American Cyanamid Company

Vijay G Nair

Seymour Bernstein

Joseph P Joseph

John F Poletto

Bosco S Wang

Arthur J Lewis

V M Ruszala-Mallon

Ramson B Conrow

This disclosure described novel derivatives of dibenzothiophene, dibenzothiophene sulfoxide, dibenzothiophene sulfone, thioxanthene, thioxanthene sulfoxide and thioxanthene sulfone which are active as modulators of the mammalian immune response system.

Substituted dibenzothiophenes

Rutin poly(H-)sulfate and salts thereof useful as complement inhibitors.

Rutin poly(H-)sulfate salts and related compounds

Hydroxyalkyl ether derivatives of rutin poly(H-)sulfate and salts thereof useful as complement inhibitors.

Hydroxyalkyl ether derivatives of rutin poly(H-)sulfate and method of use

6'-(1-Adamantanecarboxylate)-6-O-.alpha.-D-galactopyranosyl-.alpha.-D-gluco pyranose sulfate salts, useful as complement inhibitors, and the process for making such compounds.

6'-(1-Adamanta

Mono-, di- and tri-adamantylcarbonyl- digalactopyranosyl- glucopyranosyl- fructofuranose sulfate salts, useful as complement inhibitors and the process of making such compounds.

Mono-, di- and tri-adamantylcarbonyl- digalactopyranosyl-

O-.alpha.-D-Galactopyranosyl(1.fwdarw.6)-O-.alpha.-D-galactopyranosyl(1.fwd arw.6)-O-.alpha.-D-glucopyranosyl(1.fwdarw.2)-O-.beta.-D-fructofuranosyl(1. fwdarw.6)-O-.alpha.-D-glucopyranosyl(1.fwdarw.4)-O-.alpha.-D-glucopyranosyl -.alpha.-D-glucopyranoside sulfate salts useful as complement inhibitors and the process of making such compounds.

O-.alpha.-D-Multigalactopyranosyl-O-.alpha.-D-multiglucopyranosyl-O-.beta.-

O-.beta.-D (and O-.alpha.-D) multi-galactopyranosyl (or xylopyranosyl or glucopyranosyl) 1.alpha.,1.alpha.' galactopyranosyl (or xylopyranosyl or glucopyranosyl) sulfate salts, useful as complement inhibitors, the intermediates thereof and the process for preparation of such compounds.

O-.beta.. -D (and O-.alpha... -D) Multigalactopyranosyl, xylopyranosyl

O-.alpha.-D-glucopyranosyl(1.fwdarw.4)-[O-.alpha.-D-glucopyranosyl-(1.fwdar w.4)].sub.n -O-.beta.-D-glucopyranosyl(1.fwdarw.6)-.beta.-D-fructofuranosyl-O-.alpha.- D-galactopyranosyl(1.fwdarw.6)-.alpha.-D-glucopyranoside sulfate salts, useful as inhibitors of the complement system and the process of making such compounds.

Multi-glucopyranosyl-fructofuranosyl-galactopyranosyl-glucopyranoside

Carbalkoxymethyl derivatives of rutin poly(H-)sulfate and salts thereof useful as complement inhibitors.

Carbalkoxymethyl derivatives of rutin poly(H-)sulfate and method of use

Carboxyalkyl derivatives of rutin polyl(H-)sulfate and salts thereof useful as complement inhibitors.

Carboxyalkyl derivatives of rutin poly(H-)sulfate

Rutin poly(H--)sulfate and salts thereof useful as complement inhibitors.

Rutin poly(H--)sulfate salts and related compounds

D-Erythro-2,3-dihydroxy-1-[substituted and unsubstituted)-1-phenyl-1H-pyrazolo[3,4-b]quinoxalin-3-yl]propyl-4-O-.alph a.-D-glucopyranosyl-.alpha.-D-glucopyranoside poly(H-sulfate)salts useful as complement inhibitors.

D-Erythro-2,3-dihydroxy-1-(1-phenyl-1H-pyrazolo(3,4-b)quinoxalin-3-y

D-Erythro-2,3-dihydroxy-1-(and 3-) (1-phenyl-1H-pyrazolo[3,4-b]quinoxalin-3-yl)propyl-.beta.-D-glucopyranosid e (and .alpha.-D-galactopyranoside) poly(H-sulfate)salts useful as complement inhibitors.

D-Erythro-2,3-dihydroxy-1-(and 3-)

O-.alpha.-D (and O-.beta.-D) multi-galactopyranosyl (and glucopyranosyl) 1.fwdarw.4 (and 1.fwdarw.6) galactopyranosyl 1.fwdarw.6-.alpha.-D-glucopyranose sugars and acetates thereof useful in the preparation of the corresponding sulfate salts which are useful as complement inhibitors.

Oligosaccharide precursors to substituted O-.alpha.-D and

O-.alpha.-D (and O-.beta.-D) multi-galactopyranosyl (and glucopyranosyl) 1.fwdarw.4 (and 1.fwdarw.6) galactopyranosyl 1.fwdarw.6-.alpha.-D-glucopyranose sulfate salts which are useful as complement inhibitors.

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New York, NY, United States of America

Vijay G Nair