CA2664682A1 - N-substituted monomers and polymers - Google Patents

N-substituted monomers and polymers Download PDF

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Publication number
CA2664682A1
CA2664682A1 CA002664682A CA2664682A CA2664682A1 CA 2664682 A1 CA2664682 A1 CA 2664682A1 CA 002664682 A CA002664682 A CA 002664682A CA 2664682 A CA2664682 A CA 2664682A CA 2664682 A1 CA2664682 A1 CA 2664682A1
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formula
group
polymer
medical device
stent
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CA002664682A
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CA2664682C (en
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Earnest G. Baluca
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Reva Medical Inc
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Reva Medical, Inc.
Earnest G. Baluca
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
    • A61L31/04—Macromolecular materials
    • A61L31/06—Macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
    • A61L31/08—Materials for coatings
    • A61L31/10—Macromolecular materials
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
    • A61L31/14—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
    • A61L31/16—Biologically active materials, e.g. therapeutic substances
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
    • C08G63/685—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen
    • C08G63/6854—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/6856—Dicarboxylic acids and dihydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/04—Aromatic polycarbonates
    • C08G64/045—Aromatic polycarbonates containing aliphatic unsaturation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/04—Aromatic polycarbonates
    • C08G64/06—Aromatic polycarbonates not containing aliphatic unsaturation
    • C08G64/08—Aromatic polycarbonates not containing aliphatic unsaturation containing atoms other than carbon, hydrogen or oxygen
    • C08G64/12—Aromatic polycarbonates not containing aliphatic unsaturation containing atoms other than carbon, hydrogen or oxygen containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/18—Block or graft polymers
    • C08G64/183—Block or graft polymers containing polyether sequences
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/18—Block or graft polymers
    • C08G64/186—Block or graft polymers containing polysiloxane sequences
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G79/00—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule
    • C08G79/02—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule a linkage containing phosphorus
    • C08G79/04—Phosphorus linked to oxygen or to oxygen and carbon
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L85/00—Compositions of macromolecular compounds obtained by reactions forming a linkage in the main chain of the macromolecule containing atoms other than silicon, sulfur, nitrogen, oxygen and carbon; Compositions of derivatives of such polymers
    • C08L85/02—Compositions of macromolecular compounds obtained by reactions forming a linkage in the main chain of the macromolecule containing atoms other than silicon, sulfur, nitrogen, oxygen and carbon; Compositions of derivatives of such polymers containing phosphorus
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B33—ADDITIVE MANUFACTURING TECHNOLOGY
    • B33Y—ADDITIVE MANUFACTURING, i.e. MANUFACTURING OF THREE-DIMENSIONAL [3-D] OBJECTS BY ADDITIVE DEPOSITION, ADDITIVE AGGLOMERATION OR ADDITIVE LAYERING, e.g. BY 3-D PRINTING, STEREOLITHOGRAPHY OR SELECTIVE LASER SINTERING
    • B33Y80/00—Products made by additive manufacturing

Abstract

Described herein are N-substituted monomers and polymers, methods of making such monomers and polymers, and methods of using them in various applications, such as medical devices. In preferred embodiments, the medical device is a stent.

Claims (70)

WHAT IS CLAIMED IS:
1. A polymer that comprises a recurring unit of the formula (1):
wherein:
X1 and X2 in formula (I) are each independently selected from the group consisting of Br and I;
y1 and y2 in formula (I) are each independently zero or an integer in the range of 1 to 4;
A1 in formula (I) is selected from the group consisting of R3 in formula (I) is selected from the group consisting of C1 - C30 alkyl, C1 -C30 heteroalkyl, C5 - C30 aryl, C6 - C30 alkylaryl, and C2 - C30 heteroaryl;

R4 in formula (I) selected from the group consisting of H, C1 - C30 alkyl, and C1 - C30 heteroalkyl;
R1 in formula (I) is Z in formula (I) is O or S;
R5 and R6 in formula (I) are each independently selected from the group consisting of -CH=CH-, -CHJ1-CHJ2-, and -(CH2)a-;

a in formula (I) is zero or an integer in the range of 1 to 8;
J1 and J2 in formula (I) are each independently selected from the group consisting of H, Br, and I;
Q in formula (I) is a group comprising about 20 or more carbon atoms;
R x in formula (I) is selected from optionally substituted branched or unbranched C1 - C30 alkyl and optionally substituted C6 - C30 aryl; and R y in formula (I) is selected from hydrogen, optionally substituted branched, or unbranched C1 - C30 alkyl and optionally substituted C6 - C30 aryl.
2. The polymer according to Claim 1, wherein R x in formula (I) is a branched or unbranched C1 - C6 alkyl.
3. The polymer according to Claim 1, wherein R x in formula (I) is a methyl.
4. The polymer according to any one of Claims 1 to 3, wherein:

