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US4550104A
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Antibacterial thiazolo-quinolines and thiazolo-naphthyridines
Assignee: Warner Lambert Co LLC
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Filing: 1984-07-20
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Granted: 1985-10-29
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Expires: 2004-07-20
Abstract
Abstract Novel 7-fluoro-8-heterocyclyl-5-oxo-5H-thiazolo (3,2-a)-naphthyridine- and quinoline- 4-carboxylic acids as antibacterial agents are described as well as methods for their manufacture, formulation, and use in treating bacterial infections.
Inventors
- 👤 Thomas F. Mich
- 👤 Joseph P. Sanchez
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 22:52
CPC Classifications
C; C07; C07D; C07D207/00; C07D207/02; C07D207/18; C07D207/22; C07D207/24; C07D207/26; C07D207/273; C07D207/277; C07D207/04; C07D207/08; C07D207/09; C07D207/10; C07D207/14; C07D487/00; C07D487/02; C07D487/10; C07D513/00; C07D513/02; C07D513/04
Claims Analysis
Total Claims: 35
Claim 1
Independent Claim
164 words
A compound of the formula ##STR16## wherein Z is ##STR17## X is CH, CF, or N; Y is hydrogen or amino; n is 1, 2, 3, or 4; n' is 1, 2, 3, or 4 wherein n+n' is a total of 2, 3, 4, or 5, and n" is 0, 1, or 2; R is hydrogen or methyl; R 1 is hydrogen, alkyl having from one to six carbon atoms or a cation; R 3 is hydrogen, alkyl having from one to four carbon atoms or cycloalkyl having three to six carbon atoms; R 4 is hydrogen, alkyl from one to four carbon atoms, hydroxyalkyl having two to four carbon atoms, trifluoroethyl, or R 7 CO- wherein R 7 is alkyl having from one to four carbon atoms or alkoxy having from one to four carbon atoms; R 5 and R 6 are each hydrogen or alkyl having from one to three carbon atoms, and the pharmaceutically acceptable acid addition or base salts thereof.
Claim 2
Dependent Claim
164 words
A compound of the formula ##STR16## wherein Z is ##STR17## X is CH, CF, or N; Y is hydrogen or amino; n is 1, 2, 3, or 4; n' is 1, 2, 3, or 4 wherein n+n' is a total of 2, 3, 4, or 5, and n" is 0, 1, or 2; R is hydrogen or methyl; R 1 is hydrogen, alkyl having from one to six carbon atoms or a cation; R 3 is hydrogen, alkyl having from one to four carbon atoms or cycloalkyl having three to six carbon atoms; R 4 is hydrogen, alkyl from one to four carbon atoms, hydroxyalkyl having two to four carbon atoms, trifluoroethyl, or R 7 CO- wherein R 7 is alkyl having from one to four carbon atoms or alkoxy having from one to four carbon atoms; R 5 and R 6 are each hydrogen or alkyl having from one to three carbon atoms, and the pharmaceutically acceptable acid addition or base salts thereof.
Claim 3
Dependent Claim
11 words
A compound as claimed in claim 1 wherein Y is hydrogen.
Claim 4
Dependent Claim
13 words
A compound as claimed in claim 2, wherein X is CF or N.
Claim 5
Dependent Claim
19 words
A compound as claimed in claim 2, wherein R 1 is hydrogen or a pharmaceutically acceptable base salt thereof.
Claim 6
Dependent Claim
11 words
A compound as claimed in claim 3, wherein Z is ##STR18##
Claim 7
Dependent Claim
11 words
A compound as claimed in claim 3, wherein Z is ##STR19##
Claim 8
Dependent Claim
52 words
A compound as claimed in claim 1, wherein Y is hydrogen; Z is ##STR20## in which n" is 0 or 1 and R 3 is hydrogen, methyl, ethyl, 1- or 2-propyl; X is N or C-F; R is hydrogen or methyl, R 1 is hydrogen or a pharmaceutically acceptable base salt thereof.
