JP2011521911A5 - - Google Patents
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- Publication number
- JP2011521911A5 JP2011521911A5 JP2011509693A JP2011509693A JP2011521911A5 JP 2011521911 A5 JP2011521911 A5 JP 2011521911A5 JP 2011509693 A JP2011509693 A JP 2011509693A JP 2011509693 A JP2011509693 A JP 2011509693A JP 2011521911 A5 JP2011521911 A5 JP 2011521911A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- cycloalkyl
- heterocyclyl
- aryl
- ring
- 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.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 claims 50
- 125000000753 cycloalkyl group Chemical group 0.000 claims 36
- 125000000623 heterocyclic group Chemical group 0.000 claims 29
- 125000003118 aryl group Chemical group 0.000 claims 22
- 125000003545 alkoxy group Chemical group 0.000 claims 20
- 125000003710 aryl alkyl group Chemical group 0.000 claims 19
- 125000005843 halogen group Chemical group 0.000 claims 18
- 125000001424 substituent group Chemical group 0.000 claims 15
- 150000001875 compounds Chemical class 0.000 claims 14
- 125000004438 haloalkoxy group Chemical group 0.000 claims 14
- 125000001188 haloalkyl group Chemical group 0.000 claims 14
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 12
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 12
- 229910052757 nitrogen Inorganic materials 0.000 claims 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims 11
- 229910052739 hydrogen Inorganic materials 0.000 claims 11
- 239000001257 hydrogen Substances 0.000 claims 11
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 11
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 10
- 125000003342 alkenyl group Chemical group 0.000 claims 9
- 108010050904 Interferons Proteins 0.000 claims 8
- 102000014150 Interferons Human genes 0.000 claims 8
- 229940079322 interferon Drugs 0.000 claims 8
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 7
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 7
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 6
- 125000002619 bicyclic group Chemical group 0.000 claims 6
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 229910052717 sulfur Chemical group 0.000 claims 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 5
- 125000005842 heteroatom Chemical group 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 239000001301 oxygen Chemical group 0.000 claims 5
- 239000011593 sulfur Chemical group 0.000 claims 5
- 108010047761 Interferon-alpha Proteins 0.000 claims 4
- 102000006992 Interferon-alpha Human genes 0.000 claims 4
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
- 102100040018 Interferon alpha-2 Human genes 0.000 claims 2
- 108010079944 Interferon-alpha2b Proteins 0.000 claims 2
- 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 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 2
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 229960000329 ribavirin Drugs 0.000 claims 2
- 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 2
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims 1