X1 and X2 in formula (I) are each 1;
A1 in formula (I) is R1 in formula (I) is Z in formula (I) is O; and R5 and R6 in formula (I) are each independently selected from the group consisting of-CH=CH- and -(CH2)a-.
5. The polymer according to Claim any one of Claims 1 to 4, wherein Q in formula (I) comprises from about 20 to about 30 carbon atoms.
6. The polymer according any one of Claims 1 to 4, wherein Q in formula (I) is a group that comprises the formula (VII):

wherein n1 in formula (VII) is an integer in the range of about 1 to about 1,000.
7. The polymer to any one of Claims 1 to 3, wherein R5 in formula (I) is -CH-CH- or -(CH2)a-; R6 in formula (I) is -(CH2)a-; and Q in formula (I) is an ester group comprising from about 20 to about 30 carbon atoms.
8. The polymer to any one of Claims 1 to 7, wherein Z in formula (1) is O or S

and J1 and J2 in formula (I) are each independently selected from the group consisting of Br and I.
9. The polymer according to any one of Claims 1 to 8, further comprising a recurring unit of the formula (II):

wherein R7 in formula (II) is H or CH3; A3 in formula (II) is a chemical group having a molecular weight of about 500 or less; and A3 in formula (II) bears at least one heavy atom attached to the polymer.
10. The polymer of according to any one of Claims 1 to 9, further comprising a recurring unit of the formula (III):

wherein R8 in formula (III) is H or CH3; L3 in formula (III) is an ester or amide linkage; and R9 in formula (III) comprises a C6 - C30 hydrocarbon group.
11. The polymer according to any one of Claims 1 to 10, further comprising a recurring unit of the formula (IV):

wherein A4 in formula (IV) represents H or a chemical group containing from about 1 to about 30 carbons; A3 in formula (IV) is a chemical group having a molecular weight of about 500 or less; and A3 in formula (IV) bears at least one heavy atom attached to the polymer.
12. The polymer according to any one of Claims 1 to 11, further comprising a recurring unit of the formula (V):

wherein R10 in formula (V) comprises a C6 to C30 hydrocarbon group and R11 in formula (V) represents H or a C1 to C30 hydrocarbon group.
13. The polymer according to any one of Claims 1 to 12, further comprising a recurring unit of the formula (VI):

wherein R12 in formula (VI) is H or CH3 and n4 in formula (VI) is an integer in the range of about 1 to about 1,000.
14. A method for making a polymer according to any one of Claims 1 to 13 comprising attaching an N-substituent during the synthesis of a corresponding monomer.
15. A method for making a polymer according to any one of Claims 1 to 13 comprising attaching an N-substituent after polymerization of a corresponding monomer.
16. A medical device comprising a polymer according to any one of Claims 1 to 13.
17. The medical device of Claim 16, wherein the medical device comprises a stent.
18. The medical device of Claim 17, wherein the stent is selected from the group consisting of a sheet stent, a braided stent, a self-expanding stent, a wire stent, a deformable stent, and a slide-and-lock stent.
19. The medical device of Claim 18, wherein the self-expanding stent comprises a heat expandable portion that is temperature-dependent-expandable.
20. The medical device of Claim 19, wherein the heat expandable portion is expandable at a temperature above a melting point of the polymer.
21. The medical device of any one of Claims 17 to 20 wherein at least a portion of the polymer is positioned at a surface of the stent.
22. The medical device of Claim 16, wherein the polymer forms a coating on at least a portion of the medical device.
23. The medical device of according to any one of Claims 16 to 22 that further comprises an effective amount of at least one therapeutic agent.
24. The medical device of Claim 23, wherein the therapeutic agent is selected from the group consisting of antiproliferative agent, anti-inflammatory agent, anti-matrix metalloproteinase agent, lipid lowering agent, cholesterol modifying agent, anti-thrombotic agent, and antiplatelet agent.
25. The medical device of Claim 23, wherein the effective amount is sufficient to provide an effect selected from the group consisting of inhibition of restenosis, inhibition of thrombosis, inhibition of plaque formation, inhibition of plaque rupture, inhibition of inflammation, lowering of cholesterol, and promote healing.
26. An inherently radiopaque, biocompatible, bioresorbable polymer comprising one or more recurring units of the formula (la):

