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(12) Patent Application Publication (10) Pub. No.: US 2014/0004215 A1 BROWNELL Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2014/0004215 A1 BROWNELL Et Al US 2014.0004215A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2014/0004215 A1 BROWNELL et al. (43) Pub. Date: Jan. 2, 2014 (54) COMPOSITIONS AND METHODS FOR Publication Classification MANAGING WEIGHT (51) Int. Cl. (71) Applicants: Unigen, Inc., Cheonan-si (KR); Unigen, A 6LX36/575 (2006.01) Inc., Seattle, WA (US) A61E36/53 (2006.01) (72) Inventors: Lidia Alfaro BROWNELL, Tacoma, A61E36/85 (2006.01) WA (US); Byong-Il CHOI, A61E36/37 (2006.01) Cheongwon-gun (KR); Brandon (52) U.S. Cl. CORNELIUSEN, Tenino, WA (US); CPC ............... A61K 36/575 (2013.01); A61K 36/37 Mei-Feng HONG, Lacey, WA (US); (2013.01); A61 K36/53 (2013.01); A61 K Eu-Jin HYUN, Cheonan-si (KR); Qi 36/185 (2013.01) JIA, Olympia, WA (US); Ping JLAO, USPC ........................................... 424/745; 424/769 Lacey, WA (US); Hyun-Jin KIM, Asan-si (KR); Mi-Ran KIM, Cheonan-si (KR); Tae-Woo KIM, Ulsan (KR): Bo-Su LEE, Pohang-si (KR); (57) ABSTRACT Young-Chul LEE, Daejeon (KR): Jeong-Bum NAM, Cheongwon-gun (KR); Mesfin YIMAN, Kent, WA (US); The present disclosure provides Diels-Alder adducts of chal Ji-Hye Hwang, Jecheon-si (KR): cone and prenylphenyl moieties capable of modulating the Mi-Sun OH, Cheonan-si (KR) activity of cannabinoid receptors, and to oligomers of flavan 3-ol capable of modulating fat absorption and storage. Such (73) Assignees: Unigen, Inc., Cheonan-si (KR); Diels-Alder adducts of chalcone and prenylphenyl moieties UNIGEN, INC., Seattle, WA (US) or oligomers of flavan-3-ol can optionally be used in combi (21) Appl. No.: 13/904,851 nation with other weight management agents, such as anorec (22) Filed: May 29, 2013 tic agents, a lipase inhibitors, other cannabinoid receptor modulators, psychotropic agents, insulin sensitizers, stimu Related U.S. Application Data lants, or satiety agents, as well as to methods of use thereof (60) Provisional application No. 61/652,807, filed on May Such as treating or preventing weight gain or obesity, promot 29, 2012, provisional application No. 61/783,729, ing weight loss, appetite Suppression, modifying Satiety, or filed on Mar. 14, 2013. the like. Patent Application Publication Jan. 2, 2014 Sheet 1 of 3 US 2014/0004215 A1 Week O Week Week 2 Week 3 Week 4 Week 5 Week 6 Week 7 Week 8 NC . FD ?t X 40mg/kgOristat Yerba Mate Magnolia100mg/kg X- 500mg/kg 500mg/kgMutamba Morus Rosemary 200mgikg 500mg/kg Fig. 1 Patent Application Publication Jan. 2, 2014 Sheet 2 of 3 US 2014/0004215 A1 Week O Week 1 Week 2 Week 3 Week 4 Week 5 Week 6 Week 7 Week 8 Fig. 2 Patent Application Publication Jan. 2, 2014 Sheet 3 of 3 US 2014/0004215 A1 s A9'709. 2->0gzgelz.108 - 182 66969. s ->6979vaz-5 G6'6092 c5 5 ->608/9 la Cd 3 699 OCZ S i. >gll 698 CN 25 7299.9A. s 9 - >99-'08g. 8 s 9A9977 2 is ->0Gv-6z. i5 E9EA9 d wa CN ->700 S le888.98 le S 8 g K S 33 Xe- w- ra o o O ne. Sueu US 2014/0004215 A1 Jan. 2, 2014 COMPOSITIONS AND METHODS FOR from a chemical library based on its inhibition of fatty acid MANAGING WEIGHT synthase, but was developed as a pancreatic triglyceride lipase inhibitor. But, orlistat has been placed on a list of drugs CROSS-REFERENCE TO RELATED having a potential signal of serious risk due to cases of liver APPLICATIONS toxicity, which has led to a change in the product labeling and 0001. This application claims the benefit under 35 U.S.C. the FDA is continuing to evaluate this issue to determine the S119(e) of U.S. Provisional Patent Application No. 61/652, need for any further regulatory action (see www.fda.gov/ 807, filed May 29, 2012, and U.S. Provisional Patent Appli Drugs/GuidanceComplianceRegulatory Information/Sur cation No. 61/783,729, filed Mar. 14, 2013, where these two veillance/Adverse DrugEffects/ucm 161063.htm). provisional applications are incorporated herein by reference 0009 From the foregoing, a need is apparent for improved in their entireties. compositions and methods for weight management. BACKGROUND BRIEF SUMMARY 0010. In brief, the present disclosure is directed to com 0002 1. Technical Field pounds and compositions useful for weight management and 0003. The present disclosure relates to compositions and related methods, including stereoisomers, pharmaceutically methods for weight management and, more particularly, to or nutraceutically acceptable salts, tautomers, glycosides and Diels-Alder adducts of chalcone and prenylphenyl moieties, prodrugs of the disclosed compounds. to oligomers of flavan-3-ol, or both, optionally in combina 0011. In certain embodiments, this disclosure provides a tion with other weight management agents, such as anorectic composition comprising a mixture of a Morus extract agents, a lipase inhibitors, cannabinoid receptor modulators, enriched for one or more Diels-Alder adducts of a chalcone psychotropic agents, insulin sensitizers, stimulants, or Satiety and a prenylphenyl moiety, a Magnolia extract, and a Yerba agents, as well as to