Intermediates for the preparation of lipoxin A 4 analogs

Organic compounds -- part of the class 532-570 series – Organic compounds – Fatty compounds having an acid moiety which contains the...

Reexamination Certificate

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Reexamination Certificate

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07928255

ABSTRACT:
This invention is directed to lipoxin A4analogs of the following formula (I) and (II):wherein R1, R2, R3, R4and R5are described herein. These analogs are useful in treating inflammatory and autoimmune disorders in humans. These analogs are also useful in treating pulmonary or respiratory tract inflammation in humans.

REFERENCES:
patent: 5441951 (1995-08-01), Serhan
patent: 6066466 (2000-05-01), Serhan et al.
patent: 6100296 (2000-08-01), Madara et al.
patent: 6831186 (2004-12-01), Bauman et al.
patent: 7223798 (2007-05-01), Bauman et al.
patent: WO 94/29262 (1994-12-01), None
patent: WO 95/01179 (1995-01-01), None
patent: WO 98/11049 (1998-03-01), None
patent: WO 00/54761 (2000-09-01), None
patent: WO 00/54767 (2000-09-01), None
patent: WO 00/55109 (2000-09-01), None
patent: WO 01/34144 (2001-05-01), None
patent: WO 01/34548 (2001-05-01), None
patent: WO 01/70664 (2001-09-01), None
Brezinski and Serhan, “Characterization of Lipoxins by Combined Gas Chromatography and Electron-capture Negative Ion Chemical Ionization Mass Spectrometry: Formation of Lipoxin A4by Stimulated Human Whole Blood,”Biological Mass Spectrometry 20: 45-52, 1991.
Buchmann, B. et al., “Synthesis of a Chemically and Metabolically Stable and Biologically Potent PGD2-Analogue,”Tetrahedron Letters 31(24): 3425-3428, 1990.
Colgan, S. et al., “Lipoxin A4Modulates Transmigration of Human Neutrophils across Intestinal Epthelial Monolayers,”Journal of Clinical Inverstigation 92: 75-82, 1993.
Ellis, C.K. et al., “Metabolism of Prostaglandin D2in the Monkey,”The Journal of Biological Chemistry 254(10): 4152-4163, May 25, 1979.
Fiore, S. et al., “Induction of Functional Lipoxin A4Receptors in HL-60 Cells,”Blood 81(12): 3395-3403, Jun. 15, 1993.
Fiore, S. et al., “Lipoxin Recognition Sites. Specific Binding of Labeled Lipoxin A4with Human Neutrophils,”The Journal of Biological Chemistry 267(23): 16168-16176, Aug. 15, 1992.
Krause, W. et al., “Biotransformation of the stable prostacyclin analogue, iloprost, in the rat,” Abstract fromDrug Metab. Dispos 12: 645-651, 1984. Abstract available at http://dmd.aspetjournals.org.
Liston and Roberts, “Metabolic Fate of Radiolabeled Postaglandin D2in a Normal Human Male Volunteer,”The Journal of Biological Chemistry 260(24): 13172-13180, 1985.
Maddox, J.F. et al., “Lipoxin A4Stable Analogs Are Potent Mimetics That Stimulate Human Monocytes and THP-1 Cells via a G-protein-linked Lipoxin A4Receptor,”The Journal of Biological Chemistry 272(11): 6972-6978, Mar. 14, 1997.
Madema, P. et al., “Influence of lipoxin A4and other lipoxygenase-derived eicosanoids on tissue factor expression,”Am. J. Physiol. Cell Physiol.279: C945-C953, 2000.
O'Sullivan, S. et al., “Analysis of prostaglandin D2metabolites in urine: Comparison between enzyme immunoassay and negative ion chemical ionization gas chromatography-mass spectrometry,”Prostaglandins&other Lipid Mediators 57: 149-165, 1999.
Serhan, C. et al., “Aspirin-triggered 15-epi-lipoxin A4and novel lipoxin B4stable analogs inhibit neutrophil-mediated changes in vascular permeability,”Advances in Experimental Medicine and Biology 469: 287-293, 1999.
Serhan, C. et al., “Design of Lipoxin A4Stable Analogs That Block Transmigration and Adhesion of Human Neutrophils,”Biochemistry 34: 14609-14615, 1995.
Serhan, C. et al., “Lipoxin A4Metabolism by Differentiated HL-60 Cells and Human Monocytes: Conversion to Novel 15-Oxo,and Dihydro Products,”Biochemistry 31: 6313-6319, 1993.
Skuballa, W. et al., “Synthesis of a New Chemically and Metabolically Stable Prostacyclin Analogue with High and Long-Lasting Oral Activity,”Journal of Medicinal Chemistry 29(3): 313-315, 1986.
Takano, T. et al., “Neutrophil-mediated Changes in Vascular Permeability Are Inhibited by Topical Application of Aspirin-triggered 15-epi-lipoxi A4and Novel Lipoxin B4Stable Analogues,”Journal of Clinical Investigation 101: 819-826, 1998.
Webber, S. et al., “The total synthesis of the lipoxins and related compounds,”Advances in Experimental Medicine and Biology 229: 61-77, 1988.
Bannenberg, G. et al., “Lipoxins and novel 15-epi-lipoxin analogs display potent anti-inflammatory actions after oral administration,”British Journal of Pharmacology 143(1): 43-52, 2004.
Fiorucci, S. et al., “A β-oxidation-resistant lipoxin A4analog treats hapten-induced colitis by attenuating inflammation and immune dysfunction,”Proc. Natl. Acad. Sci. USA 101(44): 15736-15741, Nov. 2, 2004.
Guilford, W.J. et al., “Novel 3-Oxa Lipoxin A4Analogues with Enhanced Chemical and Metabolic Stability Have Anti-inflammatory Activity in Vivo,”Journal of Medicinal Chemistry 47(8): 2157-2165, 2004.
Guilford, W.J. et al., “Second-generation beta-oxidation resistant 3-oxa-lipoxin A4analogs,”Prostaglandins, Leukotrienes and Essential Fatty Acids 73: 245-250, 2005.

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