ES2305512T3 - Copolimeros biodegradables de varios bloques, segmentados y de fases separadas. - Google Patents
Copolimeros biodegradables de varios bloques, segmentados y de fases separadas. Download PDFInfo
- Publication number
- ES2305512T3 ES2305512T3 ES03764248T ES03764248T ES2305512T3 ES 2305512 T3 ES2305512 T3 ES 2305512T3 ES 03764248 T ES03764248 T ES 03764248T ES 03764248 T ES03764248 T ES 03764248T ES 2305512 T3 ES2305512 T3 ES 2305512T3
- Authority
- ES
- Spain
- Prior art keywords
- prepolymer
- copolymer
- copolymers
- caprolactone
- prepolymers
- 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
- 229920001577 copolymer Polymers 0.000 title claims abstract description 153
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 claims description 58
- 239000000178 monomer Substances 0.000 claims description 51
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 27
- 239000004970 Chain extender Substances 0.000 claims description 23
- 238000002844 melting Methods 0.000 claims description 23
- 230000008018 melting Effects 0.000 claims description 23
- 238000009826 distribution Methods 0.000 claims description 19
- 229920001223 polyethylene glycol Polymers 0.000 claims description 19
- 239000002202 Polyethylene glycol Substances 0.000 claims description 18
- 150000002009 diols Chemical class 0.000 claims description 15
- 238000006116 polymerization reaction Methods 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 125000001931 aliphatic group Chemical group 0.000 claims description 13
- 230000008569 process Effects 0.000 claims description 13
- 229920000570 polyether Polymers 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 11
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 claims description 10
- 230000009477 glass transition Effects 0.000 claims description 10
- 210000005036 nerve Anatomy 0.000 claims description 10
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 9
- -1 cyclic anhydrides Chemical class 0.000 claims description 9
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 8
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 8
- 125000004122 cyclic group Chemical group 0.000 claims description 8
- 229940079593 drug Drugs 0.000 claims description 8
- 229920002732 Polyanhydride Polymers 0.000 claims description 7
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 7
- 239000004005 microsphere Substances 0.000 claims description 7
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical group C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 125000005442 diisocyanate group Chemical group 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 239000003999 initiator Substances 0.000 claims description 6
- 238000000576 coating method Methods 0.000 claims description 5
- RKDVKSZUMVYZHH-UHFFFAOYSA-N 1,4-dioxane-2,5-dione Chemical compound O=C1COC(=O)CO1 RKDVKSZUMVYZHH-UHFFFAOYSA-N 0.000 claims description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 4
- 239000007822 coupling agent Substances 0.000 claims description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 238000007151 ring opening polymerisation reaction Methods 0.000 claims description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 4
- KKGSHHDRPRINNY-UHFFFAOYSA-N 1,4-dioxan-2-one Chemical compound O=C1COCCO1.O=C1COCCO1 KKGSHHDRPRINNY-UHFFFAOYSA-N 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 238000005859 coupling reaction Methods 0.000 claims description 3
- 238000012377 drug delivery Methods 0.000 claims description 3
- 239000003480 eluent Substances 0.000 claims description 3
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- YFHICDDUDORKJB-UHFFFAOYSA-N trimethylene carbonate Chemical compound O=C1OCCCO1 YFHICDDUDORKJB-UHFFFAOYSA-N 0.000 claims description 3
