Anticonvulsant and anxiolytic lactam and thiolactam derivatives

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...

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548543, A01N 4336, C07D20712

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active

060666668

ABSTRACT:
This invention relates to lactam and thiolactam derivatives having useful anticonvulsant and anxiolytic activity, pharmaceutical compositions containing these compounds and therapeutic applications using such compositions.

REFERENCES:
patent: 3000878 (1961-09-01), Phillips et al.
patent: 3065237 (1962-11-01), Bortnick et al.
patent: 3228955 (1966-01-01), Hickner et al.
patent: 3278526 (1966-10-01), Louthan et al.
patent: 3306910 (1967-02-01), Louthan et al.
patent: 3332938 (1967-07-01), Mayhew et al.
patent: 3346566 (1967-10-01), Chiddex et al.
patent: 3454558 (1969-07-01), Stahl et al.
patent: 3531471 (1970-09-01), Hartwimmer et al.
patent: 3536699 (1970-10-01), Brachel et al.
patent: 3634346 (1972-01-01), McKeon et al.
patent: 3754088 (1973-08-01), Witzel
patent: 4198514 (1980-04-01), Imanishi et al.
patent: 4420568 (1983-12-01), Wang
patent: 4707491 (1987-11-01), Covey et al.
patent: 5010079 (1991-04-01), Manoury et al.
Adams et al. (Sep. 20, 1959) "The Absolute configuration of the C.sup.1 Atom in Retronecanone (1-Methyl-7-oxopyrrolizidine)," J. Am. Chem. Soc. 81:4946-4951.
Baker et al., (1967) "The Synthesis of 3,3-Diethylpiperid-2-one," J. Chem.Soc.,(C), 2148.
Bentz et al. (1987), "Intramolecular Radical Trapping In "Set" Ring Opening of N-Enoyl Aziridines. A New Mechanistic Probe and A New Synthesis of Pyrrolidones," Tetrahedron Lett., 28(22):2511-2512.
Bodine et al. (1982), "An Efficient Conversion of N-Alkyllactams To N-Alkylthiolactams.sup.1," Syn. Communications, 12(10):787-793.
Brunner et al. (1951), "Uber das 3-Athylpyrrolidin and einige Derivate," Mohatsh. 82:371-376.
Canney et al. (1991), "Synthesis and Structure-Activity Studies of Alkyl-Substituted .gamma.-Butyrolactones and .gamma.-Thiobutyrolactones: Ligands for the Picrotoxin Receptor," J. Med. Chem., 34:1460-1467.
Colombo et al. (1991), "Chemoenzymatic Synthesis of the Enantiomers of Iopanoic Acid," Tetrahedron: Asymmetry 2(10):1021-1030.
Cummings et al. (1963), "The Synthesis and Rearrangement of 3-Vinyl-2-pyrrolidone," British Nylon Spinners Ltd., Research Department, Pontypool, Monmouthsire, UK, pp. 4591-4604.
Ferrendelli et al. (1989), "Comparison of the Anticonvulsant Activities of Ethosuximide, Valproate, and a New Anticonvulsant, Thiobutyrolactone," Epilepsia, 30(5):617-622.
Geurtis et al. (1977), "2-Pyrrolidinones," Chem.Abst., vol. 86, 29622r, p350.
Hamill et al. (1981), "Improved Patch-Clamp Techniques for High-Resolution Current Recording from Cells and Cell-Free Membrane Patches," Pflugers Arch. 391:85-100.
Holland et al. (1990), "Binding Interactions of Convulsant and Anticonvulsant .gamma.-Butyrolactones and .gamma.-Thiobutyrolactones with the Picrotoxin Receptor.sup.1, " J. Pharmac. Exp. Therapeutics, 254(2):578-583.
Holland et al. (1990), "Physiological Regulation of the Picrotoxin Receptor by .gamma.-Butyrolactones and .gamma.-Thiobutyrolactones in Cultured Hippocampal Neurons," J. Neurosci., 10(6):1719-1727.
Holland et al. (1990), ".gamma.-Butyrolactone Antagomism of the Picrotoxin Receptor: Comparison of a Pure Antagonist and a Mixed Antagonist/Inverse Agonist," Mol. Pharmacology, 39:79-84.
Holland et al. (1992), "Relative Anticonvulsant Effects of GABAmimetic and GABA Modulatory Agents," Epilepsia, 33(6):981-986.
Kametani et al. (1970), "The Alkaloids of Corydalis pallida var. tenuis (Yatabe) and the Structures of Pallidine and Kikemanine," J. Am. Chem. Soc., (C) pp. 1060-1064.
Khoukhi et al. (1987), "Synthesis and Reactivity of Methyl .gamma.-Azido Butyrates and Ethyl .delta.-Azido Valerates and of the Corresponding Acid Chlories As Useful Reagents for the Amionoalkylation," Tetrahedron, 43(8):1811-1822.
Klunk et al. (1982), "Structure-Activity Relationships of Alkyl-Substituted .gamma.Butyrolactones and Succinimides," Mol. Pharm., 22:444-450.
