US4720495A
Expired / Lapsed
US
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Benzo[ij]quinolizine-2-carboxylic acids useful for treating bacterial infection
Assignee: Tanabe Pharma Corp
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Filing: 1986-05-20
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Granted: 1988-01-19
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Expires: 2006-05-20
Abstract
Abstract Benzo[ij]quinolizine-2-carboxylic acid derivatives of the general formula [I] and the salts, and their hydrates are provided: <IMAGE> [I] wherein A is a methylene group and B is a carbonyl group when A and B are linked by a single bond, or A and B unite together to form a vinylene group when A and B are linked by a double bond, R1 is a hydrogen atom, a C1-3 alkyl group or a 2-hydroxyethyl group, R2 and R3 are hydrogen atoms, methyl groups or ethyl groups and may be identical to or different from each other, R3 may be attached to the same carbon atom as R2, R4 is a methyl or ethyl group, and X is a halogen atom. The benzo[ij]quinolizine-2-carboxylic acid derivatives and the salts, and their hydrates have good adsorbability from the digestive tract into the circulating blood and exhibit excellent and long-lasting antibacterial activity.
Inventors
- 👤 Atsushi Takagi
- 👤 Masao Yajima
- 👤 Toshiaki Kikuchi
- 👤 Masaki Saeki
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 20:14
CPC Classifications
C; C07; C07D; C07D455/00; C07D455/03; C07D455/04
Claims Analysis
Total Claims: 30
Claim 1
Independent Claim
136 words
A benzo[ij]quinolizine-2-carboxylic acid of the following formula: ##STR22## Wherein A is a methylene group and B is a carbonyl group when A and B are linked by a single bond, or A and B unite together to form a vinylene group when A and B are linked by a double bond, R 1 is a hydrogen atom, an alkyl group of 1 to 3 carbon atoms or a 2-hydroxyethyl group, R 2 and R 3 are hydrogen atoms, methyl groups or ethyl groups and may be identical to or different from each other, R 3 may be attached to the same carbon atom as R 2 , R 4 is a methyl or ethyl group, and X is a halogen atom; or a physiologically acceptable salt thereof, or a hydrate of the compound or the salt.
Claim 2
Dependent Claim
136 words
A benzo[ij]quinolizine-2-carboxylic acid of the following formula: ##STR22## Wherein A is a methylene group and B is a carbonyl group when A and B are linked by a single bond, or A and B unite together to form a vinylene group when A and B are linked by a double bond, R 1 is a hydrogen atom, an alkyl group of 1 to 3 carbon atoms or a 2-hydroxyethyl group, R 2 and R 3 are hydrogen atoms, methyl groups or ethyl groups and may be identical to or different from each other, R 3 may be attached to the same carbon atom as R 2 , R 4 is a methyl or ethyl group, and X is a halogen atom; or a physiologically acceptable salt thereof, or a hydrate of the compound or the salt.
Claim 3
Dependent Claim
71 words
A benzo[ij]quinolizine-2-carboxylic acid derivative as claimed in claim 1 of the following general formula: ##STR23## Wherein R 1 is hydrogen, methyl, ethyl, n-propyl or 2-hydroxyethyl, R 2 is hydrogen or methyl, R 3 is hydrogen or methyl and may be attached to the same carbon atom as R 2 , R 4 is methyl or ethyl, and X is fluorine or chlorine; or a hydrate of a physiologically acceptable salt thereof.
Claim 4
Dependent Claim
65 words
A benzo[ij]quinolizine-2-carboxylic acid derivative as claimed in claim 1 of the following general formula: ##STR24## Wherein R 1 is hydrogen or methyl, R 2 is hydrogen or methyl, R 3 is hydrogen or methyl and may be attached to the same carbon atom as R 2 , R 4 is methyl or ethyl, and X is fluorine or chlorine; or a physiologically acceptable salt thereof.
Claim 5
Dependent Claim
2 words
9-Fluoro-5-methyl-8-(4-methyl-1-piperazinyl)-6,7-dihydro-1,7-dioxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid.
Claim 6
Dependent Claim
2 words
9-Fluoro-5-methyl-8-(4-methyl-1-piperazinyl)-6,7-dihydro-1,7-dioxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid.
Claim 7
Dependent Claim
2 words
9-Chloro-5-methyl-8-(4-ethyl-1-piperazinyl)-6,7-dihydro-1,7-dioxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid.
Claim 8
Dependent Claim
2 words
9-Chloro-5-methyl-8-(4-ethyl-1-piperazinyl)-6,7-dihydro-1,7-dioxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid.
