Derivatives of monosaccharides as cell adhesion inhibitors

Details Derivatives of monosaccharides as cell adhesion inhibitors Derivatives of monosaccharides as cell adhesion inhibitors

2006-05-02

2006-05-02

Wilson, James O. (Department: 1623)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Carbohydrate doai

C514S023000, C514S025000, C536S124000, C536S018700, C536S004100, C536S017200, C536S053000, C536S123000, C536S123100, C536S120000, C536S116000

Reexamination Certificate

active

07037899

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: 6590085 (2003-07-01), 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, “Phenylisocyanate derivatives of carbohydrates”, Acta. Chem. Scand. 1961, 15, pp 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-a-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 aluminium hydride-aluminium 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 responses in vivo,”Proc. Natl. Acad. Sci(USA), 88:8072 (1991).
Hasegawa et al, Synthesis of N-[2-S-(2-Acetamido-2,3-Dideoxy-D-Gluopyranose-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/Chodroitin/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 α 5 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 anitgen 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).

Affiliated with

Also associated with

Rating

Derivatives of monosaccharides as cell adhesion inhibitors does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Derivatives of monosaccharides as cell adhesion inhibitors, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Derivatives of monosaccharides as cell adhesion inhibitors will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3535677