N-[5-((1R)-2-{benzyl[6-(but-3-ynyloxy)hexyl]amino}-1-hydroxyethyl)-2-(benzyloxy)phenyl]formamide | 463934-72-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[5-((1R)-2-{benzyl[6-(but-3-ynyloxy)hexyl]amino}-1-hydroxyethyl)-2-(benzyloxy)phenyl]formamide
• 英文别名: 5-((1R)-2-{benzyl[6-(but-3-ynyloxy)hexyl]amino}-1-hydroxyethyl)-2-(benzyloxy)phenylformamide；N-[5-[(1R)-2-[benzyl(6-but-3-ynoxyhexyl)amino]-1-hydroxyethyl]-2-phenylmethoxyphenyl]formamide
• CAS: 463934-72-7
• 化学式: C₃₃H₄₀N₂O₄
• 分子量: 528.692
• InChiKey: AAOABHUBJHOCRR-YTTGMZPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  39
• 可旋转键数：
  18
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  71
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[5-((1R)-2-{benzyl[6-(but-3-ynyloxy)hexyl]amino}-1-hydroxyethyl)-2-(benzyloxy)phenyl]formamide 、 1-(3-iodophenyl)urea 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 三乙胺 作用下， 以 乙腈 为溶剂， 反应 4.5h， 生成 N-[3-(4-{[6-(benzyl{(2R)-2-[4-(benzyloxy)-3-(formylamino)phenyl]-2-hydroxyethyl}amino)hexyl]oxy}but-1-ynyl)phenyl]urea
  参考文献：
  名称：

  [EN] PHENYLETHANOLAMINE DERIVATIVES FOR THE TREATMENT OF RESPIRATORY DISEASES
  [FR] DERIVES DE PHENYLETHANOLAMINE POUR LE TRAITEMENT DE MALADIES RESPIRATOIRES

  摘要：

  本发明涉及公式（I）的新化合物，以及制备它们的方法，含有它们的药物组合物，以及它们在治疗中的应用，特别是在预防和治疗呼吸道疾病中的应用。

  公开号：

  WO2004039766A1
• 作为产物：
  描述：

  benzyloxy-5-[(2R)-oxiran-2-yl]phenylformamide 、 N-benzyl-6-(but-3-ynyloxy)hexan-1-amine 在 cyclohexane, ethyl acetate 作用下， 反应 2.0h， 以to give the title compound (13.47 g)的产率得到N-[5-((1R)-2-{benzyl[6-(but-3-ynyloxy)hexyl]amino}-1-hydroxyethyl)-2-(benzyloxy)phenyl]formamide
  参考文献：
  名称：

  Formailide derivatives as beta2-adrenoreceptor agonists

  摘要：

  本发明涉及一种新的化合物（I）的公式，其制造过程，包含它们的制药组合物以及它们在治疗中的用途，特别是在预防和治疗呼吸系统疾病中的应用。

  公开号：

  US20040157830A1

文献信息

• [EN] PHENETHANOLAMINE DERIVATIVES FOR THE TREATMENT OF RESPIRATORY DISEASES<br/>[FR] DERIVES DE PHENETHANOLAMINE PERMETTANT DE TRAITER DES MALADIES DES VOIES RESPIRATOIRES
  申请人：GLAXO GROUP LTD

  公开号：WO2004039762A1

  公开（公告）日：2004-05-13

  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.

  本发明涉及式（I）的新化合物，以及制备它们的方法，含有它们的药物组合物，以及它们在治疗中的应用，特别是在预防和治疗呼吸道疾病中的应用。
• Synthesis and Structure−Activity Relationships of Long-acting β₂ Adrenergic Receptor Agonists Incorporating Arylsulfonamide Groups
  作者：Panayiotis A. Procopiou、Victoria J. Barrett、Nicola J. Bevan、Keith Biggadike、Peter R. Butchers、Diane M. Coe、Richard Conroy、Dean D. Edney、Rita N. Field、Alison J. Ford、Stephen B. Guntrip、Brian E. Looker、Iain M. McLay、Michael J. Monteith、Valerie S. Morrison、Peter J. Mutch、Stephen A. Richards、Rosemary Sasse、Claire E. Smith

  DOI：10.1021/jm801016j

  日期：2009.4.23

  A series of saligenin alkoxyalkylphenylsulfonamide beta(2) adrenoceptor agonists were prepared by reacting a protected saligenin oxazolidinone with alkynyloxyalkyl bromides, followed by Sonogashira reaction, hydrogenation, and deprotection. The meta-substituted primary sulfonamide was more potent than the para and the ortho-analogues. Primary sulfonamides were more potent than the secondary and tertiary analogues. The onset and duration of action in vitro of selected compounds was assessed on isolated superfused guinea pig trachea. Sulfonamide 29b had the best profile of potency, selectivity, onset, and duration of action on both guinea pig trachea and human bronchus. Furthermore, 29b was found to have low oral bioavailability in rat and dog and also to have long duration of action in an in vivo model of bronchodilation. Crystalline salts of 29b were identified that had suitable properties for inhaled administration. A proposed binding mode for 29b to the beta(2)-receptor is presented.
• FORMANILIDE DERIVATIVES AS BETA2-ADRENORECEPTOR AGONISTS
  申请人：GLAXO GROUP LIMITED

  公开号：EP1370521A1

  公开（公告）日：2003-12-17
• US7045658B2
  申请人：——

  公开号：US7045658B2

  公开（公告）日：2006-05-16
• [EN] FORMAILIDE DERIVATIVES AS BETA2-ADRENORECEPTOR AGONISTS<br/>[FR] DERIVES FORMANILIDES UTILISES EN TANT QU'AGONISTES DE L'ADRENORECEPTEUR BETA2
  申请人：GLAXO GROUP LTD

  公开号：WO2002076933A1

  公开（公告）日：2002-10-03

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