IP Library Patent Application 11400935
Patent Application
App. No. 11/400,935

Functionalized poly(ethylene glycol)

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Patent No.
US None
App. No.
11/400,935
Abstract

The present invention relates to a bi-functional compound containing a linking material, and a particle comprising a linking material, and a linking material comprising a polyethylene glycol macromonomer backbone with a radical polymerizable group at one end of the macromonomer backbone and a different reactive chemical functionality at the other end of the macromonomer backbone, according to Formula I: wherein X is CH 3 , CN or H; Y is O, NR 1 , or S; L is a linking group or spacer; FG is a functional group; n is greater than 4 and less than 1000; and wherein R 1 and R 2 are independently selected from substituted or unsubstituted alkyl, aryl, or heteroyl.

Claims (46)

1 . A linking material comprising a polyethylene glycol macromonomer backbone with a radical polymerizable group at one end of said macromonomer backbone and a different reactive chemical functionality at the other end of said macromonomer backbone, according to Formula I:

wherein X is CH 3 , CN or H;

Y is O, NR 1 , or S;

L is a linking group or spacer;

FG is a functional group excluding alkoxy silanes;

n is greater than 4 and less than 1000; and

wherein R 1 is selected from substituted or unsubstituted alkyl, aryl, or heteroyl.

2 . The linking material of claim 1 wherein FG is selected from the group consisting of halogen, haloacetamides, hydroxy, active esters, thiols, benzotriazole carbonates, p-nitrophenylcarbonates, isocyanates, and isothiocyanates NH2, NHR 2 or COOH, wherein R 2 is independently selected from substituted or unsubstituted alkyl, aryl, or heteroyl.

3 . The linking material of claim 1 wherein FG is NH2, NHR 2 or COOH, wherein R 2 is independently selected from substituted or unsubstituted alkyl, aryl, or heteroyl.

4 . The linking material of claim 1 wherein FG is NH2 or COOH.

5 . The linking material of claim 1 wherein X is CH3.

6 . The linking material of claim 1 wherein Y is O or NR 1 .

7 . The linking material of claim 1 wherein L can be substituted or unsubstituted alkyl, alkyloxy, aryl or heteroyl.

8 . The linking material of claim 1 wherein L is branched.

9 . The linking material of claim 1 wherein n is between 10 and 200.

10 . The linking material of claim 1 wherein n is between 6 and 500.

11 . The linking material of claim 1 wherein n is 16.

12 . The linking material of claim 1 wherein R 1 and R 2 are independently selected from the group consisting of alkyloxy, alkylhdydroxy, alkylamino, alkylcarbonamido, alkylcarbamoyl, alkylthioether, alkylthioester, aryloxy, arylamino, arylcarbonamido, arylcarbamoyl, arylnitro, arylthioester, arylthioether, and arylcarboxyalkyl.

13 . The linking material of claim 1 wherein said polyethylene glycol macromonomer backbone has a molecular weight of from 300 to 10,000.

14 . The linking material of claim 1 wherein said polyethylene glycol of Formula I is represented by the following structure II:

15 . The linking material of claim 1 wherein said polyethylene glycol of Formula I is represented by the following structure III:

16 . The linking material of claim 1 wherein said polyethylene glycol of Formula I is represented by the following structure IV:

17 . The linking material of claim 1 wherein said radical polymerizable group at one end of said macromonomer backbone is capable of Michael addition.

18 . The linking material of claim 1 wherein FG is capable of alkylation or acylation.

19 . The linking material of claim 1 wherein said linking material is utilized in an aqueous physiological environment.

20 . A bi-functional compound comprising a single linking material comprising a polyethylene glycol macromonomer backbone with a single radical polymerizable group at one end of said macromonomer backbone and a different reactive chemical functionality FG at the other end of said macromonomer backbone, according to Formula I:

wherein X is CH 3 , CN or H;

Y is O, NR 1 , or S;

L is a linking group or spacer;

FG is alkylated or acylated to a second functional compound;

n is greater than 4 and less than 1000; and

wherein said single radical polymerizable group is reacted to a first functional compound;

FG is NH 2 , NHR 2 or COOH prior to alkylation or acylation to said second functional compound; and

wherein R 1 and R 2 are independently selected from substituted or unsubstituted alkyl, aryl, or heteroyl.

21 . The bi-functional compound of claim 20 wherein said first functional compound is a nanogel, a latex or a compound having a thiol group.

22 . The bi-functional compound of claim 20 wherein said second functional compound is at least one member selected from the groups consisting of contrast agents, dyes, proteins, amino acids, peptides, antibodies, bioligands, targeting agents, diagnostic agents, therapeutic agents and enzyme inhibitors.

23 . A carrier particle comprising a particle having attached thereto a plurality of linking compounds comprising a polyethylene glycol macromonomer backbone with a single radical polymerizable group at one end of said macromonomer backbone, wherein said radical polymerizable group is reacted to said particle, and a different reactive chemical functionality FG at the other end of said macromonomer backbone, according to Formula I:

wherein X is CH 3 , CN or H;

Y is O, NR 1 , or S;

L is a linking group or spacer;

FG is alkylated or acylated to a carried compound;

n is greater than 4 and less than 1000;

wherein FG is NH 2 , NHR 2 or COOH prior to said alkylation or acylation to said carried compound; and

wherein R 1 and R 2 are independently selected from substituted or unsubstituted alkyl, aryl, or heteroyl.

24 . The carrier particle of claim 23 wherein said particle is a nanogel, a latex, or a particle with thiol groups for reacting through Michael addition.

25 . The carrier particle of claim 23 wherein said carried compound is at least one member selected from the groups consisting of contrast agents, dyes, proteins, amino acids, peptides, antibodies, bioligands, targeting agents, diagnostic agents, therapeutic agents and enzyme inhibitors. t the

Assignments (6)
RELEASE OF SECURITY INTEREST IN INTELLECTUAL PROPERTY (FIRST LIEN) Recorded Apr 4, 2011
From: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH
To: CARESTREAM HEALTH, INC.
Reel/Frame 026069/0012 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 7, 2008
From: EASTMAN KODAK COMPANY
To: CARESTREAM HEALTH, INC.
Reel/Frame 020741/0126 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 7, 2008
From: EASTMAN KODAK COMPANY
To: CARESTREAM HEALTH, INC.
Reel/Frame 020756/0500 →
FIRST LIEN OF INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Jul 27, 2007
From: CARESTREAM HEALTH, INC.
To: CREDIT SUISSE, CAYMAN ISLANDS BRANCH, AS ADMINISTRATIVE AGENT
Reel/Frame 019649/0454 →
SECOND LIEN INTELLECTUAL PROPERTY SECURITY AGREEME Recorded Jul 27, 2007
From: CARESTREAM HEALTH, INC.
To: CREDIT SUISSE, CAYMAN ISLANDS BRANCH, AS ADMINISTRATIVE AGENT
Reel/Frame 019773/0319 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 10, 2006
From: HARDER, JOHN W.; LEON, JEFFREY W.
To: EASTMAN KODAK COMPANY
Reel/Frame 017774/0233 →