Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1995-06-07
1998-01-06
Davis, Zinna Northington
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
5462784, 5462791, C07D40104, A61K 3144
Patent
active
057055122
ABSTRACT:
The present invention provides a class of pyridine compounds which are modulators of acetylcholine receptors, i.e., compounds which displace acetylcholine receptor ligands from their binding sites. Invention compounds may act as agonists, partial agonists, antagonists or allosteric modulators of acetylcholine receptors, and are useful for a variety of therapeutic applications, such as the treatment of Alzheimer's disease and other disorders involving memory loss and/or dementia; disorders of attention and focus; disorders of extrapyramidal motor function; mood and emotional disorders; substance abuse including withdrawal syndromes and substitution therapy; neuroendocrine disorders and dysregulation of food intake, including bulimia and anorexia; disorders of nociception and control of pain; autonomic disorders including dysfunction of gastrointestinal motility and function; pheochromocytoma; cardiovascular dysfunction including hypertension and cardia arrhythmias, comedication in surgical procedures, and the like.
REFERENCES:
patent: 3247213 (1966-04-01), Buchel et al.
patent: 4155909 (1979-05-01), Sanders et al.
patent: 4321387 (1982-03-01), Chavdarian et al.
patent: 4965074 (1990-10-01), Leeson
patent: 5248690 (1993-09-01), Caldwel et al.
patent: 5278176 (1994-01-01), Lin
patent: 5399575 (1995-03-01), Friebe et al.
patent: 5418229 (1995-05-01), Alker et al.
Aislaitner et al., "The Synthesis of 1'-Methyl-2'-Oxoanabasine, An Analogue Of Cotinine" Bioorganic Med. Chem. Lett. 4:515-520 (1994).
Albanese et al., "Chronic Administration of 1-Methyl-4-Phenyl-1,2,3,6-Tetrahydropyridine To Monkeys: Behavioural, Morphological And Biochemical Correlates" Neuroscience 55:823-832 (1993).
Alkondon and Albuquerque, "Diversity of Nicotinic Acetylcholine Receptors in Rat Hippocampal Neurons. III. Agonist Actions of the Novel Alkaloid Epibatidine and Analysis of Type II Current" J. Pharmacol. Exper. Therap. 274:771-782 (1995). Cholinergic Channel Ligand" J. Pharmacol. Exper. Therap. 273:1434-1441 (1995).
Arneric, Stephen P., "New Nicotinic Agonists And Cerebral Blood Flow" Abbott Laboratories, Neuroscience 386-394, 1991.
Aubert et al., "Comparative Alterations of Nicotinic and Muscarinic Binding Sites in Alzheimer's and Parkinson's Diseases" J. Neurochem. 58:529-541 (1992).
Brioni et al., "Nicotinic receptor agonists exhibit anxiolytic-like effects on the elevated plus-maze test" Eur J. Pharmacol. 238:1-8 (1993).
Burk et al., "Catalytic Asymmetric Reductive Amination of Ketones via Highly Enantioselective Hydrogenation of the C=N Double Bond" Tetrahedron 50:4399-4428 (1994).
Burk et al., "Preparation and Use of C.sub.2 -Symmetric Bis(phospholanes): Production of .alpha.-Amino Acid Derivatives via Highly Enantioselective Hydrogenation Reactions" J. Am. Chem. Soc. 115:10125 (1993).
Chaki et al., "Design and Syntheses of 4-Acylaminopyridine Derivatives: Novel High Affinity Choline Uptake Enhancers I.sup.1 " Bioorgan. & Med. Chem. Let. 5:1489-1494 (1995).
Chavdarian et al., "Synthesis of Optically Active Nicotinoids" J. Org. Chem. 47:1069-1073 (1982).
Cho and Chun, "Asymmetric Reduction of N-Substituted Ketimines with the Reagent prepared from Borane and (S)-(-)-2-Amino-3-methyl-1, 1-diphenylbutan-1-ol (Itsuno's Reagent) : Enantioselective Synthesis of Optically Active Secondary Amines" Chem. Soc. Perk. 1:3200-3201 (1990).
Christensen et al., "On the Supersensitivity of Dopamine Receptors, Induced by Neuroleptics" Psychoparmacol. 48:1-6 (1976).
Clow et al., "Changes In Dopamine-Mediated Behaviour During One Year's Neuroliptic Administration" Euro. J. Pharmacol. 57:365-375 (1979).
Coyle et al., "Kainic Acid: Insights From a Neurotoxin into the Pathophysiology of Huntington's Disease" Neurobehav. Toxicol. Tetatol. 5:617-624 (1983).
Cushman and Castagnoli, Jr., "The Synthesis of trans-3'-Methylnicotine" J. Org. Chem. 37:1268-1271 (1972).
D'Amour and Smith, "A Method For Determining Loss Of Pain Sensation" J. Pharmacol. Exp. Ther. 72:74-79 (1941).
De Fiebre et al., "Characterization of a Series of Anabaseine-Derived Compounds Reveals That the 3-(4)-Dimethylaminocinnamylidine Derivative Is a Selective Agonist at Neuronal Nicotinic .alpha.7/.sup.125 .vertline.-.alpha.-Bungarotoxin Receptor Subtypes" Mol. Pharmacol. 47:164-171 (1995). Slices By Quaternary N-Methylated Nicotine Metabolites" Life Sciences 50:PL-233 -PL-237 (1992).
