Claims
- 1. A compound of the formula (I) ##STR23## or a pharmaceutically acceptable salt thereof wherein R.sup.1 is hydrogen, straight or branch chain lower alkyl or phenyl unsubstituted or substituted by one or two halo moieties; R.sup.2 is hydrogen or straight or branch chain lower alkyl; and R.sup.3 is hydrogen, halo or straight or branch chain lower alkoxy.
- 2. A compound according to claim 1 wherein R.sup.1 is hydrogen, straight or branch chain alkyl of 1 to 4 carbon atoms, phenyl or halophenyl.
- 3. A compound according to claim 1 wherein R.sup.2 is hydrogen or straight or branch chain alkyl of 1 to 4 carbon atoms.
- 4. A compound according to claim 1 wherein R.sup.3 is hydrogen, halo or straight or branch chain alkoxy of 1 to 4 carbon atoms.
- 5. A compound according to claim 1 wherein R.sup.1 is hydrogen, straight or branch chain alkyl of 1 to 4 carbon atoms, phenyl or halophenyl; R.sup.2 is hydrogen or straight or branch chain alkyl of 1 to 4 carbon atoms; and R.sup.3 is hydrogen, halo or straight or branch chain alkoxy of 1 to 4 carbon atoms.
- 6. A compound according to claim 1 wherein R.sup.1 is hydrogen, straight or branch chain alkyl of 1 to 4 carbon atoms, phenyl or fluorophenyl; R.sup.2 is hydrogen or straight or branch chain alkyl of 1 to 4 carbon atoms; and R.sup.3 is hydrogen, fluoro or straight or branch chain alkoxy of 1 to 4 carbon atoms.
- 7. A compound according to claim 1 in the form of a pharmaceutically acceptable salt.
- 8. The compound according to claim 1 which is ethyl 6-fluoro-1-methyl-7-[4-(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl-1-piperazinyl]-4-oxo-4H-[1,3-]thiazeto[3,2-a]quinoline-3-carboxylate, 6-fluoro-1-methyl-7-([4-(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl-1-piperazinyl]-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid, 6-fluoro-1-methyl-7-[4-(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl-1-piperazinyl]-4-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid hydrochloride, 6-fluoro-1-methyl-7-[4-(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl-1-piperazinyl]-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid methanesulfonate, 6-fluoro-7-[4-(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl-1-piperazinyl]-4-oxo-1-phenyl-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid, ethyl 6-fluoro-7-[4-(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl-1-piperazinyl]-4-oxo-1-phenyl-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate, 6,8-difluoro-7-[4-(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl-1-piperazinyl]-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid, 6,8-difluoro-1-methyl-7-[4-(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl-1-piperazinyl]-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid, 6,8-difluoro-7-[4-(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl-1-piperazinyl]-4-oxo-1-phenyl-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid, 6,8-difluoro-1-(4-fluorophenyl)-7-[4-(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl-1-piperazinyl]-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid, 6,8-difluoro-1-(2,4-difluorophenyl)-7-[4-(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl-1-piperazinyl]-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid, 6,8-difluoro-1-(3,4-difluorophenyl)-7-[4-(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl-1-piperazinyl]-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid, 6-fluoro-8-methoxy-7-[4-(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl-1-piperazinyl]-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid, 6-fluoro-8-methoxy-1-methyl-7-[4-(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl-1-piperazinyl]-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid or 6-fluoro-8-methoxy-7-[4-(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl-1-piperazinyl]-4-oxo-1-phenyl-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid.
- 9. A pharmaceutical composition useful for treating bacterial infections in humans and animals which comprises an antibacterially effective amount of a compound of the formula (I) ##STR24## or a pharmaceutically acceptable salt thereof wherein R.sup.1 is hydrogen, straight or branch chain lower alkyl or phenyl unsubstituted or substituted by one or two halo moieties; R.sup.2 is hydrogen or straight or branch chain lower alkyl; and R.sup.3 is hydrogen, halo or straight or branch chain lower alkoxy, in combination of the pharmaceutically acceptable carrier.
