Login Register Cart 0
Generic placeholder image

Current Medicinal Chemistry

Editor-in-Chief

ISSN (Print): 0929-8673
ISSN (Online): 1875-533X

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe Translate in Chinese
Review Article

Recent Advances in the Synthesis and Analysis of Atorvastatin and its Intermediates

Author(s): Shu-Fang Li, Wei Zhang, Wen Zhang, An Huang, Jia-Qi Zhu, Ya-Jun Wang* and Yu-Guo Zheng

Volume 31, Issue 37, 2024

Published on: 11 October, 2023

Page: [6063 - 6083] Pages: 21

DOI: 10.2174/0109298673263728231004053704

Price: $65

Open Access Journals Promotions 2
Abstract

Atorvastatin, a lipid-lowering drug that is widely used in the treatment of cardiovascular diseases, has significant clinical significance. This article focuses on the synthetic procedures of atorvastatin, including Paal-Knorr synthesis and several new synthetic strategies. It also outlines chemical and chemo-enzymatic methods for synthesizing optically active side chain of atorvastatin. In addition, a comprehensive overview of the analytical monitoring techniques for atorvastatin and its metabolites and impurities is reported, alongside a discussion of their strengths and limitations.

Keywords: Atorvastatin, lipid-lowering drug, HMG-CoA, statins, Paal-Knorr synthesis, analytical methods.

