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Wo 2009/120182 A2 (12) INTERNATIONALAPPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date 1 October 2009 (01.10.2009) WO 2009/120182 A2 (51) International Patent Classification: AO, AT, AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, A61K 47/34 (2006.01) CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, (21) International Application Number: HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, PCT/US2008/013816 KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, (22) International Filing Date: MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, 18 December 2008 (18.12.2008) NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TJ, TM, TN, TR, TT, TZ, UA, (25) Filing Language: English UG, UZ, VC, VN, ZA, ZM, ZW. (26) Publication Language: English (84) Designated States (unless otherwise indicated, for every (30) Priority Data: kind of regional protection available): ARIPO (BW, GH, 61/015,365 20 December 2007 (20.12.2007) US GM, KE, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, 12/262,986 31 October 2008 (3 1.10.2008) US ZW), Eurasian (AM, AZ, BY, KG, KZ, MD, RU, TJ, TM), European (AT, BE, BG, CH, CY, CZ, DE, DK, EE, (71) Applicant: EASTMAN CHEMICAL COMPANY [US/ ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, US]; 200 South Wilcox Drive, Kingsport, TN 37660 MC, MT, NL, NO, PL, PT, RO, SE, SI, SK, TR), OAPI (US). (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG). (72) Inventor: WEMPE, Michael, Fitzpatrick; 4016 Rick Slaughter Court, Kingsport, TN 37660 (US). Published: (74) Agent: NELSON, Brett, L.; P.O. Box 5 11, Kingsport, — without international search report and to be republished TN 37662-5075 (US). upon receipt of that report (Rule 48.2(g)) (81) Designated States (unless otherwise indicated, for every kind of national protection available): AE, AG, AL, AM, (54) Title: SULFO-POLYMER POWDER AND SULFO-POLYMER POWDER BLENDS WITH CARRIERS AND/OR AC TIVES Figure 1 AQ38S (Left) and AQ38P (Right) Comparison (57) Abstract: Sulfo-polyester powders and sulfo-polyester blend powders, the incorporation of carriers and/or actives, and meth ods of making the powders as well as dispersions employing these powders. SULFO-POLYMER POWDER AND SULFO-POLYMER POWDER BLENDS WITH CARRIERS AND/OR ACTIVES BACKGROUND OF THE INVENTION: Sulfo-polyesters (such as Eastman AQ polymers) are high molecular weight amorphous polyesters commonly dispersed directly in water without the need to incorporate organic co-solvents, surfactants, or amines. Sulfo-polyesters differ chiefly by their chemical makeup (i.e. they are composed of 5-sodiosulfoisophthalic acid (5- SSIPA) and various combinations of other materials, for example: terephthalic acid (TPA), isophthalic acid (IPA), ethylene glycol (EG), diethylene glycol (DEG), 1,4- cyclohexanedimethanol (CHDM), and/or 1,4-cyclohexanedicarboxylic acid (1,4- CHDA). The temperature where a glassy polymer becomes rubbery on heating, and vice versa upon cooling, is known as the 'glass transition temperature (Tg). Hence, the various sulfo-polyester polymers have different average Tg values. Sulfopolyesters are solid to semi-solid polymers and require warm to hot water with sufficient mixing time to prepare concentrated dispersions. Moreover, different sulfo-polyester polymer dispersions may possess trace volatile components and potentially cause odor. Therefore methods that improve dissolution and/or lower volatile content may be advantageous. BRIEF SUMMARY OF THE INVENTION: The present invention addresses solutions to issues previously described and enables the preparation of sulfopolyester polymer powders and/or blends containing carriers (e.g. surfactants) and/or actives, and dispersions of sulfopolyester or sulfopolyester blends with and without carriers and/or actives, having reduced odor, using water and/or solvent mixtures with sufficient mixing. An embodiment of the present invention concerns a composition comprising at least one sulfonated copolyester and at least one active agent, wherein said composition is a powder. Yet another embodiment concerns a method of increasing the bioavailability of an active agent comprising administering the composition described in the previous paragraph to a subject (i.e. an organism). Another embodiment concerns a method for producing a sulfonated copolyester powder containing an active agent comprising: a) dispersing at least one sulfonated coployester and at least one active agent in a solvent, or solvent mixture, to form a dispersion; and b) drying said dispersion to form a powder. Another embodiment concerns a method for producing a sulfonated copolyester powder containing an active agent comprising: a) dispersing at least one sulfonated copolyester in a solvent to form a dispersion; and b) drying said dispersion to form a powder; and c) mixing (grinding, milling, and the like) said sulfonated copolyester powder with at least one active agent. Yet another embodiment concerns a cosmetic composition, comprising the compositions described above and a