US 5,597,579 AGranted

Blends of absorbable polyoxaamides

AssigneeEthicon, Inc.

InventorsRao S. Bezwada, Dennis D. Jamiolkowski

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Abstract

The present invention describes an aliphatic polyoxaamide polymer and blends thereof that may be used to produce surgical devices such as sutures, sutures with attached needles, molded devices, and the like. The aliphatic polyoxaamide of the present invention have a first divalent repeating unit of formula I: [X--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: [--Y--R.sub.17 --].sub.T, I [--O--R.sub.5 --C(O)--].sub.B, and II ([--O--R.sub.9 --C(O)].sub.P --O--).sub.L G XI and combinations thereof, wherein X and Y are selected from the group consisting of --O-- and --N(R)--, provided both X and Y are not both --O-- and may be blended with a second polymer that is preferably biocompatable.

Claims26

Dependent claims

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

[X--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:
[--Y--R.sub.17 --].sub.T, II
[--O--R.sub.5 --C(O)--].sub.B, III
([--O--R.sub.9 --C(O)].sub.P --O--).sub.L G XI
and combinations thereof, wherein X and Y are selected from the group consisting of --O-- and --N(R)--, provided that X and Y cannot both be --O--;
R, R.sub.1 and R.sub.2 are independently selected from the group consisting of hydrogen and an alkyl group containing 1 to 8 carbon atoms;
R.sub.3 is selected from the group consisting of an alkylene unit and 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 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 in the range of from 2 to 12;
R.sub.17 is an alkylene unit containing from 2 to 8 carbon atoms which may have substituted therein an internal ether oxygen, an internal --N(R.sub.18)-- or an internal --C(O)--N(R.sub.21)--;
T is an integer in the range of from 1 to 2,000;
R.sub.18 and R.sub.21 are independently selected from the group consisting of hydrogen and an alkyl group containing 1 to 8 carbon atoms;
R.sub.5 and R.sub.9 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 selected from the group consisting of hydrogen and an alkyl containing from 1 to 8 carbon atoms;
R.sub.8 is selected from the group consisting of hydrogen and methyl;
F and K are independently selected integer 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.

18 more elements

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

[X--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:
[--Y--R.sub.17 --].sub.T, II
[--O--R.sub.5 C(O)--].sub.B, III
([--O--R.sub.9 --C(O)].sub.P --O--).sub.L G XI
and combinations thereof, wherein X and Y are selected from the group consisting of --O-- and --N(R)--, provided that X and Y cannot both be --O--;
R, R.sub.1 and R.sub.2 are independently selected from the group consisting of hydrogen and an alkyl group containing 1 to 8 carbon atoms;
R.sub.3 is selected from the group consisting of an alkylene unit and 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 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 in the range of from 2 to 12;
R.sub.17 is an alkylene unit containing from 2 to 8 carbon atoms which may have substituted therein an internal ether oxygen, an internal --N(R.sub.18)-- or an internal --C(O)--N(R.sub.21)--;
T is an integer in the range of from 1 to 2,000;
R.sub.18 and R.sub.21 are independently selected from the group consisting of hydrogen and an alkyl group containing 1 to 8 carbon atoms;
R.sub.5 and R.sub.9 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 selected from the group consisting of hydrogen and an alkyl containing from 1 to 8 carbon atoms;
R.sub.8 is selected from the group consisting of hydrogen and methyl;
F and K are independently selected integer 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.

18 more elements

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

[X--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:
[--Y--R.sub.17 --].sub.T, II
[--O--R.sub.5 --C(O)--].sub.B, III
([--O--R.sub.9 --C(O)].sub.P --O--).sub.L G XI
and combinations thereof, wherein X and Y are selected from the group consisting of --O-- and --N(R)--, provided that X and Y cannot both be --O--;
R, R.sub.1 and R.sub.2 are independently selected from the group consisting of hydrogen and an alkyl group containing 1 to 8 carbon atoms;
R.sub.3 is selected from the group consisting of an alkylene unit and 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 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 in the range of from 2 to 12;
R.sub.17 is an alkylene unit containing from 2 to 8 carbon atoms which may have substituted therein an internal ether oxygen, an internal --N(R.sub.18)-- or an internal --C(O)--N(R.sub.21)--;
T is an integer in the range of from 1 to 2,000;
R.sub.18 and R.sub.21 are independently selected from the group consisting of hydrogen and an alkyl group containing 1 to 8 carbon atoms;
R.sub.5 and R.sub.9 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 selected from the group consisting of hydrogen and an alkyl containing from 1 to 8 carbon atoms;
R.sub.8 is selected from the group consisting of hydrogen and methyl;
F and K are independently selected integer 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 polyoxaamide 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.

19 more elements

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

[X--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:
[--Y--R.sub.17 --].sub.T, II
[--O--R.sub.5 --C(O)--].sub.B, III
([--O--R--C(O)].sub.P --O--).sub.L G XI
and combinations thereof, wherein X and Y are selected from the group consisting of --O-- and --N(R)--, provided that X and Y cannot both be --O--;
R, R.sub.1 and R.sub.2 are independently selected from the group consisting of hydrogen and an alkyl group containing 1 to 8 carbon atoms;
R.sub.3 is selected from the group consisting of an alkylene unit and 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 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 in the range of from 2 to 12;
R.sub.17 is an alkylene unit containing from 2 to 8 carbon atoms which may have substituted therein an internal ether oxygen, an internal --N(R.sub.18)-- or an internal --C(O)--N(R.sub.21)--;
T is an integer in the range of from 1 to 2,000;
R.sub.18 and R.sub.21 are independently selected from the group consisting of hydrogen and an alkyl group containing 1 to 8 carbon atoms;
R.sub.5 and R.sub.9 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 selected from the group consisting of hydrogen and an alkyl containing from 1 to 8 carbon atoms;
R.sub.8 is selected from the group consisting of hydrogen and methyl;
F and K are independently selected integer 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 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.

18 more elements

Dependencies are inferred from the claim text.

Facts

Application: 08/611,532Filed 5 Mar 1996 · continuation in part
Priority: 6 Mar 1995
Granted: 28 Jan 1997
Term ends: Not estimatedThe source records don’t support an estimate.

Classification37 codes

C08G 69/44
Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule: polyester-amides
A61K 9/204
Obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, polyethylene oxide, poloxamers:…
A61L 15/225
Containing macromolecular materials: mixtures of macromolecular compounds
A61L 15/26
Containing macromolecular materials: macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated…