JP6653342B2 - 真菌感染症の治療用の局所用オイル組成物 - Google Patents
真菌感染症の治療用の局所用オイル組成物 Download PDFInfo
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- JP6653342B2 JP6653342B2 JP2018038329A JP2018038329A JP6653342B2 JP 6653342 B2 JP6653342 B2 JP 6653342B2 JP 2018038329 A JP2018038329 A JP 2018038329A JP 2018038329 A JP2018038329 A JP 2018038329A JP 6653342 B2 JP6653342 B2 JP 6653342B2
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Description
本発明は、真菌感染症の治療用の、抗真菌剤、オイル、および賦形剤または添加剤を含む局所用組成物を提供する。本発明は、局所真菌感染症の治療用の、C-10を超える脂肪酸またはそれらのエステルを含まない組成物をさらに提供する。本発明は、抗真菌剤、C11未満の鎖長を有する脂肪酸もしくはそのエステル、および賦形剤または添加剤を含む抗真菌組成物をさらに提供する。
皮膚の真菌感染症は「真菌症」としても公知である。それらは一般的であり、通常、軽症である。しかし、病気であるかまたはそうでなければ免疫力が低下した人においては、真菌は、時々、重篤な疾患を引き起こし得る。ヒトにおける真菌感染症は、表在性、即ち、皮膚表面から、深部浸潤型または播種性感染症の範囲に及ぶ。
本発明の主目的は、真菌感染症の治療用の、抗真菌剤、オイル、および賦形剤または添加剤を含む抗真菌組成物を提供することである。本発明のさらに別の目的は、局所真菌感染症の治療用の、C-10を超える脂肪酸またはそれらのエステルを含まない抗真菌組成物を提供することである。
本発明は、C-11以上の脂肪酸およびそれらのエステルを含まない抗真菌組成物を提供し、何故ならばこれらの脂肪酸/エステルは真菌の増殖のための栄養素として役立つためである。本発明はさらに、頭皮上の既存のフケを除去する、またはフケ発生の再発を防止もしくは低減する、局所用抗真菌オイル組成物を提供する。本発明はさらに、抗真菌剤、C-11未満の鎖長を有する脂肪酸もしくはそのエステル、および賦形剤または添加剤を含む、抗真菌組成物を提供する。
[1]
少なくとも1つの抗真菌剤、少なくとも1つのオイル、および少なくとも1つの賦形剤を含む抗真菌組成物であって、該組成物がC-11以上の脂肪酸およびエステルを含まない、抗真菌組成物。
[2]
前記抗真菌剤を約0.01重量%〜約10重量%含む、前記[1]の抗真菌組成物。
[3]
前記抗真菌剤を約0.01重量%〜約5重量%含む、前記[2]の抗真菌組成物。
[4]
前記抗真菌剤を約0.01重量%〜約2重量%含む、前記[3]の抗真菌組成物。
[5]
前記抗真菌剤が、ピロクトンオラミン、シクロピロクスオラミン、ケトコナゾール、クリンバゾール、硝酸ミコナゾール、イトラコナゾール、フルコナゾール、エコナゾール、テルコナゾール、サペルコナゾール、アモロルフィン、オキシコナゾール、クロトリマゾール、ルリコナゾール、テルビナフィン、ブテナフィン、ナフチフィン、二硫化セレン、サリチル酸、硫黄、タール、ウンデカン酸、ジンクピリチオン、ヒノキトール、アルニカエキス、クルミ殻エキス、ティーツリー油、ローズマリー油、もしくはバーチ油、またはそれらの組み合わせである、前記[1]の抗真菌組成物。
[6]
前記抗真菌剤がジンクピリチオンである、前記[5]の抗真菌組成物。
[7]
前記抗真菌剤がピロクトンオラミンである、前記[5]の抗真菌組成物。
[8]
前記抗真菌剤がケトコナゾールである、前記[5]の抗真菌組成物。
[9]
前記抗真菌剤がティーツリー油である、前記[5]の抗真菌組成物。
[10]
前記抗真菌剤がカプリル酸またはそのエステルである、前記[5]の抗真菌組成物。
[11]
前記抗真菌剤がカプリン酸またはそのエステルである、前記[5]の抗真菌組成物。
