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WO2018066341A1 - Composition pour cavité buccale, et procédé d'inhibition de variation de couleur de préparation et de séparation de liquide associés - Google Patents

Composition pour cavité buccale, et procédé d'inhibition de variation de couleur de préparation et de séparation de liquide associés Download PDF

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Publication number
WO2018066341A1
WO2018066341A1 PCT/JP2017/033453 JP2017033453W WO2018066341A1 WO 2018066341 A1 WO2018066341 A1 WO 2018066341A1 JP 2017033453 W JP2017033453 W JP 2017033453W WO 2018066341 A1 WO2018066341 A1 WO 2018066341A1
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WO
WIPO (PCT)
Prior art keywords
composition
component
mass
liquid separation
oral cavity
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/JP2017/033453
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English (en)
Japanese (ja)
Inventor
祐輔 吉田
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Lion Corp
Original Assignee
Lion Corp
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Filing date
Publication date
Application filed by Lion Corp filed Critical Lion Corp
Publication of WO2018066341A1 publication Critical patent/WO2018066341A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/20—Halogens; Compounds thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/20—Halogens; Compounds thereof
    • A61K8/21—Fluorides; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/24—Phosphorous; Compounds thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35—Ketones, e.g. benzophenone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/67—Vitamins
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses

Definitions

  • the present invention relates to an oral composition containing hinokitiol and having excellent appearance stability over time, and a method for inhibiting formulation discoloration and liquid separation in the oral composition.
  • Hinokitiol is often used in oral compositions such as dentifrices as a natural product-derived ingredient that has antibacterial and bactericidal effects on periodontal disease-causing bacteria in the oral cavity, but it causes discoloration of the preparation and phase separation.
  • Patent Document 1 Japanese Patent No. 5600872 proposes that discoloration and phase-liquid separation of a hinokitiol-containing toothpaste composition can be suppressed by a specific combination of edetic acid, ethanol and water.
  • Patent Document 2 Japanese Patent Laid-Open No.
  • ascorbic acid phosphate ester such as magnesium ascorbate or a salt thereof is a medicinal component for oral compositions, but is also known as a component with problems such as discoloration of preparations.
  • JP-A-11-286422 and JP-A-2000-256152 have proposed oral compositions containing acid esters in which discoloration is suppressed.
  • the ascorbic acid derivative itself has a discoloration suppressing effect.
  • the present invention has been made in view of the above circumstances, and an object of the present invention is to provide an oral composition containing hinokitiol and having excellent appearance stability over time.
  • the present inventor has further added fluoride ions to the oral composition containing both hinokitiol and ascorbic acid phosphate ester or salts thereof, both of which have coloring problems. It was found that, when blended in a specific amount and proportion, coloring was suppressed, and the appearance of liquid separation by the combined use system was prevented, excellent appearance stability was given over time, and a good feeling of use could be imparted. . That is, in the present invention, it contains (A) hinokitiol, (B) ascorbic acid phosphate ester or salt thereof, and (C) fluorine ion, and the content of (C) component is 0.0001 to 0.27% by mass.
  • composition for oral cavity in which ((A) + (B)) / (C) indicating the blending ratio of the components (A) and (B) to the component (C) is 0.5 to 11,000 as a mass ratio
  • the product was found to have excellent appearance stability over time and good usability (astringency, bitterness, tastelessness) and led to the present invention.
  • the present inventor has combined the component (C) with the combination system of the components (A) and (B), and the content of the component (C) and (( The mass ratio of A) + (B)) / (C) was within a specific range, and the discoloration and liquid separation of the preparation were suppressed over time, and the taste was also improved.
  • the unique and exceptional problem that the problem of discoloration that cannot be achieved simply by blending the (A) component and the (C) component can be solved by using a three-component system including the (B) component having the same discoloration problem. It was possible to give a good effect.
