WO2014150881A1 - Produits contenant de la nicotine et de l'anatabine et leurs procédés de fabrication - Google Patents

Produits contenant de la nicotine et de l'anatabine et leurs procédés de fabrication Download PDF

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Publication number
WO2014150881A1
WO2014150881A1 PCT/US2014/024451 US2014024451W WO2014150881A1 WO 2014150881 A1 WO2014150881 A1 WO 2014150881A1 US 2014024451 W US2014024451 W US 2014024451W WO 2014150881 A1 WO2014150881 A1 WO 2014150881A1
Authority
WO
WIPO (PCT)
Prior art keywords
nicotine
anatabine
product
tobacco
containing product
Prior art date
Application number
PCT/US2014/024451
Other languages
English (en)
Inventor
Dongmei Xu
James Arthur Strickland
Jeffery EDMISTON
Original Assignee
Dongmei Xu
James Arthur Strickland
Edmiston Jeffery
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 Dongmei Xu, James Arthur Strickland, Edmiston Jeffery filed Critical Dongmei Xu
Priority to EP14715188.0A priority Critical patent/EP2967121A1/fr
Priority to CA2905942A priority patent/CA2905942A1/fr
Publication of WO2014150881A1 publication Critical patent/WO2014150881A1/fr

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
    • A24B15/18—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
    • 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
    • A24B15/36—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

