ES2655656T3 - Biomateriales adecuados para usar como implantes detectables mediante imagen de resonancia magnética, eluyentes de fármacos para oclusión vascular - Google Patents
Biomateriales adecuados para usar como implantes detectables mediante imagen de resonancia magnética, eluyentes de fármacos para oclusión vascular Download PDFInfo
- Publication number
- ES2655656T3 ES2655656T3 ES13794343.7T ES13794343T ES2655656T3 ES 2655656 T3 ES2655656 T3 ES 2655656T3 ES 13794343 T ES13794343 T ES 13794343T ES 2655656 T3 ES2655656 T3 ES 2655656T3
- Authority
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- Spain
- Prior art keywords
- weight
- acrylamide
- drug
- iron oxide
- polymer
- 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.)
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Links
- 229940079593 drug Drugs 0.000 title claims abstract description 129
- 239000003814 drug Substances 0.000 title claims abstract description 129
- 239000012620 biological material Substances 0.000 title claims abstract description 87
- 239000007943 implant Substances 0.000 title claims abstract description 40
- 206010053648 Vascular occlusion Diseases 0.000 title claims abstract description 39
- 208000021331 vascular occlusion disease Diseases 0.000 title claims abstract description 39
- 238000002595 magnetic resonance imaging Methods 0.000 title claims abstract description 36
- 239000003480 eluent Substances 0.000 title description 5
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims abstract description 220
- 229920000642 polymer Polymers 0.000 claims abstract description 109
- MVBJSQCJPSRKSW-UHFFFAOYSA-N n-[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]prop-2-enamide Chemical compound OCC(CO)(CO)NC(=O)C=C MVBJSQCJPSRKSW-UHFFFAOYSA-N 0.000 claims abstract description 77
- CYUZOYPRAQASLN-UHFFFAOYSA-N 3-prop-2-enoyloxypropanoic acid Chemical compound OC(=O)CCOC(=O)C=C CYUZOYPRAQASLN-UHFFFAOYSA-N 0.000 claims abstract description 68
- PQUXFUBNSYCQAL-UHFFFAOYSA-N 1-(2,3-difluorophenyl)ethanone Chemical compound CC(=O)C1=CC=CC(F)=C1F PQUXFUBNSYCQAL-UHFFFAOYSA-N 0.000 claims abstract description 66
- 229940047670 sodium acrylate Drugs 0.000 claims abstract description 66
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 claims abstract description 63
- NLVXSWCKKBEXTG-UHFFFAOYSA-M ethenesulfonate Chemical compound [O-]S(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-M 0.000 claims abstract description 58
- 239000002245 particle Substances 0.000 claims abstract description 54
- 239000004005 microsphere Substances 0.000 claims description 169
- 239000000203 mixture Substances 0.000 claims description 139
- 239000000178 monomer Substances 0.000 claims description 118
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 claims description 76
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims description 74
- 239000011837 N,N-methylenebisacrylamide Substances 0.000 claims description 71
- 229920000536 2-Acrylamido-2-methylpropane sulfonic acid Polymers 0.000 claims description 49
- 229960004679 doxorubicin Drugs 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 32
- 239000000725 suspension Substances 0.000 claims description 28
- 239000002246 antineoplastic agent Substances 0.000 claims description 24
- 230000000379 polymerizing effect Effects 0.000 claims description 24
- UWKQSNNFCGGAFS-XIFFEERXSA-N irinotecan Chemical compound C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 UWKQSNNFCGGAFS-XIFFEERXSA-N 0.000 claims description 23
- 229940044683 chemotherapy drug Drugs 0.000 claims description 22
- 229960004768 irinotecan Drugs 0.000 claims description 22
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 54
- 239000003431 cross linking reagent Substances 0.000 description 36
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 32
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 28
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 21
- 229940048053 acrylate Drugs 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 239000003921 oil Substances 0.000 description 20
- 229920001577 copolymer Polymers 0.000 description 19
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 18
- 206010028980 Neoplasm Diseases 0.000 description 17
- 239000011780 sodium chloride Substances 0.000 description 17
- 238000002474 experimental method Methods 0.000 description 16
- 239000006228 supernatant Substances 0.000 description 16
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 14
- CUNWUEBNSZSNRX-RKGWDQTMSA-N (2r,3r,4r,5s)-hexane-1,2,3,4,5,6-hexol;(z)-octadec-9-enoic acid Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O CUNWUEBNSZSNRX-RKGWDQTMSA-N 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 238000000502 dialysis Methods 0.000 description 11
