1-(cyclopropylcarbonyl)-4-(hydroxymethyl)piperidine | 135136-14-0

• 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: 1-(cyclopropylcarbonyl)-4-(hydroxymethyl)piperidine
• 英文别名: Cyclopropyl-(4-hydroxymethyl-piperidin-1-yl)-methanone；cyclopropyl-[4-(hydroxymethyl)piperidin-1-yl]methanone
• CAS: 135136-14-0
• 化学式: C₁₀H₁₇NO₂
• 分子量: 183.25
• InChiKey: HJNFSJVIXSZFEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(cyclopropylcarbonyl)-4-(hydroxymethyl)piperidine 在 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 22.83h， 生成 [4-[(4-Chlorophenoxy)methyl]piperidin-1-yl]-cyclopropylmethanone
  参考文献：
  名称：

  Novel piperidine .sigma. receptor ligands as potential antipsychotic drugs

  摘要：

  Sigma receptor ligands represent a new class of potential antipsychotic drugs. This paper presents the structure-activity relationships leading to novel disubstituted piperidine sigma ligands, which have little or no affinity for dopamine D2 receptors. Selectivity for sigma sites over dopamine D2 or serotonin 5-HT2 receptors appears to be governed by the chemical nature of the piperidine nitrogen substituent, its distance from the basic nitrogen, and its orientation relative to the other piperidine substituent. Several of these compounds have good oral potency in some animal models used to evaluate potential antipsychotic drugs. The N-cyclopropylmethyl ketones and ethers (e.g. 6i (DuP 734), 6q, 18a, and 18n) have the best in vivo potency. Compounds 6i (DuP 734) and 6q did not cause catalepsy in the rat, even at very high doses. On the basis of the pharmacology profiles of these sigma ligands, we propose these compounds may be effective antipsychotic drugs, which do not induce extrapyramidal side effects or tardive dyskinesia.

  DOI：

  10.1021/jm00101a012
• 作为产物：
  描述：

  1-cyclopropylformyl-4-piperidine carboxylic acidethyl ester 在 锂硼氢 、 硼酸三甲酯 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以64%的产率得到1-(cyclopropylcarbonyl)-4-(hydroxymethyl)piperidine
  参考文献：
  名称：

  Novel piperidine .sigma. receptor ligands as potential antipsychotic drugs

  摘要：

  Sigma receptor ligands represent a new class of potential antipsychotic drugs. This paper presents the structure-activity relationships leading to novel disubstituted piperidine sigma ligands, which have little or no affinity for dopamine D2 receptors. Selectivity for sigma sites over dopamine D2 or serotonin 5-HT2 receptors appears to be governed by the chemical nature of the piperidine nitrogen substituent, its distance from the basic nitrogen, and its orientation relative to the other piperidine substituent. Several of these compounds have good oral potency in some animal models used to evaluate potential antipsychotic drugs. The N-cyclopropylmethyl ketones and ethers (e.g. 6i (DuP 734), 6q, 18a, and 18n) have the best in vivo potency. Compounds 6i (DuP 734) and 6q did not cause catalepsy in the rat, even at very high doses. On the basis of the pharmacology profiles of these sigma ligands, we propose these compounds may be effective antipsychotic drugs, which do not induce extrapyramidal side effects or tardive dyskinesia.

  DOI：

  10.1021/jm00101a012

文献信息

• Antipsychotic 1-cycloalkylpiperidines
  申请人：The Du Pont Merck Pharmaceutical Company

  公开号：US05243048A1

  公开（公告）日：1993-09-07

  There are provided cycloalkyl piperidine compounds which are useful in the treatment of physiological or drug-induced psychosis or dyskinesia in a mammal. These novel compounds are selective sigma receptor antagonists and have a low potential for movement disorder side effects associated with typical antipsychotic agents.

  提供了环状烷基哌啶化合物，用于治疗哺乳动物的生理或药物诱导的精神病或运动障碍。这些新型化合物是选择性sigma受体拮抗剂，具有与典型抗精神病药物相关的运动障碍副作用低的潜力。
• Treatment of psychosis using 1-cycloalkylpiperidines
  申请人：The Du Pont Merck Pharmaceutical Company

  公开号：US05296479A1

  公开（公告）日：1994-03-22

  There are provided cycloalkyl piperidine compounds which are useful in the treatment of physiological or drug-induced psychosis or dyskinesia in a mammal. These novel compounds are selective sigma receptor antagonists and have a low potential for movement disorder side effects associated with typical antipsychotic agents.

  提供了环状烷基哌啶化合物，可用于治疗哺乳动物的生理或药物诱导的精神病或运动障碍。这些新型化合物是选择性sigma受体拮抗剂，与典型抗精神病药物相关的运动障碍副作用潜力较低。
• ANTIPSYCHOTIC 1-CYCLOALKYLPIPERIDINES
  申请人：THE DU PONT MERCK PHARMACEUTICAL COMPANY

  公开号：EP0490962A1

  公开（公告）日：1992-06-24
• EP0490962A4
  申请人：——

  公开号：EP0490962A4

  公开（公告）日：1993-03-03
• GUANIDINE COMPOUND
  申请人：Astellas Pharma Inc.

  公开号：EP3002278B1

  公开（公告）日：2017-04-19