(S)-fadrozole | 102676-86-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: (S)-fadrozole
• 英文别名: S-fadrazole；(-)-Fadrozole；4-[(5S)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl]benzonitrile
• CAS: 102676-86-8
• 化学式: C₁₄H₁₃N₃
• 分子量: 223.277
• InChiKey: CLPFFLWZZBQMAO-AWEZNQCLSA-N

物化性质

• 沸点：
  481.7±38.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  41.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  法倔唑 生成 (S)-fadrozole
  参考文献：
  名称：

  芳香酶抑制剂：唑类化合物的合成，生物学活性和结合方式。

  摘要：

  分离了有效的芳香酶法德罗唑盐酸盐3的非甾体抑制剂的对映体，并通过X射线晶体学测定了其绝对构型。根据活性对映异构体4和迄今为止报道的最有效的类固醇抑制剂之一（19R）-10-thiiranylestr-4-ene-3,17-dione，7的分子模型比较，该模型描述了相对提出了芳香酶的吡咯型和甾族抑制剂在酶活性位点的结合模式。建议最活跃的唑类抑制剂中存在的氰基苯基部分模拟芳香酶aserost-4-ene-3,17-dione，1的天然底物的类固醇骨架。

  DOI：

  10.1021/jm00062a012

文献信息

• Aldosterone synthase inhibitor
  申请人：DAMIAN PHARMA AG

  公开号：US10822332B2

  公开（公告）日：2020-11-03

  The present invention relates to a compound selected from (R)-(+)-5-(p-cyanophenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine and a pharmaceutically acceptable salt thereof, and in particular to the phosphate salt of (R)-(+)-5-(p-cyanophenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine, both having preferably an enantiomeric excess of the (R) form higher than or equal to 97%. Furthermore, the present invention relates to pharmaceutical compositions comprising the same, their use as a medicament and in methods of treatment of diseases and disorders in humans including women of child bearing potential and pediatric patients in which aldosterone over-exposure contributes to the deleterious effects of said diseases or disorders, as well as processes for preparing said inventive compounds.

  本发明涉及一种选自(R)-(+)-5-(对氰基苯基)-5,6,7,8-四氢咪唑并[1,5-a]吡啶的化合物及其药学上可接受的盐、特别是(R)-(+)-5-(对氰基苯基)-5,6,7,8-四氢咪唑并[1,5-a]吡啶的磷酸酯盐，两者的(R)形式对映体过量最好都大于或等于 97%。此外，本发明还涉及包含上述化合物的药物组合物、其作为药物的用途、治疗人类（包括具有生育能力的妇女和儿科患者）疾病和失调的方法（其中醛固酮过度暴露会导致上述疾病或失调的有害影响）以及制备上述发明化合物的工艺。
• R-FADROZOLE FOR USE IN THE TREATMENT OF ALDOSTONERISM
  申请人：Damian Pharma AG

  公开号：EP3787623A1

  公开（公告）日：2021-03-10
• ALDOSTERONE SYNTHASE INHIBITOR
  申请人：DAMIAN PHARMA AG

  公开号：US20190292180A1

  公开（公告）日：2019-09-26

  The present invention relates to a compound selected from (R)-(+)-5-(p-cyanophenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine and a pharmaceutically acceptable salt thereof, and in particular to the phosphate salt of (R)-(+)-5-(p-cyanophenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine, both having preferably an enantiomeric excess of the (R) form higher than or equal to 97%. Furthermore, the present invention relates to pharmaceutical compositions comprising the same, their use as a medicament and in methods of treatment of diseases and disorders in humans including women of child bearing potential and pediatric patients in which aldosterone over-exposure contributes to the deleterious effects of said diseases or disorders, as well as processes for preparing said inventive compounds.
• Aromatase inhibitors: synthesis, biological activity, and binding mode of azole-type compounds
  作者：P. Furet、C. Batzl、A. Bhatnagar、E. Francotte、G. Rihs、M. Lang

  DOI：10.1021/jm00062a012

  日期：1993.5

  binding modes of the azole-type and steroidal inhibitors of aromatase at the active site of the enzyme is proposed. It is suggested that the cyanophenyl moiety present in the most active azole inhibitors partially mimics the steroid backbone of the natural substrate for aromatase, androst-4-ene-3,17-dione, 1. The synthesis and biological testing of novel analogues of 3 used to define the accessible

  分离了有效的芳香酶法德罗唑盐酸盐3的非甾体抑制剂的对映体，并通过X射线晶体学测定了其绝对构型。根据活性对映异构体4和迄今为止报道的最有效的类固醇抑制剂之一（19R）-10-thiiranylestr-4-ene-3,17-dione，7的分子模型比较，该模型描述了相对提出了芳香酶的吡咯型和甾族抑制剂在酶活性位点的结合模式。建议最活跃的唑类抑制剂中存在的氰基苯基部分模拟芳香酶aserost-4-ene-3,17-dione，1的天然底物的类固醇骨架。