Benzimidazole compounds and antiviral uses thereof

The present invention relates to novel benzimidazole compounds that have useful antiviral activity. More specifically, the invention encompasses benzimidazole compounds that inhibit membrane fusion associated events such as viral transmission, reduce viral load or otherwise treat viral infections. T...

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Main Authors Lackey, John William, Kinder, Daniel S, Tvermoes, Nicolai A
Format Patent
LanguageEnglish
Published 18.04.2006
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Abstract The present invention relates to novel benzimidazole compounds that have useful antiviral activity. More specifically, the invention encompasses benzimidazole compounds that inhibit membrane fusion associated events such as viral transmission, reduce viral load or otherwise treat viral infections. The invention also encompasses the use of benzimidazole compounds as inhibitors of membrane fusion associated events, such as viral transmission. In another embodiment, the invention encompasses processes for making benzimidazole compounds, methods of using the benzimidazole compounds and compositions comprising the benzimidazole compounds. Finally, the invention provides methods for treating, preventing or ameliorating symptoms associated with respiratory infection, particularly that caused by Respiratory Syncytial Virus utilizing the novel benzimidazole compounds of the invention.
AbstractList The present invention relates to novel benzimidazole compounds that have useful antiviral activity. More specifically, the invention encompasses benzimidazole compounds that inhibit membrane fusion associated events such as viral transmission, reduce viral load or otherwise treat viral infections. The invention also encompasses the use of benzimidazole compounds as inhibitors of membrane fusion associated events, such as viral transmission. In another embodiment, the invention encompasses processes for making benzimidazole compounds, methods of using the benzimidazole compounds and compositions comprising the benzimidazole compounds. Finally, the invention provides methods for treating, preventing or ameliorating symptoms associated with respiratory infection, particularly that caused by Respiratory Syncytial Virus utilizing the novel benzimidazole compounds of the invention.
Author Tvermoes, Nicolai A
Kinder, Daniel S
Lackey, John William
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References Steck et al., 1948, "Absorption spectra of heterocyclic compounds. III. Some benzimidazole derivatives", J. of the Amer. Chem. Society. 70:3406-3410.
(WO 99/44596) 19990900
(9-3065) 19970700
Abman et al., 1988, "Role of respiratory syncytial virus in early hospitalizations for respiratory distress of young infants with cystic fibrosis", J Pediatr. 113(5):826-30.
Ruuskanen et al., "Respiratory syncytial virus", Curr Probl Pediatr., Feb. 1993; 23(2):50-79.
Collings et al., 1984, "Identification of a tenth mRNA of respiratory syncytial virus and assignment of polypeptides to the 10 viral genes", J Virol. 49(2):572-8.
Saudek et al., 1989, "A preliminary trial of the programmable implantable medication system for insulin delivery", N Engl J Med. 321(9):574-9.
Doud et al., 1992, "Respiratory syncytial virus pneumonia in a lung transplant recipient: case report", J Heart Lung Transplant. 11(1 Pt 1):77-9.
Murphy et al., 1994, "An update on approaches to the development of respiratory syncytial virus (RSV) and parainfluenza virus type 3 (PIV3) vaccines", Virus Res. 32(1):13-36.
Wu and Wu, 1987, "Receptor-mediated in vitro gene transformation by a soluble DNA carrier system", J Biol Chem. 262(10):4429-32.
Wyatt et al., 1995, "Benzophenone Derivatives: A Novel Series of Potent and Selective Inhibitors of Human Immunodeficiency Virus Type I Reverse Transcriptionase", J. Med. Chem. 38:1657-1665.
Johnson et al., 1997, "Development of a humanized monoclonal antibody (MEDI-493) with potent in vitro and in vivo activity against respiratory synctial virus", J Infect Dis. 176(5):1215-24.
Falsey et al., 1991, "Noninfluenza respiratory virus infection in long-term care facilities", Infect Control Hosp Epidemiol. 12(10):602-8.
