DE2212148A1 - Effective mixtures against tooth decay - Google Patents

Effective mixtures against tooth decay

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Publication number
DE2212148A1
DE2212148A1 DE19722212148 DE2212148A DE2212148A1 DE 2212148 A1 DE2212148 A1 DE 2212148A1 DE 19722212148 DE19722212148 DE 19722212148 DE 2212148 A DE2212148 A DE 2212148A DE 2212148 A1 DE2212148 A1 DE 2212148A1
Authority
DE
Germany
Prior art keywords
sodium
lysine
compounds
dextran
active
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
DE19722212148
Other languages
German (de)
Inventor
Gerhard Julius Woodcliff Lake N.J. Haas (V.StA.). C 12k 1-04
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
General Foods Corp
Original Assignee
General Foods Corp
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
Priority claimed from US05/148,203 external-priority patent/US3932603A/en
Application filed by General Foods Corp filed Critical General Foods Corp
Publication of DE2212148A1 publication Critical patent/DE2212148A1/en
Pending legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G3/00—Sweetmeats; Confectionery; Marzipan; Coated or filled products
    • A23G3/34—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof
    • A23G3/36—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof characterised by the composition containing organic or inorganic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G3/00—Sweetmeats; Confectionery; Marzipan; Coated or filled products
    • A23G3/34—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof
    • A23G3/36—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof characterised by the composition containing organic or inorganic compounds
    • A23G3/362—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof characterised by the composition containing organic or inorganic compounds containing inorganic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G3/00—Sweetmeats; Confectionery; Marzipan; Coated or filled products
    • A23G3/34—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof
    • A23G3/36—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof characterised by the composition containing organic or inorganic compounds
    • A23G3/364—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof characterised by the composition containing organic or inorganic compounds containing microorganisms or enzymes; containing paramedical or dietetical agents, e.g. vitamins
    • A23G3/366—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof characterised by the composition containing organic or inorganic compounds containing microorganisms or enzymes; containing paramedical or dietetical agents, e.g. vitamins containing microorganisms, enzymes
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G4/00—Chewing gum
    • A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G4/00—Chewing gum
    • A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds
    • A23G4/064—Chewing gum characterised by the composition containing organic or inorganic compounds containing inorganic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G4/00—Chewing gum
    • A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds
    • A23G4/14—Chewing gum characterised by the composition containing organic or inorganic compounds containing peptides or proteins
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/24—Phosphorous; Compounds thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • 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
    • 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
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
    • 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
    • A61K8/64—Proteins; Peptides; Derivatives or degradation products 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
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783—Angiosperms [Magnoliophyta]
    • A61K8/9789—Magnoliopsida [dicotyledons]
    • 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
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783—Angiosperms [Magnoliophyta]
    • A61K8/9794—Liliopsida [monocotyledons]
    • 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
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/42—Colour properties
    • A61K2800/43—Pigments; Dyes

Description

PATENTANWÄLTEPATENT LAWYERS

DR.-iNG. VON KREISLER DR.-ING. SCHÖNWÄLD 22 1 2 1 48 DR.-ING. TH. MEYER DR. FUES DIPL-CHEM. AlEK VON KREJSLER DlPL-CHEM. CAROLA KELLER DR.-ING. KLÖPSCH DIPL-ING. SELTINGDR.-iNG. BY KREISLER DR.-ING. SCHÖNWÄLD 22 1 2 1 48 DR.-ING. TH. MEYER DR. FUES DIPL-CHEM. AlEK BY KREJSLER DlPL-CHEM. CAROLA KELLER DR.-ING. KLÖPSCH DIPL-ING. SELTING

5 KÖLN 1, DEICHMANNHAUS5 COLOGNE 1, DEICHMANNHAUS

Köln, den 10,3.1972 Fu/Ax/HzCologne, March 10th, 1972 Fu / Ax / Hz

GENERAL FOODS CORPORATION, GENERA L FOODS CORPORATION,

250 North Street, White. Plains, New York (U.S.A*).250 North Street, White. Plains, New York (U.S.A *).

Wirksame Gemische gegen Kariesbefall. Effective mixtures against tooth decay.

Die Zahnkaries hat vielfältige Ursachen. Eine dieser Ursachen ist bei den Mikroorganismen zu suchen. Damit Zahnkaries sich entwickeln kann, muß eine Infektion durch Mikroorganismen stattfinden.Dental caries has a variety of causes. One of these causes can be found in the microorganisms. In order to Tooth caries can develop, an infection by microorganisms must take place.

In den letzten Jahren wurde festgestellt, daß die Mikroorganismen, die am häufigsten mit der Bildung von vielflächiger Karies im Zusammenhang stehen, gewisse salivare Streptokokken sind, die zur Gruppe Streptococcus mutans gehören. Diese vielflächige Karies kommt besonders häufig bei Kindern und jungen Erwachsenen vor. Die sogenannte wilde Karies (rampant caries) gehört zu diesem Typ. Die kariogenen Mikroorganismen haben die besondere Fähigkeit, ein hochmolekulares, wasserunlösliches Dextran aus Saccharose zu bilden* Dieses Dextran gilt als Hauptbestandteil des Zahnbelages, der normalerweise in Verbindung mit Zahnkaries auftritt.In recent years it has been found that the microorganisms, most commonly associated with the formation of multifaceted caries, certain salivars Are streptococci that belong to the group Streptococcus mutans. This multi-faceted tooth decay is particularly common in children and young adults. The so-called rampant caries belongs to this type. The cariogenic microorganisms have the special ability to to form a high-molecular, water-insoluble dextran from sucrose * This dextran is considered to be the main component the plaque that is normally associated with dental caries.

Wenn sich ein Zahnbelag einmal gebildet hat, wird der Bereich unter dem Belag durch die verschiedensten säurebildenden Mikroorganismen bevölkert, die, da sie durchOnce a dental plaque has formed, the area under the plaque becomes acidic in a variety of ways Microorganisms that populate since they are through

209840/1136209840/1136

~2~ 2212H8 ~ 2 ~ 2212H8

den Belag geschützt werden, von den Zahnoberflächen nicht leicht entfernbar sind. Ein Mittel zur Verringerung des Auftretens von Zahnkaries wäre somit die Begrenzung der im Mund gebildeten Dextranmenge oder des Zahnbelageß.the plaque are protected, cannot be easily removed from the tooth surfaces. A means of reducing the The occurrence of dental caries would thus limit the amount of dextran formed in the mouth or the dental plaque.

