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WO2022128470A1 - Procédé de réglage de la teneur en nicotine d'un aérosol de cigarette électronique - Google Patents

Procédé de réglage de la teneur en nicotine d'un aérosol de cigarette électronique Download PDF

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Publication number
WO2022128470A1
WO2022128470A1 PCT/EP2021/083732 EP2021083732W WO2022128470A1 WO 2022128470 A1 WO2022128470 A1 WO 2022128470A1 EP 2021083732 W EP2021083732 W EP 2021083732W WO 2022128470 A1 WO2022128470 A1 WO 2022128470A1
Authority
WO
WIPO (PCT)
Prior art keywords
nicotine
liquid
aerosol
precursor substance
inhaler
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.)
Ceased
Application number
PCT/EP2021/083732
Other languages
German (de)
English (en)
Inventor
Alp OHRI
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.)
Koerber Technologies GmbH
Original Assignee
Hauni Maschinenbau GmbH
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 Hauni Maschinenbau GmbH filed Critical Hauni Maschinenbau GmbH
Priority to EP21830617.3A priority Critical patent/EP4262445B1/fr
Priority to CN202180084642.2A priority patent/CN116600663A/zh
Priority to US18/257,735 priority patent/US20240130416A1/en
Publication of WO2022128470A1 publication Critical patent/WO2022128470A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/10—Chemical features of tobacco products or tobacco substitutes
    • A24B15/16—Chemical features of tobacco products or tobacco substitutes of tobacco substitutes
    • A24B15/167—Chemical features of tobacco products or tobacco substitutes of tobacco substitutes in liquid or vaporisable form, e.g. liquid compositions for electronic cigarettes
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/18—Treatment of tobacco products or tobacco substitutes
    • A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
    • A24B15/281—Treatment of tobacco products or tobacco substitutes by chemical substances the action of the chemical substances being delayed
    • A24B15/283—Treatment of tobacco products or tobacco substitutes by chemical substances the action of the chemical substances being delayed by encapsulation of the chemical substances
    • A24B15/284—Treatment of tobacco products or tobacco substitutes by chemical substances the action of the chemical substances being delayed by encapsulation of the chemical substances the additive being bound to a host by chemical, electrical or like forces, e.g. use of precursors, inclusion complexes
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/18—Treatment of tobacco products or tobacco substitutes
    • A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
    • A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
    • A24B15/36—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring
    • A24B15/38—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only nitrogen as hetero atom
    • A24B15/385—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only nitrogen as hetero atom in a five-membered ring
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24F—SMOKERS' REQUISITES; MATCH BOXES; SIMULATED SMOKING DEVICES
    • A24F40/00—Electrically operated smoking devices; Component parts thereof; Manufacture thereof; Maintenance or testing thereof; Charging means specially adapted therefor
    • A24F40/30—Devices using two or more structurally separated inhalable precursors, e.g. using two liquid precursors in two cartridges
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24F—SMOKERS' REQUISITES; MATCH BOXES; SIMULATED SMOKING DEVICES
    • A24F40/00—Electrically operated smoking devices; Component parts thereof; Manufacture thereof; Maintenance or testing thereof; Charging means specially adapted therefor
    • A24F40/10—Devices using liquid inhalable precursors
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24F—SMOKERS' REQUISITES; MATCH BOXES; SIMULATED SMOKING DEVICES
    • A24F40/00—Electrically operated smoking devices; Component parts thereof; Manufacture thereof; Maintenance or testing thereof; Charging means specially adapted therefor
    • A24F40/40—Constructional details, e.g. connection of cartridges and battery parts

