AU2021247043A1 - Synthesis of oligonucleotides and related compounds - Google Patents
Synthesis of oligonucleotides and related compounds Download PDFInfo
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- AU2021247043A1 AU2021247043A1 AU2021247043A AU2021247043A AU2021247043A1 AU 2021247043 A1 AU2021247043 A1 AU 2021247043A1 AU 2021247043 A AU2021247043 A AU 2021247043A AU 2021247043 A AU2021247043 A AU 2021247043A AU 2021247043 A1 AU2021247043 A1 AU 2021247043A1
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- 108091034117 Oligonucleotide Proteins 0.000 title claims abstract description 72
- 150000001875 compounds Chemical class 0.000 title claims description 92
- 238000003786 synthesis reaction Methods 0.000 title abstract description 66
- 230000015572 biosynthetic process Effects 0.000 title abstract description 64
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- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 2
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 102
- 239000000243 solution Substances 0.000 description 99
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 26
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- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 24
- 238000001914 filtration Methods 0.000 description 24
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- 239000000203 mixture Substances 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
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- 125000001072 heteroaryl group Chemical group 0.000 description 15
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
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- 239000000539 dimer Substances 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- 235000000346 sugar Nutrition 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 229910052786 argon Inorganic materials 0.000 description 12
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 12
- 238000010511 deprotection reaction Methods 0.000 description 11
- 238000000746 purification Methods 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 10
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
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- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
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- 125000000753 cycloalkyl group Chemical group 0.000 description 8
- OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 description 8
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- 238000002515 oligonucleotide synthesis Methods 0.000 description 7
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Classifications
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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
-
- 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
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/06—Pyrimidine radicals
- C07H19/067—Pyrimidine radicals with ribosyl as the saccharide radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals
- C07H19/167—Purine radicals with ribosyl as the saccharide radical
-
- 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
-
- 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
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- 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)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Saccharide Compounds (AREA)
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| US202063003067P | 2020-03-31 | 2020-03-31 | |
| US63/003,067 | 2020-03-31 | ||
| PCT/IB2021/052595 WO2021198883A1 (en) | 2020-03-31 | 2021-03-30 | Synthesis of oligonucleotides and related compounds |
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| AU2021247043A1 true AU2021247043A1 (en) | 2022-10-27 |
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| AU2021247043A Abandoned AU2021247043A1 (en) | 2020-03-31 | 2021-03-30 | Synthesis of oligonucleotides and related compounds |
