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WO1996030011A1 - Compositions antimycosiques pour application locale - Google Patents

Compositions antimycosiques pour application locale Download PDF

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Publication number
WO1996030011A1
WO1996030011A1 PCT/US1996/004390 US9604390W WO9630011A1 WO 1996030011 A1 WO1996030011 A1 WO 1996030011A1 US 9604390 W US9604390 W US 9604390W WO 9630011 A1 WO9630011 A1 WO 9630011A1
Authority
WO
WIPO (PCT)
Prior art keywords
nail
composition
dimethyl sulfoxide
pharmaceutical composition
epinychium
Prior art date
Application number
PCT/US1996/004390
Other languages
English (en)
Inventor
Joseph S. Giacalone
Original Assignee
Bioplex, L.C.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bioplex, L.C. filed Critical Bioplex, L.C.
Publication of WO1996030011A1 publication Critical patent/WO1996030011A1/fr

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
    • A61K31/343—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide condensed with a carbocyclic ring, e.g. coumaran, bufuralol, befunolol, clobenfurol, amiodarone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4164—1,3-Diazoles
    • A61K31/4174—Arylalkylimidazoles, e.g. oxymetazolin, naphazoline, miconazole
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4196—1,2,4-Triazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/513—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim having oxo groups directly attached to the heterocyclic ring, e.g. cytosine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/20—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing sulfur, e.g. dimethyl sulfoxide [DMSO], docusate, sodium lauryl sulfate or aminosulfonic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q3/00—Manicure or pedicure preparations

