PT1987038E - Inibidores de ns5b de hcv - Google Patents
Inibidores de ns5b de hcv Download PDFInfo
- Publication number
- PT1987038E PT1987038E PT07763294T PT07763294T PT1987038E PT 1987038 E PT1987038 E PT 1987038E PT 07763294 T PT07763294 T PT 07763294T PT 07763294 T PT07763294 T PT 07763294T PT 1987038 E PT1987038 E PT 1987038E
- Authority
- PT
- Portugal
- Prior art keywords
- cyclohexyl
- benzazepine
- carboxylic acid
- methyl
- indolo
- Prior art date
Links
- 239000003112 inhibitor Substances 0.000 title claims description 30
- 101710112514 Host translation inhibitor 5b Proteins 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 88
- 239000000203 mixture Substances 0.000 claims abstract description 47
- -1 N-alkylpiperazinyl Chemical group 0.000 claims description 92
- 229910052739 hydrogen Inorganic materials 0.000 claims description 61
- 150000004702 methyl esters Chemical class 0.000 claims description 44
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- QXPUBANOKZYTQC-UHFFFAOYSA-N C1C=CC=C2C=CN=C12 Chemical compound C1C=CC=C2C=CN=C12 QXPUBANOKZYTQC-UHFFFAOYSA-N 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 10
- OAQBOILMPKLGMA-UHFFFAOYSA-N 13-cyclohexyl-3-methoxy-6-[5-(3-morpholin-4-yl-3-oxopropyl)-1,3-oxazol-2-yl]-6,7-dihydro-5h-indolo[2,1-a][2]benzazepine-10-carboxylic acid Chemical compound C12=CC=C(C(O)=O)C=C2N2CC(C=3OC(CCC(=O)N4CCOCC4)=CN=3)CC3=CC(OC)=CC=C3C2=C1C1CCCCC1 OAQBOILMPKLGMA-UHFFFAOYSA-N 0.000 claims description 9
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 9
- 150000002431 hydrogen Chemical group 0.000 claims description 9
- GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 108700008776 hepatitis C virus NS-5 Proteins 0.000 claims description 7
- 125000002757 morpholinyl group Chemical group 0.000 claims description 6
- 125000004193 piperazinyl group Chemical group 0.000 claims description 6
- 125000003386 piperidinyl group Chemical group 0.000 claims description 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 102000014150 Interferons Human genes 0.000 claims description 5
- 108010050904 Interferons Proteins 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- VHDRZIOZSVZFLW-UHFFFAOYSA-N 13-cyclohexyl-6-(2-oxo-3h-1,3,4-oxadiazol-5-yl)-7h-indolo[2,1-a][2]benzazepine-10-carboxylic acid Chemical compound C=12C3=CC=CC=C3C=C(C=3OC(=O)NN=3)CN2C2=CC(C(=O)O)=CC=C2C=1C1CCCCC1 VHDRZIOZSVZFLW-UHFFFAOYSA-N 0.000 claims description 4
- 108060004795 Methyltransferase Proteins 0.000 claims description 4
- 101800001019 Non-structural protein 4B Proteins 0.000 claims description 4
- 101800001014 Non-structural protein 5A Proteins 0.000 claims description 4
- 230000008901 benefit Effects 0.000 claims description 4
- 229930182912 cyclosporin Natural products 0.000 claims description 4
- 230000010076 replication Effects 0.000 claims description 4
- 239000003001 serine protease inhibitor Substances 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- JENCSXHYAOKYPH-UHFFFAOYSA-N 5h-indole Chemical compound C1C=CC2=NC=CC2=C1 JENCSXHYAOKYPH-UHFFFAOYSA-N 0.000 claims description 3
- JRBOPJICFCXBOU-UHFFFAOYSA-N 6-(5-amino-1,3,4-oxadiazol-2-yl)-13-cyclohexyl-7h-indolo[2,1-a][2]benzazepine-10-carboxylic acid Chemical compound O1C(N)=NN=C1C(CN1C2=CC(=CC=C22)C(O)=O)=CC3=CC=CC=C3C1=C2C1CCCCC1 JRBOPJICFCXBOU-UHFFFAOYSA-N 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims description 2
