1222. Bimosiamose

Nomenclature

CAS number: 187269-40-5
3′,3'''-(1,6-Hexanediyl)bis[6′-(α-d-mannopyranosyloxy)[1,1′-biphenyl]]-3-acetic acid; 1,6-bis[3-(3-carboxymethylphenyl)-4-(2-α-d-mannopyranosyloxy)phenyl]hexane; TBC-1269.
C46H54O16; mol wt 862.91.
C 64.03%, H 6.31%, O 29.67%.

Description and references

Pan-selectin receptor antagonist. Prepn: T. P. Kogan et al., WO 9701335; eidem, US 5919768 (1997, 1999 both to Texas Biotechnol.); eidem, J. Med. Chem. 41, 1099 (1998). Stereospecific synthesis: I. L. Scott et al., Carbohydr. Res. 317, 210 (1999). Review of pharmacology and clinical development: L. Pradella, Curr. Opin. Anti-Inflam. Immunomod. Invest. Drugs 1, 56-60 (1999); E. Aydt, G. Wolff, Pathobiology 70, 297-301 (2003). Clinical pharmacokinetics: M. Meyer et al., Int. J. Clin. Pharmacol. Ther. 43, 463 (2005). Clinical evaluation in allergic asthma: K. M. Beeh et al., Pulm. Pharmacol. Ther. 19, 233 (2006).

Chemical structure

Properties

White solid, mp 115-117°.

Derivative

Disodium salt.

Nomenclature

CAS number: 187269-60-9
TBC-1269z.
C46H52Na2O16; mol wt 906.88.
C 60.92%, H 5.78%, Na 5.07%, O 28.23%.

Properties

Slightly hygroscopic white powder, mp 243-245°.

Therapeutic Category

Anti-inflammatory

Keywords

Anti-inflammatory (Biological Response Modifier)