5,6-bis(4-methoxyphenyl)-pyrazine-2-carboxylic acid | 122956-28-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5,6-bis(4-methoxyphenyl)-pyrazine-2-carboxylic acid
• 英文别名: 2,3-bis(p-methoxyphenyl)-5-pyrazinecarboxylic acid；5,6-bis-(4-methoxy-phenyl)-pyrazine-2-carboxylic acid；5,6-Bis-(4-methoxy-phenyl)-pyrazin-2-carbonsaeure；5,6-Bis(4-methoxyphenyl)pyrazine-2-carboxylic acid
• CAS: 122956-28-9
• 化学式: C₁₉H₁₆N₂O₄
• 分子量: 336.347
• InChiKey: GWGILOWBUBUWOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  81.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5,6-bis(4-methoxyphenyl)-pyrazine-2-carboxylic acid 、 1-氨基哌啶 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以19%的产率得到5,6-bis(4-methoxyphenyl)-N-(piperidin-1-yl)pyrazine-2-carboxamide
  参考文献：
  名称：

  5,6-二芳基-吡嗪-2-酰胺衍生物的支架跳跃，合成和构效关系：一种新型的CB1受体拮抗剂。

  摘要：

  已经开发出一种支架跳跃方法来设计用于治疗肥胖症的新型大麻素（CB1）受体拮抗剂。基于形状互补性和合成可行性，利莫那班的中心片段甲基吡唑被吡嗪取代。描述了一系列新的5,6-二芳基-吡嗪-2-酰胺衍生物的合成和CB1拮抗活性。几种化合物对CB1受体的拮抗药效力低于10nM。

  DOI：

  10.1016/j.bmc.2007.03.075
• 作为产物：
  描述：

  2,3-双(对甲氧基苯基)-5-氰基吡嗪 在 氢氧化钾 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 4.0h， 以95%的产率得到5,6-bis(4-methoxyphenyl)-pyrazine-2-carboxylic acid
  参考文献：
  名称：

  Anti-Platelet Aggregation Activity of Some Pyrazines.

  摘要：

  本报告介绍了 48 种吡嗪类化合物的抗血小板聚集活性。在测试的烷基和芳基吡嗪中，2, 3-二苯基吡嗪的抗血小板聚集活性最强。然后，在苯基上引入了各种取代基，结果发现 2，3-双（对甲氧基苯基）吡嗪衍生物具有相当强的抑制活性。

  DOI：

  10.1248/bpb.20.1076

文献信息

• Stable dispersion of solid particles comprising a water-insoluble pyrazine compound
  申请人：Lindfors Lennart

  公开号：US20060134146A1

  公开（公告）日：2006-06-22

  A process for the preparation of a stable dispersion of solid particles, in an aqueous medium comprising combining (a) a first solution comprising a substantially water-insoluble substance which is a pyrazine compound of Formula I, a water-miscible organic solvent and an inhibitor with (b) an aqueous phase comprising water and optionally a stabiliser, thereby precipitating solid particles comprising the inhibitor and the substantially water-insoluble substance; and optionally removing the water-miscible organic solvent; wherein the inhibitor is a non-polymeric hydrophobic organic compound as defined in the description. Also claimed are stable dispersions prepared by the process, solid particles prepared by the process and use of such particles.

  一种制备稳定固体颗粒分散液的方法，其中包括将（a）第一溶液与（b）水相结合，从而沉淀出包含抑制剂和基本上不溶于水的Formula I吡嗪化合物的固体颗粒，所述第一溶液包括基本上不溶于水的物质、水相溶的有机溶剂和抑制剂，可选地还包括稳定剂；并可选地去除水相溶的有机溶剂；其中所述抑制剂是描述中定义的非聚合疏水有机化合物。此外，还声明了通过该方法制备的稳定分散液、通过该方法制备的固体颗粒以及使用这些颗粒的用途。
• 5 6-diaryl-pyrazine-2-amide derivatives as cb1 antagonists
  申请人：Berggren Ingrid Kristina Anna

