WO1992018091A1 - Compositions antimicrobiennes orales - Google Patents

Compositions antimicrobiennes orales Download PDF

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Publication number
WO1992018091A1
WO1992018091A1 PCT/US1992/002359 US9202359W WO9218091A1 WO 1992018091 A1 WO1992018091 A1 WO 1992018091A1 US 9202359 W US9202359 W US 9202359W WO 9218091 A1 WO9218091 A1 WO 9218091A1
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WO
WIPO (PCT)
Prior art keywords
oral
acid
oral composition
thymol
monoperphthalic
Prior art date
Application number
PCT/US1992/002359
Other languages
English (en)
Inventor
Michael Frederick Lukacovic
Satyanarayana Majeti
David Allen Weber
Original Assignee
The Procter & Gamble Company
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 The Procter & Gamble Company filed Critical The Procter & Gamble Company
Publication of WO1992018091A1 publication Critical patent/WO1992018091A1/fr

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Classifications

    • 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
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • 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
    • A61K8/34—Alcohols
    • A61K8/347—Phenols
    • 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

  • Bacteria and yeast are a part of the normal flora of the skin. They also exist prevalently on all mucous membrane surfaces as indigenous flora. Given the proper circumstances and opportunity to penetrate tissues, bacteria from the indigenous flora can set up infections, such as gas gangrene, vulvovaginal abscess, 1 chronic sinusitis, and
  • Monoperoxy acids are known for treating microbial diseases of the oral cavity.
  • U.S. Patent 4,990,329, issued February 5, 1991 to Sampathku ar discloses an oral hygiene composition comprising a monoperphthalic acid compound or its pharmaceutically-acceptable salts or esters. These compositions are used to treat or prevent anaerobic infections in humans and lower animals.
  • U.S. Patent 4,886,658, issued December 12, 1989 to Charbonneau discloses methods for treating or preventing dental plaque, caries, or gingival or periodontal diseases of the oral cavity in humans or lower animals, with reduced staining of teeth or dentures.
  • Compositions suitable for use in this invention comprise a monoperoxyphthalate compound and an anti-plaque bis-biguanide compound.
  • U.S. Patent 4,716,035, issued December 29, 1987 to Sampath- kumar discloses oral compositions comprising certain organic peroxy acid agents and a source of fluoride ions. These .compo ⁇ sitions are used as anticaries and antigingivitis agents.
  • Monoperoxy acids are also used for other disinfecting/ cleansing purposes.
  • U.S. Patent 4, 917,815, issued April 17, 1990 to Beil fuss et a! . discloses aqueous solutions of aromatic percarboxyl ic acids. Uses for this invention include acidic or neutral l iquid disin ⁇ fectants for surfaces with l ow to medium l oading of di rt for the skin, the mucous membranes or the hands .
  • U.S. Patent 4,490, 269 i ssued December 25, 1984 to Gallopo discloses a denture cl eansing composition compri sing an efferves ⁇ cent agent, and as a bleaching agent, a monoperphthal ate or a potassium monopersulfate and a monoperphthal ate.
  • Percarboxyl ic acids which may be empl oyed in this invention incl udes monoperphthal ic acid.
  • U.S. Patent 3,988,433, i ssued October 26, 1976 to Benedict discloses compositions containing al kyl and aryl peroxy acids . These compositions are stated to be useful to remove stains from teeth.
  • Thymol a phenolic compound useful in the present invention, is known to have some antibacterial properties.
  • Listerine® antiseptic mouthrinse sold by Warner-Lambert Company is a thymol- containing product currently on the market.
  • the present invention provides oral compositions useful for treating or preventing microbial infection of the oral cavity, said oral compositions comprising: (a) from about 0.25% to about 5% of a monoperphthalic acid compound; and (b) from about 0.025% to about 0.1% thymol.
  • the present invention further relates to methods of treating or preventing microbial infections of the oral cavity, such methods comprising administering to a human or lower animal in need of such treatment, and possibly exhibiting an overgrowth of yeast, an oral composition comprising a monoperphthalic acid and thymol as described hereinafter.
