CA2087818A1 - Oligonucleotide analogs, their preparation and use - Google Patents
Oligonucleotide analogs, their preparation and useInfo
- Publication number
- CA2087818A1 CA2087818A1 CA002087818A CA2087818A CA2087818A1 CA 2087818 A1 CA2087818 A1 CA 2087818A1 CA 002087818 A CA002087818 A CA 002087818A CA 2087818 A CA2087818 A CA 2087818A CA 2087818 A1 CA2087818 A1 CA 2087818A1
- Authority
- CA
- Canada
- Prior art keywords
- aryl
- alkyl
- preparation
- seh
- alkoxy
- 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.)
- Granted
Links
- 108091034117 Oligonucleotide Proteins 0.000 title 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 4
- 229910052717 sulfur Inorganic materials 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 108020004707 nucleic acids Proteins 0.000 abstract 2
- 150000007523 nucleic acids Chemical class 0.000 abstract 2
- 102000039446 nucleic acids Human genes 0.000 abstract 2
- 125000002327 selenol group Chemical group [H][Se]* 0.000 abstract 2
- 108020003215 DNA Probes Proteins 0.000 abstract 1
- 239000003298 DNA probe Substances 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000014509 gene expression Effects 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 238000009396 hybridization Methods 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 230000003834 intracellular effect Effects 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000002773 nucleotide Substances 0.000 abstract 1
- 125000003729 nucleotide group Chemical group 0.000 abstract 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 239000000523 sample Substances 0.000 abstract 1
- 229910052711 selenium Inorganic materials 0.000 abstract 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7088—Compounds having three or more nucleosides or nucleotides
- A61K31/7125—Nucleic acids or oligonucleotides having modified internucleoside linkage, i.e. other than 3'-5' phosphodiesters
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/11—Compounds covalently bound to a solid support
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Epidemiology (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Steroid Compounds (AREA)
Abstract
The invention relates to compounds of the formula I (see formula I) where R1 is H, alkyl, acyl, aryl or a phosphate residue; R2 is H, OH, alkoxy, NH2 or halogen; B is a base customary in nucleotide chemistry; a is O or CH2; n is an integer from 1 to 100; W = O, S or Se; V = O, S or NH; Y = O, S, NH or CH2; Y' = O, S, NH or alkylene; X = OH or SH; U = OH, SH, SeH, alkyl, aryl or amine and Z = OH, SH, SeH, an optionally substituted radical from the group comprising alkyl, aryl, heteroaryl, alkoxy or amino, or a group which favors intracellular uptake or serves as the label of a DNA probe or attacks the target nucleic acid during hybridization, where if Z = OH, SH, CH3 or OC2H5, at least one of the groups X, Y, Y', V or W is not OH or O or R1 is not H; a process for their preparation and their use as inhibitors of gene expression, as probes for detecting nucleic acids and as aids in molecular biology.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4201662 | 1992-01-22 | ||
