JP2012509272A5 - - Google Patents
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- JP2012509272A5 JP2012509272A5 JP2011536583A JP2011536583A JP2012509272A5 JP 2012509272 A5 JP2012509272 A5 JP 2012509272A5 JP 2011536583 A JP2011536583 A JP 2011536583A JP 2011536583 A JP2011536583 A JP 2011536583A JP 2012509272 A5 JP2012509272 A5 JP 2012509272A5
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- JP
- Japan
- Prior art keywords
- substituted
- alkyl
- nhc
- compound
- group
- 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.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 claims 28
- 239000002105 nanoparticle Substances 0.000 claims 28
- 150000001875 compounds Chemical class 0.000 claims 25
- 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 22
- 239000000203 mixture Substances 0.000 claims 22
- 229910052739 hydrogen Inorganic materials 0.000 claims 19
- 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims 15
- 108091034117 Oligonucleotide Proteins 0.000 claims 15
- 239000001257 hydrogen Substances 0.000 claims 13
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 13
- 235000012000 cholesterol Nutrition 0.000 claims 11
- 125000000547 substituted alkyl group Chemical group 0.000 claims 11
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 11
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 10
- 125000003118 aryl group Chemical group 0.000 claims 10
- 150000002632 lipids Chemical class 0.000 claims 10
- 230000000692 anti-sense effect Effects 0.000 claims 9
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 229910052799 carbon Inorganic materials 0.000 claims 8
- 125000004405 heteroalkoxy group Chemical group 0.000 claims 8
- 125000001072 heteroaryl group Chemical group 0.000 claims 8
- 108020004707 nucleic acids Proteins 0.000 claims 8
- 102000039446 nucleic acids Human genes 0.000 claims 8
- 150000007523 nucleic acids Chemical class 0.000 claims 8
- 125000003107 substituted aryl group Chemical group 0.000 claims 8
- 125000004423 acyloxy group Chemical group 0.000 claims 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 6
- 150000001412 amines Chemical class 0.000 claims 5
- 229940106189 ceramide Drugs 0.000 claims 5
- 125000004404 heteroalkyl group Chemical group 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 claims 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims 4
- 125000005199 aryl carbonyloxy group Chemical group 0.000 claims 4
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 150000008104 phosphatidylethanolamines Chemical class 0.000 claims 4
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 3
- 229920000362 Polyethylene-block-poly(ethylene glycol) Polymers 0.000 claims 3
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 3
- -1 aryl mercapto Chemical class 0.000 claims 3
- 230000001588 bifunctional effect Effects 0.000 claims 3
- 125000001589 carboacyl group Chemical group 0.000 claims 3
- 230000000799 fusogenic effect Effects 0.000 claims 3
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 3
- 108091023037 Aptamer Proteins 0.000 claims 2
- YDNKGFDKKRUKPY-JHOUSYSJSA-N C16 ceramide Natural products CCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)C=CCCCCCCCCCCCCC YDNKGFDKKRUKPY-JHOUSYSJSA-N 0.000 claims 2
- 108700011259 MicroRNAs Proteins 0.000 claims 2
- CRJGESKKUOMBCT-VQTJNVASSA-N N-acetylsphinganine Chemical compound CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO)NC(C)=O CRJGESKKUOMBCT-VQTJNVASSA-N 0.000 claims 2
- 108091093037 Peptide nucleic acid Proteins 0.000 claims 2
- 108020004459 Small interfering RNA Proteins 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000004104 aryloxy group Chemical group 0.000 claims 2
