WO2014091729A1 - 基剤、及び皮膚外用剤 - Google Patents
基剤、及び皮膚外用剤 Download PDFInfo
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- WO2014091729A1 WO2014091729A1 PCT/JP2013/007185 JP2013007185W WO2014091729A1 WO 2014091729 A1 WO2014091729 A1 WO 2014091729A1 JP 2013007185 W JP2013007185 W JP 2013007185W WO 2014091729 A1 WO2014091729 A1 WO 2014091729A1
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- base
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- weight
- volatile oil
- external preparation
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- 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
-
- 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
- A61K31/66—Phosphorus compounds
- A61K31/665—Phosphorus compounds having oxygen as a ring hetero atom, e.g. fosfomycin
-
- 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
- A61K47/24—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing atoms other than carbon, hydrogen, oxygen, halogen, nitrogen or sulfur, e.g. cyclomethicone or phospholipids
-
- 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
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
-
- 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
- A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin
-
- 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
- A61K8/31—Hydrocarbons
-
- 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
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- A61K8/8147—Homopolymers or copolymers of acids; Metal or ammonium salts thereof, e.g. crotonic acid, (meth)acrylic acid; Compositions of derivatives of such polymers
-
- 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
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- A61K8/8158—Homopolymers or copolymers of amides or imides, e.g. (meth) acrylamide; Compositions of derivatives of such polymers
-
- 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
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/89—Polysiloxanes
- A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
- A61K8/893—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone modified by an alkoxy or aryloxy group, e.g. behenoxy dimethicone or stearoxy dimethicone
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
-
- 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
- A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
- A61K9/7015—Drug-containing film-forming compositions, e.g. spray-on
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q15/00—Anti-perspirants or body deodorants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/005—Preparations for sensitive skin
Definitions
- the present invention relates to a base used for an external preparation for skin in which an active ingredient is administered transdermally, and an external preparation for skin.
- An external preparation for skin is a dosage form in which an active ingredient is dissolved or dispersed in a liquid or ointment (cream) base, and the active ingredient is administered percutaneously by being applied to the skin surface. It is.
- the external preparation for skin described in Patent Document 1 is prepared by dissolving nitrocellulose in a solubilizing agent such as 3-methylbutyl acetate, isobutyl acetate, or acetone, and further adding ethyl alcohol. Since nitrocellulose has explosive properties, it is difficult to handle it, and it is difficult to ensure production safety.
- a solubilizing agent such as 3-methylbutyl acetate, isobutyl acetate, or acetone
- solubilizers such as acetic acid-3-methylbutyl, isobutyl acetate, and acetone have odor generation and skin irritation, and are not necessarily preferable as a component of an external preparation for skin.
- the present invention has been developed in view of the above technical problems, and can be quickly formed after application to the skin surface, and further, a novel base that reduces odor generation and skin irritation, And it aims at providing a skin external preparation.
- the base of the present invention is a base used for an external preparation for skin in which an active ingredient is administered percutaneously, and includes at least an acrylic synthetic polymer and a volatile oil. And is in a liquid or ointment form before application to the skin surface, and after application, the volatile oil evaporates, and the volatile oil agent is 0 to 100 parts by weight of the acrylic synthetic polymer. It is characterized by being a hydrophobic coating within the range of 60% by weight (hereinafter referred to as “the base of the present invention”).
- a preferred embodiment has a hydrophobicity with a weight change rate (X) by the following test of 5.0% or less.
- the acrylic synthetic polymer is an alkyl acrylate copolymer, an alkyl acrylate copolymer sodium, an alkyl acrylate copolymer ammonium, an (alkyl acrylate / diacetone acrylamide) copolymer, Alternatively, at least one selected from (alkyl acrylate / dimethicone) copolymers is a preferred embodiment.
- a preferred embodiment is one in which the volatile oil is at least one selected from short-chain paraffin or volatile silicone oil.
- the external preparation for skin of the present invention comprises the base of the present invention and an active ingredient, and is in a liquid or ointment form before application to the skin surface, and after application, the volatile oil agent is Vaporized to form a hydrophobic film in which the volatile oil agent is in the range of 0 to 60% by weight with respect to 100 parts by weight of the acrylic synthetic polymer (hereinafter referred to as “the external preparation of the present invention”). Called).
- a preferred embodiment is one that is used by applying a foundation from above the coating after forming a hydrophobic coating after application to the skin surface.
- a coating can be formed quickly after application to the skin surface, and the generation of odor and skin irritation can be alleviated.
- compositions (before application) of the bases of the present invention according to Examples 1 to 7 are shown in Table 1 below.
- the bases of the present invention according to Examples 1 to 7 all remain in a liquid or ointment form before being applied to the skin surface, and when applied to the skin surface, the volatile oils evaporate and quickly appear on the skin surface. It was confirmed that a film was formed on the film.
