WO2016121996A1 - 水性外用剤 - Google Patents
水性外用剤 Download PDFInfo
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- WO2016121996A1 WO2016121996A1 PCT/JP2016/052838 JP2016052838W WO2016121996A1 WO 2016121996 A1 WO2016121996 A1 WO 2016121996A1 JP 2016052838 W JP2016052838 W JP 2016052838W WO 2016121996 A1 WO2016121996 A1 WO 2016121996A1
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- acid
- external preparation
- aqueous
- aqueous external
- acidic drug
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- 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
- A61K9/08—Solutions
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- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/196—Carboxylic acids, e.g. valproic acid having an amino group the amino group being directly attached to a ring, e.g. anthranilic acid, mefenamic acid, diclofenac, chlorambucil
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- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/205—Amine addition salts of organic acids; Inner quaternary ammonium salts, e.g. betaine, carnitine
-
- 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
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
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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
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/12—Carboxylic acids; Salts or anhydrides thereof
-
- 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
- A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
- A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Definitions
- the present invention relates to an aqueous external preparation containing an acidic drug or a salt thereof as an active ingredient.
- An object of the present invention is to provide an aqueous external preparation excellent in transdermal absorbability of acidic drugs and excellent in feeling of use.
- the present inventors have found that the above problems can be solved by an aqueous external preparation containing isostearic acid and alkanolamine, and have completed the present invention. That is, the present invention provides an aqueous external preparation containing an acidic drug or a salt thereof, isostearic acid and alkanolamine.
- the aqueous external preparation of the present invention preferably further contains a C 2-6 aliphatic hydroxy acid and has a pH of 4.5 to 7.8.
- the C 2-6 aliphatic hydroxy acid may be one or a combination of two or more selected from the group consisting of lactic acid, glycolic acid, malic acid, tartaric acid, and citric acid.
- the above-mentioned acidic drug is preferably an arylacetic acid non-steroidal anti-inflammatory analgesic.
- the aqueous external preparation of the present invention preferably further contains glycerin.
- the aqueous topical preparation of the present invention is excellent in percutaneous absorption, and when the drug is an anti-inflammatory analgesic agent such as an arylacetic acid non-steroidal anti-inflammatory analgesic agent, a sufficient anti-inflammatory analgesic effect is expected in a short time.
- an anti-inflammatory analgesic agent such as an arylacetic acid non-steroidal anti-inflammatory analgesic agent
- the aqueous external preparation of the present invention is also excellent in usability and can be suitably used as a liquid agent used by filling in a coating device having a foamed resin or a ball at the tip.
- the aqueous external preparation of the present invention contains an acidic drug or a salt thereof as an active ingredient.
- Acidic drugs include phenylacetic acid non-steroidal anti-inflammatory analgesics such as alclofenac, diclofenac and felbinac; indole acetic acid non-steroidal anti-inflammatory analgesics such as indomethacin, etodolac and acemetacin; salicylic acids such as salicylic acid, aspirin, etenzaamide and diflunisal Non-steroidal anti-inflammatory analgesics; ibuprofen, ketoprofen, zaltoprofen, suprofen, pranoprofen, flurbuprofen, loxoprofen, and other propionic acid-based nonsteroidal anti-inflammatory drugs; fenamic acid-based nonsteroidal anti-inflammatory drugs such as mefenamic acid Antibiotics such as cefazoline, penicillamine, imipenam,
- arylacetic acid-based nonsteroidal anti-inflammatory analgesics such as phenylacetic acid-based nonsteroidal anti-inflammatory analgesics and indoleacetic acid-based nonsteroidal anti-inflammatory analgesics are preferable, and phenylacetic acid-based nonsteroidal anti-inflammatory analgesics are particularly preferable.
- acidic drug salts include alkali metal salts such as sodium and potassium; alkaline earth metal salts such as calcium and magnesium; ammonium salts; alkylamine salts such as dimethylamine, diethylamine, and trimethylamine; Examples thereof include cyclic amine salts such as ethylpyrrolidine salt).
- the content of the acidic drug or a salt thereof is not particularly limited, but is selected from the range of, for example, 0.1 to 20% by weight, preferably 0.1 to 10% by weight, particularly preferably 0.5 to 5% by weight. be able to. If the content of the acidic drug or a salt thereof is less than the above range, sufficient medicinal effects may not be obtained, which is not preferable. When the content of the acidic drug or a salt thereof exceeds the above range, the acidic drug or a salt thereof may not be sufficiently dissolved or may crystallize with time, which is not preferable.
