2-(4-chlorophenylaminomethyl)imidazoline | 67083-84-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(4-chlorophenylaminomethyl)imidazoline
• 英文别名: 4-chloro-N-(4,5-dihydro-1H-imidazol-2-ylmethyl)-aniline；(4-chloro-phenyl)-(4,5-dihydro-1H-imidazol-2-ylmethyl)-amine；4-chloro-N-(4,5-dihydro-1H-imidazol-2-ylmethyl)aniline
• CAS: 67083-84-5
• 化学式: C₁₀H₁₂ClN₃
• 分子量: 209.678
• InChiKey: GVEGCDQUCJCZLJ-UHFFFAOYSA-N

物化性质

• 沸点：
  454.6±25.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  36.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  光气 、 2-(4-chlorophenylaminomethyl)imidazoline 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以59%的产率得到6-(4-Chloro-phenyl)-2,3,6,7-tetrahydro-imidazo[1,5-a]imidazol-5-one
  参考文献：
  名称：

  Aminoamidines

  摘要：

  N-Aryl-substituted 5-oxo-tetrahydroimidazo[1,5-a]imidazoles, tetrahydroimidazo[1,2-c][1,3,2 lambda(3)]- and -[1,2-c][1,3,2 lambda(5)]diazaphospholes, as well as 6-ore- and 5,6-dioxohexahydroimidazo[1, 2-a]pyrazines were synthesized using 2-arylaminomethylimidazolines as 1,4-binucleophiles.

  DOI：

  10.1007/bf01169723
• 作为产物：
  描述：

  [(4-氯苯基)氨基]乙腈 、 乙二胺 在 tetraphosphorus decasulfide 作用下， 反应 1.5h， 以83%的产率得到2-(4-chlorophenylaminomethyl)imidazoline
  参考文献：
  名称：

  Aminoamidines

  摘要：

  2-(Arylaminomethyl)imidazolines were prepared by the reaction of arylaminoacetonitriles with ethylenediamine in the presence of catalytic amounts of P2S5 These imidazolines react with aroyl chlorides (1 : 2 ratio) to give diacylation products. In the case of a 1 : 1 mole ratio as well as on treatment with Ac2O in Et(3)N, monoacylation at the imidazoline ring predominantly occurs. Isomeric 2-(N-benzoyl-N-arylaminomethyl)imidazolines were obtained from N-benzoyl-N-arylaminoacetonitriles by the Pinner method. 2-(N-Aroyl-N-arylaminomethyl)benzimidazoles and -benzoxazoles were synthesized in a similar way.

  DOI：

  10.1007/bf01169722

文献信息

• 2-IMIDAZOLINES
  申请人：Galley Guido

  公开号：US20090018180A1

  公开（公告）日：2009-01-15

  The present invention relates to compounds of formula I wherein X—Y, R 1 , and n are as defined herein and to their pharmaceutically 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X—Y、R1和n如本文所定义，并且涉及它们的药用活性盐。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，适用于治疗抑郁症、焦虑障碍、双相情感障碍、注意力缺陷多动障碍（ADHD）、与压力有关的障碍、精神分裂症等精神障碍、帕金森病等神经系统疾病、阿尔茨海默病等神经退行性疾病、癫痫、偏头痛、高血压、物质滥用以及代谢性障碍，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、睡眠和昼夜节律障碍，以及心血管疾病。
• 2-IMIDAZOLINES HAVING A GOOD AFFINITY TO THE TRACE AMINE ASSOCIATED RECEPTORS (TAARS)
  申请人：F. Hoffmann-La Roche AG

  公开号：EP2173720A2

  公开（公告）日：2010-04-14
• TRACE AMINE ASSOCIATED RECEPTOR 1 AGONISTS AND PARTIAL AGONISTS FOR PAIN TREATMENT
  申请人：Purdue Pharma LP

  公开号：EP3463359A1

  公开（公告）日：2019-04-10
• US7652055B2
  申请人：——

  公开号：US7652055B2

  公开（公告）日：2010-01-26
• [EN] 2-IMIDAZOLINES<br/>[FR] 2-IMIDAZOLINES
  申请人：HOFFMANN LA ROCHE

  公开号：WO2009003868A2

  公开（公告）日：2009-01-08

  The present invention relates to compounds of formula (I) wherein X-Y is -N(R2) -CH(R3)-, CH(R3)-N(R2)-, -NH-NH-, -O-CHR3-, -CHR3-O-, -S-CHR3, -CHR3-S- or -CHR3-CHR3 -; R1 is hydrogen, halogen, lower alkyl, lower alkoxy, -(CH2)o-phenyl optionally substituted by lower alkoxy, -(CH2)o-C(O)-phenyl optionally substituted by lower alkoxy, -(CH2)o-O-phenyl optionally substituted by lower alkoxy, -(CH2)o-O-phenyl, CF3, cycloalkyl, NO2, amino or hydroxy; R2 is hydrogen, lower alkyl, phenyl optionally substituted by hydroxy or benzyl; R3/R3' are independently from each other hydrogen, lower alkyl or benzyl; Ar is phenyl, naphthyl, benzofuranyl or benzo [1,3] dioxolyl; n is 1, 2, 3 or 4; o is 0, 1, 2, 3 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.