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WO2005048980A1 - Composition de film pouvant etre consomme oralement - Google Patents

Composition de film pouvant etre consomme oralement Download PDF

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Publication number
WO2005048980A1
WO2005048980A1 PCT/KR2004/000218 KR2004000218W WO2005048980A1 WO 2005048980 A1 WO2005048980 A1 WO 2005048980A1 KR 2004000218 W KR2004000218 W KR 2004000218W WO 2005048980 A1 WO2005048980 A1 WO 2005048980A1
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WO
WIPO (PCT)
Prior art keywords
film composition
composition according
orally consumable
consumable film
agent
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/KR2004/000218
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English (en)
Inventor
Myung-Kyo Shin
Kil-Jin Ahn
Kang-Mo Sung
Yong-Hyun Jung
Young-Sook Kwon
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.)
KBP Co Ltd
Original Assignee
KBP Co 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 KBP Co Ltd filed Critical KBP Co Ltd
Publication of WO2005048980A1 publication Critical patent/WO2005048980A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
    • A61K9/006—Oral mucosa, e.g. mucoadhesive forms, sublingual droplets; Buccal patches or films; Buccal sprays
    • 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
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin

Definitions

  • the present invention reLLates to an orally consumable film composition containing starch and alginate at a ratio of 1:2.5 to 1:4.
  • a film prepared using such a composition has excellent tensile strength and elongation and is useful in the delivery of various pharmaceutically active agents .
  • a mouthspray that is a portable oral cleansing product typically generates a noise, and attracts public attention when used in public places .
  • edible films were developed using various biopolymers.
  • a representative example of the biopolymers used in preparation of the edible films is pullulan, and use of the pullulan is described in a plurality of literatures.
  • U.S. Pat. No. 6,596,298 discloses a film including pullulan and antimicrobially effective amounts of thymol, methylsalicylate, eucalyptol and menthol.
  • the present inventors found that a mixture of starch and alginate in a predetermined ratio has physical properties, in particular, tensile strength and elongation, suitable as a film-forming agent to produce orally consumable film, is not self-adhering, dissolves rapidly upon oral application and can contain relatively higher amounts of oral care agents such as antimicrobial/flavoring agents, resulting in an excellent oral cleaning effect. Based on this finding, the present inventors completed this invention .
  • the present invention relates to an orally consumable film composition, which is characterized by comprising a mixture of starch and alginate at a ratio of 1:2.5 to 1:4.0.
  • the conventional film-forming agents include pullulan, alginate, starch, gelatin, and diverse gums, for example, carageenan, xanthan gum, locust bean gum (LBG) and gellan gum. These biopolymers are dissolved in water in predetermined amounts, casted and then dried to form films.
  • the above film-forming agents have superior physical properties when used in combination compared to being used individually.
  • the present inventors found that, when used as a film-forming agent, a mixture of starch and alginate at a ratio of 1:2.5 to 1:4.0 has excellent physical properties, in particular, tensile strength and elongation, and is capable of containing high amounts of various oral care agents, such as antimicrobial agents, flavoring agents and oral malodor-removing agents.
  • the mixture of starch and alginate is suitable for preparation of orally consumable films for oral cleaning.
  • the starch used to produce the film composition of the present invention includes all starch derived from naturally occurring sources. Also suitable are starches derived from a plant obtained by various breeding techniques including cross-breeding, translocation, inversion and transformation.
  • Typical sources for the starches are cereals, tubers, roots, legumes and fruits, which comprise corn, potato, sweet potato, banana, barley, wheat, rice, sago, amaranth, tapioca, arrowroot, canna and sorghum.
  • the starch used in the film composition may be modified to meet desired film properties, as follows: the film should have sufficient tensile strength and elongation and be not deformed upon film formation, should be moisture-resistant to prevent self-adhering, and should be rapidly dissolved in an aqueous solution. To achieve these film properties, the starch may be modified by methods known in the art, such as physical, chemical and enzymatic modifications. Examples of physically modified starches include sheared starches or thermally inhibited starches .
