EA022384B1 - Ингибиторы вируса гепатита c - Google Patents
Ингибиторы вируса гепатита c Download PDFInfo
- Publication number
- EA022384B1 EA022384B1 EA201171152A EA201171152A EA022384B1 EA 022384 B1 EA022384 B1 EA 022384B1 EA 201171152 A EA201171152 A EA 201171152A EA 201171152 A EA201171152 A EA 201171152A EA 022384 B1 EA022384 B1 EA 022384B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- phenyl
- imidazol
- pyrrolidinyl
- alkyl
- hydrogen
- Prior art date
Links
- 241000711549 Hepacivirus C Species 0.000 title abstract description 59
- 239000003112 inhibitor Substances 0.000 title description 43
- 150000001875 compounds Chemical class 0.000 claims abstract description 169
- 238000000034 method Methods 0.000 claims abstract description 76
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 155
- -1 (methoxycarbonyl) amino Chemical group 0.000 claims description 146
- 239000001257 hydrogen Substances 0.000 claims description 108
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 102
- 150000003839 salts Chemical class 0.000 claims description 84
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 69
- 125000003118 aryl group Chemical group 0.000 claims description 68
- 125000000217 alkyl group Chemical group 0.000 claims description 64
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 59
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 46
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 44
- 239000000460 chlorine Chemical group 0.000 claims description 41
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 38
- 239000000126 substance Substances 0.000 claims description 36
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 34
- 125000004432 carbon atom Chemical group C* 0.000 claims description 30
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 27
- 239000004202 carbamide Substances 0.000 claims description 21
- 125000002619 bicyclic group Chemical group 0.000 claims description 20
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- 108090000623 proteins and genes Proteins 0.000 claims description 18
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- 102000004169 proteins and genes Human genes 0.000 claims description 17
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 15
- 125000003367 polycyclic group Chemical group 0.000 claims description 15
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 229910052700 potassium Inorganic materials 0.000 claims description 14
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- 125000005842 heteroatom Chemical group 0.000 claims description 13
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- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
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- 125000001475 halogen functional group Chemical group 0.000 claims description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
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Classifications
-
- 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
- C07D403/02—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 two hetero rings
- C07D403/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4178—1,3-Diazoles not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Virology (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Communicable Diseases (AREA)
- Molecular Biology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
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| US16453109P | 2009-03-30 | 2009-03-30 | |
| US12/729,940 US8796466B2 (en) | 2009-03-30 | 2010-03-23 | Hepatitis C virus inhibitors |
| PCT/US2010/028456 WO2010117635A1 (en) | 2009-03-30 | 2010-03-24 | Hepatitis c virus inhibitors |
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| EA201171152A1 EA201171152A1 (ru) | 2012-10-30 |
| EA022384B1 true EA022384B1 (ru) | 2015-12-30 |
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| EA201171152A EA022384B1 (ru) | 2009-03-30 | 2010-03-24 | Ингибиторы вируса гепатита c |
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| AU (1) | AU2010234970A1 (enExample) |
| BR (1) | BRPI1013393A2 (enExample) |
| CA (1) | CA2757269A1 (enExample) |
| CL (1) | CL2011002426A1 (enExample) |
| CO (1) | CO6430431A2 (enExample) |
| EA (1) | EA022384B1 (enExample) |
