NO332056B1 - Hepatitt C inhibitor-forbindelser, farmasoytisk preparat inneholdende slike samt slike forbindelser for behandling av sykdom - Google Patents

Hepatitt C inhibitor-forbindelser, farmasoytisk preparat inneholdende slike samt slike forbindelser for behandling av sykdom Download PDF

Info

Publication number: NO332056B1
Authority: NO; Norway
Prior art keywords: alkyl; cycloalkyl; compound according; mmol; substituted
Prior art date: 2003-05-21

Application number

NO20056047A

Other languages

English (en)

Norwegian (no)

Other versions

NO20056047L (no

Inventor

Montse Llinas-Brunet

Jean Rancourt

Teddy Halmos

Sylvie Goulet

Vida J Gorys

Murray D Bailey

Elise Ghiro

Punit Bhardwaj

Josee Bordeleau

Pasquale Forgione

Nathalie Goudreau

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.)

2003-05-21

Filing date

2005-12-19

Publication date

2012-06-11

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=33476973&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=NO332056(B1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2005-12-19 Application filed by Boehringer Ingelheim Int filed Critical Boehringer Ingelheim Int

2006-01-31 Publication of NO20056047L publication Critical patent/NO20056047L/no

2012-06-11 Publication of NO332056B1 publication Critical patent/NO332056B1/no

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 203
239000003112 inhibitor Substances 0.000 title claims abstract description 59
238000011282 treatment Methods 0.000 title claims abstract description 17
208000005176 Hepatitis C Diseases 0.000 title claims abstract description 14
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title description 10
201000010099 disease Diseases 0.000 title description 9
239000008194 pharmaceutical composition Substances 0.000 title 1
101800001838 Serine protease/helicase NS3 Proteins 0.000 claims abstract description 25
208000036142 Viral infection Diseases 0.000 claims abstract description 6
230000009385 viral infection Effects 0.000 claims abstract description 6
125000000217 alkyl group Chemical group 0.000 claims description 122
239000000203 mixture Substances 0.000 claims description 98
125000000753 cycloalkyl group Chemical group 0.000 claims description 89
-1 3 ,3,3-trifluoropropyl Chemical group 0.000 claims description 60
239000003795 chemical substances by application Substances 0.000 claims description 45
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 41
150000002148 esters Chemical class 0.000 claims description 33
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 30
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 30
150000003839 salts Chemical class 0.000 claims description 30
125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 28
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
229910052736 halogen Inorganic materials 0.000 claims description 23
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 22
125000004432 carbon atom Chemical group C* 0.000 claims description 21
125000001424 substituent group Chemical group 0.000 claims description 21
241000124008 Mammalia Species 0.000 claims description 20
150000002367 halogens Chemical group 0.000 claims description 20
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 19
125000001309 chloro group Chemical group Cl* 0.000 claims description 17
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 17
239000003443 antiviral agent Substances 0.000 claims description 16
239000000825 pharmaceutical preparation Substances 0.000 claims description 15
125000001246 bromo group Chemical group Br* 0.000 claims description 13
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 description 13
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 13
229920002554 vinyl polymer Polymers 0.000 claims description 13
108020004684 Internal Ribosome Entry Sites Proteins 0.000 claims description 11
239000000460 chlorine Substances 0.000 claims description 11
108091005804 Peptidases Proteins 0.000 claims description 9
239000004365 Protease Substances 0.000 claims description 9
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 9
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 claims description 8
125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 8
125000004430 oxygen atom Chemical group O* 0.000 claims description 8
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 7
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 7
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 7
125000005919 1,2,2-trimethylpropyl group Chemical group 0.000 claims description 6
125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
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 6
229910052794 bromium Chemical group 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 6
239000011737 fluorine Substances 0.000 claims description 6
229910052731 fluorine Inorganic materials 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
230000002519 immonomodulatory effect Effects 0.000 claims description 6
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
230000002265 prevention Effects 0.000 claims description 6
229960000329 ribavirin Drugs 0.000 claims description 6
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 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
108060004795 Methyltransferase Proteins 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 4
125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 4
108010047761 Interferon-alpha Proteins 0.000 claims description 4
102000006992 Interferon-alpha Human genes 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims description 4
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
125000004122 cyclic group Chemical group 0.000 claims description 3
125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 3
