5-amino-7-thioxo-3-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-thiazolo[4,5-d]pyrimidin-2-one | 847453-45-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 5-amino-7-thioxo-3-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-thiazolo[4,5-d]pyrimidin-2-one
• 英文别名: 5-Amino-7-thioxo-3-(2,3,5'-tri-O-acetyl-beta-D-ribofuranosyl)-thiazolo[4,5-d]pyrimidin-2-one；[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(5-amino-2-oxo-7-sulfanylidene-4H-[1,3]thiazolo[4,5-d]pyrimidin-3-yl)oxolan-2-yl]methyl acetate
• CAS: 847453-45-6
• 化学式: C₁₆H₁₈N₄O₈S₂
• 分子量: 458.473
• InChiKey: KXGPIRQYCRLUCM-NZHONMPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  216
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  5-amino-7-thioxo-3-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-thiazolo[4,5-d]pyrimidin-2-one 在 镍 咪唑 、 氢氟酸 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 DMF (N,N-dimethylformamide) 、 丙酮 、 乙腈 为溶剂， 反应 30.08h， 生成 (2R,3R,4R,5R)-2-(hydroxymethyl)-5-(5-amino-2-oxothiazolo[4,5-d]pyrimidin-3(2H)-yl)tetrahydrofuran-3,4-diyl diacetate
  参考文献：
  名称：

  [EN] 3-beta-D-RIBOFURANOSYLTHIAZOLO[4,5-d]PYRIDIMINE NUCLEOSIDES AND USES THEREOF
  [FR] NUCLEOSIDES 3-20051222WO03045968A1ANADYS PHARMACEUTICALS INC [US]20030605WX1-20XUS5041426AROBINS ROLAND K [US], et al19910820compounds 6,7,41,42X1,2,12XWO03045968A1ANADYS PHARMACEUTICALS INC [US]20030605"Remington's Pharmaceutical Sciences"Remington's Pharmaceutical SciencesBARANOV ET AL., CHEM. HET. COMPOUNDS, vol. 11, 1975, pages 73BARANOV ET AL.CHEM. HET. COMPOUNDS19751173

  摘要：

  本发明涉及3-ß-D-核糖呋喃噻唑[4,5-d]吡啶嘧啶核苷和含有此类化合物的药物组合物，具有免疫调节活性。本发明还涉及这类化合物和组合物的治疗或预防用途，以及通过给予这类化合物的有效剂量来治疗本文所述的疾病和疾病的方法。

  公开号：

  WO2005121162A1
• 作为产物：
  描述：

  [(2R,3R,4R,5R)-4-乙酰氧基-5-(乙酰氧基甲基)-2-(5-氨基-2,7-二氧代-4H-[1,3]噻唑并[5,4-e]嘧啶-3-基)四氢呋喃-3-基]乙酸酯 在 P₂S₅ 作用下， 以 吡啶 、 水 为溶剂， 以0.93 g (90%)的产率得到5-amino-7-thioxo-3-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-thiazolo[4,5-d]pyrimidin-2-one
  参考文献：
  名称：

  3-B-D-ribofuranosylthiazolo [4,5-d] pyridimine nucleosides and uses thereof

  摘要：

  这项发明涉及3-β-D-核糖呋喃基噻唑并[4,5-d]吡啶嘧啶核苷及含有这种化合物的具有免疫调节活性的药物组合物。该发明还涉及这种化合物和组合物的治疗或预防用途，以及通过给予这种化合物的有效量来治疗本文描述的疾病和紊乱的方法。

  公开号：

  US20050070556A1

文献信息

• Administration of TLR7 ligands and prodrugs thereof for treatment of infection by hepatitis C virus
  申请人：Averett R. Devron

  公开号：US20050054590A1

  公开（公告）日：2005-03-10

  This invention relates to methods for treating or preventing hepatitis C virus infections in mammals using Toll-Like Receptor (TLR)7 ligands and prodrugs thereof. More particularly, this invention relates to methods of orally administering a therapeutically effective amount of one or more prodrugs of TLR7 ligands for the treatment or prevention of hepatitis C viral infection. Oral administration of these TLR7 immunomodulating ligands and prodrugs thereof to a mammal provides therapeutically effective amounts and reduced undesirable side effects.

