US3825560A - N-monoacyl derivatives of arginine - Google Patents

N-monoacyl derivatives of arginine Download PDF

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US3825560A
US3825560A US00157584A US15758471A US3825560A US 3825560 A US3825560 A US 3825560A US 00157584 A US00157584 A US 00157584A US 15758471 A US15758471 A US 15758471A US 3825560 A US3825560 A US 3825560A
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arginine
methyl ester
acid
lauroyl
microorganisms
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T Saito
M Takehara
K Yamada
R Yoshida
Y Sasaki
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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/273—2-Pyrrolidones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
    • C07D207/277—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D207/28—2-Pyrrolidone-5- carboxylic acids; Functional derivatives thereof, e.g. esters, nitriles
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/46—Esters of carboxylic acids with amino alcohols; Esters of amino carboxylic acids with alcohols

Definitions

  • FIG. 1A FIG. 1B v 2 A Strain '8' Strain NO.1
  • FIG. 1C '0' Strain u.
  • FIG. 3A HOURS HOURS July 23, 1974 TADAONU SAITO ETAL N-HONOACYL DERIVATIVES 0F ARGININE 3 Sheets-Sheet 3 Filed June 28, 1971 FIGBB FIG. 3A
  • This invention relates to antiseptic, disinfectant, medicinal, preservative, bactericidal, bacteriostatic, germicidal and fungicidal materials and compositions.
  • Corrosive sublimate, cresol, alcohol, invert soap and etc. have been used as disinfectants or antimicrobial detergents in food hygienic field, environment sanitary field and medicinal field.
  • these disinfectants have the following unsatisfactory properties.
  • Corrosive sublimate has powerful disinfectant action, but it has a strong irritation against skin and causes a serious problem in the disposal of waste matters owing to mercury containing material.
  • cresol has high toxicity to men and beasts, while alcohol has weak disinfectant action.
  • invert soap such as Hyamine (Product of Rohm & Haas Co., Inc.) has a powerful disinfectant action, the effect is markedly decreased by co-existence of protein, fat, sodium chloride, or soap, and it has high toxicity to men and beasts (For example, the acute oral toxicity (LD value of Hyamine is 420:25 mg. per kg. of body weight of mice.)
  • a disinfectant incorporating soap or synthetic detergent the so-called deodorant detergent is recommended.
  • deodorant detergents for example hexachlorophene, trichlorocarbanilide, tribromosalicyanilide, tetramethylthiuram disulfide and the like have been practically used.
  • each of these deodorizers has irritation of the skin and is hardly soluble or insoluble in water, and hence it is necessary that these deodorizers are incorporated in a relatively large amount into detergent for purpose to retain their antimicrobial activity. And the use of such a large amount causes further strong irritation on the skin.
  • hexachlorophene or tetramethylthiuram disulfide incorporating detergent has been reported to cause eczematid, sensitization to the skin when exposed to sunlight after its use.
  • usual cationic surfactants which exhibit in general strong antimicrobial action are water soluble, but they cannot be used as deodorizers of detergents, since an insoluble precipitation is formed when they are incorporated in detergent such as soap and thereby antibacterial activity is reduced or disappeared as well as the detergency is markedly reduced.
  • sorbic acid, sodium propionate, dehydro acetic acid, nitrofuran series compounds and etc. have been used as antiseptic agents for food but the amount added of them is restricted from the standpoint of toxicity and so, they can not exert sufiicient antiseptic effect within their allowance of addition.
  • higher alkyl derivatives of peptide containing glutamic acid or basic amino acid have been used as antiseptic agents, but the former is hard to handle because of its very low water solubility, whereas the latter injures the taste of food because of very bitter taste in addition to high cost.
  • An object of the present invention is to provide deodorizers which are suitable to be incorporated into a detergent and which have the desired characteristic properties in that they exert excellent antimicrobial action, cause no irritation to the skin and are effective to enhance cleaning elfect.
  • said mono-N-higher aliphatic basic amino acid derivative s antiseptic, medicinal, preservative, bactericidal, bacteriostatic, germicidal and fungicidal properties.