- the base of the present invention uses an acrylic resin as a film forming component, and uses a volatile oil (short chain paraffin (liquid isoparaffin) or volatile silicone oil) as a volatile component when applied to the skin surface. Therefore, odor generation and skin irritation are very low.
- a volatile oil short chain paraffin (liquid isoparaffin) or volatile silicone oil
- the cotton nonwoven fabric that has been immersed and dried is put into water, stirred for 1 hour, then pulled up from the water, wiped off moisture adhering to the surface, weighed (W), and calculated by the formula:
- X The weight change rate (X) is measured at (WD) ⁇ 100 / D.
- the bases of the present invention according to Examples 1 to 7 showed high hydrophobicity with a weight change rate (X) of 5% or less.
- the bases of the present invention according to Examples 5 to 7 using (alkyl acrylate / dimethicone) copolymer as an acrylic resin have a very high hydrophobicity with a weight change rate (X) of 2% or less. It was confirmed to show.
- the weight change rate (X) was confirmed to be 500% or more.
- Example 8 The external preparation of the present invention was obtained by blending sodium base of tocopheryl phosphate (TPNa) as an active ingredient with respect to the base of the present invention according to Example 6 so as to have an addition amount of 5% by weight.
- TPNa tocopheryl phosphate
- the obtained external preparation of the present invention was subjected to the following test to evaluate the skin permeability of the active ingredient.
- the stratum corneum / skin layer of human skin is cut into a circle having a diameter of 30 mm and used for the test.
- the diffusion cell is a Franz diffusion cell (effective area 3.14 cm 2 , receptor volume 2.4 ml), and the receptor solution is a PBS (phosphate buffered saline, pH 7.4) solution. Is kept at 32 ° C. and the permeability test is carried out in an unsealed system. 1 ml of the base of the present invention is administered to the donor side, and after 5 minutes, 1 ml of PBS solution is added to the donor side and gently washed, and then the donor side solution is discarded. This cleaning operation is performed twice (three times for convenience).
- TPNa in the sampled solution is measured by HPLC (high performance liquid chromatography).
- the external preparation of the present invention can continuously administer the active ingredient percutaneously even after the surface of the film is washed three times after the film is formed. It was. This is presumably because the base of the present invention becomes a hydrophobic coating, adheres to the skin surface without being washed away even by repeated washing, and continuously administers the active ingredient percutaneously.
- the external preparation of the present invention can be administered percutaneously absorbably for a long time without peeling off even after bathing or washing the face after forming a film.
- the formed film is not sticky, the foundation can be applied on the film. Therefore, it can be used in a state where the film is covered with a foundation.
- the formed film can be easily removed from the skin surface using cleansing oil or the like.
- the external preparation of the present invention does not deny that other additives other than the active ingredient, for example, various additives such as a moisturizer, an antiseptic, an antioxidant and a pH adjuster are blended.
- various additives such as a moisturizer, an antiseptic, an antioxidant and a pH adjuster are blended.
- the active ingredient of the external preparation of the present invention is not limited to TPNa, and various active ingredients can be used according to the purpose of the external preparation of the present invention.
- active ingredients include, for example, corticosteroids, anti-inflammatory analgesics, hypertensives, anesthetics, hypnotic sedatives, tranquilizers, antihypertensives, antibiotics, antibacterial substances, vitamins, antiepileptics, coronary Vasodilators, antihistamines, antifungal substances, sublimable crystals, mint oil, eucalyptus oil, lavender oil, boric acid water, physiological saline, sulfite, flaxseed oil, lime water, liver oil, ribanol water, potassium permanganate Liquids, mental water, creosote, mustard, anti-inflammatory agents, astringents, refreshing agents, vitamins, hormones, antihistamines and other anti-rough skin agents, sebum suppressants, exfoliating and dissolv
- the base of the present invention is suitably used as a base for an external preparation for skin (the external preparation of the present invention) for administering an active ingredient percutaneously.
