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WO 2017/207569 Al 07 December 2017 (07.12.2017) W !P O PCT

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WO 2017/207569 Al 07 December 2017 (07.12.2017) W !P O PCT (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 2017/207569 Al 07 December 2017 (07.12.2017) W !P O PCT (51) International Patent Classification: Declarations under Rule 4.17: C13B 30/02 (20 11.0 1) A23L 33/10 (20 16.0 1) — as to applicant's entitlement to apply for and be granted a C13B 50/00 (201 1.01) A61K 47/26 (2006.01) patent (Rule 4.1 7(H)) A23L 27/30 (2016.01) A61K 33/14 (2006.01) — as to the applicant's entitlement to claim the priority of the (21) International Application Number: earlier application (Rule 4.17(Hi)) PCT/EP2017/063038 — of inventorship (Rule 4.1 7(iv)) (22) International Filing Date: Published: 30 May 2017 (30.05.2017) — with international search report (Art. 21(3)) (25) Filing Language: English (26) Publication Langi English (30) Priority Data: 16172630.2 02 June 2016 (02.06.2016) EP (71) Applicant: NESTEC S.A. [CH/CH]; Avenue Nestle 55, 1800 VEVEY (CH). (72) Inventors: OERTLING, Heiko; 41, Avenue du Temple, 1012 Lausanne (CH). ALZIEU, Thibaut; 44, Chemin de la Beree, 1010, 1010 Lausanne (CH). VINAY, Claire; 855, chemin de Soubredioux, Quartier Caillat, 26320 Saint Mar- cel-Les-Valence (FR). BORLET, Celine; 83, Chemin de la Petite Foret, 73260 Aigueblanche (FR). (74) Agent: COUZENS, Patrick; Nestle Research Center, Vers-chez-les-Blanc, 1000 Lausanne 26 (CH). (81) Designated States (unless otherwise indicated, for every kind of national protection available): AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DJ, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IR, IS, JP, KE, KG, KH, KN, KP, KR, KW, KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY,TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (84) Designated States (unless otherwise indicated, for every kind of regional protection available): ARIPO (BW, GH, GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, 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, GW, KM, ML, MR, NE, SN, TD, TG). o l (54) Title: CO-CRYSTALLINE SUCROSE © (57) Abstract: The invention relates to nutritional or pharmaceutical compositions comprising sucrose* calcium salt co-crystals and to the use of sucrose'calcium salt co-crystals for calcium fortification of nutritional compositions. The invention further relates to a process for preparing sucrose* calcium salt co-crystals. Co-crystalline sucrose Field of the Invention The invention relates to nutritional or pharmaceutical compositions comprising sucrose · calcium salt co-crystals and to the use of sucrose · calcium salt co-crystals for calcium fortification of nutritional compositions. The invention further relates t o a process for preparing sucrose · calcium salt co-crystals. Background of the Invention Calcium, the most abundant mineral in the human body, is essential for bone health and teeth development and plays a role in the prevention of developing osteoporosis. Furthermore, calcium is essential in cell physiology, in particular in its role as second messenger, i.e. an intracellular signaling mineral involved in various cellular processes such as proliferation, differentiation, migration and apoptosis. Flux of calcium ions into and out of the cytoplasm functions as a signal for various cellular processes. Since the body does not produce minerals, it is dependent on an external supply of calcium. An external supply of calcium may for example be provided by fortified nutritional products. Fortification is an increase of the content of essential micronutrients, i.e. vitamins and minerals (e.g. calcium). In this respect, however, selection of an appropriate form of calcium, which supplements the desired level of the mineral without affecting flavour, solubility, bioavailability, processability and organoleptic properties of the product is challenging. Addition of calcium to milk, for example, is associated with significant difficulties. Direct addition of calcium salts to milk is likely to result in precipitation of calcium complexes of milk proteins. Many potential calcium fortificants are limited in the levels at which they can be applied due to perceived grittiness and bitterness, e.g. calcium sulphate and calcium phosphates. In addition, various calcium salts commonly used for fortification purposes (e.g. calcium citrate malate, tricalcium phosphate or calcium lactate) are characterized by poor flowability rendering their handling and dosage impractical. Many calcium salts absorb moisture from their environment, leading t o caking which can block dosing systems and result in loss of entire production batches. Accordingly, a need exists