# US 12,006,395 B2 · Biodegradable polymer

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- Number: US 12,006,395 B2
- Document ID: US12006395B2
- Status: Granted
- Kind: B2
- Application number: 15/540,201
- Filed: 2015-12-31
- Published: 2017-12-28
- Granted: 2024-06-11
- Earliest claimed: 2015-01-02
- Assignees: Yissum Research Development Company of the Hebrew University of Jerusalem
- Applicants: Yissum Research Development Company of the Hebrew University of Jerusalem Ltd
- Inventors: Daniel Cohn
- Web page: https://patentgrep.com/patent/US12006395B2

## CPC

- C08G 18/42: Polycondensates having carboxylic or carbonic ester groups in the main chain
- A61L 15/26: Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives thereof {(A61L15/225 takes precedence)}
- A61L 17/10: containing macromolecular materials
- A61L 17/12: Homopolymers or copolymers of glycolic acid or lactic acid
- A61L 27/18: obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- A61L 27/34: Macromolecular materials
- A61L 31/06: obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds {(A61L31/041 takes precedence)}
- A61L 31/10: Macromolecular materials
- C08G 18/4277: {Caprolactone and/or substituted caprolactone}
- C08G 18/4825: {Polyethers containing two hydroxy groups (C08G18/4833 - C08G18/5096 take precedence)}
- C08G 18/73: acyclic
- C08G 18/74: cyclic
- C08G 18/76: aromatic
- C08G 63/664: derived from hydroxy carboxylic acids
- C08G 63/685: containing nitrogen
- C08G 63/6852: {derived from hydroxy carboxylic acids}
- C08G 63/91: Polymers modified by chemical after-treatment
- C08G 63/912: {derived from hydroxycarboxylic acids}
- A61K 47/34: Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers (A61K47/10 takes precedence)
- C08G 2220/00: Compositions for preparing gels other than hydrogels, aerogels and xerogels
- C08G 2230/00: Compositions for preparing biodegradable polymers
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- A61L: METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES (preservation of bodies or disinfecting characterised by the agents employed A01N; preserving, e.g. sterilising, food or foodstuffs A23; preparations for medical, dental or toiletry purposes A61K)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)

## Abstract

The invention provides a class of polymeric materials being ABA tri-block or AB di-block, comprised of biodegradable segments and poly(propylene oxide) (PPO) segment and uses thereof.

## Claims

### Claim 1

A solid polymer comprising a plurality of ABA tri-blocks, wherein A is a biodegradable segment consisting of poly(caprolactone) (PCL) and B consists of a polypropylene oxide) (PPO) segment, wherein, in the polymer, the tri-blocks are linked to one another via a urethane linkage, which urethane linkage optionally includes a chain extender between urethane groups;
and wherein each tri-block has a molecular weight of between 2 KDa and 5,000 Kda.

### Claim 2 (depends on 1)

A solid polymer according to claim 1 wherein said urethane linkage includes a chain extender between urethane groups.

### Claim 3 (depends on 2)

A solid polymer according to claim 2 wherein said chain extender is bifunctional so as to terminate in two urethane groups.

### Claim 4 (depends on 2)

A solid polymer according to claim 2, wherein said chain extender is multifunctional so as to terminate in at least three urethane groups.

### Claim 5 (depends on 2)

A solid polymer according to claim 2, wherein said chain extender is hexamethylene.

### Claim 6 (depends on 1)

A suture comprising a polymer according to claim 1.

### Claim 7 (depends on 6)

The suture according to claim 6, being a monofilament suture or a multifilament suture.

### Claim 8 (depends on 7)

The suture according to claim 7, being a monofilament suture made of a single strand of the polymer.

### Claim 9 (depends on 7)

The suture according to claim 7, being a multifilament suture formed of a plurality of filaments, each filament being composed of a said polymer of the same or different composition.

### Claim 10 (depends on 6)

The suture according to claim 6, coated with at least one coating material comprising active or non-active materials.

### Claim 11 (depends on 10)

The suture of claim 10, wherein said coating material comprises an active material that is a bioactive agent.

### Claim 12 (depends on 1)

A solid polymer according to claim 1, wherein each said ABA tri-block is a tri-block polymer selected from the group consisting of the polymers numbered 1 to 28 in Table 1:
Polymer
PO/CL
Total # of CL
Mw
Mw tri-
#
PPCA
ratio
units
2*PCL*114
block
1
2000
0.1
340
38,760
40,760
2
(34)
0.2
170
19,380
21,380
3
0.3
113
12,920
14,920
4
0.4
85
9,690
11,690
5
0.5
68
7,752
9,752
6
1.0
34
3,876
5,876
7
2.0
17
1,938
3,938
8
3000
0.1
520
59,280
62,280
9
(52)
0.2
260
29,640
32,640
10
0.3
173
19,760
22,760
11
0.4
130
14,820
17,820
12
0.5
104
11,856
14,856
13
1.0
52
5,928
8,928
14
2.0
26
2,964
5,964
15
4000
0.1
690
78,660
82,660
16
(69)
0.2
345
39,330
43,330
17
0.3
230
26,220
30,220
18
0.4
173
19,665
23,665
19
0.5
138
15,732
19,732
20
1.0
69
7,866
11,866
21
2.0
35
3,933
7,933
22
8000
0.1
1380
157,320
165,320
23
(138)
0.2
690
78,660
86,660
24
0.3
460
52,440
60,440
25
0.4
345
39,330
47,330
26
0.5
276
31,464
39,464
27
1.0
138
15,732
23,732
28
2.0
69
7,866
15,866

### Claim 13 (depends on 1)

A medical device composed of a polymer according to claim 1.

### Claim 14 (depends on 13)

The device according to claim 13, being in a form selected from the group consisting of a film, fiber, filament, mesh, membrane, rod, a coating, textile fabric, a non-woven structure, gel, a medical textile, a medical device, an implant, a prostheses, a wound healing device, a suture, a mesh and a staple.

### Claim 15 (depends on 1)

A suture consisting of a polymer according to claim 1.