Definitions

  • the invention relates to certain methods and compositions for the treatment of onychomycoses (i.e. fungal infections of the toenail or fingernail).
  • onychomycoses i.e. fungal infections of the toenail or fingernail.
  • Subjects who are immunocompromised are especially susceptible to such infections. Diabetes, drug (e.g. cancer chemotherapy) therapy, AIDS, and other disease states can immunocompromise a subject, and the occurrence of onychomycoses in these groups of people is greater than the population as a whole.
  • Griseofiilvin is one oral antifungal agent that is produced by, for example, Penicillium griseofurvum Dierck or Penicillinm jaczewski Zal. (see, e.g. U.S. Patent 3,607,656 to Laine et al., patented Sept. 21, 1971).
  • DMSO has been studied to assess how it might influence permeation through the human nail. Walters et al. "Solvent Effects on Nail Permeation", Journal of Pharmacy & Pharmacology. 37:771-775 (1985). DMSO was found to retard permeation rates of model molecules such as methanol and hexanol. Id. A need exists for a once daily, relatively cost-effective therapy for effectively treating toenail or fingernail fungal infections in a way that does not necessarily involve avulsion or debridement of the affected nail or nails.
  • an effective treatment for onychomycosis which need not involve avulsion of the nail.
  • the treatment involves topically applying an antifungal agent dissolved in a dimethyl sulfoxide solution, on a regular basis, to the nail and to the nail's epinychium.
  • the antifungal agent is present in the composition in at least a minimum inhibitory concentration for the antirnycotic agent for the particular fungus when the antifungal agent is dissolved in DMSO.
  • the composition is applied to the infected nail and epinychium on a no more than once daily basis, and the infected nail need not necessarily be removed by avulsion or debridement.
  • the invention thus includes a method of treating or preventing onychomycosis, associated pharmaceutical compositions for treating or preventing onychomycosis (especially ones conta ing dimethyl sulfoxide and from about 0.1 % to about 10% by weight griseofiilvin), and methods of making the pharmaceutical compositions.
  • Antifungal agents include both fungistatic compounds (i.e. such compounds merely inhibit the growth of the fungus without killing it) and fungicidal compounds.
  • Specific antifungal agents include flucytosine (also known as 5-fluorocytosine in amounts generally ranging from lmg/ml to lOmg/ml by weight of the composition), griseofiilvin, polyene macrolide antibiotics, especially the heptaenes (e.g.
  • amphotericin B the imidazole derivatives such as ticonazole, clotrimazole, econazole, oxiconazole, isoconazole, and miconazole
  • imidazole derivatives such as ticonazole, clotrimazole, econazole, oxiconazole, isoconazole, and miconazole
  • bifonazole U.S. Patent 4,118,487 to criz et al., patented Oct. 3, 1978
  • itraconazole U.S.
  • thiocarbamic acid derivatives such as tolnaftate
  • terbinafine forms of which are available from Sandoz under the trade designation LAMASIL
  • pharmaceutically acceptable salts e.g. acid addition salts
  • pharmaceutically acceptable acid addition salts include salts of inorganic acids such as sulfuric, nitric, phosphoric, and preferably hydrochloric acid, as well as organic acids such as acetic, propionic, succinic, fumaric, maleic, citric, tartaric, cinnamic, lactic, mandelic, and ethanedisulfonic acid.
  • the salts may be made by reacting the free base of the particular antifungal agent with the chosen acid in a stoichiometric ratio in an appropriate solvent.
  • the DMSO to be incorporated into the inventive compositions is preferably of a purified grade (i.e. not a technical grade), which means that it should be sufficiently purified so that it does not cause any untoward reaction or injury to the body of the subject from contaminants and the like.
  • a purified grade i.e. not a technical grade
  • Various methods of purifying technical grade DMSO are known (see, e.g. U.S. Patent 3,358,036), and include fractional distillation, solvent extraction, and freezing.
  • Concentrations of DMSO incorporated into the topical pharmaceutical compositions of the invention will preferably be of greater than 90% (e.g. 100%) strength.
  • solutions containing at least about 50 % DMSO along with a minor amount of a pharmaceutically acceptable diluent such as ethanol, n-propanol, isopropanol, propylene glycol, or glycerol.
  • solutions containing more than 50% DMSO by weight as a solvent for the composition are "dimethyl sulfoxide solutions”.
  • Dimethyl sulfoxide solutions containing greater than 90% DMSO may cause some skin drying and irritation.
  • the amount of diluent should be chosen so as not to interfere with the solubility of the particular antifungal agent.
  • the dimethyl sulfoxide solution preferably contains, by weight, from 80% to 100% dimethyl sulfoxide.
  • Concentrations of the antifungal agents in the composition will of course vary dependent on the antifungal agent and (possibly) salt used. Concentrations will preferably be at least at high as the respective compound or compounds' minimum inhibitory concentration ("MIC") for fungi, and more preferably at least as great as the respective compound or compounds' minimum fungicidal concentration ("MFC”) in DMSO.
  • the antifungal compositions will be present in the inventive compositions in an amount varying from 0.1 to 50 weight percent, preferably 1 to 10 weight percent, of the total composition.
  • compositions may also contain pharmaceutical necessities such as thickening agents and preservatives.
