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Man Kann Hittautu Un Nouveauti MANKANN HITTAUTUUS009872850B2 UN NOUVEAUTI (12 ) United States Patent (10 ) Patent No. : US 9 ,872 , 850 B2 Rinsch et al. (45 ) Date of Patent: * Jan . 23 , 2018 (54 ) COMPOSITIONS AND METHODS FOR 2008 /0031862 A1 2 /2008 Ghosal IMPROVING MITOCHONDRIAL FUNCTION 2008 /0031979 A1 * 2 /2008 Saliou et al. .. .. .. 424 /729 2008 / 0039179 A1 2 /2008 Seelig et al. AND TREATING NEURODEGENERATIVE 2008 /0206275 AL 8 / 2008 Ramazanov et al. DISEASES AND COGNITIVE DISORDERS 2009 / 0246300 AL 10 / 2009 Swilling 2009 /0326057 Al 12 /2009 Seeram et al. ( 75 ) Inventors : Christopher Lawrence Rinsch , Morges 2010 / 0004334 AL 1 / 2010 Jouni et al. ( CH ) ; William Blanco - Bose , Lausanne 2010 /0021533 Al 1 / 2010 Mazed et al. (CH ) ; Bernard Schneider , Pully (CH ) ; 2010 / 0055247 Al 3 /2010 Tirrito Charles Thomas , Cheseaux -sur - Lausanne (CH ) ; Carmen FOREIGN PATENT DOCUMENTS Sandi, Bremblens (CH ) ; Johan CN 101301319 A 11/ 2008 Auwerx , Buchillon (CH ) ; Penelope EP 2033526 A1 3 / 2009 EP 2068864 A2 6 / 2009 Andreux , Lausanne (CH ) ; Richardus H02304080 A 12 / 1990 Houtkooper, Lausanne ( CH ); Eija JP 2008 - 503456 A 2 / 2008 Pirinen , Lausanne (CH ) ; Laurent JP 2010 - 280627 A 12 / 2010 Mouchiroud, Lausanne (CH ) ; David WO WO -00 / 15044 AL 3 /2000 Genoux, Lausanne ( CH ) WO WO -01 / 49281 A2 7 /2001 ( 73 ) Assignee : Amazentis SA , Ecublens (CH ) (Continued ) ( * ) Notice : Subject to any disclaimer , the term of this OTHER PUBLICATIONS patent is extended or adjusted under 35 Bialonska et al ., Urolithins, Intestinal Microbial Metabolites of U . S . C . 154 ( b ) by 110 days . Pomegranate Ellagitannins, Exhibit Potent Antioxidant Activity in a Cell - Based Assay , 2009 , J Agric . Food Chem , 57 : 10181 - 10186 . * This patent is subject to a terminal dis 2016 https :/ /www .nhlbi . nih .gov /health /health -topics / topics / athero claimer . sclerosis # .* Office Action from corresponding Colombian Patent Application (21 ) Appl. No. : 13 / 336 , 841 No . 12 - 172 . 849 dated Aug . 28 , 2014 . Office Action from corresponding Chinese Patent Application No. 201180067142 . 4 dated Jul. 3 , 2014 . (22 ) Filed : Dec . 23 , 2011 Larrosa , M . et al. , “ Ellagitannins , ellagic acid and vascular health ” , Molecular Aspects of Medicine, 31 (6 ): 513 -539 (Pergamon Press , (65 ) Prior Publication Data Oxford , Great Britain , Dec . 1 , 2010 ) . Viuda -Martos , M . et al ., “ Pomegranate and its Many Functional US 2012 /0164243 A1 Jun . 28 , 2012 Components as Related to Human Health : A Review ” , Comprehen sive Reviews in Food Science and Food Safety , 9 ( 6 ) :635 -654 (Oct . Related U . S . Application Data 22 , 2010 ) . International Search Report and Written Opinion from parent PCT (60 ) Provisional application No . 61/ 426 , 957 , filed on Dec. application PCT/ US2011 / 067229 dated Jul . 25 , 2012 . 23, 2010 . (Continued ) (51 ) Int. Ci. Primary Examiner — Terry A McKelvey A61K 31/ 366 ( 2006 .01 ) Assistant Examiner — Catheryne Chen A61K 36 / 185 ( 2006 .01 ) ( 74 ) Attorney , Agent, or Firm — Dana M . Gordon ; Foley A61K 31/ 7048 ( 2006 . 