AU2001229720A1 - Fast dissolving orally consumable films containing an ion exchange resin as a taste masking agent - Google Patents
Fast dissolving orally consumable films containing an ion exchange resin as a taste masking agentInfo
- Publication number
- AU2001229720A1 AU2001229720A1 AU2001229720A AU2001229720A AU2001229720A1 AU 2001229720 A1 AU2001229720 A1 AU 2001229720A1 AU 2001229720 A AU2001229720 A AU 2001229720A AU 2001229720 A AU2001229720 A AU 2001229720A AU 2001229720 A1 AU2001229720 A1 AU 2001229720A1
- Authority
- AU
- Australia
- Prior art keywords
- film according
- ion exchange
- exchange resin
- agent
- consumable film
- 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.)
- Granted
Links
Description
FAST DISSOLVING ORALLY CONSUMABLE FILMS CONTAINING AN ION EXCHANGE RESIN AS A TASTE MASKING AGENT
SPECIFICATION FIELD OF THE INVENTION
This invention relates to fast dissolving orally consumable films containing an agent to mask the taste of a pharmaceutically active agent therein, and more specifically to such films containing an ion exchange resin as the taste masking agent. BACKGROUND OF THE INVENTION
It has been known to administer pharmaceutically active agents in an edible film vehicle.
For example. WO 99/17753 discloses rapidly dissolving films for delivery of drugs to be adsorbed in the digestive tract. WO 98/26780 discloses a flat, foil, paper or wafer type presentation for the application and release of active substances in the buccal cavity. The specific active ingredient disclosed in WO 98/26780 is buprenorphine.
WO 98/20862 discloses a film for use in the oral cavity that can contain a cosmetic or pharmaceutical active substance. WO 98/26763 discloses a flat, foil, paper or wafer like presentation for release of active substances into the buccal cavity. The particular active disclosed is apomorphine.
U.S. Patent Application No. 09/395,104 also discloses the delivery of pharmaceutical agents in a edible film vehicle. U.S. Patent No. 5,41 1 ,945 to Ozaki et al. discloses a pullulan binder and products produced therewith, including edible films (Example B-2). The products can include a variety of ingredients in addition to pullulan, such as other polysaccharides, antibacterial agents, flavor-imparting agents and pharmaceutically active substances (column 4, lines 5-15).
U.S. Patent No. 3,784,390 Hijiya et al. discloses pullulan films and their use in coating and packing materials for foods, pharmaceuticals and other oxygen sensitive materials. All of the examples in this patent teach mixing pullulan in hot water. It has also been known to combine ion exchange resins with pharmaceutically active agents to provide sustained release formulations.
For example, U.S. Patent No. 6,001 ,392 to Wen et al. discloses a controlled-release syrup suspension for oral administration containing dextrometho han adsorbed to a polystyrene sulfonate ion exchange resin. Pharmaceutical films are not disclosed.
U.S. Patent No. 5,980,882 to Eichman discloses a method for improving the stability of a pharmaceutical composition that contains a drug-resin complex, comprising adding a chelating agent in an amount effective to reduce the rate of degradation of the drug in the drug-resin complex. Although Eichman teaches that complexing a drug with an ion exchange resin can mask the taste of the drug. Pharmaceutical films are not disclosed.
The inventors are not aware of any suggestion in the published art that ion exchange resins can act as taste masking agents in a fast dissolving orally consumable film. Accordingly, an object of this invention is to provide fast dissolving orally consumable films containing an ion exchange resin to mask the taste of a pharmaceutically active agent therein.
All references cited herein are incorporated herein by reference in their entireties.
SUMMARY OF THE INVENTION The invention provides a consumable film adapted to adhere to and dissolve in a mouth of a consumer, wherein the film comprises at least one water soluble polymer, at least one pharmaceutically active agent and at least one taste masking agent.
Also provided is a method for preparing the consumable film of the invention, comprising: dissolving water-soluble ingredients in water to provide an aqueous solution; 5 mixing at least one water soluble film former and at least one stabilizing agent to provide a film-forming mixture; combining the film-forming mixture and the aqueous solution to provide a hydrated polymer gel; mixing oils to form an oil mixture; l o adding the oil mixture to the hydrated polymer gel and mixing to provide a uniform gel; casting the uniform gel on a substrate; and drying the cast gel to provide the film.
DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS 15 The invention provides a physiologically acceptable film that is particularly well adapted to adhere to and dissolve in a mouth of a consumer to deliver a pharmaceutically active agent. Preferred films according to the invention comprise a pharmaceutically active agent, an ion exchange resin, a film-forming agent, and at least one of the following additional ingredients: 0 water, antimicrobial agents, plasticizing agents, flavoring agents, saliva stimulating agents, cooling agents, surfactants, stabilizing agents, emulsifying agents, thickening agents, binding agents, coloring agents, sweeteners, fragrances, triglycerides, preservatives, polyethylene oxides, propylene glycol, and the like. 5 The expression "physiologically acceptable" as used herein is intended to encompass compounds, which upon administration to a patient, are adequately tolerated without causing undue negative side effects. The expression encompasses edible compounds.
The expression "pharmaceutically active agents" as used herein is intended to encompass 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 are not particularly limited; however, they should be physiologically acceptable and compatible with the film. Suitable pharmaceutically active agents include, but are not limited to:
A. antimicrobial agents, such as triclosan, cetyl pyridium chloride, domiphen bromide, quaternary ammonium salts, zinc compounds, sanguinarine, fluorides, alexidine, octonidine, EDTA, and the like; B. non-steroidal anti-inflammatory drugs, such as aspirin, acetaminophen, ibuprofen, ketoprofen, diflunisal, fenoprofen calcium, naproxen, tolmetin sodium, indomethacin, and the like;
C. anti-tussives, such as benzonatate, caramiphen edisylate, menthol, dextromethorphan hydrobromide, chlophedianol hydrochloride, and the like;
D. decongestants, such as pseudoephedrine hydrochloride, phenylepherine, phenylpropanolamine, pseudoephedrine sulfate, and the like;
E. anti-histamines, such as brompheniramine maleate, chlorpheniramine maleate, carbinoxamine maleate, clemastine fumarate, dexchlorpheniramine maleate, diphenhydramine hydrochloride, diphenylpyraline hydrochloride, azatadine meleate, diphenhydramine citrate, doxylamine succinate, promethazine hydrochloride, pyrilamine maleate, tripelennamine citrate, triprolidine hydrochloride, acrivastine, loratadine, brompheniramine, dexbrompheniramine, and the like; F. expectorants, such as guaifenesin, ipecac, potassium iodide, terpin hydrate, and the like;
G. anti-diarrheals, such a loperamide, and the like;
H. H2-antagonists, such as famotidine, ranitidine, and the like;
I. proton pump inhibitors, such as omeprazole, lansoprazole, and the like;
J. general nonselective CNS depressants, such as aliphatic alcohols, barbiturates and the like; K. general nonselective CNS stimulants such as caffeine, nicotine, strychnine, picrotoxin, pentylenetetrazol and the like;
L. drugs that selectively modify CNS function, such as phenyhydantoin, phenobarbital, primidone, carbamazepine, ethosuximide, methsuximide, phensuximide, trimethadione, diazepam, benzodiazepines, phenacemide, pheneturide, acetazolamide, sulthiame, bromide, and the like;
M. antiparkinsonism drugs such as levodopa, amantadine and the like;
N. narcotic-analgesics such as morphine, heroin, hydromorphone, metopon, oxymoφhone, levoφhanol, codeine, hydrocodone, xycodone, naloφhine, naloxone, naltrexone and the like;
O. analgesic-antipyretics such as salycilates, phenylbutazone, indomethacin, phenacetin and the like; and P. psychopharmacological drugs such as chloφromazine, methotrimeprazine, haloperidol, clozapine. reseφine, imipramine, tranylcypromine, phenelzine, lithium and the like.
The amount of pharmaceutically active agent that can be used in the rapidly dissolving films, according to the present invention, is dependent upon the dose needed to provide an effective amount of the pharmaceutically active agent. Examples of doses for specific pharmaceutically active agents that can be delivered per one strip of rapidly dissolving oral film are reviewed in Table A.
TABLE A
PHARMACEUTICALLY ACTIVE AGENT PREFERRED DOSE
Chloφheniramine Maleate 4 mg.
Brompheniramine Maleate 4 mg.
Dexchloφheniramine 2 mg.
Dexbrompheniramine 2 mg.
Triprolidine Hydrochloride 2.5 mg.
Acrivastine 8 mg.
Azatadine Maleate 1 mg.
Loratidine 10 mg.
Phenylephrine Hydrochloride 10 mg.
Dextromethoφhan Hydrobromide 10-30 mg.
Ketoprofen 12.5-25 mg.
Sumatriptan Succinate 35 - 70 mg.
Zolmitriptan 2.5 mg.
Loperamide 2 mg.
Famotidine 10 mg.
Nicotine 2 mg.
Diphenhydramine Hydrochloride 12.5-25 mg.
Pseudoephedrine Hydrochloride 30 mg.
Ion exchange resins preferred for use in the films of the invention are water-insoluble and consist of a pharmacologically inert organic or inorganic matrix containing covalently bound functional groups that are ionic or capable of being ionized under the appropriate conditions of pH. The organic matrix may be synthetic (e.g., polymers or copolymers of acrylic acid, methacrylic acid, sulfonated styrene, sulfonated divinylbenzene), or partially synthetic (e.g., modified cellulose and dextrans). The inorganic matrix can also be, e.g., silica gel modified by the addition of ionic groups. The covalently bound ionic groups may be strongly acidic (e.g., sulfonic acid), weakly acidic (e.g., carboxylic acid), strongly basic (e.g., quaternary ammonium), weakly basic (e.g., primary amine), or a combination of acidic and basic groups. In general, those types of ion exchangers suitable for use in ion exchange chromatography and for such applications as deionization of water are suitable for use in these
controlled release drug preparations. Such ion exchangers are described by H. F. Walton in "Principles of Ion Exchange" (pp. 312-343). The ion exchange resins useful in the present invention have exchange capacities below about 6 milliequivalents per gram (meq/g) and preferably below about 5.5 meq/g. The resin is crosslinked with a crosslinking agent selected from difunctional compounds capable of crosslinking polystyrenes; these are commonly known in the art. Preferably, the crosslinking agent is a divinyl or polyvinyl compound. Most preferably the crosslinking agent is divinylbenzene. The resin is crosslinked to an extent of about 3 to about 20%, preferably about 4 to about 16%, more preferably about 6 to about 10%, and most preferably about 8% by weight based on the total resin. The resin is crosslinked with the crosslinking agent by means well known in the art.
The size of the ion exchange resins should preferably fall within the range of about 20 to about 200 micrometers. Particle sizes substantially below the lower limit are difficult to handle in all steps of the processing. Particle sizes substantially above the upper limit, e.g., commercially available ion exchange resins having a spherical shape and diameters up to about 1000 micrometers, are gritty in liquid dosage forms and have a greater tendency to fracture when subjected to drying-hydrating cycles. Representative resins useful in this invention include AMBERLITE
IRP-69 (obtained from Rohm and Haas) and Dow XYS-40010.00 (obtained from The Dow Chemical Company). Both are sulfonated polymers composed of polystyrene cross-linked with 8% of divinylbenzene, with an ion exchange capacity of about 4.5 to 5.5 meq/g of dry resin (H+-form). Their essential difference is in physical form. AMBERLITE IRP-69 comprises irregularly-shaped particles with a size range of 47 to 149 micrometers, produced by milling the parent, large-sized spheres of AMBERLITE IRP-120. The Dow XYS-40010.00 product comprises spherical particles with a size
range of 45 to 150 micrometers. Another useful exchange resin, Dow XYS-40013.00, is a polymer composed of polystyrene cross-linked with 8% of divinylbenzene and functionalized with a quaternary ammonium group; its exchange capacity is normally within the range of approximately 3 to 4 meq/g of dry resin.
The most preferred resin is AMBERLITE IRP-69. However, in less preferred embodiments, the taste masking agent need not be an ion exchange resin. In these embodiments, the taste masking agent can be, e.g., magnesium trisilicate. See, e.g., U.S. Patents Nos. 4,650,663 and 4,581,232 to Peters et al. Taste can also be masked by polymers, such as EUDRAGIT E (Rohm and Haas), and/or cellulosics, such as ethylcellulose, and the like.
