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WO1999034773A1 - Compositions antimicrobiennes de soins bucco-dentaires a base de peroxyacide et methodes correspondantes - Google Patents

Compositions antimicrobiennes de soins bucco-dentaires a base de peroxyacide et methodes correspondantes Download PDF

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Publication number
WO1999034773A1
WO1999034773A1 PCT/US1999/000104 US9900104W WO9934773A1 WO 1999034773 A1 WO1999034773 A1 WO 1999034773A1 US 9900104 W US9900104 W US 9900104W WO 9934773 A1 WO9934773 A1 WO 9934773A1
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WIPO (PCT)
Prior art keywords
ion
composition
compositions
teeth
peroxy acid
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PCT/US1999/000104
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English (en)
Inventor
Satyanarayana Majeti
Original Assignee
The Procter & Gamble Company
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Application filed by The Procter & Gamble Company filed Critical The Procter & Gamble Company
Priority to CA002317067A priority Critical patent/CA2317067A1/fr
Priority to EP99900748A priority patent/EP1043970A1/fr
Publication of WO1999034773A1 publication Critical patent/WO1999034773A1/fr

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    • 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
    • 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
    • A61K8/30—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
    • A61K8/38—Percompounds, e.g. peracids

Definitions

  • compositions especially oral care compositions, including mouth rinses, toothpastes, gels, tooth powders, chewing gums, mouth sprays, lozenges (including breath mints), and sachets, comprising a peroxy acid compound and salts/esters thereof with an ion source such as chloride ion, bromide ion, thiocyanate ion, and/or iodide ion, source.
  • an ion source such as chloride ion, bromide ion, thiocyanate ion, and/or iodide ion, source.
  • this invention relates to topical compositions, especially oral care compositions resulting from the mixture of a peroxy acid compound and salts/esters thereof with an ion source such as chloride ion, bromide ion, thiocyanate ion, and/or iodide ion, source.
  • an ion source such as chloride ion, bromide ion, thiocyanate ion, and/or iodide ion, source.
  • This invention further relates to methods for treating or preventing topically- treatable microbial infections, especially diseases of the oral cavity, such as gingivitis, plaque, periodontal disease, and/or breath malodor, and/or for the whitening of teeth, in humans or other animals, by applying the above compositions to the oral cavity and/or teeth.
  • These compositions may further be used for treating or preventing topically-treatable microbial infections of the skin and mucous membranes.
  • Bacteria are a part of the normal flora of the body. They also are prevalent on all mucous membrane surfaces as indigenous flora. Given the proper circumstances and opportunity to penetrate tissues, microbes from the indigenous flora set up infections.
  • Periodontal disease is also an undesirable condition which has widespread occurrence.
  • Periodontal disease is a major cause of tooth loss in adults, beginning as early as age 35. Even by age 15, it is possible that 4 out of 5 persons already have gingivitis and possibly as many as 4 out of 10 have periodontitis.
  • Periodontal disease affects the periodontum, which is the investing and supporting tissues surrounding a tooth (i.e., the periodontal ligament, the gingiva, and the alveolar bone.)
  • Gingivitis and periodontitis are inflammatory disorders of the gingiva and the deeper periodontal tissues, respectively.
  • Periodontal disease is associated with the accumulation of plaque on the teeth.
  • the teeth are coated with a salivary proteanaceous material (pellicle) and thereafter streptococci adhere to this coating. Gingivitis occurs from the dental plaque, and periodontitis is caused by the infection- spreading to the periodontal pocket or space between the gingiva and the tooth root.
  • Teeth comprise both an inner dentin layer and an outer hard enamel layer.
  • the enamel layer protects the inner dentin layer and its live tissue and serves as the contact surface for mastication of solid food.
  • the enamel layer is generally translucent and slightly off-white in color. It is also considered porous since the hydroxy apatite crystals that comprise the enamel form microscopic hexagonal rods or prisms having microscopic pores or channels between them. As a result of this porous structure, staining agents and discoloring substances, such as antibiotics, foods containing coloring materials, coffee, cola, tea, tobacco, etc., can permeate the enamel and change its surface to appear yellow or brownish in color.
  • Microorganisms contribute to both the initiation and progression of gingivitis, plaque, periodontal disease, and/or breath malodor. Thus, in order to prevent or treat these conditions, these microorganisms must be suppressed by some means other than simple mechanical scrubbing. In addition, simple mechanical scrubbing will not be entirely effective to remove all stain types and/or to whiten the teeth.
  • BACKGROUND REFERENCES Peroxy acids, including monoperphthalate, used alone, are known in the art as bleaching agents in laundry applications and for tooth staining as well as for disinfecting/sterilizing hard surfaces, cloth diapers, removable orthodontic appliances, etc.
  • U.S. Pat. No. 4,490,269 issued Dec. 25, 1984, Gallopo, discloses cleansing compositions comprising an effervescent agent and a monoperphthalate, or an effervescent agent and potassium monopersulfate and a monoperphthalate, as bleaching agents. These compositions are used to clean removable orthodontic appliances such as false teeth, dental plates and bridges.
  • compositions generally in tablet form, containing a peroxygen compound (including monoperphthalate) and an effervescence generator.
  • compositions are dissolved in water to produce a bath in which to soak, and thereby cleanse, removable dentures.
  • references have disclosed monoperphthalic acid combined with H2O2, fluoride or bis-biquanide compounds.
  • compositions and methods for treating plaque, gingivitis, and periodontal disease comprising a substituted or unsubstituted_ monope ⁇ hthalate compound and a bis-biguanide compound (preferably chlorhexidine or alexidine).
  • a substituted or unsubstituted_ monope ⁇ hthalate compound preferably chlorhexidine or alexidine.
  • the combination of both compounds together or administered sequentially results in a synergistic benefit in anti-plaque activity and reduces staining of teeth caused by the bis-biguanide compound.
  • compositions and methods for treating microbial infections in the oral cavity the compositions comprising a monope ⁇ hthalic acid compound formulated into a rapidly dissolving powder matrix.
  • Prior art compositions have not been entirely satisfactory for the treatment and/or prevention of these skin and mucous membrane diseases, oral cavity diseases, oral malodor or for the whitening of teeth. Therefore, additional efficacious compositions and methods of treatment for these pu ⁇ oses are desirable.
  • the present invention relates to the su ⁇ rising discovery that when a peroxy acid compound or salts/esters thereof is used in combination with a chloride, bromide, thiocyanate, and/or iodide ion source, the compositions will be effective for the treatment or the prevention of topically-treatable microbial infections, especially diseases of the oral cavity, such as gingivitis, plaque, periodontal disease, and/or breath malodor, and/or for the whitening of teeth, in humans or other animals. It is the pu ⁇ ose of the present invention to provide topical compositions, especially oral care compositions (i.e.
