AU2012337721B2 - Block copolymer having phenylboronic acid group introduced therein, and use thereof - Google Patents
Block copolymer having phenylboronic acid group introduced therein, and use thereof Download PDFInfo
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- AU2012337721B2 AU2012337721B2 AU2012337721A AU2012337721A AU2012337721B2 AU 2012337721 B2 AU2012337721 B2 AU 2012337721B2 AU 2012337721 A AU2012337721 A AU 2012337721A AU 2012337721 A AU2012337721 A AU 2012337721A AU 2012337721 B2 AU2012337721 B2 AU 2012337721B2
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- amino acid
- substituted
- acid
- block copolymer
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- 229920001400 block copolymer Polymers 0.000 title claims abstract description 117
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical group OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 title claims abstract description 31
- 239000002253 acid Substances 0.000 claims abstract description 67
- 125000000539 amino acid group Chemical group 0.000 claims abstract description 67
- 125000002091 cationic group Chemical group 0.000 claims abstract description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 11
- 229920001477 hydrophilic polymer Polymers 0.000 claims abstract description 9
- 125000003277 amino group Chemical group 0.000 claims description 27
- -1 cationic amino acid Chemical class 0.000 claims description 26
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- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 230000002378 acidificating effect Effects 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 125000001165 hydrophobic group Chemical group 0.000 claims description 5
- ZHXTWWCDMUWMDI-UHFFFAOYSA-N dihydroxyboron Chemical compound O[B]O ZHXTWWCDMUWMDI-UHFFFAOYSA-N 0.000 claims description 2
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- 125000002460 pentacosyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002972 pentoses Chemical class 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 239000007981 phosphate-citrate buffer Substances 0.000 description 1
- 239000013612 plasmid Substances 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 108091033319 polynucleotide Proteins 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- IGFXRKMLLMBKSA-UHFFFAOYSA-N purine Chemical compound N1=C[N]C2=NC=NC2=C1 IGFXRKMLLMBKSA-UHFFFAOYSA-N 0.000 description 1
- 108091092562 ribozyme Proteins 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229920002477 rna polymer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000002924 silencing RNA Substances 0.000 description 1
- 239000004055 small Interfering RNA Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229940113082 thymine Drugs 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 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
- A61K47/51—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 non-active ingredient being a modifying agent
- A61K47/62—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 non-active ingredient being a modifying agent the modifying agent being a protein, peptide or polyamino acid
- A61K47/64—Drug-peptide, drug-protein or drug-polyamino acid conjugates, i.e. the modifying agent being a peptide, protein or polyamino acid which is covalently bonded or complexed to a therapeutically active agent
- A61K47/645—Polycationic or polyanionic oligopeptides, polypeptides or polyamino acids, e.g. polylysine, polyarginine, polyglutamic acid or peptide TAT
- A61K47/6455—Polycationic oligopeptides, polypeptides or polyamino acids, e.g. for complexing nucleic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7088—Compounds having three or more nucleosides or nucleotides
- A61K31/713—Double-stranded nucleic acids or oligonucleotides
-
- 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
- A61K47/51—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 non-active ingredient being a modifying agent
