ZA200504017B - Novel 2',5'-oligoadenylic acid analogues. - Google Patents
Novel 2',5'-oligoadenylic acid analogues. Download PDFInfo
- Publication number
- ZA200504017B ZA200504017B ZA200504017A ZA200504017A ZA200504017B ZA 200504017 B ZA200504017 B ZA 200504017B ZA 200504017 A ZA200504017 A ZA 200504017A ZA 200504017 A ZA200504017 A ZA 200504017A ZA 200504017 B ZA200504017 B ZA 200504017B
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- ZA
- South Africa
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- carbon atoms
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- 239000002253 acid Substances 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims description 54
- SIIZPVYVXNXXQG-KGXOGWRBSA-N [(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-4-[[(3s,4r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-3-hydroxyoxolan-2-yl]methyl [(2r,4r,5r)-2-(6-aminopurin-9-yl)-4-hydroxy-5-(phosphonooxymethyl)oxolan-3-yl] hydrogen phosphate Chemical class C1=NC2=C(N)N=CN=C2N1[C@@H]1O[C@H](COP(O)(=O)OC2[C@@H](O[C@H](COP(O)(O)=O)[C@H]2O)N2C3=NC=NC(N)=C3N=C2)[C@@H](O)[C@H]1OP(O)(=O)OCC([C@@H](O)[C@H]1O)OC1N1C(N=CN=C2N)=C2N=C1 SIIZPVYVXNXXQG-KGXOGWRBSA-N 0.000 claims description 25
- 125000006239 protecting group Chemical group 0.000 claims description 23
- 238000001668 nucleic acid synthesis Methods 0.000 claims description 22
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- 239000000126 substance Substances 0.000 claims description 19
- 125000003277 amino group Chemical group 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 14
- 108091034117 Oligonucleotide Proteins 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 10
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 230000000692 anti-sense effect Effects 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 230000000259 anti-tumor effect Effects 0.000 claims description 5
- 229940079593 drug Drugs 0.000 claims description 5
- 229940041181 antineoplastic drug Drugs 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000004545 purin-9-yl group Chemical group N1=CN=C2N(C=NC2=C1)* 0.000 claims description 4
- 230000000840 anti-viral effect Effects 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- -1 6-aminopurin-9-yl Chemical group 0.000 claims 16
- 239000000203 mixture Substances 0.000 claims 13
- 238000002360 preparation method Methods 0.000 claims 3
- 125000005426 adeninyl group Chemical group N1=C(N=C2N=CNC2=C1N)* 0.000 claims 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims 1
- 239000003443 antiviral agent Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine group Chemical group [C@@H]1([C@H](O)[C@H](O)[C@@H](CO)O1)N1C=NC=2C(N)=NC=NC12 OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 6
- 102100027962 2-5A-dependent ribonuclease Human genes 0.000 description 3
- 108010000834 2-5A-dependent ribonuclease Proteins 0.000 description 3
- 239000002126 C01EB10 - Adenosine Substances 0.000 description 3
- 241000700605 Viruses Species 0.000 description 3
- 229960005305 adenosine Drugs 0.000 description 3
- 230000002155 anti-virotic effect Effects 0.000 description 3
- 239000002246 antineoplastic agent Substances 0.000 description 3
- 108091032973 (ribonucleotides)n+m Proteins 0.000 description 2
- 102000014150 Interferons Human genes 0.000 description 2
- 108010050904 Interferons Proteins 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 239000000074 antisense oligonucleotide Substances 0.000 description 2
- 238000012230 antisense oligonucleotides Methods 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 230000000593 degrading effect Effects 0.000 description 2
- 239000003966 growth inhibitor Substances 0.000 description 2
- 108020004999 messenger RNA Proteins 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 2
- 230000003612 virological effect Effects 0.000 description 2
- 102000040650 (ribonucleotides)n+m Human genes 0.000 description 1
- 108020004463 18S ribosomal RNA Proteins 0.000 description 1
- 102000007445 2',5'-Oligoadenylate Synthetase Human genes 0.000 description 1
- 108010086241 2',5'-Oligoadenylate Synthetase Proteins 0.000 description 1
- 102100036413 2',5'-phosphodiesterase 12 Human genes 0.000 description 1
- 108010035903 2'-phosphodiesterase Proteins 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 102000011727 Caspases Human genes 0.000 description 1
- 108010076667 Caspases Proteins 0.000 description 1
- 102100030497 Cytochrome c Human genes 0.000 description 1
