WO2006090824A1 - Composition de gel et procédé de fabrication idoine - Google Patents

Composition de gel et procédé de fabrication idoine Download PDF

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Publication number
WO2006090824A1
WO2006090824A1 PCT/JP2006/303391 JP2006303391W WO2006090824A1 WO 2006090824 A1 WO2006090824 A1 WO 2006090824A1 JP 2006303391 W JP2006303391 W JP 2006303391W WO 2006090824 A1 WO2006090824 A1 WO 2006090824A1
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WIPO (PCT)
Prior art keywords
gel composition
polymer
acid
mass
acid anhydride
Prior art date
Application number
PCT/JP2006/303391
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English (en)
Japanese (ja)
Inventor
Tomoya Nihei
Runa Unagami
Kazuhiko Matsuda
Yoshifumi Yamagata
Hajime Gotoh
Takeyuki Asanuma
Narumi Tagaki
Yasunori Sakamoto
Original Assignee
Lion Corporation
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Publication of WO2006090824A1 publication Critical patent/WO2006090824A1/fr

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Classifications

    • 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
    • A61K9/7023—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms
    • A61K9/703—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms characterised by shape or structure; Details concerning release liner or backing; Refillable patches; User-activated patches
    • A61K9/7038—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer
    • A61K9/7046—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds
    • A61K9/7053—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds obtained by reactions only involving carbon to carbon unsaturated bonds, e.g. polyvinyl, polyisobutylene, polystyrene
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
    • A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
    • A61L15/22—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons containing macromolecular materials
    • A61L15/24—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
    • A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
    • A61L15/42—Use of materials characterised by their function or physical properties
    • A61L15/58—Adhesives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
    • A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
    • A61L15/42—Use of materials characterised by their function or physical properties
    • A61L15/60—Liquid-swellable gel-forming materials, e.g. super-absorbents

