Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Reexamination Certificate
2006-02-28
2006-02-28
Wilson, James O. (Department: 1623)
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
C536S018700, C536S004100, C536S017200, C536S053000, C536S123000, C536S123100, C536S120000, C536S116000, C514S025000
Reexamination Certificate
active
07005516
ABSTRACT:
This invention relates generally to compounds and processes for synthesizing derivatives of 2-3-O-isopropylidene-α-L-xylo-2-hexulofuranosonic acid. The compounds of this invention are useful, inter-alia, for the inhibition and prevention of cell adhesion and cell adhesion-mediated pathologies, including inflammatory and autoimmune diseases, such as bronchial asthma, rheumatoid arthritis, type I diabetes, multiple sclerosis, allograft rejection and psoriasis. This invention also relates to pharmacological compositions containing derivatives of 2-3-O-isopropylidene-α-L-xylo-2-hexulofuranosonic acid and the methods of treating such pathologies as listed above.
REFERENCES:
patent: 2715121 (1955-08-01), Glen et al.
patent: 4056322 (1977-11-01), Gordon et al.
patent: 4735934 (1988-04-01), Gordon
patent: 4996195 (1991-02-01), Ronsen et al.
patent: 5010058 (1991-04-01), Ronsen et al.
patent: 5637570 (1997-06-01), Arora et al.
patent: 379397 (1990-07-01), None
patent: 404136 (1990-12-01), None
patent: 219453 (1995-08-01), None
patent: WO 91/04862 (1991-04-01), None
patent: WO 92/00995 (1992-01-01), None
patent: WO 94/11381 (1994-05-01), None
Bouveng, Acta Chemica Scandinavica, 15, 1961, 96-100.
Abraham et al, “α4Integrins Mediate Antigen-induced Late Bronchial Responses and Prolonged Airway Hyperresponsiveness in Sheep,”J. Clin. Invest., 93:776 (1994).
Aspinall et al, “The hex-5-enose degradation: zinc dust cleavage of 6-deoxy-6-iodo-α-D-galactopyranosicid linkages in methylated di- and trisaccharides,”Can. J. Chem., 62:2728-2735 (1984).
Baron et al, “Surface Expression of α4 Integrin by CD4 T Cells is Required for Their Entry into Brain Parenchyma,”J. Exp. Med., 177:57 (1993).
Bhattacharjee and Gorin, “Hydrogenolysis of carbohydrate acetals, ketals, and cyclic orthoesters with lithium aluminum hydride-aluminum trichloride,”Can. J. Chem., 47:1195 (1969).
Binkley, “Synthesis of Methyl 2,6-Dideoxy-3-C-Mathyl-α-D-Ribo-Hexopyranoside (Methyl α-D-Mycaroside), A Component of the Antitumor Agent Mithramycin,”J. Carbohydr. Chem., 4:227 (1985).
Bouveng, “Phenylisocyanate Derivatives of Carbohydrates,”Acta. Chem. Scand., 15:96-100 (1961).
Chisolm et al, “Monoclonal antibodes to the integgrin α-4 subunit inhibit the murine contact hypersensitivity response,”Eur. J. Immunol., 23:682 (1993).
Ferguson et al, “Two integrin-binding peptides abrogate T cell-mediated immune responsesin vivo,” Proc. Natl. Acad. Sci(USA), 88:8072 (1991).
Hasegawa et al, Synthesis of N-[2-S-(2-Acetamido-2,3-Dideoxy-D-Glucopyranose-3-yl)-2-Thio-D-Lactoyl]-L-Alanyl-D-Isoglutamine,J. Carbohydr. Chem., 3:331-341 (1984).
King and Allbutt, “Stereochemistry of bimolecular nucleophilic opening of a dioxolenium ring fused to an anchored cyclohexane system,”Can. J. Chem., 47:1455 (1969).
King and Allbutt, “Remarkable stereoselectivity in the hydrolysis of dioxolenium ions and orthoesters fused to anchored six-membered rings,”Can. J. Chem., 48:1754 (1970).
Komoriya et al, “The Minimal Essence Sequence for a Major Cell Type-specific Adhesion Site (CS1) within the Alternatively Spliced Type III Connecting Segment Domain of Fibronectin Is Leucine-Aspartic Acid-Valine,”J. Biol. Chem., 266:15075 (1991).
Mani et al, “Heparan/Chondroitin/Dermatan Sulfate Primer 2-(6-Hydroxynaphthyl)-O-β-D-Xylopyranoside Preferentially Inhibits Growth of Transformed Cells,”Cancer Res., 58, pp. 1099-1104 (1998).
“Monosaccharides,”Methods in Carbohydr. Chem., 1:107 (1962) & 1:191 (1962).
Nowlin et al, “A Novel Cyclic Pentapeptide Inhibits α4β1 and α5 β 1 Integrin-mediated Cell Adhesion,”J. Biol. Chem., 268(27):20352 (1993).
Podolsky et al, “Attenuation of Colitis in the Cotton-top Tamarin by Anti-α4 integrin Monoclonan Antibody,”J. Clin. Invest., 92: 372 (1993).
Wahl et al, “Synthetic Fibronectin Peptides Suppress Arthritis in Rats by Interrupting Leukocyte Adhesion and Recruitment,”J. Clin. Invest., 94:655 (1994).
Yang et al, “Inhibition of insulitis and prevention of diabetes in nonobese diabetic mice by blocking L-selectin and very late antigen 4 adhesion receptors,”Proc. Natl. Acad. Sci.(USA), 90:10494 (1993).
Yednock et al, “Prevention of experimental autoimmune encephalomyelitis by antibodies against α4β1 integrin,”Nature(Lond), 356:63 (1992).
Arora Sudershan K
Kishore Nawal
Deshmukh Esq. Jayadeep R.
Heibel Esq. George E.
Khare Devesh
Ranbaxy Laboratories Limited
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