USRE42096E1 - Oral pulsed dose drug delivery system - Google Patents

Oral pulsed dose drug delivery system Download PDF

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USRE42096E1
USRE42096E1 US11/091,011 US9101105A USRE42096E US RE42096 E1 USRE42096 E1 US RE42096E1 US 9101105 A US9101105 A US 9101105A US RE42096 E USRE42096 E US RE42096E
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pharmaceutically active
enteric
amphetamine salts
release coating
active amphetamine
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Beth A. Burnside
Xiaodi Guo
Kimberly Fiske
Richard A. Couch
Rong-Kun Chang
Donald J. Treacy
Charlotte M. McGuiness
Edward M. Rudnic
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Shire LLC
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Shire LLC
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/48Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/5005Wall or coating material
    • A61K9/5021Organic macromolecular compounds
    • A61K9/5026Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/13Amines
    • A61K31/135Amines having aromatic rings, e.g. ketamine, nortriptyline
    • A61K31/137Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/48Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/5005Wall or coating material
    • A61K9/5021Organic macromolecular compounds
    • A61K9/5036Polysaccharides, e.g. gums, alginate; Cyclodextrin
    • A61K9/5042Cellulose; Cellulose derivatives, e.g. phthalate or acetate succinate esters of hydroxypropyl methylcellulose
    • A61K9/5047Cellulose ethers containing no ester groups, e.g. hydroxypropyl methylcellulose
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/48Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/5073Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals having two or more different coatings optionally including drug-containing subcoatings
    • A61K9/5078Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals having two or more different coatings optionally including drug-containing subcoatings with drug-free core

Abstract

A multiple pulsed dose drug delivery system for pharmaceutically active amphetamine salts, comprising an immediate-release component and an enteric delayed-release component wherein (1) the enteric release coating has a defined minimum thickness and/or (2) there is a protective layer between the pharmaceutically active amphetamine salt and the enteric release coating and/or (3) there is a protective layer over the enteric release coating. The product can be composed of either one of a number of beads in a dosage form, including either capsule, tablet, or sachet method for administering the beads.

Description

This invention pertains to a multiple dosage form delivery system comprising one or more amphetamine salts for administering the amphetamine salts to a recipient.

BACKGROUND OF THE INVENTION

Traditionally, drug delivery systems have focused on constant/sustained drug output with the objective of minimizing peaks and valleys of drug concentrations in the body to optimize drug efficacy and to reduce adverse effects. A reduced dosing frequency and improved patient compliance can also be expected for the controlled/sustained release drug delivery systems, compared to immediate release preparations. However, for certain drugs, sustained release delivery is not suitable and is affected by the following factors:

First pass metabolism: Some drugs, such as β blockers, β-estradiol, and salicylamide, undergo extensive first pass metabolism and require fast drug input to saturate metabolizing enzymes in order to minimize pre-systemic metabolism. Thus, a constant/sustained oral method of delivery would result in reduced oral bioavailability.

Biological tolerance: Continuous release drug plasma profiles are often accompanied by a decline in the pharmacotherapeutic effect of the drug, e.g., biological tolerance of transdermal nitroglycerin.

Chronopharmacology and circadian rhythms: Circadian rhythms in certain physiological functions are well established. It has been recognized that many symptoms and onset of disease occur during specific time periods of the 24 hour day, e.g., asthma and angina pectoris attacks are most frequently in the morning hours (1,2).

Local therapeutic need: For the treatment of local disorders such as inflammatory bowel disease, the delivery of compounds to the site of inflammation with no loss due to absorption in the small intestine is highly desirable to achieve the therapeutic effect and to minimize side effects.

Gastric irritation or drug instability in gastric fluid: For compounds with gastric irritation or chemical instability in gastric fluid, the use of a sustained release preparation may exacerbate gastric irritation and chemical instability in gastric fluid.

Drug absorption differences in various gastrointestinal segments: In general, drug absorption is moderately slow in the stomach, rapid in the small intestine, and sharply declining in the large intestine. Compensation for changing absorption characteristics in the gastrointestinal tract may be important for some drugs. For example, it is rational for a delivery system to pump out the drug much faster when the system reaches the distal segment of the intestine, to avoid the entombment of the drug in the feces.

Pulsed dose delivery systems, prepared as either single unit or multiple unit formulations, and which are capable of releasing the drug after a predetermined time, have been studied to address the aforementioned problematic areas for sustained release preparations. These same factors are also problematic in pulsed dose formulation development. For example, gastrointestinal transit times vary not only from patient to patient but also within patients as a result of food intake, stress, and illness; thus a single-unit pulsed-release system may give higher variability compared to a multiple unit system. Additionally, drug layering or core making for multiple unit systems is a time-consuming and hard-to-optimize process. Particularly challenging for formulation scientists has been overcoming two conflicting hurdles for pulsatile formulation development, i.e., lag time and rapid release.

Various enteric materials, e.g., cellulose acetate phthalate, hydroxypropyl methylcellulose phthalate, polyvinyl acetate phthalate, and the EUDRAGIT® acrylic polymers, have been used as gastroresistant, enterosoluble coatings for single drug pulse release in the intestine (3). The enteric materials, which are soluble at higher pH values, are frequently used for colon-specific delivery systems. Due to their pH-dependent attributes and the uncertainty of gastric retention time, in-vivo performance as well as inter- and intra-subject variability are major issues for using enteric coated systems as a time-controlled release of drugs.

A retarding swellable hydrophilic coating has been used for oral delayed release systems (4,5). It was demonstrated that lag time was linearly correlated with coating weight gain and drug release was pH independent.

Hydroxypropyl methylcellulose barriers with erodible and/or gellable characteristics formed using press coating technology for tablet dosage forms have been described to achieve time-programmed release of drugs (6). Barrier formulation variables, such as grade of hydroxypropyl methylcellulose, water-soluble and water-insoluble excipients, significantly altered the lag time and the release rate from the center cores.

Special grades of hydroxypropyl methylcellulose, e.g., METOLOSE® 60SH, 90SH (Shin-Etsu Ltd., Japan), and METHOCEL® F4M (Dow Chemical Company, USA), as a hydrophilic matrix material have been used to achieve bimodal drug release for several drugs, i.e., aspirin, ibuprofen, and adinazolam (7). Bimodal release is characterized by a rapid initial release, followed by a period of constant release, and finalized by a second rapid drug release.

Tablets or capsules coated with a hydrophobic wax-surfactant layer, made from an aqueous dispersion of carnauba wax, beeswax, polyoxyethylene sorbitan monooleate, and hydroxypropyl methylcellulose have been used for rapid drug release after a predetermined lag time. For example,. However, even though a two-hour lag time was achieved for the model drug theophylline at a higher coating level (60%), three hours were required for a complete release of theophylline after the lag time. (8)

A sustained-release drug delivery system is described in U.S. Pat. No. 4,871,549. When this system is placed into dissolution medium or the gastrointestinal tract, water influx and the volume expansion of the swelling agent cause the explosion of the water permeable membrane. The drug thus releases after a predetermined time period.

The OROS® push-pull system (Alza Company) has been developed for pulsatile delivery of water-soluble and water-insoluble drugs ( a specific site (e.g., colon) in the gastrointestinal tract (11). The drug formulation is contained within a water-insoluble capsule body and is sealed with a hydrogel plug. Upon oral administration, the capsule cap dissolves in the gastric juice and the hydrogel plug swells. At a controlled and predetermined time point, the swollen plug is ejected from the PULSINCAP® dosage form and the encapsulated drug is released. A pulsatile capsule system containing captopril with release after a nominal 5-hr period was found to perform reproducibly in dissolution and gamma scintigraphy studies. However, in the majority of subjects, no measurable amounts of the drug were observed in the blood, possibly due to instability of the drug in the distal intestine. (12)

ADDERAL® comprises a mixture of four amphetamine sulfate salts which, in combination is indicated for treatment of Attention Deficit of age. One disadvantage of current treatment is that a tablet form is commonly used which many young children have difficulty in swallowing. Another disadvantage of current treatments is that two separate doses are administered, one in the morning and one approximately 4-6 hours later, commonly away from home under other than parental supervision. This current form of treatment, therefore, requires a second treatment which is time-consuming, inconvenient and may be problematic for those children having difficulties in swallowing table t formulations.

SUMMARY OF THE INVENTION

Accordingly, in view of a need for successfully administering a multiple pulsed dose of amphetamine salts and mixtures thereof, the present invention provides an oral multiple pulsed dose delivery system for amphetamine salts and mixtures thereof. FIG. 1 illustrates the desired target plasma level profile of the pharmaceutical active contained within the delivery system.

In accordance with a preferred embodiment of the present invention, there is provided a pharmaceutical composition for delivering one or more pharmaceutically active amphetamine salts that includes:

    • (a) one or more pharmaceutically active amphetamine salts that are covered with an immediate release coating, and
    • (b) one or more pharmaceutically active amphetamine salts that are covered with an enteric release coating wherein (1) the enteric release coating has a defined minimum thickness and/or (2) there is a protective layer between the at least one pharmaceutically active amphetamine salt and the enteric release coating and/or (3) there is a protective layer over the enteric release coating.

In one embodiment, the immediate release and enteric release portions of the composition are present on the same core.

In another embodiment, the immediate release and enteric release components are present on different cores.

It is also contemplated that the composition may include a combination of the hereinabove referred to cores (one or more cores that include both components on the same core and one or more cores that include only one of the two components on the core).

The present invention provides a composition in which there is immediate release of drug and enteric release of drug wherein the enteric release is a pulsed release and wherein the drug includes one or more amphetamine salts and mixtures thereof.

The immediate release component releases the pharmaceutical agent in a pulsed dose upon oral administration of the delivery system.

The enteric release coating layer retards or delays the release of the pharmaceutical active or drug for a specified time period (“lag time”) until a predetermined time, at which time the release of the drug is rapid and complete, i.e., the entire dose is released within about 30-60 minutes under predetermined environmental conditions, i.e. a particular location within the gastrointestinal tract.

The delay or lag time will take into consideration factors such as transit times, food effects, inflammatory bowel disease, use of antacids or other medicaments which alter the pH of the GI tract.

In a preferred embodiment, the lag time period is only time-dependent, i.e., pH independent. The lag time is preferably within 4 to 6 hours after oral administration of the delivery system.

In one aspect, the present invention is directed to a composition that provides for enteric release of at least one pharmaceutically active amphetamine salt, including at least one pharmaceutically active amphetamine salt that is coated with an enteric coating wherein (1) the enteric release coating has a defined minimum thickness and/or (2) there is a protective layer between the at least one pharmaceutically active amphetamine salt and the enteric release coating and/or (3) there is a protective layer over the enteric release coating.

In attempting to provide for enteric release of an amphetamine salt, applicants found that use of an enteric release coating as generally practiced in the art did not provide effective enteric release.

Typical enteric coating levels did not meet the above requirements for the desired dosage profile of amphetamine salts. Using the typical amount of enteric coating (10-20 μ) resulted in undesired premature leakage of the drug from the delivery system into the upper gastrointestinal tract and thus no drug delivery at the desired location in the gastrointestinal tract after the appropriate lag time. Thus this coating did not meet the requirements for the drug release profile to provide full beneficial therapeutic activity at the desired time.

Surprisingly, applicants found that using a thicker application of enteric coating on the formulation allowed for the second pulsed dose to be released only and completely at the appropriate time in the desired predetermined area of the gastrointestinal tract, i.e., in the intestine.

Th is was surprising because an increase in thickness of about 5-10 μof enteric coatings above a minimum thickness of about 10-20 μtypically does not have a significant effect on release of d rug from within such coatings. Enteric coatings typically are pH dependent and will only dissolve/disperse when exposed to the appropriate environment. Typically, application of a thicker coating (greater than 20 μ) will only marginally increase the time for complete release at the appropriate environmental condition i.e., for a brief period of time (20 minutes). Using the typical coating, applicants could not achieve the desired result—rather, the coating leaked before the predetermined time in an inappropriate environment resulting in significant loss of the therapeutic agent.

Accordingly, in one aspect, the pulsed enteric release of the amphetamine salts is accomplished by employing a certain minimum thickness of the enteric coating .

In one embodiment of the invention, the pulsed dose delivery comprises a composition which comprises one or more pharmaceutically active amphetamine salts; an enteric coating over the one or more pharmaceutically active amphetamine salts, wherein the thickness of the enteric coating layer is at least 25 μ; a further layer of one or more pharmaceutically active amphetamine salts over the enteric coating layer; and an immediate release layer coating. The thicker enteric coating surprisingly provides the required delayed i m mediate release of the pharmaceutically active amphetamine salt at the desire d time in the desired area of the gastrointestinal tract. FIG. 2 illustrates a model of this delivery system.

In this aspect, the one or more pharmaceutically active amphetamine salts can be provided within or as a part of a core seed around which the enteric coating is applied. Alternatively, a core seed can be coated with one or more layers of one or more pharmaceutically active amphetamine salts.

It has further been discovered that a delayed immediate release drug delivery can also be accomplished by coating the drug first with a protective layer prior to applying the enteric coating.

Thus, in another embodiment, the pulsed enteric release is accomplished by employing a protective layer between the drug and the enteric coating. When using a protective coating, the enteric coating may be of an increased thickness or may be of lower thickness.

Thus, in another aspect, the object of the invention is met by providing a composition comprising one or more pharmaceutically active amphetamine salts; a protective layer coating over the one or more pharmaceutically active amphetamine salt layer(s), and an enteric coating layer over the protective coating layer; a further pharmaceutically active amphetamine salt layer and an immediate release layer coating. In a preferred embodiment of this aspect, the thickness of the enteric coating is at least 25 μ, and the protective layer comprises an immediate release coating.

With respect to this embodiment of the invention, the one or more pharmaceutically active amphetamine salts can be provided within or as a part of a core seed, during the core seed manufacturing process, around which the protective coating is applied. Alternatively, a core seed can be coated with one or more layers of one or more pharmaceutically active amphetamine salts.

In another embodiment, the pulsed enteric release is accomplished by employing a protective layer over the enteric coating.

Accordingly, in this embodiment of the present invention, there is provided a pulsed dose release drug delivery system comprising one or more pharmaceutically active amphetamine salts; an enteric coating layer over the pharmaceutically active amphetamine salt layer(s); and a protective layer over the enteric coating; a second pharmaceutically active amphetamine salt layer; and an immediate release layer coating.

