US 11,752,212 B2
N-oxide and ectoine monomers, polymers, their compositions, and related methods
Shaoyi Jiang, Redmond, WA (US); Priyesh Jain, Seattle, WA (US); Jinrong Ma, Seattle, WA (US); and Bowen Li, Seattle, WA (US)
Assigned to UNIVERSITY OF WASHINGTON, Seattle, WA (US)
Appl. No. 16/627,068
Filed by University of Washington, Seattle, WA (US)
PCT Filed Jun. 29, 2018, PCT No. PCT/US2018/040448
§ 371(c)(1), (2) Date Dec. 27, 2019,
PCT Pub. No. WO2019/006398, PCT Pub. Date Jan. 3, 2019.
Claims priority of provisional application 62/526,591, filed on Jun. 29, 2017.
Prior Publication US 2020/0123294 A1, Apr. 23, 2020
Int. Cl. A61K 47/58 (2017.01); A61K 9/51 (2006.01); A61L 27/34 (2006.01); A61L 29/08 (2006.01); A61L 31/10 (2006.01); C08F 220/60 (2006.01); C08J 3/075 (2006.01); C09D 5/16 (2006.01); C12N 5/078 (2010.01); C08F 222/22 (2006.01)
CPC A61K 47/58 (2017.08) [A61K 9/5138 (2013.01); A61L 27/34 (2013.01); A61L 29/085 (2013.01); A61L 31/10 (2013.01); C08F 220/60 (2013.01); C08J 3/075 (2013.01); C09D 5/16 (2013.01); C12N 5/0644 (2013.01); C08F 220/603 (2020.02); C08F 222/225 (2020.02); C08J 2300/206 (2013.01); C08J 2333/26 (2013.01)] 12 Claims
 
1. A substrate surface coated with a layer of one or more N-oxide polymers or one or more N-oxide copolymers, wherein the N-oxide polymer or N-oxide copolymer has repeating units of formula (IV) or (V):

OG Complex Work Unit Chemistry
wherein
indicates the point of attachment of the repeating unit to other repeating units in the polymer or copolymer;
R1 is selected from the group consisting of hydrogen, fluorine, trifluoromethyl, cyano, C1-C20 alkyl, and C6-C12 aryl;
R2 and R3 are independently selected from functional groups suitable for polymerization by addition, condensation or free radical polymerization;
R4 and R5 are independently selected from the group consisting of hydrogen, C1-C20 alkyl, and C6-C12 aryl, cyclic alkyl;
L is C or Si;
L2 is independently selected from —(CH2)x— or —(CH(CN))x—, where x is an integer from 1 to 20; and
L3 and L4 are independently selected from —(CH2)—, —(CH(CN))x—, —C(═O)NH(CH2)x—, —C(═O)O(CH2)x—, —C(═O)OC(═O)O(CH2)x—, —(CH2)x—O—(CH2)x—, and —(CH2)x—S—S—(CH2)x—, where x at each occurrence is an integer independently selected from 1 to 20; and
n is an integer from about 10 to about 500,
wherein the substrate is a biomedical device selected from the group consisting of catheters, ear drainage tubes, feeding tubes, glaucoma drainage tubes, hydrocephalous shunts, keratoprosthesis, nerve guidance tubes, tissue adhesives, x-ray guides, artificial joints, artificial heart valves, artificial blood vessels, pacemakers, left ventricular assist devices (LVAD), artery grafts, vascular grafts, stents, intravascular stents, cardiac valves, joint replacements, blood vessel prostheses, skin repair devices, cochlear replacements, contact lenses, artificial ligaments and tendons, dental implants, and tissue scaffolds for regenerative tissue engineering.