Hydroxybenzoate salts of metanicotine compounds

Details Hydroxybenzoate salts of metanicotine compounds Hydroxybenzoate salts of metanicotine compounds

2005-11-09

2008-12-02

Seaman, D. Margaret (Department: 1625)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C546S300000

Reexamination Certificate

active

07459469

ABSTRACT:
Patients susceptible to or suffering from conditions and disorders, such as central nervous system disorders, are treated by administering to a patient in need thereof compositions that are hydroxybenzoate salts of E-metanicotine-type compounds. The formation of hydroxybenzoate salts of the E-metanicotine compounds is also useful in purifying the E-metanicotine compounds, as the hydroxybenzoate salts tend to crystallize out, leaving impurities such as Z-metanicotine compounds, and compounds where the double bond has migrated, in solution. If desired, the hydroxybenzoate salts can be converted to either the free base (the E-metanicotine) or to another pharmaceutically acceptable salt form.

REFERENCES:
patent: 4192946 (1980-03-01), Clauson-Kaas et al.
patent: 4487607 (1984-12-01), Rose et al.
patent: 4582823 (1986-04-01), Heffner et al.
patent: 4922901 (1990-05-01), Brooks et al.
patent: 5187166 (1993-02-01), Kikuchi et al.
patent: 5212188 (1993-05-01), Caldwell et al.
patent: 5583140 (1996-12-01), Bencherif et al.
patent: 5597919 (1997-01-01), Dull et al.
patent: 5604231 (1997-02-01), Smith
patent: 5616707 (1997-04-01), Crooks 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: 5726316 (1998-03-01), Crooks
patent: 5811442 (1998-09-01), Ben et al.
patent: 5852041 (1998-12-01), Cosford et al.
patent: 5861423 (1999-01-01), Caldwell
patent: 6232316 (2001-05-01), Dull et al.
patent: 6337351 (2002-01-01), Dull et al.
patent: 6432954 (2002-08-01), Dull et al.
patent: 6492399 (2002-12-01), Dull et al.
patent: 6599897 (2003-07-01), Brown
patent: 6603011 (2003-08-01), Caldwell et al.
patent: 6632823 (2003-10-01), Vernier et al.
patent: 6743812 (2004-06-01), Dull
patent: 6958399 (2005-10-01), Caldwell et al.
patent: 2002/0016460 (2002-02-01), Snow et al.
patent: 2002/0052497 (2002-05-01), Caldwell et al.
patent: 2003/0069272 (2003-04-01), Yerxa et al.
patent: 2004/0044023 (2004-03-01), Cantillon et al.
patent: 2004/0067974 (2004-04-01), Czollner et al.
patent: 2005/0203130 (2005-09-01), Buntinx
patent: 2006/0122238 (2006-06-01), Dull et al.
patent: 2006/0159768 (2006-07-01), Brown
patent: 2007/0265314 (2007-11-01), Dull et al.
patent: 2008/0085888 (2008-04-01), Breining et al.
patent: 0 297 858 (1989-01-01), None
patent: 0 516 409 (1992-12-01), None
patent: 2 295 387 (1996-05-01), None
patent: WO 92/12122 (1992-07-01), 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 97/40011 (1997-10-01), None
patent: WO 99/21834 (1999-05-01), None
patent: WO 99/65876 (1999-12-01), None
patent: WO 00/07600 (2000-02-01), None
patent: 0045846 (2000-08-01), None
patent: WO 01/17943 (2001-03-01), None
patent: 0205801 (2002-01-01), None
patent: 2004031151 (2004-04-01), None
patent: 2005063296 (2005-07-01), None
patent: 2005072742 (2005-08-01), None
patent: 2006053039 (2006-05-01), None
Grottick et al., Behavioural Brain Research, 2000, vol. 117, pp. 197-208.
JP 70012732 B, Daiichi Seiyaku Co.
Acheson, R.M., et al., “Transformations involving the Pyrrolidine Ring of Nicotine,”J. Chem. Soc., 1: 579-585 (1980).
Arneric, S., et al., “Cholinergic channel modulators as a novel therapeutic strategy for Alzheimer's disease,”Exp. Opin. Invest. Drugs, 5(1): 79-100 (1996).
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).
