WO2020262299A1 - 皮膚外用剤 - Google Patents

皮膚外用剤 Download PDF

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Publication number
WO2020262299A1
WO2020262299A1 PCT/JP2020/024402 JP2020024402W WO2020262299A1 WO 2020262299 A1 WO2020262299 A1 WO 2020262299A1 JP 2020024402 W JP2020024402 W JP 2020024402W WO 2020262299 A1 WO2020262299 A1 WO 2020262299A1
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Prior art keywords
less
mass
component
skin
external preparation
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Ceased
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PCT/JP2020/024402
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English (en)
French (fr)
Japanese (ja)
Inventor
仁教 衣笠
めぐみ 松岡
渡邊　学
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Kao Corp
Original Assignee
Kao Corp
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Publication date
Application filed by Kao Corp filed Critical Kao Corp
Priority to US17/622,395 priority Critical patent/US20220354868A1/en
Priority to EP20831792.5A priority patent/EP3991794A4/en
Priority to CN202080046286.0A priority patent/CN114126574B/zh
Publication of WO2020262299A1 publication Critical patent/WO2020262299A1/ja
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
    • A61K31/573—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone substituted in position 21, e.g. cortisone, dexamethasone, prednisone or aldosterone
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    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
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    • A61K31/24—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group having an amino or nitro group
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Definitions

  • the present invention relates to an external preparation for skin.
  • inflammatory skin diseases are caused by an overreaction of the living body to an antigen (allergen), that is, an immunological abnormality and an abnormality in the barrier function of the skin.
  • allergen an antigen
  • stratum corneum natural moisturizing factors such as sebum, amino acids, and urea, and intercellular lipids in the stratum corneum such as ceramide and fatty acid keep the skin water content constant, and the pH is also kept weakly acidic.
  • allergen antigen
  • stratum corneum natural moisturizing factors such as sebum, amino acids, and urea, and intercellular lipids in the stratum corneum such as ceramide and fatty acid keep the skin water content constant, and the pH is also kept weakly acidic.
  • atopic dermatitis it is known that these factors in the stratum corneum are reduced, the stratum corneum causes structural abnormalities, the barrier function of the skin is reduced or destroyed, and the pH is increased. Has been done.
  • Patent Document 1 skin cosmetics containing intercellular lipid components, moisturizing components and phospholipids
  • Patent Document 2 skin external preparations containing N-acylglutamic acid diester and pyrrolidone carboxylic acid-modified dimethylpolysiloxane
  • Patent Document 3 an external preparation composition containing the diamide derivative of the above and the lipid component between keratinocytes.
  • Patent Document 1 Japanese Patent Application Laid-Open No. 2004-168763
  • Patent Document 2 Japanese Patent Application Laid-Open No. 2007-210892
  • Patent Document 3 Japanese Patent Application Laid-Open No. 2002-332208
  • Patent Documents 1 to 3 improve the barrier function of the skin, but do not have the function of reducing the contact / permeation of allergens into the skin. There wasn't. Therefore, the present invention not only improves the symptoms of skin diseases, but also enhances the barrier function of the skin, while maintaining the emulsified state and the contained drug in a stable state under the pH of the weakly acidic region, and further contacts the allergen with the skin. -Regarding external skin preparations that can suppress permeation itself.
  • the present inventors have specified medicinal ingredients in a base formulation consisting of a combination of a higher alcohol, two or more specific nonionic surfactants, a phospholipid or a specific anionic surfactant, and water in a specific amount ratio.
  • a base formulation consisting of a combination of a higher alcohol, two or more specific nonionic surfactants, a phospholipid or a specific anionic surfactant, and water in a specific amount ratio.
  • Component (A) fatty alcohol with 14 to 20 carbon atoms
  • a linear aliphatic alcohol is preferable, and a saturated aliphatic alcohol is preferable.
  • Specific examples of the component (A) include myristyl alcohol, cetyl alcohol, stearyl alcohol, and arachidyl alcohol.
