JP5580814B2 - 3環式インドール誘導体およびその使用方法 - Google Patents
3環式インドール誘導体およびその使用方法 Download PDFInfo
- Publication number
- JP5580814B2 JP5580814B2 JP2011513649A JP2011513649A JP5580814B2 JP 5580814 B2 JP5580814 B2 JP 5580814B2 JP 2011513649 A JP2011513649 A JP 2011513649A JP 2011513649 A JP2011513649 A JP 2011513649A JP 5580814 B2 JP5580814 B2 JP 5580814B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- pharmaceutically acceptable
- mmol
- acceptable salt
- additional antiviral
- 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.)
- Active
Links
- 0 C*=Cc(c(F)c1)cc(I)c1F Chemical compound C*=Cc(c(F)c1)cc(I)c1F 0.000 description 18
- JAWXCWWSKOEMRC-UHFFFAOYSA-N CC(C(c1cc2c3OCCc3ccc2cc1)=O)=C Chemical compound CC(C(c1cc2c3OCCc3ccc2cc1)=O)=C JAWXCWWSKOEMRC-UHFFFAOYSA-N 0.000 description 1
- XRBJETTVICDTGU-UHFFFAOYSA-N CC(C)(C)OC(N(C(OC(C)(C)C)=O)c1nc2ccccc2c(C)n1)=O Chemical compound CC(C)(C)OC(N(C(OC(C)(C)C)=O)c1nc2ccccc2c(C)n1)=O XRBJETTVICDTGU-UHFFFAOYSA-N 0.000 description 1
- INTWEJLLLSSBIK-CCEZHUSRSA-N CC(C)(C)S/N=N/C(C(C)(C)C=C1)C=C1C(O)=O Chemical compound CC(C)(C)S/N=N/C(C(C)(C)C=C1)C=C1C(O)=O INTWEJLLLSSBIK-CCEZHUSRSA-N 0.000 description 1
- SKWCBGYXUIIOMZ-UHFFFAOYSA-N CC(C)C1=CC2=CCCC=C2N=C1Cl Chemical compound CC(C)C1=CC2=CCCC=C2N=C1Cl SKWCBGYXUIIOMZ-UHFFFAOYSA-N 0.000 description 1
- VPOYOQMWKWPTIN-UHFFFAOYSA-N CC(C)c(c(F)c1)cc2c1NCN2 Chemical compound CC(C)c(c(F)c1)cc2c1NCN2 VPOYOQMWKWPTIN-UHFFFAOYSA-N 0.000 description 1
- CBICQVIAVZYAIA-UHFFFAOYSA-N CC(C)c(cc(cccc1)c1n1)c1Cl Chemical compound CC(C)c(cc(cccc1)c1n1)c1Cl CBICQVIAVZYAIA-UHFFFAOYSA-N 0.000 description 1
- SMZJTBRBXXASED-UHFFFAOYSA-N CC(C1)C=Cc(cc2)c1c(C=C1C(OC)=O)c2C1=C Chemical compound CC(C1)C=Cc(cc2)c1c(C=C1C(OC)=O)c2C1=C SMZJTBRBXXASED-UHFFFAOYSA-N 0.000 description 1
- QQVHJZNMBSCSNV-UHFFFAOYSA-N CC1(C)C=CC(F)=CC1F Chemical compound CC1(C)C=CC(F)=CC1F QQVHJZNMBSCSNV-UHFFFAOYSA-N 0.000 description 1
- QUUFHRSTBTZWMA-UHFFFAOYSA-N Cc(c(F)c1)cc(C#N)c1F Chemical compound Cc(c(F)c1)cc(C#N)c1F QUUFHRSTBTZWMA-UHFFFAOYSA-N 0.000 description 1
- VDKSZOIFBWOEFF-UHFFFAOYSA-N Cc(c(F)c1)cc(C(N)=[IH])c1NN Chemical compound Cc(c(F)c1)cc(C(N)=[IH])c1NN VDKSZOIFBWOEFF-UHFFFAOYSA-N 0.000 description 1
- QLFLTNBMONMJMI-UHFFFAOYSA-N Cc(c(F)c1)cc(I)c1F Chemical compound Cc(c(F)c1)cc(I)c1F QLFLTNBMONMJMI-UHFFFAOYSA-N 0.000 description 1
- GPUIJBWDORWOPA-UHFFFAOYSA-N Cc(c(F)c1)cc2c1N=CNC2=O Chemical compound Cc(c(F)c1)cc2c1N=CNC2=O GPUIJBWDORWOPA-UHFFFAOYSA-N 0.000 description 1
- YJTXGEOAXOZANY-UHFFFAOYSA-N Cc(cc(c(NN1)c2)C1=O)c2F Chemical compound Cc(cc(c(NN1)c2)C1=O)c2F YJTXGEOAXOZANY-UHFFFAOYSA-N 0.000 description 1
- HNKNXHBNGNMERD-UHFFFAOYSA-N Nc(c1c2[o]cc1)ccc2N=O Chemical compound Nc(c1c2[o]cc1)ccc2N=O HNKNXHBNGNMERD-UHFFFAOYSA-N 0.000 description 1
- MBVFRSJFKMJRHA-UHFFFAOYSA-N O=Cc(cc1)c2[o]ccc2c1F Chemical compound O=Cc(cc1)c2[o]ccc2c1F MBVFRSJFKMJRHA-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Virology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Molecular Biology (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
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 JP2011524359A5 (https=) | 2012-06-07 |
| JP5580814B2 true 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 |
|---|---|---|---|---|
| AU2007339382B2 (en) | 2006-12-22 | 2013-05-02 | Merck Sharp & Dohme Llc | 4,5-ring annulated indole derivatives for treating or preventing of HCV and related viral infections |
| KR102127406B1 (ko) | 2012-09-20 | 2020-06-29 | 유디씨 아일랜드 리미티드 | 전자 응용을 위한 아자디벤조푸란 |
