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US 8,809,529 B2Granted
Imidazo[1,2-α]pyrazine derivatives
AssigneePromega Corporation
InventorsDieter H. Klaubert, Poncho Meisenheimer, James Unch
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Abstract
The present invention provides, among other things, imidazo[1,2-α]pyrazine derivatives according for Formula (Ia) or Formula (Ib). The derivatives are useful in any method which other coelenterazines have been used. For example, the derivatives may be used in a bioluminogenic method to detect the presence of certain compounds or molecules.
Claims26
A compound of formula (Ia) or formula (Ib):
- wherein R2 is selected from the group consisting of
- or C2-5 straight chain alkyl;
- R6 is selected from the group consisting of —H, —OH, —NH2, —OC(O)R or —OCH2OC(O)R;
- R8 is selected from the group consisting of —CH2C6H5, H or lower cycloalkyl;
- W is —NH2, halo, —OH, —NHC(O)R, —CO2R;
- X is —S—, —O— or —NR22—;
- Y is —H, —OH, or —OR11;
- Z is —CH— or —N—;
- each R11 is independently —C(O)R″ or —CH2OC(O)R″;
- R22 is H;
- each R is independently C1-7 straight-chain alkyl or C3-7 branched alkyl;
- R″ is C1-7 straight-chain alkyl or C3-7 branched alkyl;
- with the proviso that when R2 is
- or
- R8 is not —CH2C6H5;
- with the proviso that when R2 is —CH2C6H5, R8 is lower cycloalkyl;
- and
- with the proviso that when R6 is NH2, R2 is,
- or C2-5 straight chain alkyl;
- or R8 is not —CH2C6H5.
17 more elements
A compound of formula (Ia) or formula (Ib):
- wherein R2 is selected from the group consisting of
- R6 is selected from the group consisting of —H, —OH, —NH2, —OC(O)R or —OCH2OC(O)R;
- R8 is selected from the group consisting of —CH2C6H5, —C(R3)(R4)H, H or lower cycloalkyl;
- wherein R3 and R4 are both H or both C1-2 alkyl;
- X is —NR22—;
- Z is —CH— or —N—;
- R22 is CH3 or CH2CH3;
- each R is independently C1-7 straight-chain alkyl or C3-7 branched alkyl;
- each R11 is independently —C(O)R″ or —CH2OC(O)R″;
- and
- R″ is C1-7 straight-chain alkyl or C3-7 branched alkyl.
8 more elements
A compound of formula (Ia) or formula (Ib):
- wherein R2 is selected from the group consisting of
- or C2-5 straight chain alkyl;
- R6 is selected from the group consisting of —H, —OH, —NH2, —OC(O)R or —OCH2OC(O)R;
- R8 is selected from the group consisting of —CH2C6H5, —C(R3)(R4)H, H or lower cycloalkyl;
- wherein R3 and R4 are both H or both C1-2 alkyl;
- W is —NH2, halo, —OH, —NHC(O)R, —CO2R;
- X is —S—, —O— or —NR22—;
- Y is —H;
- Z is —CH— or —N—;
- each R11 is independently —C(O)R″ or —CH2OC(O)R″;
- R22 is H;
- each R is independently C1-7 straight-chain alkyl or C3-7 branched alkyl;
- R″ is C1-7 straight-chain alkyl or C3-7 branched alkyl;
- with the proviso that when R2 is —CH2C6H5, R8 is —C(R3)(R4)H or lower cycloalkyl;
- and
- with the proviso that when R6 is NH2, R2 is,
- or C2-5 straight chain alkyl;
- or R8 is not —CH2C6H5.
15 more elements
A compound selected from
A compound of formula
A compound selected from:
Dependencies are inferred from the claim text.