Cyanoamidine P2X 7 antagonists for the treatment of pain

Details Cyanoamidine P2X 7 antagonists for the treatment of pain Cyanoamidine P2X 7 antagonists for the treatment of pain

2007-07-10

2007-07-10

Shameem, Golam M. M. (Department: 1626)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

C546S112000, C546S152000, C546S174000, C546S175000, C546S329000, C546S334000, C549S029000, C549S074000, C549S076000, C558S303000, C558S388000, C558S390000, C558S392000, C514S438000

Reexamination Certificate

active

10909502

ABSTRACT:
Novel cyanoamidines compounds of formula (I) and (II)and their derivatives wherein R1-R12are as defined in the specification act as antagonists of the P2X7receptor. These compounds are particularly useful in the treatment of pain, inflammation and neurodegeneration states.

REFERENCES:
patent: 5380734 (1995-01-01), Hsu et al.
patent: 2003/0004513 (2003-01-01), Guzman et al.
patent: 2003/0187031 (2003-10-01), Alcaraz et al.
patent: 0 412 531 (1991-02-01), None
patent: 0 934 941 (1999-08-01), None
patent: 04 295473 (1992-10-01), None
patent: 91/04965 (1991-04-01), None
patent: 92/06978 (1992-04-01), None
patent: 93/15055 (1993-08-01), None
patent: 95/31448 (1995-11-01), None
Kiriyama, Kazuhisa, et al., “Insecticidal and neuroblocking activities of acetamiprid and related compounds”, XP002355181, retrieved from STN Database accession No. 2003:341680 abstract.
Kupchik, E.J. and Hanke, H.E., “Reactions of Thioamides with Bis(triphenylstannyl) carbodiimide and (Triphenylstannyl) Cyanamide”, Journal of Organometallic Chemistry, vol. 97, pp. 39-44, 1975.
Mase, Toshiyasu, et al., “Preparation of pyridylpyrrolothiazole derivatives as platelet activating factor (PAF) antagonists”, XP002355182, retrieved from STN Database accession No. 1992:255603 abstract.
Anderson C., et al., “ATP-Activated Glutamate Release through Non-Selective P2Z/P2X7 Like Channels in Cultured Mouse Astrocytes”, Drug Dev. Res., Abstracts from Purines 2000, Sec. 177, vol. 50, pp. 92 (2000).
G. Dell'Antonio, “Antinociceptive effect of a new P2z/P2X7 antagonist, oxidized ATP, in arthritic rats”, Neuroscience Letters 327, pp. 87-90 (2002).
S.M. Berge, et al., “Pharmaceutical Salts”, J. Pharmaceutical Sciences, vol. 66, No. 1, pp. 1-19 (1977).
Bianchi, et al., Pharmacological characterization of recombinant human and rat P2X receptor subtypes , European. Journal of Pharmacol. vol. 376, pp. 127-138 (1999).
Blanchette et al., “The Willgerodt Reaction in the Heterocyclic Series. II. Temperature Studies with Thienyl Ketones”, Journal of Amer. Chem. Soc., vol. 74, p. 1066-1067 (1952).
Brough, D., et al., “Purinergic (P2X7) Receptor Activation of Microglia Induces Cell Death via an Interleukin-1-Independent Mechanism”, Molecular and Cellular Neuroscience, vol. 19, pp. 272-280 (2002).
Collo, G., “Tissue Distribution of the P2X7Receptor”, Neuropharmacology, vol. 36, No. 9, pp. 1277-1283, (1997).
De Tar, et al., “The Willgerodt Reaction. II. A Study of Reaction Conditions with Acetophenone and Other Ketones”, J. Amer. Chem. Soc., vol. 68, pp. 2025-2028 (1946).
Deuchars, Susan, et al., “Neuronal P2X7Receptors are Targeted to Presynaptic Terminals in the Central and Peripheral Nervous Systems”, The Journal of Neuroscience, vol. 21(18), pp. 7143-7152, (Sep. 15, 2001).
Dixon, Ann., “Efficient Analysis of Experimental Observations”, Rev. Pharmacol. Toxicol., vol. 20, pp. 441-462 (1980).
Edwards, M. and Williams, “Catalytic Electronic Activation: Indirect “Wittig” Reaction of Alcohols”, J., Angewandte Chemie, Intl. Edition vol. 41 (24), pp. 4740-4743 (2002).
