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(12) United States Patent (10) Patent No.: US 9,724,313 B2 Skulachev (45) Date of Patent: Aug

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(12) United States Patent (10) Patent No.: US 9,724,313 B2 Skulachev (45) Date of Patent: Aug USOO9724313B2 (12) United States Patent (10) Patent No.: US 9,724,313 B2 Skulachev (45) Date of Patent: Aug. 8, 2017 (54) PHARMACEUTICAL COMPOSITION FOR Treatment of some ROS- and Age-related diseases (heart arrhyth USE IN MEDICAL AND VETERINARY mia, heart infarctions, kidney ischemia, and stroke), Biochemistry OPHTHALMIOLOGY (Moscow), 73(12): 1288-1299 and 1 figure. Clem et al. (2008) "Small-molecule inhibition of 6-phosphofructo (75) Inventor: Maxim V. Skulachev, Moscow (RU) 2-kinase activity Suppresses glycolytic flux and tumor growth.” Mol. Canc. Ther. 7(1): 110-120. Green (1974) “The electromechanochemical model for energy (73) Assignee: MITOTECH SA, Luxembourg (LU) coupling in mitochondria, Biochimica et Biophysica Acta, 346:27 78. (*) Notice: Subject to any disclaimer, the term of this Kirste et al. (1995) “Continuous-wave electron spin resonance patent is extended or adjusted under 35 studies of porphyrin and porphyrin-quinone triplet states,” J. Chem. U.S.C. 154(b) by 160 days. Soc. Perkin Trans. 2:2147-2152. Murphy et al. (2007) Targeting antioxidants to mitochondria by (21) Appl. No.: 13/315,397 conjugation to lipophilic cations. Annu. Rev. Pharmacol. Toxicol., 47:629-656. (22) Filed: Dec. 9, 2011 Plotnikov et al. (2008) “Interrelations of Mitochondrial Fragmen tation and Cell Death Under Ischemia/Reoxygenation and UV (65) Prior Publication Data Irradiation: Protective Effects of SkO1, Lithium Ions and Insulin.” FEBS Letters, 582:3117-3124. US 2012/0094.962 A1 Apr. 19, 2012 Plotnikov et al. (2010) “New-generation Skulachev ions exhibiting nephroprotective and neuroprotective properties.” Biochemistry Related U.S. Application Data (Mosc.), 75(2): 145-150. Skulachev et al. (2005) “Aging as mitochondria-mediated atavistic (63) Continuation-in-part of application No. program. Can aging be Switched off?” Ann. N.Y. Acad. Sci., PCT/RU2009/000295, filed on Jun. 10, 2009. 1057:145-164. Skulachev et al. (2009) “An attempt to prevent senescence: a (51) Int. Cl. mitochondrial approach,” Biochimica et Biophysica Acta. A6 IK 3L/20 (2006.01) 1787:437-461. A6 IK 3L/22 (2006.01) Smith et al. (2008) "Mitochondria-targeted antioxidants in the A6 IK 9/00 (2006.01) treatment of disease, 'Ann. N.Y. Acad. Sci., 1147:105-111. Snow et al. (2010) “A double-blind, placebo-controlled study to (52) U.S. Cl. assess the mitochondria-targeted antioxidant MitoC as a disease CPC .......... A61K 31/122 (2013.01); A61K 9/0048 modifying therapy in Parkinson's disease.” Mov. Disord. (2013.01) 25(11): 1670-1674. (58) Field of Classification Search Stefanova et al. (2010) “Behavioral effects induced by mitochon CPC ..... A61K 31/23: A61K 31/201: A61K 3 1/231 dria-targeted antioxidant SkO1 in Wistar and Senescence-acceler See application file for complete search history. ated OXYS rats,” J. Alzheimer's Dis. 21:479–491. Tauskela (2007) “MitoQ—a mitochondria-targeted antioxidant.” I (56) References Cited Drugs, 10:399-412. Triet et al. (1993) “Anxiogenic stimuli in the elevated plus-maze.” U.S. PATENT DOCUMENTS Pharmacol. Biochem. & Behay, 44:463-469. Antonenko, Yu, et al., Mitochondria-Targeted Plastoquinone 5,538,974 A 7/1996 Ogawa et al. Derivatives as Tools to Interrupt Execution of the Aging Program. 6,331,532 B1 12/2001 Murphy et al. 1. Cationic Plastoquinone Derivatives: Synthesis and in vitro Stud 7,109,189 B2 9/2006 Murphy et al. ies (2008), Biochemistry (Mosc.), 73 (12): 1273-1287. 2002fOO44913 A1 4/2002 Hamilton Doughan, et al., Original Research Communication: Mitochondrial 2005, OO65099 A1 3/2005 Walkinshaw et al. Redox Cycling of Mitoguinone Leads to Superoxide Production and 2007/0259908 A1 11/2007 Fujii et al. Cellular Apoptosis (2007), Antioxid. Redox Signal., 9(11):1825 2007/027O381 A1 11/2007 Murphy et al. 1836. 2008/O176929 A1 7/2008 Skulachev et al. 2008/0275005 A1 1 1/2008 Murphy et al. Neroev, et al., Mitochondria-Targeted Plastoquinone Derivatives as 2010/0273892 A1* 10, 2010 Miller et al. .................. 514,688 Tools to Interrupt Execution of the Aging Program. 