Topical Antifungal Composition Topische Antimykotische Zusammensetzung Composition Antifongique Topique

Topical Antifungal Composition Topische Antimykotische Zusammensetzung Composition Antifongique Topique

(19) TZZ __T (11) EP 2 451 468 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: A61K 36/53 (2006.01) A61K 36/534 (2006.01) 11.01.2017 Bulletin 2017/02 A61K 36/14 (2006.01) A61K 36/15 (2006.01) A61K 36/23 (2006.01) A61K 36/235 (2006.01) (2006.01) (2006.01) (21) Application number: 10731892.5 A61K 36/54 A61K 36/61 A61K 31/045 (2006.01) A61K 31/05 (2006.01) A61P 31/00 (2006.01) (22) Date of filing: 06.07.2010 (86) International application number: PCT/US2010/041050 (87) International publication number: WO 2011/005749 (13.01.2011 Gazette 2011/02) (54) TOPICAL ANTIFUNGAL COMPOSITION TOPISCHE ANTIMYKOTISCHE ZUSAMMENSETZUNG COMPOSITION ANTIFONGIQUE TOPIQUE (84) Designated Contracting States: (56) References cited: AL AT BE BG CH CY CZ DE DK EE ES FI FR GB WO-A1-2005/087244 WO-A2-96/37210 GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO WO-A2-2004/076680 PL PT RO SE SI SK SM TR • DALLEAU S ET AL: "In vitro activity of essential (30) Priority: 08.07.2009 US 223870 P oils and their major components against Candida albicans yeasts growing planktonically and as (43) Date of publication of application: biofilms" INTERNATIONAL JOURNAL OF 16.05.2012 Bulletin 2012/20 ANTIMICROBIAL AGENTS, vol. 29, no. Suppl. 2, March 2007 (2007-03), page S147, XP22037821 & (73) Proprietor: Onikolabs LLC 17TH EUROPEAN CONGRESS OF CLINICAL Cincinnati, OH 45249-1211 (US) MICROBIOLOGY AND INFECTIOUS DISEASES/25TH INTERNATIONAL CONGRESS; (72) Inventor: BOEGLI, Charles, J. MUNICH, GERMANY; MARCH 31 -APRIL 03, 2007 Cincinnati ISSN: 0924-8579 OH 45249-1211 (US) • KALEMBA D ET AL: "ANTIBACTERIAL AND ANTIFUNGAL PROPERTIES OF ESSENTIAL (74) Representative: Samson & Partner Patentanwälte OILS" CURRENT MEDICINAL CHEMISTRY, mbB BENTHAMSCIENCE PUBLISHERS BV, BE LNKD- Widenmayerstraße 6 DOI:10.2174/0929867033457719, vol. 10, no. 10, 1 80538 München (DE) January 2003 (2003-01-01), pages 813-829, XP008056360 ISSN: 0929-8673 Remarks: Thefile contains technical information submitted after the application was filed and not included in this specification Note: Within nine months of the publication of the mention of the grant of the European patent in the European Patent Bulletin, any person may give notice to the European Patent Office of opposition to that patent, in accordance with the Implementing Regulations. Notice of opposition shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 2 451 468 B1 Printed by Jouve, 75001 PARIS (FR) EP 2 451 468 B1 Description BACKGROUND OF THE INVENTION 5 [0001] Many of the commonly used antimicrobial agents are synthetic compounds. In recent years, there has been an increased interest in avoiding or eliminating the use of synthetic compounds and in developing and promoting the use of natural materials. Consumers generally consider plant materials less toxic and a more suitable natural alternative to synthetic compounds. [0002] Various herbal and plant preparations are known for certain uses. For example, Listerine® antiseptic mouthwash 10 is a known composition containing thyme oil, eucalyptus oil, methyl salicylate (wintergreen oil), and menthol in an alcohol solution. This composition is produced as an oral hygiene composition. Various reports have been produced showing Listerine® causes a reduction in plaque and gingivitis. Although various other plant compositions have been produced, many of the commercially available compositions have not shown substantial antimicrobial activity. [0003] The body normally serves as host for a variety of bacteria and fungi. Most of the time, the balance between 15 the body as host and the microorganisms is maintained. Sometimes, however, conditions exist that permit the microor- ganisms to tip that balance, causing an infection. Such fungi are only problematic when they grow in an uncontrolled manner, causing various diseases as well as discomfort for the infected human or animal. Unfortunately, uncontrolled fungal growths regularly occur, making topical anti-fungal preparations one of the largest segments of the market for topical external products. 