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(12) United States Patent (10) Patent No.: US 9,597,305 B2 Minatelli Et Al USO095973 05B2 (12) United States Patent (10) Patent No.: US 9,597,305 B2 Minatelli et al. (45) Date of Patent: *Mar. 21, 2017 (54) COMPOSITION AND METHOD TO (52) U.S. Cl. ALLEVATE JOINT PAN USINGA CPC ............ A61K 31/20 (2013.01); A61K 31/122 MIXTURE OF FISH OIL AND FISH OIL (2013.01); A61K 31/167 (2013.01); A61 K DERIVED, CHOLINE BASED, 3 1/202 (2013.01); A61 K3I/232 (2013.01); PHOSPHOLPD BOUND FATTY ACID A61 K3I/573 (2013.01); A61 K3I/616 MIXTURE INCLUDING (2013.01); A61 K3I/66 (2013.01); A61 K POLYUNSATURATED EPA AND DHA 3 1/728 (2013.01); A61K 35/612 (2013.01); A61K 36/00 (2013.01); A61K 36/286 (71) Applicant: U.S. NUTRACEUTICALS, LLC, (2013.01); A61K 36/30 (2013.01); A61K 38/39 Eustis, FL (US) (2013.01); A61K 45/06 (2013.01) (72) Inventors: John A. Minatelli, Mount Dora, FL (58) Field of Classification Search (US); W. Stephen Hill, Ocala, FL (US); CPC ..... ... A61K 31 f2O Rudi E.'' Moerck, Sanford,s FLs (US) s See application file for complete search history. (73) Assignee: U.S. NUTRACEUTICALS, LLC, (56) References Cited Eustis, FL (US) U.S. PATENT DOCUMENTS (*) Notice: Subject to any disclaimer, the term of this patent is extended or adjusted under 35 93. A E. All et al. U.S.C. 154(b) by 0 days. 6476.005 B1 1/2002 Petito et al. This patent is Subject to a terminal dis- s: R 1939: Radet claimer. 734463 B2 7/2007 Nielsen 7,247,752 B2 7/2007 Lockwood et al. (21) Appl. No.: 14/793,833 8,481,072 B2 7/2013 Minatelli et al. 8,507,757 B2 8, 2013 Minatelli et al. (22) Filed: Jul. 8, 2015 8,524,980 B2 9/2013 Minatelli et al. 8,557.275 B2 10/2013 Minatelli et al. (65) Prior PublicationO O Data 89629248,945.608 B2 2/2015 Minatelli et al. US 2015/0306132 A1 Oct. 29, 2015 SEFE 38 NRNA (Continued) Related U.S. Application Data FOREIGN PATENT DOCUMENTS (60) Division of application No. 14/022,638, filed on Sep. 10, 2013, now Pat. No. 9,216,164, which is a ES 1%; '98. continuation of application No. 14/018.593, filed on Sep. 5, 2013, now Pat. No. 9,028,814, which is a (Continued) continuation of application No. 13/079.238, filed on Apr. 4, 2011, now Pat. No. 8,557.275, which is a OTHER PUBLICATIONS continuation-in-part of application No. 12/840,372, Spi & 8 - filed on Jul. 21, 2010, now Pat. No. 8,481,072. piller et al., “Safety of an Astaxanthin-Rich Haematococcus Pluvialis Algal Extract: A Randomized Clinical Trial.” Journal of Medicinal Food, vol. 6, No. 1, 2003 pp. 51-56. (60) Provisional application No. 61/227,872, filed on Jul. (Continued) 23, 2009, provisional application No. 61/345,652, filed on May 18, 2010. Primary Examiner — Bin Shen (51) Int. Cl. (74) Attorney, Agent, or Firm — Allen, Dyer, Doppelt, A6 IK3I/728 (2006.01) Milbrath & Gilchrist, P.A. A6 IK 3L/20 (2006.01) A6 IK 3L/22 2006.O1 A6 IK 45/06 3:08: (57) ABSTRACT A6 IK3I/I67 (2006.01) Beneficial and synergistic effects for alleviating joint pain A6 IK 3L/202 (2006.01) and symptoms of osteoarthritis and/or rheumatoid