Synthesis of [1-
View Patent ↗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
1. A labeled compound of the formula
where C* are each 13 C,
X is selected from the group consisting of —NR 6 R 7 and —OR 8 wherein R 6 and R 7 are each independently selected from the group consisting of C 1 -C 4 lower alkyl, alkoxy and aryl and R 8 is selected from the group consisting of C 1 -C 4 lower alkyl, alkoxy and aryl, and
T is selected from the group consisting of —CH 3 , —CD 3 , —CH 2 —S—R 9 , —CH 2 —S(O)—R 9 , and —CH 2 —(O)S(O)—R 9 wherein 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.
2. The compound of claim 1 wherein said aryl 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.
3. The compound of claim 1 wherein said aryl is phenyl.
4. A labeled compound of the formula
wherein the C* of the C*—X is 12 C and the C* of the C*-T is 13 C,
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 consisting of C 1 -C 4 lower alkyl, alkoxy and aryl and R 8 is selected from the group consisting of C 1 -C 4 lower alkyl, alkoxy and aryl, and
T is selected from the group consisting of —CH 3 , —CD 3 , —CH 2 —S—R 9 , —CH 2 —S(O)—R 9 , and —CH 2 —(O)S(O)—R 9 wherein 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.