Asymmetric synthesis of...

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

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

Reexamination Certificate

active

07851651

ABSTRACT:
(S)-Pregabalin, which has the chemical name (S)-(+)-3-(aminomethyl)-5-methylhexanoic acid, is useful in anticonvulsant therapy, primarily due a mechanism that serves to promote the production of gamma-amino butyric acid, an inhibitory neurotransmitter. The invention encompasses new processes for synthesizing (S)-Pregabalin. The invention also comprises certain new compounds that are useful synthetic intermediates in the synthesis of (S)-Pregabalin.

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: 6187930 (2001-02-01), Torrens-Jover 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: 6580003 (2003-06-01), Deng et al.
patent: 6642398 (2003-11-01), Belliotti et al.
patent: 6797730 (2004-09-01), Xiang et al.
patent: 6833458 (2004-12-01), Liu et al.
patent: 6891059 (2005-05-01), Burk et al.
patent: 6924377 (2005-08-01), Blazecka et al.
patent: 6927036 (2005-08-01), Gallop et al.
patent: 6942876 (2005-09-01), Magnus-Miller et al.
patent: 7022678 (2006-04-01), Hurley et al.
patent: 7141695 (2006-11-01), Przewosny et al.
patent: 7462738 (2008-12-01), Hedvati et al.
patent: 2001/0016665 (2001-08-01), Grote et al.
patent: 2002/0012679 (2002-01-01), Bruna et al.
patent: 2003/0212290 (2003-11-01), Burk et al.
patent: 2003/0225149 (2003-12-01), Blazecka et al.
patent: 2005/0070483 (2005-03-01), Donevan et al.
patent: 2005/0222464 (2005-10-01), Hoge, II
patent: 2005/0228190 (2005-10-01), Bao et al.
patent: 2005/0250818 (2005-11-01), Koike et al.
patent: 2005/0267170 (2005-12-01), Koike et al.
patent: 2005/0283023 (2005-12-01), Hu et al.
patent: 2006/0128765 (2006-06-01), Wood et al.
patent: 2006/0183791 (2006-08-01), Khanzhin et al.
patent: 2006/0270871 (2006-11-01), Khanduri et al.
patent: 2007/0073085 (2007-03-01), Hedvati et al.
patent: 2007/0135356 (2007-06-01), Scheuerman et al.
patent: 2007/0191636 (2007-08-01), Kansal et al.
patent: 2008/0014280 (2008-01-01), Kumar et al.
patent: 2008/0311635 (2008-12-01), Riva 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 03/020273 (2003-03-01), 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 2006/110783 (2006-10-01), None
patent: WO 2006/121557 (2006-11-01), None
patent: WO 2006/122255 (2006-11-01), None
patent: WO 2006/136087 (2006-12-01), None
patent: WO 2007/100086 (2007-09-01), 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
patent: WO 2008/040935 (2008-04-01), None
patent: WO 2008/062460 (2008-05-01), None
patent: WO 2008/118427 (2008-10-01), None
patent: WO 2009/010554 (2009-01-01), None
Liu et al., 12 Tetrahedron: Asymmetry, 419-26 (2001).
Morissette et al. Advanced Drug Delivery Reviews 2004, 56, 275-300.
Vippagunta et al., Advanced Drug Delivery Reviews 2001, 48, 3-26, abstract.
Andruszkiewicz et al., “A Convenient Synthesis of 3-Alkyl-4-Aminobutanoic Acids”, Synthesis, pp. 953-955 (1989).
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).
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 et al., “Synthesis of Pregabalin”, Zhongguo Yiyao Gongye Zazhi, vol. 35, No. 4, pp. 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, Marvin S. et al., “Chemical Development of CI-1008, an Enantiomerically Pure Anticonvulsant”, Organic Process Research & Development, vol. 1, No. 1, pp. 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., vol. 56, No. 11, pp. 3744-3747 (1991).
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 Alkaloids”, J. Am. Chem. Soc., vol. 126, No. 32, pp. 9906-9907 (2004).
Martin, L. et al., “Pregabalin,”Drugs of the Future, 24(8): 862-870 (1999).
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).
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).
Shintani et al., “Highly enantioselective desymrnetrization of anhydrides by carbon nucleophiles: reactions of Grignard reagents in the presence of (−)-sparteine”, Angewandte Chemie, International Edition, vol. 41, No. 6, pp. 1057-1059 (2002).
Snyder et al., Introduction to Modern Liquid Chromatography, 549-572 (2d ed., John Wiley & Sons, 1979).
Strobel et al., Chemical Instrumentation: A Systematic Approach, 391-393, 879-894, 922-925, 953 (3d ed. 1989).
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 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, No. 3, pp. 257-264 (1999).
Yamamoto et al., “Stereoselective Synthesis of (E)-Alkylidenesuccinates by Palladium-catalyzed Carbonylation”, Bull.Chem.Soc.Japan., vol. 58, No. 11 pp. 3397-3398 (1985).
US Office Action, dated Oct. 25, 2007, from related U.S. Appl. No. 11/523,865, filed Sep. 19, 2006.
Boots et al., “Hypocholesterolemic Agents VII: Inhibition of β-Hydroxy-βmethylglutaryl-CoA Reductase by Monoesters of Substituted Glutaric Acids”,Journal of Pharmaceutical Sciences, 69(5), 506-509 (1980).
Burk et al., “An Enantioselective Synthesis of (S)-(+)-3-Aminomethyl-5-methylhexanoic Acid via Asymmetric Hydrogenation”,J. Org. Chem., 68(14): 5731-5734 (2003).
Elinson et al., “Electrochemical Cyclization of Tetramethyl Esters of 2-Substituted Propane-1, 1, 3, 3-Tetracarboxylic Acids in the Presence of Salts of Hydrohalic Acids”,lzvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 12, 2783-2789 (1990).
Hiratake et al., “Enantiotopic-group Differentiation. Catalytic Asymmetric Ring-opening of Prochiral Cyclic Acid Anhydrides with Methanol, using Cinchona Alkaloids”,Journal of the Chemical Society, Perkin Trans. 1, 1053-1058 (1987).
Knoevenagel, “Condensationen zwischen Malonester und Aldehyden unter

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Asymmetric synthesis of... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Asymmetric synthesis of..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Asymmetric synthesis of... will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-4196781

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.