| ES2688147T3 (es) | 2014-03-21 | 2018-10-31 | Bristol-Myers Squibb Company | Compuestos de 6H-furo[2,3-e]indol para el tratamiento de la 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 |
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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 |
| 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 |
| US5017380A (en) * | 1986-07-02 | 1991-05-21 | Shionogi & Co., Ltd. | Gelatin hard capsule containing crystalline hydrate of oral cephalosporin |
| 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 |
| AP1019A (en) | 1996-10-18 | 2001-10-16 | Vertex Pharma | Inhibitors of serinre proteases, particularly hepatitis C virus NS3 protease. |
| GB9623908D0 (en) | 1996-11-18 | 1997-01-08 | Hoffmann La Roche | Amino acid derivatives |
| EP1012180B1 (en) | 1997-08-11 | 2004-12-01 | Boehringer Ingelheim (Canada) Ltd. | Hepatitis c inhibitor peptide analogues |
| FR2768146B1 (fr) | 1997-09-05 | 2000-05-05 | Oreal | Nouveaux composes de la famille des indole-carboxyliques et leur utilisation |
| ES2317900T3 (es) * | 2000-04-05 | 2009-05-01 | Schering Corporation | Inhibidores de serina proteasa ns3 macrociclicos del virus de la hepatitis c que comprenden fragmentos n-ciclicas p2. |
| AU2001253621A1 (en) * | 2000-04-19 | 2001-11-07 | Schering Corporation | Macrocyclic NS3-serine protease inhibitors of hepatitis C virus comprising alkyl and aryl alanine P2 moieties |
| 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 |
| CN1498224A (zh) * | 2000-07-21 | 2004-05-19 | ���鹫˾ | 用作丙型肝炎病毒ns3-丝氨酸蛋白酶抑制剂的新型肽 |
| SK742003A3 (en) * | 2000-07-21 | 2003-06-03 | Schering Corp | Novel peptides as NS3-serine protease inhibitors of hepatitis C virus |
| PL366068A1 (en) | 2000-10-10 | 2005-01-24 | Smithkline Beecham Corporation | Substituted indoles, pharmaceutical compositions containing such indoles and their use as ppar-gamma binding agents |
| AU3659102A (en) * | 2000-12-12 | 2002-06-24 | Schering Corp | Diaryl peptides as ns3-serine protease inhibitors of hepatits c virus |
| WO2002050030A2 (en) * | 2000-12-18 | 2002-06-27 | Eli Lilly And Company | Cycloalkylfused [g]-indole compounds as spla2-inhibitors in the treatment of inflammatory diseases |
| US7626026B2 (en) | 2001-02-22 | 2009-12-01 | University Of Bradford | Pyrrolo-indole and pyrrolo-quinoline derivatives as prodrugs for tumour treatment |
| 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 |
| CN1832939B (zh) | 2003-05-30 | 2010-04-28 | 杰明X医药品加拿大公司 | 用于治疗癌症或病毒病的三杂环化合物、组合物和方法 |
| GB0323845D0 (en) | 2003-10-10 | 2003-11-12 | Angeletti P Ist Richerche Bio | Chemical compounds,compositions and uses |
| PE20050925A1 (es) * | 2003-11-10 | 2005-11-29 | Schering Corp | Anticuerpo recombinante humanizado anti-interleuquina 10 |
| EP1714427A1 (de) | 2004-02-09 | 2006-10-25 | Hörmann KG Antriebstechnik | Torantriebssystem mit seriellem bus für kommunikation der komponenten |
| CN103102389A (zh) | 2004-02-27 | 2013-05-15 | 默沙东公司 | 作为丙型肝炎病毒ns3丝氨酸蛋白酶抑制剂的硫化合物 |
| JP2007526320A (ja) * | 2004-03-01 | 2007-09-13 | バイロファーマ・インコーポレイテッド | ピラノインドール誘導体およびc型肝炎ウイルス感染症または疾患の治療のためのその使用 |
| US20050249702A1 (en) * | 2004-05-06 | 2005-11-10 | Schering Corporation | (1R,2S,5S)-N-[(1S)-3-amino-1-(cyclobutylmethyl)-2,3-dioxopropyl]-3-[(2S)-2-[[[(1,1-dimethylethyl)amino]carbonyl]amino]-3,3-dimethyl-1-oxobutyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide as inhibitor of hepatitis C virus NS3/NS4a serine protease |
| EP1604988A1 (en) | 2004-05-18 | 2005-12-14 | Sanofi-Aventis Deutschland GmbH | Pyridazinone derivatives, methods for producing them and their use as pharmaceuticals |
| WO2007084413A2 (en) | 2004-07-14 | 2007-07-26 | Ptc Therapeutics, Inc. | Methods for treating hepatitis c |