[12]
前記抗真菌剤がピロクトンオラミンおよびケトコナゾールである、前記[5]の抗真菌組成物。
[13]
前記抗真菌剤がピロクトンオラミン、ケトコナゾール、およびジンクピリチオンである、前記[5]の抗真菌組成物。
[14]
前記抗真菌剤がピロクトンオラミンおよびカプリル酸のエステルである、前記[5]の抗真菌組成物。
[15]
前記オイルが、パラフィン油、シリコーン油、テルペン、脂肪アルコール、アジピン酸ジブチル、アジピン酸ジオクチル、C10以下の脂肪酸もしくはエステル、またはそれらの組み合わせである、前記[1]の抗真菌組成物。
[16]
前記オイルが脂肪酸である、前記[15]の抗真菌組成物。
[17]
前記オイルがパラフィン油である、前記[15]の抗真菌組成物。
[18]
前記オイルを約1重量%〜約99重量%含む、前記[1]の抗真菌組成物。
[19]
前記賦形剤が溶媒または添加剤である、前記[1]の抗真菌組成物。
[20]
前記賦形剤を約0.5重量%〜約99重量%含む、前記[19]の抗真菌組成物。
[21]
前記賦形剤が溶媒である、前記[19]の抗真菌組成物。
[22]
前記賦形剤が添加剤である、前記[19]の抗真菌組成物。
[23]
前記組成物が、クリーム、オイル、ローション、シーラム、ジェル、シャンプー、マニキュア、軟膏、フォーム、スプレーまたはエアゾールである、前記[1]の抗真菌組成物。
[24]
前記組成物がフケ防止オイルである、前記[23]の抗真菌組成物。
[25]
前記抗真菌剤が、ピロクトンオラミン、シクロピロクスオラミン、ケトコナゾール、クリンバゾール、硝酸ミコナゾール、イトラコナゾール、フルコナゾール、エコナゾール、テルコナゾール、サペルコナゾール、アモロルフィン、オキシコナゾール、クロトリマゾール、ルリコナゾール、テルビナフィン、ブテナフィン、ナフチフィン、二硫化セレン、サリチル酸、硫黄、タール、ウンデカン酸、ジンクピリチオン、ヒノキトール、アルニカエキス、クルミ殻エキス、ティーツリー油、ローズマリー油、もしくはバーチ油、またはそれらの組み合わせである、前記[24]のフケ防止オイル組成物。
[26]
前記抗真菌剤がジンクピリチオンである、前記[25]のフケ防止オイル組成物。
[27]
前記抗真菌剤がシクロピロクスオラミンである、前記[25]のフケ防止オイル組成物。
[28]
前記抗真菌剤がピロクトンオラミンである、前記[25]のフケ防止オイル組成物。
[29]
前記抗真菌剤がケトコナゾールである、前記[25]のフケ防止オイル組成物。
[30]
前記抗真菌剤がピロクトンオラミンおよびケトコナゾールである、前記[25]のフケ防止オイル組成物。
[31]
[1]の組成物を含むマニキュア組成物。
[32]
前記抗真菌剤が、ピロクトンオラミン、シクロピロクスオラミン、ケトコナゾール、イトラコナゾールまたはテルビナフィンである、前記[31]のマニキュア組成物。
[33]
少なくとも1つの抗真菌剤、C-8脂肪酸またはエステル、および少なくとも1つの賦形剤を含む、抗真菌組成物。
[34]
前記抗真菌剤がピロクトンオラミンである、前記[33]の組成物。
[35]
前記組成物が、クリーム、オイル、ローション、シーラム、ジェル、シャンプー、マニキュア、軟膏、フォーム、スプレーまたはエアゾールである、前記[33]の組成物。
表1:ピロクトンオラミン−オイル組成物
表2:ケトコナゾール−オイル組成物
表3:ピロクトンオラミンのオイル組成物についてのMICの結果
表4:ケトコナゾールのオイル組成物についてのMICの結果
表5:抗真菌剤としてピロクトンオラミンを含有するオイル組成物
表6:M.フルフルに対するピロクトンオラミンを含有するオイル組成物のMIC
表7:M.オブツサに対するピロクトンオラミンを含有するオイル組成物についてのMIC
表8:抗真菌剤としてケトコナゾールを含有するオイル組成物
表9:ピロクトンオラミンおよびケトコナゾールを組み合わせて含有するオイル組成物
表10:抗真菌剤としてのピロクトンオラミンおよびミノキシジルを含有するオイル組成物
表11:C-11以上の脂肪酸/エステルを含まない抗真菌剤を含有するゲル組成物
表12:M.フルフルに対するピロクトンオラミンを含有するゲル組成物の阻止帯
