Aminoalkyl glucosamine phosphate compounds and their use as adjuvants and immunoeffectors
AssigneeRibi ImmunoChem Research, Inc.
InventorsDavid A. Johnson, C. Gregory Sowell
Life of this patent
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Abstract
Aminoalkyl glucosamine phosphate compounds that are adjuvants and immunoeffectors are described and claimed. The compounds have a 2-deoxy-2-amino glucose in glycosidic linkage with an aminoalkyl (aglycon) group. Compounds are phosphorylated at the 4 or 6 carbon on the glucosamine ring and comprise three 3-alkanoyloxyalkanoyl residues. The compounds augment antibody production in immunized animals as well as stimulate cytokine production and activate macrophages. Methods for using the compounds as adjuvants and immunoeffectors are also disclosed.
Claims84
A compound having the following structure:
- ##STR3## wherein, X is selected from the group consisting of O and S;
- Y is selected from the group consisting of O and NH;
- n, m, p and q are integers from 0 to 6;
- R.sub.1, R.sub.2 and R.sub.3 are the same or different and are normal fatty acyl residues having from about 7 to about 16 carbon atoms;
- R.sub.4 and R.sub.5 are the same or different and are selected from the group consisting of H and methyl;
- R.sub.6 and R.sub.7 are the same or different and are selected from the group consisting of H, hydroxy, alkoxy, phosphono, phosphonooxy, sulfo, sulfooxy, amino, mercapto, cyano, nitro, formyl, carboxy, and esters and amides thereof;
- and R.sub.8 and R.sub.9 are the same or different and are selected from the group consisting of phosphono and H, and at least one of R.sub.8 and R.sub.9 is phosphono.
A method for enhancing the immune response of a mammal, wherein said immune response is selected from the group consisting of enhancing the generation of antibody in immunized animals, stimulating the production of cytokines and stimulating a cell-mediated immune response, comprising administering to the mammal an effective amount of a compound having the following structure:
- ##STR4## wherein, X is selected from the group consisting of O and S;
- Y is selected from the group consisting of O and NH;
- n, m, p and q are integers from 0 to 6;
- R.sub.1, R.sub.2, and R.sub.3 are normal fatty acyl residues having from about 7 to about 16 carbon atoms;
- R.sub.4 and R.sub.5 are the same or different and are selected from the group consisting of H and methyl;
- R.sub.6 and R.sub.7 are the same or different and are selected from the group consisting of H, hydroxy, alkoxy, phosphono, phosphonooxy, sulfo, sulfooxy, amino, mercapto, cyano, nitro, formyl and carboxy, and esters and amides thereof;
- R.sub.8 and R.sub.9 are the same or different and are selected from the group consisting of phosphono and H, and at least one of R.sub.8 and R.sub.9 is phosphono.
A vaccine composition comprising a compound having the following structure:
- ##STR5## wherein, X is selected from the group consisting of O and S;
- Y is selected from the group consisting of O and NH;
- n, m, p and q are integers from 0 to 6;
- R.sub.1, R.sub.2 and R.sub.3 are the same or different and are normal fatty acyl residues having from about 7 to about 16 carbon atoms;
- R.sub.4 and R.sub.5 are the same or different and are selected from the group consisting of H and methyl;
- R.sub.6 and R.sub.7 are the same or different and are selected from the group consisting of H, hydroxy, alkoxy, phosphono, phosphonooxy, sulfo, sulfooxy, amino, mercapto, cyano, nitro, formyl and carboxy, and esters and amides thereof;
- R.sub.8 and R.sub.9 are the same or different and are selected from the group consisting of phosphono and H, and at least one of R.sub.8 and R.sub.9 is phosphono, an antigen and a suitable carrier.
A pharmaceutical composition comprising a compound having the following structure:
- ##STR6## wherein, X is selected from the group consisting of O and S;
- Y is selected from the group consisting of O and NH;
- n, m, p and q are integers from 0 to 6;
- R.sub.1, R.sub.2 and R.sub.3 are normal fatty acyl residues having from about 7 to about 16 carbon atoms;
- R.sub.4 and R.sub.5 are the same or different and are selected from the group consisting of H and methyl;
- R.sub.6 and R.sub.7 are the same or different and are selected from the group consisting of H, hydroxy, alkoxy, phosphono, phosphonooxy, sulfo, sulfooxy, amino, mercapto, cyano, nitro, formyl and carboxy, and esters and amides thereof;
- R.sub.8 and R.sub.9 are the same or different and are selected from the group consisting of phosphono and H, and at least one of R.sub.8 and R.sub.9 is phosphono, and a pharmaceutically acceptable carrier.
Dependencies are inferred from the claim text.