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US 7,125,558 B2Granted
Process for the preparation of activated polyethylene glycols
AssigneeBioartificial Gel Technologies Inc.
InventorsMarie-Pierre Faure, Micheal Ibea
Life of this patent
Estimating the term…
Abstract
The present invention relates to a process for the preparation of activated polyethylene glycols, or PEG(NPC)2s, comprising reacting polyethylene glycol with an activator while in the presence of an aromatic nitrogen containing heterocyclic base. The process is carried out at temperatures ranging from about 20 to about 30° C., more preferably at room temperature, and under stoichiometric conditions.
Claims23
A process for preparing a bis-activated polyethylene glycol having the formula:
- Y-Q-O—(CH2—CH2—O)n-Q-Y
- wherein
- n is an integer between 4 and 800;
- Y is selected from the group consisting of a halide group, a mesyl group, a tosyl group, an imidazolyl group, an N-hydroxy-succinimidyl group, a phenoxyl group, and a substituted phenoxyl group;
- and
- Q is selected from the group consisting of SO2, CO(CHR1)tSO2, CO—O—(CHR1)t—O—SO2, C(O), SO2(CHR1)tSO2, SO2—O—(CHR1)t—O—SO2, CO—O—(CHR1)t—CR2═CR3—(CHR4)t—O—CO, and SO2—O—(CHR1)t—CR2═CR3—(CHR4)t—O—SO2,
- wherein
- t is 1, 2, or 3;
- and
- R1, R2, R3 and R4 are independently selected from the group consisting of H, a lower alkyl group, a lower branched alkyl group, an aryl group, and an aralkyl group;
- the process consisting essentially of reacting under stoichiometric conditions a polyethylene glycol having the formula:
- H—(O—CH2—CH2—)n—OH
- wherein
- n is an integer between 4 and 800;
- with an activator having the formula of Y-Q-X;
- wherein
- X and Y independently are selected from the group consisting of a halide group, a mesyl group, a tosyl group, an imidazolyl group, an N-hydroxy-succinimidyl group, a phenoxyl group, and a substituted phenoxy group;
- and
- Q is selected from the group consisting of SO2, CO(CHR1)tSO2, CO—O—(CHR1)t—O—SO2, C(O), SO2(CHR1)tSO2, SO2—O—(CHR1)t—O—SO2, CO—O—(CHR1)t—CR2═CR3—(CHR4)t—O—CO, and SO2—O—(CHR1)t—CR2═CR3—(CHR4)t—O—SO2,
- wherein
- t is 1, 2, or 3;
- and
- R1, R2, R3, and R4 are independently selected from the group consisting of H, a lower alkyl group, a lower branched alkyl group, an aryl group, and an aralkyl group;
- in the presence of a solvent and an aromatic nitrogen-containing heterocyclic base having the formula:
- wherein
- (NR5R6)c is located either in the ortho or para position;
- R5 and R6 are independently selected from the group consisting of a lower straight alkyl group, a lower branched alkyl group, an aryl group, and an aralkyl group;
- and
- c is 1 or 2;
- to produce said bis-activated polyethylene glycol.
27 more elements
A process for preparing a bis-activated polyethylene glycol having the formula:
- Y-Q-O—(CH2—CH2—O)n-Q-Y
- wherein
- n is an integer between 4 and 800;
- Y is selected from the group consisting of a halide group, a mesyl group, a tosyl group, an imidazolyl group, an N-hydroxy-succinimidyl group, a phenoxyl group, and a substituted phenoxyl group;
- and
- Q is selected from the group consisting of SO2, CO(CHR1)tSO2, CO—O—(CHR1)t—O—SO2, C(O), SO2(CHR1)tSO2, SO2—O—(CHR1)t—O—SO2, CO—O—(CHR1)t—CR2═CR3—(CHR4)t—O—CO, and SO2—O—(CHR1)t—CR2═CR3—(CHR4)t—O—SO2,
- wherein
- t is 1, 2, or 3;
- and
- R1, R2, R3 and R4 are independently selected from the group consisting of H, a lower alkyl group, a lower branched alkyl group, an aryl group, and an aralkyl group;
- the process consisting essentially of reacting a polyethylene glycol having the formula:
- H—(O—CH2—CH2—)n—OH
- wherein
- n is an integer between 4 and 800;
- with an activator having the formula of Y-Q-X;
- wherein
- X and Y are different and independently selected from the group consisting of a halide group, a mesyl group, a tosyl group, an imidazolyl group, an N-hydroxy-succinimidyl group, a phenoxyl group, and a substituted phenoxyl group;
- and
- Q is selected from the group consisting of SO2, CO(CHR1)tSO2, CO—O—(CHR1)t—O—SO2, C(O), SO2(CHR1)tSO2, SO2—O—(CHR1)t—O—SO2, CO—O—(CHR1)t—CR2═CR3—(CHR4)t—O—CO, and SO2—O—(CHR1)t—CR2═CR3—(CHR4)t—O—SO2,
- wherein
- t is 1, 2, or 3;
- and
- R1, R2, R3, and R4 are independently selected from the group consisting of H, a lower alkyl group, a lower branched alkyl group, an aryl group, and an aralkyl group;
- in the presence of a solvent and an aromatic nitrogen-containing heterocyclic base having the formula:
- wherein
- (NR5R6)c is located either in the ortho or para position;
- R5 and R6 are independently selected from the group consisting of a lower straight alkyl group, a lower branched alkyl group, an aryl group, and an aralkyl group;
- and
- c is 1 or 2;
- to produce said bis-activated polyethylene glycol.
