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WO2017081480A1 - Formulation liquide - Google Patents

Formulation liquide Download PDF

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Publication number
WO2017081480A1
WO2017081480A1 PCT/GB2016/053547 GB2016053547W WO2017081480A1 WO 2017081480 A1 WO2017081480 A1 WO 2017081480A1 GB 2016053547 W GB2016053547 W GB 2016053547W WO 2017081480 A1 WO2017081480 A1 WO 2017081480A1
Authority
WO
WIPO (PCT)
Prior art keywords
electronic cigarette
stabiliser
liquid formulation
formulation according
cigarette liquid
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/GB2016/053547
Other languages
English (en)
Inventor
John TILEY
Michael PACEY
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.)
JAYTEE BIOSCIENCES Ltd
Original Assignee
JAYTEE BIOSCIENCES Ltd
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 JAYTEE BIOSCIENCES Ltd filed Critical JAYTEE BIOSCIENCES Ltd
Priority to US15/775,995 priority Critical patent/US20180325164A1/en
Priority to CA3005301A priority patent/CA3005301A1/fr
Priority to EP16813111.8A priority patent/EP3373974A1/fr
Publication of WO2017081480A1 publication Critical patent/WO2017081480A1/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
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
    • A61K31/05—Phenols
    • 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
    • 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
    • A24B15/302—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances by natural substances obtained from animals or plants
    • 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
    • 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
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • 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
    • A61K31/465—Nicotine; Derivatives thereof
    • 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
    • A61K31/658—Medicinal preparations containing organic active ingredients o-phenolic cannabinoids, e.g. cannabidiol, cannabigerolic acid, cannabichromene or tetrahydrocannabinol
    • 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
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
    • 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
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
    • 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
    • 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
    • A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin
    • 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
    • A61K9/08—Solutions
    • 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