表13:抗真菌剤ピロクトンオラミンまたはケトコナゾールを含有するクリーム組成物の調製
本発明は様々な修飾物および代替形態の影響を受けやすいが、その具体的な局面を例および図面によって示し、下記において詳細に説明する。しかし、それは本発明を開示される特定の形態に限定するようには意図されず、しかしそれどころか、本発明は、添付の特許請求の範囲によって規定される本発明の精神および範囲内に入る全ての修飾物、等価物、および代替物を網羅することが理解されるべきである。
(A)少なくとも1つの抗真菌剤;
(B)少なくとも1つのオイル;および
(C)少なくとも1つの賦形剤
を含む、真菌感染症の治療用の組成物であって、
ここで、該組成物がC-11脂肪酸およびそれらのエステルを含まない、組成物に関する。
(A)少なくとも1つの抗真菌剤;
(B)少なくとも1つのC10以下の脂肪酸またはそのエステル;および
(C)少なくとも1つの賦形剤
を含む、フケ防止オイル組成物を提供することである。
(a)ピロクトンオラミン、ケトコナゾール、ジンクピリチオンまたはそれらの組み合わせからなる群より選択される抗真菌剤;ここで、該抗真菌剤は、総組成物の0.01重量%〜約10重量%の範囲内、より好ましくは0.01重量%〜5重量%の範囲内、より好ましくは0.01重量%〜2重量%の範囲内に存在する;
(b)パラフィン油、サリチル酸、カプリン酸および誘導体、カプリル酸および誘導体、C-10未満の炭素鎖長を有する脂肪酸もしくはエステル、またはそれらの組み合わせからなる群より選択されるオイル、ここで、該オイルは1 %〜99%の範囲内に存在する;
(c)低級脂肪族アルコール、低級アルキルアセテート、エーテル、C11未満の炭素鎖長を含有するカルボン酸もしくは誘導体、脂肪アルコールまたはそれらの組み合わせの群より選択される溶媒;ならびに
(d)増粘剤、抗酸化剤、香料/芳香剤、精油、pH調整剤、ハーブエキス、保存剤、ヘアコンディショニング物質、ヘアケア補助剤、スキンケア補助剤、スキンケア剤、皮膚栄養剤、皮膚軟化剤、色素、保湿剤、ビタミン、スフィンゴセリル、日焼け止め、界面活性剤、油溶性ポリマー、抗しわ剤、光もしくはダスト保護剤またはそれらの組み合わせの群より選択される添加剤。
活性な剤をエタノールまたはイソプロピルアルコール(IPA)に溶解することによって、組成物を調製した。次いで、オレイルアルコールを添加し、均質溶液が得られるまで撹拌した。流動パラフィン以外の他の賦形剤または添加剤を添加し、撹拌し、透明溶液を得た。最後に重量を流動パラフィンで調整し、均質溶液が得られるまで撹拌した。最終製剤は透明なオイル溶液であった。表1は、様々な賦形剤または添加剤を使用する、抗真菌剤としてピロクトンオラミンを含有する抗真菌透明オイル組成物を示す。
1.ピロクトンオラミンを含有する、基油として流動パラフィンを使用する組成物は、透明なオイル溶液であった。
2.他の賦形剤、例えば、ティーツリー油、シクロメチコン(D4)、酢酸トコフェロールなどの添加は、透明なオイル溶液に見える組成物としての製剤の物理的安定性に影響を与えなかった。
活性な剤をエタノールに溶解することによって、組成物を調製した。次いで、オレイルアルコールを添加し、均質溶液が得られるまで撹拌した。流動パラフィン以外の他の賦形剤または添加剤を添加し、撹拌し、透明溶液を得た。最後に重量を流動パラフィンで調整し、均質溶液が得られるまで撹拌した。最終製剤は透明なオイル溶液であった。表2は、様々な賦形剤または添加剤を使用する、抗真菌剤としてケトコナゾールを含有する抗真菌透明オイル組成物を示す。
1.ケトコナゾールを含有する、基油として流動パラフィンを使用する組成物は、透明なオイル溶液であった。
2.他の賦形剤、例えば、ティーツリー油、テルペン-4-オール、カプリル酸、シクロメチコン(D4)などの添加は、製剤の物理的安定性に影響を与えず、組成物は透明なオイル溶液のように見えた。
マラセチア種は、ある条件下で病原性であり得る皮膚の片利共生生物として認識されている、親油性で単極性の酵母である(Indian Journal of Medical Microbiology, (2004) 22 (3):179-181)。フケ/脂漏性皮膚炎と最も密接に関連している真菌の脂質要件を比較するために、最も良く研究されるマラセチア種はM.フルフルである。脂質同化インビトロアッセイを設計し、M.フルフル(MTCC 1374)の増殖に対する脂質効果を調べた。