Verschiedene Mittel wurden zur Bekämpfung der Zahnbelagbildung vorgeschlagen. Die USA-Patentschrift 3 235 4-60 beschreibt die Verwendung gewisser Enzyme wie Pancreatin als wirksames Mittel zur Verhinderung der Zahnbelagbildung. Die Verwendung gewisser.Enzyme, z.B. Dextranase, erwies sich als erfolgreich für den Angriff auf das Dextran, nachdem es sich auf den Zähnen abgesetzt hat. Es wird angenommen, daß die Zerstörung des Dextrans den Zerfall des Zahnbelages und Zahnsteins zur Folge hat und damit zu einem erheblichen Rückgang der Zahnkaries beiträgt.Various means have been suggested to combat plaque build-up. U.S. Patent 3,235-460 describes the use of certain enzymes such as pancreatin as an effective means of preventing plaque formation. The use of certain enzymes, e.g. dextranase, has been shown to be successful in attacking the Dextran after it settles on your teeth. It is believed that the destruction of the dextran Decay of the dental plaque and tartar has the consequence and thus to a significant decrease in dental caries contributes.

Es wurde ferner eine direkte bakterizide Wirkung auf die kariogenen Mikroorganismen vorgeschlagen, um die Zahnkaries zu reduzieren oder zu verhüten. Die USA-Patentschriften 2 921 886 und 3 450 812 beschreiben Alkylmorpholinverbindungen und Stickstoffverbindungen der Bruttoformel ^οΗ,-^ΝΟ..^ als antimikrobielle Mittel, die als Antikariesmittel wirksam sind.A direct bactericidal effect on the cariogenic microorganisms has also been suggested to prevent dental caries to reduce or prevent. U.S. Patents 2,921,886 and 3,450,812 describe alkyl morpholine compounds and nitrogen compounds of the gross formula ^ οΗ, - ^ ΝΟ .. ^ as antimicrobial agents, the are effective as anti-caries agents.

Gemäß der Erfindung wurde nun gefunden, daß eine Anzahl von Verbindungen in oral genommenen Präparaten die Karies wirksam verhindern. Einige dieser Verbindungen sind antimikrobielle Mittel gegen kariogene Streptokokken. Diese Verbindungen haben offensichtlich die Fähigkeit, das Wachstum kariogener Streptokokken zu hemmen oder sie zu vernichten.According to the invention it has now been found that a number of compounds in preparations taken orally reduce tooth decay effectively prevent. Some of these compounds are antimicrobial Agents against cariogenic streptococci. These compounds obviously have the ability to do that To inhibit the growth of cariogenic streptococci or to destroy them.

Andere erfindungsgemäß verwendete Verbindungen aus der Gruppe der oberflächenaktiven Mittel begrenzen das Ausmaß der Belagbildung im Mund. Der V/irkmechanismus, der der Erfindung zugrunde liegt, ist die offensichtliche Fähigkeit gewisser Verbindungen, die Bildung von DextranOther compounds from the group of surface-active agents used in accordance with the invention limit the extent the formation of deposits in the mouth. The mechanism of action on which the invention is based is the obvious capability certain compounds, the formation of dextran

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-5- ■ -2212U8-5- ■ -2212U8

durch die oben genannten Streptokokken zu hemmen.by inhibiting the above-mentioned strep.

Nicht zu trennen von dem Problem der Identifizierung antimikrobieller Verbindungen, die die Zahnkaries wirksam reduzieren, ist die Notwendigkeit, ein Mittel zu finden, das es dem Wirkstoff ermöglicht, im Mund wirksam zu werden. Das Problem wird noch komplizierter durch die Notwendigkeit, daß die Substanz gewisse unerläßliche zusätzliche Eigenschaften hat, z.B. Unbedenklichkeit hinsichtlich der oralen Toxizität, der akuten chronischen Toxizität, der Nicht-Sensibilisierung und der Reizfreilieit bezüglich der Schleimhäute.Inseparable from the problem of identifying antimicrobial compounds that make dental caries effective reduce is the need to find a means that will allow the active ingredient to work effectively in the mouth will. The problem is compounded by the need for the substance to have certain essentials has additional properties, e.g. harmlessness with regard to oral toxicity, acute chronic Toxicity, non-sensitization and irritability regarding the mucous membranes.

Ein wichtiges Merkmal der Erfindung ist die Verwendung von Verbindungen mit niedriger Toxizität, die sich leicht in die verschiedensten oralen Präparate einarbeiten lassen.An important feature of the invention is the use of low toxicity compounds that are easily found can be incorporated into a wide variety of oral preparations.

Die erfindungsgemäß verwendeten Verbindungen haben diese Eigenschaften und können lange Zeit im Mund zurückgehalten werden. Eine Gruppe dieser Verbindungen bilden Wirkstoffe, die sich neuerdings als antimikrobiell gegen kariogene Streptokokken erwiesen haben. Eine weitere Gruppe geeigneter Verbindungen bilden die oberflächenaktiven Mittel.The compounds used in the present invention have these Properties and can be retained in the mouth for a long time. Form a group of these compounds Active ingredients that have recently been shown to be antimicrobial against cariogenic streptococci. Another The surface-active compounds form a group of suitable compounds Middle.

Die erfindungsgemäßen Präparate können die Form von Zahnpasten, Zahnpulvern und Mundwasser u.dergl. haben. Da es jedoch erwünscht ist, daß das aktive Ingrediens lange Zeit im Mund vorhanden ist, können die Präparate auch die Form von Kaugummi, Pastillen oder Drops haben, die sich langsam im Mund lösen.The preparations according to the invention can take the form of toothpastes, tooth powders and mouthwashes and the like. to have. However, since the active ingredient is desired to be in the mouth for a long time, the preparations can also take the form of chewing gum, lozenges or drops that slowly dissolve in the mouth.

Die erfindungsgemäß verwendeten Verbindungen, die sich als äußerst wirksame antimikrobielle Mittel gegen kariogene Streptokokken erwiesen, sind Natriumtripolyphosphat, Natriumhexametaphosphat, das Dinatriiimsalz von 9-o-Carb« oxyphenyl"6-hydroxy~2,4,517-tetrajod-3-isoxanth.onThe compounds used in the invention, which proved to be extremely effective antimicrobials against cariogenic streptococci, are sodium tripolyphosphate, sodium hexametaphosphate, the Dinatriiimsalz of 9-o-Carb "oxyphenyl" 6-hydroxy ~ 1 2,4,5 7-tetraiodo-3-isoxanth .on

2098A0/11352098A0 / 1135

-*- ■ -2212U8- * - ■ -2212U8

(FDSiC Red Nr.3), Natrium-palmitoyl-L~lysin-L-lysinäthylesterdihydrochlorid^ Natrium-palmitoyl-L-lysin~L-lysinamiddihydrochlorid und Hopfenextraktharze (z.B. Lupulon und Ilumulon).(FDSiC Red No. 3), sodium palmitoyl-L ~ lysine-L-lysine ethyl ester dihydrochloride ^ Sodium palmitoyl-L-lysine ~ L-lysine amide dihydrochloride and hop extract resins (e.g. lupulon and ilumulon).

