MX2012000695A - Análogos de bencimidazol para el tratamiento o la prevención de infecciones por flavivirus. - Google Patents
Análogos de bencimidazol para el tratamiento o la prevención de infecciones por flavivirus.Info
- Publication number
- MX2012000695A MX2012000695A MX2012000695A MX2012000695A MX2012000695A MX 2012000695 A MX2012000695 A MX 2012000695A MX 2012000695 A MX2012000695 A MX 2012000695A MX 2012000695 A MX2012000695 A MX 2012000695A MX 2012000695 A MX2012000695 A MX 2012000695A
- Authority
- MX
- Mexico
- Prior art keywords
- nrarb
- substituted
- unsubstituted
- independently
- ora
- Prior art date
Links
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title claims description 7
- 230000002265 prevention Effects 0.000 title description 5
- 206010054261 Flavivirus infection Diseases 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 476
- 150000003839 salts Chemical class 0.000 claims abstract description 59
- 229910052796 boron Inorganic materials 0.000 claims abstract description 31
- 208000036142 Viral infection Diseases 0.000 claims abstract description 22
- 230000009385 viral infection Effects 0.000 claims abstract description 21
- 229910003827 NRaRb Inorganic materials 0.000 claims description 851
- 125000000217 alkyl group Chemical group 0.000 claims description 481
- 125000000623 heterocyclic group Chemical group 0.000 claims description 394
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 294
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 267
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 258
- 125000003342 alkenyl group Chemical group 0.000 claims description 257
- 125000001072 heteroaryl group Chemical group 0.000 claims description 247
- 229910052736 halogen Inorganic materials 0.000 claims description 239
- 125000000304 alkynyl group Chemical group 0.000 claims description 226
- -1 -ORa Chemical group 0.000 claims description 220
- 125000003118 aryl group Chemical group 0.000 claims description 212
- 150000002367 halogens Chemical class 0.000 claims description 211
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 205
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 169
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 156
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 147
- MPVDXIMFBOLMNW-UHFFFAOYSA-N chembl1615565 Chemical compound OC1=CC=C2C=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=C1N=NC1=CC=CC=C1 MPVDXIMFBOLMNW-UHFFFAOYSA-N 0.000 claims description 125
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 118
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 117
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 115
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 115
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 87
- 229910052799 carbon Inorganic materials 0.000 claims description 86
- 125000004429 atom Chemical group 0.000 claims description 80
- 239000003795 chemical substances by application Substances 0.000 claims description 80
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 80
- 229910052739 hydrogen Inorganic materials 0.000 claims description 67
- 239000003112 inhibitor Substances 0.000 claims description 66
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 62
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 55
- 230000003612 virological effect Effects 0.000 claims description 49
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 45
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 claims description 45
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 43
- 125000003545 alkoxy group Chemical group 0.000 claims description 41
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 38
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 34
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 32
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 29
- 125000005843 halogen group Chemical group 0.000 claims description 28
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 27
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 24
- 229910052702 rhenium Inorganic materials 0.000 claims description 24
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 23
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 23
- 239000003814 drug Substances 0.000 claims description 23
- 125000001153 fluoro group Chemical group F* 0.000 claims description 23
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 21
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- 239000008194 pharmaceutical composition Substances 0.000 claims description 20
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 18
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 18
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- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical group 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 description 13
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- 125000002541 furyl group Chemical group 0.000 claims description 13
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- 229960000329 ribavirin Drugs 0.000 claims description 13
- 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 description 13
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 13
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- 230000000692 anti-sense effect Effects 0.000 claims description 12
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 12
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- 125000002883 imidazolyl group Chemical group 0.000 claims description 12
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- 125000003373 pyrazinyl group Chemical group 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 12
- 125000001425 triazolyl group Chemical group 0.000 claims description 12
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 11
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- 125000005874 benzothiadiazolyl group Chemical group 0.000 claims description 11
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- 125000005433 dihydrobenzodioxinyl group Chemical group O1C(COC2=C1C=CC=C2)* 0.000 claims description 11
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- 239000000546 pharmaceutical excipient Substances 0.000 claims description 11
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 11
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 11
- 125000004587 thienothienyl group Chemical group S1C(=CC2=C1C=CS2)* 0.000 claims description 11