20 [0004] Once fungal populations have become uncontrolled, the resultant infection is difficult to treat successfully. Synthetic topical antifungal preparations are commonly used for treatment. However, such infections are often recurrent and require a prolonged treatment regimen. Some consumers find prolonged treatment using synthetic products unde- sirable. [0005] Certain fungal infections of the skin known as tinea infections are caused by dermatophytes, which are members 25 of the Trichophyton, Microsporum and Epidermophyton species. These mold-like fungi thrive in warm, moist areas, thriving on the dead tissues of hair, nails, and outer skin layers. Tinea infections include tinea pedis, known as athlete’s foot; tinea corporis, known as ringworm; tinea capitis, a fungal infection of the scalp that can cause hair loss; tinea cruris, known as jock itch or tinea of the groin; tinea unguum, which is tinea of the nails; and tinea versicolor, a superficial fungal infection that produces brown, tan, or white spots on the trunk of the body. Tinea infections are contagious and can be 30 passed through direct contact or by contact with clothing, from shower and pool surfaces, and even from pets. [0006] Athlete’s foot or tinea pedis is by far the most common form, with more than 12 million people in the United States suffering from the disease per year. It presents with redness, itching, burning, cracking, scaling, swelling and occasionally bleeding. The condition generally includes small vesicles, fissures, scaling, maceration, hyperkeratinization, and eroded areas between the toes and on the plantar surface of the foot, as well as on other skin areas. The nails may 35 show thickening, pitting and subungal debris. Local antifungals include imidazoles, such as miconazole nitrate and clotrimazole, tolnaftate, and terbinafine hydrochloride. The common fungicidal and fungistatic chemical treatments fre- quently fail to contact the fungi in the horny layers of the skin, which means athlete’s foot slowly clears with local antifung al therapy or systemic antifungals. This requires the infected individual to take treatments for considerable lengths of time, potentially for months. Common treatments for athlete’s foot using local antifungals require treatment two or three times 40 a day for at least 7 to 14 days, and for some medications, for up to four weeks. It is common treatment to apply the topical antifungal for two weeks after the skin is healed, to eradicate all remaining fungal spores. Physicians commonly prescribe medications in the form of powders, aerosols, liquids or creams for the treatment of tinea pedis. [0007] However, reoccurrences of the infection are frequent. For some patients, such as those also afflicted with diabetes or circulatory problems, tinea infections and their treatment can be quite serious. The source of the affliction 45 often is a public safety and health concern, as the occurrence of tinea pedis is higher in public areas such as locker rooms, public showers, sports facilities, and the like. [0008] Increasingly, herbal remedies are sought due to concerns caused by antibiotic-resistant and other drug-resistant infectious agents. Even with herbal treatments, however, numerous difficulties are encountered in the treatment of medical conditions. A single herb may contain numerous active, and sometimes conflicting, components. The common 50 herb, rhubarb, for example, may be used in small doses for treating constipation due to its tannic acid component, but is a potent laxative in larger doses because of other components. Other herbs, such as black walnut extract, which may be used to treat athlete’s foot and related fungal infections, can be toxic if taken inappropriately. In addition to those difficulties mentioned in connection with single herbs, combinations raise the possibility of deleterious effects among components in the various herbs, and increase the difficulties associated with anticipating and analyzing side effects. 55 WO 96/37210 discloses various preparations in which, among others, Origanum vulgaris oil in concentrations of from 3 to 5 or 6 % and Mentha piperita oil in concentrations of from 0.5 to 1.5 % are present. These preparations comprise at least 80% of a vehicle. 2 EP 2 451 468 B1 BRIEF SUMMARY OF THE INVENTION [0009] The present invention relates to an antimicrobial composition comprising at least 40 % of one or more phenolic compounds selected from carvacrol and thymol and at least 15 % menthol. 5 [0010] In an embodiment of the present invention, the one or more phenolic compounds are contained in origanum oil. [0011] The composition comprises one or more phenolic compounds, namely carvacrol or thymol, and a secondary alcohol, namely menthol. The composition comprises at least 40% of the one or more phenolic compounds. [0012] -The composition may comprise at most about 15%, or 20% of the secondary alcohol. [0013] -The composition may further comprises an additional antifungal agent selected from the group consisting of 10 miconazole, econazole, ketoconazole, itraconazole, fluconazole, bifoconazole, terconazole, butoconazole, tioconazole, oxiconazole, sulconazole, saperconazole, clotrimazole, isoconazole, butoconazole, clioquinol, lanoconazole, neticona- zole, ciclopirox, butenafine, undecylenic acid, haloprogin, tolnaftate, nystatin, ciclopirox olamine, terbinafine, amorolfine,

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