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US 2008 OO69871 A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2008/0069871 A1 Vaughn et al. (43) Pub. Date: Mar. 20, 2008 (54) HYDROPHOBC ABUSE DETERRENT filed on Aug. 30, 2006. Provisional application No. DELIVERY SYSTEM 60/871,504, filed on Dec. 22, 2006. Provisional appli cation No. 60/824,057, filed on Aug. 30, 2006. Pro (76) Inventors: Jason M. Vaughn, Round Rock, TX visional application No. 60/903,235, filed on Feb. 22, (US); Michael M. Crowley, Austin, TX 2007. Provisional application No. 60/893,825, filed (US); Feng Zhang, Austin, TX (US); on Mar. 8, 2007. Provisional application No. 60/893, John J. Koleng, Austin, TX (US); 798, filed on Mar. 8, 2007. Justin M. Keen, Round Rock, TX (US); Justin R. Hughey, Austin, TX Publication Classification (US) (51) Int. Cl. Correspondence Address: A6II 47/30 (2006.01) MEYERTONS, HOOD, KIVLIN, KOWERT & A6II 47/38 (2006.01) GOETZEL, P.C. A6IR 9/14 (2006.01) P.O. BOX 398 A 6LX 9/52 (2006.01) AUSTIN, TX 78767-0398 (US) A6IP 25/04 (2006.01) (52) U.S. Cl. ......................... 424/456; 424/484; 424/487: (21) Appl. No.: 11/781,008 514/772.6; 514/781 (22) Filed: Jul. 20, 2007 (57) ABSTRACT Related U.S. Application Data Disclosed herein are oral dosage forms of therapeutic agents that are resistant to abuse and methods of their formulation. (60) Provisional application No. 60/820,091, filed on Jul. In particular, oral dosage forms that are resistant to disso 21, 2006. Provisional application No. 60/824,042, lution in aqueous solutions of ethanol are described. Patent Application Publication Mar. 20, 2008 Sheet 1 of 13 US 2008/0069871 A1 to cr) s s e d O ld O S S wn w eSeefe eIOZepluodleM% Patent Application Publication Mar. 20, 2008 Sheet 2 of 13 US 2008/0069871 A1 s S s S s s S S s S S eSeefe, fin IC 9% Patent Application Publication Mar. 20, 2008 Sheet 3 of 13 US 2008/0069871 A1 eSeele GnuO % Patent Application Publication Mar. 20, 2008 Sheet 4 of 13 US 2008/0069871 A1 O S & wn CY) S. Q Q O CN was Q S. O to o S O S. cy KNS s s s S S O S s eSeefe findG 9% Patent Application Publication Mar. 20, 2008 Sheet 5 of 13 US 2008/0069871 A1 O O. O. Q O. O. O. O. O O S O) OO N O lc). Yi cr) CN w CS eSeeley fin IG 9% Patent Application Publication Mar. 20, 2008 Sheet 6 of 13 US 2008/0069871 A1 O O. O. O. O. O. s O) OO N CO lic) Nr eSeefe fruO 9% Patent Application Publication Mar. 20, 2008 Sheet 7 of 13 US 2008/0069871 A1 g S S 8Seefe fin IC 9% Patent Application Publication Mar. 20, 2008 Sheet 8 of 13 US 2008/0069871 A1 S. S. S O S O v. CX lc) S CN l g O N O CN g S isS O) SN O w O Q Q Q Q O Q s O) CO, N, O O. W. C.) eSeefe, 6nuO % Patent Application Publication Mar. 20, 2008 Sheet 9 of 13 US 2008/0069871 A1 Q Q Q Q Q O O) OO N CO lay Nir eSeefe fin IG 9% Patent Application Publication Mar. 20, 2008 Sheet 10 of 13 US 2008/0069871 A1 s s s s S O S eSeeley findC 94 Patent Application Publication Mar. 20, 2008 Sheet 11 of 13 US 2008/0069871 A1 g O. O. O. O. O. O. O. O. O. O. S O) OO. N. O. l.c.) CS eSeefe fruG 9% Patent Application Publication Mar. 20, 2008 Sheet 13 of 13 US 2008/0069871 A1 cye 3 S s S O O S. S CN S eSeeled 6nuG 9% US 2008/0069.871 A1 Mar. 20, 2008 HYDROPHOBC ABUSE DETERRENT DELIVERY 0008. The difficulty in the art is that it is desirable among SYSTEM drug abusers to bypass the extended release characteristics of oral dosage forms. By negating the controlled release PRIORITY CLAIM mechanisms of the dosage form, the abuser is able to 0001) This application claims the benefit of U.S. Provi produce a quick and intense rush of drug into the brain that sional Application No. 60/820,091 entitled “Abuse Deter results in a high. Abusers have found many methods by rent Delivery System,” filed Jul. 21, 2006 and U.S. Provi which the extended release characteristics of certain oral sional Application No. 60/824,042 entitled “Hydrophobic dosage forms can be bypassed. These include: (i) intrave Abuse Deterrent Delivery System,” filed Aug. 30, 2006 and nous injection of dissolved tablets or capsules, (ii) inhala U.S. Provisional Application No. 60/871,504 entitled tion/nasal Snorting of crushed tablets or capsules, (iii) chew “Hydrophobic Abuse Deterrent Delivery System,” filed Dec. ing tablets or capsules and (iv) dissolving of tablets or 2, 2006 and U.S. Provisional Application No. 60/824,057 capsules in alcoholic beverages followed by oral adminis entitled “Hydrophilic Abuse Deterrent Delivery System” tration. filed Aug. 30, 2006 and U.S. Provisional Application No. 0009 Abuse of narcotic substances is particularly prob 60/903,235 entitled “Hydrophilic Abuse Deterrent Delivery lematic. Such drugs are highly habit forming when misused System” filed Feb. 22, 2007 and U.S. Provisional Applica and thus are in high demand by drug abusers. In contrast, tion No. 60/893,825 entitled “Hydrophobic Abuse Deterrent there are numerous legitimate users of narcotic Substances Delivery System For Opioid Agents' filed Mar. 8, 2007 and that need oral dosage forms that release large quantities of U.S. Provisional Application No. 60/893,798 entitled “Hydrophilic Abuse Deterrent Delivery System For Opioid narcotic over an extended period of time for the treatment of Agents' filed Mar. 8, 2007. extreme pain. 0010 Oral formulations that deter abuse have also been BACKGROUND OF THE INVENTION suggested. U.S. Pats. No. 5,747,058 and 5,968,542 and U.S. 0002) 1. Field of the Invention Publication No. 2004.01611382 disclose an oral drug deliv 0003. The invention generally relates to pharmaceutical ery system based on the use of therapeutic agents suspended delivery systems and methods of their use, in particular oral in high viscosity liquid carrier material. dosage systems for the delivery of drugs that are resistant to 0011. The U.S. Publication No. 2003.0118641 discloses abuse. controlled-release opioid delivery compositions that are resistant to extraction with commonly-available solvents. 0004 2. Description of the Relevant Art The formulation between 30 and 65% of a matrix forming 0005 Drug formulations for the oral delivery of pharma polymer and between 5 and 15% of an ionic exchange resin. ceuticals have been used for centuries. More recently, However the disclosed formulations are prepared as tablets numerous compositions and methods have been developed of compressed powder that can be readily crushed. This fails for the controlled release of pharmaceuticals after oral to deter methods of drug abuse involving nasal inhalation. delivery. Such extended-release characteristics can be useful 0012. Other abuse deterrent systems include oral dosage for many reasons. One reason is that extended-release deliv ery systems can limit the number of doses a patient must forms that include an opioid and an opioid antagonist that is take over a period of time thus improving compliance with released when the dosage form is tampered with. Examples a dosing regimen. Another reason is that extended release of this approach can be found at U.S. Pat. Nos. 6,696,088, delivery systems can provide a steady dose of medication to 6,696,066, 6,627,635, 6,326,027 and 6,228,863. a patient, thereby avoiding Sudden increases and decreases 0013 U.S. Publication No. 2004.0052731 discloses oral in the level of medication being delivered to