4. Age-Related Eye Disease. SkQ1 Returns Vision to Blind Animals (2008), Bio FOREIGN PATENT DOCUMENTS chemistry (Mosc.), 73 (12): 1317-1328. (Continued) EP 1047701 B1 5, 2005 EP 1534,720 A1 6, 2005 Primary Examiner — Zohreh Fay EP 1321138 B1 4/2006 RU 2318500 C2 3, 2008 (74) Attorney, Agent, or Firm — Anne-Louise Kerner, WO 99.26582 A2 6, 1999 Morse, Barnes-Brown & Pendleton, P.C. WO 2004/O14927 A1 2, 2004 WO 2006/005,759 A2 1, 2006 (57) ABSTRACT WO 2007/046729 A1 4/2007 WO 2008048134 A1 4/2008 The invention relates to the manufacturing and use of WO 2009/005386 A1 1, 2009 pharmaceutical compositions of medicines (ophthalmic WO 2009/158348 A1 12/2009 preparations) comprising a mitochondria-addressed antioxi dant and a set of auxiliary Substances providing effective OTHER PUBLICATIONS treatment for ophtalmological diseases in humans and ani mals. Bakeeva et al. (2008) "Mitochondria-targeted plastoquinone deriva tives as tools to interrupt execution of the aging program. 2. 8 Claims, No Drawings US 9,724.313 B2 Page 2 (56) References Cited Reddy (2006) “Mitochondrial oxidative damage in aging and Alzheimer's disease: implications for mitochondrially targeted anti oxidant therapeutics,” J. Biomedicine and Biotech. Art.ID 31372:1- OTHER PUBLICATIONS 13. Skulachev, Clinical Review: How to Clean the Dirtiest Place in the Skulachev (2003) Aging and the programmed death phenomena, Cell: Cationic Antioxidants as Intramitochondrial ROS Scavengers Topics in Current Genetics, vol. 3, Nystrom and Osiewacz, Eds. (2005), IUBMB Life, 57(4/5):305-310. Model systems in Aging, Springer-Verlag Berlin Heidelberg 191 Skulachev, A Biochemical Approach to the Problem of Aging: 238. “Megaproject” on Membrane-Penetrating Ions. The First Results Starkov et al. (1997) “6-ketocholestanol is a recoupler for mito and Prospects (2007), Biochemistry (Mosc.), 72(2): 1385-1396. chondria, chromatophores and cytochrome oxidase International Search Report and Written Opinion of the Interna proteoliposomes.” Biochim. Biophys. Acta. 1318: 159-172. tional Searching Authority, PCT/RU2009/000295, 2/2512010, 7 Tompkins et al. (2006) “Mitochondrial dysfunction in cardiac pageS. ischemia-reperfusion injury: ROS from complex I, without inhibi PubChem compound CID 388445; Mar. 26, 2005 (Mar. 26, 2005) tion.” Dothan Biophys. Acta. 1762:223-231. retrieved from http://pubchem.ncbi.nlm.nih.gov/summary/sum Sidorova et al. (2004) “Transcriptional activation of cytochrome mary.cgi?cid=38845&loc=ec_rcs on Jul. 31, 2012 whole doc (4 P450 1A1 with alpha-tocopherol.” Bull Exp. Bio. Med., pages). 138(3):233-236. International Search Report and Written Opinion of the Interna Mecocci et al. (2000) “Plasma antioxidants and longevity: a study tional Searching Authority, PCT/US 12/40711, Aug. 20, 2012 (9 on healthy centenarians.” Free Radical Biology and Medicine, pages). 28(8): 1243-1248. Adlam et al. (2005) “Targeting an antioxidant to mitochondria Pozniakovsky et al. (2005) “Role of mitochondria in the phero decreases cardiac ischemia-reperfusion injury.” FASEB.J., 19:1088 mone- and amiodarone-induced programmed death of yeast.J. Cell 1095. Biol., 168(2):257-69. Agapova et al. (2008) "Mitochondria-Targeted Plastoquinone Orr et al. (2003) “Effects of overexpression of copper-zinc and Derivatives as Tools to Interrupt Execution of the Aging Program. manganese Superoxide dismutases, catalase, and thioredoxin 3. Inhibitory Effect of SkO1 on Tumor Development From p53 reductase genes on longevity in Drosophila melanogaster,” J. Biol. Deficient Cells,” Biochem. (Mosc). 73 (12): 1300-1316 (+ 3 fig. Chem., 278(29): 26418-26422. pages). Papp et al. (1999) “Glutathione status in retinopathy of prematu Anisimov (2007) “Molecular and Physiological Mechanisms of rity.” Free Radic. Biol. & Med., 27(7-8): 738-743. Aging.” Antioksidanty, Nov. 27, 2007, on line http://imguest. Petrosillo et al. (2005) “Mitochondrial dysfunction associated with alfaspace.net/BOOKMFMA/mfma 39 2.htm?embedded=yes cardiac ischemia reperfusion can be attenuated by oxygen tension translated from Russian to English. control. Role of oxygen-free radicals and cardiolipin, Biochimica Antonenko et al. (2008) "Protective effects of mitochondria-targeted et Biophysica Acta, 1710:78-86. antioxidant SkO in aqueous and lipid membrane environments,” J. Petrosillo et al. (2006) “Protective effect of melatonin against Membr. Biol., 222:141-149. mitochondrial dysfunction associated with cardiac ischemia Becker (2004) "New concepts in reactive oxygen species and reperfusion: role of cardiolipin.” FASEB J. 20:269-276. cardiovascular reperfusion physiology Cardiovascular Research, Sheu et al. (2006) "Targeting antioxidants to mitochondria: a new 61:461-470. therapeutic direction.” Biochimica et Biophysica Acta, 1762:256 Kasahara, et al. 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