- the aqueous external preparation of the present invention contains water as an essential component and is typically a liquid, but can be applied to jelly, cream, poultice and the like.
- water for example, a solution obtained by dissolving an acidic drug or a salt thereof, isostearic acid, alkanolamine, and, if necessary, a C 2-6 aliphatic hydroxy acid in a mixed solution of water and a lower alcohol, This is a preferred embodiment.
- fatty acids are used as a transdermal absorption enhancer
- the use of isostearic acid increases the transdermal absorption of the drug compared to the use of other fatty acids. Improve dramatically.
- the acidic drug is an arylacetic acid non-steroidal anti-inflammatory analgesic
- the content of isostearic acid can be selected, for example, from the range of 0.5 to 20% by weight, preferably 2 to 15% by weight, particularly preferably 3 to 10% by weight, based on the weight of the aqueous external preparation.
- 0.1 to 8 times mol preferably 0.5 to 3 times mol, more preferably 1.0 to 2.5 times mol, and particularly preferably 1.5 to 2 times mol, of the acidic drug or a salt thereof. It can be selected from a range of 4 moles.
- alkanolamine for example, any primary, secondary, or tertiary alkanolamine having about 2 to 12 carbon atoms can be used, but a tertiary alkanolamine such as triethanolamine or triisopropanolamine can be used. Is preferred.
- the content of alkanolamine can be selected from the range of 0.4 to 8.0 mol times, preferably 0.5 to 4.0 times mol of the content of isostearic acid.
- the acidic drug is a phenylacetic acid non-steroidal anti-inflammatory analgesic such as diclofenac
- the alkanolamine content is 0.4 to 1.5 times the mole of isostearic acid, particularly preferably 0.6 to 1. It can be selected from a range of 2 moles.
- the acidic drug is an indoleacetic acid non-steroidal anti-inflammatory analgesic such as indomethacin
- the alkanolamine content is 2.5 to 8.0 times the mole of isostearic acid, preferably 3.0 to 4. It can be selected from the range of 0 times mole.
- the content of alkanolamine is, for example, 0.2 to 2.5 with respect to the sum of isostearic acid and aliphatic hydroxy acid. It can be selected from the range of mole times, preferably 0.3 to 1.2 mole times, particularly preferably 0.4 to 0.8 mole times. If the amount of alkanolamine added is outside the above range, the aqueous external preparation may not be a uniform solution or may be separated by stimulation with time or vibration, etc., which is not preferable.
- the alkanolamine content is 0.6 to 1.2 times the mol of isostearic acid, and isostearic acid and fat
- the total amount with the group hydroxy acid is preferably 0.3 to 0.5 times mol.
- the acidic drug is an indoleacetic acid non-steroidal anti-inflammatory analgesic such as indomethacin
- the alkanolamine content is 3.0 to 4.5 times the mole of isostearic acid, and isostearic acid and fat
- the total amount with the group hydroxy acid is preferably 0.6 to 0.9 times mol.
- C 2-6 aliphatic hydroxy acid examples include lactic acid, glycolic acid, malic acid, tartaric acid and citric acid.
- C 2-6 aliphatic hydroxy acids can be used alone or in combination of two or more.
- adjusting the liquidity of the aqueous external preparation to an appropriate range increases the solubility of the acidic drug, and does not cause crystal precipitation or separation even after long-term storage.
- the transdermal absorbability of acidic drugs is improved.
- aqueous external preparation of the present invention containing isostearic acid and alkanolamine, separation becomes easier when the liquidity becomes acidic, but it becomes a stable liquid agent by containing C 2-6 aliphatic hydroxy acid.
- the content of the C 2-6 aliphatic hydroxy acid can be appropriately adjusted so that the liquidity of the aqueous external preparation falls within an appropriate range described later, and is not particularly limited. For example, it can be selected from the range of 1.0 to 10 mol times, preferably 1.0 to 5.0 mol times, particularly preferably 1.5 to 3.5 mol times with respect to the acidic drug.
- the C 2-6 aliphatic hydroxy acid preferably contains at least tartaric acid or lactic acid, and particularly preferably contains tartaric acid.
- tartaric acid not only the stability of the aqueous external preparation is improved, but also the transdermal absorbability is particularly improved. This is because tartaric acid is easily soluble in both aqueous and fatty solvents. This is thought to be due to easy penetration.
