Mono-layer thin film adhesive compounds and methods of synthesis and use

Patent metadata

Field	Value
Publication number	US-10238767-B2
Application number	US-201313951182-A
Country	US
Kind code	B2
Filing date	Jul 25, 2013
Priority date	Jul 25, 2012
Publication date	Mar 26, 2019
Grant date	Mar 26, 2019

Abstract

The invention relates provides synthetic medical adhesives which exploit plant derivatives to form covalent bonds with amines and thiols on tissue surfaces.

First claim

What is claimed is:

1. A coating comprising
a) a compound comprising the formula (I)

wherein
each L 2 , L 3 and L 4 independently, is a linker;
each L 1 , L 5 , L 6 , L 7 , L 8 , L 9 , L 10 , L 11 L 12 and L 13 independently, is a linker or a suitable linking group selected from amine, amide, ether, ester, urea carbonate or urethane linking groups;
each X 1 , X 2 , X 3 and X 4 independently, is an oxygen atom or NR;
R, if present, is H or a branched or unbranched C1-C10 alkyl group;
each R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 and R 14 independently, is a branched or unbranched C1-C15 alkyl group;
each PD ii and PD jj , independently, is a phenyl derivative residue selected from the group consisting of ferulic acid, isoferulic acid, sinapinic acid, syringic acid and vanillic acid;
aa is a value from 0 to about 80;
bb is a value from 0 to about 80;
cc is a value from 0 to about 80;
dd is a value from 1 to about 120;
ee is a value from 1 to about 120;
ff is a value from 1 to about 120;
gg is a value from 1 to about 120; and
hh is a value from 1 to about 80 and
b) an oxidant comprising tetraethylammonium periodate or tetrapropylammonium periodate.

2. The coating of claim 1 , wherein L 2 is a residue of a C1-C15 alkyl lactone or lactam, a poly C1-C15 alkyl lactone or lactam, a polyester, or a compound comprising the formula Y 4 —R 17 —C(═O)—Y 6 , wherein Y 4 is OH, NHR, a halide, or an activated derivative of OH or NHR;
R 17 is a branched or unbranched C1-C15 alkyl group; and
Y 6 is NHR, a halide, or OR.

3. The coating of claim 2 , wherein said alkyl lactone is a polycaprolactone.

4. The coating of claim 1 , wherein L 3 is a residue of an alkylene diol, an alkylene diamine or a poly(alkylene oxide) polyether or derivative thereof.

5. The coating of claim 4 , wherein L 3 is a poly(alkylene oxide) or —O—CH 2 CH 2 —O—CH 2 CH 2 —O—.

6. The coating of claim 1 , wherein L 2 or L 4 is a residue of a C1-C15 alkyl lactone or lactam, a poly C1-C15 alkyl lactone or lactam, or a compound comprising the formula Y 4 —R 17 —C(═O)—Y 6 , wherein Y 4 is OH, NHR, a halide, or an activated derivative of OH or NHR;
R 17 is a branched or unbranched C1-C15 alkyl group; and
Y 6 is NHR, a halide, or OR.

7. The coating of claim 6 , wherein said alkyl lactone is polycaprolactone.

8. The coating of claim 1 , wherein X 1 , X 2 , X 3 and X 4 are each O or NH.

9. The coating of claim 1 , wherein R 3 , R 6 , R 10 and R 13 are each —CH 2 CH 2 —.

10. The coating of claim 1 , wherein X 1 , X 2 , X 3 and X 4 are each O.

11. The coating of claim 1 , wherein R 4 , R 5 , R 9 and R 12 are each —CH 2 —.

12. The coating of claim 1 , wherein R 1 , R 2 , R 7 , R 9 , R 11 and R 14 are a branched or unbranched alkane.

13. The coating of claim 12 , wherein R 1 , R 2 , R 7 , R 9 , R 11 and R 14 are CH 2 —CH 2 — or —CH 2 —CH 2 —CH 2 —.

14. The coating of claim 1 , wherein L 1 , L 5 , L 6 , L 7 , L 8 , L 9 , L 19 , L 11 , L 12 , and L 13 form an amide, ester or carbamate.

