CN105218482A - 沃替西汀氢溴酸盐β晶型的制备方法 - Google Patents
沃替西汀氢溴酸盐β晶型的制备方法 Download PDFInfo
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- CN105218482A CN105218482A CN201410287338.XA CN201410287338A CN105218482A CN 105218482 A CN105218482 A CN 105218482A CN 201410287338 A CN201410287338 A CN 201410287338A CN 105218482 A CN105218482 A CN 105218482A
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- 239000013078 crystal Substances 0.000 title claims abstract description 50
- 238000002360 preparation method Methods 0.000 title claims abstract description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000003960 organic solvent Substances 0.000 claims abstract description 23
- 229960000935 dehydrated alcohol Drugs 0.000 claims abstract description 16
- 239000002002 slurry Substances 0.000 claims abstract description 16
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000012065 filter cake Substances 0.000 claims abstract description 14
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 13
- 238000005406 washing Methods 0.000 claims abstract description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000003756 stirring Methods 0.000 claims abstract description 8
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims abstract description 7
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims abstract description 7
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims abstract description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims abstract description 6
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims abstract description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims abstract description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims abstract description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims abstract description 3
- 238000001035 drying Methods 0.000 claims abstract description 3
- 238000007605 air drying Methods 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 239000012453 solvate Substances 0.000 abstract description 7
- 230000002349 favourable effect Effects 0.000 abstract description 3
- 238000001914 filtration Methods 0.000 abstract description 3
- 230000009286 beneficial effect Effects 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 23
- 239000000047 product Substances 0.000 description 11
- 238000000634 powder X-ray diffraction Methods 0.000 description 8
- OAKURXIZZOAYBC-UHFFFAOYSA-M 3-oxopropanoate Chemical compound [O-]C(=O)CC=O OAKURXIZZOAYBC-UHFFFAOYSA-M 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000000935 antidepressant agent Substances 0.000 description 3
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- 102000019208 Serotonin Plasma Membrane Transport Proteins Human genes 0.000 description 2
- 108010012996 Serotonin Plasma Membrane Transport Proteins Proteins 0.000 description 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
- GGRLKHMFMUXIOG-UHFFFAOYSA-M 2-acetyloxyethyl(trimethyl)azanium;hydroxide Chemical compound [OH-].CC(=O)OCC[N+](C)(C)C GGRLKHMFMUXIOG-UHFFFAOYSA-M 0.000 description 1
- 108091005477 5-HT3 receptors Proteins 0.000 description 1
- 108091005436 5-HT7 receptors Proteins 0.000 description 1
- 102100022738 5-hydroxytryptamine receptor 1A Human genes 0.000 description 1
- 101710138638 5-hydroxytryptamine receptor 1A Proteins 0.000 description 1
- 102100027499 5-hydroxytryptamine receptor 1B Human genes 0.000 description 1
- 101710138639 5-hydroxytryptamine receptor 1B Proteins 0.000 description 1
- CTENFNNZBMHDDG-UHFFFAOYSA-N Dopamine hydrochloride Chemical compound Cl.NCCC1=CC=C(O)C(O)=C1 CTENFNNZBMHDDG-UHFFFAOYSA-N 0.000 description 1
- 229960002629 agomelatine Drugs 0.000 description 1
- YJYPHIXNFHFHND-UHFFFAOYSA-N agomelatine Chemical compound C1=CC=C(CCNC(C)=O)C2=CC(OC)=CC=C21 YJYPHIXNFHFHND-UHFFFAOYSA-N 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 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 description 1
- -1 ethyl acetate compound Chemical class 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 208000024714 major depressive disease Diseases 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229960002748 norepinephrine Drugs 0.000 description 1
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001519 thymoleptic effect Effects 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims (10)
Priority Applications (1)
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CN201410287338.XA CN105218482B (zh) | 2014-06-24 | 2014-06-24 | 沃替西汀氢溴酸盐β晶型的制备方法 |
