Biologically absorbable coatings for implantable devices based on polyesters and methods for fabricating the same
First Claim
Patent Images
1. A composition comprising a polymer represented by a formula:
1 Assignment
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Accused Products
Abstract
Polymers containing polyesters and, optionally, agents for use with medical articles and methods of fabricating the same are disclosed. The medical article generally comprises an implantable substrate having a coating, and the coating contains a polymer comprising a polymeric product of a reaction comprising a polyol and a polycarboxylic acid.
355 Citations
69 Claims
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1. A composition comprising a polymer represented by a formula:
- View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69)
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2. The composition of claim 1, wherein R1 or R3 comprise an aromatic radical.
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3. The composition of claim 2, wherein the aromatic radical comprises a component selected from the group consisting of p-phenylene, m-phenylene, o-phenylene, and derivatives thereof.
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4. The composition of claim 1, wherein
R1 comprises a phenylene radical or a derivative thereof; -
R2 and R4 each comprises a component independently selected from a group consisting of 1,3-propanediol, 1,4-butanediol, 1,6-hexanediol, and derivatives thereof; and R3 comprises a component selected from a group consisting of adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, and derivatives thereof.
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5. The composition of claim 1, wherein the agent comprises a component selected from a group consisting of poly(ethylene glycol), poly(propylene glycol), poly(N-vinyl pyrrolidone), phosphorylcholine, glycosaminoglycans, carboxymethylcellulose, hyaluronic acid, heparin, hirudin, poly(acrylamide methyl propane sulfonic acid), poly(styrene sulfonate), sulfonated dextran, dermatan sulfate, RGD, collagen, chitin, chitosan, elastin and any derivatives, analogs, homologues, congeners, salts, copolymers and combinations thereof.
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6. The composition of claim 1, wherein the agent comprises poly(ethylene glycol), poly(N-vinyl pyrrolidone), phosphorylcholine, hyaluronic acid, heparin, hirudin, or any derivatives, analogs, homologues, congeners, salts, copolymers or combinations thereof.
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7. The composition of claim 1, wherein the agent comprises a component selected from a group consisting of a free radical scavenger, a nitric oxide donor, rapamycin, everolimus, tacrolimus, paclitaxel, docetaxel, estradiol, clobetasol, idoxifen, tazarotene and any prodrugs, metabolites, analogs, homologues, congeners, and any derivatives, salts and combinations thereof.
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8. The composition of claim 7, wherein the free radical scavenger comprises a component selected from a group consisting of 2,2′
- ,6,6′
-tetramethyl-1-piperinyloxy, free radical;
4-amino-2,2′
,6,6′
-tetramethyl-1-piperinyloxy, free radical;
4-hydroxy-2,2′
,6,6′
-tetramethyl-piperidene-1-oxy, free radical;
2,2′
,3,4,5,5′
-hexamethyl-3-imidazolinium-1-yloxy methyl sulfate, free radical;
16-doxyl-stearic acid, free radical;
superoxide dismutase mimic; and
, any analogs, homologues, congeners, derivatives, salts and combinations thereof.
- ,6,6′
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9. The composition of claim 7, wherein the free radical scavenger comprises TEMPO or any analogs, homologues, congeners, derivatives, salts or combinations thereof.
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10. The composition of claim 7, wherein the nitric oxide donor comprises a component selected from the group consisting of S-nitrosothiols, nitrites, N-oxo-N-nitrosamines, substrates of nitric oxide synthase, diazenium diolates and any analogs, homologues, congeners, derivatives, salts and combinations thereof.
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11. The composition of claim 1, wherein L1 or L2 comprises a component selected from a group consisting of amides, esters, anhydrides, orthoesters, all-aromatic carbonates, ureas, urethanes, semicarbazones, imines, oximes, ketals, acetals, disulfides, or a combination thereof.
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12. A composition comprising a blend, wherein the blend comprises the composition of claim 1 and an agent.
