3-[4-(2-methoxyethoxy)piperidine-4-carboxamido]phenyl N,N-dimethylcarbamate hydrochloride | 1192189-63-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-[4-(2-methoxyethoxy)piperidine-4-carboxamido]phenyl N,N-dimethylcarbamate hydrochloride
• 英文别名: 3-(4-((2-methoxyethoxy)methyl)piperidine-4-carboxamido)phenyl dimethylcarbamate hydrochloride
• CAS: 1192189-63-1
• 化学式: C₁₉H₂₉N₃O₅*ClH
• 分子量: 415.917
• InChiKey: BIDCBCVHMCRLMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.14
• 重原子数：
  28.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  89.13
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-[4-(2-methoxyethoxy)piperidine-4-carboxamido]phenyl N,N-dimethylcarbamate hydrochloride 、 4-氯-5-甲基-7H-吡咯并[2,3-d]嘧啶 在 N,N-二异丙基乙胺 作用下， 以 异丙醇 为溶剂， 反应 18.0h， 以61%的产率得到3-{4-[(2-methoxyethoxy)methyl]-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamido}phenyl N,N-dimethylcarbamate
  参考文献：
  名称：

  LIMK2 INHIBITORS, COMPOSITIONS COMPRISING THEM, AND METHODS OF THEIR USE

  摘要：

  LIM激酶2的抑制剂已被披露，以及包含它们的药物组合物和它们的使用方法。特定化合物的化学式如下：

  公开号：

  US20090264450A1
• 作为产物：
  描述：

  1-(tert-butoxycarbonyl)-4-(2-methoxyethoxy)piperidine-4-carboxylic acid 在 吡啶 、 盐酸 、 甲醇 、 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 3-[4-(2-methoxyethoxy)piperidine-4-carboxamido]phenyl N,N-dimethylcarbamate hydrochloride
  参考文献：
  名称：

  Discovery and Development of LX7101, a Dual LIM-Kinase and ROCK Inhibitor for the Treatment of Glaucoma

  摘要：

  The structure of LX7101, a dual LIM-kinase and ROCK inhibitor for the treatment of ocular hypertension and associated glaucoma, is disclosed. Previously reported LIM kinase inhibitors suffered from poor aqueous stability due to solvolysis of the central urea. Replacement of the urea with a hindered amide resulted in aqueous stable compounds, and addition of solubilizing groups resulted in a set of compounds with good properties for topical dosing in the eye and good efficacy in a mouse model of ocular hypertension. LX7101 was selected as a clinical candidate from this group based on superior efficacy in lowering intraocular pressure and a good safety profile. LX7101 completed IND enabling studies and was tested in a Phase 1 clinical trial in glaucoma patients, where it showed efficacy in lowering intraocular pressure.

  DOI：

  10.1021/ml500367g