Nonsteroidal anti-inflammatory substances, compositions and...

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Carbohydrate doai

Reexamination Certificate

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C514S008100, C530S322000, C536S007200, C536S007400

Reexamination Certificate

active

07109176

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, D represents a nonsteroidal subunit (nonsteroidal moiety) derived from nonsteroid drug with anti-inflammatory, analgesic and/or antipyretic activity (NSAID) and L represents a linking group covalently linking M and D; (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.

REFERENCES:
patent: 4474768 (1984-10-01), Bright
patent: 5004731 (1991-04-01), Philippe et al.
patent: 6127355 (2000-10-01), Greenwald et al.
patent: 6566509 (2003-05-01), Griffin et al.
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: 0 283 055 (1998-09-01), None
patent: 0 895 999 (1999-02-01), None
patent: 0984019 (2000-03-01), None
patent: 1 046 394 (2000-10-01), None
patent: 2 327 084 (1999-01-01), None
patent: WO-97/41255 (1997-11-01), None
patent: WO 98/56801 (1998-12-01), None
patent: WO-99/28308 (1999-06-01), None
patent: WO-99/64040 (1999-12-01), None
patent: WO 00/64882 (2000-11-01), None
patent: WO-02/15700 (2002-02-01), 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
Burnett et al., “Conjugates of biologically active compounds, methods for their preparation and use, formation, and pharmaceutical applications thereof,” U.S. Appl. No. 60/357,789, filed Feb. 15, 2002.
Brandt-Rauf et al., “Fluorescent Assay For Estimating the Binding of Erythromycin Derivatives to Ribosomes,” Antimicrobial 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.
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.
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, Amette 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.
Scormeaux, 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 erythromyclamine uptake by human neutrophilsin 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 (A56268, 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 9 α-Fluoroprednisolone-16-carboxylate,”J. Pharm. Sci.1994, 83, 476-480.
Little, R.J. et al., “Soft Drugs Based on Hydrocortisone: The Inactive Metabolite Approach and Its Application to Steroidal Antiinflammatory Agents,”Pharm. Res.,16, 1999, 961-967.
Kertesz, D.J. et al., “Thiol Esters from Steroid 17β-Carboxylic Acids: Carboxylate Activation and Internal Participation by 17α-Acylates,”J. Org. Chem.,51, 1986, 2315-2328.
Phillips, G. et al., “Synthesis and Structure—Activity Relationships in a Series of Antiinflammatory Corticosteroid Analogues, Halomethyl Androstane-17 β-carbothioates and 17β-carboselenoates,”J. Med. Chem.37, 1994, 3717-3729.
Bright, G.M. et al., “Synthesis, In Vitro and In Vivo Activity of Novel 9-Deoxo-9a-AZA-9a-Homoerythromycin A Derivatives; A new Class of Macrolide Antibiotics, The Azalides”J. Antibiot.,41, 1998, 1029-1047.
Costa, A.M. et al., “Hybrids of macrolides and nucleobases or nucleosides,”Tetrahedron Letters,41, 2000, 3371-3375.
Luong et al., “Treatment options for Rheumatoid Arthritis: Celecoxib, Leflunomide, Etanercept, and Infliximab,”Ann. Pharmacother.34, 2000, 743-760.
Taketo, M.M., “Cyclooxygenase 2 Inhibitors in Tumorigenesis (Part II),”J. Natl. Cancer Inst.90, 1998, 1609-1620.
Fournier, J., “COX-2 and Colon Cancer: Potential Targets for Chemoprevention,”J. Cell Biochem. Suppl.34, 2000,97-102.
Carswell, E.A., et al., “An endotoxin-induced serum factor that causes necrosis of tumors,”Proc. Natl. Acad. Sci. USA72, 1975, 3666-3670.
Elliot, M., et al., “Randomised double-blind comparison of chimeric monoclonal antibody to tum

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