Amino acids with affinity for the α2δ-protein

Details Amino acids with affinity for the α2δ-protein Amino acids with affinity for the α2δ-protein

2007-02-20

2007-02-20

Saeed, Kamal A. (Department: 1626)

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

Organic compounds

Carboxylic acid esters

C560S125000, C560S041000

Reexamination Certificate

active

10949907

ABSTRACT:
Certain β-amino acids that bind to the alpha-2-delta (α2δ) subunit of a calcium channel are disclosed. These compounds and their pharmaceutically acceptable salts are useful in the treatment of a variety of psychiatric, pain and other disorders. Also disclosed are methods of making the β-amino acids.

REFERENCES:
patent: 2003/0195251 (2003-10-01), Barta et al.
Gedey, S. et al, “Preparation of highly enantiopure β-amino esters byCandida antarcticalipase A”, Tetrahedron: Asymmetry, (2001), pp. 105-110, vol. 12(1).
Arvantis et al., Enantioselective synthesis of 2-substitured 3-aminopropanoic acid (Beta-alanine) derivatives which are Beta-analogues of aromatic amino acids, J. Chem. Soc., Perkin Trans. 1, (1998), pp. 521-528.
Bull S.D. et al, “Asymmetric Synthesis of Beta-amino Acid Scaffolds”, J. Chem Soc., Perkin Trans. 1, (2001), pp. 2931-2938, vol. 22.
Davies, S.G. et al, “Asymmetric Synthesis of Beta-Phenylalanine, Alpha-Methyl-Beta-Phenylalanines and Derivatives”, J. Chem. Soc., Chem. Commun., (1993), pp. 1153-1155.
Davies, S. G., et al, “A Succinct Asymmetric Synthesis of (2S,3R)-2-Methyl-3-aminopentanoic Acid Hydrochloride”, SYNLETT, (1994), pp. 117-118.
Davis, F.A. et al., “Concise Asymmetric Synthesis of Alpha-Amino Acid Derivatives from N-Sulfinylimino Esters,” J. Org. Chem., (1999), pp. 3396-3397, vol. 64.
Davis, F.A. et al., “Improved Synthesis of Enantiopure Sulfinimines (Thiooxime S-Oxides) from p-Toluenesulfinamide and Aldehydes and Ketones,” J. Org. Chem. (1999), pp. 1403-1406, vol. 64.
Dixon, W. J., W., “Efficient Analysis of Experimental Observations”, Ann. Rev. Pharmacol. Toxicol., (1980), pp. 441-462, vol. 20.
Evans, D. A. et al, “A General Method for the Synthesis of Enantiomerically Pure Beta-Substituted, Beta-Amino Acids through Alpha-Substituted Succinic Acid Derivatives”, J. Org. Chem., (1999), pp. 6411-6417, vol. 64.
Gee, N. S. et al, “The Novel Anticonvulsant Drug, Gabapentin (Neurontin), Binds to the Alpha2Beta Subunit of a Calcium Channel”, J. Biol. Chem., (1996), pp. 5768-5776, vol. 271(10).
Hargreaves, K. et al, “A New and Sensitive Method for Measuring Thermal Nociception in Cutaneous Hyperalgesia”, PAIN, (1988), pp. 77-88, vol. 32.
Hawkins J. et al., Asymmetric Michael Reactions of 3,5-Dihydro-4H-dinaphth[2,1-c:1′,2′-e]azepine with Methyl Crotonate, J.Org.Chem., (1986), pp. 2820-2822, vol. 51.
Hintermann T. et al., “A Useful Modification of the Evans Auxilliary: 4-Isopropyl-5,5-diphenyloxazolidin-2-one,” Helvetica Chimica Acta, (1998), pp. 2093-2126, vol. 81.
Ho, G.J. et al, “Lithium-Initiated Imide Formation. A Simple Method for N-Acylation of 2-Oxazolidinones and Bornane-2, 1—Sultam”, J. Org. Chem., (1995), pp. 2271-2273, vol. 60.
Ishikawa et al, “Chiral Lewis Acid-Hydroxylamine Hybrid Reagent for Enantioselective Michael Addition Reaction Directed Towards Beta-Amino Acids Synthesis”, SYNLETT, (1998), pp. 1291-1293, vol. 11.
Juaristi, E., “Enantioselective Synthesis of beta-Amino Acids”, Tetrahedron: Asymmetry, (1996), pp. 2233-2246, vol. 7, No. 8.
Myers, A. G. et al., “Highly Practical Methodology for the Synthesis of D- and L-Alpha-Amino Acids, N-Protected Alpha-Amino Acids, and N-Methyl-Alpha-Amino Acids,” J. Am. Chem. Soc., (1997), pp. 656-673, vol. 119.
Nagula, G. et al., “Synthesis of Alpha-Substituted Beta-Amino Acids Using Pseudoephedrine as a Chiral Auxiliary,” Org. Letters, (2000), pp. 3527-3529, vol. 2.
Palomino E., “Delivery of Drugs Through Dihydropyridine Carriers”, Drugs of the Future, (1990), pp. 361-368, vol. 15(4).
Randall L.O., et al, “A Method for Measurement of Analgesic Activity On Inflamed Tissue”, Arch. Int. Pharmacodyn., (1957), pp. 409-419, vol. 4.
Seebach, D. et al, “EPC—Synthesis of Beta-Amino Acid Derivatives through Lithiated Hydropyrimidines” Eur: J. Org. Chem., (1999), pp. 335-360.
Sibi, M.P. et al., “A New Methodology for the Synthesis of Beta-Amino Acids”, J. Chem. Soc., Perkin Trans.1, (2000), pp. 1461-1466, vol. 9.
Sluka, K., et al., “Unilateral Intramuscular Injections of Acidic Saline Produce a Bilateral Long-Lasting Hyperalgesia”, Muscle Nerve, (2001), pp. 37-46, vol. 24.
Tang, T. P. et al, “The tert-Butanesulfinyl Group: An Ideal Chiral Directing Group and Boc-Surrogate for the Asymmetric Synthesis and Applications of Beta-Amino Acids”, J. Org. Chem., (1999), pp. 12-13, vol. 64.
Vogel, J.R. et al, “A Simple and Reliable Conflict Procedure for Testing Anti-Anxiety Agents”, Psychopharmacologia, (1971, pp. 1-7, vol. 21.
Yuen P. W. et al, “Enantioselective Synthesis of PD144723: A Potent Stereospecific Anticonvulsant”, Bioorganic & Med. Chem Lett., (1994), pp. 823-825, vol. 4(6).

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