JP2003531199A5 - - Google Patents
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- JP2003531199A5 JP2003531199A5 JP2001578418A JP2001578418A JP2003531199A5 JP 2003531199 A5 JP2003531199 A5 JP 2003531199A5 JP 2001578418 A JP2001578418 A JP 2001578418A JP 2001578418 A JP2001578418 A JP 2001578418A JP 2003531199 A5 JP2003531199 A5 JP 2003531199A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- aryl
- conhch
- compound
- heteroaryl
- 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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- 0 CCC*(C(C(NCC(NC(C(O)=O)C1=CC=CCC1)=C)=O)O)NC(C(*c1cc(CCCCCCCC(N[C@]2C3CCCCC3)=O)ccc1)NC2=O)=O Chemical compound CCC*(C(C(NCC(NC(C(O)=O)C1=CC=CCC1)=C)=O)O)NC(C(*c1cc(CCCCCCCC(N[C@]2C3CCCCC3)=O)ccc1)NC2=O)=O 0.000 description 38
- 125000000217 alkyl group Chemical group 0.000 description 27
- 150000001875 compounds Chemical class 0.000 description 26
- -1 aryl-heteroaryl Chemical group 0.000 description 19
- 125000000753 cycloalkyl group Chemical group 0.000 description 13
- 125000003118 aryl group Chemical group 0.000 description 12
- 229910052760 oxygen Inorganic materials 0.000 description 10
- 125000002877 alkyl aryl group Chemical group 0.000 description 8
- 125000001072 heteroaryl group Chemical group 0.000 description 8
- 101800001838 Serine protease/helicase NS3 Proteins 0.000 description 7
- 125000004404 heteroalkyl group Chemical group 0.000 description 7
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 6
- 125000005213 alkyl heteroaryl group Chemical group 0.000 description 5
- 235000013877 carbamide Nutrition 0.000 description 5
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 108091005804 Peptidases Proteins 0.000 description 4
- 239000004365 Protease Substances 0.000 description 4
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000004414 alkyl thio group Chemical group 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 3
- 208000005176 Hepatitis C Diseases 0.000 description 3
- 101710144111 Non-structural protein 3 Proteins 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 125000005110 aryl thio group Chemical group 0.000 description 3
- 125000004104 aryloxy group Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000003937 drug carrier Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 2
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 102000014150 Interferons Human genes 0.000 description 2
- 108010050904 Interferons Proteins 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 2
- 150000005215 alkyl ethers Chemical class 0.000 description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
- 125000004422 alkyl sulphonamide group Chemical group 0.000 description 2
- 239000003443 antiviral agent Substances 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000000113 cyclohexyl group Chemical class [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical class [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 229940079322 interferon Drugs 0.000 description 2
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 125000004437 phosphorous atom Chemical group 0.000 description 2
- 125000004076 pyridyl group Chemical class 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 125000001544 thienyl group Chemical class 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- 125000004008 6 membered carbocyclic group Chemical group 0.000 description 1