(WO-97/30991) 19970800
(WO 98/37072) 19980800
Hall CB, 1993, "Respiratory Syntial Virus: What we know now", Contemp Pediatr. 10:92-110.
(WO 01/00615) 20010100
Bobosik et al., Heterocycles (1993), 35(2), pp. 1067-1074.
(WO 01/27090) 20010400
CA Registry No. 152072-73-6, entry date into the Registry file Jan. 4, 1994.
Sinnott et al., 1988, "Respiratory syncytial virus pneumonia in a cardiac transplant recipient", J Infect Dis. 158(3):650-1.
Pringle et al., 1985, "A survey of respiratory syncytial virus and parainfluenza virus type 3 neutralising and immunoprecipitating antibodies in relation to Paget disease", J Med Virol. 17(4):377-86.
Ishida et al., 1975, "Tris (benzimidazo)-1,3,5-triazine from the thermolysis of 2-aryloxybeznzimaidazoles", Bulletin of Chem. Soc. Of Japan 48:956-959.
Carstensen, J., 1995, Drug Stability: Principles and Practice, 2nd ed., Marcel Dekker, NY, NY pp. 379-380.
(WO 93/14088) 19930700
Colacino (5891874) 19990400
Kuzmierkiewicz, CA 106:50163, 1987.
Hollinshead and Smith, "Effects of Certain Purines and Related Compounds on Virus Propagation", Purines in Virus Chemotherapy 123:54-62, 1958.
Prince et al., 1985, "Quantitative aspects of passive immunity of respiratory syncytial virus infection in infant cotton rats", J Virol. Sep.; 55(3):517-20.
Maynard et al. (5932571) 19990800
Whimbey et al., 1995, "Respiratory syncytial virus pneumonia in hospitalized adult patients with leukemia", Clin Infect Dis. 21(2):376-9.
Howard et al., 1989, Intracerebral drug delivery in rats with lesion-induced memory deficits. J Neurosurg. 71(1):105-12.
(WO 01/00612) 20010100
Langer et al., 1990, "New methods of drug delivery", Science. 249(4976):1527-33.
(0 747 363) 19961200
Taylor et al., 1984, "Respiratory syncytial virus infection in mice", Infect Immun. 43(2):649-55.
Daluge (5399580) 19950300
Schleicher et al., 1972, "Antiviral Activity in Tissue Culture Systems of bis-Benzimidazoles, Potent Inhibitors of Rhinoviruses", Microbiology 23:113-116.
Sparatore (3394141) 19680700
Harrison et al., 1965, "Nucleophilic substitution reactions of 2-chlorobenzimidazoles. Part II. Formation of benzimidazoine2-2thiones and related compounds", J. of the Chem. Society 3132-3135.
Maynard et al. (6423704) 20020700
(WO 96/00730) 19960100
Langer and Peppas, 1983, J Macromol. Sci. Rev. Marcomol. Chem. 23:61.
Levy et al., 1985, "Inhibition of calcification of bioprosthetic heart valves by local controlled-release diphosphonate", Science. 228(4696):190-2.
Pohl et al., 1992, "Respiratory syncytial virus infections in pediatric liver transplant recipients", J Infect Dis. 165(1):166-9.
Grey et al., 1980, "Outbreak of respiratory syncytial virus infection in the elderly", Br Med J. 281(6250):1253-4.
MacDonald et al., 1982, "Respiratory syncytial viral infection in infants with congenital heart disease", N Engl J Med. 307(7):397-400.
Navas et al., 1992, "Improved outcome of respiratory syncytial virus infection in a high-risk hospitalized population of Canadian children. Pediatric Investigators Collaborative Network on Infections in Canada", J Pediatr. 121(3):348-54.
Roderick et al., 1972, "Bisbenzimidazoles. Potent Inhibitors of Rhinoviruses", J. Med. Chem. 15:655-658.
