CA2557301A1 - Groupes cyclobutenedione contenant des composes servant d'inhibiteurs a la serine protease ns3 du virus de l'hepatite c - Google Patents

Groupes cyclobutenedione contenant des composes servant d'inhibiteurs a la serine protease ns3 du virus de l'hepatite c Download PDF

Info

Publication number: CA2557301A1
Authority: CA; Canada
Prior art keywords: compound; group; alkyl; hcv; compounds
Prior art date: 2004-02-27
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

CA002557301A

Other languages

English (en)

Inventor

Stephane L. Bogen

Weidong Pan

Sumei Ruan

F. George Njoroge

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.)

Merck Sharp and Dohme LLC

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.)

2004-02-27

Filing date

2005-02-24

Publication date

2005-09-15

2005-02-24 Application filed by Individual filed Critical Individual

2005-09-15 Publication of CA2557301A1 publication Critical patent/CA2557301A1/fr

Status Abandoned legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 158
239000003112 inhibitor Substances 0.000 title description 22
108010022999 Serine Proteases Proteins 0.000 title description 12
102000012479 Serine Proteases Human genes 0.000 title description 12
RGBVWCQARBEPPW-UHFFFAOYSA-N cyclobut-3-ene-1,2-dione Chemical group O=C1C=CC1=O RGBVWCQARBEPPW-UHFFFAOYSA-N 0.000 title description 3
108700012707 hepatitis C virus NS3 Proteins 0.000 title 1
238000000034 method Methods 0.000 claims abstract description 75
108091005804 Peptidases Proteins 0.000 claims abstract description 27
239000004365 Protease Substances 0.000 claims abstract description 27
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 27
230000002401 inhibitory effect Effects 0.000 claims abstract description 7
102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 claims abstract 8
241000711549 Hepacivirus C Species 0.000 claims description 74
-1 heteroalkenyl Chemical group 0.000 claims description 62
239000000203 mixture Substances 0.000 claims description 58
125000000217 alkyl group Chemical group 0.000 claims description 56
125000003118 aryl group Chemical group 0.000 claims description 34
150000003839 salts Chemical class 0.000 claims description 32
125000000753 cycloalkyl group Chemical group 0.000 claims description 30
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 30
125000001072 heteroaryl group Chemical group 0.000 claims description 27
125000000623 heterocyclic group Chemical group 0.000 claims description 27
108090000765 processed proteins & peptides Proteins 0.000 claims description 21
125000003710 aryl alkyl group Chemical group 0.000 claims description 19
229940079322 interferon Drugs 0.000 claims description 19
229910052760 oxygen Inorganic materials 0.000 claims description 19
239000012453 solvate Substances 0.000 claims description 19
125000000304 alkynyl group Chemical group 0.000 claims description 18
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
150000002148 esters Chemical class 0.000 claims description 17
125000003342 alkenyl group Chemical group 0.000 claims description 16
229910052739 hydrogen Inorganic materials 0.000 claims description 16
238000011282 treatment Methods 0.000 claims description 16
239000003814 drug Substances 0.000 claims description 15
102000004196 processed proteins & peptides Human genes 0.000 claims description 15
229910052717 sulfur Inorganic materials 0.000 claims description 14
108010050904 Interferons Proteins 0.000 claims description 13
102000014150 Interferons Human genes 0.000 claims description 13
229920001184 polypeptide Polymers 0.000 claims description 11
208000005176 Hepatitis C Diseases 0.000 claims description 10
239000004480 active ingredient Substances 0.000 claims description 9
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
230000000694 effects Effects 0.000 claims description 9
125000004404 heteroalkyl group Chemical group 0.000 claims description 9
125000003545 alkoxy group Chemical group 0.000 claims description 7
125000002877 alkyl aryl group Chemical group 0.000 claims description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
125000004446 heteroarylalkyl group Chemical group 0.000 claims description 7
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 description 6
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
125000004414 alkyl thio group Chemical group 0.000 claims description 6
239000003937 drug carrier Substances 0.000 claims description 6
238000012545 processing Methods 0.000 claims description 6
208000024891 symptom Diseases 0.000 claims description 6
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
125000005110 aryl thio group Chemical group 0.000 claims description 5
125000004104 aryloxy group Chemical group 0.000 claims description 5
229910052731 fluorine Inorganic materials 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
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 description 4
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
229960000329 ribavirin Drugs 0.000 claims description 4
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 description 4
125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
101100240520 Caenorhabditis elegans nhr-14 gene Proteins 0.000 claims description 2
229930194542 Keto Natural products 0.000 claims description 2
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 2
125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 2
125000003282 alkyl amino group Chemical group 0.000 claims description 2
125000005422 alkyl sulfonamido group Chemical group 0.000 claims description 2
125000005281 alkyl ureido group Chemical group 0.000 claims description 2
125000003368 amide group Chemical group 0.000 claims description 2
125000001769 aryl amino group Chemical group 0.000 claims description 2
125000005421 aryl sulfonamido group Chemical group 0.000 claims description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
125000005518 carboxamido group Chemical group 0.000 claims description 2
