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WO 2015/195491 Al 23 December 2015 (23.12.2015) P O P C T

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WO 2015/195491 Al 23 December 2015 (23.12.2015) 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 2015/195491 Al 23 December 2015 (23.12.2015) P O P C T (51) International Patent Classification: (81) Designated States (unless otherwise indicated, for every C07F 3/02 (2006.01) C07F 3/04 (2006.01) kind of national protection available): AE, AG, AL, AM, A61K 31/7135 (2006.01) C07F 3/06 (2006.01) AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, A61K 33/00 (2006.01) BZ, 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, IR, IS, JP, KE, KG, KN, KP, KR, PCT/US2015/035686 KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, MG, (22) International Filing Date: MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, 12 June 2015 (12.06.2015) 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, (25) Filing Language: English TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (26) Publication Language: iglish ( ) Designated States (unless otherwise indicated, for every (30) Priority Data: kind of regional protection available): ARIPO (BW, GH, 62/013,904 18 June 2014 (18.06.2014) US GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, 62/058,491 1 October 2014 (01. 10.2014) us TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, (71) Applicant: THETIS PHARMACEUTICALS LLC DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, [US/US]; 167 Old Post Road, 2nd Floor, Southport, CT LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, 06890 (US). SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, KM, ML, MR, NE, SN, TD, TG). (72) Inventors: SCIAVOLINO, Frank, C ; 167 Old Post Road, 2nd Floor, Southport, CT 06890 (US). MATH IAS, Published: Gary; 167 Old Post Road, 2nd Floor, Southport, CT 06890 — with international search report (Art. 21(3)) (US). (74) Agents: LIBERTO, Muriel et al; Mintz Levin Cohn Fer ris, Glovsky and Popeo, P.C., Chrysler Center, 666 Third Avenue, New York, NY 10017 (US). (54) Title: MINERAL AMINO-ACID COMPLEXES OF ACTIVE AGENTS (I) ¾ HN i R H Λ (57) Abstract: The present invention provides compounds of Formula I and related compositions and methods. Formula (I). R i and R2each refer to a branched or unbranched carbon chain of from 1 to 20 carbons having at least one basic function; R i and R2 are the —- same or different; X i and X 2 are independently selected from H and -CO-Z, where Z is a peptide moiety incorporating from 1 to 5 amino acids, or a pharmaceutically acceptable salt thereof; X i and X 2are the same or different; M is a divalent metal cation selected from magnesium (Mg 2 +), calcium (Ca2+), and zinc (Zn +); A and B are each a molecule having at least one acidic function, either A or B, but not both, may be absent, and when both A and B are present, A and B may be the same or different. In a particular embodi- ment, at least one of "A" and "B" or both are fatty acids. A representative example of the application is the compound Magnesium Lysinate bis docosapentaenoic acid shown hereafter, Formula; The complexes of the application are intended for pharmaceutical compositions or as food additive, notably to treat conditions responsive to treatment with polyunsaturated fatty acids. MINERAL AMINO-ACID COMPLEXES OF ACTIVE AGENTS CROSS-REFERENCE TO RELATED APPLICATIONS [01] The current application claims priority to U.S. Provisional patent application serial number 62/013,904, filed on June 18, 2014 and entitled "Compositions and Methods Relating To Fatty Acid Derivatives of Metallic Amino-Acid Complexes," and U.S. Provisional patent application serial number 62/058,491, filed on October 1, 2014 and entitled "Mineral Amino- Acid Complexes of Therapeutic Agents," the contents of which are incorporated by reference herein in its entirety. FIELD OF THE INVENTION [02] The present invention relates to the field of drug delivery and particularly the use of mineral amino acid comprising salts of active agents and related compositions to deliver the active agents to a subject. BACKGROUND [03] Amino acid chelates for delivery of minerals to biological tissues are described in US 4,863,898 and US 4,599,152 (Albion). Amino acid chelates in this context refers to the product resulting from the reaction of a polypeptide, dipeptide or naturally occurring alpha amino acid with a metal ion having a valence of two or more to form a ring structure in which the positive electrical charges of the metal ion are neutralized by the electrons available through the carboxylate or free amino groups of the alpha amino acid. As described