- A61K47/56—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 non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
- A61K47/59—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 non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyureas or polyurethanes
- A61K47/60—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 non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyureas or polyurethanes the organic macromolecular compound being a polyoxyalkylene oligomer, polymer or dendrimer, e.g. PEG, PPG, PEO or polyglycerol
-
- 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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/40—Polyamides containing oxygen in the form of ether 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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/42—Polyamides containing atoms other than carbon, hydrogen, oxygen, and nitrogen
-
- 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
-
- 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
- C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G2650/28—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Medicinal Preparation (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Polyamides (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161561022P | 2011-11-17 | 2011-11-17 | |
| US61/561,022 | 2011-11-17 | ||
| PCT/JP2012/079897 WO2013073697A1 (ja) | 2011-11-17 | 2012-11-19 | 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 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2012337721A1 AU2012337721A1 (en) | 2014-05-22 |
| AU2012337721B2 true AU2012337721B2 (en) | 2015-12-10 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2012337721A Ceased AU2012337721B2 (en) | 2011-11-17 | 2012-11-19 | Block copolymer having phenylboronic acid group introduced therein, and use thereof |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US9114177B2 (enExample) |
| EP (1) | EP2781536B1 (enExample) |
| JP (1) | JP5481614B2 (enExample) |
| KR (1) | KR101912978B1 (enExample) |
| CN (1) | CN104093768B (enExample) |
| AU (1) | AU2012337721B2 (enExample) |
| BR (1) | BR112014011831A2 (enExample) |
| CA (1) | CA2853902A1 (enExample) |
| ES (1) | ES2603632T3 (enExample) |
| IN (1) | IN2014CN03580A (enExample) |
| MX (1) | MX2014005540A (enExample) |
| RU (1) | RU2014124333A (enExample) |
| WO (1) | WO2013073697A1 (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9561284B2 (en) | 2011-03-31 | 2017-02-07 | Nanocarrier Co., Ltd. | Pharmaceutical composition containing a block copolymer bound to a boronic acid compound |
| EP2842546A4 (en) | 2012-04-27 | 2015-12-30 | Univ Tokyo | PHARMACEUTICAL COMPOSITION WITH UNIT STRUCTURE FOR NUCLEIC ACID RELIEF |
| US10232054B2 (en) | 2014-02-12 | 2019-03-19 | Accurna, Inc. | Composition for mRNA delivery |
| US10993960B1 (en) * | 2014-05-08 | 2021-05-04 | Kawasaki Institute Of Industrial Promotion | Pharmaceutical composition |
| KR101891655B1 (ko) * | 2016-05-17 | 2018-08-24 | 기초과학연구원 | 페닐보론산이 결합된 고분자를 포함하는 약물 전달체 |
| US10973762B2 (en) | 2016-08-02 | 2021-04-13 | Nippon Kayaku Kabushiki Kaisha | Active-targeting-type polymer derivative, composition containing said polymer derivative, and uses of said polymer derivative and said composition |
| WO2018037996A1 (ja) * | 2016-08-22 | 2018-03-01 | 国立大学法人東京工業大学 | グルタミントランスポーターと多価結合することができるリガンド、及び当該リガンドを含む組成物 |
| CN111050752B (zh) * | 2017-08-31 | 2022-08-16 | 国立大学法人东京大学 | 搭载核酸的单元型聚离子复合物 |
| KR102075476B1 (ko) * | 2017-12-29 | 2020-02-10 | 포항공과대학교 산학협력단 | 페닐보론산이 결합된 고분자를 포함하는 하이드로겔 |
| MX2020011339A (es) | 2018-04-27 | 2021-02-09 | Genedit Inc | Polímero catiónico y uso para suministro de biomolecúla. |
| US12415891B2 (en) | 2018-09-25 | 2025-09-16 | The University Of Tokyo | Amphiphilic poly (amino acid), block copolyer using the amphiphilic poly (amino acid), and complex including the amphiphilic poly (amino acid) or the block copolymer and nucleic acid |
| WO2020241819A1 (ja) | 2019-05-29 | 2020-12-03 | 国立大学法人東京工業大学 | 複合体、医薬、癌治療剤、キット及び結合体 |
