UA77758C2 - Tripeptides with hydroxyproline ester of substituted quinoline useful as inhibitors of hcv ns3 protease for treatment of hepatitis c - Google Patents
Tripeptides with hydroxyproline ester of substituted quinoline useful as inhibitors of hcv ns3 protease for treatment of hepatitis c Download PDFInfo
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- UA77758C2 UA77758C2 UA20040807172A UA20040807172A UA77758C2 UA 77758 C2 UA77758 C2 UA 77758C2 UA 20040807172 A UA20040807172 A UA 20040807172A UA 20040807172 A UA20040807172 A UA 20040807172A UA 77758 C2 UA77758 C2 UA 77758C2
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- compound
- formula
- differs
- cyclopentyl
- tert
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- -1 hydroxyproline ester Chemical class 0.000 title claims abstract description 17
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- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
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- 239000013074 reference sample Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
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- 229960004889 salicylic acid Drugs 0.000 description 1
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- 238000013207 serial dilution Methods 0.000 description 1
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- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
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- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 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
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229960005311 telbivudine Drugs 0.000 description 1
- 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
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical class CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical class C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
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- NZVYCXVTEHPMHE-ZSUJOUNUSA-N thymalfasin Chemical compound CC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(N)=O)C(O)=O NZVYCXVTEHPMHE-ZSUJOUNUSA-N 0.000 description 1
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- 206010043778 thyroiditis Diseases 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-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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Classifications
-
- 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
-
- 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
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/06—Tripeptides
-
- 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
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- 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
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- General Chemical & Material Sciences (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Virology (AREA)
- Gastroenterology & Hepatology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Epidemiology (AREA)
- Immunology (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA002370396A CA2370396A1 (en) | 2002-02-01 | 2002-02-01 | Hepatitis c inhibitor tri-peptides |
| PCT/CA2003/000090 WO2003064456A1 (en) | 2002-02-01 | 2003-01-24 | Tripeptides having a hydroxyproline ether of a substituted quinoline for the inhibition of ns3 (hepatitis c) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA77758C2 true UA77758C2 (en) | 2007-01-15 |
Family
ID=27626587
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA20040807172A UA77758C2 (en) | 2002-02-01 | 2003-01-24 | Tripeptides with hydroxyproline ester of substituted quinoline useful as inhibitors of hcv ns3 protease for treatment of hepatitis c |
Country Status (30)
| Country | Link |
|---|---|
| EP (1) | EP1474441B1 (es) |
