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Flavour blend for masking unpleasant taste of zinc compounds

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Publication number
WO2000028952A1
WO2000028952A1 PCT/GB1999/003779 GB9903779W WO2000028952A1 WO 2000028952 A1 WO2000028952 A1 WO 2000028952A1 GB 9903779 W GB9903779 W GB 9903779W WO 2000028952 A1 WO2000028952 A1 WO 2000028952A1
Authority
WO
Grant status
Application
Patent type
Prior art keywords
zinc
flavouring
taste
oil
administered
Prior art date
Application number
PCT/GB1999/003779
Other languages
French (fr)
Inventor
Essat Bilali
Original Assignee
Block Drug Company, Inc.
Whalley, Kevin
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

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Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/30Cosmetics or similar toilet preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34Alcohols
    • A61K8/342Alcohols having more than seven atoms in an unbroken chain
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/19Cosmetics or similar toilet preparations characterised by the composition containing inorganic ingredients
    • A61K8/20Halogens; Compounds thereof
    • A61K8/21Fluorides; Derivatives thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/19Cosmetics or similar toilet preparations characterised by the composition containing inorganic ingredients
    • A61K8/27Zinc; Compounds thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/92Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/922Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILET PREPARATIONS
    • A61Q11/00Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59Mixtures
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S514/00Drug, bio-affecting and body treating compositions
    • Y10S514/849Cough and cold preparation

Abstract

A synergistic flavouring combination of at least a flavouring oil and lauryl alcohol for use in an orally administered formulation which contains an ionisable zinc compound having an undesirable taste. The flavouring combination is unexpectedly effective in masking the unpleasant taste or aftertaste of zinc.

Description

Flavour Blend For Masking Unpleasant Taste Of Zinc Compounds

BACKGROUND OF THE INVENTION

1. Field of Invention. This invention relates to a flavouring method and flavour composition for masking flavour and taste of compositions for oral absorption and administration by humans which contain zinc compounds.

2. General background. The value of the element zinc is well-established. Zinc has a vital role in a number of pharmaceutical formulations. Zinc deficiency is an important feature of many cases of sickle cell anaemia characterised by growth retardation and hypogonadism, and zinc appears to have an antisickling effect. Zinc has also been shown to be beneficial in the relief of acute inflammatory conditions associated with rheumatoid arthritis. Use of zinc gluconate and zinc acetate has been described as a method for reducing duration of common cold symptoms. Zinc oxides are used in a number of dental products such as dentifrices, denture adhesives, dental fillings, dental cements, and dental impression materials. Zinc salts are generally reported to enhance activity of triclosan and cationic anti-microbials in dentifrices and mouthwashes. Zinc chloride has been recognised as possessing anti-odour properties in oral health care products. Zinc citrates are useful in reducing dental calculus formation.

In recent years, formulations for oral administration and /or absorption such as tablets, powders, lozenges, syrups, sprays, dentifrices, mouthwashes, etc. have been formulated containing a zinc component. One of the major drawbacks of the incorporation of zinc compounds into various orally absorbed or administered products has been the characteristic bitterness of zinc that is experienced as soon as the zinc compound is released and proceeds to break down in the mouth. A variety of formulations and methods have been prepared and attempted to lessen or mask entirely the bitter taste and aftertaste of zinc compounds.

US Pat. Nos. 4,684,528 and 4,758,439 disclose the formulation of zinc compounds with glycine and certain other amino acids to reduce the unpalatable and undesirable aftertaste of prior zinc formulations. US Patent No. 5,095,035 teaches masking compositions which contain zinc acetate with the addition of extramolar citric acid. US Patent No. 5,002,970 discloses that ionisable zinc compounds can be masked with anethole to eliminate or reduce the taste and after taste of zinc. US Patent No. 5,766,622 teaches the use of phosphorylated amino acid in oral compositions to inhibit bitter and/or metallic taste from a pharmaceutical active component. US Patent No. 5,817,295 discloses a tripartite blend of peppermint oils that provides for a pleasant tasting mouthwash and masking the bitter taste of essential oils used for antimicrobial efficacy in the mouthwash.

