α-bromo-3,4-dichlorophenylacetic acid methyl ester | 163339-71-7

• 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: α-bromo-3,4-dichlorophenylacetic acid methyl ester
• 英文别名: methyl 1-(3,4-dichlorophenyl)-1-bromoacetate；Methyl 2-(3,4-dichlorophenyl)-2-bromoacetate；methyl 2-bromo-2-(3,4-dichlorophenyl)acetate
• CAS: 163339-71-7
• 化学式: C₉H₇BrCl₂O₂
• 分子量: 297.963
• InChiKey: GJCPCGAKJFTMFO-UHFFFAOYSA-N

物化性质

• 沸点：
  316.7±37.0 °C(Predicted)
• 密度：
  1.654±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  α-bromo-3,4-dichlorophenylacetic acid methyl ester 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 2-(3,4-二氯苯基)-哌嗪
  参考文献：
  名称：

  Synthesis and NK1/NK2 binding activities of a series of diacyl-substituted 2-arylpiperazines

  摘要：

  The synthesis and binding affinity for hNK(1) and hNK(2) receptors of a series of diacyl substituted 2-aryl piperazines are described. SAR evaluation led to the racemic derivative 11g as an apparent dual inhibitor. Chiral chromatographic separation of 11g led to the observation that NK1 activity was shown by one enantiomer (13a) and NK2 activity was shown by the other enantiomer (13b). X-ray crystallographic analysis of the crystalline di-BOC derivative of the NK2, active piperazine (15) showed that the 2R configuration was associated with NK2 activity. Further derivatization indicated that dual NK1/NK2 activity could be built into the 2R series. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00645-5
• 作为产物：
  描述：

  3,4-二氯苯乙酸甲酯 在 1,3-二溴-5,5-二甲基海因 、 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile 作用下， 以 1,1-二氯乙烷 为溶剂， 反应 7.5h， 生成 α-bromo-3,4-dichlorophenylacetic acid methyl ester
  参考文献：
  名称：

  Novel polymorphs of azabicyclohexane

  摘要：

  这项发明提供了(+) -1-(3,4-二氯苯基)-3-氮杂双环[3.1.0]己烷的多形晶体酸加盐形式，分别被指定为多形式A、多形式B和多形式C，其中多形式A比其他形式更具热力学稳定性，还提供了制备和使用这些多形式以及含有这些多形式的药物组合物的方法。

  公开号：

  US20070043100A1

文献信息

• [EN] PREPARATION AND USE OF (+)-1-(3,4-DICHLOROPHENYL)-3-AZABICYCLO[3.1.0]HEXANE IN THE TREATMENT OF CONDITIONS AFFECTED BY MONOAMINE NEUROTRANSMITTERS<br/>[FR] PRÉPARATION ET UTILISATION DU (+)-1-(3,4-DICHLOROPHÉNYL)-3-AZABICYCLO- [3.1.0]HEXANE DANS LE TRAITEMENT DES PATHOLOGIES AFFECTÉES PAR LES NEUROTRANSMETTEURS DE TYPE MONOAMINE
  申请人：EUTHYMIC BIOSCIENCE INC

  公开号：WO2012075473A1

  公开（公告）日：2012-06-07

  The present invention relates to (+)-1-(3,4-dichlorophenyl)-3-azabicyclo[3.1.0]hexane and pharmaceutically acceptable active salts, polymorphs, glycosylated derivatives, metabolites, solvates, hydrates, and/or prodrugs of (+)-1-(3,4-dichlorophenyl)-3-azabicyclo[3.1.0]hexane and their use alone or in combination with additional psychotherapeutic compositions in the treatment of conditions affected by monoamine neurotransmitters, including treatment of refractory individuals.

  本发明涉及(+)-1-(3,4-二氯苯基)-3-氮杂双环[3.1.0]己烷及其药用可接受的活性盐、多型、糖基化衍生物、代谢物、溶剂合物、水合物和/或前药，以及其单独使用或与其他心理治疗组合物结合在一起用于治疗受单胺神经递质影响的疾病的用途，包括治疗难治性个体。
• USE OF AMITIFADINE, (+)-1-(3,4-DICHLOROPHENYL)-3-AZABICYCLO[3.1.0]HEXANE IN METHODS AND COMPOSITIONS WITH ENHANCED EFFICACY AND REDUCED METABOLIC SIDE EFFECTS AND TOXICITY FOR TREATMENT OF DEPRESSION AND OTHER CENTRAL NERVOUS SYSTEM DISORDERS AND CONDITIONS AFFECTED BY MONOAMINE NEUROTRANSMITTERS
  申请人：McKinney Anthony Alexander

