# US 10,307,485 B2 · Pharmaceutical composition containing sympathomimetic amine salt and co-distillable additive > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,307,485 B2 - Document ID: US10307485B2 - Status: Granted - Kind: B2 - Application number: 15/609,723 - Filed: 2017-05-31 - Published: 2017-09-14 - Granted: 2019-06-04 - Earliest claimed: 2006-04-12 - Assignees: Wyeth - Applicants: Wyeth LLC - Inventors: David Hugh Giamalva; Gary Bruce Anderson - Web page: https://patentgrep.com/patent/US10307485B2 ## CPC - A61K 47/18: Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids - A61K 9/2013: {Organic compounds, e.g. phospholipids, fats} - A61K 31/137: Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine {or methadone} - A61K 31/192: having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid {(cannabinoids A61K31/658)} - A61K 31/205: Amine addition salts of organic acids; Inner quaternary ammonium salts, e.g. betaine, carnitine - A61K 31/473: ortho- or peri-condensed with carbocyclic ring systems, e.g. acridines, phenanthridines - A61K 31/485: Morphinan derivatives, e.g. morphine, codeine - A61K 31/616: by carboxylic acids, e.g. acetylsalicylic acid - A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca - A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D) ## Abstract A pharmaceutical composition is provided which contains a water soluble acid salt of a sympathomimetic amine, e.g., pseudoephedrine, and an additive, e.g., a volatile amine or other odorant, that is co-distillable, e.g., by steam distillation, with the sympathomimetic amine and/or its derivatives, e.g., its free base. ## Claims ### Claim 1 A pharmaceutical composition comprising a mixture which contains: i) a water soluble acid salt of a sympathomimetic amine, and ii) an additive that is co-distillable with the sympathomimetic amine as a free base, hydrochloride salt, or sulfate salt, wherein the additive is an odorant or a mixture of two or more odorants in an amount from about 0.1 to 1 part total additive per 100 parts of the sympathomimetic amine as a free base, hydrochloride salt, or sulfate salt, wherein the odorant or the mixture of two or more odorants selected from the group consisting of camphor, triethyl citrate, methyl anthranil, isoamyl acetate, geranyl acetate, linalool, alpha ionone, ortho-nitroacetophenone, and ortho-aminoacetophenone. ### Claim 2 (depends on 1) The pharmaceutical composition of claim 1 wherein said additive is co-distillable with the free base of said sympathomimetic amine. ### Claim 3 (depends on 1) The pharmaceutical composition of claim 1 wherein said additive is co-steam distillable with said sympathomimetic amine as a free base, hydrochloride salt, or sulfate salt. ### Claim 4 (depends on 3) The pharmaceutical composition of claim 3 wherein said additive is co-steam distillable with the free base of said sympathomimetic amine. ### Claim 5 (depends on 3) The pharmaceutical composition of claim 3 wherein said additive is co-steam distillable with the free base of said sympathomimetic amine as a free base, hydrochloride salt, or sulfate salt and is substantially unextractable from said sympathomimetic amine as a free base, hydrochloride salt, or sulfate salt. ### Claim 6 (depends on 3) The pharmaceutical composition of claim 3 wherein said additive is substantially unextractable by methanol extraction, n-hexane extraction, or acid/base extraction. ### Claim 7 (depends on 1) The pharmaceutical composition of claim 1 wherein the additive exhibits a vapor pressure at 100° C. which ranges from about 0.1 to about 10 times that of the sympathomimetic amine. ### Claim 8 (depends on 1) The pharmaceutical composition of claim 1 wherein the sympathomimetic amine is selected from the group consisting of ephedrine, phenylpropanolamine, and pseudoephedrine. ### Claim 9 (depends on 1) The pharmaceutical composition of claim 1 wherein said additive is an odorant. ### Claim 10 (depends on 9) The pharmaceutical composition of claim 9 wherein said odorant is co-distillable with said sympathomimetic amine as a free base, hydrochloride salt, or sulfate salt. ### Claim 11 (depends on 10) The pharmaceutical composition of claim 10 wherein said odorant is co-steam distillable with said sympathomimetic amine as a free base, hydrochloride salt, or sulfate salt. ### Claim 12 (depends on 1) The pharmaceutical composition of claim 1 wherein said additive is present in an amount sufficient to provide a product derived from distillation overhead wherein said product contains an odorant in an amount which is detectable by the mammalian sense of smell. ### Claim 13 (depends on 1) The pharmaceutical composition of claim 1 that comprises a further active ingredient selected from the group consisting of a fever reducer/pain reliever, an antihistamine, a cough suppressant/antitussive, an antihistamine/topical analgesic, and an expectorant. ### Claim 14 A method of reducing the isolatability of a water soluble acid salt of a sympathomimetic amine from a pharmaceutical composition containing said acid salt of a sympathomimetic amine, which comprises including within said pharmaceutical composition an odorant or a mixture of two or more odorants which is co-distillable with the sympathomimetic amine as a free base, hydrochloride salt, or sulfate salt, in an amount from about 0.1 to 1 part total additive per 100 parts of said amine as a free base, hydrochloride salt, or sulfate salt. ### Claim 15 (depends on 14) The method of claim 14 wherein said additive is co-steam distillable with the sympathomimetic amine as a free base, hydrochloride salt, or sulfate salt. ### Claim 16 (depends on 14) The method of claim 14 wherein said additive is substantially incapable of separation from said sympathomimetic amine as a free base, hydrochloride salt, or sulfate salt by a method or methods selected from the group consisting of solvent extraction, precipitation, simple distillation, and crystallization. ### Claim 17 (depends on 1) The pharmaceutical composition of claim 1 wherein said additive is a mixture of two or more odorants.