# US 2013/0157930 A1 · Linear polyesteramides from aminophenolic esters

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- Number: US 2013/0157930 A1
- Document ID: US20130157930A1
- Status: Published application
- Kind: A1
- Application number: 13/766,136
- Filed: 2013-02-13
- Published: 2013-06-20
- Earliest claimed: 2008-09-22
- Assignees: TYRX, Inc.
- Inventors: Arthur Schwartz; Satish Pulapura; Sarita Nethula; Archana Rajaram; Arikha Moses
- Web page: https://patentgrep.com/patent/US20130157930A1

## CPC

- C08G 69/44: Polyester-amides
- A61K 9/0024: {Solid, semi-solid or solidifying implants, which are implanted or injected in body tissue (compositions for intravenous administration, normal injectable solutions or dispersions for, e.g. subcutaneous administration A61K9/0019; brain implants A61K9/0085; (coated) prostheses, catheters or stents A61L)}
- A61K 31/09: having two or more such linkages
- A61K 31/4465: only substituted in position 4
- A61K 31/496: Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
- A61K 31/65: Tetracyclines
- A61K 31/7036: having at least one amino group directly attached to the carbocyclic ring, e.g. streptomycin, gentamycin, amikacin, validamycin, fortimicins
- 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)
- A61L 29/06: obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- A61L 29/085: {Macromolecular materials}
- A61L 29/148: {Materials at least partially resorbable by the body}
- A61L 29/16: Biologically active materials, e.g. therapeutic substances {(A61L29/048 takes precedence)}
- A61L 31/06: obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds {(A61L31/041 takes precedence)}
- A61L 31/10: Macromolecular materials
- 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)}
- A61P 31/04: Antibacterial agents
- C08G 69/00: Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule (products obtained from isocyanates or isothiocyanates C08G18/00; polyamide-imides C08G73/14)
- C08L 77/12: Polyester-amides
- C08L 101/00: Compositions of unspecified macromolecular compounds
- A61L 2300/404: Biocides, antimicrobial agents, antiseptic agents
- A61L 2300/802: Additives, excipients, e.g. cyclodextrins, fatty acids, surfactants
- A61L 2400/18: Modification of implant surfaces in order to improve biocompatibility, cell growth, fixation of biomolecules, e.g. plasma treatment
- A61L 2420/06: Coatings containing a mixture of two or more compounds
- A61M 2025/0057: {Catheters delivering medicament other than through a conventional lumen, e.g. porous walls or hydrogel coatings}
- 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)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- A61M: DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY (introducing media into or onto the bodies of animals A61D7/00; means for inserting tampons A61F13/26; devices for administering food or medicines orally A61J; containers for collecting, storing or administering blood or medical fluids A61J1/05); DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY (surgery A61B; chemical aspects of surgical articles A61L); DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR {(Electrotherapy, e.g. producing anaesthesia by the use of alternating or intermittent currents A61N1/36021)}

## Abstract

The present invention is directed to linear, biodegradable polyesteramide (PEA) polymers synthesized with repeating units derived from aminophenol esters and diacids. These PEAs have a monomer repeat represented by as well as a variety of uses to coat, form or comprise medical devices, combination medical devices and pharmaceutical compositions, including sustained release formulations.

## Claims

### Claim 1

A synthetic polymer comprising monomer units represented by the formula:
wherein R is —(CR3R4)a— or —CR3═CR4—;
R1 is hydrogen; saturated or unsaturated alkyl, aryl, alkylaryl or alkyl ether having from 1 to 20 carbon atoms; or —(R5)qO((CR3R4)rO)s—R6;
each R2 is independently a divalent, linear or branched, substituted or unsubstituted alkylene, alkenylene, alkynylene, arylene, alkylarylene, divalent alkyl ether or aryl ether moiety having from 1 to 30 carbon atoms; —(R5)qO((CR3R4)rO)s(R5)q—; or —(R5)qCO2((CR3R4)rO)sCO(R5)q—;
R3 and R4 are each independently, hydrogen or linear or branched, substituted or unsubstituted alkyl having from 1 to 10 carbon atoms,
R5 is independently linear or branched lower alkylene or lower alkenylene;
R6 is independently linear or branched, substituted or unsubstituted, saturated or unsaturated lower alkyl;
the aromatic ring has from zero to four Z1 substituents, each of which is independently selected from the group consisting of halide, lower alkyl, alkoxy, nitro, alkyl ether, a protected hydroxyl group, a protected amino group and a protected carboxylic acid group;
Y is
a is 0, or 2 to 10;
each q is independently 1 to 4; each r is independently 1 to 4; and
each s is independently 1 to 5000.