  • the preparation is discolored without causing significant discoloration even after storage at 50 ° C. for 1 month.
  • An excellent discoloration suppressing effect that suppresses and an excellent liquid separation suppressing effect that sufficiently suppresses without causing significant liquid separation of 1 cm or more when extruded from a container accommodated even after storage at 50 ° C. for 1 month, and ( Astringent taste, bitter taste, and off-flavor produced by the combined use of components A) and (B) can be suppressed to give a good feeling of use.
  • the present invention [I] (A) Hinokitiol, (B) Ascorbic acid phosphate or a salt thereof, (C) Fluorine ions are contained, the content of component (C) is 0.0001 to 0.27% by mass, and the blending ratio of components (A) and (B) to component (C) is shown (( A composition for oral cavity, wherein A) + (B)) / (C) is a mass ratio of 0.5 to 11,000, and [II] (A) hinokitiol and (B) ascorbic acid phosphate An oral composition containing an ester or a salt thereof, (C) 0.0001 to 0.27% by mass of fluorine ions, and the blending ratio of the components (A) and (B) to the component (C) (( A preparation comprising the components (A) and (B) in the composition for oral cavity, wherein A) + (B)) / (C) is blended in a mass ratio of 0.5 to 11,000.
  • the present invention it is possible to provide a composition for oral cavity containing hinokitiol and ascorbic acid phosphate or a salt thereof, which has excellent appearance stability over time and good usability (astringency, bitterness, tastelessness). .
  • the oral composition of the present invention has a high preventive or ameliorating effect on periodontal diseases, and is useful for preventing or improving periodontal diseases.
  • composition for oral cavity of this invention contains (A) hinokitiol, (B) ascorbic acid phosphate ester or its salt, and (C) fluorine ion.
  • Hinokitiol is a unique component contained in Aomori Hiba, a natural tree, and is a crystalline acidic compound. Other tree species containing hinokitiol include Taiwan cypress, North American Western red cedar and the like. Hinokitiol has strong antibacterial activity and a broad antibacterial spectrum, is one of the few natural fungicides, and has an effect of preventing or improving periodontal diseases.
  • hinokitiol includes a chemically synthesized product, and in the present invention, a natural product or a synthetic product may be used. Such hinokitiol is widely used in foods, cosmetics, pharmaceuticals, agricultural supplies, building materials, baits, etc., and in the present invention, commercially available products used for these can be used. it can.
  • the amount of hinokitiol is preferably 0.005 to 0.5% (mass%, the same applies hereinafter) of the whole composition, more preferably 0.01 to 0.2%. As the blending amount increases, the effect of preventing or improving periodontal disease increases, but when it is 0.5% or less, the feeling of use (astringency, bitterness, and taste) can be maintained sufficiently and satisfactorily.
  • Ascorbic acid phosphates include those in which one or more of the hydroxyl groups at positions 2, 3, 5, and 6 of ascorbic acid are converted to phosphates, for example, ascorbic acid-2- Examples thereof include phosphoric acid ester, ascorbic acid-3-phosphate ester, ascorbic acid-6-phosphate ester and the like. Examples of these salts include sodium salt, potassium salt, calcium salt, magnesium salt and the like. 1 type (s) or 2 or more types chosen from these can be used as (B) ascorbic acid phosphate ester or its salt.
  • a derivative in which the hydroxyl group at the 2-position or 3-position of ascorbic acid is converted to a phosphate ester is preferable, and a magnesium salt or sodium salt of ascorbyl 2-phosphate ester is more preferable.
  • a magnesium salt is particularly preferred.
  • the blending amount of ascorbic acid phosphate or a salt thereof is preferably 0.1 to 5%, more preferably 0.2 to 4% of the entire composition. When it is 0.1% or more, the effect of suppressing discoloration and liquid separation of the present invention is particularly excellent. When it is 5% or less, the effect of suppressing discoloration and liquid separation is particularly good.
  • Fluorine ions can be blended as a fluorine-containing compound that supplies fluorine ions.
  • the fluorine-containing compound include sodium fluoride, sodium monofluorophosphate, tin fluoride and the like, and one or more selected from these can be used.
  • sodium fluoride and sodium monofluorophosphate are preferable from the viewpoint of imparting the effect of the present invention, and sodium monofluorophosphate is more preferable.
  • the blending amount of (C) fluorine ions is 0.0001 to 0.27%, preferably 0.001 to 0.19% of the entire composition.
