8-butoxy-5-[2-[(5,6-diethyl-2,3-dihydro-1H-inden-2-yl)amino]-1-hydroxyethyl]-1H-quinolin-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 8-butoxy-5-[2-[(5,6-diethyl-2,3-dihydro-1H-inden-2-yl)amino]-1-hydroxyethyl]-1H-quinolin-2-one
• 化学式: C₂₈H₃₆N₂O₃
• 分子量: 448.6
• InChiKey: WZCDUFSPDRMAJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  70.6
• 氢给体数：
  3
• 氢受体数：
  4

文献信息

• [EN] A METHOD FOR THE PREPARATION OF 5-[(R)-2-(5,6-DIETHYL-INDAN-2-YLAMINO)-L-HYDROXYETHYL]- 8-HYDROXY-(1H)-QUINOLIN-2-ONE (INDACATEROL)<br/>[FR] PROCÉDÉ DE PRÉPARATION DE LA 5-[(R)-2-(5,6-DIÉTHYL-INDAN-2-YLAMINO)-1-HYDROXYÉTHYL]-8-HYDROXY-(1H)-QUINOLÉIN-2-ONE (INDACATÉROL)
  申请人：ZENTIVA KS

  公开号：WO2014139485A1

  公开（公告）日：2014-09-18

  The invention relates to a new method of synthesis of 5-[(R)-2-(5,6-diethyl-indan-2-ylamino)- 1-hydroxyethyl]-8-hydroxy-(1H)-quinolin-2-one of formula (R)-2, known under the generic name indacaterol, which is used for the treatment of chronic obstructive pulmonary disease (COPD). The method comprises preparation of the racemic intermediate 5-[2-(5,6-diethyl-indan-2-ylamino)-1-hydroxyethyl]-8-benzyloxy-(1H)-quinolin-2-one of formula 1, which is further, in an arbitrary order, chirally resolved and debenzylated, and subsequently indacaterol of formula (R)-2 is isolated.

  该发明涉及一种新的合成方法，用于合成化学式为5-[(R)-2-(5,6-二乙基茚-2-基氨基)-1-羟乙基]-8-羟基-(1H)-喹啉-2-酮的化合物（R)-2，通用名称为吲托特罗，用于治疗慢性阻塞性肺病（COPD）。该方法包括制备外消旋中间体5-[2-(5,6-二乙基茚-2-基氨基)-1-羟乙基]-8-苄氧基-(1H)-喹啉-2-酮的化合物1，然后，以任意顺序进行立体分离和脱苄基化，并最终分离出吲托特罗的化学式（R)-2。
• INDACATEROL FREE BASE IN SOLID FORM
  申请人：Crystal Pharma, S.A.U.

  公开号：EP3138837A1

  公开（公告）日：2017-03-08

  The present invention relates to the Indacaterol free base in solid form. The Indacataterol free base may be in a crystalline form or in an amorphous form. The present invention also discloses an improved preparation of the Idacaterol maleate salt using the isolated Indacaterol free base in solid form as an intermediate. Indacataterol (5-[(R)-2-(5,6-diethyl-indan-2-ylamino)-1-hydroxyethyl]-8-hydroxy-(1H)-quinolin-2-one) is a beta-selective adrenoceptor agonists with a potent bronchodilating activity. Indacaterol is especially useful for the treatment of asthma and chronic obstructive pulmonary disease (COPD) and is sold commercially as the maleate salt.

  本发明涉及固体形式的茚达特罗游离基。茚达特罗游离碱可以是结晶形式或无定形形式。 本发明还公开了一种以分离的固体形式的茚达特罗游离碱为中间体制备马来酸茚达特罗盐的改进方法。 茚达特罗（5-[(R)-2-(5,6-二乙基-茚满-2-基氨基)-1-羟乙基]-8-羟基-(1H)-喹啉-2-酮）是一种β选择性肾上腺素受体激动剂，具有强效的支气管扩张活性。茚达特罗尤其适用于治疗哮喘和慢性阻塞性肺病（COPD），以马来酸盐的形式进行商业销售。