JP2013522224A5 - - Google Patents
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- Publication number
- JP2013522224A5 JP2013522224A5 JP2012557233A JP2012557233A JP2013522224A5 JP 2013522224 A5 JP2013522224 A5 JP 2013522224A5 JP 2012557233 A JP2012557233 A JP 2012557233A JP 2012557233 A JP2012557233 A JP 2012557233A JP 2013522224 A5 JP2013522224 A5 JP 2013522224A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- fluoro
- hydrogen
- carboxamide
- phenyl
- 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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- 125000000217 alkyl group Chemical group 0.000 claims 54
- -1 hydroxyalkyloxy Chemical group 0.000 claims 49
- 239000001257 hydrogen Substances 0.000 claims 42
- 229910052739 hydrogen Inorganic materials 0.000 claims 42
- 125000005843 halogen group Chemical group 0.000 claims 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 25
- 150000002431 hydrogen Chemical class 0.000 claims 23
- 125000003545 alkoxy group Chemical group 0.000 claims 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 19
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 19
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 18
- 125000001424 substituent group Chemical group 0.000 claims 17
- 150000001875 compounds Chemical class 0.000 claims 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims 15
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 14
- 125000001188 haloalkyl group Chemical group 0.000 claims 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 9
- 125000004076 pyridyl group Chemical group 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 8
- 125000002393 azetidinyl group Chemical group 0.000 claims 8
- 125000002757 morpholinyl group Chemical group 0.000 claims 8
- 125000004193 piperazinyl group Chemical group 0.000 claims 8
- 125000003386 piperidinyl group Chemical group 0.000 claims 8
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 8
- 125000003282 alkyl amino group Chemical group 0.000 claims 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 7
- 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 claims 7
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 7
- 125000004663 dialkyl amino group Chemical group 0.000 claims 7
- 125000001153 fluoro group Chemical group F* 0.000 claims 7
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims 7
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 7
- 125000005431 alkyl carboxamide group Chemical group 0.000 claims 6
- 125000005602 azabenzimidazolyl group Chemical group 0.000 claims 6
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 4
- 239000005977 Ethylene Substances 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000004103 aminoalkyl group Chemical group 0.000 claims 4
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 4
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 claims 4
- 125000001041 indolyl group Chemical group 0.000 claims 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims 4
- 125000001544 thienyl group Chemical group 0.000 claims 4
- 125000001425 triazolyl group Chemical group 0.000 claims 4
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims 3
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 3
