N-(2-(2-甲氧基苯氧基)乙基)苄胺盐酸盐 | 3246-03-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(2-(2-甲氧基苯氧基)乙基)苄胺盐酸盐
• 中文别名: N-[2-(2-甲氧基苯氧基)乙基]苄胺盐酸盐
• 英文名称: N-[2-(2'-(methoxy)-phenoxy)-ethyl]-benzylamine
• 英文别名: N-[2-(2-methoxyphenoxy)ethyl]benzylamine；N-benzyl-2-(2-methoxyphenoxy)ethanamine；benzyl[2-(2-methoxyphenoxy)ethyl]amine；[2-(2-methoxy-phenoxy)-ethyl]-benzyl-amine；N-[2-(2'--phenoxy)-ethyl]-benzylamine；N-[2-(2-methoxy-phenoxy)ethyl]-benzylamine；N-Benzyl-2-(2-methoxyphenoxy)ethylamine
• CAS: 3246-03-5
• 化学式: C₁₆H₁₉NO₂
• mdl: MFCD11923811
• 分子量: 257.332
• InChiKey: SZDYRZVWNVIYGO-UHFFFAOYSA-N

物化性质

• 沸点：
  160-161 °C(Press: 0.3 Torr)
• 密度：
  1.072±0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2922299090

反应信息

• 作为反应物：
  描述：

  N-(2-(2-甲氧基苯氧基)乙基)苄胺盐酸盐 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 36.0h， 生成 [3-(5-Fluoro-1H-indol-3-yl)-propyl]-[2-(2-Methoxy-phenoxy)ethyl]-amine
  参考文献：
  名称：

  Studies toward the Discovery of the Next Generation of Antidepressants. 3. Dual 5-HT_1A and Serotonin Transporter Affinity within a Class of N-Aryloxyethylindolylalkylamines

  摘要：

  N-Aryloxylethylindolealkylamines (5) having dual 5-HT transporter and 5-HT1A affinity are described. These compounds represent truncated analogues of our previously reported piperidinyl derivatives (3). Compounds in this investigation were found to have more similar affinities and functional activities for the 5-HT1A receptor and 5-HT transporter. Though 5-HT1A antagonism is not consistently observed throughout series 5, several molecular features were found to be essential to obtain high and balanced activities. The proper placement of a heteroatom in the aryl ring and the length of the linkage used to tether the indole moiety had significant influence on 5-HT1A and 5-HT transporter affinities. Introduction of a halogen into the aryl ring usually lowered intrinsic activity and in some cases led to full 5-HT1A antagonists. Compounds 33 and 34 were observed to be full 5-HT1A antagonists with K-i values of approximately 30 nM for the 5-HT1A receptor and K-i values of 5 and 0.5 nM for the 5-HT transporter, respectively. Unfortunately, similar to our previous series (3), compounds in this report also had high affinity for the alpha(1) receptor.

  DOI：

  10.1021/jm0304010
• 作为产物：
  描述：

  N-[2-(2-methoxyphenoxy)ethyl]-N-benzylcarbamic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以96%的产率得到N-(2-(2-甲氧基苯氧基)乙基)苄胺盐酸盐
  参考文献：
  名称：

  Studies toward the Discovery of the Next Generation of Antidepressants. 3. Dual 5-HT_1A and Serotonin Transporter Affinity within a Class of N-Aryloxyethylindolylalkylamines

  摘要：

  N-Aryloxylethylindolealkylamines (5) having dual 5-HT transporter and 5-HT1A affinity are described. These compounds represent truncated analogues of our previously reported piperidinyl derivatives (3). Compounds in this investigation were found to have more similar affinities and functional activities for the 5-HT1A receptor and 5-HT transporter. Though 5-HT1A antagonism is not consistently observed throughout series 5, several molecular features were found to be essential to obtain high and balanced activities. The proper placement of a heteroatom in the aryl ring and the length of the linkage used to tether the indole moiety had significant influence on 5-HT1A and 5-HT transporter affinities. Introduction of a halogen into the aryl ring usually lowered intrinsic activity and in some cases led to full 5-HT1A antagonists. Compounds 33 and 34 were observed to be full 5-HT1A antagonists with K-i values of approximately 30 nM for the 5-HT1A receptor and K-i values of 5 and 0.5 nM for the 5-HT transporter, respectively. Unfortunately, similar to our previous series (3), compounds in this report also had high affinity for the alpha(1) receptor.

