US5164402A
Expired / Lapsed
US
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Azabicyclo quinolone and naphthyridinone carboxylic acids
Assignee: Pfizer Inc
•
Filing: 1991-02-04
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Granted: 1992-11-17
•
Expires: 2011-02-04
Abstract
Abstract Quinolone carboxylic acids 7-substituted by azabicyclo groups have antibacterial activity.
Inventors
- 👤 Katherine E. Brighty
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 18:49
CPC Classifications
C; C07; C07D; C07D401/00; C07D401/02; C07D401/04; C07D209/00; C07D209/02; C07D209/52; C07D471/00; C07D471/02; C07D471/04; C07K; C07K5/00; C07K5/04; C07K5/06; C07K5/06191
Claims Analysis
Total Claims: 28
Claim 1
Independent Claim
200 words
A compound of the formula ##STR17## or a pharmaceutically acceptable acid addition salt thereof, wherein R 1 is hydrogen, a pharmaceutically acceptable cation, or (C 1 -C 6 ) alkyl; Y is ethyl, vinyl, cyclopropyl, 2-fluoroethyl, p-fluorophenyl, or o,p-difluorophenyl; W is hydrogen, fluoro, chloro, bromo, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, amino or aminomethyl; A is CH, CR, CCl, COCH 3 , C--CH 3 , C--CN or N; and R 2 ##STR18## wherein R 3 , R 6 , R 7 , R 9 , R 10 , and R 25 are each independently H, CH 3 , CH 2 NH 2 , CH 2 NHCH 3 or CH 2 NHC 2 H 5 , and R 6 , R 7 , and R 9 may also independently be NH 2 , NHCH 3 or NHC 2 H 5 , provided that not more than three of R 3 , R 6 , R 7 , R 9 , R 10 and R 25 are other than hydrogen and if three of these substituents are not hydrogen, at least one of them is methyl; and prodrugs of those compounds of formula I having free amino groups.
Claim 2
Dependent Claim
200 words
A compound of the formula ##STR17## or a pharmaceutically acceptable acid addition salt thereof, wherein R 1 is hydrogen, a pharmaceutically acceptable cation, or (C 1 -C 6 ) alkyl; Y is ethyl, vinyl, cyclopropyl, 2-fluoroethyl, p-fluorophenyl, or o,p-difluorophenyl; W is hydrogen, fluoro, chloro, bromo, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, amino or aminomethyl; A is CH, CR, CCl, COCH 3 , C--CH 3 , C--CN or N; and R 2 ##STR18## wherein R 3 , R 6 , R 7 , R 9 , R 10 , and R 25 are each independently H, CH 3 , CH 2 NH 2 , CH 2 NHCH 3 or CH 2 NHC 2 H 5 , and R 6 , R 7 , and R 9 may also independently be NH 2 , NHCH 3 or NHC 2 H 5 , provided that not more than three of R 3 , R 6 , R 7 , R 9 , R 10 and R 25 are other than hydrogen and if three of these substituents are not hydrogen, at least one of them is methyl; and prodrugs of those compounds of formula I having free amino groups.
Claim 3
Dependent Claim
11 words
A compound according to claim 1 wherein R 1 is hydrogen.
Claim 4
Dependent Claim
12 words
A compound according to claim 1 wherein Y is cyclopropyl or o,p-difluorophenyl.
Claim 5
Dependent Claim
16 words
A compound according to claim 1 wherein W is hydrogen, and A is CH or N.
Claim 6
Dependent Claim
14 words
A compound according to claim 1 wherein W is hydrogen and A is N.
Claim 7
Dependent Claim
32 words
A compound according to claim 1 wherein one or two of R 3 , R 6 , R 7 , R 9 , R 10 and R 25 are other than hydrogen.
Claim 8
Dependent Claim
58 words
A compound according to claim 6 wherein one of R 3 , R 6 , R 7 , R 9 , or R 10 is CH 2 NH 2 or CH 2 NHCH 3 , and another of R 3 , R 6 , R 7 , R 9 , R 10 or R 25 may be methyl.
Claim 9
Dependent Claim
49 words
A compound according to claim 6 wherein one of R 6 , R 7 , or R 9 is NH 2 or NHCH 3 and another of R 6 , R 7 or R 9 or one of R 3 , R 10 or R 25 may be methyl.
Claim 10
Dependent Claim
40 words
A compound according to claim 8 wherein R 6 , R 7 or R 9 is amino and one of R 3 , R 6 , R 7 , R 9 , R 10 or R 25 may be methyl.
Claim 11
Dependent Claim
31 words
A compound according to claim 9 wherein R 7 is amino and one of R 3 , R 6 , R 9 , R 10 or R 25 may be methyl.
