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Therapeutic Anti-Fungal Nail Preparation Therapeutische Antifungale Zubereitung Für Nägel Preparation Antifongique Therapeutique Pour Ongles

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Therapeutic Anti-Fungal Nail Preparation Therapeutische Antifungale Zubereitung Für Nägel Preparation Antifongique Therapeutique Pour Ongles Europäisches Patentamt *EP001130964B1* (19) European Patent Office Office européen des brevets (11) EP 1 130 964 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.7: A61P 31/10, A61K 31/20, of the grant of the patent: A61K 31/22, A61K 31/27, 09.11.2005 Bulletin 2005/45 A61K 31/415, A61K 31/44, (21) Application number: 99960362.4 A61K 31/47, A61K 31/495, A61K 31/505, A61K 31/71, (22) Date of filing: 15.11.1999 A61K 47/10, A61K 47/20 (86) International application number: PCT/US1999/027053 (87) International publication number: WO 2000/028821 (25.05.2000 Gazette 2000/21) (54) THERAPEUTIC ANTI-FUNGAL NAIL PREPARATION THERAPEUTISCHE ANTIFUNGALE ZUBEREITUNG FÜR NÄGEL PREPARATION ANTIFONGIQUE THERAPEUTIQUE POUR ONGLES (84) Designated Contracting States: (56) References cited: AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU EP-A- 0 270 316 WO-A-93/11734 MC NL PT SE US-A- 5 612 324 US-A- 5 767 161 US-A- 5 814 305 (30) Priority: 16.11.1998 US 193073 • SCOTT E M ET AL: "Demonstration of synergy (43) Date of publication of application: with fluconazole and either ibuprofen, sodium 12.09.2001 Bulletin 2001/37 salicylate, or propylparaben against Candida albicans in vitro." ANTIMICROBIAL AGENTS (73) Proprietor: Astan, Inc. AND CHEMOTHERAPY, (1995 DEC) 39 (12) Birmingham, AL 35242 (US) 2610-4. , XP002196358 • TARIQ V N ET AL: "Use of decimal assay for (72) Inventor: REEVES, Stanley, Forrest additivity to demonstrate synergy in pair Demopolis, AL 36723 (US) combinations of econazole, nikkomycin Z, and ibuprofen against Candida albicans in vitro." (74) Representative: Elsy, David et al ANTIMICROBIAL AGENTS AND Withers & Rogers LLP CHEMOTHERAPY, (1995 DEC) 39 (12) 2615-9. , Goldings House, XP002196359 2 Hays Lane • SANYAL ET AL.: LETTERS IN APPLIED London SE1 2HW (GB) MICROBIOLOGY, vol. 17, 1993, pages 109-111, XP001057670 • STUETTGEN G ET AL: "BIO AVAILABILITY SKIN PENETRATION AND NAIL PENETRATION OF TOPICALLY APPLIED ANTI MYCOTICS" MYKOSEN, vol. 25, no. 2, 1982, pages 74-80, XP001068847 ISSN: 0027-5557 Note: Within nine months from the publication of the mention of the grant of the European patent, any person may give notice to the European Patent Office of opposition to the European patent granted. Notice of opposition shall be filed in a written reasoned statement. It shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 1 130 964 B1 Printed by Jouve, 75001 PARIS (FR) 1 EP 1 130 964 B1 2 Description months) application of topical fungicidal creams and/or solutions in combination with systemic fungal treatment Technical Field drugs such as griseofulvin, terbinafine, and itracona- zole. US 5814305 discloses that hydrophilic penetration [0001] The present invention relates generally to ther- 5 agents improve the penetration of antifungal agents apeutic preparations using the combination of ibuprofen through the nails. Some of the systemic treatments have and dimethyl sulfoxide ("DMSO") as a transport mech- undesirable side effects such as nausea, headache, anism to deliver active agents to infected areas. In par- photosensitivity, gastrointestinal intolerance, elevated ticular, the present invention relates to therapeutic prep- liver enzymes, and undesirable drug interactions, mak- arations using the combination of ibuprofen and DMSO 10 ing the process of eradication difficult and troublesome. to deliver anti-fungal agents to infected areas relatively [0006] It is also noted that systemic fungal treatments inaccessible to conventional therapeutic compounds. are expensive. A treatment program using terbinafine tablets (250mg) can cost over $600.00 and a therapy Background Art using itraconazole can cost between $600.00 and 15 $1200.00. Conversely, the instant invention contem- [0002] Infections on the exterior of the human body plates a non-systemic treatment program costing under are caused by a variety of micro-organisms, including $50.00. bacteria, fungi, and molds. Many micro-organisms living [0007] Part of the difficulty of quickly curing Ony- on or within the body are beneficial, but others multiply chomycosis is the inability to deliver effective anti-fungal rapidly and may form infections if left untreated. Some 20 agents to the pathogenically active areas such that all organisms such as microscopic plants or fungi can live of the pathogenic fungus is eradicated. Without full erad- on the skin and obtain nourishment from dead tissues ication, reoccurrence is likely necessitating a new cycle such as hair, nails, and outer skin layers. When fungi of combined topical and/or systemic treatments, with the growing on the body grows out of control, an infection aforementioned systemic effects. Treatment is compli- can result with detrimental effects to living tissue. In ad- 25 cated by the fact that the cutaneous nail shell is not eas- dition, fungal infections are communicable and individ- ily penetrated