  • the fluorine-containing compound is blended within the range of the blending amount of the fluorine ions, and the blending amount can be obtained by conversion from the fluorine ion amount.
  • the preferable blending amount is 0.001 to 2%, particularly 0.01 to 1.4% of the whole composition.
  • the preferred blending amount is 0.0003 to 0.58%, particularly 0.001 to 0.41% of the entire composition.
  • ((A) + (B)) / (C) indicating the ratio of the total blending amount of the components (A) and (B) to the blending amount of the fluorine ion of the component (C) is 0 as a mass ratio.
  • the discoloration-suppressing effect and liquid separation-suppressing effect of the preparation are excellent, and the feeling of use (astringency, bitterness, tastelessness) is excellent.
  • ((A) + (B)) / (C) is less than 0.5, the effect of suppressing liquid separation is reduced, and the feeling of use (astringency, bitterness, and taste) is inferior.
  • it exceeds 11,000 the discoloration suppressing effect and the liquid separation suppressing effect of the preparation are lowered, and the feeling of use (astringency, bitterness, tastelessness) is inferior.
  • the oral composition of the present invention is not limited in its shape and dosage form, but in particular, it is prepared in a semi-solid form such as paste or gel and used as a dentifrice such as toothpaste or gel toothpaste, especially toothpaste. Can be suitably prepared.
  • composition for oral cavity of the present invention in addition to the above-mentioned components, known oral additive components (pharmacologically acceptable carriers) according to the dosage form and the like within a range not impairing the effects of the present invention Can be blended.
  • an additive component in dentifrices, for example, abrasives, binders, surfactants, wetting agents, coloring agents, preservatives, sweeteners, fragrances, pH adjusters, (A), (B), (C) Examples include active ingredients other than the ingredients.
  • the specific example of an additional component is shown below, the component which can be mix
  • silica-based abrasives such as silica gel, precipitated silica, anhydrous silicic acid, aluminosilicate, zirconosilicate, calcium pyrophosphate, calcium carbonate, aluminum hydroxide, alumina, magnesium carbonate, tribasic magnesium phosphate, zeolite, Examples thereof include zirconium silicate, hydroxyapatite, and a synthetic resin abrasive.
  • the blending amount of the abrasive is usually 2 to 40%, particularly 10 to 25% of the whole composition.
  • a silica-based abrasive is preferred as the abrasive, particularly in terms of suppressing discoloration of the preparation, and a silica-based abrasive is particularly preferred as the main abrasive.
  • abrasives other than silica-based abrasives may not be blended, but when blended, the blending amount is 10% or less, particularly 1 to 8% is preferable, and not blended (0%) is more preferable.
  • gums such as sodium polyacrylate, xanthan gum, guar gum, carboxymethylcellulose sodium, hydroxyethylcellulose, hydroxypropylcellulose, hydroxypropylmethylcellulose, hydroxymethylethylcellulose, methylcellulose, cellulose derivatives such as cationized cellulose, carrageenan, Examples include sodium alginate, montmorillonite, and gelatin. Especially, the 1 type or 2 types chosen from a xanthan gum and a sodium polyacrylate from the point of the expression of the liquid-separation inhibitory effect is preferable.
  • the amount of the binder is usually 0.1 to 10%, particularly 0.5 to 5% of the whole composition.
  • an anionic surfactant such as sodium lauryl sulfate and sodium myristyl sulfate, sodium dodecylbenzene sulfonate, hydrogenated coconut fatty acid monoglyceride sodium monosulfate, sodium lauryl sulfoacetate, sodium ⁇ -olefin sulfonate, sodium lauroyl sarcosine , Acylamino acid salts such as lauroylmethyltaurine, ⁇ -sulfo fatty acid alkyl ester / sodium, alkyl phosphate ester cationic surfactant: distearylmethylammonium chloride, stearyldimethylbenzylammonium chloride
  • Nonionic surfactant sorbitan fatty acid
  • wetting agent examples include propylene glycol, pentylene glycol, hexylene glycol, octylene glycol, polyethylene glycol having an average molecular weight of 200 to 6,000 (average molecular weight described in Quasi-drug Raw Material Standard 2006), ethylene glycol, 1,3 -Polyhydric alcohols such as butylene glycol and glycerin, sugar alcohols such as sorbitol, xylitol, erythritol, and reduced starch saccharified product.
  • the amount of the wetting agent is usually 5 to 50%, particularly 20 to 45% of the whole composition.
  • sweetening agent examples include saccharin sodium, aspartame, stevioside, stevia extract, paramethoxycinnamic aldehyde, neohesperidyl dihydrochalcone, perilartin and the like.
  • fragrance those known as oral fragrances can be used.
