CA2429359A1 - Hepatitis c tripeptide inhibitors - Google Patents
Hepatitis c tripeptide inhibitors Download PDFInfo
- Publication number
- CA2429359A1 CA2429359A1 CA002429359A CA2429359A CA2429359A1 CA 2429359 A1 CA2429359 A1 CA 2429359A1 CA 002429359 A CA002429359 A CA 002429359A CA 2429359 A CA2429359 A CA 2429359A CA 2429359 A1 CA2429359 A1 CA 2429359A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- amido
- compound
- optionally substituted
- phenyl
- 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.)
- Abandoned
Links
- 239000003112 inhibitor Substances 0.000 title description 8
- 208000006454 hepatitis Diseases 0.000 title description 3
- 231100000283 hepatitis Toxicity 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 311
- 238000000034 method Methods 0.000 claims abstract description 216
- 238000011282 treatment Methods 0.000 claims abstract description 20
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 14
- 208000015181 infectious disease Diseases 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 106
- 125000003368 amide group Chemical group 0.000 claims description 97
- -1 nitro, pyridyl Chemical group 0.000 claims description 77
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 75
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 66
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- 239000000651 prodrug Substances 0.000 claims description 35
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 34
- 239000012453 solvate Substances 0.000 claims description 30
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 29
- 125000003118 aryl group Chemical group 0.000 claims description 28
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 27
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 27
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- 125000003710 aryl alkyl group Chemical group 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 15
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- MKCBRYIXFFGIKN-UHFFFAOYSA-N bicyclo[1.1.1]pentane Chemical compound C1C2CC1C2 MKCBRYIXFFGIKN-UHFFFAOYSA-N 0.000 claims description 2
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- ZXUQEPZWVQIOJE-UHFFFAOYSA-N methyl 2-chloro-2-oxoacetate Chemical compound COC(=O)C(Cl)=O ZXUQEPZWVQIOJE-UHFFFAOYSA-N 0.000 description 1
- STZTVHPWCYAYEU-UHFFFAOYSA-N methyl 4-(7-methoxy-2-phenylquinolin-4-yl)oxy-1-[3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoyl]pyrrolidine-2-carboxylate Chemical compound C1N(C(=O)C(NC(=O)OC(C)(C)C)C(C)C)C(C(=O)OC)CC1OC1=CC(C=2C=CC=CC=2)=NC2=CC(OC)=CC=C12 STZTVHPWCYAYEU-UHFFFAOYSA-N 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
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- UWHWNFVVODLFIQ-UHFFFAOYSA-N methyl pyrrolidine-1-carboxylate Chemical compound COC(=O)N1CCCC1 UWHWNFVVODLFIQ-UHFFFAOYSA-N 0.000 description 1
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- IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 description 1
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- 230000006337 proteolytic cleavage Effects 0.000 description 1
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- 229960000948 quinine Drugs 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- SYBXSZMNKDOUCA-UHFFFAOYSA-J rhodium(2+);tetraacetate Chemical compound [Rh+2].[Rh+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O SYBXSZMNKDOUCA-UHFFFAOYSA-J 0.000 description 1
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- 238000012216 screening Methods 0.000 description 1
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- 239000003001 serine protease inhibitor Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000002415 sodium dodecyl sulfate polyacrylamide gel electrophoresis Methods 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- OIRNAOWGCPSZCJ-UHFFFAOYSA-N spiro[2.3]hexan-6-one Chemical compound O=C1CCC11CC1 OIRNAOWGCPSZCJ-UHFFFAOYSA-N 0.000 description 1
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- 238000010254 subcutaneous injection Methods 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
- QAHVHSLSRLSVGS-UHFFFAOYSA-N sulfamoyl chloride Chemical compound NS(Cl)(=O)=O QAHVHSLSRLSVGS-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Chemical group 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
