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US 20150246087A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2015/0246087 A1 Hazan et al. (43) Pub. Date: Sep. 3, 2015 (54) EXTRACTS AND THERAPEUTIC USES Publication Classification THEREOF (51) Int. Cl. (75) Inventors: Zadik Hazan, Zikron Yaakov (IL); A61E36/4 (2006.01) Andre C.B. Lucassen, Rehovot (IL) (52) U.S. Cl. CPC ............. A61K 36/14 (2013.01); A61 K 2.236/39 (73) Assignee: REGENERA PHARMA LTD., (2013.01) Rehovot (IL) (21) Appl. No.: 14/.407,049 (57) ABSTRACT The invention relates to compositions and formulations com (22) PCT Filed: Jun. 11, 2012 prising isolated fractions derived from Cupressaceae plant (86). PCT No.: PCT/L2012/OOO232 material. More particularly, the invention relates to pharma ceutical compositions comprising an isolated fraction of S371 (c)(1), Cupressaceae in a carrier and use thereof for treating fibrotic (2), (4) Date: May 12, 2015 conditions and neurodegenerative disorders. Patent Application Publication Sep. 3, 2015 Sheet 1 of 26 US 2015/0246087 A1 s N e 3 i s Wr AqSueu Patent Application Publication Sep. 3, 2015 Sheet 2 of 26 US 2015/0246087 A1 9. e 5 r S. i 3 y Ar ASUequ Patent Application Publication Sep. 3, 2015 Sheet 3 of 26 US 2015/0246087 A1 Figure 10 Pump #1 Initial Condition Pump Mode PG Flow 1.000 mL/min Max. Pressure 25.0 MPa) Min. Pressure 0.0 MPa. Solvents A 50.0% B 0.0% C 50.0%) D 0.0% Time Program # Time min Function value #1 value #2 value #3 value #4 1 1000 composition: 500 oo 500 00 2 1500 composition 340 oo 660 oo 3 1800 composition 340 00 660 00 4 2000 composition: 300 oo 700 oo 5 2500 composition 300 00 700 00 6 5000 composition a 100 oo oo 7 5500 composition a 00 00 1000 00 8 7000 composition 00 oo 1000 oo 9 71.00 composition. 500 00 500 00 to 7800 composition: 500 oo 500 oo Patent Application Publication Sep. 3, 2015 Sheet 4 of 26 US 2015/0246087 A1 s s 3 3 S e c C ad i s cm w ArtAsue Patent Application Publication Sep. 3, 2015 Sheet 5 of 26 US 2015/0246087 A1 o s N. - o o co o cas Lasal C s V c o e N C d A w w 19 p C d va Wri Asueu Patent Application Publication Sep. 3, 2015 Sheet 6 of 26 US 2015/0246087 A1 C Cd N C C. co c O am C Od w C O y N d C N s a c o vu w () Sp O O Wrd Asueu Patent Application Publication Sep. 3, 2015 Sheet 7 of 26 US 2015/0246087 A1 i A Sueu Patent Application Publication Sep. 3, 2015 Sheet 8 of 26 US 2015/0246087 A1 d c N 4. - C 8 s-e-ERO 3 - -i- C X o v - an O o s co o Ru M r ... ed c N ... ." c se vu g) c s o p o Wri Asueu Patent Application Publication Sep. 3, 2015 Sheet 9 of 26 US 2015/0246087 A1 i 3 v Wr Asue Patent Application Publication Sep. 3, 2015 Sheet 10 of 26 US 2015/0246087 A1 eue Geun-y i ---E.=sma-am s s i 3 Wr Asueu Patent Application Publication Sep. 3, 2015 Sheet 11 of 26 US 2015/0246087 A1 s s euleleun-W electeur-W i Asueu Patent Application Publication Sep. 3, 2015 Sheet 12 of 26 US 2015/0246087 A1 Figure 2A Figure2B Figure 2C Patent Application Publication Sep. 3, 2015 Sheet 13 of 26 US 2015/0246087 A1 Figure 3A Figure 3B Patent Application Publication Sep. 3, 2015 Sheet 14 of 26 US 2015/0246087 A1 s r s . R N exege Ng to-Auxoxa K. o nf se o o eleco N on as am so it E. wa C F nea 55a 'X Y reco e N ascene so r coal year an d seen A st y se r wo c d - s o i s A. ASueu Patent Application Publication Sep. 3, 2015 Sheet 15 of 26 US 2015/0246087 A1 Figure 5A Figure 5B : : Patent Application Publication Sep. 3, 2015 Sheet 16 of 26 US 2015/0246087 A1 Figure 6B Patent Application Publication Sep. 3, 2015 Sheet 17 of 26 US 2015/0246087 A1 udd UUO/ZH „ae^S\,ANÈ=~,, | V,9.In??? Patent Application Publication Sep. 3, 2015 Sheet 18 of 26 US 2015/0246087 A1 Patent Application Publication Sep. 3, 2015 Sheet 19 of 26 US 2015/0246087 A1 Figure 8 Patent Application Publication Sep. 3, 2015 Sheet 20 of 26 US 2015/0246087 A1 C s: s: O> 5 4. 