Verbindungen, die eine gewisse Wirksamkeit als antimikrobielle Mittel gegen kariogene Streptokokken zeigen, jedoch nicht in den Rahmen der Erfindung fallen, sind Calciumdihydrogenphosphat, Natriumphosphat, Natriumtrimetaphosphat und L-Lysin-n-doceylesterdihydroChlorid.Compounds showing some effectiveness as antimicrobial agents against cariogenic streptococci, but do not fall within the scope of the invention are calcium dihydrogen phosphate, sodium phosphate, sodium trimetaphosphate and L-lysine-n-doceyl ester dihydrochloride.

Die oberflächenaktiven Verbindungen, die sich als äußerst wirksam bezüglich der Verhinderung der Bildung von Dextran in der Mundhöhle erwiesen, sind Stearylfumarat, Propylenglykolstearatcitrat, Glycerinstearatcitrat, Stearylmonoglyceridylcitrat, Stearoyl-2-lactylat und die löslichen Salze dieser Verbindungen, insbesondere die löslichen Metallsalze. Eine positive Wirksamkeit bezüglich der Verhinderung der Dextranbildung wurde bei den phosphatieren Monoglyceriden, dem Fumarsäureester von Propylenglykolmonostearat und bei den löslichen Salzen dieser beiden Verbindungen festgestellt.The surface active compounds that prove to be extremely effective in preventing the formation of Dextran proven in the oral cavity are stearyl fumarate, Propylene glycol stearate citrate, glycerine stearate citrate, Stearyl monoglyceridyl citrate, stearoyl 2-lactylate and the soluble salts of these compounds, especially the soluble metal salts. A positive effect with regard to the prevention of dextran formation, the phosphated monoglycerides, the fumaric acid ester of propylene glycol monostearate and the soluble salts of these two compounds.

Oberflächenaktive Verbindungen, die sich als unwirksam zur Verhütung der Dextranbildung erwiesen, sind Sorbitanmonostearat (Span 60), Polyoxyäthylensorbitanmonostearat (Tween 60) und Glycerinstearat-oleatmonoester (Myverol, Typ 18-45).Surfactant compounds that have been found to be ineffective in preventing dextran formation are sorbitan monostearate (Span 60), polyoxyethylene sorbitan monostearate (Tween 60) and glycerol stearate oleate monoester (Myverol, Type 18-45).

.Den oralen Präparaten gemäß der Erfindung können die verschiedensten Hilfsstoffe zugesetzt werden. Die oralen Präparate können diese Stoffe in geeigneten Mengen enthalten, vorausgesetzt, daß sie mit den antimikrobiellen oder oberflächenaktiven Verbindungen und den wesentlichen Eigenschaften des oralen Präparats verträglich sind. So ist es möglich, ein oder mehrere antimikrobielle Mittel und eine oder mehrere oberflächenaktive Verbindungen zu kombinieren..The oral preparations according to the invention can A wide variety of auxiliaries can be added. The oral Preparations can contain these substances in suitable quantities, provided they are familiar with the antimicrobial or surfactant compounds and the essentials Properties of the oral preparation are compatible. So it is possible to use one or more antimicrobial agents and combining one or more surface-active compounds.

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Stoffe wie Süßungsmittel, aromatisierende öle, färbende Mittel oder Aufheller, Konservierungsmittel, Alkohole u.dergl. können den oralen Präparaten gemäß der Erfindung ohne weiteres zugesetzt werden. Zahnpflegemittel sollten ferner als größeren Anteil der festen Bestandteile wasserunlösliche Schleif- oder Poliermittel, z.B. Calciumcarbonat, Tricalciumphosphat und Bentonit, enthalten.Substances such as sweeteners, flavoring oils, coloring agents Agents or brighteners, preservatives, alcohols and the like. can the oral preparations according to the invention can easily be added. Dentifrices should Furthermore, as a larger proportion of the solid constituents, water-insoluble grinding or polishing agents, e.g. calcium carbonate, Contains tricalcium phosphate and bentonite.

Bei der Herstellung von Zahnpulvern genügt es gewöhnlich, die verschiedenen festen Bestandteile einschließlich wirksamer Mengen der aktiven Verbindung und Schleifmittel zu einem homogenen Pulver mechanisch zu mischen.In the manufacture of tooth powders, it is usually sufficient to include the various solid ingredients mechanically mixing effective amounts of the active compound and abrasive into a homogeneous powder.

Gemäß der Erfindung hergestelltes Mundwasser enthält gewöhnlich eine wirksame Menge der aktiven Verbindung als Lösung in einem in geeigneter Weise aromatisieren flüssigen Träger, z.B. einem wässrigen Alkohol.Contains mouthwash made according to the invention usually an effective amount of the active compound as a solution to flavor in an appropriate manner liquid carrier, e.g., an aqueous alcohol.

Die Pastillen und Tabletten gemäß der Erfindung werden hergestellt, indem Teilchen der aktiven Verbindung mit Pflanzenschleim und natürlichen oder künstlichen Süßungsmitteln und Aromatisierungsmitteln gemischt werden. Gelatine und Wasser sind ebenfalls eine gute Grundlage für diese bonbonartigen Produkte. Kaugummi kann unter Verwendung eines üblichen Pflanzengummis an Stelle des Pflanzenschleims hergestellt werden. Allen diesen eßbaren Produkten können geeignete füllstoffe zugesetzt werden.The troches and tablets according to the invention are prepared by adding particles of the active compound mixed with phlegm and natural or artificial sweeteners and flavoring agents will. Gelatin and water are also good bases for these candy-like products. chewing gum can be made using a common vegetable gum in place of the vegetable slime. All Suitable fillers can be added to these edible products.

Die oralen Präparate gemäß der Erfindung können nach üblichen bekannten Verfahren hergestellt werden. Das Unterscheidungsmerkmal der Erfindung ist die Einbeziehung einer wirksamen Menge ausgewählter aktiver Verbindungen, die das Auftreten der Zahnkaries vermindern. Diese aktiven Verbindungen können den oralen Präparaten entweder als Ersatz für andere Antikariesmittels die bisher gefunden und verwendet worden sind, oder zusätzlich zu diesen Mitteln zugesetzt werden.The oral preparations according to the invention can be prepared by conventionally known methods. The distinguishing feature of the invention is the inclusion of an effective amount of selected active compounds which reduce the incidence of dental caries. These active compounds may oral preparations s which have heretofore been found and either used as a substitute for other anti-caries agents, or may be added in addition to these means.