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- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DMPRLQGGRJZPDN-LRDDRELGSA-N tert-butyl (1s,2s)-2-ethyl-1-(2-trimethylsilylethoxycarbonylamino)cyclopropane-1-carboxylate Chemical compound CC[C@H]1C[C@@]1(NC(=O)OCC[Si](C)(C)C)C(=O)OC(C)(C)C DMPRLQGGRJZPDN-LRDDRELGSA-N 0.000 description 1
- WEWZMCDCBQUJIW-IBMVUYFASA-N tert-butyl (2s,4r)-2-[[(1r,2s)-1-(cyclopropylsulfonylcarbamoyl)-2-ethenylcyclopropyl]carbamoyl]-4-(7-methoxy-2-phenylquinolin-4-yl)oxypyrrolidine-1-carboxylate Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)OC(C)(C)C)OC=1C2=CC=C(C=C2N=C(C=1)C=1C=CC=CC=1)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C WEWZMCDCBQUJIW-IBMVUYFASA-N 0.000 description 1
- HUWKXMNDWIOLPB-UHFFFAOYSA-N tert-butyl 2-[[1-(cyclopropylsulfonylcarbamoyl)-2-ethylcyclopropyl]carbamoyl]-4-(7-methoxy-2-phenylquinolin-4-yl)oxypyrrolidine-1-carboxylate Chemical compound CCC1CC1(C(=O)NS(=O)(=O)C1CC1)NC(=O)C1N(C(=O)OC(C)(C)C)CC(OC=2C3=CC=C(OC)C=C3N=C(C=2)C=2C=CC=CC=2)C1 HUWKXMNDWIOLPB-UHFFFAOYSA-N 0.000 description 1
- UOUFRTFWWBCVPV-UHFFFAOYSA-N tert-butyl 4-(2,4-dioxo-1H-thieno[3,2-d]pyrimidin-3-yl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(CC1)n1c(=O)[nH]c2ccsc2c1=O UOUFRTFWWBCVPV-UHFFFAOYSA-N 0.000 description 1
- MFPWEWYKQYMWRO-UHFFFAOYSA-N tert-butyl carboxy carbonate Chemical compound CC(C)(C)OC(=O)OC(O)=O MFPWEWYKQYMWRO-UHFFFAOYSA-N 0.000 description 1
- LPQZERIRKRYGGM-UHFFFAOYSA-N tert-butyl pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCC1 LPQZERIRKRYGGM-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
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- 206010043778 thyroiditis Diseases 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000002627 tracheal intubation Methods 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
- 230000009466 transformation Effects 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 125000006000 trichloroethyl group Chemical group 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 1
- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 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
- 229960000281 trometamol Drugs 0.000 description 1
- 229960004441 tyrosine Drugs 0.000 description 1
- 238000005199 ultracentrifugation Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 229960004295 valine Drugs 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
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
- C07K5/0827—Tripeptides containing heteroatoms different from O, S, or N
-
- 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
-
- 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
- C07K5/08—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
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Virology (AREA)
- Engineering & Computer Science (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Gastroenterology & Hepatology (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Treating Waste Gases (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US24996800P | 2000-11-20 | 2000-11-20 | |
| US60/249,968 | 2000-11-20 | ||
| PCT/US2001/045145 WO2002060926A2 (en) | 2000-11-20 | 2001-11-20 | Hepatitis c tripeptide inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2429359A1 true CA2429359A1 (en) | 2002-08-08 |
Family
ID=22945765
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002429359A Abandoned CA2429359A1 (en) | 2000-11-20 | 2001-11-20 | Hepatitis c tripeptide inhibitors |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US6872805B2 (https=) |
| EP (1) | EP1337550B1 (https=) |
| JP (1) | JP3889708B2 (https=) |
| CN (1) | CN100391967C (https=) |
| AT (1) | ATE327246T1 (https=) |
| AU (1) | AU2002248147B2 (https=) |
| BR (1) | BR0115447A (https=) |
| CA (1) | CA2429359A1 (https=) |
| DE (1) | DE60119968T2 (https=) |
| ES (1) | ES2263687T3 (https=) |
| HU (1) | HUP0500456A3 (https=) |
| MX (1) | MXPA03004299A (https=) |
| PE (1) | PE20020707A1 (https=) |
| WO (1) | WO2002060926A2 (https=) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006007700A1 (en) * | 2004-07-20 | 2006-01-26 | Boehringer Ingelheim International Gmbh | Hepatitis c inhibitor dipeptide analogs |