### Claim 2

A synthetic polymer comprising monomer units represented by the formula:
wherein R is —(CR3R4)a— or —CR3═CR4—;
R1 is hydrogen; saturated or unsaturated alkyl, aryl, alkylaryl or alkyl ether having from 1 to 20 carbon atoms; or —(R5)qO((CR3R4)rO)s—R6;
each R2 is independently a divalent, linear or branched, substituted or unsubstituted alkylene, alkenylene, alkynylene, arylene, alkylarylene, divalent alkyl ether or aryl ether moiety having from 1 to 30 carbon atoms; —(R5)qO((CR3R4)rO)s(R5)q—; or —(R5)qCO2((CR3R4)rO)sCO(R5)q—;
R3 and R4 are each independently, hydrogen or linear or branched, substituted or unsubstituted alkyl having from 1 to 10 carbon atoms,
R5 is independently linear or branched lower alkylene or lower alkenylene;
R6 is independently linear or branched, substituted or unsubstituted, saturated or unsaturated lower alkyl;
the aromatic ring has from zero to four Z1 substituents, each of which is independently selected from the group consisting of halide, lower alkyl, alkoxy, nitro, alkyl ether, a protected hydroxyl group, a protected amino group and a protected carboxylic acid group;
Y is
a is 0 to 10;
each q is independently 1 to 4; each r is independently 1 to 4; and
each s is independently 1 to 5000.

### Claim 3 (depends on 2)

A pharmaceutical composition comprising the polymer of claim 2 and one or more drugs.

### Claim 4 (depends on 3)

The pharmaceutical composition of claim 3, wherein said one or more drugs are selected from the group consisting of antimicrobial agents, antibacterial agents, anesthetics, anti-inflammatory agents, anti-scarring agents, anti-fibrotic agents, leukotriene inhibitors, chemotherapeutic agents.

### Claim 5 (depends on 4)

The pharmaceutical composition of claim 4, wherein said one or more drugs is an antimicrobial agent selected from the group consisting of rifampin, minocycline, gentamicin, vancomycin, triclosan, and combinations thereof.

### Claim 6

A synthetic polymer comprising monomer units represented by the formula:
wherein R is —(CR3R4)a— or —CR3═CR4—;
R1 is hydrogen; saturated or unsaturated alkyl, aryl, alkylaryl or alkyl ether having from 1 to 20 carbon atoms; or —(R5)qO((CR3R4)rO)s—R6;
each R2 is independently a divalent, linear or branched, substituted or unsubstituted alkylene, alkenylene, alkynylene, arylene, alkylarylene, divalent alkyl ether or aryl ether moiety having from 1 to 30 carbon atoms; —(R5)qO((CR3R4)rO)s(R5)q—; or —(R5)qCO2((CR3R4)rO)sCO(R5)q—;
R3 and R4 are each independently, hydrogen or linear or branched, substituted or unsubstituted alkyl having from 1 to 10 carbon atoms,
R5 is independently linear or branched lower alkylene or lower alkenylene;
R6 is independently linear or branched, substituted or unsubstituted, saturated or unsaturated lower alkyl;
the aromatic ring has from zero to four Z1 substituents, each of which is independently selected from the group consisting of halide, lower alkyl, alkoxy, nitro, alkyl ether, a protected hydroxyl group, a protected amino group and a protected carboxylic acid group;
Y is
a is 0 to 10;
each q is independently 1 to 4; each r is independently 1 to 4;
each s is independently 1 to 5000; and
wherein said repeat units are strictly alternating of the form (a)n.