Claim 9
Dependent Claim
46 words
A compound as claimed in claim 1, wherein Y is hydrogen; Z is ##STR21## X is C-F or N; R is hydrogen or methyl; R 3 is hydrogen, methyl, or ethyl, and R 1 is hydrogen or a pharmaceutically acceptable acid addition or base salt thereof.
Claim 10
Dependent Claim
11 words
A compound as claimed in claim 1 and being 7-fluoro-8-[3-[(ethylamino)methyl]-1-pyrrolidinyl]-5-oxo-1,2-dihydro-5H-thiazolo[3,2-a]quinoline-4-carboxylic acid.
Claim 11
Dependent Claim
11 words
A compound as claimed in claim 1 and being 7-fluoro-8-(3-amino-1-pyrrolidinyl)-5-oxo-1,2-dihydro-5H-thiazolo[3,2-a]quinoline-4-carboxylic acid.
Claim 12
Dependent Claim
11 words
A compound as claimed in claim 1 and being 7-fluoro-8-[[3-(methylamino)methyl]-1-pyrrolidinyl]-5-oxo-1,2-dihydro-5H-thiazolo[3,2-a]quinoline-4-carboxylic acid.
Claim 13
Dependent Claim
11 words
A compound as claimed in claim 1 and being 7-fluoro-8-[3-[[(2-hydroxyethyl)amino]methyl]-1-pyrrolidinyl]-5-oxo-1,2-dihydro-5H-thiazolo-[3,2-a]quinoline-4-carboxylic acid.
Claim 14
Dependent Claim
11 words
A compound as claimed in claim 1 and being 7-fluoro-8-[3-(aminomethyl)-1-pyrrolidinyl]-5-oxo-1,2-dihydro-5H-thiazolo[3,2-a]quinoline-4-carboxylic acid.
Claim 15
Dependent Claim
11 words
A compound as claimed in claim 1 and being 7-fluoro-8-[[3-(propylamino)methyl]-1-pyrrolidinyl]-5-oxo-1,2-dihydro-5H-thiazolo[3,2-a]quinoline-4-carboxylic acid.
Claim 16
Dependent Claim
11 words
A compound as claimed in claim 1 and being 7-fluoro-8-[3-[[(2,2,2-trifluoroethyl)amino]methyl]-1-pyrrolidinyl]-5-oxo-1,2-dihydro-5H-thiazolo[3,2-a]quinoline-4-carboxylic acid.
Claim 17
Dependent Claim
11 words
A compound as claimed in claim 1 and being 7-fluoro-8-[[3-(2-propylamino)methyl]-1-pyrrolidinyl]-5-oxo-1,2-dihydro-5H-thiazolo[3,2-a]quinoline-4-carboxylic acid.
Claim 18
Dependent Claim
11 words
A compound as claimed in claim 1 and being 7-fluoro-8-[[3-(cyclopropylamino)methyl]-1-pyrrolidinyl]-5-oxo-1,2-dihydro-5H-thiazolo[3,2-a]quinoline-4-carboxylic acid.
Claim 19
Dependent Claim
11 words
A compound as claimed in claim 1 and being 7-fluoro-8-[2,7-diazaspiro[4,4]non-2-yl]-5-oxo-1,2-dihydro-5H-thiazolo[3,2-a]quinoline-4-carboxylic acid.
Claim 20
Dependent Claim
11 words
A compound as claimed in claim 1 and being 7-fluoro-8-(7-methyl-2,7-diazaspiro[4,4]non-2-yl)-5-oxo-1,2-dihydro-5H-thiazolo[3,2-a]quinoline-4-carboxylic acid.
Claim 21
Dependent Claim
11 words
A compound as claimed in claim 1 and being 7-fluoro-8-(7-ethyl-2,7-diazaspiro[4,4]non-2-yl)-5-oxo-1,2-dihydro-5H-thiazolo[3,2-a]quinoline-4-carboxylic acid.
Claim 22
Dependent Claim
11 words
A compound as claimed in claim 1 and being 8-(3-amino-1-pyrrolidinyl)-7-fluoro-1,2-dihydro-5-oxo-5H-thiazolo-[3,2-a][1,6]-naphthyridine-4-carboxylic acid.
