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Wo 2008/021394 A2 (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (43) International Publication Date (10) International Publication Number 21 February 2008 (21.02.2008) PCT WO 2008/021394 A2 (51) International Patent Classification: (74) Agent: DAVIDSON, Clifford, M.; Davidson, Davidson & A61K 8/37 (2006.01) Kappel, LLC, 485 Seventh Avenue, 14th Floor, New York, NY 10018 (US). (21) International Application Number: (81) Designated States (unless otherwise indicated, for every PCT/US2007/0 18062 kind of national protection available): AE, AG, AL, AM, AT,AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, CA, CH, (22) International Filing Date: 15 August 2007 (15.08.2007) CN, CO, CR, CU, CZ, DE, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, (25) Filing Language: English IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, MW, (26) Publication Language: English MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, SV, SY, (30) Priority Data: TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, 60/837,607 15 August 2006 (15.08.2006) US ZM, ZW 60/837,606 15 August 2006 (15.08.2006) US 60/842,359 6 September 2006 (06.09.2006) US (84) Designated States (unless otherwise indicated, for every 60/849,006 4 October 2006 (04. 10.2006) US kind of regional protection available): ARIPO (BW, GH, GM, KE, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, MD, RU, TJ, TM), (71) Applicant (for all designated States except US): THER- European (AT,BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, AQUEST BIOSCIENCES, LLC [US/US]; P.O. Box FR, GB, GR, HU, IE, IS, IT, LT,LU, LV,MC, MT, NL, PL, 1266, Blue Bell, PA 19422 (US). PT, RO, SE, SI, SK, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG). (72) Inventor; and (75) Inventor/Applicant (for US only): BABUL, Najib Published: [US/US]; 146 Medinah Drive, Blue Bell, PA 19422-3212 — without international search report and to be republished (US). upon receipt of that report (54) Title: PHARMACEUTICAL FORMULATIONS OF CANNABINOIDS AND METHOD OF USE (57) Abstract: The present invention is directed to pharmaceutical compositions of cannabinoid agonists and the use thereof for preventing or minimizing the risk of cannabinoid agonist abuse and/or cannabinoid agonist toxicity from either intentional or unin- tentional tampering. The present invention is also directed at a method of preventing or minimizing the risk of cannabinoid agonist abuse and/or cannabinoid agonist toxicity from either intentional or unintentional tampering. PHARMACEUTICAL FORMULATIONS OF CANNABINOIDS AND METHOD OF USE FIELD OF THE INVENTION [0001] The present invention is in the field of oral compositions of abuse deterrent cannabinoids and the use thereof. BACKGROUND OF THE INVENTION [0002] Marijuana, often called "pot", "grass", "reefer", "weed", "herb", "mary jane" or "mj" is a greenish-gray mixture of the dried, shredded leaves, stems, seeds, and flowers of Cannabis sativa, the hemp plant. Most users smoke marijuana in hand-rolled cigarettes called "joints", among other names; some use pipes or water pipes called "bongs". Marijuana cigars called "blunts" have also become popular. To make "blunts", users slice open cigars and replace the tobacco with marijuana, often combined with another drug, such as "crack" cocaine. Marijuana also is used to brew tea and is sometimes mixed into foods. [0003] The major active chemical in marijuana is delta-9- tetrahydrocannabinol (THC), which causes the mind-altering effects of marijuana intoxication. The amount of THC (which is also the psychoactive ingredient in hashish) determines the potency and, therefore, the effects of marijuana. Between 1980 and 1997, the THC content of marijuana available in the United States rose dramatically. [0004] Marijuana is the most commonly used illicit drug in the United States. More than 94 million Americans (40 percent) age 12 and older have tried marijuana at least once, according to the 2003 National Survey on Drug Use and Health (NSDUH). Marijuana use is widespread among adolescents and young adults. It is reported that in 2004, 16 percent of 8th-graders volunteered that they had tried marijuana, and 6 percent were current users (defined as having used the drug in the 30 days preceding the survey). Among 10th- graders, 35 percent had tried marijuana sometime in their lives, and 16 percent were current users. As would be expected, rates of use among 12th-graders were higher still. Forty-six percent had tried marijuana at some time, and 20 percent were current users. [0005] The Drug Abuse Warning Network (DAWN), a system for monitoring the health impact of drugs, estimated that, in 2002, marijuana was a contributing