  • mouth rinses toothpastes, gels, tooth powders, chewing gums, mouth sprays, lozenges, and sachets
  • a safe and effective amount of a peroxy acid compound, or pharmaceutically- acceptable salts or esters thereof comprising (or to provide topical compositions resulting from the mixture of): a.) a safe and effective amount of a peroxy acid compound, or pharmaceutically- acceptable salts or esters thereof; b.) a safe and effective amount of a chloride, bromide, thiocyanate, and/or iodide ion source; and c.) a pharmaceutically-acceptable, topical excipient.
  • compositions are effective in killing, and for a period of time suppressing the growth of, the microorganisms which cause topically-treatable infections, especially diseases of the oral cavity, such as plaque, gingivitis, periodontal disease, and breath malodor. These compositions are also effective to whiten teeth.
  • the present invention relates to compositions, especially shampoos, roll sticks, gels, creams, ointments, rinses, and oral care compositions such as mouth rinses, toothpastes, tooth powders, mouth sprays, chewing gums, lozenges (including breath mints), sachets, and bleaching kits, etc., for the treatment of topically-treatable microbial infections, comprising the reaction mixture of:
  • an ion source selected from the group consisting of a chloride ion, bromide ion, thiocyanate ion, iodide ion and mixtures thereof;
  • the present invention also relates to methods for treating or preventing topically-treatable microbial infections, especially diseases of the oral cavity, oral malodor, and to whiten teeth, in humans or other animals, by utilizing the above compositions.
  • These compositions are effective in killing, and for a period of time suppressing the growth of, the microorganisms which cause topically- treatable infections, especially diseases of the oral cavity, such as plaque, gingivitis, periodontal disease, and breath malodor.
  • These compositions are also effective to whiten teeth.
  • the present invention relates to compositions and methods of treating or preventing topically-treatable microbial infections, especially diseases of the oral cavity (e.g. plaque, gingivitis, periodontal disease), breath malodor, and for whitening teeth, in humans or other animals by topically applying to the tissue and/or teeth, a safe and effective amount of a peroxy acid compound or salts or esters thereof, combined with a safe and effective amount of a chloride, bromide, thiocyanate, and/or iodide ion source.
  • diseases of the oral cavity e.g. plaque, gingivitis, periodontal disease
  • breath malodor e.g., breath malodor, and for whitening teeth
  • topically-treatable anaerobe infections or “topically-treatable microbial infections”, as used herein, is meant tissue infections which are caused by or involve microorganisims, especially anaerobic bacteria, or otherwise, and may be treated by topical application.
  • tissue infections which are caused by or involve microorganisims, especially anaerobic bacteria, or otherwise, and may be treated by topical application.
  • the tissues that may be treated by topical application are external mucous membranes and mucocutaneous orifices.
  • Non-limiting examples of anaerobe infections that my be treated by topical application include anaerobe infections of the skin or soft tissue (e.g., acne, psoriasis, dandruff, gas gangrene (anaerobic myonecrosis), gas-forming cellulitis, perirectal abscess, breast abscess, dermatological lesions, wound infections, bovine mastitis), the vagina (e.g., - vulvovaginal abscess), the uterus (e.g. uterine infections), urinary tract infections, the eyes (e.g.
  • anaerobe infections of the skin or soft tissue e.g., acne, psoriasis, dandruff, gas gangrene (anaerobic myonecrosis), gas-forming cellulitis, perirectal abscess, breast abscess, dermatological lesions, wound infections, bovine mastitis
  • the vagina e.g.,
  • anaerobe infections that require enteral or systemic treatment methods to deliver the active to the infected tissue, such as abdominal infections, cardiovascular infections, central nervous system infections, lung infections, stomach and intestinal infections, and bone and joint infections.
  • Specific anaerobe infections are more fully disclosed in Finegold, Anaerobic Bacteria in Human Diseases. (Academic Press, Inc., New York, 1977), and in Anaerobic Bacteria, Role in Disease (published by Charles C.
  • topical skin diseases or infections include infections of bacterial, fungal, yeast, or viral origin as well as eczema, molds, warts, itching, bug bites, chicken pox, shingles, he ⁇ es simplex lesions, etc.
  • diseases of the oral cavity is meant diseases which are initiated and/or pe ⁇ etuated by bacteria in the oral cavity, especially anaerobic bacteria, and includes such diseases as, for example, periodontal disease, gingivitis, periodontitis, gingivosis, periodontosis, periodontitis complex, and other inflammatory and/or degenerative conditions of the tissues within the oral cavity, plus caries, Vincent's disease, trench mouth, oral malodor, he ⁇ es simplex lesions, and apthous ulcers.
  • dentoalveolar infections are dentoalveolar infections, dental abscesses (e.g., cellulitis of the jaw; osteomyelitis of the jaw), acute necrotizing ulcerative gingivitis (i.e., Vincent's infection), infectious stomatitis (i.e., acute inflammation of the buccal mucosa), and Noma (i.e., gangrenous stomatitis or cancrum oris).
  • Oral and dental infections are more fully disclosed in Finegold, Anaerobic Bacteria in Human Diseases, chapter 4, pp. 78-104, and chapter 6, pp. 115-154 (Academic Press, Inc., NY, 1977), the disclosures of which are inco ⁇ orated herein by reference in their entirety.
  • the compositions and methods of treatment of the present invention are particularly effective for treating or preventing periodontal disease (gingivitis and/or periodontitis) and breath malodor.
  • safe and effective amount as used herein is meant an amount of a peroxy acid compound, or a pharmaceutically-acceptable salt or ester thereof, and/or an amount of ion source, high enough to significantly (positively) modify the condition to be treated or to effect the desired whitening result, but low enough to avoid serious side effects (at a reasonable benefit/risk ratio), within the scope of sound medical judgment.
  • the safe and effective amount will vary with the particular condition (e.g., disease of the oral cavity or malodor, etc.) being treated the age and physical condition of the patient being treated, the severity of the condition, malodor or staining of the teeth, etc. the duration of treatment, the nature of concurrent therapy, the specific form (i.e., acid, salt, and/or ester) of the compound or ion employed, and the particular vehicle from which the compound or ion is applied.
  • teethpaste as used herein is meant paste, powder, and gel formulations unless otherwise specified.
  • oral care composition or “oral composition” as used herein is meant a product which is not intentionally swallowed for pu ⁇ oses of systemic administration of therapeutic agents, but is retained in the oral cavity for a sufficient time to contact substantially all or some of the dental surfaces and/or oral mucosal tissues for pu ⁇ oses of oral activity.
  • the present invention relates to compositions or methods utilizing peroxy acids whose efficacy and stability are enhanced by the addition of a source of bromide ion, iodide ion, chloride ion and/or thiocyanate ion.
