8-chloro-1-cyclopropyl-6-fluoro-5-methyl-7-(1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid | 119914-74-8

• 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-chloro-1-cyclopropyl-6-fluoro-5-methyl-7-(1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
• 英文别名: 8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-5-methyl-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid；8-chloro-1-cyclopropyl-6-fluoro-5-methyl-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid
• CAS: 119914-74-8
• 化学式: C₁₈H₁₉ClFN₃O₃
• 分子量: 379.819
• InChiKey: FTCDLPYLHNMBFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  72.9
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-5-methyl-4-oxo-3-quinolinecarboxylic acid 生成 8-chloro-1-cyclopropyl-6-fluoro-5-methyl-7-(1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
  参考文献：
  名称：

  DOMAGALA, JOHN M.;HAGEN, SUSAN E.;KIELY, JOHN S.

  摘要：

  DOI：

文献信息

• Antibacterial agents
  申请人：Warner-Lambert Company

  公开号：US04920120A1

  公开（公告）日：1990-04-24

  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.

  描述了新型萘啶基和喹啉基羧酸作为抗菌剂的小说，以及它们的制造、配方和用于治疗细菌感染的方法，包括用于制造抗菌剂的某些新型中间体的描述。
• Novel quinoline derivatives, processes for preparation thereof and antibacterial agent containing them
  申请人：Dainippon Pharmaceutical Co., Ltd.

  公开号：EP0319906A2

  公开（公告）日：1989-06-14

  1-Substituted-6-fluoro-5-methyl-7-(piperazinyl or pyrrolidinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acids (I) and processes for preparation thereof. The acids are used for treatment of a bacterial infectious desease.

  1-取代-6-氟-5-甲基-7-(哌嗪基或吡咯烷基)-1,4-二氢-4-氧代喹啉-3-羧酸 (I) 及其制备方法。这些酸可用于治疗细菌性传染病。
• Benzoheterocyclic compounds
  申请人：OTSUKA PHARMACEUTICAL CO., LTD.

  公开号：EP0565132A2

  公开（公告）日：1993-10-13

  Novel 4-oxoquinoline-3-carboxylic acid compounds of the formula: wherein R¹ is cyclopropyl which may have 1 to 3 substituents of alkyl and halogen; phenyl which may be substituted by 1 to 3 substituents of alkoxy, halogen and OH; alkyl which may be substituted by halogen, alkanoyloxy or OH; alkenyl; or thienyl, R² is 5- to 9-membered saturated or unsaturated heterocyclic ring which may be sustituted, R³ is H, alkyl or halogen, R⁴ is alkyl or halogen, R is H or alkyl, R¹ and R³ may be taken together to form wherein R³¹ is H or alkyl, and X is halogen, provided that R³ and R⁴ are not simultaneously halogen, and that when R³ is H, R⁴ is alkyl, and salts thereof, said compounds having excellent antimicrobial activity and hence being useful as an antimicrobial agent, and a pharmaceutical composition containing said compound as an active ingredient.

  式中的新型 4-氧代喹啉-3-羧酸化合物： 其中 R¹ 是环丙基，可被 1 至 3 个烷基和卤素取代；苯基，可被 1 至 3 个烷氧基、卤素和 OH 取代；烷基，可被卤素、烷酰氧基或 OH 取代；烯基；或噻吩基，R² 是 5 至 9 元饱和或不饱和杂环，可被取代，R³ 是 H、烷基或卤素，R⁴ 是烷基或卤素，R 是 H 或烷基，R¹ 和 R³ 可结合在一起形成 其中 R³¹ 是 H 或烷基，X 是卤素，条件是 R³ 和 R⁴ 不同时是卤素，当 R³ 是 H 时，R⁴ 是烷基，以及它们的盐，所述化合物具有优异的抗菌活性，因此可用作抗菌剂，以及含有所述化合物作为活性成分的药物组合物。
• [EN] HETEROCYCLO-SUBSTITUTED IMIDAZOLES FOR THE TREATMENT OF INFLAMMATION<br/>[FR] IMIDAZOLES A SUBSTITUTION HETEROCYCLO UTILISES POUR TRAITER L'INFLAMMATION
  申请人：G.D. SEARLE & CO.