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 3
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
239000002955 immunomodulating agent Substances 0.000 claims description 2
230000003287 optical effect Effects 0.000 claims description 2
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 164
239000000243 solution Substances 0.000 description 138
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 100
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 90
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 90
229910001868 water Inorganic materials 0.000 description 87
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 85
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 79
239000007787 solid Substances 0.000 description 77
235000019439 ethyl acetate Nutrition 0.000 description 76
239000011541 reaction mixture Substances 0.000 description 76
230000015572 biosynthetic process Effects 0.000 description 63
241000711549 Hepacivirus C Species 0.000 description 59
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 56
238000003786 synthesis reaction Methods 0.000 description 51
238000004007 reversed phase HPLC Methods 0.000 description 50
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 49
238000005481 NMR spectroscopy Methods 0.000 description 48
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 47
238000006243 chemical reaction Methods 0.000 description 47
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 45
238000004128 high performance liquid chromatography Methods 0.000 description 43
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 41
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 38
239000000047 product Substances 0.000 description 36
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 30
239000012267 brine Substances 0.000 description 28
238000003818 flash chromatography Methods 0.000 description 26
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 25
108091032973 (ribonucleotides)n+m Proteins 0.000 description 24
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108010050904 Interferons Proteins 0.000 description 24
102000014150 Interferons Human genes 0.000 description 24
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 24
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238000000034 method Methods 0.000 description 24
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 23
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 22
238000010992 reflux Methods 0.000 description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
239000002904 solvent Substances 0.000 description 20
239000000725 suspension Substances 0.000 description 19
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210000004027 cell Anatomy 0.000 description 17
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
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GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 9
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LCJVIYPJPCBWKS-NXPQJCNCSA-N thymosin Chemical compound SC[C@@H](N)C(=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(C)C)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(C)C)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)=O LCJVIYPJPCBWKS-NXPQJCNCSA-N 0.000 description 1
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230000001988 toxicity Effects 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
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230000035897 transcription Effects 0.000 description 1
230000009466 transformation Effects 0.000 description 1
238000011269 treatment regimen Methods 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
229950002819 valtorcitabine Drugs 0.000 description 1
201000001862 viral hepatitis Diseases 0.000 description 1
230000008957 viral persistence Effects 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- 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
- 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
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- A61K38/19—Cytokines; Lymphokines; Interferons
- A61K38/21—Interferons [IFN]
- A61K38/212—IFN-alpha
- 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
- 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
- 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
- C07K5/0827—Tripeptides containing heteroatoms different from O, S, or N
- 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)
Medicinal Chemistry (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Epidemiology (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Molecular Biology (AREA)
Gastroenterology & Hepatology (AREA)
Immunology (AREA)
Biochemistry (AREA)
Biophysics (AREA)
Genetics & Genomics (AREA)
Virology (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Zoology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Peptides Or Proteins (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

NO20056047A 2003-05-21 2005-12-19 Hepatitt C inhibitor-forbindelser, farmasoytisk preparat inneholdende slike samt slike forbindelser for behandling av sykdom NO332056B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US47270903P	2003-05-21	2003-05-21
PCT/CA2004/000750 WO2004103996A1 (fr)	2003-05-21	2004-05-19	Composes inhibiteurs de l'hepatite c

Publications (2)

Publication Number	Publication Date
NO20056047L NO20056047L (no)	2006-01-31
NO332056B1 true NO332056B1 (no)	2012-06-11

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ID=33476973

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Application Number	Title	Priority Date	Filing Date
NO20056047A NO332056B1 (no)	2003-05-21	2005-12-19	Hepatitt C inhibitor-forbindelser, farmasoytisk preparat inneholdende slike samt slike forbindelser for behandling av sykdom

