Glycopyrrolate salts
AssigneeJourney Medical Corporation
InventorsJohn Allan STATLER, Anthony Adrian SHAW, Delphine Caroline IMBERT, Jennifer Leigh NELSON, Patricia ANDRES, Lisa Lynn McQUEEN, Stephan Xander Mattheus BOERRIGTER, Jon Gordon SELBO, Mark Christopher ANDRES
Life of this patent
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Abstract
Salts of glycopyrrolate, including solid forms and formulations such as topicals thereof, are disclosed. Methods of making glycopyrrolate salts, including formulations such as topicals thereof, and methods of treating hyperhidrosis with salts of glycopyrrolate, and formulations such as topicals thereof, are disclosed.
Claims239
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.
A method of treating hyperhidrosis comprising topically administering a therapeutically effective amount of a pharmaceutically acceptable solution of glycopyrrolate tosylate or solvate thereof to the skin of a mammal.
A method of making threo glycopyrrolate tosylate comprising:
- a) treating racemic cyclopentylmandelic acid with racemic 1-methylpyrrolidin-3-ol and 1,1′ carbonyldiimidazole in a suitable solvent to form glycopyrrolate base;
- b) treating the glycopyrrolate base in a suitable solvent with a resolving acid to form a salt of threo glycopyrrolate;
- c) treating the salt of the threo glycopyrrolate salt with a suitable base in a suitable solvent to form a base of threo glycopyrrolate;
- and
- d) treating the base of threo glycopyrrolate with p-toulenesulfonic acid in a suitable solvent to form threo glycopyrrolate tosylate.
Crystalline glycopyrrolate tosylate.
Crystalline glycopyrrolate tosylate monohydrate.
Crystalline dehydrated Form D glycopyrrolate tosylate.
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.
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, wherein Y is an organic ion, 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.
Glycopyrrolate tosylate, co-crystals, polymorphs, hydrates and solvates thereof.
Solid glycopyrrolate tosylate.
X-ray amorphous glycopyrrolate tosylate.
A salt of glycopyrrolate selected from the benzoate, edisylate, oxalate, and hydrogen sulfate salts and hydrates and solvates thereof.
Crystalline glycopyrrolate acetate.
An absorbent pad containing an aqueous solution comprising glycopyrrolate tosylate absorbed onto the pad.
A gel comprising a pharmaceutically acceptable amount of glycopyrrolate tosylate.
An absorbent pad containing an aqueous glycopyrrolate solution comprising about 0.15% by weight anhydrous citric acid, about 0.06% sodium citrate dihydrate by weight, between about 57 to about 59.5% by weight of dehydrated ethanol, and between about 1% and about 6% by weight glycopyrrolate tosylate.
A process for making an absorbent pad containing an aqueous solution of glycopyrrolate tosylate absorbed onto the pad comprising treating solid glycopyrrolate tosylate in solution with water, one or more buffers and an alcohol, and mixing until dissolution;
- and wetting a pad with the glycopyrrolate tosylate solution so that a pharmaceutically acceptable amount of glycopyrrolate tosylate has been absorbed onto the pad.
A method of treating hyperhidrosis comprising topically administering a therapeutically effective amount of an aqueous glycopyrrolate tosylate solution from an absorbent pad to the skin of a mammal.
A solid dispersion comprising glycopyrrolate tosylate.
A method for treating primary axillary hyperhidrosis with glycopyrrolate tosylate or a solvate thereof comprising administering topically administering a therapeutically effective amount of an aqueous glycopyrrolate tosylate solution to the skin of a mammal in need thereof.
A method for treating palmar or plantar hyperhidrosis with glycopyrrolate tosylate or a solvate thereof comprising administering topically administering a therapeutically effective amount of an aqueous glycopyrrolate tosylate solution to the skin of a mammal in need thereof.
Glycopyrrolate tosylate.
A topical comprising threo glycopyrrolate tosylate.
A cream or ointment comprising a pharmaceutically acceptable amount of glycopyrrolate tosylate.
A process for making an aqueous formulation comprising threo glycopyrrolate tosylate comprising treating solid glycopyrrolate tosylate in solution with water, a buffer and an alcohol, and mixing until dissolution.
A process for making an aqueous formulation comprising glycopyrrolate tosylate comprising dissolving crystalline glycopyrrolate tosylate in solution comprising water.
Dependencies are inferred from the claim text.