ES2569927T3 - Oligonucleótidos inmunomoduladores estabilizados - Google Patents
Oligonucleótidos inmunomoduladores estabilizados Download PDFInfo
- Publication number
- ES2569927T3 ES2569927T3 ES10011770.4T ES10011770T ES2569927T3 ES 2569927 T3 ES2569927 T3 ES 2569927T3 ES 10011770 T ES10011770 T ES 10011770T ES 2569927 T3 ES2569927 T3 ES 2569927T3
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- deoxy
- substituted
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- arabinocytidine
- dna
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- 108091034117 Oligonucleotide Proteins 0.000 title abstract 3
- 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 1
- 230000002519 immonomodulatory effect Effects 0.000 title 1
- UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical group O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 abstract 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 6
- 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 abstract 4
- IQFYYKKMVGJFEH-XLPZGREQSA-N Thymidine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-XLPZGREQSA-N 0.000 abstract 4
- VGONTNSXDCQUGY-UHFFFAOYSA-N desoxyinosine Natural products C1C(O)C(CO)OC1N1C(NC=NC2=O)=C2N=C1 VGONTNSXDCQUGY-UHFFFAOYSA-N 0.000 abstract 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 3
- PHNDUXLWAVSUAL-SHYZEUOFSA-N 1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-sulfanylidenepyrimidin-2-one Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=S)C=C1 PHNDUXLWAVSUAL-SHYZEUOFSA-N 0.000 abstract 2
- UHDGCWIWMRVCDJ-UHFFFAOYSA-N 1-beta-D-Xylofuranosyl-NH-Cytosine Natural products O=C1N=C(N)C=CN1C1C(O)C(O)C(CO)O1 UHDGCWIWMRVCDJ-UHFFFAOYSA-N 0.000 abstract 2
- YKBGVTZYEHREMT-KVQBGUIXSA-N 2'-deoxyguanosine Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1[C@H]1C[C@H](O)[C@@H](CO)O1 YKBGVTZYEHREMT-KVQBGUIXSA-N 0.000 abstract 2
- YKBGVTZYEHREMT-UHFFFAOYSA-N 2'-deoxyguanosine Natural products C1=2NC(N)=NC(=O)C=2N=CN1C1CC(O)C(CO)O1 YKBGVTZYEHREMT-UHFFFAOYSA-N 0.000 abstract 2
- IQFYYKKMVGJFEH-BIIVOSGPSA-N 2'-deoxythymidine Natural products O=C1NC(=O)C(C)=CN1[C@@H]1O[C@@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-BIIVOSGPSA-N 0.000 abstract 2
- CKTSBUTUHBMZGZ-SHYZEUOFSA-N 2'‐deoxycytidine Chemical compound O=C1N=C(N)C=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 CKTSBUTUHBMZGZ-SHYZEUOFSA-N 0.000 abstract 2
- PFCLMNDDPTZJHQ-XLPZGREQSA-N 2-amino-7-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1h-pyrrolo[2,3-d]pyrimidin-4-one Chemical compound C1=CC=2C(=O)NC(N)=NC=2N1[C@H]1C[C@H](O)[C@@H](CO)O1 PFCLMNDDPTZJHQ-XLPZGREQSA-N 0.000 abstract 2
- SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 abstract 2
- CKZJTNZSBMVFSU-UBKIQSJTSA-N 4-amino-5-hydroxy-1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one Chemical compound C1=C(O)C(N)=NC(=O)N1[C@@H]1O[C@H](CO)[C@@H](O)C1 CKZJTNZSBMVFSU-UBKIQSJTSA-N 0.000 abstract 2
- 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 abstract 2
- UHDGCWIWMRVCDJ-PSQAKQOGSA-N Cytidine Natural products O=C1N=C(N)C=CN1[C@@H]1[C@@H](O)[C@@H](O)[C@H](CO)O1 UHDGCWIWMRVCDJ-PSQAKQOGSA-N 0.000 abstract 2
- NYHBQMYGNKIUIF-UHFFFAOYSA-N D-guanosine Natural products C1=2NC(N)=NC(=O)C=2N=CN1C1OC(CO)C(O)C1O NYHBQMYGNKIUIF-UHFFFAOYSA-N 0.000 abstract 2
- CKTSBUTUHBMZGZ-UHFFFAOYSA-N Deoxycytidine Natural products O=C1N=C(N)C=CN1C1OC(CO)C(O)C1 CKTSBUTUHBMZGZ-UHFFFAOYSA-N 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- IQFYYKKMVGJFEH-UHFFFAOYSA-N beta-L-thymidine Natural products O=C1NC(=O)C(C)=CN1C1OC(CO)C(O)C1 IQFYYKKMVGJFEH-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- UHDGCWIWMRVCDJ-ZAKLUEHWSA-N cytidine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O1 UHDGCWIWMRVCDJ-ZAKLUEHWSA-N 0.000 abstract 2
