JP2016515158A5 - - Google Patents
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- Publication number
- JP2016515158A5 JP2016515158A5 JP2016502420A JP2016502420A JP2016515158A5 JP 2016515158 A5 JP2016515158 A5 JP 2016515158A5 JP 2016502420 A JP2016502420 A JP 2016502420A JP 2016502420 A JP2016502420 A JP 2016502420A JP 2016515158 A5 JP2016515158 A5 JP 2016515158A5
- Authority
- JP
- Japan
- Prior art keywords
- hydrogel beads
- beads
- iodinated
- hydrogel
- radiopaque
- 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.)
- Granted
Links
- 239000011324 bead Substances 0.000 claims 53
- 239000000017 hydrogel Substances 0.000 claims 47
- 150000001875 compounds Chemical class 0.000 claims 10
- 239000004372 Polyvinyl alcohol Substances 0.000 claims 7
- 229920002451 polyvinyl alcohol Polymers 0.000 claims 7
- 230000001588 bifunctional effect Effects 0.000 claims 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 6
- 150000001298 alcohols Chemical class 0.000 claims 5
- 238000000034 method Methods 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 229920000642 polymer Polymers 0.000 claims 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 3
- 150000001412 amines Chemical class 0.000 claims 3
- 239000002246 antineoplastic agent Substances 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims 3
- 150000001735 carboxylic acids Chemical class 0.000 claims 3
- 125000000524 functional group Chemical group 0.000 claims 3
- 229910052740 iodine Inorganic materials 0.000 claims 3
- 239000011630 iodine Substances 0.000 claims 3
- ZMZGFLUUZLELNE-UHFFFAOYSA-N 2,3,5-triiodobenzoic acid Chemical compound OC(=O)C1=CC(I)=CC(I)=C1I ZMZGFLUUZLELNE-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 2
- 150000001718 carbodiimides Chemical class 0.000 claims 2
- 229940127089 cytotoxic agent Drugs 0.000 claims 2
- 150000003949 imides Chemical class 0.000 claims 2
- 239000000178 monomer Substances 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- XWAVPOFYNPXXEL-MRVPVSSYSA-N (2r)-2-phenylmethoxypropanoic acid Chemical compound OC(=O)[C@@H](C)OCC1=CC=CC=C1 XWAVPOFYNPXXEL-MRVPVSSYSA-N 0.000 claims 1
- 150000000180 1,2-diols Chemical class 0.000 claims 1
- 150000000185 1,3-diols Chemical class 0.000 claims 1
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical group OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 claims 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical class OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical class OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 1
- 230000003213 activating effect Effects 0.000 claims 1
- 230000004913 activation Effects 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 239000004037 angiogenesis inhibitor Substances 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims 1
- 210000004204 blood vessel Anatomy 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 229940044683 chemotherapy drug Drugs 0.000 claims 1
- 229920001577 copolymer Polymers 0.000 claims 1
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical group N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 claims 1
- 238000006073 displacement reaction Methods 0.000 claims 1
