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WO2006121209A1 - Agent thérapeutique contre l'eczéma et la dermatite - Google Patents

Agent thérapeutique contre l'eczéma et la dermatite Download PDF

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Publication number
WO2006121209A1
WO2006121209A1 PCT/JP2006/309974 JP2006309974W WO2006121209A1 WO 2006121209 A1 WO2006121209 A1 WO 2006121209A1 JP 2006309974 W JP2006309974 W JP 2006309974W WO 2006121209 A1 WO2006121209 A1 WO 2006121209A1
Authority
WO
WIPO (PCT)
Prior art keywords
dermatitis
eczema
zinc
zinc hyaluronate
hyaluronate complex
Prior art date
Application number
PCT/JP2006/309974
Other languages
English (en)
Japanese (ja)
Inventor
Isao Serizawa
Hideki Goto
Hiroyuki Miyazaki
Original Assignee
Takata Seiyaku Co., Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Takata Seiyaku Co., Ltd. filed Critical Takata Seiyaku Co., Ltd.
Priority to JP2007528350A priority Critical patent/JPWO2006121209A1/ja
Publication of WO2006121209A1 publication Critical patent/WO2006121209A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K33/00—Medicinal preparations containing inorganic active ingredients
    • A61K33/24—Heavy metals; Compounds thereof
    • A61K33/30—Zinc; Compounds thereof
    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
    • A61K31/726—Glycosaminoglycans, i.e. mucopolysaccharides
    • A61K31/728—Hyaluronic acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/04—Antipruritics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/06—Antipsoriatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/10—Anti-acne agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents

