US 7,501,399 B2
Immunoeffector compounds
David A. Johnson, Hamilton, Mont. (US); Jory Baldridge, Victor, Calif. (US); and C. Gregory Sowell, Mukilteo, Wash. (US)
Assigned to Corixa Corporation, Seattle, Wash. (US)
Filed on Sep. 11, 2006, as Appl. No. 11/519,275.
Application 11/519275 is a division of application No. 10/496620, granted, now 7,129,219, previously published as PCT/US01/24284, filed on Aug. 03, 2001.
Claims priority of provisional application 60/223056, filed on Aug. 04, 2000.
Prior Publication US 2007/0004914 A1, Jan. 04, 2007
This patent is subject to a terminal disclaimer.
Int. Cl. A01N 43/04 (2006.01); A61K 49/04 (2006.01)
U.S. Cl. 514—27  [514/23; 514/24; 514/25; 424/1.73; 424/9.43] 27 Claims
 
1. A method of inducing an immune response in a subject, the method comprising:
administering a composition comprising a therapeutically effective amount of a pharmaceutically acceptable carrier and a compound having the formula of:

OG Complex Work Unit Drawing
and pharmaceutically acceptable salts thereof, wherein X is a member selected from the group consisting of —O— and —NH—;
Y is a member selected from the group consisting of —O— and —S—;
R1, R2 and R3 are each members independently selected from the group consisting of (C2-C24)acyl;
R4 is a member selected from the group consisting of —H and —PO3R7R8, wherein R7 and R8 are each members independently selected from the group consisting of —H and (C1-C4)alkyl;
R5 is a member selected from the group consisting of —H, —CH3 and —PO3R9R10, wherein R9 and R10 are each members independently selected from the group consisting of —H and (C1-C4)alkyl;
R6 is selected from H, OH, (C1-C4)alkoxy, —PO3R11R12, —OPO3R11R12, —SO3R11, —OSO3R11, —NR11R12, —SR11, —CN, —NO2, —CHO, —CO2R11, and —CONR11R12, wherein R11 and R12 are each independently selected from H and (C1-C4)alkyl, with the proviso that when R4 is —PO3R7R8, R5 is other than —PO3R9R10;
wherein “*1”, “*2”, “*3” and “**” represent chiral centers;
wherein the subscripts n, m, p and q are each independently an integer from 0 to 6, with the proviso that the sum of p and m is from 0 to 6.