  • the present invention relates to compositions and methods for treating or preventing microbial diseases of the oral cavity by administering to humans or lower animals a composition comprising a safe and effective amount of a monoperphthalic acid and thymol.
  • diseases of the oral cavity is meant diseases which are initiated and/or perpetuated by bacteria in the oral cavity, and includes such diseases as, for example, perio- dontal disease, gingivitis, periodontitis, gingivosis, perio- dontosis, periodontitis complex, and other inflammatory and/or degenerative conditions of the tissues within the oral cavity, plus caries, Vincent's disease, trench mouth, malodor, and yeast overgrowth.
  • dentoalveolar infectious, 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
  • Noma i.e., gangrenous stomatitis or cancrum oris
  • Oral and dental infections are more fully disclosed in Fingold, 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 incorporated herein by reference.
  • the method of treatment of the present invention is particularly effective for treating or preventing periodontal disease, gingivitis and/or periodontitis, while lessening the potential for an overgrowth of yeast to occur in the oral cavity.
  • safety and effective amount as used herein is meant an amount of a monoperphthalic acid compound, or its pharmaceuti- cally-acceptable salt or ester, high enough to significantly positively modify the infection to be treated, but low enough to avoid serious side effects (at a reasonable benefit/risk ratio), within the scope of sound medical judgment.
  • a monoperphthalic acid compound or its pharmaceutically-acceptable salt or ester will vary with the particular infection (e.g., disease of the oral cavity) being treated, the age and physical condition of the patient being treated, the severity of the infection, the duration of treatment, the nature of concurrent therapy, the specific form (i.e., acid, salt, and/or ester) of the monoperphthalic acid employed, and the particular vehicle from which the monoperphthalic acid is applied.
  • the monoperphthalic acid compounds, useful in this invention are substituted monoperphthalic acids having the general structure:
  • R may be one or more substituents compatible with the peroxy acid functionality of the aromatic ring.
  • substituted and unsubstituted saturated alky are substituted and unsubstituted saturated alky!
  • esters and salts of the substituted or unsub ⁇ stituted monoperphthalic acid compounds which have the same general antibacterial properties as the preferred magnesium salt of monoperphthalic acid, and which are acceptable from a toxicity viewpoint.
  • 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 compounds for treating or preventing diseases of the oral cavity are pharmaceutically-acceptable salts of the substituted or unsub ⁇ stituted monoperphthalic acid compounds, with the pharmaceu- tically-acceptable salts of divalent cations more preferred (e.g., magnesium, calcium) and the magnesium salt being the most preferred.
  • magnesium salt of monoperphthalic acid is the magnesium salt of monoperphthalic acid.
  • This magnesium salt is the salt of the carboxylic acid group only, having the formula:
  • Synthesis of substituted and unsubstituted monoperphthalic acid compounds can be achieved by those skilled in the art using methods disclosed in, for example, European Patent Application No. 27,693, published Apr. 29, 1981, filed by Interox Chemicals Limited; European Patent Application 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 being incorporated herein by reference. Synthesis of the magnesium salt of monoperphthalic acid is disclosed in the European Patent Application No. 27,693, cited above.
  • the amount of monoperphthalic acid or its pharmaceutically-acceptable salts or esters is from about 0.01% to about 55%; a more preferred amount is from about 0.25% to about 22.1%.
  • the most preferred amount of monoperphthalic acid or its pharmaceutically-acceptable salts or esters useful in the present invention is from about 0.5% to about 17.7%.
  • Thymol Thymol is a phenolic compound necessary in the oral compo ⁇ sitions of the present invention to extend the antimicrobial spectrum of the monoperphthalic acid to include yeast. Thymol aids in reducing viable yeast in the oral cavity, thereby decreasing the potential for an overgrowth of yeast to occur when a patient is undergoing treatment with the use of a monoper ⁇ phthalic acid composition.
  • Thymol is obtained from the essential oil of the plants Thymus vulgaris L. and Monarada punctata L., Labiatae. Thymol is a phenolic compound having the general structure: CH 3
