1-(tetrahydropyran-4-yl)-5-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1H-indole | 1255145-20-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-(tetrahydropyran-4-yl)-5-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1H-indole
• 英文别名: 1-(tetrahydro-pyran-4-yl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole；1-(oxan-4-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indole
• CAS: 1255145-20-0
• 化学式: C₁₉H₂₆BNO₃
• 分子量: 327.231
• InChiKey: RAVMQJCZAGDXFE-UHFFFAOYSA-N

物化性质

• 沸点：
  485.4±35.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.29
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  32.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-氯-3-(环丙基甲基)-7-碘-[1,2,4]三唑并[4,3-A]吡啶 、 1-(tetrahydropyran-4-yl)-5-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1H-indole 在 四(三苯基膦)钯 碳酸氢钠 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.17h， 以45%的产率得到8-chloro-3-(cyclopropylmethyl)-7,8-dihydro-7-[1-(tetrahydro-2H-pyran-4-yl)-1H-indol-5-yl]-1,2,4-triazolo[4,3-a]pyridine
  参考文献：
  名称：

  [EN] 1,2,4-TRIAZOLO[4,3-A]PYRIDINE DERIVATIVES AND THEIR USE AS POSITIVE ALLOSTERIC MODULATORS OF MGLUR2 RECEPTORS
  [FR] DÉRIVÉS DE LA 1,2,4-TRIAZOLO [4,3-A] PYRIDINE ET LEUR UTILISATION EN TANT QUE MODULATEURS ALLOSTÉRIQUES POSITIFS DES RÉCEPTEURS MGLUR2

  摘要：

  本发明涉及新型三唑并[4,3-a]吡啶衍生物的公式(I)，其中所有基团如权利要求中所定义。根据本发明的化合物是代谢型谷氨酸受体亚型2（"mGluR2"）的阳性变构调节剂，对于治疗或预防与谷氨酸功能障碍相关的神经和精神疾病以及代谢型受体的mGluR2亚型参与的疾病具有用处。本发明还涉及包括这种化合物的药物组合物，用于制备这种化合物和组合物的方法，以及利用这种化合物预防或治疗与mGluR2有关的神经和精神疾病和疾病。

  公开号：

  WO2010130422A1
• 作为产物：
  描述：

  5-Bromo-1-(tetrahydro-2H-pyran-4-yl)-1H-indole 、 联硼酸频那醇酯 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 potassium acetate 作用下， 以 1,4-二氧六环 为溶剂， 以74.6%的产率得到1-(tetrahydropyran-4-yl)-5-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1H-indole
  参考文献：
  名称：

  [EN] 1,2,4-TRIAZOLO[4,3-A]PYRIDINE DERIVATIVES AND THEIR USE AS POSITIVE ALLOSTERIC MODULATORS OF MGLUR2 RECEPTORS
  [FR] DÉRIVÉS DE LA 1,2,4-TRIAZOLO [4,3-A] PYRIDINE ET LEUR UTILISATION EN TANT QUE MODULATEURS ALLOSTÉRIQUES POSITIFS DES RÉCEPTEURS MGLUR2

  摘要：

  本发明涉及新型三唑并[4,3-a]吡啶衍生物的公式(I)，其中所有基团如权利要求中所定义。根据本发明的化合物是代谢型谷氨酸受体亚型2（"mGluR2"）的阳性变构调节剂，对于治疗或预防与谷氨酸功能障碍相关的神经和精神疾病以及代谢型受体的mGluR2亚型参与的疾病具有用处。本发明还涉及包括这种化合物的药物组合物，用于制备这种化合物和组合物的方法，以及利用这种化合物预防或治疗与mGluR2有关的神经和精神疾病和疾病。

  公开号：

  WO2010130422A1

文献信息

• 1,2,4-TRIAZOLO[4,3-a]PYRIDINE DERIVATIVES AND THEIR USE AS POSITIVE ALLOSTERIC MODULATORS OF MGLUR2 RECEPTORS
  申请人：Cic-Nunez Jose Maria

  公开号：US20120184527A1

  公开（公告）日：2012-07-19

  The present invention relates to novel triazolo[4,3-a]pyridine derivatives of Formula (I) wherein all radicals are as defined in the claims. The compounds according to the invention are positive allosteric modulators of the metabotropic glutamate receptor subtype 2 (“mGluR2”), which are useful for the treatment or prevention of neurological and psychiatric disorders associated with glutamate dysfunction and diseases in which the mGluR2 subtype of metabotropic receptors is involved. The invention is also directed to pharmaceutical compositions comprising such compounds, to processes to prepare such compounds and compositions, and to the use of such compounds for the prevention or treatment of neurological and psychiatric disorders and diseases in which mGluR2 is involved.