  • antiseptic, disinfectant, medicinal, preservative, bactericidal, bacteriostatic, germicidal and fungicidal agents which are much secure to men and beasts, comprising at least one mono-N-higher aliphatic acyl basic amino acid derivatives having the following general formula (I), (H) and (III), and salts thereof:
  • salts of these N-higher aliphatic acyl basic amino acid derivatives for example mineral acid salts such as bydrochloride and sulfate, salts with organic acid such as an optically active or inactive a-pyrrolidonecarboxylic acid, an optically active or inactive acidic amino acids (e.g. glutamic acid and aspartic acid), lactic acid, citric acid and acetic acid are taken.
  • organic acid such as an optically active or inactive a-pyrrolidonecarboxylic acid, an optically active or inactive acidic amino acids (e.g. glutamic acid and aspartic acid), lactic acid, citric acid and acetic acid are taken.
  • hydrochloride and salt with DL- or L-u-pyrrolidonecarboxylic acid are suitable from a point of view of crystalline nature.
  • mono-N-higher aliphatic acyl basic amino acid drerivatives are the following N- cocoyl*-N",N-dimethyl-a,-y-diaminobutyric acid methyl ester hydrochloride, N-lauroyl-L-ornithine methyl ester hydrochloride, N"-lauroyl-N ,N"-dimethylornithine benzyl ester hydrochloride, N -palmitoyl-N,N",-N-trimethylornithine methyl ester hydrochloride, N-lauroylbenzyl-N- methyl-ornithine methyl ester hydrochloride, N"-cocoyl*- N-methylornithine methyl ester hydrochloride, N-palmitoyl-N",N-dimethylornithine benzyl ester hydrochloride, N-lauroy1-N-benzyl-N'
  • the first characteristic feature is a fact that the mono- N-higher aliphatic acyl basic amino acid derivatives show a good inhibitory effect against microorganisms which possess relatively strong resistance not only to gram positive bacterium, such as Staphylococcus aureus and Bacillus subtilis, but also to gram negative bacterium, such as Pseudomonws aeruginosa, Escherichia coli and Proteus vulgwris.
  • the bactericidal or inhibitory effect of the compounds of the present invention in comparison with that of Hyamine (product of Rohm & Haas Co., Inc.) and hexachlorophene are illustrated in the Table l.
  • the phenol coeflicient of N-cocoyl-L-arginic ethyl ester pyrrolidonecarboxylate shows high value.
  • phenol coeflicient toward Escherichia coli, Pseudomonas aeruginosa and Staphylococcus aureus is 170, 85 and 250 respectively.
  • Hyamlne (benzethonium chlon'de)--... 50-100 150-200 50-100 25-100 400-500 100-150 800-1,000 G-ll (hexachlorophene) 1,2001,500 1,2001,500 1,000-1,200 250-300 400-500 100-150 800-1,000
  • microorganisms culture media and preparation of cultured cells employed in the test, and the assay method of bactericidal activity are as follows:
  • Eschericida coli (ATCC 3655) Pseudomonas aeruginosa IAM 1002) Proteus vulgaris (IAM 1025) Staphylococcus aureus (ATCC 6538) Bacillus subtilis (ATCC 6633) Candiad albicans (ATCC 10259) Aspergillus niger (ATCC 9642) (b) Culture media employed:
  • Meat extract 1.0%, polypeptone 1.0%, NaCl 0.25% pH 7.0 (used for microorganisms 1-5).
  • Microorganisms 1-6 were cultured statically at at 31 C. for 20 to 24 hr. in test tubes into which are above-mentioned media were poured, while microorganism 7 was cultured at 31 C. for 4 days on the yeast-malt agar slant.
  • the second characteristic feature in this invention is the fact that these non-N-higher alpihatic acyl basic amino acid derivatives possess a powerful antibacterial activity against microorganisms which possess relatively strong resistance to various known antiviral compounds, such as Bacillus subtilis, Candida albicans and Aspergillus niger.
  • various known antiviral compounds such as Bacillus subtilis, Candida albicans and Aspergillus niger.
  • the bacteristatic or inhibitory effect of the compounds of the present invention in comparison with that of nitrofuran series compound, palmitoyl-L-lysil-L- lysin methyl ester dihydrochloride, streptomycin, penicillin and sorbic acid lauroyl sarcosine are illustrated in the Table 2.
  • the third characteristic feature in this invention is the fact that they possess, only a small, or nontoxicity and do not cause any significant skin irritation.
