Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2006-06-12
2008-05-20
Desai, Rita (Department: 1625)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C546S278700
Reexamination Certificate
active
07375110
ABSTRACT:
Compounds, pharmaceutical compositions including the compounds, and methods of preparation and use thereof are disclosed. The compounds are N-aryl diazaspirocyclic compounds, bridged analogs of N-heteroaryl diazaspirocyclic compounds, or prodrugs or metabolites of these compounds. The aryl group can be a five- or six-membered heterocyclic ring (heteroaryl). The compounds and compositions can be used to treat and/or prevent a wide variety of conditions or disorders, particularly those disorders characterized by dysfunction of nicotinic cholinergic neurotransmission, including disorders involving neuromodulation of neurotransmitter release, such as dopamine release. CNS disorders, which are characterized by an alteration in normal neurotransmitter release, are another example of disorders that can be treated and/or prevented. The compounds and compositions can also be used to alleviate pain. The compounds can: (i) alter the number of nicotinic cholinergic receptors of the brain of the patient, (ii) exhibit neuroprotective effects and (iii) when employed in effective amounts, not result in appreciable adverse side effects (e.g., side effects such as significant increases in blood pressure and heart rate, significant negative effects upon the gastro-intestinal tract, and significant effects upon skeletal muscle).
REFERENCES:
patent: 3282947 (1966-11-01), Grogan et al.
patent: 4665079 (1987-05-01), Culbertson et al.
patent: 4922901 (1990-05-01), Brooks et al.
patent: 5187166 (1993-02-01), Kikuchi et al.
patent: 5583140 (1996-12-01), Bencherif et al.
patent: 5597919 (1997-01-01), Dull et al.
patent: 5604231 (1997-02-01), Smith et al.
patent: 5616716 (1997-04-01), Dull et al.
patent: 5663356 (1997-09-01), Ruecroft et al.
patent: 5672601 (1997-09-01), Cignarella
patent: 5733912 (1998-03-01), Wasicak et al.
patent: 5852041 (1998-12-01), Cosford et al.
patent: 6022868 (2000-02-01), Olesen et al.
patent: 2003/0092700 (2003-05-01), Czollner et al.
patent: 2003/0171359 (2003-09-01), Dahmann et al.
patent: 0 297 858 (1989-01-01), None
patent: 0 360 390 (1990-03-01), None
patent: 0 417 631 (1991-03-01), None
patent: 0 970 957 (2000-01-01), None
patent: 2 142 332 (1985-01-01), None
patent: 2 295 387 (1996-05-01), None
patent: WO 94/08992 (1994-04-01), None
patent: WO 96/31475 (1996-10-01), None
patent: WO 96/40682 (1996-12-01), None
patent: WO 97/40049 (1997-10-01), None
patent: WO 98/25619 (1998-06-01), None
patent: WO 99/21834 (1999-05-01), None
patent: WO 01/30780 (2001-05-01), None
patent: WO 01/66546 (2001-09-01), None
Abramovitch, R.A., editor, “Pyridine and Its Derivatives,” Supp. Part Three, pp. 3-5, inChemistry of Heterocyclic Compounds, vol. 14 (Interscience Publishers, 1974).
Adamcik, J.A., and E.J. Miklasiewicz, “Cyanoethylation. I. Weakly Basic Catalysts in the Reaction of Acrylonitrile with Active Methylene Compounds,”J. Org. Chem. 28:336-339 (1963).
Arneric, S., et al., “Preclinical Pharmacology of ABT-418: A Prototypical Cholinergic Channel Activator for the Potential Treatment of Alzheimer's Disease,”CNS Drug Rev., 1(1): 1-26 (1995).
Arneric, S.P., et al., “Cholinergic channel modulators as a novel therapeutic strategy for Alzheimer's disease,”Exp. Opin. Invest. Drugs, 5(1): 79-100 (1996).
Bannon, A.W., et al., “Broad-Spectrum, Non-Opioid Analgesic Activity by Selective Modulation of Neuronal Nicotinic Acetylcholine Receptors,”Science, 279: 77-81 (1998).
Bencherif, M., et al., “RJR-2403: A Nicotinic Agonist with CNS Selectivity I: In Vitro Characterization,”J. Pharmacol. Exper. Therapeutics, 279(3):1413-1421 (1996).
Berkowitz, D.B., and M.K. Smith, “Enantiomerically Enriched α-Methyl Amino Acids. Use of an Acyclic, Chiral Alanine-Derived Dianion with a High Diastereofacial Bias,”J. Org. Chem., 60: 1233-1238 (1995).
Brioni, J.D., et al., “The Pharmacology of (—)-Nicotine and Novel Cholinergic Channel Modulators,”Adv. Pharmacol., 37: 153-215 (1997).
Burger, A., et al., “Some Derivatives of Tetrahydropyran as Potential Pharmacodynamic Agents,”J. Am. Chem. Soc., 72: 5512-5515 (1950).
