CN112752752A - 一种艾司西酞普兰双羟萘酸盐晶型a 的制备方法 - Google Patents
一种艾司西酞普兰双羟萘酸盐晶型a 的制备方法 Download PDFInfo
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- CN112752752A CN112752752A CN201980062665.6A CN201980062665A CN112752752A CN 112752752 A CN112752752 A CN 112752752A CN 201980062665 A CN201980062665 A CN 201980062665A CN 112752752 A CN112752752 A CN 112752752A
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- China
- Prior art keywords
- pamoate
- escitalopram
- water
- solution
- escitalopram oxalate
- 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.)
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- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 239000013078 crystal Substances 0.000 title claims description 12
- WSEQXVZVJXJVFP-FQEVSTJZSA-N escitalopram Chemical compound C1([C@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WSEQXVZVJXJVFP-FQEVSTJZSA-N 0.000 title abstract description 32
- 229960004341 escitalopram Drugs 0.000 title abstract description 29
- 238000000034 method Methods 0.000 claims abstract description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 33
- KTGRHKOEFSJQNS-BDQAORGHSA-N (1s)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-3h-2-benzofuran-5-carbonitrile;oxalic acid Chemical compound OC(=O)C(O)=O.C1([C@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 KTGRHKOEFSJQNS-BDQAORGHSA-N 0.000 claims description 30
- 229960005086 escitalopram oxalate Drugs 0.000 claims description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 30
- YGLLICRFEVEWOZ-UHFFFAOYSA-L disodium;3-carboxy-1-[(3-carboxy-2-oxidonaphthalen-1-yl)methyl]naphthalen-2-olate Chemical class [Na+].[Na+].C1=CC=C2C(CC3=C4C=CC=CC4=CC(=C3O)C([O-])=O)=C(O)C(C([O-])=O)=CC2=C1 YGLLICRFEVEWOZ-UHFFFAOYSA-L 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 5
- 239000007810 chemical reaction solvent Substances 0.000 claims description 4
- 238000004090 dissolution Methods 0.000 claims description 4
- 239000012046 mixed solvent Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000000243 solution Substances 0.000 description 10
- 238000004128 high performance liquid chromatography Methods 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 7
- 238000005303 weighing Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000005054 agglomeration Methods 0.000 description 6
- 230000002776 aggregation Effects 0.000 description 6
- 239000012065 filter cake Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000011259 mixed solution Substances 0.000 description 5
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 description 1
- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 description 1
- 101000878595 Arabidopsis thaliana Squalene synthase 1 Proteins 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- 238000010268 HPLC based assay Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 230000008275 binding mechanism Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000003001 depressive effect Effects 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 229940124834 selective serotonin reuptake inhibitor Drugs 0.000 description 1
- 239000012896 selective serotonin reuptake inhibitor Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
-
- 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
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
本申请涉及一种艾司西酞普兰双羟萘酸盐((S)‑(+)‑1‑〔3‑(二甲胺基)丙基〕‑1‑(4‑氟苯基)‑1,3‑二氢‑5‑氰基异苯并呋喃双羟萘酸盐)晶型A新的制备方法，所述方法环保，无污染，采用所述方法制得的艾司西酞普兰双羟萘酸盐晶型A纯度高，重复性好。
Description
PCT国内申请，说明书已公开。
Claims (11)
- PCT国内申请，权利要求书已公开。
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2018112126085 | 2018-11-26 | ||
| CN201811212608.5A CN111217777A (zh) | 2018-11-26 | 2018-11-26 | 一种高纯度艾司西酞普兰双羟萘酸盐新的制备工艺 |
| PCT/CN2019/110807 WO2020108117A1 (zh) | 2018-11-26 | 2019-10-12 | 一种艾司西酞普兰双羟萘酸盐晶型a的制备方法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN112752752A true CN112752752A (zh) | 2021-05-04 |
Family
ID=70808536
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201811212608.5A Pending CN111217777A (zh) | 2018-11-26 | 2018-11-26 | 一种高纯度艾司西酞普兰双羟萘酸盐新的制备工艺 |
| CN201980062665.6A Pending CN112752752A (zh) | 2018-11-26 | 2019-10-12 | 一种艾司西酞普兰双羟萘酸盐晶型a 的制备方法 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201811212608.5A Pending CN111217777A (zh) | 2018-11-26 | 2018-11-26 | 一种高纯度艾司西酞普兰双羟萘酸盐新的制备工艺 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US12084425B2 (zh) |
| EP (1) | EP3889143B9 (zh) |
| CN (2) | CN111217777A (zh) |
| WO (1) | WO2020108117A1 (zh) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4943590A (en) * | 1988-06-14 | 1990-07-24 | H. Lundbeck A/S | Pharmaceutically useful (+)-1-(3-dimethylaminopropyl)-1-(4'-fluorophenyl)-1,3-dihydrosobenzofuran-5-carbonitrile and non-toxic acid addition salts thereof |
| CN107311968A (zh) * | 2016-03-31 | 2017-11-03 | 广州市恒诺康医药科技有限公司 | 西酞普兰帕莫酸盐和其结晶形态及其制备方法和用途 |
| CN108976188A (zh) * | 2017-06-05 | 2018-12-11 | 上海奥博生物医药技术有限公司 | 一种艾司西酞普兰双羟萘酸盐新的制备方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102757414B (zh) * | 2011-04-25 | 2014-02-19 | 齐鲁制药有限公司 | 艾司西酞普兰草酸盐的制备方法 |
-
2018
- 2018-11-26 CN CN201811212608.5A patent/CN111217777A/zh active Pending
-
2019
- 2019-10-12 US US17/295,843 patent/US12084425B2/en active Active
- 2019-10-12 CN CN201980062665.6A patent/CN112752752A/zh active Pending
- 2019-10-12 WO PCT/CN2019/110807 patent/WO2020108117A1/zh unknown
- 2019-10-12 EP EP19891658.7A patent/EP3889143B9/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4943590A (en) * | 1988-06-14 | 1990-07-24 | H. Lundbeck A/S | Pharmaceutically useful (+)-1-(3-dimethylaminopropyl)-1-(4'-fluorophenyl)-1,3-dihydrosobenzofuran-5-carbonitrile and non-toxic acid addition salts thereof |
| CN107311968A (zh) * | 2016-03-31 | 2017-11-03 | 广州市恒诺康医药科技有限公司 | 西酞普兰帕莫酸盐和其结晶形态及其制备方法和用途 |
| CN108976188A (zh) * | 2017-06-05 | 2018-12-11 | 上海奥博生物医药技术有限公司 | 一种艾司西酞普兰双羟萘酸盐新的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN111217777A (zh) | 2020-06-02 |
| EP3889143A4 (en) | 2021-10-06 |
| EP3889143B9 (en) | 2022-10-05 |
| WO2020108117A1 (zh) | 2020-06-04 |
| US20210276968A1 (en) | 2021-09-09 |
| EP3889143A1 (en) | 2021-10-06 |
| EP3889143B1 (en) | 2022-06-22 |
| US12084425B2 (en) | 2024-09-10 |
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