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 3
- 125000005059 halophenyl group Chemical group 0.000 claims 3
- HAPXCTKYPDRDCY-UHFFFAOYSA-N C(C1=CC=CC=C1)N(CC1=CC=CC=C1)C1=C2C(C(=O)NC2=O)=CC=C1 Chemical compound C(C1=CC=CC=C1)N(CC1=CC=CC=C1)C1=C2C(C(=O)NC2=O)=CC=C1 HAPXCTKYPDRDCY-UHFFFAOYSA-N 0.000 claims 2
- 208000005176 Hepatitis C Diseases 0.000 claims 2
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims 2
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 125000005124 aminocycloalkyl group Chemical group 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 2
- 235000010290 biphenyl Nutrition 0.000 claims 2
- 239000004305 biphenyl Substances 0.000 claims 2
- 125000005019 carboxyalkenyl group Chemical group 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 2
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 208000010710 hepatitis C virus infection Diseases 0.000 claims 2
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 2
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 108091032973 (ribonucleotides)n+m Proteins 0.000 claims 1
- UBCHPRBFMUDMNC-UHFFFAOYSA-N 1-(1-adamantyl)ethanamine Chemical compound C1C(C2)CC3CC2CC1(C(N)C)C3 UBCHPRBFMUDMNC-UHFFFAOYSA-N 0.000 claims 1
- BTMVLRBLGJOLCL-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-methyl-5-[2-methyl-5-[[1-(1,5-naphthyridin-2-yl)cyclopropyl]carbamoyl]phenyl]-1-benzofuran-3-carboxamide Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=CC=C1C(C(=CC=1)C)=CC=1C(=O)NC1(C=2N=C3C=CC=NC3=CC=2)CC1 BTMVLRBLGJOLCL-UHFFFAOYSA-N 0.000 claims 1
- FEGDRSNDNOWJMG-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-methyl-5-[2-methyl-5-[[1-(1,6-naphthyridin-2-yl)cyclopropyl]carbamoyl]phenyl]-1-benzofuran-3-carboxamide Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=CC=C1C(C(=CC=1)C)=CC=1C(=O)NC1(C=2N=C3C=CN=CC3=CC=2)CC1 FEGDRSNDNOWJMG-UHFFFAOYSA-N 0.000 claims 1
- MKCPKOUTBSNQHU-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-methyl-5-[2-methyl-5-[[1-(1,7-naphthyridin-2-yl)cyclopropyl]carbamoyl]phenyl]-1-benzofuran-3-carboxamide Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=CC=C1C(C(=CC=1)C)=CC=1C(=O)NC1(C=2N=C3C=NC=CC3=CC=2)CC1 MKCPKOUTBSNQHU-UHFFFAOYSA-N 0.000 claims 1
- XFURMGJPAIPHLW-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-methyl-5-[2-methyl-5-[[1-(1,8-naphthyridin-2-yl)cyclopropyl]carbamoyl]phenyl]-1-benzofuran-3-carboxamide Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=CC=C1C(C(=CC=1)C)=CC=1C(=O)NC1(C=2N=C3N=CC=CC3=CC=2)CC1 XFURMGJPAIPHLW-UHFFFAOYSA-N 0.000 claims 1
- KDLPZIZHSFYXNZ-QGZVFWFLSA-N 4-fluoro-2-(4-fluorophenyl)-5-[4-methoxy-2-methyl-5-[[(1r)-1-([1,3]oxazolo[4,5-c]pyridin-2-yl)ethyl]carbamoyl]phenyl]-n-methyl-1-benzofuran-3-carboxamide Chemical compound O1C2=CC=C(C=3C(=CC(OC)=C(C(=O)N[C@H](C)C=4OC5=CC=NC=C5N=4)C=3)C)C(F)=C2C(C(=O)NC)=C1C1=CC=C(F)C=C1 KDLPZIZHSFYXNZ-QGZVFWFLSA-N 0.000 claims 1
- KDLPZIZHSFYXNZ-KRWDZBQOSA-N 4-fluoro-2-(4-fluorophenyl)-5-[4-methoxy-2-methyl-5-[[(1s)-1-([1,3]oxazolo[4,5-c]pyridin-2-yl)ethyl]carbamoyl]phenyl]-n-methyl-1-benzofuran-3-carboxamide Chemical compound O1C2=CC=C(C=3C(=CC(OC)=C(C(=O)N[C@@H](C)C=4OC5=CC=NC=C5N=4)C=3)C)C(F)=C2C(C(=O)NC)=C1C1=CC=C(F)C=C1 KDLPZIZHSFYXNZ-KRWDZBQOSA-N 0.000 claims 1