In one aspect of this embodiment, the protective layer is comprised of one or more components, which includes an immediate release layer and a modifying layer. The modifying layer is preferably comprised of a semi water-permeable polymer. Applicants have surprisingly found that a semi-permeable polymer coating used in combination with an immediate release layer coating provided a delayed pulsed release drug delivery profile when layered over the enteric coating.

Thus, in this embodiment, the protective layer comprises a semi-permeable polymer and an immediate release coating layer. In a preferred embodiment, the modifying layer comprises a first layer of a semi-permeable polymer which is adjacent to the enteric coating layer and a second coating layer over the semi-permeable polymer coating layer comprising an immediate release polymer coating layer.

In one aspect of this embodiment, a semi-permeable polymer, which may comprise a low water-permeable pH-insensitive polymer, is layered onto the outer surface of the enteric layer, in order to obtain prolonged delayed release time. This semi-permeable polymer coating controls the erosion of the pH-sensitive enteric polymer in an alkaline pH environment in which a pH-sensitive polymer will dissolve rapidly. Another pH-sensitive layer may be applied onto the surface of a low water-permeability layer to further delay the release time.

In a still further aspect of the invention, in addition to a protective layer, the composition comprises an acid which is incorporated into the pharmaceutical active layer or coated onto the surface of the active layer to reduce the pH value of the environment around the enteric polymer layer. The acid layer may also be applied on the outer layer of the pH-sensitive enteric polymer layer, followed by a layer of low water-permeability polymer. The release of the active thus may be delayed and the dissolution rate may be increased in an alkaline environment.

In a further embodiment, the protective coating may be used both over the drug and over the enteric coating.

With respect to this embodiment of the invention, the one or more pharmaceutically active amphetamine salts can be provided within or as a part of a core seed, during the core seed manufacturing process, around which the enteric coating is applied. Alternatively, a core seed can be coated with one or more layers of one or more pharmaceutically active amphetamine salts.

The drug delivery system of the present invention as described herein preferably comprises one or a number of beads or beadlets in a dosage form, either capsule, tablet, sachet or other method of orally administering the beads.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 illustrates a multiple pulse drug delivery system target plasma profile of the drug delivery system of the present invention. The profile reflects an immediate-release component followed by a delayed-release component.

FIG. 2 schematically illustrates the delayed-release system of the present invention.

FIG. 2a graphically illustrates a pulsed dose delivery system.

FIGS. 2b and c graphically illustrate the drug release mechanism from the proposed delivery system.

FIG. 3 is a plot of the percent drug released versus time from the drug-loaded pellets described in Example 1 which exemplifies the immediate release component of the present invention.

FIG. 4 is a plot of the percent drug released versus time from the coated pellets described in Example 2 which exemplifies the immediate release component and the delayed release components of the present invention.

FIG. 5 is a plot of the percent drug released versus time from the coated pellets of described in Example 3 which exemplifies the immediate release component and the delayed release components of the present invention.

FIG. 6 illustrates the drug release profile of coated pellets described in Example 4 which exemplifies the immediate release component and the delayed release components of the present invention.

DETAILED DESCRIPTION OF THE INVENTION

The present invention comprises a core or starting seed, either prepared or commercially available product. The cores or starting seeds can be sugar spheres; spheres made from microcrystalline cellulose and any suitable drug crystals.

The materials that can be employed in making drug-containing pellets are any of those commonly used in pharmaceutics and should be selected on the basis of compatibility with the active drug and the physicochemical properties of the pellets. The additives except active drugs are chosen below as examples:

Binders such as cellulose derivatives such as methylcellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, hydroxypropyl methylcellulose, polyvinylpyrrolidone, polyvinylpyrrolidone/vinyl acetate copolymer and the like.

Disintegration agents such as corn starch, pregelatinized starch, cross-linked carboxymethylcellulose (AC-DI-SOL®), sodium starch glycolate (EXPLOTAB®), cross-linked polyvinylpyrrolidone (PLASDONE® XL), and any disintegration agents used in tablet preparations.

Filling agents such as lactose, calcium carbonate, calcium phosphate, calcium sulfate, microcrystalline cellulose, dextran, starches, sucrose, xylitol, lactitol, mannitol, sorbitol, sodium chloride, polyethylene glycol, and the like.

Surfactants such as sodium lauryl sulfate, sorbitan monooleate, polyoxyethylene sorbitan monooleate, bile salts, glyceryl monostearate, PLURONIC® line (BASF), and the like.

Solubilizer such as citric acid, succinic acid, fumaric acid, malic acid, tartaric acid, maleic acid, glutaric acid sodium bicarbonate and sodium carbonate and the like.

Stabilizers such as any antioxidation agents, buffers, acids, and the like, can also be utilized.

Methods of manufacturing the core include

a. Extrusion-Spheronization—Drug(s) and other additives are granulated by addition of a binder solution. The wet mass is passed through an extruder equipped with a certain size screen. The extrudates are spheronized in a marumerizer. The resulting pellets are dried and sieved for further applications.

b. High-Shear Granulation—Drug(s) and other additives are dry-mixed and then the mixture is wetted by addition of a binder solution in a high shear-granulator/mixer. The granules are kneaded after wetting by the combined actions of mixing and milling. The resulting granules or pellets are dried and sieved for further applications.

c. Solution or Suspension Layering—A drug solution or dispersion with or without a binder is sprayed onto starting seeds with a certain particle size in a fluid bed processor or other suitable equipment. The drug thus is coated on the surface of the starting seeds. The drug-loaded pellets are dried for further applications.

For purposes of the present invention, the core particles have a diameter in the range of about 500-1500 100-1500 microns; preferably 100-800 microns.

These particles can then be coated in a fluidized bed apparatus with an alternating sequence of coating layers.

The core may be coated directly with a layer or layers of at least one pharmaceutically active amphetamine salts and/or the pharmaceutically active amphetamine salt may be incorporated into the core material. Pharmaceutical active amphetamine salts contemplated to be within the scope of the present invention include amphetamine base, all chemical and chiral derivatives and salts thereof; methylphenidate, all chemical and chiral derivatives and salts thereof; phenylpropanolamine and its salts; and all other compounds indicated for the treatment of attention deficit hyperactivity disorder (ADHD).

A protective layer may be added on top of t he pharmaceutical active containing layer and also may be provided between active layers. A separation or protective layer may be added onto the surface of the active-loaded core, and then the enteric layer is coated thereupon. Another active layer may also be added to the enteric layer to deliver an initial dose.

A protective coating layer may be applied immediately outside the core, either a drug-containing core or a drug-layered core, by conventional coating techniques such as pan coating or fluid bed coating using solutions of polymers in water or suitable organic solvents or by using aqueous polymer dispersions. Suitable materials for the protective layer include cellulose derivatives such as hydroxyethyl cellulose, hydroxypropyl cellulose, hydroxypropyl methylcellulose, polyvinylpyrrolidone, polyvinylpyrrolidone/vinyl acetate copolymer, ethyl cellulose aqueous dispersions (AQUACOAT®, SURELEASE®), EUDRAGIT® RL 30D, OPADRY® and the like. The suggested coating levels are from 1 to 6%, preferably 2-4% (w/w).

The enteric coating layer is applied onto the cores with or without seal coating by conventional coating techniques, such as pan coating or fluid bed coating using solutions of polymers in water or suitable organic solvents or by using aqueous polymer dispersions. All commercially available pH-sensitive polymers are included. The pharmaceutical active is not released in the acidic stomach environment of approximately below pH 4.5, but not limited to this value. The pharmaceutical active should become available when the pH-sensitive layer dissolves at the greater pH; after a certain delayed time; or after the unit passes through the stomach. The preferred delay time is in the range of two to six hours.

Enteric polymers include cellulose acetate phthalate, Cellulose acetate trimellitate, hydroxypropyl methylcellulose phthalate, polyvinyl acetate phthalate, carboxymethylethylcellulose, co-polymerized methacrylic acid/methacrylic acid methyl esters such as, for instance, materials known under the trade name EUDRAGIT® L12.5, L100, or EUDRAGIT® S12.5, S100 or similar compounds used to obtain enteric coatings. Aqueous colloidal polymer dispersions or re-dispersions can be also applied, e.g. EUDRAGIT® L 30D-55, EUDRAGIT® L100-55, EUDRAGIT® S100, EUDRAGIT® preparation 4110D (Rohm Pharma); AQUATERIC®, AQUACOAT® CPD 30 (FMC); KOLLICOAT MAE® 30D and 30DP (BASF); EASTACRYL® 30D (Eastman Chemical).

The enteric polymers used in this invention can be modified by mixing with other known coating products that are not pH sensitive. Examples of such coating products include the neutral methacrylic acid esters with a small portion of trimethylammonioethyl methacrylate chloride, sold currently under the trade names EUDRAGIT® and EUDRAGIT® RL; a neutral ester dispersion without any functional groups, sold under the trade names EUDRAGIT® NE30D and EUDRAGIT® NE30; and other pH independent coating products.

The modifying component of the protective layer used over the enteric coating can include a water penetration barrier layer (semipermeable polymer) which can be successively coated after the enteric coating to reduce the water penetration rate through the enteric coating layer and thus increase the lag time of the drug release. Sustained-release coatings commonly known to one skilled in the art can be used for this purpose by conventional coating techniques such as pan coating or fluid bed coating using solutions of polymers in water or suitable organic solvents or by using aqueous polymer dispersions. For example, the following materials can be used, but not limited to: Cellulose acetate, Cellulose acetate butyrate, Cellulose acetate propionate, Ethyl cellulose, Fatty acids and their esters, Waxes, zein, and aqueous polymer dispersions such as EUDRAGIT® RS and RL 30D, EUDRAGIT® NE 30D, AQUACOAT®, SURELEASE®, cellulose acetate latex. The combination of above polymers and hydrophilic polymers such as Hydroxyethyl cellulose, Hydroxypropyl cellulose (KLUCEL®, Hercules Corp.), Hydroxypropyl methylcellulose (METHOCEL®, Dow Chemical Corp.), Polyvinylpyrrolidone can also be used.

An overcoating layer can further optionally be applied to the composition of the present invention. OPADRY®, OPADRY II® (Colorcon) and corresponding color and colorless grades from Colorcon can be used to protect the pellets from being tacky and provide colors to the product. The suggested levels of protective or color coating are from 1 to 6%, preferably 2-3% (w/w).

Many ingredients can be incorporated into the overcoating formula, for example to provide a quicker immediate release, such as plasticizers; acetyltriethyl citrate, triethyl citrate, acetyltributyl citrate, dibutylsebacate, triacetin, polyethylene glycols, propylene glycol and the others; lubricants: talc, colloidal silica dioxide, magnesium stearate, calcium stearate, titanium dioxide, magnesium silicate, and the like.

The composition, preferably in beadlet form, can be incorporated into hard gelatin capsules, either with additional excipients, or alone. Typical excipients to be added to a capsule formulation include, but are not limited to: fillers such as microcrystalline cellulose, soy polysaccharides, calcium phosphate dihydrate, calcium sulfate, lactose, sucrose, sorbitol, or any other inert filler. In addition, there can be flow aids such as fumed silicon dioxide, silica gel, magnesium stearate, calcium stearate or any other material imparting flow to powders. A lubricant can further be added if necessary by using polyethylene glycol, leucine, glyceryl behenate, magnesium stearate or calcium stearate.

The composition may also be incorporated into a tablet, in particular by incorporation into a tablet matrix, which rapidly disperses the particles after ingestion. In order to incorporate these particles into such a tablet, a filler/binder must be added to a table that can accept the particles, but will not allow their destruction during the tableting process. Materials that are suitable for this purpose include, but are not limited to, microcrystalline cellulose (A VICEL®), soy polysaccharide (EMCOSOY®), pre-gelatinized starches (STARCH® 1500, NATIONAL® 1551), and polyethylene glycols (CARBOWAX®). The materials should be present in the range of 5-75% (w/w), with a preferred range of 25-50% (w/w).

In addition, disintegrants are added in order to disperse the beads once the tablet is ingested. Suitable disintegrants include, but are not limited to: cross-linked sodium carboxymethyl cellulose (AC-DI-SOL®), sodium starch glycolate (EXPLOTAB®, PRIMOJEL®), and cross-linked polyvinylpolypyrrolidone (Plasone-XL). These materials should be present in the rate of 3-15% (w/w), with a preferred range of 5-10% (w/w).

Lubricants are also added to assure proper tableting, and these can include, but are not limited to: magnesium stearate, calcium stearate, stearic acid, polyethylene glycol, leucine, glyceryl behanate, and hydrogenated vegetable oil. These lubricants should be present in amounts from 0.1-10% (w/w), with a preferred range of 0.3-3.0% (w/w).

Tablets are formed, for example, as follows. The particles are introduced into a blender along with AVICEL®, disintegrants and lubricant, mixed for a set number of minutes to provide a homogeneous blend which is then put in the hopper of a tablet press with which tablets are compressed. The compression force used is adequate to form a tablet; however, not sufficient to fracture the beads or coatings.

It will be appreciated that the multiple dosage form of the present invention can deliver rapid and complete dosages of pharmaceutically active amphetamine salts to achieve the desired levels of the drug in a recipient over the course of about 8 hours with a single oral administration.

In so doing, the levels of drug in blood plasma of the pharmaceutically active amphetamine salts will reach a peak fairly rapidly after about 2 hours, and after about 4 hours a second pulse dose is released, wherein a second fairly rapid additive increase of plasma drug levels occurs which slowly decreases over the course of the next 12 hours.

The following examples are presented to illustrate and do not limit the invention.

EXAMPLES Example 1

Immediate release formulation

The following formulation was used to layer the drug onto sugar spheres. Nonpareil seeds (30/35 mesh, Paulaur Corp., NJ), 6.8 kg were put into a FLM-15 fluid bed processor with a 9″ Wurster column and fluidized at 60° C. The suspension of mixed amphetamine salts (MAS) with 1% HPMC E5 Premium (Dow Chemical) as a binder was sprayed onto the seed under suitable conditions. Almost no agglomeration and no fines were observed with a yield of at least 98%. The drug-loaded cores were used to test enteric coatings and sustained release coatings.