  • the respective LD values of N-lauroyl-L-arginine methyl ester DL-a-pyrrolidone carboxylate and N-cocoyl- L-arginine ethyl ester pyrrolidone carboxylate are 2-3.0 g.kg., 10.75 g./kg. body weight. Accordingly, injuring to men and beasts are scarcely considered.
  • Mono-N-higher aliphatic acyl basic amino acid derivatives or salts thereof can be used in any form of liquid, paste, powder, solid and etc. for the purpose of disinfection and sterilization in food sanitary field, environment public sanitary field, industrial field and farm and gardening field.
  • disinfectant agents but also toilet agents, deodorizer, rinsing agents for shampoo, detergents for vegetables and fruits and disinfectant agents for beasts they are also used.
  • 6 N -lauroyl-L-citrulline methyl 1, 000 1, 000 1, 000 1, 000 1, 000 1, 000 1, 000
  • N layroyl-L-histidine methyl 100-1, 000 100-1, 000 1, 000 1, 000 1, 000 1, 000 1, 000
  • Figures in Tables represent the concentration ('y/ml.) of compounds which causes the growth inhibition of microorganisms.
  • Microorganisms tested, culture conditions and culture medium are as follows:
  • water phase which is easily attacked by microorganisms, is higher than that in oil phase and they show appreciable antiseptic effect even when added in a small amount to cosmetics. And they possess strong penetrating power to a fiber. Accordingly, they may be applied to wide use.
  • Mono-N-higher aliphatic acyl basic amino acid derivatives or salts thereof can be compounded, applied or sprayed according to the shape of soap, synthetic detergent, food, feed, cosmetics, fiber good, leather goods and paint in any form of liquid, powder, or emulsion.
  • antiseptics comprising one or more than two kinds of these esters or salts as an eifective component prevent brewage from hiochi putrefaction rather completely.
  • hiochi putrefaction means that sake (Japanese wine), synthetic sake which contains partially brewing alcohol, or the products of brewing alcohol such as mirin (a sweet kind of sake) becomes impossible to eat and drink because of white muddy and rancidity during the storage, or after the bottling.
  • hiochi putrefaction is caused by Lactobacillus heterohiochi, Lactobacillus japonicus or Lactobacillus homohiochi which comes from brewage.
  • the example 9 and 10 indicate the antibacterial activity of N"-lauroyl-L-arginine-methyl ester pyrrolidone carboxylate in comparison with salicylic acid which has been used habitually for prevention of hiochi putrefaction.
  • these compounds adhered to a mucosa of oral cavity and were disinfectant in it for a long time. From these findings these compounds have marked antibacterial activity against both a bacterium belonging to genus Lactobacillus, a main pathogene of dental caries, and a bacterium belonging to genus Staphylococcus, a main pathogene of alveolar pyorrhea.
  • Table 3 shows the result of antibacterial test of these compounds against genus Lactobacillus, i.e., Lactobacillus fermenti-36 AT CC 9338, and Streptococcus faecalis ATCC 8083, and genus Staphylococcus, Staphylococcus aureus ATCC 65389.
  • Lactobacillus and Streptococcus were measured after 2% gi tanding culture at 37 0., and Staphylococcus was after 48 hr. a.
  • Figures in Table 3 represent the concentration ('y/ml.) of compounds which causes the fifty percents inhibition of bacterial growth.
  • detergents for example, detergents containing predominantly at least one of N-higher acyl glutamate, N-higher acyl aspartate, alkylbenzenesulfonate, higher alkylsulfonate, a-olefin sulfonate and alkylethersulfate are taken.
  • the shape of detergent may be bar, tablet, powder, paste or liquid according to the appearance of a product required.
  • FIGS. 1A to 1H diagrammatically illustrate the bacteriostatic effects of N -lauroylarginine methyl ester a-pyrrolidonecarboxylate of this invention against respective strains of microorganisms when added to culture media for the eight strains together with soap;
  • FIGS. 2A to 2D illustrate the bacteriostatic effects of the compound of FIGS. 1A to 1H in cooperation with a synthetic detergent when added to culture media of the strains illustrated in FIGS. 1A, 1C, 1E, and 1G respectively.
  • FIGS. 3A to 3C diagrammatically illustrate the bacteriostatic effects of a milled soap containing the same compound of the invention when added to culture media of the strains illustrated in FIGS. 1A, 10, and 1G.