  • Examples of chemically modified starches include cross-linked derivatives, acetylated derivatives, organically esterified derivatives, hydroxyethylated derivatives, hydroxypropylated derivatives, phosphorylated derivatives, inorganically esterified derivatives, cationic derivatives, anionic derivatives, zwitterionic derivatives, succinate derivatives and substituted succinate derivatives.
  • Such modifications are well known in the art.
  • Perfectamyl AC esterified potato starch, Kreation MB modified tapioca starch and Perfectamyl HT2X modified tapioca starch are known.
  • hydroxyalkylated starches such as hydroxypropylated starches or hydroxyethylated starches
  • succinated starches such as octenylsuccinated starches or dodecylsuccinated starches.
  • the hydroxyalkylated starches are more beneficial in order to offer better elongation to films prepared by using the same.
  • the starches having properties suitable in the practice of the present invention may be purified during the processing by a method known in the art .
  • the alginate used at a mixed state with the starch may be derived from diverse sources, for example, brown algae or microorganisms, and used as a gel-forming agent, a coagulating agent and a dietary fiber due to its very strong affinity to divalent metals.
  • the alginate is used as a stabilizing agent of highly viscous foods, such as ice creams, sorbets, syrups and sweet red-bean soup, as well as in the preparation of adhesives, lubricants, films, fibers, and the like.
  • the alginate is used in the form of sodium alginate, for example, Manucol LB.
  • the ratio of the starch to the alginate ranged from 1:2.5 to 1:4, the resulting film was excellent in both tensile strength and elongation, and had increased contents of pharmaceutically active agents such as flavoring agents and antimicrobial agents .
  • the ratio of the starch to the alginate, used as a film-forming agent contained in the orally consumable film composition of the present invention ranges from 1:3.0 to 1:3.5.
  • a film prepared using such a composition of the present invention has physical properties suitable for use as an orally consumable film, in particular, a good tensile strength (higher than 20 Mpa, preferably, higher than 25 Mpa) , a good elongation (higher than 3%, preferably, higher than 5%) and a high solubility (dissolved within several seconds) .
  • a good tensile strength higher than 20 Mpa, preferably, higher than 25 Mpa
  • a good elongation higher than 3%, preferably, higher than 5%
  • a high solubility dissolved within several seconds
  • plasticizing agents examples include polyols, which are exemplified by ethylene glycol, propylene glycol, sugar alcohols (e.g., sorbitol, mannitol, maltitol, lacticol, xylitol, etc.) and mono-, di- and oligo-saccharides (e.g., fructose, glucose, sucrose, maltose, lactose and high fructose corn syrup and ascorbic acid) , polycarboxylic acids, which are exemplified by citric acid, maleic acid, succinic acid, polyacrylic acid and polymaleic acid) , and polesters, which are exemplified by glycerin, triacetate, acetylated monoglyceride, diethyl phthalate, triethyl citrate, tributyl citrate, acetyl triethyl citrate and acetyl tributyl citrate)
  • plasticizing agents increase elongation and solubility but reduce tensile strength. It is more preferable that such softners are used in combination than individually.
  • sorbitol, glycerine, propylene glycol, etc. are used together.
  • the content of the plasticizing agents is about 0 to 20% by weight and preferably, about 1 to 5% by weight, based on the total weight of the film composition.
  • the sorbitol contained in the film composition may increase the moisture content in films .
  • the term "the total weight of the film composition" is intended to indicate the total weight of substances used in the orally consumable film of the present invention.
  • biopolymers as stabilizing agents may be added to the film composition.
  • the biopolymers include carageenan, LBG (locust bean gum) , xanthan gum and gellan. These biopolymers increase viscosity of the film composition and tensile strength. Due to such properties, when a film containing high-content flavors and oils is intended to be prepared, the biopolymers are capable of preventing the film from being easily deformed.
  • the content of the biopolymers is about 0 to 5% by weight, and preferably, about 0.5 to 2% by weight, based on the total weight of the film composition.
  • Molecular weights of the high molecular weight film- forming agents are important in the film formation.
  • film-forming agents having a molecular weight ranging from 150 kDa (kilodaltons) to 300 kDa.
  • the film-forming agents When having a molecular weight exceeding the range, the film-forming agents have remarkably deteriorated physical properties.
  • the film-forming agents when the film-forming agents have a molecular weight less than the range, the resulting film is easily deformed and more difficult to handle upon maturation, slitting and cutting during its processing.
