8-fluoro-2-methyl-quinolin-5-ol | 420786-80-7

• 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: 8-fluoro-2-methyl-quinolin-5-ol
• 英文别名: 8-Fluoro-2-methylquinolin-5-ol
• CAS: 420786-80-7
• 化学式: C₁₀H₈FNO
• 分子量: 177.178
• InChiKey: NQLZMZUHESIKLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-fluoro-2-methyl-quinolin-5-ol 在 吡啶 、 三氟甲磺酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以74%的产率得到8-fluoro-2-methyl-5-quinolinyl trifluoromethanesulfonate
  参考文献：
  名称：

  [EN] QUINOLINE AND QUINAZOLINE DERIVATIVES HAVING AFFINITY FOR 5HT1-TYPE RECEPTORS
  [FR] DERIVES DE QUINOLINE ET DE QUINAZOLINE PRESENTANT UNE AFFINITE VIS-A-VIS DES RECEPTEURS DU TYPE 5HT1

  摘要：

  提供了式(I)的化合物及其药用盐：其中R1、m、X、R2、n、W、p、Y、Z、R3、R4、R5和q的含义如描述中所定义。还公开了制备方法以及在治疗中的用途，特别是用于抑郁症或焦虑等中枢神经系统疾病。

  公开号：

  WO2005014552A1
• 作为产物：
  描述：

  8-fluoro-5-methoxy-2-methylquinoline 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 生成 8-fluoro-2-methyl-quinolin-5-ol
  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

• [EN] BENZOXAZINONE DERIVATIVES, PREPARATION THEREOF AND USES IN THE TREATMENT OF CNS AND OTHER DISORDERS<br/>[FR] DERIVES DE BENZOXAZINONE, PREPARATION DE CEUX-CI ET UTILISATIONS DE CEUX-CI DANS LE TRAITEMENT DE TROUBLES DU SNC ET D'AUTRES TROUBLES
  申请人：GLAXO GROUP LTD

  公开号：WO2004046124A1

  公开（公告）日：2004-06-03

  Compounds of formula (I) and pharmaceutically acceptable salts thereof are disclosed:wherein A, R1, R2, R3, p, q, A and X are as defined in the specification. Preparation of the compounds and uses in the treatment of CNS and other disorders, including depression and anxiety, are also disclosed.

  公开了化合物的公式(I)及其药用盐：其中A、R1、R2、R3、p、q、A和X的定义如规范中所述。还公开了化合物的制备方法以及在治疗中枢神经系统和其他疾病，包括抑郁症和焦虑症中的用途。
• Quinoline and quinazoline derivatives having affinity for 5ht1-type receptors
  申请人：Bergauer Markus

  公开号：US20060229312A1

  公开（公告）日：2006-10-12

  Compounds of formula (I) and pharmaceutically acceptable salts thereof are provided: wherein R 1 , m, X, R 2 , n, W, p, Y, Z, R 3 , R 4 , R 5 and q have the meanings as defined in the description. Methods of preparation and uses thereof in therapy, particularly for CNS disorders such as depression or anxiety, are also disclosed.

  提供式(I)的化合物和药学上可接受的盐：其中R1，m，X，R2，n，W，p，Y，Z，R3，R4，R5和q的含义如描述中所定义。还公开了制备方法以及在治疗中的用途，特别是用于中枢神经系统疾病，如抑郁症或焦虑症。
• Benzoxazinone derivatives, their preparation and use
  申请人：——