Claim 9
Dependent Claim
2 words
9-Fluoro-5-methyl-8-(3,5-dimethyl-1-piperazinyl)-6,7-dihydro-1,7-dioxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid.
Claim 10
Dependent Claim
2 words
9-Fluoro-5-methyl-8-(3,5-dimethyl-1-piperazinyl)-6,7-dihydro-1,7-dioxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid.
Claim 11
Dependent Claim
2 words
9-Fluoro-5-methyl-8-(3,3-dimethyl-1-piperazinyl)-6,7-dihydro-1,7-dioxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid.
Claim 12
Dependent Claim
2 words
9-Fluoro-5-methyl-8-(3,3-dimethyl-1-piperazinyl)-6,7-dihydro-1,7-dioxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid.
Claim 13
Dependent Claim
2 words
9-Fluoro-5-methyl-8-(3-methyl-1-piperazinyl)-6,7-dihydro-1,7-dioxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid.
Claim 14
Dependent Claim
2 words
9-Fluoro-5-methyl-8-(3-methyl-1-piperazinyl)-6,7-dihydro-1,7-dioxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid.
Claim 15
Dependent Claim
2 words
9-Fluoro-5-methyl-8-(3,4-dimethyl-1-piperazinyl)-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid.
Claim 16
Dependent Claim
2 words
9-Fluoro-5-methyl-8-(3,4-dimethyl-1-piperazinyl)-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid.
Claim 17
Dependent Claim
3 words
9-Fluoro-5-methyl-8-(3-methyl-1-piperazinyl)-1-oxo-1H,5H-benzo[ij]W quinolizine-2-carboxylic acid.
Claim 18
Dependent Claim
3 words
9-Fluoro-5-methyl-8-(3-methyl-1-piperazinyl)-1-oxo-1H,5H-benzo[ij]W quinolizine-2-carboxylic acid.
Claim 19
Dependent Claim
2 words
9-Chloro-5-methyl-8-(3-methyl-1-piperazinyl)-1-oxo-1H,5H-benzo[]quinolizine-2-carboxylic acid.
Claim 20
Dependent Claim
2 words
9-Chloro-5-methyl-8-(3-methyl-1-piperazinyl)-1-oxo-1H,5H-benzo[]quinolizine-2-carboxylic acid.
Claim 21
Dependent Claim
5 words
9-Fluoro-5-methyl-8-(4-methyl-1-piperazinyl)-6, 7-dihydro-1,7-dioxo-1H,5H-benzo[]quinolizine-2-carboxylic acid hydrochloride monohydrate.
Claim 22
Dependent Claim
5 words
9-Fluoro-5-methyl-8-(4-methyl-1-piperazinyl)-6, 7-dihydro-1,7-dioxo-1H,5H-benzo[]quinolizine-2-carboxylic acid hydrochloride monohydrate.
Claim 23
Dependent Claim
5 words
9-Fluoro-5-methyl-8-(3,4-dimethyl-1-piperazinyl) -6,7-dihydro-1,7-dioxo-1H,5H-benzo[]quinolizine-2-carboxylic acid hydrochloride monohydrate.
Claim 24
Dependent Claim
5 words
9-Fluoro-5-methyl-8-(3,4-dimethyl-1-piperazinyl) -6,7-dihydro-1,7-dioxo-1H,5H-benzo[]quinolizine-2-carboxylic acid hydrochloride monohydrate.
Claim 25
Dependent Claim
27 words
A compound of claim 1 wherein A is a methylene group and B is a carbonyl group, and A and B are linked by a single bond.
Claim 26
Dependent Claim
11 words
A compound of claim 14 wherein X is flourine or chlorine.
Claim 27
Dependent Claim
28 words
A compound of claim 1 wherein A and B are united together to form a vinylene group in which A and B are linked by a double bond.
Claim 28
Dependent Claim
11 words
A compound of claim 16 wherein X is flourine or chlorine.
Claim 29
Dependent Claim
41 words
Method of using a compound or salt or hydrate of claim 1 for treating bacterial infection in a living subject which comprises administering to such a subject a therepeutically effective amount of such derivative or salt or hydrate of claim 1.
Claim 30
Dependent Claim
13 words
Method of claim 18 wherein the administering is carried out by oral administration.
References Cited (Backward Citations)
US4014877A
Cited
JPS5040616A
Cited
US4416884A
Cited
GB2086905A
Cited
GB2091726A
Cited
US4535161A
Cited
US4594347A
Cited
US4659734A
Cited
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