Novel 3-hydroxy-3-methylglutaryl-coenzyme A reductase inhibitors: a patent review

Bibliography

• Gaziano JM. Global burden of cardiovascular disease. In: Braunwald E, Zipes DP, Libby P, editors, Heart disease. 6th edition. W.B. Saunders Co., Philadelphia; 2001. p. 1-18
   Google Scholar
• American Heart Association. Heart disease and stroke statistics – 2010 update. 2010. Available from: http://circ.ahajournals.org/cgi/reprint/CIRCULATIONAHA.109.192667
   Google Scholar
• Verschuren WM, Jacobs DR, Bloemberg BP, Serum total cholesterol and long-term coronary heart disease mortality in different cultures. Twenty-five-year follow-up of the seven countries study. JAMA 1995;274:131-6
   PubMed Web of Science ®Google Scholar
• Manninen V, Tenkanen L, Koskinen P, Joint effects of serum triglyceride and LDL cholesterol and HDL cholesterol concentrations on coronary heart disease risk in the Helsinki Heart Study; Implication for treatment. Circulation 1992;85:37-45
   PubMed Web of Science ®Google Scholar
• Wilson PW, Kannel WB, Silbershatz H, Clustering of metabolic factors and coronary heart disease. Arch Intern Med 1999;159:1104-9
   PubMed Web of Science ®Google Scholar
• Kastelein JJP. The future of best practice. Atherosclerosis 1999;143:S17-21
   PubMedGoogle Scholar
• McKenney JM. Pharmacologic characteristics of statins. Clin Cardiol 2003;26(Suppl III):32-8
   Google Scholar
• Tobert JA. Lovastatin and beyond: the history of the HMG-CoA reductase inhibitors. Nat Rev Drug Discov 2003;2:517-26
   PubMed Web of Science ®Google Scholar
• LaRosa JC, He J, Vupputuri S. Effects of statins on risk of coronary disease. JAMA 1999;282:2340-6
   PubMed Web of Science ®Google Scholar
• Armitage J. The safety of statins in clinical practice. Lancet 2007;370:1781-90
   PubMed Web of Science ®Google Scholar
• Zhou Q, Liao JK. Pleotropic effects of statins. Circ J 2010;74:818-26
   PubMed Web of Science ®Google Scholar
• Zhou Q, Liao JK. Statins and cardiovascular disease: from cholesterol lowering to pleiotropy. Curr Pharm Des 2009;15:467-78
   PubMed Web of Science ®Google Scholar
• Athyros VG, Kakafika AI, Tziomalos K, Pleotropic effects of statins – clinical evidence. Curr Pharm Des 2009;15:479-89
   PubMed Web of Science ®Google Scholar
• Steinberg D, Glass CK, Witztum JL. Evidence mandating earlier and more aggressive treatment of hypercholesterolemia. Circulation 2008;118:672-7
   PubMed Web of Science ®Google Scholar
• LaRosa JC, Grundy SM, Walters DD, Intensive lipid lowering with atorvastatin in patients with stable coronary disease. N Engl J Med 2005;352:1425-35
   PubMed Web of Science ®Google Scholar
• Schwartz G, Olsson AG, Ezekowitz MD, Effects of atorvastatin on early recurrent ischemic events in acute coronary syndromes: the MIRACL study: a randomized controlled trial. JAMA 2001;285:1711-18
   PubMed Web of Science ®Google Scholar
• Cannon CP, Braunwald E, McCabe CH, Intensive versus moderate lipid lowering with statins after acute coronary syndromes. N Engl J Med 2004;350:1495-504
   PubMed Web of Science ®Google Scholar
• Cannon CP, Steinberg BA, Murphy SA, Meta-analysis of cardiovascular outcome trials comparing intensive versus moderate statin therapy. J Am Coll Cardiol 2006;48:438-45
   PubMed Web of Science ®Google Scholar
• Grundy SM, Cleeman JI, Merz NB, Implications of recent clinical trials for the National Cholesterol Education Adult Treatment Panel III guidelines. Circulation 2004;110:227-39
   PubMed Web of Science ®Google Scholar
• Keefe JH, Cordain L, Harris WH, Optimal low-density lipoprotein is 50 to 70 mg/dl. J Am Coll Cardiol 2004;43:2142-6
   PubMedGoogle Scholar
