6-(5-Methyl-2-Furyl)-5-Nitropyrimidine-2,4-Diamine | 442910-17-0

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 6-(5-Methyl-2-Furyl)-5-Nitropyrimidine-2,4-Diamine
• 英文别名: 6-(5-methylfuran-2-yl)-5-nitropyrimidine-2,4-diamine
• CAS: 442910-17-0
• 化学式: C₉H₉N₅O₃
• 分子量: 235.202
• InChiKey: VPUOJYLSZNTWOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  137
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-(5-Methyl-2-Furyl)-5-Nitropyrimidine-2,4-Diamine 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以99%的产率得到6-(5-methyl-2-furyl)pyrimidine-2,4,5-triamine
  参考文献：
  名称：

  人类A 2A腺苷受体的拮抗剂。4. 7-芳基三唑并[4,5- d ]嘧啶的设计，合成及临床前评价

  摘要：

  人类A 2A受体的拮抗作用被认为是减轻与帕金森氏病有关的症状的治疗干预点。认为这至少部分地通过增加多巴胺能神经元对残留的，耗尽的纹状体多巴胺水平的敏感性而发生。我们在此描述了一系列新颖的功能化的三唑并[4，5- d ]嘧啶衍生物，其显示出对A 2A受体的功能拮抗作用。这些化合物的优化已导致关键衍生物的效能，选择性和药代动力学特性得到改善。这些努力导致发现了60（V2006 / BIIB014），其在帕金森氏病的常用模型中证明了强烈的口服活性。此外，该衍生物已显示出优异的临床前药代动力学，并已成功完成I期临床研究。目前，该化合物正在与Biogen Idec合作进行进一步的临床评估。

  DOI：

  10.1021/jm800961g
• 作为产物：
  描述：

  5-甲基呋喃-2-硼酸 、 6-氯-5-硝基嘧啶-2,4-二胺 在 四(三苯基膦)钯 、 碳酸氢钠 作用下， 以 四氢呋喃 、 水 为溶剂， 以72%的产率得到6-(5-Methyl-2-Furyl)-5-Nitropyrimidine-2,4-Diamine
  参考文献：
  名称：

  人类A 2A腺苷受体的拮抗剂。4. 7-芳基三唑并[4,5- d ]嘧啶的设计，合成及临床前评价

  摘要：

  人类A 2A受体的拮抗作用被认为是减轻与帕金森氏病有关的症状的治疗干预点。认为这至少部分地通过增加多巴胺能神经元对残留的，耗尽的纹状体多巴胺水平的敏感性而发生。我们在此描述了一系列新颖的功能化的三唑并[4，5- d ]嘧啶衍生物，其显示出对A 2A受体的功能拮抗作用。这些化合物的优化已导致关键衍生物的效能，选择性和药代动力学特性得到改善。这些努力导致发现了60（V2006 / BIIB014），其在帕金森氏病的常用模型中证明了强烈的口服活性。此外，该衍生物已显示出优异的临床前药代动力学，并已成功完成I期临床研究。目前，该化合物正在与Biogen Idec合作进行进一步的临床评估。

  DOI：

  10.1021/jm800961g

文献信息

• [EN] TRIAZOLO[4,5-d] PYRIMIDINE DERIVATIVES AND THEIR USE AS PURINERGIC RECEPTOR ANTAGONISTS<br/>[FR] DERIVES DE TRIAZOLO[4,5-D] PYRIMIDINE ET LEUR UTILISATION EN TANT QU'AGONISTES DE RECEPTEUR PURINERGIQUE
  申请人：VERNALIS RES LTD

  公开号：WO2002055083A1

  公开（公告）日：2002-07-18

  The use of a compound of formula (I): wherein R1 is selected from H, alkyl, aryl, alkoxy, aryloxy, alkylthio, arylthio, halogen, CN, NR5R6, NR4COR5, NR4CONR5R6,NR4CO2R7 and NR4SO2R7; R2 is selected from aryl attached via an unsaturated carbon; R3 is selected from H, alkyl, COR5, CO2 R7, CONR5R6, CONR4NR5R6 and SO2R7; R4, R5 and R6 are independently selected from H, alkyl and aryl or where R5 and R6 are in an NR5R6 group, R5 and R6 may be linked to form a heterocyclic group, or where R4,R5 and R6 are in a (CONR4NR5R6) group, R4 and R5 may be linked to form a heterocyclic group; and R7 is selected from alkyl and aryl, or a pharmaceutically acceptable salt thereof or prodrug thereof, in the treatment or prevention of a disorder in which the blocking of purine receptors, particularly adenosine receptors and more particularly A2A receptors, may be beneficial, particularly wherein said disorder is a movement disorder such as Parkinson's disease or said disorder is depression, cognitive or memory impairment, acute or chronic pain, ADHD or narcolepsy, or for neuroprotection in a subject; compounds of formula (I) for use in therapy; and novel compounds of formula (I) per se.