- the aqueous external preparation of the present invention has a liquidity of pH 4.5 to 7.8, preferably pH 5.6 to 7.5, more preferably pH 5.0 to 6.8, particularly preferably 5.0 to 5.8. Most preferably, it can be selected from the range of 5.2 to 5.5. If the pH is outside the above range, it may be inferior in stability of the aqueous external preparation, such as precipitation of crystals over time, or may cause skin irritation and the like.
- the pH of the aqueous external preparation can be adjusted by the content of the above-mentioned isostearic acid, alkanolamine, and hydroxy acid, and further adjusted with a pH adjuster such as hydrochloric acid, sodium hydroxide, potassium hydroxide, etc. Also good.
- Examples of the lower alcohol used as a solvent by mixing with water include monovalent or divalent alcohols having 2 to 5 carbon atoms such as ethanol, propanol, isopropanol, and propylene glycol.
- a lower alcohol can be used 1 type or in combination of 2 or more types.
- the content of the lower alcohol can be selected from the range of, for example, 20 to 70% by weight, preferably 40 to 60% by weight, taking into account, for example, the solubility of diclofenac or a salt thereof, the feeling of use, and the like.
- isopropanol and propylene glycol are preferably used in combination at a ratio of, for example, 1: 3 to 3: 1, preferably 1: 2 to 2: 1, particularly preferably 1: 1 to 1: 2. .
- the aqueous external preparation of the present invention contains at least 10% by weight, preferably 20% by weight, particularly preferably 25% by weight or more of water.
- the external preparation of the present invention preferably further contains glycerin.
- glycerin When glycerin is contained, the skin permeation rate of an acidic drug or a salt thereof is improved, and the acidic drug or a salt thereof permeates through the skin immediately after adaptation to the skin, thereby obtaining an external preparation excellent in immediate effect.
- the content of glycerin can be selected, for example, from the range of 0.1 to 10% by weight, preferably 0.2 to 5% by weight, particularly preferably 0.2 to 1.0% by weight. If the glycerin content is less than the above range, it is difficult to obtain the effect of improving the permeation rate, and if the content is more than the above range, the effect is not enhanced, and the skin permeability may be inferior.
- the aqueous external preparation of the present invention may further contain a lipophilic component as a solubilizing agent or transdermal absorption enhancer for an acidic drug or a salt thereof.
- the lipophilic component can be blended in a range of less than 20% by weight, preferably less than 15% by weight of the aqueous external preparation.
- examples of the lipophilic component include fatty acid esters such as isopropyl myristate, isopropyl palmitate and diethyl sebacate; N-methylpyrrolidone; dimethyl isosorbide and the like. Of these, N-methylpyrrolidone or dimethylisosorbide is preferred.
- the aqueous external preparation of the present invention may contain additives such as a thickener, a humectant, a solubilizer, a stabilizer, and a fragrance as necessary.
- a thickener include celluloses such as methylcellulose, hydroxymethylcellulose, hydroxyethylcellulose, carmellose, carmellose sodium, and carmellose calcium; polyvinylpyrrolidone; polyvinyl alcohol; carboxyvinyl polymer; polyacrylate such as sodium polyacrylate Can be illustrated.
- the content of the thickener can be selected, for example, from the range of 0.05 to 20% by weight.
- the aqueous external preparation of the present invention is a liquid, it can be selected from the range of 0.05 to 0.5% by weight.
- the stabilizer include sodium sulfite and sodium pyrosulfite.
- aqueous external preparation The aqueous external preparation of the composition (weight%) shown in Table 1 and Table 2 was prepared. The pH of each agent was measured. Moreover, the external appearance when the aqueous external preparation was filled in a glass container was observed with the naked eye. The results are shown in Tables 1 and 2 together. The appearance was evaluated according to the following criteria. ⁇ : Clear solution ⁇ : A transparent solution is obtained, but it is separated into an oil phase and an aqueous phase over time or by stimulation such as vibration.
- Example 1 and Example 2 of the present invention containing isostearic acid and alkanolamine showed higher skin permeability than the agent of Comparative Example 5 not containing both.
- the liquid preparations of Comparative Examples 1 to 4 containing decanoic acid and levulinic acid as fatty acids instead of isostearic acid were inferior in skin permeability to the agent of Comparative Example 5.
- the agent of Example 3 showed better skin permeability than the agent of Example 2 by further containing lactic acid.
