6-Fluoro-5-methoxy-2-methylquinoline | 420786-94-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 6-Fluoro-5-methoxy-2-methylquinoline
• CAS: 420786-94-3
• 化学式: C₁₁H₁₀FNO
• 分子量: 191.205
• InChiKey: KIICZXRAQUDSFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-Fluoro-5-methoxy-2-methylquinoline 在 二氯甲烷 、 碳酸氢钠 、 Sodium sulfate-III 作用下， 以 氢溴酸 为溶剂， 反应 24.0h， 以to give the title compound as a brown solid (1.39 g, 73%)的产率得到6-氟-2-甲基-5-喹啉醇
  参考文献：
  名称：

  Benzoxazinone derivatives, their preparation and use

  摘要：

  本发明涉及公式（I）的新化合物或其药学上可接受的盐，其中Ar是苯基、萘基、单环杂芳基或双环杂芳基，所述Ar基可以选择性地被1-4个取代基取代，所述取代基可以是相同的或不同的，所述取代基选择自卤素、羟基、氰基、硝基、三氟甲基、三氟甲氧基、C1-6烷基、三氟甲烷基磺酰氧基、五氟乙基、C1-6烷氧基、芳基C1-6烷氧基、C1-6烷硫基、C1-6烷氧基C1-6烷基、C3-7环烷基C1-6烷氧基、C1-6酰基、C1-6烷氧羰基、C1-6烷基磺酰基、C1-6烷基亚砜基、C1-6烷基磺酰氧基、C1-6烷基磺酰基C1-6烷基、芳基磺酰基、芳基磺酰氧基、芳基磺酰基C1-6烷基、C1-6烷基磺酰胺基、C1-6烷基酰胺基、C1-6烷基磺酰胺基C1-6烷基、C1-6烷基酰胺基C1-6烷基、芳基磺酰胺基、芳基羧酰胺基、烷基磺酰胺基C1-6烷基、芳基羧酰胺基C1-6烷基、芳基羰基、芳基C1-6烷基、芳基C1-6烷酰基、一组R <3>OCO（CH2）s，R <3>CON（R <4>）（CH2）s，R <3>R <4>NCO（CH2）s或R <3>R <4>NSO2（CH2），其中R <3>和R <4>各自独立地表示氢原子或C1-4烷基，或R <3>和R <4>形成C3-6杂氮环烷或C3-6（2-氧代）杂氮环烷环的一部分，s表示0或1-4的整数，以及一组Ar <1> Z，其中Z表示单键，O，S或CH2，Ar <1>表示苯基或单环杂芳基，所述Ar <1>基可以选择性地被1-3个取代基取代，所述取代基可以是相同的或不同的，所述取代基选择自卤素、羟基、氰基、三氟甲基、C1-6烷基、C1-6烷氧基或C1-6烷酰基；当Ar是苯基或单环杂芳基时，相对位于取代基可以连接成5-或6-成员环；R <1>是氢、C1-6烷基、C3-6烯基、C3-6炔基或芳基C1-6烷基；R <2>是卤素、C1-6烷基、氰基、CF3、C1-6烷酰基、C1-6烷氧基或羟基；X是CH或N；Y是单键、O或C═O；p是0、1或2；r是0、1、2或3；m是2、3或4；n和q分别为1或2。还公开了制备这些化合物的方法，包含它们的药物组合物以及它们作为治疗各种中枢神经系统疾病，包括抑郁和/或焦虑的药物的用途。

  公开号：

  US06939871B2
• 作为产物：
  描述：

  2-溴-4-氟-5-甲氧基苯胺 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 为溶剂， 生成 6-Fluoro-5-methoxy-2-methylquinoline
  参考文献：
  名称：

  3,4-Dihydro-2H-benzoxazinones as dual-acting 5-HT1A receptor antagonists and serotonin reuptake inhibitors

