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WO 2018/187500 Al 11 October 2018 (11.10.2018) W !P O PCT

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WO 2018/187500 Al 11 October 2018 (11.10.2018) W !P O PCT (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date WO 2018/187500 Al 11 October 2018 (11.10.2018) W !P O PCT (51) International Patent Classification: WAN, Mohamed M.; 489 Alexa Drive, Oxford, MS 38655 A01H 6/28 (2018.01) G01N 30/02 (2006.01) (US). WANAS, Amira Samir; 218 Karen Drive, Oxford, G0 30/12 (2006.01) MS 38655 (US). (21) International Application Number: (74) Agent: RZUCIDLO, Eugene C ; Hershkovidz & A sso PCT/US20 18/026 126 ciates, PLLC, 2845 Duke Street, Alexandria, VA 22314 (US). (22) International Filing Date: 04 April 2018 (04.04.2018) (81) Designated States (unless otherwise indicated, for every kind of national protection available): AE, AG, AL, AM, (25) Filing Language: English AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, BZ, (26) Publication Language: English CA, CH, CL, CN, CO, CR, CU, CZ, DE, DJ, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, (30) Priority Data: HR, HU, ID, IL, IN, IR, IS, JO, JP, KE, KG, KH, KN, KP, 62/481,884 05 April 2017 (05.04.2017) US KR, KW, KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, (71) Applicant: UNIVERSITY OF MISSISSIPPI [US/US]; MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, 100 Barr Hall, University, MS 38677 (US). OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY,TH, TJ, TM, TN, (72) Inventors: ELSOHLY, Mahmoud A.; 708 Quiet Val TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. ley Cove, Oxford, MS 38655 (US). GUL, Wassem; 6205 Charleston Court Drive, Oxford, MS 38655 (US). RAD- (54) Title: ISOLATION OF PURE CANNABINOIDS FROM CANNABIS High CBD variety Cannabis plant Organic solvent or SCE Extract Heat l 30°C/30 Thin film distillation Distillate Decarboxylated Extract EtOH/Fi!ter Winterized Distillate t.boc-amino acid t.boc-amino acid Extract or distillate Derivative Si gel CC EtOAc/DCM (eluent) Impure CBD derivative Base Si gel CC Crystallization CBD crystals Pure CBD Figure 1 (57) Abstract: ∆ -Tetrahydrocannabinol (A -THC or THC) and cannabidiol (CBD) are major constituents of the Cannabis plant that have pharmacological properties with potential therapeutic value. This invention is directed to processes for large scale isolation of 00 these two and other cannabinoids from the Cannabis sativa plant. This is accomplished through the discovery that protected amino 00 acid esters of the cannabinoids are easier to separate using normal phase silica column chromatography. Mild base hydrolysis of the esters regenerates the free cannabinoids in a purified form. The invention is also applicable to the isolation of other cannabinoids from o Cannabis extracts. o [Continued on nextpage] WO 2018/187500 Al llll II II 11III II I I II I III I II II III II I II (84) Designated States (unless otherwise indicated, for every kind of regional protection available): ARIPO (BW, GH, GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, KM, ML, MR, NE, SN, TD, TG). Published: Title Isolation of pure cannabinoids from Cannabis Field of the Invention The present invention relates to the isolation of pure cannabinoids from Cannabis. Background of the Invention While delta-9-tetrahydrocannabinol ( 9-THC, 1) is the main biologically active component in the Cannabis sativa plant, and because the plant and its crude drug marijuana have been used (and abused), other cannabinoids such as cannabidiol (CBD, 2) have their own activities that promise utility in the treatment of many disease conditions. THC has been approved by the Food and Drug Administration (FDA) for the control of nausea and vomiting associated with chemotherapy and for appetite stimulation of AIDS patients suffering from the wasting syndrome. The drug, however, shows other biological activities which lend themselves to possible therapeutic applications, such as in the treatment of glaucoma ( 1 ) , migraine headaches (2, 3), spasticity (4), anxiety (5), and as an analgesic (4). It is because of these promising biological activities of THC that marijuana has been brought into medicinal use as a drug by many states in the USA despite the abuse potential of the drug and its illegal status on the federal level. One of the main points brought by the medicinal marijuana proponents is the fact that the currently available soft gelatin capsule formulation is very expensive and lacks consistency in its effects. The latter point could be explained since oral THC has erratic absorption from the gastrointestinal tract, is subject to the first-pass effect resulting in heavy metabolism with production of high levels of 11-OH-THC, and undesirable side effects. Another THC formulation which was proposed for development is a pro-drug consisting of THC hemisuccinate formulated in a suppository base (6). This formulation