- VKSWWACDZPRJAP-UHFFFAOYSA-N 1,3-dioxepan-2-one Chemical compound O=C1OCCCCO1 VKSWWACDZPRJAP-UHFFFAOYSA-N 0.000 claims description 2
- VPVXHAANQNHFSF-UHFFFAOYSA-N 1,4-dioxan-2-one Chemical compound O=C1COCCO1 VPVXHAANQNHFSF-UHFFFAOYSA-N 0.000 claims description 2
- AOLNDUQWRUPYGE-UHFFFAOYSA-N 1,4-dioxepan-5-one Chemical compound O=C1CCOCCO1 AOLNDUQWRUPYGE-UHFFFAOYSA-N 0.000 claims description 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims description 2
- SJZRECIVHVDYJC-UHFFFAOYSA-N 4-hydroxybutyric acid Chemical compound OCCCC(O)=O SJZRECIVHVDYJC-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 239000001361 adipic acid Substances 0.000 claims description 2
- 235000011037 adipic acid Nutrition 0.000 claims description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 2
- 125000005587 carbonate group Chemical group 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 claims description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 2
- 239000004310 lactic acid Substances 0.000 claims description 2
- 235000014655 lactic acid Nutrition 0.000 claims description 2
- 230000005499 meniscus Effects 0.000 claims description 2
- 239000005014 poly(hydroxyalkanoate) Substances 0.000 claims description 2
- 229920000903 polyhydroxyalkanoate Polymers 0.000 claims description 2
- FDYWJVHETVDSRA-UHFFFAOYSA-N 1,1-diisocyanatobutane Chemical compound CCCC(N=C=O)N=C=O FDYWJVHETVDSRA-UHFFFAOYSA-N 0.000 claims 2
- 239000007795 chemical reaction product Substances 0.000 claims 2
- 229920001451 polypropylene glycol Polymers 0.000 claims 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims 1
- 150000001991 dicarboxylic acids Chemical class 0.000 claims 1
- 229920001400 block copolymer Polymers 0.000 abstract description 24
- 229920000728 polyester Polymers 0.000 abstract description 24
- 230000007704 transition Effects 0.000 abstract description 14
- 229920001169 thermoplastic Polymers 0.000 abstract description 5
- 239000004416 thermosoftening plastic Substances 0.000 abstract description 5
- 239000012071 phase Substances 0.000 description 78
- 229920001634 Copolyester Polymers 0.000 description 52
- 229920001610 polycaprolactone Polymers 0.000 description 39
- 229920000642 polymer Polymers 0.000 description 33
- 239000000203 mixture Substances 0.000 description 31
- 229920005604 random copolymer Polymers 0.000 description 22
- 239000000243 solution Substances 0.000 description 17
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- 239000000463 material Substances 0.000 description 14
- 230000004927 fusion Effects 0.000 description 12
- 238000000113 differential scanning calorimetry Methods 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 230000015556 catabolic process Effects 0.000 description 10
- 238000006731 degradation reaction Methods 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 238000005809 transesterification reaction Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- JJTUDXZGHPGLLC-IMJSIDKUSA-N 4511-42-6 Chemical compound C[C@@H]1OC(=O)[C@H](C)OC1=O JJTUDXZGHPGLLC-IMJSIDKUSA-N 0.000 description 5
- 229920001244 Poly(D,L-lactide) Polymers 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 229920000954 Polyglycolide Polymers 0.000 description 4
- 239000004372 Polyvinyl alcohol Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- 229920001519 homopolymer Polymers 0.000 description 4
- 229920000515 polycarbonate Polymers 0.000 description 4
- 239000004417 polycarbonate Substances 0.000 description 4
- 229920002451 polyvinyl alcohol Polymers 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- ZAJGKKXBKLVSKW-UHFFFAOYSA-N 3,6-dimethyl-1,4-dioxane-2,5-dione;oxepan-2-one Chemical compound O=C1CCCCCO1.CC1OC(=O)C(C)OC1=O ZAJGKKXBKLVSKW-UHFFFAOYSA-N 0.000 description 3
