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(12) United States Patent (10) Patent No.: US 9.271,949 B2 Hazan Et Al

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(12) United States Patent (10) Patent No.: US 9.271,949 B2 Hazan Et Al US00927 1949B2 (12) United States Patent (10) Patent No.: US 9.271,949 B2 Hazan et al. (45) Date of Patent: Mar. 1, 2016 (54) COMPOSITIONS COMPRISING ACIDIC 2005/023874O A1 10/2005 Fotinos EXTRACTS OF MASTC GUM 2009/004.8205 A1 2/2009 Meyer 2014/0294928 A1 10/2014 Hazan et al. (75) Inventors: Zadik Hazan, Zichron Yaakov (IL); Andre C. B. Lucassen, Rehovot (IL) FOREIGN PATENT DOCUMENTS CN 1173134 A 2, 1998 (73) Assignee: REGENERA PHARMA LTD., EP 152O585 4/2005 Rehovot (IL) GR 1.003541 3, 2001 GR 10O3868 4/2002 JP 2007135493 6, 2007 (*) Notice: Subject to any disclaimer, the term of this WO 01.21212 A1 3, 2001 patent is extended or adjusted under 35 WO O3,O92712 11, 2003 U.S.C. 154(b) by 0 days. WO O3,O97212 11, 2003 WO 2005/094837 10/2005 (21) Appl. No.: 13/821,194 WO 2005/112967 12/2005 WO 2006/OO3659 1, 2006 WO 20080243.74 A2 2, 2008 (22) PCT Filed: Sep. 7, 2011 WO 2010030082 A2 3, 2010 WO 2010/100650 9, 2010 (86). PCT No.: PCT/L2O11AOOO724 WO 2010/100651 9, 2010 S371 (c)(1), (2), (4) Date: Mar. 6, 2013 OTHER PUBLICATIONS (87) PCT Pub. No.: WO2012/032523 CAS Registry record for “Masticadienoic Acid' (retrieved Aug. 2014).* PCT Pub. Date: Mar. 15, 2012 Al-Habbal, M.J., Al-Habbal, Z, Huwez, F.U. A double-blind con trolled clinical trial of mastic and placebo in the treatment of (65) Prior Publication Data duodenal ulcer, Clin Exp Pharmacol Physiol, 1984, 11. (5), 541-4. Al-Said, M.S., Ageel, A.M., Parmar, N.S., Tariq M. Evaluation of US 2013/O17241.6 A1 Jul. 4, 2013 mastic, a crude drug obtained from Pistacia lentiscus for gastric and duodenal anti-ulcer activity, JEthnopharmacol, 1986, 15, (3), 271-8. Barra A. Coroneo V. Dessi S. Cabras P. Angioni A. Characterization Related U.S. Application Data of the Volatile Constituents in the Essential Oil of Pistacialentiscus L. (60) Provisional application No. 61/380,339, filed on Sep. from Different Origins and Its Antifungal and Antioxidant Activity, J 7, 2010. Agric Food Chem, 2007, 55, (17), 7093-7098. Bebb J.R., Bailey-FlitterN, Ala' Aldeen D, Atherton J.C., Mastic gum (51) Int. Cl. has no effect on Helicobacter pylori load in vivo, J Antimicrob A6 IK 36/22 (2006.01) Chemother, 2003, 52, (3). 522-523. A6 IK3I/9 (2006.01) Dietemann P. Edelmann M.J, Meisterhans C, Pfeiffer C, Zumbiihl S, Knochenmuss R. Zenobi R (2000) Artificial Photoaging of A 6LX3/57 (2006.01) Triterpenes Studied by Graphite-Assisted Laser Desorption/Ioniza (52) U.S. Cl. tion Mass Spectrometry. Helv Chim Acta 83: 1766. CPC ................. A61 K31/19 (2013.01); A61 K3I/57 Giner-Larza E.M., Máñez S. Giner R.M., Recio M.C., Prieto J.M., (2013.01); A61 K36/22 (2013.01); A61 K Cerda-Nicolás M. Rios J.L., Anti-inflammatory triterpenes from 2236/39 (2013.01) Pistacia terebinthus galls, Planta Med, 2002, 68, (4), 311-315. (58) Field of Classification Search Keisari