JP2012503603A5 - - Google Patents
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- JP2012503603A5 JP2012503603A5 JP2011528068A JP2011528068A JP2012503603A5 JP 2012503603 A5 JP2012503603 A5 JP 2012503603A5 JP 2011528068 A JP2011528068 A JP 2011528068A JP 2011528068 A JP2011528068 A JP 2011528068A JP 2012503603 A5 JP2012503603 A5 JP 2012503603A5
- Authority
- JP
- Japan
- Prior art keywords
- acid
- nanocarrier
- group
- peg
- formula
- 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
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- 239000002539 nanocarrier Substances 0.000 claims description 56
- 239000002202 Polyethylene glycol Substances 0.000 claims description 45
- 229920001223 polyethylene glycol Polymers 0.000 claims description 45
- 239000000178 monomer Substances 0.000 claims description 30
- 229940079593 drug Drugs 0.000 claims description 24
- 239000003814 drug Substances 0.000 claims description 24
- 229920000642 polymer Polymers 0.000 claims description 23
- KDXKERNSBIXSRK-UHFFFAOYSA-N lysine Chemical compound NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 18
- 239000002184 metal Substances 0.000 claims description 16
- 230000003287 optical effect Effects 0.000 claims description 16
- 239000000523 sample Substances 0.000 claims description 16
- BHQCQFFYRZLCQQ-UHFFFAOYSA-N (3alpha,5alpha,7alpha,12alpha)-3,7,12-trihydroxy-cholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 BHQCQFFYRZLCQQ-UHFFFAOYSA-N 0.000 claims description 15
- KXGVEGMKQFWNSR-UHFFFAOYSA-N deoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 KXGVEGMKQFWNSR-UHFFFAOYSA-N 0.000 claims description 15
- 230000005298 paramagnetic effect Effects 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 15
- 239000004472 Lysine Substances 0.000 claims description 14
- 239000004380 Cholic acid Substances 0.000 claims description 13
- BHQCQFFYRZLCQQ-OELDTZBJSA-N cholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 BHQCQFFYRZLCQQ-OELDTZBJSA-N 0.000 claims description 13
- 229960002471 cholic acid Drugs 0.000 claims description 13
- 235000019416 cholic acid Nutrition 0.000 claims description 13
- 125000003716 cholic acid group Chemical group 0.000 claims description 13
- 239000013522 chelant Substances 0.000 claims description 10
- 230000002209 hydrophobic effect Effects 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 7
- AHLPHDHHMVZTML-UHFFFAOYSA-N Ornithine Chemical compound NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 claims description 6
- 239000012216 imaging agent Substances 0.000 claims description 6
- 239000003446 ligand Substances 0.000 claims description 6
- IVHKZGYFKJRXBD-UHFFFAOYSA-N amino carbamate Chemical compound NOC(N)=O IVHKZGYFKJRXBD-UHFFFAOYSA-N 0.000 claims description 5
- 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 claims description 5
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims description 4
- OGNSCSPNOLGXSM-UHFFFAOYSA-N 2,4-diaminobutyric acid Chemical compound NCCC(N)C(O)=O OGNSCSPNOLGXSM-UHFFFAOYSA-N 0.000 claims description 4
- PECYZEOJVXMISF-UHFFFAOYSA-N 3-aminoalanine Chemical compound [NH3+]CC(N)C([O-])=O PECYZEOJVXMISF-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims description 4
- MMCOUVMKNAHQOY-UHFFFAOYSA-N carbonoperoxoic acid Chemical compound OOC(O)=O MMCOUVMKNAHQOY-UHFFFAOYSA-N 0.000 claims description 4
- 125000006850 spacer group Chemical group 0.000 claims description 4
- DRAJWRKLRBNJRQ-UHFFFAOYSA-N Hydroxycarbamic acid Chemical compound ONC(O)=O DRAJWRKLRBNJRQ-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 230000005661 hydrophobic surface Effects 0.000 claims description 3
- 238000003384 imaging method Methods 0.000 claims description 3
- JDPJOMBMWZQSCY-BYPYZUCNSA-N (2r)-2-(2-aminoethylamino)-3-sulfanylpropanoic acid Chemical compound NCCN[C@@H](CS)C(O)=O JDPJOMBMWZQSCY-BYPYZUCNSA-N 0.000 claims description 2