by US 4,863,898, chelate formation through neutralization of the positive charges of the divalent metal ions can be through the formation of ionic, covalent or coordinate covalent bonding. US 4,863,898 states that it provides an advantage over the prior art metal chelates, which are effective to increase metal content in biological tissues generally, by providing metal chelates targeted to specific tissues. Manganese, calcium, iron, magnesium, copper, and zinc amino acid chelates are among those described. [04] Polyunsaturated fatty acids of the omega-3 series ("omega-3 fatty acids") have shown a wide spectrum of biological activities suggesting their possible usefulness in treating a range of diseases and disorders including metabolic disorders, cardiovascular complications, inflammatory diseases, central nervous system disorders, and ophthalmic complications. There are three major types of omega-3 fatty acids involved in the human physiology: - linolenic acid (ALA; found in plant oils), eicosapentaenoic acid (EPA), and docosahexaenoic acid (DHA) (both commonly found in marine oils). Marine algae and phytoplankton are also sources of omega-3 fatty acids. Common sources of plant oils containing the omega-3 ALA fatty acid include walnut, edible seeds, clary sage seed oil, algal oil, flaxseed oil, Sacha Inchi oil, Echium oil, and hemp oil, while sources of animal omega-3 EPA and DHA fatty acids include fish oils, egg oil, squid oils, and krill oil. Often these primary omega-3 fatty acids are present with numerous minor omega-3 fatty acids as mixtures. But the poor aqueous solubility of omega-3 fatty acids limits their utility as therapeutic agents and as nutraceutical additives to food and drink due to a phenomenon referred to as solubility-limited absorption which limits the plasma levels that can be achieved following oral administration. In fact, the omega-3 fatty acids are essentially insoluble in water and both the free acid and sodium salt forms create soap-like emulsions when mixed with water. Thus, although omega-3 fatty acids are absorbed following oral administration, the relatively low plasma levels achieved cannot be increased simply by increasing the dose administered. [05] In addition to their poor aqueous solubility, omega-3 fatty acids suffer from susceptibility to lipid oxidation. This oxidation leads to formation of undesirable fishy and rancid off-flavors that render compositions comprising them less palatable. [06] WO 2 140 11895 describes fatty acid salts of eicosapentaenoic acid (EPA) with lysine or docosahexaenoic acid (DHA) or EPA with metformin, piperazine, and meglumine. [07] US 201 1237813 (Jost Chemical Co.) describes mineral co-salts of polyunsaturated fatty acids and a non-fatty acid co-anion formed as a precipitate. [08] WO 2004082402 (Novartis AG) describes a combination, such as a combined preparation or pharmaceutical or nutritional composition, respectively, which comprises at least one cis-polyunsaturated fatty acid, at least one amino acid, and optionally at least one diabetes medicine for simultaneous, separate or sequential use in the prevention, delay of progression or treatment of diseases, especially metabolic disorders and in particular type 2 diabetes. [09] There is a need to develop new compositions able to deliver omega-3 fatty acids at much higher plasma levels than is possible using the currently available free fatty acid, sodium salt, or ester forms, in order to fulfill the therapeutic and nutritional promise of these compounds and translate the many promising in vitro and cellular pharmacology observations into clinical and general health benefits. The present invention addresses these needs. SUMMARY OF THE INVENTION [10] The invention provides compounds of Formula I, including enantiomers, polymorphs, solvates, and hydrates thereof: Formula I wherein R i and R2 each refer to a branched or unbranched carbon chain of from 1to 20 carbons having at least one basic function; Ri and R2 are the same or different; X and X2 are independently selected from H and -CO-Z, where Z is a peptide moiety incorporating from 1 to 5 amino acids, or a pharmaceutically acceptable salt thereof; X i and X2 are the same or different; M is a divalent metal cation selected from magnesium (Mg +), calcium (Ca +), and zinc (Zn2+); A and B are each a molecule having at least one acid function, either A or B, but not both, may be absent, and when both A and B are present, A and B may be the same or different. [1 1] In one embodiment, the basic function of R and R2 is selected from a primary amine, a secondary amine, a tertiary amine, and a guanidine.
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