CA2671873C - Oligonucleotides containing high concentrations of guanine monomers - Google Patents
Oligonucleotides containing high concentrations of guanine monomers Download PDFInfo
- Publication number
- CA2671873C CA2671873C CA2671873A CA2671873A CA2671873C CA 2671873 C CA2671873 C CA 2671873C CA 2671873 A CA2671873 A CA 2671873A CA 2671873 A CA2671873 A CA 2671873A CA 2671873 C CA2671873 C CA 2671873C
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- CA
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- Prior art keywords
- oligonucleotide
- solvent
- coupling
- seq
- nucleoside
- 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.)
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- 108091034117 Oligonucleotide Proteins 0.000 title claims abstract description 146
- 239000000178 monomer Substances 0.000 title claims abstract description 75
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 title claims abstract description 66
- JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 title abstract description 18
- 238000005859 coupling reaction Methods 0.000 claims abstract description 107
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- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 48
- 239000003153 chemical reaction reagent Substances 0.000 claims description 29
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 29
- 230000003213 activating effect Effects 0.000 claims description 25
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 claims description 24
- 239000004793 Polystyrene Substances 0.000 claims description 23
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 22
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- 239000002773 nucleotide Substances 0.000 claims description 11
- 125000003729 nucleotide group Chemical group 0.000 claims description 11
- 238000005571 anion exchange chromatography Methods 0.000 claims description 10
- 108091081548 Palindromic sequence Proteins 0.000 claims description 9
- NYHBQMYGNKIUIF-UUOKFMHZSA-N Guanosine Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O NYHBQMYGNKIUIF-UUOKFMHZSA-N 0.000 claims description 8
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- 238000010511 deprotection reaction Methods 0.000 claims description 5
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 4
- GONFBOIJNUKKST-UHFFFAOYSA-N 5-ethylsulfanyl-2h-tetrazole Chemical compound CCSC=1N=NNN=1 GONFBOIJNUKKST-UHFFFAOYSA-N 0.000 claims description 4
- MIKUYHXYGGJMLM-GIMIYPNGSA-N Crotonoside Natural products C1=NC2=C(N)NC(=O)N=C2N1[C@H]1O[C@@H](CO)[C@H](O)[C@@H]1O MIKUYHXYGGJMLM-GIMIYPNGSA-N 0.000 claims description 4
- NYHBQMYGNKIUIF-UHFFFAOYSA-N D-guanosine Natural products C1=2NC(N)=NC(=O)C=2N=CN1C1OC(CO)C(O)C1O NYHBQMYGNKIUIF-UHFFFAOYSA-N 0.000 claims description 4
- 229940029575 guanosine Drugs 0.000 claims description 4
- GXGKKIPUFAHZIZ-UHFFFAOYSA-N 5-benzylsulfanyl-2h-tetrazole Chemical compound C=1C=CC=CC=1CSC=1N=NNN=1 GXGKKIPUFAHZIZ-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Substances C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 claims 1
- 238000002515 oligonucleotide synthesis Methods 0.000 abstract description 5
- 239000000243 solution Substances 0.000 description 63
- 239000000047 product Substances 0.000 description 41
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 32
- 108020004414 DNA Proteins 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
