5-Amino-1-(3-dimethylaminopropyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran

• 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: 5-Amino-1-(3-dimethylaminopropyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran
• 英文别名: 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-3H-2-benzofuran-5-amine
• 化学式: C₁₉H₂₃FN₂O
• 分子量: 314.403
• InChiKey: BVSMMUHIUOQJRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  38.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-Amino-1-(3-dimethylaminopropyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran 在 CuCN NaCN 、 硫酸 、 sodium carbonate 、 sodium nitrite 作用下， 以 水 、 甲苯 为溶剂， 以32%的产率得到西酞普兰
  参考文献：
  名称：

  Method for the preparation of citalopram

  摘要：

  描述了一种西酞普兰的制备方法，包括将式（IV）中R1为H或C1-6烷基羰基的化合物与4-卤代氟苯基的格氏试剂和3-卤代-N，N-二甲基丙胺的格氏试剂依次反应，使得式（IV）的产物发生环闭合反应，并将得到的1,3-二氢异苯并呋喃化合物转化为相应的5-氰基衍生物，即西酞普兰。

  公开号：

  US06258842B1

文献信息

• METHOD FOR THE PREPARATION OF CITALOPRAM
  申请人：H. LUNDBECK A/S

  公开号：EP1042310A2

  公开（公告）日：2000-10-11
• Antidepressant Medicament Comprising Idazoxan and a Selective Serotonin Reuptake Inhibitor
  申请人：Svensson Torgny

  公开号：US20080269306A1

  公开（公告）日：2008-10-30

  Use of Idazoxan or an active enantiomer thereof, and treatment of patients receiving therapy with selective serotonin uptake inhibitor(s), such as Fluoxetine, Citalopram, Paroxetine, Sertraline and Fluvoxamine, are described. The patients being treated are in particular those who are suffering from severe depression, anxiety-depression, PTSD (Post Traumatic Stress Disorder), or ADHD (Attention Deficit Hyperactive Disorder).
• US6258842B1
  申请人：——

  公开号：US6258842B1

  公开（公告）日：2001-07-10
• [EN] METHOD FOR THE PREPARATION OF CITALOPRAM<br/>[FR] PROCEDE DE PREPARATION DE CITALOPRAME
  申请人：——

  公开号：WO1998019512A2

  公开（公告）日：1998-05-14

  [EN] A method for the preparation of citalopram is described comprising reaction of a compound of Formula (IV) wherein R<1> is H or C1-6alkylcarbonyl successively with a Grignard reagent of 4-halogen-fluorophenyl and a Grignard reagent of 3-halogen-N,N-dimethylpropylamine, effecting ring closure of the resulting compound of Formula (VI) and converting the resulting 1,3-dihydroisobenzofuran compound to the corresponding 5-cyano derivative, i.e. citalopram.
  [FR] L'invention concerne un procédé de préparation de citaloprame consistant à faire réagir un composé de la formule (IV), dans laquelle R<1> représente H ou C1-6 alkylcarbonyle, successivement, avec un réactif de Grignard de 4-halogèno-fluorophényle et un réactif de Grignard de 3-halogèno-N,N-diméthylpropylamine, à effectuer la cyclisation du composé obtenu de formule (VI), et à transformer le composé 1,3-dihydoisobenzofuranne obtenu en son dérivé 5-cyano correspondant, c'est-à-dire en citaloprame.
• [EN] QUATERNARY AMMONIUM SALT PRODRUGS<br/>[FR] PROMÉDICAMENTS CONTENANT DES SELS D'AMMONIUM QUATERNAIRE
  申请人：ALKERMES INC

  公开号：WO2011084846A1

  公开（公告）日：2011-07-14

  The invention provides a method of sustained delivery of a tertiary amine-containing parent drug comprising administering to a patient an effective amount of a prodrug compound of the invention wherein upon administration to the patient, release of the parent drug from the prodrug is sustained release. Prodrug compounds suitable for use in the methods of the invention are labile quaternary ammonium salts of tertiary amine-containing parent drugs (or tertiary imine-containing parent drugs) that are derivatized through aldehyde-linked prodrug moieties that reduce the solubility of the prodrug compound at a reference pH as compared to the parent drug. The physical, chemical and solubility properties of these derivatives can be further modulated by the choice of counterion X". In one embodiment, the present invention provides a prodrug compound of Formula I: where R1-R5 are defined in the written description of the invention. The prodrug compounds of the invention can be used to treat any condition for which the tertiary amine-containing parent drug or tertiary imine-containing parent drug is useful as a treatment.