- POUBHPCIAURQSZ-UHFFFAOYSA-N 4-fluoro-2-(4-fluorophenyl)-5-[4-methoxy-2-methyl-5-[[1-(1,6-naphthyridin-2-yl)cyclopropyl]carbamoyl]phenyl]-n-methyl-1-benzofuran-3-carboxamide Chemical compound FC1=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=CC=C1C(C(=CC=1OC)C)=CC=1C(=O)NC1(C=2N=C3C=CN=CC3=CC=2)CC1 POUBHPCIAURQSZ-UHFFFAOYSA-N 0.000 claims 1
- NWDHPMSTICZPRW-UHFFFAOYSA-N 4-fluoro-2-(4-fluorophenyl)-5-[4-methoxy-2-methyl-5-[[1-([1,3]oxazolo[4,5-c]pyridin-2-yl)cyclopropyl]carbamoyl]phenyl]-n-methyl-1-benzofuran-3-carboxamide Chemical compound FC1=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=CC=C1C(C(=CC=1OC)C)=CC=1C(=O)NC1(C=2OC3=CC=NC=C3N=2)CC1 NWDHPMSTICZPRW-UHFFFAOYSA-N 0.000 claims 1
- OWOAMPYIKJWQPD-UHFFFAOYSA-N 4-fluoro-2-(4-fluorophenyl)-5-[4-methoxy-2-methyl-5-[[1-([1,3]oxazolo[5,4-c]pyridin-2-yl)cyclopropyl]carbamoyl]phenyl]-n-methyl-1-benzofuran-3-carboxamide Chemical compound FC1=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=CC=C1C(C(=CC=1OC)C)=CC=1C(=O)NC1(C=2OC3=CN=CC=C3N=2)CC1 OWOAMPYIKJWQPD-UHFFFAOYSA-N 0.000 claims 1
- OERSXZVIJIUUCT-UHFFFAOYSA-N 4-fluoro-2-(4-fluorophenyl)-5-[5-[[1-(3h-imidazo[4,5-c]pyridin-2-yl)cyclopropyl]carbamoyl]-2-methylphenyl]-n-methyl-1-benzofuran-3-carboxamide Chemical compound FC1=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=CC=C1C(C(=CC=1)C)=CC=1C(=O)NC1(C=2NC3=CC=NC=C3N=2)CC1 OERSXZVIJIUUCT-UHFFFAOYSA-N 0.000 claims 1
- LBUFUCLDHUACQQ-UHFFFAOYSA-N 4-fluoro-2-(4-fluorophenyl)-5-[5-[[1-(3h-imidazo[4,5-c]pyridin-2-yl)cyclopropyl]carbamoyl]-4-methoxy-2-methylphenyl]-n-methyl-1-benzofuran-3-carboxamide Chemical compound FC1=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=CC=C1C(C(=CC=1OC)C)=CC=1C(=O)NC1(C=2NC3=CC=NC=C3N=2)CC1 LBUFUCLDHUACQQ-UHFFFAOYSA-N 0.000 claims 1
- VDNLVFOSNVVOID-UHFFFAOYSA-N 4-fluoro-2-(4-fluorophenyl)-n-methyl-5-[2-methyl-5-[[1-(1,5-naphthyridin-2-yl)cyclopropyl]carbamoyl]phenyl]-1-benzofuran-3-carboxamide Chemical compound FC1=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=CC=C1C(C(=CC=1)C)=CC=1C(=O)NC1(C=2N=C3C=CC=NC3=CC=2)CC1 VDNLVFOSNVVOID-UHFFFAOYSA-N 0.000 claims 1
- NFWJVZCHHBVHHO-UHFFFAOYSA-N 4-fluoro-2-(4-fluorophenyl)-n-methyl-5-[2-methyl-5-[[1-(1,6-naphthyridin-2-yl)cyclopropyl]carbamoyl]phenyl]-1-benzofuran-3-carboxamide Chemical compound FC1=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=CC=C1C(C(=CC=1)C)=CC=1C(=O)NC1(C=2N=C3C=CN=CC3=CC=2)CC1 NFWJVZCHHBVHHO-UHFFFAOYSA-N 0.000 claims 1
- WPNSUWPSDTWZLK-UHFFFAOYSA-N 4-fluoro-2-(4-fluorophenyl)-n-methyl-5-[2-methyl-5-[[1-(1,7-naphthyridin-2-yl)cyclopropyl]carbamoyl]phenyl]-1-benzofuran-3-carboxamide Chemical compound FC1=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=CC=C1C(C(=CC=1)C)=CC=1C(=O)NC1(C=2N=C3C=NC=CC3=CC=2)CC1 WPNSUWPSDTWZLK-UHFFFAOYSA-N 0.000 claims 1
- RXYMNVJZUGDQRS-UHFFFAOYSA-N 4-fluoro-2-(4-fluorophenyl)-n-methyl-5-[2-methyl-5-[[1-(1,8-naphthyridin-2-yl)cyclopropyl]carbamoyl]phenyl]-1-benzofuran-3-carboxamide Chemical compound FC1=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=CC=C1C(C(=CC=1)C)=CC=1C(=O)NC1(C=2N=C3N=CC=CC3=CC=2)CC1 RXYMNVJZUGDQRS-UHFFFAOYSA-N 0.000 claims 1