« Previous Next »
[1]
White, A.A. Mapping and geographic display of data. Stat. Med., 1995, 14(5-7), 697-699.
[http://dx.doi.org/10.1002/sim.4780140529] [PMID: 7540768]
[2]
Townsend, N.; Kazakiewicz, D.; Lucy Wright, F.; Timmis, A.; Huculeci, R.; Torbica, A.; Gale, C.P.; Achenbach, S.; Weidinger, F.; Vardas, P. Epidemiology of cardiovascular disease in Europe. Nat. Rev. Cardiol., 2022, 19(2), 133-143.
[http://dx.doi.org/10.1038/s41569-021-00607-3] [PMID: 34497402]
[3]
Liljeblad, A.; Kallinen, A.; Kanerva, L. Biocatalysis in the preparation of the statin side chain. Curr. Org. Synth., 2009, 6(4), 362-379.
[http://dx.doi.org/10.2174/157017909789108738]
[4]
Libby, P. The changing landscape of atherosclerosis. Nature, 2021, 592(7855), 524-533.
[http://dx.doi.org/10.1038/s41586-021-03392-8] [PMID: 33883728]
[5]
Bakker-Arkema, R. A brief review paper of the efficacy and safety of atorvastatin in early clinical trials. Atherosclerosis, 1997, 131(1), 17-23.
[http://dx.doi.org/10.1016/S0021-9150(97)06066-8]
[6]
Grundy, S.M. Summary of the second report of the national cholesterol education program (NCEP) expert panel on detection, evaluation, and treatment of high blood cholesterol in adults (adult treatment panel II). JAMA, 1993, 269(23), 3015-3023.
[http://dx.doi.org/10.1001/jama.1993.03500230097036] [PMID: 8501844]
[7]
Society, E.A. Prevention of coronary heart disease: Scientific background and new clinical practice guidelines. Nutr. Metab. Cardiovasc. Dis., 1992, 2, 113-156.
[8]
Rosamond, W.D.; Chambless, L.E.; Folsom, A.R.; Cooper, L.S.; Conwill, D.E.; Clegg, L.; Wang, C.H.; Heiss, G. Trends in the incidence of myocardial infarction and in mortality due to coronary heart disease, 1987 to 1994. N. Engl. J. Med., 1998, 339(13), 861-867.
[http://dx.doi.org/10.1056/NEJM199809243391301] [PMID: 9744969]
[9]
Kannel, W.B.; Castelli, W.P.; Gordon, T.; McNamara, P.M. Serum cholesterol, lipoproteins, and the risk of coronary heart disease. The Framingham study. Ann. Intern. Med., 1971, 74(1), 1-12.
[http://dx.doi.org/10.7326/0003-4819-74-1-1] [PMID: 5539274]
[10]
Austin, M.A. Plasma triglyceride and coronary heart disease. Arterioscler. Thromb., 1991, 11(1), 2-14.
[http://dx.doi.org/10.1161/01.ATV.11.1.2] [PMID: 1987999]
[11]
Hulley, S.B.; Rosenman, R.H.; Bawol, R.D.; Brand, R.J. Epidemiology as a guide to clinical decisions. The association between triglyceride and coronary heart disease. N. Engl. J. Med., 1980, 302(25), 1383-1389.
[http://dx.doi.org/10.1056/NEJM198006193022503] [PMID: 7374696]
[12]
Pedersen, T.R. Randomised trial of cholesterol lowering in 4444 patients with coronary heart disease: The scandinavian simvastatin survival study (4S). Lancet, 1994, 344(8934), 1383-1389.
[PMID: 7968073]
[13]
Ferri, N.; Corsini, A. Clinical pharmacology of statins: An update. Curr. Atheroscler. Rep., 2020, 22(7), 26.
[http://dx.doi.org/10.1007/s11883-020-00844-w] [PMID: 32494971]
[14]
Corsini, A.; Maggi, F.M.; Catapano, A.L. Pharmacology of competitive inhibitors of HMg-CoA reductase. Pharmacol. Res., 1995, 31(1), 9-27.
[http://dx.doi.org/10.1016/1043-6618(95)80042-5] [PMID: 7784310]
[15]
Azemawah, V.; Movahed, M.R.; Centuori, P.; Penaflor, R.; Riel, P.L.; Situ, S.; Shadmehr, M.; Hashemzadeh, M. State of the art comprehensive review of individual statins, their differences, pharmacology, and clinical implications. Cardiovasc. Drugs Ther., 2019, 33(5), 625-639.
[http://dx.doi.org/10.1007/s10557-019-06904-x] [PMID: 31773344]
[16]
Moghadasian, M.H. Experimental atherosclerosis: A historical overview. Life Sci., 1999, 65, 1329.
[http://dx.doi.org/10.1016/S0024-3205(99)00199-X] [PMID: 10503952]
[17]
Khan, T.J.; Ahmed, Y.M.; Zamzami, M.A.; Siddiqui, A.M.; Khan, I.; Baothman, O.A.S.; Mehanna, M.G. kuerban, A.; Kaleemuddin, M.; Yasir, M. Atorvastatin treatment modulates the gut microbiota of the hypercholesterolemic patients. OMICS, 2018, 22(2), 154-163.
[http://dx.doi.org/10.1089/omi.2017.0130] [PMID: 29432061]
[18]
Haque, T.; Khan, B.V. Atorvastatin: A review of its pharmacological properties and use in familial hypercholesterolemia. Clin. Lipidol., 2010, 5(5), 615-625.
[http://dx.doi.org/10.2217/clp.10.55]
[19]
