JPWO2020239568A5 - - Google Patents
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- Publication number
- JPWO2020239568A5 JPWO2020239568A5 JP2021569359A JP2021569359A JPWO2020239568A5 JP WO2020239568 A5 JPWO2020239568 A5 JP WO2020239568A5 JP 2021569359 A JP2021569359 A JP 2021569359A JP 2021569359 A JP2021569359 A JP 2021569359A JP WO2020239568 A5 JPWO2020239568 A5 JP WO2020239568A5
- Authority
- JP
- Japan
- Prior art keywords
- etoh
- methanesulfonylphenoxy
- fluoro
- propyl
- ethyl
- 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.)
- Pending
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Description
[2-(3-フルオロ-5-メタンスルホニルフェノキシ)エチル](プロピル)アミンヘミ-L-酒石酸塩の合成:
実施例2からの[2-(3-フルオロ-5-メタンスルホニルフェノキシ)エチル](プロピル)アミンのEtOH溶液(推定量:24.5g、88.9mmol)を、濃度が0.40MになるまでEtOHで希釈した。水(20mL)中のL-酒石酸(6.81g、45.4mmol)の溶液を添加した。形成されたスラリーを、還流温度に加熱し、追加量のEtOH(50mL)および水(5mL)を添加した。固体がすべて溶解するまで加熱を続けた。混合物を室温に冷却させた後、形成されたスラリーを室温で一晩、次いで5~10℃で5時間撹拌した。沈殿物を濾過により単離し、濾過ケーキをEtOH(3×35mL)で洗浄した。生成物を、そこから空気を抜くことで20分間乾燥した。99.9%のLC純度を有する固体として29.9g(96%)の[2-(3-フルオロ-5-メタンスルホニルフェノキシ)エチル](プロピル)アミンヘミ-L-酒石酸塩を得た。1H NMR(400MHz,DMSO-d6):δ 0.89(t,3H),1.55(m,2H),2.74(t,2H),3.13(t,2H),3.28(s,3H),3.89(s,1H),4.27(t,2H),7.25(m,1H),7.3-7.4(m,2H)。
Synthesis of [2-(3-fluoro-5-methanesulfonylphenoxy)ethyl](propyl)amine hemi-L-tartrate:
A solution of [2-(3-fluoro-5-methanesulfonylphenoxy)ethyl](propyl)amine from Example 2 in EtOH (assumed: 24.5 g, 88.9 mmol) was added to a concentration of 0.40 M. Diluted with EtOH. A solution of L-tartaric acid (6.81 g, 45.4 mmol) in water (20 mL) was added. The slurry formed was heated to reflux and additional EtOH (50 mL) and water (5 mL) were added. Heating was continued until all solids dissolved. After allowing the mixture to cool to room temperature, the slurry formed was stirred at room temperature overnight and then at 5-10° C. for 5 hours. The precipitate was isolated by filtration and the filter cake was washed with EtOH (3 x 35 mL). The product was dried for 20 minutes by removing air from it. Obtained 29.9 g (96%) of [2-(3-fluoro-5-methanesulfonylphenoxy)ethyl](propyl)amine hemi-L-tartrate as a solid with an LC purity of 99.9%. 1 H NMR (400 MHz, DMSO-d 6 ): δ 0.89 (t, 3H), 1.55 (m, 2H), 2.74 (t, 2H), 3.13 (t, 2H), 3 .28 (s, 3H), 3.89 (s, 1H), 4.27 (t, 2H), 7.25 (m, 1H), 7.3-7.4 (m, 2H).
