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WO 2014/168736 A9 16 October 2014 (16.10.2014) P O P C T

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WO 2014/168736 A9 16 October 2014 (16.10.2014) P O P C T (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) CORRECTED VERSION (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date WO 2014/168736 A9 16 October 2014 (16.10.2014) P O P C T (51) International Patent Classification: (74) Agents: BERMAN, Richard J. et al; ARENT FOX, LLP, A61P 19/04 (2006.01) A61K 31/26 (2006.01) 1717 K Street, N.W., Washington, District of Columbia A61K 31/095 (2006.01) 20036-5342 (US). (21) International Application Number: (81) Designated States (unless otherwise indicated, for every PCT/US20 14/029976 kind of national protection available): AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, (22) Date: International Filing BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, 15 March 2014 (15.03.2014) DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, (25) Filing Language: English HN, HR, HU, ID, IL, IN, IR, IS, JP, KE, KG, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, (26) Publication Language: English MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, (30) Priority Data: OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, 61/794,417 15 March 2013 (15.03.2013) US SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, (71) Applicant: NUTRAMAX LABORATORIES, INC. ZW. [US/US]; 2208 Lakeside Boulevard, Edgewood, Maryland 21040 (US). (84) Designated States (unless otherwise indicated, for every kind of regional protection available): ARIPO (BW, GH, (72) Inventors: CORNBLATT, Brian; 637 Wyndswept Way, GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, SZ, TZ, Westminster, Maryland 2 1158 (US). BZHELYANSKY, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, TJ, Anton; 1101 N. Calvert St., Apt. 801, Baltimore, Maryland TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, 21202 (US). HENDERSON, Robert; 4325 Federal Hill EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, ΓΓ, LT, LU, LV, Road, Street, Maryland 2 1154 (US). HSU, Chia-Ping MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, Charles; 2909 Excelsior Springs Court, Ellicott City, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, Maryland 21042 (US). KM, ML, MR, NE, SN, TD, TG). Published: — with international search report (Art. 21(3)) [Continued on next page] (54) Title: SULFORAPHANE/SULFORAPHANE PRECURSOR AND PHYTOSTEROL/PHYTOSTANOL COMPOSITIONS FIG. 1 Conversion of Glucoraphanin at 38°C without Ascorbic Acid r < 00 Time, min (57) Abstract: The invention relates to the combination of a sulforaphane precursor, an enzyme capable of converting the o sulforaphane precursor to sulforaphane, an enzyme potentiator, and a phytosterol and/or phytostanol or ester thereof. The invention also relates to the combination of a sulforaphane or a derivative thereof and a phytosterol and/or phytostanol or ester thereof. The in - vention also relates to the combination of a broccoli extract or powder and a phytosterol and/or phytostanol or ester thereof. The in vention provides compositions and methods relating to these combinations. w o 2014/168736 A9 1I 11 II I 1 I1 II I III I llll II III III II (48) Date of publication of this corrected version: (15) Information about Correction: 13 November 2014 see Notice of 13 November 2014 SULFORAPHANE/SULFORAPHANE PRECURSOR AND PHYTOSTEROL/PHYTOSTANOL COMPOSITIONS CROSS-REFERENCE TO RELATED APPLICATION [0001] This application claims priority to the U.S. Provisional Patent Application No. 61/794,417, filed on March 15, 2013, which is incorporated by reference in its entirety. FIELD OF THE INVENTION [0002] The present invention relates to the combination of a sulforaphane precursor, an enzyme capable of converting the sulforaphane precursor to sulforaphane, an enzyme potentiator, and a phytosterol and/or phytostanol or an ester thereof. The present invention also relates to the combination of a sulforaphane or a derivative thereof and a phytosterol, phytostanol or an ester thereof. The present invention also relates to the combination of a broccoli extract or powder and a phytosterol and/or phytostanol or ester thereof. The present invention provides compositions and methods relating to these combinations. BACKGROUND OF THE INVENTION [0003] Connective tissue is the structural framework of cartilage, bone, synovium, ligament, meniscus, and tendon in articulating joints. Components of connective tissue are produced by resident cells and then secreted to form the extracellular matrix (ECM) characteristic of the tissue. In addition to serving as structural framework, the ECM also plays a critical role in cell communication and function. In articular cartilage, chondrocytes are aligned in a distinct pattern within the type II