- 229960004679 doxorubicin Drugs 0.000 claims 1
- 230000010102 embolization Effects 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 206010073071 hepatocellular carcinoma Diseases 0.000 claims 1
- 231100000844 hepatocellular carcinoma Toxicity 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- CMMYGCUEJWTBCG-UHFFFAOYSA-N n-(2,2-dimethoxyethyl)prop-2-enamide Chemical compound COC(OC)CNC(=O)C=C CMMYGCUEJWTBCG-UHFFFAOYSA-N 0.000 claims 1
- VOAWOIGCXMLYFY-UHFFFAOYSA-N n-(2-oxoethyl)prop-2-enamide Chemical compound C=CC(=O)NCC=O VOAWOIGCXMLYFY-UHFFFAOYSA-N 0.000 claims 1
- 230000000269 nucleophilic effect Effects 0.000 claims 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 230000002062 proliferating effect Effects 0.000 claims 1
- 230000005855 radiation Effects 0.000 claims 1
- 230000009257 reactivity Effects 0.000 claims 1
- FWFUWXVFYKCSQA-UHFFFAOYSA-M sodium;2-methyl-2-(prop-2-enoylamino)propane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(C)(C)NC(=O)C=C FWFUWXVFYKCSQA-UHFFFAOYSA-M 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361790373P | 2013-03-15 | 2013-03-15 | |
| US61/790,373 | 2013-03-15 | ||
| PCT/US2014/027395 WO2014152488A2 (en) | 2013-03-15 | 2014-03-14 | Imageable embolic microsphere |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018193368A Division JP6723312B2 (ja) | 2013-03-15 | 2018-10-12 | 結像可能な塞栓性微小球 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016515158A JP2016515158A (ja) | 2016-05-26 |
| JP2016515158A5 true JP2016515158A5 (https=) | 2017-04-20 |
| JP6420817B2 JP6420817B2 (ja) | 2018-11-07 |
Family
ID=50631039
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016502420A Active JP6420817B2 (ja) | 2013-03-15 | 2014-03-14 | 結像可能な塞栓性微小球 |
| JP2018193368A Active JP6723312B2 (ja) | 2013-03-15 | 2018-10-12 | 結像可能な塞栓性微小球 |
| JP2020031965A Active JP6983930B2 (ja) | 2013-03-15 | 2020-02-27 | 結像可能な塞栓性微小球 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018193368A Active JP6723312B2 (ja) | 2013-03-15 | 2018-10-12 | 結像可能な塞栓性微小球 |
| JP2020031965A Active JP6983930B2 (ja) | 2013-03-15 | 2020-02-27 | 結像可能な塞栓性微小球 |
Country Status (8)
| Country | Link |
|---|---|
| US (3) | US10307493B2 (https=) |
| EP (1) | EP2968618B1 (https=) |
| JP (3) | JP6420817B2 (https=) |
| KR (1) | KR20160032000A (https=) |
| CN (2) | CN117982687A (https=) |
| CA (1) | CA2906574C (https=) |
| HK (1) | HK1220119A1 (https=) |
| WO (1) | WO2014152488A2 (https=) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2485777B1 (en) | 2009-10-06 | 2013-12-11 | Regents of the University of Minnesota | Bioresorbable embolization microspheres |
| EP3984556B8 (en) | 2012-06-14 | 2025-07-09 | Microvention, Inc. | Polymeric treatment compositions |
| AU2013331439B2 (en) | 2012-10-15 | 2016-05-12 | Microvention, Inc. | Polymeric treatment compositions |
| GB2521997A (en) | 2013-09-06 | 2015-07-15 | Biocompatibles Uk Ltd | Radiopaque polymers |
| GB2519738A (en) * | 2013-09-06 | 2015-05-06 | Biocompatibles Uk Ltd | Radiopaque polymers |
| US10265423B2 (en) | 2015-01-12 | 2019-04-23 | Biosphere Medical, Inc. | Radiopaque monomers, polymers, microspheres, and methods related thereto |