| JP (1) | JP4060801B2 (es) |
| KR (1) | KR20040097990A (es) |
| CN (1) | CN100430414C (es) |
| AR (1) | AR038383A1 (es) |
| AT (1) | ATE358137T1 (es) |
| AU (1) | AU2003202347B2 (es) |
| BR (1) | BR0307408A (es) |
| CA (1) | CA2370396A1 (es) |
| CO (1) | CO5611113A2 (es) |
| DE (1) | DE60312824T2 (es) |
| DK (1) | DK1474441T3 (es) |
| EA (1) | EA007742B1 (es) |
| EC (1) | ECSP045226A (es) |
| ES (1) | ES2285085T3 (es) |
| HR (1) | HRP20040697A2 (es) |
| IL (1) | IL163130A (es) |
| MX (1) | MXPA04007515A (es) |
| MY (1) | MY127791A (es) |
| NO (1) | NO20043643L (es) |
| NZ (1) | NZ534689A (es) |
| PE (1) | PE20031012A1 (es) |
| PL (1) | PL371324A1 (es) |
| RS (1) | RS67204A (es) |
| SA (1) | SA03240005B1 (es) |
| TW (1) | TW200400199A (es) |
| UA (1) | UA77758C2 (es) |
| UY (1) | UY27636A1 (es) |
| WO (1) | WO2003064456A1 (es) |
| ZA (1) | ZA200405933B (es) |
Families Citing this family (135)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1337550B1 (en) | 2000-11-20 | 2006-05-24 | Bristol-Myers Squibb Company | Hepatitis c tripeptide inhibitors |
| US6867185B2 (en) | 2001-12-20 | 2005-03-15 | Bristol-Myers Squibb Company | Inhibitors of hepatitis C virus |
| WO2003099316A1 (en) | 2002-05-20 | 2003-12-04 | Bristol-Myers Squibb Company | Heterocyclicsulfonamide hepatitis c virus inhibitors |
| MY140680A (en) | 2002-05-20 | 2010-01-15 | Bristol Myers Squibb Co | Hepatitis c virus inhibitors |
| AU2003299519A1 (en) | 2002-05-20 | 2004-05-04 | Bristol-Myers Squibb Company | Hepatitis c virus inhibitors |
| AU2003301959A1 (en) | 2002-05-20 | 2004-06-03 | Bristol-Myers Squibb Company | Substituted cycloalkyl p1' hepatitis c virus inhibitors |
| WO2004101605A1 (en) * | 2003-03-05 | 2004-11-25 | Boehringer Ingelheim International Gmbh | Hepatitis c inhibiting compounds |
| ATE486889T1 (de) * | 2003-03-05 | 2010-11-15 | Boehringer Ingelheim Int | Peptidanaloga mit inhibitorischer wirkung auf hepatitis c |
| US7176208B2 (en) | 2003-04-18 | 2007-02-13 | Enanta Pharmaceuticals, Inc. | Quinoxalinyl macrocyclic hepatitis C serine protease inhibitors |
| UY28323A1 (es) | 2003-05-21 | 2004-12-31 | Boehringer Ingelheim Int | Compuestos inhibidores de la hepatitis c |
| JP2007506788A (ja) | 2003-09-26 | 2007-03-22 | ライジェル ファーマシューティカルズ， インコーポレイテッド | Ｈｃｖ感染阻害剤とその使用法 |
| NZ546347A (en) | 2003-10-14 | 2009-11-27 | Intermune Inc | Macrocyclic carboxylic acids and acylsulfonamides as inhibitors of HCV replication |
| EP1944042A1 (en) | 2003-10-27 | 2008-07-16 | Vertex Pharmceuticals Incorporated | Combinations for HCV treatment |
| WO2005043118A2 (en) | 2003-10-27 | 2005-05-12 | Vertex Pharmaceuticals Incorporated | Drug discovery method |
| US7132504B2 (en) | 2003-11-12 | 2006-11-07 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US7135462B2 (en) * | 2003-11-20 | 2006-11-14 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US7309708B2 (en) | 2003-11-20 | 2007-12-18 | Birstol-Myers Squibb Company | Hepatitis C virus inhibitors |
| ES2358333T3 (es) | 2004-01-21 | 2011-05-09 | Boehringer Ingelheim International Gmbh | Péptidos macrocíclicos con acción contra el virus de la hepatitis c. |
| WO2005073195A2 (en) | 2004-01-30 | 2005-08-11 | Medivir Ab | Hcv ns-3 serine protease inhibitors |
| TWI368507B (en) | 2004-02-20 | 2012-07-21 | Boehringer Ingelheim Int | Viral polymerase inhibitors |
| US7173057B2 (en) | 2004-02-27 | 2007-02-06 | Schering Corporation | Ketoamides with cyclic P4'S as inhibitors of NS3 protease of hepatitis C virus |
| CA2560897C (en) * | 2004-03-30 | 2012-06-12 | Intermune, Inc. | Macrocyclic compounds as inhibitors of viral replication |
| WO2005121138A2 (en) | 2004-06-03 | 2005-12-22 | Rigel Pharmaceuticals, Inc. | Heterotricyclic compounds for use as hcv inhibitors |
| WO2006000085A1 (en) * | 2004-06-28 | 2006-01-05 | Boehringer Ingelheim International Gmbh | Hepatitis c inhibitor peptide analogs |
