1-ethyl-6-fluoro-1,4-dihydro-7-(3-methylamino-1-pyrrolidinyl)-4-oxo-1,8-naphthyridine-3-carboxylic acid | 79286-81-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 1-ethyl-6-fluoro-1,4-dihydro-7-(3-methylamino-1-pyrrolidinyl)-4-oxo-1,8-naphthyridine-3-carboxylic acid
• 英文别名: 1,8-Naphthyridine-3-carboxylic acid, 1,4-dihydro-1-ethyl-6-fluoro-7-(3-(methylamino)-1-pyrrolidinyl)-4-oxo-；1-ethyl-6-fluoro-7-[3-(methylamino)pyrrolidin-1-yl]-4-oxo-1,8-naphthyridine-3-carboxylic acid
• CAS: 79286-81-0
• 化学式: C₁₆H₁₉FN₄O₃
• 分子量: 334.35
• InChiKey: SDUXFWBQJKQSLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  85.8
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  依诺沙星杂质3 在 sodium hydroxide 、 三乙胺 作用下， 反应 4.0h， 生成 1-ethyl-6-fluoro-1,4-dihydro-7-(3-methylamino-1-pyrrolidinyl)-4-oxo-1,8-naphthyridine-3-carboxylic acid
  参考文献：
  名称：

  吡啶酮羧酸作为抗菌剂。4. 7-（3-氨基-1-吡咯烷基）-1-乙基-6-氟-1,4-二氢-4-氧代-1,8-萘啶-3-羧酸及其类似物的合成及抑菌活性。

  摘要：

  用1-取代的7-氯-，7-（乙基磺酰基）-和7-（甲苯磺酰氧基）-制备在C-7具有氨基和/或羟基取代的环状氨基的标题化合物（28-56）。 6-氟-1,4-二氢-4-氧代-1,8-萘啶-3-羧酸及其乙酯（3-7）与环状胺，例如3-氨基吡咯烷。N-1取代基包括乙基，乙烯基和2-氟乙基。作为体外和体内抗菌筛选的结果，三种化合物，1-乙基和1-乙烯基-7-（3-氨基-1-吡咯烷基）-6-氟-1,4-二氢-4-氧代-发现1,8-萘啶-3-羧酸（33a和33b）和1-乙烯基-7- [3-（甲基氨基）-1-吡咯烷基]类似物34b具有比依诺沙星（2）更高的活性。值得进一步的生物学研究。讨论了构效关系。

  DOI：

  10.1021/jm00378a004

文献信息

• Naphthyridine derivatives
  申请人：Dainippon Pharmaceutical Co., Ltd.

  公开号：US04341784A1

  公开（公告）日：1982-07-27

  The present invention provides a 1,8-naphthyridine compound of the formula ##STR1## wherein R is hydrogen, methyl, ethyl or propyl, and a nontoxic pharmaceutically acceptable salt thereof, and a process for preparing a 1,8-naphthyridine compound of the above formula which comprises (A) reacting a compound of the formula ##STR2## wherein Y is halogen, lower alkoxy, lower alkylthio, lower alkylsulfinyl, lower alkylsulfonyl, lower alkylsulfonyloxy or arylsulfonyloxy, and R.sub.1 is hydrogen or lower alkyl, with a compound of the formula ##STR3## wherein R.sub.2 is hydrogen or a protective group for the amino group, and R is as defined above, and when a reaction product in which R.sub.1 is lower alkyl and/or R.sub.2 is the amino protective group is obtained, treating it with an acid or base, and/or reductively cleaving it, (B) decomposing a compound of the formula ##STR4## wherein A .crclbar. is a fluorine-containing anion, and R.sub.1 and R.sub.2 are as defined above, and when a reaction product in which R.sub.1 is lower alkyl and/or R.sub.2 is the amino protective group is obtained, treating it with an acid or base, and/or reductively cleaving it, (C) treating a compound of the formula ##STR5## wherein R'.sub.1 is hydrogen or lower alkyl, R'.sub.2 is hydrogen or a protective group for the amino group, provided that R'.sub.1 and R'.sub.2 are not hydrogen atoms at the same time, and R is as defined above, with an acid or base, and/or reductively cleaving it, and optionally converting the resulting compound to a nontoxic pharmaceutically acceptable salt thereof. The 1,8-naphthyridine compound is useful as an antibacterial agent.

