RU2002131163A - Макроциклические ингибиторы ns3-серинпротезы вируса гепатита с, содержащие алкил- и арилаланиновые p2 фрагменты - Google Patents
Макроциклические ингибиторы ns3-серинпротезы вируса гепатита с, содержащие алкил- и арилаланиновые p2 фрагменты Download PDFInfo
- Publication number
- RU2002131163A RU2002131163A RU2002131163/04A RU2002131163A RU2002131163A RU 2002131163 A RU2002131163 A RU 2002131163A RU 2002131163/04 A RU2002131163/04 A RU 2002131163/04A RU 2002131163 A RU2002131163 A RU 2002131163A RU 2002131163 A RU2002131163 A RU 2002131163A
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- Prior art keywords
- alkyl
- conhch
- group
- aryl
- compound
- Prior art date
Links
- 239000012634 fragment Substances 0.000 title claims 7
- 208000006454 hepatitis Diseases 0.000 title 1
- 231100000283 hepatitis Toxicity 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 230000003612 virological effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 32
- 125000000217 alkyl group Chemical group 0.000 claims 25
- -1 enantiomers Chemical class 0.000 claims 21
- 125000003118 aryl group Chemical group 0.000 claims 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims 9
- 229910052760 oxygen Inorganic materials 0.000 claims 9
- 239000008194 pharmaceutical composition Substances 0.000 claims 9
- 229910005965 SO 2 Inorganic materials 0.000 claims 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims 7
- 125000004404 heteroalkyl group Chemical group 0.000 claims 7
- 125000001072 heteroaryl group Chemical group 0.000 claims 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 6
- 125000002877 alkyl aryl group Chemical group 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- 108091005804 Peptidases Proteins 0.000 claims 4
- 239000004365 Protease Substances 0.000 claims 4
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 claims 4
- 235000013877 carbamide Nutrition 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 3
- 150000001408 amides Chemical class 0.000 claims 3
- 150000001412 amines Chemical class 0.000 claims 3
- 239000004202 carbamide Substances 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 239000003937 drug carrier Substances 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
- 102000014150 Interferons Human genes 0.000 claims 2
- 108010050904 Interferons Proteins 0.000 claims 2
- 150000001299 aldehydes Chemical class 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000004422 alkyl sulphonamide group Chemical group 0.000 claims 2
- 230000000840 anti-viral effect Effects 0.000 claims 2
- 125000004104 aryloxy group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 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 2
- 125000004185 ester group Chemical group 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 229940079322 interferon Drugs 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- RGICCULPCWNRAB-UHFFFAOYSA-N 2-[2-(2-hexoxyethoxy)ethoxy]ethanol Chemical compound CCCCCCOCCOCCOCCO RGICCULPCWNRAB-UHFFFAOYSA-N 0.000 claims 1
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 208000005176 Hepatitis C Diseases 0.000 claims 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
- 102000006992 Interferon-alpha Human genes 0.000 claims 1
- 108010047761 Interferon-alpha Proteins 0.000 claims 1
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 229940100389 Sulfonylurea Drugs 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 150000003973 alkyl amines Chemical class 0.000 claims 1
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- 150000005215 alkyl ethers Chemical class 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 150000004982 aromatic amines Chemical class 0.000 claims 1
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims 1
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 1
- 150000008378 aryl ethers Chemical class 0.000 claims 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- UZMZVDOOVXLRID-UHFFFAOYSA-N azanylidyne-(nitrosulfonylamino)methane Chemical compound [O-][N+](=O)S(=O)(=O)NC#N UZMZVDOOVXLRID-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 125000005222 heteroarylaminocarbonyl group Chemical group 0.000 claims 1
