4,4-dimethyl[1,4']bipiperidyl-4'-carboxamide | 1243243-32-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4,4-dimethyl[1,4']bipiperidyl-4'-carboxamide
• 英文别名: 4,4-dimethyl-1,4'-bipiperidinyl-4'-carboxamide；4,4-Dimethyl[1,4'-bipiperidine]-4'-carboxamide；4-(4,4-dimethylpiperidin-1-yl)piperidine-4-carboxamide
• CAS: 1243243-32-4
• 化学式: C₁₃H₂₅N₃O
• 分子量: 239.361
• InChiKey: KLEGHSXEQLBTBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  58.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(4-Chlorophenyl)-4-(2,4-dichlorophenyl)-1-(3-methanesulfonylamino-propyl)-1H-pyrrole-2-carboxylic acid 、 4,4-dimethyl[1,4']bipiperidyl-4'-carboxamide 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1'-[5-(4-chlorophenyl)-4-(2,4-dichlorophenyl)-1-(3-methanesulfonylamino-propyl)-1H-pyrrole-2-carbonyl]-4,4-dimethyl[1,4']bipiperidinyl-4'-carboxamide
  参考文献：
  名称：

  Rational design of a novel peripherally-restricted, orally active CB1 cannabinoid antagonist containing a 2,3-diarylpyrrole motif

  摘要：

  A new series of 2,3-diarylpyrroles have been prepared and evaluated as CB1 antagonists. Modulation of the topological polar surface area allowed the identification of high affinity peripherally-restricted CB1 antagonists. Compound 11, obtained after further optimization of the metabolic profile displayed very low brain penetration, yet was able to reverse CP55940-induced gastrointestinal transit inhibition following oral administration. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.06.017

文献信息

• PYRROLE DERIVATIVES, PREPARATION THEREOF AND THERAPEUTIC USE THEREOF
  申请人：Barth Francis

  公开号：US20090281116A1

  公开（公告）日：2009-11-12

  The invention relates to compounds having the formula (I): Wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 9 and A-R 9 are as defined herein. Also disclosed are the preparative methods for the compounds of formula (I) and their use in therapy.

  这项发明涉及具有以下结构式（I）的化合物：其中R1、R2、R3、R4、R5、R6、R7和R9以及A-R9如本文所定义。还披露了结构式（I）化合物的制备方法以及它们在治疗中的用途。
• DERIVES DE PYRROLE, LEUR PREPARATION ET LEUR UTILISATION EN THERAPEUTIQUE.
  申请人：Sanofi-Aventis

  公开号：EP2094656A2

  公开（公告）日：2009-09-02
• US8044072B2
  申请人：——

  公开号：US8044072B2

  公开（公告）日：2011-10-25
• [EN] P<0}{0PYRROL DERIVATIVES, PREPARATION AND USE OF THE SAME IN THERAPY<0}<br/>[FR] DERIVES DE PYRROLE, LEUR PREPARATION ET LEUR UTILISATION EN THERAPEUTIQUE.
  申请人：SANOFI AVENTIS

  公开号：WO2008068423A2

  公开（公告）日：2008-06-12

  [EN] The invention relates to compounds having the formula (I), wherein A represents: a substituted or non substituted alkylene (C₁-C₆) group; a Formula (II) group having m = O, 1 or 2 and p = 0 or 1; R1 represents hydrogen or a (C₁ -C₂ )alkyl; R2 represents a substituted or non substituted (C3-C10) alkyl group, a substituted or non substituted non aromatic (C₃-C₁₂) carbocylic radical, a heterocyclic substituted or non substituted radical, an alkylene (C₁-C₃) substituted group, a NR₁₀R₁₁ group; R₉ represents a functional group or a heterocyclic radical. Preparation method and use in therapy.<0}
  [FR] L'invention a pour objet des composés répondant à la formule (I) dans laquelle : A représente :. un groupe alkylène en (C₁-C₆) non substitué ou substitué; un groupe Formule (II) avec m = O, 1 ou 2 et p = 0 ou 1; R1 représente l'hydrogène ou un (C₁ -C₂ )alkyle; R2 représente :. un groupe (C3-C10)alkyle non substitué ou substitué;. un radical carbocyclique non aromatique en C₃-C₁₂) non substitué ou substitué;. un radical hétérocyclique non substitué ou substitué;. un groupe (C₁-C₃)alkylène substitué;. un groupement NR₁₀R₁₁; R₉ représente un groupe fonctionnel ou un radical hétérocyclique; Procédé de préparation et application en thérapeutique.
• Rational design of a novel peripherally-restricted, orally active CB1 cannabinoid antagonist containing a 2,3-diarylpyrrole motif
  作者：Laurent Hortala、Murielle Rinaldi-Carmona、Christian Congy、Laurent Boulu、Freddy Sadoun、Gérard Fabre、Olivier Finance、Francis Barth

  DOI：10.1016/j.bmcl.2010.06.017

  日期：2010.8

  A new series of 2,3-diarylpyrroles have been prepared and evaluated as CB1 antagonists. Modulation of the topological polar surface area allowed the identification of high affinity peripherally-restricted CB1 antagonists. Compound 11, obtained after further optimization of the metabolic profile displayed very low brain penetration, yet was able to reverse CP55940-induced gastrointestinal transit inhibition following oral administration. (C) 2010 Elsevier Ltd. All rights reserved.