CN109627174A - 一种手性盐酸舍曲林的制备方法 - Google Patents
一种手性盐酸舍曲林的制备方法 Download PDFInfo
- Publication number
- CN109627174A CN109627174A CN201811477972.4A CN201811477972A CN109627174A CN 109627174 A CN109627174 A CN 109627174A CN 201811477972 A CN201811477972 A CN 201811477972A CN 109627174 A CN109627174 A CN 109627174A
- Authority
- CN
- China
- Prior art keywords
- sertraline
- preparation
- organic solvent
- mixed
- solvent
- 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
- 229960003660 sertraline hydrochloride Drugs 0.000 title claims abstract description 67
- 238000002360 preparation method Methods 0.000 title claims abstract description 34
- GLQPTZAAUROJMO-UHFFFAOYSA-N 4-(3,4-dimethoxyphenyl)benzaldehyde Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC=C(C=O)C=C1 GLQPTZAAUROJMO-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 229960002073 sertraline Drugs 0.000 claims abstract description 49
- 238000000034 method Methods 0.000 claims abstract description 33
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 claims abstract description 31
- 239000000706 filtrate Substances 0.000 claims abstract description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 29
- 239000003960 organic solvent Substances 0.000 claims abstract description 27
- 239000007788 liquid Substances 0.000 claims abstract description 26
- 239000002904 solvent Substances 0.000 claims abstract description 25
- IWYDHOAUDWTVEP-SSDOTTSWSA-N (R)-mandelic acid Chemical compound OC(=O)[C@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-SSDOTTSWSA-N 0.000 claims abstract description 24
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 23
- -1 alkali metal salt Chemical class 0.000 claims abstract description 23
- 238000002425 crystallisation Methods 0.000 claims abstract description 23
- 230000008025 crystallization Effects 0.000 claims abstract description 23
- 150000007529 inorganic bases Chemical class 0.000 claims abstract description 22
- 238000000926 separation method Methods 0.000 claims abstract description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000003513 alkali Substances 0.000 claims abstract description 15
- 238000000746 purification Methods 0.000 claims abstract description 15
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- 239000012043 crude product Substances 0.000 claims abstract description 9
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims abstract description 9
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 claims abstract description 6
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 claims abstract description 4
- 229960002510 mandelic acid Drugs 0.000 claims abstract description 4
- 239000012046 mixed solvent Substances 0.000 claims abstract description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 52
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 34
- 239000002585 base Substances 0.000 claims description 20
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 20
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Natural products CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
- 239000012065 filter cake Substances 0.000 claims description 18
- 235000019441 ethanol Nutrition 0.000 claims description 17
- 238000001816 cooling Methods 0.000 claims description 13
- 238000002156 mixing Methods 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 10
- FWDLHTBMGQEUDU-OGFXRTJISA-M sodium;(2r)-2-hydroxy-2-phenylacetate Chemical compound [Na+].[O-]C(=O)[C@H](O)C1=CC=CC=C1 FWDLHTBMGQEUDU-OGFXRTJISA-M 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 150000001298 alcohols Chemical class 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 5
- 238000001953 recrystallisation Methods 0.000 claims description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 5
