Claims
- 1. A pyrroloquinoline compound or salt thereof having the formula: ##STR16## wherein R.sup.1 is a C.sub.1 -C.sub.6 alkyl group; R.sup.2 is a group: ##STR17## or a group: ##STR18## wherein R.sup.3, R.sup.4 and R.sup.5 are the same or different, a hydrogen atom or a C.sub.1 -C.sub.6 alkyl group, and R.sup.6 is an amino group or a C.sub.1 -C.sub.6 alkylamino-C.sub.1 -C.sub.6 alkyl group, X.sup.1 is a halogen atom and * denotes an asymmetric atom, wherein said asymmetric carbon atom of pyrroloquinoline ring has S-configuration.
- 2. A pyrroloquinoline compound or salt thereof having the formula: ##STR19## wherein R.sup.1 is a C.sub.1 -C.sub.6 alkyl group; R.sup.2 is a group: ##STR20## or a group: ##STR21## wherein R.sup.3, R.sup.4 and R.sup.5 are the same or different, a hydrogen atom or a C.sub.1 -C.sub.6 alkyl group, and R.sup.6 is an amino group or a C.sub.1 -C.sub.6 alkylamino-C.sub.1 -C.sub.6 alkyl group, X.sup.1 is a halogen atom and * denotes an asymmetric atom, wherein said asymmetric carbon atom of pyrroloquinoline ring has R-configuration.
- 3. A pyrroloquinoline compound or salt thereof according to claim 1, wherein R.sup.2 is a group: ##STR22## wherein R.sup.3 and R.sup.5 are the same or different, a hydrogen atom or a C.sub.1 -C.sub.6 alkyl group.
- 4. A pyrroloquinoline compound or salt thereof according to claim 1, wherein R.sup.2 is a group: ##STR23## wherein R.sup.3 and R.sup.5 are the same or different, a hydrogen atom or a C.sub.1 -C.sub.6 alkyl group, and R.sup.41 is a C.sub.1 -C.sub.6 alkyl group.
- 5. A pyrroloquinoline compound or salt thereof according to claim 1, wherein R.sup.2 is a group: ##STR24## wherein R.sup.6 is an amino group or a C.sub.1 -C.sub.6 alkylamino-C.sub.1 -C.sub.6 alkyl group.
- 6. A pyrroloquinoline compound or salt thereof according to claim 3, wherein alkyl group is methyl group or ethyl group, and X.sup.1 is a fluorine atom or a chlorine atom.
- 7. A pyrroloquinoline compound or salt thereof according to claim 6, wherein X.sup.1 is a fluorine atom.
- 8. A pyrroloquinoline compound or salt thereof according to claim 6, wherein alkyl group is methyl group, and X.sup.1 is a chlorine atom.
- 9. A pyrroloquinoline compound or salt thereof according to claim 7, wherein alkyl group is methyl group.
- 10. A pyrroloquinoline salt according to claim 9.
- 11. A pyrroloquinoline compound according to claim 9.
- 12. A pyrroloquinoline salt according to claim 8.
- 13. A pyrroloquinoline compound according to claim 8.
- 14. A pyrroloquinoline salt according to claim 4.
- 15. A pyrroloquinoline compound according to claim 4.
- 16. A pyrroloquinoline salt thereof according to claim 14, wherein alkyl group is methyl group, and X.sup.1 is a fluorine atom.
- 17. A pyrroloquinoline compound thereof according to claim 15, wherein alkyl group is methyl group, and X.sup.1 is a fluorine atom.
- 18. A pyrroloquinoline salt thereof according to claim 16, wherein one of R.sup.3 and R.sup.5 is a hydrogen atom.
- 19. A pyrroloquinoline salt thereof according to claim 16, wherein R.sup.3 and R.sup.5 are C.sub.1 -C.sub.6 alkyl groups.
- 20. A pyrroloquinoline compound or salt thereof according to claim 5, wherein R.sup.1 is methyl group, and X.sup.1 is a fluorine atom.
- 21. A pyrroloquinoline salt according to claim 20.
- 22. A pyrroloquinoline compound according to claim 20.
- 23. A racemic pyrroloquinoline compound or salt thereof having the formula: ##STR25## wherein X.sup.1 is a fluorine atom, R.sup.1 is a methyl group, and R.sup.9 is a group: ##STR26## wherein R.sup.31 is a methyl group or an ethyl group;
- 24. A racemic pyrroloquinoline compound or salt thereof having the formula: ##STR27## wherein X.sup.1 is a fluorine atom, R.sup.1 is methyl group, and R.sup.9 is a group: ##STR28## wherein R.sup.10 is a C.sub.1 -C.sub.6 alkylamino-C.sub.1 -C.sub.6 group.
- 25. The compound of claim 3 selected from the group consisting of (+)-8-fluoro-2-(S)-methyl-9-(3-methyl-1-piperazinyl)-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid hydrochloride.
- (+)-8-chloro-2-(S)-methyl-9-(3-methyl-1-piperazinyl)-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid hydrochloride,
- (+)-8-fluoro-2-(S)-methyl-9-(3,5-dimethyl-1-piperazinyl)-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid hydrochloride,
- (-)-8-fluoro-2-(S)-methyl-9-(3-(S)-methyl-1-piperazinyl)-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid hydrochloride and
- (+)-8-fluoro-2-(S)-methyl-9-(3-(R)-methyl-1-piperazinyl)-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid hydrochloride.
