JP2017518966A5 - - Google Patents
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- Publication number
- JP2017518966A5 JP2017518966A5 JP2016565175A JP2016565175A JP2017518966A5 JP 2017518966 A5 JP2017518966 A5 JP 2017518966A5 JP 2016565175 A JP2016565175 A JP 2016565175A JP 2016565175 A JP2016565175 A JP 2016565175A JP 2017518966 A5 JP2017518966 A5 JP 2017518966A5
- Authority
- JP
- Japan
- Prior art keywords
- hydrogen
- alkyl
- halogen
- compound
- compound according
- 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
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- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 29
- 229910052739 hydrogen Inorganic materials 0.000 claims 21
- 239000001257 hydrogen Substances 0.000 claims 21
- 238000000034 method Methods 0.000 claims 19
- 150000007523 nucleic acids Chemical class 0.000 claims 18
- 229910052736 halogen Inorganic materials 0.000 claims 17
- 150000002367 halogens Chemical class 0.000 claims 17
- 150000002431 hydrogen Chemical class 0.000 claims 17
- 108020004707 nucleic acids Proteins 0.000 claims 17
- 102000039446 nucleic acids Human genes 0.000 claims 17
- 239000002773 nucleotide Substances 0.000 claims 11
- 125000003729 nucleotide group Chemical group 0.000 claims 11
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical class OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 125000001369 canonical nucleoside group Chemical group 0.000 claims 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000006574 non-aromatic ring group Chemical group 0.000 claims 3
- 102000040430 polynucleotide Human genes 0.000 claims 3
- 108091033319 polynucleotide Proteins 0.000 claims 3
- 239000002157 polynucleotide Substances 0.000 claims 3
- 125000006239 protecting group Chemical group 0.000 claims 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 150000001298 alcohols Chemical class 0.000 claims 2
- 125000001931 aliphatic group Chemical group 0.000 claims 2
- 150000001409 amidines Chemical class 0.000 claims 2
- 125000002619 bicyclic group Chemical group 0.000 claims 2
- 230000008878 coupling Effects 0.000 claims 2
- 238000010168 coupling process Methods 0.000 claims 2
- 238000005859 coupling reaction Methods 0.000 claims 2
- OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 claims 2
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000000178 monomer Substances 0.000 claims 2
- -1 naphthalene alcohol derivatives Chemical class 0.000 claims 2
- 150000002790 naphthalenes Chemical class 0.000 claims 2
- 239000002777 nucleoside Substances 0.000 claims 2
- 150000003833 nucleoside derivatives Chemical class 0.000 claims 2
- 108090000623 proteins and genes Proteins 0.000 claims 2
- 239000007787 solid Substances 0.000 claims 2
- RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical compound CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 claims 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims 1
- OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical group CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 claims 1
- 229930024421 Adenine Natural products 0.000 claims 1
- 229960000643 adenine Drugs 0.000 claims 1
- GFFGJBXGBJISGV-UHFFFAOYSA-N adenyl group Chemical group N1=CN=C2N=CNC2=C1N GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 150000003862 amino acid derivatives Chemical class 0.000 claims 1