| US7153848B2 (en) | 2004-08-09 | 2006-12-26 | Bristol-Myers Squibb Company | Inhibitors of HCV replication |
| MX2007003371A (es) | 2004-09-23 | 2007-05-07 | Wyeth Corp | Derivados de carbazol y ciclopentaindol para tratar infeccion con virus de hepatitis c. |
| DE102004047272A1 (de) | 2004-09-24 | 2006-04-06 | Schering Ag | Inhibitoren der löslichen Adenylatzyklase |
| EP1807403A2 (en) | 2004-10-26 | 2007-07-18 | Istituto di Richerche di Biologia Molecolare P. Angeletti S.p.A. | 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 |
| GB0518390D0 (en) | 2005-09-09 | 2005-10-19 | Angeletti P Ist Richerche Bio | Therapeutic compounds |
| US7482360B2 (en) | 2005-09-23 | 2009-01-27 | Schering Corporation | Fused tetracyclic mGluR1 antagonists as therapeutic agents |
| JP2009523732A (ja) | 2006-01-13 | 2009-06-25 | ピーティーシー セラピューティクス,インコーポレーテッド | C型肝炎の治療方法 |
| EP1981524A2 (en) * | 2006-02-09 | 2008-10-22 | Schering Corporation | Combinations comprising hcv protease inhibitor(s) and hcv polymerase inhibitor(s), and methods of treatment related thereto |
| AU2007339382B2 (en) * | 2006-12-22 | 2013-05-02 | Merck Sharp & Dohme Llc | 4,5-ring annulated indole derivatives for treating or preventing of HCV and related viral infections |
| EP2081922B1 (en) * | 2006-12-22 | 2012-02-01 | Schering Corporation | 5,6-Ring annulated indole derivatives and use thereof |
| JP5211068B2 (ja) * | 2006-12-22 | 2013-06-12 | メルク・シャープ・アンド・ドーム・コーポレーション | Hcvおよび関連するウイルス疾患の治療または予防のための4,5−環インドール誘導体 |
| EP2197884A2 (en) * | 2007-08-29 | 2010-06-23 | Schering Corporation | Tetracyclic indole derivatives and their use for treating or preventing viral infections |
| WO2009032116A1 (en) * | 2007-08-29 | 2009-03-12 | Schering Corporation | 2, 3-substituted indole derivatives for treating viral infections |
| ATE541845T1 (de) * | 2007-08-29 | 2012-02-15 | Schering Corp | 2,3-substituierte azaindolderivate zur behandlung von virusinfektionen |
| TW200924780A (en) * | 2007-08-29 | 2009-06-16 | Schering Corp | 2-carboxy substituted indole derivatives and methods of use thereof |
| CA2705587A1 (en) * | 2007-11-16 | 2009-05-22 | Schering Corporation | 3-aminosulfonyl substituted indole derivatives and methods of use thereof |
| MX2010005356A (es) * | 2007-11-16 | 2010-05-27 | Schering Corp | Derivados de indol 3-heterociclico sustituidos y metodos de uso de los mismos. |
-
2009
- 2009-06-10 AR ARP090102091A patent/AR072088A1/es not_active Application Discontinuation
- 2009-06-10 CA CA2727620A patent/CA2727620A1/en not_active Abandoned
- 2009-06-10 MX MX2010013630A patent/MX2010013630A/es active IP Right Grant
- 2009-06-10 WO PCT/US2009/046822 patent/WO2009152200A1/en not_active Ceased
- 2009-06-10 JP JP2011513649A patent/JP5580814B2/ja active Active
- 2009-06-10 US US12/997,654 patent/US8901139B2/en active Active
- 2009-06-10 EP EP09763490.1A patent/EP2303893B1/en not_active Not-in-force
- 2009-06-10 CN CN200980131569.9A patent/CN102159579B/zh active Active
- 2009-06-11 TW TW098119583A patent/TW201011030A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP2011524359A (ja) | 2011-09-01 |
| EP2303893A1 (en) | 2011-04-06 |
| AR072088A1 (es) | 2010-08-04 |
| CA2727620A1 (en) | 2009-12-17 |
| CN102159579B (zh) | 2015-03-25 |
| TW201011030A (en) | 2010-03-16 |
| US8901139B2 (en) | 2014-12-02 |
| US20110189127A1 (en) | 2011-08-04 |
| WO2009152200A1 (en) | 2009-12-17 |
| MX2010013630A (es) | 2010-12-21 |
| EP2303893B1 (en) | 2016-12-07 |
| CN102159579A (zh) | 2011-08-17 |
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