JP2012523457A5 - - Google Patents
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- Publication number
- JP2012523457A5 JP2012523457A5 JP2012506080A JP2012506080A JP2012523457A5 JP 2012523457 A5 JP2012523457 A5 JP 2012523457A5 JP 2012506080 A JP2012506080 A JP 2012506080A JP 2012506080 A JP2012506080 A JP 2012506080A JP 2012523457 A5 JP2012523457 A5 JP 2012523457A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- hydrogen
- pharmaceutically acceptable
- acceptable salt
- formula
- 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 29
- 229910052739 hydrogen Inorganic materials 0.000 claims 27
- 239000001257 hydrogen Substances 0.000 claims 27
- 150000003839 salts Chemical class 0.000 claims 22
- 125000000217 alkyl group Chemical group 0.000 claims 21
- 150000002431 hydrogen Chemical class 0.000 claims 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 11
- 125000000623 heterocyclic group Chemical group 0.000 claims 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims 10
- 125000003118 aryl group Chemical group 0.000 claims 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims 10
- 229910052736 halogen Inorganic materials 0.000 claims 10
- 150000002367 halogens Chemical class 0.000 claims 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 9
- -1 —NR a R b Chemical group 0.000 claims 9
- 125000001072 heteroaryl group Chemical group 0.000 claims 8
- 125000001424 substituent group Chemical group 0.000 claims 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- 125000001188 haloalkyl group Chemical group 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 239000001301 oxygen Substances 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 239000011593 sulfur Substances 0.000 claims 3
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 2
- 108091032973 (ribonucleotides)n+m Proteins 0.000 claims 2
- UBCHPRBFMUDMNC-UHFFFAOYSA-N 1-(1-adamantyl)ethanamine Chemical compound C1C(C2)CC3CC2CC1(C(N)C)C3 UBCHPRBFMUDMNC-UHFFFAOYSA-N 0.000 claims 2
- 108020005544 Antisense RNA Proteins 0.000 claims 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 2
- 102000014150 Interferons Human genes 0.000 claims 2
- 108010050904 Interferons Proteins 0.000 claims 2
- 102000000588 Interleukin-2 Human genes 0.000 claims 2
- 108010002350 Interleukin-2 Proteins 0.000 claims 2
- 102000004889 Interleukin-6 Human genes 0.000 claims 2
- 108090001005 Interleukin-6 Proteins 0.000 claims 2
- 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 2
- 230000005867 T cell response Effects 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 claims 2
- 229960003805 amantadine Drugs 0.000 claims 2
- 125000002619 bicyclic group Chemical group 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 239000003184 complementary RNA Substances 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 210000002443 helper t lymphocyte Anatomy 0.000 claims 2
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 2
- 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 2
- 229960002751 imiquimod Drugs 0.000 claims 2
- 208000015181 infectious disease Diseases 0.000 claims 2
- 239000002348 inosinate dehydrogenase inhibitor Substances 0.000 claims 2
- 230000002452 interceptive effect Effects 0.000 claims 2
- 229940079322 interferon Drugs 0.000 claims 2
- 229940100601 interleukin-6 Drugs 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 229960000329 ribavirin Drugs 0.000 claims 2
- 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 2
- 229960000888 rimantadine Drugs 0.000 claims 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 102000013462 Interleukin-12 Human genes 0.000 claims 1
- 108010065805 Interleukin-12 Proteins 0.000 claims 1
- 102000015696 Interleukins Human genes 0.000 claims 1
- 108010063738 Interleukins Proteins 0.000 claims 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000005605 benzo group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 229940117681 interleukin-12 Drugs 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 125000006501 nitrophenyl group Chemical group 0.000 claims 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims 1
- NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 0 CC(*)c1ncc(C=*(C)C)[n]1 Chemical compound CC(*)c1ncc(C=*(C)C)[n]1 0.000 description 10
- LDZYRENCLPUXAX-UHFFFAOYSA-N Cc1nc(cccc2)c2[nH]1 Chemical compound Cc1nc(cccc2)c2[nH]1 LDZYRENCLPUXAX-UHFFFAOYSA-N 0.000 description 3
- MPZVYLVNGUIBGY-UHFFFAOYSA-N CC1(C)SC=NC=C1 Chemical compound CC1(C)SC=NC=C1 MPZVYLVNGUIBGY-UHFFFAOYSA-N 0.000 description 1
- BBWGRAJHKBOHBU-UHFFFAOYSA-O CC[NH2+]C=NC=C Chemical compound CC[NH2+]C=NC=C BBWGRAJHKBOHBU-UHFFFAOYSA-O 0.000 description 1
- JHKKTXXMAQLGJB-UHFFFAOYSA-N CNc1ccccc1O Chemical compound CNc1ccccc1O JHKKTXXMAQLGJB-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16889109P | 2009-04-13 | 2009-04-13 | |
| US61/168,891 | 2009-04-13 | ||
| PCT/US2010/030366 WO2010120621A1 (en) | 2009-04-13 | 2010-04-08 | Hepatitis c virus inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012523457A JP2012523457A (ja) | 2012-10-04 |
| JP2012523457A5 true JP2012523457A5 (cg-RX-API-DMAC10.html) | 2013-03-28 |
| JP5558557B2 JP5558557B2 (ja) | 2014-07-23 |
Family
ID=42194782
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012506080A Expired - Fee Related JP5558557B2 (ja) | 2009-04-13 | 2010-04-08 | Ｃ型肝炎ウイルス阻害剤 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US8143414B2 (cg-RX-API-DMAC10.html) |
| EP (1) | EP2419433B1 (cg-RX-API-DMAC10.html) |
| JP (1) | JP5558557B2 (cg-RX-API-DMAC10.html) |
| CN (1) | CN102459281B (cg-RX-API-DMAC10.html) |
| WO (1) | WO2010120621A1 (cg-RX-API-DMAC10.html) |
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2010
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- 2010-04-08 EP EP10714135.0A patent/EP2419433B1/en not_active Not-in-force
- 2010-04-08 JP JP2012506080A patent/JP5558557B2/ja not_active Expired - Fee Related
- 2010-04-08 WO PCT/US2010/030366 patent/WO2010120621A1/en not_active Ceased
- 2010-04-08 CN CN201080027402.0A patent/CN102459281B/zh not_active Expired - Fee Related