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 US8354410B2 (en) | 2010-03-11 | 2011-03-09 | Compounds for the treatment of hepatitis C |
| US13/043,747 | 2011-03-09 | ||
| 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 (https=) | 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 (https=) |
| JP (1) | JP5735551B2 (https=) |
| KR (1) | KR20130016263A (https=) |
| CN (1) | CN102892767A (https=) |
| AU (1) | AU2011224319A1 (https=) |
| MX (1) | MX2012010216A (https=) |
| WO (1) | WO2011112769A1 (https=) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG189985A1 (en) | 2010-10-26 | 2013-06-28 | Presidio Pharmaceuticals Inc | Inhibitors of hepatitis c virus |
| 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 |
| US9434738B2 (en) | 2013-01-10 | 2016-09-06 | Bristol-Myers Squibb Company | Macrocyclic benzofuran and azabenzofuran compounds for the treatment of hepatitis C |
| CN105102448B (zh) | 2013-02-28 | 2018-03-06 | 百时美施贵宝公司 | 作为rock1和rock2抑制剂的苯基吡唑衍生物 |
| 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 |
| CN114957110B (zh) * | 2021-02-26 | 2026-04-21 | 清华大学 | 一种抗病毒化合物及其制备方法和应用 |
| CN116969941A (zh) * | 2022-04-29 | 2023-10-31 | 清华大学 | PLpro蛋白抑制剂及其制备方法和应用 |
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 |
| CA2358047A1 (en) * | 1998-12-24 | 2000-07-06 | Francis A. Volz | Substituted (aminoiminomethyl or aminomethyl)benzoheteroaryl compounds |
| PE20020506A1 (es) | 2000-08-22 | 2002-07-09 | Glaxo Group Ltd | Derivados de pirazol fusionados como inhibidores de la proteina cinasa |
| WO2002078701A1 (en) | 2001-03-30 | 2002-10-10 | Smithkline Beecham Corporation | Use of pyrazolopyridines as therapeutic compounds |
| EA009943B1 (ru) * | 2002-11-01 | 2008-04-28 | Вирофарма Инкорпорейтед | Соединения бензофурана, композиции и способы лечения и профилактики инфекций, вызванных вирусом гепатита с, и связанных с ним заболеваний |
| US7868037B2 (en) | 2004-07-14 | 2011-01-11 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
| MX2009008439A (es) * | 2007-02-12 | 2009-08-13 | Intermune Inc | Nuevos inhibidores de la replicacion del virus de hepatitis c. |
| GB0707000D0 (en) | 2007-04-12 | 2007-05-30 | Istituto Di Ricerche D Biolog | Antiviral agents |
| ATE539070T1 (de) | 2008-02-14 | 2012-01-15 | Hoffmann La Roche | Heterozyklische antivirale verbindungen |
| 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 |
| WO2011103063A1 (en) | 2010-02-19 | 2011-08-25 | Glaxo Group Limited | Therapeutic compounds |
| US20120067257A1 (en) | 2010-03-01 | 2012-03-22 | Plasco Energy Group. Inc. | A Lateral Transfer System |
| WO2011106929A1 (en) | 2010-03-02 | 2011-09-09 | Merck Sharp & Dohme Corp. | Inhibitors of hepatitis c virus ns5b polymerase |
| TW201136919A (en) | 2010-03-02 | 2011-11-01 | Merck Sharp & Amp 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 MX MX2012010216A patent/MX2012010216A/es active IP Right Grant
- 2011-03-10 CN CN2011800236466A patent/CN102892767A/zh active Pending
- 2011-03-10 AU AU2011224319A patent/AU2011224319A1/en not_active Abandoned
- 2011-03-10 WO PCT/US2011/027823 patent/WO2011112769A1/en not_active Ceased
- 2011-03-10 JP JP2012557233A patent/JP5735551B2/ja not_active Expired - Fee Related
- 2011-03-10 EP EP11708667.8A patent/EP2545051B1/en not_active Not-in-force
- 2011-03-10 KR KR1020127026466A patent/KR20130016263A/ko not_active Withdrawn
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