| DEP4201662.2 | 1992-01-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2087818A1 true CA2087818A1 (en) | 1993-07-23 |
| CA2087818C CA2087818C (en) | 2007-07-10 |
Family
ID=6450030
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002087818A Expired - Lifetime CA2087818C (en) | 1992-01-22 | 1993-01-21 | Oligonucleotide analogs, their preparation and use |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP0552766B1 (en) |
| JP (1) | JP3717081B2 (en) |
| KR (1) | KR930016437A (en) |
| AT (1) | ATE217880T1 (en) |
| AU (1) | AU661365B2 (en) |
| CA (1) | CA2087818C (en) |
| DE (1) | DE59310285D1 (en) |
| DK (1) | DK0552766T3 (en) |
| ES (1) | ES2177532T3 (en) |
| FI (1) | FI115214B (en) |
| HU (1) | HU227794B1 (en) |
| IL (1) | IL104461A (en) |
| NO (1) | NO308215B1 (en) |
| NZ (1) | NZ245720A (en) |
| PL (1) | PL172257B1 (en) |
| PT (1) | PT552766E (en) |
| ZA (1) | ZA93422B (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5674856A (en) * | 1993-01-29 | 1997-10-07 | Sankyo Company, Limited | Modified oligodeoxyribonucleoditides |
| US5874553A (en) * | 1995-03-13 | 1999-02-23 | Hoechst Aktiengesellschaft | Phosphonomonoester nucleic acids, process for their preparation, and their use |
| US6087490A (en) * | 1996-03-23 | 2000-07-11 | Novartis Ag | Dinucleotide and oligonucleotide analogues |
| US6723706B2 (en) | 1997-05-05 | 2004-04-20 | Aventis Pharma Deutschland Gmbh | Modified antisense nucleotides complementary to a section of the human Ha-ras gene |
| US7635769B2 (en) | 2001-07-12 | 2009-12-22 | Sanofi-Aventis Drutschland | Oligoribonucleotide derivatives for specific inhibition of gene expression |
Families Citing this family (48)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5378825A (en) * | 1990-07-27 | 1995-01-03 | Isis Pharmaceuticals, Inc. | Backbone modified oligonucleotide analogs |
| US5646261A (en) * | 1992-01-22 | 1997-07-08 | Hoechst Aktiengesellschaft | 3'-derivatized oligonucleotide analogs with non-nucleotidic groupings, their preparation and use |
| DK0593901T3 (en) | 1992-09-24 | 1997-10-27 | Hoechst Ag | Oligoribonucleotide and ribozyme analogs with terminal 3-3 and 5-5 bonds. |
| EP0602524A1 (en) * | 1992-12-15 | 1994-06-22 | Hoechst Aktiengesellschaft | Chemiluminescence marked sequences and their use in sequence testing |
| US6087491A (en) | 1993-01-08 | 2000-07-11 | Hybridon, Inc. | Extremely high purity oligonucleotides and methods of synthesizing them using dimer blocks |
| KR960700262A (en) * | 1993-01-08 | 1996-01-19 | 다알렌 반스톤 | SYNTHESIS OF DIMMER BLOCKS AND THEIR USE IN ASSEMBLING OLIGONUCLEOTIDES |
| WO1994017093A1 (en) * | 1993-01-25 | 1994-08-04 | Hybridon, Inc. | Oligonucleotide alkylphosphonates and alkylphosphonothioates |
| US5532130A (en) * | 1993-07-20 | 1996-07-02 | Dyad Pharmaceutical Corporation | Methods and compositions for sequence-specific hybridization of RNA by 2'-5' oligonucleotides |
| DE4331670A1 (en) * | 1993-09-17 | 1995-03-23 | Hoechst Ag | Antisense oligonucleotides against HSV-1 and the preparation thereof |
| DE4338704A1 (en) | 1993-11-12 | 1995-05-18 | Hoechst Ag | Stabilized oligonucleotides and their use |