Definitions

  • the present invention relates to a gel composition that can be used as a base for medical patches, wound dressings, taping agents, etc., a patch obtained by spreading the gel composition on a support, and the gel composition It relates to manufacturing methods. More specifically, the present invention relates to a gel composition having high adhesiveness to the skin or mucous membrane and having an excellent gel forming ability.
  • the method of administering a drug by the transdermal and transmucosal absorption route is that the effective concentration of the active ingredient in the body fluid is maintained and can be expected to be sustained immediately, and the absorption of the active ingredient Increased interest in recent years due to easy adjustment of speed, low risk of side effects, and effective use of medicinal ingredients that are less affected by stomach acid, digestive enzymes, etc., and less affected by metabolism due to the first-pass effect of the liver. ing.
  • a poultice prepared by adding a water-soluble polymer such as sodium polyacrylate or carboxybule polymer to water, SIS, Tapes with a plasticizer and tackifier added to rubber, silicon and acrylic polymers such as polyisobutylene, plaster agents, oily bases such as liquid paraffin and petrolatum, water absorption such as gelatin and sodium carboxymethylcellulose Ointment bases containing functional polymers are known.
  • a water-soluble polymer such as sodium polyacrylate or carboxybule polymer
  • SIS Tapes with a plasticizer and tackifier added to rubber
  • silicon and acrylic polymers such as polyisobutylene
  • plaster agents oily bases such as liquid paraffin and petrolatum
  • water absorption such as gelatin and sodium carboxymethylcellulose Ointment bases containing functional polymers
  • a hydrophilic polymer such as polyacrylic acid and carboxymethyl cellulose and water, one selected from the group consisting of rosin ester, hydrogenated petroleum resin, and terpene-based resin Medical patch containing the above tackified rosin (see Patent Document 1) ),
  • a pressure-sensitive adhesive composition containing a polymer soluble in a lower alcohol and having a carboxyl group or a salt thereof, a lower alcohol, a polyhydric alcohol, and metal sulphate, and gelled see Patent Document 2
  • Adhesive gel base using methyl vinyl ether maleic anhydride copolymer or methyl vinyl ether maleic acid copolymer as the base polymer, polyfunctional epoxy compound as the cross-linking agent, and gelling water and polyhydric alcohol (Patent Literature) 3) has been proposed.
  • these bases contain water or lower alcohol having a relatively low boiling point as the main component, water or lower alcohol evaporates during use, resulting in performance such as stickiness and skin irritation
  • anhydrous gel matrix having a hydroxyl group and a Z or carboxyl group in the molecule using a cross-linking agent and gelling the polyhydric alcohol with a polyhydric alcohol-soluble polymer see Patent Document 4
  • a non-aqueous patch in which a polyhydric alcohol is gelled with a polyhydric alcohol-soluble polymer and a strong ropoxyvinyl polymer has also been proposed.
  • a non-aqueous thermal gel composition (see Patent Document 6) characterized by containing a polyhydric alcohol and a power that dissolves in the polyhydric alcohol or a polymer that swells with the polyhydric alcohol has also been proposed. ing. Since the main component of this base is a polyhydric alcohol, the essential components that hardly deteriorate with time are a polyhydric alcohol and a polymer, and it is expected that the manufacturing operation is simple. However, there are cases where the adhesiveness and gel-forming ability are insufficient, with no mention of adhesiveness and gel-forming ability.
  • Patent Document 1 Japanese Patent Laid-Open No. 6-254150
  • Patent Document 2 Japanese Patent Laid-Open No. 9-143062
  • Patent Document 3 Japanese Patent Laid-Open No. 9-286891
  • Patent Document 4 Japanese Patent Laid-Open No. 63-203162
  • Patent Document 5 Japanese Patent Laid-Open No. 2003-113077
  • Patent Document 6 Japanese Patent Laid-Open No. 2001-245913 Disclosure of the invention
  • the present invention provides a gel composition having high adhesion to skin or mucous membrane and having an excellent gel-forming ability, a patch using the gel composition, and a method for producing the gel composition.
  • the purpose is to do.
  • the present inventors have found that a polymer and a polyhydric alcohol in which the acid anhydride portion and the corresponding acid compound portion in the polymer are in a specific range.
  • the inventors have found that a gel composition having high adhesion to the skin or mucous membrane and having an excellent gel forming ability can be obtained, and the present invention has been completed.
  • the present invention comprises (A) a repeating unit composed of at least one unsaturated portion and an acid anhydride portion, and at least one unsaturated portion and an acid compound portion corresponding to the acid anhydride portion.
  • a gel composition comprising a polymer containing a repeating unit, and (B) a polyhydric alcohol,
  • the gel composition is characterized in that the polymer contains an acid anhydride portion and an acid compound portion corresponding to the acid anhydride portion in a molar ratio of 15Z85 to 85Z15.
  • the present invention also provides a patch in which the gel composition is spread on a support.
  • the present invention also includes (a) hydrolyzing a polymer containing a repeating unit composed of at least one unsaturated portion and an acid anhydride portion, and an acid anhydride portion contained in the polymer.
  • a repeating unit composed of at least one unsaturated portion and an acid anhydride portion wherein the acid compound portion corresponding to the acid anhydride portion is a molar ratio of 15Z85 to 85Z15, Obtaining a polymer comprising a repeating unit composed of at least one unsaturated moiety and an acid / acid compound moiety corresponding to the acid anhydride moiety,
  • a method for producing a gel composition is provided.
  • the invention's effect is provided.
  • the present invention it is possible to provide a gel composition having high adhesion to the skin or mucous membrane and having an excellent gel forming ability. According to the present invention, it is also possible to provide a gel composition that hardly causes skin irritation with a small deterioration power S of performance.
  • an external preparation composition such as a patch excellent in transdermal absorbability of a medicinal component, preferably excellent in initial transdermal absorbability.
  • the gel composition of the present invention is excellent in solubility of medicinal components, particularly medicinal components that are difficult to absorb percutaneously, and can provide an external preparation composition with an increased amount of medicinal components.
  • the gel composition of the present invention also has good usability and can be applied to various preparations.
  • the polymer (A) used in the present invention has a mono ktt force of 15/85 to 85/15, preferably 15/85 of an acid anhydride portion and an acid compound portion corresponding to the acid anhydride portion. -80/20, more preferably 20Z80-70Z30. Within such a range, it is preferable because it has both high adhesiveness and excellent gel forming ability. If the ratio of the acid anhydride is too high, it becomes difficult to obtain a gel composition having both high tackiness and excellent gel-forming ability. If the ratio of the acid compound portion is too high, the gel composition has excellent gel-forming ability. It becomes difficult to obtain a gel composition.
