CN1420779A - 甲脒修饰的二环碱核苷类似物 - Google Patents
甲脒修饰的二环碱核苷类似物 Download PDFInfo
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| US7056895B2 (en) * | 2000-02-15 | 2006-06-06 | Valeant Pharmaceuticals International | Tirazole nucleoside analogs and methods for using same |
| US7638496B2 (en) * | 2000-02-15 | 2009-12-29 | Valeant Pharmaceuticals North America | Nucleoside analogs with carboxamidine modified monocyclic base |
| MY164523A (en) * | 2000-05-23 | 2017-12-29 | Univ Degli Studi Cagliari | Methods and compositions for treating hepatitis c virus |
| EA007867B1 (ru) * | 2000-05-26 | 2007-02-27 | Айденикс (Кайман) Лимитед | Композиции для лечения флавивирусных и пестивирусных инфекций и способы их применения |
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| MXPA04012802A (es) | 2002-06-28 | 2005-04-19 | Idenix Cayman Ltd | Ester 2'-c-metil-3'-o-l-valina de ribofuranosil-citidina para el tratamiento de infecciones por flaviviridae. |
| 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 |
| EP1576138B1 (en) | 2002-11-15 | 2017-02-01 | Idenix Pharmaceuticals LLC. | 2'-methyl nucleosides in combination with interferon and flaviviridae mutation |
| CA2509687C (en) | 2002-12-12 | 2012-08-14 | Idenix (Cayman) Limited | Process for the production of 2'-branched nucleosides |
| WO2004084796A2 (en) * | 2003-03-28 | 2004-10-07 | Pharmasset Ltd. | Compounds for the treatment of flaviviridae infections |
| US20040197287A1 (en) * | 2003-04-04 | 2004-10-07 | The Procter & Gamble Company | Personal care composition containing an antidandruff component and a nonionic surfactant |
| US20040202636A1 (en) * | 2003-04-11 | 2004-10-14 | Kaczvinsky Joseph Robert | Personal care composition containing an antidandruff component and a nonionic surfactant |
| US20040197292A1 (en) * | 2003-04-04 | 2004-10-07 | The Procter & Gamble Company | Personal care composition containing an antidandruff component and a nonionic surfactant |
| US6930093B2 (en) * | 2003-07-10 | 2005-08-16 | Valeant Research & Development | Use of ribofuranose derivatives against inflammatory bowel diseases |
| US20050009848A1 (en) * | 2003-07-10 | 2005-01-13 | Icn Pharmaceuticals Switzerland Ltd. | Use of antivirals against inflammatory bowel diseases |
| WO2005018330A1 (en) * | 2003-08-18 | 2005-03-03 | Pharmasset, Inc. | Dosing regimen for flaviviridae therapy |
| US20050095218A1 (en) * | 2003-10-29 | 2005-05-05 | The Procter & Gamble Company | Personal care composition containing a detersive surfactant, an antidandruff component, and ketoamide surfactants |
| 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 |
| JP4516863B2 (ja) * | 2005-03-11 | 2010-08-04 | 株式会社ケンウッド | 音声合成装置、音声合成方法及びプログラム |
| US7879797B2 (en) | 2005-05-02 | 2011-02-01 | Merck Sharp & Dohme Corp. | HCV NS3 protease inhibitors |
| US7470664B2 (en) | 2005-07-20 | 2008-12-30 | Merck & Co., Inc. | HCV NS3 protease inhibitors |
| AU2006275605B2 (en) | 2005-08-01 | 2011-01-06 | Merck Sharp & Dohme Corp. | Macrocyclic peptides as HCV NS3 protease inhibitors |
| US7781576B2 (en) | 2005-12-23 | 2010-08-24 | Idenix Pharmaceuticals, Inc. | Process for preparing a synthetic intermediate for preparation of branched nucleosides |
| AU2006342447B2 (en) * | 2005-12-28 | 2013-06-20 | Translational Therapeutics, Inc | Translational dysfunction based therapeutics |
| US8497292B2 (en) | 2005-12-28 | 2013-07-30 | Translational Therapeutics, Inc. | Translational dysfunction based therapeutics |
| GB0609492D0 (en) | 2006-05-15 | 2006-06-21 | Angeletti P Ist Richerche Bio | Therapeutic agents |
| GB0612423D0 (en) | 2006-06-23 | 2006-08-02 | Angeletti P Ist Richerche Bio | Therapeutic agents |
| US7842672B2 (en) | 2006-07-07 | 2010-11-30 | Gilead Sciences, Inc. | Phosphonate inhibitors of HCV |
| AU2007309546A1 (en) | 2006-10-24 | 2008-05-02 | Istituto Di Ricerche Di Biologia Molecolare P. Angeletti S.P.A. | HCV NS3 protease inhibitors |
| CA2667266C (en) | 2006-10-24 | 2015-11-24 | Merck & Co., Inc. | Hcv ns3 protease inhibitors |
| EP2079479B1 (en) | 2006-10-24 | 2014-11-26 | Merck Sharp & Dohme Corp. | Hcv ns3 protease inhibitors |