- SZVJSHCCFOBDDC-UHFFFAOYSA-N ferrosoferric oxide Chemical group O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 description 11
- 239000002105 nanoparticle Substances 0.000 description 11
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 10
- -1 sodium acrylate Chemical compound 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 210000004204 blood vessel Anatomy 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 238000001033 granulometry Methods 0.000 description 8
- 229960005078 sorbitan sesquioleate Drugs 0.000 description 8
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 7
- 210000001367 artery Anatomy 0.000 description 7
- 239000012528 membrane Substances 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- 239000001632 sodium acetate Substances 0.000 description 7
- 235000017281 sodium acetate Nutrition 0.000 description 7
- 239000005662 Paraffin oil Substances 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000003213 activating effect Effects 0.000 description 6
- 238000011068 loading method Methods 0.000 description 6
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 5
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 5
- 238000010908 decantation Methods 0.000 description 5
- WTFXARWRTYJXII-UHFFFAOYSA-N iron(2+);iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[Fe+2].[Fe+3].[Fe+3] WTFXARWRTYJXII-UHFFFAOYSA-N 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 description 4
- 238000010191 image analysis Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 210000002767 hepatic artery Anatomy 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 238000004007 reversed phase HPLC Methods 0.000 description 3
- 238000000825 ultraviolet detection Methods 0.000 description 3
- ZODNDDPVCIAZIQ-UHFFFAOYSA-N (2-hydroxy-3-prop-2-enoyloxypropyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)COC(=O)C=C ZODNDDPVCIAZIQ-UHFFFAOYSA-N 0.000 description 2
- YERHJBPPDGHCRJ-UHFFFAOYSA-N 1-[4-(1-oxoprop-2-enyl)-1-piperazinyl]-2-propen-1-one Chemical compound C=CC(=O)N1CCN(C(=O)C=C)CC1 YERHJBPPDGHCRJ-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
- MWWSFMDVAYGXBV-RUELKSSGSA-N Doxorubicin hydrochloride Chemical compound Cl.O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 MWWSFMDVAYGXBV-RUELKSSGSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 206010019695 Hepatic neoplasm Diseases 0.000 description 2
- ZRKLEAHGBNDKHM-UHFFFAOYSA-N N,n'-diallyl-2,3-dihydroxysuccinamide Chemical compound C=CCNC(=O)C(O)C(O)C(=O)NCC=C ZRKLEAHGBNDKHM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229940127089 cytotoxic agent Drugs 0.000 description 2
- 230000010102 embolization Effects 0.000 description 2
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 2
- 208000014018 liver neoplasm Diseases 0.000 description 2
- 239000011859 microparticle Substances 0.000 description 2
- PSUHXVMFHGPIJX-UHFFFAOYSA-N piperazine prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.C1CNCCN1 PSUHXVMFHGPIJX-UHFFFAOYSA-N 0.000 description 2
- SXGZJKUKBWWHRA-UHFFFAOYSA-N 2-(N-morpholiniumyl)ethanesulfonate Chemical compound [O-]S(=O)(=O)CC[NH+]1CCOCC1 SXGZJKUKBWWHRA-UHFFFAOYSA-N 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- 208000005189 Embolism Diseases 0.000 description 1
- 239000002147 L01XE04 - Sunitinib Substances 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000004037 angiogenesis inhibitor Substances 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 230000036770 blood supply Effects 0.000 description 1
- 210000002302 brachial artery Anatomy 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- BRXCDHOLJPJLLT-UHFFFAOYSA-N butane-2-sulfonic acid Chemical compound CCC(C)S(O)(=O)=O BRXCDHOLJPJLLT-UHFFFAOYSA-N 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 210000001105 femoral artery Anatomy 0.000 description 1
- 230000005294 ferromagnetic effect Effects 0.000 description 1
- 238000002594 fluoroscopy Methods 0.000 description 1
- 230000002440 hepatic effect Effects 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000007373 indentation Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 125000003010 ionic group Chemical group 0.000 description 1
- LIKBJVNGSGBSGK-UHFFFAOYSA-N iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Fe+3].[Fe+3] LIKBJVNGSGBSGK-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- BWYYYTVSBPRQCN-UHFFFAOYSA-M sodium;ethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=C BWYYYTVSBPRQCN-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- WINHZLLDWRZWRT-ATVHPVEESA-N sunitinib Chemical compound CCN(CC)CCNC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C WINHZLLDWRZWRT-ATVHPVEESA-N 0.000 description 1
- 229960001796 sunitinib Drugs 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229940086542 triethylamine Drugs 0.000 description 1
