WO1994019027A1 - Composition de desinfection des verres de contact et mode d'emploi - Google Patents

Composition de desinfection des verres de contact et mode d'emploi Download PDF

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Publication number
WO1994019027A1
WO1994019027A1 PCT/US1994/001607 US9401607W WO9419027A1 WO 1994019027 A1 WO1994019027 A1 WO 1994019027A1 US 9401607 W US9401607 W US 9401607W WO 9419027 A1 WO9419027 A1 WO 9419027A1
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WO
WIPO (PCT)
Prior art keywords
solution
ppm
salt
additional
disinfecting
Prior art date
Application number
PCT/US1994/001607
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English (en)
Inventor
Ben Gu
Kenneth E. Bliznik
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Wesley-Jessen Corporation
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Wesley-Jessen Corporation filed Critical Wesley-Jessen Corporation
Priority to AU62402/94A priority Critical patent/AU6240294A/en
Publication of WO1994019027A1 publication Critical patent/WO1994019027A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L12/00—Methods or apparatus for disinfecting or sterilising contact lenses; Accessories therefor
    • A61L12/08—Methods or apparatus for disinfecting or sterilising contact lenses; Accessories therefor using chemical substances
    • A61L12/14—Organic compounds not covered by groups A61L12/10 or A61L12/12