- NAGJZTKCGNOGPW-UHFFFAOYSA-K dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [O-]P([O-])([S-])=S NAGJZTKCGNOGPW-UHFFFAOYSA-K 0.000 abstract 2
- 229940029575 guanosine Drugs 0.000 abstract 2
- 150000004713 phosphodiesters Chemical class 0.000 abstract 2
- 150000003834 purine nucleoside derivatives Chemical class 0.000 abstract 2
- 239000002718 pyrimidine nucleoside Substances 0.000 abstract 2
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 abstract 2
- VGONTNSXDCQUGY-RRKCRQDMSA-N 2'-deoxyinosine Chemical group C1[C@H](O)[C@@H](CO)O[C@H]1N1C(N=CNC2=O)=C2N=C1 VGONTNSXDCQUGY-RRKCRQDMSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 1
- 229930195729 fatty acid Natural products 0.000 abstract 1
- 239000000194 fatty acid Substances 0.000 abstract 1
- 150000004665 fatty acids Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 230000003308 immunostimulating effect Effects 0.000 abstract 1
- 150000002632 lipids Chemical class 0.000 abstract 1
- 108020004707 nucleic acids Proteins 0.000 abstract 1
- 150000007523 nucleic acids Chemical class 0.000 abstract 1
- 102000039446 nucleic acids Human genes 0.000 abstract 1
- 239000002777 nucleoside Substances 0.000 abstract 1
- 108090000765 processed proteins & peptides Proteins 0.000 abstract 1
- 150000003230 pyrimidines Chemical class 0.000 abstract 1
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- C12N15/00—Mutation or genetic engineering; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification; Use of hosts therefor
- C12N15/09—Recombinant DNA-technology
- C12N15/11—DNA or RNA fragments; Modified forms thereof; Non-coding nucleic acids having a biological activity
- C12N15/117—Nucleic acids having immunomodulatory properties, e.g. containing CpG-motifs
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- 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
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
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- 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
- C07H21/04—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 deoxyribosyl as saccharide radical
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- C12N2310/00—Structure or type of the nucleic acid
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- C12N2310/17—Immunomodulatory nucleic acids
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- C12N2310/30—Chemical structure
- C12N2310/31—Chemical structure of the backbone
- C12N2310/318—Chemical structure of the backbone where the PO2 is completely replaced, e.g. MMI or formacetal
- C12N2310/3183—Diol linkers, e.g. glycols or propanediols
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Abstract
Un ácido nucleico inmunoestimulador que tiene una estructura secundaria formada por un enlace de hidrógeno intermolecular entre dos compuestos oligonucleótidos, en donde los dos compuestos oligonucleótidos comprenden la estructura general de: Dominio A-Dominio B-Dominio C (I) en donde el dominio A es ADN 5'-3', ARN-ADN, ADN-ARN que tiene un dominio palindrómico o autocomplementario, o no lo tiene, y que contiene un dinucleótido, o no lo contiene, seleccionado entre el grupo que consiste en CpG, C*pG, C*pG* y CpG*, en donde C es citidina o 2'-desoxicitidina, G es guanosina o 2' desoxiguanosina, C* es 2'-desoxitimidina, 1-(2'-desoxi-ß-D-ribofuranosilo)-2-oxo-7- deaza-8-metil-purina, 2'-didesoxi-5-halocitosina, 2'-didesoxi-5-nitrocitosina, arabinocitidina, arabinocitidina sustituida en 