Poly(ester amide) block copolymers

• US 7,419,504 B2
• Filed: 12/27/2004
• Issued: 09/02/2008
• Est. Priority Date: 12/27/2004
• Status: Expired due to Fees

• Current Assignee: Advanced Cardiovascular Systems Incorporated
• Original Assignee: Advanced Cardiovascular Systems Incorporated
• Inventors: Hossainy, Syed Faiyaz Ahmed
• Primary Examiner(s): WOODWARD, ANA LUCRECIA
• Application Number:
  US11/023,837
• Publication Number:
  US 20060142541A1
• Time in Patent Office: 1,345 Days
• Field of Search: 528/272, 528/271, 424/78.08, 424/423, 424/497, 424/451, 424/457, 424/489, 424/490, 424/78.3, 424/422, 623/1.46, 623/1.42, 623/1.15, 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) that contains poly(ester amide) (PEA) and a hard block (B). The copolymer can be any of AB, ABA or BAB type block copolymers. By varying the relative amount of the PEA block and the hard block, one can obtain a copolymer with a T_g for mechanical integrity in drug-delivery stent applications. The copolymer can be used alone or optionally in combination with a biobeneficial material and/or a biocompatible polymer to form an implantable device or a coating on an implantable device. When the copolymer is used in combination with a biobeneficial material, the copolymer and the biobeneficial material can be co-deposited or applied in sequence during the coating process. 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. An absorbable stent formed of a material comprising a copolymer,

wherein the copolymer comprises a soft block (A) that comprises poly(ester amide) (PEA) and a hard block (B), and

wherein the hard block comprises a block derived from tyrosine di-peptide and a polymer selected from the group consisting of poly(D,L-lactic acid-co-glycolic acid) (PDLLG), poly(glycerol-sebacic acid), polytyrosine carbonate, polytyrosine, tyrosine oligomer, poly(3-hydroxybutyrate) (PHB), poly(3-hydroxybutyrate-co-3-hydroxyvalerate) (PHBV), poly(3-hydroxyvalerate) (PHV), polyphosphazene, and combinations thereof.

2. An absorbable stent formed of a material comprising a copolymer, wherein the copolymer comprises a poly(ester amide) block and a tyrosine di-peptide block.

3. An absorbable stent formed of a material comprising a copolymer and drug, wherein the copolymer comprises a soft block (A) that comprises poly(ester amide) (PEA) and a hard block (B), and

wherein the hard block comprises a block derived from tyrosine di-peptide and a polymer selected from the group consisting of poly(D,L-lactic acid-co-glycolic acid) (PDLLG), polyglycerol-sebacic acid, polytyrosine carbonate, polytyrosine, tyrosine oligomer, poly(3-hydroxybutyrate) (PHB), poly(3-hydroxybutyrate-co-3-hydroxyvalerate) (PHBV), poly(3-hydroxyvalerate) (PHV), polyphosphazene, and combinations thereof.

4. An absorbable stent formed of a material comprising a copolymer and a drug, wherein the copolymer comprises a poly(ester amide) block and a tyrosine di-peptide block.