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13. The composition of claim 12, wherein R1 or R3 comprises an aromatic radical.
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14. The composition of claim 13, wherein the aromatic radical comprises a component selected from the group consisting of p-phenylene, m-phenylene, o-phenylene, and derivatives thereof.
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15. The composition of claim 12, wherein
R1 comprises a phenylene radical or a derivative thereof; -
R2 and R4 each comprises a component independently selected from a group consisting of 1,3-propanediol, 1,4-butanediol, 1,6-hexanediol, and derivatives thereof; and R3 comprises a component selected from a group consisting of adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, and derivatives thereof.
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16. The composition of claim 12, wherein the agent comprises a component selected from a group consisting of poly(ethylene glycol), poly(propylene glycol), poly(N-vinyl pyrrolidone), phosphorylcholine, glycosaminoglycans, carboxymethylcellulose, hyaluronic acid, heparin, hirudin, poly(acrylamide methyl propane sulfonic acid), poly(styrene sulfonate), sulfonated dextran, dermatan sulfate, RGD, collagen, chitin, chitosan, elastin and any derivatives, analogs, homologues, congeners, salts, copolymers and combinations thereof.
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17. The composition of claim 12, wherein the agent comprises poly(ethylene glycol), poly(N-vinyl pyrrolidone), phosphorylcholine, hyaluronic acid, heparin, hirudin, or any derivatives, analogs, homologues, congeners, salts, copolymers or combinations thereof.
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18. The composition of claim 12, wherein the agent comprises a component selected from a group consisting of a free radical scavenger, a nitric oxide donor, rapamycin, everolimus, tacrolimus, paclitaxel, docetaxel, estradiol, clobetasol, idoxifen, tazarotene and any prodrugs, metabolites, analogs, homologues, congeners, and any derivatives, salts and combinations thereof.
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19. The composition of claim 18, wherein the free radical scavenger comprises a component selected from a group consisting of 2,2′
- ,6,6′
-tetramethyl-1-piperinyloxy, free radical;
4-amino-2,2′
,6,6′
-tetramethyl-1-piperinyloxy, free radical;
4-hydroxy-2,2′
,6,6′
-tetramethyl-piperidene-1-oxy, free radical;
2,2′
,3,4,5,5′
-hexamethyl-3-imidazolinium-1-yloxy methyl sulfate, free radical;
16-doxyl-stearic acid, free radical;
superoxide dismutase mimic; and
, any analogs, homologues, congeners, derivatives, salts and combinations thereof.
- ,6,6′
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20. The composition of claim 19, wherein the free radical scavenger comprises TEMPO or any analogs, homologues, congeners, derivatives, salts or combinations thereof.
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21. The composition of claim 19, wherein the nitric oxide donor comprises a component selected from the group consisting of S-nitrosothiols, nitrites, N-oxo-N-nitrosamines, substrates of nitric oxide synthase, diazenium diolates and any analogs, homologues, congeners, derivatives, salts and combinations thereof.
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22. A coating for a medical article comprising the composition of claim 1.
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23. The coating of claim 22, wherein the medical article comprises a stent.
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24. A medical article comprising the composition of claim 1.
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25. The medical article of claim 24, wherein the medical article comprises a stent.
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26. A coating for a medical article comprising the composition of claim 12.
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27. The coating of claim 26, wherein the medical article comprises a stent.
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28. A medical article comprising the composition of claim 12.
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29. The medical article of claim 28, wherein the medical article comprises a stent.
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58. A method comprising fabricating a medical article comprising an implantable substrate, wherein said fabricating comprises:
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(i) preparing a blend comprising the composition of claim 1 and an agent; and (ii) forming the medical article comprising an implantable substrate; (iii) optionally applying a coating comprising the blend on at least a portion of the implantable substrate; and (iii) optionally annealing the medical article or coating.
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59. The method of claim 58, wherein said medical article comprises a stent.
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60. The method of claim 58, wherein R1 or R3 comprises an aromatic radical.
