Organic compounds -- part of the class 532-570 series – Organic compounds – Four or more ring nitrogens in the bicyclo ring system
Reexamination Certificate
2006-06-01
2009-06-30
Anderson, Rebecca L (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Four or more ring nitrogens in the bicyclo ring system
C546S329000, C548S122000, C548S123000, C548S124000, C548S125000, C548S206000, C548S215000
Reexamination Certificate
active
07553964
ABSTRACT:
Compounds of formula (I)are useful in treating conditions or disorders prevented by or ameliorated by histamine-3 receptor ligands. Also disclosed are pharmaceutical compositions comprising the histamine-3 receptor ligands, methods for using such compounds and compositions, and a process for preparing compounds within the scope of formula (I).
REFERENCES:
patent: 6515013 (2003-02-01), Bennani et al.
patent: 6620839 (2003-09-01), Bennani et al.
patent: 2005/0171181 (2005-08-01), Wager et al.
patent: 2008/0021081 (2008-01-01), Liu et al.
patent: 0259977 (1987-08-01), None
patent: 94/15928 (1994-07-01), None
patent: 95/20588 (1995-03-01), None
patent: 00/44728 (2000-08-01), None
patent: 02/074758 (2002-09-01), None
patent: 2004/043458 (2004-05-01), None
patent: 2005/080361 (2005-09-01), None
Prodrug [online], [retrieved on Mar. 26, 2007]. Retrieved from the internet, URL; http://en.wikipedia.org/wiki/Prodrug>.
FDA mulls drug to slow late-stage Alzheimer's [online], [retrieved on Sep. 23, 2003]. Retrieved from the Internet, URL; http://www.cnn.com/2003/HEALTH/conditions/09/24/alzheimers.drug.ap/indexhtml>.
Cecil Textbook of Medicine, 20thedition (1996), vol. 2, pp. 1992-1996.
Cecil Textbook of Medicine, 20thedition (1996), vol. 2, pp. 2050-2057.
Arrang, J.-M., et al., “Auto-inhibition of brain histamine releas mediated by a novel class (H3) of histamine receptor”,Nature, 302:832-837 (1983).
Arrang, J.-M., et al., “Highly potent and selective ligands for histamine H3-receptors”,Nature, 327:117-123 (1987).
Barbier, A.J., et al., “Acute wake-promoting actions of JNJ-5207852, a novel, diamine-based H3antagonist”,Br. J. of Pharm., 143:649-661 (2004).
Bernaerts, P., et al., “Histamine H3 antagonist thioperamide dose-dependently enhances memory consolidation and reverse amnesia induced by dizocilpine or scopolamine in a one-trail inhibitory avoidance task in mice”,Beh. Brain Res., 154:211-219 (2004).
Bjenning, C., et al., “Peripherally adminstered Ciproxifan elevates Hypothalamic Histamine Levels and Potently Reduces Food intake in the Sprague Dawley rat”,Hist. Res. In the New Millenium, 499-452 (2001).
Bomann, M.D., et al., “A Mild, Pyridine-Borane-Based Reductive Amination Protocol”,J. Org. Chem., 60:5995-5996 (1995).
Brady, W.T. & Waters, O.H., “Halogenated Ketenes. V. Cycloadditions of Dichloroketene to Olefins”,J. Org. Chem., 32:3703-3705 (1967).
Browman, K.E., et al., “Enhancement of prepulse inhibition of startle in mice by the H3receptor antagonists thioperamide and ciproxifan”,Beh. Brain Res., 153:69-76 (2004).
Chen, Z., “Effects of histamine on MK-801-induced memory deficits in radial maze performance in rats”,Brain Res., 839:186-178 (1999).
Chen, Z., et al., “Pharmacological effects of carcinine on histaminergic neurons in the brain”,Br. J. of Pharm., 143:573-780 (2004).
Clapham, J. & Kilpatrick, G.J., “Thioperamide, the selective histamine H3receptor antagonist, attenuates stimulant-induced locomotor activity in the mouse”,Eur. J. of Pharm., 259:107-114 (1994).
Cowart, M., et al., “4-(2-[2-(2® -Methylpyrrolidin-1-yl)ethyl]benzofuran-5-yl)benzonitrile and Relate 2-Aminoethylbenzofuran H3receptor Antagonist Potently Enhance Cognition and Attention”,J. Med. Chem., 48:38-55 (2005).
De Almeda, M.A.M.R. & Izquierdo, I., “Memory Facilitation by Histamine”,Arch. Int. Pharmacodyn., 283:19-198 (1986).
Dehmlow, E.V. & Büker, S., “Stereoselektive Synthese von 3-substituierten Cyclobutanolen und Folgeprodukten”,Chemische Berichte, 126:2759-2763 (1993).
Delaunois, A., et al., “Modulation of acetylcholine, capsaicin and substance P effects by histamine H3receptors in isolated perfused rabit lungs”,Eur. J. of Pharma., 277:243-250 (1995).
Dimitriadou, V., et al., “Functional relationship between mast cells and C-sensitive nerve fibres evidenced by histamine H3-receptor modulation in a rat lung and spleen”,Clin. Sci., 87:151-163 (1994).