  • compositions of the present invention comprise a safe and effective amount of peroxy acid compound.
  • compositions of the present invention comprise from about 0.1% to about 25 %, by weight of the composition, more preferably from about 0.5% to about 15 %, even more preferably from about 1% to about 10%, by weight of the composition, of a peroxy acid compound.
  • the peroxy acid compound of the present invention is any compound with a peroxy acid functionality which may be an organic or inorganic compound and contains a mono, di, tri, or poly peroxy acid functionality, or salts or esters thereof.
  • peroxy acid compounds of the present invention are known in the art. These compounds are disclosed in e.g. U.S. Pat. Nos. 3,075,921, Brockelhurst et al., issued Jan. 29, 1963, U.S. 3,749,674, issued July 31, 1973, U.S. 3,988,433, issued Oct. 26, 1976, Benedict; and U.S. 4,990,329, issued Feb. 5, 1991, Sampathkumar, all of which are herein inco ⁇ orated by reference in their entirety.
  • Preferred peroxy acid compounds of the present invention include alkyl - diperoxyacid with alkylene groups containing from 5 to 11 alkyl groups including substituted alkyl groups, i.e.
  • alkyl diperoxyacids those with up to 2 substituents selected from the group consisting of chloro, fluoro, nitro, trifluoromethyl, trimethylammonium, carboxy, and acetyl groups, per methylene group.
  • substituents selected from the group consisting of chloro, fluoro, nitro, trifluoromethyl, trimethylammonium, carboxy, and acetyl groups, per methylene group.
  • Unsubstituted alkyl diperoxyacids are preferred alkyl diperoxyacids.
  • the peroxy acid compound of the present invention are preferably the 1,12- dodecanedioic peroxy acid-based agents which may be unsubstituted or substituted.
  • the substituted 1,12-dodecanedioic peroxy acid agents may be substituted with one or more substitutes selected from the group consisting of straight or branched chain alkyl groups having from 1 to about 6 carbon atoms (preferably methyl or ethyl), phenyl, benzyl, chloro, fluoro, nitro, trifluoromethyl, trialkylammonium (e.g., trimethylammonium, triethylammonium), — CO 2 H, — CO 3 H, or mixtures thereof.
  • no more than about two of the carbon atoms in the 1,12-dodecanedioic acid chain is substituted.
  • the 1,12-dodecanedioic acid chain is unsubstituted (i.e., — (CH 2 ) 10 — ). It is further preferred that the 1,12-dodecanedioic acid agent be the diperoxy acid (i.e., HO 3 C(CH 2 ) ⁇ oCO 3 H.) But a peroxy acid of unsubstituted or substituted 1,12-dodecanedioic acid may also be a compound having only one peroxy acid group per molecule at either the 1 or 12 position, provided there is a carboxy lie acid or carboxylate group at the other end of the carbon chain, e.g., HO 2 C(CH 2 ) ⁇ oCO 3 H.
  • compositions herein may also comprise mixtures of diperoxy and monoperoxy 1,12-dodecanedioic acid, and/or the pharmaceutically- acceptable salts or esters of such acids.
  • the 1,12-dodecanedioic peroxy acid agents of the present invention are known compounds, and they may be synthesized by known methods. Such known methods and peroxy acids are disclosed in, e.g., U.S. Pat. No. 4,483, 781, to Hartman, issued Nov. 20, 1984; and in U.S. Pat. No. 3,988,433, to Benedict, issued Oct. 26, 1976. The disclosures of both these patents are inco ⁇ orated herein by reference in their entirety.
  • the preferred peroxy acid compounds of the present invention also include compounds having the general structure:
  • substituents compatible with the peroxy acid functionality of the aromatic ring is meant substituents on the ring which do not react with peroxy acid groups, thereby reducing the stability and effectiveness of the compounds, for the treatment of diseases of the skin, mucous membranes, oral cavity, breath malodor, and for teeth whitening.
  • R is hydrogen, substituted and unsubstituted saturated alkyl having from 1 to 20 carbon atoms (e.g., methyl, ethyl), substituted and unsubstituted aryl (e.g., phenyl, naphthyl), substituted and unsubstituted benzyl, chloro, fluoro, nitro, sulphonate, trifluoromethyl, trialkylammonium (e.g., trimethylammonium; triethylammonium), cyano, carboxy, carboxylate (e.g., -O-COCH3), percarboxylate (e.g., -CO3H), alkoxy (e.g., methoxy, ethoxy), iodo, bromo, substituted or unsubstituted amino, or amido group.
  • aryl e.g., phenyl, naphthyl
  • esters and salts of the substituted or unsubstituted peroxy acid compounds which have the same general antimicrobial properties, and which are acceptable from a toxicity viewpoint.
  • Nonlimiting examples of pharmaceutically-acceptable salts include alkali metal (e.g., sodium, potassium), alkaline earth metal (e.g., calcium, magnesium), non-toxic heavy metal, and trialkyl ammonium (e.g., trimethylammonium).
  • Preferred salts include divalent cations (e.g., magnesium, calcium).
  • Peroxy acid compounds, especially magnesium monope ⁇ hthalate, are also_ disclosed in U.S. Pat. Nos. 4,990,329, issued Feb.
  • Synthesis of substituted and unsubstituted monope ⁇ hthalic acid compounds can be achieved by those skilled in the art using methods disclosed in, for example, European Patent Application No. 27,693, published April 29, 1981, filed by Interox Chemicals Limited; European Patent Application No. 66,992, to Interox Chemicals Limited; U.S. Pat. No. 3,075,921, to Brockelhurst et al.; "Organic Peroxides," Daniel Swern, Editor, published 1970 by John Wiley & Sons, Inc.; and in British Patent Specification No. 1,378,671; the disclosures of all of which are inco ⁇ orated herein by reference in their entirety. Synthesis of the magnesium salt of monope ⁇ hthalic acid is disclosed in the European Patent Application No. 27,693, cited above. This compound is also commercially available from Interox Chemicals Limited.
  • compositions and methods of the present invention also comprise a safe and effective amount of an ion source.
  • the present invention also comprises a source of bromide ion, chloride ion, iodide ion, and/or thiocyanate ion, and mixtures thereof.
  • the ion source can be any salt of the above ions including alkali metal (e.g., sodium, potassium), alkaline earth metal (e.g., calcium, magnesium), non-toxic heavy metal, ammonium, e.g. trialkyl ammonium (e.g., trimethylammonium) and amines.
  • alkali metal e.g., sodium, potassium
  • alkaline earth metal e.g., calcium, magnesium
  • non-toxic heavy metal e.g. trialkyl ammonium (e.g., trimethylammonium) and amines.
  • An especially preferred ion source is NaCl.
  • compositions of the present invention comprise a safe and effective amount of the above ion source, preferably from about 0.01% to about 25 % by weight of the composition, more preferably from about 0.05% to about 15 %, even more preferably from about 0.5% to about 10%, by weight of the composition.
  • halogen compounds include sodium hypochlorite, hypochlorous acid, N- chlorosuccinimide, sodium hypobromite, N-bromosuccinimide, N-iodosuccinimide, etc.
  • compositions are capable of being commingled without interaction in a manner which would substantially reduce the composition's stability and/or efficacy for treating or preventing topically-treatable microbial infections, especially diseases of the oral cavity including plaque, gingivitis, periodontal disease, as well as breath malodor and to whiten the teeth, according to the method/composition of the present invention.
  • the carrier be buffered, or contain a buffer, capable of maintaining the pH of the oral cavity during use from about pH 4 to about pH 8, more preferred being pH from about 5.0 to about 7.5.
  • buffers include citrate, citrate/bicarbonate and phosphate buffers.