- 150000001923 cyclic compounds Chemical class 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 229940104302 cytosine Drugs 0.000 claims 1
- 238000012217 deletion Methods 0.000 claims 1
- 230000037430 deletion Effects 0.000 claims 1
- 239000012351 deprotecting agent Substances 0.000 claims 1
- 125000006575 electron-withdrawing group Chemical group 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 239000007800 oxidant agent Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 claims 1
- 229940113082 thymine Drugs 0.000 claims 1
- 229940035893 uracil Drugs 0.000 claims 1
- 0 B[C@@](C1)O[C@](C*)C1OP(N1CCCC1)O* Chemical compound B[C@@](C1)O[C@](C*)C1OP(N1CCCC1)O* 0.000 description 2
- PHUCBZZSIVNZOW-WUXMJOGZSA-N C/C(/N(C)C)=N\C(NC1=O)=Nc2c1nc[n]2C Chemical compound C/C(/N(C)C)=N\C(NC1=O)=Nc2c1nc[n]2C PHUCBZZSIVNZOW-WUXMJOGZSA-N 0.000 description 1
- IPJLDBQIVAWKND-XFXZXTDPSA-N C/C(/N1CCCC1)=N/C(C=CN1C)=NC1=O Chemical compound C/C(/N1CCCC1)=N/C(C=CN1C)=NC1=O IPJLDBQIVAWKND-XFXZXTDPSA-N 0.000 description 1
- SKINKCWPEUAMFA-XFXZXTDPSA-N C/C(/N1CCOCC1)=N/C(C=CN1C)=NC1=O Chemical compound C/C(/N1CCOCC1)=N/C(C=CN1C)=NC1=O SKINKCWPEUAMFA-XFXZXTDPSA-N 0.000 description 1
- URAHZAPNLSVCME-SXGWCWSVSA-N C/C(/N1CCOCC1)=N/c1ncnc2c1nc[n]2C Chemical compound C/C(/N1CCOCC1)=N/c1ncnc2c1nc[n]2C URAHZAPNLSVCME-SXGWCWSVSA-N 0.000 description 1
- OATAEFUGTOZSCP-RIYZIHGNSA-N C/C(/N1CCOCC1)=N\C(NC1=O)=Nc2c1nc[n]2C Chemical compound C/C(/N1CCOCC1)=N\C(NC1=O)=Nc2c1nc[n]2C OATAEFUGTOZSCP-RIYZIHGNSA-N 0.000 description 1
- FLIOOPBOSTVTGW-SXGWCWSVSA-N CC(C)[n]1c(ncnc2/N=C(/C)\N(C)C)c2nc1 Chemical compound CC(C)[n]1c(ncnc2/N=C(/C)\N(C)C)c2nc1 FLIOOPBOSTVTGW-SXGWCWSVSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201461986594P | 2014-04-30 | 2014-04-30 | |
| US61/986,594 | 2014-04-30 | ||
| PCT/US2015/028624 WO2015168461A2 (en) | 2014-04-30 | 2015-04-30 | Phosphorous protecting groups and methods of preparation and use thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017518966A JP2017518966A (ja) | 2017-07-13 |
| JP2017518966A5 true JP2017518966A5 (enExample) | 2018-06-14 |
| JP6730932B2 JP6730932B2 (ja) | 2020-07-29 |
Family
ID=54354752
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016565175A Active JP6730932B2 (ja) | 2014-04-30 | 2015-04-30 | リン保護基ならびにそれらの調製方法および使用 |
Country Status (6)
| Country | Link |
|---|---|
| US (3) | US10196418B2 (enExample) |
| EP (2) | EP3943500A1 (enExample) |
| JP (1) | JP6730932B2 (enExample) |
| KR (1) | KR102375480B1 (enExample) |
| CN (1) | CN106255697B (enExample) |
| WO (1) | WO2015168461A2 (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106255697B (zh) | 2014-04-30 | 2020-04-28 | 安捷伦科技有限公司 | 磷保护基团及其制备方法和用途 |
| MA43822A (fr) | 2016-03-13 | 2018-11-28 | Wave Life Sciences Ltd | Compositions et procédés de synthèse de phosphoramidite et d'oligonucléotides |
| WO2018098264A1 (en) | 2016-11-23 | 2018-05-31 | Wave Life Sciences Ltd. | Compositions and methods for phosphoramidite and oligonucleotide synthesis |
| AU2018261588A1 (en) | 2017-05-01 | 2019-10-31 | Theravance Biopharma R&D Ip, Llc | Methods of treatment using a JAK inhibitor compound |
| KR102668387B1 (ko) | 2019-02-28 | 2024-05-22 | 후지필름 가부시키가이샤 | 펩타이드 화합물의 제조 방법, 보호기 형성용 시약, 및 축합 다환 방향족 탄화 수소 화합물 |