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- SSJJWVREPZVNBF-DGXVIIAXSA-N dG10 Chemical compound C1=NC(C(NC(N)=N2)=O)=C2N1[C@H](O[C@@H]1COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C3=C(C(NC(N)=N3)=O)N=C2)CO)C[C@@H]1OP(O)(=O)OC[C@@H](O1)[C@@H](O)C[C@@H]1N1C(N=C(NC2=O)N)=C2N=C1 SSJJWVREPZVNBF-DGXVIIAXSA-N 0.000 description 11
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- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- 230000006820 DNA synthesis Effects 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
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- GOMLCFUVZKLQCO-HTLAMOOLSA-N thrombin aptamer Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)O[C@H]2[C@H]([C@@H](O[C@@H]2COP(O)(=O)O[C@H]2[C@H]([C@@H](O[C@@H]2COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)O[C@H]2[C@H]([C@@H](O[C@@H]2COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)O[C@H]2[C@H]([C@@H](O[C@@H]2COP(O)(=O)O[C@H]2[C@H]([C@@H](O[C@@H]2COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)O[C@H]2[C@H]([C@@H](O[C@@H]2COP(O)(=O)O[C@H]2[C@H]([C@@H](O[C@@H]2CO)N2C3=C(C(NC(N)=N3)=O)N=C2)O)N2C3=C(C(NC(N)=N3)=O)N=C2)O)N2C3=C(C(NC(N)=N3)=O)N=C2)O)N2C3=C(C(NC(N)=N3)=O)N=C2)O)N2C3=C(C(NC(N)=N3)=O)N=C2)O)N2C3=C(C(NC(N)=N3)=O)N=C2)O)N2C3=C(C(NC(N)=N3)=O)N=C2)O)[C@@H](OP(O)(=O)OC[C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=C(C(NC(N)=N3)=O)N=C2)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=C(C(NC(N)=N3)=O)N=C2)O)C1 GOMLCFUVZKLQCO-HTLAMOOLSA-N 0.000 description 1
- 229940113082 thymine Drugs 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical class COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H21/00—Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H21/00—Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
- C07H21/02—Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids with ribosyl as saccharide radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Immunology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Saccharide Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US86958806P | 2006-12-12 | 2006-12-12 | |
| US60/869,588 | 2006-12-12 | ||
| PCT/US2007/087183 WO2008073960A2 (en) | 2006-12-12 | 2007-12-12 | Oligonucleotides containing high concentrations of guanine monomers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2671873A1 CA2671873A1 (en) | 2008-06-19 |
| CA2671873C true CA2671873C (en) | 2018-10-09 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2671873A Active CA2671873C (en) | 2006-12-12 | 2007-12-12 | Oligonucleotides containing high concentrations of guanine monomers |
Country Status (7)
| Country | Link |
|---|---|
| US (3) | US8586728B2 (enExample) |
| EP (1) | EP2125854B1 (enExample) |
| JP (1) | JP5389662B2 (enExample) |
| CN (1) | CN101611048B (enExample) |
| AU (1) | AU2007333147B2 (enExample) |
| CA (1) | CA2671873C (enExample) |
| WO (1) | WO2008073960A2 (enExample) |
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| DE102008063490B4 (de) * | 2008-12-17 | 2023-06-15 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtung und Verfahren zum Einstellen des Farbortes einer weiß emittierenden Elektrolumineszenzvorrichtung |
| WO2012059510A1 (en) | 2010-11-02 | 2012-05-10 | Girindus America, Inc. | Back pressure control during solid-phase synthesis on polymeric supports |
| US10040048B1 (en) | 2014-09-25 | 2018-08-07 | Synthego Corporation | Automated modular system and method for production of biopolymers |
| CN107428813B (zh) | 2014-12-31 | 2021-08-03 | 查克美特制药公司 | 组合肿瘤免疫疗法 |
| JP6891162B2 (ja) * | 2015-07-08 | 2021-06-18 | クロス バイオサイエンシズ アーゲー | グアニンリッチオリゴヌクレオチド |
| WO2017173334A1 (en) | 2016-04-01 | 2017-10-05 | Checkmate Pharmaceuticals, Inc. | Fc receptor-mediated drug delivery |
