WO2002007711A1 - Compositions and films for capsule manufacture - Google Patents
Compositions and films for capsule manufacture Download PDFInfo
- Publication number
- WO2002007711A1 WO2002007711A1 PCT/US2001/012459 US0112459W WO0207711A1 WO 2002007711 A1 WO2002007711 A1 WO 2002007711A1 US 0112459 W US0112459 W US 0112459W WO 0207711 A1 WO0207711 A1 WO 0207711A1
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- WO
- WIPO (PCT)
- Prior art keywords
- weight
- film
- poly
- water
- polymer component
- Prior art date
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4816—Wall or shell material
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
Definitions
- the present invention relates to alkylene oxide polymer containing compositions which can be formed into flexible films having properties suitable for replacement of gelatin containing films in the manufacture of soft or hard shell capsules.
- the present invention further relates to processes for forming such alkylene oxide containing polymer films and the use of such films in the manufacture of soft shell capsules on conventional encapsulation equipment such as a rotary die machine.
- gelatin containing compositions are commonly used in the manufacture of capsules, particularly soft capsules for the delivery of a variety of liquid or solid ingredients in pharmaceutical, agricultural and other applications. Such films are generally strong and tough and have processing properties which make them suitable for use in the manufacture of capsules.
- gelatin is a protein material produced by hydrolysis of collagen from animal bones and connective tissues. Since gelatin is derived from animal sources, there are often inconsistencies in product quality from batch to batch. The physical and chemical properties of gelatin are a function of the source of the collagen, the method of rendering and refining the crude feed stock, and the chemical nature of impurities and additives which may be present.
- WO 99/40156 discloses manufacturing capsules from compositions containing a mixture of different molecular weight poly(alkylene oxide) polymers in which water is used to compatibilize the mixture of polymers. None of these prior art efforts have resulted in films having all of the physical and mechanical properties required to successfully replace gelatin films in the commercial manufacture of capsules. Summary of the Invention
- thin flexible films made from compositions containing poly(alkylene oxide) polymers which can replace gelatin films in the manufacture of capsules.
- the poly(alkylene oxide) polymer containing films of the present invention are prepared by blending a poly(alkylene oxide) polymer component with an appropriate amount of water and optionally a plasticizer and/or other ingredients and extruding or otherwise forming a thin flexible film which is particularly suitable for the formation of capsule shells.
- compositions of the present invention typically yield a film with mechanical properties in desired ranges, e.g., having a stress of less than 250 psi at a strain of 100% as determined by a mechanical tensile test in accordance with ASTM D882-97 and an Indentation Index of less than 8 as determined by the HH Indentation Test described hereinafter.
- the poly(alkylene oxide) polymer containing films of the present invention can be used in known processes and apparatus for the manufacture of capsules for pharmaceutical, agricultural and other applications.
- compositions of the present invention suitable for forming films useful in the manufacture of capsules comprise;
- compositions may be formed into the films of the present invention by known means such as extrusion.
- the thin, easily extensible, films of the present invention which are suitable for the preparation of capsules comprise;
- the poly(alkylene oxide) polymers used to obtain the films of the present invention are prepared from alkylene oxide monomers containing from about 2 to 5 carbon atoms per molecule, e.g., ethylene oxide or propylene oxide, as well as copolymers and derivatives thereof. Polymers of a desired molecular weight may be obtained directly from the polymerization of the alkylene oxide monomers or by blending poly(alkylene oxide) polymers of different molecular weights.
- the term "molecular weight” means number average molecular weight. Methods for determining number average molecular weight such as gel permeation chromatography, light scattering techniques and rheological measuring techniques are known to those skilled in the art. The molecular weights used in this specification were determined by rheological measurements. These alkylene oxide polymers useful in the present invention are water soluble and have a molecular weight of from about 100,000 to 8,000,000 g/mol.
- the poly(alkylene oxide) polymers used to obtain the films of the present invention comprise ethylene oxide polymers.
- the ethylene oxide polymers include, for example, homopolymers of ethylene oxide and copolymers of ethylene oxide with one or more polymerizable comonomers.
- the particular comonomer is not critical to the present invention and may contain hydrocarbon substituents, such as, for example, alkyl, cycloalkyl, aromatic, alkene (also referred to as alkylene) or branched alkyl or alkene groups; provided, however, that the water solubility or water-dispersibility is maintained.
