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(12) United States Patent (10) Patent No.: US 8,187,615 B2 Friedman (45) Date of Patent: May 29, 2012

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US008187615B2 (12) United States Patent (10) Patent No.: US 8,187,615 B2 Friedman (45) Date of Patent: May 29, 2012 (54) NON-AQUEOUS COMPOSITIONS FOR ORAL 6,054,136 A 4/2000 Farah et al. DELIVERY OF INSOLUBLE BOACTIVE 6,140,375 A 10/2000 Nagahama et al. AGENTS 2003/O149061 A1* 8/2003 Nishihara et al. .......... 514,266.3 FOREIGN PATENT DOCUMENTS (76) Inventor: Doron Friedman, Karme-Yosef (IL) GB 2222770 A 3, 1990 JP 2002-121929 5, 1990 (*) Notice: Subject to any disclaimer, the term of this WO 96,13273 * 5/1996 patent is extended or adjusted under 35 WO 200056346 A1 9, 2000 U.S.C. 154(b) by 1443 days. OTHER PUBLICATIONS (21) Appl. No.: 10/585,298 Pouton, “Formulation of Self-Emulsifying Drug Delivery Systems' Advanced Drug Delivery Reviews, 25:47-58 (1997). (22) PCT Filed: Dec. 19, 2004 Lawrence and Rees, “Microemulsion-based media as novel drug delivery systems' Advanced Drug Delivery Reviews, 45:89-121 (86). PCT No.: PCT/L2004/OO1144. (2000). He et al., “Microemulsions as drug delivery systems to improve the S371 (c)(1), solubility and the bioavailability of poorly water-soluble drugs' (2), (4) Date: Jul. 6, 2006 Expert Opin. Drug Deliv. 7:445-460 (2010). Prajpati et al. “Effect of differences in Fatty Acid Chain Lengths of (87) PCT Pub. No.: WO2005/065652 Medium-Chain Lipids on Lipid/Surfactant/Water Phase Diagrams PCT Pub. Date: Jul. 21, 2005 and Drug Solubility” J. Excipients and Food Chem, 2:73-88 (2011). (65) Prior Publication Data * cited by examiner US 2007/O190O80 A1 Aug. 16, 2007 Primary Examiner — Robert A Wax Assistant Examiner — Jessica Worsham (30) Foreign Application Priority Data (74) Attorney, Agent, or Firm — Browdy and Neimark, Jan. 6, 2004 (ID) ......................................... 159729 PLLC (51) Int. Cl. (57) ABSTRACT A6 IK9/00 (2006.01) The present invention provides a composition of low water A6 IK38/00 (2006.01) solubility drug, dissolved or dispersed in a non crystalline or A6 IK 4.8/00 (2006.01) low crystalline form in an emulsion type composition of A6 IK3I/70 (2006.01) internal oily-solvent and external non-hydrous and water (52) U.S. Cl. ........... 424/400: 514/1.1 : 514/44 R: 514/23 soluble solvent, whereas 1) emulsifying stabilizer comprises (58) Field of Classification Search ........................ None low fraction of the composition, and 2) emulsions of mean See application file for complete search history. droplets size below one micron is obtained upon dilution with physiological fluids, and 3) facilitated dispersion of biologi (56) References Cited cally active agents in body fluids is obtained, and more par ticularly to facilitating biological availability or improving U.S. PATENT DOCUMENTS clinical performance. 5,342,625 A * 8, 1994 Hauer et al. .................. 424/455 5,965,160 A 10, 1999 Benita et al. 5,993,858 A 11/1999 Crison et al. 20 Claims, No Drawings US 8,187,615 B2 1. 2 NON-AQUEOUS COMPOSITIONS FOR ORAL ultimately the triglyceride must be digested and the therapeu DELIVERY OF INSOLUBLE BOACTIVE tic agent must be released in order to be absorbed through the AGENTS intestinal mucosa. Certain Surfactants commonly used in the preparation of The present invention provides a composition of low water 5 pharmaceutical emulsions, such as polyethoxylated castor solubility drug, dissolved or dispersed in a non crystalline or oils, may themselves act as inhibitors of lipolysis. Although low crystalline form in an emulsion type composition of recent work Suggests that certain Surfactant combinations, internal oily-solvent and external non-hydrous and water when used in combination with digestible oils in emulsion soluble solvent, whereas 1) emulsifying stabilizer comprises preparations, can Substantially decrease the lipolysis-inhibit low fraction of the composition, and 2) emulsions of mean 10 ing effect of some common pharmaceutical Surfactants (U.S. droplets size below one micron is obtained upon dilution with Pat. No. 5,645,856), such formulations are still subject to the physiological fluids, and 3) facilitated dispersion of biologi other disadvantages of pharmaceutical emulsions and triglyc cally active agents in body fluids is obtained, and more par eride-based formulations. ticularly to facilitating biological availability or improving Example of self emulsifying system is described in U.S. clinical performance. 