  • Any suitable food-grade bulk filler may be added to the present composition. This can reduce any slimy texture as well as provide structure to the film.
  • the filler examples include microcrystalline cellulose, cellulose polymers, magnesium carbonate, calcium carbonate, ground limestone, silicates, clay, talc, titanium dioxide, mono- calcium phosphate, di-calcium phosphate and tri-calcium phosphate.
  • the microcrystalline cellulose is preferable, which is exemplified by Avicel.
  • the content of the filler is about 0 to 5% by weight, and preferably, about 0.1 to 1% by weight, based on the total weight of the film composition.
  • the present composition may further include antimicrobial/flavoring agents .
  • flavoring agents that can be used include those known to the skilled artisan, such as natural and -artificial flavors . These flavoring agents may be chosen from synthetic flavor oils and flavoring aromatics, and/or oils, oleo resins and extracts derived from plants, leaves, flowers, fruits and the like, and combinations thereof. Representative flavor oils include spearmint oil, cinnamon oil, peppermint oil, clove oil, bay oil, thyme oil, cedar leaf oil, oil of nutmeg, oil of sage, and oil of bitter almonds.
  • sweetening agents such as vanilla, chocolate, coffee, cocoa and citrus oil, including lemon, orange, grape, lime and grapefruit; and fruit essences including apple, pear, peach, strawberry, raspberry, cherry, plum, pineapple, apricot and the like.
  • sweetening agents may be used individually or in admixture.
  • Commonly used flavoring agents include mints such as peppermint, artificial vanilla, cinnamon derivatives, and various fruit flavors, whether employed individually or in admixture.
  • Flavoring agents such as aldehydes and esters including cinnamyl acetate, cinnamaldehyde, citral, diethylacetal, dihydrocarvyl acetate, eugenyl formate, p-methylanisole, and the like may also be used.
  • any flavoring agent or food additive such as those described in Chemicals Used in Food Processing, publication 1274 by the National Academy of Sciences, pages 63-258, may be used.
  • aldehyde flavoring agents include, but are not limited to acetaldehyde (apple) ; benzaldehyde (cherry, almond) ; cinnamic aldehyde (cinnamon); citral, i.e., alpha citral (lemon, lime); neral, i.e.
  • the flavoring agent is an oil type including a water- soluble powder type.
  • oil-type flavoring agents menthol, peppermint and methylsalicylate have antimicrobial efficacy.
  • an emulsifying agent may be added to the film composition to allow for the blending of the flavoring agent with water.
  • the amount of flavoring agent employed may vary depending on a plurality of factors such as flavor type, individual flavor and strength desired. Such variations are within the capabilities of those skilled in the art without the need for undue experimentation.
  • the content of the flavoring agent is about 0.1 to 20% by weight, and preferably, about 1 to 5% by weight, based on the total weight of the film composition.
  • the flavoring agent having antimicrobial efficacy such as menthol, peppermint or methylsalicylate
  • an emulsifying agent to allow for the blending with water- soluble substances .
  • the emulsifying agent include glycerin fatty acid esters, sucrose fatty acid esters and lecithin.
  • the highly hydrophilic sucrose fatty acid ester, sucrose fatty acid ester S-1670 may be used in an amount of about 0 to 5% by weight, and preferably, about 0.1 to 2.0% by weight, based on the total weight of the film composition.
  • the present composition may include sulfur-precipitating agents to reduce oral malodor. These agents bind with, and inactivate, the volatile sulfur compounds causing oral malodor.
  • Sulfur precipitating agents useful in the present invention include metal salts such as copper salts and zinc salts. Preferred salts include copper gluconate, zinc citrate and zinc gluconate.
  • the present composition may further include sweeteners .
  • suitable sweeteners include water-soluble sweetening agents such as monosaccharides, disaccharides and polysaccharides such as xylose, ribose, glucose, mannose, galactose, fructose, sucrose, maltose, invert sugar, partially hydrolyzed starch, corn syrup solids, dihydrochalcones, monellin and steviosides; water-soluble artificial sweeteners such as the soluble saccharin salts, i.e., sodium or calcium saccharin salts, cyclamate salts, the sodium, ammonium or ' calcium salt of 3,4-dihydro- ⁇ -methyl- 1,2, 3-oxathiazine-4-one-2,2-dioxide, the potassium salt of 3, 4-dihydro- ⁇ -methyl-l, 2, 3-oxathiazine-4-one-2, 2-dioxide (acesulfame-K) , the free acid form of saccharin, and the like; dipeptide-
  • sucralose, acesulfame-K, aspartame and steviosides are frequently used.
  • sucralose, acesulfame-K and aspartame are used in an admixture.
  • the content of the sweetening agents is about 0.01% to 2.0% by weight, and preferably, about 0.2% to 1.0% by weight, based on the total weight of the film composition.