- 239000004606 Fillers/Extenders Substances 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000012620 biological material Substances 0.000 description 3
- PBAYDYUZOSNJGU-UHFFFAOYSA-N chelidonic acid Natural products OC(=O)C1=CC(=O)C=C(C(O)=O)O1 PBAYDYUZOSNJGU-UHFFFAOYSA-N 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000005304 joining Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229920001432 poly(L-lactide) Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- 101100219382 Caenorhabditis elegans cah-2 gene Proteins 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 239000003708 ampul Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 238000012662 bulk polymerization Methods 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
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- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
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- 239000000806 elastomer Substances 0.000 description 1
- VYSYZMNJHYOXGN-UHFFFAOYSA-N ethyl n-aminocarbamate Chemical compound CCOC(=O)NN VYSYZMNJHYOXGN-UHFFFAOYSA-N 0.000 description 1
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- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 210000002435 tendon Anatomy 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
- A61K9/0024—Solid, semi-solid or solidifying implants, which are implanted or injected in body tissue
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
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- A—HUMAN NECESSITIES
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- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1629—Organic macromolecular compounds
- A61K9/1641—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, poloxamers
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1629—Organic macromolecular compounds
- A61K9/1641—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, poloxamers
- A61K9/1647—Polyesters, e.g. poly(lactide-co-glycolide)
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- 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
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/14—Macromolecular materials
- A61L27/18—Macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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- 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
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/28—Materials for coating prostheses
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- 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
- A61L31/06—Macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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- 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
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4266—Polycondensates having carboxylic or carbonic ester groups in the main chain prepared from hydroxycarboxylic acids and/or lactones
- C08G18/4269—Lactones
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
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- C08G63/08—Lactones or lactides
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/60—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from the reaction of a mixture of hydroxy carboxylic acids, polycarboxylic acids and polyhydroxy compounds
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/64—Polyesters containing both carboxylic ester groups and carbonate groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/664—Polyesters containing oxygen in the form of ether groups derived from hydroxy carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/04—Polyesters derived from hydroxycarboxylic acids, e.g. lactones
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2230/00—Compositions for preparing biodegradable polymers