- MTYIELILHRTMRW-QVOQEABFSA-N CC(C(C(NCC(NC(C(O)=O)c1ccccc1)=O)=O)=O)NC(C(CC(CC=C1)C=C1OCCCCCC(C(N[C@H]1C2CCCCC2)=O)=C)NC1=O)=O Chemical compound CC(C(C(NCC(NC(C(O)=O)c1ccccc1)=O)=O)=O)NC(C(CC(CC=C1)C=C1OCCCCCC(C(N[C@H]1C2CCCCC2)=O)=C)NC1=O)=O MTYIELILHRTMRW-QVOQEABFSA-N 0.000 description 1
- BYKYPYPHULOVEW-UHFFFAOYSA-N CC(C)C(CC1)CCC1(F)F Chemical compound CC(C)C(CC1)CCC1(F)F BYKYPYPHULOVEW-UHFFFAOYSA-N 0.000 description 1
- DWPMJTVAEDBIES-UHFFFAOYSA-N CC(CC1)CCN1C(C)=O Chemical compound CC(CC1)CCN1C(C)=O DWPMJTVAEDBIES-UHFFFAOYSA-N 0.000 description 1
- BPNDWFMXDNUGNH-SQIAPHFMSA-N CCCC(C(C(NCC(NC(C(N)=C1CC1)c1ccccc1)O)O)=O)NC(C(CCCCNC(Cc1ccc(CC(N[C@H]2C3CCCCC3)=C)cc1)=O)NC2=O)=O Chemical compound CCCC(C(C(NCC(NC(C(N)=C1CC1)c1ccccc1)O)O)=O)NC(C(CCCCNC(Cc1ccc(CC(N[C@H]2C3CCCCC3)=C)cc1)=O)NC2=O)=O BPNDWFMXDNUGNH-SQIAPHFMSA-N 0.000 description 1
- IBTHWBCNCFKRJY-MHARVHOESA-N CCCC(C(C(NCC(NC(C(N)O)C1=CC=CCC1)=O)O)=O)NC(C(CCCCNC(Cc1ccc(CC(N[C@H]2C3CCCCC3)=O)cc1)=O)NC2=O)=O Chemical compound CCCC(C(C(NCC(NC(C(N)O)C1=CC=CCC1)=O)O)=O)NC(C(CCCCNC(Cc1ccc(CC(N[C@H]2C3CCCCC3)=O)cc1)=O)NC2=O)=O IBTHWBCNCFKRJY-MHARVHOESA-N 0.000 description 1
- XQAJKBOJKGQFQW-RKJAHWQASA-N CCCC(C(C(NCC(NC(C(O)=O)C1=CCCC=C1)=O)=O)=O)NC(C(Cc1cccc(Oc2ccc(CCCCC(CCC[C@H]3C)=O)cc2)c1)NC3=O)=O Chemical compound CCCC(C(C(NCC(NC(C(O)=O)C1=CCCC=C1)=O)=O)=O)NC(C(Cc1cccc(Oc2ccc(CCCCC(CCC[C@H]3C)=O)cc2)c1)NC3=O)=O XQAJKBOJKGQFQW-RKJAHWQASA-N 0.000 description 1
- 101100391182 Dictyostelium discoideum forI gene Proteins 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 102000006992 Interferon-alpha Human genes 0.000 description 1
- 108010047761 Interferon-alpha Proteins 0.000 description 1
- 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 description 1
- 229940100389 Sulfonylurea Drugs 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000004947 alkyl aryl amino group Chemical group 0.000 description 1
- 150000004789 alkyl aryl sulfoxides Chemical class 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000005100 aryl amino carbonyl group Chemical group 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 125000005129 aryl carbonyl group Chemical group 0.000 description 1
- 150000008378 aryl ethers Chemical class 0.000 description 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 1
- 125000005362 aryl sulfone group Chemical group 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- UZMZVDOOVXLRID-UHFFFAOYSA-N azanylidyne-(nitrosulfonylamino)methane Chemical class [O-][N+](=O)S(=O)(=O)NC#N UZMZVDOOVXLRID-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- NMGFRGWSRHOQOP-UHFFFAOYSA-N carbamic acid;urea Chemical compound NC(N)=O.NC(O)=O NMGFRGWSRHOQOP-UHFFFAOYSA-N 0.000 description 1
- OWIUPIRUAQMTTK-UHFFFAOYSA-N carbazic acid Chemical compound NNC(O)=O OWIUPIRUAQMTTK-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001559 cyclopropyl group Chemical class [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000004475 heteroaralkyl group Chemical group 0.000 description 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 1
- 125000005222 heteroarylaminocarbonyl group Chemical group 0.000 description 1
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 description 1
- 125000005226 heteroaryloxycarbonyl group Chemical group 0.000 description 1