Definitions

  • the present invention relates to a therapeutic agent for eczema / dermatitis group such as atopic dermatitis.
  • the eczema / dermatitis group is a common and extremely common disease that accounts for approximately 30% of patients with skin diseases. From the viewpoint of pathological conditions, exogenous eczema involving external factors (eg, primary irritation contact dermatitis) and endogenous eczema involving internal factors of each individual (eg, allergic contact dermatitis) In general, it is often treated as a group of eczema / dermatitis in general.
  • diseases included in the group of eczema / dermatitis include contact dermatitis, a Topy dermatitis, seborrheic dermatitis, progressive sebaceous keratoderma, coin-like eczema, stasis dermatitis, chronic simple lichen, self-sensitizing dermatitis, sebum-deficient eczema, etc. . .
  • atopic dermatitis In the eczema / dermatitis group, atopic dermatitis, especially in infants, causes erythema and serous papules on the vagina, spreading over the entire face, moistening and ligating, and the affected area gradually becomes bent from infants to adults. It moves to the side and the skin becomes dry and thickened and not moistened. In either case, it is often accompanied by severe hemorrhoids, and scars and blood clots are often observed. Most cases occur during infancy, but it takes years or decades to treat. Nearly 10% of them remain as adult-type refractory atopic dermatitis that does not improve after 21 years of age.
  • Therapeutic agents such as steroids, antihistamines, and antiallergic agents are also used in atopic dermatitis, but it is difficult to cure this dermatitis by any treatment method or therapeutic agent. And, especially in the case of infants, administration of internal medicine such as tablets is not preferable in terms of dosage adjustment and side effects. Under such circumstances, it has been desired to develop a preparation for external use having an excellent healing promoting effect on the eczema / dermatitis group including the atopic dermatitis.
  • eczema / dermatitis group including contact dermatitis, atopic dermatitis, etc.
  • use of external preparations such as topical steroids and non-sterolide anti-inflammatory agents, antiallergic agents, antihistamines, linolenic acid, Including herbal medicine, steroids, cyclosborin, etc., specific desensitization therapy, non-specific desensitization therapy, bacterial vaccine therapy, drug bath therapy, PUVA therapy (a type of photochemical therapy), skin care, isolation
  • PUVA therapy a type of photochemical therapy
  • Steroid topical agents which are the main agents for the treatment of eczema and dermatitis groups, are divided into five stages according to the strength of action: we ak, me di uin, str ong, ve ry str ong, str on ge st, It is properly used depending on the severity.
  • oral antihistamines and antiallergic agents are used in combination, and in mild cases, moisturizers and non-sterile external preparations are used instead of sterol external preparations.
  • oral steroids are used.
  • evening chlorimus ointment an immunosuppressive agent, has been used against atopic dermatitis. Disclosure of the invention
  • oral medications such as tablets require time to onset of action and the dosage is adjusted depending on the degree of symptoms
  • it has been difficult to use for a long time because of the side effects such as general malaise and drowsiness.
  • topical antihistamines are often ineffective for itching such as atopic dermatitis and sebum-deficient eczema.
  • Steroid external preparations can dilate capillaries by long-term administration. Side effects such as associated erythema, skin atrophy, infectious disease induction and exacerbation were problems.
  • the present invention provides a therapeutic agent for eczema / dermatitis group comprising a zinc hyaluronate complex (aggregate).
  • the present invention also relates to the use of a zinc hyaluronate complex (aggregate) for the manufacture of a therapeutic agent for eczema and dermatitis.
  • the present invention further relates to a method for treating an eczema / dermatitis group therapeutic agent, comprising administering a zinc hyaluronate complex (aggregate) to a patient having eczema and dermatitis.
  • a zinc hyaluronate complex aggregate
  • topical steroids have been used to treat the eczema / dermatitis group, including contact dermatitis and atopic dermatitis, etc., but erythema with dilation of capillaries, skin atrophy, induction of infection, Has local side effects such as exacerbations.
  • oral antihistamines and allergic agents frequently used in combination with topical steroids have side effects such as general malaise and sleepiness. It provides treatment for the eczema / dermatitis group without these side effects.
  • the zinc hyaluronate complex (associate) of the present invention exhibits a higher effect than hyaluronic acid (sodium salt), zinc (chloride) and a simple mixture thereof, and exhibits a synergistic effect due to being a complex.
  • FIG. 1 is a graph showing the results of Example 1 showing the effects (skin symptom scores) of gel agents of various concentrations of the zinc hyaluronate complex (associate) of the present invention on an atopic dermatitis model. is there.
  • Figure 2 shows the results of Example 1 showing the effect (number of scratches) of gel agents of various concentrations of the zinc hyaluronate complex (associate) of the present invention on the atopic dermatitis model. It is a graph to represent. .
  • Figure 3 shows the results of comparing the effects (skin symptom scores) of the zinc hyaluronate complex of the present invention (aggregate) and the existing betamethanoic acid valerate preparation on an atopic dermatitis model.
  • Figure 4 shows the effect of the zinc hyaluronate complex (associate) of the present invention and the existing 0.12% betamethanoic acid benzoate preparation (number of scratches) on the atopic dermatitis model.
  • 6 is a graph showing the results obtained in Example 2, showing the comparison results.
  • Figure 5 compares the effects of the gel-free control, gel-based control, and various concentrations of the zinc hyaluronate complex (associate) of the present invention on allergic contact dermatitis. 6 is a graph showing the results obtained in Example 3.
  • FIG. 5 is a graph showing the results obtained in Example 4.
  • FIG. This result shows that the zinc hyaluronate complex (aggregate) of the present invention has a synergistic effect on the single use of sodium hyaluronate and zinc.
  • FIG. 6 is a graph showing the results obtained in Example 5.
