JP2013510857A5 - - Google Patents
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- Publication number
- JP2013510857A5 JP2013510857A5 JP2012538923A JP2012538923A JP2013510857A5 JP 2013510857 A5 JP2013510857 A5 JP 2013510857A5 JP 2012538923 A JP2012538923 A JP 2012538923A JP 2012538923 A JP2012538923 A JP 2012538923A JP 2013510857 A5 JP2013510857 A5 JP 2013510857A5
- Authority
- JP
- Japan
- Prior art keywords
- imidazol
- pyrrolidinyl
- methyl
- alkyl
- 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
Links
- -1 —NR a R b Chemical group 0.000 claims 35
- 125000000217 alkyl group Chemical group 0.000 claims 31
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 27
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 26
- 229910052739 hydrogen Inorganic materials 0.000 claims 20
- 239000001257 hydrogen Substances 0.000 claims 20
- 125000003118 aryl group Chemical group 0.000 claims 17
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 17
- 150000001875 compounds Chemical class 0.000 claims 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims 14
- 150000003839 salts Chemical class 0.000 claims 14
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 12
- 125000000623 heterocyclic group Chemical group 0.000 claims 12
- 125000001424 substituent group Chemical group 0.000 claims 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 10
- 125000001072 heteroaryl group Chemical group 0.000 claims 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims 9
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 9
- 150000002431 hydrogen Chemical class 0.000 claims 8
- 229910052757 nitrogen Inorganic materials 0.000 claims 8
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 7
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 125000003342 alkenyl group Chemical group 0.000 claims 6
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 6
- 229920002554 vinyl polymer Polymers 0.000 claims 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000001188 haloalkyl group Chemical group 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 239000011593 sulfur Substances 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
- AOGFRXVTKLIGBI-UHFFFAOYSA-N 2-(dimethylamino)-2-phenylacetaldehyde Chemical compound CN(C)C(C=O)C1=CC=CC=C1 AOGFRXVTKLIGBI-UHFFFAOYSA-N 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 125000002619 bicyclic group Chemical group 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 2
- 208000015181 infectious disease Diseases 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- OSENLJXQFXDBAW-XITCCLNHSA-N (2r)-2-(dimethylamino)-1-[(2s)-2-[5-[2-[5-[2-[(2s)-1-[(2r)-2-(dimethylamino)-2-phenylacetyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]-1,3-thiazol-2-yl]-1,3-thiazol-5-yl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-phenylethanone Chemical compound C1([C@@H](N(C)C)C(=O)N2CCC[C@H]2C=2NC=C(N=2)C2=CN=C(S2)C2=NC=C(S2)C=2N=C(NC=2)[C@@H]2CCCN2C(=O)[C@H](N(C)C)C=2C=CC=CC=2)=CC=CC=C1 OSENLJXQFXDBAW-XITCCLNHSA-N 0.000 claims 1
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 1
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
- 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
- JUJYNCPRVMVRCV-LURJTMIESA-N 2-[(2s)-pyrrolidin-2-yl]-1h-imidazole Chemical compound C1CCN[C@@H]1C1=NC=CN1 JUJYNCPRVMVRCV-LURJTMIESA-N 0.000 claims 1
- FEMGDABWOYOLHX-RYUDHWBXSA-N 2-[2-[(2s)-pyrrolidin-2-yl]-1h-imidazol-5-yl]-5-[2-[2-[(2s)-pyrrolidin-2-yl]-1h-imidazol-5-yl]-1,3-thiazol-5-yl]-1,3-thiazole Chemical compound C1CCN[C@@H]1C1=NC=C(C=2SC(=CN=2)C=2SC(=NC=2)C=2NC(=NC=2)[C@H]2NCCC2)N1 FEMGDABWOYOLHX-RYUDHWBXSA-N 0.000 claims 1
- FIYUKWDVNOJKHT-UHFFFAOYSA-N 2-phenyl-2-piperidin-1-ylacetaldehyde Chemical compound C=1C=CC=CC=1C(C=O)N1CCCCC1 FIYUKWDVNOJKHT-UHFFFAOYSA-N 0.000 claims 1
- ZFIFEBBUIKTZKS-RYUDHWBXSA-N 5-[2-[(2s)-pyrrolidin-2-yl]-1h-imidazol-5-yl]-2-[5-[2-[(2s)-pyrrolidin-2-yl]-1h-imidazol-5-yl]-1,3-thiazol-2-yl]-1,3-thiazole Chemical compound C1CCN[C@@H]1C1=NC(C=2SC(=NC=2)C=2SC(=CN=2)C=2N=C(NC=2)[C@H]2NCCC2)=CN1 ZFIFEBBUIKTZKS-RYUDHWBXSA-N 0.000 claims 1
- 108020005544 Antisense RNA 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
- AMNPXXIGUOKIPP-UHFFFAOYSA-N [4-(carbamothioylamino)phenyl]thiourea Chemical compound NC(=S)NC1=CC=C(NC(N)=S)C=C1 AMNPXXIGUOKIPP-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 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
