An improved kilogram-scale preparation of atorvastatin calcium

Chemistry Central Journal

Volumn 9, Issue 1, 2015, Pages

  Novozhilov, Yuri V ^a   Dorogov, Mikhail V ^a   Blumina, Maria V ^a   Smirnov, Alexey V ^a   Krasavin, Mikhail ^b  

^a YAROSLAVL STATE PEDAGOGICAL UNIVERSITY   (Russian Federation)

^b ST PETERSBURG STATE UNIVERSITY   (Russian Federation)

Author keywords

Atorvastatin; Ester hydrolysis; Ethyl acetate solubility; Hemi calcium salt; Ketal deprotection

Indexed keywords

EID: 84923554365     PISSN: None     EISSN: 1752153X     Source Type: Journal    
DOI: 10.1186/s13065-015-0082-7     Document Type: Article

References (15)

1. Roth BD. The discovery and development of atorvastatin, a potent novel hypolipidemic agent. Prog Med Chem. 2002;40:1-22.
2. Farmer JA. Aggressive lipid therapy in the statin era. Prog Cardiovasc Dis. 1998;41:71-94.
3. Ledford H. Blockbuster drug bows out. Nature. 2011;480:16-7.
4. Vital and Essential Drugs List, 2012-Russian Federation 2012; 136 pages; http://apps.who.int/medicinedocs/documents/s19766ru/s19766ru.pdf.
5. Roth BD, Blankley CJ, Chucholowski AW, Ferguson E, Hoefle ML, Ortwine DF, et al. Inhibitors of cholesterol biosynthesis. 3. Tetrahydro-4-hydroxy-6-[2-(1Hpyrrol- 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;34:357-66.
6. Roth BD. The discovery and development of atorvastatin, a potent novel hypolipidemic agent. Prog Med Chem. 2002;40:1-22.
7. Estévez V, Villacampa M, Menéndez JC. Concise synthesis of atorvastatin lactone under high-speed vibration milling conditions. Org Chem Front. 2014;1:458-63.
8. Brower PL, Butler DE, Deering CF, Le TV, Millar A, Nanninga TN, et al. 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;33:2279-82.
9. Suri S, Sarin GS. A process for the synthesis of large particle size statin compounds. PCT Int Appl WO2006048893A2. Chem Abstr. 2006;144:456528.
10. Antoncic L, Sorsak G, Copar A. Process for the preparation of amorphous calcium salt of atorvastatin. PCT Int Appl WO2004089895A1. Chem Abstr. 2004;141:878372.
11. Aronhime J, Lidor-Hadas R, Niddam-Hildesheim V, Wizel S, Lifshitz-Liron R, Pinchasov M. Novel crystal forms of atorvastatin hemi-calcium. US Pat Appl US20070265456A1. Chem Abstr. 2007;147:1308606.
12. Agarwal VK, Vakil MH, Pandita K, Ramakrishna NVS, Patel PR, Manakiwala SC. Process for the production of atorvastatin calcium in amorphous form. PCT Int Appl WO2002083638A1. Chem Abstr. 2002;137:814099.
13. Niddam-Hildesheim V, Lifshitz-Liron R, Lidor-Hadas R. Processes for preparing calcium salt forms of statins. PCT Int Appl 2003016317A1. Chem Abstr. 2003;138:154436.
14. Stimac A, Zupet R, Grcman M, Smrkolj M, Jakse R. Polymorphs of atorvastatin tert-butyl ester and use as intermediates for the preparation of atorvastatin. PCT Int Appl WO2005097742A1. Chem Abstr. 2005;143:410952.
15. Gudipati S, Katkam S, Komati S, Kudavalli SJ. Amorphous atorvastatin calcium. PCT Int Appl 2006039441A1. Chem Abstr. 2006;144:376507.