- Methods of preparing ethylene oxide polymers useful in the present invention are well known in the art. See for example, U.S.
- Poly(alkylene oxide) polymers useful in the present are commercially available, for example, from Union Carbide Corporation, a subsidiary of Dow Chemical Company, under the tradename POLYOX ® Water Soluble Resins. These homopolymers of ethylene oxide have a molecular weight of from about 100,000 to 8,000,000 g/mol.
- a single molecular weight grade of poly(alkylene oxide) polymer or a blend of two or more grades of such polymers in appropriate proportions can be used.
- the molecular weight of the poly(alkylene oxide) chosen for use in preparing a film of the present invention will largely be determined by the type of capsule to be manufactured and its intended use. In general, the molecular weight of the polymer is chosen on the basis of the time required for the capsules made therefrom to dissolve in the fluid environment present in the intended use.
- the poly(alkylene oxide) polymer component will normally have a molecular weight in the range of 200,000 to 400,000 g/mol., whereas higher molecular weight polymers are suitable for slower dissolving capsules.
- the poly(alkylene oxide) containing polymer component of the compositions from which the films of the present invention are formed may comprise additional polymers in order to achieve desired properties.
- Such other polymers include, for example, naturally occurring and synthetic neutral, cationic, and anionic polymers, e.g., polysaccharides and derivatives thereof, hyaluronic acid, other cross- linked polyalkylene oxides, polyvinyl pyrrolidones, polycaprolactones, polyvinyl acetates and polycarboxylic acids, polyacrylic acid and polyvinyl acetate.
- the polysaccharides include naturally occurring, biosynthesized and derivatized carbohydrate polymers and mixtures thereof.
- Such materials encompass high molecular weight polymers composed of monosaccharide units joined by glycosidic bonds.
- These materials may include, for example, the entire starch and cellulose families; pectin; chitosan; chitin; the seaweed products such as agar and carrageenan; alginate; the natural gums such as guar, arabic and tragacanth; bio-derived gums such as xanthan; and the like.
- Common polysaccharides include cellulosics conventionally employed for the preparation of cellulose ethers, such as, for example, chemical cotton, cotton linters, wood pulp, alkali cellulose and the like. Such materials are commercially available. The molecular weight of the polysaccharides typically ranges from about 10,000 to 2,000,000 grams per mole.
- the polysaccharides are etherified by reacting the polysaccharide with an alkylene oxide, e.g., ethylene oxide, propylene oxide or butylene oxide or otherwise derivatized by techniques known to those skilled in the art.
- an alkylene oxide e.g., ethylene oxide, propylene oxide or butylene oxide or otherwise derivatized by techniques known to those skilled in the art.
- polymers When such other polymers are used in the film forming compositions of the present invention, they are typically present in amounts of less than about 70% by weight, and more typically from about 10 to 40% by weight, based on the total weight of the polymer component. Particularly good results have been obtained when the polymer component contains at least about 50% by weight poly (ethylene oxide).
- the weight percentages of the various components of the film forming compositions of the present invention are based on the total weight of the composition, including the polymer component, water, plasticizers and other components as hereinafter described.
- the poly(alkylene oxide) polymer containing compositions used to form the films of the present invention contain water in an amount of from about 14 to about 50% by weight, more preferably from about 20 to about 35% by weight, based on the total weight of the film forming composition.
- higher molecular weight poly(alkylene oxide) polymers require larger amounts of water to achieve the same flexibility compared to low molecular weight poly(alkylene oxide) polymers.
- the water should present in an amount sufficient to be effective as an internal plasticizer when the compositions are used to form the films of the present invention, e.g. by extrusion. Care must be taken to maintain the water content of the finished films of the present invention above about 14 % by weight when used in the manufacture of capsules to obtain the physical and mechanical properties necessary to make them suitable to replace gelatin based films.
- plasticizers may also advantageously be included in the compositions from which the films of the present invention are formed. Such plasticizers modify the films' properties making them softer and more ductile and also help maintain the water content in the films, which is believed to enhance the flexibility and sealability of the films during the encapsulation step.
- plasticizers which are particularly useful as plasticizers in the present invention are capable of forming hydrogen bonds with poly(alkylene oxide).