- -1 and —NR a R b Chemical group 0.000 claims 1
- 125000005243 carbonyl alkyl group Chemical group 0.000 claims 1
- 125000004181 carboxyalkyl group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 0 *C(NS(C1CC1)=O)=O Chemical compound *C(NS(C1CC1)=O)=O 0.000 description 3
- LDPFQEGHGCYLLU-MRVPVSSYSA-N C=C(C1)C(CNC2)=C2[C@@H]1F Chemical compound C=C(C1)C(CNC2)=C2[C@@H]1F LDPFQEGHGCYLLU-MRVPVSSYSA-N 0.000 description 1
- PRYMNWPBNFZBJU-UHFFFAOYSA-N C=[O]c1cc(-c2ccc[s]2)cc(-c2ccccc2)n1 Chemical compound C=[O]c1cc(-c2ccc[s]2)cc(-c2ccccc2)n1 PRYMNWPBNFZBJU-UHFFFAOYSA-N 0.000 description 1
- FMEVIWVRSLFAET-RYUDHWBXSA-N CC(C)(C)c1c[s]c(N[C@@H](C=C)C(N(CCC2)[C@@H]2C=O)=O)n1 Chemical compound CC(C)(C)c1c[s]c(N[C@@H](C=C)C(N(CCC2)[C@@H]2C=O)=O)n1 FMEVIWVRSLFAET-RYUDHWBXSA-N 0.000 description 1
- BXGSJQULVHQVKB-UHFFFAOYSA-N CC(NS(C1CC1)(=O)=O)=O Chemical compound CC(NS(C1CC1)(=O)=O)=O BXGSJQULVHQVKB-UHFFFAOYSA-N 0.000 description 1
- HLCXNVMIINTAOG-UHFFFAOYSA-N CC1(CC1)C(N)=O Chemical compound CC1(CC1)C(N)=O HLCXNVMIINTAOG-UHFFFAOYSA-N 0.000 description 1
- YXHCKZZLEVVUBZ-MRXNPFEDSA-N C[C@H](CNC(CNc1cc(C)cc(C)n1)=O)OCC(N(Cc1ccc2)Cc1c2F)=O Chemical compound C[C@H](CNC(CNc1cc(C)cc(C)n1)=O)OCC(N(Cc1ccc2)Cc1c2F)=O YXHCKZZLEVVUBZ-MRXNPFEDSA-N 0.000 description 1
- ARWVSUOYVJFDTO-NSHDSACASA-N Cc1cc(C)nc(NCC(N(CCC2)[C@@H]2C(N)=O)=O)c1 Chemical compound Cc1cc(C)nc(NCC(N(CCC2)[C@@H]2C(N)=O)=O)c1 ARWVSUOYVJFDTO-NSHDSACASA-N 0.000 description 1
- ZVRAHWAZBQUVSP-UHFFFAOYSA-N NC(C1CC1)O Chemical compound NC(C1CC1)O ZVRAHWAZBQUVSP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5347708P | 2008-05-15 | 2008-05-15 | |
| US61/053,477 | 2008-05-15 | ||
| PCT/US2009/043920 WO2009140475A1 (en) | 2008-05-15 | 2009-05-14 | Hepatitis c virus inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2011521911A JP2011521911A (ja) | 2011-07-28 |
| JP2011521911A5 true JP2011521911A5 (enExample) | 2012-06-07 |
Family
ID=41017064
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011509693A Pending JP2011521911A (ja) | 2008-05-15 | 2009-05-14 | Ｃ型肝炎ウイルス阻害剤 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20090285774A1 (enExample) |
| EP (1) | EP2280958A1 (enExample) |
| JP (1) | JP2011521911A (enExample) |
| CN (1) | CN102099353A (enExample) |
| WO (1) | WO2009140475A1 (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8202996B2 (en) | 2007-12-21 | 2012-06-19 | Bristol-Myers Squibb Company | Crystalline forms of N-(tert-butoxycarbonyl)-3-methyl-L-valyl-(4R)-4-((7-chloro-4-methoxy-1-isoquinolinyl)oxy)-N- ((1R,2S)-1-((cyclopropylsulfonyl)carbamoyl)-2-vinylcyclopropyl)-L-prolinamide |
| WO2009142842A2 (en) | 2008-04-15 | 2009-11-26 | Intermune, Inc. | Novel macrocyclic inhibitors of hepatitis c virus replication |
| US8207341B2 (en) | 2008-09-04 | 2012-06-26 | Bristol-Myers Squibb Company | Process or synthesizing substituted isoquinolines |
| UY32099A (es) | 2008-09-11 | 2010-04-30 | Enanta Pharm Inc | Inhibidores macrocíclicos de serina proteasas de hepatitis c |
