JP2011524359A5 - - Google Patents
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- Publication number
- JP2011524359A5 JP2011524359A5 JP2011513649A JP2011513649A JP2011524359A5 JP 2011524359 A5 JP2011524359 A5 JP 2011524359A5 JP 2011513649 A JP2011513649 A JP 2011513649A JP 2011513649 A JP2011513649 A JP 2011513649A JP 2011524359 A5 JP2011524359 A5 JP 2011524359A5
- Authority
- JP
- Japan
- Prior art keywords
- additional antiviral
- antiviral agent
- composition
- pharmaceutically acceptable
- solvate
- 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
Links
- 239000003443 antiviral agent Substances 0.000 claims description 50
- 150000001875 compounds Chemical class 0.000 claims description 33
- 239000008194 pharmaceutical composition Substances 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 30
- 239000012453 solvate Substances 0.000 claims description 30
- 108010050904 Interferons Proteins 0.000 claims description 28
- 102000014150 Interferons Human genes 0.000 claims description 28
- 229940079322 interferon Drugs 0.000 claims description 27
- 150000002148 esters Chemical class 0.000 claims description 26
- 229940002612 prodrug Drugs 0.000 claims description 26
- 239000000651 prodrug Substances 0.000 claims description 26
- 238000010276 construction Methods 0.000 claims description 24
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- 229940122604 HCV protease inhibitor Drugs 0.000 claims description 12
- 239000003112 inhibitor Substances 0.000 claims description 12
- 229960000517 boceprevir Drugs 0.000 claims description 8
- LHHCSNFAOIFYRV-DOVBMPENSA-N boceprevir Chemical group O=C([C@@H]1[C@@H]2[C@@H](C2(C)C)CN1C(=O)[C@@H](NC(=O)NC(C)(C)C)C(C)(C)C)NC(C(=O)C(N)=O)CC1CCC1 LHHCSNFAOIFYRV-DOVBMPENSA-N 0.000 claims description 8
- 230000001419 dependent effect Effects 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 229960002935 telaprevir Drugs 0.000 claims description 8
- BBAWEDCPNXPBQM-GDEBMMAJSA-N telaprevir Chemical compound N([C@H](C(=O)N[C@H](C(=O)N1C[C@@H]2CCC[C@@H]2[C@H]1C(=O)N[C@@H](CCC)C(=O)C(=O)NC1CC1)C(C)(C)C)C1CCCCC1)C(=O)C1=CN=CC=N1 BBAWEDCPNXPBQM-GDEBMMAJSA-N 0.000 claims description 8
- 108010017101 telaprevir Proteins 0.000 claims description 8
- 229940124683 HCV polymerase inhibitor Drugs 0.000 claims description 6
- 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 6
- 208000036142 Viral infection Diseases 0.000 claims description 6
- 229940123627 Viral replication inhibitor Drugs 0.000 claims description 6
- 229960000329 ribavirin Drugs 0.000 claims description 6
- 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 6
- 230000009385 viral infection Effects 0.000 claims description 6
- 230000003612 virological effect Effects 0.000 claims description 6
- 102100040018 Interferon alpha-2 Human genes 0.000 claims description 4
- 108010079944 Interferon-alpha2b Proteins 0.000 claims description 4
- 229940118555 Viral entry inhibitor Drugs 0.000 claims description 4
- 241000700605 Viruses Species 0.000 claims description 4
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 4
- 230000000692 anti-sense effect Effects 0.000 claims description 4
- 238000009175 antibody therapy Methods 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 239000000137 peptide hydrolase inhibitor Substances 0.000 claims description 4
- -1 t- butyl Chemical group 0.000 claims description 4
- 229940021747 therapeutic vaccine Drugs 0.000 claims description 4
