NO329873B1 - Fremgangsmate for fremstilling av racemisk citalopram og/eller R- eller S-citalopram ved separasjon av en blanding av R- og S-citalopram med mer enn 50 % av en av enantiomerene - Google Patents

Fremgangsmate for fremstilling av racemisk citalopram og/eller R- eller S-citalopram ved separasjon av en blanding av R- og S-citalopram med mer enn 50 % av en av enantiomerene Download PDF

Info

Publication number: NO329873B1
Authority: NO; Norway
Prior art keywords: citalopram; mixture; mother liquor; acid; addition salt
Prior art date: 2001-06-25

Application number

NO20035671A

Other languages

English (en)

Norwegian (no)

Other versions

NO20035671L (no

NO20035671D0 (no

Inventor

Hans Petersen

Robert Dancer

Ole Nielsen

Michael Harold Rock

Rikke Eva Humble

Troels Volsgaard Christensen

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

2003-12-18

Publication date

2011-01-17

2003-12-18 Application filed by Lundbeck & Co As H filed Critical Lundbeck & Co As H

2003-12-18 Publication of NO20035671L publication Critical patent/NO20035671L/no

2003-12-18 Publication of NO20035671D0 publication Critical patent/NO20035671D0/no

2011-01-17 Publication of NO329873B1 publication Critical patent/NO329873B1/no

Links

229960001653 citalopram Drugs 0.000 title claims description 150
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 description 101
239000000203 mixture Substances 0.000 title claims description 76
238000000034 method Methods 0.000 title claims description 42
238000002360 preparation method Methods 0.000 title claims description 11
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 title claims description 7
239000002253 acid Substances 0.000 claims description 52
239000012452 mother liquor Substances 0.000 claims description 40
150000003839 salts Chemical class 0.000 claims description 34
238000001556 precipitation Methods 0.000 claims description 32
239000002244 precipitate Substances 0.000 claims description 29
239000012458 free base Substances 0.000 claims description 24
239000002904 solvent Substances 0.000 claims description 23
238000006798 ring closing metathesis reaction Methods 0.000 claims description 20
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 14
239000007858 starting material Substances 0.000 claims description 13
238000001704 evaporation Methods 0.000 claims description 11
230000008020 evaporation Effects 0.000 claims description 11
230000002378 acidificating effect Effects 0.000 claims description 9
238000000746 purification Methods 0.000 claims description 8
238000006243 chemical reaction Methods 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 6
238000000926 separation method Methods 0.000 claims description 6
230000015572 biosynthetic process Effects 0.000 claims description 5
150000003891 oxalate salts Chemical class 0.000 claims description 5
125000004185 ester group Chemical group 0.000 claims description 4
238000007363 ring formation reaction Methods 0.000 claims description 4
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims description 4
229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
239000011707 mineral Substances 0.000 claims description 3
238000000605 extraction Methods 0.000 claims description 2
238000002955 isolation Methods 0.000 claims description 2
238000005191 phase separation Methods 0.000 claims description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
239000003921 oil Substances 0.000 description 25
239000013078 crystal Substances 0.000 description 17
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
239000000047 product Substances 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
239000012071 phase Substances 0.000 description 9
239000007787 solid Substances 0.000 description 9
238000004128 high performance liquid chromatography Methods 0.000 description 8
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
238000002425 crystallisation Methods 0.000 description 5
230000008025 crystallization Effects 0.000 description 5
238000010438 heat treatment Methods 0.000 description 5
229960004592 isopropanol Drugs 0.000 description 5
WIHMBLDNRMIGDW-UHFFFAOYSA-N 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-3h-2-benzofuran-5-carbonitrile;hydron;bromide Chemical compound [Br-].O1CC2=CC(C#N)=CC=C2C1(CCC[NH+](C)C)C1=CC=C(F)C=C1 WIHMBLDNRMIGDW-UHFFFAOYSA-N 0.000 description 4
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
238000001914 filtration Methods 0.000 description 4
229910000042 hydrogen bromide Inorganic materials 0.000 description 4
230000014759 maintenance of location Effects 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
239000002585 base Substances 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
238000001035 drying Methods 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
239000000284 extract Substances 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
SYTBZMRGLBWNTM-SNVBAGLBSA-N (R)-flurbiprofen Chemical compound FC1=CC([C@H](C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-SNVBAGLBSA-N 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
239000000935 antidepressant agent Substances 0.000 description 2
229940005513 antidepressants Drugs 0.000 description 2
239000000010 aprotic solvent Substances 0.000 description 2
238000013475 authorization Methods 0.000 description 2
238000004296 chiral HPLC Methods 0.000 description 2
238000013375 chromatographic separation Methods 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
238000007333 cyanation reaction Methods 0.000 description 2
238000010908 decantation 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
150000002148 esters Chemical class 0.000 description 2
238000007689 inspection Methods 0.000 description 2
238000010899 nucleation Methods 0.000 description 2
235000006408 oxalic acid Nutrition 0.000 description 2
239000003586 protic polar solvent 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
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
FIXQPYBPVRAVND-UHFFFAOYSA-N 1-[4-bromo-2-(hydroxymethyl)phenyl]-4-(dimethylamino)-1-(4-fluorophenyl)butan-1-ol Chemical compound C=1C=C(Br)C=C(CO)C=1C(O)(CCCN(C)C)C1=CC=C(F)C=C1 FIXQPYBPVRAVND-UHFFFAOYSA-N 0.000 description 1
RVGFHORHCHHPCZ-UHFFFAOYSA-N 4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)benzonitrile;hydrobromide Chemical compound Br.C=1C=C(C#N)C=C(CO)C=1C(O)(CCCN(C)C)C1=CC=C(F)C=C1 RVGFHORHCHHPCZ-UHFFFAOYSA-N 0.000 description 1
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
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
-1 acetone Chemical compound 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
230000001430 anti-depressive effect Effects 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
150000001491 aromatic compounds Chemical class 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
238000004587 chromatography analysis Methods 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
238000010586 diagram Methods 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000000463 material Substances 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
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
239000003960 organic solvent Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000005185 salting out Methods 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000003786 synthesis reaction Methods 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (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)

