5-溴-N-叔丁基吡啶-2-甲酰胺 | 647826-69-5

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 5-溴-N-叔丁基吡啶-2-甲酰胺
• 英文名称: 5-bromo-pyridine-2-carboxylic acid tert-butylamide
• 英文别名: 2-Pyridinecarboxamide, 5-bromo-N-(1,1-dimethylethyl)-；5-bromo-N-tert-butylpyridine-2-carboxamide
• CAS: 647826-69-5
• 化学式: C₁₀H₁₃BrN₂O
• 分子量: 257.13
• InChiKey: CSHMSFDZSULBAW-UHFFFAOYSA-N

物化性质

• 沸点：
  361.4±27.0 °C(Predicted)
• 密度：
  1.362±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-溴-N-叔丁基吡啶-2-甲酰胺 在 三氯氧磷 作用下， 以 甲苯 为溶剂， 反应 5.0h， 生成 5-溴-2-氰基吡啶
  参考文献：
  名称：

  An Efficient Synthesis of 5-Bromopyridine-2-carbonitrile

  摘要：

  5-Bromopyridine-2-carbonitrile was efficiently synthesized in two steps from 2,5-dibromopyridine with an overall yield of 75%.

  DOI：

  10.1081/scc-120023985
• 作为产物：
  描述：

  5-溴-2-吡啶羧酸 、 叔丁胺 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 16.0h， 以92%的产率得到5-溴-N-叔丁基吡啶-2-甲酰胺
  参考文献：
  名称：

  [EN] ETHYNYL DERIVATIVES AS MODULATORS OF MGLUR5 RECEPTOR ACTIVITY
  [FR] DÉRIVÉS D'ÉTHYNYLE COMME MODULATEURS DE L'ACTIVITÉ DU RÉCEPTEUR MGLUR5

  摘要：

  本发明涉及公式(I)的乙炔衍生物或药学上可接受的酸盐，或其相应的外消旋混合物，或其对映体和/或光学异构体和/或立体异构体。令人惊讶地发现，通式(I)的化合物是代谢型谷氨酸受体拮抗剂（负向变构调节剂），用于治疗焦虑和疼痛、抑郁症、脆性X综合征、自闭症谱系障碍、帕金森病和胃食管反流病（GERD）。

  公开号：

  WO2014060394A1

文献信息

• PHENYL OR PYRIDINYL-ETHYNYL DERIVATIVES
  申请人：Jaeschke Georg

  公开号：US20120270852A1

  公开（公告）日：2012-10-25

  The present invention relates to ethynyl derivatives of formula I wherein Y is N or C—R 3 ; R 3 is hydrogen, methyl, halogen or nitrile; R 1 is phenyl or pyridinyl, each of which is optionally substituted by halogen, lower alkyl or lower alkoxy; R 2 /R 2′ are each independently hydrogen, lower alkyl or lower alkyl substituted by halogen, or R 2 and R 2′ together with the N-atom to which they are attached form a morpholine ring, a piperidine ring or an azetidine ring, each of which is unsubstituted or substituted one or more substituents selected from lower alkoxy, halogen, hydroxy and methyl; R 4 /R 4′ are each independently hydrogen or lower alkyl, or R 4 and R 4′ together form a C 3-5 cycloalkyl-, tetrahydrofuran- or an oxetane-ring; or to a pharmaceutically acceptable acid addition salt, to a racemic mixture, or to its corresponding enantiomer and/or optical isomer and/or stereoisomer thereof. Compounds of formula I are positive allosteric modulators (PAM) of the metabotropic glutamate receptor subtype 5 (mGluR5).

  本发明涉及公式I的乙炔衍生物，其中Y为N或C—R3；R3为氢、甲基、卤素或腈基；R1为苯基或吡啶基，每个基团可选择地被卤素、低烷基或低烷氧基取代；R2/R2′各自独立地为氢、低烷基或被卤素取代的低烷基，或者R2和R2′与它们连接的N原子一起形成一个吗啉环、哌啶环或氮杂环，每个环未取代或取代一个或多个从低烷氧基、卤素、羟基和甲基中选取的取代基；R4/R4′各自独立地为氢或低烷基，或者R4和R4′一起形成一个C3-5环烷基、四氢呋喃环或噁唑环；或者形成药用可接受的酸盐、对映体混合物，或其对应的对映体和/或光学异构体和/或立体异构体。公式I的化合物是代谢型谷氨酸受体亚型5（mGluR5）的正向变构调节子（PAM）。
• [EN] 5-(PHENYL/PYRIDINYL-ETHINYL)-2-PYRIDINE/ 2-PYRIMIDINE-CARBORXAMIDES AS MGLUR5 MODULATORS<br/>[FR] 5-(PHÉNYL/PYRIDINYL-ÉTHINYL)-2-PYRIDINE/2 PYRIMIDINE-CARBOXAMIDES COMME MODULATEUR DE MGLUR5
  申请人：HOFFMANN LA ROCHE

  公开号：WO2012143340A1

  公开（公告）日：2012-10-26

  The present invention relates to ethynyl derivatives of formula (I), wherein, Y is N or C-R3;and R3 is hydrogen, methyl, halogen or nitrile; R1 is phenyl or pyridinyl, which are optionally substituted by halogen, lower alkyl or lower alkoxy; R2/R2' are independently from each other hydrogen, lower alkyl or lower alkyl substituted by halogen, or R2 and R2' may form together with the N-atom to which they are attached a morpholine ring, a piperidine ring or an azetidine ring, which are unsubstituted or substituted one or more substituents selected from lower alkoxy, halogen, hydroxy or methyl; R4/R4' are independently from each other hydrogen or lower alkyl, or R4 and R4' form together a C3-5 cycloalkyl-, tetrahydrofuran- or an oxetane-ring; or to a pharmaceutically acceptable acid addition salt, to a racemic mixture, or to its corresponding enantiomer and/or optical isomer and/or stereoisomer thereof. It has now surprisingly been found that the compounds of general formula (I) are positive allosteric modulators (PAM) of the metabotropic glutamate receptor subtype 5 (mGluR5).

