Granted Patent B2

US 7,307,169 · App. 10/751,388 · Granted Dec 11, 2007

Abstract

Claims (40)

1. An isotopically enriched N-substituted piperazine compound of the formula:

or a salt thereof wherein;

Y is a straight chain or branched C1-C6 alkyl group or a straight chain or branched C1-C6 alkyl ether group wherein the carbon atoms of the alkyl group or alkyl ether group are each independently optionally substituted with deuterium or fluorine atoms; and

each Z is independently hydrogen, fluorine, chlorine, bromine, iodine, an amino acid side chain, a straight chain or branched C1-C6 alkyl group that may optionally contain a substituted or unsubstituted aryl group wherein the carbon atoms of the alkyl and aryl groups are each independently optionally substituted with fluorine atoms, a straight chain or branched C1-C6 alkyl ether group that may optionally contain a substituted or unsubstituted aryl group wherein the carbon atoms of the alkyl and aryl groups are each independently optionally substituted with fluorine atoms or a straight chain or branched C1-C6 alkoxy group that may optionally contain a substituted or unsubstituted aryl group wherein the carbon atoms of the alkoxy and aryl groups are each independently optionally substituted with fluorine atoms;

wherein the N-methyl piperazine is isotopically enriched with one or more 13 C and/or 15 N atoms.

2. The compound of claim 1 , wherein the N-substituted piperazine is isotopically enriched with two or more atoms of 13 C and/or 15 N.

3. The compound of claim 1 , wherein the N-substituted piperazine is isotopically enriched with three or more atoms of 13 C and/or 15 N.

4. The compound of claim 1 , wherein the N-substituted piperazine is isotopically enriched with four or more atoms of 13 C and/or 15 N.

5. The compound of claim 1 , wherein each Z is independently hydrogen, fluorine, chlorine, bromine or iodine.

6. The compound of claim 1 , wherein each Z is independently hydrogen, methyl or methoxy.

7. The compound of claim 1 , wherein Y is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl.

8. The compound of claim 1 , wherein each nitrogen atom of the piperazine ring is independently 14 N or 15 N.

9. The compound of claim 1 of the formula:

or salt of any of the fore going.

10. The compound of claim 9 , wherein the compound is a mono-TFA salt, a mono-HCl salt, a bis-TFA salt or a bis-HCl salt.

11. The compound of claim 9 , wherein each incorporated heavy atom isotope is present in at least 80 percent isotopic purity.

12. The compound of claim 9 , wherein each incorporated heavy atom isotope is present in at least 93 percent isotopic purity.

13. The compound of claim 9 , wherein each incorporated heavy atom isotope is present in at least 96 percent isotopic purity.

14. The compound of claim 1 , wherein the N-substituted piperazine is a mono-TFA salt, a mono-HCl salt, a bis-HCl salt or a bis-TFA salt.

15. The compound of claim 1 , wherein each incorporated heavy atom isotope is present in at least 80 percent isotopic purity.

16. The compound of claim 1 , wherein each incorporated heavy atom isotope is present in at least 93 percent isotopic purity.

17. The compound of claim 1 , wherein each incorporated heavy atom isotope is present in at least 96 percent isotopic purity.

18. An isotopically enriched N-substituted piperazine compound of the formula:

or a salt thereof wherein;

Y is a straight chain or branched C1-C6 alkyl group or a straight chain or branched C1-C6 alkyl ether group wherein the carbon atoms of the alkyl group or alkyl ether group are each independently optionally substituted with deuterium or fluorine atoms; and

each Z is independently hydrogen, fluorine, chlorine, bromine, iodine, an amino acid side chain or a straight chain or branched C1-C6 alkyl group that may optionally contain a substituted or unsubstituted aryl group wherein the carbon atoms of the alkyl and aryl groups are each independently optionally substituted with fluorine atoms;

wherein the N-substituted piperazine is isotopically enriched with one or more 13 C atoms and/or 15 N atoms.

19. The compound of claim 18 , wherein each Z is hydrogen.

20. An isotopically enriched N-substituted piperazine compound of the formula:

or a salt thereof, wherein;

Y is a straight chain or branched C1-C6 alkyl group or a straight chain or branched CI-C6 alkyl ether group wherein the carbon atoms of the alkyl group or alkyl ether group are each independently optionally substituted with deuterium or fluorine atoms; and

each Z is independently hydrogen, fluorine, chlorine, bromine, iodine, an amino acid side chain or a straight chain or branched C1-C6 alkyl group that may optionally contain a substituted or unsubstituted aryl group wherein the carbon atoms of the alkyl and aryl groups are each independently optionally substituted with fluorine atoms; and

wherein the N-substituted piperazine is isotopically enriched with one or more 13 C atoms and/or 15 N atoms.

21. An isotopically enriched N-substituted piperazine compound of the formula:

or a salt thereof, wherein;

Y is a straight chain or branched C1-C6 alkyl group or a straight chain or branched C1-C6 alkyl ether group; and

each Z is independently hydrogen, fluorine, chlorine, bromine, iodine, an amino acid side chain, a straight chain or branched C1-C6 alkyl group, a straight chain or branched C1-C6 alkyl ether group or a straight chain or branched C1-C6 alkoxy group; and

wherein the N-substituted piperazine is isotopically enriched with one or more 13 C atoms and/or 15 N atoms.

22. An isotopically enriched N-substituted piperazine compound of the formula:

or a salt thereof, wherein the N-substituted piperazine is isotopically enriched with one or more 13 C atoms and/or 15 N atoms.

Assignments (11)