• Wiviott SD, Cannon CP, Morrow DA, Can low-density lipoprotein be too low? The safety and efficacy of achieving very low-density lipoprotein with intensive statin therapy: a PROVE-IT-TIMI 22 sub-study. J Am Coll Cardiol 2005;46:1411-16
   PubMed Web of Science ®Google Scholar
• Leeper NJ, Ardehali R, deGoma EM, Statin use in patients with extremely low low-density lipoprotein levels is associated with improved survival. Circulation 2007;116:613-18
   PubMed Web of Science ®Google Scholar
• Patel TN, Shishehbor MH, Bhatt DL. A review of high dose statin therapy: targeting cholesterol and inflammation in atherosclerosis. Eur Heart J 2007;28:664-72
   PubMed Web of Science ®Google Scholar
• McKenney JM, Jones PH, Bays HE, Comparative effects on lipid levels of combination therapy with a statin and extended release niacin or ezetimibe versus a statin alone (the COMPELL study). Atherosclerosis 2007;192:432-7
   PubMed Web of Science ®Google Scholar
• Ridker PM, Danielson E, Fonseca FA, ; The JUPITOR Study Group. Rosuvastatin to prevent vascular events in men and women with elevated C-reactive protein. N Engl J Med 2008;359:2195-207
   PubMed Web of Science ®Google Scholar
• Ridker PM. moving toward new statin guidelines in a post-JUPITOR world: principles to consider. Curr Atherosclerosis Rep 2009;11:249-56
   PubMedGoogle Scholar
• Bates TR, Connaughton VM, Watts GF. Non-adherence to statin therapy: a major challenge for preventive cardiology. Expert Opin Pharmacother 2009;10:2973-85
   PubMed Web of Science ®Google Scholar
• Franc S, Dejager S, Bruckert E, A comprehensive description of muscle symptoms associated with lipid-lowering drugs. Cardiovasc Drugs Ther 2003;17:459-65
   PubMed Web of Science ®Google Scholar
• Baer AN, Wortmann RL. Myotoxicity associated with lipid-lowering drugs. Curr Opin Rheumatol 2007;19:67-73
   PubMed Web of Science ®Google Scholar
• Tiwari A, Bansal V, Chugh A, Statins and myotoxicity: a therapeutic limitation. Expert Opin Drug Saf 2006;5:651-66
   PubMed Web of Science ®Google Scholar
• Omar MA, Wilson JP, Cox TS. Rhabdomyolysis and HMG-CoA reductase inhibitors. Ann Pharmacother 2001;35:1096-107
   PubMed Web of Science ®Google Scholar
• Brukert E, Hayem G, Dejager S, Mild to moderate muscular symptoms with high-dosage statin therapy in hyperlipidemic patients–The PRIMO study. Cardiovasc Drugs Ther 2005;19:403-14
   PubMedGoogle Scholar
• Athar H, Shah AR, Thompson PD. Possible mechanisms for statin myopathy and its relationship to physical exercise. Future Lipidol 2006;1:143-51
   Web of Science ®Google Scholar
• Hamelin BA, Turgeon J. Hydrophilicity/lipophilicity: relevance for the pharmacology and clinical effects of HMG-CoA reductase inhibitors. Trends Pharm Sci 1998;19:26-37
   PubMed Web of Science ®Google Scholar
• Pfefferkorn JA. Muscle sparing statins: preclinical profiles and future clinical use. Curr Opin Invest Drugs 2009;10:245-52
   PubMedGoogle Scholar
• Bristol-Myers Squibb Co. HMG-CoA reductase inhibitors and method. US20020094977; 2002
   Google Scholar
• Bristol-Myers Squibb Co. HMG-CoA reductase inhibitors and method. WO2005051386; 2005
   Google Scholar
• Bristol-Myers Squibb Co. Pyrimidine and pyridine derivatives useful as HMG-CoA reductase inhibitors and methods for the preparation thereof. WO2005030758; 2005
   Google Scholar
• Ahmad S, Madsen CS, Stein PD, (3R,5S,E)-7-(4-(4-Fluorophenyl)-6-isopropyl-2-(methyl(1-methyl-1H-1,2,4-triazol-5-yl)amino)pyrimidin-5-yl)-3,5-dihydroxyhept-6-enoic acid (BMS-644950): a rationally designed orally efficacious 3-hydroxy-3-methylglutaryl coenzyme-A reductase inhibitor with reduced myotoxicity potential. J Med Chem 2008;51:2722-33
   PubMedGoogle Scholar
