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Last Updated: November 28, 2020

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Claims for Patent: 7,579,449

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Summary for Patent: 7,579,449
Title:Glucopyranosyl-substituted phenyl derivatives, medicaments containing such compounds, their use and process for their manufacture
Abstract: Glucopyranosyl-substituted benzene derivatives of general formula I ##STR00001## where the groups R.sup.1 to R.sup.6 as well as R.sup.7a, R.sup.7b, R.sup.7c are defined herein and the tautomers, the stereoisomers thereof, the mixtures thereof and the salts thereof. The compounds according to the invention are suitable for the treatment of metabolic disorders.
Inventor(s): Eckhardt; Matthias (Biberach, DE), Eickelmann; Peter (Mittelbiberach, DE), Himmelsbach; Frank (Mittelbiberach, DE), Barsoumian; Edward Leon (Toyonaka, JP), Thomas; Leo (Biberach, DE)
Assignee: Boehringer Ingelheim International GmbH (Ingelheim, DE)
Application Number:11/080,150
Patent Litigation and PTAB cases: See patent lawsuits and PTAB cases for patent 7,579,449
Patent Claims: 1. Glucopyranosyl-substituted benzene derivatives of general formula I.2c ##STR00117## wherein R.sup.1 is selected from hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, isopropyl, ethynyl, hydroxy, methoxy, ethoxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, and R.sup.2 is hydrogen, fluorine, hydroxy, methoxy, ethoxy or methyl, and R.sup.3 is selected from trimethylsilylethyl, ethynyl, 2-hydroxyprop-2-ylethynyl, 2-methoxyprop-2-ylethynyl, 3-hydroxy-1-propyn-1-yl, 3-methoxy-1-propyn-1-yl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuran-3-yloxy, tetrahydropyran-4-yloxy, piperidin-4-yloxy, N-methylpiperidin-4-yloxy and N-acetylpiperidin-4-yloxy, and R.sup.4, R.sup.5 independently of one another is hydrogen or fluorine, and R.sup.6 is hydrogen, (C.sub.1-6-alkyl)carbonyl or (C.sub.1-6-alkyl)oxycarbonyl, and R.sup.7a, R.sup.7b and R.sup.7c are hydrogen, while, unless otherwise stated, the above-mentioned alkyl groups may be straight-chain or branched, the stereoisomers thereof, the mixtures thereof and the salts thereof.

2. Glucopyranosyl-substituted benzene derivatives according to claim 1, wherein R.sup.1 is methyl or chlorine.

3. Glucopyranosyl-substituted benzene derivatives according to claim 1, wherein R.sup.3 is ethynyl.

4. Glucopyranosyl-substituted benzene derivatives according to claim 1, wherein R.sup.3 is trimethylsilylethyl.

5. Glucopyranosyl-substituted benzene derivatives according to claim 1, wherein R.sup.3 is cyclobutyloxy.

6. Glucopyranosyl-substituted benzene derivatives according to claim 1, wherein R.sup.3 is cyclopentyloxy.

7. Glucopyranosyl-substituted benzene derivatives according to claim 1, wherein R.sup.3 is cyclohexyloxy.

8. Glucopyranosyl-substituted benzene derivatives according to claim 1, wherein R.sup.3 is tetrahydrofuran-3-yloxy.

9. Glucopyranosyl-substituted benzene derivatives according to claim 1, wherein R.sup.3 is tetrahydropyran-4-yloxy.

10. Glucopyranosyl-substituted benzene derivatives according to claim 1, wherein R.sup.2 is hydrogen or methyl.

11. Glucopyranosyl-substituted benzene derivatives according to claim 1, wherein R.sup.2 is hydrogen.

12. Glucopyranosyl-substituted benzene derivatives according to claim 1, wherein R.sup.4 and R.sup.5 are hydrogen.

13. Glucopyranosyl-substituted benzene derivatives according to claim 1, wherein R.sup.6 is hydrogen.

14. 1 -Chloro-2-(4-cyclopentyloxybenzyl)-4-(.beta.-D-glucopyranos- 1-yl)-benzene.

15. 1 -Chloro-4-(.beta.-D-glucopyranos-1-yl)-2-[4-((R)-tetrahydrofuran-3-- yloxy)-benzyl]-benzene.

16. 1 -Chloro-4-(.beta.-D-glucopyranos-1-yl)-2-[4-((S)-tetrahydrofuran-3-- yloxy)-benzyl]-benzene.

17. 1 -Chloro-4-(.beta.-D-glucopyranos-1-yl)-2-(4-cyclobutyloxy-benzyl)-b- enzene.

18. 1 -Chloro-4-(.beta.-D-glucopyranos-1-yl)-2-(4-cyclohexyloxy-benzyl)-b- enzene.

19. 1 -Chloro-4-(.beta.-D-glucopyranos-1-yl)-2-[4-(tetrahydropyran-4-ylox- y)-benzyl]-benzene.

20. 1 -Chloro-4-(.beta.-D-glucopyranos-1-yl)-2-[4-(1-acetyl-piperidin-4-y- loxy)-benzyl]-benzene.

21. 1-(.beta.-D-Glucopyranos-1-yl)-4-methyl-3-[4-(2-trimethylsilyl-ethyl)- -benzyl]-benzene.

22. 1-Chloro-4-(.beta.-D-glucopyranos-1-yl)-2-(4-ethynyl-benzyl)-benzene.

23. 1-Fluoro-4-(.beta.-D-glucopyranos-1-yl)-2-(4-ethynyl-benzyl)-benzene.

24. 1-(.beta.-D-Glucopyranos-1-yl)-3-(4-ethynyl-benzyl)-benzene.

25. 1-Methoxy-4-(.beta.-D-glucopyranos-1-yl)-2-(4-ethynyl-benzyl)-benzene- .

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