Quinolinecarboxylic acid derivatives, antibacterial agent containing the same

• US 5,166,203 A
• Filed: 05/12/1991
• Issued: 11/24/1992
• Est. Priority Date: 08/30/1990
• Status: Expired due to Fees

• Current Assignee: Kanebo, Ltd. (HOYU Company Limited)
• Original Assignee: Kanebo, Ltd. (HOYU Company Limited)
• Inventors: Kondo, Hirosata, Inoue, Yoshimasa, Taguchi, Masahiro, Sakamoto, Fumio, Kotera, Yasuo, Jinbo, Yoshikazu
• Primary Examiner(s): Ford, John M.
• Application Number:
  US07/703,739
• Time in Patent Office: 562 Days
• Field of Search: 544/105, 544/115, 544/343, 514/250, 514/230.5, 514/233.2
• US Class Current: 514/230.5
• CPC Class Codes: C07D 513/16 Peri-condensed systems
• CPC Class Codes: C07D 519/00 Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00

Abstract

Novel quinolinecarboxylic acid derivatives of the formula: ##STR1## wherein Z is ##STR2## or ##STR3## in which R¹ is hydrogen atom, a halogen atom, hydroxy or a lower alkyloxy; R² is a halogen atom, hydroxy or a lower alkyloxy; R³ is a lower alkyl; and R⁴ is hydroxy or a di(lower alkyl)amino, and a pharmaceutically acceptable salt thereof, which have excellent antibacterial activities and are useful as an antibacterial agent, a pharmaceutical composition containing the same, and process for preparing the same.

Claims

1. A quinolinecarboxylic acid derivative of the formula:

##STR25## wherein ##STR26## in which R¹ is hydrogen, chlorine, fluorine hydroxy, methoxy or ethoxy, or a pharmaceutically acceptable salt thereof.

2. The compound according to claim 1, wherein Z is ##STR27## (where R¹ is hydrogen, chlorine, fluorine, hydroxy, methoxy or ethoxy, or a pharmaceutically acceptable salt thereof.

3. The compound according to claim 1, wherein Z is ##STR28## or a pharmaceutically acceptable salt thereof.

4. The compound according to claim 1, which is a member selected from the following compounds:

9,1-(Methylimino)methano-7-fluoro-8-(2-methylmorpholino)-5-oxo-5H-thiazolo[3,2-a]quinoline-4-carboxylic acid, or a pharmaceutically acceptable salt thereof;

9,1-(Methylimino)methano-7-fluoro-8-(2-hydroxymethylmorpholino)-5-oxo-5H-thiazolo[3,2-a]quinoline-4-carboxylic acid, or a pharmaceutically acceptable salt thereof;

9,1-(Methylimino)methano-7-fluoro-8-(2-fluoromethylmorpholino)-5-oxo-5H-thiazolo[3,2-a]quinoline-4-carboxylic acid, or a pharmaceutically acceptable salt thereof;

9,1-(Methylimino)methano-7-fluoro-8-(2-chloromethylmorpholino)-5-oxo-5H-thiazolo[3,2-a]quinoline-4-carboxylic acid, or a pharmaceutically acceptable salt thereof;

9,1-(Methylimino)methano-7-fluoro-8-(2-methoxymethylmorpholino)-5-oxo-5H-thiazolo[3,2-a]quinoline-4-carboxylic acid, or a pharmaceutically acceptable salt thereof;

9,1-(Methylimino)methano-7-fluoro-8-[(6R)-1,8-diaza-4-oxabicyclo[4.4.0]deca-8-yl]-5-oxo-5H-thiazolo[3,2-a]quinoline-4-carboxylic acid, or a pharmaceutically acceptable salt thereof;

8. A method for providing an antibacterial effect to a subject need thereof, comprising administering to the subject an antibacterially-effective amount of a compound according to claim 1 or a pharmaceutically acceptable salt thereof.

5. 1-(Methylimino)methano-7-fluoro-8-[(2S)-2-hydroxymethylmorpholino]-5-oxo-5H-thiazolo[3,2-a]quinoline-4-carboxylic acid, or a pharmaceutically acceptable salt thereof;

9,1-(Methylimino)methano-7-fluoro-8-[(2R)-2-hydroxymethylmorpholino]-5-oxo-5H-thiazolo[3,2-a]quinoline-4-carboxylic acid, or a pharmaceutically acceptable salt thereof;

9,1-(Methylimino)methano-7-fluoro-8-[(2S)-2-methoxymethylmorpholino]-5-oxo-5H-thiazolo[3,2-a]quinoline-4-carboxylic acid, or a pharmaceutically acceptable salt thereof;

9,1-(Methylimino)methano-7-fluoro-8-[(2R)-2-methoxymethylmorpholino]-5-oxo-5H-thiazolo[3,2-a]quinoline-4-carboxylic acid, or a pharmaceutically acceptable salt thereof;

9,1-(Methylimino)methano-7-fluoro-8-(2-ethoxymethylmorpholino)-5-oxo-5H-thiazolo[3,2-a]quinoline-4-carboxylic acid, or a pharmaceutically acceptable salt thereof.

7. The composition of claim 5, which is in a form for oral administration.

9. The method of claim 7, wherein the compound is administered orally.

6. An antibacterial composition comprising as an active ingredient an effective amount of a quinolinecarboxylic acid derivative of the formula:

##STR29## wherein ##STR30## in which R¹ is hydrogen, chlorine, fluorine, hydroxy, methoxy or ethoxy, or a pharmaceutically acceptable salt thereof, in admixture with pharmaceutically acceptable carrier or diluent.