- HIWVUBQPVDKVGD-IXQHYERASA-N benzyl (2s)-2-[5-[5-[4-[2-[(2s)-1-[(2r)-2-(dimethylamino)-2-phenylacetyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]-1,3-oxazol-2-yl]-1h-imidazol-2-yl]pyrrolidine-1-carboxylate Chemical compound C([C@H]1C=2NC=C(N=2)C2=NC=C(O2)C2=CC=C(C=C2)C=2N=C(NC=2)[C@@H]2CCCN2C(=O)[C@H](N(C)C)C=2C=CC=CC=2)CCN1C(=O)OCC1=CC=CC=C1 HIWVUBQPVDKVGD-IXQHYERASA-N 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- FKBJETAMOYHENX-UHFFFAOYSA-N carbamoyl 2-carbamoyloxy-2-phenylacetate Chemical compound C(N)(OC(C(C1=CC=CC=C1)OC(N)=O)=O)=O FKBJETAMOYHENX-UHFFFAOYSA-N 0.000 claims 1
- AZHCBEAXMJJJIQ-UHFFFAOYSA-N carbamoyl 2-carbamoyloxy-3-methylbutanoate Chemical compound C(N)(OC(C(=O)OC(N)=O)C(C)C)=O AZHCBEAXMJJJIQ-UHFFFAOYSA-N 0.000 claims 1
- FLQQVZUEGGIEBT-UHFFFAOYSA-N carbamoyl 2-carbamoyloxypropanoate Chemical compound C(N)(OC(C(=O)OC(N)=O)C)=O FLQQVZUEGGIEBT-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000003184 complementary RNA Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 210000002443 helper t lymphocyte Anatomy 0.000 claims 1
- 125000005842 heteroatom Chemical group 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
- XXJIIQQLIKDFDN-CNXCYTMISA-N methyl n-[(2r)-1-[(2s)-2-[5-[5-[2-[2-[(2s)-1-[(2r)-2-(methoxycarbonylamino)-3-methylbutanoyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]-1,3-thiazol-5-yl]-1,3-thiazol-2-yl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamate Chemical compound COC(=O)N[C@H](C(C)C)C(=O)N1CCC[C@H]1C1=NC=C(C=2SC(=CN=2)C=2SC(=NC=2)C=2NC(=NC=2)[C@H]2N(CCC2)C(=O)[C@H](NC(=O)OC)C(C)C)N1 XXJIIQQLIKDFDN-CNXCYTMISA-N 0.000 claims 1
- XXJIIQQLIKDFDN-JPMIEVGJSA-N methyl n-[(2s)-1-[(2s)-2-[5-[5-[2-[2-[(2s)-1-[(2s)-2-(methoxycarbonylamino)-3-methylbutanoyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]-1,3-thiazol-5-yl]-1,3-thiazol-2-yl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C1=NC=C(C=2SC(=CN=2)C=2SC(=NC=2)C=2NC(=NC=2)[C@H]2N(CCC2)C(=O)[C@@H](NC(=O)OC)C(C)C)N1 XXJIIQQLIKDFDN-JPMIEVGJSA-N 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 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
- XOZUXKDVWIRGBA-PMACEKPBSA-N tert-butyl (2s)-2-[5-[2-[5-[2-[(2s)-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]-1,3-thiazol-2-yl]-1,3-thiazol-5-yl]-1h-imidazol-2-yl]pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC[C@H]1C1=NC=C(C=2SC(=NC=2)C=2SC(=CN=2)C=2N=C(NC=2)[C@H]2N(CCC2)C(=O)OC(C)(C)C)N1 XOZUXKDVWIRGBA-PMACEKPBSA-N 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US26056909P | 2009-11-12 | 2009-11-12 | |
| US61/260,569 | 2009-11-12 | ||
| US12/942,183 US20110281910A1 (en) | 2009-11-12 | 2010-11-09 | Hepatitis C Virus Inhibitors |
| US12/942,183 | 2010-11-09 | ||
| PCT/US2010/056114 WO2011060000A1 (en) | 2009-11-12 | 2010-11-10 | Hepatitis c virus inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013510857A JP2013510857A (ja) | 2013-03-28 |
| JP2013510857A5 true JP2013510857A5 (https=) | 2013-12-05 |
| JP5697679B2 JP5697679B2 (ja) | 2015-04-08 |
Family
ID=43334735
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012538923A Expired - Fee Related JP5697679B2 (ja) | 2009-11-12 | 2010-11-10 | Ｃ型肝炎ウイルス阻害剤 |
Country Status (5)
| Country | Link |
|---|---|
| US (3) | US20110281910A1 (https=) |
| EP (1) | EP2499132B1 (https=) |
| JP (1) | JP5697679B2 (https=) |
| CN (1) | CN102712628B (https=) |
| WO (1) | WO2011060000A1 (https=) |
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| PT3309157T (pt) | 2009-05-13 | 2019-12-02 | Gilead Pharmasset Llc | Compostos antivirais |
| US8138215B2 (en) | 2009-05-29 | 2012-03-20 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8211928B2 (en) | 2009-05-29 | 2012-07-03 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
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| US20110274648A1 (en) | 2009-11-11 | 2011-11-10 | Bristol-Myers Squibb Company | Hepatitis C Virus Inhibitors |
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| CA2862755A1 (en) | 2012-02-10 | 2013-08-15 | Lupin Limited | Antiviral compounds with a dibenzooxaheterocycle moiety |
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-
2010
- 2010-11-09 US US12/942,183 patent/US20110281910A1/en not_active Abandoned
- 2010-11-10 EP EP10779401.8A patent/EP2499132B1/en not_active Not-in-force
- 2010-11-10 JP JP2012538923A patent/JP5697679B2/ja not_active Expired - Fee Related
- 2010-11-10 WO PCT/US2010/056114 patent/WO2011060000A1/en not_active Ceased
- 2010-11-10 CN CN201080061374.4A patent/CN102712628B/zh not_active Expired - Fee Related
-
2012
- 2012-09-12 US US13/611,708 patent/US8618153B2/en active Active
-
2013
- 2013-09-16 US US14/027,531 patent/US20140018389A1/en not_active Abandoned
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