Definitions

  • This disclosure generally relates to nicotine-containing products.
  • Tobacco is a complex mixture of compounds with many different sensorial attributes. Many compounds in tobacco and tobacco smoke play a role in the sensorial aspects of tobacco products.
  • the present disclosure describes nicotine-containing products that also contain anatabine and methods of making such products.
  • a nicotine-containing product comprising anatabine.
  • the ratio of anatabine to nicotine is greater than 5:95. In some embodiments, the ratio of anatabine to nicotine is greater than 10:90. In some embodiments, the ratio of anatabine to nicotine is greater than 15:85.
  • the nicotine is synthetic nicotine. In some embodiments, the nicotine is tobacco-derived nicotine. In some embodiments, the anatabine is synthetic anatabine. In some embodiments, the anatabine is tobacco-derived anatabine.
  • Representative nicotine-containing products include, without limitation, a smokeable product and a smokeless product.
  • Representative smokeable products include, without limitation, a combustible product and a non-combustible product.
  • combustible products include a cigarette and a cigar.
  • Representative non-combustible products include, without limitation, an e-cigarette, an electronic smoking article, an aerosolized vapor products, and a heated tobacco product.
  • Representative smokeless products include snus, a pouch, a tab, a film, a stick, a woven product, a meltblown product, or a sintered piece.
  • such a product further includes an additive, a sweetener, a flavorant, a polymer, a fiber, filler, a plasticizer, or combinations thereof.
  • a method of making a nicotine-containing product typically includes providing a nicotine-containing product and introducing anatabine into a nicotine-containing product in an amount such that the anatabine to nicotine ratio is greater than 5:95. In some embodiments, the ratio of anatabine to nicotine is greater than 10:90. In some embodiments, the ratio of anatabine to nicotine is greater than 15:85.
  • the nicotine is synthetic nicotine. In some embodiments, the nicotine is tobacco-derived nicotine. In some embodiments, the anatabine is synthetic anatabine. In some embodiments, the anatabine is tobacco-derived anatabine.
  • Figure 1 shows the pathway by which nicotine and anatabine are produced.
  • Anatabine [2R,(+)]-l,2,3,6-Tetrahydro-2,3'-bipyridine
  • Anatabine has been shown to have affinity for nicotine acetylcholine receptors (Maciuk et al., 2008, J. Pharm. Biomed. Anal., 48:238-46) and has been shown to inhibit monoamine oxidase (US Patent No. 6,569,470) and the enzyme responsible for nicotine metabolism (Denton et al., 2004, Biochem. Pharmacol., 67:751-6).
  • anatabine may accentuate the nicotine response by binding to the nicotine receptor; anatabine may prolong the increased levels of neurotransmitters in the brain by inhibiting monoamine oxidase; and/or anatabine may extend the time between product use by inhibiting the enzyme responsible for nicotine metabolism.
  • the level of anatabine in dark tobacco is typically less than about 5% of the level of nicotine, but can be as high as 7% in burley tobacco.
  • Ratios of anatabine to nicotine can be greater than that found in cured tobacco leaf; for example, the ratio of anatabine to nicotine can be greater than about 5:95 (e.g., greater than about 6:94, 7:93, 8:92, 9:91, 10:90, 15:85, 20:80, 25:75, 30:70, 35:65, 40:60, 45:55, or 50:50 anatabine-to-nicotine).
  • Nicotine-containing products that include anatabine can take any number of forms, and can include, for example, smokeable products (e.g., combustible smokeable products, non-combustible vapor-generating products (e.g., electronic e-cigarettes), smokeless products, and liquid aerosol formulations for use in, e.g., an electronic smoking article.
  • Smokeless products also can take many forms including, without limitation, dissolvable or disintegratable products (e.g., tabs, films, sticks), loose and pre-formed moist snuff (e.g., woven products, pouches, snus), and mouth-stable polymer products (e.g., meltblown products and sintered pieces).
  • the nicotine in a nicotine-containing product that also includes anatabine can be tobacco-derived nicotine, synthetic nicotine, or a combination thereof.
  • the anatabine in such a product can be tobacco-derived anatabine, synthetic anatabine, or a combination thereof.
  • Tobacco-derived nicotine and/or tobacco-derived anatabine generally include one or more tobacco organoleptic components in addition to the nicotine and/or anatabine.
  • Tobacco-derived nicotine and/or tobacco-derived anatabine can be extracted from raw tobacco (e.g., green leaf) or processed tobacco.
  • Processed tobacco can include cured tobacco (e.g., dark air-cured, dark fire-cured, flue cured), fermented tobacco, conditioned tobacco and/or pasteurized tobacco (see, for example, U.S. Patent Nos. 4,528,993; 4,660,577; 4,848,373; and 5,372,149, and U.S. Publication Nos. 2004/0118422 and 2005/0178398).
  • cured tobacco e.g., dark air-cured, dark fire-cured, flue cured
  • fermented tobacco conditioned tobacco and/or pasteurized tobacco
  • conditioned tobacco and/or pasteurized tobacco see, for example, U.S. Patent Nos. 4,528,993; 4,660,577; 4,848,373; and 5,372,149, and U.S. Publication Nos. 2004/0118422 and 2005/0178398).
  • Tobacco-derived nicotine and/or tobacco-derived anatabine can be obtained by mixing tobacco (i.e., raw or processed) with water or another solvent (e.g., ethanol) and removing the insoluble tobacco material. Nicotine and/or anatabine can be concentrated or purified from a tobacco extract using routine methods. Representative methods of obtaining nicotine and other alkaloids from tobacco are described, for example, in U.S. Patent Nos. 2,162,738; 3,139,436; 3,396,735; 4,153,063; 4,448,208; 5,487,792; and 5,684,155. In addition, nicotine, anatabine, or a salt thereof, can be produced synthetically. See, for example, U.S. Patent Nos. 4,442,292; 4,452,984; 6,995,265; 7,112,678; and 8,207,346.