  使用式(I)的化合物，其中R1从H，烷基，芳基，烷氧基，芳氧基，烷硫基，芳硫基，卤素，CN，NR5R6，NR4COR5，NR4CONR5R6，NR4CO2R7和NR4SO2R7中选择；R2从通过不饱和碳连接的芳基中选择；R3从H，烷基，COR5，CO2R7，CONR5R6，CONR4NR5R6和SO2R7中选择；R4，R5和R6独立地从H，烷基和芳基中选择，或者当R5和R6在NR5R6基团中时，R5和R6可以连接形成杂环基团，或者当R4，R5和R6在(CONR4NR5R6)基团中时，R4和R5可以连接形成杂环基团；R7从烷基和芳基中选择，或其药学上可接受的盐或前药，在治疗或预防阻断嘌呤受体，特别是腺苷受体，更具体地是A2A受体可能有益的疾病中使用，特别是其中所述疾病是运动障碍，如帕金森病，或所述疾病是抑郁症，认知或记忆障碍，急性或慢性疼痛，ADHD或嗜睡症，或用于保护神经系统。式(I)的化合物用于治疗；以及式(I)的新化合物本身。
• Triazolo[4,5-d]pyrimidine derivatives and their use as purinergic receptor antagonists
  申请人：——

  公开号：US20040097526A1

  公开（公告）日：2004-05-20

  The use of a compound of formula (1): wherein R 1 is selected from H, alkyl, aryl, alkoxy, aryloxy, alkylthio, arylthio, halogen, CN, NR 5 R 6 , NR 4 CONR 5 R 6 , NR 4 CONR 5 R 6 NR 4 CO 2 R 7 and NR 4 SO 2 R 7 ; R 2 is selected from aryl attached via an unsaturated carbon; R 3 is selected from H, alkyl, COR 5 , CO 2 R 7 , CONR 5 R 6 , CONR 4 NR 5 R 6 and SO 2 R 7 ; R 4 , R 5 and R 6 are independently selected from H, alkyl and aryl or where R 5 and R 6 are in an NR 5 R 6 group, R 5 and R 6 may be linked to form a heterocyclic group, or where R 4 ,R 5 and R 6 are in a (CONR 4 NR 5 R 6 ) group, R 4 and R 5 may be linked to form a heterocyclic group; and R 7 is selected from alkyl and aryl, or a pharmaceutically acceptable salt thereof or prodrug thereof, in the treatment or prevention of a disorder in which the blocking of purine receptors, particularly adenosine receptors and more particularly A 2A receptors, may be beneficial, particularly wherein said disorder is a movement disorder such as Parkinson's disease or said disorder is depression, cognitive or memory impairment, acute or chronic pain, ADHD or narcolepsy, or for neuroprotection in a subject; compounds of formula (I) for use in therapy; and novel compounds of formula (I) per se. 1

  使用式（1）的化合物：其中R1选自H，烷基，芳基，烷氧基，芳氧基，烷硫基，芳硫基，卤素，CN，NR5R6，NR4CONR5R6，NR4CONR5R6NR4CO2R7和NR4SO2R7；R2选自通过不饱和碳连接的芳基；R3选自H，烷基，COR5，CO2R7，CONR5R6，CONR4NR5R6和SO2R7；R4，R5和R6独立地选自H，烷基和芳基，或者当R5和R6在NR5R6组中时，R5和R6可以连接形成杂环基团，或者当R4，R5和R6在（CONR4NR5R6）组中时，R4和R5可以连接形成杂环基团；以及R7选自烷基和芳基，或其药学上可接受的盐或前药，用于治疗或预防阻断嘌呤受体，特别是腺苷受体，尤其是A2A受体，可能有益的疾病，特别是该疾病为运动障碍，如帕金森病，或该疾病为抑郁症，认知或记忆障碍，急性或慢性疼痛，ADHD或嗜睡症，或用于主体的神经保护；式（I）的化合物用于治疗；以及式（I）的新化合物本身。
• Triazolo[4,5-d] pyramidine derivatives and their use as purinergic receptor antagonists
  申请人：Gillespie Roger John