  • the invention also includes the use of the components of the herein described compositions (e.g. dimethyl sulfoxide solution and antimycotic agent or agents) in the manufacture of a medicament for the treatment or prophylaxis of onychomycoses. Once made, the composition may be used to treat or prophylax against onychomycosis.
  • a method of treating a fungal infection of a nail, without avulsing the nail includes topically applying to the nail and to the nail's epinychium, on a regular basis (e.g. one to three times a week, although for convenience's sake, it may be applied on a more frequent e.g. daily basis), a composition comprising an antimycotic agent dissolved in a dimethyl sulfoxide solution. The antimycotic agent is present in the composition at an MIC for the antimycotic agent.
  • composition may be accomplished by eye-dropper, Q- TrP -like swab, brush (e.g. such as a nail polish brush, aerosol, atomizer, dipping, a nail-sized transdermal drug delivery pad containing the two compounds, and equivalent structure.
  • brush e.g. such as a nail polish brush, aerosol, atomizer, dipping, a nail-sized transdermal drug delivery pad containing the two compounds, and equivalent structure.
  • the treated area may (but need not) be occluded by subsequent application of a bandage, tape, cotton, or nail cap.
  • Prophylaxis will be especially of the nails adjacent to fungally infected nails.
  • the composition need not be applied as often (e.g. once to three times a week).
  • Typical candidates for prophylaxis include the elderly and patients suffering from HIN, diabetes, peripheral vascular disease, or undergoing immunosuppressive therapy.
  • Packaging for the composition will typically include a glass or other inert container for the composition as well as one of the aforementioned applicators and instructions for using the composition either to treat onychomycosis or prevent its occurrence.
  • This packaging may further include material to occlude the nail after treatment or prophylaxis.
  • EXAMPLE I A composition comprising 660 mg of ultramicrosize griseofiilvin dissolved in 30 ml DMSO was made. 2 tablets of FULNICI ⁇ TM P/G 330 griseofiilvin USP (available from Schering Corporation of Kenilworth, ⁇ J, USA) were ground and dissolved in 30 ml of 99% DMSO. EXAMPLE ⁇
  • EXAMPLE I The composition of EXAMPLE I was applied daily to the top of the nail and the epinychium of ten subjects ranging in age from 25 to 70 years old, all of whom were suffering from onychomycoses. Beneficial results were seen in all patients in 3 to 4 weeks. All new nail growth was noted to be fungus-free. No relapses were seen after one year.
  • EXAMPLE m A composition comprising 200 mg of fluconazole dissolved in 30 ml DMSO was made. 4 tablets (50 mg each) of DIFLUCANTM fluconazole USP (available from Roerig Division of Pfizer Labs, of New York, NY, USA) were ground and dissolved in 30 ml of DMSO.
  • DIFLUCANTM fluconazole USP available from Roerig Division of Pfizer Labs, of New York, NY, USA
  • composition of EXAMPLE in was applied daily to the top of the nail and the epinychium of five subjects suffering from onychomycosis. Beneficial results were seen in all patients in three weeks.
  • a composition containing 750 mg of flucytosine dissolved in 30 ml DMSO is made by dissolving the contents of three 250 mg capsules of ANCOBONTM flucytosine USP (available from Roche Labs, of Nutley, NJ, USA) into 30 ml of DMSO (density 1.0955 g/ml).
  • EXAMPLE VI A composition containing 200 mg of amphotericin B dissolved in 30 ml DMSO is made by dissolving the already lyophilized contents of 4 vials of FUNGIZONETM Intravenous amphotericin B USP (available from Apothecon of Princeton, NJ, USA) in 30 ml of DMSO.
  • EXAMPLE VH A composition containing 200 mg of itraconazole dissolved in 30 ml DMSO is made by dissolving the contents of two 100 mg capsules of SPORANAXTM itraconazole USP (available from Janssen Pharmaceutica of Titusville, NJ, USA) into 30 ml of DMSO.
  • EXAMPLE VIE A composition containing 400 mg of ketoconazole dissolved in 30 ml DMSO is made by crushing two 200 mg tablets of NIZORALTM ketoconazole USP (available from Janssen Pharmaceutica of Titusville, NJ, USA) and dissolving the crushed tablets into 30 ml of DMSO.
  • EXAMPLE LX A composition containing 1000 mg of clotrimazole dissolved in 30 ml DMSO is made by dissolving 1000 mg of clotrimazole USP into 30 ml of DMSO.
  • EXAMPLE X The composition of EXAMPLE Vm is placed into a brown glass bottle having a brush associated with its lid. Instructions for once daily use of the composition are included on a label associated with the bottle.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Birds (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Dermatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Traitement et prophylaxie efficaces de l'onychomycose consistant en une application locale régulière d'un agent antifongique dissout dans une solution de sulfoxide de diméthyle (DMSO) sur l'ongle et, en particulier, sur la cuticule de l'ongle. Cet agent antifongique est présent dans la composition à raison d'une concentration minimum ayant un effet inhibiteur pour le champignon visé lorsque l'agent antifongique est dissous dans le DMSO. Ladite composition peut être appliquée sur l'ongle et la cuticule sur une base journalière ou moins fréquente, l'ongle ainsi atteint ne devant pas être enlevé. L'invention porte également sur des méthodes de traitement ou de prévention de l'onychomycose, liées à des compositions pharmaceutiques de traitement ou de prévention de l'onychomycose (en particulier sur des compositions contenant du DMSO et de 2 à 10 % en poids de griséofulvine), et sur des méthodes de préparation de ces compositions pharmaceutiques.
PCT/US1996/004390 1995-03-30 1996-03-29 Compositions antimycosiques pour application locale WO1996030011A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US41363695A 1995-03-30 1995-03-30
US413,636 1995-03-30

