JP2012522053A5 - - Google Patents
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- Publication number
- JP2012522053A5 JP2012522053A5 JP2012503512A JP2012503512A JP2012522053A5 JP 2012522053 A5 JP2012522053 A5 JP 2012522053A5 JP 2012503512 A JP2012503512 A JP 2012503512A JP 2012503512 A JP2012503512 A JP 2012503512A JP 2012522053 A5 JP2012522053 A5 JP 2012522053A5
- Authority
- JP
- Japan
- Prior art keywords
- imidazol
- phenyl
- pyrrolidinyl
- methyl
- alkyl
- 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 carboxy, formyl Chemical group 0.000 claims 89
- 229910052739 hydrogen Inorganic materials 0.000 claims 56
- 239000001257 hydrogen Substances 0.000 claims 56
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 46
- 125000000217 alkyl group Chemical group 0.000 claims 45
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 36
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 33
- 150000002431 hydrogen Chemical group 0.000 claims 30
- 150000001875 compounds Chemical class 0.000 claims 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 25
- 125000003118 aryl group Chemical group 0.000 claims 24
- 125000000753 cycloalkyl group Chemical group 0.000 claims 21
- 125000003710 aryl alkyl group Chemical group 0.000 claims 20
- 150000003839 salts Chemical class 0.000 claims 20
- 229910052736 halogen Inorganic materials 0.000 claims 16
- 150000002367 halogens Chemical class 0.000 claims 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 16
- 125000000623 heterocyclic group Chemical group 0.000 claims 15
- 229910052757 nitrogen Inorganic materials 0.000 claims 15
- 229910052799 carbon Inorganic materials 0.000 claims 14
- 125000004432 carbon atom Chemical group C* 0.000 claims 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 14
- 125000001424 substituent group Chemical group 0.000 claims 14
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 13
- 125000001072 heteroaryl group Chemical group 0.000 claims 12
- 125000001188 haloalkyl group Chemical group 0.000 claims 8
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 7
- 239000004202 carbamide Substances 0.000 claims 7
- 125000005843 halogen group Chemical group 0.000 claims 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 4
- 125000002619 bicyclic group Chemical group 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 239000001301 oxygen Chemical group 0.000 claims 4
- 229910052717 sulfur Chemical group 0.000 claims 4
- 239000011593 sulfur 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
- 125000005469 ethylenyl group Chemical group 0.000 claims 3
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 3
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 3
- 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
- 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
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000004390 alkyl sulfonyl 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
- 125000004391 aryl sulfonyl 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
- 239000003184 complementary RNA Substances 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims 2
- 210000002443 helper t lymphocyte Anatomy 0.000 claims 2
- 125000002768 hydroxyalkyl 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
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 125000004430 oxygen atom 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
- 125000003003 spiro group Chemical group 0.000 claims 2
- ZBGKKYUXZMMPHM-JPYDVTDNSA-N (2r)-2-hydroxy-1-[(2s)-2-[5-[4-[2-[4-[2-[(2s)-1-[(2r)-2-hydroxy-2-phenylacetyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]ethyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-phenylethanone Chemical compound C1([C@@H](O)C(=O)N2CCC[C@H]2C=2NC=C(N=2)C2=CC=C(C=C2)CCC2=CC=C(C=C2)C=2N=C(NC=2)[C@@H]2CCCN2C(=O)[C@H](O)C=2C=CC=CC=2)=CC=CC=C1 ZBGKKYUXZMMPHM-JPYDVTDNSA-N 0.000 claims 1
- YLKPEGAEKOBUPL-JPYDVTDNSA-N (2r)-2-hydroxy-1-[(2s)-2-[5-[4-[[3-[2-[(2s)-1-[(2r)-2-hydroxy-2-phenylacetyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]methoxymethyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-phenylethanone Chemical compound C1([C@@H](O)C(=O)N2CCC[C@H]2C=2NC=C(N=2)C=2C=CC=C(C=2)COCC2=CC=C(C=C2)C=2N=C(NC=2)[C@@H]2CCCN2C(=O)[C@H](O)C=2C=CC=CC=2)=CC=CC=C1 YLKPEGAEKOBUPL-JPYDVTDNSA-N 0.000 claims 1
- URBNHSPLMPSGPV-IYTFMMMVSA-N 1-ethyl-3-[(1R)-2-[(2S)-2-[5-[4-[2-[4-[2-[(2S)-1-[(2R)-2-(ethylcarbamoylamino)-2-phenylacetyl]pyrrolidin-2-yl]-1H-imidazol-5-yl]phenyl]ethyl]phenyl]-1H-imidazol-2-yl]pyrrolidin-1-yl]-2-oxo-1-phenylethyl]urea Chemical compound C1([C@@H](NC(=O)NCC)C(=O)N2CCC[C@H]2C=2NC=C(N=2)C2=CC=C(C=C2)CCC2=CC=C(C=C2)C=2N=C(NC=2)[C@@H]2CCCN2C(=O)[C@H](NC(=O)NCC)C=2C=CC=CC=2)=CC=CC=C1 URBNHSPLMPSGPV-IYTFMMMVSA-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
- 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
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 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
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
- 125000006501 nitrophenyl group Chemical group 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16453109P | 2009-03-30 | 2009-03-30 | |