- 125000005909 ethyl alcohol group Chemical group 0.000 claims description 3
- 239000013078 crystal Substances 0.000 claims description 2
- 239000002244 precipitate Substances 0.000 claims description 2
- 230000000630 rising effect Effects 0.000 claims description 2
- 238000011084 recovery Methods 0.000 abstract description 16
- VGKDLMBJGBXTGI-SJCJKPOMSA-N sertraline Chemical compound C1([C@@H]2CC[C@@H](C3=CC=CC=C32)NC)=CC=C(Cl)C(Cl)=C1 VGKDLMBJGBXTGI-SJCJKPOMSA-N 0.000 abstract description 13
- 239000003795 chemical substances by application Substances 0.000 abstract description 7
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 230000007613 environmental effect Effects 0.000 abstract description 3
- 239000000047 product Substances 0.000 description 18
- 238000004064 recycling Methods 0.000 description 14
- 238000001914 filtration Methods 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 235000011437 Amygdalus communis Nutrition 0.000 description 5
- 241000220304 Prunus dulcis Species 0.000 description 5
- 235000020224 almond Nutrition 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 230000006340 racemization Effects 0.000 description 5
- 238000004821 distillation Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 3
- 238000010981 drying operation Methods 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- FWDLHTBMGQEUDU-UHFFFAOYSA-M sodium;2-hydroxy-2-phenylacetate Chemical compound [Na+].[O-]C(=O)C(O)C1=CC=CC=C1 FWDLHTBMGQEUDU-UHFFFAOYSA-M 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- CMQCNTNASCDNGR-UHFFFAOYSA-N toluene;hydrate Chemical compound O.CC1=CC=CC=C1 CMQCNTNASCDNGR-UHFFFAOYSA-N 0.000 description 3
- 238000010792 warming Methods 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 229940124834 selective serotonin reuptake inhibitor Drugs 0.000 description 2
- 239000012896 selective serotonin reuptake inhibitor Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 244000144730 Amygdalus persica Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010054949 Metaplasia Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 235000006041 Prunus persica f compressa Nutrition 0.000 description 1
- 240000006522 Prunus persica f. compressa Species 0.000 description 1
- 235000006040 Prunus persica var persica Nutrition 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- YDVNLQGCLLPHAH-UHFFFAOYSA-N dichloromethane;hydrate Chemical compound O.ClCCl YDVNLQGCLLPHAH-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- MHYCRLGKOZWVEF-UHFFFAOYSA-N ethyl acetate;hydrate Chemical compound O.CCOC(C)=O MHYCRLGKOZWVEF-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- JEGUKCSWCFPDGT-UHFFFAOYSA-N h2o hydrate Chemical compound O.O JEGUKCSWCFPDGT-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 230000015689 metaplastic ossification Effects 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C211/39—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton
- C07C211/41—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton containing condensed ring systems
- C07C211/42—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton containing condensed ring systems with six-membered aromatic rings being part of the condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
-
- 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
- C07B2200/07—Optical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201811477972.4A CN109627174B (zh) | 2018-12-05 | 2018-12-05 | 一种手性盐酸舍曲林的制备方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201811477972.4A CN109627174B (zh) | 2018-12-05 | 2018-12-05 | 一种手性盐酸舍曲林的制备方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN109627174A true CN109627174A (zh) | 2019-04-16 |
CN109627174B CN109627174B (zh) | 2021-11-12 |
Family
ID=66071219