Definitions

  • the present invention relates to a method for adjusting the nicotine content of an aerosol in an inhaler, comprising the following steps:
  • a feeding step in which at least one liquid with a first nicotine content is fed from a vaporizer tank to an electric vaporizer
  • a delivery step in which a final aerosol, which consists of the combination of all aerosols formed in the inhaler from the at least one liquid, is delivered from the inhaler to a user.
  • Inhalers in particular in the form of electronic cigarettes (hereinafter referred to as e-cigarettes) are used in the medical field and in particular in the luxury goods industry. E-cigarettes are very popular and are increasingly replacing the consumption of conventional tobacco products. Unlike conventional tobacco products, where the smoke of burning plant parts, especially tobacco, is inhaled by the consumer, no plant parts are burned in e-cigarettes. Instead, a liquid, usually referred to as liquid, is vaporized in a vaporizer unit and mixed with air in a flow channel, creating an aerosol, mist, or aerosol-vapor mixture that the consumer inhales.
  • liquid usually referred to as liquid
  • the liquid is stored on or in the vaporizer cartridge. Different mixtures with different components of the same or different vapor densities are used as liquids.
  • a typical mixture for use in an e-cigarette has e.g. components of glycerin and propylene glycol, enriched with nicotine, optionally with almost any flavoring.
  • the nicotine content for the cigarette has a maximum value, for the nicotine content of an e-cigarette there are maximum values for nicotine in the liquid that must not be exceeded.
  • the nicotine content of e-cigarette liquids is limited to a concentration of 20 mg/ml. This limitation is only valid for liquids according to 2014/40/EU.
  • the nicotine concentration of the aerosols produced during vaporization is not limited.
  • e-cigarette cartridges are sold that are filled with liquids containing 5% nicotine.
  • the popularity and the pleasant and, above all, tobacco cigarette-like experience felt by e-cigarette smokers are not only due to the nicotine salts in the liquids sold in the USA, but also to the high concentration, because this allows a rapid blood nicotine concentration increase comparable to tobacco cigarettes. It is desirable to achieve a similar blood nicotine concentration with e-cigarette liquids that comply with the regulations in the EU.
  • the object of the present invention is therefore to provide a method that enables an increased blood nicotine concentration compared to that which can be achieved with conventional liquids and at the same time satisfies the provisions of 2014/40/EU.
  • At least one of the at least one liquid has a precursor substance that can be converted into nicotine by a chemical reaction
  • the method also includes a nicotine production step in which the precursor Substance is converted into nicotine by chemical reaction, so that the final aerosol has a second nicotine content that is higher than the first nicotine content.
  • the nicotine content in the aerosol produced by adding at least one substance to the liquid which only converts to nicotine during the formation of the aerosol.
  • the nicotine content of the liquid can be kept within the statutory limits, while at the same time the aerosol inhaled by the consumer has the higher nicotine content desired by the consumer.
  • the precursor substance is converted during the process and continues to reach the consumer in the aerosol as nicotine.
  • aerosol refers to the vapor phase that is produced by evaporation of the liquid, and is also intended to mean mist, vapor or Mixtures of aerosol, mist and/or vapour, ie the gaseous phase may contain solid and/or liquid particles.
  • Any chemical reaction is conceivable as a chemical reaction by which the precursor substance is converted into nicotine, substitutions, additions, eliminations, rearrangements, radical reactions or acid-base reactions.
  • the chemical reaction is particularly preferably an oxidation or, in particular, a reduction.
  • a chemical reduction is the reverse reaction of an oxidation, in which a reducing agent donates electrons to (thereby "reducing") an already oxidized substance.
  • the conversion of the precursor substance into nicotine occurs using a catalyst.
  • a catalyst enables reactions that would not be possible or only uneconomically possible without the catalyst, since z. B. too much energy would have to be supplied to initiate and / or carry out the reaction.
  • the catalyst lowers the required activation energy to a certain extent. The reaction is therefore more economical or even possible at all, because without the reduction other competing reactions would take place which would not allow the actually desired reaction or only with a very low yield.
  • the precursor substance is converted into nicotine using an enzyme.
  • Enzymes are proteins that typically selectively catalyze a specific reaction. Also enzymes can allow the conversion reaction of the precursor substance to nicotine to proceed under mild conditions
  • Nicotine has the following structural formula: Various compounds are conceivable as a precursor substance.
  • nicotine glucuronide or nornicotine can be used as a precursor substance.
  • the former can be converted into nicotine by means of ß-glucurodnidase, in particular immobilized on a filter or a column, and the latter by reaction with methyltransferase. This is where enzymes come into play.
  • the precursor substance is very particularly preferably cotinine or nicotine N'-oxide. Both compounds can be converted into nicotine in a reduction reaction.
  • Cotinine occurs as an alkaloid in tobacco plants.
  • the structural formulas of cotinine and nicotine N'-oxide are shown below:
  • the reduction of cotinine or nicotine N'-oxide is preferably carried out by catalytic hydrogenation, using lithium alanate (UAIH4) in polar protic solvents or using other zinc hydride complexes. In this way, the reduction can be accomplished under mild conditions.
