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WO 2013/171100 Al 21 November 2013 (21.11.2013) P O P C T

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WO 2013/171100 Al 21 November 2013 (21.11.2013) P O P C T (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date WO 2013/171100 Al 21 November 2013 (21.11.2013) P O P C T (51) International Patent Classification: (74) Agent: STREHLKE, Ingo, K.; VON ROHR PAT- A61K 31/56 (2006.01) A61K 36/73 (2006.01) ENTANWALTE PARTNERSCHAFT, Ruttenscheider Strasse 62, 45130 Essen (DE). (21) International Application Number: PCT/EP2013/0595 13 (81) Designated States (unless otherwise indicated, for every kind of national protection available): AE, AG, AL, AM, (22) International Filing Date: AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, 7 May 2013 (07.05.2013) BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, (25) Filing Language: English DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, (26) Publication Language: English KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, (30) Priority Data: ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, 61/647,617 16 May 2012 (16.05.2012) US NO, NZ, OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, (72) Inventors; and TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, (71) Applicants : HANS, Joachim [DE/DE]; Olgastrasse 5, ZM, ZW. 4414 1 Dortmund (DE). GROTHE, Torsten [DE/DE]; Hernerstrasse 212, 44809 Bochum (DE). (84) Designated States (unless otherwise indicated, for every kind of regional protection available): ARIPO (BW, GH, (72) Inventors; and GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, SZ, TZ, (71) Applicants (for US only): WOHRLE, Ingo [DE/DE]; UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, TJ, Ortli 9, 44265 Dortmund (DE). MOLDENHAUER, Jana TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, [DE/DE]; Feldbank 72, 44265 Dortmund (DE). KOP- EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, ΓΓ, LT, LU, LV, CKE, Barbel [DE/DE]; Baroper Schulstrasse 1A, 44225 MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, Dortmund (DE). KUPER, Thomas [DE/DE]; Stephan- TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, strasse 28, 48734 Reken (DE). BITZER, Jens [DE/DE]; ML, MR, NE, SN, TD, TG). Wildrosenstrasse 30, 44225 Dortmund (DE). REIN- HARDT, Kathrin [DE/DE]; Am Beisenufer 12, 44225 Dortmund (DE). [Continued on nextpage] (54) Title: POLYHYDROXYLATED PENTACYCLIC TRITERPENE ACIDS AS HMG-COA REDUCTASE INHIBITORS (57) Abstract: The present invention relates to certain polyhydroxylated pentacyclic triterpene acids of formula (I) for use as HMG-Co A re ductase inhibitors in the prophylactic and/or therapeutic treatment of a disease, disorder or condition that responds to a reduction of the HMG-Co A reductase activity in a mammal, preferably a human being. The present invention further relates to certain mixtures and plant ex tracts comprising euscaphic acid and tormentic acid, wherein the amount of euscaphic acid to tormentic acid exceeds a certain ratio. Further, the present invention also relates to a formula tion, preferably pharmaceutical or nutraceutical formulation, comprising one or more of said compounds of formula (I), a composition ac cording to the present invention or a plant ex tract according to the present invention. Also, the present invention relates to a process for ob o taining certain polyhydroxylated pentacyclic o triterpene acids of formula (I), a composition ac cording to the present invention or a plant ex (I) tract according to the present invention. w o 2013/171100 A i llll II II 11III III 1 1 III II I II II III II I II Declarations under Rule 4.17: before the expiration of the time limit for amending the — as to the applicant's entitlement to claim the priority of claims and to be republished in the event of receipt of the earlier application (Rule 4.17(Hi)) amendments (Rule 48.2(h)) Published: Polyhydroxylated pentacyclic triterpene acids as HMG-CoA reductase inhibitors The present invention relates to certain polyhydroxylated pentacyclic triterpene acids of formula (I), particularly of formula (l-A), defined hereinafter for use as HMG-CoA reductase inhibitors in the prophylactic and/or therapeutic treatment of a disease, disorder or condition that responds to a reduction of the HMG-CoA reductase activity in a mammal, preferably a human being. The present invention further relates to certain mixtures and plant extracts comprising euscaphic acid and tormentic acid, wherein the amount of euscaphic acid to tormentic acid exceeds a certain ratio. Further, the present invention also relates to a formulation, preferably pharmaceutical or nutraceutical formulation, comprising one or more of said compounds of formula (I), a composition according to the present invention or a plant extract according