(12) Patent Application Publication (10) Pub. No.: US 2015/0133552 A1 Hans Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2015/0133552 A1 Hans Et Al US 2015O133552A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2015/0133552 A1 Hans et al. (43) Pub. Date: May 14, 2015 (54) POLYHYDROXYLATED PENTACYCLC Publication Classification TRITERPENE ACIDSAS HMG-COA REDUCTASE INHIBITORS (51) Int. Cl. CD7C 62/32 (2006.01) (71) Applicants: Torsten Grothe, (US); Joachim HANS, A6II 45/06 (2006.01) (US) A63L/9I (2006.01) (52) U.S. Cl. (72) Inventors: Joachim Hans, Holzminden (DE); CPC ............... C07C 62/32 (2013.01); A61 K3I/191 Kathrin Reinhardt, Munster (DE); (2013.01); A61K 45/06 (2013.01) Torsten Grothe, Affoltern am Albis (CH); Ingo Wöhrle, Dortmund (DE): (57) ABSTRACT Jana Moldenhauer, Dortmund (DE); The present invention relates to certain polyhydroxylated Barbel Köpcke, Dortmund (DE); pentacyclic triterpene acids of formula (I) for use as HMG Thomas Kiper, Reken (DE); Jens CoA reductase inhibitors in the prophylactic and/or therapeu Bitzer, Dortmund (DE) tic treatment of a disease, disorder or condition that responds to a reduction of the HMG-CoA reductase activity in a mam (73) Assignee: Joachim HANS, Holzminden (DE) mal, preferably a human being. The present invention further (21) Appl. No.: 14/401,699 relates to certain mixtures and plant extracts comprising eus caphic acid and tormentic acid, wherein the amount of eus (22) PCT Fled: May 7, 2013 caphic acid to tormentic acid exceeds a certain ratio. Further, the present invention also relates to a formulation, preferably (86) PCT NO.: PCT/EP2013/059513 pharmaceutical or nutraceutical formulation, comprising one or more of said compounds of formula (I), a composition S371 (c)(1), according to the present invention or a plant extract according (2) Date: Nov. 17, 2014 to the present invention. Also, the present invention relates to a process for obtaining certain polyhydroxylated pentacyclic Related U.S. Application Data triterpene acids of formula (I), a composition according to the (60) Provisional application No. 61/647,617, filed on May present invention or a plant extract according to the present 16, 2012. invention. US 2015/O 133552 A1 May 14, 2015 POLYHYDROXYLATED PENTACYCLC 0006 For example, grape seed proanthocyanidin extract is TRITERPENE ACIDSAS HMG-COA reportedly cholesterol-lowering nutraceutical. The hypocho REDUCTASE INHIBITORS lesterolemic activity of grape seed proanthocyanidin is prob ably mediated by enhancement of bile acid excretion and CROSS-REFERENCES TO RELATED up-regulation of CYP7A1. APPLICATIONS 0007 HMG-CoA reductase (3-Hydroxy-3-Methyl-Glu taryl-CoA reductase; enzyme commission designation EC 0001. This application is a National Stage filing of Inter 1.1.1.88) is the rate-controlling enzyme of the mevalonate national Application PCT/EP 2013/059513, filed May 7, pathway, the metabolic pathway that produces cholesterol in 2013, entitled “POLYHYDROXYLATED PENTACYCLIC mammals. Normally, in mammalian cells this enzyme is Sup TRITERPENE ACIDS AS HMG-COA REDUCTASE pressed by cholesterol derived from the internalization and INHIBITORS. The subject application claims priority to degradation of low density lipoprotein (LDL, the “bad” cho PCT/EP 2013/059513, and U.S. Provisional Application lesterol) via the LDL receptor as well as oxidized species of 61/647,617 filed May 16, 2012, incorporates all by reference cholesterol. Competitive inhibitors of the reductase induce herein, in their entirety. the expression of LDL receptors in the liver, which in turn increases the catabolism of plasma LDL and lowers the BACKGROUND OF THE INVENTION plasma concentration of cholesterol, an important determi 0002 The present invention relates to certain polyhy nant of atherosclerosis. HMG-CoA reductase is anchored in droxylated pentacyclic triterpene acids of formula (I), par the membrane of the endoplasmic reticulum. ticularly of formula (I-A), defined hereinafter for use as 0008 HMG-CoA reductase is a polytopic, transmem HMG-CoA reductase inhibitors in the prophylactic and/or brane protein that catalyzes a key step in the mevalonate therapeutic treatment of a disease, disorder or condition that pathway, which is interalia involved in the synthesis of ste responds to a reduction of the HMG-CoA reductase activity rols. In mammals, in particular in human beings, the step in a mammal, preferably a human being. The present inven involving HMG-CoA reductase in the metabolic pathway of tion further relates to certain mixtures and plant extracts the cholesterol synthesis is rate-limiting and therefore repre comprising euscaphic acid and tormentic acid, wherein the sents a major drug target for contemporary cholesterol-low amount of euScaphic acid to tormentic acid exceeds a certain ering drugs. The medical significance of HMG-CoA reduc ratio. Further, the