Bioabsorbable polyesteramides and uses thereof

Abstract

Novel biodegradable polyesteramides derived from optionally functionalized diacids and optionally functionalized diamines or from compounds having both optionally functionalized acid and optionally functionalized amine moieties, their preparation, and absorbable surgical articles fabricated therefrom, such as monofilament and multifilament sutures, films, sheets, plates, clips, staples, pins, screws, stents, stent coatings, packaging materials, and other implantable surgical devices, and the like, are described herein.

1 . (canceled) 
     
     
         2 . A polyesteramide comprising Formula IV:
   —[—(X—O—) a —C(═O)—R 1 —C(═O)—(O—Y) b —NH—R 2 —NH—] n —  IV
   
       wherein:
 each R 1  and R 2  is independently alkylene, cycloalkylenealkylene, arylenealkylene, arylenealkylenearylene, cycloalkylenealkylenecycloalkylene, or arylenealkylenecycloalkylene, wherein:
 (1) one or more of the —CH 2 — moieties in the alkylene chain portion of an alkylene, cycloalkylenealkylene, arylenealkylene, arylenealkylenearylene, cycloalkylenealkylenecycloalkylene, or arylenealkylenecycloalkylene moiety are optionally replaced by —O— or —S—; or 
 (2) one or more of the —CH 2 —CH 2 — moieties in the alkylene chain portion of an alkylene, cycloalkylenealkylene, arylenealkylene, arylenealkylenearylene, cycloalkylenealkylenecycloalkylene, or arylenealkylenecycloalkylene moiety are optionally replaced by —C(═O)—O— or —O—C(═O)—; 
 
 each X is independently —C(═O)—CH(CH 3 )—, —C(═O)—(CH 2 ) y —, or —C(═O)—(CH 2 CH 2 O) Z —CH 2 —; 
 each Y is independently —CH(CH 3 )—C(═O)—, —(CH 2 ) y —C(═O)—, or —(CH 2 CH 2 O) z —CH 2 —C(═O)—; 
 each a and b is independently an integer from about 2 to about 6; 
 each y and z is independently an integer from about 1 to about 24; and 
 n is an integer from about 5 to about 5000. 
 
     
     
         3 . A polyesteramide comprising Formula VI:
   —[C(═O)—R 1 —C(═O)—(O—Y 1 ) b —NH—R 2 —NH—(X 1 —I—) a —] n —;  VI
   
       wherein:
 each R 1  and R 2  is independently alkylene, cycloalkylenealkylene, arylenealkylene, arylenealkylenearylene, cycloalkylenealkylenecycloalkylene, or arylenealkylenecycloalkylene, wherein:
 (1) one or more of the —CH 2 — moieties in the alkylene chain portion of an alkylene, cycloalkylenealkylene, arylenealkylene, arylenealkylenearylene, cycloalkylenealkylenecycloalkylene, or arylenealkylenecycloalkylene moiety are optionally replaced by —O— or —S—; or 
 (2) one or more of the —CH 2 —CH 2 — moieties in the alkylene chain portion of an alkylene, cycloalkylenealkylene, arylenealkylene, arylenealkylenearylene, cycloalkylenealkylenecycloalkylene, or arylenealkylenecycloalkylene moiety are optionally replaced by —C(═O)—O— or —O—C(═O)—; 
 
 each X 1  is independently —C(═O)—CH(CH 3 )—, —C(═O)—(CH 2 ) y —, or —C(═O)—(CH 2 CH 2 O) z —CH 2 —; 
 each Y 1  is independently —CH(CH 3 )—C(═O)—, —(CH 2 ) y —C(═O)—, or —(CH 2 CH 2 O) z —CH 2 —CH 2 —C(═O)—; 
 each a and b is independently an integer from about 1 to about 6; 
 each y and z is independently an integer from about 1 to about 24; and 
 n is an integer from about 5 to about 5000. 
 