| IL (1) | IL215055A0 (enExample) |
| MX (1) | MX2011009948A (enExample) |
| NZ (1) | NZ595168A (enExample) |
| PE (1) | PE20120546A1 (enExample) |
| SG (1) | SG174521A1 (enExample) |
| WO (1) | WO2010117635A1 (enExample) |
| ZA (1) | ZA201106795B (enExample) |
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| RU2505539C2 (ru) | 2008-12-23 | 2014-01-27 | Эбботт Лэборетриз | Антивирусные соединения |
| US8541424B2 (en) * | 2008-12-23 | 2013-09-24 | 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 |
| 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 |
| 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 |
| 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 |
| JP5734956B2 (ja) * | 2009-04-15 | 2015-06-17 | アッヴィ・インコーポレイテッド | 抗ウィルス化合物 |
| JP2012524761A (ja) * | 2009-04-24 | 2012-10-18 | テイボテク・フアーマシユーチカルズ | ジアリールエーテル類 |
| NZ619205A (en) | 2009-05-13 | 2015-04-24 | Gilead Pharmasset Llc | Antiviral compounds |
| 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 |
| US8937150B2 (en) | 2009-06-11 | 2015-01-20 | Abbvie Inc. | Anti-viral compounds |
| US8716454B2 (en) | 2009-06-11 | 2014-05-06 | Abbvie Inc. | Solid compositions |
| PL2368890T3 (pl) * | 2009-06-11 | 2013-10-31 | Abbvie Bahamas Ltd | Inhibitory wirusa zapalenia wątroby C |
| US9394279B2 (en) | 2009-06-11 | 2016-07-19 | Abbvie Inc. | Anti-viral compounds |
| US8221737B2 (en) | 2009-06-16 | 2012-07-17 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| US8609648B2 (en) | 2009-07-02 | 2013-12-17 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| JP2012533569A (ja) | 2009-07-16 | 2012-12-27 | ヴァーテックス ファーマシューティカルズ、 インコーポレイテッド | フラビウイルス感染症を治療又は予防するためのベンゾイミダゾール類似体 |
| NZ597982A (en) | 2009-09-04 | 2013-01-25 | Glaxosmithkline Llc | CHEMICAL COMPOUNDS for treating Hepatitis C virus |
| US8815928B2 (en) | 2009-09-11 | 2014-08-26 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| US8822700B2 (en) | 2009-09-11 | 2014-09-02 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| US8927709B2 (en) | 2009-09-11 | 2015-01-06 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| WO2011031904A1 (en) | 2009-09-11 | 2011-03-17 | Enanta Pharmaceuticals, Inc | Hepatitis c virus inhibitors |
| US8759332B2 (en) | 2009-09-11 | 2014-06-24 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| US8703938B2 (en) | 2009-09-11 | 2014-04-22 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| US20110274648A1 (en) | 2009-11-11 | 2011-11-10 | Bristol-Myers Squibb Company | Hepatitis C Virus Inhibitors |
| US20110269956A1 (en) | 2009-11-11 | 2011-11-03 | Bristol-Myers Squibb Company | Hepatitis C Virus Inhibitors |
| US20110281910A1 (en) | 2009-11-12 | 2011-11-17 | Bristol-Myers Squibb Company | Hepatitis C Virus Inhibitors |
| EP2512480A4 (en) * | 2009-12-14 | 2013-05-15 | Enanta Pharm Inc | HEPATITIS C-VIRUS HEMMER |
| US8377980B2 (en) | 2009-12-16 | 2013-02-19 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
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| MX2012008658A (es) | 2010-01-25 | 2012-12-05 | Enanta Pharm Inc | Inhibidores del virus de la hepatitis c. |
| US8933110B2 (en) | 2010-01-25 | 2015-01-13 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| 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 |
| BR112012022311A2 (pt) | 2010-03-04 | 2016-08-23 | Enanta Pharm Inc | agentes farmacêuticos de combinação como inibidores da replicação de hcv. |
| JP2013522375A (ja) * | 2010-03-24 | 2013-06-13 | バーテックス ファーマシューティカルズ インコーポレイテッド | フラビウイルス感染を処置または予防するためのアナログ |
| US9127021B2 (en) | 2010-04-09 | 2015-09-08 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| EP2575475A4 (en) * | 2010-05-28 | 2013-11-27 | Presidio Pharmaceuticals Inc | HCV NS5A 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 |
| AU2011276526A1 (en) | 2010-06-28 | 2013-01-10 | Vertex Pharmaceuticals Incorporated | Compounds and methods for the treatment or prevention of Flavivirus infections |
| WO2012006060A1 (en) | 2010-06-28 | 2012-01-12 | Vertex Pharmaceuticals Incorporated | Compounds and methods for the treatment or prevention of flavivirus infections |
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| MX2011009948A (es) | 2011-10-06 |
| AR076002A1 (es) | 2011-05-11 |
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