1.結果は、6日間までに、インビトロ条件において脂肪酸/エステルまたはオイルの非存在下でM.フルフルの増殖がなかったことを示した(図1)。
2.脂肪酸またはエステル、例えば、リノール酸、オレイン酸、ラウリン酸、パルミチン酸、オレイン酸エチル、ミリスチン酸イソプロピル、および脂肪酸/エステルを含有するオイル、例えば、ヤシ油、カラシ油などを含有した培養培地は、6日間までに、真菌のコンフルエントな増殖を示した。
3.低級炭素脂肪酸(C≦10)、例えば、カプリル酸(C8)およびカプリン酸(C10)を含む培養培地は、真菌の増殖についての栄養素を提供せず、6日間までに、増殖は観察されなかった。
最小発育阻止濃度(MIC)は、抗真菌効能を示すための指標と考えられる。従って、組成物のMICの値が低いほど、その抗真菌効能はよりよい。
1.異なる溶媒、それぞれ、イソプロピルアルコール、オレイルアルコール、およびエタノールを含む、ピロクトンオラミン含有オイル組成物VPO-018、VPO-022、およびVPO-028は32μg/mlのMICを示し、これは陽性対照のMICと同様であった。ここで、薬物は表3に示されるのと同一の濃度でDMSO中に溶解されている。
他の添加剤、例えば、カプリル酸、シクロメチコン(D4)、酢酸トコフェロールなどの添加は、表1に示す濃度で使用した場合、オイル組成物のMICに影響を与えなかった。
方法:マラセチア・フルフル(MTCC 1374)に対するケトコナゾールを含有する、オイル組成物のいくつかのインビトロ活性を、寒天希釈法によって測定した。抗真菌組成物の適切な希釈物を、融解したLeeming Notman培地へ添加した。平板培地が凝固した後、適切なcfu/mlに調節されたM.フルフル接種物を寒天平板培地上に画線し、6日間インキュベートした。インキュベーション後、目に見えるM.フルフル増殖について第3日および第6日に平板培地を観察した。MICは、真菌を増殖させない、抗真菌活性物の最小試験希釈と定義される。
1.ケトコナゾール含有オイル組成物は0.25μg/mlのMICを示し、これは陽性対照のMICと同様であった。ここで、薬物は表4に示されるのと同一の濃度でDMSO中に溶解されている。
A)インビトロ条件下でのM.フルフルの増殖についてのグリセロールまたはグリコールエステル(炭素数C-11未満)である様々なオイルの研究
マラセチア種は、ある条件下で病原性であり得る皮膚の片利共生生物として認識されている、親油性で単極性の酵母である。フケ/脂漏性皮膚炎と最も密接に関連している真菌の脂質要件を比較するために、最も良く研究されるマラセチア種はM.フルフルである。脂質同化インビトロアッセイを設計し、M.フルフル(MTCC 1374)の増殖に対するC-11未満の脂肪酸またはそれらのエステルの脂質効果を調べた。
脂質同化インビトロアッセイを設計し、M.フルフル(MTCC 1374)の増殖に対するC-10超の脂肪酸またはそれらのエステルの脂質効果を調べた。サブローデキストロース含有低融点寒天を融解し、38℃へ冷却した。真菌の増殖を研究するために、脂肪酸/エステル成分、例えば、脂肪酸またはエステル、例えば、ラウリン酸、パルミチン酸、ミリスチン酸、オレイン酸、リノール酸、ミリスチン酸イソプロピル、オレイン酸エチル、カラシ油、ヤシ油を、種々の濃度で添加した。2%オリーブ油を含む陽性対照、および脂肪物質を含まない陰性対照も維持した。凝固後、無菌的に、適切なcfu/mlに調節されたM.フルフル接種物を寒天平板培地に画線した。
A)抗真菌剤としてピロクトンオラミンを含有する、C-11以上の脂肪酸/エステルを含まないオイル組成物の調製
活性な剤をエタノールまたは他の適切な溶媒に溶解することによって、これらの組成物を調製した。次いで、オレイルアルコールを添加し、均質溶液が得られるまで撹拌した。流動パラフィン以外の他の賦形剤または添加剤を添加し、撹拌し、透明溶液を得た。最後に総体積を流動パラフィンで調整し、均質溶液が得られるまで撹拌した。最終製剤は透明なオイル溶液であり、表5に与えるように1P、2P、3Pおよび4Pとコード化した。組成物は全て透明溶液である。組成物1Pおよび2Pにおいて、カプリル酸を添加し、製剤のpHのバランスを取った。
