NZ549697A - Macrocyclic compounds as inhibitors of viral replication - Google Patents
Macrocyclic compounds as inhibitors of viral replicationInfo
- Publication number
- NZ549697A NZ549697A NZ549697A NZ54969705A NZ549697A NZ 549697 A NZ549697 A NZ 549697A NZ 549697 A NZ549697 A NZ 549697A NZ 54969705 A NZ54969705 A NZ 54969705A NZ 549697 A NZ549697 A NZ 549697A
- Authority
- NZ
- New Zealand
- Prior art keywords
- alkyl
- optionally substituted
- hydroxy
- cycloalkyl
- fluoro
- Prior art date
Links
- 239000003112 inhibitor Substances 0.000 title description 3
- 150000002678 macrocyclic compounds Chemical class 0.000 title description 2
- 230000029812 viral genome replication Effects 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 220
- JHRWWRDRBPCWTF-OLQVQODUSA-N captafol Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)C(Cl)Cl)C(=O)[C@H]21 JHRWWRDRBPCWTF-OLQVQODUSA-N 0.000 claims abstract description 22
- 208000010710 hepatitis C virus infection Diseases 0.000 claims abstract description 10
- 208000019425 cirrhosis of liver Diseases 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 1195
- 125000003545 alkoxy group Chemical group 0.000 claims description 579
- 125000001153 fluoro group Chemical group F* 0.000 claims description 554
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 468
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 433
- -1 nitro, hydroxy Chemical group 0.000 claims description 427
- 125000005843 halogen group Chemical group 0.000 claims description 423
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 370
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 300
- 125000003118 aryl group Chemical group 0.000 claims description 166
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 128
- 239000003814 drug Substances 0.000 claims description 117
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 115
- 229910052739 hydrogen Inorganic materials 0.000 claims description 103
- 125000003342 alkenyl group Chemical group 0.000 claims description 89
- 229910052799 carbon Inorganic materials 0.000 claims description 87
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 74
- 229910052760 oxygen Inorganic materials 0.000 claims description 67
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 60
- 229910052717 sulfur Chemical group 0.000 claims description 59
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 52
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 52
- 229910052757 nitrogen Inorganic materials 0.000 claims description 52
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 50
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 49
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 48
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 48
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 48
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 48
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 48
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 46
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 46
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 45
- 125000002971 oxazolyl group Chemical group 0.000 claims description 45
- 125000000335 thiazolyl group Chemical group 0.000 claims description 45
- 125000002541 furyl group Chemical group 0.000 claims description 44
- 125000001544 thienyl group Chemical group 0.000 claims description 44
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 37
- 125000003368 amide group Chemical group 0.000 claims description 36
- 239000001257 hydrogen Substances 0.000 claims description 36
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 36
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 35
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 34
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 34
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 33
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 33
- 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 32
- 229910052721 tungsten Inorganic materials 0.000 claims description 32
- 125000004429 atom Chemical group 0.000 claims description 31
- 125000001072 heteroaryl group Chemical group 0.000 claims description 31
- 125000002757 morpholinyl group Chemical group 0.000 claims description 31
- 125000004193 piperazinyl group Chemical group 0.000 claims description 31
- 125000003386 piperidinyl group Chemical group 0.000 claims description 31
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 31
- 125000000623 heterocyclic group Chemical group 0.000 claims description 30
- 125000004076 pyridyl group Chemical group 0.000 claims description 30
