UA74546C2 - Macrocyclic peptides having activity relative to hepatitis c virus, a pharmaceutical composition and use of the pharmaceutical composition - Google Patents

Macrocyclic peptides having activity relative to hepatitis c virus, a pharmaceutical composition and use of the pharmaceutical composition Download PDF

Info

Publication number: UA74546C2
Authority: UA; Ukraine
Prior art keywords: compound; formula; compound according; cis; pharmaceutical composition
Prior art date: 1999-04-06

Application number

UA2001117538A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Boehringer Ingelheim Ca Ltd

Priority date (The priority date 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 date listed.)

1999-04-06

Filing date

2000-03-04

Publication date

2006-01-16

2000-03-04 Application filed by Boehringer Ingelheim Ca Ltd filed Critical Boehringer Ingelheim Ca Ltd

2006-01-16 Publication of UA74546C2 publication Critical patent/UA74546C2/uk

Links

241000711549 Hepacivirus C Species 0.000 title claims abstract description 19
239000008194 pharmaceutical composition Substances 0.000 title claims description 43
230000000694 effects Effects 0.000 title claims description 35
108090000765 processed proteins & peptides Proteins 0.000 title description 19
102000004196 processed proteins & peptides Human genes 0.000 title description 10
229920006395 saturated elastomer Polymers 0.000 claims abstract description 38
125000001424 substituent group Chemical group 0.000 claims abstract description 34
150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 25
150000002148 esters Chemical class 0.000 claims abstract description 24
125000005842 heteroatom Chemical group 0.000 claims abstract description 23
229910052799 carbon Inorganic materials 0.000 claims abstract description 22
150000003839 salts Chemical class 0.000 claims abstract description 19
229910052717 sulfur Chemical group 0.000 claims abstract description 18
150000001408 amides Chemical class 0.000 claims abstract description 17
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 17
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 16
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 15
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125000003118 aryl group Chemical group 0.000 claims abstract description 14
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229910052757 nitrogen Inorganic materials 0.000 claims abstract description 10
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 8
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CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 description 1
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RIKMMFOAQPJVMX-UHFFFAOYSA-N fomepizole Chemical compound CC=1C=NNC=1 RIKMMFOAQPJVMX-UHFFFAOYSA-N 0.000 description 1
229960004285 fomepizole Drugs 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
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238000011141 high resolution liquid chromatography Methods 0.000 description 1
HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
230000028996 humoral immune response Effects 0.000 description 1
238000006197 hydroboration reaction Methods 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
239000005457 ice water Substances 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
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210000000987 immune system Anatomy 0.000 description 1
230000002779 inactivation Effects 0.000 description 1
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
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238000007918 intramuscular administration Methods 0.000 description 1
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238000001990 intravenous administration Methods 0.000 description 1
BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 description 1
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CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
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NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 1
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239000011159 matrix material Substances 0.000 description 1
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RPZHFKHTXCZXQV-UHFFFAOYSA-N mercury(I) oxide Inorganic materials O1[Hg][Hg]1 RPZHFKHTXCZXQV-UHFFFAOYSA-N 0.000 description 1
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CEKCJQBZVNIMLD-UHFFFAOYSA-N methyl 2-amino-4-methoxybenzoate Chemical compound COC(=O)C1=CC=C(OC)C=C1N CEKCJQBZVNIMLD-UHFFFAOYSA-N 0.000 description 1
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
AEXITZJSLGALNH-UHFFFAOYSA-N n'-hydroxyethanimidamide Chemical compound CC(N)=NO AEXITZJSLGALNH-UHFFFAOYSA-N 0.000 description 1
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
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230000003000 nontoxic effect Effects 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000002777 nucleoside Substances 0.000 description 1
229940127073 nucleoside analogue Drugs 0.000 description 1
150000003833 nucleoside derivatives Chemical class 0.000 description 1
239000002773 nucleotide Substances 0.000 description 1
125000003729 nucleotide group Chemical group 0.000 description 1
ZEJPMRKECMRICL-UHFFFAOYSA-N o-ethyl 2-amino-2-oxoethanethioate Chemical compound CCOC(=S)C(N)=O ZEJPMRKECMRICL-UHFFFAOYSA-N 0.000 description 1
UXGHWJFURBQKCJ-UHFFFAOYSA-N oct-7-ene-1,2-diol Chemical compound OCC(O)CCCCC=C UXGHWJFURBQKCJ-UHFFFAOYSA-N 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
229960003104 ornithine Drugs 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000011533 pre-incubation Methods 0.000 description 1
238000002953 preparative HPLC Methods 0.000 description 1
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239000000651 prodrug Substances 0.000 description 1
229940002612 prodrug Drugs 0.000 description 1
VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
235000019833 protease Nutrition 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
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238000012107 replication analysis Methods 0.000 description 1
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210000003705 ribosome Anatomy 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
OHRURASPPZQGQM-GCCNXGTGSA-N romidepsin Chemical compound O1C(=O)[C@H](C(C)C)NC(=O)C(=C/C)/NC(=O)[C@H]2CSSCC\C=C\[C@@H]1CC(=O)N[C@H](C(C)C)C(=O)N2 OHRURASPPZQGQM-GCCNXGTGSA-N 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000003001 serine protease inhibitor Substances 0.000 description 1
125000003607 serino group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C(O[H])([H])[H] 0.000 description 1
150000003384 small molecules Chemical class 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
229910000342 sodium bisulfate Inorganic materials 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
238000002415 sodium dodecyl sulfate polyacrylamide gel electrophoresis Methods 0.000 description 1
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235000011152 sodium sulphate Nutrition 0.000 description 1
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229940095064 tartrate Drugs 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
WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
150000007970 thio esters Chemical group 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
125000004035 thiopropyl group Chemical group [H]SC([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000003585 thioureas Chemical class 0.000 description 1
206010043778 thyroiditis Diseases 0.000 description 1
238000001269 time-of-flight mass spectrometry Methods 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
238000004448 titration Methods 0.000 description 1
125000005490 tosylate group Chemical group 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
ZGYICYBLPGRURT-UHFFFAOYSA-N tri(propan-2-yl)silicon Chemical compound CC(C)[Si](C(C)C)C(C)C ZGYICYBLPGRURT-UHFFFAOYSA-N 0.000 description 1
125000005310 triazolidinyl group Chemical class N1(NNCC1)* 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
239000012588 trypsin Substances 0.000 description 1
238000005199 ultracentrifugation Methods 0.000 description 1
JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
229960005486 vaccine Drugs 0.000 description 1
238000003828 vacuum filtration Methods 0.000 description 1
201000001862 viral hepatitis Diseases 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
229910052727 yttrium Inorganic materials 0.000 description 1
DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-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
- C07K5/06139—Dipeptides with the first amino acid being heterocyclic
- 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
- A61P31/04—Antibacterial agents
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA 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
- 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
- C07K5/0821—Tripeptides with the first amino acid being heterocyclic, e.g. His, Pro, Trp
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Molecular Biology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Genetics & Genomics (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Virology (AREA)
Biophysics (AREA)
Biochemistry (AREA)
Engineering & Computer Science (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Bioinformatics & Cheminformatics (AREA)
Biotechnology (AREA)
Gastroenterology & Hepatology (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Peptides Or Proteins (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