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Epidemiology (AREA)
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- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Polyesters Or Polycarbonates (AREA)
- Materials For Medical Uses (AREA)
- Biological Depolymerization Polymers (AREA)
- Medicinal Preparation (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
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Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02077878 | 2002-07-16 | ||
| EP02077878A EP1382628A1 (en) | 2002-07-16 | 2002-07-16 | Biodegradable phase separated segmented/block co-polyesters |
| PCT/NL2003/000519 WO2004007588A1 (en) | 2002-07-16 | 2003-07-16 | Biodegradable phase separated segmented multi block co-polymers |
| EP03764248A EP1551899B1 (en) | 2002-07-16 | 2003-07-16 | Biodegradable phase separated segmented multi block co-polymers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2305512T3 true ES2305512T3 (es) | 2008-11-01 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES03764248T Expired - Lifetime ES2305512T3 (es) | 2002-07-16 | 2003-07-16 | Copolimeros biodegradables de varios bloques, segmentados y de fases separadas. |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8674033B2 (enExample) |
| EP (2) | EP1382628A1 (enExample) |
| JP (1) | JP2005533148A (enExample) |
| CN (1) | CN1675281B (enExample) |
| AT (1) | ATE394439T1 (enExample) |
| AU (1) | AU2003247231B2 (enExample) |
| CA (1) | CA2493375C (enExample) |
| DE (1) | DE60320819D1 (enExample) |
| ES (1) | ES2305512T3 (enExample) |
| WO (1) | WO2004007588A1 (enExample) |
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| US8685431B2 (en) * | 2004-03-16 | 2014-04-01 | Advanced Cardiovascular Systems, Inc. | Biologically absorbable coatings for implantable devices based on copolymers having ester bonds and methods for fabricating the same |
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| US8357391B2 (en) * | 2004-07-30 | 2013-01-22 | Advanced Cardiovascular Systems, Inc. | Coatings for implantable devices comprising poly (hydroxy-alkanoates) and diacid linkages |
| JP2008508414A (ja) | 2004-08-02 | 2008-03-21 | サムヤン コーポレーション | ゾル−ゲル遷移が可能な生分解性多重ブロック高分子組成物、及びこれを含有する薬学的組成物 |
| JP4870071B2 (ja) * | 2005-03-18 | 2012-02-08 | 三井化学株式会社 | 生分解性を有する水環境応答型ポリマー、その製造方法および水崩壊性材料 |
| DE102005033101A1 (de) | 2005-07-15 | 2007-01-25 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Resorbierbare Polyetherester und ihre Verwendung zur Herstellung von medizinischen Implantaten |
| US20070233219A1 (en) * | 2006-02-16 | 2007-10-04 | Bilal Shafi | Polymeric heart restraint |
| US9028859B2 (en) * | 2006-07-07 | 2015-05-12 | Advanced Cardiovascular Systems, Inc. | Phase-separated block copolymer coatings for implantable medical devices |
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| EP2049591A4 (en) * | 2006-08-02 | 2009-08-19 | Polynovo Biomaterials Pty Ltd | BIOKOMPATIBLE POLYMERIC COMPOSITIONS |
| GB0620685D0 (en) * | 2006-10-18 | 2006-11-29 | Controlled Therapeutics Sct | Bioresorbable polymers |
| EP2076211A4 (en) * | 2006-10-20 | 2015-07-22 | Elixir Medical Corp | LUMINOUS PROSTHESES AND METHODS OF COATING THEREOF |
| EP2073754A4 (en) | 2006-10-20 | 2012-09-26 | Orbusneich Medical Inc | BIOABSORBABLE POLYMER COMPOSITION AND MEDICAL DEVICE BACKGROUND |
| US7959942B2 (en) | 2006-10-20 | 2011-06-14 | Orbusneich Medical, Inc. | Bioabsorbable medical device with coating |
| DE102006058755A1 (de) * | 2006-12-08 | 2008-06-12 | Gkss-Forschungszentrum Geesthacht Gmbh | Verfahren zur Herstellung eines alternierenden Multiblockcopolymers mit Formgedächtnis |
| US8501290B2 (en) | 2008-01-15 | 2013-08-06 | Abbott Cardiovascular Systems Inc. | Implantable medical devices fabricated from polyurethanes with biodegradable hard and soft blocks and blends thereof |
