Bioabsorbable and biocompatible polyurethanes and polyamides for medical devices

An absorbable polyamide polymer polymerized from at least one monomer compound of the formula:

• Wherein each X represents a member independently selected from the group consisting of:
• —CH2COO— (glycolic acid moiety);
• —CH(CH3)COO— (lactic acid moiety);
• —CH2CH2OCH2COO— (dioxanone moiety);
• —CH2CH2CH2CH2CH2COO— (caprolactone moiety);
• —(CH2)yCOO— where y is one of the numbers 2,3,4 and 6-24 inclusive;
• and
• —(CH2CH2Oz′CH2COO— where z′ is an integer between 2 and 24, inclusive;
• each Y represents a member independently selected from the group consisting of:
• —COCH2O— (glycolic ester moiety);
• —COCH(CH3)O— (lactic ester moiety);
• —COCH2OCH2CH2O— (dioxanone ester moiety);
• —COCH2CH2CH2CH2CH2O— (caprolactone ester moiety);
• —CO(CH2)mO— where m is an integer between 2-4 and 6-24 inclusive;
• and
• —COCH2O(CH2CH2O)n— where n is an integer between 2 and 24, inclusive;
• each R′ is independently a hydrogen, benzyl or an alkyl group, the alkyl group being either straight-chained or branched;
• each p is independently an integer between 1 and 4, inclusive;
• Z is O or NH;
• and
• Rn represents one or more members selected from the group consisting of H, alkoxy, benzyloxy, aldehyde, halogen, carboxylic acid and —NO2, which is attached directly to an aromatic ring or attached through an aliphatic chain.

An absorbable polyurethane prepared from at least one monomer compound of the formula:

• Wherein each X represents a member independently selected from the group consisting of:
• —CH2COO— (glycolic acid moiety);
• —CH(CH3)COO— (lactic acid moiety);
• —CH2CH2OCH2COO— (dioxanone moiety);
• —CH2CH2CH2CH2CH2COO— (caprolactone moiety);
• —(CH2)yCOO— where y is one of the numbers 2,3,4 and 6-24 inclusive;
• and
• —(CH2CH2O)z′CH2COO— where z′ is an integer between 2 and 24, inclusive;
• each Y represents a member independently selected from the group consisting of:
• —COCH2O— (glycolic ester moiety);
• —COCH(CH3)O— (lactic ester moiety);
• —COCH2OCH2 CH2O— (dioxanone ester moiety);
• —COCH2CH2CH2CH2CH2O— (caprolactone ester moiety);
• —CO(CH2)mO— where m is an integer between 2-4 and 6-24 inclusive;
• and
• —CO CH2O(CH2CH2O)n— where n is an integer between 2 and 24, inclusive;
• each R′ is hydrogen, benzyl or an alkyl group, the alkyl group being either straight-chained or branched;
• each p is independently an integer between 1 and 4, inclusive;
• Z is O or NH;
• and
• Rn represents one or more members selected from the group consisting of H, alkoxy, benzyloxy, aldehyde, halogen, carboxylic acid and —NO2, which is attached directly to an aromatic ring or attached through an aliphatic chain.

A tissue adhesive composition comprising at least one isocyanate compound of the formula:

• Wherein each X represents a member independently selected from the group consisting of:
• —CH2COO— (glycolic acid moiety);
• —CH(CH3)COO— (lactic acid moiety);
• —CH2CH2OCH2COO— (dioxanone moiety);
• —CH2CH2CH2CH2CH2COO— (caprolactone moiety);
• —(CH2)yCOO— where y is one of the numbers 2,3,4 and 6-24 inclusive;
• and
• —(CH2CH2O)z′CH2COO— where z′ is an integer between 2 and 24, inclusive;
• each Y represents a member independently selected from the group consisting of:
• —COCH2O— (glycolic ester moiety);
• —COCH(CH3)O— (lactic ester moiety);
• —COCH2OCH2CH2O— (dioxanone ester moiety);
• —COCH2CH2CH2CH2CH2O— (caprolactone ester moiety);
• —CO(CH2)mO— where m is an integer between 2-4 and 6-24 inclusive;
• and
• —COCH2O(CH2CH2O)n— where n is an integer between 2 and 24, inclusive;
• each R′ is hydrogen, benzyl or an alkyl group, the alkyl group being either straight-chained or branched;
• each p is independently an integer between 1 and 4, inclusive;
• Z is O or NH;
• and
• Rn represents one or more members selected from the group consisting of H, alkoxy, benzyloxy, aldehyde, halogen, isocyanate, carboxylic acid and —NO2, which is attached directly to an aromatic ring or attached through an aliphatic chain.