  • menthol anethole, carvone, eugenol, limonene, n-decyl alcohol, citronellol, ⁇ -terpineol, citronellyl acetate, cineol, linalool, ethyl linalool, vanillin, thymol, spearmint oil, peppermint oil, lemon oil, orange oil
  • Examples include sage oil, rosemary oil, cinnamon oil, pimento oil, cinnamon oil, perilla oil, winter green oil, clove oil, eucalyptus oil and the like.
  • the blending amount of the fragrance is preferably 0.000001 to 2% of the entire composition.
  • the pH adjuster examples include organic acids such as citric acid, lactic acid, malic acid and salts thereof, and inorganic compounds such as hydrochloric acid, sodium hydroxide, potassium hydroxide, disodium hydrogen phosphate, sodium dihydrogen phosphate, and the like. .
  • the pH (25 ° C.) of the composition is preferably 8 or more, particularly 8.1 to 9.3, particularly from the viewpoint of the stability of the component (B).
  • water is used as a solvent.
  • the lower monohydric alcohol such as ethanol may be added in an amount of about 1 to 10%, but may not be added (0%).
  • the amount of water is not particularly limited, and can usually be in the range of 5 to 95% by mass.
  • the oral composition of the present invention when it is a dentifrice, it can be preferably 5 to 70%, more preferably 10 to 60%.
  • compositions (toothpaste) having the compositions shown in Tables 1 and 2 were prepared by a conventional method and evaluated by the following methods. The results are shown in the table.
  • ((A) + (B)) / (C) in the table is a mass ratio indicating the ratio of the total blending amount of the (A) and (B) components to the blending amount of the fluorine ions of the (C) component. Yes (the same applies below).
  • the pH (25 ° C.) of each composition was adjusted within the range of 8.1 to 9.3 (the same applies hereinafter).
  • the compositions for oral cavity of the Examples all have the effects of the (A) and (B) components effectively acting to sufficiently exhibit the medicinal effects, and have a high periodontal disease prevention or improvement effect.
  • Discoloration evaluation method Three oral compositions filled in an 8 mm diameter laminated tube were stored at 50 ° C. for 1 month or ⁇ 5 ° C. for 1 month, and then the oral composition on a straw half paper. The object was extruded 10 cm, and five expert panelists of the test subjects observed changes in color tone of the product stored at 50 ° C. compared to the product stored at ⁇ 5 ° C., and sensory evaluation was performed according to the following four grades. The average value of the score results of five people for three was obtained and judged according to the following evaluation criteria. ⁇ The above was deemed acceptable because discoloration of the preparation was suppressed over time.
  • Criterion criteria for liquid separation 4 points No liquid separation is observed 3 points: When extruded, there is almost no liquid separation at the mouth, and there is no problem in use 2 points: When pushed, liquid separation is 1 to 3 cm at the mouth Permitted 1 point: When extruded, liquid separation exceeds 3 cm at the mouth. Evaluation criteria ⁇ : 3.5 or more and 4.0 or less ⁇ : 3.0 or more and less than 3.5 ⁇ : 2 .0 point or more and less than 3.0 point ⁇ : less than 2.0 point
  • composition for oral cavity of Reference Example did not cause liquid separation over time, and did not develop astringency, bitterness or off-taste, and had a good feeling of use.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Inorganic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Emergency Medicine (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne une composition pour cavité buccale qui comprend (A) un hinokitiol, (B) un ester de phosphate d'acide ascorbique ou un sel de celui-ci et (C) des ions fluor. La teneur en composant (C) est comprise entre ０,０００１ et ０,２７, et （（Ａ）＋（Ｂ））／（Ｃ） indiquant la proportion dans laquelle les composants (A) et (B) sont mélangés au composant (C), est compris entre ０,５ et １１０００ en rapport massique. En outre, l'invention concerne un procédé d'inhibition de variation de couleur de préparation et de séparation de liquide à l'aide des composants (A) et (B) dans ladite composition pour cavité buccale. Selon ce procédé, le composant (C) est mélangé à la composition pour cavité buccale dans laquelle sont mélangés lesdits composants (A) et (B) selon ladite plage de quantité spécifique, et de sorte que （（Ａ）＋（Ｂ））／（Ｃ） se trouve à l'intérieur de ladite plage spécifique.
PCT/JP2017/033453 2016-10-06 2017-09-15 Composition pour cavité buccale, et procédé d'inhibition de variation de couleur de préparation et de séparation de liquide associés Ceased WO2018066341A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2016-197910 2016-10-06
JP2016197910A JP2018058795A (ja) 2016-10-06 2016-10-06 口腔用組成物、及びその製剤変色及び液分離の抑制方法