  公开号：US20080234296A1

  公开（公告）日：2008-09-25

  The use of a compound of formula (I): wherein R 1 is selected from H, alkyl, aryl, alkoxy, aryloxy, alkylthio, arylthio, halogen, CN, NR 5 R 6 , NR 4 COR 5 , NR 4 CONR 5 R 6 , NR 4 CO 2 R 7 and NR 4 SO 2 R 7 ; R 2 is selected from aryl attached via an unsaturated carbon; R 3 is selected from H, alkyl, COR 5 , CO 2 R 7 , CONR 5 R 6 , CONR 4 NR 5 R 6 and SO 2 R 7 ; R 4 , R 5 and R 6 are independently selected from H, alkyl and aryl or where R 5 and R 6 are in an NR 5 R 6 group, R 5 and R 6 may be linked to form a heterocyclic group, or where R 4 , R 5 and R 6 are in a (CONR 4 NR 5 R 6 ) group, R 4 and R 5 may be linked to form a heterocyclic group; and R 7 is selected from alkyl and aryl, or a pharmaceutically acceptable salt thereof or prodrug thereof, in the treatment or prevention of a disorder in which the blocking of purine receptors, particularly adenosine receptors and more particularly A 2A receptors, may be beneficial, particularly wherein said disorder is a movement disorder such as Parkinson's disease or said disorder is depression, cognitive or memory impairment, acute or chronic pain, ADHD or narcolepsy, or for neuroprotection in a subject; compounds of formula (I) for use in therapy; and novel compounds of formula (I) per se.

  使用公式（I）的化合物，其中R1从H，烷基，芳基，烷氧基，芳氧基，烷硫基，芳硫基，卤素，CN，NR5R6，NR4COR5，NR4CONR5R6，NR4CO2R7和NR4SO2R7中选择；R2从通过不饱和碳连接的芳基中选择；R3从H，烷基，COR5，CO2R7，CONR5R6，CONR4NR5R6和SO2R7中选择；R4，R5和R6分别从H，烷基和芳基中选择，或者当R5和R6在NR5R6中时，它们可以连接形成杂环基团，或者当R4，R5和R6在（CONR4NR5R6）基团中时，R4和R5可以连接形成杂环基团；并且R7从烷基和芳基中选择，或其药学上可接受的盐或前药，在治疗或预防阻断嘌呤受体，特别是腺苷受体，尤其是A2A受体可能有益的疾病中使用，特别是其中所述的疾病是运动障碍，如帕金森病，或所述的疾病是抑郁症，认知或记忆障碍，急性或慢性疼痛，注意力缺陷多动障碍或嗜睡症，或用于保护神经系统。公式（I）的化合物用于治疗；以及公式（I）的新型化合物本身。
• Triazolo [4,5-d] pyrimidine derivatives and their use as purinergic receptor antagonists
  申请人：Gillespie John Roger

  公开号：US20070049607A1

  公开（公告）日：2007-03-01

  The use of a compound of formula (I): wherein R 1 is selected from H, alkyl, aryl, alkoxy, aryloxy, alkylthio, arylthio, halogen, CN, NR 5 R 6 , NR 4 COR 5 , NR 4 CONR 5 R 6 , NR 4 CO 2 R 7 and NR 4 SO 2 R 7 ; R 2 is selected from aryl attached via an unsaturated carbon; R 3 is selected from H, alkyl, COR 5 , CO 2 R 7 , CONR 5 R 6 , CONR 4 NR 5 R 6 and SO 2 R 7 ; R 4 , R 5 and R 6 are independently selected from H, alkyl and aryl or where R 5 and R 6 are in an NR 5 R 6 group, R 5 and R 6 may be linked to form a heterocyclic group, or where R 4 , R 5 and R 6 are in a (CONR 4 NR 5 R 6 ) group, R 4 and R 5 may be linked to form a heterocyclic group; and R 7 is selected from alkyl and aryl, or a pharmaceutically acceptable salt thereof or prodrug thereof, in the treatment or prevention of a disorder in which the blocking of purine receptors, particularly adenosine receptors and more particularly A 2A receptors, may be beneficial, particularly wherein said disorder is a movement disorder such as Parkinson's disease or said disorder is depression, cognitive or memory impairment, acute or chronic pain, ADHD or narcolepsy, or for neuroprotection in a subject; compounds of formula (I) for use in therapy; and novel compounds of formula (I) per se.