  公开号：US20050032808A1

  公开（公告）日：2005-02-10

  The present invention relates to compounds of formula (I), and pharmaceutically acceptable salts, prodrugs, solvates and crystalline forms thereof, in which R 1 and R 2 independently represent: a C 1-6 alkyl group; an optionally substituted (amino)C 1-4 alkyl-group; an optionally substituted non-aromatic C 3-15 carbocyclic group; a (C 3-12 cycloalkyl)C 1-3 alkyl-group; a group —(CH 2 ) r (phenyl) s in which r is 0, 1, 2, 3 or 4, s is 1 when r is 0 otherwise s is 1 or 2 and the phenyl groups are optionally independently substituted by Z; naphthyl; anthracenyl; an optionally substituted saturated 5 to 8 membered heterocyclic group containing one nitrogen and optionally one of the following: oxygen, sulphur or an additional nitrogen; 1-adamantylmethyl; a group —(CH 2 ) t Het in which t is 0, 1, 2, 3 or 4, and the alkylene chain is optionally substituted and Het represents an optionally substituted aromatic heterocycle; or R 1 represents H and R 2 is as defined above; or R 1 and R 2 together with the nitrogen atom to which they are attached represent a saturated optionally substituted 5 to 8 membered heterocyclic group as defined above; X is CO or SO 2 ; Y is absent or represents NH optionally substitututed by a C 1-3 alkyl group; R 3 and R 4 independently represent phenyl, thienyl or pyridyl substituted by Z; Z represents a C 1-3 alkyl group, a C 1-3 alkoxy group, hydroxy, halo, trifluoromethyl, trifluoromethylthio, trifluoromethoxy, trifluoromethylsulphonyl, nitro, amino, mono or di C 1-3 alkylamino, mono or di C 1-3 alkylamido, C 1-3 alkylsulphonyl, C 1-3 alkoxycarbonyl, carboxy, cyano, carbamoyl, mono or di C 1-3 alkyl carbamoyl, sulphamoyl and acetyl; and R 5 is H, a C 1-3 alkyl group, a C 1-3 alkoxymethyl group, trifluoromethyl, a hydroxyC 1-3 alkyl group, C 1-3 alkoxycarbonyl, carboxy, cyano, carbamoyl, mono or di C 1-3 alkylcarbamoyl, acetyl, or hydrazinocarbonyl of formula —CONHNR a R b ; with the provisos; and processes for preparing such compounds, their use in the treatment of obesity, psychiatric and neurological disorders, to methods for their therapeutic use and to pharmaceutical compositions containing them.

  本发明涉及化合物(I)及其药学上可接受的盐、前药、溶剂和晶体形式，其中R1和R2分别代表：C1-6烷基；可选地取代的（氨基）C1-4烷基基团；可选地取代的非芳香性C3-15环烷基团；（C3-12环烷基）C1-3烷基基团；—（CH2）r（苯基）s，其中r为0、1、2、3或4，s为1时r为0，否则s为1或2，苯基可以独立地被Z取代；萘基；蒽基；可选地取代的饱和的5至8元杂环基团，其中包含一个氮和可选的以下之一：氧、硫或另一个氮；1-金刚烷基甲基；—（CH2）tHet，其中t为0、1、2、3或4，烷基链可选地被取代，Het代表可选地取代的芳香杂环；或R1代表H，R2如上所定义；或R1和R2与它们连接的氮原子一起表示如上所定义的饱和可选地取代的5至8元杂环基团；X为CO或SO2；Y不存在或代表可选地取代的C1-3烷基基团的NH；R3和R4分别表示被Z取代的苯基、噻吩基或吡啶基；Z代表C1-3烷基基团、C1-3烷氧基基团、羟基、卤、三氟甲基、三氟甲硫基、三氟甲氧基、三氟甲基磺酰基、硝基、氨基、单或双C1-3烷基氨基、单或双C1-3烷基酰胺基、C1-3烷基磺酰基、C1-3烷氧基羰基、羧基、氰基、氨基甲酰基、单或双C1-3烷基氨基甲酰基、磺酰胺基和乙酰基；R5为H、C1-3烷基基团、C1-3烷氧甲基基团、三氟甲基、羟基C1-3烷基基团、C1-3烷氧羰基、羧基、氰基、氨基甲酰基、单或双C1-3烷基氨基甲酰基、乙酰基或公式—CONHNRaRb的肼基，其中Ra和Rb分别为H或C1-3烷基；但需要注意的是，本发明还涉及制备这些化合物的方法、它们在肥胖症、精神和神经疾病治疗中的用途以及含有它们的制药组合物。
• PYRAZINE DERIVATIVES AND MEDICINAL PREPARATION CONTAINING SAME
  申请人：TERUMO KABUSHIKI KAISHA