There is still a need for a new way to eliminate the objectionable taste and after taste of zinc compounds using new technologies.

SUMMARY OF THE INVENTION

The present invention relates to an orally administered formulation comprising about 0.1 to 25 wt. % of an ionisable zinc compound having an undesirable taste, and a synergistic flavouring combination of at least a flavouring oil and lauryl alcohol in an amount effective to mask the undesirable taste of said ionisable zinc compound.

The invention also provides a method for improving the taste of an orally administered formulation containing about 0.1 to 25 wt. % of an ionisable zinc compound with undesirable taste, by mixing into said formulation a synergistic flavouring combination of at least a flavouring oil and lauryl alcohol in an amount effective to mask the undesirable taste of said ionisable zinc.

DESCRIPTION OF THE INVENTION The present invention provides an orally administered formulation containing an ionisable zinc compound with undesirable taste, but without the unpleasant metallic taste of zinc. The formulation can be in the form of foods, pharmaceuticals, toiletries, etc. The formulation contains an ionisable zinc compound and a carrier medium making up the balance.

Zinc Compounds. The orally administered formulations may contain one or more ionisable zinc compounds depending on the application. Zinc compounds include both inorganic and organic zinc salts and, in particular, salts such as the halides, nitrates, sulfates, chromates, silicates, and compounds comprising complexes of these materials constituting the inorganic salts contemplated herein. Organic salts of zinc include but not limited zinc gluconate, zinc formate, zinc succinate, zinc aspartate and the like. Particular zinc halides include zinc chloride, zinc bromide, zinc fluoride, and mixtures.

In terms of specific applications, typical zinc compounds used in dental formulations include such materials as zinc oxide for use in inhibiting bacterial attack in dentifrices. Zinc oxide is also used as a binding materials in denture adhesives. Zinc chloride and zinc citrate are used as anti-odour ingredients in dental formulations. Zinc acetate and hydroxide is used for their anti-plaque properties. Zinc citrate, polyphosphates such as disodium ethane- 1- hydroxy-1, 1-diphosphonate (EHDP), pyrophosphate, tetrametaphosphate, metaphosphate and orthophosphate salts of zinc for tartar removal effects in dentifrices. Zinc glycerophosphate, zinc phenolsulfonate, zinc fluorosilicate, zinc fluorozirconate are known for their astringent and deodorant capabilities. Zinc citrate is preferred for dental formulations. Zinc acetate and zinc gluconate are favoured in compositions for treating common colds.

In general, the concentration of zinc compounds in orally administered formulations varies from about 0.1 to 15 wt. %. The concentration can range up to as much as 25% depending on the particular formulation in which the zinc compound is incorporated. A more preferred amount is about 0.2 to 2 wt. %. A most preferred amount is from about 0.5 to 2 wt. %.

Flavouring / masking components: The taste masking / flavouring combination of the present invention is made up of a mixture of flavouring oils and lauryl alcohol.

For the purpose of this invention, flavouring oils used herein refer to both entire essential oils and the aroma chemicals making up the essential oils. Essential oils are predominately volatile materials from botanical sources. The most widely used process for the isolation of essential oils is steam distillation of plant matter, although dry distillation and solvent extraction are also used. Essential oils are generally recognised as safe compositions that can be included in ingested materials. Aroma chemicals refer to chemicals which may be synthetic or natural, derived from essential oils, i.e., derived from plants by distillation, expression, or extraction, and which usually carry the flavour of the plant from which they are derived.

Although the invention is not limited to the specific essential oils listed individually in this specification, a number of important essential oils include spearmint oil; peppermint oil; wintergreen oil; lavender oil; sassafras oil; ginger oil; clove oil; sage oil; basil oil; eucalyptus oil; laurel oil; mayonara oil; cinnamon oil; camomile oil; thyme oil; citrus oils such as lemon oil, orange oil, grapefruit oil, tangerine oil; oil of anise; camphor oil; and the like.