15. The coating of claim 1 , wherein
L 2 is a residue of a polycaprolactone, a caprolactone, a polylactic acid, a polylactone or a lactic acid or lactone;
L 3 is a residue of polyethylene glycol;
L 4 is a residue of a polycaprolactone, a caprolactone, a polylactic acid, a polylactone or a lactic acid or lactone;
X 1 , X 2 , X 3 and X 4 are each O or NH;
R 1 , R 3 , R 6 , R 8 , R 10 , and R 13 are each —CH 2 CH 2 —;
R 4 , R 5 , R 9 and R 12 are each —CH 2 —;
R 2 , R 7 , R 11 and R 14 are each —(CH2) n —, wherein n is 2, 3, or 4;
L 1 , L 5 , L 7 , L 8 , L 10 , L 12 form an ester;
L 6 , L 9 , L ii , and L 13 form an amide; and
PD ii and PD jj are residues selected from the group consisting of from ferulic acid (FA), isoferulic acid (IFA), syringic acid, and sinapinic acid (SAA).

16. The coating of claim 1 , wherein
L 2 is a residue of a polycaprolactone, a caprolactone, a polylactic acid, a polylactone or a lactic acid or lactone;
L 3 is a residue of polyethylene glycol;
L 4 is a residue of a polycaprolactone, a caprolactone, a polylactic acid, a polylactone or a lactic acid or lactone;
X 1 , X 2 , X 3 and X 4 are each O or NH;
R 3 , R 6 , R 10 , and R 13 are each —CH 2 CH 2 —;
R 1 , R 8 , R 4 , R 5 , R 9 and R 12 are each —CH 2 —;
R 2 , R 7 , R 11 and R 14 are each —(CH2) n —, wherein n is 2 or 3;
L 1 , L 5 , L 7 , L 8 , L 10 , L 12 form an ester;
L 6 , L 9 , L 11 , and L 13 form an amide; and
PD ii and PD jj are residues of ferulic acid or syringic acid.

17. A bioadhesive construct, comprising: a support suitable for tissue repair or reconstruction; and the coating of claim 1 .

18. The bioadhesive construct of claim 17 , wherein said oxidant is formulated with the coating.

19. The bioadhesive construct of claim 17 , wherein said oxidant is applied to said coating.

20. The bioadhesive construct of claim 17 , wherein said support is a film, a mesh, a membrane, a nonwoven or a prosthetic.

21. The bioadhesive construct of claim 17 , comprising:
a) a support suitable for tissue repair or reconstruction;
b1) a first coating comprising a compound comprising the formula (I) and a polymer;
b2) a second coating coated onto said first coating, wherein said second coating comprises a compound comprising the formula (I); and
c) an oxidant comprising tetraethylammonium periodate or tetrapropylammonium periodate.

22. The bioadhesive construct of claim 17 , comprising:
a) a support suitable for tissue repair or reconstruction;
b1) a first coating comprising a compound comprising the formula (I) and a first polymer;
b2) a second coating coated onto said first coating, wherein said second coating comprises a second compound comprising the formula (I) and a second polymer, wherein said first and second polymer may be the same or different, and wherein said first and said second compound comprising the formula (I) can be the same or different; and
c) an oxidant comprising tetraethylammonium periodate or tetrapropylammonium periodate.

23. The bioadhesive construct of claim 17 comprising:
a) a support suitable for tissue repair or reconstruction;
b1) a first coating comprising a first compound comprising the formula (I);
b2) a second coating coated onto said first coating, wherein said second compound comprising the formula (I), wherein said first and second compound comprising the formula (I) can be the same or different; and
c) an oxidant comprising tetraethylammonium periodate or tetrapropylammonium periodate.

24. A bioadhesive construct comprising:
a support suitable for tissue repair or reconstruction; and
the coating of claim 1 , wherein the coating comprises a blend of a polymer and a compound comprising formula (I).

25. The bioadhesive construct of claim 24 , wherein the polymer is present in a range of about 1 to 50 percent by weight.

26. The bioadhesive construct of claim 25 , wherein said polymer is present is present at an amount of about 30 percent by weight.

27. The bioadhesive construct of claim 25 , wherein said oxidant is applied to said coating.

28. The coating of claim 1 , wherein said oxidant is formulated with the coating.

Assignees

• Dsm Ip Assets Bv

Inventors

• Murphy John L
• Dalsin Jeffrey L
• Lyman Arinne N
• Bremer Laura L
• Broussard Joel L
• Winterbottom Neil
• Koepsel Justin T

Classifications

• C08G63/912

  derived from hydroxycarboxylic acids · CPC title

• B32B7/12

  using interposed adhesives or interposed materials with bonding properties · CPC title

• B32B27/34

  comprising polyamides · CPC title

• C09D169/00

  Coating compositions based on polycarbonates; Coating compositions based on derivatives of polycarbonates · CPC title

• B32B2255/02

  on fibrous or filamentary layer · CPC title