US 5,648,088 A · Blends of absorbable polyoxaesters containing amines and/or amide groups

Abstract

The present invention describes aliphatic polyoxaesters containing amines and/or amido groups and blends thereof with other polymers that may be used to produce surgical devices such as sutures, sutures with attached needles, molded devices, and the like. The aliphatic polyoxaesters of the present invention have a first divalent repeating unit of formula I: [O--C(O)--C(R.sub.1)(R.sub.2)--O--(R.sub.3)--O--C(R.sub.1)(R.sub.2)--C(O)-- ]I and a second repeating unit of the formula: [--O--R.sub.12 --].sub.u, XVI and optionally a third repeating unit with a formula selected from the group consisting of: [--O--R.sub.4 --].sub.A, II [--O--R.sub.5 --C(O)--].sub.B, III ([--O--R.sub.5 --C(O)].sub.P --O--).sub.L G XI and combinations thereof wherein R.sub.12 contains an internal amine or internal amide group.

Claims34

Dependent claims

An aliphatic polyoxaester comprising a first divalent repeating unit of formula I:

[O--C(O)--C(R.sub.1)(R.sub.2)--O--(R.sub.3)--O--C(R.sub.1)(R.sub.2)--C(O)-- ]I
and a second repeating unit selected from the group of formulas consisting of:
[--O--R.sub.12 --].sub.U, XIV
wherein R.sub.1 and R.sub.2 are independently hydrogen or an alkyl group containing 1 to 8 carbon atoms;
R.sub.3 is an alkylene unit or is an oxyalkylene group of the following formula:
--[((CH.sub.2).sub.C --O--].sub.D --(CH.sub.2).sub.E -- IV
wherein C is an integer in the range of from 2 to about 5, D is an integer in the range of from about 0 to about 2,000, and E is an integer in the range of from about 2 to about 5, except when D is zero in which case E will be an integer from 2 to 12;
R.sub.12 is an alkylene unit containing from 2 to 8 carbon atoms and containing an internal amine (--N(R.sub.10)--) or amide (--N(R.sub.11)--);
R.sub.10 and R.sub.11 are independently hydrogen or an alloil group containing 1 to 8 carbon atoms;
and U is an integer in the range of from 1 to about 2,000.

7 more elements

A device made from an aliphatic polyoxaester comprising a first divalent repeating unit of formula I:

[O--C(O)--C(R.sub.1)(R.sub.2)--O--(R.sub.3)--O--C(R.sub.1)(R.sub.2)--C(O)-- ]I
and a second repeating unit selected from the group of formulas consisting of:
[--O--R.sub.12 --].sub.U, XIV
wherein R.sub.1 and R.sub.2 are independently hydrogen or an alkyl group containing 1 to 8 carbon atoms;
R.sub.3 is an alkylene unit or is an oxyalkylene group of the following formula:
--[(CH.sub.2).sub.C --O--].sub.D --(CH.sub.2).sub.E -- IV
wherein C is an integer in the range of from 2 to about 5, D is an integer in the range of from about 0 to about 2,000, and E is an integer in the range of from about 2 to about 5, except when D is zero in which case E will be an integer from 2 to 12;
R.sub.12 is an alkylene unit containing from 2 to 8 carbon atoms and containing an internal amine (--N(R.sub.10)--) or amide (--N(R.sub.11);
R.sub.10 and R.sub.11 are independently hydrogen or an alkyl group containing 1 to 8 carbon atoms;
and U is an integer in the rage of from 1 to about 2,000.

7 more elements

A device coated with an absorbable coating comprising an aliphatic polyoxaester having a first divalent repeating unit of formula I:

[O--C(O)--C(R.sub.1)(R.sub.2)--O--(R.sub.3)--O--C(R.sub.1)(R.sub.2)--C(O)-- ]I
and a second repeating unit of formula:
[--O--R.sub.12 --].sub.U, XIV
and combinations thereof, wherein R.sub.1 and R.sub.2 are independently hydrogen or an alkyl group containing 1 to 8 carbon atoms;
R.sub.3 is an alkylene unit or is an oxyalkylene group of the following formula:
--[(CH.sub.2).sub.C --O--].sub.D --(CH.sub.2).sub.E -- IV
wherein C is an integer in the range of from 2 to about 5, D is an integer in the range of from about 0 to about 2,000, and E is an integer in the range of from about 2 to about 5, except when D is zero in which case E will be an integer from 2 to 12;
R.sub.12 is an alkylene unit containing from 2 to 8 carbon atoms and containing an internal amine (--N(R.sub.10)--) or amide (--N(R.sub.11)--);
R.sub.10 and R.sub.11 are independently hydrogen or an alkyl group containing 1 to 8 carbon atoms;
and U is an integer in the range of from 1 to about 2,000;
wherein the inherent viscosity of the polyoxaester is in the range of from about 0.05 to about 2.0 deciliters per gram (dl/g) as measured in a 0.1 g/dl solution of hexafluoroisopropanol (HFIP) at 25.degree. C.