  • the component (A) either one can be used alone or in combination of two or more, but from the viewpoint of storage stability in an emulsified state, two or more compounds having different carbon atoms are used in combination. Is preferable. Furthermore, from the same viewpoint, among the components (A), (a2) long-chain (carbon number 18 or more and 20 or less) fatty alcohol, (a1) short-chain (carbon number 14 or more and less than 18) fatty alcohol.
  • the mass ratio (a1) / (a2) of is preferably 0.1 or more, more preferably 0.6 or more, further preferably 1.0 or more, and preferably 7.0 or less, more preferably 5.0 or less, still more preferably 3.0 or less. is there.
  • Component (B) Two or more types of polyhydric alcohol fatty acid ester type nonionic surfactant
  • Ingredients (B) include sucrose fatty acid ester, glycerin fatty acid ester, polyglycerin fatty acid ester, monofatty acid sorbitan, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene sorbit fatty acid ester, polyoxyethylene glycerin fatty acid ester, and polyoxyethylene fatty acid. Examples thereof include SL, polyoxyethylene hydrogenated castor oil, etc., and two or more of these are used in combination.
  • (b1) HLB is 3 or more and 7 or less, more preferably 4 or more and 6 or less, from the viewpoint of forming a dry coating film having a lamellar structure.
  • a combination of one or more esters and one or more polyhydric alcohol fatty acid esters having (b2) HLB of 11 or more and 16, more preferably 13 or more and 15 or less is preferable.
  • these mass ratios (b1) / (b2) are preferably 0.25 or more, more preferably 0.4 or more, still more preferably 0.6 or more, and preferably 4.0 or less, more preferably. Is 2.0 or less, more preferably 1.0 or less.
  • the content of the component (B) in the external preparation for skin of the present invention is preferably 0.5% by mass or more, more preferably 1.0% by mass or more, still more preferably 1.5% by mass or more, from the viewpoint of storage stability in an emulsified state. Also, from the viewpoint of smoothness at the time of coating, it is preferably 5.0% by mass or less, more preferably 4.0% by mass or less, and further preferably 3.0% by mass or less.
  • the mass ratio (A) / (B) of the component (A) to the component (B) in the external preparation for skin of the present invention is 0.3 or more, preferably 0.35 or more, more preferably 0.35 or more from the viewpoint of suppressing allergen permeation. It is 0.4 or more, and from the viewpoint of good elongation at the time of coating, it is 2.0 or less, preferably 1.5 or less, more preferably 1.0 or less, and further preferably 0.8 or less.
  • Component (C) N-acyl amino acid, N-acyl taurine and salts thereof, phospholipid
  • the component (C) is a component that imparts an allergen permeation inhibitory function to a dry film having a lamellar structure formed on the skin.
  • the acyl amino acid and the acyl group of the acyl taurine are derived from fatty acids having a saturated or unsaturated straight chain or branched chain or a mixed fatty acid thereof from the viewpoint of storage stability in the emulsified state. It is preferable that the fatty acid is derived from a linear fatty acid or a mixed fatty acid of a linear fatty acid, and the number of carbon atoms thereof is preferably 6 or more, more preferably 10 or more, still more preferably 12 or more, and preferably 22. Below, it is more preferably 20 or less, still more preferably 18 or less.
  • the acyl group is preferably one or more selected from a capryloyl group, a lauroyl group, a myristoylation group, a palmitoyl group, a stearoyl group, and a cocoyl group, and an acyl group derived from an animal or vegetable oil such as palm oil. It may be.
  • acyl taurine from the viewpoint of storage stability in the emulsified state, coconut oil fatty acid methyl taurine, N-caproyl methyl taurine, N-lauroyl methyl taurine, N-myristoyl methyl taurine, N-palmitoyl methyl taurine, N-stearoyl methyl.
  • taurine and N-oleoyl methyl taurine is preferable, and N-stearoyl methyl taurine is more preferable.
  • acyl amino acid and acyl taurine salts examples include alkali metal salts such as sodium salt and potassium salt; alkaline earth metal salts such as calcium salt and magnesium salt; other metal salts such as aluminum salt and zinc salt; ammonium salt; Organic amine salts such as monoethanolamine salt, diethanolamine salt and triethanolamine salt; basic amino acid salts such as arginine salt, lysine salt, histidine salt and ornithine salt and the like can be mentioned. These may be used individually by 1 type, and may be used in combination of 2 or more type. Among them, as the acyl amino acid salt and the acyl taurine salt, an alkali metal salt is preferable, and a sodium salt is more preferable, from the viewpoint of storage stability in an emulsified state.