Aroma chemicals include but not limited to anethole, carvone, cintronellal, camphor, linalool, menthol, menthone, thymol, and the like.

It has been found that in an orally administered formulation of the claimed invention, the additional presence of lauryl alcohol in combination with a mixture of flavouring oils as a flavouring composition, enhances the organoleptic properties, imparts freshness in the mouth and masks the unpleasant taste and aftertaste of the zinc compound in the formulation. The flavouring oils appear to be operating in synergistic combination, perhaps with the lauryl alcohol or perhaps because of the ability of various components of the flavouring oils themselves to inhibit different biological pathways associated with bioavailability.

The individual flavouring oils can be mixed and matched as desired to provide the intended flavour in the orally administered composition. The concentrations of the individual components can therefore vary quite widely. It is preferred, nevertheless, that the flavouring oils in total will be about 80 - 99.5 wt. % of the synergistic taste masking / flavouring combination, and most preferred about 95 - 99%. The lauryl alcohol makes up the rest of the masking / flavouring combination.

In general, the synergistic taste masking / flavouring combination is present in an amount of about 0.1 to 5 wt. % of the orally administered formulation. A preferred amount is about 0.1-3% wt. %. A most preferred amount is from about 0.1 to 2 wt. %.

Carriers & Other Ingredients: The carriers vary according to the applications. In toothpastes it is desirable to employ thickening agents such as hydroxyethylcellulose and water-soluble salts of cellulose ethers, including sodium carboxymethyl cellulose and sodium carboxymethylhydroxyethyl cellulose; or natural gums, including gum karaya, gum arabic, and gum tragacanth. Also, colloidal magnesium aluminium silicate or finely divided silica can be used as part of the thickening agent to improve the texture of the product. Thickening agents are used at levels of from 0.1 % to 5.0%> of the toothpaste composition. It is also desirable to include a humectant material in toothpastes. Suitable materials for this purpose include glycerine, sorbitol, and other edible polyhydric alcohols or mixtures thereof. These materials can comprise from about 1%> to about 50% of the toothpaste composition. Dentifrices normally also contain sweetening agents. Suitable sweetening agents for use in dentifrices include for example saccharin, dextrose and levulose. The sweetening agents are used at levels of from about 0.05% to about 2%. In addition to the aforementioned typical components of a toothpaste, water usually comprises the balance of the toothpaste, and is usually present at levels up to about 50%.

Mouthwashes generally comprise a water/ethyl alcohol solution and optionally other ingredients such as sweeteners, and humectants such as those mentioned above for dentifrices. The alcohols provide an antibacterial effect and help the solubility of the flavouring oils. Optionally, mouthwashes also contain sudsing agents. Humectants such as glycerine and sorbitol give a moist and sweet feel in the mouth and are desirably also present. While these materials are not always essential, they are useful to help solubilise and enhance the flavouring oils, and aid in making the product sweet, smoother and imparting body. Antibacterial agents are sometimes incorporated into mouthwashes or dentifrices at levels from about 0.01% to about 2.0%. Generally, mouthwashes suitable for use as carriers herein contain: 5% to 40% ethyl alcohol; 0% to 20%, preferably 5% to 20%, glycerine or other humectant; 0% to 12%, preferably 0.1% to 12%, sudsing agent, 0% to 0.5%, preferably 0.05% to 0.5%), sweetening agent such as saccharin; and 0%> to 0.3%, preferably 0.05%> to 2% of the flavouring / masking components of the present invention; and the balance, water with colorants or dyes if desired.

Chewing gum suitable for use as a carrier herein comprises a gum base and flavouring materials such as those mentioned above for dentifrices. The flavouring materials are present at a level of 0.01 % to about 2.0% of the final chewing gum composition. The gum base is a chewable plastic gum material such as natural rubber, chicle, polyvinyl acetate, ester gum, coumarone resin, and paraffin wax. The gum base is typically made from a mixture of two or more plastic gum materials to achieve a preferred degree of plasticity for chewing. Optionally, corn syrup is added as a softener and binder for the chewing gum and sugar is optionally added as a sweetener and adding nuance to the flavour. A typical chewing gum suitable as a carrier herein comprises 15%> to 30% gum base, 15% to 20% corn syrup, 50% to 65% sugar, 1% of zinc gluconate trihydrate, and 0.05%) to 1.5% of the flavouring / masking composition of the invention.