to the present invention. Also, the present invention relates to a process for obtaining certain polyhydroxylated pentacyclic triterpene acids of formula (I), a composition according to the present invention or a plant extract according to the present invention. Cholesterol is mainly an issue because blood total cholesterol and low density lipoprotein correlate strongly with coronary heart disease. Cholesterol homeostasis is maintained by a complex mechanism of sterol absorption, anabolism, catabolism and excretion. Hypocholesteremic agents, i.e. agents that lower the (plasma) cholesterol level by influencing the cholesterol metabolism, are considered to be beneficial for the health of mammals, in particular human beings. For example, by avoiding an increase in arterial cholesterol and preferably by lowering the plasma cholesterol level, the formation of precursors of fatty streak, an early lesion in the atherosclerotic process, may beneficially be influenced. Cholesterol metabolism is complex and hitherto several different approaches using different pathways have been proposed to positively influence the (plasma) cholesterol level in mammals and avoid or reduce hypercholesterolemia, foam cells, fatty streak, atherosclerotic lesion, atheroma and ultimately atherosclerosis. Generally speaking, cholesterol-lowering functional foods and nutraceuticals may be classified into several different types, mainly based on their respective mechanistic activity. These mechanistic types include intestinal acyl-CoA:cholesterol acyltransferase (ACAT) inhibitors, 3-hydroxy-3-methylglutaryl (HMG-CoA) reductase inhibitors, LDL receptor up- regulators, bile acid reabsorption inhibitors, and cholesterol-7a-hydroxylase (CYP7A1 ) activators. For example, grape seed proanthocyanidin extract is reportedly cholesterol-lowering nutraceutical. The hypocholesterolemic activity of grape seed proanthocyanidin is probably mediated by enhancement of bile acid excretion and up-regulation of CYP7A1 . HMG-CoA reductase (3-Hydroxy-3-Methyl-Glutaryl-CoA reductase; enzyme commission designation EC 1. 1 . 1 .88) is the rate-controlling enzyme of the mevalonate pathway, the metabolic pathway that produces cholesterol in mammals. Normally, in mammalian cells this enzyme is suppressed by cholesterol derived from the internalization and degradation of low density lipoprotein (LDL, the "bad" cholesterol) via the LDL receptor as well as oxidized species of cholesterol. Competitive inhibitors of the reductase induce the expression of LDL receptors in the liver, which in turn increases the catabolism of plasma LDL and lowers the plasma concentration of cholesterol, an important determinant of atherosclerosis. HMG-CoA reductase is anchored in the membrane of the endoplasmic reticulum. HMG-CoA reductase is a polytopic, transmembrane protein that catalyzes a key step in the mevalonate pathway, which is inter alia involved in the synthesis of sterols. In mammals, in particular in human beings, the step involving HMG-CoA reductase in the metabolic pathway of the cholesterol synthesis is rate-limiting and therefore represents a major drug target for contemporary cholesterol-lowering drugs. The medical significance of HMG-CoA reductase has continued to expand beyond its direct role in cholesterol synthesis following the discovery that it can offer cardiovascular health benefits independent of cholesterol reduction. Statins are used to lower serum cholesterol levels as a means of reducing the risk for cardiovascular disease by potently inhibiting the enzyme HMG-CoA reductase, which plays a central role in the production of cholesterol in the liver. Increased cholesterol levels have been associated with cardiovascular diseases, and statins are therefore used in the prevention of these diseases. Statins are very effective for treating cardiovascular disease, with questionable benefit in those without previous cardiovascular disease but with elevated cholesterol levels. Statins are currently the most widely used drugs for prevention and treatment of atherosclerosis. However, statins are reported to have adverse side effects such as hepatotoxicity, muscle pain, kidney damage and weakness. Statins include for example rosuvastatin, lovastatin, atorvastatin, pravastatin, fluvastatin and simvastatin. Several cholesterol-lowering statins are naturally occurring. Red yeast rice contains statins known as monacolins, including mevastatin and the highly active lovastatin; the latter can also be found in oyster mushrooms. Acyl-CoA: cholesterol acyltransferase [ACAT; also referred to as sterol O-acyltransferase (SOAT); enzyme commission designation EC 2.3.1 .26] catalyzes the acylation of cholesterol to cholesteryl ester with long chain fatty acids and ACAT inhibition is also an useful
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