Biofouling resistant coatings and methods of making and using the same

A medical device coated with a compound comprising:

• a) a repeating unit of Formula (VII):
• wherein
• each R1a and R1b is independently selected from hydrogen and halogen;
• each R2a and R2b is independently selected from halogen, —CN, and optionally substituted C1-C6 fluoroalkyl;
• each A1 and A2 is independently selected from —C(═O)—, —S(═O)—, —S(═O)2—, and —S(═O)(=NR3c)—;
• each B1 and B2 is independently selected from —O— and —NR3c—;
• Z1 is —(CR6cR6d)s—;
• each R4c, R4d, R5d, R5e, R5c, and R5d is independently selected from hydrogen, halogen, —CN, —OR9a, optionally substituted C1-C4 alkyl, optionally substituted C1-C4 fluoroalkyl,
• optionally substituted C2-C6 alkenyl, —NR3cCR3d, —S(═O)2O−, —S(═O)2OR9a, —C(═O)O−, and —C(═O)OR9a;
• each R3c and R3d is independently selected from hydrogen, optionally substituted C1-C4 alkyl, —X-optionally substituted C1-C4 alkyl, optionally substituted C2-C6 alkenyl, and optionally substituted aryl;
• X is —C(═O)—, —S(═O)—, or —S(═O)2—;
• each R9a, R11a, R11b, and R11c is independently selected from hydrogen, optionally substituted C1-C4 alkyl, and optionally substituted aryl;
• n is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8;
• and
• s is an integer selected from 1, 2, 3, 4, and 5;
• b) a repeating unit of Formula (VIII):
• wherein,
• A3 is —C(═O)—, —S(═O)—, —S(═O)2—, or —S(═O)(=NR3c)—;
• B3 is —O— or —NR3c—;
• D is —S(═O)2O−, —S(═O)2OR9a, —C(═O)O−, or —C(═O)OR9a;
• Z2 is —(CR6cR6d)t—;
• Z3 is —(CR6cR6d)p—;
• each R3a and R3b is independently selected from hydrogen, optionally substituted C1-C4 alkyl, and optionally substituted benzyl;
• each R6c and R6d is independently selected from hydrogen, halogen, —CN, —OR9a, optionally substituted C1-C4 alkyl, optionally substituted C1-C4 fluoroalkyl, optionally substituted C2-C6 alkenyl, —NR3cR3d, —S(═O)2O−, —S(═O)2OR9a, —C(═O)O−, and —C(═O)OR9a;
• each R3c and R3d is independently selected from hydrogen, optionally substituted C1-C4 alkyl, —X-optionally substituted C1-C4 alkyl, optionally substituted C2-C6 alkenyl, and optionally substituted aryl;
• X is —C(═O)—, —S(═O)—, or —S(═O)2—;
• each R9a, R12a, R12b, and R12c is independently selected from hydrogen, optionally substituted C1-C4 alkyl, and optionally substituted aryl;
• t is an integer selected from 1, 2, 3, 4, or 5;
• p is an integer selected from 1, 2, 3, 4, or 5;
• and
• wherein the repeating unit of Formula (VIII) is charged or zwitterionic;
• and
• c) a repeating unit of Formula (IX):
• A4 is —C(═O)—, —S(═O)—, —S(═O)2—, or —S(═O)(=NR3c)—;
• B4 is —O— or —NR3c—;
• Z4 is —(CR6cR6d)k—;
• E is —CN, —OR9a, —NR9aR9b, —NR9aR9bR9c+, optionally substituted C1-C4 alkyl, optionally substituted C1-C6 fluoroalkyl, —S(═O)2O−, —S(═O)2OR9a, —C(═O)O−, or —C(═O)OR9a;
• each R6c, and R6d is independently selected from hydrogen, halogen, —CN, —OR9a, optionally substituted C1-C4 alkyl, optionally substituted C1-C4 fluoroalkyl, optionally substituted C2-C6 alkenyl, —NR3cR3d, —S(═O)2O−, —S(═O)2OR9a, —C(═O)O−, and —C(═O)OR9a;
• each R3c and R3d is independently selected from hydrogen, optionally substituted C1-C4 alkyl, —X-optionally substituted C1-C4 alkyl, optionally substituted C2-C6 alkenyl, and optionally substituted aryl;
• X is —C(═O)—, —S(═O)—, or —S(═O)2—;
• each R9a, R9b, R9c, R13a, R13b, and R13c is independently selected from hydrogen, optionally substituted C1-C4 alkyl, and optionally substituted aryl;
• and
• k is an integer selected from 1, 2, 3, 4, or 5.