US 5,595,751 A · Absorbable polyoxaesters containing amines and/or amido groups

Abstract

The present invention describes a new aliphatic polyoxaesters that is bioabsorbable and may be used to produce surgical devices such as sutures, sutures with attached needles, molded devices, and the like. The invention also contemplates a process for producing these polyesters. 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.

Claims33

Dependent claims

An aliphatic polyoxaesters 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 12, 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 1,000.

7 more elements

A device made from an aliphatic polyoxaesters 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)--.sub.] 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 12, 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 1,000.

7 more elements

A device coated with an absorbable coating comprising an aliphatic polyoxaesters 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 12, 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 1,000;
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.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 12, 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 1,000.

7 more elements

An aliphatic polyoxaesters 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 12, 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(O)(R.sub.6)(R.sub.7)--, --(CH.sub.2)3--O--, --CH.sub.2 --CH.sub.2 --O--CH.sub.2 --, --CR.sub.8 H--CH.sub.2 --, --(CH.sub.2).sub.4 --, --(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;
Rs 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 40,000;
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 40,000;
G represents the residue minus from 1 to L hydrogen atoms from the hydroxyl groups of an alcohol previously containing from 2 to 12 hydroxyl groups;
and L is an integer from about 1 to about 12.

13 more elements

A device coated with an absorbable coating comprising an aliphatic polyoxaesters 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--) XI
wherein R.sub.l 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 12, 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(O)(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.4 --, --(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 40,000;
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 40,000;
G represents the residue minus from 1 to L hydrogen atoms from the hydroxyl groups of an alcohol previously containing from 2 to 12 hydroxyl groups;
and L is an integer from about 1 to about 12 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.

13 more elements

A drug delivery matrix comprising a drug and an aliphatic polyoxaesters 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 12, 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.4 --, --(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 40,000;
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 40,000;
G represents the residue minus from 1 to L hydrogen atoms from the hydroxyl groups of an alcohol previously containing from 2 to 12 hydroxyl groups;
and L is an integer from about 1 to about 12 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.

13 more elements

Dependencies are inferred from the claim text.

Absorbable polyoxaesters containing amines and/or amido groups

Life of this patent

Absorbable polyoxaesters containing amines and/or amido groups

Life of this patent

Abstract

Claims33