Definitions

  • the present invention relates to liquid formulations and in particular to liquid formulations containing cannabidiol. It also relates to e-cigarette liquids (vaping liquids or vaping formulations) containing cannabidiol.
  • E-cigarette liquids or formulations typically include nicotine in a liquid carrier comprising principally propylene glycol. However, it is proposed to replace some or all of the nicotine with cannabidiol.
  • Cannabidiol (2-[(l , 6R)-6-isopropenyl-3-methylcyclohex-2-en-lyl]-5-pentylbenzene-l,3-diol) is one of at least 85 active cannabinoids found in cannabis.
  • Cannabidiol (hereinafter referred to as "CBD") is considered to be a safer alternative to tetrahydrocannabinol (THC) as it produces less or no short term memory impairment in subjects. It is also considered not to generate the feelings of anxiety often associated with the use of THC.
  • CBD The structure of CBD is as follows:
  • the two hydroxyl groups on the benzene ring may be readily oxidised. It has been found that formulations of CBD in a liquid carrier comprising propylene glycol result in the discolouration of the liquid. Without wishing to be bound by theory, this is believed to be a result of the oxidation of at least one of the hydroxyl groups of the CBD molecule, likely by the propylene glycol component.
  • an electronic cigarette liquid formulation comprising cannabidiol, a stabiliser and a liquid carrier; wherein the liquid carrier comprises 60-100% v/v propylene glycol, 0-40% v/v glycerol, and 0-40% v/v of one or more triglyceride compounds; and the stabiliser comprises a head portion and a tail portion, wherein the head portion includes one or more reducing moieties and the tail portion comprises a C3-C20 straight or branched aliphatic chain, wherein the stabiliser is soluble or miscible with the liquid carrier.
  • Electronic cigarette liquid formulations may also be referred to as an e-cigarette liquid or simply an e-liquid. They are also sometime referred to as vaping liquids or vaping formulations.
  • the major component of the liquid carrier is propylene glycol, which comprises at least 60% by volume of the liquid carrier.
  • the liquid carrier may also contain glycerol and/or one or more triglyceride compounds.
  • triglyceride compounds tend to be derived from natural sources, they are typically provided in the form of a mixture of compounds.
  • Further liquid components may be included in the liquid carrier.
  • the head portion of the stabiliser is typically a stronger reducing agent than CBD and thus is preferentially oxidised. The head portion of the stabiliser therefore acts as an anti-oxidant for the CBD formulation.
  • the tail portion of the stabiliser is required to ensure that the stabiliser is soluble or miscible in the formulation.
  • the aliphatic group may be a branched or straight chain alkyl (alkane) group, a branched or straight chain alkene group or a branched or straight chain alkyne group. In embodiments in which the aliphatic chain is unsaturated, it may be mono unsaturated or polyunsaturated.
  • the head portion of the stabiliser may be a hydroxyl substituted 5- or 6-membered carbocyclic or heterocyclic ring. In embodiments in which the ring is a heterocyclic ring, it may contain one or more heteroatoms each independently selected from oxygen, nitrogen and sulphur. Suitably, the heteroatom is an oxygen atom. Examples of suitable head portions include:
  • Ascorbic acid derivatives such as:
  • R 1 is a C3-C20 aliphatic tail portion, optionally coupled to the head portion via a linker moiety.
  • Hydroquinone derivatives such as:
  • R 2 and R 3 are each independently selected from H, a C1-C6 alkyl group and a C3-C20 aliphatic tail portion optionally coupled to the head portion via a linker moiety, provided that at least one of R 2 and R 3 comprises an aliphatic tail portion.
  • Hydroxychromane derivatives such as:
  • R 4 , R 5 , R 6 and R 7 are each independently selected from OH, H, and a C1-C3 alkyl group, wherein at least one of R 4 , R 5 , R 6 and R 7 is OH; and R 8 is a C3-C20 aliphatic tail portion, optionally coupled to the head portion via a linker moiety.
  • Hydroxyanisole derivatives such as:
  • R 9 and R 10 are each independently selected from H, a C1-C6 alkyl group and a C3-C20 aliphatic tail portion, optionally coupled to the head portion via a linker moiety, provided that at least one of R 9 and R 10 comprises an aliphatic tail portion.
  • Hydroxytoluene derivatives such as:
  • R 11 and R 12 are each independently selected from H, a C1-C6 alkyl group and a C3-C20 aliphatic tail portion, optionally coupled to the head portion via a linker moiety, provided that at least one of R 11 and R 12 comprises an aliphatic tail portion.
  • Gallic acid derivatives such as:
  • R 13 is a C3-C20 aliphatic tail portion.
  • the linker group where present, may be selected from -0-, -0(0)C-, - C(O)-, -N(H)C(0)- and -N(H)-.
  • the aliphatic tail portion is suitably a branched or straight chain alkyl group containing 3 to 20, suitably 6 to 20, 7 to 20, 10 to 20 or 12 to 18 carbon atoms.
  • a suitable stabiliser comprises an ascorbic acid derivative as shown above, wherein Rl is a C6-C20 straight or branched aliphatic chain connected to the ascorbic acid head group via a -C(O)- linker group:
  • R 14 is a C3-C20 aliphatic tail portion.
  • R 14 may be a C3-C20 branched or straight chain alkyl group, such as for example a C6-C20 alkyl group, a C10-C20 alkyl group or a C12-C20 alkyl group.
  • the stabiliser may be an ascorbate ester of a long chain fatty acid having from 6 to 20 carbon atoms, 7 to 20 carbon atoms, 8 to 18 carbon atoms or 10 to 16 carbon atoms.
  • the long chain fatty acid may be unsaturated, monounsaturated or polyunsaturated.
  • the stabiliser may be an ascorbyl ester of palmitic acid, which has a chain comprising 16 carbon atoms.
  • the formulation is intended for human consumption, suitably in the form of an e-cigarette formulation, the stabiliser may already be approved for human consumption and/or as an approved food additive. For example, it may already have an "E" number.
  • ascorbyl palmitate which is also known as E304 and is approved in the EU, the US, Australia and New Zealand.
  • R 4 and R 6 are each independently H or CH 3 ;
  • R 5 is OH;
  • R 7 is CH 3 ; and
  • R 8 is a Ci 6 branched chain alkyl group;
  • R 13 is a propyl group
  • R 2 is a tertiary butyl group and R 3 is H;
  • R 11 and R 12 are each independently a tertiary butyl group.
  • the CBD may be present in the formulation in an amount of lOmg/ml to 300mg/ml.
  • the volume (ml) value refers to the volume of the liquid carrier.