Publications (1)

Publication Number Publication Date
WO1996030011A1 true WO1996030011A1 (fr) 1996-10-03

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PCT/US1996/004390 WO1996030011A1 (fr) 1995-03-30 1996-03-29 Compositions antimycosiques pour application locale

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GR980100028A (el) * 1998-01-15 1999-09-30 Drug Research Hellas ����� Φαρμακευτικα προιοντα για τοπικη χρηση που περιεχουν φλουκοναζολη σε συγκεντρωσεις μεταξυ 0,2% και 5%
US6932861B2 (en) 2000-11-28 2005-08-23 Fmc Corporation Edible PGA coating composition
WO2009071959A3 (fr) * 2007-12-04 2009-11-26 Pannonpharma Gyógyszergyártó Kft. Composition sous forme d'une teinture pour peinture ou d'une laque permettant de traiter des infections fongiques, qui contient de l'itraconazole, et procédé pour la préparer
US10105444B2 (en) 2010-07-08 2018-10-23 Dow Pharmaceutical Sciences, Inc. Compositions and methods for treating diseases of the nail
US10245257B2 (en) 2013-11-22 2019-04-02 Dow Pharmaceutical Sciences, Inc. Anti-infective methods, compositions, and devices
US10342875B2 (en) 2013-10-03 2019-07-09 Dow Pharmaceutical Sciences, Inc. Stabilized efinaconazole compositions
US10512640B2 (en) 2008-01-03 2019-12-24 Dow Pharmaceutical Sciences, Inc. Compositions and methods for treating diseases of the nail

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5264206A (en) * 1987-06-16 1993-11-23 Hoechst Aktiengesellschaft Nail lacquer with antimycotic activity, and a process for the preparation thereof

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5264206A (en) * 1987-06-16 1993-11-23 Hoechst Aktiengesellschaft Nail lacquer with antimycotic activity, and a process for the preparation thereof

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GR980100028A (el) * 1998-01-15 1999-09-30 Drug Research Hellas ����� Φαρμακευτικα προιοντα για τοπικη χρηση που περιεχουν φλουκοναζολη σε συγκεντρωσεις μεταξυ 0,2% και 5%
US6932861B2 (en) 2000-11-28 2005-08-23 Fmc Corporation Edible PGA coating composition
WO2009071959A3 (fr) * 2007-12-04 2009-11-26 Pannonpharma Gyógyszergyártó Kft. Composition sous forme d'une teinture pour peinture ou d'une laque permettant de traiter des infections fongiques, qui contient de l'itraconazole, et procédé pour la préparer
US10512640B2 (en) 2008-01-03 2019-12-24 Dow Pharmaceutical Sciences, Inc. Compositions and methods for treating diseases of the nail
US11872218B2 (en) 2008-01-03 2024-01-16 Bausch Health Ireland Limited Compositions and methods for treating diseases of the nail
US11213519B2 (en) 2008-01-03 2022-01-04 Bausch Health Ireland Limited Compositions and methods for treating diseases of the nail
US10105444B2 (en) 2010-07-08 2018-10-23 Dow Pharmaceutical Sciences, Inc. Compositions and methods for treating diseases of the nail
US10828369B2 (en) 2010-07-08 2020-11-10 Dow Pharmaceutical Sciences, Inc. Compositions and methods for treating diseases of the nail
US10864274B2 (en) 2013-10-03 2020-12-15 Bausch Health Ireland Limited Stabilized efinaconazole formulations
US10342875B2 (en) 2013-10-03 2019-07-09 Dow Pharmaceutical Sciences, Inc. Stabilized efinaconazole compositions
US12076404B2 (en) 2013-10-03 2024-09-03 Bausch Health Ireland Limited Stabilized efinaconazole compositions as antifungals
US10828293B2 (en) 2013-11-22 2020-11-10 Dow Pharmaceutical Sciences, Inc. Anti-infective methods, compositions, and devices
US11654139B2 (en) 2013-11-22 2023-05-23 Bausch Health Ireland Limited Anti-infective methods, compositions, and devices
US10245257B2 (en) 2013-11-22 2019-04-02 Dow Pharmaceutical Sciences, Inc. Anti-infective methods, compositions, and devices

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