CA2519503C - Drug delivery from a polymer coating on a medical device - Google Patents
Drug delivery from a polymer coating on a medical device Download PDFInfo
- Publication number
- CA2519503C CA2519503C CA2519503A CA2519503A CA2519503C CA 2519503 C CA2519503 C CA 2519503C CA 2519503 A CA2519503 A CA 2519503A CA 2519503 A CA2519503 A CA 2519503A CA 2519503 C CA2519503 C CA 2519503C
- Authority
- CA
- Canada
- Prior art keywords
- coating
- monomer unit
- copolymer
- layer
- methacrylate
- 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
- 238000000576 coating method Methods 0.000 title claims abstract description 200
- 239000011248 coating agent Substances 0.000 title claims abstract description 186
- 229920000642 polymer Polymers 0.000 title claims description 201
- 238000012377 drug delivery Methods 0.000 title description 4
- 239000000178 monomer Substances 0.000 claims abstract description 389
- 229920001577 copolymer Polymers 0.000 claims abstract description 248
- 230000009477 glass transition Effects 0.000 claims abstract description 146
- 238000000034 method Methods 0.000 claims abstract description 68
- 239000000203 mixture Substances 0.000 claims abstract description 68
- 229920001519 homopolymer Polymers 0.000 claims abstract description 66
- 239000003814 drug Substances 0.000 claims description 112
- 229940124597 therapeutic agent Drugs 0.000 claims description 100
- 229920000669 heparin Polymers 0.000 claims description 49
- 125000000524 functional group Chemical group 0.000 claims description 48
- 229960002897 heparin Drugs 0.000 claims description 46
- -1 poly (isocyanatoethyl Chemical group 0.000 claims description 45
- 229960001592 paclitaxel Drugs 0.000 claims description 42
- 229930012538 Paclitaxel Natural products 0.000 claims description 41
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims description 41
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 claims description 39
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 39
- 239000002904 solvent Substances 0.000 claims description 29
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 22
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 21
- 239000002202 Polyethylene glycol Substances 0.000 claims description 21
- 229920001223 polyethylene glycol Polymers 0.000 claims description 21
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 16
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 15
- 239000000155 melt Substances 0.000 claims description 14
- 230000008569 process Effects 0.000 claims description 14
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 13
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 13
- 239000007943 implant Substances 0.000 claims description 11
- 229920002554 vinyl polymer Polymers 0.000 claims description 11
- 230000003993 interaction Effects 0.000 claims description 9
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 9
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 9
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 9
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 9
- 229920002307 Dextran Polymers 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims description 8
- RBQRWNWVPQDTJJ-UHFFFAOYSA-N methacryloyloxyethyl isocyanate Chemical compound CC(=C)C(=O)OCCN=C=O RBQRWNWVPQDTJJ-UHFFFAOYSA-N 0.000 claims description 8
- 238000005507 spraying Methods 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 6
- 150000002576 ketones Chemical class 0.000 claims description 6
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 5
- 150000001540 azides Chemical class 0.000 claims description 5
- 238000000113 differential scanning calorimetry Methods 0.000 claims description 5
- 229910021653 sulphate ion Inorganic materials 0.000 claims description 5
- 230000001225 therapeutic effect Effects 0.000 claims description 5
- 230000002792 vascular Effects 0.000 claims description 5
- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical class CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 claims description 4
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims description 4
- AJXBTRZGLDTSST-UHFFFAOYSA-N amino 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)ON AJXBTRZGLDTSST-UHFFFAOYSA-N 0.000 claims description 4
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 4
- 238000007598 dipping method Methods 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 230000002209 hydrophobic effect Effects 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 4
- 150000002513 isocyanates Chemical class 0.000 claims description 4
- 230000004044 response Effects 0.000 claims description 4
- 125000001174 sulfone group Chemical group 0.000 claims description 4
- QRIMLDXJAPZHJE-UHFFFAOYSA-N 2,3-dihydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)CO QRIMLDXJAPZHJE-UHFFFAOYSA-N 0.000 claims description 3
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 3
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 3
- 150000001241 acetals Chemical class 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 3
- 150000001266 acyl halides Chemical class 0.000 claims description 3
- 150000001299 aldehydes Chemical class 0.000 claims description 3
- 150000001345 alkine derivatives Chemical class 0.000 claims description 3
- 150000001361 allenes Chemical class 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 150000001413 amino acids Chemical class 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- 150000001541 aziridines Chemical class 0.000 claims description 3
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 3
- 125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 claims description 3
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical class B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims description 3
- 229910000085 borane Inorganic materials 0.000 claims description 3
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 150000008049 diazo compounds Chemical class 0.000 claims description 3
- 230000002526 effect on cardiovascular system Effects 0.000 claims description 3
- 210000003709 heart valve Anatomy 0.000 claims description 3
- 150000001261 hydroxy acids Chemical class 0.000 claims description 3
- 150000002466 imines Chemical class 0.000 claims description 3
- 150000003951 lactams Chemical class 0.000 claims description 3
- 239000004005 microsphere Substances 0.000 claims description 3
- 150000002924 oxiranes Chemical class 0.000 claims description 3
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 3
- 229920000570 polyether Polymers 0.000 claims description 3
- 229920001451 polypropylene glycol Polymers 0.000 claims description 3
- 150000003456 sulfonamides Chemical class 0.000 claims description 3
- 150000003567 thiocyanates Chemical class 0.000 claims description 3
- RSPCKAHMRANGJZ-UHFFFAOYSA-N thiohydroxylamine Chemical class SN RSPCKAHMRANGJZ-UHFFFAOYSA-N 0.000 claims description 3
- 150000003573 thiols Chemical class 0.000 claims description 3
- YXMISKNUHHOXFT-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) prop-2-enoate Chemical compound C=CC(=O)ON1C(=O)CCC1=O YXMISKNUHHOXFT-UHFFFAOYSA-N 0.000 claims description 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 claims description 2
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims description 2
- 108010035532 Collagen Proteins 0.000 claims description 2
- 102000008186 Collagen Human genes 0.000 claims description 2
- 108010014258 Elastin Proteins 0.000 claims description 2
- 102000016942 Elastin Human genes 0.000 claims description 2
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 claims description 2
- 108010010803 Gelatin Proteins 0.000 claims description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 2
- 239000000020 Nitrocellulose Substances 0.000 claims description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 2
- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 claims description 2
- 229920001436 collagen Polymers 0.000 claims description 2
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 claims description 2
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 claims description 2
- 229920002549 elastin Polymers 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 229920002313 fluoropolymer Polymers 0.000 claims description 2
- 239000004811 fluoropolymer Substances 0.000 claims description 2
- 229920000159 gelatin Polymers 0.000 claims description 2
- 239000008273 gelatin Substances 0.000 claims description 2
- 235000019322 gelatine Nutrition 0.000 claims description 2
- 235000011852 gelatine desserts Nutrition 0.000 claims description 2
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 2
- 229920001477 hydrophilic polymer Polymers 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 229920001220 nitrocellulos Polymers 0.000 claims description 2