  这项发明涉及使用Toll样受体（TLR）7配体及其前药治疗或预防哺乳动物体内的丙型肝炎病毒感染的方法。更具体地，这项发明涉及口服给予一种或多种TLR7配体前药的治疗有效量，用于治疗或预防丙型肝炎病毒感染。将这些TLR7免疫调节配体及其前药口服给哺乳动物可提供治疗有效量并减少不良副作用。
• 3-Beta-D-Ribofuranosylthiazolo[ 4,5-D] Pyridimine Nucleosides and Uses Thereof
  申请人：Averett Devron R.

  公开号：US20080070852A1

  公开（公告）日：2008-03-20

  The invention is directed to 3-β-D-ribofuranosylthiazolo[4,5-d]pyrimidine nucleosides and pharmaceutical compositions containing such compounds that have immunomodulatory activity. The invention is also directed to the therapeutic or prophylactic use of such compounds and compositions, and to methods of treating diseases and disorders described herein, by administering effective amounts of such compounds.

  本发明涉及3-β-D-核糖呋喃基噻唑[4,5-d]嘧啶核苷及含有这种化合物的药物组合物，其具有免疫调节活性。本发明还涉及使用这种化合物和组合物进行治疗或预防，以及通过给予有效剂量的这种化合物来治疗本文所述的疾病和障碍的方法。
• 3-B-D-RIBOFURANOSYLTHIAZOLO[4,5-d]PYRIMIDINE NUCLEOSIDES AND USES THEREOF
  申请人：Averet Devron R.

  公开号：US20080255063A1

  公开（公告）日：2008-10-16

  The invention is directed to 3-β-D-ribofuranosylthiazolo[4,5-d]pyrimidine nucleosides and pharmaceutical compositions containing such compounds that have immunomodulatory activity. The invention is also directed to the therapeutic or prophylactic use of such compounds and compositions, and to methods of treating diseases and disorders described herein, by administering effective amounts of such compounds.

  本发明涉及3-β-D-核糖呋喃噻唑并[4,5-d]嘧啶核苷及含有这种化合物的制药组合物，该化合物具有免疫调节活性。本发明还涉及使用这种化合物和组合物的治疗或预防用途，以及通过给予有效剂量的这种化合物来治疗本文所述的疾病和障碍的方法。
• 3-B-D-ribofuranosylthiazolo [4,5-d] pyrimidine nucleosides and uses thereof
  申请人：Anadys Pharmaceuticals, Inc.

  公开号：US07321033B2

  公开（公告）日：2008-01-22

  The invention is directed to 3-β-D-ribofuranosylthiazolo[4,5-d]pyridimine nucleosides and pharmaceutical compositions containing such compounds that have immunomodulatory activity. The invention is also directed to the therapeutic or prophylactic use of such compounds and compositions, and to methods of treating diseases and disorders described herein, by administering effective amounts of such compounds.

  本发明涉及3-β-D-核糖呋喃基噻唑并[4,5-d]吡啶嘧啶核苷及含有这种化合物的药物组合物，具有免疫调节活性。本发明还涉及使用这种化合物和组合物的治疗或预防用途，并通过给予有效量的这种化合物的方法来治疗本文所述的疾病和障碍。
• ADMINISTRATION OF TLR7 LIGANDS AND PRODRUGS THEREOF FOR TREATMENT OF INFECTION BY HEPATITIS C VIRUS
  申请人：Averett Devron R.

  公开号：US20090298863A1

  公开（公告）日：2009-12-03

  This invention relates to methods for treating or preventing hepatitis C virus infections in mammals using Toll-Like Receptor (TLR)7 ligands and prodrugs thereof. More particularly, this invention relates to methods of orally administering a therapeutically effective amount of one or more prodrugs of TLR7 ligands for the treatment or prevention of hepatitis C viral infection. Oral administration of these TLR7 immunomodulating ligands and prodrugs thereof to a mammal provides therapeutically effective amounts and reduced undesirable side effects.

  本发明涉及使用Toll样受体(TLR)7配体及其前药治疗或预防哺乳动物的丙型肝炎病毒感染的方法。更具体地说，本发明涉及口服治疗丙型肝炎病毒感染的一种或多种TLR7配体前药的治疗剂量的方法。将这些TLR7免疫调节配体及其前药口服给哺乳动物，可提供治疗有效量和减少不良副作用。