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021033662A1 (fr) * 2019-08-19 2021-02-25 小林製薬株式会社 Agent inhibiteur de la destruction du tissu gingival
WO2021033661A1 (fr) * 2019-08-19 2021-02-25 小林製薬株式会社 Activateur de cellules épithéliales gingivales
WO2024229402A3 (fr) * 2023-05-03 2025-01-30 Melaleuca, Inc. Boissons au collagène et procédés de fabrication et d'utilisation

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6882222B2 (ja) 2018-03-26 2021-06-02 Ｅｎｅｏｓ株式会社 水素充填システムの圧力計の故障診断方法及び水素充填システムの圧力計の校正方法

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5399339A (en) * 1977-02-09 1978-08-30 Sunstar Inc Tooth paste composition
JPH02292210A (ja) * 1989-05-08 1990-12-03 Lion Corp 口腔用組成物
JPH1112142A (ja) * 1997-06-19 1999-01-19 Lion Corp 口腔用組成物
JPH11286422A (ja) * 1998-03-31 1999-10-19 Lion Corp 口腔用組成物
JP2002114656A (ja) * 2000-10-05 2002-04-16 Nippon Zettoc Co Ltd 口腔用組成物用基剤及び口腔用組成物
JP2009263375A (ja) * 2002-07-29 2009-11-12 Warner-Lambert Co Llc トロポロン化合物および精油を含むオーラルケア組成物
JP2015127305A (ja) * 2013-12-27 2015-07-09 小林製薬株式会社 口腔用組成物
JP2017007991A (ja) * 2015-06-25 2017-01-12 ライオン株式会社 口腔用組成物及び該組成物におけるヒノキチオールの殺菌力向上方法

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5399339A (en) * 1977-02-09 1978-08-30 Sunstar Inc Tooth paste composition
JPH02292210A (ja) * 1989-05-08 1990-12-03 Lion Corp 口腔用組成物
JPH1112142A (ja) * 1997-06-19 1999-01-19 Lion Corp 口腔用組成物
JPH11286422A (ja) * 1998-03-31 1999-10-19 Lion Corp 口腔用組成物
JP2002114656A (ja) * 2000-10-05 2002-04-16 Nippon Zettoc Co Ltd 口腔用組成物用基剤及び口腔用組成物
JP2009263375A (ja) * 2002-07-29 2009-11-12 Warner-Lambert Co Llc トロポロン化合物および精油を含むオーラルケア組成物
JP2015127305A (ja) * 2013-12-27 2015-07-09 小林製薬株式会社 口腔用組成物
JP2017007991A (ja) * 2015-06-25 2017-01-12 ライオン株式会社 口腔用組成物及び該組成物におけるヒノキチオールの殺菌力向上方法

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021033662A1 (fr) * 2019-08-19 2021-02-25 小林製薬株式会社 Agent inhibiteur de la destruction du tissu gingival
WO2021033661A1 (fr) * 2019-08-19 2021-02-25 小林製薬株式会社 Activateur de cellules épithéliales gingivales
JP2021031405A (ja) * 2019-08-19 2021-03-01 小林製薬株式会社 歯肉上皮細胞活性化剤
JP2021031406A (ja) * 2019-08-19 2021-03-01 小林製薬株式会社 歯肉組織破壊抑制剤
JP7424769B2 (ja) 2019-08-19 2024-01-30 小林製薬株式会社 歯肉上皮細胞活性化剤
JP7424770B2 (ja) 2019-08-19 2024-01-30 小林製薬株式会社 歯肉組織破壊抑制剤
WO2024229402A3 (fr) * 2023-05-03 2025-01-30 Melaleuca, Inc. Boissons au collagène et procédés de fabrication et d'utilisation

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