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(12) Patent Application Publication (10) Pub. No.: US 2016/0279073 A1 Donsky Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2016/0279073 A1 Donsky Et Al US 20160279073A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2016/0279073 A1 Donsky et al. (43) Pub. Date: Sep. 29, 2016 (54) TERPENE AND CANNABINOID Publication Classification FORMULATIONS (51) Int. Cl. A63L/01 (2006.01) (71) Applicant: FULL SPECTRUM A63L/05 (2006.01) LABORATORIES, LTD., Dublin 2 A636/85 (2006.01) (IE) A63L/352 (2006.01) A63L/05 (2006.01) (72) Inventors: Marc Donsky, Denver, CO (US); A6II 47/36 (2006.01) Robert Winnicki, Denver, CO (US) A 6LX 9/27 (2006.01) A63L/045 (2006.01) (21) Appl. No.: 15/033,023 (52) U.S. Cl. CPC ............... A6 IK3I/01 (2013.01); A61K 9/127 (22) PCT Fed: Oct. 31, 2014 (2013.01); A61 K3I/015 (2013.01); A61 K 31/045 (2013.01); A61K 31/352 (2013.01); (86) PCT No.: PCT/B2O14/OO3156 A61 K3I/05 (2013.01); A61K 47/36 (2013.01); A61K 36/185 (2013.01) S 371 (c)(1), (2) Date: Apr. 28, 2016 (57) ABSTRACT The present invention provides stable, fast-acting liposome and micelle formulations of terpenes, hemp oil, cannabi Related U.S. Application Data noids, or mixtures of a cannabinoid and terpenes or hemp oil and cannabinoids that are Suitable for pharmaceutical and (60) Provisional application No. 61/898,024, filed on Oct. nutraceutical applications. Also provided are methods for 31, 2013. the manufacture of micelle and liposomal formulations. US 2016/0279.073 A1 Sep. 29, 2016 TERPENE AND CANNABINOID medical conditions, including glaucoma, AIDS wasting, FORMULATIONS neuropathic pain, treatment of spasticity associated with multiple Sclerosis, fibromyalgia and chemotherapy-induced PRIORAPPLICATION INFORMATION nausea. Additionally, THC has been reported to exhibit a therapeutic effect in the treatment of allergies, inflammation, 0001. The instant application claims the benefit of U.S. infection, epilepsy, depression, migraine, bipolar disorders, Provisional Patent Application 61/898,024, filed on Oct. 31, anxiety disorder, and drug dependency and withdrawal 2013. syndromes. THC is particularly effective as an anti-emetic FIELD OF THE INVENTION drug and is administered to curb emesis, a common side effect accompanying the use of opioid analgesics and anaes 0002 The present invention relates to liposomal formu thetics, highly active anti-retroviral therapy and cancer che lations of one or more terpenes, as well as a liposomal or a motherapy. micellar formulation of one or more terpenes in combination 0009. Like terpenes, cannabinoids are lipophilic and with one or more cannabinoids or an analog of a cannabi potentially acid-labile compounds. Because of their hydro noid. More specifically, the present invention relates to the phobic nature, cannabinoids are poorly absorbed systemi manufacture and use of Such formulations for medical, cally from oral dosage forms in the aqueous environment of pharmaceutical and nutraceutical applications. the gastrointestinal tract, and oral formulations of cannabi noids, therefore, exhibit low bioavailability. BACKGROUND OF THE INVENTION 0010. The present invention overcomes the drawbacks 0003 Terpenes and terpenoids are natural volatile non described above by providing a stable liposomal composi aromatic compounds found as components of essential oils tion of a terpene as well as stable liposomal and micellar present in many plants and contain a carbon and hydrogen compositions of a terpene-cannabinoid mixture. The inven (terpenes) or a carbon, hydrogen, and oxygen scaffold tive compositions are Suitable for medical, pharmaceutical (terpenoids). Terpenes and terpenoids have been used as and nutraceutical applications. In addition, the present fragrances and flavoring agents, as well as skin penetration invention provides stable liposomal compositions of hemp agents. Terpenes are classified by the number of isoprene oil as well as stable liposomal and micellar compositions repeat units present in their molecular structure. Thus, that contain a mixture of hemp oil and cannabinoid. The hemiterpenes represent a class of compounds which consist formulations according to the present invention are Suitable of a single isoprene unit. Monoterpenes, Such as geraniol, for medical, pharmaceutical and nutraceutical applications. limonene and terpineol, consists of two isoprene units and Also described is the use of such formulations for stimulat conform to a molecular formula CH. Sesquiterpenes ing intellectual activity and mental concentration, and to contain three isoprene units and have a molecular formula procure calming effects (Tambe Yet al., 1996, Planta Med. CH. Illustrative of this class are humulene, farmesene 62(5):469-70; Tembaro and Bartolato 2012, Recent Pat CNS and farnesol. Drug Discovery 7(1) 25-40). 