  公开号：US20040063704A1

  公开（公告）日：2004-04-01

  The present invention relates to novel compounds of formula (1) 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, C 1-6 alkyl, trifluoromethanesulfonyloxy, pentafluoroethyl, C 1-6 alkoxy, arylC 1-6 alkoxy, C 1-6 alkylthio, C 1-6 alkoxyC 1-6 -alkyl, C 3-7 cycloalkylC 1-6 alkoxy, C 1-6 alkanoyl, C 1-6 alkoxycarbonyl, C 1-6 alkylsulfonyl, C 1-6 alkylsulfinyl, C 1-6 alkylsulfonyloxy, C 1-6 alkylsulfonylC 1-6 alkyl, arylsulfonyl, arylsulfonyloxy, arylsulfonylC 1-6 alkyl, C 1-6 alkylsulfonamido, C 1-6 alkylamido, C 1-6 alkylsulfonamidoC 1-6 alkyl, C 1-6 alkylamidoC 1-6 alkyl, arylsulfonamido, arylcarboxamido, arylsullonamidoC 1-6 alkyl, arylcarboxamidoC 1-6 alkyl, aroyl, arylC 1-6 alkyl, arylC 1-6 alkanoyl, a group R 3 OCO(CH 2 ) s , R 3 CON(R 4 )(CH 2 ) s , R 3 R 4 NCO(C 2 ) s or R 3 R 4 NSO 2 (CH 2 ) where each of R 3 and R 4 independently represents a hydrogen atom or C 1-4 alkyl or R 3 and R 4 form part of a C 1-6 azacyloalkane or C 3- 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 phenyl or a monocyclic heteroaromatic group, said Ar 1 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, C 1-6 alkoxy or C 1-6 alkanoyl; when Ar is a phenyl or a monocyclic heteroaromatic group, substitutents positioned ortho to one another may be linked to form a 5- or 6-membered ring: R 1 is hydrogen, C 1-6 alkyl, C 3-6 alkenyl, C 3-6 alkynyl or arylC 1-6 alkyl; R 2 is halogen, C 1-6 alkyl, cyano, CF 3 , C 1-6 alkanoyl, C 1-6 alkoxy 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.

  本发明涉及公式（1）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，这些取代基可以相同或不同，选自以下群组：卤素，羟基，氰基，硝基，三氟甲基，三氟甲氧基，C1-6烷基，三氟甲磺酰氧基，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烷基亚磺基，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，芳基磺酰胺基C1-6烷基，芳基羧酰胺基C1-6烷基，酰基，芳基C1-6烷基，芳基C1-6酰基，一个R3OCO（CH2）s，R3CON（R4）（ ）s，R3R4NCO（C2）s或R3R4NSO2（ ）组，其中R3和R4各自独立地表示氢原子或C1-4烷基，或R3和R4构成C1-6氮杂环烷或C3-6（2-氧代）氮杂环烷环，s表示零或1-4的整数，以及一个Ar1Z基，其中Z表示单键，O，S或 ，Ar1表示苯基或单环杂芳基，所述Ar1基可以选择性地被1-3个取代基取代，这些取代基可以相同或不同，选自以下群组：卤素，羟基，氰基，三氟甲基，C1-6烷基，C1-6烷氧基或C1-6酰基；当Ar是苯基或单环杂芳基时，相对位于一个环上的取代基可以连接形成5-或6-成员环；R1是氢，C1-6烷基，C3-6烯基，C3-6炔基或芳基C1-6烷基；R2是卤素，C1-6烷基，氰基，CF3，C1-6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独立地为1或2。还公开了制备这些化合物的方法，包含它们的制药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。
• Benzoxazinone derivatives, preparation thereof and uses in the treatment of cns and other disorders
  申请人：Bertani Barbara

  公开号：US20060264429A1

  公开（公告）日：2006-11-23

  Compounds of formula (I) and pharmaceutically acceptable salts thereof are disclosed: wherein A, R1, R2, R3, p, q, A and X are as defined in the specification. Preparation of the compounds and uses in the treatment of CNS and other disorders, including depression and anxiety, are also disclosed.

  公开了化学式（I）的化合物及其药学上可接受的盐：其中A、R1、R2、R3、p、q、A和X的定义如规范中所述。还公开了这些化合物的制备方法以及在治疗中枢神经系统和其他疾病，包括抑郁和焦虑症方面的用途。
• Quinoline and quinazoline derivatives having affinity for 5HT1-type receptors
  申请人：Glaxo Group Limited

  公开号：US07279481B2

  公开（公告）日：2007-10-09

  Compounds of formula (I) and pharmaceutically acceptable salts thereof are provided: wherein R1, m, X, R2, n, W, p, Y, Z, R3, R4, R5 and q have the meanings as defined in the description. Methods of preparation and uses thereof in therapy, particularly for CNS disorders such as depression or anxiety, are also disclosed.

  提供化学式（I）的化合物及其药学上可接受的盐： 其中R1，m，X，R2，n，W，p，Y，Z，R3，R4，R5和q的含义如描述中所定义。还公开了其制备方法和在治疗中的用途，特别是用于中枢神经系统疾病，如抑郁症或焦虑症。