WO1995001173A1 - Amphoteric surfactant for the treatment of aphthous ulcers - Google Patents

Amphoteric surfactant for the treatment of aphthous ulcers Download PDF

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Publication number
WO1995001173A1
WO1995001173A1 PCT/EP1994/002130 EP9402130W WO9501173A1 WO 1995001173 A1 WO1995001173 A1 WO 1995001173A1 EP 9402130 W EP9402130 W EP 9402130W WO 9501173 A1 WO9501173 A1 WO 9501173A1
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WO
WIPO (PCT)
Prior art keywords
amphoteric surfactant
composition
use according
aphthous ulcers
oral
Prior art date
Application number
PCT/EP1994/002130
Other languages
French (fr)
Inventor
Franciscus Johnannes G. Van Der Ouderaa
Diane Cummins
Kevin Hammond
Michael David Traudt
Original Assignee
Unilever N.V.
Unilever Plc
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 Unilever N.V., Unilever Plc filed Critical Unilever N.V.
Priority to EP94919671A priority Critical patent/EP0706389A1/en
Priority to AU70736/94A priority patent/AU7073694A/en
Publication of WO1995001173A1 publication Critical patent/WO1995001173A1/en

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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
    • A61K31/13—Amines
    • 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
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • 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
    • A61K31/205—Amine addition salts of organic acids; Inner quaternary ammonium salts, e.g. betaine, carnitine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K33/00—Medicinal preparations containing inorganic active ingredients
    • A61K33/24—Heavy metals; Compounds thereof
    • A61K33/30—Zinc; Compounds thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof

Definitions

  • Amphoteric surfactant for the treatment of aphthous ulcers is amphoteric surfactant for the treatment of aphthous ulcers.
  • the present invention relates to the prevention, inhibition and/or reduction of minor recurrent aphthous stomatitis by the use of an oral composition which comprises an amphoteric surfactant.
  • Aphthous stomatitis is a general term describing a disease affecting the mucous membrane in the mouth, causing the formation of small, whitish ulcers, called aphthae or more commonly aphthous ulcers. These aphthous ulcers cause severe discomfort to the patient as they are rather painful and irritating.
  • aphthae small, whitish ulcers
  • Several treatments for aphthous ulcers have already been proposed, e.g. gargle compositions with an astringent material or with cellulosealkylethers or with homocarnosine, but none of these treatments have found wide usage as effective anti- aphthae treatments.
  • amphoteric surfactants have a considerable anti- aphthae activity, significantly preventing, inhibiting and/or reducing the formation of aphthous ulcers in the mouth.
  • the present invention relates to the use of an amphoteric surfactant in the manufacture of an oral composition for preventing, inhibiting and/or reducing aphthous ulcers.
  • Amphoteric surfactants are well-known per se. They are surfactants of which the hydrophilic group has both acid and alkaline properties, depending upon the pH of the medium in which they are present. In acid media they form cations, and in alkaline media anions. In the isoelectric pH range they are present in the form of zwitterions. It is preferred in the present invention that the amphoteric surfactant is present in a cationic or zwitterionic form in the oral composition.
  • Amphoteric surfactants have been described extensively in the prior art, and reference is made to Schwartz, Perry and Berch, Synthetic Detergents and Surfactants, Vol. I and II for further details which are hereby incorporated by way of reference. Typical examples can be represented by the following general formula:
  • R is a fatty alkyl or acyl residue, which may be interrupted by heteroatoms
  • R 2 and R 3 are hydrogen or short alkyl residues
  • R contains one or more methylene units
  • Y is an acid residue.
  • Typical examples are the alkylglycinates, alkylproprionates, betaines, sulphobetaines, phosphatobetaines, as well as tertiary amine oxides which, although not amphoteric in structure, behave like amphoteric surfactants.
  • fatty acidamidoalkyl betaines such as l-alcoylamino-3-dimethylammonio-propane- 3-carboxy methyl betaine, in which the alcoyl group contains from 7-17 carbon atoms.
  • This product is commercially available from Th. Goldschmidt AG, Germany under the name Tego® Betain BL 281.
  • amphoteric surfactant is used in the present invention in an amount of 0.01-6%, usually 0.1-3% and preferably 0.25-2% by weight.
  • the amphoteric surfactant-containing composition of the present invention can be manufactured in any form, suitable for orally administering the composition to achieve the prevention, inhibition and/or reduction of aphthous ulcers.
  • Such forms are tablets, capsules, pills, powders, granules, solutions, gargles, suspensions, salves, gels, pastes etc.
  • the composiion is an oral composition.
  • Particularly suitable forms of the oral composition are toothpastes, mouthwashes, gels and the like.
  • Oral compositions in gel form are particularly preferred in the present invention.
  • the oral composition may furthermore comprise conventional ingredients, such as pharmaceutically acceptable carriers like starch, sucrose, polyols, surfactants, water or water/alcohol systems etc.
  • pharmaceutically acceptable carriers like starch, sucrose, polyols, surfactants, water or water/alcohol systems etc.
  • such formulation may contain all the usual dentifrice ingredients.
  • they may comprise particulate abrasive materials such as silicas, aluminas, calcium carbonates, dicalciumphosphates, hydroxyapatites, trimetaphosphates, insoluble hexa etaphosphates and so on, usually in amounts between 5 and 60% by weight.
  • the dentifrice formulations may comprise humectants such as glycerol, sorbitol, propyleneglycol, lactitol and so on.
  • additional surface-active agents may also be included such as anionic, nonionic and zwitterionic synthetic detergents.