UA2001117538A 1999-04-06 2000-03-04 Macrocyclic peptides having activity relative to hepatitis c virus, a pharmaceutical composition and use of the pharmaceutical composition UA74546C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US12801199P	1999-04-06	1999-04-06
PCT/CA2000/000353 WO2000059929A1 (en)	1999-04-06	2000-04-03	Macrocyclic peptides active against the hepatitis c virus

Publications (1)

Publication Number	Publication Date
UA74546C2 true UA74546C2 (en)	2006-01-16

Family

ID=22433155

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA2001117538A UA74546C2 (en)	1999-04-06	2000-03-04	Macrocyclic peptides having activity relative to hepatitis c virus, a pharmaceutical composition and use of the pharmaceutical composition

Country Status (35)

Country	Link
EP (2)	EP1169339B1 (id)
JP (1)	JP3754298B2 (id)
KR (1)	KR100555229B1 (id)
CN (2)	CN1618789A (id)
AR (1)	AR023260A1 (id)
AT (1)	ATE277945T1 (id)
AU (1)	AU778390B2 (id)
BG (1)	BG65356B1 (id)
BR (1)	BR0009599A (id)
CA (1)	CA2367127C (id)
CO (1)	CO5170502A1 (id)
CZ (1)	CZ20013467A3 (id)
DE (1)	DE60014345T2 (id)
DK (1)	DK1169339T3 (id)
EE (1)	EE04816B1 (id)
ES (1)	ES2230084T3 (id)
HK (1)	HK1042714B (id)
HR (1)	HRP20010720A2 (id)
HU (1)	HUP0300121A3 (id)
ID (1)	ID30459A (id)
IL (2)	IL145375A0 (id)
MX (1)	MXPA01010090A (id)
NO (1)	NO20014857L (id)
NZ (1)	NZ515286A (id)
PE (1)	PE20001649A1 (id)
PL (1)	PL350855A1 (id)
PT (1)	PT1169339E (id)
RU (1)	RU2247126C2 (id)
SI (1)	SI1169339T1 (id)
SK (1)	SK14072001A3 (id)
TR (1)	TR200102878T2 (id)
UA (1)	UA74546C2 (id)
WO (1)	WO2000059929A1 (id)
YU (1)	YU70701A (id)
ZA (1)	ZA200107862B (id)

