JP2018523643A5 - - Google Patents
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- Publication number
- JP2018523643A5 JP2018523643A5 JP2018502203A JP2018502203A JP2018523643A5 JP 2018523643 A5 JP2018523643 A5 JP 2018523643A5 JP 2018502203 A JP2018502203 A JP 2018502203A JP 2018502203 A JP2018502203 A JP 2018502203A JP 2018523643 A5 JP2018523643 A5 JP 2018523643A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- acid
- ester
- salt
- protecting group
- 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
- 238000000034 method Methods 0.000 claims description 65
- 239000002253 acid Substances 0.000 claims description 37
- MBLBDJOUHNCFQT-UHFFFAOYSA-N N-acetyl-D-galactosamine Natural products CC(=O)NC(C=O)C(O)C(O)C(O)CO MBLBDJOUHNCFQT-UHFFFAOYSA-N 0.000 claims description 35
- 150000003839 salts Chemical class 0.000 claims description 32
- -1 GalNAc ester Chemical class 0.000 claims description 31
- OVRNDRQMDRJTHS-KEWYIRBNSA-N N-acetyl-D-galactosamine Chemical compound CC(=O)N[C@H]1C(O)O[C@H](CO)[C@H](O)[C@@H]1O OVRNDRQMDRJTHS-KEWYIRBNSA-N 0.000 claims description 31
- 238000006243 chemical reaction Methods 0.000 claims description 26
- 125000006239 protecting group Chemical group 0.000 claims description 26
- 239000003880 polar aprotic solvent Substances 0.000 claims description 22
- 125000004185 ester group Chemical group 0.000 claims description 20
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 14
- 150000001450 anions Chemical group 0.000 claims description 11
- 239000002585 base Substances 0.000 claims description 10
- 230000008878 coupling Effects 0.000 claims description 9
- 238000010168 coupling process Methods 0.000 claims description 9
- 238000005859 coupling reaction Methods 0.000 claims description 9
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 150000002009 diols Chemical class 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 7
- 239000007822 coupling agent Substances 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- MQAYFGXOFCEZRW-UHFFFAOYSA-N oxane-2-carboxylic acid Chemical compound OC(=O)C1CCCCO1 MQAYFGXOFCEZRW-UHFFFAOYSA-N 0.000 claims description 7
- 238000005897 peptide coupling reaction Methods 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 6
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 6
- 108091034117 Oligonucleotide Proteins 0.000 claims description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 5
- 239000011707 mineral Substances 0.000 claims description 5
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 claims description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 230000003287 optical effect Effects 0.000 claims description 4
- PAQZWJGSJMLPMG-UHFFFAOYSA-N propylphosphonic anhydride Substances CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1 PAQZWJGSJMLPMG-UHFFFAOYSA-N 0.000 claims description 4
- 150000003512 tertiary amines Chemical class 0.000 claims description 4
- 150000003527 tetrahydropyrans Chemical class 0.000 claims description 4
- 150000001768 cations Chemical class 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Natural products NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000002841 Lewis acid Substances 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 239000012190 activator Substances 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 125000006242 amine protecting group Chemical group 0.000 claims description 2
- 235000019445 benzyl alcohol Nutrition 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
- 238000005341 cation exchange Methods 0.000 claims description 2
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- 238000006193 diazotization reaction Methods 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 229960002449 glycine Drugs 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical class CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 238000005984 hydrogenation reaction Methods 0.000 claims description 2
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 2
- 150000007517 lewis acids Chemical class 0.000 claims description 2
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 150000005619 secondary aliphatic amines Chemical class 0.000 claims description 2
- 239000011877 solvent mixture Substances 0.000 claims description 2
- 150000003460 sulfonic acids Chemical class 0.000 claims description 2
- 230000009466 transformation Effects 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 230000001268 conjugating effect Effects 0.000 claims 1
- 0 CC(C)(CCOC(C(C1O*)NC(C)=O)OC(CO*)C1O*)OCCC(C)(C)OCC(O)=O Chemical compound CC(C)(CCOC(C(C1O*)NC(C)=O)OC(CO*)C1O*)OCCC(C)(C)OCC(O)=O 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 2
- 238000002955 isolation Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP15180058.8 | 2015-08-06 | ||