- 229920000058 polyacrylate Polymers 0.000 claims description 2
- 229920000728 polyester Polymers 0.000 claims description 2
- 108090000623 proteins and genes Proteins 0.000 claims description 2
- 102000004169 proteins and genes Human genes 0.000 claims description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims 2
- 235000013870 dimethyl polysiloxane Nutrition 0.000 claims 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 2
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 claims 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims 1
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 claims 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 claims 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims 1
- WOQDKFVDSKUVFC-UHFFFAOYSA-O CC(=C)C(=O)CCP(=O)=C(O)C[N+](C)(C)C Chemical compound CC(=C)C(=O)CCP(=O)=C(O)C[N+](C)(C)C WOQDKFVDSKUVFC-UHFFFAOYSA-O 0.000 claims 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims 1
- 229920000877 Melamine resin Polymers 0.000 claims 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims 1
- 239000004721 Polyphenylene oxide Substances 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- 125000005250 alkyl acrylate group Chemical group 0.000 claims 1
- 150000001350 alkyl halides Chemical class 0.000 claims 1
- 235000013877 carbamide Nutrition 0.000 claims 1
- WNPMPFBJTYCQEL-UHFFFAOYSA-N carbonic acid;ethyl carbamate Chemical compound OC(O)=O.CCOC(N)=O WNPMPFBJTYCQEL-UHFFFAOYSA-N 0.000 claims 1
- 239000001768 carboxy methyl cellulose Substances 0.000 claims 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 claims 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 claims 1
- 229940105329 carboxymethylcellulose Drugs 0.000 claims 1
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 claims 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 claims 1
- ZNAOFAIBVOMLPV-UHFFFAOYSA-N hexadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCOC(=O)C(C)=C ZNAOFAIBVOMLPV-UHFFFAOYSA-N 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- 239000011976 maleic acid Substances 0.000 claims 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims 1
- 150000002826 nitrites Chemical class 0.000 claims 1
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 claims 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims 1
- 229920000193 polymethacrylate Polymers 0.000 claims 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 claims 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 claims 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims 1
- 239000012815 thermoplastic material Substances 0.000 claims 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 1
- 150000003672 ureas Chemical class 0.000 claims 1
- 239000010410 layer Substances 0.000 description 275
- 239000003795 chemical substances by application Substances 0.000 description 54
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 51
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 42
- 239000013543 active substance Substances 0.000 description 36
- 239000000243 solution Substances 0.000 description 34
- 239000003999 initiator Substances 0.000 description 21
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 229960004592 isopropanol Drugs 0.000 description 17
- 239000013047 polymeric layer Substances 0.000 description 16
- 229910001220 stainless steel Inorganic materials 0.000 description 16
- 239000010935 stainless steel Substances 0.000 description 16
- 238000011068 loading method Methods 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 15
- 239000000126 substance Substances 0.000 description 15
- 239000003146 anticoagulant agent Substances 0.000 description 14
- 229940127219 anticoagulant drug Drugs 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- 239000004019 antithrombin Chemical class 0.000 description 11
- 229940079593 drug Drugs 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 10
- NOBYOEQUFMGXBP-UHFFFAOYSA-N (4-tert-butylcyclohexyl) (4-tert-butylcyclohexyl)oxycarbonyloxy carbonate Chemical compound C1CC(C(C)(C)C)CCC1OC(=O)OOC(=O)OC1CCC(C(C)(C)C)CC1 NOBYOEQUFMGXBP-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 238000006116 polymerization reaction Methods 0.000 description 9
- 238000003756 stirring Methods 0.000 description 8
- 210000001519 tissue Anatomy 0.000 description 8
- 229940044192 2-hydroxyethyl methacrylate Drugs 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- WQPDUTSPKFMPDP-OUMQNGNKSA-N hirudin Chemical compound C([C@@H](C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C=CC(OS(O)(=O)=O)=CC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(O)=O)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H]1NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@@H]2CSSC[C@@H](C(=O)N[C@@H](CCC(O)=O)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@H](C(=O)N[C@H](C(NCC(=O)N[C@@H](CCC(N)=O)C(=O)NCC(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)N2)=O)CSSC1)C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]1NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CO)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=2C=CC(O)=CC=2)NC(=O)[C@@H](NC(=O)[C@@H](N)C(C)C)C(C)C)[C@@H](C)O)CSSC1)C(C)C)[C@@H](C)O)[C@@H](C)O)C1=CC=CC=C1 WQPDUTSPKFMPDP-OUMQNGNKSA-N 0.000 description 7
- 239000003208 petroleum Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- OHCQJHSOBUTRHG-KGGHGJDLSA-N FORSKOLIN Chemical compound O=C([C@@]12O)C[C@](C)(C=C)O[C@]1(C)[C@@H](OC(=O)C)[C@@H](O)[C@@H]1[C@]2(C)[C@@H](O)CCC1(C)C OHCQJHSOBUTRHG-KGGHGJDLSA-N 0.000 description 6
- 229940122388 Thrombin inhibitor Drugs 0.000 description 6
- 230000000977 initiatory effect Effects 0.000 description 6
- FZWBNHMXJMCXLU-BLAUPYHCSA-N isomaltotriose 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](O)[C@@H](O)[C@@H](OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O)O1 FZWBNHMXJMCXLU-BLAUPYHCSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000003868 thrombin inhibitor Substances 0.000 description 6
- 239000004342 Benzoyl peroxide Substances 0.000 description 5
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 5
- 230000000702 anti-platelet effect Effects 0.000 description 5
- 235000019400 benzoyl peroxide Nutrition 0.000 description 5
- 239000003102 growth factor Substances 0.000 description 5
- 238000000386 microscopy Methods 0.000 description 5
- 239000012038 nucleophile Substances 0.000 description 5
- AVTLBBWTUPQRAY-UHFFFAOYSA-N 2-(2-cyanobutan-2-yldiazenyl)-2-methylbutanenitrile Chemical compound CCC(C)(C#N)N=NC(C)(CC)C#N AVTLBBWTUPQRAY-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 102000007625 Hirudins Human genes 0.000 description 4
- 108010007267 Hirudins Proteins 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 229960002086 dextran Drugs 0.000 description 4
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 4
- 229940006607 hirudin Drugs 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- 239000002504 physiological saline solution Substances 0.000 description 4
- 239000002464 receptor antagonist Substances 0.000 description 4
- 229940044551 receptor antagonist Drugs 0.000 description 4
- GQGRDYWMOPRROR-ZIFKCHSBSA-N (e)-7-[(1r,2r,3s,5s)-3-hydroxy-5-[(4-phenylphenyl)methoxy]-2-piperidin-1-ylcyclopentyl]hept-4-enoic acid Chemical compound O([C@H]1C[C@@H]([C@@H]([C@H]1CC\C=C\CCC(O)=O)N1CCCCC1)O)CC(C=C1)=CC=C1C1=CC=CC=C1 GQGRDYWMOPRROR-ZIFKCHSBSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- SUZLHDUTVMZSEV-UHFFFAOYSA-N Deoxycoleonol Natural products C12C(=O)CC(C)(C=C)OC2(C)C(OC(=O)C)C(O)C2C1(C)C(O)CCC2(C)C SUZLHDUTVMZSEV-UHFFFAOYSA-N 0.000 description 3
- 229920001499 Heparinoid Polymers 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 3
- 239000002260 anti-inflammatory agent Substances 0.000 description 3
- KXNPVXPOPUZYGB-XYVMCAHJSA-N argatroban Chemical compound OC(=O)[C@H]1C[C@H](C)CCN1C(=O)[C@H](CCCN=C(N)N)NS(=O)(=O)C1=CC=CC2=C1NC[C@H](C)C2 KXNPVXPOPUZYGB-XYVMCAHJSA-N 0.000 description 3
- 229960003856 argatroban Drugs 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 229960000686 benzalkonium chloride Drugs 0.000 description 3
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 3
- 239000012620 biological material Substances 0.000 description 3
- OHCQJHSOBUTRHG-UHFFFAOYSA-N colforsin Natural products OC12C(=O)CC(C)(C=C)OC1(C)C(OC(=O)C)C(O)C1C2(C)C(O)CCC1(C)C OHCQJHSOBUTRHG-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 231100000599 cytotoxic agent Toxicity 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- 239000000032 diagnostic agent Substances 0.000 description 3
- 229940039227 diagnostic agent Drugs 0.000 description 3
- 239000012975 dibutyltin dilaurate Substances 0.000 description 3
- 229960002768 dipyridamole Drugs 0.000 description 3
