# US 6,294,697 B1 · Discrete-length polyethylene glycols

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- Number: US 6,294,697 B1
- Document ID: US6294697B1
- Status: Granted
- Kind: B1
- Application number: 09/062,286
- Filed: 1998-04-17
- Granted: 2001-09-25
- Earliest claimed: 1995-10-19
- Assignees: University of Washington
- Inventors: D. Scott Wilbur; Pradip M. Pathare
- Web page: https://patentgrep.com/patent/US6294697B1

## CPC

- C08L 71/02: Polyalkylene oxides
- A61K 47/60: the organic macromolecular compound being a polyoxyalkylene oligomer, polymer or dendrimer, e.g. PEG, PPG, PEO or polyglycerol
- C08G 65/329: with organic compounds
- C08G 65/34: from hydroxy compounds or their metallic derivatives {(C08G65/26 takes precedence)}
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

The present invention provides discrete-length polyethylene glycol and polyethylene glycol containing compounds and methods for their preparation.

## Claims

### Claim 1

An oxyethylene-containing compound, comprising the reaction product of:
a) at least one discrete oxyethylene-containing crosslinking moiety, wherein said crosslinking moiety comprises at least two reactive groups; and
b) at least two oxyethylene-containing moieties, wherein said oxyethylene-containing moieties are discrete and have a molecular weight of less than about 300 g/mol, the oxyethylene-containing moieties being covalently coupled to the crosslinking moiety through a bond selected from the group consisting of an amide bond, an ester bond, an amine bond, and combinations thereof.

### Claim 2 (depends on 1)

The compound of claim 1, wherein the oxyethylene-containing moiety comprises a radical selected from the group consisting of
radicals, wherein n=1-3.

### Claim 3 (depends on 1)

The compound of claim 1, wherein the oxyethylene-containing moiety comprises a 4,7,10-trioxa- 1,13-tridecane diamine radical.

### Claim 4 (depends on 1)

The compound of claim 1, wherein the oxyethylene-containing moiety comprises a 3,6,9-trioxaundecanedioic acid radical.

### Claim 5 (depends on 1)

The compound of claim 1, wherein the oxyethylene-containing moiety comprises a radical selected from the group consisting of
radicals, wherein n=0-2.

### Claim 6

The oxyethylene-containing compound

### Claim 7 (depends on 1)

The compound of claim 1 wherein the crosslinking moiety is selected from the group consisting of bifunctional and trifunctional crosslinking moieties.

### Claim 8 (depends on 1)

The compound of claim 1, wherein the crosslinking moiety comprises an alkyl moiety having a displaceable leaving group.

### Claim 9 (depends on 1)

The compound of claim 1, wherein the crosslinking moiety comprises a carboxylic acid group.

### Claim 10 (depends on 1)

The compound of claim 1, wherein the crosslinking moiety is radical a selected from the group consisting of
wherein n=0-3.

### Claim 11

A compound, comprising a first component coupled to an oxyethylene-containing linker through a first covalent bond, wherein the oxyethylene-containing linker comprises the reaction product of:
a) at least one discrete oxyethylene-containing crosslinking moiety, wherein said crosslinking moiety comprises at least two reactive groups, and
b) at least two oxyethylene-containing moieties, wherein said oxyethylene-containing moieties are discrete and have a molecular weight of less than about 300 g/mol, the oxyethylene-containing moieties being, covalently coupled to the crosslinking moiety through a bond selected from the group consisting of an amide bond, an ester bond, an amine bond, and combinations thereof.

### Claim 12 (depends on 11)

The compound of claim 11, wherein the first component has low solubility in an aqueous environment.

### Claim 13 (depends on 11)

The compound of claim 11, wherein the first component is a biologically active molecule.

### Claim 14 (depends on 11)

The compound of claim 11, wherein the first component is a therapeutic agent.

### Claim 15 (depends on 14)

The compound of claim 14, wherein the therapeutic agent is selected from the group consisting of a ubiquinone and derivatives thereof.

### Claim 16 (depends on 15)

The compound of claim 15, wherein the ubiquinone is ubiquinone 50.

### Claim 17 (depends on 14)

The compound of claim 14, wherein the therapeutic agent is selected from the group consisting of vitamin B12 and derivatives thereof.

### Claim 18 (depends on 11)

The compound of claim 11, wherein the first covalent bond is cleavable in vivo.

### Claim 19 (depends on 14)

A pharmaceutical composition, comprising the compound of claim 14 and a pharmaceutically acceptable carrier.

### Claim 20

A method for preparing, an oxyethylene-linked compound, comprising:
reacting a crosslinking agent with an oxyethylene-containing compound to form an oxyethylene linker having a first covalent bond between the crosslinking agent and the oxyethylene-containing compound, wherein the oxyethylene-containing compound is discrete and has a molecular weight of less than about 300g/mol, and wherein the first covalent bond is selected from the group consisting of an amide bond, an ester bond, and an amine bond; and
reacting the oxyethylene linker with a first component to form a second covalent bond between the oxyethylenelinker and the first component.

