5-amino-4-(4-methoxy-2,6-dimethylphenyl)-3-methylpyrazole | 332179-71-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-amino-4-(4-methoxy-2,6-dimethylphenyl)-3-methylpyrazole
• 英文别名: 4-(4-methoxy-2,6-dimethylphenyl)-5-methyl-1H-pyrazol-3-amine
• CAS: 332179-71-2
• 化学式: C₁₃H₁₇N₃O
• 分子量: 231.297
• InChiKey: OKUQOTYPNHQPES-UHFFFAOYSA-N

物化性质

• 沸点：
  391.1±42.0 °C(Predicted)
• 密度：
  1.148±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  63.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-amino-4-(4-methoxy-2,6-dimethylphenyl)-3-methylpyrazole 在 溶剂黄146 、 N,N-二乙基苯胺 、 三氯氧磷 作用下， 以 异丙醇 、 甲苯 为溶剂， 反应 12.0h， 生成 N-(1-ethylpropyl)-3-(4-methoxy-2,6-dimethylphenyl)-2-methyl-6,7-dihydro-5H-cyclopenta[d]pyrazolo[1,5-a]pyrimidin-8-amine
  参考文献：
  名称：

  6,7-Dihydro-5H-cyclopenta[d]pyrazolo[1,5-a]pyrimidines and their derivatives as novel corticotropin-releasing factor 1 receptor antagonists

  摘要：

  To identify an orally active corticotropin-releasing factor 1 receptor antagonist, a series of 6,7-dihydro-5H-cyclopenta[d]pyrazolo[1,5-a]pyrimidines and their derivatives were designed, synthesized and evaluated. An in vitro study followed by in vivo and pharmacokinetic studies of these heterotricyclic compounds led us to the discovery of an orally active CRF1 receptor antagonist. The results of a structure-activity relationship study are presented. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.055
• 作为产物：
  描述：

  2-(4-Methoxy-2,6-dimethylphenyl)-3-oxobutanenitrile 在 一水合肼 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 18.0h， 生成 5-amino-4-(4-methoxy-2,6-dimethylphenyl)-3-methylpyrazole
  参考文献：
  名称：

  8-(4-Methoxyphenyl)pyrazolo[1,5-a]-1,3,5-triazines: Selective and Centrally Active Corticotropin-Releasing Factor Receptor-1 (CRF₁) Antagonists

  摘要：

  This report describes the syntheses and structure-activity relationships of 8-(4-methoxyphenyl)pyrazolo[1,5-a]-1,3,5-triazine corticotropin releasing factor receptor-1 (CRF1) receptor antagonists. CRF1 receptor antagonists may be potential anxiolytic or antidepressant drugs. This research culminated in the discovery of analogue 12-3. which is a potent, selective CRF1 antagonist (hCRF(1) IC50 = 4.7 +/- 2.0 nM) with weak affinity for the CRF-binding protein and biogenic amine receptors. This compound also has a good pharmacokinetic profile in dogs. Analogue 12-3 is orally effective in two rat models of anxiety: the defensive withdrawal (situational anxiety) model and the elevated plus maze test. Analogue 12-3 has been advanced to clinical trials.

  DOI：

  10.1021/jm9000242

文献信息

• Certain alkylene diamine-substituted pyrazlo (1,5-a)-1,5-pyrimidines and pyrazolo (1,5-a) 1,3,5-triazines
  申请人：Neurogen Corporation

  公开号：US06372743B1

  公开（公告）日：2002-04-16

  Disclosed are compounds of the formula: where R1, R2, R3, R4, R5, R6, and X are defined herein. These compounds are selective modulators of NPY1 receptors. These compounds are useful in the treatment of a number of CNS disorders, metabolic disorders, and peripheral disorders, particularly eating disorders and hypertension. Methods of treatment of such disorders and well as packaged pharmaceutical compositions are also provided. Compounds of the invention are also useful as probes for the localization of NPY1 receptors and as standards in assays for NPY1 receptor binding. Methods of using the compounds in receptor localization studies are given.

