DE60038010T2 - Hydrogel-formendes system mit hydrophoben und hydrophilen komponenten - Google Patents
Hydrogel-formendes system mit hydrophoben und hydrophilen komponenten Download PDFInfo
- Publication number
- DE60038010T2 DE60038010T2 DE60038010T DE60038010T DE60038010T2 DE 60038010 T2 DE60038010 T2 DE 60038010T2 DE 60038010 T DE60038010 T DE 60038010T DE 60038010 T DE60038010 T DE 60038010T DE 60038010 T2 DE60038010 T2 DE 60038010T2
- Authority
- DE
- Germany
- Prior art keywords
- hydrogel
- forming system
- hydrophobic
- macromer
- weight
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 230000002209 hydrophobic effect Effects 0.000 title claims abstract description 42
- 239000000017 hydrogel Substances 0.000 claims abstract description 116
- 229920002307 Dextran Polymers 0.000 claims abstract description 43
- 229920001477 hydrophilic polymer Polymers 0.000 claims abstract description 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 22
- 229920006037 cross link polymer Polymers 0.000 claims abstract description 17
- 229920001282 polysaccharide Polymers 0.000 claims abstract description 17
- 239000005017 polysaccharide Substances 0.000 claims abstract description 17
- 239000003814 drug Substances 0.000 claims abstract description 16
- 229940079593 drug Drugs 0.000 claims abstract description 15
- 229920002521 macromolecule Polymers 0.000 claims abstract description 12
- 238000010526 radical polymerization reaction Methods 0.000 claims abstract description 11
- 229920005615 natural polymer Polymers 0.000 claims abstract description 6
- 229920001059 synthetic polymer Polymers 0.000 claims abstract description 5
- 150000004676 glycans Chemical class 0.000 claims abstract 4
- 238000006243 chemical reaction Methods 0.000 claims description 45
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 claims description 42
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 28
- 150000002009 diols Chemical class 0.000 claims description 25
- 229920000747 poly(lactic acid) Polymers 0.000 claims description 23
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 claims description 22
- 229960000905 indomethacin Drugs 0.000 claims description 21
- HXBPYFMVGFDZFT-UHFFFAOYSA-N allyl isocyanate Chemical compound C=CCN=C=O HXBPYFMVGFDZFT-UHFFFAOYSA-N 0.000 claims description 18
- 102000004877 Insulin Human genes 0.000 claims description 15
- 108090001061 Insulin Proteins 0.000 claims description 15
- 229940125396 insulin Drugs 0.000 claims description 14
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 14
- 108090000623 proteins and genes Proteins 0.000 claims description 10
- 102000004169 proteins and genes Human genes 0.000 claims description 10
- 239000004626 polylactic acid Substances 0.000 claims description 7
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 6
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 6
- RBQRWNWVPQDTJJ-UHFFFAOYSA-N methacryloyloxyethyl isocyanate Chemical compound CC(=C)C(=O)OCCN=C=O RBQRWNWVPQDTJJ-UHFFFAOYSA-N 0.000 claims description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 4
- 229920003232 aliphatic polyester Polymers 0.000 claims description 4
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 claims description 4
- 229920001184 polypeptide Polymers 0.000 claims description 4
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims description 3
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 2
- 239000011976 maleic acid Substances 0.000 claims description 2
- UJPKMTDFFUTLGM-UHFFFAOYSA-N 1-aminoethanol Chemical group CC(N)O UJPKMTDFFUTLGM-UHFFFAOYSA-N 0.000 claims 1
- 229920000642 polymer Polymers 0.000 abstract description 24
- 150000001875 compounds Chemical class 0.000 abstract description 14
- 239000003795 chemical substances by application Substances 0.000 abstract description 8
- 238000013270 controlled release Methods 0.000 abstract description 8
- 125000004386 diacrylate group Chemical group 0.000 description 55
- JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 description 30
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 24
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 24
- 229940098773 bovine serum albumin Drugs 0.000 description 24
- 239000007858 starting material Substances 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- 230000008961 swelling Effects 0.000 description 17
- TWNIBLMWSKIRAT-VFUOTHLCSA-N levoglucosan Chemical group O[C@@H]1[C@@H](O)[C@H](O)[C@H]2CO[C@@H]1O2 TWNIBLMWSKIRAT-VFUOTHLCSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- 230000035484 reaction time Effects 0.000 description 14
- 238000006467 substitution reaction Methods 0.000 description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 150000004804 polysaccharides Chemical class 0.000 description 12
- 239000002904 solvent Substances 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 9
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 239000012975 dibutyltin dilaurate Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 8
- 239000012948 isocyanate Substances 0.000 description 8
- 150000002513 isocyanates Chemical class 0.000 description 8
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 8
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 7
- 239000006227 byproduct Substances 0.000 description 7
- 230000015556 catabolic process Effects 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 238000006731 degradation reaction Methods 0.000 description 7
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 229910019142 PO4 Inorganic materials 0.000 description 6
- 239000008366 buffered solution Substances 0.000 description 6
- 238000004132 cross linking Methods 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 6
- 239000010452 phosphate Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- 239000012456 homogeneous solution Substances 0.000 description 5
- 238000011534 incubation Methods 0.000 description 5
- 239000004810 polytetrafluoroethylene Substances 0.000 description 5
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 238000013459 approach Methods 0.000 description 4
- 230000001186 cumulative effect Effects 0.000 description 4
- 230000003247 decreasing effect Effects 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- 241000220317 Rosa Species 0.000 description 3
- -1 aminoethanoyl group Chemical group 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229920001610 polycaprolactone Polymers 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000001226 reprecipitation Methods 0.000 description 3
- OBBKULVUPYDMLI-JIZZDEOASA-N C(C=C)(=O)O.C(C=C)(=O)O.C([C@@H](O)C)(=O)O Chemical compound C(C=C)(=O)O.C(C=C)(=O)O.C([C@@H](O)C)(=O)O OBBKULVUPYDMLI-JIZZDEOASA-N 0.000 description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000012867 bioactive agent Substances 0.000 description 2
- 230000000975 bioactive effect Effects 0.000 description 2
- 238000006065 biodegradation reaction Methods 0.000 description 2
- 230000002051 biphasic effect Effects 0.000 description 2
- VJLOFJZWUDZJBX-UHFFFAOYSA-N bis(2-hydroxyethyl)azanium;chloride Chemical compound [Cl-].OCC[NH2+]CCO VJLOFJZWUDZJBX-UHFFFAOYSA-N 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- WUESWDIHTKHGQA-UHFFFAOYSA-N cyclohexylurea Chemical class NC(=O)NC1CCCCC1 WUESWDIHTKHGQA-UHFFFAOYSA-N 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 108700022423 fluorescein-isothiocyanated- insulin Proteins 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 150000002433 hydrophilic molecules Chemical class 0.000 description 2
- 229920001600 hydrophobic polymer Polymers 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000004632 polycaprolactone Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 2
- OMDQUFIYNPYJFM-XKDAHURESA-N (2r,3r,4s,5r,6s)-2-(hydroxymethyl)-6-[[(2r,3s,4r,5s,6r)-4,5,6-trihydroxy-3-[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methoxy]oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O[C@H]2[C@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)[C@H](O)[C@H](O)[C@H](O)O1 OMDQUFIYNPYJFM-XKDAHURESA-N 0.000 description 1
- DBTMGCOVALSLOR-DEVYUCJPSA-N (2s,3r,4s,5r,6r)-4-[(2s,3r,4s,5r,6r)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-6-(hydroxymethyl)oxane-2,3,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](CO)O[C@H](O)[C@@H]2O)O)O[C@H](CO)[C@H]1O DBTMGCOVALSLOR-DEVYUCJPSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- KYHQZNGJUGFTGR-LURJTMIESA-N 7-[(2s)-2-hydroxypropyl]-1,3-dimethylpurine-2,6-dione Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C[C@@H](O)C KYHQZNGJUGFTGR-LURJTMIESA-N 0.000 description 1
- 229920000945 Amylopectin Polymers 0.000 description 1
- 229920000856 Amylose Polymers 0.000 description 1
- 206010002556 Ankylosing Spondylitis Diseases 0.000 description 1
- 229920002101 Chitin Polymers 0.000 description 1
- 108010001682 Dextranase Proteins 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 102000003974 Fibroblast growth factor 2 Human genes 0.000 description 1
- 108090000379 Fibroblast growth factor 2 Proteins 0.000 description 1
- 229920000926 Galactomannan Polymers 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 201000005569 Gout Diseases 0.000 description 1
- 206010018634 Gouty Arthritis Diseases 0.000 description 1
- 102000000589 Interleukin-1 Human genes 0.000 description 1
- 108010002352 Interleukin-1 Proteins 0.000 description 1
- 229920001202 Inulin Polymers 0.000 description 1
- 229920001543 Laminarin Polymers 0.000 description 1
- 239000005717 Laminarin Substances 0.000 description 1
- HLFSDGLLUJUHTE-SNVBAGLBSA-N Levamisole Chemical compound C1([C@H]2CN3CCSC3=N2)=CC=CC=C1 HLFSDGLLUJUHTE-SNVBAGLBSA-N 0.000 description 1
- 229920000057 Mannan Polymers 0.000 description 1
- 108010014251 Muramidase Proteins 0.000 description 1
- 102000016943 Muramidase Human genes 0.000 description 1
- 108010062010 N-Acetylmuramoyl-L-alanine Amidase Proteins 0.000 description 1
