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US 12,016,952 B2Granted
Methods of preparing a monodisperse oligo(ethylene glycol) reagent composition
AssigneeNektar Therapeutics
InventorsMichael D. Bentley, Tacey X. Viegas, Richard R. Goodin, Lin Cheng, Xuan Zhao
Life of this patent
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Abstract
Methods of preparing monodisperse oligomer reagent compositions such as oligo(ethylene glycol) reagent compositions are described herein. The methods involve reacting a halo-terminated oligomer such as an oligo(ethylene oxide) having (m) monomers with a hydroxyl-terminated oligomer such as a hydroxyl-terminated oligo(ethylene oxide) having (n) monomers.
Claims11
A method of preparing a monodisperse oligo(ethylene glycol) reagent composition, comprising:
- (i) reacting a halo-terminated oligo(ethylene glycol) having (m) monomer subunits and a C1-C2 alkoxy (methoxy or ethoxy) end-capping group with a first hydroxyl-terminated oligo(ethylene glycol), HO—(CH2CH2O)n—H, having (n) monomer subunits, under conditions effective to displace the halo group from the halo-terminated oligo(ethylene glycol) to thereby form an oligo(ethylene glycol) having (m)+(n) monomer subunits (OEGm+n), wherein reacting the halo-terminated oligo(ethylene glycol) with the first hydroxyl-terminated oligo (ethylene glycol) comprises adding a 1:1 molar ratio of the halo-terminated oligo(ethylene glycol) to the first hydroxyl-terminated oligo (ethylene glycol) in a solution, where halo is selected from chloro, bromo, and iodo;
- (ii) converting the terminal hydroxyl group of OEGm+n into a halo group, —X, to form OEGm+n−X;
- and
- (iii) reacting OEGm+n−X with a second hydroxyl-terminated oligo(ethylene glycol) having (n) monomer subunits under conditions effective to displace the halo group of OEGm+n−X to thereby form an oligo(ethylene glycol) having (m)+2(n) monomer subunits (OEGm+2n), wherein reacting the OEGm+n−X with the second hydroxyl-terminated oligo (ethylene glycol) comprises adding a 1:1 molar ratio of OEGm+n−X to the second hydroxyl-terminated oligo (ethylene glycol) in a solution;
- where (m) and (n) each independently range from 1-6 in each occurrence, and (OEGm+2n) corresponds to a structure CH3(CH2)0,1O(CH2CH2O)m+2nH, and is present as part of a monodisperse composition of CH3(CH2)0,1O(CH2CH2O)m+2nH.
2 more elements
Dependencies are inferred from the claim text.