Definitions

  • a disinfectant for soft contact lenses must possess each of the following properties:
  • This invention is predicated on the surprising discovery that the use of a specific class of compounds, in a specific concentration range, produces compositions fulfilling all of these requirements.
  • the specific compounds are salts of N-acyl-L-arginine esters and their derivatives, as discussed below.
  • the solutions of the invention are fully compatible with both rigid gas permeable and hydrophilic contact lenses during cleaning, wetting, soaking, rinsing and disinfection.
  • CAE-8301 A technical bulletin (CAE-8301) from Ajinomoto Co. , Inc. of Tokyo, Japan, dated 1987 and entitled "Ajinomoto Co., Inc.'s CAE Ethyl N-Cocoyl-L-Arginate
  • PCA Salt states that the cationic surfactant N-cocoyl- L-arginine ethyl ester, DL-pyrrolidone carboxylic acid salt (called “CAE” by its manufacturer) has marked antibacterial and disinfectant activities, and has a low irritancy to skin and eye ucosa. However, this bulletin gives no indication that CAE may be useful for formulating contact lens disinfecting solutions and would be harmless to contact lenses.
  • U.S. Patent No. 5,035,859 discloses a tablet containing 0.75 mg of CAE and 3.75 mg sodium dodecyl sulfate that was dissolved in 7.5 ml of water, thereby creating a solution containing 100 ppm of CAE.
  • this example shows a rather poor activity against Candida albicans. Further, this composition has been found to form precipitates after a few days of storage, and damages hydrophilic contact lenses.
  • Fig. 1 is a view, partially in cross section, of a container in a kit for practicing the invention.
  • Fig. 2 is a view of a lens holder cap which can be used with the container of Fig. 1.
  • the present invention may be summarized, in part, as a method for disinfecting a contact lens, comprising contacting the lens with an aqueous solution comprising from about 2 to about 90 ppm of a salt of an N-fatty acid acyl-L-arginine ester, or derivative thereof.
  • ppm concentration in units of milligrams of a particular component per liter of solution. Unless specified otherwise for a particular value, the term “percent” for a solid composition indicates percentage by weight; for a liquid composition, the term indicates grams per 100 milliliters.
  • fect means the rendering non- viable of substantially all pathogenic microbes that are in the vegetative state, including gram negative and gram positive bacteria, as well as fungi.
  • this invention comprises disinfecting contact lenses with aqueous solutions containing from about 2 to about 90 ppm, preferably about 30 to about 70 ppm, of a salt of an N-fatty acid acyl-L-arginine ester (sometimes abbreviated herein as "AAE”) , or a derivative thereof.
  • AAE N-fatty acid acyl-L-arginine ester
  • RCO is the acylation fatty acid moiety and R' is the esterification alcohol moiety.
  • R will have about 8 to abcvt 20 carbon atoms, in a branched or unbranched configuration.
  • R' typically will have 2 to about 8 carbon atoms.
  • the X in the formula is an acid; this acid can be organic or inorganic (e.g., mineral acids), the choice depending upon the properties required for the molecule.
  • AAE compounds wherein RCO is a fatty acid moiety having 10 to about 18 carbon atoms.
  • Representative commercially available salts of N-fatty acid acyl-L-arginine esters have ethyl ester groups and either hydrochloric acid or DL-2- pyrrolidone-5-carboxylic acid (also known as "PCA” or DL-pyroglutamic acid) anions, and are sometimes referred to by the common names of their fatty acid acyl groups:
  • CAE-PCA cocoyl arginine ester
  • LAE-PCA lauroyl arginine ester
  • Preparation of the hydrochloride compounds may be accomplished by the procedure of R. Infante et al., in "Surface Active Molecules: Preparation and Properties of Long Chain N-Acyl-L- ⁇ -amino- ⁇ -Guanidine Alkyl Acid Derivatives," published in International Journal of Cosmetic Science. Volume 6, pages 275-282, 1984.
  • the PCA salts can be formed using the same procedure, but substituting PCA for the hydrochloric acid.
  • mixtures of the AAE compounds are very useful.
  • the CAE and MAE compounds can have sufficient antimicrobial activity alone, but LAE and PAE compounds generally will be used in combination with another AAE compound or another type of microbicide.
  • the solution also contains buffer to maintain the solution at pH values about 6 to about 8, more preferably about 6.8 to about 7.8 and most preferably about 7.4.
  • Preferred buffers are.borate (e.g., a mixture of boric acid and potassium or sodium borate) and TRIS (tromethamine) .
  • Other buffers which are useful include, without limitation, citrate systems (e.g., sodium or potassium. citrate and citric acid), sodium bicarbonate, and mixed phosphate buffers containing compounds such as Na 2 HP0 4 , NaH 2 P0 4 , K 2 HP0 4 and KH 2 P0 4 .
  • the buffers are present in the disinfecting solution in concentrations of 0.05 to 2.5 percent, preferably 0.1 to 1.5 percent.
  • Disinfecting solutions in accordance with the invention are preferably isotonic to human tears, i.e., they have an osmolarity of 240 to 330 milliosmoles per kilogram of solution (m Osm/kg) .
  • the solutions are rendered isotonic by adding solute, preferably sodium or potassium chloride.
  • solute preferably sodium or potassium chloride.
