US20110028880A1 - Patch - Google Patents

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Publication number
US20110028880A1
US20110028880A1 US12/919,739 US91973909A US2011028880A1 US 20110028880 A1 US20110028880 A1 US 20110028880A1 US 91973909 A US91973909 A US 91973909A US 2011028880 A1 US2011028880 A1 US 2011028880A1
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United States
Prior art keywords
drug
salt
patch
metal salt
sensitive adhesive
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Abandoned
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US12/919,739
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English (en)
Inventor
Naoyuki Uchida
Naoko Fujita
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Hisamitsu Pharmaceutical Co Inc
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Hisamitsu Pharmaceutical Co Inc
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Application filed by Hisamitsu Pharmaceutical Co Inc filed Critical Hisamitsu Pharmaceutical Co Inc
Assigned to HISAMITSU PHARMACEUTICAL CO., INC. reassignment HISAMITSU PHARMACEUTICAL CO., INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: FUJITA, NAOKO, UCHIDA, NAOYUKI
Publication of US20110028880A1 publication Critical patent/US20110028880A1/en
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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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
    • 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
    • A61K9/7061—Polyacrylates

Definitions

  • the present invention relates to a patch.
  • a wide variety of drug-containing patches are developed in the expectations of reducing adverse reaction due to the avoidance of gastrointestinal tissue absorption of the drug and first-time passage to the liver and the improvement of patient compliance.
  • the drugs are distributed in the form of acid addition salt in the market from viewpoints of the handleability and stability thereof.
  • a drug acid addition salt is directly applied to the transdermal administration, or the like, it is generally known that the tissue absorption tends to be decreased.
  • the free base (free form) of a drug is preferable in view of the tissue absorption.
  • Patent Document 1 Japanese Unexamined Patent Application Publication No. 2007-16020
  • Patent Document 2 Japanese Unexamined Patent Application Publication No. 2002-509874
  • the present inventors found that when an easier production process wherein the free form of a drug and a metal salt (sodium chloride, or the like) are formed by the neutralization reaction of an acid addition salt of the drug and the metal salt is mixed with a pressure-sensitive adhesive base without being removed by filtration is employed, the metal salt formed by the neutralization reaction sometimes precipitates in the form of crystal, which aggregates and grows over time adversely affecting the production efficiency, product stability and product properties of a patch.
  • a metal salt sodium chloride, or the like
  • an object of the present invention is to provide a patch with suppressed over-time aggregation and growth of the metal salt formed when a drug salt is neutralized.
  • the present inventors conducted extensive studies to accomplish the above object and found that a salt derived from a drug acid addition salt formed after a neutralization reaction has a possibility to aggregate and grow around a small amount of the residue of a polar solvent (water, methanol, ethanol, or the like) used when a patch is produced or the neutralization reaction is carried out, and further found that the aggregation and growth can be suppressed by containing an adsorbent in a pressure-sensitive adhesive layer.
  • a polar solvent water, methanol, ethanol, or the like
  • the present invention is to provide a patch comprising a drug, a metal salt, an adsorbent and an pressure-sensitive adhesive base
  • the metal salt contains a substance capable of forming a drug salt by bonding to the drug or a component thereof, the content of the metal salt is the same or less number of moles of the substance capable of forming a drug salt by bonding to the drug or a component thereof when a drug salt is formed
  • the adsorbent is an adsorbent that adsorbs a polar solvent comprised in the patch.
  • the metal salt contained in the patch of the present invention is now described.
  • a basic drug as “A”
  • HX a substance capable of forming a drug acid addition salt by bonding to the drug “A” as “HX”
  • a drug acid addition salt as “A.HX”
  • the neutralization reaction mentioned above can be expressed as A.HX+MOH ⁇ A+MX+H 2 O and the salt formed as a result of the neutralization reaction is expressed as “MX”.