  • EXAMPLE 1 Effect of 0.1% -cocoyl-L-arginine ethyl ester-pyrrolidone earboxylate (CAE-P) on fingers disinfection and washing was examined.
  • CAE-P -cocoyl-L-arginine ethyl ester-pyrrolidone earboxylate
  • EXAMPLE 4 The O/W type cold cream was prepared as follows.
  • control cold cream containing 33 ml. of water was also prepared in the same way.
  • the newly prepared Cream Containing Lysine derivative caused a good emulsion and any change of the quality could not be found on storage at 30 C. and at moisture 90% during two months.
  • the control cream showed the growth of mold and resulted in coloration.
  • control toilet water containing polyoxyethylene sorbitan monolaurate instead of arginine derivative was prepared in the same Way.
  • the control toilet water showed the growth of mold.
  • the control assorted feed showed the growth of mold and a putrid smell.
  • EXAMPLE 7 0.5 ml. of aqueous 3% N"-lauroyl-L-arginine ethyl ester DL-a-pyrrolidone carboxylate was sprayed per 100 cm? of surface of dressed oxhide.
  • EXAMPLE 8 The grams of N N -dimethyl N"-lauroyl-DL-ornithine ethyl ester was dissolved homogeneously in 500 g. of water emulsion type paints consisting of part of 50% vinyl chloride emulsion, 70 part of titanium white, 10 part of silicic anhydride, part of calcium carbonate, 30 part of aqueous 10% polyvinyl alcohol, 1 part of ammonium polyacrylate, 1 part of tween 40, and 100 part of water.
  • water emulsion type paints consisting of part of 50% vinyl chloride emulsion, 70 part of titanium white, 10 part of silicic anhydride, part of calcium carbonate, 30 part of aqueous 10% polyvinyl alcohol, 1 part of ammonium polyacrylate, 1 part of tween 40, and 100 part of water.
  • EXAMPLE 9 (LD orally in rat: 0.9 g./kg.) was used as a control in the example.
  • Sake A did not turn sour at all even after six months, while Sake B began to turn sour virtually after a month.
  • EXAMPLE ll Kamoboko was prepared according to a known method by employing the following components; 70.0% of frozen fish meat, 2.6% of sodium chloride, 0.3% of HI-ME (Product of Ajinomoto Co., Inc., Mixture of sodium inosinate and sodium glutamate), 5.5% of egg albumin, 2.1% of sucrose, 13.8% of starch and 7.0% of cold water.
  • HI-ME Product of Ajinomoto Co., Inc., Mixture of sodium inosinate and sodium glutamate
  • egg albumin 2.1% of sucrose, 13.8% of starch
  • 7.0% of cold water 7.0% of cold water.
  • AF-2 Volo Pharmaceutical Co., Nitrofuran compounds
  • EXAMPLE 12 The tooth paste were prepared by mixing such components as written in the following. Percent by Weight Dicalcium phosphate 2H O 44.5 Gum tragancanth 2.0 Glycerol 18.5 N -cocoyl-L-arginine ethyl ester DL-ix-pyrrolidone carboxylate 3.0 Saccharin 0.4 Flavoring material 1.0 Water 30.6
  • EXAMPLE 13 The wet dentifrice was prepared by mixing such components as shown in the following table.
  • N -Lauroyl L arginine methyl ester DL-oc-pyrrolidone-carboxylate (referred to as DL-I) was added to 2.0 g. of fatty acid soap material in an amount given in Table 6 and the mixture was dissolved in 100 ml. of the culture medium shown in Table 7, and then was adjusted to a pH of between 6.2 and 7.3. 4 ml. of the respective solutions was inoculated with each of the eight kinds of microorganisms shown in Table 2 and cultivated under the condition shown in Table 2. The growth of microorganisms was estimated by increased turbidity of the culture solution and was verified by measuring at times absorbance (optical density) at 560 m with a spectrophotometer.
  • A-H microorganisms Eight kinds of microorganisms are respectively referred to as A-H microorganisms hereinafter.
