Sugar free, statistical copolymers made from at least three monomers

Patent metadata

Field	Value
Publication number	US-10030089-B2
Application number	US-201414889290-A
Country	US
Kind code	B2
Filing date	May 6, 2014
Priority date	May 6, 2013
Publication date	Jul 24, 2018
Grant date	Jul 24, 2018

Abstract

Disclosed herein are polymers made from at least three monomers of formulae (I), (II), (III), and (IV) that may be used in pharmaceutical formulations. These polymers comprise a hydrocarbon backbone and are made from monomers that contain at least one carbon-carbon double bond. Methods of making the polymers are also disclosed.

First claim

What is claimed is:

1. A polymer having a backbone formed by reacting acrylate monomers with a free radical initiator in the presence of a chain transfer agent, wherein the polymer backbone consists of monomeric units derived from a monomer of formula I, a monomer of formula II, a monomer of formula III, and a monomer of formula IV, wherein formulae I-IV are:

wherein
at each occurrence, R 1 , R 2 and R 3 are independently H or methyl;
R 4 is H or C 1 -C 6 alkyl;
R 6 is C 1 -C 6 alkyl; and,
the monomer of formula I is present in the backbone at a mole percent of from about 40-80;
the monomer of formula II is present in the backbone at a mole percent of from about 5-20;
the monomer of formula III is present in the backbone at a mole percent of from about 5-20;
the monomer of formula IV is present in the backbone at a mole percent of from about 5-35.

2. A polymer according to claim 1 , wherein at least one occurrence of R 1 is H.

3. A polymer according to claim 1 , wherein at least one occurrence of R 2 is H.

4. A polymer according to claim 1 , wherein at least one occurrence of R 3 is H.

5. A polymer according to claim 1 , wherein R 6 is C 1 -C 4 alkyl.

6. A polymer according to claim 1 , wherein the monomer of formula (I) has the formula:

7. A polymer according to claim 1 , wherein the monomer of formula (II) has the formula:

8. A polymer according to claim 1 , wherein the monomer of formula (III) has the formula:

or combinations thereof.

9. A polymer according to claim 1 , wherein the monomer of formula (IV) has the formula:

or combinations thereof.

10. A polymer according to claim 1 , wherein the polymer is a statistical polymer.

11. A method of making the polymer of claim 1 , comprising treating the at least three monomers, with a free radical initiator in the presence of a chain transfer agent.

12. A method according to claim 11 , wherein the free radical initiator is AIBN.

13. A pharmaceutical formulation comprising the polymer of claim 1 , and at least one active pharmaceutical ingredient.

14. A method of increasing the solubility of a drug, the method comprising formulating the drug with the polymer of claim 1 .

15. A polymer according to claim 1 , wherein the mole percent of monomers of formula I in the polymer backbone is from about 43 to about 75.

16. A polymer according to claim 1 , wherein the mole percent of monomers of formula IV in the polymer backbone is from about 7 to about 30.

17. A polymer according to claim 1 , wherein the mole percent of monomers of formula I in the polymer backbone is from about 43 to about 75, and the mole percent of monomers of formula IV in the polymer backbone is from about 7 to about 30.

Assignees

• Univ Minnesota
• The Regents Of The Univ Of Minnesota

Inventors

• Navale Tushar S
• Ting Jeffrey M
• Bates Frank S
• Reineke Theresa M

Classifications

• C08F220/281

  and containing only one oxygen, e.g. furfuryl (meth)acrylate or 2-methoxyethyl (meth)acrylate · CPC title

• C08F220/28 Primary

  containing no aromatic rings in the alcohol moiety · CPC title

• A61K47/32

  Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers {, poly(meth)acrylates, or polyvinyl pyrrolidone} · CPC title

• C08F2220/281

  Chemistry & Metallurgy · mapped topic

• C08F220/283

  and containing one or more carboxylic moiety in the chain, e.g. acetoacetoxyethyl(meth)acrylate · CPC title