- 108091034117 Oligonucleotide Proteins 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229920000954 Polyglycolide Polymers 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229920002988 biodegradable polymer Polymers 0.000 description 1
- 239000004621 biodegradable polymer Substances 0.000 description 1
- 239000003124 biologic agent Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000013267 controlled drug release Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000007515 enzymatic degradation Effects 0.000 description 1
- 229940088598 enzyme Drugs 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- MHMNJMPURVTYEJ-UHFFFAOYSA-N fluorescein-5-isothiocyanate Chemical compound O1C(=O)C2=CC(N=C=S)=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 MHMNJMPURVTYEJ-UHFFFAOYSA-N 0.000 description 1
- SYTBZMRGLBWNTM-UHFFFAOYSA-N flurbiprofen Chemical compound FC1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-UHFFFAOYSA-N 0.000 description 1
- 229960002390 flurbiprofen Drugs 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000001415 gene therapy Methods 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 230000003914 insulin secretion Effects 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- JYJIGFIDKWBXDU-MNNPPOADSA-N inulin Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)OC[C@]1(OC[C@]2(OC[C@]3(OC[C@]4(OC[C@]5(OC[C@]6(OC[C@]7(OC[C@]8(OC[C@]9(OC[C@]%10(OC[C@]%11(OC[C@]%12(OC[C@]%13(OC[C@]%14(OC[C@]%15(OC[C@]%16(OC[C@]%17(OC[C@]%18(OC[C@]%19(OC[C@]%20(OC[C@]%21(OC[C@]%22(OC[C@]%23(OC[C@]%24(OC[C@]%25(OC[C@]%26(OC[C@]%27(OC[C@]%28(OC[C@]%29(OC[C@]%30(OC[C@]%31(OC[C@]%32(OC[C@]%33(OC[C@]%34(OC[C@]%35(OC[C@]%36(O[C@@H]%37[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O%37)O)[C@H]([C@H](O)[C@@H](CO)O%36)O)[C@H]([C@H](O)[C@@H](CO)O%35)O)[C@H]([C@H](O)[C@@H](CO)O%34)O)[C@H]([C@H](O)[C@@H](CO)O%33)O)[C@H]([C@H](O)[C@@H](CO)O%32)O)[C@H]([C@H](O)[C@@H](CO)O%31)O)[C@H]([C@H](O)[C@@H](CO)O%30)O)[C@H]([C@H](O)[C@@H](CO)O%29)O)[C@H]([C@H](O)[C@@H](CO)O%28)O)[C@H]([C@H](O)[C@@H](CO)O%27)O)[C@H]([C@H](O)[C@@H](CO)O%26)O)[C@H]([C@H](O)[C@@H](CO)O%25)O)[C@H]([C@H](O)[C@@H](CO)O%24)O)[C@H]([C@H](O)[C@@H](CO)O%23)O)[C@H]([C@H](O)[C@@H](CO)O%22)O)[C@H]([C@H](O)[C@@H](CO)O%21)O)[C@H]([C@H](O)[C@@H](CO)O%20)O)[C@H]([C@H](O)[C@@H](CO)O%19)O)[C@H]([C@H](O)[C@@H](CO)O%18)O)[C@H]([C@H](O)[C@@H](CO)O%17)O)[C@H]([C@H](O)[C@@H](CO)O%16)O)[C@H]([C@H](O)[C@@H](CO)O%15)O)[C@H]([C@H](O)[C@@H](CO)O%14)O)[C@H]([C@H](O)[C@@H](CO)O%13)O)[C@H]([C@H](O)[C@@H](CO)O%12)O)[C@H]([C@H](O)[C@@H](CO)O%11)O)[C@H]([C@H](O)[C@@H](CO)O%10)O)[C@H]([C@H](O)[C@@H](CO)O9)O)[C@H]([C@H](O)[C@@H](CO)O8)O)[C@H]([C@H](O)[C@@H](CO)O7)O)[C@H]([C@H](O)[C@@H](CO)O6)O)[C@H]([C@H](O)[C@@H](CO)O5)O)[C@H]([C@H](O)[C@@H](CO)O4)O)[C@H]([C@H](O)[C@@H](CO)O3)O)[C@H]([C@H](O)[C@@H](CO)O2)O)[C@@H](O)[C@H](O)[C@@H](CO)O1 JYJIGFIDKWBXDU-MNNPPOADSA-N 0.000 description 1
- 229940029339 inulin Drugs 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 229960001614 levamisole Drugs 0.000 description 1
- AIHDCSAXVMAMJH-GFBKWZILSA-N levan Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)OC[C@@H]1[C@@H](O)[C@H](O)[C@](CO)(CO[C@@H]2[C@H]([C@H](O)[C@@](O)(CO)O2)O)O1 AIHDCSAXVMAMJH-GFBKWZILSA-N 0.000 description 1
- 229960000274 lysozyme Drugs 0.000 description 1
- 239000004325 lysozyme Substances 0.000 description 1
- 235000010335 lysozyme Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000006174 pH buffer Substances 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 238000002464 physical blending Methods 0.000 description 1
- 239000006069 physical mixture Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 1
- 229960005205 prednisolone Drugs 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 229960004767 proxyphylline Drugs 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000002352 surface water Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 229920001221 xylan Polymers 0.000 description 1
- 150000004823 xylans Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
- C08L5/02—Dextran; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
- C08B37/0021—Dextran, i.e. (alpha-1,4)-D-glucan; Derivatives thereof, e.g. Sephadex, i.e. crosslinked dextran
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/64—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63
- C08G18/6484—Polysaccharides and derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/81—Unsaturated isocyanates or isothiocyanates
- C08G18/8108—Unsaturated isocyanates or isothiocyanates having only one isocyanate or isothiocyanate group
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/06—Unsaturated polyesters
- C08L67/07—Unsaturated polyesters having terminal carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2210/00—Compositions for preparing hydrogels
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S525/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S525/937—Utility as body contact e.g. implant, contact lens or I.U.D.