01 ) Hoag LLP A61K 9 / 00 ( 2006 . 01) A61K 31 / 352 ( 2006 . 01 ) (57 ) ABSTRACT A23L 33 / 105 ( 2016 .01 ) Provided are compositions comprising compounds or pre ( 52 ) U . S . CI. cursors to compounds which may be used for a variety of CPC . .. A61K 31 /366 (2013 . 01 ) ; A23L 33 / 105 therapeutic applications including , for example , treating (2016 .08 ) ; A61K 9 / 0014 ( 2013 .01 ) ; ACIK and / or preventing a disease or disorder related to reduced or 9 /0053 (2013 .01 ) ; A61K 9 /0056 (2013 .01 ) ; inadequate mitochondrial activity , including aging or stress , A61K 31 /352 ( 2013 .01 ) ; A61K 31 / 7048 diabetes , obesity , and neurodegenerative diseases. The com ( 2013 .01 ) ; A61K 36 / 185 ( 2013 .01 ) ; A23V pounds relate generally to urolithins and precursors thereof, 2002/ 00 ( 2013 .01 ) including but not limited to ellagitannins and urolithin A . In (58 ) Field of Classification Search certain embodiments the compositions are presented in or as None food products or nutritional supplements . These same com See application file for complete search history. pounds and compositions can also be used advantageously in generally healthy individuals to increase or maintain ( 56 ) References Cited metabolic rate , decrease percent body fat, increase or main U . S . PATENT DOCUMENTS tain muscle mass ,manage body weight, improve or maintain mental performance ( including memory ) , improve or main 6 , 133, 311 A 10 /2000 Bok et al . tain muscle performance , improve or maintain mood , and 6 , 440 , 436 B1 8 / 2002 Ghosal 2005 /0282781 A112 / 2005 Ghosal manage stress . 2007 /0184136 AL 8 / 2007 Aviram 46 Claims, 46 Drawing Sheets US 9 ,872 ,850 B2 Page 2 References Cited Lee , H . - J . et al ., " B -Secretase (BACE1 ) Inhibitors from ( 56 ) Sanguisorbae Radix ” , Arch . Pharm . Res ., 28 ( 7 ) :799 - 803 (Korea , 2005 ) . FOREIGN PATENT DOCUMENTS Rock et al ., " Consumption of wonderful variety pomegranate juice and extract by diabetic patients increases paraoxonase 1 association WO WO - 2005 /097106 AL 10 / 2005 with high -density lipoprotein and stimulates its catalytic activities , ” WO WO - 2006 / 127832 A2 11 /2006 J Agric Food Chem , 56 ( 18 ) : 8704 - 8713 (2008 ) . WO WO 2007 / 127263 A2 * 11 / 2007 Sumner et al ., " Effects of pomegranate juice consumption on WO WO - 2008 /016554 AL 2 /2008 myocardial perfusion in patients with coronary heart disease ," Am WO WO - 2009 / 031023 A2 3 / 2009 J Cardiol , 96 ( 6 ) : 810 - 814 (2005 ) . WO WO - 2009 / 153652 A2 12 / 2009 Cerda , et al. , “ Identification of Urolithin A as a metabolite produced WO WO - 2011/ 011721 A2 1 / 2011 by human colon microflora from ellagic acid and related com pounds, ” J Agric Food Chem , 53 ( 14 ): 5571 -5576 ( 2005 ) . Cerda , et al ., “ Pomegranate juice supplementation in a chronic OTHER PUBLICATIONS obstructive pulmonary disease : a 5 -week , randomized , double Larossa , M . et al ., “ Anti - inflammatory properties of a pomegranate blind , placebo -controlled trial, ” Eur J Clin Nutr, 60 : 245 - 253 extract and its metabolite urolithin - A in a colitis rat model and the ( 2006 ) . effect of colon inflammation on phenolic metabolism ” , Journal of Dell' agli , et