Duméry & Blozovski, D., “Development of amygdaloid cholinergic mediation of passive avoidance learning in the rat”,Exp. Brain Res., 67:61-69 (1987).
Dvorak, C.A., et al., 4-Phenoxypiperidines: Potent, Conformationally Restricted, Non-Imidazole Histamine H3Antagonists,J. Med. Chem., 48:2229-2238 (2005).
Esbenshade, T.A., et al., “Pharmacological and Behavioral properties of A-349821, a selective and potent human histamine H3receptor antagonist”,Biochem. Pharm., 68:933-945 (2004).
Falmagne, J.-B., “Cyclobutanone and cyclobutenone Derivative by Reaction of Tertiary Amides with Alkenes or Alkynes”,Angew. Chem. Int. Ed. Engl., 20(10):879-880 (1981).
Fitzsimons C., et al., “Histamine receptors signaling in epiderman tumor cell lines with H-rasgene alterations”,Inflamm. Res., 747(Supl 1):S50-S51 (1998).
Fox, G.B., et al., “Effects of histamine H3receptor ligands GT-2331 and ciproxifan in a repeated acquisition avoidance response in the spontaneously hypertensive rat pup”,Beh. Brain Res., 131:151-161 (2002).
Fox, G.B., et al., “Two Novel and Selective Nonimidazole H3Receptor Antagonists A-304121 and LA-317920: II. In Vivo Behavioral and Nuerophysiological characterization”,J. of Pharm. &Exp. Ther., a305(30:897-908 (2003).
Fox, G.B., et al., Identification of novel H3receptor (H3R)antagonists with cognition enhancing properties in rats:,Inflamm. Res., 52(Suppl. 1):S31-S32 (2003).
Fox, G.B., et al., “Pharmacological Properties of ABT-239 [4-(2-{2-[(2R)-2-Methylpyrrolidinty]lethal}-benzofuran-5-yl)benzonitrile]: II Neurophysiological Characterization and Broad Preclinical Efficacy in Cognition and Schizophrenia of a Potent and Selective Histamine H3Receptor Antagonists”,J. of Pharm.&Exp. Ther., 313(1):176-190 (2005).
Furniss, B.S., et al., “Vogel's Textbook of Practical Organic Chemistry”, 5thEd.:Table of Contents (1989).
Ghosez, L., et al., “Intramolecular Cycloadditions of Keteniminium Salts. A Novel Apporach Toward Prostaglandins”,Tetrahedron Ltrs., 27(43):5211-5214 (1986).
Glase, S.A., et al., “Chapter 2. Attention Deficit Hyperactivity Disorder: Pathophysiology and Design of New Treatments”,Ann. Rep. In Medic. Chem., 37:11-20 (2002).
Halpern, M.T., “GT-2331 Gliatech, Inc.”,Curr. Opin. In CPNS Invest. Drugs, 1(4):524-527 (1999).
Hancock, A. A., et al “Antiobesity effects of A-331440, an novel non-imidazole histamine H3receptor Antagonist”,Eur. J. of harm., 487:183-197 (2004).
Hancock, A.A., et al., “Histamine H3antagonists in models of obesity”,Inflamm. Res., 53(Suppl. 1):S47-S48 (2004).
Harada, C., et al., “Inhibitory effect of iodophenpropit, a selective histamine H3antagonist, on amygdaloid kindled seizures”,Brain Res. Bull., 63:143-146 (2004).
Houge, C., et al., “Models for Asymmetric [2+2] Cycloadditions”,J. Am. Chem. Soc., 104:2920-2921 (1982).
Hriscu, A., et al., “Evaluarea Experimentala a Eficacitatii Analgezice a Unor Antihistaminice, Ca Dovada a Implicarii receptorilor Histaminergici in Patogenia Dureprii”,Farmacia, XLIX(2):23-30 & 76 (2001).
Huang, Y .-W., et al., “Effect of the histamine H3-antagonist clobenpropit on spatial memory deficits induced by MK-801 as evaluated by radial maze in Sprague-Dawley rats”,Beh. Brain Res., 151:287-293 (2004).
Itoh, E., et al., “Thioperamide, a Histamine H3Receptor Antagonist, Powerfully Suppresses Peptide YY-Induced Food Intake in Rats”,Biol. Psychiatry, 45:475-481 (1999).
“Rules for the Nomenclature of Organic Chemistry”,IUPAC Commission on Nomenclature of Org. Chem., Section E:13-30 (1974).
Kamei, C., et al., “Influence of certain H1-blockers on the step-through active avoidance response in rats”,Psychopharmacology, 102:312-318 (1990).
Kamei, C. & Tasaka
Cowart Marlon D.
Hancock, legal representative Kathryn J.
Liu Huaqing
Abbott Laboratories
Anderson Rebecca L
Chen Portia
Young Shawquia
LandOfFree
Cyclobutyl amine derivatives does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Cyclobutyl amine derivatives, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Cyclobutyl amine derivatives will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-4089485