RU2002129564A - Макроциклические ингибиторы сериновой ns3-протеазы, включающие n-циклические р2 структурные элементы вируса гепатита с - Google Patents
Макроциклические ингибиторы сериновой ns3-протеазы, включающие n-циклические р2 структурные элементы вируса гепатита с Download PDFInfo
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- RU2002129564A RU2002129564A RU2002129564/04A RU2002129564A RU2002129564A RU 2002129564 A RU2002129564 A RU 2002129564A RU 2002129564/04 A RU2002129564/04 A RU 2002129564/04A RU 2002129564 A RU2002129564 A RU 2002129564A RU 2002129564 A RU2002129564 A RU 2002129564A
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- Prior art keywords
- group
- alkyl
- chr
- conhch
- aryl
- Prior art date
Links
- 241000711549 Hepacivirus C Species 0.000 title claims 7
- 239000004365 Protease Substances 0.000 title claims 6
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 36
- 125000000217 alkyl group Chemical group 0.000 claims 30
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 19
- 125000004432 carbon atom Chemical group C* 0.000 claims 14
- -1 enantiomers Chemical class 0.000 claims 14
- 229910052760 oxygen Inorganic materials 0.000 claims 12
- 125000003118 aryl group Chemical group 0.000 claims 11
- 229910052717 sulfur Inorganic materials 0.000 claims 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims 10
- 229910052757 nitrogen Inorganic materials 0.000 claims 10
- 239000001301 oxygen Substances 0.000 claims 9
- 239000008194 pharmaceutical composition Substances 0.000 claims 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- 125000004434 sulfur atom Chemical group 0.000 claims 7
- 125000002877 alkyl aryl group Chemical group 0.000 claims 6
- 239000012634 fragment Substances 0.000 claims 6
- 125000001072 heteroaryl group Chemical group 0.000 claims 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 6
- 108091005804 Peptidases Proteins 0.000 claims 5
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 claims 5
- 229910005965 SO 2 Inorganic materials 0.000 claims 5
- 125000003342 alkenyl group Chemical group 0.000 claims 5
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 5
- 125000003277 amino group Chemical group 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 208000035475 disorder Diseases 0.000 claims 5
- 125000004404 heteroalkyl group Chemical group 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims 4
- 125000004437 phosphorous atom Chemical group 0.000 claims 4
- 125000001174 sulfone group Chemical group 0.000 claims 4
- 239000011593 sulfur Substances 0.000 claims 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 239000004202 carbamide Substances 0.000 claims 3
- 235000013877 carbamide Nutrition 0.000 claims 3
- 239000003937 drug carrier Substances 0.000 claims 3
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 229910052698 phosphorus Inorganic materials 0.000 claims 3
- 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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 102000014150 Interferons Human genes 0.000 claims 2
- 108010050904 Interferons Proteins 0.000 claims 2
- 150000007945 N-acyl ureas Chemical class 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 125000004947 alkyl aryl amino group Chemical group 0.000 claims 2
- 150000001346 alkyl aryl ethers Chemical class 0.000 claims 2
- 150000005215 alkyl ethers Chemical group 0.000 claims 2
- 125000004422 alkyl sulphonamide group Chemical group 0.000 claims 2
- 150000001356 alkyl thiols Chemical class 0.000 claims 2
- 125000003368 amide group Chemical group 0.000 claims 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims 2
- 239000003443 antiviral agent Substances 0.000 claims 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 2
- 125000004104 aryloxy group Chemical group 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000004185 ester group Chemical group 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 125000000524 functional group Chemical group 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 229940079322 interferon Drugs 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 125000004963 sulfonylalkyl group Chemical group 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 2
- RGICCULPCWNRAB-UHFFFAOYSA-N 2-[2-(2-hexoxyethoxy)ethoxy]ethanol Chemical compound CCCCCCOCCOCCOCCO RGICCULPCWNRAB-UHFFFAOYSA-N 0.000 claims 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 102000006992 Interferon-alpha Human genes 0.000 claims 1