Nawrocki, J.W.; Weiss, S.R.; Davidson, M.H.; Sprecher, D.L.; Schwartz, S.L.; Lupien, P.J.; Jones, P.H.; Haber, H.E.; Black, D.M. Perfusion, 1996, 9(3), 109-114.
[20]
Best, J.D.; Nicholson, G.C. Atorvastatin and simvastatin reduce elevated cholesterol in non-insulin dependent diabetes. Diabetes Nutr. Metab., 1996, 9, 74-80.
[21]
Ionica, F.E.; Pisoschi, C.; Negres, S.; Nikos, R.F.; Tarata, M.; Popescu, F. Atorvastain influence om glycemic control in patients with type 2 diabetes mellitus. Farmacia, 2010, 58(6), 728-734.
[22]
Kougialis, S.; Skopelitis, E.; Gialernios, T.; Nikolaou, S.; Kroustalis, A.; Katsadorou, E.; Gialernios, K.; Zervou, A.; Gika, E.; Polydorou, A.; Polydorou, V.; Drakoulis, C.; Iliopoulos, N.; Dermitzakis, I.; Mpilinis, H.; Polydorou, A. Atorvastatin therapy is associated with improvement of oxidized low-density lipoprotein cholesterol levels, which correlates with the degree of stenosis in patients with carotid atheromatosis with and without prior angioplasty. Int. J. Angiol., 2010, 29(4), 338-347.
[PMID: 20671652]
[23]
Malhotra, H.S.; Goa, K.L. Atorvastatin. Drugs, 2001, 61(12), 1835-1881.
[http://dx.doi.org/10.2165/00003495-200161120-00012] [PMID: 11693468]
[24]
Koh, K.K.; Quon, M.J.; Han, S.H.; Lee, Y.; Park, J.B.; Kim, S.J.; Koh, Y.; Shin, E.K. Additive beneficial effects of atorvastatin combined with amlodipine in patients with mild-to-moderate hypertension. Int. J. Cardiol., 2011, 146(3), 319-325.
[http://dx.doi.org/10.1016/j.ijcard.2009.07.002] [PMID: 19651449]
[25]
Jones, P.H.; Goldberg, A.C.; Knapp, H.R.; Kelly, M.T.; Setze, C.M.; Stolzenbach, J.C.; Sleep, D.J. Efficacy and safety of fenofibric acid in combination with atorvastatin and ezetimibe in patients with mixed dyslipidemia. Am. Heart J., 2010, 160(4), 759-766.
[http://dx.doi.org/10.1016/j.ahj.2010.06.045] [PMID: 20934572]
[26]
Chawla, P.A.; Pandey, S. Various analytical methods for analysis of atorvastatin: A review. J. Drug Deliv. Ther., 2019, 9(3-s), 885-899.
[27]
Kogawa, A.C.; Pires, A.E.D.T.; Salgado, H.R.N. Atorvastatin: A review of analytical methods for pharmaceutical quality control and monitoring. J. AOAC Int., 2019, 102(3), 801-809.
[http://dx.doi.org/10.5740/jaoacint.18-0200] [PMID: 30563586]
[28]
Chong, P.H.; Seeger, J.D. Atorvastatin calcium: An addition to HMG-CoA reductase inhibitors. Pharmacotherapy, 1997, 17(6), 1157-1177.
[PMID: 9399600]
[29]
Althanoon, Z.; Faisal, I.M.; Ahmad, A.A.; Merkhan, M.M.; Merkhan, M.M. Pharmacological aspects of statins are relevant to their structural and physicochemical properties. Syst. Rev. Pharm, 2020, 11(7), 167-171.
[30]
Nováková, L.; Šatínský, D.; Solich, P. HPLC methods for the determination of simvastatin and atorvastatin. Trends Analyt. Chem., 2008, 27(4), 352-367.
[http://dx.doi.org/10.1016/j.trac.2008.01.013]
[31]
Hirota, T.; Fujita, Y.; Ieiri, I. An updated review of pharmacokinetic drug interactions and pharmacogenetics of statins. Expert Opin. Drug Metab. Toxicol., 2020, 16(9), 809-822.
[http://dx.doi.org/10.1080/17425255.2020.1801634] [PMID: 32729746]
[32]
Zaheer, Z.; Farooqui, M.N.; Mangle, A.A.; Nikalje, A.G. Stability-indicating high performance liquid chromatographic determination of atorvastatin calcium in pharmaceutical dosage form. Afr. J. Pharm. Pharmacol., 2008, 2(10), 204-210.
[33]
Hoffmann, M.; Nowosielski, M. DFT study on hydroxy acid-lactone interconversion of statins: The case of atorvastatin. Org. Biomol. Chem., 2008, 6(19), 3527-3531.
[http://dx.doi.org/10.1039/b803342k] [PMID: 19082153]
[34]
Lennernäs, H. Clinical pharmacokinetics of atorvastatin. Clin. Pharmacokinet., 2003, 42(13), 1141-1160.
[http://dx.doi.org/10.2165/00003088-200342130-00005] [PMID: 14531725]
[35]
Kolars, J.C.; Lown, K.S.; Schmiedlin-Ren, P.; Ghosh, M.; Fang, C.; Wrighton, S.A.; Merion, R.M.; Watkins, P.B. CYP3A gene expression in human gut epithelium. Pharmacogenetics, 1994, 4(5), 247-259.
[http://dx.doi.org/10.1097/00008571-199410000-00003] [PMID: 7894497]
[36]
Lau, Y.Y.; Okochi, H.; Huang, Y.; Benet, L.Z. Multiple transporters affect the disposition of atorvastatin and its two active hydroxy metabolites: Application of in vitro and ex situ systems. J. Pharmacol. Exp. Ther., 2006, 316(2), 762-771.
