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Particulate Comprising a Calcium-Containing Compound and a Sugar Alcohol

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Particulate Comprising a Calcium-Containing Compound and a Sugar Alcohol (19) TZZ_¥Z¥_T (11) EP 1 753 403 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: A61K 9/16 (2006.01) A61K 9/20 (2006.01) 13.08.2014 Bulletin 2014/33 A61K 33/06 (2006.01) (21) Application number: 05744248.5 (86) International application number: PCT/DK2005/000338 (22) Date of filing: 24.05.2005 (87) International publication number: WO 2005/115342 (08.12.2005 Gazette 2005/49) (54) PARTICULATE COMPRISING A CALCIUM-CONTAINING COMPOUND AND A SUGAR ALCOHOL PARTIKEL MIT EINER CALCIUMHALTIGEN VERBINDUNG UND EINEM ZUCKERALKOHOL PARTICULES COMPRENANT UN COMPOSE CONTENANT DU CALCIUM ET UN ALCOOL DE SUCRE (84) Designated Contracting States: • NIELSEN, Carsten Martini AT BE BG CH CY CZ DE DK EE ES FI FR GB GR DK-2860 Søborg (DK) HU IE IS IT LI LT LU MC NL PL PT RO SE SI SK TR • OLSEN, Peder Mohr Designated Extension States: DK-4970 Kirke Hyllinge (DK) AL BA HR MK YU • BERTELSEN, Poul, Egon Himmelev, DK-4000 Roskilde (DK) (30) Priority: 24.05.2004 DK 200400813 (74) Representative: Prusko, Carsten Dietmar et al (43) Date of publication of application: Zacco GmbH 21.02.2007 Bulletin 2007/08 Bayerstraße 83 80335 München (DE) (73) Proprietor: Takeda Nycomed AS 1385 Asker (NO) (56) References cited: WO-A-00/28973 WO-A-98/52541 (72) Inventors: FR-A- 2 717 387 US-A1- 2003 194 440 • MATHIESEN, Jacob US-B1- 6 475 510 DK-9500 Hobro (DK) Note: Within nine months of the publication of the mention of the grant of the European patent in the European Patent Bulletin, any person may give notice to the European Patent Office of opposition to that patent, in accordance with the Implementing Regulations. Notice of opposition shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 1 753 403 B1 Printed by Jouve, 75001 PARIS (FR) EP 1 753 403 B1 Description Field of the invention 5 [0001] The present invention relates to a particulate material and a solid dosage form notably tablets comprising a regularly shaped calcium-containing compound such as a calcium salt as a therapeutically and/or prophylactically active substance and a pharmaceutically acceptable sugar alcohol such as, e.g., sorbitol and/or isomalt that has a micro structure as evidenced by SEM. The invention also relates to a process for the preparation of the particulate material and solid dosage form. The process involves agglomeration of the calcium-containing compound and the pharmaceu- 10 tically acceptable sugar alcohol by means of roller compaction. The particulate material obtained by roller compaction is suitable for use in the further processing of the particulate material into e.g. tablets such as chewing tablets. [0002] The present invention is based on the findings that the result of an agglomeration process by which a calcium- containing compound is agglomerated depends on the particular shape of the calcium-containing compound and the micro structure of the material used as a binder in the agglomeration process. 15 Background [0003] Calcium is essential for a number of key functions in the body, both as ionized calcium and a calcium complex (Campell AK.Clin Sci 1987; 72:1-10). Cell behaviour and growth are regulated by calcium. In association with troponin, 20 calcium controls muscle contraction and relaxation (Ebashi S. Proc R Soc Lond 1980; 207:259-86). [0004] Calcium selected channels are a universal feature of the cell membrane and the electrical activity of nerve tissue and the discharge of neurosecretory granules are a function of the balance between intracellular and extra cellular calcium levels (Burgoyne RD. Biochim Biophys Acta 1984;779:201-16). The secretion of hormones and the activity of key enzymes and proteins are dependent on calcium. Finally calcium as a calcium phosphate complex confers rigidity 25 and strength on the skeleton (Boskey AL. Springer, 1988:171-26). Because bone contains over 99% of the total body calcium, skeletal calcium also serves as the major long-term calcium reservoir. [0005] Calcium salts such as, e.g., calcium carbonate is used as a source of calcium especially for patients suffering from or at risk of osteoporosis. Moreover, calcium carbonate is used as an acid-neutralizing agent in antacid tablets. [0006] Furthermore, calcium may have anticancer actions within the colon. Several preliminary studies have shown 30 high calcium diets or intake of calcium supplementation is associated with reduced colon rectal cancer. There is increasing evidence that calcium in combination with acetylsalicylic acid (ASA) and other non-steroidal anti-inflammatory drugs (NSAIDS) reduce the risk the risk of colorectal cancer. [0007] Recent research studies suggest that calcium might relieve premenstrual syndrome (PMS). Some researchers believe that disruptions in calcium regulation are an underlying