2-(tert-butylamino)-3,5,6-trifluoropyridine

• 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-(tert-butylamino)-3,5,6-trifluoropyridine
• 英文别名: 2-(t-butylamino)-3,5,6-trifluoropyridine；N-(tert-butyl)-3,5,6-trifluoropyridin-2-amine；N-tert-butyl-3,5,6-trifluoropyridin-2-amine
• 化学式: C₉H₁₁F₃N₂
• 分子量: 204.195
• InChiKey: TYMKLKWMUMXYKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  24.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(tert-butylamino)-3,5,6-trifluoropyridine 在 盐酸 、 palladium 10% on activated carbon 、 氢气 作用下， 以 N-甲基吡咯烷酮 、 甲醇 、 水 为溶剂， 反应 48.0h， 生成 2-amino-6-tert-butylamino-3,5-diflouropyridine
  参考文献：
  名称：

  Discovery of WQ-3810: Design, synthesis, and evaluation of 7-(3-alkylaminoazetidin-1-yl)fluoro-quinolones as orally active antibacterial agents

  摘要：

  Novel 7-(3-allcylaminoazetidin-1-yl)fluoroquinolones were designed, synthesized, and evaluated for their antibacterial activities and oral absorption rates. Against Gram-negative bacteria, 10a-e, which have various alkyl groups containing different numbers of carbon atoms (C0-C3) at the C-7 alkylaminoazetidine position, showed potent and similar antibacterial activities, whereas the activity of 10f (C4, t-Bu) was significantly lower than those of 10a-e. Conversely, the oral absorption rates of 10a-e in rats increased depending on the number of carbon atoms in the alkyl groups; 10d (C3, n-Pr) and 10e (C3, i-Pr) had high oral absorption rates (>90% at 10 mg/kg). These results demonstrated that the introduction of alkyl groups onto C-7 aminoazetidine is useful for the improvement of the oral absorption rates of these drugs while maintaining their antibacterial activities. As a conclusion, from this series of fluoroquinolones, WQ-3810 (10e), having 3-isopropylaminoazetidine as the C-7 substituent, was identified as an orally active antibacterial agent with a potent in vitro activity. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.08.015
• 作为产物：
  描述：

  2,3,5,6-四氟吡啶 、 叔丁胺 在 氯仿 、 水 、 magnesium sulfate 作用下， 以 乙腈 为溶剂， 反应 72.0h， 以to obtain 9.7 g of the title compound as a pale yellow oil的产率得到2-(tert-butylamino)-3,5,6-trifluoropyridine
  参考文献：
  名称：

  Pyridonecarboxylic acid derivatives or their salts, and antibacterial

  摘要：

  提供一种由以下通式（1）表示的吡啶酮羧酸衍生物：##STR1## [其中R.sup.1表示氢原子或羧基保护基；R.sup.2表示羟基，较低的烷氧基或取代或未取代的氨基；R.sup.3表示氢原子或卤素原子；R.sup.4表示氢原子或卤素原子；R.sup.5表示卤素原子或可选取代的饱和环氨基；R.sup.6表示氢原子，卤素原子，硝基或可选保护的氨基；X，Y和Z可以相同也可以不同，分别表示氮原子，-CH.dbd.或-CR.sup.7.dbd.（其中R.sup.7表示较低的烷基，卤素原子或氰基）（但至少有一个X，Y和Z表示氮原子），W表示氮原子或-CR.sup.8.dbd.（其中R.sup.8表示氢原子，卤素原子或较低的烷基）]或其盐，以及包含这种化合物的抗菌剂。

  公开号：

  US06156903A1

文献信息

• Pyridonecarboxylic acid derivatives or their salts and antibacterial
  申请人：Wakunaga Pharmaceuticals Co., Ltd.

  公开号：US05998436A1

  公开（公告）日：1999-12-07

  A pyridonecarboxylic acid derivative represented by the following general formula (1): ##STR1## [wherein R.sup.1 represents hydrogen atom or a carboxyl protective group; R.sup.2 represents hydroxyl group, a lower alkoxy group, or a substituted or unsubstituted amino group; R.sup.3 represents hydrogen atom or a halogen atom; R.sup.4 represents hydrogen atom or a halogen atom; R.sup.5 represents a halogen atom or an optionally substituted saturated cyclic amino group; R.sup.6 represents hydrogen atom, a halogen atom, nitro group, or an optionally protected amino group; X, Y and Z may be the same or different and respectively represent nitrogen atom, --CH.dbd. or --CR.sup.7 .dbd. (wherein R.sup.7 represents a lower alkyl group, a halogen atom, or cyano group) (with the proviso that at least one of X, Y and Z represent the nitrogen atom), and W represents nitrogen atom or --CR.sup.8 .dbd. (wherein R.sup.8 represents hydrogen atom, a halogen atom, or a lower alkyl group)] or its salt, as well as an antibacterial agent containing such compound are provided.

