IP Library › Granted Patent US 8,283,326
Granted Patent B2
US 8,283,326 · App. 12/446,003 · Granted Oct 9, 2012

Crystalline form of 4-(beta-D-glucopyranos-1-yl)-1-methyl-2-[4-((S)-tetrahydrofuran-3-yloxy)-benzyl]-benzene, a method for its preparation and the use thereof for preparing medicaments

Assignee: Boehringer Ingelheim International GmbH
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Quick Facts
Patent No.
US 8,283,326
App. No.
12/446,003
Granted
Oct 9, 2012
Kind
B2
Abstract

The invention relates to a crystalline form of 4-(β-D-glucopyranos-1-yl)-1-methyl-2-[4-((S)-tetrahydrofuran-3-yloxy)-benzyl]-benzene, to a method for the preparation thereof, as well as to the use thereof for preparing medicaments.

Claims (22)

1. A crystalline form of 4-(β-D-glucopyranos-1-yl)-1-methyl-2-[4-((S)-tetrahydrofuran-3-yloxy)-benzyl]-benzene having an X-ray powder diffraction pattern that comprises peaks at 18.62, 19.27 and 20.35 degrees 2Θ (±0.05 degrees 2Θ), wherein said X-ray powder diffraction pattern is made using CuKα1 radiation.

2. The crystalline form according to claim 1 , wherein the X-ray powder diffraction pattern further comprises peaks at 9.83, 18.96 and 20.18 degrees 2Θ (±0.05 degrees 2Θ), wherein said X-ray powder diffraction pattern is made using CuKα1 radiation.

3. 4-(β-D-glucopyranos-1-yl)-1-methyl-2-[4-((S)-tetrahydrofuran-3-yloxy)-benzyl]-benzene wherein at least 50% of said substance is present in the form of the crystalline form in accordance with claim 1 .

4. A pharmaceutical composition comprising the crystalline form in accordance with claim 1 .

5. Method for the treatment of diseases or conditions which can be influenced by inhibiting the sodium-dependent glucose cotransporter SGLT comprising administering to a patient a crystalline form in accordance to claim 1 .

6. Method for the treatment of metabolic disorders, in particular of a metabolic disorder selected from the group consisting of type 1 and type 2 diabetes mellitus, complications of diabetes, metabolic acidosis or ketosis, reactive hypoglycaemia, hyperinsulinaemia, glucose metabolic disorder, insulin resistance, metabolic syndrome, dyslipidaemias of different origins, atherosclerosis and related diseases, obesity, high blood pressure, chronic heart failure, oedema and hyperuricaemia comprising administering to a patient a crystalline form in accordance to claim 1 .

7. Method for inhibiting the sodium-dependent glucose cotransporter SGLT2 comprising administering to a patient a crystalline form in accordance to claim 1 .

8. Method for treating the degeneration of pancreatic beta cells and/or for improving and/or restoring the functionality of pancreatic beta cells SGLT2 comprising administering to a patient a crystalline form in accordance to claim 1 .

9. Method for preventing, slowing, delaying or treating diseases or conditions attributed to an abnormal accumulation of liver fat in a patient in need thereof SGLT2 comprising administering to a patient a crystalline form in accordance to claim 1 .

10. A method for making the crystalline form in accordance with claim 2 , said method comprising the following steps:

(a) dissolving 4-(β-D-glucopyranos-1-yl)-1-methyl-2-[4-(S)-tetrahydrofuran-3-yloxy)-benzyl]-benzene in a solvent or a mixture of solvents to form a solution;

(b) storing the solution to precipitate the crystalline form in accordance with claim 1 out of solution and thus to yield a suspension;

(c) isolating the precipitate from the suspension; and

(d) drying the precipitate to remove an excess of said solvent or mixture of solvents.

11. 4-(β-D-glucopyranos-1-yl)-1-methyl-2- [4((S)-tetrahydrofuran-3-yloxy)-benzyl]-benzene wherein at least 50% of said substance is present in the form of the crystalline form in accordance with claim 3 .

12. A pharmaceutical composition comprising the crystalline form in accordance with claim 3 .

13. Method for the treatment of diseases or conditions which can be influenced by inhibiting the sodium-dependent glucose cotransporter SGLT comprising administering to a patient a crystalline form in accordance to claim 3 .

14. Method for the treatment of metabolic disorders selected from the group consisting of type 1 and type 2 diabetes mellitus, complications of diabetes, metabolic acidosis or ketosis, reactive hypoglycaemia, hyperinsulinaemia, glucose metabolic disorder, insulin resistance, metabolic syndrome, dyslipidaemias of different origins, atherosclerosis and related diseases, obesity, high blood pressure, chronic heart failure, oedema and hyperuricaemia comprising administering to a patient a crystalline form in accordance to claim 3 .

15. Method for inhibiting the sodium-dependent glucose cotransporter SGLT2 comprising administering to a patient a crystalline form in accordance to claim 3 .

16. Method for treating the degeneration of pancreatic beta cells and/or for improving and/or restoring the functionality of pancreatic beta cells SGLT2comprising administering to a patient a crystalline form in accordance to claim 3 .

17. Method for slowing, delaying or treating diseases or conditions attributed to an abnormal accumulation of liver fat in a patient in need thereof SGLT2comprising administering to a patient a crystalline form in accordance to claim 3 .

18. A method for making the crystalline form in accordance with claim 3 , said method comprising the following steps: (a) dissolving 4-(β-D-glucopyranos-1-yl)-1-methyl-2-[4-((S)-tetrahydrofuran-3-yloxy)- benzyl]-benzene in a solvent or a mixture of solvents to form a solution; (b) storing the solution to precipitate the crystalline form in accordance with claim 2 out of solution and thus to yield a suspension; (c) isolating the precipitate from the suspension; and (d) drying the precipitate to remove an excess of said solvent or mixture of solvents.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 9, 2009
From: ECKHARDT, MATTHIAS; HIMMELSBACH, FRANK; BUTZ, TANJA M.; MARTIN, HANS-JUERGEN
To: BOEHRINGER INGELHEIM INTERNATIONAL GMBH
Reel/Frame 022935/0860 →
Priority Claims (1)
EP 06123068 · Oct 27, 2006 · regional
Continuity (1)
Related Publication 20100317847A1 · Dec 16, 2010