arthritis A 6LX 3/573 (2006.01) have been found using a mixture of fish oil and fish oil A6 IK3I/66 (2006.01) derived, choline based, phospholipid bound fatty acid mix A6 IK 36/00 (2006.01) ture including polyunsaturated EPA and DHA either alone or A6 IK 35/62 (2015.01) in combination with other active constituents, including A6 IK 36/286 (2006.01) astaxanthin and polymeric hyaluronic acid or Sodium A6 IK 36/30 (2006.01) hyaluronate (hyaluronan) in an oral dosage form. A6 IK 3L/232 (2006.01) A6 IK3I/66 (2006.01) A6 IK 38/39 (2006.01) 14 Claims, No Drawings US 9,597,305 B2 Page 2 (56) References Cited McKee et al., “Hyaluronan Fragments Induced Nitric-Oxide Synthase in Murine Macrophages Through a Nuclear Factor kB U.S. PATENT DOCUMENTS Dependent Mechanism,” Journal of Biological Chemistry, vol. 272, No. 12, Mar. 21, 1997, pp. 8013-8018. 9,034,366 B2 5, 2015 Minatelli et al. Brown et al., “Turnover of Hyaluronan in Synovial Joints: Elimi 9,050,364 B2 6, 2015 Minatelli et al. nation of Labelled Hyaluronan from the Knee Joint of the Rabbit.” 2003/009 1652 A1 5/2003 Ishaq Experimental Physiology, 1991, No. 76, pp. 125-134. 2003/OO96794 A1 5, 2003 Niehoff 2004/0180025 A1 9/2004 Long et al. Serhan et al., “Resolution of Inflammation: State of the Art, Defi 2004/0180851 A1 9/2004 Long et al. nitions and Terms.” The FASEB Journal, vol. 21, Feb. 2007, pp. 2004/0234587 A1 11/2004 Sampalis 325-332, Serhan et al., “Resolution of Inflammation: State of the 2004/0241249 A1 12/2004 Sampalis Art, Definitions and Terms.' The FASEB Journal, vol. 21, Feb. 2006, OO78625 A1 4/2006 Rockway 2007, pp. 325-332. 2007/00988O8 A1 5/2007 Sampalis Moreland, “Intra-Articular Hyaluronan (Hyaluronic Acid) and 2007,0196894 A1 8, 2007 Sim et al. Hylans for the Treatment of Osteoarthritis: Mechanisms of Action.” 2007/027O376 A1 11/2007 Chandler University of Alabama at Birmingham, Arthritis Reasearch & 2008, OO14282 A1 1/2008 Long et al. Therapy, vol. 5, No. 2, Jan. 2003, pp. 54-67. 2008, OO38780 A1 2/2008 Stocks et al. Lee et al., “Hyaluronan: A Multifunctional, MegaDalton, Stealth 2008/O166779 A1 7/2008 Thomas et al. 2009 OO61067 A1 3/2009 Tilseth et al. Molecule.” Current Opinion in Cell Biology, 2000, pp. 581-586. 2009,0170808 A1 7/2009 Ling et al. Kalman et al., “Effect of a Natural Extract of Chicken Combs with 2009/O181114 A1 7/2009 Minatelli et al. a High Content of Hyaluronic Acid (Hyal-Joint(R) on Pain Relief 2009/O181127 A1 7/2009 Minatelli et al. and Quality of Life in Subjects with Knee Osteoarthritis: A Pilot 2009,0258081 A1 10/2009 Minatelli et al. Randomized Double-Blind Placebo-Controlled Trial.' Nutrition 2010.0143571 A1 6, 2010 Breivik Journal, Jan. 2008, pp. 1-9. 2010, O291053 A1 11/2010 Clayton et al. Necas et al., “Hyaluronic Acid (Hyaluronan): A Review.” 2011/O117207 A1 5, 2011 Minatelli et al. Veterinarni Medicina, vol. 53, 2008, pp. 397-411. 