| EP15180058 | 2015-08-06 | ||
| PCT/EP2016/068361 WO2017021385A1 (en) | 2015-08-06 | 2016-08-02 | Processes for the preparation of galnac acid derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018523643A JP2018523643A (ja) | 2018-08-23 |
| JP2018523643A5 true JP2018523643A5 (https=) | 2019-09-19 |
| JP6940477B2 JP6940477B2 (ja) | 2021-09-29 |
Family
ID=54056068
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018502203A Active JP6940477B2 (ja) | 2015-08-06 | 2016-08-02 | ＧａｌＮＡｃ酸誘導体の調製法 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US10597417B2 (https=) |
| EP (1) | EP3331892B1 (https=) |
| JP (1) | JP6940477B2 (https=) |
| KR (1) | KR102579520B1 (https=) |
| CN (1) | CN107709342B (https=) |
| AU (1) | AU2016302697B2 (https=) |
| CA (1) | CA2982825C (https=) |
| ES (1) | ES2744437T3 (https=) |
| HR (1) | HRP20191589T1 (https=) |
| IL (1) | IL256528B (https=) |
| MX (1) | MX369556B (https=) |
| PL (1) | PL3331892T3 (https=) |
| SI (1) | SI3331892T1 (https=) |
| WO (1) | WO2017021385A1 (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018215049A1 (en) | 2017-05-23 | 2018-11-29 | F. Hoffmann-La Roche Ag | Process for galnac oligonucleotide conjugates |
| EP3743116B1 (en) * | 2018-01-26 | 2024-07-10 | F. Hoffmann-La Roche AG | Radiolabelled oligonucleotides and process for their preparation |
| AU2019213004B2 (en) * | 2018-01-29 | 2024-03-07 | F. Hoffmann-La Roche Ag | Process for the preparation of GalNAc oligonucleotide conjugates |
| US11510939B1 (en) | 2019-04-19 | 2022-11-29 | Apellis Pharmaceuticals, Inc. | RNAs for complement inhibition |
| CN113840828B (zh) * | 2019-05-20 | 2024-01-16 | 豪夫迈·罗氏有限公司 | 用于制备GalNAc亚磷酰胺差向异构体的方法 |
| AU2020294935B2 (en) | 2019-06-20 | 2022-11-17 | F. Hoffmann-La Roche Ag | Radiolabeled moem type oligonucleotides and process for their preparation |
| CN110734372B (zh) * | 2019-09-30 | 2024-09-24 | 兰州交通大学 | 一种合成烯丙基脂肪醇聚氧乙烯醚羧酸（apea-9）的方法 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US156917A (en) * | 1874-11-17 | Improvement in car-couplings | ||
| US133170A (en) * | 1872-11-19 | Improvement in wheelbarrows | ||
| US1185198A (en) * | 1912-11-25 | 1916-05-30 | Elliott Co | Tube-cleaning apparatus. |
| JP5004234B2 (ja) * | 2006-11-10 | 2012-08-22 | 独立行政法人産業技術総合研究所 | 膜マイクロドメイン又はコレステロール認識タンパク質検出用高感度分子プローブ |
| KR20110082601A (ko) * | 2008-12-19 | 2011-07-19 | 피너클 파마수티칼스, 인코포레이티드 | 페나조피리딘 화합물 |
| EP3222617B1 (en) * | 2009-03-19 | 2022-07-06 | The Johns Hopkins University | Psma-targeting compounds and uses thereof |
| WO2011053614A1 (en) * | 2009-10-30 | 2011-05-05 | Merck Sharp & Dohme Corp. | Crystalline cdm-nag and methods for producing same |
| DK2539451T3 (da) * | 2010-02-24 | 2016-04-04 | Arrowhead Res Corp | Sammensætninger til målrettet tilførsel af siRNA |
| LT2603513T (lt) * | 2010-08-10 | 2020-05-25 | Takeda Pharmaceutical Company Limited | Heterociklinis junginys ir jo panaudojimas kaip ampa receptoriaus teigiamo alosterinio moduliatoriaus |
| EP2652134B1 (en) * | 2010-12-17 | 2017-03-01 | Arrowhead Pharmaceuticals, Inc. | Galactose cluster-pharmacokinetic modulator targeting moiety for sirna |
| US8501930B2 (en) | 2010-12-17 | 2013-08-06 | Arrowhead Madison Inc. | Peptide-based in vivo siRNA delivery system |
| DK2991656T3 (da) | 2013-05-01 | 2020-03-23 | Ionis Pharmaceuticals Inc | Sammensætninger og fremgangsmåder til modulering af apolipoprotein c-iii-ekspression |
| ES2770667T3 (es) | 2013-06-27 | 2020-07-02 | Roche Innovation Ct Copenhagen As | Oligómeros antisentido y conjugados que se dirigen a PCSK9 |
| KR20160083876A (ko) * | 2013-11-14 | 2016-07-12 | 로슈 이노베이션 센터 코펜하겐 에이/에스 | ApoB 안티센스 접합체 화합물 |
| PT3137605T (pt) | 2014-05-01 | 2020-12-18 | Ionis Pharmaceuticals Inc | Composições e métodos para modulação da expressão de angiopoietina de tipo 3 |
-
2016
- 2016-08-02 CA CA2982825A patent/CA2982825C/en active Active
- 2016-08-02 EP EP16745745.6A patent/EP3331892B1/en active Active
- 2016-08-02 SI SI201630375T patent/SI3331892T1/sl unknown
- 2016-08-02 ES ES16745745T patent/ES2744437T3/es active Active
- 2016-08-02 PL PL16745745T patent/PL3331892T3/pl unknown
- 2016-08-02 HR HRP20191589 patent/HRP20191589T1/hr unknown
- 2016-08-02 WO PCT/EP2016/068361 patent/WO2017021385A1/en not_active Ceased
- 2016-08-02 KR KR1020177036266A patent/KR102579520B1/ko active Active
- 2016-08-02 CN CN201680038736.5A patent/CN107709342B/zh active Active
- 2016-08-02 AU AU2016302697A patent/AU2016302697B2/en active Active
- 2016-08-02 JP JP2018502203A patent/JP6940477B2/ja active Active
- 2016-08-02 MX MX2017015662A patent/MX369556B/es active IP Right Grant
-
2017
- 2017-12-24 IL IL256528A patent/IL256528B/en active IP Right Grant
-
2018
- 2018-02-06 US US15/890,181 patent/US10597417B2/en active Active
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