N-alkylation of acridans
AssigneeSiemens Healthcare Diagnostics Inc.
InventorAnand Natrajan
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Abstract
The present invention provides compounds used in the synthesis of chemiluminescent acridinium compounds and methods of producing these compounds. Specifically, methods are provided for the N-alkylation of acridan compounds using alkylating reagents. Typically, these alkylating reagents comprise a protected sulfonate group protected with an acid-labile protecting group.
Claims20
A method for the N-alkylation of an acridan compound comprising reacting said acridan compound with a protected sulfonate triflate compound having the structure of formula (R1):
- wherein G is an acid-labile protecting group;
- and
- —RL— is a C1-20 linear or branched bivalent hydrocarbon radicals;
- optionally substituted with one or more heteroatoms, and combinations thereof, and wherein RL optionally comprises a zwitterionic linker group;
- wherein said acridan has the structure of formula (A1):
- wherein “m” and “n” are independently 0-4 and at least one of “m” or “n” is greater than 0;
- R1 and R2 are independently selected from electron donating groups;
- and
- R3 is hydrogen or a C1-C45 hydrocarbon radical optionally substituted with one or more heteroatoms and wherein R3 may optionally comprise a zwitterionic group and/or a zwitterionic linker group.
An N-alkylated acridan compound having the structure:
- wherein G is an acid-labile protecting group;
- “m” and “n” are independently 0-4 and at least one of “m” or “n” is greater than 0;
- wherein Ω is O or N;
- —RL—is a C1-20 linear or branched bivalent hydrocarbon radicals;
- optionally substituted with one or more heteroatoms, and combinations thereof, and wherein RL optionally comprises a zwitterionic linker group;
- R1 and R2 are independently selected from electron donating groups;
- R4 is absent when Ω is O or hydrogen or a C1-C40 hydrocarbon radical optionally substituted with one or more heteroatoms, and wherein R4 and R5 may optionally comprise a zwitterionic group and/or a zwitterionic linker group;
- and
- R5 hydrogen or a C1-C40 hydrocarbon radical optionally substituted with one or more heteroatoms, and combinations thereof and wherein R4 and R5 may optionally comprise a zwitterionic group and/or a zwitterionic linker group.
An N-alkylated acridinium having the structure:
- wherein G is an acid-labile protecting group;
- “m” and “n” are independently 0-4 and at least one of “m” or “n” is greater than 0;
- wherein Ω is O or N;
- —RL—is a C1-20 linear or branched bivalent hydrocarbon radicals;
- optionally substituted with one or more heteroatoms, and combinations thereof, and wherein RL optionally comprises a zwitterionic linker group;
- R1 and R2 are independently selected from electron donating groups;
- R4 is absent when Ω is O or hydrogen or a C1-C40 hydrocarbon radical optionally substituted with one or more heteroatoms, and wherein R4 and R5 may optionally comprise a zwitterionic group and/or a zwitterionic linker group;
- and
- R5 hydrogen or a C1-C40 hydrocarbon radical optionally substituted with one or more heteroatoms, and combinations thereof and wherein R4 and R5 may optionally comprise a zwitterionic group and/or a zwitterionic linker group.
Dependencies are inferred from the claim text.