2-(4-chloropyridin-2-yl)-5-fluorobenzonitrile | 628323-61-5

• 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
• 英文名称: 2-(4-chloropyridin-2-yl)-5-fluorobenzonitrile
• CAS: 628323-61-5
• 化学式: C₁₂H₆ClFN₂
• 分子量: 232.644
• InChiKey: GZJSSJITMGYANL-UHFFFAOYSA-N

物化性质

• 沸点：
  374.2±42.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  36.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-chloropyridin-2-yl)-5-fluorobenzonitrile 、 3-Tributylstannanyl-7-trifluoromethyl-imidazo[1,2-a]pyrimidine 在 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 生成 5-Fluoro-2-[4-(7-trifluoromethyl-imidazo[1,2-a]pyrimidin-3-yl)-pyridin-2-yl]-benzonitrile
  参考文献：
  名称：

  Imidazo[1,2-a]pyrimidines as functionally selective GABAA ligands

  摘要：

  Imidazo[1,2-a]pyrimidines are GABA(A) receptor benzodiazepine binding site ligands which can exhibit functional selectivity for the alpha(3) subtype over the alpha(1) subtype. SAR studies to optimize this functional selectivity are described. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.11.112
• 作为产物：
  描述：

  B-(2-氰基-4-氟苯基)-硼酸 、 2,4-二氯吡啶 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 sodium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 以38%的产率得到2-(4-chloropyridin-2-yl)-5-fluorobenzonitrile
  参考文献：
  名称：

  Imidazo[1,2-a]pyrimidines as functionally selective GABAA ligands

  摘要：

  Imidazo[1,2-a]pyrimidines are GABA(A) receptor benzodiazepine binding site ligands which can exhibit functional selectivity for the alpha(3) subtype over the alpha(1) subtype. SAR studies to optimize this functional selectivity are described. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.11.112

文献信息

• [EN] 5,8-DIFLUOROIMIDAZO[1,2-a]PYRIDINES AS GABA-A alpha2/alpha3 LIGANDS FOR TREATING ANXIETY AND/OR DEPRESSION<br/>[FR] 5,8-DIFLUOROIMIDAZO[1,2-A]PYRIDINES CONSTITUANT DES LIGANDS GABA-A <2/?3 UTILISES DANS LE TRAITEMENT DE L'ANXIETE ET/OU DE LA DEPRESSION
  申请人：MERCK SHARP & DOHME

  公开号：WO2004076452A1

  公开（公告）日：2004-09-10

  The present invention provides a compound of formula I: wherein W is a five- or six-membered optionally substituted heteroaromatic ring; or optionally substituted phenyl, substituted meta to the imidazopyridine core by Y-Z where: Y represents a chemical bond, an oxygen atom, or a -NH- linkage; and Z represents aryl, heteroaryl or pyridin-2-on-1-yl, any of which groups may be optionally substituted; R1 represents hydrogen, hydrocarbon, a heterocyclic group, halogen, cyano, trifluoromethyl, nitro, -ORa, -SRa, -SORa, -SO2Ra, -SO2NRaRb, NRaRb, -NRaCORb, -NRaCO2Rb, -CORa, -CO2Ra, -CONRaRb or -CRa=NORb; and Ra and Rb independently represent hydrogen, hydrocarbon or a heterocyclic group; pharmaceutical compositions comprising it, its use in therapy; and use of it to treat or prevent anxiety or depression.

