Polymeric biomaterials derived from monomers comprising hydroxyacids and phenol compounds and their medical uses

A biocompatible implantable polymer, comprising tissue compatible and bioresorbable recurring units including recurring units of formula:

• wherein
• y1 is 0, 1, 2, 3, or 4;
• X1 is bromine (Br) or iodine (I);
• X2 and X3 are independently selected from O, S and NR, where R is H or lower alkyl;
• R1 is selected from the group consisting of linear or branched C1-C12 alkylene;
• A is selected from the group consisting of linear or branched C1-C24 alkylene;
• R2 is selected from the group consisting of linear or branched C1-C24 alkylene;
• n1 and n2 are independently numbers from 0 to 100, and are average values which can be fractional, where the sum of n1 and n2 is at least 1;
• p is zero or 1;
• and
• A1 is a linking group selected from:
• wherein R8 is selected from a bond, C1-C30 alkylene, C2-C30 alkenylene, C2-C30 alkynylene;
• C1-C30 heteroalkylene, C2-C30 heteroalkenylene, C2-C30 heteroalkynylene, C7-C30 heteroalkylarylene, C8-C30 heteroalkynylarylene, C8-C30 heteroalkynylarylene, C7-C30 alkylarylene, C8-C30 alkenylarylene, C8-C30 alkynylarylene, and C2-C30 heteroarylene;
• and
• R9 and R10 are each independently selected from H, C1-C30 alkyl, C1-C30 heteroalkyl, C2-C30 alkenyl, C2-C30 alkynyl, C2-C30 heteroalkenyl, and C2-C30 heteroalkynyl;
• wherein each said alkyl and alkylene can be substituted with one or more of hydroxy, alkoxy, halogen, nitro, cyano, CO2R, where R is defined above, phenyl, aryl, heteroaryl, cycloalkyl, mercapto, or alkylthio;
• wherein said biocompatible polymer is tissue compatible and bioresorbable when implanted in vivo;
• and
• further comprising a recurring unit of the formula:
• wherein B is —O—((CHR)p—O)q—;
• each R is independently H or C1 to C3 alkyl;
• p and q are each independently an integer in the range of from 1 to 100;
• and A1 is as defined above, independently from any other A1.

A biocompatible implantable polymer, consisting essentially of tissue compatible and bioresorbable recurring units including recurring units of formula:

• wherein
• y1 is 0, 1, 2, 3, or 4;
• X1 is bromine (Br) or iodine (I);
• R1 is selected from the group consisting of linear or branched C1-C12 alkylene;
• A is selected from the group consisting of linear or branched C1-C24 alkylene;
• n1 and n2 are independently numbers from 0 to 100, and are average values which can be fractional, where the sum of n1 and n2 is at least 1;
• p is zero or 1;
• and
• A1 is a linking group selected from:
• wherein R8 is selected from a bond, C1-C30 alkylene, C2-C30 alkenylene, C2-C30 alkynylene;
• C1-C30 heteroalkylene, C2-C30 heteroalkenylene, C2-C30 heteroalkynylene, C7-C30 heteroalkylarylene, C8-C30 heteroalkynylarylene, C8-C30 heteroalkynylarylene, C7-C30 alkylarylene, C8-C30 alkenylarylene, C8-C30 alkynylarylene, and C2-C30 heteroarylene;
• and
• R9 and R10 are each independently selected from H, C1-C30 alkyl, C1-C30 heteroalkyl, C2-C30 alkenyl, C2-C30 alkynyl, C2-C30 heteroalkenyl, and C2-C30 heteroalkynyl;
• wherein each said alkyl and alkylene can be substituted with one or more of hydroxy, alkoxy, halogen, nitro, cyano, phenyl, aryl, heteroaryl, cycloalkyl, mercapto, alkylthio, or CO2R, where R is H or lower alkyl;
• wherein n2 is greater than zero, R3 is methyl, and the subunit is derived from L-lactic acid, D-lactic acid, or D,L-lactic acid;
• and
• wherein said biocompatible polymer is tissue compatible and bioresorbable when implanted in vivo.