Radio-opaque polymer biomaterials

• US 20040086462A1
• Filed: 10/23/2003
• Published: 05/06/2004
• Est. Priority Date: 11/07/1997
• Status: Abandoned Application

• Current Assignee: Rutgers University - Department of Chemistry
• Original Assignee: Rutgers University - Department of Chemistry
• Inventors: Pendharkar, Sanyog M., Bolikal, Durgadas, Kohn, Joachim B.
• Application Number:
  US10/692,122
• Publication Number:
  US 20040086462A1
• Time in Patent Office: Days
• US Class Current: 424/9.451
• CPC Class Codes: A61K 38/00 Medicinal preparations containing peptides peptides containing beta-lactam rings A61K31/00; cyclic dipeptides not having in their molecule any other peptide link than those which form their ring, e.g. piperazine-2,5-diones, A61K31/00; ergot alkaloids of the cyclic peptide type A61K31/48; containing macromolecular compounds having statistically distributed amino acid units A61K31/74; medicinal preparations containing antigens or antibodies A61K39/00; medicinal preparations characterised by the non-active ingredients, e.g. peptides as drug carriers, A61K47/00
• CPC Class Codes: A61K 49/0438 Organic X-ray contrast-enhancing agent comprising an iodinated group or an iodine atom, e.g. iopamidol
• CPC Class Codes: A61K 49/0442 Polymeric X-ray contrast-enhancing agent comprising a halogenated group
• CPC Class Codes: A61K 49/0447 Physical forms of mixtures of two different X-ray contrast-enhancing agents, containing at least one X-ray contrast-enhancing agent which is a halogenated organic compound
• CPC Class Codes: A61K 9/204 Polyesters, e.g. poly(lactide-co-glycolide)
• CPC Class Codes: A61L 2300/00 Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
• 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: A61L 31/18 Materials at least partially X-ray or laser opaque
• CPC Class Codes: C08G 63/672 Dicarboxylic acids and dihydroxy compounds
• CPC Class Codes: C08G 63/6826 Dicarboxylic acids and dihydroxy compounds
• CPC Class Codes: C08G 63/6856 Dicarboxylic acids and dihydroxy compounds
• CPC Class Codes: C08G 64/10 containing halogens
• CPC Class Codes: C08G 64/12 containing nitrogen
• CPC Class Codes: C08G 64/1633 containing halogens
• CPC Class Codes: C08G 64/1641 containing nitrogen
• CPC Class Codes: C08G 64/183 containing polyether sequences
• CPC Class Codes: C08G 65/3317 phenolic
• CPC Class Codes: C08G 69/44 Polyester-amides
• CPC Class Codes: C08K 5/13 Phenols; Phenolates
• CPC Class Codes: C08K 5/20 : Carboxylic acid amides

Abstract

Iodinated and/or brominated derivatives of aromatic dihydroxy monomers are prepared and polymerized to form radio-opaque polymers. The monomers may also be copolymerized with other dihydroxy monomers. The iodinated and brominated aromatic dihydroxy monomers can be employed as radio-opacifying, biocompatible non-toxic additives for other polymeric biomaterials. Radio-opaque medical implants and drug delivery devices for implantation prepared from the polymers of the present invention are also disclosed.

Claims

1. An implantable, radio-opaque medical device comprising a radio-opaque, iodine- or bromine-containing polymer having at least one repeating unit derived from a monomer described by the formula (I):

2. The implantable, radio-opaque medical device of claim 1, wherein R₉ has the structure (II):

3. The implantable, radio-opaque medical device of claim 2, wherein R₄ is —

CH₂—

or —

CHJ₁—

CHJ₂— and

R₀ is —

CH₂—

or —

CH₂—

CH₂—

.

4. The implantable, radio-opaque medical device of claim 2, wherein Z is a free carboxylic acid group, or an ethyl, butyl, hexyl, octyl or benzyl ester or amide thereof.

5. The implantable, radio-opaque medical device of claim 1, wherein Y₁+Y₂ is greater than zero.

6. The implantable, radio-opaque medical device of claim 1 wherein said medical device is formed from said polymer.

7. The implantable, radio-opaque medical device of claim 1 wherein said medical device is coated with said polymer.

10. The implantable, radio-opaque medical device of claim 1, wherein said polymer further comprises one or more poly(alkylene oxide) blocks.

8. The implantable, radio-opaque medical device of 1 wherein said device comprises a radio-opaque, biocompatible stent comprising said polymer.

11. An implantable, radio-opaque medical device comprising a radio-opaque polymer having at least one repeating unit derived from a monomer described by the formula (III):

9. The implantable, radio-opaque medical device of claim 12 wherein said device is a radio-opaque, biocompatible stent.

12. The implantable, radio-opaque medical device of claim 11, wherein R₁₅ is —

CH₂—

or —

CHJ₁—

CHJ₂— and

R₀ is —

CH₂—

or —

CH₂—

CH₂—

.

13. The implantable, radio-opaque medical device of claim 11, wherein Z is a free carboxylic acid group or an ethyl, butyl, hexyl, octyl or benzyl ester or amide thereof.

14. The implantable, radio-opaque medical device of claim 11, wherein R₁₅ is (—

CH₂—

)_c, c is 0 and R₁ and R₂ are independently hydrogen or a methyl group.

15. The implantable, radio-opaque medical device of claim 14, wherein R₁ and R₂ are both hydrogen.

16. The implantable, radio-opaque medical device of claim 14, wherein one of R₁ and R₂ is hydrogen and the other is a methyl group.

17. The implantable, radio-opaque medical device of claim 11, wherein R₀ is —

CH₂— and

Z is a carboxylic acid ethyl ester.

18. The implantable, radio-opaque medical device of claim 11, wherein Y₂ is 1 or 2.

19. The implantable, radio-opaque medical device of claim 11, wherein said polymer further comprises one or more poly(alkylene oxide) blocks.

20. The implantable, radio-opaque medical device of claim 11 wherein said medical device is formed from said polymer.

21. The implantable, radio-opaque medical device of claim 11 wherein said medical device is coated with said polymer.

23. The implantable, radio-opaque medical device of claim 20 wherein said device is a radio-opaque, biocompatible stent.

22. The implantable, radio-opaque medical device of 11 wherein said device comprises a radio-opaque, biocompatible stent comprising said polymer.