Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Carbohydrate doai
Reexamination Certificate
2006-08-15
2006-08-15
Peselev, Elli (Department: 1623)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Carbohydrate doai
C514S026000, C536S005000, C536S007400
Reexamination Certificate
active
07091187
ABSTRACT:
The present invention relates (a) to new compounds represented by Formula I:wherein M represents a macrolide subunit (macrolide moiety) derived from macrolide possessing the property of accumulation in inflammatory cells, S represents a steroid subunit (steroid moiety) derived from steroid drug with anti-inflammatory activity and L represents a linker molecule linking M and S, (b) to their pharmacologically acceptable salts, prodrugs and solvates, (c) to processes and intermediates for their preparation, and (d) to their use in the treatment of inflammatory diseases and conditions in humans and animals. Such compounds inhibit many cytokines and immune mediators involved in immune responses which cause inflammation, allergy, or alloimmunity, including without limitation IL-1, 2, 4, 5, 6, 10, 12, GMCSF, ICAM, and TNF-α. Importantly, anti-inflammatory steroids exert a direct anti-inflammatory effect through binding to the glucocorticosteroid receptor.
REFERENCES:
patent: 4474768 (1984-10-01), Bright
patent: 4710495 (1987-12-01), Bodor
patent: 5747467 (1998-05-01), Agouridas et al.
patent: 6228346 (2001-05-01), Zhang et al.
patent: 6273086 (2001-08-01), Ohki et al.
patent: 6297260 (2001-10-01), Bandarage et al.
patent: 6402733 (2002-06-01), Daugherty
patent: 2001/0006962 (2001-07-01), Myhren et al.
patent: 2004/0005641 (2004-01-01), Burnet et al.
patent: 2004/0033969 (2004-02-01), Burnet et al.
patent: 2004/0087517 (2004-05-01), Burnet et al.
patent: 2004/0186063 (2004-09-01), Gutke et al.
patent: 0283055 (1990-08-01), None
patent: 0771564 (1997-05-01), None
patent: 0775489 (1997-05-01), None
patent: 0 283 055 (1998-09-01), None
patent: 00680967 (1998-10-01), None
patent: 0 895 999 (1999-02-01), None
patent: 0984019 (2000-03-01), None
patent: 0984019 (2000-03-01), None
patent: 2 327 084 (1999-01-01), None
patent: WO 94/13690 (1992-06-01), None
patent: WO 92/13872 (1992-08-01), None
patent: WO 92/13873 (1992-08-01), None
patent: WO 94/14834 (1994-07-01), None
patent: WO-97/41255 (1997-11-01), None
patent: WO 98/56801 (1998-12-01), None
patent: WO 99/51616 (1999-10-01), None
patent: WO-99/64040 (1999-12-01), None
patent: WO 00/42055 (2000-07-01), None
patent: WO-00/64882 (2000-11-01), None
patent: WO-02/055531 (2002-07-01), None
patent: WO-03/070173 (2003-08-01), None
patent: WO-03/070174 (2003-08-01), None
patent: WO-03/070254 (2003-08-01), None
Burnet et al., “Conjugates of biologically active compounds, methods for their preparation and use, formulation, and pharmaceutical applications thereof,” U.S. Provisional Appl. No. 60/357,789, filed Feb. 15, 2002.
Brandt-Rauf et al., “Fluorescent Assay For Estimating the Binding of Erythromycin Derivatives to Ribosomes,” Antimicrobiol Agents and Chemotherapy, American Society for Microbiology, Washington, D.C., 14(1):88-94, (1978).
Gladue R. P. et al.,“In Vitro and In Vivo Uptake of Azithromycin (CP-62,993) by Phagocytic Cells: Possible Mechanism of Delivery and Release at Sites of Infection,”Antimicrob. Agents and Chemother.,33. 1989, 277-282.
Olsen K. M. et al., “Intrapulmonary Pharmacokinetics of Zithromycin in Healthy Volunteers Given Five Oral Doses,”Antimicrob. Agents and Chemother.,40, 1996, 2582-2585.
Mikasa, K. et al., “The anti-inflammatory effect of erythromycin in zymosan-induced peritonitis of mice,”J. Antimicrob. Chemother.,30, 1992, 339-348.
“Discussion, Genomic organization of axolotl 1g genes,”J. Immunol.,159, 1997, 3395-4005.
Takizawa, H. et al., “Erythromycin Modulates IL-8 Expression in Normal and Inflamed Human Bronchial Epithelial Cells,”Am. J. Respir. Crit. Care Med.,156, 1997, 266-271.
Labro, M.T., “Anti-inflammatory activity of macrolides: a new therapeutic potential?”J. Antimicrob. Chemother.,41, 1998, 37-46.
Cazzola, M., et al., “Potential role of macrolides in the treatment of asthma,”Mondaldi Arch. Chest Dis.,55, 2000, 231-236.
Avila, P.C. et al., “Macrolides, asthma, inflammation, and infection,”Ann. Allergy Asthma Immunol,84, 2000, 565-568.