     
     
         4 . A polyesteramide comprising Formula VIII:
   —[(X—O—) a —C(═O)—R 5 —NH—(X 1 —O—) a —] n —  VIII
   
       wherein:
 each R 5  is independently alkylene, cycloalkylenealkylene, arylenealkylene, arylenealkylenearylene, cycloalkylenealkylenecycloalkylene, or arylenealkylenecycloalkylene, wherein:
 (1) one or more of the —CH 2 — moieties in the alkylene chain portion of an alkylene, cycloalkylenealkylene, arylenealkylene, arylenealkylenearylene, cycloalkylenealkylenecycloalkylene, or arylenealkylenecycloalkylene moiety are optionally replaced by —O— or —S—; or 
 (2) one or more of the —CH 2 —CH 2 — moieties in the alkylene chain portion of an alkylene, cycloalkylenealkylene, arylenealkylene, arylenealkylenearylene, cycloalkylenealkylenecycloalkylene, or arylenealkylenecycloalkylene moiety are optionally replaced by —C(═O)—O— or —O—C(═O)—; 
 
 each X and X 1  is independently —C(═O)—CH(CH 3 )—, —C(═O)—(CH 2 ) y —, or —C(═O)—(CH 2 CH 2 O) z —CH 2 —; 
 each a is independently an integer from about 1 to about 6; 
 each y and z is independently an integer from about 1 to about 24; and 
 n is an integer from about 5 to about 5000. 
 
     
     
         5 . (canceled) 
     
     
         6 . A polyesteramide comprising:
 a polymer wherein:   one or more of the amido linkages in the polymer backbone are replaced with —[C(═O)—(O—X 1 ) a —N]— linkages; or   one or more of the ester linkages in the polymer backbone are replaced with —[C(═O)—(O—X 2 ) b —O]— linkages;   wherein:
 each X 1  and each X 2  is independently selected from: —CH(CH 3 )—C(═O)—, —(CH 2 ) y —C(═O)—and —(CH 2 CH 2 O) z —CH 2 —C(═O)—; and 
   each a and each b is independently an integer from 1 to about 24, provided that at least one a or at least one b is an integer from 2 to about 24.   
     
     
         7 . A polyesteramide according to  claim 6 , wherein:
 one or more of the amido linkages in the polymer backbone are replaced with —[C(═O)—(O—X 1 ) a —N]— linkages;   and one or more of the ester linkages in the polymer backbone are replaced with —[C(═O)—(O—X 2 ) b —O]— linkages.   
     
     
         8 . A polyesteramide according to  claim 6 , wherein each a and each b is independently an integer from 1 to about 12. 
     
     
         9 . A polyesteramide according to  claim 8 , wherein each a and each b is independently an integer from 1 to about 6. 
     
     
         10 . A polyesteramide according to  claim 9 , wherein each a and each b is independently an integer from 1 to about 3. 
     
     
         11 . A surgical article comprising the polyesteramide of  claim 2 . 
     
     
         12 . A surgical article of  claim 11 , wherein the polyesteramide is further polymerized with a lactone monomer. 
     
     
         13 . A surgical article of  claim 12 , wherein the lactone monomer is selected from the group consisting of glycolide, lactide, ε-caprolactone, trimethylene carbonate, and p-dioxanone. 
     
     
         14 . A surgical article of  claim 11 , wherein the article is a stent. 
     
     
         15 . A surgical article of  claim 11 , wherein the article is a scaffold for tissue engineering comprising a porous structure for the attachment and proliferation of cells. 
     
     
         16 . A coating for a stent, comprising the polyesteramide of  claim 11 . 
     
     
         17 . A drug delivery system, comprising the polyesteramide of  claim 11  physically in admixture with a biologically or pharmacologically active agent. 
     
     
         18 . A drug delivery system of  claim 17 , wherein the biologically or pharmacologically active agent is physically embedded or dispersed into the polymer and the polymer is in the form of a polymeric matrix. 
     
     
         19 . A surgical article of  claim 11 , wherein the article is a surgical suture. 
     
     
         20 . A surgical article of  claim 11 , wherein the article is an adhesion prevention barrier film. 
     
     
         21 . A surgical article of  claim 11 , wherein the article is a film, sheet, plate, clip, staple, pin, screw, or mesh. 
     
     
         22 . A biodegradable packaging material comprising the polyesteramide of  claim 2 . 
     
     
         23 . A biodegradable packaging material of  claim 22 , wherein the polyesteramide has been further polymerized with a lactone monomer selected from glycolide, lactide, ε-caprolactone, trimethylene carbonate, and p-dioxanone. 
     
     
         24 . (canceled)