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WO 2012/167920 Al 13 December 2012 (13.12.2012) P O P C T

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WO 2012/167920 Al 13 December 2012 (13.12.2012) P O P C T (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 WO 2012/167920 Al 13 December 2012 (13.12.2012) P O P C T (51) International Patent Classification: (74) Agents: BORJES-PESTALOZZA, Henrich et al; PAT A01N 43/14 (2006.01) C07H 15/04 (2006.01) ENT- UND RECHTSANWALTE, MAUCHER BORJES A01N 63/02 (2006.01) C12P 19/44 (2006.01) JENKINS, Urachstrasse 23, 79102 Freiburg i. Br. (DE). (21) International Application Number: (81) Designated States (unless otherwise indicated, for every PCT/EP2012/002399 kind of national protection available): AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, (22) Date: International Filing CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, DO, 6 June 2012 (06.06.2012) DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, (25) Filing Language: English HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, (26) Publication Language: English MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, (30) Priority Data: OM, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SC, SD, 11004776.8 10 June 201 1 (10.06.201 1) EP SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (71) Applicant (for all designated States except US): IN- TERMED DISCOVERY GMBH [DE/DE]; Ot- (84) Designated States (unless otherwise indicated, for every to-Hahn-Strasse 15, 44227 Dortmund (DE). kind of regional protection available): ARIPO (BW, GH, GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, SZ, TZ, (72) Inventors; and UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, TJ, (75) Inventors/Applicants (for US only): STADLER, Marc TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, [DE/DE]; Hauptstrasse 120, 67150 Niederkirchen (DE). EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, ΓΓ, LT, LU, LV, BITZER, Jens [DE/DE]; Wildrosenstrasse 30, 44225 MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, Dortmund (DE). KOPCKE, Barbel [DE/DE]; Baroper TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, Schulstrasse 1A, 44225 Dortmund (DE). REINHARDT, ML, MR, NE, SN, TD, TG). Kathrin [DE/DE]; Am Beisenufer 12, D-44225 Dortmund (DE). MOLDENHAUER, Jana [DE/DE]; Feldbank 72, Published: 44265 Dortmund (DE). — with international search report (Art. 21(3)) [Continued on next page] (54) Title: LONG CHAIN GLYCOLIPIDS USEFUL TO AVOID PERISHING OR MICROBIAL CONTAMINATION OF MA TERIALS (57) Abstract: The invention relates to the use of, OH and methods of use employing, certain glycolipid compounds as defined in detail below and having Η — H3c r i sr - - , preservative or antimicrobial properties, novel com OH pounds of the glycolipid class, and related invention OH embodiments. The compounds have the formula (I) wherein m is (3) to (5), n is (2) to (5), o is (0) or (1) and p is (3) to (17), with the proviso that the sum m + n + o + p is not less than (14); and R is a carbo hydrate moiety bound via one of its carbon atoms to the binding oxygen, and/or a physiologically, espe cially pharmaceutically or nutraceutically or cosmet ically, acceptable salt thereof, or an ester thereof, as such or in the form of a composition, where the com pound may be present in open chain form and/or in the form of a lactone. o Fig. 1 o w o 2012/167920 Al III III II II III III I I III llll l I II III II I II before the expiration of the time limit for amending the — with (an) indication^) in relation to deposited biological claims and to be republished in the event of receipt of material furnished under Rule 13bis separately from the amendments (Rule 48.2(h)) description (Rules 13bis.4(d)(i) and 48.2(a)(viii)) with sequence listing part of description (Rule 5.2(a)) Long chain glycolipids useful to avoid perishing or microbial contamination of materials Summary of the invention The invention relates to the use of, and methods of use employing, certain glycolipid compounds as defined in detail below and having preservative or antimicrobial properties, novel compounds of the glycolipid class, and related invention embodiments. These and related invention embodiments are described below and in the claims which are incorporated into the specification by reference. Background of the invention Bacteria and other microbial organisms cause food and beverage products, cosmetic and home care products as well as other products to go bad, thereby reducing the shelf life or useful life of such products or goods. Thus, numerous efforts have been made to reduce the deleterious effects of microbial contaminants in food and beverage products, cosmetics, dressing material and other materials, e.g. medical devices such as implants. Other food preservatives such as salt, sugar and vinegar have been used for generations and while relatively safe to use, their preservative effect is limited in both duration of effect and the types of food and beverages for which they can be