[http://dx.doi.org/10.1124/jpet.105.093088] [PMID: 16258024]
[37]
Harrington, P.J. Pharmaceutical process chemistry for synthesis: Rethinking the routes to scale-up; John Wiley & Sons, 2011.
[38]
Roth, B.D.; Arbor, A. Trans-6-[2-(3- or 4-carboxamidosubstituted pyrrol-1-yl)alkyl]-4-hydroxypyran-2-one inhibitors of cholesterol synthesis. U.S. Patent 4681893A, 1987.
[39]
Roth, B.D.; Arbor, A. [R-(R* R*)]-2-(4-fluorophenyl-β, δ- dihydroxy-5-(1-methylethyl-3-phenyl-4-[(phenylamino) carbonyl]-1H-pyrrole-1-heptanoic acid, its lactone form and salts thereof. U.S. Patent 5273995, 1993.
[40]
Ye, J.; Liu, Y.; Li, C.L. Method for preparing atorvastatin calcium. C.N. Patent 101613312A, 2009.
[41]
Roth, B.D.; Blankley, C.J.; Chucholowski, A.W.; Ferguson, E.; Hoefle, M.L.; Ortwine, D.F.; Newton, R.S.; Sekerke, C.S.; Sliskovic, D.R.; Wilson, M. Inhibitors of cholesterol biosynthesis. 3. Tetrahydro-4-hydroxy-6-[2-(1H-pyrrol-1-yl)ethyl]-2H-pyran 2-one inhibitors of HMG-CoA reductase. 2. Effects of introducing substituents at positions three and four of the pyrrole nucleus. J. Med. Chem., 1991, 34(1), 357-366.
[http://dx.doi.org/10.1021/jm00105a056] [PMID: 1992137]
[42]
Guntoori, B.R.; Che, D.; Wang, F.; Zhao, Y.; Murthy, K.S.K.; Horne, S.E. An improved preparation of atorvastatin. W.O. Patent 087723A1, 2005.
[43]
Guntoori, B.R.; Che, D.; Zhao, Y.; Murthy, K.S.K.; Horne, S.E. Preparation of atorvastatin. U.S. Patent 0203302A1, 2005.
[44]
Bell, E.L.; Finnigan, W.; France, S.P.; Green, A.P.; Hayes, M.A.; Hepworth, L.J.; Lovelock, S.L.; Niikura, H.; Osuna, S.; Romero, E.; Ryan, K.S.; Turner, N.J.; Flitsch, S.L. Biocatalysis. Nat. Rev. Methods Primers, 2021, 1(1)
[45]
Hoyos, P.; Pace, V.; Alcántara, A. Biocatalyzed synthesis of statins: A sustainable strategy for the preparation of valuable drugs. Catalysts, 2019, 9(3), 260.
[http://dx.doi.org/10.3390/catal9030260]
[46]
Butler, D.E.; Dejone, R.L.; Nelson, J.D. Novel process for the synthesis of 5-(4-fluorophenyl)-1-[2-((2R,4R)-4- hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-2-isopropyl-4- phenyl-1H-pyrrole-3-carboxylic acid phenylamide. U.S. Patent 20020133026A1, 2002.
[47]
Fleige, M.; Glorius, F. α-unsubstituted pyrroles by NHC-catalyzed three-component coupling: Direct synthesis of a versatile atorvastatin derivative. Chemistry, 2017, 23(45), 10773-10776.
[http://dx.doi.org/10.1002/chem.201703008] [PMID: 28666059]
[48]
Baumann, K.L.; Butler, D.E.; Deering, C.F.; Mennen, K.E.; Millar, A.; Nanninga, T.N.; Palmer, C.W.; Roth, B.D. The convergent synthesis of CI-981, an optically active, highly potent, tissue selective inhibitor of HMG-CoA reductase. Tetrahedron Lett., 1992, 33(17), 2283-2284.
[http://dx.doi.org/10.1016/S0040-4039(00)74190-6]
[49]
Butler, D.E. Process for trans-6-[2-(substituted-Pyrrol-1-yl) alkyl] pyran-2-one inhibitors of cholesterol synthesis. U.S. Patent 5298627, 1994.
[50]
Woo, P.W.K.; Hartman, J.; Huang, Y. Atorvastatin, an HMG-CoA reductase inhibitor and efficient lipid-regulation agent. J. Labelled Comp. Radiopharm., 1999, 42(2), 121-127.
[http://dx.doi.org/10.1002/(SICI)1099-1344(199902)42:2<121:AID-JLCR173>3.0.CO;2-Z]
[51]
Niddam, V.; Hadas, R.L.; Lifshitz, R.; Ishai, E. Hydrolysis of [R-(R* R*)]-2-(4-fluorophenyl-β, δ-dihydroxy-5-(1- methylethyl-3-phenyl-4-[(phenylamino) carbonyl]-1Hpyrrole- 1-heptanoic acid esters with calcium hydroxide. U.S. Patent 6528661, 2003.
[52]
Chen, B.C.; Sundeen, J.E.; Guo, P.; Bednarz, M.S.; Hangeland, J.J.; Ahmed, S.Z.; Jemal, M. Synthesis of deuterium-labeled atorvastatin and its metabolites for use as internal standards in a LC/MS/MS method developed for quantitation of the drug and its metabolites in human serum. J. Labelled Comp. Radiopharm., 2000, 43(3), 261-270.
[http://dx.doi.org/10.1002/(SICI)1099-1344(20000315)43:3<261:AID-JLCR312>3.0.CO;2-T]
[53]
Stach, J.; Havlíček, J.; Plaček, L.; Rádl, S. Synthesis of some impurities and/or degradation products of atorvastatin. Collect. Czech. Chem. Commun., 2008, 73(2), 229-246.
[http://dx.doi.org/10.1135/cccc20080229]
[54]
Amarnath, V.; Amarnath, K.; Amarnath, K.; Davies, S.; Roberts, L.J. II Pyridoxamine: An extremely potent scavenger of 1,4-dicarbonyls. Chem. Res. Toxicol., 2004, 17(3), 410-415.
