# US 11,305,018 B2 · Linear polyester and semi-linear glycidol polymer systems: formulation and synthesis of novel monomers and macromolecular structures

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- Number: US 11,305,018 B2
- Document ID: US11305018B2
- Status: Granted
- Kind: B2
- Application number: 16/801,014
- Filed: 2020-02-25
- Published: 2020-07-30
- Granted: 2022-04-19
- Earliest claimed: 2012-06-15
- Assignees: Vanderbilt University
- Applicants: Vanderbilt University
- Inventors: Eva M. Harth; Dain B. Beezer; GuangZhao Li; Benjamin R. Spears; David M. Stevens
- Web page: https://patentgrep.com/patent/US11305018B2

## CPC

- A61K 47/34: Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers (A61K47/10 takes precedence)
- A61K 9/0019: {Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner (non-active ingredients are additionally classified in A61K47/00)}
- A61K 9/5031: {obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, poly(lactide-co-glycolide)}
- A61K 47/32: Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers {, poly(meth)acrylates, or polyvinyl pyrrolidone}
- C08G 64/42: Chemical after-treatment
- C08G 65/00: Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G 65/002: {from unsaturated compounds (unsaturated oxiranes C08G65/14)}
- C08G 65/22: Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
- C08G 65/2615: {the other compounds containing carboxylic acid, ester or anhydride groups}
- C08G 65/3326: {aromatic}
- C08G 65/3348: {containing nitrogen in addition to sulfur}
- C08G 65/34: from hydroxy compounds or their metallic derivatives {(C08G65/26 takes precedence)}
- 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

Disclosed herein are glycidol-based polymers, nanoparticles, and methods related thereto useful for drug delivery. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

## Claims

### Claim 1

A method for making a polymer, the method comprising polymerizing glycidol to form the polymer, the polymer comprising repeating units selected from:
wherein R0 is selected from H, alkyl, NH2, and R1;
wherein R1 comprises a crosslinking functionality; and
wherein the ratio of (A1+A2):(B1+B2) is greater than 5.

### Claim 2 (depends on 1)

The method of claim 1, wherein polymerizing glycidol is performed at a temperature ranging from −80° C. to 50° C.

### Claim 3 (depends on 1)

The method of claim 1, further comprising crosslinking the polymer with crosslinks.

### Claim 4 (depends on 3)

The method of claim 3, wherein the crosslinks comprise one or more of
wherein at least one of
is not 0.

### Claim 5 (depends on 1)

The method of claim 1, wherein the ratio of (A1+A2):(B1+B2) is greater than 10.

### Claim 6

A method for making a polymer, the method comprising polymerizing glycidol to form the polymer, the polymer comprising at least one repeating unit formed from a monomer selected from:
or a combination thereof.

### Claim 7 (depends on 6)

The method of claim 6, wherein polymerizing glycidol is performed at a temperature ranging from −80° C. to 50° C.

### Claim 8 (depends on 6)

The method of claim 6, further comprising crosslinking the polymer with crosslinks.

### Claim 9 (depends on 8)

The method of claim 8, wherein the crosslinks comprise one or more of:
wherein at least one of
is not 0.

### Claim 10

A method of forming a nanoparticle comprising:
polymerizing glycidol to form a polymer, the polymer comprising at least one repeating unit formed from a monomer selected from:
or a combination thereof; and
crosslinking the polymer with crosslinks, wherein the crosslinks comprise:
wherein at least one of
is not 0, thereby forming the nanoparticle.

### Claim 11 (depends on 10)

The method of claim 10, wherein polymerizing glycidol is performed at a temperature ranging from −80° C. to 50° C.