JP5230052B2 - フラビウイルスおよびペスチウイルス治療のための方法および組成物 - Google Patents
フラビウイルスおよびペスチウイルス治療のための方法および組成物 Download PDFInfo
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- JP5230052B2 JP5230052B2 JP2002500895A JP2002500895A JP5230052B2 JP 5230052 B2 JP5230052 B2 JP 5230052B2 JP 2002500895 A JP2002500895 A JP 2002500895A JP 2002500895 A JP2002500895 A JP 2002500895A JP 5230052 B2 JP5230052 B2 JP 5230052B2
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- alkyl
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| JP4294870B2 (ja) * | 1998-08-10 | 2009-07-15 | インデニックス ファーマシューティカルズ リミティド | B型肝炎の治療のためのβ−L−2’−デオキシ−ヌクレオシド |
| WO2001067772A2 (en) * | 2000-03-09 | 2001-09-13 | Videoshare, Inc. | Sharing a streaming video |
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| DZ3487A1 (fr) * | 2001-01-22 | 2002-07-25 | Merck Sharp & Dohme | Derives de nucleoside comme inhibiteurs de l'arn polymerase virale d'arn-dependant |
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| US7217815B2 (en) * | 2002-01-17 | 2007-05-15 | Valeant Pharmaceuticals North America | 2-beta -modified-6-substituted adenosine analogs and their use as antiviral agents |
| AU2003209045B2 (en) * | 2002-02-13 | 2006-12-14 | Isis Pharmaceuticals, Inc. | Methods of inhibiting orthopoxvirus replication with nucleoside compounds |
| US7247621B2 (en) * | 2002-04-30 | 2007-07-24 | Valeant Research & Development | Antiviral phosphonate compounds and methods therefor |
| RU2004135392A (ru) * | 2002-05-06 | 2005-06-27 | Дженелэбс Текнолоджиз, Инк. (Us) | Производные нуклеозидов для лечения инфекции, вызываемой вирусом гепатита с |
| CA2488484A1 (en) * | 2002-06-27 | 2004-01-08 | Merck & Co., Inc. | Nucleoside derivatives as inhibitors of rna-dependent rna viral polymerase |
| EP2799442A1 (en) * | 2002-06-28 | 2014-11-05 | IDENIX Pharmaceuticals, Inc. | Modified 2' and 3' -nucleoside prodrugs for treating flaviridae infections |
| MXPA04012779A (es) | 2002-06-28 | 2005-08-19 | Idenix Cayman Ltd | Profarmacos de 2'- y 3'-nucleosido para tratar infecciones por flaviviridae. |
| US7608600B2 (en) | 2002-06-28 | 2009-10-27 | Idenix Pharmaceuticals, Inc. | Modified 2′ and 3′-nucleoside prodrugs for treating Flaviviridae infections |
| KR20050035194A (ko) | 2002-06-28 | 2005-04-15 | 이데닉스 (케이만) 리미티드 | 플라비비리다에 감염 치료용 2'-c-메틸-3'-o-l-발린에스테르 리보푸라노실 사이티딘 |
| RU2437892C2 (ru) * | 2002-06-28 | 2011-12-27 | Айденикс (Кайман) Лимитед | Модифицированные 2- и 3-нуклеозиды и их применение для получения лекарственного средства, обладающего ингибирующей активностью в отношении вируса гепатита с |
| CN101172993A (zh) * | 2002-06-28 | 2008-05-07 | 埃迪尼克斯(开曼)有限公司 | 用于治疗黄病毒感染的2′-c-甲基-3′-o-l-缬氨酸酯核糖呋喃基胞苷 |
| EP1556399A4 (en) * | 2002-07-16 | 2007-09-26 | Merck & Co Inc | Nucleoside derivatives as inhibitors of RNA-dependent viral RNA polymerase |
| WO2004009020A2 (en) | 2002-07-24 | 2004-01-29 | Merck & Co., Inc. | Pyrrolopyrimidine thionucleoside analogs as antivirals |
| US20040067877A1 (en) | 2002-08-01 | 2004-04-08 | Schinazi Raymond F. | 2', 3'-Dideoxynucleoside analogues for the treatment or prevention of Flaviviridae infections |
| JP2006507235A (ja) | 2002-08-01 | 2006-03-02 | フアーマセツト・インコーポレイテツド | フラビウイルス科ウイルス感染治療のためのビシクロ[4.2.1]ノナン系を有する化合物 |
| CA2503730C (en) | 2002-10-31 | 2011-10-18 | Metabasis Therapeutics, Inc. | Cytarabine monophosphate prodrugs |
| ES2624353T3 (es) | 2002-11-15 | 2017-07-13 | Idenix Pharmaceuticals Llc | 2'-Metil nucleósidos en combinación con interferón y mutación de Flaviviridae |
| US7034167B2 (en) | 2002-12-06 | 2006-04-25 | Merck & Co., Inc. | Process to ribofuranose sugar derivatives as intermediates to branched-chain nucleosides |
| AU2003300901A1 (en) | 2002-12-12 | 2004-06-30 | Idenix (Cayman) Limited | Process for the production of 2'-branched nucleosides |
| RU2005123395A (ru) * | 2002-12-23 | 2006-01-27 | Айденикс (Кайман) Лимитед (Ky) | Способ получения 3-нуклеозидных пролекарств |
| AR043006A1 (es) | 2003-02-12 | 2005-07-13 | Merck & Co Inc | Proceso para preparar ribonucleosidos ramificados |
| JP2006524227A (ja) * | 2003-03-28 | 2006-10-26 | ファーマセット,インク. | フラビウイルス科ウイルス感染の治療のための化合物 |
| US20040259934A1 (en) * | 2003-05-01 | 2004-12-23 | Olsen David B. | Inhibiting Coronaviridae viral replication and treating Coronaviridae viral infection with nucleoside compounds |
| FI2604620T4 (fi) | 2003-05-30 | 2024-09-11 | Gilead Pharmasset Llc | Modifioituja fluorinoituja nukleosidianalogeja |
| ATE478886T1 (de) * | 2003-07-25 | 2010-09-15 | Idenix Pharmaceuticals Inc | Purin nucleoside für die behandlung von durch flavividrae verursachten krankheiten, einschliesslich hepatitis c |
| WO2005018330A1 (en) * | 2003-08-18 | 2005-03-03 | Pharmasset, Inc. | Dosing regimen for flaviviridae therapy |
| JP2007504152A (ja) | 2003-08-27 | 2007-03-01 | ビオタ, インコーポレイテッド | 治療剤としての新規三環ヌクレオシドまたはヌクレオチド |
| GB0500020D0 (en) | 2005-01-04 | 2005-02-09 | Novartis Ag | Organic compounds |
| US20050182252A1 (en) * | 2004-02-13 | 2005-08-18 | Reddy K. R. | Novel 2'-C-methyl nucleoside derivatives |
| JP5055564B2 (ja) | 2004-06-15 | 2012-10-24 | メルク・シャープ・エンド・ドーム・コーポレイション | Rna依存性rnaウイルスポリメラーゼの阻害剤としてのc−プリンヌクレオシド類似体 |
| EP1912643A2 (en) * | 2004-06-23 | 2008-04-23 | Idenix (Cayman) Limited | 5-aza-7-deazapurine derivatives for treating infections with flaviviridae |
| CN1972696B (zh) * | 2004-06-24 | 2010-08-11 | 默沙东公司 | 用于治疗rna依赖性rna病毒感染的核苷氨基磷酸芳基酯 |
| CN101023094B (zh) | 2004-07-21 | 2011-05-18 | 法莫赛特股份有限公司 | 烷基取代的2-脱氧-2-氟代-d-呋喃核糖基嘧啶和嘌呤及其衍生物的制备 |
| BRPI0515279A (pt) | 2004-09-14 | 2008-07-15 | Pharmasset Inc | preparação de ribofuranosil pirimidinas e purinas 2'fluoro-2'-alquil- substituìdas ou outras opcionalmente substituìdas e seus derivados |
| US7524831B2 (en) | 2005-03-02 | 2009-04-28 | Schering Corporation | Treatments for Flaviviridae virus infection |
| EP1858889A1 (en) | 2005-03-08 | 2007-11-28 | Biota Scientific Management Pty. Ltd. | Bicyclic nucleosides and nucleotides as therapeutic agents |
| US20090156545A1 (en) * | 2005-04-01 | 2009-06-18 | Hostetler Karl Y | Substituted Phosphate Esters of Nucleoside Phosphonates |
| AU2006242475B2 (en) | 2005-05-02 | 2011-07-07 | Merck Sharp & Dohme Corp. | HCV NS3 protease inhibitors |
| MX2007016068A (es) | 2005-06-17 | 2008-03-10 | Novartis Ag | Uso de sanglifehrina en hcv. |
| AR057456A1 (es) | 2005-07-20 | 2007-12-05 | Merck & Co Inc | Inhibidores de la proteasa ns3 del vhc |
| US8278322B2 (en) | 2005-08-01 | 2012-10-02 | Merck Sharp & Dohme Corp. | HCV NS3 protease inhibitors |
| AR056191A1 (es) * | 2005-08-23 | 2007-09-26 | Idenix Phatmaceuticals Inc | Anillo de nucleosidos de siete miembros como inhibidores de la replica viral, metodos para su sintesis, composiciones farmaceuticas que los contienen y su uso en el tratamiento de infecciones con virus de la familia flaviviridae |
| WO2007044468A2 (en) * | 2005-10-05 | 2007-04-19 | The Cbr Institute For Biomedical Research, Inc. | Method to treat flavivirus infection with sirna |
| KR101238461B1 (ko) | 2005-12-09 | 2013-03-05 | 길리어드 파마셋 엘엘씨 | 항바이러스성 뉴클레오시드 |
| EP1976382B1 (en) | 2005-12-23 | 2013-04-24 | IDENIX Pharmaceuticals, Inc. | Process for preparing a synthetic intermediate for preparation of branched nucleosides |
| US8895531B2 (en) | 2006-03-23 | 2014-11-25 | Rfs Pharma Llc | 2′-fluoronucleoside phosphonates as antiviral agents |
| JP2009532411A (ja) * | 2006-04-04 | 2009-09-10 | エフ.ホフマン−ラ ロシュ アーゲー | Hcv治療のための3’,5’−ジ−o−アシル化ヌクレオシド |
| EP2007789B1 (en) | 2006-04-11 | 2015-05-20 | Novartis AG | Spirocyclic HCV/HIV inhibitors and their uses |
| GB0609492D0 (en) | 2006-05-15 | 2006-06-21 | Angeletti P Ist Richerche Bio | Therapeutic agents |
| US8058260B2 (en) * | 2006-05-22 | 2011-11-15 | Xenoport, Inc. | 2′-C-methyl-ribofuranosyl cytidine prodrugs, pharmaceutical compositions and uses thereof |
| GB0612423D0 (en) | 2006-06-23 | 2006-08-02 | Angeletti P Ist Richerche Bio | Therapeutic agents |
| RU2421461C2 (ru) | 2006-10-10 | 2011-06-20 | Фармассет, Инк. | Способ получения рибофуранозил-пиримидиновых нуклеозидов |
| MX2009003452A (es) | 2006-10-10 | 2009-04-14 | Medivir Ab | Inhibidores nucleosidicos del vhc. |
| US8309540B2 (en) | 2006-10-24 | 2012-11-13 | Merck Sharp & Dohme Corp. | HCV NS3 protease inhibitors |
| US8138164B2 (en) | 2006-10-24 | 2012-03-20 | Merck Sharp & Dohme Corp. | HCV NS3 protease inhibitors |
| WO2008051477A2 (en) | 2006-10-24 | 2008-05-02 | Merck & Co., Inc. | Hcv ns3 protease inhibitors |
| US8377874B2 (en) | 2006-10-27 | 2013-02-19 | Merck Sharp & Dohme Corp. | HCV NS3 protease inhibitors |
| JP5268927B2 (ja) | 2006-10-27 | 2013-08-21 | メルク・シャープ・アンド・ドーム・コーポレーション | Hcvns3プロテアーゼ阻害剤 |
| BRPI0718714B8 (pt) | 2006-11-09 | 2021-05-25 | Hoffmann La Roche | arilamidas substituídas por tiazol e oxazol, seu uso e composição farmacêutica que as compreende |
| GB0623493D0 (en) | 2006-11-24 | 2007-01-03 | Univ Cardiff | Chemical compounds |
| US7897737B2 (en) | 2006-12-05 | 2011-03-01 | Lasergen, Inc. | 3′-OH unblocked, nucleotides and nucleosides, base modified with photocleavable, terminating groups and methods for their use in DNA sequencing |
| GB0625283D0 (en) | 2006-12-19 | 2007-01-24 | Cyclacel Ltd | Combination |
| CA2672250C (en) | 2006-12-20 | 2013-04-30 | Ian Stansfield | Antiviral indoles |
| GB0625345D0 (en) | 2006-12-20 | 2007-01-31 | Angeletti P Ist Richerche Bio | Therapeutic compounds |
| GB0625349D0 (en) | 2006-12-20 | 2007-01-31 | Angeletti P Ist Richerche Bio | Therapeutic compounds |
| US7951789B2 (en) | 2006-12-28 | 2011-05-31 | Idenix Pharmaceuticals, Inc. | Compounds and pharmaceutical compositions for the treatment of viral infections |
