6-(4-phenylpiperidin-1-yl)-3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazine | 1166816-05-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 6-(4-phenylpiperidin-1-yl)-3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazine
• 英文别名: 6-(4-Phenylpiperidin-1-yl)-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine
• CAS: 1166816-05-2
• 化学式: C₁₇H₁₆F₃N₅
• 分子量: 347.343
• InChiKey: BCYQYZUNNOWVSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  46.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  6-氯-3-(三氟甲基)[1,2,4]噻唑并[4,3-b]吡嗪 、 4-苯基哌啶 在 N,N-二异丙基乙胺 作用下， 以 乙醇 为溶剂， 以59%的产率得到6-(4-phenylpiperidin-1-yl)-3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazine
  参考文献：
  名称：

  Small-molecule androgen receptor downregulators as an approach to treatment of advanced prostate cancer

  摘要：

  Chemical starting points were investigated for downregulation of the androgen receptor as an approach to treatment of advanced prostate cancer. Although prototypic steroidal downregulators such as 6a designed for intramuscular administration showed insufficient cellular potency, a medicinal chemistry program derived from a novel androgen receptor ligand 8a led to 6-[4-(4-cyanobenzyl)piperazin-1-yl]3-(trifluoromethyl)[1,2,4] triazolo[4,3-b] pyridazine (10b), for which high plasma levels following oral administration in a preclinical model compensate for moderate cellular potency. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.122

文献信息

• BICYCLIC DERIVATIVES FOR USE IN THE TREATMENT OF ANDROGEN RECEPTOR ASSOCIATED CONDITIONS-155
  申请人：Bradbury Robert Hugh

  公开号：US20100016279A1

  公开（公告）日：2010-01-21

  The invention concerns bicyclic compounds of Formula I wherein the integers X 1 , X 2 , X 3 , Ring A, R 4 , R 5 and m are as defined in the description. The present invention also relates to processes for the preparation of such compounds, pharmaceutical compositions containing them and their use in the manufacture of a medicament for use in the prevention or treatment of androgen-receptor associated conditions.

  本发明涉及公式I的双环化合物，其中整数X1、X2、X3、环A、R4、R5和m如描述中所定义。本发明还涉及制备这种化合物的方法、包含它们的制药组合物以及它们在制造用于预防或治疗与雄激素受体相关疾病的药物中的应用。
• US8003649B2
  申请人：——

  公开号：US8003649B2

  公开（公告）日：2011-08-23
• Small-molecule androgen receptor downregulators as an approach to treatment of advanced prostate cancer
  作者：Robert H. Bradbury、Neil J. Hales、Alfred A. Rabow、Graeme E. Walker、David G. Acton、David M. Andrews、Peter Ballard、Nigel A.N. Brooks、Nicola Colclough、Alan Girdwood、Urs J. Hancox、Owen Jones、David Jude、Sarah A. Loddick、Andrew A. Mortlock

  DOI：10.1016/j.bmcl.2011.06.122

  日期：2011.9

  Chemical starting points were investigated for downregulation of the androgen receptor as an approach to treatment of advanced prostate cancer. Although prototypic steroidal downregulators such as 6a designed for intramuscular administration showed insufficient cellular potency, a medicinal chemistry program derived from a novel androgen receptor ligand 8a led to 6-[4-(4-cyanobenzyl)piperazin-1-yl]3-(trifluoromethyl)[1,2,4] triazolo[4,3-b] pyridazine (10b), for which high plasma levels following oral administration in a preclinical model compensate for moderate cellular potency. (C) 2011 Elsevier Ltd. All rights reserved.