  • the phospholipids include lecithin, hydrogenated lecithin, lecithin hydroxide, phosphatidylethanolamine, phosphatidylserine, phosphatidylcholine, phosphatidylinositol, phosphatidylglycerol, cardiolipin and other glycerophospholipids; Examples include sphingolin phospholipids.
  • hydrogenated lecithin is preferable, and soybean hydrogenated lecithin is more preferable, from the viewpoint of suppressing allergen permeation.
  • the component (C) among the above-mentioned specific compounds, those classified into sodium N-acylglutamate, sodium N-acylmethyltaurine and hydrogenated lecithin are preferable from the viewpoint of storage stability in an emulsified state. Any one of the above components (C) can be used alone or in combination of two or more.
  • the content of the component (C) in the external preparation for skin of the present invention is 0.1% by mass or more, preferably 0.2% by mass or more, more preferably 0.2% by mass or more, from the viewpoint of suppressing allergen permeation and improving the storage stability of the emulsified state. It is 0.3% by mass or more, and from the viewpoint of smoothness at the time of coating and suppression of allergen permeation, it is 1.0% by mass or less, preferably 0.8% by mass or less, and more preferably 0.6% by mass or less.
  • the mass ratio (A) / (C) of the component (A) to the component (C) in the external preparation for skin of the present invention is preferably 1.0 or more, more preferably 1.5 or more, still more preferably 1.5 or more, from the viewpoint of suppressing allergen permeation. It is 2.0 or more, and from the viewpoint of storage stability in an emulsified state, it is preferably 15 or less, more preferably 5.0 or less, and further preferably 3.0 or less.
  • the content thereof is preferably 0.025% by mass or more, more preferably 0.05% by mass or more, still more preferably 0.10 from the same viewpoint as above. It is 1% by mass or more, preferably 1.0% by mass or less, more preferably 0.5% by mass or less, and further preferably 0.3% by mass or less.
  • the content thereof is preferably 0.5% by mass or more, more preferably 2.5% by mass or more, still more preferably 4.5% by mass from the same viewpoint as above. It is more preferably 6.5% by mass or less, more preferably 6.0% by mass or less, still more preferably 5.5% by mass or less.
  • the component (D) is a heparinoid
  • its content is preferably 0.01% by mass or more, more preferably 0.1% by mass or more, still more preferably 0.3% by mass or more, from the same viewpoint as above. It is preferably 3.0% by mass or less, more preferably 1.0% by mass or less, and further preferably 0.5% by mass or less.
  • Component (E) Water
  • the content of the component (E) in the external preparation for skin of the present invention is preferably 50% by mass or more, more preferably 60% by mass or more, still more preferably 70% by mass or more, from the viewpoint of good elongation at the time of application. Also, from the viewpoint of suppressing allergen permeation, it is preferably 95% by mass or less, more preferably 90% by mass or less, and further preferably 85% by mass or less.
  • Component (F) Ceramides
  • the external preparation for skin of the present invention can contain ceramides as a component (F) in order to further improve the barrier function of the skin.
  • ceramides include one or more selected from natural ceramides and pseudo-ceramides.
  • specific examples of the natural ceramide include ceramides Types 1 to 7 in which sphingosine, dihydrosphingosine, phytosphingosine or sphingadienin are amidated, and further include these N-alkyl forms (for example, N-methyl form). Is done.
  • pseudo-ceramide examples include (N-hexadecyloxyhydroxypropyl) -N-hydroxyhexadecanamid, (N-hexadecyloxyhydroxypropyl) -N-hydroxydecanamid, and N- [2- ( 2,3-Dihydroxypropyloxy) -3-hexadecyloxypropyl] -N-3-methoxypropyl tetradecaneamide.