  DOI：

  10.1021/jm0304010
• 作为试剂：
  描述：

  N-(2-(2-甲氧基苯氧基)乙基)苄胺盐酸盐 、 4-环氧丙烷氧基咔唑 在 N-(2-(2-甲氧基苯氧基)乙基)苄胺盐酸盐 作用下， 以99的产率得到N-苄基卡维地洛
  参考文献：
  名称：

  [EN] PROCESS FOR THE PREPARATION OF CARVEDILOL
  [FR] PROCESSUS POUR LA PRÉPARATION DE CARVÉDILOL

  摘要：

  一种制备公式（I）的卡维地洛的方法，该方法可以制备其对映体纯形式或对映体混合物，可选地作为其药学上可接受的盐。该方法包括将公式（II）的2,3-环氧丙氧基咔唑或其R或S对映体与公式（V）的N-[2-(2-甲氧基苯氧基)乙基]-苄胺反应，得到公式（VI）的苄基卡维地洛，然后通过催化氢化去苄基，得到公式（I）的卡维地洛，可以制备其对映体纯形式或对映体混合物，如果需要，可以将所得的公式（I）的卡维地洛与无机或有机酸反应，制备其药学上可接受的盐，并/或分离对映体。上述方法的特点在于，在水中作为反应介质进行公式（II）的2,3-环氧丙氧基咔唑与公式（V）的N-[2-(2-甲氧基苯氧基)乙基]-苄胺的反应。本发明还提供了通过上述方法制备的公式（I）的卡维地洛，以及包含其的药物组合物和治疗用途。

  公开号：

  WO2005113502A1

文献信息

• Synthesis and Characterization of Potential Impurities of Carvedilol, an Antihypertensive Drug
  作者：Somisetti Narender Rao、Devarasetty Sitaramaiah、Kema Srimannarayana、Challa Nageswar Rao、Peddi Srinivasa Rao、K. Sudhakar Babu

  DOI：10.1080/00397910903531839

  日期：2010.12.21

  Carvedilol (Coreg) is a nonselective β-adrenergic blocking agent with vasodilating activity. It is used for the treatment of congestive heart failure and hypertension. During the bulk synthesis of carvedilol, we have observed six impurities: Imp-I, Imp-II, Imp-III, Imp-IV, Imp-V, and Imp-VI. The present work describes the synthesis and characterization of these impurities.

  卡维地洛 (Coreg) 是一种具有血管舒张活性的非选择性 β-肾上腺素能阻断剂。用于治疗充血性心力衰竭和高血压。在卡维地洛的批量合成过程中，我们观察到六种杂质：Imp-I、Imp-II、Imp-III、Imp-IV、Imp-V 和 Imp-VI。目前的工作描述了这些杂质的合成和表征。
• Phenoxyethylamine derivatives having high affinity for the 5-HT1A receptor, preparation thereof, use thereof as drugs, and pharmaceutical compositions containing said derivatives
  申请人：Societe de Conseils de Recherches et D'Applications Scientifiques (S.C.R.A.S.)

  公开号：US06670400B1

  公开（公告）日：2003-12-30

  Phenoxyethylamine derivatives of general formula (I) having high affinity for the 5-HT1A receptor, methods for preparing same, pharmaceutical compositions containing said derivatives, and their use, in particular as gastric acid secretion inhibitors or as antiemetics, are disclosed. In general formula (I), Ar is phenyl substituted by one or more substituents; and R is a C1-10 hydrocarbon radical selected from straight or branched alkyl, alkenyl or alkynyl radicals, saturated or unsaturated mono- or polycyclic cycloalkyl, cycloalkylalkyl or alkylcycloalkyl radicals; a pyridyl or isoquinolyl radical, phenyl optionally substituted by one or more substituents, and salts thereof.

  通式(I)的苯氧乙胺衍生物具有高亲和力5-HT1A受体，揭示了制备同样的方法，包含上述衍生物的药物组合物，以及它们的用途，特别是作为胃酸分泌抑制剂或抗恶心药物。在通式(I)中，Ar是被一个或多个取代基取代的苯基；而R是从直链或支链烷基、烯烃基或炔烃基、饱和或不饱和的单环或多环环烷基、环烷基烷基或烷基环烷基基团、吡啶基或异喹啉基、苯基（可选择地被一个或多个取代基取代）中选择的C1-10碳氢基团；以及它们的盐。
• 신규 아세틸콜린에스터라제 저해 유도체, 이의 제조방법, 및 이를 유효성분으로 함유하는 신경계 질환의 예방 또는 치료용 약학적 조성물
  申请人：Gachon University of Industry-Academic cooperation Foundation 가천대학교 산학협력단(220040376324) BRN ▼129-82-07687