  • the metal salt in the patch of the present invention is the “MX” in this example and contains the component “X” of the substance “HX” capable of forming a drug salt by bonding to the drug “A”. Further, the content of the “MX” is not greater than the number of moles of the “HX” in the “A.HX”.
  • the adsorbent contained in the patch of the present invention is the one which adsorbs polar solvent such as the water produced by the above neutralization reaction and remaining in the patch, the water used in the production process and remaining in the patch, methanol and ethanol and consists of an inorganic and/or organic substance.
  • the metal salt contained in the patch of the present invention may be those formed during the production as described above, but may also be those formed in the patch after the production (i.e., during storage after the production and before use).
  • the drug is preferably a basic drug
  • the metal salt is preferably at least one selected from the group consisting of metal chlorides, metal bromides, metal iodides and organic acid metal salts.
  • a particularly preferable metal salt is at least one selected from the group consisting of sodium chloride, calcium chloride, aluminum chloride, stannous chloride, ferric chloride, magnesium chloride, potassium chloride, sodium citrate, sodium oxalate, sodium tartrate, sodium bromide and sodium succinate.
  • a preferable adsorbent is at least one adsorbent selected from the group consisting of talc, kaoline, bentonite, hydrous silica, fumed silica, polyvinylpyrrolidone, propylene glycol, amino alkyl methacrylate copolymers, crospovidone, carboxy vinyl polymers, lactic acid, acetic acid, zinc oxide; dextrin and dried aluminum hydroxide gel, owing to a high adsorbability of a polar solvent contained in the patch.
  • the basic drug be the one generated from a basic drug acid addition salt and that the basic drug acid addition salt be hydrochloride, acetate, sulfate, maleate, oxalate, citrate, hydroiodide, mesylate, tartrate or succinate of a basic drug.
  • the patch of the present invention may be applied directly to the skin as a so-called plaster, or may be applied as a plaster agent by forming an pressure-sensitive adhesive layer on a backing layer and containing the patch in the pressure-sensitive adhesive layer.
  • a patch in which the over-time aggregation and growth of a metal salt formed even when a drug salt is neutralized are suppressed is provided.
  • FIG. 1 is a perspective view showing a preferable embodiment of a patch of the present invention.
  • FIG. 1 is a perspective view showing a preferable embodiment of the patch of the present invention.
  • a patch 1 is provided with a backing layer 2 , a pressure-sensitive adhesive layer 3 laminated on the backing layer 2 , and a release sheet 4 attached on the pressure-sensitive adhesive layer 3 .
  • the pressure-sensitive adhesive layer 3 contains a drug, a metal salt and an adsorbent.
  • the metal salt contains a substance capable of forming a drug salt by bonding to the drug or a component thereof, and the content of the metal salt is not greater than the number of moles of the substance capable of forming a drug salt by bonding to the drug or a component thereof when a drug salt is formed in the same mole as the drug contained in the patch.
  • the pressure-sensitive adhesive layer 3 may be laminated to two or more layers, and may be laminated not only on one side but also on both sides of the backing layer 2 .
  • the release sheet 4 is removed before use.
  • the material for the backing layer 2 is not limited insofar, as it is typically usable for patches, and elastic or non-elastic materials can be used.
  • Specific examples of the preferably used material include films or sheets formed with a synthetic resin such as polyethylene terephthalate, polyethylene, polypropylene, polybutadiene, ethylene vinyl acetate polymer, polyvinyl chloride, polyester, nylon, and polyurethane, or laminates thereof, porous membranes, foams, fabrics and nonwoven fabrics and paper materials.
  • the pressure-sensitive adhesive layer 3 contains a pressure-sensitive adhesive base.
  • the pressure-sensitive adhesive base is not limited insofar as it can be a base for the pressure-sensitive adhesive layer 3 , and examples include acrylic pressure-sensitive adhesive bases, rubber pressure-sensitive adhesive bases, and silicone pressure-sensitive adhesive bases.
  • Examples of the preferably usable acrylic pressure-sensitive adhesive base include homopolymer or copolymer of (meth)acrylate, and copolymer of alkyl (meth)acrylate ester and other functional monomers.