[http://dx.doi.org/10.1021/tx0300535] [PMID: 15025512]
[55]
Patel, D.J.; Kumar, R.; Dwivedi, S.P.D. Process for the preparation of atorvastatin calcium. W.O. Patent 096751A1, 2007.
[56]
Valerie, N.H.; Revital, L.L.; Rami, L.H. Process for preparing calcium salt forms of statins. U.S. Patent 6777552B2, 2004.
[57]
Sullivan, S.O.; Neill, J.O. Preparation of an atorvastatin intermediate. U.S. Patent 0221839A1, 2009.
[58]
Thottathil, J.K.; Pendri, Y.; Li, W.S.; Kronenthal, D.R. Process for the preparation of 1, 3-dioxane derivatives useful in the preparation of HMG-CoA reductase inhibitors. U.S. Patent 5278313, 1994.
[59]
Thottathil, J.K.; Pendri, Y.; Li, W.S.; Kronenthal, D.R. Process for the preparation of 1, 3-dioxane derivatives useful in the preparation of HMG-CoA reductase inhibitors. U.S. Patent 5457227, 1995.
[60]
Brower, P.L.; Butler, D.E.; Deering, C.F.; Le, T.V.; Millar, A.; Nanninga, T.N.; Roth, B.D. The synthesis of (4R-cis)-1,1-dimethylethyl 6-cyanomethyl-2,2-dimethyl-1,3-dioxane- 4-acetate, a key intermediate for the preparation of CI-981, a highly potent, tissue selective inhibitor of HMG-CoA reductase. Tetrahedron Lett., 1992, 33(17), 2279-2282.
[http://dx.doi.org/10.1016/S0040-4039(00)74189-X]
[61]
Rádl, S. A New Way to tert -Butyl [(4 R, 6R)-6-Aminoethyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate, a key intermediate of atorvastatin synthesis. Synth. Commun., 2003, 33(13), 2275-2283.
[http://dx.doi.org/10.1081/SCC-120021507]
[62]
Li, Z.; Yang, H.; Liu, J.; Huang, Z.; Chen, F. Application of ketoreductase in asymmetric synthesis of pharmaceuticals and bioactive molecules: An update (2018-2020). Chem. Rec., 2021, 21(7), 1611-1630.
[http://dx.doi.org/10.1002/tcr.202100062] [PMID: 33835705]
[63]
Butler, D.E.; Deering, C.F.; Millar, A.; Nanninga, T.N.; Roth, B.D. Process for trans-6-[2-(substituted-pyrrol-1- yl)alkyl]pyran-2-one inhibitors of cholesterol synthesis. U.S. Patent 5245047, 1993.
[64]
Rádl, S.; Stach, J.; Hajicek, J. An improved synthesis of 1,1-dimethylethyl 6-cyanomethyl-2,2-dimethyl-1,3-dio-xane-4-acetate, a key intermediate for atorvastatin synthesis. Tetrahedron Lett., 2002, 43(11), 2087-2090.
[http://dx.doi.org/10.1016/S0040-4039(02)00175-2]
[65]
Thomas, T.; Poornaprajna, A.; Aswathanarayanappa, C.; Sridharan, M.; Ganesh, S. Process for stereoselective recution of β-ketoesters. U.S. Patent 7232920B2, 2007.
[66]
Bosch, R.L.; Mscabe, R.J.; Nanninga, T.N.; Stach, R.J. Process for the synthesis of 1, 3-diols. U.S. Patent 7232915B2, 2007.
[67]
Kooistra, J.H.M.H.; Zeegers, H.J.M.; Mink, D.; Mulders, J.M.C.A. Process for the preparation of 2-(6-substituted-1, 3-dioxane-4-yl) acetic acid derivatives. W.O. Patent 06266A1, 2002.
[68]
Mitsuda, M.; Miyazaki, M.; Inoue, K. Process for producing 6-caynomethyl-1, 3-dioxane-4-acetic acid derivatives. U.S. Patent 6344569B1, 2002.
[69]
Xiong, F.J.; Li, J.; Chen, X.F.; Chen, W.X.; Chen, F.E. An improved process for chiron synthesis of the atorvastatin side chain. Tetrahedron Asymmetry, 2014, 25(16-17), 1205-1208.
[http://dx.doi.org/10.1016/j.tetasy.2014.07.002]
[70]
Patel, J.M. Biocatalytic synthesis of atorvastatin intermediates. J. Mol. Catal., B Enzym., 2009, 61(3-4), 123-128.
[http://dx.doi.org/10.1016/j.molcatb.2009.07.004]
[71]
Kizaki, N.; Yamada, Y.; Yasohara, Y.; Nishiyama, A.; Miyazaki, M.; Mitsuda, M.; Kondo, T.; Ueyama, N.; Inoue, K. Process for producing optically active 2-[6- (hydroxymethyl)-1, 3-dioxan-4-yl] acetic acid derivatives. U.S. Patent 0040634A1, 2003.
[72]
Yasohara, Y.; Kizaki, N.; Hasegawa, J.; Wada, M.; Kataoka, M.; Shimizu, S. Stereoselective reduction of alkyl 3-oxobutanoate by carbonyl reductase from Candida magnoliae. Tetrahedron Asymmetry, 2001, 12(12), 1713-1718.
[http://dx.doi.org/10.1016/S0957-4166(01)00279-8]
[73]
Kizaki, N.; Yasohara, Y.; Hasegawa, J.; Wada, M.; Kataoka, M.; Shimizu, S. Synthesis of optically pure ethyl (S)-4-chloro-3-hydroxybutanoate by Escherichia coli transformant cells coexpressing the carbonyl reductase and glucose dehydrogenase genes. Appl. Microbiol. Biotechnol., 2001, 55(5), 590-595.