  • a nicotine-containing product that includes anatabine can be substantially free of tobacco plant tissue.
  • tobacco plant tissue refers to processed or non-processed cellulosic parts (e.g., leaves, stems) of a member of the genus Nicotiana, but does not include extracts of tobacco (e.g., tobacco-derived nicotine or tobacco-derived anatabine).
  • a nicotine-containing product that includes anatabine also can include one or more organoleptic components extracted from raw or processed tobacco, yet be substantially free of tobacco plant tissue.
  • a nicotine-containing product that includes anatabeine as described herein also can include one or more additives, sweeteners, and/or flavorants, as well as one or more polymers, fibers, fillers, plasticizers, and/or other processing aids to provide a favorable flavor profile and tactile experience.
  • additives sweeteners, and/or flavorants
  • polymers such as polyethylene glycol dimethacrylate, polypropylene glycol dimethacrylate, polysulfate, polysulfate, polysulfate, polyethylene glycol dime, polyethylene glycol dimethoxysulfate, terethoxys, terpolymer, polymers, fibers, fillers, plasticizers, and/or other processing aids to provide a favorable flavor profile and tactile experience.
  • polymers fibers, fillers, plasticizers, and/or other processing aids
  • flavorants can be used in a nicotine-containing product that contains anatabine.
  • the flavorants can be natural or artificial.
  • suitable flavorants include wintergreen, cherry and berry type flavorants, various liqueurs and liquors (such as Dramboui, bourbon, scotch, and whiskey) spearmint, peppermint, lavender, cinnamon, cardamon, apium graveolents, clove, cascarilla, nutmeg, sandalwood, bergamot, geranium, honey essence, rose oil, vanilla, lemon oil, orange oil, Japanese mint, cassia, caraway, cognac, jasmin, chamomile, menthol, ylangylang, sage, fennel, ginger, anise, coriander, coffee, and liquorish.
  • flavorants can be encapsulated.
  • a nicotine-containing product that includes anatabine as described herein can include a polymer.
  • a polymer can be any of a number of different biocompatible and biostable polymers.
  • the polymer is a thermoplastic polymer or a thermoplastic elastomer.
  • Representative polymers include, without limitation, polyurethanes, silicon polymers, polyesters, polyacrylates, polyethylenes, polypropylenes, polyetheramides, polystyrenes (e.g., acrylonitrile butadiene styrene, high impact polystyrenes (HIPS)) polyvinyl alcohols, polyvinyl acetates, polyvinyl chlorides, polybutyl acetates, butyl rubbers (e.g., polyisobutylenes), SEBS, SBS, and mixtures and copolymers thereof.
  • the polymer is a food-grade or medical-grade polymer (e.g., medical-grade polyurethane).
  • a nicotine-containing product containing anatabine also can include fillers such as starch, dicalcium phosphate, lactose, sorbitol, mannitol, and microcrystalline cellulose, calcium carbonate, dicalcium phosphate, calcium sulfate, clays, silica, glass particles, sodium lauryl sulfate (SLS), glyceryl palmitostearate, sodium benzoate, sodium stearyl fumarate, talc, and stearates (e.g., Mg or K), and waxes (e.g., glycerol monostearate, propylene glycol monostearate, and acetylated monoglycerides), stabilizers (e.g., ascorbic acid and monosterol citrate, BHT, or BHA), disintegrating agents (e.g., starch, sodium starch glycolate, cross caramellose, cross linked PVP), pH stabilizers, or preservatives.
  • fillers such as starch
  • a nicotine-containing product that includes anatabine also can include one or more plasticizers.
  • Plasticizers can soften the product and thus increase its flexibility. Suitable plasticizers include propylene glycol, glycerin, vegetable oil, and medium chain triglycerides. In some embodiments, the plasticizer can include phthalates. Esters of polycarboxylic acids with linear or branched aliphatic alcohols of moderate chain length can also be used as plasticizers.
  • Methods of making the nicotine-containing products described herein are known in the art. Methods of making such products often utilize automated or semi-automated processes, which can include cutting, pressing, shaping, tableting, rolling, dipping, coating, heating, melting, drying, sintering, melt blowing, needling, pouching, and combinations thereof.
  • automated or semi-automated processes can include cutting, pressing, shaping, tableting, rolling, dipping, coating, heating, melting, drying, sintering, melt blowing, needling, pouching, and combinations thereof.
  • the particular product and the method by which it is made will determine when and in what form (e.g., tobacco-derived or synthetic) the anatabine is introduced.
  • the anatabine can be introduced prior to any processing; in other products and/or processes, the anatabine can be introduced during processing; while yet in other products and/or processes, the anatabine can be introduced after processing is complete but prior to packaging. Depending upon the source of the nicotine and at what point the nicotine is introduced, the anatabine can be introduced together with the nicotine or separately.
  • the nicotine-containing products described herein that include anatabine can be packaged in any type of conventional or non-conventional manner.
  • a plurality of nicotine-containing products that include anatabine can be packaged in a container having a lid.
  • a plurality of nicotine-containing products that include anatabine can be stacked and packaged in a paper, plastic, and/or aluminum foil tube.
  • the packaging can have a child-resistant lid.