15 Pat. No. 6,054,136 (Faraha et al). The invention relates to a composition which can be administered, in particular, orally, BACKGROUND OF INVENTION for pharmaceutical or cosmetic use, capable of forming a micro-emulsion in situ with the biological fluid of the body; The formulation of lipophilic, amphipathic, or sparingly the invention relates more especially to a composition pro water-soluble drugs for oral administration has proven to be viding of a self-micro-emulsifying carrier system for active difficult, since in order to be absorbed, drugs need to be agents, designated in the art by the English term “SMEDDS solubilized in the gastro intestinal fluids which are hydrous (self-micro-emulsifying drug delivery system); these systems and therefore are intrinsically not favorable medium for such have the property of emulsifying in water at the temperature insoluble bioactive molecules. of the human body. Oral drug delivery vehicles must be capable of maintaining 25 This composition as well as otherself emulsifying compo sufficient drug concentration in a bio-available form that will sitions are intended, on the one hand to transport one or more enable expected absorption and biological activity. Such drug soluble or sparingly soluble active agents, and on the other delivery vehicles must also be capable of maintaining the hand to form a micro-emulsion with the biological fluid of the drug in its dissolved state and maintain stability of drug and human body, being understood that one or more active agents dosage form over an extended storage period while avoiding 30 or principles in Solution in a micro-emulsion has better bio the use of physiologically harmful solvents or excipients. availability. However, the self emulsifying systems possess Dissolved state, which enables transport of drug from the major drawback, of typical high surfactant content in the gastro intestinal fluids into the blood circulation, is a state range of 20 to 50%. where single drug molecules are exists individually in the High Surfactant concentration may inhibit lipolysis and is fluid medium. 35 disadvantageous to the intestinal mucous and has potential of One approach to overcome drugs molecules self attraction causing local irritation side effects. and maintain hydrophobic drugs in dissolved or solubilized Thus, there is a need for pharmaceutical compositions that state at the gastro intestinal absorptive mucous is by high overcome the limitations of conventional micelle formula Surfactants content delivery systems. Such as, micelles, self tions, but without Suffering from the disadvantages of trig emulsifying micro-emulsions and related colloidal systems. 40 lyceride-containing formulations or disadvantage of high Sur Micelles are agglomerates of colloidal dimensions formed factant ratio. by amphiphilic compounds or Surfactants. In aqueous solu A need therefore exists in the art of drug delivery to develop tion, micelles can incorporate hydrophobic therapeutic a vehicle that can be used with lipophilic and amphipathic agents in the hydrocarbon core of the micelle. Loading capac insoluble materials, drugs or nutrients and that can be stored ity of micelle formulations is limited by the solubility of the 45 at various temperatures for extended periods of time and be therapeutic agent in the micelle Surfactant and dosage form is dilutable or spontaneously mixing with an aqueous fluid Such intrinsically of high Surfactant ratio. as blood or a buffer solution or gastro-intestinal fluids and Another conventional approach is dissolving hydrophobic deliver the drug to the absorption organ or membrane in a drugs in oily medium Such as triglyceride-based solvents. functional form. This oily solution of lipophilic drug in oily phase may be 50 In particularly, there is a need for such vehicle that will not further processed in two ways. One way is emulsifying in comprise high and significant portion of Surfactants that are aqueous medium by the aid of Surfactants, to produce an irritating to the gastro intestinal mucous. oil-in-water emulsion, which are inherently unstable dosage It is the objective of the present invention to furnish a form, and second way is adding high amount of Surfactant to carrier system for bioactive agents having limited water solu produce thermodynamically stable micro-emulsions prefer 55 bility, whereas an admixture to body fluid is possible or better able self-emulsifying upon dilution in the gastrointestinal dissolution and enhanced absorption is obtained while avoid fluids. The properties of these oil-based formulations are ing the side effects associated with high emulsifiers concen determined by such factors as the size of the triglyceride/ tration. therapeutic agent colloidal particles and the presence or Unexpectedly, it has now been discovered that one: it is absence of Surfactant additives. Size control is a significant 60 possible to formulate significant amount of hydrophobic factor affecting absorption, Smaller particles resulting in bet waterinsoluble drugs in the low surfactant, oil in non-hydrous ter absorption. Solvent, stable emulsion system composition, in a dissolved A further disadvantage of triglyceride-containing compo amorphous state. Two: good mixing of nano size droplets in sitions is the dependence of therapeutic agent absorption on the gastro intestinal fluids is obtained despite low surfactant the rate and extent of lipolysis. Although colloidal emulsion 65 concentration, and three: facilitate drug dissolution formu particles can transport hydrophobic therapeutic agents lated with this system and four: maintaining stable amor through the aqueous environment of the gastrointestinal tract, phous or low crystalline state of drugs in the composition. US 8,187,615 B2 3 4 PRIOR ART non-hydrous emulsion with mean droplet size below one micron, comprising at least one low solubility bioactive com U.S.
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    Brazilian Journal of Chemical ISSN 0104-6632 Printed in Brazil Engineering www.scielo.br/bjce Vol. 34, No. 03, pp. 659 – 669, July – September, 2017 dx.doi.org/10.1590/0104-6632.20170343s20150669 FATTY ACIDS PROFILE OF CHIA OIL-LOADED LIPID MICROPARTICLES M. F. Souza1, C. R. L.Francisco1; J. L. Sanchez2, A. Guimarães-Inácio2, P. Valderrama2, E. Bona2, A. A. C. Tanamati1, F. V. Leimann2 and O. H. Gonçalves2* 1Universidade Tecnológica Federal do Paraná, Departamento de Alimentos, Via Rosalina Maria dos Santos, 1233, Caixa Postal 271, 87301-899 Campo Mourão, PR, Brasil. Phone/Fax: +55 (44) 3518-1400 2Universidade Tecnológica Federal do Paraná, Programa de Pós-Graduação em Tecnologia de Alimentos, Via Rosalina Maria dos Santos, 1233, Caixa Postal 271, 87301-899 Campo Mourão, PR, Brasil. Phone/Fax: +55 (44) 3518-1400 *E-mail: [email protected] (Submitted: October 14, 2015; Revised: August 25, 2016; Accepted: September 6, 2016) ABSTRACT - Encapsulation of polyunsaturated fatty acid (PUFA)is an alternative to increase its stability during processing and storage. Chia (Salvia hispanica L.) oil is a reliable source of both omega-3 and omega-6 and its encapsulation must be better evaluated as an effort to increase the number of foodstuffs containing PUFAs to consumers. In this work chia oil was extracted and encapsulated in stearic acid microparticles by the hot homogenization technique. UV-Vis spectroscopy coupled with Multivariate Curve Resolution with Alternating Least-Squares methodology demonstrated that no oil degradation or tocopherol loss occurred during heating. After lyophilization, the fatty acids profile of the oil-loaded microparticles was determined by gas chromatography and compared to in natura oil.