  • the amount of solute to add depends upon the amounts of other ingredients in the solution. For example, if a high concentration of buffer is already present in the solution, less additional solute will be required.
  • a highly preferred embodiment of the invention involves use of at least one microbicide in addition to the salt of N-fatty acid acyl-L-arginine ester, which has an efficacy-enhancing effect with certain additional microbicides.
  • Preferred additional microbicides include polyhexamethylene biguanide (PHMB), N-(C 8 -C 20 ) alkyl-2-pyrrolidone, and chlorhexidine digluconate.
  • Other additional microbicides include alexidine, polyquaternium-1, hexetidine, bronopol, and hydrogen peroxide in very low concentrations, e.g., 50 to 200 ppm.
  • concentration of additional microbicide will depend on its identity, the desired speed and completeness of disinfection desired, and the concentration of AAE in the solution. General. ⁇ y the preferred concentration of the additional microbicide is from 0.5 to 100 ppm.
  • inventive solutions will preferably also contain a chelating agent, such, as amino carboxylic. acid, compounds or water soluble salts thereof, including ethylenediamine tetraacetic acid (EDTA) , nitrilo- triacetic acid, diethylenetriamine pentaacetic acid, hydroxyethyl ethylenediamine triacetic acid, 1,2- diaminocyclohexane tetraacetic acid, ethylene glycol bis(beta-aminoethyl ether)- N,N,N' ,N'-tetraacetic acid (EGTA) , amino diacetic acid and hydroxyethyl amino diacetic acid.
  • EDTA ethylenediamine tetraacetic acid
  • nitrilo- triacetic acid diethylenetriamine pentaacetic acid
  • hydroxyethyl ethylenediamine triacetic acid 1,2- diaminocyclohexane tetraacetic acid
  • EGTA
  • These acids can be used in the form of their water soluble salts, particularly their alkali metal salts.
  • Especially preferred chelating agents are the di-, tri- and tetra-sodium salts of ethylene diamine tetraacetic acid, most preferably disodium EDTA (Disodium Edetate) .
  • citrates and polyphosphates can also be used in the present invention.
  • the citrates which can be used in the present invention include citric acid and its mono-, di-, and tri-alkaline metal salts.
  • the polyphosphates which can be used include pyrophosphates, triphosphates, tetraphosphates, trimetaphosphates, tetrametaphosphates, as well as more highly condensed phosphates in the form of the neutral or acidic alkali metal salts such as sodium and potassium salts as well as the ammonium salt.
  • Solutions in accordance with the present invention may also include surfactants, such as, tyloxapol, which is 4-(1,1,3,3-tetramethylbutyl)phenol polymer with formaldehyde and oxirane; Pluronic® products (available from BASF Corp., Parsippany, New Jersey U.S.A.) or poloxamers, both being nonionic block copolymer surfactants which are block copolymers of propylene oxide and ethylene oxide; octoxynol or octyphenoxy polyethoxyethanol prepared by reacting isooctylphenol with ethylene oxide; poloxa ine which is a block copolymer derivative of ethylene oxide and propylene oxide combined with ethylene diamine; and nonoxynol nonionic surfactant mixtures prepared by reacting nonylphenols with ethylene oxide.
  • surfactants such as, tyloxapol, which is 4-(1,1,3,3-tetramethylbutyl)phenol polymer with formal
  • surfactants which contain an ethylene oxide repeating group.
  • Most of the above surfactants are described in The Merck Index. Eleventh Edition. Merck & Co., Inc., Rahway, New Jersey U.S.A., 1989.
  • the surfactants can be employed in amounts ranging from about 0.0001 to about 20 percent, preferably from about 0.005 to about 5.0 percent, and more preferably from about 0.025 to about 1 percent.
  • compositions of this invention may also include viscosity increasing agents to provide lubrication to the eye.
  • Suitable viscosity increasing agents include lecithin or cellulose derivatives such as hydroxymethylcellulose, hydroxypropylcellulose and methylcellulose, usually used in amounts from 0.0001 to 20 percent.
  • Yet another desirable additional ingredient is one or more enzymes for removing deposits from the lens.
  • enzymes include proteases.
  • kits comprising a fixed amount of the solid or a container of the pre ixed solution, together with a container for conducting the disinfecting.
  • a container for conducting the disinfecting To prepare the disinfecting solutions, add the solid ingredients to water and agitate until they are completely dissolved. Then adjust the pH of the solution to that desired with, e.g., dilute hydrochloric acid or sodium hydroxide.
  • Disinfection time will vary depending upon the concentration of the salt of N-fatty acid acyl-L-arginine ester and the identity and concentration of the other ingredients, and will generally be from 10 minutes to 8 hours. Disinfection may be carried out at room temperature, i.e., about 20° C. , but other temperatures are satisfactory and higher temperatures may enhance activity.
  • Lens cleaning is enhanced if, prior to the disinfection, the lenses are rubbed with a few drops of the solution of this invention, saline, saliva or a commercial contact lens cleaner such as PLIAGEL® (a product of Alcon Laboratories Inc., Fort Worth, Texas U.S.A.) and then rinsed with any of those, tap water, etc. to dislodge surface contaminants such as mucous, eye makeup, and the like.
  • PLIAGEL® a product of Alcon Laboratories Inc., Fort Worth, Texas U.S.A.
