替比夫定杂质 | 110508-94-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 中文名称: 替比夫定杂质
• 英文名称: β-L-arabinosylthymine
• 英文别名: 1-β-D-Arabinofuranosylthymin；1-β-L-arabinofuranosyl-5-methyl-1H-pyrimidine-2,4-dione；1-β-L-arabinofuranosylthymine；1-(beta-l-Arabinofuranosyl)thymine；1-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 110508-94-6
• 化学式: C₁₀H₁₄N₂O₆
• 分子量: 258.231
• InChiKey: DWRXFEITVBNRMK-LKHWLPBLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  119
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-(5'-O-trityl-β-L-arabinofuranosyl)thymine 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 生成 替比夫定杂质
  参考文献：
  名称：

  [DE] Beta-L-NUCLEOSIDE UND IHRE VERWENDUNG ALS PHARMAZEUTISCHE MITTEL ZUR BEHANDLUNG VIRALER ERKRANKUNGEN
  [EN] Beta-L-NUCLEOSIDES AND USE THEREOF AS PHARMACEUTICAL AGENTS FOR TREATING VIRAL DISEASES
  [FR] NUCLEOSIDES Beta-L ET LEUR UTILISATION COMME AGENTS PHARMACEUTIQUES POUR TRAITER DES AFFECTIONS VIRALES

  摘要：

  该发明涉及核苷类似物、核酸和包括它们的药物，以及利用核苷类似物、核酸和药物用于诊断、预防或治疗病毒、细菌、真菌和/或寄生虫感染或癌症，特别是肝炎感染的用途。该发明还涉及一种制备核苷类似物的方法，以及一种用于预防和治疗病毒性疾病，特别是肝炎感染的试剂盒及其用途。

  公开号：

  WO2005026186A1

文献信息

• PROCESS FOR PREPARING L-NUCLEIC ACID DERIVATIVES AND INTERMEDIATES THEREOF
  申请人：Cercus Jacques

  公开号：US20090018325A1

  公开（公告）日：2009-01-15

  A novel method has been found to produce 2,2′-anhydro-1-(β-L-arabinofuranosyl)thymine as a novel useful intermediate compound. A novel method has been further found to produce thymidine from 2,2′-anhydro-1-(β-L-arabinofuranosyl)thymine. According to these methods, synthesis of various L-nucleic acid derivatives, synthesis of which has been difficult till now, is possible.

  已找到一种新的方法，用于生产2,2′-去水-1-(β-L-阿拉伯呋喃糖基)胸腺嘧啶作为一种新的有用中间化合物。另外还发现了一种新的方法，可从2,2′-去水-1-(β-L-阿拉伯呋喃糖基)胸腺嘧啶中生产胸腺嘧啶。根据这些方法，合成各种L-核酸衍生物，这些衍生物的合成直到现在都很困难，现在是可能的。
• L-nucleic acid derivative and processes for the synthesis thereof
  申请人：——

  公开号：US20040063926A1

  公开（公告）日：2004-04-01

  A novel method has been found to produce 2,2′-anhydro-1-(&bgr;-L-arabinofuranosyl)thymine as a novel useful intermediate compound. A novel method has been further found to produce thymidine from 2,2′-anhydro-1-(&bgr;-L-arabinofuranosyl)thymine. A novel method has been further found to L-2′-deoxyribose derivatives as a useful synthetic intermediate through L-2,2′-anhydro-5,6-dihydrocyclouridine derivative. According to these methods, synthesis of various L-nucleic acid derivatives, synthesis of which has been difficult till now.

  已经发现了一种新的方法来生产2,2'-去氧-1-(&bgr;-L-阿拉伯呋喃糖基)胸腺嘧啶作为一种新的有用中间化合物。进一步发现了一种新的方法来从2,2'-去氧-1-(&bgr;-L-阿拉伯呋喃糖基)胸腺嘧啶中生产胸腺嘧啶。另外，还发现了一种新的方法，通过L-2,2'-去氧-5,6-二氢环尿嘧啶衍生物来生产L-2'-脱氧核糖衍生物作为有用的合成中间体。根据这些方法，合成各种L-核酸衍生物，这些衍生物的合成迄今为止一直很困难。
• Beta-L-nucleosides and use thereof as pharmaceutical agents for the treatment of viral diseases
  申请人：Matthes Eckart

  公开号：US20060217345A1

  公开（公告）日：2006-09-28

  Nucleoside analogs, nucleic acids and pharmaceutical agents comprising same, and to the use of said nucleoside analogs, nucleic acids and pharmaceutical agents in the diagnosis, prophylaxis or therapy of a viral, bacterial, fungicidal and/or parasitic infection, or of cancer, particularly of hepatitis infections. The invention also relates to a method for the preparation of said nucleoside analogs and to a kit and the use thereof in the prophylaxis and therapy of viral diseases, particularly of hepatitis infections. As stated in 37 C.F.R. §1.72(b): A brief abstract of the technical disclosure in the specification must commence on a separate sheet, preferably following the claims, under the heading “Abstract of the Disclosure.” The purpose of the abstract is to enable the Patent and Trademark Office and the public generally to determine quickly from a cursory inspection the nature and gist of the technical disclosure. The abstract shall not be used for interpreting the scope of the claims. Therefore, any statements made relating to the abstract are not intended to limit the claims in any manner and should not be interpreted as limiting the claims in any manner.