- IZEKFCXSFNUWAM-UHFFFAOYSA-N dipyridamole Chemical compound C=12N=C(N(CCO)CCO)N=C(N3CCCCC3)C2=NC(N(CCO)CCO)=NC=1N1CCCCC1 IZEKFCXSFNUWAM-UHFFFAOYSA-N 0.000 description 3
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 3
- 239000012039 electrophile Substances 0.000 description 3
- 229950003499 fibrin Drugs 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- ZFGMDIBRIDKWMY-PASTXAENSA-N heparin Chemical compound CC(O)=N[C@@H]1[C@@H](O)[C@H](O)[C@@H](COS(O)(=O)=O)O[C@@H]1O[C@@H]1[C@@H](C(O)=O)O[C@@H](O[C@H]2[C@@H]([C@@H](OS(O)(=O)=O)[C@@H](O[C@@H]3[C@@H](OC(O)[C@H](OS(O)(=O)=O)[C@H]3O)C(O)=O)O[C@@H]2O)CS(O)(=O)=O)[C@H](O)[C@H]1O ZFGMDIBRIDKWMY-PASTXAENSA-N 0.000 description 3
- 239000002554 heparinoid Substances 0.000 description 3
- 229940025770 heparinoids Drugs 0.000 description 3
- 229920002674 hyaluronan Polymers 0.000 description 3
- 229960003160 hyaluronic acid Drugs 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 238000012856 packing Methods 0.000 description 3
- 229920006254 polymer film Polymers 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 229950003937 tolonium Drugs 0.000 description 3
- HNONEKILPDHFOL-UHFFFAOYSA-M tolonium chloride Chemical compound [Cl-].C1=C(C)C(N)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 HNONEKILPDHFOL-UHFFFAOYSA-M 0.000 description 3
- 229950007952 vapiprost Drugs 0.000 description 3
- PJVWKTKQMONHTI-UHFFFAOYSA-N warfarin Chemical compound OC=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 PJVWKTKQMONHTI-UHFFFAOYSA-N 0.000 description 3
- 229960005080 warfarin Drugs 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- WEQJQNWXCSUVMA-NEPJUHHUSA-N (2s)-1-[(2r)-2-azaniumyl-3-phenylpropanoyl]pyrrolidine-2-carboxylate Chemical compound C([C@@H](N)C(=O)N1[C@@H](CCC1)C(O)=O)C1=CC=CC=C1 WEQJQNWXCSUVMA-NEPJUHHUSA-N 0.000 description 2
- XSHISXQEKIKSGC-UHFFFAOYSA-N 2-aminoethyl 2-methylprop-2-enoate;hydron;chloride Chemical compound Cl.CC(=C)C(=O)OCCN XSHISXQEKIKSGC-UHFFFAOYSA-N 0.000 description 2
- QLIBJPGWWSHWBF-UHFFFAOYSA-N 2-aminoethyl methacrylate Chemical compound CC(=C)C(=O)OCCN QLIBJPGWWSHWBF-UHFFFAOYSA-N 0.000 description 2
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 2
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 2
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 2
- 101710112752 Cytotoxin Proteins 0.000 description 2
- 102000003886 Glycoproteins Human genes 0.000 description 2
- 108090000288 Glycoproteins Proteins 0.000 description 2
- 229940123011 Growth factor receptor antagonist Drugs 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 229960001138 acetylsalicylic acid Drugs 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 description 2
- 230000001028 anti-proliverative effect Effects 0.000 description 2
- 229940030225 antihemorrhagics Drugs 0.000 description 2
- 239000003443 antiviral agent Substances 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 230000001588 bifunctional effect Effects 0.000 description 2
- 239000012867 bioactive agent Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000012505 colouration Methods 0.000 description 2
- 239000002619 cytotoxin Substances 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000003193 general anesthetic agent Substances 0.000 description 2
- 150000004676 glycans Chemical class 0.000 description 2
- 239000002874 hemostatic agent Substances 0.000 description 2
- 239000005556 hormone Substances 0.000 description 2
- 229940088597 hormone Drugs 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 230000001788 irregular Effects 0.000 description 2
- 229940127215 low-molecular weight heparin Drugs 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 108010088904 phenylalanylproline Proteins 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920001485 poly(butyl acrylate) polymer Polymers 0.000 description 2
- 239000002685 polymerization catalyst Substances 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 229920001282 polysaccharide Polymers 0.000 description 2
- 239000005017 polysaccharide Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 230000000069 prophylactic effect Effects 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 229920005604 random copolymer Polymers 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000013268 sustained release Methods 0.000 description 2
- 239000012730 sustained-release form Substances 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- 229920001897 terpolymer Polymers 0.000 description 2
- 210000005167 vascular cell Anatomy 0.000 description 2
- 239000003071 vasodilator agent Substances 0.000 description 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
- OQANPHBRHBJGNZ-FYJGNVAPSA-N (3e)-6-oxo-3-[[4-(pyridin-2-ylsulfamoyl)phenyl]hydrazinylidene]cyclohexa-1,4-diene-1-carboxylic acid Chemical compound C1=CC(=O)C(C(=O)O)=C\C1=N\NC1=CC=C(S(=O)(=O)NC=2N=CC=CC=2)C=C1 OQANPHBRHBJGNZ-FYJGNVAPSA-N 0.000 description 1
- PUDHBTGHUJUUFI-SCTWWAJVSA-N (4r,7s,10s,13r,16s,19r)-10-(4-aminobutyl)-n-[(2s,3r)-1-amino-3-hydroxy-1-oxobutan-2-yl]-19-[[(2r)-2-amino-3-naphthalen-2-ylpropanoyl]amino]-16-[(4-hydroxyphenyl)methyl]-13-(1h-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-7-propan-2-yl-1,2-dithia-5,8,11,14,17-p Chemical compound C([C@H]1C(=O)N[C@H](CC=2C3=CC=CC=C3NC=2)C(=O)N[C@@H](CCCCN)C(=O)N[C@H](C(N[C@@H](CSSC[C@@H](C(=O)N1)NC(=O)[C@H](N)CC=1C=C2C=CC=CC2=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(N)=O)=O)C(C)C)C1=CC=C(O)C=C1 PUDHBTGHUJUUFI-SCTWWAJVSA-N 0.000 description 1
- ZKMNUMMKYBVTFN-HNNXBMFYSA-N (S)-ropivacaine Chemical compound CCCN1CCCC[C@H]1C(=O)NC1=C(C)C=CC=C1C ZKMNUMMKYBVTFN-HNNXBMFYSA-N 0.000 description 1
- BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-UHFFFAOYSA-N 0.000 description 1
- SUNMBRGCANLOEG-UHFFFAOYSA-N 1,3-dichloroacetone Chemical compound ClCC(=O)CCl SUNMBRGCANLOEG-UHFFFAOYSA-N 0.000 description 1
- LEBVLXFERQHONN-UHFFFAOYSA-N 1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide Chemical compound CCCCN1CCCCC1C(=O)NC1=C(C)C=CC=C1C LEBVLXFERQHONN-UHFFFAOYSA-N 0.000 description 1
- UDJZTGMLYITLIQ-UHFFFAOYSA-N 1-ethenylpyrrolidine Chemical compound C=CN1CCCC1 UDJZTGMLYITLIQ-UHFFFAOYSA-N 0.000 description 1
- VNDNKFJKUBLYQB-UHFFFAOYSA-N 2-(4-amino-6-chloro-5-oxohexyl)guanidine Chemical compound ClCC(=O)C(N)CCCN=C(N)N VNDNKFJKUBLYQB-UHFFFAOYSA-N 0.000 description 1
- 102400000068 Angiostatin Human genes 0.000 description 1
- 108010079709 Angiostatins Proteins 0.000 description 1
- IYMAXBFPHPZYIK-BQBZGAKWSA-N Arg-Gly-Asp Chemical compound NC(N)=NCCC[C@H](N)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(O)=O IYMAXBFPHPZYIK-BQBZGAKWSA-N 0.000 description 1
- VOVIALXJUBGFJZ-KWVAZRHASA-N Budesonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(CCC)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O VOVIALXJUBGFJZ-KWVAZRHASA-N 0.000 description 1
- OXJGJKIURHREKH-UHFFFAOYSA-O CC(=C)C(=O)OCCP(=O)=C(O)C[N+](C)(C)C Chemical compound CC(=C)C(=O)OCCP(=O)=C(O)C[N+](C)(C)C OXJGJKIURHREKH-UHFFFAOYSA-O 0.000 description 1
- OMFXVFTZEKFJBZ-UHFFFAOYSA-N Corticosterone Natural products O=C1CCC2(C)C3C(O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 OMFXVFTZEKFJBZ-UHFFFAOYSA-N 0.000 description 1
- 102000004127 Cytokines Human genes 0.000 description 1
- 108090000695 Cytokines Proteins 0.000 description 1
- 102400001047 Endostatin Human genes 0.000 description 1
- 108010079505 Endostatins Proteins 0.000 description 1
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 1
- 241000282414 Homo sapiens Species 0.000 description 1
- UETNIIAIRMUTSM-UHFFFAOYSA-N Jacareubin Natural products CC1(C)OC2=CC3Oc4c(O)c(O)ccc4C(=O)C3C(=C2C=C1)O UETNIIAIRMUTSM-UHFFFAOYSA-N 0.000 description 1
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 1
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- NTUPOKHATNSWCY-JYJNAYRXSA-N Phe-Pro-Arg Chemical compound C([C@H](N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCN=C(N)N)C(O)=O)C1=CC=CC=C1 NTUPOKHATNSWCY-JYJNAYRXSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 108010039918 Polylysine Proteins 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 229920002396 Polyurea Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 1
- 102000003990 Urokinase-type plasminogen activator Human genes 0.000 description 1
- 108090000435 Urokinase-type plasminogen activator Proteins 0.000 description 1
- JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 description 1
- 206010052428 Wound Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000012644 addition polymerization Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229920006125 amorphous polymer Polymers 0.000 description 1
- 229940124326 anaesthetic agent Drugs 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 208000007502 anemia Diseases 0.000 description 1