  • (Meth)acryl means acryl or methacryl.
  • Examples of the preferably used rubber pressure-sensitive adhesive base include natural rubbers, synthetic rubbers, styrene-isoprene-styrene block copolymer (hereinafter abbreviated as “SIS”), isoprene rubber, polyisobutylene (hereinafter abbreviated as “PIB”), styrene-butadiene-styrene block copolymer (hereinafter abbreviated as “SBS”), styrene-butadiene rubber (hereinafter abbreviated as “SBR”) and polybutene, and the rubber pressure-sensitive adhesive base is typically used by adding a tackifier.
  • SIS styrene-isoprene-styrene block copolymer
  • PIB polyisobutylene
  • SBS styrene-butadiene-styrene block copolymer
  • SBR styrene-butadiene rubber
  • Usable silicone pressure-sensitive adhesive base are those containing polydimethyl siloxane or the like as a main component, and these are typically used by adding a tackifier such as MQ resin.
  • an acrylic ester copolymer or SIS to which a tackifier is added is particularly preferably used.
  • pressure-sensitive adhesive bases may be used singly, or two or more may be used in combination.
  • the amount of a pressure-sensitive adhesive base to be added is preferably 10 to 95% by mass, more preferably 15 to 80% by mass, particularly preferably 20 to 70% by mass, on the basis of the total mass of the pressure-sensitive adhesive layer 3 when considering the formation of the pressure-sensitive adhesive layer 3 and the tissue permeability of the active ingredients.
  • the pressure-sensitive adhesive layer 3 contains a drug.
  • the drug includes a drug salt which has become a free form by a neutralization reaction and a drug salt remained in the form of salt due to an incomplete neutralization.
  • the drug used for the production of the patch 1 is not limited, and examples include hypnotic/sedative agents (flurazepam hydrochloride, rilmazafone hydrochloride, phenobarbital, amobarbital, medetomidine hydrochloride, dexmedetosine hydrochloride, etc.), antipyretic/anti-inflammatory/analgesic agents (butorphanol tartrate, perisoxal citrate, acetaminophen, mefenamic acid, diclofenac sodium, aspirin, alclofenac, ketoprofen, flurbiprofen, naproxen, piroxicam, pentazocine, indomethacin, glycol salicylate, aminopyrine, loxoprofen, meloxicam, lomoxicam, etc.), steroidal anti-inflammatory agents (hydrcortisone, prednisolone, dexamethasone, betamethasone, etc.), stimulant (methamp
  • the drug can be used in combination of two or more as necessary if no inconvenience is caused by the interaction. Further, considering that the sufficient potency as a patch is attained, the product properties and tissue absorption, the drug is added in a proportion of preferably 0.5 to 50% by mass, particularly preferably 1 to 30% by mass, on the basis of the total mass of the pressure-sensitive adhesive layer 3 .
  • the drug is preferably a basic drug and more preferably a basic drug generated from an acid addition salt.
  • the acid addition salt form include hydrochloride, acetate, sulfate, maleate, oxalate, citrate, hydroiodide, hydrobromate, mesylate, tartrate, and succinate.
  • the pressure-sensitive adhesive layer 3 contains a metal salt containing a substance capable of forming a drug salt by bonding to the drug or a component thereof.
  • a metal salt is preferably those formed during production steps.
  • the drug is preferably a basic drug generated from an acid addition salt, it is desirable to use an acid addition salt of a basic drug as a starting material, cause a neutralization reaction of the drug by mixing the salt with a neutralizer, allow the free form of the drug having a higher tissue absorption to be present in the pressure-sensitive adhesive layer 3 and cause the metal salt produced as a result of the neutralization reaction of the drug to be also contained therein.
  • the type of the metal salt produced as a result of the neutralization reaction is determined by a drug salt and a neutralizer for neutralizing the drug salt.
  • the metal salt produced when neutralizing an acid addition salt of a basic drug is preferably any of metal chloride, metal bromide, metal iodide or organic acid metal chloride, and particularly preferably at least one of sodium chloride, calcium chloride, aluminum chloride, stannous chloride, ferric chloride, magnesium chloride, potassium chloride, sodium citrate, sodium oxalate, sodium tartrate, sodium bromide and sodium succinate.
  • the neutralizer used for the neutralization reaction is not limited, but when a basic drug produced from an acid addition salt is used, a strong base is suitable for completely desalting an acid addition salt of a basic drag, with a hydroxide of an alkali metal is particularly preferably used.