The film-forming agent used in the films according to the present invention can be selected from the group consisting of pullulan, hydroxypropylmethyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, polyvinyl pyrrolidone, carboxymethyl cellulose, polyvinyl alcohol, sodium alginate, polyethylene glycol, xanthan gum, tragacanth gum, guar gum, acacia gum, arabic gum, polyacrylic acid, methylmethacrylate copolymer, carboxyvinyl polymer, amylose, high amylose starch, hydroxypropylated high amylose starch, dextrin, pectin, chitin, chitosan, levan, elsinan, collagen, gelatin, zein, gluten, soy protein isolate, whey protein isolate, casein and mixtures thereof. A preferred film former is pullulan, in amounts ranging from about 0.01 to about 99 wt%, preferably about 30 to about 80 wt%, more preferably from about 45 to about 70 wt% of the film and even more preferably from about 60 to about 65 wt% of the film. Unless specified otherwise, the term "wt%" as used herein with reference to the final product (i.e., the film, as opposed to the formulation used to create it), denotes the percentage of the total dry weight contributed by the subject ingredient. This theoretical value can differ from the experimental
value, because in practice, the film typically retains some of the water and/or ethanol used in preparation.
In embodiments containing relatively high oil content, it is preferable to avoid substantial amounts of humectant in the film (and more preferable to have no humectant in the film), so as to avoid producing an overly moist, self- adhering film. In particular, it is preferred to formulate high oil content films with a plasticizing agent other than glycerin, which is also a humectant, and with a sweetener other than sorbitol, which is a mild humectant.
Saliva stimulating agents can also be added to the films according to the present invention. Useful saliva stimulating agents are those disclosed in U.S. Patent No. 4,820,506. Saliva stimulating agents include food acids such as citric, lactic, malic, succinic, ascorbic, adipic, fumaric and tartaric acids. Preferred food acids are citric, malic and ascorbic acids. The amount of saliva stimulating agents in the film is from about 0.01 to about 12 wt%, preferably about 1 wt% to about 10 wt%, even more preferably about 2.5 wt% to about 6 wt%.
Preferred plasticizing agents include triacetin in amounts ranging from about 0 to about 20 wt%, preferably about 0 to about 2 wt%. Other suitable plasticizing agents include monoacetin and diacetin. Preferred cooling agents include monomenthyl succinate, in amounts ranging from about 0.001 to about 2.0 wt%, preferably about 0.2 to about 0.4 wt%. A monomenthyl succinate containing cooling agent is available from Mane, Inc. Other suitable cooling agents include WS3, WS23, Ultracool II and the like. Preferred surfactants include mono and diglycerides of fatty acids and poly oxyethylene sorbitol esters, such as, Atmos 300 and Polysorbate 80. The surfactant can be added in amounts ranging from about 0.5 to about 15 wt%, preferably about 1 to about 5 wt% of the film. Other suitable surfactants
include pluronic acid, sodium lauryl sulfate, and the like.
Preferred stabilizing agents include xanthan gum, locust bean gum and carrageenan, in amounts ranging from about 0 to about 10 wt%, preferably about 0.1 to about 2 wt% of the film. Other suitable stabilizing agents include guar gum and the like.
Preferred emulsifying agents include triethanolamine stearate, quaternary ammonium compounds, acacia, gelatin, lecithin, bentonite, veegum, and the like, in amounts ranging from about 0 to about 5 wt%, preferably about 0.01 to about 0.7 wt% of the film. Preferred thickening agents include methylcellulose, carboxyl mefhylcellulose, and the like, in amounts ranging from about 0 to about 20 wt%, preferably about 0.01 to about 5 wt%.
Preferred binding agents include starch, in amounts ranging from about 0 to about 10 wt%, preferably about 0.01 to about 2 wt% of the film. Suitable sweeteners that can be included are those well known in the art, including both natural and artificial sweeteners. Suitable sweeteners include, e.g.:
A. water-soluble sweetening agents such as monosaccharides, disaccharides and polysaccharides such as xylose, ribose, glucose (dextrose), mannose, galactose, fructose (levulose), sucrose (sugar), maltose, invert sugar (a mixture of fructose and glucose derived from sucrose), partially hydrolyzed starch, corn syrup solids, dihydrochalcones, monellin, steviosides, and glycyrrhizin;
B. 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-6-methyl-l,2,3-oxathiazine- 4-one-2, 2-dioxide, the potassium salt of 3,4-dihydro-6-methyl-l,2,3- oxathiazine-4-one-2,2-dioxide (acesulfame-K), the free acid form of saccharin,
and the like;
C. dipeptide based sweeteners, such as L-aspartic acid derived sweeteners, such as L-aspartyl-L-phenylalanine methyl ester (aspartame) and materials described in U.S. Pat. No. 3,492,131, L- alpha- aspartyl-N-(2,2,4,4~tetramethyl-3-thietanyl)-D-alaninamide hydrate, methyl esters of L-aspartyl-L-phenylglycerin and L-aspartyl-L-2,5,dihydrophenyl- glycine, L-aspartyl-2,5-dihydro- L-phenylalanine, L-aspartyl-L-( 1 - cyclohexyen)-alanine, and the like;
D. water-soluble sweeteners derived from naturally occurring water-soluble sweeteners, such as a chlorinated derivative of ordinary sugar
(sucrose), known, for example, under the product description of sucralose; and
E. protein based sweeteners such as thaumatoccous danielli (Thaumatin I and II).
In general, an effective amount of auxiliary sweetener is utilized to provide the level of sweetness desired for a particular composition, and this amount will vary with the sweetener selected. This amount will normally be 0.01 % to about 10 % by weight of the composition when using an easily extractable sweetener. The water-soluble sweeteners described in category A above, are usually used in amounts of about 0.01 to about 10 wt%, and preferably in amounts of about 2 to about 5 wt%. Some of the sweeteners in category A (e.g., glycyrrhizin) can be used in amounts set forth for categories B-E below due to the sweeteners' known sweetening ability. In contrast, the sweeteners described in categories B-E are generally used in amounts of about 0.01 to about 10 wf%, with about 2 to about 8 wt% being preferred and about 3 to about 6 wt% being most preferred. These amounts may be used to achieve a desired level of sweetness independent from the flavor level achieved from any optional flavor oils used. Of course, sweeteners need not be added to films intended for non-oral administration.
The flavorings that can be used include those known to the skilled artisan, such as natural and artificial flavors. These flavorings may be chosen from synthetic flavor oils and flavoring aromatics, and/or oils, oleo resins and extracts derived from plants, leaves, flowers, fruits and so forth, 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. Also useful are artificial, natural or synthetic fruit flavors 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 so forth. These flavorings can be used individually or in admixture. Commonly used flavors include mints such as peppermint, artificial vanilla, cinnamon derivatives, and various fruit flavors, whether employed individually or in admixture. Flavorings such as aldehydes and esters including cinnamyl acetate, cinnamaldehyde, citral, diethylacetal, dihydrocarvyl acetate, eugenyl formate, p-methylanisole, and so forth may also be used. Generally, any flavoring 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. Further examples of aldehyde flavorings include, but are not limited to acetaldehyde (apple); benzaldehyde (cherry, almond); cinnamic aldehyde (cinnamon); citral, i.e., alpha citral (lemon, lime); neral, i.e. beta citral (lemon, lime); decanal (orange, lemon); ethyl vanillin (vanilla, cream); heliotropine, i.e., piperonal (vanilla, cream); vanillin (vanilla, cream); alpha- amyl cinnamaldehyde (spicy fruity flavors); butyraldehyde (butter, cheese); valeraldehyde (butter, cheese); citronellal (modifies, many types); decanal (citrus fruits); aldehyde C-8 (citrus fruits); aldehyde C-9 (citrus fruits); aldehyde C-12 (citrus fruits); 2-ethyl butyraldehyde (berry fruits); hexenal, i.e. trans-2 (berry fruits); tolyl aldehyde (cherry, almond); veratraldehyde (vanilla);
2,6-dimethyl- 5-heptenal, i.e. melonal (melon); 2-6-dimethyloctanal (green fruit); and 2-dodecenal (citrus, mandarin); cherry; grape; mixtures thereof; and the like.
The amount of flavoring employed is normally a matter of preference subject to such factors as flavor type, individual flavor, and strength desired. Thus, the amount may be varied in order to obtain the result desired in the final product. Such variations are within the capabilities of those skilled in the art without the need for undue experimentation. In general, amounts of about 0.1 to about 30 wt% are useable with amounts of about 2 to about 25 wt% being preferred and amounts from about 8 to about 10 wt% are more preferred.
The compositions of this invention can also contain coloring agents or colorants. The coloring agents are used in amounts effective to produce the desired color. The coloring agents useful in the present invention, include pigments such as titanium dioxide, which may be incoφorated in amounts of up to about 5 wt%, and preferably less than about 1 wf%. Colorants can also include natural food colors and dyes suitable for food, drug and cosmetic applications. These colorants are known as FD&C dyes and lakes. The materials acceptable for the foregoing spectrum of use are preferably water- soluble, and include FD&C Blue No. 2, which is the disodium salt of 5,5- indigotindisulfonic acid. Similarly, the dye known as Green No. 3 comprises a triphenylmethane dye and is the monosodium salt of 4-[4-N-ethyl-p- sulfobenzylamino) diphenyl-methylene]-[ 1 -N-ethyl-N-p-sulfonium benzyl)- 2,5-cyclo-hexadienimine]. A full recitation of all FD&C and D&C dyes and their corresponding chemical structures may be found in the Kirk-Othmer Encyclopedia of Chemical Technology, Volume 5, Pages 857-884, which text is accordingly incoφorated herein by reference.
The films can also include a triglyceride. Examples of triglycerides include vegetable oils such as corn oil, sunflower oil, peanut oil, olive oil,
canola oil, soybean oil and mixtures thereof. A preferred triglyceride is olive oil. The triglyceride is added to the film in amounts from about 0.1 wt% to about 12 wf%, preferably in a range from about 0.5 wt% to about 9 wt%, of the film. The films can include a preservative in amounts from about 0.001 wt% to about 5 wt%, preferably from about 0.01 wt% to about 1 wt% of the film. Preferred preservatives include sodium benzoate and potassium sorbate. Other suitable preservatives include, but are not limited to, salts of edetate (also known as salts of ethylenediaminetetraacetic acid, or EDTA, such as disodium EDTA) and parabens (e.g., methyl, ethyl, propyl or butyl-hydroxybenzoates, etc.) or sorbic acid. The preservatives listed above are exemplary, but each preservative must be evaluated on an empirical basis, in each formulation, to assure the compatibility and efficacy of the preservative. Methods for evaluating the efficacy of preservatives in pharmaceutical formulations are known to those skilled in the art.
The films can also include a polyethylene oxide compound. The molecular weight of the polyethylene oxide compound ranges from about 50,000 to about 6,000,000. A preferred polyethylene oxide compound is N-10 available from Union Carbide Coφoration. The polyethylene oxide compound is added in amounts from about 0.1 wt% to about 5 wt%, preferably from about
0.2 wt% to about 4.0 wf% of the film.
The films can also include propylene glycol. The propylene glycol is added in amounts from about 1 wt% to about 20 wt%, preferably from about 5 wt% to about 15 wt% of the film. Methods for preparing films according to the invention are capable of encapsulating the oil ingredients within the film-forming matrix and maintaining the integrity of the film, even when the film contains oils in amounts of 10 wt% or more.
In certain methods for preparing films according to the invention, the film-forming ingredients are mixed and hydrated with water separately from the water-soluble ingredients, which are mixed in aqueous solution separately from the organic ingredients and surfactants. In these methods, the final formulation is preferably produced by mixing the film-forming phase with the aqueous phase, then mixing in the organic phase, which includes surfactants, such as Polysorbate 80 and Atmos 300. This mass is mixed until emulsified. In other embodiments, the aqueous and film forming phases are combined into a single phase by dissolving the water soluble ingredients in the water and then adding the gums to hydrate. The organic phase is then added to this single aqueous phase.
The resulting formulation is cast on a suitable substrate and dried to form a film. The film is preferably air-dried or dried under warm air and cut to a desired dimension, packaged and stored. The film can contain from about 0.1% to about 10 wt% moisture, preferably from about 3 % to about 8 wt% moisture, even more preferably from about 4 to about 7 wt% moisture.
The film-forming phase can include pullulan and stabilizing agents such as xanthan gum, locust bean gum and carrageenan. These ingredients are mixed and then hydrated in water for about 30 to about 48 hours to form a gel. The water is preferably heated to a temperature of about 25 to about 45°C to promote hydrati on. The amount of water is about 40 to 80% of the gel. The resulting hydrated gel is then chilled to a temperature of about 20 to about 30°C for about 1 to about 48 hours. The water is preferably deionized.
