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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546216, 546243, A01N 4340

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active

057769591

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: 3228955 (1966-01-01), Hickner et al.
patent: 3278526 (1966-10-01), Louthan et al.
patent: 3306910 (1967-02-01), Louthan et al.
patent: 3346566 (1967-10-01), Chiddix 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: 4707491 (1987-11-01), Covey et al.
patent: 5010079 (1991-04-01), Manoury et al.
Laycock, G.M. et al, Nature, 1963, 200, pp. 849-851.
Jackman, L.M. et al, J. Org. Chem. 1982, 47, pp. 1824-1831.
Callery, P.S. et al, "Biosynthesis of 5-Aminopentanoic Acid and 2-Piperidone from Cadaverine and 1-Piperidone in Mouse" J. Neurochem. 1984, 43(6), pp. 1631-1634, abstract only.
Levine et al., "Alkyl-Substituted Thiolo-, Thiono-, and Dithio-.gamma.-butyrolactones: New Classes of Convulsant and Anticonvulsant Agents," J. of Med.Chem. 29, 1986, 1996-1999.
Ferrendelli et al., "Comparison of the Anticonvulsant Activities of Ethosuximide, Valproate, and a New Anticonvulsant, Thiobutyrolactone," Epilepsia, 30(5):617-622,, 1989, 617-622.
Holland et al., "Binding Interactions of Convulsant and Anticonvulsant .gamma.-Butyrolactones and .gamma.-Thiobutyrolactones with the Picrotoxin Receptor.sup.1," J. of Pharmac. and Exp. Therapeutics, 254, No. 2, 1990., 578-583.
Holland et al., "Physiological Regulation of the Picrotoxin Receptor by .gamma.-Butyrolactones and .gamma.-Thiobutyrolactones in Cultured Hippocampal Neurons," J. of Neurosci,, 10(6), 1990, 1719-1727.
Holland et al., ".gamma.-Butyrolactone Antagonism of the Picrotoxin Receptor: Comparison of a Pure Antagonist and a Mixed Antagonist/Inverse Agonist," Molecular Pharmacology, 39:79-84, 1990.
Yoon, Kong-Woo et al., "Modulation of the Picrotoxin Receptor by Fluorinated Ethyl, Methyl-Butyrolactones.sup.1," J. of Pharmac. and Experimantal Therapeutics, 255, No. 1, 1990, 248-255.
Canney et al., "Synthesis and Structure-Activity Studies of Alkyl-Substituted .gamma.-Butyrolactones and .gamma.-Thiobutyrolactones: Ligands for the Picrotoxin Receptor," J. of Med. Chem., 34, 1991, 1460-1467.
Holland et al., "Relative Anticonvulsant Effects of GABAmimetic and GABA Modulatory Agents," Epilepsia, 33(6):981-986, 1992.
Klunk et al., "Structure-Activity Relationships of Alkyl-Substituted .gamma.Butyrolactones and Succinimides," Molecular Pharm., 22:444-450, 1982.
Baker et al., "The Synthesis of 3,3-Diethylpiperid-2-one," J.Amer.Chem.Soc., (C), 1967, 2148.
Menezea et al., "A Mild and Facile Route to .omega.-Amino Esters," Synth. Comm., 18(14), 1988, 1625-1636.
Khoukhi et al., "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, No. 8, 1987, 1811-1822.
Adams et al., "The Absolute configuration of the C.sup.1 Atom in Retronecanone (1-Methyl-7-oxopyrrolizidine)," vol. 81, Sep. 20, 1959.
Kametani et al., "The Alkaloids of Corydalis pallida var. tenuis (Yatabe) and the Structures of Pallidine and Kikemanine," J.Amer.Chem.Soc., (C) 1970, 1060-1064.
Cummings et al., "The Synthesis and Rearrangement of 3-Vinyl-2-pyrrolidone," British Nylon Spinners Ltd., Research Department, Pontypool, Monmouthsire, UK, 1963, 4591-4604.
