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THI TOETATUTUMUTUALNIHUS009962372B2 (12 ) United States Patent ( 10 ) Patent No THI TOETATUTUMUTUALNIHUS009962372B2 (12 ) United States Patent ( 10 ) Patent No. : US 9 , 962, 372 B2 Milanese et al. (45 ) Date of Patent: May 8 , 2018 ( 54 ) PHARMACEUTICAL COMPOSITION FOR ( 56 ) References Cited THE TREATMENT OF MYCOSIS U . S . PATENT DOCUMENTS (71 ) Applicant: AZIENDE CHIMICHE RIUNITE 2004 / 0180965 A1 * 9/ 2004 Borgman . .. .. A61K 9 /0034 ANGELINI FRANCESCO A . C . R . A . F . 514 /649 S . p . A ., Rome ( IT ) 2009/ 0208558 AL 8 / 2009 Noe et al . ( 72 ) Inventors : Claudio Milanese , Rome ( IT ) ; FOREIGN PATENT DOCUMENTS Alessandra Capezzone De Joannon , Rome ( IT ) ; Serena Tongiani, Genzano WO 96 / 26724 AL 9 / 1996 di Roma (IT ) ; Luca Donati , Porto San Giorgio ( IT ) OTHER PUBLICATIONS Rani et al. Mini- reviews in Medicinal chemistry, 2013 , 13 ( 11) , @( 73 ) Assignee : AZIENDE CHIMICHE RIUNITE 1626 - 1655 (abstract ) .* ANGELINI FRANCESCO A . C . R . A . F . Yucesoy et al. , “ In -vitro Synergistic Effect of Fluconazole with S . p . A . , Rome (IT ) Nonsteroidal Anti - Inflammatory Agents Against Candida albicans Strains” , Journal of Chemotherapy, vol. 12 , No . 5 , 2000 , p . 385 - 389 , XP 002429141 . @( * ) Notice : Subject to any disclaimer, the term of this Boselli et al . , “ Efficacy and Tolerability of Fitostimoline ( Vaginal patent is extended or adjusted under 35 Cream , Ovules , and Vaginal Washing ) and of Benzydamine Hydro U . S . C . 154 (b ) by 0 days . days . chloride ( Tantum Rosa Vaginal Cream and Vaginal Washing ) in the Topical Treatment of Symptoms of Bacterial Vaginosis ” , ISRN Obstetrics and Gynecology, vol. 2012 , 2012 , p . 1 - 5 . (21 ) Appl . No. : 15 /541 , 245 EUCAST, “ EUCAST Definitive Document EDef 7 . 1 : method for @I the determination of broth dilution MICs of antifungal agents for ( 22 ) PCT Filed : Jan . 8 , 2016 fermentative yeasts ” , Clinical Microbiology and Infection , vol. 14 , No . 4 , Apr. 2008 , 8 pages. Franz , “ Percutaneous Absorption . On the Relevance of In Vitro ( 86 ) PCT No. : PCT/ EP2016 / 050272 Data ” , The Journal of Investigative Dermatology, vol. 64 . No. 3 , $ 371 ( c ) ( 1 ), 1975 , p . 190 - 195 . Meletiadis et al ., “ Defining Fractional Inhibitory Concentration ( 2 ) Date : Jun . 30 , 2017 Index Cutoffs for Additive Interactions Based on Self - Drug Addi tive Combinations, Monte Carlo Simulation Analysis , and In Vitro ( 87 ) PCT Pub . No . : WO2016 / 113194 In Vivo Correlation Data for Antifungal Drug Combinations against Aspergillus fumigatus" , Antimicrobial Agents and Chemotherapy , PCT Pub . Date : Jul. 21, 2016 vol. 54 . No. 2 , 2010 , 9 pages . International Search Report dated Mar . 2 , 2016 , in PCT/ EP2016 / (65 ) Prior Publication Data 050272 , filed Jan . 8 , 2016 . (65 ) Rani et al ., “ Imidazoles as Potential Antifungal Agents : A Review ” , US 2018 / 0000783 A1 Jan . 4 , 2018 Mini - Reviews in Medicinal Chemistry, vol. 13 , 2013 , p . 1626 - 1655 , XP 9183599A . Foreign Application Priority Data Moody et al ., “ In Vitro Activities of Miconazole , Miconazole ( 30) Nitrate, and Ketoconazole Alone and Combined with Rifampin Against Candida spp . And Torulopsis glabrata Recovered from Jan . 13 , 2015 ( EP ) . .. .. 15150904 Cancer Patients " . Antimicrobial Agents and Chemotherapy, vol. 17 , No. 5 , May 1980 , p . 871 -875 , XP 55180997A . (51 ) Int . Ci. Stelmachow et al ., “ Efficacy and tolerance of benzydamine in the A61K 31 /416 ( 2006 .01 ) treatment of vaginal infections " , Medical Science Monitor , vol. 4 , A61K 9 / 06 ( 2006 .01 ) No . 6 , 1998, p . 1040 - 1042 , XP 009183593. A61K 314196 ( 2006 .01 ) A61K 31 /4174 ( 2006 .01 ) * cited by examiner (52 ) U . S . CI. Primary Examiner — Yevgeny Valenrod CPC . .. .. .. .. A61K 31/ 416 ( 2013 .01 ) ; A61K 9 / 06 (74 ) Attorney, Agent, or Firm — Oblon , McClelland , ( 2013 .01 ) ; A61K 31 /4174 ( 2013 . 01 ) ; A61K Maier & Neustadt, L . L . P . 31/ 4196 (2013 .01 ) (57 ) ABSTRACT (58 ) Field of Classification Search The present invention relates to a pharmaceutical composi CPC . A61K 31/ 416 ; A61K 9 / 06 ; A61K 31 /4174 ; tion comprising a combination of benzydamine and an A61K 31 / 4196 antimycotic active ingredient, said combination having a USPC .. .. 514/ 383 synergistic effect in the treatment of mycosis . See application file for complete search history . 16 Claims, 1 Drawing Sheet U . S . Patent May 8 , 2018 US 9 , 962 ,372 B2 Fig . 1 1 % 01946 . 5 % son0 . 25 % os0 . 125 % como0 . 06 % come0 .03 % Cream A Cream B Cream C Fig . 2 9 .0x1097 Cream A 1909 www.mg wwwwwwww. Cream B 8. 0x1007 7 . 0x1007 6 .0x1007 DensitometryArbitraryUnits 5 .0x1007 Gm 4 .0x1007 .wcomwww 3 .0x1007 2 . 0x1007 . 1. 0x1007 . 0 . 0 wwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwww 0 .031 0 .062 0. 