  公开号：EP0397859A1

  公开（公告）日：1990-11-22

  Pyrazine derivatives represented by general formula (I), wherein X represents a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group or a cyano group, R1 represents a hydrogen atom, a lower alkyl group or a group of (a) (wherein X is as defined above), R2 represents a hydrogen atom, a halogen atom or (a) (wherein X is as defined above), R3 represents a hydrogen atom, a halogen atom, a lower alkyl group, a cyano group, a naphthylmethyl group, a benzyl group or (b) (wherein R4represents a hydrogen atom, a halogen atom or a lower alkylamino group), a carboxyl group or a lower alkoxycarbonyl group or, when taken together, R2 and R3 represent a cyclohexane ring or a benzene ring together with the carbon atoms to which they are bound, provided that the case where X represents a hydrogen atom, R, represents (a) (wherein X represents a hydrogen atom), and R2 and R3 represent hydrogen atoms and the case where X represents a hydrogen atom, R1 represents a hydrogen atom, R2 represents (a) (wherein X represents a hydrogen atom), and R3 represents a methyl group are excluded. The pyrazine derivatives have a strong blood platelet agglutination depressing effect and a cyclooxygenase inhibiting effect. The above-described compounds are used as blood platelet agglutination inhibitor or anti-inflammatory agents.

  通式(I)代表的吡嗪衍生物，其中X代表氢原子、卤素原子、低级烷基、低级烷氧基或氰基，R1代表氢原子、低级烷基或(a)基团(其中X如上定义)，R2代表氢原子、卤素原子或(a)基团(其中X如上定义)，R3代表氢原子、卤素原子、低级烷基、氰基、腈基、R3 代表氢原子、卤素原子、低级烷基、氰基、萘甲基、苄基或 (b) 基团（其中 R4 代表氢原子、卤素原子或低级烷基氨基）、羧基或低级烷氧羰基，或者当 R2 和 R3 结合在一起时，R2 和 R3 与它们所结合的碳原子一起代表环己烷环或苯环，但不包括 X 代表氢原子、R 代表(a)（其中 X 代表氢原子）、R2 和 R3 代表氢原子的情况，以及 X 代表氢原子、R1 代表氢原子、R2 代表(a)（其中 X 代表氢原子）、R3 代表甲基的情况。吡嗪衍生物具有很强的血小板凝集抑制作用和环氧化酶抑制作用。上述化合物可用作血小板凝集抑制剂或抗炎剂。
• Mason; Dryfoos, Journal of the Chemical Society, 1893, vol. 63, p. 1296
  作者：Mason、Dryfoos

  DOI：——

  日期：——
• 5,6-DIARYL-PYRAZINE-2-AMIDE DERIVATIVES AS CB1 ANTAGONISTS
  申请人：AstraZeneca AB

  公开号：EP1458690B1

  公开（公告）日：2007-02-21