8-alkoxyquinolonecarboxylic acid and salts thereof

• US 4,980,470 A
• Filed: 01/16/1987
• Issued: 12/25/1990
• Est. Priority Date: 01/21/1986
• Status: Expired due to Term

• Current Assignee: Kyorin Pharmaceutical Company Limited (Kyorin Holdings Incorporated)
• Original Assignee: Kyorin Pharmaceutical Company Limited (Kyorin Holdings Incorporated)
• Inventors: Ishizaki, Takayoshi, Hirai, Keiji, Suzue, Seigo, Masuzawa, Kuniyoshi
• Primary Examiner(s): Raymond, Richard L.
• Assistant Examiner(s): TURNIPSEED, JAMES
• Application Number:
  US07/003,822
• Time in Patent Office: 1,439 Days
• Field of Search: 544/363, 546/156
• US Class Current: 544/363
• CPC Class Codes: A61P 31/04 Antibacterial agents
• CPC Class Codes: C07D 215/56 with oxygen atoms in position 4
• CPC Class Codes: C07D 401/04 directly linked by a ring-member-to-ring-member bond

Abstract

Quinolonecarboxylic acid derivatives of the following formula: ##STR1## wherein R indicates a hydrogen atom or lower alkyl group, R¹ indicates a lower alkyl group, R² indicates a hydrogen atom, amino group or nitro group, X indicates a halogen atom, and Z indicates a halogen atom, piperazino group, N-methylpiperazino group, 3-methylpiperazino group, 3-hydroxypyrrolidino group, or pyrrolidino group of the following formula, ##STR2## (here, n is 0 or 1, R³ indicates a hydrogen atom or lower alkyl group, R⁴ indicates a hydrogen atom, lower alkyl group and R⁵ indicates a hydrogen atom, lower alkyl group, acyl group or alkoxycarbonyl group), the hydrates and pharmaceutically acceptable salts thereof are useful as antibacterial agents.

Claims

1. 8-Alkoxyquinolonecarboxylic acid derivatives represented by a general formula (I);

##STR27## wherein R indicates a hydrogen atom or lower alkyl group, R¹ indicates a lower alkyl group, R² indicates a hydrogen atom X indicates a halogen atom, and Z indicates a halogen atom, piperazino group, N-methylpiperazino group, 3-methylpiperazino group, 3-hydroxypyrrolidino group, or pyrrolidino group of the following formula, ##STR28## where, n is 0 or 1, R³ indicates a lower alkylgroup, R⁴ indicates a hydrogen atom, lower alkyl group, hydroxy-substituted lower alkyl group or halogenated lower alkyl group and R⁵ indicates a hydrogen atom, lower alkyl group, acyl group or alkoxycarbonyl group, the hydrates or the pharmaceutically acceptable acid addition or alklai salts thereof.

2. 8-Alkoxyquinolonecarboxylic acid derivative as claimed in claim 1, wherein said derivative is 1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid.

3. 8-Alkoxyquinolonecarboxylic acid derivative as claimed in claim 1, wherein said derivative is 1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid.

4. 8-Alkoxyquinolonecarboxylic acid derivative as claimed in claim 1, wherein said derivative is 1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid.

5. 8-Alkoxyquinolonecarboxylic acid derivative as claimed in claim 1, wherein said derivative is 7-(cis-3-amino-4-methyl-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid.

6. 8-Alkoxyquinolonecarboxylic acid derivative as claimed in claim 1, wherein said derivative is 7-(trans-3-amino-4-methyl-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid.

7. 8-Alkoxyquinolonecarboxylic acid derivative as claimed in claim 1, wherein said derivative is 7-(3-amino-4-methyl-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid.

8. 8-Alkoxyquinolonecarboxylic acid derivative as claimed in claim 1, wherein said derivative is 1-cyclopropyl-6-fluoro-1,4-dihydro-8-ethoxy-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid.