Ester or amide derivatives
View Patent ↗An ester or amide derivative represented by the general formula (I) or a pharmaceutically acceptable salt thereof. Particularly, an ester or amide derivative of 4-oxo-1,4-dihydroqunoline-2-carboxylic acid represented by the general formula (I′) or (I″), or a pharmaceutically acceptable salt thereof.
1. An ester compound of formula (I) or a pharmaceutically acceptable salt thereof, wherein formula (I) is:
wherein:
X 1 to X 4 each independently represents C or N, provided that at least three of X 1 to X 4 represents C;
Y represents O;
R 1 represents a C 1 to C 6 alkyl group;
R 2 represents (a) a C 3 to C 10 alkyl group, or (b) an aryl-C 1 to C 10 alkyl group and that the aryl may be substituted with from one to three of halogen, C 1 to C 6 alkyl, C 1 to C 6 alkyl-O—, nitro, cyano, amino, hydroxycarbonyl, C 1 to C 6 alkyl-NH—, or di-C 1 to C 6 alkyl=N—;
R 3 represents H, a C 1 to C 6 alkyl group, an aryl-C 1 to C 6 alkyl group, a heteroaryl-C 1 to C 6 alkyl group, a cycloalkyl-C 1 to C 6 alkyl group, an aryl group, a heteroaryl group, or a cycloalkyl group, provided that the aryl, heteroaryl, and cycloalkyl group may each be substituted with from one to three of halogen, C 1 to C 6 alkyl, C 1 to C 6 alkyl-O—, nitro, cyano, amino, hydroxycarbonyl, C 1 to C 6 alkyl-NH—, or di-C 1 to C 6 alkyl=N—; and
R 4 to R 7 may be the same or different and each represents H, a halogen, a nitro group, a cyano group, an amino group, a hydroxycarbonyl group, a C 1 to C 6 alkyl group, a C 1 to C 6 alkyl-O— group, a C 1 to C 6 alkyl-NH group, or a di-C 1 to C 6 alkyl=N— group,
provided that in the case where X 1 to X 4 each represents N, R 4 to R 7 to be bound thereto are not present and that R 3 and R 4 may be taken together to form a linear or branched C 1 to C 8 alkylene which may be inserted by N, O or S.
2. The ester compound or its pharmaceutically acceptable salt according to claim 1 , wherein X 1 to X 4 are all C.
3. The ester compound or its pharmaceutically acceptable salt according to claim 1 , wherein R 3 is H.
4. The ester compound or its pharmaceutically acceptable salt according to claim 1 , wherein R 2 represents (a) C 5 to C 10 alkyl group, or (b) a phenyl-C 1 to C 6 alkyl group, provided that the phenyl may be substituted with from one to three of halogen, C 1 to C 6 alkyl, C 1 to C 6 alkyl-O—, nitro, amino, C 1 to C 6 alkyl-NH—, or di-C 1 to C 6 alkyl=N—.
5. The ester compound or its pharmaceutically acceptable salt according to claim 4 , wherein R 2 represents (a) a C 6 to C 8 alkyl group or (b) a benzyl group which may be substituted with from one to three of halogen, C 1 to C 6 alkyl, C 1 to C 6 alkyl-O—, nitro, amino, C 1 to C 6 alkyl-NH—, or di-C 1 to C 6 alkyl=N—.
6. The ester compound or its pharmaceutically acceptable salt according to claim 1 , wherein R 1 represents a methyl group.
7. The ester compound or its pharmaceutically acceptable salt according to claim 1 , wherein R 4 to R 7 are all H.
8. The ester compound or its pharmaceutically acceptable salt according to claim 1 , which is Benzyl 3-methyl-4-oxo-1,4-dihydroquinoline-2-carboxylate, or a salt thereof.
9. A pharmaceutical composition comprising an ester compound according to claim 1 or its pharmaceutically acceptable salt and a pharmaceutically acceptable carrier.
