IP Library Granted Patent US 12,364,710
Granted Patent B2
US 12,364,710 · App. 17/856,198 · Granted Jul 22, 2025

Lubricating block copolymers and their use as biomimetic boundary lubricants

Inventors: David Putnam (Ithaca, NY); Lawrence Bonassar (Ithaca, NY); Zhexun Sun (Ithaca, NY)
Assignee: CORNELL UNIVERSITY
A61K31/785A61K31/795C08F220/286C08F293/005C08F2438/03
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 12,364,710
App. No.
17/856,198
Granted
Jul 22, 2025
Kind
B2
Abstract

The invention relates to methods of lubricating biological tissue, such as joints, bone, ocular tissue, nasal tissue, tendons, tendon capsule, and vaginal tissue, by contacting the biological tissue with an effective amount of a block copolymer lubricating composition which functions at least or better than lubricin. In particular embodiments, the method is used to treat osteoarthritis. In specific embodiments, the block copolymer has an ammonium-containing polymer block and a non-ionic hydrophilic polymer block, or the copolymer has a carboxylic acid-containing polymer block and a non-acid non-ionic hydrophilic polymer block.

Claims (29)

1. A block copolymer having the following structure:

wherein:

X is selected from —NR′—, —O—, and a bond, wherein R′ is selected from hydrogen atom and hydrocarbon groups having at least one and up to six carbon atoms;

Y is selected from polyalkylene glycol, saccharide, and polyalcohol;

R is a cartilage binding domain;

subscripts d and e are independently integers of at least 3; and

subscript f is 0 or an integer of at least 1;

wherein the hydrogen atom on the shown carboxylic acid group is optionally replaced with a positively charged metal ion or positively charged organic group; and

wherein, by the laws of chemistry, the block copolymer is terminated on the end opposite to the thiol group by a terminal group.

2. The block copolymer of claim 1 , wherein Y is a saccharide.

3. The block copolymer of claim 2 , wherein said saccharide is a monosaccharide or polysaccharide.

4. A block copolymer having the following structure:

wherein:

X is selected from —NR′—, —O—, and a bond, wherein R′ is selected from hydrogen atom and hydrocarbon groups having at least one and up to six carbon atoms;

Y is selected from saccharides and sugar alcohols;

R is a hydrogen atom, hydrocarbon group having 1-12 carbon atoms, or a cartilage binding domain;

subscripts d and e are independently integers of at least 3; and

subscript f is 0 or an integer of at least 1;

wherein the hydrogen atom on the shown carboxylic acid group is optionally replaced with a positively charged metal ion or positively charged organic group; and

wherein, by the laws of chemistry, the block copolymer is terminated on the end opposite to the thiol group by a terminal group.

5. A method for imparting a suitable level of lubricity to a biological tissue, the method comprising contacting said biological tissue with a sufficient amount of a composition to impart suitable lubricity, said composition comprising a block copolymer having the following structure:

X is selected from —NR′— and —O—, wherein R′ is selected from hydrogen atom and hydrocarbon groups having at least one and up to six carbon atoms;

Y is selected from polyalkylene glycol, saccharide, and polyalcohol;

R is a cartilage binding domain;

subscripts d and e are independently integers of at least 3; and

subscript f is 0 or an integer of at least 1;

wherein the hydrogen atom on the shown carboxylic acid group is optionally replaced with a positively charged metal ion or positively charged organic group; and

wherein, by the laws of chemistry, the block copolymer is terminated on the end opposite to the thiol group by a terminal group.

6. The method of claim 5 , wherein said biological tissue is selected from joints, bone, ocular tissue, nasal tissue, tendons, tendon capsule, and vaginal tissue.

Continuity (3)
Continuation 16339474
Provisional Application 62403962 · Oct 4, 2016
Related Publication 20230210892A1 · Jul 6, 2023
References Cited (27)
US 3110615A · Keel · 1963 [cited by examiner]
US 6024954A · Park et al. · 2000 [cited by applicant]
US 10344243B2 · Putnam et al. · 2019 [cited by applicant]
US 20040033984A1 · Muller · 2004 [cited by examiner]
US 20090018270A1 · Crooks · 2009 [cited by examiner]
US 20140051771A1 · Hufen et al. · 2014 [cited by applicant]
CN 101035573A · 2007 [cited by applicant]
CN 104870020A · 2015 [cited by applicant]
CN 105073155B · 2018 [cited by applicant]
CN 110050003A · 2019 [cited by applicant]
JP 2010134419A · 2010 [cited by applicant]
WO 2002077075A1 · 2002 [cited by applicant]
WO 2008130604A2 · 2008 [cited by applicant]
WO 2014063102A1 · 2014 [cited by applicant]
WO 2015054452A1 · 2015 [cited by applicant]
WO 2015144886A1 · 2015 [cited by applicant]
WO 2016014408A1 · 2016 [cited by applicant]
Notice of Reasons for Rejection dated May 16, 2023 received in Japanese Patent Application No. 2022-062729, 7 pages. [cited by applicant]
European Office Action dated Jan. 11, 2023 received in European Patent Application No. 17 859 078.2. [cited by applicant]
Extended Supplementary European Search Report dated May 8, 2020 received in European Patent Application No. 17 859 078.2. [cited by applicant]
Hernandez-Barajas, J., et al., “Inverse-emulsion copolymerization of acrylamide and quaternary ammonium cationic monomers with block copolymeric surfactants: copolymer composition control using batch and semi-batch tech… [cited by applicant]
Jacquin, M., et al., “Characterization of Amphiphilic Diblock Copolymers Synthesized by MADIX Polymerization Process”, Macromolecules, 2007, pp. 2672-2682, vol. 40. [cited by applicant]
Loiseau, J., et al., “Synthesis and Characterization of Poly(acrylic acid) Produced by RAFT Polymerization. Application as a Very Efficient Dispersant of CaCO3, Kaolin, and TiO2”, Macromolecules, 2003, pp. 3066-3077, 36. [cited by applicant]
Notice of Reason(s) for Rejection dated Oct. 5, 2021 received in Japanese Patent Application No. 2019-518233. [cited by applicant]
Wang, A., et al. “POEGMA-b-PAA comb-like polymer dispersant for A12 suspensions”, Journal of Applied Polymer Science, Jan. 9, 2016, 15 pages, vol. 133, Issue 17. [cited by applicant]
Willcock, H., et al., “End group removal and modification of RAFT polymers”, Polymer Chemistry 2010, Accepted Nov. 27, 2009, First published as an Advance article on the web Dec. 23, 2009, pp. 149-157, 1. [cited by applicant]
Chinese Office Action dated Mar. 20, 2024 issued in Chinese Application No. 202210792713.0, 21 pages. [cited by applicant]