- 229940125709 anorectic agent Drugs 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 230000003556 anti-epileptic effect Effects 0.000 description 1
- 230000001387 anti-histamine Effects 0.000 description 1
- 229940124599 anti-inflammatory drug Drugs 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000118 anti-neoplastic effect Effects 0.000 description 1
- 230000000561 anti-psychotic effect Effects 0.000 description 1
- 230000002965 anti-thrombogenic effect Effects 0.000 description 1
- 239000000924 antiasthmatic agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000003529 anticholesteremic agent Substances 0.000 description 1
- 229940127226 anticholesterol agent Drugs 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 239000003472 antidiabetic agent Substances 0.000 description 1
- 229940125708 antidiabetic agent Drugs 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 229940121357 antivirals Drugs 0.000 description 1
- 239000002830 appetite depressant Substances 0.000 description 1
- 108010072041 arginyl-glycyl-aspartic acid Proteins 0.000 description 1
- FZCSTZYAHCUGEM-UHFFFAOYSA-N aspergillomarasmine B Natural products OC(=O)CNC(C(O)=O)CNC(C(O)=O)CC(O)=O FZCSTZYAHCUGEM-UHFFFAOYSA-N 0.000 description 1
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- 239000002876 beta blocker Substances 0.000 description 1
- 229940097320 beta blocking agent Drugs 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229960004436 budesonide Drugs 0.000 description 1
- 229960003150 bupivacaine Drugs 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000002327 cardiovascular agent Substances 0.000 description 1
- 229940125692 cardiovascular agent Drugs 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000003874 central nervous system depressant Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 125000003636 chemical group Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 1
- 229960004316 cisplatin Drugs 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- OMFXVFTZEKFJBZ-HJTSIMOOSA-N corticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OMFXVFTZEKFJBZ-HJTSIMOOSA-N 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 239000002254 cytotoxic agent Substances 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- ISAOCJYIOMOJEB-UHFFFAOYSA-N desyl alcohol Natural products C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 1
- 229960003957 dexamethasone Drugs 0.000 description 1
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 1
- 238000004455 differential thermal analysis Methods 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000000890 drug combination Substances 0.000 description 1
- 230000009881 electrostatic interaction Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 229930013356 epothilone Natural products 0.000 description 1
- HESCAJZNRMSMJG-KKQRBIROSA-N epothilone A Chemical class C/C([C@@H]1C[C@@H]2O[C@@H]2CCC[C@@H]([C@@H]([C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O1)O)C)=C\C1=CSC(C)=N1 HESCAJZNRMSMJG-KKQRBIROSA-N 0.000 description 1
- 229940011871 estrogen Drugs 0.000 description 1
- 239000000262 estrogen Substances 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000003527 fibrinolytic agent Substances 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229960002949 fluorouracil Drugs 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 210000005224 forefinger Anatomy 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 238000001415 gene therapy Methods 0.000 description 1
- 125000005639 glycero group Chemical group 0.000 description 1
- 239000003966 growth inhibitor Substances 0.000 description 1
- 239000007952 growth promoter Substances 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 239000002628 heparin derivative Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000003326 hypnotic agent Substances 0.000 description 1
- 239000012216 imaging agent Substances 0.000 description 1
- 230000005847 immunogenicity Effects 0.000 description 1
- 239000002955 immunomodulating agent Substances 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 108010021336 lanreotide Proteins 0.000 description 1
- 229960002437 lanreotide Drugs 0.000 description 1
- 239000012633 leachable Substances 0.000 description 1
- 229960004194 lidocaine Drugs 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- KBOPZPXVLCULAV-UHFFFAOYSA-N mesalamine Chemical compound NC1=CC=C(O)C(C(O)=O)=C1 KBOPZPXVLCULAV-UHFFFAOYSA-N 0.000 description 1
- 229960004963 mesalazine Drugs 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000003604 miotic agent Substances 0.000 description 1
- 239000003149 muscarinic antagonist Substances 0.000 description 1
- 229960002715 nicotine Drugs 0.000 description 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- 239000002840 nitric oxide donor Substances 0.000 description 1
- 230000001453 nonthrombogenic effect Effects 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 238000002103 osmometry Methods 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000000106 platelet aggregation inhibitor Substances 0.000 description 1
- 229920000141 poly(maleic anhydride) Polymers 0.000 description 1
- 229920000580 poly(melamine) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 238000012643 polycondensation polymerization Methods 0.000 description 1
- 229920000120 polyethyl acrylate Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920000656 polylysine Polymers 0.000 description 1
- 229920001444 polymaleic acid Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 229960005205 prednisolone Drugs 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
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002089 prostaglandin antagonist Substances 0.000 description 1
- 239000003196 psychodysleptic agent Substances 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000012217 radiopharmaceutical Substances 0.000 description 1
- 229940121896 radiopharmaceutical Drugs 0.000 description 1
- 230000002799 radiopharmaceutical effect Effects 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- 229960001549 ropivacaine Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 210000000329 smooth muscle myocyte Anatomy 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229960001940 sulfasalazine Drugs 0.000 description 1
- NCEXYHBECQHGNR-UHFFFAOYSA-N sulfasalazine Natural products C1=C(O)C(C(=O)O)=CC(N=NC=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 229940126585 therapeutic drug Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 210000003813 thumb Anatomy 0.000 description 1
- 239000003803 thymidine kinase inhibitor Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 108091006106 transcriptional activators Proteins 0.000 description 1
- 108091006107 transcriptional repressors Proteins 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 229960005356 urokinase Drugs 0.000 description 1
- 239000002550 vasoactive agent Substances 0.000 description 1
- 230000002227 vasoactive effect Effects 0.000 description 1
- 239000005526 vasoconstrictor agent Substances 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 229960003048 vinblastine Drugs 0.000 description 1
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
- 229960004528 vincristine Drugs 0.000 description 1
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 238000003260 vortexing Methods 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
- 239000003357 wound healing promoting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1804—C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
- A61L31/04—Macromolecular materials
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
- A61L31/08—Materials for coatings
- A61L31/10—Macromolecular materials
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
- A61L31/14—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
- A61L31/16—Biologically active materials, e.g. therapeutic substances
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
- A61L2300/416—Anti-neoplastic or anti-proliferative or anti-restenosis or anti-angiogenic agents, e.g. paclitaxel, sirolimus
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/60—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a special physical form
- A61L2300/606—Coatings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/60—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a special physical form
- A61L2300/606—Coatings
- A61L2300/608—Coatings having two or more layers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2420/00—Materials or methods for coatings medical devices
- A61L2420/02—Methods for coating medical devices
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1812—C12-(meth)acrylate, e.g. lauryl (meth)acrylate
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/24—Structurally defined web or sheet [e.g., overall dimension, etc.]
