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US 20170020873A1 (19) United States (2) Patent Application Publication (10) Pub. No.: US 2017/0020873 A1 Mitchell (43) Pub. Date: Jan. 26, 2017 (54) PHARMACEUTICAL COMPOSITIONS Publication Classification (71) Applicant:: …~~~ +. *e Inc., Arlington,- (51) A61RInt. Cl. 31/.505 (2006.01) A61 K. 3 1/137 (2006.01) (72) Inventor: Odes W. Mitchell, Arlington, TX (US) A61 K. 3 1/167 (2006.01) A61 K. 3 1/09 (2006.01) - A61 K 37/495 (2006.01) (21)21) Appl. No.:No 15/287,047s A61 K 31/485 (2006.01) 31, 21. A61 K. 3 1/135 (2006.01) (22) Filed: Oct. 6, 2016 A61 K. 3 I/4402 (2006.01) Related U.S. Application- - - Dat ( 52) U.S. CI. elate pplication Data CPC ........... A61K 31/505 (2013.01); A61K 31/135 (63) Continuation of application No. 14/733,731, filed on (2013.01); A61K 31/137 (2013.01); A61 K Jun. 8, 2015, now Pat. No. 9,463,191, which is a 31/4402 (2013.01); A61K 31/09 (2013.01); continuation of application No. 13/703,584, filed on A61K 31/495 (2013.01); A61K 31/485 Feb. 2, 2013, now Pat. No. 9,050,289, filed as appli- (2013.01); A61K 31/167 (2013.01) cation No. PCT/US2011/040231 on Jun. 13, 2011. (60) Provisional application No. 61/354,053, filed on Jun. (57) ABSTRACT 11, 2010, provisional application No. 61/354,057, A composition of an antitussive, a decongestant, or an filed on Jun. 11, 2010, provisional application No. antihistamine to treat upper respiratory and oral pharyngeal 61/354,061, filed on Jun. 11, 2010. congestion and related symptoms in a patient. US 2017/0020873 A1 Jan. 26, 2017 chloride, diprodualone camsilate, dixyrazine, doxylamine metaraminol, phenylephrine, tyraine, hydroxyamphetamine, succinate, eprozinol dihydrochloride, etodroxizine ritodrine, prenalterol, methoxyamine, albuterol, amphet dimaleate, etybenzatropine bromhydrate, etybenzatropine amine, methamphetamine, benzphetamine, ephedrine, phe hydrochloride, etymemazine hydrochloride, fenethazine nylpropanolamine, mephentermine, phentermine, fenflu hydrochloride, fenoxazoline hydrochloride, fenpentadiol, ramine, propylhexedrine, diethylpropion, phenmetrazine, flunarizine hydrochloride, flupentixol decanoate, flupentixol phendimetrazine, oxymetazoline, xylometazoline, and pseu dihydrochloride, histapyrrodine hydrochloride, hydroxyzine doephedrine. dihydrochloride, hydroxyzine embonate, indoramine hydro [0020] It should be understood that an effective amount of chloride, isothipendyl hydrochloride, ketotifene fumarate, the antitussive and the decongestant generally vary with the levocabastine hydrochloride, levomepromazine, levomepro particular antitussive and decongestant chosen. In addition, mazine hydrochloride, levomepromazine embonate, an effective amount depends upon many other factors, such levomepromazine maleate, loratadine, maprotiline hydro as known differences in pharmacokinetic parameters (ab chloride, maprotiline mesilate, maprotiline resinate, sorption, distribution and clearance) regardless of the cause. meclozine hydrochloride, mecysteine hydrochloride, medi For example, in a patient with a renal dysfunction or foxamine fumarate, mefenidramium metilsulfate, mepyra disorder, the effective dose of the antihistamine, the antitus mine maleate, meduitazine, methaqualone, methdilazine sive, and the decongestant is generally half of an effective hydrochloride, metixene hydrochloride, mizolastine, moxi dose for a patient without renal dysfunction. sylyte hydrochloride, niaprazine, orphenadrine hydrochlo [0021] While the present composition includes an antitus ride, oxaflumazine disuccinate, oxatomide, oxolamine ben sive, a decongestant, and an antihistamine, the present zilate, oxolamine citrate, oxomemazine, oxomemazine composition is not so limited and may include other com hydrochloride, parathiazine teoclate, perimetazine, pheni ponents. These components include conventional excipients, ramine maleate, phenoxybenzamine hydrochloride, phenyl useful and/or desirable to render the composition suitable or toloxamine, phenyltoloxamine citrate, pimethixene, pipoti attractive for consumption and use. Excipients providing azine, pipretecol dihydrochloride, pizotifene malate, physical and aesthetic properties for formulation or delivery prednazoline, profenamine hydrochloride, promethazine, of the composition are desirable. For example, with respect promethazine hydrochloride, promethazine embonate, pro to physical properties, ingredients imparting desirable and methazine polyvinylbenzene-metacrylate, propiomazine, acceptable hardness, disintegration properties, dissolution terfenadine, thenalidine tartrate, thenyldiamine hydrochlo rate for release of therapeutic components, stability, and size ride, thiazinamium metilsulfate, thonzylamine hydrochlo to effectively deliver the composition may be included. ride, tripelennamine hydrochloride, triprolidine hydrochlo Disintegrants may be included for the purposes of facilitat ride, and tymazoline hydrochloride, and combinations ing the breakup of a tablet after the tablet is administered to thereof. the patient. Examples of disintegrants include, but are not [0017] The antihistamine is included in an amount, per limited to, modified or unmodified starches such as corn dosage of the composition, sufficient to alleviate one or more starch, potato starch, wheat starch, or sodium cross-carmel histamine-mediated responses in a patient. Effective doses los. With respect to aesthetics, it may be desirable for the of the antihistamine will generally vary depending upon the composition to contain