- ZVEQCJWYRWKARO-UHFFFAOYSA-N ceramide Natural products CCCCCCCCCCCCCCC(O)C(=O)NC(CO)C(O)C=CCCC=C(C)CCCCCCCCC ZVEQCJWYRWKARO-UHFFFAOYSA-N 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000002679 microRNA Substances 0.000 claims 2
- VVGIYYKRAMHVLU-UHFFFAOYSA-N newbouldiamide Natural products CCCCCCCCCCCCCCCCCCCC(O)C(O)C(O)C(CO)NC(=O)CCCCCCCCCCCCCCCCC VVGIYYKRAMHVLU-UHFFFAOYSA-N 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 239000002773 nucleotide Substances 0.000 claims 2
- 125000003729 nucleotide group Chemical group 0.000 claims 2
- 229910052698 phosphorus Inorganic materials 0.000 claims 2
- 239000004055 small Interfering RNA Substances 0.000 claims 2
- 125000006850 spacer group Chemical group 0.000 claims 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- NRJAVPSFFCBXDT-HUESYALOSA-N 1,2-distearoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCC NRJAVPSFFCBXDT-HUESYALOSA-N 0.000 claims 1
- FWMNVWWHGCHHJJ-SKKKGAJSSA-N 4-amino-1-[(2r)-6-amino-2-[[(2r)-2-[[(2r)-2-[[(2r)-2-amino-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoyl]amino]hexanoyl]piperidine-4-carboxylic acid Chemical compound C([C@H](C(=O)N[C@H](CC(C)C)C(=O)N[C@H](CCCCN)C(=O)N1CCC(N)(CC1)C(O)=O)NC(=O)[C@H](N)CC=1C=CC=CC=1)C1=CC=CC=C1 FWMNVWWHGCHHJJ-SKKKGAJSSA-N 0.000 claims 1
- 102100021569 Apoptosis regulator Bcl-2 Human genes 0.000 claims 1
- 102100021663 Baculoviral IAP repeat-containing protein 5 Human genes 0.000 claims 1
- 108060000903 Beta-catenin Proteins 0.000 claims 1
- 102000015735 Beta-catenin Human genes 0.000 claims 1
- 102000053642 Catalytic RNA Human genes 0.000 claims 1
- 108090000994 Catalytic RNA Proteins 0.000 claims 1
- 108010045100 HSP27 Heat-Shock Proteins Proteins 0.000 claims 1
- 102100039165 Heat shock protein beta-1 Human genes 0.000 claims 1
- 101000971171 Homo sapiens Apoptosis regulator Bcl-2 Proteins 0.000 claims 1
- 101001046870 Homo sapiens Hypoxia-inducible factor 1-alpha Proteins 0.000 claims 1
- 101000605639 Homo sapiens Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform Proteins 0.000 claims 1
- 102100022875 Hypoxia-inducible factor 1-alpha Human genes 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 102100038332 Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform Human genes 0.000 claims 1
- 108091030071 RNAI Proteins 0.000 claims 1
- 108091028664 Ribonucleotide Proteins 0.000 claims 1
- 108091027076 Spiegelmer Proteins 0.000 claims 1
- 108010002687 Survivin Proteins 0.000 claims 1
- 108010088665 Zinc Finger Protein Gli2 Proteins 0.000 claims 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 102000001307 androgen receptors Human genes 0.000 claims 1
- 108010080146 androgen receptors Proteins 0.000 claims 1
- 150000001540 azides Chemical class 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 125000003178 carboxy group Chemical class [H]OC(*)=O 0.000 claims 1
- 125000004093 cyano group Chemical class *C#N 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 230000009368 gene silencing by RNA Effects 0.000 claims 1
- 125000001475 halogen functional group Chemical class 0.000 claims 1
- 150000002466 imines Chemical class 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- KITHNHJPIHPBQH-UHFFFAOYSA-N nitro(nitrosilyloxy)silane Chemical class [N+](=O)([O-])[SiH2]O[SiH2][N+](=O)[O-] KITHNHJPIHPBQH-UHFFFAOYSA-N 0.000 claims 1
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 claims 1
- 230000035755 proliferation Effects 0.000 claims 1
- 239000002336 ribonucleotide Substances 0.000 claims 1
- 125000002652 ribonucleotide group Chemical group 0.000 claims 1
- 108091092562 ribozyme Proteins 0.000 claims 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 1
- 125000000472 sulfonyl group Chemical class *S(*)(=O)=O 0.000 claims 1
