1-[1-(2,3-dihydrobenzo[b]furan-7-yl)piperid-4-yl]methylamine | 170353-56-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: 1-[1-(2,3-dihydrobenzo[b]furan-7-yl)piperid-4-yl]methylamine
• 英文别名: [1-(2,3-Dihydro-1-benzofuran-7-yl)piperidin-4-yl]methanamine
• CAS: 170353-56-7
• 化学式: C₁₄H₂₀N₂O
• 分子量: 232.326
• InChiKey: VNNMNJNIUXMGPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  38.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-羟甲基-1,4-苯并二噁烷对甲苯磺酸酯 、 1-[1-(2,3-dihydrobenzo[b]furan-7-yl)piperid-4-yl]methylamine 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 72.0h， 生成 (2,3-Dihydro-benzo[1,4]dioxin-2-ylmethyl)-[1-(2,3-dihydro-benzofuran-7-yl)-piperidin-4-ylmethyl]-amine
  参考文献：
  名称：

  N-Substituted (2,3-Dihydro-1,4-benzodioxin-2-yl)methylamine Derivatives as D₂ Antagonists/5-HT_1A Partial Agonists with Potential as Atypical Antipsychotic Agents

  摘要：

  A series of N-substituted 1-(2,3-dihydro-1,4-benzodioxin-2-yl)methylamine derivatives with D-2 antagonist/5-HT1A partial agonist activity has been prepared as potential atypical antipsychotic agents. Optimization of in vitro receptor binding activity and in vivo activity in rodent models of psychosis has led to compound 24, which showed good affinities for human D-2, D-3, and 5-HT1A receptors but significantly less affinity for human alpha(1) adrenoceptors and rat H-1 and muscarinic receptors. In rodents, 24 showed functional D-2-like antagonism and 5-HT1A partial agonism. After oral dosing, 24 showed good activity in rodent antipsychotic tests and very little potential to cause extrapyramidal side effects (EPS), as measured by its ability to induce catalepsy in rats only at very high doses. In the light of this promising profile of activity, 24 has been selected for clinical investigation as a novel antipsychotic agent with a predicted low propensity to cause EPS.

  DOI：

  10.1021/jm9910122
• 作为产物：
  描述：

  4-吡啶甲酰胺 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 反应 52.0h， 生成 1-[1-(2,3-dihydrobenzo[b]furan-7-yl)piperid-4-yl]methylamine
  参考文献：
  名称：

  N-Substituted (2,3-Dihydro-1,4-benzodioxin-2-yl)methylamine Derivatives as D₂ Antagonists/5-HT_1A Partial Agonists with Potential as Atypical Antipsychotic Agents

  摘要：

  A series of N-substituted 1-(2,3-dihydro-1,4-benzodioxin-2-yl)methylamine derivatives with D-2 antagonist/5-HT1A partial agonist activity has been prepared as potential atypical antipsychotic agents. Optimization of in vitro receptor binding activity and in vivo activity in rodent models of psychosis has led to compound 24, which showed good affinities for human D-2, D-3, and 5-HT1A receptors but significantly less affinity for human alpha(1) adrenoceptors and rat H-1 and muscarinic receptors. In rodents, 24 showed functional D-2-like antagonism and 5-HT1A partial agonism. After oral dosing, 24 showed good activity in rodent antipsychotic tests and very little potential to cause extrapyramidal side effects (EPS), as measured by its ability to induce catalepsy in rats only at very high doses. In the light of this promising profile of activity, 24 has been selected for clinical investigation as a novel antipsychotic agent with a predicted low propensity to cause EPS.

  DOI：

  10.1021/jm9910122

文献信息

• [EN] BICYCLIC AROMATIC COMPOUNDS AS THERAPEUTIC AGENTS<br/>[FR] COMPOSES BICYCLIQUES AROMATIQUES UTILISES COMME AGENTS THERAPEUTIQUES
  申请人：KNOLL AG

  公开号：WO1995007274A1

  公开（公告）日：1995-03-16

  (EN) Compounds of formula (I) and pharmaceutically acceptable salts thereof in which A is methylene or -O-; B is methylene or -O-; and g is 0, 1, 2, 3 or 4; U is an alkylene chain optionally substitued by one or more alkyl; Q represents a divalent group containing nitrogen atoms; having utility in the treatment of central nervous system disorders, for example depression, anxiety, psychoses (for example schizophrenia), tardive dyskinesia, Parkinson's disease, obesity, hypertension, Tourette's syndrome, sexual dysfunction, drug addiction, drug abuse, cognitive disorders, Alzheimer's disease, senile dementia, obsessive-compulsive behaviour, panic attacks, eating disorders and anorexia, cardiovascular and cerebrovascular disorders, non-insulin dependent diabetes mellitus, hyperglycaemia, constipation, arrhythmia, disorders of the neuroendocrine system, stress, prostatic hypertrophy, and spasticity.(FR) Composés de la formule (I) et sels pharmaceutiquement acceptables de ces composés; formule dans laquelle A représente méthylène ou -O-; B représente méthylène ou -O-; et g vaut 0, 1, 2, 3, ou 4; U représente une chaîne alkylène éventuellement substituée par au moins un alkyle; et Q représente un groupe bivalent contenant des atomes d'azote. Ces composés conviennent au traitement de troubles du système nerveux central, tels que la dépression, l'anxiété, les psychoses (la schizophrénie, notamment), la dyskinésie tardive, la maladie de Parkinson, l'obésité, l'hypertension, le syndrome de Tourette, le dysfonctionnement sexuel, la toxicomanie, l'abus des drogues, les troubles cognitifs, la maladie d'Alzheimer, la démence sénile, les névroses obsessionnelles, les crises de panique, les troubles alimentaires et l'anorexie, les affections cardiovasculaires et cérébrovasculaires, le diabète sucré non insulino-dépendant, l'hyperglycémie, la constipation, l'arythmie cardiaque, les troubles du système endocrinien, le stress, l'hypertrophie prostatique et la spasmodicité.

  化合物的化学式为(I)，其药物可接受的盐包括：其中A为亚甲基或-O-；B为亚甲基或-O-；g为0、1、2、3或4；U为一种可以被一个或多个烷基取代的烷基链；Q代表含有氮原子的二价基团。这些化合物适用于治疗中枢神经系统疾病，例如抑郁症、焦虑症、精神病（例如精神分裂症）、迟发性运动障碍、帕金森病、肥胖症、高血压、杜雷特综合征、性功能障碍、药物成瘾、药物滥用、认知障碍、阿尔茨海默病、老年性痴呆、强迫症、惊恐发作、进食障碍和厌食症、心血管和脑血管疾病、非胰岛素依赖型糖尿病、高血糖、便秘、心律失常、神经内分泌系统疾病、压力、前列腺肥大和痉挛症。
• BICYCLIC AROMATIC COMPOUNDS AS THERAPEUTIC AGENTS
  申请人：Knoll AG

  公开号：EP0717739A1

  公开（公告）日：1996-06-26
• 1,4-Benzodioxane derivatives having affinity for D2 receptors and utility in the treatment of psychoses
  申请人：Knoll AG

  公开号：EP0717739B1

  公开（公告）日：2000-03-29
• US5767116A
  申请人：——

  公开号：US5767116A

  公开（公告）日：1998-06-16
• <i>N</i>-Substituted (2,3-Dihydro-1,4-benzodioxin-2-yl)methylamine Derivatives as D₂ Antagonists/5-HT_1A Partial Agonists with Potential as Atypical Antipsychotic Agents
  作者：Alan M. Birch、Paul A. Bradley、Julie C. Gill、Frank Kerrigan、Pat L. Needham

  DOI：10.1021/jm9910122

  日期：1999.8.1

  A series of N-substituted 1-(2,3-dihydro-1,4-benzodioxin-2-yl)methylamine derivatives with D-2 antagonist/5-HT1A partial agonist activity has been prepared as potential atypical antipsychotic agents. Optimization of in vitro receptor binding activity and in vivo activity in rodent models of psychosis has led to compound 24, which showed good affinities for human D-2, D-3, and 5-HT1A receptors but significantly less affinity for human alpha(1) adrenoceptors and rat H-1 and muscarinic receptors. In rodents, 24 showed functional D-2-like antagonism and 5-HT1A partial agonism. After oral dosing, 24 showed good activity in rodent antipsychotic tests and very little potential to cause extrapyramidal side effects (EPS), as measured by its ability to induce catalepsy in rats only at very high doses. In the light of this promising profile of activity, 24 has been selected for clinical investigation as a novel antipsychotic agent with a predicted low propensity to cause EPS.