| US6919441B2 (en) | 1994-03-14 | 2005-07-19 | Aventis Pharma Deutschland Gmbh | Polyamide-oligonucleotide derivatives, their preparation and use |
| DE4408528A1 (en) * | 1994-03-14 | 1995-09-28 | Hoechst Ag | Peptide oligonucleotide derivatives, their preparation and use |
| US5599922A (en) * | 1994-03-18 | 1997-02-04 | Lynx Therapeutics, Inc. | Oligonucleotide N3'-P5' phosphoramidates: hybridization and nuclease resistance properties |
| US5726297A (en) * | 1994-03-18 | 1998-03-10 | Lynx Therapeutics, Inc. | Oligodeoxyribonucleotide N3' P5' phosphoramidates |
| JP3482209B2 (en) * | 1994-03-18 | 2003-12-22 | ジェロン・コーポレーション | Oligonucleotides N3 '→ P5' phosphoramidate: synthesis and compounds; hybridization and nuclease resistance properties |
| DE4415370A1 (en) * | 1994-05-02 | 1995-11-09 | Hoechst Ag | Modified oligonucleotides, their preparation and their use |
| US5986076A (en) * | 1994-05-11 | 1999-11-16 | Trustees Of Boston University | Photocleavable agents and conjugates for the detection and isolation of biomolecules |
| US5696248A (en) * | 1994-06-15 | 1997-12-09 | Hoechst Aktiengesellschaft | 3'-modified oligonucleotide derivatives |
| DE4438918A1 (en) * | 1994-11-04 | 1996-05-09 | Hoechst Ag | Modified oligonucleotides, their preparation and their use |
| US6150510A (en) | 1995-11-06 | 2000-11-21 | Aventis Pharma Deutschland Gmbh | Modified oligonucleotides, their preparation and their use |
| DE19502912A1 (en) * | 1995-01-31 | 1996-08-01 | Hoechst Ag | G-Cap Stabilized Oligonucleotides |
| US6326487B1 (en) | 1995-06-05 | 2001-12-04 | Aventis Pharma Deutschland Gmbh | 3 modified oligonucleotide derivatives |
| US5859233A (en) * | 1996-02-21 | 1999-01-12 | Lynx Therapeutics, Inc. | Synthons for synthesis of oligonucleotide N3-P5 phosphoramidates |
| US5684143A (en) * | 1996-02-21 | 1997-11-04 | Lynx Therapeutics, Inc. | Oligo-2'-fluoronucleotide N3'->P5' phosphoramidates |
| ATE267247T1 (en) * | 1996-05-24 | 2004-06-15 | Aventis Pharma Gmbh | REAGENT AND METHOD FOR INHIBITING N-RAS EXPRESSION |
| DE19627898A1 (en) * | 1996-07-11 | 1998-01-15 | Hoechst Ag | Solid phase synthesis of oligonucleotides |
| AU9460898A (en) * | 1997-10-14 | 1999-05-03 | Sankyo Company Limited | Modified oligodeoxyribonucleotides having tggg sequence |
| EP1004661A1 (en) | 1998-11-11 | 2000-05-31 | DALLI-WERKE WÄSCHE- und KÖRPERPFLEGE GmbH & Co. KG | High density granule, method for production thereof, and its use as disintegrant in tablets |
| DE19935303A1 (en) | 1999-07-28 | 2001-02-08 | Aventis Pharma Gmbh | Oligonucleotides to inhibit the expression of human eg5 |
| DE19935302A1 (en) | 1999-07-28 | 2001-02-08 | Aventis Pharma Gmbh | Conjugates and processes for their preparation and their use for the transport of molecules across biological membranes |
| KR20060087531A (en) | 2003-08-28 | 2006-08-02 | 노파르티스 아게 | Interfering rna duplex having blunt-ends and 3'-modifications |
| GB0608838D0 (en) | 2006-05-04 | 2006-06-14 | Novartis Ag | Organic compounds |
| AU2009213147A1 (en) | 2008-02-11 | 2009-08-20 | Rxi Pharmaceuticals Corp. | Modified RNAi polynucleotides and uses thereof |
| WO2010008582A2 (en) | 2008-07-18 | 2010-01-21 | Rxi Pharmaceuticals Corporation | Phagocytic cell drug delivery system |
