2-(piperazin-1-yl)oxazolo[4,5-b]pyridine | 113520-22-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 2-(piperazin-1-yl)oxazolo[4,5-b]pyridine
• 英文别名: 2-Piperazin-1-yl[1,3]oxazolo[4,5-b]pyridine；2-piperazin-1-yl-[1,3]oxazolo[4,5-b]pyridine
• CAS: 113520-22-2
• 化学式: C₁₀H₁₂N₄O
• mdl: MFCD09743365
• 分子量: 204.231
• InChiKey: GSHPHBYVQTWDMY-UHFFFAOYSA-N

物化性质

• 熔点：
  80-81 °C
• 沸点：
  358.3±52.0 °C(Predicted)
• 密度：
  1.267±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  54.2
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  2-(piperazin-1-yl)oxazolo[4,5-b]pyridine 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 异丙醇 为溶剂， 反应 17.0h， 生成 (R)-1-[4-(4-Oxazolo[4,5-b]pyridin-2-yl-piperazin-1-yl)-pyrimidin-2-yl]-ethanol
  参考文献：
  名称：

  Orally-Effective, Long-Acting Sorbitol Dehydrogenase Inhibitors:  Synthesis, Structure−Activity Relationships, and in Vivo Evaluations of Novel Heterocycle-Substituted Piperazino-Pyrimidines

  摘要：

  Optimization of a previously disclosed sorbitol dehydrogenase inhibitor (SDI, II) for potency and duration of action was achieved by replacing the metabolically labile N,N-dimethylsulfamoyl group with a variety of heterocycles. Specifically, this effort led to a series of novel, in vitro potent SDIs with longer serum half-lives and acceptable in vivo activity in acutely diabetic rats (e.g., 62, 67, and 69). However, the desired in vivo potency in chronically diabetic rats, ED90 less than or equal to 5 mg/kg/day, was achieved only through further modification of the piperazine linker. Several members of this family, including 86, showed better than the targeted potency with ED90 values of 1-2 mg/kg/day. Compound 86 was further profiled and found to be a selective inhibitor of sorbitol dehydrogenase, with excellent pharmacodynamic/pharmacokinetic properties, demonstrating normalization of sciatic nerve fructose in a chronically diabetic rat model for similar to17 h, when administered orally at a single dose of 2 mg/kg/day.

  DOI：

  10.1021/jm010440g
• 作为产物：
  描述：

  2-氨基-3-羟基吡啶 在 potassium hydroxide 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 26.0h， 生成 2-(piperazin-1-yl)oxazolo[4,5-b]pyridine
  参考文献：
  名称：

  Venkatachalam; Pierens; Reutens, Letters in Organic Chemistry, 2010, vol. 7, # 7, p. 519 - 527

  摘要：

  DOI：

文献信息

• [EN] HETEROCYCLIC COMPOUNDS AS INHIBITORS OF MONOACYLGLYCEROL LIPASE (MAGL)<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES EN TANT QU'INHIBITEURS DE LA MONOACYLGLYCÉROL LIPASE (MAGL)
  申请人：HOFFMANN LA ROCHE

  公开号：WO2020207941A1

  公开（公告）日：2020-10-15

  The application relates to heterocyclic compounds of the general formula (I), compositions comprising such compounds, a process for preparing these compounds and their medical use. The compounds act as monoacylglycerol lipase (MAGL) inhibitors and are useful in the treatment of neuroinflammation, neurodegenerative diseases, pain, cancer or mental disorders.

  该申请涉及一类通式为(I)的杂环化合物，包含这些化合物的组合物，这些化合物的制备方法以及它们的医疗用途。这些化合物作为单酰基甘油脂肪酶（MAGL）抑制剂，可用于治疗神经炎症、神经退行性疾病、疼痛、癌症或精神障碍。
• Proline derivatives and use thereof as drugs
  申请人：Kitajima Hiroshi

  公开号：US20050245538A1

  公开（公告）日：2005-11-03

  The present invention aims at providing compounds having therapeutic effects due to a DPP-IV inhibitory action, and satisfactory as pharmaceutical products. The present inventors have found that derivatives having a substituent introduced into the γ-position of proline represented by the formula (I) wherein each symbol is as defined in the specification, have a potent DPP-IV inhibitory activity, and completed the present invention by increasing the stability.

  本发明旨在提供具有治疗效果的化合物，其作用是通过DPP-IV的抑制作用，并且作为药物产品具有令人满意的效果。本发明人发现，在丙氨酸的γ位上引入取代基的衍生物具有强效的DPP-IV抑制活性，并通过增加稳定性完成了本发明。
• Proline derivatives and the use thereof as drugs
  申请人：——

  公开号：US20040106655A1

  公开（公告）日：2004-06-03

  The present invention aims at providing compounds having therapeutic effects due to a DPP-IV inhibitory action, and satisfactory as pharmaceutical products. The present inventors have found that derivatives having a substituent introduced into the &ggr;-position of proline represented by the formula (I) 1 wherein each symbol is as defined in the specification, have a potent DPP-IV inhibitory activity, and completed the present invention by increasing the stability.

  本发明旨在提供具有治疗作用的化合物，由于DPP-IV抑制作用而具有满意的药物产品。本发明人发现，具有引入取代基的脯氨酸γ-位置的衍生物，其化学式为(I)1，其中每个符号如规范中所定义，具有强效的DPP-IV抑制活性，并通过增加稳定性完成了本发明。
• PROLINE DERIVATIVES AND USE THEREOF AS DRUGS
  申请人：Mitsubishi Tanabe Pharma Corporation

  公开号：EP1308439B1

  公开（公告）日：2008-10-15
• Reaction of 3H-oxazolo[4,5-b]pyridine-2-thione with amines
  作者：K. Davidkov、D. Simov、V. Kalcheva

  DOI：10.1007/bf00473472

  日期：1987.8