Biofouling resistant coatings and methods of making and using the same

Patent metadata

Field	Value
Publication number	US-10729822-B2
Application number	US-201816206596-A
Country	US
Kind code	B2
Filing date	Nov 30, 2018
Priority date	Dec 1, 2017
Publication date	Aug 4, 2020
Grant date	Aug 4, 2020

Abstract

Disclosed herein are compositions to use in biofouling-resistant coatings, biofouling-resistant coatings, methods of making biofouling-resistant coatings, biofouling-resistant devices, and methods of making biofouling-resistant devices.

First claim

What is claimed is:

1. A compound that has the structure of formula (II):

wherein
each R 1a and R 1b is independently selected from hydrogen and halogen;
each R 2a and R 2b is independently selected from halogen, —CN, and optionally substituted C 1 -C 6 fluoroalkyl;
A 1 is —S(═O) 2 —; A 2 is —C(═O)—; and A 3 is —C(═O)—;
each B 1 , B 2 , and B 3 is independently selected from —O— and —NR 3c —;
D is —S(═O) 2 O − , —S(═O) 2 OR 9a , —C(═O)O − , or —C(═O)OR 9a ;
Z 1 is —(CR 6c R 6d ) s —;
Z 2 is —(CR 6c R 6d ) t —;
Z 3 is —(CR 6c R 6d ) p —;
each R 3a and R 3b is independently selected from hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted benzyl;
each R 3c and R 3d is independently selected from hydrogen, optionally substituted C 1 -C 4 alkyl, —X— optionally substituted C 1 -C 4 alkyl, optionally substituted C 2 -C 6 alkenyl, and optionally substituted aryl;
X is —C(═O)—, —S(═O)—, or —S(═O) 2 —;
each R 4c , R 4d , R 5d , R 5e , R 6c , and R 6d is independently selected from hydrogen, halogen, —CN, —OH, optionally substituted C 1 -C 4 alkyl, optionally substituted C 1 -C 4 fluoroalkyl, optionally substituted C 2 -C 6 alkenyl, —NR 3c R 3d , —S(═O) 2 O − , —S(═O) 2 OR 9a , —C(═O)O − , and —C(═O)OR 9a ;
each R 9a , R 11a , R 11b , R 11c , R 12a , R 12b , and R 12c is independently selected from hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted aryl;
n is an integer selected from 0, 1, 2, 3, 4, 5, and 6;
s is an integer selected from 1, 2, 3, 4, or 5;
t is an integer selected from 1, 2, 3, 4, or 5;
p is an integer selected from 1, 2, 3, 4, or 5;
q is an integer greater than or equal to 3 and less than or equal to 60;
r is an integer greater than or equal to 1 and less than or equal to 50; and
wherein the compound of formula (II) is charged or zwitterionic.