  • anionic, nonionic and zwitterionic synthetic detergents examples thereof are sodiumlaurylsulphate, sodium dodecylbenzenesulphonate, sodium mono- and dioctyl-phosphate, sodiumlauroylsarcosinate, alkyleneoxide condensation products with fatty alcohols, with fatty acid esters, block copoly ers of ethylene oxide and propyleneoxide.
  • Nonionic surface-active agents are preferred as additional surfactant when an additional surfactant is included.
  • Binders and thickeners such as sodium carboxymethyl- cellulose, xanthan gum, gum arabic etc. may also be included, as well as synthetic polymers such as polyacrylates and carboxyvinyl polymers such as Carbopol®.
  • Flavours such as peppermint and spearmint oils may also be included, as well as preservatives, opacifying agents, colouring agents, pH-adjusting agents, sweetening agents and so on.
  • Anti-bacterial agents may also be included such as chlorhexidine, copper-, zinc- and stannous salts such as zinc citrate and stannous pyrophosphate, sanguinarine extract, metronidazole. Further examples of anti-bacterial agents are quaternary ammonium compounds such as cetylpyridinium chloride; bis-guanides such as chlorhexidine digluconate, hexetidine, octenidine, alexidine; halogenated bisphenolic compounds such as 2,2' methylenebis-(4-chloro-6-bromophenol) .
  • a preferred anti- bacterial agent is Triclosan (2 1 ,4 ,4 * -trichloro-2-hydroxy- diphenylether) .
  • the amount of Triclosan used in the present invention may vary from 0.0001 - 5% by weight, preferably from 0.01 - 3% by weight and particularly preferably from 0.1 - 2% by weight of the oral composition.
  • Polymeric compounds which can enhance the delivery of active ingredients such as the anti-bacterial agents can also be included.
  • examples of such polymers are copolymers of polyvinylmethylether with maleic anhydride and other similar delivery enhancing polymers, e.g. those described in DE-A-3,942,643 (Colgate)
  • anti-inflammatory agents such as ibuprofen, flurbiprofen, aspirin, indo ethacin etc. may also be included.
  • Anti-caries agents such as sodium- and stannous fluoride, aminefluorides, monosodiumfluorophosphate, calcium lactate and/or calcium glycerophosphates, strontium salts and strontium polyacrylates, casein and casein digests and phosphoproteins may also be included.
  • vitamins such as Vitamin C, plant extracts, potassium salts such as potassium citrate, potassium chloride and potassium nitrate.
  • enzymes such as dextranase and/or mutanase, amyloglucosidase, glucose- oxida ⁇ e with lactoperoxidase, neuraminidases, and hydrogenperoxide generating compounds such as potassiu peroxydiphosphate.
  • the oral compositions may comprise anti- calculus agents such as alkalimetalpyrophosphates, hypophosphite-containing polymers, organic phosphonates, phosphocitrates etc..
  • anti- calculus agents such as alkalimetalpyrophosphates, hypophosphite-containing polymers, organic phosphonates, phosphocitrates etc.
  • bacteriocins e.g. bacteriocins, bacteriophages, tissue respiratory factors, antibodies, bleaching agents such as peroxy compounds, effervescing systems such as sodiumbicarbonate/citric acid systems, colour change systems, and so on.
  • bleaching agents such as peroxy compounds
  • effervescing systems such as sodiumbicarbonate/citric acid systems, colour change systems, and so on.
  • Preferred amphoteric surfactant-containing compositions for use in the present invention contain Triclosan, either alone or together with a zinc salt such as zinc citrate.
  • a zinc salt such as zinc citrate.
  • the amount of zinc salt used in such combination ranges from 0.01 - 5% by weight of the composition, preferably from 0.1 - 3% by weight of the composition.
  • Other suitable zinc salts are those, disclosed in US-A-4, 022 ,880, as well as alkalimetal zinc citrates such as sodium zinc citrate.
  • amphoteric surfactant-containing compositions which contain Triclosan and a copolymer of polyvinylmethylether with maleic anhydride or another delivery-enhancing polymer as described in DE-A-3 ,942 , 643.
  • the amount of such polymer may vary from 0.005-4% by weight of the composition.
  • a zinc salt may also be present in these polymer-containing compositions, such as zinc citrate or zinc glycinate in the above specified amounts.
  • Example 1 The invention will further be illustrated by the following Examples: Example 1
  • Titanium dioxide 1.00
  • compositions contained either no surfactant at all (A) , or 1.9 % cocamidoprop ' yl betaine (B) or 1.5 % sodium laurylsulphate (C) .
  • Toothpaste B 0.64 % CAPB 1.27 % CAPB 1.90 % CAPB with
  • Toothpaste C 0.5 % SLS 1.0 % SLS 1.5 % SLS with