- 0 CC(C)CCCCC(CC1)C(C)(CC2)C1C1C2C(C)(CCC(C2)OC(C(C*)*=C)=O)C2=CC1 Chemical compound CC(C)CCCCC(CC1)C(C)(CC2)C1C1C2C(C)(CCC(C2)OC(C(C*)*=C)=O)C2=CC1 0.000 description 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11534808P | 2008-11-17 | 2008-11-17 | |
| US11536508P | 2008-11-17 | 2008-11-17 | |
| US11528708P | 2008-11-17 | 2008-11-17 | |
| US61/115,348 | 2008-11-17 | ||
| US61/115,287 | 2008-11-17 | ||
| US61/115,365 | 2008-11-17 | ||
| PCT/US2009/064719 WO2010057155A1 (en) | 2008-11-17 | 2009-11-17 | Releasable cationic lipids for nucleic acids delivery systems |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2012509272A JP2012509272A (ja) | 2012-04-19 |
| JP2012509272A5 true JP2012509272A5 (enExample) | 2012-12-27 |
Family
ID=42170406
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011536583A Pending JP2012509272A (ja) | 2008-11-17 | 2009-11-17 | 核酸送達系のための放出性カチオン脂質 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20110229581A1 (enExample) |
| EP (1) | EP2364085A4 (enExample) |
| JP (1) | JP2012509272A (enExample) |
| CN (1) | CN102231952A (enExample) |
| CA (1) | CA2742776A1 (enExample) |
| TW (1) | TW201021853A (enExample) |
| WO (1) | WO2010057155A1 (enExample) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2742689A1 (en) * | 2008-11-17 | 2010-05-20 | Enzon Pharmaceuticals, Inc. | Branched cationic lipids for nucleic acids delivery system |
| CN101870719B (zh) * | 2010-05-21 | 2013-09-25 | 中国科学院上海有机化学研究所 | 一种同时具有二硫化学键和甾体骨架结构的有机功能化合物、制备方法和用途 |
| CN102161688B (zh) * | 2011-02-18 | 2013-09-04 | 中国科学院上海有机化学研究所 | 一种含有胆固醇结构片段的生物相容性合成脂质体、制备方法及其应用 |
| CN104011210B (zh) | 2011-10-11 | 2018-05-01 | 布里格姆及妇女医院股份有限公司 | 神经退行性病症中的microRNA |
| US9579338B2 (en) | 2011-11-04 | 2017-02-28 | Nitto Denko Corporation | Method of producing lipid nanoparticles for drug delivery |
| CN103906504B (zh) * | 2011-11-04 | 2017-11-17 | 日东电工株式会社 | 制备用于药物递送的脂质纳米颗粒的方法 |
| CA2858884A1 (en) | 2011-12-12 | 2013-06-20 | The Trustees Of The University Of Pennsylvania | Proteins comprising mrsa pbp2a and fragments thereof, nucleic acids encoding the same, and compositions and their use to prevent and treat mrsa infections |
| CN102911252B (zh) * | 2012-10-25 | 2014-07-16 | 四川大学 | 含肽类树状分子的阳离子脂质、转基因载体及其制备方法和应用 |
| AU2013355258A1 (en) * | 2012-12-07 | 2015-06-11 | Alnylam Pharmaceuticals, Inc. | Improved nucleic acid lipid particle formulations |
| DK2992874T3 (en) | 2013-04-30 | 2018-11-12 | Delta Fly Pharma Inc | LIPOSOM FOR TOPIC SUBMISSION AND USE THEREOF |
| JP5914418B2 (ja) * | 2013-06-26 | 2016-05-11 | 富士フイルム株式会社 | 脂質粒子、核酸送達キャリア、核酸送達キャリア製造用組成物、脂質粒子の製造方法及び遺伝子導入方法 |
| WO2015021465A2 (en) * | 2013-08-09 | 2015-02-12 | New York University | Protein engineered systems for delivery of molecules |
| WO2015178438A1 (ja) * | 2014-05-20 | 2015-11-26 | アルケア株式会社 | 皮膚用粘着剤組成物及び皮膚用貼付材 |
| AU2015337909B2 (en) | 2014-10-30 | 2018-12-13 | Delta-Fly Pharma, Inc. | New production method of lipoplex for local administration and antitumor drug using lipoplex |
| CN107406396B (zh) * | 2015-01-30 | 2021-02-26 | 日油株式会社 | 阳离子性脂质 |
| US11459568B2 (en) | 2016-10-31 | 2022-10-04 | University Of Massachusetts | Targeting microRNA-101-3p in cancer therapy |
| EP3315125A1 (en) * | 2016-10-31 | 2018-05-02 | Silence Therapeutics (London) Ltd | Lipid nanoparticle formulation |
| CN106565763B (zh) * | 2016-11-11 | 2017-12-15 | 深圳市声光动力生物医药科技有限公司 | pH敏感的轴向取代硅酞菁配合物及其制备方法和在医药上的应用 |
| CN113166783B (zh) | 2018-10-09 | 2024-10-11 | 不列颠哥伦比亚大学 | 包含无有机溶剂和去污剂的转染活性囊泡的组合物和系统以及与之相关的方法 |
| AU2020204989A1 (en) * | 2019-01-04 | 2021-07-08 | Elevatebio Technologies, Inc. | Encapsulated RNA polynucleotides and methods of use |
| CN111072504A (zh) * | 2019-12-31 | 2020-04-28 | 芜湖天道绿色新材料有限公司 | 一种可降解固化剂的一步制备方法 |