  • thymol has use for destroying mold and herbarium parasites. Thymol has been recommended for the prevention of mildew growth.
  • Merck Tenth Edition, Number 9246, page 1347, published in 1983 by Merck & Co., Inc., incorporated herein by reference in its entirety. Thymol is available commercially from Sigma Chemical Company, St. Louis, Missouri.
  • the amount of thymol present in the oral compositions of the present invention is from about 0.01% to about 12.37%; more preferably from about 0.025% to about 6.19%; and most preferably from about 0.05% to about 2.65%.
  • Suitable Carripr Materials are examples of thymol present in the oral compositions of the present invention.
  • Suitable carrier materials for the oral compositions of the present invention are preferably in the form of any of a number of conventional oral care products, for example, a solution (e.g., mouthrinse, a dentifrice (e.g., toothpaste, gel or tooth powder), chewing gum, chewable tablets, lozenge or sachet.
  • a solution e.g., mouthrinse, a dentifrice (e.g., toothpaste, gel or tooth powder), chewing gum, chewable tablets, lozenge or sachet.
  • Preferred compositions useful in the methods of the present invention are solutions and dentifrices
  • suitable carrier materials should be compatible with the monoperphthalic acid and thymol present in the oral co po- sitions of the present invention.
  • compatible is meant that the components of the composition are capable of being commingled without interaction in a manner which would substantially reduce the compositions efficacy for treating or preventing microbial diseases of the oral cavity, according to the method of the present invention.
  • sweetening agents e.g. saccharin, aspartame, magnasweet
  • coloring agents e.g. saccharin, aspartame, magnasweet
  • humectants emulsifying agents
  • buffering agents e.g., aqueous carriers
  • suitable aqueous carriers means water or a mixture of water and any alcohol that is proven to be safe for human use.
  • a buffering agent is useful in the present invention to maintain a desirable pH of the monoperphthalic acid/thymol containing compositions of from about 5 to about 7, and preferably from about 5 to about 5.5.
  • suitable buffering agents for the present invention include sodium bicarbonate, citric acid, malic acid, tartaric acid, gluconic acid and monosodium phosphate.
  • Preferred buffering agents for the present invention are sodium bicarbonate, citric acid, and monosodium phosphate.
  • the oral compositions of the present invention may contain a water-soluble fluoride compound in an amount sufficient to give a fluoride concentration of from about 0.0025% to about 5.0% by weight, preferably from about 0.005% to about 2.0% by weight, to provide anticaries effectiveness.
  • the fluoride compounds are believed to provide protection against deminerali- zation as well as aid in re ineralization of dental enamel.
  • Preferred fluorides are sodium fluoride, stannous fluoride, indium fluoride, and sodium onofluorophosphate.
  • Norris et a!., U.S. Patent 2,946,725, issued July 26, 1960 and Widder et al., U.S. Patent 3,678,154, issued July 18, 1972 disclose such salts as well as others.
  • the pharmaceutically-acceptable carrier materials in the oral monoperphthalic acid/thymol-containing compositions of the present invention are present in a range of from about 32.63% to about
  • the preferred dentifrice compositions useful in the methods of the present invention for treating or preventing microbial infections, including overgrowth of yeast, in the oral cavity comprise a monoperphthalic acid or its pharmaceutically-acceptable salts or esters in an amount of from about 0.01% to about 10%; more preferably from about 1.0% to about 7.5%; most preferably from about 2.5% to about 5%; thymol in an amount of from about 0.025% to about 1.5%; more preferably from about 0.25% to about 1.25%; most preferably from about 0.25% to about 1.0%; and suitable carrier materials in an amount of from about 88.5% to about 99.97%; more preferably from about 91.25% to about 98.75%; most preferably from about 94% to about 97.25%.
  • compositions useful in the methods of the present invention are in the form of granules which may then be dissolved in a suitable aqueous carrier for use as a mouthrinse or mouth spray.