NO20035671A 2001-06-25 2003-12-18 Fremgangsmate for fremstilling av racemisk citalopram og/eller R- eller S-citalopram ved separasjon av en blanding av R- og S-citalopram med mer enn 50 % av en av enantiomerene NO329873B1 (no)

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 (3)

Publication Number	Publication Date
NO20035671L NO20035671L (no)	2003-12-18
NO20035671D0 NO20035671D0 (no)	2003-12-18
NO329873B1 true NO329873B1 (no)	2011-01-17

Family

ID=8160584

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
NO20035671A NO329873B1 (no)	2001-06-25	2003-12-18	Fremgangsmate for fremstilling av racemisk citalopram og/eller R- eller S-citalopram ved separasjon av en blanding av R- og S-citalopram med mer enn 50 % av en av enantiomerene
NO20101420A NO335106B1 (no)	2001-06-25	2010-10-13	Fremgangsmåte for fremstilling av en blanding av R- og S-citalopram med mer enn 50 % av S- eller R-enantiomeren

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
NO20101420A NO335106B1 (no)	2001-06-25	2010-10-13	Fremgangsmåte for fremstilling av en blanding av R- og S-citalopram med mer enn 50 % av S- eller R-enantiomeren

Country Status (39)

Country	Link
US (1)	US7112686B2 (de)
EP (1)	EP1412341B1 (de)
JP (2)	JP4377219B2 (de)
KR (4)	KR20080100498A (de)
CN (2)	CN101440079B (de)
AR (2)	AR034612A1 (de)
AT (1)	ATE284395T1 (de)
BG (1)	BG66372B1 (de)
BR (1)	BRPI0210574B8 (de)
CA (2)	CA2691149C (de)
CO (1)	CO5550420A2 (de)
CZ (1)	CZ305034B6 (de)
DE (1)	DE60202216T2 (de)
DK (1)	DK1412341T3 (de)
EA (1)	EA006446B1 (de)
ES (1)	ES2233834T3 (de)
HR (1)	HRP20031075B1 (de)
HU (1)	HU228476B1 (de)
IL (1)	IL159229A0 (de)
IS (1)	IS2426B (de)
JO (1)	JO2389B1 (de)
MA (1)	MA26260A1 (de)
ME (2)	ME00027B (de)
MX (1)	MXPA03011770A (de)
MY (1)	MY133471A (de)
NO (2)	NO329873B1 (de)
NZ (1)	NZ530104A (de)
PE (1)	PE20030122A1 (de)
PL (1)	PL366560A1 (de)
PT (1)	PT1412341E (de)
RS (1)	RS50673B (de)
SI (1)	SI1412341T1 (de)
SK (1)	SK287696B6 (de)
TN (1)	TNSN02062A1 (de)
TW (1)	TWI236473B (de)
UA (1)	UA75147C2 (de)
UY (2)	UY27356A1 (de)
WO (1)	WO2003000672A1 (de)
ZA (1)	ZA200309633B (de)

