IP Library Granted Patent US 8,952,106
Granted Patent B2
US 8,952,106 · App. 13/766,136 · Granted Feb 10, 2015

Linear polyesteramides from aminophenolic esters

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Quick Facts
Patent No.
US 8,952,106
App. No.
13/766,136
Granted
Feb 10, 2015
Kind
B2
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 (46)

1. A synthetic polymer comprising monomer units represented by the formula:

wherein R is —(CR 3 R 4 ) a — or —CR 3 ═CR 4 —;

R 1 is hydrogen; saturated or unsaturated alkyl, aryl, alkylaryl or alkyl ether having from 1 to 20 carbon atoms; or —(R 5 ) q O((CR 3 R 4 ) r O) s —R 6 ;

each R 2 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; —(R 5 ) q O((CR 3 R 4 ) r O) s (R 5 ) q —; or —(R 5 ) q CO 2 ((CR 3 R 4 ) r O) s CO(R 5 ) q —;

R 3 and R 4 are each independently, hydrogen or linear or branched, substituted or unsubstituted alkyl having from 1 to 10 carbon atoms,

R 5 is independently linear or branched lower alkylene or lower alkenylene;

R 6 is independently linear or branched, substituted or unsubstituted, saturated or unsaturated lower alkyl;

the aromatic ring has from zero to four Z 1 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.

2. A synthetic polymer comprising monomer units represented by the formula:

wherein R is —(CR 3 R 4 ) a — or —CR3═CR4-;

R 1 is hydrogen; saturated or unsaturated alkyl, aryl, alkylaryl or alkyl ether having from 1 to 20 carbon atoms; or —(R 5 ) q O((CR 3 R 4 ) r O) s —R 6 ;

each R 2 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; —(R 5 ) q O((CR 3 R 4 ) r O) s (R 5 ) q —; or —(R 5 ) q CO 2 ((CR 3 R 4 ) r O) s CO(R 5 ) q —;

R 3 and R 4 are each independently, hydrogen or linear or branched, substituted or unsubstituted alkyl having from 1 to 10 carbon atoms,

R 5 is independently linear or branched lower alkylene or lower alkenylene;

R 6 is independently linear or branched, substituted or unsubstituted, saturated or unsaturated lower alkyl;

the aromatic ring has from zero to four Z 1 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.

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

4. 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.

5. 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.

6. A synthetic polymer comprising monomer units represented by the formula:

wherein R is —(CR 3 R 4 ) a — or —CR 3 ═CR 4 —;

R 1 is hydrogen; saturated or unsaturated alkyl, aryl, alkylaryl or alkyl ether having from 1 to 20 carbon atoms; or —(R 5 ) q O((CR 3 R 4 ) r O) s —R 6 ;

each R 2 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; —(R 5 ) q O((CR 3 R 4 ) r O) s (R 5 ) q —; or —(R 5 ) q CO 2 ((CR 3 R 4 ) r O) s CO(R 5 ) q —;

R 3 and R 4 are each independently, hydrogen or linear or branched, substituted or unsubstituted alkyl having from 1 to 10 carbon atoms,

R 5 is independently linear or branched lower alkylene or lower alkenylene;

R 6 is independently linear or branched, substituted or unsubstituted, saturated or unsaturated lower alkyl;

the aromatic ring has from zero to four Z 1 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.

7. The polymer of claim 6 , wherein each R 1 is independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, butyl and benzyl.

8. The polymer of claim 7 , wherein R is methylene or ethylene.

9. The polymer of claim 6 , wherein each R 2 is independently selected from the group consisting of methyl, ethyl, n-propyl, —CH 2 OCH 2 —, and —(CH 2 ) q CO 2 —(CH 2 CH 2 —O) s —C(O)—(CH 2 ) q —, and —(CH 2 ) q O(CH 2 CH 2 O) s (CH 2 ) q —.

10. A pharmaceutical composition comprising the polymer of any one of claim 6 , and one or more drugs.

11. The pharmaceutical composition claim 10 , 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.

12. The composition of claim 11 , wherein said one or more drugs is an antimicrobial agent selected from the group consisting of rifampin, minocycline, gentamicin, vancomycin, triclosan, and combinations thereof.

13. The composition of claim 10 , wherein said one or more drugs is selected from the group consisting of rifampin, minocycline, anesthetics, and anti-inflammatory agents.

Assignments (4)
MERGER AND CHANGE OF NAME Recorded Feb 10, 2020
From: TYRX, INC.; MEDTRONIC, INC.
To: MEDTRONIC, INC.
Reel/Frame 051770/0976 →
MERGER Recorded May 23, 2014
From: TYRX, INC.
To: TYRX, INC.
Reel/Frame 032954/0407 →
CHANGE OF NAME Recorded Mar 19, 2013
From: TYRX PHARMA, INC.
To: TYRX, INC.
Reel/Frame 030055/0489 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 15, 2013
From: SCHWARTZ, ARTHUR; PULAPURA, SATISH; NETHULA, SARITA; RAJARAM, ARCHANA; MOSES, ARIKHA
To: TYRX PHARMA, INC.
Reel/Frame 029835/0964 →