- YMMNOYIJDISYRV-UHFFFAOYSA-N 4-fluoro-2-(4-fluorophenyl)-n-methyl-5-[2-methyl-5-[[1-(1h-pyrrolo[3,2-b]pyridin-5-yl)cyclopropyl]carbamoyl]phenyl]-1-benzofuran-3-carboxamide Chemical compound FC1=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=CC=C1C(C(=CC=1)C)=CC=1C(=O)NC1(C=2N=C3C=CNC3=CC=2)CC1 YMMNOYIJDISYRV-UHFFFAOYSA-N 0.000 claims 1
- LEGGFTCFMDFJSS-UHFFFAOYSA-N 4-fluoro-2-(4-fluorophenyl)-n-methyl-5-[2-methyl-5-[[1-(1h-pyrrolo[3,2-c]pyridin-4-yl)cyclopropyl]carbamoyl]phenyl]-1-benzofuran-3-carboxamide Chemical compound FC1=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=CC=C1C(C(=CC=1)C)=CC=1C(=O)NC1(C=2C=3C=CNC=3C=CN=2)CC1 LEGGFTCFMDFJSS-UHFFFAOYSA-N 0.000 claims 1
- ITDFFNLBFGSOLB-MRXNPFEDSA-N 4-fluoro-5-[3-fluoro-2-methyl-5-[[(1r)-1-([1,3]oxazolo[4,5-c]pyridin-2-yl)ethyl]carbamoyl]phenyl]-2-(4-fluorophenyl)-n-methyl-1-benzofuran-3-carboxamide Chemical compound O1C2=CC=C(C=3C(=C(F)C=C(C=3)C(=O)N[C@H](C)C=3OC4=CC=NC=C4N=3)C)C(F)=C2C(C(=O)NC)=C1C1=CC=C(F)C=C1 ITDFFNLBFGSOLB-MRXNPFEDSA-N 0.000 claims 1
- ITDFFNLBFGSOLB-INIZCTEOSA-N 4-fluoro-5-[3-fluoro-2-methyl-5-[[(1s)-1-([1,3]oxazolo[4,5-c]pyridin-2-yl)ethyl]carbamoyl]phenyl]-2-(4-fluorophenyl)-n-methyl-1-benzofuran-3-carboxamide Chemical compound O1C2=CC=C(C=3C(=C(F)C=C(C=3)C(=O)N[C@@H](C)C=3OC4=CC=NC=C4N=3)C)C(F)=C2C(C(=O)NC)=C1C1=CC=C(F)C=C1 ITDFFNLBFGSOLB-INIZCTEOSA-N 0.000 claims 1
- ONWPMBHQPKIFRV-UHFFFAOYSA-N 4-fluoro-5-[3-fluoro-2-methyl-5-[[1-([1,3]oxazolo[4,5-c]pyridin-2-yl)cyclopropyl]carbamoyl]phenyl]-2-(4-fluorophenyl)-n-methyl-1-benzofuran-3-carboxamide Chemical compound FC1=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=CC=C1C(C(=C(F)C=1)C)=CC=1C(=O)NC1(C=2OC3=CC=NC=C3N=2)CC1 ONWPMBHQPKIFRV-UHFFFAOYSA-N 0.000 claims 1
- FOFFRLQZFIMTJX-UHFFFAOYSA-N 4-fluoro-5-[3-fluoro-5-[[1-(3h-imidazo[4,5-c]pyridin-2-yl)cyclopropyl]carbamoyl]-2-methylphenyl]-2-(4-fluorophenyl)-n-methyl-1-benzofuran-3-carboxamide Chemical compound FC1=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=CC=C1C(C(=C(F)C=1)C)=CC=1C(=O)NC1(C=2NC3=CC=NC=C3N=2)CC1 FOFFRLQZFIMTJX-UHFFFAOYSA-N 0.000 claims 1
- DODKVWTYKYIFKH-UHFFFAOYSA-N 5-[2-(2-amino-2-oxoethoxy)-4-methoxy-5-[[1-(1,7-naphthyridin-2-yl)cyclopropyl]carbamoyl]phenyl]-2-(4-fluorophenyl)-n-methyl-1-benzofuran-3-carboxamide Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=CC=C1C(C(=CC=1OC)OCC(N)=O)=CC=1C(=O)NC1(C=2N=C3C=NC=CC3=CC=2)CC1 DODKVWTYKYIFKH-UHFFFAOYSA-N 0.000 claims 1
- 108020005544 Antisense RNA Proteins 0.000 claims 1
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 claims 1
- 108010036949 Cyclosporine Proteins 0.000 claims 1
- 102000014150 Interferons Human genes 0.000 claims 1
- 108010050904 Interferons Proteins 0.000 claims 1
- 102000013462 Interleukin-12 Human genes 0.000 claims 1
- 108010065805 Interleukin-12 Proteins 0.000 claims 1
- 102000000588 Interleukin-2 Human genes 0.000 claims 1
- 108010002350 Interleukin-2 Proteins 0.000 claims 1
- 102000004889 Interleukin-6 Human genes 0.000 claims 1
- 108090001005 Interleukin-6 Proteins 0.000 claims 1
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 claims 1
- 230000005867 T cell response Effects 0.000 claims 1
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 claims 1
- 229960003805 amantadine Drugs 0.000 claims 1
- 229960001265 ciclosporin Drugs 0.000 claims 1
- 239000003184 complementary RNA Substances 0.000 claims 1
