EP4466094A1 - Glycosylbarbiturat-geliermittel - Google Patents

Glycosylbarbiturat-geliermittel

Info

Publication number
EP4466094A1
EP4466094A1 EP23701452.7A EP23701452A EP4466094A1 EP 4466094 A1 EP4466094 A1 EP 4466094A1 EP 23701452 A EP23701452 A EP 23701452A EP 4466094 A1 EP4466094 A1 EP 4466094A1
Authority
EP
European Patent Office
Prior art keywords
group
chosen
organic
oil
mixture
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
EP23701452.7A
Other languages
English (en)
French (fr)
Inventor
Sami Halila
Robin BRAHMI
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.)
Centre National de la Recherche Scientifique CNRS
Original Assignee
Centre National de la Recherche Scientifique CNRS
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 Centre National de la Recherche Scientifique CNRS filed Critical Centre National de la Recherche Scientifique CNRS
Publication of EP4466094A1 publication Critical patent/EP4466094A1/de
Pending legal-status Critical Current

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
    • B01J13/0052—Preparation of gels
    • B01J13/0065—Preparation of gels containing an organic phase
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/042—Gels
    • 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
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • 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
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • 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
    • A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q13/00—Formulations or additives for perfume preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • A61K2800/48—Thickener, Thickening system