### Claim 21

A method for preparing an oxyethylene-containing compound, comprising:
reacting a first crosslinking agent with a first oxyethylene-containing compound to form a second oxyethylene-containing compound having a first covalent bond between the first crosslinking agent and the first oxyethylene-containing, compound, wherein the first oxyethylene-containing compound is discrete and has a molecular weight of less than about 300 g/mol, and wherein the first covalent bond is selected from the group consisting of an amide bond, an ester bond, and an amine bond; and
reacting the second oxyethylene-containing compound with a second crosslinking agent to form a second covalent bond between the second crosslinking agent and second oxyethylene-containing compound to form the oxyethylene-containing compound.

### Claim 22 (depends on 21)

The method of claim 21, further comprising reacting the oxyethylene-containing compound with a first component to form a covalent bond between the oxyethylene-containing compound and the first component.

### Claim 23 (depends on 21)

The method of claim 21, wherein the first and second crosslinking agents are the same.

### Claim 24 (depends on 20)

The method of claim 20, wherein the oxyethylene containing compound a radical selected from the group consisting of
radicals, wherein n=1-3.

### Claim 25 (depends on 20)

The method of claim 20, wherein the oxyethylene containing compound comprises a 4,7,10-trioxa-1,13-tridecane diamine radical.

### Claim 26 (depends on 20)

The method of claim 20, wherein the oxyethylene-containing compound comprises a 3,6,9-trioxaundecanedioic acid radical.

### Claim 27 (depends on 20)

The method of claim 20, wherein the oxyethylene-containing compound comprises a radical selected from the group consisting of
radicals, wherein n=0-2.

### Claim 28 (depends on 20)

The method of claim 20, wherein the crosslinking agent is selected from the group consisting of
wherein n=0-3, and R is a leaving group.

### Claim 29 (depends on 21)

The method of claim 21, wherein the oxyethylene moiety comprises a radical selected from the group consisting of
radicals, wherein n=1-3.

### Claim 30 (depends on 21)

The method of claim 21, wherein the oxyethylene moiety comprises a 4,7,10-trioxa-1,13-tridecane diamine radical.

### Claim 31 (depends on 21)

The method claim 21, wherein the oxyethylene moiety comprises a 3,6,9-trioxaundecanedioic acid radical.

### Claim 32 (depends on 21)

The method of claim 21, wherein the oxyethylene moiety comprises a radical selected from the group consisting of
radicals, wherein n=0-2.

### Claim 33 (depends on 21)

The method of claim 21, wherein the crosslinking agent is selected from the group consisting of
wherein n=0-3, and R is a leaving group.

### Claim 34

An oxyethylene-containing compound, comprising the reaction product of:
a) at least one discrete oxyethylene-containing crosslinking moiety, wherein said crosslinking moiety comprises at least two reactive groups; and
b) at least two oxyethylene-containing moieties, wherein said oxyethylene-containing moieties are discrete, the oxyethylene-containing moieties being covalently coupled to the crosslinking moiety through a bond selected from the group consisting of an amide bond an ester bond an amine bond and combinations thereof.

### Claim 35

A compound, comprising a first component coupled to an oxyethylene-containing linker through a first covalent bond, wherein the oxyethylene-containing linker comprises the reaction product of:
a) at least one discrete oxyethylene-containing crosslinking moiety wherein said crosslinking moiety comprises at least two reactive groups, and
b) at least two oxyethylene-containing moieties, wherein said oxyethylene-containing moieties are discrete, the oxyethylene-containing moieties being covalently coupled to the crosslinking moiety through a bond selected from the group consisting of an amide bond an ester bond, an amine bond, and combinations thereof.

### Claim 36

A method for preparing an oxyethylene-linked compound, comprising:
reacting a crosslinking agent with an oxyethylene-containing compound to form an oxyethylene linker having a first covalent bond between the crosslinking agent and the oxyethylene-containing compound, wherein the oxyethylene-containing compound is discrete, and wherein the first covalent bond is selected from the group consisting of an amide bond, an ester bond, and an amine bond; and
reacting the oxyethylene linker with a first component to form a second covalent bond between the oxyethylene linker and the first component.

### Claim 37

A method for preparing an oxyethylene-containing compound, comprising:
reacting a first crosslinking agent with a first oxyethylene-containing compound to form a second oxyethylene-containing compound having a first covalent bond between the first crosslinking agent and the first oxyethylene-containing compound, wherein the first oxyethylene-containing compound is discrete, and wherein the first covalent bond is selected from the group consisting of an amide bond, an ester bond, and an amine bond; and
reacting the second oxyethylene-containing compound with a second crosslinking agent to form a second covalent bond between the second crosslinking agent and second oxyethylene-containing compound to form the oxyethylene-containing compound.

### Claim 38 (depends on 37)

The method of claim 37, further comprising reacting the oxyethylene-containing compound with a first component to form a covalent bond between the oxyethylene-containing compound and the first component.