Process for preparing β-amino-α-hydroxycarboxamides

Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing

Reexamination Certificate

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Details

C564S190000, C564S192000, C564S193000, C564S198000, C549S553000

Reexamination Certificate

active

07612237

ABSTRACT:
The present invention is directed to a process for preparing β-amino-α-hydroxycarboxamides. The process works with epoxycarboxamides of the formula 2which are reacted with ammonia or other amines.

REFERENCES:
patent: 3538158 (1970-11-01), Becke et al.
patent: 6025516 (2000-02-01), Ramaswamy
patent: 6057473 (2000-05-01), Sharpless
patent: 7034178 (2006-04-01), Faber
patent: 2003/0153788 (2003-08-01), Kobayashi
patent: 2005/0153900 (2005-07-01), Velazquez
patent: 2005/0197301 (2005-09-01), Njoroge
patent: 583 243 (1933-08-01), None
patent: WO-95/00535 (1995-01-01), None
patent: WO 98/42657 (1998-10-01), None
patent: WO-98/42657 (1998-10-01), None
patent: WO-01/74768 (2001-10-01), None
patent: WO-02/18369 (2002-03-01), None
patent: WO 03/087075 (2003-10-01), None
patent: WO 2005/058821 (2005-06-01), None
patent: WO-2005/082892 (2005-09-01), None
patent: WO-2005/087731 (2005-09-01), None
patent: WO-2006/008170 (2006-01-01), None
patent: WO 2007/105729 (2007-09-01), None
patent: WO 2007/109023 (2007-09-01), None
patent: WO 2007/138928 (2007-12-01), None
Bols et al., Acta Chemica Scandinavica, 45, 1991, 280-284.
Fourneau et al., Mémoires présentés à la société chimique, 1940, 7(54), 593-603.
English language translation for Fourneau et al., Mémoires présentés à la société chimique, 1940, 7(54), 593-603.
European Search Report for EP 07 11 0343 filed Sep. 20, 2007.
Avakyan, et al., “Oxygen-Containing Heterocycles. Part XVIII. Synthesis and Antiarrhythmic Activity of N-[1-(1,4-Benzodioxan-2-YL)Ethyl]Amides of N-Substituted α-Hydroxy-β-Aminopropionic Acids,”Pharmaceutical Chemistry Journal31(4):178-181 (1997).
Banfi, et al., “Passerini Reaction-Amine Deprotection-Acyl Migration (PADAM): A Convenient Strategy for the Solid-Phase Preparation of Peptidomimetic Compounds,”Molecular Diversity6:227-235 (2003).
Behrens, et al., “Selective Transformations of 2,3-Epoxy Alcohols and Related Derivatives. Strategies for Nucleophilic Attack at Carbon-3 or Carbon-2,”J. Org. Chem. 50:5696-5704 (1985).
Cacciola, et al., “The Synthesis of Lysine α-Ketomide Thrombin Inhibitors via an Epoxy Amide Ring Opening,”Tetrahedron Letters38:5741-5744 (1977).
Catalano, et al. “Design of Small Molecular Ketoamide-Based Inhibitors of Cathepsin K,”Bioorg. Med. Chem. Lett. 14:719-722 (2004).
Chen, et al., “Potent 7-Hydroxy-1,2,3,4-Tetrahydroisoquinoline-3-Carboxylic Acid-Based Macrocyclic Inhibitors of Hepatitis C Virus NS3 Protease,”J. Med. Chem. 49:567-574 (2006).
Chen, et al., “Novel Potent Hepatitis C Virus NS3 Protease Inhibitors Derived from Proline-Based Macrocycles,”J. Med. Chem. 49:995-1005 (2006).
Chen, et al., “P1 and P1′ Optimization of [3,4]-Bicycloproline P2 Incorporated Tetrapeptidyl α-Ketoamide Based HCV Protease Inhibitors,”Lett. Drug Design&Discovery2:118-123 (2005).
Chong, et al., “Nucleophilic Openings of 2,3-Epoxy Acids and Amides Mediated by Ti(O-i-Pr)4. Reliable C-3 Selectivity,”J. Org. Chem. 50:1560-1563 (1985).
Kamandi, et al.,“Die Synthese von β-Phenyl-isoserinen durch Ammonolyse von β-Phenylglycidestern, II,”Arch. Pharm. 308:135-147 (1975).
Liwschitz, et al., “Syntheses of α-Amino-βhydroxy-acids,”J. Chem. Soc. 1116-1119(1961).
Ohshima, et al., “Catalytic Asymmetric Epoxidation of α,β-Unsaturated Carboxylic Acid Imidazolides and Amides by Lanthanide-Binol Complexes,”Tetrahedron59:10485-10497(2003).
Punniyamurthy, et al., “Polyaniline Supported Cobalt(II) Salen Catalysed Synthesis of Pyrrolidine Containing α-Hydroxyamide Core Structures as Inhibitors for HIV Proteases,”Tetrahedron Lett. 38(25): 4463-4466 (1997).
Rubin, et al., “A Highly Efficient Aminohydroxylation Process,”Angew Chem. Intl. Ed. Engl. 36(23): 2637-2640 (1997).
Tack, et al., “Unterscheidung N-substituierter 3-Phenylserin-und 3-Phenylisoserin-Derivate,”Arch. Pharm. 312: 138-147 (1979).
English language translation for reference B8 (DE 583 243) cited above.
English abstract and machine translation of WO 2007/105729, listed as reference B4 above.
English language translation of claims for WO 2007/105729, listed as reference B4 above.
English language abstract for WO 2007/138928, listed as reference B6 above.
English translation of patent claims for WO 2007/138928, listed as reference B6 above.
Hoskins, et al., “A Hexaimidazole Ligand Binding Six Octahedral Metal Ions to Give an Infinite 3D α-Po-Like Network Through Which Two Independent 2D Hydrogen-Bonded Networks Interweave,”Angew. Chem. Int. Ed. Engl. 36(24):2752-2755 (1997).
Kato, et al., “Regio- and Stereo-specific Synthesis of threo-3-Amino-2-hydroxy-Acids, Novel Amino-acids contained in Aminopeptidase Inhibitors of Microbial Origin,”J.C.S. Perkin I: 1618-1621 (1980).
English language translation for reference B8 (DE 583 243) cited above, (1933).

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