| AR075584A1 (es) | 2009-02-27 | 2011-04-20 | Intermune Inc | COMPOSICIONES TERAPEUTICAS QUE COMPRENDEN beta-D-2'-DESOXI-2'-FLUORO-2'-C-METILCITIDINA Y UN DERIVADO DE ACIDO ISOINDOL CARBOXILICO Y SUS USOS. COMPUESTO. |
| EP2429568B1 (en) | 2009-05-13 | 2016-08-17 | Enanta Pharmaceuticals, Inc. | Macrocyclic compounds as hepatitis c virus inhibitors |
| US9193740B2 (en) * | 2009-10-19 | 2015-11-24 | Enanta Pharmaceuticals, Inc. | Bismacrocyclic compounds as hepatitis C virus inhibitors |
| EP2655362A1 (en) | 2010-12-22 | 2013-10-30 | Abbvie Inc. | Hepatitis c inhibitors and uses thereof |
| KR20140003521A (ko) | 2010-12-30 | 2014-01-09 | 이난타 파마슈티칼스, 인코포레이티드 | 페난트리딘 매크로사이클릭 ｃ형 간염 세린 프로테아제 억제제 |
| MX2013007677A (es) | 2010-12-30 | 2013-07-30 | Abbvie Inc | Inhibidores macrociclicos de serina proteasa de hepatitis. |
| US8957203B2 (en) | 2011-05-05 | 2015-02-17 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US10201584B1 (en) | 2011-05-17 | 2019-02-12 | Abbvie Inc. | Compositions and methods for treating HCV |
| US8691757B2 (en) | 2011-06-15 | 2014-04-08 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| TWI589576B (zh) | 2011-07-15 | 2017-07-01 | 諾華公司 | 氮雜－雙環二芳基醚之鹽類及製造彼等或其前驅物之方法 |
| MX355102B (es) | 2012-01-11 | 2018-04-05 | Abbvie Ireland Unlimited Co | Procesos para hacer los inhibidores de la proteasa del hcv. |
| HRP20161694T1 (hr) | 2012-10-19 | 2017-03-10 | Bristol-Myers Squibb Company | 9-metil supstituirani heksadekahidrociklopropa(e)pirolo (1,2-a)(1,4) diazaciklopentadecinil karbamat derivati kao ne-strukturalni 3 (ns3) proteazni inhibitori za liječenje infekcija virusom hepatitisa c |
| US9643999B2 (en) | 2012-11-02 | 2017-05-09 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| WO2014070964A1 (en) | 2012-11-02 | 2014-05-08 | Bristol-Myers Squibb Company | Hepatitis c virus inhibitors |
| EP2914598B1 (en) | 2012-11-02 | 2017-10-18 | Bristol-Myers Squibb Company | Hepatitis c virus inhibitors |
| US9409943B2 (en) | 2012-11-05 | 2016-08-09 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US9580463B2 (en) | 2013-03-07 | 2017-02-28 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| WO2015103490A1 (en) | 2014-01-03 | 2015-07-09 | Abbvie, Inc. | Solid antiviral dosage forms |
| CN103965286B (zh) * | 2014-04-22 | 2017-11-03 | 南京安赛莱医药科技有限公司 | 丙型肝炎病毒（hcv）ns3蛋白酶抑制剂 |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0475255A3 (en) * | 1990-09-12 | 1993-04-14 | F. Hoffmann-La Roche Ag | Process for the preparation of optically pure (s)-alpha-((tert-butylsulfonyl)methyl)hydro cinnamic acid |
| US6323180B1 (en) * | 1998-08-10 | 2001-11-27 | Boehringer Ingelheim (Canada) Ltd | Hepatitis C inhibitor tri-peptides |
| CN100391967C (zh) * | 2000-11-20 | 2008-06-04 | 布里斯托尔-迈尔斯斯奎布公司 | 丙型肝炎三肽抑制剂 |
| MY140680A (en) * | 2002-05-20 | 2010-01-15 | Bristol Myers Squibb Co | Hepatitis c virus inhibitors |
| US20060199773A1 (en) * | 2002-05-20 | 2006-09-07 | Sausker Justin B | Crystalline forms of (1R,2S)-N-[(1,1-dimethylethoxy)carbonyl]-3-methyl-L-valyl-(4R)-4-[(6-methoxy-1-isoquinolinyl)oxy]-L-prolyl-1-amino-N-(cyclopropylsulfonyl)-2-ethenyl-cyclopropanecarboxamide, monopotassium salt |