Country Status (33)

Country	Link
US (5)	US7585845B2 (fr)
EP (1)	EP1654261B1 (fr)
JP (2)	JP4447603B2 (fr)
KR (1)	KR101115294B1 (fr)
CN (3)	CN1791599A (fr)
AT (1)	ATE378334T1 (fr)
AU (1)	AU2004240704B9 (fr)
BR (1)	BRPI0410456B8 (fr)
CA (1)	CA2522577C (fr)
CL (1)	CL2004001161A1 (fr)
CO (1)	CO5630024A2 (fr)
CY (1)	CY1107200T1 (fr)
DE (1)	DE602004010137T2 (fr)
DK (1)	DK1654261T3 (fr)
EA (1)	EA009295B1 (fr)
EC (1)	ECSP056181A (fr)
ES (1)	ES2297424T3 (fr)
HR (1)	HRP20080014T3 (fr)
IL (1)	IL172013A (fr)
ME (1)	MEP58308A (fr)
MX (1)	MXPA05012545A (fr)
MY (1)	MY143076A (fr)
NO (1)	NO332056B1 (fr)
NZ (1)	NZ544076A (fr)
PE (1)	PE20050204A1 (fr)
PL (1)	PL1654261T3 (fr)
PT (1)	PT1654261E (fr)
RS (1)	RS51294B (fr)
TW (1)	TWI327145B (fr)
UA (1)	UA83046C2 (fr)
UY (1)	UY28323A1 (fr)
WO (1)	WO2004103996A1 (fr)
ZA (1)	ZA200508201B (fr)

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KR20080036598A (ko)	2005-08-01	2008-04-28	머크 앤드 캄파니 인코포레이티드	Ｈｃｖｎｓ３ 프로테아제 억제제로서의 마크로사이클릭펩티드
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WO2007109080A2 (fr)	2006-03-16	2007-09-27	Vertex Pharmaceuticals Incorporated	Inhibiteurs de protéase de l'hépatite c deutérés
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2004
- 2004-05-19 HR HR20080014T patent/HRP20080014T3/xx unknown
- 2004-05-19 PE PE2004000512A patent/PE20050204A1/es active IP Right Grant
- 2004-05-19 CN CNA2004800137831A patent/CN1791599A/zh active Pending
- 2004-05-19 JP JP2006529495A patent/JP4447603B2/ja not_active Expired - Fee Related
- 2004-05-19 CN CN201310097223XA patent/CN103203010A/zh active Pending
- 2004-05-19 WO PCT/CA2004/000750 patent/WO2004103996A1/fr not_active Ceased
- 2004-05-19 RS YUP-2005/0871A patent/RS51294B/sr unknown
- 2004-05-19 PT PT04733750T patent/PT1654261E/pt unknown
- 2004-05-19 MY MYPI20041902A patent/MY143076A/en unknown
- 2004-05-19 UY UY28323A patent/UY28323A1/es not_active Application Discontinuation
- 2004-05-19 ES ES04733750T patent/ES2297424T3/es not_active Expired - Lifetime
- 2004-05-19 DE DE602004010137T patent/DE602004010137T2/de not_active Expired - Lifetime
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- 2004-05-19 KR KR1020057022088A patent/KR101115294B1/ko not_active Expired - Fee Related
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- 2004-05-19 DK DK04733750T patent/DK1654261T3/da active
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- 2004-05-19 CA CA2522577A patent/CA2522577C/fr not_active Expired - Fee Related
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- 2004-05-19 CN CN2013100935669A patent/CN103204903A/zh active Pending
- 2004-05-19 CL CL200401161A patent/CL2004001161A1/es unknown
- 2004-05-20 US US10/850,101 patent/US7585845B2/en not_active Expired - Lifetime
- 2004-05-20 TW TW093114272A patent/TWI327145B/zh not_active IP Right Cessation
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2007
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2009
- 2009-11-24 JP JP2009266291A patent/JP2010043129A/ja not_active Withdrawn
2011
- 2011-04-01 US US13/078,225 patent/US8067438B2/en not_active Expired - Lifetime
- 2011-10-21 US US13/278,532 patent/US20120034187A1/en not_active Abandoned
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Also Published As