  公开号：WO1997027181A1

  公开（公告）日：1997-07-31

  (EN) A class of imidazolyl compounds is described for use in treating inflammation. Compounds of particular interest are defined by formula (V), wherein R3 is a radical selected from hydrido, alkyl, haloalkyl, aralkyl, heterocycloalkyl, heteroaralkyl, acyl, cyano, alkoxy, alkylthio, alkylthioalkyl, alkylsulfonyl, cycloalkylthio, cycloalkylthioalkyl, cycloalkylsulfonyl, cycloalkylsulfonylalkyl, haloalkylsulfonyl, arylsulfonyl, halo, hydroxyalkyl, alkoxyalkyl, alkylcarbonyl, arylcarbonyl, aralkylcarbonyl, heterocyclocarbonyl, cyanoalkyl, aminoalkyl, alkylaminoalkyl, N-arylaminoalkyl, N-alkyl-N-arylaminoalkyl, carboxyalkyl, alkoxycarbonylalkyl, alkoxycarbonyl, haloalkylcarbonyl, carboxyl, aminocarbonyl, alkylaminocarbonyl, alkylaminocarbonylalkyl, heteroarylalkoxyalkyl, heteroaryloxyalkyl, heteroarylthioalkyl, aralkoxy, aralkylthio, heteroaralkoxy, heteroaralkylthio, heteroarylalkylthioalkyl, heteroaryloxy, heteroarylthio, arylthioalkyl, aryloxyalkyl, arylthio, aryloxy, aralkylthioalkyl, aralkoxyalkyl, aryl and heteroaryl; wherein R4 is a radical selected from hydrido, alkyl and halo; and wherein R13 and R14 are independently selected from aryl and heterocyclo, wherein R13 and R14 are optionally substituted at a substitutable position with one or more radicals independently selected from alkylsulfonyl, aminosulfonyl, halo, alkylthio, alkyl, cyano, carboxyl, alkoxycarbonyl, haloalkyl, hydroxyl, alkoxy, hydroxyalkyl, alkoxyalkyl, haloalkoxy, amino, alkylamino, arylamino and nitro; provided at least one of R13 and R14 is aryl substituted with alkylsulfonyl or aminosulfonyl; or a pharmaceutically-acceptable salt thereof.(FR) Cette invention concerne une classe de composés d'imidazolyle destinés à être utilisés pour traiter l'inflammation. Des composés particulièrement intéressants sont définis par la formule générale (V). Dans la formule R3 représente un radical sélectionné entre hybrido, alkyle, haloalkyle, aralkyle, hétérocycloalkyle, hétéroaralkyle, acyl, cyano, alkoxy, alkylthio, alkylthioalkyle, alkylsulfonyle, cycloalkylthio, cycloalkylthioalkyle, cycloalkylsulfonyle, cycloalkylsulfonylalkyle, haloalkylsulfonyle, arylsulfonyle, halo, hydroxyalkyle, alcoxyalkyle, alkylcarbonyle, arylcarbonyle, aralkylcarbonyle, hétérocyclocarbonyle, cyanoalkyle, aminoalkyle, alkylaminoalkyle, N-arylaminoalkyle, N-alkyl-N-arylaminoalkyle, carboxyalkyle, alkoxycarbonylalkyle, alkoxycarbonyle, haloalkylcarbonyle, carboxyle, aminocarbonyle, alkylaminocarbonyle, alkylaminocarbonylalkyle, hétéroarylalkoxyalkyle, hétéroaryloxyalkyle, hétéroarylthioalkyle, aralcoxy, aralkylthio, hétéroaralcoxy, hétéroaralkylthio, hétéroarylalkylthioalkyle, hétéroaryloxy, hétéroarylthio, arylthioalkyle, aryloxyalkyle, arylthio, aryloxy, aralkylthioalkyle, aralcoxyalkyle, aryle et hétéroaryle; R4 représente un radical sélectionné entre hybrido, alkyle et halo; R13 and R14 sont indépendamment sélectionnées entre aryle et hétérocyclo, R13 et R14 sont facultativement substitués à une position substituable à un ou plusieurs radicaux sélectionnés indépendamment entre alkylsulfonyle, aminosulfonyle, halo, alkylthio, alkyle, cyano, carboxyle, alkoxycarbonyle, haloalkyle, hydroxyle, alcoxy, hydroxyalkyle, alcoxyalkyle, haloalcoxy, amino, alkylamino, arylamino et nitro; à condition qu'au moins un des éléments R13 et R14 représente aryle remplacé par alkylsulfonyle ou aminosulfonyle ou bien un sel pharmaceutiquement acceptable de ces derniers.