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
125000000468 ketone group Chemical group 0.000 claims description 2
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 2
125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 2
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
239000003443 antiviral agent Substances 0.000 claims 4
125000001475 halogen functional group Chemical group 0.000 claims 2
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 1
230000001747 exhibiting effect Effects 0.000 claims 1
125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
238000007920 subcutaneous administration Methods 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 102
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 99
239000000243 solution Substances 0.000 description 91
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 70
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 55
239000000543 intermediate Substances 0.000 description 52
238000002360 preparation method Methods 0.000 description 52
235000019439 ethyl acetate Nutrition 0.000 description 49
238000006243 chemical reaction Methods 0.000 description 44
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 43
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 41
235000002639 sodium chloride Nutrition 0.000 description 40
239000012044 organic layer Substances 0.000 description 36
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 35
239000011541 reaction mixture Substances 0.000 description 31
229910052943 magnesium sulfate Inorganic materials 0.000 description 29
150000001412 amines Chemical class 0.000 description 28
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
239000012267 brine Substances 0.000 description 26
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 26
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
239000000047 product Substances 0.000 description 24
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
238000000746 purification Methods 0.000 description 21
102100038132 Endogenous retrovirus group K member 6 Pro protein Human genes 0.000 description 20
125000004432 carbon atom Chemical group C* 0.000 description 20
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
239000007787 solid Substances 0.000 description 18
239000000758 substrate Substances 0.000 description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
239000002253 acid Substances 0.000 description 17
229910052799 carbon Inorganic materials 0.000 description 17
239000003921 oil Substances 0.000 description 17
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 16
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 16
101710144111 Non-structural protein 3 Proteins 0.000 description 16
229910052757 nitrogen Inorganic materials 0.000 description 16
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
229910000030 sodium bicarbonate Inorganic materials 0.000 description 14
239000010410 layer Substances 0.000 description 13
230000002829 reductive effect Effects 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 11
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KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
239000000463 material Substances 0.000 description 11
239000000651 prodrug Substances 0.000 description 11
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125000001424 substituent group Chemical group 0.000 description 11
239000007821 HATU Substances 0.000 description 10
230000015572 biosynthetic process Effects 0.000 description 10
IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
125000006413 ring segment Chemical group 0.000 description 10
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 9
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
238000003556 assay Methods 0.000 description 9
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
125000004122 cyclic group Chemical group 0.000 description 9
235000019441 ethanol Nutrition 0.000 description 9
239000001301 oxygen Substances 0.000 description 9
238000010898 silica gel chromatography Methods 0.000 description 9
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
229920002472 Starch Polymers 0.000 description 8
235000001014 amino acid Nutrition 0.000 description 8
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NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 8
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QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 7
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230000003647 oxidation Effects 0.000 description 6
238000007254 oxidation reaction Methods 0.000 description 6
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
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239000011593 sulfur Substances 0.000 description 6
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208000030507 AIDS Diseases 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
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238000005550 wet granulation Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
- 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
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
- 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
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Bioinformatics & Cheminformatics (AREA)
Virology (AREA)
Engineering & Computer Science (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Diabetes (AREA)
Molecular Biology (AREA)
Hematology (AREA)
Obesity (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)

CA002557301A 2004-02-27 2005-02-24 Groupes cyclobutenedione contenant des composes servant d'inhibiteurs a la serine protease ns3 du virus de l'hepatite c Abandoned CA2557301A1 (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US54842304P	2004-02-27	2004-02-27
US60/548,423		2004-02-27
PCT/US2005/006083 WO2005085197A1 (fr)	2004-02-27	2005-02-24	Groupes cyclobutenedione contenant des composes servant d'inhibiteurs a la serine protease ns3 du virus de l'hepatite c