  使用化合物式(I)的化合物：其中R1从H、烷基、芳基、烷氧基、芳氧基、烷硫基、芳硫基、卤素、CN、NR5R6、NR4COR5、NR4CONR5R6、NR4CO2R7和NR4SO2R7中选择；R2从通过不饱和碳连接的芳基中选择；R3从H、烷基、COR5、CO2R7、CONR5R6、CONR4NR5R6和SO2R7中选择；R4、R5和R6分别从H、烷基和芳基中选择，或者当R5和R6在NR5R6组中时，R5和R6可以连接形成杂环基团，或者当R4、R5和R6在(CONR4NR5R6)组中时，R4和R5可以连接形成杂环基团；以及R7从烷基和芳基中选择，或其药学上可接受的盐或前药，在治疗或预防阻断嘌呤受体特别是腺苷受体，尤其是A2A受体可能有益的疾病中使用，特别是其中所述疾病是运动障碍如帕金森病或所述疾病是抑郁症、认知或记忆障碍、急性或慢性疼痛、ADHD或嗜睡症，或用于对受试者进行神经保护；化合物式(I)的化合物用于治疗；以及化合物式(I)的新化合物本身。
• Triazol[4,5-d] pyramidine derivatives and their use as purinergic receptor antagonists
  申请人：Vernalis Research Limited

  公开号：US07589097B2

  公开（公告）日：2009-09-15

  The use of a compound of formula (I): wherein R1 is selected from H, alkyl, aryl, alkoxy, aryloxy, alkylthio, arylthio, halogen, CN, NR5R6, NR4COR5, NR4CONR5R6, NR4CO2R7 and NR4SO2R7; R2 is selected from aryl attached via an unsaturated carbon; R3 is selected from H, alkyl, COR5, CO2R7, CONR5R6, CONR4NR5R6 and SO2R7; R4, R5 and R6 are independently selected from H, alkyl and aryl or where R5 and R6 are in an NR5R6 group, R5 and R6 may be linked to form a heterocyclic group, or where R4, R5 and R6 are in a (CONR4NR5R6) group, R4 and R5 may be linked to form a heterocyclic group; and R7 is selected from alkyl and aryl, or a pharmaceutically acceptable salt thereof or prodrug thereof, in the treatment or prevention of a disorder in which the blocking of purine receptors, particularly adenosine receptors and more particularly A2A receptors, may be beneficial, particularly wherein said disorder is a movement disorder such as Parkinson's disease or said disorder is depression, cognitive or memory impairment, acute or chronic pain, ADHD or narcolepsy, or for neuroprotection in a subject; compounds of formula (I) for use in therapy; and novel compounds of formula (I) per se.

  使用公式（I）的化合物，其中R1从H，烷基，芳基，烷氧基，芳氧基，烷硫基，芳硫基，卤素，CN，NR5R6，NR4COR5，NR4CONR5R6，NR4CO2R7和NR4SO2R7中选择；R2从通过不饱和碳连接的芳基中选择；R3从H，烷基，COR5，CO2R7，CONR5R6，CONR4NR5R6和SO2R7中选择；R4，R5和R6独立地从H，烷基和芳基中选择，或者当R5和R6在NR5R6组中时，R5和R6可以连接形成杂环基团，或者当R4，R5和R6在（CONR4NR5R6）组中时，R4和R5可以连接形成杂环基团；以及R7从烷基和芳基中选择，或其药学上可接受的盐或前药，用于治疗或预防阻断嘌呤受体，特别是腺苷受体，更特别是A2A受体可能有益的疾病，特别是其中所述疾病是运动障碍，例如帕金森病，或所述疾病是抑郁症，认知或记忆障碍，急性或慢性疼痛，ADHD或嗜睡症，或用于对受试者进行神经保护；化合物（I）用于治疗的用途；以及公式（I）的新化合物本身。