(3R,4R,5S)-4-acetamido-5-[N-(N'-hydroxy)guanidino]-3-(1-ethylpropoxy)cyclohex-1-en-1-carboxylic acid ethyl ester | 1431974-63-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (3R,4R,5S)-4-acetamido-5-[N-(N'-hydroxy)guanidino]-3-(1-ethylpropoxy)cyclohex-1-en-1-carboxylic acid ethyl ester
• 英文别名: (3R,4R,5S)-ethyl 4-acetamido-5-(N-(N′-hydroxy)guanidine)-3-(1-ethylpropoxy)cyclohex-1-enecarboxylate
• CAS: 1431974-63-8
• 化学式: C₁₇H₃₀N₄O₅
• 分子量: 370.4
• InChiKey: DAKYBSAHWDBGLY-RRFJBIMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  135
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  奥司他韦 生成 (3R,4R,5S)-4-acetamido-5-[N-(N'-hydroxy)guanidino]-3-(1-ethylpropoxy)cyclohex-1-en-1-carboxylic acid ethyl ester
  参考文献：
  名称：

  摘要：

  DOI：

文献信息

• 神经氨酸苷酶抑制剂的前药及其组合物和用途
  申请人：北京普禄德医药科技有限公司

  公开号：CN103848762B

  公开（公告）日：2016-08-31

  本发明提供了一种式Ia所示的化合物或其药物可接受的盐、溶剂化物、多晶型体、对映体或外消旋混合物，该化合物作为神经氨酸苷酶抑制剂的前药，可以改善神经氨酸苷酶抑制剂的体内半衰期。本发明还提供了所述化合物的制备方法、包含所述化合物的药物组合物、以及所述化合物和药物组合物在制备神经氨酸苷酶抑制剂类药物和治疗相关疾病中的用途。
• COMPOUNDS FOR THE TREATMENT OF INFLUENZA
  申请人：CHRISTIAN-ALBRECHTS-UNIVERSITAT ZU KIEL

  公开号：US20140288312A1

  公开（公告）日：2014-09-25

  The invention relates to oseltamivir derivatives as influenza neuraminidase inhibitors for treating influenza infections and to a method for producing said compounds.

  本发明涉及奥司他韦衍生物作为治疗流感感染的流感神经氨酸酶抑制剂，以及制备该化合物的方法。
• Development of Novel Potent Orally Bioavailable Oseltamivir Derivatives Active against Resistant Influenza A
  作者：Dennis Schade、Joscha Kotthaus、Lukas Riebling、Jürke Kotthaus、Helge Müller-Fielitz、Walter Raasch、Oliver Koch、Nora Seidel、Michaela Schmidtke、Bernd Clement

  DOI：10.1021/jm401492x

  日期：2014.2.13

  With the emergence of oseltamivir-resistant influenza viruses and in view of a highly pathogenic flu pandemic, it is important to develop new anti-influenza agents. Here, the development of neuraminidase (NA) inhibitors that were designed to overcome resistance mechanisms along with unfavorable pharmacokinetic (PK) properties is described. Several 5-guanidino- and 5-amidino-based oseltamivir derivatives were synthesized and profiled for their anti-influenza activity and in vitro and in vivo PK properties. Amidine 6 and guanidine 7 were comparably effective against a panel of different A/H1N1 and A/H3N2 strains and also inhibited mutant A/H1N1 neuraminidase. Among different prodrug strategies pursued, a simple amidoxime ethyl ester (9) exhibited a superior PK profile with an oral bioavailability of 31% (rats), which is comparable to oseltamivir (36%). Thus, bioisosteric replacement of the 5-guanidine with an acetamidine-in the form of its N-hydroxy prodrug-successfully tackled the two key limitations of currently used NA inhibitors, as exemplified with oseltamivir.
• VERBINDUNGEN ZUR THERAPIE DER INFLUENZA
  申请人：Christian-Albrechts-Universität zu Kiel

  公开号：EP2771316B1

  公开（公告）日：2019-10-16
• US9828333B2
  申请人：——

  公开号：US9828333B2

  公开（公告）日：2017-11-28