- AZPJUFRNELUFLN-UHFFFAOYSA-N 13-cyclohexyl-6-(3-methyl-1,2,4-oxadiazol-5-yl)-7h-indolo[2,1-a][2]benzazepine-10-carboxylic acid Chemical compound CC1=NOC(C=2CN3C4=CC(=CC=C4C(C4CCCCC4)=C3C3=CC=CC=C3C=2)C(O)=O)=N1 AZPJUFRNELUFLN-UHFFFAOYSA-N 0.000 claims description 2
- MWAKBTJMEQSBOT-UHFFFAOYSA-N 13-cyclohexyl-6-[5-(3-morpholin-4-yl-3-oxopropyl)-1,3-oxazol-2-yl]-7h-indolo[2,1-a][2]benzazepine-10-carboxylic acid Chemical compound C=12C3=CC=CC=C3C=C(C=3OC(CCC(=O)N4CCOCC4)=CN=3)CN2C2=CC(C(=O)O)=CC=C2C=1C1CCCCC1 MWAKBTJMEQSBOT-UHFFFAOYSA-N 0.000 claims description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000001425 triazolyl group Chemical group 0.000 claims description 2
- 239000012268 protein inhibitor Substances 0.000 claims 5
- 229940121649 protein inhibitor Drugs 0.000 claims 5
- 108010036941 Cyclosporins Proteins 0.000 claims 2
- 229940122750 HCV entry inhibitor Drugs 0.000 claims 2
- 229940124683 HCV polymerase inhibitor Drugs 0.000 claims 2
- 208000005176 Hepatitis C Diseases 0.000 claims 2
- 102000015696 Interleukins Human genes 0.000 claims 2
- 108010063738 Interleukins Proteins 0.000 claims 2
- 208000010710 hepatitis C virus infection Diseases 0.000 claims 2
- 229940047124 interferons Drugs 0.000 claims 2
- 229940047122 interleukins Drugs 0.000 claims 2
- 239000003475 metalloproteinase inhibitor Substances 0.000 claims 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 2
- 230000001225 therapeutic effect Effects 0.000 claims 2
- LHKGCSPKZSEBFS-UHFFFAOYSA-N 13-cyclohexyl-6-[1-(oxan-4-ylmethyl)tetrazol-5-yl]-7h-indolo[2,1-a][2]benzazepine-10-carboxylic acid Chemical compound C=12C3=CC=CC=C3C=C(C=3N(N=NN=3)CC3CCOCC3)CN2C2=CC(C(=O)O)=CC=C2C=1C1CCCCC1 LHKGCSPKZSEBFS-UHFFFAOYSA-N 0.000 claims 1
- MIGPAWNSNSDOEF-UHFFFAOYSA-N 13-cyclohexyl-6-[1-(oxolan-2-ylmethyl)tetrazol-5-yl]-7h-indolo[2,1-a][2]benzazepine-10-carboxylic acid Chemical compound C=12C3=CC=CC=C3C=C(C=3N(N=NN=3)CC3OCCC3)CN2C2=CC(C(=O)O)=CC=C2C=1C1CCCCC1 MIGPAWNSNSDOEF-UHFFFAOYSA-N 0.000 claims 1
- DMCJVDJCLOVVHU-UHFFFAOYSA-N 13-cyclohexyl-6-[2-(2-hydroxyethyl)-1,3-dihydrotetrazol-5-yl]-7h-indolo[2,1-a][2]benzazepine-10-carboxylic acid Chemical compound N1N(CCO)NN=C1C(CN1C2=CC(=CC=C22)C(O)=O)=CC3=CC=CC=C3C1=C2C1CCCCC1 DMCJVDJCLOVVHU-UHFFFAOYSA-N 0.000 claims 1
- FWLGWROWKLGCSG-UHFFFAOYSA-N 13-cyclohexyl-6-[2-(oxan-4-ylmethyl)tetrazol-5-yl]-5h-indolo[2,1-a][2]benzazepine-10-carboxylic acid Chemical compound C=12C3=CC=CC=C3CC(C3=NN(CC4CCOCC4)N=N3)=CN2C2=CC(C(=O)O)=CC=C2C=1C1CCCCC1 FWLGWROWKLGCSG-UHFFFAOYSA-N 0.000 claims 1
- RZICPBVSRPKWNS-UHFFFAOYSA-N 13-cyclohexyl-n-(dimethylsulfamoyl)-3-methoxy-6-(1,3-oxazol-2-yl)-6,7-dihydro-5h-indolo[2,1-a][2]benzazepine-10-carboxamide Chemical compound C12=CC=C(C(=O)NS(=O)(=O)N(C)C)C=C2N2CC(C=3OC=CN=3)CC3=CC(OC)=CC=C3C2=C1C1CCCCC1 RZICPBVSRPKWNS-UHFFFAOYSA-N 0.000 claims 1
- MGGGCCZERFYBEM-UHFFFAOYSA-N 13-cyclohexyl-n-(dimethylsulfamoyl)-6-(3-methyl-1,2,4-oxadiazol-5-yl)-7h-indolo[2,1-a][2]benzazepine-10-carboxamide Chemical compound C=12C3=CC=CC=C3C=C(C=3ON=C(C)N=3)CN2C2=CC(C(=O)NS(=O)(=O)N(C)C)=CC=C2C=1C1CCCCC1 MGGGCCZERFYBEM-UHFFFAOYSA-N 0.000 claims 1