Lozenges suitable as carriers herein comprise a hard sugar candy base and one or more flavouring oils. Optionally, lozenges can contain various other materials. A typical lozenge suitable as a carrier in this invention is a hard candy comprised of a hard candy base containing 0.05% to 1.5 wt. % of the flavouring / masking components and about 1 wt. % of zinc acetate dihydrate. The hard candy base is a solidified solution of amorphous sugar which is generally formed from a sugar solution which has been cooked at high temperature so as to remove nearly all of the moisture. The taste masking / flavouring materials are added before the moisture is removed.

The orally administered compositions of the present invention can also optionally contain additional therapeutic materials including for example, water-soluble fluoride such as sodium fluoride and stannous fluoride.

Preparations: The orally administered compositions of the present invention without the metallic zinc taste can be prepared by any convenient method. The individual components of the synergistic masking / flavouring composition can be added separately as separate components to the orally administered compositions, but it is generally preferred to prepare the masking / flavouring composition separately and thereafter combine it with the orally administered compositions.

The orally administered compositions of the present invention can be in solid forms such as tablets, lozenges and powders; chewable forms such as chewing gums and soft candies; paste and gel forms such as dentifrices; liquids such as syrups, mouthwashes, and sprays. Flavoured lozenges with zinc compounds can be prepared by mixing the masking components of the present invention with the carriers and other ingredients, then by direct compression of the ingredients.

When the compositions are applied to or in contact with oral and oral pharyngeal membranes of a human, they are palatable and without undesirable taste or unpleasant metallic taste of zinc compounds. The flavours produced are truer, smoother, and better in taste than formulations without the masking/flavouring components of the present invention. In order to further illustrate the present invention, examples are set forth below. All parts and percentages are by weight and all temperatures in degrees in centigrade unless otherwise indicated.

Various flavouring compositions were prepared by mixing the components (in wt. %) set forth in Table 1 that follows: TABLE 1

The flavour compositions were combined into a dentifrice composition containing the following components, shown in Table 2 below: TABLE 2

In blind taste tests, it is found that the dentifrice compositions containing the masking / flavouring compositions in the Examples exhibit "good tasting" properties and without any trace of the unpleasant metallic taste of zinc compounds.

Various changes and modifications can be made in the products of the present invention without departing from the spirit and scope thereof. The various embodiments which were disclosed herein were for the purpose of further illustrating the invention but were not intended to limit it.