[http://dx.doi.org/10.1007/s002530100599] [PMID: 11414326]
[74]
Wolberg, M.; Filho, M.V.; Bode, S.; Geilenkirchen, P.; Feldmann, R.; Liese, A.; Hummel, W.; Müller, M. Chemoenzymatic synthesis of the chiral side-chain of statins: Application of an alcohol dehydrogenase catalysed ketone reduction on a large scale. Bioprocess Biosyst. Eng., 2008, 31(3), 183-191.
[http://dx.doi.org/10.1007/s00449-008-0205-9] [PMID: 18288496]
[75]
Wolberg, M.; Hummel, W.; Müller, M. Biocatalytic reduction of β,δ-diketo esters: A highly stereoselective approach to all four stereoisomers of a chlorinated β,δ-dihydroxy hexanoate. Chemistry, 2001, 7(21), 4562-4571.
[http://dx.doi.org/10.1002/1521-3765(20011105)7:21<4562:AID-CHEM4562>3.0.CO;2-4] [PMID: 11757647]
[76]
Liu, J.; Hsu, C.C.; Wong, C.H. Sequential aldol condensation catalyzed by DERA mutant Ser238Asp and a formal total synthesis of atorvastatin. Tetrahedron Lett., 2004, 45(11), 2439-2441.
[http://dx.doi.org/10.1016/j.tetlet.2004.01.110]
[77]
Greenberg, W.A.; Varvak, A.; Hanson, S.R.; Wong, K.; Huang, H.; Chen, P.; Burk, M.J. Development of an efficient, scalable, aldolase-catalyzed process for enantioselective synthesis of statin intermediates. Proc. Natl. Acad. Sci., 2004, 101(16), 5788-5793.
[http://dx.doi.org/10.1073/pnas.0307563101] [PMID: 15069189]
[78]
Davis, S.C.; Grate, J.H.; Gray, D.R.; Gruber, J.M.; Huisman, G.W.; Ma, S.K.; Newman, L.M.; Sheldon, R.; Wang, L.A. Enzymatic process for the production of 4-substituted 3-hydroxybutyric acid derivatives and vicinal cyano, hydroxy substituted carboxylic acid esters. W.O. Patent 018579A2, 2005.
[79]
Dicks, P. Green chemistry and associated metrics.Green Chemistry Metrics; Springer: Cham, 2015, pp. 1-15.
[80]
Giver, L.J.; Newman, L.S.; Mundorff, E.; Huisman, G.W.; Jenne, S.J.; Zhu, Z.; Behrouzian, B.; Grate, J.H.; Lalonde, J. Compositions and methods for produing stereoisomerically pure statins and synthetic intermediates therefor. U.S. Patent 0195465A1, 2011.
[81]
Sawant, P.; Maier, M.E. A novel strategy towards the atorvastatin lactone. Tetrahedron, 2010, 66(51), 9738-9744.
[http://dx.doi.org/10.1016/j.tet.2010.10.028]
[82]
Mohammad, S.; Jitendra, S.; Yatendra, K.; Chander, A.R.; Krishna, R.V.; Anita, C. Substituted pyrrole derivatives. W.O. Patent 106299A2, 2004.
[83]
John, M.D.; William, W.J. Process and intermediate compounds useful in the preparation of statins, particularly atorvastatin. W.O. Patent 012246A, 2005.
[84]
Norman, B.D. Novel process for trans-6-[2-(Substituted- Pyrrol-1-Yl)Alkyl]Pyran-2-one inhibitors of cholesterol synthesis. W.O. Patent 1994020492, 1994.
[85]
Tararov, V.; Borner, A.; Konig, G.; Korostylev, A. Method for the production of statins. W.O. Patent 2006122644, 2006.
[86]
Lee, H.W.; Kim, Y.M.; Yoo, C.L.; Kang, S-K.; Ahn, S.K. An efficient method for the large-scale synthesis of atorvastatin calcium. Biomol. Ther., 2008, 16(1), 28-33.
[http://dx.doi.org/10.4062/biomolther.2008.16.1.028]
[87]
Sumitra, S.; Joy, M.; Sandhya, U.; Madhavan, S.; Ganesh, S. A process for the synthesis of atorvastatin form V and phenylboronates as intermediate conmpounds. W.O. Patent 057274A1, 2002.
[88]
Sumitra, S.; Joy, M.; Sandhya, U.; Madhavan, S.; Ganesh, S. Process for the synthesis of atorvastatin form V and phenylboronates as intermediate conmpounds. U.S. Patent 6867306B2, 2005.
[89]
Tararov, V.I.; Andrushko, N.; Andrushko, V.; König, G.; Spannenberg, A.; Börner, A. Synthesis of the chiral side chain of statins - lactone versus lactol pathway. Eur. J. Org. Chem., 2006, 2006(24), 5543-5550.
[http://dx.doi.org/10.1002/ejoc.200600849]
[90]
Baisch, R.Ö. Pyrrole synthesis. W.O. Patent 2003044011, 2002.
[91]
Estévez, V.; Villacampa, M.; Menéndez, J.C. Concise synthesis of atorvastatin lactone under high-speed vibration milling conditions. Org. Chem. Front., 2014, 1(5), 458-463.
[http://dx.doi.org/10.1039/C4QO00052H]
[92]
Menéndez, J.; Leonardi, M.; Estévez, V.; Villacampa, M. The Hantzsch pyrrole synthesis: Non-conventional variations and applications of a neglected classical reaction. Synthesis, 2019, 51(4), 816-828.
[http://dx.doi.org/10.1055/s-0037-1610320]
[93]
