5-(2,2,2-trifluoroethyl)picolinic acid

• 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: 5-(2,2,2-trifluoroethyl)picolinic acid
• 英文别名: 2-Pyridinecarboxylic acid, 5-(2,2,2-trifluoroethyl)-；5-(2,2,2-trifluoroethyl)pyridine-2-carboxylic acid
• 化学式: C₈H₆F₃NO₂
• 分子量: 205.136
• InChiKey: KXQZLPJUICJJFY-UHFFFAOYSA-N

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：
  0.25
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-溴-5-醛基吡啶 在 盐酸 、 硫酸 、 palladium 10% on activated carbon 、 水 、 氢气 、 三乙胺 、 四丁基二氟三苯硅酸铵 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， -78.0~120.0 ℃ 、101.33 kPa 条件下， 反应 35.33h， 生成 5-(2,2,2-trifluoroethyl)picolinic acid
  参考文献：
  名称：

  Iminothiadiazine Dioxide Compounds as BACE Inhibitors, Compositions and Their Use

  摘要：

  本发明提供了多种形式的亚氨基噻二唑二氧化物化合物，包括公式(I)的化合物： 包括它们的立体异构体，以及所述立体异构体的药用可接受盐，其中R1、R2、R3、R4、R5、R9、环A、环B、m、n、p、-L1-、-L2-和-L3-都是独立选择且按本文定义。发明的新型亚氨基噻二唑二氧化物化合物出人意料地被发现具有预期的特性，使其作为BACE抑制剂以及/或用于治疗和预防与β-淀粉样蛋白（“Aβ”）生成相关的各种病理学具有优势。还公开了包含一个或多个此类化合物（单独使用和与一个或多个其他活性成分组合使用）的药物组合物，以及它们的制备方法和用于治疗与淀粉样β（Aβ）蛋白相关的病理学，包括阿尔茨海默病的方法。

  公开号：

  US20150307465A1

文献信息

• [EN] IMINOTHIADIAZINE DIOXIDE COMPOUNDS AS BACE INHIBITORS, COMPOSITIONS, AND THEIR USE<br/>[FR] COMPOSÉS DE DIOXYDE D'IMINOTHIADIAZINE COMME INHIBITEURS DE BACE, COMPOSITIONS ET LEUR UTILISATION
  申请人：SCHERING CORP

  公开号：WO2011044181A1

  公开（公告）日：2011-04-14

  In its many embodiments, the present invention provides certain iminothiadiazine dioxide compounds, including compounds Formula (I): (I) and include stereoisomers thereof, and pharmaceutically acceptable salts of said compounds stereoisomers, wherein each of R1, R2, R3, R4, R5, R9, ring A, ring B, m, n, p, -L1-,L2-, and L3- is selected independently and as defined herein. The novel iminothiadiazine dioxide compounds of the invention have surprisingly been found to exhibit properties which are expected to render them advantageous as BACE inhibitors and/or for the treatment and prevention of various pathologies related to β-amyloid (Aβ) production. Pharmaceutical compositions comprising one or more such compounds (alone and in combination with one or more other active agents), and methods for their preparation and use in treating pathologies associated with amyloid beta (Aβ) protein, including Alzheimers disease, are also disclosed.

  在其多种实施方式中，本发明提供了某些亚氨基噻二嗪二氧化物化合物，包括化合物式(I)的化合物和其立体异构体，以及所述化合物立体异构体的药学上可接受的盐，其中每个R1、R2、R3、R4、R5、R9、环A、环B、m、n、p、-L1-、L2-和L3-都是独立选择并在此定义。该发明的新型亚氨基噻二嗪二氧化物化合物出人意料地表现出具有优势的BACE抑制剂特性和/或用于治疗和预防与β-淀粉样蛋白（Aβ）产生相关的各种病理的特性。还公开了包括一种或多种这样的化合物（单独和与一种或多种其他活性剂的组合）的制药组合物，并揭示了在治疗与淀粉样β（Aβ）蛋白相关的病理，包括阿尔茨海默病中使用它们的方法。
• IMINOTHIADIAZINE DIOXIDE COMPOUNDS AS BACE INHIBITORS, COMPOSITIONS AND THEIR USE
  申请人：Scott Jack D.

  公开号：US20120183563A1

  公开（公告）日：2012-07-19

  In its many embodiments, the present invention provides certain iminothiadiazine dioxide compounds, including compounds Formula (I): (I) and include stereoisomers thereof, and pharmaceutically acceptable salts of said compounds stereoisomers, wherein each of R 1 , R 2 , R 3 , R 4 , R 5 , R 9 , ring A, ring B, m, n, p, -L 1 -,L 2 -, and L 3 - is selected independently and as defined herein. The novel iminothiadiazine dioxide compounds of the invention have surprisingly been found to exhibit properties which are expected to render them advantageous as BACE inhibitors and/or for the treatment and prevention of various pathologies related to β-amyloid (Aβ) production. Pharmaceutical compositions comprising one or more such compounds (alone and in combination with one or more other active agents), and methods for their preparation and use in treating pathologies associated with amyloid beta (Aβ) protein, including Alzheimers disease, are also disclosed.

