rac-(4,5-dihydro-3H-imidazol-4-ylmethyl)-ethyl-phenyl-amine | 1096690-02-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: rac-(4,5-dihydro-3H-imidazol-4-ylmethyl)-ethyl-phenyl-amine
• 英文别名: N-(4,5-dihydro-1H-imidazol-5-ylmethyl)-N-ethylaniline
• CAS: 1096690-02-6
• 化学式: C₁₂H₁₇N₃
• 分子量: 203.287
• InChiKey: NHXCDFXMZSNMKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  27.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  rac-N1-ethyl-N1-phenyl-propane-1,2,3-triamine 、 醋酸甲脒 在 水 、 二氯甲烷 、 magnesium sulfate 、 NH2 、 甲醇乙酸乙酯 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以to yield an off-white amorphous solid (0.042 g, 21%)的产率得到rac-(4,5-dihydro-3H-imidazol-4-ylmethyl)-ethyl-phenyl-amine
  参考文献：
  名称：

  4-imidazolines

  摘要：

  本发明涉及式I的化合物，其中R1、R2、X、Y和Ar的定义如下，并且涉及它们的药物活性盐，但排除了外消旋化合物4-苄基-4,5-二氢-1H-咪唑或其互变异构体（CAS 131548-83-9）。式I的化合物具有良好的亲和力，特别是对TAAR1的痕量胺相关受体（TAARs），并可用于治疗抑郁症、焦虑症、双相情感障碍、注意力缺陷多动障碍（ADHD）、与压力相关的障碍、精神障碍如精神分裂症、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、物质滥用和代谢性疾病如进食障碍、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、体温稳态障碍和功能障碍、睡眠和昼夜节律障碍以及心血管疾病。

  公开号：

  US07812047B2

文献信息

• 4-IMIDAZOLINES
  申请人：Galley Guido

  公开号：US20090012138A1

  公开（公告）日：2009-01-08

  The present invention relates to compounds of formula wherein R 1 , R 2 , X, Y and Ar are as defined herein and to their pharmaceutically active salts, with the exclusion of the racemic compound 4-benzyl-4,5-dihydro-1H-imidazole or its tautomer (CAS 131548-83-9). 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，X，Y和Ar如此定义，并且它们的药物活性盐，但排除外消旋化合物4-苄基-4,5-二氢-1H-咪唑或其互变异构体（CAS 131548-83-9）。式I的化合物具有良好的迹胺相关受体（TAARs）亲和力，尤其是对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），与压力相关的障碍，精神障碍，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，物质滥用和代谢性疾病，如进食障碍，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，体温稳态障碍和功能障碍，睡眠和昼夜节律障碍，以及心血管疾病。
• [EN] 4-IMIDAZOLINES AND THEIR USE AS ANTIDEPRESSANTS<br/>[FR] 4-IMIDAZOLINES ET LEUR UTILISATION COMME ANTIDÉPRESSEURS
  申请人：HOFFMANN LA ROCHE

  公开号：WO2009003867A1

  公开（公告）日：2009-01-08

  The present invention relates to compounds of formula (I) wherein R1 is hydrogen, halogen or lower alkyl; R2 is hydrogen or amino; X-Y is -(CH2)n-, N(R)-CH2-, -O-CH2- or -S-CH2-; Ar is phenyl or naphthyl; n is 1 or 2; R is hydrogen or lower alkyl; and to their pharmaceutically active salts, with the exclusion of the racemic compound 4-benzyl-4,5-dihydro-lH-imidazole or its tautomer (CAS 131548-83-9). 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.

  本发明涉及式(I)的化合物，其中R1是氢，卤素或较低的烷基; R2是氢或氨基; X-Y是-(CH2)n-，N(R)-CH2-，-O-CH2-或-S-CH2-; Ar是苯基或萘基; n为1或2; R是氢或较低的烷基; 以及它们的药物活性盐，排除了外消旋化合物4-苄基-4,5-二氢-1H-咪唑或其互变异构体（CAS 131548-83-9）。发现式(I)的化合物对痕量胺相关受体（TAARs）具有良好的亲和力，特别是对TAAR1。这些化合物可用于治疗抑郁症、焦虑症、双相情感障碍、注意力缺陷多动障碍（ADHD）、与压力相关的障碍、精神障碍如精神分裂症、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、物质滥用和代谢障碍如进食障碍、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、体温稳态障碍和功能障碍、睡眠和昼夜节律障碍以及心血管疾病。
• 4-IMIDAZOLINES AND THEIR USE AS ANTIDEPRESSANTS
  申请人：F. Hoffmann-La Roche AG

  公开号：EP2173719A1

  公开（公告）日：2010-04-14
• US7812047B2
  申请人：——

  公开号：US7812047B2

  公开（公告）日：2010-10-12
• 4-imidazolines
  申请人：Hoffman-La Roche Inc.

  公开号：US07812047B2

  公开（公告）日：2010-10-12

  The present invention relates to compounds of formula wherein R1, R2, X, Y and Ar are as defined herein and to their pharmaceutically active salts, with the exclusion of the racemic compound 4-benzyl-4,5-dihydro-1H-imidazole or its tautomer (CAS 131548-83-9). 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、X、Y和Ar的定义如下，并且涉及它们的药物活性盐，但排除了外消旋化合物4-苄基-4,5-二氢-1H-咪唑或其互变异构体（CAS 131548-83-9）。式I的化合物具有良好的亲和力，特别是对TAAR1的痕量胺相关受体（TAARs），并可用于治疗抑郁症、焦虑症、双相情感障碍、注意力缺陷多动障碍（ADHD）、与压力相关的障碍、精神障碍如精神分裂症、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、物质滥用和代谢性疾病如进食障碍、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、体温稳态障碍和功能障碍、睡眠和昼夜节律障碍以及心血管疾病。