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(12) Patent Application Publication (10) Pub. No.: US 2009/0136566A1 Krasutsky Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2009/0136566A1 Krasutsky Et Al US 20090 136566A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2009/0136566A1 Krasutsky et al. (43) Pub. Date: May 28, 2009 (54) THERAPEUTIC TRITERPENOIDS (60) Provisional application No. 60/792,097, filed on Apr. 13, 2006. (75) Inventors: Pavel A. Krasutsky, Duluth, MN (US); Igor V. Kolomitsyn, Duluth, MN (US); Jon M. Holy, Duluth, Publication Classification MN (US); Edward Leon Perkins, (51) Int. Cl. Duluth, MN (US): Oksana A 6LX 9/27 (2006.01) Kolomitsyna, Duluth, MN (US) A6II 3/565 (2006.01) A6IR 8/63 (2006.01) Correspondence Address: C07J 75/00 (2006.01) SCHWEGMAN, LUNDBERG & WOESSNER, P.A. A6IP35/00 (2006.01) P.O. BOX 2938 (52) U.S. Cl. ........... 424/450; 514/170: 514/171; 424/59; MINNEAPOLIS, MN 55402 (US) 552/514 (73) Assignee: Regents of the University of Minnesota, St. Paul, MN (US) (57) ABSTRACT (21) Appl. No.: 12/250,401 The present invention relates generally to compositions that can be obtained by extraction of birch bark, methods of using (22) Filed: Oct. 13, 2008 Such compositions (e.g., methods of medical use, cosmetic use and/or pharmaceutical use), food products and methods Related U.S. Application Data of manufacturing Such compounds. The compositions are (63) Continuation of application No. PCT/US2007/ triterpenes, triterpene alcohols, or derivatives of triterpene 066632, filed on Apr. 13, 2007. alcohols. 100 90 80 6 70 S 60 5 SO 5 40 & 30 20 10-: X XX xx X- X XX kx xx 1 2 3 4. 5 6 7 8 9 1O 11 12 13 14 15 16 17 18 SAMPLENO. Patent Application Publication May 28, 2009 Sheet 1 of 6 US 2009/O13656.6 A1 1 O 14 15 16 17 18 SAMPLENO. FIG 1 Patent Application Publication May 28, 2009 Sheet 2 of 6 US 2009/O13656.6 A1 FIG 2 Patent Application Publication May 28, 2009 Sheet 3 of 6 US 2009/O13656.6 A1 100 8 6 TO\IN00% 4 20 Ø|~ Ø], CELL LINE FIG, 3A 100 TOHINOO% Z CELL LINE FIG 3B Patent Application Publication May 28, 2009 Sheet 4 of 6 US 2009/O13656.6 A1 18O 160 140 120 100 80 60 40 Z 7 Z W2 KEN PAP NEO BetA Bet3 C FIG, 4 Patent Application Publication May 28, 2009 Sheet 5 of 6 US 2009/O13656.6 A1 O OH 10018 13341 15.375 FIG 5B 2.5 1.5 -O- UW SPECTRUM 0.5 O SRS SRS & RS RS S-S-S-S S. KSSS S-S-S-S-S-S-S-S-S- nm FIG 5C Patent Application Publication May 28, 2009 Sheet 6 of 6 US 2009/O13656.6 A1 -0-BETULAPAPYRIFERA, -- BETULAVERRUCOSA C= 0.23mgmL C=O29mgml 200 210 220 230 240 250 260 270 280 290 300 310 320 330 340 350 WAVELENGTH,m FIG. 6 US 2009/O 13656.6 A1 May 28, 2009 THERAPEUTIC TRITERPENOIDS these compositions as antibiotics. Some of the compositions of the invention can be obtained by the extraction of birch RELATED APPLICATIONS bark. Other inventive compositions can be derived from the chemical derivatization of natural product birch bark con 0001. This application is a continuation under 35 U.S.C. stituents and their structural analogs. Methods of semi-syn 111 (a) of International Application No. PCT/US2007/ 066632, filed Apr. 13, 2007 and published as WO 2007/ thesis of these compounds are also provided. 121352 on Oct. 25, 2007, which claims priority from U.S. 0007. The present invention is directed to a composition Provisional Application No. 60/792,097, filed Apr. 13, 2006, that includes at least two of: (a) betulin 3-caffeate; (b) betu which applications are incorporated herein by reference in linic acid; (c) oleanolic acid; (d) betulin; (e) lupeol, (f) 3-ac their entirety. etoxyoleanolic acid; (g) betulin aldehyde: (h) betulonic alde hyde; and (i) pycarehic acid (betulinic acid-3-caffeate); FIELD OF THE INVENTION wherein the composition is essentially free of plant tissue. 0008. The present invention also is directed to a composi 0002 The field of the present invention is the use of certain triterpene derivatives including esters, which can be extracted tion that includes: (a) betulin3-caffeate; (b) betulinic acid; (c) from birch bark or prepared by derivatization of birch bark oleanolic acid; (d) betulin; (e) lupeol, (f) 3-acetoxyoleanolic constituents, as dietary Supplements, cosmetic ingredients, acid; (g) betulin aldehyde: (h) betulonic aldehyde; and (i) antibiotics Such as anti-bacterials, anti-fungals, anti-protoZo pycarehic acid (betulinic acid 3-caffeate); wherein the com ans and anti-parasitics, and in the prevention and treatment of position is essentially free of plant tissue. CaCC. 0009. The present invention also is directed to a composi tion that includes: (a) up to about 10.0 wt.% of betulin BACKGROUND OF THE INVENTION 3-caffeate; (b) up to about 20.0 wt % of betulinic acid; (c) up to about 10.0 wt.% of oleanolic acid; (d) up to about 80.0 wt. 0003 Birch bark is at the present time a low value product % of betulin; (e) up to about 15.0 wt.% of lupeol, (f) up to in the forest products industry. Eckman, R. (1983), Holzfor about 15.0 wt.% of 3-acetoxyoleanolic acid; (g) up to about Schung, 37, 205. A single paper mill can generate 70 tons of 1.5 wt.% of betulin aldehyde: (h) up to about 1.0 wt.% of birch bark per day. Birch bark is a potential source for a betulonic aldehyde; and (i) up to about 10.0 of pycarehic acid variety of organic chemicals; several triterpenoids have been identified in birch bark extracts. For example lupeol, betulin, (betulinic acid 3-caffeate); wherein the composition is essen betulin aldehyde, betulinic acid, methyl betulinate, lupenone, tially free of plant tissue. In the inventive compositions, when betulonic aldehyde, betulonic acid, B-amyrin, erythrodiol, present in the composition, the disclosed compounds are oleanolic aldehyde, oleanolic acid, methyl oleanolate, and present in any Suitable and effective amount. acetyl oleanolic acid are all present in the bark of Betula 0010. An embodiment of the invention also provides a verrucosa. Eckerman, C. (1985), Paperija Puu, 3, 100. method of treating a hyperproliferative disease in a mammal, 0004 Some of these components have been shown to have the method includes administering to the mammal in need of useful pharmacologic properties; for instance, the anti-viral such treatment an effective amount of any of the above activity of betulin, such as against herpesvirus, has been described compositions in a dosage, at a frequency, and for a demonstrated (U.S. Pat. No. 5,750,578). Betulin has also duration of time sufficient to provide a beneficial result. been shown to possess anti-inflammatory activity (Recio, M. 0011. An embodiment of the invention also provides a (1995), Planta Med., 61, 5). Betulinic acid has been shown to method of treating a hyperproliferative disease in a mammal, have antitumor activity against human melanoma, (Pisha, E., the method includes administering to the mammal in need of et al. (1995), J. M. Nature Medicine, 1, 1046) and anti-HIV Such treatment an effective amount of a compound of formula activity (Fujioka, T., et al. (1994), J. Nat. Prod., 57, 243). Lupeol caffeate has been shown to have anti-malarial activity (I) (Chumkaew, P., et al. (2005), Chem. Pharm. Bull. 53(1), 95-96. (I) 0005. There is an ongoing need for new and improved bioactive agents active against a wide variety of malcondi tions, such as viral infections, bacterial and fungal infections, cancer, and others. There is also a need for compositions useful for skin health (cosmetic ingredients) and for use as dietary Supplements to improve overall health. Lastly, there is a need to utilize the abundant natural resource of birch bark in productive ways. SUMMARY OF THE INVENTION 0006 Embodiments of the present invention concern compositions comprising triterpene derivatives, including esters, such as unsaturated aralkenoyl esters. Further embodi wherein the substituents are as defined herein. ments are directed to methods of using these compositions in 0012. The present invention also provides a method of the treatment of hyperproliferative diseases such as cancer, as treating a hyperproliferative disease in a mammal, the method dietary Supplements, and as cosmetic ingredients such as UV includes administering to the mammal in need of such treat screens. Other embodiments are directed to methods of using ment an effective amount of a compound of formula (II) US 2009/O 13656.6 A1 May 28, 2009 (II) (IVA) -N N-(N- "Je O (Z) wherein 0016 the non-aromatic carbon-carbon double bond is in the cis- or trans-configuration; 0017 n is 0-5; m is 0-5: 0018 p is 0-5, provided that m+p is less than or equal to a total of 5; 0019 each Y is independently alkyl, alkenyl, alkoxy, halo, haloalkyl, hydroxy, hydroxyalkyl, aryl, heteroaryl, hetero wherein the substituents are as defined herein. cycle, cycloalkyl, alkanoyl, acyloxy, alkoxycarbonyl, acy 0013 The present invention also provides a method of lamino, nitro, trifluoromethyl, trifluoromethoxy, carboxy, treating a hyperproliferative disease in a mammal, the method carboxyalkyl, alkylthio, alkylsulfinyl, alkylsulfonyl, cyano, includes administering to the mammal in need of such treat acetamido, acetoxy, acetyl, arylamido, arylsulfinyl, arylsul ment an effective amount of a compound of formula (III) fonamido, arylsulfonyl, arylsulfonylamino, aroyl, arylamino, aroyloxy, aralkyl, aralkyloxy, aralkyloxycarbonyl, aralky lthio, carbamoyl, carbamate, isocyanato, Sulfamoyl, Sulfi (III) namoyl, sulfino, sulfo, sulfoamino, thiosulfo, NR'R' or COOR, wherein each R and R' is independently at each occurrence H, or substituted or unsubstituted alkyl, alkenyl, aryl, heteroaryl, heterocyclyl, or cycloalkyl; each Z is inde pendently H, OH or hydroxyalkyl; and 0020 Q comprises a residue of betulin, betulinic acid, ursolic acid, oleanic acid, allobetulin, allobetulin lactone, lupeol, or a pentacyclic triterpene alcohol; bonded by a hydroxyl thereof to the carbonyl group.
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