Lipid-modified immune response modifiers
Assignee3M Innovative Properties Company
InventorPaul Wightman
Life of this patent
Estimating the term…
Abstract
Lipid-modified immune response modifier compounds, pharmaceutical compositions containing the compounds and methods of use of these compounds as immunomodulators, for inducing or inhibiting cytokine biosynthesis in animals and in the treatment of diseases including viral and neoplastic diseases, are disclosed.
Claims24
A compound of the following Formula I:
- wherein:
- R1 has the formula alkylene-L-R1-1, alkenylene-L-R1-1, or alkynylene-L-R1-1, wherein:
- the alkylene, alkenylene, and alkynylene groups are optionally interrupted with one or more —O— groups;
- L is a bond or a functional linking group selected from the group consisting of —NH—S(O)2—, —NH—C(O)—, —NH—C(S)—, —NH—S(O)2—NR3—, —NH—C(O)—NR3—, —NH—C(S)—NR3—, —NH—C(O)—O—, —O—, —S—, and —S(O)2—;
- and
- R1-1 is a linear or branched aliphatic group having at least 11 carbon atoms, optionally including one or more unsaturated carbon-carbon bonds;
- R″ is selected from the group consisting of:
- hydrogen;
- alkyl;
- alkenyl;
- aryl;
- heteroaryl;
- heterocyclyl;
- alkylene-Y-alkyl;
- alkylene-Y-alkenyl;
- alkylene-Y-aryl;
- and
- alkyl or alkenyl substituted by one or more substituents selected from the group consisting of:
- —OH;
- halogen;
- —N(R4)2;
- —C(O)—C1-10alkyl;
- —C(O)—O—C1-10alkyl;
- —N3;
- aryl;
- heteroaryl;
- heterocyclyl;
- —C(O)-aryl;
- and
- —C(O)-heteroaryl;
- wherein:
- Y is —O— or —S(O)0-2—;
- and each R4 is independently selected from the group consisting of hydrogen, C1-10alkyl, and C2-10alkenyl;
- RA and RB are each independently selected from the group consisting of:
- hydrogen,
- halogen,
- alkyl,
- alkenyl,
- alkoxy,
- alkylthio, and
- —N(R3)2;
- or when taken together, RA and RB form a fused aryl ring or heteroaryl ring containing one heteroatom selected from the group consisting of N and S wherein the aryl or heteroaryl ring is unsubstituted or substituted by one or more R groups;
- or when taken together, RA and RB form a fused 5- to 7-membered saturated ring, optionally containing one heteroatom selected from the group consisting of N and S, and unsubstituted or substituted by one or more R groups;
- each R is independently selected from the group consisting of
- halogen,
- hydroxy,
- alkyl,
- alkenyl,
- haloalkyl,
- alkoxy,
- alkylthio, and
- —N(R3)2;
- and
- each R3 is independently selected from the group consisting of hydrogen and alkyl;
- with the proviso that when L is —NH—S(O)2— and RA and RB join to form an unsubstituted benzene ring, R1-1 is a linear or branched aliphatic group having greater than 16 carbon atoms, optionally including one or more unsaturated carbon-carbon bonds;
- and with the further proviso that when L is —NH—C(O)— and RA and RB join to form an unsubstituted pyridine ring, R1-1 is a linear or branched aliphatic group having greater than 11 carbon atoms, optionally including one or more unsaturated carbon-carbon bonds;
- or a pharmaceutically acceptable salt thereof.
2-6. (canceled)
8-10. (canceled)
(canceled)
15-16. (canceled)
(canceled)
A compound of the following Formula III:
- wherein:
- R1 has the formula alkylene-L-R1-1, alkenylene-L-R1-1, or alkynylene-L-R1-1, wherein:
- the alkylene, alkenylene, and alkynylene groups are optionally interrupted with one or more —O— groups;
- L is a bond or a functional linking group selected from the group consisting of —NH—S(O)2—, —NH—C(O)—, —NH—C(S)—, —NH—S(O)2—NR3—, —NH—C(O)—NR3—, —NH—C(S)—NR3—, —NH—C(O)—O—, —O—, —S—, and —S(O)2—;
- and
- R1-1 is a linear or branched aliphatic group having at least 11 carbon atoms, optionally including one or more unsaturated carbon-carbon bonds;
- R is selected from the group consisting of
- halogen,
- hydroxy,
- alkyl,
- alkenyl,
- haloalkyl,
- alkoxy,
- alkylthio, and
- —N(R3)2;
- n is 0 to 4;
- R2 is selected from the group consisting of:
- hydrogen;
- alkyl;
- alkenyl;
- aryl;
- heteroaryl;
- heterocyclyl;
- alkylene-Y-alkyl;
- alkylene-Y-alkenyl;
- alkylene-Y-aryl;
- and
- alkyl or alkenyl substituted by one or more substituents selected from the group consisting of:
- —OH;
- halogen;
- —N(R4)2;
- —C(O)—C1-10alkyl;
- —C(O)—O—C1-10alkyl;
- —N3;
- aryl;
- heteroaryl;
- heterocyclyl,
- —C(O)-aryl;
- and
- —C(O)-heteroaryl;
- Y is —O— or —S(O)0-2—;
- each R4 is independently selected from the group consisting of hydrogen, C1-10alkyl, and C2-10alkenyl;
- and
- R3 is selected from the group consisting of hydrogen and alkyl;
- with the proviso that when L is —NH—S(O2)—, and n is 0, R1-1 is a linear or branched aliphatic group having at least 16 carbon atoms, optionally including one or more unsaturated carbon-carbon bonds;
- or a pharmaceutically acceptable salt thereof.
22-23. (canceled)
26-27. (canceled)
A method of vaccinating an animal comprising administering an effective amount of N-(2-{2-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethoxy}ethyl)hexadecanamide to the animal as a vaccine adjuvant.
30-32. (canceled)
Dependencies are inferred from the claim text.