  本发明提供了一种1,8-萘啶化合物，其化学式为##STR1##其中R为氢、甲基、乙基或丙基，以及其非毒性药用可接受的盐，并且提供了一种制备上述化合物的1,8-萘啶化合物的方法，包括(A)将化学式为##STR2##其中Y为卤素、较低烷氧基、较低烷基硫基、较低烷基磺酰基、较低烷基磺酰氧基或芳基磺酰氧基的化合物，R.sub.1为氢或较低烷基，与化学式为##STR3##其中R.sub.2为氢或氨基的保护基，R如上所定义，进行反应，当得到R.sub.1为较低烷基和/或R.sub.2为氨基保护基的反应产物时，用酸或碱处理，和/或还原性裂解它，(B)分解化学式为##STR4##其中A .crclbar.为含氟阴离子，R.sub.1和R.sub.2如上所定义，当得到R.sub.1为较低烷基和/或R.sub.2为氨基保护基的反应产物时，用酸或碱处理，和/或还原性裂解它，(C)用酸或碱处理化学式为##STR5##其中R'.sub.1为氢或较低烷基，R'.sub.2为氢或氨基的保护基，前提是R'.sub.1和R'.sub.2不能同时为氢原子，R如上所定义，并可选择将得到的化合物转化为其非毒性药用可接受的盐。1,8-萘啶化合物可用作抗菌剂。
• Naphthyridine derivatives, processes for their preparation and pharmaceutical compositions containing them
  申请人：Société anonyme dite: LABORATOIRE ROGER BELLON

  公开号：EP0027752A1

  公开（公告）日：1981-04-29

  The present invention provides a 1,8-naphthyridine compound of the formula wherein R is hydrogen, methyl, ethyl or propyl, and a nontoxic pharmaceutically acceptable salt thereof, -an antibacterial agent comprising said 1,8-naphtyridine compound -and a process for prearing a 1,8-naphtyridine compound of the above formula which comprises (A) reacting a compound oftheformula: with a compound of the formula or (B) decomposing a compound of the formula or (C) treating a compound of the formula with an acid or base, and/or reducrively cleaving it.

  本发明提供了一种式中 R 为氢、甲基、乙基或丙基的 1，8-萘啶化合物及其无毒的药学上可接受的盐，一种包含上述 1，8-萘啶化合物的抗菌剂，以及一种预制上述式中 1，8-萘啶化合物的工艺，该工艺包括（A）使式中化合物：与式中化合物反应，或（B）分解式中化合物，或（C）用酸或碱处理式中化合物，和/或还原裂解式中化合物。
• MATSUMOTO, DZYUNITI;TAKASEH, JOSIYUKI;NISIMURA, JOSIRO
  作者：MATSUMOTO, DZYUNITI、TAKASEH, JOSIYUKI、NISIMURA, JOSIRO

  DOI：——

  日期：——
• EGAWA, HIROSHI;MIYAMOTO, TERUYUKI;MINAMIDA, AKIRA;NISHIMURA, YOSHIRO;OKAD+, J. MED. CHEM., 1984, 27, N 12, 1543-1548
  作者：EGAWA, HIROSHI、MIYAMOTO, TERUYUKI、MINAMIDA, AKIRA、NISHIMURA, YOSHIRO、OKAD+

  DOI：——

  日期：——
• JPS5770889A
  申请人：——

  公开号：JPS5770889A

  公开（公告）日：1982-05-01