TABLE 1
Ingredients Amount (%)
Nonpareil seed 88.00
mixed amphetamine salts 11.40
METHOCEL ® E5 Premium  0.60
Water *
*removed during processing

The drug release profile of the drug-loaded pellets of this example is shown in FIG. 3.

Example 2

The following formulation was used to coat the mixed amphetamine salts loaded (MASL) pellets from Example 1 with the EUDRAGIT® L 30D-55 (Rohm Pharma, Germany) coating dispersion. 2 kg of MASL pellets were loaded into a fluid bed processor with a reduced Wurster column equipped with a precision coater(MP 2/3, Niro Inc.) . The coating dispersion was prepared by dispersing Triethyl citrate, Talc and EUDRAGIT® L 30D-55 into water and mixing for at least 30 minutes. Under suitable fluidization conditions, the coating dispersion was sprayed onto the fluidized MASL pellets. The spraying was continued until the targeted coating level was achieved(20μ) . The coated pellets were dried at 30-35° C. for 5 minutes before stopping the process. The enteric coated PPA MASL pellets were tested at different pH buffers by a USP paddle method. The drug content was analyzed using HPLC. The results showed that the enteric coating delayed the drug release from the coated pellets until after exposure to pH 6 or higher. (Reference # AR98I25-4)

TABLE 2
Ingredients Amount (%)
MASL pellets 40.0070.00
EUDRAGIT ® L 30D-55 24.88 
Triethyl citrate 2.52
Talc 2.60
Water *
*removed during processing

The drug release profile of the coated pellets of this example is shown in FIG. 4.

Example 3

The following formulation was used to coat the MASL pellets from Example 1 with the EUDRAGIT® 4110D (Rohm Pharma, Germany) coating dispersion. MASL pellets (2 kg) were loaded in a fluid bed processor with a reduced Wurster column (GPGC-15 Glatt). The coating dispersion was prepared by dispersing Triethyl citrate, Talc and EUDRAGIT® 4110D into water and mixing for at least 30 minutes. Under suitable fluidization conditions, the coating dispersion was sprayed onto the fluidized MASL pellets. The spraying was continued until the targeted coating level was achieved. The coated pellets were dried at 30-35° C. for 5 minutes before stopping the process. The enteric coated MASL pellets were tested u sing a USP paddle method at different pH buffers. The drug content was analyzed using HPLC. The enteric coating delayed the drug release for several hours from the coated pellets until the pH value reached 6.8 or higher. (Reference # AR98I25-3)

TABLE 3
Ingredients Amount (%)
MASL pellets 70.00
EUDRAGIT ® 4110D 26.24
Triethyl citrate 0.76
Talc 3.00
Water *
*removed during processing

The drug release profile of coated pellets of this example is shown in FIG. 5.

Example 4

The following formulation was selected to coat the enteric coated MASL pellets. Coated MASL pellets from Example 2 or coated MASL pellets from Example 3 (2 kg of either) were loaded into a fluid bed processor with a reduced Wurster column (GPGC-1 5, Glatt). The coating dispersion was prepared by mixing SURELEASE® (Colorcon) and water for at least 15 minutes prior to spraying. Under suitable fluidization conditions, the coating dispersion was sprayed onto the fluidized pellets. The spraying was continued until the targeted coating level was achieved. The coated pellets were coated with a thin layer of OPADRY® white (Colorcon) (2%) to prevent the tackiness of the coated pellets during storage. The coated pellets were then dried at 35-40° C. for 10 minutes before discharging from the bed. The drug dissolution from both coated pellets was performed using a USP paddle method at different pH buffers. The drug content was analyzed using HPLC. The 8% SURELEASE® coating slightly sustained the drug release from EUDRAGIT® L 30D-55 coated pellets at pH 7.5 buffer, while the SURELEASE® coating delayed the drug release up to 2 hours after the buffer switched from pH 1 to pH 7.5. (Reference ## AR98I25-1)

TABLE 4
Ingredients Amount, kg (%)
Enteric coated MASL pellets 90.00 
SURLEASE ® 8.00
OPADRY ® white 2.00
Water *
*removed during processing

The drug release profile of the coated pellets from this example is shown in FIG. 6.

CITED LITERATURE

1. B.Lemmer, “Circadian Rhythms and Drug Delivery”, J. Controlled Release, 16, 63-74 (1991)

2. B. Lemmer, “Why are so many Biological Systems Periodic?” in Pulsatile Drug Delivery: Current Applications and Future Trends, R Gumy, HE Junginger and NA Peppas, eds. (Wissenschaftliche Verlagsgesellschaft mbH Stuttgart, Germany 1993) pp.11-24

3. X. Xu and PI Lee, “Programmable Drug Delivery from an Erodible Association Polymer System”, Pharm. Res. 10(8), 1144-1152 (1993)

4. A. Gazzaniga, ME Sangalli, and F Giodano, “Oral Chonotropic Drug Delivery Systems: Achievement of Time and/or Site Specificity”, Eur J Pharm. Biopharm., 40(4), 246-250 (1994)

5. A Gazzaniga, C Busetti, L Moro, ME Sangalli and F Giordano, “Time Dependent Oral Delivery Systems for Colon Targeting”, S. T.P. Pharma Sciences5(1), 83-88 (1996)

6. U Conte, L Maggi, ML Torre, P Giunchedi and A Lamanna, “Press-coated Tablets for Time programmed Release of Drugs”, Biomaterials, 14(13), 1017-1023 (1993)

7. AC Shah International Patent Application W098/00044

8. PS Walia, P Jo Mayer Stout and R Turton, “Preliminary Evaluation of an Aqueous Wax Emulsion for Controlled Release Coating”, Pharm Dev Tech, 3(1), 103-113 (1998)

9. F Theeuwes, “OROS® Osmotic System Development”, Drug Dev Ind Pharm9(7), 1331-1357 (1983)

10. F Theeuwes, “Triggered, Pulsed and Programmed Drug Delivery” in Novel Drug Delivery and its Therapeutic Application, LF Prescott and WS Nimmos. eds. (Wiley, New York, 1989) pp. 323-340

11. M McNeil, A Rashid and H Stevens, “International Patent App W090/09168

12. IR Wilding, SS Davis, M Bakhshaee, HNE Stevens, RA Sparrow and J Brennan, “Gastrointestinal Transit and Systemic Absorption of Captopril from a Pulsed Release Formulation”, Pharm Res 9(5), 654-657 (1992)

Claims (25)

1. A pharmaceutical composition for delivery of one or more pharmaceutically active amphetamine salts, comprising:
(a) one or more pharmaceutically active amphetamine salts covered with an immediate release coating; and
(b) one or more pharmaceutically active amphetamine salts that are covered with an enteric release coating that provides for delayed pulsed enteric release, wherein said enteric release coating releases essentially all of said one or more pharmaceutically active amphetamine salts coated with said enteric coating within about 60 minutes after initiation of said delayed pulsed enteric release release;
wherein the pharmaceutically active amphetamine salts in (a) and (b) comprise mixed amphetamine salts.
2. The composition of claim 1 A pharmaceutical composition for delivery of one or more pharmaceutically active amphetamine salts, comprising:
(a) one or more pharmaceutically active amphetamine salts covered with an immediate release coating; and
(b) one or more pharmaceutically active amphetamine salts that are covered with an enteric release coating that provides for delayed pulsed enteric release, wherein said enteric release coating releases essentially all of said one or more pharmaceutically active amphetamine salts coated with said enteric coating within about 60 minutes after initiation of said delayed pulsed enteric release; wherein said enteric release coating has a thickness of at least 25μ.
3. The pharmaceutical composition of claim 1 wherein the one or more pharmaceutically active amphetamine salts are coated onto a core.
4. The pharmaceutical composition of claim 1 wherein the one or more pharmaceutically active amphetamine salts are incorporated into a core.
5. The pharmaceutical composition of claim 1 A pharmaceutical composition for delivery of one or more pharmaceutically active amphetamine salts, comprising:
(a) one or more pharmaceutically active amphetamine salts covered with an immediate release coating; and
(b) one or more pharmaceutically active amphetamine salts that are covered with an enteric release coating that provides for delayed pulsed enteric release, wherein said enteric release coating releases essentially all of said one or more pharmaceutically active amphetamine salts coated with said enteric coating within about 60 minutes after initiation of said delayed pulsed enteric release; wherein the one or more pharmaceutically active amphetamine salts covered with an immediate release coating and the one or more pharmaceutically active amphetamine salts covered with an enteric release coating are present on a single core.
6. The pharmaceutical composition of claim 1 wherein the one or more pharmaceutically active amphetamine salts covered with an immediate release coating and the one or more pharmaceutically active amphetamine salts covered with an enteric release coating are present on different cores.
7. The composition of claim 1 wherein said enteric release coating is a non-pH dependent enteric release coating.
8. A pharmaceutical composition for delivery of at least one amphetamine salt, comprising:
(a) at least one pharmaceutically active amphetamine salt covered with an immediate release coating; and
(b) at least one pharmaceutically active amphetamine salt covered with an enteric release coating, said component (a) providing for an immediate release of amphetamine salt to provide a first blood level of amphetamine salt and component (b) providing a delayed pulse enteric release of amphetamine salt that increases the blood level of amphetamine salt to a second level that is greater than the first level provided by component (a), wherein said enteric release coating releases essentially all of said one or more pharmaceutically active amphetamine salts coated with said enteric coating within about 60 minutes after initiation of said delayed pulsed enteric release;
wherein the pharmaceutically active amphetamine salts comprise mixed amphetamine salts in (a) and (b) comprise mixed amphetamine salts.
9. The pharmaceutical composition of claim 8 wherein the one or more pharmaceutically active amphetamine salts are coated onto a core.
10. The pharmaceutical composition of claim 8 wherein the one or more pharmaceutically active amphetamine salts are incorporated into a core.
11. The pharmaceutical composition of claim 8 A pharmaceutical composition for delivery of at least one amphetamine salt, comprising:
(a) at least one pharmaceutically active amphetamine salt covered with an immediate release coating; and
(b) at least one pharmaceutically active amphetamine salt covered with an enteric release coating, said component (a) providing for an immediate release of amphetamine salt to provide a first blood level of amphetamine salt and component (b) providing a delayed pulse enteric release of amphetamine salt that increases the blood level of amphetamine salt to a second level that is greater than the first level provided by component (a), wherein said enteric release coating releases essentially all of said one or more pharmaceutically active amphetamine salts coated with said enteric coating within about 60 minutes after initiation of said delayed pulsed enteric release; and wherein the one or more pharmaceutically active amphetamine salts covered with an immediate release coating and the one or more pharmaceutically active amphetamine salts covered with an enteric release coating are present on a single core.
12. The pharmaceutical composition of claim 8 wherein the one or more pharmaceutically active amphetamine salts covered with an immediate release coating and the one or more pharmaceutically active amphetamine salts covered with an enteric release coating are present on different cores.
13. A pharmaceutical composition for delivering one or more pharmaceutically active amphetamine salts comprising:
(a) one or more pharmaceutically active amphetamine salts covered with an immediate release coating;
(b) one or more pharmaceutically active amphetamine salts that are covered with an enteric release coating that provides for delayed pulsed enteric release, wherein said enteric release coating releases essentially all of said one or more pharmaceutically active amphetamine salts coated with said enteric coating within about 60 minutes after initiation of said delayed pulsed enteric release; and
(c) a protective layer over the enteric release coating.
14. The pharmaceutical composition of claim 13 wherein the one or more pharmaceutically active amphetamine salts are coated onto a core.
15. The pharmaceutical composition of claim 13 wherein the one or more pharmaceutically active amphetamine salts are incorporated into a core.
16. The pharmaceutical composition of claim 13 wherein the one or more pharmaceutically active amphetamine salts covered with an immediate release coating and the one or more pharmaceutically active amphetamine salts covered with an enteric release coating are present on a single core.
17. The pharmaceutical composition of claim 13 wherein the one or more pharmaceutically active amphetamine salts covered with an immediate release coating and the one or more pharmaceutically active amphetamine salts covered with an enteric release coating are present On on different cores.
18. A pharmaceutical composition for delivery of one or more pharmaceutically active amphetamine salts comprising:
(a) one or more pharmaceutically active amphetamine salts covered with an immediate release coating;
(b) one or more pharmaceutically active amphetamine salts that are covered with an enteric release coating that provides for delayed pulsed enteric release, wherein said enteric release coating releases said one or more pharmaceutically active amphetamine salts coated with said enteric coating within about 60 minutes after initiation of said delayed pulsed enteric release; and
(c) a protective layer between the at least one pharmaceutically active amphetamine salt and the enteric release coating.
19. The pharmaceutical composition of claim 18 wherein The delayed pulsed release is from 4 to 6 hours after administration of the pharmaceutical composition.
20. The pharmaceutical composition of claim 18 wherein the delayed pulse enteric release, releases the amphetamine salt in about 30 to 60 minutes after initiation of the release.
21. The pharmaceutical composition of claim 18 wherein the one or more pharmaceutically active amphetamine salts are coated onto a core.
22. The pharmaceutical composition of claim 18 wherein the one or more pharmaceutically active amphetamine salts are incorporated into a core.
23. The pharmaceutical composition of claim 18 wherein the one or more pharmaceutically active amphetamine salts covered with an immediate release coating and the one or more pharmaceutically active amphetamine salts covered with an enteric release coating are present on a single core.
24. The pharmaceutical composition of claim 18 wherein the one or more pharmaceutically active amphetamine salts covered with an immediate release coating and the one or more pharmaceutically active amphetamine salts covered with an enteric release coating are present on different cores.
25. The pharmaceutical composition of any one of claims 2, 13 or 18 to 20 wherein the pharmaceutically active amphetamine salt in (a) and (b) comprises mixed amphetamine salts.
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US09/807,462 Expired - Lifetime US6605300B1 (en) 1998-10-21 1999-10-20 Oral pulsed dose drug delivery system
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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9545399B2 (en) 2012-08-15 2017-01-17 Tris Pharma, Inc. Methylphenidate extended release chewable tablet
US9675704B2 (en) 2006-03-16 2017-06-13 Tris Pharma, Inc. Modified release formulations containing drug-ion exchange resin complexes
US9974752B2 (en) 2014-10-31 2018-05-22 Purdue Pharma Methods and compositions particularly for treatment of attention deficit disorder

