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The Two Tonttitulu Willkommune THETWO TONTTITULUUS 20170232210A1 WILLKOMMUNE ( 19) United States (12 ) Patent Application Publication (10 ) Pub. No. : US 2017/ 0232210 A1 Boeckl et al. ( 43 ) Pub . Date : Aug . 17 , 2017 ( 54 ) ENCAPSULATION OF LIPOPHILIC Publication Classification INGREDIENTS IN DISPENSIBLE SPRAY (51 ) Int. CI. DRIED POWDERS SUITABLE FOR A61M 11/ 02 ( 2006 .01 ) INHALATION AGIM 15 / 00 ( 2006 .01 ) A61K 9 / 00 ( 2006 . 01) ( 71) Applicant : Flurry Powders, Tarpon Springs , FL B01J 13 /04 ( 2006 . 01 ) (US ) A61K 9 / 14 ( 2006 .01 ) (52 ) U . S . CI. (72 ) Inventors : Andrew John Boeckl , Tarpon Springs, CPC .. .. .. A61M 11 /02 ( 2013 .01 ) ; BOIJ 13 /043 FL (US ) ; David Edward Cookson , (2013 .01 ) ; A61K 9 / 14 ( 2013 . 01 ) ; A61K 9 /0075 Orlando , FL ( US ) (2013 .01 ) ; A61M 15 / 00 ( 2013 .01 ) ; A61M 2202/ 064 (2013 . 01) (57 ) ABSTRACT ( 21 ) Appl. No. : 15 /411 , 753 A method of manufacturing a flowable and dispersible powder includes solubilizing a lipophilic substance in a terpene to form a mixture and treating the mixture to form 8(22 ) Filed : Jan . 20 , 2017 a nanoemulsion dispersed in an aqueous solution . The aqueous solution includes at least one functional excipient. The nanoemulsion is then spray dried , thereby evaporating Related U . S . Application Data first the aqueous portion and then the terpene to form a dry 8(60 ) Provisional application No . 62 /280 , 968, filed on Jan . powder formed from solid particles comprising the lipo 20 , 2016 . philic substance . Patent Application Publication Aug. 17 , 2017 Sheet 1 of 8 US 2017 / 0232210 A1 102 SOLUBILIZE A LIPOPHILIC SUBSTANCE IN A TERPENE OR OTHER ORGANIC SOLVENT TO FORMA MIXTURE 104 ADD AT LEAST ONE FUNCTIONAL EXCIPIENT TO WATER TO FORM AN AQUEOUS SOLUTION DISPERSE THE MIXTURE INTO THE AQUEOUS 106 SOLUTION USING A HOMOGENIZER OR ULTRASONIC DEVICE TO FORM A COARSE EMULSION TREAT THE COURSE EMULSION WITH AN ULTRASONIC OR HIGH SHEAR DEVICE TO FORM AN EMULSION WITH NANOSIZED OIL PARTICLES SPRAY DRY THE AQUEOUS SOLUTION , THEREBY 110 EVAPORATING THE TERPENE AND AN AQUEOUS PORTION OF THE AQUEOUS SOLUTION TO FORMA DRY POWDER FORMED FROM SOLID PARTICLES THAT INCLUDE THE LIPOPHILIC SUBSTANCE FIG . 1 100 Patent Application Publication Aug. 17 , 2017 Sheet 2 of 8 US 2017 / 0232210 A1 202 DISSOLVE A LIPOPHILIC INGREDIENT IN AN ORGANIC SOLVENT TO FORM A LIPOPHILIC PHASE 204 DISSOLVE A SURFACTANT AND / OR EMULSIFIER IN THE LIPOPHILIC PHASE 206 DISSOLVE ONE OR MORE EXCIPIENTS INTO WATER TO FORM AN AQUEOUS PHASE DISPERSE THE LIPOPHILIC PHASE INTO THE 208 AQUEOUS PHASE TO FORM AN EMULSION THAT INCLUDES NANOSIZED OIL DROPLETS SPRAY DRY THE EMULSION TO FORM A DRY 210 POWDER THAT INCLUDES THE LIPOPHILIC INGREDIENT FIG . 2 200 Patent Application Publication Aug. 17 , 2017 Sheet 3 of 8 US 2017 / 0232210 A1 302 MIX AN OIL SOLUTION WITH A WATER SOLUTION TO FORM AN OIL - IN -WATER EMULSION COMPOSITION 304 SPRAY DRY THE OIL - IN -WATER EMULSION TO FORM A DRY POWDER COMPOSITION FIGW . 3 300 Patent Application Publication Aug. 17 , 2017 Sheet 4 of 8 US 2017 / 0232210 A1 404 PartB.001-3nmoildroplets 2 OPartA.aqueousphase - . *** * * ** : 1: 11 ? . ? . FIG.4 .. n . ir > 400 402 Patent Application Publication Aug. 17 , 2017 Sheet 5 of 8 US 2017 / 0232210 A1 VolumeDensity(9) W are 10obotohet. 01 t e 10 . 0 Size Classes cum Sample Name Dx ( 10 ) Cum ) Dx (50 ) ( un ) Dx (90 ) ( jum ) F20170104 _ 1 MAC 14K 2 0944 0268 0 .505 FIG . 