# US 10,501,575 B2 · Biomimetic fluoroscopic films

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 10,501,575 B2
- Document ID: US10501575B2
- Status: Granted
- Kind: B2
- Application number: 15/573,892
- Filed: 2016-05-26
- Published: 2018-10-11
- Granted: 2019-12-10
- Earliest claimed: 2015-05-26
- Assignees: Board of Regents, The University of Texas System
- Applicants: The Board of Regents of the University of Texas System
- Inventors: Tre Raymond Welch; Amy Claire Kauffman
- Web page: https://patentgrep.com/patent/US10501575B2

## CPC

- C08G 63/6858: {Polycarboxylic acids and polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation}
- A61K 31/573: substituted in position 21, e.g. cortisone, dexamethasone, prednisone or aldosterone
- A61K 47/6935: {the polymer being obtained otherwise than by reactions involving carbon to carbon unsaturated bonds, e.g. polyesters, polyamides or polyglycerol}
- A61L 27/18: obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- A61L 27/50: Materials characterised by their function or physical properties {, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials}
- A61L 27/54: Biologically active materials, e.g. therapeutic substances {(A61L27/227 takes precedence)}
- A61L 27/58: Materials at least partially resorbable by the body
- A61L 31/06: obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds {(A61L31/041 takes precedence)}
- A61L 31/148: {Materials at least partially resorbable by the body}
- A61L 31/16: Biologically active materials, e.g. therapeutic substances {(A61L31/047 takes precedence)}
- A61L 31/18: Materials at least partially X-ray or laser opaque
- C08G 63/826: {Metals not provided for in groups C08G63/83 - C08G63/86 (C08G63/823 takes precedence)}
- C08G 63/87: Non-metals or inter-compounds thereof (boron C08G63/84)
- C08J 5/18: Manufacture of films or sheets
- A61L 2300/426: Immunomodulating agents, i.e. cytokines, interleukins, interferons
- C08J 2367/06: Unsaturated polyesters
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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)
- 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)
- C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29)

## Abstract

Disclosed are biomimetic imageable polymeric materials that include a polymer or copolymer and a covalently-linked contrasting agent where the disclosed films are both bioresorbable and visible by X-ray fluoroscopic imaging and/or magnetic resonance imaging. The invention also provides methods of preparing the polymeric materials and their use in and as implantable medical devices.

## Claims

### Claim 1

A compound having a general structure of (I):
wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, and R11 are each, individually, a hydrogen atom or an alkyl group;
n is 1 to 4, preferably 2;
m is 0 through 5, preferably 1; and
M is a transition, lanthanide, or actinide ion.

### Claim 2 (depends on 1)

The compound of claim 1, wherein R1 and R11 are methyl, and R2, R3, R4, R5, R6, R7, R8, R9, R10, and R12 are hydrogen.

### Claim 3 (depends on 1)

The compound of claim 1, wherein m is 1.

### Claim 4 (depends on 1)

The compound of claim 1, wherein M is gadolinium.

### Claim 5 (depends on 1)

The compound of claim 1, comprising a monomer where n is 1.

### Claim 6 (depends on 1)

The compound of claim 1, wherein the compound is bioresorbable.

### Claim 7 (depends on 1)

The compound of claim 1, wherein the compound emits fluorescent X-rays under electromagnetic radiation, emits electromagnetic radiation waves under an oscillating magnetic field, or both.

### Claim 8 (depends on 1)

The compound of claim 1, wherein the compound is a film.

### Claim 9 (depends on 1)

The compound of claim 1, wherein the compound is:

### Claim 10 (depends on 1)

A method to prepare the compound of claim 1, the method comprising:
(a) obtaining a dialkyl alkylenedioic acid, a 1,2-diol, anhydrous gadodiamide, and a Lewis acid catalyst or Lewis base catalyst; and
(b) reacting the dialkyl alkylenedioic acid, the 1,2-diol, gadodiamide and the Lewis acid catalyst or Lewis base catalyst under conditions sufficient to produce the polymer.

### Claim 11 (depends on 10)

The method of claim 10, wherein the dialkyl alkylenedioic acid and the 1,2-diol of are diethyl fumarate and propylene glycol.

### Claim 12 (depends on 10)

The method of claim 10, wherein the Lewis acid is zinc chloride or the Lewis base is ciprofloxacin.

### Claim 13 (depends on 10)

The method of claim 10, wherein the conditions comprise a temperature of 150° C. to 200° C., preferably 170° C. to 190° C., most preferably 180° C., a pressure of 1 to 5 mmHg, preferably 1 to 2 mmHg, most preferably 1 mmHg with vigorous agitation.

### Claim 14 (depends on 13)

The method of claim 13, wherein the vigorous agitation comprises stirring at 200 to 300 rpm, 210 to 300 rpm, or 220 rpm.

### Claim 15 (depends on 10)

The method of claim 10, wherein a molar ratio of Lewis acid or Lewis base to dialkyl alkylenedioic acid is 0.0004:1 to 0.06:1, preferably 0.02:1.

### Claim 16 (depends on 10)

The method of claim 10, wherein a molar ratio of dialkyl alkylenedioic acid to 1,2-diol is 1:2 to 1:5, preferably 1:3.

### Claim 17 (depends on 10)

The method of claim 10, wherein a molar ratio of gadodiamide to dialkyl alkylenedioic acid is 0.003:1 to 0.06:1, preferably 0.02:1.

### Claim 18 (depends on 10)

The method of claim 10, wherein the conditions further comprise terminating the reaction when the molecular weight of the polymer is 500 Da to 1500 Da, preferably about 1000 Da.