  本发明提供了一种式I的化合物：其中W是一个五元或六元的可选择替代的杂芳环；或者是可选择替代的苯基，通过Y-Z取代到咪唑吡啶核心的meta位，其中：Y代表化学键，氧原子，或-NH-连接；Z代表芳基，杂芳基或吡啶-2-酮-1-基，其中任何这些基团都可以选择性地被取代；R1代表氢，碳氢化合物，杂环基团，卤素，氰基，三氟甲基，硝基，-ORa，-SRa，-SORa，-SO2Ra，-SO2NRaRb，NRaRb，-NRaCORb，-NRaCO2Rb，-CORa，-CO2Ra，-CONRaRb或-CRa=NORb；Ra和Rb独立地代表氢，碳氢化合物或杂环基团；包括它的药物组合物，它在治疗中的应用；以及将其用于治疗或预防焦虑或抑郁的用途。
• [EN] 8-FLUORIMIDAZO`1,2-A!PYRIDINE DERIVATIVES AS LIGANDS FOR GABA RECEPTORS<br/>[FR] DERIVES DE 8-FLUORIMIDAZO[1,2- DOLLAR G(A)]PYRIDINE UTILISES COMME LIGANDS POUR LES RECEPTEURS GABA
  申请人：MERCK SHARP & DOHME

  公开号：WO2003099817A1

  公开（公告）日：2003-12-04

  A class of 8-fluoroimidazo[1,2-a]pyridine derivatives, substituted at the 3-position by an optionally substituted five-membered or six-membered heteroaromatic ring, being selective ligands for GABAA receptors, in particular having high affinity for the α2 and/or α3 and/or α5 subunit thereof, are accordingly of benefit in the treatment and/or prevention of adverse conditions of the central nervous system, including anxiety, convulsions and cognitive disorders.

  一类8-氟咪唑[1,2-a]吡啶衍生物，取代在3位处的五元或六元杂芳环，作为GABAA受体的选择性配体，特别具有高亲和力的α2和/或α3和/或α5亚基，因此在治疗和/或预防中枢神经系统的不良状况，包括焦虑、抽搐和认知障碍方面具有益处。
• 8-Fluoroimidazo 1,2-a pyridine derivatives as ligands for gaba receptors
  申请人：Blackaby Peter Wesley

  公开号：US20060052385A1

  公开（公告）日：2006-03-09

  A class of 8-fluoroimidazo[1,2-α]pyridine derivatives, substituted at the 3-position by an optionally substituted five-membered or six-membered heteroaromatic ring, being selective ligands for GABA A receptors, in particular having high affinity for the α2 and/or α3 and/or α5 subunit thereof, are accordingly of benefit in the treatment and/or prevention of adverse conditions of the central nervous system, including anxiety, convulsions and cognitive disorders.

  一类8-氟咪唑[1,2-α]吡啶衍生物，它们在3-位被一个可选择取代的五元或六元杂环芳香环所取代，是GABAA受体的选择性配体，特别是对α2和/或α3和/或α5亚单位具有高亲和力，因此对于治疗和/或预防中枢神经系统的不良症状，包括焦虑、抽搐和认知障碍具有益处。
• 8-fluoroimidazo 1,2-a pyridine derivatives as ligands for GABA receptors
  申请人：Merck Sharp & Dohme Ltd.

  公开号：US07226926B2

  公开（公告）日：2007-06-05

  A class of 8-fluoroimidazo[1,2-α]pyridine derivatives, substituted at the 3-position by an optionally substituted five-membered or six-membered heteroaromatic ring, being selective ligands for GABAA receptors, in particular having high affinity for the α2 and/or α3 and/or α5 subunit thereof, are accordingly of benefit in the treatment and/or prevention of adverse conditions of the central nervous system, including anxiety, convulsions and cognitive disorders.

  一类8-氟咪唑[1,2-α]吡啶衍生物，在3位被一个可选择取代的五元或六元杂环芳香环取代，成为GABAA受体的选择性配体，特别是对其中的α2和/或α3和/或α5亚单位具有高亲和力，因此有助于治疗和/或预防中枢神经系统的不良状况，包括焦虑、惊厥和认知障碍。
• 8-FLUORIMIDAZO(1,2-A)PYRIDINE DERIVATIVES AS LIGANDS FOR GABA RECEPTORS
  申请人：MERCK SHARP & DOHME LTD.

  公开号：EP1511748A1

  公开（公告）日：2005-03-09