  • Specific examples of the neutralizer include sodium hydroxide, potassium hydroxide, and magnesium hydroxide, with sodium hydroxide being particularly preferable among these.
  • the neutralizer is added to convert a basic drug as a whole or a part to the state of free base (free form). To obviate the decomposition of the drug caused by an excessive amount of a neutralizer at this step, the neutralizer is preferably added within a range from 0.5 to 4 equivalent amounts to the equivalent amount of the drug acid base. The addition may be carried out once during the production steps, or carried out several times in a divided manner.
  • the patch 1 produced via a neutralization reaction contains a metal salt formed as a result of the neutralization in the pressure-sensitive adhesive layer 3 .
  • the metal salt present in the pressure-sensitive adhesive layer 3 is likely to aggregate and grow around a small amount of the residue of a polar solvent (water, methanol, ethanol, etc.) used during the production of the patch and the neutralization reaction, but the aggregation and growth of the metal salt can be suppressed by allowing the pressure-sensitive adhesive layer 3 to contain an adsorbent. Further, the crystal can be dispersed uniformly by containing an adsorbent. Owing to this, the production efficiency, product stability and product properties of the patch 1 are enhanced.
  • a polar solvent water, methanol, ethanol, etc.
  • the pressure-sensitive adhesive layer 3 contains an adsorbent
  • the applicable adsorbent include the inorganic substances and organic substances described as having hygroscopic properties, dampproofing properties, adsorptive properties among the additives listed in “Japanese Pharmaceutical Excipients Directory 2000, published on Apr. 28, 2000, 1st edition” and aminoalkyl methacrylate copolymers and zinc oxide, which are not described in the above “Japanese Pharmaceutical Excipients Directory 2000” but have been known to have adsorptive properties.
  • preferable examples include minerals such as talc, kaoline, and bentonite; silicone compounds such as fumed silica (Aerosil (registered trademark), etc.) and hydrous silica; metal compounds such as zinc oxide and dried aluminum hydroxide gel; weak acids such as lactic acid and acetic acid, sugars such as dextrin, and high molecular weight polymers such as polyvinylpyrrolidone, propylene glycol, aminoalkyl methacrylate copolymers, crospovidone, and carboxy vinyl polymers. These adsorbents may be used in combination of two or more as necessary.
  • the content of the adsorbent in the pressure-sensitive adhesive layer 3 is preferably 0.5 to 50% by mass on the total mass basis of the pressure-sensitive adhesive layer 3 .
  • a content of 0.5% by mass or lower tends not to achieve sufficient effects to control the aggregation and growth of the metal salt crystal or to disperse the crystal uniformly.
  • a content of 50% by mass or higher has a tendency of reducing the adhesion of the pressure-sensitive adhesive layer 3 , likely making it difficult to apply the patch.
  • the patch 1 of the present invention may contain as necessary, in addition to the above compositions, tackifier, plasticizer, absorption enhancer, antioxidant, filler, crosslinking agent, preservative and ultraviolet absorber.
  • Examples of the usable tackifier include rosin resins such as “Ester Gum (tradename, Arakawa Chemical Industries, Ltd.)”, “Hariester (tradename, Harima Chemicals, Inc.)”, “Pentalyn (tradename, Eastman Chemical Company)”, “Foral (tradename, Eastman Chemical Company)”, terpene resins such as “YS resin (tradename, Yasuhara Chemical Co., Ltd.)”, “Piccolyte (tradename, Loos and Dilworth)”, petroleum resins such as “Arkon (tradename, Arakawa Chemical Industries, Ltd.)”, “Regalrez (tradename, Eastman Chemical Company)”, “Piccolastic (tradename, Eastman Chemical Company)”, “Escorez (tradename, ExxonMobil Chemical Company)”, “Wingtack (tradename, Goodyear)”, “Quinton (tradename, Zeon Corporation)”, phenol resins, and xylene resins.
  • rosin resins such as “Ester Gum
  • tackifiers may be used singly or in combination of two or more.
  • the amount of the tackifier to be added is preferably 10 to 90% by mass, more preferably 15 to 70% by mass, particularly preferably 20 to 60% by mass, on the basis of the total mass of the pressure-sensitive adhesive layer 3 , when considering the sufficient adhesion of and the local irritation when removing the patch 1 .