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
EP2363389A1 (de)	2002-12-23	2011-09-07	H. Lundbeck A/S	Verfahren zur Herstellung von racemischen Citalopram-Diol und/oder S- oder R-citalopram-Diolen und deren Verwendung zur Herstellung von racemischen Citalopram, R-Citalopram und/oder S-Citalopram
EA009061B1 (ru) *	2002-12-23	2007-10-26	Х. Лундбекк А/С	Способ получения рацемического циталопрамдиола и/или s- или r- циталопрамдиолов и способ получения рацемического циталопрама, r-циталопрама и /или s-циталопрама
AU2003287919B2 (en)	2002-12-23	2009-11-12	H. Lundbeck A/S	Escitalopram hydrobromide and a method for the preparation thereof
WO2004085416A1 (en) *	2003-03-24	2004-10-07	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
US20050196453A1 (en)	2004-03-05	2005-09-08	H. Lundbeck A/S	Crystalline composition containing escitalopram
WO2005084643A1 (en) *	2004-03-05	2005-09-15	H. Lundbeck A/S	Crystalline composition containing escitalopram oxalate
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
US7989645B2 (en) *	2004-08-23	2011-08-02	Sun Pharma Global Fze	Process for preparation of citalopram and enantiomers
ES2285972T1 (es)	2004-08-23	2007-12-01	Sun Pharmaceutical Industries Limited	Procedimiento de fabricacion de citalopram y enantiomeros.
WO2006123243A2 (en) *	2005-05-20	2006-11-23	Aurobindo Pharma Limited	Pharmaceutical dosage forms comprising escitalopram in form of granules
TWI347942B (en) *	2005-06-22	2011-09-01	Lundbeck & Co As H	Crystalline base of escitalopram and orodispersible tablets comprising escitalopram base
US7834201B2 (en)	2005-06-22	2010-11-16	H. Lundbeck A/S	Crystalline base of escitalopram and orodispersible tablets comprising escitalopram base
EA200801081A1 (ru)	2005-10-14	2008-10-30	Х. Лундбекк А/С	Способы лечения расстройств центральной нервной системы комбинацией малых доз эсциталопрама и бупропиона
WO2008059514A2 (en) *	2006-07-31	2008-05-22	Cadila Healthcare Limited	Process for preparing escitalopram
FI121570B (fi)	2007-09-11	2011-01-14	Lundbeck & Co As H	Menetelmä essitalopraamin valmistamiseksi
US8022232B2 (en) *	2007-09-11	2011-09-20	H. Lundbeck A/S	Method for manufacture of escitalopram
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

Family Cites Families (3)

* Cited by examiner, † Cited by third party
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
HRP20020344B1 (hr) *	1999-10-25	2010-10-31	H. Lundbeck A/S	Način priprave citaloprama