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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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| TWI389908B (zh) * | 2005-07-14 | 2013-03-21 | Gilead Sciences Inc | 抗病毒化合物類 |
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| US6323180B1 (en) * | 1998-08-10 | 2001-11-27 | Boehringer Ingelheim (Canada) Ltd | Hepatitis C inhibitor tri-peptides |
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2002
- 2002-02-01 CA CA002370396A patent/CA2370396A1/en not_active Abandoned
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2003
- 2003-01-24 DE DE60312824T patent/DE60312824T2/de not_active Expired - Lifetime
- 2003-01-24 EA EA200400987A patent/EA007742B1/ru not_active IP Right Cessation
- 2003-01-24 EP EP03700744A patent/EP1474441B1/en not_active Expired - Lifetime
- 2003-01-24 JP JP2003564076A patent/JP4060801B2/ja not_active Expired - Fee Related
- 2003-01-24 DK DK03700744T patent/DK1474441T3/da active
- 2003-01-24 CN CNB038061643A patent/CN100430414C/zh not_active Expired - Fee Related
- 2003-01-24 MX MXPA04007515A patent/MXPA04007515A/es active IP Right Grant
- 2003-01-24 UA UA20040807172A patent/UA77758C2/uk unknown
- 2003-01-24 AT AT03700744T patent/ATE358137T1/de active
- 2003-01-24 AU AU2003202347A patent/AU2003202347B2/en not_active Ceased
- 2003-01-24 NZ NZ534689A patent/NZ534689A/en not_active IP Right Cessation
- 2003-01-24 KR KR10-2004-7011771A patent/KR20040097990A/ko active IP Right Grant
- 2003-01-24 RS YU67204A patent/RS67204A/sr unknown
- 2003-01-24 BR BR0307408-0A patent/BR0307408A/pt not_active IP Right Cessation
- 2003-01-24 PL PL03371324A patent/PL371324A1/xx not_active Application Discontinuation
- 2003-01-24 WO PCT/CA2003/000090 patent/WO2003064456A1/en active IP Right Grant
- 2003-01-24 ES ES03700744T patent/ES2285085T3/es not_active Expired - Lifetime
- 2003-01-30 PE PE2003000104A patent/PE20031012A1/es not_active Application Discontinuation
- 2003-01-30 TW TW092102241A patent/TW200400199A/zh unknown
- 2003-01-31 MY MYPI20030357A patent/MY127791A/en unknown
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- 2003-01-31 UY UY27636A patent/UY27636A1/es not_active Application Discontinuation
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- 2004-07-26 ZA ZA200405933A patent/ZA200405933B/en unknown
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- 2004-08-09 EC EC2004005226A patent/ECSP045226A/es unknown
- 2004-08-31 CO CO04085344A patent/CO5611113A2/es not_active Application Discontinuation
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| HRP20040697A2 (en) | 2005-06-30 |
| UY27636A1 (es) | 2003-09-30 |
| WO2003064456A1 (en) | 2003-08-07 |
| PL371324A1 (en) | 2005-06-13 |
| CN1642974A (zh) | 2005-07-20 |
| NZ534689A (en) | 2007-05-31 |
| DE60312824T2 (de) | 2008-03-06 |
| EA200400987A1 (ru) | 2005-02-24 |
| PE20031012A1 (es) | 2004-01-26 |
| NO20043643L (no) | 2004-08-31 |
| BR0307408A (pt) | 2004-12-28 |
| JP4060801B2 (ja) | 2008-03-12 |
| EA007742B1 (ru) | 2006-12-29 |
| AR038383A1 (es) | 2005-01-12 |
| EP1474441B1 (en) | 2007-03-28 |
| IL163130A (en) | 2010-06-30 |
| MXPA04007515A (es) | 2005-07-13 |
| MY127791A (en) | 2006-12-29 |
| ZA200405933B (en) | 2005-09-05 |
| DK1474441T3 (da) | 2007-07-30 |
| DE60312824D1 (de) | 2007-05-10 |
| SA03240005B1 (ar) | 2008-04-15 |
| CN100430414C (zh) | 2008-11-05 |
| CA2370396A1 (en) | 2003-08-01 |
| EP1474441A1 (en) | 2004-11-10 |
| RS67204A (en) | 2006-12-15 |
| AU2003202347B2 (en) | 2008-10-30 |
| ES2285085T3 (es) | 2007-11-16 |
| KR20040097990A (ko) | 2004-11-18 |
| ECSP045226A (es) | 2004-09-28 |
| TW200400199A (en) | 2004-01-01 |
| JP2005530688A (ja) | 2005-10-13 |
| CO5611113A2 (es) | 2006-02-28 |
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