Pregabalin free of lactam and a process for preparation thereof

Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acids and salts thereof

Reexamination Certificate

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Reexamination Certificate

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07488846

ABSTRACT:
The present invention encompasses Pregabalin substantially free of Lactam and a process for obtaining Pregabalin substantially free of Lactam comprising extracting an acidic mixture containing a complex of Pregabalin with a strong mineral acid, with C3-8alcohol; and combining the organic phase with an organic base.

REFERENCES:
patent: 5010189 (1991-04-01), Herold et al.
patent: 5599973 (1997-02-01), Silverman et al.
patent: 5616793 (1997-04-01), Huckabee et al.
patent: 5629447 (1997-05-01), Huckabee et al.
patent: 5637737 (1997-06-01), Andres et al.
patent: 5637767 (1997-06-01), Grote et al.
patent: 6197819 (2001-03-01), Silverman et al.
patent: 6333198 (2001-12-01), Edmeades et al.
patent: 6488964 (2002-12-01), Bruna et al.
patent: 6891059 (2005-05-01), Burk et al.
patent: 6924377 (2005-08-01), Blazecka et al.
patent: 7141695 (2006-11-01), Przewosny et al.
patent: 2001/0016665 (2001-08-01), Grote et al.
patent: 2002/0012679 (2002-01-01), Bruna et al.
patent: 2003/0225149 (2003-12-01), Blazecka et al.
patent: 2005/0222464 (2005-10-01), Hoge, II
patent: 2005/0228190 (2005-10-01), Bao et al.
patent: 2005/0283023 (2005-12-01), Hu et al.
patent: 2006/0270871 (2006-11-01), Khanduri et al.
patent: 2007/0073085 (2007-03-01), Hedvati et al.
patent: 2008/0014280 (2008-01-01), Kumar et al.
patent: 1 634 869 (2005-07-01), None
patent: 297 970 (2007-03-01), None
patent: WO 96/38405 (1996-12-01), None
patent: WO 96/40617 (1996-12-01), None
patent: WO 01/55090 (2001-08-01), None
patent: WO 2005/100580 (2005-10-01), None
patent: WO 2006/000904 (2006-01-01), None
patent: WO 2006/008640 (2006-01-01), None
patent: WO 2006/136087 (2006-12-01), None
patent: WO 2008/004044 (2008-01-01), None
patent: WO 2008/007145 (2008-01-01), None
patent: WO 2008/009897 (2008-01-01), None
Andruszkiewicz and Silverman, “A Convenient Synthesis of 3-Alkyl-4-Aminobutanoic Acids,”Synthesis, 953-955 (1989).
Barnes, D.M., et al., “Development of a Catalytic Enantioselective Conjugate Addition of 1,3-Dicarbonyl Compounds to Nitroalkenes for the Synthesis of Endothelin-A Antagonist ABT-546. Scope, Mechanism, and Further Application to the Synthesis of the Antidepressant Rolipram,”J. Am. Chem. Soc., 124(44): 13097-13105 (2002).
Berner et al. “Asymmetric Michael Additions to Nitroalkenes,”European Journal of Organic Chemistry, 1877-1894 (2002).
Cason, J. et al., “Branched-Chain Fatty Acids. XXVII. Further Study of the Dependence of Rate of Amide Hydrolysis on Substitution near the Amide Group. Relative Rates of Hydrolysis of Nitrile to Amide and Amide to Acid,”J. Org. Chem., 18(9): 1129-1136 (1953).
Chen, AO et al., “Synthesis of Pregabalin,”Zhongguo YiYao Gongye Zazhi, 35(4): 195-196 (2004).
Colonge et al., “Preparation De Pyrrolidones-2 et de Gamma-Aminoacides,”Bulletin De La Societe Chimique De France, Societe Francaise De Chimie, 598-603 (1962).
Day and Thorpe, “The Formation and Reactions of Imino-compounds. Part XX. The Condensation of Aldehydes with Cyanoacetamide,”J. Chem. Soc., 117: 1465-1474 (1920).
Hoekstra, M.S. et al., “Chemical Development of CI-1008, an Enantiomerically Pure Anticonvulsant,”Organic Process Research and Development, 1(1): 26-38 (1997).
Karanewsky, D.S. et al., “Practical Synthesis of an Enantiomerically Pure Synthon for the Preparation of Mevinic Acid Analogues,”J. Org. Chem., 56(11): 3744-3747 (1991).
Li, H. et al., “Highly Enantioselective Catalytic Conjugate Addition of Malonate and β-Ketoester to Nitroalkenes: Asymmetric C-C Bond Formation with New Bifunctional Organic Catalysts Based on Cinchona Alkaloids,”J. Am. Chem. Soc., 126(32): 9906-9907 (2004).
Martin, L. et al., “Pregabalin,”Drugs of the Future, 24(8): 862-870 (1999).
Okino, T. et al., “Enantio- and Diastereoselective Michael Reaction of 1,3-Dicarbonyl Compounds to Nitroolefins Catalyzed by a Bifunctional Thiourea,”J. Am. Chem. Soc., 127(1): 119-125 (2005).
Sammis, G.M. et al., “Highly Enantioselective Catalytic Conjugate Addition of Cyanide to α, β-Unsaturated Imides”,J. Am. Chem. Soc., 125(15): 4442-43 (2003).
Shintani, Ryo et al., “Highly Enantioselective Desymmetrization of Anhydrides by Carbon Nucleophiles: Reactions of Grignard Reagents in the Presence of (−)-Sparteine,”Angewandte Chemie, International Edition, 41(6): 1057-1059 (2002).
Theisen, P.D. et al., “Prochiral Recognition in the Reaction of 3-Substituted Glutaric Anhydrides with Chiral Secondary Alcohols,”J. Org. Chem., 58(1): 142-146 (1993).
Verma, Rekha et al., “Desymmetrization of prochiral anhydrides with Evans' oxazolidinones: an efficient route to homochiral glutaric and adipic acid derivatives,”J. Chem. Soc., Perkin Transactions 1: Organic and Bio-Organic Chemistry, 257-264 (1999).
Yamamoto et al., “Stereoselective Synthesis of (E)-Alkylidenesuccinates by Palladium-catalyzed Carbonylation,”Bull. Chem. Soc. Japan, 58(11): 3397-3398 (1985).
Strobel et al.,Chemical Instrumentation: A Systematic Approach, 3rd Ed., (1989), pp. 391-393, 879-894, 922-925, 953, John Wiley & Sons, Inc.
Snyder et al.,Introduction To Modern Liquid Chromatography, 2ndEd., (1979), pp. 549-572, John Wiley & Sons, Inc.

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