THOM US010080736B2TULLITTUR (12 ) United States Patent ( 10 ) Patent No. : US 10 ,080 , 736 B2 Kleidon et al. (45 ) Date of Patent: Sep . 25 , 2018 ( 54 ) MICROENCAPSULATED CANNABINOID ( 58 ) Field of Classification Search COMPOSITIONS CPC . .. A61K 31/ 352 ; A23L 33/ 115 ; A23D 7 / 001 ; A23D 9 / 00 (71 ) Applicant: Ojai Energetics PBC , Ojai, CA (US ) See application file for complete search history. ( 72 ) Inventors : William Kleidon , Ojai, CA (US ) ; Justin Kirkland , Champaign , IL (US ) ( 56 ) References Cited ( 73 ) Assignee : OJAI ENERGETICS PBC , Ojai, CA U . S . PATENT DOCUMENTS ( US ) 3 ,456 ,049 A 7 / 1969 Edward et al . ( * ) Notice : Subject to any disclaimer , the term of this 4 ,888 , 194 A * 12/ 1989 Andersen . .. .. .. A23C 13 /12 patent is extended or adjusted under 35 426 / 570 U . S . C . 154 (b ) by 0 days . ( Continued ) (21 ) Appl. No. : 15 / 452 ,530 FOREIGN PATENT DOCUMENTS WO WO - 9843497 A2 10 / 1998 ( 22 ) Filed : Mar. 7 , 2017 WO W O - 2012075575 A1 6 / 2012 (Continued ) (65 ) Prior Publication Data US 2017/ 0172977 A1 Jun . 22 , 2017 OTHER PUBLICATIONS Related U . S . Application Data Afoulous, et al . Helichrysum gymnocephalum essential oil: chemi cal composition and cytotoxic , antimalarial and antioxidant activi (63 ) Continuation of application No . ties , attribution of the activity origin by correlations. Molecules . PCT/ US2015 / 065268 , filed on Dec . 11 , 2015 . Sep . 29 , 2011; 16 ( 10 ) : 8273 -91 . doi: 10 .3390 /molecules 16108273 . (Continued ) (Continued ) (51 ) Int. Cl. A61K 31 / 352 (2006 . 01) Primary Examiner — Jianfeng Song A61K 31 /05 ( 2006 .01 ) ( 74 ) Attorney , Agent, or Firm — Wilson Sonsini Goodrich (Continued ) Rosati (52 ) U . S. CI. CPC . .. .. .. .. .. A61K 31/ 352 (2013 . 01 ) ; A23D 77001 (2013 .01 ) ; A23D 9 / 00 (2013 .01 ) ; A23G 9 /52 (57 ) ABSTRACT ( 2013 .01 ) ; A23L 2 /52 ( 2013 .01 ) ; A23L 29 /256 The present invention relates to cannabinoid compositions. (2016 .08 ) ; A23L 33 / 105 (2016 .08 ) ; A23L These compositions can be encapsulated ( e . g ., microencap 33 / 115 ( 2016 .08 ) ; A61K 8 / 068 ( 2013 .01 ) ; sulated ) . In particular, these compositions can be adminis A61K 8 / 347 ( 2013 .01 ) ; A61K 8 /498 ( 2013 .01 ) ; tered to a subject , such as through oral consumption or A61K 8 / 733 ( 2013 .01 ) ; A61K 8 / 922 (2013 . 01) ; topical treatment. A61K 9 /0095 ( 2013 .01 ) ; A61K 9 / 1075 ( 2013 . 01) ; (Continued ) 16 Claims, 9 Drawing Sheets US 10 ,080 , 736 B2 Page 2 Related U . S . Application Data OTHER PUBLICATIONS (60 ) Provisional application No . 62 /091 , 445 , filed on Dec. 12 , 2014 , provisional application No. 62 / 128 , 761, Ahmad , et al. Preclinical renal cancer chemopreventive efficacy of filed on Mar. 5 , 2015 . geraniol by modulation of multiple molecular pathways . Toxicol ogy . Nov. 28 , 2011 ;290 ( 1 ) :69 - 81. doi: 10 . 1016 / j. tox . 2011 .08 . 020 . (51 ) Int . CI. Epub Sep . 3 , 2011. A61K 9 /50 ( 2006 .01 ) Ahmed , et al . Phytochemical Analysis and Anti - cancer Investiga A61K 36 / 185 ( 2006 . 01 ) tion of Bswellia serrata Bioactive Constituents In Vitro . Asian Pac A61K 31 /57 ( 2006 .01 ) J Cancer Prev . 2015 ; 16 ( 16 ) :7179 - 88 . A610 19 / 00 ( 2006 .01 ) Ali , et al. Chemical composition , antimicrobial, antioxidant and cytotoxic activity of essential oils of Plectranthus cylindraceus and A23D 7700 ( 2006 . 