- Y10T428/24942—Structurally defined web or sheet [e.g., overall dimension, etc.] including components having same physical characteristic in differing degree
- Y10T428/2495—Thickness [relative or absolute]
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31855—Of addition polymer from unsaturated monomers
- Y10T428/31909—Next to second addition polymer from unsaturated monomers
- Y10T428/31928—Ester, halide or nitrile of addition polymer
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Surgery (AREA)
- Vascular Medicine (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Biomedical Technology (AREA)
- Molecular Biology (AREA)
- Materials For Medical Uses (AREA)
- Prostheses (AREA)
- Paints Or Removers (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US45133303P | 2003-02-28 | 2003-02-28 | |
| US60/451,333 | 2003-02-28 | ||
| PCT/IB2004/000534 WO2004075943A1 (en) | 2003-02-28 | 2004-03-01 | Polymeric network system for medical devices and methods of use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2519503A1 CA2519503A1 (en) | 2004-09-10 |
| CA2519503C true CA2519503C (en) | 2015-04-28 |
Family
ID=32927706
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2519503A Expired - Lifetime CA2519503C (en) | 2003-02-28 | 2004-03-01 | Drug delivery from a polymer coating on a medical device |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US7655038B2 (enExample) |
| EP (2) | EP1603603B1 (enExample) |
| JP (1) | JP4791349B2 (enExample) |
| AU (1) | AU2004216404C1 (enExample) |
| CA (1) | CA2519503C (enExample) |
| DK (1) | DK1603603T3 (enExample) |
| ES (1) | ES2531326T3 (enExample) |
| HK (1) | HK1215199A1 (enExample) |
| PL (1) | PL1603603T3 (enExample) |
| PT (1) | PT1603603E (enExample) |
| WO (1) | WO2004075943A1 (enExample) |
Families Citing this family (93)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20020188037A1 (en) * | 1999-04-15 | 2002-12-12 | Chudzik Stephen J. | Method and system for providing bioactive agent release coating |
| ATE219693T1 (de) | 1998-04-27 | 2002-07-15 | Surmodics Inc | Bioaktive wirkstoffe freisetzende beschichtungen |
| US7097850B2 (en) | 2002-06-18 | 2006-08-29 | Surmodics, Inc. | Bioactive agent release coating and controlled humidity method |
| US7655038B2 (en) | 2003-02-28 | 2010-02-02 | Biointeractions Ltd. | Polymeric network system for medical devices and methods of use |
| US20040111144A1 (en) * | 2002-12-06 | 2004-06-10 | Lawin Laurie R. | Barriers for polymeric coatings |
| US7776926B1 (en) | 2002-12-11 | 2010-08-17 | Advanced Cardiovascular Systems, Inc. | Biocompatible coating for implantable medical devices |
| US7758880B2 (en) | 2002-12-11 | 2010-07-20 | Advanced Cardiovascular Systems, Inc. | Biocompatible polyacrylate compositions for medical applications |
| GB2422335B8 (en) * | 2003-09-19 | 2009-04-01 | Sumitomo Bakelite Co | Chip for detection or analysis of biologically active substance |
| CA2541850A1 (en) * | 2003-10-15 | 2005-04-28 | Tyco Healthcare Group Lp | Method of joining materials |
| WO2005097223A1 (en) * | 2004-03-26 | 2005-10-20 | Surmodics, Inc. | Composition and method for preparing biocompatible surfaces |
| EP1735024A1 (en) | 2004-03-26 | 2006-12-27 | SurModics, Inc. | Process and systems for biocompatible surfaces |
| JP2007532187A (ja) | 2004-04-06 | 2007-11-15 | サーモディクス，インコーポレイティド | 生物活性物質のためのコーティング組成物 |
| WO2005115490A2 (en) * | 2004-05-25 | 2005-12-08 | Surmodics, Inc. | Natural biodegradable polysaccharide coatings for meical articles |
| US20060088571A1 (en) * | 2004-10-21 | 2006-04-27 | Medtronic Vascular, Inc. | Biocompatible and hemocompatible polymer compositions |
| US7919110B2 (en) * | 2005-01-25 | 2011-04-05 | Boston Scientific Scimed, Inc. | Medical device drug release regions containing non-covalently bound polymers |
| US20060171980A1 (en) * | 2005-02-01 | 2006-08-03 | Helmus Michael N | Implantable or insertable medical devices having optimal surface energy |
| US8075906B2 (en) * | 2005-02-01 | 2011-12-13 | Boston Scientific Scimed, Inc. | Medical devices having polymeric regions with copolymers containing hydrocarbon and heteroatom-containing monomeric species |
| US7517914B2 (en) * | 2005-04-04 | 2009-04-14 | Boston Scientificscimed, Inc. | Controlled degradation materials for therapeutic agent delivery |
| US7591841B2 (en) * | 2005-12-16 | 2009-09-22 | Advanced Cardiovascular Systems, Inc. | Implantable devices for accelerated healing |
| US20070155907A1 (en) * | 2005-12-30 | 2007-07-05 | Zhao Jonathon Z | Biologically active block copolymers |
| US11039942B2 (en) * | 2006-06-13 | 2021-06-22 | Sino Medical Sciences Technology Inc. | Drug eluting stent and method of use of the same for enabling restoration of functional endothelial cell layers |
| US10188826B2 (en) * | 2006-09-29 | 2019-01-29 | Covidien Lp | Catheters including antimicrobial sleeve and methods of making catheters |
| US9474833B2 (en) * | 2006-12-18 | 2016-10-25 | Cook Medical Technologies Llc | Stent graft with releasable therapeutic agent and soluble coating |
| WO2008131360A1 (en) * | 2007-04-20 | 2008-10-30 | Becton, Dickinson And Company | Hydrogel compositions |
| US8133553B2 (en) | 2007-06-18 | 2012-03-13 | Zimmer, Inc. | Process for forming a ceramic layer |
| US8309521B2 (en) | 2007-06-19 | 2012-11-13 | Zimmer, Inc. | Spacer with a coating thereon for use with an implant device |
| US8608049B2 (en) | 2007-10-10 | 2013-12-17 | Zimmer, Inc. | Method for bonding a tantalum structure to a cobalt-alloy substrate |
| US8128706B2 (en) * | 2008-01-09 | 2012-03-06 | Innovative Health Technologies, Llc | Implant pellets and methods for performing bone augmentation and preservation |
| DE102008006654A1 (de) * | 2008-01-30 | 2009-08-06 | Biotronik Vi Patent Ag | Implantat mit einem Grundkörper aus einer biokorrodierbaren Legierung |
| JP2011512215A (ja) * | 2008-02-21 | 2011-04-21 | エグザカトゥ | 活性成分又は薬剤用、特に水溶性のもの用の保護／保持層を備える植込み型医用装置 |
| US8034396B2 (en) * | 2008-04-01 | 2011-10-11 | Tyco Healthcare Group Lp | Bioadhesive composition formed using click chemistry |
| EP2268332B1 (de) * | 2008-04-09 | 2019-01-16 | Aachen Scientific International PTE. LTD. | Verfahren zur erzeugung einer bioaktiven oberfläche auf einer endoprothese oder auf dem ballon eines ballonkatheters |
