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US 2008/0175852 A1Published application
Synthesis of phosphocholine ester derivatives and conjugates thereof
AssigneeThe United States of America as represented by the Department of Health and Human Services
InventorLouis J. Rezanka
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Abstract
Aspects of the present invention include methods of synthesizing phosphocholine analogues and the phosphocholine conjugates formed therefrom and their use in preventing infections caused by microorganisms.
Claims34
A method, comprising the steps of:
- contacting
- with phosphocholine to form
- and
- replacing R1 with
- to form
- wherein X is bromo, chloro, iodo, tosyl, or mesyl;
- R1 is H or alkyl;
- Y is -(CH2)n- optionally substituted at any one or more methylene unit with halo, alkyl, alkenyl, alkynyl, cycloalkyl, alkylcycloalkyl, heterocyclyl, heterocycloalkyl, aryl, aralkyl, aryloxy, heteroaryl, heteroaralkyl, perfluoroalkyl, alkylamido, acyl, acyloxy, alkanesulfonamido, alkoxy, perfluoroalkoxy, alkylamino, carboxamido, carboalkoxy, or carboxyalkyl, or optionally one or more methylene unit is replaced with 0, S, or NH, or a combination thereof;
- and
- n is an integer from 0 to 20;
- wherein the replacing step comprises
- wherein Z is an electron withdrawing group.
9 more elements
(canceled)
A method of synthesizing (p-nitrophenyl-6-O-phosphocholine)hydroxyhexanoate from 6-bromo-hexanoic acid in no more than two steps, comprising the steps of:
- reacting 6-bromo-hexanoic acid with phosphocholine to form 6-(O-phosphocholine)hydroxyhexanoic acid;
- and
- reacting the 6-(O-phosphocholine)hydroxyhexanoic acid with p-nitrophenyl trifluoroacetate.
A method of synthesizing (p-nitrophenyl-6-O-phosphocholine)hydroxyhexanoate from 6-bromo-hexanoic acid in no more than three steps, comprising the steps of:
- reacting ethyl-6-bromohexanoate with phosphocholine to form ethyl-6-(O-phosphocholine)hexanoate;
- deprotecting the ethyl-6-(O-phosphocholine)hexanoate acid to form 6-(O-phosphocholine)hydroxyhexanoic acid using a quaternary amine;
- and
- reacting the 6-(O-phosphocholine)hydroxyhexanoic acid with p-nitrophenyl trifluoroacetate.
1 more element
Dependencies are inferred from the claim text.