  • the lower limit on the amount of CBD in the formulation may be 15mg/ml, 20mg/ml, 25mg/ml, 30mg/ml, 35mg/ml. 40mg/ml, 45mg/ml or 50mg/ml.
  • the upper limit on the amount of CBD present in the formulation may be 250mg/ml, 200mg/ml or 150mg/ml.
  • the amount of the stabiliser present in the formulation may be 0.5% to 5% by weight of the CBD content.
  • the stabiliser may be present in an amount of 0.5% to 2% by weight or 0.5 to 1.5% by weight of the CBD present in the formulation.
  • the ratio (weight/ml) of CBD to stabiliser in the formulation may be 200:1 to 50:1.
  • the stabiliser may be present in the formulation in an amount of 0.05mg/ml to 5mg/ml.
  • the volume (ml) refers to the volume of the liquid carrier.
  • the liquid carrier may include glycerol and/or one or more glyceride compounds, suitably one or more plant-derived glyceride compounds.
  • Glycerol and/or glyceride compounds are often present in E-cigarette liquid formulations and facilitate the formation of the vapour for inhalation when heated within the electronic cigarette.
  • the formulation may contain nicotine.
  • the CBD is intended to replace at least some of the nicotine. Accordingly, the formulation may contain less nicotine than would otherwise be present in an E-cigarette formulation.
  • Formulations according to the invention may be used to wean users away from nicotine.
  • a number of different formulations may be available which contain a decreasing amount of nicotine.
  • a first formulation which contains CBD and a first amount of nicotine
  • a second formulation which contains CBD and a second amount of nicotine, wherein the second amount of nicotine is less than the first amount of nicotine.
  • a third formulation may be provided, wherein the third formulation contains CBD and a third amount of nicotine, wherein the third amount of nicotine is less than the second amount of nicotine.
  • Such formulations may be available separately or they may form part of a kit.
  • a kit containing a first formulation which contains CBD and a first amount of nicotine and a second formulation which contains CBD and a second amount of nicotine, wherein the second amount of nicotine is less than the first amount of nicotine.
  • a kit which further includes a third formulation which contains CBD and a third amount of nicotine, wherein and the third amount of nicotine is less than the second amount of nicotine.
  • the formulations are as defined herein.
  • the formulations discussed above are suitably formulations as defined in the first aspect of the invention, which also include nicotine.
  • the first, second and optionally third formulations suitably comprise cannabidiol, nicotine, a stabiliser and a liquid carrier; wherein the liquid carrier comprises 60-100% v/v propylene glycol, 0-40% v/v glycerol, and 0-40% v/v of one or more triglyceride compounds; and the stabiliser comprises a head portion and a tail portion, wherein the head portion includes one or more reducing moieties and the tail portion comprises a C3-C20 straight or branched aliphatic chain, wherein the stabiliser is soluble or miscible with the liquid carrier.
  • the amount of nicotine in the first, second and third formulations decreases.
  • the amount of nicotine present in the formulations of the invention may be 0 to 50mg/ml. Thus, no nicotine may be present in the formulation or, where present, it may be present in an amount of for example 5 to 40mg/ml, such as 10 to 30mg/ml.
  • the formulation may further comprise a flavouring agent.
  • a flavouring agent is common in the field of E-cigarette liquid formulations.
  • the formulation may include a scent agent which releases a desired scent when the liquid is heated.
  • the flavouring component and/or the scent component may be considered to form a part of the liquid carrier.
  • the liquid carrier may further comprise 0-5% v/v of a liquid flavouring component and 0-5% v/v of a scent component.
  • the liquid carrier comprises 0-2% v/v of a liquid flavouring component and 0-2% v/v of a scent component.
  • the formulation is suitably substantially free from THC.
  • substantially free it is meant that the formulation suitably includes less than 0.1 wt% THC, suitably less than 0.01 wt% or less than 0.001 wt% THC.
  • substantially free means that THC is not detectable in the formulation by HPLC.
  • a further aspect of the invention provides a cartridge containing an electronic cigarette liquid formulation as defined hereinabove.
  • Such cartridges are suitably configured for location in an electronic cigarette.
  • a yet further aspect of the invention provides an electronic cigarette including an electronic cigarette liquid formulation as defined herein.
  • Comparative Example 1 A 20% w/v solution of CBD in propylene glycol with no stabiliser was prepared by dissolving 2g of CBD in 8ml of propylene glycol. The solution was placed in an open glass vial and monitored over a period of time. The colour of the solution was monitored during this time and the results are set out below:
  • the colouration of the solution was due to the presence of an oxidised species of the CBD, wherein the CBD was being oxidised by the propylene glycol carrier.
  • the oxidised species is thought to be a quinone derivative of CBD.
  • Example 1 A stabilised CBD solution was prepared by adding 0.2% w/v butylated hydroxyanisole (BHA) to the solution of Comparative Example 1 (2g CBD and 20mg BHA in 8ml propylene glycol). The solution was placed in an open glass vial and monitored over a period of time. The colour of the solution was monitored during this time and the results are set out below:
  • the rate of oxidation of the CBD in solution is significantly slowed by the addition of the BHA.
  • a stabilised CBD solution was prepared by adding 0.05% w/v 6-O-palmitoyl-L-ascorbic acid (6-0- AP) to the solution of Comparative Example 1 (2g CBD and 5mg 6-O-AP in 8ml propylene glycol). The solution was placed in an open glass vial and monitored over a period of time. The colour of the solution was monitored during this time and the results are set out below:
  • a stabilised CBD solution was prepared by adding 0.2% w/v 6-O-palmitoyl-L-ascorbic acid (6-O-AP) to the solution of Comparative Example 1 (2g CBD and 20mg 6-O-AP in 8ml propylene glycol). The solution was placed in an open glass vial and monitored over a period of time. The colour of the solution was monitored during this time and the results are set out below:
  • a stabilised CBD solution was prepared by adding 0.05% w/v 6-O-AP to the solution of
  • a stabiliser as defined herein can reduce, slow down or prevent the oxidation of a solution of CBD in propylene glycol.