| US20090264478A1 (en) * | 2008-04-18 | 2009-10-22 | Warsaw Orthopedic, Inc. | Sulfasalazine formulations in a biodegradable polymer carrier |
| GB0816783D0 (en) * | 2008-09-15 | 2008-10-22 | Carmeda Ab | Immobilised biological entities |
| US8226603B2 (en) | 2008-09-25 | 2012-07-24 | Abbott Cardiovascular Systems Inc. | Expandable member having a covering formed of a fibrous matrix for intraluminal drug delivery |
| US8049061B2 (en) | 2008-09-25 | 2011-11-01 | Abbott Cardiovascular Systems, Inc. | Expandable member formed of a fibrous matrix having hydrogel polymer for intraluminal drug delivery |
| US8076529B2 (en) | 2008-09-26 | 2011-12-13 | Abbott Cardiovascular Systems, Inc. | Expandable member formed of a fibrous matrix for intraluminal drug delivery |
| US9523159B2 (en) | 2009-02-21 | 2016-12-20 | Covidien Lp | Crosslinked fibers and method of making same using UV radiation |
| US8512728B2 (en) | 2009-02-21 | 2013-08-20 | Sofradim Production | Method of forming a medical device on biological tissue |
| AU2010215194A1 (en) | 2009-02-21 | 2011-10-13 | Sofradim Production | Apparatus and method of reacting polymers passing through metal ion chelated resin matrix to produce injectable medical devices |
| US8535477B2 (en) | 2009-02-21 | 2013-09-17 | Sofradim Production | Medical devices incorporating functional adhesives |
| US8663689B2 (en) * | 2009-02-21 | 2014-03-04 | Sofradim Production | Functionalized adhesive medical gel |
| WO2010095049A1 (en) | 2009-02-21 | 2010-08-26 | Sofradim Production | Crosslinked fibers and method of making same by extrusion |
| AU2010215192B2 (en) | 2009-02-21 | 2015-04-30 | Sofradim Production | Amphiphilic compounds and self-assembling compositions made therefrom |
| WO2010095053A2 (en) | 2009-02-21 | 2010-08-26 | Sofradim Production | Apparatus and method of reaching polymers by exposure to uv radiation to produce injectable medical devices |
| US9273191B2 (en) | 2009-02-21 | 2016-03-01 | Sofradim Production | Medical devices with an activated coating |
| US8877170B2 (en) * | 2009-02-21 | 2014-11-04 | Sofradim Production | Medical device with inflammatory response-reducing coating |
| EP2398524B1 (en) | 2009-02-21 | 2017-07-12 | Covidien LP | Medical devices having activated surfaces |
| US8968733B2 (en) * | 2009-02-21 | 2015-03-03 | Sofradim Production | Functionalized surgical adhesives |
| WO2010096649A1 (en) | 2009-02-21 | 2010-08-26 | Tyco Healthcare Group Lp | Medical devices having activated surfaces |
| EP2398519A2 (en) * | 2009-02-21 | 2011-12-28 | Sofradim Production | Compounds and medical devices activated with solvophobic linkers |
| CN102933658A (zh) | 2009-12-18 | 2013-02-13 | 界面生物公司 | 从自组装涂层局部递送药物 |
| EP2338534A2 (de) * | 2009-12-21 | 2011-06-29 | Biotronik VI Patent AG | Medizinisches Implantat, Beschichtungsverfahren sowie Implantationsverfahren |
| GB201004101D0 (en) | 2010-03-12 | 2010-04-28 | Carmeda Ab | Immobilised biological entities |
| WO2011119536A1 (en) | 2010-03-22 | 2011-09-29 | Abbott Cardiovascular Systems Inc. | Stent delivery system having a fibrous matrix covering with improved stent retention |
| CA2794336A1 (en) | 2010-03-25 | 2011-09-29 | Sofradim Production | Surgical fasteners and methods for sealing wounds |
| EP2550031B1 (en) | 2010-03-25 | 2015-08-19 | Sofradim Production | Medical devices incorporating functional adhesives |
| EP2549933A4 (en) * | 2010-03-25 | 2015-10-14 | Covidien Lp | CHEMICAL KNOTS FOR SEAMS |
| EP3195858B1 (en) | 2010-04-03 | 2019-08-07 | Praful Doshi | Medical devices including medicaments and methods of making and using same |
| US10413506B2 (en) | 2010-04-03 | 2019-09-17 | Praful Doshi | Medical devices including medicaments and methods of making and using same including enhancing comfort, enhancing drug penetration, and treatment of myopia |
| EP2588525A4 (en) | 2010-06-29 | 2015-06-10 | Covidien Lp | MICROWAVE POWERED REACTOR AND IN SITU IMPLANT TRAINING METHOD |
| US8865857B2 (en) | 2010-07-01 | 2014-10-21 | Sofradim Production | Medical device with predefined activated cellular integration |
| AU2011284449B2 (en) | 2010-07-27 | 2015-07-23 | Sofradim Production | Polymeric fibers having tissue reactive members |
| TWI836373B (zh) | 2010-07-30 | 2024-03-21 | 瑞士商愛爾康公司 | 水合隱形鏡片 |
| WO2012153396A1 (ja) | 2011-05-10 | 2012-11-15 | 伊藤忠ケミカルフロンティア株式会社 | 非水性貼付剤 |
| US11786455B2 (en) | 2011-05-10 | 2023-10-17 | Itochu Chemical Frontier Corporation | Non-aqueous patch |
| ES3034911T3 (en) | 2011-05-10 | 2025-08-26 | Itochu Chemical Frontier Corp | Non-aqueous patch |
| JP6021269B2 (ja) | 2011-09-27 | 2016-11-09 | 伊藤忠ケミカルフロンティア株式会社 | 非水性貼付剤 |
| HUE029018T2 (en) | 2011-10-12 | 2017-02-28 | Novartis Ag | A method for producing UV absorbing contact lenses by coating |
| KR101201984B1 (ko) * | 2012-02-28 | 2012-11-15 | 주식회사 제네웰 | 창상 봉합용 조직접착제 및 그 제조방법 |
| RU2611038C2 (ru) * | 2012-03-27 | 2017-02-20 | Ф.Хоффманн-Ля Рош Аг | Улучшенная спейсерная мембрана для ферментного датчика in vivo |
| HUE031702T2 (en) | 2012-12-17 | 2017-07-28 | Novartis Ag | A method for producing improved UV absorbing ophthalmic lenses |
| US10206945B2 (en) * | 2013-04-26 | 2019-02-19 | Biointeractions Ltd. | Bioactive coatings |
| USRE49528E1 (en) * | 2013-04-26 | 2023-05-16 | Biointeractions Ltd. | Bioactive coatings |
| US9775928B2 (en) | 2013-06-18 | 2017-10-03 | Covidien Lp | Adhesive barbed filament |
| US9708087B2 (en) | 2013-12-17 | 2017-07-18 | Novartis Ag | Silicone hydrogel lens with a crosslinked hydrophilic coating |
| JP2016005533A (ja) * | 2014-05-30 | 2016-01-14 | 株式会社日本ステントテクノロジー | ステント |
| US20160015852A1 (en) * | 2014-07-15 | 2016-01-21 | Industrial Technology Research Institute | Composite material |
| SG10201901379TA (en) | 2014-08-26 | 2019-03-28 | Novartis Ag | Method for applying stable coating on silicone hydrogel contact lenses |
| CN104610516B (zh) * | 2015-01-12 | 2018-05-18 | 西北大学 | 含磷酰胆碱和聚乙二醇的功能聚合物及其抗污涂层的构建方法 |
| US9763892B2 (en) | 2015-06-01 | 2017-09-19 | Autotelic Llc | Immediate release phospholipid-coated therapeutic agent nanoparticles and related methods |
| JP6805488B2 (ja) | 2015-12-02 | 2020-12-23 | 国立大学法人山形大学 | 医療用具用重合体用単量体組成物、及び、医療用具用重合体 |