- 108010075031 Cytochromes c Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 238000012404 In vitro experiment Methods 0.000 description 1
- 101710163270 Nuclease Proteins 0.000 description 1
- 206010033128 Ovarian cancer Diseases 0.000 description 1
- 206010061535 Ovarian neoplasm Diseases 0.000 description 1
- 102000004160 Phosphoric Monoester Hydrolases Human genes 0.000 description 1
- 108090000608 Phosphoric Monoester Hydrolases Proteins 0.000 description 1
- 108020000999 Viral RNA Proteins 0.000 description 1
- 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 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000006907 apoptotic process Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229940079322 interferon Drugs 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 150000004712 monophosphates Chemical group 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 239000002777 nucleoside Substances 0.000 description 1
- 150000003833 nucleoside derivatives Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 125000002264 triphosphate group Chemical group [H]OP(=O)(O[H])OP(=O)(O[H])OP(=O)(O[H])O* 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
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- 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
- C12N15/113—Non-coding nucleic acids modulating the expression of genes, e.g. antisense oligonucleotides; Antisense DNA or RNA; Triplex- forming oligonucleotides; Catalytic nucleic acids, e.g. ribozymes; Nucleic acids used in co-suppression or gene silencing
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N2310/00—Structure or type of the nucleic acid
- C12N2310/10—Type of nucleic acid
- C12N2310/11—Antisense
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N2310/00—Structure or type of the nucleic acid
- C12N2310/30—Chemical structure
- C12N2310/31—Chemical structure of the backbone
- C12N2310/315—Phosphorothioates
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N2310/00—Structure or type of the nucleic acid
- C12N2310/30—Chemical structure
- C12N2310/31—Chemical structure of the backbone
- C12N2310/319—Chemical structure of the backbone linked by 2'-5' linkages, i.e. having a free 3'-position
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N2310/00—Structure or type of the nucleic acid
- C12N2310/30—Chemical structure
- C12N2310/32—Chemical structure of the sugar
- C12N2310/321—2'-O-R Modification
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N2310/00—Structure or type of the nucleic acid
- C12N2310/30—Chemical structure
- C12N2310/32—Chemical structure of the sugar
- C12N2310/323—Chemical structure of the sugar modified ring structure
- C12N2310/3231—Chemical structure of the sugar modified ring structure having an additional ring, e.g. LNA, ENA
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N2310/00—Structure or type of the nucleic acid
- C12N2310/30—Chemical structure
- C12N2310/35—Nature of the modification
- C12N2310/351—Conjugate
- C12N2310/3515—Lipophilic moiety, e.g. cholesterol
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Genetics & Genomics (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Biotechnology (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- General Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biophysics (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physics & Mathematics (AREA)
- Medicinal Chemistry (AREA)
- Microbiology (AREA)
- Plant Pathology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Virology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002334731 | 2002-11-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200504017B true ZA200504017B (en) | 2006-02-22 |
Family
ID=32321740
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200504017A ZA200504017B (en) | 2002-11-19 | 2005-05-18 | Novel 2',5'-oligoadenylic acid analogues. |
Country Status (17)
| Country | Link |
|---|---|
| US (2) | US7651999B2 (no) |
| EP (1) | EP1568704A4 (no) |
| KR (1) | KR101117998B1 (no) |
| CN (1) | CN1738829B (no) |
| AU (1) | AU2003284578B2 (no) |
| BR (1) | BR0316431A (no) |
| CA (1) | CA2506581C (no) |
| CO (1) | CO5690648A2 (no) |
| IL (1) | IL168475A (no) |
| MX (1) | MXPA05005321A (no) |
| NO (1) | NO20052975L (no) |
| NZ (1) | NZ539979A (no) |
| PL (1) | PL211566B1 (no) |
| RU (1) | RU2311422C2 (no) |
| TW (1) | TWI347948B (no) |
| WO (1) | WO2004046161A1 (no) |
| ZA (1) | ZA200504017B (no) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20020055479A1 (en) | 2000-01-18 | 2002-05-09 | Cowsert Lex M. | Antisense modulation of PTP1B expression |
