# US 11,433,041 B2 · Palatable compositions including sodium phenylbutyrate and uses thereof > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,433,041 B2 - Document ID: US11433041B2 - Status: Granted - Kind: B2 - Application number: 16/746,186 - Filed: 2020-01-17 - Published: 2020-08-20 - Granted: 2022-09-06 - Earliest claimed: 2016-03-15 - Assignees: Acer Therapeutics Inc. - Applicants: Acer Therapeutics[,] Inc. - Inventors: Leah E. Appel; Joshua R. Shockey; D. Christopher Schelling - Web page: https://patentgrep.com/patent/US11433041B2 ## CPC - A61K 31/192: having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid {(cannabinoids A61K31/658)} - A61K 9/5078: {with drug-free core} - A61K 9/5089: {Processes} - A61K 47/32: Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers {, poly(meth)acrylates, or polyvinyl pyrrolidone} - A61P 3/00: Drugs for disorders of the metabolism (of the blood or the extracellular fluid A61P7/00) - A61P 21/00: Drugs for disorders of the muscular or neuromuscular system - A61P 25/16: Anti-Parkinson drugs - A61K 9/5026: {obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates} - 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) - A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS ## Abstract The present invention features palatable pharmaceutical compositions including sodium phenylbutyrate and methods for the treatment of inborn errors of metabolism (e.g., Maple Syrup Urine Disease or Urea Cycle Disorders), neurodegenerative disorders such as Parkinson's disease, spinal muscular atrophy, dystonia, or inclusion-body myositis with such compositions. ## Claims ### Claim 1 A pharmaceutical composition for oral administration of sodium phenylbutyrate comprising a plurality of layered particles having a volume-based particle size distribution in which at least 90% of the layered particles in the plurality of layered particles are smaller than 500 μm, wherein each layered particle comprises (i) a seed core; (ii) a drug layer comprising the sodium phenylbutyrate; (iii) a seal coating; and (iv) a taste-mask coating, wherein the pharmaceutical composition comprises greater than 60% by total weight sodium phenylbutyrate, wherein the taste-mask coating is insoluble at a neutral pH of greater than 5 and soluble at an acidic pH of less than 2, and wherein the pharmaceutical composition comprises about 5% to 25% by total weight taste-mask coating. ### Claim 2 (depends on 1) The pharmaceutical composition of claim 1, wherein the taste-mask coating is about 5-10% of the total weight. ### Claim 3 (depends on 1) The pharmaceutical composition of claim 1, wherein the sodium phenylbutyrate comprises about 65% of the total weight. ### Claim 4 (depends on 1) The pharmaceutical composition of claim 1, wherein the drug layer comprises sodium phenylbutyrate, a binder, and a plasticizer. ### Claim 5 (depends on 4) The pharmaceutical composition of claim 4, wherein the binder is hydroxypropyl methylcellulose. ### Claim 6 (depends on 4) The pharmaceutical composition of claim 4, wherein the plasticizer is polyethylene glycol having a molecular weight between 5,000 and 7,000. ### Claim 7 (depends on 1) The pharmaceutical composition of claim 1, wherein the drug layer comprises about 65% by total weight sodium phenylbutyrate; 5 to 7% by total weight hydroxypropyl methylcellulose; and 0.1 to 1% by total weight polyethylene glycol having a molecular weight between 5,000 and 7,000. ### Claim 8 (depends on 1) The pharmaceutical composition of claim 1, wherein the taste-mask coating comprises a polymer formed from dimethylaminoethyl methacrylate, butyl methacrylate, and methyl methacrylate. ### Claim 9 (depends on 1) The pharmaceutical composition of claim 1, wherein the taste-mask coating comprises a polymer formed from dimethylaminoethyl methacrylate, butyl methacrylate, and methyl methacrylate, a plasticizer, and talc. ### Claim 10 (depends on 9) The pharmaceutical composition of claim 9, wherein the plasticizer is polyethylene glycol having a molecular weight between 5,000 and 7,000. ### Claim 11 (depends on 1) The pharmaceutical composition of claim 1, wherein the seed core is about 10 to 20% of the total weight. ### Claim 12 (depends on 11) The pharmaceutical composition of claim 11, wherein the seed core comprises microcrystalline cellulose. ### Claim 13 (depends on 1) The pharmaceutical composition of claim 1, further comprising about 8 to 10% by total weight hydroxypropyl methylcellulose. ### Claim 14 (depends on 1) The pharmaceutical composition of claim 1, further comprising about 0.5 to 3% by total weight polyethylene glycol having a molecular weight between 5,000 and 7,000. ### Claim 15 (depends on 1) The pharmaceutical composition of claim 1, wherein the taste-mask coating further comprises talc, and wherein the talc is less than about 4% by total weight. ### Claim 16 (depends on 1) The pharmaceutical composition of claim 1, wherein the seal coating is about 1-5% of the total weight. ### Claim 17 (depends on 16) The pharmaceutical composition of claim 16, wherein the seal coating comprises a water soluble polymer. ### Claim 18 (depends on 1) The pharmaceutical composition of claim 1, wherein the pharmaceutical composition comprises about 65% by total weight sodium phenylbutyrate, 8 to 10% by total weight hydroxypropyl methylcellulose, 0.5 to 3% by total weight polyethylene glycol having a molecular weight between 5,000 and 7,000, 10 to 20% by total weight microcrystalline cellulose in the seed core, less than 4% talc in the taste-mask coating, and 5 to 10% of a polymer formed from dimethylaminoethyl methacrylate, butyl methacrylate, and methyl methacrylate. ### Claim 19 (depends on 1) The pharmaceutical composition of claim 1, wherein, upon administration to a subject, said composition has equivalent distribution in plasma compared to a sodium phenylbutyrate formulation that does not comprise a taste-mask coating. ### Claim 20 (depends on 1) The pharmaceutical composition of claim 1, wherein, upon administration to a subject, said composition has greater sodium phenylbutyrate levels in the plasma at 30 minutes compared to a modified release formulation of sodium phenylbutyrate. ### Claim 21 (depends on 1) The pharmaceutical composition of claim 1, said composition scores favorably in a taste test in comparison to a sodium phenylbutyrate formulation that does not comprise a taste-mask coating. ### Claim 22 (depends on 1) The pharmaceutical composition of claim 1, wherein taste-masking coating is insoluble at pH 6.5-7.5. ### Claim 23 (depends on 1) The pharmaceutical composition or claim 1, wherein the taste-mask coating is soluble at a pH of less than 2. ### Claim 24 (depends on 1) The pharmaceutical composition of claim 1, taste-mask coasting is soluble at pH 1-2.