Claim 12
Dependent Claim
29 words
A compound according to claim 6 wherein R 7 is amino and R 3 , R 6 , R 9 , R 10 or R 25 are each hydrogen.
Claim 13
Dependent Claim
19 words
A compound according to claim 1, wherein said compound is 7-(1-amino-3-azabicyclo[3.1.0]hex-3-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid, 7-([1α,2β,5α,6α]-6-amino-2-methyl-3-azabicyclo[3.1.0π-hex-3-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid, 7-([1α,6α,6α]-6-[(N-methyl)amino]-3-azabicyclo[3.1.0]hex-3-yl(-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid, or 7-([1α,5α,6α]-6-aminomethyl-3-azabicyclo[3.1.0]-hex-3-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid.
Claim 14
Dependent Claim
20 words
A compound according to claim 1, wherein said compound is 7-([1α,5α,6α]-6-amino-3-azabicyclo[3.1.0]hex-3-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid, 7-([1α,5α,6α]-6-amino-3-azabicyclo[3.1.0]hex-3-yl(-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid, p-toluenesulfonic acid salt, or 7-([1α,5α,6β]-6-amino-3-azabicyclo[3.1.0]hex-3-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid.
Claim 15
Dependent Claim
16 words
A compound according to claim 1 wherein said compound is 7-([1α,5α,6α]-6-amino-3-azabicyclo[3.1.0]hex-3-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid, or 7-([1α,5α,6α]-6-amino-3-azabicyclo[3.1.0]hex-3-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid, hydrate.
Claim 16
Dependent Claim
21 words
A compound according to claim 1 wherein said compound is 7-([1α,5α,6α -6-amino-3-azabicyclo[3.1.0]hex-3-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid, hydrochloride salt, or 7-([1α,5α,6α]-6-amino-3-azabicyclo[3.1.0]hex-3-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid, methanesulfonic acid salt.
Claim 17
Dependent Claim
32 words
A compound according to claim 1 wherein R 6 , R 7 or R 9 contains an amino group which is covalently bonded through a peptide bond to one amino acid residue.
Claim 18
Dependent Claim
36 words
A compound according to claim 1 wherein R 6 , R 7 or R 9 contains an amino group which is covalently bonded through a peptide bond to a polypeptide of two or more amino acids.
Claim 19
Dependent Claim
34 words
A compound according to claim 1 wherein R 6 , R 7 or R 9 contains an amino group which is covalently bonded through a peptide bond to a polypeptide of two amino acids.
Claim 20
Dependent Claim
25 words
A compound according to claim 11 wherein the amino group of R 7 is covalently bonded through a peptide bond to one amino acid residue.
Claim 21
Dependent Claim
29 words
A compound according to claim 11 wherein the amino group of R 7 is covalently bonded rough a peptide bond to a polypeptide of two or more amino acids.
Claim 22
Dependent Claim
27 words
A compound according to claim 11 wherein the amino group of R 7 is covalently bonded through a peptide bond to a polypeptide of two amino acids.
Claim 23
Dependent Claim
15 words
A compound according to claim 11 wherein said compound is 7-([1α,5α,6α]-6-(L-Ala-amino)-3-azabicyclo[3.1.0]hex-3-yl-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-1, 8-naphthyridine-3-carboxylic acid, hydrochloride salt.
Claim 24
Dependent Claim
14 words
A compound according to claim 21 wherein said compound is 7-([1α,5α,6α]-6-(L-Ala-L-Leu-amino)-3-azabicyclo[3.1.0]-hex-3-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid hydrochloride salt.
Claim 25
Dependent Claim
20 words
A compound according to claim 21 wherein said compound is 7-([1α,5α,6α]-6-(L-Ala-L-Ala-amino)-3-azabicyclo[3.1.0]hex-3-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid, hydrochloride salt, or 7-([1α,5α,6α]-6-(L-Ala-L-Ala-amino)-3-azabicyclo[3.1.0]hex-3-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid, methanesulfonic acid salt.
Claim 26
Dependent Claim
12 words
A compound according to claim 21 wherein said compound is 7-([1α,5α,6α]-6(L-Ala-L-Ala-amino)-3-azabicyclo[3.1.0]hex-3-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid.
Claim 27
Dependent Claim
20 words
An antibacterial composition comprising an antibacterially effective amount of a compound according to claim 1 and a pharmaceutically acceptable carrier.
Claim 28
Dependent Claim
31 words
A method for the treatment of a bacterial infection which comprises administering to a subject affected by a bacterial infection an antibacterially effective amount of a compound according to claim 1.
References Cited (Backward Citations)
US4851418A
Cited
JPS6456673A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1995-11-17 | 1996-05-18 | 1996-11-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1999-11-17 | 2000-05-18 | 2000-11-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2003-11-17 | 2004-05-18 | 2004-11-17 | $7700.00 | Window Closed / Lapsed |