ethyl (3R,4R)-4-[(4-chlorophenyl)carbamoyl]pyrrolidine-3-carboxylate | 865528-41-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl (3R,4R)-4-[(4-chlorophenyl)carbamoyl]pyrrolidine-3-carboxylate
• CAS: 865528-41-2
• 化学式: C₁₄H₁₇ClN₂O₃
• 分子量: 296.754
• InChiKey: WYYBGNBHACUQPO-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (3R,4R)-4-[(4-chlorophenyl)carbamoyl]pyrrolidine-3-carboxylate 、 甲基磺酰氯 在 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以55%的产率得到(3R,4R)-4-(4-chlorophenylcarbamoyl)-1-methanesulfonylpyrrolidine-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Discovery of a factor Xa inhibitor (3R,4R)-1-(2,2-difluoro-ethyl)-pyrrolidine-3,4-dicarboxylic acid 3-[(5-chloro-pyridin-2-yl)-amide] 4-{[2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-phenyl]-amide} as a clinical candidate

  摘要：

  A series of (3R,4R)-pyrrolidine-3,4-dicarboxylic acid amides was investigated with respect to their factor Xa inhibitory activity, selectivity, pharmacokinetic properties, and ex vivo antithrombotic activity. The clinical candidate from this series, R1663, exhibits excellent selectivity against a panel of serine proteases and good pharmacokinetic properties in rats and monkeys. A Phase I clinical study with R1663 has been finalized.

  DOI：

  10.1016/j.bmcl.2010.06.126
• 作为产物：
  描述：

  (3R,4R)-4-(4-chlorophenylcarbamoyl)pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester 在 盐酸 、 水 作用下， 以 异丙醇 为溶剂， 反应 24.0h， 以100%的产率得到ethyl (3R,4R)-4-[(4-chlorophenyl)carbamoyl]pyrrolidine-3-carboxylate
  参考文献：
  名称：

  Discovery of a factor Xa inhibitor (3R,4R)-1-(2,2-difluoro-ethyl)-pyrrolidine-3,4-dicarboxylic acid 3-[(5-chloro-pyridin-2-yl)-amide] 4-{[2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-phenyl]-amide} as a clinical candidate

  摘要：

  A series of (3R,4R)-pyrrolidine-3,4-dicarboxylic acid amides was investigated with respect to their factor Xa inhibitory activity, selectivity, pharmacokinetic properties, and ex vivo antithrombotic activity. The clinical candidate from this series, R1663, exhibits excellent selectivity against a panel of serine proteases and good pharmacokinetic properties in rats and monkeys. A Phase I clinical study with R1663 has been finalized.

  DOI：

  10.1016/j.bmcl.2010.06.126

文献信息

• Discovery of a factor Xa inhibitor (3R,4R)-1-(2,2-difluoro-ethyl)-pyrrolidine-3,4-dicarboxylic acid 3-[(5-chloro-pyridin-2-yl)-amide] 4-{[2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-phenyl]-amide} as a clinical candidate
  作者：Lilli Anselm、David W. Banner、Jörg Benz、Katrin Groebke Zbinden、Jacques Himber、Hans Hilpert、Walter Huber、Bernd Kuhn、Jean-Luc Mary、Michael B. Otteneder、Narendra Panday、Fabienne Ricklin、Martin Stahl、Stefan Thomi、Wolfgang Haap

  DOI：10.1016/j.bmcl.2010.06.126

  日期：2010.9

  A series of (3R,4R)-pyrrolidine-3,4-dicarboxylic acid amides was investigated with respect to their factor Xa inhibitory activity, selectivity, pharmacokinetic properties, and ex vivo antithrombotic activity. The clinical candidate from this series, R1663, exhibits excellent selectivity against a panel of serine proteases and good pharmacokinetic properties in rats and monkeys. A Phase I clinical study with R1663 has been finalized.