表6および表7に示されるように、C-11以上の脂肪酸またはそれらのエステルを含まない、ピロクトンオラミンを含有するオイル組成物は、M.フルフルに対して16〜32μg/mlの範囲およびM.オブツサ(M.obtusa)に対して8〜16μg/mlの範囲のMICを示した。5%ヒマワリ油および10%オレイン酸と共に同様の量のピロクトンオラミンを含有する組成物は、両方の株に対して64μg/mlのMICを示した。これらの結果は、C-10を超えるトリグリセリド/遊離脂肪酸に富む植物油(ヒマワリ)の存在が、抗真菌剤の活性に対して悪影響を有することを示している。同様に、C-10を超える脂肪酸(例えば、オレイン酸)の存在も、抗真菌剤の活性に対して悪影響を有する。
活性な剤をエタノールまたは他の適切な溶媒に溶解することによって、これらの組成物を調製した。次いで、オレイルアルコールを添加し、均質溶液が得られるまで撹拌した。流動パラフィン以外の他の賦形剤または添加剤を添加し、撹拌し、透明溶液を得た。最後に総体積を流動パラフィンで調整し、均質溶液が得られるまで撹拌した。最終製剤は透明なオイル溶液であり、表8に与えるように、1K、2Kとコード化した。組成物は全て透明溶液である。
活性な剤をエタノールまたは他の適切な溶媒に溶解することによって、これらの組成物を調製した。次いで、オレイルアルコールを添加し、均質溶液が得られるまで撹拌した。流動パラフィン以外の他の賦形剤または添加剤を添加し、撹拌し、透明溶液を得た。最後に総体積を流動パラフィンで調整し、均質溶液が得られるまで撹拌した。最終製剤は透明なオイル溶液であり、表9に与えるように、1PK、2PKとコード化した。
組成物を上述のように調製し、表10に与えるように、1PM、2PMおよび3PMとコード化した。
A)異なる抗真菌剤を含有する、C-11以上の脂肪酸/エステルを含まない様々なゲル組成物の調製
最初に、カーボポールを水へ添加し、24時間膨潤させた。フケ防止剤を最小量の溶媒に溶解し、カーボポールベースへ添加し、続いて、トリエタノールアミンまたは水酸化ナトリウムの希釈水溶液で中和し、pH 5.0〜7.0を得た。ゲル組成物を表11に示すように1G、2G、3G、4G、5Gおよび6Gとコード化した。
ゲル組成物の効能を研究するために、ZOIを寒天ウェル拡散(Agar Well Diffusion)法によって測定した。観察を表12に示した。
表12に示されるように、ピロクトンオラミンを含有するゲル組成物(1G)は、M.フルフルに対して1.2〜0.9 cmの範囲のZOI(阻止帯)を示した。一方、4%プロピレングリコールモノカプリレートと共に同様の量のピロクトンオラミンを含有する組成物(2G)は、M.フルフルに対してZOI 1.5〜1.3 cmを示した。ベース製剤1Gに10 %オレイン酸を含めると、阻止帯は観察されなかった。これらの結果は、C-10を超える遊離脂肪酸であるオレイン酸の存在は抗真菌剤の活性に対して悪影響を有することを示した。
クリームを溶融法によって調製し、ここで、全ての油溶性成分を計量し、60〜80℃の温度で融解させた。水相を同一の温度で維持し、絶えず撹拌しながら油相を水相へ注ぎ、続いて適度に撹拌しながら徐冷した。クリーム組成物を表13に示すように1C、2C、3C、4Cとコード化した。
C−透明、ST−僅かに濁っている、PO−ピロクトンオラミン、IPA−イソプロピルアルコール、OA−オレイルアルコール、Cap.A−カプリル酸、Toco.Ace.−酢酸トコフェロール、TTO−ティーツリー油、LLP−軽質流動パラフィン、App−外観
Claims (18)
- 少なくとも1つの抗真菌剤、少なくとも1つのオイル、および少なくとも1つの賦形剤を含む抗真菌組成物であって、前記組成物がC-11以上の脂肪酸およびエステルを含まず、ならびに前記少なくとも1つの抗真菌剤、および少なくとも1つのオイルが、それぞれ以下の(i)または(ii)である、前記抗真菌組成物:
