UA75147C2 - A process for the preparation of racemic citalopram and/or s-or r- citalopram by separation of the mixture of s- and r- citalopram - Google Patents

A process for the preparation of racemic citalopram and/or s-or r- citalopram by separation of the mixture of s- and r- citalopram Download PDF

Info

Publication number: UA75147C2
Authority: UA; Ukraine
Prior art keywords: citalopram; mixture; acid; racemic; precipitate
Prior art date: 2001-06-25

Application number

UA20031211986A

Other languages

English (en)

Ukrainian (uk)

Inventor

Rikke Eva Humble

Troels Volsgor Christensen

Michael Harold Roc

Original Assignee

Lundbeck & Co As H

Priority date (The priority date 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 date listed.)

2001-06-25

Filing date

2002-06-25

Publication date

2006-03-15

2002-06-25 Application filed by Lundbeck & Co As H filed Critical Lundbeck & Co As H

2006-03-15 Publication of UA75147C2 publication Critical patent/UA75147C2/uk

Links

229960001653 citalopram Drugs 0.000 title abstract description 180
239000000203 mixture Substances 0.000 title abstract description 94
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 abstract description 92
238000000034 method Methods 0.000 title abstract description 37
238000002360 preparation method Methods 0.000 title abstract description 10
238000000926 separation method Methods 0.000 title abstract description 5
239000002253 acid Substances 0.000 abstract description 51
150000003839 salts Chemical class 0.000 abstract description 32
239000002244 precipitate Substances 0.000 abstract description 23
239000002904 solvent Substances 0.000 abstract description 20
239000012458 free base Substances 0.000 abstract description 16
239000012452 mother liquor Substances 0.000 abstract description 16
238000000746 purification Methods 0.000 abstract description 5
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 76
239000003921 oil Substances 0.000 description 33
238000001556 precipitation Methods 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 21
239000000243 solution Substances 0.000 description 21
-1 1-hydroxybutyl Chemical group 0.000 description 19
239000012071 phase Substances 0.000 description 19
238000006243 chemical reaction Methods 0.000 description 18
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
239000013078 crystal Substances 0.000 description 16
238000001704 evaporation Methods 0.000 description 13
239000000126 substance Substances 0.000 description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
230000008020 evaporation Effects 0.000 description 12
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
239000000047 product Substances 0.000 description 10
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 9
230000002378 acidificating effect Effects 0.000 description 9
238000004128 high performance liquid chromatography Methods 0.000 description 9
238000006798 ring closing metathesis reaction Methods 0.000 description 9
239000007787 solid Substances 0.000 description 9
239000010413 mother solution Substances 0.000 description 8
PCOFIIVWHXIDGT-UHFFFAOYSA-N 3-(hydroxymethyl)benzonitrile Chemical compound OCC1=CC=CC(C#N)=C1 PCOFIIVWHXIDGT-UHFFFAOYSA-N 0.000 description 7
150000007513 acids Chemical class 0.000 description 7
239000000654 additive Substances 0.000 description 7
239000002585 base Substances 0.000 description 7
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
230000000996 additive effect Effects 0.000 description 5
229910021529 ammonia Inorganic materials 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
238000004296 chiral HPLC Methods 0.000 description 5
150000001875 compounds Chemical class 0.000 description 5
238000002425 crystallisation Methods 0.000 description 5
230000008025 crystallization Effects 0.000 description 5
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 5
150000003891 oxalate salts Chemical class 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
NWRXEGKWQXAEHC-UHFFFAOYSA-N 2-(hydroxymethyl)benzonitrile Chemical compound OCC1=CC=CC=C1C#N NWRXEGKWQXAEHC-UHFFFAOYSA-N 0.000 description 4
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 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
238000001914 filtration Methods 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
125000004185 ester group Chemical group 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
238000000605 extraction Methods 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
239000011707 mineral Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
238000005191 phase separation Methods 0.000 description 3
238000001953 recrystallisation Methods 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
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
150000001335 aliphatic alkanes Chemical class 0.000 description 2