  • the solid compositions of the invention may include conventional lubricants, binders, and excipients which include, but are not limited to glycerol, sorbitol, propylene glycol, polyethylene glycols and dextran.
  • Highly preferable ingredients in the solid compositions, especially tablets, are a combination of sodium carbonate (or bicarbonate) and adipic acid. This combination acts as a lubricant during the tableting process and renders the tablet effervescent for faster dissolution.
  • the term "q.s.” means guantum sufficit or "a sufficient volume” to bring the aqueous solution to specified volume.
  • the disinfecting efficacy was determined by inoculating the test solution with a microbial suspension,at a final concentration of approximately, 1.0 6 colony forming units per ml. Each inoculated solution was then vigorously agitated and kept at ambient temperature.
  • each solution was vigorously agitated and 1 ml aliquots withdrawn and dispensed into 9 ml of neutralizing broth.
  • Ten-fold serial dilutions of each inoculated solution were prepared in neutralizing broth. The solutions were plated out at effective dilutions of
  • PHMB Polyhexamethylene biguanide
  • compositions of Examples 1-6 are listed below.
  • the solutions were prepared by dissolving the solid ingredients in water, forming solutions having the indicated percentages (or ppm) of the component.
  • Examples 1 to 6 show that CAE in combination with typical contact lens solution ingredients is an effective disinfectant. Even at a CAE concentration of only 5 ppm, the solution of Example 6 was able to achieve a 100 fold reduction in S. marcescens bacteria. which is recognized as one of the more difficult organisms to kill.
  • the additional microbicide is N-dodecyl-2-pyrrolidone (Surfadone® LP-300, sold by GAF Chemical Corporation, Wayne, New Jersey U.S.A.), the use of which in contact lens disinfection is disclosed in U.S. Patent 5,035,859 to Gu et al. Examples A, B, C and D are provided for comparative purposes.
  • OptiFree® a commercially available contact lens solution sold by Alcon Laboratories Inc.
  • OptiFree® a commercially available contact lens solution sold by Alcon Laboratories Inc.
  • this solution is described in its package insert as "a sterile, buffered, isotonic, aqueous solution containing a citrate buffer and sodium chloride with edetate disodium 0.05% and POLYQUAD® (polyquaternium-1) 0.001% as preservatives.”
  • sodium chloride is present in sufficient amounts to render the solutions isotonic.
  • An aqueous solution containing a mixture of AAE compounds is prepared, using the following components (concentrations in percent, unless other units are given) and adjusting the final pH to about 7.4:
  • Triton® components are sold by Rohm and Haas Co., Philadelphia, Pennsylvania U.S.A. and are octylphenoxy polyethoxy ethanols.
  • the X-100 is thought to have an average of about 9 ethoxy groups per molecule, while the X-400 has an average of about 40 ethoxy groups.
  • Two useful effervescent tablet formulations for disinfecting contact lenses contain the following ingredients, where the values are expressed in milligrams:
  • the tablets are intended for dissolution in 7.5 ml of normal saline solution. These formulations can be adjusted for use with tap water (e.g., by adding sodium chloride) or for different amounts of liquid. Tablets provide enhanced long-term storage stability and user convenience.
  • the tablets for maximum ease of storing and carrying, can be packaged in the well-known foil backed "blister packs," and dispensed singly as needed.
  • the powdered components may be blended and appropriate unit amounts sealed into pouches or envelopes, for opening by a user at the time of solution preparation; frequently these powder formulations will dissolve readily in aqueous media and do not need to contain gas-forming components.
  • a kit for cleaning contact lenses is shown, in part, in Figs. 1 and 2.
  • Bottle 10 is used to contain the cleaning solution, and is provided with internal ring 12 which indicates the desired liquid filling level. External threads 14 are provided at the top of the bottle.
  • the lens holder cap assembly 16 has internal threading 18 for attachment to the bottle by engagement with the external threads thereon, and an extending platform 20.
  • Hinged lens covers 22 and 24 are mounted onto opposite sides of the platform and can be secured to the platform to retain contact lenses during a cleaning procedure.
  • the platform and lens covers are typically perforated or slotted in appropriate areas to allow free access of disinfecting solution to all surfaces of the lenses.
  • one or both of the covers will be marked to indicate which lens came from the user's left (and/or right) eye.
  • a user places a tablet or powder disinfecting agent (not shown) , which is typically supplied in the kit, into the empty bottle, then fills the bottle to the level of the internal ring with water, saline solution or other specified liquid. If effervescent tablets are not used, the bottle may require shaking or swirling with the cap installed, to insure complete dissolution of the solid agents.
  • the user simply fills the bottle to the indicating ring with pre-prepared disinfecting solution (not shown) , typically provided in the kit. Lenses are installed between the hinged covers and the platform, and the cap is threaded onto the bottle to submerge the lenses in disinfecting solution for a prescribed time. After the procedure, the bottle is emptied and rinsed to remove residual solution.