| US61/164,531 | 2009-03-30 | ||
| US12/729,940 US8796466B2 (en) | 2009-03-30 | 2010-03-23 | Hepatitis C virus inhibitors |
| US12/729,940 | 2010-03-23 | ||
| PCT/US2010/028456 WO2010117635A1 (en) | 2009-03-30 | 2010-03-24 | Hepatitis c virus inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012522053A JP2012522053A (ja) | 2012-09-20 |
| JP2012522053A5 true JP2012522053A5 (https=) | 2013-04-25 |
| JP5612660B2 JP5612660B2 (ja) | 2014-10-22 |
Family
ID=42320079
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012503512A Expired - Fee Related JP5612660B2 (ja) | 2009-03-30 | 2010-03-24 | Ｃ型肝炎ウイルス阻害剤 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US8796466B2 (https=) |
| EP (1) | EP2414350B1 (https=) |
| JP (1) | JP5612660B2 (https=) |
| KR (1) | KR20120034603A (https=) |
| CN (1) | CN102448956B (https=) |
| AR (1) | AR076002A1 (https=) |
| AU (1) | AU2010234970A1 (https=) |
| BR (1) | BRPI1013393A2 (https=) |
| CA (1) | CA2757269A1 (https=) |
| CL (1) | CL2011002426A1 (https=) |
| CO (1) | CO6430431A2 (https=) |
| EA (1) | EA022384B1 (https=) |
| IL (1) | IL215055A0 (https=) |
| MX (1) | MX2011009948A (https=) |
| NZ (1) | NZ595168A (https=) |
| PE (1) | PE20120546A1 (https=) |
| SG (1) | SG174521A1 (https=) |
| WO (1) | WO2010117635A1 (https=) |
| ZA (1) | ZA201106795B (https=) |
Families Citing this family (91)
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|---|---|---|---|---|
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| US9765087B2 (en) | 2009-02-27 | 2017-09-19 | Enanta Pharmaceuticals, Inc. | Benzimidazole derivatives |
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| TW201038559A (en) | 2009-04-09 | 2010-11-01 | Bristol Myers Squibb Co | Hepatitis C virus inhibitors |
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| US8138215B2 (en) | 2009-05-29 | 2012-03-20 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
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| CN102480971B (zh) | 2009-09-04 | 2014-11-26 | 杨森制药公司 | 化合物 |
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| US8759332B2 (en) | 2009-09-11 | 2014-06-24 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| US20110269956A1 (en) | 2009-11-11 | 2011-11-03 | Bristol-Myers Squibb Company | Hepatitis C Virus Inhibitors |
| US20110274648A1 (en) | 2009-11-11 | 2011-11-10 | Bristol-Myers Squibb Company | Hepatitis C Virus Inhibitors |
| US20110281910A1 (en) | 2009-11-12 | 2011-11-17 | Bristol-Myers Squibb Company | Hepatitis C Virus Inhibitors |
| US8653070B2 (en) | 2009-12-14 | 2014-02-18 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| US8377980B2 (en) | 2009-12-16 | 2013-02-19 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8362020B2 (en) | 2009-12-30 | 2013-01-29 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
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| US8933110B2 (en) | 2010-01-25 | 2015-01-13 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| US8623814B2 (en) | 2010-02-23 | 2014-01-07 | Enanta Pharmaceuticals, Inc. | Antiviral agents |
| US8178531B2 (en) | 2010-02-23 | 2012-05-15 | Enanta Pharmaceuticals, Inc. | Antiviral agents |
| CN102858157A (zh) | 2010-03-04 | 2013-01-02 | 埃南塔制药公司 | 作为hcv复制的抑制剂的组合药物活性剂 |
| CN102869657A (zh) | 2010-03-24 | 2013-01-09 | 沃泰克斯药物股份有限公司 | 用于治疗或预防黄病毒感染的类似物 |
| EP2555622A4 (en) | 2010-04-09 | 2013-09-18 | Enanta Pharm Inc | HEPATITIS C-VIRUS HEMMER |
| US20130296311A1 (en) * | 2010-05-28 | 2013-11-07 | Presidio Pharmaceuticals, Inc. | Inhibitors of hcv ns5a |
| US8778938B2 (en) | 2010-06-04 | 2014-07-15 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
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| JP5906253B2 (ja) * | 2010-12-16 | 2016-04-20 | アッヴィ・インコーポレイテッド | 抗ウイルス性化合物 |
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| AU2012286853A1 (en) | 2011-07-26 | 2013-05-02 | Vertex Pharmaceuticals Incorporated | Thiophene compounds |
| WO2013016499A1 (en) | 2011-07-26 | 2013-01-31 | Vertex Pharmaceuticals Incorporated | Methods for preparation of thiophene compounds |
| WO2013021344A1 (en) | 2011-08-08 | 2013-02-14 | Lupin Limited | Imidazole derivatives as antiviral agents |
| EP2709613B2 (en) | 2011-09-16 | 2020-08-12 | Gilead Pharmasset LLC | Methods for treating hcv |
| SG11201401891RA (en) | 2011-11-03 | 2014-05-29 | Theravance Inc | Rod -like hepatitis c virus inhibitors containing the fragement {2- [4- (bi phenyl - 4 - yl) - 1h - imidazo - 2 - yl] pyrrolidine - 1 - carbonlymethyl} amine |
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| US9034832B2 (en) | 2011-12-29 | 2015-05-19 | Abbvie Inc. | Solid compositions |
| US9326973B2 (en) | 2012-01-13 | 2016-05-03 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| WO2013142157A1 (en) | 2012-03-22 | 2013-09-26 | Alios Biopharma, Inc. | Pharmaceutical combinations comprising a thionucleotide analog |
| WO2013163262A1 (en) | 2012-04-25 | 2013-10-31 | Theravance, Inc. | Piperazine-piperidine compounds as hepatitis c virus inhibitors |
| EP2950786B1 (en) | 2013-01-31 | 2019-11-27 | Gilead Pharmasset LLC | Combination formulation of two antiviral compounds |
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