- plasticizer compounds examples include pol hydric alcohols such as glycerin, propylene glycol, sorbitol and the like, carboxylic acids and their derivatives including adipic acid, triethyl citrate and the like, and sugars such as glucose, fructose, xylose and the like. All of the plasticizers may be used alone or in mixture thereof. Plasticizer compounds may be present in the film forming compositions of the present invention in an amount of from 1 to about 40% by weight, preferably from about 5 to about 30 % by weight.
- Such other components include, for example, stabilizers, preservatives, antioxidants, colorants, flavorants, opacifing agents, processing aids, fillers and the like.
- stabilizers for example, stabilizers, preservatives, antioxidants, colorants, flavorants, opacifing agents, processing aids, fillers and the like.
- the films of the present invention may be prepared with conventional apparatus by conventional film forming processes, preferably extrusion.
- the polymer component containing the poly(alkylene oxide) having the selected molecular weight is first uniformly blended with water and optionally a plasticizer and any other components in a conventional mixer such as a Henchel mixer, V blender or Hobart mixer.
- a conventional mixer such as a Henchel mixer, V blender or Hobart mixer.
- the various components are added separately to an extruder with solid components being added by way of a metered feeder and liquid components being added by way of a metered pump, and formed into a homogeneous mixture inside the extruder.
- the water content of the blended composition should be sufficient to avoid excessive extrusion torque but not so great as to produce films which lack sufficient tensile strength to maintain their shape.
- Caution should be taken to avoid excess loss of water during film production and transportation.
- the extruder and die temperatures are kept below the boiling point of water to prevent excess water evaporation.
- the techniques and conditions to be employed in extruding the films of the present invention will be readily apparent to the skilled artesian and are described, for example, in U.S. Patent 3,941,865 which is incorporated herein by reference.
- the films of the present invention are easily extensible and for most applications will have a thickness of from about 5 to about 50 mils.
- the films of the present invention are preferably self sealing, that is, the films should be able to seal onto themselves with the help of elevated temperature, pressure, or both, and without the necessity of being solvated.
- a preferred use for the poly(alkylene oxide) containing films of the present invention is in the manufacture of soft capsules.
- the films of the present invention can replace gelatin based films in the manufacture of soft shell capsules.
- the soft shell capsules can be prepared by a rotary die process in which they are formed, filled, and sealed in a single operation. An example of such a process is described in PCT International Publication No. WO 97/35537. Since the poly(alkylene oxide) containing films of the present invention expel water quickly even at room temperature, capsules prepared from such films may be dried rapidly thus saving energy and reducing production times.
- Capsule shells made from the films of the present invention have a very low water content, typically from 0 to about 5%, depending on film composition and resist moisture uptake even in relatively humid conditions while providing excellent mechanical strength.
- the films of the present invention are ideal for encapsulating moisture sensitive materials and meet other standard requirements for capsules including maintenance of capsule shape under external pressure, good solubilit in gastro-intestinal fluid and stability for long term storage.
- the films of the present invention may be used to encapsulate a wide range of substances in the form of solids or liquids.
- capsules prepared from the films of the present invention will have a variety of industrial and personal care uses.
- the capsules can be used for the oral delivery of pharmaceutically active agents to humans and animals.
- the liquid filing material comprises a physiologically acceptable carrier such as those used in gelatin capsules including, for example, poly(ethylene glycol), vegetable oil, lecithin, mineral oil, etc.
- the capsules can be used in personal care applications, e.g., hair care and skin care formulations, to deliver oils, vitamins, proteins, polymers and other personal care ingredients.
- the capsules can also be used, for example, to provide bath oil beads, fragrances and time released ingredients. Further, the capsules can be used in the manufacture of paint balls and other recreational products. Moreover, the capsules can be employed in a variety of industrial uses, such as, for example, in the delivery of inks, catalysts, initiators, enzymes, and the like. The size and shape of the capsules and details concerning the selection and amounts of the appropriate filling materials and active ingredients can be determined by those skilled in the art and are not a critical part of the present invention.
- the processability of the film to form soft shell capsules can be determined by the tensile test and by the "HH Indentation Test".
- stress is a measure, in pounds per square inch (psi), of the force per unit area required to achieve a certain strain and is determined in accordance with the procedures of ASTM D882-97.
