US2006217525A1PendingUtilityA1
Degradable polymers and methods of preparation thereof
Assignee: WRIGHT DAVIS BIOMEDICAL TECHNOPriority: Dec 22, 2004Filed: Dec 21, 2005Published: Sep 28, 2006
Est. expiryDec 22, 2024(expired)· nominal 20-yr term from priority
A61K 6/884A61L 31/10C08G 63/68A61L 17/145A61L 27/50A61L 27/34A61L 27/58A61L 17/10A61L 31/148C08L 101/16A61L 27/14C08G 63/688
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Claims
Abstract
The present invention provides polymers which substantially degrade in the presence of one or more triggers, preferably light energy or hydrogen peroxide, but does not substantially degrade in the absence of one or more triggers.
Claims
exact text as granted — not AI-modified1 . A biocompatible polymer, wherein the polymer substantially degrades in the presence of one or more triggers but does not substantially degrade under physiological conditions in the absence of one or more triggers.
2 . The polymer of claim 1 , wherein at least one trigger is light energy.
3 . The polymer of claim 1 , wherein at least one trigger is hydrogen peroxide.
4 . The polymer of claim 1 , wherein the polymer substantially degrades through the cleavage of carbon-oxygen bonds, carbon-nitrogen bonds, carbon-boron bonds, nitrogen-nitrogen bonds, sulfur-sulfur bonds, boron-oxygen bonds, oxygen-phosphorous bonds, or a combination thereof.
5 . The polymer of claim 4 , wherein the polymer substantially degrades through the cleavage of carbon-oxygen bonds, carbon-boron bonds, sulfur-sulfur bonds, boron-oxygen bonds, or a combination thereof.
6 . The polymer of claim 5 , wherein the polymer substantially degrades through the cleavage of carbon-oxygen bonds, or sulfur-sulfur bonds, and at least one trigger is light energy.
7 . The polymer of claim 5 , wherein the polymer substantially degrades through the cleavage of carbon-boron bonds and optionally boron-oxygen bonds, and at least one trigger is hydrogen peroxide.
8 . The polymer of claim 7 , wherein the polymer comprises carbon-boron bonds and optionally boron-oxygen bonds in the backbone of the polymer.
9 . The polymer of claim 8 , wherein the carbon-boron bonds are sp 2 carbon-boron bonds.
10 . The polymer of claim 9 , wherein the carbon-boron bonds are aryl-boron bonds.
11 . The polymer of claim 10 , wherein the boron atoms of the carbon-boron bonds in the backbone of the polymer have the substitution:
wherein,
Ar is an aryl or heteroaryl moiety that is part of the polymer backbone;
R is an alkyl moiety that is part of the polymer backbone;
R′ is H or lower alkyl; and
R″ is H or lower alkyl,
wherein optionally R and R′ together with any intervening atoms form a 5- to 7-membered ring.
12 . The polymer of claim 2 , wherein the polymer substantially degrades through one or more electrocyclic or retro-cycloaddition reactions.
13 . The polymer of claim 2 , wherein the polymer substantially degrades through homolytic cleavage of one or more chemical bonds.
14 . The polymer of claim 3 , wherein the polymer substantially degrades through oxidation of atoms in the polymer.
15 . The biocompatible polymer of claim 1 , wherein:
a) the polymer substantially degrades in the presence of both a first and second trigger; and b) the polymer does not substantially degrade in the presence of either the first or second trigger alone.
16 . The polymer of claim 15 , wherein the first or second trigger is light energy.
17 . The polymer of claim 16 , wherein the light energy is of a suitable wavelength to induce homolytic cleavage of one or more chemical bonds of the polymer.
18 . The polymer of claim 17 , wherein the light energy has a wavelength in the ultraviolet region.
19 . The polymer of claim 15 , wherein the first or second trigger is hydrogen peroxide.
20 . The polymer of claim 15 , wherein the polymer substantially degrades through homolytic cleavage of one or more chemical bonds.
21 . The polymer of claim 15 , wherein the polymer substantially degrades through the cleavage of carbon-oxygen bonds, carbon-nitrogen bonds, carbon-boron bonds, nitrogen-nitrogen bonds, sulfur-sulfur bonds, boron-oxygen bonds, oxygen-phosphorous bonds, or a combination thereof.
22 . The polymer of claim 21 , wherein the polymer substantially degrades through the cleavage of carbon-oxygen bonds, carbon-boron bonds, sulfur-sulfur bonds, boron-oxygen bonds, or a combination thereof.
23 . The polymer of claim 22 , wherein the polymer substantially degrades through the cleavage of sulfur-sulfur bonds and the first trigger is light energy and the second trigger is hydrogen peroxide.
24 . The polymer of claim 23 , wherein the polymer comprises sulfur-sulfur bonds in the backbone of the polymer.
25 . The polymer of claim 24 , wherein the polymer comprises substituted or unsubstituted bis(aminoaryl)-disulfide monomers.
26 . The polymer of claim 25 , wherein the polymer comprises substituted or unsubstituted bis(4-aminophenyl)-disulfide monomers.