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims 1
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 150000002678 macrocyclic compounds Chemical class 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000002560 nitrile group Chemical group 0.000 claims 1
- MGQNMYSRDBFUIR-UHFFFAOYSA-N nitro cyanoformate Chemical group [O-][N+](=O)OC(=O)C#N MGQNMYSRDBFUIR-UHFFFAOYSA-N 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 125000004437 phosphorous atom Chemical group 0.000 claims 1
- 125000005936 piperidyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 229960000329 ribavirin Drugs 0.000 claims 1
- 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 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims 1
- 150000003462 sulfoxides Chemical class 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea group Chemical group NC(=S)N UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims 1
- 0 CC1CC2C(*)(*)C2C1 Chemical compound CC1CC2C(*)(*)C2C1 0.000 description 3
- GTZUVNLKUABXMM-WKGQYQEVSA-N CCCC(C(C(NCC(NC(C(N)=O)c1ccccc1)=O)=O)=O)NC([C@H](CCCCNC(CCC(NC(CC(O)=O)C(NC1CC2CCCCC2)=O)=O)=O)NC1=O)=O Chemical compound CCCC(C(C(NCC(NC(C(N)=O)c1ccccc1)=O)=O)=O)NC([C@H](CCCCNC(CCC(NC(CC(O)=O)C(NC1CC2CCCCC2)=O)=O)=O)NC1=O)=O GTZUVNLKUABXMM-WKGQYQEVSA-N 0.000 description 1
- AOJSPCTVPXKPGL-DXMVTJQJSA-N CCCC(C(C(NCC(NC(C(O)=O)c1ccccc1)=O)=O)=O)NC(C([C@H](C)c1cccc(Oc2ccc(CCC(N[C@H]3C)=O)cc2)c1)NC3=O)=O Chemical compound CCCC(C(C(NCC(NC(C(O)=O)c1ccccc1)=O)=O)=O)NC(C([C@H](C)c1cccc(Oc2ccc(CCC(N[C@H]3C)=O)cc2)c1)NC3=O)=O AOJSPCTVPXKPGL-DXMVTJQJSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
- C07K5/0202—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -NH-X-X-C(=0)-, X being an optionally substituted carbon atom or a heteroatom, e.g. beta-amino acids
-
- 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
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/02—Linear peptides containing at least one abnormal peptide link
-
- 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)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biophysics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Virology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US19820400P | 2000-04-19 | 2000-04-19 | |
| US60/198,204 | 2000-04-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2002131163A true RU2002131163A (ru) | 2004-06-27 |
Family
ID=22732422
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2002131163/04A RU2002131163A (ru) | 2000-04-19 | 2001-04-17 | Макроциклические ингибиторы ns3-серинпротезы вируса гепатита с, содержащие алкил- и арилаланиновые p2 фрагменты |
Country Status (22)
Families Citing this family (134)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EA001915B1 (ru) * | 1996-10-18 | 2001-10-22 | Вертекс Фармасьютикалз Инкорпорейтед | Ингибиторы серин-протеаз, в частности ns3 протеазы вируса гепатита c (hvc) |
| US6608027B1 (en) | 1999-04-06 | 2003-08-19 | Boehringer Ingelheim (Canada) Ltd | Macrocyclic peptides active against the hepatitis C virus |
| SV2003000617A (es) | 2000-08-31 | 2003-01-13 | Lilly Co Eli | Inhibidores de la proteasa peptidomimetica ref. x-14912m |
| EP1343807B1 (en) * | 2000-12-12 | 2009-04-29 | Schering Corporation | Diaryl peptides as ns3-serine protease inhibitors of hepatits c virus |
| BR0206614A (pt) | 2001-01-22 | 2004-02-17 | Merck & Co Inc | Composto, composição farmacêutica, método para inibir a polimerase viral de rna dependente de rna e/ou inibir a replicação viral de rna dependente de rna, método para tratar uma infecção viral de rna dependente de rna, e, uso de um composto |
| US7119072B2 (en) | 2002-01-30 | 2006-10-10 | Boehringer Ingelheim (Canada) Ltd. | Macrocyclic peptides active against the hepatitis C virus |
| US7091184B2 (en) | 2002-02-01 | 2006-08-15 | Boehringer Ingelheim International Gmbh | Hepatitis C inhibitor tri-peptides |
| US6642204B2 (en) | 2002-02-01 | 2003-11-04 | Boehringer Ingelheim International Gmbh | Hepatitis C inhibitor tri-peptides |
| EP1497282A2 (en) * | 2002-04-11 | 2005-01-19 | Vertex Pharmaceuticals Incorporated | Inhibitors of serine protease, particularly hepatitis c virus ns3-ns4 protease |