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP19176514.8 | 2019-05-24 | ||
EP19176514 | 2019-05-24 | ||
EP20166361.4 | 2020-03-27 | ||
EP20166361 | 2020-03-27 | ||
PCT/EP2020/064046 WO2020239568A1 (en) | 2019-05-24 | 2020-05-20 | Pharmaceutically acceptable salts of [2-(3-fluoro-5-methane-sulfonylphenoxy)ethyl](propyl)amine and uses thereof |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2022533433A JP2022533433A (en) | 2022-07-22 |
JPWO2020239568A5 true JPWO2020239568A5 (en) | 2023-05-29 |
Family
ID=70682855
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2021569359A Pending JP2022533433A (en) | 2019-05-24 | 2020-05-20 | Pharmaceutically acceptable salts of [2-(3-fluoro-5-methanesulfonylphenoxy)ethyl](propyl)amine and uses thereof |
Country Status (20)
Country | Link |
---|---|
US (1) | US20220267262A1 (en) |
EP (2) | EP4292653A3 (en) |
JP (1) | JP2022533433A (en) |
KR (1) | KR20220011638A (en) |
CN (1) | CN113853369A (en) |
AU (1) | AU2020286003A1 (en) |
BR (1) | BR112021023563A2 (en) |
CA (1) | CA3140805A1 (en) |
CL (1) | CL2021003115A1 (en) |
CO (1) | CO2021016556A2 (en) |
DK (1) | DK3976581T3 (en) |
ES (1) | ES2970361T3 (en) |
FI (1) | FI3976581T3 (en) |
IL (1) | IL288271A (en) |
JO (1) | JOP20210312A1 (en) |
MX (1) | MX2021014271A (en) |
PL (1) | PL3976581T3 (en) |
PT (1) | PT3976581T (en) |
SG (1) | SG11202112165QA (en) |
WO (1) | WO2020239568A1 (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20220168242A1 (en) * | 2020-11-10 | 2022-06-02 | Susanna Holm Waters | Pharmaceutically acceptable salts of mesdopetam and uses thereof |
WO2024042540A1 (en) * | 2022-08-24 | 2024-02-29 | Alkem Laboratories Limited | Mesdopetam compositions |
WO2024062344A1 (en) | 2022-09-21 | 2024-03-28 | Assia Chemical Industries Ltd. | Solid state forms of mesdopetam and salts therof |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SE9904723D0 (en) * | 1999-12-22 | 1999-12-22 | Carlsson A Research Ab | New modulators of dopamine neurotransmission II |
MX2007015606A (en) | 2005-06-23 | 2008-02-25 | Astrazeneca Ab | New azetidine derivatives as neurokinin receptor antagonists for the treatment of gastrointestinal diseases. |
EP2155668A2 (en) * | 2007-06-08 | 2010-02-24 | Arena Pharmaceuticals, Inc. | Crystalline forms of (r)-1-{2-ý4'- (3-methoxy-propane-1- sulfonyl)-biphenyl-4-yl¨-ethyl}-2-methyl-pyrrolidine, and compositions, and methods related thereto |
TW200932225A (en) * | 2007-12-14 | 2009-08-01 | Lundbeck & Co As H | 4-[2,3-difluoro-6-(2-fluoro-4-methyl-phenylsulfanyl)-phenyl]-piperidine |
EP2699543B1 (en) | 2011-04-19 | 2016-03-02 | Integrative Research Laboratories Sweden AB | Novel modulators of cortical dopaminergic- and nmda-receptor-mediated glutamatergic neurotransmission |
AU2018313049B2 (en) * | 2017-08-07 | 2020-07-09 | Suven Life Sciences Limited | Fluoropiperidine compounds as pure 5-HT6 receptor antagonists |
-
2020
- 2020-05-20 FI FIEP20725728.8T patent/FI3976581T3/en active
- 2020-05-20 AU AU2020286003A patent/AU2020286003A1/en active Pending
- 2020-05-20 ES ES20725728T patent/ES2970361T3/en active Active
- 2020-05-20 KR KR1020217037818A patent/KR20220011638A/en unknown
- 2020-05-20 JP JP2021569359A patent/JP2022533433A/en active Pending
- 2020-05-20 SG SG11202112165QA patent/SG11202112165QA/en unknown
- 2020-05-20 PT PT207257288T patent/PT3976581T/en unknown
- 2020-05-20 DK DK20725728.8T patent/DK3976581T3/en active
- 2020-05-20 CA CA3140805A patent/CA3140805A1/en active Pending
- 2020-05-20 BR BR112021023563A patent/BR112021023563A2/en unknown
- 2020-05-20 CN CN202080036829.0A patent/CN113853369A/en active Pending
- 2020-05-20 JO JOP/2021/0312A patent/JOP20210312A1/en unknown
- 2020-05-20 US US17/612,902 patent/US20220267262A1/en active Pending
- 2020-05-20 EP EP23190702.3A patent/EP4292653A3/en active Pending
- 2020-05-20 MX MX2021014271A patent/MX2021014271A/en unknown
- 2020-05-20 WO PCT/EP2020/064046 patent/WO2020239568A1/en unknown
- 2020-05-20 EP EP20725728.8A patent/EP3976581B1/en active Active
- 2020-05-20 PL PL20725728.8T patent/PL3976581T3/en unknown
-
2021
- 2021-11-21 IL IL288271A patent/IL288271A/en unknown
- 2021-11-24 CL CL2021003115A patent/CL2021003115A1/en unknown
- 2021-12-06 CO CONC2021/0016556A patent/CO2021016556A2/en unknown
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