| WO2008085508A2 (en) | 2007-01-05 | 2008-07-17 | Merck & Co., Inc. | Nucleoside aryl phosphoramidates for the treatment of rna-dependent rna viral infection |
| DK2114980T3 (da) * | 2007-01-12 | 2012-09-24 | Biocryst Pharm Inc | Antivirale nukleosidanaloger |
| PT2144604E (pt) | 2007-02-28 | 2011-10-19 | Conatus Pharmaceuticals Inc | Métodos para o tratamento da hepatite c viral crónica utilizando ro-113-0830 |
| SI2308514T1 (sl) | 2007-03-23 | 2013-09-30 | To-Bbb Holding B.V. | Konjugati za prenos zdravila preko krvno-moĹľganske pregrade |
| US7964580B2 (en) | 2007-03-30 | 2011-06-21 | Pharmasset, Inc. | Nucleoside phosphoramidate prodrugs |
| CN101754970B (zh) | 2007-07-17 | 2013-07-10 | P.安杰莱蒂分子生物学研究所 | 用于治疗丙型肝炎的大环吲哚衍生物 |
| US8927569B2 (en) | 2007-07-19 | 2015-01-06 | Merck Sharp & Dohme Corp. | Macrocyclic compounds as antiviral agents |
| PT2234976E (pt) | 2007-12-17 | 2013-07-11 | Hoffmann La Roche | Novas arilamidas substituídas por pirazol |
| WO2009077371A1 (en) | 2007-12-17 | 2009-06-25 | F. Hoffmann-La Roche Ag | Tetrazole-substituted arylamide derivatives and their use as p2x3 and/or p2x2/3 purinergic receptor antagonists |
| JP5318882B2 (ja) | 2007-12-17 | 2013-10-16 | エフ.ホフマン−ラ ロシュ アーゲー | 新規なイミダゾール置換アリールアミド |
| ES2542245T3 (es) | 2007-12-17 | 2015-08-03 | F. Hoffmann-La Roche Ag | Derivados de arilamida sustituido con triazol y su utilización como antagonistas del receptor purinérgico P2x3 y/o P2x2/3 |
| EP2265626B1 (en) * | 2008-03-18 | 2019-05-15 | LCB Pharma Inc | Nucleotide analogues with quaternary carbon stereogenic centers and methods of use |
| TW200946541A (en) | 2008-03-27 | 2009-11-16 | Idenix Pharmaceuticals Inc | Solid forms of an anti-HIV phosphoindole compound |
| HRP20150359T1 (hr) | 2008-04-23 | 2015-05-22 | Gilead Sciences, Inc. | 1'-supstituirani karba-nukleozidni analozi za antivirusnu terapiju |
| JP2011518882A (ja) | 2008-04-28 | 2011-06-30 | メルク・シャープ・エンド・ドーム・コーポレイション | Hcvns3プロテアーゼ阻害剤 |
| EP2307002B1 (en) | 2008-06-09 | 2013-01-02 | Cyclacel Limited | Combinations of sapacitabine or cndac with dna methyltransferase inhibitors such as decitabine and procaine |
| US8173621B2 (en) * | 2008-06-11 | 2012-05-08 | Gilead Pharmasset Llc | Nucleoside cyclicphosphates |
| EA201100001A3 (ru) | 2008-06-11 | 2013-03-29 | Лейзеджен, Инк. | Нуклеотиды и нуклеозиды и методы их использования в секвенировании днк |
| EP2476690A1 (en) * | 2008-07-02 | 2012-07-18 | IDENIX Pharmaceuticals, Inc. | Compounds and pharmaceutical compositions for the treatment of viral infections |
| EP2313102A2 (en) | 2008-07-03 | 2011-04-27 | Biota Scientific Management | Bycyclic nucleosides and nucleotides as therapeutic agents |
| PE20110212A1 (es) | 2008-07-22 | 2011-04-10 | Merck Sharp & Dohme | (1aR, 5S, 8S, 10R, 22aR)-5-TERT-BUTIL-N-{(1R, 2S)-1-{[(CICLOPROPILSULFONIL) AMINO] CARBONIL}-2-VINILCICLOPROPIL}-14-METOXI-3,6-DIOXO-1, 1a, 3, 4, 5, 6, 9, 10, 18, 19, 20, 21, 22, 22a-TETRADECAHIDRO-8H-7, 10-METANOCICLOPROPA[18, 19] [1, 10, 3, 6] DIOXADIAZACICLONONADECINO[11, 12-b] QUINOXALIN-8-CARBOXAMIDA COMO INHIBIDOR DE LA PROTEASA HCV NS3 |
| MX2011002071A (es) | 2008-08-29 | 2011-04-05 | Boehringer Ingelheim Vetmed | Vacuna para el virus del nilo occidental. |
| US8716262B2 (en) | 2008-12-23 | 2014-05-06 | Gilead Pharmasset Llc | Nucleoside phosphoramidates |
| AR074977A1 (es) | 2008-12-23 | 2011-03-02 | Pharmasset Inc | Sintesis de nucleosidos de purina |
| CN102753563A (zh) | 2008-12-23 | 2012-10-24 | 吉利德制药有限责任公司 | 核苷类似物 |
| MX2011007364A (es) * | 2009-01-09 | 2012-02-28 | Univ Cardiff | Derivados de fosforamidato de compuestos de nuecleosido de guanosina para tratamiento de infecciones virales. |
| WO2010082050A1 (en) | 2009-01-16 | 2010-07-22 | Istituto Di Ricerche Di Biologia Molecolare P. Angeletti S.P.A. | Macrocyclic and 7-aminoalkyl-substituted benzoxazocines for treatment of hepatitis c infections |
| GB0900914D0 (en) | 2009-01-20 | 2009-03-04 | Angeletti P Ist Richerche Bio | Antiviral agents |
| WO2010101967A2 (en) | 2009-03-04 | 2010-09-10 | Idenix Pharmaceuticals, Inc. | Phosphothiophene and phosphothiazole hcv polymerase inhibitors |
| EA201190178A1 (ru) * | 2009-03-20 | 2012-06-29 | Алиос Биофарма, Инк. | Замещённые нуклеозидные и нуклеотидные аналоги |
| US20110182850A1 (en) | 2009-04-10 | 2011-07-28 | Trixi Brandl | Organic compounds and their uses |
| US8512690B2 (en) | 2009-04-10 | 2013-08-20 | Novartis Ag | Derivatised proline containing peptide compounds as protease inhibitors |
| TWI583692B (zh) | 2009-05-20 | 2017-05-21 | 基利法瑪席特有限責任公司 | 核苷磷醯胺 |
| US8618076B2 (en) | 2009-05-20 | 2013-12-31 | Gilead Pharmasset Llc | Nucleoside phosphoramidates |
| WO2010135520A1 (en) * | 2009-05-20 | 2010-11-25 | Chimerix, Inc. | Compounds, compositions and methods for treating viral infection |
| WO2010149634A1 (en) | 2009-06-22 | 2010-12-29 | F. Hoffmann-La Roche Ag | Novel indole, indazole and benzimidazole arylamides as p2x3 and/or p2x2/3 antagonists |
| JP5476467B2 (ja) | 2009-06-22 | 2014-04-23 | エフ.ホフマン−ラ ロシュ アーゲー | 新規なビフェニルピリジンアミドおよびフェニルピリジンアミド |
| ES2593405T3 (es) | 2009-06-22 | 2016-12-09 | F. Hoffmann-La Roche Ag | Nuevas arilamidas sustituidas por benzoxazolona |
| WO2011014487A1 (en) | 2009-07-30 | 2011-02-03 | Merck Sharp & Dohme Corp. | Hepatitis c virus ns3 protease inhibitors |
| JP2013501068A (ja) | 2009-08-05 | 2013-01-10 | アイディニックス ファーマシューティカルズ インコーポレイテッド | 大環状セリンプロテアーゼ阻害剤 |
| EP2480559B1 (en) | 2009-09-21 | 2013-07-03 | Gilead Sciences, Inc. | Processes and intermediates for the preparation of 1'-cyano-carbanucleoside analogs |
| EP2499493A1 (en) | 2009-11-14 | 2012-09-19 | F. Hoffmann-La Roche AG | Biomarkers for predicting rapid response to hcv treatment |
| US20110117055A1 (en) | 2009-11-19 | 2011-05-19 | Macdonald James E | Methods of Treating Hepatitis C Virus with Oxoacetamide Compounds |
| SG181104A1 (en) | 2009-12-02 | 2012-07-30 | Hoffmann La Roche | Biomarkers for predicting sustained response to hcv treatment |
| CN102822175A (zh) | 2009-12-18 | 2012-12-12 | 埃迪尼克斯医药公司 | 5,5-稠合的亚芳基或亚杂芳基丙型肝炎病毒抑制剂 |
| PT3290428T (pt) | 2010-03-31 | 2021-12-27 | Gilead Pharmasset Llc | Comprimido compreendendo 2-(((s)-(((2r,3r,4r,5r)-5-(2,4-dioxo-3,4-dihidropirimidin-1-(2h)-il)¿4¿fluoro¿3¿hidroxi¿4¿metiltetrahidrofuran¿2¿il)metoxi) (fenoxi)fosforil)amino)propanoato de (s)- isopropil cristalino |
| US8563530B2 (en) | 2010-03-31 | 2013-10-22 | Gilead Pharmassel LLC | Purine nucleoside phosphoramidate |
| TWI515000B (zh) | 2010-04-01 | 2016-01-01 | 伊迪尼克製藥公司 | 用於治療病毒感染之化合物及醫藥組合物 |
| ES2524398T3 (es) | 2010-07-19 | 2014-12-09 | Gilead Sciences, Inc. | Métodos para la preparación de profármacos de fosforoamidato diastereoméricamente puros |
| ME01924B (me) | 2010-07-22 | 2015-05-20 | Gilead Sciences Inc | Metode i jedinjenja za lečenje infekcija izazvanih Paramyxoviridae virusom |
| JP6012605B2 (ja) | 2010-09-22 | 2016-10-25 | アリオス バイオファーマ インク. | 置換されたヌクレオチドアナログ |
| CN103179966B (zh) | 2010-10-08 | 2017-03-15 | 诺瓦提斯公司 | 磺酰胺ns3抑制剂的维生素e制剂 |
| US8841275B2 (en) | 2010-11-30 | 2014-09-23 | Gilead Pharmasset Llc | 2′-spiro-nucleosides and derivatives thereof useful for treating hepatitis C virus and dengue virus infections |
| WO2012080050A1 (en) | 2010-12-14 | 2012-06-21 | F. Hoffmann-La Roche Ag | Solid forms of a phenoxybenzenesulfonyl compound |
| EP2658857B1 (en) * | 2010-12-29 | 2016-11-02 | Inhibitex, Inc. | Substituted purine nucleosides, phosphoroamidate and phosphorodiamidate derivatives for treatment of viral infections |
| AR085352A1 (es) | 2011-02-10 | 2013-09-25 | Idenix Pharmaceuticals Inc | Inhibidores macrociclicos de serina proteasa, sus composiciones farmaceuticas y su uso para tratar infecciones por hcv |
| EP2772266B1 (en) | 2011-03-14 | 2019-07-31 | Boehringer Ingelheim Animal Health USA Inc. | Equine Rhinitis vaccine |
| US20120252721A1 (en) | 2011-03-31 | 2012-10-04 | Idenix Pharmaceuticals, Inc. | Methods for treating drug-resistant hepatitis c virus infection with a 5,5-fused arylene or heteroarylene hepatitis c virus inhibitor |
| CN103842369A (zh) | 2011-03-31 | 2014-06-04 | 埃迪尼克斯医药公司 | 用于治疗病毒感染的化合物和药物组合物 |
| EP2696679B1 (en) | 2011-04-13 | 2017-08-02 | Merck Sharp & Dohme Corp. | 2'-cyano substituted nucleoside derivatives and methods of use thereof for the treatment of viral diseases |
| WO2012142075A1 (en) | 2011-04-13 | 2012-10-18 | Merck Sharp & Dohme Corp. | 2'-azido substituted nucleoside derivatives and methods of use thereof for the treatment of viral diseases |
| JP2014515023A (ja) | 2011-04-13 | 2014-06-26 | メルク・シャープ・アンド・ドーム・コーポレーション | 2’−置換ヌクレオシド誘導体およびウイルス疾患の処置のためのその使用方法 |
| EP2696878B1 (en) | 2011-04-14 | 2019-07-10 | Cyclacel Limited | Dosage regimen for sapacitabine and decitabine in combination for treating acute myeloid leukemia |
| CN102775458B (zh) * | 2011-05-09 | 2015-11-25 | 中国人民解放军军事医学科学院毒物药物研究所 | β-D-(2’R)-2’-脱氧—2’-氟-2’-C-甲基胞苷衍生物的制备及用途 |
| EP2731433A4 (en) | 2011-07-13 | 2014-12-31 | Merck Sharp & Dohme | 5'-SUBSTITUTED NUCLEOSIDE ANALOGA AND METHOD FOR THEIR USE FOR THE TREATMENT OF VIRUS DISEASES |
| WO2013009735A1 (en) | 2011-07-13 | 2013-01-17 | Merck Sharp & Dohme Corp. | 5'-substituted nucleoside derivatives and methods of use thereof for the treatment of viral diseases |
| AU2012308900A1 (en) | 2011-09-12 | 2013-05-09 | Idenix Pharmaceuticals, Inc. | Compounds and pharmaceutical compositions for the treatment of viral infections |
| US9403863B2 (en) | 2011-09-12 | 2016-08-02 | Idenix Pharmaceuticals Llc | Substituted carbonyloxymethylphosphoramidate compounds and pharmaceutical compositions for the treatment of viral infections |