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 30
- 101800001838 Serine protease/helicase NS3 Proteins 0.000 claims description 29
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 29
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 29
- 239000008194 pharmaceutical composition Substances 0.000 claims description 27
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 25
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 25
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 25
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 25
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 25
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 25
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 25
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 24
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 24
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 24
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 24
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 24
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 24
- 229930192474 thiophene Natural products 0.000 claims description 24
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 22
- 125000005842 heteroatom Chemical group 0.000 claims description 20
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 19
- 125000001624 naphthyl group Chemical group 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 19
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 17
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 17
- 239000012453 solvate Substances 0.000 claims description 17
- 239000011593 sulfur Chemical group 0.000 claims description 17
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 12
- 229910052720 vanadium Inorganic materials 0.000 claims description 12
- 101800001554 RNA-directed RNA polymerase Proteins 0.000 claims description 11
- 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 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 230000003993 interaction Effects 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- 239000001301 oxygen Chemical group 0.000 claims description 11
- 229960000329 ribavirin Drugs 0.000 claims description 11
- 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 11
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 238000009472 formulation Methods 0.000 claims description 10
- 125000002883 imidazolyl group Chemical group 0.000 claims description 9
- 125000005647 linker group Chemical group 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 8
- 229920001223 polyethylene glycol Polymers 0.000 claims description 8
- 230000004044 response Effects 0.000 claims description 8
- 230000003612 virological effect Effects 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 230000001965 increasing effect Effects 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 7
- 229930194542 Keto Natural products 0.000 claims description 6
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 claims description 6
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 6
- 125000000033 alkoxyamino group Chemical group 0.000 claims description 6
- 125000005157 alkyl carboxy group Chemical group 0.000 claims description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 6
- 125000000468 ketone group Chemical group 0.000 claims description 6
- 210000004185 liver Anatomy 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 150000005846 sugar alcohols Chemical class 0.000 claims description 6
- 125000001174 sulfone group Chemical group 0.000 claims description 6
- 230000002459 sustained effect Effects 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- VGUNCVGRXFWLAS-UHFFFAOYSA-N thiophen-2-yl N-[carbamoyl(phenoxy)amino]sulfamate Chemical compound O(C1=CC=CC=C1)N(C(=O)N)NS(=O)(=O)OC=1SC=CC1 VGUNCVGRXFWLAS-UHFFFAOYSA-N 0.000 claims description 5
- 108091005804 Peptidases Proteins 0.000 claims description 4
- 239000004365 Protease Substances 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 230000003908 liver function Effects 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 108010047761 Interferon-alpha Proteins 0.000 claims 90
- 102000006992 Interferon-alpha Human genes 0.000 claims 90
- 239000002777 nucleoside Substances 0.000 claims 27
- 150000003833 nucleoside derivatives Chemical class 0.000 claims 18
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical group C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 14
- UJQBOUAGWGVOTI-XSSZXYGBSA-N 1-[(2r,4s,5r)-4-azido-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@](O)(N=[N+]=[N-])C1 UJQBOUAGWGVOTI-XSSZXYGBSA-N 0.000 claims 9