- 229930182912 cyclosporin Natural products 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 210000002443 helper t lymphocyte Anatomy 0.000 claims 1
- DOUYETYNHWVLEO-UHFFFAOYSA-N imiquimod Chemical compound C1=CC=CC2=C3N(CC(C)C)C=NC3=C(N)N=C21 DOUYETYNHWVLEO-UHFFFAOYSA-N 0.000 claims 1
- 229960002751 imiquimod Drugs 0.000 claims 1
- 239000002348 inosinate dehydrogenase inhibitor Substances 0.000 claims 1
- 230000002452 interceptive effect Effects 0.000 claims 1
- 229940079322 interferon Drugs 0.000 claims 1
- 229940117681 interleukin-12 Drugs 0.000 claims 1
- 229940100601 interleukin-6 Drugs 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 229960000329 ribavirin Drugs 0.000 claims 1
- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 claims 1
- 229960000888 rimantadine Drugs 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31276810P | 2010-03-11 | 2010-03-11 | |
| US61/312,768 | 2010-03-11 | ||
| US13/043,747 | 2011-03-09 | ||
| US13/043,747 US8354410B2 (en) | 2010-03-11 | 2011-03-09 | Compounds for the treatment of hepatitis C |
| PCT/US2011/027823 WO2011112769A1 (en) | 2010-03-11 | 2011-03-10 | Compounds for the treatment of hepatitis c |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013522224A JP2013522224A (ja) | 2013-06-13 |
| JP2013522224A5 true JP2013522224A5 (enExample) | 2014-05-01 |
| JP5735551B2 JP5735551B2 (ja) | 2015-06-17 |
Family
ID=43903118
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012557233A Expired - Fee Related JP5735551B2 (ja) | 2010-03-11 | 2011-03-10 | Ｃ型肝炎の処置のための化合物 |
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| EP (1) | EP2545051B1 (enExample) |
| JP (1) | JP5735551B2 (enExample) |
| KR (1) | KR20130016263A (enExample) |
| CN (1) | CN102892767A (enExample) |
| AU (1) | AU2011224319A1 (enExample) |
| MX (1) | MX2012010216A (enExample) |
| WO (1) | WO2011112769A1 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5731004B2 (ja) | 2010-10-26 | 2015-06-10 | プレシディオ ファーマシューティカルズ インコーポレイテッド | Ｃ型肝炎ウイルスの阻害剤 |
| US8507683B2 (en) | 2010-12-09 | 2013-08-13 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| US9303020B2 (en) | 2012-02-08 | 2016-04-05 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| JP2016505011A (ja) * | 2013-01-10 | 2016-02-18 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | Ｃ型肝炎の治療用の大環状ベンゾフランおよびアザベンゾフラン化合物 |
| JP6423372B2 (ja) | 2013-02-28 | 2018-11-14 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | 強力なｒｏｃｋ１およびｒｏｃｋ２阻害剤としてのフェニルピラゾール誘導体 |
| AR094929A1 (es) | 2013-02-28 | 2015-09-09 | Bristol Myers Squibb Co | Derivados de fenilpirazol como inhibidores potentes de rock1 y rock2 |
| WO2014205592A1 (en) | 2013-06-24 | 2014-12-31 | Merck Sharp & Dohme Corp. | Heterocyclic compounds and methods of use thereof for treatment of hepatitis c |
| WO2014205594A1 (en) * | 2013-06-24 | 2014-12-31 | Merck Sharp & Dohme Corp. | Substituted benzofuran compounds and methods of use thereof for treatment of viral diseases |
| US9920036B2 (en) * | 2014-03-21 | 2018-03-20 | Bristol-Myers Squibb Company | Cyanoamino (aza)benzofuran compounds for the treatment of hepatitis C |
| CN105732602B (zh) * | 2015-09-23 | 2017-04-19 | 常州寅盛药业有限公司 | 作为ns4b抑制剂的苯并呋喃类似物 |
| CN114957110A (zh) * | 2021-02-26 | 2022-08-30 | 清华大学 | 一种抗病毒化合物及其制备方法和应用 |