Definitions

  • the subject of the present invention is new gelling agents based on glycosylbarbiturates, referred to by the scientific name as p-C-glycoside pyrimidinetrione, as well as a process for preparing an organogel or oleogel by the use of said gelling agents based on glycosylbarbiturates.
  • Organogelators are small organic molecules capable of texturing and even gelling all kinds of organic solvents or oily phases, even at relatively low mass concentrations (less than 1% by mass).
  • organogelators To date, there are many molecules that can be used as organogelators, but these have a number of drawbacks.
  • organogelators require multiple steps, as well as the use of solvents and/or toxic reagents.
  • most of these organogelators are hydrophobic in nature, which makes them poorly soluble in an aqueous medium and therefore not “leachable”.
  • their chemical and enzymatic stability is an obstacle to their development.
  • organogelators of a polymeric nature such as ethylcellulose also have the disadvantage of leaving a film after their application.
  • organogelator is often application specific and organogelators have the sole function of texturing or gelling.
  • organogelator that does not have the aforementioned drawbacks, and therefore in particular to provide an organogelator compound of a biosourced nature, which can be easily synthesized in an eco-responsible manner and which is chemically and enzymatically stable.
  • the present invention therefore aims to provide an organogelator that can be synthesized in a single step and under environmentally friendly conditions, in particular in the presence of aqueous solvents, without the formation of by-products, easy purification and a quantitative yield.
  • the present invention also aims to provide an organogelator that is perfectly soluble in water and therefore washable at the end of application for dermal treatments, for example.
  • the present invention also aims to provide an organogelator which is chemically and enzymatically stable, and optionally with an easily adjustable capacity for gelling.
  • the present invention relates to the use as gelling or texturizing agent of a compound of general formula (I) below: in which :
  • Sacc represents a monosaccharide or polysaccharide comprising up to 20 sugar units, in pyranose and/or furanose form and of the L and/or D series, said mono- or polysaccharide having at least one free hydroxyl function;
  • - Xi + represents a cation chosen from the group consisting of: Na + , Li + , K + , + NR 3 R 4 R 5 R 6 , R 7 -NH 3 + , + PR 3 R 4 R 5 R 6 and + SR 3 R 4 R 5 ,
  • R 3 , R 4 , R 5 and R 6 identical or different, representing a (Ci-Csojalkyl) group, optionally including at least one unsaturation, said alkyl group being optionally substituted by at least one (Ce-Cio)aryl group, in particular a phenyl group,
  • R 7 representing a (Ci-Csojalkyl) group, optionally including at least one unsaturation, said alkyl group being optionally substituted by at least one (Ce-Cio)aryl group, in particular a phenyl group,
  • R 2 represents H, methyl, or a (Ci-Csojalkyl) group optionally including at least one unsaturation, said alkyl group being optionally substituted by at least one (Ce-Cio)aryl group, in particular a phenyl group, as well as its tautomeric forms.
  • the compounds used as texturizing or gelling agents according to the invention are C-glycoside derivatives which are chemically and enzymatically stable thanks to the non-natural C-glycosidic bond.
  • organogelators according to the invention can be used, for example, in cosmetic and perfume compositions or pharmaceutical or dermo-pharmaceutical compositions, but also in the food-processing field or even in the industry of lubricants, paints, construction or for the maintenance of paint canvases.
  • Texture agents are additives present in cosmetic, food or other formulas in order to increase the consistency, viscosity and sensoriality of the finished products. Texturizing agents are in particular synthetic polymers such as polyacrylates, biosourced polymers such as polysaccharides and their derivatives, gums or lipids derived from oils or butters, esters or waxes.
  • a gelling agent can be texturizing and this will depend on its concentration in the medium. Below its minimum gelling concentration for a given fatty phase, it will be texturizing and above or equal to it will be gelling.
  • group (C t -C z ) is meant a group comprising a carbon chain which may have from t to z carbon atoms, for example Ci-Ce a carbon chain which may have from 1 to 6 carbon atoms.
  • alkyl designates aliphatic hydrocarbon-based, saturated, linear or branched groups comprising, unless otherwise stated, from 1 to 20 carbon atoms.
  • alkyl designates aliphatic hydrocarbon-based, saturated, linear or branched groups comprising, unless otherwise stated, from 1 to 20 carbon atoms.
  • the alkyl groups according to the invention can be interrupted by at least one unsaturation.
  • the alkyl groups of the invention can also be substituted by at least one aryl group.
  • the aryl groups are cyclic aromatic groups comprising between 6 and 10 carbon atoms.
  • aryl groups mention may be made of phenyl or naphthyl groups.
  • R 3 , R 4 , R 5 and R 6 which are identical or different, represent a (Ci-C2o)alkyl group, or a benzyl group.
  • R 7 represents a (Ci-C2o)alkyl group.
  • R 2 represents H or methyl, preferentially methyl.
  • Xi + represents a cation chosen from the group consisting of: Na + , Li + and K + , and is preferentially Na + .
  • the Xi + cation can be chosen from polycharged derivatives such as, for example, polyammonium ions.
  • Sacc is selected from the group consisting of D-glucose, D-galactose, D-mannose, D-xylose, D-lyxose, L-fucose, L-arabinose, L-rhamnose, D-glucuronic acid, D-galacturonic acid, D-iduronic acid, N-acetyl-D-glucosamine, N- acetyl-D-galactosamine, D-maltose, D-lactose, D-cellobiose, D-maltotriose, D-iduronic acid, D-glucuronic acid with a hexosamine selected from D-galactosamine, D-glucosamine, N-acetyl-D-galactosamine or N-acetyl-D-glucosamine, xylobiose and its oligomers (from xylotriose to xylohexa
  • Sacc is D-glucose.