235000011114 ammonium hydroxide Nutrition 0.000 description 2
239000000935 antidepressant agent Substances 0.000 description 2
229940005513 antidepressants Drugs 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000004140 cleaning Methods 0.000 description 2
230000000875 corresponding effect Effects 0.000 description 2
238000007333 cyanation reaction Methods 0.000 description 2
238000010908 decantation Methods 0.000 description 2
238000001035 drying Methods 0.000 description 2
229960004341 escitalopram Drugs 0.000 description 2
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 2
239000000284 extract Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000007429 general method Methods 0.000 description 2
229910000042 hydrogen bromide Inorganic materials 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
239000013049 sediment Substances 0.000 description 2
229950007352 talopram Drugs 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
PVFOHMXILQEIHX-UHFFFAOYSA-N 8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-9-[2-(2-bromophenyl)ethyl]purin-6-amine Chemical compound C=1C=2OCOC=2C=C(Br)C=1SC1=NC=2C(N)=NC=NC=2N1CCC1=CC=CC=C1Br PVFOHMXILQEIHX-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
FVIGODVHAVLZOO-UHFFFAOYSA-N Dixanthogen Chemical compound CCOC(=S)SSC(=S)OCC FVIGODVHAVLZOO-UHFFFAOYSA-N 0.000 description 1
241000755093 Gaidropsarus vulgaris Species 0.000 description 1
206010028980 Neoplasm Diseases 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
240000003718 Petiveria alliacea Species 0.000 description 1
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
LMDSAFNXCHPEQY-UHFFFAOYSA-N acetonitrile hexane Chemical compound CCCCCC.C(C)#N.C(C)#N LMDSAFNXCHPEQY-UHFFFAOYSA-N 0.000 description 1
PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
230000001430 anti-depressive effect Effects 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
238000005452 bending Methods 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
238000012824 chemical production Methods 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000002596 correlated effect Effects 0.000 description 1
230000008021 deposition Effects 0.000 description 1
238000005137 deposition process Methods 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000000686 essence Substances 0.000 description 1
125000001207 fluorophenyl group Chemical group 0.000 description 1
239000007789 gas Substances 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000010899 nucleation Methods 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
PFPYHYZFFJJQFD-UHFFFAOYSA-N oxalic anhydride Chemical compound O=C1OC1=O PFPYHYZFFJJQFD-UHFFFAOYSA-N 0.000 description 1
230000021962 pH elevation Effects 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
238000012545 processing Methods 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
238000007142 ring opening reaction Methods 0.000 description 1
238000005185 salting out Methods 0.000 description 1
229940124834 selective serotonin reuptake inhibitor Drugs 0.000 description 1
239000012896 selective serotonin reuptake inhibitor Substances 0.000 description 1
239000003772 serotonin uptake inhibitor Substances 0.000 description 1
230000035939 shock Effects 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
239000006104 solid solution Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
LJBBMCNHIUJBDU-UHFFFAOYSA-N talopram Chemical compound O1C(C)(C)C2=CC=CC=C2C1(CCCNC)C1=CC=CC=C1 LJBBMCNHIUJBDU-UHFFFAOYSA-N 0.000 description 1
239000010936 titanium Substances 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
CMQCNTNASCDNGR-UHFFFAOYSA-N toluene;hydrate Chemical compound O.CC1=CC=CC=C1 CMQCNTNASCDNGR-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1

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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Neurology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pain & Pain Management (AREA)
Psychiatry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

UA20031211986A 2001-06-25 2002-06-25 A process for the preparation of racemic citalopram and/or s-or r- citalopram by separation of the mixture of s- and r- citalopram UA75147C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DKPA200100991		2001-06-25
PCT/DK2002/000426 WO2003000672A1 (en)	2001-06-25	2002-06-25	Process for the preparation of racemic citalopram and/or s- or r-citalopram by separation of a mixture of r- and s-citalopram

Publications (1)

Publication Number	Publication Date
UA75147C2 true UA75147C2 (en)	2006-03-15

Family

ID=8160584

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA20031211986A UA75147C2 (en)	2001-06-25	2002-06-25	A process for the preparation of racemic citalopram and/or s-or r- citalopram by separation of the mixture of s- and r- citalopram