2. The compound of claim 1 , wherein each R 1a and R 1b is independently halogen.

3. The compound of claim 1 , wherein each R 2a and R 2b is independently selected from halogen, —CN, and —CF 3 .

4. The compound of claim 1 , wherein B 1 and B 2 are each —NR 3c — and wherein B 3 is —O—.

5. The compound of claim 4 , wherein each R 3c is hydrogen or —CH 3 .

6. The compound of claim 1 , wherein D is —S(═O) 2 O − .

7. The compound of claim 1 , wherein each R 6c and R 6d is hydrogen and wherein each R 3a and R 3b is —CH 3 .

8. The compound of claim 1 , wherein each R 1a , R 1b , R 2a , and R 2b is F.

9. The compound of claim 1 , wherein R 11a is hydrogen or —CH 3 .

10. The compound of claim 1 , wherein q is an integer greater than or equal to 3 and less than 40.

11. The compound of claim 1 , wherein q is an integer greater than or equal to 3 and less than or equal to 50.

12. The compound of claim 1 , wherein r is an integer more than 10 and less than or equal to 50.

13. A medical device coated with a compound that has the structure of formula (II):

wherein
each R 1a and R 1b is independently selected from hydrogen and halogen;
each R 2a and R 2b is independently selected from halogen, —CN, and optionally substituted C 1 -C 6 fluoroalkyl;
each A 1 , A 2 , and A 3 is independently selected from —C(═O)—, —S(═O)—, —S(═O) 2 —, and —S(═O)(═NR 3c )—;
each B 1 , B 2 , and B 3 is independently selected from —O— and —NR 3c —;
D is —S(═O) 2 O − , —S(═O) 2 OR 9a , —C(═O)O − , or —C(═O)OR 9a ;
Z 1 is —(CR 6c R 6d ) s —;
Z 2 is —(CR 6c R 6d ) t —;
Z 3 is —(CR 6c R 6d ) p —;
each R 3a and R 3b is independently selected from hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted benzyl;
each R 3c and R 3d is independently selected from hydrogen, optionally substituted C 1 -C 4 alkyl, —X— optionally substituted C 1 -C 4 alkyl, optionally substituted C 2 -C 6 alkenyl, and optionally substituted aryl;
X is —C(═O)—, —S(═O)—, or —S(═O) 2 —;
each R 4c , R 4d , R 5d , R 5e , R 6c , and R 6d is independently selected from hydrogen, halogen, —CN, —OH, optionally substituted C 1 -C 4 alkyl, optionally substituted C 1 -C 4 fluoroalkyl, optionally substituted C 2 -C 6 alkenyl, —NR 3c R 3d , —S(═O) 2 O − , —S(═O) 2 OR 9a , —C(═O)O − , and —C(═O)OR 9a ;
each R 9a , R 11a , R 11b , R 11c , R 12a , R 12b , and R 12c is independently selected from hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted aryl;
n is an integer selected from 0, 1, 2, 3, 4, 5, and 6;
s is an integer selected from 1, 2, 3, 4, or 5;
t is an integer selected from 1, 2, 3, 4, or 5;
p is an integer selected from 1, 2, 3, 4, or 5;
q is an integer greater than or equal to 3 and less than or equal to 60;
r is an integer greater than or equal to 1 and less than or equal to 50; and
wherein the compound of formula (II) is charged or zwitterionic; and
wherein the medical device is an implantable medical device.

14. The medical device of claim 13 , wherein each R 1a and R 1b is independently halogen.

15. The medical device of claim 13 , wherein each R 2a and R 2b is independently selected from halogen, —CN, and —CF 3 .

16. The medical device of claim 13 , wherein A 1 is —S(═O) 2 —; A 2 is —C(═O)—; and A 3 is —C(═O)—.

17. The medical device of claim 13 , wherein B 1 and B 2 are each —NR 3c — and wherein B 3 is —O—.

18. The medical device of claim 17 , wherein each R 3c is hydrogen or —CH 3 .

19. The medical device of claim 13 , wherein D is —S(═O) 2 O − .

20. The medical device of claim 13 , wherein each R 6c and R 6d is hydrogen and wherein each R 3a and R 3b is —CH 3 .

21. The medical device of claim 13 , wherein each R 1a , R 1b , R 2a , and R 2b is F.

22. The medical device of claim 13 , wherein R 11a is hydrogen or —CH 3 .

23. The medical device of claim 13 , wherein q is an integer greater than or equal to 3 and less than 40.

24. The medical device of claim 13 , wherein q is an integer greater than or equal to 3 and less than or equal to 50.

25. The medical device of claim 13 , wherein r is an integer more than 10 and less than or equal to 50.

26. The medical device of claim 13 , wherein the medical device comprises a tubing.

27. A medical device coated with a compound that has the structure of formula (II):

wherein
each R 1a and R 1b is independently selected from hydrogen and halogen;
each R 2a and R 2b is independently selected from halogen, —CN, and optionally substituted C 1 -C 6 fluoroalkyl;
A 1 is —S(═O) 2 —; A 2 is —C(═O)—; and A 3 is —C(═O)—;
each B 1 , B 2 , and B 3 is independently selected from —O— and —NR 3c —;
D is —S(═O) 2 O − , —S(═O) 2 OR 9a , —C(═O)O − , or —C(═O)OR 9a ;
Z 1 is —(CR 6c R 6d ) s —;
Z 2 is —(CR 6c R 6d ) t —;

Assignees

• Univ California
• Hydrophilix Inc

Inventors

• Kaner Richard B
• Chen Dayong
• Mcverry Brian T
• Rao Ethan
• Polasko Alexandra L

Classifications

• A61L17/005 Primary

  containing a biologically active substance, e.g. a medicament or a biocide · CPC title

• C08F220/387

  and containing nitrogen and oxygen · CPC title

• C08J7/056

  Forming hydrophilic coatings · CPC title

• C08F220/58

  containing oxygen in addition to the carbonamido oxygen {, e.g. N-methylolacrylamide, N-(meth)acryloylmorpholine} · CPC title

• A61L27/54

  Biologically active materials, e.g. therapeutic substances {(A61L27/227 takes precedence)} · CPC title