Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acids and salts thereof
Patent
1995-04-12
1997-11-04
Shippen, Michael L.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acids and salts thereof
C07C20500
Patent
active
056841892
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: 2628980 (1953-02-01), Moe
patent: 3634509 (1972-01-01), Yates
patent: 4077941 (1978-03-01), Stephen
patent: 4243678 (1981-01-01), Krastinat
patent: 4322440 (1982-03-01), Fish
patent: 4814342 (1989-03-01), Hoover
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, TA, Meldrum, BS, 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 glycinamide 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 EB, Schousbal A., eds. Alan R. Liss, Inc., NY, pp.3-17 (1983).
McGeer et al., in GABA in Nervous System Function, Roberts E, Chase TN, 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).
Pollini, Synthesis, pp. 44-45, 1975.
Ono, Synthesis, pp. 226-227, 1984.
Rathki, J. Am. Chem. Soc., vol. 92, pp. 3222-3223, 1970.
Carson, J. Org. Chem., vol. 20, pp. 1591-1601, 1955.
Colonge, Bull. Soc. Chim., Fr., pp. 598-603, 1962.
Andruszkiewicz, Synthesis, pp. 953-603 (received by PTO Jan. 18, 1990), 1989.
Andruszkiewicz, Journal of Biological Chemistry, vol. 265, pp. 22288-22291, Dec. 25, 1990.
Allinger, "Organic Chemistry," pp. 532-537, 1971.
Andruszkiewicz Ryszard
Franklin Lloyd Charles
Schwindt Mark Alan
Silverman Richard B.
Sobieray Denis Martin
Northwestern University
Shippen Michael L.
Warner-Lambert & Company
LandOfFree
GABA and L-glutamic acid analogs for antiseizure treatment does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with GABA and L-glutamic acid analogs for antiseizure treatment, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and GABA and L-glutamic acid analogs for antiseizure treatment will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-1834338