- 229940124158 Protease/peptidase inhibitor Drugs 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 239000002955 immunomodulating agent Substances 0.000 claims description 2
- 229940121354 immunomodulator Drugs 0.000 claims description 2
- 208000015181 infectious disease Diseases 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 239000002777 nucleoside Substances 0.000 claims description 2
- 150000003833 nucleoside derivatives Chemical class 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
- 230000010076 replication Effects 0.000 claims description 2
- 210000002845 virion Anatomy 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 18
- 108060004795 Methyltransferase Proteins 0.000 claims 1
- 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 claims 1
- 229940047124 interferons Drugs 0.000 claims 1
- 238000000034 method Methods 0.000 description 17
- 0 CC=CC=C([C@@](C(C(O)=O)N(CC(C[C@@]1C=NC)=C(*)C=C1C=C)c1c2)c1c1[o]ccc1c2F)C(C=*)=O Chemical compound CC=CC=C([C@@](C(C(O)=O)N(CC(C[C@@]1C=NC)=C(*)C=C1C=C)c1c2)c1c1[o]ccc1c2F)C(C=*)=O 0.000 description 3
- 229940121759 Helicase inhibitor Drugs 0.000 description 1
- 229940123066 Polymerase inhibitor Drugs 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000002584 immunomodulator Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6134408P | 2008-06-13 | 2008-06-13 | |
| US61/061,344 | 2008-06-13 | ||
| PCT/US2009/046822 WO2009152200A1 (en) | 2008-06-13 | 2009-06-10 | Tricyclic indole derivatives and methods of use thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011524359A JP2011524359A (ja) | 2011-09-01 |
| JP2011524359A5 true JP2011524359A5 (https=) | 2012-06-07 |
| JP5580814B2 JP5580814B2 (ja) | 2014-08-27 |
Family
ID=40943627
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011513649A Active JP5580814B2 (ja) | 2008-06-13 | 2009-06-10 | ３環式インドール誘導体およびその使用方法 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8901139B2 (https=) |
| EP (1) | EP2303893B1 (https=) |
| JP (1) | JP5580814B2 (https=) |
| CN (1) | CN102159579B (https=) |
| AR (1) | AR072088A1 (https=) |
| CA (1) | CA2727620A1 (https=) |
| MX (1) | MX2010013630A (https=) |
| TW (1) | TW201011030A (https=) |
| WO (1) | WO2009152200A1 (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8557848B2 (en) | 2006-12-22 | 2013-10-15 | Merck Sharp & Dohme Corp. | 4,5-ring annulated indole derivatives for treating or preventing of HCV and related viral infections |
| WO2014044722A1 (en) | 2012-09-20 | 2014-03-27 | Basf Se | Azadibenzofurans for electronic applications |
| WO2015143257A1 (en) * | 2014-03-21 | 2015-09-24 | Bristol-Myers Squibb Company | 6h-furo[2,3-e]indole compounds for the treatment of hepatitis c |
| WO2015160636A1 (en) | 2014-04-16 | 2015-10-22 | Merck Sharp & Dohme Corp. | Factor ixa inhibitors |
| WO2018151239A1 (ja) * | 2017-02-17 | 2018-08-23 | 第一三共株式会社 | ３，６－ジヒドロ－２Ｈ－フロ［２，３－ｅ］インドール化合物 |
| CN116063310A (zh) * | 2022-12-23 | 2023-05-05 | 齐鲁工业大学 | 一种呋喃并[3,4-b]吲哚衍生物及其合成方法 |
Family Cites Families (53)
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| DE648639C (de) | 1935-05-19 | 1937-08-05 | I G Farbenindustrie Akt Ges | Verfahren zur Darstellung von Dipyrrolen |
| US3632805A (en) | 1967-12-08 | 1972-01-04 | Sumitomo Chemical Co | Process for producing 1-aminoalkyl-benzodiazepine derivatives |
| AU575854B2 (en) | 1983-10-04 | 1988-08-11 | Shionogi & Co., Ltd. | 7beta-(carboxyalkenamido) cephalosporins |
| US5017380A (en) | 1986-07-02 | 1991-05-21 | Shionogi & Co., Ltd. | Gelatin hard capsule containing crystalline hydrate of oral cephalosporin |