and treatments of infected areas often re- uals who frequent swimming pools, gyms, shower quire thinning of the nail to allow better penetration of rooms, and other humid and/or wet environments are anti-fungal agents. The nail acts as a protective barrier susceptible to being infected with various types of fungal under which fungus can grow unhindered and even acts infections as other infected individuals visit these public 30 as a vessel for spreading the disease. Current topical areas. anti-fungal ointments and solutions used to treat Ony- [0003] One class of external fungi is Onychomycosis, chomycosis do not penetrate in to nail bed easily and commonly referred to as "nail fungus." Onychomycosis tend to leave some portion of the fungus alive after treat- is an infection of the nail (i.e. unguis) and nail bed ment causing reoccurrence of the disease. Heretofore, caused by pathogenic fungi, among other micro-organ- 35 the medical industry has not produced a topical treat- isms, and while not life threatening the disease can ment having the necessary chemical properties to effec- cause chronic discomfort and embarrassment. The dis- tively pass through the hard cutaneous nail shell and ease attacks the nails and their growth centers making penetrate into the Nail bed for rapid and complete de- them appear cracked, yellow, and highly disfigured. In struction of the fungal infection. acute cases, Onychomycosis can cause the nail to be- 40 [0008] Therefore, there is a need for a topical solution come thick and yellow in color, making it vulnerable to that quickly and thoroughly penetrates the nail shell, un- easy damage and from which subungual hemorrhages derlying nail bed, and surrounding nail tissue to deliver can result. an effective anti-fungal agent that will kill the causes of [0004] Onychomycosis is caused by a variety of mi- Onychomycosis. cro-organisms such as dermatophytes, yeast, and 45 molds. However, the majority of Onychomycosis cases Disclosure of Invention are caused by fungi such as Trichophyton rubrum, Tri- chophyton mentagrophytes, Trichophyton tonsurans, [0009] It is the object of the present invention to pro- and Epidermophyton floccosum. Once these micro-or- vide a topical solution containing effective antifungal ganisms establish subcutaneous growth, eradication 50 agents that will penetrate the hard cutaneous shell to kill with current over the counter treatment is difficult and the cause of Onychomycosis. reoccurrences of the disease can be costly and time [0010] A further object of the present invention is to consuming. provide a method of making the penetrating topical so- [0005] In recent years Onychomycosis has spread to lution. a higher percentage of adults due, in part, to its conta- 55 [0011] An even further object of the present invention gious nature and the lack of effective medications that is to provide the use of the topical solution according to can quickly cure the disease once established within the the present invention for the manufacture of a medica- nail bed. Current treatments include long term (3-9 ment, for a therapeutic treatment procedure for curing 2 3 EP 1 130 964 B1 4 Onychomycosis without the advent of systemic drugs. c. from 10 to 80% by volume of a polyglycol base [0012] In summary, the invention provides a combina- into which said agent and said ibuprofen are dis- tion of an anti-fungal agent with combination of ibupro- solved; and fen and DMSO in an anhydrous solution of polyglycol. d. from 10 to 80% solution DMSO mixed with said [0013] The invention provides a topical solution effec- 5 polyglycol base and in an inverse proportion by vol- tive in inhibiting the growth of micro-organisms causing ume with said polyglycol base. Onychomycosis, consisting essentially of: And: a. an antifungal agent for killing micro-organisms [0017] A topical solution according to the invention, causing Onychomycosis; 10 consisting essentially of: b. ibuprofen; c. a polyglycol base into which said agent and said a. an antifungal agent selected from Miconazole, ibuprofen are dissolved; and Clotrimazole, Tioconazole, Nystatin, Terconazole, d. a solution of DMSO mixed with said polyglycol Butoconazole Nitrate, Unecylenic Acid, Clioquinol, base. 15 Ciclopirox Olamine, Econazole Nitrate, Triacetin, Tolnaftate, Flucytosine, and Ketoconazole; [0014] The invention also provides b. ibuprofen; a pharmaceutical composition for enhancing pen- c. a polyglycol base into which said agent and said etration of a pharmaceutically active antifungal sub- ibuprofen are dissolved; and stance, comprising a topical solution according to the 20 d. a solution of DMSO mixture with said polyglycol invention, consisting essentially of: base for use in the manufacture of a medicament to treat nail fungus. a. an antifungal agent selected from Miconazol, Clotrimazole, Tioconazole, Nystatin, Terconazole, [0018] The combination of Butoconazole Nitrate, Unecylenic Acid, Clioquinol, 25 ibuprofen and DMSO acts as a delivery vehicle so Ciclopirox Olamine, Econazole Nitrate, Triacetin, that active anti-fungal agents such as Miconazole, can Tolnaftate, Flucytosine, and Ketoconazole; be delivered directly to fungal infected areas under and b.
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