High purity nitric oxide releasing compounds and methods of preparing same
AssigneeKNOW Bio, LLC
InventorsMona Jasmine R. Ahonen, John Kelly Simons, Thomas Goldthwaite Coleman
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Abstract
Provided herein is a method of manufacturing a high purity nitric oxide releasing compound product preparation. Also described herein is a high purity nitric oxide releasing compound product preparation prepared according to the manufacturing method. A high purity nitric oxide releasing compound product, having a purity of at least 97 area % as measured by high pressure liquid chromatography and a residual solvent level of less than 1.5% is further described herein.
Claims34
A method of manufacturing a high purity nitric oxide releasing compound product preparation, comprising:
- preparing in a vessel a reaction mixture comprising a hydroxide or a hydroxide donor and one or more reaction mixture solvents;
- introducing nitric oxide into the vessel under an inert atmosphere to obtain a suspension comprising a nitric oxide releasing compound;
- filtering the suspension to obtain a nitric oxide releasing compound solid;
- dissolving the nitric oxide releasing compound solid in an aqueous solution to form a dissolved nitric oxide releasing compound solution;
- recrystallizing the nitric oxide releasing compound solid from the dissolved nitric oxide releasing compound solution to form a recrystallized nitric oxide releasing compound product, wherein the recrystallizing comprises a step of adding methanol to the dissolved nitric oxide releasing compound solution;
- filtering the recrystallized nitric oxide releasing compound product and washing the filtered recrystallized nitric oxide releasing compound product with a mixture of washing solvents to form a washed nitric oxide releasing compound product, wherein the mixture of washing solvents comprises methanol and one or more additional alcohols;
- drying the washed nitric oxide releasing compound product to form a dried nitric oxide releasing compound product;
- and
- dissolving the dried nitric oxide releasing compound product in water to form the high purity nitric oxide releasing compound product preparation.
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A high purity nitric oxide releasing compound product, comprising:
- a compound having at least two diazeniumdiolate groups on one carbon atom, each having a charge and each with an associated pharmaceutically-acceptable cation to balance the charge on the diazeniumdiolate groups, which compound has a molecular weight below 500 g/mol, not including the associated pharmaceutically-acceptable cation,
- wherein the high purity nitric oxide releasing compound product has a purity of at least 97 area % as measured by high pressure liquid chromatography;
- and
- wherein the high purity nitric oxide releasing compound product has a residual solvent level of less than 1.5% w/w.
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Dependencies are inferred from the claim text.