CA2515216A1 - Inhibiteurs macrocycliques de la serine protease de l'hepatite c - Google Patents

Inhibiteurs macrocycliques de la serine protease de l'hepatite c Download PDF

Info

Publication number: CA2515216A1
Authority: CA; Canada
Prior art keywords: substituted; aryl; heteroaryl; group; heterocycloalkyl
Prior art date: 2003-02-07
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

Application number

CA002515216A

Other languages

English (en)

Inventor

Zenwei Miao

Ying Sun

Frank Wu

Suanne Nakajima

Guoyou Xu

Yat Sun Or

Zhe Wang

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Enanta Pharmaceuticals Inc

Original Assignee

Individual

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.)

2003-02-07

Filing date

2004-02-06

Publication date

2004-08-26

2003-03-07 Priority claimed from US10/384,120 external-priority patent/US20040180815A1/en

2004-02-06 Application filed by Individual filed Critical Individual

2004-08-26 Publication of CA2515216A1 publication Critical patent/CA2515216A1/fr

Status Abandoned legal-status Critical Current

Links

208000006454 hepatitis Diseases 0.000 title description 3
231100000283 hepatitis Toxicity 0.000 title description 3
239000003001 serine protease inhibitor Substances 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 442
238000000034 method Methods 0.000 claims abstract description 232
150000003839 salts Chemical class 0.000 claims abstract description 35
241000711549 Hepacivirus C Species 0.000 claims abstract description 32
150000002148 esters Chemical class 0.000 claims abstract description 26
239000000651 prodrug Substances 0.000 claims abstract description 22
229940002612 prodrug Drugs 0.000 claims abstract description 22
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 13
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
125000001072 heteroaryl group Chemical group 0.000 claims description 354
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 245
-1 C3-C12 cycloalkyl Chemical group 0.000 claims description 240
229910052739 hydrogen Inorganic materials 0.000 claims description 237
125000003710 aryl alkyl group Chemical group 0.000 claims description 215
125000003118 aryl group Chemical group 0.000 claims description 211
125000004446 heteroarylalkyl group Chemical group 0.000 claims description 202
239000001257 hydrogen Substances 0.000 claims description 158
125000003107 substituted aryl group Chemical group 0.000 claims description 158
125000000217 alkyl group Chemical group 0.000 claims description 113
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 112
125000000753 cycloalkyl group Chemical group 0.000 claims description 107
229910052736 halogen Inorganic materials 0.000 claims description 95
150000002367 halogens Chemical class 0.000 claims description 94
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 92
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 76
125000004122 cyclic group Chemical group 0.000 claims description 71
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229940079322 interferon Drugs 0.000 claims description 5
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125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 4
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230000010076 replication Effects 0.000 claims description 4
CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical class C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 claims description 3
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IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound 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 description 3
101800001838 Serine protease/helicase NS3 Proteins 0.000 claims description 3
125000000000 cycloalkoxy group Chemical group 0.000 claims description 3
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125000000259 cinnolinyl group Chemical class N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 2
150000001907 coumarones Chemical class 0.000 claims description 2
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150000002012 dioxanes Chemical class 0.000 claims description 2
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UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical class O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 claims description 2
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125000001113 thiadiazolyl group Chemical group 0.000 description 1
AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 1
125000001984 thiazolidinyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
125000004035 thiopropyl group Chemical group [H]SC([H])([H])C([H])([H])C([H])([H])* 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
230000000699 topical effect Effects 0.000 description 1
238000002054 transplantation Methods 0.000 description 1
125000006168 tricyclic group Chemical group 0.000 description 1
WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 1
ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical class CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
235000019871 vegetable fat Nutrition 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
230000029812 viral genome replication Effects 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
239000011787 zinc oxide Substances 0.000 description 1
235000014692 zinc oxide Nutrition 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
- C07K5/12—Cyclic peptides with only normal peptide bonds in the ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- 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
- A61K38/12—Cyclic peptides, e.g. bacitracins; Polymyxins; Gramicidins S, C; Tyrocidins A, B or C
- 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
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
- 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
- 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)
Proteomics, Peptides & Aminoacids (AREA)
Biochemistry (AREA)
Genetics & Genomics (AREA)
Biophysics (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Virology (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Gastroenterology & Hepatology (AREA)
Immunology (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Peptides Or Proteins (AREA)

CA002515216A 2003-02-07 2004-02-06 Inhibiteurs macrocycliques de la serine protease de l'hepatite c Abandoned CA2515216A1 (fr)

Applications Claiming Priority (7)

Application Number	Priority Date	Filing Date	Title
US36094703A	2003-02-07	2003-02-07
US10/360,947		2003-02-07
US36585403A	2003-02-13	2003-02-13
US10/365,854		2003-02-13
US10/384,120		2003-03-07
US10/384,120 US20040180815A1 (en)	2003-03-07	2003-03-07	Pyridazinonyl macrocyclic hepatitis C serine protease inhibitors
PCT/US2004/003479 WO2004072243A2 (fr)	2003-02-07	2004-02-06	Inhibiteurs macrocycliques de la serine protease de l'hepatite c

Publications (1)

Publication Number	Publication Date
CA2515216A1 true CA2515216A1 (fr)	2004-08-26

Family

ID=32872697

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002515216A Abandoned CA2515216A1 (fr)	2003-02-07	2004-02-06	Inhibiteurs macrocycliques de la serine protease de l'hepatite c

Country Status (7)