Ashimori, A., et al., “Novel 1,4-Dihydropyridine Calcium Antagonists. I. Synthesis and Hypotensive Activity of 4-(Substituted Pyridyl)-1,4-dihydropyridine Derivatives,”Chem. Pharm. Bull., 38(9): 2446-2458 (1990).
Bannon, A.W., et al., “Broad-Spectrum, Non-Opioid Analgesic Activity by Selective Modulation of Neuronal Nicotinic Acetylcholine Receptors,”Science, 279: 77-81 (1998).
Batkowski, T.,Rocz. Chem., 41: 729-741 (1976).
Bencherif, M., and J.D. Schmitt, “Targeting Neuronal Nicotinic Receptors: A Path to New Therapies,”Current Drug Targets, 1(4): 349-357 (2002).
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).
Borch, R.F., “Reductive Amination with Sodium Cyanoborohydride: N, N-Dimethylcyclohexyl,”Org. Syn., 52: 124-127 (1974).
Brioni, J.D., et al., “The Pharmacology of (—)-Nicotine and Novel Cholinergic Channel Modulators,”Adv. Pharmacol., 37: 153-214 (1997).
Cai, S.X., et al., “5-(N-Oxyaza)-7-substituted-1,4-dihydroquinoxaline-2,3-diones: Novel, Systemically Active and Broad Spectrum Antagonists for NMDA/glycine, AMPA, and Kainate Receptors,”J. Med. Chem., 40(22): 3679-3686 (1997).
Cheng, Y.C., and W.H. Prusoff, “Relationship Between the Inhibition Constant (KI) 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).
Comins, D.L., and M.O. Killpack, “Lithiation of Methoxypyridines Directed by α-Amino Alkoxides,”J. Org. Chem. , 55(1): 69-73 (1990).
Dallacker, F., et al.,Z. Naturforsch., 34b: 1729-1736 (1979).
Damaj, 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).
Dubey, P.R., and C.V. Ratnam, “Synthesis & Spectra of 2-Alkyl—& 6-Bromo-2-alkyl-1H-imidazo[b]pyridines,”Indian J. Chem., 16B(6): 531-533 (1978).
Dwoskin, L.P., et al., “Recent developments in neuronal nicotinic acetylcholine receptor antagonists,”Exp. Opin. Ther. Patents, 10(10): 1561-1581 (2000).
Frank, W.C., et al., “Palladium-Catalyzed Vinylic Substitution Reactions with Heterocyclic Bromides,”J. Org. Chem., 43(15): 2947-2949 (1978).
Frissen, A.E., et al., “Ring-Transformations of Pyrimidines by Intramolecular Diels-Alder Reactions. Synthesis of Annelated Pyridines,”Tetrahedron, 45(3): 803-812 (1989).
Gibson, S., et al., “Principle Components Describing Biological Activities and Molecular Diversity of Heterocyclic Aromatic Ring Fragments,”J. Med. Chem., 39: 4065-4072 (1996).
Greco, C.V., and I.M. Hunsberger, “Synthesis of Some Substituted Pyridylsydnones,”J. Heterocyclic Chem., 7: 761-766 (1970).
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).
Harsing, L.G., Jr., et al., “Dopamine Efflux from Striatum After Chronic Nicotine: Evidence for Autoreceptor Desensitization,”J. Neurochem., 59(1): 48-54 (1992).
Hayes, R.N., et al., “Elimination of Dihydrogen from Collision-activated Alkoxide Negative Ions in the Gas Phase. An Ab initio and Isotope Effect Study,”J. Chem. Soc. Commun., 21: 1431-1432 (1984).
Hery, F., et al., “Control of the Release of Newly Synthetized3H-5-Hydroxytryptamine by Nicotinic and Muscarinic Receptors in Rat Hypothalamic Slices,”Naunyn-Schmiedeberg's Arch. Pharmacol., 296: 91-97 (1977).
Holladay, M. W., et al., “Neuronal Nicotinic Acetylcholine Receptors as Targets for Drug Discovery,”J. Med. Chem., 40(26): 4169-4194 (1997).
Hoyer, D., and H.W.G.M. Boddeke, “Partial agon

Affiliated with

Also associated with

Rating

Hydroxybenzoate salts of metanicotine compounds does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Hydroxybenzoate salts of metanicotine compounds, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Hydroxybenzoate salts of metanicotine compounds will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-4039882