- 26. The compound of claim 4 selected from the group consisting of (+)-8-fluoro-2-(S)-methyl-9-(4-methyl-1-piperazinyl)-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid,
- (+)-8-fluoro-2-(S)-methyl-9-(4-methyl-1-piperazinyl)-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid hydrochloride,
- (+)-8-fluoro-2-(S)-methyl-9-(3,4-dimethyl-1-piperazinyl)-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylicacid,
- (+)-8-fluoro-2-(S)-methyl-9-(3,4-dimethyl-1-piperazinyl)-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid hydrochloride,
- (+)-8-fluoro-2-(S)-methyl-9-(3,4,5-trimethyl-1-piperazinyl)-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid,
- (+)-8-fluoro-2-(S)-methyl-9-(3,4,5-trimethyl-1-piperazinyl)-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid hydrochloride,
- (+)-8-fluoro-2-(S)-methyl-9-((3S)-3,4-dimethyl-1-piperazinyl)-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid and
- (+)-8-fluoro-2-(S)-methyl-9-((3S)-3,4-dimethyl-1-piperazinyl)-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid hydrochloride.
- 27. The compound of claim 5 selected from the group consisting of (+)-8-fluoro-2-(S)-methyl-9-(3-amino-1-pyrrolidinyl)-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid,
- (+)-8-fluoro-2-(S)-methyl-9-(3-amino-1-pyrrolidinyl)-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid hydrochloride,
- (+)-8-fluoro-2(S)-methyl-9-[3-(ethylaminomethyl)-1-pyrrolidinyl]-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5carboxylic acid and
- (+)-8-fluoro-2(S)-methyl-9-[3-(isopropylaminomethyl)-1-pyrrolidinyl]-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid hydrochloride.
- 28. The compound of claim 3 selected from the group consisting of (+)-8-fluoro-2-(S)-methyl-9-(3-methyl-1-piperazinyl)-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid hydrochloride,
- (-)-8-fluoro-2-(S)-methyl-9-(3-(S)-methyl-1-piperazinyl)-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid hydrochloride and
- (+)-8-fluoro-2-(S)-methyl-9-(3-(R)-methyl-1-piperazinyl)-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid hydrochloride.
- 29. The compound of claim 4 selected from the group consisting of (+)-8-fluoro-2-(S)-methyl-9-(3,4-dimethyl-1-piperazinyl)-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid,
- (+)-8-fluoro-2-(S)-methyl-9-(3,4-dimethyl-1-piperazinyl)-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid hydrochloride,
- (+)-8-fluoro-2-(S)-methyl-9-((3S)-3,4-dimethyl-1-piperazinyl)-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]wuiniline-5-carboxylic acid and
- (+)-8-fluoro-2-(S)-methyl-9-((3S)-3,4-dimethyl-1-piperazinyl)-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid hydrochloride.
- 30. A pharmaceutical composition for antimicrobial use comprising a therapeutically effective amount of a pyrroloquinoline compound or salt thereof defined in claim 2, and a pharmaceutically acceptable carrier.
- 31. A pharmaceutical composition for antimicrobial use comprising a therapeutically effective amount of a pyrroloquinoline compound or salt thereof defined in claim 1, and a pharmaceutically acceptable carrier.
- 32. A pharmaceutical composition for antimicrobial use comprising a therapeutically effective amount of a pyrroloquinoline compound or salt thereof defined in claim 23 or 24, and a pharmaceutically acceptable carrier.
- 33. A pharmaceutical composition for antimicrobial use comprising a therapeutically effective amount of a pyrroloquinoline compound or salt thereof defined in claim 3, and a pharmaceutically acceptable carrier.
- 34. A pharmaceutical composition for antimicrobial use comprising a therapeutically effective amount of a pyrroloquinoline compound or salt thereof defined in claim 4, and a pharmaceutically acceptable carrier.
- 35. A pharmaceutical composition for antimicrobial use comprising a therapeutically effective amount of a pyrroloquinoline compound or salt thereof defined in claim 28, and a pharmaceutically acceptable carrier.
- 36. A pharmaceutical composition for antimicrobial use comprising a therapeutically effective amount of a pyrroloquinoline compound or salt thereof defined in claim 29, and a pharmaceutically acceptable carrier.
Priority Claims (2)
Number |
Date |
Country |
Kind |
1-78786 |
Mar 1989 |
JPX |
|
2-262906 |
Sep 1990 |
JPX |
|
CROSS REFERENCE TO RELATED APPLICATION
This application is a continuation-in-part of Ser. No. 07/500,355 filed on Mar. 28, 1990, now abandoned.
Foreign Referenced Citations (4)
Number |
Date |
Country |
0390135 |
Oct 1990 |
EPX |
56-30964 |
Mar 1981 |
JPX |
59-78189 |
May 1984 |
JPX |
62-252790 |
Nov 1987 |
JPX |
Continuation in Parts (1)
|
Number |
Date |
Country |
Parent |
500355 |
Mar 1990 |
|