  公开号：KR20180125090A

  公开（公告）日：2018-11-22

  본 발명은 신규 아세틸콜린에스터라제 저해 유도체, 이의 제조방법, 및 이를 유효성분으로 함유하는 신경계 질환의 예방 또는 치료용 약학적 조성물에 관한 것으로, 본 발명에 따른 화합물, 이의 입체 이성질체 또는 이의 약학적으로 허용 가능한 염은 아세틸콜린에스터라제의 활성을 우수하게 저해할 수 있는 바, 아세틸콜린에스터라제 관련 질환, 예를 들어 현재까지 아세틸콜린에스터라제와 상관관계가 규명된 질환, 예를 들어 신경계 질환의 예방 또는 치료용 약학적 조성물 또는 신경계 질환의 예방 또는 개선용 건강기능식품 조성물로 유용한 효과가 있다.

  本发明涉及一种新的乙酰胆碱酯酶抑制剂诱导体，其制备方法，以及包含其作为有效成分的神经系统疾病的预防或治疗药物组合物。根据本发明的化合物，其立体异构体或其药学上可接受的盐，能够优异地抑制乙酰胆碱酯酶的活性，对乙酰胆碱酯酶相关疾病，例如迄今为止已确定与乙酰胆碱酯酶相关的疾病，例如神经系统疾病的预防或治疗药物组合物或神经系统疾病的预防或改善的健康功能食品组合物具有有益效果。
• 一种制备1-(苯基(2-(2-甲氧基苯氧基)乙基)胺基)-3-氯-2-丙醇的方法
  申请人：江苏苏南药业实业有限公司

  公开号：CN106316867A

  公开（公告）日：2017-01-11

  本发明公开了一种制备卡维地洛重要中间体1-(苯基(2-(2-甲氧基苯氧基)乙基)胺基)-3-氯-2-丙醇(I)的方法，主要解决现有技术生产化合物I过程中反应物N-苯基-2-(2-甲氧基苯氧基)乙胺(II)转化率不高，产物分离困难的问题。本发明通过采用高温沸腾床反应器实现了化合物II与气态环氧氯丙烷的高转化率的亲核取代反应，同时使得原料环氧氯丙烷能及时第从体系中分离出来，实现低能耗、简单、快速地连续生产，得到的反应产物I的产率大于87％，化学纯度大于98％。
• [EN] A PROCESS FOR PREPARATION OF 1-[9H-CARBAZOL-4-YLOXY]- 3-[{2-(2-(-(METHOXY)PHENOXY)-ETHYL}-AMINO]-PROPAN-2-OL<br/>[FR] PROCEDE DE PREPARATION DE 1-[9H-CARBAZOL-4-YLOXY]- 3-[{2-(2-(-(METHOXY)PHENOXY)-ETHYL}-AMINO]-PROPANE-2-OL
  申请人：SUN PHARMACEUTICAL IND LTD

  公开号：WO2004113296A1

  公开（公告）日：2004-12-29

  The present invention provides a process for preparation of 1-[9H-carbazol-4-yloxy]-3-[2-(2-(methoxy)phenoxy)-ethyl}-amino]-propan-2-ol, a compound of formula (1) in racemic form or in the form of optically active R or S enantiomer or its pharmaceutically acceptable salt, comprising, reacting 4-(oxiranylmethoxy)-9H-carbazole, a compound of formula (2) or the R or S enantiomer thereof with a compound of formula (5), wherein R1 is benzyl or substituted benzyl group, in an aprotic organic solvent in presence of a catalyst to obtain a compound of formula (6), or the R or S enantiomer thereof, wherein R1 is as defined above. The resultant compound of formula (6) is subjected to debenzylation reaction by catalytic hydrogenation to obtain the compound of formula (1), if desired converting the resultant compound of formula (1) to a pharmaceutically acceptable salt thereof.

  本发明提供了一种制备1-[9H-咔唑基氧基]-3-[2-(2-(甲氧基)苯氧基)-乙基}-氨基]-丙醇的方法，该化合物的结构式为(1)，可以是拉氏体或光学活性R或S对映体，或其药用可接受的盐形式，包括将4-(环氧甲氧基)-9H-咔唑，结构式为(2)的化合物或其R或S对映体与结构式(5)的化合物反应，其中R1是苄基或取代苄基团，在无水有机溶剂中，在催化剂存在下，得到结构式(6)的化合物，或其R或S对映体，其中R1如上定义。得到的结构式(6)的化合物经过脱苄化反应进行催化氢化，得到结构式(1)的化合物，如果需要，将得到的结构式(1)的化合物转化为其药用可接受的盐形式。