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Wo 2010/117346 A2 (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 14 October 2010 (14.10.2010) WO 2010/117346 A2 (51) International Patent Classification: AO, AT, AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, A61K 31/593 (2006.01) CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, (21) International Application Number: HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, PCT/TR20 10/000081 KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, (22) International Filing Date: ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, 9 April 2010 (09.04.2010) NO, NZ, OM, PE, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, (25) Filing Language: English TT, TZ, UA, UG, US, 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, 2009/02817 10 April 2009 (10.04.2009) TR GM, KE, LR, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, MD, RU, TJ, (72) Inventor; and TM), European (AT, BE, BG, CH, CY, CZ, DE, DK, EE, (71) Applicant : BILGIC, Mahmut [TR/TR]; Tozkoparan ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, Mah. General AIi Riza Gurcan Cad. Merter Is, Merkezi MC, MK, MT, NL, NO, PL, PT, RO, SE, SI, SK, SM, Bagimsiz Bolum No:2/8 Merter, 341 73 Istanbul (TR). TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG). (74) Agent: HATICE GULBEN YILMAZ KARLIDAG; Tozkoparan Mah. General AIi Riza Gurcan Cad. Merter Published: Is, Merkezi Bagimsiz Bolum No:2/6 Merter/Istanbul, — without international search report and to be republished 34173 (TR). 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: STABLE PHARMACEUTICAL COMPOSITIONS WITH HIGH BIOAVAILIBILITY (57) Abstract: The present invention relates to pharmaceutical compositions comprising an active agent alone or in combination with another active agent which is used for the treatment and/or prophylaxis of diseases and conditions associated with abnormal bone resorption and/or effective as a supplement. STABLE PHARMACEUTICAL COMPOSITIONS WITH HIGH BIOAVAILIBILITY Field of the Invention The present invention relates to pharmaceutical compositions comprising an active agent alone or in combination with another active agent which is used for the treatment and/or prophylaxis of diseases and conditions associated with abnormal bone resorption and/or effective as a supplement. Background of the Invention The present invention provides a pharmaceutical composition which is used for the treatment and/or prophylaxis of diseases and conditions associated with abnormal bone resorption and/or effective as a supplement The term "desired effect" as used herein, refers to this effect of the composition comprising a strontium compound alone or in combination with vitamin D. Strontium (Sr) is an earth-alkali metal that has high chemical reactivity. It was first discovered by Thomas Charles Hope in 1798. Strontium ranelate (Formula I) was first described in United States Patent application 5128367 (European Patent number 0415850 is also a member of the patent family). The process for the preparation of strontium ranelate and its use for the treatment of bone disorder, especially for osteoporosis, are described in this patent. Strontium is an element which has a high affinity to the bone tissue. Due to its high chemical and physical similarity to calcium, it can be used instead of calcium and can show the same activity. Its anti-osteoporotic effect is suggested to demonstrate itself with a dual mechanism of bone production improvement and bone resorption reduction. 89Sr is a radiopharmaceutical used for bone pain secondary to metastatic bone cancer. The strontium acts like calcium and is preferentially incorporated into bone at sites of increased osteogenesis. This localization focuses the radiation exposure on the cancerous lesion. 90Sr is used as radiotherapy in cancer treatment due to its beta emission and long half-life characteristics. Strontium ranelate being one of the strontium compounds is effective in bone growth, increasing bone density and lessening bone fractures and the use of granule form of strontium ranelate for oral suspension is approved in Europe. Vitamin D is a group of fat-soluble prohormones, the two major forms of which are vitamin D (or ergocalciferol) and vitamin D (or cholecalciferol). There are also D1, D4 and D5 forms. The term vitamin D also refers to these metabolites and other analogues of these substances. β Vitamin D3 is a vitamin D form with the chemical name (3 ,5Z,7E)-9,10-secocholesta- 5,7,10(19)-trien-3-ol (Formula II). Vitamin D3 is the form of vitamin D that is synthesized naturally in the body. It is synthesized in the skin from 7-dehydrocholesterol, a sterol present in the mammalian skin, under the action of ultraviolet light. Vitamin D3 can be obtained partially from animal products. Vitamin D3 is hydroxylated in the liver and kidney, and becomes calcitriol (1,25- dihydroxyvitamin D3). Calcitriol plays an important role in the maintenance of the calcium balance and the parathyroid hormone regulation. It stimulates the renal reabsorption of calcium, and increases the intestinal absorption of calcium and phosphorus and their mobilization from the bone to the plasma. It is believed that the absorption of calcium in the intestines is achieved by the calcitriol by binding to specific receptors in the cytoplasm of intestinal mucosa cells. Then calcium is absorbed by formation of a calcium binding protein. When calcium and phosphorus levels of plasma reach saturation, mineralization occurs in the bone. Vitamin D affects the absorption of strontium in the same way as it affects calcium absorption. Hence, Vitamin D can be added to a strontium composition to be used for the treatment and/or prophylaxis of diseases and conditions associated with abnormal bone resorption and/or as a supplement. The present invention relates to pharmaceutical compositions which are effective for the treatment and/or prophylaxis of diseases and conditions associated with abnormal bone resorption and/or as a supplement. The mentioned compositions comprise a strontium compound alone or in combination with vitamin D. The object of the invention is to provide a composition comprising the active agent or agents in a pharmaceutically acceptable, non-toxic and therapeutically effective amount according to the invention and the formulation of these active agent/agents to achieve this desired effect. However, a solubility problem arises with most of the pharmaceutical compositions comprising such a strontium compound. This solubility problem significantly affects the bioavailability of the drug, hence its efficiency. European Patent No. 1534305 describes the use of strontium malonate with a solubility of 1- 100 g/1 at room temperature, for prevention and/or treatment of various bone conditions. The divisional application of European Patent No. 1534305, European Application No. 1745791 describes the use of some strontium salts also with a solubility of 1-100 g/1 at room temperature, for prevention and/or treatment of various bone conditions. It has been indicated in these patents that these novel salts encounter no solubility problems. In the International Patent Application with publication number WO 2004/098617, controlled release compositions comprising at least one strontium salt in tablet form, which is suitable for administration once daily, are described. It has been indicated in this application that these tablets with altered release characteristics encountered no solubility problems. International Patent Application with publication number WO2007/003200 describes the method for synthesis of some strontium salts (strontium malonate, strontium-di-L-ascorbate, strontium fumarate, strontium salicylate, strontium succinate, strontium di-ibuprofenate and strontium maleate) from strontium carbonate, at low temperatures. It is stated in this application that strontium salts prepared with the mentioned method encountered no solubility problems. International Patent Application with publication number WO2007/003200 describes pharmaceutical compositions comprising at least two strontium salts (preferably strontium carbonate and strontium chloride). It is stated in this application that the mentioned pharmaceutical compositions comprising at least two strontium salts encountered no problems with solubility or bioavailability. As a result, some methods such as manufacturing of novel strontium salts with improved solubility to enhance the solubility of the strontium compounds, new manufacturing process to obtain these salts, invention of suitable salt combinations and altering the release characteristic of tablets which include these salts have been tried in the prior art. The course of preparation of novel salts with improved solubility and invention of suitable salt combinations require both time and capital, limiting appropriate salt forms. Thus the search for a better solution still continues. Finding a solution that would only cover the solubility problem is not preferred, since the enhancement of the release characteristics of tablet dosage form requires a complicated production
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