- RUDATBOHQWOJDD-UHFFFAOYSA-N (3beta,5beta,7alpha)-3,7-Dihydroxycholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)CC2 RUDATBOHQWOJDD-UHFFFAOYSA-N 0.000 claims description 2
- RBNPOMFGQQGHHO-UHFFFAOYSA-N -2,3-Dihydroxypropanoic acid Natural products OCC(O)C(O)=O RBNPOMFGQQGHHO-UHFFFAOYSA-N 0.000 claims description 2
- UKAUYVFTDYCKQA-UHFFFAOYSA-N -2-Amino-4-hydroxybutanoic acid Natural products OC(=O)C(N)CCO UKAUYVFTDYCKQA-UHFFFAOYSA-N 0.000 claims description 2
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 claims description 2
- JVYDLYGCSIHCMR-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)butanoic acid Chemical compound CCC(CO)(CO)C(O)=O JVYDLYGCSIHCMR-UHFFFAOYSA-N 0.000 claims description 2
- UFYGCFHQAXXBCF-UHFFFAOYSA-N 2,4-dihydroxybutanoic acid Chemical compound OCCC(O)C(O)=O UFYGCFHQAXXBCF-UHFFFAOYSA-N 0.000 claims description 2
- YSHBXOGJSHJCAO-UHFFFAOYSA-N 3-amino-2-(aminomethyl)-2-methylpropanoic acid Chemical compound NCC(C)(CN)C(O)=O YSHBXOGJSHJCAO-UHFFFAOYSA-N 0.000 claims description 2
- IPHWMPQMASHHHM-UHFFFAOYSA-N 3-amino-2-(aminomethyl)propanoic acid Chemical compound NCC(CN)C(O)=O IPHWMPQMASHHHM-UHFFFAOYSA-N 0.000 claims description 2
- ZUZXRORWWYAGIY-PGHAKIONSA-N 3alpha,12alpha,16alpha-Trihydroxy-5beta-cholan-24-oic Acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@@H](O)[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 ZUZXRORWWYAGIY-PGHAKIONSA-N 0.000 claims description 2
- ZEDMWCZZMFUPFY-UHFFFAOYSA-N 4-amino-2-(2-aminoethyl)butanoic acid Chemical compound NCCC(C(O)=O)CCN ZEDMWCZZMFUPFY-UHFFFAOYSA-N 0.000 claims description 2
- RNQFIALWYREPBF-UHFFFAOYSA-N 5-amino-2-propylpentanoic acid Chemical group CCCC(C(O)=O)CCCN RNQFIALWYREPBF-UHFFFAOYSA-N 0.000 claims description 2
- FJHBVJOVLFPMQE-QFIPXVFZSA-N 7-Ethyl-10-Hydroxy-Camptothecin Chemical compound C1=C(O)C=C2C(CC)=C(CN3C(C4=C([C@@](C(=O)OC4)(O)CC)C=C33)=O)C3=NC2=C1 FJHBVJOVLFPMQE-QFIPXVFZSA-N 0.000 claims description 2
- KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 claims description 2
- RBNPOMFGQQGHHO-UWTATZPHSA-N D-glyceric acid Chemical compound OC[C@@H](O)C(O)=O RBNPOMFGQQGHHO-UWTATZPHSA-N 0.000 claims description 2
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 claims description 2
- UKAUYVFTDYCKQA-VKHMYHEASA-N L-homoserine Chemical compound OC(=O)[C@@H](N)CCO UKAUYVFTDYCKQA-VKHMYHEASA-N 0.000 claims description 2
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 claims description 2
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 claims description 2
- 229930012538 Paclitaxel Natural products 0.000 claims description 2
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 claims description 2
- 239000004473 Threonine Substances 0.000 claims description 2
- BHQCQFFYRZLCQQ-PGHAKIONSA-N allocholic acid Chemical compound C([C@@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 BHQCQFFYRZLCQQ-PGHAKIONSA-N 0.000 claims description 2
- 239000003125 aqueous solvent Substances 0.000 claims description 2
- VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical compound C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 claims description 2
- 229940127093 camptothecin Drugs 0.000 claims description 2
- RUDATBOHQWOJDD-BSWAIDMHSA-N chenodeoxycholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 RUDATBOHQWOJDD-BSWAIDMHSA-N 0.000 claims description 2
- 229960001091 chenodeoxycholic acid Drugs 0.000 claims description 2
- KXGVEGMKQFWNSR-LLQZFEROSA-N deoxycholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 KXGVEGMKQFWNSR-LLQZFEROSA-N 0.000 claims description 2
- 229960003964 deoxycholic acid Drugs 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
- VSJKWCGYPAHWDS-UHFFFAOYSA-N dl-camptothecin Natural products C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-UHFFFAOYSA-N 0.000 claims description 2
- 229960004679 doxorubicin Drugs 0.000 claims description 2
- VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 claims description 2
- 229960005420 etoposide Drugs 0.000 claims description 2
- 229960003104 ornithine Drugs 0.000 claims description 2
- 229960001592 paclitaxel Drugs 0.000 claims description 2
- ZUZXRORWWYAGIY-UHFFFAOYSA-N phytocholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CC(O)C(C(CCC(O)=O)C)C1(C)C(O)C2 ZUZXRORWWYAGIY-UHFFFAOYSA-N 0.000 claims description 2
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims description 2
- -1 Hydroxylamino Chemical group 0.000 claims 1
- 239000002907 paramagnetic material Substances 0.000 claims 1
- 238000000034 method Methods 0.000 description 4
- 150000001413 amino acids Chemical class 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9927208P | 2008-09-23 | 2008-09-23 | |
| US61/099,272 | 2008-09-23 | ||
| PCT/US2009/057852 WO2010039496A2 (en) | 2008-09-23 | 2009-09-22 | Nanocarriers for drug delivery |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012503603A JP2012503603A (ja) | 2012-02-09 |
| JP2012503603A5 true JP2012503603A5 (OSRAM) | 2012-11-08 |
| JP5539993B2 JP5539993B2 (ja) | 2014-07-02 |
Family
ID=41508806
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011528068A Active JP5539993B2 (ja) | 2008-09-23 | 2009-09-22 | 薬物送達のためのナノ担体 |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US9579400B2 (OSRAM) |
| EP (1) | EP2344134B1 (OSRAM) |
| JP (1) | JP5539993B2 (OSRAM) |
| CN (1) | CN102159189B (OSRAM) |
| WO (1) | WO2010039496A2 (OSRAM) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090136937A1 (en) | 2007-05-09 | 2009-05-28 | Coleman Matthew A | Methods and systems for monitoring production of a target protein in a nanolipoprotein particle |
| US10106650B2 (en) | 2011-05-13 | 2018-10-23 | The Regents Of The University Of California | Reversibly crosslinked micelle systems |
| EP3473273A1 (en) | 2011-07-29 | 2019-04-24 | Avelas Biosciences, Inc. | Selective delivery molecules and methods of use |
| US9644038B2 (en) | 2011-12-21 | 2017-05-09 | The Regents Of The University Of California | Apolipoprotein nanodiscs with telodendrimer |
| US8895055B2 (en) * | 2011-12-21 | 2014-11-25 | The Regents Of The University Of California | Telodendrimer nanodiscs without apolipoprotein |
| US10406233B2 (en) * | 2011-12-21 | 2019-09-10 | The Regents Of The University Of California | Telodendrimers with enhanced drug delivery |
| CA2873572C (en) * | 2012-05-16 | 2021-07-06 | Mewa Singh | Pharmaceutical compositions for the delivery of substantially water-insoluble drugs |
| US9642916B2 (en) * | 2012-12-12 | 2017-05-09 | The Regents Of The University Of California | Porphyrin modified telodendrimers |
| HK1217720A1 (zh) | 2013-01-30 | 2017-01-20 | Avelas Acquisition Corporation | 选择性递送分子及使用方法 |
| US11406714B2 (en) | 2013-08-21 | 2022-08-09 | The Research Foundation For The State University Of New York | Telodendrimers and nanocarriers and methods of using same |
| EP3204048A4 (en) | 2014-10-07 | 2018-06-27 | The Research Foundation for the State University of New York | Functional segregated telodendrimers and nanocarriers and methods of making and using same |
| WO2016168607A1 (en) * | 2015-04-15 | 2016-10-20 | University Of Tennessee Research Foundation | Compositions and methods of muc13 antibodies for cancer treatment and diagnosis |
| TWI614023B (zh) * | 2015-05-20 | 2018-02-11 | 免疫功坊股份有限公司 | 具有標的部分及效應部分的胜肽核多臂接合物 |
| KR102081192B1 (ko) * | 2015-07-20 | 2020-02-25 | 에스티팜 주식회사 | 경구투여가 어려운 약물의 경구투여를 위한 신규한 약물 전달체 및 이의 제조방법 |
| US12226529B2 (en) | 2015-08-25 | 2025-02-18 | Lawrence Livermore National Security, Llc | Stable nanolipoprotein particles and related compositions methods and systems |
| JP2018527350A (ja) * | 2015-09-01 | 2018-09-20 | イミュンワーク インク．Ｉｍｍｕｎｗｏｒｋ Ｉｎｃ． | 血餅形成の予防及び／又は血栓症の治療のための分子構築物 |