  • Granular compositions useful in the methods of the present invention comprise a monoperphthalic acid or its pharmaceutically-acceptable salts or esters in an amount of from about 1.76% to about 55%; more preferably from about 4.4% to about 22.1%; most preferably from about 8.8% to about 17.7%; and thymol in an amount of from about 0.17% to about 12.37%; more preferably from about 0.44% to about 6.19%; most preferably from about 0.88% to about 2.65%; and suitable carrier materials .in an amount of from about 32.63% to about 98.07%; more preferably from about 71.71% to about 95.16%; most preferably from about 79.65% to about 90.32%.
  • the method of this invention to treat or prevent microbial diseases of the oral cavity comprising administering to humans or lower animals in need of such treatment or prevention an oral composition comprising a monoperphthalic acid compound and thymol as described in detail hereinabove.
  • such oral compo- sitions are preferably used from about once to about four times, more preferably once or twice daily, most preferably twice daily.
  • the methods of the present invention comprise contacting such monoperphthalic acid/thymol-containing compositions with the dental surfaces in the oral cavity for from about one second to about 300 seconds during each use, more preferably for from about 10 seconds to about 120 seconds, during each use, and most preferably for from about 30 seconds to about 60 seconds during each use.
  • granule compositions useful in the methods of the present invention may be used in preparing aqueous compositions that may then be used to treat or prevent microbial infections of the oral cavity, including an overgrowth of yeast, in humans or lower animals in need of such treatment.
  • the aqueous solution of monoperphthalic acid or its pharmaceutically-acceptable salts or esters and thymol are prepared by dissolving the granule compositions, as described in detail hereinabove, in a suitable aqueous carrier such that the resulting solutions provide monoperphthalic acid or its pharmaceutically-acceptable salts or esters in a range of from about 0.1% to about 5%; more preferably from about 0.25% to about 1.25%; most preferably from about 0.5% to about 1%; and thymol in a range of fro * -, about 0.0» to about 0.7%; more preferably from about 0.025* to about 0.35%; most preferably from about 0.05% to about 0.15%. .
  • These monoperphthalic acid/thymol-containing solut i ons are used in the methods of the present invention to treat or prevent microbial infections, of the oral cavity, including an overgrowth of yeast, said methods comprising having a human or lower an i mal in need of such treatment swish or otherwise retain and move around in the oral cavity from about 5 ml to about 30 ml; more preferably from about 10 ml to about 20 ml ; most preferably from about 12 ml to about 18 ml of said solutions.
  • the monoperphthalic acid/thymol containing dentifrice compo ⁇ sitions are used in the methods of the present invention to treat or prevent microbial infections in the oral cavity, including an overgrowth of yeast, said methods comprising having a human or lower animal in need of such treatment brush their teeth or have their teeth brushed with preferably 0.2gms to about 2.5gms; more preferably O. ⁇ gms to about 2.0gms; most preferably lgm to about l. ⁇ gms of said dentifrice compositions.
  • PAM Dentifrice is a combination product consisting of 90% aqueous phase and 10% nonaqueous phase.
  • a )SASS is a 28% aqueous solution of sodium alkyl sulfate, sold by Sigma Chemical Company, St. Louis, Missouri.
  • Example II A mouthrinse solution is made by dissolving the following components in water and mixing.
  • the composition of the mouthrinse is as follows:
  • a human or lower animal in need of a method of treatment or prevention of microbial diseases of the oral cavity swishes the above mouthrinse composition around the oral cavity twice daily for 30 to 60 seconds during each use.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Birds (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Cosmetics (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Cette invention concerne des compositions et leur utilisation dans des procédés de traitement et/ou de prévention des infections microbiennes dans la cavité buccale chez l'homme et/ou d'autres animaux inférieurs nécessitant un traitement de cet ordre. Lesdites compositions sont constituées d'un composé d'acide monoperphtalique et de thymol.
PCT/US1992/002359 1991-04-19 1992-03-25 Compositions antimicrobiennes orales WO1992018091A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US68873491A 1991-04-19 1991-04-19
US688,734 1991-04-19