Abstract

The present invention relates to the use of an amphoteric surfactant in the manufacture of a composition for the prevention, inhibition and/or reduction of aphthous ulcers. Preferably, the compositions are oral compositions such as toothpastes and mouthwashes. The oral composition is especially preferably in a gel form. Preferably the amphoteric surfactant is a betaine, particularly a fatty acidamidoalkylbetaine.

Description

Amphoteric surfactant for the treatment of aphthous ulcers.
The present invention relates to the prevention, inhibition and/or reduction of minor recurrent aphthous stomatitis by the use of an oral composition which comprises an amphoteric surfactant.
Aphthous stomatitis is a general term describing a disease affecting the mucous membrane in the mouth, causing the formation of small, whitish ulcers, called aphthae or more commonly aphthous ulcers. These aphthous ulcers cause severe discomfort to the patient as they are rather painful and irritating. Several treatments for aphthous ulcers have already been proposed, e.g. gargle compositions with an astringent material or with cellulosealkylethers or with homocarnosine, but none of these treatments have found wide usage as effective anti- aphthae treatments.
We have now found that amphoteric surfactants have a considerable anti- aphthae activity, significantly preventing, inhibiting and/or reducing the formation of aphthous ulcers in the mouth.
Consequently, the present invention relates to the use of an amphoteric surfactant in the manufacture of an oral composition for preventing, inhibiting and/or reducing aphthous ulcers.
Amphoteric surfactants are well-known per se. They are surfactants of which the hydrophilic group has both acid and alkaline properties, depending upon the pH of the medium in which they are present. In acid media they form cations, and in alkaline media anions. In the isoelectric pH range they are present in the form of zwitterions. It is preferred in the present invention that the amphoteric surfactant is present in a cationic or zwitterionic form in the oral composition.
Amphoteric surfactants have been described extensively in the prior art, and reference is made to Schwartz, Perry and Berch, Synthetic Detergents and Surfactants, Vol. I and II for further details which are hereby incorporated by way of reference. Typical examples can be represented by the following general formula:
R,(R,) (R3)N*-R4-Y*,
in which R, is a fatty alkyl or acyl residue, which may be interrupted by heteroatoms, R2 and R3 are hydrogen or short alkyl residues, R contains one or more methylene units and Y is an acid residue. Many varieties exist, and the aforementioned reference contains numerous examples of amphoteric surfactants.
Typical examples are the alkylglycinates, alkylproprionates, betaines, sulphobetaines, phosphatobetaines, as well as tertiary amine oxides which, although not amphoteric in structure, behave like amphoteric surfactants.
Specific examples are:
sodium cocoamphoacetate disodium cocoamphodiacetate sodium carboxy ethyl oleic polypropylamine sodium cocoamphoproprionate disodium cocoamphodiproprionate lauryl betaine cocamidopropyl betaine tallow dihydroxyethyl betaine coco sultaine coca idopropyl hydroxysultaine lauryl dimethyl amine oxide n-alkyl ethoxy dimethyl amine oxide
Particularly preferred are the fatty acidamidoalkyl betaines such as l-alcoylamino-3-dimethylammonio-propane- 3-carboxy methyl betaine, in which the alcoyl group contains from 7-17 carbon atoms. This product is commercially available from Th. Goldschmidt AG, Germany under the name Tego® Betain BL 281.
The amphoteric surfactant is used in the present invention in an amount of 0.01-6%, usually 0.1-3% and preferably 0.25-2% by weight.
The amphoteric surfactant-containing composition of the present invention can be manufactured in any form, suitable for orally administering the composition to achieve the prevention, inhibition and/or reduction of aphthous ulcers. Such forms are tablets, capsules, pills, powders, granules, solutions, gargles, suspensions, salves, gels, pastes etc. Preferably, the composiion is an oral composition. Particularly suitable forms of the oral composition are toothpastes, mouthwashes, gels and the like. Also it is possible to formulate the oral composition in forms, suitable for buccal administration, such as irrigator fluids, chewing gum, lozenges, and adhesive strips. Oral compositions in gel form are particularly preferred in the present invention.
The oral composition may furthermore comprise conventional ingredients, such as pharmaceutically acceptable carriers like starch, sucrose, polyols, surfactants, water or water/alcohol systems etc. When formulated into a dentifrice, such formulation may contain all the usual dentifrice ingredients. Thus, they may comprise particulate abrasive materials such as silicas, aluminas, calcium carbonates, dicalciumphosphates, hydroxyapatites, trimetaphosphates, insoluble hexa etaphosphates and so on, usually in amounts between 5 and 60% by weight.
Furthermore, the dentifrice formulations may comprise humectants such as glycerol, sorbitol, propyleneglycol, lactitol and so on.
Minor amounts of additional surface-active agents may also be included such as anionic, nonionic and zwitterionic synthetic detergents. Examples thereof are sodiumlaurylsulphate, sodium dodecylbenzenesulphonate, sodium mono- and dioctyl-phosphate, sodiumlauroylsarcosinate, alkyleneoxide condensation products with fatty alcohols, with fatty acid esters, block copoly ers of ethylene oxide and propyleneoxide. Nonionic surface-active agents are preferred as additional surfactant when an additional surfactant is included.