| SG11201803726VA (en) | 2015-12-15 | 2018-06-28 | Novartis Ag | Method for applying stable coating on silicone hydrogel contact lenses |
| WO2018024560A1 (en) * | 2016-08-03 | 2018-02-08 | Basf Se | New bio-recognition elements |
| CN111386478B (zh) | 2017-12-13 | 2023-11-14 | 爱尔康公司 | 周抛和月抛水梯度接触镜片 |
| CN112638436A (zh) | 2018-05-22 | 2021-04-09 | 界面生物公司 | 用于将药物递送至血管壁的组合物和方法 |
| CN109096431B (zh) * | 2018-08-21 | 2020-11-27 | 湖南工业大学 | 一种纳米发电机与自驱动传感器用聚丙烯酸丁酯-聚甲基丙烯酸丁酯共聚物及其制备方法 |
| WO2020144953A1 (ja) * | 2019-01-09 | 2020-07-16 | 株式会社日本触媒 | 防汚剤、防汚塗膜及び防汚塗膜付き基材 |
| JP2022528428A (ja) * | 2019-03-19 | 2022-06-10 | ジェイメドテック・コーティング・テクノロジーズ・プライベイト・リミテッド | 共有結合したヘパリン・コーティングを備える医療デバイス |
| AU2020302924A1 (en) | 2019-06-27 | 2022-02-17 | Layerbio, Inc. | Ocular device delivery methods and systems |
| CN113072669B (zh) * | 2020-01-03 | 2022-02-18 | 万华化学集团股份有限公司 | 核-壳结构的丙烯酸酯类可溶胀流变改性剂及其制备方法 |
| CN117159811A (zh) * | 2022-01-30 | 2023-12-05 | 苏州浩微生物医疗科技有限公司 | 一种表面处理组合物、医疗器械及其制备方法 |
| CN115970070B (zh) * | 2022-12-26 | 2023-08-18 | 上海发微医用材料有限公司 | 含亲水聚合物的涂层体系及双层涂层体系、亲水涂层和应用 |
Family Cites Families (63)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2353A (en) * | 1841-11-12 | i s p e t t i t s m i t h | ||
| US150549A (en) * | 1874-05-05 | e wing | ||
| US1937475A (en) * | 1930-09-24 | 1933-11-28 | Peter S Legge | Abrading apparatus |
| US6387379B1 (en) * | 1987-04-10 | 2002-05-14 | University Of Florida | Biofunctional surface modified ocular implants, surgical instruments, medical devices, prostheses, contact lenses and the like |
| CA2027921C (en) * | 1989-10-19 | 1997-12-09 | Nobuo Nakabayashi | Bone cement composition, cured product thereof, implant material and process for the preparation of the same |
| JP2751938B2 (ja) * | 1989-10-19 | 1998-05-18 | 宣男 中林 | 骨セメント組成物および硬化体 |
| US5843089A (en) * | 1990-12-28 | 1998-12-01 | Boston Scientific Corporation | Stent lining |
| EP0623150A4 (en) | 1992-11-19 | 1999-08-25 | Univ Case Western Reserve | Nonthrombogenic implant surfaces. |
| EP0689465A1 (en) * | 1993-03-18 | 1996-01-03 | Cedars-Sinai Medical Center | Drug incorporating and releasing polymeric coating for bioprosthesis |
| US5464650A (en) * | 1993-04-26 | 1995-11-07 | Medtronic, Inc. | Intravascular stent and method |
| US5637113A (en) * | 1994-12-13 | 1997-06-10 | Advanced Cardiovascular Systems, Inc. | Polymer film for wrapping a stent structure |
| US6231600B1 (en) * | 1995-02-22 | 2001-05-15 | Scimed Life Systems, Inc. | Stents with hybrid coating for medical devices |
| US5607475A (en) * | 1995-08-22 | 1997-03-04 | Medtronic, Inc. | Biocompatible medical article and method |
| GB9608882D0 (en) | 1996-04-30 | 1996-07-03 | Luthra Ajay K | Non-thrombogenic and anti-thrombogenic polymers |
| US5980972A (en) | 1996-12-20 | 1999-11-09 | Schneider (Usa) Inc | Method of applying drug-release coatings |
| US6273913B1 (en) | 1997-04-18 | 2001-08-14 | Cordis Corporation | Modified stent useful for delivery of drugs along stent strut |
| ES2353840T3 (es) | 1997-04-21 | 2011-03-07 | California Institute Of Technology | Recubrimientos tisulares poliméricos multifuncionales. |
| GB9714650D0 (en) * | 1997-07-11 | 1997-09-17 | Strakan Ltd | Block copolymer |
| IL122153A (en) | 1997-11-10 | 2005-03-20 | Alomone Labs Ltd | Biocompatible polymeric coating material |
| US6224625B1 (en) * | 1997-10-27 | 2001-05-01 | Iowa-India Investments Company Limited | Low profile highly expandable stent |
| US6221425B1 (en) | 1998-01-30 | 2001-04-24 | Advanced Cardiovascular Systems, Inc. | Lubricious hydrophilic coating for an intracorporeal medical device |
| US6007833A (en) | 1998-03-19 | 1999-12-28 | Surmodics, Inc. | Crosslinkable macromers bearing initiator groups |
| ATE219693T1 (de) * | 1998-04-27 | 2002-07-15 | Surmodics Inc | Bioaktive wirkstoffe freisetzende beschichtungen |
| FR2785812B1 (fr) * | 1998-11-16 | 2002-11-29 | Commissariat Energie Atomique | Protheses bioactives, notamment a proprietes immunosuppressives, antistenose et antithrombose, et leur fabrication |
| US6734256B1 (en) * | 1998-12-29 | 2004-05-11 | 3M Innovative Properties Company | Block copolymer hot-melt processable adhesives, methods of their preparation, and articles therefrom |
| WO2000041738A1 (en) | 1999-01-12 | 2000-07-20 | Quanam Medical Corporation | Polymer compositions for intraluminal stent |
| JP4991030B2 (ja) * | 1999-01-12 | 2012-08-01 | ボストン サイエンティフィック サイムド，インコーポレイテッド | 腔内ステント用の重合体組成物 |
| US6530950B1 (en) * | 1999-01-12 | 2003-03-11 | Quanam Medical Corporation | Intraluminal stent having coaxial polymer member |
| AU775875B2 (en) * | 1999-01-12 | 2004-08-19 | Quanam Medical Corporation | Composition and methods for administration of water-insoluble paclitaxel derivatives |
| US6340465B1 (en) | 1999-04-12 | 2002-01-22 | Edwards Lifesciences Corp. | Lubricious coatings for medical devices |
| GB2349644A (en) | 1999-05-01 | 2000-11-08 | Biointeractions Ltd | Infection resistant polymers, methods for their preparation, and their uses |
| US6287379B1 (en) * | 1999-06-10 | 2001-09-11 | Jack Khalifeh | Apparatus and method for disposing rubber waste material during the manufacturing of products which are heated in a rotary kiln |
| US6258121B1 (en) | 1999-07-02 | 2001-07-10 | Scimed Life Systems, Inc. | Stent coating |
| US6503556B2 (en) * | 2000-12-28 | 2003-01-07 | Advanced Cardiovascular Systems, Inc. | Methods of forming a coating for a prosthesis |
| US6713119B2 (en) | 1999-09-03 | 2004-03-30 | Advanced Cardiovascular Systems, Inc. | Biocompatible coating for a prosthesis and a method of forming the same |
| US6251136B1 (en) * | 1999-12-08 | 2001-06-26 | Advanced Cardiovascular Systems, Inc. | Method of layering a three-coated stent using pharmacological and polymeric agents |
| WO2001068722A1 (en) | 2000-03-13 | 2001-09-20 | Biocure, Inc. | Hydrogel biomedical articles |
| US6776796B2 (en) | 2000-05-12 | 2004-08-17 | Cordis Corportation | Antiinflammatory drug and delivery device |
| US7682648B1 (en) | 2000-05-31 | 2010-03-23 | Advanced Cardiovascular Systems, Inc. | Methods for forming polymeric coatings on stents |
| US6673385B1 (en) * | 2000-05-31 | 2004-01-06 | Advanced Cardiovascular Systems, Inc. | Methods for polymeric coatings stents |
