3-(2,4-dichlorophenyl)-1H-pyrazol-5-amine | 502132-96-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(2,4-dichlorophenyl)-1H-pyrazol-5-amine
• 英文别名: 5-(2,4-dichlorophenyl)-1H-pyrazol-3-amine
• CAS: 502132-96-9
• 化学式: C₉H₇Cl₂N₃
• mdl: MFCD02664282
• 分子量: 228.081
• InChiKey: XSHXVQWCAGNATP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.7
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(2,4-dichlorophenyl)-1H-pyrazol-5-amine 在 水 、 potassium carbonate 、 溶剂黄146 、 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 35.17h， 生成 N-(1-adamantyl)-2-(2,4-dichlorophenyl)-7-oxo-4-pentylpyrazolo[1,5-a]pyrimidine-6-carboxamide
  参考文献：
  名称：

  Discovery of 7-Oxopyrazolo[1,5-a]pyrimidine-6-carboxamides as Potent and Selective CB₂ Cannabinoid Receptor Inverse Agonists

  摘要：

  We recently described the medicinal chemistry of a new series of heteroaryl-4-oxopyridine/7-oxopyrimidines as CB2 receptor partial agonists, showing that the functionality of these ligands is controlled by the nature of the heteroaryl function condensed with the pyridine ring. We describe herein the design and synthesis of the 7-oxopyrazolo[1,5-a]pyrimidine-6-carboxamides, structural isomers of our previously reported pyrazolo[3,4-Hpyridines. All of the new compounds showed high affinity and selectivity for the CB2 receptor in the nanomolar range. In 3,5-cyclic adenosine monophosphate (cAMP) assays, the novel series shows stimulatory effects on forskolin-induced cAMP production acting as inverse agonists.

  DOI：

  10.1021/jm400182t

文献信息

• 5-Acylamino-pyrazol-Derivate
  申请人：BAYER AG

  公开号：EP0269839A1

  公开（公告）日：1988-06-08

  Die Erfindung betrifft neue 5-Acylamino-pyrazol-Derivate der Formel (I) in welcher R1 für Wasserstoff. Halogen oder Nitro steht, R2 für Wasserstoff. Alkyl. Alkenyl. Alkinyl oder gegebenenfall substituiertes Cycloalkyl steht. R3 für Wasserstoff. Alkyl, für gegebenenfalls substituiertes Cycloalkyl-oder für gegebenenfalls substituiertes Aryl steht. Ar für jeweils gegebenenfalls substituiertes Phenyl oder Pyridyl steht, X' für Sauerstoff oder Schwefel steht, A für eine geradkettige oder verzweigte. gegebenenfalls substituierte Alkylenbrücke steht, n für die Zahlen 0 oder 1 steht und X2 für Sauerstoff. für einen Rest = N-O-R4 oder für einen Rest steht, und R4 , R5, und R6 die in der Beschreibung angegebene Bedeutung haben, mehrere Verfahren zu ihrer Herstellung sowie ihre Verwendung als Herbizide und Wachstumsregulatoren.

  本发明涉及式（I）的新 5-酰氨基吡唑衍生物，其中 R1 是氢、卤素或硝基，R2 是氢、烷基、烯基、炔基或任选取代的环烷基，R3 是氢、烷基、任选取代的环烷基或任选取代的芳基，Ar 是任选取代的苯基或吡啶基，X'是氧或硫，A 是直链或支链任选取代的亚烷基桥，n 是数字 0 或 1，X2 是氧、自由基 = N-O-R4 或自由基，R4、R5 和 R6 具有描述中给出的含义，本发明还涉及其制备的多种工艺及其作为除草剂和生长调节剂的用途。
• Pharmacologically active aryl-substituted pyrazolo[1,5-a]pyrimidine derivatives
  申请人：RICHTER GEDEON NYRT.

  公开号：US10960007B2

  公开（公告）日：2021-03-30

  The present invention relates to new pyrazolo[1,5-a]pyrimidine derivatives of formula (I) or pharmaceutically acceptable salts, biologically active metabolites, pro-drugs, racemates, enantiomers, diastereomers, solvates and hydrates thereof that serve as GABAB receptor positive allosteric modulators. The invention also relates to the process for producing such compounds. The invention further relates to pharmaceutical compositions comprising such compounds optionally in combination with two or more different therapeutic agents and the use of such compounds in methods for treating diseases and conditions mediated and modulated by the GABAB receptor positive allosteric mechanism. The invention also provides a method for manufacture of medicaments useful in the treatment of such disorders.

  本发明涉及新的式（I）吡唑并[1,5-a]嘧啶衍生物或其药学上可接受的盐、生物活性代谢物、原药、外消旋体、对映体、非对映异构体、溶液和水合物，可作为 GABAB 受体正异位调节剂。本发明还涉及生产此类化合物的工艺。本发明进一步涉及包含此类化合物的药物组合物（可选择与两种或两种以上不同的治疗剂组合），以及此类化合物在治疗由 GABAB 受体正性异位调节机制介导和调节的疾病和病症的方法中的用途。本发明还提供了一种用于治疗此类疾病的药物的制造方法。
• Pharmacologically Active Aryl-Substituted Pyrazolo[1,5-a]Pyrimidine Derivatives
  申请人：RICHTER GEDEON NYRT.

  公开号：US20200061068A1

  公开（公告）日：2020-02-27

  The present invention relates to new pyrazolo[1,5-a]pyrimidine derivatives of formula (I) or pharmaceutically acceptable salts, biologically active metabolites, pro-drugs, racemates, enantiomers, diastereomers, solvates and hydrates thereof that serve as GABA B receptor positive allosteric modulators. The invention also relates to the process for producing such compounds. The invention further relates to pharmaceutical compositions comprising such compounds optionally in combination with two or more different therapeutic agents and the use of such compounds in methods for treating diseases and conditions mediated and modulated by the GABA B receptor positive allosteric mechanism. The invention also provides a method for manufacture of medicaments useful in the treatment of such disorders.
• Discovery of 7-Oxopyrazolo[1,5-<i>a</i>]pyrimidine-6-carboxamides as Potent and Selective CB₂ Cannabinoid Receptor Inverse Agonists
  作者：Mojgan Aghazadeh Tabrizi、Pier Giovanni Baraldi、Giulia Saponaro、Allan R. Moorman、Romeo Romagnoli、Delia Preti、Stefania Baraldi、Emanuela Ruggiero、Cristina Tintori、Tiziano Tuccinardi、Fabrizio Vincenzi、Pier Andrea Borea、Katia Varani

  DOI：10.1021/jm400182t

  日期：2013.6.13

  We recently described the medicinal chemistry of a new series of heteroaryl-4-oxopyridine/7-oxopyrimidines as CB2 receptor partial agonists, showing that the functionality of these ligands is controlled by the nature of the heteroaryl function condensed with the pyridine ring. We describe herein the design and synthesis of the 7-oxopyrazolo[1,5-a]pyrimidine-6-carboxamides, structural isomers of our previously reported pyrazolo[3,4-Hpyridines. All of the new compounds showed high affinity and selectivity for the CB2 receptor in the nanomolar range. In 3,5-cyclic adenosine monophosphate (cAMP) assays, the novel series shows stimulatory effects on forskolin-induced cAMP production acting as inverse agonists.