  • the excipients or carriers of the present invention can include the usual and conventional components of skin care compositions such as shampoos, creams, ointments, rinses, roll-sticks, gels and oral care compositions such as toothpastes (including gels and tooth powders), mouth rinses, mouth sprays, chewing gums, lozenges (including breath mints), and sachets.
  • skin care compositions such as shampoos, creams, ointments, rinses, roll-sticks, gels and oral care compositions such as toothpastes (including gels and tooth powders), mouth rinses, mouth sprays, chewing gums, lozenges (including breath mints), and sachets.
  • These conventional components include flavors, perfumes, thickeners, humectants, abrasive, surfactants, water, alcohol, fluoride, etc.
  • an oral carrier to be used is basically determined by the way the composition is to be introduced into the oral cavity. If a toothpaste (including gels, etc.) is to be used, then a "toothpaste carrier" is chosen as disclosed in, e.g., U.S. Pat. No. 3,988,433, to Benedict, the disclosure of which is inco ⁇ orated herein by reference (e.g., abrasive materials, sudsing agents, binders, humectants, flavoring and sweetening agents, etc.). If a mouth rinse is to be used, then a "mouth rinse carrier" is chosen, as disclosed in, e.g., U.S. Pat. No.
  • Carriers suitable for the preparation of compositions of the present invention are well known in the art. Their selection will depend on secondary considerations like taste, cost, and shelf stability, etc.
  • compositions of the subject invention are in the form of dentifrices, such as toothpastes, tooth gels and tooth powders.
  • Components of such toothpaste and tooth gels generally include one or more of a dental abrasive (from about 10% to about 50%), a surfactant (from about 0.5% to about 10%), a thickening agent (from about 0.1% to about 5%), a humectant (from about 10% to about 55%), a flavoring agent (from about 0.04% to about 2%), a sweetening agent (from about 0.1% to about 3%), a coloring agent (from about 0.01% to about 0.5%) and water (from about 2% to about 45%).
  • a dental abrasive from about 10% to about 50%
  • a surfactant from about 0.5% to about 10%
  • a thickening agent from about 0.1% to about 5%
  • a humectant from about 10% to about 55%)
  • a flavoring agent from about 0.04% to about 2%
  • Such toothpaste or gel may also include one or more of an anticaries agent (from about 0.05% to about 0.3% as fluoride ion), and an anticalculus agent (from about 0.1% to about 13%). Tooth powders, of course, contain substantially all non-liquid components.
  • compositions of the subject invention are mouthwashes and mouth sprays.
  • Components of such mouthwashes and mouth sprays typically include one or more of water (from about 45% to about 95%), ethanol (from about 0% to about 25%), a humectant (from about 0% to about 50%), a surfactant (from about 0.01% to about 7%), a flavoring agent (from about 0.04% to about 2%), a sweetening agent (from about 0.1% to about 3%), and a coloring agent (from about 0.001% to about 0.5%).
  • Such mouthwashes and mouth sprays may also include one or more of an anticaries agent (from about 0.05% to about 0.3% as fluoride ion), and an anticalculus agent (from about 0.1% to about 3%).
  • compositions of the subject invention are dental solutions.
  • Components of such dental solutions generally include one or more of water (from about 90% to about 99%), preservative (from about 0.01% to about 0.5%), thickening agent (from 0% to about 5%), flavoring agent (from about 0.04% to about 2%), sweetening agent (from about 0.1% to about 3%), and surfactant (from 0% to about 5%).
  • Oral gel compositions typically include one or more of water (from 0% to _ about 99%), a humectant such as glycerin, (from 0% to about 99%), a thickening agent (from about 0.1% to about 20%), a flavoring agent (from about 0.04% to abut 2%), and a sweetening agent (from about 0.01% to about 0.5%).
  • Chewing gum compositions typically include one or more of a gum base
  • Lozenges are discoid-shaped solids comprising a therapeutic agent in a flavored base.
  • the base may be a hard sugar candy, glycerinated gelatin or combination of sugar with sufficient mucilage to give it form. These dosage forms are generally described in Remington: The Science and Practice of Pharmacy, 19 th Ed., Vol. II, Chapter 92, 1995.
  • Lozenge compositions typically include one or more fillers (compressible sugar), flavoring agents, and lubricants.
  • the term "lozenge” as used herein includes: breath mints, troches, pastilles, and microcapsules. Microcapsules of the type contemplated herein are disclosed in U.S. Pat. No. 5,370,864, Peterson et al., issued Dec. 6, 1994, which is herein inco ⁇ orated by reference in its entirety.
  • compositions of the present invention are:
  • Dental abrasives useful in the topical, oral carriers of the compositions of the subject invention include many different materials.
  • the material selected must be one which is compatible within the composition of interest and does not excessively abrade dentin.
  • Suitable abrasives include, for example, silicas including gels and precipitates, insoluble sodium polymetaphosphate, hydrated alumina, calcium carbonate, dicalcium orthophosphate dihydrate, calcium pyrophosphate, tricalcium phosphate, calcium polymetaphosphate, and resinous abrasive materials such as particulate condensation products of urea and formaldehyde.
  • abrasives for use in the present compositions is the particulate thermo-setting polymerized resins as described in U.S. Pat. No. 3,070,510 issued to Cooley & Grabenstetter on Dec. 25, 1962.
  • Suitable resins include, for example, melamines, phenolics, ureas, melamine-ureas, melamine- formaldehydes, urea-formaldehyde, melamine-urea-formaldehydes, cross-linked epoxides, and cross-linked polyesters. Mixtures of abrasives may also be used.
  • Silica dental abrasives of various types are preferred because of their unique - benefits of exceptional dental cleaning and polishing performance without unduly abrading tooth enamel or dentine.
  • the silica abrasive polishing materials herein, as well as other abrasives generally have an average particle size ranging between about 0.1 to about 30 microns, and preferably from about 5 to about 15 microns.
  • the abrasive can be precipitated silica or silica gels such as the silica xerogels described in Pader et al., U.S. Patent 3,538,230, issued Mar. 2, 1970, and DiGiulio, U.S. Patent 3,862,307, issued Jan. 21, 1975, both inco ⁇ orated herein by reference.
  • silica xerogels marketed under the trade name "Syloid" by the W.R. Grace & Company, Davison Chemical Division.
  • precipitated silica materials such as those marketed by the J. M. Huber Co ⁇ oration under the trade name, Zeodent®, particularly the silica carrying the designation Zeodent 119®.
  • Zeodent® particularly the silica carrying the designation Zeodent 119®.
  • the types of silica dental abrasives useful in the toothpastes of the present invention are described in more detail in Wason, U.S. Patent 4,340,583, issued July 29, 1982.
  • the abrasive in the toothpaste compositions described herein is generally present at a level of from about 6% to about 70% by weight of the composition.
  • toothpastes contain from about 10% to about 50% of abrasive, by weight of the composition.
  • a particularly preferred precipitated silica is the silica disclosed in US Pat. Nos. 5,603,920, issued on Feb. 18, 1997; 5,589,160, issued Dec. 31, 1996; 5,658,553, issued Aug. 19, 1997; 5,651,958, issued July 29, 1997, all of which are assigned to the Procter & Gamble Co. All of these patents are inco ⁇ orated herein by reference in their entirety.