Families Citing this family (254)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
MXPA03000627A (es) *	2000-07-21	2004-07-30	Schering Corp	Nuevos peptidos como inhibidores de proteasa serina-ns3 del virus de la hepatitis c.
SI1355916T1 (sl)	2001-01-22	2007-04-30	Merck & Co Inc	Nukleozidni derivati kot inhibitorji RNA-odvisne RNA virusne polimeraze
US6867185B2 (en) *	2001-12-20	2005-03-15	Bristol-Myers Squibb Company	Inhibitors of hepatitis C virus
CA2369711A1 (en) *	2002-01-30	2003-07-30	Boehringer Ingelheim (Canada) Ltd.	Macrocyclic peptides active against the hepatitis c virus
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
CA2369970A1 (en) *	2002-02-01	2003-08-01	Boehringer Ingelheim (Canada) Ltd.	Hepatitis c inhibitor tri-peptides
US6642204B2 (en)	2002-02-01	2003-11-04	Boehringer Ingelheim International Gmbh	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
JP2005535574A (ja)	2002-04-11	2005-11-24	バーテックス　ファーマシューティカルズ　インコーポレイテッド	セリンプロテアーゼ、特にｈｃｖｎｓ３−ｎｓ４ａプロテアーゼのインヒビター
MY140680A (en)	2002-05-20	2010-01-15	Bristol Myers Squibb Co	Hepatitis c virus inhibitors
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TR200102878T2 (tr)	2002-01-21
HRP20010720A2 (en)	2002-12-31
NZ515286A (en)	2004-02-27
SK14072001A3 (sk)	2002-03-05
WO2000059929A1 (en)	2000-10-12
PE20001649A1 (es)	2001-02-06
NO20014857L (no)	2001-10-31
PT1169339E (pt)	2004-12-31
CN1177861C (zh)	2004-12-01
CO5170502A1 (es)	2002-06-27
KR20010108465A (ko)	2001-12-07
DE60014345D1 (en)	2004-11-04
JP2002542160A (ja)	2002-12-10
AR023260A1 (es)	2002-09-04
ZA200107862B (en)	2004-06-30
DE60014345T2 (de)	2005-02-17
ES2230084T3 (es)	2005-05-01
EP1169339A1 (en)	2002-01-09
BR0009599A (pt)	2002-01-15
CN1618789A (zh)	2005-05-25
KR100555229B1 (ko)	2006-03-03
YU70701A (sh)	2005-07-19
BG105970A (en)	2002-05-31
ATE277945T1 (de)	2004-10-15
SI1169339T1 (en)	2005-02-28
EP1437362A1 (en)	2004-07-14
CN1346365A (zh)	2002-04-24
CA2367127A1 (en)	2000-10-12
HK1042714A1 (en)	2002-08-23
AU778390B2 (en)	2004-12-02
HK1042714B (zh)	2005-04-01
ID30459A (id)	2001-12-06
JP3754298B2 (ja)	2006-03-08
AU3548000A (en)	2000-10-23
HUP0300121A3 (en)	2004-07-28
MXPA01010090A (es)	2002-04-24
CA2367127C (en)	2005-01-18
NO20014857D0 (no)	2001-10-05
HUP0300121A2 (hu)	2003-06-28
CZ20013467A3 (cs)	2002-06-12
EP1169339B1 (en)	2004-09-29
IL145375A0 (en)	2002-06-30
EE04816B1 (et)	2007-04-16
PL350855A1 (en)	2003-02-10
IL145375A (en)	2007-05-15
BG65356B1 (bg)	2008-03-31
EE200100516A (et)	2002-12-16
DK1169339T3 (da)	2005-01-10
RU2247126C2 (ru)	2005-02-27

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