CA2567194A1 - Absorbable biocompatible materials - Google Patents
Absorbable biocompatible materials Download PDFInfo
- Publication number
- CA2567194A1 CA2567194A1 CA002567194A CA2567194A CA2567194A1 CA 2567194 A1 CA2567194 A1 CA 2567194A1 CA 002567194 A CA002567194 A CA 002567194A CA 2567194 A CA2567194 A CA 2567194A CA 2567194 A1 CA2567194 A1 CA 2567194A1
- Authority
- CA
- Canada
- Prior art keywords
- group
- copolymer
- coating
- monomer unit
- hydrophobic
- 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.)
- Abandoned
Links
- 239000000560 biocompatible material Substances 0.000 title description 2
- 239000003814 drug Substances 0.000 claims abstract description 77
- 150000001413 amino acids Chemical class 0.000 claims abstract description 66
- 229940124597 therapeutic agent Drugs 0.000 claims abstract description 63
- 238000000576 coating method Methods 0.000 claims abstract description 60
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 60
- 229920001577 copolymer Polymers 0.000 claims abstract description 59
- 238000000034 method Methods 0.000 claims abstract description 59
- 239000011248 coating agent Substances 0.000 claims abstract description 46
- 239000002253 acid Substances 0.000 claims abstract description 29
- 238000002513 implantation Methods 0.000 claims abstract description 8
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 14
- 229920000642 polymer Polymers 0.000 claims description 69
- -1 oxime ester Chemical class 0.000 claims description 47
- 239000000178 monomer Substances 0.000 claims description 33
- 125000000524 functional group Chemical group 0.000 claims description 27
- 125000003277 amino group Chemical group 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- 229920001308 poly(aminoacid) Polymers 0.000 claims description 20
- 150000002430 hydrocarbons Chemical class 0.000 claims description 19
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 229930195733 hydrocarbon Natural products 0.000 claims description 15
- 125000005647 linker group Chemical group 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000000304 alkynyl group Chemical group 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 108010039918 Polylysine Proteins 0.000 claims description 11
- 229920000656 polylysine Polymers 0.000 claims description 11
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 125000003368 amide group Chemical group 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 229920001519 homopolymer Polymers 0.000 claims description 8
- 239000004215 Carbon black (E152) Substances 0.000 claims description 7
- 150000008064 anhydrides Chemical class 0.000 claims description 7
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- 229920002643 polyglutamic acid Polymers 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 108010020346 Polyglutamic Acid Proteins 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 6
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical group [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 5
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims description 5
- 230000009477 glass transition Effects 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 5
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 4
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 3
- 229910019142 PO4 Inorganic materials 0.000 claims description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 3
- 125000003636 chemical group Chemical group 0.000 claims description 3
- 238000004132 cross linking Methods 0.000 claims description 3
- 150000004676 glycans Chemical class 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 3
- 239000010452 phosphate Substances 0.000 claims description 3
- 108010064470 polyaspartate Proteins 0.000 claims description 3
- 229920001282 polysaccharide Polymers 0.000 claims description 3
- 239000005017 polysaccharide Substances 0.000 claims description 3
- 229920000805 Polyaspartic acid Polymers 0.000 claims 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 2
- 125000003275 alpha amino acid group Chemical group 0.000 claims 2
- 239000007864 aqueous solution Substances 0.000 claims 2
- 239000004202 carbamide Substances 0.000 claims 2
- 108090000765 processed proteins & peptides Proteins 0.000 abstract description 54
- 102000004196 processed proteins & peptides Human genes 0.000 abstract description 53
- 229920001184 polypeptide Polymers 0.000 abstract description 51
- 239000000463 material Substances 0.000 abstract description 28
- 239000002904 solvent Substances 0.000 abstract description 15
- 239000012876 carrier material Substances 0.000 abstract description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
- 239000010410 layer Substances 0.000 description 59
- 229940024606 amino acid Drugs 0.000 description 53
- 235000001014 amino acid Nutrition 0.000 description 53
- 239000000243 solution Substances 0.000 description 32
- 239000003795 chemical substances by application Substances 0.000 description 28
- 239000000203 mixture Substances 0.000 description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 26
- 239000000047 product Substances 0.000 description 24
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 21
- 229920000729 poly(L-lysine) polymer Polymers 0.000 description 21
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 125000001931 aliphatic group Chemical group 0.000 description 18