Emerich et al., "Nicotine Potentiates Haloperidol-Induced Catalepsy and Locomotor Hypoactivity" Pharmacol. Biochem. Behav. 38:875-880 (1991).
Estrella et al., "A further study of the neuromuscular effects of vesamicol (AH5183) and of its enantiomer specificity" Br. J. Pharmacol. 93:759-768 (1988). Cerebral Cortex: Comparison Between Alzheimer's Disease and the Normal" J. Neurochem. 47:1948 (1986).
Haglid, F., "The Methylation of Nicotine with Methyl-lithium" Acta Chem. Scand. 21:329-334 (1967).
Hansson et al., "On the Quantitative Structure--Activity Relationships of Meta -Substituted (S)-Phenylpiperidines, a Class of Preferential Dopamine D.sub.2 Autoreceptor Ligands: Modeling of Dopamine Synthesis and Release in Vivo by Means of Partial Least Spuares Regression" J. Med. Chem. 38:3121-3131 (1995).
Hwang et al., "A Synthesis of .alpha.-Substituted Amines" J. Org. Chem. 50:3885-3890 (1985).
Iwamoto, Edgar T., "Antinociception after Nicotine Administration into the Mesopontine Tegmentum of Rats: Evidence for Muscarinic Actions.sup.1 " J. Pharmacol. Exp. Ther. 251:412-421 (1989).
Janson et al., "Differential effects of acute and chronic nicotine treatment of MPTP-(1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine) induced degeneration of nigrostriatal dopamine neurons in the black mouse" Clin. Investig. 70:232-238 (1992).
Jacob III, Peyton, "Resolution of (.+-.)-5-Bromonornicotine. Synthesis of ( S )-Nornicotine of High Enantiomeric Purity" J. Org. Chem. 47:4165-4167 (1982).
Kashiwabara et al., "Comparative Vasodepressor Effects of 3-Pyridine Derivatives Possessing the Cyanoamidine or Amide Structure in Pithed Rats" Arch. int. Pharmacodyn 328:297-306 (1994).
Kawate et al., "Asymmetric Reduction of Imines with Chiral Dialkoxyboranes" Tetrahedron Asym. 3:227-230 (1992).
Kitamura et al., "General Asymmetric Synthesis of Isoquinoline Alkaloids. Enantioselective Hydrogenation of Enamides Catalyzed by BINAP-Ruthenium(II) Complexes" J. Org. Chem. 59:297-310 (1994).
Klockgether and Turski, "NMDA Antagonists Potentiate Antiparkinsonian Actions of .sub.L -Dopa in Monoamine-depleted Rats" Ann. Neurol. 28:539-546 (1990).
Lange et al., "Altered Muscarinic and Nicotinic Receptor Densities in Cortical and Subcortical Brain Regions in Parkinson's Disease" J. Neurochem. 60:197-203 (1993).
Leete et al., "Formation Of 5-Fluoronicotine From 5-Fluoronicotinic Acid In Nicotiana Tabacum" Phytochem. 10:2687-2692 (1971).
Lin et al., "Synthesis and Evaluation of Nicotine Analogs as Neuronal Nicotinic Acetylcholine Receptor Ligands" J. Med. Chem. 37:3542-3553.
Manescalchi et al., "Reductive Amination of 1,4-and 1,5-Dicarbonyl Compounds with (S)-Valine Methyl Ester. Synthesis of (S)-2-Phenylpyrrolidine and (S)-2-Phenylpiperidine." Tetrahedron Letters 35:2775-2778 (1994).
Mathre et al., "A Practical Process for the Preparation of Boarane. A Highly Enantioselective Stoichiometric and Catalytic Reducing Agent" J. Org. Chem. 58:2880-2888 (1993).
Miyata et al., "Role of the Serotonin.sub.3 Receptor in Stress-Induced Defection" J. Pharmacol. Exp. Ther. 261:297-303 (1992).
Natsugari et al., "Novel, Potent, and Orally Active Substance P Antagonists: Synthesis and Antagonist Activity of N-Benzylcarboxamide
Nilsson and Hallberg, "Regioselective Palladium-Catalyzed Tandem .alpha.-Arylation/Isomerization of Cyclic Enamides" J. Org. Chem. 55:2464-2470 (1990).
O'Neill et al., "Evidence of an involvement of D1 and D2 dopamine receptors in mediating nicotine-induced hyeractivity in rats" Psychopharmacology 104:343-350 (1991).
Ozawa et al., "Palladium-Catalyzed Asymmetric Alkenylation of Cyclic Olefins" Tetrahedron Letters 34:2505-2508 (1993).
Pellow et al., "Validation of open: closed arm entries in an elevated plus-maze as a mea
Cosford Nicholas D.
Mc Donald Ian A.
Whitten Jeffrey P.
Davis Zinna Northington
Reiter Stephen E.
SIBIA Neurosciences Inc.
LandOfFree
Modulators of acetylcholine receptors does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Modulators of acetylcholine receptors, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Modulators of acetylcholine receptors will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2329405