- 108010047761 Interferon-alpha Proteins 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
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000003172 aldehyde group Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims 1
- 125000001769 aryl amino group Chemical group 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
- 125000004421 aryl sulphonamide group Chemical group 0.000 claims 1
- 125000002910 aryl thiol group Chemical group 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
- 150000001721 carbon Chemical group 0.000 claims 1
- 238000004177 carbon cycle Methods 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 230000018044 dehydration Effects 0.000 claims 1
- 238000006297 dehydration reaction Methods 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 230000001747 exhibiting effect Effects 0.000 claims 1
- 125000006343 heptafluoro propyl group Chemical group 0.000 claims 1
- 125000005222 heteroarylaminocarbonyl group Chemical group 0.000 claims 1
- 125000005226 heteroaryloxycarbonyl 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
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 125000000468 ketone group Chemical group 0.000 claims 1
- 150000002678 macrocyclic compounds Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000002560 nitrile group Chemical group 0.000 claims 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims 1
- 125000005936 piperidyl 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
- 238000006467 substitution reaction Methods 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 150000003462 sulfoxides Chemical class 0.000 claims 1
- 125000000101 thioether group Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 0 CCONN(C(C*C)I**C(C)=O)NC(C)C(C)=O Chemical compound CCONN(C(C*C)I**C(C)=O)NC(C)C(C)=O 0.000 description 10
- MDWGGFXWOMSTGW-IPZJAAJSSA-N C=CC/C=C/C(C(C(NCC=C)=O)=O)NC([C@H](C[C@H](C1)O[C@@H](CCOc2cccc(CC(NC3)=O)c2)I)N1C3=O)=O Chemical compound C=CC/C=C/C(C(C(NCC=C)=O)=O)NC([C@H](C[C@H](C1)O[C@@H](CCOc2cccc(CC(NC3)=O)c2)I)N1C3=O)=O MDWGGFXWOMSTGW-IPZJAAJSSA-N 0.000 description 1
- SXEGBGAFUPBIHI-LYEKLTKTSA-N CC(C)/[O]=C(/[C@H](CCC1)N1C(C(C1CCCCC1)NC(N(C)Cc1cccc(OCCCO)c1)=O)=O)\NCC(C(NCC(N[C@H](C(N(C)C)=O)c1ccccc1)=O)=O)=O Chemical compound CC(C)/[O]=C(/[C@H](CCC1)N1C(C(C1CCCCC1)NC(N(C)Cc1cccc(OCCCO)c1)=O)=O)\NCC(C(NCC(N[C@H](C(N(C)C)=O)c1ccccc1)=O)=O)=O SXEGBGAFUPBIHI-LYEKLTKTSA-N 0.000 description 1
- YWXPJDOCQDRPKF-BVVFMGSASA-N CCCC(C(C(NCC=C)=O)=O)NC(C(CCC1)N1C([C@H](C)NC(Cc1cccc(OCCCC(O)O)c1)=O)=O)=O Chemical compound CCCC(C(C(NCC=C)=O)=O)NC(C(CCC1)N1C([C@H](C)NC(Cc1cccc(OCCCC(O)O)c1)=O)=O)=O YWXPJDOCQDRPKF-BVVFMGSASA-N 0.000 description 1
- QZFIPQMHETZRKY-UHFFFAOYSA-N CCS(c1cc(C)ccc1)(=O)=O Chemical compound CCS(c1cc(C)ccc1)(=O)=O QZFIPQMHETZRKY-UHFFFAOYSA-N 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
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
-
- 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
- C07K5/12—Cyclic peptides with only normal peptide bonds in the ring
-
- 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
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/02—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length in solution
-
- 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
- C07K5/0802—Tripeptides with the first amino acid being neutral
-
- 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
- C07K5/0806—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atoms, i.e. Gly, Ala
-
- 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)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Virology (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Analytical Chemistry (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US19460700P | 2000-04-05 | 2000-04-05 | |
| US60/194,607 | 2000-04-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2002129564A true RU2002129564A (ru) | 2004-05-10 |
Family
ID=22718227
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2002129564/04A RU2002129564A (ru) | 2000-04-05 | 2001-04-03 | Макроциклические ингибиторы сериновой ns3-протеазы, включающие n-циклические р2 структурные элементы вируса гепатита с |
Country Status (26)
Families Citing this family (152)
| 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 |