Families Citing this family (178)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20010055613A1 (en) * 1998-10-21 2001-12-27 Beth A. Burnside Oral pulsed dose drug delivery system
US20090149479A1 (en) * 1998-11-02 2009-06-11 Elan Pharma International Limited Dosing regimen
DE19855421C2 (en) * 1998-11-02 2001-09-20 Alcove Surfaces Gmbh implant
AT411011T (en) * 1998-11-02 2008-10-15 Elan Pharma Int Ltd Multiparticulate composition of methylphenidate with modified release
US20060240105A1 (en) * 1998-11-02 2006-10-26 Elan Corporation, Plc Multiparticulate modified release composition
US20030170181A1 (en) * 1999-04-06 2003-09-11 Midha Kamal K. Method for preventing abuse of methylphenidate
BR0013825A (en) * 1999-08-31 2002-07-23 Gruenenthal Chemie tramadol presentation forms
US10179130B2 (en) 1999-10-29 2019-01-15 Purdue Pharma L.P. Controlled release hydrocodone formulations
AU764453B2 (en) 1999-10-29 2003-08-21 Euro-Celtique S.A. Controlled release hydrocodone formulations
CA2389568A1 (en) * 1999-11-22 2001-05-31 Alza Corporation Osmotic dosage form comprising first and second coats
DK1248594T3 (en) * 2000-01-19 2006-02-06 Mannkind Corp Formulation of multi-peak release drug delivery
US6544555B2 (en) 2000-02-24 2003-04-08 Advancis Pharmaceutical Corp. Antibiotic product, use and formulation thereof
US7674480B2 (en) * 2000-06-23 2010-03-09 Teva Pharmaceutical Industries Ltd. Rapidly expanding composition for gastric retention and controlled release of therapeutic agents, and dosage forms including the composition
US6500457B1 (en) * 2000-08-14 2002-12-31 Peirce Management, Llc Oral pharmaceutical dosage forms for pulsatile delivery of an antiarrhythmic agent
US20020068078A1 (en) 2000-10-13 2002-06-06 Rudnic Edward M. Antifungal product, use and formulation thereof
KR100960200B1 (en) 2000-10-30 2010-05-27 유로-셀티크 소시에떼 아노뉨 Controlled release hydrocodone formulations
CA2440641A1 (en) 2001-03-13 2002-09-19 Anand R. Baichwal Chronotherapeutic dosage forms containing glucocorticosteroid
NZ529308A (en) * 2001-04-05 2005-03-24 Collagenex Pharm Inc Tetracycline compounds comprising a tetracycline and a controlled release agent to provide delivery at a dose below that required for antibiotic activity
US20020187192A1 (en) * 2001-04-30 2002-12-12 Yatindra Joshi Pharmaceutical composition which reduces or eliminates drug abuse potential
AR034813A1 (en) * 2001-07-20 2004-03-17 Novartis Ag pharmaceutical compositions and use thereof
US7807197B2 (en) 2002-09-28 2010-10-05 Mcneil-Ppc, Inc. Composite dosage forms having an inlaid portion
US20040253312A1 (en) * 2001-09-28 2004-12-16 Sowden Harry S. Immediate release dosage form comprising shell having openings therein
US7838026B2 (en) 2001-09-28 2010-11-23 Mcneil-Ppc, Inc. Burst-release polymer composition and dosage forms comprising the same
US6837696B2 (en) * 2001-09-28 2005-01-04 Mcneil-Ppc, Inc. Apparatus for manufacturing dosage forms
US7122143B2 (en) 2001-09-28 2006-10-17 Mcneil-Ppc, Inc. Methods for manufacturing dosage forms
US20040146559A1 (en) * 2002-09-28 2004-07-29 Sowden Harry S. Dosage forms having an inner core and outer shell with different shapes
US20030228368A1 (en) * 2001-09-28 2003-12-11 David Wynn Edible solid composition and dosage form
EP1429724B1 (en) 2001-09-28 2013-11-06 McNeil-PPC, Inc. Dosage form containing a confectionery composition
US8679533B2 (en) 2002-07-25 2014-03-25 Pharmacia Corporation Pramipexole once-daily dosage form
US6913768B2 (en) * 2002-09-24 2005-07-05 Shire Laboratories, Inc. Sustained release delivery of amphetamine salts
US20040062778A1 (en) * 2002-09-26 2004-04-01 Adi Shefer Surface dissolution and/or bulk erosion controlled release compositions and devices
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
US7988993B2 (en) * 2002-12-09 2011-08-02 Andrx Pharmaceuticals, Inc. Oral controlled release dosage form
ES2350689T3 (en) * 2002-12-13 2011-01-26 Durect Corporation Oral delivery system comprising drugs liquid vehicle materials high viscosity.
WO2004056337A2 (en) * 2002-12-18 2004-07-08 Pain Therapeutics Oral dosage forms with therapeutically active agents in controlled release cores and immediate release gelatin capsule coats
US20040208931A1 (en) * 2002-12-30 2004-10-21 Friend David R Fast dissolving films for oral administration of drugs
AT372112T (en) * 2003-02-10 2007-09-15 Shire Biochem Inc Enantiomers amphetamine-containing compositions for the treatment of attention deficit / hyperactivity disorder (ADHD)
US20040186180A1 (en) 2003-03-21 2004-09-23 Gelotte Cathy K. Non-steroidal anti-inflammatory drug dosing regimen
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
ES2391385T3 (en) * 2003-04-07 2012-11-23 Supernus Pharmaceuticals, Inc. Formulations in single daily dose doxycycline
EP2112920B1 (en) 2003-06-26 2018-07-25 Intellipharmaceutics Corp. Proton pump-inhibitor-containing capsules which comprise subunits differently structured for a delayed release of the active ingredient
CA2533358C (en) 2003-07-21 2014-03-11 Advancis Pharmaceutical Corporation Antibiotic product, use and formulation thereof
US8313776B2 (en) 2003-07-21 2012-11-20 Shionogi Inc. Antibiotic product, use and formulation thereof
JP2006528190A (en) 2003-07-21 2006-12-14 アドバンシス ファーマスーティカル コーポレイション Antibiotics, their use and creating
DE10336400A1 (en) 2003-08-06 2005-03-24 Grünenthal GmbH Abuse-proofed dosage form
EP1653925A1 (en) 2003-08-11 2006-05-10 Advancis Pharmaceutical Corporation Robust pellet
WO2005016278A2 (en) 2003-08-12 2005-02-24 Advancis Pharmaceuticals Corporation Antibiotic product, use and formulation thereof
EP1658034A4 (en) 2003-08-29 2011-06-22 Middlebrook Pharmaceuticals Inc Antibiotic product, use and formulation thereof
WO2005027877A1 (en) 2003-09-15 2005-03-31 Advancis Pharmaceutical Corporation Antibiotic product, use and formulation thereof
US10213387B2 (en) 2003-09-19 2019-02-26 Sun Pharma Advanced Research Company Ltd. Oral drug delivery system
US10226428B2 (en) 2003-09-19 2019-03-12 Sun Pharma Advanced Research Company Ltd. Oral drug delivery system
JP2007505921A (en) 2003-09-19 2007-03-15 ペンウェスト ファーマシューティカルズ カンパニー Delayed release dosage form
JP5666075B2 (en) * 2003-09-19 2015-02-12 サン・ファーマシューティカル・インダストリーズ・リミテッドSun Pharmaceutical Industries Limited Oral drug delivery system
US20050069590A1 (en) * 2003-09-30 2005-03-31 Buehler Gail K. Stable suspensions for medicinal dosages
US20050074514A1 (en) * 2003-10-02 2005-04-07 Anderson Oliver B. Zero cycle molding systems, methods and apparatuses for manufacturing dosage forms
CA2537103C (en) * 2003-11-04 2010-01-19 Shire Laboratories, Inc. Once daily dosage forms of trospium
WO2005044238A1 (en) * 2003-11-07 2005-05-19 Ranbaxy Laboratories Limited Modified release solid dosage form of amphetamine salts
DE10353186A1 (en) * 2003-11-13 2005-06-16 Röhm GmbH & Co. KG A multilayer pharmaceutical form comprising a modulating effect in relation to active ingredient delivery substance
US7879354B2 (en) 2004-01-13 2011-02-01 Mcneil-Ppc, Inc. Rapidly disintegrating gelatinous coated tablets
US8067029B2 (en) * 2004-01-13 2011-11-29 Mcneil-Ppc, Inc. Rapidly disintegrating gelatinous coated tablets
JP2005239696A (en) * 2004-01-30 2005-09-08 Daiichi Suntory Pharma Co Ltd Medicinal hard capsule preparation blended with inorganic substance
US20050196448A1 (en) * 2004-03-05 2005-09-08 Hai Yong Huang Polymeric compositions and dosage forms comprising the same
US20050196442A1 (en) * 2004-03-05 2005-09-08 Huang Hai Y. Polymeric compositions and dosage forms comprising the same
US20050196447A1 (en) * 2004-03-05 2005-09-08 Huang Hai Y. Polymeric compositions and dosage forms comprising the same
US20050196446A1 (en) * 2004-03-05 2005-09-08 Huang Hai Y. Polymeric compositions and dosage forms comprising the same
US20050265955A1 (en) * 2004-05-28 2005-12-01 Mallinckrodt Inc. Sustained release preparations
TWI354569B (en) * 2004-05-28 2011-12-21 Squibb Bristol Myers Co Coated tablet formulation and method
WO2005117697A2 (en) * 2004-05-28 2005-12-15 Narayanan Ramasubramanian Unified indigestion package and process for patient compliance with prescribed medication regimen
US8394409B2 (en) 2004-07-01 2013-03-12 Intellipharmaceutics Corp. Controlled extended drug release technology
EP1771158A4 (en) 2004-07-02 2008-03-12 Advancis Pharmaceutical Corp Tablet for pulsed delivery
WO2006015943A2 (en) 2004-08-13 2006-02-16 Boehringer Ingelheim International Gmbh Extended release pellet formulation containing pramipexole or a pharmaceutically acceptable salt thereof, method for manufacturing the same and use thereof
AT486588T (en) 2004-08-13 2010-11-15 Boehringer Ingelheim Int Tablets, extended release formulation of pramipexole or a pharmaceutically acceptable salt thereof, production process and use this
US9149472B2 (en) * 2004-08-31 2015-10-06 Jack William Schultz Controlled release compositions for treatment of cognitive, emotional and mental ailments and disorders
US7350479B2 (en) * 2004-09-10 2008-04-01 United States Of America As Represented By The Secretary Of The Army System and method for controlling growth of aquatic plants utilizing bio-eroding means implanted in triploid grass carp
US20080020041A1 (en) * 2004-10-19 2008-01-24 Ayres James W Enteric Coated Compositions that Release Active Ingredient(s) in Gastric Fluid and Intestinal Fluid
US20070281022A1 (en) * 2004-10-27 2007-12-06 Bunick Frank J Dosage forms having a microreliefed surface and methods and apparatus for their production
US20060087051A1 (en) * 2004-10-27 2006-04-27 Bunick Frank J Dosage forms having a microreliefed surface and methods and apparatus for their production
US20060088593A1 (en) * 2004-10-27 2006-04-27 Bunick Frank J Dosage forms having a microreliefed surface and methods and apparatus for their production
US20060088587A1 (en) * 2004-10-27 2006-04-27 Bunick Frank J Dosage forms having a microreliefed surface and methods and apparatus for their production
US20070190133A1 (en) * 2004-10-27 2007-08-16 Bunick Frank J Dosage forms having a microreliefed surface and methods and apparatus for their production
US8383159B2 (en) * 2004-10-27 2013-02-26 Mcneil-Ppc, Inc. Dosage forms having a microreliefed surface and methods and apparatus for their production
US20060088586A1 (en) * 2004-10-27 2006-04-27 Bunick Frank J Dosage forms having a microreliefed surface and methods and apparatus for their production
WO2006063078A2 (en) * 2004-12-08 2006-06-15 Elan Corporation, Plc Topiramate pharmaceuticals composition
GB0427455D0 (en) * 2004-12-15 2005-01-19 Jagotec Ag Dosage forms
MX2007007836A (en) 2004-12-27 2007-08-20 Eisai R&D Man Co Ltd Method for stabilizing anti-dementia drug.
DE102005005446A1 (en) 2005-02-04 2006-08-10 Grünenthal GmbH Unbreakable dosage forms with delayed release
ITBO20050123A1 (en) * 2005-03-07 2005-06-06 Alfa Wassermann Spa Pharmaceutical formulations containing rifaximin gastroresistant
US20060204575A1 (en) * 2005-03-11 2006-09-14 Hengsheng Feng Amphetamine formulations
KR20070119658A (en) * 2005-03-29 2007-12-20 에보니크 룀 게엠베하 Multiparticulate pharmaceutical form comprising pellets with a substance having a modular effect in relation to active ingredient release
EP1863453A2 (en) * 2005-03-29 2007-12-12 Evonik Röhm GmbH Multiparticulate pharmaceutical form comprising pellets with a substance having a modular effect in relation to active ingredient release