  • abrasives can be used. All of the above patents regarding dental abrasives are inco ⁇ orated herein by reference.
  • the total amount of abrasive in dentifrice compositions of the subject invention preferably range from about 6% to about 70% by weight; toothpastes preferably contain from about 10% to about 50% of abrasives, by weight of the composition.
  • Solution, mouth spray, mouthwash and oral gel compositions of the subject invention typically contain no abrasive.
  • Suitable sudsing agents are those which are reasonably stable and form foam throughout a wide pH range, preferably nonsoap anionic organic synthetic detergents.
  • examples of such agents are water-soluble salts of alkyl sulfate having from 10 to 18 carbon atoms in the alkyl radical, such as sodium lauryl sulfate.
  • detergents include water-soluble salts of sulfonated monoglycerides of fatty acids having from 10 to 18 carbon atoms, such as sodium monoglyceride sulfonates; salts of CJ O to C ⁇ g fatty acid amides of taurine, such as sodium N-methyl-N-palmitoyl tauride; salts of C10 to Cjg fatty acid esters of isethionic acid; and substantially saturated aliphatic acyl amides of saturated monoaminocarboxylic acids having 2 to 6 carbon atoms and in which the acyl radical contains 12 to 16 carbon atoms, such as sodium N-lauroyl sarcoside.
  • Suitable sudsing agents include the nonionic, cationic, zwitterionic and amphoteric nonsoap organic synthetic detergents.
  • the sudsing agent can be present in the dentifrice compositions of this invention in an amount from about 0.5% to about 10%, preferably from about 1% to about 5%, by weight of the total composition.
  • Fluoride Ions The present invention may also inco ⁇ orate free fluoride ions.
  • Preferred free fluoride ions can be provided by sodium fluoride, stannous fluoride, indium fluoride, and sodium monofluorophosphate.
  • Sodium fluoride is the most preferred free fluoride ion.
  • the present composition may contain from about 50 ppm to about 3500 ppm, and preferably from about 500 ppm to about 3000 ppm of free fluoride ions.
  • thickening Agents are carboxyvinyl polymers, carrageenan, hydroxyethyl cellulose, laponite and water soluble salts of cellulose ethers such as sodium carboxymethylcellulose and sodium carboxymethyl hydroxyethyl cellulose.
  • Natural gums such as gum karaya, xanthan gum, gum arabic, and gum tragacanth can also be used.
  • Colloidal magnesium aluminum silicate or finely divided silica can be used as part of the thickening agent to further improve texture.
  • a preferred class of thickening or gelling agents includes a class of homopolymers of acrylic acid crosslinked with an alkyl ether of pentaerythritol or an alkyl ether of sucrose, or carbomers.
  • Carbomers are commercially available from B.F. Goodrich as the Carbopol® series.
  • Copolymers of lactide and glycolide monomers, the copolymer having the - molecular weight in the range of from about 1,000 to about 120,000 (number average), are useful for delivery of actives into the periodontal pockets or around the periodontal pockets as a "subgingival gel carrier.” These polymers are described in U.S. Pat. Nos.
  • Thickening agents in an amount from about 0.1% to about 15%, preferably from about 2% to about 10%, more preferably from about 4% to about 8%, by weight of the total toothpaste or gel composition, can be used. Higher concentrations can be used for chewing gums, lozenges (including breath mints), sachets, and subgingival gels.
  • Humectants Another optional component of the topical, oral carriers of the compositions of the subject invention is a humectant.
  • the humectant serves to keep compositions from hardening upon exposure to air, to give compositions a moist feel to the mouth, and, for particular humectants, to impart desirable sweetness of flavor to toothpaste compositions.
  • the humectant, on a pure humectant basis, generally comprises from about 0% to about 70%, preferably from about 5% to about 25%, by weight of the compositions herein.
  • Suitable humectants for use in compositions of the subject invention include edible polyhydric alcohols such as glycerin, sorbitol, xylitol, butylene glycol, polyethylene glycol, and propylene glycol, especially sorbitol and glycerin.
  • Flavoring agents can also be added to the compositions. Suitable flavoring agents include oil of wintergreen, oil of peppermint, oil of spearmint, clove bud oil, menthol, anethole, methyl salicylate, eucalyptol, cassia, 1-menthyl acetate, sage, eugenol, parsley oil, oxanone, alpha-irisone, marjoram, lemon, orange, propenyl guaethol, cinnamon, vanillin, thymol, linalool, cinnamaldehyde glycerol acetal known as CGA, and mixtures thereof.
  • Suitable flavoring agents include oil of wintergreen, oil of peppermint, oil of spearmint, clove bud oil, menthol, anethole, methyl salicylate, eucalyptol, cassia, 1-menthyl acetate, sage, eugenol, parsley oil, oxan
  • Flavoring agents are generally used in the compositions at levels of from about 0.001% to about 5%, by weight of the composition.
  • Sweetening agents which can be used include sucrose, glycose, saccharin, dextrose, levulose, lactose, mannitol, sorbitol, fructose, maltose, xylitol, saccharin salts, thaumatin, aspartame, D-tryptophan, dihydrochalcones, acesulfame and cyclamate salts, especially sodium cyclamate and sodium saccharin, and mixtures - thereof.
  • a composition preferably contains from about 0.1% to about 10% of these agents, preferably from about 0.1% to about 1%, by weight of the composition.
  • compositions of the present invention can be used as optional ingredients in compositions of the present invention. These agents are present in the compositions at a level of from about 0.001% to about 10%, preferably from about 0.1% to about
  • the coolant can be any of a wide variety of materials. Included among such materials are carboxamides, menthol, ketals, diols, and mixtures thereof.
  • Preferred coolants in the present compositions are the paramenthan carboxyamide agents such as N-ethyl-p-menthan-3-carboxamide, known commercially as "WS-3", N,2,3- trimethyl-2-isopropylbutanamide, known as "WS-23,” and mixtures thereof.
  • Additional preferred coolants are selected from the group consisting of menthol, 3-1- menthoxypropane-l,2-diol known as TK-10 manufactured by Takasago, menthone glycerol acetal known as MGA manufactured by Haarmann and Reimer, and menthyl lactate known as Frescolat® manufactured by Haarmann and Reimer.
  • menthol and menthyl as used herein include dextro- and levorotatory isomers of these compounds and racemic mixtures thereof.
  • TK-10 is described in U.S. Pat. No. 4,459,425, Amano et al, issued 7/10/84.
  • WS-3 and other agents are described in U.S. Pat. No. 4,136,163, Watson, et al, issued Jan. 23, 1979; the disclosure of both are herein inco ⁇ orated by reference in their entirety.
  • Preferred salivating agents of the present invention include Jambu® manufactured by Takasago.
  • Preferred warming agents include capsicum and nicotinate esters, such as benzyl nicotinate.
  • Preferred numbing agents include benzocaine, lidocaine, clove bud oil, and ethanol.
  • compositions (or reaction mixture thereof) of the present invention may be topically applied to the skin, mucous membranes, mucosal or gingival tissue of the oral cavity, or to the surface of the teeth, in several conventional ways.
  • the skin, gingival tissue or teeth may be rinsed with a solution (e.g., rinse, spray).
  • the gingival tissue or teeth may be brushed with a dentifrice (e.g., toothpaste, gel or tooth powder), where the gingival tissue or teeth are bathed in the liquid and/or lather generated by brushing the teeth.