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- General Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Materials Engineering (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Hematology (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Materials For Medical Uses (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Colloid Chemistry (AREA)
- Graft Or Block Polymers (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12880399P | 1999-04-12 | 1999-04-12 | |
| US128803P | 1999-04-12 | ||
| PCT/US2000/006416 WO2000060956A1 (en) | 1999-04-12 | 2000-03-20 | Hydrogel-forming system with hydrophobic and hydrophilic components |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60038010D1 DE60038010D1 (de) | 2008-03-27 |
| DE60038010T2 true DE60038010T2 (de) | 2009-03-05 |
Family
ID=22437052
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60038010T Expired - Lifetime DE60038010T2 (de) | 1999-04-12 | 2000-03-20 | Hydrogel-formendes system mit hydrophoben und hydrophilen komponenten |
Country Status (10)
| Country | Link |
|---|---|
| US (4) | US6388047B1 (enExample) |
| EP (1) | EP1168934B1 (enExample) |
| JP (1) | JP4558213B2 (enExample) |
| AT (1) | ATE386075T1 (enExample) |
| AU (1) | AU3877200A (enExample) |
| CA (1) | CA2368617C (enExample) |
| DE (1) | DE60038010T2 (enExample) |
| DK (1) | DK1168934T3 (enExample) |
| ES (1) | ES2298135T3 (enExample) |
| WO (1) | WO2000060956A1 (enExample) |
Families Citing this family (83)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE60038010T2 (de) | 1999-04-12 | 2009-03-05 | Cornell Research Foundation, Inc. | Hydrogel-formendes system mit hydrophoben und hydrophilen komponenten |
| US6716445B2 (en) | 1999-04-12 | 2004-04-06 | Cornell Research Foundation, Inc. | Hydrogel entrapping therapeutic agent and stent with coating comprising this |
| CA2450123C (en) * | 2001-08-02 | 2013-01-29 | Cornell Research Foundation, Inc. | Biodegradable polyhydric alcohol esters |
| US20050064587A1 (en) * | 2001-09-07 | 2005-03-24 | Lawrence Rosenberg | Pancreatic small cells and uses thereof |
| US7037983B2 (en) | 2002-06-14 | 2006-05-02 | Kimberly-Clark Worldwide, Inc. | Methods of making functional biodegradable polymers |
| JP3742842B2 (ja) * | 2002-06-17 | 2006-02-08 | 独立行政法人産業技術総合研究所 | 生分解性ポリ乳酸樹脂組成物 |
| ES2424348T3 (es) * | 2002-06-24 | 2013-10-01 | Incept, Llc | Cargas y métodos para desplazar tejidos para mejorar los resultados radiológicos |
| AU2002950340A0 (en) | 2002-07-23 | 2002-09-12 | Commonwealth Scientific And Industrial Research Organisation | Biodegradable polyurethane/urea compositions |
| EP1530600B1 (en) * | 2002-08-09 | 2007-03-14 | Ottawa Health Research Institute | Bio-synthetic matrix and uses thereof |
| BR0314266A (pt) * | 2002-09-13 | 2005-07-26 | Ocular Sciences Inc | Dispositivos e métodos para a melhora de visão |
| WO2004064816A1 (en) * | 2003-01-16 | 2004-08-05 | Cornell Research Foundation, Inc. | PARTIALLY BIODEGRADABLE TEMPERATURE AND pH SENSITIVE HYDROGEL |
| US8545830B2 (en) * | 2003-03-24 | 2013-10-01 | University Of Tennessee Research Foundation | Multi-functional polymeric materials and their uses |
| WO2005041987A1 (en) * | 2003-10-29 | 2005-05-12 | Gentis, Inc. | Polymerizable emulsions for tissue engineering |
| ATE524203T1 (de) * | 2003-11-03 | 2011-09-15 | Medtronic Inc | Hydrogel für zellspezifisches einwachsen |
| MY144221A (en) * | 2004-03-03 | 2011-08-15 | Polynovo Biomaterials Pty Ltd | Biocompatible polymer compositions for dual or multistaged curing. |
| EP1735378A1 (en) * | 2004-03-17 | 2006-12-27 | Ciphergen Biosystems, Inc. | Photocrosslinked hydrogel blend surface coatings |
| JP2007530169A (ja) | 2004-03-26 | 2007-11-01 | サーモディクス，インコーポレイティド | 生物適合性表面を調製するための組成物及び方法 |
| GB0407661D0 (en) * | 2004-04-03 | 2004-05-05 | Univ Hull | Liquid crystalline interpenetrating polymer networks |
| JP4599550B2 (ja) * | 2004-04-09 | 2010-12-15 | 国立大学法人 東京医科歯科大学 | ナノゲル工学によるハイブリッドゲルの調製とバイオマテリアル応用 |
| US8241655B2 (en) * | 2004-05-12 | 2012-08-14 | Surmodics, Inc. | Coatings for medical articles including natural biodegradable polysaccharides |
| CA2566961A1 (en) | 2004-05-20 | 2005-12-08 | Coopervision, Inc. | Corneal onlays and wavefront aberration correction to enhance vision |