- Stress is determined by subtracting the length of a piece of film to be tested at rest from the length of the piece of film after it has been stretched and dividing that number by the length of the piece of film at rest.
- HH Indentation Test measures the ability of a film to be deformed into a half capsule shape. The test is performed using a TA- XT2 Texture Analyzer (Stable Micro Systems, Haslemere, UK). A piece of film to be tested is placed between two plates which are bolted together. Each plate has a hole in its center exposing a circular section of the film sample approximately 0.6 inches in diameter. A probe comprising a cylindrical rod having a diameter of 0.5 inches and a rounded tip having a radius of 6.4mm is positioned to push against the exposed section of film.
- the Indentation Index represents the amount of force, in pounds, required to move the probe a certain distance when the probe is moving at a certain speed.
- the distance the probe travels represents the depth of the indentation the probe makes in the film.
- the Indentation Index is determined using a film sample formed to a thickness of 25 mils with the probe moving at a speed of 1 mm/second and traveling a distance of 6.4 mm.
- a film sample that is suitable to use on a typical soft-shell capsule encapsulation machine must have an Indentation Index value of less than 8.
- the freshly extruded film was placed in an incubator with circulating air under controlled condition of 50% relative humidity at 25 °C. Samples were taken at different time intervals to determine the water content in the films. The results, which are shown in Table 1, indicate that the poly(ethylene oxide) based films lose water readily.
- a mixture of POLYOX WSR N-750, glycerin and water was extruded on a Brabender ® Conical Twin Screw Extruder (Model CTSE- V) operated at low temperatures (feed 25-45 °C, barrel 50-90 °C, die 80-110 °C).
- the extruded film was collected in the same manner as described in Example 1.
- the screw speed was 20 to 50 rpm, and the torque was -2000 mg.
- the solid POLYOX WSR N-750 powder was meter-fed into the extruder with a K-Tron Volumetric Feeder Model K2MV-720, and the liquid containing water and glycerin was metered into the extruder with a MasterFlex Peristaltic Pump Model PM- 77914. Both the solid and liquid addition rates were controlled, so that the composition contains POLYOX WSR N-750/glycerin in a ratio of 4:1, and the water content in the finished extruded film was about 30 wt% .
- Indentation tests were also performed to evaluate the processability of the extruded film in making soft shell capsule. This test was performed on a TA-XT2 Texture Analyzer (Stable Micro Systems, Haslemere, UK) in accordance with procedures described previously herein to measure the extension and elasticity of the film.
- EXAMPLE 5 Poly(ethylene oxide) having a molecular weight of 200,000 g/gmol (POLYOX WSR N-80) and glycerin in a weight to weight ratio of 5:1 were first mixed for 2 minutes with a mortar and pestle. Water was then added slowly to the mixture in an amount sufficient to provide a total of 20 wt.% and the mixing was continued for an additional 10 minutes. The doughy mixture (-20 g) was transferred to a Brabender head mixer (D-51, No 507) operated at 80 °C and 10 RPM. After mixing for 5 minutes, an aliquot of hot mixture was taken out, placed between two aluminum plates and pressed on a hydraulic press at 2000 PSI and 90 °C. After pressing for 2 minutes, the film was released from the mold and sealed in a plastic bag. The mechanical properties of the compressed film are presented in Table 9. Table 9
- Ellipsoidal shaped capsules were prepared from films of the previous examples on a small mold that simulates the action of an encapsulation rotary die. The film was heated gently just prior to sealing when water content was below 20% and required no heating when water content was about 30%. The resulting capsules had strong seals. The finished (dry) capsules appeared opaque and had a smooth surface and a strong seam. They retained their shapes well under external force. The capsules were filled with vegetable oil or poly(ethylene glycol). These capsules ruptured within 30 minutes in a dissolution test defined by U.S. Pharmacopeia, 24 rev.;.U.S. Pharmacopeial Convention: Rockville, MD, 2000; pp. 1941-1942 by stirring (50 rpm) at 37 °C in 0.1 N HC1 (1000 mL). In general, the capsules dissolve faster with higher plasticizer contents and thinner shells. Results of the disintegration test are presented in Table 11.