  • a dentifrice e.g., toothpaste, gel or tooth powder
  • the skin, mucous membrane, gingival tissue or teeth may be directly covered with a gel or paste.
  • the gingival tissue or teeth may be bathed in liquid generated by chewing gum, chewing tablets, or sucking on a lozenge or sachet.
  • Other methods of topically applying the present composition (or reaction mix) to the skin, mucous membranes, gingival tissue and/or the surfaces of the teeth are apparent to those skilled in the art.
  • buffering e.g., the oral cavity
  • Non-limiting examples of pharmaceutically-acceptable buffers include citrate, citrate/bicarbonate and phosphate buffers. It is also preferred that, in the method of treating diseases of the oral cavity of the present invention, the composition (or reaction mix) not be intentionally ingested.
  • compositions of the present invention are obtained by the combination of two phases, the first phase comprising a compound with a peroxy acid functionality and the second phase comprising an ion source such as salts of chloride, thiocyanate, bromide or iodide.
  • these two phases can be mixed just prior to use, for example from about 5 to about 60 minutes prior to use by the consumer.
  • the two phases can be combined during use of the composition by the consumer.
  • the two phase are combined prior to use, so that the pH of the final composition can be adjusted (from about pH 5 to 8) for maximum effectiveness.
  • a safe and effective amount of the present composition is preferably applied (as a cream, gel, spray, or shampoo, etc.) to the affected tissue for at least about 10 seconds, preferably from about 20 seconds to about 10 minutes, about once per day to about 4 times per day, preferably about two times per day, for a duration of about one week to about 2 weeks or until the condition is cleared.
  • a safe and effective amount of the present composition is preferably applied (by rinsing with a solution, directly applying a gel, applying a gel with a toothbrush, plastic strip as described below, etc.) to the gingival tissue preferably for at least about 10 seconds, preferably from about 20 seconds to about 10 minutes, more preferably from about 30 seconds to about 60 seconds.
  • the method often involves expectoration of most of the compositions following such contact, preferably followed with rinsing, e.g. with water.
  • the frequency of such contact is preferably from about once per week to about four times per day, more preferably from about thrice per week to about three times per day, even more preferably from about once per day to about twice per day.
  • the period of such treatment typically ranges from about one day to a lifetime.
  • the duration of treatment is preferably from about 7 days to about 6 months, preferably from about 3 to about 6 months, but may be shorter or longer depending on the severity of the oral disease being treated, the particular delivery form utilized and the patient's response to treatment.
  • diseases of the oral cavity can include oral soft tissue infection such as he ⁇ es simplex virus, apthous ulcers, etc.
  • the composition ( or reaction mix) is applied on an as needed basis, possibly up to 5-6 times per day.
  • a safe and effective amount of the present composition (or reaction mix) is preferably applied (without or with an oral appliance, e.g. toothbrush, tray containing the composition, plastic strips, etc.) to the teeth preferably for at least about 10 seconds, preferably from about 20 seconds to about 10 minutes, more preferably from about 30 seconds to about 60 seconds.
  • an oral appliance e.g. toothbrush, tray containing the composition, plastic strips, etc.
  • the exact procedure to be used depends on whether the bleaching is performed by a dentist in the office, under the supervision of a dentist, or is performed directly by the consumer.
  • the dentist makes a tooth tray using deformable plastic to fit the patient's teeth. Then an appropriate amount of the present composition (or reaction mix) is added to the tray.
  • the patient wears the tray for a period of about 10 minutes to about 8 hours, each day for a period of 7 to 28 days or for as long as needed to get the desired whitening effect.
  • the patient may repeat this procedure as needed to whiten their teeth.
  • the consumer can purchase a generic plastic mouth tray, to be soaked in hot water for 15 minutes until soft. Then consumer bites into the tray to make an impression of their teeth.
  • the self formed trays are then used to carry the present composition.
  • the consumer applies to their teeth, a thin plastic film pre-coated with the present bleaching composition, and wears it for a period of about 10 minutes to about 8 hours as described above.
  • the consumer uses a new strip for each application of the bleaching composition.
  • strip appliance is further described in P&G Copending Applications Serial Nos. 08/870,664, 08/870,330, 08/870,331 and 08/870,665 all filed on June 6, 1997, the disclosure of which are herein inco ⁇ orated by reference in their entirety.
  • Other consumer in-home-use methods include brushing the present composition (or reaction mix) on the teeth or rinsing with a mouthrinse in the same manner as described above for the method of treating diseases of the oral cavity.
  • the present invention further relates to compositions for use in the methods of treatments according to the present invention.
  • the present invention further relates to skin composition such as shampoos, roll sticks, gels, rinses, and oral care compositions especially mouth rinses, toothpastes, tooth powders, mouth sprays, chewing gums, lozenges, sachets, and bleaching kits, comprising the reaction mixture of:
  • a composition, for application to oral care tissues, teeth, or skin, having two phases (a) and (b) have the following components:
  • phase (a) independently formulate phases (a) and (b).
  • Formulate phase (a) by combining the bicarbonate and monosodium phosphate and mix until homogeneous . Thereafter add citric acid and mix until homogeneous. Add the remaining ingredients except MMPP . Mix until homogeneous and add the MMPP.
  • the MMPP may be suspended in an unreactive organic matrix at the desired concentration using ingredients such as mineral oil, petrolatum or a mixture thereof.
  • Formulate phase (b) by combining glycerin and CMC and mix until homogeneous. Thereafter add sorbitol and mix until homogeneous. Add xanthan gum along with citrate/citric acid and mix until homogeneous. Finally add sodium chloride and magnesium sulfate.
  • the two phases prepared as above can be used to formulate a variety of products.
  • the resulting gel can be used for whitening teeth in a tray or other device.
  • the proportion of formulation (a) can be suitably increased up to a ratio of 2:1.
  • this mixed gel can be further formulated into a toothpaste by admixing 5-10% silica, SLS and titanium dioxide.
  • Sodium fluoride can be optionally added to phase (b) for a toothpaste composition as well.
  • the level of the MMPP in the toothpaste composition may be 10-20%.
  • 2 gms of the 1:1 gel composition may be dispersed in 15 ml of water, prior to rinsing the oral cavity.
  • this gel matrix thus generated can be formulated into shampoos by combining from 5-50% of the gel preparation by weight with 95-50% of a typical
  • the gel matrix generated above can be formulated into skin lotions, dermatological sprays, hand soaps, mouth rinses, and other compositions by using agents that are typically found in these product forms.