209840/1135209840/1135

Die aktiven Verbindungen oder die Kombination von Verbindungen gemäß der Erfindung müssen in den oralen-Präparaten in einer genügenden Menge vorhanden sein, um eine wirksame Konzentration der Verbindungen im Mund zu bilden. Normalerweise müssen die oralen Präparate zu diesem Zweck die antimikrobielle Verbindung in einer Menge von etwa 0,002 bis 5 Gew.-% enthalten. Natürlich ist:es für den Fachmann einleuchtend, daß die erfindungsgemäß verwendeten antimikrobiellen Mittel auf Phosphatbasis und auf Basis von FD & C Red Nr. 3 normalerweise in Mengen am oberen Ende des Bereichs, z.B. in Mengen von 0,3 bis 5% verwendet werdens während die antimikrobiellen Mittel auf Basis von Dipeptiden und Hopfenextraktharzen normalerweise in Mengen am unteren Ende des Bereichs, z.B. in Mengen von 0,002 bis 0,3% verwendet werden.The active compounds or the combination of compounds according to the invention must be present in the oral preparations in an amount sufficient to form an effective concentration of the compounds in the mouth. Usually, for this purpose, the oral preparations must contain the antimicrobial compound in an amount of about 0.002 to 5% by weight. Of course is it apparent to those skilled in the art that are the antimicrobial agents used in this invention based on phosphate and based on FD & C Red No. 3 is normally used, for example in amounts in the upper end of the range in amounts of 0.3 to 5% s. while the dipeptide and hop extract resin antimicrobial agents are normally used in amounts at the lower end of the range, for example in amounts from 0.002 to 0.3%.

Die oberflächenaktive Verbindung oder die Kombination von oberflächenaktiven Verbindungen sollte den oralen Präparaten in einer solchen Menge zugesetzt werden, daß sie in einer wirksamen Konzentration im Mund Vorhanden ist. Normalerweise sind hierzu orale Präparate erforderlich, die die oberflächenaktiven Verbindungen in einer Menge von etwa 0,1 bis 10%, vorzugsweise 0,3 bis 5%, insbesondere etwa 1 Gew.-%, enthalten.The surface-active compound or combination of surface-active compounds should be oral Preparations are added in such an amount that they are present in the mouth in an effective concentration is. Oral preparations are normally required for this, which contain the surface-active compounds in one Amount of about 0.1 to 10%, preferably 0.3 to 5%, in particular about 1% by weight.

Es wurde nachgewiesen, daß die erfindungsgemäß verwendeten antimikrobiellen Verbindungen gegen bekannte kariogene Streptokokken wirksam sind. Die Verbindungen wurden in verschiedenen Konzentrationen in einem Nährmedium auf Basis von Thioglycollat getestet, das mit einer bekannten Menge von kariogenen Mikroorganismen geimpft wurde. Die Kulturen wurden quantitativ mit Kontrollkulturen verglichen, die die antimikrobiellen Verbindungen nicht enthielten. Weitere Kulturen, die äquivalente Mengen von Verbindungen enthielten, die sich als weniger wirksame antimikrobielle Verbindunger gegen kariogene Streptokokken erwiesen, wurden ebenfalls untersucht. Diese Verbindungen fallen jedoch nicht in den Rahmen der Erfindung.It has been proven that the antimicrobial compounds used according to the invention against known cariogenic Streptococci are effective. The compounds were based on in different concentrations in a nutrient medium Tested based on thioglycollate inoculated with a known amount of cariogenic microorganisms. The cultures were compared quantitatively with control cultures that did not contain the antimicrobial compounds contained. Other cultures that contained equivalent amounts of compounds found to be less effective Antimicrobial compounds proven against cariogenic streptococci were also investigated. These connections however, do not fall within the scope of the invention.

209840/1135209840/1135

~7~ 2212H8 ~ 7 ~ 2212H8

Ausgewählte Kulturen wurden.durch Vergleich der Dextranmenge, die in einer Wachstumsperiode von 3 Tagen gebildet wurde, qualitativ bewertet» Bei dieser Testmethode wurden die kariogenen Mikroorganismen in Glasröhrchen gegeben, die Streptococcus Salivarious-Mitis-Agar (Difco) zusammen mit 5% Saccharose, einer Prise Calciumcarbonat und der antimikrobiellen Verbindung (ausgenommen die Ver~ gleichsproben) enthielten. Nach 72 Stunden wurde das unlösliche Material, das sowohl die Mikroorganismen als auch das Dextran enthielt, durch Zentrifugieren abgetrennt und in kaltem 1n-Kaliumhydroxyd gelöst. Diese Lösung wurde dann 2 Stunden gekühlt und zur Entfernung der Mikroorganismen zentrifugiert. Die geklärte Lösung wurde dann mit Äthanol in einer solchen Menge gemischt, daß der Alkoholgehalt auf 70 Gew.-% gebracht wurde, und über Nacht in einem Kühlschrank gehalten; Während dieser Zeit wurde das Dextran ausgefällt. Das ausgefällte Material wurde abgetrennt und die Kohlenhydratmenge (Dextran) visuell verglichen. Die Ergebnisse sind in den folgenden Tabellen zusammengestellt.Selected cultures were determined by comparing the amount of dextran, which was formed in a growth period of 3 days, qualitatively assessed put the cariogenic microorganisms in glass tubes, the Streptococcus Salivarious-Mitis-Agar (Difco) together with 5% sucrose, a pinch of calcium carbonate and the antimicrobial compound (except the Ver ~ same samples) contained. After 72 hours the insoluble material, which was both the microorganisms as well as the dextran contained, separated by centrifugation and dissolved in cold 1N potassium hydroxide. These The solution was then cooled for 2 hours and centrifuged to remove the microorganisms. The clarified solution was then mixed with ethanol in such an amount that the alcohol content was brought to 70% by weight, and kept in a refrigerator overnight; During this time the dextran was precipitated. The precipitated one Material was separated and the amount of carbohydrate (dextran) compared visually. The results are in compiled in the following tables.

Tabelle 1Table 1

p„-Wert vor der Impfung auf 7*2 eingestellt. Zeit: 24 Std. Inoculum: 5 χ 10 (Mikroorganismen FA-l/ml). Temp: 37°C 'p "value before vaccination set to 7 * 2. Time: 24 hours Inoculum: 5 χ 10 (microorganisms FA-l / ml). Temp: 37 ° C '

Verbindung Konzen- Endgültige ZahlConnection Concentric Final Number

tration (Mikroorganismen Gew.-^ FA-l/ml·) tration (microorganisms wt .- ^ FA-l / ml ·)

Kontrolle 1,2 χ 1(T*Control 1.2 χ 1 (T *

Natriumphosphat Na-,ΡΟ^ 1,0 6 χ ΙΟ*'' CaIciumdihydrogenphosphat 1,0 2 χ 10 Ca (H2PO4)2·H2OSodium phosphate Na-, ΡΟ ^ 1.0 6 χ ΙΟ * '' Calcium dihydrogen phosphate 1.0 2 χ 10 Ca (H 2 PO 4 ) 2 · H 2 O

Natriumtripolyphosphat 1,0 3x 10·^ 5^1 Sodium tripolyphosphate 1.0 3x 10 · ^ 5 ^ 1

Natriuinhexametaphosphat 1,0Sodium hexametaphosphate 1.0

209840/1135209840/1135

2212U82212U8

Tabelle 2Table 2

p^-Wert vor der Impfung auf 7,0 eingestelltp ^ value adjusted to 7.0 before vaccination

4
Inoculum: 1 χ 10 (Mikroorganismen PA-l/ml)4th
Inoculum: 1 χ 10 (microorganisms PA-l / ml)

37°c37 ° c

24 Stunden24 hours

Temperatur: Zeit:Temperature: time:

