Novel 2,2', 2"-[s-phenenyltris(sulfonylimino)tris]-[2-deoxy-α-D-glucopyranose], dodecakis (H-sulfate) compounds and their salts

Claim 1

A compound of the formula: ##STR4## wherein R is a moiety selected from the group consisting of --SO 3 H.N(CH 3 ) 3 and --SO 3 X, wherein X is selected from the group consisting of alkali metal; and the pharmaceutically acceptable salts thereof.

Claim 8

A method of inhibiting the complement system in a body fluid which comprises subjecting said body fluid to the action of an effective complement inhibiting amount of a pharmaceutically acceptable compound of the formula: ##STR5## wherein R is a moiety selected from the group consisting of --SO 3 H.N(CH 3 ) 3 and --SO 3 X, wherein X is selected from the group consisting of alkali metal; and the pharmaceutically acceptable salts thereof.

Claim 9

A method of inhibiting the complement system in a body fluid which comprises subjecting said body fluid to the action of an effective complement inhibiting amount of a pharmaceutically acceptable compound of the formula: ##STR5## wherein R is a moiety selected from the group consisting of --SO 3 H.N(CH 3 ) 3 and --SO 3 X, wherein X is selected from the group consisting of alkali metal; and the pharmaceutically acceptable salts thereof.

Claim 13

A method of inhibiting the complement system in a warm-blooded animal which comprises internally administering to said animal an effective complement inhibiting amount of a pharmaceutically acceptable compound of the formula: ##STR6## wherein R is a moiety selected from the group consisting of --SO 3 H.N(CH 3 ) 3 and --SO 3 X, wherein X is selected from the group consisting of alkali metal; and the pharmaceutically acceptable salts thereof.

Claim 14

A method of inhibiting the complement system in a warm-blooded animal which comprises internally administering to said animal an effective complement inhibiting amount of a pharmaceutically acceptable compound of the formula: ##STR6## wherein R is a moiety selected from the group consisting of --SO 3 H.N(CH 3 ) 3 and --SO 3 X, wherein X is selected from the group consisting of alkali metal; and the pharmaceutically acceptable salts thereof.

Claim 18

A method for the preparation of a compound of the formula: ##STR7## wherein R is a moiety selected from the group consisting of --SO 3 H.N(CH 3 ) 3 and --SO 3 X, wherein X is selected from the group consisting of alkali metal; and the pharmaceutically acceptable salts thereof; which comprises reacting tetra-o-acetyl glucosamine with 1,3,5-benzenetrisulfonyl chloride in a weakly basic polar solvent; concentrating said solvent and precipitating the tetraacetyl trisulfonyl derivative from ice water and extracting into methylene dichloride; evaporating said solvent and dissolving said derivative in cold C 1 -C 6 alkanol saturated with ammonia; chilling for 24 hours, introducing nitrogen gas to remove ammonia, and evaporating to a thick oil; purifying said oil from water with activated charcoal, filtering and then drying to afford 2,2',2"-[s-phenenyltris(sulfonylimino)]tris[2-deoxy-D-glucopyranose]; reacting said glucopyranose with trimethylamine sulfur trioxide in dimethylformamide at 65° to 70° for 18 hours, and precipitating from C 1 -C 6 alkanol to afford 2,2',2"-[s-phenenyltris(sulfonylimino)]tris[2-deoxy-α-D-glucopyranose], dodecakis (H-sulfate) with trimethylamine and treating said trimethylammonium salt with sodium acetate in an aqueous medium for several minutes, and precipitating from C 1 -C 6 alkanol to afford 2,2',2"-[s-phenenyltris(sulfonylimino)]tris[2-deoxy-α-D-glucopyranose], dodecakis (H-sulfate) dodecasodium salt.

Claim 19

A method for the preparation of a compound of the formula: ##STR7## wherein R is a moiety selected from the group consisting of --SO 3 H.N(CH 3 ) 3 and --SO 3 X, wherein X is selected from the group consisting of alkali metal; and the pharmaceutically acceptable salts thereof; which comprises reacting tetra-o-acetyl glucosamine with 1,3,5-benzenetrisulfonyl chloride in a weakly basic polar solvent; concentrating said solvent and precipitating the tetraacetyl trisulfonyl derivative from ice water and extracting into methylene dichloride; evaporating said solvent and dissolving said derivative in cold C 1 -C 6 alkanol saturated with ammonia; chilling for 24 hours, introducing nitrogen gas to remove ammonia, and evaporating to a thick oil; purifying said oil from water with activated charcoal, filtering and then drying to afford 2,2',2"-[s-phenenyltris(sulfonylimino)]tris[2-deoxy-D-glucopyranose]; reacting said glucopyranose with trimethylamine sulfur trioxide in dimethylformamide at 65° to 70° for 18 hours, and precipitating from C 1 -C 6 alkanol to afford 2,2',2"-[s-phenenyltris(sulfonylimino)]tris[2-deoxy-α-D-glucopyranose], dodecakis (H-sulfate) with trimethylamine and treating said trimethylammonium salt with sodium acetate in an aqueous medium for several minutes, and precipitating from C 1 -C 6 alkanol to afford 2,2',2"-[s-phenenyltris(sulfonylimino)]tris[2-deoxy-α-D-glucopyranose], dodecakis (H-sulfate) dodecasodium salt.