for solid dosing forms for the mineral calcium, which have good solubility, are flowable and do not absorb moisture and lead to caking, for example in powder formulations. Thus, it is an object of the present invention to provide an efficient way of calcium fortification in nutritional or pharmaceutical compositions. Any reference to prior art documents in this specification is not to be considered an admission that such prior art is widely known or forms part of the common general knowledge in the field. As used in this specification, the words "comprises", "comprising", and similar words, are not to be interpreted in an exclusive or exhaustive sense. In other words, they are intended to mean "including, but not limited to". Summary of the invention An object of the present invention is t o improve the state of the art and to provide compositions overcoming at least some of the inconveniences described above or at least providing a useful alternative. The object of the present invention is achieved by the subject matter of the independent claims. The dependent claims further develop the idea of the present invention. Accordingly, the present invention provides in a first aspect a nutritional or pharmaceutical composition comprising sucrose · calcium salt co-crystals. A second aspect of the invention relates to the use of sucrose · calcium salt co-crystals for calcium fortification of nutritional compositions. In a third aspect, the invention relates to a process for preparing sucrose · calcium salt co-crystals comprising the steps of preparing a solution comprising a calcium salt and sucrose at a temperature of 70- 90 °C, cooling the solution t o 20-35 °C, adding seeding crystals of sucrose · calcium salt co-crystals, allowing the formation of crystals, and isolating the obtained crystals. It was unexpectedly found that calcium fortification of the nutritional or pharmaceutical compositions is achieved by employing calcium salts in their co- crystalline form with sucrose, offering a novel crystalline, flowable and stable dosing form for supplementary mineralization. Fructose · calcium halide co-crystals have been reported t o be very hygroscopic [Heidar-Ali Tajmir-Riahi, Journal of Inorganic Biochemistry 27, 123-131 (1986)], so the inventors were surprised t o find that sucrose · calcium salt co-crystals could be used in formulations, for example powder formulations, without problems of moisture absorption. Sucrose · calcium salt co-crystals have previously been described in the literature [F.T.Jones et al., Microscopy & Crystal Front 13(12), 346-50, (1963)], but their hygroscopic properties have not been examined, nor has their use in nutritional or pharmaceutical compositions been proposed. Brief Description of the Drawings Figure 1 shows a single crystal structure elucidation via X-ray diffraction of Sucrose · CaCI 2 4 H20 . Figure 2 shows powder X-ray diffraction patterns of a) top: pure CaCI 2 · 2 H20 , b) middle: pure Sucrose and c) bottom: Sucrose · CaCI 2 · 4 H20 . The x-axis is 2-theta (in degrees) and the y-axis is intensity (counts). Figure 3 shows a single crystal structure elucidation via X-ray diffraction of Sucrose · CaBr2 · 4 H20 . Figure 4 shows powder X-ray diffraction patterns of a) top: pure CaBr2 · 2 H20 , b) middle: pure Sucrose and c) bottom: Sucrose · CaBr2 · 4 H20 by slurry ripening in acetone. The x-axis is 2-theta (in degrees) and the y-axis is intensity (counts). Figure 5 shows water uptake in maltodextrin powder with the addition of different ♦ calcium containing materials: powder matrix alone ( ) powder matrix with CaCI 2 · 2 H20 (·), powder matrix with co-crystalline Sucrose · CaCI 2 · 4 H20 (A), and powder matrix with the equivalent dry-mix CaCI 2 · 2 H20 + sucrose (■ ). Figure 6 shows water uptake in skimmed milk powder with the addition of different ♦ calcium containing materials: powder matrix alone ( ) powder matrix with CaCI 2 · 2 H20 (·), powder matrix with co-crystalline Sucrose · CaCI 2 · 4 H20 (A), and powder matrix with the equivalent dry-mix CaCI 2 · 2 H20 + sucrose (■ ). Figure 7 shows water uptake in full cream milk powder with the addition of different ♦ calcium containing materials: powder matrix alone ( ) powder matrix with CaCI 2 · 2 H20 (·), powder matrix with co-crystalline Sucrose · CaCI 2 · 4 H20 (A), and powder matrix with the equivalent dry-mix CaCI 2 · 2 H20 + sucrose (■ ). Figure 8 shows water uptake in "growing up milk" powder with the addition of different ♦ calcium containing materials: powder matrix alone ( ) powder matrix with CaCI 2 · 2 H20 (·), powder matrix with co-crystalline Sucrose · CaCI 2 · 4 H20 (A), and powder matrix with the equivalent dry-mix CaCI 2 · 2 H20 + sucrose (■ ).
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