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US 2020/0263229 A1Published application
Coelenterazine analogues
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 analogues, kits comprising the analogues, and methods of using the compounds for the detection of luminescence in luciferase-based assays. Also described are methods from making the compounds, such as a method using aminopyrazine acetophosphonates as synthesis intermediates.
Claims34
A compound of formula (I)
- or a tautomer, or a pharmaceutically acceptable salt thereof, wherein
- R1 is alkyl, alkenyl, alkynyl, aryl, bicyclic aryl, tricyclic aryl, heteroaryl, bicyclic heteroaryl, tricyclic heteroaryl, heterocycle, cycloalkyl, heteroarylcarbonyl, or phosphonate;
- and
- q is 0-2;
- wherein said alkyl, alkenyl, alkynyl, aryl, bicyclic aryl, tricyclic aryl, heteroaryl, bicyclic heteroaryl, tricyclic heteroaryl, heterocycle, cycloalkyl, heteroarylcarbonyl, and phosphonate, at each occurrence, are independently substituted or unsubstituted;
- provided that if q is 0, then
- R1 is not C1-C5 alkyl or
- wherein Ra is NH2, halogen, OH, NHC(O)C1-C7-alkyl, or CO2C1-C7-alkyl;
- provided that if q is 1, then
- R1 is not C1-C4 alkyl,
- wherein Rc is H, OH, OC(O)C1-C7-alkyl, OCH2OC(O)C1-C7-alkyl, X is S, O, NH, NCH3, or NCH2CH3, and Z is CH or N;
- and
- provided that if q is 2, then
- R1 is not C1-C3 alkyl;
- and wherein the compound of formula (I) is not 8-benzyl-2-((1-methyl-1H-imidazol-2-yl)methyl)-6-phenylimidazo[1,2-a]pyrazin-3(7H)-one.
12 more elements
A method of preparing a compound of formula (I),
- wherein R1 is alkyl, alkenyl, alkynyl, aryl, bicyclic aryl, tricyclic aryl, heteroaryl, bicyclic heteroaryl, tricyclic heteroaryl, heterocycle, cycloalkyl, heteroarylcarbonyl, or phosphonate;
- and
- q is 0-2;
- the method comprising:
- converting compound (vi)
- to a compound of formula (I).
3 more elements
A method of preparing a compound of formula (I),
- wherein R1 is alkyl, alkenyl, alkynyl, aryl, bicyclic aryl, tricyclic aryl, heteroaryl, bicyclic heteroaryl, tricyclic heteroaryl, heterocycle, cycloalkyl, heteroarylcarbonyl, or phosphonate;
- and
- q is 0-2;
- the method comprising:
- converting compound (xi)
- to a compound of formula (I).
3 more elements
Dependencies are inferred from the claim text.