cosmetically acceptable carrier. Another embodiment concerns a pharmaceutical or agricultural composition, comprising the compositions described above and a pharmaceutically or agriculturally acceptable carrier. BRIEF DESCRIPTION OF THE DRAWINGS Figure 1 shows a side-by-side comparison of a sulfopolyester polymer and the corresponding powder. Figure 2 shows the chemical structures for various compound examples incorporated with sulfopolyester polymer powders. Figure 3A shows the oral dose blood concentration-time data for itraconazole for two dosing groups; and Figure 3B shows the oral dose blood concentration-time data for hydroxy- itraconazole for two dosing groups. DETAILED DESCRIPTION: The present invention concerns sulfo-polyester powders and sulfo-polyester blend powders, the incorporation of carriers and/or actives, and methods of making the powders as well as dispersions employing these powders. Sulfo-polyester powder(s) and sulfo-polyester powder blend(s) with and without carriers and/or actives are prepared by dispersing said sulfo-polyester powder(s) and sulfo-polyester powder blend(s) in a solvent or solvent mixture (e.g.. water, water and alcohol mixtures, etc) at various temperatures. The exact solvent, or solvent mixture, and temperatures used will be a function of the application end usage and/or required dispersion percentage. End uses of said sulfo-polyester powder(s) and sulfo-polyester powder blend(s) include sun care /skin care applications (i.e. creams, lotions and sprays), perfume applications (i.e. flavors, fragrances, essential oils, etc), hairstyling applications (i.e. hair gel and hairspray), color makeup and hairstyling applications, drug-delivery applications, and adhesive removal such as re-pulping of paper and plastic and glass recycling. As used throughout this application, the term "powder" shall mean particles in the range of 0.5 - 5000 µM. The science and technology of small particles is known as "micrometrics" (for a general review, see 'Physical Pharmacy and Pharmaceutical Sciences' Fifth Edition by Patrick J. Sinko, Lippincott Willams & Wilkins, 2006, ISBN: 0-7817-5027-X). The unit commonly used to describe particle size is the micrometer (µm). In general, optical microscopy may be used to measure particle- sizes of about 0.2 to about 100 µm; however, other techniques may also be used to determine approximate size ranges, such as sedimentation, coulter counter, airpermeability, sieving, etc. Techniques such as sieving, according to methods of the U.S. Pharmacopeia, may be used to determine 'powder fineness1, or other properties of the corresponding powders and/or powder blends; for example, particle size and size distribution (i.e. average particle size, particle-size distribution (frequency distribution curve), number and weight distributions, particle number), particle volume, particle shape and surface area, pore size, porosity, particle density, bulkiness, flow properties, etc. Because many powders have a tendency to contain a non-symmetric particle size distribution, it is common to plot the log-normal distribution; commonly, this method results in a linear relationship. Subsequently, the "geometric mean diameter" (dg; the particle size equivalent to 50% on the probability scale) may be obtained from plotting the logarithm of the particle size against the cumulative percent frequency on a probability scale. Therefore, as used throughout this application, powders shall be classified into different particle size ranges, such as: 'extremely fine powders' (i.e. dusty powders; 0.5-50 µm), 'fine powders' (50-100 µm), 'coarse powders' (100-1000 µm), and 'granular powders' (1000-5000 µm). In an embodiment of the present invention, the compositions are generally prepared by techniques such as lyophilization, spray-drying, jet milling, spray freeze- drying, fluidized-bed spray coating, supercritical fluid methods, etc. The different techniques are based on different mechanisms of droplet/particle formation and/or drying (for a general review, see 'Lyophilization of Biopharmaceuticals' edited by Henry R. Costantino and Michael J. Pikal, AAPS Press, 2004, ISBN: 0-971 1767-6-0). The compositions are prepared by dispersing a sulfo-polyester or sulfo- polyester blend in a solvent, or solvent mixture (e.g. water, water and alcohol mixtures, etc), and optionally at least one active at various temperatures to form a dispersion. The dispersion can also include a carrier. The starting sulfo-polyester or sulfo-polyester blend can be in pellet form, or, for example, can be a sample that has been chipped or ground up. The exact solvent, or solvent mixture, and temperatures used will be a function of the application end usage and/or required dispersion percentage. Typical starting dispersions contain about 35% to about 2% by weight sulfo- polyester or sulfo-polyester blend, or between about 25% to about 5% weight sulfo- polyester or sulfo-polyester blend, or between about 15% to about 7% by weight sulfo-polyester or sulfo-polyester blend.
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