Publication number	Publication date
AU2004240704A1 (en)	2004-12-02
DE602004010137T2 (de)	2008-09-11
EP1654261B1 (fr)	2007-11-14
ME00382B (me)	2011-05-10
JP2006528937A (ja)	2006-12-28
US20120034187A1 (en)	2012-02-09
DK1654261T3 (da)	2008-01-14
ATE378334T1 (de)	2007-11-15
US20050020503A1 (en)	2005-01-27
US20120269769A1 (en)	2012-10-25
AU2004240704B2 (en)	2009-08-20
US7585845B2 (en)	2009-09-08
CN103204903A (zh)	2013-07-17
CL2004001161A1 (es)	2005-04-08
US7939667B2 (en)	2011-05-10
EA009295B1 (ru)	2007-12-28
WO2004103996A1 (fr)	2004-12-02
TW200508220A (en)	2005-03-01
NZ544076A (en)	2009-04-30
PL1654261T3 (pl)	2008-04-30
PE20050204A1 (es)	2005-05-04
KR20060013671A (ko)	2006-02-13
EP1654261A1 (fr)	2006-05-10
ECSP056181A (es)	2006-04-19
NO20056047L (no)	2006-01-31
AU2004240704B9 (en)	2009-10-22
MXPA05012545A (es)	2006-02-08
ES2297424T3 (es)	2008-05-01
BRPI0410456B1 (pt)	2019-07-09
CA2522577A1 (fr)	2004-12-02
HRP20080014T3 (en)	2008-02-29
MY143076A (en)	2011-02-28
UY28323A1 (es)	2004-12-31
CA2522577C (fr)	2011-04-26
CO5630024A2 (es)	2006-04-28
US20110177030A1 (en)	2011-07-21
IL172013A (en)	2011-10-31
PT1654261E (pt)	2008-01-18
BRPI0410456A (pt)	2006-06-06
JP4447603B2 (ja)	2010-04-07
KR101115294B1 (ko)	2012-04-12
MEP58308A (en)	2011-05-10
RS20050871A (sr)	2007-08-03
TWI327145B (en)	2010-07-11
UA83046C2 (ru)	2008-06-10
EA200501689A1 (ru)	2006-06-30
JP2010043129A (ja)	2010-02-25
US8067438B2 (en)	2011-11-29
CY1107200T1 (el)	2012-11-21
BRPI0410456B8 (pt)	2021-05-25
US20070243166A1 (en)	2007-10-18
CN1791599A (zh)	2006-06-21
CN103203010A (zh)	2013-07-17
ZA200508201B (en)	2007-02-28
DE602004010137D1 (de)	2007-12-27
RS51294B (sr)	2010-12-31

Legal Events

Date	Code	Title	Description
2021-12-27	MM1K	Lapsed by not paying the annual fees

Publication	Publication Date	Title
US7939667B2 (en)	2011-05-10	Hepatitis C inhibitor compounds
TWI274056B (en)	2007-02-21	Hepatitis C inhibitor compound
US7091184B2 (en)	2006-08-15	Hepatitis C inhibitor tri-peptides
US7642235B2 (en)	2010-01-05	Macrocyclic peptides active against the hepatitis C virus
US6919423B2 (en)	2005-07-19	Hepatitis C inhibitor compound
JP4040578B2 (ja)	2008-01-30	Ｃ型肝炎ウイルスに対して活性な大環状ペプチド
CA2474031C (fr)	2010-08-24	Tripeptides heterocycliques utiles en tant qu'inhibiteurs de l'hepatite c
HK1183314A (en)	2013-12-20	Hepatitis c inhibitor compounds
HK1183237A (en)	2013-12-20	Pharmaceutical composition comprising hepatitis c inhibitor compounds