  • the molar ratio between the acid anhydride and the acid compound portion corresponding to the acid anhydride portion can be measured by potentiometric titration.
  • the polymer has the same number of moles of at least one unsaturated portion as the sum of the number of moles of the acid anhydride portion and the number of moles of the acid compound portion corresponding to the acid anhydride portion. I like it.
  • the weight average molecular weight of the (ii) polymer of the present invention is preferably high enough to obtain good gel-forming ability, for example, 10,000 to 10,000,000, preferably 100,000 to 5,000,000. This average molecular weight is a value measured by a size exclusion separation low angle laser light scattering detector method.
  • the blending amount of the polymer with respect to the gel composition of the present invention is, for example, 1 to 55 quality. The amount is preferably 1 to 40% by mass, more preferably 1 to 30% by mass.
  • At least one unsaturated portion is a beluie compound.
  • the vinyl compound include methyl vinyl ether, styrene, ethylene, isobutylene and the like. Of these, methyl beryl ether is preferred.
  • the acid anhydride portion is preferably selected from the group strength of maleic anhydride portion and itaconic anhydride partial force. More preferably, (A) the polymer is an alkyl butyl ether having 3 to 24 carbon atoms, a maleic anhydride, a maleic anhydride, a maleic acid copolymer, an alkyl bulle ether having 3 to 24 carbon atoms, and itaconic anhydride. Z-taconic acid power Constructed copolymer power is selected. More preferred are a copolymer composed of methyl vinyl ether Z maleic anhydride Z maleic acid and a copolymer composed of methyl vinyl ether Z itaconic anhydride Z itaconic acid. Of these, a copolymer composed of methyl vinyl ether Z maleic anhydride and maleic acid is most preferred.
  • the (A) polymer of the present invention includes, for example, a monomer containing at least one unsaturated moiety, a monomer containing an acid anhydride moiety, and a monomer containing an acid compound moiety corresponding to the acid anhydride moiety. It can also be produced by copolymerization or (a) by hydrolysis of a polymer containing a repeating unit composed of at least one unsaturated moiety and an acid anhydride moiety.
  • a) polymer for example, those commercially available from ISP as GA NTREZ AN series can be used.
  • Hydrolysis is performed, for example, on (a) 100 parts by mass of polymer, 2 to: LOO parts by mass, preferably 2 to 50 parts by mass of water, and at a temperature of 20 to 100 ° C. for 1 to 600 minutes, This can be done by reacting.
  • the polymer may be dissolved in a solvent such as acetone, tetrahydrofuran, dimethyl sulfoxide, dimethylformamide in advance, and water may be added thereto, or water may be sprayed onto the polymer.
  • the polymer may be absorbed as water vapor.
  • the gel composition of the present invention is formulated into a patch or the like, it is possible to reduce the degree to which the adhesiveness or the like decreases with time during use.
  • the obtained polymer can be used as it is, or it can be used after removing water present in the system to about 1% with respect to the polymer by heating, drying under reduced pressure or the like.
  • the polyhydric alcohol used in the present invention preferably does not evaporate during use.
  • Glycerin, triglycerin, polyglycerin, polyethylene glycol, dipropylene glycol, triethylene glycol, polyethylene glycol monourea (weight average molecular weight 200-2000, preferably 200-600), positive P-pilling !; 3— (weight Average molecular weight 400-4000, preferably 400-1000), polyethylene 'polypropylene monole (weight average molecular weight 1000-6000, preferably ⁇ 1000-3000), positive aged hydrogenated castor oil (5E.O.-100E) O., preferably 10E. O. to 60E. O.) and sorbitol, etc., and these may be used alone or in combination of two or more. Can be used in appropriate combinations.
  • the weight average molecular weight is 200 to 2000, more preferably 200 to 1500, more preferably ⁇ is 200 to 1000, and particularly preferably ⁇ is 200 to 600.
  • polyethylene glycol it is particularly preferable to use a polyvalent alcohol other than polyethylene glycol because the transdermal absorbability of the medicinal component is improved.
  • polyhydric alcohols other than polyethylene glycol include dihydric alcohols such as ethylene glycol, propylene glycol, 1,3-butylene glycol, diethylene glycol and dipropylene glycol, and trivalent alcohols such as glycerin and trimethylolpropane.
  • dihydric alcohols such as ethylene glycol, propylene glycol, 1,3-butylene glycol, diethylene glycol and dipropylene glycol.
  • dihydric alcohols such as ethylene glycol, propylene glycol, 1,3-butylene glycol, diethylene glycol and dipropylene glycol.
  • it is preferably used as a dihydric or hexahydric polyhydric alcohol mixture containing polyethylene glycol having a weight average molecular weight of 200 to 2000! /.
  • the mixing ratio of polyethylene glycol and divalent to 6-valent polyhydric alcohols other than polyethylene glycol is 1: 9-: LO: 0 is preferred by mass ratio 1: 9-9: 1 is more preferred 2 : 8-8: 2 is more preferable.
  • LO: 0 is preferred by mass ratio 1: 9-9: 1 is more preferred 2 : 8-8: 2 is more preferable.
  • the measuring method of the weight average molecular weight of the polyhydric alcohol which is a polymer can be measured by a titration test described in the cosmetic raw material standards.
  • the blending amount of the polyhydric alcohol with respect to the gel composition of the present invention is, for example, 40 It is 50 mass%-99 mass%, Preferably, it is 50 mass%-99 mass%, More preferably, it is 60 mass%-99 mass%. Further, the total amount of the polymer (A) and the polyvalent alcohol in the gel composition of the present invention is, for example, 60% by mass or more, preferably 65% by mass or more, and more preferably 70% by mass or more. Hope U ,.
  • the mass ratio of the polymer (A) of the present invention to the polyhydric alcohol is 1Z99 to 55Z45, preferably 1Z99 to 45Z55, and more preferably 1Z99 to 35Z65.
  • the gel composition of the present invention may optionally contain a polymer that dissolves or swells in the polyhydric alcohol used.
  • dissolution means that a polyvalent alcohol solution of 1% by mass of a polymer becomes uniform.
  • Swelling refers to a state in which a polymer absorbs polyhydric alcohol and increases its volume when mixed with a certain mass of polyhydric alcohol, and the mass of this polyhydric alcohol mixture is the polymer before mixing. This is when the mass is twice or more.
  • the polymer is preferably gelled by dissolving or swelling in a polyhydric alcohol.