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  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Apparatus For Disinfection Or Sterilisation (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Eyeglasses (AREA)

Abstract

Les verres de contact se désinfectent à l'aide de solutions renfermant de 2 à environ 90 parties par million d'un sel d'un ester de N-acyl-L-arginine ou d'un dérivé. Les autres éléments constitutifs pouvant être ajoutés à ces solutions sont notamment un élément tampon, un soluté tendant à rendre la solution isotonique, un autre désinfectant et des agents chélatants. L'invention porte également sur une méthode de désinfection des verres de contact à l'aide des solutions visées par l'invention, ainsi que sur des comprimés, des doses et des kits de réalisation de ces solutions.
PCT/US1994/001607 1993-02-26 1994-02-23 Composition de desinfection des verres de contact et mode d'emploi WO1994019027A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU62402/94A AU6240294A (en) 1993-02-26 1994-02-23 Method and composition for disinfecting contact lenses

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US2364993A 1993-02-26 1993-02-26
US08/023,649 1993-02-26

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WO1994019027A1 true WO1994019027A1 (fr) 1994-09-01

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AU (1) AU6240294A (fr)
IL (1) IL108752A0 (fr)
MX (1) MX9401410A (fr)
TR (1) TR27629A (fr)
WO (1) WO1994019027A1 (fr)

