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EP3003252A1 - Dérivés de dioxyde de silicium anioniques adsorbés avec des cations pharmaceutiquement actifs pour l'utilisation dentaire - Google Patents

Dérivés de dioxyde de silicium anioniques adsorbés avec des cations pharmaceutiquement actifs pour l'utilisation dentaire

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Publication number
EP3003252A1
EP3003252A1 EP13742506.2A EP13742506A EP3003252A1 EP 3003252 A1 EP3003252 A1 EP 3003252A1 EP 13742506 A EP13742506 A EP 13742506A EP 3003252 A1 EP3003252 A1 EP 3003252A1
Authority
EP
European Patent Office
Prior art keywords
formula
derivative
use according
dental
anionic
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.)
Withdrawn
Application number
EP13742506.2A
Other languages
German (de)
English (en)
Inventor
Massimo Ferrari
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.)
Pavia Farmaceutici SRL
Original Assignee
Pavia Farmaceutici SRL
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 Pavia Farmaceutici SRL filed Critical Pavia Farmaceutici SRL
Publication of EP3003252A1 publication Critical patent/EP3003252A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/13—Amines
    • A61K31/14—Quaternary ammonium compounds, e.g. edrophonium, choline
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/13—Amines
    • A61K31/155—Amidines (), e.g. guanidine (H2N—C(=NH)—NH2), isourea (N=C(OH)—NH2), isothiourea (—N=C(SH)—NH2)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/28—Compounds containing heavy metals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/555—Heterocyclic compounds containing heavy metals, e.g. hemin, hematin, melarsoprol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K33/00—Medicinal preparations containing inorganic active ingredients
    • A61K33/24—Heavy metals; Compounds thereof
    • A61K33/38—Silver; 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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • 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
    • A61K8/25—Silicon; 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/43—Guanidines
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4953—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom containing pyrimidine ring derivatives, e.g. minoxidil
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
    • A61K9/0063—Periodont
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/51—Nanocapsules; Nanoparticles
    • A61K9/5107—Excipients; Inactive ingredients
    • A61K9/5115—Inorganic compounds
    • 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
    • A61K2800/58—Metal complex; Coordination compounds