| JP5100951B2 (ja) * | 2000-09-29 | 2012-12-19 | コーディス・コーポレイション | 被覆医用器具 |
| US6545097B2 (en) * | 2000-12-12 | 2003-04-08 | Scimed Life Systems, Inc. | Drug delivery compositions and medical devices containing block copolymer |
| DE10114247A1 (de) * | 2001-03-22 | 2002-10-10 | Heraeus Kulzer Gmbh & Co Kg | Antibiotikum-/Antibiotika-Polymer-Kombination |
| US8101196B2 (en) * | 2001-06-26 | 2012-01-24 | Biointeractions, Ltd. | Polysaccharide biomaterials and methods of use thereof |
| GB0122393D0 (en) | 2001-09-17 | 2001-11-07 | Polybiomed Ltd | Treating metal surfaces to enhance bio-compatibility |
| US7655038B2 (en) | 2003-02-28 | 2010-02-02 | Biointeractions Ltd. | Polymeric network system for medical devices and methods of use |
| US7491233B1 (en) * | 2002-07-19 | 2009-02-17 | Advanced Cardiovascular Systems Inc. | Purified polymers for coatings of implantable medical devices |
| US6806320B2 (en) * | 2002-11-15 | 2004-10-19 | 3M Innovative Properties Company | Block copolymer melt-processable compositions, methods of their preparation, and articles therefrom |
| US20040122161A1 (en) * | 2002-12-21 | 2004-06-24 | Paul Charles W. | Hot melt adhesive based on acrylic block copolymers |
| IES20030294A2 (en) | 2003-04-17 | 2004-10-20 | Medtronic Vascular Connaught | Coating for biomedical devices |
| US7186789B2 (en) * | 2003-06-11 | 2007-03-06 | Advanced Cardiovascular Systems, Inc. | Bioabsorbable, biobeneficial polyester polymers for use in drug eluting stent coatings |
| US20050054774A1 (en) | 2003-09-09 | 2005-03-10 | Scimed Life Systems, Inc. | Lubricious coating |
| US7544381B2 (en) | 2003-09-09 | 2009-06-09 | Boston Scientific Scimed, Inc. | Lubricious coatings for medical device |
| US20050070688A1 (en) | 2003-09-26 | 2005-03-31 | 3M Innovative Properties Company | Reactive hydrophilic oligomers |
| US7807722B2 (en) * | 2003-11-26 | 2010-10-05 | Advanced Cardiovascular Systems, Inc. | Biobeneficial coating compositions and methods of making and using thereof |
| US8309112B2 (en) | 2003-12-24 | 2012-11-13 | Advanced Cardiovascular Systems, Inc. | Coatings for implantable medical devices comprising hydrophilic substances and methods for fabricating the same |
| US7771740B2 (en) * | 2004-07-19 | 2010-08-10 | Boston Scientific Scimed, Inc. | Medical devices containing copolymers with graft copolymer endblocks for drug delivery |
| US7919110B2 (en) * | 2005-01-25 | 2011-04-05 | Boston Scientific Scimed, Inc. | Medical device drug release regions containing non-covalently bound polymers |
| WO2006130776A2 (en) | 2005-06-02 | 2006-12-07 | Surmodics, Inc. | Hydrophilic polymeric coatings for medical articles |
| US20070155907A1 (en) | 2005-12-30 | 2007-07-05 | Zhao Jonathon Z | Biologically active block copolymers |
| US7622477B2 (en) | 2006-02-28 | 2009-11-24 | Cordis Corporation | Isomers and 42-epimers of rapamycin alkyl ether analogs, methods of making and using the same |
| US20090041923A1 (en) | 2007-08-06 | 2009-02-12 | Abbott Cardiovascular Systems Inc. | Medical device having a lubricious coating with a hydrophilic compound in an interlocking network |
| US8277826B2 (en) | 2008-06-25 | 2012-10-02 | Baxter International Inc. | Methods for making antimicrobial resins |
-
2004
- 2004-03-01 US US10/790,338 patent/US7655038B2/en not_active Ceased
- 2004-03-01 CA CA2519503A patent/CA2519503C/en not_active Expired - Lifetime
- 2004-03-01 AU AU2004216404A patent/AU2004216404C1/en not_active Ceased
- 2004-03-01 DK DK04715966.0T patent/DK1603603T3/en active
- 2004-03-01 WO PCT/IB2004/000534 patent/WO2004075943A1/en not_active Ceased
- 2004-03-01 PL PL04715966T patent/PL1603603T3/pl unknown
- 2004-03-01 EP EP20040715966 patent/EP1603603B1/en not_active Expired - Lifetime
- 2004-03-01 PT PT04715966T patent/PT1603603E/pt unknown
- 2004-03-01 EP EP14020085.8A patent/EP2918296A1/en not_active Withdrawn
- 2004-03-01 ES ES04715966T patent/ES2531326T3/es not_active Expired - Lifetime
- 2004-03-01 JP JP2006502480A patent/JP4791349B2/ja not_active Expired - Lifetime
-
2012
- 2012-02-02 US US13/365,092 patent/USRE45500E1/en active Active
-
2016
- 2016-03-16 HK HK16103055.8A patent/HK1215199A1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| USRE45500E1 (en) | 2015-04-28 |
| JP2006519049A (ja) | 2006-08-24 |
| HK1215199A1 (en) | 2016-08-19 |
| US7655038B2 (en) | 2010-02-02 |
| EP1603603A1 (en) | 2005-12-14 |
| EP2918296A1 (en) | 2015-09-16 |
| AU2004216404A1 (en) | 2004-09-10 |
| JP4791349B2 (ja) | 2011-10-12 |
| EP1603603B1 (en) | 2014-11-19 |
| PL1603603T3 (pl) | 2015-07-31 |
| AU2004216404C1 (en) | 2011-04-28 |
| US20040170752A1 (en) | 2004-09-02 |
| ES2531326T3 (es) | 2015-03-13 |
| WO2004075943A1 (en) | 2004-09-10 |
| DK1603603T3 (en) | 2015-02-23 |
| PT1603603E (pt) | 2015-02-24 |
| AU2004216404B2 (en) | 2010-11-25 |
| CA2519503A1 (en) | 2004-09-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2519503C (en) | Drug delivery from a polymer coating on a medical device | |
| JP5117724B2 (ja) | 親水性添加剤を含むステント用コーティング | |
| US8063151B2 (en) | Methods for manufacturing copolymers having 1-methyl-2-methoxyethyl moieties and use of same | |
| US8088404B2 (en) | Biocompatible controlled release coatings for medical devices and related methods | |
| EP1803754B1 (en) | Biologically active block copolymers and coated articles thereof | |
| EP1656163B1 (en) | Biocompatible controlled release coatings for medical devices and related methods | |
| US20050095267A1 (en) | Nanoparticle-based controlled release polymer coatings for medical implants | |
| US9056156B2 (en) | Medical devices comprising polymeric drug delivery systems with drug solubility gradients | |
| US8431665B2 (en) | Zwitterionic terpolymers, method of making and use on medical devices | |
| JP2006519049A5 (enExample) | ||
| US7815927B2 (en) | Terpolymers for controlled release of bioactive agents from implantable medical devices | |
| WO2007024500A1 (en) | Controlled radical polymerization-derived block copolymer compositions for medical device coatings | |
| CA2572262C (en) | A tri-branched biologically active copolymer |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20240301 |