胺类衍生物及其制备方法和应用 |
| WO2025043094A1 (en) | 2023-08-23 | 2025-02-27 | Assembly Biosciences, Inc. | Benzothia(dia)zepine compounds for treatment of hbv and hdv |
| WO2025046148A1 (en) | 2023-09-01 | 2025-03-06 | Forx Therapeutics Ag | Novel parg inhibitors |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US422547A (en) * | 1890-03-04 | Knife | ||
| US3055905A (en) | 1958-03-04 | 1962-09-25 | Geigy Chem Corp | New sulphamyl benzamides |
| GB912060A (en) | 1960-05-09 | 1962-12-05 | British Drug Houses Ltd | 4-chloro-3-sulphamylbenzanilides |
| GB921520A (en) | 1960-10-10 | 1963-03-20 | British Drug Houses Ltd | 4-fluoro and 4-bromo-3-sulphamylbenzanilides |
| US3602786A (en) * | 1970-06-22 | 1971-08-31 | Georgy Ignatievich Izhelya | Induction linear electric motor |
| US4115155A (en) * | 1974-05-03 | 1978-09-19 | Bethlehem Steel Corporation | Low carbon high yield and tensile strength steel and method of manufacture |
| GB9109557D0 (en) * | 1991-05-02 | 1991-06-26 | Wellcome Found | Chemical compounds |
| JPH0959236A (ja) | 1995-08-23 | 1997-03-04 | Dai Ichi Seiyaku Co Ltd | ベンズアミド化合物 |
| US5939423A (en) * | 1997-04-16 | 1999-08-17 | Sciclone Pharmaceuticals, Inc. | Treatment of hepatitis B infection with thymosin alpha 1 and famciclovir |
| GB9800750D0 (en) * | 1998-01-14 | 1998-03-11 | Lilly Co Eli | Pharmaceutical compound |
| WO2006044645A2 (en) * | 2004-10-13 | 2006-04-27 | Adolor Corporation | Sulfamoyl benzamides and methods of their use |
| US20080021063A1 (en) * | 2006-07-18 | 2008-01-24 | Kazantsev Aleksey G | Compositions and methods for modulating sirtuin activity |
| US8153803B2 (en) | 2006-07-18 | 2012-04-10 | The General Hospital Corporation | Compositions and methods for modulating sirtuin activity |
| WO2008022171A1 (en) * | 2006-08-17 | 2008-02-21 | Boehringer Ingelheim International Gmbh | Methods of using aryl sulfonyl compounds effective as soluble epoxide hydrolase inhibitors |
| CA2687964A1 (en) * | 2007-06-01 | 2009-02-19 | The Trustees Of Princeton University | Treatment of viral infections by modulation of host cell metabolic pathways |
| WO2009018219A2 (en) * | 2007-07-28 | 2009-02-05 | University Of Chicago | Methods and compositions for modulating rad51 and homologous recombination |
| CA2695071A1 (en) * | 2007-08-02 | 2009-02-05 | F. Hoffmann-La Roche Ag | The use of benzamide derivatives for the treatment of cns disorders |
| EP2219646A4 (en) * | 2007-12-21 | 2010-12-22 | Univ Rochester | PROCESS FOR EXTENDING THE LIFE OF EUKARYOTIC ORGANISMS |
| US20100009970A1 (en) * | 2008-03-19 | 2010-01-14 | Combinatorx (Singapore) Pte. Ltd. | Compositions and methods for treatment of viral diseases |
| ES2527589T3 (es) * | 2008-04-24 | 2015-01-27 | Msd K.K. | Inhibidor de la enzima de elongación de ácidos grasos de cadena larga que comprende un derivado de arilsulfonilo como principio activo |
| FR2933698A1 (fr) * | 2008-07-09 | 2010-01-15 | Servier Lab | Nouveaux derives de benzothiadiazines cycloalkylees, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| WO2010123139A1 (ja) * | 2009-04-24 | 2010-10-28 | 持田製薬株式会社 | スルファモイル基を有するアリールカルボキサミド誘導体 |