  摘要：

  Investigation of halogen substitution in lead compound 1 has led to the identification of analogues which combine high affinity for 5-HT1A receptors and potent serotonin reuptake inhibitory activity. Several compounds show an improved selectivity over 5-HT1B and 5-HT1D receptors and a superior pharmacokinetic profile in the rat. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.11.031

文献信息

• BENZOXAZINONE DERIVATIVES, THEIR PREPARATION AND USE
  申请人：SMITHKLINE BEECHAM PLC

  公开号：EP1330460B1

  公开（公告）日：2007-03-21
• US6939871B2
  申请人：——

  公开号：US6939871B2

  公开（公告）日：2005-09-06
• [EN] BENZOXAZINONE DERIVATIVES, THEIR PREPARATION AND USE<br/>[FR] DERIVES DE BENZOXAZINONE, LEUR PREPARATION ET UTILISATION
  申请人：SMITHKLINE BEECHAM PLC

  公开号：WO2002034754A2

  公开（公告）日：2002-05-02

  The present invention relates to novel compounds of formula (I) or a pharmaceutically acceptable salt thereof, wherein Ar is phenyl, naphthyl, a monocyclic heteroaromatic group or a bicyclic heteroaromatic group, said Ar group being optionally substituted by 1-4 substituents, which may be the same or different, and which are selected from the group consisting of: halogen, hydroxy, cyano, nitro, trifluoromethyl, trifluoromethoxy, C1-6alkyl, trifluoromethanesulfonyloxy, pentafluoroethyl, C1-6alkoxy, arylC1-6alkoxy, C1-6alkylthio, C1-6alkoxyC1-6alkyl, C3-7cycloalkylC1-6alkoxy, C1-6alkanoyl, C1-6alkoxycarbonyl, C1-6alkylsulfonyl, C1-6alkylsulfinyl, C1-6alkylsulfonyloxy, C1-6alkylsulfonylC1-6alkyl, arylsulfonyl, arylsulfonyloxy, arylsulfonylC1-6alkyl, C1-6alkylsulfonamido, C1-6alkylamido, C1-6alkylsulfonamidoC1-6alkyl, C1-6alkylamidoC1-6alkyl, arylsulfonamido, arylcarboxamido, arylsulfonamidoC1-6alkyl, arylcarboxamidoC1-6alkyl, aroyl, aroylC1-6alkyl, arylC1-6alkanoyl, a group R3OCO(CH¿2?)s, R?3CON(R4)(CH¿2)s, R3R4NCO(CH¿2?)s or R?3R4NSO¿2(CH2) where each of R?3 and R4¿ independently represents a hydrogen atom or C¿1-4?alkyl or R?3 and R4¿ form part of a C¿3-?6azacyloalkane or C3-6(2-oxo)azacycloalkane ring and s represents zero or an integer from 1 to 4, and a group Ar?1¿ Z, wherein Z represents a single bond, O, S or CH¿2? and Ar?1¿ represents a pheyl or a monocyclic heteroaromatic group, said Ar1 group being optionally substituted by 1-3 substituents, which may be the same or different, and which are selected from the group consisting of a halogen, hydroxy, cyano, trifluoromethyl, C¿1-6?alkyl, C1-6alkoxy or C1-6alkanoyl; when Ar is a phenyl or a monocyclic heteroaromatic group, substitutens positioned ortho to one another may be linked to form a 5- or 6-membered ring; R?1¿ is hydrogen, C¿1-6?alkyl, C3-6alkenyl, C3-6alkynyl or arylC1-6alkyl; R?2¿ is halogen, C¿1-6?alkyl, cyano, CF3, C1-6alkanoyl, C1-6alkoxy or hydroxy; X is CH or N; Y is a single bond, O, or C=O; p is 0, 1 or 2; r is 0, 1, 2 or 3; m is 2, 3 or 4; n and q are independently 1 or 2. Processes for preparing the compounds, pharmaceutical compositions containing them and their use as medicaments for various CNS disorders, including deression and/or anxiety, are also disclosed.