the blood dosage forms of drugs that have been modified to increase stream. Controlled release of pharmaceuticals is particularly their lipophilicity entrapped in coated microparticles critical with drugs that are habit forming, as the controlled wherein the coatings render the microparticles insoluble or release of the medication can significantly reduce the like poorly soluble in various solvents. The formulations can still lihood of a patient developing an addiction to the Substance. be crushed, but the formulations are intended to prevent 0006. One common method of producing a controlled immediate release of the drug even when crushed. release oral dosage form is to Surround the drug with a 0014. Therefore there remains a significant need in the art coating or barrier of a hydrophobic Substance Such as a for oral dosage forms that are resistant to attempts by polymeric coating. These coatings or barriers can be potential abusers to bypass the controlled or extended designed to dissolve gradually when brought into contact release characteristics of conventional oral dosage forms. In with digestive fluids thus producing a slow and steady particular, oral dosage forms are needed that are resistant to release of a drug when it is ingested. crushing and dissolution in water or aqueous alcohol solu 0007. Other approaches that have been developed include tions such as alcoholic beverages. the methods disclosed in U.S. Pat. Nos. 6,261,599, 6,335, SUMMARY OF THE INVENTION 033, 6,706,281 and 6,743,442 wherein a drug is mixed with a water-insoluble retardant and optionally with binders 0015. In certain embodiments, the invention relates to and/or plasticizers. The mixture is then heated and extruded oral dosage forms of a therapeutic agent that are abuse into narrow Strands which are cut into particles having a size deterrent.
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  • FEASTING THYME Serves Four, Available After 3Pm PROTEIN GARDEN SIDES Choose One Choose Two

    FEASTING THYME Serves Four, Available After 3Pm PROTEIN GARDEN SIDES Choose One Choose Two

    KIDS MENU DESSERT 12 and under Turkey and Cheese Sandwich Ice Cream Sandwich roasted turkey with side of fruit 3.99 Pastry Art’s lemon rosemary cookies with vanilla ice cream 3.49 AB&J Sandwich almond butter and homemade blueberry Cake Cups jam with seasonal fruit 3.99 Pastry Art’s daily selection 2.99 Spaghetti and Meatballs 4.99 Today’s Cheese Plate Grilled Chicken Dippers selection of three cheeses 9.99 served with choice of side 4.99 Flounder Cakes served with choice of side 4.99 DRINKS Simple Peas Fountain/Tea 1.99 Corn Polenta Bites Succotash with Herb Butter Orange Blossom Lemonade 2.49 + .99 refills Zucchini Salad Apples with Almond Butter Fresh Spa Water 2.99 Fresh Fruit Beer and wine served all day, cocktails served after 4pm. real food, good company FEASTING THYME serves four, available after 3pm PROTEIN GARDEN SIDES choose one choose two R&R Grilled Chicken 26.99 House Salad Spice Rubbed Chicken 26.99 Succotash with Herb Butter Corn Polenta Cake Roasted Turkey 26.99 Sweet and Spicy Slaw Flounder Cakes 29.99 Zucchini Salad Braised Beef 29.99 Humble Green Peas realandrosemary.com Charred Carrots with Thyme Spaghetti and Meatballs 25.99 Open daily from 11am to 9pm Located across from Pastry Art and the Aloft served with house salad and toast 1922 29th Ave S, Homewood, AL 35209 | 205-820-7100 SANDWICHES GARDEN SIDES served with one garden side 2.49 each Succotash with Herb Butter SNACKS Grilled Chicken grilled chicken, roasted portobello, Corn Polenta Cake collard pesto, charred red onion, Sweet and Spicy Slaw Collard Pesto Dip