Publications (1)

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WO1992018091A1 true WO1992018091A1 (fr) 1992-10-29

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PCT/US1992/002359 WO1992018091A1 (fr) 1991-04-19 1992-03-25 Compositions antimicrobiennes orales

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WO (1) WO1992018091A1 (fr)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19508827A1 (de) * 1995-03-11 1996-09-12 Bode Chemie Gmbh & Co Wund- und Schleimhautantiseptikum
WO1997026855A1 (fr) * 1996-01-24 1997-07-31 Warner-Lambert Company Compositions pour bains de bouche contenant des huiles essentielles et du peroxyde et systemes en deux parties pour bain de bouche
WO1998010738A1 (fr) * 1996-09-16 1998-03-19 The Procter & Gamble Company Compositions de soins buccaux antimicrobienne
WO1998054279A1 (fr) * 1997-05-30 1998-12-03 The Procter & Gamble Company Compositions desinfectantes et procedes de desinfection de surfaces
US6103683A (en) * 1996-01-12 2000-08-15 The Procter & Gamble Co. Disinfecting compositions and processes for disinfecting surfaces
WO2011151171A1 (fr) * 2010-05-31 2011-12-08 Unilever Nv Composition pour le traitement de la peau
US8945596B2 (en) 2008-10-20 2015-02-03 Conopco, Inc. Antimicrobial composition
US9132103B2 (en) 2009-09-24 2015-09-15 Conopco, Inc. Disinfecting agent comprising eugenol, terpineol and thymol
US9408870B2 (en) 2010-12-07 2016-08-09 Conopco, Inc. Oral care composition
US9693941B2 (en) 2011-11-03 2017-07-04 Conopco, Inc. Liquid personal wash composition

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4925655A (en) * 1988-03-04 1990-05-15 Robell Research Powder composition for forming a mouthwash
EP0373429A2 (fr) * 1988-12-14 1990-06-20 The Procter & Gamble Company Méthode de traitement buccal pour réduire la formation de la plaque dentaire avec une faible coloration des dents

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4925655A (en) * 1988-03-04 1990-05-15 Robell Research Powder composition for forming a mouthwash
EP0373429A2 (fr) * 1988-12-14 1990-06-20 The Procter & Gamble Company Méthode de traitement buccal pour réduire la formation de la plaque dentaire avec une faible coloration des dents

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19508827A1 (de) * 1995-03-11 1996-09-12 Bode Chemie Gmbh & Co Wund- und Schleimhautantiseptikum
US6103683A (en) * 1996-01-12 2000-08-15 The Procter & Gamble Co. Disinfecting compositions and processes for disinfecting surfaces
WO1997026855A1 (fr) * 1996-01-24 1997-07-31 Warner-Lambert Company Compositions pour bains de bouche contenant des huiles essentielles et du peroxyde et systemes en deux parties pour bain de bouche
WO1998010738A1 (fr) * 1996-09-16 1998-03-19 The Procter & Gamble Company Compositions de soins buccaux antimicrobienne
WO1998054279A1 (fr) * 1997-05-30 1998-12-03 The Procter & Gamble Company Compositions desinfectantes et procedes de desinfection de surfaces
US8945596B2 (en) 2008-10-20 2015-02-03 Conopco, Inc. Antimicrobial composition
US9132103B2 (en) 2009-09-24 2015-09-15 Conopco, Inc. Disinfecting agent comprising eugenol, terpineol and thymol
WO2011151171A1 (fr) * 2010-05-31 2011-12-08 Unilever Nv Composition pour le traitement de la peau
CN102905683A (zh) * 2010-05-31 2013-01-30 荷兰联合利华有限公司 皮肤处理组合物
CN102905683B (zh) * 2010-05-31 2015-09-23 荷兰联合利华有限公司 皮肤处理组合物
US9408870B2 (en) 2010-12-07 2016-08-09 Conopco, Inc. Oral care composition
US9693941B2 (en) 2011-11-03 2017-07-04 Conopco, Inc. Liquid personal wash composition

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