MX2011012823A - Conjugados peg-lípido puros. - Google Patents
Conjugados peg-lípido puros.Info
- Publication number
- MX2011012823A MX2011012823A MX2011012823A MX2011012823A MX2011012823A MX 2011012823 A MX2011012823 A MX 2011012823A MX 2011012823 A MX2011012823 A MX 2011012823A MX 2011012823 A MX2011012823 A MX 2011012823A MX 2011012823 A MX2011012823 A MX 2011012823A
- Authority
- MX
- Mexico
- Prior art keywords
- peg
- lipid
- glycerol
- composition
- group
- Prior art date
Links
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- 150000002632 lipids Chemical class 0.000 claims abstract description 70
- 239000000203 mixture Substances 0.000 claims description 91
- 239000000126 substance Substances 0.000 claims description 57
- 125000005647 linker group Chemical group 0.000 claims description 41
- 239000003613 bile acid Substances 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 239000013543 active substance Substances 0.000 claims description 22
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 16
- HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 claims description 15
- 125000003473 lipid group Chemical group 0.000 claims description 9
- 239000002502 liposome Substances 0.000 claims description 8
- 235000012000 cholesterol Nutrition 0.000 claims description 7
- 229930182912 cyclosporin Natural products 0.000 claims description 6
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 claims description 5
- 229960001265 ciclosporin Drugs 0.000 claims description 5
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- 229930105110 Cyclosporin A Natural products 0.000 claims description 3
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 46
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 21
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
- 150000003573 thiols Chemical class 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
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- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 11
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
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- IIRDTKBZINWQAW-UHFFFAOYSA-N hexaethylene glycol Chemical compound OCCOCCOCCOCCOCCOCCO IIRDTKBZINWQAW-UHFFFAOYSA-N 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 10
- 125000002730 succinyl group Chemical group C(CCC(=O)*)(=O)* 0.000 description 10
- VHVPQPYKVGDNFY-DFMJLFEVSA-N 2-[(2r)-butan-2-yl]-4-[4-[4-[4-[[(2r,4s)-2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-1,2,4-triazol-3-one Chemical compound O=C1N([C@H](C)CC)N=CN1C1=CC=C(N2CCN(CC2)C=2C=CC(OC[C@@H]3O[C@](CN4N=CN=C4)(OC3)C=3C(=CC(Cl)=CC=3)Cl)=CC=2)C=C1 VHVPQPYKVGDNFY-DFMJLFEVSA-N 0.000 description 9
- 239000012043 crude product Substances 0.000 description 9
- 229960004130 itraconazole Drugs 0.000 description 9
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 9
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 9
- 239000002775 capsule Substances 0.000 description 8
- 150000004665 fatty acids Chemical class 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical class OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 8
- OWVYGSGZMWWQQY-UHFFFAOYSA-N 2-[2-[2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]-1-methoxyethanol Chemical compound COC(O)COCCOCCOCCOCCOCCO OWVYGSGZMWWQQY-UHFFFAOYSA-N 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
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- 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
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Applications Claiming Priority (3)
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| US21762709P | 2009-06-02 | 2009-06-02 | |
| US28406509P | 2009-12-12 | 2009-12-12 | |