| JP6196972B2 (ja) | 2011-09-13 | 2017-09-13 | レーザーゲン インコーポレイテッド | 5−メトキシ3’−oh非遮断高速光開裂性末端ヌクレオチドおよび核酸配列決定のための方法 |
| KR101991298B1 (ko) | 2011-09-16 | 2019-06-21 | 길리애드 파마셋 엘엘씨 | Hcv 치료 방법 |
| TW201331221A (zh) | 2011-10-14 | 2013-08-01 | Idenix Pharmaceuticals Inc | 嘌呤核苷酸化合物類之經取代的3’,5’-環磷酸酯及用於治療病毒感染之醫藥組成物 |
| EP2780026B1 (en) | 2011-11-15 | 2019-10-23 | Merck Sharp & Dohme Corp. | Hcv ns3 protease inhibitors |
| US8889159B2 (en) | 2011-11-29 | 2014-11-18 | Gilead Pharmasset Llc | Compositions and methods for treating hepatitis C virus |
| WO2013082476A1 (en) | 2011-11-30 | 2013-06-06 | Emory University | Antiviral jak inhibitors useful in treating or preventing retroviral and other viral infections |
| WO2013096680A1 (en) | 2011-12-22 | 2013-06-27 | Alios Biopharma, Inc. | Substituted phosphorothioate nucleotide analogs |
| US20140356325A1 (en) | 2012-01-12 | 2014-12-04 | Ligand Pharmaceuticals Incorporated | Novel 2'-c-methyl nucleoside derivative compounds |
| WO2013133927A1 (en) | 2012-02-13 | 2013-09-12 | Idenix Pharmaceuticals, Inc. | Pharmaceutical compositions of 2'-c-methyl-guanosine, 5'-[2-[(3-hydroxy-2,2-dimethyl-1-oxopropyl)thio]ethyl n-(phenylmethyl)phosphoramidate] |
| US8673926B2 (en) | 2012-02-14 | 2014-03-18 | University Of Georgia Research Foundation, Inc. | Spiro[2.4]heptanes for treatment of flaviviridae infections |
| WO2013142124A1 (en) | 2012-03-21 | 2013-09-26 | Vertex Pharmaceuticals Incorporated | Solid forms of a thiophosphoramidate nucleotide prodrug |
| EP2827876A4 (en) | 2012-03-22 | 2015-10-28 | Alios Biopharma Inc | PHARMACEUTICAL COMBINATIONS WITH A THIONUCLEOTIDE ANALOG |
| EP2852604B1 (en) | 2012-05-22 | 2017-04-12 | Idenix Pharmaceuticals LLC | 3',5'-cyclic phosphoramidate prodrugs for hcv infection |
| US9296778B2 (en) | 2012-05-22 | 2016-03-29 | Idenix Pharmaceuticals, Inc. | 3′,5′-cyclic phosphate prodrugs for HCV infection |
| HK1203514A1 (en) | 2012-05-22 | 2015-10-30 | Idenix Pharmaceuticals Llc | D-amino acid compounds for liver disease |
| PT2861611T (pt) | 2012-05-25 | 2016-10-11 | Janssen Sciences Ireland Uc | Nucleósidos de espirooxetano de uracilo |
| US9206412B2 (en) | 2012-05-31 | 2015-12-08 | Colorado State University Research Foundation | Thioxothiazolidine inhibitors |
| WO2014052638A1 (en) | 2012-09-27 | 2014-04-03 | Idenix Pharmaceuticals, Inc. | Esters and malonates of sate prodrugs |
| CN104936970A (zh) | 2012-10-08 | 2015-09-23 | 埃迪尼克斯医药公司 | 用于hcv感染的2′-氯核苷类似物 |
| EP2909223B1 (en) | 2012-10-19 | 2017-03-22 | Idenix Pharmaceuticals LLC | Dinucleotide compounds for hcv infection |
| WO2014066239A1 (en) | 2012-10-22 | 2014-05-01 | Idenix Pharmaceuticals, Inc. | 2',4'-bridged nucleosides for hcv infection |
| EP2938624A1 (en) | 2012-11-14 | 2015-11-04 | IDENIX Pharmaceuticals, Inc. | D-alanine ester of sp-nucleoside analog |
| EP2920195A1 (en) | 2012-11-14 | 2015-09-23 | IDENIX Pharmaceuticals, Inc. | D-alanine ester of rp-nucleoside analog |
| WO2014099941A1 (en) | 2012-12-19 | 2014-06-26 | Idenix Pharmaceuticals, Inc. | 4'-fluoro nucleosides for the treatment of hcv |
| KR102532198B1 (ko) | 2012-12-21 | 2023-05-11 | 얀센 바이오파마, 인코퍼레이트. | 치환된 뉴클레오사이드, 뉴클레오타이드 및 그것의 유사체 |
| HUE047777T2 (hu) | 2013-01-31 | 2020-05-28 | Gilead Pharmasset Llc | Két vírusellenes vegyület kombinációs készítménye |
| US10034893B2 (en) | 2013-02-01 | 2018-07-31 | Enanta Pharmaceuticals, Inc. | 5, 6-D2 uridine nucleoside/tide derivatives |
| WO2014121417A1 (en) | 2013-02-07 | 2014-08-14 | Merck Sharp & Dohme Corp. | Tetracyclic heterocycle compounds and methods of use thereof for the treatment of hepatitis c |
| WO2014121418A1 (en) | 2013-02-07 | 2014-08-14 | Merck Sharp & Dohme Corp. | Tetracyclic heterocycle compounds and methods of use thereof for the treatment of hepatitis c |
| WO2014137930A1 (en) | 2013-03-04 | 2014-09-12 | Idenix Pharmaceuticals, Inc. | Thiophosphate nucleosides for the treatment of hcv |
| EP2970358B1 (en) | 2013-03-04 | 2021-06-30 | Idenix Pharmaceuticals LLC | 3'-deoxy nucleosides for the treatment of hcv |
| US20140271547A1 (en) | 2013-03-13 | 2014-09-18 | Idenix Pharmaceuticals, Inc. | Amino acid phosphoramidate pronucleotides of 2'-cyano, azido and amino nucleosides for the treatment of hcv |
| RU2534613C2 (ru) | 2013-03-22 | 2014-11-27 | Александр Васильевич Иващенко | Алкил 2-{ [(2r,3s,5r)-5-(4-амино-2-оксо-2н-пиримидин-1-ил)- -гидрокси-тетрагидро-фуран-2-илметокси]-фенокси-фосфориламино} -пропионаты, нуклеозидные ингибиторы рнк-полимеразы hcv ns5b, способы их получения и применения |
| WO2014165542A1 (en) | 2013-04-01 | 2014-10-09 | Idenix Pharmaceuticals, Inc. | 2',4'-fluoro nucleosides for the treatment of hcv |
| BR112015025716A2 (pt) | 2013-04-12 | 2017-07-18 | Achillion Pharmaceuticals Inc | pró-fármacos de nucleosídeo submetidos a deutério úteis para o tratamento de hcv |
| US10005779B2 (en) | 2013-06-05 | 2018-06-26 | Idenix Pharmaceuticals Llc | 1′,4′-thio nucleosides for the treatment of HCV |
| WO2015017713A1 (en) | 2013-08-01 | 2015-02-05 | Idenix Pharmaceuticals, Inc. | D-amino acid phosphoramidate pronucleotides of halogeno pyrimidine compounds for liver disease |
| EP4005560A1 (en) | 2013-08-27 | 2022-06-01 | Gilead Pharmasset LLC | Combination formulation of two antiviral compounds |
| PL3043803T3 (pl) | 2013-09-11 | 2022-11-07 | Emory University | Kompozycje nukleotydowe i nukleozydowe oraz ich zastosowanie |
| EP3046924A1 (en) | 2013-09-20 | 2016-07-27 | IDENIX Pharmaceuticals, Inc. | Hepatitis c virus inhibitors |
| WO2015061683A1 (en) | 2013-10-25 | 2015-04-30 | Idenix Pharmaceuticals, Inc. | D-amino acid phosphoramidate and d-alanine thiophosphoramidate pronucleotides of nucleoside compounds useful for the treatment of hcv |
| EP3063165A1 (en) | 2013-11-01 | 2016-09-07 | Idenix Pharmaceuticals LLC | D-alanine phosphoramidate pronucleotides of 2'-methyl 2'-fluoro guanosine nucleoside compounds for the treatment of hcv |
| EP3074399A1 (en) | 2013-11-27 | 2016-10-05 | Idenix Pharmaceuticals LLC | 2'-dichloro and 2'-fluoro-2'-chloro nucleoside analogues for hcv infection |
| WO2015095419A1 (en) | 2013-12-18 | 2015-06-25 | Idenix Pharmaceuticals, Inc. | 4'-or nucleosides for the treatment of hcv |
| EP3105238A4 (en) | 2014-02-13 | 2017-11-08 | Ligand Pharmaceuticals, Inc. | Prodrug compounds and their uses |
| EP3113763A1 (en) | 2014-03-05 | 2017-01-11 | Idenix Pharmaceuticals LLC | Solid prodrug forms of 2'-chloro-2'-methyl uridine for hcv |
| US20170135990A1 (en) | 2014-03-05 | 2017-05-18 | Idenix Pharmaceuticals Llc | Pharmaceutical compositions comprising a 5,5-fused heteroarylene flaviviridae inhibitor and their use for treating or preventing flaviviridae infection |
| WO2015134560A1 (en) | 2014-03-05 | 2015-09-11 | Idenix Pharmaceuticals, Inc. | Solid forms of a flaviviridae virus inhibitor compound and salts thereof |
| WO2015161137A1 (en) | 2014-04-16 | 2015-10-22 | Idenix Pharmaceuticals, Inc. | 3'-substituted methyl or alkynyl nucleosides for the treatment of hcv |
| JP2017520545A (ja) | 2014-07-02 | 2017-07-27 | リガンド・ファーマシューティカルズ・インコーポレイテッド | プロドラッグ化合物およびそれらの使用 |
| US9675632B2 (en) | 2014-08-26 | 2017-06-13 | Enanta Pharmaceuticals, Inc. | Nucleoside and nucleotide derivatives |
| TWI698444B (zh) | 2014-10-29 | 2020-07-11 | 美商基利科學股份有限公司 | 製備核糖苷的方法 |
| WO2016073756A1 (en) | 2014-11-06 | 2016-05-12 | Enanta Pharmaceuticals, Inc. | Deuterated nucleoside/tide derivatives |
| US9732110B2 (en) | 2014-12-05 | 2017-08-15 | Enanta Pharmaceuticals, Inc. | Nucleoside and nucleotide derivatives |
| HRP20211456T1 (hr) | 2014-12-26 | 2021-12-24 | Emory University | Protuvirusni derivati n4-hidroksicitidina |
| IL302877A (en) | 2015-03-06 | 2023-07-01 | Atea Pharmaceuticals Inc | Cell-D-2'-deoxy-2'-alpha-fluoro-2'-cell-C-modified-2-different-N6-purine modified nucleotides for the treatment of hepatitis C virus |
| JP6743135B2 (ja) * | 2015-09-02 | 2020-08-19 | アッヴィ・インコーポレイテッド | 抗ウィルス性テトラヒドロフラン誘導体 |
| ES2918585T3 (es) | 2015-09-16 | 2022-07-19 | Gilead Sciences Inc | Métodos para el tratamiento de infecciones por el virus Arenaviridae |
| EP3454856B1 (en) | 2016-05-10 | 2024-09-11 | C4 Therapeutics, Inc. | Heterocyclic degronimers for target protein degradation |
| CN109641874A (zh) | 2016-05-10 | 2019-04-16 | C4医药公司 | 用于靶蛋白降解的c3-碳连接的戊二酰亚胺降解决定子体 |
| WO2017197051A1 (en) | 2016-05-10 | 2017-11-16 | C4 Therapeutics, Inc. | Amine-linked c3-glutarimide degronimers for target protein degradation |
| ES2990061T3 (es) | 2016-05-10 | 2024-11-28 | C4 Therapeutics Inc | Degronímeros espirocíclicos para la degradación de proteínas diana |
| US10202412B2 (en) | 2016-07-08 | 2019-02-12 | Atea Pharmaceuticals, Inc. | β-D-2′-deoxy-2′-substituted-4′-substituted-2-substituted-N6-substituted-6-aminopurinenucleotides for the treatment of paramyxovirus and orthomyxovirus infections |
| LU100724B1 (en) | 2016-07-14 | 2018-07-31 | Atea Pharmaceuticals Inc | Beta-d-2'-deoxy-2'-alpha-fluoro-2'-beta-c-substituted-4'-fluoro-n6-substituted-6-amino-2-substituted purine nucleotides for the treatment of hepatitis c virus infection |
| MA45925A (fr) * | 2016-08-12 | 2019-06-19 | Janssen Biopharma Inc | Nucléosides et nucléotides substitués et leurs analogues |
| KR102456417B1 (ko) | 2016-09-07 | 2022-10-19 | 아테아 파마슈티컬즈, 인크. | Rna 바이러스 치료를 위한 2'-치환된-n6-치환된 퓨린 뉴클레오티드 |
| RS66554B1 (sr) | 2017-02-01 | 2025-03-31 | Atea Pharmaceuticals Inc | Nukleotid hemi-sulfat so za lečenje virusa hepatitisa c |
| CN110869028B (zh) | 2017-03-14 | 2023-01-20 | 吉利德科学公司 | 治疗猫冠状病毒感染的方法 |