  • Figure 8 compares the effects of gel-free controls, gel-based controls, and various concentrations of the zinc hyaluronate complex (associate) of the present invention on irritant contact dermatitis.
  • 10 is a graph showing the results of time-lapse observation obtained in Example 6.
  • Figure 9 is a graph showing the cumulative total for 7 days in Figure 8.
  • FIG. 10 shows a synergistic effect of the zinc hyaluronate complex (aggregate) of the present invention on irritant contact dermatitis, and is a draaf showing the results of time-lapse observation in Example 7.
  • Figure 11 is a graph showing the cumulative total for 7 days in Figure 10.
  • the eczema / dermatitis group which is the subject of the present invention, is an eczema lesion, that is, a skin disease whose main field is the epidermis. ), But there are exceptions.
  • punctate states such as papules and small blisters, erythema, papules, and various rash elements such as scabs, and wrinkles are considered as three signs.
  • skin symptoms become monotonous, and lichenification and infiltration become prominent.
  • the onset mechanism can be broadly divided into primary irritant and allergic mechanisms, but it is difficult to differentiate between clinical and histopathology.
  • Eczema ⁇ Dermatitis group is contact dermatitis, atopic dermatitis, seborrheic dermatitis, monetary eczema, autosensitizing dermatitis, stasis dermatitis, sebum-deficient eczema, sweat blister, V idal moss It is classified as scabies.
  • the treatment method except for the cause, is to apply an external preparation, mainly a topical external preparation, but it must be carefully selected. In the case of significant contact, it is necessary to use an antihistamine or an antiallergic agent (a chemical mediator release inhibitor).
  • atopic dermatitis atopic dermatitis, neural dermatitis, contact dermatitis, seborrheic dermatitis, self-sensitizing dermatitis, caterpillar dermatitis, sebum-deficient eczema, senile dermatitis, insect bite Photosensitivity, numbness, prurigo, blister, impetigo rash, eczema, ringworm, lichen, psoriasis, scabies, acne vulgaris, allergic dermatitis, infectious dermatitis, contact dermatitis, parasitic skin Targets include diseases, insect bites, eczema, rashes, mosquitoes, scratches, insect bites, rashes and athlete's foot caused by sweat and skin waste.
  • the active ingredient of the present invention is a zinc hyaluronate complex (associate)
  • Hyaluronic acid usually exists as a sodium salt and is a macromolecule described by Meyer et al., J. Biol. Chem. Vol. 107, p. 629 (1934).
  • Hyaluronic acid is a highly viscous darcosaminoglycan having alternating iS 1,3-glucuronic acid components and / 3 1,4-darcosamine components, and has a molecular weight of 50 kD to several million D.
  • Hyaluronic acid is found in connective tissue in all mammals and is present at high levels in the skin, vitreous body of the eye, synovial fluid, umbilical cord and cartilage tissue. Since hyaluronic acid is a fundamental component of connective tissue, it is biocompatible, biosorbable, and not immunogenic. For this reason, hyaluronic acid performs many biological functions such as lubrication and protection of articular cartilage.
  • the ratio of hyaluronic acid to zinc is a range in which these components exert a synergistic action as a therapeutic agent for the eczema / dermatitis group, and the weight ratio As the hyaluronic acid: zinc is in the range of about 5: 1 to 20: 1, preferably about 10: 1.
  • the average molecular weight of the zinc hyaluronate complex (aggregate) used in the present invention is preferably about 100 kD to 2, OOOkD, more preferably about 400 to 1,200 kD, for example, an average of about lOOOkD Molecular weight is preferred.
  • the zinc hyaluronate complex (aggregate) of the present invention can be produced, for example, by mixing an aqueous solution of sodium hyaluronate and a zinc salt such as an aqueous solution of zinc chloride (European Patent Specification). No. EP 0413016).
  • Zinc hyaluronate complex (aggregate) was not systemically toxic even when administered subcutaneously to rats and mice at a physical maximum dose of 200 mg Zkg.
  • the dosage form is, for example, a cream, paste, gel, emulsion, liquid, etc. by dissolving or mixing the zinc hyaluronate complex (compound) of the present invention or additives in the base.
  • Products formed into shapes, liniments, ointments, lotions, etc., in which the zinc hyaluronate complex (associate) or additive of the present invention is dissolved or mixed and dispersed in the base are spread on the support.
  • the zinc hyaluronate complex (aggregate) is preferably administered parenterally, particularly applied directly to the skin.
  • the effective dose of the zinc hyaluronate complex (aggregate) of the present invention is 0.01 to 1 mg, preferably 0.03 to 0.5 mg per person, depending on the symptoms. It can be administered one to several times a day.
  • Bases for producing zinc hyaluronate composites (associates) as external preparations should be applicable to ordinary liquids, plasters, ointments, creams, lotions, sprays, etc. That's fine.
  • An ointment can be produced by using a method for producing an ordinary ointment.
  • the active ingredient and the base can be heated and stirred, dispersed by heating, and then cooled to room temperature with stirring.
  • Creams can usually be produced by using a method for producing creams.
  • the base can be produced under heating and stirring, and the active ingredient itself or a solution containing it can be added under heating and stirring, and the resulting emulsion can be cooled to room temperature.
  • Lotions can usually be produced by using a method for producing a lotion, such as an oily base or a mixture of a heated and melted oily base and an aqueous base, the active ingredient itself or A solution containing this can be added under heating and stirring, then an aqueous base is added, and the resulting liquid can be cooled to room temperature.
  • a method for producing a lotion such as an oily base or a mixture of a heated and melted oily base and an aqueous base, the active ingredient itself or A solution containing this can be added under heating and stirring, then an aqueous base is added, and the resulting liquid can be cooled to room temperature.
  • Patches can usually be manufactured by using the method of manufacturing patches.
  • an additive is added to a mixed base of a heated and melted oily base and an aqueous base while stirring.
  • Active ingredient itself or containing it
  • the active ingredient itself by adding the solution to be heated under stirring and spreading the resulting plaster into a non-woven fabric and cutting it into an appropriate size, or by mixing it with a heated and melted oily base.