additives that appeal to the human antihistamine (s) administered. senses such as colorants, fragrances, texture modifiers, and/ [0018] The present composition also includes an antitus or flavorants. Additionally, many flavoring agents such as, sive. The term “antitussive”, as used herein, is intended to for example, fruit flavors, or sweeteners, such as sodium include any agent or active ingredient effective for cough saccharin, confectionery sugar, sucrose, xylitol, or combi suppression such as chlophedianol hydrochloride. These nations thereof, may be included. Additionally, suitable also include, but are not limited to, common opioid analge colorants including, for example, red beet powder, ferric sics such as hydrocodone, codeine, morphine, morphine oxide, FD&C dyes, or combinations thereof, may be related compounds including diacetylmorphine, oxymor included in the present compositions. Desirable excipients phone, hydromorphone, dextromethorphan, levorphanol, may also include buffering agents, surfactants, electrolytes, oxycodone, nalmefene, methadone, meperidine, pentazo and thixotropic agents. It should be understood that these cine, buprenorphine, nalbuphine, butorphanol, sufentanyl, other components should not affect the action or mechanism alfentanyl and propoxyphene, and opioid antagonists not of action of the antitussive, decongestant, and/or the anti structurally-related to morphine, such as nalorphine, nalox histamine in the composition. one, maltrexone and fentanyl. In one embodiment, the anti [0022] Excipients or formulations affecting the release tussive agent is hydrocodone or a pharmaceutically accept properties, mechanisms, and/or rates of the antitussive, the able salt form thereof, such as hydrocodone bitartrate. decongestant, and the antihistamine, from the composition [0019] The present composition also includes a deconges upon oral ingestion may be provided. For example, the tant. The term “decongestant” as used herein, is intended to composition may be formulated such that the release of the refer to any agent or ingredient, active for reducing or antitussive, the decongestant, and/or the antihistamine or eliminating congestion of the air passages by widening the other active ingredients from the composition is delayed for airway, and/or by stimulating the release of phlegm and a period of time or to survive a particular environment. mucus from these passages. Air passages may be widened by [0023] Advantageously, the composition may be formu reducing the swelling of the mucous membranes in the lated so as to prevent the release of the antitussive, the passage. Generally, sympathomimetic drugs have deconges decongestant, and/or the antihistamine in the stomach where tant properties. Examples of suitable decongestants include, they may likely be acidified, salted out and excreted from the without limitation, phenylethylamine, epinephrine, norepi body rather than absorbed into the circulation. For example, nephrine, dopamine, dobutamine, colterol, ethylnorepineph the composition may be coated with a coating to improve rine, isoproterenol, isoetharine, metaproterenol, terbutaline, absorption and render the composition more bioavailable US 2017/0020873 A1 Jan. 26, 2017 than it would otherwise be without the coating. Enteric and other blockage of air passages, the composition of the coatings or encapsulation-type coatings as known to one present invention includes the antitussive, the decongestant, skilled in the art are suitable for this purpose. In one and the antihistamine in amounts suitable for treating chil embodiment, a table or a capsule form of the composition is dren and adults alike. enterically coated so as to provide delayed-release and [0028] In yet another embodiment of the present inven sustained-release properties to the composition. Sustaining tion, there is provided methods of alleviating symptoms of upper respiratory and oral pharyngeal congestion by orally the release of individual active ingredients to the body over administering to a patient in need thereof a single dose of
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    USOO8603526B2 (12) United States Patent (10) Patent No.: US 8,603,526 B2 Tygesen et al. (45) Date of Patent: Dec. 10, 2013 (54) PHARMACEUTICAL COMPOSITIONS 2008. O152595 A1 6/2008 Emigh et al. RESISTANT TO ABUSE 2008. O166407 A1 7/2008 Shalaby et al. 2008/0299.199 A1 12/2008 Bar-Shalom et al. 2008/0311205 A1 12/2008 Habib et al. (75) Inventors: Peter Holm Tygesen, Smoerum (DK); 2009/0022790 A1 1/2009 Flath et al. Jan Martin Oevergaard, Frederikssund 2010/0203129 A1 8/2010 Andersen et al. (DK); Karsten Lindhardt, Haslev (DK); 2010/0204259 A1 8/2010 Tygesen et al. Louise Inoka Lyhne-versen, Gentofte 2010/0239667 A1 9/2010 Hemmingsen et al. (DK); Martin Rex Olsen, Holbaek 2010, O291205 A1 11/2010 Downie et al. (DK); Anne-Mette Haahr, Birkeroed 2011 O159100 A1 6/2011 Andersen et al. (DK); Jacob Aas Hoellund-Jensen, FOREIGN PATENT DOCUMENTS Frederikssund (DK); Pemille Kristine Hoeyrup Hemmingsen, Bagsvaerd DE 20 2006 014131 1, 2007 (DK) EP O435,726 8, 1991 EP O493513 7, 1992 EP O406315 11, 1992 (73) Assignee: Egalet Ltd., London (GB) EP 1213014 6, 2002 WO WO 89,09066 10, 1989 (*) Notice: Subject to any disclaimer, the term of this WO WO91,040 15 4f1991 patent is extended or adjusted under 35 WO WO95/22962 8, 1995 U.S.C. 154(b) by 489 days. WO WO99,51208 10, 1999 WO WOOOf 41704 T 2000 WO WO 03/024426 3, 2003 (21) Appl. No.: 12/701,429 WO WOO3,O24429 3, 2003 WO WOO3,O24430 3, 2003 (22) Filed: Feb.