| US7244721B2 (en) * | 2000-07-21 | 2007-07-17 | Schering Corporation | Peptides as NS3-serine protease inhibitors of hepatitis C virus |
| SV2003000617A (es) * | 2000-08-31 | 2003-01-13 | Lilly Co Eli | Inhibidores de la proteasa peptidomimetica ref. x-14912m |
| US7119072B2 (en) | 2002-01-30 | 2006-10-10 | Boehringer Ingelheim (Canada) Ltd. | Macrocyclic peptides active against the hepatitis C virus |
| US6642204B2 (en) | 2002-02-01 | 2003-11-04 | Boehringer Ingelheim International Gmbh | Hepatitis C inhibitor tri-peptides |
| US7091184B2 (en) | 2002-02-01 | 2006-08-15 | Boehringer Ingelheim International Gmbh | Hepatitis C inhibitor tri-peptides |
| WO2003074478A1 (en) | 2002-03-05 | 2003-09-12 | Sumitomo Chemical Company, Limited | Process for the preparation of biaryl compounds |
| 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 |
| CA2528375C (en) | 2003-06-18 | 2013-11-19 | Tranzyme Pharma, Inc. | Macrocyclic antagonists of the motilin receptor |
| EP1664090A2 (en) | 2003-08-26 | 2006-06-07 | Schering Corporation | Novel peptidomimetic ns3-serine protease inhibitors of hepatitis c virus |
| 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 |
| WO2005043118A2 (en) | 2003-10-27 | 2005-05-12 | Vertex Pharmaceuticals Incorporated | Drug discovery method |
| EP1944042A1 (en) | 2003-10-27 | 2008-07-16 | Vertex Pharmceuticals Incorporated | Combinations for HCV treatment |
| WO2005051980A1 (en) | 2003-11-20 | 2005-06-09 | Schering Corporation | Depeptidized inhibitors of hepatitis c virus ns3 protease |
| WO2005070955A1 (en) | 2004-01-21 | 2005-08-04 | Boehringer Ingelheim International Gmbh | Macrocyclic peptides active against the hepatitis c virus |
| HRP20100048T1 (hr) * | 2004-01-30 | 2010-04-30 | Medivir Ab | Inhibitori hcv ns-3 serin proteaze |
| EP1711515A2 (en) | 2004-02-04 | 2006-10-18 | Vertex Pharmaceuticals Incorporated | Inhibitors of serine proteases, particularly hcv ns3-ns4a protease |
| US20070049593A1 (en) | 2004-02-24 | 2007-03-01 | Japan Tobacco Inc. | Tetracyclic fused heterocyclic compound and use thereof as HCV polymerase inhibitor |
| PT1719773E (pt) | 2004-02-24 | 2009-06-03 | Japan Tobacco Inc | Compostos heterotetracíclicos fundidos e a sua utilização como inibidores da polimerase do hcv |
| 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 |
| US7816326B2 (en) | 2004-02-27 | 2010-10-19 | Schering Corporation | Sulfur compounds as inhibitors of hepatitis C virus NS3 serine protease |
| 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 |
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- 2001-04-03 AU AU2001253124A patent/AU2001253124A1/en not_active Abandoned
- 2001-04-03 EP EP01926601A patent/EP1268525B1/en not_active Expired - Lifetime
- 2001-04-03 NZ NZ521455A patent/NZ521455A/en unknown
- 2001-04-04 EC EC2001004009A patent/ECSP014009A/es unknown
- 2001-04-04 PE PE2001000316A patent/PE20020188A1/es not_active Application Discontinuation
-
2002
- 2002-09-30 ZA ZA200207845A patent/ZA200207845B/en unknown
- 2002-10-04 NO NO20024797A patent/NO20024797L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| JP2003530401A (ja) | 2003-10-14 |
| US6846802B2 (en) | 2005-01-25 |
| US20020107181A1 (en) | 2002-08-08 |
| ES2317900T3 (es) | 2009-05-01 |
| ZA200207845B (en) | 2004-02-11 |
| CN1441806A (zh) | 2003-09-10 |
| MXPA02009920A (es) | 2003-03-27 |
| BR0109861A (pt) | 2003-06-10 |
| AU2001253124A1 (en) | 2001-10-23 |
| PE20020188A1 (es) | 2002-03-13 |
| EP1268525A2 (en) | 2003-01-02 |
| WO2001077113A3 (en) | 2002-06-20 |
| CA2405521C (en) | 2010-06-29 |
| PL359359A1 (en) | 2004-08-23 |
| IL151934A0 (en) | 2003-04-10 |
| ECSP014009A (es) | 2003-03-31 |
| JP4748911B2 (ja) | 2011-08-17 |
| SK14192002A3 (sk) | 2003-03-04 |
| CZ20023321A3 (cs) | 2003-01-15 |
| AR029903A1 (es) | 2003-07-23 |
| WO2001077113A2 (en) | 2001-10-18 |
| ATE419270T1 (de) | 2009-01-15 |
| HK1047947A1 (zh) | 2003-03-14 |
| NZ521455A (en) | 2004-06-25 |
| HUP0400456A3 (en) | 2005-09-28 |
| CA2405521A1 (en) | 2001-10-18 |
| NO20024797D0 (no) | 2002-10-04 |
| NO20024797L (no) | 2002-12-04 |
| HUP0400456A2 (hu) | 2004-06-28 |
| DE60137207D1 (de) | 2009-02-12 |
| KR20030036152A (ko) | 2003-05-09 |
| EP1268525B1 (en) | 2008-12-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA94 | Acknowledgement of application withdrawn (non-payment of fees) |
Effective date: 20060118 |