  • a solution containing this is added under heating and stirring, and then this is added to the heated and melted mixture of synthetic resin with stirring, and the resulting plaster is spread on a nonwoven fabric or woven fabric, It can be manufactured by cutting to an appropriate size.
  • Gels can usually be produced by using a method for producing a gel. For example, after a gel base is uniformly dissolved, an active ingredient is added, heated, dissolved, dispersed, etc. Any of the dosage forms can be produced by a normal manufacturing method.
  • the effective component is impermeable or hardly permeable and flexible, for example, cellulose acetate, ethyl cellulose, polyethylene, polypropylene, Polyvinyl chloride, vinyl acetate-vinyl chloride copolymer, ethylene monovinyl acetate copolymer, ethylene vinyl acetate-carbon monoxide copolymer, ethylene monobutyl acrylate-carbon monoxide copolymer, polyvinylidene chloride, polyurethan, Nylon, polyethylene terephthalate, polybutylene terephthalate, etc.
  • any known one can be used, for example, Lil pressure-sensitive adhesives, rubber adhesives, silicone-based adhesive, a urethane adhesive or the like can be mentioned, et al is an acrylic pressure-sensitive adhesives, rubber-based adhesive is preferably used. Further, when spreading on the above-mentioned support, any property such as solvent-based, emulsion-based, or hot-melt-based adhesive can be used.
  • inorganic fillers such as kaolin, bentonite and titanium oxide, viscosity modifiers, anti-aging agents, PH modifiers, humectants such as glycerin and propylene glycol, buffering agents, preservatives, fragrances, etc. May be added.
  • the therapeutic agent for eczema and dermatitis comprises 0.001% to 5%, preferably 0.01% to 2%, of the zinc hyaluronate complex (associate) of the present invention together with a conventional pharmaceutical carrier. Can be contained.
  • drugs can be blended and used in the composition according to the present invention.
  • the type of the drug is not particularly limited, and for example, a local anesthetic, a vasoconstrictor, an antihistamine, an astringent, a bactericidal agent, an anti-inflammatory enzyme, vitamins, a crude drug component, and the like can be blended.
  • Example 1 Action against atopic dermatitis.
  • NC mice male NC / Nga mice
  • the test was conducted using a complex of hyaluronic acid and zinc as a test substance.
  • the group treated with zinc hyaluronate complex (aggregate) was administered 0.1, 0.2, 0.5 and 1.0% gel preparations 3 times a day, 15 OmgZ times on the shaved neck of the animal. Repeated application for 10 days.
  • a placebo group (base) was applied in the same manner (15 animals in each group).
  • the efficacy of the zinc hyaluronate complex (aggregate) was evaluated by scoring the cervical dorsal symptom on a five-point basis, counting the number of scratches on the test substance application site, and histopathological examination. Evaluation was performed.
  • a topical corticosteroid (0.5% zinc hyaluronate complex (aggregate)) for the prevention of the progression of dermatitis
  • a test was conducted using a zinc hyaluronate complex (aggregate) as a test substance.
  • the 0.5% zinc hyaluronate complex (associate) gel group received 0.5% zinc hyaluronate complex (aggregate) gel daily on the shaved neck of the animal. It was applied 3 times and 1 50 mgZ times for 10 days.
  • valerate solid zonate group was applied to the shaved cervical dorsal area of the animal 0.12% of valerate solid zonate once a day on the 1st, 3rd, 5th, 7th, and 9th days. l O Omg / application.
  • the base group and the non-treated group were applied in the same manner as the zinc hyaluronate complex (aggregate) (15 per group).
  • the efficacy of the zinc hyaluronate complex was evaluated by scoring the cervical dorsal symptom on a 6-point basis, measuring the percentage by leukocyte type, measuring IgE, and histopathological examination. .
  • DNCB dinitrochlorobenzene
  • Hyaluron as a comparative reference for the effect on ear wing swelling
  • a test was conducted using 9-week-old male BALB / C mice. went.
  • Example 3 In the same manner as in Example 3, a DNCB solution was applied to mice to induce sensitization, and an ear wing swelling model was prepared.
  • Example 3 uncoated control, gel base control, 0.5% zinc hyaluronate complex (aggregate) gel, 0.488% sodium hyaluronate gel and 0.083% zinc chloride gel.
  • Example 5 Symptom-improving action of allergic contact dermatitis
  • Example 6 Symptom improvement effect of irritant contact dermatitis
  • a model was prepared by applying a patch test adhesive paste with 50 iL of 2% SLS aqueous solution dripped on the left and right backs of Std: HarUy guinea pigs for 12 hours. Each site was made of zinc hyaluronate.
  • the complex (aggregate) gel (0.25%, 0.5%, 0.75% and 1%) or gel base, 0.035 g each, was applied once a day for 6 days.
  • a non-application group was also provided as a control.
  • Macroscopic findings of skin symptoms were evaluated according to the Draize criteria, and a erythema score was obtained.
  • the results for 7 days are shown in Fig. 8, and the cumulative total for 7 days is shown in the graph in Fig. 9.
  • the gel base was applied after the 5th day. A significant decrease in erythema score was observed.
  • the cumulative period of 7 days a significantly lower score was obtained in the 1% zinc hyaluronate complex (aggregate) application group compared to the base.
  • Example 7 Synergistic effect of zinc hyaluronate complex (aggregate) in improving symptoms of irritant contact dermatitis
  • Example 6 The same experiment as in Example 6 was repeated. However, in order to confirm the synergistic effect, the concentration of zinc hyaluronate complex (aggregate) in the gel was fixed at 1%, and for comparison, 0.976% sodium hyaluronate gel (on 1% zinc hyaluronate) Corresponding hyaluronic acid), 0.166% zinc chloride gel (containing zinc equivalent to 1% zinc hyaluronate), sodium chloride-containing gel and mixed gel of sodium hyaluronate gel and zinc chloride gel (1 % Containing hyaluronic acid and zinc corresponding to zinc hyaluronate).
  • the zinc hyaluronate complex (aggregate) of the present invention has a low erythema score not only when compared with sodium hyaluronate gel and zinc chloride gel but also when compared with mixed gel. Cumulative effect was confirmed by bringing the total to the complex.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Dermatology (AREA)
  • Epidemiology (AREA)
  • Pulmonology (AREA)
  • Immunology (AREA)
  • Molecular Biology (AREA)
  • Inorganic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

