1H-吡唑并[3,4-c]吡嗪-3(2H)-酮 | 2125-85-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并吡啶类
• 中文名称: 1H-吡唑并[3,4-c]吡嗪-3(2H)-酮
• 中文别名: 1H-吡唑并[3,4-C]哒嗪-3(2H)-酮
• 英文名称: 3-hydroxypyrazolo<3,4-c>pyridazine
• 英文别名: 1H-pyrazolo[3,4-c]pyridazin-3-ol；3-Hydroxy-1H-pyrazolo<3,4-c>pyridazin；1,2-dihydro-pyrazolo[3,4-c]pyridazin-3-one；1H-Pyrazolo[3,4-c]pyridazin-3(2H)-one；1,2-dihydropyrazolo[3,4-c]pyridazin-3-one
• CAS: 2125-85-1
• 化学式: C₅H₄N₄O
• 分子量: 136.113
• InChiKey: DWNDGHRTRSFQFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.9
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  1H-吡唑并[3,4-c]吡嗪-3(2H)-酮 在 sodium methylate 、 caesium carbonate 、 三乙胺 、 三溴氧磷 作用下， 以 环丁砜 、 甲醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-c]pyridazin-3-yl]-5-[(E)-phenyldiazenyl]pyrimidine-4,6-diamine
  参考文献：
  名称：

  Discovery of the Soluble Guanylate Cyclase Stimulator Vericiguat (BAY 1021189) for the Treatment of Chronic Heart Failure

  摘要：

  The first-in-class soluble guanylate cyclase (sGC) stimulator riociguat was recently introduced as a novel treatment option for pulmonary hypertension. Despite its outstanding pharmacological profile, application of riociguat in other cardiovascular indications is limited by its short half-life, necessitating a three times daily dosing regimen. In our efforts to further optimize the compound class, we have uncovered interesting structure activity relationships and were able to decrease oxidative metabolism significantly. These studies resulting in the discovery of once daily sGC stimulator vericiguat (compound 24, BAY 1021189), currently in phase 3 trials for chronic heart failure, are now reported.

  DOI：

  10.1021/acs.jmedchem.7b00449
• 作为产物：
  描述：

  2-氨基噻吩-3-羧酸甲酯 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 37.0h， 以64%的产率得到1H-吡唑并[3,4-c]吡嗪-3(2H)-酮
  参考文献：
  名称：

  Pyrazolo[3,4-c]pyridazines from hydrazine and aminothiophenecarboxylates

  摘要：

  DOI：

  10.1021/jo00029a046

文献信息

• Pyrazolo[3,4-c]pyridazines from hydrazine and aminothiophenecarboxylates
  作者：Manfred G. Reinecke、Thomas A. Woodrow、E. Sherwood Brown

  DOI：10.1021/jo00029a046

  日期：1992.1
• Discovery of the Soluble Guanylate Cyclase Stimulator Vericiguat (BAY 1021189) for the Treatment of Chronic Heart Failure
  作者：Markus Follmann、Jens Ackerstaff、Gorden Redlich、Frank Wunder、Dieter Lang、Armin Kern、Peter Fey、Nils Griebenow、Walter Kroh、Eva-Maria Becker-Pelster、Axel Kretschmer、Volker Geiss、Volkhart Li、Alexander Straub、Joachim Mittendorf、Rolf Jautelat、Hartmut Schirok、Karl-Heinz Schlemmer、Klemens Lustig、Michael Gerisch、Andreas Knorr、Hanna Tinel、Thomas Mondritzki、Hubert Trübel、Peter Sandner、Johannes-Peter Stasch

  DOI：10.1021/acs.jmedchem.7b00449

  日期：2017.6.22

  The first-in-class soluble guanylate cyclase (sGC) stimulator riociguat was recently introduced as a novel treatment option for pulmonary hypertension. Despite its outstanding pharmacological profile, application of riociguat in other cardiovascular indications is limited by its short half-life, necessitating a three times daily dosing regimen. In our efforts to further optimize the compound class, we have uncovered interesting structure activity relationships and were able to decrease oxidative metabolism significantly. These studies resulting in the discovery of once daily sGC stimulator vericiguat (compound 24, BAY 1021189), currently in phase 3 trials for chronic heart failure, are now reported.

表征谱图