Claims
- 1. A compound of the formula: ##STR12## in which R is hydrogen, aklyl of one to three carbon atoms, hydroxyalkyl of two or three carbon atoms, benzyl, or p-amino-benzyl; R.sup.1 is hydrogen or alkanoyl of from one to three carbon atoms; X is CH, CF, or N; Y is hydrogen, fluoro, or amino; R.sub.1 is hydrogen, alkyl having from one to six carbon atoms or a cation; R.sub.2 is alkyl having from one to four carbon atoms, vinyl haloalkyl, hydroxyalkyl having from two to four carbon atoms or cycloalkyl having three to six carbon atoms, or a pharamaceutically acceptable acid addition or base salt thereof.
- 2. A compound as claimed in claim 1, wherein Y is hydrogen.
- 3. A compound as claimed in claim 2, wherein R.sub.2 is ethyl, vinyl, 2-fluoroethyl or cyclopropyl.
- 4. A compound as claimed in claim 3, wherein X is Cf, or N.
- 5. A compound as claimed in claim 4, wherein R.sub.1 is hydrogen or a pharmaceutically acceptable base salt thereof.
- 6. A compound as claimed in claim 1 and being 7-(2,5-diazabicyclo[2.2.2]oct-2-yl)-1-ethyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid.
- 7. A compound as claimed in claim 1 and being 7-(2,5-diazabicyclo[2.2.2]oct-2-yl)-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid.
- 8. A compound as claimed in claim 1 and being 7-(2,5-diazabicyclo[2.2.2]oct-2-yl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid.
- 9. A compound as claimed in claim 1 and being 7-(2,5-diazabicyclo[2.2.2]oct-2-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid.
- 10. A compound as claimed in claim 1 and being 7-[3-(exo-amino)-8-azabicyclo[3.2.1]oct-8-yl]-1-ethyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid.
- 11. A compound as claimed in claim 1 and being 7-[3-(exo-amino)-8-azabicyclo[3.2.1]oct-8-yl]-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid.
- 12. A compound as claimed in claim 1 and being 7-[3-(exo-amino)-8-azabicyclo[3.2.1]oct-8-yl]-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid.
- 13. A compound as claimed in claim 1 and being 7-[3-(exo-amino)-8-azabicyclo[3.2.1]oct-8-yl]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid.
- 14. A compound as claimed in claim 1 and being 7-(1,4-diazabicyclo[3.2.1]oct-4-yl)-1-ethyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid.
- 15. A compound as claimed in claim 1 and being 7-(1,4-diazabicyclo[3.2.1]oct-4-yl)-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid.
- 16. A compound as claimed in claim 1 and being 7-(1,4-diazabicyclo[3.2.1]oct-4-yl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid.
- 17. A compound as claimed in claim 1 and being 7-(1,4-diazabicylo[3.2.1]oct-4-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid.
- 18. A compound as claimed in claim 1 being 1-cyclopropyl-6-fluoro-1,4-dihydro-7-(5-methyl-2,5-diazabicyclo[2.2.1]hept-2-yl)-4-oxo-1,8-naphthyridine-3-carboxylic acid.
- 19. A compound as claimed in claim 1 and being 1-cyclopropyl-6,8-difluoro-1,4-dihydro-7-(5-methyl-2,5-diazabicyclo[2.2.1]hept-2-yl)-4-oxo-3-quinolinecarboxylic acid.
- 20. A compound as claimed in claim 1 and being 7.degree.-2,5-diazabicyclo(2.2.1)hept-2-yl]-1-ethyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid.
- 21. A compound as claimed in claim 1 and being 7-[2,5-diazabicyclo(2.2.1)hept-2-yl]-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid.
- 22. A compound as claimed in claim 1 and being 1-cyclopropyl-7-[2,5-diazabicyclo(2.2.1)hept-2-yl]-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid.
- 23. A compound as claimed in claim 1 and being 1-cyclopropyl-7-[2,5-diazabicyclo(2.2.1)hept-2-yl]-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid.
- 24. A compound as claimed in claim 1 and being 1-ethyl-6-fluoro-7-(5-methyl-2,5-diazabicyclo-[2.2.2]oct-2-yl)-1,4-dihydro-4-oxo-1,8-naphthyridine 3-carboxylic acid.
- 25. A compound as claimed in claim 1 and being 1-ethyl 6,8-difluoro-7-(5-methyl-2,5-diazabicyclo-[2.2.1]hept-2-yl)-4-oxo-3-quinolinecarboxylic acid.
- 26. A compound as claimed in claim 1 and being 1-ethyl 7-(5-ethyl-2,5-diazabicyclo[2.2.1]hept-2-yl]-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid.
- 27. A compound as claimed in claim 1 and being 1-ethyl-7-[5-(1-methylethyl)-2,5-diazabicyclo-[2.2.1]hept-2-yl]-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid.
- 28. A compound as claimed in claim 1 and being 1-ethyl-6,8-difluoro-1,4-dihydro-7-[5-(2-hydroxyethyl)-2,5-diazabicyclo[2.2.1]hept-2-yl[-4-oxo-3-quinolinecarboxylic acid.
- 29. A compound as claimed in claim 1 and being 7-[5-(4-aminophenyl)methyl]-2,5-diazabicyclo-[2.2.2]oct-2-yl-1-cyclopropyl-6-fluoro-1,5-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid.
- 30. A compound as claimed in claim 1 and being 7-[5-[(4-aminophenyl)methyl]-2,5-diazabicyclo-[2.2.1]hept-2-yl]-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid.
- 31. A pharmaceutical composition comprising an antibacterially effective amount of a compound as claimed in claim 1 together with a pharmaceutically acceptable carrier.
- 32. The method of treating bacterial infections in mammals which comprises administering to said mammal a pharmaceutical composition as claimed in claim 31.
CROSS-REFERENCE TO RELATED APPLICATION
This is a continuation-in-part of U.S. Ser. No. 600,934, filed Apr. 16, 1984, and now abandoned.
US Referenced Citations (8)
Foreign Referenced Citations (6)
Number |
Date |
Country |
47005 |
Mar 1982 |
EPX |
106489 |
Apr 1984 |
EPX |
149286 |
Sep 1982 |
JPX |
203085 |
Dec 1982 |
JPX |
72589 |
Apr 1983 |
JPX |
109181 |
Dec 1983 |
JPX |
Non-Patent Literature Citations (2)
Entry |
Koga et al., J. Med. Chem., 23, (1980), pp. 1358-1363. |
Rufer et al., Eur. J. Med. Chem.-Chimica Therapeutica, 29, (1977), pp. 27-29. |
Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
600934 |
Apr 1984 |
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