In preferred embodiments, the aqueous phase includes water heated to a temperature of about 60 to 90°C, preferably 70 to 80°C, and ingredients such as the pharmaceutically active agent, ion exchange resin (or other masking agent), coloring agent, preservative and sweetener. The water is preferably deionized and the amount of water used is about 5 to about 80 wt% of the final gel
mixture.
The pharmaceutically active agent is sorbed to the ion exchange resin (or other masking agent) without separating ion exchanged pharmaceutically active agent from unexchanged agent and counter ion salts. Adsoφtion of the pharmaceutically active agent onto the ion exchange resin particles to form the pharmaceutically active agent/resin complex is a well known technique as shown in U.S. Pat. Nos. 2,990,332 and 4,221,778. In general, the pharmaceutically active agent is mixed with an aqueous suspension of the resin, and in less preferred embodiments, the complex is then washed and dried. Adsoφtion of pharmaceutically active agent onto the resin may be detected by measuring a change in the pH of the reaction medium, or by measuring a change in concentration of sodium or pharmaceutically active agent.
Binding of pharmaceutically active agent to resin can be accomplished according to four general reactions. In the case of a basic pharmaceutically active agent, these are: (a) resin (Na-form) plus pharmaceutically active agent (salt form); (b) resin (Na-form) plus pharmaceutically active agent (as free base); (c) resin (H-form) plus pharmaceutically active agent (salt form); and (d) resin (H-form) plus pharmaceutically active agent (as free base). All of these reactions except (d) have cationic byproducts, by competing with the cationic pharmaceutically active agent for binding sites on the resin, reduce the amount of pharmaceutically active agent bound at equilibrium. For basic pharmaceutically active agents, stoichiometric binding of pharmaceutically active agent to resin is accomplished only through reaction (d). Four analogous binding reactions can be carried out for binding an acidic pharmaceutically active agent to an anion exchange resin. These are: (a) resin (Cl~form) plus pharmaceutically active agent (salt form); (b) resin (Cl—form) plus pharmaceutically active agent (as free acid); (c) resin
(OH—form) plus pharmaceutically active agent (salt form); and (d) resin (OH~form) plus pharmaceutically active agent (as free acid). All of these reactions except (d) have ionic by-products and the anions generated when the reactions occur compete with the anionic pharmaceutically active agent for binding sites on the resin with the result that reduced levels of pharmaceutically active agent are bound at equilibrium. For acidic pharmaceutically active agents, stoichiometric binding of pharmaceutically active agent to resin is accomplished only through reaction (d). The binding may be performed, for example, as a batch or column process, as is known in the art. In less preferred embodiments, the adsoφtion complex, including pharmaceutically active agent and resin, is collected and washed with ethanol and/or water to insure removal of any unadsorbed pharmaceutically active agent. The complexes are usually air-dried in trays at room or elevated temperature. The ratio of the pharmaceutically active agent adsorbate to ion exchange resin adsorbent in the adsoφtion complex is about 1 :3 to about 3: 1 , preferably about 1 :2 to about 2: 1, most preferably about 1 : 1. The only limit to using ratios in excess of 1 :3 is an economic and aesthetic one.
The amount of the pharmaceutically active agent adsorbed to the ion exchange resin is in the range from about 25 to about 75% by weight of the pharmaceutically active agent/resin adsoφtion complex (hereinafter referred to as the "pharmaceutically active agent/resin complex'" or "complex"). More preferably, the amount of the pharmaceutically active agent adsorbed to the ion exchange resin is in the range from about 33 to about 77% by weight of the pharmaceutically active agent/resin complex. Most preferably, the amount of the pharmaceutically active agent adsorbed to the ion exchange resin is in the range from about 40 to about 60% by weight of the pharmaceutically active agent/resin complex.
The amount of pharmaceutically active agent/resin complex in the formulation is adjusted to deliver a predetermined dose of the pharmaceutically active agent over a predetermined period of time.
For example, a preferred antitussive film of the invention is administered at one dose every 12 hours to deliver a pharmaceutically effective amount of dextromethoφhan over a period of approximately 12 hours to a patient in need of such administration. A typical adult dose of a film of the invention measuring 1 " x 1.25" (2.54 cm x 3.18 cm) weighs about 60 to about 190 mg and contains about 20 to about 130 mg of pharmaceutically active agent/resin complex to deliver about 5 to about 65 mg of pharmaceutically active agent (e.g., dextromethoφhan hydrobromide) when the average pharmaceutically active agent:ion exchange resin ratio is about 1 :1.
In a particularly preferred embodiment of the invention, pullulan is present in the film in an amount of about 2 to about 6 mg/cm , dextromethoφhan is present in the film in an amount of about 1.4 to about 3 mg/cm , and sulfonated polymer ion exchange resin is present in said film in an amount of about 1.4 to about 2 mg/cm2.
The antitussive pharmaceutically active agents that are suitable for use in these preparations are acidic, amphoteric or most often basic antitussives. Examples of basic pharmaceutically active agents useful in the present invention include, but are not limited to dextromethoφhan, diphenhydramine, caramiphen, carbapentane, ethylmoφhine, noscapine and codeine. In addition, the antitussive embodiments of the invention can further comprise additional agents that are therapeutically effective to treat conditions other than coughing. That is, more than one type of pharmaceutically active agent can be included in a film of the invention. For example, in the case of a film containing an antitussive agent, the film can further comprise an antihistamine, sympathomimetic pharmaceutically active agent (nasal decongestant,
bronchodilator), analgesic, antiinflammatory, cough suppressant and/or expectorant. Compounds which are antihistamines, sympathomimetic pharmaceutically active agents (nasal decongestant, bronchodilator), analgesic, antiinflammatory, cough suppressants and/or expectorants are well known to those of skill in the art and need not be discussed in detail herein.
In embodiments, a certain percentage of the films disclosed herein will contain non-coated pharmaceutically active agent/resin complexes. The remaining pharmaceutically active agent/resin complexes are further characterized by the presence of a coating. In the preferred embodiment of the present invention, about 20 to about 80% of the pharmaceutically active agent/resin complexes in the sustained-release compositions are coated, most preferably about 40 to about 60% of the pharmaceutically active agent/resin complexes. The coating is a water-permeable, diffusion barrier coating material. The presence of a coating allows one to selectively modify the dissolution profile as desired of a pharmaceutical composition comprising the pharmaceutically active agent/resin complexes of the present invention. The coating materials can in general be any of a large number of conventional natural or synthetic film-forming materials used singly, in admixture with each other, and in admixture with plasticizers, pigments, etc. with diffusion barrier properties and with no inherent pharmacological or toxic properties. In general, the major components of the coating should be insoluble in water, and permeable to water and pharmaceutically active agent. However, it might be desirable to incoφorate a water-soluble substance, such as methyl cellulose, to alter the permeability of the coating, or to incoφorate an acid-insoluble, base-soluble substance to act as an enteric coating. The coating materials may be applied as a suspension in an aqueous fluid or as a solution in organic solvents. Suitable examples of such coating materials are described by R. C. Rowe in Materials used in Pharmaceutical Formulation. (A. T. Florence,
editor), Blackwell Scientific Publications, Oxford, 1-36(1984), incoφorated by reference herein. Preferably the water-permeable diffusion barrier is selected from the group consisting of ethyl cellulose, methyl cellulose and mixtures thereof Most preferably, the coating material is SURELEASE, manufactured by Colorcon which is water based ethyl cellulose latex, plasticized with dibutyl sebacate or with vegetable oils. Other non-limiting coating materials included within the scope of the present invention are AQUACOAT, manufactured by FMC Corporation of Philadelphia, which is ethylcellulose pseudolatex; solvent based ethylcellulose; shellac; zein; rosin esters; cellulose acetate; EUDRAGITS, manufactured by Rohm and Haas of Philadelphia, which are acrylic resins; silicone elastomers; poly( vinyl chloride) methyl cellulose; and hydroxypropylmethyl cellulose.
Conventional coating solvents and coating procedures (such as fluid bed coating and spray coating) can be employed to coat the particles. Techniques of fluid bed coating are taught, for example, in U.S. Patents Nos. 3,089,824, 3,1 17,027, and 3,253,944. The coating is normally applied to the pharmaceutically active agent/resin complex, but alternatively can be applied to the resin before complexing with the pharmaceutically active agent. Non-limiting examples of coating solvents include ethanol, a methylene chloride/acetone mixture, coating emulsions, methyl acetone, tetrahydrofuran, carbonetetrachloride, methyl ethyl ketone, ethylene dichloride, trichloroethylene, hexane, methyl alcohol, isopropyl alcohol, methyl isobutyl ketone, toluene, 2-nitropropane, xylene, isobutyl alcohol, n-butyl acetate. It is preferred that the coated pharmaceutically active agent/resin complexes are coated in the range from about 40 to about 70% w/w pharmaceutically active agent/resin complex. More preferably, the pharmaceutically active agent/resin complex is coated in the range from about 45 to about 55% w/w pharmaceutically active agent/resin complex. Most
preferably, the pharmaceutically active agent/resin complex is coated about 50% w/w pharmaceutically active agent/resin complex. Variation in the amount of coating and/or the use of coated/uncoated complex mixtures can be employed to selectively modify the dissolution profile as desired. The average particle sizes of the non-hydrated coated and uncoated pharmaceutically active agent/resin complexes is about 60 to about 200 and about 60 to about 250 micrometers, respectively. More preferably, average particle sizes of the coated pharmaceutically active agent/resin complexes is between about 70 and about 190 micrometers, and most preferably about 70 to about 180 micrometers. More preferably, average particle sizes of the uncoated pharmaceutically active agent/resin complexes is between about 55 and about 160 micrometers, and most preferably about 60 to about 150 micrometers. It is desirable that about 85%, preferably about 95%, and most preferably about 98% of the resin particles have sizes within the ranges set forth above. Adjustments within these ranges can be made to accommodate desired aesthetic qualities of the final formulation product. It is more preferable that the resin dextromethoφhan complex have particle sizes within these ranges as well.
In embodiments, it is possible to hydrate the film-forming ingredients and combine all of the ingredients without heating. This method comprises dissolving the water-soluble ingredients in water to form an aqueous mixture; mixing the film-forming ingredients in powder form to form a powder mixture; adding the powder mixture to the aqueous mixture to form a hydrated polymer gel; stirring the hydrated polymer at room temperature for about 30 minutes to about 48 hours; mixing the cooling agent, menthol and any other oils to form an oil mixture; adding the oil mixture to the hydrated polymer gel and mixing until uniform; deaerating the film until air bubbles are removed, casting the uniform mixture on a suitable substrate; and drying the cast mixture to form a
film. This method hydrates the film-forming ingredients without heating the water, which can reduce energy costs in the manufacturing process and undesirable losses of volatile ingredients to evaporation. Further, mixing the oils in two steps minimizes the amount of flavor lost. While not wishing to be bound by any theories, it is believed that the film-forming ingredients can be hydrated and mixed without heating due to an ionic effect known as the Donnan equilibrium. Hydrating the film-forming agents in the presence of electrolytes in solution effectively lowers the viscosity of the polymer gel being formed, thus increasing the efficiency of the hydrating process. The water-soluble ingredients of the formulation provide the electrolytes, which are dissolved in the hydration solution prior to addition of the film- forming ingredients. High-shear mixing also accelerates hydration, which delumps the powders, providing greater surface area for water contact. In addition, local heating effects, generated in the shear regions, provide energy for hydration without substantially raising the temperature of the mass.
Examples
The invention will be illustrated in more detail with reference to the following Examples, but it should be understood that the present invention is not deemed to be limited thereto. Example 1
The ingredients listed in Table 1 were combined to provide a comparative example of an antitussive film in accordance with the following procedure:
A. The water was heated to 50°C. The potassium sorbate and sweeteners were dissolved in the water with mixing. The titanium dioxide was then added with further mixing to form Preparation A.
B. The film-forming ingredients (e.g., xanthan gum, locust bean gum, carrageenan and pullulan) were mixed in a separate container to form
Preparation B.
C. Preparation B was slowly added to Preparation A with rapid mixing, followed by overnight mixing at a reduced rate to provide Preparation C. D. The glycerin and olive oil were combined in a separate container and then the menthol and monoammonium glycyrrhizinate (MAG) were dissolved therein by heating to 45°C to form Preparation D.
E. Preparation D was added to Preparation C with thorough mixing and then the flavor agents were added with continued mixing to provide Preparation E.
F. Dextromethoφhan coated with ethyl cellulose was then added to Preparation E with mixing. The pH was adjusted as necessary to 6.0 using 10% citric acid solution to provide Preparation F (Examples 1-3 only).
