CA3005306C - Biodegradable block polyurethane copolymers comprising folic acid and their use in medical devices - Google Patents
Biodegradable block polyurethane copolymers comprising folic acid and their use in medical devices Download PDFInfo
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- CA3005306C CA3005306C CA3005306A CA3005306A CA3005306C CA 3005306 C CA3005306 C CA 3005306C CA 3005306 A CA3005306 A CA 3005306A CA 3005306 A CA3005306 A CA 3005306A CA 3005306 C CA3005306 C CA 3005306C
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- Prior art keywords
- block copolymer
- ch2ch3
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- monomers
- medical device
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- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 title claims abstract description 146
- 235000019152 folic acid Nutrition 0.000 title claims abstract description 90
- 239000011724 folic acid Substances 0.000 title claims abstract description 90
- 239000004814 polyurethane Substances 0.000 title claims abstract description 70
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 66
- OVBPIULPVIDEAO-UHFFFAOYSA-N N-Pteroyl-L-glutaminsaeure Natural products C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-UHFFFAOYSA-N 0.000 title claims abstract description 58
- 229960000304 folic acid Drugs 0.000 title claims abstract description 58
- 210000005036 nerve Anatomy 0.000 claims abstract description 110
- -1 citrate ester Chemical class 0.000 claims abstract description 105
- 230000012010 growth Effects 0.000 claims abstract description 34
- 208000027418 Wounds and injury Diseases 0.000 claims abstract description 27
- 229920002988 biodegradable polymer Polymers 0.000 claims abstract description 18
- 239000004621 biodegradable polymer Substances 0.000 claims abstract description 18
- 229920001577 copolymer Polymers 0.000 claims abstract description 10
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 106
- 229920001400 block copolymer Polymers 0.000 claims description 92
- 229920001223 polyethylene glycol Polymers 0.000 claims description 71
- 239000000178 monomer Substances 0.000 claims description 69
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 50
- 229920000642 polymer Polymers 0.000 claims description 48
- 229920000728 polyester Polymers 0.000 claims description 44
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 36
- 230000008439 repair process Effects 0.000 claims description 33
- 229920005862 polyol Polymers 0.000 claims description 22
- 150000003077 polyols Chemical class 0.000 claims description 22
- 229920001610 polycaprolactone Polymers 0.000 claims description 21
- 239000004632 polycaprolactone Substances 0.000 claims description 20
- 239000007795 chemical reaction product Substances 0.000 claims description 19
- 239000000463 material Substances 0.000 claims description 17
- 150000002148 esters Chemical class 0.000 claims description 15
- 150000001345 alkine derivatives Chemical group 0.000 claims description 14
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims description 14
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 14
- 206010052428 Wound Diseases 0.000 claims description 13
- 230000015556 catabolic process Effects 0.000 claims description 12
- 239000000306 component Substances 0.000 claims description 12
- 238000006731 degradation reaction Methods 0.000 claims description 12
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims description 12
- 229920000747 poly(lactic acid) Polymers 0.000 claims description 12
- 210000001428 peripheral nervous system Anatomy 0.000 claims description 11
- 150000001413 amino acids Chemical class 0.000 claims description 10
- 150000001540 azides Chemical class 0.000 claims description 9
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 229920003232 aliphatic polyester Polymers 0.000 claims description 8
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 claims description 8
- 235000001014 amino acid Nutrition 0.000 claims description 7
- 150000001768 cations Chemical class 0.000 claims description 7
- 125000005442 diisocyanate group Chemical group 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- DZAUWHJDUNRCTF-UHFFFAOYSA-N 3-(3,4-dihydroxyphenyl)propanoic acid Chemical compound OC(=O)CCC1=CC=C(O)C(O)=C1 DZAUWHJDUNRCTF-UHFFFAOYSA-N 0.000 claims description 6
- 229920000331 Polyhydroxybutyrate Polymers 0.000 claims description 6
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 claims description 6
- 235000008206 alpha-amino acids Nutrition 0.000 claims description 6
- 229960003638 dopamine Drugs 0.000 claims description 6
- 238000001727 in vivo Methods 0.000 claims description 6
- 239000005014 poly(hydroxyalkanoate) Substances 0.000 claims description 6
- 239000005015 poly(hydroxybutyrate) Substances 0.000 claims description 6
- 229920001451 polypropylene glycol Polymers 0.000 claims description 6
- 210000000457 tarsus Anatomy 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 230000007423 decrease Effects 0.000 claims description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 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
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 125000003929 folic acid group Chemical group 0.000 claims description 4
- 150000003141 primary amines Chemical group 0.000 claims description 4
- 125000006755 (C2-C20) alkyl group Chemical group 0.000 claims description 3
- ZLYYJUJDFKGVKB-OWOJBTEDSA-N (e)-but-2-enedioyl dichloride Chemical compound ClC(=O)\C=C\C(Cl)=O ZLYYJUJDFKGVKB-OWOJBTEDSA-N 0.000 claims description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 3
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 claims description 3