| US20050075279A1 (en) | 2002-10-25 | 2005-04-07 | Boehringer Ingelheim International Gmbh | Macrocyclic peptides active against the hepatitis C virus |
| EP1654261B1 (en) | 2003-05-21 | 2007-11-14 | Boehringer Ingelheim International GmbH | Hepatitis c inhibitor compounds |
| US7476653B2 (en) * | 2003-06-18 | 2009-01-13 | Tranzyme Pharma, Inc. | Macrocyclic modulators of the ghrelin receptor |
| US8921521B2 (en) | 2003-06-18 | 2014-12-30 | Ocera Therapeutics, Inc. | Macrocyclic modulators of the Ghrelin receptor |
| CA2528375C (en) | 2003-06-18 | 2013-11-19 | Tranzyme Pharma, Inc. | Macrocyclic antagonists of the motilin receptor |
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| TW201127828A (en) * | 2003-09-05 | 2011-08-16 | Vertex Pharma | Inhibitors of serine proteases, particularly HCV NS3-NS4A protease |
| DE602004031645D1 (de) | 2003-09-22 | 2011-04-14 | Boehringer Ingelheim Pharma | Makrozyklische peptide mit wirkung gegen das hepatitis-c-virus |
| EP1664092B1 (en) | 2003-09-26 | 2011-02-02 | Schering Corporation | Macrocyclic inhibitors of hepatitis c virus ns3 serine protease |
| CA2541634A1 (en) | 2003-10-10 | 2005-04-28 | Vertex Pharmaceuticals Incorporated | Inhibitors of serine proteases, particularly hcv ns3-ns4a protease |
| US7491794B2 (en) * | 2003-10-14 | 2009-02-17 | Intermune, Inc. | Macrocyclic compounds as inhibitors of viral replication |
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| WO2005070955A1 (en) | 2004-01-21 | 2005-08-04 | Boehringer Ingelheim International Gmbh | Macrocyclic peptides active against the hepatitis c virus |
| EP1711515A2 (en) | 2004-02-04 | 2006-10-18 | Vertex Pharmaceuticals Incorporated | Inhibitors of serine proteases, particularly hcv ns3-ns4a protease |
| KR20060124725A (ko) | 2004-02-27 | 2006-12-05 | 쉐링 코포레이션 | Ｃ형 간염 바이러스 ｎｓ3 프로테아제의 억제제 |
| CN1972956A (zh) | 2004-02-27 | 2007-05-30 | 先灵公司 | 用作丙型肝炎病毒ns3丝氨酸蛋白酶抑制剂的新化合物 |
| RU2428428C9 (ru) | 2004-02-27 | 2012-03-10 | Шеринг Корпорейшн | Серусодержащие соединения, действующие как ингибиторы сериновой протеазы ns3 вируса гепатита с |
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| EP1737821B1 (en) | 2004-02-27 | 2009-08-05 | Schering Corporation | 3,4-(cyclopentyl)-fused proline compounds as inhibitors of hepatitis c virus ns3 serine protease |
| CN1984922A (zh) | 2004-05-20 | 2007-06-20 | 先灵公司 | 用作丙型肝炎病毒ns3丝氨酸蛋白酶抑制剂的取代脯氨酸 |
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| WO2006007708A1 (en) | 2004-07-20 | 2006-01-26 | Boehringer Engelheim International Gmbh | Hepatitis c inhibitor peptide analogs |
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- 2001-04-17 JP JP2001578418A patent/JP4748912B2/ja not_active Expired - Fee Related
- 2001-04-17 BR BR0110104-8A patent/BR0110104A/pt not_active IP Right Cessation
- 2001-04-17 HK HK03100478.8A patent/HK1048479A1/zh unknown
- 2001-04-17 AR ARP010101794A patent/AR030558A1/es unknown
- 2001-04-17 EP EP01927142A patent/EP1274724A2/en not_active Withdrawn
- 2001-04-17 CA CA002406532A patent/CA2406532A1/en not_active Abandoned
- 2001-04-17 PE PE2001000348A patent/PE20011288A1/es not_active Application Discontinuation
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- 2001-04-17 SK SK1495-2002A patent/SK14952002A3/sk not_active Application Discontinuation
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| ZA200208014B (en) | 2004-02-12 |
| SK14952002A3 (sk) | 2003-03-04 |
| CN101580536A (zh) | 2009-11-18 |
| HK1048479A1 (zh) | 2003-04-04 |
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| US6914122B2 (en) | 2005-07-05 |
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| NO20025030D0 (no) | 2002-10-18 |
| NO20025030L (no) | 2002-12-18 |
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| WO2001081325A3 (en) | 2002-08-01 |
| EP1274724A2 (en) | 2003-01-15 |
| HUP0302957A2 (hu) | 2003-12-29 |
| CN1935833A (zh) | 2007-03-28 |
| IL151935A0 (en) | 2003-04-10 |
| AR030558A1 (es) | 2003-08-27 |
| US20020016294A1 (en) | 2002-02-07 |
| PE20011288A1 (es) | 2001-12-12 |
| CA2406532A1 (en) | 2001-11-01 |
| WO2001081325A2 (en) | 2001-11-01 |
| PL358591A1 (en) | 2004-08-09 |
| JP2003531199A (ja) | 2003-10-21 |
| MXPA02010375A (es) | 2003-04-25 |
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