1-(5-butyryl-3-cyano-6-methylpyridin-2-yl)piperidine-4-carboxylic acid | 1204588-80-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-(5-butyryl-3-cyano-6-methylpyridin-2-yl)piperidine-4-carboxylic acid
• 英文别名: 1-(5-Butanoyl-3-cyano-6-methylpyridin-2-yl)piperidine-4-carboxylic acid
• CAS: 1204588-80-6
• 化学式: C₁₇H₂₁N₃O₃
• 分子量: 315.372
• InChiKey: ZNKKZPNFNQFDCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  94.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(5-butyryl-3-cyano-6-methylpyridin-2-yl)piperidine-4-carboxylic acid 、 苯甲磺酰胺 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-(benzylsulfonyl)-1-(5-butyryl-3-cyano-6-methylpyridin-2-yl)piperidine-4-carboxamide
  参考文献：
  名称：

  Optimization of ketone-based P2Y12 receptor antagonists as antithrombotic agents: Pharmacodynamics and receptor kinetics considerations

  摘要：

  Modification of a series of P2Y(12) receptor antagonists by replacement of the ester functionality was aimed at minimizing the risk of in vivo metabolic instability and pharmacokinetic variability. The resulting ketones were then optimized for their P2Y(12) antagonistic and anticoagulation effects in combination with their physicochemical and absorption profiles. The most promising compound showed very potent antiplatelet action in vivo. However, pharmacodynamic-pharmacokinetic analysis did not reveal a significant separation between its anti-platelet and bleeding effects. The relevance of receptor binding kinetics to the in vivo profile is described. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.001
• 作为产物：
  描述：

  6-(4-(tert-butoxycarbonyl)piperidin-1-yl)-5-cyano-2-methylnicotinic acid 在 草酰氯 、 iron(III)-acetylacetonate 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.33h， 生成 1-(5-butyryl-3-cyano-6-methylpyridin-2-yl)piperidine-4-carboxylic acid
  参考文献：
  名称：

  Optimization of ketone-based P2Y12 receptor antagonists as antithrombotic agents: Pharmacodynamics and receptor kinetics considerations

  摘要：

  Modification of a series of P2Y(12) receptor antagonists by replacement of the ester functionality was aimed at minimizing the risk of in vivo metabolic instability and pharmacokinetic variability. The resulting ketones were then optimized for their P2Y(12) antagonistic and anticoagulation effects in combination with their physicochemical and absorption profiles. The most promising compound showed very potent antiplatelet action in vivo. However, pharmacodynamic-pharmacokinetic analysis did not reveal a significant separation between its anti-platelet and bleeding effects. The relevance of receptor binding kinetics to the in vivo profile is described. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.001

文献信息

• [EN] 2-AMINO-6-ALKYL SUBSTITUTED PYRIDINE DERIVATIVES USEFUL AS P2Y12 INHIBITORS 308<br/>[FR] DÉRIVÉS DE PYRIDINE SUBSTITUÉS PAR 2-AMINO-6-ALKYLE UTILES COMME INHIBITEURS DE P2Y12
  申请人：ASTRAZENECA AB

  公开号：WO2010005385A1

  公开（公告）日：2010-01-14

  The present invention relates to certain new pyridin analogues of Formula ( I ) to processes for preparing such compounds, to their utility as P2Y12 inhibitors and as anti-trombotic agents etc, their use as medicaments in cardiovascular diseases as well as pharmaceutical compositions containing them.

  本发明涉及某些新的Formula（I）的吡啶类似物，以及制备这类化合物的方法，它们作为P2Y12抑制剂和抗血栓药物等的用途，它们在心血管疾病中作为药物的用途，以及含有它们的药物组合物。