collagen ECM framework. Bone forming osteoblasts and osteocytes, as well as bone resorbing osteoclasts, are organized in mineralized type I collagen ECM. The few fibroblast-like and macrophage-like cells in the synovium are also held in place by ECM. Similarly, tenocytes and ligament cells are assembled together within the ECM. The synthesis and breakdown of connective tissue ECM is controlled by a network of regulatory molecules which are also produced by the resident tissue cells. This network includes growth factors and a wide array of molecules known as pro-inflammatory mediators. They include cytokines, chemokines, prostaglandins and nitric oxide. These molecules exhibit many biological activities. They can induce cell proliferation or cell death. These substances can also induce anabolic pathways for production of ECM or induce catabolic enzymes that can break down the ECM. Under physiological conditions, cell survival or death, the production or breakdown of connective tissue ECM is tightly controlled to maintain balanced homeostasis. The production and function of regulatory molecules is modulated by many factors including mechanical forces, physical factors such as temperature and pH, chemicals, microbes and their products. Under certain conditions, these factors can elicit excessive and untimely production of regulatory molecules leading to irreparable tissue damage, loss of function and death. [0004] Tissues react to mechanical, physical, chemical insults and infection by an inflammatory response. The inflammation process is known to lead to recovery, to healing, defense against infection and is usually life preserving. The inflammaiory response in humans and animals consists of two phases. The initial phase is characterized by the local synthesis of pro-inflammatory mediators such prostaglandins and leukotrienes. They are derived from arachidonic acid through the action of cyclooxygenases and lipoxygenases. These pro-inflammatory mediators increase local blood flow and enhance the permeability of endothelial cells to allow leukocyte recruitment and accumulation. Other pro-inflammatory mediators which are subsequently produced include cytokines ( L- β, TNF- α), chemokines (IL-8), and nitric oxide. In the second phase, the resolution phase, prostaglandins generated during the initial phase activate enzymatic pathways along which arachidonic acid is converted to chemical mediators with anti-inflammatory properties. It has been reported that prostaglandin E2 (PGE2) activates the expression of 15-lipoxygenase which generates anti-inflammatory lipoxins from arachidonic acid. Thus, the resolution of inflammation is driven by the pro-inflammatory response. Studies have revealed that the initiation, progression and termination of the inflammation process are tightly controlled. Prolonged, exaggerated inflammation has been associated with many disorders including osteoarthritis (OA), rheumatoid arthritis (RA), Alzheimer's disease, cardiovascular disease, and even cancer. [0005] In joint tissues, chondrocytes, synoviocytes, osteoblasts, osteoclasts, ligament cells, and tenocytes produce a wide array of pro-inflammatory mediators. Among these is prostaglandin E2 (PGE2), which is known to play a regulatory role by inducing the production of other mediators including cytokines, nitric oxide, and connective tissue degrading matrix metalloproteinase (MMP) enzymes. Due to its ability to induce MMPs, PGE2 contributes to the breakdown of cartilage ECM. In addition, PGE2 promotes bone resorption and osteophyte formation. PGE2 sensitizes nociceptors on peripheral nerve endings, thereby contributing to the development of inflammatory pain. PGE2 levels are locally regulated by the inducible cyclooxygenase-2 (COX-2) enzyme, a nitric oxide synthase in chondrocytes that inhibits cartilage and proteoglycan degradation. In pathologic conditions such as osteoarthritis, COX-2 expression is up-regulated with a concomitant increase in PGE2 production. [0006] The role of other tissues in the inflammation process is also well established. Inflammation of the synovial membrane is now recognized to be a key event in cartilage degradation in osteoarthritis, particularly during the early stages of the disease. Synovitis is characterized by activation of resident macrophage-like cells and fibroblast-like cells in the synovial membrane which leads to production of excessive amounts of pro-inflammatory mediators including TNF-alpha, IL-1 beta, and PGE2. Recent evidence suggests that synovial macrophages are the main source of the cytokines in the earliest stages of osteoarthritis and that they are important contributors to the cartilage damage in osteoarthritis throughout the course of the disease. Cytokines also induce production of PGE2 and active MMPs. It is now well accepted
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