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US 6,664,264 B2Granted
Thioether substituted imidazoquinolines
Assignee3M Innovative Properties Company
InventorsJoseph F. Dellaria, Bryon A. Merrill, Matthew R. Radmer
Life of this patent
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Abstract
Imidazoquinoline and tetrahydroimidazoquinoline compounds that contain thioether functionality at the 1-position are useful as immune response modifiers. The compounds and compositions of the invention can induce the biosynthesis of various cytokines and are useful in the treatment of a variety of conditions including viral diseases and neoplastic diseases.
Claims34
A compound of the formula (I):
- wherein:
- X is —CHR3—, —CHR3-alkyl-, or —CHR3-alkenyl-;
- Z is —S—, —SO—, or —SO2—;
- R1 is selected from the group consisting of:
- -alkyl;
- -aryl;
- -heteroaryl;
- -heterocyclyl;
- -alkenyl;
- —R4-aryl;
- —R4-heteroaryl;
- —R4-heterocyclyl;
- R2 is selected from the group consisting of:
- -hydrogen;
- -alkyl;
- -alkenyl;
- -aryl;
- -heteroaryl;
- -heterocyclyl:
- -alkyl-Y-alkyl;
- -alkyl-Y-alkenyl;
- -alkyl-Y-aryl;
- and
- -alkyl or alkenyl substituted by one or more substituents selected from the group consisting of:
- —OH;
- -halogen;
- —N(R3)2;
- —CO—N(R3)2;
- —C—C1-10 alkyl;
- —CO—O—C1-10 alkyl;
- —N3;
- -aryl;
- -heteroaryl;
- -heterocyclyl;
- —CO-aryl;
- and
- —CO-heteroaryl;
- each R3 is independently H or C1-10 alkyl;
- each R4 is independently alkyl or alkenyl;
- each Y is independently —O— or —S(O)0-2—;
- n is 0 to 4;
- and
- each R present is independently selected from the group consisting of C1-10 alkyl, C1-10 alkoxy, hydroxy, halogen and trifluoromethyl;
- or a pharmaceutically acceptable salt thereof.
41 more elements
A compound selected from the group consisting of:
- 2-butyl-1-[4-(phenylthio)butyl]-1H-imidazo[4,5-c]quinolin-4-amine;
- 2-butyl-1-[2-(phenylthio)ethyl]-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin--4-amine;
- 2-butyl-1-[4-phenylsulfonyl)butyl]-1H-imidazo[4,5-c]quinolin-4-amine;
- 2-butyl-1-[4-(methylthio)butyl]-1H-imidazo[4,5-c]quinolin-4-amine;
- 2-butyl-1-[4-(methylsulfonyl)butyl]-1H-imidazo[4,5-c]quinolin-4-amine;
- 1-[2-(phenylthio)ethyl]-1H-imidazo[4,5-c]quinolin-4-amine;
- 1-[4-(phenylsulfonyl)butyl]-1H-imidazo[4,5-c]quinolin-4-amine;
- 1-[4-(methylsulfonyl)butyl]-1H-imidazo[4,5-c]quinolin-4-amine;
- 1-[4-(phenylthio)butyl]-1H-imidazo[4,5-c]quinolin-4-amine
- 1-[4-(methylthio)butyl]-1H-imidazo[4,5-c]quinolin-4-amine;
- 2-butyl-1-[5-(methylsulfonyl)pentyl]-1H-imidazo[4,5-c]quinolin-4-amine;
- 2-methyl-1-[5-(methylsulfonyl)pentyl]-1H-imidazo[4,5-c]quinolin-4-amine;
- 2-ethyl-1-[5-(methylsulfonyl)pentyl]-1H-imidazo[4,5-c]quinolin-4-amine;
- 1-[5-(methylsulfonyl)pentyl]-1H-imidazo[4,5-c]quinolin-4-amine;
- 2-hexyl-1 -[5-methylsulfonyl)pentyl]-1H-imidazo[4,5-c]quinolin-4-amine;
- 2-(2-methoxyethyl)-1-[5-(methylsulfonyl)pentyl]-1H-imidazo[4,5-c]quinolin-4-amine;
- 2-butyl-1-[5-(methylthio)pentyl]-1H-imidazo[4,5-c]quinolin-4-amine;
- 2-butyl-1-[5-(methylsulfinyl)pentyl]-1H-imidazo[4,5-c]quinolin-4-amine;
- 2-butyl-1-[3 -(methylsulfonyl)propyl]-1H-imidazo[4,5-c]quinolin-4-amine;
- and
- 2-butyl-1-[3-(phenylsulfonyl)propyl]-1H-imidazo[4,5-c]quinolin-4-amine;
- or a pharmaceutically acceptable salt thereof.
19 more elements
A compound of the formula (II):
- wherein:
- X is —CHR3—, —CHR3—alkyl-, or —CHR3-alkenyl-;
- Z is —S—, —SO—, or —SO2—;
- R1 is selected from the group consisting of;
- -alkyl;
- -aryl;
- -heteroaryl;
- -heterocyclyl;
- -alkenyl;
- —R4-aryl;
- —R4-heteroaryl;
- and
- —R4-heterocyclyl;
- R2 is selected from the group consisting of:
- -hydrogen;
- -alkyl;
- -alkenyl;
- -aryl;
- -heteroaryl;
- -heterocyclyl;
- -alkyl-Y-alkyl;
- -alkyl-Y-alkenyl;
- -alkyl-Y-aryl;
- and
- -alkyl or alkenyl substituted by one or more substituents selected from the group consisting of:
- —OH;
- -halogen;
- —N(R3)2;
- —CO—N(R3)2;
- —CO—C1-10 alkyl;
- —CO—O—C1-10 alkyl;
- —N3;
- -aryl;
- -heteroaryl;
- -heterocyclyl;
- —CO-aryl;
- and
- —CO-heteroaryl;
- each R3 is independently H or C1-10 alkyl;
- each R4 is independently alkyl or alkenyl;
- each Y is independently —O— or —S(O)0-2—;
- n is 0 to 4;
- and
- each R present is independently selected from the group consisting of C1-10 alkyl, C1-10 alkoxy, hydroxy, halogen and trifluoromethyl;
- or a pharmaceutically acceptable salt thereof.
42 more elements
Dependencies are inferred from the claim text.