- the agent of Example 4 showed skin permeability superior to that of Example 3 by further containing glycerin.
- the aqueous external preparations of Examples 7 to 9 having a low organic amine content tended to have slightly poor skin permeability.
- the aqueous external preparation of the present invention was excellent in skin permeability, and up to about 3 times as much diclofenac skin permeation was observed as compared with a commercially available diclofenac sodium solution.
- the liquid agent of Example 5 containing glycerin has a high permeation rate.
- Example 12 to 21 An aqueous external preparation having the composition (% by weight) shown in Table 3 was prepared. The pH of each agent was measured. Moreover, the external appearance when the aqueous external preparation was filled in a glass container was observed with the naked eye. The results are also shown in Table 3. The appearance was evaluated according to the following criteria. ⁇ : Clear solution ⁇ : A transparent solution is obtained, but it is separated into an oil phase and an aqueous phase over time or by stimulation such as vibration.
- any of the external preparations having a pH in the range of 5.0 to 7.5 was a stable liquid agent that did not cause separation after storage.
- FIG. 2 shows a graph showing the transition of the cumulative skin permeation amount of diclofenac.
- Examples 2-1 to 2-6 An aqueous external preparation containing indomethacin having the composition (% by weight) shown in Table 4 as an active ingredient was prepared. The pH of each agent was measured. Moreover, the external appearance when the aqueous external preparation was filled in a glass container was observed with the naked eye. The results are shown in 4. The appearance was evaluated according to the following criteria. ⁇ : Clear solution
- the aqueous external preparation of the present invention can be used as a liquid agent that quickly exhibits an excellent anti-inflammatory analgesic effect, in particular, as a liquid agent that is used by filling in a coating device having a foamed resin or a ball at the tip.
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Abstract
Description
表1及び表2に示す組成(重量%)の水性外用剤を調製した。各剤のpHを測定した。また、水性外用剤をガラス容器に充填したときの外観を肉眼で観察した。結果を表1及び2に併せて示す。
外観の評価は以下の基準で行った。
○:澄明な溶液
△:透明な溶液が得られるが経時的に又は振動等の刺激により油相と水相に分離する
調整した水性外用剤及び市販の1%ジクロフェナクナトリウム液剤について、常法に従ってフランツ・セルを用いた皮膚透過性試験を行った。試験にはラット(5週齢、ウィスターラット、雄)の腹部摘出皮膚を用いた。試験開始後2、4、6時間後にサンプリングを行った。6時間後の累積透過量を表1及び2に併せて示す。実施例3、5、11、及び市販の液剤の累積皮膚透過量の推移を表すグラフを図1に示す。
表3に示す組成(重量%)の水性外用剤を調製した。各剤のpHを測定した。また、水性外用剤をガラス容器に充填したときの外観を肉眼で観察した。結果を表3に併せて示す。
外観の評価は以下の基準で行った。
○:澄明な溶液
△:透明な溶液が得られるが経時的に又は振動等の刺激により油相と水相に分離する
表4に示す組成(重量%)のインドメタシンを活性成分として含む水性外用剤を調製した。各剤のpHを測定した。また、水性外用剤をガラス容器に充填したときの外観を肉眼で観察した。結果を4に示す。
外観の評価は以下の基準で行った。
○:澄明な溶液
Claims (5)
- 酸性薬物又はその塩と、イソステアリン酸、及びアルカノールアミンを含む、水性外用剤。
- さらに、C2-6脂肪族ヒドロキシ酸を含み、pHが4.5~7.8である、請求項1に記載の水性外用剤。
- 上記C2-6脂肪族ヒドロキシ酸が、乳酸、グリコール酸、リンゴ酸、酒石酸、クエン酸から成る群より選択される1種又は2種以上の組み合わせである、請求項1又は2に記載の水性外用剤。
- 上記酸性薬物が、アリール酢酸系非ステロイド性消炎鎮痛剤である、請求項1~3いずれかの項に記載の水性外用剤。
- さらに、グリセリンを含む、請求項1~4のいずれかの項に記載の水性外用剤。
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2016572213A JP6676548B2 (ja) | 2015-01-30 | 2016-01-29 | 水性外用剤 |
BR112017016010-2A BR112017016010B1 (pt) | 2015-01-30 | 2016-01-29 | Preparação aquosa para uso externo. |
US15/546,798 US11090265B2 (en) | 2015-01-30 | 2016-01-29 | Aqueous preparation for external use |
CN201680006476.3A CN107148284A (zh) | 2015-01-30 | 2016-01-29 | 水性外用制剂 |
