3-(3-pyrrolidinyloxy)-pyridine | 224818-27-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(3-pyrrolidinyloxy)-pyridine
• 英文别名: 3-(Pyrrolidin-3-yloxy)pyridine；3-pyrrolidin-3-yloxypyridine
• CAS: 224818-27-3
• 化学式: C₉H₁₂N₂O
• mdl: MFCD08688535
• 分子量: 164.207
• InChiKey: DCWKRPJLVIHGCZ-UHFFFAOYSA-N

物化性质

• 沸点：
  284.9±30.0 °C(Predicted)
• 密度：
  1.113±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.444
• 拓扑面积：
  34.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (+/-)-3-oxy(3-pyridyl)-1-tert-butoxycarbonylpyrrolidine 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以30.4%的产率得到3-(3-pyrrolidinyloxy)-pyridine
  参考文献：
  名称：

  烟碱乙酰胆碱受体的新型吡啶醚的合成及其构效关系

  摘要：

  描述了新型吡啶基醚作为烟碱乙酰胆碱受体（nAChR）配体的制备。氮杂环的环大小的变化和吡啶上的取代对α4beta2nAChR处IC50的受体结合亲和力具有显着影响，范围为22至> 10,000 nM。最有效的分子是（R）-2-氯-3-（4-氰基苯基）-5-（（3-吡咯烷基）氧基）吡啶27f，IC50为22 nM。

  DOI：

  10.1016/s0960-894x(00)00168-2

文献信息

• POSITIVE ALLOSTERIC MODULATORS OF THE MUSCARINIC ACETYLCHOLINE RECEPTOR M4
  申请人：Vanderbilt University

  公开号：US20170369505A1

  公开（公告）日：2017-12-28

  Disclosed herein are tricyclic compounds, including pyrimido[4′,5′:4,5]thieno[2,3-c]pyridazine-8-amine, pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidine-4-amine, pyrazino[2′,3′:4,5]thieno[3,2-d]pyrimidin-4-amine, pyrido[3′,2′:4,5]furo[3, 2-d]pyrimidin-4-amine, and pyrimido[4′,5′:4,5]furo[2,3-c]pyridazin-8-amine compounds, which may be useful as positive allosteric modulators of the muscarinic acetylcholine receptor M 4 (mAChR M 4 ). Also disclosed herein are methods of making the compounds, pharmaceutical compositions comprising the compounds, and methods of treating neurological and psychiatric disorders associated with muscarinic acetylcholine receptor dysfunction using the compounds and compositions.

  本文披露了三环化合物，包括嘧啶并[4′,5′:4,5]噻吩并[2,3-c]吡啶嗪-8-胺，吡啶并[3′,2′:4,5]噻吩并[3,2-d]嘧啶-4-胺，吡嗪并[2′,3′:4,5]噻吩并[3,2-d]嘧啶-4-胺，吡啶并[3′,2′:4,5]呋喃[3,2-d]嘧啶-4-胺，以及嘧啶并[4′,5′:4,5]呋喃[2,3-c]吡啶嗪-8-胺化合物，这些化合物可能作为肌胆碱受体M4（mAChR M4）的正向变构调节剂而有用。本文还披露了制备这些化合物的方法，包括这些化合物的药物组合物，以及使用这些化合物和组合物治疗与肌胆碱受体功能障碍相关的神经和精神疾病的方法。
• Pyridyl ethers and thioethers as ligands for nicotinic acetylcholine receptor and its therapeutic application
  申请人：——

  公开号：US20030207858A1

  公开（公告）日：2003-11-06

  The present invention provides compounds of the formula: 1 wherein m is 0, 1 or 2; p is 0 or 1; Y is O, S, S(O) or S(O) 2 and R 1 to R 7 are various substituents as selective modulators of the nicotinic acetylcholine receptor useful in the treatment of pain, Alzheimer's disease, memory loss or dementia or loss of motor function.

  本发明提供了以下式的化合物： 其中m为0、1或2；p为0或1；Y为O、S、S(O)或S(O)2；R1至R7为各种取代基，作为选择性调节尼古丁乙酰胆碱受体的药物，用于治疗疼痛、阿尔茨海默病、记忆丧失或痴呆症或运动功能丧失。
• PHARMACEUTICAL COMPOSITIONS AND METHODS FOR USE
  申请人：——

  公开号：US20010014691A1

  公开（公告）日：2001-08-16

  Patients susceptible to or suffering from conditions and disorders, such as central nervous system disorders, are treated by administering to a patient in need thereof aryloxyalkylamines, including pyridyloxylalkylamines and phenoxyalkylamines. Exemplary compounds include dimethyl(2-(3-pyridyloxy)ethylamine, dimethyl(4-(3-pyridyloxy)butyl)amine, 2-(3-pyridyloxy)ethylamine, 4-(3-pyridyloxy)butylamine, methyl(3-(5-methoxy-3-pyridyloxy)propyl)amine, ethyl(3-(3-pyridyloxy)propyl)amine, methyl(2-(3-pyridyloxy)ethyl)amine, methyl(3-(6-methyl(3-pyridyloxy))propyl)amine, (3-(3-methoxyphenoxy)propyl)methylamine, (3-(5-chloro(3-pyridyloxy))-1-methylpropyl)methylamine, dimethyl(3-(3-pyridyloxy)propyl)amine, 3-(3-pyridyloxy)propylamine, methyl(4-(3-pyridyloxy)butyl)amine, 3-(5-chloro-3-pyridyloxy)propyl amine, methyl(3-(5-isopropoxy-3-pyridyloxy)propyl)amine, (3-(5-chloro(3-pyridyloxy))propyl) methylamine, methyl(3-(5-(phenylmethoxy)(3-pyridyloxy))propyl)amine, methyl(3-(2-methyl(3-pyridyloxy))propyl)amine, (methylethyl)(3-(3-pyridyloxy)propyl)amine, benzyl(3-(3-pyridyloxy)propyl)amine, cyclopropyl(3-(3-pyridyloxy)-propyl)amine, methyl(1-methyl-3-(3-pyridyloxy)propyl)amine, methyl(3-(3-nitrophenoxy)propyl)amine, 1-(3-chloropropoxy)-3-nitrobenzene, (3-(3-aminophenoxy)propyl)methylamine,dimethyl (3-(3-(methylamino)-propoxy)phenyl)amine, methyl(3-tricyclo[7.3.1.0<5,13>]tridec-2-yloxypropyl)amine, (3-benzo[3,4-d]1,3-dioxolan-5-yloxypropyl)methylamine, 3-(4-piperidinyloxy)pyridine and 3-((3S)-3-pyrrolidinyloxy)pyridine.