| ATE548285T1 (de) | 2008-01-29 | 2012-03-15 | James Alexander Corp | Spender |
| US9259515B2 (en) | 2008-04-10 | 2016-02-16 | Abbott Cardiovascular Systems Inc. | Implantable medical devices fabricated from polyurethanes with grafted radiopaque groups |
| US20090326642A1 (en) * | 2008-06-25 | 2009-12-31 | Yunbing Wang | Implantable Medical Devices Fabricated From Radiopaque Polymers With High Fracture Toughness |
| JP5574445B2 (ja) * | 2009-03-06 | 2014-08-20 | 国立大学法人 岡山大学 | 生分解性多孔質中空微粒子、その製造方法および用途 |
| CN101531756B (zh) * | 2009-04-16 | 2011-06-15 | 山东大学 | 一种水溶性聚乙二醇/聚乳酸多嵌段聚碳酸酯的制备方法 |
| US8992601B2 (en) | 2009-05-20 | 2015-03-31 | 480 Biomedical, Inc. | Medical implants |
| US9309347B2 (en) | 2009-05-20 | 2016-04-12 | Biomedical, Inc. | Bioresorbable thermoset polyester/urethane elastomers |
| GB2475778B (en) * | 2009-05-20 | 2013-03-13 | Arsenal Medical Inc | Medical implant |
| US20110319987A1 (en) | 2009-05-20 | 2011-12-29 | Arsenal Medical | Medical implant |
| EP3858299B1 (en) | 2009-05-20 | 2025-10-08 | Lyra Therapeutics, Inc. | Method of loading a self-expanding implant |
| EP2480588B1 (en) * | 2009-09-18 | 2018-04-25 | BTG International Limited | Reconstitutable reverse thermal gelling polymers |
| US9155722B2 (en) * | 2009-09-18 | 2015-10-13 | Protherics Salt Lake City, Inc. | Reconstitutable reverse thermal gelling polymers |
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| EP2692368B1 (en) | 2011-03-30 | 2018-02-21 | Toray Industries, Inc. | Biodegradable particle, vascular embolization material and method for producing biodegradable particles |
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| US20130005829A1 (en) * | 2011-06-30 | 2013-01-03 | Advanced Technologies And Regenerative Medicine, Llc. | Segmented, epsilon-Caprolactone-Rich, Poly(epsilon-Caprolactone-co-p-Dioxanone) Copolymers for Medical Applications and Devices Therefrom |
| JP6174023B2 (ja) * | 2011-07-22 | 2017-08-02 | インノコア テクノロジーズ ビー．ブイ． | 生物活性化合物の制御放出のための生物分解性、半結晶性、相分離、熱可塑性マルチブロックコポリマー |
| AU2012313984B2 (en) * | 2011-09-30 | 2016-02-11 | Covidien Lp | Reversible stiffening of light weight mesh |
| JP5763565B2 (ja) | 2012-02-02 | 2015-08-12 | 住友ゴム工業株式会社 | 表面改質方法及び表面改質弾性体 |
| US20130236499A1 (en) * | 2012-03-12 | 2013-09-12 | Sasa Andjelic | Segmented, Semicrystalline Poly(Lactide-co-epsilon-Caprolactone) Absorbable Copolymers |
| JP5812935B2 (ja) | 2012-05-16 | 2015-11-17 | 住友ゴム工業株式会社 | 表面改質方法及び表面改質弾性体 |
| WO2014038688A1 (ja) | 2012-09-10 | 2014-03-13 | 住友ゴム工業株式会社 | 表面改質方法及び表面改質弾性体 |
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| JP6053482B2 (ja) | 2012-11-30 | 2016-12-27 | 住友ゴム工業株式会社 | 注射器用ガスケットの製造方法 |
| KR101560303B1 (ko) * | 2012-12-06 | 2015-10-14 | 주식회사 엘지화학 | 락타이드 공중합체, 이를 포함하는 수지 조성물 및 필름 |
| CN102977319B (zh) * | 2012-12-17 | 2014-09-03 | 中国科学院长春应用化学研究所 | 可降解聚乳酸两嵌段共聚物、制备方法及其在改性聚乳酸中的应用 |
| JP6105292B2 (ja) * | 2013-01-07 | 2017-03-29 | 住友ゴム工業株式会社 | 表面改質方法及び表面改質弾性体 |
| JP5816222B2 (ja) | 2013-04-25 | 2015-11-18 | 住友ゴム工業株式会社 | 表面改質方法及び表面改質弾性体 |
| CN103254411A (zh) * | 2013-06-07 | 2013-08-21 | 北京理工大学 | 一种高分子量聚乳酸的直接缩聚扩链制备方法 |
| JP5797239B2 (ja) | 2013-06-11 | 2015-10-21 | 住友ゴム工業株式会社 | 立体形状物の表面改質方法及び注射器用ガスケット |
| WO2014203668A1 (ja) | 2013-06-20 | 2014-12-24 | 住友ゴム工業株式会社 | 表面改質方法及び表面改質体 |
| WO2015030550A1 (ko) * | 2013-08-30 | 2015-03-05 | 주식회사 엘지화학 | 블록 공중합체 |
| EP3040354B1 (en) | 2013-08-30 | 2020-11-04 | LG Chem, Ltd. | Block copolymer |
| JP5820489B2 (ja) | 2014-01-06 | 2015-11-24 | 住友ゴム工業株式会社 | 表面改質方法及び表面改質弾性体 |
| JP6338504B2 (ja) | 2014-10-02 | 2018-06-06 | 住友ゴム工業株式会社 | 表面改質方法及び表面改質弾性体 |
| EP3034534A1 (en) * | 2014-12-17 | 2016-06-22 | PURAC Biochem BV | Substrates coated or bonded with a composition comprising a polyurethane |