  本发明涉及核苷类似物、核酸和含有它们的药物剂，以及将上述核苷类似物、核酸和药物剂用于病毒、细菌、真菌和/或寄生虫感染或癌症，特别是肝炎感染的诊断、预防或治疗。本发明还涉及一种制备上述核苷类似物的方法，以及一种用于病毒性疾病，特别是肝炎感染的预防和治疗的工具箱及其使用方法。根据37 C.F.R. §1.72(b)规定：技术规范说明书中的简要摘要必须在单独的一页上开始，优选在声明后面，标题为“技术披露摘要”。摘要的目的是让专利和商标局以及公众通过粗略的检查，快速确定技术披露的本质和要点。摘要不得用于解释权利要求的范围。因此，与摘要相关的任何声明均不意在以任何方式限制权利要求，并且不应被解释为以任何方式限制权利要求。
• L-Nucleosides for the treatment of hepatitis B-virus and Epstein-barr virus
  申请人：THE UNIVERSITY OF GEORGIA RESEARCH FOUNDATION, INC.

  公开号：EP1283211A2

  公开（公告）日：2003-02-12

  A method for the treatment of a host, and in particular, a human, infected with HBV or EBV is provided that includes administering an HBV- or EBV- treatment amount of an L-nucleoside of formula (I) wherein R is a purine or pyrimidine base. In one preferred embodiment, the active compound is 2'-fluoro-5-methyl-β-L-arabinofuranosyluridine (also referred to as L-FMAU) This compound is a potent antiviral agent against HBV and EBV and exhibits low cytotoxicity. Other specific examples of active compounds include N1-(2'-deoxy-2'-fluoro-β-L-arabinofuranosyl)-5-ethyluracil, N1-(2'-deoxy-2'-fluoro-β-L-arabinofuranosyl)-5-iodocytosine), and N1-(2'-deoxy-2'-fluoro-β-L-arabinofuranosyl)-5-iodouracil.

  提供了一种治疗感染 HBV 或 EBV 的宿主，特别是人类的方法，该方法包括施用 HBV 或 EBV 治疗量的式（I）的 L-核苷。 其中 R 是嘌呤或嘧啶碱。在一个优选的实施方案中，活性化合物是 2'-氟-5-甲基-β-L-阿拉伯呋喃糖基尿苷（也称为 L-FMAU），该化合物是一种抗 HBV 和 EBV 的强效抗病毒剂，细胞毒性低。其他活性化合物的具体例子包括 N1-(2'-脱氧-2'-氟-β-L-阿拉伯呋喃糖基)-5-乙基尿嘧啶、N1-(2'-脱氧-2'-氟-β-L-阿拉伯呋喃糖基)-5-碘胞嘧啶和 N1-(2'-脱氧-2'-氟-β-L-阿拉伯呋喃糖基)-5-碘尿嘧啶。
• L-NUCLEIC ACID DERIVATIVES AND PROCESSES FOR THE SYNTHESIS THEREOF
  申请人：Mitsui Chemicals, Inc.

  公开号：EP1348712A1

  公开（公告）日：2003-10-01

  A novel method has been found to produce 2,2'-anhydro-1-(β-L-arabinofuranosyl)thymine as a novel useful intermediate compound. A novel method has been further found to produce thymidine from 2,2'-anhydro-1-(β-L-arabinofuranosyl)thymine. A novel method has been further found to L-2'-deoxyribose derivatives as a useful synthetic intermediate through L-2,2'-anhydro-5,6-dihydrocyclouridine derivative. According to these methods, synthesis of various L-nucleic acid derivatives, synthesis of which has been difficult till now.

  发现了一种生产 2,2'-脱水-1-(β-L-阿拉伯呋喃糖基)胸腺嘧啶这种新型有用中间化合物的新方法。还发现了一种从 2,2'-脱水-1-(β-L-阿拉伯呋喃糖基)胸腺嘧啶生产胸腺嘧啶的新方法。通过 L-2,2'-脱氢-5,6-二氢环尿苷衍生物，还发现了一种将 L-2'- 脱氧核糖衍生物作为有用合成中间体的新方法。根据这些方法，可以合成各种 L-核酸衍生物。