27 more elements
A process for preparing a bis-activated polyethylene glycol having the formula:
- Y-Q-O—(CH2—CH2—O)n-Q-Y
- wherein
- n is an integer between 4 and 800;
- Y is selected from the group consisting of a halide group, a mesyl group, a tosyl group, an imidazolyl group, an N-hydroxy-succinimidyl group, a phenoxyl group, and a substituted phenoxyl group;
- and
- Q is selected from the group consisting of SO2, CO(CHR1)tSO2, CO—O—(CHR1)t—O—SO2, C(O), SO2(CHR1)tSO2, SO2—O—(CHR1)t—O—SO2, CO—O—(CHR1)t—CR2═CR3—(CHR4)t—O—CO, and SO2—O—(CHR1)t—CR2═CR3—(CHR4)t—O—SO2,
- wherein
- t is 1, 2, or 3;
- and
- R1, R2, R3 and R4 are independently selected from the group consisting of H, a lower alkyl group, a lower branched alkyl group, an aryl group, and an aralkyl group;
- the process consisting essentially of reacting a polyethylene glycol having the formula:
- H—(O—CH2—CH2—)n—OH
- wherein
- n is an integer between 4 and 800;
- with an activator having the formula of Y-Q-X;
- wherein
- X and Y independently are selected from the group consisting of a halide group, a mesyl group, a tosyl group, an imidazolyl group, an N-hydroxy-succinimidyl group, a phenoxyl group, and a substituted phenoxyl group, provided that at least one of X and Y is a halide group;
- and
- Q is selected from the group consisting of SO2, CO(CHR1)tSO2, CO—O—(CHR1)t—O—SO2, C(O), SO2(CHR1)tSO2, SO2—O—(CHR1)t—O—SO2, CO—O—(CHR1)t—CR2═CR3—(CHR4)t—O—CO, and SO2—O—(CHR1)t—CR2═CR3—(CHR4)t—O—SO2,
- wherein
- t is 1, 2, or 3;
- and
- R1, R2, R3, and R4 are independently selected from the group consisting of H, a lower alkyl group, a lower branched alkyl group, an aryl group, and an aralkyl group;
- in the presence of a solvent and an aromatic nitrogen-containing heterocyclic base having the formula:
- wherein
- (NR5R6)c is located either in the ortho or para position;
- R5 and R6 are independently selected from the group consisting of a lower straight alkyl group, a lower branched alkyl group, an aryl group, and an aralkyl group;
- and
- c is 1 or 2;
- to produce said bis-activated polyethylene glycol.
27 more elements
A process for preparing a bis-activated polyethylene glycol having the formula:
- Y-Q-O—(CH2—CH2—O)n-Q-Y
- wherein
- n is an integer between 4 and 800;
- Y is selected from the group consisting of a halide group, a mesyl group, a tosyl group, an imidazolyl group, an N-hydroxy-succinimidyl group, a phenoxyl group, and a substituted phenoxyl group;
- and
- Q is selected from the group consisting of SO2, CO(CHR1)tSO2, CO—O—(CHR1)t—O—SO2, C(O), SO2(CHR1)tSO2, SO2—O—(CHR1)t—O—SO2, CO—O—(CHR1)t—CR2═CR3—(CHR4)t—O—CO, and SO2—O—(CHR1)t—CR2═CR3—(CHR4)t—O—SO2,
- wherein
- t is 1, 2, or 3;
- and
- R1, R2, R3 and R4 are independently selected from the group consisting of H, a lower alkyl group, a lower branched alkyl group, an aryl group, and an aralkyl group;
- the process consisting essentially of reacting a polyethylene glycol having the formula:
- H—(O—CH2—CH2—)n—OH
- wherein
- n is an integer between 4 and 800;
- with an activator having the formula of Y-Q-X;
- wherein
- X and Y independently are selected from the group consisting of a halide group, a mesyl group, a tosyl group, an imidazolyl group, an N-hydroxy-succinimidyl group, a phenoxyl group, and a substituted phenoxyl group;
- and
- Q is selected from the group consisting of SO2, CO(CHR1)tSO2, CO—O—(CHR1)t—O—SO2, C(O), SO2(CHR1)tSO2, SO2—O—(CHR1)t—O—SO2, CO—O—(CHR1)t—CR2═CR3—(CHR4)t—O—CO, and SO2—O—(CHR1)t—CR2═CR3—(CHR4)t—O—SO2,
- wherein
- t is 1, 2, or 3;
- and
- R1, R2, R3, and R4 are independently selected from the group consisting of H, a lower alkyl group, a lower branched alkyl group, an aryl group, and an aralkyl group;
- at a temperature range between about 20° C. and about 30° C., and in the presence of a solvent and an aromatic nitrogen-containing heterocyclic base having the formula:
- wherein
- (NR5R6)c is located either in the ortho or para position;
- R5 and R6 are independently selected from the group consisting of a lower straight alkyl group, a lower branched alkyl group, an aryl group, and an aralkyl group;
- and
- c is 1 or 2;
- to produce said bis-activated polyethylene glycol.
27 more elements
Dependencies are inferred from the claim text.