Definitions

  • the present invention generally refers to a silicon or titanium dioxide derivative of formula (I): (M0 2 ) ⁇ (A m+ ) y , wherein M is Si or Ti, as active ingredient for the preparation of a composition for dental use, e.g. as antibacterial agent in the treatment of oral pathologic conditions .
  • Oral hygiene is the practice of keeping the mouth and teeth clean to prevent dental problems, most commonly, dental cavities, gingivitis, and bad breath. There are also oral pathologic conditions in which good oral hygiene is required for healing and regeneration of the oral tissues. These conditions included gingivitis, periodontitis, and dental trauma, such as subluxation, oral cysts, and following wisdom tooth extraction.
  • chlorhexidine as a component of oral rinses is well documented by many clinical studies, such as among others, Lang Niklausp et al. "Chlorhexidine digluconate, an agent for chemical plaque control and prevention of gingival inflammation", Journal of Periodontal Research (1986) 21:74-89.
  • chlorexidine as active ingredient in some kind of mounthwash, particularly useful in reducing the dental plaque or even as antibacterial agent in general.
  • prolonged use of products containing chlorhexidine can cause stains on teeth, tongue, and gingiva, also on silicate and resin restorations.
  • chlorhexidine is deactivated by most of the anionic compounds commonly used in toothpastes and mouthwashes, such as surfactants and the like. For this reason, chlorhexidine mouth rinses are recommended to be used at least 30 minutes after other dental products.
  • the invention refers to a derivative of formula (I) :
  • (M0 2 ) ⁇ represents an anionic negatively charged dioxide particle comprising tetrahedral Silicon or octahedral Titanium atoms, interconnected by bridging oxygen atoms,
  • a m+ represents a positively charged active species, linked to the anionic silicon or titanium dioxide particle by electrostatic interaction, wherein m is the charge of the active species and it is comprised from 1 to 20, preferably from 1 to 10, Y represents the number of different active species
  • the present use concerns derivatives of formula (I), wherein M is Si, and the (M0 2 ) ⁇ represents anionic silica particles (Si0 2 ) ⁇ .
  • the present use concerns derivatives of formula (I), wherein M is Ti, and the (M0 2 )- represents anionic silica particles (Ti0 2 ) ⁇ .
  • the above derivatives are characterised by the fact that the anionic particles (M0 2 ) ⁇ have an average particle size (ps), intended as average diameter, of at least 200nm, and that the positive A m+ species is adsorbed on the surface of said anionic particles by electrostatic interactions.
  • the present invention also relates to a dental care composition
  • a dental care composition comprising the above indicated derivatives of formula (I) in admixture with at least one physiologically acceptable excipient or carrier, and optionally, with another active ingredient, preferably in the form of toothpaste or mouthcream.
  • dental use means that the present derivatives can be used for the treatment of pathologies of the oral cavity in general, e.g. related to mouth or throat, or even for the treatment of dental diseases, such as gingivitis and the like.
  • M is silicon or titanium
  • a m+ represents a positively charged active species, linked to the selected anionic dioxide particle by electrostatic interaction.
  • positive A m+ species is adsorbed on the surface of the anionic S1O 2 or T1O 2 particles by electrostatic interaction.
  • Y represents the number of the different kind of active species A m+ , co-adsorbed on the same anionic silicon or titanium particle, which can be of the same type or of different chemical nature.
  • the present derivative can present up to 4 different kind of A m+ , co-adsorbed on the same anionic particle.
  • the positively charged active species A m+ is preferably selected from: an antibacterial, an antimycotic, an antiviral and/or sporicidal agent, whereas antibacterial agent is particularly preferred.
  • a m+ is at least one compound selected from the group consisting of: chlorexidine cations, poliexamethylene biguanide hydrochorxde, quaternary ammonium cations, preferably didecyldimethylammonium cations.
  • the invention refers to compounds of formula (I) wherein A m+ can also be a cationic silver complex of general formula [Ag-L] + , wherein L is the chelating moiety (or ligand) .
  • L is selected from optionally substituted 8-mercapto- quinoline hydrochloride, and 2-mercapto-4- (Ci-C 6 -Alk) - pyrimidine, preferably 2-mercapto-4-methylpyrimidine, of formula :
  • Ci-C 6 -Alk means an optionally substituted linear or branched hydrocarbon chain residue, having from 1 to 6 carbon atoms, e.g.: methyl, propyl, iso-propyl, butyl, isobutyl, ter-butyl and the like.
  • the selected cationic silver complex Ag-L is co- adsorbed with chlorexidine cations, preferably gluconate or acetate, to form a multifunctionalised derivatives of formula (I), as described, e.g., in the herein enclosed experimental part.
  • the derivatives for the dental use are derivatives of formula (I) co-adsorbed with chlorexidine and a complex Ag-L, wherein L is the 2-mercapto-4- methylpyrimidine hydrochloride.
  • chlorexidine By the combination of chlorexidine with a silver complex it is in fact possible to use a minor amount of chlorexidine, being the dental action synergically improved by the presence of the Ag + ions from the silver complex. This results allows to overcome the majority of the problems of the prior art, related to the use of chlorexidine, such as stains on teeth, tongue, and gingival, also when a prolonged use is made.
  • the derivatives (I) of the invention have a chemical structure thereby a number of tetrahedral Si or octahedral Ti atoms are interconnected each other by bridging oxygen atoms.
  • the present anionic silicon or titanium dioxide particles are characterised by the fact that they have an average particle size of at least 200nm.
  • the dental use is referred to anionic particles having a diameter of the particles (i.e. the particle size) comprised from 200nm to 2 ⁇ , being an average diameter comprised from 500nm and ⁇ particularly preferred.
  • nano-material is defined as a material having a size ranging from 1 nm to 100 nm (for a general reference about said definition, see e.g.
  • the particle size of the derivatives of the invention is particular relevant because, using particles with size higher than 200 ran allow to adsorb on the same particle an higher number of active A m+ species, even of different chemical nature as above reported. Even further, another advantage in using a ps higher than 200nm, is that it is possible to obtain the present derivatives in form of a powder which can be easily separated by filtration during the industrial preparation .
  • Anionic silica particles (Si0 2 ) ⁇ may be produced, e.g., as reported in the following.
  • Kolbe G. KOLBE, "Dasffyhemische für der Kiesels-ure” Dissertation, Jena (19564)