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 150000002678 macrocyclic compounds Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- MGQNMYSRDBFUIR-UHFFFAOYSA-N nitro cyanoformate Chemical compound [O-][N+](=O)OC(=O)C#N MGQNMYSRDBFUIR-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 125000005936 piperidyl group Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 229960000329 ribavirin Drugs 0.000 description 1
- 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 1
- 239000012453 solvate Substances 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US19820400P | 2000-04-19 | 2000-04-19 | |
| US60/198,204 | 2000-04-19 | ||
| PCT/US2001/012530 WO2001081325A2 (en) | 2000-04-19 | 2001-04-17 | Macrocyclic ns3-serine protease inhibitors of hepatitis c virus comprising alkyl and aryl alanine p2 moieties |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003531199A JP2003531199A (ja) | 2003-10-21 |
| JP2003531199A5 true JP2003531199A5 (https=) | 2008-02-28 |
| JP4748912B2 JP4748912B2 (ja) | 2011-08-17 |
Family
ID=22732422
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001578418A Expired - Fee Related JP4748912B2 (ja) | 2000-04-19 | 2001-04-17 | アルキルおよびアリールアラニンｐ２部分を含むｃ型肝炎ウイルスに対する大員環ｎｓ３−セリンプロテアーゼ阻害剤 |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US6914122B2 (https=) |
| EP (1) | EP1274724A2 (https=) |
| JP (1) | JP4748912B2 (https=) |
| KR (1) | KR20020097220A (https=) |
| CN (3) | CN101580536A (https=) |
| AR (1) | AR030558A1 (https=) |
| AU (1) | AU2001253621A1 (https=) |
| BR (1) | BR0110104A (https=) |
| CA (1) | CA2406532A1 (https=) |
| CZ (1) | CZ20023473A3 (https=) |
| HK (1) | HK1048479A1 (https=) |
| HU (1) | HUP0302957A2 (https=) |
| IL (1) | IL151935A0 (https=) |
| MX (1) | MXPA02010375A (https=) |
| NO (1) | NO20025030L (https=) |
| NZ (1) | NZ521456A (https=) |
| PE (1) | PE20011288A1 (https=) |
| PL (1) | PL358591A1 (https=) |
| RU (1) | RU2002131163A (https=) |
| SK (1) | SK14952002A3 (https=) |
| WO (1) | WO2001081325A2 (https=) |
| ZA (1) | ZA200208014B (https=) |
Families Citing this family (136)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100509388B1 (ko) * | 1996-10-18 | 2005-08-23 | 버텍스 파마슈티칼스 인코포레이티드 | 세린 프로테아제, 특히 간염 ｃ 바이러스 ｎｓ３ 프로테아제의 저해제 |
| US6608027B1 (en) | 1999-04-06 | 2003-08-19 | Boehringer Ingelheim (Canada) Ltd | Macrocyclic peptides active against the hepatitis C virus |
| SV2003000617A (es) | 2000-08-31 | 2003-01-13 | Lilly Co Eli | Inhibidores de la proteasa peptidomimetica ref. x-14912m |
| KR20030091946A (ko) * | 2000-12-12 | 2003-12-03 | 쉐링 코포레이션 | Ｃ형 간염 바이러스의 ｎｓ3-세린 프로테아제억제제로서의 디아릴 펩티드 |
| SK286630B6 (sk) | 2001-01-22 | 2009-02-05 | Merck & Co., Inc. | Nukleozidové deriváty, farmaceutický prostriedok s ich obsahom a ich použitie |
| US7119072B2 (en) | 2002-01-30 | 2006-10-10 | Boehringer Ingelheim (Canada) Ltd. | Macrocyclic peptides active against the hepatitis C virus |
| US6642204B2 (en) | 2002-02-01 | 2003-11-04 | Boehringer Ingelheim International Gmbh | Hepatitis C inhibitor tri-peptides |
| US7091184B2 (en) | 2002-02-01 | 2006-08-15 | Boehringer Ingelheim International Gmbh | Hepatitis C inhibitor tri-peptides |
| KR20040099425A (ko) * | 2002-04-11 | 2004-11-26 | 버텍스 파마슈티칼스 인코포레이티드 | 세린 프로테아제, 특히 ｃ형 간염 바이러스 ｎｓ3-ｎｓ4프로테아제의 억제제 |
| US20050075279A1 (en) | 2002-10-25 | 2005-04-07 | Boehringer Ingelheim International Gmbh | Macrocyclic peptides active against the hepatitis C virus |
