BTS 79018 | 246517-66-8

• 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: BTS 79018
• 英文别名: 4-Piperidinemethanamine, N-(((2S)-7-chloro-2,3-dihydro-1,4-benzodioxin-2-yl)methyl)-1-(2-methoxyphenyl)-；N-[[(3S)-6-chloro-2,3-dihydro-1,4-benzodioxin-3-yl]methyl]-1-[1-(2-methoxyphenyl)piperidin-4-yl]methanamine
• CAS: 246517-66-8
• 化学式: C₂₂H₂₇ClN₂O₃
• 分子量: 402.921
• InChiKey: QHLRKDSRGUZHSH-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  43
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 BTS 79018 以 甲醇 为溶剂， 反应 48.0h， 以to give a (S)-(−)-2-{4-[N-tert-butoxycarbonyl-N-(7-chloro-2,3-dihydro-1,4-benzodioxin-2-ylmethyl)-aminomethyl]piperidino}phenol as a yellow oil的产率得到(S)-(-)-2-{4-[N-tert-butoxycarbonyl-N-(7-chloro-2,3-dihydro-1,4-benzodioxin-2-ylmethyl)-aminomethyl]piperidino}phenol
  参考文献：
  名称：

  Therapeutic agents

  摘要：

  描述了化合物(I)的复合物，包括其药学上可接受的盐，其中R1代表卤素或假卤素，R2代表来自C7-C18饱和脂肪族羧酸的酰基或氢原子；但是当R1为Cl或CF3且R2为H时，这些化合物为孤立形式，其制备和在治疗抑郁症、焦虑症、精神病、帕金森病、肥胖症、高血压、图雷特综合症、性功能障碍、药物成瘾、药物滥用、认知障碍、阿尔茨海默病、老年痴呆症、强迫症状、惊恐发作、进食障碍、厌食症、心血管和脑血管疾病、非胰岛素依赖性糖尿病、高血糖、便秘、心律失常、神经内分泌系统疾病、应激、前列腺肥大、药物诱导的锥体外系症状或痉挛方面的用途。

  公开号：

  US20040039023A1
• 作为产物：
  描述：

  4-吡啶甲酰胺 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 乙腈 为溶剂， 反应 124.0h， 生成 BTS 79018
  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

• J. Med. Chem. 1999, 42, 3342-3355
  作者：

  DOI：——

  日期：——
• <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.
• Therapeutic agents
  申请人：——

  公开号：US20040039023A1

  公开（公告）日：2004-02-26

  Compound of formula (I) including pharmaceutically acceptable salts thereof in which R 1 represents halo or pseudohalo and R 2 represents H or an acyl group derived from a C 7 -C 18 saturated aliphatic carboxylic acid; with the proviso that when R 1 is Cl or CF 3 and R 2 is H then these compounds are in isolated form, their preparation and their use in the treatment of depression, anxiety, psychoses, Parkison'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, anorexia, cardiovascular and cerebrovascular disorders, non-insulin dependent diabetes mellitus, hyperglycaemia, constipation, arrhythmia, disorders of the neuroendocrine system, stress, prostatic hypertrophy, drug-induced extrapyramidal symptoms or spasticity; are described. 1

  描述了化合物(I)的复合物，包括其药学上可接受的盐，其中R1代表卤素或假卤素，R2代表来自C7-C18饱和脂肪族羧酸的酰基或氢原子；但是当R1为Cl或CF3且R2为H时，这些化合物为孤立形式，其制备和在治疗抑郁症、焦虑症、精神病、帕金森病、肥胖症、高血压、图雷特综合症、性功能障碍、药物成瘾、药物滥用、认知障碍、阿尔茨海默病、老年痴呆症、强迫症状、惊恐发作、进食障碍、厌食症、心血管和脑血管疾病、非胰岛素依赖性糖尿病、高血糖、便秘、心律失常、神经内分泌系统疾病、应激、前列腺肥大、药物诱导的锥体外系症状或痉挛方面的用途。