| WO2018204198A1 (en) | 2017-05-01 | 2018-11-08 | Gilead Sciences, Inc. | Crystalline forms of (s) 2 ethylbutyl 2 (((s) (((2r,3s,4r,5r) 5 (4 aminopyrrolo[2,1-f] [1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2 yl)methoxy)(phenoxy) phosphoryl)amino)propanoate |
| EP3641762A4 (en) | 2017-06-20 | 2021-03-10 | C4 Therapeutics, Inc. | N / O-LINKED DEGRONES AND DEGRONIMERS FOR PROTEIN DEGRADATION |
| EP3645836B1 (en) | 2017-06-26 | 2025-02-26 | HRL Laboratories, LLC | System and method for generating output of a downhole inertial measurement unit |
| US10675296B2 (en) | 2017-07-11 | 2020-06-09 | Gilead Sciences, Inc. | Compositions comprising an RNA polymerase inhibitor and cyclodextrin for treating viral infections |
| SG11202004403QA (en) | 2017-12-07 | 2020-06-29 | Univ Emory | N4-hydroxycytidine and derivatives and anti-viral uses related thereto |
| JP2021509907A (ja) | 2018-01-09 | 2021-04-08 | リガンド・ファーマシューティカルズ・インコーポレイテッド | アセタール化合物およびその治療的使用 |
| EP3773753A4 (en) | 2018-04-10 | 2021-12-22 | ATEA Pharmaceuticals, Inc. | TREATMENT OF PATIENTS INFECTED WITH THE HEPATITIS C VIRUS WITH CIRRHOSIS |
| US11535645B2 (en) * | 2018-10-17 | 2022-12-27 | Xibin Liao | 6-mercaptopurine nucleoside analogues |
| CN112898292A (zh) | 2019-12-03 | 2021-06-04 | 微境生物医药科技(上海)有限公司 | 新型极光激酶抑制剂及其用途 |
| JP2023512656A (ja) | 2020-01-27 | 2023-03-28 | ギリアード サイエンシーズ, インコーポレイテッド | SARS CoV-2感染を治療するための方法 |
| US10874687B1 (en) | 2020-02-27 | 2020-12-29 | Atea Pharmaceuticals, Inc. | Highly active compounds against COVID-19 |
| WO2021183750A2 (en) | 2020-03-12 | 2021-09-16 | Gilead Sciences, Inc. | Methods of preparing 1'-cyano nucleosides |
| US11701372B2 (en) | 2020-04-06 | 2023-07-18 | Gilead Sciences, Inc. | Inhalation formulations of 1'-cyano substituted carba-nucleoside analogs |
| AU2021281351A1 (en) | 2020-05-29 | 2023-01-19 | Gilead Sciences, Inc. | Remdesivir treatment methods |
| PH12022553530A1 (en) | 2020-06-24 | 2024-06-24 | Gilead Sciences Inc | 1'-cyano nucleoside analogs and uses thereof |
| CN116568688B (zh) | 2020-08-27 | 2025-11-21 | 吉利德科学公司 | 用于治疗病毒感染的化合物和方法 |
| WO2022115615A1 (en) * | 2020-11-25 | 2022-06-02 | Northeastern University | Cyclic peptides with antimicrobial properties |
| US20250114389A1 (en) * | 2021-04-09 | 2025-04-10 | Emory University | Nucleosides and nucleotides analogs as antiviral agents |
| CA3174073A1 (en) | 2021-06-17 | 2022-12-17 | Atea Pharmaceuticals, Inc. | Advantageous anti-hcv combination therapy |
| JP2025508942A (ja) | 2022-03-02 | 2025-04-10 | ギリアード サイエンシーズ, インコーポレイテッド | ウイルス感染症の治療のための化合物及び方法 |
| US12357577B1 (en) | 2024-02-02 | 2025-07-15 | Gilead Sciences, Inc. | Pharmaceutical formulations and uses thereof |
Family Cites Families (340)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US87873A (en) * | 1869-03-16 | Perry prettyman | ||
| US83307A (en) * | 1868-10-20 | Improvement in wash-boilehs | ||
| US8841A (en) * | 1852-03-30 | Sice-httxieb | ||
| US28013A (en) * | 1860-04-24 | Improved bullet-ladle | ||
| US6458772B1 (en) | 1909-10-07 | 2002-10-01 | Medivir Ab | Prodrugs |
| US3074929A (en) | 1955-08-11 | 1963-01-22 | Burroughs Wellcome Co | Glycosides of 6-mercaptopurine |
| GB924246A (en) | 1958-12-23 | 1963-04-24 | Wellcome Found | Purine derivatives and their preparation |
| US3116282A (en) | 1960-04-27 | 1963-12-31 | Upjohn Co | Pyrimidine nucleosides and process |
| GB984877A (en) | 1962-08-16 | 1965-03-03 | Waldhof Zellstoff Fab | Improvements in and relating to 6-halonucleosides |
| FR1498856A (enExample) | 1965-11-15 | 1968-01-10 | ||
| GB1163103A (en) * | 1965-11-15 | 1969-09-04 | Merck & Co Inc | Ribofuranosyl Purine Derivatives |
| FR1521076A (fr) * | 1966-05-02 | 1968-04-12 | Merck & Co Inc | Nucléosides de purines substituées |
| DE1695411A1 (de) | 1966-05-02 | 1971-04-15 | Merck & Co Inc | Substituierte Purin-Nucleoside und Verfahren zu deren Herstellung |
| US3480613A (en) | 1967-07-03 | 1969-11-25 | Merck & Co Inc | 2-c or 3-c-alkylribofuranosyl - 1-substituted compounds and the nucleosides thereof |
| DE2122991C2 (de) | 1971-05-04 | 1982-06-09 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Verfahren zur Herstellung von Cytosin- und 6-Azacytosinnucleosiden |
| USRE29835E (en) | 1971-06-01 | 1978-11-14 | Icn Pharmaceuticals | 1,2,4-Triazole nucleosides |
| US3798209A (en) | 1971-06-01 | 1974-03-19 | Icn Pharmaceuticals | 1,2,4-triazole nucleosides |
| JPS4848495A (enExample) | 1971-09-21 | 1973-07-09 | ||
| US4022889A (en) | 1974-05-20 | 1977-05-10 | The Upjohn Company | Therapeutic compositions of antibiotic U-44,590 and methods for using the same |
| DE2508312A1 (de) | 1975-02-24 | 1976-09-02 | Schering Ag | Neues verfahren zur herstellung von nucleosiden |
| US4058602A (en) | 1976-08-09 | 1977-11-15 | The United States Of America As Represented By The Department Of Health, Education And Welfare | Synthesis, structure, and antitumor activity of 5,6-dihydro-5-azacytidine |
| DE2757365A1 (de) | 1977-12-20 | 1979-06-21 | Schering Ag | Neues verfahren zur herstellung von nucleosiden |
| DD140254A1 (de) | 1978-12-04 | 1980-02-20 | Dieter Baerwolff | Verfahren zur herstellung von 4-substituierten pyrimidin-nucleosiden |
| DE2852721A1 (de) | 1978-12-06 | 1980-06-26 | Basf Ag | Verfahren zur reindarstellung von kaliumribonat und ribonolacton |
| US4239753A (en) | 1978-12-12 | 1980-12-16 | The Upjohn Company | Composition of matter and process |
| US4522811A (en) | 1982-07-08 | 1985-06-11 | Syntex (U.S.A.) Inc. | Serial injection of muramyldipeptides and liposomes enhances the anti-infective activity of muramyldipeptides |
| FR2562543B1 (fr) | 1984-04-10 | 1987-09-25 | Elf Aquitaine | Nouveaux phosphonites cycliques, leur preparation et applications |
| NL8403224A (nl) | 1984-10-24 | 1986-05-16 | Oce Andeno Bv | Dioxafosforinanen, de bereiding ervan en de toepassing voor het splitsen van optisch actieve verbindingen. |
| KR880000094B1 (ko) | 1984-12-07 | 1988-02-23 | 보령제약 주식회사 | 뉴클레오시드 유도체의 제조방법 |
| JPS61204193A (ja) | 1985-03-05 | 1986-09-10 | Takeda Chem Ind Ltd | シトシンヌクレオシド類の製造法 |
| US5223263A (en) | 1988-07-07 | 1993-06-29 | Vical, Inc. | Liponucleotide-containing liposomes |
| US6448392B1 (en) | 1985-03-06 | 2002-09-10 | Chimerix, Inc. | Lipid derivatives of antiviral nucleosides: liposomal incorporation and method of use |
| JPS61212592A (ja) | 1985-03-19 | 1986-09-20 | Tokyo Tanabe Co Ltd | D−リボ−スの製造方法 |
| US4605659A (en) | 1985-04-30 | 1986-08-12 | Syntex (U.S.A.) Inc. | Purinyl or pyrimidinyl substituted hydroxycyclopentane compounds useful as antivirals |
| JPS61263995A (ja) | 1985-05-16 | 1986-11-21 | Takeda Chem Ind Ltd | シトシンヌクレオシド類の製造法 |
| US4754026A (en) | 1985-06-04 | 1988-06-28 | Takeda Chemical Industries, Ltd. | Conversion of uracil derivatives to cytosine derivatives |
| US5455339A (en) | 1986-05-01 | 1995-10-03 | University Of Georgia Research Foundation, Inc. | Method for the preparation of 2',3'-dideoxy and 2',3'-dideoxydide-hydro nucleosides |
| JPH0699467B2 (ja) | 1987-03-04 | 1994-12-07 | ヤマサ醤油株式会社 | 2▲’▼−デオキシ−2▲’▼(s)−アルキルピリミジンヌクレオシド誘導体 |
| JPS63215894A (ja) | 1987-03-04 | 1988-09-08 | Hitachi Ltd | 増圧装置付電動ポンプ |
| DE3714473A1 (de) | 1987-04-30 | 1988-11-10 | Basf Ag | Kontinuierliches verfahren zur epimerisierung von zuckern, insbesondere von d-arabinose zu d-ribose |
| GB8719367D0 (en) | 1987-08-15 | 1987-09-23 | Wellcome Found | Therapeutic compounds |
| US5246924A (en) | 1987-09-03 | 1993-09-21 | Sloan-Kettering Institute For Cancer Research | Method for treating hepatitis B virus infections using 1-(2'-deoxy-2'-fluoro-beta-D-arabinofuranosyl)-5-ethyluracil |
| WO1989002733A1 (en) | 1987-09-22 | 1989-04-06 | The Regents Of The University Of California | Liposomal nucleoside analogues for treating aids |
| US4880784A (en) | 1987-12-21 | 1989-11-14 | Brigham Young University | Antiviral methods utilizing ribofuranosylthiazolo[4,5-d]pyrimdine derivatives |
| US4996308A (en) * | 1988-03-25 | 1991-02-26 | Merrell Dow Pharmaceuticals Inc. | Derivatives with unsaturated substitutions for the 5'-hydroxymethyl group |
| NZ229453A (en) | 1988-06-10 | 1991-08-27 | Univ Minnesota & Southern Rese | A pharmaceutical composition containing purine derivatives with nucleosides such as azt, as antiviral agents |
| US5122517A (en) | 1988-06-10 | 1992-06-16 | Regents Of The University Of Minnesota | Antiviral combination comprising nucleoside analogs |
| GB8815265D0 (en) | 1988-06-27 | 1988-08-03 | Wellcome Found | Therapeutic nucleosides |
| US6599887B2 (en) | 1988-07-07 | 2003-07-29 | Chimerix, Inc. | Methods of treating viral infections using antiviral liponucleotides |
| US6252060B1 (en) | 1988-07-07 | 2001-06-26 | Nexstar Pharmaceuticals, Inc. | Antiviral liponucleosides: treatment of hepatitis B |
| SE8802687D0 (sv) | 1988-07-20 | 1988-07-20 | Astra Ab | Nucleoside derivatives |
| US5744600A (en) | 1988-11-14 | 1998-04-28 | Institute Of Organic Chemistry And Biochemistry Of The Academy Of Sciences Of The Czech Republic | Phosphonomethoxy carbocyclic nucleosides and nucleotides |
| US5616702A (en) * | 1988-11-15 | 1997-04-01 | Merrell Pharmaceuticals Inc. | 2-'-ethenylidene cytidine, uridine and guanosine derivatives |
| US5705363A (en) | 1989-03-02 | 1998-01-06 | The Women's Research Institute | Recombinant production of human interferon τ polypeptides and nucleic acids |
| US5411947A (en) | 1989-06-28 | 1995-05-02 | Vestar, Inc. | Method of converting a drug to an orally available form by covalently bonding a lipid to the drug |
| US5194654A (en) | 1989-11-22 | 1993-03-16 | Vical, Inc. | Lipid derivatives of phosphonoacids for liposomal incorporation and method of use |