| PCT/US2010/001590 WO2010141069A2 (en) | 2009-06-02 | 2010-06-01 | Pure peg-lipid conjugates |
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| Publication Number | Publication Date |
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| MX2011012823A true MX2011012823A (es) | 2012-06-25 |
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| MX2011012823A MX2011012823A (es) | 2009-06-02 | 2010-06-01 | Conjugados peg-lípido puros. |
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| CN (1) | CN102665685A (enExample) |
| AP (1) | AP2012006053A0 (enExample) |
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Families Citing this family (50)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9393315B2 (en) | 2011-06-08 | 2016-07-19 | Nitto Denko Corporation | Compounds for targeting drug delivery and enhancing siRNA activity |
| US20120202890A1 (en) | 2011-02-08 | 2012-08-09 | Nian Wu | Polymer-carbohydrate-lipid conjugates |
| US20120232169A1 (en) * | 2011-03-07 | 2012-09-13 | Biozone Pharmaceuticals, Inc. | Highly monodisperse branched peg-lipid conjugates |
| US10196637B2 (en) | 2011-06-08 | 2019-02-05 | Nitto Denko Corporation | Retinoid-lipid drug carrier |
| US8883177B2 (en) * | 2011-06-28 | 2014-11-11 | Nian Wu | Pharmaceutical compositions for parenteral administration |
| JP6051758B2 (ja) * | 2011-10-17 | 2016-12-27 | 日油株式会社 | ジアシルグリセロールと結合した分岐型ポリエチレングリコール、その製造方法およびポリエチレングリコール修飾リポソーム |
| MX363822B (es) * | 2012-08-21 | 2019-04-04 | Opko Pharmaceuticals Llc | Formulaciones de liposomas. |
| US11458199B2 (en) | 2012-08-21 | 2022-10-04 | Opko Pharmaceuticals, Llc | Liposome formulations |
| US8980839B2 (en) | 2012-08-24 | 2015-03-17 | Ocular Technologies Sarl | Topical aqueous nanomicellar, ophthalmic solutions and uses thereof |
| WO2015021044A1 (en) * | 2013-08-05 | 2015-02-12 | University Of Rochester | Compositions and methods for stimuli-responsive release of a therapeutic agent |
| CN105792850A (zh) * | 2013-12-05 | 2016-07-20 | 念·吴 | 聚合物-碳水化合物的缀合物的药物转递技术 |
| JP6629736B2 (ja) * | 2013-12-20 | 2020-01-15 | エフ.ホフマン−ラ ロシュ アーゲーF. Hoffmann−La Roche Aktiengesellschaft | 1以上の疎水性ドメインおよびpeg部分を含む親水性ドメインを含む、細胞を結合するのに有用な化合物 |
| CN105829886B (zh) | 2013-12-20 | 2018-04-03 | 豪夫迈·罗氏有限公司 | 使用包含聚乙二醇部分的化合物在支持物上固定细胞的方法 |
| JP6461973B2 (ja) * | 2013-12-20 | 2019-01-30 | エフ.ホフマン−ラ ロシュ アーゲーF. Hoffmann−La Roche Aktiengesellschaft | 2以上の疎水性ドメインおよびpeg部分を含む親水性ドメインを含む化合物の、細胞の安定化のための使用 |
| AU2015360794B2 (en) | 2014-12-08 | 2021-07-08 | The Board Of Regents Of The University Of Texas System | Lipocationic polymers and uses thereof |
| US10064954B2 (en) | 2015-06-23 | 2018-09-04 | Nian Wu | Polymer-cyclodextrin-lipid conjugates |
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| EP3770143A4 (en) * | 2018-03-20 | 2021-12-22 | NOF Corporation | BRANCHIFIED SINGLE-DISPERSED POLYETHYLENE GLYCOL, INTERMEDIATE AND ASSOCIATED PRODUCTION PROCESS |
| CA3095299A1 (en) * | 2018-03-29 | 2019-10-03 | Nof Corporation | Method for purifying trityl group-containing monodispersed polyethylene glycol |
| WO2019191597A1 (en) * | 2018-03-30 | 2019-10-03 | The Board Of Regents Of The University Of Oklahoma | Very long chain saturated fatty acid compounds, compositions containing same, and methods of use |
| US12357580B2 (en) | 2018-06-19 | 2025-07-15 | The Board Of Regents Of The University Of Texas System | Lipid nanoparticle compositions for delivery of mRNA and long nucleic acids |
| CN112996519B (zh) | 2018-09-04 | 2025-02-28 | 德克萨斯大学系统董事会 | 用于核酸的器官特异性递送的组合物和方法 |
| AU2019335055B2 (en) | 2018-09-04 | 2025-05-29 | The Board Of Regents Of The University Of Texas System | Compositions and methods for organ specific delivery of nucleic acids |
| US12383508B2 (en) * | 2018-09-19 | 2025-08-12 | Modernatx, Inc. | High-purity peg lipids and uses thereof |