  • the gel composition of the present invention may optionally contain additives such as pressure-sensitive adhesives, binders, medicinal ingredients, transdermal absorption enhancers, other active ingredients, perfumes, and pigments. It is preferable to contain at least one selected from the group consisting of a pressure-sensitive adhesive, a binder, and a mixture thereof because the pressure-sensitive adhesiveness of the gel composition of the present invention can be improved. Further, when the gel composition of the present invention contains a medicinal component, it is preferable because the medicinal effect can be sustained. When the transdermal absorption enhancer is contained, the gel composition of the present invention contains a medicinal component. It is preferable because the percutaneous absorbability of the medicinal component, particularly the initial percutaneous absorbability, is improved.
  • the additive used in the present invention is not particularly limited as long as it can be dissolved or dispersed in a polyhydric alcohol.
  • active ingredients include warm sensation active ingredient, cool sensation active ingredient, terminal circulation promoting agent, anti-inflammatory analgesic ingredient, blood circulation promoter, local anesthetic agent, antiperspirant, athlete's foot drug, antibacterial / bactericidal ingredient, Antibacterial and sterilizing agents, whitening ingredients, sebum suppressants, keratolytic agents, active ingredients for cervical sprains, and astringent ingredients. These can be used alone or in combination of two or more.
  • Adhesives such as rosin ester, alicyclic resin, and polyterpene resin are mixed with elastomers such as styrene Z isoprene Z styrene block copolymer (SIS) and polyisobutylene (PIB).
  • Rubber adhesives acrylic adhesives such as polyacrylic acid, polyacrylate (preferably sodium salt), acrylic acid Z methacrylic acid copolymer; silicone adhesives such as polysiloxane derivatives; alkyl Examples include vinyl ether-based adhesives such as vinyl ether Z maleic anhydride copolymer; and butyl acetate-based adhesives such as acrylic ester Z vinyl acetate copolymer.
  • These pressure-sensitive adhesives may be used alone or in combination of two or more. Acrylic adhesives and vinyl ether adhesives are more preferably used.
  • the mass average molecular weight of the pressure-sensitive adhesive is preferably 10,000 to 10,000,000, more preferably 10,000 to 50,000,000!
  • the blending amount of the pressure-sensitive adhesive is preferably 1 to 78% by mass, more preferably 5 to 75% by mass in the composition. If it is at least the lower limit of the range, sufficient adhesion to the use site of the gel composition is obtained, and if it is at most the upper limit, the peelability of the use site force of the gel composition is good.
  • binder examples include carboxyvinyl polymer, alginic acid, polybutyl alcohol, polyvinyl pyrrolidone, carboxymethyl cellulose, hydroxypropyl cellulose, hydroxypropyl methyl cellulose and the like. Among these, carboxyvinyl polymer and hydroxypropylcellulose are preferred, and hydroxypropylcellulose is more preferred.
  • the weight average molecular weight of the binder is preferably 10,000 to 100,000,000, more preferably 50,000 to 5,000,000.
  • the weight average molecular weight of the binder is
  • It can be measured by gel permeation chromatography method or light scattering method.
  • a value converted into polyethylene oxide by gel permeation chromatography method and in the case of hydroxypropyl cellulose, gel permeation.
  • gel permeation Use the value calculated by pullulan conversion by the Chillon chromatography method, or the value measured by the light scattering method in the case of polybulurpyrrolidone.
  • binders may be used alone or in combination of two or more.
  • the blending amount of the binder is preferably 1 to 30% by mass and more preferably 1 to 20% by mass in the composition. If it is this range, the retention property of the composition in the applied part will become favorable, and the sustainability of a medicinal effect can be improved.
  • the blending amount of the mixture is preferably 1 to 78% by mass, more preferably 5 to 75% by mass in the composition.
  • the medicinal properties include non-steroidal anti-inflammatory drugs such as indomethacin, fuel binac, ketoprofen, flurbiprofen, diclofenac, and ester derivatives thereof; antihistamines such as diphenhydramine, central nervous system drugs such as isoprenaline hydrochloride, estradiol and testosterone Hormonal agents; analgesics such as aspirin, acetaminophen, ibuprofen; antiarrhythmic agents such as disopyramide phosphate; coronary vasodilators such as tolazoline hydrochloride; local anesthetics such as lidocaine; muscle relaxants such as skisamethonium chloride; Antifungal agents such as clotrimazole, anti-neoplastic agents such as fluorouracil, dysuria such as tamsulosin hydrochloride, antiepileptic agents such as diazepam, antiparkinsonian agents such as bromocriptine me
  • the active ingredients for warm feeling include, for example, red pepper extract, red pepper tincture, kabusaicin, Twilight extract, meat katsura, ginger extract, ginger alcohol extract, cantalis tincture
  • Nicotinic acid benzyl ester vitamin E, borneol, dl-camphor, 1-menthol, heart force oil, eucalyptus oil, methyl salicylate, glycol salicylate, ⁇ ⁇ -allyl alcohol derivatives, ⁇ -rilamide of norlate, vanillyl
  • Examples include alcohol alkyl ethers, pepper family plant extracts, sage genus plant extracts, argentia genus plant extracts, clove oil, and eugenol derivatives. When these components are added, blood circulation can be promoted using a local or induced stimulus to the skin, and a warm feeling can be obtained.
  • Active ingredients for cooling sensation include, for example, menthol, menthol glycerol ether, and derivatives of these compounds such as esters, N-ethyl-p-3-menthane-carboxamide, heart force oil, and force flu.
  • menthol menthol glycerol ether
  • derivatives of these compounds such as esters, N-ethyl-p-3-menthane-carboxamide, heart force oil, and force flu.
  • the peripheral circulation promoting agent includes, for example, tocolol acetate.
  • Anti-inflammatory analgesic components include, for example, salicylic acid, methyl salicylate, glycol salicylate, diphenhydramine, chlorfelamamine maleate, ammonium glycyrrhizinate, dicalium glycyrrhizinate, glycyrrhizic acid, stearyl glycyrrhizinate, 13-darlicylretinoic acid, , Azulene, ⁇ -aminocaproic acid, hydrocortisone, calcium pantothenate, ethyl pantothenate, hydrocortisone acetate, nor-hydroxamide, diphenol hydramine, indomethacin, ketoprofen, flurbiprofen, ibuprofen, suprofen, Loxoprofen, Zaltoprofen, Piroxicam, Fuerbinac, Arnica
  • Examples of the blood circulation promoter include senpri extract, cephalanthin, vitamin ⁇ and its derivatives, ⁇ oryzanol, peppermint oil, turpentine oil, thiodi oil, geraol oil, thymol oil, wikiyou oil, bergamot oil, anise Oil, Lavender oil, Black pepper oil, Beninona oil, Anole extract, Maronier extract, Enmeiso extract, Bodaige extract, Melissa extract, ⁇ ethyl ⁇ -3-menthane monocarboxamide, etc.
  • Examples of local anesthetics include funnel extract, jib force-in, pro force-in, and lidocaine.
  • Tannin-containing components are preferably used as the brick component.
  • An inorganic salt is preferably used as the perspiration promoter.
  • calcined gypsum calcium chloride, anhydrous calcium chloride, magnesium chloride, anhydrous magnesium chloride, calcium carbonate, anhydrous calcium carbonate, sodium sulfate, anhydrous sodium sulfate, magnesium sulfate, anhydrous magnesium sulfate, sodium hydroxide, potassium hydroxide