| CN113490679A (zh) | 2019-02-28 | 2021-10-08 | 富士胶片株式会社 | 肽化合物的制造方法、保护基形成用试药及芳香族杂环化合物 |
| WO2021039935A1 (ja) * | 2019-08-29 | 2021-03-04 | 富士フイルム株式会社 | 核酸化合物の製造方法、及び、核酸化合物 |
| EP3805242A1 (en) * | 2019-10-07 | 2021-04-14 | Sterna Biologicals GmbH & Co. KG | Method for the production of a catalytically active dna molecule having improved activity and its use in a method of treating asthma |
| TW202317550A (zh) | 2021-06-25 | 2023-05-01 | 美商施萬生物製藥研發 Ip有限責任公司 | 作為jak抑制劑之咪唑吲唑化合物 |
| CN113461743B (zh) * | 2021-07-09 | 2023-03-17 | 中国石油大学(华东) | 6-甲硫基乙基嘌呤-2’-脱氧核苷及其制备方法和应用 |
| WO2023069865A1 (en) | 2021-10-15 | 2023-04-27 | Codexis, Inc. | Engineered terminal deoxynucleotidyl transferase variants |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4415732A (en) | 1981-03-27 | 1983-11-15 | University Patents, Inc. | Phosphoramidite compounds and processes |
| JPS6251695A (ja) * | 1985-08-29 | 1987-03-06 | Yuki Gosei Yakuhin Kogyo Kk | ホスホロアミダイト類の合成法 |
| NL8700724A (nl) * | 1987-03-27 | 1988-10-17 | Univ Eindhoven Tech | Poly(deoxyribonucleotiden), farmaceutische samenstellingen, gebruik en bereiding van de poly(deoxyribonucleotiden). |
| US5955591A (en) * | 1993-05-12 | 1999-09-21 | Imbach; Jean-Louis | Phosphotriester oligonucleotides, amidites and method of preparation |
| US5948902A (en) | 1997-11-20 | 1999-09-07 | South Alabama Medical Science Foundation | Antisense oligonucleotides to human serine/threonine protein phosphatase genes |
| US6020475A (en) * | 1998-02-10 | 2000-02-01 | Isis Pharmeuticals, Inc. | Process for the synthesis of oligomeric compounds |
| US6531590B1 (en) * | 1998-04-24 | 2003-03-11 | Isis Pharmaceuticals, Inc. | Processes for the synthesis of oligonucleotide compounds |
| US6274725B1 (en) * | 1998-06-02 | 2001-08-14 | Isis Pharmaceuticals, Inc. | Activators for oligonucleotide synthesis |
| US6222030B1 (en) | 1998-08-03 | 2001-04-24 | Agilent Technologies, Inc. | Solid phase synthesis of oligonucleotides using carbonate protecting groups and alpha-effect nucleophile deprotection |
| EP1176151B1 (en) | 2000-07-28 | 2014-08-20 | Agilent Technologies, Inc. | Synthesis of polynucleotides using combined oxidation/deprotection chemistry |
| US20060178507A1 (en) * | 2004-12-30 | 2006-08-10 | Berry & Associates, Inc. | Fluorous oligonucleotide reagents and affinity purification of oligonucleotides |
| KR20130022437A (ko) * | 2011-08-22 | 2013-03-07 | 삼성전자주식회사 | 광분해성 화합물을 사용한, 비특이적 증폭의 감소를 위한 신규한 ｐｃｒ 방법 |
| JP2015529073A (ja) * | 2012-08-20 | 2015-10-05 | ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア | 生物可逆性基を有するポリヌクレオチド |
| CN106255697B (zh) | 2014-04-30 | 2020-04-28 | 安捷伦科技有限公司 | 磷保护基团及其制备方法和用途 |
-
2015
- 2015-04-30 CN CN201580022581.1A patent/CN106255697B/zh active Active
- 2015-04-30 EP EP21173884.4A patent/EP3943500A1/en active Pending
- 2015-04-30 WO PCT/US2015/028624 patent/WO2015168461A2/en not_active Ceased
- 2015-04-30 EP EP15786514.8A patent/EP3137478B1/en active Active
- 2015-04-30 KR KR1020167033381A patent/KR102375480B1/ko active Active
- 2015-04-30 JP JP2016565175A patent/JP6730932B2/ja active Active
- 2015-04-30 US US14/701,288 patent/US10196418B2/en active Active
-
2018
- 2018-10-29 US US16/173,143 patent/US11104699B2/en active Active
-
2021
- 2021-07-19 US US17/379,288 patent/US11584773B2/en active Active
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