| EP2726459B1 (en) | 2011-07-01 | 2019-09-11 | Baruch S. Blumberg Institute | Sulfamoylbenzamide derivatives as antiviral agents against hbv infection |
| JP5977837B2 (ja) * | 2011-12-21 | 2016-08-24 | ノヴィラ・セラピューティクス・インコーポレイテッド | Ｂ型肝炎抗ウイルス剤 |
| BR112014021498A2 (pt) * | 2012-02-29 | 2017-07-18 | Institute For Hepatitis And Virus Res | composto, composição e método para tratar uma doença associada com formação de dna circular covalentemente fechado |
-
2012
- 2012-06-29 EP EP12807810.2A patent/EP2726459B1/en active Active
- 2012-06-29 CN CN201610312350.0A patent/CN106166157B/zh not_active Expired - Fee Related
- 2012-06-29 CN CN201280039363.5A patent/CN103889953B/zh not_active Expired - Fee Related
- 2012-06-29 JP JP2014519057A patent/JP5977347B2/ja not_active Expired - Fee Related
- 2012-06-29 WO PCT/US2012/044775 patent/WO2013006394A1/en not_active Ceased
- 2012-06-29 US US14/130,140 patent/US9399619B2/en active Active
- 2012-06-29 EP EP16174324.0A patent/EP3085368A1/en not_active Withdrawn
-
2015
- 2015-12-18 US US14/975,239 patent/US9758477B2/en active Active
-
2016
- 2016-07-21 JP JP2016143481A patent/JP6516705B2/ja not_active Expired - Fee Related
-
2017
- 2017-07-21 US US15/656,769 patent/US20170320818A1/en not_active Abandoned
-
2019
- 2019-04-16 JP JP2019077562A patent/JP2019151639A/ja active Pending
- 2019-07-02 US US16/459,665 patent/US20190337891A1/en not_active Abandoned
-
2020
- 2020-11-23 US US17/101,852 patent/US20210070703A1/en not_active Abandoned
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2014523901A5 (enExample) | ||
| US10995064B2 (en) | Sulfamoyl-arylamides and the use thereof as medicaments for the treatment of hepatitis B | |
| JP6409001B2 (ja) | Ｈｂｖ感染に対する新規抗ウイルス剤 | |
| JP5977347B2 (ja) | Ｈｂｖ感染に対する抗ウイルス剤としてのスルファモイルベンズアミド誘導体 | |
| JP5399237B2 (ja) | ヒトパピローマウイルス阻害剤としてのピペリジン誘導体 | |
| JP6271806B2 (ja) | ウイルス静止化合物としての抗炎症剤 | |
| JP6484168B2 (ja) | 抗ウイルス活性を有するメタンチオン化合物 | |
| US9951058B2 (en) | Compound, pharmaceutically acceptable salt or optical isomer thereof, method for preparing the same, and pharmaceutical composition for prevention or treatment of viral diseases containing same as active ingredient | |
| CA2727911C (fr) | Phenyl-alkyl-piperazines ayant une activite modulatrice du tnf | |
| CN115916345B (zh) | 吡咯并吡啶衍生物及其用途 | |
| CN105263926B (zh) | 苯并噻吩化合物 | |
| JP2011503224A (ja) | 新規なヒトパピローマウイルス阻害剤およびそれを含有する医薬組成物 | |
| HK40059923A (en) | Compound, pharmaceutically acceptable salt or optical isomer thereof, method for preparing same, and pharmaceutical composition for prevention or treatment of viral diseases containing same as active ingredient | |
| HK40059923B (en) | Compound, pharmaceutically acceptable salt or optical isomer thereof, method for preparing same, and pharmaceutical composition for prevention or treatment of viral diseases containing same as active ingredient | |
| CN120923428A (zh) | 流感病毒核酸内切酶抑制剂及其应用 | |
| HK1216253B (en) | Novel compound, pharmaceutically acceptable salt or optical isomer thereof, method for preparing same, and pharmaceutical composition for prevention or treatment of viral diseases containing same as active ingredient | |
| OA17199A (en) | Sulfamoyl-arylamides and the use thereof as medicaments for the treatment of hepatitis B. |