EP16743599.9A EP3251695A4 (en) | 2015-01-30 | 2016-01-29 | Aqueous preparation for external use |
US17/382,272 US20210353539A1 (en) | 2015-01-30 | 2021-07-21 | Aqueous Preparation for External Use |
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JP2015-016365 | 2015-01-30 | ||
JP2015016365 | 2015-01-30 | ||
JP2015110902 | 2015-05-29 | ||
JP2015-110902 | 2015-05-29 |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
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US15/546,798 A-371-Of-International US11090265B2 (en) | 2015-01-30 | 2016-01-29 | Aqueous preparation for external use |
US17/382,272 Continuation US20210353539A1 (en) | 2015-01-30 | 2021-07-21 | Aqueous Preparation for External Use |
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WO2016121996A1 true WO2016121996A1 (ja) | 2016-08-04 |
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US (2) | US11090265B2 (ja) |
EP (1) | EP3251695A4 (ja) |
JP (2) | JP6676548B2 (ja) |
CN (1) | CN107148284A (ja) |
BR (1) | BR112017016010B1 (ja) |
WO (1) | WO2016121996A1 (ja) |
Families Citing this family (1)
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BR112017016010B1 (pt) * | 2015-01-30 | 2023-02-14 | Medrx Co., Ltd | Preparação aquosa para uso externo. |
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WO1991012821A1 (en) * | 1990-03-02 | 1991-09-05 | Shiseido Company, Ltd. | Oil-in-water emulsion composition containing nonsteroidal antiphlogistic analgesic |
WO2004064817A1 (ja) * | 2003-01-22 | 2004-08-05 | Nichiban Co., Ltd. | 眼疾患治療用経皮吸収型製剤、その使用、及び眼疾患治療薬の眼の局所組織への移行方法 |
JP2009519958A (ja) * | 2005-12-14 | 2009-05-21 | ザーズ, インコーポレイテッド | 薬物の皮膚送達のための、フラックス化可能な組成物および方法 |
JP2009519956A (ja) * | 2005-12-14 | 2009-05-21 | ザーズ, インコーポレイテッド | 薬物の皮膚送達のための組成物および方法 |
JP2009519940A (ja) * | 2005-12-14 | 2009-05-21 | ザーズ, インコーポレイテッド | 皮膚科学的状態を処置するための組成物および方法 |
WO2009066457A1 (ja) * | 2007-11-22 | 2009-05-28 | Medrx Co., Ltd. | 脂肪酸系イオン液体を有効成分とする外用剤組成物 |
WO2010103844A1 (ja) * | 2009-03-11 | 2010-09-16 | 興和株式会社 | 鎮痛・抗炎症剤含有外用剤 |
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Publication number | Priority date | Publication date | Assignee | Title |
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2016
- 2016-01-29 BR BR112017016010-2A patent/BR112017016010B1/pt active IP Right Grant
- 2016-01-29 JP JP2016572213A patent/JP6676548B2/ja active Active
- 2016-01-29 CN CN201680006476.3A patent/CN107148284A/zh active Pending
- 2016-01-29 EP EP16743599.9A patent/EP3251695A4/en active Pending
- 2016-01-29 US US15/546,798 patent/US11090265B2/en active Active
- 2016-01-29 WO PCT/JP2016/052838 patent/WO2016121996A1/ja active Application Filing
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2020
- 2020-03-12 JP JP2020042557A patent/JP6956426B2/ja active Active
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2021
- 2021-07-21 US US17/382,272 patent/US20210353539A1/en not_active Abandoned
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Also Published As
Publication number | Publication date |
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JPWO2016121996A1 (ja) | 2017-11-09 |
BR112017016010B1 (pt) | 2023-02-14 |
US20180015037A1 (en) | 2018-01-18 |
US20210353539A1 (en) | 2021-11-18 |
EP3251695A1 (en) | 2017-12-06 |
BR112017016010A2 (ja) | 2018-03-20 |
CN107148284A (zh) | 2017-09-08 |
EP3251695A4 (en) | 2018-08-01 |
JP6676548B2 (ja) | 2020-04-08 |
JP6956426B2 (ja) | 2021-11-02 |
JP2020109111A (ja) | 2020-07-16 |
US11090265B2 (en) | 2021-08-17 |
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