Abaperidone hydrochloride | 183849-45-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: Abaperidone hydrochloride
• 英文别名: 7-[3-[4-(6-Fluoro-1,2-benzisoxazole-3-yl)piperidin-1-yl]propoxy]-3-(hydroxymethyl)-chromen-4-one hydrochloride；7-[3-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]propoxy]-3-(hydroxymethyl)chromen-4-one;hydrochloride
• CAS: 183849-45-8
• 化学式: C₂₅H₂₅FN₂O₅*ClH
• 分子量: 488.943
• InChiKey: FUKIEXAUUAYHPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.64
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  85
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Abaperidone hydrochloride 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以43%的产率得到7-[3-[4-(6-fluorobenzo[d]isoxazole-3-yl)piperidine-1-yl]propoxy]-3-formyl-chromen-4-one
  参考文献：
  名称：

  7-[3-(1-Piperidinyl)propoxy]chromenones as Potential Atypical Antipsychotics. 2. Pharmacological Profile of 7-[3-[4-(6-Fluoro-1,2-benzisoxazol-3-yl)-piperidin-1-yl]propoxy]-3-(hydroxymethyl)chromen-4-one (Abaperidone, FI-8602)

  摘要：

  A series of novel 7-[3-(1-piperidinyl)propoxy]chromenones was synthesized and tested as potential antipsychotics in several in vitro and in vivo assays. The compounds possessed good affinity for Dp receptors, together with a greater affinity for 5-HT2 receptors, a profile which has been proposed as a model for atypical antipsychotics. Several agents also displayed a high potency in the climbing mice assay on oral administration, suggesting a potent antipsychotic effect as compared to reference standards. Compound 23 was selected for fur ther pharmacological evaluation. induction of catalepsy and inhibition of stereotypies weaker than standards, along with a lower increase in serum prolactin levels, were indicative of a potential atypical profile for this compound. From these results, 7-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidin-1-yl]propoxy]-3-(hydroxymethyl)chromen-4-one (23, abaperidone) has been proposed for clinical evaluation in humans as a potential atypical antipsychotic.

  DOI：

  10.1021/jm9810396

文献信息

• [EN] 4-(6-FLUORO-1,2-BENZISOXAZOLYL)-1-PIPERIDINYL-PROPOXY-CHROMEN-4-ONE DERIVATIVES, THEIR PREPARATION AND THEIR USE IN THE TREATMENT OF PSYCHOSIS, SCHIZOPHRENIA AND ANXIETY<br/>[FR] DERIVES DE 4-(6-FLUORO-1,2-BENZISOXAZOLYL)-1-PIPERIDINYL-PROPOXY-CHROMEN-4-ONE, LEUR PREPARATION ET LEUR UTILISATION DANS LE TRAITEMENT DES PSYCHOSES, DE LA SCHIZOPHRENIE ET DE L'ANXIETE
  申请人：FERRER INTERNACIONAL, S.A.

  公开号：WO1996032389A1

  公开（公告）日：1996-10-17

  (EN) The present invention relates to 4-(6-fluoro-1,2-benzisoxazolyl)-1-piperidinyl-propoxy-chromen-4-one derivatives having formula (I), wherein R is hydrogen or alkyl having 1 to 4 carbon atoms optionally substituted by hydroxyl, as well as their pharmaceutically acceptable addition salts, which are useful in the treatment of psychosis, schizophrenia and anxiety.(FR) La présente invention décrit des dérivés de 4-(6-fluoro-1,2-benzisoxazolyl)-1-pipéridinyl-propoxy-chromen-4-one de formule (I), dans laquelle R représente hydrogène ou alkyle ayant de 1 à 4 atomes de carbone facultativement substitués par hydroxyle, ainsi que leurs sels d'addition pharmaceutiquement acceptables, utilisés dans le traitement des psychoses, de la schizophrénie et de l'anxiété.

  本发明涉及具有式(I)的4-(6-氟-1,2-苯并异噁唑基)-1-哌啶基-丙氧基-香豆素衍生物，其中R为氢或烷基，烷基含有1至4个碳原子，可选择地被羟基取代，以及它们的药学上可接受的加合物盐，用于治疗精神病、精神分裂症和焦虑症。
• 4-(6-FLUORO-1,2-BENZISOXAZOLYL)-1-PIPERIDINYL-PROPOXY-CHROMEN-4-ONE DERIVATIVES, THEIR PREPARATION AND THEIR USE IN THE TREATMENT OF PSYCHOSIS, SCHIZOPHRENIA AND ANXIETY
  申请人：FERRER INTERNACIONAL, S.A.

  公开号：EP0765323A1

  公开（公告）日：1997-04-02