  • Sterilization ⁇ Antibacterial components include, for example, pyrotatone olamine, cyclopilotas olamine, benzalkonium chloride, benzethonium chloride, halocarban, clohexhexidine hydrochloride, zinc pyrithione, phenol, trichlorocarba -Lido, chlorhexidine dalconate, cetyl pyridinium chloride, isopropylmethylphenol, allantoin, anti-plasmin agent ( ⁇ -aminocaproic acid, tranexamic acid), dihydrocholesterol, tonic extract, force mitre (containing azulene), There are essential oils such as eucalyptus oil and hinokitiol.
  • quinuhada Callophyllis flabellulata
  • water extract which is an active ingredient, miconazole nitrate, and other antipruritic agents, diphenhydramine hydrochloride, chlorfelamine maleate, camphor, and labrite are used.
  • Antibacterial 'bactericidal agents include, for example, zinc pyrithione, trichlorocarbalide, triclosan, aloe extract, carrot extract, licorice extract, wolverine extract, force extract, birch extract, water-soluble cerium salt, abietic acid, pimaric acid, Sulfur containing bis (2-pyridinethiol 1 oxide) zinc, pyridinethione salt, histamine 2 receptor antagonist, vitamin E acetate, pantothruethyl ether, citrate triethyl ester, methionine, cystine, cysteine, etc.
  • a whitening component, a sebum inhibitor, a keratolytic agent, and the like can be used mainly when used as a cosmetic.
  • Whitening ingredients include, for example, arbutin, ellagic acid, kojic acid, hydroquinone, vitamin C, placenta extract, titanium oxide, water extract of Callophyllis japonica, and water extract of Callophyllis adhaerens. There is.
  • sebum inhibitors and keratolytic agents examples include estradiol, estrone, ethynylestradiol, vitamin B6, io, resorcin, benzalkonium chloride, benzethonium chloride, halocarban, 2, 4, 4 —Trichrome mouthpieces 2-hydroxyphenol, selenium sulfide, pentadecanoic acid, pentadecanoic acid derivatives, various vitamins, etc.
  • non-steroid anti-inflammatory agents such as indomethacin, fuerbinac, ketoprofen, flurbiprofen, diclofenac and the like, which are preferably poorly water-soluble medicinal ingredients because the effects of the present invention are particularly remarkable; estradiol, testosterone, etc.
  • Hormonal agents, antihypertensive agents such as furosemide and clonidine, vasodilators such as nitroglycerin and isosorbide nitrate, smoking cessation aids such as nicotine, bronchodilators such as lolobtail, scopolamine and fentanyl are more preferred. More preferred are indomethacin, fuel binac, ketoprofen and flurbiprofen.
  • These medicinal ingredients may be used alone or in combination of two or more.
  • “poorly water-soluble medicinal ingredient” is an index of sparingly soluble, for example, when it shows solubility in water according to the Japanese pharmacy property test, “very insoluble!” Or “almost insoluble! /, "The medicinal ingredient for which the term” is used.
  • the compounding amount of the medicinal component in the gel composition of the present invention can be appropriately set by those skilled in the art, and is preferably about 0.05 to 70% by mass in the composition.
  • R 1 is a hydrocarbon group having 3 to 36 carbon atoms
  • R 2 is a hydrocarbon group having 1 to 20 carbon atoms
  • R 3 is a hydrogen atom or —COOR 4 and R 4 is 1 carbon atom.
  • ⁇ It is a hydrocarbon group of L0.
  • the ester represented by these is mention
  • R 1 represents a hydrocarbon group having 3 to 36 carbon atoms, preferably 4 to 20 carbon atoms, which may be linear, branched or saturated or unsaturated. Good. A carbon number in this range is preferable because it is excellent in transdermal absorbability of medicinal ingredients and solubility in polyhydric alcohols including polyethylene glycol.
  • R 3 is a hydrogen atom
  • the number of carbon atoms is preferably 10 to 36.
  • COOR 4 is selected, the number of carbon atoms is preferably 3 to 20.
  • R 2 represents a hydrocarbon group having 1 to 20 carbon atoms, preferably 1 to 18 carbon atoms, which may be linear, branched or saturated or unsaturated. Good.
  • R 3 is a hydrogen atom, the number of carbon atoms is preferably 1-18.
  • R 3 is one COOR 4, the number of carbon atoms is preferably from it preferably instrument is 1-10 1-6, more preferably 1-3.
  • R 3 represents a hydrogen atom or COOR 4 and R 4 represents a hydrocarbon group having 1 to 10 carbon atoms, preferably 1 to 8 carbon atoms, and the hydrocarbon group may be linear or branched. It may be saturated or unsaturated.
  • R 2 and R 4 may be the same as or different from each other.
  • transdermal absorption enhancer examples include decyl sebacate, diisopropyl sebacate, decyl adipate, diisopropyl adipate, oleyl oleate, isopropyl myristate, isopropyl palmitate, ethyl linoleate, isopropyl linoleate. And the like. Of these, decyl sebacate, diisopropyl sebacate, diisopropyl adipate, oleyl oleate, and isopropyl myristate are preferred. Especially preferred is Jetyl Sebacate! /.
  • transdermal absorption enhancers may be used alone or in combination of two or more.
  • the blending amount of the transdermal absorption enhancer is preferably 1 to 50% by weight in the composition, 3 to 40% by weight, more preferably 5 to 30% by weight, and even more preferably 10 to 30% by weight. preferable. Within such a range, the transdermal absorbability of the medicinal component is good.
  • the mixing ratio of the polyhydric alcohol and the transdermal absorption enhancer is preferably 1: 9 to 9: 1 in terms of mass ratio, more preferably 2: 8 to 8: 2. Within this range, both the solubility of the medicinal component and the transdermal absorbability of the medicinal component are excellent.
  • transdermal absorption enhancer examples include crotamiton and benzyl alcohol, and these can be used singly or in appropriate combination of two or more.
  • fragrances include amylcinnamic aldehyde, benzyl acetate, p-tert butynolecyclohexenole acetate, cyclaset, cyclaprop, garaki solid, bedeon, orange oil and the like.
  • the dye is not particularly limited, and the dyes described in the Legal Dye Handbook can be blended. For example, Red 2, Green 3, Blue 1, Dai 402, Yellow 401, Purple 401, etc. is there.
  • the gel composition of the present invention can be produced by dissolving (A) a polymer in (B) a polyhydric alcohol, and performing a crosslinking reaction with the polyhydric alcohol to form a gel.
  • a crosslinking reaction with the polyhydric alcohol to form a gel.
  • the heating may be performed while kneading or kneading (A) the polymer and (B) the polyhydric alcohol.
  • the slurry containing (A) the polymer and (B) the polyhydric alcohol is made into a nonwoven fabric or the like.
  • the heating temperature is different depending on the (B) polyhydric alcohol used.
  • (B) In the range not exceeding the boiling point of the polyhydric alcohol, for example, about 20 ° C to 250 ° C, preferably 40 ° C to It is desirable that the temperature be about 200 ° C, more preferably about 60 ° C to 180 ° C.
  • the heating time is, for example, 10 minutes to 10 hours, preferably 30 minutes to 4 hours.
  • the gel composition of the present invention is not particularly limited in its use and dosage form.
  • it is used as an external preparation composition that can be applied to skin, hair, oral cavity (including mucous membranes), nails and the like.
  • the dosage form is not particularly limited, and includes patches (medical patches, wound dressings, tabing agents, foot care sheet agents, knock agents, mask agents), ointments, gels, and coating agents.
  • a patch is preferred.