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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)
  • Oral & Maxillofacial Surgery (AREA)
  • Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
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  • Cosmetics (AREA)

Abstract

La présente invention concerne des compositions, spécialement des shampooings, des déodorants à bille, des gels, des solutions de rinçage, ainsi que des produits de soins bucco-dentaires tels que les solutions dentaires, les dentifrices, les poudres dentifrices, les sprays dentaires, des gommes à mâcher, des pastilles, des sachets et des nécessaires de blanchiment etc.., destinés au traitement des infections microbiennes pouvant se traiter localement, ces compositions comprenant un mélange de: (1) une quantité efficace et inoffensive d'un composé de peroxyacide, ou de sels ou d'esters pharmaceutiquement acceptables de celui-ci, (2) une quantité efficace et inoffensive d'une source ionique sélectionnée dans le groupe constitué par des ions chlorure, des ions bromure, des ions iodure, des ions thiocyanate, ainsi que des mélanges de ces ions, et enfin, (3) un excipient local pharmaceutiquement acceptable. Par ailleurs, cette invention, concerne des méthodes de traitement ou de prévention des infections microbiennes pouvant être traitées localement, particulièrement les infections de la cavité buccale, la mauvaise haleine, et de blanchiment des dents, chez les humains ou les animaux, en utilisant les compositions susmentionnées. Ces compositions sont efficaces pour tuer, ou réduire la prolifération pendant un certain temps, des micro-organismes qui sont à l'origine des infections pouvant se traiter localement, particulièrement les infections de la cavité buccale, telles que la plaque dentaire, les gingivites, les infections périodentales et la mauvaise haleine. Ces compositions sont également efficace pour blanchir les dents.
PCT/US1999/000104 1998-01-06 1999-01-05 Compositions antimicrobiennes de soins bucco-dentaires a base de peroxyacide et methodes correspondantes WO1999034773A1 (fr)

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CA002317067A CA2317067A1 (fr) 1998-01-06 1999-01-05 Compositions antimicrobiennes de soins bucco-dentaires a base de peroxyacide et methodes correspondantes
EP99900748A EP1043970A1 (fr) 1998-01-06 1999-01-05 Compositions antimicrobiennes de soins bucco-dentaires a base de peroxyacide et methodes correspondantes

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Cited By (16)