  • silica particles by reacting tetraethyl silicate in alcoholic solution with water in the presence of bases. With very pure reactants he observed in several cases a slowly proceeding reaction leading to the formation of uniform spherical silica. Later, W. Stober et al .
  • Elemental analysis data of the silica powder obtained by hydrolysis of tetraethoxysilane in ethanol/water/ammonia reveals a content in Nitrogen higher than 0.3%, indicating the presence of ammonium cations which are needed to balance the negative charges at the surface of the solid particle.
  • the observation of a negative value of the zeta potential for silica powder suspensions in water demonstrates and gives a clear picture of the negative charge at the surface of the silica particles.
  • the T1O 2 exists in different allotropic forms: anastase, rutile and brookite, all of them commercially available.
  • the oxide surface is nevertheless characterised by the presence of Ti-OH groups which may undergo deprotonation at a pH higher than 7, to form Ti-CT units, after treatment with a basic substance such as ammonium hydroxide or the like.
  • treatment of Ti0 2 powders with an ethanol-acetone solution containing 10% ammonium hydroxide allow to obtain anionic powders which can be used as a starting substrate for the preparation of antimicrobial derivatives of formula (I), e.g. in the form of a powder.
  • the derivative of formula (I) for the dental use of the invention can be prepared by a process comprising the electrostatic interaction of (Si0 2 ) ⁇ particles having a ps of at least 200nm, with at least one compound able to generate the selected positively charged species A m+ , thus linking the anionic silica particles by electrostatic interactions.
  • the reaction can be carried out by mixing the reactive under stirring at room temperature (e.g. at a temperature comprised from 15 to 40° C) , for a period of time generally comprised from 1 to 3 hours.
  • the derivatives of the invention are useful in oral care or dental sector, in particular as antibacterial, antiviral and/or antimycotic agent for the treatment of oral cavity diseases, preferably gingivitis and periodontitis .
  • the present derivative (I) are also particularly useful to reduce dental plaque.
  • the derivatives (I) are preferably for the use in the treatment of: oral infections, inflammations, oral wounds and ulcers, dental traumas, oral cysts and even in the post- treatment therapy, following the wisdom tooth extraction.
  • the dioxide silica or titanium derivatives of formula (I) can also be employed to reduce dental plaque, or even in dental implantology, e.g. for preparing the implant- abutment junction of dental fixtureor in dental prosthesis or for preparing coronal part of the tooth before insertion of the prosthetic crown.
  • the antibacterial composition are for the use as wound healing agent for oral cavity ulcer derived, e.g. from the use of orthodontic devices.
  • the derivatives (I) are particularly suitable for the preparation of composition for oral care, basically in virtue of their functionalization and versatility.
  • the active species A m+ is electrostatically linked to the anionic dioxide particle, so that the resulting derivative (I) can be admixed e.g. with additives and excipients commonly used in known oral care products.
  • a m+ is chlorexidine
  • the derivatives (I) are also useful as additives for compositions for dental use, thus allowing for instance the preparation of very efficacious oral cavity or throat treatment products, preferably in form of a cream.
  • the invention refers to a dental care composition
  • a dental care composition comprising the derivative of formula (I) as above described, in admixture with at least one physiologically acceptable carrier or excipient, and preferably, also, in admixture with at least another active ingredient.
  • the additional active ingredient can be properly selected among those active ingredient commonly used in the oral care field, where antibacterial, antiviral or antimycotic agent are particularly preferred.
  • compositions of the invention can be selected among those commonly used in the art for the specific dental use, with preference for cationic surfactants.
  • composition of the invention may also further comprise additional ingredients, typically used in common toothpaste preparations, such as, inter alia, surface-active substances, aromatic oils, and sweeteners, humectants, viscosity regulators, ⁇ and the like.
  • the dental composition of the invention is in the form of: toothpaste, cream, gel, foam and mouthwash, whereas cream and gel are particularly preferred.
  • the present invention also refers to a method for the treatment of a dental pathology or disease in a mammal, including man, comprising the oral administration of an effective amount of a derivative of the above indicated formula (I), or a pharmaceutical composition thereof.
  • Example 1 Preparation of (Si0 2 ) " (A m+ ) y , where A m+ is the NH + cation .
  • TEOS tetraethoxysiliane
  • tetrapropoxysilane or tetrabuthoxysilane or tetrapentoxysilane was used as the catalyst. In many cases, it can be applied by adding saturated alcoholic solutions of ammonia to the reaction vessel. In other cases, it can be added directly in aqueous solution.
  • the appearance of white silica is observed within a few more minutes.
  • the reaction can be continued for 120-240 minutes after that the precipitate can be filtered off, washed several times with ethanol and acetone, until neutrality of the washings, and dried in an oven at 60-100 °C for 24 h.
  • the following proportion between reactants is used: 95 % Ethanol, 350 ml; distilled water, 250 ml; concentrated ammonium hydroxide, 100 ml; TEOS 300 ml.
  • the amount of dry powder obtained is of the order of 82 - 83 gr.
  • Elemental analysis of the powder gives 0.32%N, which considering the atomic weight of nitrogen, allow to infer the presence of ca 0.023 negative charges/100 gr of product which are carried by surface Si-0 groups.
  • the % of Nitrogen was observed in the range 0.30-0.40%.
  • Size analysis of the particles composing the powder was done by using a Zetasizer Malvern Instrument 7.01. Measurements were performed on silica powder suspensions in neutral water after ultrasound irradiation for 30 min . The average size distribution obtained was in the range 680 ⁇ 80 nm and the Zeta potential was -62 ⁇ 5 V.
  • Example 2 Preparation of (Si0 2 ) " (A m+ ) Y , where A m+ is the Chlorexidine cation .
  • Size analysis of the particles composing the silica- chlorexidine product gave an average size distribution of 840 + 90 ran, and a Zeta potential was + 25 ⁇ ⁇ V, consistent with the binding of the chlorexidine dication to the negatively charged silica surface.
  • the product was prepared with the procedure outlined in Example 2 by using as a starting material the Si0 2 -Silver Complex adduct prepared according to Example 3.
  • Size analysis of the Si0 2 particles with the electrostatically bound polymeric PHMB gave an average size distribution of 3000 + 360 nra and a Zeta potential was + 73 ⁇ 7 V, consistent with surface binding of the positively charged polymeric cation.
  • Example 6 Antibacterial activity as oral care agent

