N-substituted monomers and polymers

• US 8,288,590 B2
• Filed: 07/14/2011
• Issued: 10/16/2012
• Est. Priority Date: 10/17/2006
• Status: Expired due to Fees

• Current Assignee: Rutgers University
• Original Assignee: Rutgers University
• Inventors: Kohn, Joachim B., Bolikal, Durgadas, Schut, Jaap, Baluca, Ernest G.
• Primary Examiner(s): WITHERSPOON, SIKARL A
• Application Number:
  US13/183,051
• Publication Number:
  US 20110269848A1
• Time in Patent Office: 460 Days
• Field of Search: 564/170, 568/774, 514/772.3, 525/408, 528/172, 528/203, 528/208
• US Class Current: 564/170
• CPC Class Codes: A61L 2300/00 Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
• CPC Class Codes: A61L 31/06 obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds A61L31/041 takes precedence
• CPC Class Codes: A61L 31/10 Macromolecular materials
• CPC Class Codes: A61L 31/16 Biologically active materials, e.g. therapeutic substances A61L31/047 takes precedence
• CPC Class Codes: B33Y 80/00 Products made by additive manufacturing
• CPC Class Codes: C08G 63/6856 Dicarboxylic acids and dihydroxy compounds
• CPC Class Codes: C08G 64/045 containing aliphatic unsaturation
• CPC Class Codes: C08G 64/12 containing nitrogen
• CPC Class Codes: C08G 64/183 containing polyether sequences
• CPC Class Codes: C08G 64/186 containing polysiloxane sequences
• CPC Class Codes: C08G 79/04 Phosphorus linked to oxygen or to oxygen and carbon
• CPC Class Codes: C08L 69/00 Compositions of polycarbonates; Compositions of derivatives of polycarbonates
• CPC Class Codes: C08L 85/02 containing phosphorus

Abstract

Biocompatible, bioresorbable polymers comprising a plurality of monomeric repeating units containing an amide group, wherein said amide groups are N-substituted and the N-substituent and degree of N-substitution are effective to lower the melt viscosity, the solution viscosity, or both, compared to the same polymer without N-substitution.

Claims

1. A blood-contacting or tissue-implantable medical device formed from a biocompatible, bioresorbable polymer comprising a plurality of monomeric repeating units containing an amide group, wherein said amide groups comprise N-substituted amide groups and the N-substituents and degree of N-substitution are effective to lower the melt viscosity of said polymer, the solution viscosity of said polymer, or both, compared to the same polymer without N-substitution.

2. The medical device according to claim 1, wherein said N-substituents and degree of N-substitution are effective to reduce the melt viscosity of said polymer, the solution viscosity of said polymer, or both, at least about 5%.

3. The medical device according to claim 1, wherein said N-substituents of said polymer comprise C₁-C₆ alkyl groups.

4. A biocompatible, bioresorbable polymer comprising one or more recurring units of the formula:

6. The polymer of claim 4, wherein R¹ contains between about 18 and about 36 carbon atoms.

9. The polymer according to claim 4, wherein at least one monomeric aromatic ring of formula (I) is substituted with iodine, so that the sum of y1 and y2 in formula (I) is greater than zero.

12. A polymer according to claim 4, characterized by being a polycarbonate, polyarylate, polyiminocarbonate, polyphosphazene or polyphosphoester, comprising one or more recurring units having the structure of formula (Ia),

13. The polymer according to claim 4, further comprising recurring polyalkylene oxide block units comprising repeating units with the structure:

16. A polymer according to claim 12, further comprising recurring polyalkylene oxide block units comprising repeating units with the structure:

17. The polymer of claim 12, characterized by being a copolymer of a diphenol monomer that is not N-substituted.

20. The polymer according to claim 12, wherein at least one monomeric aromatic ring of formula (I) is substituted with iodine, so that the sum of y1 and y2 in formula (I) is greater than zero.

5. A biocompatible, bioresorbable polymer comprising one or more recurring units of the formula:

18. The polymer according to claim 5, wherein at least one monomeric aromatic ring of formula (I) is substituted with iodine, so that the sum of y1 and y2 in formula (I) is greater than zero.

22. The polymer according to claim 5, further comprising recurring polyalkylene oxide block units comprising repeating units with the structure:

25. The polymer of claim 5, characterized by being a copolymer of a diphenol monomer that is not N-substituted.

7. A biocompatible, bioresorbable polymer comprising one or more recurring units of the formula:

8. The polymer according to claim 7, wherein R⁸ is an alkyl-terminated poly(alkylene oxide) selected from the group consisting of methoxy-terminated poly(ethylene glycols) (PEG) of molecular weight 100 to 10,000, methoxy-terminated poly(propylene glycols) (PPG) of molecular weight 100 to 10,000 and methoxy-terminated block copolymers of PEG and PPG of molecular weight 100 to 10,000.

10. The polymer according to claim 7, wherein R⁸ is OH.

11. The polymer according to claim 7, wherein R¹ is selected from:

19. The polymer according to claim 7, wherein at least one monomeric aromatic ring of formula (I) is substituted with iodine, so that the sum of y1 and y2 in formula (I) is greater than zero.

23. The polymer according to claim 7, further comprising recurring polyalkylene oxide block units comprising repeating units with the structure:

26. The polymer of claim 7, characterized by being a copolymer of a diphenol monomer that is not N-substituted.

14. A biocompatible, bioresorbable polymer comprising one or more recurring units of the formula:

21. The polymer according to claim 14, wherein at least one monomeric aromatic ring of formula (I) is substituted with iodine, so that the sum of y1 and y2 in formula (I) is greater than zero.

24. The polymer according to claim 14, further comprising recurring polyalkylene oxide block units comprising repeating units with the structure:

15. An implantable drug delivery device comprising a therapeutically effective amount of a biologically or a physiologically active compound in combination with a biocompatible, bioresorbable polymer comprising a plurality of monomeric repeating units containing an amide group, wherein the amide groups comprise N-substituted amide groups and the N-substituents and degree of N-substitution are effective to lower the melt viscosity of said polymer, the solution viscosity of said polymer, or both, compared to the same polymer without N-substitution.