Glucopyranoside compound

1. A compound of Formula (I):

wherein

Ring A is

wherein R 1a , R 2a , R 3a , R 1b , R 2b , and R 3b are each independently a hydrogen atom, a halogen atom, a hydroxy group, an alkoxy group, an alkyl group, a haloalkyl group, a haloalkoxy group, a hydroxyalkyl group, an alkoxyalkyl group, an alkoxyalkoxy group, an alkenyl group, an alkynyl group, a cycloalkyl group, a cycloalkylidenemethyl group, a cycloalkenyl group, a cycloalkyloxy group, a phenyl group, a phenylalkoxy group, a cyano group, a nitro group, an amino group, a mono- or di-alkylamino group, an alkanoylamino group, a carboxyl group, an alkoxycarbonyl group, a carbamoyl group, a mono- or di-alkylcarbamoyl group, an alkanoyl group, an alkylsulfonylamino group, a phenylsulfonylamino group, an alkylsulfinyl group, an alkylsulfonyl group, or a phenylsulfonyl group, and

Ring B is

wherein R 4a is a phenyl group substituted by a halogen atom, a cyano group, an alkyl group, a haloalkyl group, an alkoxy group, a haloalkoxy group, an alkylenedioxy group, an alkyleneoxy group, or a mono- or di-alkylamino group; or a heterocyclyl group substituted by a halogen atom, a cyano group, an alkyl group, a haloalkyl group, an alkoxy group, or a haloalkoxy group, where the hererocyclyl group is a thienyl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyrazonyl group, a thiazonyl group, a quinolyl group, or a tetrazolyl group; R 5a is a hydrogen atom;

X is a carbon atom; and

Y is -(CH 2 ) n - (wherein n is 1 or 2);

or a pharmaceutically acceptable salt thereof.

2. The compound, or a pharmaceutically acceptable salt thereof according to claim 1 , wherein R 1a , R 2a , R 3a , R 1b , R 2b , and R 3b are each independently a hydrogen atom, a halogen atom, a lower alkyl group, a halo-lower alkyl group, a lower alkoxy group, or a phenyl group;

R 4a is a phenyl group substituted by halogen atom, a cyano group, a lower alkyl group, a halo-lower alkyl group, a lower alkoxy group, a halo-lower alkoxy group, a methylenedioxy group, an ethyleneoxy group, or a mono- or di-lower alkylamino group; or a heterocyclyl group substituted by a halogen atom, a cyano group, a lower alkyl group, or a lower alkoxy group.

3. The compound, or a pharmaceutically acceptable salt thereof according to claim 2 , wherein Ring A is

wherein R 1a is a halogen atom, a lower alkyl group, or a lower alkoxy group, and R 2a and R 3a are hydrogen atoms;

R 4a is a phenyl group substituted by a substituent selected from the group consisting of a halogen atom, a cyano group, a lower alkyl group, a halo-lower alkyl group, a lower alkoxy group, a halo-lower alkoxy group, and a mono- or di-lower alkylamino group; or a heterocyclyl group substituted by a halogen atom, a cyano group, a lower alkyl group, a lower alkoxy group, and Y is -CH 2 .

4. The compound, or a pharmaceutically acceptable salt thereof according to claim 3 , wherein R 4a is a phenyl group substituted by a halogen atom, a cyano group, a lower alkyl group, a halo-lower alkyl group, a lower alkoxy group, or a halo-lower alkoxy group; or a heterocyclyl group substituted by a halogen atom, a cyano group, a lower alkyl group, or a lower alkoxy group.

5. A compound represented by the following formula:

wherein R A is a halogen atom, or a lower alkyl group; and

Ring C is a phenyl group substituted by 1-3 substituents selected from the group consisting of a halogen atom, a cyano group, a lower alkyl group, a halo-lower alkyl group, a lower alkoxy group, a halo-lower alkoxy group, a methylenedioxy group, an ethyleneoxy group, a mono- or di-lower alkylamino group; or a heterocyclyl group substituted by 1-3 substituents selected from the group consisting of a halogen atom, a cyano group, a lower alkyl group, a halo-lower alkyl group, a lower alkoxy group, a halo-lower alkoxy group; where the heterocyclyl group is a thienyl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyrazolyl group, a thiazolyl group, a quinolyl group, or tetrazonyl group;

or a pharmaceutically acceptable salt thereof.

6. The compound, or a pharmaceutically acceptable salt thereof, according to claim 5 , wherein Ring C is a phenyl group substituted by 1-3 substituents selected from the group consisting of a halogen atom, a cyano group, a lower alkyl group, a halo-lower alkyl group, a lower alkoxy group, a halo-lower alkoxy group, and a mono- or di-lower alkylamino group; or a heterocyclyl group substituted by a substituent selected from the group consisting of a halogen atom, a cyano group, a lower alkyl group, a halo-lower alkyl group, a lower alkoxy group, and a halo-lower alkoxy group.

7. The compound, or a pharmaceutically acceptable salt thereof, according to claim 6 , wherein Ring C is a phenyl group substituted by a halogen atom, a cyano group, a lower alkyl group, a halo-lower alkyl group, a lower alkoxy group, or a halo-lower alkoxy group; or a heterocyclyl group substituted by a halogen atom, a cyano group, a lower alkyl group, or a lower alkoxy group.

8. The compound, or a pharmaceutically acceptable salt thereof, according to claim 5 , wherein Ring C is a phenyl group substituted by a halogen atom or a cyano group, or a pyridyl group substituted by a halogen atom.

9. The compound, according to claim 1 , wherein the compound is selected from the group consisting of:

1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethylyl]benzene;

1-(β-D-glucopyranosyl)-4-chloro-3-[5-(3-cyanophenyl)-2-thienylmethyl]benzene;

1-(β-D-glucopyranosyl)-4-chloro-3-[(5-(4-cyanophenyl)-2-thienylmethyl]benzene;

1-(β-D-glucopyranosyl)-4-methyl-3-[5-(6-fluoro-2-pyridyl)-2-thienylmethyl]benzene;

1-(β-D-glucopyranosyl)-4-chloro-3-[5-(6-fluoro-2-pyridyl)-2-thienylmethyl]benzene;

1-(β-D-glucopyranosyl)-4-methyl-3-[5-(3-difluoromethyl-phenyl)-2-thienylmethyl]benzene;

1-(β-D-glucopyranosyl)-4-methyl-3-[5-(3-cyanophenyl)-2-thienylmethyl]benzene;

1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-cyanophenyl)-2-thienylmethyl]benzene; and

1-(β-D-glucopyranosyl)-4-chloro-3-[5-(6-fluoro-3-pyridyl)-2-thienylmethyl]benzene;

or a pharmaceutically acceptable salt thereof.

10. 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(3-cyano-phenyl)-2-thienylmethyl]benzene, or a pharmaceutically acceptable salt thereof.

11. 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-cyano-phenyl)-2-thienylmethyl]benzene, or a pharmaceutically acceptable salt thereof.

12. 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluoro-phenyl)-2-thienylmethyl]benzene, or a pharmaceutically acceptable salt thereof.

13. 1-(β-D-glucopyranosyl)-4-chloro-3-[5-(3-cyano-phenyl)-2-thienylmethyl]benzene, or a pharmaceutically acceptable salt thereof.

14. 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(6-fluoro-2-pyridyl)-2-thienylmethyl]benzene, or a pharmaceutically acceptable salt thereof.

15. 1-(β-D-glucopyranosyl)-4-chloro-3-[5-(6-fluoro-2-pyridyl)-2-thienylmethyl]benzene, or a pharmaceutically acceptable salt thereof.

16. 1-(β-D-glucopyranosyl)-4-chloro-3-[5-(6-fluoro-3-pyridyl)-2-thienylmethyl]benzene, or a pharmaceutically acceptable salt thereof.

17. A pharmaceutical composition, which comprises the compound as set forth in claim 1 , or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier or diluent.

18. A process for preparing a compound of formula I:

wherein Ring A, Ring B, X and Y are as defined in claim 1 ,

which comprises deprotecting a compound of formula II:

wherein Ring A, Ring B and Y are defined in claim 1 R 11a is a hydrogen atom or a protecting group for a hydroxy group and R 11b , R 11c and R 11d are each independently a protecting group for a hydroxy group.

19. A process for preparing a compound of formula I-a:

wherein Ring A, Ring B and Y are as defined in claim 1 ,

which comprises reducing a compound of formula III:

wherein Ring A, Ring B and Y are as defined in claim 1 , and R 12 is a lower alkyl group.

20. A compound having the following structure:

21. A pharmaceutical composition which comprises the compound of claim 20 and a pharmaceutically acceptable carrier or diluent.

22. 1-(β-D-glucopyranosyl)-4-chloro-3-[5-(4-cyanophenyl)-2-thienylmethyl]benzene or a pharmaceutically acceptable salt thereof.

23. 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(3-difluoromethyl-phenyl)-2-thienylmethyl]benzene or a pharmaceutically acceptable salt thereof.

24. The compound, or a pharmaceutically acceptable salt thereof according to claim 1 , wherein Ring A is

wherein R 1a is a halogen atom, a hydroxy group, an alkoxy group, an alkyl group, a haloalkyl group, a haloalkoxy group, a hydroxyalkyl group, an alkoxyalkyl group, an alkoxyalkoxy group, an alkenyl group, an alkynyl group, a cycloalkyl group, a cycloalkylidenemethyl group, a cycloalkenyl group, a cycloalkyloxy group, a phenyl group, a phenylalkoxy group, a cyano group, a nitro group, an amino group, a mono- or di-alkylamino group, an alkanoylamino group, a carboxyl group, an alkoxycarbonyl group, a carbamoyl group, a mono- or di-alkylcarbamoyl group, an alkanoyl group, an alkylsulfonylamino group, a phenylsulfonylamino group, an alkylsulfinyl group, an alkylsulfonyl group, or a phenylsulfonyl group, and R 2a and R 3a are hydrogen.

25. The compound, or a pharmaceutically acceptable salt thereof according to claim 24 , wherein R 1a is a halogen atom or an alkyl group, and R 2a and R 3a are hydrogen.

26. The compound, or a pharmaceutically acceptable salt thereof according to claim 1 , wherein Ring A is

wherein R 1b , R 2b , and R 3b are as defined in claim 1 .