  • plasticizer examples include petroleum oils such as paraffin process oils, naphthene process oils, and aromatic process oils; squalane, squalene; plant oils such as olive oil, camellia oil, castor oil, tall oil, and peanut oil; dibasic esters such as dibutyl phthalate, and dioctyl phthalate; liquid rubbers such as polybutene and liquid isoprene rubber; and diethylene glycol, polyethylene glycol, propylene glycol, and dipropylene glycol. These plasticizers can be used singly or two Or more can be used in combination.
  • liquid paraffin and liquid polybutene are preferably used.
  • the content of the above plasticizer in the pressure-sensitive adhesive layer 3 is preferably 1 to 60% by mass, more preferably 2 to 50% by mass, particularly preferably 3 to 40% by mass, on the basis of the total mass of the pressure-sensitive adhesive layer 3 , considering the maintenance of the sufficient adhesion of the patch 1 .
  • the preferably used absorption enhancer examples include fatty alcohols such as isostearyl alcohol, fatty acids such as capric acid, fatty acid derivatives such as propyleneglycol monolaurate and isopropyl myristate, propylene glycol, polyethylene glycol, and lauric acid diethanolamine. These absorption enhancers may be used singly, or in combination of two or more.
  • the content of the absorption enhancer is preferably 1 to 30% by mass, more preferably 3 to 20% by mass, particularly preferably 5 to 15% by mass, on the basis of the total mass of the patch 1 , considering the sufficient permeability of the active ingredients to the tissue, the local irritation, and the like, as a patch.
  • antioxidants examples include tocopherols and ester derivatives thereof, ascorbic acid, ascorbyl stearate, nordihydroguaiaretic acid, dibutylhydroxytoluene (hereinafter abbreviated as BHT), and butylated hydroxyanisole, with BHT being particularly preferably used.
  • filler examples include aluminum hydroxide, calcium carbonate, magnesium carbonate; silicates such as aluminum silicate and magnesium silicate; silicic acid, barium sulfate, calcium sulfate, calcium zincate, zinc oxide, titanium oxide, and the like.
  • crosslinking agent examples include thermosetting resins such as amino resin, phenol resin, epoxy resin, alkyd resin, and unsaturated polyester, isocyanate compounds, blocked isocyanate compounds, organic crosslinking agents as well as inorganic crosslinking agents such as metals and metal compounds.
  • preservative examples include disodium edetate, tetrasodium edetate, ethyl parahydroxybenzoate, propyl parahydroxybenzoate, and butyl parahydroxybenzoate.
  • ultraviolet absorber examples include p-aminobenzoic acid derivatives, anthranilic acid derivatives, salicylic acid derivatives, coumarin derivatives, amino acid compounds, imidazoline derivatives, pyrimidine derivatives, and dioxane derivatives.
  • antioxidants can be added in a total amount of preferably 5% by mass or less, more preferably 3% by mass or less, particularly preferably 1% by mass or less, on the basis of the total mass of the pressure-sensitive adhesive layer 3 .
  • a mixture for forming a pressure-sensitive adhesive layer 3 is prepared.
  • the above mentioned pressure-sensitive adhesive base, an acid addition salt of a drug, neutralizer, adsorbent and other ingredients are dissolved or dispersed in a solvent of the pressure-sensitive adhesive base to obtain a mixture for forming the pressure-sensitive adhesive layer 3 .
  • Examples of the usable solvent for the pressure-sensitive adhesive base include toluene, hexane, ethyl acetate, cyclohexane, heptane, butyl acetate, ethanol, methanol, xylene, and isopropanol. These are selected as necessary in accordance with the ingredients to be dissolved or dispersed, and may be used singly or in combination of two or more.
  • the obtained mixture for forming the pressure-sensitive adhesive layer 3 is spread directly on a backing layer 2 to form the pressure-sensitive adhesive layer 3 , or the mixture is spread on a release-treated paper or film to form the pressure-sensitive adhesive layer 3 and the backing layer 2 is placed thereon, followed by the press-bonding transfer of the pressure-sensitive adhesive layer 3 to the backing layer 2 .
  • a release sheet 4 for protecting the pressure-sensitive adhesive layer 3 is adhered on the pressure-sensitive adhesive layer 3 to obtain the patch 1 .
  • the content of the ingredients other than the solvent was ropinirole hydrochloride 15 parts by mass, sodium hydroxide 4 parts by mass (2.0 times equivalent to ropinirole hydrochloride), Aerosil (registered trademark) 5 parts by mass, liquid paraffin 24.1 parts by mass, SIS 20.1 parts by mass, and the terpene resin (YS resin) 31.8 parts by mass.
