CA2515216A1 - Macrocyclic hepatitis c serine protease inhibitors - Google Patents
Macrocyclic hepatitis c serine protease inhibitors Download PDFInfo
- Publication number
- CA2515216A1 CA2515216A1 CA002515216A CA2515216A CA2515216A1 CA 2515216 A1 CA2515216 A1 CA 2515216A1 CA 002515216 A CA002515216 A CA 002515216A CA 2515216 A CA2515216 A CA 2515216A CA 2515216 A1 CA2515216 A1 CA 2515216A1
- Authority
- CA
- Canada
- Prior art keywords
- substituted
- aryl
- heteroaryl
- group
- heterocycloalkyl
- Prior art date
- 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
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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 64
- 229910052757 nitrogen Inorganic materials 0.000 claims description 59
- 125000005842 heteroatom Chemical group 0.000 claims description 56
- 229910052717 sulfur Inorganic materials 0.000 claims description 56
- 229910052760 oxygen Inorganic materials 0.000 claims description 55
- 125000001424 substituent group Chemical group 0.000 claims description 48
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 43
- 125000003282 alkyl amino group Chemical group 0.000 claims description 39
- 125000006413 ring segment Chemical group 0.000 claims description 38
- 125000001769 aryl amino group Chemical group 0.000 claims description 37
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 35
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 30
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- 125000003545 alkoxy group Chemical group 0.000 claims description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 26
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 26
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 25
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- 239000000546 pharmaceutical excipient Substances 0.000 claims description 17
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 15
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- 239000003937 drug carrier Substances 0.000 claims description 14
- 125000001188 haloalkyl group Chemical group 0.000 claims description 14
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- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 13
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- 125000005128 aryl amino alkyl group Chemical group 0.000 claims description 12
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
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- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 11
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 10
- 230000000269 nucleophilic effect Effects 0.000 claims description 10
- 150000001408 amides Chemical class 0.000 claims description 9
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
- 241000700605 Viruses Species 0.000 claims description 8
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 8
- 125000005240 diheteroarylamino group Chemical group 0.000 claims description 8
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 6
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 6
- 230000003612 virological effect Effects 0.000 claims description 6
- 208000036142 Viral infection Diseases 0.000 claims description 5
- 229940079322 interferon Drugs 0.000 claims description 5
- 125000004001 thioalkyl group Chemical group 0.000 claims description 5
- 230000009385 viral infection Effects 0.000 claims description 5
- 239000004202 carbamide Substances 0.000 claims description 4
- 150000001716 carbazoles Chemical class 0.000 claims description 4
- 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
- 108060004795 Methyltransferase Proteins 0.000 claims description 3
- 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
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 229960000329 ribavirin Drugs 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
- 229930192474 thiophene Natural products 0.000 claims description 3
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical class C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 claims description 2
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical class C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 claims description 2
- 150000000183 1,3-benzoxazoles Chemical class 0.000 claims description 2
- DKYBVKMIZODYKL-UHFFFAOYSA-N 1,3-diazinane Chemical compound C1CNCNC1 DKYBVKMIZODYKL-UHFFFAOYSA-N 0.000 claims description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 2
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 claims description 2
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical class C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims description 2
- GFFGJBXGBJISGV-UHFFFAOYSA-N adenyl group Chemical group N1=CN=C2N=CNC2=C1N GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 claims description 2
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- 125000003368 amide group Chemical group 0.000 claims description 2
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 2
- 229940111121 antirheumatic drug quinolines Drugs 0.000 claims description 2
- 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 claims description 2
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 2
- 125000000259 cinnolinyl group Chemical class N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 2
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- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 2
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- 229940065721 systemic for obstructive airway disease xanthines Drugs 0.000 claims description 2
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- 125000004853 tetrahydropyridinyl group Chemical class N1(CCCC=C1)* 0.000 claims description 2