• Madsen CS, Janovitz E, Cuff CC, The guinea pig as a preclinical model for demonstrating the efficacy and safety of statins. J Pharmacol Exp Ther 2008;324:576-86
   PubMed Web of Science ®Google Scholar
• Martin PD, Mitchell PD, Schneck DW. Pharmacodynamic effects and pharmacokinetics of a new HMG-CoA reductase inhibitor, rosuvastatin, after morning or evening administration in healthy volunteers. Br J Clin Pharmacol 2002;54:472-7
   PubMed Web of Science ®Google Scholar
• Pfizer (Warner-Lambert Co.). Novel imidazoles. US20050239857; 2005
   Google Scholar
• Pfefferkorn JA, Litchfield J, Hutchings R, Discovery of novel hepatoselective HMG-CoA reductase inhibitors for treating hypercholesterolemia: a bench-to-bedside case study on tissue selective drug distribution. Bioorg Med Chem Lett 2010; In press
   Google Scholar
• Pfizer (Warner-Lambert Co.). Imidazole-based HMG-CoA reductase inhibitors. WO2005079790; 2005
   Google Scholar
• Pfizer (Warner-Lambert Co.). Novel pyrazole-based HMG CoA reductase inhibitors. US20060111422; 2006
   Google Scholar
• Pfefferkorn JA, Choi C, Larsen SD, Substituted pyrazoles as hepatoselective HMG-CoA reductase inhibitors: discovery of (3R,5R)-7-[2-(4-fluoro-phenyl)-4-isopropyl-5-(4-methyl-benzylcarbamoyl)-2H-pyrazol-3-yl]-3,5-dihydroxyheptanoic acid (PF-3052334) as a candidate for the treatment of hypercholesterolemia. J Med Chem 2008;51:31-45
   PubMedGoogle Scholar
• Pfefferkorn JA, Choi C, Larsen SD, Pyrazoles as hepatoselective HMG-CoA reductase inhibitors: discovery and early clinical evaluation of PF-3052334 for the treatment of hypercholesterolemia. 31st National Medicinal Chemistry Symposium, 15 – 19 June 2008; Pittsburgh, PA; 2008. p. NMCS-124
   Google Scholar
• Pfizer (Warner-Lambert Co.). Oxypyrazoles HMG-CoA reductase inhibitors. WO2006087630; 2006
   Google Scholar
• Larsen SD, Poel T-J, Filipski KJ, Pyrazole inhibitors of HMG-CoA reductase: an attempt to dramatically reduce synthetic complexity through minimal analog redesign. Bioorg Med Chem Lett 2007;17:5567-72
   PubMedGoogle Scholar
• Pfizer (Warner-Lambert Co.). N-Alkyl pyrroles as HMG-CoA reductase inhibitors. WO2005056004; 2005
   Google Scholar
• Pfefferkorn JA, Song Y, Sun KL, Design and synthesis of hepatoselective, pyrrole-based HMG-CoA reductase inhibitors. Bioorg Med Chem Lett 2007;17:4538-44
   PubMedGoogle Scholar
• Bratton L, Auerbach B, Choi C, Discovery of pyrrole-based hepatoselective ligands as potent inhibitors of HMG-CoA reductase. Bioorg Med Chem 2007;15:5576-89
   PubMedGoogle Scholar
• Pfefferkorn JA, Bowles DM, Kissel W, Development of a practical synthesis of novel, pyrrole-based HMG-CoA reductase inhibitors. Tetrahedron 2007;63:8124-34
   Google Scholar
• Pfizer (Warner-Lambert Co.). Fused bicyclic pyrroles as HMG-CoA reductase inhibitors. WO2006059210; 2006
   Google Scholar
• Pfefferkorn JA, Choi C, Song Y, Design and synthesis of novel, conformationally restricted HMG-CoA reductase inhibitors. Bioorg Med Chem Lett 2007;17:4531-7
   PubMedGoogle Scholar
• Pfizer (Warner-Lambert Co.). Novel pyrrole-based HMG-CoA reductase inhibitors. US20050043364; 2005
   Google Scholar
• Park WKC, Kennedy RM, Larsen SD, Hepatoselectivity of statins: design and synthesis of 4-sulfamoyl pyrroles as HMG-CoA reductase inhibitors. Bioorg Med Chem Lett 2008;18:1151-6
   PubMedGoogle Scholar
• Ranbaxy Pharmaceuticals. Substituted pyrrole derivatives. US20040102511; 2004
   Google Scholar
• Ranbaxy Pharmaceuticals. Substituted pyrrole derivatives as HMG-CoA reductase inhibitors and their preparation, pharmaceutical compositions and use in the treatment of cholesterol-related diseases. US20070149605; 2007
   Google Scholar