| US5118672A (en) | 1989-07-10 | 1992-06-02 | University Of Georgia Research Foundation | 5'-diphosphohexose nucleoside pharmaceutical compositions |
| US5463092A (en) | 1989-11-22 | 1995-10-31 | Vestar, Inc. | Lipid derivatives of phosphonacids for liposomal incorporation and method of use |
| US5026687A (en) | 1990-01-03 | 1991-06-25 | The United States Of America As Represented By The Department Of Health And Human Services | Treatment of human retroviral infections with 2',3'-dideoxyinosine alone and in combination with other antiviral compounds |
| US6060592A (en) | 1990-01-11 | 2000-05-09 | Isis Pharmaceuticals, Inc. | Pyrimidine nucleoside compounds and oligonucleoside compounds containing same |
| US5200514A (en) | 1990-01-19 | 1993-04-06 | University Of Georgia Research Foundation, Inc. | Synthesis of 2'-deoxypyrimidine nucleosides |
| US5204466A (en) | 1990-02-01 | 1993-04-20 | Emory University | Method and compositions for the synthesis of bch-189 and related compounds |
| WO1991016920A1 (en) | 1990-05-07 | 1991-11-14 | Vical, Inc. | Lipid prodrugs of salicylate and nonsteroidal anti-inflammatory drugs |
| FR2662165B1 (fr) | 1990-05-18 | 1992-09-11 | Univ Paris Curie | Derives nucleosidiques branches, leur procede de preparation et leur utilisation a titre de medicament. |
| EP0531452A4 (en) | 1990-05-29 | 1993-06-09 | Vical, Inc. | Synthesis of glycerol di- and triphosphate derivatives |
| CA2083961A1 (en) | 1990-05-29 | 1991-11-30 | Henk Van Den Bosch | Synthesis of glycerol di- and triphosphate derivatives |
| DE69115694T2 (de) | 1990-06-13 | 1996-10-17 | Arnold Newton Mass. Glazier | Phosphorylierte prodrugs |
| US5627165A (en) | 1990-06-13 | 1997-05-06 | Drug Innovation & Design, Inc. | Phosphorous prodrugs and therapeutic delivery systems using same |
| JP2559917B2 (ja) * | 1990-06-15 | 1996-12-04 | 三共株式会社 | ピリミジンヌクレオシド誘導体 |
| US5372808A (en) | 1990-10-17 | 1994-12-13 | Amgen Inc. | Methods and compositions for the treatment of diseases with consensus interferon while reducing side effect |
| US5149794A (en) | 1990-11-01 | 1992-09-22 | State Of Oregon | Covalent lipid-drug conjugates for drug targeting |
| US5543390A (en) | 1990-11-01 | 1996-08-06 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University | Covalent microparticle-drug conjugates for biological targeting |
| US5256641A (en) | 1990-11-01 | 1993-10-26 | State Of Oregon | Covalent polar lipid-peptide conjugates for immunological targeting |
| US5543389A (en) | 1990-11-01 | 1996-08-06 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education On Behalf Of The Oregon Health Sciences University, A Non Profit Organization | Covalent polar lipid-peptide conjugates for use in salves |
| US5827819A (en) | 1990-11-01 | 1998-10-27 | Oregon Health Sciences University | Covalent polar lipid conjugates with neurologically active compounds for targeting |
| IL100502A (en) | 1991-01-03 | 1995-12-08 | Iaf Biochem Int | PHARMACEUTICAL PREPARATIONS CONTAINING CIS-4-AMINO-1-) 2-HYDROXIMETHIL-1,3-OXETYOLEN-5-IL (- |
| JPH04266880A (ja) | 1991-02-22 | 1992-09-22 | Japan Tobacco Inc | 3 −dpa− ラクトンの製造方法 |
| CA2105486C (en) | 1991-03-06 | 2003-10-28 | George Robert Painter Iii | Therapeutic nucleosides |
| WO1992018517A1 (en) | 1991-04-17 | 1992-10-29 | Yale University | Method of treating or preventing hepatitis b virus |
| US5157027A (en) | 1991-05-13 | 1992-10-20 | E. R. Squibb & Sons, Inc. | Bisphosphonate squalene synthetase inhibitors and method |
| JPH07500573A (ja) | 1991-07-12 | 1995-01-19 | ネクススター・ファーマシューティカルズ・インコーポレイテッド | 抗ウィルス性リポヌクレオシド:b型肝炎の治療 |
| JPH0525152A (ja) | 1991-07-22 | 1993-02-02 | Japan Tobacco Inc | 3−dpa−ラクトンの製造法 |
| US5554728A (en) | 1991-07-23 | 1996-09-10 | Nexstar Pharmaceuticals, Inc. | Lipid conjugates of therapeutic peptides and protease inhibitors |
| TW224053B (enExample) | 1991-09-13 | 1994-05-21 | Paul B Chretien | |
| US5676942A (en) | 1992-02-10 | 1997-10-14 | Interferon Sciences, Inc. | Composition containing human alpha interferon species proteins and method for use thereof |
| DE4207363A1 (de) | 1992-03-04 | 1993-09-09 | Max Delbrueck Centrum | Antivirale nucleosidanaloga, ihre herstellung und ihre pharmazeutische verwendung |
| US5821357A (en) | 1992-06-22 | 1998-10-13 | Eli Lilly And Company | Stereoselective glycosylation process for preparing 2'-deoxy-2',2'-difluoropurine and triazole nucleosides |
| US5256797A (en) | 1992-06-22 | 1993-10-26 | Eli Lilly And Company | Process for separating 2-deoxy-2,2-difluoro-D-ribofuranosyl alkylsulfonate anomers |
| US5401861A (en) | 1992-06-22 | 1995-03-28 | Eli Lilly And Company | Low temperature process for preparing alpha-anomer enriched 2-deoxy-2,2-difluoro-D-ribofuranosyl sulfonates |
| US5606048A (en) | 1992-06-22 | 1997-02-25 | Eli Lilly And Company | Stereoselective glycosylation process for preparing 2'-Deoxy-2', 2'-difluoronucleosides and 2'-deoxy-2'-fluoronucleosides |
| US5371210A (en) | 1992-06-22 | 1994-12-06 | Eli Lilly And Company | Stereoselective fusion glycosylation process for preparing 2'-deoxy-2',2'-difluoronucleosides and 2'-deoxy-2'-fluoronucleosides |
| WO1994001117A1 (en) | 1992-07-02 | 1994-01-20 | The Wellcome Foundation Limited | Therapeutic nucleosides |
| DE4224737A1 (de) | 1992-07-27 | 1994-02-03 | Herbert Prof Dr Schott | Neue Cytosinnucleosidanaloga, Verfahren zu ihrer Herstellung und ihre Verwendung |
| US5256924A (en) * | 1992-08-10 | 1993-10-26 | Allied-Signal Inc. | Superconducting commutator for DC machines |
| KR100252451B1 (ko) | 1992-09-01 | 2000-04-15 | 피터 지. 스트링거 | 뉴클레오사이드의아노머화방법 |
| US6423489B1 (en) | 1992-09-10 | 2002-07-23 | Isis Pharmaceuticals, Inc. | Compositions and methods for treatment of Hepatitis C virus-associated diseases |
| US6391542B1 (en) | 1992-09-10 | 2002-05-21 | Isis Pharmaceuticals, Inc. | Compositions and methods for treatment of Hepatitis C virus-associated diseases |
| DK0662157T3 (da) | 1992-09-10 | 2001-08-27 | Isis Pharmaceuticals Inc | Præparater og fremgangsmåde til behandling af Hepatitis C-virus-associerede sygdomme |
| US6433159B1 (en) | 1992-09-10 | 2002-08-13 | Isis Pharmaceuticals, Inc. | Compositions and methods for treatment of Hepatitis C virus associated diseases |
| US6174868B1 (en) | 1992-09-10 | 2001-01-16 | Isis Pharmaceuticals, Inc. | Compositions and methods for treatment of hepatitis C virus-associated diseases |
| JPH06135988A (ja) | 1992-10-22 | 1994-05-17 | Toagosei Chem Ind Co Ltd | ヌクレオシド誘導体 |
| GB9226729D0 (en) | 1992-12-22 | 1993-02-17 | Wellcome Found | Therapeutic combination |
| JPH06211890A (ja) | 1993-01-12 | 1994-08-02 | Yamasa Shoyu Co Ltd | 2’−デオキシ−2’(s)−置換アルキルシチジン誘導体 |
| JPH06228186A (ja) | 1993-01-29 | 1994-08-16 | Yamasa Shoyu Co Ltd | 2’−デオキシ−(2’s)−アルキルピリミジンヌクレオシド誘導体 |
| US5496546A (en) | 1993-02-24 | 1996-03-05 | Jui H. Wang | Compositions and methods of application of reactive antiviral polyadenylic acid derivatives |
| GB9307043D0 (en) | 1993-04-05 | 1993-05-26 | Norsk Hydro As | Chemical compounds |
| JP3312951B2 (ja) | 1993-04-08 | 2002-08-12 | 三菱化学株式会社 | オレフィン系熱可塑性樹脂組成物 |
| JPH08510236A (ja) | 1993-05-12 | 1996-10-29 | カール ワイ. ホステトラー | 局所使用のためのアシクロビル誘導体 |
| US5846964A (en) | 1993-07-19 | 1998-12-08 | Tokyo Tanabe Company Limited | Hepatitis C virus proliferation inhibitor |
| US6156501A (en) | 1993-10-26 | 2000-12-05 | Affymetrix, Inc. | Arrays of modified nucleic acid probes and methods of use |
| US5587362A (en) | 1994-01-28 | 1996-12-24 | Univ. Of Ga Research Foundation | L-nucleosides |
| US5908821A (en) | 1994-05-11 | 1999-06-01 | Procter & Gamble Company | Dye transfer inhibiting compositions with specifically selected metallo catalysts |
| WO1996001115A1 (en) | 1994-07-01 | 1996-01-18 | Pro-Neuron, Inc. | Pyrimidine nucleotide precursors for treatment of systemic inflammation and inflammatory hepatitis |
| DE4432623A1 (de) | 1994-09-14 | 1996-03-21 | Huels Chemische Werke Ag | Verfahren zur Bleichung von wäßrigen Tensidlösungen |
| US5696277A (en) | 1994-11-15 | 1997-12-09 | Karl Y. Hostetler | Antiviral prodrugs |
| PT747389E (pt) | 1994-12-13 | 2003-12-31 | Taiho Pharmaceutical Co Ltd | Derivados de nucleosido 3'-substituidos |
| GB9505025D0 (en) | 1995-03-13 | 1995-05-03 | Medical Res Council | Chemical compounds |
| JP3786447B2 (ja) | 1995-03-31 | 2006-06-14 | エーザイ株式会社 | C型肝炎の予防・治療剤 |
| DE19513330A1 (de) | 1995-04-03 | 1996-10-10 | Schering Ag | Neues Verfahren zur Herstellung von Nucleosiden |
| US5977061A (en) * | 1995-04-21 | 1999-11-02 | Institute Of Organic Chemistry And Biochemistry Of The Academy Of Sciences Of The Czech Republic | N6 - substituted nucleotide analagues and their use |
| JPH0959292A (ja) | 1995-08-25 | 1997-03-04 | Yamasa Shoyu Co Ltd | 4−アミノピリミジンヌクレオシドの製造法 |
| CA2231442A1 (en) | 1995-09-07 | 1997-03-13 | University Of Georgia Research Foundation, Inc. | Therapeutic azide compounds |
| EP0859833B1 (en) | 1995-09-27 | 2006-03-01 | Emory University | Recombinant hepatitis c virus rna replicase |
| US5908621A (en) | 1995-11-02 | 1999-06-01 | Schering Corporation | Polyethylene glycol modified interferon therapy |
| US5980884A (en) | 1996-02-05 | 1999-11-09 | Amgen, Inc. | Methods for retreatment of patients afflicted with Hepatitis C using consensus interferon |
| US5830905A (en) | 1996-03-29 | 1998-11-03 | Viropharma Incorporated | Compounds, compositions and methods for treatment of hepatitis C |
| US5633388A (en) | 1996-03-29 | 1997-05-27 | Viropharma Incorporated | Compounds, compositions and methods for treatment of hepatitis C |