  • UAIH4 lithium alanate
  • the precursor substance is preferably present in an amount such that a nicotine content of at least 30 mg/ml, preferably in particular at least 40 mg/ml and particularly preferably at least 50 mg/ml, is achieved in the aerosol.
  • liquids that do not contain any nicotine but only precursor substances so that all the nicotine is only present in the aerosol.
  • the reactant can be present as a liquid in the liquid.
  • the reactant can be a solid. It can either be present as a solid or it can be converted into a solid by means of freeze drying.
  • the reactant is provided in a contact element, and in the nicotine generation step the precursor substance is brought into contact with the reactant in the contact element.
  • Filters in particular can be used as such a contact element, as can lattice structures. These are inserted into the air duct of an e-cigarette and, thanks to their large surface area, ensure intensive contact between the aerosol and, in particular, the precursor substance contained in it, with the reactant contained in the filter.
  • a preferred embodiment consists in the application of nanoparticles or microparticles in order to achieve the largest possible surface area.
  • a preferred embodiment is the use of a spray system to load the aerosol with the respective liquid reactant.
  • An alternative preferred embodiment uses a filter and a semi-permeable membrane that allows the reactant to escape into the aerosol channel while preventing the aerosol from entering the filter.
  • a pad soaked with the liquid reactant can be attached in the air duct.
  • the aerosol channel can be completely or partially covered with the pad, with any geometries being able to be used for the pad.
  • a sieve or grid may be employed to wick/receive the liquid reactant. The screen or grid is penetrated by the aerosol. In this way, the precursor substance to be converted is converted, the increased surface area enabling particularly intensive contact of the reactant with the aerosol.
  • the attachments described above in the form of pads, grids or filters are so-called "disposables", ie consumables that would have to be disposed of and replaced after a number of puffs, because e.g. B. in the case of reducing agents, the redox potential is no longer given after a certain time of moves.
  • the number of puffs is preferably recorded digitally and integrated into an app for controlling the e-cigarette. In this way, the consumer is reminded or made aware of how many puffs are still available and when the filter needs to be changed.
  • the nicotine generation step can occur before the vaporization step, after the vaporization step, or simultaneously with the vaporization step.
  • the nicotine precursor can therefore first be converted to nicotine and then be transferred to the aerosol phase together with the remaining liquid. Alternatively, the reaction occurs during formation of the aerosol.
  • the conversion of the precursor substance into nicotine particularly preferably takes place in the aerosol phase.
  • the method is carried out in an inhaler with an evaporator tank with at least two evaporator tank chambers, it being possible for each evaporator tank chamber to be assigned its own evaporator. In this way it is possible to transfer different liquids with different ingredients separately into the aerosol phase.
  • a first liquid can contain nicotine and the precursor substance can be contained either in the first liquid or in a second liquid.
  • the precursor substance is particularly preferably contained in a second liquid.
  • At least two liquids are used, with a first liquid containing nicotine and a further liquid containing a reactant which causes the precursor substance to be converted into nicotine.
  • the first liquid can contain nicotine and the precursor substance, with the precursor substance only reacting with the reactant when the two liquids come together.
  • the liquid containing nicotine and the precursor substance and the liquid containing the reactant are transferred separately into the aerosol phase.
  • the reaction of the precursor substance with the reactant to form nicotine then takes place in the aerosol phase when the two aerosols, ie the aerosols from the first and further liquid, are combined with one another.
  • the precursor substance can react with the reactant to form nicotine.
  • the result is the final aerosol that has the second nicotine level that is higher than the first nicotine level.
  • the second liquid therefore particularly preferably contains both the precursor substance and the reactant.
  • the reactant can also be provided in the form of a filter in the air duct for the second aerosol and convert the precursor substance as it passes through the filter in the aerosol.
  • the liquid containing nicotine and the liquid containing the precursor substance and optionally the reactant are transferred separately into the aerosol phase.
  • the reaction of the precursor substance with the reactant to form nicotine therefore takes place separately. Only after the precursor substance has been converted into nicotine is the aerosol containing the newly generated nicotine combined with the aerosol of the liquid, which already contained nicotine at the beginning.
  • a three tank system is used.
  • the various substances can be stored separately from one another.
  • a first tank would contain a conventional liquid with the basic nicotine content. This nicotine level would preferably correspond to the maximum allowable nicotine level.
  • Another tank contains a liquid containing the precursor substance.
  • a liquid is contained in a third tank, which contains the reactant and, if desired and/or necessary, a carrier substance.
  • the usual carrier substances such as water, propylene glycol (PG) and/or glycerine, in particular vegetable glycerine ("vegan glycerol" - VG) are particularly suitable as carrier substances.
  • the various liquids are formed into aerosols.