CA2605185A1 (en) * 2005-04-06 2006-10-12 Mallinckrodt Inc. Matrix-based pulse release pharmaceutical formulation
CA2602268A1 (en) * 2005-04-12 2006-10-19 Elan Pharma International Limited Controlled release compositions comprising a cephalosporin for the treatment of a bacterial infection
US8673352B2 (en) 2005-04-15 2014-03-18 Mcneil-Ppc, Inc. Modified release dosage form
NZ562120A (en) * 2005-04-28 2010-07-30 Eisai R&D Man Co Ltd Composition comprising donepezil and memantine as antidementia agents
US20070077300A1 (en) 2005-09-30 2007-04-05 Wynn David W Oral compositions containing a salivation inducing agent
US8357394B2 (en) 2005-12-08 2013-01-22 Shionogi Inc. Compositions and methods for improved efficacy of penicillin-type antibiotics
US10064828B1 (en) * 2005-12-23 2018-09-04 Intellipharmaceutics Corp. Pulsed extended-pulsed and extended-pulsed pulsed drug delivery systems
EP1973530A2 (en) * 2005-12-30 2008-10-01 Advancis Pharmaceutical Corporation Gastric release pulse system for drug delivery
TW200808380A (en) * 2006-02-21 2008-02-16 Shinetsu Chemical Co Enteric-coated preparation for site-specific delivery of drug to site within the small intestine
CA2648280C (en) 2006-04-03 2014-03-11 Isa Odidi Controlled release delivery device comprising an organosol coat
JP5844028B2 (en) 2006-04-04 2016-01-13 ケージー アクキュイシチオン エルエルシー Oral dosage form comprising an antiplatelet agent and an acid inhibitor
US20070259930A1 (en) * 2006-04-10 2007-11-08 Knopp Neurosciences, Inc. Compositions and methods of using r(+) pramipexole
WO2007137071A2 (en) 2006-05-16 2007-11-29 Knopp Neurosciences, Inc. Compositions of r(+) and s(-) pramipexole and methods of using the same
US8518926B2 (en) 2006-04-10 2013-08-27 Knopp Neurosciences, Inc. Compositions and methods of using (R)-pramipexole
US20070238942A1 (en) * 2006-04-10 2007-10-11 Esophamet Corp. Apparatus and method for detecting gastroesophageal reflux disease (gerd)
US8524695B2 (en) 2006-12-14 2013-09-03 Knopp Neurosciences, Inc. Modified release formulations of (6R)-4,5,6,7-tetrahydro-N6-propyl-2,6-benzothiazole-diamine and methods of using the same
EP2497472A1 (en) 2006-05-16 2012-09-12 Knopp Neurosciences, Inc. Therapeutically effective amounts of R(+) and S(-) pramipexole for use in the treatment of Parkinson's disease and their pharmaceutical compositions
US8299052B2 (en) 2006-05-05 2012-10-30 Shionogi Inc. Pharmaceutical compositions and methods for improved bacterial eradication
AU2006343596A1 (en) 2006-05-12 2007-11-22 Shire Llc Controlled dose drug delivery system
US20140010860A1 (en) 2006-05-12 2014-01-09 Isa Odidi Abuse and alcohol resistant drug composition
US8846100B2 (en) * 2006-05-12 2014-09-30 Shire Llc Controlled dose drug delivery system
PE09072008A1 (en) * 2006-08-31 2008-08-22 Novartis Ag Supply system gastro-retentive oral drug extended release for valsartan
ITMI20061692A1 (en) 2006-09-05 2008-03-06 Alfa Wassermann Spa Use of polyols to obtain stable polymorphic forms of rifaximin
US8580855B2 (en) * 2006-10-20 2013-11-12 Mcneil-Ppc, Inc. Acetaminophen / ibuprofen combinations and method for their use
US8778924B2 (en) 2006-12-04 2014-07-15 Shionogi Inc. Modified release amoxicillin products
US20100104621A1 (en) * 2007-02-21 2010-04-29 Connected Health Systems, Llc Treating adhd and other diseases involving inflammation
CN101715443A (en) 2007-03-14 2010-05-26 诺普神经科学股份有限公司 synthesis of chirally purified substituted benzothiazole diamines
US20080268047A1 (en) * 2007-04-24 2008-10-30 Xavier University Of Louisiana Controlled Release Multiple Layer Coatings
US20080317678A1 (en) * 2007-06-22 2008-12-25 Szymczak Christopher E Laser Marked Dosage Forms
US20080317677A1 (en) * 2007-06-22 2008-12-25 Szymczak Christopher E Laser Marked Dosage Forms
US8478862B2 (en) * 2007-07-13 2013-07-02 Front Porch, Inc. Method and apparatus for internet traffic monitoring by third parties using monitoring implements
US7953851B2 (en) * 2007-07-13 2011-05-31 Front Porch, Inc. Method and apparatus for asymmetric internet traffic monitoring by third parties using monitoring implements
EP2044932A1 (en) * 2007-10-04 2009-04-08 Laboratorios del Dr. Esteve S.A. Mechanical protective layer for solid dosage forms
EP2044929A1 (en) * 2007-10-04 2009-04-08 Laboratorios del Dr. Esteve S.A. Oral fast distintegrating tablets
ES2633449T3 (en) * 2007-10-31 2017-09-21 Johnson & Johnson Consumer Inc. Orally disintegrable dosage form
EP2219622A1 (en) 2007-12-06 2010-08-25 Durect Corporation Methods useful for the treatment of pain, arthritic conditions, or inflammation associated with a chronic condition
EP2227226B1 (en) * 2007-12-21 2016-10-26 Johnson & Johnson Consumer Inc. Manufacture of a tablet
CA2715584A1 (en) * 2008-02-15 2009-10-08 Sun Pharma Advanced Research Company Ltd. Oral controlled release tablet
CA2721493C (en) 2008-04-18 2017-11-28 Intec Pharma Ltd. Carbidopa/levodopa gastroretentive drug delivery
WO2009158368A1 (en) * 2008-06-26 2009-12-30 Mcneil-Ppc, Inc. Coated particles containing pharmaceutically active agents
US9009838B2 (en) * 2008-07-24 2015-04-14 Front Porch, Inc. Method and apparatus for effecting an internet user's privacy directive
KR20110071064A (en) 2008-08-19 2011-06-28 크놉 뉴로사이언시스 인코포레이티드 Compositions and methods of using (r)-pramipexole
US20100260844A1 (en) 2008-11-03 2010-10-14 Scicinski Jan J Oral pharmaceutical dosage forms
KR101211338B1 (en) 2008-11-25 2012-12-11 닛산 지도우샤 가부시키가이샤 A conductive member and a polymer electrolyte fuel cell using the same
EP2378883B1 (en) * 2008-12-04 2015-12-23 Intec Pharma Ltd. Zaleplon gastroretentive drug delivery system
RU2012101792A (en) * 2009-06-19 2013-07-27 Нопп Ньюросайенсиз, Инк. Compositions and methods for the treatment of amyotrophic lateral sclerosis
EP2456424B1 (en) 2009-07-22 2013-08-28 Grünenthal GmbH Oxidation-stabilized tamper-resistant dosage form
PE10672012A1 (en) 2009-07-22 2012-09-05 Gruenenthal Chemie Form of controlled release dosage extruded by hot melt
US8313768B2 (en) 2009-09-24 2012-11-20 Mcneil-Ppc, Inc. Manufacture of tablet having immediate release region and sustained release region
US8784781B2 (en) 2009-09-24 2014-07-22 Mcneil-Ppc, Inc. Manufacture of chewing gum product with radiofrequency
GB201002612D0 (en) * 2010-02-16 2010-03-31 Jagotec Ag Improvements in or relating to organic compounds
PL2560624T3 (en) * 2010-04-23 2019-01-31 Kempharm, Inc. Therapeutic formulation for reduced drug side effects
JP5865904B2 (en) 2010-06-16 2016-02-17 タケダ ファーマシューティカルズ ユー.エス.エー. インコーポレイティド Novel modified release dosage form of xanthine oxidoreductase inhibitor or a xanthine oxidase inhibitor
US20110318411A1 (en) 2010-06-24 2011-12-29 Luber Joseph R Multi-layered orally disintegrating tablet and the manufacture thereof
KR20130097202A (en) 2010-09-02 2013-09-02 그뤼넨탈 게엠베하 Tamper resistant dosage form comprising inorganic salt
EP2688557B1 (en) * 2011-03-23 2017-08-23 Ironshore Pharmaceuticals & Development, Inc. Methods and compositions for treatment of attention deficit disorder
US8916588B2 (en) 2011-03-23 2014-12-23 Ironshore Pharmaceuticals & Development, Inc. Methods for treatment of attention deficit hyperactivity disorder
US8927010B2 (en) 2011-03-23 2015-01-06 Ironshore Pharmaceuticals & Development, Inc. Compositions for treatment of attention deficit hyperactivity disorder
US9283214B2 (en) 2011-03-23 2016-03-15 Ironshore Pharmaceuticals & Development, Inc. Compositions for treatment of attention deficit hyperactivity disorder
US9603809B2 (en) 2011-03-23 2017-03-28 Ironshore Pharmaceuticals & Development, Inc. Methods of treatment of attention deficit hyperactivity disorder
US9119809B2 (en) 2011-03-23 2015-09-01 Ironshore Pharmaceuticals & Development, Inc. Compositions for treatment of attention deficit hyperactivity disorder
US10292937B2 (en) 2011-03-23 2019-05-21 Ironshore Pharmaceuticals & Development, Inc. Methods of treatment of attention deficit hyperactivity disorder
US9498447B2 (en) 2011-03-23 2016-11-22 Ironshore Pharmaceuticals & Development, Inc. Compositions for treatment of attention deficit hyperactivity disorder
EP2726066A4 (en) 2011-06-28 2015-06-03 Neos Therapeutics Lp Dosage forms for oral administration and methods of treatment using the same
HUE034711T2 (en) 2011-07-29 2018-02-28 Gruenenthal Gmbh Tamper-resistant tablet providing immediate drug release
EP2768481A4 (en) * 2011-10-21 2015-07-08 Subhash Desai Compositions for reduction of side effects
CA2758556A1 (en) * 2011-11-17 2013-05-17 Pharmascience Inc. Pharmaceutical composition of amphetamine mixed salts
US9512096B2 (en) 2011-12-22 2016-12-06 Knopp Biosciences, LLP Synthesis of amine substituted 4,5,6,7-tetrahydrobenzothiazole compounds
US9511028B2 (en) 2012-05-01 2016-12-06 Johnson & Johnson Consumer Inc. Orally disintegrating tablet
US9445971B2 (en) 2012-05-01 2016-09-20 Johnson & Johnson Consumer Inc. Method of manufacturing solid dosage form
US9233491B2 (en) 2012-05-01 2016-01-12 Johnson & Johnson Consumer Inc. Machine for production of solid dosage forms
US10064945B2 (en) 2012-05-11 2018-09-04 Gruenenthal Gmbh Thermoformed, tamper-resistant pharmaceutical dosage form containing zinc
US9662313B2 (en) 2013-02-28 2017-05-30 Knopp Biosciences Llc Compositions and methods for treating amyotrophic lateral sclerosis in responders
US8652527B1 (en) 2013-03-13 2014-02-18 Upsher-Smith Laboratories, Inc Extended-release topiramate capsules
US9101545B2 (en) 2013-03-15 2015-08-11 Upsher-Smith Laboratories, Inc. Extended-release topiramate capsules
US9572885B2 (en) 2013-03-15 2017-02-21 Durect Corporation Compositions with a rheological modifier to reduce dissolution variability
JP6445537B2 (en) 2013-05-29 2018-12-26 グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング Modified anti containing one or more particles (tamper-resistant) dosage forms
US9468630B2 (en) 2013-07-12 2016-10-18 Knopp Biosciences Llc Compositions and methods for treating conditions related to increased eosinophils
AU2014306683B2 (en) 2013-08-13 2017-10-12 Knopp Biosciences Llc Compositions and methods for treating plasma cell disorders and B-cell prolymphocytic disorders
WO2015023790A1 (en) 2013-08-13 2015-02-19 Knopp Biosciences Llc Compositions and methods for treating chronic urticaria
WO2015105992A1 (en) 2014-01-10 2015-07-16 Mcneil-Ppc, Inc. Process for making tablet using radiofrequency and lossy coated particles
JP2017518980A (en) 2014-05-12 2017-07-13 グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング Containing tapentadol, modified prevent immediate release capsule formulation
MX2016015417A (en) 2014-05-26 2017-02-22 Grünenthal GmbH Multiparticles safeguarded against ethanolic dose-dumping.
AU2016225052A1 (en) * 2015-02-27 2017-09-21 Cingulate Therapeutics LLC Tripulse release stimulant formulations
KR20170139158A (en) 2015-04-24 2017-12-18 그뤼넨탈 게엠베하 Immediately released and prevent the tamper-resistant dosage form extraction solvent
US10142086B2 (en) 2015-06-11 2018-11-27 At&T Intellectual Property I, L.P. Repeater and methods for use therewith
US20170296476A1 (en) 2016-04-15 2017-10-19 Grünenthal GmbH Modified release abuse deterrent dosage forms
WO2019073028A1 (en) 2017-10-13 2019-04-18 Grünenthal GmbH Modified release abuse deterrent dosage forms