2'-desoxi-2', arabinocitidina sustituida en 2'-O, 2'-desoxi-5-hidroxicitidina, 2'- desoxi-N4-alquil-citidina, 2'-desoxi-4-tiouridina, u otros análogos de nucleósidos de pirimidina, G* es 2' desoxi-7-deazaguanosina, 2'-desoxi-6-tioguanosina, arabinoguanosina, arabinoguanosina sustituida en 2'-desoxi-2', arabinoguanosina sustituida en 2'-O, 2'- desoxiinosina, u otros análogos de nucleósidos de purina y p es un enlace internucleósido seleccionado entre el grupo que consiste en fosfodiéster, fosforotioato, y fosforoditioato, el dominio B es un enlazador no nucleósido que une los dominios A y C que puede ser alifático, aromático, arilo, cíclico, quiral, aquiral, un péptido, un hidrato de carbono, un lípido, un ácido graso, monopolietilenglicol, tripolientilenglicol o hexapolietilenglicol, o un resto heterocíclico, y el dominio C es ADN 3'-5', ARN-ADN, ADN-ARN que tiene una secuencia palindrómica o autocomplementaria, o no la tiene, y que contiene un dinucleótido, o no lo contiene, seleccionado entre el grupo que consiste en CpG, C*pG, C*pG* y CpG*, en donde C es citidina o 2'-desoxicitidina, G es guanosina o 2' desoxiguanosina, C* es 2'-desoxitimidina, 1-(2'-desoxi-ß-D-ribofuranosilo)-2-oxo-7- deaza-8-metil-purina, 2'-didesoxi-5-halocitosina, 2'-didesoxi-5-nitrocitosina, arabinocitidina, arabinocitidina sustituida en 2'-desoxi-2', arabinocitidina sustituida en 2'-O, 2'-desoxi-5-hidroxicitidina, 2'- desoxi-N4-alquil-citidina, 2'-desoxi-4-tiouridina, u otros análogos de nucleósidos de pirimidina, G* es 2' desoxi-7-deazaguanosina, 2'-desoxi-6-tioguanosina, arabinoguanosina, arabinoguanosina sustituida en 2'-desoxi-2', arabinoguanosina sustituida en 2'-O, 2'- desoxiinosina, u otros análogos de nucleósidos de purina y p es un enlace internucleósido seleccionado entre el grupo que consiste en fosfodiéster, fosforotioato, y fosforoditioato.
Description
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Applications Claiming Priority (6)
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| US50427903P | 2003-09-18 | 2003-09-18 | |
| US504279P | 2003-09-18 |
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| EP (2) | EP1631576A4 (es) |
| JP (2) | JP4874801B2 (es) |
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| CN (1) | CN102604957B (es) |
| AU (2) | AU2004252505B2 (es) |
| CA (1) | CA2528597C (es) |
| ES (1) | ES2569927T3 (es) |
| MX (1) | MXPA05013658A (es) |
| WO (1) | WO2005001055A2 (es) |
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- 2004-06-10 JP JP2006533760A patent/JP4874801B2/ja not_active Expired - Fee Related
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| Publication number | Publication date |
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| AU2004252505A2 (en) | 2005-01-06 |
| KR101137572B1 (ko) | 2012-05-30 |
| JP4874801B2 (ja) | 2012-02-15 |
| CA2528597A1 (en) | 2005-01-06 |
| CN102604957B (zh) | 2015-10-07 |
| CA2528597C (en) | 2014-08-05 |
| MXPA05013658A (es) | 2006-03-02 |
| KR20060007444A (ko) | 2006-01-24 |
| JP2007500018A (ja) | 2007-01-11 |
| AU2004252505B2 (en) | 2010-10-28 |
| WO2005001055A2 (en) | 2005-01-06 |
| EP1631576A4 (en) | 2010-08-25 |
| US20050026861A1 (en) | 2005-02-03 |
| AU2011200272A1 (en) | 2011-02-17 |
| EP2371834A1 (en) | 2011-10-05 |
| JP2011200248A (ja) | 2011-10-13 |
| EP2371834B1 (en) | 2016-02-17 |
| AU2004252505A1 (en) | 2005-01-06 |
| CN102604957A (zh) | 2012-07-25 |
| US8946175B1 (en) | 2015-02-03 |
| AU2011200272B2 (en) | 2011-12-22 |
| WO2005001055A3 (en) | 2005-10-13 |
| EP1631576A2 (en) | 2006-03-08 |
| US8008267B2 (en) | 2011-08-30 |
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