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61. The method of claim 60, wherein the aromatic radical comprises a component selected from the group consisting of p-phenylene, m-phenylene, o-phenylene, and derivatives thereof.
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62. The method of claim 58, wherein
R1 comprises a phenylene radical or a derivative thereof; -
R2 and R4 each comprise a component independently selected from a group consisting of 1,3-propanediol, 1,4-butanediol, 1,6-hexanediol, and derivatives thereof; and R3 comprises a component selected from a group consisting of adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, and derivatives thereof.
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63. The method of claim 58, wherein the agent comprises a component selected from a group consisting of poly(ethylene glycol), poly(propylene glycol), poly(N-vinyl pyrrolidone), phosphorylcholine, glycosaminoglycans, carboxymethylcellulose, hyaluronic acid, heparin, hirudin, poly(acrylamide methyl propane sulfonic acid), poly(styrene sulfonate), sulfonated dextran, dermatan sulfate, RGD, collagen, chitin, chitosan, elastin and any derivatives, analogs, homologues, congeners, salts, copolymers and combinations thereof.
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64. The method of claim 58, wherein the agent comprises poly(ethylene glycol), poly(N-vinyl pyrrolidone), phosphorylcholine, hyaluronic acid, heparin, hirudin, or any derivatives, analogs, homologues, congeners, salts, copolymers or combinations thereof.
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65. The method of claim 58, wherein the agent comprises a component selected from a group consisting of a free radical scavenger, a nitric oxide donor, rapamycin, everolimus, tacrolimus, paclitaxel, docetaxel, estradiol, clobetasol, idoxifen, tazarotene and any prodrugs, metabolites, analogs, homologues, congeners, and any derivatives, salts and combinations thereof.
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66. The method of claim 65, wherein the free radical scavenger comprises a component selected from a group consisting of 2,2′
- ,6,6′
-tetramethyl-1-piperinyloxy, free radical;
4-amino-2,2′
,6,6′
-tetramethyl-1-piperinyloxy, free radical;
4-hydroxy-2,2′
,6,6′
-tetramethyl-piperidene-1-oxy, free radical;
2,2′
,3,4,5,5′
-hexamethyl-3-imidazolinium-1-yloxy methyl sulfate, free radical;
16-doxyl-stearic acid, free radical;
superoxide dismutase mimic; and
, any analogs, homologues, congeners, derivatives, salts and combinations thereof.
- ,6,6′
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67. The method of claim 65, wherein the free radical scavenger comprises TEMPO or any analogs, homologues, congeners, derivatives, salts or combinations thereof.
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68. The method of claim 65, wherein the nitric oxide donor comprises a component selected from the group consisting of S-nitrosothiols, nitrites, N-oxo-N-nitrosamines, substrates of nitric oxide synthase, diazenium diolates and any analogs, homologues, congeners, derivatives, salts and combinations thereof.
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69. The method of claim 58, wherein L1 or L2 comprises a component selected from a group consisting of amides, esters, anhydrides, orthoesters, all-aromatic carbonates, ureas, urethanes, semicarbazones, imines, oximes, ketals, acetals, disulfides, or a combination thereof.
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2. The composition of claim 1, wherein R1 or R3 comprise an aromatic radical.
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30. A medical article comprising a polymer represented by a formula:
- View Dependent Claims (31, 32, 33)
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31. The medical article of claim 30, wherein the polymer comprises block copolymer comprising a phenylene radical and an aliphatic radical.
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32. The medical article of claim 30 further comprising a coated implantable substrate.
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33. The medical article of claim 32, wherein the coated implantable substrate comprises a stent.
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31. The medical article of claim 30, wherein the polymer comprises block copolymer comprising a phenylene radical and an aliphatic radical.
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34. A stent comprising a coating, wherein the coating comprises a polymer represented by a formula:
- View Dependent Claims (35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45)
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35. The stent of claim 34, wherein the coating further comprises an agent that may be blended with, or connected to the coating.
