CA2869908C - Hepatitis c virus inhibitors - Google Patents
Hepatitis c virus inhibitors Download PDFInfo
- Publication number
- CA2869908C CA2869908C CA2869908A CA2869908A CA2869908C CA 2869908 C CA2869908 C CA 2869908C CA 2869908 A CA2869908 A CA 2869908A CA 2869908 A CA2869908 A CA 2869908A CA 2869908 C CA2869908 C CA 2869908C
- Authority
- CA
- Canada
- Prior art keywords
- compound
- 6alkyl
- mmol
- methyl
- 3alkyl
- 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.)
- Expired - Fee Related
Links
- 241000711549 Hepacivirus C Species 0.000 title claims abstract description 50
- 239000003112 inhibitor Substances 0.000 title claims abstract description 25
- 150000001875 compounds Chemical class 0.000 claims abstract description 200
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 40
- 150000003839 salts Chemical class 0.000 claims abstract description 33
- 208000005176 Hepatitis C Diseases 0.000 claims abstract description 17
- 208000036142 Viral infection Diseases 0.000 claims abstract description 16
- 230000010076 replication Effects 0.000 claims abstract description 16
- 230000009385 viral infection Effects 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 54
- 239000001257 hydrogen Substances 0.000 claims description 52
- -1 ̈SR e Chemical group 0.000 claims description 42
- 125000005843 halogen group Chemical group 0.000 claims description 36
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 34
- 150000002431 hydrogen Chemical group 0.000 claims description 28
- 241000124008 Mammalia Species 0.000 claims description 27
- 125000000623 heterocyclic group Chemical group 0.000 claims description 25
- 239000002777 nucleoside Substances 0.000 claims description 23
- 150000003833 nucleoside derivatives Chemical class 0.000 claims description 23
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 22
- 108010050904 Interferons Proteins 0.000 claims description 22
- 102000014150 Interferons Human genes 0.000 claims description 22
- 101800001014 Non-structural protein 5A Proteins 0.000 claims description 18
- 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 description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims description 17
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
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- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 230000002401 inhibitory effect Effects 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
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- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 15
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- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 230000017613 viral reproduction Effects 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
Classifications
-
- 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
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0816—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Virology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261637956P | 2012-04-25 | 2012-04-25 | |
| US61/637,956 | 2012-04-25 | ||
| US201361773977P | 2013-03-07 | 2013-03-07 | |
| US61/773,977 | 2013-03-07 | ||
| PCT/US2013/037934 WO2013163270A1 (en) | 2012-04-25 | 2013-04-24 | Hepatitis c virus inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2869908A1 CA2869908A1 (en) | 2013-10-31 |
| CA2869908C true CA2869908C (en) | 2018-02-20 |
Family
ID=48227586
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2869908A Expired - Fee Related CA2869908C (en) | 2012-04-25 | 2013-04-24 | Hepatitis c virus inhibitors |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US9066944B2 (enExample) |
| EP (1) | EP2850072B1 (enExample) |
| JP (1) | JP6069492B2 (enExample) |
| CN (1) | CN104302636B (enExample) |
| CA (1) | CA2869908C (enExample) |
| ES (1) | ES2599665T3 (enExample) |
| WO (1) | WO2013163270A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2624846T3 (es) * | 2012-04-25 | 2017-07-17 | Theravance Biopharma R&D Ip, Llc | Compuestos de piperazina-piperidina como inhibidores del virus de la hepatitis C |