  • the C-glycoside derivatives of formula (I) according to the present invention can be prepared, for example, according to the methods described by Gonzales M.A. et al. Carbohydrate Research 1986, 158, pp58-66 and by Wulff G. et al. Carbohydrate Research 1994, 257, pp81-95.
  • the aforementioned preferred glycosylbarbiturate is for example obtained in a single synthesis step in water and characterized by a glucose unit linked by a C-glycosidic bond to N,N-dimethylbarbituric acid. Its purification is obtained by simple precipitation of the reaction medium with a quantitative yield, making its production easy and practical from an industrial point of view.
  • the starting reagents for the preparation of this molecule are commercially available.
  • the compounds of the invention texturize to the point of gelling both organic solvents of different polarities and oils and their gelation capacity can be easily modulated by the nature of the associated cationic counterion. Gelation can be induced by ultrasound, simple mixing or by a cycle of heating followed by cooling to room temperature, as explained later.
  • the compound of formula (I) is used as a gelling agent for an organic liquid or mixture of liquids, said organic liquid being chosen from organic solvents and oils.
  • an organic liquid is a liquid with a carbon chain or containing carbon. As indicated above, it can be an organic solvent, an oil or a mixture thereof.
  • the organic liquid is an organic solvent chosen from the group consisting of alcohols, ketones, aliphatic, aromatic or halogenated hydrocarbons, esters, nitrogen derivatives, ethers, silicones, aliphatic carboxylic acids and their ester derivatives, amides lipids or glycerides.
  • the organic solvent is chosen from ethanol, propanol, glycerol, butanol, octanol, isopropanol, anisole, octyldodecanol, ethyl acetate, acetone, tetrahydrofuran, oleic acid, linoleic acid, palmitic acid and adipate, stearate or caprate esters.
  • the organic liquid is an oil chosen from vegetable or animal oils, natural or synthetic mineral oils.
  • the oil is chosen from rapeseed oil, castor oil, jojoba oil, lavender essential oil, palm oil, olive oil, sunflower oil, paraffin or liquefied petroleum.
  • the organic liquid is an organic solvent chosen from ethanol, propanol, butanol, glycerol, octanol, isopropanol, anisole, ethyl acetate and tetrahydrofuran, or an oil chosen from rapeseed oil or lavender essential oil (HE lavender).
  • organic solvent chosen from ethanol, propanol, butanol, glycerol, octanol, isopropanol, anisole, ethyl acetate and tetrahydrofuran, or an oil chosen from rapeseed oil or lavender essential oil (HE lavender).
  • the present invention also relates to the aforementioned use, in which the compound of formula (I) is used as a texturizing or gelling agent for a mixture of organic liquids, preferably comprising at least one oil and/or at least one organic solvent.
  • a mixture for example, mention may be made of a mixture comprising essential oil of lavender and ethanol, or a mixture comprising rapeseed oil, octanol and isopropanol, or else a silicone oil and a fatty ester but also a mixture of two organic solvents such as a mixture of octanol and ethanol.
  • the content by weight of the compound of formula (I) is between 0.1% and 10%, preferably between 1% and 5%, by weight relative to the weight of the organic liquid or mixture of organic liquids.
  • the present invention also relates to a process for preparing an organogel or oleogel comprising a step of bringing a compound of formula (I) into contact with an organic liquid or mixture of organic liquids, said liquid being chosen from organic solvents and oils, and being as defined above, said compound of formula (I) corresponding to the following formula: in which :
  • Sacc represents a monosaccharide or polysaccharide comprising up to 20 sugar units, in pyranose and/or furanose form and of the L and/or D series, said mono- or polysaccharide having at least one free hydroxyl function;
  • - Xi + represents a cation chosen from the group consisting of: Na + , Li + , K + , + NR 3 R 4 R 5 R 6 , R 7 -NH 3 + , + PR 3 R 4 R 5 R 6 and + SR 3 R 4 R 5 ,
  • R 3 , R 4 , R 5 and R 6 identical or different, representing a (Ci-Csojalkyl) group, optionally including at least one unsaturation, said alkyl group being optionally substituted by at least one (Ce-Cio)aryl group, in particular a phenyl group,
  • R 7 representing a (Ci-Csojalkyl) group, optionally including at least one unsaturation, said alkyl group being optionally substituted by at least one (Ce-Cio)aryl group, in particular a phenyl group,
  • R 2 represents H, methyl, or a (Ci-Csojalkyl) group optionally including at least one unsaturation, said alkyl group being optionally substituted by at least one (Ce-Cio)aryl group, in particular a phenyl group, as well as its tautomeric forms.
  • organogel denotes a gel of an organic solvent and the term oleogel denotes a gelled oil.
  • the method of the invention comprises the addition of an aqueous solution of the compound of formula (I) in the organic liquid or mixture of organic liquids.
  • the addition step further comprises a step of ultrasound treatment or a step of heating or cooling the organic liquid or mixture of organic liquids.
  • the organic liquid or mixture of organic liquids comprises an additional compound chosen from dyes or pigments, an opacifier, an organic or mineral UV filter, odorous molecules and active pharmaceutical ingredients, such as Nile red, carmine red, metal oxides, ethylhexyl triazone, eucalyptol or doxorubicin.
  • Example 1 Determination of the correct dosage for the formation of gels at 2% (w/v)
  • Example 2 Formation of a gel by adding a solvent + water mixture to the glycobarbiturate powder
  • Example 3 Formation of a gel by adding a concentrated solution of sodium glucosylbarbiturate to the solvent
  • the solvent is placed in a container with stirring then the aqueous solution of sodium glucosylbarbiturate (1.47 M) is added in the proportions defined above in example 1.
  • the mixture is left to stir for a few seconds then the stirring is stopped to allow the gel to form.
  • 80 ⁇ l of the aqueous solution of sodium glucosylbarbiturate (1.47 M) were added to 1 mL of 96% ethanol.
  • Example 4 Formation of a gel with apolar oils or solvents (examples: rapeseed oil, toluene, anisole, etc.)