1. ; t () o s o V i Ouluo uoy. AboxOOAO % Patent Application Publication Sep. 3, 2015 Sheet 21 of 26 US 2015/0246087 A1 de Y U Ce v& 52. O o gH H KX-CO 1-HH Hé O O O u s O C9 to E O GN O ve O w CD O O O O O. O. O. O. O. O. O. O. O O2 Caog o O N to Lo N et N V V V ver OLuoy% eunsolo deso Patent Application Publication Sep. 3, 2015 Sheet 22 of 26 US 2015/0246087 A1 Patent Application Publication Sep. 3, 2015 Sheet 23 of 26 US 2015/0246087 A1 Patent Application Publication Sep. 3, 2015 Sheet 24 of 26 US 2015/0246087 A1 : s i Patent Application Publication Sep. 3, 2015 Sheet 25 of 26 US 2015/0246087 A1 s Patent Application Publication Sep. 3, 2015 Sheet 26 of 26 US 2015/0246087 A1 S Q9N : 5 CO 8. N vs. Q9 ON US 2015/0246087 A1 Sep. 3, 2015 EXTRACTS AND THERAPEUTIC USES further comprising a specified proportion of a plant extract or THEREOF plant oil from Cupressaceae, and use thereof for treating psoriasis, blistery tinea, eczema, itch, shingles, chronic pru FIELD OF THE INVENTION ritus, pustulosis palmaris et plantaris, fungal tinea pedis and 0001. The invention relates to extracts of Cupressaceae malignant intumescence. products, including resins, and therapeutic uses thereof. More 0012 Methanolic extracts of certain Juniperus species particularly, the invention provides isolated fractions of have been disclosed to exhibit anti-inflammatory and anti Cupressaceae and compositions comprising Such fractions as nociceptive activities (Akkol et al., JEthnopharmacol. 2009 the pharmaceutically active ingredient. Sep. 7: 125(2):330-6). (0013 WO 2002/047707 discloses a method for inhibiting BACKGROUND OF THE INVENTION COX-2 activity, comprising administering a composition comprising an organic extract of a non-edible plant, wherein 0002 Essential oils and extracts derived from gymno the plant may be from the order Coniferales; and use of said sperms of the family Cupressaceae (cypress trees) have been extract for treating or preventing COX-2 mediated inflamma disclosed to have a wide range of therapeutic activities. Such tion or an inflammation-associated disorder, interalia arthri as that directed against various infectious agents. For tis, cancer, or a central nervous system disorder Such as example, anti-fungal activity of essential oils from Thuja Alzheimer's Disease. According to the disclosure, the extract Sutchuenensis (Lei et al., Nat Prod Commun. 2010 October; may be obtained using hydrocarbon Solvents, ether solvents, 5(10): 1673-6); antimicrobial activity of essential oils from chlorinated solvents, acetone, ethyl acetate, butanol, ethanol, cabreuva (Myrocarpus fastigiatus), cedarwood (Juniperus methanol, isopropyl alcohol and mixtures thereof. ashei), and juniper (Juniperus communis L. and Juniperus phoenicea) (Wanner et al., Nat Prod Commun. 2010 Septem 0014 Systematic investigations into the constituents of ber; 5(9): 1359-64; Ennajar et al., J Food Sci. 2009 Septem different Cupressaceae extracts have been reported (see for ber: 74(7):M364-71); and anti-HIV-1 activity of ethanol example, Enzell, Acta Chem. Sc. 1961, 15, 1303-12). extracts from Cupressus sempervirens, have been reported 00.15 Various terpene and terpenoid compounds have (Iran. J. Basic Med. Sc. Vol. 12 (3-4), 133-39, 2009). been extracted from leaves, bark, wood, roots and twigs of 0003 KR 20030033722 discloses a natural insecticidal Cupressaceae family members. Essential oils derived from composition containing an oil extracted from Cupressus semi Such plant parts have been disclosed to consist mainly of pervirens. monoterpenes and sesquiterpenes Such as C-pinene, 0004 JP 8169839 discloses a tar- and acid-free resin oil B-pinene, Sabinene, limonene, bisabolol, cedrene, farnesol, extract from Chamacyparis Spach and Thuiopsis dollabrata, longifolene and cadinene (see for example, Ennajar et al., J said extract having anti-bacterial and anti-mite activities, and Food Sci. 2009 September: 74(7):M364-71). Diterpene additional beneficial effects such as wound healing, promot derivatives isolated from non-volatile extracts include for ing epithelialization, and improving blood circulation. example sempervirol, totarol, ferruginol, manool, and toru 0005 WO98/051319 discloses a pharmaceutical compo solol (Piovetti et al. Phytochem. 19, 1980,2772-3). Triterpe sition comprising a mixture of Angelica oil from Angelica noids termed chamaecydines were disclosed as having been archangelica L., Umbelliferae and Red Cedar oil from Juni isolated from Chamaecyparis and Cryptomeria (Otto et al., perus virginiana L., Cupressaceae, and use thereof for treat The Botanical Review, April-June, 2001). ing and/or preventing infectious and immune diseases, in 0016 Hexane extracts from bark of Juniperus brevifolia particular that caused by HIV, as well as neoplasic patholo have been disclosed to include abietane-type diterpenoids g1eS. with alcohol function, fatty acids and sterols (Seca et al., Nat 0006 Ethanolic and aqueous extracts derived from berries Prod Res. 2008: 22(11):975-83).
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