Engler, T.A., “An improved method for direct conversion of heteroaryl-aldehydes to heteroaryl-acetonitriles”, Tetrahedron Letters, vol. 44 (14), pp. 2903-2905 (2003).
Ganellin, C. Robin, et al., “Synthesis of Potent Non-imidazole Histamine H3-Receptor Antagonists”, Arch. Pharm. Pharm. Med. Chem. , vol. 331, pp. 395-404 (1998).
Hatcher, Jonathan, et al., “Disruption of the P2X7 Purinoceptor Gene Abolishes Chronic Inflammatory and Neuropathic Pain”, (6thIntl. Conf. On the Mechanisms and Treatment of Neuropathic Pain, San Francisco, CA (Sep. 18-20, 2003) GlaxoSmithKline, Dept. of Pain Research, Neurology & Gastroenterology CEDD.
T. Higuchi and V. Stella (Editors), Pro-Drugs as Novel Delivery Systems, V. 14 of the A.C.S. Symposium Series, (1975).
Humphrey BD and Dubyak GR, “Induction of the P2z/P2X7Nucleotide Receptor and Associated Phospholipase D Activity by Lipopolysaccharide and IFN-γ in the Human THP-1 Monocytic Cell Line”, J. Immunology, vol. 157 pp. 5627-5637 (1996).
Jacobson, K.A., et al., “Adenosine and Adenine Nucleotides: From Molecular Biology to Integrative Physiology”, L. Belardinelli and A. Pelleg (eds.) pp. 149-166 (1995).
Kelley, James L., et al., 8-Amino-3-benzyl-1,22,4-triazolo[4,3-a] pyrazines. Synthesis and Anticonvulsant Activity, Journal of Medicinal Chemistry, vol. 38, (18), pp. 3676-3679 (1995).
Kim, Sun Ho and Chung, Jin Mo, “An experimental model for peripheral neuropathy produced by segmental spinal nerve ligation in the rat”, Pain, vol. 50, pp. 355-363 (1992).
Mayer, Joachim M., et al., Structural Factors Affecting the Basicity of w-Pyridylallkanols; w-Pyridylalkanamides and w-Pyridylalkylamines, Helvetica Chimica Acta, vol. 65, pp. 1868-1884 (1982).
Meyer, M.D., et al., Structure-Activity Studies for a Novel Series of N-(Arylethyl)-N(1',2,3,4-tetrahydronaphthalen-1-ylmethyl)-N-methylamines Possessing dual 5-HT Uptake Inhibiting and a2-Antagonistic Activities, Journal of Med. Chem., vol. 40, No. 7, pp. 1049-1062 (1997).
Moehrle, H., et al., Chemical Sciences, vol. 53(11), pp. 1369-1378 (1998).
Perretti M., et al., “Evidence that endogenous interleukin-1 is involved in leukocyte migration in acute experimental infglammation in rats and mice”, Agents Actions, vol. 35 (1-2), pp. 71-78 (1992).
Edward B. Roche, (Editor)., Bioreversible Carriers in Drug Design, American Pharmaceutical Association and Pergamon Press (1987).
Ruechardt, et al., “Die Zerfallsgeschwindigkeit des p-Methylmercapto-phenylperessigsaure-tert.-butylesters”, Chem. Ber., vol. 100, p. 654 (1967).
Sato, Y., et al., “Syntheses of 2-hydroxymethylnicotinic Acid Lactone, 2-Hydroxymethylpyridine-3-acetic Acid Lactone, and Sope of their Derivatives”, Chem. Pharm. Bull., vol. 8, pp. 427-435 (1960).
Torok K., et al., “Measurement and drug induced modulation of interleukin-1 level during zymosan peritonitis in mice”, Inflamm. Res. vol. 44 (6) pp. 248-252 (1995).
Tsatsaronis, G.C., “Synthesis of 4,5-Disubstituted Pyrimidines”, Journal of Org. Chem., vol. 35, No. 2, p. 438-441 (1970).
Verhoef, Philip A., “P2X7 Receptor-Dependent Blebbing and the Activation of Rho-Effector Kinases, Caspases, and IL-1Beta Release1”, The Journal of Immunology, vol. 170, pp. 5728-5738 (2003).
Wagner, G. and Vieweg, H., “Synthese von Amidinochinolinen und Amidinochinolonen-(4)”, Pharmazie, vol. 31, pp. 145-148 (1976).
Wang, X., et al., “P2X7 receptor inhibition improves recovery after spinal cord injury”, Nature Medicine, vol. 10, No. 8, pp. 821-827 (Aug. 2004).
Weintraub, L., et al., “A convenient General Synthesis of Amidines”, J. Org. Chem., vol. 33(4), pp. 1679-1681 (Apr. 1968).

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