| NZ220764A (en) | 1986-07-02 | 1989-09-27 | Shionogi & Co | Crystalline form of 7beta((z)-2-(2-aminothiazol-4-yl)-4- carboxybut-2-enoylamino)-3-cephem-4-carboxylic acid and pharmaceutical compositions |
| CA2038925A1 (en) | 1990-03-26 | 1991-09-27 | Takashi Sohda | Indole derivatives, their production and use |
| JPH04149429A (ja) | 1990-10-12 | 1992-05-22 | Fuji Photo Film Co Ltd | ハロゲン化銀カラー反転写真感光材料およびそれを用いた画像形成方法 |
| IT1278077B1 (it) | 1995-05-25 | 1997-11-17 | Angeletti P Ist Richerche Bio | Metodologia per riprodurre in vitro le attivita' di rna polimerasi rna-dipendente e di nucleotidiltransferasi terminale codificate dal |
| US5922757A (en) | 1996-09-30 | 1999-07-13 | The Regents Of The University Of California | Treatment and prevention of hepatic disorders |
| KR100509388B1 (ko) | 1996-10-18 | 2005-08-23 | 버텍스 파마슈티칼스 인코포레이티드 | 세린 프로테아제, 특히 간염 ｃ 바이러스 ｎｓ３ 프로테아제의 저해제 |
| GB9623908D0 (en) | 1996-11-18 | 1997-01-08 | Hoffmann La Roche | Amino acid derivatives |
| ES2234144T3 (es) | 1997-08-11 | 2005-06-16 | Boehringer Ingelheim (Canada) Ltd. | Analogos de peptidos inhibidores de la hepatitis c. |
| FR2768146B1 (fr) | 1997-09-05 | 2000-05-05 | Oreal | Nouveaux composes de la famille des indole-carboxyliques et leur utilisation |
| AR029903A1 (es) | 2000-04-05 | 2003-07-23 | Schering Corp | Inhibidores macrociclicos de la ns3-serina proteasa, del virus de la hepatitis c, que comprenden partes p2 n-ciclicas, composiciones farmaceuticas y utilizacion de los mismos para la manufactura de un medicamento |
| CN101580536A (zh) | 2000-04-19 | 2009-11-18 | 先灵公司 | 含有烷基和芳基丙氨酸p2部分的丙型肝炎病毒的大环ns3-丝氨酸蛋白酶抑制剂 |
| KR20030081297A (ko) | 2000-07-21 | 2003-10-17 | 쉐링 코포레이션 | Ｃ형 간염 바이러스의 ｎｓ3-세린 프로테아제억제제로서의 신규한 펩티드 |
| DK1385870T3 (da) | 2000-07-21 | 2010-07-05 | Schering Corp | Peptider som inhibitorer af NS3-serinprotease fra hepatitis C-virus |
| AR029851A1 (es) | 2000-07-21 | 2003-07-16 | Dendreon Corp | Nuevos peptidos como inhibidores de ns3-serina proteasa del virus de hepatitis c |
| AR034127A1 (es) | 2000-07-21 | 2004-02-04 | Schering Corp | Imidazolidinonas como inhibidores de ns3-serina proteasa del virus de hepatitis c, composicion farmaceutica, un metodo para su preparacion, y el uso de las mismas para la manufactura de un medicamento |
| AU2002211901A1 (en) | 2000-10-10 | 2002-04-22 | Smithkline Beecham Corporation | Substituted indoles, pharmaceutical compositions containing such indoles and their use as PPAR-gamma binding agents |
| KR20030091946A (ko) | 2000-12-12 | 2003-12-03 | 쉐링 코포레이션 | Ｃ형 간염 바이러스의 ｎｓ3-세린 프로테아제억제제로서의 디아릴 펩티드 |
| JP2004518658A (ja) | 2000-12-18 | 2004-06-24 | イーライ・リリー・アンド・カンパニー | 新規なｓＰＬＡ２インヒビター |
| ES2299560T3 (es) | 2001-02-22 | 2008-06-01 | University Of Bradford | Derivados de pirrolindol y de pirroloquinolina como profarmacos para el tratamiento de tumores. |
| EP2335700A1 (en) | 2001-07-25 | 2011-06-22 | Boehringer Ingelheim (Canada) Ltd. | Hepatitis C virus polymerase inhibitors with a heterobicylic structure |
| WO2004035571A1 (en) | 2002-10-15 | 2004-04-29 | Rigel Pharmaceuticals, Inc. | Substituted indoles and their use as hcv inhibitors |
| US20050075331A1 (en) | 2003-10-06 | 2005-04-07 | Pratt John K. | Anti-infective agents |
| ES2382377T3 (es) | 2003-05-30 | 2012-06-07 | Gemin X Pharmaceuticals Canada Inc. | Compuestos triheterocíclicos, composiciones, y métodos para tratar cáncer |
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| WO2005076529A1 (de) | 2004-02-09 | 2005-08-18 | Hörmann KG Antriebstechnik | Torantriebssystem mit seriellem bus für kommunikation der komponenten |