Claims

CLAIMS:
1. An orally administered formulation that releases zinc ions to the oral and oral pharyngeal mucous membranes of a human comprising a suitable carrier and uniformly contained in said formulation: about 0.1 to 25 wt. % of an ionisable zinc compound having an undesirable taste; a synergistic flavouring combination of at least a flavouring oil and lauryl alcohol in an amount effective to mask the undesirable taste of said ionisable zinc compound.
2. The orally administered formulation of claim 1, wherein the lauryl alcohol is present in an amount of about 0.5-20 wt. % of the synergistic flavouring combination.
3. The orally administered formulation of claim 1 or claim 2, wherein said at least a flavouring oil is selected from the group consisting of: peppermint oil, spearmint oil, carvone, anethole and mixtures thereof.
4. The orally administered formulation of any one of claims 1 to 3, wherein said ionisable zinc compound is selected from the group consisting of: zinc oxide, zinc citrate, zinc chloride, zinc acetate, zinc hydroxide, zinc fluorosilicate, zinc fluorozirconate , zinc acetate, zinc gluconate and mixtures thereof.
5. The orally administered formulation of claim 4, wherein said ionisable zinc compound is zinc citrate.
6. The orally administered formulation of any one of claims 1 to 5, in the form of a dentifrice.
7. The orally administered formulation of any one of claims 1 to 5, in the form of a lozenge.
8. The orally administered formulation of any one of claims 1 to 5, in the form of a mouth rinse.
9. The orally administered formulation of any one of claims 1 to 5, in the form of a chewable tablet.
10. The orally administered formulation of any one of claims 1 to 5, in the form of a syrup.
11. The orally administered formulation of any one of claims 1 to 5, selected from the group consisting of foods, pharmaceuticals, and mixtures thereof.
12. A method for improving the taste of an orally administered formulation, which formulation includes about 0.1 to 25 wt. % of an ionisable zinc compound having an undesirable taste, said method comprising mixing a synergistic flavouring combination of at least a flavouring oil and lauryl alcohol in an amount effective to mask the undesirable taste of said ionisable zinc.
13. The method of claim 12, wherein the lauryl alcohol is present in an amount of about 0.5-20 wt. % of the synergistic flavouring combination.
14. The method of claim 12 or claim 13, wherein said flavouring oil is selected from the group consisting of: peppermint oil, spearmint oil, carvone, anethole and mixtures thereof.
15. The method of any one of claims 12 to 14, wherein said ionisable zinc compound is selected from the group consisting of: zinc oxide, zinc citrate, zinc chloride, zinc acetate, zinc hydroxide, zinc fluorosilicate, zinc fluorozirconate, zinc acetate, zinc gluconate and mixtures thereof.
16. The method of any one of claims 12 to 15, wherein said orally administered formulation is selected from the group consisting of foods, pharmaceuticals, and mixtures thereof.
17. A preformulation consisting essentially of about 80 - 99.5 wt. % of at least a flavouring oil and about 0.5 to 20 wt. % lauryl alcohol, wherein said preformulation when uniformly mixed in an orally administered formulation containing about 0.1 to 25 wt. % of an ionisable zinc compound with undesirable taste, masks the undesirable taste of said ionisable zinc compound.
18. The preformulation of claim 17, wherein said flavouring oil is selected from the group consisting of: peppermint oil, spearmint oil, carvone, anethole and mixtures thereof.
19. The preformulation of claim 17 or claim 18, wherein said orally administered formulation is selected from the group consisting of foods, pharmaceuticals, and mixtures thereof.
20. The preformulation of any one of claims 17 to 19, wherein said ionisable zinc compound is selected from the group consisting of: zinc oxide, zinc citrate, zinc chloride, zinc acetate, zinc hydroxide, zinc fluorosilicate, zinc fluorozirconate , zinc acetate, zinc gluconate and mixtures thereof.
PCT/GB1999/003779 1998-11-12 1999-11-12 Flavour blend for masking unpleasant taste of zinc compounds WO2000028952A1 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
US10821298 true 1998-11-12 1998-11-12
US60/108,212 1998-11-12
US09434334 US6169118B1 (en) 1998-11-12 1999-11-04 Flavor blend for masking unpleasant taste of zinc compounds
US09/434,334 1999-11-04

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP19990954239 EP1128800A1 (en) 1998-11-12 1999-11-12 Flavour blend for masking unpleasant taste of zinc compounds
JP2000582000A JP2002529489A (en) 1998-11-12 1999-11-12 Flavor blend in order to hide the unpleasant taste of zinc compounds
CA 2350450 CA2350450A1 (en) 1998-11-12 1999-11-12 Flavour blend for masking unpleasant taste of zinc compounds

Publications (1)

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WO2000028952A1 true true WO2000028952A1 (en) 2000-05-25

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US (1) US6169118B1 (en)
JP (1) JP2002529489A (en)
CN (1) CN1333674A (en)
CA (1) CA2350450A1 (en)
EP (1) EP1128800A1 (en)
RU (1) RU2241436C2 (en)
WO (1) WO2000028952A1 (en)

