Substituted pyrrolidine derivative
A quinolone antibacterial compound, or a salt or hydrate of the compound, for the treatment of infectious diseases, which exhibit potent antibacterial activity and higher selective toxicity against Gram-positive and Gram-negative bacteria, which do not cause side effects (e.g., convulsion), which exhibit higher safety, and which has a structure of formula (I):
1. A compound of formula (I):
wherein
R 1 represents a hydrogen atom, a C 1 -C 6 alkyl group, or a substituted carbonyl group derived from an amino acid, a dipeptide, or a tripeptide;
R 2 represents a hydrogen atom or a C 1 -C 6 alkyl group, and, when either one or each of R 1 and R 2 is an alkyl group, the alkyl group may be substituted with a group selected from the group consisting of a hydroxyl group, an amino group, a halogen atom, a C 1 -C 6 alkylthio group, and a C 1 -C 6 alkoxy group;
R 3 represents a C 2 -C 6 alkyl group, a C 2 -C 6 alkenyl group, or a C 3 -C 6 cycloalkyl group;
R 4 and R 5 each independently represents a hydrogen atom or a C 1 -C 6 alkyl group;
R 6 represents a C 3 -C 6 halogenocycloalkyl group;
R 7 represents a hydrogen atom, a phenyl group, an acetoxymethyl group, a pivaloyloxymethyl group, an ethoxycarbonyl group, a choline group, a dimethylaminoethyl group, a 5-indanyl group, a phthalidyl group, a 5-alkyl-2-oxo-1,3-dioxol-4-ylmethyl group, a 3-acetoxy-2-oxobutyl group, a C 1 -C 6 alkyl group, a C 2 -C 7 alkoxymethyl group, or a phenylalkyl group formed of a C 1 -C 6 alkylene group and a phenyl group;
X 1 represents a hydrogen atom or a halogen atom; and
A represents a nitrogen atom or a partial structure represented by the following formula (II):
wherein X 2 represents a C 1 -C 6 alkyl group or a C 1 -C 6 alkoxy group; a salt, or a hydrate thereof.
2. The compound as described in claim 1 , a salt, or a hydrate thereof, wherein the compound of formula (I) is a compound represented by the following formula:
wherein
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , X 1 , and A are as defined in claim 1 .
3. The compound as described in claim 1 , a salt, or a hydrate thereof, wherein each of R 1 and R 2 in formula (I) is a hydrogen atom.
4. The compound as described in claim 1 , a salt, or a hydrate thereof, wherein one of R 1 and R 2 in formula (I) is a hydrogen atom, and the other is a methyl group.
5. The compound as described in claim 1 , a salt, or a hydrate thereof, wherein R 3 in formula (I) is an ethyl group, an n-propyl group, a vinyl group, an isopropyl group, or a cyclopropyl group.
6. The compound as described in claim 1 , a salt, or a hydrate thereof, wherein R 3 in formula (I) is an ethyl group.
7. The compound as described in claim 1 , a salt, or a hydrate thereof, wherein each of R 4 and R 5 in formula (I) is a hydrogen atom.
8. The compound as described in claim 1 , a salt, or a hydrate thereof, wherein X 1 in formula (I) is a fluorine atom.
9. The compound as described in claim 1 , a salt, or a hydrate thereof, wherein R 7 in formula (I) is a hydrogen atom.
10. The compound as described in claim 1 , a salt, or a hydrate thereof, wherein A in formula (I) is a C-methyl group or a C-methoxy group.
11. The compound as described in claim 1 , a salt, or a hydrate thereof, wherein R 6 in formula (I) is a 1,2-cis-2-halogenocyclopropyl group.
12. The compound as described in claim 1 , a salt, or a hydrate thereof, wherein R 6 in formula (I) is a stereochemically single 1,2-cis-2-halogenocyclopropyl group.
13. The compound as described claim 1 , a salt, or a hydrate thereof, wherein R 6 in formula (I) is a (1R,2S)-2-fluorocyclopropyl group.
14. The compound as described in claim 1 , a salt, or a hydrate thereof, wherein a compound of formula (I) is a stereochemically single compound.
15. 7-[(3S,4S)-3-Amino-4-ethylpyrrolidine-1-yl]-6-fluoro-1-[(1R,2S)-2-fluorocyclopropyl]-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylic acid, a salt, or a hydrate thereof.
16. 7-[(3S,4S)-3-Amino-4-ethylpyrrolidine-1-yl]-6-fluoro-1-[(1R,2S)-2-fluorocyclopropyl]-1,4-dihydro-8-methyl-4-oxoquinoline-3-carboxylic acid, a salt, or a hydrate theroef.
17. A drug containing, as an active ingredient, the compound as recited in claim 1 , a salt, or a hydrate thereof.
18. An antibacterial drug containing, as an active ingredient, the compound as recited in claim 1 , a salt, or a hydrate thereof.
19. An infectious disease treating drug containing, as an active ingredient, the compound as recited in claim 1 , a salt, or a hydrate thereof.