| GB9609932D0 (en) | 1996-05-13 | 1996-07-17 | Hoffmann La Roche | Use of IL-12 and IFN alpha for the treatment of infectious diseases |
| US5891874A (en) | 1996-06-05 | 1999-04-06 | Eli Lilly And Company | Anti-viral compound |
| JP3927630B2 (ja) | 1996-09-27 | 2007-06-13 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | ウイルス感染症の予防・治療剤 |
| US5922757A (en) | 1996-09-30 | 1999-07-13 | The Regents Of The University Of California | Treatment and prevention of hepatic disorders |
| CZ120699A3 (cs) * | 1996-10-16 | 1999-09-15 | Icn Pharmaceuticals, Inc. | Monocyklická L-nukleosidová analoga a jejich využití |
| CA2266889A1 (en) * | 1996-10-16 | 1998-04-23 | Guangyi Wang | Purine l-nucleosides, analogs and uses thereof |
| CA2268391A1 (en) | 1996-10-18 | 1998-04-30 | Vertex Pharmaceuticals Incorporated | Inhibitors of serine proteases, particularly hepatitis c virus ns3 protease |
| EP0948256A4 (en) * | 1996-10-28 | 2007-10-24 | Univ Washington | INDUCTION OF VIRAL MUTATIONS BY INTRODUCTION TO ERROR-CODED RIBONUCLEOSIDE ANALOGUES IN VIRAL RNA |
| GB9623908D0 (en) | 1996-11-18 | 1997-01-08 | Hoffmann La Roche | Amino acid derivatives |
| US6248878B1 (en) | 1996-12-24 | 2001-06-19 | Ribozyme Pharmaceuticals, Inc. | Nucleoside analogs |
| HUP0001526A3 (en) | 1997-01-17 | 2002-10-28 | Icn Pharmaceuticals Inc Costa | Use of nucleozides for producing pharmaceutical compositions for cytokine related treatments of disease and the pharmaceutical compositions |
| CN1196701C (zh) | 1997-03-19 | 2005-04-13 | 埃莫里大学 | 1,3-氧硒戊环核苷的合成及抗人类免疫缺陷病毒和抗乙肝病毒活性 |
| ATE240936T1 (de) | 1997-06-30 | 2003-06-15 | Merz & Co Gmbh & Co | 1-amino-alkylcyclohexane als nmda-rezeptor- antagonisten |
| IL134233A0 (en) | 1997-08-11 | 2001-04-30 | Boehringer Ingelheim Ca Ltd | Hepatitis c inhibitor peptide analogues |
| DE69801970T2 (de) | 1997-09-21 | 2002-06-13 | Schering Corp., Kenilworth | Kombinationstherapie zur Entfernung von nachweisbarer HCV-RNS in Patienten mit chronischer Hepatitis C-Infektion |
| US6172046B1 (en) | 1997-09-21 | 2001-01-09 | Schering Corporation | Combination therapy for eradicating detectable HCV-RNA in patients having chronic Hepatitis C infection |
| US6472373B1 (en) | 1997-09-21 | 2002-10-29 | Schering Corporation | Combination therapy for eradicating detectable HCV-RNA in antiviral treatment naive patients having chronic hepatitis C infection |
| WO1999023104A2 (en) | 1997-10-30 | 1999-05-14 | The Government Of The United States Of America, Represented By The Secretary Of Health And Human Services | Antitumour uridine analogues |
| WO1999040916A1 (en) | 1998-02-12 | 1999-08-19 | G.D. Searle & Co. | Use of n-substituted-1,5-dideoxy-1,5-imino-d-glucitol compounds for treating hepatitis virus infections |
| WO1999043690A1 (en) | 1998-02-25 | 1999-09-02 | Rational Drug Design Laboratories | L-4'-arabinofuranonucleoside compound and medicine composition comprising the same |
| ATE344271T1 (de) | 1998-02-25 | 2006-11-15 | Univ Emory | 2'-fluoronukleoside |
| AU767599B2 (en) | 1998-03-06 | 2003-11-20 | Metabasis Therapeutics, Inc. | Novel prodrugs for phosphorus-containing compounds |
| KR100389853B1 (ko) | 1998-03-06 | 2003-08-19 | 삼성전자주식회사 | 카타로그정보의기록및재생방법 |
| US6312662B1 (en) | 1998-03-06 | 2001-11-06 | Metabasis Therapeutics, Inc. | Prodrugs phosphorus-containing compounds |
| GB9806815D0 (en) | 1998-03-30 | 1998-05-27 | Hoffmann La Roche | Amino acid derivatives |
| TW466112B (en) | 1998-04-14 | 2001-12-01 | Lilly Co Eli | Novel use of 2'-deoxy-2',2'-difluorocytidine for immunosuppressive therapy and pharmaceutical composition comprising the same |
| HU230432B1 (hu) | 1998-05-15 | 2016-06-28 | Merck Sharp & Dohme Corp | Ribavirint és alfa-interferont tartalmazó kombinált terápia vírusellenes kezelésben nem részesült, krónikus hepatitis C fertőzött paciensek kezelésében |
| US6833361B2 (en) | 1998-05-26 | 2004-12-21 | Ribapharm, Inc. | Nucleosides having bicyclic sugar moiety |
| HU228218B1 (en) | 1998-06-08 | 2013-02-28 | Hoffmann La Roche | Use of peg-ifn-alpha and ribavirin for the treatment of chronic hepatitis c |
| JP4294870B2 (ja) | 1998-08-10 | 2009-07-15 | インデニックス ファーマシューティカルズ リミティド | B型肝炎の治療のためのβ−L−2’−デオキシ−ヌクレオシド |
| US6444652B1 (en) | 1998-08-10 | 2002-09-03 | Novirio Pharmaceuticals Limited | β-L-2'-deoxy-nucleosides for the treatment of hepatitis B |
| US6277830B1 (en) | 1998-10-16 | 2001-08-21 | Schering Corporation | 5′-amino acid esters of ribavirin and the use of same to treat hepatitis C with interferon |
| CA2252144A1 (en) | 1998-10-16 | 2000-04-16 | University Of Alberta | Dual action anticancer prodrugs |
| IL142983A0 (en) | 1998-11-05 | 2002-04-21 | Centre Nat Rech Scient | Nucleosides with anti-hepatisis b virus activity |
| CA2348948C (en) | 1998-11-05 | 2007-09-18 | Gilles Gosselin | .beta.-l-2'-deoxy-nucleosides for the treatment of hiv infection |
| JP2003507322A (ja) | 1998-12-18 | 2003-02-25 | シェリング・コーポレーション | リバビリン−PEG化インターフェロン−α誘発HCV併用治療 |
| EP1175425A2 (en) | 1999-01-21 | 2002-01-30 | The Board Of Regents, The University Of Texas System | Inhibitors of intestinal apical membrane na/phosphate co-transportation |
| US6515028B1 (en) | 1999-02-12 | 2003-02-04 | G.D. Searle & Co. | Glucamine compounds for treating hepatitis virus infections |
| DE60002986T2 (de) | 1999-02-12 | 2004-05-19 | Glaxo Group Ltd., Greenford | Phosphoramidat-, mono-, di-, und triphosphatester von (1r, cis)-4-(6-amino-9h-purin-9-yl)-2-cyclopentene-1-methanol als antivirale mittel |
| JP2002537396A (ja) | 1999-02-22 | 2002-11-05 | バイオケム ファーマ インコーポレイテッド | 抗ウィルス活性を有する[1,8]ナフチリジン誘導体 |
| WO2000052015A2 (en) | 1999-03-05 | 2000-09-08 | Metabasis Therapeutics, Inc. | Novel phosphorus-containing prodrugs |
| US6831069B2 (en) | 1999-08-27 | 2004-12-14 | Ribapharm Inc. | Pyrrolo[2,3-d]pyrimidine nucleoside analogs |
| WO2001016671A1 (en) | 1999-09-01 | 2001-03-08 | Matsushita Electric Industrial Co., Ltd. | Digital data copyright protection system |
| JP4979866B2 (ja) | 1999-09-08 | 2012-07-18 | リガンド・ファーマシューティカルズ・インコーポレイテッド | 肝臓に特異的なドラッグデリバリーのためのプロドラッグ |
| US6566365B1 (en) | 1999-11-04 | 2003-05-20 | Biochem Pharma Inc. | Method for the treatment of Flaviviridea viral infection using nucleoside analogues |
| RU2273642C2 (ru) | 1999-12-22 | 2006-04-10 | Метабэйсис Терапьютикс, Инк. | Бисамидатные фосфонатные соединения, являющиеся ингибиторами фруктозо-1,6-бисфосфатазы |
| AU2338101A (en) | 1999-12-30 | 2001-07-16 | Biochem Pharma Inc. | Imidazopyrimidine nucleoside analogues with anti-hiv activity |
| WO2001060366A1 (en) | 2000-02-14 | 2001-08-23 | Pharmacia Corporation | Use of n-substituted-1,5-dideoxy-1,5-imino-d-glucitol compounds for treating hepatitis virus infections |
| US6495677B1 (en) | 2000-02-15 | 2002-12-17 | Kanda S. Ramasamy | Nucleoside compounds |
| US7056895B2 (en) | 2000-02-15 | 2006-06-06 | Valeant Pharmaceuticals International | Tirazole nucleoside analogs and methods for using same |
| US6455508B1 (en) | 2000-02-15 | 2002-09-24 | Kanda S. Ramasamy | Methods for treating diseases with tirazole and pyrrolo-pyrimidine ribofuranosyl nucleosides |
| JP2003523978A (ja) * | 2000-02-18 | 2003-08-12 | シャイアー・バイオケム・インコーポレイテッド | ヌクレオシドアナログを用いるflavivirus感染の処置もしくは予防するための方法 |
| FR2806095A1 (fr) | 2000-03-10 | 2001-09-14 | Gentech | Sequences polynucleotidiques purifiees de plantes et de levure codant pour des proteines qui interagissent avec les produits du genome des geminivirus |
| BR0110023A (pt) | 2000-04-13 | 2003-12-30 | Pharmasset Ltd | Derivados de nucleosìdeo 3'-ou-2' substituìdos para tratamento de infecções por vìrus da hepatite |
| AU2001255495A1 (en) | 2000-04-20 | 2001-11-07 | Schering Corporation | Ribavirin-interferon alfa combination therapy for eradicating detectable hcv-rnain patients having chronic hepatitis c infection |
| MY164523A (en) * | 2000-05-23 | 2017-12-29 | Univ Degli Studi Cagliari | Methods and compositions for treating hepatitis c virus |
| TR200402565T4 (tr) | 2000-05-26 | 2004-12-21 | Idenix (Cayman) Limited | Hepatit delta virüsü enfeksiyonunun tedavi edilmesinde ß-L-2'-deoksi-nükleosidlerin kullanımı |
| US6787526B1 (en) * | 2000-05-26 | 2004-09-07 | Idenix Pharmaceuticals, Inc. | Methods of treating hepatitis delta virus infection with β-L-2′-deoxy-nucleosides |
| IL153020A0 (en) * | 2000-05-26 | 2003-06-24 | Idenix Cayman Ltd | Methods and compositions for treating flaviviruses and pestiviruses |
| US6875751B2 (en) | 2000-06-15 | 2005-04-05 | Idenix Pharmaceuticals, Inc. | 3′-prodrugs of 2′-deoxy-β-L-nucleosides |
| MY141594A (en) | 2000-06-15 | 2010-05-14 | Novirio Pharmaceuticals Ltd | 3'-PRODRUGS OF 2'-DEOXY-ß-L-NUCLEOSIDES |
| US6815542B2 (en) | 2000-06-16 | 2004-11-09 | Ribapharm, Inc. | Nucleoside compounds and uses thereof |
| CA2409778A1 (en) | 2000-06-20 | 2001-12-27 | Incyte Genomics, Inc. | Secreted proteins |
| JP3629187B2 (ja) * | 2000-06-28 | 2005-03-16 | 株式会社東芝 | 電気フューズ、この電気フューズを備えた半導体装置及びその製造方法 |
| UA72612C2 (en) | 2000-07-06 | 2005-03-15 | Pyrido[2.3-d]pyrimidine and pyrimido[4.5-d]pyrimidine nucleoside analogues, prodrugs and method for inhibiting growth of neoplastic cells | |
| US6316174B1 (en) * | 2000-08-24 | 2001-11-13 | Eastman Kodak Company | Color negative film |
| US20030008841A1 (en) | 2000-08-30 | 2003-01-09 | Rene Devos | Anti-HCV nucleoside derivatives |
| SV2003000617A (es) | 2000-08-31 | 2003-01-13 | Lilly Co Eli | Inhibidores de la proteasa peptidomimetica ref. x-14912m |
| AU2001286959B2 (en) | 2000-09-01 | 2007-09-06 | Ribozyme Pharmaceuticals, Incorporated | Methods for synthesizing nucleosides, nucleoside derivatives and non-nucleoside derivatives |
