5-甲基-N-(4-甲基嘧啶-2-基)-4-(1H-吡唑-4-基)噻唑-2-胺 | 1235318-89-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-甲基-N-(4-甲基嘧啶-2-基)-4-(1H-吡唑-4-基)噻唑-2-胺
• 中文别名: 4-甲基-n-[5-甲基-4-(1H-吡唑-4-基)-2-噻唑]-2-嘧啶胺；4-甲基-N-[5-甲基-4-(1H-吡唑-4-基)-2-噻唑基]-2-嘧啶胺
• 英文名称: ADX88178
• 英文别名: 5-methyl-N-(4-methylpyrimidin-2-yl)-4-(1H-pyrazol-4-yl)thiazol-2-amine；5-methyl-N-(4-methylpyrimidin-2-yl)-4-(1H-pyrazol-4-yl)-1,3-thiazol-2-amine
• CAS: 1235318-89-4
• 化学式: C₁₂H₁₂N₆S
• 分子量: 272.333
• InChiKey: MIQNXKWDQRNHAU-UHFFFAOYSA-N

物化性质

• 溶解度：
  DMSO：16.67（最大浓度 mg/mL）；61.21（最大浓度 mM）

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 危险性防范说明：
  P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313
• 危险性描述：
  H315,H319

反应信息

• 作为产物：
  描述：

  在 三氟乙酸 作用下， 反应 3.0h， 以38%的产率得到5-甲基-N-(4-甲基嘧啶-2-基)-4-(1H-吡唑-4-基)噻唑-2-胺
  参考文献：
  名称：

  Radiosynthesis and evaluation of 5-methyl- N -(4-[ 11 C]methylpyrimidin-2-yl)-4-(1 H -pyrazol-4-yl)thiazol-2-amine ([ 11 C]ADX88178) as a novel radioligand for imaging of metabotropic glutamate receptor subtype 4 (mGluR4)

  摘要：

  ADX88178 (1) has been recently developed as a potent positive allosteric modulator for metabotropic glutamate receptor 4 (mGluR4). The aim of this study was to develop [C-11]1 as a novel positron emission tomography ligand and to evaluate its binding ability for mGluR4. Using stannyl precursor 3, [C-11]1 was efficiently synthesized by introducing an [C-11]methyl group into a pyrimidine ring via C-C-11 coupling and deprotection reactions, in 16 +/- 6% radiochemical yield (n = 10). At the end of synthesis, 0.54-1.10 GBq of [C-11]1 was acquired with > 98% radiochemical purity and 90-120 GBq/mu mol of specific activity. In vitro autoradiography and ex vivo biodistribution study in rat brains showed specific binding of [C-11]1 in the cerebellum, striatum, thalamus, cerebral cortex, and medulla oblongata, which showed dose-dependent decreases by administration with multi-dose of unlabeled 1. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.12.008

文献信息

• NOVEL THIAZOLES DERIVATIVES AND THEIR USE AS POSITIVE ALLOSTERIC MODULATORS OF METABOTROPIC GLUTAMATE RECEPTORS
  申请人：Bolea Christelle

  公开号：US20110257179A1

  公开（公告）日：2011-10-20

  The present invention relates to novel compounds of Formula (I), wherein M, P, A and (B) n are defined as in Formula (I); invention compounds are modulators of metabotropic glutamate receptors—subtype 4 (“mGluR4”) which are useful for the treatment or prevention of central nervous system disorders as well as other disorders modulated by mGluR4 receptors. The invention is also directed to pharmaceutical compositions and the use of such compounds in the manufacture of medicaments, as well as to the use of such compounds for the prevention and treatment of such diseases in which mGluR4 is involved.

  本发明涉及公式（I）的新化合物，其中M，P，A和（B）n如公式（I）中所定义；发明化合物是代谢型谷氨酸受体-亚型4（“mGluR4”）的调节剂，对于治疗或预防中枢神经系统疾病以及其他由mGluR4受体调节的疾病有用。本发明还涉及制药组合物以及使用这种化合物制造药物的用途，以及使用这种化合物预防和治疗涉及mGluR4的疾病的用途。
• NOVEL 2-AMINO-4-PYRAZOLYL-THIAZOLE DERIVATIVES AND THEIR USE AS ALLOSTERIC MODULATORS OF METABOTROPIC GLUTAMATE RECEPTORS
  申请人：Boléa Christelle

  公开号：US20130210809A1

  公开（公告）日：2013-08-15

  The present invention relates to novel compounds of Formula (1), wherein M, A and B are defined as in Formula (I); invention compounds are modulators of metabotropic glutamate receptors-subtype 4 (“mGluR4”) which are useful for the treatment or prevention of central nervous system disorders as well other disorders modulated by mGluR4 receptors. The invention is also directed to pharmaceutical compositions and the use of such compounds in the manufacture of medicaments, as well as to the use of such compounds for the prevention and treatment of such diseases in which mGluR4 is involved.

  本发明涉及式（1）的新化合物，其中M，A和B如式（I）中所定义; 发明化合物是代谢型谷氨酸受体亚型4（“mGluR4”）的调节剂，可用于治疗或预防中枢神经系统疾病以及其他受mGluR4受体调节的疾病。本发明还涉及制药组合物和使用这些化合物制造药物的用途，以及使用这些化合物预防和治疗mGluR4参与的疾病的用途。
• MODULATORS OF METABOTROPIC GLUTAMATE RECEPTOR 4
  申请人：The General Hospital Corporation

  公开号：US20220118117A1

  公开（公告）日：2022-04-21

  The present application provides picolinamide compounds that can be used as allosteric positron emission tomography (“PET”) imaging probes. Methods of using these compounds for treating a neurodegenerative disease are also provided.
• US9073907B2
  申请人：——

  公开号：US9073907B2

  公开（公告）日：2015-07-07
• [EN] NOVEL 2-AMINO-4-PYRAZOLYL-THIAZOLE DERIVATIVES AND THEIR USE AS ALLOSTERIC MODULATORS OF METABOTROPIC GLUTAMATE RECEPTORS<br/>[FR] NOUVEAUX DÉRIVÉS DE 2-AMINO-4-PYRAZOLYL-THIAZOLE ET LEUR UTILISATION EN TANT QUE MODULATEURS ALLOSTÉRIQUES DES RÉCEPTEURS MÉTABOTROPIQUES DU GLUTAMATE
  申请人：ADDEX PHARMACEUTICALS SA

  公开号：WO2012009009A2

  公开（公告）日：2012-01-19

  The present invention relates to novel compounds of Formula (1), wherein M, A and B are defined as in Formula (I); invention compounds are modulators of metabotropic glutamate receptors - subtype 4 ("mGluR4") which are useful for the treatment or prevention of central nervous system disorders as well as other disorders modulated by mGluR4 receptors. The invention is also directed to pharmaceutical compositions and the use of such compounds in the manufacture of medicaments, as well as to the use of such compounds for the prevention and treatment of such diseases in which mGluR4 is involved.