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Abstract

La présente invention concerne une formulation liquide de cigarette électronique (e-liquide) comprenant du cannabidiol, un agent stabilisant et un transporteur liquide ; ledit transporteur liquide comprenant de 60 à 100 % en volume de propylène glycol, de 0 à 40 % en volume de glycérol, et de 0 à 40 % en volume d'un ou plusieurs composés triglycérides ; ledit agent stabilisant comprenant une partie tête et une partie queue, ladite partie tête comprenant une ou plusieurs fractions réductrices et ladite partie queue comprenant une chaîne aliphatique linéaire ou ramifiée en C3-C20, ledit agent stabilisant étant soluble dans le transporteur liquide ou miscible avec celui-ci.
PCT/GB2016/053547 2015-11-12 2016-11-11 Formulation liquide Ceased WO2017081480A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
US15/775,995 US20180325164A1 (en) 2015-11-12 2016-11-11 Liquid formulation
CA3005301A CA3005301A1 (fr) 2015-11-12 2016-11-11 Formulation liquide
EP16813111.8A EP3373974A1 (fr) 2015-11-12 2016-11-11 Formulation liquide

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB1520014.0 2015-11-12
GB1520014.0A GB2544468A (en) 2015-11-12 2015-11-12 Liquid formulation

Publications (1)

Publication Number Publication Date
WO2017081480A1 true WO2017081480A1 (fr) 2017-05-18

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Application Number Title Priority Date Filing Date
PCT/GB2016/053547 Ceased WO2017081480A1 (fr) 2015-11-12 2016-11-11 Formulation liquide

Country Status (5)

Country Link
US (1) US20180325164A1 (fr)
EP (1) EP3373974A1 (fr)
CA (1) CA3005301A1 (fr)
GB (1) GB2544468A (fr)
WO (1) WO2017081480A1 (fr)

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CN107343668A (zh) * 2017-08-31 2017-11-14 云南巴菰生物科技有限公司 一种提升香气质感的电子烟油及其制备方法与它的用途
CN108186566A (zh) * 2018-01-24 2018-06-22 云南汉木森生物科技有限责任公司 一种舒缓紧张、安神助眠的雾化剂及其制备方法
USD825102S1 (en) 2016-07-28 2018-08-07 Juul Labs, Inc. Vaporizer device with cartridge
US10045568B2 (en) 2013-12-23 2018-08-14 Juul Labs, Inc. Vaporization device systems and methods
US10045567B2 (en) 2013-12-23 2018-08-14 Juul Labs, Inc. Vaporization device systems and methods
US10058130B2 (en) 2013-12-23 2018-08-28 Juul Labs, Inc. Cartridge for use with a vaporizer device
US10076139B2 (en) 2013-12-23 2018-09-18 Juul Labs, Inc. Vaporizer apparatus
US10104915B2 (en) 2013-12-23 2018-10-23 Juul Labs, Inc. Securely attaching cartridges for vaporizer devices
US10111470B2 (en) 2013-12-23 2018-10-30 Juul Labs, Inc. Vaporizer apparatus
USD836541S1 (en) 2016-06-23 2018-12-25 Pax Labs, Inc. Charging device
USD842536S1 (en) 2016-07-28 2019-03-05 Juul Labs, Inc. Vaporizer cartridge
US10244793B2 (en) 2005-07-19 2019-04-02 Juul Labs, Inc. Devices for vaporization of a substance
US10279934B2 (en) 2013-03-15 2019-05-07 Juul Labs, Inc. Fillable vaporizer cartridge and method of filling
USD849996S1 (en) 2016-06-16 2019-05-28 Pax Labs, Inc. Vaporizer cartridge
USD851830S1 (en) 2016-06-23 2019-06-18 Pax Labs, Inc. Combined vaporizer tamp and pick tool
US10405582B2 (en) 2016-03-10 2019-09-10 Pax Labs, Inc. Vaporization device with lip sensing
WO2019211629A1 (fr) * 2018-05-03 2019-11-07 Nicoventures Trading Limited Formule vaporisable
US10512282B2 (en) 2014-12-05 2019-12-24 Juul Labs, Inc. Calibrated dose control
USD887632S1 (en) 2017-09-14 2020-06-16 Pax Labs, Inc. Vaporizer cartridge
WO2020141178A1 (fr) * 2018-12-31 2020-07-09 Philip Morris Products S.A. Préparation de nicotine liquide comprenant un solvant partiellement hydrosoluble
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WO2023135408A1 (fr) * 2022-01-14 2023-07-20 Nicoventures Trading Limited Matériau aérosolisable
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US20180325164A1 (en) 2018-11-15

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