Goyal, S.; Patel, B.; Sharma, R.; Chouhan, M.; Kumar, K.; Gangar, M.; Nair, V.A. An efficient strategy for the synthesis of syn 1,3-diols via iterative acetate aldol reactions and synthesis of atorvastatin lactone. Tetrahedron Lett., 2015, 56(40), 5409-5412.
[http://dx.doi.org/10.1016/j.tetlet.2015.08.011]
[94]
Dias, L.C.; Vieira, A.S.; Barreiro, E.J. The total synthesis of calcium atorvastatin. Org. Biomol. Chem., 2016, 14(7), 2291-2296.
[http://dx.doi.org/10.1039/C5OB02546J] [PMID: 26795833]
[95]
Zarganes-Tzitzikas, T.; Neochoritis, C.G.; Dömling, A. Atorvastatin (Lipitor) by MCR. ACS Med. Chem. Lett., 2019, 10(3), 389-392.
[http://dx.doi.org/10.1021/acsmedchemlett.8b00579] [PMID: 30891146]
[96]
Ertürk, S.; Sevinç Aktaş, E.; Ersoy, L.; Fıçıcıoğlu, S. An HPLC method for the determination of atorvastatin and its impurities in bulk drug and tablets. J. Pharm. Biomed. Anal., 2003, 33(5), 1017-1023.
[http://dx.doi.org/10.1016/S0731-7085(03)00408-4] [PMID: 14656592]
[97]
Chaudhari, B.G.; Patel, N.M.; Shah, P.B.; Patel, L.J.; Patel, V.P. Stability-indicating reversed-phase liquid chromatographic method for simultaneous determination of atorvastatin and ezetimibe from their combination drug products. J. AOAC Int., 2007, 90(6), 1539-1546.
[PMID: 18193730]
[98]
Patel, V.; Baldha, R.; Patel, D. Simultaneous determination of atorvastatin calcium and ezetimib by ratio spectra derivative spectrophotometry and reverse phase-high performance liquid chromatography. Asian J. Chem., 2010, 22(4), 2507-2511.
[99]
Chaudhari, B.; Patel, N.; Shah, P. Reverse Phase HPLC method for determination of atorvastatin calcium in plasma. Chem. Pharm. Bull., 2007, 55(2), 241-246.
[http://dx.doi.org/10.1248/cpb.55.241] [PMID: 17268096]
[100]
Mohammadi, A.; Rezanour, N.; Ansari Dogaheh, M.; Ghorbani Bidkorbeh, F.; Hashem, M.; Walker, R.B. A stability-indicating high performance liquid chromatographic (HPLC) assay for the simultaneous determination of atorvastatin and amlodipine in commercial tablets. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci., 2007, 846(1-2), 215-221.
[http://dx.doi.org/10.1016/j.jchromb.2006.09.007] [PMID: 17010681]
[101]
Nirogi, R.; Mudigonda, K.; Kandikere, V. Chromatography–mass spectrometry methods for the quantitation of statins in biological samples. J. Pharm. Biomed. Anal., 2007, 44(2), 379-387.
[http://dx.doi.org/10.1016/j.jpba.2007.02.008] [PMID: 17433599]
[102]
Nováková, L.; Lopéz, S.A.; Solichová, D.; Šatínský, D.; Kulichová, B.; Horna, A.; Solich, P. Comparison of UV and charged aerosol detection approach in pharmaceutical analysis of statins. Talanta, 2009, 78(3), 834-839.
[http://dx.doi.org/10.1016/j.talanta.2008.12.057] [PMID: 19269437]
[103]
Bořek-Dohalský, V.; Huclová, J.; Barrett, B.; Němec, B.; Ulč, I.; Jelínek, I. Validated HPLC-MS-MS method for simultaneous determination of atorvastatin and 2-hydroxyatorvastatin in human plasma-pharmacokinetic study. Anal. Bioanal. Chem., 2006, 386(2), 275-285.
[http://dx.doi.org/10.1007/s00216-006-0655-3] [PMID: 16924379]
[104]
Van Pelt, C.K.; Corso, T.N.; Schultz, G.A.; Lowes, S.; Henion, J. A four-column parallel chromatography system for isocratic or gradient LC/MS analyses. Anal. Chem., 2001, 73(3), 582-588.
[http://dx.doi.org/10.1021/ac0006876] [PMID: 11217766]
[105]
Nirogi, R.V.S.; Kandikere, V.N.; Shukla, M.; Mudigonda, K.; Maurya, S.; Boosi, R.; Anjaneyulu, Y. Simultaneous quantification of atorvastatin and active metabolites in human plasma by liquid chromatography-tandem mass spectrometry using rosuvastatin as internal standard. Biomed. Chromatogr., 2006, 20(9), 924-936.
[http://dx.doi.org/10.1002/bmc.622] [PMID: 16470513]
[106]
Bullen, W.W.; Miller, R.A.; Hayes, R.N. Development and validation of a high-performance liquid chromatography tandem mass spectrometry assay for atorvastatin, ortho-hydroxy atorvastatin, and para-hydroxy atorvastatin in human, dog, and rat plasma. J. Am. Soc. Mass Spectrom., 1999, 10(1), 55-66.
[http://dx.doi.org/10.1016/S1044-0305(98)00118-4] [PMID: 9888185]
[107]
Jemal, M.; Ouyang, Z.; Chen, B.C.; Teitz, D. Quantitation of Atorvastatin and its bio-transformation products in human serum by HPLC with electro spray tandem mass spectrometry. Rapid Communi. Mass Spectrom., 1999, 13, 1003-1015.
