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US 2012/0059117 A1Published application
Compounds for the synthesis of biostable polyurethane, polyurea or polyurea urethane polymers
AssigneeIberhospitex, S.A.
InventorsLluis Duocastella Codina, Maria Molina, Ofir Arad, Jose Ignacio Borrell Bilbao, David Sanchez Garcia, Sofia Henriette Pettersson Salom
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Abstract
It comprises compounds which are derived from a drug or a substance with therapeutic properties, and useful as reagents for the synthesis of biostable polymers including said drug in their backbone, namely polyurethanes, polyureas or polyurea urethanes that are biocompatible and biostable. It also comprises the processes for preparing the compounds and the polymers, as well as to the use of these polymers for the manufacture of medical devices.
Claims19
A compound of formula (I) or a salt thereof,
- (X—S)m-D (I)
- wherein
- -D is a radical derived from a drug or an active metabolite of a drug susceptible to form at least an amide bond, an urea bond, a carbamate bond, an ether bond, a thioamide bond, a disulfide bond, a siloxane bond, a carbonate bond, an amine bond, or an ester bond with S;
- —S— is a biradical consisting of a branched or unbranched, saturated or unsaturated C2-C299 hydrocarbon chain, bonded for one extreme to radical X and for the other extreme susceptible to form at least an amide bond, an urea bond, a carbamate bond, an ether bond, a thioamide bond, a disulfide bond, a siloxane bond, a carbonate bond, an amine bond, or an ester bond with D, said hydrocarbon chain having at the extreme forming the bond with D an atom or group of atoms selected from the group consisting of an oxygen atom, a sulphur atom, a radical of formula NR2, or a radical of formula CO, said hydrocarbon chain optionally having one or more non-terminal carbon atoms replaced by an oxygen atom, a sulphur atom, or group of formula NR2, and wherein optionally at least one hydrogen atom of said hydrocarbon chain is substituted by at least one radical selected from the group consisting of an halogen or a C1-C8-alkyl radical;
- —R2 is a radical selected from the group consisting of hydrogen, and a linear or branched C1-C8-alkyl;
- —X is a radical selected from the group consisting of —NH2, NCO, and —OH;
- and
- m is an integer from 1 to 4,
- with the proviso that when m is 1, —S— is bonded for one extreme to radical X and for the other extreme it forms a bond selected from an urea bond, a carbamate bond, an ether bond, a thioamide bond, a disulfide bond, a siloxane bond, a carbonate bond and an amine bond with D, provided that when said bond is a carbamate bond, D is different from a peptide or polypeptide.
6 more elements
A process for preparing a polyurethane, a polyurea or a polyurea urethane polymer comprising the steps of:
- a) reacting an excess of a compound comprising at least two isocyanate groups with a compound comprising at least two OH groups to obtain a polyurethane compound;
- and
- b) mixing the compound obtained in step a) with at least one compound of formula (I)
- (X—S)m-D (I)
- wherein
- -D is a radical derived from a drug or an active metabolite of a drug susceptible to form at least an amide bond, an urea bond, a carbamate bond, an ether bond, a thioamide bond, a disulfide bond, a siloxane bond, a carbonate bond, an amine bond, or an ester bond with S;
- —S— is a biradical consisting of a branched or unbranched, saturated or unsaturated C1-C299 hydrocarbon chain, bonded for one extrem to radical X and for the other extrem susceptible to form at least an amide bond, an urea bond, a carbamate bond, an ether bond, a thioamide bond, a disulfide bond, a siloxane bond, a carbonate bond, an amine bond, or an ester bond with D, said hydrocarbon chain having at the extreme forming the bond with D an atom or group of atoms selected from the group consisting of an oxygen atom, a sulphur atom, a radical of formula NR2 or a radical of formula CO, said hydrocarbon chain optionally having one or more non-terminal carbon atoms replaced by an oxygen atom, a sulphur atom, or group of formula NR2, and wherein optionally at least one hydrogen atom of said hydrocarbon chain is substituted by at least one radical selected from the group consisting of an halogen or a C1-C8-alkyl radical;
- —R1 is a radical selected from the group consisting of hydrogen, and a linear or branched C1-C8 alkyl;
- —X is a radical selected from the group consisting of —NH2, NCO, and —OH;
- and
- m is an integer from 1 to 4.
8 more elements
Dependencies are inferred from the claim text.