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* Cited by examiner, † Cited by third party
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US8778311B2 (en) 2006-03-22 2014-07-15 The Procter & Gamble Company Oral zinc compositions
US9371317B2 (en) 2013-02-19 2016-06-21 Senomyx, Inc. Sweet flavor modifier
US9382196B2 (en) 2008-07-31 2016-07-05 Senomyx, Inc. Processes and intermediates for making sweet taste enhancers
US9420814B2 (en) 2012-08-06 2016-08-23 Senomyx, Inc. Sweet flavor modifier
US9603848B2 (en) 2007-06-08 2017-03-28 Senomyx, Inc. Modulation of chemosensory receptors and ligands associated therewith
US9775792B2 (en) 2012-12-19 2017-10-03 Colgate-Palmolive Company Oral care products comprising a tetrabasic zinc-amino acid-halide complex

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6641801B1 (en) * 2000-04-03 2003-11-04 Love Lives Gargle method to reduce the duration of common cold symptoms
WO2003017962A1 (en) * 2001-08-24 2003-03-06 Unilever N.V. Oral composition comprising an alkylhydroxybenzoate
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EP1458386B1 (en) * 2001-12-27 2007-04-18 Ortho-McNeil Pharmaceutical, Inc. Aroyl pyrrole heteroeryl and methanols useful for treating a central nervous system disorder
US7247328B2 (en) * 2002-05-31 2007-07-24 Zinpro Corporation Chromium (III) alpha amino acid complexes
US7129375B2 (en) * 2002-10-16 2006-10-31 Zinpro Corporation Metal complexes of α amino dicarboxylic acids
WO2004050664A1 (en) * 2002-12-05 2004-06-17 Md Bioalpha Co., Ltd. Method for preparation of amino acid chelate
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WO2004098566A3 (en) * 2003-04-30 2004-12-23 Tim Clarot Chewable lozenge cold remedy composition and method for making same
WO2004098571A1 (en) * 2003-04-30 2004-11-18 Zicam, Llc Cold remedy composition comprising zinc salts
WO2005092277A1 (en) * 2004-03-25 2005-10-06 Unilever N.V. Oral composition
WO2006135445A3 (en) * 2004-11-03 2007-10-04 Albion Lab Antimicrobial chelates
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US20090226549A1 (en) * 2008-03-06 2009-09-10 Kenneth John Hughes Herbal extracts and flavor systems for oral products and methods of making the same
US20100189663A1 (en) * 2009-01-24 2010-07-29 Gallis Karl W Mouth rinse compositions including chemically modified silica or silicate materials for sustained delivery to tooth surfaces
US20110206749A1 (en) * 2010-02-19 2011-08-25 J.M. Huber Corporation Silica materials for reducing oral malador
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US20110236444A1 (en) * 2010-03-25 2011-09-29 Darsillo Michael S Antimicrobial Silica Composites
US9486396B2 (en) * 2010-12-21 2016-11-08 Colgate-Palmolive Company Metal salt compositions
RU2452464C1 (en) * 2011-01-14 2012-06-10 Людмила Адамовна Экпеньонг Therapeutic tooth paste
WO2014098824A1 (en) * 2012-12-19 2014-06-26 Colgate-Palmolive Company Oral gel comprising zinc - amino acid complex
KR20150095701A (en) * 2012-12-19 2015-08-21 콜게이트-파아므올리브캄파니 Oral care compositions comprising zinc amino acid halides
CA2937763A1 (en) * 2014-02-27 2015-09-03 The Procter & Gamble Company Compositions with reduced bitter taste perception

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1055854A (en) * 1964-05-22 1967-01-18 Hoffmann La Roche Water-dispersible veterinary preparations and a process for their manufacture
EP0049671A1 (en) * 1980-10-07 1982-04-14 BioSystems Research, Inc. New metal oxyalkylates, pharmaceutical compositions containing the same and process for preparing the same
JPS59101418A (en) * 1982-12-02 1984-06-12 Lion Corp Composition for oral cavity
JPS6366115A (en) * 1986-09-09 1988-03-24 Lion Corp Composition for oral cavity for deodorizing nicotine
US4758439A (en) * 1984-06-11 1988-07-19 Godfrey Science & Design, Inc. Flavor of zinc supplements for oral use
US5002970A (en) * 1981-07-31 1991-03-26 Eby Iii George A Flavor masked ionizable zinc compositions for oral absorption

