# US 11,026,893 B2 · Taste masking drug formulations

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- Number: US 11,026,893 B2
- Document ID: US11026893B2
- Status: Granted
- Kind: B2
- Application number: 16/542,986
- Filed: 2019-08-16
- Published: 2019-12-05
- Granted: 2021-06-08
- Earliest claimed: 2014-02-25
- Assignees: Adare Pharmaceuticals USA, Inc.
- Applicants: Adare Pharmaceuticals USA, Inc.
- Inventors: Cory Berkland; Milind Singh
- Web page: https://patentgrep.com/patent/US11026893B2

## CPC

- A61K 9/5026: {obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates}
- A61K 9/0053: {Mouth and digestive tract, i.e. intraoral and peroral administration}
- A61K 9/5015: {Organic compounds, e.g. fats, sugars}
- A61K 9/5063: {Compounds of unknown constitution, e.g. material from plants or animals (oils, fats, waxes, shellac A61K9/5015)}
- A61K 9/5089: {Processes}
- A61K 31/426: 1,3-Thiazoles
- A61K 31/573: substituted in position 21, e.g. cortisone, dexamethasone, prednisone or aldosterone
- A61K 47/10: Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
- 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

The present disclosure relates to a taste-masking microcapsule composition. The composition comprises a core portion encapsulated by a shell portion. The core portion comprises an active pharmaceutical ingredient (API) and one or more excipients. The shell portion comprises a hydrophobic matrix and a pH-responsive material. The microcapsule compositions prevent API release at the more neutral pH levels in the oral cavity, but upon exposure to pH levels of the stomach, the pH-responsive material becomes soluble thereby permitting release of the API.

## Claims

### Claim 1

A method for producing a microcapsule comprising the following steps:
(1) dissolving an active pharmaceutical ingredient in ethanol to produce an active pharmaceutical ingredient-ethanol mixture;
(2) co-melting the active pharmaceutical ingredient-ethanol mixture with a hydrophilic excipient to provide a core dispersion;
(3) melting a pH-responsive material and a hydrophobic material comprising a wax or lipid to form a shell mixture which comprises about 1% to 25% by weight of the pH-responsive material in a hydrophobic matrix; and
(4) applying the core dispersion through a central portion of a nozzle and simultaneously applying the shell mixture through an annular portion of the nozzle surrounding the central portion in the presence of vibrational excitation thereby forming the microcapsule, wherein the microcapsule comprises a core portion and a shell portion.

### Claim 2 (depends on 1)

The method of claim 1 further comprising the step of applying a stabilizing air stream to the nozzle as the microcapsule exits the nozzle to reduce the diameter of the microcapsule.

### Claim 3 (depends on 1)

The method of claim 1, wherein the hydrophilic excipient is one or more selected from the group consisting of polyethylene glycol, polyols, and poloxamer and lutrol block copolymers.

### Claim 4 (depends on 1)

The method of claim 1 wherein the active pharmaceutical ingredient is hydrophobic.

### Claim 5 (depends on 1)

The method of claim 1 wherein the pH-responsive material comprises a methacrylate copolymer, butylated methacrylate copolymer, basic butylated methacrylate copolymer, poly(methacrylic acid), amino methacrylate copolymer, aminoalkyl methacrylate copolymer, hydroxypropylmethyl cellulose phthalate, hypomellose phthalate, polyacrylate derivative or polymethacrylate derivative, and the hydrophobic matrix comprises a wax, lipid or combination thereof.

### Claim 6 (depends on 1)

The method of claim 1 wherein the hydrophobic material is carnauba wax, beeswax, or a combination thereof.

### Claim 7 (depends on 1)

The method of claim 1 wherein the hydrophobic material further comprises stearic acid.

### Claim 8 (depends on 1)

The method of claim 1 wherein the pH-responsive material comprises a butylated methacrylate copolymer and the hydrophobic material comprises stearic acid.

### Claim 9 (depends on 1)

The method of claim 1 wherein the active pharmaceutical ingredient is prednisone or ritonavir.

### Claim 10 (depends on 1)

The method of claim 1 wherein the microcapsule has a mean particle diameter from about 100 μm to about 400 μm.

### Claim 11 (depends on 1)

The method of claim 1, further comprising the step of suspending a plurality of the microcapsules in a liquid suspension.

### Claim 12 (depends on 1)

The method of claim 1, further comprising the step of formulating a plurality of the microcapsules as a dry powder.

### Claim 13 (depends on 1)

The method of claim 1 wherein the shell portion comprises from about 1% to 10% by weight of the pH-responsive material.

### Claim 14 (depends on 1)

The method of claim 1 wherein the hydrophobic matrix further comprises a glycerol fatty acid ester, a cellulose ether, or a cellulose ester.

### Claim 15 (depends on 14)

The method of claim 14 wherein the glycerol fatty acid ester is glycerol monostearate or a sorbitan ester.