| BR0114837A (pt) | 2000-10-18 | 2006-05-09 | Pharmasset Ltd | nucleosìdeos modificados para tratamento de infecções viróticas e proliferação celular anormal |
| BR0114636A (pt) | 2000-10-18 | 2004-02-10 | Schering Corp | Terapia combinada para hcv de interferon-alfa peguilado/ribavirina |
| AU2002228885A1 (en) | 2000-10-18 | 2002-04-29 | Pharmasset Inc | Simultaneous quantification of nucleic acids in diseased cells |
| WO2002048165A2 (en) | 2000-12-15 | 2002-06-20 | Pharmasset Ltd. | Antiviral agents for treatment of flaviviridae infections |
| DZ3487A1 (fr) | 2001-01-22 | 2002-07-25 | Merck Sharp & Dohme | Derives de nucleoside comme inhibiteurs de l'arn polymerase virale d'arn-dependant |
| US7105499B2 (en) | 2001-01-22 | 2006-09-12 | Merck & Co., Inc. | Nucleoside derivatives as inhibitors of RNA-dependent RNA viral polymerase |
| JP2004527504A (ja) | 2001-03-01 | 2004-09-09 | フアーマセツト・リミテツド | 2’,3’−ジデオキシ−2’,3’−ジデヒドロヌクレオシドの合成法 |
| GB0112617D0 (en) | 2001-05-23 | 2001-07-18 | Hoffmann La Roche | Antiviral nucleoside derivatives |
| GB0114286D0 (en) | 2001-06-12 | 2001-08-01 | Hoffmann La Roche | Nucleoside Derivatives |
| BR0210594A (pt) | 2001-06-22 | 2005-11-01 | Pharmasset Ltd | (beta)-d ou (beta)-l-3-halonucleosìdeo |
| WO2003024461A1 (en) | 2001-09-20 | 2003-03-27 | Schering Corporation | Hcv combination therapy |
| US20030070752A1 (en) | 2001-09-27 | 2003-04-17 | Kevin Bergevin | Method of manufacture for fluid handling barrier ribbon with polymeric tubes |
| EP1435974A4 (en) | 2001-09-28 | 2006-09-06 | Idenix Cayman Ltd | METHODS AND COMPOSITIONS FOR THE TREATMENT OF HEPATITIS C VIRUS USING 4 'MODIFIED NUCLEOSIDES |
| WO2003026675A1 (en) | 2001-09-28 | 2003-04-03 | Idenix (Cayman) Limited | Methods and compositions for treating flaviviruses and pestiviruses using 4'-modified nucleoside |
| AU2002351077A1 (en) | 2001-11-05 | 2003-05-19 | Exiqon A/S | Oligonucleotides modified with novel alpha-l-rna analogues |
| KR100978904B1 (ko) | 2001-12-14 | 2010-08-31 | 파마셋 인코포레이티드 | 바이러스 감염 치료용 n4-아실사이토신 뉴클레오사이드 |
| AU2002353165A1 (en) | 2001-12-17 | 2003-06-30 | Ribapharm Inc. | Deazapurine nucleoside libraries and compounds |
| US6965066B1 (en) | 2002-01-16 | 2005-11-15 | Actodyne General, Inc. | Elongated string support for a stringed musical instrument |
| WO2003062256A1 (en) | 2002-01-17 | 2003-07-31 | Ribapharm Inc. | 2'-beta-modified-6-substituted adenosine analogs and their use as antiviral agents |
| WO2003061385A1 (en) | 2002-01-17 | 2003-07-31 | Ribapharm Inc. | Tricyclic nucleoside library compounds, synthesis, and use as antiviral agents |
| AU2002341942A1 (en) | 2002-01-17 | 2003-09-02 | Ribapharm Inc. | Sugar modified nucleosides as viral replication inhibitors |
| AU2003209045B2 (en) | 2002-02-13 | 2006-12-14 | Isis Pharmaceuticals, Inc. | Methods of inhibiting orthopoxvirus replication with nucleoside compounds |
| JP2005522443A (ja) | 2002-02-14 | 2005-07-28 | フアーマセツト・リミテツド | 改変フッ素化ヌクレオシド類似体 |
| AU2003217863B9 (en) | 2002-02-28 | 2009-10-29 | Biota Scientific Management Pty Ltd | Nucleotide mimics and their prodrugs |
| AU2003214199A1 (en) | 2002-03-18 | 2003-10-08 | Massachusetts Institute Of Technology | Event-driven charge-coupled device design and applications therefor |
| US6968692B2 (en) * | 2002-04-26 | 2005-11-29 | Rolls-Royce Corporation | Fuel premixing module for gas turbine engine combustor |
| US7247621B2 (en) | 2002-04-30 | 2007-07-24 | Valeant Research & Development | Antiviral phosphonate compounds and methods therefor |
| RU2004135392A (ru) | 2002-05-06 | 2005-06-27 | Дженелэбс Текнолоджиз, Инк. (Us) | Производные нуклеозидов для лечения инфекции, вызываемой вирусом гепатита с |
| AU2003241621A1 (en) | 2002-05-24 | 2003-12-12 | Isis Pharmaceuticals, Inc. | Oligonucleotides having modified nucleoside units |
| WO2003099840A1 (en) | 2002-05-24 | 2003-12-04 | Isis Pharmaceuticals, Inc. | Oligonucleotides having modified nucleoside units |
| DE10226932A1 (de) | 2002-06-17 | 2003-12-24 | Bayer Ag | Strahlenhärtende Beschichtungsmittel |
| JP2005533777A (ja) | 2002-06-17 | 2005-11-10 | メルク エンド カムパニー インコーポレーテッド | Rna抗ウイルス剤としての炭素環ヌクレオシドアナログ |
| SE0201940D0 (sv) | 2002-06-20 | 2002-06-20 | Astrazeneca Ab | New combination II |
| US20070004669A1 (en) | 2002-06-21 | 2007-01-04 | Carroll Steven S | Nucleoside derivatives as inhibitors of rna-dependent rna viral polymerase |
| CA2488484A1 (en) | 2002-06-27 | 2004-01-08 | Merck & Co., Inc. | Nucleoside derivatives as inhibitors of rna-dependent rna viral polymerase |
| EP2799442A1 (en) | 2002-06-28 | 2014-11-05 | IDENIX Pharmaceuticals, Inc. | Modified 2' and 3' -nucleoside prodrugs for treating flaviridae infections |
| CN101172993A (zh) * | 2002-06-28 | 2008-05-07 | 埃迪尼克斯(开曼)有限公司 | 用于治疗黄病毒感染的2′-c-甲基-3′-o-l-缬氨酸酯核糖呋喃基胞苷 |
| MXPA04012779A (es) | 2002-06-28 | 2005-08-19 | Idenix Cayman Ltd | Profarmacos de 2'- y 3'-nucleosido para tratar infecciones por flaviviridae. |
| US7608600B2 (en) | 2002-06-28 | 2009-10-27 | Idenix Pharmaceuticals, Inc. | Modified 2′ and 3′-nucleoside prodrugs for treating Flaviviridae infections |
| KR20050035194A (ko) | 2002-06-28 | 2005-04-15 | 이데닉스 (케이만) 리미티드 | 플라비비리다에 감염 치료용 2'-c-메틸-3'-o-l-발린에스테르 리보푸라노실 사이티딘 |
| US20040003476A1 (en) * | 2002-07-08 | 2004-01-08 | Albert Bierria | Portable power driven scarifying tool for pipe ends |
| EP1556399A4 (en) | 2002-07-16 | 2007-09-26 | Merck & Co Inc | Nucleoside derivatives as inhibitors of RNA-dependent viral RNA polymerase |
| WO2004009020A2 (en) | 2002-07-24 | 2004-01-29 | Merck & Co., Inc. | Pyrrolopyrimidine thionucleoside analogs as antivirals |
| US20040067877A1 (en) | 2002-08-01 | 2004-04-08 | Schinazi Raymond F. | 2', 3'-Dideoxynucleoside analogues for the treatment or prevention of Flaviviridae infections |
| JP4085742B2 (ja) * | 2002-08-22 | 2008-05-14 | 株式会社ニコン | レンズ鏡筒及びこのレンズ鏡筒を備えたカメラシステム |
| AU2003261659A1 (en) | 2002-09-16 | 2004-04-30 | Kyeong Ho Kim | Decoration band |
| KR20050059199A (ko) | 2002-09-30 | 2005-06-17 | 제네랩스 테크놀로지스, 인코포레이티드 | C형 간염 바이러스 감염 치료용의 뉴클레오시드 유도체 |
| US7094768B2 (en) | 2002-09-30 | 2006-08-22 | Genelabs Technologies, Inc. | Nucleoside derivatives for treating hepatitis C virus infection |
| US20040229840A1 (en) | 2002-10-29 | 2004-11-18 | Balkrishen Bhat | Nucleoside derivatives as inhibitors of RNA-dependent RNA viral polymerase |
| EP1567169A4 (en) | 2002-11-04 | 2009-10-21 | Xenoport Inc | GEMCITABINE PROMOTERS, THEIR PHARMACEUTICAL COMPOSITIONS AND USES THEREOF |
| EP1563070A4 (en) | 2002-11-05 | 2008-05-28 | Isis Pharmaceuticals Inc | 2'-SUBSTITUTED OLIGOMER COMPOUNDS AND COMPOSITIONS FOR USE IN GENE MODULATIONS |
| AU2003291755A1 (en) | 2002-11-05 | 2004-06-07 | Isis Pharmaceuticals, Inc. | Oligomers comprising modified bases for binding cytosine and uracil or thymine and their use |
| ES2624353T3 (es) | 2002-11-15 | 2017-07-13 | Idenix Pharmaceuticals Llc | 2'-Metil nucleósidos en combinación con interferón y mutación de Flaviviridae |
| TWI332507B (en) | 2002-11-19 | 2010-11-01 | Hoffmann La Roche | Antiviral nucleoside derivatives |
| AU2003300901A1 (en) | 2002-12-12 | 2004-06-30 | Idenix (Cayman) Limited | Process for the production of 2'-branched nucleosides |
| RU2005123395A (ru) | 2002-12-23 | 2006-01-27 | Айденикс (Кайман) Лимитед (Ky) | Способ получения 3-нуклеозидных пролекарств |
| US7799908B2 (en) | 2003-01-15 | 2010-09-21 | Valeant Pharmaceuticals North America | Synthesis and use of 2′-substituted-N6 -modified nucleosides |
| AR043006A1 (es) | 2003-02-12 | 2005-07-13 | Merck & Co Inc | Proceso para preparar ribonucleosidos ramificados |
| AU2003225705A1 (en) | 2003-03-07 | 2004-09-30 | Ribapharm Inc. | Cytidine analogs and methods of use |
| CN101415719A (zh) | 2003-03-20 | 2009-04-22 | 微生物化学及药品有限公司 | 生产2’-脱氧-β-L-核苷的方法 |
| JP2006524227A (ja) | 2003-03-28 | 2006-10-26 | ファーマセット,インク. | フラビウイルス科ウイルス感染の治療のための化合物 |
| US7452901B2 (en) | 2003-04-25 | 2008-11-18 | Gilead Sciences, Inc. | Anti-cancer phosphonate analogs |
| CN1812995A (zh) | 2003-04-28 | 2006-08-02 | 艾登尼科斯(开曼)有限公司 | 工业化规模的核苷合成 |
| US20040259934A1 (en) | 2003-05-01 | 2004-12-23 | Olsen David B. | Inhibiting Coronaviridae viral replication and treating Coronaviridae viral infection with nucleoside compounds |
| EP1656093A2 (en) | 2003-05-14 | 2006-05-17 | Idenix (Cayman) Limited | Nucleosides for treatment of infection by corona viruses, toga viruses and picorna viruses |
| US20040229839A1 (en) | 2003-05-14 | 2004-11-18 | Biocryst Pharmaceuticals, Inc. | Substituted nucleosides, preparation thereof and use as inhibitors of RNA viral polymerases |
| WO2005020885A2 (en) | 2003-05-21 | 2005-03-10 | Isis Pharmaceuticals, Inc. | Compositions and methods for the treatment of severe acute respiratory syndrome (sars) |
| WO2004106356A1 (en) | 2003-05-27 | 2004-12-09 | Syddansk Universitet | Functionalized nucleotide derivatives |
| FI2604620T4 (fi) | 2003-05-30 | 2024-09-11 | Gilead Pharmasset Llc | Modifioituja fluorinoituja nukleosidianalogeja |
| KR20060026426A (ko) | 2003-06-19 | 2006-03-23 | 에프. 호프만-라 로슈 아게 | 4'-아지도 뉴클레오사이드 유도체의 제조 방법 |
| GB0317009D0 (en) | 2003-07-21 | 2003-08-27 | Univ Cardiff | Chemical compounds |
| CA2537140A1 (en) | 2003-08-29 | 2005-03-10 | The Nottingham Trent University | Gastric and prostate cancer associated antigens |
| JP2007522094A (ja) | 2003-09-22 | 2007-08-09 | アシドフィル エルエルシー | 小分子組成物、及びその組成物を使用して薬物効率を高めるための方法 |
| US7151089B2 (en) | 2003-10-27 | 2006-12-19 | Genelabs Technologies, Inc. | Nucleoside compounds for treating viral infections |
| US20050137141A1 (en) | 2003-10-24 | 2005-06-23 | John Hilfinger | Prodrug composition |
