US4499091A
Expired / Lapsed
US
⏱️ 0.0 years remaining
1-Amino (or substituted amino)-1,4-dihydro-4-oxo-6-fluoro-7-heterylquinoline-3-carboxylic acids and their use as antibacterial agents
Assignee: Sanofi SA
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Filing: 1983-02-14
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Granted: 1985-02-12
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Expires: 2003-02-14
Abstract
Abstract Novel 1-R-1,4-dihydro-4-oxo-6-fluoro-7-(Z=N-)-quinolinecarboxylic acids and esters thereof, where R is amino, lower-alkylamino, 2-propenylamino or di-lower-alkylamino, R'' is hydrogen or lower-alkyl, and Z=N is a heterocyclic group, useful as antibacterial agents, are prepared by reacting the corresponding 7-chloroquinoline derivatives with the appropriate heterocyclic compound, Z=NH. A preferred group of compounds are those where Z=N is 1-piperazinyl or 4-lower-alkyl-1-piperazinyl.
Inventors
- 👤 Mark P. Wentland
- 👤 Denis M. Bailey
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 11:47
CPC Classifications
C; C07; C07D; C07D401/00; C07D401/02; C07D401/04; C07D215/00; C07D215/58; C07D413/00; C07D413/02; C07D413/04; C07D417/00; C07D417/02; C07D417/04
Claims Analysis
Total Claims: 35
Claim 1
Independent Claim
82 words
A compound of the formula ##STR11## wherein R is amino, lower-alkylylamino, 2-propenylamino, N-formyl-lower-alkylamino or di-lower-alkylamino; R' is hydrogen or lower-alkyl; and Z═N-- is a heterocyclic group selected from the group consisting of: ##STR12## where n is 2-3, and R" is hydrogen, lower-alkyl or acetyl; ##STR13## where X is O or S; ##STR14## where n' is 1-3; and ##STR15## where m is 1-2; a pharmaceutically acceptable acid-addition salt thereof; or an alkali metal or amine salt of a compound where R' is hydrogen.
Claim 2
Dependent Claim
82 words
A compound of the formula ##STR11## wherein R is amino, lower-alkylylamino, 2-propenylamino, N-formyl-lower-alkylamino or di-lower-alkylamino; R' is hydrogen or lower-alkyl; and Z═N-- is a heterocyclic group selected from the group consisting of: ##STR12## where n is 2-3, and R" is hydrogen, lower-alkyl or acetyl; ##STR13## where X is O or S; ##STR14## where n' is 1-3; and ##STR15## where m is 1-2; a pharmaceutically acceptable acid-addition salt thereof; or an alkali metal or amine salt of a compound where R' is hydrogen.
Claim 3
Dependent Claim
47 words
A compound according to claim 1 of the formula ##STR16## wherein R is amino, lower-alkylamino, 2-propenylamino, N-formyl-lower-alkylamino or di-lower-alkylamino; and R' and R" are hydrogen or lower-alkyl; a pharmaceutically acceptable acid-addition salt thereof; or an alkali metal or amine salt of a compound where R' is hydrogen.
Claim 4
Dependent Claim
14 words
A compound according to claim 2 wherein R is lower-alkylamino and R' is hydrogen.
Claim 5
Dependent Claim
12 words
6-Fluoro-1,4-dihydro-1-methylamino-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid or a pharmaceutically acceptable salt thereof, according to claim 3.
Claim 6
Dependent Claim
6 words
1-Amino-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid, according to claim 2.
Claim 7
Dependent Claim
6 words
1-Amino-6-fluoro-1,4-dihydro-4-oxo-7-(4-methyl-1-piperazinyl)-3-quinolinecarboxylic acid, according to claim 2.
Claim 8
Dependent Claim
6 words
6-Fluoro-1,4-dihydro-1-methylamino-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid, according to claim 3.
Claim 9
Dependent Claim
6 words
1-Ethylamino-6-fluoro-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid, according to claim 3.
Claim 10
Dependent Claim
6 words
6-Fluoro-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo-1-propylamino-3-quinolinecarboxylic acid, according to claim 3.
Claim 11
Dependent Claim
6 words
6-Fluoro-1-dimethylamino-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid, according to claim 2.
Claim 12
Dependent Claim
6 words
7-(4-Ethyl-1-piperazinyl)-6-fluoro-1,4-dihydro-1-methylamino-4-oxo-3-quinolinecarboxylic acid, according to claim 3.
Claim 13
Dependent Claim
6 words
6-Fluoro-1,4-dihydro-1-methylamino-7-[4-(1-methylethyl)-1-piperazinyl]-4-oxo-3-quinolinecarboxylic acid, according to claim 3.
