(1R)-2-[(6-{4-[4-(cyclopentylsulfonyl)phenyl]butoxy}hexyl)amino]-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol | 686351-05-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: (1R)-2-[(6-{4-[4-(cyclopentylsulfonyl)phenyl]butoxy}hexyl)amino]-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol
• 英文别名: (1R)-2-[6-[4-(4-cyclopentylsulfonylphenyl)butoxy]hexylamino]-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol
• CAS: 686351-05-3
• 化学式: C₃₃H₄₉NO₆S
• 分子量: 587.821
• InChiKey: COFVEWMUNWIVGI-HKBQPEDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  41
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1R)-2-[(6-{4-[4-(cyclopentylsulfonyl)phenyl]butoxy}hexyl)amino]-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol 、 溶剂黄146 以 水 为溶剂， 生成 4-{(1R)-2-[(6-{4-[4-(cyclopentylsulfonyl)phenyl]butoxy}hexyl)amino]-1-hydroxyethyl}-2-(hydroxymethyl)phenol acetate
  参考文献：
  名称：

  Discovery of a Rapidly Metabolized, Long-Acting β₂ Adrenergic Receptor Agonist with a Short Onset Time Incorporating a Sulfone Group Suitable for Once-Daily Dosing

  摘要：

  A series of novel, potent, and selective human beta(2) adrenoceptor agonists incorporating a sulfone moiety on the terminal right-hand-side phenyl ring of (R)-salmeterol is presented. Sulfone 10b had salmeterol-like potency and selectivity profile, long duration of action on guinea pig trachea, and longer than salmeterol duration of action in vivo, suitable for once-daily dosing. It had lower than salmeterol oral absorption in rat, lower bioavailability in rat and dog, and a high turnover in human hepatocytes. It was metabolized in human hepatocytes by hydroxylation, oxidation, cleavage, and conjugation; most of the metabolites would be expected to have reduced or no beta(2) activity. The 4-biphenylsulfonic acid was identified as a crystalline, non-hygroscopic salt of 10b, suitable for inhaled delivery. Furthermore, it was free of any genetic toxicity issues and was considered as a backup to vilanterol.

  DOI：

  10.1021/jm401532g
• 作为产物：
  描述：

  (1R)-2-{[6-({4-[4-(cyclopentylsulfonyl)phenyl]but-3-ynyl}oxy)hexyl]amino}-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol 在 钯 silica 作用下， 以 乙酸乙酯 为溶剂， 反应 19.0h， 以to give the title compound (65 mg) LCMS RT=2.85 min的产率得到(1R)-2-[(6-{4-[4-(cyclopentylsulfonyl)phenyl]butoxy}hexyl)amino]-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol
  参考文献：
  名称：

  Phenethanolamine derivative for the treatment of respiratory diseases

  摘要：

  本发明涉及式(I)的新化合物，以及制造它们的过程，包含它们的药物组合物，以及它们在治疗中的应用，特别是在预防和治疗呼吸系统疾病方面的应用。

  公开号：

  US07442839B2

文献信息

• [EN] PHENETHANOLAMINE DERIVATIVE FOR THE TREATMENT OF RESPIRATORY DISEASES<br/>[FR] DERIVE DE PHENETHANOLAMINE UTILISE DANS LE TRAITEMENT DE MALADIES RESPIRATOIRES
  申请人：GLAXO GROUP LTD

  公开号：WO2004037773A1

  公开（公告）日：2004-05-06

  The present invention relates to novel compounds of formula (I), to a process for their manufacture, to pharmaceutical compositions containing them, and to their use in therapy, in particular their use in the prophylaxis and treatment of respiratory diseases.

  本发明涉及公式（I）的新化合物，以及其制备方法、含有它们的药物组合物，以及它们在治疗中的使用，特别是在预防和治疗呼吸道疾病中的使用。
• PHENETHANOLAMINE DERIVATIVE FOR THE TREATMENT OF RESPIRATORY DISEASES
  申请人：GLAXO GROUP LIMITED

  公开号：EP1556342B1

  公开（公告）日：2008-03-26
• US7442839B2
  申请人：——

  公开号：US7442839B2

  公开（公告）日：2008-10-28