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998020913A1 (fr) * 1996-11-13 1998-05-22 Bausch & Lomb Incorporated Procede de decontamination rapide des lentilles de contact
WO1998053681A1 (fr) * 1997-05-31 1998-12-03 Bode Chemie Gmbh & Co. Agent desinfectant exempt d'aldehyde pour surfaces et instruments
US5909745A (en) * 1996-02-26 1999-06-08 Alcon Laboratories, Inc. Use of carbon dioxide and carbonic acid to clean contact lenses
US5965088A (en) * 1997-10-23 1999-10-12 Lever; Andrea M. Method for providing rapid disinfection of contact lenses
US6034081A (en) * 1995-05-30 2000-03-07 Buckman Laboratories International Inc Potentiation of biocide activity using an N-alkyl heterocyclic compound
US6171404B1 (en) 1996-02-26 2001-01-09 Alcon Laboratories, Inc. Use of carbon dioxide and carbonic acid to clean contact lenses
EP1164183A1 (fr) * 2000-06-14 2001-12-19 Menicon Co., Ltd. Solution pour lentilles de contact
WO2003013454A1 (fr) * 2001-08-09 2003-02-20 Lamirsa S.A. Nouveaux systemes conservateurs et utilisation de ceux-ci dans des preparations cosmetiques
US6949218B2 (en) 1996-12-13 2005-09-27 Alcon Manufacturing, Ltd. Use of low molecular weight amino alcohols in ophthalmic compositions
WO2007014580A1 (fr) * 2005-08-01 2007-02-08 Laboratorios Miret, S.A. Systemes de conservation comprenant des tensioactifs cationiques
WO2007112379A2 (fr) * 2006-03-27 2007-10-04 Ethicon, Inc. Composition antimicrobienne
WO2008052031A2 (fr) * 2006-10-24 2008-05-02 Alcon Research, Ltd. Dérivés de 2-pyrrolidone pour la conservation des compositions ophtalmiques, auriculaires et nasales
US7399616B2 (en) 2002-02-01 2008-07-15 Laboratorios Miret, S.A. Enzymatic synthesis of Nα-acyl-L-arginine esters
US7407679B2 (en) 2001-10-25 2008-08-05 Laboratorios Miret, S.A. Use of cationic preservative in food products
EP2082724A1 (fr) * 2001-11-15 2009-07-29 Laboratorios Miret, S.A. Utilisation d'un agent de surface cationique en tant qu'activateur de l'activité anti-microbienne dans des déodorants et des produits de soins oraux
US7662417B2 (en) 2002-05-08 2010-02-16 Laboratorios Miret, S.A. Preservatives and protective systems
WO2010050955A1 (fr) * 2008-10-30 2010-05-06 Esawtech, Ltd. Compositions et procédés microbicides et spermicides à large spectre
US8388986B2 (en) 2001-08-09 2013-03-05 Laboratorios Miret S.A. Use of cationic surfactants in cosmetic preparations
US20140107207A1 (en) * 2007-02-13 2014-04-17 Ajinomoto Co., Inc. Method for Inactivating Viruses With Slightly Acidic Arginine
CN108929247A (zh) * 2018-06-08 2018-12-04 中南大学 一种Nα-烷基酰精氨酸酯抗菌剂及其制备和应用

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991007192A1 (fr) * 1989-11-21 1991-05-30 Schering Corporation Systeme de desinfection de lentilles de contact

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991007192A1 (fr) * 1989-11-21 1991-05-30 Schering Corporation Systeme de desinfection de lentilles de contact

