JP2011140537A - フェニルボロン酸系単量体及びフェニルボロン酸系重合体 - Google Patents
フェニルボロン酸系単量体及びフェニルボロン酸系重合体 Download PDFInfo
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- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 title claims abstract description 136
- 239000000178 monomer Substances 0.000 title claims abstract description 59
- 229920000642 polymer Polymers 0.000 title claims abstract description 19
- YQIGLEFUZMIVHU-UHFFFAOYSA-N 2-methyl-n-propan-2-ylprop-2-enamide Chemical compound CC(C)NC(=O)C(C)=C YQIGLEFUZMIVHU-UHFFFAOYSA-N 0.000 claims description 20
- QNILTEGFHQSKFF-UHFFFAOYSA-N n-propan-2-ylprop-2-enamide Chemical compound CC(C)NC(=O)C=C QNILTEGFHQSKFF-UHFFFAOYSA-N 0.000 claims description 15
- 125000005647 linker group Chemical group 0.000 claims description 12
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 claims description 5
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 13
- 238000003682 fluorination reaction Methods 0.000 abstract description 2
- 239000000499 gel Substances 0.000 description 70
- 230000000052 comparative effect Effects 0.000 description 43
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 40
- 239000008103 glucose Substances 0.000 description 40
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 238000005259 measurement Methods 0.000 description 11
- 239000007864 aqueous solution Substances 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- KNXQDJCZSVHEIW-UHFFFAOYSA-N (3-fluorophenyl)boronic acid Chemical compound OB(O)C1=CC=CC(F)=C1 KNXQDJCZSVHEIW-UHFFFAOYSA-N 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- -1 phenylboronic acid compound Chemical class 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 125000003368 amide group Chemical group 0.000 description 5
- 230000008961 swelling Effects 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 3
- 239000011557 critical solution Substances 0.000 description 3
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical group CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 3
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- HIAJGGCEMFIVBO-UHFFFAOYSA-N 3-carbamoyl-4-methylpent-2-enoic acid Chemical compound CC(C)C(C(N)=O)=CC(O)=O HIAJGGCEMFIVBO-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000036760 body temperature Effects 0.000 description 2
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- XPPWLXNXHSNMKC-UHFFFAOYSA-N phenylboron Chemical compound [B]C1=CC=CC=C1 XPPWLXNXHSNMKC-UHFFFAOYSA-N 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 150000000180 1,2-diols Chemical class 0.000 description 1
- KWNPRVWFJOSGMZ-UHFFFAOYSA-N 2-boronobenzoic acid Chemical compound OB(O)C1=CC=CC=C1C(O)=O KWNPRVWFJOSGMZ-UHFFFAOYSA-N 0.000 description 1
- YNDRELOQYVNSSK-UHFFFAOYSA-N 2-methylprop-2-enamide;phenylboronic acid Chemical compound CC(=C)C(N)=O.OB(O)C1=CC=CC=C1 YNDRELOQYVNSSK-UHFFFAOYSA-N 0.000 description 1
- QGMGHALXLXKCBD-UHFFFAOYSA-N 4-amino-n-(2-aminophenyl)benzamide Chemical compound C1=CC(N)=CC=C1C(=O)NC1=CC=CC=C1N QGMGHALXLXKCBD-UHFFFAOYSA-N 0.000 description 1
