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US 2015/0031689 A1Published application
Peripherally restricted diphenyl purine derivatives
AssigneeResearch Triangle Institute
InventorsRangan Maitra, Alan Bradley Fulp, Yanan Zhang, Herbert H. Seltzman
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Abstract
The invention provides compounds capable of acting as antagonists at cannabanoid receptors according to the following formula: Such compounds may be used to treat conditions for which the cannabinoid receptor system has been implicated, such as obesity, liver disease, diabetes, pain, and inflammation.
Claims26
A compound according to the structure:
- wherein:
- each R1, R2, and R3 is H or a substituent independently selected from the group consisting of halo, OH, optionally substituted C1-10 alkyl, optionally substituted C1-10 alkoxy, optionally substituted C2-4 alkenyl, optionally substituted C2-4 alkynyl, NR6R7, NR6COR7, NR6CO2R7, CR6R7OR8, CONR6R7, CO2R6, CN, CF3, NO2, N3, C1-3 alkylthio, R9SO, R9SO2, CF3S, and CF3SO2;
- R4 is H or C1-10 alkyl;
- R5 is:
- or an optionally substituted piperidine ring, connected through a carbon atom;
- or R4 and R5 taken together form a piperidine ring with the nitrogen atom to which they are attached, wherein the piperidine ring is substituted with a substituent selected from the group consisting of NR6SO2R9, NR6CONR7R11, NR6COR15, and NR6CO2R7 and is optionally further substituted with one or more substituents independently selected from the group consisting of halo, OH, optionally substituted C1-10 alkyl, optionally substituted C1-10 alkoxy, optionally substituted C2-4 alkenyl, optionally substituted C2-4 alkynyl, optionally substituted aryl, optionally substituted aralkyl, optionally substituted alkaryl, NR6R7, NR6COR7, CR6R7OR8, CO2R6, CN, CF3, NO2, N3, C1-3 alkylthio, R9SO, R9SO2, CF3S, and CF3SO2, NR6SO2R9, NR6CONR7R11;
- NR6CO2R7, and CONR6R7;
- or R4 and R5 taken together form an optionally substituted thiomorpholine 1,1-dioxide ring;
- R6, R7, and R8 are independently selected from H and optionally substituted C1-10 alkyl;
- R9 is H, optionally substituted C1-10 alkyl, NR6R7, or NR6COR7;
- R10 is H or optionally substituted C1-10 alkyl;
- R11 is selected from the group consisting of H, optionally substituted C1-10 alkyl, and CR6R7CO2R8;
- R15 is optionally substituted C1-12 alkyl, optionally substituted C1-12 heteroalkyl, optionally substituted C1-6alkyl(amino), or optionally substituted aryl;
- L is a linker comprising an optionally substituted C1-15 alkyl or C1-15 heteroalkyl;
- and
- m and n are each independently integers from 0 to 5;
- or a pharmaceutically acceptable ester, amide, salt, solvate, prodrug, or stereoisomer thereof.
14 more elements
Dependencies are inferred from the claim text.