| US8796443B2 (en) | 2008-09-22 | 2014-08-05 | Rxi Pharmaceuticals Corporation | Reduced size self-delivering RNAi compounds |
| WO2010059226A2 (en) | 2008-11-19 | 2010-05-27 | Rxi Pharmaceuticals Corporation | Inhibition of map4k4 through rnai |
| WO2010090762A1 (en) | 2009-02-04 | 2010-08-12 | Rxi Pharmaceuticals Corporation | Rna duplexes with single stranded phosphorothioate nucleotide regions for additional functionality |
| EP2550001B1 (en) | 2010-03-24 | 2019-05-22 | Phio Pharmaceuticals Corp. | Rna interference in ocular indications |
| WO2011119887A1 (en) | 2010-03-24 | 2011-09-29 | Rxi Pharmaceuticals Corporation | Rna interference in dermal and fibrotic indications |
| RU2615143C2 (en) | 2010-03-24 | 2017-04-04 | Адвирна | Self-delivered rnai compounds of reduced size |
| US10934550B2 (en) | 2013-12-02 | 2021-03-02 | Phio Pharmaceuticals Corp. | Immunotherapy of cancer |
| WO2015125845A1 (en) * | 2014-02-20 | 2015-08-27 | 塩野義製薬株式会社 | Phosphate site modification of nucleic acid containing nitrogen-containing non-aromatic heterocycle |
| US11279934B2 (en) | 2014-04-28 | 2022-03-22 | Phio Pharmaceuticals Corp. | Methods for treating cancer using nucleic acids targeting MDM2 or MYCN |
| JP6836987B2 (en) | 2014-09-05 | 2021-03-03 | フィオ ファーマシューティカルズ コーポレーションＰｈｉｏ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｃｏｒｐ． | Methods for treating aging and skin disorders with nucleic acids targeting TYR or MMP1 |
| CA2991598A1 (en) | 2015-07-06 | 2017-01-12 | Rxi Pharmaceuticals Corporation | Nucleic acid molecules targeting superoxide dismutase 1 (sod1) |
| US10808247B2 (en) | 2015-07-06 | 2020-10-20 | Phio Pharmaceuticals Corp. | Methods for treating neurological disorders using a synergistic small molecule and nucleic acids therapeutic approach |
| CN109563509B (en) | 2015-10-19 | 2022-08-09 | 菲奥医药公司 | Reduced size self-delivering nucleic acid compounds targeting long non-coding RNAs |
| JP7353301B2 (en) | 2018-05-07 | 2023-09-29 | アルニラム ファーマスーティカルズ インコーポレイテッド | Extrahepatic delivery |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3239888A1 (en) * | 1982-10-28 | 1984-05-03 | Hubert Prof. Dr. 2000 Hamburg Köster | METHOD FOR PRODUCING OLIGONUCLEOSIDE PHOSPHONATES |
| US4739044A (en) * | 1985-06-13 | 1988-04-19 | Amgen | Method for derivitization of polynucleotides |
| US4950745A (en) * | 1986-10-30 | 1990-08-21 | Daicel Chemical Industries, Ltd. | Process for synthesis of oligonucleotides and compound for forming polymeric protecting group |
| US4816571A (en) * | 1987-06-04 | 1989-03-28 | Applied Biosystems, Inc. | Chemical capping by phosphitylation during oligonucleotide synthesis |
| DE69033495T2 (en) * | 1989-10-24 | 2000-07-20 | Isis Pharmaceuticals, Inc. | 2'-MODIFIED NUCLEOTIDES |
| US5210015A (en) * | 1990-08-06 | 1993-05-11 | Hoffman-La Roche Inc. | Homogeneous assay system using the nuclease activity of a nucleic acid polymerase |
| GB9021625D0 (en) * | 1990-10-04 | 1990-11-21 | Ici Plc | Synthesis of oligonucleotides |
-
1993
- 1993-01-20 KR KR1019930000675A patent/KR930016437A/en not_active Application Discontinuation
- 1993-01-20 IL IL10446193A patent/IL104461A/en not_active IP Right Cessation