wherein:
X1 and X2 in formula (Ia) are each independently selected from the group consisting of Br and I;

y1 and y2 in formula (Ia) are each independently zero or an integer in the range of 1 to 4, with the proviso that the sum of y1 and y2 in formula (Ia) is at least 1;
R1 in formula (Ia) is R x in formula (Ia) is selected from optionally substituted branched or unbranched C1-C30 alkyl and optionally substituted C6 - C30 aryl;
R13 and R14 in formula (Ia) are each independently selected from the group consisting of -CH=CH-, -(CH2)c-, -(CHJ1)-, -CHJ2-CHJ3-, -CH=CH-(CHJ1)-, and -(CH2)c,-(CHJ1)-;
c in formula (Ia) is zero or an integer in the range of 1 to 8;

J1, J2 and J3 in formula (Ia) are each independently selected from the group consisting of H, Br, I, -NH-Q2 and -C(=Z8)-OQ3;
Q1, Q2 and Q3 in formula (Ia) are each independently H, a group comprising from about I to about 30 carbons, or a group that comprises the formula (VIIa):

wherein n1 in formula (VIIa) is an integer in the range of about 1 to about 1,000;
Z7 and Z8 in formula (Ia) are each independently O or S;
A1 in formula (Ia) is selected from the group consisting of R5 in formula (Ia) is selected from the group consisting of H, C1 - C30 alkyl, and C1 - C30 heteroalkyl.
27. The polymer according to Claim 26, wherein R x in formula (Ia) is a branched or unbranched C1 - C6 alkyl.
28. The polymer according to Claim 26, wherein R x in formula (Ia) is methyl.
29. The polymer according to any one of Claims 26 to 28, wherein Q1, Q2 and Q3 in formula (Ia) are each independently H or a non-crystallizable group comprising from about 1 to about 30 carbons.
30. The polymer according to any one of Claims 26 to 29, wherein at least one of Q1, Q2 and Q3 in formula (Ia) is a group comprising from about 20 to about 30 carbons.
31. The polymer according to to any one of Claims 26 to 30, wherein at least one of Ql, Q2 and Q3 in formula (Ia) is a group comprising the formula (VIIa):

wherein n 1 in formula (VIIa) is an integer in the range of about 1 to about 1,000.
32. The polymer according to any one of Claims 26 to 31, wherein:
X1 and X2 in formula (Ia) are each I;
R1 in formula (Ia) is Z7 in formula (Ia) is O; and R13 and R14 in formula (Ia) are each independently selected from the group consisting of -CH=CH- and -(CH2)c-.
33. The polymer according to to any one of Claims 26 to 32, further comprising one or more recurring units of the formula (IIa):

wherein :
B in formula (IIa) is -O-((CHR6)p-O)q-;
R6 in formula (IIa) is H or C1 to C3 alkyl;

p and q in formula (IIa) are each individually an integer in the range of about 1 to about 100;
A2 in formula (IIa) is selected from the group consisting of R7 in formula (IIa) is H or a C1 - C30 hydrocarbon; and R11 in formula (IIa) is selected from the group consisting of C1 - C30 alkyl, -C30 heteroalkyl, C5 - C30 aryl, C6 - C30 alkylaryl, and C2 - C30 heteroaryl.
34. The polymer of to any one of Claims 26 to 33, further comprising one or more recurring units of the formula (Ib):

wherein:

X3 and X4 in formula (Ib) are each independently selected from the group consisting of Br and 1;

y3 and y4 in formula (Ib) are each independently zero or an integer in the range of 1 to 4;

R2 in formula (Ib) is selected from the group consisting of:
and R x in formula (Ib) is selected from optionally substituted branched or unbranched C1- C30 alkyl and optionally substituted C6 - C30 aryl;

R8 and R9 in formula (Ib) are each independently H or a non-crystallizable C1 to C30 hydrocarbon;
Z4, Z5 and Z6 in formula (Ib) are each independently O or S;
a and b in formula (Ib) are each independently an integer in the range of 1 to 8;
A3 in formula (Ib) is selected from the group consisting of R10 in formula (Ib) is selected from the group consisting of H, C1 - C30 alkyl, and C1 - C30 heteroalkyl; and R12 in formula (Ib) is selected from the group consisting of C1 - C30 alkyl, - C30 heteroalkyl, C5 - C30 aryl, C6 - C30 alkylaryl, and C2 - C30 heteroaryl.
35. The polymer of to any one of Claims 26 to 31 or Claims 33 to 34, wherein in formula (Ia) is wherein R x in formula (Ia) is selected from optionally substituted branched or unbranched C1 - C30 alkyl and optionally substituted C6 - C30 aryl;