- IWUCXVSUMQZMFG-RGDLXGNYSA-N 1-[(2s,3s,4r,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxamide Chemical compound N1=C(C(=O)N)N=CN1[C@@H]1[C@@H](O)[C@@H](O)[C@H](CO)O1 IWUCXVSUMQZMFG-RGDLXGNYSA-N 0.000 claims 9
- TZYVRXZQAWPIAB-FCLHUMLKSA-N 5-amino-3-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4h-[1,3]thiazolo[4,5-d]pyrimidine-2,7-dione Chemical compound O=C1SC=2C(=O)NC(N)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O TZYVRXZQAWPIAB-FCLHUMLKSA-N 0.000 claims 9
- VWFCHDSQECPREK-LURJTMIESA-N Cidofovir Chemical compound NC=1C=CN(C[C@@H](CO)OCP(O)(O)=O)C(=O)N=1 VWFCHDSQECPREK-LURJTMIESA-N 0.000 claims 9
- BXZVVICBKDXVGW-NKWVEPMBSA-N Didanosine Chemical compound O1[C@H](CO)CC[C@@H]1N1C(NC=NC2=O)=C2N=C1 BXZVVICBKDXVGW-NKWVEPMBSA-N 0.000 claims 9
- 229940121740 Inosine monophosphate dehydrogenase inhibitor Drugs 0.000 claims 9
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- GLWHPRRGGYLLRV-XLPZGREQSA-N [[(2s,3s,5r)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](N=[N+]=[N-])C1 GLWHPRRGGYLLRV-XLPZGREQSA-N 0.000 claims 9
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- MCGSCOLBFJQGHM-SCZZXKLOSA-N abacavir Chemical compound C=12N=CN([C@H]3C=C[C@@H](CO)C3)C2=NC(N)=NC=1NC1CC1 MCGSCOLBFJQGHM-SCZZXKLOSA-N 0.000 claims 9
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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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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Virology (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Gastroenterology & Hepatology (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Proteomics, Peptides & Aminoacids (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 (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US55816104P | 2004-03-30 | 2004-03-30 | |
| US56241804P | 2004-04-14 | 2004-04-14 | |
| US61238104P | 2004-09-22 | 2004-09-22 | |
| US61246004P | 2004-09-22 | 2004-09-22 | |
| PCT/US2005/010494 WO2005095403A2 (en) | 2004-03-30 | 2005-03-29 | Macrocyclic compounds as inhibitors of viral replication |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ549697A true NZ549697A (en) | 2009-12-24 |
Family
ID=35005653
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ549697A NZ549697A (en) | 2004-03-30 | 2005-03-29 | Macrocyclic compounds as inhibitors of viral replication |
Country Status (16)
| Country | Link |
|---|---|
| EP (1) | EP1749007A2 (https=) |
| JP (1) | JP4950026B2 (https=) |
| AP (1) | AP2006003763A0 (https=) |
| AR (1) | AR050321A1 (https=) |
| AU (1) | AU2005228894B9 (https=) |
| BR (1) | BRPI0509467A (https=) |
| CA (1) | CA2560897C (https=) |
| CU (1) | CU23787B7 (https=) |
| EA (1) | EA012389B1 (https=) |
| EC (1) | ECSP066959A (https=) |
| GE (1) | GEP20104926B (https=) |
| IL (1) | IL177917A0 (https=) |
| MA (1) | MA28548B1 (https=) |
| NO (1) | NO20064933L (https=) |
| NZ (1) | NZ549697A (https=) |
| WO (1) | WO2005095403A2 (https=) |
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| MY140680A (en) | 2002-05-20 | 2010-01-15 | Bristol Myers Squibb Co | Hepatitis c virus inhibitors |
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| UA91341C2 (ru) | 2004-07-15 | 2010-07-26 | Амр Текнолоджи, Інк. | Арил- и гетероарилзамещенные тетрагидроизохинолины и их применение для блокирования обратного захвата норэпинефрина, допамина и серотонина |
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| AU2006276246B2 (en) | 2005-07-25 | 2012-09-27 | Intermune, Inc. | Novel macrocyclic inhibitors of hepatitis C virus replication |
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| US7763584B2 (en) * | 2006-11-16 | 2010-07-27 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
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| PL2468724T3 (pl) | 2006-12-21 | 2016-05-31 | Zealand Pharma As | Synteza związków pirolidynowych |
| WO2008086161A1 (en) * | 2007-01-08 | 2008-07-17 | Phenomix Corporation | Macrocyclic hepatitis c protease inhibitors |
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| JP2010519339A (ja) | 2007-02-26 | 2010-06-03 | アキリオン ファーマシューティカルズ，インコーポレーテッド | Ｈｃｖ複製阻害剤として有用な三級アミン置換ペプチド |
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| US10201584B1 (en) | 2011-05-17 | 2019-02-12 | Abbvie Inc. | Compositions and methods for treating HCV |
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| US8889159B2 (en) | 2011-11-29 | 2014-11-18 | Gilead Pharmasset Llc | Compositions and methods for treating hepatitis C virus |
| JP6215315B2 (ja) | 2012-06-12 | 2017-10-18 | アッヴィ・インコーポレイテッド | ピリジノンおよびピリダジノン誘導体 |
| EA025560B1 (ru) | 2012-10-19 | 2017-01-30 | Бристол-Майерс Сквибб Компани | Ингибиторы вируса гепатита с |