| US7601709B2 (en) * | 2003-02-07 | 2009-10-13 | Enanta Pharmaceuticals, Inc. | Macrocyclic hepatitis C serine protease inhibitors |
| JP4733023B2 (ja) * | 2003-04-16 | 2011-07-27 | ブリストル−マイヤーズ スクイブ カンパニー | Ｃ型肝炎ウイルスの大環状イソキノリンペプチド阻害剤 |
| JP4654239B2 (ja) * | 2004-03-15 | 2011-03-16 | 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型肝炎ウィルス感染症の治療に適した大環状ジペプチドの調製方法 |
| WO2006000085A1 (en) * | 2004-06-28 | 2006-01-05 | Boehringer Ingelheim International Gmbh | Hepatitis c inhibitor peptide analogs |
| US7601686B2 (en) * | 2005-07-11 | 2009-10-13 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| TW200738742A (en) * | 2005-07-14 | 2007-10-16 | Gilead Sciences Inc | Antiviral compounds |
| US7825152B2 (en) * | 2006-04-11 | 2010-11-02 | Novartis Ag | Organic compounds and their uses |
| US8268776B2 (en) * | 2006-06-06 | 2012-09-18 | Enanta Pharmaceuticals, Inc. | Macrocylic oximyl hepatitis C protease inhibitors |
| US7635683B2 (en) * | 2006-08-04 | 2009-12-22 | Enanta Pharmaceuticals, Inc. | Quinoxalinyl tripeptide hepatitis C virus inhibitors |
| US7582605B2 (en) * | 2006-08-11 | 2009-09-01 | Enanta Pharmaceuticals, Inc. | Phosphorus-containing hepatitis C serine protease inhibitors |
| US7605126B2 (en) * | 2006-08-11 | 2009-10-20 | Enanta Pharmaceuticals, Inc. | Acylaminoheteroaryl hepatitis C virus protease inhibitors |
| US7772180B2 (en) * | 2006-11-09 | 2010-08-10 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US20080279821A1 (en) * | 2007-04-26 | 2008-11-13 | Deqiang Niu | Arylpiperidinyl and arylpyrrolidinyl macrocyclic hepatitis c serine protease inhibitors |
| EP2160392A2 (en) * | 2007-05-03 | 2010-03-10 | Intermune, Inc. | Novel macrocyclic inhibitors of hepatitis c virus replication |
| BRPI0811447A2 (pt) * | 2007-05-10 | 2014-10-29 | Intermune Inc | Compostos, composição farmacêutica e métodos de inibição da atividade da protease ns3/ns4, de tratamento da fibrose hepática e de intensificação da função hepática num indivíduo tendo infecção de vírus da hepatite c. |
| US20090047252A1 (en) * | 2007-06-29 | 2009-02-19 | Gilead Sciences, Inc. | Antiviral compounds |
| MX2010006738A (es) * | 2007-12-21 | 2010-10-15 | Avila Therapeutics Inc | Inhibidores de proteasa del virus de la hepatitis c (hcv) y usos de los mismos. |
| US8202996B2 (en) * | 2007-12-21 | 2012-06-19 | Bristol-Myers Squibb Company | Crystalline forms of N-(tert-butoxycarbonyl)-3-methyl-L-valyl-(4R)-4-((7-chloro-4-methoxy-1-isoquinolinyl)oxy)-N- ((1R,2S)-1-((cyclopropylsulfonyl)carbamoyl)-2-vinylcyclopropyl)-L-prolinamide |
-
2009
- 2009-05-13 US US12/465,142 patent/US20090285774A1/en not_active Abandoned
- 2009-05-14 EP EP09747557A patent/EP2280958A1/en not_active Withdrawn
- 2009-05-14 JP JP2011509693A patent/JP2011521911A/ja active Pending
- 2009-05-14 CN CN2009801276783A patent/CN102099353A/zh active Pending
- 2009-05-14 WO PCT/US2009/043920 patent/WO2009140475A1/en not_active Ceased
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