R3 in formula (Ia) is H or a non-crystallizable C1 to C29 hydrocarbon;

Z1 and Z2 in formula (Ia) are each independently O or S; and m in formula (Ia) is an integer in the range of 1 to 8.
36. The polymer of any one of Claims 26 to 31 or Claims 33 to 34, wherein R1 in formula (Ia) is wherein R x in formula (Ia) is selected from optionally substituted branched or unbranched C1 - C30 alkyl and optionally substituted C6 - C30 aryl;

R3 in formula (Ia) is H or a non-crystallizable C1 to C29 hydrocarbon;
Z1 and Z2 in formula (Ia) are each independently O or S; and j and m in formula (Ia) are each independently an integer in the range of 1 to 8.
37. The polymer of any one of Claims 26 to 31 or Claims 33 to 34, wherein R1 in formula (Ia) is wherein R x in formula (Ia) is selected from optionally substituted branched or unbranched C1 - C30 alkyl and optionally substituted C6 - C30 aryl;

R3 and R4 in formula (la) are each independently H or a non-crystallizable C1 to C29 hydrocarbon;
Z1, Z2 and Z3 in formula (Ia) are each independently O or S; and j and m in formula (Ia) are each independently an integer in the range of 1 to 8.
38. A method for making a polymer of any one of Claims 26 to 37 comprising attaching an N-substituent during the synthesis of a corresponding monomer.
39. A method for making a polymer of any one of Claims 26 to 37 comprising attaching an N-substituent during polymerization of a corresponding monomer.
40. A method for making a polymer of any one of Claims 26 to 37 comprising attaching an N-substituent after polymerization of a corresponding monomer.
41. A medical device comprising a polymer of any one of Claims 26 to 37.
42. The medical device of Claim 41, wherein the medical device comprises a stent.
43. The medical device of Claim 42, wherein the stent is selected from the group consisting of a sheet stent, a braided stent, a self-expanding stent, a wire stent, a deformable stent, and a slide-and-lock stent.
44. The medical device of Claim 43, wherein the self-expanding stent comprises a heat expandable portion that is temperature-dependent-expandable.
45. The medical device of Claim 44, wherein the heat expandable portion is expandable at a temperature above a melting point of the polymer.
46. The medical device of any one of Claims 42 to 45 wherein at least a portion of the polymer is positioned at a surface of the stent.
47. The medical device of Claim 41, wherein the polymer forms a coating on at least a portion of the medical device.
48. The medical device of any of Claims 41 to 47 that further comprises an effective amount of at least one therapeutic agent.
49. The medical device of Claim 48, wherein the therapeutic agent is selected from the group consisting of antiproliferative agent, anti-inflammatory agent, anti-matrix metalloproteinase agent, lipid lowering agent, cholesterol modifying agent, anti-thrombotic agent, and antiplatelet agent.
50. The medical device of Claim 48, wherein the effective amount is sufficient to provide an effect selected from the group consisting of inhibition of restenosis, inhibition of thrombosis, inhibition of plaque formation, inhibition of plaque rupture, inhibition of inflammation, lowering of cholesterol, and promote healing.
51. A polymer that comprises a recurring unit of the formula (XI):
wherein X1 and X2 in formula (XI) are each independently selected from the group consisting of Br and I;

y1 and y2 in formula (XI) are each independently zero or an integer in the range of 1 to 4(XI);

M1, M2, and M3 in formula (XI) are each independently selected from O or S;
Q2 in formula (XI) is selected from O or NR y;

R x in formula (XI) is optionally substituted branched or unbranched C1 - C30 alkyl or optionally substituted C6 - C30 aryl;