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36. The stent of claim 34, wherein R1 or R3 comprise an aromatic radical.
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37. The stent of claim 36, wherein the aromatic radical comprises a component selected from the group consisting of p-phenylene, m-phenylene, o-phenylene and derivatives thereof.
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38. The stent of claim 34, wherein
R1 comprises a phenylene radical or a derivative thereof; -
R2 and R4 each comprise a component independently selected from a group consisting of 1,3-propanediol, 1,4-butanediol, 1,6-hexanediol, and derivatives thereof; and R3 comprises a component selected from a group consisting of adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, and derivatives thereof.
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39. The stent of claim 34, wherein the agent comprises a component selected from a group consisting of poly(ethylene glycol), poly(propylene glycol), poly(N-vinyl pyrrolidone), phosphorylcholine, glycosaminoglycans, carboxymethylcellulose, hyaluronic acid, heparin, hirudin, poly(acrylamide methyl propane sulfonic acid), poly(styrene sulfonate), sulfonated dextran, dermatan sulfate, RGD, collagen, chitin, chitosan, elastin and any derivatives, analogs, homologues, congeners, salts, copolymers and combinations thereof.
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40. The stent of claim 34, wherein the agent comprises poly(ethylene glycol), poly(N-vinyl pyrrolidone), phosphorylcholine, hyaluronic acid, heparin, hirudin, or any derivatives, analogs, homologues, congeners, salts, copolymers or combinations thereof.
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41. The stent of claim 34, wherein the agent comprises a component selected from a group consisting of a free radical scavenger, a nitric oxide donor, rapamycin, everolimus, tacrolimus, paclitaxel, docetaxel, estradiol, clobetasol, idoxifen, tazarotene and any prodrugs, metabolites, analogs, homologues, congeners, and any derivatives, salts and combinations thereof.
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42. The stent of claim 41, wherein the free radical scavenger comprises a component selected from a group consisting of 2,2′
- ,6,6′
-tetramethyl-1-piperinyloxy, free radical;
4-amino-2,2′
,6,6′
-tetramethyl-1-piperinyloxy, free radical;
4-hydroxy-2,2′
,6,6′
-tetramethyl-piperidene-1-oxy, free radical;
2,2′
,3,4,5,5′
-hexamethyl-3-imidazolinium-1-yloxy methyl sulfate, free radical;
16-doxyl-stearic acid, free radical;
superoxide dismutase mimic; and
, any analogs, homologues, congeners, derivatives, salts and combinations thereof.
- ,6,6′
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43. The stent of claim 41, wherein the free radical scavenger comprises TEMPO or any analogs, homologues, congeners, derivatives, salts or combinations thereof.
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44. The stent of claim 41, wherein the nitric oxide donor comprises a component selected from the group consisting of S-nitrosothiols, nitrites, N-oxo-N-nitrosamines, substrates of nitric oxide synthase, diazenium diolates and any analogs, homologues, congeners, derivatives, salts and combinations thereof.
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45. The stent of claim 34, wherein L1 or L2 comprises a component selected from a group consisting of amides, esters, anhydrides, orthoesters, all-aromatic carbonates, ureas, urethanes, semicarbazones, imines, oximes, ketals, acetals, disulfides, or a combination thereof.
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35. The stent of claim 34, wherein the coating further comprises an agent that may be blended with, or connected to the coating.
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46. A method comprising fabricating a medical article or coating, wherein the medical article or coating comprises an implantable substrate, and the method further comprises:
(a) preparing a polymer represented by a formula; - View Dependent Claims (47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57)
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47. The method of claim 46, wherein said medical article comprises a stent.
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48. The method of claim 46, wherein R1 or R3 comprises an aromatic radical.
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49. The method of claim 48, wherein the aromatic radical comprises a component selected from the group consisting of p-phenylene, m-phenylene, o-phenylene, and derivatives thereof.