Abstract

La présente invention concerne des produits contenant de la nicotine qui contiennent également de l'anatabine. L'invention concerne également des procédés de fabrication de tels produits.
PCT/US2014/024451 2013-03-15 2014-03-12 Produits contenant de la nicotine et de l'anatabine et leurs procédés de fabrication WO2014150881A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP14715188.0A EP2967121A1 (fr) 2013-03-15 2014-03-12 Produits contenant de la nicotine et de l'anatabine et leurs procédés de fabrication
CA2905942A CA2905942A1 (fr) 2013-03-15 2014-03-12 Produits contenant de la nicotine et de l'anatabine et leurs procedes de fabrication

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201361786344P 2013-03-15 2013-03-15
US61/786,344 2013-03-15

Publications (1)

Publication Number Publication Date
WO2014150881A1 true WO2014150881A1 (fr) 2014-09-25

Family

ID=50434301

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2014/024451 WO2014150881A1 (fr) 2013-03-15 2014-03-12 Produits contenant de la nicotine et de l'anatabine et leurs procédés de fabrication

Country Status (4)

Country Link
US (1) US20140261479A1 (fr)
EP (1) EP2967121A1 (fr)
CA (1) CA2905942A1 (fr)
WO (1) WO2014150881A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NO20170683A1 (en) * 2017-04-24 2018-10-25 Swedish Match North Europe Ab A flavoured moist oral pouched nicotine product comprising triglyceride
WO2018197454A1 (fr) 2017-04-24 2018-11-01 Swedish Match North Europe Ab Produit humide et aromatisé à base de nicotine sous forme de sachet pour administration orale comprenant un triglycéride
WO2019115778A1 (fr) 2017-12-15 2019-06-20 Swedish Match North Europe Ab Produit humide et aromatisé à base de nicotine sous forme de sachet pour administration orale comprenant un triglycéride

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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
US10980273B2 (en) 2013-11-12 2021-04-20 VMR Products, LLC Vaporizer, charger and methods of use
US10159282B2 (en) 2013-12-23 2018-12-25 Juul Labs, Inc. Cartridge for use with a vaporizer device
USD842536S1 (en) 2016-07-28 2019-03-05 Juul Labs, Inc. Vaporizer cartridge
US20160366947A1 (en) 2013-12-23 2016-12-22 James Monsees Vaporizer apparatus
US10076139B2 (en) 2013-12-23 2018-09-18 Juul Labs, Inc. Vaporizer apparatus
KR102256889B1 (ko) 2013-12-23 2021-05-31 쥴 랩스, 인크. 기화 디바이스 시스템 및 방법
US10058129B2 (en) 2013-12-23 2018-08-28 Juul Labs, Inc. Vaporization device systems and methods
USD825102S1 (en) 2016-07-28 2018-08-07 Juul Labs, Inc. Vaporizer device with cartridge
KR102627987B1 (ko) 2014-12-05 2024-01-22 쥴 랩스, 인크. 교정된 투여량 제어
DE202017007467U1 (de) 2016-02-11 2021-12-08 Juul Labs, Inc. Befüllbare Verdampferkartusche
EP3419443A4 (fr) 2016-02-11 2019-11-20 Juul Labs, Inc. Cartouches fixées de manière sure pour des dispositifs de vaporisation
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USD849996S1 (en) 2016-06-16 2019-05-28 Pax Labs, Inc. Vaporizer cartridge
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USD836541S1 (en) 2016-06-23 2018-12-25 Pax Labs, Inc. Charging device
USD848057S1 (en) 2016-06-23 2019-05-07 Pax Labs, Inc. Lid for a vaporizer
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Cited By (6)

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Publication number Priority date Publication date Assignee Title
NO20170683A1 (en) * 2017-04-24 2018-10-25 Swedish Match North Europe Ab A flavoured moist oral pouched nicotine product comprising triglyceride
WO2018197454A1 (fr) 2017-04-24 2018-11-01 Swedish Match North Europe Ab Produit humide et aromatisé à base de nicotine sous forme de sachet pour administration orale comprenant un triglycéride
NO343402B1 (en) * 2017-04-24 2019-02-25 Swedish Match North Europe Ab A flavoured moist oral pouched nicotine product comprising triglyceride and a method for manufacturing thereof.
US11717017B2 (en) 2017-04-24 2023-08-08 Swedish Match North Europe Ab Flavoured moist oral pouched nicotine product comprising triglyceride
WO2019115778A1 (fr) 2017-12-15 2019-06-20 Swedish Match North Europe Ab Produit humide et aromatisé à base de nicotine sous forme de sachet pour administration orale comprenant un triglycéride
US11844368B2 (en) 2017-12-15 2023-12-19 Swedish Match North Europe Ab Flavoured moist oral pouched nicotine product comprising monoglyceride

Also Published As

Publication number Publication date
CA2905942A1 (fr) 2014-09-25
US20140261479A1 (en) 2014-09-18
EP2967121A1 (fr) 2016-01-20

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