| AU2020348451A1 (en) | 2019-09-20 | 2022-04-21 | Glyscend, Inc. | Substituted phenyl boronic acid containing polymers and methods of use |
| EP4306572A4 (en) * | 2021-03-10 | 2025-03-19 | Agc Inc. | POLYMER WITH HALOGEN-CONTAINING SEGMENT AND PHARMACEUTICAL COMPOSITION THEREOF |
| CN114163591B (zh) * | 2021-11-29 | 2023-08-01 | 南方医科大学 | 一种嵌段共聚物、嵌段共聚物载药胶束及其制备方法和应用 |
| CN114533669B (zh) | 2022-01-18 | 2022-11-04 | 武汉大学 | 一种口腔护理组合物及其制备方法和应用 |
| CN114632145B (zh) * | 2022-03-07 | 2024-02-27 | 浙江大学 | 一种负载胰岛素的苯硼酸/脂肪酸双改性ε-聚赖氨酸颗粒及其制备方法 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3257029B2 (ja) * | 1992-04-22 | 2002-02-18 | 日本油脂株式会社 | フェニルボロン酸誘導体及び製造方法 |
| JPH083172A (ja) * | 1994-06-15 | 1996-01-09 | Nippon Oil & Fats Co Ltd | フェニルボロン酸誘導体および製造方法 |
| US6083903A (en) | 1994-10-28 | 2000-07-04 | Leukosite, Inc. | Boronic ester and acid compounds, synthesis and uses |
| JP2002179683A (ja) * | 2000-12-13 | 2002-06-26 | Japan Science & Technology Corp | ポリアミノ酸誘導体から成る核酸関連物質反応試薬 |
| CA2666697C (en) | 2006-10-19 | 2015-03-31 | Nanocarrier Co., Ltd. | Block copolymer for drug conjugates and pharmaceutical composition |
| US20080248097A1 (en) | 2007-02-26 | 2008-10-09 | Kwon Glen S | Polymeric micelles for combination drug delivery |
| JP5737705B2 (ja) | 2008-05-02 | 2015-06-17 | 国立大学法人 筑波大学 | 高分子化環状ニトロキシドラジカル化合物およびその使用 |
| WO2009140421A2 (en) | 2008-05-13 | 2009-11-19 | University Of Washington | Polymeric carrier |
| KR101468268B1 (ko) | 2008-07-29 | 2014-12-02 | 나노캬리아 가부시키가이샤 | 약물 내포 액티브 타겟형 고분자 미셀, 의약 조성물 |
| CN102123698B (zh) | 2008-08-13 | 2016-06-22 | 加利福尼亚技术学院 | 载体纳米颗粒和相关的组合物、方法和系统 |
| WO2010114770A1 (en) | 2009-03-30 | 2010-10-07 | Cerulean Pharma Inc. | Polymer-agent conjugates, particles, compositions, and related methods of use |
| JP5622188B2 (ja) | 2010-01-05 | 2014-11-12 | 独立行政法人物質・材料研究機構 | 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 |
| JP2011173960A (ja) * | 2010-02-23 | 2011-09-08 | Univ Of Tsukuba | 高分子ミセル型光刺激応答性一酸化窒素供与体 |
| US9561284B2 (en) | 2011-03-31 | 2017-02-07 | Nanocarrier Co., Ltd. | Pharmaceutical composition containing a block copolymer bound to a boronic acid compound |
-
2012
- 2012-11-19 AU AU2012337721A patent/AU2012337721B2/en not_active Ceased
- 2012-11-19 WO PCT/JP2012/079897 patent/WO2013073697A1/ja not_active Ceased
- 2012-11-19 BR BR112014011831A patent/BR112014011831A2/pt not_active IP Right Cessation
- 2012-11-19 RU RU2014124333/04A patent/RU2014124333A/ru not_active Application Discontinuation
- 2012-11-19 EP EP12850688.8A patent/EP2781536B1/en not_active Not-in-force
- 2012-11-19 CN CN201280056639.0A patent/CN104093768B/zh not_active Expired - Fee Related
- 2012-11-19 ES ES12850688.8T patent/ES2603632T3/es active Active
- 2012-11-19 IN IN3580CHN2014 patent/IN2014CN03580A/en unknown
- 2012-11-19 US US14/358,816 patent/US9114177B2/en not_active Expired - Fee Related
- 2012-11-19 MX MX2014005540A patent/MX2014005540A/es unknown
- 2012-11-19 KR KR1020147013186A patent/KR101912978B1/ko not_active Expired - Fee Related
- 2012-11-19 CA CA2853902A patent/CA2853902A1/en not_active Abandoned
- 2012-11-19 JP JP2013529476A patent/JP5481614B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| KR20140106511A (ko) | 2014-09-03 |
| KR101912978B1 (ko) | 2018-10-29 |
| EP2781536A1 (en) | 2014-09-24 |
| US20150051347A1 (en) | 2015-02-19 |
| US9114177B2 (en) | 2015-08-25 |
| BR112014011831A2 (pt) | 2017-05-09 |
| WO2013073697A1 (ja) | 2013-05-23 |
| CA2853902A1 (en) | 2013-05-23 |
| CN104093768A (zh) | 2014-10-08 |
| MX2014005540A (es) | 2014-09-22 |
| JPWO2013073697A1 (ja) | 2015-04-02 |
| ES2603632T3 (es) | 2017-02-28 |
| EP2781536A4 (en) | 2015-06-10 |
| CN104093768B (zh) | 2016-09-21 |
| AU2012337721A1 (en) | 2014-05-22 |
| IN2014CN03580A (enExample) | 2015-10-09 |
| EP2781536B1 (en) | 2016-08-17 |
| RU2014124333A (ru) | 2015-12-27 |
| JP5481614B2 (ja) | 2014-04-23 |
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Legal Events
| Date | Code | Title | Description |
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| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |