Blends of absorbable polyoxaesters containing amines and/or amide groups
First Claim
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1. An aliphatic polyoxaester comprising a first divalent repeating unit of formula I:
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space="preserve" listing-type="equation">[O--C(O)--C(R.sub.1)(R.sub.2)--O--(R.sub.3)--O--C(R.sub.1)(R.sub.2)--C(O)--]Iand a second repeating unit selected from the group of formulas consisting of;
space="preserve" listing-type="equation">[--O--R.sub.12 --].sub.U, XIVwherein R1 and R2 are independently hydrogen or an alkyl group containing 1 to 8 carbon atoms;
R3 is an alkylene unit or is an oxyalkylene group of the following formula;
space="preserve" listing-type="equation">--[((CH.sub.2).sub.C --O--].sub.D --(CH.sub.2).sub.E -- IVwherein 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;
R12 is an alkylene unit containing from 2 to 8 carbon atoms and containing an internal amine (--N(R10)--) or amide (--N(R11)--);
R10 and R11 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.
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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 R12 contains an internal amine or internal amide group.
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Citations
34 Claims
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1. An aliphatic polyoxaester comprising a first divalent repeating unit of formula I:
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space="preserve" listing-type="equation">[O--C(O)--C(R.sub.1)(R.sub.2)--O--(R.sub.3)--O--C(R.sub.1)(R.sub.2)--C(O)--]Iand a second repeating unit selected from the group of formulas consisting of;
space="preserve" listing-type="equation">[--O--R.sub.12 --].sub.U, XIVwherein R1 and R2 are independently hydrogen or an alkyl group containing 1 to 8 carbon atoms;
R3 is an alkylene unit or is an oxyalkylene group of the following formula;
space="preserve" listing-type="equation">--[((CH.sub.2).sub.C --O--].sub.D --(CH.sub.2).sub.E -- IVwherein 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;
R12 is an alkylene unit containing from 2 to 8 carbon atoms and containing an internal amine (--N(R10)--) or amide (--N(R11)--);
R10 and R11 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. - View Dependent Claims (2, 3, 4, 5, 34)
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6. A device made from an aliphatic polyoxaester comprising a first divalent repeating unit of formula I:
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space="preserve" listing-type="equation">[O--C(O)--C(R.sub.1)(R.sub.2)--O--(R.sub.3)--O--C(R.sub.1)(R.sub.2)--C(O)--]Iand a second repeating unit selected from the group of formulas consisting of;
space="preserve" listing-type="equation">[--O--R.sub.12 --].sub.U, XIVwherein R1 and R2 are independently hydrogen or an alkyl group containing 1 to 8 carbon atoms;
R3 is an alkylene unit or is an oxyalkylene group of the following formula;
space="preserve" listing-type="equation">--[(CH.sub.2).sub.C --O--].sub.D --(CH.sub.2).sub.E -- IVwherein 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;
R12 is an alkylene unit containing from 2 to 8 carbon atoms and containing an internal amine (--N(R10)--) or amide (--N(R11);
R10 and R11 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. - View Dependent Claims (7, 8, 9, 10, 11, 12, 13, 14)
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15. A device coated with an absorbable coating comprising an aliphatic polyoxaester having a first divalent repeating unit of formula I:
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space="preserve" listing-type="equation">[O--C(O)--C(R.sub.1)(R.sub.2)--O--(R.sub.3)--O--C(R.sub.1)(R.sub.2)--C(O)--]Iand a second repeating unit of formula;
space="preserve" listing-type="equation">[--O--R.sub.12 --].sub.U, XIVand combinations thereof, wherein R1 and R2 are independently hydrogen or an alkyl group containing 1 to 8 carbon atoms;
R3 is an alkylene unit or is an oxyalkylene group of the following formula;
space="preserve" listing-type="equation">--[(CH.sub.2).sub.C --O--].sub.D --(CH.sub.2).sub.E -- IVwherein 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;
R12 is an alkylene unit containing from 2 to 8 carbon atoms and containing an internal amine (--N(R10)--) or amide (--N(R11)--);
R10 and R11 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°
C. - View Dependent Claims (16, 17, 18, 19, 20, 21)
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22. A drug delivery matrix comprising a drug and an aliphatic polyoxaester having a first divalent repeating unit of formula I:
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space="preserve" listing-type="equation">[O--C(O)--C(R.sub.1)(R.sub.2)--O--(R.sub.3)--O--C(R.sub.1)(R.sub.2)--C(O)--]Iand a second repeating unit of formula;
space="preserve" listing-type="equation">[--O--R.sub.12 --].sub.U, XIVwherein R1 and R2 are independently hydrogen or an alkyl group containing 1 to 8 carbon atoms;
R3 is an alkylene unit or is an oxyalkylene group of the following formula;
space="preserve" listing-type="equation">--[(CH.sub.2).sub.C --O--].sub.D --(CH.sub.2).sub.B -- IVwherein 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;