8 more elements

A drug delivery matrix comprising a drug and an aliphatic polyoxaester having a first divalent repeating unit of formula I:

[O--C(O)--C(R.sub.1)(R.sub.2)--O--(R.sub.3)--O--C(R.sub.1)(R.sub.2)--C(O)-- ]I
and a second repeating unit of formula:
[--O--R.sub.12 --].sub.U, XIV
wherein R.sub.1 and R.sub.2 are independently hydrogen or an alkyl group containing 1 to 8 carbon atoms;
R.sub.3 is an alkylene unit or is an oxyalkylene group of the following formula:
--[(CH.sub.2).sub.C --O--].sub.D --(CH.sub.2).sub.B -- IV
wherein C is an integer in the range of from 2 to about 5, D is an integer in the range of from about 0 to about 2,000, and E is an integer in the range of from about 2 to about 5, except when D is zero in which case E will be an integer from 2 to 12;
R.sub.12 is an alkylene unit containing from 2 to 8 carbon atoms and containing an internal amine (--N(R.sub.10)--) or amide (--N(R.sub.11)--);
R.sub.10 and R.sub.11 are independently hydrogen or an alkyl group containing 1 to 8 carbon atoms;
and U is an integer in the range of from 1 to about 2,000.

7 more elements

An aliphatic polyoxaester comprising a first divalent repeating unit of formula I:

[O--C(O)--C(R.sub.1)(R.sub.2 --O--(R.sub.3)--O--C(R.sub.1)(R.sub.2)--C(O)--]I
and two second repeating unit of the formulas:
[--O--R.sub.5 --C(O)--].sub.B, and III
([--O--R.sub.13 --C(O)].sub.P --O--).sub.L G XI
wherein R.sub.1 and R.sub.2 are independently hydrogen or an alkyl group containing 1 to 8 carbon atoms;
R.sub.3 is an alkylene unit or is an oxyalkylene group of the following formula:
--[(CH.sub.2).sub.C --O--].sub.D --(CH.sub.2).sub.E -- IV
wherein C is an integer in the range of from 2 to about 5, D is an integer in the range of from about 0 to about 2,000, and E is an integer in the range of from about 2 to about 5, except when D is zero, in which case E will be from 2 to 12;
R.sub.5 and R.sub.13 are different and are selected from the group consisting of --C(R.sub.6)(R.sub.7)--, --(CH.sub.2).sub.3 --O--, --CH.sub.2 --CH.sub.2 --O--CH.sub.2 --, --CR.sub.8 H--CH.sub.2 --, --(CH.sub.2).sub.5 --, --(CH.sub.2).sub.F --O--C(O)-- and --(CH.sub.2).sub.K --C(O)--CH.sub.2 --;
R.sub.6 and R.sub.7 are independently hydrogen or an alkyl containing from 1 to 8 carbon atoms;
R.sub.8 is hydrogen or methyl;
F and K are integers in the range of from 2 to 6;
B is an integer in the range of from 1 to n such that the number average molecular weight of formula III is less than about 200,000;
P is an integer in the range of from 1 to m such that the number average molecular weight of formula XI is less than about 1,000,000;
G represents the residue minus from 1 to L hydrogen atoms from the hydroxyl groups of an alcohol previously containing from 1 to about 200 hydroxyl groups;
and L is an integer from about 1 to about 200.

13 more elements

A device made from an aliphatic polyoxaester comprising a first divalent repeating unit of formula I:

[O--C(O)--C(R.sub.1)(R.sub.2 (O)(R.sub.3)--O--C(R.sub.1)(R.sub.2)--C(O)--]I
and two second repeating unit selected from the group of formulas consisting of:
[--O--R.sub.3 --C(O)--].sub.B, III
([--O--R.sub.13 --C(O)].sub.P --O--).sub.L G XI
wherein R.sub.1 and R.sub.2 are independently hydrogen or an alkyl group containing 1 to 8 carbon atoms;
R.sub.3 is an alkylene unit or is an oxyalkylene group of the following formula:
--[(CH.sub.2).sub.C --O--].sub.D --(CH.sub.2).sub.E -- IV
wherein C is an integer in the range of from 2 to about 5, D is an integer in the range of from about 0 to about 2,000, and E is an integer in the range of from about 2 to about 5, except when D is zero, in which case E will be from 2 to 12;
R.sub.5 and R.sub.13 are different and are selected from the group consisting of --C(R.sub.6)(R.sub.7)--, --(CH.sub.2).sub.3 --O--, --CH.sub.2 --CH.sub.2 --O--CH.sub.2 --, --CR.sub.8 H--CH.sub.2 --, --(CH.sub.2).sub.5 --, (CH.sub.2).sub.8 --O--C(O)-- and --(CH.sub.2).sub.K --C(O)--CH.sub.2 --;
R.sub.6 and R.sub.7 are independently hydrogen or an alkyl containing from 1 to 8 carbon atoms;
R.sub.8 is hydrogen or methyl;
F and K are integers in the range of from 2 to 6;
B is an integer in the range of from 1 to n such that the number average molecular weight of formula III is less than about 200,000;
P is an integer in the range of from 1 to m such that the number average molecular weight of formula XI is less than about 1,000,000;
G represents the residue minus from 1 to L hydrogen atoms from the hydroxyl groups of an alcohol previously containing from 1 to about 200 hydroxyl groups;
and L is an integer from about 1 to about 200.

