IP Library Granted Patent US 11,376,276
Granted Patent B2
US 11,376,276 · App. 16/339,474 · Granted Jul 5, 2022

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 11,376,276
App. No.
16/339,474
Granted
Jul 5, 2022
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 (36)

1. A block copolymer having the following structure:

wherein:

R 1 , R 2 , and R 3 are independently selected from hydrocarbon groups having at least one and up to twelve carbon atoms;

X and X′ are independently 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 a polyalkylene glycol;

subscript a is an integer in a range of 3-40;

subscript b is an integer in a range of 30-500; and

subscript c is an integer of at least 1;

wherein, by the laws of chemistry, the block copolymer is terminated on each end by terminal groups, and the total positive charge of quaternary ammonium groups in the copolymer is counterbalanced by a total negative charge of equivalent magnitude provided by anions associated with said ammonium groups.

2. The block copolymer of claim 1 , wherein said polyalkylene glycol is polyethylene glycol.

3. The block copolymer of claim 1 , wherein said polyalkylene glycol is constructed of at least two and up to 500 monomer units.

4. The block copolymer of claim 1 , wherein said polyalkylene glycol is constructed of at least two and up to 200 monomer units.

5. The block copolymer of claim 1 , wherein said polyalkylene glycol is constructed of at least two and up to 100 monomer units.

6. The block copolymer of claim 1 , wherein said polyalkylene glycol is constructed of at least two and up to 20 monomer units.

7. The block copolymer of claim 1 , wherein R 1 , R 2 , and R 3 are independently selected from alkyl groups having at least one and up to twelve carbon atoms.

8. The block copolymer of claim 1 , wherein at least one of said terminal groups is a thiol group.

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

wherein:

R 1 , R 2 , and R 3 are independently selected from hydrocarbon groups having at least one and up to twelve carbon atoms;

X and X′ are independently 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 a polyalkylene glycol;

subscript a is an integer in a range of 3-40;

subscript b is an integer in a range of 30-500; and

subscript c is an integer of at least 1;

wherein, by the laws of chemistry, the block copolymer is terminated on each end by terminal groups, and the total positive charge of quaternary ammonium groups in the copolymer is counterbalanced by a total negative charge of equivalent magnitude provided by anions associated with said ammonium groups.

10. The method of claim 9 , wherein at least one of said terminal groups is a thiol group.

11. The method of claim 9 , wherein said biological tissue is selected from joints, bone, ocular tissue, nasal tissue, tendons, tendon capsule, and vaginal tissue.

12. A block copolymer having the following structure:

wherein:

R 1 , R 2 , and R 3 are independently selected from hydrocarbon groups having at least one and up to twelve carbon atoms;

X and X′ are independently 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;

subscript a is an integer in a range of 3-40;

subscript b is an integer in a range of 30-500; and

subscript c is an integer of at least 1;

wherein, by the laws of chemistry, the block copolymer is terminated on each end by terminal groups, wherein at least one of said terminal groups is a thiol group, and the total positive charge of quaternary ammonium groups in the copolymer is counterbalanced by a total negative charge of equivalent magnitude provided by anions associated with said ammonium groups.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 12, 2019
From: PUTNAM, DAVID A.; BONASSAR, LAWRENCE; SUN, ZHEXUN
To: CORNELL UNIVERSITY
Reel/Frame 049733/0221 →
Continuity (2)
Provisional Application 62403962 · Oct 4, 2016
Related Publication 20190231811A1 · Aug 1, 2019