used. In addition, at higher levels, preservatives such as salt and vinegar can affect the taste of the product. Commonly used preservatives for cosmetics include antimicrobial agents such as quaternary ammonium compounds, alcohols, chlorinated phenols, parabens and paraben salts, imidazolidinyl urea, phenoxyethanol, p-hydroxybenzoate, small carboxylic acids like benzoic acid, sorbic acid, salicylic acid, formic acid, proponic acid or corresponding salts. Formaldehyde-releasers and isothiazolinones may also be used. However, these materials often may not be tolerated or, e.g. in the case of formaldehyde, may even be toxic and even carcinogenic, or they may cause allergies or food intolerance. Another preservative e.g. used in food and especially beverages is sulfuric acid, while in meat products, e.g. sausages, preserved meat and meat, stabilizers which decrease water activity such as potassium and/or sodium nitrites and nitrates are often added. Also smoke is often used for preserving meat products, with the undesirable side effect of formation of polycyclic aromatic hydrocarbons which have carcinogenic properties. Food and beverages have varying degrees of sensitivity to microbiological spoilage depending on intrinsic factors of the food or beverage such as pH, nutrient content (e.g., juice, vitamin, or micronutrient content), carbonation level, Brix (an indicator of sugar content), water quality (e.g., alkalinity and/or hardness), and preservatives. Spoilage events occur when microorganisms are able to overcome the product's intrinsic protection factors and grow. The microorganisms' ability to overcome these hurdles can be influenced by, among other things, initial contamination level, temperature, water content, e.g. water activity, and package integrity. Of special importance are also recurrent contaminations of cosmetics, e.g. by hand contact during normal use. A number of organisms are responsible for spoiling a variety of beverages materials, including cold-filled beverages. Yeasts such as Saccharomyces, Zygosaccharomyces, Candida, and Dekkera spp. are most common. Also, acidophilic bacteria such as Lactobacillus, Leuconostoc, Gluconobacter, and Zymomonas spp., and molds like Penicillium, Aspergillus and Mucor spp. can spoil various water containing materials. Other materials and also other types of beverages are susceptible to spoilage by microorganisms. Spores of acidophilic, thermophilic bacteria, such as Alicyclobacillus spp., and heat resistant mold spores of Byssochlamys, its anamorphic (asexual) stages Paecilomyces, and Neosartorya spp. can survive pasteurization and may spoil non- carbonated, hot-filled products such as sport drinks and teas. Also, packaged waters are susceptible to contamination by molds. In cosmetic, personal care and home care products spoilage occurs by a variety of micro organisms, ranging from Gram-positive bacteria (e.g. Staphylococcus spp.), Gram-negative bacteria (e.g. Escherichia coli, Pseudomonas spp.) to yeasts (e.g. Candida albicans) and common molds (e.g. Aspergillus niger). Microbial growth in or on these products depends on several instrinsic factors such as water activity of the formulation (minimum water activity requirements for growth or proliferation range from 0.99 for Acinetobacter species down to 0.61 for some fungal species), formulation composition, pH value (e.g., optimum pH for the growth of most yeasts and molds is between 4.0 and 6.0), and processing conditions such as temperature. While high temperatures, e.g. 80 °C for 20 minutes, may reduce microbial contaminations during processing, it is important to prevent inactivation or degradation of the preservatives in the formulation. Furthermore, product packaging, solubility of the preservative and its antimicrobial susceptibility profile will influence preserving efficacy and, consequently, the shelf life of the products. Protection against microbiological spoilage of sensitive products can be achieved using chemical preservatives and/or processing techniques such as hot filling, tunnel pasteuriza¬ tion, ultra-high temperature (UHT), or pasteurization followed by aseptic packaging, and/or pasteurization followed by chilling the beverage. Generally, beverages with a pH < 4.6 can be chemically preserved, heat processed, and filled into packages such that the product is not re-contaminated. For example, process techniques such as cold-filling, followed by chemical preservatives or pasteurization with cold filling, may be used to preserve a cold- filled beverage. In a similar manner, this same beverage may be processed using non- preserved techniques such as hot filling, tunnel pasteurization, pasteurization followed by aseptic filling, or requiring the beverage to be chilled, i.e., under refrigeration following the pasteurization step. Beverages having a pH 2 - 4.6 must be processed such that spores are destroyed using ultra-high temperatures followed by aseptic filling into packages or by using a retort.
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