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Epidemiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Birds (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Physics & Mathematics (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Nutrition Science (AREA)
  • Physiology (AREA)
  • Biomedical Technology (AREA)
  • Nanotechnology (AREA)
  • Optics & Photonics (AREA)
  • Cosmetics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

La présente invention concerne un dérivé de dioxyde de silicium ou de titane de formule (I): (MO2)- (Am+) y, pour l'utilisation dentaire comme agent antibactérien, antiviral ou antimycotique. Les présents dérivés de dioxyde sont particulièrement utiles pour les maladies de la cavité buccale comme la gingivite ou la parodontite, et peuvent de manière adéquate être formulés en mélange avec un ingrédient actif pour soins buccaux connu, comme la chlorhexidine et d'autres. Donc, l'invention concerne aussi une composition de soins dentaires, par exemple sous la forme de pâte ou de crème dentifrice, comprenant au moins les dérivés (I), en mélange avec au moins un support ou un excipient physiologiquement acceptable.
EP13742506.2A 2013-06-06 2013-06-06 Dérivés de dioxyde de silicium anioniques adsorbés avec des cations pharmaceutiquement actifs pour l'utilisation dentaire Withdrawn EP3003252A1 (fr)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/IB2013/054650 WO2014195764A1 (fr) 2013-06-06 2013-06-06 Dérivés de dioxyde de silicium anioniques adsorbés avec des cations pharmaceutiquement actifs pour l'utilisation dentaire

Publications (1)

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EP3003252A1 true EP3003252A1 (fr) 2016-04-13

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EP13742506.2A Withdrawn EP3003252A1 (fr) 2013-06-06 2013-06-06 Dérivés de dioxyde de silicium anioniques adsorbés avec des cations pharmaceutiquement actifs pour l'utilisation dentaire

Country Status (2)

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EP (1) EP3003252A1 (fr)
WO (1) WO2014195764A1 (fr)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2452561B1 (fr) * 2006-10-12 2014-03-26 NM Tech Nanomaterials Microdevice Technology, Ltd. Utilisation d'une composition présentant des propriétés antimicrobiennes

Non-Patent Citations (2)

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See also references of WO2014195764A1 *

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