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| EP4293035A4 (en) | 2021-02-12 | 2025-03-05 | Ajinomoto Co., Inc. | METHOD FOR THE PRODUCTION OF OLIGONUCLEOTIDES |
| EP4601656A1 (en) * | 2022-10-12 | 2025-08-20 | Pharmorage Pty Limited | Modified oligonucleotides |
| WO2025028656A1 (ja) | 2023-08-02 | 2025-02-06 | 日東電工株式会社 | オリゴヌクレオチドを製造する方法 |
| WO2025235761A1 (en) * | 2024-05-09 | 2025-11-13 | Biogen Ma Inc. | Reagents and processes for preparing oligonucleotides |
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| WO1992001704A1 (en) | 1990-07-26 | 1992-02-06 | Koichi Shudo | Oligodeoxyribonucleotides |
| US6972330B2 (en) * | 1996-02-13 | 2005-12-06 | Sirna Therapeutics, Inc. | Chemical synthesis of methoxy nucleosides |
| US5753789A (en) | 1996-07-26 | 1998-05-19 | Yale University | Oligonucleotides containing L-nucleosides |
| ES2192672T3 (es) | 1996-11-18 | 2003-10-16 | Takeshi Imanishi | Nuevos analogos de nucleotidos. |
| US6770748B2 (en) | 1997-03-07 | 2004-08-03 | Takeshi Imanishi | Bicyclonucleoside and oligonucleotide analogue |
| 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 |
| US6251666B1 (en) | 1997-03-31 | 2001-06-26 | Ribozyme Pharmaceuticals, Inc. | Nucleic acid catalysts comprising L-nucleotide analogs |
| US6794499B2 (en) | 1997-09-12 | 2004-09-21 | Exiqon A/S | Oligonucleotide analogues |
| JP4236812B2 (ja) | 1997-09-12 | 2009-03-11 | エクシコン エ／エス | オリゴヌクレオチド類似体 |
| ES2234563T5 (es) | 1999-02-12 | 2018-01-17 | Daiichi Sankyo Company, Limited | Nuevos análogos de nucleósidos y oligonucleótidos |
| JP2000247940A (ja) * | 1999-02-26 | 2000-09-12 | Sankyo Co Ltd | 新規ベンジルアジド化合物 |
| US7084125B2 (en) | 1999-03-18 | 2006-08-01 | Exiqon A/S | Xylo-LNA analogues |
| US7053207B2 (en) | 1999-05-04 | 2006-05-30 | Exiqon A/S | L-ribo-LNA analogues |
| US6525191B1 (en) | 1999-05-11 | 2003-02-25 | Kanda S. Ramasamy | Conformationally constrained L-nucleosides |
| JP4151751B2 (ja) | 1999-07-22 | 2008-09-17 | 第一三共株式会社 | 新規ビシクロヌクレオシド類縁体 |
| US7569575B2 (en) | 2002-05-08 | 2009-08-04 | Santaris Pharma A/S | Synthesis of locked nucleic acid derivatives |
| WO2004041889A2 (en) | 2002-11-05 | 2004-05-21 | Isis Pharmaceuticals, Inc. | Polycyclic sugar surrogate-containing oligomeric compounds and compositions for use in gene modulation |
| CN101684136A (zh) * | 2008-09-23 | 2010-03-31 | 苏州瑞博生物技术有限公司 | 一种寡核苷酸的制备方法 |
| US9284344B2 (en) | 2012-05-30 | 2016-03-15 | Hokkaido System Science Co., Ltd. | Oligonucleotide synthesis method using highly dispersible liquid-phase support |
| US10214555B2 (en) | 2012-11-14 | 2019-02-26 | Takeda Pharmaceutical Company Limitjed | Method for liquid-phase synthesis of nucleic acid |
| CN116063365A (zh) | 2015-12-16 | 2023-05-05 | 味之素株式会社 | 寡核苷酸的制备方法以及核苷、核苷酸或寡核苷酸 |
| WO2017111137A1 (ja) | 2015-12-22 | 2017-06-29 | 味の素株式会社 | オリゴヌクレオチドの製造方法 |
| TW201906855A (zh) | 2017-05-02 | 2019-02-16 | 日商日產化學工業股份有限公司 | 寡核苷酸之製造方法 |
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- 2021-03-30 AU AU2021247043A patent/AU2021247043A1/en not_active Abandoned
- 2021-03-30 CA CA3178892A patent/CA3178892A1/en active Pending
- 2021-03-30 CN CN202180039628.0A patent/CN115843299A/zh active Pending
- 2021-03-30 KR KR1020227037806A patent/KR20220161436A/ko active Pending
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- 2021-03-30 BR BR112022019752A patent/BR112022019752A2/pt unknown
- 2021-03-30 IL IL296862A patent/IL296862A/en unknown
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| CN115843299A (zh) | 2023-03-24 |
| BR112022019752A2 (pt) | 2022-11-16 |
| IL296862A (en) | 2022-11-01 |
| WO2021198883A1 (en) | 2021-10-07 |
| KR20220161436A (ko) | 2022-12-06 |
| JP2023520201A (ja) | 2023-05-16 |
| CA3178892A1 (en) | 2021-10-07 |
| US20240092821A1 (en) | 2024-03-21 |
| MX2022012255A (es) | 2023-01-11 |
| EP4126894A1 (en) | 2023-02-08 |
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