Claim 23
Dependent Claim
11 words
A compound as claimed in claim 1 and being 7-fluoro-1-methyl-8-(3-amino-1-pyrrolidinyl)-5-oxo-1,2-dihydro-5H-thiazolo[3,2-a]quinoline-4-carboxylic acid.
Claim 24
Dependent Claim
11 words
A compound as claimed in claim 1 and being 7-fluoro-1-methyl-8-[3-[(ethylamino)methyl]-1-pyrrolidinyl]-5-oxo-1,2-dihydro-5H-thiazolo[3,2-a]quinoline-4-carboxylic acid.
Claim 25
Dependent Claim
11 words
A compound as claimed in claim 1 and being 7-fluoro-1-methyl-8-[3-[[(2-hydroxyethyl)amino]methyl]-1-pyrrolidinyl]-5-oxo-1,2-dihydro-5H-thiazolo[3,2-a]quinoline-4-carboxylic acid.
Claim 26
Dependent Claim
11 words
A compound as claimed in claim 1 and being 7-fluoro-1-methyl-8-[3-(aminomethyl)-1-pyrrolidinyl]-5-oxo-1,2-dihydro-5H-thiazolo[3,2-a]quinoline-4-carboxylic acid.
Claim 27
Dependent Claim
11 words
A compound as claimed in claim 1 and being 7-fluoro-1-methyl-8-[[3-(propylamino)methyl]-1-pyrrolidinyl]-5-oxo-1,2-dihydro-5H-thiazolo-[3,2-a]quinoline-4-carboxylic acid.
Claim 28
Dependent Claim
11 words
A compound as claimed in claim 1 and being 7-fluoro-1-methyl-8-[[3-(2-propylamino)methyl]-1-pyrrolidinyl]-5-oxo-1,2-dihydro-5H-thiazolo-[3,2-a]quinoline-4-carboxylic acid.
Claim 29
Dependent Claim
11 words
A compound as claimed in claim 1 and being 7-fluoro-1-methyl-8-[3-[[(2,2,2-trifluoroethyl)amino]methyl]-1-pyrrolidinyl]-5-oxo-1,2-dihydro-5H-thiazolo[3,2-a]quinoline-4-carboxylic acid.
Claim 30
Dependent Claim
11 words
A compound as claimed in claim 1 and being 7-fluoro-1-methyl-8-[2,7-diazaspiro[4,4]non-2-yl]-5-oxo-1,2-dihydro-5H-thiazolo[3,2-a]quinoline-4-carboxylic acid.
Claim 31
Dependent Claim
11 words
A compound as claimed in claim 1 and being 7-fluoro-1-methyl-8-(7-methyl-2,7-diazaspiro-[4,4]non-2-yl)-5-oxo-1,2-dihydro-5H-thiazolo-[3,2-a]quinoline-4-carboxylic acid.
Claim 32
Dependent Claim
11 words
A compound as claimed in claim 1 and being 7-fluoro-1-methyl-8-(7-ethyl-2,7-diazaspiro-[4,4]non-2-yl)-5-oxo-1,2-dihydro-5H-thiazolo-[3,2-a]quinoline-4-carboxylic acid;
Claim 33
Dependent Claim
11 words
A compound as claimed in claim 1 and being 7-fluoro-1-methyl-8-[3-[(cyclopropylamino)-methyl]-1-pyrrolidinyl]-5-oxo-1,2-dihydro-5H-thiazolo[3,2a]quinoline-4-carboxylic acid.
Claim 34
Dependent Claim
22 words
A pharmaceutical composition comprising an antibacterially effective amount of a compound as claimed in claim 1 together with a pharmaceutically acceptable carrier.
Claim 35
Dependent Claim
22 words
The method of treating bacterial infections in mammals which comprises administering to said mammal a pharmaceutical composition as claimed in claim 33.
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) | 1988-10-28 | 1989-04-29 | 1989-10-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-10-28 | 1993-04-29 | 1993-10-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-10-28 | 1997-04-29 | 1997-10-29 | $7700.00 | Window Closed / Lapsed |