Organic compounds -- part of the class 532-570 series – Organic compounds – Azides
Patent
1995-04-12
1997-03-04
Shippen, Michael L.
Organic compounds -- part of the class 532-570 series
Organic compounds
Azides
548229, 548230, 558 52, 560179, 560190, 560193, 562561, 562567, 562568, 562840, C07C24700
Patent
active
056080905
ABSTRACT:
A compound of the formula ##STR1## wherein R.sub.1 is a straight or branched alkyl group having from 1 to 6 carbon atoms, phenyl, or cycloalkyl having from 3 to 6 carbon atoms; R.sub.2 is hydrogen or methyl; and R.sub.3 is hydrogen, methyl or carboxyl; which is useful in the treatment of seizure disorders. Processes are disclosed for the preparation of the compound. Intermediates prepared during the synthesis of the compound are also disclosed.
REFERENCES:
patent: 4479005 (1984-10-01), Kleschick
Butterworth et al., "Phosphate-activated glutaminase in relation to Huntington's disease and agonal state" J. Neurochemistry, 41:440-447 (1983).
Carvajal et al., "Anticonvulsive action of substances designed as inhibitors of .gamma.-Aminobutyric . . . " Biochem. Pharmacol., 13:1059-1069 (1964).
Chadwick, "Gabapentin" in Recent Advances in Epilepsy, vol. 5, Pedley, T A, Meldrum, B S, eds. Churchill Livingston, NY (1991).
Corey and Suggs, "Pyridinium chlorochromate, an efficient reagent for oxidation of primary and secondary alcohols . . . " Tetrahedron Letters, 31:2647-2650 (1975).
Evans et al., "Enantioselective Michael Reactions. Diastereoselective reactions of chlorotitanium enolates . . . " J. Org. Chem., vol. 56, No. 20:5750-53 (1991).
Evans et al., "Assignment of stereochemistry in the oligomycin/rutamycin/cytovaricin family of antibiotics . . . " J. Org. Chem., 55:6260-6268 (1990).
Evans et al., "Asymmetric diels-alder cycloaddition reactions with chiral .alpha.,.beta.-unsaturated N-acyloxazolidinones" J. Am. Chem. Soc., 110:1238-1256 (1988).
Evans and Weber, "Synthesis of the cyclic hexapeptide echinocandin D. New approaches to the asymmetric synthesis . . . " J. Am. Chem. Soc., 109:7151-7157 (1987).
Evans et al., "Asymmetric synthesis of anti-.beta.-hydroxy-.alpha.-amino acids" Tetrahedron Letters, vol. 28, No. 1, pp. 39-42 (1987).
Evans et al., "Asymmetric halogenation of chiral imide enolates. A general approach to the synthesis . . . " Tetrahedron Letters, vol. 28, No. 11, pp. 1123-1126 (1987).
Evans et al., "Asymmetric alkylation reactions of chiral imide enolates. A practical approach . . . " J. Am. Chem. Soc., 104:1737-1739 (1982).
Hayashi, "The inhibitory action of .beta.-hydroxy-.gamma.-aminobutyric acid upon the seizure following stimulation . . . " Phyiol. (London), 145:570-578 (1959).
Janssens de Varebeke et al., "Effect of milacemide, a gylcinamide derivative, on the rat brain . . . " Biochem. Pharmacol., 32:2751-2755 (1983).
Kaplan et al., "New anticonvulsants: Schiff bases of .gamma.-aminobutyric acid and .gamma.-aminobutyramide" J. Med. Chem., 23:702-704 (1980).
Karlsson et al., "Effect of the convulsive agent 3-mercaptopropionic acid on the levels of gaba, other amino acids . . . " Biochem. Pharmacol., 23:3053-3061 (1974).
Krall et al., "Antiepileptic drug development: II. Anticonvulsant drug screening" Epilepsia, 19:409-428 (1978).
Kim and Cocolas, "Glutamic acid analogs. The synthesis of 3-alkylglutamic acids . . . " J. Med. Chem., 8:509-513 (1965).
Loscher, "Anticonvulsant and biochemical effects of inhibitors of gaba aminotranserase and valproic acid . . . " Biochem. Pharmacol., 31:837-842 (1982).
McGeer et al., in Glutamine, Glutamate and Gaba in the Central Nervous System, Hertz L, Kvamme E, McGeer E B, Schousbal A., eds. Alan R. Liss, Inc., NY, pp. 3-17 (1983).
McGeer et al., in GABA in Nervous System Function, Roberts E, Chase T N, et al., eds. Raven Press, New York, pp. 487-495 (1976).
Phillips and Fowler, "The effects of sodium valproate on .gamma.-aminobutyrate metabolism and behavior in naive . . . " Biochem. Pharmacol., 31:2257-2261 (1982).
Piredda et al., "Effect of stimulus intensity on the profile of anticonvulsant activity of phenytoin, ethosuximide and valproate" Pharmacol. and Exptl. Therap., 232(3):741-45 (1985).
Purpura et al., "Structure-activity determinants of pharmacological effects of amino acids and related compounds on central synapses" J. Neurochemistry, 3:238-268 (1959).
Shashoua et al., "Aliphatic and steroid esters of .gamma.-aminobutyric acid" J. Med. Chem., 27:660-664 (1984).
Spokes, "GABA in Huntington's chorea, parkinsonism and schizophrenia" Adv. Exp. Med. Biol., 123:461-473 (1978).
Wu et al., "Abnormalities of neurotransmitter enzymes in Huntington's chorea" Neurochem. Res., 4:575-586 (1979).
Gage and Evans, "Diastereoselective aldol condensation using a chiral oxazolidinone auxiliary . . . " Org. Synth., 68:83-91 (1990).
Andruszkiewicz Ryszard
Franklin Lloyd C.
Schwindt Mark A.
Silverman Richard B.
Sobieray Denis M.
Northwestern University
Shippen Michael L.
Warner-Lambert & Company
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