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 claims description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 3
- 125000004450 alkenylene group Chemical group 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000000732 arylene group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 239000008358 core component Substances 0.000 claims description 3
- 239000011258 core-shell material Substances 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 3
- 239000011976 maleic acid Substances 0.000 claims description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 3
- WTDRDQBEARUVNC-ZCFIWIBFSA-N D-DOPA Chemical compound OC(=O)[C@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-ZCFIWIBFSA-N 0.000 claims description 2
- 208000001738 Nervous System Trauma Diseases 0.000 claims description 2
- 239000001530 fumaric acid Substances 0.000 claims description 2
- 125000005549 heteroarylene group Chemical group 0.000 claims description 2
- 229920001477 hydrophilic polymer Polymers 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
- 208000028412 nervous system injury Diseases 0.000 claims description 2
- 230000006378 damage Effects 0.000 abstract description 15
- 208000014674 injury Diseases 0.000 abstract description 15
- 208000017787 Paraneoplastic neurologic syndrome Diseases 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 42
- 229940014144 folate Drugs 0.000 description 32
- 238000003786 synthesis reaction Methods 0.000 description 31
- 230000015572 biosynthetic process Effects 0.000 description 28
- 210000004027 cell Anatomy 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 101000916485 Homo sapiens Chondroitin sulfate proteoglycan 5 Proteins 0.000 description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- 239000000047 product Substances 0.000 description 22
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 17
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- 239000000227 bioadhesive Substances 0.000 description 9
- 239000012620 biological material Substances 0.000 description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
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- 229920001440 poly(ε-caprolactone)-block-poly(ethylene glycol) Polymers 0.000 description 5
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 4
- 230000021699 Schwann cell migration Effects 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 238000012650 click reaction Methods 0.000 description 4
- 238000013461 design Methods 0.000 description 4
- JQZRVMZHTADUSY-UHFFFAOYSA-L di(octanoyloxy)tin Chemical compound [Sn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O JQZRVMZHTADUSY-UHFFFAOYSA-L 0.000 description 4
- 229910001873 dinitrogen Inorganic materials 0.000 description 4
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- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
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- 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
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| CN109646159B (zh) * | 2018-12-26 | 2021-02-05 | 上海纳米技术及应用国家工程研究中心有限公司 | 解剖型3d打印波纹管弹性体气管支架的制备方法及产品 |
| CN109777090B (zh) * | 2019-01-11 | 2021-02-19 | 齐鲁工业大学 | 一种有机聚合物/二氧化硅复合纳米膜及其制备方法 |
| CN109971163B (zh) * | 2019-04-04 | 2021-02-02 | 陕西科技大学 | 一种水性聚氨酯/Fe3+凝胶材料的制备方法 |
| US20230087713A1 (en) * | 2019-12-24 | 2023-03-23 | The Penn State Research Foundation | Bioadhesive compositions and methods of making the same |
| WO2021207331A1 (en) * | 2020-04-07 | 2021-10-14 | The Penn State Research Foundation | Biodegradable and multifunctional neural block devices |
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| KR102553303B1 (ko) * | 2020-07-08 | 2023-07-07 | 주식회사 아이센스 | 관능화된 열가소성 폴리우레탄, 이의 제조방법 및 이를 이용한 의료용 고기능성 복합재료의 제조 방법 및 이를 포함하는 의료장치 |
| CN112029068B (zh) * | 2020-09-08 | 2022-05-31 | 浙江德普斯医疗科技股份有限公司 | 聚氨酯化合物及其制备方法以及生物粘结剂 |
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| CN112940218B (zh) * | 2021-02-04 | 2022-11-01 | 四川大学 | 可降解的电活性聚氨酯材料及其制备方法和应用 |
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| EP2634179A1 (en) | 2012-02-28 | 2013-09-04 | Sanofi | Functional PLA-PEG copolymers, the nanoparticles thereof, their preparation and use for targeted drug delivery and imaging |
| CA2896587C (en) * | 2013-01-04 | 2019-02-05 | Board Of Regents, The University Of Texas System | Compositions comprising citrate and applications thereof |
| ES2922848T3 (es) * | 2013-09-05 | 2022-09-20 | Penn State Res Found | Bioelastómeros y aplicaciones de los mismos |
| CN103751148B (zh) * | 2014-01-10 | 2017-08-25 | 华南理工大学 | 一种以双亲性聚氨酯为载体的具有靶向和缓释作用的抗肿瘤药物纳米微球及其制备方法 |
| EP3119407A4 (en) * | 2014-03-17 | 2017-03-29 | The Penn State Research Foundation | Methods of promoting bone growth and healing |
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2016
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- 2016-11-29 US US15/779,623 patent/US11267965B2/en active Active
- 2016-11-29 CN CN201680069935.2A patent/CN108472120B/zh active Active
- 2016-11-29 JP JP2018547859A patent/JP7090027B2/ja active Active
- 2016-11-29 WO PCT/US2016/064018 patent/WO2017095816A1/en not_active Ceased
- 2016-11-29 EP EP16871362.6A patent/EP3383315B1/en active Active
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|---|---|
| CN108472120A (zh) | 2018-08-31 |
| JP7090027B2 (ja) | 2022-06-23 |
| EP3383315A1 (en) | 2018-10-10 |
| EP3383315B1 (en) | 2023-09-27 |
| CN108472120B (zh) | 2022-02-25 |
| US11267965B2 (en) | 2022-03-08 |
| US20180340063A1 (en) | 2018-11-29 |
| JP2019504922A (ja) | 2019-02-21 |
| EP3383315A4 (en) | 2019-06-19 |
| CA3005306A1 (en) | 2017-06-08 |
| WO2017095816A1 (en) | 2017-06-08 |
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