Publications (1)

Publication Number	Publication Date
CA2557301A1 true CA2557301A1 (fr)	2005-09-15

Family

ID=34919362

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002557301A Abandoned CA2557301A1 (fr)	2004-02-27	2005-02-24	Groupes cyclobutenedione contenant des composes servant d'inhibiteurs a la serine protease ns3 du virus de l'hepatite c

Country Status (5)

Country	Link
EP (1)	EP1742914A1 (fr)
JP (1)	JP2007525521A (fr)
CN (1)	CN1946690A (fr)
CA (1)	CA2557301A1 (fr)
WO (1)	WO2005085197A1 (fr)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US20060275366A1 (en) *	2005-06-02	2006-12-07	Schering Corporation	Controlled-release formulation
US20060276407A1 (en) *	2005-06-02	2006-12-07	Schering Corporation	Methods of treating hepatitis C virus
AU2006252623A1 (en) *	2005-06-02	2006-12-07	Schering Corporation	Controlled-release formulation useful for treating disorders associated with hepatitis C virus
US20060276404A1 (en) *	2005-06-02	2006-12-07	Anima Ghosal	Medicaments and methods combining a HCV protease inhibitor and an AKR competitor
US20060276406A1 (en) *	2005-06-02	2006-12-07	Schering Corporation	Methods of treating hepatitis C virus
US20070021351A1 (en) *	2005-06-02	2007-01-25	Schering Corporation	Liver/plasma concentration ratio for dosing hepatitis C virus protease inhibitor
WO2006130626A2 (fr) *	2005-06-02	2006-12-07	Schering Corporation	Procede de modulation de l'activite de la protease du vhc au moyen d'un nouvel inhibiteur de la protease du vhc aux fins de la reduction de la duree du traitement
DK1966130T3 (da)	2005-12-23	2014-02-10	Zealand Pharma As	Modificerede lysin-mimetiske forbindelser
US7816348B2 (en)	2006-02-03	2010-10-19	Boehringer Ingelheim International Gmbh	Viral polymerase inhibitors
CN101506167A (zh)	2006-08-17	2009-08-12	贝林格尔.英格海姆国际有限公司	病毒聚合酶抑制剂
EP2074087A2 (fr)	2006-12-21	2009-07-01	Wyeth	Synthese de composes de pyrrolidine
CA2693997C (fr)	2007-08-03	2013-01-15	Pierre L. Beaulieu	Inhibiteurs de polymerase virale
EP2234977A4 (fr)	2007-12-19	2011-04-13	Boehringer Ingelheim Int	Inhibiteurs de polymérase virale
RU2011127080A (ru)	2009-01-07	2013-02-20	Сайнексис, Инк.	Производное циклоспорина для применения в лечении заражения вирусом гепатита с и вич
CN103387510B (zh) *	2013-08-08	2015-09-09	苏州永健生物医药有限公司	一种β-氨基-alpha-羟基环丁基丁酰胺盐酸盐的合成方法
WO2018202865A1 (fr)	2017-05-05	2018-11-08	Zealand Pharma A/S	Modulateurs de la communication intercellulaire par les jonctions lacunaires et leur utilisation pour le traitement d'une maladie oculaire diabétique