- 239000000126 substance Substances 0.000 description 18
- 229930012538 Paclitaxel Natural products 0.000 description 17
- 230000015572 biosynthetic process Effects 0.000 description 17
- 229960001592 paclitaxel Drugs 0.000 description 17
- 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 description 17
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
- 238000003786 synthesis reaction Methods 0.000 description 16
- 125000001424 substituent group Chemical group 0.000 description 15
- 229940079593 drug Drugs 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 11
- 239000004472 Lysine Substances 0.000 description 11
- 238000006467 substitution reaction Methods 0.000 description 11
- 125000004429 atom Chemical group 0.000 description 10
- 230000008569 process Effects 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- NHJVRSWLHSJWIN-UHFFFAOYSA-N 2,4,6-trinitrobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O NHJVRSWLHSJWIN-UHFFFAOYSA-N 0.000 description 8
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 8
- 230000015556 catabolic process Effects 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 238000006731 degradation reaction Methods 0.000 description 8
- 229940049906 glutamate Drugs 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 8
- 229960004592 isopropanol Drugs 0.000 description 8
- 238000011068 loading method Methods 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 150000001345 alkine derivatives Chemical class 0.000 description 7
- 238000005227 gel permeation chromatography Methods 0.000 description 7
- 229930195712 glutamate Natural products 0.000 description 7
- 125000001165 hydrophobic group Chemical group 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000002202 Polyethylene glycol Substances 0.000 description 6
- 150000001336 alkenes Chemical class 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 238000007385 chemical modification Methods 0.000 description 6
- 238000000338 in vitro Methods 0.000 description 6
- 238000010348 incorporation Methods 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 6
- 229920001223 polyethylene glycol Polymers 0.000 description 6
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 5
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 5
- 150000001335 aliphatic alkanes Chemical class 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 239000000032 diagnostic agent Substances 0.000 description 5
- 229940039227 diagnostic agent Drugs 0.000 description 5
- 238000009826 distribution Methods 0.000 description 5
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 5
- 239000010408 film Substances 0.000 description 5
- 235000018977 lysine Nutrition 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 239000008363 phosphate buffer Substances 0.000 description 5
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 4
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000002835 absorbance Methods 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 235000004279 alanine Nutrition 0.000 description 4
- 238000006065 biodegradation reaction Methods 0.000 description 4
- 229920001400 block copolymer Polymers 0.000 description 4
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 4
- 229960004132 diethyl ether Drugs 0.000 description 4
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
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- 238000005507 spraying Methods 0.000 description 4
- 230000002792 vascular Effects 0.000 description 4
- 239000003981 vehicle Substances 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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- 229920005603 alternating copolymer Polymers 0.000 description 3
- 125000004104 aryloxy group Chemical group 0.000 description 3
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- 238000003556 assay Methods 0.000 description 3
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- 229910021538 borax Inorganic materials 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 3
- UQGFMSUEHSUPRD-UHFFFAOYSA-N disodium;3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound [Na+].[Na+].O1B([O-])OB2OB([O-])OB1O2 UQGFMSUEHSUPRD-UHFFFAOYSA-N 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
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- 239000007943 implant Substances 0.000 description 3
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- 239000012528 membrane Substances 0.000 description 3
- 239000002953 phosphate buffered saline Substances 0.000 description 3
- 150000003904 phospholipids Chemical class 0.000 description 3
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- 238000002360 preparation method Methods 0.000 description 3
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- 210000001519 tissue Anatomy 0.000 description 3
- MEXAGTSTSPYCEP-JEDNCBNOSA-N (2s)-2,6-diaminohexanoic acid;hydrobromide Chemical compound Br.NCCCC[C@H](N)C(O)=O MEXAGTSTSPYCEP-JEDNCBNOSA-N 0.000 description 2
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 2
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- 102100022258 Disks large homolog 5 Human genes 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
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- 239000005639 Lauric acid Substances 0.000 description 2