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Organic Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Dispersion Chemistry (AREA)
  • Birds (AREA)
  • Dermatology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Saccharide Compounds (AREA)
  • Cosmetics (AREA)
  • Medicinal Preparation (AREA)
EP23701452.7A 2022-01-21 2023-01-20 Glycosylbarbiturat-geliermittel Pending EP4466094A1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR2200507A FR3132100B1 (fr) 2022-01-21 2022-01-21 Gélifiants à base de glycosylbarbiturates
PCT/EP2023/051377 WO2023139217A1 (fr) 2022-01-21 2023-01-20 Gélifiants à base de glycosylbarbiturates

Publications (1)

Publication Number Publication Date
EP4466094A1 true EP4466094A1 (de) 2024-11-27

Family

ID=81325005

Family Applications (1)

Application Number Title Priority Date Filing Date
EP23701452.7A Pending EP4466094A1 (de) 2022-01-21 2023-01-20 Glycosylbarbiturat-geliermittel

Country Status (7)

Country Link
US (1) US20250108116A1 (de)
EP (1) EP4466094A1 (de)
JP (1) JP2025502441A (de)
KR (1) KR20240140110A (de)
CN (1) CN118647450A (de)
FR (1) FR3132100B1 (de)
WO (1) WO2023139217A1 (de)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2899463B1 (fr) * 2006-04-07 2008-05-30 Oreal Utilisation dej compose c-glycoside comme agent activateur et regulateur de l'immunite cutanee

Also Published As

Publication number Publication date
FR3132100A1 (fr) 2023-07-28
WO2023139217A1 (fr) 2023-07-27
JP2025502441A (ja) 2025-01-24
CN118647450A (zh) 2024-09-13
KR20240140110A (ko) 2024-09-24
US20250108116A1 (en) 2025-04-03
FR3132100B1 (fr) 2025-05-02

Similar Documents

Publication Publication Date Title
EP0939670B1 (de) Neuartige zusammensetzungen auf basis von alkylglykosiden und fettalkoholen
KR102073769B1 (ko) 신규 당유도체 겔화제
EP0399909B1 (de) Kosmetische Zubereitung gegen das Altern der Haut
FR2734496A1 (fr) Composition emulsionnante a base d'alkylpolyglycosides, et ses utilisations
JP2014140383A (ja) 高純度酸型ソホロリピッド含有物及びその製造方法
EP0566438A1 (de) Verfahren zur Herstellung von D-Maltose-Monoestern mit einem hohen Gehalt von 6-0'-Ester und ihre Verwendung in Kosmetika, Zahnpflegemitteln, Pharmazeutik und Lebensmitteln
WO2023139217A1 (fr) Gélifiants à base de glycosylbarbiturates
Kajiki et al. Development of novel low-molecular-mass oil-gelling agents: Synthesis and physical properties of 1, 5-anhydro-D-glucitol and 1, 5-anhydro-D-mannitol protected with saturated linear fatty acids
EP1257351B1 (de) Neue familie von zusammensetzungen aus alkylpolyglykosiden und dimerdiolen, insbesondere verwendbar für die herstellung von versprühbaren öl-in-wasser emulsionen
CA2173815C (fr) Utilisation d'un compose hydrofluorocarbone dans une emulsion, emulsion et composition comprenant un tel compose
EP3595625B1 (de) Konzentrat mit mindestens einem mannosyleroythritollipid und mindestens einem polyglycerol- und fettsäureester
EP2350108B1 (de) C-glycosidverbindungen und verfahren zur herstellung von c-glycosidverbindungen
EP4605092A1 (de) Öl-in-wasser-emulsion mit einem emulgatorsystem aus einem cyclodextrin und einem emulgator stärkeursprung
WO1997047658A1 (fr) Association d'un monomere, oligomere, polymere comprenant au moins un groupe hydroxyle, avec un compose amphiphile complexant
FR3141855A1 (fr) Composition de soin de matières kératineuses
Afach et al. Lipase-catalyzed synthesis of d-psicose fatty acid diesters and their emulsification activities
EP0925781A1 (de) Hautdepigmentierungsmittel
EP0699433A2 (de) Kosmetische oder pharmazeutische Zusammensetzung, die Chitosanderivate enthalten
WO1999015147A2 (fr) Utilisation d'alkyl monoglucosides en tant que vecteurs moleculaires
FR3157149A1 (fr) Composition aqueuse à base d’une sennoside et d’alcool carbonylé
FR2736639A1 (fr) Nouveaux composes hydrofluorocarbones a fonction thioester, procede de preparation, utilisations et compositions les comprenant
BR102023026542A2 (pt) Síntese enzimática de um oleogelificante, oleogelificante assim obtido e uso
FR3152987A3 (fr) procédé pour les soins de la peau
FR3157203A1 (fr) Composition à base de robinine, de solvants hydrophiles et d’eau
FR3138038A1 (fr) Composition comprenant du glycolipide et un dérivé d'acide citrique

Legal Events

Date Code Title Description
STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: UNKNOWN

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE INTERNATIONAL PUBLICATION HAS BEEN MADE

PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: REQUEST FOR EXAMINATION WAS MADE

17P Request for examination filed

Effective date: 20240723

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC ME MK MT NL NO PL PT RO RS SE SI SK SM TR

DAV Request for validation of the european patent (deleted)
DAX Request for extension of the european patent (deleted)