N,N'-dimethyl-5-nitrobenzene-1,3-dicarboxamide | 349408-79-3

• 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: N,N'-dimethyl-5-nitrobenzene-1,3-dicarboxamide
• 英文别名: 1-N,3-N-dimethyl-5-nitrobenzene-1,3-dicarboxamide
• CAS: 349408-79-3
• 化学式: C₁₀H₁₁N₃O₄
• 分子量: 237.215
• InChiKey: RAGKIDSNQXYOEU-UHFFFAOYSA-N

物化性质

• 沸点：
  447.7±40.0 °C(Predicted)
• 密度：
  1.303±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N'-dimethyl-5-nitrobenzene-1,3-dicarboxamide 在 palladium on activated charcoal sodium azide 、 氢气 、 trifluoromethanesulfonic acid anhydride 作用下， 以 甲醇 、 乙酸乙酯 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Discovery of CC Chemokine Receptor-3 (CCR3) Antagonists with Picomolar Potency

  摘要：

  Starting with our previously described(20) class of CC chemokine receptor-3 (CCR3) antagonist, we improved the potency by replacing the phenyl linker of 1 with a cyclohexyl linker and by replacing the 4-benzylpiperidine with a 3-benzylpiperidine. The resulting compound, 32, is a potent and selective antagonist of CCR3. SAR studies showed that the 3-acetylphenyl urea of 32 could be replaced with heterocyclic ureas or heterocyclic-substituted phenyl ureas and still maintain the potency (inhibition of eotaxin-induced chemotaxis) of this class of compounds in the low-picomolar range (IC50 = 10-60 pM), representing some of the most potent CCR3 antagonists reported to date. The potency of 32 for mouse CCR3 (chemotaxis IC50 = 41 nM) and its oral bioavailability in mice (20% F) were adequate to assess the efficacy in animal models of allergic airway inflammation. Oral administration of 32 reduced eosinophil recruitment into the lungs in a dose-dependent manner in these animal models. On the basis of its overall potency, selectivity, efficacy, and safety profile, the benzenesulfonate salt of 32, designated DPC168, entered phase 1 clinical trials.

  DOI：

  10.1021/jm049530m
• 作为产物：
  描述：

  5-硝基异酞酰氯 、 甲胺 以 四氢呋喃 为溶剂， 生成 N,N'-dimethyl-5-nitrobenzene-1,3-dicarboxamide
  参考文献：
  名称：

  SUBSTITUTED PIPERIDINES AS CCR3 ANTAGONISTS

  摘要：

  本发明的对象是公式1的新型取代化合物，其中A、R1、R2、R3和R4的定义如描述中所述。本发明的另一个对象是提供CCR3的拮抗剂，更具体地提供包含药用可接受载体和本发明化合物中至少一种或其药用可接受盐的治疗有效量的药物组合物。

  公开号：

  US20100261687A1

文献信息

• SUBSTITUTED PIPERIDINES AS CCR3 ANTAGONISTS
  申请人：GRUNDL Marc

  公开号：US20100261687A1

  公开（公告）日：2010-10-14

  Object of the present invention are novel substituted compounds of the formula 1, wherein A, R 1 , R 2 , R 3 and R 4 are defined as in the description. Another object of the present invention is to provide antagonists of CCR3, more particularly to provide pharmaceutical compositions comprising a pharmaceutically acceptable carrier and a therapeutically effective amount of at least one of the compounds of the present invention or a pharmaceutically acceptable salt thereof.

  本发明的对象是公式1的新型取代化合物，其中A、R1、R2、R3和R4的定义如描述中所述。本发明的另一个对象是提供CCR3的拮抗剂，更具体地提供包含药用可接受载体和本发明化合物中至少一种或其药用可接受盐的治疗有效量的药物组合物。
• Resin compositions
  申请人：Schmidt Hans-Werner

  公开号：US20070149663A1

  公开（公告）日：2007-06-28

  A composition containing a) a natural or synthetic polymer and b) one or more compounds of the formula (I), (II) or (III) wherein R 1 , R 2 and R 3 or Y 1 , Y 2 and Y 3 or Z 1 , Z 2 and Z 3 are e.g. branched C 3 -C 20 alkyl.

  一种组合物，包含a) 天然或合成聚合物和b) 一个或多个符合公式(I)，(II)或(III)的化合物，其中R1，R2和R3或Y1，Y2和Y3或Z1，Z2和Z3为分支的C3-C20烷基。
• Therapeutic methods employing substituted piperidines which are CCR3 antagonists
  申请人：GRUNDL Marc

  公开号：US20130023517A1

  公开（公告）日：2013-01-24

  Object of the present invention are novel substituted compounds of the formula 1, wherein A, R 1 , R 2 , R 3 and R 4 are defined as in the description. Another object of the present invention is to provide antagonists of CCR3, more particularly to provide pharmaceutical compositions comprising a pharmaceutically acceptable carrier and a therapeutically effective amount of at least one of the compounds of the present invention or a pharmaceutically acceptable salt thereof.

  本发明的目的是提供公式1的新型取代化合物，其中A、R1、R2、R3和R4的定义如描述中所述。本发明的另一个目的是提供CCR3的拮抗剂，更具体地提供包含药学上可接受的载体和本发明化合物中至少一种或其药学上可接受的盐的治疗有效量的制药组合物。
• US7790793B2
  申请人：——

  公开号：US7790793B2

  公开（公告）日：2010-09-07
• US8278302B2
  申请人：——

  公开号：US8278302B2

  公开（公告）日：2012-10-02