Tert-butyl 2-[[4-(trifluoromethoxy)phenyl]carbamoyl]-2,9-diazaspiro[5.5]undecane-9-carboxylate | 1448754-02-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 英文名称: Tert-butyl 2-[[4-(trifluoromethoxy)phenyl]carbamoyl]-2,9-diazaspiro[5.5]undecane-9-carboxylate
• 英文别名: tert-butyl 2-[[4-(trifluoromethoxy)phenyl]carbamoyl]-2,9-diazaspiro[5.5]undecane-9-carboxylate
• CAS: 1448754-02-6
• 化学式: C₂₂H₃₀F₃N₃O₄
• 分子量: 457.493
• InChiKey: ULWRFNVIURYICJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  71.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Tert-butyl 2-[[4-(trifluoromethoxy)phenyl]carbamoyl]-2,9-diazaspiro[5.5]undecane-9-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 N-[4-(trifluoromethoxy)phenyl]-2,9-diazaspiro[5.5]undecane-2-carboxamide
  参考文献：
  名称：

  Discovery of 1-oxa-4,9-diazaspiro[5.5]undecane-based trisubstituted urea derivatives as highly potent soluble epoxide hydrolase inhibitors and orally active drug candidates for treating of chronic kidney diseases

  摘要：

  We identified 1-oxa-4,9-diazaspiro[5.5]undecane-based trisubstituted ureas as highly potent soluble epoxide hydrolase (sEH) inhibitors and orally active agents for treating chronic kidney diseases. Compound 19 exhibited excellent sEH inhibitory activity and bioavailability. When administered orally at 30 mg/kg, 19 lowered serum creatinine in a rat model of anti-glomerular basement membrane glomerulonephritis but 2,8-diazaspiro[4.5]decane-based trisubstituted ureas did not. These results suggest that 19 is an orally active drug candidate for treating chronic kidney diseases. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.020
• 作为产物：
  描述：

  N-Boc-4-哌啶甲醇 在 盐酸 、 palladium on activated charcoal 、 氢气 、 苄基三甲基氢氧化铵 、 戴斯-马丁氧化剂 、 三乙胺 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 氯仿 、 水 为溶剂， 生成 Tert-butyl 2-[[4-(trifluoromethoxy)phenyl]carbamoyl]-2,9-diazaspiro[5.5]undecane-9-carboxylate
  参考文献：
  名称：

  Discovery of 1-oxa-4,9-diazaspiro[5.5]undecane-based trisubstituted urea derivatives as highly potent soluble epoxide hydrolase inhibitors and orally active drug candidates for treating of chronic kidney diseases

  摘要：

  We identified 1-oxa-4,9-diazaspiro[5.5]undecane-based trisubstituted ureas as highly potent soluble epoxide hydrolase (sEH) inhibitors and orally active agents for treating chronic kidney diseases. Compound 19 exhibited excellent sEH inhibitory activity and bioavailability. When administered orally at 30 mg/kg, 19 lowered serum creatinine in a rat model of anti-glomerular basement membrane glomerulonephritis but 2,8-diazaspiro[4.5]decane-based trisubstituted ureas did not. These results suggest that 19 is an orally active drug candidate for treating chronic kidney diseases. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.020

文献信息

• [EN] DIAZASPIRO UREA DERIVATIVE AND PHARMACEUTICAL USE THEREOF<br/>[FR] DÉRIVÉ DE DIAZASPIRO-URÉE ET SON UTILISATION PHARMACEUTIQUE
  申请人：TORAY INDUSTRIES

  公开号：WO2013115294A1

  公开（公告）日：2013-08-08

  本発明は、ｓＥＨ阻害活性に基づき高血圧に対して治療効果を発揮する医薬を提供することを目的としている。本発明は、下記に代表されるジアザスピロウレア誘導体又はその薬理学的に許容される塩を提供する。
• Discovery of 1-oxa-4,9-diazaspiro[5.5]undecane-based trisubstituted urea derivatives as highly potent soluble epoxide hydrolase inhibitors and orally active drug candidates for treating of chronic kidney diseases
  作者：Yuko Kato、Nobuhiro Fuchi、Yutaka Nishimura、Ayano Watanabe、Mai Yagi、Yasuhito Nakadera、Eriko Higashi、Masateru Yamada、Takumi Aoki、Hideo Kigoshi

  DOI：10.1016/j.bmcl.2013.12.020

  日期：2014.1

  We identified 1-oxa-4,9-diazaspiro[5.5]undecane-based trisubstituted ureas as highly potent soluble epoxide hydrolase (sEH) inhibitors and orally active agents for treating chronic kidney diseases. Compound 19 exhibited excellent sEH inhibitory activity and bioavailability. When administered orally at 30 mg/kg, 19 lowered serum creatinine in a rat model of anti-glomerular basement membrane glomerulonephritis but 2,8-diazaspiro[4.5]decane-based trisubstituted ureas did not. These results suggest that 19 is an orally active drug candidate for treating chronic kidney diseases. (C) 2013 Elsevier Ltd. All rights reserved.