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 PDF

Info

Publication number: UA77758C2
Authority: UA; Ukraine
Prior art keywords: compound; formula; differs; cyclopentyl; tert
Prior art date: 2002-02-01

Application number

UA20040807172A

Other languages

English (en)

Ukrainian (uk)

Inventor

Vida J Gorys

Original Assignee

Boehringer Ingelheim Int

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.)

2002-02-01

Filing date

2003-01-24

Publication date

2007-01-15

2003-01-24 Application filed by Boehringer Ingelheim Int filed Critical Boehringer Ingelheim Int

2007-01-15 Publication of UA77758C2 publication Critical patent/UA77758C2/uk

Links

239000003112 inhibitor Substances 0.000 title claims abstract description 53
-1 hydroxyproline ester Chemical class 0.000 title claims abstract description 17
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108091005804 Peptidases Proteins 0.000 title description 10
208000006454 hepatitis Diseases 0.000 title description 4
231100000283 hepatitis Toxicity 0.000 title description 4
229960002591 hydroxyproline Drugs 0.000 title description 3
SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 title description 2
PMMYEEVYMWASQN-UHFFFAOYSA-N dl-hydroxyproline Natural products OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 title description 2
FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 title description 2
102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 title 1
125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 137
150000003839 salts Chemical class 0.000 claims abstract description 23
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 22
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
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229950001870 spizofurone Drugs 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000010902 straw Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
229950000244 sulfanilic acid Drugs 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
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
229960004559 theobromine Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
150000003585 thioureas Chemical class 0.000 description 1
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
229960004231 thymalfasin Drugs 0.000 description 1
206010043778 thyroiditis Diseases 0.000 description 1
238000004448 titration Methods 0.000 description 1
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
239000012588 trypsin Substances 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
229950002819 valtorcitabine Drugs 0.000 description 1
LVLANIHJQRZTPY-UHFFFAOYSA-N vinyl carbamate Chemical compound NC(=O)OC=C LVLANIHJQRZTPY-UHFFFAOYSA-N 0.000 description 1
201000001862 viral hepatitis Diseases 0.000 description 1
239000000080 wetting agent Substances 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
- C07K5/08—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
- 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
- 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)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
Molecular Biology (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Chemical Kinetics & Catalysis (AREA)
Biochemistry (AREA)
General Chemical & Material Sciences (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)

UA20040807172A 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 UA77758C2 (en)

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)

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2002
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2003
- 2003-01-24 WO PCT/CA2003/000090 patent/WO2003064456A1/en not_active Ceased
- 2003-01-24 BR BR0307408-0A patent/BR0307408A/pt not_active IP Right Cessation
- 2003-01-24 HR HR20040697A patent/HRP20040697A2/hr not_active Application Discontinuation
- 2003-01-24 KR KR10-2004-7011771A patent/KR20040097990A/ko not_active Abandoned
- 2003-01-24 PL PL03371324A patent/PL371324A1/xx not_active Application Discontinuation
- 2003-01-24 EP EP03700744A patent/EP1474441B1/en not_active Expired - Lifetime
- 2003-01-24 DK DK03700744T patent/DK1474441T3/da active
- 2003-01-24 JP JP2003564076A patent/JP4060801B2/ja not_active Expired - Fee Related
- 2003-01-24 AT AT03700744T patent/ATE358137T1/de active
- 2003-01-24 DE DE60312824T patent/DE60312824T2/de not_active Expired - Lifetime
- 2003-01-24 AU AU2003202347A patent/AU2003202347B2/en not_active Ceased
- 2003-01-24 CN CNB038061643A patent/CN100430414C/zh not_active Expired - Fee Related
- 2003-01-24 EA EA200400987A patent/EA007742B1/ru not_active IP Right Cessation
- 2003-01-24 MX MXPA04007515A patent/MXPA04007515A/es active IP Right Grant
- 2003-01-24 ES ES03700744T patent/ES2285085T3/es not_active Expired - Lifetime
- 2003-01-24 UA UA20040807172A patent/UA77758C2/uk unknown
- 2003-01-24 NZ NZ534689A patent/NZ534689A/en not_active IP Right Cessation
- 2003-01-24 RS YU67204A patent/RS67204A/sr 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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- 2004-08-31 NO NO20043643A patent/NO20043643L/no not_active Application Discontinuation
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Also Published As

Publication number	Publication date
ECSP045226A (es)	2004-09-28
AR038383A1 (es)	2005-01-12
EP1474441A1 (en)	2004-11-10
NO20043643L (no)	2004-08-31
NZ534689A (en)	2007-05-31
EA200400987A1 (ru)	2005-02-24
JP2005530688A (ja)	2005-10-13
WO2003064456A1 (en)	2003-08-07
AU2003202347B2 (en)	2008-10-30
EP1474441B1 (en)	2007-03-28
DE60312824D1 (de)	2007-05-10
PL371324A1 (en)	2005-06-13
PE20031012A1 (es)	2004-01-26
RS67204A (sr)	2006-12-15
SA03240005B1 (ar)	2008-04-15
TW200400199A (en)	2004-01-01
IL163130A (en)	2010-06-30
MY127791A (en)	2006-12-29
DK1474441T3 (da)	2007-07-30
KR20040097990A (ko)	2004-11-18
CN1642974A (zh)	2005-07-20
ATE358137T1 (de)	2007-04-15
CO5611113A2 (es)	2006-02-28
ZA200405933B (en)	2005-09-05
HRP20040697A2 (en)	2005-06-30
MXPA04007515A (es)	2005-07-13
UY27636A1 (es)	2003-09-30
JP4060801B2 (ja)	2008-03-12
BR0307408A (pt)	2004-12-28
EA007742B1 (ru)	2006-12-29
DE60312824T2 (de)	2008-03-06
CA2370396A1 (en)	2003-08-01
CN100430414C (zh)	2008-11-05
ES2285085T3 (es)	2007-11-16

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