Preparation F was poured on a mold and cast to form a film of a desired thickness at room temperature. The film was dried under warm air and cut to a desired dimension (dictated by, e.g., dosage and mouthfeel) for taste testing.
The film was segmented into 1 " x 1.25" (2.54 cm x 3.18 cm) dosage units, each of which had a thickness of 0.009±0.002 in (0.23±0.05 mm) and a weight of
70±3 mg. A placebo film was also prepared in accordance with the foregoing to facilitate evaluation of, e.g., the taste and appearance of the active film.
Table 1
The active film was gritty and bitter.
Example 2
Comparative films having the ingredients listed in Table 2 were prepared in accordance with the method of Example 1.
Table 2
The active film was gritty and bitter.
Example 3
Comparative films having the ingredients listed in Table 3 were prepared in accordance with the method of Example 1.
Table 3
The active film was very thin, blue and gritty. Sensations of bitterness and numbness were minimal, but the flavor was not entirely agreeable. Example 4
Films of the invention having the ingredients listed in Table 4 were prepared in accordance with the method of Example 1 , except that Step F comprised adding uncoated dextromethoφhan hydrobromide and AMBERLITE resin to Preparation E as separate ingredients.
Table 4
The active film had a pleasing appearance and taste. Example 5
The ingredients listed in Table 5 were combined to provide an example of an antitussive film of the invention in accordance with the following procedure:
A. The water was heated to 75°C. Uncoated dextromethoφhan hydrobromide was dissolved with mixing in the water, while maintaining the temperature at 75°C. AMBERLITE resin was then mixed into the water with heating for 4 to 5 hours at 70-80°C. Heating was stopped, water lost to evaporation was replaced, and the potassium sorbate and sweeteners were then added to the composition with mixing to form Preparation A. B. The film-forming ingredients (e.g., xanthan gum, locust bean gum, carrageenan and pullulan) were mixed in a separate container to form Preparation B.
C. Preparation B was slowly added to Preparation A with rapid mixing, followed by overnight mixing at a reduced rate to provide Preparation C.
D. The menthol was dissolved with mixing in the alcohol in a separate container. The Physcool was then dissolved with mixing therein. The MAG, Polysorbate 80, Atmos 300 and flavors were then added to the mixture and mixed to enhanced uniformity to form Preparation D. E. Preparation D, glycerine and mannitol were added to
Preparation C with thorough mixing to provide Preparation E.
Preparation E was poured on a mold and cast to form a film of a desired thickness at room temperature. The film was dried under warm air and cut to a desired dimension (dictated by, e.g., dosage and mouthfeel) for taste testing. The film was segmented into 1.5 in (9.7 cm ) dosage units, each of which had a thickness of 0.009±0.002 in (0.23±0.05 mm) and a weight of 70±3 mg.
A placebo film was also prepared in accordance with the foregoing to facilitate evaluation of, e.g., the taste and appearance of the active film.
The active film had a pleasing appearance and taste. Example 6
Films of the invention having the ingredients listed in Table 6 were prepared in accordance with the method of Example 5.
Table 6
The active film had a pleasing appearance and taste. Example 7
A film of the invention having the ingredients listed in Table 7 were
prepared in accordance with the method of Example 5. The film was segmented into 1 " x 1.25" (2.54 cm x 3.18 cm) dosage units, each of which had a thickness of 0.009±0.002 in (0.23±0.05 mm) and a weight of 63.6±3 mg.
Table 7
The active film had a pleasing appearance and taste.
While the invention has been described in detail and with reference to specific examples thereof, it will be apparent to one skilled in the art that various changes and modifications can be made therein without departing from the spirit and scope thereof.
Claims (27)
1. A consumable film adapted to adhere to and dissolve in a mouth of a consumer, wherein said film comprises at least one water soluble polymer, at least one pharmaceutically active agent and at least one taste masking agent.
2. The consumable film according to claim 1, wherein said at least one water soluble polymer is a member selected from the group consisting of pullulan, hydroxyproplymethyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, polyvinyl pyrrolidone, carboxymethyl cellulose, polyvinyl alcohol, sodium alginate, polyethylene glycol, tragacanth gum, guar gum, acacia gum, arabic gum, polyacrylic acid, methylmethacrylate copolymer, carboxyvinyl polymer, amylose, high amylose starch, hydroxypropylated high amylose starch, dextrin, pectin, chitin, chitosan, levan, elsinan, collagen, gelatin, zein, gluten, soy protein isolate, whey protein isolate, casein and mixtures thereof.
3. The consumable film according to claim 2, wherein said at least one water soluble polymer is pullulan.
4. The consumable film according to claim 1, wherein said at least one pharmaceutically active agent is a member selected from the group consisting of antimicrobial agents, non-steroidal anti-inflammatory agents, antitussives, decongestants, anti-histamines, expectorants, anti-diaherrals, H2- antagonists, proton pump inhibitors, central nervous system agents, analgesics and mixtures thereof.
5. The consumable film according to claim 4, wherein the antimicrobial agent is a member selected from the group consisting of triclosan, cetyl pyridium chloride, domiphen bromide, quaternary ammonium salts, zinc compounds, sanguinarine, fluorides, alexidine, octonidine, EDTA and mixtures thereof.
6. The consumable film according to claim 4, wherein the non- steroidal anti-inflammatory agent is a member selected from the group consisting of aspirin, acetaminophen, ibuprofen, diflunisal, fenoprofen calcium, naproxen, tolmetin sodium, indomethacin, and mixtures thereof.
7. The consumable film according to claim 4, wherein the antitussive is a member selected from the group consisting of benzonatate, caramiphen edisylate, dextromethoφhan, chlophedianol, diphenhydramine, salts thereof and mixtures thereof.
8. The consumable film according to claim 4, wherein the decongestant is selected from the group consisting of pseudoephedrine, phenylepherine, phenylpropanolamine, salts thereof and mixtures thereof.
9. The consumable film according to claim 4, wherein the anti- histamine is selected from the group consisting of brompheniramine maleate, chloφheniramine maleate, carbinoxamine maleate, clemastine fumarate, dexchloφheniramine maleate, diphenhydramine hydrochloride, diphenhydramine citrate, diphenylpyraline hydrochloride, doxylamine succinate, promethazine hydrochloride, pyrilamine maleate, tripelennamine citrate, triprolidine hydrochloride and mixtures thereof.
10. The consumable film according to claim 4, wherein the expectorant is selected from the group consisting of guaifenesin, ipecac, potassium iodide, teφin hydrate and mixtures thereof.
1 1. The consumable film according to claim 4, wherein the anti- diarrheal is loperamide.
12. The consumable film according to claim 4, wherein the H2-antagonist is selected from the group consisting of famotidine, ranitidine and mixtures thereof.
13. The consumable film according to claim 4, wherein the proton pump inhibitor is selected from the group consisting of omeprazole, lansoprazole, and mixtures thereof.
14. The consumable film according to claim 1, wherein the at least one taste masking agent is an ion exchange resin.
15. The consumable film according to claim 14, wherein the ion
5 exchange resin is a sulfonated polymer comprising polystyrene cross-linked with divinylbenzene.
16. The consumable film according to claim 14, wherein the ion exchange resin is a sulfonated polymer comprising polystyrene cross-linked with 8% of divinylbenzene, with an ion exchange capacity of about 4.5 to 5.5 l o meq/g of dry resin (H+-form).
17. The consumable film according to claim 16, wherein the ion exchange resin has irregularly-shaped particles ranging in size from about 47 to about 149 micrometers.
18. The consumable film according to claim 16, wherein the ion 15 exchange resin has spherical particles ranging in size from about 45 to about
150 micrometers.
19. The consumable film according to claim 14, wherein the ion exchange resin is a polymer composed of polystyrene cross-linked with 8% of divinylbenzene and functionalized with a quaternary ammonium group, and 0 wherein an exchange capacity of said ion exchange resin is normally within a range of about 3 to about 4 meq/g of dry ion exchange resin.
20. The consumable film according to claim 1, wherein the at least one taste masking agent is magnesium trisilicate.
21. The consumable film according to claim 1 , wherein said at least 5 one water soluble polymer is pullulan, said at least one pharmaceutically active agent is dextromethoφhan, and said at least one taste masking agent is a sulfonated polymer ion exchange resin comprising polystyrene cross-linked with divinylbenzene.
22. The consumable film according to claim 21, wherein said pullulan is present in an amount of about 40 to about 80 wt% of said film, said dextromethoφhan is present in an amount of about 5 to about 40 wt% of said film, said sulfonated polymer ion exchange resin is present in an amount of about 5 to about 40 wt% of said film, and a ratio of said dextromethoφhan to said sulfonated polymer ion exchange resin is 1 :3 to 3: 1.
23. The consumable film according to claim 22, wherein said pullulan is present in said film in an amount of about 2 to about 6 mg/cm , said dextromethoφhan is present in said film in an amount of about 1.4 to about 2 mg/cm , and said sulfonated polymer ion exchange resin is present in said film in an amount of about 1.4 to about 2 mg/cm2.
24. The consumable film according to claim 22, further comprising: about 0.01 to about 5 wt% of at least one stabilizing agent; about 0.001 to about 0.1 wt% of at least one of at least one coloring agent; about 0.1 to about 70 wt% of water; about 0.1 to about 15 wt% of at least one sweetening agent; about 0.1 to about 15 wt% of at least one flavoring agent; about 0.1 to about 4 wt% of at least one cooling agent; about 0.1 to about 5 wt% of at least one surfactant; about 0.1 to about 12 wt% of a triglyceride; about 0.001 to about 5 wt% of a preservative; about 0.1 to about 5 wt% of a polyethylene oxide compound; and about 1 to about 20 wt% of propylene glycol.
25. A method for preparing the consumable film of claim 1, said method comprising: dissolving water-soluble ingredients in water to provide an aqueous solution; mixing at least one water soluble film former and at least one stabilizing agent to provide a film-forming mixture; combining said film-forming mixture and said aqueous solution to provide a hydrated polymer gel; mixing oils to form an oil mixture; adding said oil mixture to said hydrated polymer gel and mixing to provide a uniform gel; casting the uniform gel on a substrate; and drying the cast gel to provide said film.
26. The method of claim 25, wherein said at least one pharmaceutically active agent and said at least one taste masking agent are incoφorated into said aqueous solution or into said uniform gel.
