Crystalline glycopyrrolate tosylate
View Patent ↗Salts of glycopyrrolate, including solid forms thereof are herein disclosed. Methods of making glycopyrrolate salts and methods of treating hyperhidrosis with salts of glycopyrrolate are disclosed.
1. Form D crystalline glycopyrrolate tosylate monohydrate characterized by an x-ray powder diffraction pattern comprising one or more peaks at about 6.9°2θ and about 12.6°2θ, prepared by treating glycopyrrolate bromide with a metal salt in a suitable solvent to form a glycopyrrolate salt slurry; removing the solids in the slurry to form a solution; lyophilizing the solution to form a solid; dissolving the solid in a crystallization solvent; and removing the crystallization solvent to form Form D.
2. The crystalline glycopyrrolate tosylate monohydrate of claim 1 , further characterized by an x-ray powder diffraction pattern comprising one or more peaks at about 10.3, 13.7, 14.9, 15.3, 15.7, 16.4, 17.7, or 18.2 °2θ.
3. The crystalline glycopyrrolate tosylate monohydrate of claim 1 , wherein the metal salt is a silver salt
4. The crystalline glycopyrrolate tosylate monohydrate of claim 2 , wherein the metal salt is a silver salt.
5. The crystalline glycopyrrolate tosylate monohydrate of claim 4 , wherein the suitable solvent is an alcohol.
6. The crystalline glycopyrrolate tosylate monohydrate of claim 5 , wherein the alcohol is isopropanol.
7. The crystalline glycopyrrolate tosylate monohydrate of claim 2 , wherein the crystallization solvent comprises acetonitrile and water.
8. The crystalline glycopyrrolate tosylate monohydrate of claim 3 , wherein the crystallization solvent comprises acetonitrile and water.
9. The crystalline glycopyrrolate tosylate monohydrate of claim 5 , wherein the crystallization solvent comprises acetonitrile and water.
10. The crystalline glycopyrrolate tosylate monohydrate of claim 6 , wherein the crystallization solvent comprises acetonitrile and water.
11. The crystalline glycopyrrolate tosylate monohydrate of claim 10 , wherein the crystallization solvent is removed by lowering the temperature of the solid in the crystallization solvent and decanting the solvent.
12. The crystalline glycopyrrolate tosylate monohydrate of claim 11 , further comprising the addition of an anti-solvent.
13. The crystalline glycopyrrolate tosylate monohydrate of claim 12 , wherein the antisolvent is toluene.
14. Form D crystalline glycopyrrolate tosylate monohydrate characterized by an x-ray powder diffraction pattern comprising one or more peaks at about 6.9°2θ and about 12.6°2θ , prepared by treating glycopyrrolate-Y and p-toluenesulfonic acid in a suitable solvent; removing the solvent to form a solid; re-dissolving the solid in a crystallization solvent to form a solution; and removing the crystallization solvent to form Form D glycopyrrolate tosylate.
15. The crystalline glycopyrrolate tosylate monohydrate of claim 14 , wherein Y is an organic ion.
16. The crystalline glycopyrrolate tosylate monohydrate of claim 15 , wherein Y is acetate.
17. The crystalline glycopyrrolate tosylate monohydrate of claim 16 , wherein the suitable solvent is isopropanol and the suitable solvent comprises acetonitrile and water.
18. The crystalline glycopyrrolate tosylate monohydrate of claim 17 , wherein the crystallization solvent is removed by evaporation.