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201811477972.4A Active CN109627174B (zh) | 2018-12-05 | 2018-12-05 | 一种手性盐酸舍曲林的制备方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN109627174B (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111763150A (zh) * | 2019-12-27 | 2020-10-13 | 上虞京新药业有限公司 | 一种手性盐酸舍曲林的制备方法 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2000297066A (ja) * | 1999-04-12 | 2000-10-24 | Yamakawa Yakuhin Kogyo Kk | 光学活性α−メチルベンジルアミンの製造方法 |
CN103450008A (zh) * | 2013-09-02 | 2013-12-18 | 江苏宝众宝达药业有限公司 | 一种从废水中回收扁桃酸的方法 |
CN103524354A (zh) * | 2013-10-23 | 2014-01-22 | 山东鲁药制药有限公司 | 一种盐酸舍曲林的制备方法 |
CN103570555A (zh) * | 2013-10-14 | 2014-02-12 | 浙江工业大学 | 一种手性盐酸舍曲林的制备方法 |
-
2018
- 2018-12-05 CN CN201811477972.4A patent/CN109627174B/zh active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2000297066A (ja) * | 1999-04-12 | 2000-10-24 | Yamakawa Yakuhin Kogyo Kk | 光学活性α−メチルベンジルアミンの製造方法 |
CN103450008A (zh) * | 2013-09-02 | 2013-12-18 | 江苏宝众宝达药业有限公司 | 一种从废水中回收扁桃酸的方法 |
CN103570555A (zh) * | 2013-10-14 | 2014-02-12 | 浙江工业大学 | 一种手性盐酸舍曲林的制备方法 |
CN103524354A (zh) * | 2013-10-23 | 2014-01-22 | 山东鲁药制药有限公司 | 一种盐酸舍曲林的制备方法 |
Non-Patent Citations (1)
Title |
---|
GENEVIEVE ANKER等: "Resolution of methyl 2-amino-2,4-dideoxy-β-D- and -L-threo-pentopyranoside. Determination of their absolute configuration", 《CARBOHYDRATE RESEARCH》 * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111763150A (zh) * | 2019-12-27 | 2020-10-13 | 上虞京新药业有限公司 | 一种手性盐酸舍曲林的制备方法 |
CN111763150B (zh) * | 2019-12-27 | 2024-03-08 | 上虞京新药业有限公司 | 一种手性盐酸舍曲林的制备方法 |
Also Published As
Publication number | Publication date |
---|---|
CN109627174B (zh) | 2021-11-12 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JPH0377199B2 (zh) | ||
CN105859686B (zh) | 一种达比加群酯游离碱的精制方法 | |
CN109627174A (zh) | 一种手性盐酸舍曲林的制备方法 | |
EP1819661B1 (en) | Crystallization method for benzphetamine | |
JP2012025705A (ja) | (s)−4−〔(4−クロロフェニル)(2−ピリジル)メトキシ〕ピペリジンのジアステレオマー塩の製造方法 | |
JP3110459B2 (ja) | p−アミノフェノール組成物の精製及びN−アセチル−p−アミノフェノールへの直接転化 | |
JPS62158233A (ja) | ビスフエノ−ルAのo,p’−異性体の分離方法 | |
US2178210A (en) | Isolation of leucine and tyrosine from corn gluten | |
JP5092289B2 (ja) | 光学活性N−tert−ブチルカルバモイル−L−tert−ロイシンの製造方法 | |
US8148527B1 (en) | Resolution of 1-(4-methoxybenzyl)-octahydro-isoquinoline | |
JP3484510B2 (ja) | 光学活性カルボン酸の製造法 | |
CN114933588A (zh) | 雷贝拉唑钠粗品的精制方法 | |
CN110872274B (zh) | 分步析晶提纯高残渣盐酸氨丙啉的方法 | |
US7067700B2 (en) | Process for preparing sertraline hydrochloride polymorphic form II | |
CN106749437A (zh) | 一种硫酸氨基葡萄糖氯化钠复盐母液的回收方法 | |
CN110981855B (zh) | 高残渣盐酸氨丙啉的提纯方法 | |
CN101565380A (zh) | L(+)-对氟苯甘氨酸的制备方法 | |
CN111763150B (zh) | 一种手性盐酸舍曲林的制备方法 | |
JP3157724B2 (ja) | インドールの精製方法 | |
CN109369507A (zh) | 一种n-(2,2-二乙氧基乙基)邻苯二甲酰亚胺的提纯方法 | |
CN110402245A (zh) | 外消旋3-烷基哌啶-羧酸乙酯的旋光异构体的分离方法 | |
CN113956183A (zh) | 一种Boc-Ser(Bzl)-OH及其制备方法 | |
SU1334651A1 (ru) | Способ выделени хлоргидрата D, L-трео-1-п-нитрофенил-2-аминопропандиола-1,3 | |
JPH072677B2 (ja) | (±)―2―ヒドロキシ―4―フェニルブタン酸の光学分割法 | |
JPS61161257A (ja) | インドールの濃縮方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant | ||
CP03 | Change of name, title or address | ||
CP03 | Change of name, title or address |
Address after: 312369 No.31, Weisan Road, Shangyu economic and Technological Development Zone, Hangzhou Bay, Shaoxing City, Zhejiang Province Patentee after: Shaoxing Jingxin Pharmaceutical Co.,Ltd. Country or region after: China Patentee after: SHANGHAI JINGXIN BIOLOGICAL MEDICAL Co.,Ltd. Address before: 312500 No. 31, Weisan Road, Shangyu economic and Technological Development Zone, Hangzhou Bay, Shaoxing City, Zhejiang Province Patentee before: SHANGYU JINGXIN PHARMACEUTICAL Co.,Ltd. Country or region before: China Patentee before: SHANGHAI JINGXIN BIOLOGICAL MEDICAL Co.,Ltd. |