01 ) Meriandra benghalensis from Yemen . Nat Prod Commun . Aug . A23L 33 / 115 ( 2016 . 01 ) 2012 ; 7 ( 8 ) : 1099 - 102 . A23G 9 /52 ( 2006 .01 ) Alizadeh , et al . Essential oil composition , phenolic content, anti A61K 45 / 06 ( 2006 .01 ) oxidant, and antimicrobial activity of cultivated Satureja rechingeri A61K 31 /015 ( 2006 .01 ) Jamzad at different phenological stages. Z Naturforsch C . 2015 ;70 ( 3 A61K 31 /045 ( 2006 .01 ) 4 ) : 51 - 8 . doi: 10 . 1515 /znc -2014 -4121 . A6IK 31/ 192 ( 2006 .01 ) Alonso , et al. Acclimation mechanisms elicited by sprayed abscisic A23L 2 /52 ( 2006 . 01 ) acid , solar UV - B and water deficit in leaf tissues of field - grown A23L 29 / 256 ( 2016 . 01 ) grapevines. Plant Physiol Biochem . Jun . 2015 ;91 : 56 -60 . doi: 10 . 1016 / A23L 33 / 105 ( 2016 .01 ) j. plaphy .2015 .03 .011 . Epub Apr . 8 , 2015 . A61K 9 / 00 ( 2006 .01 ) Anter, et al. Antigenotoxicity , cytotoxicity , and apoptosis induction A23D 9 /00 ( 2006 .01 ) by apigenin , bisabolol, and protocatechuic acid . J Med Food . Mar. A61K 8 / 06 ( 2006 .01 ) 2011 ; 14 ( 3 ) :276 - 83 . doi: 10 . 1089 / jmf. 2010 .0139 . Epub Dec . 23 , A61K 8 / 34 ( 2006 .01 ) 2010 . A61K 8 / 49 ( 2006 .01 ) Armaka, et al . Antiviral properties of isoborneol, a potent inhibitor A61K 8 / 73 ( 2006 .01 ) of herpes simplex virus type 1 . Antiviral Res . Sep . 1999 ; 43 ( 2 ) : 79 A61K 8 / 92 ( 2006 .01 ) 92 . A61K 9 / 107 ( 2006 .01 ) Athikomkulchai, et al . Chemical Composition of the Essential Oil from Croton oblongifolius and its Antibacterial Activity against (52 ) U . S . CI. Propionibacterium acnes . Nat Prod Commun . Aug . 2015 ; 10 ( 8 ) : 1459 ??? . .. A61K 9 / 5036 ( 2013 . 01 ) ; A61K 31 /015 60 . ( 2013 .01 ) ; A61K 31/ 045 (2013 .01 ) ; A61K Aydin , et al. Anticancer and antioxidant properties of terpinolene in 31/ 05 ( 2013 .01 ) ; A61K 31/ 192 ( 2013 .01 ) ; rat brain cells . Arh Hig Rada Toksikol. Sep . 2013 ;64 ( 3 ) :415 - 24 . doi : A61K 31/ 57 ( 2013 . 01 ) ; A61K 36 / 185 10 .2478 / 10004 - 1254 -64 - 2013 - 2365 . ( 2013 . 01 ) ; A61K 45 / 06 (2013 .01 ) ; A61Q Barbieri, et al. Antioxidant activity and chemical composition of 19/ 007 ( 2013 .01 ) ; A23V 2002 /00 ( 2013 .01 ) essential oils of three aromatic plants from La Rioja province . Pharm Biol. Apr. 13 , 2015 : 1 - 6 . [ Epub ahead of print ]. ( 56 ) References Cited Bedse, et al . The role of endocannabinoid signaling in the molecular mechanisms of neurodegeneration in Alzheimer ' s disease . J Alzheimers U . S . PATENT DOCUMENTS Dis . 2015 ; 43 ( 4 ) : 1115 - 36 . doi: 10 . 3233 / JAD - 141635 . Ben Ali , et al . Investigation of Antiulcer and Antioxidant Activity of 5 ,674 ,522 A 10 / 1997 Shah et al. Juniperus phoenicea L . ( 1753 ) Essential Oil in an Experimental Rat 7 , 399 , 872 B27 / 2008 Webster et al. Model . Biol Pharm Bull . 2015 ;38 ( 11) : 1738 -46 . doi: 10 . 1248 / bpb . 8 , 808 , 734 B2 8 / 2014 Winnicki b15 - 00412 . 9 ,095 ,555 B2 8 / 2015 Winnicki Bomfim , et al . Antitumour Activity of the Microencapsulation of 2004 /0132621 A1 * 7 / 2004 Frisch .. .. .. .. .. .. AOIN 25 /04 504 / 363 Annona vepretorum Essential Oil. Basic Clin Pharmacol Toxicol . 2006 / 0051416 AL 3 / 2006 Rastogi et al . Sep . 8 , 2015 . doi: 10 . 1111/ bcpt . 12488 . [Epub ahead of print] . 