2,6-Dichloro-5-fluoro-4-methyl-nicotinoyl chloride | 149366-73-4

• 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: 2,6-Dichloro-5-fluoro-4-methyl-nicotinoyl chloride
• 英文别名: 2,6-Dichloro-5-fluoro-4-methylnicotinoyl chloride；2,6-dichloro-5-fluoro-4-methylpyridine-3-carbonyl chloride
• CAS: 149366-73-4
• 化学式: C₇H₃Cl₃FNO
• 分子量: 242.464
• InChiKey: WTNRFVCOYIPYKD-UHFFFAOYSA-N

物化性质

• 沸点：
  301.6±37.0 °C(Predicted)
• 密度：
  1.580±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,6-Dichloro-5-fluoro-4-methyl-nicotinoyl chloride 在 sodium hydroxide 、 乙酸酐 、 sodium hydride 、 对甲苯磺酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 1,4-二氧六环 、 乙醇 、 乙腈 为溶剂， 反应 23.5h， 生成 7-((3S)-3-amino-1-pyrrolidinyl)-1,4,-dihydro-1-(2,4-difluorophenyl)-6-fluoro-5-methyl-4-oxo-1,8-napthyridine-3-carboxylic acid
  参考文献：
  名称：

  Fluoronaphthyridines as antibacterial agents. 4. Synthesis and structure-activity relationships of 5-substituted 6-fluoro-7-(cycloalkylamino)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids

  摘要：

  A series of 5-substituted-6-fluoro-7-(cycloalkylamino)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids have been prepared and tested for their in vitro and in vivo antibacterial activities. The 5-methyl group gave better in vitro activity with the 1-cyclopropyl appendage, but poorer activity with the 1-tert-butyl moiety. With the 1-(2,4-difluorophenyl) substitution, the influence of the 7-cycloalkylamino group was determinant: a (3S)-3-amino-pyrrolidine was shown to enhance greatly the in vitro and in vivo activity of the 5-methyl derivative. Compound 33 (BMY 43748) was selected as a promising candidate for an improved therapeutic agent.

  DOI：

  10.1021/jm00081a013
• 作为产物：
  描述：

  2,6-二氯-5-氟-4-甲基吡啶-3-羧酸 在 五氯化磷 作用下， 反应 0.13h， 生成 2,6-Dichloro-5-fluoro-4-methyl-nicotinoyl chloride
  参考文献：
  名称：

  Fluoronaphthyridines as antibacterial agents. 4. Synthesis and structure-activity relationships of 5-substituted 6-fluoro-7-(cycloalkylamino)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids

  摘要：

  A series of 5-substituted-6-fluoro-7-(cycloalkylamino)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids have been prepared and tested for their in vitro and in vivo antibacterial activities. The 5-methyl group gave better in vitro activity with the 1-cyclopropyl appendage, but poorer activity with the 1-tert-butyl moiety. With the 1-(2,4-difluorophenyl) substitution, the influence of the 7-cycloalkylamino group was determinant: a (3S)-3-amino-pyrrolidine was shown to enhance greatly the in vitro and in vivo activity of the 5-methyl derivative. Compound 33 (BMY 43748) was selected as a promising candidate for an improved therapeutic agent.

  DOI：

  10.1021/jm00081a013

文献信息

• Antibacterial agents
  申请人：Otsuka Pharmaceutical Co., Ltd.

  公开号：US05585491A1

  公开（公告）日：1996-12-17

  Novel naphthyridine-, and quinolinecarboxylic acids as antibacterial agents are described as well as methods for their manufacture, formulation, and use in treating bacterial infections including the description of certain novel intermediates used in the manufacture of the antibacterial agents.

  本文描述了新型萘啶和喹啉羧酸作为抗菌剂的特点，以及制造、配方和用于治疗细菌感染的方法，并描述了在制造抗菌剂过程中使用的某些新型中间体。
• Naphthyridone carboxylic acid derivatives and antibacterial compositions containing them
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0544981A2

  公开（公告）日：1993-06-09

  The application comprises new compounds of the formula IV wherein R₂ is cyclopropyl or 2,4-difluorophenyl and Z is a group wherein R₅ and R₆ are each independently hydrogen and alkyl with 1 to 4 carbon atoms and n is an integer of from 0 to 4, a process of manufacture and pharmaceutical compositions useful as antibacterials.

  本申请包括式 IV 的新化合物 其中 R₂ 是环丙基或 2,4-二氟苯基，Z 是一个基团 其中R₅和R₆各自独立地为氢和含有1至4个碳原子的烷基，n为0至4的整数，该化合物的制造工艺和用作抗菌剂的药物组合物。
• US5585491A
  申请人：——

  公开号：US5585491A

  公开（公告）日：1996-12-17