| US7446131B1 (en) | 2004-06-10 | 2008-11-04 | The United States Of America As Represented By The Secretary Of Agriculture | Porous polymeric matrices made of natural polymers and synthetic polymers and optionally at least one cation and methods of making |
| US8246993B2 (en) | 2004-06-10 | 2012-08-21 | Cytogel Pharma, Llc | Advantageous hydrogel composition |
| US20060013886A1 (en) | 2004-06-28 | 2006-01-19 | Daqing Wu | Injectable microspheres |
| US7235592B2 (en) * | 2004-10-12 | 2007-06-26 | Zimmer Gmbh | PVA hydrogel |
| AU2006216655B2 (en) * | 2005-02-23 | 2012-05-31 | Zimmer Technology, Inc. | Blend hydrogels and methods of making |
| US20060222596A1 (en) | 2005-04-01 | 2006-10-05 | Trivascular, Inc. | Non-degradable, low swelling, water soluble radiopaque hydrogel polymer |
| WO2007033418A1 (en) | 2005-09-20 | 2007-03-29 | Polynovo Biomaterials Pty Limited | Chain extenders |
| WO2007040557A1 (en) * | 2005-09-21 | 2007-04-12 | Surmodics, Inc. | Coatings and articles including natural biodegradable polysaccharides |
| ATE454908T1 (de) * | 2005-09-21 | 2010-01-15 | Surmodics Inc | In situ okklusionszusammensetzungen mit natürlichen biologisch abbaubaren polysacchariden |
| US20070098799A1 (en) * | 2005-10-28 | 2007-05-03 | Zimmer, Inc. | Mineralized Hydrogels and Methods of Making and Using Hydrogels |
| CA2632120C (en) * | 2005-12-07 | 2014-07-08 | Zimmer, Inc. | Methods of bonding or modifying hydrogels using irradiation |
| US20070141108A1 (en) * | 2005-12-20 | 2007-06-21 | Zimmer, Inc. | Fiber-reinforced water-swellable articles |
| EP1801135B1 (en) * | 2005-12-22 | 2010-09-29 | Zimmer Inc. | Perfluorocyclobutane crosslinked hydrogels |
| WO2007092550A2 (en) * | 2006-02-08 | 2007-08-16 | Coopervision Inc. | Corneal onlays and related methods |
| EP1999160B1 (en) * | 2006-03-14 | 2009-12-30 | Novozymes Biopharma DK A/S | Acrylated hyaluronic acid |
| US8110242B2 (en) * | 2006-03-24 | 2012-02-07 | Zimmer, Inc. | Methods of preparing hydrogel coatings |
| US8795709B2 (en) | 2006-03-29 | 2014-08-05 | Incept Llc | Superabsorbent, freeze dried hydrogels for medical applications |
| US20070232762A1 (en) * | 2006-03-31 | 2007-10-04 | Depuy Products, Inc. | Bearing material of medical implant having reduced wear rate and method for reducing wear rate |
| US7812098B2 (en) * | 2006-03-31 | 2010-10-12 | Depuy Products, Inc. | Bearing material of medical implant having reduced wear rate and method for reducing wear rate |
| US7883520B2 (en) * | 2006-04-10 | 2011-02-08 | Forsight Labs, Llc | Corneal epithelial pocket formation systems, components and methods |
| US7872068B2 (en) * | 2006-05-30 | 2011-01-18 | Incept Llc | Materials formable in situ within a medical device |
| CN101522788B (zh) * | 2006-08-02 | 2013-04-10 | 宝利诺沃生物材料有限公司 | 生物相容性聚合物组合物 |
| US20080075785A1 (en) * | 2006-09-22 | 2008-03-27 | San-Laung Chow | Controlled release hydrogel formulation |
| US20110165236A1 (en) * | 2006-09-22 | 2011-07-07 | Biokey, Inc. | Controlled release hydrogel formulation |
| US20080154241A1 (en) * | 2006-12-07 | 2008-06-26 | Burkstrand Michael J | Latent stabilization of bioactive agents releasable from implantable medical articles |
| US9125807B2 (en) | 2007-07-09 | 2015-09-08 | Incept Llc | Adhesive hydrogels for ophthalmic drug delivery |
| US7731988B2 (en) * | 2007-08-03 | 2010-06-08 | Zimmer, Inc. | Multi-polymer hydrogels |
| US20090043398A1 (en) * | 2007-08-09 | 2009-02-12 | Zimmer, Inc. | Method of producing gradient articles by centrifugation molding or casting |
| US20110136935A1 (en) * | 2007-08-30 | 2011-06-09 | National University Of Singapore | Bone and/or dental cement composition and uses thereof |
| US8062739B2 (en) * | 2007-08-31 | 2011-11-22 | Zimmer, Inc. | Hydrogels with gradient |
| WO2009043099A1 (en) * | 2007-10-03 | 2009-04-09 | Polynovo Biomaterials Limited | High modulus polyurethane and polyurethane/urea compositions |
| US7947784B2 (en) | 2007-11-16 | 2011-05-24 | Zimmer, Inc. | Reactive compounding of hydrogels |
| US8034362B2 (en) * | 2008-01-04 | 2011-10-11 | Zimmer, Inc. | Chemical composition of hydrogels for use as articulating surfaces |
