Crystalline complex of 1-cyano-2-(4-cyclopropyl-benzyl)-4-(ss-d-glucopyranos-1-yl)-benzene, methods for its preparation and the use thereof for preparing medicaments

1. Crystalline complex between 1-cyano-2-(4-cyclopropyl-benzyl)-4-(β-D-glucopyranos-1-yl)-benzene and one or more natural amino acids.

2. Crystalline complex according to claim 1 , wherein the natural amino acid is proline.

3. Crystalline complex according to claim 2 , wherein it is a complex of 1-cyano-2-(4-cyclopropyl-benzyl)-4-(β-D-glucopyranos-1-yl)-benzene and proline with a molar ratio in the range from about 2 : 1 to about 1:3.

4. Crystalline complex according to claim 2 wherein the content of water is in the range from about 0 to 3 mol per mol of 1-cyano-2-(4-cyclopropyl-benzyl)-4-(β-D-glucopyranos-1-yl)-benzene.

5. Crystalline complex according to claim 2 , wherein the crystalline complex is characterized by an X-ray powder diffraction pattern made using CuK α1 radiation that comprises peaks at 20.28, 21.14 and 21.64 degrees 2Θ(±0.1 degrees 2Θ).

6. Crystalline complex according to claim 5 , wherein the X-ray powder diffraction pattern made using CuK α1 radiation further comprises peaks at 4.99 and 23.23degrees 2Θ(±0.1 degrees 2Θ).

7. Crystalline complex according to claim 5 , wherein the X-ray powder diffraction pattern made using CuK α1 radiation further comprises peaks at 17.61, 17.77 and 27.66 degrees 2Θ(±0.1 degrees 2Θ).

8. Crystalline complex according to claim 1 wherein at least 50% of said complex is present as a crystalline complex in accordance with claim 5 .

9. A pharmaceutical composition comprising one or more crystalline complexes in accordance with claim 1 .

10. A medicament comprising the crystalline complex of claim 1 .

11. A method for treatment of type 2 diabetes mellitus the crystalline complex of claim 1 .

12. A method for inhibition of sodium dependent glucose cotransporter SGLT2 in a subject, the method comprising administering to the subject the crystalline complex of claim 1 .

13. A method for making the crystalline complex in accordance with claim 1 , said method comprising the following steps:

a) preparing a solution of 1-cyano-2-(4-cyclopropyl-benzyl)-4-(β-D-glucopyranos-1-yl)-benzene and the one or more natural amino acids in a solvent or a mixture of solvents;

b) storing the solution to precipitate the crystalline complex out of solution;

c) removing the precipitate from the solution; and

d) drying the precipitate optionally until any excess of said solvent or mixture of solvents has been removed.