  本发明涉及公式（I）的乙炔衍生物，其中，Y是N或C-R3；R3是氢、甲基、卤素或腈基；R1是苯基或吡啶基，可以选择地被卤素、低烷基或低烷氧基取代；R2/R2'分别是氢、低烷基或被卤素取代的低烷基，或者R2和R2'可以与它们连接的N原子一起形成吗啡啉环、哌啶环或氮杂环，该环未被取代或被一个或多个从低烷氧基、卤素、羟基或甲基中选择的取代基取代；R4/R4'分别是氢或低烷基，或者R4和R4'一起形成C3-5环烷基、四氢呋喃环或氧杂环；或者是药学上可接受的酸盐，或者是消旋混合物，或者是其对应的对映体和/或光学异构体和/或立体异构体。令人惊讶的是发现，通用公式（I）的化合物是代谢型谷氨酸受体亚型5（mGluR5）的阳性变构调节剂（PAM）。
• Phenyl or pyridinyl-ethynyl derivatives
  申请人：Jaeschke Georg

  公开号：US08772300B2

  公开（公告）日：2014-07-08

  The present invention relates to ethynyl derivatives of formula I wherein Y is N or C—R3; R3 is hydrogen, methyl, halogen or nitrile; R1 is phenyl or pyridinyl, each of which is optionally substituted by halogen, lower alkyl or lower alkoxy; R2/R2′ are each independently hydrogen, lower alkyl or lower alkyl substituted by halogen, or R2 and R2′ together with the N-atom to which they are attached form a morpholine ring, a piperidine ring or an azetidine ring, each of which is unsubstituted or substituted one or more substituents selected from lower alkoxy, halogen, hydroxy and methyl; R4/R4′ are each independently hydrogen or lower alkyl, or R4 and R4′ together form a C3-5 cycloalkyl-, tetrahydrofuran- or an oxetane-ring; or to a pharmaceutically acceptable acid addition salt, to a racemic mixture, or to its corresponding enantiomer and/or optical isomer and/or stereoisomer thereof. Compounds of formula I are positive allosteric modulators (PAM) of the metabotropic glutamate receptor subtype 5 (mGluR5).

  本发明涉及公式I的乙炔衍生物，其中Y为N或C—R3；R3为氢，甲基，卤素或腈基；R1为苯基或吡啶基，每个基团可以选择性地被卤素，低碳基或低碳氧基取代；R2/R2'各自独立地为氢，低碳基或被卤素取代的低碳基，或者R2和R2'与它们所连接的N原子一起形成一个吗啡环，哌啶环或氮杂环，每个基团可以是未取代的或取代了一个或多个来自低碳氧基，卤素，羟基和甲基的取代基；R4/R4'各自独立地为氢或低碳基，或者R4和R4'一起形成一个C3-5环烷基，四氢呋喃基或氧杂环，或者其对应的内消旋体和/或光学异构体和/或立体异构体的药学上可接受的酸盐。公式I的化合物是代谢型谷氨酸受体亚型5（mGluR5）的正向变构调节剂（PAM）。
• Ethynyl Derivatives
  申请人：Hoffmann-La Roche Inc.

  公开号：US20150225344A1

  公开（公告）日：2015-08-13

  The present invention relates to ethynyl derivatives of formula I wherein Y is N or CH or to a pharmaceutically acceptable acid addition salt, to a racemic mixture, or to its corresponding enantiomer and/or optical isomer and/or stereoisomer thereof. It has now surprisingly been found that the compounds of general formula I are metabotropic glutamate receptor antagonists (negative allosteric modulators) for use in the treatment of anxiety and pain, depression, Fragile-X syndrome, autism spectrum disorders, Parkinson's disease, and gastroesophageal reflux disease (GERD).

  本发明涉及公式I的乙炔衍生物，其中Y为N或CH，或其药学上可接受的酸加成盐，或其相应的外消旋体混合物，或其对映体和/或光学异构体和/或立体异构体。现已惊奇地发现，通式I化合物是代谢型谷氨酸受体拮抗剂（负向变构调节剂），用于治疗焦虑和疼痛、抑郁症、脆性X综合症、自闭症谱系障碍、帕金森病和胃食管反流病（GERD）。
• Ethynyl derivatives
  申请人：Hoffmann-La Roche Inc.

  公开号：US09328070B2

  公开（公告）日：2016-05-03

  The present invention relates to ethynyl derivatives of formula I wherein Y is N or CH or to a pharmaceutically acceptable acid addition salt, to a racemic mixture, or to its corresponding enantiomer and/or optical isomer and/or stereoisomer thereof.

  本发明涉及公式I的乙炔衍生物，其中Y是N或CH，以及其药学上可接受的酸加成盐，外消旋混合物或其相应的对映体和/或光学异构体和/或立体异构体。