- 210000005166 vasculature Anatomy 0.000 description 1
Classifications
-
- 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
- A61K47/50—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/69—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
- A61K47/6921—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit the form being a particulate, a powder, an adsorbate, a bead or a sphere
- A61K47/6927—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit the form being a particulate, a powder, an adsorbate, a bead or a sphere the form being a solid microparticle having no hollow or gas-filled cores
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/06—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations
- A61K49/18—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by a special physical form, e.g. emulsions, microcapsules, liposomes
- A61K49/1818—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by a special physical form, e.g. emulsions, microcapsules, liposomes particles, e.g. uncoated or non-functionalised microparticles or nanoparticles
- A61K49/1821—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by a special physical form, e.g. emulsions, microcapsules, liposomes particles, e.g. uncoated or non-functionalised microparticles or nanoparticles coated or functionalised microparticles or nanoparticles
- A61K49/1824—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by a special physical form, e.g. emulsions, microcapsules, liposomes particles, e.g. uncoated or non-functionalised microparticles or nanoparticles coated or functionalised microparticles or nanoparticles coated or functionalised nanoparticles
- A61K49/1827—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by a special physical form, e.g. emulsions, microcapsules, liposomes particles, e.g. uncoated or non-functionalised microparticles or nanoparticles coated or functionalised microparticles or nanoparticles coated or functionalised nanoparticles having a (super)(para)magnetic core, being a solid MRI-active material, e.g. magnetite, or composed of a plurality of MRI-active, organic agents, e.g. Gd-chelates, or nuclei, e.g. Eu3+, encapsulated or entrapped in the core of the coated or functionalised nanoparticle
- A61K49/1851—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by a special physical form, e.g. emulsions, microcapsules, liposomes particles, e.g. uncoated or non-functionalised microparticles or nanoparticles coated or functionalised microparticles or nanoparticles coated or functionalised nanoparticles having a (super)(para)magnetic core, being a solid MRI-active material, e.g. magnetite, or composed of a plurality of MRI-active, organic agents, e.g. Gd-chelates, or nuclei, e.g. Eu3+, encapsulated or entrapped in the core of the coated or functionalised nanoparticle having a (super)(para)magnetic core coated or functionalised with an organic macromolecular compound, i.e. oligomeric, polymeric, dendrimeric organic molecule
- A61K49/1854—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by a special physical form, e.g. emulsions, microcapsules, liposomes particles, e.g. uncoated or non-functionalised microparticles or nanoparticles coated or functionalised microparticles or nanoparticles coated or functionalised nanoparticles having a (super)(para)magnetic core, being a solid MRI-active material, e.g. magnetite, or composed of a plurality of MRI-active, organic agents, e.g. Gd-chelates, or nuclei, e.g. Eu3+, encapsulated or entrapped in the core of the coated or functionalised nanoparticle having a (super)(para)magnetic core coated or functionalised with an organic macromolecular compound, i.e. oligomeric, polymeric, dendrimeric organic molecule the organic macromolecular compound being obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. poly(meth)acrylate, polyacrylamide, polyvinylpyrrolidone, polyvinylalcohol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nanotechnology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Molecular Biology (AREA)
- Immunology (AREA)
- Radiology & Medical Imaging (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Medicinal Preparation (AREA)
- Materials For Medical Uses (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261651389P | 2012-05-24 | 2012-05-24 | |
| US201261651389P | 2012-05-24 | ||
| PCT/US2013/042363 WO2013177364A1 (en) | 2012-05-24 | 2013-05-23 | Biomaterials suitable for use as drug eluting, magnetic resonance imaging detectable implants for vascular occlusion |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2655656T3 true ES2655656T3 (es) | 2018-02-21 |
Family
ID=49621771