- NWJNBUZBXRSWBO-UHFFFAOYSA-N 13-cyclohexyl-n-(dimethylsulfamoyl)-6-[1-methyl-5-(oxan-4-ylmethyl)-1,2,4-triazol-3-yl]-7h-indolo[2,1-a][2]benzazepine-10-carboxamide Chemical compound C=12C3=CC=CC=C3C=C(C3=NN(C)C(CC4CCOCC4)=N3)CN2C2=CC(C(=O)NS(=O)(=O)N(C)C)=CC=C2C=1C1CCCCC1 NWJNBUZBXRSWBO-UHFFFAOYSA-N 0.000 claims 1
- WFBQIFSWUVAQMF-UHFFFAOYSA-N 6-[5-[(2-bromoacetyl)amino]-1,3,4-oxadiazol-2-yl]-13-cyclohexyl-7h-indolo[2,1-a][2]benzazepine-10-carboxylic acid Chemical compound C=12C3=CC=CC=C3C=C(C=3OC(NC(=O)CBr)=NN=3)CN2C2=CC(C(=O)O)=CC=C2C=1C1CCCCC1 WFBQIFSWUVAQMF-UHFFFAOYSA-N 0.000 claims 1
- 125000000520 N-substituted aminocarbonyl group Chemical group [*]NC(=O)* 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 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 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- 241000711549 Hepacivirus C Species 0.000 abstract description 50
- 238000000034 method Methods 0.000 abstract description 18
- 230000000694 effects Effects 0.000 abstract description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 201
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- 238000006243 chemical reaction Methods 0.000 description 167
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 120
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- 235000019439 ethyl acetate Nutrition 0.000 description 59
- 238000005481 NMR spectroscopy Methods 0.000 description 56
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 48
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- 239000000243 solution Substances 0.000 description 42
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 32
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- FRUWAONHRDGSAL-UHFFFAOYSA-N 7h-indolo[2,1-a][2]benzazepine-10-carboxylic acid Chemical compound C1=CCN2C3=CC(C(=O)O)=CC=C3C=C2C2=CC=CC=C21 FRUWAONHRDGSAL-UHFFFAOYSA-N 0.000 description 13
- 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 description 13
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- 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 description 13
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Classifications
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- 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
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- 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- 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
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- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Hydrogenated Pyridines (AREA)
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| US77139106P | 2006-02-08 | 2006-02-08 |
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| ES (1) | ES2352574T3 (enExample) |
| HR (1) | HRP20100672T1 (enExample) |
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| SI (1) | SI1987038T1 (enExample) |
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| US20070049593A1 (en) | 2004-02-24 | 2007-03-01 | Japan Tobacco Inc. | Tetracyclic fused heterocyclic compound and use thereof as HCV polymerase inhibitor |
| US7659263B2 (en) | 2004-11-12 | 2010-02-09 | Japan Tobacco Inc. | Thienopyrrole compound and use thereof as HCV polymerase inhibitor |
| US7399758B2 (en) * | 2005-09-12 | 2008-07-15 | Meanwell Nicholas A | Cyclopropyl fused indolobenzazepine HCV NS5B inhibitors |
| US7456165B2 (en) | 2006-02-08 | 2008-11-25 | Bristol-Myers Squibb Company | HCV NS5B inhibitors |