| EP2271379B1 (en) | 2008-03-28 | 2015-11-25 | SurModics, Inc. | Insertable medical devices having microparticulate-associated elastic substrates and methods for drug delivery |
| EP2296630A2 (en) | 2008-05-07 | 2011-03-23 | SurModics, Inc. | Delivery of nucleic acid complexes from particles |
| US20100087920A1 (en) * | 2008-10-07 | 2010-04-08 | Forsight Labs, Llc | Corneal Onlay Lenses and Related Methods for Improving Vision of Presbyopic Patients |
| US8409606B2 (en) | 2009-02-12 | 2013-04-02 | Incept, Llc | Drug delivery through hydrogel plugs |
| CA2977830C (en) | 2009-05-04 | 2019-09-17 | Incept, Llc | Biomaterials for track and puncture closure |
| JP2012235797A (ja) | 2009-09-18 | 2012-12-06 | Terumo Corp | ステント |
| NZ599524A (en) | 2009-11-09 | 2014-04-30 | Spotlight Technology Partners Llc | Polysaccharide based hydrogels |
| WO2011057133A1 (en) | 2009-11-09 | 2011-05-12 | Spotlight Technology Partners Llc | Fragmented hydrogels |
| EP3960215B1 (en) | 2009-12-15 | 2024-10-16 | Incept, LLC | Implants and biodegradable fiducial markers |
| EP2574172A4 (en) | 2010-05-21 | 2013-10-30 | Cytogel Pharma Llc | MATERIALS AND METHOD FOR TREATING INFLAMMATION |
| US8961501B2 (en) | 2010-09-17 | 2015-02-24 | Incept, Llc | Method for applying flowable hydrogels to a cornea |
| US8901092B2 (en) | 2010-12-29 | 2014-12-02 | Surmodics, Inc. | Functionalized polysaccharides for active agent delivery |
| EP3081937B1 (en) | 2011-07-18 | 2019-11-13 | President and Fellows of Harvard College | Engineered microbe-targeting molecules and uses thereof |
| US10226417B2 (en) | 2011-09-16 | 2019-03-12 | Peter Jarrett | Drug delivery systems and applications |
| RU2521194C2 (ru) * | 2011-11-16 | 2014-06-27 | Общество с ограниченной ответственностью предприятие "Репер" | Матрица для клеточной трансплантологии |
| CN109200013A (zh) | 2011-12-05 | 2019-01-15 | 因赛普特有限责任公司 | 医用有机凝胶方法和组合物 |
| BR112015024703A2 (pt) * | 2013-03-27 | 2017-07-18 | Centre Hospitalier Univ Vaudois C H U V | formulação farmacêutica, método de tratamento e/ou prevenção de restenose e kit para o tratamento e/ou prevenção de restenose |
| EP3848045A1 (en) | 2013-05-21 | 2021-07-14 | President and Fellows of Harvard College | Engineered heme-binding compositions and uses thereof |
| WO2015095604A2 (en) | 2013-12-18 | 2015-06-25 | President And Fellows Of Harvard College | Methods and assays relating to circulating tumor cells |
| US10519443B2 (en) | 2014-09-08 | 2019-12-31 | University Of Iowa Research Foundation | Microrna inhibitor system and methods of use thereof |
| CN108289928B (zh) | 2015-08-06 | 2024-09-17 | 哈佛大学校长及研究员协会 | 改进的微生物-结合分子和其用途 |
| US10273476B2 (en) | 2016-04-30 | 2019-04-30 | University Of Iowa Research Foundation | MicroRNA-200 based approaches for modulating bone formation inhibition and bone regeneration |
| MX2019006868A (es) * | 2016-12-16 | 2019-09-23 | Du Pont | Derivados de polisacáridos anfifílicos y composiciones que los comprenden. |
| CN106913915B (zh) * | 2017-04-21 | 2019-05-31 | 浙江大学 | 一种自愈合支架复合涂层及其制备方法和应用 |
| CN107216450B (zh) * | 2017-04-21 | 2019-06-11 | 浙江大学 | 一种自愈合抗菌涂层及其制备方法和应用 |
| US10975121B2 (en) | 2017-06-24 | 2021-04-13 | Cytogel Pharma, Llc | Analgesic mu-opioid receptor binding peptide pharmaceutical formulations and uses thereof |
| CN110108537B (zh) * | 2018-02-01 | 2020-08-25 | 中国科学技术大学 | 一种用于生物组织包埋的包埋剂和包埋方法 |
| CN108359054A (zh) * | 2018-02-10 | 2018-08-03 | 西北大学 | 一种葡萄糖敏感型全互穿网络水凝胶及其制备方法 |
| CN116496475B (zh) * | 2023-06-26 | 2023-09-22 | 海杰亚（北京）医疗器械有限公司 | 用于栓塞微球的可降解交联剂、可降解栓塞微球及其制备方法和药物组合物 |
Family Cites Families (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4002173A (en) | 1974-07-23 | 1977-01-11 | International Paper Company | Diester crosslinked polyglucan hydrogels and reticulated sponges thereof |
| US4032488A (en) * | 1975-10-03 | 1977-06-28 | Meito Sangyo Kabushiki Kaisha | Dextran ester-olefin compound copolymer and process for preparing same |
| SU729197A1 (ru) * | 1977-07-05 | 1980-04-25 | Ордена Ленина Институт Элементоорганических Соединений Ан Ссср | Сшитые сополимеры хитозана |
| US4277582A (en) * | 1978-03-03 | 1981-07-07 | Ciba-Geigy Corporation | Water-insoluble hydrophilic copolymers |