| WO2008057208A2 (en) | 2006-10-27 | 2008-05-15 | Merck & Co., Inc. | Hcv ns3 protease inhibitors |
| EP2086982B1 (en) | 2006-10-27 | 2018-08-29 | Merck Sharp & Dohme Corp. | Hcv ns3 protease inhibitors |
| CN103224506A (zh) | 2006-12-20 | 2013-07-31 | P.安杰莱蒂分子生物学研究所 | 抗病毒的吲哚 |
| GB0625349D0 (en) | 2006-12-20 | 2007-01-31 | Angeletti P Ist Richerche Bio | Therapeutic compounds |
| GB0625345D0 (en) | 2006-12-20 | 2007-01-31 | Angeletti P Ist Richerche Bio | Therapeutic compounds |
| EP2178885A1 (en) | 2007-07-17 | 2010-04-28 | Istituto Di Ricerche Di Biologia Molecolare P. Angeletti S.P.A. | Macrocyclic indole derivatives for the treatment of hepatitis c infections |
| AU2008277377B2 (en) | 2007-07-19 | 2013-08-01 | Msd Italia S.R.L. | Macrocyclic compounds as antiviral agents |
| WO2009134624A1 (en) | 2008-04-28 | 2009-11-05 | Merck & Co., Inc. | Hcv ns3 protease inhibitors |
| SI2310095T1 (sl) | 2008-07-22 | 2013-01-31 | Merck Sharp & Dohme Corp. | Makrocikliäśne kuinoksalinske spojine kot hcv ns3 proteazni inhibitorji |
| 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 |
| WO2011014487A1 (en) | 2009-07-30 | 2011-02-03 | Merck Sharp & Dohme Corp. | Hepatitis c virus ns3 protease inhibitors |
| US9328138B2 (en) | 2011-11-15 | 2016-05-03 | Msd Italia S.R.L. | HCV NS3 protease inhibitors |
| US20140356325A1 (en) | 2012-01-12 | 2014-12-04 | Ligand Pharmaceuticals Incorporated | Novel 2'-c-methyl nucleoside derivative compounds |
| CN102978264B (zh) * | 2012-11-14 | 2014-12-10 | 广东肇庆星湖生物科技股份有限公司 | 一种他立韦林的制备方法 |
| 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 |
| US10449210B2 (en) | 2014-02-13 | 2019-10-22 | Ligand Pharmaceuticals Inc. | Prodrug compounds and their uses |
| EP3164136A4 (en) | 2014-07-02 | 2018-04-04 | Ligand Pharmaceuticals, Inc. | Prodrug compounds and uses therof |
| JP2018523665A (ja) | 2015-08-06 | 2018-08-23 | キメリックス インコーポレイテッド | 抗ウイルス剤として有用なピロロピリミジンヌクレオシドおよびその類縁体 |
| WO2019060692A1 (en) | 2017-09-21 | 2019-03-28 | Chimerix, Inc. | MORPHIC FORMS OF 4-AMINO-7- (3,4-DIHYDROXY-5- (HYDROXYMETHYL) -ETRAHYDROFURAN-2-YL) -2-METHYL-7H-PYRROLO [2,3-D] PYRIMIDINE-5-CARBOXAMIDE AND THEIR USES |
| CN111788196A (zh) | 2018-01-09 | 2020-10-16 | 配体药物公司 | 缩醛化合物及其治疗用途 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3984396A (en) | 1971-06-01 | 1976-10-05 | Icn Pharmaceuticals, Inc. | 1-(β,-D-ribofuranosyl)-1,2,4-triazole acid esters |
| USRE29835E (en) | 1971-06-01 | 1978-11-14 | Icn Pharmaceuticals | 1,2,4-Triazole nucleosides |
| US3991078A (en) | 1971-06-01 | 1976-11-09 | Icn Pharmaceuticals, Inc. | N-substituted 1,2,4-triazoles |
| US3798209A (en) | 1971-06-01 | 1974-03-19 | Icn Pharmaceuticals | 1,2,4-triazole nucleosides |
| US3962211A (en) * | 1975-01-13 | 1976-06-08 | The University Of Utah | 7-substituted nucleoside compounds |
| US4093624A (en) | 1977-01-31 | 1978-06-06 | Icn Pharmaceuticals, Inc. | 1,2,4-Thiadiazolidine-3,5-dione |
| SU1124559A1 (ru) * | 1983-06-08 | 1986-07-07 | Институт молекулярной биологии АН СССР | 1-(2-Оксиэтоксиметил)-1,2,4-триазол-5-карбоксамид,обладающий активностью противвируса герпеса |
| JPS6426593A (en) | 1987-07-21 | 1989-01-27 | Asahi Glass Co Ltd | Nucleoside derivative |
| US4892865A (en) * | 1987-12-01 | 1990-01-09 | The Regents Of The University Of Michigan | Pyrrolo[2,3-d]pyrimidine nucleosides as antiviral agents |
| US5405837A (en) * | 1993-05-18 | 1995-04-11 | Indiana University Foundation | Method for the treatment of neoplastic disease utilizing tiazofurin and ribavirin |
| UA46815C2 (uk) * | 1996-01-23 | 2002-06-17 | Ай-Сі-Ен Фармасьютикалз, Інк. | Спосіб модуляції реакції тн1 і тн2 в активованих т-клітинах людини, спосіб лікування пацієнта, спосіб лікування захворювання |
| US5767097A (en) * | 1996-01-23 | 1998-06-16 | Icn Pharmaceuticals, Inc. | Specific modulation of Th1/Th2 cytokine expression by ribavirin in activated T-lymphocytes |
| JP2002503212A (ja) * | 1996-10-16 | 2002-01-29 | アイ・シー・エヌ・フアーマシユーテイカルズ・インコーポレイテツド | 単環式ヌクレオシド、その類似体および使用 |
| HRP20020163A2 (en) * | 1999-08-27 | 2004-02-29 | Icn Pharmaceuticals | PYRROLO[2,3-d]PYRIMIDINE NUCLEOSIDE ANALOGS |
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