| CN114522252B (zh) * | 2022-04-24 | 2023-08-04 | 天津外泌体科技有限公司 | 一步法叠氮化修饰细胞外囊泡的方法及修饰试剂 |
| CN114984236B (zh) * | 2022-04-29 | 2023-03-24 | 深圳近邻生物科技有限公司 | 一种响应型核酸递送系统及其制备方法、交联聚合物载体 |
| CN120659770A (zh) * | 2023-03-22 | 2025-09-16 | 上海环码生物医药有限公司 | 脂质化合物、脂质纳米颗粒和药物组合物 |
| WO2024201465A1 (en) * | 2023-03-27 | 2024-10-03 | Aposense Ltd. | Peptide trans-membrane delivery systems and uses thereof |
| CN120227354A (zh) * | 2023-12-29 | 2025-07-01 | 康希诺(上海)生物研发有限公司 | 一种用于递送核酸的脂质纳米颗粒及其制备方法和用途 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6383814B1 (en) * | 1994-12-09 | 2002-05-07 | Genzyme Corporation | Cationic amphiphiles for intracellular delivery of therapeutic molecules |
| US6071890A (en) * | 1994-12-09 | 2000-06-06 | Genzyme Corporation | Organ-specific targeting of cationic amphiphile/DNA complexes for gene therapy |
| CA2289702C (en) * | 1997-05-14 | 2008-02-19 | Inex Pharmaceuticals Corp. | High efficiency encapsulation of charged therapeutic agents in lipid vesicles |
| US6794499B2 (en) * | 1997-09-12 | 2004-09-21 | Exiqon A/S | Oligonucleotide analogues |
| US6841537B1 (en) * | 1998-04-22 | 2005-01-11 | Protiva Biotherapeutics Inc. | Combination therapy using nucleic acids and conventional drugs |
| US6169078B1 (en) * | 1998-05-12 | 2001-01-02 | University Of Florida | Materials and methods for the intracellular delivery of substances |
| FR2813794B1 (fr) * | 2000-09-08 | 2003-01-24 | Pasteur Institut | Procede de couplage, en solution, entre un peptide et un vecteur lipophile et ses applications |
| US20030077829A1 (en) * | 2001-04-30 | 2003-04-24 | Protiva Biotherapeutics Inc.. | Lipid-based formulations |
| US20070042983A1 (en) * | 2001-05-18 | 2007-02-22 | Sirna Therapeutics, Inc. | RNA interference mediated inhibition of gene expression using short interfering nucleic acid (siNA) |
| US20050222064A1 (en) * | 2002-02-20 | 2005-10-06 | Sirna Therapeutics, Inc. | Polycationic compositions for cellular delivery of polynucleotides |
| AU2004272646B2 (en) * | 2003-09-15 | 2011-11-24 | Arbutus Biopharma Corporation | 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 |
| CA2597724A1 (en) * | 2005-02-14 | 2007-08-02 | Sirna Therapeutics, Inc. | Cationic lipids and formulated molecular compositions containing them |
| US7404969B2 (en) * | 2005-02-14 | 2008-07-29 | Sirna Therapeutics, Inc. | Lipid nanoparticle based compositions and methods for the delivery of biologically active molecules |
| WO2007090194A2 (en) * | 2006-02-01 | 2007-08-09 | The Burnham Institute For Medical Research | Lymphatic zip codes in tumors and pre-malignant lesions |
| US20070293449A1 (en) * | 2006-06-20 | 2007-12-20 | Nastech Pharmaceutical Company Inc. | Compositions and methods for delivery of double-stranded rna |
| WO2008043366A2 (en) * | 2006-10-13 | 2008-04-17 | Københavns Universitet | Three-domain compounds for transmembrane delivery |
| CA2742689A1 (en) * | 2008-11-17 | 2010-05-20 | Enzon Pharmaceuticals, Inc. | Branched cationic lipids for nucleic acids delivery system |
| EP2355799A4 (en) * | 2008-11-17 | 2012-09-05 | Enzon Pharmaceuticals Inc | CLEANABLE FUSOGENIC LIPIDS FOR NUCLEIC ACID RELIEF SYSTEMS |
-
2009
- 2009-11-17 JP JP2011536583A patent/JP2012509272A/ja active Pending
- 2009-11-17 CA CA2742776A patent/CA2742776A1/en not_active Abandoned
- 2009-11-17 CN CN2009801459229A patent/CN102231952A/zh active Pending
- 2009-11-17 WO PCT/US2009/064719 patent/WO2010057155A1/en not_active Ceased
- 2009-11-17 TW TW098138946A patent/TW201021853A/zh unknown
- 2009-11-17 US US13/129,611 patent/US20110229581A1/en not_active Abandoned
- 2009-11-17 EP EP09826950A patent/EP2364085A4/en not_active Withdrawn
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