  • the coating amount of the external preparation composition is preferably about 0.01 to about Lg / cm 2 , for example, depending on the types of medicinal ingredients and binders used.
  • the composition for external use can be produced by a conventional method.
  • the patch is obtained by spreading the gel composition on a support
  • the spreading method is not particularly limited, and can be performed using a known apparatus, for example, a roll coater.
  • a knife coater, a slit die coater, a gravure coater or the like can be used.
  • a support body a well-known thing can be used, For example, paper, a knitted fabric, a woven fabric, a nonwoven fabric, a polymer film, or those laminated bodies etc. can be mentioned.
  • Materials for knitted fabric, woven fabric, non-woven fabric, and polymer film include polyester, polypropylene, rayon, Examples include butyl chloride, polyethylene, polyurethane, and polyurethane 'vinyl chloride copolymer film.
  • the amount of spreading when the gel composition is spread on the support is not particularly limited, and it is 0.001 to 1 lg / cm 2 , preferably 0. 003 to 0.5 g / cm 2 , more preferably 0.005 to 0.2 gZcm 2 .
  • the patch of the present invention after spreading the gel composition, is used as needed for the purpose of preventing volatilization of medicinal ingredients, protecting the adhesive surface, etc.
  • a facing layer may be provided on the top and covered.
  • the facing layer is not particularly limited as long as it can protect the patch, and examples thereof include plastic films such as polypropylene film, polychlorinated bull film, polyethylene film, and polyethylene terephthalate film, and release paper.
  • the patch can then be cut into an appropriate size and used.
  • the cutting method may be any cutting method such as slitting, cutting by push-cutting, or a combination of these, or the punching cutting method.
  • the adhesive patch of the present invention has an adhesive strength adjusted to 4 to 32, preferably 6 to 30, when measured at an inclination angle of 30 °. Is preferred. If it is at least the lower limit of the range, sufficient adhesion to the site of use of the patch can be obtained, and if it is not more than the upper limit, the patch can be peeled off with little skin irritation.
  • the adhesive strength of the patch can be adjusted by selecting the adhesive and controlling the blending amount.
  • Examples 1A to: L 1A, 13A and 14A and Comparative Examples 1A to 4A are gel compositions obtained by kneading each component with a bench-kinder (PNV-1, manufactured by Hitachi, Ltd.) polyester - Tsu DOO such that 0. lgZcm 2 on (Toho Textile Co., Ltd.), and uniformly spread by a roll coater (manufactured by Hanae machinery industry Co.), and the sheet.
  • PNV-1 bench-kinder polyester - Tsu DOO
  • 0. lgZcm 2 on Toho Textile Co., Ltd.
  • a roll coater manufactured by Hanae machinery industry Co.
  • Example 12A is a polyester knit (manufactured by Toho Textile Co., Ltd.), in which each component was kneaded for 5 minutes at room temperature with a bench-top (PNV-1, manufactured by Hitachi, Ltd.). ) Up 0 It was prepared by heating after uniformly coating with a roll coater (manufactured by Kaei Machine Industry Co., Ltd.) so that lgZcm 2 was obtained. The gel forming ability of each gel composition and the adhesiveness of each patch were evaluated by the following methods.
  • the gel composition has a higher gel-forming ability as the storage elastic modulus has a lower frequency dependency. Therefore, the present inventors investigated how much the storage elastic modulus of the prepared gel composition is affected by the change of the measurement frequency, and evaluated the gel forming ability.
  • the storage elastic modulus was measured with a stress-controlled rheometer (Rheo—Stress RS—100, manufactured by Haake) at 25 ° C, and the storage elastic modulus (G ′ (0. 1)) with a frequency of 0. IradZsec.
  • the gel-forming ability was evaluated from the value of the ratio (G, (10) ZG ′ (0.1)) to the storage elastic modulus (G, (10)) of lOradZ sec.
  • G '(10) ZG' (0.1) is 0.67 or more and less than 1.5 ⁇ ⁇ '', 0.5 or more and less than 0.67, and 1.5 or more and less than 2 is ⁇ ⁇ '', Less than 0.5 and 2 or more were designated as “X”.
  • the produced sheet was evaluated with a texture analyzer (TA-XT2, manufactured by Stable Micro Systems).
  • a probe with a diameter of 20 mm covered with a collagen film was adhered to the sheet with a load of 100 g for 10 seconds, and then the peeling operation when peeling at a peeling speed of lOmmZsec was evaluated as tackiness.
  • the evaluation was “O” for lOOOg'mm or more, “ ⁇ ” for 500g′mm or more and less than 1000 8'111111, and “” for 50 ( ⁇ '111111 or less.
  • Methyl beryl ether Z Maleic anhydride Copolymer (ISP, GAN TREZ AN—139) 100 mass%, 8 mass% water added, 90 ° C [Koo!
  • a copolymer (molecular weight: 1.08 million) composed of methyl vinyl ether Z maleic anhydride Z maleic acid having a molar ratio of maleic anhydride Z maleic acid of 56Z44 was obtained as polymer (A). .
  • Methyl beryl ether Z Maleic anhydride Power copolymer (ISP, GAN TREZ AN—139) 100 mass% of water, 15 mass% of water added, and then hydrolyzed at 90 ° C for 300 minutes.
  • ISP Methyl beryl ether Z Maleic anhydride Power copolymer
  • GAN TREZ AN—139 Methyl beryl ether Z Maleic anhydride Power copolymer
  • Methyl beryl ether Z Maleic anhydride Copolymer (ISP, GAN TREZ AN—169) Add 100 parts by mass of 4 parts by mass of water and hydrolyze at 90 ° C for 180 minutes As a result, a copolymer (molecular weight: 1.98 million) composed of methyl vinyl ether Z maleic anhydride Z maleic acid having a maleic anhydride Z maleic acid molar ratio of 70Z30 was obtained as the polymer (A).
  • Methyl vinyl ether Z Maleic anhydride Copolymer (ISP, GAN TREZ AN—169) Add 100 parts by weight of 3 parts by weight of water and hydrolyze at 90 ° C for 180 minutes As a result, a copolymer (molecular weight: 1.98 million) composed of methyl vinyl ether Z maleic anhydride Z maleic acid having a molar ratio of maleic anhydride Z maleic acid of 74Z26 was obtained as the polymer (A).
  • Methyl vinyl ether Z Maleic anhydride Copolymer (ISP, GAN TREZ AN—169) 100 mass%, add 2 mass% of water, and add 90 ° C.
  • a copolymer (molecular weight 1.98 million) composed of methyl vinyl ether Z maleic anhydride Z maleic acid having a molar ratio of maleic anhydride Z maleic acid of 77Z23 was obtained as (A) polymer. . 20 parts by mass of the obtained (A) polymer and 80 parts by mass of polyethylene glycol (PEG400, manufactured by Lion Corporation) were kneaded at 90 ° C. for 90 minutes, and then spread into a sheet.
  • PEG400 polyethylene glycol
  • Methyl beryl ether Z Maleic anhydride Copolymer (ISP, GAN TREZ AN—169) 100 mass%, 2 mass% of water is added, and 90 o C
  • a copolymer (molecular weight: 1.98 million) composed of methyl vinyl ether Z maleic anhydride Z maleic acid having a molar ratio of maleic anhydride Z maleic acid of 84Z16 was obtained as (A) polymer. .
  • Methyl beryl ether Z Maleic anhydride Powered copolymer (ISP, GAN TREZ AN—139) 100 mass%, 20 mass% of water is added, and 90 ° C [Koo!
  • a copolymer (molecular weight 1.08 million) composed of methyl vinyl ether Z maleic anhydride Z maleic acid having a molar ratio of maleic anhydride to maleic anhydride of 17Z83 is obtained as the polymer (A). Obtained.
  • Methyl beryl ether Z Maleic anhydride Powered copolymer (ISP, GAN TREZ AN—119) 100 mass%, 25 mass% water added, 20 ° C [Koo!