| US7179796B2 (en) | 2000-01-18 | 2007-02-20 | Isis Pharmaceuticals, Inc. | Antisense modulation of PTP1B expression |
| TWI347948B (en) * | 2002-11-19 | 2011-09-01 | Sankyo Co | Novel 2',5'-oligoadenylic acid compositions |
| US20050106101A1 (en) * | 2003-10-31 | 2005-05-19 | Ajay Purohit | Novel chemical agents comprising an adenosine moiety or an adenosine analog moiety and an imaging moiety and methods of their use |
| SG162743A1 (en) * | 2005-05-18 | 2010-07-29 | Mitsui Chemicals Inc | Catalyst for olefin polymerization, method for producing olefin polymer, method for producing propylene copolymer, propylene polymer, propylene polymer composition, and use of those |
| AU2008210411A1 (en) * | 2007-01-31 | 2008-08-07 | Alios Biopharma, Inc. | 2-5A derivatives and their use as anti-cancer, anti-viral and anti-parasitic agents |
| US20090181921A1 (en) * | 2007-12-21 | 2009-07-16 | Alios Biopharma Inc. | 2-5a analogs and their methods of use |
| WO2009146417A1 (en) * | 2008-05-30 | 2009-12-03 | Sigma-Aldrich Co. | Compositions and methods for specifically silencing a target nucleic acid |
| EP2697244B1 (en) | 2011-04-13 | 2017-05-17 | Ionis Pharmaceuticals, Inc. | Antisense modulation of ptp1b expression |
| WO2013191129A1 (ja) * | 2012-06-18 | 2013-12-27 | 第一三共株式会社 | ヌクレオシド類縁体の製造中間体及びその製造方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE141796T1 (de) * | 1988-06-09 | 1996-09-15 | Univ Temple | 2',5'-oligoadenylat-derivate zur verwendung als heilmittel |
| JP3781879B2 (ja) | 1996-11-18 | 2006-05-31 | 武 今西 | 新規ヌクレオチド類縁体 |
| JP3756313B2 (ja) | 1997-03-07 | 2006-03-15 | 武 今西 | 新規ビシクロヌクレオシド及びオリゴヌクレオチド類縁体 |
| CZ296576B6 (cs) * | 1999-02-12 | 2006-04-12 | Sankyo Company Limited | Nukleosidový analog a oligonukleotidový analog a farmaceutický prostredek, sonda a primer s jeho obsahem |
| JP2003510281A (ja) * | 1999-09-29 | 2003-03-18 | ザ クリーブランド クリニック ファウンデーション | ２−５ａおよびインターフェロンを用いる治療 |
| JP4245837B2 (ja) * | 2000-12-21 | 2009-04-02 | 第一三共株式会社 | ２’，５’−オリゴアデニル酸類縁体 |
| TWI347948B (en) * | 2002-11-19 | 2011-09-01 | Sankyo Co | Novel 2',5'-oligoadenylic acid compositions |
-
2003
- 2003-11-18 TW TW092132261A patent/TWI347948B/zh not_active IP Right Cessation
- 2003-11-19 MX MXPA05005321A patent/MXPA05005321A/es active IP Right Grant
- 2003-11-19 EP EP03774061A patent/EP1568704A4/en not_active Withdrawn
- 2003-11-19 BR BR0316431-4A patent/BR0316431A/pt not_active IP Right Cessation
- 2003-11-19 WO PCT/JP2003/014748 patent/WO2004046161A1/ja active IP Right Grant
- 2003-11-19 KR KR1020057009011A patent/KR101117998B1/ko not_active IP Right Cessation
- 2003-11-19 CN CN2003801089629A patent/CN1738829B/zh not_active Expired - Fee Related
- 2003-11-19 PL PL376926A patent/PL211566B1/pl not_active IP Right Cessation
- 2003-11-19 AU AU2003284578A patent/AU2003284578B2/en not_active Ceased
- 2003-11-19 CA CA2506581A patent/CA2506581C/en not_active Expired - Fee Related
- 2003-11-19 RU RU2005115129/04A patent/RU2311422C2/ru not_active IP Right Cessation
- 2003-11-19 NZ NZ539979A patent/NZ539979A/en not_active IP Right Cessation
-
2005
- 2005-05-09 IL IL168475A patent/IL168475A/en not_active IP Right Cessation
- 2005-05-16 US US11/131,412 patent/US7651999B2/en not_active Expired - Fee Related
- 2005-05-18 CO CO05048112A patent/CO5690648A2/es unknown
- 2005-05-18 ZA ZA200504017A patent/ZA200504017B/en unknown
- 2005-06-17 NO NO20052975A patent/NO20052975L/no not_active Application Discontinuation
-
2009
- 2009-10-09 US US12/587,608 patent/US7994152B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| NZ539979A (en) | 2007-05-31 |
| TWI347948B (en) | 2011-09-01 |
| US7651999B2 (en) | 2010-01-26 |
| PL376926A1 (pl) | 2006-01-09 |
| US20100035976A1 (en) | 2010-02-11 |
| US7994152B2 (en) | 2011-08-09 |
| CO5690648A2 (es) | 2006-10-31 |
| CN1738829A (zh) | 2006-02-22 |
| WO2004046161A1 (ja) | 2004-06-03 |
| PL211566B1 (pl) | 2012-05-31 |
| AU2003284578B2 (en) | 2007-07-05 |
| NO20052975D0 (no) | 2005-06-17 |
| MXPA05005321A (es) | 2005-07-25 |
| CA2506581C (en) | 2013-05-28 |
| BR0316431A (pt) | 2005-10-11 |
| CA2506581A1 (en) | 2004-06-03 |
| CN1738829B (zh) | 2012-11-28 |
| RU2005115129A (ru) | 2006-02-27 |
| AU2003284578A1 (en) | 2004-06-15 |
| IL168475A (en) | 2010-05-31 |
| RU2311422C2 (ru) | 2007-11-27 |
| US20050261235A1 (en) | 2005-11-24 |
| EP1568704A1 (en) | 2005-08-31 |
| KR20050083891A (ko) | 2005-08-26 |
| KR101117998B1 (ko) | 2012-04-12 |
| TW200416224A (en) | 2004-09-01 |
| NO20052975L (no) | 2005-08-18 |
| EP1568704A4 (en) | 2009-12-02 |
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