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5095035A (en) 1981-07-31 1992-03-10 Eby Iii George A Flavor stable zinc acetate compositions for oral absorption
GB2179536B (en) 1984-06-11 1988-12-21 Godfrey Science & Design Inc Improvement in the flavour of zinc supplements for oral use
CA2143037C (en) 1994-05-02 2002-04-30 Atma Chaudhari Alcohol free mouthwash
US5700449A (en) * 1994-10-18 1997-12-23 Kao Corporation Dentifrice composition
US5766622A (en) 1996-08-14 1998-06-16 The Procter & Gamble Company Inhibiting undesirable taste in oral compositions

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1055854A (en) * 1964-05-22 1967-01-18 Hoffmann La Roche Water-dispersible veterinary preparations and a process for their manufacture
EP0049671A1 (en) * 1980-10-07 1982-04-14 BioSystems Research, Inc. New metal oxyalkylates, pharmaceutical compositions containing the same and process for preparing the same
US5002970A (en) * 1981-07-31 1991-03-26 Eby Iii George A Flavor masked ionizable zinc compositions for oral absorption
JPS59101418A (en) * 1982-12-02 1984-06-12 Lion Corp Composition for oral cavity
US4758439A (en) * 1984-06-11 1988-07-19 Godfrey Science & Design, Inc. Flavor of zinc supplements for oral use
JPS6366115A (en) * 1986-09-09 1988-03-24 Lion Corp Composition for oral cavity for deodorizing nicotine

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
PATENT ABSTRACTS OF JAPAN vol. 008, no. 218 (C - 245) 4 October 1984 (1984-10-04) *
PATENT ABSTRACTS OF JAPAN vol. 012, no. 297 (C - 519) 12 August 1988 (1988-08-12) *

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8778311B2 (en) 2006-03-22 2014-07-15 The Procter & Gamble Company Oral zinc compositions
US9603848B2 (en) 2007-06-08 2017-03-28 Senomyx, Inc. Modulation of chemosensory receptors and ligands associated therewith
US9732052B2 (en) 2008-07-31 2017-08-15 Senomyx, Inc. Processes and intermediates for making sweet taste enhancers
US9382196B2 (en) 2008-07-31 2016-07-05 Senomyx, Inc. Processes and intermediates for making sweet taste enhancers
CN103354758A (en) * 2011-02-15 2013-10-16 高露洁-棕榄公司 Taste -masked oral care compositions
RU2574026C2 (en) * 2011-02-15 2016-01-27 Колгейт-Палмолив Компани Composition for oral care with corrected taste
CN103354758B (en) * 2011-02-15 2016-04-20 高露洁-棕榄公司 Taste-masked oral care compositions
WO2012112141A1 (en) * 2011-02-15 2012-08-23 Colgate-Palmolive Company Taste -masked oral care compositions
US9420814B2 (en) 2012-08-06 2016-08-23 Senomyx, Inc. Sweet flavor modifier
US9745293B2 (en) 2012-08-06 2017-08-29 Senomyx, Inc. Sweet flavor modifier
US9687015B2 (en) 2012-08-06 2017-06-27 Senomyx, Inc. Sweet flavor modifier
US9775792B2 (en) 2012-12-19 2017-10-03 Colgate-Palmolive Company Oral care products comprising a tetrabasic zinc-amino acid-halide complex
US9695162B2 (en) 2013-02-19 2017-07-04 Senomyx, Inc. Sweet flavor modifier
US9475803B2 (en) 2013-02-19 2016-10-25 Senomyx, Inc. Sweet flavor modifier
US9371317B2 (en) 2013-02-19 2016-06-21 Senomyx, Inc. Sweet flavor modifier

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JP2002529489A (en) 2002-09-10 application
US6169118B1 (en) 2001-01-02 grant
EP1128800A1 (en) 2001-09-05 application
CN1333674A (en) 2002-01-30 application
RU2241436C2 (en) 2004-12-10 grant
CA2350450A1 (en) 2000-05-25 application

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