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Abstract
Description
Claims
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU2001255429A AU2001255429A1 (en) | 2000-07-21 | 2001-04-17 | Compositions and films for capsule manufacture |
JP2002513447A JP2004504445A (en) | 2000-07-21 | 2001-04-17 | Composition and film for capsule production |
MXPA03000624A MXPA03000624A (en) | 2000-07-21 | 2001-04-17 | Compositions and films for capsule manufacture. |
CA002416257A CA2416257A1 (en) | 2000-07-21 | 2001-04-17 | Compositions and films for capsule manufacture |
KR10-2003-7000858A KR20030023709A (en) | 2000-07-21 | 2001-04-17 | Compositions and films for capsule manufacture |
EP01928586A EP1305011A1 (en) | 2000-07-21 | 2001-04-17 | Compositions and films for capsule manufacture |
BR0112599-0A BR0112599A (en) | 2000-07-21 | 2001-04-17 | Capsule Manufacturing Compositions and Films |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US22005200P | 2000-07-21 | 2000-07-21 | |
US60/220,052 | 2000-07-21 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2002007711A1 true WO2002007711A1 (en) | 2002-01-31 |
Family
ID=22821853
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2001/012459 WO2002007711A1 (en) | 2000-07-21 | 2001-04-17 | Compositions and films for capsule manufacture |
Country Status (8)
Country | Link |
---|---|
EP (1) | EP1305011A1 (en) |
JP (1) | JP2004504445A (en) |
KR (1) | KR20030023709A (en) |
AU (1) | AU2001255429A1 (en) |
BR (1) | BR0112599A (en) |
CA (1) | CA2416257A1 (en) |
MX (1) | MXPA03000624A (en) |
WO (1) | WO2002007711A1 (en) |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8652378B1 (en) | 2001-10-12 | 2014-02-18 | 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 |
US8900498B2 (en) | 2001-10-12 | 2014-12-02 | Monosol Rx, Llc | Process for manufacturing a resulting multi-layer pharmaceutical film |
US8906277B2 (en) | 2001-10-12 | 2014-12-09 | Monosol Rx, Llc | Process for manufacturing a resulting pharmaceutical film |
US9108340B2 (en) | 2001-10-12 | 2015-08-18 | Monosol Rx, Llc | Process for manufacturing a resulting multi-layer pharmaceutical film |
US10272607B2 (en) | 2010-10-22 | 2019-04-30 | Aquestive Therapeutics, Inc. | Manufacturing of small film strips |
US10285910B2 (en) | 2001-10-12 | 2019-05-14 | Aquestive Therapeutics, Inc. | Sublingual and buccal film compositions |
US10821074B2 (en) | 2009-08-07 | 2020-11-03 | Aquestive Therapeutics, Inc. | Sublingual and buccal film compositions |
US11077068B2 (en) | 2001-10-12 | 2021-08-03 | Aquestive Therapeutics, Inc. | Uniform films for rapid-dissolve dosage form incorporating anti-tacking compositions |
US11191737B2 (en) | 2016-05-05 | 2021-12-07 | Aquestive Therapeutics, Inc. | Enhanced delivery epinephrine compositions |
US11207805B2 (en) | 2001-10-12 | 2021-12-28 | Aquestive Therapeutics, Inc. | Process for manufacturing a resulting pharmaceutical film |
US11273131B2 (en) | 2016-05-05 | 2022-03-15 | Aquestive Therapeutics, Inc. | Pharmaceutical compositions with enhanced permeation |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20060073190A1 (en) * | 2004-09-30 | 2006-04-06 | Carroll Thomas J | Sealed, edible film strip packets and methods of making and using them |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5614217A (en) * | 1995-06-07 | 1997-03-25 | R.P. Scherer Corporation | Capsule shell formulation to produce brittle capsules |
WO1999040156A1 (en) * | 1998-02-06 | 1999-08-12 | Union Carbide Chemicals & Plastics Technology Corporation | Alkylene oxide polymer compositions |
-
2001
- 2001-04-17 AU AU2001255429A patent/AU2001255429A1/en not_active Abandoned