| JP2025514293A (ja) * | 2022-04-29 | 2025-05-02 | 清華大学 | ＰＬｐｒｏタンパク質阻害剤、その製造方法、及び使用 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57123181A (en) | 1981-01-23 | 1982-07-31 | Mitsubishi Paper Mills Ltd | Preparation of pyrazolo (1,5-a) pyridine derivative |
| EE200100341A (et) * | 1998-12-24 | 2002-12-16 | Aventis Pharmaceuticals Products Inc. | Asendatud (aminoiminometüül- või aminometüül)bensoheteroarüülühendid, nende kasutamine ja farmatseutiline kompositsioon |
| PE20020506A1 (es) | 2000-08-22 | 2002-07-09 | Glaxo Group Ltd | Derivados de pirazol fusionados como inhibidores de la proteina cinasa |
| JP2004525150A (ja) | 2001-03-30 | 2004-08-19 | スミスクライン ビーチャム コーポレーション | 治療用化合物としてのピラゾロピリジン類の使用 |
| WO2004041201A2 (en) | 2002-11-01 | 2004-05-21 | Viropharma Incorporated | Benzofuran compounds, compositions and methods for treatment and prophylaxis of hepatitis c viral infections and associated diseases |
| US7868037B2 (en) | 2004-07-14 | 2011-01-11 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
| JP2010518125A (ja) * | 2007-02-12 | 2010-05-27 | インターミューン・インコーポレーテッド | Ｃ型肝炎ウイルス複製の新規な阻害剤 |
| GB0707000D0 (en) | 2007-04-12 | 2007-05-30 | Istituto Di Ricerche D Biolog | Antiviral agents |
| EP2245023B1 (en) | 2008-02-14 | 2011-12-28 | F. Hoffmann-La Roche AG | Heterocyclic antiviral compounds |
| WO2009137500A1 (en) | 2008-05-05 | 2009-11-12 | Wyeth | 6-substituted benzofuran compounds to treat infection with hepatitis c virus |
| WO2009137493A1 (en) | 2008-05-05 | 2009-11-12 | Wyeth | 2-substituted benzofuran compounds to treat infection with hepatitis c virus |
| US8048887B2 (en) | 2008-09-11 | 2011-11-01 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| US8198449B2 (en) | 2008-09-11 | 2012-06-12 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| US7994171B2 (en) * | 2008-09-11 | 2011-08-09 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| AR080185A1 (es) | 2010-02-19 | 2012-03-21 | Glaxo Group Ltd | Derivados de acido boronico y benzofurano, composiciones farmaceuticas que los contienen,y uso de los mismos en el tratamiento y/o prevencion de infecciones virales, en particular por el virus de hepatitis c(hcv). |
| HUE032620T2 (en) | 2010-03-01 | 2017-10-30 | Plascoenergy Ip Holdings S L Bilbao Schaffhausen Branch | Module for use with lateral delivery system |
| TW201136919A (en) | 2010-03-02 | 2011-11-01 | Merck Sharp & Amp Dohme Corp | Inhibitors of hepatitis C virus NS5B polymerase |
| WO2011106929A1 (en) | 2010-03-02 | 2011-09-09 | Merck Sharp & Dohme Corp. | Inhibitors of hepatitis c virus ns5b polymerase |
-
2011
- 2011-03-09 US US13/043,747 patent/US8354410B2/en active Active
- 2011-03-10 EP EP11708667.8A patent/EP2545051B1/en not_active Not-in-force
- 2011-03-10 WO PCT/US2011/027823 patent/WO2011112769A1/en not_active Ceased
- 2011-03-10 AU AU2011224319A patent/AU2011224319A1/en not_active Abandoned
- 2011-03-10 JP JP2012557233A patent/JP5735551B2/ja not_active Expired - Fee Related
- 2011-03-10 MX MX2012010216A patent/MX2012010216A/es active IP Right Grant
- 2011-03-10 KR KR1020127026466A patent/KR20130016263A/ko not_active Withdrawn
- 2011-03-10 CN CN2011800236466A patent/CN102892767A/zh active Pending
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