  描述了一类咪唑基化合物，用于治疗炎症。特别感兴趣的化合物由通式(V)定义，其中R3为选自氢代、烷基、卤代烷基、芳烷基、杂环烷基、杂芳烷基、酰基、氰基、烷氧基、烷硫基、烷硫基烷基、烷基磺酰基、环烷基硫基、环烷基硫基烷基、环烷基磺酰基、环烷基磺酰基烷基、卤代烷基磺酰基、芳基磺酰基、卤素、羟基烷基、烷氧基烷基、烷基羰基、芳基羰基、芳烷基羰基、杂环羰基、氰基烷基、氨基烷基、烷基氨基烷基、N-芳基氨基烷基、N-烷基-N-芳基氨基烷基、羧基烷基、烷氧羰基烷基、烷氧羰基、卤代烷基羰基、羧基、氨基羰基、烷基氨基羰基、烷基氨基羰基烷基、杂芳基烷氧基烷基、杂芳基氧基烷基、杂芳基硫基烷基、芳烷氧基、芳烷基硫基、杂芳烷氧基、杂芳烷基硫基、杂芳基烷基硫基烷基、杂芳基氧基、杂芳基硫基、芳基硫基烷基、芳基氧基烷基、芳基硫基、芳基氧基、芳烷基硫基烷基、芳烷氧基烷基、芳基和杂芳基；其中R4为选自氢代、烷基和卤素的基团；并且R13和R14独立地选自芳基和杂环基，其中R13和R14可在一个可被取代的位置上被一个或多个基团取代，这些基团独立地选自烷基磺酰基、氨基磺酰基、卤素、烷硫基、烷基、氰基、羧基、烷氧羰基、卤代烷基、羟基、烷氧基、羟基烷基、烷氧基烷基、卤代烷氧基、氨基、烷基氨基、芳基氨基和硝基；前提是至少一个R13或R14为被烷基磺酰基或氨基磺酰基取代的芳基；或者其药学上可接受的盐。
• Synthesis and biological activity of 5-alkyl-1,7,8-trisubstituted-6-fluoroquinoline-3-carboxylic acids
  作者：Susan E. Hagen、John M. Domagala、Carl L. Heifetz、Judith Johnson

  DOI：10.1021/jm00107a040

  日期：1991.3

  A series of 5-alkyl-1,7,8-trisubstituted-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids was prepared and evaluated for in vitro and in vivo antibacterial activity. When compared to the 5-hydrogen analogues, the presence of the 5-methyl group enhanced in vitro potency for those compounds containing a cyclopropyl moiety at N1 but decreased potency for those containing an ethyl group at N1. Replacing the 5-methyl with a 5-ethyl significantly reduced the efficacy. In general, the 5-methyl and 5-hydrogen analogues were equipotent in vivo. Several of the 5-methyl-1-cyclopropylquinolones displayed excellent in vitro and in vivo activity, warranting further development.