Modulators of the complement system comprising polyhexaose arylene sulfate derivatives

A compound selected from those of the formula:

• ##STR9## wherein Y is selected from the group consisting of H and --COCH.sub.3 ;
• n is an integer 2 or 3;
• and B is an arylene selected from the group consisting of:
• ##STR10##

A process for the preparation of compounds of the formula:

• ##STR13## wherein X is --SO.sub.3 M and M is a nontoxic pharmaceutically acceptable cation salt, wherein the salt forming moiety is selected from the group consisting of alkali metal, alkaline earth metal, aluminum, ammonia and substituted ammonia selected from the group consisting of trialkylamine (C.sub.1 -C.sub.6), piperidine, pyrazine, alkanolamine (C.sub.2 -C.sub.6) and cycloalkylamine (C.sub.3 -C.sub.6);
• n is an integer 2 or 3;
• and B is an arylene selected from the group consisting of:
• ##STR14## which comprises reacting an arylene compound resorcinol di-trimethylsilylether and an appropriate acetylated sugar octaacetylmaltose with boron trifluoride etherate in methylene chloride, at ambient temperature for 4-30 hours, giving a 1,3-bis[4-O-(2,3,4,6-tetra-O-acetyl-.alpha.(or .beta.)-D-glucopyranosyl)-2,3,6-tri-O-acetyl-.alpha.(or .beta.)-D-glucopyranosyl-1-oxy]-arylene, then reacting with metallic sodium in methanol at 0.degree. C. for about one hour, giving a 1,3-bis[4-O-.alpha.(or .beta.)-D-glucopyranosyl-.alpha.(or .beta.)-D-glucopyranosyl-1-oxy]-arylene derivative;
• reacting with a trialkylamine (C.sub.1 -C.sub.6) compound triethylamine-sulfur trioxide in N,N-dimethylacetamide at 50.degree.-75.degree. C. for 10-20 hours, under an inert atmosphere and adding to acetone, giving a polykis(H-sulfate), polytriethylamine salt;
• then reacting with a cation-containing compound wherein the salt forming moiety is selected from the group consisting of alkali metal, alkaline earth metal, aluminum, ammonia and substituted ammonia selected from the group consisting of piperidine, pyrazine, alkanolamine (C.sub.2 -C.sub.6) and cycloalkylamine (C.sub.3 -C.sub.6), and precipitating in ethanol, giving the final products.