Abstract
Description
前記基剤に、コットン不織布(10cm×10cm、目付60g/m2)を浸漬し、60℃の恒温槽内で24時間乾燥させた後の重量(D)を測る。次いで、浸漬、乾燥後の前記コットン不織布を水中に投入し、1時間撹拌した後、水中から引き上げ、表面に付着している水分を拭き取ったうえで重量(W)を測り、下記計算式により、重量変化率(X)を求める。計算式:X=(W-D)×100/D
実施例1~7に係る本発明基剤の組成(塗布前)を下記表1に示す。
実施例1~7に係る本発明基剤は、皮膚表面に塗布する前はいずれも液状又は軟膏状を維持しており、皮膚表面に塗布すると揮発性油剤が蒸散して、皮膚表面上において速やかに被膜を形成することが確認された。
実施例1~7に係る本発明基剤をガラス板表面に一定量塗布した後、35℃の恒温槽内で乾燥させ、塗布時と乾燥後の本発明基剤の重量変化を比較して、ガラス表面に形成された被膜に残存する揮発性油剤の残存量を測定した。その結果、いずれの実施例においても、アクリル系樹脂100重量部に対し、揮発性油剤が0~60重量部の範囲内で残存する被膜が形成されていることが確認された。特に、揮発性油剤として軽質イソパラフィンを用いた実施例3~7に係る本発明基剤にて形成された被膜は、アクリル系樹脂100重量部に対し、揮発性油剤が0~30重量部の範囲内となっていることが確認された。
次に、実施例1~7に係る本発明基剤によって形成される被膜の疎水性を下記試験条件によって評価した。
実施例1~7に係る本発明基剤に、コットン不織布(10cm×10cm、目付60g/m2)を浸漬し、60℃の恒温槽内で24時間乾燥させた後の重量(D)を測る。次いで、浸漬、乾燥後の前記コットン不織布を水中に投入し、1時間撹拌した後、水中から引き上げ、表面に付着している水分を拭き取ったうえで重量(W)を測り、計算式:X=(W-D)×100/Dにて、重量変化率(X)を測定する。
前記実施例6に係る本発明基剤に対し、有効成分としてのトコフェリルリン酸ナトリウム(TPNa)を5重量%の添加量となるように配合することによって、本発明外用剤を得た。
ヒト皮膚の角質層/表質層を直径30mmの円状にカットして試験に用いる。拡散セルはフランツ型拡散セル(有効面積3.14cm2、レセプター容積2.4ml)を用い、レセプター溶液にはPBS(リン酸緩衝生理食塩水、pH7.4)溶液を用いて、拡散セルの温度を32℃に保ち、非密封系で透過性試験を実施する。本発明基剤1mlをドナー側に投与し、5分後に、ドナー側にPBS溶液1mlを加えて軽く洗浄後、ドナー側の溶液を廃棄する。この洗浄作業は更に二回(都合三回)行う。この後、3時間後、6時間後、12時間後にレセプターから1mlをサンプリングする(3時間後と6時間後においては、レセプターにPBS溶液1mlを加える。)。サンプリングした溶液中のTPNaを、HPLC(高速液体クロマトグラフィー)により測定する。
カラム:CAPCELLPAK C18、TypeMG 5μm 4.6I.D.×250mm(株式会社資生堂製)
移動相:(20mM酢酸+20mM酢酸ナトリウムメタノール)/アセトンニトリル=7/3
流速:1.0ml/分
温度:40℃
注入量:10μl
上記試験結果を、下記表2に示す。
Claims (6)
- 有効成分を経皮吸収的に投与する皮膚外用剤に用いられる基剤であって、
アクリル系合成ポリマーと揮発性油剤とを少なくとも含有し、皮膚表面への塗布前には、液状又は軟膏状であり、
塗布後には、前記揮発性油剤が蒸散して、前記アクリル系合成ポリマー100重量部に対して前記揮発性油剤が0~60重量%範囲内の、疎水性の被膜となることを特徴とする基剤。 - 請求項1に記載の基剤において、
下記試験による重量変化率(X)が、5.0%以下となる疎水性を有する基剤。
<試験>
前記基剤に、コットン不織布(10cm×10cm、目付60g/m2)を浸漬し、60℃の恒温槽内で24時間乾燥させた後の重量(D)を測る。
次いで、浸漬、乾燥後の前記コットン不織布を水中に投入し、1時間撹拌した後、水中から引き上げ、表面に付着している水分を拭き取ったうえで重量(W)を測り、下記計算式により、重量変化率(X)を求める。
計算式:X=(W-D)×100/D - 請求項1又は2に記載の基剤において、
前記アクリル系合成ポリマーが、アクリル酸アルキル共重合体、アクリル酸アルキル共重合体ナトリウム、アクリル酸アルキル共重合体アンモニウム、(アクリル酸アルキル/ジアセトンアクリルアミド)共重合体、又は、(アクリル酸アルキル/ジメチコン)共重合体から選ばれた少なくとも一種以上である基剤。 - 請求項1ないし3のいずれか1項に記載の基剤において、
前記揮発性油剤が、短鎖パラフィン、又は揮発性シリコーンオイルから選ばれた少なくとも一種以上である基剤。 - 請求項1ないし4のいずれか1項に記載の基剤と、
有効成分と、
を具備してなり、皮膚表面への塗布前には、液状又は軟膏状であり、
塗布後には、前記揮発性油剤が蒸散して、疎水性の被膜となることを特徴とする皮膚外用剤。 - 請求項5に記載の皮膚外用剤において、
皮膚表面へ塗布後、疎水性の被膜となった後、前記被膜上からファンデーションが塗布されることによって使用される基剤。
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
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EP13862500.9A EP2910254B1 (en) | 2012-12-11 | 2013-12-06 | Base and external preparation for skin |
CN201380064556.0A CN104936619A (zh) | 2012-12-11 | 2013-12-06 | 主剂以及皮肤外用剂 |
US14/650,701 US20160184331A1 (en) | 2012-12-11 | 2013-12-06 | Base and external preparation for skin |
HK16102659.0A HK1214538A1 (zh) | 2012-12-11 | 2016-03-08 | 主劑以及皮膚外用劑 |
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JP2012-270153 | 2012-12-11 | ||
JP2012270153A JP2014114249A (ja) | 2012-12-11 | 2012-12-11 | 基剤、及び皮膚外用剤 |
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WO2014091729A1 true WO2014091729A1 (ja) | 2014-06-19 |
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PCT/JP2013/007185 WO2014091729A1 (ja) | 2012-12-11 | 2013-12-06 | 基剤、及び皮膚外用剤 |