  患有或易受中枢神经系统疾病等病症和紊乱的患者，通过向需要的患者施用芳基氧烷胺类化合物进行治疗，包括吡啶氧烷胺和苯氧烷胺。示例化合物包括二甲基(2-(3-吡啶氧基)乙基)胺，二甲基(4-(3-吡啶氧基)丁基)胺，2-(3-吡啶氧基)乙基胺，4-(3-吡啶氧基)丁基胺，甲基(3-(5-甲氧基-3-吡啶氧基)丙基)胺，乙基(3-(3-吡啶氧基)丙基)胺，甲基(2-(3-吡啶氧基)乙基)胺，甲基(3-(6-甲基(3-吡啶氧基))丙基)胺，(3-(3-甲氧基苯氧基)丙基)甲基胺，(3-(5-氯(3-吡啶氧基))-1-甲基丙基)甲基胺，二甲基(3-(3-吡啶氧基)丙基)胺，3-(3-吡啶氧基)丙基胺，甲基(4-(3-吡啶氧基)丁基)胺，3-(5-氯-3-吡啶氧基)丙基胺，甲基(3-(5-异丙氧基-3-吡啶氧基)丙基)胺，(3-(5-氯(3-吡啶氧基))丙基)甲基胺，甲基(3-(5-(苯甲氧基)(3-吡啶氧基))丙基)胺，甲基(3-(2-甲基(3-吡啶氧基))丙基)胺，(甲基乙基)(3-(3-吡啶氧基)丙基)胺，苄基(3-(3-吡啶氧基)丙基)胺，环丙基(3-(3-吡啶氧基)-丙基)胺，甲基(1-甲基-3-(3-吡啶氧基)丙基)胺，甲基(3-(3-硝基苯氧基)丙基)胺，1-(3-氯丙氧基)-3-硝基苯，(3-(3-氨基苯氧基)丙基)甲基胺，二甲基(3-(3-(甲氨基)-丙氧基)苯基)胺，甲基(3-三环七叁.壹.零<5,13>三十二氧基丙基)胺，(3-苯并三.四-壹,三-二氧杂环戊氧基丙基)甲基胺，3-(4-哌啶氧基)吡啶和3-((3S)-3-吡咯啶氧基)吡啶。
• Synthesis and structure–activity relationship of novel pyridyl ethers for the nicotinic acetylcholine receptor
  作者：Jung Lee、Coralie B. Davis、Ralph A. Rivero、Allen B. Reitz、Richard P. Shank

  DOI：10.1016/s0960-894x(00)00168-2

  日期：2000.5

  The preparation of novel pyridyl ethers as ligands for the nicotinic acetylcholine receptor (nAChR) is described. Variations of the ring size of the azacycle and substitution on the pyridine had dramatic effects on receptor binding affinity with IC50s at the alpha4beta2 nAChR ranging from 22 to >10,000 nM. The most potent molecule was (R)-2-chloro-3-(4-cyanophenyl)-5-((3-pyrrolidinyl)oxy)pyridine 27f

  描述了新型吡啶基醚作为烟碱乙酰胆碱受体（nAChR）配体的制备。氮杂环的环大小的变化和吡啶上的取代对α4beta2nAChR处IC50的受体结合亲和力具有显着影响，范围为22至> 10,000 nM。最有效的分子是（R）-2-氯-3-（4-氰基苯基）-5-（（3-吡咯烷基）氧基）吡啶27f，IC50为22 nM。
• [EN] PYRIDYL ETHERS AND THIOETHERS AS LIGANDS FOR NICOTINIC ACETYLCHOLINE RECEPTOR AND ITS THERAPEUTIC APPLICATION<br/>[FR] PYRIDYL ETHERS ET THIOETHERS TENANT LIEU DE LIGANDS POUR LE RECEPTEUR DE L'ACETYCHOLINE NICOTINIQUE, ET APPLICATION THERAPEUTIQUE
  申请人：ORTHO MCNEIL PHARM INC

  公开号：WO2000010997A1

  公开（公告）日：2000-03-02

  The present invention provides compounds of formula (I) wherein m is 0, 1 or 2; p is 0 or 1; Y is O, S, S(O) or S(O)2 and R1 to R7 are various substituents as selective modulators of the nicotinic acetylcholine receptor useful in the treatment of pain, Alzheimer's disease, memory loss or dementia or loss of motor function.

  本发明提供了式（I）的化合物，其中m为0、1或2；p为0或1；Y为O、S、S（O）或S（O）2，R1至R7为不同的取代基，作为选择性调节剂，对尼古丁乙酰胆碱受体具有有用的治疗作用，可用于疼痛、阿尔茨海默病、记忆丧失或痴呆症或运动功能丧失的治疗。