R y in formula (XI) is selected from hydrogen, optionally substituted branched, or unbranched C1 - C30 alkyl and optionally substituted C6 - C30 aryl; and BA2 in formula (XI) is an optionally substituted branched or unbranched C1-C20 alkyl or aryl, or comprises a bioactive moiety selected from the group consisting of polyethylene glycol (PEG), poly(propylene glycol) (PPG), poly(tetramethylene glycol), dihydroxy polyvinylpyrrolidone (PVP), dihydroxy poly(styrene sulfonate) (HPSS), poly(2-hydroxyethyl methacrylates) (PHEMA), poly(3-hydroxypropyl methacrylates), poly(3-hydroxypropyl methacrylamide) (PHPMA), poly(alkoxy methacrylates), poly(alkoxy acrylates), polyarginine peptides (PAP), phosphoryl choline (PC), dextran, dextrin, sulfonated dextran, dermatan sulfate, heparin (HEP), chondroitan sulfate, glycosaminoglycans, chitosan, sodium hyaluronate, and hyaluronic acid (HA).
52. The polymer according to Claim 51, wherein R x in formula (XI) is a branched or unbranched C1 - C6 alkyl.
53_ The polymer according to Claim 51, wherein R x in formula (XI) is methyl.
54. The polymer according to any of Claims 51 to 53, wherein M1, M2, and M3 in formula (XI) are each independently selected from O or NH.
55. The polymer according to any of Claims 51 to 54, further comprising one or more recurring units of the formula (XII):

wherein M4 in formula (XII) is O, NH, or S;

Q1 and Q3 in formula (XII) are each independently selected from O or NR Y;
R y in formula (XII) is selected from hydrogen, optionally substituted branched, or unbranched C1- C30 alkyl and optionally substituted C6 - C30 aryl; and BA1 in formula (XII) is an optionally substituted branched or unbranched C1-C20 alkyl or aryl, or comprises a bioactive moiety selected from the group consisting of polyethylene glycol (PEG), poly(propylene glycol) (PPG), poly(tetramethylene glycol), dihydroxy polyvinylpyrrolidone (PVP), dihydroxy poly(styrene sulfonate) (HPSS), poly(2-hydroxyethyl methacrylates) (PHEMA), poly(3-hydroxypropyl methacrylates), poly(3-hydroxypropyl methacrylamide) (PHPMA), poly(alkoxy methacrylates), poly(alkoxy acrylates), polyarginine peptides (PAP), phosphoryl choline (PC), dextran, dextrin, sulfonated dextran, dermatan sulfate, heparin (HEP), chondroitan sulfate, glycosaminoglycans, chitosan, sodium hyaluronate, and hyaluronic acid (HA).
56. The polymer according to any of Claims 51 to 55, further comprising one or more recurring units of the formula (XIII):

wherein r in formula (XIII) is an integer in the range of from about 1 to about 12.
57. The polymer according to any of Claims 51 to 56, further comprising one or more recurring units of the formula (XIV):

wherein s in formula (XIV) is an integer in the range of from about 2 to about
58. A method for making a polymer of any of Claims 51 to 57 comprising attaching an N-substituent during the synthesis of a corresponding monomer.
59. A method for making a polymer of any of Claims 51 to 57 comprising attaching an N-substituent during polymerization of a corresponding monomer.
60. A method for making a polymer of any of Claims 51 to 57 comprising attaching an N-substituent after polymerization of a corresponding monomer.
61. A medical device comprising a polymer of any of Claims 51 to 57.
62. The medical device of Claim 61, wherein the medical device comprises a stent.
63. The medical device of Claim 62, wherein the stent is selected from the group consisting of a sheet stent, a braided stent, a self-expanding stent, a wire stent, a deformable stent, and a slide-and-lock stent.
64. The medical device of Claim 63, wherein the self-expanding stent comprises a heat expandable portion that is temperature-dependent-expandable.
65. The medical device of Claim 64, wherein the heat expandable portion is expandable at a temperature above a melting point of the polymer.
66. The medical device of any of Claims 62 to 65, wherein at least a portion of the polymer is positioned at a surface of the stent.
67. The medical device of Claim 61, wherein the polymer forms a coating on at least a portion of the medical device.
68. The medical device of any of Claims Claim 61 to 67 that further comprises an effective amount of at least one therapeutic agent.
69. The medical device of Claim 68, wherein the therapeutic agent is selected from the group consisting of antiproliferative agent, anti-inflammatory agent, anti-matrix metalloproteinase agent, lipid lowering agent, cholesterol modifying agent, anti-thrombotic agent, and antiplatelet agent.
70. The medical device of Claim 68, wherein the effective amount is sufficient to provide an effect selected from the group consisting of inhibition of restenosis, inhibition of thrombosis, inhibition of plaque formation, inhibition of plaque rupture, inhibition of inflammation, lowering of cholesterol, and promote healing.
CA2664682A 2006-10-17 2007-10-16 N-substituted monomers and polymers Expired - Fee Related CA2664682C (en)

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