# US 9,006,461 B2 · Crystalline glycopyrrolate tosylate

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- Number: US 9,006,461 B2
- Document ID: US9006461B2
- Status: Granted
- Kind: B2
- Application number: 14/024,480
- Filed: 2013-09-11
- Published: 2014-08-28
- Granted: 2015-04-14
- Earliest claimed: 2013-02-28
- Assignees: Dermira, Inc.
- Applicants: Dermira, Inc.
- Inventors: John Allan Statler; Anthony Adrian Shaw; Delphine Caroline Imbert; Jennifer Leigh Nelson; Patricia Andres; Lisa Lynn McQueen; Stephan Xander Mattheus Boerrigter
- Web page: https://patentgrep.com/patent/US9006461B2

## CPC

- C07D 207/12: Oxygen or sulfur atoms
- C07C 309/30: of six-membered aromatic rings substituted by alkyl groups
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## 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

### Claim 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.

### Claim 2 (depends on 1)

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.

### Claim 3 (depends on 1)

The crystalline glycopyrrolate tosylate monohydrate of claim 1, wherein the metal salt is a silver salt

### Claim 4 (depends on 2)

The crystalline glycopyrrolate tosylate monohydrate of claim 2, wherein the metal salt is a silver salt.

### Claim 5 (depends on 4)

The crystalline glycopyrrolate tosylate monohydrate of claim 4, wherein the suitable solvent is an alcohol.

### Claim 6 (depends on 5)

The crystalline glycopyrrolate tosylate monohydrate of claim 5, wherein the alcohol is isopropanol.

### Claim 7 (depends on 2)

The crystalline glycopyrrolate tosylate monohydrate of claim 2, wherein the crystallization solvent comprises acetonitrile and water.

### Claim 8 (depends on 3)

The crystalline glycopyrrolate tosylate monohydrate of claim 3, wherein the crystallization solvent comprises acetonitrile and water.

### Claim 9 (depends on 5)

The crystalline glycopyrrolate tosylate monohydrate of claim 5, wherein the crystallization solvent comprises acetonitrile and water.

### Claim 10 (depends on 6)

The crystalline glycopyrrolate tosylate monohydrate of claim 6, wherein the crystallization solvent comprises acetonitrile and water.

### Claim 11 (depends on 10)

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.

### Claim 12 (depends on 11)

The crystalline glycopyrrolate tosylate monohydrate of claim 11, further comprising the addition of an anti-solvent.

### Claim 13 (depends on 12)

The crystalline glycopyrrolate tosylate monohydrate of claim 12, wherein the antisolvent is toluene.

### Claim 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.

### Claim 15 (depends on 14)

The crystalline glycopyrrolate tosylate monohydrate of claim 14, wherein Y is an organic ion.

### Claim 16 (depends on 15)

The crystalline glycopyrrolate tosylate monohydrate of claim 15, wherein Y is acetate.

### Claim 17 (depends on 16)

The crystalline glycopyrrolate tosylate monohydrate of claim 16, wherein the suitable solvent is isopropanol and the suitable solvent comprises acetonitrile and water.

### Claim 18 (depends on 17)

The crystalline glycopyrrolate tosylate monohydrate of claim 17, wherein the crystallization solvent is removed by evaporation.