| US20190076814A1 (en) | 2017-09-11 | 2019-03-14 | Synthego Corporation | Biopolymer synthesis system and method |
| WO2019080704A1 (zh) * | 2017-10-25 | 2019-05-02 | 深圳华大生命科学研究院 | 用于核酸合成的微流控芯片 |
| WO2019160866A2 (en) | 2018-02-13 | 2019-08-22 | Checkmate Pharmaceuticals, Inc. | Compositions and methods for tumor immunotherapy |
| WO2019197965A1 (en) | 2018-04-09 | 2019-10-17 | Checkmate Pharmaceuticals | Packaging oligonucleotides into virus-like particles |
| AU2019340388B2 (en) * | 2018-09-11 | 2026-01-08 | Amgen Inc. | Purification methods for guanine-rich oligonucleotides |
| KR102899530B1 (ko) * | 2018-10-30 | 2025-12-15 | 도레이 카부시키가이샤 | 핵산의 비특이 결합 억제제, 하이브리디제이션용 시약, 및 핵산의 하이브리디제이션 방법 |
| CN112969527A (zh) * | 2018-11-08 | 2021-06-15 | 深圳华大生命科学研究院 | 一种微流控芯片及其制备方法和dna合成方法 |
| WO2021075423A1 (ja) * | 2019-10-18 | 2021-04-22 | 富士フイルム和光純薬株式会社 | ホスホロアミダイト活性化剤 |
| US20230322842A1 (en) * | 2020-04-14 | 2023-10-12 | Sumitomo Chemical Company, Limited | Composition containing nucleic acid oligomer |
| CN114425443B (zh) * | 2020-10-29 | 2025-10-31 | 江苏金斯瑞生物科技有限公司 | 一种寡核苷酸合成催化剂 |
| GB202114688D0 (en) | 2021-10-14 | 2021-12-01 | Exactmer Ltd | Solution phase polymer synthesis |
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| WO1984004749A1 (en) | 1983-06-01 | 1984-12-06 | Beckman Instruments Inc | Novel preparation of nucleoside phosphoramidite intermediates |
| US20030050263A1 (en) | 1994-07-15 | 2003-03-13 | The University Of Iowa Research Foundation | Methods and products for treating HIV infection |
| JP4111403B2 (ja) | 1996-10-11 | 2008-07-02 | ザ リージェンツ オブ ザ ユニバーシティー オブ カリフォルニア | 免疫刺激ポリヌクレオチド／免疫調節分子複合体 |
| AU7350798A (en) | 1997-04-29 | 1998-11-24 | Universiteit Utrecht | Corona virus-like particles as tools for vaccination and therapy |
| CA2288129A1 (en) | 1997-05-01 | 1998-11-12 | Chiron Corporation | Use of virus-like particles as adjuvants |
| US6171591B1 (en) | 1997-12-08 | 2001-01-09 | Pentamer Pharmaceuticals, Inc. | Recombinant nodavirus compositions and methods |
| US6541438B1 (en) | 1998-05-01 | 2003-04-01 | The Procter & Gamble Company | Laundry detergent and/or fabric care compositions comprising a modified cellulase |
| ATE314095T1 (de) | 1998-10-21 | 2006-01-15 | Us Health | Virusähnliche partikel zur induktion von autoantikörpern |
| AU768807B2 (en) | 1998-11-30 | 2004-01-08 | Cytos Biotechnology Ag | Ordered molecular presentation of antigens, method of preparation and use |
| EP1165773A4 (en) | 1999-02-02 | 2005-01-05 | Biocache Pharmaceuticals Inc | IMPROVED PLATFORM FOR PRESENTING ANTIGENS |
| EP2286792A1 (en) | 1999-02-26 | 2011-02-23 | Novartis Vaccines and Diagnostics, Inc. | Microemulsions with an adsorbent surface, comprising a microdroplet emulsion |
| KR100863630B1 (ko) | 1999-09-25 | 2008-10-15 | 유니버시티 오브 아이오와 리써치 파운데이션 | 면역자극성 핵산 |
| US6949520B1 (en) | 1999-09-27 | 2005-09-27 | Coley Pharmaceutical Group, Inc. | Methods related to immunostimulatory nucleic acid-induced interferon |
| IL148844A0 (en) | 1999-09-27 | 2002-09-12 | Coley Pharm Group Inc | Methods related to immunostimulatory nucleic acid-induced interferon |
| ATE454901T1 (de) | 1999-10-13 | 2010-01-15 | Novartis Vaccines & Diagnostic | Verfahren zur erhaltung zellimmuneantworten gegen proteinen |
| DE60018601T4 (de) | 1999-11-24 | 2008-05-21 | Chiron Corp., Emeryville | HBV/HCV Virus-ähnliche Partikel |
| AT409085B (de) | 2000-01-28 | 2002-05-27 | Cistem Biotechnologies Gmbh | Pharmazeutische zusammensetzung zur immunmodulation und herstellung von vakzinen |
| EP1261366A4 (en) | 2000-02-24 | 2003-06-18 | Univ Leland Stanford Junior | ADJUVANT TREATMENT BY IN VIVO ACTIVATION OF DENDRITIC CELLS |
