SYNTHESIS OF 1-13 CPYRUVIC ACID, 2-13CPYRUVIC ACID, 3-13CPYRUVIC ACID AND COMBINATIONS THEREOF

摘要

The present invention is directed to labeled compounds, of the formulae: (A, B, C) wherein C* is each independently selected from the group consisting of 13C and 12C with the proviso that at least one C* is 13C, each hydrogen of the methylene group can independently be either hydrogen or deuterium, the methyl group includes either zero or three deuterium atoms, Q is from the group of sulfide, sulfinyl, and sulfone, Z is an aryl group from the group of 1 -naphthyl, substituted 1-naphthyl, 2-naphthyl, substituted 2-naphthyl, and phenyl groups with the structure: (D) wherein R1, R2, R3, R4 and R5 are each independently from the group of hydrogen, a C1-C4 lower alkyl, a halogen, and an amino group from the group of NH2, NHR and NRR' where R and R' are each independently from the group of a C1-C4 lower alkyl, a phenyl, and an alkoxy group, and the methyl group can include either zero or three deuterium atoms. The present invention is also directed to labeled compounds of the formula: (E) or (F) where X is from the group of NR6R7 and -OR8 where R6 and R7 are each independently selected from the group of C1-C4 lower alkyl, alkoxy and aryl and R8 is from the group of C1-C4 lower alkyl, alkoxy and aryl, T is from the group of -CH3, - CD3, -CH2-S-R9, -CH2-S(O)-R9, and -CH2-(O)S(O)-R9, J is from the group of -CH(OH)-CH2-S-R9, -CH(OH)-CH2-S(O)-R9, and -CH(OH)-CH2-(O)S(O)-R9 where R9 is an aryl group from the group of 1-naphthyl, substituted 1-naphthyl, 2-naphthyl, substituted 2-naphthyl, and phenyl groups with the structure: (G) wherein R1, R2, R3, R4 and R5 are each independently from the group of hydrogen, a C1-C4 lower alkyl, a halogen, and an amino group from the group of NH2, NHR and NRR' where R and R' are each independently from the group of a Cl-C4 lower alkyl, a phenyl, and an alkoxy group, and C* are each independently selected from the group consisting of 13C and 12C with the proviso that at least one C* is 13C.