  • the present composition may further include acidifiers . The acidifiers stimulate saliva secretion, affect taste of films prepared using the present composition, and attribute to improvement of gel strength.
  • the acidifiers include various acids, such as citric acid, lactic acid, malic acid, succinic acid, ascorbic acid, adipic acid, fumaric acid and tartaric acid. Preferable are citric acid and malic acid.
  • the content of the acidifiers is about 0 to 2.0% by weight, and preferably, about 0.1 to 1.0% by weight, based on the total weight of the film composition.
  • the present composition may further include coloring agents.
  • the coloring agents are used in amounts effective to produce a desired color. Examples of the coloring agents include colors of natural foods and edible dyes. Such coloring agents are typically known as FD&D dyes.
  • the present composition may include stabilizing agents, emulsifying agents, cooling agents and various therapeutic agents for medical use including vitamins.
  • the therapeutic agents can achieve multiple effects when used in combination with the above antimicrobial agents for oral cleaning.
  • the present composition may further include pharmaceutical active agents.
  • pharmaceutical active agents as used herein, is intended to indicate agents other than foods, which promote a structural and/or functional change in and/or on bodies to which they have been administered. These agents should be physiologically acceptable and compatible with the film.
  • Suitable pharmaceutically active agents include, but are not limited to antimicrobial agents, such as triclosan, cetyl pyridium chloride, domiphen bromide, quaternary ammonium salts, zinc compounds, sanguinarine, fluorides, alexidine, octonidine, EDTA, and the like; non-steroidal anti-inflammatory drugs, such as aspirin, acetaminophen, ibuprofen, ketoprofen, diflunisal, fenoprofen calcium, naproxen, tolmetin sodium, indomethacin, and the like; anti-tussives, such as benzonatate, caramiphen edisylate, menthol, dextromethorphan hydrobromide, chlophedianol hydrochloride, and the like; decongestants, such as pseudoephedrine hydrochloride, phenylepherine, phenylpropanolamine, pseudoephedrine
  • Preferred pharmaceutically active agents includes chlorpheniramine maleate, brompheniramine maleate, dexchlorpheniramine, triprolidine hydrochloride, acrivastine, azatadine maleate, loratidine, phenylephrine hydrochloride, dextromethorphan hydrochloride, ketoprofen, sumatriptan succinate, zolmitriptan, loperamide, famotidine, nicotine, caffeine, diphenhydramine hydrochloride, and pseudoephedrine hydrochloride, and their amounts per strip are well known in the art .
  • the film composition containing pharmaceutically active agents may also include a triglyceride .
  • the triglyceride examples include vegetable oils such as corn oil, sunflower oil, peanut oil, olive oil, canola oil, soybean oil and mixtures thereof.
  • the film composition containing pharmaceutically active agents may also include a preservative, such as sodium benzoate and potassium sorbate; a polyethylene oxide compound; and propylene glycol.
  • the pharmaceutically active agent used in the film may be coated to mask the taste of the active ingredient and to gain other additional effects.
  • a film prepared using the present composition having the above composition has a tensile strength of 20 Mpa or more, and preferably 25 Mpa or more, and an elongation of 3% or more, and preferably 5% or more.
  • the film is easy to handle during and after processing, and can contain antimicrobial/flavoring agents in higher contents.
  • the film is effective in oral cleaning and delivery of additional medicinals.
  • 0.144 g of Avicel was added to 71.891 g of water in a container at room temperature, and homogeneously mixed for 20 min.
  • 0.479 g of sucrose fatty acid ester S-1670 was added to the above solution and mixed for 20 min.
  • 1.198 g of sorbitol, 1.198 g of glycerin and 0.240 g of propylene glycol were added to the solution, and heated to 80°C. When the temperature reached 80°C, the heating was stopped, and 14.378 g of alginate (manucol LB), 0.288 g of carageenan, 0.192 g of LBG and 0.144 g of xanthan gum were added to the resulting solution, followed by mixing for one hour.
  • TS Tensile strength
  • E elongation
  • the films were equilibrated in water contents by being incubated in an incubator at 25°C under a relative humidity of 50% for 48 hrs.
  • the films were cut with a size of 2.54cm(W)x 10cm(L), and the test was carried out with a crosshead speed of 500 mm/min and a grip separation of 50 mm. The test was repeated nine times, and mean and SD values were calculated. Ine measured tensile strength values were expressed as Mpa, while the measured elongation values were expressed as %. As a result, the films were found to have a tensile strength of 28.230 Mpa and an elongation of 7.767%.
  • 0.221 g of Avicel was added to 73.765 g of water in a container at room temperature, and homogeneously mixed for 20 min.
