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US 10,308,975 B2Granted
Substituted imidazo[1,2-a]pyrazines as luciferase substrates
AssigneePromega Corporation
InventorsAnton Shakhmin, Thomas Kirkland, Joel Walker, Thomas Machleidt, Mary Hall, Keith V. Wood
Life of this patent
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Abstract
Described are substituted imidazo[1,2-a]pyrazine compounds, which are coelenterazine analogs, kits comprising the compounds, and methods of using the compounds for the detection of luminescence in luciferase-based assays. Also described are methods for making the compounds, such as a method using aminopyrazine acetophosphonates as synthesis intermediates.
Claims16
A compound of formula (I):
- or a tautomer or pharmaceutically acceptable salt thereof,
- wherein:
- R1 is phenyl;
- and
- q is 1;
- wherein said phenyl is substituted with 1, 2, 3, 4, or 5 functional groups independently selected from the group consisting of cyano, carbamate, nitro, alkyl, alkenyl, alkynyl, haloalkyl, haloalkoxy, heteroalkyl, cycloalkyl, cycloalkenyl, aryl, heteroaryl, heterocyclyl, heterocycloalkyl, cycloalkylalkyl, heteroarylalkyl, arylalkyl, hydroxy, hydroxyalkyl, alkoxy, allyloxy, aryloxy, benzyloxy, amino, aminoalkyl, sulfonylamino, sulfinylamino, sulfonyl, sulfinyl, —COOH, amide, carbamate, silyl, silyloxy, sulfanyl, and acyl;
- provided that R1 is not
- wherein Rc is OH, OC(O)C1-C7-alkyl, or OCH2OC(O)C1-C7-alkyl.
5 more elements
A compound of formula (I):
- or a tautomer or pharmaceutically acceptable salt thereof,
- wherein:
- R1 is phenyl;
- and
- q is 1;
- wherein said phenyl is substituted with 2, 3, 4, or 5 functional groups independently selected from the group consisting of halogen, cyano, carbamate, nitro, alkyl, alkenyl, alkynyl, haloalkyl, haloalkoxy, heteroalkyl, cycloalkyl, cycloalkenyl, aryl, heteroaryl, heterocyclyl, heterocycloalkyl, cycloalkylalkyl, heteroarylalkyl, arylalkyl, hydroxy, hydroxyalkyl, alkoxy, allyloxy, aryloxy, benzyloxy, amino, aminoalkyl, sulfonylamino, sulfinylamino, sulfonyl, sulfinyl, —COOH, amide, carbamate, silyl, silyloxy, sulfanyl, and acyl.
3 more elements
Dependencies are inferred from the claim text.