- PUMARKJSULLVLY-UHFFFAOYSA-N C(C=C)(=O)NC=1C=C(C(=CC1)C(C(C(F)(F)F)F)(F)F)B(O)O Chemical compound C(C=C)(=O)NC=1C=C(C(=CC1)C(C(C(F)(F)F)F)(F)F)B(O)O PUMARKJSULLVLY-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- RREDGBNKIKPBRK-UHFFFAOYSA-N OB(O)C1=CC=C(C(=O)NCCNC(=O)C=C)C=C1 Chemical compound OB(O)C1=CC=C(C(=O)NCCNC(=O)C=C)C=C1 RREDGBNKIKPBRK-UHFFFAOYSA-N 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 238000003436 Schotten-Baumann reaction Methods 0.000 description 1
- ULVXDHIJOKEBMW-UHFFFAOYSA-N [3-(prop-2-enoylamino)phenyl]boronic acid Chemical compound OB(O)C1=CC=CC(NC(=O)C=C)=C1 ULVXDHIJOKEBMW-UHFFFAOYSA-N 0.000 description 1
- VROCFBAGKYSGGQ-UHFFFAOYSA-N [3-fluoro-4-[2-(prop-2-enoylamino)ethylcarbamoyl]phenyl]boronic acid Chemical compound OB(O)C1=CC=C(C(=O)NCCNC(=O)C=C)C(F)=C1 VROCFBAGKYSGGQ-UHFFFAOYSA-N 0.000 description 1
- 238000002479 acid--base titration Methods 0.000 description 1
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N aminothiocarboxamide Natural products NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229930182830 galactose Natural products 0.000 description 1
- 239000000017 hydrogel Substances 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F220/56—Acrylamide; Methacrylamide
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
【解決手段】フェニルボロン酸系単量体は、一例として一般式(13)で示す構造を有する。
高い親水性を有し、かつフェニル環がフッ素化によりpKaが十分に低く、さらに重合可能な不飽和結合を有する。かくして、このフェニルボロン酸系単量体は、生体レベルであるpKa7.4以下において、高い親水性を有し、多種多様なモノマーと重合することができ、用途に即した重合体を得ることができる。
【選択図】図1
Description
R1で表される2価の連結基としては、カルバモイル結合、アミド結合、アルキル結合、エーテル結合、エステル結合、チオエステル結合、チオエーテル結合、スルホンアミド結合、ウレタン結合、スルホニル結合、イミン結合、ウレア結合、チオウレア結合等のうち少なくとも1又2以上の結合を含む連結基が挙げられる。
また、2価の連結基の一例としてカルバモイル結合を含んだ連結基を適用した場合、上述した一般式(11)は下記一般式(12)で表される(mは0又は1以上の整数である)。
次に、図1に示した合成スキームに従って、本発明のフェニルボロン酸系単量体の一例である4-(2-アクリルアミドエチルカルバモイル)-3-フルオロフェニルボロン酸(以下、これをサンプル1と呼ぶ)を合成した。実際上、この実施例のサンプル1は、以下のようにして合成した。
次に、第1比較例として、図2に示すような一般式(21)で表される3-アクリルアミドフェニルボロン酸(和光純薬、以下、これを比較サンプル1と呼ぶ)を用意した。
次に、第2比較例として、図2に示すような一般式(22)で表される4-(2-アクリルアミドエチルカルバモイル)フェニルボロン酸(以下、これを比較サンプル2と呼ぶ)を用意した。この比較サンプル2は、上記サンプル1で用いたカルボキシフッ素フェニルボロン酸の代わりにカルボキシフェニルボロン酸を出発原料とし、以後、上述したサンプル1と全く同様の操作を行うことで調製した。
次に、上述したサンプル1、比較サンプル1及び比較サンプル2に対し、種々グルコース濃度条件(0g/L、1g/L、3g/L、5g/L、10g/L)において、酸塩基滴定を行うことにより、グルコース濃度と各見かけのpKa変化の関係を導出した。
次に、図3(A)に示すように、N-イソプロピルアクリルアミド(NIPAAm)と、第1比較例である比較サンプル1(AAPBA)とをモル比90/10で調合し、ゲル状のサンプル(以下、これを比較ゲルサンプル1と呼ぶ)を調製した。そして、グルコース濃度を0g/L、5g/Lにそれぞれ調整した各グルコース水溶液に、収縮状態において直径が1mmとなる円柱形状の比較ゲルサンプル1を入れて、5℃〜30℃まで所定温度毎に、各比較ゲルサンプル1の直径変化をそれぞれ計測していった。
次に、ゲルサンプル1に含有させる他のモノマーのモル比を変えたとき、温度変化に応じてゲルサンプル1の直径がどのように変化するかを検証した。なお、図4(A)は、上述した「(5)ゲルサンプルの直径変化と温度との関係」で示した図3(C)のグラフについて、縦軸の直径変化の目盛りを細かく示したグラフである。
次に、図5に示すように、N-イソプロピルメタクリルアミド(NIPMAAm)と、実施例である本発明のフェニルボロン酸系単量体のサンプル1(FPBA)とをモル比92.5/7.5で調合し、ゲル状のサンプル(以下、これをゲルサンプル4と呼ぶ)を生成した。そして、グルコース濃度を0.5g/L、1g/L、3g/L、5g/L、10g/Lにそれぞれ調整した各グルコース水溶液に、収縮状態において直径が1mmとなる円柱形状のゲルサンプル4を入れて、34℃〜45℃まで所定温度毎に、各ゲルサンプル4の膨潤度(d/do)3をそれぞれ測定していった。その結果、図5に示すような計測結果が得られた。また、各グルコース水溶液にゲルサンプル4を入れ、温度が37℃のときの各ゲルサンプル4について、それぞれ光学顕微鏡で撮像したところ、図5に示すように、グルコース濃度が高いほど膨潤することを示す写真が得られた。
Claims (7)
- 下記一般式(1)
で表される
ことを特徴とするフェニルボロン酸系単量体。 - 前記一般式(1)が下記一般式(2)
で表される
ことを特徴とする請求項1記載のフェニルボロン酸系単量体。 - 前記mが1以上である
ことを特徴とする請求項2記載のフェニルボロン酸系単量体。 - 下記一般式(3)
で表される
ことを特徴とするフェニルボロン酸系重合体。 - 前記一般式(3)が下記一般式(4)
で表される
ことを特徴とする請求項4記載のフェニルボロン酸系重合体。 - N-イソプロピルアクリルアミド、N-(ヒドロキシメチル)アクリルアミド及びN-イソプロピルメタクリルアミドのうち少なくともいずれか1つが、請求項1〜3のうちいずれか1項記載のフェニルボロン酸系単量体と重合している
ことを特徴とするフェニルボロン酸系重合体。 - 請求項1〜3のうちいずれか1項記載のフェニルボロン酸系単量体がN-イソプロピルメタクリルアミドと任意の割合で重合することで得られる
ことを特徴とするフェニルボロン酸系重合体。
Priority Applications (4)
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JP2010000821A JP5622188B2 (ja) | 2010-01-05 | 2010-01-05 | フェニルボロン酸系単量体及びフェニルボロン酸系重合体 |
PCT/JP2010/073544 WO2011083711A1 (ja) | 2010-01-05 | 2010-12-27 | フェニルボロン酸系単量体及びフェニルボロン酸系重合体 |
US13/520,710 US20120283403A1 (en) | 2010-01-05 | 2010-12-27 | Phenylboronic Acid Monomer and Phenylboronic Acid Polymer |
EP10842222.1A EP2522679B1 (en) | 2010-01-05 | 2010-12-27 | Phenylboronic acid monomer and phenylboronic acid polymer |
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2013073697A1 (ja) | 2011-11-17 | 2013-05-23 | 国立大学法人 東京大学 | フェニルボロン酸基が導入されたブロックコポリマーおよびその使用 |
US9561284B2 (en) | 2011-03-31 | 2017-02-07 | Nanocarrier Co., Ltd. | Pharmaceutical composition containing a block copolymer bound to a boronic acid compound |
WO2019230961A1 (ja) * | 2018-06-01 | 2019-12-05 | 国立大学法人名古屋大学 | 温度耐性型糖応答性ゲル |
KR20200007374A (ko) * | 2018-07-13 | 2020-01-22 | 주식회사 엔게인 | 수화겔 및 이를 포함하는 글루코스 센서 |
US10993960B1 (en) | 2014-05-08 | 2021-05-04 | Kawasaki Institute Of Industrial Promotion | Pharmaceutical composition |
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JP5696961B2 (ja) * | 2010-05-26 | 2015-04-08 | 独立行政法人物質・材料研究機構 | 糖応答性ゲル及び薬剤投与デバイス |
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US9114177B2 (en) | 2011-11-17 | 2015-08-25 | The University Of Tokyo | Block copolymer having phenylboronic acid group introduced therein, and use thereof |
US10993960B1 (en) | 2014-05-08 | 2021-05-04 | Kawasaki Institute Of Industrial Promotion | Pharmaceutical composition |
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JPWO2019230961A1 (ja) * | 2018-06-01 | 2021-06-10 | 国立大学法人東海国立大学機構 | 温度耐性型糖応答性ゲル |
JP7281659B2 (ja) | 2018-06-01 | 2023-05-26 | 国立大学法人東海国立大学機構 | 温度耐性型糖応答性ゲル |
US11819570B2 (en) | 2018-06-01 | 2023-11-21 | National University Corporation Tokai National Higher Education And Research System | Temperature-resistant sugar-responsive gel |
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KR102098078B1 (ko) | 2018-07-13 | 2020-04-08 | 주식회사 엔게인 | 수화겔 및 이를 포함하는 글루코스 센서 |
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EP2522679A1 (en) | 2012-11-14 |
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US20120283403A1 (en) | 2012-11-08 |
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EP2522679B1 (en) | 2016-07-13 |
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