JP2012528166A5 - - Google Patents
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- Publication number
- JP2012528166A5 JP2012528166A5 JP2012513170A JP2012513170A JP2012528166A5 JP 2012528166 A5 JP2012528166 A5 JP 2012528166A5 JP 2012513170 A JP2012513170 A JP 2012513170A JP 2012513170 A JP2012513170 A JP 2012513170A JP 2012528166 A5 JP2012528166 A5 JP 2012528166A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- hydrogen
- pharmaceutically acceptable
- independently selected
- acceptable salt
- 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 36
- 229910052739 hydrogen Inorganic materials 0.000 claims 34
- 239000001257 hydrogen Substances 0.000 claims 34
- 150000002431 hydrogen Chemical class 0.000 claims 23
- 150000001875 compounds Chemical class 0.000 claims 21
- 150000003839 salts Chemical class 0.000 claims 19
- 125000003710 aryl alkyl group Chemical group 0.000 claims 17
- 125000003118 aryl group Chemical group 0.000 claims 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims 15
- 125000000623 heterocyclic group Chemical group 0.000 claims 15
- 229910052736 halogen Inorganic materials 0.000 claims 13
- 150000002367 halogens Chemical class 0.000 claims 13
- 125000001072 heteroaryl group Chemical group 0.000 claims 12
- 125000001424 substituent group Chemical group 0.000 claims 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 11
- -1 —NR a R b Chemical group 0.000 claims 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 5
- 125000001188 haloalkyl group Chemical group 0.000 claims 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 239000001301 oxygen Substances 0.000 claims 5
- VLJNHYLEOZPXFW-UHFFFAOYSA-N pyrrolidine-2-carboxamide Chemical compound NC(=O)C1CCCN1 VLJNHYLEOZPXFW-UHFFFAOYSA-N 0.000 claims 5
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims 4
- 125000002619 bicyclic group Chemical group 0.000 claims 4
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 208000015181 infectious disease Diseases 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 229910052717 sulfur Chemical group 0.000 claims 2
- 239000011593 sulfur Chemical group 0.000 claims 2
- JXCVMJKEIAJDTR-PMACEKPBSA-N (2s)-n-[5-[4-[2-[(2s)-pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]-1,2-benzoxazol-3-yl]pyrrolidine-2-carboxamide Chemical compound O=C([C@H]1NCCC1)NC(C1=C2)=NOC1=CC=C2C(C=C1)=CC=C1C(N1)=CN=C1[C@@H]1CCCN1 JXCVMJKEIAJDTR-PMACEKPBSA-N 0.000 claims 1
- YFWSCHXAXPPKRF-SFTDATJTSA-N (2s)-n-[5-[4-[2-[(2s)-pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]-1h-indazol-3-yl]pyrrolidine-2-carboxamide Chemical compound O=C([C@H]1NCCC1)NC(C1=C2)=NNC1=CC=C2C(C=C1)=CC=C1C(N1)=CN=C1[C@@H]1CCCN1 YFWSCHXAXPPKRF-SFTDATJTSA-N 0.000 claims 1
- WBNAUPFGRVUWEN-PMACEKPBSA-N (2s)-n-[6-[4-[2-[(2s)-pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]-1,2-benzoxazol-3-yl]pyrrolidine-2-carboxamide Chemical compound O=C([C@H]1NCCC1)NC(C1=CC=2)=NOC1=CC=2C(C=C1)=CC=C1C(N1)=CN=C1[C@@H]1CCCN1 WBNAUPFGRVUWEN-PMACEKPBSA-N 0.000 claims 1
- WGDXYMATFCDOFZ-PMACEKPBSA-N (2s)-n-[6-[4-[2-[(2s)-pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]-1h-indazol-3-yl]pyrrolidine-2-carboxamide Chemical compound O=C([C@H]1NCCC1)NC(C1=CC=2)=NNC1=CC=2C(C=C1)=CC=C1C(N1)=CN=C1[C@@H]1CCCN1 WGDXYMATFCDOFZ-PMACEKPBSA-N 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
- 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
- 108020005544 Antisense RNA Proteins 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 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
- 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
- 150000001721 carbon Chemical group 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
- 210000002443 helper t lymphocyte Anatomy 0.000 claims 1
- 125000004446 heteroarylalkyl group 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
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000006501 nitrophenyl group Chemical group 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 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
- 125000003003 spiro group Chemical group 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- OPANAHUKQCTHKE-SVBPBHIXSA-N tert-butyl (2s)-2-[5-[4-[3-[[(2s)-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carbonyl]amino]-1,2-benzoxazol-6-yl]phenyl]-1h-imidazol-2-yl]pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC[C@H]1C(=O)NC1=NOC2=CC(C=3C=CC(=CC=3)C=3NC(=NC=3)[C@H]3N(CCC3)C(=O)OC(C)(C)C)=CC=C12 OPANAHUKQCTHKE-SVBPBHIXSA-N 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
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US18216209P | 2009-05-29 | 2009-05-29 | |
| US61/182,162 | 2009-05-29 | ||
| PCT/US2010/036033 WO2010138488A1 (en) | 2009-05-29 | 2010-05-25 | Hepatitis c virus inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012528166A JP2012528166A (ja) | 2012-11-12 |
| JP2012528166A5 true JP2012528166A5 (OSRAM) | 2013-06-06 |
| JP5615352B2 JP5615352B2 (ja) | 2014-10-29 |
Family
ID=42990555
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012513170A Expired - Fee Related JP5615352B2 (ja) | 2009-05-29 | 2010-05-25 | Ｃ型肝炎ウイルス阻害剤 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US8211928B2 (OSRAM) |
| EP (1) | EP2435429B1 (OSRAM) |
| JP (1) | JP5615352B2 (OSRAM) |
| CN (1) | CN102459250B (OSRAM) |
| WO (1) | WO2010138488A1 (OSRAM) |
Families Citing this family (65)
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| JP2012513410A (ja) | 2008-12-23 | 2012-06-14 | アボット・ラボラトリーズ | 抗ウイルス化合物 |
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| US8188132B2 (en) | 2009-02-17 | 2012-05-29 | Enanta Pharmaceuticals, Inc. | Linked dibenzimidazole derivatives |
| US8394968B2 (en) | 2009-02-17 | 2013-03-12 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8101643B2 (en) | 2009-02-27 | 2012-01-24 | Enanta Pharmaceuticals, Inc. | Benzimidazole derivatives |
| US8673954B2 (en) | 2009-02-27 | 2014-03-18 | Enanta Pharmaceuticals, Inc. | Benzimidazole derivatives |
| US9765087B2 (en) | 2009-02-27 | 2017-09-19 | Enanta Pharmaceuticals, Inc. | Benzimidazole derivatives |
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-
2010
- 2010-05-24 US US12/785,665 patent/US8211928B2/en active Active
- 2010-05-25 JP JP2012513170A patent/JP5615352B2/ja not_active Expired - Fee Related
- 2010-05-25 CN CN201080034457.4A patent/CN102459250B/zh not_active Expired - Fee Related
- 2010-05-25 WO PCT/US2010/036033 patent/WO2010138488A1/en not_active Ceased
- 2010-05-25 EP EP10720511.4A patent/EP2435429B1/en not_active Not-in-force
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