2002
- 2002-06-21 AR ARP020102350A patent/AR034612A1/es active IP Right Grant
- 2002-06-23 JO JO200265A patent/JO2389B1/en active
- 2002-06-24 PE PE2002000551A patent/PE20030122A1/es active IP Right Grant
- 2002-06-24 TN TNTNSN02062A patent/TNSN02062A1/en unknown
- 2002-06-25 EP EP02742848A patent/EP1412341B1/de not_active Expired - Lifetime
- 2002-06-25 US US10/482,000 patent/US7112686B2/en not_active Expired - Lifetime
- 2002-06-25 HU HU0400293A patent/HU228476B1/hu unknown
- 2002-06-25 MA MA26713A patent/MA26260A1/fr unknown
- 2002-06-25 UA UA20031211986A patent/UA75147C2/uk unknown
- 2002-06-25 RS YUP-1014/03A patent/RS50673B/sr unknown
- 2002-06-25 WO PCT/DK2002/000426 patent/WO2003000672A1/en not_active Ceased
- 2002-06-25 KR KR1020087026708A patent/KR20080100498A/ko not_active Ceased
- 2002-06-25 CZ CZ2004-131A patent/CZ305034B6/cs not_active IP Right Cessation
- 2002-06-25 SI SI200230078T patent/SI1412341T1/xx unknown
- 2002-06-25 BR BRPI0210574A patent/BRPI0210574B8/pt not_active IP Right Cessation
- 2002-06-25 DE DE60202216T patent/DE60202216T2/de not_active Expired - Lifetime
- 2002-06-25 HR HR20031075A patent/HRP20031075B1/xx not_active IP Right Cessation
- 2002-06-25 EA EA200400082A patent/EA006446B1/ru not_active IP Right Cessation
- 2002-06-25 NZ NZ530104A patent/NZ530104A/en not_active IP Right Cessation
- 2002-06-25 JP JP2003507077A patent/JP4377219B2/ja not_active Expired - Lifetime
- 2002-06-25 ME MEP-2008-15A patent/ME00027B/me unknown
- 2002-06-25 CA CA2691149A patent/CA2691149C/en not_active Expired - Fee Related
- 2002-06-25 SK SK51-2004A patent/SK287696B6/sk unknown
- 2002-06-25 CA CA2450890A patent/CA2450890C/en not_active Expired - Fee Related
- 2002-06-25 ME MEP-15/08A patent/MEP1508A/xx unknown
- 2002-06-25 UY UY27356A patent/UY27356A1/es not_active IP Right Cessation
- 2002-06-25 KR KR1020037016853A patent/KR100902530B1/ko not_active Expired - Lifetime
- 2002-06-25 AT AT02742848T patent/ATE284395T1/de active
- 2002-06-25 DK DK02742848T patent/DK1412341T3/da active
- 2002-06-25 IL IL15922902A patent/IL159229A0/xx active IP Right Grant
- 2002-06-25 PT PT02742848T patent/PT1412341E/pt unknown
- 2002-06-25 MY MYPI20022382A patent/MY133471A/en unknown
- 2002-06-25 CN CN2008102158851A patent/CN101440079B/zh not_active Expired - Lifetime
- 2002-06-25 ES ES02742848T patent/ES2233834T3/es not_active Expired - Lifetime
- 2002-06-25 TW TW091113845A patent/TWI236473B/zh not_active IP Right Cessation
- 2002-06-25 PL PL02366560A patent/PL366560A1/xx not_active Application Discontinuation
- 2002-06-25 CN CNB028126688A patent/CN100429208C/zh not_active Expired - Lifetime
- 2002-06-25 KR KR1020107006751A patent/KR20100052550A/ko not_active Ceased
- 2002-06-25 KR KR1020097004586A patent/KR100939945B1/ko not_active Expired - Lifetime
- 2002-06-25 MX MXPA03011770A patent/MXPA03011770A/es active IP Right Grant
2003
- 2003-12-08 IS IS7068A patent/IS2426B/is unknown
- 2003-12-11 ZA ZA2003/09633A patent/ZA200309633B/en unknown
- 2003-12-18 NO NO20035671A patent/NO329873B1/no not_active IP Right Cessation
2004
- 2004-01-14 BG BG108532A patent/BG66372B1/bg unknown
- 2004-01-22 CO CO04004620A patent/CO5550420A2/es not_active Application Discontinuation
2009
- 2009-04-17 JP JP2009101188A patent/JP5064436B2/ja not_active Expired - Lifetime
2010
- 2010-10-13 NO NO20101420A patent/NO335106B1/no not_active IP Right Cessation
2011
- 2011-10-19 AR ARP110103869A patent/AR083483A2/es active IP Right Grant
2014
- 2014-11-21 UY UY0001035850A patent/UY35850A/es not_active IP Right Cessation

