Crystalline glycopyrrolate tosylate

• US 8,859,610 B2
• Filed: 09/11/2013
• Issued: 10/14/2014
• Est. Priority Date: 02/28/2013
• Status: Active Grant

• Current Assignee: Journey Medical Corp. (Fortress Biotech, Inc.)
• Original Assignee: Dermira, Inc. (Eli Lilly and Company)
• Inventors: Statler, John Allan, Shaw, Anthony Adrian, Imbert, Delphine Caroline, Nelson, Jennifer Leigh, Andres, Patricia, McQueen, Lisa Lynn, Boerrigter, Stephan Xander Mattheus
• Primary Examiner(s): BARKER, MICHAEL P
• Application Number:
  US14/024,484
• Publication Number:
  US 20140242122A1
• Time in Patent Office: 398 Days
• Field of Search: 548/541, 514/424
• US Class Current: 514/424
• CPC Class Codes: C07C 309/30 of six-membered aromatic rings substituted by alkyl groups
• CPC Class Codes: C07D 207/12 Oxygen or sulfur atoms

Abstract

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.

Claims

1. An absorbant pad comprising a pharmaceutically acceptable solution comprising a racemic mixture of (R)-3-((S)-2-cyclopentyl-2-hydroxy-2-phenylacetoxy)-1,1-dimethylpyrrolidinium 4-methylbenzenesulfonate and (S)-3-((R)-2-cyclopentyl-2-hydroxy-2-phenylacetoxy)-1,1-dimethylpyrrolidinium 4-methylbenzenesulfonate or a solvate thereof and one or more pharmaceutically acceptable additives.

15. The solution of claim 1, wherein one pharmaceutically acceptable additive is ethanol.

2. A pharmaceutically acceptable solution comprising a racemic mixture of (R)-3-((S)-2-cyclopentyl-2-hydroxy-2-phenylacetoxy)-1,1-dimethylpyrrolidinium 4-methylbenzenesulfonate and (S)-3-((R)-2-cyclopentyl-2-hydroxy-2-phenylacetoxy)-1,1-dimethylpyrrolidinium 4-methylbenzenesulfonate or a solvate thereof and one or more pharmaceutically acceptable additives for topical administration.

16. The solution of claim 2, wherein one pharmaceutically acceptable additive is ethanol.

3. A method of treating hyperhidrosis comprising topically administering a therapeutically effective amount of a pharmaceutically acceptable solution of a racemic mixture of (R)-3-((S)-2-cyclopentyl-2-hydroxy-2-phenylacetoxy)-1,1-dimethylpyrrolidinium 4-methylbenzenesulfonate and (S)-3-((R)-2-cyclopentyl-2-hydroxy-2-phenylacetoxy)-1,1-dimethylpyrrolidinium 4-methylbenzenesulfonate or solvate thereof to the skin of a mammal.

4. The method of claim 3, wherein said mammal is human.

5. The method of claim 4, wherein said solution is applied to the axilla.

6. The method of claim 4, wherein said solution is applied to the hands.

7. The method of claim 4, wherein said solution is applied to the feet.

8. The method of claim 4, wherein said solution is applied to the groin, face, back, or abdomen.

9. The method of claim 3, where the administration is with an absorbent pad comprising an absorbed pharmaceutically acceptable solution of a racemic mixture of (R)-3-((S)-2-cyclopentyl-2-hydroxy-2-phenylacetoxy)-1,1-dimethylpyrrolidinium 4-methylbenzenesulfonate and (S)-3-((R)-2-cyclopentyl-2-hydroxy-2-phenylacetoxy)-1,1-dimethylpyrrolidinium 4-methylbenzenesulfonate.

10. The method of claim 4, where the administration is with an absorbent pad comprising an absorbed pharmaceutically acceptable solution of a racemic mixture of (R)-3-((S)-2-cyclopentyl-2-hydroxy-2-phenylacetoxy)-1,1-dimethylpyrrolidinium 4-methylbenzenesulfonate and (S)-3-((R)-2-cyclopentyl-2-hydroxy-2-phenylacetoxy)-1,1-dimethylpyrrolidinium 4-methylbenzenesulfonate.

11. The method of claim 5, where the administration is with an absorbent pad comprising an absorbed pharmaceutically acceptable solution of a racemic mixture of (R)-3-((S)-2-cyclopentyl-2-hydroxy-2-phenylacetoxy)-1,1-dimethylpyrrolidinium 4-methylbenzenesulfonate and (S)-3-((R)-2-cyclopentyl-2-hydroxy-2-phenylacetoxy)-1,1-dimethylpyrrolidinium 4-methylbenzenesulfonate.

12. The method of claim 6, wherein the administration is with an absorbent pad comprising an absorbed pharmaceutically acceptable solution of a racemic mixture of (R)-3-((S)-2-cyclopentyl-2-hydroxy-2-phenylacetoxy)-1,1-dimethylpyrrolidinium 4-methylbenzenesulfonate and (S)-3-((R)-2-cyclopentyl-2-hydroxy-2-phenylacetoxy)-1,1-dimethylpyrrolidinium 4-methylbenzenesulfonate.

13. The method of claim 7, wherein the administration is with an absorbent pad comprising an absorbed pharmaceutically acceptable solution of a racemic mixture of (R)-3-((S)-2-cyclopentyl-2-hydroxy-2-phenylacetoxy)-1,1-dimethylpyrrolidinium 4-methylbenzenesulfonate and (S)-3-((R)-2-cyclopentyl-2-hydroxy-2-phenylacetoxy)-1,1-dimethylpyrrolidinium 4-methylbenzenesulfonate.

14. The method of claim 8, wherein the administration is with an absorbent pad comprising an absorbed pharmaceutically acceptable solution of a racemic mixture of (R)-3-((S)-2-cyclopentyl-2-hydroxy-2-phenylacetoxy)-1,1-dimethylpyrrolidinium 4-methylbenzenesulfonate and (S)-3-((R)-2-cyclopentyl-2-hydroxy-2-phenylacetoxy)-1,1-dimethylpyrrolidinium 4-methylbenzenesulfonate.

17. The solution of claim 3, wherein one pharmaceutically acceptable additive is ethanol.

18. The solution of claim 4, wherein one pharmaceutically acceptable additive is ethanol.

19. The solution of claim 5, wherein one pharmaceutically acceptable additive is ethanol.

20. The solution of claim 6, wherein one pharmaceutically acceptable additive is ethanol.

21. The solution of claim 7, wherein one pharmaceutically acceptable additive is ethanol.

22. The solution of claim 8, wherein one pharmaceutically acceptable additive is ethanol.

23. The solution of claim 9, wherein one pharmaceutically acceptable additive is ethanol.

24. The solution of claim 10, wherein one pharmaceutically acceptable additive is ethanol.

25. The solution of claim 11, wherein one pharmaceutically acceptable additive is ethanol.

26. The solution of claim 12, wherein one pharmaceutically acceptable additive is ethanol.

27. The solution of claim 13, wherein one pharmaceutically acceptable additive is ethanol.

28. The solution of claim 14, wherein one pharmaceutically acceptable additive is ethanol.