- 208000005176 Hepatitis C Diseases 0.000 claims description 10
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 9
- 229910052705 radium Inorganic materials 0.000 claims description 9
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 9
- 125000001041 indolyl group Chemical group 0.000 claims description 8
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 7
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 7
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- 125000003072 pyrazolidinyl group Chemical group 0.000 claims description 7
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- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 6
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- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 4
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- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims 2
- OXOBKZZXZVFOBB-INIZCTEOSA-N (2s)-2-benzhydrylpyrrolidine Chemical compound C1CCN[C@@H]1C(C=1C=CC=CC=1)C1=CC=CC=C1 OXOBKZZXZVFOBB-INIZCTEOSA-N 0.000 claims 1
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Classifications
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- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06034—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms
- C07K5/06052—Val-amino acid
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- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
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- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Hematology (AREA)
- Obesity (AREA)
- Communicable Diseases (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
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| PCT/US2010/042340 WO2011009084A2 (en) | 2009-07-16 | 2010-07-16 | Benzimidazole analogues for the treatment or prevention of flavivirus infections |
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| WO2010075376A2 (en) | 2008-12-23 | 2010-07-01 | Abbott Laboratories | Anti-viral compounds |
| US8314135B2 (en) | 2009-02-09 | 2012-11-20 | Enanta Pharmaceuticals, Inc. | Linked dibenzimidazole antivirals |
| US8242156B2 (en) | 2009-02-17 | 2012-08-14 | Enanta Pharmaceuticals, Inc. | Linked dibenzimidazole derivatives |
| US8394968B2 (en) | 2009-02-17 | 2013-03-12 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8188132B2 (en) | 2009-02-17 | 2012-05-29 | Enanta Pharmaceuticals, Inc. | Linked dibenzimidazole derivatives |
| US9765087B2 (en) | 2009-02-27 | 2017-09-19 | Enanta Pharmaceuticals, Inc. | Benzimidazole derivatives |
| US8673954B2 (en) | 2009-02-27 | 2014-03-18 | Enanta Pharmaceuticals, Inc. | Benzimidazole derivatives |
| US8101643B2 (en) | 2009-02-27 | 2012-01-24 | Enanta Pharmaceuticals, Inc. | Benzimidazole derivatives |
| US8796466B2 (en) | 2009-03-30 | 2014-08-05 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| TW201038559A (en) | 2009-04-09 | 2010-11-01 | Bristol Myers Squibb Co | Hepatitis C virus inhibitors |
| US8143414B2 (en) | 2009-04-13 | 2012-03-27 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| EP2419404B1 (en) | 2009-04-15 | 2015-11-04 | AbbVie Inc. | Anti-viral compounds |
| RS56654B8 (sr) | 2009-05-13 | 2021-06-30 | Gilead Pharmasset Llc | Antiviralna jedinjenja |
| US8211928B2 (en) | 2009-05-29 | 2012-07-03 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8772505B2 (en) * | 2009-05-29 | 2014-07-08 | Merck Sharp & Dohme Corp. | Antiviral compounds composed of three aligned aryl moieties to treat diseases such as hepatitis C |
| US8138215B2 (en) | 2009-05-29 | 2012-03-20 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8937150B2 (en) | 2009-06-11 | 2015-01-20 | Abbvie Inc. | Anti-viral compounds |
| US9394279B2 (en) | 2009-06-11 | 2016-07-19 | Abbvie Inc. | Anti-viral compounds |
| US8716454B2 (en) | 2009-06-11 | 2014-05-06 | Abbvie Inc. | Solid compositions |
| EA020031B1 (ru) | 2009-06-11 | 2014-08-29 | Эббви Бахамаз Лтд. | Противовирусные соединения |
| US8221737B2 (en) | 2009-06-16 | 2012-07-17 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| EP2454254A2 (en) * | 2009-07-16 | 2012-05-23 | Vertex Pharmaceuticals Incorporated | Benzimidazole analogues for the treatment or prevention of flavivirus infections |
| RU2012112824A (ru) * | 2009-09-03 | 2013-10-10 | Тиботек Фармасьютикалз | Производные бис-бензимидазола |
| EP2473056A4 (en) | 2009-09-04 | 2013-02-13 | Glaxosmithkline Llc | CHEMICAL COMPOUNDS |
| US8759332B2 (en) | 2009-09-11 | 2014-06-24 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| US9156818B2 (en) | 2009-09-11 | 2015-10-13 | 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 |
| SG181797A1 (en) * | 2009-12-18 | 2012-07-30 | Idenix Pharmaceuticals Inc | 5,5-fused arylene or heteroarylene hepatitis c virus inhibitors |
| US8362020B2 (en) | 2009-12-30 | 2013-01-29 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8933110B2 (en) | 2010-01-25 | 2015-01-13 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| CN102843909A (zh) | 2010-01-25 | 2012-12-26 | 埃南塔制药公司 | 丙型肝炎病毒抑制剂 |
| US8178531B2 (en) | 2010-02-23 | 2012-05-15 | Enanta Pharmaceuticals, Inc. | Antiviral agents |
| US8623814B2 (en) | 2010-02-23 | 2014-01-07 | 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 |
| MX2012010918A (es) | 2010-03-24 | 2013-01-18 | Vertex Pharma | Analogos para el tratamiento o prevencion de infecciones por flavivirus. |
| TW201139438A (en) * | 2010-03-24 | 2011-11-16 | Vertex Pharma | Analogues for the treatment or prevention of flavivirus infections |
| WO2011127350A1 (en) | 2010-04-09 | 2011-10-13 | Enanta Pharmaceuticals, Inc. | Hepatitis c virus inhibitors |
| US8778938B2 (en) | 2010-06-04 | 2014-07-15 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| NZ605440A (en) | 2010-06-10 | 2014-05-30 | Abbvie Bahamas Ltd | Solid compositions comprising an hcv inhibitor |
| EP2603080A4 (en) | 2010-08-12 | 2014-01-22 | Enanta Pharm Inc | HEPATITIS C-VIRUS HEMMER |
| US20150158909A1 (en) * | 2010-12-15 | 2015-06-11 | Abbevie Inc. | Anti-viral compounds |
| MX2013006828A (es) * | 2010-12-16 | 2014-10-14 | Abbvie Inc | Compuestos antivirales. |
| WO2012087976A2 (en) * | 2010-12-21 | 2012-06-28 | Intermune, Inc. | Novel inhibitors of hepatitis c virus replication |
| US8552047B2 (en) | 2011-02-07 | 2013-10-08 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
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| WO2011009084A3 (en) | 2011-04-28 |
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