Claims for Patent: 7,943,788

Summary for Patent: 7,943,788

Title:	Glucopyranoside compound
Abstract:	A compound of the formula: ##STR00001## wherein Ring A and Ring B are: (1) Ring A is an optionally substituted unsaturated monocyclic heterocyclic ring, and Ring B is an optionally substituted unsaturated monocyclic heterocyclic ring, an optionally substituted unsaturated fused heterobicyclic ring, or an optionally substituted benzene ring, (2) Ring A is an optionally substituted benzene ring, and Ring B is an optionally substituted unsaturated monocyclic heterocyclic ring or an optionally substituted unsaturated fused heterobicyclic ring, or (3) Ring A is an optionally substituted unsaturated fused heterobicyclic ring, and Ring B are independently an optionally substituted unsaturated monocyclic heterocyclic ring, an optionally substituted unsaturated fused heterobicyclic ring, or an optionally substituted benzene ring; X is a carbon atom or a nitrogen atom; Y is --(CH.sub.2).sub.n-- (n is 1 or 2); a pharmaceutically acceptable salt thereof, or a prodrug thereof.
Inventor(s):	Nomura; Sumihiro (Kawaguchi, JP), Kawanishi; Eiji (Kitamoto, JP), Ueta; Kiichiro (Wako, JP)
Assignee:	Mitsubishi Tanabe Pharma Corporation (Osaka-shi, JP)
Application Number:	11/045,446
Patent Litigation and PTAB cases:	See patent lawsuits and PTAB cases for patent 7,943,788
Patent Claims:	1. A compound of Formula (I): ##STR00400## wherein Ring A is ##STR00401## wherein R.sup.1a, R.sup.2a, R.sup.3a, R.sup.1b, R.sup.2b, and R.sup.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 ##STR00402## wherein R.sup.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.sup.5a is a hydrogen atom; X is a carbon atom; and Y is -(CH.sub.2).sub.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.sup.1a, R.sup.2a, R.sup.3a, R.sup.1b, R.sup.2b, and R.sup.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.sup.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 ##STR00403## wherein R.sup.1a is a halogen atom, a lower alkyl group, or a lower alkoxy group, and R.sup.2a and R.sup.3a are hydrogen atoms; R.sup.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.sub.2. 4. The compound, or a pharmaceutically acceptable salt thereof according to claim 3, wherein R.sup.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: ##STR00404## wherein R.sup.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-(.beta.-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethy- lyl]benzene; 1-(.beta.-D-glucopyranosyl)-4-chloro-3-[5-(3-cyanophenyl)-2-thienylmethyl- ]benzene; 1-(.beta.-D-glucopyranosyl)-4-chloro-3-[(5-(4-cyanophenyl)-2-thi- enylmethyl]benzene; 1-(.beta.-D-glucopyranosyl)-4-methyl-3-[5-(6-fluoro-2-pyridyl)-2-thienylm- ethyl]benzene; 1-(.beta.-D-glucopyranosyl)-4-chloro-3-[5-(6-fluoro-2-pyridyl)-2-thienylm- ethyl]benzene; 1-(.beta.-D-glucopyranosyl)-4-methyl-3-[5-(3-difluoromethyl-phenyl)-2-thi- enylmethyl]benzene; 1-(.beta.-D-glucopyranosyl)-4-methyl-3-[5-(3-cyanophenyl)-2-thienylmethyl- ]benzene; 1-(.beta.-D-glucopyranosyl)-4-methyl-3-[5-(4-cyanophenyl)-2-thie- nylmethyl]benzene; and 1-(.beta.-D-glucopyranosyl)-4-chloro-3-[5-(6-fluoro-3-pyridyl)-2-thienylm- ethyl]benzene; or a pharmaceutically acceptable salt thereof. 10. 1-(.beta.-D-glucopyranosyl)-4-methyl-3-[5-(3-cyano-phenyl)-2-thienylm- ethyl]benzene, or a pharmaceutically acceptable salt thereof. 11. 1-(.beta.-D-glucopyranosyl)-4-methyl-3-[5-(4-cyano-phenyl)-2-thienylm- ethyl]benzene, or a pharmaceutically acceptable salt thereof. 12. 1-(.beta.-D-glucopyranosyl)-4-methyl-3-[5-(4-fluoro-phenyl)-2-thienyl- methyl]benzene, or a pharmaceutically acceptable salt thereof. 13. 1-(.beta.-D-glucopyranosyl)-4-chloro-3-[5-(3-cyano-phenyl)-2-thienylm- ethyl]benzene, or a pharmaceutically acceptable salt thereof. 14. 1-(.beta.-D-glucopyranosyl)-4-methyl-3-[5-(6-fluoro-2-pyridyl)-2-thie- nylmethyl]benzene, or a pharmaceutically acceptable salt thereof. 15. 1-(.beta.-D-glucopyranosyl)-4-chloro-3-[5-(6-fluoro-2-pyridyl)-2-thie- nylmethyl]benzene, or a pharmaceutically acceptable salt thereof. 16. 1-(.beta.-D-glucopyranosyl)-4-chloro-3-[5-(6-fluoro-3-pyridyl)-2-thie- nylmethyl]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: ##STR00405## wherein Ring A, Ring B, X and Y are as defined in claim 1, which comprises deprotecting a compound of formula II: ##STR00406## wherein Ring A, Ring B and Y are defined in claim 1 R.sup.11a is a hydrogen atom or a protecting group for a hydroxy group and R.sup.11b, R.sup.11c and R.sup.11d are each independently a protecting group for a hydroxy group. 19. A process for preparing a compound of formula I-a: ##STR00407## wherein Ring A, Ring B and Y are as defined in claim 1, which comprises reducing a compound of formula III: ##STR00408## wherein Ring A, Ring B and Y are as defined in claim 1, and R.sup.12 is a lower alkyl group. 20. A compound having the following structure: ##STR00409## 21. A pharmaceutical composition which comprises the compound of claim 20 and a pharmaceutically acceptable carrier or diluent. 22. 1-(.beta.-D-glucopyranosyl)-4-chloro-3-[5-(4-cyanophenyl)-2-thienylme- thyl]benzene or a pharmaceutically acceptable salt thereof. 23. 1-(.beta.-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 ##STR00410## wherein R.sup.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.sup.2a and R.sup.3a are hydrogen. 25. The compound, or a pharmaceutically acceptable salt thereof according to claim 24, wherein R.sup.1a is a halogen atom or an alkyl group, and R.sup.2a and R.sup.3a are hydrogen. 26. The compound, or a pharmaceutically acceptable salt thereof according to claim 1, wherein Ring A is ##STR00411## wherein R.sup.1b, R.sup.2b, and R.sup.3b are as defined in claim 1.