- 2001-04-17 CA CA002416257A patent/CA2416257A1/en not_active Abandoned
- 2001-04-17 MX MXPA03000624A patent/MXPA03000624A/en unknown
- 2001-04-17 EP EP01928586A patent/EP1305011A1/en not_active Withdrawn
- 2001-04-17 JP JP2002513447A patent/JP2004504445A/en active Pending
- 2001-04-17 KR KR10-2003-7000858A patent/KR20030023709A/en not_active Application Discontinuation
- 2001-04-17 BR BR0112599-0A patent/BR0112599A/en not_active Application Discontinuation
- 2001-04-17 WO PCT/US2001/012459 patent/WO2002007711A1/en not_active Application Discontinuation
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5614217A (en) * | 1995-06-07 | 1997-03-25 | R.P. Scherer Corporation | Capsule shell formulation to produce brittle capsules |
WO1999040156A1 (en) * | 1998-02-06 | 1999-08-12 | Union Carbide Chemicals & Plastics Technology Corporation | Alkylene oxide polymer compositions |
Cited By (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10888499B2 (en) | 2001-10-12 | 2021-01-12 | Aquestive Therapeutics, Inc. | Thin film with non-self-aggregating uniform heterogeneity and drug delivery systems made therefrom |
US8906277B2 (en) | 2001-10-12 | 2014-12-09 | Monosol Rx, Llc | Process for manufacturing a resulting pharmaceutical film |
US11207805B2 (en) | 2001-10-12 | 2021-12-28 | Aquestive Therapeutics, Inc. | Process for manufacturing a resulting pharmaceutical film |
US8900498B2 (en) | 2001-10-12 | 2014-12-02 | Monosol Rx, Llc | Process for manufacturing a resulting multi-layer pharmaceutical film |
US11077068B2 (en) | 2001-10-12 | 2021-08-03 | Aquestive Therapeutics, Inc. | Uniform films for rapid-dissolve dosage form incorporating anti-tacking compositions |
US9108340B2 (en) | 2001-10-12 | 2015-08-18 | Monosol Rx, Llc | Process for manufacturing a resulting multi-layer pharmaceutical film |
US9855221B2 (en) | 2001-10-12 | 2018-01-02 | Monosol Rx, Llc | Uniform films for rapid-dissolve dosage form incorporating anti-tacking compositions |
US10285910B2 (en) | 2001-10-12 | 2019-05-14 | Aquestive Therapeutics, Inc. | Sublingual and buccal film compositions |
US8900497B2 (en) | 2001-10-12 | 2014-12-02 | Monosol Rx, Llc | Process for making a film having a substantially uniform distribution of components |
US8765167B2 (en) | 2001-10-12 | 2014-07-01 | Monosol Rx, Llc | Uniform films for rapid-dissolve dosage form incorporating anti-tacking compositions |
US9931305B2 (en) | 2001-10-12 | 2018-04-03 | Monosol Rx, Llc | Uniform films for rapid dissolve dosage form incorporating taste-masking compositions |
US8652378B1 (en) | 2001-10-12 | 2014-02-18 | Monosol Rx Llc | Uniform films for rapid dissolve dosage form incorporating taste-masking compositions |
US10111810B2 (en) | 2002-04-11 | 2018-10-30 | Aquestive Therapeutics, Inc. | Thin film with non-self-aggregating uniform heterogeneity and drug delivery systems made therefrom |
US10821074B2 (en) | 2009-08-07 | 2020-11-03 | Aquestive Therapeutics, Inc. | Sublingual and buccal film compositions |
US10272607B2 (en) | 2010-10-22 | 2019-04-30 | Aquestive Therapeutics, Inc. | Manufacturing of small film strips |
US11191737B2 (en) | 2016-05-05 | 2021-12-07 | Aquestive Therapeutics, Inc. | Enhanced delivery epinephrine compositions |
US11273131B2 (en) | 2016-05-05 | 2022-03-15 | Aquestive Therapeutics, Inc. | Pharmaceutical compositions with enhanced permeation |
Also Published As
Publication number | Publication date |
---|---|
JP2004504445A (en) | 2004-02-12 |
MXPA03000624A (en) | 2003-09-05 |
AU2001255429A1 (en) | 2002-02-05 |
KR20030023709A (en) | 2003-03-19 |
BR0112599A (en) | 2003-07-01 |
EP1305011A1 (en) | 2003-05-02 |
CA2416257A1 (en) | 2002-01-31 |
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