| DE602005021760D1 (de) | 2004-02-27 | 2010-07-22 | Schering Corp | Schwefelverbindungen als inhibitoren der ns3-serinprotease des hepatitis-c-virus |
| US20070219212A1 (en) * | 2004-03-01 | 2007-09-20 | Condon Stephen M | Pyranouidole Derivatives and the Use Thereof for the Treatment of Hepatitis C Virus Infection or Disease |
| AR049635A1 (es) | 2004-05-06 | 2006-08-23 | Schering Corp | (1r,2s,5s)-n-((1s)-3-amino-1-(ciclobutilmetil)-2,3-dioxopropil)-3-((2s)-2-((((1,1-dimetiletil)amino)carbonil)amino)-3,3-dimetil-1-oxobutil)-6,6-dimetil-3-azabiciclo(3.1.0)hexan-2-carboxamida como inhibidor de la ns3/ns4a serina proteasa del virus de la hepatitis c |
| EP1604988A1 (en) | 2004-05-18 | 2005-12-14 | Sanofi-Aventis Deutschland GmbH | Pyridazinone derivatives, methods for producing them and their use as pharmaceuticals |
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| WO2006046039A2 (en) | 2004-10-26 | 2006-05-04 | Istituto Di Ricerche Di Biologia Molecolare P Angeletti Spa | Tetracyclic indole derivatives as antiviral agents |
| US20110104109A1 (en) | 2005-07-13 | 2011-05-05 | Frank Bennett | Tetracyclic indole derivatives and their use for treating or preventing viral infections |
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| US7482360B2 (en) | 2005-09-23 | 2009-01-27 | Schering Corporation | Fused tetracyclic mGluR1 antagonists as therapeutic agents |
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| CN101611025A (zh) | 2006-12-22 | 2009-12-23 | 先灵公司 | 5,6-环化的吲哚衍生物及其使用方法 |
| WO2008082488A1 (en) | 2006-12-22 | 2008-07-10 | Schering Corporation | 4, 5-ring annulated indole derivatives for treating or preventing of hcv and related viral infections |
| US8557848B2 (en) * | 2006-12-22 | 2013-10-15 | Merck Sharp & Dohme Corp. | 4,5-ring annulated indole derivatives for treating or preventing of HCV and related viral infections |
| WO2009032116A1 (en) | 2007-08-29 | 2009-03-12 | Schering Corporation | 2, 3-substituted indole derivatives for treating viral infections |
| AU2008295483B2 (en) * | 2007-08-29 | 2013-11-21 | Merck Sharp & Dohme Corp. | Tetracyclic indole derivatives and their use for treating or preventing viral infections |
| EP2408761B1 (en) | 2007-08-29 | 2014-01-01 | Merck Sharp & Dohme Corp. | Substituted indole derivatives and methods of use thereof |
| ATE541845T1 (de) | 2007-08-29 | 2012-02-15 | Schering Corp | 2,3-substituierte azaindolderivate zur behandlung von virusinfektionen |
| MX2010005356A (es) | 2007-11-16 | 2010-05-27 | Schering Corp | Derivados de indol 3-heterociclico sustituidos y metodos de uso de los mismos. |
| US8377928B2 (en) | 2007-11-16 | 2013-02-19 | Merck Sharp & Dohme Corp. | 3-aminosulfonyl substituted indole derivatives and methods of use thereof |
-
2009
- 2009-06-10 MX MX2010013630A patent/MX2010013630A/es active IP Right Grant
- 2009-06-10 AR ARP090102091A patent/AR072088A1/es not_active Application Discontinuation
- 2009-06-10 EP EP09763490.1A patent/EP2303893B1/en not_active Not-in-force
- 2009-06-10 JP JP2011513649A patent/JP5580814B2/ja active Active
- 2009-06-10 CN CN200980131569.9A patent/CN102159579B/zh active Active
- 2009-06-10 CA CA2727620A patent/CA2727620A1/en not_active Abandoned
- 2009-06-10 WO PCT/US2009/046822 patent/WO2009152200A1/en not_active Ceased
- 2009-06-10 US US12/997,654 patent/US8901139B2/en active Active
- 2009-06-11 TW TW098119583A patent/TW201011030A/zh unknown