Y. A colorimetric microtiter assay for the quantitation of None cytokine activity on adherent cells in tissue culture, JImmunol Meth See application file for complete search history. ods, 1992, 146, (2), 155-161. Loughlin M.F., Ala Aldeen D.A., Jenks P.J., Monotherapy with mas (56) References Cited tic does not eradicate Helicobacter pylon infection from mice, J Antimicrob Chemother, 2003, 51, (2), 367-371. U.S. PATENT DOCUMENTS (Continued) 4,713,243 A 12/1987 Schiraldi 5,637.290 A 6, 1997 Sodis et al. 5.948,430 A 9, 1999 Zerbe Primary Examiner — Theodore R West 6,074,688 A 6, 2000 Pletcher (74) Attorney, Agent, or Firm — Rothwell, Figg, Ernst & 6,177,096 B1 1/2001 Zerbe 6,207403 B1 3, 2001 Goldstein et al. Manbeck, P.C. 6,284.264 B1 9, 2001 Zerbe 6,319,541 B1 1 1/2001 Pletcher 6,592,887 B2 7, 2003 Zerbe (57) ABSTRACT 6,623,728 B2 9, 2003 Harichian et al. 6,709,671 B2 3, 2004 Zerbe The invention relates to compositions and formulations com 6,811,769 B2 11/2004 Watanabe prising isolated acidic fraction of mastic gum and uses thereof 7,048,943 B2 5, 2006 Barenholz 7,268,124 B2 9, 2007 Wiemer et al. for treating impaired neurological functions as well as wound 7,294,651 B2 11/2007 Syverson et al. and tissue repair. 7,358,377 B2 4/2008 Wiemer et al. 8,722,105 B2 * 5/2014 Hazan et al. .................. 424,725 8,956,601 B2 2/2015 Hazan 14 Claims, 27 Drawing Sheets US 9,271,949 B2 Page 2 (56) References Cited Atmani et al., (2009) Antioxidant capacity and phenol content of selected Algerian medicinal plants. Food Chem 112 (2): 303-309. OTHER PUBLICATIONS Boudsocq et al., (2005) Modulation of cellular response to cisplatin by a novel inhibitor of DNA polymerase beta. Mol Pharmacol 67(5): Marner F.J., Freyer A. Lex J. Triterpenoids from gum mastic, the resin 1485-92. of Pistacia lentiscus, Phytochemistry, 1991, 30, (11), 3709-3712. Marone P. Bono L. Leone E. Bona S, Carretto E. Perversi L., Bacte Chávez et al., (2005) Cytotoxic activity and effect on nitric oxide ricidal activity of Pistacia lentiscus mastic gum against Helicobacter production of tirucallane-type triterpenes. J Pharm Pharmacol 57(9): pylori, J Chemother 2001, 13, (6), 611-4. 1087-91. Paraschos S. Magiatis P. Mitakou S, Petraki K. Kalliaropoulos A. Dietemann et al., (2005) Chios gum mastic freshly harvested vs. Maragkoudakis P. Mentis A. Sgouras D. Skaltsounis A.L.. In Vitro commercial resin and its implications to aging of varnishes, and In Vivo Activities of Chios Mastic Gum Extracts and Constitu Zeitschrift fur Kunsttechnologie and Konservierung 19: 119-130. ents against Helicobacter pylori, Antimicrob Agents Chemother, 2007, 51, (2), 551-559. Kaliora et al., (2004) Detection and Identification of Simple Pheno Van den Berg K. J., Van der Horst J. Boon J.J., Sudeijer O.O., lics in Pistacia lentiscus Resin. Journal of Liquid Chromatography & Cis-1,4-poly-8-myrcene; the structure of the polymeric fraction of Related Technologies 27(2): 289-300. mastic resin (Pistacia lentiscus L.) elucidated, Tetrahedron Letters, Ljungman (2009) Targeting the DNA Damage Response in Cancer. 