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US6264924B1 (en) * 1998-02-27 2001-07-24 The Procter & Gamble Company Oral care compositions comprising chlorite and methods
WO2003000216A1 (fr) * 2001-06-23 2003-01-03 Lg Household & Health Care Ltd. Pastilles multicouches pour blanchiment dentaire
GB2402621A (en) * 2003-06-09 2004-12-15 Sharron Marsden Lollipop/sweet for dental hygiene purposes
WO2006002287A1 (fr) * 2004-06-23 2006-01-05 Hofmann Robert F Utilisation de preparation therapeutique oxydative ciblee dans un traitement endodontique
CH707698A1 (de) * 2013-03-12 2014-09-15 Bonyf Ag Pharmazeutisches Mittel zur Behandlung von Schleimhautentzündungen.
CH710357A1 (de) * 2014-11-11 2016-05-13 Bogaert Jean-Pierre Kosmetisches und pharmazeutisches Mittel zur Behandlung von Hautrissen.
US9833471B1 (en) 2016-09-15 2017-12-05 Reoxcyn Discoveries Group, Inc. Hypochlorous acid-based hand sanitizer
WO2018031922A1 (fr) * 2016-08-11 2018-02-15 Sulfilatec, Inc. Compositions médicales et nutritionnelles et méthodes d'utilisation
EP3342394A1 (fr) * 2016-12-28 2018-07-04 Stephane Bochenek Gel de blanchiment dentaire sur base naturelle et sans peroxydes
US10471003B2 (en) 2016-05-18 2019-11-12 Reoxcyn, Llc Lubricant formulations
US10485827B2 (en) 2016-01-19 2019-11-26 Rdg Holdings, Inc. Topical eye serum compositions, methods or preparing, and methods of use
US10543230B2 (en) 2013-10-07 2020-01-28 Rdg Holding, Inc. Redox signaling gel formulation
US11211249B2 (en) 2008-03-06 2021-12-28 Sensient Flavors Llc Herbal extracts and flavor systems for oral products and methods of making the same
US11376278B2 (en) 2016-08-11 2022-07-05 Sulfilatec, Inc. Compositions and methods for treating disease
US11583481B2 (en) 2017-01-16 2023-02-21 Reoxcyn, Llc Dentifrice formulations and methods of oral care
US11857674B2 (en) 2016-05-18 2024-01-02 Reoxcyn, Llc Lubricant formulations

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DE102004005788A1 (de) * 2004-02-06 2005-09-01 Riemser Arzneimittel Ag Zubereitungen enthaltend Echinacea-Auszüge und Thiocyanat

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US2218172A (en) * 1934-10-13 1940-10-15 Autoxygen Inc Preparation for antisepsis of the oral cavity
FR2627084A1 (fr) * 1988-02-11 1989-08-18 Rcd Labo Sarl Formes galeniques solides contenant une ou plusieurs substances peroxydiques liberant de l'oxygene actif et utilisees en hygiene bucco-dentaire ou comme decontaminants de lentilles ophtalmiques
WO1997007777A1 (fr) * 1995-08-15 1997-03-06 Robert Eric Montgomery Compositions orales activant la peroxydase
DE19710068A1 (de) * 1997-03-12 1998-09-17 Kramer Axel Mittel zur Förderung der Mundhygiene und der Mundgesundheit

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US2218172A (en) * 1934-10-13 1940-10-15 Autoxygen Inc Preparation for antisepsis of the oral cavity
FR2627084A1 (fr) * 1988-02-11 1989-08-18 Rcd Labo Sarl Formes galeniques solides contenant une ou plusieurs substances peroxydiques liberant de l'oxygene actif et utilisees en hygiene bucco-dentaire ou comme decontaminants de lentilles ophtalmiques
WO1997007777A1 (fr) * 1995-08-15 1997-03-06 Robert Eric Montgomery Compositions orales activant la peroxydase
DE19710068A1 (de) * 1997-03-12 1998-09-17 Kramer Axel Mittel zur Förderung der Mundhygiene und der Mundgesundheit

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6264924B1 (en) * 1998-02-27 2001-07-24 The Procter & Gamble Company Oral care compositions comprising chlorite and methods
WO2003000216A1 (fr) * 2001-06-23 2003-01-03 Lg Household & Health Care Ltd. Pastilles multicouches pour blanchiment dentaire
GB2402621A (en) * 2003-06-09 2004-12-15 Sharron Marsden Lollipop/sweet for dental hygiene purposes
WO2006002287A1 (fr) * 2004-06-23 2006-01-05 Hofmann Robert F Utilisation de preparation therapeutique oxydative ciblee dans un traitement endodontique
US11211249B2 (en) 2008-03-06 2021-12-28 Sensient Flavors Llc Herbal extracts and flavor systems for oral products and methods of making the same
CH707698A1 (de) * 2013-03-12 2014-09-15 Bonyf Ag Pharmazeutisches Mittel zur Behandlung von Schleimhautentzündungen.
EP2777708A1 (fr) 2013-03-12 2014-09-17 Bonyf AG Produit pharmaceutique, notamment pour le traitement d'inflammations de la muqueuse
US10543230B2 (en) 2013-10-07 2020-01-28 Rdg Holding, Inc. Redox signaling gel formulation
CH710357A1 (de) * 2014-11-11 2016-05-13 Bogaert Jean-Pierre Kosmetisches und pharmazeutisches Mittel zur Behandlung von Hautrissen.
EP3218069B1 (fr) * 2014-11-11 2025-01-29 Jean-Pierre Bogaert Agent cosmétique et pharmaceutique pour traiter des plaies et/ou des hémorragies cutanées, muqueuses ou gingivales, notamment p. ex. des fissures de la peau (rhagades) ou une parodontite
WO2016075169A1 (fr) * 2014-11-11 2016-05-19 Jean-Pierre Bogaert Agent cosmétique et pharmaceutique pour traiter des plaies et/ou des hémorragies cutanées, muqueuses ou gingivales, notamment p. ex. des fissures de la peau (rhagades) ou une parodontite
US12318404B2 (en) 2016-01-19 2025-06-03 Reoxcyn LLC Hypochlorite formulations for wound healing
US10485827B2 (en) 2016-01-19 2019-11-26 Rdg Holdings, Inc. Topical eye serum compositions, methods or preparing, and methods of use
US11083689B2 (en) 2016-05-18 2021-08-10 Reoxcyn, Llc Lubricant formulations
US10471003B2 (en) 2016-05-18 2019-11-12 Reoxcyn, Llc Lubricant formulations
US11857674B2 (en) 2016-05-18 2024-01-02 Reoxcyn, Llc Lubricant formulations
US11376278B2 (en) 2016-08-11 2022-07-05 Sulfilatec, Inc. Compositions and methods for treating disease
WO2018031922A1 (fr) * 2016-08-11 2018-02-15 Sulfilatec, Inc. Compositions médicales et nutritionnelles et méthodes d'utilisation
US9833471B1 (en) 2016-09-15 2017-12-05 Reoxcyn Discoveries Group, Inc. Hypochlorous acid-based hand sanitizer
WO2018122529A1 (fr) * 2016-12-28 2018-07-05 Bochenek Stephane Gel de blanchiment dentaire sur base naturelle et sans peroxydes
EP3342394A1 (fr) * 2016-12-28 2018-07-04 Stephane Bochenek Gel de blanchiment dentaire sur base naturelle et sans peroxydes
US11583481B2 (en) 2017-01-16 2023-02-21 Reoxcyn, Llc Dentifrice formulations and methods of oral care

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