Cited By (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6034081A (en) * 1995-05-30 2000-03-07 Buckman Laboratories International Inc Potentiation of biocide activity using an N-alkyl heterocyclic compound
US6171404B1 (en) 1996-02-26 2001-01-09 Alcon Laboratories, Inc. Use of carbon dioxide and carbonic acid to clean contact lenses
US5909745A (en) * 1996-02-26 1999-06-08 Alcon Laboratories, Inc. Use of carbon dioxide and carbonic acid to clean contact lenses
US6273960B1 (en) 1996-02-26 2001-08-14 Alcon Manufacturing Ltd. Method of cleaning contact lenses using carbon dioxide and carbonic acid
WO1998020913A1 (fr) * 1996-11-13 1998-05-22 Bausch & Lomb Incorporated Procede de decontamination rapide des lentilles de contact
AU725665B2 (en) * 1996-11-13 2000-10-19 Bausch & Lomb Incorporated Method for providing rapid disinfection of contact lenses
US7045095B2 (en) 1996-12-13 2006-05-16 Alcon Manufacturing, Ltd. Use of low molecular weight amino alcohols in ophthalmic compositions
US6949218B2 (en) 1996-12-13 2005-09-27 Alcon Manufacturing, Ltd. Use of low molecular weight amino alcohols in ophthalmic compositions
US8563011B2 (en) 1996-12-13 2013-10-22 Alcon Research, Ltd. Use of low molecular weight amino alcohols in ophthalmic compositions
WO1998053681A1 (fr) * 1997-05-31 1998-12-03 Bode Chemie Gmbh & Co. Agent desinfectant exempt d'aldehyde pour surfaces et instruments
CZ296783B6 (cs) * 1997-05-31 2006-06-14 Bode Chemie Gmbh & Co. Koncentrát dezinfekcního prostredku
US5965088A (en) * 1997-10-23 1999-10-12 Lever; Andrea M. Method for providing rapid disinfection of contact lenses
EP1164183A1 (fr) * 2000-06-14 2001-12-19 Menicon Co., Ltd. Solution pour lentilles de contact
US6417144B2 (en) 2000-06-14 2002-07-09 Menicon., Ltd. Solution for contact lenses
WO2003013454A1 (fr) * 2001-08-09 2003-02-20 Lamirsa S.A. Nouveaux systemes conservateurs et utilisation de ceux-ci dans des preparations cosmetiques
US8388986B2 (en) 2001-08-09 2013-03-05 Laboratorios Miret S.A. Use of cationic surfactants in cosmetic preparations
US7758851B2 (en) * 2001-08-09 2010-07-20 Laboratorios Miret, S.A. Preservative systems and their use in cosmetic preparations
US7407679B2 (en) 2001-10-25 2008-08-05 Laboratorios Miret, S.A. Use of cationic preservative in food products
US7862842B2 (en) 2001-10-25 2011-01-04 Laboratorios Miret, S.A. Use of cationic preservative in food products
EP2082724A1 (fr) * 2001-11-15 2009-07-29 Laboratorios Miret, S.A. Utilisation d'un agent de surface cationique en tant qu'activateur de l'activité anti-microbienne dans des déodorants et des produits de soins oraux
US7399616B2 (en) 2002-02-01 2008-07-15 Laboratorios Miret, S.A. Enzymatic synthesis of Nα-acyl-L-arginine esters
US7662417B2 (en) 2002-05-08 2010-02-16 Laboratorios Miret, S.A. Preservatives and protective systems
WO2007014580A1 (fr) * 2005-08-01 2007-02-08 Laboratorios Miret, S.A. Systemes de conservation comprenant des tensioactifs cationiques
JP2009502181A (ja) * 2005-08-01 2009-01-29 ラボラトリオス ミレ， エス．ア． カチオン性界面活性剤を含む保存系
US10130830B2 (en) 2005-08-01 2018-11-20 Laboratorios Miret, S.A. Preservative systems comprising cationic surfactants
US8604073B2 (en) 2006-03-27 2013-12-10 Ethicon, Inc. Antimicrobial composition
AU2007230597B2 (en) * 2006-03-27 2012-04-26 Ethicon, Inc. Antimicrobial composition
WO2007112379A2 (fr) * 2006-03-27 2007-10-04 Ethicon, Inc. Composition antimicrobienne
WO2007112379A3 (fr) * 2006-03-27 2008-12-18 Ethicon Inc Composition antimicrobienne
CN101573031B (zh) * 2006-03-27 2013-11-20 伊西康公司 抗微生物组合物
CN101573031A (zh) * 2006-03-27 2009-11-04 伊西康公司 抗微生物组合物
WO2008052031A2 (fr) * 2006-10-24 2008-05-02 Alcon Research, Ltd. Dérivés de 2-pyrrolidone pour la conservation des compositions ophtalmiques, auriculaires et nasales
WO2008052031A3 (fr) * 2006-10-24 2009-02-19 Alcon Res Ltd Dérivés de 2-pyrrolidone pour la conservation des compositions ophtalmiques, auriculaires et nasales
US20140107207A1 (en) * 2007-02-13 2014-04-17 Ajinomoto Co., Inc. Method for Inactivating Viruses With Slightly Acidic Arginine
US9462810B2 (en) * 2007-02-13 2016-10-11 Ajinomoto Co., Inc. Method for inactivating viruses with slightly acidic arginine
WO2010050955A1 (fr) * 2008-10-30 2010-05-06 Esawtech, Ltd. Compositions et procédés microbicides et spermicides à large spectre
CN108929247A (zh) * 2018-06-08 2018-12-04 中南大学 一种Nα-烷基酰精氨酸酯抗菌剂及其制备和应用

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Publication number Publication date
IL108752A0 (en) 1994-05-30
MX9401410A (es) 1994-08-31
AU6240294A (en) 1994-09-14
TR27629A (tr) 1995-06-14

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