  在其多种实施方式中，本发明提供了某些亚硫酰二氮杂环化合物，包括化合物式（I）：（I）及其立体异构体和所述化合物立体异构体的药学上可接受的盐，其中R1、R2、R3、R4、R5、R9、环A、环B、m、n、p、-L1-、L2-和L3-各自独立选择并如所定义。本发明的新型亚硫酰二氮杂环化合物出人意料地表现出预期的性质，使它们作为BACE抑制剂和/或用于治疗和预防与β-淀粉样蛋白（Aβ）产生相关的各种病理学具有优势。还公开了包括一种或多种这样的化合物（单独和与一种或多种其他活性剂的组合）的制药组合物，以及用于治疗与淀粉样β（Aβ）蛋白相关的病理学，包括阿尔茨海默病的方法。
• IMINOTHIADIAZINE DIOXIDE COMPOUNDS AS BACE INHIBITORS, COMPOSITIONS, AND THEIR USE
  申请人：Scott Jack D.

  公开号：US20140296221A1

  公开（公告）日：2014-10-02

  In its many embodiments, the present invention provides certain iminothiadiazine dioxide compounds, including compounds Formula (I): and include stereoisomers thereof, and pharmaceutically acceptable salts of said compounds stereoisomers, wherein each of R 1 , R 2 , R 3 , R 4 , R 5 , R 9 , ring A, ring B, m, n, p, -L 1 -, -L 2 -, and -L 3 - is selected independently and as defined herein. The novel iminothiadiazine dioxide compounds of the invention have surprisingly been found to exhibit properties which are expected to render them advantageous as BACE inhibitors and/or for the treatment and prevention of various pathologies related to β-amyloid (“Aβ”) production. Pharmaceutical compositions comprising one or more such compounds (alone and in combination with one or more other active agents), and methods for their preparation and use in treating pathologies associated with amyloid beta (Aβ) protein, including Alzheimer's disease, are also disclosed.

  在其多种实施方式中，本发明提供了某些亚氨基噻二嗪二氧化物化合物，包括化合物公式（I）的化合物：以及其立体异构体和该化合物立体异构体的药学上可接受的盐，其中每个R1、R2、R3、R4、R5、R9、环A、环B、m、n、p、-L1-、-L2-和-L3-独立选择并在此定义。本发明的新型亚氨基噻二嗪二氧化物化合物出乎意料地表现出有利于作为BACE抑制剂和/或用于治疗和预防与β-淀粉样蛋白（“Aβ”）产生相关的各种病理的性质。还公开了包括一个或多个此类化合物（单独和与一个或多个其他活性剂的组合）的制药组合物，以及用于治疗与淀粉样β（Aβ）蛋白相关的病理，包括阿尔茨海默病的制备和使用方法。
• 2-Substituted-5-trifluoromethylpyridines and a process for producing the same
  申请人：ISHIHARA SANGYO KAISHA LTD.

  公开号：EP0034917A1

  公开（公告）日：1981-09-02

  A 2-substituted-5-trifluoromethylpyridine compound is represented bytheformula (I) wherein X is a hydrogen atom or a halogen atom, and Y is a cyano group or a carboxy group, provided that when Y is a cyanogroup then X is a halogenatom; orasaltthereof. When Y is a carboxy group, the compound of formulae) is prepared by reacting a 2-bromo-5-trifluoromethylpyridine represented by the formula (IV). wherein X is the same as defined above, with carbon dioxide in a solvent, in the presence of an organometallic compound, and in an inert gas atmosphere. When Y is a cyano group and X is a halogen atom, the compound of formula (I) is prepared by reacting a 2-bromo-5-trifluoromethylpyridine represented by the formula (IV'): wherein Hal is the halogen atom, with a cyanating agent. The compound of formula (I) is useful as an intermediate in the production of insecticides.

  一种 2-取代的-5-三氟甲基吡啶化合物由式(I)表示 其中 X 为氢原子或卤素原子，Y 为氰基或羧基，但当 Y 为氰基时，X 为卤素原子；或与之相同。 当 Y 为羧基时，式）化合物是通过与式 (IV) 所代表的 2-溴-5-三氟甲基吡啶反应制备的。 其中 X 与上述定义相同，在溶剂中、有机金属化合物存在下和惰性气体环境中与二氧化碳反应。 当 Y 为氰基，X 为卤素原子时，式（I）化合物通过与式 (IV') 所代表的 2-溴-5-三氟甲基吡啶反应制备： 其中 Hal 为卤原子，与氰化剂反应。 式（I）化合物可用作生产杀虫剂的中间体。
• US8729071B2
  申请人：——

  公开号：US8729071B2

  公开（公告）日：2014-05-20