Synthesis of [1-13c]pyruvic acid], [2-13c]pyruvic acid], [3-13c]pyruvic acid] and combinations thereof
Abstract
The present invention is directed to the labeled compounds, wherein C* is each either 13 C and 12 C where at least one C* is 13 C, each hydrogen of the methylene group is hydrogen or deuterium, the methyl group includes either zero or three deuterium atoms, Q is sulfide, sulfinyl, or sulfone, Z is an aryl group such as 1-naphthyl, substituted 1-naphthyl, 2-naphthyl, substituted 2-naphthyl, or a phenyl group wherein R 1 , R 2 , R 3 , R 4 and R 5 are each independently either hydrogen, a C 1 -C 4 lower alkyl, a halogen, and an amino group such as NH 2 , NHR and NRR′ where R and R′ are each independently either a C 1 -C 4 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 the labeled compounds
Claims
exact text as granted — not AI-modified1 - 5 . (canceled)
6 . A labeled compound of the formula
wherein C* is each independently selected from the group consisting of 13 C and 12 C with the proviso that at least one C* is 13 C, the methyl group includes either zero or three deuterium atoms, Q is selected from the group consisting of sulfide, sulfinyl, and sulfone, and Z is an aryl group selected from the group consisting of 1-naphthyl, substituted 1-naphthyl, 2-naphthyl, substituted 2-naphthyl, and phenyl groups with the structure
wherein R 1 , R 2 , R 3 , R 4 and R 5 are each independently selected from the group consisting of hydrogen, a C 1 -C 4 lower alkyl, a halogen, and an amino group from the group consisting of NH 2 , NHR and NRR′ where R and R′ are each independently selected from the group consisting of a C 1 -C 4 lower alkyl, a phenyl, and an alkoxy group.
7 . The compound of claim 6 wherein Z is selected from the group consisting of phenyl groups with the structure
wherein R 1 , R 2 , R 3 , R 4 and R 5 are each independently selected from the group consisting of hydrogen, a C 1 -C 4 lower alkyl, a halogen, and an amino group from the group consisting of NH 2 , NHR and NRR′ where R and R′ are each independently selected from the group consisting of a C 1 -C 4 lower alkyl, a phenyl, and an alkoxy group.
8 . The compound of claim 6 wherein Z is phenyl.
9 . A labeled compound of the formula
wherein C* is each independently selected from the group consisting of 13 C and 12 C with the proviso that at least one C* is 13 C, the methylene group includes zero or one deuterium atom, the methyl group includes either zero or three deuterium atoms, Q is selected from the group consisting of sulfide, sulfinyl, and sulfone, and Z is an aryl group selected from the group consisting of 1-naphthyl, substituted 1-naphthyl, 2-naphthyl, substituted 2-naphthyl, and phenyl groups with the structure
wherein R 1 , R 2 , R 3 , R 4 and R 5 are each independently selected from the group consisting of hydrogen, a C 1 -C 4 lower alkyl, a halogen, and an amino group from the group consisting of NH 2 , NHR and NRR′ where R and R′ are each independently selected from the group consisting of a C 1 -C 4 lower alkyl, a phenyl, and an alkoxy group.
10 . The compound of claim 9 wherein Z is selected from the group consisting of phenyl groups with the structure
wherein R 1 , R 2 , R 3 , R 4 and R 5 are each independently selected from the group consisting of hydrogen, a C 1 -C 4 lower alkyl, a halogen, and an amino group from the group consisting of NH 2 , NHR and NRR′ where R and R′ are each independently selected from the group consisting of a C 1 -C 4 lower alkyl, a phenyl, and an alkoxy group.
11 . The compound of claim 9 wherein Z is phenyl.
12 - 14 . (canceled)
15 . A labeled compound of the formula
where X is selected from the group consisting of —NR 6 R 7 and —OR 8 where R 6 and R 7 are each independently selected from the group of C 1 -C 4 lower alkyl, alkoxy and aryl and R 8 is selected from the group of C 1 -C 4 lower alkyl, alkoxy and aryl, J is selected from the group consisting of —CH(OH)—CH 2 —S—R 9 , —CH(OH)—CH 2 —S(O)—R 9 , and —CH(OH)—CH 2 —(O)S(O)—R 9 where R 9 is an aryl group selected from the group consisting of 1-naphthyl, substituted 1-naphthyl, 2-naphthyl, substituted 2-naphthyl, and phenyl groups with the structure
wherein R 1 , R 2 , R 3 , R 4 and R 5 are each independently selected from the group consisting of hydrogen, a C 1 -C 4 lower alkyl, a halogen, and an amino group from the group consisting of NH 2 , NHR and NRR′ where R and R′ are each independently selected from the group consisting of a C 1 -C 4 lower alkyl, a phenyl, and an alkoxy group, and C* are each independently selected from the group consisting of 13 C and 12 C with the proviso that at least one C* is 13 C.
16 . The compound of claim 15 wherein said R 9 is selected from the group consisting of phenyl groups with the structure
wherein R 1 , R 2 , R 3 , R 4 and R 5 are each independently selected from the group consisting of hydrogen, a C 1 -C 4 lower alkyl, a halogen, and an amino group from the group consisting of NH 2 , NHR and NRR′ where R and R′ are each a C 1 -C 4 lower alkyl, a phenyl, or an alkoxy group.
17 . The compound of claim 15 wherein said R 9 is phenyl.Join the waitlist — get patent alerts
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