Aqueous polyglycidol synthesis with ultra-low branching

Patent metadata

Field	Value
Publication number	US-10308763-B2
Application number	US-201715684638-A
Country	US
Kind code	B2
Filing date	Aug 23, 2017
Priority date	Jan 24, 2014
Publication date	Jun 4, 2019
Grant date	Jun 4, 2019

Abstract

Disclosed herein are glycidol-based polymers, nanoparticles, and methods related thereto useful for a variety of applications, including, but not limited to, 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.

First claim

What is claimed is:

1. A polymer comprising repeating units selected from

and repeating units selected from

wherein R 0 is selected from H, alkyl, NH 2 , and R 1 ;
wherein R 1 comprises a crosslinking functionality;
wherein repeating units A1, A2, B1, and B2 account for at least about 50 wgt % of the polymer;
wherein the ratio of (A1+A2):(B1+B2) is greater than 1; and
wherein the polymer does not comprise a

 moiety; and
wherein the polymer is crosslinked.

2. The polymer of claim 1 , wherein the polymer comprises 0 wgt % of a repeating unit formed from tetrahydrofuran.

3. The polymer of claim 1 , wherein the ratio of (A1+A2):(B1+B2) is from about 1.5 to about 10.0.

4. A polymer comprising repeating units selected from

and repeating units selected from

wherein R 0 is selected from H, alkyl, NH 2 , and R 1 ;
wherein R 1 comprises a crosslinking functionality;
wherein repeating units A1, A2, B1, and B2 account for at least about 50 wgt % of the polymer;
wherein the ratio of (A1+A2):(B1+B2) is greater than 1; and
wherein the polymer does not comprise a

 moiety; and
wherein repeating units A1, A2, B1 and B2 account for at least about 100 wgt% of the polymer.

5. The polymer of claim 1 , wherein the polymer further comprises at least one repeating unit formed from a monomer selected from:

or a combination thereof.

6. The polymer of claim 1 , wherein the polymer has a weight average molecular weight from about 0.3 kDa to about 40 kDa.

7. A polymer comprising repeating units selected from

and repeating units selected from

wherein R 0 is selected from H, alkyl, NH 2 , and R 1 ;
wherein R 1 comprises a crosslinking functionality;
wherein repeating units A1, A2, B1, and B2 account for at least about 50 wgt % of the polymer;
wherein the ratio of (A1+A2):(B1+B2) is greater than 1; and
wherein the polymer does not comprise a

 moiety; and
wherein the polymer does not comprise a unit or repeating unit formed from diglycidyl ether.

8. A polymer comprising repeating units selected from

and repeating units selected from

wherein R 0 is selected from H, alkyl, NH 2 , and R 1 ;
wherein R 1 comprises a crosslinking functionality;
wherein repeating units A1, A2, B1, and B2 account for at least about 50 wgt % of the polymer;
wherein the ratio of (A1+A2):(B1+B2) is greater than 1; and
wherein the polymer does not comprise a

 moiety, and
wherein the polymer does not comprise an initiator other than glycidol.

9. The polymer of claim 1 , wherein the polymer does not comprise a metal catalyst residue.

10. The polymer of claim 9 , wherein the metal catalyst residue is a tin catalyst residue.

11. The polymer of claim 1 , wherein the degree of branching is between 0.15 and 0.30.

12. The polymer of claim 1 , wherein the degree of branching is between 0.20 and 0.30.

13. The polymer of claim 1 , wherein the polymer is further conjugated to a protein.

14. The polymer of claim 13 , wherein the protein is albumin.

15. The polymer of claim 1 , wherein the polymer includes crosslinkers that comprise

wherein at least one of

is not 0.

16. The polymer of claim 1 , wherein the polymer comprises

17. A pharmaceutical composition comprising a polymer of claim 1 and a pharmaceutically acceptable carrier.

18. The pharmaceutical composition of claim 17 , wherein the pharmaceutical composition further comprises a pharmaceutically active agent or a biologically active agent.

19. A nanoparticle comprising a polymer of claim 1 .

Assignees

• Univ Vanderbilt

Inventors

• Harth Eva M
• Spears Benjamin R

Classifications

• C08G2650/24

  Polymeric initiators · CPC title

• C08G65/34 Primary

  from hydroxy compounds or their metallic derivatives {(C08G65/26 takes precedence)} · CPC title

• C08G2650/56

  Polyhydroxyethers, e.g. phenoxy resins · CPC title

• C08G65/22 Primary

  Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring · CPC title

• C08G2650/38

  containing oxygen in addition to the ether group · CPC title