JP2014523901A5 - - Google Patents
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- 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
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- 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
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-
2012
- 2012-06-29 WO PCT/US2012/044775 patent/WO2013006394A1/en not_active Ceased
- 2012-06-29 JP JP2014519057A patent/JP5977347B2/ja not_active Expired - Fee Related
- 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 EP EP16174324.0A patent/EP3085368A1/en not_active Withdrawn
- 2012-06-29 CN CN201280039363.5A patent/CN103889953B/zh not_active Expired - Fee Related
- 2012-06-29 US US14/130,140 patent/US9399619B2/en active Active
-
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
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2020
- 2020-11-23 US US17/101,852 patent/US20210070703A1/en not_active Abandoned
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