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(12) Patent Application Publication (10) Pub. No.: US 2007/0141147 A1 Heil Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2007/0141147 A1 Heil Et Al US 200701.41 147A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2007/0141147 A1 Heil et al. (43) Pub. Date: Jun. 21, 2007 (54) SEQUENTIAL RELEASE Publication Classification PHARMACEUTICAL FORMULATIONS (51) Int. Cl. (75) Inventors: Matthew F. Heil, Duluth, GA A6II 3/55 (2006.01) (US); Glynn Wilson, Duluth, GA A63L/485 (2006.01) (US s s A6IR 9/22 (2006.01) A63/37 (2006.01) Correspondence Address: AOIN 31/08 (2006.01) PATREAL PABST (52) U.S. Cl. ........ 424/468; 514/282: 514/304: 514/649; PABST PATENT GROUP LLP 514/217.05: 514/731 400 COLONY SQUARE, SUITE 1200, 1201 s PEACHTREE STREET ATLANTA, GA 30361 (57) ABSTRACT A mixed-release tablet or capsule formulation including (73) Assignee: Auriga Laboratories, Inc. vehicles for the delivery of a plurality of drugs in various combinations of immediate release, extended release, and/or (21) Appl. No.: 11/461,238 delayed release modes over a predetermined time period 1-1. have been developed, which provide for controlled release (22) Filed: Jul. 31, 2006 not just of the drugs, but controlled release that is designed O O to create more effective coordination between the drugs Related U.S. Application Data being delivered. The drugs can be any medically and/or (60) Provisional application No. 60/752,057, filed on Dec. physiologically appropriate combination of drugs and active 21, 2005, provisional application No. 60/761,766, ingredients, preferably decongestant drugs, antihistamines, filed on Jan. 25, 2006, provisional application No. expectorants, antitussives, cough Suppressants, and drying 60/791,408, filed on Apr. 13, 2006. agents. US 2007/01.41 147 A1 Jun. 21, 2007 SEQUENTIAL RELEASE meta to the aliphatic side chain. The meta position affords PHARMACEUTICAL FORMULATIONS optimal activity. Phenylephrine (neo-synephrine) replaced an older preparation, Synephrine, in which the hydroxyl was CROSS-REFERENCE TO RELATED in the para position. Phenylephrine hydrochloride is avail APPLICATIONS able in the form of the levorotatory isomer, which is a white, odorless, non-hygroscopic, crystalline compound possess 0001 Priority is claimed to U.S. application Nos. 60/752, ing a bitter taste. Phenylephrine hydrochloride has a melting 057, filed Dec. 21, 2005; 60/761,766 filed Jan. 25, 2006; and point of 140-145° C. and is freely soluble in water and 60/791,408 filed Apr. 13, 2006 alcohol. Decongestant compounds in the form of their free bases as well as their pharmaceutically acceptable salts, e.g., FIELD OF THE INVENTION hydrochloride, citrate, maleate, tannate, etc., are used. Expectorants, such as guaifenesin, change a dry, unproduc 0002 The present invention provides a mixed-release tive cough to one that is more productive and less frequent. formulation that contains a plurality of active therapeutic Guaifenesin, known chemically as 3-(2-methoxyphenoxy)- agents and provides continuous immediate and/or extended 1.2-propanediol, is a crystalline powder, which is soluble in dosing and delayed dosing for a predetermined time period, water and alcohol. It is indicated in the USP Drug informa up to at least 12 hours. tion as an expectorant for the symptomatic relief of cough due to colds and minor upper respiratory infections. BACKGROUND OF THE INVENTION 0004 Phenylephrine may be present in amounts of 0003. Existing methods for the treatment of a variety of between about 15 and about 60 milligrams per capsule, conditions involve the administration of more than one preferably from about 5 milligrams to about 30 milligrams active agent using formulations that allow for immediate as per capsule, with half or less of that amount used in a well as controlled release. The drug delivery profiles of such pediatric form of the formulation. Delsym DM(R) (Novartis) formulations are simple, usually involving the immediate is an example of a Sustained-release dextromethorphan release of an active ingredient, followed by the sustained composition. The Sustained-release characteristics of the release of the same ingredient, or a different active ingre composition are achieved by the use of Small particles of an dient, delayed for a certain period of time. However, many ion-exchange resin bound to the dextromethorphan that of these formulations fail to take advantage of combining delay release of the drug in the gastrointestinal tract. How multiple controlled, delayed, or immediate release profiles ever, the bioavailability of dextromethorphan is relatively within a single preparation other than just combinations of low due to the strong bond between residual amounts of immediate and delayed release. In particular, present meth dextromethorphan and the ion exchange resin. The total ods for the treatment of