| US7521443B2 (en) * | 2006-05-17 | 2009-04-21 | Bristol-Myers Squibb Company | Cyclopropyl fused indolobenzazepine HCV NS5B inhibitors |
| US7456166B2 (en) * | 2006-05-17 | 2008-11-25 | Bristol-Myers Squibb Company | Cyclopropyl fused indolobenzazepine HCV NS5B inhibitors |
| US7521441B2 (en) * | 2006-05-22 | 2009-04-21 | Bristol-Myers Squibb Company | Cyclopropyl fused indolobenzazepine HCV NS5B inhibitors |
| ATE469155T1 (de) * | 2006-05-25 | 2010-06-15 | Bristol Myers Squibb Co | Cyclopropyl-fusionierte indolbenzazepin-hcv-ns5b- hemmer |
| WO2007140200A2 (en) * | 2006-05-25 | 2007-12-06 | Bristol-Myers Squibb Company | Cyclopropyl fused indolobenzazepine hcv ns5b inhibitors |
| US7452876B2 (en) * | 2006-06-08 | 2008-11-18 | Bristol-Myers Squibb Company | Cyclopropyl fused indolobenzazepine HCV NS5B inhibitors |
| US7541351B2 (en) * | 2007-01-11 | 2009-06-02 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| US7541352B2 (en) * | 2007-02-02 | 2009-06-02 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| US7517872B2 (en) * | 2007-02-22 | 2009-04-14 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| US7998951B2 (en) * | 2007-03-05 | 2011-08-16 | Bristol-Myers Squibb Company | HCV NS5B inhibitors |
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| US8143243B2 (en) * | 2007-08-09 | 2012-03-27 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| US7642251B2 (en) * | 2007-08-09 | 2010-01-05 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| US8124601B2 (en) | 2007-11-21 | 2012-02-28 | Bristol-Myers Squibb Company | Compounds for the treatment of Hepatitis C |
| US8129367B2 (en) * | 2007-11-21 | 2012-03-06 | Bristol-Myers Squibb Company | Compounds for the treatment of Hepatitis C |
| BRPI0821342A2 (pt) | 2007-12-19 | 2019-09-24 | Boehringer Ingelheim Int | inibidores da polimerase viral |
| WO2009120733A1 (en) * | 2008-03-27 | 2009-10-01 | Bristol-Myers Squibb Company | Pyrrolidine fused indolobenzadiazepine hcv ns5b inhibitors |
| JP2011515496A (ja) * | 2008-03-27 | 2011-05-19 | ブリストル−マイヤーズ スクイブ カンパニー | ジオキソランおよびジオキソラノン縮合インドロベンザジアゼピンｈｃｖｎｓ５ｂ阻害剤 |
| CN101977914A (zh) * | 2008-03-27 | 2011-02-16 | 百时美施贵宝公司 | 用于治疗丙型肝炎的化合物 |
| KR20100124848A (ko) | 2008-03-27 | 2010-11-29 | 브리스톨-마이어스 스큅 컴퍼니 | 방향족 헤테로시클릭 융합된 인돌로벤자디아제핀 ｈｃｖ ｎｓ5ｂ 억제제 |
| US8133884B2 (en) * | 2008-05-06 | 2012-03-13 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| UY32099A (es) | 2008-09-11 | 2010-04-30 | Enanta Pharm Inc | Inhibidores macrocíclicos de serina proteasas de hepatitis c |
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| JP2012517468A (ja) * | 2009-02-11 | 2012-08-02 | ブリストル−マイヤーズ スクイブ カンパニー | Ｃ型肝炎治療のための化合物 |
| US8143244B2 (en) * | 2009-02-26 | 2012-03-27 | Bristol-Myers Squibb Company | Cyclopropyl fused indolobenzazepine HCV NS5B inhibitors |
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| US10201584B1 (en) | 2011-05-17 | 2019-02-12 | Abbvie Inc. | Compositions and methods for treating HCV |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US20040138109A1 (en) * | 2002-09-30 | 2004-07-15 | Boehringer Ingelheim Pharmaceuticals, Inc. | Potent inhibitor of HCV serine protease |
| JP2006526011A (ja) * | 2003-04-11 | 2006-11-16 | バーテックス ファーマシューティカルズ インコーポレイテッド | セリンプロテアーゼ（特に、ｈｃｖｎｓ３−ｎｓ４ａプロテアーゼ）のインヒビター |
| US20050119318A1 (en) * | 2003-10-31 | 2005-06-02 | Hudyma Thomas W. | Inhibitors of HCV replication |