U.S. Appl. No. 60/216,084, filed Jul. 6, 2000.
Feigen et al., eds., 1987, Textbook of Pediat. Infect. Disease, WB Saunders, Philadelphia, pp. 1653-1675.
Henderson et al., 1979, "Respiratory-syncytial-virus infections, reinfections and immunity. A prospective, longitudinal study in young children", N Engl J Med. 300(10):530-4.
Kuzmierkiewicz, W. "Oxidation Reaction of Benzimidazoline-2-Thione with Dimethyl Sulfoxide," Polish Journal of Chemistry 59(7-9):921-923 (1985).
Castellanos et al., 1985, "Nucleophlic substitution in quaternary salts of N,N′-linked biazoles and related systems", J. of the Chem. Society, 1209-1215.
Goodson et al., 1984, "The Scope of Dental Therapy", Med. Applications of Controlled Release, vol. 2, pp. 115-138.
(WO 96/40125) 19961200
Gordon et al. (5559256) 19960900
(WO 00/04900) 20000200
Layton et al., Journal of the Chemical Society [Section] C: Organic (1968), (5), pp. 611-614.
Groothuis et al., 1988, Respiratory syncytial virus infection in children with bronchopulmonary dysplasia', Pediatrics. 82(2):199-203.
Johnson et al., 1999, "A direct comparison of the activities of two humanized respiratory syncytial virus monoclonal antibodies: MEDI-493 and RSHZl9", J Infect Dis. Jul.; 180(1):35-40.
Sefton et al, 1987, "Implantable pumps", Crit Rev Biomed Eng. 14(3):201-40.
Hall et al., 1979, "Neonatal respiratory syncytial virus infection", N Engl J Med. 300(8):393-6.
Beaulieu et al. (6448281) 20020900
Jegham et al. (5280030) 19940100
(11 78 070) 19640900
(0 151 826) 19850800
Kane et al. (6194406) 20010200
During et al., 1989, "Controlled release of dopamine from a polymeric brain implant: in vivo characterization", Ann Neurol. 25(4):351-6.
Hall et al., 1981, "Modes of Transmission of Respiratory Synctial Virus", J. Pediatr. 99:101-103.
Sturm et al., Journal of Chromatography (1988), 430(1), pp. 43-51.
(WO 01/00611) 20010100
CA Registry No. 152072-57-6, entry date into the Registy file Jan. 4, 1994.
Lopez Bernstein et al., Liposomes in the Therapy of Infectious Diseases and Cancer, Lopez-Bernstein and Fidler eds, Liss, NY, pp. 353-465, pp. 317-327, 1989.
Takase et al. (5576322) 19961100
Hemming et al., 1995, "Hyperimmune globulins in prevention and treatment of respiratory syncytial virus infections", Clin Microbiol Rev.8(1):22-23.
Willitzer et al., 1978, "Synthese und antivirale Wirsamkeit von substituierten 5-ureido-und 5-thioureidobenzimidazolderivaten", Pharmazie 33:30-38.
Miller et al. (5545653) 19960800
Patterson et al., 1990, "Molecular mechanisms of action of ribavirin", Rev Infect Dis. 12(6):1139-46.
Matsunaga et al. (5852011) 19981200
(0 161 049) 19900200
Janssens et al. (4839374) 19890600
Hertz et al., 1989, "Respiratory syncytial virus-induced acute lung injury in adult patients with bone marrow transplants: a clinical approach and review of the literature", Medicine(Baltimore). 68(5):269-81.
Smith et al., 1991, "A controlled trial of aerosolized ribavirin in infants receiving mechanical ventilation for severe respiraotry syncytial virus infection", N Engl J Med.325(1):24-9.
(WO 97/24119) 19970700
Peigue-Lafeuille et al., 1990, "Severe respiratory syncytial virus pneumonia in an adult renal transplant recipient: successful treatment with ribavirin", Scand J Infect Dis. 22(1):87-9.
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