| US12006395B2 (en) | 2015-01-02 | 2024-06-11 | Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. | Biodegradable polymer |
| JP6613692B2 (ja) | 2015-08-03 | 2019-12-04 | 住友ゴム工業株式会社 | 表面改質方法及び表面改質弾性体 |
| JP6551022B2 (ja) | 2015-08-03 | 2019-07-31 | 住友ゴム工業株式会社 | 表面改質方法及び表面改質体 |
| AU2018217064A1 (en) * | 2017-01-31 | 2019-08-08 | Veru Inc. | Compositions and methods for long term release of Gonadotropin-releasing hormone (GnRH) antagonists |
| EP3636292B1 (en) * | 2017-05-29 | 2023-03-01 | Educational Foundation Of Osaka Medical And Pharmaceutical University | Meniscus regeneration substrate |
| JP7484167B2 (ja) * | 2018-12-13 | 2024-05-16 | 東レ株式会社 | 医療用成形体、医療機器、神経再生誘導チューブ |
| CN109734869B (zh) * | 2018-12-25 | 2021-05-11 | 广东工业大学 | 一种聚醚酯聚氨酯及其制备方法和应用 |
| US20210017329A1 (en) * | 2019-07-19 | 2021-01-21 | Evonik Operations Gmbh | Multi-block shape memory bioresorbable polymers |
| AU2020357419B2 (en) | 2019-10-01 | 2025-12-04 | InnoCore Technologies Holding B.V. | Biodegradable, phase separated, thermoplastic multi-block copolymer |
| CN111205445B (zh) * | 2020-03-09 | 2021-07-16 | 成都颐合恒瑞医疗科技有限公司 | 一种双亲性嵌段共聚物、可吸收骨蜡及制法 |
| KR20240035841A (ko) * | 2021-08-19 | 2024-03-18 | 자빌 인코퍼레이티드 | 핵형성에 의한 폴리카프로락톤 분말의 제조 방법 |
| WO2024029491A1 (ja) * | 2022-08-01 | 2024-02-08 | Dic株式会社 | ３－ヒドロキシ酪酸からなるコポリエステル及びその製造方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5066772A (en) * | 1987-12-17 | 1991-11-19 | Allied-Signal Inc. | Medical devices fabricated totally or in part from copolymers of recurring units derived from cyclic carbonates and lactides |
| US5133739A (en) * | 1990-02-06 | 1992-07-28 | Ethicon, Inc. | Segmented copolymers of ε-caprolactone and glycolide |
| DE4005415C2 (de) * | 1990-02-21 | 1996-04-11 | Boehringer Ingelheim Kg | Verfahren zum Herstellen von Polyestern auf der Basis von Hydroxycarbonsäuren |
| NL9001984A (nl) * | 1990-09-10 | 1992-04-01 | Stamicarbon | Werkwijze voor het produceren van een voorwerp van een copolymeer van lactide en epsilon-caprolacton voor medische toepassingen. |
| US5236444A (en) * | 1992-10-27 | 1993-08-17 | United States Surgical Corporation | Absorbable polymers and surgical articles made therefrom |
| US5202413A (en) * | 1993-02-16 | 1993-04-13 | E. I. Du Pont De Nemours And Company | Alternating (ABA)N polylactide block copolymers |
| KR960015447B1 (ko) * | 1993-03-16 | 1996-11-14 | 주식회사 삼양사 | 의료용 생분해성 고분자 |
| US6211249B1 (en) * | 1997-07-11 | 2001-04-03 | Life Medical Sciences, Inc. | Polyester polyether block copolymers |
| AU751861B2 (en) * | 1998-02-23 | 2002-08-29 | Massachusetts Institute Of Technology | Biodegradable shape memory polymers |
| IL140049A0 (en) * | 1998-06-05 | 2002-02-10 | Polyganics Bv | Biomedical polyurethane, its preparation and use |
| JP2003327814A (ja) * | 2002-05-09 | 2003-11-19 | Daicel Chem Ind Ltd | 相溶性樹脂組成物 |
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- 2003-07-16 JP JP2004521291A patent/JP2005533148A/ja active Pending
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- 2003-07-16 EP EP03764248A patent/EP1551899B1/en not_active Expired - Lifetime
- 2003-07-16 AU AU2003247231A patent/AU2003247231B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JP2005533148A (ja) | 2005-11-04 |
| CA2493375A1 (en) | 2004-01-22 |
| US8674033B2 (en) | 2014-03-18 |
| US20070003592A1 (en) | 2007-01-04 |
| EP1382628A1 (en) | 2004-01-21 |
| WO2004007588A1 (en) | 2004-01-22 |
| ATE394439T1 (de) | 2008-05-15 |
| CA2493375C (en) | 2012-01-03 |
| CN1675281B (zh) | 2010-05-12 |
| AU2003247231A1 (en) | 2004-02-02 |
| CN1675281A (zh) | 2005-09-28 |
| EP1551899B1 (en) | 2008-05-07 |
| AU2003247231B2 (en) | 2008-07-31 |
| DE60320819D1 (de) | 2008-06-19 |
| EP1551899A1 (en) | 2005-07-13 |
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