  • a copolymer (molecular weight 210,000) composed of methyl vinyl ether Z maleic anhydride Z maleic acid having a molar ratio of maleic anhydride Z maleic acid of 46Z54 was obtained as polymer (A). .
  • Methyl beryl ether Z Maleic anhydride Power copolymer (ISP, GAN TREZ AN—139) 100 mass% of water, 15 mass% of water added, and then hydrolyzed at 90 ° C for 300 minutes.
  • ISP Methyl beryl ether Z Maleic anhydride Power copolymer
  • GAN TREZ AN—139 Methyl beryl ether Z Maleic anhydride Power copolymer
  • Methyl beryl ether Z Maleic anhydride Power copolymer (ISP, GAN TREZ AN—139) 100 mass%, 15 mass% water added, 90 ° C
  • ISP Methyl beryl ether Z Maleic anhydride Power copolymer
  • GAN TREZ AN—139 Methyl beryl ether Z Maleic anhydride Power copolymer
  • Methyl beryl ether Z Maleic anhydride Power copolymer (ISP, GAN TREZ AN—139) 100 mass%, 15 mass% water added, 90 ° C
  • ISP Methyl beryl ether Z Maleic anhydride Power copolymer
  • GAN TREZ AN—139 Methyl beryl ether Z Maleic anhydride Power copolymer
  • Methyl beryl ether Z Maleic anhydride Copolymer (ISP, GAN TREZ AN—139) 100 mass%, 8 mass% water added, 90 ° C [Koo!
  • (A) the polymer is composed of maleic anhydride Z maleic acid molar ratio 56Z44 methyl vinyl ether Z maleic anhydride Z maleic acid A copolymer (molecular weight 1.08 million) was obtained.
  • Methyl beryl ether Z Maleic anhydride Copolymer (ISP, GAN TREZ AN—139) 100 mass%, 8 mass% water added, 90 ° C [Koo!
  • a copolymer (molecular weight: 1.08 million) composed of methyl vinyl ether Z maleic anhydride Z maleic acid having a molar ratio of maleic anhydride Z maleic acid of 56Z44 was obtained as polymer (A). .
  • the obtained (A) polymer 25 parts by mass, ethylene glycol (manufactured by Kanto Chemical Co., Ltd.) 23 parts by mass, dipropylene glycol (Showa Denko Co., Ltd.) 30 parts by mass, and polyethylene glycol (PEG400, Lion Corporation) 22 parts by mass were kneaded at 90 ° C for 90 minutes, and then spread into a sheet.
  • Methyl beryl ether Z Maleic anhydride Copolymer (ISP, GAN TREZ AN—139) 100 mass%, 8 mass% water added, 90 ° C [Koo!
  • a copolymer (molecular weight: 1.08 million) composed of methyl vinyl ether Z maleic anhydride Z maleic acid having a molar ratio of maleic anhydride Z maleic acid of 56Z44 was obtained as polymer (A). .
  • Methyl beryl ether Z Maleic anhydride Copolymer (ISP, GAN TREZ AN—139) Add 100 parts by weight of 1 part by weight of water and hydrolyze at 90 ° C for 180 minutes As a result, a copolymer having a molar ratio of maleic anhydride Z maleic acid of 87 Z13 and a methyl butyl ether Z maleic anhydride Z maleic acid power (molecular weight 1080,000) was obtained. 15 parts by mass of the obtained polymer and 85 parts by mass of polyethylene glycol (PEG400 Lion Co., Ltd.) were kneaded at 90 ° C. for 90 minutes, and then spread into a sheet.
  • polyethylene glycol PEG400 Lion Co., Ltd.
  • Maleic anhydride Z Maleic anhydride with a molar ratio of maleic acid 14Z86 Z Maleic anhydride Z Maleic acid Copolymer (ISP, GANTREZ S-97, molecular weight 1.5 million) 20 parts by mass 80 parts by weight of polyethylene glycol (PEG400 Lion Co., Ltd.) was kneaded at 90 ° C for 90 minutes, and then spread into a sheet.
  • ISP maleic acid 14Z86 Z Maleic anhydride Z Maleic acid Copolymer
  • Methyl beryl ether Z Maleic anhydride Copolymer (ISP, GAN TREZ AN-169) 100 mass%, 40 mass% water added, 90 ° C [Koo!
  • a copolymer of maleic anhydride and maleic anhydride having a molar ratio of maleic acid and maleic acid of 11Z89,
  • Hydroxypropylcellulose (HPC-H, Nippon Soda Co., Ltd.) 10 parts by mass and polyethylene glycol (PEG400, Lion Co., Ltd.) 90 parts by mass were kneaded at 90 ° C for 90 minutes, then in sheet form Spread out.
  • Table 1 shows the evaluation results of Examples 1A to 14A and Comparative Examples 1A to 4A.
  • Examples 1A to 14A were gel compositions having high tackiness and excellent gel-forming ability.
  • the prepared patch was cut into 10 cm ⁇ 14 cm to evaluate skin irritation.
  • the evaluation method was repeated on the inside of the forearm of five healthy panelists, and after 7 hours, and after 1 hour, the skin condition after 1 hour had passed. Observed.
  • the score was 3 points: no change from before application, 2 points: a little reddish, 1 point: very reddish, and the average score of each panel was calculated.
  • the average score is 2.5 points or more, there is no pain, the gel composition has low skin irritation, and no decrease in adhesiveness is observed after 7 hours of application. It was.
  • Comparative Examples 1A to 4A are expensive! Inability to achieve both cohesion and excellent gel-forming ability o
  • composition was kneaded at 90 ° C for 90 minutes, and then spread into a sheet.
  • Example 15A the patch had little skin irritation, high adhesiveness, and excellent gel-forming ability.
  • composition was kneaded at 90 ° C for 90 minutes, and then spread into a sheet.
  • Example 16A the patch had little skin irritation, high adhesiveness, and excellent gel-forming ability.
  • Example 1B- L0B
  • a transdermal absorption enhancer was mixed, and a binder was dispersed and mixed to obtain a gel composition.
  • the external preparation composition was applied onto the support so that the coating amount on the polyurethane film Z-knit laminated support was 0.7 (g / 70 cm 2 ). After heat treatment, the patch was cut into a size of 7 cm x 10 cm in length x width.
  • Example 1B ⁇ The components used in LOB are as follows.
  • Methyl vinyl ether Z Maleic anhydride Copolymer (ISP, GAN TREZ AN—139) 100 mass%, 8 mass% of water added, 90 ° C [Koo!
  • A As a polymer, a copolymer (weight average molecular weight 1,080,000) composed of methyl vinyl ether Z maleic anhydride Z maleic acid having a molar ratio of maleic anhydride Z maleic acid of 56Z44 was obtained. Obtained.
  • PEG300 Polyethylene glycol (weight average molecular weight 300, manufactured by Lion Corp.)
  • PEG400 Polyethylene glycol (weight average molecular weight 400, manufactured by Lion Corp.)
  • PG Propylene glycol (trade name "Propylene glycol PGjp", Arma Co., Ltd.
  • EG Ethylene glycol (trade name "Ethylene glycol (reagent)", Wako Pure Chemical Industries, Ltd.)
  • Hydroxypropylcellulose weight average molecular weight 1 million, trade name “HPC—H”, manufactured by Nippon Soda Co., Ltd.
  • Jetyl sebacate trade name “DES—SP”, manufactured by Nikko Chemicals Co., Ltd.
  • Diisopropyl adipate trade name “DID”, manufactured by Nikko Chemicals Co., Ltd.
  • Isopropyl myristate trade name “IPM—EX”, manufactured by Nikko Chemicals Co., Ltd.
  • Ololeic acid trade name “KOKOO”, manufactured by Higher Alcohol Industry Co., Ltd.
  • Example 1B Gel composition obtained from L0B Or use the patch and follow the method below
  • a patch (Example 1B etc.) was laminated on the worn skin, and a sample in the cell was taken every unit time.
  • the collected samples were subjected to high performance liquid chromatography analysis, and the amount of each medicinal component that permeated through the skin after 2 hours (medicinal component skin permeation amount, ⁇ g / cm 2 ) was determined.
  • a large amount of medicinal component skin permeation after 2 hours means that the initial percutaneous absorption is excellent.
  • Example 1B The adhesiveness of the patch prepared with L0B was evaluated based on the ball tack value when measured at an inclination angle of 30 ° according to the JIS Z-0237 test.
  • Seno ⁇ Jetinore cinnamate 10 10 10 Diisopropinole adipate 10