Claim 14
Dependent Claim
6 words
6-Fluoro-1,4-dihydro-1-methylamino-4-oxo-7-(4-propyl-1-piperazinyl)-3-quinolinecarboxylic acid, according to claim 3.
Claim 15
Dependent Claim
6 words
6-Fluoro-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo-1-(2-propenylamino)-3-quinolinecarboxylic acid, according to claim 2.
Claim 16
Dependent Claim
6 words
6-Fluoro-1,4-dihydro-1-methylamino-7-(4-morpholinyl)-4-oxo-3-quinolinecarboxylic acid, according to claim 1.
Claim 17
Dependent Claim
6 words
7-(4-Acetyl-1-piperazinyl)-6-fluoro-1,4-dihydro-1-methylamino-4-oxo-3-quinolinecarboxylic acid, according to claim 1.
Claim 18
Dependent Claim
6 words
6-Fluoro-1,4-dihydro-1-methylamino-4-oxo-7-(1-piperidinyl)-3-quinolinecarboxylic acid, according to claim 1.
Claim 19
Dependent Claim
6 words
6-Fluoro-1,4-dihydro-1-methylamino-4-oxo-7-(1-pyrrolidinyl)-3-quinolinecarboxylic acid, according to claim 1.
Claim 20
Dependent Claim
6 words
6-Fluoro-1,4-dihydro-7-(4-hydroxy-1-piperidinyl)-1-methylamino-4-oxo-3-quinolinecarboxylic acid, according to claim 1.
Claim 21
Dependent Claim
6 words
6-Fluoro-1,4-dihydro-7-(3-hydroxy-1-piperidinyl)-1-methylamino-4-oxo-3-quinolinecarboxylic acid, according to claim 1.
Claim 22
Dependent Claim
6 words
6-Fluoro-7-(hexahydro-1H-1,4-diazapin-1-yl)-1,4-dihydro-1-methylamino-4-oxo-3-quinolinecarboxylic acid, according to claim 1.
Claim 23
Dependent Claim
6 words
6-Fluoro-7-(hexahydro-4-methyl-1H-1,4-diazapin-1-yl)-1,4-dihydro-1-methylamino-4-oxo-3-quinolinecarboxylic acid, according to claim 1.
Claim 24
Dependent Claim
6 words
6-Fluoro-1,4-dihydro-1-methylamino-4-oxo-7-(4-thiomorpholinyl)-3-quinolinecarboxylic acid, according to claim 1.
Claim 25
Dependent Claim
6 words
6-Fluoro-1,4-dihydro-7-(3-hydroxy-1-pyrrolidinyl)-1-methylamino-4-oxo-3-quinolinecarboxylic acid, according to claim 1.
Claim 26
Dependent Claim
6 words
6-Fluoro-1-(N-formylmethylamino)-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid, according to claim 2.
Claim 27
Dependent Claim
23 words
A compound having the formula ##STR17## wherein R' is hydrogen or lower-alkyl, and R° is amino, lower-alkylamino, 2-propenylamino, di-lower-alkylamino, N-formylamino, N-formyl-lower-alkylamino or N-formyl-2-propenylamino.
Claim 28
Dependent Claim
23 words
A compound having the formula ##STR17## wherein R' is hydrogen or lower-alkyl, and R° is amino, lower-alkylamino, 2-propenylamino, di-lower-alkylamino, N-formylamino, N-formyl-lower-alkylamino or N-formyl-2-propenylamino.
Claim 29
Dependent Claim
10 words
A compound according to claim 26 wherein R° is amino.
Claim 30
Dependent Claim
14 words
A compound according to claim 26 wherein R° is lower-alkylamino and R' is hydrogen.
Claim 31
Dependent Claim
6 words
7-Chloro-6-fluoro-1,4-dihydro-1-methylamino-4-oxo-3-quinolinecarboxylic acid, according to claim 28.
Claim 32
Dependent Claim
26 words
A composition for combatting bacteria, which comprises an antibacterially effective amount of a compound according to claim 1 together with one or more pharmaceutically acceptable excipients.
Claim 33
Dependent Claim
20 words
A composition according to claim 30 wherein the antibacterially active compound is 6-fluoro-1,4-dihydro-1-methylamino-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid or a pharmaceutically acceptable salt thereof.
Claim 34
Dependent Claim
20 words
A method for combatting bacteria, which comprises contacting the locus of said bacteria with a composition according to claim 30.
Claim 35
Dependent Claim
20 words
A method according to claim 32 wherein the antibacterially active compound is 6-fluoro-1,4-dihydro-1-methylamino-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid or a pharmaceutically acceptable salt thereof.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-02-12 | 1988-08-13 | 1989-02-12 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-02-12 | 1992-08-13 | 1993-02-12 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-02-12 | 1996-08-13 | 1997-02-12 | $7700.00 | Window Closed / Lapsed |