| US20190070332A1 (en) * | 2016-03-14 | 2019-03-07 | Biocompatibles Uk Limited | Oily compositions |
| US10182979B2 (en) | 2016-03-22 | 2019-01-22 | Regents Of The University Of Minnesota | Biodegradable microspheres |
| US10368874B2 (en) | 2016-08-26 | 2019-08-06 | Microvention, Inc. | Embolic compositions |
| CN107050501B (zh) * | 2016-12-29 | 2020-09-15 | 苏州恒瑞迦俐生生物医药科技有限公司 | 一种可视化多羟基聚合体栓塞微球及其制备方法 |
| CN106822983B (zh) * | 2016-12-29 | 2020-09-15 | 苏州恒瑞迦俐生生物医药科技有限公司 | 一种用于微创介入疗法治疗肿瘤疾病的可显影栓塞微球及其制备方法 |
| JP6925014B2 (ja) | 2017-02-15 | 2021-08-25 | ドリームメディカルパートナーズ株式会社 | 塞栓材の製造方法 |
| WO2019074965A1 (en) | 2017-10-09 | 2019-04-18 | Microvention, Inc. | EMBOLIC RADIOACTIVE LIQUID |
| CN107854720B (zh) * | 2017-12-28 | 2020-12-08 | 苏州恒瑞迦俐生生物医药科技有限公司 | 具有造影功能的可载药多羟基聚合物栓塞微球及其制备方法 |
| GB201810788D0 (en) | 2018-06-29 | 2018-08-15 | Biocompatibles Uk Ltd | Biodegradable polymer |
| JP7322073B2 (ja) | 2018-06-29 | 2023-08-07 | バイオコンパティブルズ ユーケー リミテッド | 放射線不透過性ポリマー |
| CN108686259B (zh) * | 2018-07-12 | 2020-11-24 | 中国人民解放军总医院 | 用于血管内栓塞x线下可显影的载药微球及其制备方法 |
| TW202031299A (zh) * | 2018-11-13 | 2020-09-01 | 大陸商上海盛迪醫藥有限公司 | 一種聚合物及其組合物 |
| CN110628008B (zh) * | 2019-06-25 | 2021-10-08 | 复旦大学 | 一种具有x-射线显影功能的含碘聚碳酸酯及其制备方法与应用 |
| GB201910286D0 (en) | 2019-07-18 | 2019-09-04 | Biocompatibles Uk Ltd | Radiopaque polymers |
| EP4026859A4 (en) * | 2019-09-05 | 2022-12-28 | Dalian Heyuan Medical Equipments Co., Ltd. | Poly[alpha-cyanoacrylate] hydrolyzate and preparation method and applicaiton thereof |
| CN112972754B (zh) * | 2021-02-24 | 2022-07-19 | 苏州微尺度科技有限公司 | 一种可视化岩藻多糖栓塞微球及其制备方法 |
| US20230037198A1 (en) * | 2021-07-29 | 2023-02-02 | Varian Medical Systems, Inc. | Apparatuses and methods for producing embolic particles with activated loading sites |
| CN118743779A (zh) * | 2021-11-12 | 2024-10-08 | 重庆百迈腾世医药科技有限公司 | 基于活性金属微球的复合栓塞剂、制备方法及其应用 |
| CN114057600B (zh) * | 2021-12-02 | 2024-02-02 | 上海汇禾医疗科技股份有限公司 | 一种可x射线显影分子、载药栓塞微球及其制备方法 |
| CN114344554A (zh) * | 2022-02-11 | 2022-04-15 | 上海益思妙医疗器械有限公司 | 一种peg化合物作为制备栓塞剂的应用 |
| CN116059368B (zh) * | 2022-07-20 | 2025-07-25 | 暨南大学 | Smo抑制剂在制备预防、延缓或减轻动静脉内瘘通路狭窄的药物中的应用 |
| EP4563569A1 (en) | 2022-08-25 | 2025-06-04 | Cardiolink Science (Shenzhen) Medical Technology Development Co., Ltd. | Amide compound containing iodo aryl or iodo heteroaryl, and preparation method therefor and use thereof |
| CN116574060A (zh) * | 2022-09-19 | 2023-08-11 | 科睿驰(深圳)医疗科技发展有限公司 | X射线显影化合物及其制备方法、x射线显影栓塞材料及其制备方法 |
| CN117323294B (zh) * | 2023-09-25 | 2024-05-31 | 至微(深圳)医学科技有限公司 | 一种载药栓塞微球及其制备方法和应用 |
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| US2860986A (en) | 1956-08-31 | 1958-11-18 | Eastman Kodak Co | Partially acetalized polyvinyl alcohol containing active halogen |
| US3840482A (en) | 1971-09-13 | 1974-10-08 | Ici Australia Ltd | Process for curing poly(vinyl alcohol)matrix beads |
| US4406878A (en) | 1978-08-02 | 1983-09-27 | Eastman Kodak Company | Iodinated contrast agent for radiography |
| US4306031A (en) | 1979-08-14 | 1981-12-15 | Mitsubishi Chemical Industries Limited | Weakly acidic cation exchange resin and process for producing same |
