ethyl 3-amino-5-benzyl-1H-pyrazole-4-carboxylate | 1292827-51-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 3-amino-5-benzyl-1H-pyrazole-4-carboxylate
• CAS: 1292827-51-0
• 化学式: C₁₃H₁₅N₃O₂
• 分子量: 245.281
• InChiKey: HDUINCBENWBHMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  81
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 3-amino-5-benzyl-1H-pyrazole-4-carboxylate 在 sodium tetrahydroborate 、 sodium hydride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 oil 为溶剂， 生成 ethyl 2-benzyl-7,7-dimethyl-5-phenyl-4,7-tetrahydropyrazolo [1,5-a]pyrimidine-3-carboxylate
  参考文献：
  名称：

  Novel and potent calcium-sensing receptor antagonists: Discovery of (5R)-N-[1-ethyl-1-(4-ethylphenyl)propyl]-2,7,7-trimethyl-5-phenyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxamide monotosylate (TAK-075) as an orally active bone anabolic agent

  摘要：

  The calcium-sensing receptor antagonist (CaSR) has been recognized as a promising target of anabolic agents for treating osteoporosis. In the course of developing a new drug candidate for osteoporosis, we found tetrahydropyrazolopyrimidine derivative 1 to be an orally active CaSR antagonist that stimulated transient PTH secretion in rats. However, compound 1 showed poor physical and chemical stability. In order to work out this compound's chemical stability and further understand its in vivo efficacy, we focused on modifying the 2-position of the tetrahydropyrazolopyrimidine. As a result of chemical modification, we discovered (5R)-N-[1-ethyl-1-(4-ethylphenyl)propyl]-2,7,7-trimethyl-5-phenyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxamide monotosylate 10m (TAK-075), which showed improved solubility, chemical stability, and in vivo efficacy. Furthermore, we describe that evaluating the active metabolite is important during repeated treatment with short-acting CaSR antagonists. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.02.001

文献信息

• BENZAMIDE DERIVATIVES AS OXYTOCIN AGONISTS AND VASOPRESSIN ANTAGONISTS
  申请人：Ferring B.V.

  公开号：EP1592693A1

  公开（公告）日：2005-11-09
• [EN] BENZAMIDE DERIVATIVES AS OXYTOCIN AGONISTS AND VASOPRESSIN ANTAGONISTS<br/>[FR] DERIVES DE BENZAMIDE EN TANT QU'AGONISTES D'OXYTOCINE ET ANTAGONISTES DE VASOPRESSINE
  申请人：FERRING BV

  公开号：WO2004072083A1

  公开（公告）日：2004-08-26

  Novel compounds according to general formula 1, wherein Gl is NR5R6 or a fused polycyclic group that are specific OT receptor agonists and/or Vla receptor antagonists. Pharmaceutical compositions comprising such compounds are useful in the treatment of, inter alia, primary dysmenorrhoea.