| CL2004001161A1 (es) | 2003-05-21 | 2005-04-08 | Boehringer Ingelheim Int | Compuestos describe compuestos derivados de quinolina; composicion farmaceutica; y su uso para tratar una enfermedad causada por el virus de la hepatitis c. |
| US20090198050A1 (en) * | 2003-06-18 | 2009-08-06 | Tranzyme Pharma Inc. | Macrocyclic Modulators of the Ghrelin Receptor |
| US7476653B2 (en) * | 2003-06-18 | 2009-01-13 | Tranzyme Pharma, Inc. | Macrocyclic modulators of the ghrelin receptor |
| US8921521B2 (en) | 2003-06-18 | 2014-12-30 | Ocera Therapeutics, Inc. | Macrocyclic modulators of the Ghrelin receptor |
| DK1633774T3 (da) | 2003-06-18 | 2010-05-25 | Tranzyme Pharma Inc | Makrocykliske motilinreceptorantagonister |
| US7449447B2 (en) | 2003-08-26 | 2008-11-11 | Schering Corporation | Peptidomimetic NS3-serine protease inhibitors of hepatitis C virus |
| TWI359147B (en) | 2003-09-05 | 2012-03-01 | Vertex Pharma | Inhibitors of serine proteases, particularly hcv n |
| ES2361997T3 (es) | 2003-09-22 | 2011-06-27 | Boehringer Ingelheim International Gmbh | Péptidos macrocíclicos activos contra el virus de la hepatitis c. |
| RU2006113880A (ru) * | 2003-09-26 | 2007-11-20 | Шеринг Корпорейшн (US) | Макроциклические ингибиторы сериновой протеиназы ns3 вируса гепатита с |
| WO2005037860A2 (en) | 2003-10-10 | 2005-04-28 | Vertex Pharmaceuticals Incoporated | Inhibitors of serine proteases, particularly hcv ns3-ns4a protease |
| US7491794B2 (en) * | 2003-10-14 | 2009-02-17 | Intermune, Inc. | Macrocyclic compounds as inhibitors of viral replication |
| US8187874B2 (en) | 2003-10-27 | 2012-05-29 | Vertex Pharmaceuticals Incorporated | Drug discovery method |
| EP1944042A1 (en) | 2003-10-27 | 2008-07-16 | Vertex Pharmceuticals Incorporated | Combinations for HCV treatment |
| MXPA06005683A (es) | 2003-11-20 | 2006-12-14 | Schering Corp | Inhibidores despeptidizados de la proteasa ns3 del virus de la hepatitis c. |
| ATE495185T1 (de) | 2004-01-21 | 2011-01-15 | Boehringer Ingelheim Int | Makrocyclische peptide mit wirkung gegen das hepatitis-c-virus |
| CN1938332B (zh) | 2004-02-04 | 2011-10-19 | 沃泰克斯药物股份有限公司 | 丝氨酸蛋白酶、特别是hcv ns3-ns4a蛋白酶的抑制剂 |
| US7816326B2 (en) | 2004-02-27 | 2010-10-19 | Schering Corporation | Sulfur compounds as inhibitors of hepatitis C virus NS3 serine protease |
| CN1946691A (zh) | 2004-02-27 | 2007-04-11 | 先灵公司 | 作为丙型肝炎病毒ns3丝氨酸蛋白酶抑制剂的化合物 |
| AU2005219859A1 (en) | 2004-02-27 | 2005-09-15 | Schering Corporation | Inhibitors of hepatitis C virus NS3 protease |
| DE602005021760D1 (de) | 2004-02-27 | 2010-07-22 | Schering Corp | Schwefelverbindungen als inhibitoren der ns3-serinprotease des hepatitis-c-virus |
| US7186747B2 (en) | 2004-02-27 | 2007-03-06 | Schering Corporation | Compounds as inhibitors of hepatitis C virus NS3 serine protease |
| EP1737821B1 (en) | 2004-02-27 | 2009-08-05 | Schering Corporation | 3,4-(cyclopentyl)-fused proline compounds as inhibitors of hepatitis c virus ns3 serine protease |
| ES2328596T3 (es) | 2004-05-20 | 2009-11-16 | Schering Corporation | Prolinas sustituidas como inhibidores de la serina proteasa del virus ns3 de la hepatitis c. |
| JP4914355B2 (ja) | 2004-07-20 | 2012-04-11 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｃ型肝炎インヒビターペプチド類似体 |
| UY29016A1 (es) | 2004-07-20 | 2006-02-24 | Boehringer Ingelheim Int | Analogos de dipeptidos inhibidores de la hepatitis c |
| ATE513844T1 (de) | 2004-08-27 | 2011-07-15 | Schering Corp | Acylsulfonamidverbindungen als inhibitoren der ns3-serinprotease des hepatitis-c-virus |