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5168103A (en) *	1991-01-22	1992-12-01	American Home Products Corporation	[[2-(amino-3,4-dioxo-1-cyclobuten-1-yl) amino]alkyl]-acid derivatives
US6323180B1 (en) *	1998-08-10	2001-11-27	Boehringer Ingelheim (Canada) Ltd	Hepatitis C inhibitor tri-peptides
UA74546C2 (en) *	1999-04-06	2006-01-16	Boehringer Ingelheim Ca Ltd	Macrocyclic peptides having activity relative to hepatitis c virus, a pharmaceutical composition and use of the pharmaceutical composition
ATE297946T1 (de) *	2000-04-03	2005-07-15	Vertex Pharma	Inhibitoren von serin proteasen, speziell der hepatitis-c-virus ns3-protease
CZ2003195A3 (cs) *	2000-07-21	2003-04-16	Schering Corporation	Peptidové inhibitory serinové proteázy NS3 a farmaceutický prostředek
US7244721B2 (en) *	2000-07-21	2007-07-17	Schering Corporation	Peptides as NS3-serine protease inhibitors of hepatitis C virus
KR100939155B1 (ko) *	2000-07-21	2010-01-28	쉐링 코포레이션	Ｃ형 간염 바이러스의 ｎｓ3-세린 프로테아제 억제제로서의신규한 펩티드
JP2004530650A (ja) *	2001-02-07	2004-10-07	アボット・ラボラトリーズ	カリウムチャンネル開口薬としてのアミナールジオン
NZ543869A (en) *	2001-04-16	2007-09-28	Schering Corp	3,4-di-substituted cyclobutene-1,2-diones as cxc-chemokine repcetor ligands
US20040106794A1 (en) *	2001-04-16	2004-06-03	Schering Corporation	3,4-Di-substituted cyclobutene-1,2-diones as CXC-chemokine receptor ligands

2005
- 2005-02-24 CA CA002557301A patent/CA2557301A1/fr not_active Abandoned
- 2005-02-24 JP JP2007501006A patent/JP2007525521A/ja active Pending
- 2005-02-24 CN CNA2005800126511A patent/CN1946690A/zh active Pending
- 2005-02-24 WO PCT/US2005/006083 patent/WO2005085197A1/fr active Application Filing
- 2005-02-24 EP EP05723791A patent/EP1742914A1/fr not_active Withdrawn

Also Published As

Publication number	Publication date
CN1946690A (zh)	2007-04-11
JP2007525521A (ja)	2007-09-06
WO2005085197A1 (fr)	2005-09-15
EP1742914A1 (fr)	2007-01-17

Publication	Publication Date	Title
EP1939213B1 (fr)	2010-08-25	Nouveaux composés en tant qu'inhibiteurs de la sérine protéase NS3 du virus de l'hépatite C
EP1737821B1 (fr)	2009-08-05	Composes de proline fusionnes a 3,4-(cyclopentyl) en tant qu'inhibiteurs de la protease serine ns3 du virus de l'hepatite c
US7423058B2 (en)	2008-09-09	Inhibitors of hepatitis C virus NS3 protease
EP1730142B1 (fr)	2011-06-29	Nouveaux cetoamides a p4 cycliques en tant qu'inhibiteurs de la ns3 serine protease du virus de l'hepatite c
EP1773868B1 (fr)	2009-07-15	Prolines substituées en tant qu`inhibiteurs de la sérine protéase du virus ns3 de l`hépatite c
US7635694B2 (en)	2009-12-22	Cyclobutenedione-containing compounds as inhibitors of hepatitis C virus NS3 serine protease
EP1748983A2 (fr)	2007-02-07	Nouveaux composes en tant qu'inhibiteurs de la protease serine ns3 du virus de l'hepatite c
CA2549167A1 (fr)	2005-06-30	Inhibiteurs de la protease serine ns3/ns4a du virus de l'hepatite c (hcv)
WO2005087731A1 (fr)	2005-09-22	Composes soufres en tant qu'inhibiteurs de la protease serine ns3 du virus de l'hepatite c
CA2557301A1 (fr)	2005-09-15	Groupes cyclobutenedione contenant des composes servant d'inhibiteurs a la serine protease ns3 du virus de l'hepatite c
MXPA06009809A (en)	2007-04-10	Cyclobutenedione groups-containing compounds as inhibitors of hepatitis c virus ns3 serine protease
MXPA06009812A (en)	2007-04-10	Novel compounds as inhibitors of hepatitis c virus ns3 serine protease
MXPA06009815A (en)	2007-04-10	3,4-(cyclopentyl)-fused proline compounds as inhibitors of hepatitis c virus ns3 serine protease
MXPA06009811A (en)	2007-04-10	Compounds as inhibitors of hepatitis c virus ns3 serine protease
MXPA06009814A (en)	2007-04-10	Inhibitors of hepatitis c virus ns3 protease
MXPA06009810A (en)	2007-04-10	Novel ketoamides with cyclic p4's as inhibitors of ns3 serine protease of hepatitis c virus

Legal Events

Date	Code	Title	Description
2010-02-16	EEER	Examination request
2013-04-22	FZDE	Dead	Effective date: 20130225