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- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical class C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 claims description 2
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- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 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)
- Biophysics (AREA)
- Pharmacology & Pharmacy (AREA)
- Genetics & Genomics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Biochemistry (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)
- Communicable Diseases (AREA)
- Oncology (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)
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 (en) | 2003-02-07 | 2004-02-06 | Macrocyclic hepatitis c serine protease inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2515216A1 true CA2515216A1 (en) | 2004-08-26 |
Family
ID=32872697
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002515216A Abandoned CA2515216A1 (en) | 2003-02-07 | 2004-02-06 | Macrocyclic hepatitis c serine protease inhibitors |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP1590442A4 (de) |
| JP (1) | JP2007524576A (de) |
| KR (1) | KR100940619B1 (de) |
| CN (1) | CN1771050A (de) |
| AU (1) | AU2004211637C1 (de) |
| CA (1) | CA2515216A1 (de) |
| WO (1) | WO2004072243A2 (de) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2490272C2 (ru) * | 2008-02-04 | 2013-08-20 | Айденикс Фармасьютикалз, Инк. | Макроциклические ингибиторы серинпротеазы |
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| US7601709B2 (en) | 2003-02-07 | 2009-10-13 | Enanta Pharmaceuticals, Inc. | Macrocyclic hepatitis C serine protease inhibitors |
| US7176208B2 (en) | 2003-04-18 | 2007-02-13 | Enanta Pharmaceuticals, Inc. | Quinoxalinyl macrocyclic hepatitis C serine protease inhibitors |
| WO2004113365A2 (en) * | 2003-06-05 | 2004-12-29 | Enanta Pharmaceuticals, Inc. | Hepatitis c serine protease tri-peptide inhibitors |
| US7273851B2 (en) | 2003-06-05 | 2007-09-25 | Enanta Pharmaceuticals, Inc. | Tri-peptide hepatitis C serine protease inhibitors |
| US7125845B2 (en) | 2003-07-03 | 2006-10-24 | Enanta Pharmaceuticals, Inc. | Aza-peptide macrocyclic hepatitis C serine protease inhibitors |
| JP4525982B2 (ja) * | 2003-09-26 | 2010-08-18 | シェーリング コーポレイション | Ｃ型肝炎ウイルスのｎｓ３セリンプロテアーゼの大環状インヒビター |
| WO2005037860A2 (en) | 2003-10-10 | 2005-04-28 | Vertex Pharmaceuticals Incoporated | Inhibitors of serine proteases, particularly hcv ns3-ns4a protease |
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| EP2658859A4 (de) | 2010-12-30 | 2014-07-30 | Enanta Pharm Inc | Makrocyclische hepatitis-c-serinprotease-hemmer |
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| EP2914614B1 (de) | 2012-11-05 | 2017-08-16 | Bristol-Myers Squibb Company | Inhibitoren des hepatitis-c-virus |
| WO2014137869A1 (en) | 2013-03-07 | 2014-09-12 | Bristol-Myers Squibb Company | Hepatitis c virus inhibitors |
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| BR112015023351A2 (pt) | 2013-03-15 | 2017-07-18 | Achillion Pharmaceuticals Inc | forma cristalina de sovaprevir, composição farmacêutica, e, método para tratar um distúrbio |
| US9085607B2 (en) | 2013-03-15 | 2015-07-21 | Achillion Pharmaceuticals, Inc. | ACH-0142684 sodium salt polymorph, composition including the same, and method of manufacture thereof |
| WO2014145507A1 (en) | 2013-03-15 | 2014-09-18 | Achillion Pharmaceuticals, Inc. | A process for making a 4-amino-4-oxobutanoyl peptide cyclic analogue, an inhibitor of viral replication, and intermediates thereof |
| EP3089757A1 (de) | 2014-01-03 | 2016-11-09 | AbbVie Inc. | Feste antivirale darreichungsformen |
| EP2899207A1 (de) | 2014-01-28 | 2015-07-29 | Amikana.Biologics | Neues Verfahren zum Testen von HCV-Proteasehemmung |
| CN105130916B (zh) * | 2015-09-30 | 2019-03-01 | 江西师范大学 | 一种高效制备nh-1,2,3三唑化合物的方法 |
| TWI832917B (zh) | 2018-11-06 | 2024-02-21 | 美商富曼西公司 | 經取代之甲苯基殺真菌劑 |
| WO2021127273A1 (en) * | 2019-12-20 | 2021-06-24 | Gb004, Inc. | 1 -((6-oxo-1,6-dihydropyridazin-4-yl)methyl)piperazine and 1 -((6-oxo-1,6-dihydropyrimidin-4-yl)methyl)piperazine derivatives as prolyl hydroxylase, hif-1 alpha and pgk modulators for use in treating inflammatory diseases, cancer or infections |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US6867185B2 (en) * | 2001-12-20 | 2005-03-15 | Bristol-Myers Squibb Company | Inhibitors of hepatitis C virus |
-
2004
- 2004-02-06 CA CA002515216A patent/CA2515216A1/en not_active Abandoned
- 2004-02-06 AU AU2004211637A patent/AU2004211637C1/en not_active Ceased
- 2004-02-06 WO PCT/US2004/003479 patent/WO2004072243A2/en not_active Ceased
- 2004-02-06 JP JP2006503381A patent/JP2007524576A/ja active Pending
- 2004-02-06 CN CNA2004800092686A patent/CN1771050A/zh active Pending
- 2004-02-06 EP EP04709020A patent/EP1590442A4/de not_active Withdrawn
- 2004-02-06 KR KR1020057014600A patent/KR100940619B1/ko not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2490272C2 (ru) * | 2008-02-04 | 2013-08-20 | Айденикс Фармасьютикалз, Инк. | Макроциклические ингибиторы серинпротеазы |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20050111585A (ko) | 2005-11-25 |
| AU2004211637A1 (en) | 2004-08-26 |
| EP1590442A4 (de) | 2007-07-18 |
| AU2004211637C1 (en) | 2010-08-19 |
| WO2004072243A3 (en) | 2005-11-03 |
| AU2004211637B2 (en) | 2009-08-13 |
| JP2007524576A (ja) | 2007-08-30 |
| WO2004072243A2 (en) | 2004-08-26 |
| EP1590442A2 (de) | 2005-11-02 |
| KR100940619B1 (ko) | 2010-02-05 |
| CN1771050A (zh) | 2006-05-10 |
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