| US11279749B2 (en) | 2015-09-11 | 2022-03-22 | Lawrence Livermore National Security, Llc | Synthetic apolipoproteins, and related compositions methods and systems for nanolipoprotein particles formation |
| CN108601949A (zh) * | 2016-01-14 | 2018-09-28 | 加利福尼亚大学董事会 | 用llp2a-二膦酸盐化合物治疗骨坏死的方法 |
| CN110392583B (zh) * | 2016-09-15 | 2023-01-03 | 加利福尼亚大学董事会 | 改进的杂化的末端树枝状聚合物 |
| CN108159422B (zh) * | 2016-12-07 | 2020-09-15 | 上海时莱生物技术有限公司 | 一种自组装载药系统及其复合制剂的制备方法 |
| WO2018136778A1 (en) | 2017-01-19 | 2018-07-26 | The Research Foundation For The State University Of New York | Telodendrimers with riboflavin moieties and nanocarriers and methods of making and using same |
| WO2018160759A1 (en) * | 2017-02-28 | 2018-09-07 | The Research Foundation For The State University Of New York | Zwitterionic dendritic amphiphiles, zwitterionic dendrimers, zwitterionic telodendrimers, nanocarriers comprising same, and methods of making and using same |
| WO2018204421A2 (en) | 2017-05-02 | 2018-11-08 | Lawrence Livermore National Security, Llc | Momp telonanoparticles, and related compositions, methods and systems |
| WO2018204495A1 (en) | 2017-05-02 | 2018-11-08 | Synthetic Genomics, Inc. | Nanolipoprotein particles and related compositions methods and systems for loading rna |
| WO2019079277A1 (en) * | 2017-10-16 | 2019-04-25 | Dynamic Biologics Inc. | POLYMERIC COMPOSITIONS OF MONOMETHYL FUMARATE FOR THE TREATMENT OF RECURRENT-REMEDY PLAQUE SCLEROSIS AND PSORIASIS |
| CN107955153B (zh) * | 2017-11-29 | 2020-12-15 | 南京拉克森生物医药科技有限公司 | 一种聚乙二醇-去氧胆酸及其衍生物的制备方法和应用 |
| CA3150959A1 (en) * | 2019-08-14 | 2021-02-18 | The Regents Of The University Of California | Smart peptides and transformable nanoparticles for cancer immunotherapy |
| CA3164919A1 (en) * | 2019-12-17 | 2021-06-24 | The Regents Of The University Of California | Sequential targeting in crosslinking nano-theranostics for treating brain tumors |
| CN111189747B (zh) * | 2020-01-05 | 2022-03-29 | 天津大学 | 一种针对颗粒聚结成球技术的三元溶剂体系筛选方法 |
| KR20210122492A (ko) * | 2020-04-01 | 2021-10-12 | 에스티팜 주식회사 | 항암 요법을 위한 헤파린-담즙산 올리고머 컨쥬게이트 |
| CN112679504B (zh) * | 2020-12-24 | 2022-04-19 | 河北工业大学 | 两亲性共轭寡聚物及其制备及利用其自组装制备得到的载药纳米粒子 |
| CN119661825B (zh) * | 2023-09-19 | 2025-11-14 | 上海交通大学 | 聚两性离子-胆酸及其合成以及其在药物递送中的应用 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL139541A0 (en) * | 1998-05-20 | 2004-02-08 | Liposome Co Inc | Novel particulate formulations |
| US6365191B1 (en) * | 1999-02-17 | 2002-04-02 | Dabur Research Foundation | Formulations of paclitaxel, its derivatives or its analogs entrapped into nanoparticles of polymeric micelles, process for preparing same and the use thereof |
| US20020041898A1 (en) | 2000-01-05 | 2002-04-11 | Unger Evan C. | Novel targeted delivery systems for bioactive agents |
| AU2002953073A0 (en) | 2002-11-21 | 2003-01-16 | Access Pharmaceuticals Australia Pty Limited | Amplification of biotin-mediated targeting |
| KR100578382B1 (ko) | 2004-07-16 | 2006-05-11 | 나재운 | 항암제의 전달체용 수용성 키토산 나노입자 및 그 제조방법 |
| US7846893B2 (en) | 2005-02-16 | 2010-12-07 | Rutgers, The State University Of New Jersey | Drug-polymer conjugates coupled to a peptidic carrier |
| WO2007084126A1 (en) * | 2006-01-19 | 2007-07-26 | Allexcel, Inc. | Solubilization and targeted delivery of drugs with self-assembling amphiphilic polymers |
| BRPI0716808A2 (pt) | 2006-09-15 | 2013-11-05 | Enzon Pharmaceuticals Inc | Ligantes poliméricos baseados em lisina |
-
2009
- 2009-09-22 JP JP2011528068A patent/JP5539993B2/ja active Active
- 2009-09-22 US US13/120,140 patent/US9579400B2/en active Active
- 2009-09-22 WO PCT/US2009/057852 patent/WO2010039496A2/en not_active Ceased
- 2009-09-22 EP EP09740775.3A patent/EP2344134B1/en active Active
- 2009-09-22 CN CN2009801372511A patent/CN102159189B/zh active Active
-
2017
- 2017-01-23 US US15/412,912 patent/US10556021B2/en active Active
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