  • the precursor substance is first reacted separately with the reactant to form nicotine. This prevents other components of the liquid from reacting with the reactant in an uncontrolled manner. For example, cotinine can first be reduced separately to nicotine, and it is avoided that other components of the liquid such as e.g. B. Flavors are also reduced in an undesirable side reaction.
  • a multi-chamber system preferably also has a number of separate evaporators.
  • the aerosols are then mixed together, creating the final aerosol with an increased nicotine content, which is then inhaled by the consumer.
  • the precursor substance is converted into nicotine before and/or between two e-cigarette sessions.
  • the necessary amount of precursor substance is converted, stored and/or kept in the aerosol phase by means of heat supply until the consumer starts the next session. In this way, reactions that require more time and energy to take place and deliver enough nicotine molecules can also be used. If the next session is not undertaken in a longer period of time, the heating is stopped so that no unintended reactions take place as time elapses.
  • FIG. 1 shows a schematic representation to illustrate the steps of a first variant of the method according to the invention
  • 3a and 3b show a schematic representation of the arrangement of a pad with reactant for carrying out the present invention
  • Figures 4a and 4b are schematic representations of the arrangement of a grid for containing reactant for the practice of the present invention.
  • the first evaporator 1 shows a first evaporator 1 connected to a first tank 2a and a second tank 2b.
  • the first tank 2a contains a conventional liquid for an e-cigarette with a first nicotine content that corresponds to the permissible nicotine content of 20 mg/ml and with a cotinine content.
  • the second tank 2b there is a second liquid which contains a reducing agent in addition to a carrier.
  • the two liquids are vaporized with aerosol formation.
  • the result is the final aerosol 4, which has a second nicotine content that is higher than the first nicotine content.
  • the second tank 2 shows an embodiment with three different tanks 2a, 2b, 2c, each of which is assigned an evaporator 1a, 1b, 1c.
  • the first tank 2a contains a conventional liquid with the base nicotine content, which corresponds to the maximum permissible nicotine content of a liquid.
  • a second tank 2b contains a second liquid containing cotinine.
  • the third tank 2c contains a third liquid, which contains the reducing agent and PG as a carrier substance.
  • a first step the various liquids are formed into aerosols.
  • the second aerosol 3b and the third aerosol 3c are mixed, and the cotinine contained in the second aerosol 3b is reduced to nicotine with the reducing agent contained in the third aerosol 3c.
  • the second and third aerosols 3b, 3c are still separated from the first aerosol 3a. In this way it is avoided that other components of the liquid such as e.g. B. Flavors that are contained together with the nicotine in the first aerosol 3a react with the reactant and are also reduced in an undesirable side reaction.
  • the aerosols are then mixed together, and the final aerosol 4 with an increased nicotine content is created, which is finally inhaled by the consumer.
  • FIG. 3a shows an embodiment of an air channel 5 of an inhaler for carrying out the method according to the invention in a side view
  • FIG. 3b shows the same air channel 5 in a plan view
  • a filter 6 containing the nanoparticulate reducing agent is arranged in the air duct 5 .
  • the aerosol 3b containing cotinine passes through the filter 6 and thereby comes into contact with the reducing agent, so that the cotinine contained in the aerosol 3b is reduced to nicotine.
  • FIG. 4a shows a further embodiment of an air channel 5 of an inhaler for carrying out the method according to the invention in a side view
  • FIG. 4b shows the same air channel 5 in a plan view.
  • a screen or grid 7 is arranged, in which the liquid reducing agent is received.
  • This sieve 7 is penetrated by the aerosol 3b, as a result of which the cotinine contained to be reduced can be comprehensively reduced due to the enlarged surface and further reaches the consumer as nicotine in the aerosol 3b.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Procédé de réglage de la teneur en nicotine d'un aérosol dans un inhalateur, comprenant les étapes suivantes : - une étape d'alimentation, dans laquelle au moins un liquide ayant une première teneur en nicotine est amené d'un réservoir de vaporisation à un vaporisateur électrique, - une étape de vaporisation, dans laquelle ledit liquide est vaporisé, produisant un aérosol, - une étape d'évacuation, dans laquelle un aérosol final, constitué par la fusion de tous les aérosols formés dans l'inhalateur à partir dudit liquide, est évacué de l'inhalateur vers un utilisateur, au moins l'un des liquides ayant une substance précurseur, qui peut être convertie en nicotine par réaction chimique, et le procédé comprenant en outre une étape de production de nicotine, dans laquelle la substance précurseur est convertie en nicotine par réaction chimique de telle sorte que l'aérosol final a une seconde teneur en nicotine qui est supérieure à la première teneur en nicotine, permet d'obtenir une concentration de nicotine dans le sang accrue par rapport à la concentration de nicotine lors de l'utilisation de liquides classiques, et se faisant est en même temps conforme aux dispositions de 2014/40/EU.
PCT/EP2021/083732 2020-12-16 2021-12-01 Procédé de réglage de la teneur en nicotine d'un aérosol de cigarette électronique Ceased WO2022128470A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP21830617.3A EP4262445B1 (fr) 2020-12-16 2021-12-01 Procédé de réglage de la teneur en nicotine d'un aérosol de cigarette électronique
CN202180084642.2A CN116600663A (zh) 2020-12-16 2021-12-01 调节电子烟气溶胶中的尼古丁含量的方法
US18/257,735 US20240130416A1 (en) 2020-12-16 2021-12-01 Method for adjusting the nicotine content in an e-cigarette aerosol