| WO2005054268A1 (en) | 2003-10-27 | 2005-06-16 | Genelabs Technologies, Inc. | Nucleoside compounds for treating viral infections |
| AU2004285923A1 (en) | 2003-10-27 | 2005-05-12 | Genelabs Technologies, Inc. | Nucleoside compounds for treating viral infections |
| US6908824B2 (en) * | 2003-11-06 | 2005-06-21 | Chartered Semiconductor Manufacturing Ltd. | Self-aligned lateral heterojunction bipolar transistor |
| JP2005302670A (ja) | 2004-04-16 | 2005-10-27 | Matsushita Electric Ind Co Ltd | 電子装置 |
| WO2006016930A2 (en) | 2004-05-14 | 2006-02-16 | Intermune, Inc. | Methods for treating hcv infection |
| JP5055564B2 (ja) | 2004-06-15 | 2012-10-24 | メルク・シャープ・エンド・ドーム・コーポレイション | Rna依存性rnaウイルスポリメラーゼの阻害剤としてのc−プリンヌクレオシド類似体 |
| WO2006002231A1 (en) | 2004-06-22 | 2006-01-05 | Biocryst Pharmaceuticals, Inc. | Aza nucleosides, preparation thereof and use as inhibitors of rna viral polymerases |
| EP1912643A2 (en) | 2004-06-23 | 2008-04-23 | Idenix (Cayman) Limited | 5-aza-7-deazapurine derivatives for treating infections with flaviviridae |
| CN1972696B (zh) | 2004-06-24 | 2010-08-11 | 默沙东公司 | 用于治疗rna依赖性rna病毒感染的核苷氨基磷酸芳基酯 |
| CN101023094B (zh) | 2004-07-21 | 2011-05-18 | 法莫赛特股份有限公司 | 烷基取代的2-脱氧-2-氟代-d-呋喃核糖基嘧啶和嘌呤及其衍生物的制备 |
| ES2386005T3 (es) | 2004-07-21 | 2012-08-07 | Gilead Pharmasset Llc | Preparación de 2-desoxi-2-fluoro-d-ribofuranosil pirimidinas y purinas sustituidas con alquilo y sus derivados |
| CA2577526A1 (en) | 2004-08-23 | 2006-03-02 | Joseph Armstrong Martin | Antiviral 4'-azido-nucleosides |
| WO2006037028A2 (en) | 2004-09-24 | 2006-04-06 | Idenix (Cayman) Limited | Methods and compositions for treating flaviviruses, pestiviruses and hepacivirus |
| EA200700718A1 (ru) | 2004-10-06 | 2007-12-28 | Мидженикс Инк. | Комбинированные противовирусные композиции, содержащие кастаноспермин, и способы их применения |
| CA2584367A1 (en) | 2004-10-21 | 2006-06-22 | Merck & Co., Inc. | Fluorinated pyrrolo[2,3-d]pyrimidine nucleosides for the treatment of rna-dependent rna viral infection |
| US7414031B2 (en) | 2004-11-22 | 2008-08-19 | Genelabs Technologies, Inc. | 5-nitro-nucleoside compounds for treating viral infections |
| EP1828217A2 (en) | 2004-12-16 | 2007-09-05 | Febit Biotech GmbH | Polymerase-independent analysis of the sequence of polynucleotides |
| EA200701669A1 (ru) | 2005-02-09 | 2008-02-28 | Мидженикс Инк. | Композиции и способы лечения или предотвращения инфекций, вызванных вирусами семейства flaviviridae |
| JP2008535932A (ja) | 2005-03-09 | 2008-09-04 | イデニクス(ケイマン)リミテツド | 抗ウィルス剤としての非天然塩基を有するヌクレオシド |
| DE102005012681A1 (de) | 2005-03-18 | 2006-09-21 | Weber, Lutz, Dr. | Neue 1,5-Dihydro-pyrrol-2-one |
| US8163744B2 (en) | 2005-03-18 | 2012-04-24 | Nexuspharma, Inc. | Tetrahydro-isoquinolin-1-ones for the treatment of cancer |
| GT200600119A (es) | 2005-03-24 | 2006-10-25 | Composiciones farmaceuticas | |
| WO2006116557A1 (en) | 2005-04-25 | 2006-11-02 | Genelabs Technologies, Inc. | Nucleoside compounds for treating viral infections |
| WO2006121820A1 (en) | 2005-05-05 | 2006-11-16 | Valeant Research & Development | Phosphoramidate prodrugs for treatment of viral infection |
| SMAP200700061A (it) | 2005-05-31 | 2007-12-28 | Novartis Ag | Trattamento delle malattie epatiche in cui il ferro svolge un ruolo nella patogenesi |
| CA2615626A1 (en) | 2005-07-18 | 2007-01-25 | Novartis Ag | Small animal model for hcv replication |
| JP2009504677A (ja) | 2005-08-12 | 2009-02-05 | メルク・エンド・カムパニー・インコーポレーテツド | 新規2’−c−メチル及び4’−c−メチルヌクレオシド誘導体 |
| AR057096A1 (es) | 2005-08-26 | 2007-11-14 | Chancellors Masters And Schola | Proceso para preparar acidos y lactonas sacarinicos |
| KR101238461B1 (ko) | 2005-12-09 | 2013-03-05 | 길리어드 파마셋 엘엘씨 | 항바이러스성 뉴클레오시드 |
| EP1976382B1 (en) | 2005-12-23 | 2013-04-24 | IDENIX Pharmaceuticals, Inc. | Process for preparing a synthetic intermediate for preparation of branched nucleosides |
| US7879815B2 (en) | 2006-02-14 | 2011-02-01 | Merck Sharp & Dohme Corp. | Nucleoside aryl phosphoramidates for the treatment of RNA-dependent RNA viral infection |
| US7951789B2 (en) | 2006-12-28 | 2011-05-31 | Idenix Pharmaceuticals, Inc. | Compounds and pharmaceutical compositions for the treatment of viral infections |
| US7964580B2 (en) | 2007-03-30 | 2011-06-21 | Pharmasset, Inc. | Nucleoside phosphoramidate prodrugs |
| US20100279969A1 (en) | 2007-05-14 | 2010-11-04 | Rfs Pharma, Llc | Azido purine nucleosides for treatment of viral infections |
| GB0718575D0 (en) | 2007-09-24 | 2007-10-31 | Angeletti P Ist Richerche Bio | Nucleoside derivatives as inhibitors of viral polymerases |
| US20090318380A1 (en) | 2007-11-20 | 2009-12-24 | Pharmasset, Inc. | 2',4'-substituted nucleosides as antiviral agents |
| HRP20150359T1 (hr) | 2008-04-23 | 2015-05-22 | Gilead Sciences, Inc. | 1'-supstituirani karba-nukleozidni analozi za antivirusnu terapiju |
| EP2476690A1 (en) | 2008-07-02 | 2012-07-18 | IDENIX Pharmaceuticals, Inc. | Compounds and pharmaceutical compositions for the treatment of viral infections |
| GB0815968D0 (en) | 2008-09-03 | 2008-10-08 | Angeletti P Ist Richerche Bio | Antiviral agents |
| GB0900914D0 (en) | 2009-01-20 | 2009-03-04 | Angeletti P Ist Richerche Bio | Antiviral agents |
| US7973013B2 (en) | 2009-09-21 | 2011-07-05 | Gilead Sciences, Inc. | 2'-fluoro substituted carba-nucleoside analogs for antiviral treatment |
| TWI515000B (zh) | 2010-04-01 | 2016-01-01 | 伊迪尼克製藥公司 | 用於治療病毒感染之化合物及醫藥組合物 |
| JP5891241B2 (ja) | 2010-12-20 | 2016-03-22 | ギリアード サイエンシーズ, インコーポレイテッド | Hcvを処置するための組合せ |
| CN103842369A (zh) | 2011-03-31 | 2014-06-04 | 埃迪尼克斯医药公司 | 用于治疗病毒感染的化合物和药物组合物 |
| EP2696679B1 (en) | 2011-04-13 | 2017-08-02 | Merck Sharp & Dohme Corp. | 2'-cyano substituted nucleoside derivatives and methods of use thereof for the treatment of viral diseases |
| JP2014515023A (ja) | 2011-04-13 | 2014-06-26 | メルク・シャープ・アンド・ドーム・コーポレーション | 2’−置換ヌクレオシド誘導体およびウイルス疾患の処置のためのその使用方法 |
| WO2012142075A1 (en) * | 2011-04-13 | 2012-10-18 | Merck Sharp & Dohme Corp. | 2'-azido substituted nucleoside derivatives and methods of use thereof for the treatment of viral diseases |
| US20140212382A1 (en) | 2011-05-19 | 2014-07-31 | Emory University | Purine monophosphate prodrugs for treatment of viral infections |
| US9403863B2 (en) | 2011-09-12 | 2016-08-02 | Idenix Pharmaceuticals Llc | Substituted carbonyloxymethylphosphoramidate compounds and pharmaceutical compositions for the treatment of viral infections |
| TW201331221A (zh) | 2011-10-14 | 2013-08-01 | Idenix Pharmaceuticals Inc | 嘌呤核苷酸化合物類之經取代的3’,5’-環磷酸酯及用於治療病毒感染之醫藥組成物 |
| HK1203514A1 (en) | 2012-05-22 | 2015-10-30 | Idenix Pharmaceuticals Llc | D-amino acid compounds for liver disease |
| EP2852604B1 (en) | 2012-05-22 | 2017-04-12 | Idenix Pharmaceuticals LLC | 3',5'-cyclic phosphoramidate prodrugs for hcv infection |
| US9296778B2 (en) | 2012-05-22 | 2016-03-29 | Idenix Pharmaceuticals, Inc. | 3′,5′-cyclic phosphate prodrugs for HCV infection |
| WO2014052638A1 (en) | 2012-09-27 | 2014-04-03 | Idenix Pharmaceuticals, Inc. | Esters and malonates of sate prodrugs |
| CN104936970A (zh) | 2012-10-08 | 2015-09-23 | 埃迪尼克斯医药公司 | 用于hcv感染的2′-氯核苷类似物 |
| AR092959A1 (es) | 2012-10-17 | 2015-05-06 | Merck Sharp & Dohme | Derivados de nucleosidos 2-metil sustituidos y metodos de uso de los mismos para el tratamiento de enfermedades virales |
| US9242988B2 (en) | 2012-10-17 | 2016-01-26 | Merck Sharp & Dohme Corp. | 2′-cyano substituted nucleoside derivatives and methods of use thereof for the treatment of viral diseases |
| US9457039B2 (en) | 2012-10-17 | 2016-10-04 | Merck Sharp & Dohme Corp. | 2′-disubstituted nucleoside derivatives and methods of use thereof for the treatment of viral diseases |
| EP2909223B1 (en) | 2012-10-19 | 2017-03-22 | Idenix Pharmaceuticals LLC | Dinucleotide compounds for hcv infection |
| WO2014066239A1 (en) | 2012-10-22 | 2014-05-01 | Idenix Pharmaceuticals, Inc. | 2',4'-bridged nucleosides for hcv infection |
| EP2938624A1 (en) | 2012-11-14 | 2015-11-04 | IDENIX Pharmaceuticals, Inc. | D-alanine ester of sp-nucleoside analog |
| EP2920195A1 (en) | 2012-11-14 | 2015-09-23 | IDENIX Pharmaceuticals, Inc. | D-alanine ester of rp-nucleoside analog |
| WO2014099941A1 (en) | 2012-12-19 | 2014-06-26 | Idenix Pharmaceuticals, Inc. | 4'-fluoro nucleosides for the treatment of hcv |
| WO2014137930A1 (en) | 2013-03-04 | 2014-09-12 | Idenix Pharmaceuticals, Inc. | Thiophosphate nucleosides for the treatment of hcv |
| US20140271547A1 (en) | 2013-03-13 | 2014-09-18 | Idenix Pharmaceuticals, Inc. | Amino acid phosphoramidate pronucleotides of 2'-cyano, azido and amino nucleosides for the treatment of hcv |
| WO2014165542A1 (en) | 2013-04-01 | 2014-10-09 | Idenix Pharmaceuticals, Inc. | 2',4'-fluoro nucleosides for the treatment of hcv |
| US10005779B2 (en) | 2013-06-05 | 2018-06-26 | Idenix Pharmaceuticals Llc | 1′,4′-thio nucleosides for the treatment of HCV |
| EP3010512B1 (en) | 2013-06-18 | 2017-12-27 | Merck Sharp & Dohme Corp. | Cyclic phosphonate substituted nucleoside derivatives and methods of use thereof for the treatment of viral diseases |
| WO2015017713A1 (en) | 2013-08-01 | 2015-02-05 | Idenix Pharmaceuticals, Inc. | D-amino acid phosphoramidate pronucleotides of halogeno pyrimidine compounds for liver disease |
-
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- 2001-05-23 IL IL15302001A patent/IL153020A0/xx unknown
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013079257A (ja) * | 2000-05-26 | 2013-05-02 | Idenix (Cayman) Ltd | フラビウイルスおよびペスチウイルス治療のための方法および組成物 |
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