  • 0.738 g of sucrose fatty acid ester S-1670 was added to the above solution and mixed for 20 min.
  • 1.844 g of sorbitol, 1.844 g of glycerin and 0.369 g of propylene glycol were added to the solution, and heated to 80°C. When the temperature reached 80°C, the heating was stopped, 0.443 g of carageenan, 0.295 g of LBG and 0.221 g of xanthan gum were added to the resulting solution, followed by mixing for one hour.
  • 0.160 g of Avicel was added to 69.309 g of water in a container at room temperature, and homogeneously mixed for 20 min.
  • 0.533 g of sucrose fatty acid ester S-1670 was added to the above solution and mixed for 20 min.
  • 1.333 g of sorbitol, 1.333 g of glycerin and 0.267 g of propylene glycol were added to the solution, and heated to 80°C. When the temperature reached 80°C, the heating was stopped, 21.326 g of alginate (manucol LB) and 0.320 g of carageenan, 0.213 g of LBG and 0.160 g of xanthan gum were added to the resulting solution, followed by mixing for one hour.
  • COMPARATIVE EXAMPLE 3 1.054 g of Avicel was added to 71.487 g of water in a container at room temperature, and homogeneously mixed for 20 min. 0.248 g of sucrose fatty acid ester S-1670 was added to the above solution and mixed for 20 min. Subsequently, 1.162 g of sorbitol, 1.162 g of glycerin and 0.858 g of propylene glycol were added to the solution, and heated to 80°C.
  • the obtained admixture was coated using a coating device, air-dried, and slitted with a desired size.
  • the slitted samples were maturated for three to seven days. After the maturation was completed, the samples were cut with a desired size, thus yielding films.
  • Tensile strength (TS) and elongation (E) of the films were measured according to the same method as in Example 1. As a result, the films were found to have a tensile strength of 15.890 Mpa and an elongation of 4.941%.
  • the obtained admixture was coated using a coating device, air-dried, and slitted with a desired size.
  • the slitted samples were maturated for three to seven days. After the maturation was completed, the samples were cut with a desired size, thus yielding films.
  • Tensile strength (TS) and elongation (E) of the films were measured according to the same method as in Example 1. As a result, the films were found to have a tensile strength of 12.020 Mpa and an elongation of 3.218%.
  • compositions of the films prepared in Example 1 and Comparative Examples 1 to 4 and the measured tensile strength (TS) and elongation (E) values were summarized in Table 1, below.
  • Example 1 As shown in Table 1, the case of using starch and alginate as film-forming substances at a ratio of 1:3 to 1:3.5 (Example 1) displayed excellent tensile strength and elongation, compared to the cases of using starch alone (Comparative Example 1), alginate alone (Comparative Example 2) and both starch and alginate at a different ratio from that in Example 1 (Comparative Examples 3 and 4).
  • Example 2 As shown in Table 1, the case of using starch and alginate as film-forming substances at a ratio of 1:3 to 1:3.5 (Example 1) displayed excellent tensile strength and elongation, compared to the cases of using starch alone (Comparative Example 1), alginate alone (Comparative Example 2) and both starch and alginate at a different ratio from that in Example 1 (Comparative Examples 3 and 4).
  • Films were manufactured with the compositions listed in Table 2, below, according to the same method as in Example 1. The measured physical properties of the films are given in Table 2.
  • EXAMPLE 9 Films were successfully manufactured with the compositions containing a particular therapeutically active agent, listed in Table 3, below, according to the same method as in Example 1.
  • EXAMPLE 10 Films were successfully manufactured with the compositions containing 2.60 g of acrivastine as a therapeutically active agent, listed in Table 3, below, according to the same method as in Example 1.
  • EXAMPLE 11 Films were successfully manufactured with the compositions containing 3.25 g of loratadine as a therapeutically active agent, listed in Table 3, below, according to the same method as in Example 1.
  • EXAMPLE 12 Films were successfully manufactured with the compositions containing 2.60 g of anhydrous caffeine as a particular therapeutically active agent, listed in Table 3, below, according to the same method as in Example 1.
  • EXAMPLE 13 Films were successfully manufactured with the compositions containing 0.65 g of nicotine as a particular therapeutically active agent, listed in Table 3, below, according to the same method as in Example 1.
  • the present composition that is characterized by containing starch and alginate at a ratio of 1:2.5 to 1:4 offers excellent tensile strength and elongation to films prepared using the same, and allows the films to contain a large amount of antimicrobial/flavoring agents. Therefore, the present composition makes it possible to manufacture films effective in oral cleaning and delivery of additional medicinal agents .

