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US 2014/0194628 A1Published application
Substituted imidazo ring systems and methods
Assignee3M Innovative Properties Company
InventorsLarry R. Krepski, Joseph F. Dellaria, Jr., Daniel E. Duffy, Matthew R. Radmer, David T. Amos
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Abstract
Imidazo ring systems substituted at the 1-position, pharmaceutical compositions containing the compounds, intermediates, methods of making the compounds, and methods of use of these compounds as immunomodulators, for inducing cytokine biosynthesis in animals and in the treatment of diseases including viral and neoplastic diseases are disclosed.
Claims18
A compound of the Formula (I-1):
- wherein:
- X is alkylene optionally interrupted by one or more —O— groups;
- Z is —C(O)—;
- R1-1 is selected from the group consisting of:
- hydrogen,
- alkyl,
- aryl,
- alkylene-aryl,
- heteroaryl,
- alkylene-heteroaryl, and
- alkyl, aryl, alkylene-aryl, heteroaryl, or alkylene-heteroaryl substituted by one or more substituents selected from the group consisting of:
- halogen,
- cyano,
- nitro,
- alkoxy,
- dialkylamino,
- alkylthio,
- haloalkyl,
- haloalkoxy, and
- alkyl;
- R2 is selected from the group consisting of:
- hydrogen,
- alkyl,
- alkenyl,
- alkylene-Y-alkyl,
- alkyene-Y-alkenyl, and
- alkyl or alkenyl substituted by one or more substituents selected from the group consisting of hydroxyl and halogen;
- RA and RB are each independently selected from the group consisting of:
- hydrogen,
- alkyl,
- alkenyl,
- alkoxy, and
- alkylthio;
- or RA and RB are taken together to form either a fused aryl ring that is unsubstituted or substituted by one or more R groups, or a fused 5 to 7 membered saturated ring that is unsubstituted or substituted by one or more Ra groups;
- R is selected from the group consisting of:
- fluoro,
- alkyl,
- haloalkyl,
- alkoxy, and
- —N(R9)2;
- and
- Ra is selected from the group consisting of:
- halogen,
- hydroxy,
- alkyl,
- alkenyl,
- haloalkyl,
- alkoxy,
- alkylthio, and
- —N(R9)2;
- Y is selected from the group consisting of —O— and —S(O)0-2—;
- and
- R9 is selected from the group consisting of hydrogen and alkyl;
- or a pharmaceutically acceptable salt thereof.
51 more elements
A compound of the Formula (Ia):
- wherein:
- X is alkylene optionally interrupted by one or more —O— groups;
- n is an integer from 0 to 1;
- R1-1 is alkyl;
- R is fluoro;
- R2 is selected from the group consisting of:
- hydrogen,
- alkyl,
- alkylene-O-alkyl, and
- alkyl substituted by one or more substituents selected from the group consisting of hydroxyl and halogen;
- or a pharmaceutically acceptable salt thereof.
8 more elements
The compound 5-(4-Amino-2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)-4,4-dimethylpentan-2-one;
- or a pharmaceutically acceptable salt thereof.
Dependencies are inferred from the claim text.