Citations (58)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2099402A (en) 1934-01-17 1937-11-16 Pratt Food Company Pill or tablet
US2738303A (en) 1952-07-18 1956-03-13 Smith Kline French Lab Sympathomimetic preparation
US2881113A (en) * 1957-01-29 1959-04-07 Ortho Pharma Corp Therapeutically active compositions containing amphetamines
US3048526A (en) 1958-08-04 1962-08-07 Wander Company Medicinal tablet
US3066075A (en) * 1960-07-25 1962-11-27 G W Carnrick Co Compositions comprising amphetamine and carboxymethyl cellulose in chemically combined form
US3365365A (en) 1965-08-09 1968-01-23 Hoffmann La Roche Repeat action pharmaceutical compositions in the form of discrete beadlets
US3979349A (en) 1973-05-07 1976-09-07 Rohm Gmbh Dispersions of water-soluble polymers and methods for making and using the same
US4049791A (en) 1974-06-21 1977-09-20 Delco Chemical Company, Inc. Prolonged acting appetite suppressant and anti-obesity compositions containing amphetamine adipate, dextroamphetamine adipate, amphetamine sulfate and dextroamphetamine sulfate as the active agents
JPS5982311A (en) 1982-11-04 1984-05-12 Shionogi & Co Ltd Sustained release preparation of cephalexin
WO1987000044A1 (en) 1985-07-02 1987-01-15 The Upjohn Company Therapeutic formulations with bimodal release characteristics
US4723958A (en) 1986-05-23 1988-02-09 Merck & Co., Inc. Pulsatile drug delivery system
US4728512A (en) 1985-05-06 1988-03-01 American Home Products Corporation Formulations providing three distinct releases
US4794001A (en) 1986-03-04 1988-12-27 American Home Products Corporation Formulations providing three distinct releases
US4871549A (en) 1985-07-19 1989-10-03 Fujisawa Pharmaceutical Co., Ltd. Time-controlled explosion systems and processes for preparing the same
US4891230A (en) 1983-12-22 1990-01-02 Elan Corporation Plc Diltiazem formulation
US4894240A (en) 1983-12-22 1990-01-16 Elan Corporation Plc Controlled absorption diltiazem formulation for once-daily administration
US4902516A (en) 1987-04-10 1990-02-20 Chemie Holding Aktiengesellschaft Binder-free granules with delayed release of the active compound
US4917899A (en) 1983-12-22 1990-04-17 Elan Corporation Plc Controlled absorption diltiazem formulation
WO1990009168A1 (en) 1989-02-16 1990-08-23 National Research Development Corporation Dispensing device
US5002776A (en) 1983-12-22 1991-03-26 Elan Corporation, Plc Controlled absorption diltiazem formulations
US5011694A (en) 1988-08-11 1991-04-30 Rohm Gmbh Pharmaceutical dosage unit forms with delayed release
US5011692A (en) 1985-12-28 1991-04-30 Sumitomo Pharmaceuticals Company, Limited Sustained pulsewise release pharmaceutical preparation
JPH03148215A (en) 1989-11-01 1991-06-25 Nippon Shinyaku Co Ltd Laminated formulation
US5051262A (en) 1979-12-07 1991-09-24 Elan Corp., P.L.C. Processes for the preparation of delayed action and programmed release pharmaceutical forms and medicaments obtained thereby
US5093200A (en) 1985-10-23 1992-03-03 Eisai Co., Ltd. Multilayer sustained release granule
US5137733A (en) 1990-06-28 1992-08-11 Tanabe Seiyaku Co., Ltd. Controlled release pharmaceutical preparation
US5156850A (en) 1990-08-31 1992-10-20 Alza Corporation Dosage form for time-varying patterns of drug delivery
US5202159A (en) 1990-12-27 1993-04-13 Standard Chemical & Pharmaceutical Corp., Ltd. Preparation method of microdispersed tablet formulation of spray-dried sodium diclofenac enteric-coated microcapsules
US5226902A (en) 1991-07-30 1993-07-13 University Of Utah Pulsatile drug delivery device using stimuli sensitive hydrogel
US5229131A (en) 1990-02-05 1993-07-20 University Of Michigan Pulsatile drug delivery system
US5260069A (en) 1992-11-27 1993-11-09 Anda Sr Pharmaceuticals Inc. Pulsatile particles drug delivery system
US5260068A (en) 1992-05-04 1993-11-09 Anda Sr Pharmaceuticals Inc. Multiparticulate pulsatile drug delivery system
US5275819A (en) 1989-02-06 1994-01-04 Amer Particle Technologies Inc. Drug loaded pollen grains with an outer coating for pulsed delivery
US5308348A (en) 1992-02-18 1994-05-03 Alza Corporation Delivery devices with pulsatile effect
US5328697A (en) * 1992-02-10 1994-07-12 Mallinckrodt Veterinary, Inc. Compositions and processes for the sustained release of drugs
US5364620A (en) 1983-12-22 1994-11-15 Elan Corporation, Plc Controlled absorption diltiazem formulation for once daily administration
US5378474A (en) 1989-01-06 1995-01-03 F. H. Faulding & Co. Limited Sustained release pharmaceutical composition
EP0640337A2 (en) 1993-08-25 1995-03-01 Ss Pharmaceutical Co., Ltd. Controlled release-initiation and controlled release-rate pharmaceutical composition
US5395628A (en) 1989-12-28 1995-03-07 Tanabe Seiyaku Co., Ltd. Controlled release succinic acid microcapsules coated with aqueous acrylics
US5407686A (en) 1991-11-27 1995-04-18 Sidmak Laboratories, Inc. Sustained release composition for oral administration of active ingredient
US5422121A (en) 1990-11-14 1995-06-06 Rohm Gmbh Oral dosage unit form
US5474786A (en) 1994-03-23 1995-12-12 Ortho Pharmaceutical Corporation Multilayered controlled release pharmaceutical dosage form
WO1997003673A1 (en) 1995-07-14 1997-02-06 Medeva Europe Limited Sustained-release formulation of d-threo-methylphenidate
JPH09249557A (en) 1996-03-14 1997-09-22 Shionogi & Co Ltd Sustained release preparation of slightly water-soluble medicine
JPH09267035A (en) 1996-01-30 1997-10-14 Kanegafuchi Chem Ind Co Ltd Production of nuclear particle
JPH1081634A (en) 1996-07-18 1998-03-31 Taisho Pharmaceut Co Ltd Base controlled in dissolution time
WO1998014168A2 (en) 1996-09-30 1998-04-09 Alza Corporation Dosage form providing a sustained and ascending drug release
US5773031A (en) * 1996-02-27 1998-06-30 L. Perrigo Company Acetaminophen sustained-release formulation
US5837284A (en) * 1995-12-04 1998-11-17 Mehta; Atul M. Delivery of multiple doses of medications
US5840329A (en) 1997-05-15 1998-11-24 Bioadvances Llc Pulsatile drug delivery system
US6005027A (en) * 1995-08-16 1999-12-21 Witco Corporation Stable silane compositions on silica carrier
WO2000025752A1 (en) 1998-11-02 2000-05-11 Church, Marla, J. Multiparticulate modified release composition
WO2000035450A1 (en) 1998-12-17 2000-06-22 Euro-Celtique S.A. Controlled/modified release oral methylphenidate formulations
US6475493B1 (en) 1999-09-02 2002-11-05 Norstrum Pharmaceuticals, Inc. Controlled release pellet formulation
US6605300B1 (en) * 1998-10-21 2003-08-12 Shire Laboratories, Inc. Oral pulsed dose drug delivery system
US20040059002A1 (en) 2002-09-24 2004-03-25 Shire Laboratories, Inc. Sustained release delivery of amphetamine salts
US6749867B2 (en) 2000-11-29 2004-06-15 Joseph R. Robinson Delivery system for omeprazole and its salts
US6764696B2 (en) 1998-04-29 2004-07-20 Cima Labs Inc. Effervescent drug delivery system for oral administration