La présente invention concerne un agent thérapeutique contre l'eczéma et la dermatite qui comprend un complexe (association) d’acide hyaluronique et de zinc au titre de principe actif. Ce complexe présente un effet synergique par rapport au cas de l'acide hyaluronique ou du zinc, constituants du complexe, employés seuls.
PCT/JP2006/309974 2005-05-13 2006-05-11 Agent thérapeutique contre l'eczéma et la dermatite WO2006121209A1 (fr)

Priority Applications (1)

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JP2007528350A JPWO2006121209A1 (ja) 2005-05-13 2006-05-11 湿疹・皮膚炎群治療剤

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JP2005-141366 2005-05-13
JP2005141366 2005-05-13

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010116388A (ja) * 2009-03-10 2010-05-27 Nr Laboratory:Kk 消化管溶性剤型

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH08208488A (ja) * 1994-12-05 1996-08-13 Denki Kagaku Kogyo Kk 皮膚外用剤
JP2571312B2 (ja) * 1989-02-24 1997-01-16 ケミカル ワークス オブ ゲデオン リヒター リミティド ヒアルロン酸会合物を含む新規組成物及びそれを調製するための方法
JP2001278791A (ja) * 2000-03-31 2001-10-10 Takada Seiyaku Kk 皮膚疾患処置用ゲル組成物
JP2003160464A (ja) * 2001-11-28 2003-06-03 Denki Kagaku Kogyo Kk ヒアルロン酸及び／又はその塩の水溶液の安定化組成物

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2571312B2 (ja) * 1989-02-24 1997-01-16 ケミカル ワークス オブ ゲデオン リヒター リミティド ヒアルロン酸会合物を含む新規組成物及びそれを調製するための方法
JPH08208488A (ja) * 1994-12-05 1996-08-13 Denki Kagaku Kogyo Kk 皮膚外用剤
JP2001278791A (ja) * 2000-03-31 2001-10-10 Takada Seiyaku Kk 皮膚疾患処置用ゲル組成物
JP2003160464A (ja) * 2001-11-28 2003-06-03 Denki Kagaku Kogyo Kk ヒアルロン酸及び／又はその塩の水溶液の安定化組成物

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* Cited by examiner, † Cited by third party
Title
DATABASE MEDLINE STN U.S. NATIONAL LIBRARY OF MEDICINE (NLM); 5 June 2006 (2006-06-05), ILLES J. ET AL.: "Zinc-hyaluronate: an original organotherapeutic compound of Gedeon Richter Ltd, Acta", XP003007119 *
PHARMACEUTICA HUNGARICA, vol. 72, no. 1, 2002, BETHESDA, MD, USA, pages 15 - 24 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010116388A (ja) * 2009-03-10 2010-05-27 Nr Laboratory:Kk 消化管溶性剤型

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