| GB8418772D0 (en) | 1984-07-24 | 1984-08-30 | Geistlich Soehne Ag | Chemical substances |
| US4857602A (en) * | 1986-09-05 | 1989-08-15 | American Cyanamid Company | Bioabsorbable surgical suture coating |
| US4938763B1 (en) | 1988-10-03 | 1995-07-04 | Atrix Lab Inc | Biodegradable in-situ forming implants and method of producing the same |
| US5410016A (en) * | 1990-10-15 | 1995-04-25 | Board Of Regents, The University Of Texas System | Photopolymerizable biodegradable hydrogels as tissue contacting materials and controlled-release carriers |
| US5529914A (en) * | 1990-10-15 | 1996-06-25 | The Board Of Regents The Univeristy Of Texas System | Gels for encapsulation of biological materials |
| US5626863A (en) | 1992-02-28 | 1997-05-06 | Board Of Regents, The University Of Texas System | Photopolymerizable biodegradable hydrogels as tissue contacting materials and controlled-release carriers |
| US5210111A (en) * | 1991-08-22 | 1993-05-11 | Ciba-Geigy Corporation | Crosslinked hydrogels derived from hydrophilic polymer backbones |
| US5837747A (en) | 1991-10-29 | 1998-11-17 | Vivorx, Inc. | Crosslinkable polysaccharides, polycations and lipids useful for encapsulation and drug release |
| WO1993016176A1 (en) | 1992-02-13 | 1993-08-19 | Bio-Metric Systems, Inc. | Immobilization of chemical species in crosslinked matrices |
| BR9306038A (pt) | 1992-02-28 | 1998-01-13 | Univ Texas | Hidrogéis biodegradáveis fotopolimerizáveis como materiais de contato de tecidos e condutores de liberação controlada |
| US5573934A (en) * | 1992-04-20 | 1996-11-12 | Board Of Regents, The University Of Texas System | Gels for encapsulation of biological materials |
| IT1260154B (it) | 1992-07-03 | 1996-03-28 | Lanfranco Callegaro | Acido ialuronico e suoi derivati in polimeri interpenetranti (ipn) |
| US5514379A (en) | 1992-08-07 | 1996-05-07 | The General Hospital Corporation | Hydrogel compositions and methods of use |
| NZ258533A (en) | 1992-11-30 | 1996-08-27 | Ciba Geigy Ag | Vinyl ester and amide derivatives of a dicarboxylic acid cyclic-oligomeric carbohydrate half ester; use for forming contact lenses, as thickeners, surfactants and lens cleaning agents |
| KR0141431B1 (ko) | 1994-05-17 | 1998-07-01 | 김상웅 | 생분해성 하이드로겔 고분자 |
| TW291481B (en) * | 1994-10-27 | 1996-11-21 | Novartis Erfind Verwalt Gmbh | Poly-unsaturated carbohydrate derivatives, polymers thereof and their use |
| US5607686A (en) | 1994-11-22 | 1997-03-04 | United States Surgical Corporation | Polymeric composition |
| US5540929A (en) | 1995-03-08 | 1996-07-30 | Board Of Trustees Operating Michigan State University | Polysaccharides grafted with aliphatic polyesters derived from cyclic esters |
| US5900245A (en) | 1996-03-22 | 1999-05-04 | Focal, Inc. | Compliant tissue sealants |
| CA2228118A1 (en) * | 1995-07-28 | 1997-02-13 | Focal, Inc. | Multiblock biodegradable hydrogels for use as controlled release agents for drugs delivery and tissue treatments agents |
| JP3572144B2 (ja) * | 1996-05-31 | 2004-09-29 | 名糖産業株式会社 | デキストランエステル共重合体 |
| US5854382A (en) * | 1997-08-18 | 1998-12-29 | Meadox Medicals, Inc. | Bioresorbable compositions for implantable prostheses |
| WO1999011692A1 (en) * | 1997-09-03 | 1999-03-11 | The Regents Of The University Of California | Novel biomimetic hydrogel materials |
| ATE297440T1 (de) * | 1998-08-31 | 2005-06-15 | Cornell Res Foundation Inc | Dextran-maleinsäuremonoester und hydrogele daraus |
| DE60038010T2 (de) | 1999-04-12 | 2009-03-05 | Cornell Research Foundation, Inc. | Hydrogel-formendes system mit hydrophoben und hydrophilen komponenten |
| US6716445B2 (en) | 1999-04-12 | 2004-04-06 | Cornell Research Foundation, Inc. | Hydrogel entrapping therapeutic agent and stent with coating comprising this |
| US6388035B1 (en) * | 1999-09-02 | 2002-05-14 | Alcon Universal Ltd. | Hydrophobically-bound, hydrophilic coating compositions for surgical implants |
| US6503538B1 (en) | 2000-08-30 | 2003-01-07 | Cornell Research Foundation, Inc. | Elastomeric functional biodegradable copolyester amides and copolyester urethanes |
| CA2450123C (en) | 2001-08-02 | 2013-01-29 | Cornell Research Foundation, Inc. | Biodegradable polyhydric alcohol esters |
-
2000