0004 Diterpenes, such as cafestol, kahweol, cembrene and taxadiene (a precursor of taxol), have four isoprene SUMMARY OF THE INVENTION repeat units while sesterterpenes, such as geranylfarnesol, 0011. It is therefore an aspect of the invention to provide contain five isoprene units. solutions to the aforementioned deficiencies in the art. To 0005 Triterpenes containing six isoprene units are the this end the invention provides a stable liposomal formula structural precursors of Steroids. For instance, the triterpene tion of a primary, secondary or tertiary terpene in an aqueous squalene is a major constituent of shark liver oil that is used Solution. Illustrative of the class primary terpene are in the manufacture of lanosterol or cycloartenol. Sesquar C-pinene, C.-bisabolol, B-pinene, guaiene, guaiol, limonene, terpenes. Such as ferrugicadiol and tetraprenylcurcumene, myrcene or Ocimene. The amount of the primary terpene in contain seven isoprene units while tetraterpenes, such as the inventive formulation is 50% (w/w), while the amount of lycopene, monocyclic gamma-carotene, and alpha- and the secondary terpene is from about 30% to about 40% beta-carotenes contain eight isoprene units. Terpenes having (w/w) and the amount of the tertiary terpene is from about more than eight isoprene repeat units are referred to as 8% to about 10% (w/w) of the formulation. polyterpenes. Rubber, for instance, is a polyterpene which 0012. Each unique cultivar of Cannabis sativa may have consists of long chains of repeating isoprene units. a unique cannabinoid and cannabinoid-terpene profile. This 0006 More than 120 different types of terpenes have invention describes Primary, Secondary and Tertiary terpene been identified in extracts obtained from plants belonging to groups. Terpenes can be extracted, collected and encapsu the genus Cannabis. The concentration of each terpene, lated in liposomes or micelles. There is a growing body of however, has been shown to vary between the different plant research on the sedative and stimulatory properties of ter cultivars. penes, and on the organoprotective, anti-cancer and anti 0007 Terpenes have poor solubility in water, but are viral effects of individual and combinations of terpenes and readily soluble in non-aqueous and/or hydrophobic medium. essential oils. Certain terpenes are known to have medicinal Because of their lipophilic nature, terpenes can easily cross properties that have been utilized in aromatherapy, as well as the blood-brain barrier and interact with cell membranes by for sedative, analgesic, anti-inflammatory, antibiotic, anti binding to membrane receptors. fungal and mental stimulation. This invention includes 0008 Cannabinoids are compounds derived from Can unique groupings that have been observed in various culti nabis sativa, an annual plant in the Cannabaceae family. The vars of Cannabis sativa that may have medicinal value. plant contains about 60 cannabinoids. The most active 0013. In one embodiment, the stable inventive liposomal naturally occurring cannabinoid is tetrahydrocannabinol Suspensions can further comprise one or more cannabinoids (THC), which is used for the treatment of a wide range of or cannabinoid analogs. The average diameters of liposomes US 2016/0279.073 A1 Sep. 29, 2016 in a formulation according to the invention is in a range consisting of C-pinene, t-carophyllene, terpinolene, between 50 nm to 1000 nm and the final maximum concen ocimene, limonene and linalool and the tertiary terpene is tration of cannabinoids or cannabinoid analogues in the selected from the group consisting of B-pinene, t-carophyl above described formulation is from 0.01 g/liter to 100 lene, limonene, Ocimene, myrcene, C-pinene, bisabolol and g/liter. Any cannabinoids or cannabinoid analogues selected myrcene. The Suspension may further comprise trace from natural compounds, synthetic compounds, semi-syn amounts of one or more terpenes selected from the group thetic compounds, or mixtures thereof can be used in the consisting of C-humulene, C.-bisabolol, guaiene, limonene, claimed Suspension. Exemplary compounds within the class ocimene, 3-carene, B-pinene, C-pinene, myercene, guaiol, cannabinoids or cannabinoid analogues include without C-terpineol, terpinolene and linalool. limitation cannabinol, cannabidiol, A9-tetrahydrocannabi 0023 The invention also provides a stable, aqueous, nol, A-8-tetrahydrocannabinol, 11-hydroxy-tetrahydrocan liposomal Suspension comprising hemp oil and one or more nabinol, 11-hydroxy-A-9-tetrahydrocannabinol, levonant cannabinoids or cannabinoid analogues. Preferably, the can radol, A-11-tetrahydrocannabinol, tetrahydrocannabivarin, nabinoids or cannabinoid analogues in the inventive Suspen dronabinol, amandamide, nabilone, a combination thereof, a sions are natural compounds, synthetic compounds, semi synthetic analogue of a natural cannabinoid, as well
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