Country Status (39)

Country	Link
US (1)	US7112686B2 (cs)
EP (1)	EP1412341B1 (cs)
JP (2)	JP4377219B2 (cs)
KR (4)	KR100939945B1 (cs)
CN (2)	CN101440079B (cs)
AR (2)	AR034612A1 (cs)
AT (1)	ATE284395T1 (cs)
BG (1)	BG66372B1 (cs)
BR (1)	BRPI0210574B8 (cs)
CA (2)	CA2450890C (cs)
CO (1)	CO5550420A2 (cs)
CZ (1)	CZ305034B6 (cs)
DE (1)	DE60202216T2 (cs)
DK (1)	DK1412341T3 (cs)
EA (1)	EA006446B1 (cs)
ES (1)	ES2233834T3 (cs)
HR (1)	HRP20031075B1 (cs)
HU (1)	HU228476B1 (cs)
IL (1)	IL159229A0 (cs)
IS (1)	IS2426B (cs)
JO (1)	JO2389B1 (cs)
MA (1)	MA26260A1 (cs)
ME (2)	ME00027B (cs)
MX (1)	MXPA03011770A (cs)
MY (1)	MY133471A (cs)
NO (2)	NO329873B1 (cs)
NZ (1)	NZ530104A (cs)
PE (1)	PE20030122A1 (cs)
PL (1)	PL366560A1 (cs)
PT (1)	PT1412341E (cs)
RS (1)	RS50673B (cs)
SI (1)	SI1412341T1 (cs)
SK (1)	SK287696B6 (cs)
TN (1)	TNSN02062A1 (cs)
TW (1)	TWI236473B (cs)
UA (1)	UA75147C2 (cs)
UY (2)	UY27356A1 (cs)
WO (1)	WO2003000672A1 (cs)
ZA (1)	ZA200309633B (cs)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AR040970A1 (es)	2002-08-12	2005-04-27	Lundbeck & Co As H	Metodo para la separacion de intermediarios que pueden ser utilizados para la preparacion de escitalopram
NZ540281A (en)	2002-12-23	2008-07-31	Lundbeck & Co As H	Escitalopram hydrobromide and a method for the preparation thereof
SI1581483T1 (sl) *	2002-12-23	2012-09-28	Lundbeck & Co As H	POSTOPEK ZA PRIPRAVO RACEMATNEGA CITALOPRAM DIOLA IN/ALI iS-/i ALI iR-/i CITALOPRAM DIOLOV IN UPORABA TAKIH DIOLOV ZA UÄŚINKOVINO RACEMATNEGA CITALOPRAMA, iR-/i CITALOPRAMA IN/ALI iS-/i CITALOPRAMA
JP4505335B2 (ja)	2002-12-23	2010-07-21	ハー・ルンドベック・アクチエゼルスカベット	ラセミ体シタロプラムジオール（ｒａｃｅｍｉｃｃｉｔａｌｏｐｒａｍｄｉｏｌ）および／またはＳ−もしくはＲ−シタロプラムジオールの製造方法、およびラセミ体シタロプラム、Ｒ−シタロプラムおよび／またはＳ−シタロプラムを製造するために、上記ジオールを使用する方法。
AU2003223105A1 (en) *	2003-03-24	2004-10-18	Hetero Drugs Limited	Novel crystalline forms of (s)-citalopram oxalate
CN100569765C (zh)	2003-12-19	2009-12-16	杭州民生药业集团有限公司	西酞普兰中间体晶体碱
