Poly(ester amide) block copolymers

• US 7,699,889 B2
• Filed: 05/02/2008
• Issued: 04/20/2010
• Est. Priority Date: 12/27/2004
• Status: Expired due to Fees

• Current Assignee: Abbott Cardiovascular Systems Incorporated (Abbott Laboratories)
• Original Assignee: Advanced Cardiovascular Systems Incorporated (Abbott Laboratories)
• Inventors: Hossainy, Syed Faiyaz Ahmed
• Primary Examiner(s): WOODWARD, ANA LUCRECIA
• Application Number:
  US12/114,645
• Publication Number:
  US 20080206306A1
• Time in Patent Office: 718 Days
• Field of Search: 424/78.08, 424/78.3, 424/422, 424/423, 424/425, 424/457, 424/451, 424/489, 424/490, 623/1.15, 623/1.42, 623/1.46, 606/1
• US Class Current: 623/1.42
• CPC Class Codes: A61K 47/593 Polyesters, e.g. PLGA or polylactide-co-glycolide
• CPC Class Codes: A61K 47/595 Polyamides, e.g. nylon polyamino acids A61K47/62
• CPC Class Codes: A61K 47/64 Drug-peptide, drug-protein or drug-polyamino acid conjugates, i.e. the modifying agent being a peptide, protein or polyamino acid which is covalently bonded or complexed to a therapeutically active agent peptidic linkers A61K47/65
• CPC Class Codes: A61L 27/34 Macromolecular materials
• CPC Class Codes: A61L 31/10 Macromolecular materials
• CPC Class Codes: C08G 69/44 Polyester-amides
• CPC Class Codes: C08L 77/12 Polyester-amides

Abstract

Provided herein is a copolymer that includes a soft block (A) and a hard block (B) comprising a tyrosine di-peptide. The copolymer can be any of AB, ABA or BAB type block copolymers. The soft block can include a PEA polymer. A coating formed of the copolymer may also include a bioactive agent. The implantable device can be implanted in a patient to treat, prevent, or ameliorate a disorder such as atherosclerosis, thrombosis, restenosis, hemorrhage, vascular dissection or perforation, vascular aneurysm, vulnerable plaque, chronic total occlusion, claudication, anastomotic proliferation for vein and artificial grafts, bile duct obstruction, ureter obstruction, and/or tumor obstruction.

Claims

1. A coating for an implantable device comprising a copolymer and a drug, wherein the copolymer comprises a soft block (A) and a hard block (B) comprising tyrosine di-peptide, wherein the soft block (A) has a glass transition temperature (T_g) lower than that of the hard block, and

wherein the soft block (A) comprises a poly(ester amide).

2. The coating of claim 1 wherein the drug is selected from the group consisting of paclitaxel, docetaxel, estradiol, nitric oxide donors, super oxide dismutases, super oxide dismutases mimics, 4-amino-2,2,6,6-tetramethylpiperidine-1-oxyl (4-amino-TEMPO), tacrolimus, dexamethasone, rapamycin, rapamycin derivatives, 40-O-(2-hydroxy)ethyl-rapamycin (everolimus), 40-O-(3-hydroxy)propyl-rapamycin, 40-O-[2-(2-hydroxy)ethoxy]ethyl-rapamycin, and 40-O-tetrazole-rapamycin, ABT-578, clobetasol, progenitor cell capturing antibody, prohealing drugs, prodrugs thereof, co-drugs thereof, and a combination thereof.

3. The coating of claim 1, wherein the tyrosine di-peptide has a structure of

4. A implantable device comprising a coating, the coating comprising a copolymer and a drug, wherein the copolymer comprises a soft block (A) and a hard block (B) comprising tyrosine di-peptide, wherein the soft block (A) has a glass transition temperature (T_g) lower than that of the hard block, and

wherein the soft block (A) comprises a poly(ester amide).

5. The implantable device of claim 4, wherein the drug is selected from the group consisting of paclitaxel, docetaxel, estradiol, nitric oxide donors, super oxide dismutases, super oxide dismutases mimics, 4-amino-2,2,6,6-tetramethylpiperidine-1-oxyl (4-amino-TEMPO), tacrolimus, dexamethasone, rapamycin, rapamycin derivatives, 40-O-(2-hydroxy)ethyl-rapamycin (everolimus), 40-O-(3-hydroxy)propyl-rapamycin, 40-O-[2-(2-hydroxy)ethoxy]ethyl-rapamycin, and 40-O-tetrazole-rapamycin, ABT-578, clobetasol, progenitor cell capturing antibody, prohealing drugs, prodrugs thereof, co-drugs thereof, and a combination thereof.

6. The implantable device of claim 5, which is a stent.

7. The implantable device of claim 4, which is a stent.

8. The implantable device of claim 4, wherein the tyrosine di-peptide has a structure of