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- MBMBGCFOFBJSGT-KUBAVDMBSA-N all-cis-docosa-4,7,10,13,16,19-hexaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O MBMBGCFOFBJSGT-KUBAVDMBSA-N 0.000 description 2
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
- 229960005261 aspartic acid Drugs 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 238000003618 dip coating Methods 0.000 description 2
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- HFJRKMMYBMWEAD-UHFFFAOYSA-N dodecanal Chemical compound CCCCCCCCCCCC=O HFJRKMMYBMWEAD-UHFFFAOYSA-N 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000006870 function Effects 0.000 description 2
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- 210000003709 heart valve Anatomy 0.000 description 2
- GOQYKNQRPGWPLP-UHFFFAOYSA-N heptadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- BTFJIXJJCSYFAL-UHFFFAOYSA-N icosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCO BTFJIXJJCSYFAL-UHFFFAOYSA-N 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
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- 150000002513 isocyanates Chemical class 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US57425004P | 2004-05-25 | 2004-05-25 | |
| US60/574,250 | 2004-05-25 | ||
| PCT/GB2005/002081 WO2005115492A1 (en) | 2004-05-25 | 2005-05-25 | Absorbable biocompatible materials |
Publications (1)
| Publication Number | Publication Date |
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| CA2567194A1 true CA2567194A1 (en) | 2005-12-08 |
Family
ID=35056943
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002567194A Abandoned CA2567194A1 (en) | 2004-05-25 | 2005-05-25 | Absorbable biocompatible materials |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20060134166A1 (enExample) |
| EP (1) | EP1748805B1 (enExample) |
| JP (1) | JP2008502376A (enExample) |
| CN (1) | CN1956742A (enExample) |
| AT (1) | ATE437664T1 (enExample) |
| AU (1) | AU2005247140A1 (enExample) |
| CA (1) | CA2567194A1 (enExample) |
| DE (1) | DE602005015696D1 (enExample) |
| WO (1) | WO2005115492A1 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009520040A (ja) | 2005-12-19 | 2009-05-21 | ファーマイン コーポレーション | 治療薬の送達のための疎水性コアの担体組成物、及び同担体組成物の作製法及び使用法 |
| US7858337B2 (en) * | 2007-03-08 | 2010-12-28 | Novartis Ag | Process for the manufacture of a composite material |
| US20090176892A1 (en) * | 2008-01-09 | 2009-07-09 | Pharmain Corporation | Soluble Hydrophobic Core Carrier Compositions for Delivery of Therapeutic Agents, Methods of Making and Using the Same |
| WO2010143646A1 (ja) * | 2009-06-09 | 2010-12-16 | 味の素株式会社 | 繊維構造体 |
| JP5770727B2 (ja) * | 2010-06-16 | 2015-08-26 | テルモ株式会社 | 医療用具の製造方法 |
| JP5910505B2 (ja) * | 2010-12-06 | 2016-04-27 | 味の素株式会社 | 医療用材料及びその製造方法 |
| JP6042876B2 (ja) * | 2012-03-27 | 2016-12-14 | テルモ株式会社 | コーティング組成物および医療機器 |
| WO2013146376A1 (ja) * | 2012-03-27 | 2013-10-03 | テルモ株式会社 | コーティング組成物および医療機器 |
| USRE49528E1 (en) | 2013-04-26 | 2023-05-16 | Biointeractions Ltd. | Bioactive coatings |
| CN105517585B (zh) | 2013-04-26 | 2019-11-22 | 生物相互作用有限公司 | 生物活性涂层 |
| CN105797220B (zh) * | 2014-12-31 | 2020-07-31 | 先健科技(深圳)有限公司 | 可降解铁基合金支架 |
| US10945997B2 (en) * | 2016-01-08 | 2021-03-16 | Nippon Kayaku Kabushiki Kaisha | Polymer derivative of macrolide immunosuppressant |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0179023B1 (fr) * | 1984-10-19 | 1991-01-23 | Battelle Memorial Institute | Polypeptide biodégradable et son utilisation pour le relargage progressif de médicaments |
| JPH01170464A (ja) * | 1987-12-25 | 1989-07-05 | Lion Corp | 生体材料 |
| DE69841937D1 (de) * | 1997-04-21 | 2010-11-25 | California Inst Of Techn | Multifunctionelle polymer-beschichtung |
| GB9811059D0 (en) * | 1998-05-23 | 1998-07-22 | Univ Strathclyde | Polyamino acid vesicles |
| US20030064965A1 (en) * | 2001-10-02 | 2003-04-03 | Jacob Richter | Method of delivering drugs to a tissue using drug-coated medical devices |
| CN1194704C (zh) * | 2001-11-12 | 2005-03-30 | 华东理工大学 | 含有活性药物、主链中具有氨基酸的聚酯及其制备方法 |
| AU2002233097A1 (en) * | 2002-02-28 | 2003-09-09 | Eidgenossische Technische Hochschule Zurich Oberflachentechnik | Biomedical implant surfaces with osteogenic properties |
| 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 |
-
2005
- 2005-05-24 US US11/136,340 patent/US20060134166A1/en not_active Abandoned
- 2005-05-25 EP EP05746512A patent/EP1748805B1/en not_active Expired - Lifetime
- 2005-05-25 WO PCT/GB2005/002081 patent/WO2005115492A1/en not_active Ceased
- 2005-05-25 AT AT05746512T patent/ATE437664T1/de not_active IP Right Cessation
- 2005-05-25 AU AU2005247140A patent/AU2005247140A1/en not_active Abandoned
- 2005-05-25 DE DE602005015696T patent/DE602005015696D1/de not_active Expired - Fee Related
- 2005-05-25 CN CNA2005800168088A patent/CN1956742A/zh active Pending
- 2005-05-25 CA CA002567194A patent/CA2567194A1/en not_active Abandoned
- 2005-05-25 JP JP2007514098A patent/JP2008502376A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| EP1748805A1 (en) | 2007-02-07 |
| JP2008502376A (ja) | 2008-01-31 |
| EP1748805B1 (en) | 2009-07-29 |
| ATE437664T1 (de) | 2009-08-15 |
| CN1956742A (zh) | 2007-05-02 |
| WO2005115492A1 (en) | 2005-12-08 |
| AU2005247140A1 (en) | 2005-12-08 |
| DE602005015696D1 (de) | 2009-09-10 |
| US20060134166A1 (en) | 2006-06-22 |
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Legal Events
| Date | Code | Title | Description |
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| FZDE | Discontinued |