27 . The polymer of claim 25 , wherein the polymer further comprises substituted or unsubstituted adipic acid, terephthalic acid, or PEG diacid monomers.
28 . The polymer of claim 23 , wherein the light energy has a wavelength in the ultraviolet region.
29 . The polymer of claim 28 , wherein the light energy has a wavelength of between about 250 and 270 nm.
30 . The polymer of claim 15 , wherein the polymer is represented according to Formula III:
wherein,
Ar, independently for each occurrence, is an aryl or heteroaryl group;
U is O or S;
Y is NR″, S, or O;
L is a linking group;
R″ is H or lower alkyl; and
m is an integer greater than 10.
31 . A method for the degradation of a polymer in a patient, comprising:
a) subjecting the polymer to an amount of a first trigger; and b) subjecting the polymer to an amount of a second trigger in the presence of the first trigger; thereby degrading the polymer in the patient, wherein the polymer substantially degrades in the presence of both the first and second trigger, and the polymer does not substantially degrade in the presence of either the first or second trigger alone.
32 . The method of claim 31 , wherein the first trigger is hydrogen peroxide and the second trigger is light energy.
33 . The method of claim 32 , wherein the polymer comprises sulfur-sulfur bonds in the backbone of the polymer and the light energy is of a suitable wavelength to induce homolytic cleavage of one or more of the sulfur-sulfur bonds.
34 . The method of claim 33 , wherein the light energy has a wavelength in the ultraviolet region.
35 . The method of claim 34 , wherein the light energy has a wavelength of between about 250 and 270 nm.
36 . The method of claim 31 , wherein the first trigger is light energy and the second trigger is hydrogen peroxide.
37 . The method of claim 31 , wherein the polymer substantially degrades through the cleavage of carbon-oxygen bonds, carbon-nitrogen bonds, carbon-boron bonds, nitrogen-nitrogen bonds, sulfur-sulfur bonds, boron-oxygen bonds, oxygen-phosphorous bonds, or a combination thereof.
38 . The method of claim 37 , wherein the polymer substantially degrades through the cleavage of sulfur-sulfur bonds.
39 . The method of claim 31 , wherein the polymer is represented according to Formula III:
wherein,
Ar, independently for each occurrence, is an aryl or heteroaryl group;
U is O or S;
Y is NR″, S, or O;
L is a linking group;
R″ is H or lower alkyl; and
m is an integer greater than 10.
40 . A biocompatible implant, comprising the polymer of claim 1 .
41 . The implant of claim 40 , wherein the implant is a suture.
42 . The implant of claim 40 , wherein the implant is a clip.
43 . The implant of claim 40 , wherein the implant is a partition for separating tissues in the body of a patient.
44 . The implant of claim 40 , wherein the implant is a stent.
45 . A coating, comprising the polymer of claim 1 .
46 . The coating of claim 45 , wherein the coating is an adhesive.
47 . The coating of claim 45 , wherein the adhesive is suitable for oral applications.
48 . The coating of claim 47 , wherein the oral applications comprise dental applications.
49 . The coating of claim 48 , wherein the dental applications comprise permanent or temporary fixation of a natural or synthetic tooth or tooth component.
50 . The coating of claim 47 , wherein the oral applications comprise orthodontic applications.
51 . The coating of claim 50 , wherein the orthodontic applications comprise temporary fixation of a device or structure to a tooth.
52 . The coating of claim 45 , wherein the coating is a barrier.
53 . A composition comprising a polymer of claim 1 and one or more therapeutic agents.
54 . A method for the preparation of a polymer according to Formula III:
comprising reacting a monomer of Formula A with a monomer of Formula B or a monomer of Formula C under reaction conditions:
thereby preparing the polymer of Formula III, wherein,
Ar, independently for each occurrence, is an aryl or heteroaryl group;
U is O or S;
X is a leaving group;
Y is NR″, S, or O;
L is a linking group;
R″ is H or lower alkyl; and
m is an integer greater than 10.
55 . The method of claim 54 , wherein one or more occurrences of Ar is a substituted or unsubstituted phenyl group.
56 . The method of claim 54 , wherein U is O.
57 . The method of claim 54 , wherein X is a halogen.
58 . The method of claim 54 , wherein Y is NH.
59 . The method of claim 54 , wherein L is alkylene.
60 . The method of claim 59 , wherein L is butylene.
61 . The method of claim 54 , wherein in the monomer of Formula B, L is substituted or unsubstituted phenyl.
62 . The method of claim 54 , where in the reaction conditions comprise a base.
63 . The method of claim 63 , wherein the base is an amine base.
64 . The method of claim 64 , wherein the base is pyridine.
65 . The method of claim 54 , wherein the reaction conditions comprise a polar organic solvent.
66 . The method of claim 54 , wherein the polar organic solvent is acetonitrile, DMSO, DMF, or N-methylpyrrolidinone (NMP).
67 . The method of claim 54 , wherein the polar organic solvent is N-methylpyrrolidinone (NMP).Join the waitlist — get patent alerts
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