factor in over 119,000 emergency department (ED) visits in the United States, with about 15 percent of the patients between the ages of 12 and 17, and almost two-thirds male. [0006] In 2002, the National Institute of Justice's Arrestee Drug Abuse Monitoring (ADAM) Program, which collects data on the number of adult arrestees testing positive for various drugs, found that, on average, 4 1 percent of adult male arrestees and 27 percent of adult female arrestees tested positive for marijuana. On average, 57 percent of juvenile male and 32 percent of juvenile female arrestees tested positive for marijuana. [0007] Cannabis use is world-wide public health issue. According to the United Nations Office for Drug Control and Crime Prevention (UNODCCP), Marijuana is the most widely used illicit drug in the world. It has been estimated that one in 11 cannabis users will become dependent (Anthony et al., Clin Psychopharmacol, 1994); rates of cannabis dependence in several countries (e.g., Australia, USA, South Africa) have increased substantially over the past decade (Bhana et al., S Afr Med J, 2002; SAMHSA, 2003), as well as the number of individuals seeking treatment (Stephens et al., Clin Psychol, 1993; Treatment Episode Data Set, 2002). [0008] The principal psychoactive constituent of marijuana, THC, was not definitively identified until 1964 (Gaoni and Mechoulam, J Am Chem Soc, 1964). Unfortunately, marijuana is not a good source of THC due to the difficulties in isolation and purification. The development of a practical synthetic pathway (Razdan et al., Experientia, 1972) was a major boost to the subsequent pharmacological characterization of the effects of marijuana and synthetic cannabinoids. Advances in chemistry, behavioral pharmacology, molecular pharmacology and neurobiology have facilitated the identification and characterization of an endogenous cannabinoid system. [0009] Initial evidence of a cannabinoid receptor came from work that demonstrated enantioselectivity for a number of the effects of THC (Edery et al., Arzneim-Forsch, 1972; Little et al., Pharmacol Biochem Behav, 1989; Martin et al., Life Sci, 1981). More direct evidence for the receptor emerged from the work of Devane et al. (MoI Pharmacol, 1988) showing that a synthetic cannabinoid resulted in site specific avid binding in the brain. This and other discoveries raised the tantalizing possibility that an endogenous cannabinoid ligand may exist. [0010] The work of Mechoulam resulted in the isolation of anandamide, a derivative of arachidonic acid. This endogenous ligand competed for cannabinoid receptor. Similar to THC, it inhibited electrically stimulated contractions in the murine vas deferens and produced pharmacological effects such as antinociception, catalepsy, hypomotility, hypothermia. [0011] The endogenous cannabinoids or endocannabinoids are all eicosanoids. Examples include N-arachidonoylethanolamine (anandamide) and 2- arachidonoyl glycerol. Endocannabinoids, together with cannabinoid CBi and CB2 receptors constitute the endocannabinoid system. The discovery of this endocannabinoid system has spurred research directed at elucidating the physiologic and pathophysiologic roles of the system and, importantly, at identifying targets for pharmacologic intervention in pathologic states. [0012] It is now known that mammalian tissues express at least two cannabinoid receptors, both of which are G-protein coupled. These are CBi receptors and CB receptors. [0013] Although CBi receptors are expressed by some non-neuronal cells, including the pituitary, immune cells, and reproductive tissue, they are found primarily in peripheral and central nerve terminals where they mediate inhibition of neurotransmitter release. CBi receptors are expressed predominantly in the CNS with especially high levels in cerebellum, hippocampus and basal ganglia. Indeed, of all neurotransmitters and hormone receptors, the CBi receptor is by far the most abundant. CBi receptors are also expressed to a much lesser extent in the peripheral nervous system as well as on the cells of the immune system, in the testis, heart and vascular tissues. [0014] CB receptors -ire found primarily on immune and hematopoietic cells outside (and also within) the central nervous system, where they appear to modulate cytokine release and immune cell migration. [0015] Studies using CBi and CB receptor knockout mice indicate that some of the effects of endocannabinoids are not mediated by either CBi or CB receptors, suggesting the existence of additional yet to be identified sites of action. Some cannabinoid effects resist classification as either CBi and CB - mediated. Although some of these effects may not
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