CN100334071C - 外消旋西酞普兰二醇和 /或 s －或 r－西酞普兰二醇的制备方法及这些二醇在制备外消旋西酞普兰二醇、 r －西酞普兰和 /或 s －西酞普兰中的用途 - Google Patents
外消旋西酞普兰二醇和 /或 s －或 r－西酞普兰二醇的制备方法及这些二醇在制备外消旋西酞普兰二醇、 r －西酞普兰和 /或 s －西酞普兰中的用途 Download PDFInfo
- Publication number
- CN100334071C CN100334071C CNB200380107283XA CN200380107283A CN100334071C CN 100334071 C CN100334071 C CN 100334071C CN B200380107283X A CNB200380107283X A CN B200380107283XA CN 200380107283 A CN200380107283 A CN 200380107283A CN 100334071 C CN100334071 C CN 100334071C
- Authority
- CN
- China
- Prior art keywords
- glycol
- citalopram
- acid salt
- free alkali
- 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.)
- Expired - Lifetime
Links
- 229960001653 citalopram Drugs 0.000 title claims abstract description 144
- WSEQXVZVJXJVFP-HXUWFJFHSA-N (R)-citalopram Chemical compound C1([C@@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WSEQXVZVJXJVFP-HXUWFJFHSA-N 0.000 title claims abstract description 76
- 238000000034 method Methods 0.000 title claims abstract description 69
- 238000002360 preparation method Methods 0.000 title claims abstract description 23
- -1 citalopram diol Chemical class 0.000 title abstract description 11
- 150000002009 diols Chemical class 0.000 title description 34
- 239000002253 acid Substances 0.000 claims abstract description 243
- 150000003839 salts Chemical class 0.000 claims abstract description 222
- 239000000203 mixture Substances 0.000 claims abstract description 144
- 239000002904 solvent Substances 0.000 claims abstract description 69
- 238000000926 separation method Methods 0.000 claims abstract description 21
- 238000001953 recrystallisation Methods 0.000 claims abstract description 19
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 254
- 239000003513 alkali Substances 0.000 claims description 199
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 127
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 81
- 238000001556 precipitation Methods 0.000 claims description 63
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 56
- 239000013078 crystal Substances 0.000 claims description 37
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 24
- 239000012452 mother liquor Substances 0.000 claims description 23
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 238000001704 evaporation Methods 0.000 claims description 12
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 7
- 238000004090 dissolution Methods 0.000 claims description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 6
- 235000006408 oxalic acid Nutrition 0.000 claims description 6
- 150000002576 ketones Chemical class 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 150000003016 phosphoric acids Chemical class 0.000 claims description 2
- 239000002798 polar solvent Substances 0.000 claims description 2
- 238000000638 solvent extraction Methods 0.000 claims 1
- 235000012976 tarts Nutrition 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 239000002244 precipitate Substances 0.000 abstract description 7
- 238000000746 purification Methods 0.000 abstract description 6
- 239000012458 free base Substances 0.000 abstract 3
- GNULRNVWXYXBQY-UHFFFAOYSA-N 4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)benzonitrile Chemical compound C=1C=C(C#N)C=C(CO)C=1C(O)(CCCN(C)C)C1=CC=C(F)C=C1 GNULRNVWXYXBQY-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- 238000006798 ring closing metathesis reaction Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 33
- 239000007787 solid Substances 0.000 description 27
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 26
- 239000000047 product Substances 0.000 description 17
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 16
- 239000011780 sodium chloride Substances 0.000 description 13
- 239000007788 liquid Substances 0.000 description 12
- 238000007363 ring formation reaction Methods 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 11
- 239000012071 phase Substances 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 229910021529 ammonia Inorganic materials 0.000 description 8
- 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 8
- 229960004341 escitalopram Drugs 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- 238000007429 general method Methods 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 238000011084 recovery Methods 0.000 description 8
- 238000009834 vaporization Methods 0.000 description 8
- 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 7
- 238000000247 postprecipitation Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 6
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 6
- 238000010908 decantation Methods 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- PCOFIIVWHXIDGT-UHFFFAOYSA-N 3-(hydroxymethyl)benzonitrile Chemical compound OCC1=CC=CC(C#N)=C1 PCOFIIVWHXIDGT-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000935 antidepressant agent Substances 0.000 description 2
