Butyrophenone, 4-(4-benzylpiperidino)-4'-fluoro-, hydrochloride | 35623-05-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: Butyrophenone, 4-(4-benzylpiperidino)-4'-fluoro-, hydrochloride
• 英文别名: 4-(4-benzylpiperidin-1-yl)-1-(4-fluorophenyl)butan-1-one;hydrochloride
• CAS: 35623-05-3
• 化学式: C₂₂H₂₆FNO*ClH
• 分子量: 375.914
• InChiKey: JRGPLXNYZSSQEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.17
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  20.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Butyrophenone, 4-(4-benzylpiperidino)-4'-fluoro-, hydrochloride 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 4-(4-Benzylpiperidin-1-yl)-1-(4-fluorophenyl)butan-1-ol
  参考文献：
  名称：

  7-[3-(1-Piperidinyl)propoxy]chromenones as Potential Atypical Antipsychotics

  摘要：

  Compound 1 (1-benzyl-3-methyl-4-[4-(4-fluorophenyl)- a synthetic intermediate identified as a potential atypical antipsychotic, was selected as the starting point for pharmacological improvement. From 1, sequential structural variations were conducted in order to improve its potency and oral bioavailability. These variations included a series of piperazine, ethanediamine, and piperidine derivatives. The piperidine series afforded some orally potent compounds in the inhibition of apomorphine-induced climbing and hyperactivity in mice, which are regarded as behavioral models predictive of antipsychotic efficacy. Further optimization of these structures led to the highly potent 7-[3-(1-piperidinyl)propoxy]chromenones. Inhibition of stereotypies and induction of catalepsy in rats at doses substantially higher than required for inhibition of climbing suggest an atypical antipsychotic profile, which is assumed to predict a reduced induction of extrapyramidal side effects in humans.

  DOI：

  10.1021/jm950894b
• 作为产物：
  描述：

  4-苄基哌啶 在 盐酸 、 potassium carbonate 、 potassium iodide 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 26.0h， 生成 Butyrophenone, 4-(4-benzylpiperidino)-4'-fluoro-, hydrochloride
  参考文献：
  名称：

  7-[3-(1-Piperidinyl)propoxy]chromenones as Potential Atypical Antipsychotics

  摘要：

  Compound 1 (1-benzyl-3-methyl-4-[4-(4-fluorophenyl)- a synthetic intermediate identified as a potential atypical antipsychotic, was selected as the starting point for pharmacological improvement. From 1, sequential structural variations were conducted in order to improve its potency and oral bioavailability. These variations included a series of piperazine, ethanediamine, and piperidine derivatives. The piperidine series afforded some orally potent compounds in the inhibition of apomorphine-induced climbing and hyperactivity in mice, which are regarded as behavioral models predictive of antipsychotic efficacy. Further optimization of these structures led to the highly potent 7-[3-(1-piperidinyl)propoxy]chromenones. Inhibition of stereotypies and induction of catalepsy in rats at doses substantially higher than required for inhibition of climbing suggest an atypical antipsychotic profile, which is assumed to predict a reduced induction of extrapyramidal side effects in humans.

  DOI：

  10.1021/jm950894b

文献信息

• 4-Benzylpiperidine derivatives, a process for preparing them and pharmaceutical compositions containing them
  申请人：FERRER INTERNACIONAL, S.A.

  公开号：EP0572952A1

  公开（公告）日：1993-12-08

  4-Benzylpiperidine derivatives of the formula: or a pharmaceutically accpetable acid addition salt thereof, wherein X is hydrogen or fluorine and R is hydrogen, or a group selected from p-fluorobenzoyl, alpha-hydroxy-p-fluorobenzyl, p-fluorophenoxy, bis(p-fluorophenyl)methyl and 8-azaspiro [4,5] decane-7,9-dione-8-yl-methyl with the proviso that X and R may not be simultaneously hydrogen and p-fluorobenzoyl respectively. Such compounds are useful as sigma-receptor ligands.

  式中的 4-苄基哌啶衍生物： 或其可药用的酸加成盐，其中 X 为氢或氟，R 为氢或选自对氟苯甲酰基、α-羟基-对氟苄基、对氟苯氧基、双（对氟苯基）甲基和 8-氮杂螺[4,5]癸烷-7,9-二酮-8-基-甲基的基团，但 X 和 R 不得分别同时为氢和对氟苯甲酰基。 此类化合物可用作σ受体配体。
• US5395841A
  申请人：——

  公开号：US5395841A

  公开（公告）日：1995-03-07
• 7-[3-(1-Piperidinyl)propoxy]chromenones as Potential Atypical Antipsychotics
  作者：Jordi Bolós、Santiago Gubert、Lluís Anglada、Josep M. Planas、Carme Burgarolas、Josep M. Castelló、Aurelio Sacristán、José A. Ortiz

  DOI：10.1021/jm950894b

  日期：1996.1.1

  Compound 1 (1-benzyl-3-methyl-4-[4-(4-fluorophenyl)- a synthetic intermediate identified as a potential atypical antipsychotic, was selected as the starting point for pharmacological improvement. From 1, sequential structural variations were conducted in order to improve its potency and oral bioavailability. These variations included a series of piperazine, ethanediamine, and piperidine derivatives. The piperidine series afforded some orally potent compounds in the inhibition of apomorphine-induced climbing and hyperactivity in mice, which are regarded as behavioral models predictive of antipsychotic efficacy. Further optimization of these structures led to the highly potent 7-[3-(1-piperidinyl)propoxy]chromenones. Inhibition of stereotypies and induction of catalepsy in rats at doses substantially higher than required for inhibition of climbing suggest an atypical antipsychotic profile, which is assumed to predict a reduced induction of extrapyramidal side effects in humans.