CA2474031A1 - Tripeptides heterocycliques utiles en tant qu'inhibiteurs de l'hepatite c - Google Patents
Tripeptides heterocycliques utiles en tant qu'inhibiteurs de l'hepatite c Download PDFInfo
- Publication number
- CA2474031A1 CA2474031A1 CA002474031A CA2474031A CA2474031A1 CA 2474031 A1 CA2474031 A1 CA 2474031A1 CA 002474031 A CA002474031 A CA 002474031A CA 2474031 A CA2474031 A CA 2474031A CA 2474031 A1 CA2474031 A1 CA 2474031A1
- Authority
- CA
- Canada
- Prior art keywords
- formula
- compound
- butyl
- hydroxy
- cyclopentyl
- 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
- 239000003112 inhibitor Substances 0.000 title claims abstract 6
- 208000006454 hepatitis Diseases 0.000 title 1
- 231100000283 hepatitis Toxicity 0.000 title 1
- 125000000623 heterocyclic group Chemical group 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 22
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract 12
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract 9
- 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 abstract 6
- 150000003839 salts Chemical class 0.000 claims abstract 5
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract 4
- 239000003795 chemical substances by application Substances 0.000 claims 10
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 10
- 208000005176 Hepatitis C Diseases 0.000 claims 8
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 8
- 238000000034 method Methods 0.000 claims 7
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 241000124008 Mammalia Species 0.000 claims 5
- 108020004684 Internal Ribosome Entry Sites Proteins 0.000 claims 4
- 208000036142 Viral infection Diseases 0.000 claims 4
- 229940079322 interferon Drugs 0.000 claims 4
- 230000002265 prevention Effects 0.000 claims 4
- 230000009385 viral infection Effects 0.000 claims 4
- 108060004795 Methyltransferase Proteins 0.000 claims 2
- -1 O-(C1-6)alkyl Chemical group 0.000 claims 2
- 108091005804 Peptidases Proteins 0.000 claims 2
- 239000004365 Protease Substances 0.000 claims 2
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 claims 2
- 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 2
- 125000003368 amide group Chemical group 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 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
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 239000012752 auxiliary agent Substances 0.000 claims 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- HFFXLYHRNRKAPM-UHFFFAOYSA-N 2,4,5-trichloro-n-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide Chemical group O1C(C)=CC(NS(=O)(=O)C=2C(=CC(Cl)=C(Cl)C=2)Cl)=N1 HFFXLYHRNRKAPM-UHFFFAOYSA-N 0.000 abstract 1
- 101800001838 Serine protease/helicase NS3 Proteins 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
Classifications
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07K5/08—Tripeptides
- C07K5/0802—Tripeptides with the first amino acid being neutral
- C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
- C07K5/0808—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms, e.g. Val, Ile, Leu
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07K5/08—Tripeptides
- C07K5/0802—Tripeptides with the first amino acid being neutral
- C07K5/0812—Tripeptides with the first amino acid being neutral and aromatic or cycloaliphatic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07K5/08—Tripeptides
- C07K5/0827—Tripeptides containing heteroatoms different from O, S, or N
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
La présente invention concerne des composés représentés par la formule (I). Dans la formule, R?1¿ représente un dérivé hydroxyle ou sulfonamide; R?2¿ représente t-butyle ou CH¿2?-C(CH¿3?)¿3? ou CH¿2?-cyclopentyle; R¿3? représente t-butyle ou cyclohexyle et R?4¿ représente cyclobutyle, cyclopentyle ou cyclohexyle. Ces composés ou un sel pharmaceutiquement acceptable de ces derniers sont utiles en tant qu'inhibiteurs de la protéase de protéines non structurelles NS3 du virus de l'hépatite C (VHC). Formule (I)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA2474031A CA2474031C (fr) | 2002-02-01 | 2003-01-24 | Tripeptides heterocycliques utiles en tant qu'inhibiteurs de l'hepatite c |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA2,369,970 | 2002-02-01 | ||
| CA002369970A CA2369970A1 (fr) | 2002-02-01 | 2002-02-01 | Tri-peptides inhibiteur de l'hepatite c |
| PCT/CA2003/000091 WO2003064416A1 (fr) | 2002-02-01 | 2003-01-24 | Tripeptides heterocycliques utiles en tant qu'inhibiteurs de l'hepatite c |
| CA2474031A CA2474031C (fr) | 2002-02-01 | 2003-01-24 | Tripeptides heterocycliques utiles en tant qu'inhibiteurs de l'hepatite c |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2474031A1 true CA2474031A1 (fr) | 2003-08-07 |
| CA2474031C CA2474031C (fr) | 2010-08-24 |
Family
ID=32991606
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2474031A Expired - Fee Related CA2474031C (fr) | 2002-02-01 | 2003-01-24 | Tripeptides heterocycliques utiles en tant qu'inhibiteurs de l'hepatite c |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2474031C (fr) |
-
2003
- 2003-01-24 CA CA2474031A patent/CA2474031C/fr not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2474031C (fr) | 2010-08-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20150126 |