- 10. A composition according to claim 9 wherein R.sup.1 is hydrogen, straight or branch chain alkyl of 1 to 4 carbon atoms, phenyl or halophenyl.
- 11. A composition according to claim 9 wherein R.sup.2 is hydrogen or straight or branch chain alkyl of 1 to 4 carbon atoms.
- 12. A composition according to claim 9 wherein R.sup.3 is hydrogen, halo or straight or branch chain alkoxy of 1 to 4 carbon atoms.
- 13. A composition according to claim 9 wherein R.sup.1 is hydrogen, straight or branch chain alkyl of 1 to 4 carbon atoms, phenyl or halophenyl; R.sup.2 is hydrogen or straight or branch chain alkyl of 1 to 4 carbon atoms; and R.sup.3 is hydrogen, halo or straight or branch chain alkoxy of 1 to 4 carbon atoms.
- 14. A composition according to claim 9 wherein R.sup.1 is hydrogen, straight or branch chain alkyl of 1 to 4 carbon atoms, phenyl or fluorophenyl; R.sup.2 is hydrogen or straight or branch chain alkyl of 1 to 4 carbon atoms; and R.sup.3 is hydrogen, fluoro or straight or branch chain alkoxy of 1 to 4 carbon atoms.
- 15. A composition according to claim 9 wherein the compound is in the form of a pharmaceutically acceptable salt.
- 16. A composition according to claim 9 wherein the compound is ethyl 6-fluoro-1-methyl-7-[4-(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl-1-piperazinyl]-4-oxo-4H-[1,3-]thiazeto[3,2-a]quinoline-3-carboxylate,6-fluoro-1-methyl-7-([4-(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl-1-piperazinyl]-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3carboxylic acid, 6-fluoro-1-methyl-7-[4-(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl-1-piperazinyl]-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid hydrochloride, 6-fluoro-1-methyl-7-[4-(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl-1-piperazinyl]-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid methanesulfonate,6-fluoro-7-[4-(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl-1-piperazinyl]-4-oxo-1-phenyl-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid, ethyl 6-fluoro-7-[4-(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl-1-piperazinyl]-4-oxo-1-phenyl-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate, 6,8-difluoro-7-[4-(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl-1-piperazinyl]-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid, 6,8-difluoro-1-methyl-7-[4-(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl-1-piperazinyl]-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid, 6,8-difluoro-7-[4-(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl-1-piperazinyl]-4-oxo-1-phenyl-4H-[1,3]-thiazeto[3,2-a]quinoline-3-carboxylic acid, 6,8-difluoro-1-(4-fluorophenyl)-7-[4-(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl-1-piperazinyl]-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid, 6,8-difluoro-1-(2,4-difluorophenyl)-7-[4-(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl-1-piperazinyl]-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid, 6,8-difluoro-1-(3,4-difluorophenyl)-7-[4-(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl-1-piperazinyl]-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid, 6-fluoro-8-methoxy-7-[4-(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl-1-piperazinyl]-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid, 6-fluoro-8-methoxy-1-methyl-7-[4-(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl-1-piperazinyl]-4-oxo-4H-[1,3]-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid or 6-fluoro-8-methoxy-7-[4-(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl-1-piperazinyl]-4-oxo 4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid.
- 17. A method of treating bacterial infections in humans and animals which comprises administering to human or animal in need thereof an antibacterially effective amount of a compound of the formula (I) ##STR25## or a pharmaceutically acceptable salt thereof wherein R.sup.1 is hydrogen, straight or branch chain lower alkyl or phenyl unsubstituted or substituted by one or two halo moieties; R.sup.2 is hydrogen or straight or branch chain lower alkyl; and R.sup.3 is hydrogen, halo or straight or branch chain lower alkoxy, in combination of the pharmaceutically acceptable carrier.
- 18. A method according to claim 17 wherein R.sup.1 is hydrogen, straight or branch chain alkyl of 1 to 4 carbon atoms, phenyl or halophenyl.
- 19. A method according to claim 17 wherein R.sup.2 is hydrogen or straight or branch chain alkyl of 1 to 4 carbon atoms.
- 20. A method according to claim 17 wherein R.sup.3 is hydrogen, halo or straight or branch chain alkoxy of 1 to 4 carbon atoms.
- 21. A method according to claim 17 wherein R.sup.1 is hydrogen, straight or branch chain alkyl of 1 to 4 carbon atoms, phenyl or halophenyl; R.sup.2 is hydrogen or straight or branch chain alkyl of 1 to 4 carbon atoms; and R.sup.3 is hydrogen, halo or straight or branch chain alkoxy of 1 to 4 carbon atoms.
- 22. A method according to claim 17 wherein R.sup.1 is hydrogen, straight or branch chain alkyl of 1 to 4 carbon atoms, phenyl or fluorophenyl; R.sup.2 is hydrogen or straight or branch chain alkyl of 1 to 4 carbon atoms; and R.sup.3 is hydrogen, fluoro or straight or branch chain alkoxy of 1 to 4 carbon atoms.
- 23. A method according to claim 17 wherein the compound is in the form of a pharmaceutically acceptable salt.
- 24. A method according to claim 17 wherein the compound is ethyl 6-fluoro-1-methyl-7-[4-(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl-1-piperazinyl]-4-oxo-4H-[1,3-]thiazeto[3,2-a]quinoline-3-carboxylate,6-fluoro-1-methyl-7-([4-(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl-1-piperazinyl]-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid, 6-fluoro-1-methyl-7-[4-(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl-1-piperazinyl]-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid hydrochloride, 6-fluoro-1-methyl-7-[4-(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl-1-piperazinyl]-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid methanesulfonate,6-fluoro-7-[4-(5-methyl-2-oxo-1,3-dioxolen-4 -yl) methyl-1-piperazinyl]-4 -oxo-1-phenyl-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid, ethyl 6-fluoro-7-[4-(5-methyl-2-oxo-1,3 dioxolen-4-yl)methyl-1-piperazinyl]-4-oxo-1-phenyl-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate, 6,8-difluoro-7-[4-(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl-1-piperazinyl]-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid, 6,8-difluoro-1-methyl-7-[4-(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl-1-piperazinyl]-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid, 6,8-difluoro-7-[4-(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl-1-piperazinyl]-4-oxo-1-phenyl-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid, 6,8-difluoro-1-(4-fluorophenyl)-7-[4-(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl-1-piperazinyl]-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid, 6,8-difluoro-1-(2,4-difluorophenyl)-7-[4-(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl-1-piperazinyl]-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid, 6,8-difluoro-1-(3,4-difluorophenyl)-7-[4-(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl-1-piperazinyl]-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid, 6-fluoro-8-methoxy-7-[4-(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl-1-piperazinyl]-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid, 6-fluoro-8-methoxy-1-methyl-7-[4-(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl-1-piperazinyl]-4-oxo-4H-[1,3]-thiazeto[3,2-a]quinoline-3-carboxylic acid or 6-fluoro-8-methoxy-7-[4-(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl-1-piperazinyl]-4-oxo-1-phenyl-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid.
Priority Claims (1)
Number |
Date |
Country |
Kind |
62-281550 |
Nov 1987 |
JPX |
|
Parent Case Info
This is a continuation of Ser. No. 267,940 filed Nov. 7 1988, now abandoned.
US Referenced Citations (7)
Foreign Referenced Citations (2)
Number |
Date |
Country |
51-203067 |
Dec 1982 |
JPX |
0227887 |
Dec 1984 |
JPX |
Non-Patent Literature Citations (1)
Entry |
Derwent Abstract of Japan 0227887. |
Continuations (1)
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Number |
Date |
Country |
Parent |
267940 |
Nov 1988 |
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