Medical device and method for manufacturing same

Patent metadata

Field	Value
Publication number	US-12054564-B2
Application number	US-202217674891-A
Country	US
Kind code	B2
Filing date	Feb 18, 2022
Priority date	Aug 21, 2019
Publication date	Aug 6, 2024
Grant date	Aug 6, 2024

Abstract

A medical device includes: a substrate layer; an adhesive layer on at least a part of the substrate layer and containing a hydrophilic copolymer (1) containing a structural unit derived from a polymerizable monomer (A) having a sulfobetaine structure, a structural unit derived from a polymerizable monomer (B) having at least one group selected from the group consisting of a sulfonic acid group (—SO3H), a sulfuric acid group (—OSO3H), a sulfurous acid group (—OSO2H), and salt groups thereof, and a structural unit derived from a polymerizable monomer (C) having a photoreactive group; and a surface lubricious layer formed on at least a part of the adhesive layer and containing a hyaluronic acid or a salt thereof and a hydrophilic copolymer (2).

First claim

What is claimed is:

1. A medical device, comprising:
a substrate layer;
an adhesive layer formed on at least a part of the substrate layer, the adhesive layer containing: a hydrophilic copolymer (1) containing (i) a structural unit derived from a polymerizable monomer (A) having a sulfobetaine structure, (ii) a structural unit derived from a polymerizable monomer (B) having at least one group selected from the group consisting of a sulfonic acid group, a sulfuric acid group, a sulfurous acid group, and salt groups thereof, and (iii) a structural unit derived from a polymerizable monomer (C) having a photoreactive group; and
a surface lubricious layer formed on at least a part of the adhesive layer, the surface lubricious layer containing a hyaluronic acid or a salt thereof and a hydrophilic copolymer (2) containing (i) a structural unit derived from a polymerizable monomer (A′) having a sulfobetaine structure, (ii) a structural unit derived from a polymerizable monomer (B′) having at least one group selected from the group consisting of a sulfonic acid group, a sulfuric acid group, a sulfurous acid group, and salt groups thereof, and (iii) a structural unit derived from a polymerizable monomer (C′) having a photoreactive group.

2. The medical device according to claim 1 , wherein
the hydrophilic copolymer (2) is contained in the surface lubricious layer at a ratio of more than 5 parts by weight and less than 500 parts by weight with respect to 1 part by weight of the hyaluronic acid or a salt thereof.

3. The medical device according to claim 1 , wherein
the polymerizable monomer (A) and/or (A′) is represented by the following formula (1):

wherein in the above formula (1),
R 11 represents a hydrogen atom or a methyl group,
Z 1 represents an oxygen atom or —NH—,
R 12 and R 15 each independently represent a linear or branched alkylene group having 1 to 20 carbon atoms, and
R 13 and R 14 each independently represent a linear or branched alkyl group having 1 to 20 carbon atoms.

4. The medical device according to claim 1 , wherein
the polymerizable monomer (B) and/or (B′) is represented by the following formula (2), (3), or (4):

wherein in the above formula (2),
R 21 represents a hydrogen atom or a methyl group,
Z 2 represents an oxygen atom or —NH—,
R 22 represents a linear or branched alkylene group having 1 to 20 carbon atoms, and
X represents a group selected from the group consisting of a sulfonic acid group, a sulfuric acid group, a sulfurous acid group, and salt groups thereof;

wherein in the above formula (3),
R 31 represents a hydrogen atom or a methyl group,
R 32 represents a single bond or a linear or branched alkylene group having 1 to 20 carbon atoms, and
X represents a group selected from the group consisting of a sulfonic acid group, a sulfuric acid group, a sulfurous acid group, and salt groups thereof; and

wherein in the above formula (4),
R 41 represents a hydrogen atom or a methyl group,
R 42 represents a linear or branched alkylene group having 1 to 20 carbon atoms, and
X represents a group selected from the group consisting of a sulfonic acid group, a sulfuric acid group, a sulfurous acid group, and salt groups thereof.

5. The medical device according to claim 1 , wherein
the polymerizable monomer (C) and/or (C′) has a group having a benzophenone structure.

6. The medical device according to claim 1 , wherein
(a) the polymerizable monomer (A) and/or (A′) is represented by the following formula (1):

wherein in the above formula (1),
R 11 represents a hydrogen atom or a methyl group,
Z 1 represents an oxygen atom or —NH—,
R 12 and R 15 each independently represent a linear or branched alkylene group having 1 to 20 carbon atoms, and
R 13 and R 14 each independently represent a linear or branched alkyl group having 1 to 20 carbon atoms;
(b) the polymerizable monomer (B) and/or (B′) is represented by the following formula (2), (3), or (4):

wherein in the above formula (2),
R 21 represents a hydrogen atom or a methyl group,
Z 2 represents an oxygen atom or —NH—,
R 22 represents a linear or branched alkylene group having 1 to 20 carbon atoms, and
X represents a group selected from the group consisting of a sulfonic acid group, a sulfuric acid group, a sulfurous acid group, and salt groups thereof;

wherein in the above formula (3),
R 31 represents a hydrogen atom or a methyl group,
R 32 represents a single bond or a linear or branched alkylene group having 1 to 20 carbon atoms, and
X represents a group selected from the group consisting of a sulfonic acid group, a sulfuric acid group, a sulfurous acid group, and salt groups thereof; and

wherein in the above formula (4),
R 41 represents a hydrogen atom or a methyl group,
R 42 represents a linear or branched alkylene group having 1 to 20 carbon atoms, and
X represents a group selected from the group consisting of a sulfonic acid group, a sulfuric acid group, a sulfurous acid group, and salt groups thereof; and
(c) the polymerizable monomer (C) and/or (C′) has a group having a benzophenone structure.

7. The medical device according to claim 1 , wherein
the hydrophilic copolymer (1) and the hydrophilic copolymer (2) have the same structure.

8. The medical device according to claim 1 , wherein
the medical device is a catheter, a stent, or a guide wire.

9. A method for manufacturing the medical device according to claim 1 , comprising:
coating a coating liquid (1) containing the hydrophilic copolymer (1) onto the substrate layer to form the adhesive layer; and
coating a coating liquid (2) containing the hyaluronic acid or a salt thereof and the hydrophilic copolymer (2) onto the adhesive layer to form the surface lubricious layer.

10. The method according to claim 9 , wherein
a concentration of the hydrophilic copolymer (2) in the coating liquid (2) is 0.1 wt % to 4.5 wt %.

11. A method for manufacturing the medical device according to claim 5 , comprising:
coating a coating liquid (1) containing the hydrophilic copolymer (1) onto the substrate layer to form the adhesive layer;
irradiating the adhesive layer with active energy rays; and
coating a coating liquid (2) containing the hyaluronic acid or a salt thereof and the hydrophilic copolymer (2) onto the adhesive layer to form the surface lubricious layer.

12. A medical device, comprising:
a substrate layer;
an adhesive layer formed on at least a part of the substrate layer, the adhesive layer containing a hydrophilic copolymer (1) containing (i) a

Assignees

• Terumo Corp

Inventors

• Kuramoto Masanori
• Yokote Narumi

Classifications

• A61M25/0009

  Making of catheters or other medical or surgical tubes · CPC title

• A61L2400/10

  Materials for lubricating medical devices · CPC title

• A61L31/14

  Materials characterised by their function or physical properties {, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials} · CPC title

• A61L31/06

  obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds {(A61L31/041 takes precedence)} · CPC title

• A61L31/048

  obtained by reactions only involving carbon-to-carbon unsaturated bonds (A61L31/041 takes precedence) · CPC title