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Tommune Touchon Unutmaq Olmu TOMMUNE US009907823B1TOUCHONUNUTMAQ OLMU (12 ) United States Patent ( 10 ) Patent No. : US 9 , 907 ,823 B1 Kuhrts ( 45 ) Date of Patent: Mar. 6 , 2018 ( 54 ) WATER -SOLUBLE PHYTOCANNABINOID (58 ) Field of Classification Search FORMULATIONS CPC .. A61K 36 / 185 ; A61K 9 /0095 ; A61K 9 / 2013 ; A61K 9 /0014 ; A61K 9 / 0053 ; A61K (71 ) Applicant : Octarine Technologies LLC , Fairfield , 9 /4858 ; A61K 31 /05 ; A61K 9 /107 ; A23L CA (US ) 2 / 52 ; A23V 2002 / 00 See application file for complete search history . (72 ) Inventor : Eric Kuhrts , Fairfield , CA (US ) (56 ) References Cited (73 ) Assignee : Eric H . Kuhrts , Fairfield , CA (US ) U . S . PATENT DOCUMENTS ( * ) Notice : Subject to any disclaimer , the term of this 6 , 689 , 388 B2 2 / 2004 Kuhrts patent is extended or adjusted under 35 6 , 953 , 593 B2 10 / 2005 Kuhrts U . S . C . 154 ( b ) by 0 days. 8 , 071, 136 B2 12 / 2011 Kuhrts 8 , 349 ,375 B2 1 /2013 Kuhrts 8 , 883 , 225 B2 11 / 2014 Kuhrts ( 21 ) Appl. No. : 14 /791 , 181 2003 / 0228369 A1 12 / 2003 Kuhrts 2006 / 0068021 Al 3 / 2006 Kuhrts ( 22 ) Filed : Jul. 2 , 2015 2011/ 0054029 Al 3 / 2011 Kuhrts 2011 / 0281957 AL 11 / 2011 Kuhrts Related U . S . Application Data 2012 /0059052 Al 3 / 2012 Kuhrts 2013 / 0123368 A1 5 / 2013 Kuhrts ( 60 ) Provisional application No . 62/ 077, 153 , filed on Nov . 2013 /0245118 Al 9 /2013 Kuhrts 7 , 2014 . 2013 / 0287923 A1 10 /2013 Kuhrts 2014 /0235715 A1 8 / 2014 Kuhrts ( 51 ) Int. Ci. 2015 /0182625 A1 7 / 2015 Kuhrts A61K 36 / 185 ( 2006 .01 ) 2015 /0209307 A1 7 /2015 Kuhrts A61K 9 /00 ( 2006 .01 ) 2015 / 0224074 AL 8 / 2015 Kuhrts A23L 2 / 52 ( 2006 .01 ) 2015 /0290266 Al 10 /2015 Kuhrts A61K 9 / 20 ( 2006 .01 ) Primary Examiner — Trevor Love A61K 9 / 48 ( 2006 .01 ) ( 74 ) Attorney , Agent, or Firm — Thorpe North & Western A61K 31 /05 ( 2006 .01 ) LLP A61K 9 / 107 ( 2006 .01 ) ( 57 ) ABSTRACT A23L 1 / 30 ( 2006 .01 ) Methods and formulations for increasing the water solubility (52 ) U . S . CI. and /or bioavailability of a phytocannabinoid compound is CPC .. A61K 36 / 185 (2013 .01 ) ; A23L 1 /3002 (2013 .01 ) ; A23L 2 / 52 ( 2013. 01 ) ; A61K 9 /0014 disclosed herein . In one example , a water- soluble phytocan ( 2013 .01 ) ; A61K 9 /0053 ( 2013 .01 ) ; A61K nabinoid formulation can comprise a phytocannabinoid ; a 9 /0095 ( 2013 .01 ) ; A61K 9 / 107 ( 2013 .01 ) ; non - ionic surfactant; and optionally , water. The weight ratio A61K 9 / 2013 ( 2013 .01 ) ; A61K 9 /4858 of phytocannabinoid content to non - ionic surfactant can be (2013 .01 ) ; A61K 31/ 05 (2013 . 01 ) ; A23V from 1 : 10 , 000 to 1 : 5 . 2002/ 00 ( 2013 .01 ) 43 Claims, 2 Drawing Sheets Cannabidiol Blood Plasma Levels 2500 VAANANTWww 2000 Concentrationng/L Rat 1 + Rat 2 + Rat 3 * Mean 500 time( Hour 20 25 U . S . Patent Mar. 6 , 2018 Sheet 1 of 2 US 9 , 907 ,823 B1 Eie WIWIAMINIWAN Lied zey-+ U?w-* WUUS TELESNAISIIHELNIENISRIIDILI branscomm MerrrrrrrrrowwwwwwwwwwwvWWW.NNNNN28AnwerrromwWo VIRU MANINIMAAHAN M unasom.mmmmáron WNAWIAMONrrerawan ANJJJANAMILANSINNIWINNAA 1BIJ s??????sejapoolajoi?iq????? MWANZA mwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwww MUAJAJJJMUAARIMIZA SISTERJIITTEISESEISESTARANISRIIPLIII111NTERVISESPERIFREEFLEIERENISSEHEESECAKSIE Narreren www wwwwwwwwwwwyourm mumkwww. w MWwwwwwwwwPWANAJWIJNNUVAWNWNIDAVA 16 Wrism TRX inn wwww 009 009Z 0007 l/ ng Concentration U . S . Patent Mar. 6 , 2018 Sheet 2 of 2 US 9 ,907 , 823 B1 Trrrrrrrrrrrr ????????????????????????????? rrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrr 27727 rrrrrrrrr 1111111111111111111111111111 uodejnujos10!pqeuueyalgniosvarem 11111111111111 rrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrr rrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrr ????????? rrrrrrrrrrrrrrrrrrrrrrrrrr 11111111111 recerererererer 1111111111/111111111777777777 corno jew?uejad?sopSuos corerna 2012 (sunoyvz)uogdiosqujo!puue)jetoj 111111111111111111111111111111111111111111111111111111111111111111111111111111111101111111111111111111111111111111111111111111111111111111 rrurerend 21777212112121227 77111111111111111111 rrrrrrrrrcccdcrca JJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJUNNIWINUWIIIIIIII ??!0qeau??[q?ll?????????????? 201211777777777777777777777777777 narroccorrrrrrrrrrrrrrrrrrr rrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrr IIIIIIIIIIIIIIIIIIIIIIIWW. 211111111000011111111n 1111111111111111111111111111111111unnerrrrrrrrrrrrrrr rrrrrrrr ° 1111111111111111111111111111111111111111111111111111111111111111111111111111111101111111111111111111111111111111111110111111 )mg / mL / ng .kg - hr( AUCO US 9 , 907 , 823 B1 WATER - SOLUBLE PHYTOCANNABINOID Alterations and further modifications of the inventive fea FORMULATIONS tures illustrated herein , and additional applications of the principles of the disclosure as illustrated herein , which The present application claims the benefit of U . S . Provi would occur to one skilled in the relevant art and having sional Patent Application No . 