TWI339651B (en) *	2004-02-12	2011-04-01	Lundbeck & Co As H	Method for the separation of intermediates which may be used for the preparation of escitalopram
NZ549100A (en) *	2004-03-05	2010-02-26	Lundbeck & Co As H	Crystalline composition containing escitalopram oxalate
US20050196453A1 (en)	2004-03-05	2005-09-08	H. Lundbeck A/S	Crystalline composition containing escitalopram
ITMI20040717A1 (it)	2004-04-09	2004-07-09	Adorkem Technology Spa	Procedimento chemo-enzimatico per la preparazione dell'escitalopram
JP2006008603A (ja) *	2004-06-25	2006-01-12	Sumitomo Chemical Co Ltd	光学活性シタロプラムの製造方法、その中間体およびその製造方法
KR101166280B1 (ko) *	2004-08-23	2013-11-27	썬 파마 글로벌 에프제트이	시탈로프램 및 에난티오머의 제조 방법
US7989645B2 (en) *	2004-08-23	2011-08-02	Sun Pharma Global Fze	Process for preparation of citalopram and enantiomers
US20110196032A1 (en) *	2005-05-20	2011-08-11	Ashish Gogia	Pharmaceutical Dosage Form of an Antidepressant
US7834201B2 (en)	2005-06-22	2010-11-16	H. Lundbeck A/S	Crystalline base of escitalopram and orodispersible tablets comprising escitalopram base
TWI358407B (en) *	2005-06-22	2012-02-21	Lundbeck & Co As H	Crystalline base of escitalopram and orodispersibl
KR20080080094A (ko)	2005-10-14	2008-09-02	하. 룬트벡 아크티에 셀스카브	에스시탈로프람 및 부프로피온의 저용량 조합물을 이용한중추신경계 장애의 치료 방법
WO2008059514A2 (en) *	2006-07-31	2008-05-22	Cadila Healthcare Limited	Process for preparing escitalopram
US8022232B2 (en)	2007-09-11	2011-09-20	H. Lundbeck A/S	Method for manufacture of escitalopram
FI121570B (fi)	2007-09-11	2011-01-14	Lundbeck & Co As H	Menetelmä essitalopraamin valmistamiseksi
CN100548974C (zh) *	2007-10-11	2009-10-14	浙江大学	西酞普兰中间体的萃取分离方法
CN101560199B (zh) *	2008-04-16	2013-09-18	北京德众万全药物技术开发有限公司	一种依地普仑的制备方法
TWI381813B (zh)	2010-01-12	2013-01-11	Taiwan Paiho Ltd	A Velcro assembly for a foamed article and a foamed article comprising the adhesive tape assembly