Family Cites Families (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2993836A (en) * 1958-02-20 1961-07-25 Dow Chemical Co Sustained release tablets
NL297631A (en) * 1963-06-03
ZA8205384B (en) 1981-07-31 1983-05-25 Tillott J B Ltd Orally administrable pharmaceutical compositions
US4765989A (en) 1983-05-11 1988-08-23 Alza Corporation Osmotic device for administering certain drugs
JPH05502465A (en) 1989-08-28 1993-04-28
US5232705A (en) * 1990-08-31 1993-08-03 Alza Corporation Dosage form for time-varying patterns of drug delivery
NZ241413A (en) * 1991-01-30 1994-12-22 Alza Corp Fluid-imbibing dispensing device
DE69331839T2 (en) * 1992-01-29 2002-12-12 Takeda Chemical Industries Ltd Rapidly dissolving tablet, and their preparation
US5322697A (en) * 1992-05-28 1994-06-21 Meyer James H Composition and method for inducing satiety
NZ253999A (en) * 1992-08-05 1996-07-26 Faulding F H & Co Ltd Pelletised substained release medicament
US6103262A (en) 1994-01-27 2000-08-15 G. D. Searle & Company Modified-release metronidazole compositions and methods for making and using same
US5411745A (en) 1994-05-25 1995-05-02 Euro-Celtique, S.A. Powder-layered morphine sulfate formulations
US5582855A (en) 1994-07-01 1996-12-10 Fuisz Technologies Ltd. Flash flow formed solloid delivery systems
FR2723536A1 (en) * 1994-08-11 1996-02-16 Seth Pawan Composition enabling selective release of an active ingredient
US5733575A (en) 1994-10-07 1998-03-31 Bpsi Holdings, Inc. Enteric film coating compositions, method of coating therewith, and coated forms
US5731314A (en) * 1995-01-06 1998-03-24 Bencherif; Merouane Pharamceutical compositions for prevention and treatment of tourette's syndrome
US5908850A (en) * 1995-12-04 1999-06-01 Celgene Corporation Method of treating attention deficit disorders with d-threo methylphenidate
US5922736A (en) * 1995-12-04 1999-07-13 Celegene Corporation Chronic, bolus administration of D-threo methylphenidate
US5846568A (en) * 1996-09-19 1998-12-08 Xyrofin Oy Directly compressible lactitol and method
HRP970493A2 (en) * 1996-09-23 1998-08-31 Wienman E. Phlips Oral delayed immediate release medical formulation and method for preparing the same
US5891474A (en) * 1997-01-29 1999-04-06 Poli Industria Chimica, S.P.A. Time-specific controlled release dosage formulations and method of preparing same
US5885616A (en) 1997-08-18 1999-03-23 Impax Pharmaceuticals, Inc. Sustained release drug delivery system suitable for oral administration
US5945123A (en) * 1998-04-02 1999-08-31 K-V Pharmaceutical Company Maximizing effectiveness of substances used to improve health and well being
US6340476B1 (en) * 1999-04-06 2002-01-22 Armaquest, Inc. Pharmaceutical dosage form for pulsatile delivery of methylphenidate

Patent Citations (62)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2099402A (en) 1934-01-17 1937-11-16 Pratt Food Company Pill or tablet
US2738303A (en) 1952-07-18 1956-03-13 Smith Kline French Lab Sympathomimetic preparation
US2881113A (en) * 1957-01-29 1959-04-07 Ortho Pharma Corp Therapeutically active compositions containing amphetamines
US3048526A (en) 1958-08-04 1962-08-07 Wander Company Medicinal tablet
US3066075A (en) * 1960-07-25 1962-11-27 G W Carnrick Co Compositions comprising amphetamine and carboxymethyl cellulose in chemically combined form
US3365365A (en) 1965-08-09 1968-01-23 Hoffmann La Roche Repeat action pharmaceutical compositions in the form of discrete beadlets
US3979349A (en) 1973-05-07 1976-09-07 Rohm Gmbh Dispersions of water-soluble polymers and methods for making and using the same
US4049791A (en) 1974-06-21 1977-09-20 Delco Chemical Company, Inc. Prolonged acting appetite suppressant and anti-obesity compositions containing amphetamine adipate, dextroamphetamine adipate, amphetamine sulfate and dextroamphetamine sulfate as the active agents
US5051262A (en) 1979-12-07 1991-09-24 Elan Corp., P.L.C. Processes for the preparation of delayed action and programmed release pharmaceutical forms and medicaments obtained thereby
JPS5982311A (en) 1982-11-04 1984-05-12 Shionogi & Co Ltd Sustained release preparation of cephalexin
US5364620A (en) 1983-12-22 1994-11-15 Elan Corporation, Plc Controlled absorption diltiazem formulation for once daily administration
US5002776A (en) 1983-12-22 1991-03-26 Elan Corporation, Plc Controlled absorption diltiazem formulations
US4917899A (en) 1983-12-22 1990-04-17 Elan Corporation Plc Controlled absorption diltiazem formulation
US4894240A (en) 1983-12-22 1990-01-16 Elan Corporation Plc Controlled absorption diltiazem formulation for once-daily administration
US4891230A (en) 1983-12-22 1990-01-02 Elan Corporation Plc Diltiazem formulation
US5616345A (en) 1983-12-22 1997-04-01 Elan Corporation Plc Controlled absorption diltiazen formulation for once-daily administration
US4728512A (en) 1985-05-06 1988-03-01 American Home Products Corporation Formulations providing three distinct releases
WO1987000044A1 (en) 1985-07-02 1987-01-15 The Upjohn Company Therapeutic formulations with bimodal release characteristics
US4871549A (en) 1985-07-19 1989-10-03 Fujisawa Pharmaceutical Co., Ltd. Time-controlled explosion systems and processes for preparing the same
US5093200A (en) 1985-10-23 1992-03-03 Eisai Co., Ltd. Multilayer sustained release granule
US5011692A (en) 1985-12-28 1991-04-30 Sumitomo Pharmaceuticals Company, Limited Sustained pulsewise release pharmaceutical preparation
US4794001A (en) 1986-03-04 1988-12-27 American Home Products Corporation Formulations providing three distinct releases
US4723958A (en) 1986-05-23 1988-02-09 Merck & Co., Inc. Pulsatile drug delivery system
US4902516A (en) 1987-04-10 1990-02-20 Chemie Holding Aktiengesellschaft Binder-free granules with delayed release of the active compound
US5011694A (en) 1988-08-11 1991-04-30 Rohm Gmbh Pharmaceutical dosage unit forms with delayed release
US5378474A (en) 1989-01-06 1995-01-03 F. H. Faulding & Co. Limited Sustained release pharmaceutical composition
US5275819A (en) 1989-02-06 1994-01-04 Amer Particle Technologies Inc. Drug loaded pollen grains with an outer coating for pulsed delivery
WO1990009168A1 (en) 1989-02-16 1990-08-23 National Research Development Corporation Dispensing device
JPH03148215A (en) 1989-11-01 1991-06-25 Nippon Shinyaku Co Ltd Laminated formulation
US5395628A (en) 1989-12-28 1995-03-07 Tanabe Seiyaku Co., Ltd. Controlled release succinic acid microcapsules coated with aqueous acrylics
US5229131A (en) 1990-02-05 1993-07-20 University Of Michigan Pulsatile drug delivery system
US5137733A (en) 1990-06-28 1992-08-11 Tanabe Seiyaku Co., Ltd. Controlled release pharmaceutical preparation
US5156850A (en) 1990-08-31 1992-10-20 Alza Corporation Dosage form for time-varying patterns of drug delivery
US5422121A (en) 1990-11-14 1995-06-06 Rohm Gmbh Oral dosage unit form
US5202159A (en) 1990-12-27 1993-04-13 Standard Chemical & Pharmaceutical Corp., Ltd. Preparation method of microdispersed tablet formulation of spray-dried sodium diclofenac enteric-coated microcapsules
US5226902A (en) 1991-07-30 1993-07-13 University Of Utah Pulsatile drug delivery device using stimuli sensitive hydrogel
US5407686A (en) 1991-11-27 1995-04-18 Sidmak Laboratories, Inc. Sustained release composition for oral administration of active ingredient
US5328697A (en) * 1992-02-10 1994-07-12 Mallinckrodt Veterinary, Inc. Compositions and processes for the sustained release of drugs
US5308348A (en) 1992-02-18 1994-05-03 Alza Corporation Delivery devices with pulsatile effect
US5260068A (en) 1992-05-04 1993-11-09 Anda Sr Pharmaceuticals Inc. Multiparticulate pulsatile drug delivery system
US5260069A (en) 1992-11-27 1993-11-09 Anda Sr Pharmaceuticals Inc. Pulsatile particles drug delivery system
JPH0761922A (en) 1993-08-25 1995-03-07 Ss Pharmaceut Co Ltd Release start controlling type pharmaceutical preparation
EP0640337A2 (en) 1993-08-25 1995-03-01 Ss Pharmaceutical Co., Ltd. Controlled release-initiation and controlled release-rate pharmaceutical composition
US5496561A (en) 1993-08-25 1996-03-05 Ss Pharmaceutical Co., Ltd. Controlled release-initiation and controlled release-rate pharmaceutical composition
US5474786A (en) 1994-03-23 1995-12-12 Ortho Pharmaceutical Corporation Multilayered controlled release pharmaceutical dosage form
WO1997003673A1 (en) 1995-07-14 1997-02-06 Medeva Europe Limited Sustained-release formulation of d-threo-methylphenidate
US6005027A (en) * 1995-08-16 1999-12-21 Witco Corporation Stable silane compositions on silica carrier
US5837284A (en) * 1995-12-04 1998-11-17 Mehta; Atul M. Delivery of multiple doses of medications
JPH09267035A (en) 1996-01-30 1997-10-14 Kanegafuchi Chem Ind Co Ltd Production of nuclear particle
US5773031A (en) * 1996-02-27 1998-06-30 L. Perrigo Company Acetaminophen sustained-release formulation
JPH09249557A (en) 1996-03-14 1997-09-22 Shionogi & Co Ltd Sustained release preparation of slightly water-soluble medicine
JPH1081634A (en) 1996-07-18 1998-03-31 Taisho Pharmaceut Co Ltd Base controlled in dissolution time
WO1998014168A2 (en) 1996-09-30 1998-04-09 Alza Corporation Dosage form providing a sustained and ascending drug release
US5840329A (en) 1997-05-15 1998-11-24 Bioadvances Llc Pulsatile drug delivery system
WO1999003471A1 (en) 1997-07-14 1999-01-28 Mehta, Atul, M. Improved delivery of multiple doses of medications
US6764696B2 (en) 1998-04-29 2004-07-20 Cima Labs Inc. Effervescent drug delivery system for oral administration
US6605300B1 (en) * 1998-10-21 2003-08-12 Shire Laboratories, Inc. Oral pulsed dose drug delivery system
WO2000025752A1 (en) 1998-11-02 2000-05-11 Church, Marla, J. Multiparticulate modified release composition
WO2000035450A1 (en) 1998-12-17 2000-06-22 Euro-Celtique S.A. Controlled/modified release oral methylphenidate formulations
US6475493B1 (en) 1999-09-02 2002-11-05 Norstrum Pharmaceuticals, Inc. Controlled release pellet formulation
US6749867B2 (en) 2000-11-29 2004-06-15 Joseph R. Robinson Delivery system for omeprazole and its salts
US20040059002A1 (en) 2002-09-24 2004-03-25 Shire Laboratories, Inc. Sustained release delivery of amphetamine salts