1998, 39, (17), 2645-2648. Chem Rev 109 (7): 2929-2950. Andrikopoulos et al., (2003) Biological activity of some naturally Olivera Ortega et al., (1999) Phytochemical study of cuachalalate occurring resins, gums and pigments against in vitro LDL oxidation. (Amphiptherygium adstringens, Schiede ex Schlecht). J Phytother Res 17(5): 501-507. Ethnopharmacol 68(1-3): 109-13. Barton and Seoane (1956) 801. Triterpenoids. Part XXII. The con Oviedo-Chávez et al., (2004) Principles of the bark of stitution and stereochemistry of masticadienonic acid. J Chem Soc Amphipterygium adstringens (Julianaceae) with anti-inflammatory 1956: 4150-4157. activity. Phytomedicine 11(5): 436-45. Mansouri et al., (2005) The effect of Pistacia vera L. gum extract on oxidative damage during experimental cerebral ischemia-reperfu Papageorgiou et al., (1997) Gas chromatographic mass spectro sion in rats. Iranian Biomedical Journal 9(4): 181-185. scopic analysis of the acidic triterpenic fraction of mastic gum. Jour Modugno et al., (2006) Chemical study of triterpenoid resinous mate nal of Chromatography A769(2): 263-273. rials in archaeological findings by means of direct exposure electron Sharifiand Hazell (2009) Fractionation of Mastic Gum in Relation to ionisation mass spectrometry and gas chromatography/mass spec Antimicrobial Activity. Pharmaceuticals 2: 2-10. trometry. Rapid Commun Mass Spectrom 20011): 1787-1800. Yueqin et al., (2003) Isolation of two triterpenoids and a biflavanone Arrieta et al., (2003) Purification of gastroprotective triterpenoids with anti-Inflammatory activity from Schinus molle fruits. Planta from the stem bark of Amphipterygium adstringens; role of Med 69(10): 893-8. prostaglandins, Sulfhydryls, nitric oxide and capsaicin-sensitive neu rons. Planta Med 69(10): 905-9. * cited by examiner U.S. Patent Mar. 1, 2016 Sheet 1 of 27 US 9,271,949 B2 1 OOOOOO S D. 50 OOOO –5OOOOO 1 O.O 2O.O 3OO 4O.O 5OO 6O.O 5. O 150 25. O 35. O 45. O 55. O 65. O RETENTION TIME MIN) FIG1 U.S. Patent Mar. 1, 2016 Sheet 2 of 27 US 9,271,949 B2 PE 300 601 SpVDD 727 1: TOF MS ES TIC 1 OO 6.09 |7.43 667e 4 y - 6.17 O.24 % 6.85 6.60 TIME ("o"200"; "Ab" it "Go",it it it trim"oo" It litti I, it "loo"It trimit FIG2A U.S. Patent Mar. 1, 2016 Sheet 3 of 27 US 9.271,949 B2 PE-300-601 spVDD 490(7.426)Cm (486:492) 1 TOF MS ES 4,81 e4 O 852 7 200 400 600 800 000 1200 PE 300-601 spVDD 480(7.273)Cm (478:483) 1 TOF MS ES 100 90 461 e4 200 400 600 800 000 1200 PE 300-601 spVDD 407(6.170) cm (405:409) TOf MSES1.83 e4 100 % 1164. O -la-ladula-ahoalhalaa-ur-wagola .k.a. 142)) (1272 1536 200 400 600 800 1000 1200 PE 300-601 SpVDD 401(6,085)Cm (400:404) 1 TOF MS ES 100 90 2.81e4 200 400 600 800 1000 1200 PE 300-601 spVDD 388 (5.889)Cm (385:390) 1 TOF MS ES 8,88e3 4....(1991 -). S. C997. 1165 22 198', 200 400 600 800 1000 200 7 U.S. Patent Mar. 1, 2016 Sheet 4 of 27 US 9,271,949 B2 PE 300-603 SpVDD 402(6.099)Cm (399.406) 1 TOF MS ES 100 910) 8.86e 4 455 911 437 / % -456 -912 409 391,\ 177 343) 10.
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