  • N -Lauroyl L (or DL) arginine methyl ester L- a-pyrrolidone-carboxylate (referred to as L-I or DL-I respectively) was added to 2 g. of monosodium N-cocoyl- L-(or DL)-glutamate (referred to as L-II or DL-II respectively) in an amount given in Table 8. Subsequently, inhibitory tests against various microorganisms were carried out according to the similar manner in Example 14.
  • DL-I N-lauroyl DL arginine methyl ester L-apyrrolidone carboxylate
  • Example 14 2.0 g. of each of samples was scraped from the respective products, i.e., the bar soap added with DL-I and one added with no DL-I, and dissolved respectively in 100 ml. of culture solution as in the Example 14. 4 ml. of the solution was inoculated with the microorganisms shown in Table 2 and cultivated under the same conditions. The growth of microorganisms was estimated from the turbidity of the culture solution, which was measured using a spectrophotometer according to the similar manner as in Example 14.
  • the culture medium added with DL-I was recognized to exhibit an inhibitory effect against all of the A-H strains. Only the results of inhibitory test to the 13 A, C and G strains were shown in FIG. 3 wherein a dotted line means the case where DL- I was added and a line means the case where DL-I Was not added. It may be seen that the soap containing DL-I is elfective in inhibiting the growth of microorganisms as compared with the soap not containing DL-I and especially it exhibits a marked inhibitory eflect against A microorganism.
  • EXAMPLE 17 10 Parts of sodium sulfate was mixed with 90 parts of sodium dodecyl sulfate (referred to as SDS) and N- lauroyl-N, 'N-dimethyl-DL-ornithine methyl ester lactate (referred to as DL-II'I) was added thereto in an amount given in Table 9 to prepare shampoo composition.
  • SDS sodium dodecyl sulfate
  • DL-II'I N- lauroyl-N, 'N-dimethyl-DL-ornithine methyl ester lactate
  • EXAMPLE 18 5 Parts of each of the eleven 'kinds of mono N-higher aliphatic acyl basic amino acid derivatives shown in Table 10 was sutficiently compounded together with 100 parts of soap material and with 1-3 parts of water using a roller. The mixture was warmed to 50-55 C. and extended into a bar soap having 25 mm. in diameter using a prodder, and the bar soap was stamped.
  • N-Myristoyl-L-lysine methyl ester hydrochloride 2. -Myristoyl-L-lysine amide hydrochloride 3 N-Palmitoyl N,N dimethyl-Irlysine methyl ester hydrochloride N Lauroyl-N;N ,N"-trimethyl-DL-ornithine methyl ester hydrochloride N-cocoyl-N"-methyl-DI.-ornithine methyl ester hydrochloride N -Palmitoyl-N",N"-dimethy1 DL ornithine benzylester hydrochloride N"-Lauroyl-N-benzyl-N -methyl-DL-ornithine methyl ester hydrochloride 8.
  • N-cocoyl-N",N"-dimethyl DL a,'y-diaminobutyric acid methyl ester hydrochloride N,N"-dimethyl-N -hydrogenated tallowyl DL ornithine ethyl ester hydrochloride
  • N-hydrogenated tallowyl arginine methyl ester L-apyrrolidone carboxylate 11.
  • the absorbance of the culture solution added with the bar soap for control in 10 hours after cultivation was 0.80, while the absorbance of any culture solutions added with the bar soaps containing the additives in the that time was below 0.10.
  • the precipitate was filtered and it was dissolved in 400 ml. of ethanol.
  • the ethanol solution was added slowly into 800 ml. of aqueous ammonia under cooled to 0 C.
  • the precipitate of separates out was filtered and dried.
  • a compound as set forth in claim 1 which is an ester of N-monoacyl arginine or a salt of said ester.
  • ester is a lower alkyl ester of N-lauroyl arginine.