factor in the development of PMS symptoms. In one 35 study, half the women of a 466 person group of pre-menopausal women from across the U.S. were tracked for three menstrual cycles and were given 1200 mg of calcium supplements daily throughout the cycle. The final results showed that 48% of the women who took placebo had PMS related symptoms. Only 30% of those receiving calcium tablet did. [0008] Calcium salts like e.g. calcium carbonate is used in tablets and due to the high dose of calcium required, such tablets are often in the form of chewable tablets. It is a challenge to formulate chewable tablets containing a calcium 40 salt, which tablets have a pleasant taste and an acceptable mouthfeel without the characteristic dominating taste or feeling of chalk. [0009] Furthermore, i) the high dose of calcium carbonate (normally 300-600 mg of elemental calcium twice daily, corresponding to 750 - 1500 mg of calcium carbonate twice dally), ii) the inherent poor properties of regular shaped calcium carbonate with respect to tabletting properties like compressibility, which accordingly calls for the need of adding 45 one or more pharmaceutically acceptable excipients in order to obtain a suitable compressibility, and iii) the extremely bad taste or mouthfeel of a calcium salt itself especially with respect to chalkiness make it very difficult to prepare a tablet that has a suitable small size, which is conveniently small for a patient. Sufficient taste masking is another major challenge when formulating chewable tablets. [0010] The present inventors have found an easy way for producing e.g. chewable tablets containing a physiologically 50 tolerable calcium-containing compound by using a granulate comprising agglomerates of the calcium-containing com- pound. The granulate is obtained without use of any solvent (e.g. water), but involves the technique of roller compaction of the calcium-containing compound to form agglomerates having suitable properties for further processing into a solid dosage form such as, e.g., tablets. [0011] EP 0 054 333 (Stauffer Chemical Company) describes a process of compacting fine particles of calcium phos- 55 phate by means of roller compacting to obtain a powder. The powder obtained has a larger bulk density than the starting material, which makes it suitable for use as an excipient in producing pharmaceutical tablets. In contrast to EP 0 054 333 the present invention does not employ roller compaction with the aim of increasing the bulk density of a pharma- ceutically acceptable excipient, but as a novel method for agglomeration, i.e. for building up agglomerates of particles 2 EP 1 753 403 B1 in order to increase the mean particle size to a size that is suitable for further processing of the material into e.g. tablets such as, e.g., chewable tablets that have an acceptable taste and/or mouthfeel. [0012] In US 6,475,510, in particular in example 6, granules comprising calcium carbonate together with a combination of a waxy material and a taste-masking agent, and xylitol as pharmaceutically acceptable excipient which are prepared 5 by roller compaction and further compressed into bite-dispersion tablets are disclosed. [0013] Previously it has been described that the quality of the calcium-containing compound as well as the method for preparation of a pharmaceutical composition containing the calcium-containing compound are of great importance in order to obtain acceptable taste and mouthfeel of a chewable tablet (WO 00/28973). In contrast to WO 00/28973 the method according to the invention does not employ a step of binding the particles together by a wet granulation process, 10 which means that the method according to the invention advantageously can be employed when it is desired to incorporate substances that are sensitive towards humidity. An example of such a substance is vitamin D that often is included together with a calcium salt in a pharmaceutically dosage form. The present invention provides a simple and cost- effective alternative method to obtain such a dosage form without the need of a step e.g. involving wet granulation. 15 Description of the invention [0014] It has surprisingly been found that roller compaction of a calcium-containing compound together with a phar- maceutically acceptable sugar alcohol that has binding properties improves the properties for pharmaceutical use of the compacts obtained thereby. 20 [0015] As mentioned above, in the present context the process of roller compacting of a powder is applied as an alternative method to known granulation or agglomeration methods, i.e. wet granulation or - when tablets are prepared - direct compression using dry binders. The present inventors have found that the process of roller compacting is a very mild method that does not destroy the possibility of obtaining products that have an acceptable mouthfeel and at the same time are without a dominating chalk-like taste or feel.
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