4-hydroxy-3-{[1-(trans-1-methyl-4-{[2-(methyloxy)ethyl]oxy}cyclohexyl)-4-piperidinyl]amino}benzonitrile | 1134197-57-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-hydroxy-3-{[1-(trans-1-methyl-4-{[2-(methyloxy)ethyl]oxy}cyclohexyl)-4-piperidinyl]amino}benzonitrile
• CAS: 1134197-57-1
• 化学式: C₂₂H₃₃N₃O₃
• 分子量: 387.522
• InChiKey: KWVMTLJYBCWMBO-XYWHTSSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  28.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  77.75
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-hydroxy-3-{[1-(trans-1-methyl-4-{[2-(methyloxy)ethyl]oxy}cyclohexyl)-4-piperidinyl]amino}benzonitrile 在 N,N-二异丙基乙胺 、 N,N'-羰基二咪唑 作用下， 以 二氯甲烷 为溶剂， 生成 3-[1-(trans-1-methyl-4-{[2-(methyloxy)ethyl]oxy}cyclohexyl)-4-piperidinyl]-2-oxo-2,3-dihydro-1,3-benzoxazole-5-carbonitrile
  参考文献：
  名称：

  The discovery of a series of N-substituted 3-(4-piperidinyl)-1,3-benzoxazolinones and oxindoles as highly brain penetrant, selective muscarinic M1 agonists

  摘要：

  A series of N-substituted 3-(4-piperidinyl)-1,3-benzoxazolinones and oxindoles are reported which were found to be potent and selective muscarinic M-1 agonists. By control of the physicochemical characteristics of the series, particularly the lipophilicity, compounds with good metabolic stability and excellent brain penetration were identified. An exemplar of the series was shown to be pro-cognitive in the novel object recognition rat model of temporal induced memory deficit. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.07.097
• 作为产物：
  描述：

  3-{[1-(trans-1-methyl-4-{[2-(methyloxy)ethyl]oxy}cyclohexyl)-4-piperidinyl]amino}-4-[(phenylmethyl)oxy]benzonitrile 在 palladium 10% on activated carbon 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 15.0h， 以88%的产率得到4-hydroxy-3-{[1-(trans-1-methyl-4-{[2-(methyloxy)ethyl]oxy}cyclohexyl)-4-piperidinyl]amino}benzonitrile
  参考文献：
  名称：

  [EN] COMPOUNDS WHICH HAVE ACTIVITY AT M1 RECEPTOR AND THEIR USES IN MEDICINE
  [FR] COMPOSÉS PRÉSENTANT UNE ACTIVITÉ AU NIVEAU DU RÉCEPTEUR M1 ET LEURS UTILISATIONS EN MÉDECINE

  摘要：

  提供具有公式(I)或其盐的化合物：其中R4、R5、R6、Q、A、Y和R按描述定义。披露了这些化合物作为药物的使用和在制造用于治疗精神病性障碍、认知障碍和阿尔茨海默病药物中的应用。本发明还公开了包含这些化合物的药物组合物。

  公开号：

  WO2009037294A1

文献信息

• Compounds which have activity at M1 receptor and their uses in medicine
  申请人：Cooper David Gwyn

  公开号：US20100204272A1

  公开（公告）日：2010-08-12

  Compounds of formula (I) or a salt thereof are provided: wherein R 4 , R 5 , R 6 , Q, A, Y and R are as defined in the description. Uses of the compounds as medicaments and in the manufacture of medicaments for treating psychotic disorders, cognitive impairments and Alzheimer's Disease are disclosed. The invention further discloses pharmaceutical compositions comprising the compounds.

  本发明提供了化学式(I)的化合物或其盐：其中R4，R5，R6，Q，A，Y和R的定义如说明书中所定义。本发明还揭示了将该化合物用作药物以及制造用于治疗精神障碍，认知障碍和阿尔茨海默病的药物的用途。本发明还揭示了包含该化合物的制药组合物。
• Compounds Which Have Activity at M1 Receptor and Their Uses in Medicine
  申请人：Cooper David Gwyn

  公开号：US20120316196A1

  公开（公告）日：2012-12-13

  Compounds of formula (I) or a salt thereof are provided: wherein R 4 , R 5 , R 6 , Q, A, Y and R are as defined in the description. Uses of the compounds as medicaments and in the manufacture of medicaments for treating psychotic disorders, cognitive impairments and Alzheimer's Disease are disclosed. The invention further discloses pharmaceutical compositions comprising the compounds.

  提供化学式(I)的化合物或其盐： 其中R4、R5、R6、Q、A、Y和R的定义如说明书所述。本发明还公开了将该化合物用作药物治疗精神疾病、认知障碍和阿尔茨海默病以及制造药物的用途。本发明还公开了包含该化合物的制药组合物。
• COMPOUNDS WHICH HAVE ACTIVITY AT M1 RECEPTOR AND THEIR USES IN MEDICINE
  申请人：Glaxo Group Limited

  公开号：EP2194982A1

  公开（公告）日：2010-06-16
• US8278328B2
  申请人：——

  公开号：US8278328B2

  公开（公告）日：2012-10-02
• US8299257B2
  申请人：——

  公开号：US8299257B2

  公开（公告）日：2012-10-30