IP Library Granted Patent US 11,185,479
Granted Patent B2
US 11,185,479 · App. 16/577,312 · Granted Nov 30, 2021

Buffered microencapsulated compositions and methods

Inventors: Mark A. Latta (Omaha, NE); Stephen M. Gross (Omaha, NE); William A. McHale (Collegeville, PA)
Assignee: Premier Dental Products Company
A61K8/11A61K6/20A61K6/69A61K6/71A61K8/19A61K8/21A61K8/24A61K8/64A61K8/87A61K9/0056A61K9/5031A61K9/5089A61K33/06A61K33/16A61K33/44A61K47/02A61Q3/02A61Q5/02A61Q5/06A61Q5/12A61Q11/00A61Q19/00A61K2800/412
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Quick Facts
Patent No.
US 11,185,479
App. No.
16/577,312
Granted
Nov 30, 2021
Kind
B2
Abstract

A microcapsule composition comprising at least one polymer substantially disposed as a semipermeable shell around a buffered solution and at least one therapeutic agent, wherein the therapeutic agent permeates the shell, and wherein the composition is suitable for topical epithelial cells of mammal.

Claims (21)

1. A topical microcapsule composition comprising an antibacterial agent comprising:

a plurality of microcapsules and a carrier,

each of said microcapsules comprising at least one polymer substantially disposed as a semipermeable shell around a buffered solution,

said microcapsule composition comprising at least a first subset of microcapsules, wherein the first subset of microcapsules comprises within each of said microcapsules the antibacterial agent for topical use on epithelial tissue;

wherein the antibacterial agent permeates the shell.

2. The microcapsule composition of claim 1 wherein the buffered solution is an aqueous solution.

3. The microcapsule composition of claim 1 wherein the antibacterial agent is a natural antimicrobial agent selected from the group consisting of: beta lactam antibiotics, penicillins cephalosporins, protein synthesis inhibitors, aminoglycosides, macrolides, ketolides, tetracyclines, chloramphenicol, polypeptides, penicillin G, procaine penicillin, benzathine penicillin, penicillin V, cefacetrile, cefadroxil, cephalexin, cefaloglycin, cefalonium, cefaloridine, cefalotin, cefapirin, cefatrizine, cefazaflur, cefazedone, cefazolin, cefradine, cefroxadine, ceftezole, cefaclor, cefonicid, cefprozil, cefuroxime, cefuzonam, cefmetazole, cefotetan, cefoxitin, amikacin, arbekacin, gentamicin, kanamycin, neomycin, netilmicin, paromomycin, rhodostreptomycin, streptomycin, tobramycin, apramycin, azithromycin, clarithromycin, dirithromycin, erythromycin, roxithromycin, telithromycin, telithromycin, cethromycin, solithromycin, spiramycin, ansamycin, oleandomycin, carbomycin, tylosin, tetracycline, chlortetracycline, oxytetracycline, demeclocycline doxycycline, lymecycline, meclocycline, methacycline, minocycline, rolitetracycline, actinomycin, bacitracin, colistin, polymyxin B, sulphonamides, cotrimoxazole, quinolones, sulfamethoxazole, sulfisomidine, sulfacetamide, sulfadoxine, dichlorphenamide, dorzolamide, acetazolamide, bumetanide, chlorthalidone, clopamide, furosemide, hydrochlorothiazide, indapamide, mefruside, metolazone, xipamide, acetazolamide, ethoxzolamide, sultiame, zonisamide, celecoxib, darunavir, probenecid, sulfasalazine, and sumatriptan.

4. A method of forming a topical microcapsule composition comprising a plurality of microcapsules: said plurality of microcapsules being formed by combining a polymer and at least one buffered aqueous solution comprising a therapeutic agent, by contacting: (a) said buffered solution comprising the therapeutic agent, (b) an oil phase, (c) said polymer, and (d) an emulsifying agent, wherein the polymer substantially forms a semipermeable shell around the buffered aqueous solution; and adding said plurality of microcapsules to a carrier.

5. The method of claim 4 wherein said plurality of microcapsules comprises a first and a second plurality of microcapsules, wherein a first plurality of microcapsules is formed using a first therapeutic agent, and a second plurality of microcapsules is formed using a second therapeutic agent.

6. The method of claim 5 wherein the first and second pluralities of microcapsules have a different release profile.

7. The method of claim 4 further comprising a diol, an isocyanate, or both, wherein said diol, isocyanate, or both increases the molecular weight of the semipermeable shell.

8. The method of claim 4 wherein the oil phase is methyl benzoate.

9. The method of claim 4 wherein the emulsifying agent is a polyglyceryl-3-polyricinoleate.

10. The method of claim 4 wherein said therapeutic agent is selected from the group consisting of: antibacterial agents, antifungal agents, benzoyl peroxide, coal tar, corticosteroids, retinoids, salicylic acid, antiviral agents, immunosuppressants, and biologic agents for treating psoriasis.

11. The method of claim 4 wherein the carrier is in the form of a moisturizer, cream, lotion, foam, gel, shampoo, hair conditioner, hair gel, or a nail polish.

