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WO 2011/094219 Al (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 , « i ... .. .. 4 August 2011 (04.08.2011) WO 2011/094219 Al (51) International Patent Classification: (81) Designated States (unless otherwise indicated, for every A01N 25/30 (2006.01) A01N 25/22 (2006.01) kind of national protection available): AE, AG, AL, AM, A 25/26 (2006.01) A01C 1/06 (2006.01) AO, AT, AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, DO, (21) International Application Number: DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, PCT/US201 1/022439 HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, (22) International Filing Date: KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, 25 January 20 11 (25 .0 1.20 11) ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PE, PG, PH, PL, PT, RO, RS, RU, SC, SD, (25) Filing Language: English SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, (26) Publication Language: English TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (30) Priority Data: (84) Designated States (unless otherwise indicated, for every 61/298,532 26 January 2010 (26.01 .2010) US kind of regional protection available): ARIPO (BW, GH, 61/321,966 8 April 2010 (08.04.2010) US GM, KE, LR, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, MD, RU, TJ, (72) Inventor; and TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, (71) Applicant : KROON, Hendrick-Andre [NL/US]; 24 EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, Sylvan Road North, Westport, Connecticut 06880 (US). 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, (72) Inventors; and GW, ML, MR, NE, SN, TD, TG). (75) Inventors/ Applicants (for US only): HENRY, William [GB/GB]; No. 1 Kemps Piece, High Street, Haddenham Published: Buckinghamshire HP178LA (GB). EVANS-FREKE, — with international search report (Art. 21(3)) Stephen [IE/US]; P.O. Box 270, St. Thomas, 00804 (VI). — before the expiration of the time limit for amending the (74) Agent: REITER, Stephen E.; Foley & Lardner LLP, claims and to be republished in the event of receipt of 3579 Valley Centre Drive, Suite 300, San Diego, Califor amendments (Rule 48.2(h)) nia 92130 (US). < © (54) Title: VESICULAR FORMULATIONS (57) Abstract: Disclosed herein are vesicular formulations that include one or more phospholipids and one or more surfactants. In certain embodiments the use of such formulations are for the delivery of fatty acids for the treatment of disorders such as, fatty acid metabolic disorders, including essential fatty acid deficiency; pain or inflammation or osteoarthritis. In certain embodiments ¾ the use of such formulations are for use in agriculture, for example for applying agents to plants and crops intended for human consumption. VESICULAR FORMULATIONS [0001] This application claims the benefit of U.S. Provisional Patent Application No. 61/298,532, entitled "Vesicular Formulations," filed January 26, 2010 and U.S. Provisional Patent Application No. 61/321,966, entitled "Vesicular Formulations," filed April 8, 2010, each of which are hereby incorporated by reference in their entirety for all purposes. 1. FIELD OF INVENTION [0002] Provided herein are compositions and methods relating to formulations of phospholipids and surfactants. Certain aspects and embodiments relate to methods of using such formulations, including agricultural methods. 2. BACKGROUND [0003] U.S. Patent No. 6,165,500 to Cevc describes a "preparation for the application of agents . provided with membrane-like structures consisting of one or several layers of amphiphilic molecules, or an amphiphilic carrier substance, in particular for transporting the agent into and through natural barriers such as skin and similar materials." Abstract. These transfersomes "consist of one or several components[, m]ost commonly a mixture of basic substances, one or several edge-active substances, and agents []." Col. 5, lines 28-30. According to U.S. Patent No. 6,165,500, "[l]ipids and other amphiphiles are best suited basic substances; surfactants or suitable solvents are the best choice from the point of view of edge- active substances[, and a]ll of these can be mixed with agents in certain proportions depending both on the choice of the starting substances and on their absolute concentration." Col. 5, lines 30-35. [0004] U.S. Patent Application Publication No. US 2004/0071767 to Cevc et al. describes "formulations of nonsteroidal anti-inflammatory drugs (NSAIDs) based on complex aggregates with at least three amphiphatic components suspended in a . pharmaceutically acceptable . medium." Abstract. "One of these components is capable of forming stable, large bilayer membranes on its own. The other at least two amphiphatic components, including an NSAID, tend to destabilise such membranes." Paragraph [0002]. [0005] U.S. Patent Application Publication No. US 2004/0105881 to Cevc et al. describes extended surface aggregates, "suspendable in a suitable liquid medium and comprising at least three amphiphats (amphiphatic components) and being capable to improve the transport of actives through semi-permeable barriers, such as the skin, especially for the non-invasive drug application in vivo by means of barrier penetration by such aggregates." Paragraph [0002]. "The three amphiphats include at least one membrane forming compound (MFC), which can form the membrane of [the aggregates], and at least two membrane destabilising compounds (MDCi and MDC2) differentiated by their capability of forming smaller aggregates (with no extended surfaces) by either themselves or else in combination with each other and/or characterized by their relatively high solubility in [the] suitable liquid medium. Paragraph [0002]. US 2004/0105881 specifically discloses that "incorporation of a surfactant into a bilayer membrane that is built from another less soluble amphiphat, such as a phospholipid, can increase the flexibility of the resulting complex membrane . promoting] the capability of complex aggregates . to cross pores in a semi-permeable membrane that otherwise would prevent comparably large aggregates from crossing." Paragraph [0015]. Citation of any reference in this section of the application is not an admission that the reference is prior art to the application. The above noted publications are hereby incorporated by reference in their entirety. 3. SUMMARY OF THE INVENTION [0006] Provided herein are compositions and methods related to vesicular formulations that include one or more phospholipids and one or more nonionic surfactants. In some embodiments, the formulations are effective for the delivery of fatty acids and/or phospholipids in the treatment of disorders related to fatty acid metabolic disorders, including essential fatty acid deficiency. In a particular embodiment, the vesicular formulations include about 25% to about 30% surfactant by weight based on the total weight of the vesicular formulation. These vesicular formulations are suitable for any method of administration, e.g., subcutaneously, topically, or intravenously. [0007] The term "formulation" as used herein refers to any composition as described herein, for example, a formulation that includes one or more phospholipids and one or more nonionic surfactants. In some embodiments a formulation may include one or more active agents as described herein; in other embodiments a formulation may specifically not include any active agents, for example active agents as disclosed herein. In some embodiments (for example embodiments that may be useful for agricultural purposes), the formulation may include an active agent that is selected from the group consisting of an acaricide, avicide, herbicide, insecticide, molluscicide, virucide, algicide, antibiotic, bactericide, fungicide, nematicide, pesticide, rodenticide, plant growth regulator, seed treatment, chemosterilant, insect attractant, mammal repellent, antifeedant, bird repellant, herbicide safener, insect repellant, mating disrupter, plant activator, synergist, and/or the like. In certain embodiments, the formulation includes one or more active agents selected from the agents listed on Table 9. In some embodiments, the formulation does not include any of the active agents listed on Table 9. In some embodiments, a formulation includes ingredients or components as described herein, for example such as described in Table 8A and Table 8B. In various embodiments, a formulation similar to or the same as the Example Formulations 1- 129; in some embodiments, the formulations are similar or the same as the Example Formulations 1-129 except they further include at least one active agent such as described herein (for example the active agent may be present in the formulation in an amount as described herein). In certain embodiments, a formulation, such as described herein (especially those for use in agricultural applications and methods), is not suitable for administration to a human, for example, it does not meet criteria required by a government regulatory agency such as the United States Food and Drug Administration (FDA). In some embodiments, the formulation is suitable for use in agriculture, for example it is suitable to apply to plants and crops intended for human consumption. In certain embodiments, the formulation is suitable for administration to a human as a pharmaceutical compositon, for example it
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