27. The method of claim 25, wherein said at least one taste masking agent is an ion exchange resin, and said at least one pharmaceutically active agent is sorbed to said ion exchange resin without separating ion exchanged pharmaceutically active agent from unexchanged agent and counter ion salts.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU2006201888A AU2006201888B2 (en) | 2000-03-23 | 2006-05-04 | Fast dissolving orally consumable films containing an ion exchange resin as a taste masking agent |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09/535,005 | 2000-03-23 | ||
US09/535,005 US7067116B1 (en) | 2000-03-23 | 2000-03-23 | Fast dissolving orally consumable solid film containing a taste masking agent and pharmaceutically active agent at weight ratio of 1:3 to 3:1 |
PCT/US2001/002192 WO2001070194A1 (en) | 2000-03-23 | 2001-01-23 | Fast dissolving orally consumable films containing an ion exchange resin as a taste masking agent |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AU2006201888A Division AU2006201888B2 (en) | 2000-03-23 | 2006-05-04 | Fast dissolving orally consumable films containing an ion exchange resin as a taste masking agent |
Publications (2)
Publication Number | Publication Date |
---|---|
AU2001229720A1 true AU2001229720A1 (en) | 2001-12-13 |
AU2001229720B2 AU2001229720B2 (en) | 2006-02-02 |
Family
ID=24132458
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AU2972001A Pending AU2972001A (en) | 2000-03-23 | 2001-01-23 | Fast dissolving orally consumable films containing an ion exchange resin as a taste masking agent |
AU2001229720A Ceased AU2001229720B2 (en) | 2000-03-23 | 2001-01-23 | Fast dissolving orally consumable films containing an ion exchange resin as a taste masking agent |
AU2006201888A Ceased AU2006201888B2 (en) | 2000-03-23 | 2006-05-04 | Fast dissolving orally consumable films containing an ion exchange resin as a taste masking agent |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AU2972001A Pending AU2972001A (en) | 2000-03-23 | 2001-01-23 | Fast dissolving orally consumable films containing an ion exchange resin as a taste masking agent |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AU2006201888A Ceased AU2006201888B2 (en) | 2000-03-23 | 2006-05-04 | Fast dissolving orally consumable films containing an ion exchange resin as a taste masking agent |
Country Status (37)
Country | Link |
---|---|
US (2) | US7067116B1 (en) |
EP (2) | EP1267829B1 (en) |
JP (1) | JP4145048B2 (en) |
KR (1) | KR20020084233A (en) |
CN (2) | CN100525835C (en) |
AP (1) | AP2002002648A0 (en) |
AR (1) | AR029494A1 (en) |
AT (1) | ATE324864T1 (en) |
AU (3) | AU2972001A (en) |
BR (1) | BR0109378A (en) |
CA (1) | CA2402988C (en) |
CO (1) | CO5280057A1 (en) |
CR (1) | CR6740A (en) |
CZ (1) | CZ20023108A3 (en) |
DE (1) | DE60119298T2 (en) |
DK (1) | DK1267829T3 (en) |
ES (1) | ES2261455T3 (en) |
GT (1) | GT200100043A (en) |
HK (1) | HK1052880A1 (en) |
HU (1) | HUP0300035A2 (en) |
IL (2) | IL151568A0 (en) |
IS (1) | IS6523A (en) |
MX (1) | MXPA02008425A (en) |
NO (1) | NO20024513D0 (en) |
NZ (1) | NZ520961A (en) |
PA (1) | PA8513901A1 (en) |
PE (1) | PE20011135A1 (en) |
PL (1) | PL357135A1 (en) |
PT (1) | PT1267829E (en) |
RU (1) | RU2256442C2 (en) |
SK (1) | SK13432002A3 (en) |
SV (1) | SV2001000345A (en) |
TW (1) | TWI290474B (en) |
UY (1) | UY26628A1 (en) |
WO (1) | WO2001070194A1 (en) |
YU (1) | YU71502A (en) |
ZA (1) | ZA200206963B (en) |
Families Citing this family (195)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5968547A (en) | 1997-02-24 | 1999-10-19 | Euro-Celtique, S.A. | Method of providing sustained analgesia with buprenorphine |
US6596298B2 (en) * | 1998-09-25 | 2003-07-22 | Warner-Lambert Company | Fast dissolving orally comsumable films |
US20030206942A1 (en) * | 1998-09-25 | 2003-11-06 | Neema Kulkarni | Fast dissolving orally consumable films containing an antitussive and a mucosa coating agent |
US7713566B2 (en) | 1999-12-21 | 2010-05-11 | Zapp Loretta M | Method for enhancing post-processing content of beneficial compounds in beverages |
US6391886B1 (en) * | 2000-12-04 | 2002-05-21 | The Procter & Gamble Company | Oral compositions having improved consumer aesthetics |
US20030003212A1 (en) | 2001-06-13 | 2003-01-02 | Givaudan Sa | Taste modifiers |
US7357891B2 (en) | 2001-10-12 | 2008-04-15 | Monosol Rx, Llc | Process for making an ingestible film |
US20110033542A1 (en) | 2009-08-07 | 2011-02-10 | Monosol Rx, Llc | Sublingual and buccal film compositions |
US8603514B2 (en) * | 2002-04-11 | 2013-12-10 | Monosol Rx, Llc | Uniform films for rapid dissolve dosage form incorporating taste-masking compositions |
US8765167B2 (en) | 2001-10-12 | 2014-07-01 | Monosol Rx, Llc | Uniform films for rapid-dissolve dosage form incorporating anti-tacking compositions |
US8900497B2 (en) | 2001-10-12 | 2014-12-02 | Monosol Rx, Llc | Process for making a film having a substantially uniform distribution of components |
AU2002332118B2 (en) * | 2001-10-12 | 2008-06-26 | Aquestive Therapeutics, Inc. | Glucan based film delivery systems |
US7425292B2 (en) | 2001-10-12 | 2008-09-16 | Monosol Rx, Llc | Thin film with non-self-aggregating uniform heterogeneity and drug delivery systems made therefrom |
JP4879458B2 (en) * | 2001-10-12 | 2012-02-22 | モノソル・アールエックス・エルエルシー | Uniform film for fast dissolving dosage forms containing taste masking composition |
US8663687B2 (en) | 2001-10-12 | 2014-03-04 | Monosol Rx, Llc | Film compositions for delivery of actives |
US20070281003A1 (en) | 2001-10-12 | 2007-12-06 | Fuisz Richard C | Polymer-Based Films and Drug Delivery Systems Made Therefrom |
US11207805B2 (en) | 2001-10-12 | 2021-12-28 | Aquestive Therapeutics, Inc. | Process for manufacturing a resulting pharmaceutical film |
US10285910B2 (en) | 2001-10-12 | 2019-05-14 | Aquestive Therapeutics, Inc. | Sublingual and buccal film compositions |
US20190328679A1 (en) | 2001-10-12 | 2019-10-31 | Aquestive Therapeutics, Inc. | Uniform films for rapid-dissolve dosage form incorporating anti-tacking compositions |
US7666337B2 (en) | 2002-04-11 | 2010-02-23 | Monosol Rx, Llc | Polyethylene oxide-based films and drug delivery systems made therefrom |
US8900498B2 (en) | 2001-10-12 | 2014-12-02 | Monosol Rx, Llc | Process for manufacturing a resulting multi-layer pharmaceutical film |
GB2380936B (en) * | 2001-10-18 | 2003-07-09 | Reckitt Benckiser Healthcare | Improvements in or relating to compositions |
JP2003213038A (en) * | 2001-11-16 | 2003-07-30 | Natl Starch & Chem Investment Holding Corp | Film containing starch |
EP1453909B1 (en) | 2001-12-11 | 2007-10-03 | Ceapro Inc. | Cereal beta glucan compositions, methods of preparation and uses thereof |
DE10207394B4 (en) * | 2002-02-21 | 2007-03-29 | Lts Lohmann Therapie-Systeme Ag | Taste-masked oblate medicinal preparation |
US8017150B2 (en) | 2002-04-11 | 2011-09-13 | Monosol Rx, Llc | Polyethylene oxide-based films and drug delivery systems made therefrom |
WO2003088755A1 (en) * | 2002-04-16 | 2003-10-30 | Vitalstate Canada Ltd. | Delivery systems for functional ingredients |
CA2505796C (en) * | 2002-07-22 | 2012-01-03 | Monosolrx Llc | Packaging and dispensing of rapid dissolve dosage form |
GB0217382D0 (en) * | 2002-07-26 | 2002-09-04 | Pfizer Ltd | Process for making orally consumable dosage forms |
AU2003281744B2 (en) * | 2002-07-29 | 2005-03-10 | Patrick John Shanahan | Oral and dental composition |
AU2002950426A0 (en) * | 2002-07-29 | 2002-09-12 | Patrick John Shanahan | Anti microbial oro-dental system |
US6916463B2 (en) | 2002-09-24 | 2005-07-12 | The Procter & Gamble Company | Oral products having an aesthetic layer |
CA2504610C (en) * | 2002-11-12 | 2012-02-21 | Elan Pharma International Ltd. | Fast-disintegrating solid dosage forms being not friable and comprising pullulan |
US20040131662A1 (en) * | 2003-11-12 | 2004-07-08 | Davidson Robert S. | Method and apparatus for minimizing heat, moisture, and shear damage to medicants and other compositions during incorporation of same with edible films |
US8999372B2 (en) * | 2002-11-14 | 2015-04-07 | Cure Pharmaceutical Corporation | Methods for modulating dissolution, bioavailability, bioequivalence and drug delivery profile of thin film drug delivery systems, controlled-release thin film dosage formats, and methods for their manufacture and use |
US20040191302A1 (en) | 2003-03-28 | 2004-09-30 | Davidson Robert S. | Method and apparatus for minimizing heat, moisture, and shear damage to medicants and other compositions during incorporation of same with edible films |
WO2004045537A2 (en) * | 2002-11-14 | 2004-06-03 | Zengen, Inc. | Edible film for relief of cough or symptoms associated with pharyngitis |
US9561182B2 (en) * | 2003-08-22 | 2017-02-07 | Cure Pharmaceutical Corporation | Edible films for administration of medicaments to animals, methods for their manufacture and methods for their use for the treatment of animals |
CA2533620A1 (en) * | 2002-12-26 | 2004-07-15 | University Of Manitoba | Dissolving film comprising a therapeutically active agent within the film or in a pouch formed by the film |
US20040180110A1 (en) | 2003-03-14 | 2004-09-16 | Atul Mistry | Chewing gum and confectionery compositions containing an endothermic agent |
JP2006515333A (en) * | 2003-03-26 | 2006-05-25 | ザ プロクター アンド ギャンブル カンパニー | Rapidly dissolving edible film composition having improved film strength and stability |
US20040202698A1 (en) * | 2003-04-02 | 2004-10-14 | The Procter & Gamble Company | Drug delivery systems comprising an encapsulated active ingredient |
KR20060003350A (en) * | 2003-04-14 | 2006-01-10 | 에프엠씨 코포레이션 | Homogeneous, thermoreversible alginate films and soft capsules made therefrom |
MXPA05010422A (en) * | 2003-05-02 | 2005-11-04 | Warner Lambert Co | Fast dissolving orally consumable films containing a modified starch for improved heat and moisture resistance. |
BRPI0410956A (en) * | 2003-05-28 | 2006-07-04 | Monosolrx Llc | polyethylene oxide based films and drug delivery systems made from them |
WO2005004989A2 (en) * | 2003-07-01 | 2005-01-20 | Todd Maibach | Film comprising therapeutic agents |
AR045076A1 (en) | 2003-07-24 | 2005-10-12 | Smithkline Beecham Plc | COMPOSITION OF FILM THAT DISSOLVES ORALALLY, MULTICOMPONENT FILM THAT DISSOLVES ORALALLY, USE OF THE FILM COMPOSITION AND THE FILM THAT ORALLY DISSOLVES TO PREPARE A MEDICINAL PRODUCT, FORM OF ORAL DOSAGE AND PROCEDURE FOR PREPARATION OF COMPOSITION |
US8008378B2 (en) * | 2003-07-28 | 2011-08-30 | Novartis Ag | Taste-masked composition of cationic exchange resin |
CA2437639C (en) | 2003-08-11 | 2016-07-05 | Valera Pharmaceuticals, Inc. | Long term drug delivery devices with polyurethane based polymers and their manufacture |
US7858110B2 (en) | 2003-08-11 | 2010-12-28 | Endo Pharmaceuticals Solutions, Inc. | Long term drug delivery devices with polyurethane based polymers and their manufacture |