appeared to overcome all the problems associated with the oral preparation and has been shown to produce consistent bioavailability in animal studies (7). Preliminary clinical investigations showed promise for this formulation (8, 9 , 10). Regardless of which formulation is to be used for THC or a pro-drug thereof, a source for the active pharmaceutical ingredient is critical. The currently-marketed capsule formulation contains THC prepared by an expensive synthetic process. A more economical process is needed. Our research indicates that the process describe herein in which THC is isolated from the Cannabis plant material will be less expensive at the commercial scale than the s nthetic process. -THC (1) CBD (2) A second major phytocannabinoid, CBD (2), has attracted much attention for development as a pharmaceutical product for the treatment of several conditions because of its reported anxiolytic, anti-psychotic, antiemetic, anti-convulsant, and anti inflammatory properties ( 1 1- 13). Most notably it has been reported that a CBD extract ("CBD") oil may be effective in the treatment of intractable epilepsy in young children (Dravet Syndrome) (14). US Pat. No. 8,071 ,641 B2 describes the use of CBD to suppress diabetes and protect Langerhans islets from immunogenic destruction (insulitis) in NOD mice ( 1 5). Recently, Lannotti et al. (2014) evaluated the anticonvulsant effects of CBD and CBDV (Cannabidivarin) through TRPV1 channel activation and desensitization and in an in vitro model of epileptiform activity, and they concluded that CBD and CBDV dose- dependently activate and rapidly desensitize TRPV1 , as well as TRP channels of subfamily V type 2 (TRPV2) and subfamily A type 1 (TRPA1 ) , which could be a potential treatment for epilepsy (16). The application of CBD for the treatment of autoimmune hepatitis was patented by Nagarkatti et al. (2012). Both natural and synthetic CBD were tested, and the inventors claimed that CBD can trigger apoptosis in immune cells and act as anti- inflammatory/immuno-suppressive agent in treating hepatitis ( 1 7). Cannabinoid-containing plant extracts used as neuroprotective agents were studied by Guy and Piatt (2014), and it was found that both CBD and THC-containing plant extract reduced the concentration of intracellular calcium ions which could be of great potential as neuroprotective agents ( 1 8). Several investigations have been carried out over the years to isolate THC and CBD from the plant material, mostly to determine its chemical structure or to investigate the phytochemistry of the plant. The first isolation of the naturally-occurring THC in its pure form was reported by Gaoni and Mechoulam in 1964 ( 19). Delta-9-frans- tetrahydrocannabinol was isolated from the hexane extract of hashish by repeated column chromatography on florisil and alumina. Further purification was carried out by the preparation of the crystalline 3,5-dinitrophenylurethane of THC followed by mild basic hydrolysis to get the pure THC. The purity of THC was proven by thin layer chromatography (TLC) and spectroscopic analysis (IR and NMR). ElSohly and Ross reported a large-scale isolation and purification process for THC from the Cannabis plant material that involved extraction with a non-polar solvent, vacuum distillation of the extract and repeated chromatography of the distillate (20). Purification of the THC in the distillate reported by ElSohly and Ross was further investigated by J.R. Duchek (21 ) . A crystalline aryl sulfonyl derivative was prepared which upon repeated crystallization produced > 98% pure THC after base hydrolysis. Although the ElSohly and Ross method accomplished significant purification of THC from Cannabis, it involved chromatographic steps that required reversed phase silica High Performance Liquid Chromatography (HPLC) to provide significant purification and, in the meantime, low concentrations of other cannabinoids were found in the final product that would have made it difficult to meet the stringent regulatory requirements for active pharmaceutical ingredients. On the other hand, while the purification of THC by repeated crystallization of the tosylate ester (21 ) produced a pharmaceutical grade of THC, the yield was very low (approximately 25% recovery of the THC in the original extract). Therefore, a method is needed that could result in the isolation of THC from Cannabis that involves the use of normal phase chromatography and a final product of > 98% purity that meets the GMP requirements. THC produced by such a method from a natural source would offer an alternative to synthetic THC, which is not easily accessible, and will encourage the development of other (non-oral) formulations with better pharmacokinetic profiles that can bypass the first pass effect encountered by oral administration of THC and avoid the side effects associated with the oral product.
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