1. A compound of formula (I):
where
X is N or CH;
A represents a group of formula (a) or (b)
R1 represents a hydrogen atom or an \u2014NH2, \u2014NR3R4, \u2014NR3CO(C1-C4)Alk or \u2014NR3SO2(C1-C4)Alk group;
R2 represents a hydrogen or halogen atom or a (C1-C4)Alk, (C1-C4)alkoxy, \u2014COOH, \u2014COO(C1-C4)Alk, \u2014CN, \u2014CONR3R4, \u2014NO2, or \u2014NHSO2(C1-C4)Alk group;
m and n each represent 0, 1 or 2;
R3 and R4 each represent a hydrogen atom or a (C1-C4)Alk group;
Y1 and Y2 each represent NH or O;
or a salt or solvate thereof.
2. A compound as claimed in claim 1, where X represents CH.
3. A compound as claimed in claim 1, where X represents a nitrogen atom and the R2 group is in the 5-position.
4. A compound as claimed in claim 1, where the (C1-C4)Alk group is a methyl or ethyl group.
5. A compound as claimed in claim 1, where R2 is chosen from \u2014COOH, \u2014COO(C1-C4)Alk, \u2014CN, \u2014NO2, \u2014CONR3R4 and \u2014NHSO2-(C1-C4)Alk.
6. 3-1-(5-Ethoxycarbonylpyrid-2-yl)-4-piperidinylamino-1-(1,2-dihydro-2-oxobenzimidazol-4-yloxy)-2-propanol or a salt or solvate thereof.
7. 3-1-(5-Ethoxycarbonylpyrid-2-yl)-4-piperidinylamino-1-2-aminopyrid-5-yloxy-2-propanol or a salt or solvate thereof.
8. A process for the preparation of the compound of claim 1 wherein an epoxide of formula (II):
in which A\u2032 represents the group (a) or the group (b) in which R1 is optionally protected, where (a), (b) and R1 are as defined in claim 1, is reacted with an amine of formula (III)
where m, n, R2 and X are as indicated above, the protective group optionally present is removed and, optionally, the product of formula (I) thus obtained is converted into one of its salts or solvates.
9. A process for the preparation of the compound of claim 1 where A represents a group (b) and R1 is an NH2 group, wherein a product of formula (II) as defined in claim 8 where A\u2032 is the group (b) and R1 is a group of formula:
is reacted with an amine of formula III and the product of formula IV thus obtained:
is subjected to a hydrogenation reaction in order to convert the 4-nitrophenyldiazenyl group to an amino group and, optionally, the product of formula (I) thus obtained is converted into one of its salts or solvates.
10. A process for the preparation of the compound of claim 1 where A represents the group (a) and Y1 and Y2 represent a nitrogen atom, wherein a compound of formula (V):
is reacted with a compound of formula (III) as defined in claim 8, the nitro group of the product of formula (VI) thus obtained:
is reduced, the product of formula (VII) thus obtained:
is treated with a carbonylation agent, the product of formula (I) thus obtained is isolated and, optionally, is converted into one of its salts or solvates.
11. A process as claimed in claim 10 wherein the carbonylation agent is chosen from carbonyldiimidazole and phosgene.
12. A pharmaceutical composition comprising an effective amount of at least one compound of claim 1 as active principle.
13. A pharmaceutical composition comprising an effective amount of a compound according to claim 2.
14. A pharmaceutical composition comprising an effective amount of a compound according to claim 3.
15. A pharmaceutical composition comprising an effective amount of a compound according to claim 4.
16. A pharmaceutical composition comprising an effective amount of a compound according to claim 5.
17. A pharmaceutical composition comprising an effective amount of a compound according to claim 6.
18. A pharmaceutical composition comprising an effective amount of a compound according to claim 7.
19. A method for treating irritable bowel syndrome, for treating obesity, for treating diabetes, for treating glaucoma, for preventing or delaying premature labor, or for the treatment or prophylaxis of dysmenorrhea which comprises administering to a patient in need of such treatment an effective amount of a compound according to claim 1.
20. A method for treating irritable bowel syndrome, for treating obesity, for treating diabetes, for treating glaucoma, for preventing or delaying premature labor, or for the treatment or prophylaxis of dysmenorrhea which comprises administering to a patient in need of such treatment an effective amount of a compound according to claim 2.
21. A method for treating irritable bowel syndrome, for treating obesity, for treating diabetes, for treating glaucoma, for preventing or delaying premature labor, or for the treatment or prophylaxis of dysmenorrhea which comprises administering to a patient in need of such treatment an effective amount of a compound according to claim 3.
22. A method for treating irritable bowel syndromey, for treating obesity, for treating diabetes, for treating glaucoma, for preventing or delaying premature labor, or for the treatment or prophylaxis of dysmenorrhea which comprises administering to a patient in need of such treatment an effective amount of a compound according to claim 4.
23. A method for treating irritable bowel syndrome, for treating obesity, for treating diabetes, for treating glaucoma, for preventing or delaying premature labor, or for the treatment or prophylaxis of dysmenorrhea which comprises administering to a patient in need of such treatment an effective amount of a compound according to claim 5.
24. A method for treating irritable bowel syndrome, for treating obesity, for treating diabetes, for treating glaucoma, for preventing or delaying premature labor, or for the treatment or prophylaxis of dysmenorrhea which comprises administering to a patient in need of such treatment an effective amount of a compound according to claim 6.
25. A method for treating irritable bowel syndrome, for treating obesity, for treating diabetes, for treating glaucoma, for preventing or delaying premature labor, or for the treatment or prophylaxis of dysmenorrhea which comprises administering to a patient in need of such treatment an effective amount of a compound according to claim 7.
The claims below are in addition to those above.
All refrences to claim(s) which appear below refer to the numbering after this setence.
1. A rubber composition prepared by mixing, per 100 parts by mass of a rubber component comprising at least 50% by mass of a diene-based rubber, from 20 to 150 parts by mass of a filler, and from 0.05 to 30 parts by mass of a compound A which has an amidine structure represented by the following formula (I) and has a functional group reactive with the diene-based rubber.
2. The rubber composition according to claim 1, wherein the filler comprises, per 100 parts by mass of the rubber component, from 20 to 150 parts by mass of carbon black and from 0 to 130 parts by mass of an inorganic filler.
3. The rubber composition according to claim 1, wherein the functional group reactive with the diene-based rubber is at least one selected from a polysulfide group, a thiol group, a hydrazide group and a hydrazone group.
4. The rubber composition according to claim 1, wherein the amidine structure is a structure to form a hetero ring represented by the following formula (II-1) or (II-2):
5. The rubber composition according to claim 1, wherein the amidine structure is a structure not having a nitrogen-hydrogen bond (N\u2014H).
6. The rubber composition according to claim 1, wherein the amidine structure is a structure having an amide structure represented by the following formula (III):
7. The rubber composition according to claim 1, wherein the compound A is at least one selected from bis(1H-benzimidazol-1-yl)methyl disulfane, bis2-(1H-benzimidazol-1-yl)ethyl disulfane, bis2-(1H-benzimidazol-1-yl)propyl disulfane, bis2-(1H-benzimidazol-1-yl)butyl disulfane, bis2-(1H-benzimidazol-1-yl)pentyl disulfane, bis(1H-imidazol-1-yl)methyl disulfane, bis2-(1H-imidazol-1-yl)ethyl disulfane, bis2-(1H-imidazol-1-yl)propyl disulfane, bis2-(1H-imidazol-1-yl)butyl disulfane, bis2-(1H-imidazol-1-yl)pentyl disulfane, bis2-(1H-benzimidazol-1-yl)-2-oxoethyl disulfane, bis3-(1H-benzimidazol-1-yl)-3-oxopropyl disulfane, bis3-(1H-benzimidazol-1-yl)-3-oxobutyl disulfane, bis3-(1H-benzimidazol-1-yl)-3-oxopentyl disulfane, 2-(1H-benzimidazol-1-yl)acetohydrazide, bis(1H-benzimidazol-2-yl)methyl disulfane, bis2-(1H-benzimidazol-2-yl)ethyl disulfane, bis2-(1H-benzimidazol-2-yl)propyl disulfane, bis2-(1H-benzimidazol-2-yl)butyl disulfane, and bis2-(1H-benzimidazol-2-yl)pentyl disulfane.
8. A pneumatic tire using the rubber composition of claim 1.