2006 /0269606 AL 11/ 2006 Gustafsson et al . Bonamin , et al. The effect of a minor constituent of essential oil 2007 /0065512 A1 3 / 2007 Dedhiya et al. from Citrus aurantium : the role of B -myrcene in preventing peptic 2007 /0298100 Al 12 / 2007 Barras et al. ulcer disease . Chem Biol Interact . Apr . 5 , 2014 ;212 : 11 - 9 . doi: 2008/ 0242741 Al 10 / 2008 Perry 10 . 1016 / j .cbi . 2014 .01 .009 . Epub Jan . 27 , 2014 . 2008/ 0279940 AL 11/ 2008 Rigassi et al. Bonifacio , et al . a -bisabolol is an effective proapoptotic agent 2009 /0110674 AL 4 /2009 Loizou against BCR - ABL ( + ) cells in synergism with Imatinib and Nilotinib . 2011/ 0086829 A1 * 4 / 2011 Zadini . .. .. .. A61K 31/ 575 PLoS One. 2012 ; 7 ( 10 ): e46674 . doi: 10 . 1371 /journal . pone . 0046674 . 514 / 182 Epub Oct. 3 , 2012 . 2011/ 0236364 A1 * 9 /2011 Bromley . A23L 2 /52 Bouajaj , et al . Antibacterial , allelopathic and antioxidant activities of 424 / 94 . 1 2012 / 0043242 AL 2 /2012 Hospodor essential oil of Salvia officinalis L . growing wild in the Atlas 2012 / 0046351 A1 2 /2012 Hospodor Mountains of Morocco . Nat Prod Res . 2013 ; 27 ( 18 ): 1673 - 6 . doi : 2012 / 0046352 Al 2 /2012 Hospodor 10 . 1080 / 14786419. 2012. 751600 . Epub Dec. 14 , 2012 . 2012 /0095088 Al 4 / 2012 Hospodor Boukhatem , et al. Rose geranium essential oil as a source of new 2012 /0231083 A1 9 / 2012 Carley et al . and safe anti - inflammatory drugs . Libyan JMed . Oct. 7 , 2013 ; 8 : 22520 . 2013 /0089600 A1 4 / 2013 Winnicki doi: 10 .3402 / ljm . v8i0 . 22520 . 2016 / 0089320 A1 3 / 2016 Tan Bounihi, et al. In Vivo Potential Anti- Inflammatory Activity of Melissa officinalis L . Essential Oil . Adv Pharmacol Sci . FOREIGN PATENT DOCUMENTS 2013; 2013 : 101759 . doi: 10 . 1155 / 2013 / 101759 . Epub Dec . 5 , 2013 . Cao , et al . The potential therapeutic effects of THC on Alzheimer ' s WO WO - 2013108254 AL 7 / 2013 disease . J Alzheimers Dis . 2014 ; 42 ( 3 ) : 973 - 84 . doi: 10 .3233 / JAD WO WO2014100231 * 4 /2014 140093 . WO WO - 2014100231 Al 6 / 2014 Carter , et al. Cannabis and amyotrophic lateral sclerosis : hypotheti WO WO - 2014134281 A1 9 / 2014 cal and practical applications, and a call for clinical trials . Am J US 10 ,080 ,736 B2 Page 3 ( 56 ) References Cited displays antitumor activity in vivo . Biochem Biophys Res Commun . Nov . 27 , 2015 ; 467 ( 4 ) :928 -34 . doi : 10 . 1016 / j .bbrc .2015 . 10 . 041 . Epub OTHER PUBLICATIONS Oct . 16 , 2015 . Goulart , et al . Terpenes arrest parasite development and inhibit Hosp Palliat Care . Aug . 2010 ; 27 ( 5 ) : 347 - 56 . doi: 10 . 1177 / biosynthesis of isoprenoids in Plasmodium falciparum . Antimicrob 1049909110369531. Epub May 3 , 2010 . Agents Chemother . Jul. 2004 ; 48 ( 7 ) : 2502 - 9 . Cavalieri, et al. Pro - apoptotic activity of a -bisabolol in preclinical Guleria , et al . Antioxidant and antimicrobial properties of the models of primary human acute leukemia cells . J Transl Med . Apr. essential oil and extracts of Zanthoxylum alatum grown in north 21 , 2011; 9 :45 . doi: 10 . 1186 / 1479 - 5876 - 9 - 45 . western Himalaya . Scientific WorldJournal .May 28 , 2013 ;2013 :790580 . Chen , et al. Effect of Hinoki and Meniki Essential Oils on Human Autonomic Nervous System Activity and Mood States . Nat Prod doi: 10 . 1155 / 2013 / 790580 . Print 2013 . Commun . Jul. 2015 ; 10 ( 7 ) : 1 305 - 8 .