10. The ester compound or its pharmaceutically acceptable salt according to claim 2 , wherein R 3 is H.
11. The ester compound or its pharmaceutically acceptable salt according to claim 10 , wherein R 2 represents (a) a C 5 to C 10 alkyl group, or (b) a phenyl-C 1 to C 6 alkyl group, provided that the phenyl may be substituted with from one to three of halogen, C 1 to C 6 alkyl, C 1 to C 6 alkyl-O—, nitro, amino, C 1 to C 6 alkyl-NH—, or di-C 1 to C 6 alkyl=N—.
12. The ester compound or its pharmaceutically acceptable salt according to claim 11 , wherein R 2 represents (a) a C 6 to C 8 alkyl group or (b) a benzyl group which may be substituted with from one to three of halogen, C 1 to C 6 alkyl, C 1 to C 6 alkyl-O—, nitro, amino, C 1 to C 6 alkyl-NH—, or di-C 1 to C 6 alkyl=N—.
13. The ester compound or its pharmaceutically acceptable salt according to claim 11 , wherein R 1 represents a methyl group.
14. The ester compound or its pharmaceutically acceptable salt according to claim 13 , wherein R 4 to R 7 are all H.
15. The ester compound or its pharmaceutically acceptable salt according to claim 2 , wherein R 2 represents (a) a C 5 to C 10 alkyl group, or (b) a phenyl-C 1 to C 6 alkyl group, provided that the phenyl may be substituted with from one to three of halogen, C 1 to C 6 alkyl, C 1 to C 6 alkyl-O—, nitro, amino, C 1 to C 6 alkyl-NH—, or di-C 1 to C 6 alkyl=N—.
16. The ester compound or its pharmaceutically acceptable salt according to claim 15 , wherein R 2 represents (a) a C 6 to C 8 alkyl group or (b) a benzyl group which may be substituted with from one to three of halogen, C 1 to C 6 alkyl, C 1 to C 6 alkyl-O—, nitro, amino, C 1 to C 6 alkyl-NH—, or di-C 1 to C 6 alkyl=N—.
17. The ester compound or its pharmaceutically acceptable salt according to claim 2 , wherein R 1 represents a methyl group.
18. The ester compound or its pharmaceutically acceptable salt according to claim 2 , wherein R 4 to R 7 are all H.
19. The ester compound or its pharmaceutically acceptable salt according to claim 3 , wherein R 2 represents (a) a C 5 to C 10 alkyl group, or (b) a phenyl-C 1 to C 6 alkyl group, provided that the phenyl may be substituted with from one to three of halogen, C 1 to C 6 alkyl, C 1 to C 6 alkyl-O—, nitro, amino, C 1 to C 6 alkyl-NH—, or di-C 1 to C 6 alkyl=N—.
20. The ester compound or its pharmaceutically acceptable salt according to claim 19 , wherein R 2 represents (a) a C 6 to C 8 alkyl group or (b) a benzyl group which may be substituted with from one to three of halogen, C 1 to C 6 alkyl, C 1 to C 6 alkyl-O—, nitro, amino, C 1 to C 6 alkyl-NH—, or di-C 1 to C 6 alkyl=N—.
21. The ester compound or its pharmaceutically acceptable salt according to claim 3 , wherein R 1 represents a methyl group.
22. The ester compound or its pharmaceutically acceptable salt according to claim 3 , wherein R 4 to R 7 are all H.
23. The ester compound or its pharmaceutically acceptable salt according to claim 4 , wherein R 1 represents a methyl group.
24. The ester compound or its pharmaceutically acceptable salt according to claim 4 , wherein R 4 to R 7 are all H.
25. The ester compound or its pharmaceutically acceptable salt according to claim 5 , wherein R 1 represents a methyl group.
26. The ester compound or its pharmaceutically acceptable salt according to claim 5 , wherein R 4 to R 7 are all H.
27. The ester compound or its pharmaceutically acceptable salt according to claim 6 , wherein R 4 to R 7 are all H.