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50. The method of claim 46, wherein
R1 comprises a phenylene radical or a derivative thereof; -
R2 and R4 each comprise a component independently selected from a group consisting of 1,3-propanediol, 1,4-butanediol, 1,6-hexanediol, and derivatives thereof; and R3 comprises a component selected from a group consisting of adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, and derivatives thereof.
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51. The method of claim 46, wherein the agent comprises a component selected from a group consisting of poly(ethylene glycol), poly(propylene glycol), poly(N-vinyl pyrrolidone), phosphorylcholine, glycosaminoglycans, carboxymethylcellulose, hyaluronic acid, heparin, hirudin, poly(acrylamide methyl propane sulfonic acid), poly(styrene sulfonate), sulfonated dextran, dermatan sulfate, RGD, collagen, chitin, chitosan, elastin and any derivatives, analogs, homologues, congeners, salts, copolymers and combinations thereof.
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52. The method of claim 46, wherein the agent comprises poly(ethylene glycol), poly(N-vinyl pyrrolidone), phosphorylcholine, hyaluronic acid, heparin, hirudin, or any derivatives, analogs, homologues, congeners, salts, copolymers or combinations thereof.
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53. The method of claim 46, wherein the agent comprises a component selected from a group consisting of a free radical scavenger, a nitric oxide donor, rapamycin, everolimus, tacrolimus, paclitaxel, docetaxel, estradiol, clobetasol, idoxifen, tazarotene and any prodrugs, metabolites, analogs, homologues, congeners, and any derivatives, salts and combinations thereof.
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54. The method of claim 53, wherein the free radical scavenger comprises a component selected from a group consisting of 2,2′
- ,6,6′
-tetramethyl-1-piperinyloxy, free radical;
4-amino-2,2′
,6,6′
-tetramethyl-1-piperinyloxy, free radical;
4-hydroxy-2,2′
,6,6′
-tetramethyl-piperidene-1-oxy, free radical;
2,2′
,3,4,5,5′
-hexamethyl-3-imidazolinium-1-yloxy methyl sulfate, free radical;
16-doxyl-stearic acid, free radical;
superoxide dismutase mimic; and
, any analogs, homologues, congeners, derivatives, salts and combinations thereof.
- ,6,6′
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55. The method of claim 53, wherein the free radical scavenger comprises TEMPO or any analogs, homologues, congeners, derivatives, salts or combinations thereof.
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56. The method of claim 53, wherein the nitric oxide donor comprises a component selected from the group consisting of S-nitrosothiols, nitrites, N-oxo-N-nitrosamines, substrates of nitric oxide synthase, diazenium diolates and any analogs, homologues, congeners, derivatives, salts and combinations thereof.
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57. The method of claim 46, wherein said L1 or said L2 comprises a component selected from a group consisting of amides, esters, anhydrides, orthoesters, all-aromatic carbonates, ureas, urethanes, semicarbazones, imines, oximes, ketals, acetals, disulfides, or a combination thereof.
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47. The method of claim 46, wherein said medical article comprises a stent.
Specification
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Current AssigneeAdvanced Cardiovascular Systems Incorporated
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Original AssigneeAdvanced Cardiovascular Systems Incorporated
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InventorsTang, Yiwen, Pacetti, Stephen D.
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Primary Examiner(s)BOYKIN, TERRESSA M
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Application NumberUS10/996,765Publication NumberTime in Patent Office895 DaysField of Search424/422, 424/423, 424/426, 514/2, 514/6, 514/28, 514/35, 528/480, 623/23, 623/57US Class Current528/190CPC Class CodesA61L 2300/114 Nitric oxide, i.e. NOA61L 2300/416 Anti-neoplastic or anti-pro...A61L 31/10 Macromolecular materialsA61L 31/148 Materials at least partiall...A61L 31/16 Biologically active materia...C08G 2230/00 Compositions for preparing ...C08G 63/181 Acids containing aromatic r...C08L 67/02 Polyesters derived from dic...