cold or allergic rhinitis symptoms percentage of dextromethorphan released from dex rely upon a wide variety of agents, most principally anti tromethorphan-ion exchange resin complexes is incomplete, histamines (e.g., Chlorpheniramine), expectorants e.g., and under certain in vitro conditions it has been observed guaifenesin), decongestants (e.g., pseudoephedrine or phe that even after a twelve hour period of time, about 20% of nylephrine) and drying agents (e.g., the antisecretory drug dextromethorphan remains bound to the ion exchange resin. methScopolamine). Dextromethorphan is antitussive agent 0005 Examples of the preparation of sustained release used in many over-the-counter cold medications. It has an formulations of individual cough-cold medicines include opioid-like structure but, being a D-isomer, it does not U.S. Pat. No. 6,416,786 to Mulaye (sustained release for possess the analgesic or addictiveness of opioids. It acts mulation of guaifenesin); U.S. Patent Application Publica centrally to relieve cough, similar to opioids. It is active tion No. 20050152967 by Tengler et al. (mixed release against dry cough and does not exhibit significant expecto formulations of an expectorant for immediate release and a rant properties for productive cough. MethScopolamine decongestant for extended release); U.S. Pat. No. 6,955,821 nitrate is an anticholinergic and is a derivative of Scopola to Davis et al. (Sustained release formulation of guaifenesin mine. It possess the peripheral actions of the belladonna and at least one other drug, wherein guaifenesin is formu alkaloids, but does not exhibit the central actions because of lated for both immediate and extended release); and U.S. its inability to cross the blood-brain barrier. In cough-cold Pat. No. 6,372,252 Blume et al. (sustained release guaifen preparations, it is most often used for its anti-secretory effect esin formulations where guaifenesin is formulated for both on the upper respiratory system. However, methScopolamine immediate and extended release). has a relatively short plasma half-lie and needs an extended 0006 While some mixed release compositions have been release formulation to provide symptomatic relief over described, as discussed above, there is still a need in the art extended periods of time. Chlorpheniramine, often admin to create controlled release pharmaceutical formulations istered as the maleate salt, is a short-acting antihistamine with better sequential release characteristics that orchestrate (H1) compound that also has a short plasma half-life. Chlo the Symphony of symptomatic release agents to better fit the rpheniramine also requires an extended release formulation needs of patients Suffering from a cold, or those experienc to provide extended symptomatic relief in cough-cold for ing cold like symptoms in terms of decongestant, expecto mulations. Phenylephrine is an alpha agonist that acts as a rant and drowsiness characteristics. decongestant in cough-cold formulations. Phenylephrine 0007. Therefore it is an object of the present invention to also requires a longer acting formulation. Phenylephrine provide a formulation with a tighter control of different drug hydrochloride, also known as (S)-3-hydroxy-alpha(me release than what is achieved with an immediate release thylamino) methylbenzene methanol hydrochloride, is an Sustained release formulation. orally effective nasal decongestant. Phenylephrine is a syn 0008. It is a further object of the invention to provide a thetic, optically active sympathomimetic amine that has one formulation including an expectorant for immediate and hydroxyl group on the benzene ring. The hydroxyl group is extended release, and a cough suppressant for delayed and US 2007/01.41 147 A1 Jun. 21, 2007 extended release, wherein the release profiles of the ingre such that up to 50% of the antitussive active drug is released dients are orchestrated to better co-ordinate the production in immediate fashion over the first 1 to 4 hours, followed by and clearance of mucus and cough suppression. Sustained release of the antitussive drug, such that up to 100% of the antitussive active drug is released between 4 to SUMMARY OF THE INVENTION 12 hours. In another embodiment, the pharmaceutical for mulations include an expectorant for immediate and 0009. A mixed-release tablet or capsule formulation extended release, and a cough suppressant for delayed and including vehicles for the delivery of a plurality of drugs in extended release, wherein the release profiles of the ingre various combinations of immediate release, extended dients are orchestrated to better co-ordinate the production release, and/or delayed release modes over a predetermined and clearance of mucus and cough suppression. time period have been developed which provide for con 0011. The pharmaceutical formulation
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