  公开号：US20160346249A1

  公开（公告）日：2016-12-01

  The present invention relates to (+)-1-(3,4-dichlorophenyl)-3-azabicyclo[3.1.0]hexane and pharmaceutically acceptable active salts, polymorphs, glycosylated derivatives, metabolites, solvates, hydrates, and/or prodrugs of (+)-1-(3,4-dichlorophenyl)-3-azabicyclo[3.1.0]hexane and their use alone or in combination with additional psychotherapeutic compositions in the treatment of conditions affected by monoamine neurotransmitters, including treatment of refractory individuals. (+)-1-(3,4-dichlorophenyl)-3-azabicyclo[3.1.0]hexane compositions are metabolized by either or both MAO-A or cytochrome P450 enzymes and thus are effective in the treatment of individuals with cytochrome P450 polymorphisms or who are taking other medications that affect the cytochrome P450 pathway.

  本发明涉及（+）-1-（3,4-二氯苯基）-3-氮杂双环[3.1.0]己烷及其药用可接受的活性盐、多晶形态、糖基化衍生物、代谢物、溶剂合物、水合物和/或前药，以及其单独使用或与额外的精神疗法组合一起治疗受单胺神经递质影响的疾病，包括难治性个体的治疗。 （+）-1-（3,4-二氯苯基）-3-氮杂双环[3.1.0]己烷组合物被MAO-A或细胞色素P450酶中的任一或两者代谢，因此对患有细胞色素P450多态性或正在服用影响细胞色素P450途径的其他药物的个体进行治疗是有效的。
• Dual NK1 antagonists—serotonin reuptake inhibitors as potential antidepressants. Part 2: SAR and activity of benzyloxyphenethyl piperazine derivatives
  作者：Thomas Ryckmans、Olivier Berton、Renée Grimée、Thierry Kogej、Yves Lamberty、Patrick Pasau、Patrice Talaga、Christophe Genicot

  DOI：10.1016/s0960-894x(02)00563-2

  日期：2002.11

  piperazine derivatives combining NK(1) antagonism and serotonin reuptake inhibition is described. Compound 7u was shown to be active in animal models of 5-HT reuptake inhibition and central NK(1) receptor blockade, and was demonstrated to be orally active in an integrated model sensitive to both mechanisms. This class of compounds potentially represents a new generation of antidepressants.

  描述了结合NK（1）拮抗作用和5-羟色胺再摄取抑制作用的苄氧基苯乙基哌嗪衍生物的合成，结构亲和关系和活性。化合物7u在抑制5-HT再摄取和中枢NK（1）受体的动物模型中显示出活性，并在对两种机制均敏感的综合模型中显示出口服活性。这类化合物可能代表了新一代的抗抑郁药。
• Chemical compounds
  申请人：——

  公开号：US20030028021A1

  公开（公告）日：2003-02-06

  The invention relates to piperazine derivatives, to processes for their preparation, to pharmaceutical compositions containing them, and to their medical use. The novel compounds are antagonists of tachykinins, including substance P and other neurokinins.

  本发明涉及哌嗪衍生物、其制备方法、包含它们的制药组合物以及它们的医疗用途。这些新化合物是缓解速激肽素（包括物质P和其他神经激肽素）的拮抗剂。
• METHODS AND COMPOSITIONS FOR PRODUCTION, FORMULATION AND USE OF 1 ARYL-3-AZABICYCLO[3.1.0]HEXANES
  申请人：Chen Zhengming

  公开号：US20080058535A1

  公开（公告）日：2008-03-06

  The invention provides novel compositions and methods of making (−)-1-(3,4-dichlorophenyl)-3-azabicyclo[3.1.0]hexane and other 1-aryl-3-azabicyclo[3.1.0]hexanes, including synthetic methods that form novel intermediate compounds of the invention for producing)-(−)-1-(3,4-dichlorophenyl)-3-azabicyclo[3.1.0]hexane and other 1-aryl-3-azabicyclo[3.1.0]hexanes and pharmaceutically acceptable salts thereof.

  本发明提供了制备(-)-1-(3,4-二氯苯基)-3-氮杂双环[3.1.0]己烷和其他1-芳基-3-氮杂双环[3.1.0]己烷的新型组合物和制备方法，包括形成本发明的新型中间化合物的合成方法，用于生产(-)-1-(3,4-二氯苯基)-3-氮杂双环[3.1.0]己烷和其他1-芳基-3-氮杂双环[3.1.0]己烷及其药学上可接受的盐。