  • the content of the component (F) in the external preparation for skin of the present invention is preferably 1.0% by mass or more, more preferably 1.5% by mass or more, still more preferably 2.0% by mass, from the viewpoint of further improving the barrier function of the skin. From the viewpoint of good elongation at the time of coating, it is preferably 6.0% by mass or less, more preferably 5.0% by mass or less, and further preferably 4.0% by mass or less.
  • the pH of the external preparation for skin of the present invention is 7.0 or less, preferably 6.5 or less, more preferably 6.0 or less, from the viewpoint of adjusting the pH environment of normal skin and improving the stability of the component (D). Also, from the viewpoint of reducing skin irritation, it is 4.0 or more, preferably 4.2 or more, and more preferably 4.4 or more.
  • the external preparation for skin of the present invention contains a steroidal anti-inflammatory agent as the component (D)
  • its pH is preferably 5.5 or less, more preferably 5.0 or less, and further, from the viewpoint of the stability of the component (D). It is preferably 4.8 or less, preferably 4.0 or more, more preferably 4.2 or more, still more preferably 4.4 or more, from the viewpoint of storage stability in an emulsified state.
  • the external preparation for skin of the present invention contains heparinoid as the component (D)
  • its pH is preferably 7.0 or less, more preferably 6.5 or less, still more preferably 6.0 or less from the viewpoint of storage stability in an emulsified state. From the same viewpoint, it is preferably 4.0 or more, more preferably 4.5 or more, and further preferably 5.0 or more.
  • the external preparation for skin of the present invention is applied to the skin by containing the components (A) to (E) in a predetermined ratio, and the water evaporates to form a dry film having a lamellar structure on the skin surface.
  • the lamellar structure can be confirmed by wide-angle X-ray diffraction, a polarizing microscope, or the like.
  • A One or more selected from aliphatic alcohols having 14 to 20 carbon atoms
  • B Two or more selected from polyhydric alcohol fatty acid ester type nonionic surfactants
  • C N-acylamino acids, N-acyl One or more selected from taurine and their salts, and phospholipids
  • D One or more selected from steroidal anti-inflammatory agents, non-steroidal anti-inflammatory agents and heparinoids
  • E Water
  • ⁇ 3> The skin external preparation according to ⁇ 1> or ⁇ 2>, wherein the component (A) is a combination of two or more compounds having different carbon atoms.
  • the mass ratio (a1) / (a2) of (a1) the fatty alcohol having 14 or more and less than 18 carbon atoms to the fatty alcohol having 18 or more and 20 or less carbon atoms is preferably 0.1 or more, more preferably 0.6 or more.
  • the skin external preparation according to ⁇ 3> which is more preferably 1.0 or more, preferably 7.0 or less, more preferably 5.0 or less, still more preferably 3.0 or less.
  • the content of the component (A) is preferably 0.3% by mass or more, more preferably 0.5% by mass or more, further preferably 0.8% by mass or more, and preferably 3.0% by mass or less, more preferably 2.5% by mass or less.
  • the component (B) is sucrose fatty acid ester, glycerin fatty acid ester, polyglycerin fatty acid ester, monofatty acid sorbitan, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene sorbit fatty acid ester, polyoxyethylene glycerin fatty acid ester, polyoxyethylene.
  • the skin external preparation according to any one of ⁇ 1> to ⁇ 5>, which is a combination of two or more selected from fatty acid SL, polyoxyethylene hydrogenated castor oil, and the like.
  • the component (B) is one or more polyhydric alcohol fatty acid esters having (b1) HLB of 3 or more and 7 or less, preferably 4 or more and 6 or less, and (b2) HLB of 11 or more and 16, preferably 13 or more. It is composed of one or more polyhydric alcohol fatty acid esters having a mass ratio of 15 or less, and their mass ratios (b1) / (b2) are preferably 0.25 or more, more preferably 0.4 or more, still more preferably 0.6 or more, and also.
  • the external preparation for skin according to any one of ⁇ 1> to ⁇ 6>, which is preferably 4.0 or less, more preferably 2.0 or less, and further preferably 1.0 or less.
  • the content of the component (B) is preferably 0.5% by mass or more, more preferably 1.0% by mass or more, further preferably 1.5% by mass or more, and preferably 5.0% by mass or less, more preferably 4.0% by mass or less.