Abstract

L’invention concerne une composition de gel contenant un polymère (A) ayant une unité de répétition composée d’au moins une portion insaturée et une portion d’anhydride d’acide et une autre unité de répétition composée d’au moins une portion insaturée et une portion de composé d’acide correspondant à la portion d’anhydride d’acide, et un alcool polyhydrique (B). Le polymère (A) contient la portion d’anhydride d’acide et la portion de composé d’acide correspondant à la portion d’anhydride d’acide dans un rapport molaire de 15/85 à 85/15. Cette composition de gel présente une forte adhérence à la peau ou une muqueuse, avec une excellente capacité de formation de gel.
PCT/JP2006/303391 2005-02-24 2006-02-24 Composition de gel et procédé de fabrication idoine WO2006090824A1 (fr)

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Cited By (2)

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JP2015502940A (ja) * 2011-11-30 2015-01-29 アシノ アーゲー フェンタニルまたはその類似体の投与のための経皮治療システム
JP2015051961A (ja) * 2013-06-05 2015-03-19 国立大学法人九州大学 経皮吸収基材

Families Citing this family (2)

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JP5836561B2 (ja) * 2008-09-30 2015-12-24 小林製薬株式会社 皮膚外用剤
CN115970043A (zh) * 2022-09-09 2023-04-18 吉林大学 一种用于修复组织的黏合剂及其制备方法和应用

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JPS6392683A (ja) * 1986-10-08 1988-04-23 Advance Co Ltd 導電性粘着ゲル
JPH06212045A (ja) * 1992-08-13 1994-08-02 Adcock Ingram Pharmaceut Ltd ハイドロゲル組成物およびその製造法
JPH07503974A (ja) * 1992-02-25 1995-04-27 アラーガン、インコーポレイテッド ｐＨ感受性の可逆的にゲル化する浸蝕性ドラッグデリバリーシステム
JPH09169640A (ja) * 1995-10-18 1997-06-30 Sekisui Chem Co Ltd 皮膚疾患治療用外用剤
JP2003113077A (ja) * 2001-09-28 2003-04-18 Lion Corp 貼付剤
JP2003212760A (ja) * 2002-01-17 2003-07-30 Lion Corp ゲル組成物、ゲルシート
EP1506771A1 (fr) * 2003-08-04 2005-02-16 GC Corporation Gel à blanchissement pour les dents

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JPS6392683A (ja) * 1986-10-08 1988-04-23 Advance Co Ltd 導電性粘着ゲル
JPH07503974A (ja) * 1992-02-25 1995-04-27 アラーガン、インコーポレイテッド ｐＨ感受性の可逆的にゲル化する浸蝕性ドラッグデリバリーシステム
JPH06212045A (ja) * 1992-08-13 1994-08-02 Adcock Ingram Pharmaceut Ltd ハイドロゲル組成物およびその製造法
JPH09169640A (ja) * 1995-10-18 1997-06-30 Sekisui Chem Co Ltd 皮膚疾患治療用外用剤
JP2003113077A (ja) * 2001-09-28 2003-04-18 Lion Corp 貼付剤
JP2003212760A (ja) * 2002-01-17 2003-07-30 Lion Corp ゲル組成物、ゲルシート
EP1506771A1 (fr) * 2003-08-04 2005-02-16 GC Corporation Gel à blanchissement pour les dents

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2015502940A (ja) * 2011-11-30 2015-01-29 アシノ アーゲー フェンタニルまたはその類似体の投与のための経皮治療システム
JP2015051961A (ja) * 2013-06-05 2015-03-19 国立大学法人九州大学 経皮吸収基材

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