JP4914354B2 - Ｃ型肝炎インヒビターペプチド類似体 - Google Patents
Ｃ型肝炎インヒビターペプチド類似体 Download PDFInfo
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- JP4914354B2 JP4914354B2 JP2007521757A JP2007521757A JP4914354B2 JP 4914354 B2 JP4914354 B2 JP 4914354B2 JP 2007521757 A JP2007521757 A JP 2007521757A JP 2007521757 A JP2007521757 A JP 2007521757A JP 4914354 B2 JP4914354 B2 JP 4914354B2
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- 108090000765 processed proteins & peptides Proteins 0.000 title claims description 12
- 239000003112 inhibitor Substances 0.000 title description 48
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- 125000000217 alkyl group Chemical group 0.000 claims description 384
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- 125000001424 substituent group Chemical group 0.000 claims description 109
- 125000003118 aryl group Chemical group 0.000 claims description 98
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 67
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 62
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 56
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 56
- 229910052736 halogen Inorganic materials 0.000 claims description 55
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 44
- 150000003839 salts Chemical class 0.000 claims description 42
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 40
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 32
- 229910052717 sulfur Inorganic materials 0.000 claims description 30
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 29
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- 125000005842 heteroatom Chemical group 0.000 claims description 27
- 229910052757 nitrogen Inorganic materials 0.000 claims description 26
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- 125000005843 halogen group Chemical group 0.000 claims description 22
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
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- FNXKBSAUKFCXIK-UHFFFAOYSA-M sodium;hydrogen carbonate;8-hydroxy-7-iodoquinoline-5-sulfonic acid Chemical class [Na+].OC([O-])=O.C1=CN=C2C(O)=C(I)C=C(S(O)(=O)=O)C2=C1 FNXKBSAUKFCXIK-UHFFFAOYSA-M 0.000 description 1
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- 238000001228 spectrum Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
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- 238000007920 subcutaneous administration Methods 0.000 description 1
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- NHKZSTHOYNWEEZ-AFCXAGJDSA-N taribavirin Chemical compound N1=C(C(=N)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 NHKZSTHOYNWEEZ-AFCXAGJDSA-N 0.000 description 1
- 229950006081 taribavirin Drugs 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
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- IQFYYKKMVGJFEH-CSMHCCOUSA-N telbivudine Chemical compound O=C1NC(=O)C(C)=CN1[C@H]1O[C@@H](CO)[C@H](O)C1 IQFYYKKMVGJFEH-CSMHCCOUSA-N 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CMARJZRIECEQDX-UHFFFAOYSA-N tert-butyl (2-methylpropan-2-yl)oxycarbonyl carbonate;carboxy hydrogen carbonate Chemical compound OC(=O)OC(O)=O.CC(C)(C)OC(=O)OC(=O)OC(C)(C)C CMARJZRIECEQDX-UHFFFAOYSA-N 0.000 description 1
- PYJBLCPUFFGGKV-UHFFFAOYSA-N tert-butyl 1-sulfamoylcyclopropane-1-carboxylate Chemical compound CC(C)(C)OC(=O)C1(S(N)(=O)=O)CC1 PYJBLCPUFFGGKV-UHFFFAOYSA-N 0.000 description 1
- SOROHDKXLRHTPF-UHFFFAOYSA-N tert-butyl 2-methyl-2-sulfamoylcyclopropane-1-carboxylate Chemical compound CC(C)(C)OC(=O)C1CC1(C)S(N)(=O)=O SOROHDKXLRHTPF-UHFFFAOYSA-N 0.000 description 1
- NBXGDPBFRRQZEV-UHFFFAOYSA-N tert-butyl n-cyclopropylsulfonylcarbamate Chemical compound CC(C)(C)OC(=O)NS(=O)(=O)C1CC1 NBXGDPBFRRQZEV-UHFFFAOYSA-N 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical class CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- 229960004559 theobromine Drugs 0.000 description 1
- XJRBFBKDHIEHJR-UHFFFAOYSA-N thieno[3,2-b]pyridin-2-ol Chemical compound C1=CC=C2SC(O)=CC2=N1 XJRBFBKDHIEHJR-UHFFFAOYSA-N 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- DKGYESBFCGKOJC-UHFFFAOYSA-N thiophen-3-amine Chemical compound NC=1C=CSC=1 DKGYESBFCGKOJC-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 206010043778 thyroiditis Diseases 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
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- 238000001665 trituration Methods 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
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- 239000012588 trypsin Substances 0.000 description 1
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- 201000001862 viral hepatitis Diseases 0.000 description 1
- 230000008299 viral mechanism Effects 0.000 description 1
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Classifications
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- 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
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
-
- 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
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- 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
- 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
- C07K5/06139—Dipeptides with the first amino acid being heterocyclic
-
- 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
- C07K5/06—Dipeptides
- C07K5/06191—Dipeptides 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)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Public Health (AREA)
- Biochemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Veterinary Medicine (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Virology (AREA)
- Oncology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Communicable Diseases (AREA)
- Gastroenterology & Hepatology (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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US58943504P | 2004-07-20 | 2004-07-20 | |
| US60/589,435 | 2004-07-20 | ||
| PCT/CA2005/001115 WO2006007700A1 (en) | 2004-07-20 | 2005-07-15 | Hepatitis c inhibitor dipeptide analogs |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008506719A JP2008506719A (ja) | 2008-03-06 |
| JP2008506719A5 JP2008506719A5 (enExample) | 2008-09-04 |
| JP4914354B2 true JP4914354B2 (ja) | 2012-04-11 |
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| JP2007521757A Expired - Fee Related JP4914354B2 (ja) | 2004-07-20 | 2005-07-15 | Ｃ型肝炎インヒビターペプチド類似体 |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US7511157B2 (enExample) |
| EP (1) | EP1771453B1 (enExample) |
| JP (1) | JP4914354B2 (enExample) |
| AR (1) | AR050430A1 (enExample) |
| CA (1) | CA2573219C (enExample) |
| PE (1) | PE20060381A1 (enExample) |
| TW (1) | TW200615275A (enExample) |
| UY (1) | UY29016A1 (enExample) |
| WO (1) | WO2006007700A1 (enExample) |
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| UA79749C2 (en) | 1996-10-18 | 2007-07-25 | Vertex Pharma | Inhibitors of serine proteases, particularly hepatitis c virus ns3 protease |
| MY140680A (en) | 2002-05-20 | 2010-01-15 | Bristol Myers Squibb Co | Hepatitis c virus inhibitors |
| US7176208B2 (en) | 2003-04-18 | 2007-02-13 | Enanta Pharmaceuticals, Inc. | Quinoxalinyl macrocyclic hepatitis C serine protease inhibitors |
| DE602004010137T2 (de) * | 2003-05-21 | 2008-09-11 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Verbindungen als hepatitis c inhibitoren |
| US7491794B2 (en) * | 2003-10-14 | 2009-02-17 | Intermune, Inc. | Macrocyclic compounds as inhibitors of viral replication |
| UY29016A1 (es) * | 2004-07-20 | 2006-02-24 | Boehringer Ingelheim Int | Analogos de dipeptidos inhibidores de la hepatitis c |
| CA2573346C (en) * | 2004-07-20 | 2011-09-20 | Boehringer Ingelheim International Gmbh | Hepatitis c inhibitor peptide analogs |
| US7323447B2 (en) | 2005-02-08 | 2008-01-29 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| EP1695973A1 (en) * | 2005-02-24 | 2006-08-30 | Neuro3D | Ocaperidone salt and pharmaceutical compositions containing the same |
| US7592336B2 (en) | 2005-05-10 | 2009-09-22 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US7601686B2 (en) | 2005-07-11 | 2009-10-13 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| GEP20105124B (en) * | 2005-07-25 | 2010-11-25 | Array Biopharma Inc | Novel macrocyclic inhibitors of hepatitis c virus replication |
| WO2007019674A1 (en) | 2005-08-12 | 2007-02-22 | Boehringer Ingelheim International Gmbh | Viral polymerase inhibitors |
| AR055395A1 (es) | 2005-08-26 | 2007-08-22 | Vertex Pharma | Compuestos inhibidores de la actividad de la serina proteasa ns3-ns4a del virus de la hepatitis c |
| UA93990C2 (ru) | 2005-10-11 | 2011-03-25 | Интермюн, Инк. | Соединения и способ ингибирования репликации вируса гепатита c |
| US7772183B2 (en) | 2005-10-12 | 2010-08-10 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US7741281B2 (en) | 2005-11-03 | 2010-06-22 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US7816348B2 (en) | 2006-02-03 | 2010-10-19 | Boehringer Ingelheim International Gmbh | Viral polymerase inhibitors |
| KR20090024834A (ko) | 2006-07-05 | 2009-03-09 | 인터뮨, 인크. | Ｃ형 간염 바이러스 복제의 신규 억제제 |
| US7935670B2 (en) | 2006-07-11 | 2011-05-03 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
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| BRPI0716060A2 (pt) | 2006-08-17 | 2013-09-17 | Boehringer Ingelheim Int | inibidores de polimerase viral. |
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- 2005-07-15 CA CA2573219A patent/CA2573219C/en not_active Expired - Fee Related
- 2005-07-15 EP EP05763539A patent/EP1771453B1/en not_active Expired - Lifetime
- 2005-07-15 WO PCT/CA2005/001115 patent/WO2006007700A1/en not_active Ceased
- 2005-07-18 PE PE2005000824A patent/PE20060381A1/es not_active Application Discontinuation
- 2005-07-19 TW TW094124344A patent/TW200615275A/zh unknown
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Patent Citations (6)
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| WO2003064416A1 (en) * | 2002-02-01 | 2003-08-07 | Boehringer Ingelheim International Gmbh | Heterocyclic tripeptides as hepatitis c inhibitors |
| WO2003064456A1 (en) * | 2002-02-01 | 2003-08-07 | Boehringer Ingelheim International Gmbh | Tripeptides having a hydroxyproline ether of a substituted quinoline for the inhibition of ns3 (hepatitis c) |
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Also Published As
| Publication number | Publication date |
|---|---|
| EP1771453B1 (en) | 2012-05-30 |
| CA2573219C (en) | 2011-01-18 |
| US20090156822A1 (en) | 2009-06-18 |
| AR050430A1 (es) | 2006-10-25 |
| TW200615275A (en) | 2006-05-16 |
| PE20060381A1 (es) | 2006-06-01 |
| US7511157B2 (en) | 2009-03-31 |
| US20060046965A1 (en) | 2006-03-02 |
| CA2573219A1 (en) | 2006-01-26 |
| EP1771453A1 (en) | 2007-04-11 |
| JP2008506719A (ja) | 2008-03-06 |
| US7767818B2 (en) | 2010-08-03 |
| EP1771453A4 (en) | 2009-03-18 |
| UY29016A1 (es) | 2006-02-24 |
| WO2006007700A1 (en) | 2006-01-26 |
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