| GB202013383D0 (en) * | 2020-08-26 | 2020-10-07 | Givaudan Sa | Process |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7659270B2 (en) | 2006-08-11 | 2010-02-09 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8329159B2 (en) | 2006-08-11 | 2012-12-11 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8303944B2 (en) | 2006-08-11 | 2012-11-06 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8147818B2 (en) | 2008-02-13 | 2012-04-03 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8729077B2 (en) | 2008-11-28 | 2014-05-20 | Glaxosmithkline Llc | Anti-viral compounds, compositions, and methods of use |
| WO2010094977A1 (en) * | 2009-02-23 | 2010-08-26 | Arrow Therapeutics Limited | Novel biphenyl compounds useful for the treatment of hepatitis c |
| WO2010096777A1 (en) | 2009-02-23 | 2010-08-26 | Presidio Pharmaceuticals, Inc. | Inhibitors of hcv ns5a |
| BRPI1010795B1 (pt) | 2009-05-13 | 2018-12-11 | Gilead Pharmasset Llc | compostos antivirais, seu uso e composição farmacêutica compreendendo os mesmos |
| US8822700B2 (en) | 2009-09-11 | 2014-09-02 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| US9156818B2 (en) | 2009-09-11 | 2015-10-13 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| US8377980B2 (en) | 2009-12-16 | 2013-02-19 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| PE20130244A1 (es) * | 2010-01-25 | 2013-03-10 | Enanta Pharm Inc | Inhibidores del virus de la hepatitis c |
| CN102918049A (zh) | 2010-03-09 | 2013-02-06 | 默沙东公司 | 稠合三环甲硅烷基化合物及其用于治疗病毒性疾病的方法 |
| EP2575819A4 (en) | 2010-06-04 | 2013-11-27 | Enanta Pharm Inc | INHIBITORS OF HEPATITIS C VIRUS |
| AU2010358561B2 (en) * | 2010-08-04 | 2016-06-02 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8697704B2 (en) * | 2010-08-12 | 2014-04-15 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| ES2548286T3 (es) * | 2010-11-04 | 2015-10-15 | Theravance Biopharma R&D Ip, Llc | Nuevos inhibidores del virus de la hepatitis C |
| CA2852700A1 (en) | 2011-11-03 | 2013-05-10 | Theravance, Inc. | Rod-like hepatitis c virus inhibitors containing the fragment {2-[4-(biphenyl-4-yl)-1h-imidazo-2-yl]pyrrolidine-1-carbonlymethyl}amine |
| US8883135B2 (en) * | 2012-05-03 | 2014-11-11 | Theravance Biopharma R&D Ip, Llc | Crystalline form of a pyridyl-piperazinyl hepatitis C virus inhibitor |
-
2013
- 2013-04-24 EP EP13719696.0A patent/EP2850072B1/en active Active
- 2013-04-24 CA CA2869908A patent/CA2869908C/en not_active Expired - Fee Related
- 2013-04-24 WO PCT/US2013/037934 patent/WO2013163270A1/en not_active Ceased
- 2013-04-24 ES ES13719696.0T patent/ES2599665T3/es active Active
- 2013-04-24 CN CN201380022245.8A patent/CN104302636B/zh not_active Expired - Fee Related
- 2013-04-24 US US13/869,228 patent/US9066944B2/en not_active Expired - Fee Related
- 2013-04-24 JP JP2015509101A patent/JP6069492B2/ja not_active Expired - Fee Related
-
2015
- 2015-05-21 US US14/718,296 patent/US9365549B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN104302636B (zh) | 2017-03-29 |
| US20130287731A1 (en) | 2013-10-31 |
| CN104302636A (zh) | 2015-01-21 |
| US9365549B2 (en) | 2016-06-14 |
| JP2015515494A (ja) | 2015-05-28 |
| EP2850072A1 (en) | 2015-03-25 |
| JP6069492B2 (ja) | 2017-02-01 |
| US9066944B2 (en) | 2015-06-30 |
| EP2850072B1 (en) | 2016-08-31 |
| US20150252023A1 (en) | 2015-09-10 |
| CA2869908A1 (en) | 2013-10-31 |
| WO2013163270A1 (en) | 2013-10-31 |
| ES2599665T3 (es) | 2017-02-02 |
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| CA2869908C (en) | Hepatitis c virus inhibitors | |
| CA2869640C (en) | Piperazine-piperidine compounds as hepatitis c virus inhibitors | |
| NZ623846B2 (en) | Rod-like hepatitis c virus inhibitors containing the fragment {2-[4-(bi phenyl-4-yl) -1h-imidazo-2-yl] pyrrolidine-1-carbonlymethyl} amine |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20160426 |
|
| MKLA | Lapsed |
Effective date: 20190424 |