US20050036977A1 (en) * | 2003-08-11 | 2005-02-17 | Dilip Gole | Taste-masked resinate and preparation thereof |
WO2005032570A1 (en) | 2003-10-06 | 2005-04-14 | Oryza Oil & Fat Chemical Co., Ltd. | Dietetic composition |
US20050075432A1 (en) * | 2003-10-07 | 2005-04-07 | Verrall Andrew P. | Acidulent film and method of making same |
WO2005039499A2 (en) | 2003-10-24 | 2005-05-06 | Adhesives Research, Inc. | Rapidly disintegrating film |
US9248146B2 (en) * | 2003-10-24 | 2016-02-02 | Adhesives Research, Inc. | Dissolvable adhesive films for delivery of pharmaceutical or cosmetic agents |
EP1691631A4 (en) | 2003-11-07 | 2012-09-05 | Us Smokeless Tobacco Co | Tobacco compositions |
US8627828B2 (en) | 2003-11-07 | 2014-01-14 | U.S. Smokeless Tobacco Company Llc | Tobacco compositions |
JP2007511526A (en) * | 2003-11-13 | 2007-05-10 | ディービーシー エルエルシー | Dissolvable thin film xanthone supplement |
AR047658A1 (en) | 2004-02-03 | 2006-02-01 | Cargill Inc | CONCENTRATE OF PROTEINS AND WATER CURRENT WITH HYDROSOLUBBLE CARBOHYDRATES |
US20050186256A1 (en) * | 2004-02-20 | 2005-08-25 | Dihel Deborah L. | Dissolvable film comprising an active ingredient and method of manufacture |
US20060105091A1 (en) * | 2004-11-12 | 2006-05-18 | Sanford L.P. | Non-toxic lava fluids for use in children's products |
JP4898113B2 (en) * | 2004-12-02 | 2012-03-14 | リンテック株式会社 | Oral administration |
WO2006081518A2 (en) * | 2005-01-28 | 2006-08-03 | Collegium Pharmaceutical, Inc. | Non-ionic non-aqueous vehicles for topical and oral administration of carrier-complexed active agents |
US7992575B2 (en) * | 2005-02-28 | 2011-08-09 | U.S. Smokeless Tobacco Company | Use of chlorate, sulfur or ozone to reduce tobacco specific nitrosamines |
JP4955928B2 (en) | 2005-03-01 | 2012-06-20 | 花王株式会社 | Method for producing chlorogenic acid composition |
AU2006242246A1 (en) * | 2005-05-03 | 2006-11-09 | Innozen, Inc. | Edible film for transmucosal delivery of nutritional supplements |
DE102005033943A1 (en) * | 2005-07-20 | 2007-02-22 | Hexal Ag | Non-spitting, oral, fast-disintegrating film for a neuroleptic |
US20070098746A1 (en) * | 2005-11-02 | 2007-05-03 | Nichols William M | Multi-layered coating technology for taste masking |
US7811604B1 (en) | 2005-11-14 | 2010-10-12 | Barr Laboratories, Inc. | Non-effervescent, orally disintegrating solid pharmaceutical dosage forms comprising clozapine and methods of making and using the same |
US20070154542A1 (en) * | 2005-12-30 | 2007-07-05 | Cogentus Pharmaceuticals, Inc. | Oral pharmaceutical formulations containing non-steroidal anti-inflammatory drugs and acid inhibitors |
WO2007089652A2 (en) * | 2006-01-27 | 2007-08-09 | Cadbury Adams Usa Llc | Flavor-enhancing compositions, methods of manufacture, and methods of use |
DE602007010254D1 (en) * | 2006-03-16 | 2010-12-16 | Novartis Ag | SOLID DOSAGE FORM WITH AN ACTIVE AGENT WITH SUPPRESSED TASTE |
RU2435569C2 (en) | 2006-03-16 | 2011-12-10 | Трис Фарма, Инк. | Compositions with modified release, containing complexes medication-ion-exchanging resin |
US20070293581A1 (en) * | 2006-06-05 | 2007-12-20 | Malcolm Hill | Methods for Buccal, Lingual or Sublingual Dosing Regimens of Epinephrine for the Treatment of Allergic Emergencies |
TW200817049A (en) * | 2006-06-05 | 2008-04-16 | Verus Pharmaceuticals Inc | Epinephrine dosing regimens comprising buccal, lingual or sublingual and injectable dosage forms |
WO2008012605A1 (en) * | 2006-07-27 | 2008-01-31 | Techfields Biochem Co. Ltd | Positively charged water-soluble prodrugs of ketoprofen and related compounds with very fast skin penetration rate |
KR101431668B1 (en) * | 2006-08-24 | 2014-08-20 | 맬러드 크리크 폴리머스 아이엔씨. | Cationic latex as a carrier for bioactive ingredients and methods for making and using the same |
WO2008028278A1 (en) * | 2006-09-05 | 2008-03-13 | University Of Manitoba | Antimicrobial coatings |
JP5014712B2 (en) * | 2006-09-06 | 2012-08-29 | ライオン株式会社 | Oral dissolution film |
JP4739452B2 (en) | 2006-09-20 | 2011-08-03 | モノソル アールエックス リミテッド ライアビリティ カンパニー | Eatable water-soluble film containing flavor enhancer to reduce foaming |
HUE038022T4 (en) | 2006-10-02 | 2023-02-28 | Spepharm Ag | Non-mucoadhesive film dosage forms |
EP2120895A2 (en) * | 2007-01-12 | 2009-11-25 | MonoSol Rx LLC | High dose film compositions and methods of preparation |
US20080220029A1 (en) * | 2007-03-05 | 2008-09-11 | Charlene Ng | Fast-dissolving/disintegrating film preparation having high proportion of active |
FR2913597B1 (en) * | 2007-03-14 | 2009-10-09 | Chanel Parfums Beaute Soc Par | COSMETIC USE OF ORGANIC RESINATES |
US8568777B2 (en) * | 2007-03-30 | 2013-10-29 | Monosol Rx, Llc | Packaged film dosage unit containing a complexate |
WO2008137164A1 (en) * | 2007-05-07 | 2008-11-13 | Hwa-Song Liu | Edible thin film strips and process for making |
US8202542B1 (en) | 2007-05-31 | 2012-06-19 | Tris Pharma | Abuse resistant opioid drug-ion exchange resin complexes having hybrid coatings |
US9271524B1 (en) | 2007-09-07 | 2016-03-01 | U.S. Smokeless Tobacco Company | Tobacco having reduced tobacco specific nitrosamine content |
JP2009096803A (en) * | 2007-09-26 | 2009-05-07 | Showa Kako Kk | Oral cavity patch type slowly soluble preparation |
WO2009084017A2 (en) * | 2007-10-10 | 2009-07-09 | Rubicon Research Private Limited | Taste-masked orally disintegrating tablets of memantine hydrochloride |
MY185299A (en) * | 2007-10-11 | 2021-04-30 | Philip Morris Products Sa | Smokeless tobacco product |
US9125434B2 (en) * | 2007-10-11 | 2015-09-08 | Philip Morris Products S.A. | Smokeless tobacco product, smokeless tobacco product in the form of a sheet, extrudable tobacco composition, method for manufacturing a smokeless tobacco product, method for delivering super bioavailable nicotine contained in tobacco to a user, and packaged smokeless tobacco product sheet |
US20090098192A1 (en) * | 2007-10-11 | 2009-04-16 | Fuisz Richard C | Extrudable and Extruded Compositions for Delivery of Bioactive Agents, Method of Making Same and Method of Using Same |
US8354446B2 (en) * | 2007-12-21 | 2013-01-15 | Ligand Pharmaceuticals Incorporated | Selective androgen receptor modulators (SARMs) and uses thereof |
IL188647A0 (en) * | 2008-01-08 | 2008-11-03 | Orina Gribova | Adaptable structured drug and supplements administration system (for oral and/or transdermal applications) |
CA2711932A1 (en) * | 2008-01-31 | 2009-08-13 | Mcneil-Ppc, Inc. | Edible film-strips for immediate release of active ingredients |
WO2009099831A2 (en) * | 2008-01-31 | 2009-08-13 | Mcneil-Ppc, Inc. | Edible film-strips with modified release active ingredients |
FR2933959B1 (en) * | 2008-07-16 | 2010-09-10 | Roquette Freres | PROCESS FOR PRODUCING FILMS DIRECTLY IN ALVEOL |
KR101866189B1 (en) * | 2008-08-25 | 2018-06-11 | 규큐 야쿠힝 고교 가부시키가이샤 | Film preparation containing loperamide hydrochloride |
US9078900B2 (en) * | 2008-09-30 | 2015-07-14 | Braeburn Pharmaceuticals Bvba Sprl | Implantable device for the delivery of risperidone and methods of use thereof |
EP2674150A1 (en) * | 2009-01-28 | 2013-12-18 | Labtec GmbH | Pharmaceutical preparation with improved agent stability |
US20100285130A1 (en) * | 2009-05-06 | 2010-11-11 | Monosol Rx, Llc | Coating of complexed actives in film formulations |
WO2010150930A1 (en) * | 2009-06-25 | 2010-12-29 | (주)벡스코아 | Fast dissolving film for oral administration which prevents unpleasant taste effectively |
KR101074271B1 (en) | 2009-06-25 | 2011-10-17 | (주)차바이오앤디오스텍 | Fast dissolving oral dosage form containing steviosides as a taste masking agent |
JP5663477B2 (en) * | 2009-07-01 | 2015-02-04 | 凸版印刷株式会社 | Acicular body |
NZ597326A (en) | 2009-07-09 | 2013-05-31 | Oshadi Drug Administration Ltd | Matrix carrier compositions, methods and uses |
US8475832B2 (en) | 2009-08-07 | 2013-07-02 | Rb Pharmaceuticals Limited | Sublingual and buccal film compositions |
CN102470101A (en) * | 2009-08-19 | 2012-05-23 | 拜耳医药股份有限公司 | Drug delivery systems (wafer) for pediatric use |
TR200907338A1 (en) * | 2009-09-28 | 2011-04-21 | Yedi̇tepe Üni̇versi̇tesi̇ | A film strip containing natural ingredients. |
US8357398B2 (en) * | 2009-10-21 | 2013-01-22 | Alitair Pharmaceuticals Inc. | Benzonatate compositions and methods of use |
US8701671B2 (en) | 2011-02-04 | 2014-04-22 | Joseph E. Kovarik | Non-surgical method and system for reducing snoring |
US9549842B2 (en) | 2011-02-04 | 2017-01-24 | Joseph E. Kovarik | Buccal bioadhesive strip and method of treating snoring and sleep apnea |
EP2519224A1 (en) * | 2009-12-30 | 2012-11-07 | Novartis AG | Melt extruded thin strips containing coated pharmaceutical actives |
US8397945B2 (en) | 2010-02-23 | 2013-03-19 | R.J. Reynolds Tobacco Company | Dispensing container |
AU2011221889B2 (en) | 2010-03-03 | 2016-04-07 | Kowa Co., Ltd. | Film preparation containing medicament with unpleasant taste |
JP5751868B2 (en) | 2010-03-30 | 2015-07-22 | 日東電工株式会社 | Film-form preparation and method for producing the same |
US20110268809A1 (en) | 2010-04-28 | 2011-11-03 | Paul Andrew Brinkley | Nicotine-Containing Pharmaceutical Compositions |
US20110274628A1 (en) | 2010-05-07 | 2011-11-10 | Borschke August J | Nicotine-containing pharmaceutical compositions |
EP2579844B1 (en) | 2010-06-10 | 2016-02-24 | Midatech Ltd. | Nanoparticle film delivery systems |
US8623409B1 (en) | 2010-10-20 | 2014-01-07 | Tris Pharma Inc. | Clonidine formulation |
US9149959B2 (en) | 2010-10-22 | 2015-10-06 | Monosol Rx, Llc | Manufacturing of small film strips |
JP5555148B2 (en) * | 2010-12-10 | 2014-07-23 | 日東電工株式会社 | Sheet-form preparation and method for producing sheet-form preparation |
US11844720B2 (en) | 2011-02-04 | 2023-12-19 | Seed Health, Inc. | Method and system to reduce the likelihood of dental caries and halitosis |
US10085938B2 (en) | 2011-02-04 | 2018-10-02 | Joseph E. Kovarik | Method and system for preventing sore throat in humans |
US11951139B2 (en) | 2015-11-30 | 2024-04-09 | Seed Health, Inc. | Method and system for reducing the likelihood of osteoporosis |
US11951140B2 (en) | 2011-02-04 | 2024-04-09 | Seed Health, Inc. | Modulation of an individual's gut microbiome to address osteoporosis and bone disease |
US11357722B2 (en) | 2011-02-04 | 2022-06-14 | Seed Health, Inc. | Method and system for preventing sore throat in humans |
US11998479B2 (en) | 2011-02-04 | 2024-06-04 | Seed Health, Inc. | Method and system for addressing adverse effects on the oral microbiome and restoring gingival health caused by sodium lauryl sulphate exposure |
US8287903B2 (en) | 2011-02-15 | 2012-10-16 | Tris Pharma Inc | Orally effective methylphenidate extended release powder and aqueous suspension product |
KR101077468B1 (en) * | 2011-03-04 | 2011-11-07 | (주)차바이오앤디오스텍 | Stable orodispersible film formulation |