- 2000-03-20 DE DE60038010T patent/DE60038010T2/de not_active Expired - Lifetime
- 2000-03-20 EP EP00917865A patent/EP1168934B1/en not_active Expired - Lifetime
- 2000-03-20 DK DK00917865T patent/DK1168934T3/da active
- 2000-03-20 JP JP2000610306A patent/JP4558213B2/ja not_active Expired - Fee Related
- 2000-03-20 US US09/531,451 patent/US6388047B1/en not_active Expired - Lifetime
- 2000-03-20 CA CA2368617A patent/CA2368617C/en not_active Expired - Fee Related
- 2000-03-20 ES ES00917865T patent/ES2298135T3/es not_active Expired - Lifetime
- 2000-03-20 AT AT00917865T patent/ATE386075T1/de not_active IP Right Cessation
- 2000-03-20 WO PCT/US2000/006416 patent/WO2000060956A1/en not_active Ceased
- 2000-03-20 AU AU38772/00A patent/AU3877200A/en not_active Abandoned
-
2002
- 2002-03-13 US US10/096,435 patent/US6583219B2/en not_active Expired - Fee Related
-
2003
- 2003-02-21 US US10/369,676 patent/US6709668B2/en not_active Expired - Fee Related
- 2003-12-12 US US10/733,291 patent/US6916857B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DE60038010D1 (de) | 2008-03-27 |
| CA2368617A1 (en) | 2000-10-19 |
| JP4558213B2 (ja) | 2010-10-06 |
| JP2002541308A (ja) | 2002-12-03 |
| US20040122165A1 (en) | 2004-06-24 |
| US20020161169A1 (en) | 2002-10-31 |
| AU3877200A (en) | 2000-11-14 |
| CA2368617C (en) | 2010-03-16 |
| US6709668B2 (en) | 2004-03-23 |
| US6583219B2 (en) | 2003-06-24 |
| EP1168934A4 (en) | 2004-12-08 |
| DK1168934T3 (da) | 2008-05-13 |
| ATE386075T1 (de) | 2008-03-15 |
| US6388047B1 (en) | 2002-05-14 |
| ES2298135T3 (es) | 2008-05-16 |
| US20030125509A1 (en) | 2003-07-03 |
| EP1168934A1 (en) | 2002-01-09 |
| EP1168934B1 (en) | 2008-02-13 |
| WO2000060956A1 (en) | 2000-10-19 |
| US6916857B2 (en) | 2005-07-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE60038010T2 (de) | Hydrogel-formendes system mit hydrophoben und hydrophilen komponenten | |
| DE69938612T2 (de) | Funktionelle chitosanderivate | |
| DE69310396T2 (de) | Photohärtbare Derivate von Glykosaminoglykan, vernetzte Glykosaminoglykane und Verfahren zu deren Herstellung | |
| DE60316291T2 (de) | Esterderivate von hyaluronsäure zur herstellung von hydrogelmaterialien durch photohärtung | |
| DE3751647T2 (de) | Biologisch abbaubare Mikrokugeln als Träger für Makromoleküle | |
| DE2623056C2 (de) | Verfahren zur Herstellung von festen wasserunlöslichen, in Methanol löslichen, hydrophilen Polymeren | |
| DE69903351T3 (de) | Vernetzte hyaluronsäure und ihre medizinischen verwendungen | |
| DE69617277T2 (de) | Absorbierbare Polyalkylendiglycolate | |
| DE3855351T2 (de) | Wasserlösliche hyaluronsäurederivate | |
| DE69614391T2 (de) | Gelzusammensetzung auf basis von polysacchariden | |
| DE69809892T2 (de) | N-sulfatierte hyaluronsäureverbindungen, ihre derivate und verfahren zu ihrer herstellung | |
| DE60029761T2 (de) | Verfahren zur vernetzung von hyaluronsäure mit polymeren | |
| DE69914928T2 (de) | Polymerkomplexe von glukuronoglukanen | |
| DE69837443T3 (de) | Abbaubare polyethyleneglycolhydrogele mit kontrollierter halbwertzeit und ihre vorprodukte | |
| DE69925361T2 (de) | Vernetzbare macromere, die eine initiatorgruppe tragen | |
| EP0400283B1 (de) | Hydrophile quellfähige Pfropfpolymerisate, deren Herstellung und Verwendung | |
| DE60117502T2 (de) | Photohärtbare Derivate von Hyaluronsäure, Verfahren zu deren Herstellung, vernetztes und photogehärtetes Derivat der Hyaluronsäure und diese enthaltendes medizinisches Material | |
| DE69925757T2 (de) | Dextran-maleinsäuremonoester und hydrogele daraus | |
| DE3751938T2 (de) | Saure dekristallisierung von hochkristallin chitosan oder teilentacetylierten chitin | |
| DE69826119T2 (de) | Heteropolysaccharid-konjugate, halbinterpenetrierende polysaccharidgele und verfahren zu deren herstellung | |
| EP0703265A1 (de) | Hydrophile, hochquellfähige Hydrogele | |
| DE3128815A1 (de) | Polymeres verbundmaterial, seine herstellung und verwendung | |
| DE60010072T2 (de) | Stereokomplexe hydrogele | |
| DE4318094A1 (de) | Superabsorbentien und ein Verfahren zu ihrer Herstellung | |
| EP0316792A2 (de) | Hydrophile quellbare Pfropfpolymerisate, deren Herstellung und Verwendung |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition |