Claims for Patent: 8,785,403

Summary for Patent: 8,785,403

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); or 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:	13/494,602
Patent Litigation and PTAB cases:	See patent lawsuits and PTAB cases for patent 8,785,403
Patent Claims:	1. A pharmaceutical composition comprising (i) 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, 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 heterocyclyl group is a thienyl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, pyrazolyl group, a thiazolyl 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; (ii) an antidiabetic agent selected from the group consisting of insulin, an insulin secretagogue, an insulin sensitizer, a biguanide compound, a sulfonylurea compound, an .alpha.-glucosidase inhibitor, a PPAR.gamma. agonist, a PPAR.alpha./.gamma. dual agonist, a dipeptidyl peptidase IV inhibitor, a mitiglinide compound, a nateglinide compound, a glucagon-like peptide-1, a PTP1B inhibitor, a glycogen phosphorylase inhibitor, a RXR modulator, and a glucose 6-phosphatase inhibitor; and (iii) a pharmaceutically acceptable carrier. 2. The pharmaceutical composition 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 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 a halogen atom, a cyano group, a lower alkyl group, or a lower alkoxy group. 3. The pharmaceutical composition 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, or a lower alkoxy group, and Y is --CH.sub.2--. 4. The pharmaceutical composition of claim 1, 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. The pharmaceutical composition according to claim 1, wherein the compound is 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, and 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, and a halo-lower alkoxy group; where the heterocyclyl group is a thienyl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, pyrazolyl group, a thiazolyl group, a quinolyl group, or a tetrazolyl group; or a pharmaceutically acceptable salt thereof. 6. The pharmaceutical composition 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 pharmaceutical composition according to claim 5, 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 pharmaceutical composition 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 pharmaceutical composition 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- l]benzene; 1-(.beta.-D-glucopyranosyl)-4-chloro-3-[5-(3-cyanophenyl)-2-thi- enylmethyl]benzene; 1-(.beta.-D-glucopyranosyl)-4-chloro-3-[5-(4-cyanophenyl)-2-thienylmethyl- ]benzene; 1-(.beta.-D-glucopyranosyl)-4-methyl-3-[5-(6-fluoro-2-pyridyl)-2- -thienylmethyl]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. The pharmaceutical composition according to claim 1, wherein the compound is 1-(.beta.-D-glucopyranosyl)-4-methyl-3-[5-(3-cyano-phenyl)-2-thienylmethy- l]benzene, or a pharmaceutically acceptable salt thereof. 11. The pharmaceutical composition according to claim 1, wherein the compound is 1-(.beta.-D-glucopyranosyl)-4-methyl-3-[5-(4-cyano-phenyl)-2-thienylmethy- l]benzene, or a pharmaceutically acceptable salt thereof. 12. The pharmaceutical composition according to claim 1, wherein the compound is 1-(.beta.-D-glucopyranosyl)-4-methyl-3-[5-(4-fluoro-phenyl)-2-thienylmeth- yl]benzene, or a pharmaceutically acceptable salt thereof. 13. The pharmaceutical composition according to claim 1, wherein the compound is 1-(.beta.-D-glucopyranosyl)-4-chloro-3-[5-(3-cyano-phenyl)-2-thienylmethy- l]benzene, or a pharmaceutically acceptable salt thereof. 14. The pharmaceutical composition according to claim 1, wherein the compound is 1-(.beta.-D-glucopyranosyl)-4-methyl-3-[5-(6-fluoro-2-pyridyl)-2-thienylm- ethyl]benzene, or a pharmaceutically acceptable salt thereof. 15. The pharmaceutical composition according to claim 1, wherein the compound is 1-(.beta.-D-glucopyranosyl)-4-chloro-3-[5-(6-fluoro-2-pyridyl)-2-thienylm- ethyl]benzene, or a pharmaceutically acceptable salt thereof. 16. The pharmaceutical composition according to claim 1, wherein the compound is 1-(.beta.-D-glucopyranosyl)-4-chloro-3-[5-(6-fluoro-3-pyridyl)-2-thienylm- ethyl]benzene, or a pharmaceutically acceptable salt thereof. 17. The pharmaceutical composition according to claim 1, wherein said antidiabetic agent is a biguanide compound. 18. The pharmaceutical composition according to claim 1, wherein said antidiabetic agent is a dipeptidyl peptidase IV inhibitor. 19. The pharmaceutical composition according to claim 1, wherein said antidiabetic agent is insulin. 20. The pharmaceutical composition pharmaceutical composition according to claim 1, wherein said antidiabetic agent is an insulin secretagogue. 21. The pharmaceutical composition according to claim 1, wherein said antidiabetic agent is a sulfonylurea compound. 22. The pharmaceutical composition according the claim 1, wherein said antidiabetic agent is an .alpha.-glucosidase inhibitor. 23. The pharmaceutical composition according to claim 1, wherein said antiabetic agent is a PPAR.gamma. agonist. 24. The pharmaceutical composition according to claim 1, wherein said antidiabetic agent is a PPAR.alpha./.gamma. dual agonist. 25. A pharmaceutical composition comprising (i) a compound having the following structure or a pharmaceutically acceptable salt thereof: ##STR00405## (ii) an antidiabetic agent selected from the group consisting of insulin, an insulin secretagogue, an insulin sensitizer, a biguanide compound, a sulfonylurea compound, an .alpha.-glucosidase inhibitor, a PPAR.gamma. agonist, a PPAR.alpha./.gamma. dual agonist, a dipeptidyl peptidase IV inhibitor, a mitiglinide compound, a nateglinide compound, a glucagon-like peptide-1, a PTP1B inhibitor, a glycogen phosphorylase inhibitor, an RXR modulator, and a glucose 6-phosphatase inhibitor; and (iii) a pharmaceutically acceptable carrier. 26. The pharmaceutical composition of claim 25, wherein the antidiabetic agent is a biguanide compound.