12. The method of claim 4 wherein the therapeutic agent is a biologically active additive or a peptide-based or peptide analog-based antimicrobial agent.

13. The method of claim 4 further comprising a natural oil, a synthetic oil, flavoring oils, flavoring aldehydes, esters, alcohols, vanillin, sage, marjoram, parsley oil, spearmint oil, cinnamon oil, oil of wintergreen, peppermint oil, clove oil, bay oil, anise oil, eucalyptus oil, citrus oil, lemon oil, orange oil, lime oil, grapefruit oil, apricot oil, banana oil, grape oil, apple oil, strawberry oil, cherry oil, pineapple oil, bean-derived oil, nut-derived oil, cocoa oil, cola oil, peanut oil, almond oil, and combinations thereof.

14. The method of claim 4 wherein the therapeutic agent is selected from the group consisting of: menthol, menthyl acetate, menthyl lactate, camphor, eucalyptus oil, eucalyptol, anethole, eugenol, cassia , oxanone, a-irisone, propenyl guaiethol, thymol, linalool, benzaldehyde, cinnamaldehyde, N-ethyl-p-menthan-3-carboxamine, N,2,3trimethyl-2-isopropylbutanamide, 3-1-menthoxypropane-1,2-diol, cinnamaldehyde glycerol acetal (CGA), methone glycerol acetal (MGA), and combinations thereof.

15. The method of claim 4 wherein the therapeutic agent is selected from the group consisting of: butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), vitamin A, carotenoids, vitamin E, flavonoids, polyphenols, ascorbic acid, herbal antioxidants, chlorophyll, melatonin, and combinations thereof.

16. The method of claim 4 wherein the therapeutic agent is selected from the group consisting of: salicylanilides, carbanilides, bisphenols, diphenyl ethers, anilides of thiophene carboxylic acids, chlorhexidines, alkyl ammonium, pyridinium, isoquinolinium salts, thiuram sulfides, dithiocarbamates, and combinations thereof.

17. The method of claim 4 wherein the therapeutic agent is selected from the group consisting of: a natural antimicrobial agent selected from the group consisting of: beta lactam antibiotics, penicillins, cephalosporins, protein synthesis inhibitors, aminoglycosides, macrolides, ketolides, tetracyclines, chloramphenicol, polypeptides, penicillin G, procaine penicillin, benzathine penicillin, penicillin V, cefacetrile, cefadroxil, cephalexin, cefaloglycin, cefalonium, cefaloridine, cefalotin, cefapirin, cefatrizine, cefazaflur, cefazedone, cefazolin, cefradine, cefroxadine, ceftezole, cefaclor, cefonicid, cefprozil, cefuroxime, cefuzonam, cefmetazole, cefotetan, cefoxitin, amikacin, arbekacin, gentamicin, kanamycin, neomycin, netilmicin, paromomycin, rhodostreptomycin, streptomycin, tobramycin, apramycin, azithromycin, clarithromycin, dirithromycin, erythromycin, roxithromycin, telithromycin, telithromycin, cethromycin, solithromycin, spiramycin, ansamycin, oleandomycin, carbomycin, tylosin, tetracycline, chlortetracycline, oxytetracycline, demeclocycline, doxycycline, lymecycline, meclocycline, methacycline, minocycline, rolitetracycline, actinomycin, bacitracin, colistin, polymyxin B, sulphonamides, cotrimoxazole, quinolones, antivirals, antifungals, anticancer drugs, antimalarials, antituberculosis drugs, antileprotics, antiprotozoals, sulfamethoxazole, sulfisomidine, sulfacetamide, sulfadoxine, dichlorphenamide, dorzolamide, acetazolamide, bumetanide, chlorthalidone, clopamide, furosemide, hydrochlorothiazide, indapamide, mefruside, metolazone, xipamide, acetazolamide, ethoxzolamide, sultiame, zonisamide, celecoxib, darunavir, probenecid, sulfasalazine, and sumatriptan.

Assignments (3)
SECURITY INTEREST Recorded Mar 27, 2025
From: PREMIER DENTAL PRODUCTS COMPANY, LLC
To: FIDELITY DIRECT LENDING LLC, AS ADMINISTRATIVE AGENT
Reel/Frame 070650/0397 →
ENTITY CONVERSION Recorded Mar 17, 2025
From: PREMIER DENTAL PRODUCTS COMPANY
To: PREMIER DENTAL PRODUCTS COMPANY, LLC
Reel/Frame 070537/0105 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 25, 2020
From: LATTA, MARK A.; GROSS, STEPHEN M.; MCHALE, WILLIAM A.
To: PREMIER DENTAL PRODUCTS COMPANY
Reel/Frame 053034/0425 →
Continuity (7)
Division 16207515 · Dec 3, 2018
Continuation 15921269 · Mar 14, 2018
Division 15791554 · Oct 24, 2017
Division 13619128 · Sep 14, 2012
Continuation In Part 12768696 · Apr 27, 2010
Provisional Application 61172939 · Apr 27, 2009
Related Publication 20200016050A1 · Jan 16, 2020