(i)前記少なくとも1つの抗真菌剤が、テルビナフィン、ブテナフィン、クロトリマゾール、ケトコナゾール、ジンクピリチオン、ルリコナゾール、ピロクトンオラミン、エフィナコナゾール、およびシクロピロクスオラミンからなる群より選択され、かつ前記少なくとも1つのオイルが、プロピレングリコールのモノカプリレート、またはグリセリルモノカプリレートである;
(ii)前記少なくとも1つの抗真菌剤が、ブテナフィン、クロトリマゾール、ケトコナゾール、ルリコナゾール、ピロクトンオラミン、エフィナコナゾール、シクロピロクスオラミン、およびイトラコナゾールからなる群より選択され、かつ前記少なくとも1つのオイルが、カプリル酸である。 - 前記抗真菌剤を約0.01重量%〜約10重量%含む、請求項1記載の抗真菌組成物。
- 前記抗真菌剤を約0.01重量%〜約5重量%含む、請求項2記載の抗真菌組成物。
- 前記抗真菌剤を約0.01重量%〜約2重量%含む、請求項3記載の抗真菌組成物。
- (i)前記少なくとも1つの抗真菌剤が、ピロクトンオラミン、ケトコナゾール、クロトリマゾール、テルビナフィン、またはジンクピリチオンであり、かつ前記少なくとも1つのオイルが、プロピレングリコールのモノカプリレート、またはグリセリルモノカプリレートであり;
あるいは
(ii)前記少なくとも1つの抗真菌剤が、ピロクトンオラミン、ケトコナゾール、クロトリマゾール、イトラコナゾール、ルリコナゾール、またはジンクピリチオンであり、かつ前記少なくとも1つのオイルが、カプリル酸である、
請求項1記載の抗真菌組成物。 - 前記抗真菌剤がジンクピリチオンである、請求項5記載の抗真菌組成物。
- 前記抗真菌剤がピロクトンオラミンである、請求項5記載の抗真菌組成物。
- 前記抗真菌剤がケトコナゾールである、請求項5記載の抗真菌組成物。
- 前記抗真菌剤がピロクトンオラミンおよびケトコナゾールである、請求項5記載の抗真菌組成物。
- 前記抗真菌剤がピロクトンオラミン、ケトコナゾール、およびジンクピリチオンである、請求項5記載の抗真菌組成物。
- 前記オイルを約1重量%〜約99重量%含む、請求項1記載の抗真菌組成物。
- 前記賦形剤が溶媒または添加剤である、請求項1記載の抗真菌組成物。
- 前記賦形剤を約0.5重量%〜約99重量%含む、請求項12記載の抗真菌組成物。
- 前記賦形剤が溶媒である、請求項12記載の抗真菌組成物。
- 前記賦形剤が添加剤である、請求項12記載の抗真菌組成物。
- 前記組成物が、クリーム、オイル、ローション、シーラム、ジェル、シャンプー、マニキュア、軟膏、フォーム、スプレーまたはエアゾールである、請求項1記載の抗真菌組成物。
- 前記組成物がフケ防止オイルである、請求項16記載の抗真菌組成物。
- 前記組成物が、マニキュアである、請求項16記載の抗真菌組成物。
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US20140364440A1 (en) | 2014-12-11 |
JP2015500871A (ja) | 2015-01-08 |
HK1203361A1 (en) | 2015-10-30 |
IL233247A0 (en) | 2014-08-31 |
JP6339940B2 (ja) | 2018-06-06 |
EP2793833B1 (en) | 2020-06-24 |
EP2793833A2 (en) | 2014-10-29 |
WO2013093823A2 (en) | 2013-06-27 |
JP2018109054A (ja) | 2018-07-12 |
CN104105472A (zh) | 2014-10-15 |
WO2013093823A3 (en) | 2013-08-22 |
KR102009698B1 (ko) | 2019-08-13 |
KR20140116861A (ko) | 2014-10-06 |
US10232047B2 (en) | 2019-03-19 |
CN110075310A (zh) | 2019-08-02 |
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