Non-Patent Citations (156)

* Cited by examiner, † Cited by third party
Title
Adderall XR Package Inset, Sep. (2004).
Agyilirah GA and Bauker SB, Polymers for Enteric Coating Applications, Polymers for Controlled Drug Delivery (Peter J. Tarcha ed. 1991) 39-66.
American Chemical Society, Polymer Preprints, pp. 633-634, vol. 34, No. 1, Mar. 1993.
Angrist et al., Early Pharmacokinetics and Clinical Effects of Oral D-Amphetamine in Normal Subjects, Biol. Psychiatry 1987, 22: 1357-1368.
Ansel, et al., Rate Controlled Dosage Forms and Drug Delivery Systems, Pharmaceutical Dosage Forms and Drug Delivery Systems, 6th Ed. (1995), 213-222.
Answer and Counterclaims in Shire Laboratories, Inc. v. Andrx, LLC, in the United States District Court for the Southern District of Florida, Miami Division, Case No. 07-22201-CIV-Cooke/Brown, Aug. 31, 2007.
Answering Expert Report of Dr. Alexander Klibanov, Apr. 25, 2005.
Answering Expert Report of Robert Langer, Apr. 25, 2005.
Barr Laboratories Inc.'s Objections and Responses to Shire Laboratories Inc.'s Second Set of Interrogatories (Nos. 8-11), dated Feb. 18, 2004.
Barr Laboratories' Memorandum In Support of its Motion to Amend its Pleadings and exhibits thereto, dated Sep. 10, 2004.
Barr Laboratories' Memorandum in Support of its Motion to Compel Production, dated Sep. 13, 2004.
Barr Laboratories' Objections and Responses to Plaintiff Shire Laboratories Inc.'s Fifth Set of Interrogatories (No. 17), dated Sep. 3, 2004.
Barr Laboratories' Objections and Responses to Plaintoff Shire Laboratories Inc.'s Fourth Set of Interrogatories (Nos. 15-16), dated Jul. 9, 2004.
Barr Laboratories' Supplemetal Objections and Responses to Plaintiff Shire Laboratories Inc.'s Third Set of Interrogatories (Nos. 12-14 Redacted), dated Aug. 27, 2004.
Bauer, et al., Cellulose Acetate Phthalate (CAP) and Trimellitate (CAT), Coated Pharmaceutical Dosage Forms (1998), 102-104.
Bodmeier et al., The Influence of Buffer Species and Strength on Diltiazem HCl Release from Beads Coated with the Aqueous Catinoc Polymer Dispensions, Eudragit RS, RL 30D, Pharmaceutical Research vol. 13, No. 1, 1996, 52-56.
Brauer et al., Acute Tolerance to Subjective but not Cardiovascular Effects of d-Amphetamine in normal, Healthy Men, Journal of Clinical Psychopharmacology, 1996; 16(1):73-76.
Brown et al., Behavior and Motor Activity Response in Hyperactive Children and Plasma Amphetamine Levels Following a Sustained Release Preparation, Journal of the American Academy of Child Psychiatry, 19:225-239, 1980.
Brown et al., Plasma Levels of d-Amphetamine in Hyperactive Children, Psychopharmacology 62, 133-140, 1979.
Burns et al., A study of Enteric-coated Liquid-filled Hard Gelatin Capsules with Biphasic Release Characteristics, International Journal of Pharmaceutics 110 (1994) 291-296.
Burnside Deposition Transcript, Feb. 2, 2005.
Burnside Deposition Transcript, Feb. 3, 2005.
C. Lin et al., Biovailability of d-pseudoephedrine and Azatadine from a Repeat Action Tablet Formulation, J Int Med Res (1982), 122-125.
C. Lin et al., Comparative Biovailability of d-pseudoephedrine from a Conventional d-pseudoephedrine Sulfate Tablet and from a Repeat Action Tablet, J Int Med Res (1982) 10, 126-128.
Chan, Materials Used for Effective Sustained-Release Products, Proceedings of the International Symposium held on 29th to 31st of Jan. 1987 (The Bombay College of Pharmacy 1988), 69-84.
Chan, New Polymers for Controlled Release Products, Controlled Release Dosage Forms Proceedings of the International Symposium held on 29th to 31st of Jan. 1987 (The Bombay College of Pharmacy 1988) 59-67.
Chang Deposition Transcript, Jan. 20, 2005.
Chang Deposition Transcript, Sep. 8, 2004.
Chang et al., Preparation and Evaluation of Shellac Pseudolatex as an Aqueous Enteric Coating Systems for Pellets, International Journal of Pharmaceuticals, 60 (1990) 171-173, 1990.
Charles S.L. Chlao amd Joseph R. Robinson, Sustained-Release Drug Delivery Systems, Remington: The Science and Practice of Pharmacy, Tenth Edition (1995) 1660-1675.
Cody et al., Amphetamine Enantiomer Excretion Profile Following Administration of Adderall, Journal of Analytical Toxicology, vol. 2, Oct. 2003, 485-492.
Complaint for Declaratory Judgment, Impax Laboratories Inc. v. Shire International Laboratories, Inc. (Civ. Action No. 05772) and Exhibits attached thereto, dated Nov. 9, 2005.
Conte, et al., "Press-coated tablets for time-programmed release of drugs," Biomaterials, 14(13):1017-1023 (1993).
Couch Deposition Transcript, Sep. 8, 2004.
Daynes, Treatment of Noctural Enuresis with Enteric-Coated Amphetamine, The Practitioner, No. 1037, vol. 173, Nov. 1954.
Defendant Sandoz, Inc.'s Answers and Objections to Plaintiff Shire LLC's Interrogatories (No. 1-9), in the United States District Court for the District of Colorado, Case No. 07-CV-001197-EWN-CBS, Jun. 18, 2007.
Defendant Sandoz, Inc.'s Answers and Objections to Plaintiff Shire LLC's Second Set of Interrogatories (No. 10-19), in the United States District Court for the District of Colorado, Case No. 07-CV-001197-EWN-CBS, Nov. 20, 2007.
Defendant Sandoz, Inc.'s Answers and Objections to Plaintiff Shire LLC's Second Set of Interrogatories (No. 20-25) and Supplement to Answers to Interrogatories 8 and 9, in the United States District Court for the District of Colorado, Case No. 07-CV-001197-EWN-CBS, Dec. 10, 2007.
Deposition transcript of Honorable Gerald J. Mossinghoff and exhibits thereto, dated Jun. 8, 2005.
Edward Stempel, Prolonged Drug Action, HUSA's Pharmaceutical Dispensing, Sixth Edition, 1966, 464, 481-485.
Expert Report of Arthur J. Steiner in Shire LLC v. Colony Pharmaceuticals, Inc., in the United States District Court for the District of Maryland, case No. 1:07-cv-00718, Dec. 20, 2007.
Expert Report of Dr. Joseph R. Robinson and exhibits thereto, Feb. 28, 2005.
Expert Report of the Honorable Gerald J. Mossinghoff and exhibits thereto, Mar. 16, 2005.
Fiske Deposition Transcript, Sep. 17, 2004.
Freedom of Information Request Results for—Dexadrine (SmithKline Beecham): May 20, 1976 Disclosable Approval Information.
Fukumori, Coating of Multiparticulates Using Polymeric Dispersions, Multiparticulate Oral Drug Delivery (Swarbrick and Selassie eds. 1994), 79-110.
Garnett et al., Pharmacokinitic Evaluation of Twice-Daily Extended-Release Carbamazepine (CBZ) and Four-Times-Daily Immediate-Release CBZ in Patients with Epilepsy, Epilepsia 39(3):274-279, 1998.
Gazzaniga, et al., "Oral Chronotopic Drug Delivery Systems: Achievement of Time and/or Site Specificity," Eur. J. Pharm. Biopharma 40(3):246-250 (1994).
Gazzaniga, et al., "Time-dependent oral delivery systems for colon targeting," S.T.P. Pharma Sciences, 5(1):83-88 (1995).
Ghebre-Sellassie et ., "Evaluation of acrylic-based modified-release film coatings," International Journal of Pharmaceutics, 1987;37:211-218.
Goodhart et al., An Evaluation of Aqueous Film-Forming Dispersions for Controlled Release, Pharmaceutical Technology, Apr. 1984.
Greenhill et al., A Pharmacokinetic/Pharmacodynamic Study Comparing a Single Morning Dose of Adderall to Twice-Daily Dosing in Children with ADHD. J. Am. Acad. Adolesc. Psychiatry, 42:10, Oct. 2003.
Guidance for Industry: Extended Release Oral Dosage Forms: Development, Evaluation, and Application of In Vitro/In Vivo Correlations (1997).
Guidance for Industry: Food-Effext Bioavailability and Fed Bioequivalence Studies (2002).
Guidance for Industry: SUPAC-MR: Modified Release Solid Oral Dosage Forms (1997).
Guo Deposition Transcript, Jan. 24, 2005.
Guo Deposition Transcript, Jul. 26, 2004.
Hall HS and Pondell RE, Controlled Release Technologies: Method, Theory, and Applications, pp. 133-154 (Agis F. Kydonieus ed. 1980).
Handbook of Pharmaceutical Excipients: Ethylcellulose, Polymethacrylates, (4th ed. (2003), 237-240, 462-468.
Handbook of Pharmaceutical Excipients: Plymethacrylates, (2nd ed. 1994), 361-366.
Hans-Martin Klein & Rolf W. Gunther, Double Contrast Small Bowell Follow-Through with an Acid-Resistant Effervescent Agent, Investigative Radiology vol. 28, Jul. 1993.
Harrington Deposition Transcript, Jul. 27, 2005.
Harris et al., Aqueous Polymeric Coating for Modified-Release Pellets, Aqueous Polymeric Coating for Pharmaceutical Dosage Forms (McGinity ed., 1989).
Hawley's Condensed Chemical Dictionary 13th Ed. 1997, 584, 981.
Holt, Bioequivalence Studies of Ketoprofen: Product formulation, Pharmacokinetics, Deconvolution, and In Vitro-In Vivo correlations, Thesis submitted to Oregon State University, Aug. (1997).
Husson et al., Influence of Size Polydispersity on Drug Release from Coated Pellets, International Journal of Pharmaceutics, 86 (1992) 113-121, 1992.
Impax Laboratories Inc.'s First Amended Answer and Affirmative Defenses, dated May 2, 2005.
Impax Laboratories, Inc.'s First Supplemental Responses to Shire Laboratories Inc.'s First Set of Interrogatories (Nos. 11-12).
Impax Laboratories, Inc.'s Memorandum in Support of the Motion to Amend its Answer dated Feb. 25, 2005 and exhibits thereto.
Impax Laboratories, Inc.'s Reply Memorandum in Support of the Motion to Amend its Answer dated Mar. 18, 2005 and exhibit thereto.
Interview Summary U.S. Appl. No. 11/091,010 filed date Dec. 22, 2008.
Ishibashi et al., Design and Evaluatin of a New Capsule-type Dosage Form for Colon-Targeted Delivery of Drugs, International Journal of Pharmaceutics 168, (1998) 31-40, 1998.
J. Sjogren, Controlled release oral formulation technology, Rate Control in Drug Therapy, (1985) 38-47.
Jarowski, The Pharmaceutical Pilot Plant, Pharmaceutical Dosage Forms: Tablets, vol. 3, 2nd Ed. (1990), 303-367.
Judgment and Order of Permanent Injunction in Shire LLC v. Teva Pharmaceutical Industries Ltd. in the United States District Court for the Eastern District of Pennsylvania, Civil Action No. 06-952-SD, Mar. 6, 2008.
Judgment and Order of Permanent Injuunction in Shire Laboratories, Inc. v. Andrx Pharmaceuticals, LLC, in the United States District Court for the Southern District of Florida, Miami Division, Case No. 07-22201-CIV-Cooke/Brown, Nov. 19, 2007.
Kao et al., Lag Time Method to Delay Drug Release to Various Sites in the Gastrointestinal Tract, Journal of Controlled Release 44(1997) 263-270.
Kennerly S. Patrick & John S. Markowitz, Pharmacology of Methylphenidate, Amphetamine Enantiomers and Pemoline in Attention-Deficit Hyperactivity Disorder, Human Psychopharmacology, vol. 12, 527-546 (1997).
Kiriyama et al., The Bioavailability of Oral Dosage Forms of a New HIV-1 Protease Inhibitor, KNI-272, in Beagle Dogs, Biopharmaceutics & Drug Disposition, vol. 17 125-234 (1996).
Klaus Lehmann, Coating of Multiparticulates Using Polymeric Solutions, Multiparticulate Oral Drug Delivery (Swarbrick and Sellassie ed., 1994).
Krowczynski & Brozyna, Extended-Release Dosage Forms, pp. 123-131 (1987).
Leon Lachman, Herbert A. Lieberman, Joseph L. Kanig, The Theory and Practice of Industrial Pharmacy, Second Edition (1976) 371-373.
Leopold & Eikeler, Eudragit E as Coating Material for the pH-Controlled Drug Release in the Topical Treatment of Inflammatory Bowel Disease (IBD), Journal of Drug Targeting, 1998, vol. 6, No. 2, pp. 85-94.
Lin & Cheng, In-vitro Dissolution Behaviour of Spansule-type Micropellets Prpared by Pan Coating Method, Pharm. Ind. 51 No. 5 (1989).
Liu et al., Comparative Release of Phenylprepanolamine ECl from Long-Acting Appetite Suppressant Product: Acutrim vs. Dexatrim, Drug Development and Industrial Pharmacy, 10(10), 1639-1661 (1984).
Marcotte et al., Kinetics of Protein Diffusion from a Poly(D,L-Lactide) Reservoir System, Journal of Pharmaceutical Sciences vol. 79, No. 5, May 1990.
Mathir et al., In vitro characterization of a controlled-release chlorpheniramine maleate delivery system prepared by the air-suspension technique, J. Microencapsulation, vol. 14, No. 6,743-751 (1997).
McGough et al., Pharmacokinetics of SL1381 (Adderall XR), an Extended-Release Formulation of Adderall, Journal of the American Academy of Child & Adolescent Psychiatry, vol. 42, No. 6, Jun. 2003.
McGraw-Hill Dictionary of Scientific and Technical Terms, 5th Ed. (1994), 97, 972.
McGuiness Deposition Transcript, Aug. 6, 2004.
Mehta et al., Evaluation of Fluid-bed Processes for Enteric Coating Systems, Pharmaceutical Technology, Apr. 1986.
Moller, Dissolution Testing of Delayed Release Preparations, Proceedings of the International Symposium held on 29th to 31st of Jan. 1987 (The Bombay College of Pharmacy 1988), 85-11.
Notice of Allowance in U.S. Appl. No. 11/091,011 dated Jul. 20, 2007.
Notice of Allowance U.S. Appl. No. 11/091,010 filed dated Dec. 22, 2008.
Opening Expert Report of Dr. Michael Mayersohn and exhibits thereto, Mar. 12, 2005.
Opening Expert Report of Dr. Walter Chambliss and exhibits thereto, Mar. 15, 2005.
Order and Memorandum Denying Colony's Motion for Partial Summary Judgment of Noninfringement of the '819 and '300 Patents in Shire LLC v. Colony Pharmaceuticals, Inc., in the United States District Court for the District of Maryland, Case No. CCB-07-718, Jan. 2, 2008.
Ozturk et al., "Kinetics of Release from Enteric-Coated Tablets," Pharmacutical Research 1988;5:550-565.
PDR Drug Information for Ritalin LA Capsules, Apr. (2004).
Pelham et al., A Comparison of Morning-Only and Morning/Late Afternoon Adderall to Morning-Only, Twice-Daily, and Three Times-Daily Methylphenidate in Children with Attention-Deficit/Hyperactivity Disorder, Pediatrics, vol. 104, No. 6, Dec. 1999.
Petition to Withdraw Application from Issue Pursuant to 37 CFR 1.313(c)(2) dated Oct. 16, 2007.
Physicians' Desk Reference: Adderall, 51st Ed. (1997).
Physicians' Desk Reference: Adderall, 56th Ed. (2002).
Physicians' Desk Reference: Dexedrine 56th Ed. (2002).
Physicians' Desk Reference: Ritalin, 56th Ed. (2002).
Plaintiff Shire LLC's Responses to Interrogatories No. 1-13 in Shire LLC v. Colony Pharmaceuticals, Inc., in the United States District Court for the District of Maryland, Case No. 1:07-cv-00718-CCB, Jun. 6, 2007.
Plaintiffs Shire Laboratories, Inc.'s and Shire LLC's Reply to Defendant Andrx Pharmaceuticals, LLC's Counterclaims, in the United States District Court for the Southern District of Florida, Miami Division, Case No. 07-22201-CIV-Cooke/Brown, Sep. 24, 2007.
Pozzi, et al, The Time Clock system: a new oral dosage form for fast and complete release of drug after a predetermined lag time,: Journal of Controlled Release, 31:99-108 (1994).
Prescribing Information: Dexedrine, brand of dextroamphetamine sulfate (2001).
R. Bianchini & C. Vecchio, Oral Controlled Release Optimization of Pellets Prepared by Extrusion-Spheronization Processing, IL Farmaco 44(6), 645-654, 1989.
Rambali, et al., Using experimental design to optimize the process parameters in fluidized bed granulation on a semi-full scale, International Journal of Pharmaceutics 220 (2001) 149-160.
Remington: The Science and Practice of Pharmacy, Basic Pharmacokinetics, 16th Ed. (1980), 693.
Remington: The Science and Practice of Pharmacy, Elutriation, 20th Ed. (2000), 690.
Remington's Pharmaceutical Sciences, Fifteenth Edition (1975) 1624-1625.
Rong-Kun Chang and Joseph R. Robinson, Sustained Drug Release from Tablets and Particles Through Coating, Pharmaceutical Dosage Forms: Tablets (Marcel Dekker, Inc. 1990), 199-302.
Rong-Kun Chang, A Comparison of Rheological and Enteric Properties among Organic Solutions, Ammonium Salt Aqueous Solutions, and Latex Systems of Some Enteric Polymers, Pharmaceutical Technology, Oct. 1990.
Rosen et al., Absorption and Excretion of Radioactively Tagged Dextroamphetamine Sulfate from a Sustained-Release Preparation, Jama, vol. 194, No. 11, Dec. 13, 1965, 145-147.
Rosen, et al., Absorption and Excretion of Radioactively Tagged Dextroamphetamine Sulfate From a Sustained-Release Preparation, Journal of the American Medical Association, Dec. 13, 1965, vol. 194, No. 11, 1203-1205.
Rudnic Deposition Transcript, Jul. 28, 2004.
Schaffer Deposition Transcript, Aug. 17, 2005.
Scheiffele, et al., Studies Comparing Kollicoat MAE 30 D with Commercial Cellulose Derivatives for Enteric Coating on Caffiene Cores, Drug Development and Industrial Pharmacy, 24(9), 807-818 (1998), 807-818.
Second Amended Complaint for Patent Infringement and Declaratory Relief in Shire Laboratories, Inc. v. Andrx Pharmaceuticals, LLC, in the United States District Court for the Southern District of Florida, Miami Division, Case No. 07-22201-CIV-Cooke/Brown, Nov. 15, 2007.
Serajuddin, et al., Selection of Solid Dosage Form Composition through Drug-Excipient Compatibility Testing, Journal of Pharmaceutical Sciences vol. 88, No. 7, Jul. 1999, 696-704.
Shargel;. Pharmacokinetics of Oral Absorption, Applied Biopharmaceutics & Pharmacokinetics. 5th Ed. (2005), 164-166.
Sheen et al., Aqueous Film Coating Studies of Sustained Release Nicotinic Acid Pellets: An In-Vitro Evaluation, Drug Development and Industrial Pharmacy, 18(8), 851-860 (1992).
Shire Laboartories Inc.'s Opposition to Barr Laboratories' Motion to Amend Its Answers and Counterclaims, Sep. 15, 2004.
Slattum, et al., Comparison of Methods for the Assessment of Central Nervous System Stimulant Response after Dextroamphetamine Administration to Healthy Male Volunteers, J. Clin Pharmacol 1996; 36: 1039-1050.
Sprowls' American Pharmacy: An Introduction to Pharmaceutical Techniques and Dosage Forms, 7th Ed. (1974), 387-388.
Sriamornsak, et al., Development of sustained release theophylline pellets coated with calcium pectinate, Journal of Controlled Release 47 (1997) 221-232.
Stevens, et al., Controlled, Multidose, Pharmacokinetic Evaluation of Two Extended-Release Carbamazepine Formulations (Carbatrol and Tegretol-XR), Journal of Pharmaceutical Sciences vol. 87, No. 12, Dec. 1998, 1531-1534.
Supplemental Expert Report of Harry G. Brittain, PhD, FRSC in Shire LLC v. Colony Pharmaceuticals, Inc., in the United States District Court for the District of Maryland, Case No. 1:07-cv-00718, Feb. 15,2008.
Teva Notice letter: Feb. 21, 2005.
Teva Notice letter: Jun. 1, 2005.
The Merck Index: Amphetamine, 12th Ed., 620.
The Merck Index: Amphetamine, 13th Ed., (2001), 97, 1089.
The United States Pharmacopeia 23, National Formulary 18 (1995) pp. 1791-1799.
The United States Pharmacopeia 26, National Formulary 21 (2003) pp. 2157-2165.
The United States Pharmacopeia 27, National Formulary 22 (2004) pp. 2302-2312.
Transcrip of Richard A. Couch 30(b)(6) Deposition in Shire LLC vs. Sandoz Inc. in the United States District Court for the District of Colorado, Dec. 14, 2007.
Transcript of Beth A. Burnside Deposition in Shire LLC v. Colony Pharmaceuticals, Inc., in the United States District Court for the District of Maryland, Case No. 1:07-cv-00718-CCB, Nov. 9, 2007.
Transcript of Beth A. Burnside Deposition in Shire LLC vs. Sandoz Inc. in the United States District Court for the District of Colorado, Case No. 07-CV-001197-EWN-CBS, Nov. 30, 2007.
Transcript of Kimberly Fiske Farrand Deposition in Shire, LLC v. Sandoz, Inc. in the United States District Court of Colorado, Dec. 4, 2007.
Transcript of Richard A. Couch Deposition in Shire LLC v. Colony Pharmaceuticals, Inc., in the United States District Court for the District of Maryland, Case No. 1:07-cv-00718-CCB, Nov. 15, 2007.
Transcript of richard Rong-Kun Chang in Shire LLC v. Colony Pharmaceuticals, Inc., in the United States District Court for the District of Maryland, Case No. 1:07-cv-00718-CCB, Nov. 20, 2007.
Treacy Deposition Transcript, Aug. 31, 2004.
Treatise on Controlled Drug Delivery, pp. 185-199 (Agis Kydonieus ed. 1992).
Tulloch, et al., SL1381 (Adderall XR), a Two-component, Extended-Release Formulation of Mixed Amphetamine Salts: Bioavailability of Three Test formulations and Comparison of Fasted, Fed, and Sprinkled Administration, PHARMACOTHERAPY vol. 22, No. 11. (2002), 1405-1415.
US 6,034,101, 3/2000, Gupta et al. (withdrawn)
Vasilevska, et al., Preparation and Dissolution Characteristics of Controlled Release Diltiazem Pellets, Drug Development and Industrial Pharmacy, 18(15), 1649-1661 (1992).
Walia et al., "Preliminary Evaluation of an Aqueous Wax Emulsion for Controlled-Release Coating," Pharmaceutical Development and Technology, 3(1):103-113-(1998).
Watano, et al., Evaluation of Aqueous Enteric Coated Granules Prepared by Moisture Control Method in Tumbling Fluidized Bed Process, Chem. Pharm. Bull. 42(3) 663-667 (1994).
Wesdyk, et al., Factors affecting differences in film thickness of beads coated in fluidized bed units, International Journal of Pharmaceutics, 93 101-109, (1993).
Wigal, et al., Evaluation of Individual Subjects in the Analog Classroom Setting; II. Effects of dose of amphetamine (Adderall), Psychopharmacology Bulletin, vol. 34, No. 4, pp. 833-838, 1998.
Wilding, et al., "Gastrointestinal Transit and Systemic Absorption of Captopril from a Pulsed-Release Formulation," Pharmaceutical Research, 9(5):654-657 (1992).
Wouessidjewe, Aqueous polymethacrylate Dispersions as Coating Materials for Sustained and Enteric Release Systems, S.T.P. Pharma Sciences 7(6) 469-475 (1997).
Xin Xu and Ping I. Lee, "Programmable Drug Delivery from an Erodible Association Polymer System," Pharmaceutical Research, 10(8):1144-1152 (1993).

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US20030124188A1 (en) 2003-07-03
JP2002527468A (en) 2002-08-27
AU1214500A (en) 2000-05-08
US6605300B1 (en) 2003-08-12
USRE41148E1 (en) 2010-02-23
CA2348090C (en) 2004-04-13
EP1977736A1 (en) 2008-10-08
EP1123087A1 (en) 2001-08-16
DE69940673D1 (en) 2009-05-14
US20010055613A1 (en) 2001-12-27
JP2008303223A (en) 2008-12-18
EP1123087A4 (en) 2004-02-11
WO2000023055A9 (en) 2000-08-31
US6322819B1 (en) 2001-11-27
WO2000023055A1 (en) 2000-04-27
EP1123087B1 (en) 2009-04-01
CA2348090A1 (en) 2000-04-27
ES2323910T3 (en) 2009-07-27
US20040219213A1 (en) 2004-11-04

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