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Publication number	Priority date	Publication date	Assignee	Title
GB8419963D0 (en) *	1984-08-06	1984-09-12	Lundbeck & Co As H	Intermediate compound and method
GB8814057D0 (en) *	1988-06-14	1988-07-20	Lundbeck & Co As H	New enantiomers & their isolation
HK1043129B (zh) *	1999-10-25	2004-10-21	H‧隆德贝克有限公司	西酞普蘭的製備方法

2002
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2003
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2004
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Also Published As

Publication number	Publication date
KR20080100498A (ko)	2008-11-18
NO329873B1 (no)	2011-01-17
KR100902530B1 (ko)	2009-06-15
NO335106B1 (no)	2014-09-15
HK1068627A1 (zh)	2005-04-29
ZA200309633B (en)	2005-02-23
EA006446B1 (ru)	2005-12-29
CA2691149A1 (en)	2003-01-03
CN100429208C (zh)	2008-10-29
SK512004A3 (en)	2004-05-04
CN1520405A (zh)	2004-08-11
HU228476B1 (en)	2013-03-28
NO20035671D0 (no)	2003-12-18
BRPI0210574B8 (pt)	2021-05-25
BR0210574A (pt)	2004-08-03
CZ2004131A3 (cs)	2004-04-14
CA2691149C (en)	2011-09-13
NZ530104A (en)	2006-08-31
TNSN02062A1 (en)	2005-12-23
EP1412341A1 (en)	2004-04-28
CA2450890C (en)	2011-02-15
JO2389B1 (en)	2007-06-17
KR100939945B1 (ko)	2010-02-04
SK287696B6 (sk)	2011-06-06
PT1412341E (pt)	2005-04-29
DK1412341T3 (da)	2005-04-04
UY35850A (es)	2016-06-30
MA26260A1 (fr)	2004-09-01
ME00027B (me)	2010-02-10
HUP0400293A2 (hu)	2004-09-28
MY133471A (en)	2007-11-30
RS50673B (sr)	2010-06-30
EP1412341B1 (en)	2004-12-08
JP2009203233A (ja)	2009-09-10
KR20040030702A (ko)	2004-04-09
ATE284395T1 (de)	2004-12-15
IS2426B (is)	2008-10-15
HUP0400293A3 (en)	2007-05-29
AU2002344948B2 (en)	2007-08-16
CO5550420A2 (es)	2005-08-31
AR034612A1 (es)	2004-03-03
RS101403A (sr)	2007-02-05
SI1412341T1 (en)	2005-04-30
MXPA03011770A (es)	2004-04-02
CZ305034B6 (cs)	2015-04-08
JP5064436B2 (ja)	2012-10-31
UY27356A1 (es)	2003-01-31
NO20035671L (no)	2003-12-18
IL159229A0 (en)	2004-06-01
US7112686B2 (en)	2006-09-26
DE60202216D1 (de)	2005-01-13
PE20030122A1 (es)	2003-02-12
CN101440079A (zh)	2009-05-27
CN101440079B (zh)	2011-05-25
JP4377219B2 (ja)	2009-12-02
HK1132729A1 (en)	2010-03-05
HRP20031075B1 (en)	2011-12-31
PL366560A1 (en)	2005-02-07
KR20100052550A (ko)	2010-05-19
TWI236473B (en)	2005-07-21
NO20101420L (no)	2003-12-18
BR0210574B1 (pt)	2014-03-04
HRP20031075A2 (en)	2004-04-30
ES2233834T3 (es)	2005-06-16
KR20090031958A (ko)	2009-03-30
CA2450890A1 (en)	2003-01-03
BG66372B1 (bg)	2013-10-31
WO2003000672A1 (en)	2003-01-03
EA200400082A1 (ru)	2004-06-24
MEP1508A (xx)	2010-02-10
JP2004536093A (ja)	2004-12-02
AR083483A2 (es)	2013-02-27
BG108532A (bg)	2005-04-30
US20040259940A1 (en)	2004-12-23
IS7068A (is)	2003-12-08
DE60202216T2 (de)	2005-12-08

Publication	Publication Date	Title
JP5064436B2 (ja)	2012-10-31	Ｒ−及びｓ−シタロプラムの混合物を分離することによってラセミシタロプラム及びｓ−もしくはｒ−シタロプラムを製造する方法
JP4505335B2 (ja)	2010-07-21	ラセミ体シタロプラムジオール（ｒａｃｅｍｉｃｃｉｔａｌｏｐｒａｍｄｉｏｌ）および／またはＳ−もしくはＲ−シタロプラムジオールの製造方法、およびラセミ体シタロプラム、Ｒ−シタロプラムおよび／またはＳ−シタロプラムを製造するために、上記ジオールを使用する方法。
KR101076640B1 (ko)	2011-10-27	라세미 시탈로프람 디올 및/또는 ｓ― 또는 ｒ―시탈로프람디올의 제조 방법 및 라세미 시탈로프람, ｒ―시탈로프람및/또는 ｓ―시탈로프람의 제조를 위한 상기 디올의 용도
AU2002344948B8 (en)	2007-09-27	Process for the preparation of racemic citalopram and/or S- or R-citalopram by separation of a mixture of R- and S-citalopram
JPH04211079A (ja)	1992-08-03	ｃｉｓ−３−アミノ−４−［２−（２−フリル）エタン−１−イル］−１−メトキシカルボニルメチル−アゼチジン−２−オンの分割方法
HK1068627B (en)	2009-07-17	Process for the preparation of racemic citalopram and/or s-or r-citalopram by separation of a mixture of r- and s-citalopram
HK1132729B (en)	2012-02-24	Process for the preparation of racemic citalopram and/or s- or r-citalopram
AU2002344948A1 (en)	2003-06-19	Process for the preparation of racemic citalopram and/or S- or R-citalopram by separation of a mixture of R- and S-citalopram