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Wo 2011/060944 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 _ . ... _ 26 May 2011 (26.05.2011) WO 2011/060944 A2 (51) International Patent Classification: (74) Agents: CARVAJAL Y URQUIJO, Isabel et al; A61K 9/16 (2006.01) A61K 9/50 (2006.01) Clarke, Modet & Co., C/Goya 11, 28001 Madrid (ES). A61K 9/48 (2006.01) (81) Designated States (unless otherwise indicated, for every (21) International Application Number: kind of national protection available): AE, AG, AL, AM, PCT/EP20 10/007024 AO, AT, AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, DO, (22) International Filing Date: DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, 19 November 2010 (19.1 1.2010) HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, (25) Filing Language: English KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, (26) Publication Langi English NO, NZ, OM, PE, PG, PH, PL, PT, RO, RS, RU, SC, SD, (30) Priority Data: SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, 200931026 20 November 2009 (20.1 1.2009) ES TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (71) Applicants (for all designated States except US): GP (84) Designated States (unless otherwise indicated, for every PHARM, S.A. [ES/ES]; Poligono Industrial Els Vinyets- kind of regional protection available): ARIPO (BW, GH, Els Fogars, Ctra. Comarcal 244, Km 22, E-08777 Sant GM, KE, LR, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, Quinti de Mediona (Barcelona) (ES). DEFIANTE FAR- ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, MD, RU, TJ, MACEUTICA, S.A. [PT/PT]; Rua dos Ferreiros, 260, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, ΓΓ Funchal - Madeira 9000 082 (PT). EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, , LT, LU, LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, (72) Inventor: CARMINATI, Paolo (deceased). SIN- SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GROSSI, Maria Gabriella (deceased). CARMINATI, GW, ML, MR, NE, SN, TD, TG). Silvia (deceased). CARMINATI, Giuseppe Paolo (de ceased). Published: — without international search report and to be republished (72) Inventor; and upon receipt of that report (Rule 48.2(g)) (75) Inventor/Applicant (for US only): PARENTE DUENA, Antonio [ES/ES]; Passeig Can Sagrera, 17-21, 08960 San Just Desvern - Barcelona (ES). < © o o (54) Title: ACTIVE PHARMACEUTICAL INGREDIENT CAPSULES AND POLYUNSATURATED FATTY ACID ESTERS (57) Abstract: Pharmaceutical composition in the form of a capsule which contains alkyl esters of polyunsaturated fatty acid (PUFA) and active pharmaceutical ingredients for the treatment and/or prevention of cardiovascular diseases and/or inflammatory processes. ACTIVE PHARMACEUTICAL INGREDIENT CAPSULES AND POLYUNSATURATED FATTY ACID ESTERS FIELD OF THE INVENTION This invention relates to a pharmaceutical composition in the form of a capsule which comprises a suspension of polymeric microcapsules suspended in an oil which contains alkyl esters of polyunsaturated fatty acids (PUFA), wherein the microcapsules contain at least one polymer and one active pharmaceutical ingredient, and its use for the treatment and/or prevention of cardiovascular diseases and/or inflammatory processes. BACKGROUND OF THE INVENTION Among the most used active pharmaceutical ingredients for the treatment of cardiovascular diseases are the calcium channel blockers or antagonists, beta blockers or beta-adrenergic antagonists, the platelet antiaggregants and/or anticoagulants. The main use of the calcium channel blockers in the treatment of angina pectoris, hypertension and cardiac dysrhythmia. Beta blockers are competitive antagonists of the beta-adrenergic receptors and are used for the treatment of cardiovascular disorders such as hypertension, angina pectoris, cardiac dysrhythmia, myocardial infarction and heart failure. Platelet antiaggregants reduce platelet aggregation and are used to prevent thromboembolic episodes in patients who have suffered a myocardial infarction, ischemic cerebral infarction or transitory ischemic attacks, unstable angina and for primary prevention of thromboembolic episodes in patients at risk. Some of them are used for the prevention of reocclusion or restenosis after an angioplasty or a coronary bypass. Anticoagulant drugs are used for the treatment and profilaxis of thromboembolic disorders. Non-steroidal anti-inflammatory drugs are drugs with analgesic and anti-inflammatory properties, of generalized use. The are particularly suitable for the treatment of illnesses or processes involving inflammation and/or pain, such as rheumatic disorders, among others. Polyunsaturated fatty acids (PUFA) also possess a known beneficial effect on the prevention of cardiovascular events and are often used in combination therapy in patients who have suffered some type of cardiovascular episode. There are numerous studies on anti-hypertensive, reduction of serum cholesterol, anti-hypertriglyceridemic, antiarrhythmic, antiplatelet and anti-inflammatory effects of PUFAs [Bucher H.C. e