Binders and thickeners such as sodium carboxymethyl- cellulose, xanthan gum, gum arabic etc. may also be included, as well as synthetic polymers such as polyacrylates and carboxyvinyl polymers such as Carbopol®.
Flavours such as peppermint and spearmint oils may also be included, as well as preservatives, opacifying agents, colouring agents, pH-adjusting agents, sweetening agents and so on.
Anti-bacterial agents may also be included such as chlorhexidine, copper-, zinc- and stannous salts such as zinc citrate and stannous pyrophosphate, sanguinarine extract, metronidazole. Further examples of anti-bacterial agents are quaternary ammonium compounds such as cetylpyridinium chloride; bis-guanides such as chlorhexidine digluconate, hexetidine, octenidine, alexidine; halogenated bisphenolic compounds such as 2,2' methylenebis-(4-chloro-6-bromophenol) . A preferred anti- bacterial agent is Triclosan (21,4 ,4*-trichloro-2-hydroxy- diphenylether) . The amount of Triclosan used in the present invention may vary from 0.0001 - 5% by weight, preferably from 0.01 - 3% by weight and particularly preferably from 0.1 - 2% by weight of the oral composition.
Polymeric compounds which can enhance the delivery of active ingredients such as the anti-bacterial agents can also be included. Examples of such polymers are copolymers of polyvinylmethylether with maleic anhydride and other similar delivery enhancing polymers, e.g. those described in DE-A-3,942,643 (Colgate)
Furthermore anti-inflammatory agents such as ibuprofen, flurbiprofen, aspirin, indo ethacin etc. may also be included.
Anti-caries agents such as sodium- and stannous fluoride, aminefluorides, monosodiumfluorophosphate, calcium lactate and/or calcium glycerophosphates, strontium salts and strontium polyacrylates, casein and casein digests and phosphoproteins may also be included.
Other optional ingredients include vitamins such as Vitamin C, plant extracts, potassium salts such as potassium citrate, potassium chloride and potassium nitrate.
Other optional ingredients include enzymes such as dextranase and/or mutanase, amyloglucosidase, glucose- oxidaεe with lactoperoxidase, neuraminidases, and hydrogenperoxide generating compounds such as potassiu peroxydiphosphate.
Furthermore, the oral compositions may comprise anti- calculus agents such as alkalimetalpyrophosphates, hypophosphite-containing polymers, organic phosphonates, phosphocitrates etc..
Other optional ingredients that may be included are e.g. bacteriocins, bacteriophages, tissue respiratory factors, antibodies, bleaching agents such as peroxy compounds, effervescing systems such as sodiumbicarbonate/citric acid systems, colour change systems, and so on.
Preferred amphoteric surfactant-containing compositions for use in the present invention contain Triclosan, either alone or together with a zinc salt such as zinc citrate. The amount of zinc salt used in such combination ranges from 0.01 - 5% by weight of the composition, preferably from 0.1 - 3% by weight of the composition. Other suitable zinc salts are those, disclosed in US-A-4, 022 ,880, as well as alkalimetal zinc citrates such as sodium zinc citrate.
Also preferred for use in the present invention are amphoteric surfactant-containing compositions which contain Triclosan and a copolymer of polyvinylmethylether with maleic anhydride or another delivery-enhancing polymer as described in DE-A-3 ,942 , 643. The amount of such polymer may vary from 0.005-4% by weight of the composition. A zinc salt may also be present in these polymer-containing compositions, such as zinc citrate or zinc glycinate in the above specified amounts.
The invention will further be illustrated by the following Examples: Example 1
The following toothpaste formulations were tested as to their effect on the incidence of aphthous ulcers:
wt %
Sorbitol, 70 % syrup 45.00
Abrasive silica 10.00
Thickening silica 10.00
Xanthan gum 1.00
Saccharin 0.20
Titanium dioxide 1.00
Sodium monofluorophosphate 0.80
Flavour 1.00
Polyethylene glycol 5.00
Surfactant X
Water q.s
The compositions contained either no surfactant at all (A) , or 1.9 % cocamidoprop'yl betaine (B) or 1.5 % sodium laurylsulphate (C) .
Patients suffering from recurrent aphthous ulceration were treated with the formulations using the following method: patients brushed with the test and placebo formulations for identical periods of time, and the numbers of new ulcers formed over each period were compared. Products were tested sequentially, with each patient using each product during the test. The test involved 25 patients, and the following results were obtained:
Toothpaste A B C
Mean number 7.36 ± 1.3 9.16 ± 1.2 13.12 ± 1.7 of ulcers ± SEM
Example 2
The effect on abnormal desquamation (or sloughing) of the toothpastes with varying amounts of cocamidopropyl betain (CAPB) (B) or sodium laurylsulphate (SLS) (C) was determined, in a study involving 28 patients using a cap- splint. A custom-made cap-splint containing the test toothpaste was placed over the attached gingiva lining the upper dentition (2 min./appln., bid, 4 days) . The affected gingiva was then examined for any sloughing caused by the toothpaste treatment.
The following results were obtained:
Toothpaste B 0.64 % CAPB 1.27 % CAPB 1.90 % CAPB with
Total number 1 1 1 of patients with oral desquamation
Toothpaste C 0.5 % SLS 1.0 % SLS 1.5 % SLS with
Total number 9 16 17 of patents with oral desquamation

