Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2011-04-05
2011-04-05
Chu, Yong (Department: 1626)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S394000, C548S309700, C548S306100, C546S199000
Reexamination Certificate
active
07919510
ABSTRACT:
The present invention relates to benzimidazole compounds having dual nitric oxide synthase (NOS) inhibitory activity and agonist activity at the mu-opioid receptor, to pharmaceutical and diagnostic compositions containing them, and to their medical use, particularly as compounds for the treatment or prevention of chronic pain, acute pain, migraine, and neuropathic pain.
REFERENCES:
patent: 2935514 (1960-05-01), Hoffmann et al.
patent: 7674809 (2010-03-01), Makovec et al.
patent: 2003/0144286 (2003-07-01), Frenkel et al.
patent: 2003/0212070 (2003-11-01), Schwink et al.
patent: 2007/0112038 (2007-05-01), Marlow et al.
patent: 2009/0048112 (2009-02-01), Elliott et al.
patent: 2009/0099019 (2009-04-01), Dietz et al.
patent: 123466 (1976-12-01), None
patent: 0262873 (1988-04-01), None
patent: 1 388 341 (2004-02-01), None
patent: 1571142 (2005-09-01), None
patent: 10-265450 (1998-10-01), None
patent: WO 95/03298 (1995-02-01), None
patent: WO 95/16685 (1995-06-01), None
patent: WO 03/015769 (2003-02-01), None
Wermuth, C. G.(The Practice of Medicinal Chemistry: Molecular Variations based on Isosteric Replacement, Academic Press, Oxford (1996), pp. 204-237).
Wolff, Manfred E. “Burger's Medicinal Chemistry, 5ed, Part I”, John Wiley & Sons, 1995, pp. 975-977.
Banker et al, “Modern Pharmaceutics, 3ed.”, Marcel Dekker, New York, 1996, pp. 451 and 596.
Anderson et al., “Palladium-Catalyzed Amination of Aryl Nonaflates,”J.Org.Chem,. 68: 9563-9573, 2003.
Antilla et al., “Copper-Catalyzed Coupling of Arylboronic Acids and Amines,”Organic Letters, 3: 2077-2079, 2001.
Ayhan Kilcigil et al., “Synthesis and Antifungal Properties of Some Benzimidazole Derivatives,”Turk. J. Chem., 30: 223-228, 2006.
Baati et al., “An Improved Method for the Preparation of Amidines Via Thiophenylimidic Esters,”Synthesis, 6: 927-929, 1999.
Boev et al., “Synthesis and Antimicrobial Activity of 5(6)-Isothiocyanatobenzazoles,”Khimiko farmatsevticheskii Zhurnal, 24: 40-44, 1990 (translation).
Borowicz et al., “7-Nitroindazole Differentially Affects the Anticonvulsant Activity of Antiepileptic Drugs Against Amygdala-Kindled Seizures in Rats,”Epilepsia, 41: 1112-1118, 2000.
Carroll et al., “Etonitazine. An Improved Synthesis,”J. Med. Chem., 18: 318-320, 1975.
Castro et al., “Enhancement of Oral Absorption in Selective 5-HT1DReceptor Agonists: Fluorinated 3-[3-(Piperidin-1-yl)propyl]indoles,”J. Med. Chem., 41: 2667-2670, 1998.
Collins et al., “N-Phenylamidines as Selective Inhibitors of Human Neuronal Nitric Oxide Synthase: Structure-Activity Studies and Demonstration of in Vivo Activity,”J. Med. Chem., 41: 2858-2871, 1998.
Hobbs et al., “Inhibition of Nitric Oxide Synthase as a Potential Therapeutic Target,”Ann. Rev. Pharmacol. Toxico., 39: 191-220, 1999.
Huang et al., “New Ammonia Equivalents for the Pd-Catalyzed Amination of Aryl Halides,”Org. Lett., 3: 3417-3419, 2001.
Hunger et al., “Benzimidazol-Derivate and Verwandte Heterocyclen III1) Synthese von 1-Aminoalkyl-2-Benzyl-Nitro-Benzimidazolen,”Helv. Chim. Acta., 43:1032-1046, 1960 (English abstract included).
Ito et al., “Inhibition of Neuronal Nitric Oxide Synthase Ameliorates Renal Hyperfiltration in Streptozotocin-Induced Diabetic Rat,”J. Lab Clin. Med., 138: 177-185, 2001.
Kiss et al., “Inhibition of Neuronal Nitric Oxide Synthase Potentiates the Dimethylphenylpiperazinium-Evoked Carrier-Mediated Release of Noradrenaline from Rat Hippocampal Slices,”Neuroscience Lett., 215: 115-118, 1996.
McKay, “The Preparation of N-Substituted-N1-Nitroguanidines by the Reaction of Primary Amines with N-Alkyl-N-Nitroso-N1- Nitroguanidines1,”J. Am. Chem. Soc., 71: 1968-1970, 1949.
Schneller et al., “Synthesis ofproximal-Benzoguanine and a Simplified Synthesis ofproximal-Benzohypoxanthine,”J. Org. Chem., 51: 4067-4070, 1986.
Shearer et al., “S-2-Naphthylmethyl Thioacetimidate Hydrobromide: A New Odorless Reagent For The Mild Synthesis of Substituted Acetamidines,”Tetrahedron Letters, 38: 179-182, 1997.
Shin, “Increased Expression of Neuronal Nitric Oxide Synthase in Astrocytes and Macrophages in the Spinal Cord of Lewis Rats with Autoimmune Encephalomyelitis,”J. Vet. Sci., 2: 195-9, 2001.
Sigmon et al., “Influence of Nitric Oxide Derived From Neuronal Nitric Oxide Synthase on Glomerular Filtration,”Gen. Pharmacol., 34: 95-100, 2000.
Thomas et al., “Rapid In-Plate Generation of Benzimidazole Libraries and Amide Formation Using EEDQ,”Tetrahedron Letters, 38: 5099-5102, 1997.
Wagner et al., “Tuberkulostatisch wirksame N, N'-Diarylthioharnstoffe,”Arzneimittel-Forschung, 19: 719-730, 1969.
Wang et al., “μ Opiate Receptor: cDNA Cloning and Expression,”Proc.Natl.Acad.Sci USA, 90: 10230-10234, 1993.
Wang et al., “Human μ Opiate Receptor: cDNA and Genomic Clones, Pharmacologic Characterization and Chromosomal Assignment,”FEBS Lett., 338: 217-222, 1994.
Willitzer et al., “Synthese and Antivirale Wirksamkeit von Substituierten 5-Ureido-und-5-Thioureidobenzimidazolderivaten,”Pharmazie33: 30-38, 1978.
Wolfe et al., “Simple, Efficient Catalyst System for the Palladium-Catalyzed Amination of Aryl Chlorides, Bromides, and Triflates,”J. Org. Chem., 65: 1158-1174, 2000.
International Preliminary Report on Patentability, (PCT/IB2006/003075), issued Nov. 20, 2007.
International Search Report, (PCT/IB2006/003075), mailed Mar. 27, 2007.
Written Opinion of the International Searching Authority, (PCT/IB2006/003075), mailed Mar. 27, 2007.
Extended European Search Report for EP Application No. 06809164.4-2101 dated Jul. 15, 2009.
Andrews John
Maddaford Shawn
Rakhit Suman
Renton Paul
Chu Yong
Clark & Elbing LLP
NeurAxon, Inc
Rodriguez-Garcia Valerie
LandOfFree
Substituted benzimidazole compounds with dual NOS inhibitory... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Substituted benzimidazole compounds with dual NOS inhibitory..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Substituted benzimidazole compounds with dual NOS inhibitory... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2622818