tert-Butyl (2S)-2-{(3S)-3-[[(6-chloro-2-naphthyl)sulfonyl](methyl)amino]-2-oxopyrrolidin-1-yl}propanoate | 478645-77-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: tert-Butyl (2S)-2-{(3S)-3-[[(6-chloro-2-naphthyl)sulfonyl](methyl)amino]-2-oxopyrrolidin-1-yl}propanoate
• 英文别名: tert-butyl (2S)-2-[(3S)-3-[(6-chloronaphthalen-2-yl)sulfonyl-methylamino]-2-oxopyrrolidin-1-yl]propanoate
• CAS: 478645-77-1
• 化学式: C₂₂H₂₇ClN₂O₅S
• 分子量: 466.986
• InChiKey: INLIIFLTVFGVAZ-LIRRHRJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  92.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-Butyl (2S)-2-{(3S)-3-[[(6-chloro-2-naphthyl)sulfonyl](methyl)amino]-2-oxopyrrolidin-1-yl}propanoate 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Design and synthesis of orally active pyrrolidin-2-one-based factor Xa inhibitors

  摘要：

  A series of novel, non-basic 3-(6-chloronaphth-2-ylsulfonyl)aminopyrrolidin-2-one-based factor Xa (fXa) inhibitors, incorporating an alanylamide P4 group, was designed and synthesised. Within this series, the N-2-(morpholin-4-yl)-2-oxoethyl derivative 24 was shown to be a potent, selective fXa inhibitor with good anticoagulant activity. Moreover, 24 possessed highly encouraging rat and dog pharmacokinetic profiles with excellent oral bioavailabilities in both species. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.053
• 作为产物：
  描述：

  tert-butyl (2S)-2-((3S)-3-{[(benzyloxy)carbonyl]amino}-2-oxopyrrolidin-1-yl)propanoate 在 palladium on activated charcoal 吡啶 、 氢气 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醇 、 乙腈 为溶剂， 生成 tert-Butyl (2S)-2-{(3S)-3-[[(6-chloro-2-naphthyl)sulfonyl](methyl)amino]-2-oxopyrrolidin-1-yl}propanoate
  参考文献：
  名称：

  Design and synthesis of orally active pyrrolidin-2-one-based factor Xa inhibitors

  摘要：

  A series of novel, non-basic 3-(6-chloronaphth-2-ylsulfonyl)aminopyrrolidin-2-one-based factor Xa (fXa) inhibitors, incorporating an alanylamide P4 group, was designed and synthesised. Within this series, the N-2-(morpholin-4-yl)-2-oxoethyl derivative 24 was shown to be a potent, selective fXa inhibitor with good anticoagulant activity. Moreover, 24 possessed highly encouraging rat and dog pharmacokinetic profiles with excellent oral bioavailabilities in both species. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.053

文献信息

• Chemical compounds
  申请人：Chan Chuen

  公开号：US20060160886A1

  公开（公告）日：2006-07-20

  The invention relates to compounds of formula (Ic) processes for their preparation, pharmaceutical compositions containing them and to their use in medicine, particularly use in the amelioration of a clinical condition for which a Factor Xa inhibitor is indicated.

  本发明涉及式(Ic)化合物，其制备方法，含有它们的药物组合物以及它们在医学上的应用，特别是在改善适应于Xa因子抑制剂的临床状况方面的应用。
• Pyrrolidin-2-one derivatives as inhibitors of factor xa
  申请人：——

  公开号：US20040152697A1

  公开（公告）日：2004-08-05

  The invention relates to compounds of formula (Ic) processes for their preparation, pharmaceutical compositions containing them and to their use in medicine, particularly use in the amelioration of a clinical condition for which a Factor Xa inhibitor is indicated. 1

  本发明涉及公式（Ic）化合物，它们的制备过程，含有它们的药物组合物，以及它们在医学上的应用，特别是在改善适合使用因子Xa抑制剂的临床症状方面的应用。
• Pyrrolidin-2-one derivatives as inhibitors of factor Xa
  申请人：SmithKline Beecham Corporation

  公开号：US07084139B2

  公开（公告）日：2006-08-01

  The invention relates to compounds of formula (Ic) processes for their preparation, pharmaceutical compositions containing them and to their use in medicine, particularly use in the amelioration of a clinical condition for which a Factor Xa inhibitor is indicated.

  该发明涉及式(Ic)的化合物、制备它们的方法、含有它们的药物组合物以及它们在医学上的使用，特别是在改善适应于Xa因子抑制剂的临床状况方面的使用。
• US7282497B2
  申请人：——

  公开号：US7282497B2

  公开（公告）日：2007-10-16