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Details for Patent: 5,229,396

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Details for Patent: 5,229,396

Title: Anti-bacterial azabicyclo quinolone carboxylic acids
Abstract:Quinolone carboxylic acids 7-substituted by azabicyclo groups have antibacterial activity.
Inventor(s): Brighty; Katherine E. (Groton, CT)
Assignee: Pfizer Inc. (New York, NY)
Filing Date:Jul 24, 1992
Application Number:07/919,477
Claims:1. A compound of the formula ##STR17## or a pharmaceutically acceptable acid addition salt thereof, wherein R.sup.1 is hydrogen, a pharmaceutically acceptable cation, or (C.sub.1 -C.sub.6) alkyl;

Y when taken independently, is ethyl, t-butyl, vinyl, cyclopropyl, 2-fluoroethyl, p-fluorophenyl, or o,p-difluorophenyl;

W is hydrogen, fluoro, chloro, bromo, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, amino or aminomethyl;

A is CH, CF, CCl, COCH.sub.3, C--CH.sub.3, C--CN or N; and

R.sup.2 is ##STR18##

wherein R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.9, and R.sup.25 are each independently H, CH.sub.3, CH.sub.2 NH.sub.2, CH.sub.2 NHCH.sub.3 or CH.sub.2 NHC.sub.2 H.sub.5, and R.sup.5, R.sup.6, R.sup.7, and R.sup.9 may also independently be NH.sub.2, NHCH.sub.3 or NHC.sub.2 H.sub.5, provided that not more than three of R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.9, and R.sup.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.

2. A compound according to claim 1 wherein R.sup.1 is hydrogen.

3. A compound according to claim 1 wherein Y is cyclopropyl or o,p-difluorophenyl.

4. A compound according to claim 1 wherein W is hydrogen and A is CH or N.

5. A compound according to claim 1 wherein W is hydrogen and A is N.

6. A compound according to claim 5 wherein one or two of R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.9, and R.sup.25 are other than hydrogen.

7. A compound according to claim 6 wherein one of R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, or R.sup.9, is CH.sub.2 NH or CH.sub.2 NHCH.sub.3, and optionally, another of R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.9, or R.sup.25 is methyl.

8. A compound according to claim 7 wherein one of R.sup.5, R.sup.6, R.sup.7 or R.sup.9 is NH.sub.2 or NHCH.sub.3 and, optionally, another of R.sup.5, R.sup.6, R.sup.7 or R.sup.9 or one of R.sup.3, R.sup.4, or R.sup.25 is methyl.

9. A compound according to claim 8, wherein R.sup.6, R.sup.7 or R.sup.9 is amino and, optionally one of R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.9, or R.sup.25 is methyl.

10. A compound according to claim 9 wherein R.sup.7 is amino and, optionally, one of R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.9, or R.sup.25 is methyl.

11. A compound according to claim 6 wherein R.sup.7 is amino and R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.9, or R.sup.25 are each hydrogen.

12. A compound according to claim 1, wherein said compound is

7-([1.alpha., 6.alpha., 7.alpha.]-7-Amino-3-azabicyclo[4.1.0]hept-3-yl)-6-fluoro-1-(2,4-difluoroph enyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid,

7-([1.alpha., 6.alpha., 7.alpha.]-7-Amino-3-azabicyclo[4.1.0]-hept-3-yl)-1-cyclopropyl-6-fluoro-1, 4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid, or

7-(1-amino-3-azabicyclo[4.1.0]hept-3-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro -4-oxo-quinoline-3-carboxylic acid.

13. An antibacterial composition comprising an antibacterially effective amount of a compound according to claim 1 and a pharmaceutically acceptable carrier.

14. 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.

15. A compound according to claim 1 wherein R.sup.6, R.sup.7 or R.sup.9 contains an amino group which is covalently bonded through a peptide bond to one amino acid residue.

16. A compound according to claim 1 wherein R.sup.6, R.sup.7 or R.sup.9 contains an amino group which is covalently bonded through a peptide bond to a polypeptide of two or more amino acids.

17. A compound according to claim 1 wherein R.sup.6, R.sup.7 or R.sup.9 contains an amino group which is covalently bonded through a peptide bond to a polypeptide of two amino acids.

18. A compound according to claim 11 wherein the amino group of R.sup.7 is covalently bonded through a peptide bond to one amino acid residue.

19. A compound according to claim 11 wherein the amino group of R.sup.7 is covalently bonded through a peptide bond to a polypeptide of two or more amino acids.

20. A compound according to claim 11 wherein the amino group of R.sup.7 is covalently bonded through a peptide bond to a polypeptide of two amino acids.
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