| US9643999B2 (en) | 2012-11-02 | 2017-05-09 | 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 |
| EA201690473A1 (ru) | 2013-08-27 | 2017-03-31 | ГАЙЛИД ФАРМАССЕТ ЭлЭлСи | Комбинированный состав двух противовирусных соединений |
| EP3089757A1 (en) | 2014-01-03 | 2016-11-09 | AbbVie Inc. | Solid antiviral dosage forms |
| JP6989864B2 (ja) | 2017-05-05 | 2022-02-03 | ジーランド ファーマ，アー／エス | ギャップ結合細胞間コミュニケーションモジュレータ及び糖尿病性眼疾患の治療のためのそれらの使用 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6323180B1 (en) * | 1998-08-10 | 2001-11-27 | Boehringer Ingelheim (Canada) Ltd | Hepatitis C inhibitor tri-peptides |
| AR022061A1 (es) * | 1998-08-10 | 2002-09-04 | Boehringer Ingelheim Ca Ltd | Peptidos inhibidores de la hepatitis c, una composicion farmaceutica que los contiene, el uso de los mismos para preparar una composicion farmaceutica, el uso de un producto intermedio para la preparacion de estos peptidos y un procedimiento para la preparacion de un peptido analogo de los mismos. |
| 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 |
| US6608027B1 (en) * | 1999-04-06 | 2003-08-19 | Boehringer Ingelheim (Canada) Ltd | Macrocyclic peptides active against the hepatitis C virus |
| ES2263687T3 (es) * | 2000-11-20 | 2006-12-16 | Bristol-Myers Squibb Company | Inhibidores tripeptidicos de la hepatitis c. |
| US6867185B2 (en) * | 2001-12-20 | 2005-03-15 | Bristol-Myers Squibb Company | Inhibitors of hepatitis C virus |
| CA2369711A1 (en) * | 2002-01-30 | 2003-07-30 | Boehringer Ingelheim (Canada) Ltd. | Macrocyclic peptides active against the hepatitis c virus |
| CA2370396A1 (en) * | 2002-02-01 | 2003-08-01 | Boehringer Ingelheim (Canada) Ltd. | Hepatitis c inhibitor tri-peptides |
| CA2369970A1 (en) * | 2002-02-01 | 2003-08-01 | Boehringer Ingelheim (Canada) Ltd. | Hepatitis c inhibitor tri-peptides |
| US6828301B2 (en) * | 2002-02-07 | 2004-12-07 | Boehringer Ingelheim International Gmbh | Pharmaceutical compositions for hepatitis C viral protease inhibitors |
| ATE481106T1 (de) * | 2002-05-20 | 2010-10-15 | Bristol Myers Squibb Co | Heterocyclische sulfonamid-hepatitis-c-virus- hemmer |
| MY140680A (en) * | 2002-05-20 | 2010-01-15 | Bristol Myers Squibb Co | Hepatitis c virus inhibitors |
| HRP20130098T1 (hr) * | 2003-10-14 | 2013-02-28 | F. Hoffmann - La Roche Ag | MAKROCIKLIÄŚKE KARBOKSILNE KISELINE I ACILSULFONAMIDNI SPOJEVI KAO INHIBITORI REPLIKACIJE HCV-a |
| PL1713822T3 (pl) * | 2004-01-30 | 2010-08-31 | Medivir Ab | Inhibitory proteazy serynowej HCV NS-3 |
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2005
- 2005-03-29 BR BRPI0509467-4A patent/BRPI0509467A/pt not_active IP Right Cessation
- 2005-03-29 NZ NZ549697A patent/NZ549697A/en not_active IP Right Cessation
- 2005-03-29 GE GEAP20059674A patent/GEP20104926B/en unknown
- 2005-03-29 CA CA2560897A patent/CA2560897C/en not_active Expired - Fee Related
- 2005-03-29 AP AP2006003763A patent/AP2006003763A0/xx unknown
- 2005-03-29 EP EP05757750A patent/EP1749007A2/en not_active Withdrawn
- 2005-03-29 EA EA200601467A patent/EA012389B1/ru not_active IP Right Cessation
- 2005-03-29 JP JP2007506466A patent/JP4950026B2/ja not_active Expired - Fee Related
- 2005-03-29 WO PCT/US2005/010494 patent/WO2005095403A2/en not_active Ceased
- 2005-03-29 AU AU2005228894A patent/AU2005228894B9/en not_active Ceased
- 2005-03-30 AR ARP050101257A patent/AR050321A1/es not_active Application Discontinuation
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2006
- 2006-09-06 IL IL177917A patent/IL177917A0/en unknown
- 2006-10-20 MA MA29407A patent/MA28548B1/fr unknown
- 2006-10-27 EC EC2006006959A patent/ECSP066959A/es unknown
- 2006-10-27 NO NO20064933A patent/NO20064933L/no not_active Application Discontinuation
-
2009
- 2009-12-08 CU CU20090209A patent/CU23787B7/es active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| NO20064933L (no) | 2006-12-15 |
| BRPI0509467A (pt) | 2007-09-11 |
| AU2005228894A1 (en) | 2005-10-13 |
| AP2006003763A0 (en) | 2006-10-31 |
| MA28548B1 (fr) | 2007-04-03 |
| IL177917A0 (en) | 2006-12-31 |
| EP1749007A2 (en) | 2007-02-07 |
| AR050321A1 (es) | 2006-10-18 |
| ECSP066959A (es) | 2006-12-20 |
| JP4950026B2 (ja) | 2012-06-13 |
| AU2005228894B9 (en) | 2011-10-13 |
| EA012389B1 (ru) | 2009-10-30 |
| CU20090209A7 (es) | 2011-04-26 |
| JP2007531749A (ja) | 2007-11-08 |
| WO2005095403A3 (en) | 2005-12-01 |
| EA200601467A1 (ru) | 2007-06-29 |
| AU2005228894B2 (en) | 2011-08-25 |
| CA2560897C (en) | 2012-06-12 |
| CA2560897A1 (en) | 2005-10-13 |
| CU23787B7 (es) | 2012-03-15 |
| WO2005095403A2 (en) | 2005-10-13 |
| GEP20104926B (en) | 2010-03-25 |
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