Also Published As

Publication number	Publication date
HRP20031075A2 (en)	2004-04-30
BG108532A (bg)	2005-04-30
UY27356A1 (es)	2003-01-31
NO20035671L (no)	2003-12-18
JP4377219B2 (ja)	2009-12-02
JP2004536093A (ja)	2004-12-02
NZ530104A (en)	2006-08-31
NO335106B1 (no)	2014-09-15
EA200400082A1 (ru)	2004-06-24
KR20090031958A (ko)	2009-03-30
DE60202216D1 (de)	2005-01-13
BR0210574B1 (pt)	2014-03-04
EA006446B1 (ru)	2005-12-29
MA26260A1 (fr)	2004-09-01
CZ2004131A3 (cs)	2004-04-14
KR100902530B1 (ko)	2009-06-15
TWI236473B (en)	2005-07-21
HK1132729A1 (en)	2010-03-05
MEP1508A (xx)	2010-02-10
SK512004A3 (en)	2004-05-04
IS2426B (is)	2008-10-15
CN101440079B (zh)	2011-05-25
NO20035671D0 (no)	2003-12-18
CA2691149C (en)	2011-09-13
AR034612A1 (es)	2004-03-03
TNSN02062A1 (en)	2005-12-23
AU2002344948B2 (en)	2007-08-16
JO2389B1 (en)	2007-06-17
HK1068627A1 (zh)	2005-04-29
BR0210574A (pt)	2004-08-03
WO2003000672A1 (en)	2003-01-03
RS50673B (sr)	2010-06-30
KR20080100498A (ko)	2008-11-18
RS101403A (sr)	2007-02-05
DE60202216T2 (de)	2005-12-08
NO20101420L (no)	2003-12-18
ZA200309633B (en)	2005-02-23
CN1520405A (zh)	2004-08-11
KR20040030702A (ko)	2004-04-09
PT1412341E (pt)	2005-04-29
AR083483A2 (es)	2013-02-27
DK1412341T3 (da)	2005-04-04
CA2450890A1 (en)	2003-01-03
JP2009203233A (ja)	2009-09-10
US7112686B2 (en)	2006-09-26
CA2450890C (en)	2011-02-15
JP5064436B2 (ja)	2012-10-31
BRPI0210574B8 (pt)	2021-05-25
IS7068A (is)	2003-12-08
ME00027B (me)	2010-02-10
EP1412341A1 (de)	2004-04-28
CO5550420A2 (es)	2005-08-31
UY35850A (es)	2016-06-30
HUP0400293A2 (hu)	2004-09-28
HU228476B1 (en)	2013-03-28
US20040259940A1 (en)	2004-12-23
UA75147C2 (en)	2006-03-15
CN101440079A (zh)	2009-05-27
PL366560A1 (en)	2005-02-07
SK287696B6 (sk)	2011-06-06
MY133471A (en)	2007-11-30
BG66372B1 (bg)	2013-10-31
ES2233834T3 (es)	2005-06-16
KR20100052550A (ko)	2010-05-19
SI1412341T1 (en)	2005-04-30
CA2691149A1 (en)	2003-01-03
CN100429208C (zh)	2008-10-29
HUP0400293A3 (en)	2007-05-29
IL159229A0 (en)	2004-06-01
KR100939945B1 (ko)	2010-02-04
MXPA03011770A (es)	2004-04-02
CZ305034B6 (cs)	2015-04-08
ATE284395T1 (de)	2004-12-15
PE20030122A1 (es)	2003-02-12
EP1412341B1 (de)	2004-12-08
HRP20031075B1 (en)	2011-12-31

Legal Events

Date	Code	Title	Description
2008-07-14	CREP	Change of representative	Representative=s name: PLOUGMANN & VINGTOFT, POSTBOKS 1003 SENTRUM, 0104
2022-07-11	MK1K	Patent expired

Publication	Publication Date	Title
NO335106B1 (no)	2014-09-15	Fremgangsmåte for fremstilling av en blanding av R- og S-citalopram med mer enn 50 % av S- eller R-enantiomeren
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。
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
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
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
HK1132729B (en)	2012-02-24	Process for the preparation of racemic citalopram and/or s- or r-citalopram
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