(R)-2-{[ethyl-(3-phenoxy-phenyl)-amino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester | 1105706-95-3

• 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: (R)-2-{[ethyl-(3-phenoxy-phenyl)-amino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (2R)-2-[(N-ethyl-3-phenoxyanilino)methyl]pyrrolidine-1-carboxylate
• CAS: 1105706-95-3
• 化学式: C₂₄H₃₂N₂O₃
• 分子量: 396.53
• InChiKey: XFGWKIKIJNINMQ-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  42
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-2-{[ethyl-(3-phenoxy-phenyl)-amino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester 在 三氟乙酸 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 3.0h， 以36%的产率得到ethyl-(3-phenoxy-phenyl)-(R)-1pyrrolidin-2-ylmethyl-amine
  参考文献：
  名称：

  2-AZETIDINEMETHANEAMINES AND 2-PYRROLIDINEMETHANEAMINES AS TAAR-LIGANDS

  摘要：

  本发明涉及式I的化合物，其中R1、R2、R3、Ar、n和o如本文所定义，并且它们的药学上可接受的活性盐。式I的化合物具有良好的亲和力，特别是对TAAR1，可用于治疗抑郁症、焦虑症、双相情感障碍、注意力缺陷多动障碍（ADHD）、与压力相关的疾病、精神疾病，如精神分裂症、神经疾病，如帕金森病、神经退行性疾病，如阿尔茨海默病、癫痫、偏头痛、高血压、物质滥用以及代谢性疾病，如进食障碍、糖尿病、糖尿病并发症、肥胖症、血脂异常、能量消耗和吸收障碍、体温稳态障碍、睡眠和昼夜节律障碍以及心血管疾病的治疗。

  公开号：

  US20090029962A1
• 作为产物：
  描述：

  tert-butyl (R)-2-(((3-phenoxyphenyl)amino)methyl)pyrrolidine-1-carboxylate 、 乙醛 在 zinc(II) chloride sodium cyanoborohydride 、 ammonium acetate 、 水 作用下， 以 甲醇 为溶剂， 以67%的产率得到(R)-2-{[ethyl-(3-phenoxy-phenyl)-amino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  2-AZETIDINEMETHANEAMINES AND 2-PYRROLIDINEMETHANEAMINES AS TAAR-LIGANDS

  摘要：

  本发明涉及式I的化合物，其中R1、R2、R3、Ar、n和o如本文所定义，并且它们的药学上可接受的活性盐。式I的化合物具有良好的亲和力，特别是对TAAR1，可用于治疗抑郁症、焦虑症、双相情感障碍、注意力缺陷多动障碍（ADHD）、与压力相关的疾病、精神疾病，如精神分裂症、神经疾病，如帕金森病、神经退行性疾病，如阿尔茨海默病、癫痫、偏头痛、高血压、物质滥用以及代谢性疾病，如进食障碍、糖尿病、糖尿病并发症、肥胖症、血脂异常、能量消耗和吸收障碍、体温稳态障碍、睡眠和昼夜节律障碍以及心血管疾病的治疗。

  公开号：

  US20090029962A1

文献信息

• 2-azetidinemethaneamines and 2-pyrrolidinemethaneamines as TAAR-ligands
  申请人：Galley Guido

  公开号：US08389507B2

  公开（公告）日：2013-03-05

  The present invention relates to compounds of formula I wherein R1, R2, R3, Ar, n and o are as defined herein and to their pharmaceutically acceptable active salts. Compounds of formula I have a good affinity to the trace amine associated receptors (TAARs), especially for TAAR1 and are useful for the treatment of depression, anxiety disorders, bipolar disorder, attention deficit hyperactivity disorder (ADHD), stress-related disorders, psychotic disorders such as schizophrenia, neurological diseases such as Parkinson's disease, neurodegenerative disorders such as Alzheimer's disease, epilepsy, migraine, hypertension, substance abuse and metabolic disorders such as eating disorders, diabetes, diabetic complications, obesity, dyslipidemia, disorders of energy consumption and assimilation, disorders and malfunction of body temperature homeostasis, disorders of sleep and circadian rhythm, and cardiovascular disorders.

  本发明涉及式I的化合物，其中R1、R2、R3、Ar、n和o如本文所定义，并且它们的药学上可接受的活性盐。式I的化合物具有良好的亲和力与微量胺相关受体(TAARs)结合，特别是TAAR1，适用于治疗抑郁症、焦虑症、躁郁症、注意力缺陷多动障碍(ADHD)、与压力相关的疾病、精神疾病如精神分裂症、神经疾病如帕金森病、神经退行性疾病如阿尔茨海默病、癫痫、偏头痛、高血压、物质滥用和代谢疾病如饮食失调、糖尿病、糖尿病并发症、肥胖症、脂质代谢异常、能量消耗和吸收障碍、体温稳态障碍和失调、睡眠和昼夜节律障碍以及心血管疾病。
• US8389507B2
  申请人：——

  公开号：US8389507B2

  公开（公告）日：2013-03-05
• [EN] 2-AZETIDINEMETHANEAMINES AND 2-PYRROLIDINEMETHANEAMINES AS TAAR-LIGANDS<br/>[FR] 2-AZÉTIDINEMÉTHANEAMINES ET 2-PYRROLIDINEMÉTHANEAMINES COMME LIGANDS DE TAAR
  申请人：HOFFMANN LA ROCHE

  公开号：WO2009016048A1

  公开（公告）日：2009-02-05

  The present invention relates to compounds of formula (I) wherein R1 is hydrogen, lower alkyl or benzyl which may be optionally substituted by halogen or lower alkoxy; R2 is hydrogen, halogen or OR, wherein R is lower alkyl, aryl or lower alkyl substituted by halogen; R3 is hydrogen or fluorine; Ar is phenyl; n is 0 or 1; o is 0, 1 or 2; and to their pharmaceutically active salts. It has been found that the compounds of formula I have a good affinity to the trace amine associated receptors (TAARs), especially for TAAR1. The compounds may be used for the treatment of depression, anxiety disorders, bipolar disorder, attention deficit hyperactivity disorder (ADHD), stress-related disorders, psychotic disorders such as schizophrenia, neurological diseases such as Parkinson's disease, neurodegenerative disorders such as Alzheimer's disease, epilepsy, migraine, hypertension, substance abuse and metabolic disorders such as eating disorders, diabetes, diabetic complications, obesity, dyslipidemia, disorders of energy consumption and assimilation, disorders and malfunction of body temperature homeostasis, disorders of sleep and circadian rhythm, and cardiovascular disorders.