Chiral 3-carbamoylmethyl-5-methyl hexanoic acids, key...

Details Chiral 3-carbamoylmethyl-5-methyl hexanoic acids, key... Chiral 3-carbamoylmethyl-5-methyl hexanoic acids, key...

2007-08-21

2008-12-16

Eyler, Yvonne (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acids and salts thereof

C546S248000, C558S441000, C435S128000

Reexamination Certificate

active

07465826

ABSTRACT:
The invention encompasses the synthesis of (S)-(+)-3-(aminomethyl)-5-methylhexanoic acid, (S)-Pregabalin, via the intermediate, (3R)-5-methyl-3-(2-oxo-2{[(1R)-1-phenylethyl]amino}ethyl)hexanoic acid.

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: 6001876 (1999-12-01), Singh
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: 6580003 (2003-06-01), Deng 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: 2003/0212290 (2003-11-01), Burk 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 2006/000904 (2005-01-01), None
patent: WO 2005/100580 (2005-10-01), 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
Berner et al. “Asymmetric Michael Additions to Nitroalkenes”,European Journal of Organic Chemistry, 1877-1894 (2002).
Cason 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 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 et al., “Chemical Development of CI-1008, an Enantiomerically Pure Anticonvulsant,”Organic Process Research and Development, 1(1): 26-38 (1997).
Karanewsky et al., “Practical Synthesis of an Enantiomerically Pure Synthon for the Preparation of Mevinic Acid Analogues”,J. Org. Chem. 56(11): 3744-3747 (1991).
Shintani 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).
Snyder et al., Introduction To Modern Liquid Chromatography, 549-572, 2ndEd., John Wiley & Sons, Inc. (1979).
Strobel et al., Chemical Instrumentation: A Systematic Approach, 391-393, 879-894, 922-925, 953 (3rdEd., 1989).
Theisen 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 et al., “Desymmetrization of prochiral anhydrides with Evans' oxazolidinones: an efficient route to homochiral glutaric and adipic acid derivatives”,Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry, 257-264 (1999).
Martin et al. “Pregabalin: CI-1008, PD-144723” Drugs of the Future, vol. 24, No. 8, pp. 862-870, (1999).
Yamamoto et al., “Stereoselective Synthesis of (E)-Alkylidenesuccinates by Palladium-catalyzed Carbonylation”, Bull.Chem.Soc.Japan., vol. 58, pp. 3397-3398 (1985).
G. M. Sammis et al., “Highly enantioselective catalytic conjugate addition of cyanide to α,β-unsaturated imides”, J.Am.Chem.Soc., vol. 125, No. 15, pp. 4442-4443 (2003).
Andruszkiewicz and Silverman, “A convenient synthesis of 3-Alkyl-4-aminobutanoic acids”, Synthesis, pp. 953-955 (1989).
H. Li, 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 alkalaids”, J. Am. Chem. Soc., vol. 126, No. 32, pp. 9906-9907 (2004).
D.M. Barnes, 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., vol. 124, No. 44, pp. 13097-13105 (2002).
T. Okino, et al., “Entantio- and Diastereoselective Michael Reaction of 1,3-Dicarbonyl Compounds to Nitroolefins Catalyzed by a Bifunctional Thiourea”, J. Am.Chem.Soc., vol. 127, No. 1, pp. 119-125 (2005).

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