  • Patches of Examples 2 to 8 were produced respectively in the same manner as in Example 1 except that aminoalkyl methacrylate copolymer, crospovidone, lactic acid, talc, dextrin, propylene glycol or polyvinylpyrrolidone was used in place of Aerosil (registered trademark) as an adsorbent in the same parts by mass (Table 1).
  • a patch of Comparative Example 1 was produced in the same manner as in Example 1 except that an adsorbent was not contained (Table 1).
  • the mixing ratio of ropinirole hydrochloride, sodium hydroxide, liquid paraffin, SIS and the terpene resin (YS resin) was the same as in Example 1.
  • Patches of Comparative Examples 2 to 21 were produced respectively in the same manner as in Example 1 except that isostearic acid, oleic acid, sorbitan monolaurate, sorbitan monooleate, isopropyl myristate, isopropyl palmitate, hexyl laurate, glycerol monooleate, triacetin, lauryl alcohol, myristyl alcohol, oleyl alcohol, polybutene, propylene glycol monolaurate, Tween 80 (registered trademark), lauric acid diethanolamide, isostearyl alcohol, octyldodecanol or benzyl alcohol was used in place of Aerosil (registered trademark) as an absorbent in the same parts by mass (Table 1).
  • the content of the ingredients other than the solvent was terbinafine hydrochloride 10 parts by mass, sodium hydroxide 2.4 parts by mass (2.0 times equivalent to terbinafine hydrochloride), Aerosil (registered trademark) 5 parts by mass, isopropyl myristate 10 parts by mass and acrylic pressure-sensitive adhesive base in the acrylic pressure-sensitive adhesive 72.6 parts by mass.
  • Patches of Examples 10 to 22 were produced respectively in the same manner as in Example 9 except that aminoalkyl methacrylate copolymer, crospovidone, zinc oxide, bentonite, kaoline, polyvinylpyrrolidone, talc, hydrous silica or dried aluminum hydroxide gel was used in place of Aerosil (registered trademark) as an adsorbent in the same parts by mass (Table 2).
  • a patch of Comparative Example 21 was produced in the same manner as in Example 9 except that an adsorbent was not contained (Table 2).
  • the mixing ratio of terbinafine hydrochloride, sodium hydroxide, Aerosil (registered trademark), isopropyl myristate and the acrylic pressure-sensitive adhesive base was the same as in Example 9.
  • an acrylic pressure-sensitive adhesive material (National Starch and Chemical Company, Duro-TAK87-2516, solid content: 41.5%) was added to and mixed with the mixture to obtain a pressure-sensitive adhesive solution.
  • the solution was spread on a release-treated film to dry and remove the solvent, thereby forming a pressure-sensitive adhesive layer.
  • a backing layer was placed thereon and the pressure-sensitive adhesive layer was subjected to press-bonding transfer to obtain a patch.
  • the content of the ingredients other than the solvent was varenicline tartrate 10 parts by mass, sodium hydroxide 2.2 parts by mass (2.0 times equivalent to terbinafine hydrochloride), crospovidone 3 parts by mass and acrylic pressure-sensitive adhesive base in the acrylic pressure-sensitive adhesive 84.8 parts by mass.
  • Patches of Examples 24 and 25 were produced respectively in the same manner as in Example 23 except that aminoalkyl methacrylate copolymer or polyvinylpyrrolidone was used in place of crospovidone as an adsorbent (Table 3).
  • a patch of Comparative Example 22 was produced in the same manner as in Example 23 except that an adsorbent was not contained (Table 3).
  • the mixing ratio of varenicline tartrate and sodium hydroxide was made same as in Example 23, with the acrylic pressure-sensitive adhesive base being 87.8 parts by mass.
  • Tables 1 to 3 show the adsorbents, content thereof and the evaluation results.
  • the patches wherein no aggregates were found are indicated as “a”, those wherein small aggregates of an average particle size of 100 to 250 ⁇ m were found but practically having no problem are indicated as “b”, and those wherein many large aggregates of an average particle size of exceeding 250 ⁇ m are indicated as “c”.
  • Example 9 Aerosil 5 a (registered trademark)
  • Example 10 Aminoacryl methacrylate 10 a copolymer
  • Example 11 Aminoacryl methacrylate 15 a copolymer
  • Example 12 Crospovidone 10 a
  • Example 13 Crospovidone 15 a
  • Example 14 Zinc oxide 3 a
  • Example 15 Zinc oxide 5 a
  • Example 16 Zinc oxide 7 a
  • Bentonite 5 b Example 18 Kaoline 5 b
  • Example 19 Polyvinylpyrrolidone 5 b
  • Example 20 Talc 5 b
  • Example 21 Hydrous silica 5 b
  • Example 22 Dried aluminum 5 b hydroxide gel Comparative Example 21 None 0 c
  • a patch in which the over-time aggregation and growth of a metal salt formed even when a drug salt is neutralized are suppressed is provided.