Verbindunglink

Konzentration, Gew.-% Concentration, wt. %

Endgültige Zahl der Mikroorganis men/mlFinal number of microorganisms / ml

Kontrollecontrol Tabelle 3Table 3 11 Gew.-% Weight % <3 χ<3 χ ioy io y NatriumhexametaphosphatSodium hexametaphosphate p„-Wert vor der Impfung auf 7,0 ep "value before vaccination to 7.0 e 0,30.3 1515th IlIl Inoculum: FA-IInoculum: FA-I 0,10.1 9 χ9 χ ΙΟ?ΙΟ? ttdd 11 3 x3 x 109 10 9 NatriumtripolyphosphatSodium tripolyphosphate 0,30.3 3232 ttdd 0,10.1 <3 x<3 x 108 10 8 ItIt 11 2,6 χ2.6 χ 109 10 9 CalciumdihydrogenphosphatCalcium dihydrogen phosphate 0,30.3 4 χ4 χ 105 10 5 ttdd 0,10.1 7 x7 x 107 10 7 ttdd 2 χ2 χ 109 10 9 ingestellthired . Zeit:. Time: 3 Tage3 days Verbindung KonzentraConnection concentra Temp.:Temp .: 37°C37 ° C tion,tion, DextranDextran

Kontrollecontrol

Natriumtripolyphosphat ttSodium tripolyphosphate tt

Calciumdihydrogenphosphat ttCalcium dihydrogen phosphate tt

NatriumhexametaphosphatSodium hexametaphosphate

ItIt

NatriurnphosphatSodium phosphate

1,0 0,1 1,0 0,1 1,0 0,1 1,0 0,11.0 0.1 1.0 0.1 1.0 0.1 1.0 0.1

l·+ O l + O

+■h+ ■ h

2 098 40/11352 098 40/1135

Verbindunglink -Q--Q- 22121482212148 Konzentra
tion, Gew.-#Concentration
tion, wt .- # Verbindunglink 1,01.0 Tabelle 5Table 5 Endgültige Zahl
der Mikroorganis
men/mlFinal number
the microorganism
men / ml Endgültige Zahl ■
der Mikroorganis
men/mlFinal number ■
the microorganism
men / ml Kontrollecontrol Tabelle 4Table 4 \\ Kontrollecontrol 0,30.3 5 χ ioö 5 χ io ö 6 χ IQ6 χ IQ p„.-Wert vorp ".- value before NatriurntripolyphosphatSodium tripolyphosphate der Impfung auf 7,0 eingestelltthe vaccination set to 7.0 1,0 '1.0 ' FDC Red Nr. 3FDC Red No. 3 3 x 102 3 x 10 2 • <:106 • <: 10 6 Inoculum: 2Inoculum: 2 Kontrollecontrol χ 10 (Mikroorganismen SL-l/ml)χ 10 (microorganisms SL-l / ml) FDC Red Nr. 3FDC Red No. 3 3 χ 10"^3 χ 10 "^ 1 χ 106 1 χ 10 6 Zeit:Time: 24 Stunden24 hours Natriumdihydrogenphosphat 1,0Sodium dihydrogen phosphate 1.0 FDC Red Nr. 3FDC Red No. 3 00 2,7 χ 10ö 2.7 χ 10 ö Temperatur:Temperature: 37°C37 ° C NatriumhexametaphosphatSodium hexametaphosphate 00 NatriumhexametaphosphatSodium hexametaphosphate 1 X 101 X 10 Inoculum: 2,Inoculum: 2, 1 χ 10^ (Mikroorganismen FA-l/ml)1 χ 10 ^ (microorganisms FA-l / ml) . Zeit:. Time: 24 Stunden24 hours Temperatur:Temperature: 37°C37 ° C Konzentration,
Gew.-^Concentration,
Wt .- ^ 11 0,10.1 0,010.01

209840/1135209840/1135

Verbindunglink

2212H82212H8

- ίο -- ίο -

Tabelle 6Table 6

Inoculum: ),2 χ 10 (Mikroorganismen FA-l/ml) Zeit: 48 Stunden Temperatur: 37°CInoculum:), 2 χ 10 (microorganisms FA-l / ml) Time: 48 hours Temperature: 37 ° C

Konzentration, Endgültige Zahl Gew. -% der. Mikroorganismen/ml Concentration, final number wt -.% Of. Microorganisms / ml

Kontrollecontrol 2 χ 10b 2 χ 10 b 5 * 10ö 5 * 10 ö Na-palmitoyl-L-lysin-L-lysin-
äthylesterdihydrochlorid 0,001Na-palmitoyl-L-lysine-L-lysine-
ethyl ester dihydrochloride 0.001 <10<10 9 χ 102
I.9 χ 10 2
I. Na-palmitoyl-L-lysin-L-lysin-
amiddihydrochlorid 0,001Na-palmitoyl-L-lysine-L-lysine-
amide dihydrochloride 0.001 <.1O<.1O 8 χ ίο4 8 χ ίο 4 L-Lysin-n-doceylesterdi-
hydrochlorid 0,1L-lysine-n-doceylesterdi-
hydrochloride 0.1 <io6 <io 6 1 χ 10
/ι- 1 χ 10
/ ι- L-Lysin-n-doceylesterdi-
hydrochlorid 0,01L-lysine-n-doceylesterdi-
hydrochloride 0.01 1,7 x 105 1.7 x 10 5 3 χ ίο6 3 χ ίο 6 Tabelle 7Table 7 Inoculum: 1 χ ΙΟ"5 (Mikroorganismen FA-l/ml)Inoculum: 1 χ ΙΟ " 5 (microorganisms FA-l / ml) Zeit: 72 StundenTime: 72 hours Temperatur: 37°CTemperature: 37 ° C Verbindung Konzentra- Dextran Endgültige Zahl
tion, Gew.-% der Mikroorga
nismen/mlCompound Concentric Dextran Final number
tion, wt -.% of micro orga
nisms / ml Kontrolle +++Control +++ Hopfenextrakt
(S.S. Steniner Inc.) 0,01 0Hops extract
(SS Steniner Inc.) 0.01 0 " . 0,005 +". 0.005 + 11 0,001 ++ 11 0.001 ++ 11 0,0005 ++ 11 0.0005 ++

209840/1135209840/1135

2212U82212U8

- li -- li -

Verbindunglink

Tabelle 8Table 8

Inoculum: 5 x 10 (Mikroorganismen FA-l/ml) Zeit: 24 Stunden Temperatur:Inoculum: 5 x 10 (microorganisms FA-l / ml) Time: 24 hours Temperature:

37°C37 ° C

Konzentration, Gew.-% Concentration, wt. %

Endgültige Zahl der Mikroorganismen/ml- Final number of microorganisms / ml-

Kontrolle PDC Red Nr. 3 FDC Red Nr. 3Control PDC Red No. 3 FDC Red No. 3

3 χ ίο"3 χ ίο "

Zwei verschiedene In-vitro-Tests wurden durchgeführt, um die Eignung der oberflächenaktiven Verbindungen nachzuweisen.Two different in vitro tests were performed to determine the Proof of suitability of the surface-active compounds.

