5-methyl-N-(piperidin-4-yl)-nicotinamide | 916342-93-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5-methyl-N-(piperidin-4-yl)-nicotinamide
• 英文别名: 5-methyl-N-piperidin-4-ylpyridine-3-carboxamide
• CAS: 916342-93-3
• 化学式: C₁₂H₁₇N₃O
• 分子量: 219.286
• InChiKey: VYLFMKUUVMJIPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  54
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-methyl-N-(piperidin-4-yl)-nicotinamide 、 4-氯-3-乙氧基苯甲醛 在 吡啶硼烷 、 溶剂黄146 作用下， 以 吡啶 、 乙醇 、 1,2-二氯乙烷 为溶剂， 反应 16.0h， 以57%的产率得到N-[1-(4-chloro-3-ethoxy-benzyl)piperidin-4-yl]-5-methyl-nicotinamide
  参考文献：
  名称：

  Amide derivatives as somatostatin receptor 5 antagonists

  摘要：

  这项发明涉及以下式中的化合物，其中R1至R5、R5'和A如描述和索赔中所定义，并且其药学上可接受的盐。该发明还涉及含有这种化合物的药物组合物，以及用于治疗和/或预防与调节SST受体亚型5相关的疾病的方法。

  公开号：

  US20060276508A1
• 作为产物：
  描述：

  4-[(5-Methyl-pyridine-3-carbonyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester 反应 2.0h， 以100%的产率得到5-methyl-N-(piperidin-4-yl)-nicotinamide
  参考文献：
  名称：

  Piperidinyl-nicotinamides as potent and selective somatostatin receptor subtype 5 antagonists

  摘要：

  Nicotinamides of benzyl-substituted 4-aminopiperidines and their seven-membered analogs of generic structure 2 and 20 have been discovered as potent and selective SST5 antagonists. The activity (K-i) ranges from 2.4 to 436 nM. Most compounds exhibit decent physicochemical properties and follow a clear SAR pattern. Interestingly enough, the receptor is strongly enantiodiscriminating and binds in the amino-azepaneseries only the (R)-enantiomer. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.06.026

文献信息

• Amide derivatives as somatostatin receptor 5 antagonists
  申请人：Binggeli Alfred

  公开号：US20060276508A1

  公开（公告）日：2006-12-07

  This invention is concerned with compounds of the formula wherein R 1 to R 5 , R 5′ and A are as defined in the description and claims, and pharmaceutically acceptable salts thereof. The invention further relates to pharmaceutical compositions containing such compounds, to a process for their preparation and to their use for the treatment and/or prevention of diseases which are associated with the modulation of SST receptors subtype 5.

  这项发明涉及以下式中的化合物，其中R1至R5、R5'和A如描述和索赔中所定义，并且其药学上可接受的盐。该发明还涉及含有这种化合物的药物组合物，以及用于治疗和/或预防与调节SST受体亚型5相关的疾病的方法。
• From Astemizole to a Novel Hit Series of Small-Molecule Somatostatin 5 Receptor Antagonists via GPCR Affinity Profiling
  作者：Wolfgang Guba、Luke G. Green、Rainer E. Martin、Olivier Roche、Nicole Kratochwil、Harald Mauser、Caterina Bissantz、Andreas Christ、Martin Stahl

  DOI：10.1021/jm701144e

  日期：2007.12.13

  The H1R antagonist astemizole was identified as a somatostatin 5 (SST5) receptor antagonist by a comparative sequence analysis of the consensus drug binding pocket of GPCRs. Subsequently, a similarity analysis of GPCR affinity profiles of astemizole versus a set of in-house GPCR-biased combinatorial libraries revealed new chemical entry points that led to a second lead series with nanomolar binding affinity.
• PIPERIDIN-4-YL-AMIDE DERIVATIVES AND THEIR USE AS SST RECEPTOR SUBTYPE 5 ANTAGONISTS
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP1893603A1

  公开（公告）日：2008-03-05
• US7772253B2
  申请人：——

  公开号：US7772253B2

  公开（公告）日：2010-08-10
• [EN] PIPERIDIN-4-YL-AMIDE DERIVATIVES AND THEIR USE AS SST RECEPTOR SUBTYPE 5 ANTAGONISTS<br/>[FR] DERIVES DE LA PIPERIDIN-4-YL-AMIDE ET LEUR UTILISATION COMME ANTAGONISTES DU SOUS TYPE 5 DU RECEPTEUR SST
  申请人：HOFFMANN LA ROCHE

  公开号：WO2006128803A1

  公开（公告）日：2006-12-07

  [EN] This invention is concerned with compounds of the formula (1) wherein R¹ to R⁵, R^5' and A are as defined in the description and claims, and pharmaceutically acceptable salts thereof. The invention further relates to pharmaceutical compositions containing such compounds, to a process for their preparation and to their use for the treatment and/or prevention of diseases which are associated with the modulation of SST receptors subtype 5.
  [FR] Cette invention concerne les composés de formule (1) dans laquelle R¹ à R⁵, R^5' et A sont tels que définis dans la description et les revendications, et leurs sels acceptables sur un plan pharmaceutique. L'invention concerne de plus des compositions pharmaceutiques contenant de tels composés, un procédé pour leur préparation et leur utilisation pour le traitement et/ou la prévention de maladies qui sont associées à la modulation du sous type 5 des récepteurs SST.