- 1993-01-20 FI FI930220A patent/FI115214B/en not_active IP Right Cessation
- 1993-01-20 NZ NZ245720A patent/NZ245720A/en not_active IP Right Cessation
- 1993-01-21 JP JP00839193A patent/JP3717081B2/en not_active Expired - Lifetime
- 1993-01-21 AT AT93100892T patent/ATE217880T1/en active
- 1993-01-21 ES ES93100892T patent/ES2177532T3/en not_active Expired - Lifetime
- 1993-01-21 DK DK93100892T patent/DK0552766T3/en active
- 1993-01-21 AU AU31910/93A patent/AU661365B2/en not_active Expired
- 1993-01-21 HU HU9300162A patent/HU227794B1/en unknown
- 1993-01-21 ZA ZA93422A patent/ZA93422B/en unknown
- 1993-01-21 EP EP93100892A patent/EP0552766B1/en not_active Expired - Lifetime
- 1993-01-21 CA CA002087818A patent/CA2087818C/en not_active Expired - Lifetime
- 1993-01-21 DE DE59310285T patent/DE59310285D1/en not_active Expired - Lifetime
- 1993-01-21 PT PT93100892T patent/PT552766E/en unknown
- 1993-01-21 NO NO930199A patent/NO308215B1/en not_active IP Right Cessation
- 1993-01-22 PL PL93297515A patent/PL172257B1/en unknown
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5674856A (en) * | 1993-01-29 | 1997-10-07 | Sankyo Company, Limited | Modified oligodeoxyribonucleoditides |
| US5807837A (en) * | 1993-01-29 | 1998-09-15 | Sankyo Company, Limited | Composition and method for the treatment or prophylaxis of viral infections using modified oligodeoxyribonucleotides |
| US5874553A (en) * | 1995-03-13 | 1999-02-23 | Hoechst Aktiengesellschaft | Phosphonomonoester nucleic acids, process for their preparation, and their use |
| US6127346A (en) * | 1995-03-13 | 2000-10-03 | Hoechst Aktiengesellschaft | Phosphonomonoester nucleic acids process for their preparation and their use |
| US6087490A (en) * | 1996-03-23 | 2000-07-11 | Novartis Ag | Dinucleotide and oligonucleotide analogues |
| US6723706B2 (en) | 1997-05-05 | 2004-04-20 | Aventis Pharma Deutschland Gmbh | Modified antisense nucleotides complementary to a section of the human Ha-ras gene |
| US7635769B2 (en) | 2001-07-12 | 2009-12-22 | Sanofi-Aventis Drutschland | Oligoribonucleotide derivatives for specific inhibition of gene expression |
Also Published As
| Publication number | Publication date |
|---|---|
| FI930220A0 (en) | 1993-01-20 |
| PT552766E (en) | 2002-10-31 |
| ES2177532T3 (en) | 2002-12-16 |
| KR930016437A (en) | 1993-08-26 |
| JPH05310779A (en) | 1993-11-22 |
| CA2087818C (en) | 2007-07-10 |
| IL104461A0 (en) | 1993-05-13 |
| FI930220A (en) | 1993-07-23 |
| NZ245720A (en) | 1995-12-21 |
| HUT63173A (en) | 1993-07-28 |
| FI115214B (en) | 2005-03-31 |
| DE59310285D1 (en) | 2002-06-27 |
| IL104461A (en) | 2001-05-20 |
| NO308215B1 (en) | 2000-08-14 |
| AU661365B2 (en) | 1995-07-20 |
| AU3191093A (en) | 1993-07-29 |
| PL172257B1 (en) | 1997-08-29 |
| ATE217880T1 (en) | 2002-06-15 |
| HU9300162D0 (en) | 1993-04-28 |
| ZA93422B (en) | 1993-09-16 |
| JP3717081B2 (en) | 2005-11-16 |
| EP0552766B1 (en) | 2002-05-22 |
| DK0552766T3 (en) | 2002-08-19 |
| EP0552766A2 (en) | 1993-07-28 |
| NO930199L (en) | 1993-07-23 |
| EP0552766A3 (en) | 1994-09-07 |
| PL297515A1 (en) | 1993-09-06 |
| NO930199D0 (en) | 1993-01-21 |
| HU227794B1 (en) | 2012-03-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20130121 |