R12 is an alkylene unit containing from 2 to 8 carbon atoms and containing an internal amine (--N(R10)--) or amide (--N(R11)--);
R10 and R11 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. - View Dependent Claims (23, 24, 25)
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26. An aliphatic polyoxaester comprising a first divalent repeating unit of formula I:
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space="preserve" listing-type="equation">[O--C(O)--C(R.sub.1)(R.sub.2 --O--(R.sub.3)--O--C(R.sub.1)(R.sub.2)--C(O)--]Iand two second repeating unit of the formulas;
space="preserve" listing-type="equation">[--O--R.sub.5 --C(O)--].sub.B, and III
space="preserve" listing-type="equation">([--O--R.sub.13 --C(O)].sub.P --O--).sub.L G XIwherein R1 and R2 are independently hydrogen or an alkyl group containing 1 to 8 carbon atoms;
R3 is an alkylene unit or is an oxyalkylene group of the following formula;
space="preserve" listing-type="equation">--[(CH.sub.2).sub.C --O--].sub.D --(CH.sub.2).sub.E -- IVwherein 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;
R5 and R13 are different and are selected from the group consisting of --C(R6)(R7)--, --(CH2)3 --O--, --CH2 --CH2 --O--CH2 --, --CR8 H--CH2 --, --(CH2)5 --, --(CH2)F --O--C(O)-- and --(CH2)K --C(O)--CH2 --;
R6 and R7 are independently hydrogen or an alkyl containing from 1 to 8 carbon atoms;
R8 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. - View Dependent Claims (27)
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28. A device made from an aliphatic polyoxaester comprising a first divalent repeating unit of formula I:
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space="preserve" listing-type="equation">[O--C(O)--C(R.sub.1)(R.sub.2 (O)(R.sub.3)--O--C(R.sub.1)(R.sub.2)--C(O)--]Iand two second repeating unit selected from the group of formulas consisting of;
space="preserve" listing-type="equation">[--O--R.sub.3 --C(O)--].sub.B, III
space="preserve" listing-type="equation">([--O--R.sub.13 --C(O)].sub.P --O--).sub.L G XIwherein R1 and R2 are independently hydrogen or an alkyl group containing 1 to 8 carbon atoms;
R3 is an alkylene unit or is an oxyalkylene group of the following formula;
space="preserve" listing-type="equation">--[(CH.sub.2).sub.C --O--].sub.D --(CH.sub.2).sub.E -- IVwherein 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;
R5 and R13 are different and are selected from the group consisting of --C(R6)(R7)--, --(CH2)3 --O--, --CH2 --CH2 --O--CH2 --, --CR8 H--CH2 --, --(CH2)5 --, (CH2)8 --O--C(O)-- and --(CH2)K --C(O)--CH2 --;
R6 and R7 are independently hydrogen or an alkyl containing from 1 to 8 carbon atoms;
R8 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. - View Dependent Claims (29)
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30. A device coated with an absorbable coating comprising an aliphatic polyoxaester having a first divalent repeating unit of formula I:
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space="preserve" listing-type="equation">[O--C(O)--C(R.sub.1)(R.sub.2)--O--(R.sub.3)--O--C(R.sub.1)(R.sub.2)--C(O)--]Iand two second repeating unit of the formulas;
space="preserve" listing-type="equation">[--O--R.sub.5 --C(O)--].sub.B, III
space="preserve" listing-type="equation">([--O--R.sub.13 --C(O)].sub.P --O--).sub.L G XIwherein R1 and R2 are independently hydrogen or an alkyl group containing 1 to 8 carbon atoms;
R3 is an alkylene unit or is an oxyalkylene group of the following formula;
space="preserve" listing-type="equation">--[(CH.sub.2).sub.C --O--].sub.D --(CH.sub.E -- IVwherein 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;
R5 and R13 are different and are selected from the group consisting of --C(R6)(R7)--, --(CH2)3 --O--, --CH2 --CH2 --O--CH2 --, --CR8 H--CH2 --, --(CH2)5 --, --(CH2)F --O--C(O)-- and --(CH2)K --C(O)--CH2 --;
R6 and R7 are independently hydrogen or an alkyl containing from 1 to 8 carbon atoms;
R8 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°
C. - View Dependent Claims (31)
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32. A drug delivery matrix comprising a drug and an aliphatic polyoxaester having a first divalent repeating unit of formula I:
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space="preserve" listing-type="equation">[O--C(O)--C(R.sub.1)(R.sub.2)--O--(R.sub.3)--O--C(R.sub.1)(R.sub.2)--C(O)--]Iand two second repeating unit of the formulas;
space="preserve" listing-type="equation">[--O--R.sub.5 --C(O)--].sub.B, III
space="preserve" listing-type="equation">([--O--R.sub.13 C(O)].sub.P --O--).sub.L G XIwherein R1 and R2 are independently hydrogen or an alkyl group containing 1 to 8 carbon atoms;
R3 is an alkylene unit or is an oxyalkylene group of the following formula;
space="preserve" listing-type="equation">--[(CH.sub.2).sub.C --O--].sub.D --(CH.sub.2).sub.E -- IVwherein 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;
R5 and R13 are different and are selected from the group consisting of --C(R6)(R7)--, --(CH2)3 --O--, --CH2 --CH2 --O--CH2 --, --CR8 H--CH2 --, --(CH2)5 --, --(CH2)F --O--C(O)-- and --(CH2)K --C(O)--CH2 --;
R6 and R7 are independently hydrogen or an alkyl containing from 1 to 8 carbon atoms;
R8 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°
C. - View Dependent Claims (33)
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Specification