  本发明涉及式（I）的新型三唑并[4,3-a]吡啶衍生物，其中所有基团如权利要求所定义。根据本发明的化合物是代谢型谷氨酸受体亚型2（“mGluR2”）的正向异构调节剂，可用于治疗或预防与谷氨酸功能障碍相关的神经和精神障碍以及涉及代谢型受体亚型mGluR2的疾病。本发明还涉及包含这些化合物的制药组合物，制备这些化合物和组合物的方法，以及使用这些化合物预防或治疗涉及mGluR2的神经和精神障碍和疾病的用途。
• 1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mGluR2 receptors
  申请人：Cid-Nunez Jose Maria

  公开号：US08946205B2

  公开（公告）日：2015-02-03

  The present invention relates to novel triazolo[4,3-a]pyridine derivatives of Formula (I) wherein all radicals are as defined in the claims. The compounds according to the invention are positive allosteric modulators of the metabotropic glutamate receptor subtype 2 (“mGluR2”), which are useful for the treatment or prevention of neurological and psychiatric disorders associated with glutamate dysfunction and diseases in which the mGluR2 subtype of metabotropic receptors is involved. The invention is also directed to pharmaceutical compositions comprising such compounds, to processes to prepare such compounds and compositions, and to the use of such compounds for the prevention or treatment of neurological and psychiatric disorders and diseases in which mGluR2 is involved.

  本发明涉及一种新型三唑[4,3-a]吡啶衍生物（I式），其中所有基团如权利要求所定义。本发明的化合物是代谢性谷氨酸受体亚型2（“mGluR2”）的正向变构调节剂，可用于治疗或预防与谷氨酸功能紊乱相关的神经和精神障碍以及涉及代谢性受体的mGluR2亚型的疾病。本发明还涉及包含这种化合物的药物组合物，制备这种化合物和组合物的过程，以及使用这种化合物预防或治疗涉及mGluR2的神经和精神障碍和疾病。
• [EN] 1,2,4-TRIAZOLO[4,3-A]PYRIDINE DERIVATIVES AND THEIR USE AS POSITIVE ALLOSTERIC MODULATORS OF MGLUR2 RECEPTORS<br/>[FR] DÉRIVÉS DE LA 1,2,4-TRIAZOLO [4,3-A] PYRIDINE ET LEUR UTILISATION EN TANT QUE MODULATEURS ALLOSTÉRIQUES POSITIFS DES RÉCEPTEURS MGLUR2
  申请人：ORTHO MCNEIL JANSSEN PHARM

  公开号：WO2010130422A1

  公开（公告）日：2010-11-18

  The present invention relates to novel triazolo[4,3-a]pyridine derivatives of Formula (I) wherein all radicals are as defined in the claims. The compounds according to the invention are positive allosteric modulators of the metabotropic glutamate receptor subtype 2 ("mGluR2"), which are useful for the treatment or prevention of neurological and psychiatric disorders associated with glutamate dysfunction and diseases in which the mGluR2 subtype of metabotropic receptors is involved. The invention is also directed to pharmaceutical compositions comprising such compounds, to processes to prepare such compounds and compositions, and to the use of such compounds for the prevention or treatment of neurological and psychiatric disorders and diseases in which mGluR2 is involved.

  本发明涉及新型三唑并[4,3-a]吡啶衍生物的公式(I)，其中所有基团如权利要求中所定义。根据本发明的化合物是代谢型谷氨酸受体亚型2（"mGluR2"）的阳性变构调节剂，对于治疗或预防与谷氨酸功能障碍相关的神经和精神疾病以及代谢型受体的mGluR2亚型参与的疾病具有用处。本发明还涉及包括这种化合物的药物组合物，用于制备这种化合物和组合物的方法，以及利用这种化合物预防或治疗与mGluR2有关的神经和精神疾病和疾病。
• Imidazo[1,2-<i>a</i>]pyridines: Orally Active Positive Allosteric Modulators of the Metabotropic Glutamate 2 Receptor
  作者：Andrés A. Trabanco、Gary Tresadern、Gregor J. Macdonald、Juan Antonio Vega、Ana Isabel de Lucas、Encarnación Matesanz、Aránzazu García、María Lourdes Linares、Sergio A. Alonso de Diego、José Manuel Alonso、Daniel Oehlrich、Abdelah Ahnaou、Wilhelmus Drinkenburg、Claire Mackie、José Ignacio Andrés、Hilde Lavreysen、José María Cid

  DOI：10.1021/jm201561r

  日期：2012.3.22

  Advanced leads of an imidazopyridine series of positive allosteric modulators of the metabotropic glutamate 2 (mGlu2) receptor are reported. The optimization of in vitro ADMET and in vivo pharmacokinetic properties led to the identification of 27o. With good potency and selectivity for the mGlu2 receptor, 270 affected sleep-wake architecture in rats after oral treatment, which we have previously shown to be indicative of mGlu2 receptor-mediated central activity.