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US 11,691,976 B2Granted
Coelenterazine analogues
AssigneePromega Corporation
InventorsJoel R. Walker, Thomas A. Kirkland, Wenhui Zhou, Mary P. Hall, Harry Tetsuo Uyeda
Life of this patent
Estimating the term…
Abstract
Described are coelenterazine analogues, methods for making the analogues, kits comprising the analogues, and methods of using the compounds for the detection of luminescence in luciferase-based assays.
Claims17
A compound of formula (II)
- or a tautomer or a salt thereof, wherein:
- Y is nitro, or —NRy1Ry2;
- p is 0, 1, 2, 3, or 4;
- q is 0, 1, 2, 3, 4, or 5;
- p+q is 1, 2, 3, 4, 5, 6, 7, 8, or 9;
- R3, at each occurrence, is independently halogen, CN, nitro, C1-10alkyl, C1-10haloalkyl, —ORA3, or —NRB3RC3;
- R4, at each occurrence, is independently halogen, CN, nitro, C1-10alkyl, C1-10haloalkyl, —ORA4, or —NRB4RC4;
- RA3 and RA4, at each occurrence, are independently H, C1-10haloalkyl, C3-12cycloalkyl, —C(O)C1-10alkyl, —C(O)C3-12cycloalkyl, or —C(O)C1-3alkylene-C3-12cycloalkyl, wherein each cycloalkyl is optionally substituted with 1-4 substituents independently selected from the group consisting of halogen, C1-4alkyl, and C1-4haloalkyl;
- RB3, RB4, RC3, and RC4, at each occurrence, are independently H, C1-10haloalkyl, C3-12cycloalkyl, —C(O)C1-10alkyl, —C(O)C3-12cycloalkyl, —C(O)C1-3alkylene-C3-12cycloalkyl, —SO2C1-10alkyl, —SO2C3-12cycloalkyl, or —SO2C1-3alkylene-C3-12cycloalkyl, wherein each cycloalkyl is optionally substituted with 1-4 substituents independently selected from the group consisting of halogen, C1-4alkyl, and C1-4haloalkyl;
- alternatively, RB3 and RC3 and/or RB4 and RC4, together with the nitrogen atom to which each attaches form a 4- to 8-membered saturated or partially unsaturated heterocyclic ring, optionally substituted with 1-4 substituents independently selected from the group consisting of C1-4alkyl, C1-4haloalkyl, oxo, —OH, and —OC1-4alkyl;
- Ry1 and Ry2, at each occurrence, are independently H, C1-10alkyl, C1-10haloalkyl, C3-12cycloalkyl, or —C1-3alkylene-C3-12cycloalkyl, wherein each cycloalkyl is optionally substituted with 1-4 substituents independently selected from the group consisting of halogen, C1-4alkyl, and C1-4haloalkyl;
- and
- alternatively, Ry1 and Ry2 together with the nitrogen atom to which each attaches form a 4- to 8-membered saturated or partially unsaturated heterocyclic ring, optionally substituted with 1-4 substituents independently selected from the group consisting of C1-4alkyl, C1-4haloalkyl, oxo, —OH, and —OC1-4alkyl.
10 more elements
A compound of formula:
- or a tautomer or salt thereof.
Dependencies are inferred from the claim text.