62 /077 , 153 , which was filed 5 possession of this disclosure , are to be considered within the on Nov. 7 , 2014 , the entirety of which is incorporated herein scope of the disclosure . It is also to be understood that this by reference . disclosure is not limited to the particular configurations , process steps and materials disclosed herein , as these may BACKGROUND vary to some degree . Further , it is to be understood that the 10 terminology used herein is used for the purpose of describ Hemp is an industrial plant that can be grown on a large ing particular embodiments only , and is not intended to be scale in many regions of the world . Hemp, also known as limiting as the scope of the present disclosure. cannabis , has a long history of use in humans as an The singular forms “ a ," " an , ” and “ the” include plural anticonvulsant, sedative , hypnotic , anti - depressant, analge - referents unless the context clearly dictates otherwise . Thus , sic , anti - inflammatory , anti -emetic , anti - spasmodic , and 15 for example, reference to “ a non - ionic surfactant” includes appetite - stimulator. Cannabis contains a broad spectrum of reference to one or more of such non - ionic surfactants . chemical compounds including : phytocannabinoids , terpe The formulations described herein can be used in the noids ( essential oils ) , flavonoids, enzymes, and steroids. context of " combination therapy ” or “ adjunct therapy ” with While delta - 9 - tetrahydrocannabinol ( delta - 9 - THC ) is other drugs to treat or otherwise provide a benefit with believed to be the principle psychoactive component of 20 respect to a disease or other malady . This combination hemp, other phytocannabinoids ( such as cannabidiol, can therapy can be sequential therapy where the patient is treated nabinol, and cannabichromene ) are thought to possess first with one drug and then the other or the two drugs are numerous medicinal properties without the psychoactive given simultaneously . The present disclosure includes com effects of delta - 9 - THC . However , the oral bioavailability of bination therapy or adjunct therapy using the water soluble these phytocannabinoids is limited . For example , the oral 25 formulations of the present disclosure . bioavailability of cannabidiol was found to be about 6 % . As used herein , the term “ clear ” is intended to relate to a The limited bioavailability of these phytocannabinoids is solution or aqueous solution containing the natural lipo believed to be because cannabidiol is a natural fat soluble philic compound in a water containing solution ( e . g . a compound that is hydrophobic and thus insoluble in water. beverage ) that is free of visible particles of undissolved Due to the many desirable properties of phytocannabinoids, 30 compound . A clear solution or clear aqueous solution such as cannabidiol, it would be advantageous to provide includes both solutions as well as very fine dispersions that improved , stable , water soluble formulations, with enhanced remain clear upon sitting undisturbed for one hour or more . bioavailability for human consumption in various conve Essentially no visible ( to the naked eye ) particles or micelles nient formulations such as juices , soft drinks , bottled water , are present. When the clear aqueous solution is a beverage , 35 the clear aqueous solution may sometimes not need to be and liquid concentrates . shaken prior to consuming . BRIEF DESCRIPTION OF THE DRAWINGS A " non - alcoholic ” formulation , as used herein , is a for mulation that does not include or includes only de minimis Features and advantages of the technology disclosed or trace amounts of methanol, ethanol, propanol or butanol. herein will be apparent from the detailed description that 40 The term “ non - aprotic solvated , ” as used herein , means follows, taken in conjunction with the accompanying figures that water soluble aprotic solvents are absent or are included that together illustrate features of the technology . It is only in de minimis or trace amounts. understood that these figures merely depict exemplary “ Nutraceutical ” includes lipophilic compounds or essen embodiments and are not, therefore , to be considered lim - tial oils derived from natural sources such as cannabis , iting in scope . Furthermore , it will be readily appreciated 45 blueberries, grapes, other berries , soybeans, cocoa beans , that the components , as generally described and illustrated tomatoes , green tea , turmeric , citrus fruit , other botanical in the figures herein , could be arranged and designed in a sources, compounds produced
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