초록 ▼

The present invention relates to chain extenders, processes for their preparation and their use in the preparation of biocompatible biodegradable polyurethanes and polyurethane ureas for biomedical applications such as stents, scaffolds for tissue engineering. The chain extenders comprise a compound

The present invention relates to chain extenders, processes for their preparation and their use in the preparation of biocompatible biodegradable polyurethanes and polyurethane ureas for biomedical applications such as stents, scaffolds for tissue engineering. The chain extenders comprise a compound of formula (I)

대표청구항 ▼

1. A biocompatible biodegradable polyurethane or polyurethane urea comprising a segment formed from a chain extender, wherein the chain extender is a compound of formula (2): wherein R1 and R3 are independently selected from C1-20 alkylene and C2-20 alkenylene, at least one of which is substituted b

1. A biocompatible biodegradable polyurethane or polyurethane urea comprising a segment formed from a chain extender, wherein the chain extender is a compound of formula (2): wherein R1 and R3 are independently selected from C1-20 alkylene and C2-20 alkenylene, at least one of which is substituted by one or more groups selected from the group consisting of C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, aryl, halo, halo C1-6 alkyl, halo C2-6 alkenyl, halo C2-6 alkynyl, haloaryl, hydroxy, C1-6 alkoxy, C2-6 alkenyloxy, C1-6 aryloxy, benzyloxy, halo C1-6 alkoxy, haloalkenyloxy, haloaryloxy, nitro, nitroC1-6 alkyl, nitroC2-6 alkenyl, nitroC2-6 alkynyl, nitroaryl, nitroheterocyclyl, amino, C1-6 alkylamino, C1-6 dialkylamino, C2-6 alkenylamino, C2-6 alkynylamino, arylamino, diarylamino, benzylamino, dibenzylamino, acyl, alkenylacyl, alkynylacyl, arylacyl, acylamino, diacylamino, acyloxy, C1-6 alkylsulphonyloxy, arylsulphenyloxy, heterocyclyl, heterocyclyloxy, heterocyclylamino, haloheterocyclyl, C1-6 alkylsulphenyl, arylsulphenyl, carboalkoxy, carboaryloxy, mercapto, C1-6 alkylthio, benzylthio, acylthio and phosphorus-containing groups. 2. A biocompatible biodegradable polyurethane or polyurethane urea according to claim 1 wherein the aryl group is selected from the group consisting of phenyl, naphthyl, tetrahydronaphthyl, indane and biphenyl. 3. A biocompatible biodegradable polyurethane or polyurethane urea according to claim 1 wherein the heterocyclyl group is selected from the group consisting of unsaturated 3 to 6-membered heteromonocyclic groups containing 1 to 4 nitrogen atoms, saturated 3 to 6-membered heteromonocyclic groups containing 1 to 4 nitrogen atoms, unsaturated condensed heterocyclic groups containing 1 to 5 nitrogen atoms, unsaturated 3 to 6-membered heteromonocyclic groups containing an oxygen atom, unsaturated 3 to 6-membered heteromonocyclic group containing 1 to 2 sulphur atoms, unsaturated 3 to 6-membered heteromonocyclic group containing 1 to 2 oxygen atoms and 1 to 3 nitrogen atoms, saturated 3 to 6-membered heteromonocyclic group containing 1 to 2 oxygen atoms and 1 to 3 nitrogen atoms, unsaturated condensed heterocyclic group containing 1 to 2 oxygen atoms and 1 to 3 nitrogen atoms, unsaturated 3 to 6-membered heteromonocyclic group containing 1 to 2 sulphur atoms and 1 to 3 nitrogen atoms, saturated 3 to 6-membered heteromonocyclic group containing 1 to 2 sulphur atoms and 1 to 3 nitrogen atoms, and unsaturated condensed heterocyclic group containing 1 to 2 sulphur atoms and 1 to 3 nitrogen atoms. 4. A biocompatible biodegradable polyurethane or polyurethane urea according to claim 1 wherein the heterocyclyl group is selected from the group consisting of pyrrolyl, pyrrolinyl, imidazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazolyl, tetrazolyl, pyrrolidinyl, imidazolidinyl, piperidino, piperazinyl, indolyl, isoindolyl, indolizinyl, benzimidazolyl, quinolyl, isoquinolyl, indazolyl, benzotriazolyl, tetrazolopyridazinyl, pyranyl or furyl, thienyl, oxazolyl, isoxazolyl, oxadiazolyl, morpholinyl, benzoxazolyl, benzoxadiazolyl, thiazolyl, thiadiazolyl, thiazolidinyl, benzothiazolyl and benzothiadiazolyl. 5. A biocompatible biodegradable polyurethane or polyurethane urea according to claim 1 wherein at least one of the substituents of the C1-20 alkylene or C2-20 alkenylene groups of R1 or R3 comprises a bioactive moiety. 6. A biocompatible biodegradable polyurethane or polyurethane urea according to claim 1 comprising the chain extender of formula (2) and another chain extender. 7. A biocompatible biodegradable polyurethane or polyurethane urea according to claim 6, in which the other chain extender is a diol, dithiol, diamine, amino acid or dicarboxylic acid. 8. A biocompatible biodegradable polyurethane or polyurethane urea according to claim 1 which comprises a reaction product of an isocyanate, polyol and a chain extender. 9. A biocompatible polyurethane or polyurethane urea according to claim 8 in which the polyurethane or polyurethane urea is thermoplastic and of the general formula: in whichRx is from the isocyanate, Ry is from the chain extender and Rz is from the soft segment polyol;‘q’ is the average number of repeat units in the hard segment;‘r’ is the average number of repeat units in the soft segment; and‘s’ is proportional to the molecular weight of the polymer and includes both the hard segments repeat units and the soft segment;and in which ‘q’ is an integer between 1 and 100, ‘r’ is an integer between 0 and 100, and ‘s’ is an integer between 1 and 500. 10. A biocompatible polyurethane or polyurethane urea according to claim 8 in which the isocyanate is a diisocyanate. 11. A biocompatible polyurethane or polyurethane urea according to claim 8, in which the polyol is a diol, triol, tetrol, hexol or macrodiol. 12. A biocompatible polyurethane or polyurethane urea according to claim 8, in which the polyol is terminated by a hydroxyl, thiol or carboxylic acid group. 13. A biocompatible polyurethane or polyurethane urea according to claim 8, wherein the polyol is of general formula: wherein h and/or k are independently 0 or an integer, j is an integer, Z is a linear or branched alkyl, alkenyl or aryl wherein each occurrence of Z independently within the segment j may be the same or different and R is a linear or branched alkyl, alkenyl, aminoalkenyl, alkoxy or aryl function wherein each occurrence of R independently within the segments h or k may be the same or different, andwherein one or both of R and Z optionally comprises a bioactive moiety. 14. A biocompatible polyurethane or polyurethane urea according to claim 13, in which the polyol is selected from the group consisting of poly(ε-caprolactone) diol, MW 400: in which Z is (CH2—CH2), R is (CH2)5 and j=1 and (h+k)=2.96; (glycolic acid-ethylene glycol) dimer: in which Z is (CH2—CH2), R is (CH2), j=1 and (h+k)=1; and poly(ethylene glycol), MW 400: in which h=0, k=0, j=˜13 and R6 is (CH2—CH2). 15. A biocompatible polyurethane or polyurethane urea according to claim 8, in which the polyol has a molecular weight of 200-5000, 200-2000 or 200-1000.