present invention also relates to a formula tase has continued to expand beyond its direct role in tion, preferably pharmaceutical or nutraceutical formulation, cholesterol synthesis following the discovery that it can offer comprising one or more of said compounds of formula (I), a cardiovascular health benefits independent of cholesterol composition according to the present invention or a plant reduction. extract according to the present invention. Also, the present 0009 Statins are used to lower serum cholesterol levels as invention relates to a process for obtaining certain polyhy a means of reducing the risk for cardiovascular disease by droxylated pentacyclic triterpene acids of formula (I), a com potently inhibiting the enzyme HMG-CoA reductase, which position according to the present invention or a plant extract plays a central role in the production of cholesterol in the according to the present invention. liver. Increased cholesterol levels have been associated with 0003 Cholesterol is mainly an issue because blood total cardiovascular diseases, and statins are therefore used in the cholesterol and low density lipoprotein correlate strongly prevention of these diseases. Statins are very effective for with coronary heart disease. Cholesterol homeostasis is treating cardiovascular disease, with questionable benefit in maintained by a complex mechanism of sterol absorption, those without previous cardiovascular disease but with anabolism, catabolism and excretion. elevated cholesterol levels. Statins are currently the most 0004 Hypocholesteremic agents, i.e. agents that lower the widely used drugs for prevention and treatment of atheroscle (plasma) cholesterol level by influencing the cholesterol rosis. However, statins are reported to have adverse side metabolism, are considered to be beneficial for the health of effects such as hepatotoxicity, muscle pain, kidney damage mammals, in particular human beings. For example, by and weakness. avoiding an increase in arterial cholesterol and preferably by 0010 Statins include for example rosuvastatin, lovastatin, lowering the plasma cholesterol level, the formation of pre atorvastatin, pravastatin, fluvastatin and simvastatin. Several cursors of fatty streak, an early lesion in the atherosclerotic cholesterol-lowering statins are naturally occurring. Red process, may beneficially be influenced. Cholesterol metabo yeast rice contains statins known as monacolins, including lism is complex and hitherto several different approaches mevastatin and the highly active lovastatin; the latter can also using different pathways have been proposed to positively be found in oyster mushrooms. influence the (plasma) cholesterol level in mammals and 0011. Acyl-CoA: cholesterol acyltransferase ACAT; also avoid or reduce hypercholesterolemia, foam cells, fatty referred to as sterol O-acyltransferase (SOAT); enzyme com streak, atherosclerotic lesion, atheroma and ultimately ath mission designation EC 2.3.1.26 catalyzes the acylation of erosclerosis. cholesterol to cholesteryl ester with long chain fatty acids and 0005 Generally speaking, cholesterol-lowering func ACAT inhibition is also an useful strategy for treating hyper tional foods and nutraceuticals may be classified into several cholesterolemia or atherosclerosis. It has rather recently been different types, mainly based on their respective mechanistic revealed that ACAT exists in the form of two isozymes, activity. These mechanistic types include intestinal acyl namely ACAT 1 (expressed in many cells and tissues) and CoA:cholesterol acyltransferase (ACAT) inhibitors, 3-hy ACAT 2 (expressed specifically in the small intestine and droxy-3-methylglutaryl (HMG-CoA) reductase inhibitors, liver), which have different in vivo functions from each other. LDL receptor up-regulators, bile acid reabsorption inhibitors, For example, ursolic acid, oleanolic acid, and betulinic acid, and cholesterol-7C-hydroxylase (CYP7A1) activators. e.g. obtainable from the methanol extracts of the leaves of US 2015/O 133552 A1 May 14, 2015 Lycopus lucidus, are ACAT-inhibitors. Betulinic acid has 0023 Surprisingly, it has now been found that a certain been described in the literature as potent inhibitor of human group of compounds, namely the polyhydroxylated pentacy ACAT 1 and human ACAT 2. clic triterpene acids of formula (I) as defined herein and the 0012. Other drugs, like eZetimibe, lower the cholesterol physiologically acceptable salts thereof, have the property to level by decreasing cholesterol absorption in the intestine. inhibit (i.e. reduce the activity of) mammalian HMG-CoA These may be used alone or together in combination with reductase, in particular human HMG-CoA reductase. They statins (e.g., eZetimibe and simvastatin). are thus useful in the (prophylactic and/or therapeutic)
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