| JP6805385B1 (ja) * | 2020-08-31 | 2020-12-23 | ジェイ−ネットワーク,インコーポレイテッド | 表皮内の保湿関連物質の発現増強剤 |
| CN116615235A (zh) | 2020-10-09 | 2023-08-18 | 得克萨斯州大学系统董事会 | 融合前稳定的hmpv f蛋白 |
| JP6860739B1 (ja) * | 2020-11-20 | 2021-04-21 | ジェイ−ネットワーク,インコーポレイテッド | 表皮内の抗酸化物質の発現増強剤 |
| CN114685778B (zh) * | 2020-12-30 | 2023-10-17 | 苏州艾博生物科技有限公司 | 长循环阳离子脂质体的合成方法 |
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| IL306007A (en) | 2021-03-23 | 2023-11-01 | Recode Therapeutics Inc | Polynucleotide preparations, related formulations and methods of using them |
| US20240207442A1 (en) | 2021-04-22 | 2024-06-27 | The Board Of Regents Of The University Of Texas System | All-in-one dendrimer-based lipid nanoparticles enable precise hdr-mediated gene editing in vivo |
| EP4342929A4 (en) | 2021-06-30 | 2024-10-30 | Jenkem Technology Co. Ltd. (Tianjin) | POLYETHYLENE GLYCOL LIPID AND ITS USE |
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| CN116410460B (zh) * | 2021-12-29 | 2025-08-05 | 辅必成(上海)医药科技有限公司 | 一种1,2-二肉豆蔻酰-rac-甘油-3-甲氧基聚乙二醇2000的制备方法 |
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| US20250235404A1 (en) * | 2022-04-05 | 2025-07-24 | Capstan Therapeutics, Inc. | Peg-lipids and lipid nanoparticles |
| CN114524943B (zh) * | 2022-04-22 | 2022-09-16 | 天津凯莱英制药有限公司 | 聚乙二醇-甘油衍生物及其中间体各自的制备方法 |
| CN117003807A (zh) * | 2022-04-28 | 2023-11-07 | 北京科兴中维生物技术有限公司 | 一种结构脂质化合物及其制备方法和用途 |
| IL320164A (en) * | 2022-11-15 | 2025-06-01 | Evonik Operations Gmbh | Polyoxyalkylene-2,1-dimyristoyl-glycerol compounds where the polyoxyalkylene is poly(ethylene oxide) having C1 to C3-alkyloxymethyl side chains |
| WO2024123633A1 (en) | 2022-12-08 | 2024-06-13 | Recode Therapeutics, Inc. | Lipid nanoparticle compositions and uses thereof |
| CN120569211A (zh) | 2023-01-09 | 2025-08-29 | 得克萨斯州大学系统董事会 | 融合前稳定的人副流感病毒3f蛋白 |
| CN116178733B (zh) * | 2023-03-03 | 2023-08-01 | 浙江博美生物技术有限公司 | 一种基于三官能团氨基酸的支化单分散peg衍生物、制备方法和应用 |
| US12364773B2 (en) | 2023-12-01 | 2025-07-22 | Recode Therapeutics, Inc. | Lipid nanoparticle compositions and uses thereof |
| WO2025137646A1 (en) | 2023-12-22 | 2025-06-26 | Recode Therapeutics, Inc. | Gene editing methods and compositions for treating cystic fibrosis |
Family Cites Families (6)
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|---|---|---|---|---|
| US5827533A (en) * | 1997-02-06 | 1998-10-27 | Duke University | Liposomes containing active agents aggregated with lipid surfactants |
| US7141552B2 (en) * | 2000-01-10 | 2006-11-28 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Use of lipid conjugates in the treatment of diseases |
| NZ581166A (en) * | 2003-09-15 | 2011-06-30 | Protiva Biotherapeutics Inc | Polyethyleneglycol-modified lipid compounds and uses thereof |
| WO2006007712A1 (en) * | 2004-07-19 | 2006-01-26 | Protiva Biotherapeutics, Inc. | Methods comprising polyethylene glycol-lipid conjugates for delivery of therapeutic agents |
| WO2006051405A2 (en) * | 2004-11-12 | 2006-05-18 | Cambridge University Technical Services Ltd. | Methods and means related to cancer stem cells |
| EP2219587A4 (en) * | 2007-11-14 | 2012-11-21 | Univ California | STEROL-MODIFIED AMPHIPHILE LIPIDES |
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| BRPI1010175A2 (pt) | 2016-03-29 |
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| IL216719A0 (en) | 2012-02-29 |
| JP2012528857A (ja) | 2012-11-15 |
| CL2011003049A1 (es) | 2012-07-13 |
| ZA201109366B (en) | 2012-08-29 |
| AU2010257181A1 (en) | 2012-01-12 |
| CN102665685A (zh) | 2012-09-12 |
| CA2763819A1 (en) | 2010-12-09 |
| KR20120039564A (ko) | 2012-04-25 |
| WO2010141069A2 (en) | 2010-12-09 |
| US20110040113A1 (en) | 2011-02-17 |
| AP2012006053A0 (en) | 2012-02-29 |
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