JP2009506078A5 - - Google Patents
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- JP2009506078A5 JP2009506078A5 JP2008528258A JP2008528258A JP2009506078A5 JP 2009506078 A5 JP2009506078 A5 JP 2009506078A5 JP 2008528258 A JP2008528258 A JP 2008528258A JP 2008528258 A JP2008528258 A JP 2008528258A JP 2009506078 A5 JP2009506078 A5 JP 2009506078A5
- Authority
- JP
- Japan
- Prior art keywords
- optionally substituted
- aliphatic
- compound
- heterocycloaliphatic
- cycloaliphatic
- 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.)
- Granted
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 83
- 125000001931 aliphatic group Chemical group 0.000 claims description 82
- 150000001875 compounds Chemical class 0.000 claims description 82
- 229910052739 hydrogen Inorganic materials 0.000 claims description 51
- 239000001257 hydrogen Substances 0.000 claims description 51
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 42
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 38
- 125000003107 substituted aryl group Chemical group 0.000 claims description 36
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 26
- 239000003112 inhibitor Substances 0.000 claims description 24
- -1 amino, sulfanyl Chemical group 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 125000004429 atom Chemical group 0.000 claims description 19
- 102000012479 Serine Proteases Human genes 0.000 claims description 16
- 108010022999 Serine Proteases Proteins 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 239000003443 antiviral agent Substances 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 8
- 125000003368 amide group Chemical group 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 102000035195 Peptidases Human genes 0.000 claims description 7
- 108091005804 Peptidases Proteins 0.000 claims description 7
- 239000004365 Protease Substances 0.000 claims description 7
- 239000002955 immunomodulating agent Substances 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 208000003311 Cytochrome P-450 Enzyme Inhibitors Diseases 0.000 claims description 6
- 229940122280 Cytochrome P450 inhibitor Drugs 0.000 claims description 6
- 102000006992 Interferon-alpha Human genes 0.000 claims description 6
- 108010047761 Interferon-alpha Proteins 0.000 claims description 6
- 102000003996 Interferon-beta Human genes 0.000 claims description 6
- 108090000467 Interferon-beta Proteins 0.000 claims description 6
- 108010074328 Interferon-gamma Proteins 0.000 claims description 6
- 102000008070 Interferon-gamma Human genes 0.000 claims description 6
- 102000005741 Metalloproteases Human genes 0.000 claims description 6
- 108010006035 Metalloproteases Proteins 0.000 claims description 6
- 108060004795 Methyltransferase Proteins 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
- 108010046075 Thymosin Proteins 0.000 claims description 6
- 102000007501 Thymosin Human genes 0.000 claims description 6
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 claims description 6
- 229960003805 amantadine Drugs 0.000 claims description 6
- 239000002552 dosage form Substances 0.000 claims description 6
- 229940044627 gamma-interferon Drugs 0.000 claims description 6
- 229960000329 ribavirin Drugs 0.000 claims description 6
- 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 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 5
- 230000002519 immonomodulatory effect Effects 0.000 claims description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- 229940124530 sulfonamide Drugs 0.000 claims description 4
- 150000003456 sulfonamides Chemical class 0.000 claims description 4
- NCDNCNXCDXHOMX-UHFFFAOYSA-N Ritonavir Natural products C=1C=CC=CC=1CC(NC(=O)OCC=1SC=NC=1)C(O)CC(CC=1C=CC=CC=1)NC(=O)C(C(C)C)NC(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-UHFFFAOYSA-N 0.000 claims description 3
- 229940122055 Serine protease inhibitor Drugs 0.000 claims description 3
- 101710102218 Serine protease inhibitor Proteins 0.000 claims description 3
- 101800001838 Serine protease/helicase NS3 Proteins 0.000 claims description 3
- 239000002671 adjuvant Substances 0.000 claims description 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
- IQFYYKKMVGJFEH-UHFFFAOYSA-N beta-L-thymidine Natural products O=C1NC(=O)C(C)=CN1C1OC(CO)C(O)C1 IQFYYKKMVGJFEH-UHFFFAOYSA-N 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 208000015181 infectious disease Diseases 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 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 3
- NCDNCNXCDXHOMX-XGKFQTDJSA-N ritonavir Chemical group N([C@@H](C(C)C)C(=O)N[C@H](C[C@H](O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1SC=NC=1)CC=1C=CC=CC=1)C(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-XGKFQTDJSA-N 0.000 claims description 3
- 229960000311 ritonavir Drugs 0.000 claims description 3
- 239000003001 serine protease inhibitor Substances 0.000 claims description 3
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 3
- IQFYYKKMVGJFEH-CSMHCCOUSA-N telbivudine Chemical compound O=C1NC(=O)C(C)=CN1[C@H]1O[C@@H](CO)[C@H](O)C1 IQFYYKKMVGJFEH-CSMHCCOUSA-N 0.000 claims description 3
- 229960005311 telbivudine Drugs 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 2
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 34
- 125000005843 halogen group Chemical group 0.000 claims 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 230000002584 immunomodulator Effects 0.000 claims 5
- 229940121354 immunomodulator Drugs 0.000 claims 5
- 125000002950 monocyclic group Chemical group 0.000 claims 5
- 125000002619 bicyclic group Chemical group 0.000 claims 4
- 239000012472 biological sample Substances 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 238000011109 contamination Methods 0.000 claims 2
- 125000003106 haloaryl group Chemical group 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 1
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims 1
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 1
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 235000019419 proteases Nutrition 0.000 description 3
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 2
- 0 *C1(*)C(*)=NOC1(B1)*N(*)C1C(*)=O Chemical compound *C1(*)C(*)=NOC1(B1)*N(*)C1C(*)=O 0.000 description 2
- 108700010756 Viral Polyproteins Proteins 0.000 description 2
- 239000012620 biological material Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 125000004966 cyanoalkyl group Chemical group 0.000 description 2
- NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 230000003612 virological effect Effects 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- HTFNVAVTYILUCF-UHFFFAOYSA-N 2-[2-ethoxy-4-[4-(4-methylpiperazin-1-yl)piperidine-1-carbonyl]anilino]-5-methyl-11-methylsulfonylpyrimido[4,5-b][1,4]benzodiazepin-6-one Chemical compound CCOc1cc(ccc1Nc1ncc2N(C)C(=O)c3ccccc3N(c2n1)S(C)(=O)=O)C(=O)N1CCC(CC1)N1CCN(C)CC1 HTFNVAVTYILUCF-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 101800000515 Non-structural protein 3 Proteins 0.000 description 1
- 108010076039 Polyproteins Proteins 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 239000003875 Wang resin Substances 0.000 description 1
- 241000710772 Yellow fever virus Species 0.000 description 1
- 101900322197 Yellow fever virus Serine protease NS3 Proteins 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000005214 aminoheteroaryl group Chemical group 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000000601 blood cell Anatomy 0.000 description 1
- 210000001185 bone marrow Anatomy 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 239000000306 component Substances 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 210000002216 heart Anatomy 0.000 description 1
- 108700012707 hepatitis C virus NS3 Proteins 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000004971 nitroalkyl group Chemical group 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 210000000582 semen Anatomy 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000029812 viral genome replication Effects 0.000 description 1
- 229940051021 yellow-fever virus Drugs 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US71153005P | 2005-08-26 | 2005-08-26 | |
| US60/711,530 | 2005-08-26 | ||
| PCT/US2006/033770 WO2007025307A2 (en) | 2005-08-26 | 2006-08-28 | Inhibitors of serine proteases |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009506078A JP2009506078A (ja) | 2009-02-12 |
| JP2009506078A5 true JP2009506078A5 (https=) | 2009-10-15 |
| JP5394063B2 JP5394063B2 (ja) | 2014-01-22 |
Family
ID=37684363
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008528258A Expired - Fee Related JP5394063B2 (ja) | 2005-08-26 | 2006-08-28 | セリンプロテアーゼの阻害剤 |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US7985762B2 (https=) |
| EP (3) | EP2366704B1 (https=) |
| JP (1) | JP5394063B2 (https=) |
| KR (1) | KR20080041715A (https=) |
| CN (1) | CN101316852A (https=) |
| AR (1) | AR055395A1 (https=) |
| AT (1) | ATE530554T1 (https=) |
| AU (1) | AU2006282771B2 (https=) |
| BR (1) | BRPI0615223A2 (https=) |
| CA (1) | CA2620621A1 (https=) |
| EA (1) | EA200800670A1 (https=) |
| EC (1) | ECSP088258A (https=) |
| ES (1) | ES2374943T3 (https=) |
| GE (1) | GEP20115280B (https=) |
| IL (1) | IL189668A0 (https=) |
| MX (1) | MX2008002606A (https=) |
| NO (1) | NO20081467L (https=) |
| NZ (1) | NZ566197A (https=) |
| TW (1) | TW200730533A (https=) |
| WO (1) | WO2007025307A2 (https=) |
| ZA (1) | ZA200801793B (https=) |
Families Citing this family (87)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AP1019A (en) * | 1996-10-18 | 2001-10-16 | Vertex Pharma | Inhibitors of serinre proteases, particularly hepatitis C virus NS3 protease. |
| AU2001251165A1 (en) * | 2000-04-03 | 2001-10-15 | Vertex Pharmaceuticals Incorporated | Inhibitors of serine proteases, particularly hepatitis c virus ns3 protease |
| SV2003000617A (es) | 2000-08-31 | 2003-01-13 | Lilly Co Eli | Inhibidores de la proteasa peptidomimetica ref. x-14912m |
| MY140680A (en) | 2002-05-20 | 2010-01-15 | Bristol Myers Squibb Co | Hepatitis c virus inhibitors |
| WO2004092161A1 (en) * | 2003-04-11 | 2004-10-28 | Vertex Pharmaceuticals Incorporated | Inhibitors of serine proteases, particularly hcv ns3-ns4a protease |
| EP1646642A2 (en) * | 2003-07-18 | 2006-04-19 | Vertex Pharmaceuticals Incorporated | Inhibitors of serine proteases, particularly hcv ns3-ns4a protease |
| UY28500A1 (es) * | 2003-09-05 | 2005-04-29 | Vertex Pharma | Inhibidores de proteasas de serina, en particular proteasa ns3-ns4a del vhc. |
| WO2005028502A1 (en) * | 2003-09-18 | 2005-03-31 | Vertex Pharmaceuticals, Incorporated | Inhibitors of serine proteases, particularly hcv ns3-ns4a protease |
| WO2005037860A2 (en) * | 2003-10-10 | 2005-04-28 | Vertex Pharmaceuticals Incoporated | Inhibitors of serine proteases, particularly hcv ns3-ns4a protease |
| CA2543696A1 (en) * | 2003-10-27 | 2005-05-12 | Vertex Pharmaceuticals Incorporated | Combinations for hcv treatment |
| WO2005077969A2 (en) * | 2004-02-04 | 2005-08-25 | Vertex Pharmaceuticals Incorporated | Inhibitors of serine proteases, particularly hcv ns3-ns4a protease |
| AU2006276246B2 (en) | 2005-07-25 | 2012-09-27 | Intermune, Inc. | Novel macrocyclic inhibitors of hepatitis C virus replication |
| US8399615B2 (en) | 2005-08-19 | 2013-03-19 | Vertex Pharmaceuticals Incorporated | Processes and intermediates |
| US7964624B1 (en) * | 2005-08-26 | 2011-06-21 | Vertex Pharmaceuticals Incorporated | Inhibitors of serine proteases |