  一种吡啶酮羧酸衍生物，由以下通式（1）表示： ##STR1## [其中R1表示氢原子或羧基保护基团；R2表示羟基、低级烷氧基或取代或未取代的氨基；R3表示氢原子或卤素原子；R4表示氢原子或卤素原子；R5表示卤素原子或可选择性取代的饱和环状氨基；R6表示氢原子、卤素原子、硝基或可选择性保护的氨基；X、Y和Z可以相同或不同，分别表示氮原子、--CH＝或--CR7＝（其中R7表示低级烷基、卤素原子或氰基）（条件是X、Y和Z中至少有一个表示氮原子），W表示氮原子或--CR8＝（其中R8表示氢原子、卤素原子或低级烷基）]或其盐，以及含有此类化合物的抗菌剂。
• Pyridonecarboxylic acid derivatives or their salts, and antibacterial
  申请人：Wakunaga Pharmaceutical Co., Ltd.

  公开号：US06133284A1

  公开（公告）日：2000-10-17

  A pyridonecarboxylic acid derivative represented by the following general formula (1): ##STR1## [wherein R.sup.1 represents hydrogen atom or a carboxyl protective group; R.sup.2 represents hydroxyl group, a lower alkoxy group, or a substituted or unsubstituted amino group; R.sup.3 represents hydrogen atom or a halogen atom; R.sup.4 represents hydrogen atom or a halogen atom; R.sup.5 represents a halogen atom or an optionally substituted saturated cyclic amino group; R.sup.6 represents hydrogen atom, a halogen atom, nitro group, or an optionally protected amino group; X, Y and Z may be the same or different and respectively represent nitrogen atom, --CH.dbd. or --CR.sup.7 .dbd. (wherein R.sup.7 represents a lower alkyl group, a halogen atom, or cyano group) (with the proviso that at least one of X, Y and Z represent the nitrogen atom), and W represents nitrogen atom or --CR.sup.8 .dbd. (wherein R.sup.8 represents hydrogen atom, a halogen atom, or a lower alkyl group)] or its salt, as well as an antibacterial agent containing such compound are provided.

  提供一种由以下通式（1）表示的吡啶酮羧酸衍生物：##STR1## [其中，R.sup.1表示氢原子或羧基保护基；R.sup.2表示羟基、低级烷氧基或取代或未取代的氨基；R.sup.3表示氢原子或卤素原子；R.sup.4表示氢原子或卤素原子；R.sup.5表示卤素原子或可选取代的饱和环氨基基团；R.sup.6表示氢原子、卤素原子、硝基基团或可选保护的氨基基团；X、Y和Z可以相同也可以不同，分别表示氮原子、--CH.dbd.或--CR.sup.7.dbd.（其中，R.sup.7表示低级烷基、卤素原子或氰基）（但至少其中一个为氮原子），W表示氮原子或--CR.sup.8.dbd.（其中，R.sup.8表示氢原子、卤素原子或低级烷基）]或其盐，以及含有此类化合物的抗菌剂。
• Intermediates for use in preparing novel pyridonecarboxylic acid derivatives or their salts
  申请人：WAKUNAGA PHARMACEUTICAL CO., LTD.

  公开号：EP0952151A2

  公开（公告）日：1999-10-27

  An intermediate useful for preparing novel pyridonecarboxylic acid derivatives or their salts, the intermediate represented by the following general formula (C) : wherein X represents a nitrogen atom, Y represents -CH= or -CR7= (wherein R7 represents a lower alkyl group or a halogen atom), Z represents -CH=, R2a represents a substituted or unsubstituted amino group substituted with a protect group and R3 represents a hydrogen atom or a halogen atom.

  一种用于制备新型吡啶羧酸衍生物或其盐类的中间体，该中间体由以下通式（C）代表： 其中 X 代表氮原子，Y 代表 -CH= 或 -CR7=（其中 R7 代表低级烷基或卤素原子），Z 代表 -CH=，R2a 代表被保护基团取代或未被取代的氨基，R3 代表氢原子或卤素原子。
• NOVEL PYRIDONECARBOXYLIC ACID DERIVATIVES OR THEIR SALTS AND ANTIBACTERIAL AGENT COMPRISING THE SAME AS THE ACTIVE INGREDIENT
  申请人：WAKUNAGA PHARMACEUTICAL CO., LTD.

  公开号：EP0911327B1

  公开（公告）日：2001-12-05
• Pyridonecarboxylic acid derivatives as antibacterial agents
  申请人：WAKUNAGA PHARMACEUTICAL CO., LTD.

  公开号：EP0992501B1

  公开（公告）日：2002-08-28