Cheng, Y., and W.H. Prusoff, “Relationship Between the Inhibition Constant (K1) and the Concentration of Inhibitor which Causes 50 Per Cent inhibition (I50) of an Enzymatic Reaction,”Biochem. Pharmacol. 22(23): 3099-3108 (1973).
Chiari, A., et al., “Sex Differences in Cholinergic Analgesia I: A Supplemental Nicotinic Mechanism in Normal Females,”Anesthesiology, 91(5): 1447-1454 (1999).
Ciblat, S., et al., “A new route to 2-spiropiperidines,”Tet. Lett., 42: 4815-4817 (2001).
Clarke, K., and K. Rothwell, “A Kinetic Study of the Effect of Substituents on the Rate of Formation of Alkylpyridinium Halides in Nitromethane Solution,”J. Chem. Soc., 1885-1895 (1960).
Comins, D.L, and M.O. Killpack, “Lithiation of Methoxypyridines Directed by α-Amino Alkoxides,”J. Org. Chem., 55(1): 69-73 (1990).
Cosford, N.D.P., et al., “(S)-(—) 5- Ethynyl-3-(1-methyl-2-pyrrolidinyl) pyridine Maleate (SIB-1508Y): A Novel Anti-Parkinsonian Agent with Selectivity for Neuronal Nicotinic Acetylcholine Receptors,”J. Med. Chem., 39(17) : 3235-3237 (1996).
Culbertson, T.P., et al., “Quinolone Antibacterial Agents Substituted at the 7-Position with Spiroamines. Synthesis and Structure-Activity Relationships,”J. Med. Chem., 33(8): 2270-2275 (1990).
Damaj, M.I., et al., “Analgesic Activity of Metanicotine, A Selective Nicotinic Agonist,”Society for Neuroscience, 23: 669 Abstract 266.9 (1997).
Damaj, M.I., et al., “Antinociceptive and Pharmacological Effects of Metanicotine, a Selective Nicotinic Agonist,”J. Pharmacol. Exp. Ther., 291(1): 390-398 (1999).
Decina, P., et al., “Cigarette Smoking and Neuroleptic-Induced Parkinsonism,”Biol. Psychiatry, 28(6): 502-508 (1990).
Elliott, J.M., et al., “Serine Derived NK1Antagonists 2: A Pharmacophore Model for Arylsulfonamide Binding,”Bioorg. Med. Chem. Lett., 8: 1851-1856 (1998).
Fornicola, R.S., et al., “A New Synthesis of α-Amino Acid Derivatives Employing Methyl Nitroacetate as a Versatile Glycine Template,”J. Org. Chem., 63(11): 3528-3529 (1998).
Genin, M.J., et al., “Synthesis and Crystal Structure of a Peptidomimetic Containing the (R)-4,4-Spiro Lactam Type-II β-Turn Mimic,”J. Org. Chem., 58(8): 2334-2237 (1993).
Genin, M.J., and R.L. Johnson, “Design, Synthesis, and Conformational Analysis of a Novel Spiro-Bicyclic System as a Type II β-Turn Peptidomimetic,”J. Amer. Chem. Soc., 114(23): 8778-8783 (1992).
Gibson, S., et al., “Principal Components Describing Biological Activities and Molecular Diversity of Heterocyclic Aromatic Ring Fragments,”J. Med. Chem., 39(20): 4065-4072 (1996).
Grogan, C.H., et al. “Spiranes. VII. Neuroleptics Derived from Azaspiranes,”J. Med. Chem., 8: 62-73 (1965).
Hall, G.H., and D.M. Turner, “Effects of Nicotine on the Release of3H-Noradrenaline from the Hypothalamus,”Biochemical Pharmacology, 21: 1829-1838 (1972).
Hamon, M., “Neuropharmacology of anxiety: perspectives and prospects,”TiPS, 15: 36-39 (1994).
Hansch, C., et al., “The Parabolic Dependence of Drug Action upon Lipophilic Character as Revealed by a Study of Hypnotics,”J. Med. Chem., 11(1): 1-11 (1967).
Hansch, C., et al., “A Survey of Hammett Substituent Constants and Resonance and Field Parameters,”Chem. Rev., 91(2): 165-195 (1991).
Hansen, M.M., et al., “An Enantioselective Synthesis of Cis Perhydroisoquinoline LY235959,”J. Org. Chem., 63(3): 775-785 (1998).
Harsing, Jr., L.G., et al., “Dopamine Efflux from Striatum After Chronic Nicotine: Evidence for Autoreceptor Desensitization,”J. Neurochem., 59(1): 48-54 (1992).
Hartwig, J.F., et al., “Room-Temperature Palladium-Catalyzed Amination of Aryl Bromides and Chlorides and Ext
Bhatti Balwinder S.
Miller Craig Harrison
Schmitt Jeffrey Daniel
Desai Rita
Targacept, Inc.
Womble Carlyle Sandridge & Rice PLLC
LandOfFree
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