| AR055395A1 (es) | 2005-08-26 | 2007-08-22 | Vertex Pharma | Compuestos inhibidores de la actividad de la serina proteasa ns3-ns4a del virus de la hepatitis c |
| AU2007217355B2 (en) | 2006-02-27 | 2012-06-21 | Vertex Pharmaceuticals Incorporated | Co-crystals comprising VX-950 and pharmaceutical compositions comprising the same |
| WO2007109080A2 (en) | 2006-03-16 | 2007-09-27 | Vertex Pharmaceuticals Incorporated | Deuterated hepatitis c protease inhibitors |
| AU2007249668B2 (en) | 2006-04-11 | 2011-04-07 | Novartis Ag | HCV/HIV inhibitors and their uses |
| US7935670B2 (en) | 2006-07-11 | 2011-05-03 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| NZ575186A (en) * | 2006-08-28 | 2012-03-30 | Vertex Pharma | Method for identifying protease inhibitors |
| EA200900472A1 (ru) * | 2006-09-22 | 2009-10-30 | Ранбакси Лабораторис Лимитед | Ингибиторы фосфодиэстеразы iv типа |
| US8343477B2 (en) | 2006-11-01 | 2013-01-01 | Bristol-Myers Squibb Company | Inhibitors of hepatitis C virus |
| US7772180B2 (en) | 2006-11-09 | 2010-08-10 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8003604B2 (en) | 2006-11-16 | 2011-08-23 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US7763584B2 (en) | 2006-11-16 | 2010-07-27 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US7888464B2 (en) | 2006-11-16 | 2011-02-15 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| 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 |
| HRP20120330T1 (hr) | 2007-02-27 | 2012-05-31 | Vertex Pharmaceuticals Incorporated | Sukristali i farmaceutski pripravci koji ih sadrže |
| WO2008106058A2 (en) * | 2007-02-27 | 2008-09-04 | Vertex Pharmaceuticals Incorporated | Inhibitors of serine proteases |
| FR2914920B1 (fr) * | 2007-04-11 | 2011-09-09 | Clariant Specialty Fine Chem F | Procede de deacetalisation d'alpha-aminoacetals. |
| ES2381410T3 (es) | 2007-05-04 | 2012-05-28 | Vertex Pharmceuticals Incorporated | Terapia de combinación paa el tratamiento de infecciones por VHC |
| JP2010526834A (ja) * | 2007-05-10 | 2010-08-05 | インターミューン・インコーポレーテッド | Ｃ型肝炎ウイルス複製の新規ペプチド阻害剤 |
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- 2006-08-28 CA CA002620621A patent/CA2620621A1/en not_active Abandoned
- 2006-08-28 KR KR1020087007149A patent/KR20080041715A/ko not_active Ceased
- 2006-08-28 AU AU2006282771A patent/AU2006282771B2/en not_active Ceased
- 2006-08-28 BR BRPI0615223-6A patent/BRPI0615223A2/pt not_active IP Right Cessation
- 2006-08-28 NZ NZ566197A patent/NZ566197A/en not_active IP Right Cessation
- 2006-08-28 JP JP2008528258A patent/JP5394063B2/ja not_active Expired - Fee Related
- 2006-08-28 CN CNA2006800390595A patent/CN101316852A/zh active Pending
- 2006-08-28 EP EP10182604.8A patent/EP2366704B1/en not_active Not-in-force
- 2006-08-28 WO PCT/US2006/033770 patent/WO2007025307A2/en not_active Ceased
- 2006-08-28 ES ES06813916T patent/ES2374943T3/es active Active
- 2006-08-28 TW TW095131649A patent/TW200730533A/zh unknown
- 2006-08-28 MX MX2008002606A patent/MX2008002606A/es active IP Right Grant
- 2006-08-28 US US11/511,109 patent/US7985762B2/en not_active Expired - Fee Related
- 2006-08-28 EP EP06813916A patent/EP1917269B1/en active Active
- 2006-08-28 EA EA200800670A patent/EA200800670A1/ru unknown
- 2006-08-28 GE GEAP200610581A patent/GEP20115280B/en unknown
- 2006-08-28 EP EP10176969A patent/EP2364984A1/en not_active Withdrawn
- 2006-08-28 AT AT06813916T patent/ATE530554T1/de not_active IP Right Cessation
-
2008
- 2008-02-21 IL IL189668A patent/IL189668A0/en unknown
- 2008-02-25 ZA ZA200801793A patent/ZA200801793B/xx unknown
- 2008-03-10 EC EC2008008258A patent/ECSP088258A/es unknown
- 2008-03-25 NO NO20081467A patent/NO20081467L/no not_active Application Discontinuation
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2011
- 2011-02-28 US US13/036,930 patent/US8440706B2/en not_active Expired - Fee Related
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