Crystalline glycopyrrolate tosylate

• US 8,558,008 B2
• Filed: 02/28/2013
• Issued: 10/15/2013
• 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: Imbert, Delphine Caroline, Andres, Patricia, McQueen, Lisa Lynn, Statler, John Allan, Shaw, Anthony Adrian, Nelson, Jennifer Leigh, Boerrigter, Stephan Xander Mattheus
• Primary Examiner(s): SHTERENGARTS, SAMANTHA L
• Application Number:
  US13/781,390
• Publication Number:
  US 20130211101A1
• Time in Patent Office: 229 Days
• Field of Search: 548/556
• US Class Current: 548/556
• 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. Crystalline glycopyrrolate tosylate.

11. Form C crystalline glycopyrrolate tosylate of claim 1.

12. Form C crystalline glycopyrrolate tosylate of claim 11 characterized by x-ray powder diffraction pattern comprising a peak at about 5.5 °

2θ

.

13. Form C crystalline glycopyrrolate tosylate of claim 11 characterized by an x-ray powder diffraction pattern comprising a peak at about 11.0 °

2θ

.

14. Form C crystalline glycopyrrolate tosylate of claim 11 comprising an x-ray powder diffraction pattern comprising two or more peaks at about 5.5, 11.0, 11.8, 13.9, 14.9, 17.8, 19.6, 20.4, 21.6 or 22.1 °

2θ

.

15. Form C crystalline glycopyrrolate tosylate of claim 11 characterized by an infrared spectrum comprising one or more peaks at about 1733, 1236, 1211, 1198, 1186, 1177, 1120, 1032, 1008, or 682 cm⁻

1.

16. Form C crystalline glycopyrrolate tosylate of claim 11 characterized by (i) an x-ray powder diffraction pattern comprising two or more peaks at about 5.5, 11.0, 11.8, 13.9, 14.9, 17.8, 19.6, 20.4, 21.6, or 22.1 °

2θ

; and

(ii) an infrared spectrum comprising one or more peaks at about 1733, 1236, 1211, 1198, 1186, 1177, 1120, 1032, 1008, or 682 cm<sup>−

1</sup>.

17. Form C crystalline glycopyrrolate tosylate of claim 11 characterized by substantially the same x-ray powder diffraction pattern as FIG. 4.

18. Form C crystalline glycopyrrolate tosylate of claim 11 characterized by substantially the same infrared spectrum as FIG. 5.

2. Crystalline glycopyrrolate tosylate monohydrate.

3. Form D crystalline glycopyrrolate tosylate monohydrate of claim 2 characterized by an x-ray powder diffraction pattern comprising a peak at about 6.9 °

2θ

.

4. Form D crystalline glycopyrrolate tosylate monohydrate of claim 2 characterized by an x-ray powder diffraction pattern comprising a peak at about 12.6 °

2θ

.

5. Form D crystalline glycopyrrolate tosylate monohydrate of claim 2 characterized by an x-ray powder diffraction pattern comprising one peak at 6.9 °

2θ

or 12.6 °

2θ and

further 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

.

6. Form D crystalline glycopyrrolate tosylate monohydrate of claim 2 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

.

7. Form D crystalline glycopyrrolate tosylate monohydrate of claim 2 characterized by an infrared spectrum comprising one or more peaks at about 1734, 1196, 1125, 1036, 1013, or 682 cm⁻

1.

8. Form D crystalline glycopyrrolate tosylate monohydrate of claim 2 characterized by (i) an x-ray powder diffraction pattern comprising one or more peaks at about 6.9, 10.3, 12.6, 13.7, 14.9, 15.3, 15.7, 16.4, 17.7, or 18.2 °

2θ

; and

(ii) an infrared spectrum comprising one or more peaks at about 1734, 1196, 1125, 1036, 1013, or 682 cm<sup>−

1</sup>.

9. Form D crystalline glycopyrrolate tosylate monohydrate of claim 2 characterized by substantially the same x-ray powder diffraction pattern as in FIG. 2.

10. Form D crystalline glycopyrrolate tosylate monohydrate of claim 2 characterized by substantially the same infrared spectrum as in FIG. 3.

19. Crystalline dehydrated Form D glycopyrrolate tosylate.

20. The dehydrated Form D glycopyrrolate tosylate of claim 19 wherein the x-ray powder diffraction is substantially the same as that of FIG. 8.