al. Am. J. Med. 112: 298-304 (2002); Benatti P. et al. J. Am. Coll. Nutr. 23: 281-302 (2004); Lee J.H. et al. Mayo Clin. Proc. 83: 324-332 (2008); Heinz R. Adv.Ther. 26: 675-690 (2009)]. PUFAs are essential fatty acids and should be obtained from a person's diet. They are divided into omega-3 and omega-6 fatty acids depending on the position of the first unsaturation (n-3 and n-6 respectively). The principal omega-3 fatty acids are found in fish oils, such as eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA). PUFAs can be found in the form of triglycerides or alkyl esters. Commercial compositions of omega-3 fatty acid alkyl esters vary in purity and content of fatty acids and are normally expressed in relation to the content in EPA and DHA. PUFAs, in any of their forms, are easily oxidized and should be stored under an inert atmosphere and protected from light. Commercial compositions contain antioxidants to minimize their degradation. The instability of many of the aforementioned active pharmaceutical ingredients is also known. The photolability of calcium channel blockers which possess a 1,4- dihydropyridine ring is known and there are numerous studies on its photostability in the literature. The dihydropyridine ring easily oxidizes and aromatizes to give a pyridine as a product of photodegradation. Amiodipine presents formulation problems due to the fact that it is hygroscopic and can degrade in the presence of moisture by a process of oxidation which leads to, among others, an impurity with the dihydropyridine ring aromatized to pyridine [WO 2008/062435 A2]. Amiodipine besylate is photosensitive and degrades both in solution and in solid state forming pyridine derivatives which lack therapeutic activity. The degradation studies show that amiodipine degrades slowly under heat stress, but it degrades quicker under photo-stress and even in acidic, alkaline and oxidative conditions, with the highest level of degradation in alkaline conditions [Aryal, S. et al. Acta Pharm. 58: 299-308 (2008)]. Another known pharmaceutical problem is that in solid pharmaceutical compositions of amiodipine besylate the mixtures of lactose, basic excipients (magnesium stearate) and water induce a certain instability in the amlodipine due to the Maillard reaction between the primary amino group and lactose [Abdoh, A. et al. Pharm. Dev. Technol. 9: 15-24 (2004)]. In a comparative study of photostability between amlodipine, nilvadipine and nifedipine, this latter active ingredient proved to be the most photosensitive. The photodegradation reactions involved include aromatization of the dihydropyridine ring and conversion of the nitro group of the benzene ring to nitroso group [Kawabe, Y. et al. J. Pharm. Biomed. Anal. 47: 618-624 (2008)]. The high photosensitivity of nifedipine makes necessary to protect it from the light during manufacturing, storage and handling of the pharmaceutical compositions [Aman, W . et al. Int. J. Pharm. 243: 33-41 (2002)]. US 4954346 A mentions the photosensivity of the commercial preparation of nifedipine in Procardia® soft gelatin capsules (or Adalat®); this patent proposes the improvement of the stability of these type of compositions by adding solubilizing agents such as cyclic carbonate diester to the liquid content of the capsule. Since these derivatives of dihydropyridine are instable due to oxidation catalyzed by light or heat or by the interaction with some excipients, there are limitations in the preparation of pharmaceutical compositions which contain them. As well as proposing the preparation of new amlodipine salts which are photochemically more stable [WO 2008/010659 A1], in EP 1813274 A 1 the photostabilization of the dihydropyridines by adding iron oxide and carrageenans is proposed, and in W O 2008/062435 A2 through the addition of polyols; other alternatives studied are, for example, the protection by forming inclusion complexes with cyclodextrins [Bayomi, M.A. et al. Int. J. Pharm. 243: 107-1 7 (2002)]. In the case of beta blockers, the presence of the secondary amino group in alpha position with relation to the hydroxyl group affords them chemical instability, due to possible interactions with the excipients. This represents a problem during their storage. Thus, the amino group of carvedilol, for example, can react with aldehyde or ester functional groups [WO 2005/051383 A1], and degrades in the presence of polyvinylpyrrolidone and moisture [Galanopoulou, O. er al. J. Pharm. Biomed. Anal. 48: 70-77 (2008)]. A study of the stability of atenolol with different common excipients in the pharmaceutical industry concludes that atenolol is incompatible with some of them, such as ascorbic acid, citric acid or butylated hydroxyanisole [Kumar, V. et al. J. Pharm. Biomed. Anal. 49: 880-888 (2009)]. The ester group of esmolol hydrochloride is unstable in aqueous medium due to its great susceptibility to hydrolytic degradation [EP 0403578 B1; EP 1368019 B1], therefore, the presence of water in the formulation should be avoided.
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