2011 0195061 A1 8, 2011 Minatelli et al. Nishimoto et al., “Effect of Chondroitin Sulfate and Hyaluronic 2011/02688.11 A1 11/2011 Minatelli et al. Acid on Gene Expression in a Three-Dimensional Culture of 2013,0059768 A1 3/2013 Hallaraker et al. Chondrocytes,” Journal of Bioscience and Bioengineering, vol. 100, 2014,0005267 A1 1/2014 Minatelli et al. No. 1, 2005, pp. 123-126. 2015,0182552 A1 7, 2015 Minatelli et al. Yamawaki et al., “Hyaluronan Receptors Involved in Cytokine Induction in Monocytes.” Glycobiology, vol. 19, No. 1, 2009, pp. FOREIGN PATENT DOCUMENTS 83-92. EP 1724357 11 2006 Lee et al., “Production of Astaxanthin by Haematococcus.” Chemi GB 2 103 088 2, 1983 cals from Microalgae, Ed. Zvi Cohen, Taylor and Francis, UK IN 201526 2, 2007 (1999), pp. 173-195. JP 2005521629 7/2005 Bjerkeng et al., “Bioavailability of all-E-astaxanthin and Z-isomers WO O3,O27267 4/2003 of Astaxanthin in Rainbow Trout (Oncorhynchus mykiss).” Aqua WO 2004/060388 9, 2004 culture, vol. 157, Issues 1-2, Nov. 1997, pp. 63-82; Abstract Only WO 2004,112776 12, 2004 (2 pages). WO 2011/06295.3 5, 2011 Yang et al., “Glioma-Associated Hyaluronan Induces Apoptosis in WO 2013,032333 3, 2013 Dendritic Cells via Inducible Nitric Oxide Synthase: Implications WO 2014/O13335 1, 2014 for the use of Dendritic Cells for Therapy of Gliomas,” Cancer Res., WO 2014/O14766 1, 2014 May 2002; 62(9):2583-91; Abstract Only (2 pages). Ghosh et al., "Potential Mechanism of Action of Intra-Articular OTHER PUBLICATIONS Hyaluronan Therapy in Osteoarthritis: Are the Effects of Molecular Weight Dependent?” Semin Arthritis Rheum.; Aug. 2002; 32(1): 10 37; Abstract Only (2 pages). Khanafari et al., “Extraction of Astaxanthin Esters From Shrimp Rooney et al., “Angiogenic Oligosaccharides of Hyaluronan Waste by Chemical and Microbial Methods.” Iran. J. Environ. Enhance the Production of Collagens by Endothelial Cells,” Journal Health. Sci. Eng., 2007. vol. 4, No. 2, pp. 93-98. of Cell Science; May 1993; 105 (Pt 1):213 218: Abstract Only (1 Nuno et al., “Effects of the Marine Microalgae Isochrysis Galbana page). and Nannochloropsis Oculata in Diabetic Rats.” Journal of Func Ruff et al., “Eggshell Membrane in the Treamtent of Pain and tional Foods, vol. 5, No. 1, Jan. 2013, pp. 106-115. Stiffness from Osteoarthritis of the Knee: A Randomized, Multi Deutsch, “Evaluation of the Effects of Naptune Krill Oil on Chronic center, Double-blind, Placebo Controlled Clinical Study,” Clinical Inflammation and Arthritic Symptoms,” Journal of the American Rheumatology, Aug. 2009; 28 (8):907 14: Abstract Only (1 page). College of Nutrition, vol. 26, No. 1, pp. 39-47 (2007). Schiedt et al., “Natural Occurrence of Enantiomeric and Meso Bunea et al., “Evaluation of the Effects of Neptune Krill Oil on the Astaxanthin, 5. Ex Wild Salmon (Salmo salar andOncorhynchus).” Clinical Course of Hyperlipidemia,” Alternative Medicine Review, Helv. Chim. Acta; 1981; 64(2):449-57: Abstract Only (1 page). vol. 9, No. 4, pp. 420-428 (2004). Jiang et al., “Hyaluronan in Tissue Injury and Repair, Annu Rev Lee et al., “Astaxanthin Inhibits Nitric Oxide Production and Cell Dev Biology; 2007: 23:435-61; Abstract Only (1 page).
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