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US (1) | US20160184331A1 (ja) |
EP (1) | EP2910254B1 (ja) |
JP (1) | JP2014114249A (ja) |
KR (1) | KR20150084839A (ja) |
CN (1) | CN104936619A (ja) |
HK (1) | HK1214538A1 (ja) |
WO (1) | WO2014091729A1 (ja) |
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JP2018531231A (ja) * | 2015-09-16 | 2018-10-25 | ディーエフビー ソリア リミテッド ライアビリティ カンパニー | 薬物ナノ粒子の送達およびその使用法 |
US10842736B2 (en) | 2017-03-15 | 2020-11-24 | Dfb Soria, Llc | Topical therapy for the treatment of skin malignancies using nanoparticles of taxanes |
US11497726B2 (en) | 2018-03-16 | 2022-11-15 | Dfb Soria, Ll. | Topical therapy for the treatment of cervical intraepithelial neoplasia (CIN) and cervical cancer using nanoparticles of taxanes |
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US10898470B1 (en) | 2019-08-13 | 2021-01-26 | Sato Pharmaceutical Co., Ltd. | Pharmaceutical composition containing antifungal agent as active ingredient |
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2013
- 2013-12-06 US US14/650,701 patent/US20160184331A1/en not_active Abandoned
- 2013-12-06 CN CN201380064556.0A patent/CN104936619A/zh active Pending
- 2013-12-06 WO PCT/JP2013/007185 patent/WO2014091729A1/ja active Application Filing
- 2013-12-06 EP EP13862500.9A patent/EP2910254B1/en not_active Not-in-force
- 2013-12-06 KR KR1020157012362A patent/KR20150084839A/ko not_active Application Discontinuation
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2016
- 2016-03-08 HK HK16102659.0A patent/HK1214538A1/zh unknown
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Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2018531231A (ja) * | 2015-09-16 | 2018-10-25 | ディーエフビー ソリア リミテッド ライアビリティ カンパニー | 薬物ナノ粒子の送達およびその使用法 |
US10918606B2 (en) | 2015-09-16 | 2021-02-16 | Dfb Soria, Llc | Delivery of drug nanoparticles and methods of use thereof |
US11331278B2 (en) | 2015-09-16 | 2022-05-17 | Dfb Soria, Llc | Delivery of drug nanoparticles and methods of use thereof |
US10842736B2 (en) | 2017-03-15 | 2020-11-24 | Dfb Soria, Llc | Topical therapy for the treatment of skin malignancies using nanoparticles of taxanes |
US11191717B2 (en) | 2017-03-15 | 2021-12-07 | Dfb Soria, Llc | Topical therapy for the treatment of skin malignancies using nanoparticles of taxanes |
US11633349B2 (en) | 2017-03-15 | 2023-04-25 | Dfb Soria, Llc | Topical therapy for the treatment of skin malignancies using nanoparticles of taxanes |
US11497726B2 (en) | 2018-03-16 | 2022-11-15 | Dfb Soria, Ll. | Topical therapy for the treatment of cervical intraepithelial neoplasia (CIN) and cervical cancer using nanoparticles of taxanes |
Also Published As
Publication number | Publication date |
---|---|
KR20150084839A (ko) | 2015-07-22 |
CN104936619A (zh) | 2015-09-23 |
US20160184331A1 (en) | 2016-06-30 |
JP2014114249A (ja) | 2014-06-26 |
EP2910254A1 (en) | 2015-08-26 |
HK1214538A1 (zh) | 2016-07-29 |
EP2910254A4 (en) | 2015-10-28 |
EP2910254B1 (en) | 2017-05-17 |
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