125 0. 250 0. 500 1. 000 % cream dilution US 9 , 962 , 372 B2 PHARMACEUTICAL COMPOSITION FOR organisms are affected by multiple pathways . These path THE TREATMENT OF MYCOSIS ways are often not known, and even when they are, the ways in which the pathways interact to produce the biological end FIELD OF THE INVENTION effect are often unknown . an The present invention relates to a pharmaceutical com SUMMARY OF THE INVENTION position comprising a combination of benzydamine and an antimycotic active ingredient, said combination having a The Applicant faced the problem to provide a pharma synergistic effect in the treatment of mycosis . ceutical composition for the treatment of mycosis , having an 10 improved activity when compared to the compositions BACKGROUND OF THE INVENTION known in the art . Fungi belonging to the genus Candida are one of the most The Applicant has found that benzydamine can be used in common causes of fungal infections worldwide . association with antimycotic active ingredients derived from Many species of Candida are harmless commensals or 15 imidazole . endosymbionts of their hosts , such as for example human In particular , the Applicant has now surprisingly found beings . that the combination of benzydamine with an antimycotic Fungi belonging to the species Candida albicans and active .ingredient derived from imidazole has a synergistic Candida tropicalis are normally present on the mucosa of effect in inhibiting the growth of fungi belonging to genus oral cavity , gastro - intestinal tract and vagina . However, 20 Candida . when the flora of the mucosae is altered , for example due to Thus, in a first aspect, the present invention relates to a long treatment with antibiotics or hormonal changes , fungi pharmaceutical composition comprising a combination of can abnormally multiply and cause superficial infections, for benzydamine and an imidazole -antimycotic or a salt thereof , example in the mouth or in the vagina ,known as candidiasis . and at least one pharmaceutically acceptable excipient, for In immunosuppressed people , fungi can even cause severe 25 use in the treatment of Candida mycosis . systemic infections, known as candidemia , that are some- Advantageously , benzydamine in the composition accord times deadly . ing to the present invention gives relief from vulvovaginal Vulvovaginitis caused by fungi represents today about 1115itching and pain . 30 - 35 % of vaginal infections and is mostly caused by Preferably , said imidazole -antimycotic is selected in the Candida albicans fungi. Vulvovaginitis is accompanied by changes of the vaginal 30 group comprising bifonazole , butoconazole , chlormidazole , pH and the main symptoms are intense vaginal and /or vulvar clotrimazole , croconazole, econazole , fenticonazole , keto itching , leakages , inflammation and pain . conazole , isoconazole , miconazole , neticonazole , omocon Typically , the treatment is by administration of topical azole , oxiconazole , sertaconazole , sulconazole , tioconazole antimycotic drugs in form of creams, vaginal ovules and 35 or salts thereof. solutions for external use. In case of severe and / or relapsing More preferably, said imidazole -antimycotic is selected in infections , antimycotic drugs are administered orally . the group comprising bifonazole , butoconazole , clotrima PevarylTM is a commercially available cream for the zole , econazole , fenticonazole , ketoconazole , isoconazole , treatment of vulvovaginal mycosis , containing 1 % w / w of miconazole , omoconazole , sertaconazole , sulconazole , tio econazole nitrate . 40 conazole or salts thereof. Econazole is an imidazole derivative , endowed with a Even more preferably , said imidazole - antimycotic is broad spectrum antimycotic activity and commonly used for selected in the group comprising butoconazole , econazole , the treatment of Candida albicans mycosis . fenticonazole , isoconazole , miconazole , sulconazole or salts Several patent applications disclose combinations of thereof . active ingredients useful in the treatment of oral and vul- 45 Advantageously , said imidazole -antimycotic is econ vovaginal mycosis . azole , miconazole or a salt thereof . WO 96 /26724 discloses a pharmaceutical composition Preferably , said Candida mycosis is caused by Candida comprising an anti - inflammatory amount of benzydamine or Albicans, Candida lusitaniae , Candida tropicalis , Candida a salt thereof, an antimicrobially effective amount of an glabrata , Candida . rugosa , Candida parapsilosis, Candida antimicrobial agent and a pharmaceutically acceptable car - 50 tropicalis , or Candida dubliniensis . More preferably , said rier or excipient. Candida mycosis is caused by Candida Albicans, Candida US 2009 / 0208558 relates to the use of an antimycotic lusitaniae
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