13 more elements

A device coated with an absorbable coating comprising an aliphatic polyoxaester having a first divalent repeating unit of formula I:

[O--C(O)--C(R.sub.1)(R.sub.2)--O--(R.sub.3)--O--C(R.sub.1)(R.sub.2)--C(O)-- ]I
and two second repeating unit of the formulas:
[--O--R.sub.5 --C(O)--].sub.B, III
([--O--R.sub.13 --C(O)].sub.P --O--).sub.L G XI
wherein R.sub.1 and R.sub.2 are independently hydrogen or an alkyl group containing 1 to 8 carbon atoms;
R.sub.3 is an alkylene unit or is an oxyalkylene group of the following formula:
--[(CH.sub.2).sub.C --O--].sub.D --(CH.sub.E -- IV
wherein C is an integer in the range of from 2 to about 5, D is an integer in the range of from about 0 to about :2,000, and E is an integer in the range of from about 2 to about 5, except when D is zero, in which case E will be from 2 to 12;
R.sub.5 and R.sub.13 are different and are selected from the group consisting of --C(R.sub.6)(R.sub.7)--, --(CH.sub.2).sub.3 --O--, --CH.sub.2 --CH.sub.2 --O--CH.sub.2 --, --CR.sub.8 H--CH.sub.2 --, --(CH.sub.2).sub.5 --, --(CH.sub.2).sub.F --O--C(O)-- and --(CH.sub.2).sub.K --C(O)--CH.sub.2 --;
R.sub.6 and R.sub.7 are independently hydrogen or an alkyl containing from 1 to 8 carbon atoms;
R.sub.8 is hydrogen or methyl;
F and K are integers in the range of from 2 to 6;
B is an integer in the range of from 1 to n such that the number average molecular weight of formula III is less than about 200,000;
P is an integer in the range of from 1 to m such that the number average molecular weight of formula XI is less than about 1,000,000;
G represents the residue minus from 1 to L hydrogen atoms from the hydroxyl groups of an alcohol previously containing from 1 to about 200 hydroxyl groups;
and L is an integer from about 1 to about 200 wherein the inherent viscosity of the polyoxaester is in the range of from about 0.05 to about deciliters per gram (dl/g) as measured in a 0.1 g/dl solution of hexafluoroisopropanol (HFIP) at 25.degree. C.

13 more elements

A drug delivery matrix comprising a drug and an aliphatic polyoxaester having a first divalent repeating unit of formula I:

[O--C(O)--C(R.sub.1)(R.sub.2)--O--(R.sub.3)--O--C(R.sub.1)(R.sub.2)--C(O)-- ]I
and two second repeating unit of the formulas:
[--O--R.sub.5 --C(O)--].sub.B, III
([--O--R.sub.13 C(O)].sub.P --O--).sub.L G XI
wherein R.sub.1 and R.sub.2 are independently hydrogen or an alkyl group containing 1 to 8 carbon atoms;
R.sub.3 is an alkylene unit or is an oxyalkylene group of the following formula:
--[(CH.sub.2).sub.C --O--].sub.D --(CH.sub.2).sub.E -- IV
wherein C is an integer in the range of from 2 to about 5, D is an integer in the range of from about 0 to about 2,000, and E is an integer in the range of from about 2 to about 5, except when D is zero, in which case E will be from 2 to 12;
R.sub.5 and R.sub.13 are different and are selected from the group consisting of --C(R.sub.6)(R.sub.7)--, --(CH.sub.2).sub.3 --O--, --CH.sub.2 --CH.sub.2 --O--CH.sub.2 --, --CR.sub.8 H--CH.sub.2 --, --(CH.sub.2).sub.5 --, --(CH.sub.2).sub.F --O--C(O)-- and --(CH.sub.2).sub.K --C(O)--CH.sub.2 --;
R.sub.6 and R.sub.7 are independently hydrogen or an alkyl containing from 1 to 8 carbon atoms;
R.sub.8 is hydrogen or methyl;
F and K are integers in the range of from 2 to 6;
B is an integer in the range of from 1 to n such that the number average molecular weight of formula III is less than about 200,000;
P is an integer in the range of from 1 to m such that the number average molecular weight of formula XI is less than about 1,000,000;
G represents the residue minus from 1 to L hydrogen atoms from the hydroxyl groups of an alcohol previously containing from 1 to about 200 hydroxyl groups;
and L is an integer from about 1 to about 200 wherein the inherent viscosity of the polyoxaester is in the range of from about 0.05 to about 20 deciliters per gram (dl/g) as measured in a. 0.1 g/dl solution of hexafluoroisopropanol (HFIP) at 25.degree. C.

13 more elements

Dependencies are inferred from the claim text.

Blends of absorbable polyoxaesters containing amines and/or amide groups

Life of this patent

Blends of absorbable polyoxaesters containing amines and/or amide groups

Life of this patent

Abstract

Claims34