Amayasu, H. et al., “Clarithromycin suppresses bronchial hyperresponsisveness associated with eosinophilic inflammation in patients with asthma,”Ann. Allergy, Asthma&Immunol,84, 2000, 594-598.
Shoji, T. et al., “Anti-inflammatory effect of roxithromycin in patients with aspirin-intolerant asthma,”Clin. Exp. Allergy,29, 999, 950-956.
Griffith, E.C., et al., “Yeast Three-Hybrid System for Detecting Ligand-Receptor Interactions,”Methods in Enzymology,328m 2000, 89-110.
Denis A. et al., “Synthesis and Antibacterial Activity of HMR 36K47, A New Ketolide Highly Potent Against Erythromycin-Resistant and Susceptible Pathogens,”Bioorg.&Med. Chem. Lett,9, 1999, 3075-3080.
Agouridas C. et al., “Synthesis and Antibacterial Activity of Ketolides (6-O-Methyl-3-oxoerythromycin Derivatives): A New Class of Antibacterials Highly Potent against Macrolide-Resistant and -Susceptible Respiratory Pathogens,”J. Med. Chem.,41, 1998, 4080-4100.
Sun, Or Y. et al.J. Med. Chem.2000, 43, 1045-1049.
McFarland, J. W. et al., “Repromicin Derivatives with Potent Antibacterial Activity againstPasteurella multocida,”J. Med. Chem.,50, 1997, 1041-1045.
Denis A. et al., Synthesis of 6-O-Methyl-Azithromycin and Its Ketolide Analogue via Beckmann Rearrangement of 9(E)-6-O-Methyl-Erythromycin Oxime,Bioorg.&Med. Chem. Lett.,8, 1998, 2427-2432.
Lartey et al., Synthesis of 4″-Deoxy Motilides: Identification of a Potent and Orally Active Prokinetic Drug Candidate,J. Med. Chem.,38, 1998, 1793-1798.
Kirst, H.A. et al., “34. Metabolism of macrolides,” Bryskier, A. J. et al., Ed.Macrolides, Chemistry, Pharmacology and Clinical Use; Bryskier, Arnette Blackwell: Paris, 1993; pp 485-491.
Ma, Z. et al., “Discovery and Development of Ketolides as a New Generation of Macrolide Antimicrobial Agents,”Current Medicinal Chemistry—Anti-Infective Agents,1, 2002, 15-34.
Pascual A. et al., “Uptake and intracellular activity of ketolide HMR 3647 in human phagocytic and non-phagocytic cells,”Clin. Microbiol. Infect.,7, 2001, 65-69.
Hand, W. L. et al., “Characteristics and mechanisms of azithromycin accumulation and efflux in human polymorphonuclear leukocytes,”Int. J. Antimicrob. Agents,18, 2001, 419-425.
Amsden, G. W., “Advanced-generation macrolides: tissue-directed antibiotics,”Int. J. Antimicrob. Agents,18, 2001, 11-15.
Johnson, J. D. et al., “Antibiotic uptake by alveolar macrophages,”J. Lab. Clin. Med.,95, 1980, 429-439.
Wildfeuer, A. et al., “Uptake of Azithromycin by Various Cells and its Intracellular Activity under In Vivo Conditions,”Antimicrob. Agents Chemother.,40, 1996, 75-79.
Scorneaux, B. et al., “Intracellular Accumulation, Subcellular Distribution, and Efflux of Tilmicosin in Chicken Phagocytes,”Poult. Sci.,77, 1998, 1510-1521.
Mtairag, E. M. et al., “Investigation of dirithromycin and erythromycylamine uptake by human neutrophils in vitro,”J. Antimicrob. Chemother.33, 1994, 523-536.
Anderson R. et al., “An in-vitro evaluation of the cellular uptake and intraphagocytic bioactivity of clarithromycin (A-56268, TE-031), a new macrolide antimicrobial agent,”J. Antimicrob. Chemother.,22, 1988, 923-933.
Tasaka, Y. et al., “Rokitamycin Uptake by Alveolar Macrophages,”Jpn. J. Antibiot.41, 1988, 836-840.
Harf, R. et al., “Spiramycin uptake by alveolar macrophages,”J. Antimicrob. Chemother.,22, 1988, 135-140.
Suzuki, T. et al., “General and facile method for determination of configuration of steroid-17-yl-methyl glycolates at C-20 based on kinetic examination,”Chem. Soc.,Perkin Trans. 1, 1998, 3831-3836.
McLean, H.M. et al., “Novel Fluorinated Antiinflammatory Steroid with Reduced Side Effects: Methyl 9α-Fluoroprednisolone-16-carboxylate,”J. Pharm. Sci.1994, 83, 476-480.
Litt
Makaruha Oresta
Markovic Stribor
Mercep Mladen
Mesic Milan
Poljak Visnja
Darby & Darby
Peselev Elli
Pliva-Istrazivacki Institut D.o.o.
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