| US7585845B2 (en) | 2003-05-21 | 2009-09-08 | Boehringer Ingelheim International Gmbh | Hepatitis C inhibitor compounds |
| US7696242B2 (en) | 2004-07-20 | 2010-04-13 | Boehringer Ingelheim International Gmbh | Hepatitis C inhibitor peptide analogs |
| US8178491B2 (en) | 2007-06-29 | 2012-05-15 | Gilead Sciences, Inc. | Antiviral compounds |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6323180B1 (en) * | 1998-08-10 | 2001-11-27 | Boehringer Ingelheim (Canada) Ltd | Hepatitis C inhibitor tri-peptides |
| CA2369711A1 (en) | 2002-01-30 | 2003-07-30 | Boehringer Ingelheim (Canada) Ltd. | Macrocyclic peptides active against the hepatitis c virus |
| CA2370396A1 (en) | 2002-02-01 | 2003-08-01 | Boehringer Ingelheim (Canada) Ltd. | Hepatitis c inhibitor tri-peptides |
| CA2369970A1 (en) | 2002-02-01 | 2003-08-01 | Boehringer Ingelheim (Canada) Ltd. | Hepatitis c inhibitor tri-peptides |
| US6828301B2 (en) | 2002-02-07 | 2004-12-07 | Boehringer Ingelheim International Gmbh | Pharmaceutical compositions for hepatitis C viral protease inhibitors |
-
2001
- 2001-11-20 DE DE60119968T patent/DE60119968T2/de not_active Expired - Lifetime
- 2001-11-20 WO PCT/US2001/045145 patent/WO2002060926A2/en not_active Ceased
- 2001-11-20 ES ES01997024T patent/ES2263687T3/es not_active Expired - Lifetime
- 2001-11-20 BR BR0115447-8A patent/BR0115447A/pt not_active Application Discontinuation
- 2001-11-20 AU AU2002248147A patent/AU2002248147B2/en not_active Ceased
- 2001-11-20 EP EP01997024A patent/EP1337550B1/en not_active Expired - Lifetime
- 2001-11-20 CA CA002429359A patent/CA2429359A1/en not_active Abandoned
- 2001-11-20 MX MXPA03004299A patent/MXPA03004299A/es active IP Right Grant
- 2001-11-20 CN CNB018221106A patent/CN100391967C/zh not_active Expired - Fee Related
- 2001-11-20 US US10/001,850 patent/US6872805B2/en not_active Expired - Lifetime
- 2001-11-20 PE PE2001001155A patent/PE20020707A1/es not_active Application Discontinuation
- 2001-11-20 HU HU0500456A patent/HUP0500456A3/hu unknown
- 2001-11-20 AT AT01997024T patent/ATE327246T1/de not_active IP Right Cessation
- 2001-11-20 JP JP2002561494A patent/JP3889708B2/ja not_active Expired - Fee Related
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7585845B2 (en) | 2003-05-21 | 2009-09-08 | Boehringer Ingelheim International Gmbh | Hepatitis C inhibitor compounds |
| US7939667B2 (en) | 2003-05-21 | 2011-05-10 | Boehringer Ingelheim International Gmbh | Hepatitis C inhibitor compounds |
| US8067438B2 (en) | 2003-05-21 | 2011-11-29 | Boehringer Ingelheim International Gmbh | Hepatitis C inhibitor compounds |
| WO2006007700A1 (en) * | 2004-07-20 | 2006-01-26 | Boehringer Ingelheim International Gmbh | Hepatitis c inhibitor dipeptide analogs |
| US7511157B2 (en) | 2004-07-20 | 2009-03-31 | Boehringer Ingelheim International Gmbh | Hepatitis C inhibitor dipeptide analogs |
| US7696242B2 (en) | 2004-07-20 | 2010-04-13 | Boehringer Ingelheim International Gmbh | Hepatitis C inhibitor peptide analogs |
| US7767818B2 (en) | 2004-07-20 | 2010-08-03 | Boehringer Ingelheim International Gmbh | Hepatitis C inhibitor dipeptide analogs |
| US8178491B2 (en) | 2007-06-29 | 2012-05-15 | Gilead Sciences, Inc. | Antiviral compounds |
| US8513186B2 (en) | 2007-06-29 | 2013-08-20 | Gilead Sciences, Inc. | Antiviral compounds |
| US8809267B2 (en) | 2007-06-29 | 2014-08-19 | Gilead Sciences, Inc. | Antiviral compounds |
| US8809266B2 (en) | 2007-06-29 | 2014-08-19 | Gilead Sciences, Inc. | Antiviral compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1531547A (zh) | 2004-09-22 |
| WO2002060926A2 (en) | 2002-08-08 |
| PE20020707A1 (es) | 2002-08-11 |
| US20020111313A1 (en) | 2002-08-15 |
| ATE327246T1 (de) | 2006-06-15 |
| WO2002060926A3 (en) | 2003-03-13 |
| AU2002248147B2 (en) | 2006-04-06 |
| BR0115447A (pt) | 2005-10-18 |
| US6872805B2 (en) | 2005-03-29 |
| DE60119968T2 (de) | 2007-01-18 |
| DE60119968D1 (en) | 2006-06-29 |
| ES2263687T3 (es) | 2006-12-16 |
| EP1337550B1 (en) | 2006-05-24 |
| JP3889708B2 (ja) | 2007-03-07 |
| EP1337550A2 (en) | 2003-08-27 |
| JP2004538251A (ja) | 2004-12-24 |
| HUP0500456A3 (en) | 2012-05-02 |
| HUP0500456A2 (hu) | 2005-08-29 |
| MXPA03004299A (es) | 2004-02-12 |
| CN100391967C (zh) | 2008-06-04 |
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