5 Patent Application Publication Aug. 17 , 2017 Sheet 6 of 8 US 2017 / 0232210 A1 ????????????ity” .. 3 II TOITEET MITTIMETI 920 .01 1. 0 100 100 . 0 1, 000, 0 10, 0000 Size Classes (um ) Sample Name Dx (10 m ) Dx (50 ) kum Dx ( 90 ) um . P20150828 -29 0 .872 464 . * * . * * . * * . * * . * * . * * . * Ver P20150826 - 3 rrrrrrrrrrrrrrrrrr rrrrrrrrrrrrrrrrrrr FIG . 6 Patent Application Publication Aug. 17 , 2017 Sheet 7 of 8 US 2017 / 0232210 A1 1230SEI 5pm FIG.7 X5,000 10KV Patent Application Publication Aug. 17 , 2017 Sheet 8 of 8 US 2017 / 0232210 A1 VolumeDensitya W * *** * * * Angelica TTTTY 22is ME & TTITIE TTE : 41111 0 . 01 0 . 1 1 . 0 10 . 0 100 . 0 1 ,000 , 0 10 ,0000 Size Classes (un ) Sample Name Dx ( 10 ) (fam . Dx (50 ) (PTI Dx (903 ) ( m ) * * * P20150511 - 3 111 2 . 24 4 .24 FIG . 8 US 2017 /0232210 A1 Aug . 17 , 2017 ENCAPSULATION OF LIPOPHILIC in the oil fraction that is spray dried to form a dry powder INGREDIENTS IN DISPENSIBLE SPRAY composition . The oil - in -water emulsion compositions may DRIED POWDERS SUITABLE FOR include a hydrophobic amino acid , e . g . leucine , a disaccha INHALATION ride , e . g . trehalose , and / or an oligosaccharide , e . g . inulin . Such dry powder compositions may be administered to a CROSS - REFERENCE TO RELATED subject via pulmonary inhalation . APPLICATIONS [ 0005 ] In one aspect , a method of manufacturing a flow [ 0001] This application is a non -provisional of U . S . Pro able and dispersible powder is provided . The method may visional Application No . 62 /280 , 968, filed on Jan . 20 , 2016 , include solubilizing a lipophilic substance in a terpene to form a mixture and treating the mixture to form a nanoe the complete disclosure of which is herein incorporated by mulsion dispersed in an aqueous solution . The aqueous reference . solution may include at least one functional excipient. The terpene fraction may include at least one functional excipi BACKGROUND OF THE INVENTION ent. The method may also include spraying drying the [0002 ] Due to their hydrophobic nature and low solubility nanoemulsion , thereby evaporating at least a portion of the in water , lipophilic active substances often exhibit poor terpene and the majority of the water to form a suitable dry bioavailability via the oral gastrointestinal (GI ) delivery powder formed from solid particles that include the lipo route . Furthermore , accurate and precise dosing is poor for philic substance . drugs delivered via the GI system due to inherent variability [0006 ] In another aspect , a method of manufacturing a caused by factors such as fasting state and first pass metabo flowable and dispersible powder includes dissolving a lipo lism . As an alternative , pulmonary delivery using a dry philic ingredient in an organic solvent to form a lipophilic powder inhaler (DPI ) may be used . Traditional lactose phase and dissolving at least one of a surfactant or an carrier (lactose blend ) formulations for DPIs typically offer emulsifier in the lipophilic phase . The method may also low drug loads , commonly less than 6 % (wt / wt ) , and low include dissolving one or more excipients into water to form delivery efficiencies (DE ) , typically delivering < 30 % of the an aqueous phase and chilling the aqueous phase to between drug to the lungs . Lactose blends are also highly flow rate about 1° C . and 10° C . The method may further include dependent, showing significant