A compound selected from the group consisting of:

• Wherein each X represents a member independently selected from the group consisting of:
• —CH2COO— (glycolic acid moiety),
• —CH(CH3)COO— (lactic acid moiety),
• —CH2CH2OCH2COO— (dioxanone moiety),
• —CH2CH2CH2CH2CH2COO— (caprolactone moiety),
• —(CH2)yCOO— where y is one of the numbers 2,3,4 or 6-24 inclusive, and
• —(CH2CH2O)z′CH2COO— where z′ is an integer between 2 and 24, inclusive;
• each Y represents a member independently selected from the group consisting of:
• —COCH2O— (glycolic ester moiety),
• —COCH(CH3)O— (lactic ester moiety),
• —COCH2OCH2CH2O— (dioxanone ester moiety),
• —COCH2CH2CH2CH2CH2O— (caprolactone ester moiety),
• —CO(CH2)mO— where m is an integer between 2-4 and 6-24 inclusive,
• —COCH2O(CH2CH2O)n— where n is an integer between 2 and 24, inclusive;
• R′ is hydrogen, benzyl or an alkyl group, the alkyl group being either straight-chained or branched;
• p is an integer between 1 and 4, inclusive;
• and
• Rn represents one or more members selected from the group consisting of H, alkoxy, benzyloxy, aldehyde, halogen, carboxylic acid and —NO2, which is attached directly to an aromatic ring or attached through an aliphatic chain.

A compound selected from the group consisting of:

• Wherein each X represents a member independently selected from the group consisting of:
• —CH2COO— (glycolic acid moiety);
• —CH(CH3)COO— (lactic acid moiety);
• —CH2CH2OCH2COO— (dioxanone moiety);
• —CH2CH2CH2CH2CH2COO— (caprolactone moiety);
• —(CH2)yCOO— where y is one of the numbers 2,3,4 and 6-24 inclusive;
• and
• —(CH2CH2O)z′CH2COO— where z′ is an integer between 2 and 24, inclusive;
• each Y represents a member independently selected from the group consisting of:
• —COCH2O— (glycolic ester moiety);
• —COCH(CH3)O— (lactic ester moiety);
• —COCH2OCH2CH2O— (dioxanone ester moiety);
• —COCH2CH2CH2CH2CH2O— (caprolactone ester moiety);
• —CO(CH2)mO— where m is an integer between 2-4 and 6-24 inclusive;
• and
• —COCH2O(CH2CH2O)n— where n is an integer between 2 and 24, inclusive;
• each R′ is independently a hydrogen, benzyl or an alkyl group, the alkyl group being either straight-chained or branched;
• each p is independently an integer between 1 and 4, inclusive;
• Z is O or NH;
• and
• Rn represents one or more members selected from the group consisting of H, alkoxy, benzyloxy, aldehyde, halogen, carboxylic acid and —NO2, which is attached directly to an aromatic ring or attached through an aliphatic chain.

A compound selected from the group consisting of:

• Wherein each X represents a member independently selected from the group consisting of:
• —CH2COO— (glycolic acid moiety);
• —CH(CH3)COO— (lactic acid moiety);
• —CH2CH2OCH2COO— (dioxanone moiety);
• —CH2CH2CH2CH2CH2COO— (caprolactone moiety);
• —(CH2)yCOO— where y is one of the numbers 2,3,4 and 6-24 inclusive;
• and
• —(CH2CH2O)z′CH2COO— where z′ is an integer between 2 and 24, inclusive;
• each Y represents a member independently selected from the group consisting of:
• —COCH2O— (glycolic ester moiety);
• —COCH(CH3)O— (lactic ester moiety);
• —COCH2OCH2CH2O— (dioxanone ester moiety);
• —COCH2CH2CH2CH2CH2O— (caprolactone ester moiety);
• —CO(CH2)mO— where m is an integer between 2-4 and 6-24 inclusive;
• and
• —COCH2O(CH2CH2O)n— where n is an integer between 2 and 24, inclusive;
• each R′ is hydrogen, benzyl or an alkyl group, the alkyl group being either straight-chained or branched;
• each p is independently an integer between 1 and 4, inclusive;
• Z is O or NH;
• and
• Rn represents one or more members selected from the group consisting of H, alkoxy, benzyloxy, aldehyde, halogen, carboxylic acid and —NO2, which is attached directly to an aromatic ring or attached through an aliphatic chain.