CN102138915A (en) * | 2011-03-28 | 2011-08-03 | 于晓勇 | Oral medicine preparation and preparation method thereof |
BR112013031406B1 (en) * | 2011-06-08 | 2022-02-22 | Lts Lohmann Therapie-Systeme Ag | Edible oral film strip and its method of preparation |
US20130078307A1 (en) | 2011-09-22 | 2013-03-28 | Niconovum Usa, Inc. | Nicotine-containing pharmaceutical composition |
US9907748B2 (en) | 2011-10-21 | 2018-03-06 | Niconovum Usa, Inc. | Excipients for nicotine-containing therapeutic compositions |
JP5841433B2 (en) | 2012-01-11 | 2016-01-13 | 日東電工株式会社 | Intraoral film-form base and preparation |
US9763928B2 (en) | 2012-02-10 | 2017-09-19 | Niconovum Usa, Inc. | Multi-layer nicotine-containing pharmaceutical composition |
CN104168895B (en) | 2012-02-28 | 2020-02-21 | 首尔制药株式会社 | Bitter taste-masking high-content fast-dissolving film comprising sildenafil as active ingredient |
US9687445B2 (en) | 2012-04-12 | 2017-06-27 | Lts Lohmann Therapie-Systeme Ag | Oral film containing opiate enteric-release beads |
WO2013171146A1 (en) * | 2012-05-15 | 2013-11-21 | Lts Lohmann Therapie-Systeme Ag | Oral film containing enteric release opiate resinate |
JP6050031B2 (en) * | 2012-06-01 | 2016-12-21 | 森下仁丹株式会社 | Film formulation |
ES2441468B1 (en) | 2012-08-03 | 2014-11-13 | Laboratorios Rubió, S.A. | SOLID PHARMACEUTICAL COMPOSITION OF CATIÓNIC EXCHANGE RESIN. |
BR112015003120B1 (en) | 2012-08-15 | 2022-08-09 | Tris Pharma , Inc | METHYLPHENIDATE EXTENDED RELEASE CHEW TABLET AND ITS USE |
CN102846581A (en) * | 2012-09-28 | 2013-01-02 | 天津市聚星康华医药科技有限公司 | Ambroxol hydrochloride oral fast-dissolving film and preparation method thereof |
CN102836144A (en) * | 2012-09-28 | 2012-12-26 | 天津市聚星康华医药科技有限公司 | Deoxidized epinephrine oral instant film and preparation method thereof |
CN102860997A (en) * | 2012-09-28 | 2013-01-09 | 天津市聚星康华医药科技有限公司 | Ondansetron oral cavity instant membrane capable of sheltering taste and preparation method thereof |
CN102871984B (en) * | 2012-11-05 | 2015-11-11 | 天津市聚星康华医药科技有限公司 | A kind of Phenylephrine hydrochloride oral instant membrane and preparation method thereof |
US11446364B2 (en) | 2012-11-14 | 2022-09-20 | Smith & Nephew, Inc. | Stable thermolysin hydrogel |
CN103860523B (en) * | 2012-12-17 | 2016-09-14 | 天津市聚星康华医药科技有限公司 | Chlorphenamine maleate oral instant membrane and preparation method thereof |
US9668505B2 (en) | 2013-02-18 | 2017-06-06 | Acme Specialty Products, Llc | Taste masking compositions and edible forms thereof for masking the taste of foods |
EP3659630B1 (en) | 2013-03-15 | 2023-12-27 | Smith & Nephew, Inc. | Dissolvable gel-forming film for delivery of active agents |
US10646452B2 (en) | 2013-03-15 | 2020-05-12 | New Jersey Institute Of Technology | System and method for fabrication of uniform polymer films containing nano and micro particles via continuous drying process |
CN103301467A (en) * | 2013-06-20 | 2013-09-18 | 北京阜康仁生物制药科技有限公司 | Stable taste-masking ambroxol hydrochloride compound and preparation method thereof |
WO2015023889A1 (en) * | 2013-08-16 | 2015-02-19 | Luminus Biosciences Inc. | Rapidly-dissolving thin film formulation of water soluble digitalis glycoside for the treatment of congestive heart disease |
KR101407922B1 (en) * | 2013-11-14 | 2014-06-17 | 주식회사 서울제약 | Porous Orally Disintegrating Film comprising pharmacologically active substance and Precess For Producing thereof |
US11980643B2 (en) | 2013-12-20 | 2024-05-14 | Seed Health, Inc. | Method and system to modify an individual's gut-brain axis to provide neurocognitive protection |
US11998574B2 (en) | 2013-12-20 | 2024-06-04 | Seed Health, Inc. | Method and system for modulating an individual's skin microbiome |
US12005085B2 (en) | 2013-12-20 | 2024-06-11 | Seed Health, Inc. | Probiotic method and composition for maintaining a healthy vaginal microbiome |
US11833177B2 (en) | 2013-12-20 | 2023-12-05 | Seed Health, Inc. | Probiotic to enhance an individual's skin microbiome |
US11826388B2 (en) | 2013-12-20 | 2023-11-28 | Seed Health, Inc. | Topical application of Lactobacillus crispatus to ameliorate barrier damage and inflammation |
US11839632B2 (en) | 2013-12-20 | 2023-12-12 | Seed Health, Inc. | Topical application of CRISPR-modified bacteria to treat acne vulgaris |
US11969445B2 (en) | 2013-12-20 | 2024-04-30 | Seed Health, Inc. | Probiotic composition and method for controlling excess weight, obesity, NAFLD and NASH |
EP3613418A1 (en) | 2014-01-17 | 2020-02-26 | Ligand Pharmaceuticals, Inc. | Methods and compositions for modulating hormone levels |
CN106659792B (en) * | 2014-05-08 | 2020-04-28 | 西梯茜生命工学股份有限公司 | Taste-masked oral pharmaceutical formulation containing clomipramine |
US9392814B2 (en) | 2014-06-06 | 2016-07-19 | Nicholas J. Singer | Delivery system for drinks |
US11992508B2 (en) | 2014-10-28 | 2024-05-28 | Biovotec As | Micronized eggshell membrane particles and the use thereof to promote the healing of wounds |
CA2969466A1 (en) * | 2014-12-09 | 2016-06-16 | Monosolrx Llc | Linear polysaccharide based film products |
USD773313S1 (en) | 2015-06-23 | 2016-12-06 | Nicholas J. Singer | Package |
EP3313464B1 (en) | 2015-06-24 | 2020-08-26 | Biovotec AS | Tissue engineering scaffolds comprising particulate egg shell membrane |
US11590228B1 (en) | 2015-09-08 | 2023-02-28 | Tris Pharma, Inc | Extended release amphetamine compositions |
GB201519923D0 (en) | 2015-11-11 | 2015-12-23 | Biovotec Dac And Biovotec As | Dry biocompatible disintegrateable films for delivering particulate egg shell membrane to a wound |
US10532046B2 (en) | 2015-12-03 | 2020-01-14 | Niconovum Usa, Inc. | Multi-phase delivery compositions and products incorporating such compositions |
US20170165252A1 (en) | 2015-12-10 | 2017-06-15 | Niconovum Usa Inc. | Protein-enriched therapeutic composition |
CN105748507B (en) * | 2016-02-26 | 2018-04-17 | 陕西恒远生物科技有限公司 | A kind of gelling agent for alleviating xerostomia |
US11273131B2 (en) | 2016-05-05 | 2022-03-15 | Aquestive Therapeutics, Inc. | Pharmaceutical compositions with enhanced permeation |
CN109310646A (en) | 2016-05-05 | 2019-02-05 | 阿奎斯蒂弗医疗股份有限公司 | Enhance the adrenaline composition of delivering |
CN109996562A (en) | 2016-09-12 | 2019-07-09 | St知识产权控股公司 | The preparation and its preparation and application of 4- methyl -5- (pyrazine -2- base) -3H-1,2- dithiole -3- thioketones |
BR112019004639A2 (en) | 2016-09-12 | 2019-07-16 | St Ip Holding Ag | 4-methyl-5- (pyrazin-2-yl) -3h-1,2-dithiol-3-thione formulations, taste-modified formulations and methods for producing and using them |
CN106475061A (en) * | 2016-11-23 | 2017-03-08 | 郑州莉迪亚医药科技有限公司 | A kind of material for air purification and its preparation method and application |
DE102017112527B4 (en) * | 2017-06-07 | 2019-01-03 | Lts Lohmann Therapie-Systeme Ag | Fast disintegrating foam wafers with a high basis weight |
KR101940401B1 (en) | 2017-06-12 | 2019-01-21 | 경상대학교산학협력단 | Taste masked disintegrating films and preparation method thereof |
WO2019051387A1 (en) | 2017-09-08 | 2019-03-14 | Mingbao Zhang | Methods of using dipivefrin |
US11590081B1 (en) | 2017-09-24 | 2023-02-28 | Tris Pharma, Inc | Extended release amphetamine tablets |
DE102017127434A1 (en) * | 2017-11-21 | 2019-05-23 | Lts Lohmann Therapie-Systeme Ag | Pocket-shaped oral-release films with high drug loading |
CN110314234B (en) * | 2018-03-22 | 2023-12-08 | 广东东阳光药业股份有限公司 | Rosuvastatin calcium resin complex and composition thereof |
WO2019202521A1 (en) * | 2018-04-18 | 2019-10-24 | Shilpa Medicare Limited | Oral disintegrating film compositions of paracetamol |
WO2019204708A1 (en) * | 2018-04-21 | 2019-10-24 | Quest Products, Llc | Bilayer adhering lozenge effective to mask undesirable flavor |
BR112020025604A2 (en) | 2018-06-15 | 2021-03-23 | R.J. Reynolds Tobacco Company | nicotine purification |
CA3108304A1 (en) | 2018-06-21 | 2019-12-26 | Aquestive Therapeutics, Inc. | System and method for making personalized individual unit doses containing pharmaceutical actives |
GB201819978D0 (en) * | 2018-12-11 | 2019-01-23 | Univ Strathclyde | Oral thin films |
EP3930685A1 (en) | 2019-03-01 | 2022-01-05 | Insignis Therapeutics, Inc. | Dipivefrin orally disintegrating tablet formulations |
CN109771396B (en) * | 2019-03-05 | 2022-02-08 | 深圳市新阳唯康科技有限公司 | Oral film containing omeprazole and preparation method thereof |
US11135220B1 (en) | 2020-04-08 | 2021-10-05 | St Ip Holding Ag | Methods of treating viral infections with formulated compositions comprising 4-methyl-5-(pyrazin-2-yl)-3H-1,2-dithiole-3-thione |
US11918689B1 (en) | 2020-07-28 | 2024-03-05 | Tris Pharma Inc | Liquid clonidine extended release composition |
JP2023549381A (en) | 2020-11-18 | 2023-11-24 | バイオファーマ・シナジーズ,エス.エル. | Orodispersible powder compositions containing antihistamine active compounds |
WO2023147443A2 (en) * | 2022-01-26 | 2023-08-03 | Tulex Pharmaceuticals Inc. | Novel compositions |
Family Cites Families (70)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US211136A (en) * | 1879-01-07 | Improvement in chimney-tops | ||
US136922A (en) * | 1873-03-18 | Improvement in extension attachments for stove-pipes | ||
US8008A (en) * | 1851-04-01 | hollingsworth | ||
US206942A (en) * | 1878-08-13 | Improvement in farm-gates | ||
US2990332A (en) | 1958-04-02 | 1961-06-27 | Wallace & Tiernan Inc | Pharmaceutical preparations comprising cation exchange resin adsorption compounds and treatment therewith |
IT629516A (en) | 1959-04-30 | |||
US3117027A (en) | 1960-01-08 | 1964-01-07 | Wisconsin Alumni Res Found | Apparatus for coating particles in a fluidized bed |
US3253944A (en) | 1964-01-13 | 1966-05-31 | Wisconsin Alumni Res Found | Particle coating process |
GB1142325A (en) | 1965-05-14 | 1969-02-05 | Higham Stanley Russell | Means for administering drugs |
US3492131A (en) | 1966-04-18 | 1970-01-27 | Searle & Co | Peptide sweetening agents |
US3784390A (en) | 1971-07-23 | 1974-01-08 | Hayashibara Biochem Lab | Shaped bodies of pullulan and their use |
US4136145A (en) | 1974-07-05 | 1979-01-23 | Schering Aktiengesellschaft | Medicament carriers in the form of film having active substance incorporated therein |
US4197289A (en) | 1975-12-15 | 1980-04-08 | Hoffmann-La Roche Inc. | Novel dosage forms |
US4221778A (en) | 1979-01-08 | 1980-09-09 | Pennwalt Corporation | Prolonged release pharmaceutical preparations |
AU5957480A (en) | 1979-07-26 | 1981-01-29 | American Cyanamid Company | Diethyl carbamazine resinate |
US4562020A (en) | 1982-12-11 | 1985-12-31 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | Process for producing self-supporting glucan film |
US4581232A (en) | 1983-07-20 | 1986-04-08 | Warner-Lambert Company | Magnesium trisilicate suitable for preparation of medicament adsorbates |
US4650663A (en) | 1983-07-20 | 1987-03-17 | Warner-Lambert Company | Magnesium trisilicate suitable for preparation of medicament adsorbates of antitussives |