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Cited By (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3995051A (en) * 1974-07-17 1976-11-30 Stanley Drug Products, Inc. Methods and compositions for inducing resistance to bacterial infections
US5100655A (en) * 1987-12-18 1992-03-31 Ajinomoto Co., Ltd. Arginine derivatives and cosmetic compositions containing the same
WO1996024578A1 (es) * 1995-02-09 1996-08-15 Consejo Superior Investigaciones Cientificas (Csic) TENSIOACTIVOS CATIONICOS GEMINALES DEL TIPO N?αNφ BIS(Nα¿-ACIL-ARGININA)α,φ DIAMINO ALQUIL DICLORHIDRATOS COME AGENTES ANTIMICROBIANOS
US6034137A (en) * 1996-10-22 2000-03-07 Syntex (U.S.A.) Inc. Cationic lipids for gene therapy
EP1283014A1 (de) * 2001-08-09 2003-02-12 Nutrinova Nutrition Specialties & Food Ingredients GmbH Konservierte Futtermittel und Verfahren zu ihrer Herstellung
WO2003034842A1 (en) * 2001-10-25 2003-05-01 Laboratorios Miret, S.A. Use of cationic preservative in food products
US20030162838A1 (en) * 2001-08-21 2003-08-28 Ajinomoto Co., Inc. Bactericide, antiseptic, dermally applicable composition, washing composition, antibacterial fiber aggregate, method for eradicating a microorganism, and method for inhibiting the proliferation of a microorgamism
US20040122095A1 (en) * 2001-04-28 2004-06-24 Bonaventura Joan Seguer Antimicrobial composition comprising potassium sorbate and lae
US20040175350A1 (en) * 2001-08-09 2004-09-09 Urgell Beltran Joan Baptista Use of cationic surfactants in cosmetic preparations
US20040258630A1 (en) * 2003-06-23 2004-12-23 Boyd Thomas J. Antiplaque breath freshening consumable film
US20040258629A1 (en) * 2003-06-23 2004-12-23 Boyd Thomas J. Antiplaque confectionery dental composition
US20050031551A1 (en) * 2003-06-23 2005-02-10 Michael Prencipe Stable dentifrice compositions
US20050175747A1 (en) * 2002-05-08 2005-08-11 Joan Seguer Bonaventura Preservatives and protective systems
US20060003427A1 (en) * 2002-02-01 2006-01-05 Bonaventura Joan S Enzymatic synthesis of n (alpha)-acyl-l-arginine esters
WO2006085859A1 (en) * 2005-01-31 2006-08-17 Stockel Richard F Biocidal compositions
US20060193791A1 (en) * 2003-06-23 2006-08-31 Boyd Thomas J Antiplaque oral care compositions
US20100056628A1 (en) * 2006-09-07 2010-03-04 Stockel Richard F Preservative compositions
US20100173993A1 (en) * 2003-02-06 2010-07-08 Sawyer Anthony J Controlled release biocidal salts
US7758851B2 (en) 2001-08-09 2010-07-20 Laboratorios Miret, S.A. Preservative systems and their use in cosmetic preparations
US8193244B1 (en) 2008-05-29 2012-06-05 Nevada Naturals, Inc. Antimicrobial agents
US8795638B1 (en) 2003-08-26 2014-08-05 Nevada Naturals Inc. Compositions for dental care
US8834857B1 (en) * 2011-01-18 2014-09-16 Nevada Naturals Inc. Deodorizing and skin cleaning
US8926997B1 (en) 2003-02-06 2015-01-06 Richard F. Stockel Polymeric biocidal salts
US9023891B2 (en) 2008-05-29 2015-05-05 Nevada Naturals, Inc. Synergistic antimicrobial agents
EP3251697A4 (en) * 2015-01-27 2018-08-22 Ajinomoto Co., Inc. Method for controlling skin penetration

Families Citing this family (4)

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Publication number Priority date Publication date Assignee Title
JPS514125A (en) * 1974-06-27 1976-01-14 Mitsubishi Chem Ind N22 ashiru ll arugininesuterumatahasono sanfukaenno seizoho
JPS51137638U (es) * 1975-04-30 1976-11-06
JPS5575104U (es) * 1978-11-20 1980-05-23
JPS59179349U (ja) * 1983-05-17 1984-11-30 株式会社村田製作所 サ−ミスタ温度センサ

Cited By (39)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3995051A (en) * 1974-07-17 1976-11-30 Stanley Drug Products, Inc. Methods and compositions for inducing resistance to bacterial infections
US5100655A (en) * 1987-12-18 1992-03-31 Ajinomoto Co., Ltd. Arginine derivatives and cosmetic compositions containing the same
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FR2074495A5 (es) 1971-10-01
IT1049519B (it) 1981-02-10
DE2064086A1 (de) 1971-07-01
GB1290067A (es) 1972-09-20
JPS4926046B1 (es) 1974-07-05

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