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  • Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dermatology (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
US12/919,739 2008-02-27 2009-02-09 Patch Abandoned US20110028880A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP2008046804 2008-02-27
JP2008-046804 2008-02-27
PCT/JP2009/052181 WO2009107479A1 (fr) 2008-02-27 2009-02-09 Patch

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US20110028880A1 true US20110028880A1 (en) 2011-02-03

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Family Applications (3)

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US12/919,739 Abandoned US20110028880A1 (en) 2008-02-27 2009-02-09 Patch
US12/919,715 Active US8871249B2 (en) 2008-02-27 2009-02-09 Medicated patch
US12/919,723 Active 2029-09-10 US8580281B2 (en) 2008-02-27 2009-02-09 Medicated patch

Family Applications After (2)

Application Number Title Priority Date Filing Date
US12/919,715 Active US8871249B2 (en) 2008-02-27 2009-02-09 Medicated patch
US12/919,723 Active 2029-09-10 US8580281B2 (en) 2008-02-27 2009-02-09 Medicated patch

Country Status (5)

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US (3) US20110028880A1 (fr)
EP (3) EP2255809B1 (fr)
JP (3) JP5537412B2 (fr)
ES (3) ES2778724T3 (fr)
WO (3) WO2009107477A1 (fr)

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110223237A1 (en) * 2010-03-12 2011-09-15 Nitto Denko Corporation Selegiline-containing adhesive preparation
US20120315318A1 (en) * 2010-02-24 2012-12-13 Hisamitsu Pharmaceutical Co., Inc. Transdermal preparation
US20120321690A1 (en) * 2010-02-24 2012-12-20 Hisamitsu Pharmaceutical Co., Inc. Adhesive patch
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US8871249B2 (en) 2014-10-28
ES2536206T3 (es) 2015-05-21
US20110008398A1 (en) 2011-01-13
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JPWO2009107479A1 (ja) 2011-06-30
EP2258355A1 (fr) 2010-12-08
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US8580281B2 (en) 2013-11-12
US20110002976A1 (en) 2011-01-06
WO2009107477A1 (fr) 2009-09-03
WO2009107476A1 (fr) 2009-09-03
EP2258369B1 (fr) 2015-04-08
WO2009107479A1 (fr) 2009-09-03
EP2258355B1 (fr) 2020-01-22
JP5537412B2 (ja) 2014-07-02
EP2255809B1 (fr) 2017-08-23
EP2255809A4 (fr) 2011-05-04
ES2648197T3 (es) 2017-12-29
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EP2255809A1 (fr) 2010-12-01
EP2258369A4 (fr) 2011-05-04

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