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CN201410287338.XA CN105218482B (zh) | 2014-06-24 | 2014-06-24 | 沃替西汀氢溴酸盐β晶型的制备方法 |
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CN105218482A true CN105218482A (zh) | 2016-01-06 |
CN105218482B CN105218482B (zh) | 2018-04-06 |
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Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101472906A (zh) * | 2006-06-16 | 2009-07-01 | H.隆德贝克有限公司 | 作为用于治疗认知损伤的、具有结合的对血清素再吸收、5-ht3和5-ht1a活性的化合物的1-[2-(2,4-二甲基苯基硫烷基)-苯基]哌嗪 |
CN102317272A (zh) * | 2009-02-17 | 2012-01-11 | H.隆德贝克有限公司 | 1-[2-(2,4-二甲基苯基硫基)苯基]哌嗪的提纯 |
WO2014044721A1 (en) * | 2012-09-19 | 2014-03-27 | Sandoz Ag | Novel crystalline form of vortioxetine hydrobromide |
WO2014090929A1 (en) * | 2012-12-13 | 2014-06-19 | H. Lundbeck A/S | Compositions comprising vortioxetine and donepezil |
-
2014
- 2014-06-24 CN CN201410287338.XA patent/CN105218482B/zh active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101472906A (zh) * | 2006-06-16 | 2009-07-01 | H.隆德贝克有限公司 | 作为用于治疗认知损伤的、具有结合的对血清素再吸收、5-ht3和5-ht1a活性的化合物的1-[2-(2,4-二甲基苯基硫烷基)-苯基]哌嗪 |
CN102317272A (zh) * | 2009-02-17 | 2012-01-11 | H.隆德贝克有限公司 | 1-[2-(2,4-二甲基苯基硫基)苯基]哌嗪的提纯 |
WO2014044721A1 (en) * | 2012-09-19 | 2014-03-27 | Sandoz Ag | Novel crystalline form of vortioxetine hydrobromide |
WO2014090929A1 (en) * | 2012-12-13 | 2014-06-19 | H. Lundbeck A/S | Compositions comprising vortioxetine and donepezil |
Non-Patent Citations (1)
Title |
---|
王芳 等: "氢溴酸沃替西汀的合成", 《中国医药工业杂志》 * |
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CN105218482B (zh) | 2018-04-06 |
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Address after: Room 4, building 101, No. 1, No. 310018, Hangzhou economic and Technological Development Zone, Zhejiang, China Applicant after: HANGZHOU HEZE PHARMACEUTICAL TECHNOLOGY Co.,Ltd. Address before: Hangzhou City, Zhejiang province 310018 economic and Technological Development Zone No. 6, No. 452 high street Incubator Building 1 room 1B08 Applicant before: HANGZHOU HEZE PHARMACEUTICAL TECHNOLOGY Co.,Ltd. |
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Effective date of registration: 20190506 Address after: 310018 Room 201, Building 101, No. 1 Street, Hangzhou Economic and Technological Development Zone, Hangzhou City, Zhejiang Province Co-patentee after: Hangzhou Heze Xindao Medical Technology Co.,Ltd. Patentee after: HANGZHOU HEZE PHARMACEUTICAL TECHNOLOGY Co.,Ltd. Address before: 310018 Room 201, 4, 1 Avenue 101, Hangzhou economic and Technological Development Zone, Zhejiang. Patentee before: HANGZHOU HEZE PHARMACEUTICAL TECHNOLOGY Co.,Ltd. |
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CP01 | Change in the name or title of a patent holder | ||
CP01 | Change in the name or title of a patent holder |
Address after: 310018 Room 201, Building 101, No. 1 Street, Hangzhou Economic and Technological Development Zone, Hangzhou City, Zhejiang Province Patentee after: Zhejiang Heze Pharmaceutical Technology Co.,Ltd. Patentee after: Hangzhou Heze Xindao Medical Technology Co.,Ltd. Address before: 310018 Room 201, Building 101, No. 1 Street, Hangzhou Economic and Technological Development Zone, Hangzhou City, Zhejiang Province Patentee before: HANGZHOU HEZE PHARMACEUTICAL TECHNOLOGY Co.,Ltd. Patentee before: Hangzhou Heze Xindao Medical Technology Co.,Ltd. |
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CP02 | Change in the address of a patent holder | ||
CP02 | Change in the address of a patent holder |
Address after: Room 201, building 4, No. 101, No. 1 Street, Qiantang New District, Hangzhou City, Zhejiang Province Patentee after: Zhejiang Heze Pharmaceutical Technology Co.,Ltd. Patentee after: Hangzhou Heze Xindao Medical Technology Co.,Ltd. Address before: 310018 Room 201, Building 101, No. 1 Street, Hangzhou Economic and Technological Development Zone, Hangzhou City, Zhejiang Province Patentee before: Zhejiang Heze Pharmaceutical Technology Co.,Ltd. Patentee before: Hangzhou Heze Xindao Medical Technology Co.,Ltd. |
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PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Voltoxetine hydrobromide b Preparation method of crystal form Effective date of registration: 20231202 Granted publication date: 20180406 Pledgee: Agricultural Bank of China Limited Hangzhou Qiantang Branch Pledgor: Zhejiang Heze Pharmaceutical Technology Co.,Ltd. Registration number: Y2023330002921 |