| US5141739A (en) * | 1986-07-03 | 1992-08-25 | Advanced Magnetics, Inc. | Delivery of x-ray contrast agents using receptor mediated endocytosis |
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| EP0391741B1 (en) | 1989-04-06 | 1995-04-19 | Merocel Corporation | Polymeric broad-spectrum antimicrobial materials |
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| JPH0656676A (ja) | 1992-08-05 | 1994-03-01 | Hori Shinichi | 血管塞栓用懸濁液 |
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| TW272976B (https=) * | 1993-08-06 | 1996-03-21 | Ciba Geigy Ag | |
| AU4566001A (en) | 2000-03-13 | 2001-09-24 | Biocure Inc | Embolic compositions |
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| CA2431662A1 (en) * | 2000-12-31 | 2002-07-11 | Amersham Biosciences Ab | A method for the manufacture of compositions containing low concentrations of salts |
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| US20060292077A1 (en) * | 2005-03-18 | 2006-12-28 | Zhao Jonathon Z | Dendritic and star-shaped contrast agents for medical devices and bioabsorbable radiopaque bulk material and method for producing same |
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| ITRM20080636A1 (it) * | 2008-11-28 | 2010-05-29 | Univ Palermo | Procedimento per la produzione di derivati funzionalizzati dell acido ialuronico e relativi idrogeli. |
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| EP2365009A1 (en) * | 2010-03-10 | 2011-09-14 | Universite Claude Bernard Lyon 1 (UCBL) | Radiopaque, non-biodegradable, water-insoluble iodinated benzyl ethers of poly(vinyl alcohol), preparation method thereof, injectable embolizing compositions containing thereof and use thereof |
| ES2368307B1 (es) | 2010-04-28 | 2012-10-17 | Universidade De Santiago De Compostela | Hidrogeles elaborados a base de polímeros aniónicos de origen natural. |
| KR20130124322A (ko) | 2010-09-29 | 2013-11-13 | 사이언 카디오-바스큘라, 인크. | 미소구의 가공 방법, 이에 의해 가공된 미소구, 및 그의 용도 |
| CN103249436B (zh) * | 2010-12-09 | 2015-09-30 | 东丽株式会社 | 生物降解性颗粒、血管栓塞材料及生物降解性颗粒的制造方法 |
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| JP6506230B2 (ja) | 2016-09-28 | 2019-04-24 | Necプラットフォームズ株式会社 | 音声無音検知装置、音声無音検知方法、音声無音検知プログラム、及び音声無音検知システム |
-
2014
- 2014-03-14 HK HK16108169.0A patent/HK1220119A1/zh unknown
- 2014-03-14 CN CN202311346292.XA patent/CN117982687A/zh active Pending
- 2014-03-14 WO PCT/US2014/027395 patent/WO2014152488A2/en not_active Ceased
- 2014-03-14 CA CA2906574A patent/CA2906574C/en active Active
- 2014-03-14 JP JP2016502420A patent/JP6420817B2/ja active Active
- 2014-03-14 CN CN201480024766.1A patent/CN105517580A/zh active Pending
- 2014-03-14 KR KR1020157028536A patent/KR20160032000A/ko not_active Ceased
- 2014-03-14 US US14/777,168 patent/US10307493B2/en active Active
- 2014-03-14 EP EP14721095.9A patent/EP2968618B1/en active Active
-
2018
- 2018-10-12 JP JP2018193368A patent/JP6723312B2/ja active Active
-
2019
- 2019-04-11 US US16/381,204 patent/US20190328908A1/en not_active Abandoned
-
2020
- 2020-01-22 US US16/749,370 patent/US11672876B2/en active Active
- 2020-02-27 JP JP2020031965A patent/JP6983930B2/ja active Active
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