[108]
Hermann, M.; Christensen, H.; Reubsaet, J.L.E. Determination of atorvastatin and metabolites in human plasma with solid-phase extraction followed by LC-tandem MS. Anal. Bioanal. Chem., 2005, 382(5), 1242-1249.
[http://dx.doi.org/10.1007/s00216-005-3266-5] [PMID: 15933849]
[109]
Mornar, A.; Damić, M.; Nigović, B. Separation, characterization, and quantification of atorvastatin and related impurities by liquid chromatography-electrospray ionization mass spectrometry. Anal. Lett., 2010, 43(18), 2859-2871.
[http://dx.doi.org/10.1080/00032711003763624]
[110]
Sherma, J. Review of HPTLC in drug analysis: 1996-2009. J. AOAC Int., 2010, 93(3), 754-764.
[http://dx.doi.org/10.1093/jaoac/93.3.754] [PMID: 20629372]
[111]
Shirkhedkar, A.; Surana, S. Simultaneous densitometric TLC analysis of atorvastatin calcium and fenofibrate in the bulk drug and in pharmaceutical formulations. JPC J. Planar Chromatog. Modern TLC, 2009, 22(5), 355-358.
[112]
Hiral, J.; Panchal, B.N.S.; Patel, N.J. Estimation of pitavastatin calcium in tablet dosage forms by column liquid chromatography and ultraviolet spectrophotometry. J. Planar Chromatog., 2009, 22(4), 265-271.
[113]
Hancu, G.; Tomegea, D.; Popescu, G.; Barabas-Hajdu, E. The use of capillary electrophoresis in the simultaneous determination of fixed-dose combination drugs for cardiovascular diseases. Trends Pharmacol. Sci., 2020, 6(3), 221-230.
[114]
Hefnawy, M.M.; Sultan, M.; Al-Johar, H. Development of capillary electrophoresis technique for simultaneous measurement of amlodipine and atorvastatin from their combination drug formulations. J. Liq. Chromatogr. Relat. Technol., 2009, 32(20), 2923-2942.
[http://dx.doi.org/10.1080/10826070903320681]
[115]
Guihen, E.; Sisk, G.D.; Scully, N.M.; Glennon, J.D. Rapid analysis of atorvastatin calcium using capillary electrophoresis and microchip electrophoresis. Electrophoresis, 2006, 27(12), 2338-2347.
[http://dx.doi.org/10.1002/elps.200500899] [PMID: 16786480]
[116]
Landers, J.P. Clinical capillary electrophoresis. Clin. Chem., 1995, 41(4), 495-509.
[http://dx.doi.org/10.1093/clinchem/41.4.495] [PMID: 7720237]
[117]
Nigović, B.; Damić, M.; Injac, R.; Kočevar Glavač, N.; Štrukelj, B. Analysis of atorvastatin and related substances by MEKC. Chromatographia, 2009, 69(11-12), 1299-1305.
[http://dx.doi.org/10.1365/s10337-009-1049-4]
[118]
Sharma, S.; Sharma, M.C. Determination of atorvastatin calcium and pioglitazone HCl in pharmaceutical formulations form by using atomic absorption spectrometry. Optoelectron. Adv. Mater. Rapid Commun., 2010, 4(8), 1196-1199.
[119]
Sánchez Rojas, F.; Bosch Ojeda, C. Recent development in derivative ultraviolet/visible absorption spectrophotometry: 2004-2008. Anal. Chim. Acta, 2009, 635(1), 22-44.
[http://dx.doi.org/10.1016/j.aca.2008.12.039] [PMID: 19200476]
[120]
Ayalon, A.; Levinger, M.; Roytblat, S.; Niddam, V.; Lifshitz, R.; Aronhime, J. Polymorphic form of atorvastatin calcium. U.S. Patent 7411075, 2008.
[121]
Briggs, C.; Jennings, R.; Wade, R.; Harasawa, K.; Ichikawa, S.; Minohara, K.; Nakagawa, S. Crystalline [R-(R*, R*)]-2-(4-Dfluorophenyl)-β,δ-dihydroxy-5-(1-methylethy l)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrole-1- heptanoic acid hemi calcium salt (atorvastatin). U.S. Patent 005969156A, 1999.
[122]
Lee, E.H. A practical guide to pharmaceutical polymorph screening & selection. Asian J. Pharmaceut. Sci., 2014, 9(4), 163-175.
[http://dx.doi.org/10.1016/j.ajps.2014.05.002]
[123]
Skorda, D.; Kontoyannis, C.G. Identification and quantitative determination of atorvastatin calcium polymorph in tablets using FT-Raman spectroscopy. Talanta, 2008, 74(4), 1066-1070.
[http://dx.doi.org/10.1016/j.talanta.2007.07.030] [PMID: 18371751]
[124]
Mazurek, S.; Szostak, R. Quantification of atorvastatin calcium in tablets by FT-Raman spectroscopy. J. Pharm. Biomed. Anal., 2009, 49(1), 168-172.
[http://dx.doi.org/10.1016/j.jpba.2008.10.015] [PMID: 19062220]

Rights & Permissions Print Cite
Article Metrics
54
1
Wayfinder Image
Open Access Journals Promotions
World Antimicrobial Awareness Week
© 2024 Bentham Science Publishers | Privacy Policy