US4762709A (en) | 1983-09-16 | 1988-08-09 | Pennwalt Corporation | Liquid prolonged release pharmaceutical formulations containing ionic constituents |
JPS60219238A (en) | 1984-04-14 | 1985-11-01 | Hayashibara Biochem Lab Inc | Formed product containing slowly disintegrating pullulan and its production |
US4788055A (en) | 1985-12-09 | 1988-11-29 | Ciba-Geigy Corporation | Resinate sustained release dextromethorphan composition |
IL78826A (en) | 1986-05-19 | 1991-05-12 | Yissum Res Dev Co | Precursor composition for the preparation of a biodegradable implant for the sustained release of an active material and such implants prepared therefrom |
US4713243A (en) * | 1986-06-16 | 1987-12-15 | Johnson & Johnson Products, Inc. | Bioadhesive extruded film for intra-oral drug delivery and process |
CA1313620C (en) | 1986-08-08 | 1993-02-16 | Yasunobu Okada | Oral drug delivery systems |
EP0256611A1 (en) | 1986-08-08 | 1988-02-24 | Squibb Japan Inc. | Oral drug delivery systems |
JPS6359855A (en) | 1986-08-29 | 1988-03-15 | Jun Kawai | Edible film |
DE3630603A1 (en) | 1986-09-09 | 1988-03-10 | Desitin Arzneimittel Gmbh | PHARMACEUTICAL AND DOSAGE FORM FOR MEDICINAL ACTIVE SUBSTANCES, REAGENTS OR THE LIKE, AND METHOD FOR THE PRODUCTION THEREOF |
JPH0739508B2 (en) | 1986-11-11 | 1995-05-01 | 株式会社林原生物化学研究所 | Pullulan / polyethylene glycol aggregate, its production method and use |
JPS63250319A (en) | 1987-04-06 | 1988-10-18 | Fujimoto Seiyaku Kk | Pharmaceutical preparation suitable in oral cavity |
JPS63250318A (en) | 1987-04-06 | 1988-10-18 | Fujimoto Seiyaku Kk | Pharmaceutical preparation suitable in oral cavity |
US4820506A (en) | 1987-05-01 | 1989-04-11 | Research Foundation, State University Of New York | Salivary stimulant |
JPS63280014A (en) | 1987-05-12 | 1988-11-17 | Sekisui Chem Co Ltd | Plaster composition for bad breath prevention |
JPS63296655A (en) | 1987-05-29 | 1988-12-02 | Toppan Printing Co Ltd | Production of edible sheet |
JP2642354B2 (en) | 1987-06-11 | 1997-08-20 | 株式会社 三和化学研究所 | Manufacturing method of sustained release buccal |
JPS63310818A (en) | 1987-06-12 | 1988-12-19 | Sato Seiyaku Kk | Sheet preparation to be applied to oral mucosa |
IL90245A (en) * | 1988-05-11 | 1994-04-12 | Glaxo Group Ltd | Resin adsorbate comprising ranitidine together with a synthetic cation exchange resin, its preparation and pharmaceutical compositions containing it |
US5047244A (en) | 1988-06-03 | 1991-09-10 | Watson Laboratories, Inc. | Mucoadhesive carrier for delivery of therapeutical agent |
DE3827561C1 (en) | 1988-08-13 | 1989-12-28 | Lts Lohmann Therapie-Systeme Gmbh & Co Kg, 5450 Neuwied, De | |
US4996047A (en) | 1988-11-02 | 1991-02-26 | Richardson-Vicks, Inc. | Sustained release drug-resin complexes |
JPH0645536B2 (en) * | 1989-01-31 | 1994-06-15 | 日東電工株式会社 | Oral mucosa patch and oral mucosa patch preparation |
US5354551A (en) | 1989-10-14 | 1994-10-11 | Desitin Arzneimittel Gmbh | Oral and dental hygiene preparation |
US5188825A (en) * | 1989-12-28 | 1993-02-23 | Iles Martin C | Freeze-dried dosage forms and methods for preparing the same |
IT1238072B (en) | 1990-01-19 | 1993-07-03 | Sclavo Spa | PHARMACEUTICAL COMPOSITIONS AND DOSAGE FORMS FOR ORAL ADMINISTRATION OF CALCITONIN |
DE4018247A1 (en) | 1990-06-07 | 1991-12-12 | Lohmann Therapie Syst Lts | MANUFACTURING METHOD FOR QUICK-DISINFITTING FILM-SHAPED PHARMACEUTICAL FORMS |
JPH051198A (en) | 1991-06-26 | 1993-01-08 | Japan Happy:Kk | Water-soluble film |
JPH05236885A (en) | 1991-07-17 | 1993-09-17 | Tazawa Toshihiko | Flavoring and refreshing food formed into film |
JPH0541602A (en) | 1991-08-06 | 1993-02-19 | Fujitsu General Ltd | Primary radiator in common use with circularly polarized wave and linearly polarized wave |
JP3232488B2 (en) | 1992-08-20 | 2001-11-26 | 株式会社林原生物化学研究所 | High content of pullulan, its production method and use |
US5411945A (en) | 1992-08-29 | 1995-05-02 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | Pullulan binder and its uses |
JPH09504810A (en) | 1993-08-19 | 1997-05-13 | シグナス,インコーポレイテッド | Water-soluble pressure sensitive mucoadhesive |
GB9409466D0 (en) * | 1994-05-12 | 1994-06-29 | Ciba Geigy Ag | Textile treatment |
US5529783A (en) | 1994-12-19 | 1996-06-25 | Mcneil-Ppc, Inc. | Rotor granulation and coating of acetaminophen, pseudoephedrine, chlorpheniramine, and, optionally dextromethorphan |
WO1996039126A2 (en) * | 1995-06-06 | 1996-12-12 | Warner-Lambert Company | Ranitidine salts on magnesium trisilicate as an adsorbate |
JPH09124512A (en) | 1995-10-26 | 1997-05-13 | Res Inst For Prod Dev | Water-soluble medicine-pullulan combination preparation for targeting liver |
JP2791317B2 (en) * | 1995-12-26 | 1998-08-27 | 株式会社三和化学研究所 | Multilayer film preparation |
AU4428397A (en) | 1996-09-20 | 1998-04-14 | Warner-Lambert Company | Oral compositions containing a zinc compound |
US5800832A (en) * | 1996-10-18 | 1998-09-01 | Virotex Corporation | Bioerodable film for delivery of pharmaceutical compounds to mucosal surfaces |
DE19646392A1 (en) | 1996-11-11 | 1998-05-14 | Lohmann Therapie Syst Lts | Preparation for use in the oral cavity with a layer containing pressure-sensitive adhesive, pharmaceuticals or cosmetics for dosed delivery |
DE19652268C2 (en) | 1996-12-16 | 2000-06-29 | Lohmann Therapie Syst Lts | Medicinal preparation for the release of apomorphine in the oral cavity |
DE19652188C2 (en) | 1996-12-16 | 2002-02-14 | Lohmann Therapie Syst Lts | Flat drug preparation for application and release of buprenorphine or a pharmacologically comparable substance in the oral cavity and process for its preparation |
WO1998027961A2 (en) | 1996-12-20 | 1998-07-02 | Warner Lambert Company | Antitussive drugs delivered by partially coated ion exchange resins |
JPH10179045A (en) | 1996-12-25 | 1998-07-07 | Osaka Kagaku Gokin Kk | Sheet-like edible molding |
US5980882A (en) | 1997-04-16 | 1999-11-09 | Medeva Pharmaceuticals Manufacturing | Drug-resin complexes stabilized by chelating agents |
US6136297A (en) | 1997-06-06 | 2000-10-24 | The Procter & Gamble Company | Delivery system for an oral care substance using a strip of material having low flexural stiffness |
JP3460538B2 (en) | 1997-10-08 | 2003-10-27 | 救急薬品工業株式会社 | Fast dissolving film preparation |
EP1079813B1 (en) * | 1998-04-29 | 2005-02-09 | Virotex Corporation | Pharmaceutical carrier device suitable for delivery of pharmaceutical compounds to mucosal surfaces |
US20030206942A1 (en) | 1998-09-25 | 2003-11-06 | Neema Kulkarni | Fast dissolving orally consumable films containing an antitussive and a mucosa coating agent |
US6596298B2 (en) | 1998-09-25 | 2003-07-22 | Warner-Lambert Company | Fast dissolving orally comsumable films |
US20030211136A1 (en) | 1998-09-25 | 2003-11-13 | Neema Kulkarni | Fast dissolving orally consumable films containing a sweetener |
US6552024B1 (en) * | 1999-01-21 | 2003-04-22 | Lavipharm Laboratories Inc. | Compositions and methods for mucosal delivery |
-
2000
- 2000-03-23 US US09/535,005 patent/US7067116B1/en not_active Expired - Fee Related
-
2001
- 2001-01-23 CN CNB2004101003959A patent/CN100525835C/en not_active Expired - Fee Related
- 2001-01-23 MX MXPA02008425A patent/MXPA02008425A/en active IP Right Grant
- 2001-01-23 JP JP2001568392A patent/JP4145048B2/en not_active Expired - Fee Related
- 2001-01-23 CA CA002402988A patent/CA2402988C/en not_active Expired - Fee Related
- 2001-01-23 AP APAP/P/2002/002648A patent/AP2002002648A0/en unknown
- 2001-01-23 CN CNB018069983A patent/CN1181814C/en not_active Expired - Fee Related
- 2001-01-23 PL PL01357135A patent/PL357135A1/en not_active Application Discontinuation
- 2001-01-23 NZ NZ520961A patent/NZ520961A/en not_active IP Right Cessation
- 2001-01-23 ES ES01959912T patent/ES2261455T3/en not_active Expired - Lifetime
- 2001-01-23 KR KR1020027012429A patent/KR20020084233A/en not_active Application Discontinuation
- 2001-01-23 AT AT01959912T patent/ATE324864T1/en not_active IP Right Cessation
- 2001-01-23 EP EP01959912A patent/EP1267829B1/en not_active Revoked
- 2001-01-23 BR BR0109378-9A patent/BR0109378A/en not_active Application Discontinuation
- 2001-01-23 DK DK01959912T patent/DK1267829T3/en active
- 2001-01-23 WO PCT/US2001/002192 patent/WO2001070194A1/en active Application Filing
- 2001-01-23 HU HU0300035A patent/HUP0300035A2/en unknown
- 2001-01-23 AU AU2972001A patent/AU2972001A/en active Pending
- 2001-01-23 IL IL15156801A patent/IL151568A0/en active IP Right Grant
- 2001-01-23 YU YU71502A patent/YU71502A/en unknown
- 2001-01-23 PT PT01959912T patent/PT1267829E/en unknown
- 2001-01-23 DE DE60119298T patent/DE60119298T2/en not_active Expired - Lifetime
- 2001-01-23 RU RU2002128354/15A patent/RU2256442C2/en not_active IP Right Cessation
- 2001-01-23 CZ CZ20023108A patent/CZ20023108A3/en unknown
- 2001-01-23 AU AU2001229720A patent/AU2001229720B2/en not_active Ceased
- 2001-01-23 EP EP06007766A patent/EP1674078A3/en not_active Withdrawn
- 2001-01-23 SK SK1343-2002A patent/SK13432002A3/en unknown
- 2001-02-07 TW TW090102651A patent/TWI290474B/en not_active IP Right Cessation
- 2001-03-15 SV SV2001000345A patent/SV2001000345A/en not_active Application Discontinuation
- 2001-03-21 GT GT200100043A patent/GT200100043A/en unknown
- 2001-03-21 PE PE2001000261A patent/PE20011135A1/en not_active Application Discontinuation
- 2001-03-21 CO CO01022573A patent/CO5280057A1/en active IP Right Grant
- 2001-03-21 UY UY26628A patent/UY26628A1/en not_active Application Discontinuation
- 2001-03-21 PA PA20018513901A patent/PA8513901A1/en unknown
- 2001-03-22 AR ARP010101341A patent/AR029494A1/en unknown
-
2002
- 2002-08-23 IS IS6523A patent/IS6523A/en unknown
- 2002-08-27 CR CR6740A patent/CR6740A/en not_active Application Discontinuation
- 2002-08-29 ZA ZA200206963A patent/ZA200206963B/en unknown
- 2002-09-20 NO NO20024513A patent/NO20024513D0/en not_active Application Discontinuation
-
2003
- 2003-07-17 HK HK03105167.3A patent/HK1052880A1/en unknown
-
2006
- 2006-05-04 AU AU2006201888A patent/AU2006201888B2/en not_active Ceased
- 2006-05-05 US US11/429,547 patent/US7648712B2/en not_active Expired - Fee Related
-
2011
- 2011-02-28 IL IL211482A patent/IL211482A0/en unknown
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US7648712B2 (en) | Fast dissolving orally consumable films containing a taste masking agent | |
AU2001229720A1 (en) | Fast dissolving orally consumable films containing an ion exchange resin as a taste masking agent | |
US20150359739A1 (en) | Edible film-strips for immediate release of active ingredients | |
US20090196908A1 (en) | Edible film-strips with modified release active ingredients | |
US7407669B2 (en) | Fast dissolving orally consumable films | |
CA2317021A1 (en) | Tablet composition | |
CA2572461C (en) | Physiological compatible film |