al. , “ Ellagitannins of fruit rind of pomegranate ( Punica Nutritional Biochemistry , 21 :717 - 725 ( Elsevier Inc . , 2010 ) . granatum ) antagonize in vitro the host inflammatory response Seeram , N . P . et al , “ Pomegranate Ellagitannin -Derived Metabo mechanism involved in the onset of malaria ,” Malaria J, 9 : 208 lites Inhibit Prostate Cancer Growth and Localize to the Mouse ( 2010 ) . Prostate Gland ” , J . Agric . Food Chem ., 55 :7732 -7737 ( American Johanningsmeier et al ., “ Pomegranate as a functional food and Chemcal Society , USA , 2007 ) . nutraceutical source , ” Ann Rev Food Sci Technol, 2 : 181 - 201 Abstract of unexamined Japanese application No. JP2010 - 280627 ( 2010 ) . published Dec . 16 , 2010 . Kasimsetty , et al. , “ Colon cancer chemopreventive activities of Basu et al. , “ Pomegranate juice : A heart - healthy fruit juice , " Nutr pomegranate ellagitannins and Urolithins, " J Agric Food Chem , Rev, 67 ( 1 ) : 49 - 56 (2009 ) . 58 ( 4 ) : 2180 -2187 ( 2010 ) . Bhattacharyya et al. , “ Beneficial Effect of Processed Shilajit on Office Action from corresponding Mexican Patent Application No . Swimming Exercise Induced Impaired Energy Status of Mice ," MX / a / 2013 /007262 , dated Mar . 11 , 2016 . Pharmacologyonline , 1 : 817 -825 ( 2009 ) . Trombold , J . R . et al ., “ Ellagitannin Consumption Improves Bhattacharyya et al. , " Shilajit Dibezno - alpha - Pyrones: Mitochon Strength Recovery 2 - 3 d after Eccentric Exercise” , Medicine and dria Targeted Antioxidants ,” Pharmacologyonline, 2 : 690 -698 Science in Sports and Exercise , 42 :493 -498 ( American College of ( 2009 ) . Sports Medicine , Mar. 2010 ) . Esmaillzadeh et al. , “ Concentrated pomegranate juice improves Examination Report No . 2 dated Mar . 9 , 2016 from corresponding lipid profiles in diabetic patients with hyperlipidemia , " J Med Food , Australian patent application No. 2011348068 . 7 ( 3 ) : 305 - 308 ( 2004 ) . Espín et al. , “ Iberian pig as a model to clarify obscure points in the Hartman , R . E . et al. “ Pomegranate juice decreases amyloid load bioavailability and metabolism of ellagitannins in humans, " J Agric and improves behavior in a mouse model of Alzheimer ' s disease ” , Food Chem , 55 ( 25 ) : 10476 - 10485 ( 2007 ) . Neurobiology of Disease , 24 ( 3 ) :506 - 515 ( Elsevier Inc ., St. Louis , MO 2006 ). * cited by examiner U . S . Patent Jan . 23, 2018 Sheet 1 of 46 US 9 ,872 ,850 B2 Figure 7 Uroliin A (UA ) Bllacic Acid (LX ) o Tellimagrandin ( ) * **. .. * 67 Puniculawin ( PA ) Puicalin ( PB ) U . S . Patent Jan . 23, 2018 Sheet 2 of 46 US 9 ,872 , 850 B2 Figure 2 somethingwww and menetes or UD $ { "? versosemua tang deboleli . UA U . S . Patent Jan . 23 , 2018 Sheet 3 of 46 US 9 , 872 , 850 B2 Figtirge 3 ????? ; 3333333# : ? : :' 38 ? ? XXX Ba : 8 : ?? : : : : : : : : * 1 3 4 3 2 w???????????????? ????????????????????????????????????????????????????????????????????????????? . & its as : . 2:334 ???? ?????????? ; ? s{ { 4483 44 : :: : 48? 483 ???? ? 38 387 ???????????? ???? ?????????????? ??????????? ????? ?? » ?? ????? ,?????;# && > . .3 .3 ?????? . Asia$ $ U . S . 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