  揭示了以下化合物的结构：其中R1、R2、R3、R4、R5、R6和X的定义如下。这些化合物是NPY1受体的选择性调节剂。这些化合物在治疗多种中枢神经系统疾病、代谢性疾病和外周疾病方面具有用途，尤其是在治疗进食障碍和高血压方面。还提供了治疗此类疾病的方法以及包装的药物组合。发明的化合物还可用作NPY1受体定位的探针和NPY1受体结合测定中的标准。给出了使用这些化合物进行受体定位研究的方法。
• Amino substituted pyrazolo[1,5,-a]-1,5-pyrimidines and pyrazolo[1,5-a]-1,3,5-triazines
  申请人：Neurogen Corporation

  公开号：US06476038B1

  公开（公告）日：2002-11-05

  Disclosed are compounds of the formula: where R1, R2, R3, R4, R5, R6, and X are defined herein. These compounds are selective modulators of NPY1 receptors. These compounds are useful in the treatment of a number of CNS disorders, metabolic disorders, and peripheral disorders, particularly eating disorders and hypertension. Methods of treatment of such disorders and well as packaged pharmaceutical compositions are also provided. Compounds of the invention are also useful as probes for the localization of NPY1 receptors and as standards in assays for NPY1 receptor binding. Methods of using the compounds in receptor localization studies are given.

  揭示了以下公式的化合物：其中R1、R2、R3、R4、R5、R6和X在此处定义。这些化合物是NPY1受体的选择性调节剂。这些化合物在治疗许多中枢神经系统疾病、代谢性疾病和外周疾病方面具有用途，尤其是在治疗进食障碍和高血压方面。还提供了治疗这些疾病的方法以及包装的药物组合物。发明的化合物还可用作NPY1受体定位的探针，以及NPY1受体结合测定的标准。给出了在受体定位研究中使用这些化合物的方法。
• Certain alkylene diamine-substituted pyrazolo[1,5,-a]-1,5-pyrimidines and pyrazolo [1,5-a]-1,3,5-triazines
  申请人：Neurogen Corporation

  公开号：US20030069246A1

  公开（公告）日：2003-04-10

  Disclosed are compounds of the formula: 1 where R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and X are defined herein. These compounds are selective modulators of NPY1 receptors. These compounds are useful in the treatment of a number of CNS disorders, metabolic disorders, and peripheral disorders, particularly eating disorders and hypertension. Methods of treatment of such disorders and well as packaged pharmaceutical compositions are also provided. Compounds of the invention are also useful as probes for the localization of NPY1 receptors and as standards in assays for NPY1 receptor binding. Methods of using the compounds in receptor localization studies are given.

  本发明揭示了以下化合物的公式：1其中R1、R2、R3、R4、R5、R6和X在此定义。这些化合物是NPY1受体的选择性调节剂。这些化合物在治疗许多中枢神经系统疾病、代谢性疾病和外周疾病，特别是进食障碍和高血压方面非常有用。本发明还提供了治疗这些疾病的方法以及包装的制药组合物。本发明的化合物还可用作NPY1受体定位的探针，以及在NPY1受体结合测定中的标准。给出了在受体定位研究中使用这些化合物的方法。
• CERTAIN ALKYLENE DIAMINE-SUBSTITUTED PYRAZOLO 1,5,-a]-1,5-PYRIMIDINES AND PYRAZOLO 1,5-a]-1,3,5-TRIAZINES
  申请人：NEUROGEN CORPORATION

  公开号：EP1218379A2

  公开（公告）日：2002-07-03
• AMINO SUBSTITUTED PYRAZOLO 1,5,-a]-1,5-PYRIMIDINES AND PYRAZOLO 1,5-a]-1,3,5-TRIAZINES
  申请人：NEUROGEN CORPORATION

  公开号：EP1218381A2

  公开（公告）日：2002-07-03