  • the mass ratio (A) / (B) of the component (A) to the component (B) is preferably 0.35 or more, more preferably 0.4 or more, and preferably 1.5 or less, more preferably 1.0 or less, still more preferably.
  • the acyl amino acid and the acyl group of the acyl taurine are preferably a fatty acid having a saturated or unsaturated linear or branched chain or a mixed fatty acid thereof, and more preferably a mixed fatty acid of a linear fatty acid or a linear fatty acid.
  • the number of carbon atoms thereof is preferably 6 or more, more preferably 10 or more, still more preferably 12 or more, and preferably 22 or less, more preferably 20 or less, still more preferably 18 or less.
  • the skin external preparation according to any one of ⁇ 1> to ⁇ 9>.
  • the acyl amino acid of the component (C) or a salt thereof is preferably one selected from N-stearoyl glutamic acid, N-lauroyl glutamic acid, N-myristoyl glutamic acid, N-cocoyl glutamic acid, N-palm fatty acid glutamic acid and N-lauroyl aspartic acid.
  • the acyltaurine of component (C) or a salt thereof is preferably coconut oil fatty acid methyltaurine, N-caproylmethyltaurine, N-lauroylmethyltaurine, N-myristoylmethyltaurine, N-palmitoylmethyltaurine, N-stearoylmethyltaurine.
  • the phospholipid of component (C) is preferably one or more selected from lecithin, hydrogenated lecithin, lecithin hydroxide, phosphatidylethanolamine, phosphatidylserine, phosphatidylcholine, phosphatidylinositol, phosphatidylglycerol, cardiolipin, sphingomyelin, serabroside, and ganglioside.
  • the skin external preparation according to any one of ⁇ 1> to ⁇ 12>, more preferably hydrogenated lecithin, and even more preferably soybean hydrogenated lecithin.
  • Item 2 The external preparation for skin according to any one of ⁇ 1> to ⁇ 13>, wherein the component (C) is preferably one or more selected from sodium N-acylglutamate, sodium N-acylmethyltaurine and hydrogenated lecithin. ..
  • the content of the component (C) is preferably 0.2% by mass or more, more preferably 0.3% by mass or more, and preferably 0.8% by mass or less, more preferably 0.6% by mass or less ⁇ 1> to ⁇ 14.
  • the external preparation for skin according to any one of the above items.
  • the mass ratio (A) / (C) of the component (A) to the component (C) is preferably 1.0 or more, more preferably 1.5 or more, still more preferably 2.0 or more, and preferably 15 or less, more preferably.
  • the content of the component (D) is preferably 0.025% by mass or more, more preferably 0.05% by mass or more, further preferably 0.1% by mass or more, and preferably 6.5% by mass or less, more preferably 6.0% by mass or less.
  • the content of the component (F) is preferably 1.0% by mass or more, more preferably 1.5% by mass or more, further preferably 2.0% by mass or more, and preferably 6.0% by mass or less, more preferably 5.0% by mass or less.
  • the skin external preparation according to ⁇ 20> which is more preferably 4.0% by mass or less.
  • the pH of the external preparation for skin is preferably 5.5 or less, more preferably 5.0 or less, further preferably 4.8 or less, and preferably 4.0 or more, more preferably.
  • the external preparation for skin according to any one of ⁇ 1> to ⁇ 21>, which is 4.2 or more, more preferably 4.4 or more.
  • the pH of the external preparation for skin is preferably 7.0 or less, more preferably 6.5 or less, further preferably 6.0 or less, and preferably 4.0 or more, more preferably.
  • Examples 1 to 16 Comparative Examples 1 to 5 Prepare the external preparations for skin shown in Tables 1 to 3, and follow the methods and criteria below to "suppress allergen permeation,””drugstability,””emulsificationstability,””smoothness during application,” and “at the time of application. “Good growth” was evaluated.
  • the amount of dye permeated through the dried composition was quantified 3 to 4 times for each composition using a densitometer, and the amount of dye permeation when no coating was set to 1 was expressed as a percentage and evaluated according to the following criteria. did. A: Less than 20% B: 20% or more and less than 40% C: 40% or more and less than 60% D: 60% or more and less than 80% E: 80% or more

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