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US 8,569,304 B2Granted
Active esters of N-substituted piperazine acetic acids, including isotopically enriched versions thereof
AssigneeDH Technologies Development Pte. Ltd.
InventorsSubhakar Dey, Darryl J. C. Pappin, Subhasish Purkayastha, Sasi Pillai, James M. Coull
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Abstract
In some embodiments, this invention pertains to active esters of N-substituted piperazine acetic acid, including isotopically enriched versions thereof. In some embodiments, this invention pertains to methods for the preparation of active esters of N-substituted piperazine acetic acid, including isotopically enriched versions thereof.
Claims48
An N-substituted piperazine acetic acid active ester compound of the formula:
- or a salt thereof, wherein;
- LG is the leaving group of an active ester;
- X is O or S;
- 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 each independently comprise linked hydrogen, deuterium or fluorine atoms;
- each Z is independently hydrogen, deuterium, 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 each independently comprise linked hydrogen, deuterium or 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 each independently comprise linked hydrogen, deuterium or 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 alkyl and aryl groups each independently comprise linked hydrogen, deuterium or fluorine atoms;
- and
- the N-substituted piperazine acetic acid active ester is isotopically enriched with one or more heavy atom isotopes.
4 more elements
A method comprising:
- reacting an N-substituted piperazine acetic acid compound of the formula:
- or a salt thereof, with:
- 1) a compound of the formula:
- and, if the piperazine compound is a salt,
- 2) optionally with a base strong enough to deprotonate the basic nitrogen atoms of the piperazine ring;
- to thereby form an N-substituted piperazine acetic acid active ester of the formula:
- or a salt thereof wherein;
- Hal is a fluorine, chlorine, bromine or iodine;
- LG is the leaving group of an active ester;
- X is O or S;
- 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 each independently comprise linked hydrogen, deuterium or fluorine atoms;
- each Z is independently hydrogen, deuterium, 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 each independently comprise linked hydrogen, deuterium or 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 each independently comprise linked hydrogen, deuterium or 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 alkyl and aryl groups each independently comprise linked hydrogen, deuterium or fluorine atoms;
- and optionally the N-substituted piperazine acetic acid moiety comprises one or more heavy atom isotopes;
- and
- optionally treating the N-substituted piperazine acetic acid active ester with an acid.
12 more elements
Dependencies are inferred from the claim text.