variability with respect to dispersing the lipophilic phase into the chilled aqueous aerodynamic performance . Once formulated , lactose blends phase to form an emulsion that includes nanosized oil rely on inter -particle forces to bind micronized drug to larger droplets . Alternatively , the emulsion may be prepared by lactose carrier particles to maintain a uniform distribution of heating the organic and aqueous phases to between 50 and drug . This can present challenges during transportation and 75° C . The method may include spray drying the emulsion filling of powder into packages, which impart mechanical to form a dry powder that includes one or more lipophilic energy capable of redistributing or otherwise disturbing ingredients . blend uniformity . [0007 ] In another aspect, a method of manufacturing a [ 0003 ] Engineered particles ( e . g . spray dried ) for DPIS flowable and dispersible powder may include mixing an oil offer significant improvements in drug payload , DE , good solution with a water solution to form an oil - in - water aerosol performance across a wide flow rates, and a lower emulsion composition . The oil solution may include a can risk for segregation of drug from excipients . However, nabinoid . The method may also include spray drying the lipophilic drug substances are challenging to encapsulate oil -in -water emulsion composition to form a dry powder into dry , flowable , and dispersible powders that are compat composition . ible with dry powder inhalers . In addition , oils and fats [0008 ] In another aspect, a dry powder composition is exhibit poor dissolution and dispersion when incorporated provided . The dry powder composition may include a lipo into aqueous systems which are common in the preparation philic component and one or more of a hydrophobic amino of annex solutions used to produce spray dried powders . acid , a disaccharide, a oligosaccharide, a surfactant, an This invention relates to new uses for terpenes as non - toxic , emulsifier, a stabilizing additive , or a bulking agent. The dry natural solubilizers for preparing vehicles ( or annex solu powder composition may have bulk density between 0 . 05 tions ) which may then be spray dried to produce powders and 0 . 30 g / cm ” , tap density between 0 . 10 and 0 .60 g / cm ” , comprising various drugs , agricultural chemicals , cosmetics , and moisture content below about 10 % w / w . The dry powder and foods. composition may also include between about 0 .01 % and 60 % w / w of the lipophilic component. BRIEF SUMMARY OF THE INVENTION [0009 ] In another aspect, a method of aerosolizing a dry [0004 ] The present disclosure generally relates to dry powder formulation is provided . The method may include powder compositions and methods for administering and providing a dry powder formulation that has a lipophilic preparing such compositions . Embodiments are directed to component and one or more of a hydrophobic amino acid , a dry powder compositions in which volatile terpenes are used disaccharide , a oligosaccharide , a surfactant, an emulsifier, a as processing aids to create nanoemulsions containing lipo stabilizing additive , or a bulking agent. The dry powder philic active substances , which may then be stabilized in dry composition may include between about 0 .01 % and 50 % powder form , and to methods for preparing and using such w / w of the lipophilic component.
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