| AU2002248185A1 (en) | 2000-12-14 | 2002-07-16 | Coley Pharmaceutical Group, Inc. | Inhibition of angiogenesis by nucleic acids |
| US20030050268A1 (en) | 2001-03-29 | 2003-03-13 | Krieg Arthur M. | Immunostimulatory nucleic acid for treatment of non-allergic inflammatory diseases |
| AU2002347404A1 (en) | 2001-09-14 | 2003-04-01 | Cytos Biotechnology Ag | In vivo activation of antigen presenting cells for enhancement of immune responses induced by virus like particles |
| DE60234375D1 (de) | 2001-09-14 | 2009-12-24 | Cytos Biotechnology Ag | VERPACKUNG VON IMMUNSTIMULIERENDEM CpG IN VIRUSÄHNLICHEN PARTIKELN: HERSTELLUNGSVERFAHREN UND VERWENDUNG |
| US7524950B2 (en) * | 2001-10-31 | 2009-04-28 | Agilent Technologies, Inc. | Uses of cationic salts for polynucleotide synthesis |
| CA2488856A1 (en) | 2002-06-20 | 2003-12-31 | Cytos Biotechnology Ag | Packaged virus-like particles for use as adjuvants: method of preparation and use |
| US7537767B2 (en) | 2003-03-26 | 2009-05-26 | Cytis Biotechnology Ag | Melan-A- carrier conjugates |
| US20060210588A1 (en) | 2003-03-26 | 2006-09-21 | Cytos Biotechnology Ag | Hiv-peptide-carrier-conjugates |
| EP1605973B1 (en) | 2003-03-26 | 2012-09-26 | Cytos Biotechnology AG | Packaging of immunostimulatory oligonucleotides into virus-like particles: methods of preparation and uses |
| US20060251623A1 (en) | 2003-07-10 | 2006-11-09 | Caytos Biotechnology Ag | Packaged virus-like particles |
| CA2544240A1 (en) * | 2003-07-22 | 2005-02-17 | Cytos Biotechnology Ag | Cpg-packaged liposomes |
| JP4628686B2 (ja) | 2004-02-25 | 2011-02-09 | 独立行政法人科学技術振興機構 | ホスホロアミダイトを含む３’末端ヌクレオシドユニット |
| EP1789460B1 (en) * | 2004-09-02 | 2013-01-09 | Isis Pharmaceuticals, Inc. | Polymeric beads for oligonucleotide synthesis |
| AU2005286475A1 (en) | 2004-09-21 | 2006-03-30 | Cytos Biotechnology Ag | Virus-like particles comprising a fusion protein of the coat protein of AP205 and an antigenic polypeptide |
| JP5484732B2 (ja) | 2005-12-14 | 2014-05-07 | サイトス バイオテクノロジー アーゲー | 過敏症の治療のための免疫賦活性核酸パッケージ粒子 |
-
2007
- 2007-12-12 EP EP07865549.5A patent/EP2125854B1/en active Active
- 2007-12-12 CN CN2007800498509A patent/CN101611048B/zh active Active
- 2007-12-12 WO PCT/US2007/087183 patent/WO2008073960A2/en not_active Ceased
- 2007-12-12 CA CA2671873A patent/CA2671873C/en active Active
- 2007-12-12 JP JP2009541546A patent/JP5389662B2/ja active Active
- 2007-12-12 US US11/954,511 patent/US8586728B2/en active Active
- 2007-12-12 AU AU2007333147A patent/AU2007333147B2/en active Active
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2013
- 2013-10-15 US US14/054,068 patent/US20140200338A1/en not_active Abandoned
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2015
- 2015-06-23 US US14/748,045 patent/US9914746B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| US8586728B2 (en) | 2013-11-19 |
| EP2125854A2 (en) | 2009-12-02 |
| WO2008073960A2 (en) | 2008-06-19 |
| US20080139797A1 (en) | 2008-06-12 |
| AU2007333147A1 (en) | 2008-06-19 |
| AU2007333147B2 (en) | 2013-12-19 |
| US20140200338A1 (en) | 2014-07-17 |
| JP2010512169A (ja) | 2010-04-22 |
| CN101611048A (zh) | 2009-12-23 |
| US9914746B2 (en) | 2018-03-13 |
| CA2671873A1 (en) | 2008-06-19 |
| US20160145293A1 (en) | 2016-05-26 |
| JP5389662B2 (ja) | 2014-01-15 |
| EP2125854B1 (en) | 2016-10-26 |
| WO2008073960A3 (en) | 2008-08-07 |
| CN101611048B (zh) | 2012-11-07 |
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| EEER | Examination request | ||
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