Linked cyclitols and their polysulfated derivatives

US7173019B2 · kind B2 · utility

Assignee

• The Australian National University · AU

Inventors

• Martin Banwell · Canberra, AU
• Ligong Liu · Calle de la Era, AU
• Christopher Richard Parish · Campbell, AU
• Craig Geoffrey Freeman · Weston Creek, AU

Key dates

• Filing date: Jul 4, 2002
• Grant date: Feb 6, 2007
• Expiry date: Dec 11, 2022

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C2601/16
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The invention relates to compounds of the following formula (I). In these compounds, R1, R2, R3 and R4 are each independently a substituted or unsubstituted cyclitol with a ring comprising six carbon atoms, or hydrogen, substituted or unsubstituted alkyl, cycloalkyl, aryl, acyl, alkyloxycarbonyl, or alkylaminocarbonyl. At least two of R1, R2, R3 and R4 comprise the substituted or unsubstituted cyclitol. The linker can be any one of the following: —(CH2)w—, —(CH2)x—C6H4—(CH2)x—, —(CH2)y—NR5—(CH2)y—, and —(CH2)z—HCR6—(CH2)z—; wherein: w, x, y and z are independently an integer having a value of 0–10; R5 is a substituted or unsubstituted cyclitol with a ring comprising six carbon atoms; and, R6 is —OH, —OSO3Na, —OSO3Na substituted with alkyl, cycloalkyl or aryl, or substituted or unsubstituted alkyl, cycloalkyl or aryl. The compounds can also include substituted or unsubstituted cyclitol carbamides with the linker bond at the carbamide nitrogen. In other embodiments, the invention provides pharmaceutical compositions which include the compounds, and use of the compounds in the prevention or treatment in a mammalian subject of a disorder resulting from angiogenesis, metastasis, inflamm…