• Ranbaxy Pharmaceuticals. Substituted pyrrole derivatives as HMG-CoA reductase inhibitors. WO2004105752; 2004
   Google Scholar
• Ranbaxy Pharmaceuticals. Substituted pyrrole derivatives and their use as HMG-CoA inhibitors. US20100056602; 2010
   Google Scholar
• Shanghai Institute of Pharmaceutical Industry. Quinoline compounds, pharmaceutical compositions, Preparation methods and uses thereof. WO2009132593; 2009
   Google Scholar
• Cai Z, Zhou W, Sun L. Synthesis and HMG CoA reductase inhibition of 4-thiophenyl quinolines as potential hypocholesterolemic agents. Bioorg Med Chem 2007;15:7809-29
   PubMed Web of Science ®Google Scholar
• Zhao S, Zhou W, Liu J. Synthesis and HMG-CoA reductase inhibition of 2-cyclopropyl-4-thiophenyl quinoline mevalonalactones. Bioorg Med Chem 2009;17:7915-23
   PubMedGoogle Scholar
• Wang S, Yao H. Preparation of pyrimidine derivatives as HMG-CoA reductase inhibitors. CN200410069193; 2004
   Google Scholar
• Wang S. Preparation of 2-pyridinone derivatives as HMG-CoA reductase inhibitors. CN200410102714; 2004
   Google Scholar
• Yao H. Preparation of pyrimidinone derivatives as HMG-CoA reductase inhibitors. WO2006066512; 2006
   Google Scholar
• Hosoda S, Matsuda D, Tomoda H, Application of a 3,3-diphenylpentane skeleton as a multi-template for creation of HMG-CoA reductase inhibitors. Bioorg Med Chem Lett 2009;19:4228-31
   PubMedGoogle Scholar
• Beri A, Sural N, Mahajan SB. Non-atheroprotective effects of statins. Am J Cardiovasc Drugs 2009;9:361-70
   PubMedGoogle Scholar
• Campbell CY, Rivera JJ, Blumenthal RS. Residual risk in statin-treated patients: future therapeutic options. Curr Cardiol Rep 2007;9:499-505
   PubMedGoogle Scholar
• Ansell BJ, Fonarow GC, Maki KC, Reduced treatment success in lipid management among women with coronary heart disease or risk equivalents: results of a national survey. Am Heart J 2006;152:976-81
   PubMedGoogle Scholar
• Waters DD, Brotons C, Chiang CW, Lipid treatment assessment project 2. A multinational survey to evaluate the proportion of patients achieving low-density lipoprotein treatment goals. Circulation 2009;120:28-34
   PubMed Web of Science ®Google Scholar
• Franks P, Tancredi D, Winters P, Fiscella K. Cholesterol treatment with statins: who is left out and who makes it to goal? BMC Health Serv Res 2010;10:68. Available from: http://www.biomedcentral.com/content/pdf/1472-6963-10-68.pdf
   Google Scholar
• Cannon CP, Guigliano RP, Blazing MA, Rationale and design of IMPROVE-IT (IMProved Reduction of Outcomes: Vytorin Efficacy International Trial): comparison of ezetimibe/simvastatin versus simvastatin monotherapy on cardiovascular outcomes in patients with acute coronary syndromes. Am Heart J 2008;156:826-32
   PubMed Web of Science ®Google Scholar
• Paras C, Hussain MM, Rosenson RS. Emerging drugs for hyperlipidemia. Expert Opin Emerg Drugs 2010;15:433-51
   PubMed Web of Science ®Google Scholar
• Tavridou A, Manolopoulos VG. Novel molecules targeting dyslipidemia and atherosclerosis. Curr Med Chem 2008;15:792-802
   PubMed Web of Science ®Google Scholar
• Kastelein JJ, Akdim F, Stroes ES. Simvastatin with or without ezetimibe in familial hypercholesterolemia. N Engl J Med 2008;358:1432-43
   Google Scholar
• Taylor AJ, Villines TC, Stanek EJ, Extended-release niacin or ezetimibe and carotid intima-media thickness. N Engl J Med 2009;361:2113-22
   PubMed Web of Science ®Google Scholar
• O'Keefe JH, Bybee KA, Lavie CJ. Intensive lipid intervention in the post-ENHANCE era. Mayo Clin Proc 2008;83:867-9
   PubMed Web of Science ®Google Scholar
• Padial LR. The ENHANCE trial: analysis and clinical significance. Clin Lipidol 2010;5:161-6
   Web of Science ®Google Scholar