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
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Abstract

L'invention concerne une composition de film pouvant être consommé oralement, comprenant de l'amidon et de l'alginate selon un rapport compris entre 1 : 2,5 et 1 : 4. La composition comprend également des agents antimicrobiens, des agents aromatisants, des agents de remplissage, des agents plastifiants, des agents stabilisants, des agents stimulant la sécrétion salivaire, des agents édulcorants, des agents pharmaceutiquement actifs et analogues.
PCT/KR2004/000218 2003-11-18 2004-02-05 Composition de film pouvant etre consomme oralement Ceased WO2005048980A1 (fr)

Applications Claiming Priority (2)

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KR10-2003-0081876 2003-11-18
KR1020030081876A KR20050048056A (ko) 2003-11-18 2003-11-18 경구용 소모 필름 조성물

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WO2007125533A3 (fr) * 2006-05-01 2008-02-14 Biota Ltd Films pouvant etre administres par voie orale et leur preparation
US8557274B2 (en) 2005-12-06 2013-10-15 Purdue Research Foundation Slowly digesting starch and fermentable fiber
US9675548B2 (en) 2003-07-24 2017-06-13 GlaxoSmithKline, LLC Orally dissolving films
US10098376B2 (en) 2003-11-07 2018-10-16 U.S. Smokeless Tobacco Company Llc Tobacco compositions
US10945454B2 (en) 2003-11-07 2021-03-16 U.S. Smokeless Tobacco Company Llc Tobacco compositions
US11007144B2 (en) 2016-11-15 2021-05-18 Klaria Pharma Holding Ab Pharmaceutical formulation
SE2050532A1 (en) * 2020-05-07 2021-11-08 Liw Innovation Ab New compositions for oral or nasal use
US11219600B2 (en) 2017-06-08 2022-01-11 Klaria Pharma Holding Ab Pharmaceutical formulation
US12005140B2 (en) 2018-05-23 2024-06-11 Klaria Pharma Holding Ab Pharmaceutical formulation

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KR100855566B1 (ko) * 2006-09-12 2008-09-03 (주) 아모젠 경구용 소모성 필름
KR101074271B1 (ko) * 2009-06-25 2011-10-17 (주)차바이오앤디오스텍 불쾌한 맛을 효과적으로 은폐한 경구용 속용 필름
KR101077468B1 (ko) * 2011-03-04 2011-11-07 (주)차바이오앤디오스텍 안정한 경구용 속용 필름 제제
KR102413426B1 (ko) * 2020-12-21 2022-06-29 주식회사 씨엠지제약 나라트립탄을 포함하는 구강용해 필름 제형

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US10765140B2 (en) 2003-11-07 2020-09-08 U.S. Smokeless Tobacco Company Llc Tobacco compositions
US10945454B2 (en) 2003-11-07 2021-03-16 U.S. Smokeless Tobacco Company Llc Tobacco compositions
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US8840935B2 (en) 2006-05-01 2014-09-23 Biota Ltd. Orally administrable films and preparation thereof
WO2007125533A3 (fr) * 2006-05-01 2008-02-14 Biota Ltd Films pouvant etre administres par voie orale et leur preparation
US11007144B2 (en) 2016-11-15 2021-05-18 Klaria Pharma Holding Ab Pharmaceutical formulation
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CN115515639A (zh) * 2020-05-07 2022-12-23 Liw创新公司 用于口或鼻用的新组合物
SE544672C2 (en) * 2020-05-07 2022-10-11 Liw Innovation Ab New compositions for oral or nasal use
WO2021225509A1 (fr) * 2020-05-07 2021-11-11 Liw Innovation Ab Nouvelles compositions pour utilisation orale ou nasale

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