Bei der ersten Methode wurde jede oberflächenaktive Verbindung einer Kultur von Streptokokken zugegeben, die in einem Reagenzglas gezüchtet wurden. Die Dextranmenge wurde' dann nach einer Kultivierungsdauer von drei Tagen ermittelt. Bei diesem Test wurden identische kariogene Stämme in Glasröhrchen auf Streptococcus Salivarius-Mitis-Agar (Difco) in Gegenwart von 5· % Saccharose und einer geringen Menge Calciumcarbonat zur Regelung des pH-Wertes gezüchtet. Gleiche Mengen jeweils einer anderen oberflächenaktiven Verbindung wurden zu jedem Glas außer einem Glas gegeben. Nach 72 Stunden war die Mikroorganismen dem Anschein nach ungehindert gewachsen. Das unlös'liche Material, das die Bakterienzellen und das unlösliche Dextran enthielt, wurde dann durch Zentrifugieren abgetrennt. Zur Auflösung des Dextrans wurde kaltes In-KaIiumhydroxyd dem festen Material zugesetzt. Die Lösung wurde zwei Stunden bei etwa 4°C gehalten. Anschließend wurde eine zweite Zentrifugierung vorgenommen, um die Bakterienzellen zu entfernen. Die geklärte Lösung wurde mit Äthanol in einer genügenden Menge gemischt; um die Alkoholkonzentration auf 70°C zu bringen, und über Nacht in einem Kühlschrank gehalten. Während "dieser Zeit wurde das Dextran ausgefällt. Arn nächsten Morgen wurde das ausgefällte Material abgetrennt und der Gehalt an Kohlenhydratfällung'mit Hilfe derIn the first method, each surfactant was added to a culture of streptococci that had been grown in a test tube. The amount of dextran was then determined after a cultivation period of three days. In this test, identical cariogenic strains were grown in glass tubes in Streptococcus mitis Salivarius agar (Difco) in the presence of 5 x% sucrose and a small amount of calcium carbonate for regulating the p H -value. Equal amounts of a different surfactant were added to each glass except for one glass. After 72 hours, the microorganisms appeared to have grown unhindered. The insoluble material, which contained the bacterial cells and the insoluble dextran, was then separated off by centrifugation. Cold potassium hydroxide was added to the solid material to dissolve the dextran. The solution was held at about 4 ° C for two hours. A second centrifugation was then carried out to remove the bacterial cells. The clarified solution was mixed with ethanol in a sufficient amount; to bring the alcohol concentration to 70 ° C and kept in a refrigerator overnight. During this time the dextran was precipitated. On the next morning the precipitated material was separated off and the content of carbohydrate precipitate was determined with the aid of the

209840/1135209840/1135

BAD ORIGINALBATH ORIGINAL

2212U82212U8

Anthronreaktion bestimmt.Anthrone response determined.

Bei der zweiten Methode wurden Chromnickeldrähte in den KuI-turröhrchen gehalten, die mit Thioglykollatmedium, das 0,5 Gew.-^ der oberflächenaktiven Verbindung enthielt, gefüllt waren. Jeder Draht wurde täglich für eine Dauer von 14 Tagen in ein frisches Kultivierungsröhrehen überführt. Die an der Oberfläche der Drähte haftende Dextranmenge wurde dann ermittelt. Die Ergebnisse sind in der folgenden Tabelle zusammengestellt. In the second method, chromium-nickel wires were placed in the culture tubes kept filled with thioglycollate medium containing 0.5 wt .- ^ of the surface-active compound was. Each wire was taken daily for a period of 14 days transferred to a fresh cultivation tube. The amount of dextran adhering to the surface of the wires was then determined. The results are compiled in the following table.

Tabelle 9Table 9

Verbindung Beobachtung BeobachtungConnection observation observation

Test 1 TestTest 1 test

(gleiche Ergebnisse)(same results)

Kontrolle Erhebliche DextranmengeControl Significant amount of dextran

SorbitanmonostearatSorbitan monostearate

(Span 60) "(Span 60) "

Polyoxyathylensorbitan-Polyoxyethylene sorbitan

monostearat (Tween 60) "monostearate (Tween 60) "

Glycerinstearat-oleat-Glycerine stearate oleate

Monoester (Myverol, Typ 18-45) " Phosphatiertes Monoglycerid-Monoester (Myverol, type 18-45) " Phosphated monoglyceride

Mononatriumsalz(Emcol F26-89) Geringe DextranmengeMonosodium Salt (Emcol F26-89) Low level of dextran

Fumarsäureester von Propylenglykolmonostearat "Fumaric acid ester of propylene glycol monostearate "

NatriumstearylfumaratSodium stearyl fumarate

(Pruv) Praktisch kein Dextran(Pruv) Virtually no dextran

Propylenglykolstearat-Propylene glycol stearate

citrat "citrate "

Glycerinstearatcitrat "Glycerine stearate citrate "

Stearylmonoglyceridyl-Stearyl monoglyceridyl

citrat (Sequol) "citrate (Sequol) "

Natriumstearoyl-2-Sodium stearoyl-2-

lactylat (Emplex) "lactylate (Emplex) "

Beispiel 1 In game 1

Ein Kaugummi der folgenden Zusammensetzung wird hergestelltA chewing gum of the following composition is made

209840/1135209840/1135

Saccharose 1239 g 'Sucrose 1239 g '

Chicle-Gummi 413 gChicle gum 413 g

Maisslrup 43° Be 314 gMaisslrup 43 ° Be 314 g

Glycerin ' 15 gGlycerin 15 g

Aromastoffe, Pfefferminzöl 15' gFlavorings, peppermint oil 15 'g

Hopfenextrakt (S.S.Steiner Inc.) ' 5*3 g - -Hop extract (SSSteiner Inc.) ' 5 * 3 g - -

Die Bestandteile wurden wie folgt gemischt: Der Chicle-Gummi wurde 10 Min. in einem 3*8.1-Mischer bei 66°C erweicht. Das Glycerin und der Maissirup wurden dem Chicle-Gummi zugesetzt und 5 Minuten durchgemischt. Nach Zusatz des Zukkers und des Wirkstoffs wurde weitere 5 Minuten gemischt. Das Gemisch wurde dann gekühlt und der Aromastoff zugesetzt und 2 Minuten gemischt. Das Gemisch wurde dann zu Platten geformt und zu Stäben geschnitten.The ingredients were mixed as follows: The chicle gum was softened for 10 minutes in a 3 * 8.1 mixer at 66 ° C. The glycerin and corn syrup were added to the chicle gum and mixed for 5 minutes. After adding the sugar and the active ingredient was mixed for an additional 5 minutes. The mixture was then cooled and the flavor added and mixed for 2 minutes. The mixture was then shaped into plaques and cut into rods.

