4-formyl-2-(morpholinomethyl)phenyl trifluoromethanesulfonate | 1197291-78-3

• 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: 4-formyl-2-(morpholinomethyl)phenyl trifluoromethanesulfonate
• 英文别名: 4-Formyl-2-(morpholinomethyl)phenyl trifluoromethanesulfonate；[4-formyl-2-(morpholin-4-ylmethyl)phenyl] trifluoromethanesulfonate
• CAS: 1197291-78-3
• 化学式: C₁₃H₁₄F₃NO₅S
• 分子量: 353.319
• InChiKey: QWNORQNPMCZMKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  81.3
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-formyl-2-(morpholinomethyl)phenyl trifluoromethanesulfonate 在 2-双环己基膦-2',6'-二甲氧基联苯 、 palladium diacetate 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 22.25h， 生成 tert-butyl (1s,4s)-4-(2-(4'-(((3S,5R)-3,5-dimethylpiperazin-1-yl)methyl)-2'-(morpholinomethyl)biphenyl-3-yloxy)-5-fluoronicotinamido)cyclohexylcarbamate
  参考文献：
  名称：

  Efficacious Inhaled PDE4 Inhibitors with Low Emetic Potential and Long Duration of Action for the Treatment of COPD

  摘要：

  Oral phosphodiesterase 4 (PDE4) inhibitors, such as cilomilast and roflumilast, have been shown to be efficacious against chronic obstructive pulmonary disease (COPD). However, these drugs have been hampered by mechanism-related side effects such as nausea and emesis at high doses. Compounds administered by inhalation are delivered directly to the site of action and may improve the therapeutic index required to overcome side effects. This paper describes systematic and rational lead optimization to deliver highly potent, long-acting, and efficacious preclinical inhaled PDE4 inhibitors with low emetic potential.

  DOI：

  10.1021/jm5001216
• 作为产物：
  描述：

  对羟基苯甲醛 在 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 16.0h， 生成 4-formyl-2-(morpholinomethyl)phenyl trifluoromethanesulfonate
  参考文献：
  名称：

  Efficacious Inhaled PDE4 Inhibitors with Low Emetic Potential and Long Duration of Action for the Treatment of COPD

  摘要：

  Oral phosphodiesterase 4 (PDE4) inhibitors, such as cilomilast and roflumilast, have been shown to be efficacious against chronic obstructive pulmonary disease (COPD). However, these drugs have been hampered by mechanism-related side effects such as nausea and emesis at high doses. Compounds administered by inhalation are delivered directly to the site of action and may improve the therapeutic index required to overcome side effects. This paper describes systematic and rational lead optimization to deliver highly potent, long-acting, and efficacious preclinical inhaled PDE4 inhibitors with low emetic potential.

  DOI：

  10.1021/jm5001216

文献信息

• [EN] PHENOXYPYRIDINYLAMIDE DERIVATIVES AND THEIR USE IN THE TREATMENT OF PDE4 MEDIATED DISEASE STATES<br/>[FR] DÉRIVÉS DE PHÉNOXYPYRIDINYLAMIDE ET LEUR UTILISATION DANS LE TRAITEMENT D'ÉTATS PATHOLOGIQUES INDUITS PAR LA PHOSPHODIÉSTERASE 4 (PDE4)
  申请人：ASTRAZENECA AB

  公开号：WO2009144494A1

  公开（公告）日：2009-12-03

  The present invention provides a compound of a formula (I), wherein the variables are defined herein; to a process for preparing such a compound; and to the use of such a compound in the treatment of a PDE4 mediated disease state.

  本发明提供了一种化合物的公式(I)，其中变量在此定义；以及制备这种化合物的方法；以及在治疗PDE4介导的疾病状态中使用这种化合物。
• Chemical Compounds 293
  申请人：Andrews Glen

  公开号：US20100041638A1

  公开（公告）日：2010-02-18

  The present invention provides a compound of a formula (I): wherein the variables are defined herein; to a process for preparing such a compound; and to the use of such a compound in the treatment of a PDE4 mediated disease state.

  本发明提供了一个式子（I）的化合物： 其中，变量在此定义；以及制备这种化合物的过程；以及在治疗PDE4介导的疾病状态中使用这种化合物的用途。
• Phenoxypyridinylamide compounds
  申请人：AstraZeneca AB

  公开号：US08273774B2

  公开（公告）日：2012-09-25

  The present invention provides a compound of a formula (I): wherein the variables are defined herein; to a process for preparing such a compound; and to the use of such a compound in the treatment of a PDE4 mediated disease state.

  本发明提供了一个化合物的公式（I）：其中变量在此定义；以及制备这样的化合物的过程；以及使用这样的化合物治疗PDE4介导的疾病状态。
• Phenoxypyridinylamide derivatives and their use in the treatment of PDE4 mediated disease states
  申请人：AstraZeneca AB (Publ)

  公开号：EP2778156A1

  公开（公告）日：2014-09-17

  The present invention provides a compound of a formula (I): wherein the variables are defined herein; to a process for preparing such a compound; and to the use of such a compound in the treatment of a PDE4 mediated disease state.

  本发明提供了一种式 (I) 的化合物： 其中的变量在本文中定义；提供了制备这种化合物的工艺；并提供了这种化合物在治疗 PDE4 介导的疾病状态中的用途。
• PHENOXYPYRIDINYLAMIDE DERIVATIVES AND THEIR USE IN THE TREATMENT OF PDE4 MEDIATED DISEASE STATES
  申请人：AstraZeneca AB

  公开号：EP2297106A1

  公开（公告）日：2011-03-23