Claims

Cla ims
1. Use of an amphoteric surfactant in the manufacture of a composition for the prevention, inhibition and/or reduction of aphthous ulcers.
2. Use according to claim 1, characterised in that the amphoteric surfactant is a betaine.
3. Use according to claim 2, characterised in that the amphoteric surfactant is a fatty acidamidoalkylbetaine.
4. Use according to claim 1, characterised in that the composition is an oral composition.
5. Use according to claim 4, characterised in that the oral composition is a dentifrice or a mouthwash.
6. Use according to claim 4, characterised in that the oral composition is in a gel form.
7. Use according to claims 1-6 characterised in that the composition furthermore comprises Triclosan.
8. Use according to claims 1-7, characterised in that the composition furthermore comprises a zinc salt.
9. Use according to claim 7, characterised in that the composition furthermore comprises a polymer which enhances the delivery of the Triclosan.
PCT/EP1994/002130 1993-07-01 1994-06-29 Amphoteric surfactant for the treatment of aphthous ulcers WO1995001173A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP94919671A EP0706389A1 (en) 1993-07-01 1994-06-29 Amphoteric surfactant for the treatment of aphthous ulcers
AU70736/94A AU7073694A (en) 1993-07-01 1994-06-29 Amphoteric surfactant for the treatment of aphthous ulcers

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP93305154 1993-07-01
EP93305154.2 1993-07-01

Publications (1)

Publication Number Publication Date
WO1995001173A1 true WO1995001173A1 (en) 1995-01-12

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0692246A1 (en) * 1994-07-15 1996-01-17 Colgate-Palmolive Company Oral compositions
US5681548A (en) * 1994-07-15 1997-10-28 Colgate Palmolive Company Oral formulations
WO2005092277A1 (en) * 2004-03-25 2005-10-06 Unilever N.V. Oral composition

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4287174A (en) * 1978-03-31 1981-09-01 The Proctor & Gamble Company Anti-ulcer composition
JPH021402A (en) * 1988-03-18 1990-01-05 Sunstar Inc Dentifrice composition
EP0408174A1 (en) * 1989-07-12 1991-01-16 Warner-Lambert Company Antiseptic composition containing hexahydro-5-pyrimidinamine compounds

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4287174A (en) * 1978-03-31 1981-09-01 The Proctor & Gamble Company Anti-ulcer composition
JPH021402A (en) * 1988-03-18 1990-01-05 Sunstar Inc Dentifrice composition
EP0408174A1 (en) * 1989-07-12 1991-01-16 Warner-Lambert Company Antiseptic composition containing hexahydro-5-pyrimidinamine compounds

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* Cited by examiner, † Cited by third party
Title
J.E.F. REYNOLDS: "MARTINDALE THE EXTRA PHARMACOPOEIA", 1982, THE PHARMACEUTICAL PRESS, LONDON *
O. DONATSKY ET AL.: "IN VITRO DEMONSTRATION OF CELLULAR HYPERSENSITIVITY TO STREP 2A IN RECURRENT APHTHOUS STOMATITIS BY MEANS OF THE LEUCOCYTE MIGRATION TEST", ACTA ALLERGOLOGICA, vol. 27, no. 2, 1972, pages 137 - 144 *
PATENT ABSTRACTS OF JAPAN vol. 14, no. 126 (C - 0699) 9 March 1990 (1990-03-09) *
R.A. LINDEMANN ET AL.: "SERUM ANTIBODY RESPONSES TO INDIGENOUS ORAL MUCOSAL ANTIGENS AND SELECTED LABORATORY-MAINTAINED BACTERIA IN RECURRENT APHTHOUS ULCERATION", ORAL SURGERY ORAL MEDICINE ORAL PATHOLOGY, vol. 59, no. 6, 1985, pages 585 - 589 *
STN FILE SUPPLIER; MEDLINE: AN=87093909 *
WANG SW ET AL.: "THE TRACE ELEMENT ZINC AND APHTHOSIS", REV. STOMATOL. CHIR. MAXILLOFAC., vol. 87, no. 5, 1986, pages 339 - 343 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0692246A1 (en) * 1994-07-15 1996-01-17 Colgate-Palmolive Company Oral compositions
US5681548A (en) * 1994-07-15 1997-10-28 Colgate Palmolive Company Oral formulations
WO2005092277A1 (en) * 2004-03-25 2005-10-06 Unilever N.V. Oral composition

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Publication number Publication date
EP0706389A1 (en) 1996-04-17
AU7073694A (en) 1995-01-24

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