Beispiel 2Example 2

Ein Kaugummi der folgenden Zusammensetzung wird hergestellt:A chewing gum of the following composition is made:

Saccharose 1239 gSucrose 1239 g

Chicle-Gummi 413 gChicle gum 413 g

Maissirup 43° Be 314 gCorn syrup 43 ° Be 314 g

Glycerin 15 gGlycerin 15 g

Aromastoffe, Pfefferminzöl 15 gFlavorings, peppermint oil 15 g

Natriumstearylfumarat 26,7 gSodium stearyl fumarate 26.7 g

Die Bestandteile werden wie folgt gemischt: Der Chicle-Gummi wurde 10 Minuten in einem 3*8 1-Mischer bei 660C erweicht. Nach Zusatz des Glycerins und des Maissirups wurde 5 Minuten durchgemischt. Dann wurden der Zucker und der Wirkstoff zugesetzt, worauf weitere 5 Minuten gemischt wurde. Das Gemisch wurde gekühlt und der Aromastoff zugesetzt, worauf 2 Minuten durchgemischt wurde. Das Gemisch wurde zu Platten geformt und zu Stäben geschnitten.The ingredients are mixed as follows: The chicle gum was softened in a 3 * 8 1 mixer at 66 ° C. for 10 minutes. After the glycerine and corn syrup had been added, the mixture was mixed for 5 minutes. The sugar and active ingredient were then added, followed by mixing for an additional 5 minutes. The mixture was cooled and the flavor added, followed by mixing for 2 minutes. The mixture was formed into plaques and cut into rods.

Der genaue Wirkmechanismus, nach dem die verschiedenen er-209840/1135 The exact mechanism of action by which the various 209840/1135

findungsgemäß verwendeten Verbindungen das Wachstum von kariogenen Streptokokken hemmen oder diese Mikroorganismen vernichten, ist nicht eindeutig geklärt. Ebenso 1st der genaue Mechanismus, nach dem die verschiedenen oberflächenaktiven Verbindungen die Bildung von Dextran vollständig oder teilweise hemmen, unbekannt. Dies schließt jedoch die Anwendung der Erfindung oder von Variationen oder Modifikationen der* Erfindung nicht aus.compounds used according to the invention the growth of cariogenic Inhibiting streptococci or destroying these microorganisms is not clearly understood. Likewise is the exact mechanism after which the various surface-active compounds completely or partially inhibit the formation of dextran, unknown. However, this includes the application of the invention or variations or modifications of the invention not from.

209840/1135209840/1135

Claims (6)

ΗΚ/ak-wy - 15 - 13.3.1972 PatentansprücheΗΚ / ak-wy - 15 - 13.3.1972 patent claims 1. Oral verwendbare Gemische, die Wirkstoffe mit Langzeitwirkung enthalten für die Verringerung des Kariesbefalls von Zähnen, dadurch gekennzeichnet, daß sie als Wirkstoff'eine wirksame Menge oberflächenaktive Substanzen, die die Bildung von Dextran im Munde verhindern bzw. hemmen und/oder eine wirksame Menge des antimikrobiell-wirkenden Mittels Natriumtripolyphosphat, Natriumhexametaphosphat, Dinatrlumsalz von 9-o-Carboxyphenyl-6-hydroxy-2,4,5i7-tetrajod-3-isoxanthon, Hopfenextraktharze, Natriumpalmitoyl-L-lysin-L-lysinäthylesterdihydroohlorid und/ oder Natrium-palmitoyal-L-lysin-L-lysinamiddihydrochlorid enthalten. '1. Orally usable mixtures containing active ingredients with long-term effects for the reduction of the Caries attack on teeth, characterized in that it is an effective amount of surface-active substance as an active ingredient Substances that prevent or inhibit the formation of dextran in the mouth and / or are effective Amount of the antimicrobial agent sodium tripolyphosphate, sodium hexametaphosphate, disodium salt of 9-o-carboxyphenyl-6-hydroxy-2,4,5i7-tetraiodo-3-isoxanthone, Hop extract resins, sodium palmitoyl-L-lysine-L-lysine ethyl ester dihydrochloride and / or sodium palmitoyal-L-lysine-L-lysine amide dihydrochloride contain. ' 2. Gemisch nach Anspruch 1, dadurch gekennzeichnet, daß es als oberflächenaktive Substanz Stearylfumarat, Propylenglykolstearatcitrat, Glycerinstearatcitrat, Stearylmonoglyceridylcitrat, Stearoyl-2-lactylat, phosphatierte Monoglyceride, den Fumarsäureester von Propylenglykolmonostearat und/oder die löslichen Salze davon enthält.2. Mixture according to claim 1, characterized in that it as a surface-active substance stearyl fumarate, Propylene glycol stearate citrate, glycerine stearate citrate, stearyl monoglyceridyl citrate, stearoyl-2-lactylate, phosphated monoglycerides, the fumaric acid ester of propylene glycol monostearate and / or the soluble ones Contains salts thereof. 3. Gemisch nach Ansprüchen 1 und 2, dadurch gekennzeichnet, daß die oral verwendbare Zubereitung etwa 0,1 bis 10 Gew.-^ an wirksamen oberflächenaktiven Substanzen enthält.3. Mixture according to claims 1 and 2, characterized in that that the orally usable preparation about 0.1 to 10 Gew .- ^ of effective surface-active substances contains. 4. Gemisch nach Anspiü chen 1 bis 3> dadurch gekennzeichnet, daß die oral verwendbare Zubereitung die antimikrobiellen Mittel in einer Menge von 0,002 bis 5 (}ew.-$ enthält.4. Mixture after application 1 to 3> characterized in that the orally usable preparation is the antimicrobial Contains agent in an amount of 0.002 to 5 (} ew .- $. 209840/1135209840/1135 '5. Gemisch nach Ansprüchen 1 bis *l·, dadurch gekennzeichnet, daß die oral verwendbare Zubereitung 0,3 bis '5. Mixture according to claims 1 to * l ·, characterized in that that the orally usable preparation 0.3 to 5 Gew.-Ji an Natriumtripolyphosphat, Natriumhexmetha- -phosphat und/oder Dinatriurasalz von 9-o-Carboxyphenyl· 6-hydroxy-2,4,S,7-tetrajod-3-isoxanthon enthält,5 Weight Ji of sodium tripolyphosphate, sodium hexmetha- phosphate and / or dinatriura salt of 9-o-carboxyphenyl Contains 6-hydroxy-2,4, S, 7-tetraiodo-3-isoxanthone, 6. Verwendung der Gemische nach Ansprüchen 1 "bis 5 als Zusatz zu Kaugummi-Massen.6. Use of the mixtures according to claims 1 "to 5 as Additive to chewing gum masses. 209840/1135209840/1135
DE19722212148 1971-03-15 1972-03-14 Effective mixtures against tooth decay Pending DE2212148A1 (en)