- 235000021463 dry cake Nutrition 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 2
- 239000012454 non-polar solvent Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 229940124834 selective serotonin reuptake inhibitor Drugs 0.000 description 2
- 239000012896 selective serotonin reuptake inhibitor Substances 0.000 description 2
- 239000011973 solid acid Substances 0.000 description 2
- 238000004808 supercritical fluid chromatography Methods 0.000 description 2
- 230000001519 thymoleptic effect Effects 0.000 description 2
- GNULRNVWXYXBQY-HXUWFJFHSA-N 4-[(1r)-4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)benzonitrile Chemical compound C1([C@](O)(CCCN(C)C)C=2C(=CC(=CC=2)C#N)CO)=CC=C(F)C=C1 GNULRNVWXYXBQY-HXUWFJFHSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/32—Separation; Purification; Stabilisation; Use of additives
- C07C253/34—Separation; Purification
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/275—Nitriles; Isonitriles
- A61K31/277—Nitriles; Isonitriles having a ring, e.g. verapamil
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA200202004 | 2002-12-23 | ||
| DKPA200202004 | 2002-12-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1729164A CN1729164A (zh) | 2006-02-01 |
| CN100334071C true CN100334071C (zh) | 2007-08-29 |
Family
ID=35423357
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB200380107283XA Expired - Lifetime CN100334071C (zh) | 2002-12-23 | 2003-12-18 | 外消旋西酞普兰二醇和 /或 s －或 r－西酞普兰二醇的制备方法及这些二醇在制备外消旋西酞普兰二醇、 r －西酞普兰和 /或 s －西酞普兰中的用途 |
Country Status (17)
| Country | Link |
|---|---|
| KR (1) | KR101076640B1 (sl) |
| CN (1) | CN100334071C (sl) |
| AR (1) | AR042655A1 (sl) |
| BR (1) | BR0317629A (sl) |
| DK (1) | DK1581483T3 (sl) |
| EA (1) | EA009061B1 (sl) |
| ES (1) | ES2385975T3 (sl) |
| ME (1) | MEP5708A (sl) |
| MY (1) | MY142404A (sl) |
| PE (1) | PE20050065A1 (sl) |
| PT (1) | PT1581483E (sl) |
| RS (1) | RS52152B (sl) |
| SI (1) | SI1581483T1 (sl) |
| TW (1) | TWI331605B (sl) |
| UA (1) | UA84859C2 (sl) |
| UY (1) | UY28146A1 (sl) |
| ZA (1) | ZA200504715B (sl) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA95199U (uk) | 2014-07-09 | 2014-12-10 | Дозатор з точним дозуванням для сипучих продуктів | |
| CN110590602B (zh) * | 2019-09-25 | 2022-04-05 | 浙江海森药业股份有限公司 | 外消旋西酞普兰二醇的拆分精制方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0347066A1 (en) * | 1988-06-14 | 1989-12-20 | H. Lundbeck A/S | New enantiomers and their isolation |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR034612A1 (es) * | 2001-06-25 | 2004-03-03 | Lundbeck & Co As H | Proceso para la preparacion del citalopram racemico y/o del s- o r-citalopram mediante la separacion de una mezcla de r- y s-citalopram |
-
2003
- 2003-12-18 SI SI200332174T patent/SI1581483T1/sl unknown
- 2003-12-18 CN CNB200380107283XA patent/CN100334071C/zh not_active Expired - Lifetime
- 2003-12-18 PT PT03767476T patent/PT1581483E/pt unknown
- 2003-12-18 UA UAA200506921A patent/UA84859C2/ru unknown
- 2003-12-18 EA EA200501042A patent/EA009061B1/ru not_active IP Right Cessation
- 2003-12-18 DK DK03767476.9T patent/DK1581483T3/da active
- 2003-12-18 BR BR0317629-0A patent/BR0317629A/pt not_active Application Discontinuation
- 2003-12-18 KR KR1020057011898A patent/KR101076640B1/ko not_active IP Right Cessation
- 2003-12-18 RS YU20050488A patent/RS52152B/sr unknown
- 2003-12-18 ES ES03767476T patent/ES2385975T3/es not_active Expired - Lifetime
- 2003-12-18 ME MEP-57/08A patent/MEP5708A/xx unknown
- 2003-12-18 TW TW092135925A patent/TWI331605B/zh not_active IP Right Cessation
- 2003-12-22 MY MYPI20034948A patent/MY142404A/en unknown
- 2003-12-22 AR ARP030104781A patent/AR042655A1/es unknown
- 2003-12-22 UY UY28146A patent/UY28146A1/es not_active Application Discontinuation
-
2004
- 2004-01-05 PE PE2004000033A patent/PE20050065A1/es not_active Application Discontinuation
-
2005
- 2005-06-09 ZA ZA200504715A patent/ZA200504715B/en unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0347066A1 (en) * | 1988-06-14 | 1989-12-20 | H. Lundbeck A/S | New enantiomers and their isolation |
Also Published As
| Publication number | Publication date |
|---|---|
| BR0317629A (pt) | 2005-11-29 |
| RS52152B (sr) | 2012-08-31 |
| PT1581483E (pt) | 2012-07-24 |
| ME00034B (me) | 2010-02-10 |
| ZA200504715B (en) | 2006-08-30 |
| MEP5708A (xx) | 2010-02-10 |
| UY28146A1 (es) | 2004-07-30 |
| RS20050488A (en) | 2007-06-04 |
| MY142404A (en) | 2010-11-30 |
| UA84859C2 (ru) | 2008-12-10 |
| EA009061B1 (ru) | 2007-10-26 |
| TW200512202A (en) | 2005-04-01 |
| DK1581483T3 (da) | 2012-07-23 |
| PE20050065A1 (es) | 2005-02-18 |
| ES2385975T3 (es) | 2012-08-06 |
| EA200501042A1 (ru) | 2005-12-29 |
| KR101076640B1 (ko) | 2011-10-27 |
| KR20050093801A (ko) | 2005-09-23 |
| CN1729164A (zh) | 2006-02-01 |
| AR042655A1 (es) | 2005-06-29 |
| SI1581483T1 (sl) | 2012-09-28 |
| TWI331605B (en) | 2010-10-11 |
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