methods of use thereof such as treating or mate extract. In further embodiments, this disclosure pro preventing weight gain or obesity, promoting weight loss, vides a composition comprising a mixture of a Morus extract appetite Suppression, modifying Satiety, or the like. enriched for Diels-Alder adducts of a chalcone and a pre 0004 2. Description of the Related Art nylphenyl moiety, a Magnolia extract, and a Mutamba 0005. Obesity is a food problem. In industrialized coun extract. In further embodiments, this disclosure provides a tries, affluence provides abundant and variable food items to composition comprising a mixture of a Morus extract the general public. Food, with the associated taste and olfac enriched for Diels-Alder adducts of a chalcone and a pre tory pleasures, is an indulgence, not just for basic Survival. As nylphenyl moiety, a Rosemary extract, and a Yerba mate a result, obesity and obesity-related health issues are increas eXtract. ing rapidly and there is a strong need for dietary Supplements 0012 Exemplary Diels-Alder adducts of a chalcone and a that help with weight control. The market size for food prenylphenyl moiety include compounds having a structure Supplements that decrease body weight is large and there are of Formula I or II: few effective products. 0006 For many years, Cannabis sativa (marijuana) has been known to stimulate food consumption through the action of its active component, delta-9-tetrahydrocannabinol (THC), an exogenous cannabinoid. This effect prompted research into its mechanism of action. The binding sites for THC were eventually cloned and named CB1 and CB2. These receptors belong to the G-protein coupled family character ized by seven trans-membrane loop domains. Both receptors belong to Go Subclass and signal by negatively regulating cyclic AMP levels. CB1 was also shown to activate potassium channels. CB2 receptor is present in immune cells and is not involved in regulation of food consumption. CB1, the can nabinoid receptor involved in feeding behavior, is widely expressed both in brain and peripheral tissues, including adi pose tissue, skeletal muscles, liver, and gastrointestinal (GI) tract. II 0007 Most of the published CB1 receptor antagonists might be better termed “inverse agonists' as they are capable of inhibiting constitutive activity of non-occupied CB1 recep tors. The major clinical indications for this group of com pounds are obesity and substance abuse. In the past, five CB1 compounds have been tested in clinical studies. They include Rimonabant (Sanofi-Aventis, launched in 2006), MK-0364 (Merck, Phase III), Surinabant and AVE-1625 (Sanofi-Aven tis, Phase II), and SLV-319 (Solvay, Phase II). Rimonabant (marketed as AcompliaR), RimoslimTM or ZimultiR) was the first selective CB1 antagonist discovered in 1994. It was approved in 37 countries, but it has since been withdrawn from obesity treatment due to neurological side effects. 0008 Another product on the market is tetrahydrolipstatin (orlistat, sold as Alli(R) or Xenical(R). Orlistat was identified US 2014/0004215 A1 Jan. 2, 2014 or a pharmaceutically or nutraceutically acceptable salt, tau Alder adducts of a chalcone and a prenylphenyl moiety can be tomer, glycoside or stereoisomer thereof, wherein the Sub obtained or enriched from certain plants or certain plant parts, stituents are as defined herein. Such as Morus alba root bark, and can be used as a cannab 0013. In another aspect, the present disclosure provides inoid receptor (e.g., CB1, CB2) modulator. Modulation of methods for managing weight. In certain embodiments, the cannabinoid receptor activity can be helpful in managing compositions of this disclosure can be used in methods for weight or diabetes. Exemplary weight management agents treating, preventing, or managing weight gain or obesity or for use with the Diels-Alder adducts of a chalcone and a excess weight, promoting or managing weight loss, appetite prenylphenyl moiety include anorectic agents, lipase inhibi Suppression, reducing food craving, reducing eating between tors, other cannabinoid receptor modulators, psychotropic meals and in the evening hours, modifying Satiety, modifying agents, insulin sensitizers, stimulants, satiety agents, or any fat uptake or fat absorption, increasing metabolism to pro combination thereof. Furthermore, the Diels-Alder adducts mote weight loss or prevent weight gain, maintaining body of a chalcone and a prenylphenyl moiety of the present dis weight, promoting fat burn, increasing lipolysis, reducing closure, as well as compositions thereof, can be used in meth body fat or fatty tissues, increasing muscle or lean body mass, ods to treat or prevent weight associated disorders. reducing hepato-steatosis, improving fatty liver, improving 0019. In the following description, certain specific details one or more liver NASH scores, enhancing fat metabolism, are set forth in order to provide a thorough understanding of reducing the release of pro-inflammatory adipokines, various embodiments of this disclosure.
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