| WO2007001406A2 (en) * | 2004-10-05 | 2007-01-04 | Chiron Corporation | Aryl-containing macrocyclic compounds |
| NZ563365A (en) * | 2005-06-02 | 2011-02-25 | Schering Corp | Combination of HCV protease inhibitors with a surfactant |
| AU2006252519B2 (en) | 2005-06-02 | 2012-08-30 | Merck Sharp & Dohme Corp. | HCV protease inhibitors in combination with food |
| US20070237818A1 (en) * | 2005-06-02 | 2007-10-11 | Malcolm Bruce A | Controlled-release formulation of HCV protease inhibitor and methods using the same |
| US20110104109A1 (en) * | 2005-07-13 | 2011-05-05 | Frank Bennett | Tetracyclic indole derivatives and their use for treating or preventing viral infections |
| MX2008001166A (es) | 2005-07-25 | 2008-03-18 | Intermune Inc | Nuevos inhibidores macrociclicos de la replicacion del virus de hepatitis c. |
| JP5230416B2 (ja) * | 2005-07-29 | 2013-07-10 | テイボテク・フアーマシユーチカルズ | Ｃ型肝炎ウイルスの大員環状阻害剤 |
| KR20080033481A (ko) * | 2005-08-02 | 2008-04-16 | 버텍스 파마슈티칼스 인코포레이티드 | 세린 프로테아제의 억제제 |
| PL385229A1 (pl) | 2005-08-19 | 2008-09-29 | Vertex Pharmaceuticals Incorporated | Sposoby i związki pośrednie |
| 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 |
| AU2006301966A1 (en) | 2005-10-11 | 2007-04-19 | Array Biopharma, Inc. | Compounds and methods for inhibiting hepatitis C viral replication |
| EP2392589A3 (en) | 2005-11-11 | 2012-06-20 | Vertex Pharmaceuticals Incorporated | Hepatitis C virus variants |
| US7705138B2 (en) | 2005-11-11 | 2010-04-27 | Vertex Pharmaceuticals Incorporated | Hepatitis C virus variants |
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-
2001
- 2001-04-17 CN CNA2009100067369A patent/CN101580536A/zh active Pending
- 2001-04-17 EP EP01927142A patent/EP1274724A2/en not_active Withdrawn
- 2001-04-17 CN CNA2006101537103A patent/CN1935833A/zh active Pending
- 2001-04-17 PE PE2001000348A patent/PE20011288A1/es not_active Application Discontinuation
- 2001-04-17 JP JP2001578418A patent/JP4748912B2/ja not_active Expired - Fee Related
- 2001-04-17 NZ NZ521456A patent/NZ521456A/en unknown
- 2001-04-17 CN CN01810566A patent/CN1432022A/zh active Pending
- 2001-04-17 MX MXPA02010375A patent/MXPA02010375A/es active IP Right Grant
- 2001-04-17 WO PCT/US2001/012530 patent/WO2001081325A2/en not_active Ceased
- 2001-04-17 RU RU2002131163/04A patent/RU2002131163A/ru not_active Application Discontinuation
- 2001-04-17 CA CA002406532A patent/CA2406532A1/en not_active Abandoned
- 2001-04-17 KR KR1020027013965A patent/KR20020097220A/ko not_active Withdrawn
- 2001-04-17 SK SK1495-2002A patent/SK14952002A3/sk not_active Application Discontinuation
- 2001-04-17 AR ARP010101794A patent/AR030558A1/es unknown
- 2001-04-17 PL PL01358591A patent/PL358591A1/xx not_active Application Discontinuation
- 2001-04-17 BR BR0110104-8A patent/BR0110104A/pt not_active IP Right Cessation
- 2001-04-17 HK HK03100478.8A patent/HK1048479A1/zh unknown
- 2001-04-17 HU HU0302957A patent/HUP0302957A2/hu unknown
- 2001-04-17 CZ CZ20023473A patent/CZ20023473A3/cs unknown
- 2001-04-17 US US09/836,636 patent/US6914122B2/en not_active Expired - Fee Related
- 2001-04-17 AU AU2001253621A patent/AU2001253621A1/en not_active Abandoned
- 2001-04-17 IL IL15193501A patent/IL151935A0/xx unknown
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2002
- 2002-10-04 ZA ZA200208014A patent/ZA200208014B/en unknown
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