Geurtis et al., "2-Pyrrolidinones," Chem.Abst., vol. 86, 1977, p.350.
Sinnreich et al., "The Light-Induced Addition of 2-Pyrrolidone To Olefins," Tetrahedron, vol. 24, 1968, 4509-4516.
Bentz et al., "Intramolecular Radical Trapping In Set Ring Opening of N-Enoyl Aziridines. A New Mechanistic Probe and A New Synthesis of Pyrrolidones," Tetrahedron Lett., vol. 28,No. 22, 1987, 2511-2512.
Werry et al., "Homolytic Aziridine Opening (Aza Variant of Cyclopropylcarbinyl-Homoallyl Rearrangement) By Addition of Tributyltin Radical to N-Acylaziridines. Factors Contributing To The Regioselectivity.sup.1," Tetrahedron, vol. 45, No. 16, 1989, 5015-5028.
Stamm et al., "Einstufensynthese von Pyrrolidonen durch Amidoethylierung einfacher Ester mit N-Acylaziridinen," Chem. Ber. 114, 1981, 32-48.
Kricheldorf, H.R., Reaktionen mit Silylaziden, 7, Die Makromolekulare Chemic, 176, 1975, 57-79.
Koelsch, C.F. "A Synthesis of 3-Alkylpiperidones," vol. 65, 2093, 1943.
Rodriguez et al., "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, 1992, 273-277.
Wang et al., "Fluorescent polarization immunoassay utilizing substituted triazinylaminofluoresceins," Chem.Abst., vol. 100, 1984, p. 290.
Bodine et al., "An Efficient Conversion of N-Alkyllactams to N-Alkylthiolactams.sup.1," Syn. Communications, 12(10), 1982, 787-793.
Potts et al., "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, 1993, 5040-5042.
Lion et al., "Alkylation de Quelques Composes Carbonyles Par Des Groupes Teritiaires, Utilisation de la Reaction de Friedel-Crafts Dans La Syntheese D Esters et de Cetones Encombres," Tetrahedron, vol. 37, 1981, 319-323.
Spencer et al., "Ynenol Lactones: Synthesis and Investigation of Reactions Relevant to Their Inactivation of Serine Proteases," J. Am. Chem. Soc., 108, 1986, 5589-5597.
Colombo et al., "Chemoenzymatic Synthesis of the Enantiomers of Iopanoic Acid," Tetrahedron: Asymmetry, vol. 2, No. 10, 1991, 1021-1030.
Quast et al., "Synthese von 3,5,5-Trialkyl-3,5-dihydro-4H-1.2.3-triazol-4-onen.sup.2)," Liebigs Ann. Chem. 1986, 1891-1899.
Yamaguchi et al., "A Direct Synthesis of J. Org. Chem. 50, 1985, 1975-1977.
Meyers et al., "Conformational Effects on the Regiochemical Metalation of C.sub.5 -C.sub.13 N-Benzyllactams," J. Am. Chem. Soc. 109, 1987, 4405-4407.
Swinyard et al., "Experimental Detection, Quantification, and Evaluation of Anticonvulsants," Antiepileptic Drugs, Woodbury, Pentry and Pippenger, eds., Raven Press, NY 1982, 111-126.
Lister, R.G., "The use of a plus-maze to measure anxiety in the mouse," Psychopharm. 92:180-185, 1987.
Hamill et al., "Improved Patch-Clamp Techniques for High-Resolution Current Recording from Cells and Cell-Free Membrane Patches," Pflugers Arch. 391:85-100, 1981.
Porter et al., "Antiepileptic Drugs," Chapt. 23, Springer, Berlin, 331-349.
Trevor et al., "Sedative-Hypnotics," Chapt. 21, 306-319.
Loscher at al., "Strategies in antiepileptic drug development: is rational drug design superior to random screening and structural variation?" Epilepsy Research, 17, 1994, 95-134.

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