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US05/148,203 US3932603A (en) 1971-05-28 1971-05-28 Oral preparations for reducing the incidence of dental caries

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Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3217379A1 (en) * 1981-05-13 1983-02-03 Colgate-Palmolive Co., 10022 New York, N.Y. AROMA-BASED AQUEOUS ORAL CARE
EP0606599A1 (en) * 1992-12-16 1994-07-20 Miller Brewing Company Oral care compositions containing hop acids
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US4159315A (en) 1977-11-28 1979-06-26 General Mills, Inc. Plaque inhibiting composition and method
US4157385A (en) 1977-11-28 1979-06-05 General Mills, Inc. Plaque inhibiting composition and method
US4148872A (en) 1977-11-28 1979-04-10 General Mills, Inc. Plaque inhibiting composition and method
US4170632A (en) 1977-11-28 1979-10-09 General Mills, Inc. Plaque inhibiting compositions and method
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US4160054A (en) 1977-11-28 1979-07-03 General Mills, Inc. Plaque inhibiting composition and method
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JPH0791177B2 (en) * 1986-07-24 1995-10-04 ライオン株式会社 Oral composition for preventing tartar
AU2090488A (en) * 1987-08-28 1989-03-02 Avantgarde S.P.A. Chewing gum having antitartar activity
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DE3217379A1 (en) * 1981-05-13 1983-02-03 Colgate-Palmolive Co., 10022 New York, N.Y. AROMA-BASED AQUEOUS ORAL CARE
EP0606599A1 (en) * 1992-12-16 1994-07-20 Miller Brewing Company Oral care compositions containing hop acids
US7901713B2 (en) 2001-06-20 2011-03-08 Metaproteomics, Llc Inhibition of COX-2 and/or 5-LOX activity by fractions isolated or derived from hops
US8206753B2 (en) 2001-06-20 2012-06-26 Metaproteomics, Llc Anti-inflammatory botanical products for the treatment of metabolic syndrome and diabetes
US7332185B2 (en) 2001-06-20 2008-02-19 Metaproteomics, Llc Complex mixtures exhibiting selective inhibition of cyclooxygenase-2
US7431948B2 (en) 2001-06-20 2008-10-07 Metaproteomics, Llc Compositions that treat or inhibit pathological conditions associated with inflammatory response
US7270835B2 (en) 2001-06-20 2007-09-18 Metaproteomics, Llc Compositions that treat or inhibit pathological conditions associated with inflammatory response
US7718198B2 (en) 2001-06-20 2010-05-18 Metaproteomics, Llc Treatment modalities for autoimmune diseases
US7919125B2 (en) * 2001-06-20 2011-04-05 Metaproteomics, Llc Modulation of inflammation by hops fractions and derivatives
US8557306B2 (en) 2001-06-20 2013-10-15 Metaproteomics, Llc Compositions that treat or inhibit pathological conditions associated with inflammatory response
US7794757B2 (en) 2001-06-20 2010-09-14 Metaproteomics, Llc Modulation of inflammation by hops fractions and derivatives
US7807203B2 (en) 2001-06-20 2010-10-05 Metaprotemics, Llc Anti-inflammatory pharmaceutical compositions for reducing inflammation and the treatment or prevention of gastric toxicity
US8168234B2 (en) 2001-06-20 2012-05-01 Metaproteomics, Llc Compositions that treat or inhibit pathological conditions associated with inflammatory response
US7815944B2 (en) 2001-06-20 2010-10-19 Metaproteomics, Llc Anti-inflammatory pharmaceutical compositions for reducing inflammation and the treatment of prevention of gastric toxicity
US7820206B2 (en) 2001-06-20 2010-10-26 Metaproteomics, Llc Modulation of inflammation by hops fractions and derivatives
US7901714B2 (en) 2001-06-20 2011-03-08 Metaproteomics, Llp Treatment modalities for autoimmune diseases
US7722903B2 (en) 2001-06-20 2010-05-25 Metaproteomics, Llc Modulation of inflammation by hops fractions and derivatives
US7682636B2 (en) 2001-10-26 2010-03-23 Metaproteomics, Llc Curcuminoid compositions exhibiting synergistic inhibition of the expression and/or activity of cyclooxygenase-2
US7279185B2 (en) 2001-10-26 2007-10-09 Metaproteonics, Llc Curcuminoid compositions exhibiting synergistic inhibition of the expression and/or activity of cyclooxygenase-2
US8846115B2 (en) 2001-11-13 2014-09-30 Metaproteomics, Inc. Anti-inflammatory cyclooxygenase inhibitors
US8158160B2 (en) 2001-11-13 2012-04-17 Eric Hauser Kuhrts Anti-inflammatory cyclooxygenase inhibitors
US8609154B2 (en) 2001-11-13 2013-12-17 Metaproteomics, Llc Anti-inflammatory cyclooxygenase inhibitors
US8486457B2 (en) 2002-10-21 2013-07-16 Metaproteomics, Llc. Compositions that treat or inhibit pathological conditions associated with inflammatory response
US8142819B2 (en) 2002-10-21 2012-03-27 Metaproteomics, Llc Synergistic compositions that treat or inhibit pathological conditions associated with inflammatory response
US8257754B2 (en) 2002-10-21 2012-09-04 Metaproteomics, Llc Synergistic compositions that treat or inhibit pathological conditions associated with inflammatory response
US7790205B2 (en) 2002-10-21 2010-09-07 Metaproteomics, Llc Synergistic compositions that treat or inhibit pathological conditions associated with inflammatory response
US7811610B2 (en) 2003-05-22 2010-10-12 Metaproteomics, Llc Anti-inflammatory pharmaceutical compositions for reducing inflammation and the treatment or prevention of gastric toxicity
US8193201B2 (en) 2004-02-27 2012-06-05 Metaproteomics, Llc Synergistic anti-inflammatory pharmaceutical compositions and related methods using curcuminoids or methylxanthines
US8092846B2 (en) 2004-02-27 2012-01-10 Metaproteomics, Llc Synergistic anti-inflammatory pharmaceutical compositions and related methods using curcuminoids or methylxanthines
US7914831B2 (en) 2004-02-27 2011-03-29 Metaproteomics, Llc Synergistic anti-inflammatory pharmaceutical compositions and related methods using curcuminoids or methylxanthines
US8263139B2 (en) 2005-08-09 2012-09-11 Metaproteonics, Llc Protein kinase modulation by hops and Acacia products
US8815306B2 (en) 2007-03-19 2014-08-26 Metaproteomics, Llc Methods and compositions for promoting bone and joint health
US8475850B2 (en) 2007-05-11 2013-07-02 Metaproteomics, Llc Methods and compositions for heavy metal detoxification
US8241674B2 (en) 2007-05-11 2012-08-14 Metaproteomics, Llc Methods and compositions for heavy metal detoxification

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FR2130275A1 (en) 1972-11-03
NL7203450A (en) 1972-09-19
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IT1035047B (en) 1979-10-20
GB1372932A (en) 1974-11-06

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