Koelsch, C.F. (1943), "A Synthesis of 3-Alkylpiperidones," J. Am. Chem. Soc. 65:2458-2459.
Kricheldorf, H.R. (1975), Reaktionen mit Silylaziden, 7, Die Makromolekulare Chemic, 176:57-79.
Levine et al. (1986), "Alkyl-Substituted Thiolo-, Thiono-, and Dithio-.gamma.-butyrolactones: New Classes of Convulsant and Anticonvulsant Agents," J. Med.Chem. 29:1996-1999.
Lion et al.(1981), "Alkylation of some carbonyl compounds by tertiary alkyl groups. Utilization of the Friedel-Crafts reaction in the synthesis of sterically crowded esters and ketones," Tetrahedron, 37:319-323.
Lister, R.G. (1987), "The use of a plus-maze to measure anxiety in the mouse," Psychopharm. 92:180-185.
Loscher et al. (1994) "Strategies in antiepileptic drug development: is rational drug design superior to random screening and structural variation?" Epilepsy Research, 17:95-134.
Menezea et al. (1988), "A Mild and Facile Route to .omega.-Amino Esters," Syn. Comm., 18(14):1625-1636.
Meyers et al. (1987), "Conformational Effects on the Regiochemical Metalation of C.sub.5 -C.sub.13 N-Benzyllactams," J. Am. Chem. Soc. 109: 4405-4407.
Porter,R.J. and Meldrum, B.S. (1992), "Antiepeleptic drugs" Basic & Clinical Pharmacology, Katzung, B.G., Ed., Appleton & Lange, Norwalk, CT, 5th Ed., pp. 331-349.
Potts et al. (1993), "Intramolecular 1,4-Dipolar Cycloaddition of Cross-Conjugated Heterocyclic Betaines. A New Route to Hexahydrojulolidines and Related Peri-Fused Ring Systems," J. Org.Chem. 58:5040-5042.
Quast et al. (1986), "Photochemical formation of methylenecyclopropane analogs. XII. Synthesis of 3,5,5-trialkyl-3,5-dihydro-4H-1,2,3-triazol-4-ones," Liebigs Ann. Chem. pp. 1891-1899.
Rodriguez et al. (1992), "Carba" peptide bond surrogates. Different approaches to Gly-.psi.(CH.sub.2 -CH.sub.2)-D,L-Xaa pseudo-dipeptide units. Int.J.Peptide Protein Res., 39:273-277.
Sinnrich et al. (1968). "The Light-Induced Addition of 2-Pyrrolidone To Olefins," Tetrahedron, 24:4509-4516.
Spencer et al. (1986), "Ynenol Lactones: Synthesis and Investigation of Reactions Relevant to Their Inactivation of Serine Proteases," J. Am. Chem. Soc., 108:5589-5597.
Stamm et al. (1981), "Reactions with aziridines. XXII. One step synthesis of pyrrolidones by amidoethylation of simple esters with N-acylaziridines," Chem. Ber. 114:32-48.
Swinyard et al. (1982), "Experimental Detection, Quantification, and Evaluation of Anticonvulsants," Antiepileptic Drugs, Woodbury, Pentry and Pippenger, eds., Raven Press, NY, pp. 111-126.
Trevor, A.J. and Way. W.L. (1992), "Sedative-hypnotics" Basic & linical Pharmacology, Katzung, B.G., Ed., Appleton & Lnage, Norwalk, CT, 5th Ed., pp. 306-319.
Werry et al. (1989), "Reactions with aziridines. Part 50. Homolytic Aziridine Opening (Aza Variant of Cyclopropylcarbinyl-Homoallyl Rearrangement) By Addition of Tributylin Radical to N-Acylaziridines. Factors Contributing To The Regioselectivity.sup.1," Tetrahedron, 45(16):5015-5028.
Yamaguchi et al. (1985), "A Direct Synthesis of [(tert-Butoxycarbonyl)methylidene]azacycloalkanes from N-Alkyl Lactams," J. Org. Chem. 50:1975-1977.
Yoon, Kong-Woo et al. (1990), "Modulation of the Picrotoxin Receptor by Fluorinated Ethyl, Methyl-Butyrolactones.sup.1," J. Pharm. Exp. Ther, 255(1):248-255.
Callery, P.S. et al. (1984), "Biosynthesis of 5-Aminopentanoic Acid and 2-Piperidone from Cadaverine and 1-Piperidone in Mouse," J. Neurochem. 43:(6):1631-1634.
Jackman, L.M. et al. (1982), J. Org. Chem., pp. 1824-1831.
Laycock, G.M. et al. (1963) Nature, pp. 849-851.
Holland, K.D. et al. (1993), "Alkyl-substituted .gamma.-butyrolactones act at a distinct site allosterically linked tothe TBPS/picrotoxinin site on the GABA.sub.A receptor complex," Brain Res. 615:170-174.
Kircheldorf, H.R. (1975), "Reactions with silylazides. 7. Trimethylsilyl 4-isocyanato-carboxylates and 4-aminocarboxylic acid N-carboxylic acid anhydrides," Makromol. Chem. 176:57-79.

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