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES13794343.7T Active ES2655656T3 (es) | 2012-05-24 | 2013-05-23 | Biomateriales adecuados para usar como implantes detectables mediante imagen de resonancia magnética, eluyentes de fármacos para oclusión vascular |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US10695440B2 (https=) |
| EP (2) | EP2854869B1 (https=) |
| JP (1) | JP6208749B2 (https=) |
| BR (1) | BR112014029149A2 (https=) |
| CA (1) | CA2866896C (https=) |
| ES (1) | ES2655656T3 (https=) |
| WO (1) | WO2013177364A1 (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013177364A1 (en) | 2012-05-24 | 2013-11-28 | Biosphere Medical, Inc. | Biomaterials suitable for use as drug eluting, magnetic resonance imaging detectable implants for vascular occlusion |
| JP6641265B2 (ja) | 2013-09-19 | 2020-02-05 | マイクロベンション インコーポレイテッドＭｉｃｒｏｖｅｎｔｉｏｎ， Ｉｎｃ． | ポリマーフィルム |
| EP3046952B1 (en) | 2013-09-19 | 2021-05-12 | Terumo Corporation | Polymer particles |
| EP3065719A4 (en) | 2013-11-08 | 2017-08-09 | Terumo Corporation | Polymer particles |
| WO2016154592A1 (en) | 2015-03-26 | 2016-09-29 | Microvention, Inc. | Embiolic particles |
| EP4279139A3 (en) | 2016-09-28 | 2024-01-24 | Terumo Corporation | Polymer particles |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS509858A (https=) | 1973-06-02 | 1975-01-31 | ||
| JPS6056676B2 (ja) | 1980-07-18 | 1985-12-11 | 日立造船株式会社 | コンクリ−ト複合パネル |
| ATE130517T1 (de) | 1990-08-08 | 1995-12-15 | Takeda Chemical Industries Ltd | Intravaskulär embolisierendes mittel mit gehalt an einem die angiogenesis hemmenden stoff. |
| FR2676927B1 (fr) * | 1991-05-29 | 1995-06-23 | Ibf | Microspheres utilisables pour les occlusions vasculaires therapeutiques et solutions injectables les contenant. |
| US5514379A (en) | 1992-08-07 | 1996-05-07 | The General Hospital Corporation | Hydrogel compositions and methods of use |
| US6315709B1 (en) | 1998-08-07 | 2001-11-13 | Stereotaxis, Inc. | Magnetic vascular defect treatment system |
| KR100872884B1 (ko) | 2000-03-24 | 2008-12-10 | 바이오스피어 메디칼 인코포레이티드 | 능동 색전화용 미소구 |
| FR2808026B1 (fr) * | 2000-04-25 | 2002-06-14 | Alexandre Laurent | Biomateriau a base de polymere hydrophile presentant un signal specifique en imagerie par resonance magnetique et procede de preparation d'un tel biomateriau |
| JP2005053707A (ja) | 2001-07-30 | 2005-03-03 | Kankyo Device Kenkyusho:Kk | 可視光応答性材料の製造方法 |
| US7462366B2 (en) * | 2002-03-29 | 2008-12-09 | Boston Scientific Scimed, Inc. | Drug delivery particle |
| US8012454B2 (en) | 2002-08-30 | 2011-09-06 | Boston Scientific Scimed, Inc. | Embolization |
| US20040161466A1 (en) * | 2003-02-14 | 2004-08-19 | Biocompatibles Uk Limited | Chemoembolisation |
| JP4909071B2 (ja) | 2003-03-24 | 2012-04-04 | プルーローメッド， インコーポレイテッド | 逆感熱性ポリマーを使用する一時的な塞栓形成 |
| WO2005044224A2 (en) | 2003-05-02 | 2005-05-19 | Case Western Reserve University | Drug delivery system based on polymer nanoshells |
| EP2202250B1 (en) * | 2004-08-19 | 2013-10-09 | Covidien LP | Water-swellable copolymers and articles and coating made therefrom |
| EP2229147A2 (en) * | 2007-12-03 | 2010-09-22 | The Johns Hopkins University | Methods of synthesis and use of chemospheres |
| GB0807154D0 (en) * | 2008-04-18 | 2008-05-21 | Univ Aston | Intervertebral disc |
| JP5792714B2 (ja) * | 2009-05-28 | 2015-10-14 | コーニング インコーポレイテッド | 細胞培養のための膨潤性の合成マイクロキャリア |
| EP2451488A2 (en) * | 2009-07-07 | 2012-05-16 | Bartling, Sönke | Multimodal visible polymer embolization material |
| WO2013177364A1 (en) | 2012-05-24 | 2013-11-28 | Biosphere Medical, Inc. | Biomaterials suitable for use as drug eluting, magnetic resonance imaging detectable implants for vascular occlusion |
-
2013
- 2013-05-23 WO PCT/US2013/042363 patent/WO2013177364A1/en not_active Ceased
- 2013-05-23 BR BR112014029149A patent/BR112014029149A2/pt not_active Application Discontinuation
- 2013-05-23 ES ES13794343.7T patent/ES2655656T3/es active Active
- 2013-05-23 EP EP13794343.7A patent/EP2854869B1/en active Active
- 2013-05-23 JP JP2015514174A patent/JP6208749B2/ja active Active
- 2013-05-23 EP EP17193907.7A patent/EP3295961B1/en active Active
- 2013-05-23 US US13/900,796 patent/US10695440B2/en active Active
- 2013-05-23 CA CA2866896A patent/CA2866896C/en active Active
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|---|---|
| US20130315838A1 (en) | 2013-11-28 |
| US10695440B2 (en) | 2020-06-30 |
| EP3295961B1 (en) | 2020-04-08 |
| WO2013177364A1 (en) | 2013-11-28 |
| JP2015517390A (ja) | 2015-06-22 |
| EP3295961A1 (en) | 2018-03-21 |
| EP2854869A1 (en) | 2015-04-08 |
| JP6208749B2 (ja) | 2017-10-04 |
| BR112014029149A2 (pt) | 2017-06-27 |
| CA2866896C (en) | 2021-01-26 |
| EP2854869B1 (en) | 2017-11-01 |
| EP2854869A4 (en) | 2015-12-30 |
| CA2866896A1 (en) | 2013-11-28 |
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