IP Library Granted Patent US 11,026,893
Granted Patent B2
US 11,026,893 · App. 16/542,986 · Granted Jun 8, 2021

Taste masking drug formulations

Inventors: Cory Berkland (Lawrence, KS); Milind Singh (Apex, NC)
Assignee: Adare Pharmaceuticals USA, Inc.
A61K9/5026A61K9/0053A61K9/5015A61K9/5063A61K9/5089A61K31/426A61K31/573A61K47/10
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Quick Facts
Patent No.
US 11,026,893
App. No.
16/542,986
Granted
Jun 8, 2021
Kind
B2
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 (19)

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.

2. 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.

3. 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.

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

5. 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.

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

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

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

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

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

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

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

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

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

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

Assignments (6)
SECURITY INTEREST Recorded Nov 8, 2022
From: ADARE PHARMACEUTICALS, INC.; ADARE PHARMACEUTICALS USA, INC.
To: TEAL MIDCO HOLDINGS, L.P.
Reel/Frame 061698/0541 →
RELEASE OF SECURITY INTEREST RECORDED AT REEL/FRAMES 037246/0313, 047807/0967, 053474/0276 Recorded Sep 22, 2020
From: BANK OF MONTREAL, AS COLLATERAL AGENT
To: ADARE PHARMACEUTICALS, INC.; ADARE DEVELOPMENT I, L.P.; ADARE PHARMACEUTICALS USA, INC.
Reel/Frame 053852/0697 →
SECURITY INTEREST Recorded Sep 22, 2020
From: ADARE PHARMACEUTICALS, INC.; ADARE PHARMACEUTICALS USA, INC.
To: CRESCENT AGENCY SERVICES LLC, AS ADMINISTRATIVE AGENT AND COLLATERAL AGENT
Reel/Frame 053849/0967 →
CHANGE OF NAME Recorded Sep 18, 2020
From: ORBIS BIOSCIENCES, INC.
To: ADARE PHARMACEUTICALS USA, INC.
Reel/Frame 053819/0832 →
SECURITY INTEREST Recorded Aug 12, 2020
From: ADARE PHARMACEUTICALS USA, INC.
To: BANK OF MONTREAL
Reel/Frame 053474/0276 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 1, 2019
From: BERKLAND, CORY; SINGH, MILIND
To: ORBIS BIOSCIENCES, INC.
Reel/Frame 050894/0601 →