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102020133733.7A DE102020133733B4 (de) 2020-12-16 2020-12-16 Verfahren zur Einstellung des Nikotingehalts in einem E-Zigaretten-Aerosol
DE102020133733.7 2020-12-16

Publications (1)

Publication Number Publication Date
WO2022128470A1 true WO2022128470A1 (fr) 2022-06-23

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PCT/EP2021/083732 Ceased WO2022128470A1 (fr) 2020-12-16 2021-12-01 Procédé de réglage de la teneur en nicotine d'un aérosol de cigarette électronique

Country Status (5)

Country Link
US (1) US20240130416A1 (fr)
EP (1) EP4262445B1 (fr)
CN (1) CN116600663A (fr)
DE (1) DE102020133733B4 (fr)
WO (1) WO2022128470A1 (fr)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20150344456A1 (en) * 2014-05-27 2015-12-03 R.J. Reynolds Tobacco Company Nicotine salts, co-crystals, and salt co-crystal complexes
US20170112182A1 (en) * 2015-10-23 2017-04-27 Next Generation Labs, LLC Nicotine composition for vaping devices and vaping devices employing the same

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10172388B2 (en) 2015-03-10 2019-01-08 Rai Strategic Holdings, Inc. Aerosol delivery device with microfluidic delivery component

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20150344456A1 (en) * 2014-05-27 2015-12-03 R.J. Reynolds Tobacco Company Nicotine salts, co-crystals, and salt co-crystal complexes
US20170112182A1 (en) * 2015-10-23 2017-04-27 Next Generation Labs, LLC Nicotine composition for vaping devices and vaping devices employing the same

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
HARVANKO ARIT M ET AL: "Characterization of Nicotine Salts in 23 Electronic Cigarette Refill Liquids", NICOTINE & TOBACCO RESEARCH, vol. 22, no. 7, 12 June 2020 (2020-06-12), pages 1239 - 1243, XP055899577, Retrieved from the Internet <URL:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7291795/pdf/ntz232.pdf> [retrieved on 20220309], DOI: 10.1093/ntr/ntz232 *
MALLOCK NADJA ET AL: "Trendy e-cigarettes enter Europe: chemical characterization of JUUL pods and its aerosols", ARCHIVES OF TOXICOLOGY, SPRINGER, DE, vol. 94, no. 6, 18 March 2020 (2020-03-18), pages 1985 - 1994, XP037168473, ISSN: 0340-5761, [retrieved on 20200318], DOI: 10.1007/S00204-020-02716-3 *

Also Published As

Publication number Publication date
CN116600663A (zh) 2023-08-15
DE102020133733A1 (de) 2022-06-23
DE102020133733B4 (de) 2022-07-07
US20240130416A1 (en) 2024-04-25
EP4262445B1 (fr) 2025-02-05
EP4262445A1 (fr) 2023-10-25

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