Country	Link
EP (1)	EP1590442A4 (fr)
JP (1)	JP2007524576A (fr)
KR (1)	KR100940619B1 (fr)
CN (1)	CN1771050A (fr)
AU (1)	AU2004211637C1 (fr)
CA (1)	CA2515216A1 (fr)
WO (1)	WO2004072243A2 (fr)

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KR20160005686A (ko)	2013-03-15	2016-01-15	아칠리온 파르마세우티칼스 인코포레이티드	소바프레비르 다형체들 및 이의 제조 방법
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2004
- 2004-02-06 JP JP2006503381A patent/JP2007524576A/ja active Pending
- 2004-02-06 EP EP04709020A patent/EP1590442A4/fr not_active Withdrawn
- 2004-02-06 KR KR1020057014600A patent/KR100940619B1/ko not_active IP Right Cessation
- 2004-02-06 CN CNA2004800092686A patent/CN1771050A/zh active Pending
- 2004-02-06 WO PCT/US2004/003479 patent/WO2004072243A2/fr active Application Filing
- 2004-02-06 AU AU2004211637A patent/AU2004211637C1/en not_active Ceased
- 2004-02-06 CA CA002515216A patent/CA2515216A1/fr not_active Abandoned

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RU2490272C2 (ru) *	2008-02-04	2013-08-20	Айденикс Фармасьютикалз, Инк.	Макроциклические ингибиторы серинпротеазы

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Publication number	Publication date
KR20050111585A (ko)	2005-11-25
KR100940619B1 (ko)	2010-02-05
EP1590442A4 (fr)	2007-07-18
EP1590442A2 (fr)	2005-11-02
JP2007524576A (ja)	2007-08-30
WO2004072243A2 (fr)	2004-08-26
AU2004211637B2 (en)	2009-08-13
AU2004211637C1 (en)	2010-08-19
CN1771050A (zh)	2006-05-10
WO2004072243A3 (fr)	2005-11-03
AU2004211637A1 (en)	2004-08-26

Legal Events

Date	Code	Title	Description
2007-12-12	EEER	Examination request
2012-02-06	FZDE	Discontinued

Publication	Publication Date	Title
CA2515216A1 (fr)	2004-08-26	Inhibiteurs macrocycliques de la serine protease de l'hepatite c
US7601709B2 (en)	2009-10-13	Macrocyclic hepatitis C serine protease inhibitors
US7662779B2 (en)	2010-02-16	Triazolyl macrocyclic hepatitis C serine protease inhibitors
AU2007265157B2 (en)	2013-06-27	Quinoxalinyl macrocyclic hepatitis C virus serine protease inhibitors
ES2476257T3 (es)	2014-07-14	Compuestos que contienen quinoxalina como inhibidores del virus de la hepatitis C
US7718612B2 (en)	2010-05-18	Pyridazinonyl macrocyclic hepatitis C serine protease inhibitors
US20080038225A1 (en)	2008-02-14	Triazolyl acyclic hepatitis c serine protease inhibitors
US20070281884A1 (en)	2007-12-06	Macrocyclic oximyl hepatitis C protease inhibitors
WO2008134398A1 (fr)	2008-11-06	Inhibiteurs oximyle dipeptides de protéase de l'hépatite c
WO2008019303A2 (fr)	2008-02-14	Inhibiteurs de sérine protéases de l'hépatite c macrocycliques de type pyridazinonyle
CA2656816A1 (fr)	2008-02-14	Inhibiteurs de serine proteases de l'hepatite c macrocycliques de type tetrazolyle
WO2008021960A2 (fr)	2008-02-21	Inhibiteurs triazolyle macrocycliques de la sérine protéase de l'hépatite c
US20070281885A1 (en)	2007-12-06	Macrocylic oximyl hepatitis c protease inhibitors
WO2008021956A2 (fr)	2008-02-21	Inhibiteurs d'acylamino-hétéroaryle de la protéase du virus de l'hépatite c
WO2004113365A9 (fr)	2006-03-23	Inhibiteurs de la tripeptide hepatite c serine protease
WO2005010029A1 (fr)	2005-02-03	Inhibiteurs de la serine protease de l'hepatite c macrocycliques aza-peptidiques
WO2008021733A2 (fr)	2008-02-21	Inhibiteurs acycliques tétrazolylés de la sérine protéase de l'hépaptite c
WO2009070692A1 (fr)	2009-06-04	Inhibiteurs de sérine protéase de l'hépatite c macrocycliques, dérivés de la proline, substitués en c5
WO2004113365A2 (fr)	2004-12-29	Inhibiteurs de la tripeptide hepatite c serine protease
JP2011506472A (ja)	2011-03-03	大環状オキシミルｃ型肝炎セリンプロテアーゼ阻害剤
WO2009085978A1 (fr)	2009-07-09	Inhibiteurs de protéase de sérine de virus de l'hépatite c d'oxime carbocyclique couronnés
WO2009117594A1 (fr)	2009-09-24	Composés macrocycliques fluorés en tant qu'inhibiteurs du virus de l'hépatite c
WO2009070689A1 (fr)	2009-06-04	Dérivés de proline bicycliques substitués en c5 en tant qu'inhibiteurs de la protéase ns3 du virus de l'hépatite c
WO2007146695A1 (fr)	2007-12-21	Inhibiteurs oximyle acycliques de protéase de l'hépatite c
EP2245015A1 (fr)	2010-11-03	Tripeptides difluorés en tant qu'inhibiteurs de la sérine protéase du vhc

CA2515216A1 - Inhibiteurs macrocycliques de la serine protease de l'hepatite c - Google Patents

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