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US 10,308,606 B2Granted
PSMA-targeted NIR dyes and their uses
AssigneeOn Target Laboratories, LLC
InventorsSumith A. Kularatne, Pravin Gagare
Life of this patent
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Abstract
The present disclosure relates to prostate specific membrane antigen (PSMA) targeted compounds conjugated to near-infra red (NIR) dyes and methods for a method for synthesizing a compound of the formula:
Claims4
A method for synthesizing a compound of the formula:
- wherein n is 0, 1, 2, 3, or 4;
- further wherein R3, R4, and R5 are independently selected from the group consisting of H+, Na+, K+, and NH4+;
- R6, R7, R8, and R9 are independently selected from the group consisting of H+, Na+, K+, and NH4+;
- and R10H+;
- comprising the steps of:
- (a) reacting a compound of formula I:
- with a compound of formula:
- in the presence of a polar organic solvent, 1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate and N,N-Diisopropylethylamine under argon and
- (b) reacting the resulting compound with sodium carbonate and a dye compound of the formula
6 more elements
A method for synthesizing an isotopic form of a compound of the formula:
- wherein said isotopic form comprises one or more carbon and/or hydrogen isotopes selected from the group consisting of H2, H3, C13 and C14;
- further wherein n is 0, 1, 2, 3, or 4;
- further wherein R3, R4, and R5 are independently selected from the group consisting of H+, Na+, K+, and NH4+;
- R6, R7, R8, and R9 are independently selected from the group consisting of H+, Na+,K+, and NH4+;and R10H+;
- comprising the steps of:
- (a) reacting an isotopic form of a compound of formula:
- wherein said isotopic form comprises one or more carbon and/or hydrogen isotopes selected from the group consisting of H2, H3, C13 and C14,
- with an isotopic form of a compound of formula:
- wherein said isotopic form comprises one or more carbon and/or hydrogen isotopes selected from the group consisting of H2, H3, C13 and C14,
- in the presence of a polar organic solvent, 1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate and N,N-Diisopropylethylamine under argon to provide an isotopic form of a compound that comprises one or more carbon and/or hydrogen isotopes selected from the group consisting of H2, H3, C13 and C14,
- (b) reacting the isotopic form of the compound obtained in step (a) with sodium carbonate and an isotopic form of a dye compound of the formula:
- wherein said isotopic form comprises one or more carbon and/or hydrogen isotopes selected from the group consisting of H2, H3, C13 and C14.
9 more elements
A method for synthesizing a compound of the formula:
- wherein n is 0, 1, 2, 3, or 4
- (a) reacting a compound of formula
- with a compound of formula:
- in the presence of a polar organic solvent, 1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate and N,N -Diisopropylethylamine under argon
- (b) reacting the resulting compound thereof with sodium carbonate and a dye compound of the formula:
2 more elements
Dependencies are inferred from the claim text.