| EP1719773B1 (en) | 2004-02-24 | 2009-04-15 | Japan Tobacco, Inc. | Fused heterotetracyclic compounds and use tehreof as hcv polymerase inhibitor |
| US7153848B2 (en) | 2004-08-09 | 2006-12-26 | Bristol-Myers Squibb Company | Inhibitors of HCV replication |
| US7348425B2 (en) | 2004-08-09 | 2008-03-25 | Bristol-Myers Squibb Company | Inhibitors of HCV replication |
| ES2300054T3 (es) | 2004-10-13 | 2008-06-01 | Merck Patent Gmbh | Derivados de la n,n'- difenilurea adecuados como inhibidores de cinasas. |
| AU2005298412B2 (en) | 2004-10-26 | 2011-06-09 | Istituto Di Ricerche Di Biologia Molecolare P Angeletti Spa | Tetracyclic indole derivatives as antiviral agents |
| GB0518390D0 (en) | 2005-09-09 | 2005-10-19 | Angeletti P Ist Richerche Bio | Therapeutic compounds |
| US7399758B2 (en) | 2005-09-12 | 2008-07-15 | Meanwell Nicholas A | Cyclopropyl fused indolobenzazepine HCV NS5B inhibitors |
| US7473688B2 (en) | 2005-09-13 | 2009-01-06 | Bristol-Myers Squibb Company | Indolobenzazepine HCV NS5B inhibitors |
| US7456165B2 (en) | 2006-02-08 | 2008-11-25 | Bristol-Myers Squibb Company | HCV NS5B inhibitors |
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2007
- 2007-02-06 US US11/671,753 patent/US7456165B2/en active Active
- 2007-02-07 EP EP07763294A patent/EP1987038B1/en active Active
- 2007-02-07 AT AT07763294T patent/ATE483712T1/de active
- 2007-02-07 PL PL07763294T patent/PL1987038T3/pl unknown
- 2007-02-07 PT PT07763294T patent/PT1987038E/pt unknown
- 2007-02-07 DE DE602007009646T patent/DE602007009646D1/de active Active
- 2007-02-07 CN CN2007800049834A patent/CN101379066B/zh not_active Expired - Fee Related
- 2007-02-07 SI SI200730453T patent/SI1987038T1/sl unknown
- 2007-02-07 AU AU2007211988A patent/AU2007211988B2/en not_active Ceased
- 2007-02-07 KR KR1020087021812A patent/KR20080102161A/ko not_active Ceased
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- 2007-02-07 WO PCT/US2007/061768 patent/WO2007092888A2/en not_active Ceased
- 2007-02-07 JP JP2008554485A patent/JP5147731B2/ja not_active Expired - Fee Related
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- 2007-02-07 HR HR20100672T patent/HRP20100672T1/hr unknown
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2008
- 2008-08-13 NO NO20083513A patent/NO20083513L/no not_active Application Discontinuation
-
2011
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Also Published As
| Publication number | Publication date |
|---|---|
| PL1987038T3 (pl) | 2011-03-31 |
| SI1987038T1 (sl) | 2011-02-28 |
| ATE483712T1 (de) | 2010-10-15 |
| CN101379066A (zh) | 2009-03-04 |
| JP5147731B2 (ja) | 2013-02-20 |
| CN101379066B (zh) | 2011-08-03 |
| HRP20100672T1 (hr) | 2011-01-31 |
| KR20080102161A (ko) | 2008-11-24 |
| AU2007211988B2 (en) | 2012-02-02 |
| WO2007092888A3 (en) | 2007-10-11 |
| NO20083513L (no) | 2008-10-14 |
| WO2007092888A2 (en) | 2007-08-16 |
| DK1987038T3 (da) | 2011-01-31 |
| US20070185083A1 (en) | 2007-08-09 |
| CY1111423T1 (el) | 2015-08-05 |
| DE602007009646D1 (de) | 2010-11-18 |
| EP1987038A2 (en) | 2008-11-05 |
| AU2007211988A1 (en) | 2007-08-16 |
| EP1987038B1 (en) | 2010-10-06 |
| JP2009526081A (ja) | 2009-07-16 |
| US7456165B2 (en) | 2008-11-25 |
| ES2352574T3 (es) | 2011-02-21 |
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