Polyesters and methods of use thereof

• US 9,144,579 B2
• Filed: 08/19/2013
• Issued: 09/29/2015
• Est. Priority Date: 08/17/2012
• Status: Active Grant

• Current Assignee: Rutgers University
• Original Assignee: Rutgers University
• Inventors: Uhrich, Kathryn E., Rosario-Melendez, Roselin
• Primary Examiner(s): GULLEDGE, BRIAN M
• Application Number:
  US13/970,220
• Publication Number:
  US 20140050692A1
• Time in Patent Office: 771 Days
• Field of Search: None
• US Class Current: 1/1
• CPC Class Codes: A61K 31/192 having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid cannabinoids A61K31/658
• CPC Class Codes: A61K 31/765 Polymers containing oxygen
• CPC Class Codes: A61K 31/775 Phenolic resins
• CPC Class Codes: A61K 47/593 Polyesters, e.g. PLGA or polylactide-co-glycolide
• CPC Class Codes: C08G 63/16 Dicarboxylic acids and dihydroxy compounds

Abstract

The invention provides polymers and methods for the treatment of pain and inflammation.

Claims

1. A polyester comprising one or more groups of formula (I):

—

C(═

O)-A-C(═

O)—

O-L-O—

 

 

(I)

wherein A is a C₂-C₈ methylene chain that is covalently linked to two or more residues of a non-steroidal anti-inflammatory; and

L is a C₂-C₁₀ branched or straight chain alkyl.

2. The polyester of claim 1, wherein the C₂-C₈ methylene chain that is covalently linked to two or more residues of the non-steroidal anti-inflammatory through an ester or amide linkage.

3. The polyester of claim 1 which comprises one or more groups of formula (Ia):

—

C(═

O)—

[CH(B)]_2-8—

C(═

O)—

O-L-O—

 

 

(Ia)

wherein each B is independently a residue of a non-steroidal anti-inflammatory.

4. A polyester according to claim 1, which comprises one or more groups of formula (II):

5. The polyester of claim 4 wherein D is —

O—

.

6. The polyester of claim 5 which comprises one or more groups of formula (IIa):

7. The polyester of claim 5 which comprises one or more groups of formula (IIb):

8. A polyester accordingly to claim 1, which comprises two or more repeating groups of formula (II):

9. The polyester of claim 8 which comprises 2-200 repeating groups of formula (II).

10. The polyester of claim 8 which comprises at least 2, 3, 4, 5, 6, 7, 8, or 9 repeating groups of formula (II).

11. The polyester of claim 8 which comprises two or more repeating groups of formula (IIa):

12. The polyester of claim 8 which comprises two or more repeating groups of formula (IIb):

13. The polyester of claim 1 wherein each non-steroidal anti-inflammatory agent is selected from ibuprofen, naproxen, fenoprofen, ketoprofen, flurbiprofen, suprofen, benoxaprofen, indoprofen, pirprofen, carprofen, loxoprofen, pranoprofen, alminoprofen, salicylic acid, diflunisal, salsalate, oxaprozin, indomethacin, sulindac, etodolac, ketorolac, diclofenac, piroxicam, meloxicam, tenoxican, lornoxicam, isoxicam, mefenamic acid, meclofenamic acid, flufenamic acid, tolfenamic acid, lumiracoxib and licofelone.

14. The polyester of claim 1, wherein L is a C₂-C₁₀ straight chain alkyl.

15. The polyester of claim 14, wherein L is a C₄-C₈ straight chain alkyl.

16. The polyester of claim 15, wherein L is a C₆ straight chain alkyl.

17. The polyester of claim 1, wherein L is a C₂-C₁₀ branched chain alkyl.

18. A pharmaceutical composition comprising a polyester as described in claim 1 and a pharmaceutically acceptable carrier.

19. A method to treat pain or inflammation in a mammal, comprising administering a polyester as described in claim 1 to the mammal.