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 PDFInfo
- Publication number
- NO329873B1 NO329873B1 NO20035671A NO20035671A NO329873B1 NO 329873 B1 NO329873 B1 NO 329873B1 NO 20035671 A NO20035671 A NO 20035671A NO 20035671 A NO20035671 A NO 20035671A NO 329873 B1 NO329873 B1 NO 329873B1
- Authority
- NO
- Norway
- Prior art keywords
- citalopram
- mixture
- mother liquor
- acid
- addition salt
- Prior art date
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)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (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)
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 |
|---|---|
| NO20035671D0 NO20035671D0 (no) | 2003-12-18 |
| NO20035671L NO20035671L (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 (40)
| Country | Link |
|---|---|
| US (1) | US7112686B2 (pl) |
| EP (1) | EP1412341B1 (pl) |
| JP (2) | JP4377219B2 (pl) |
| KR (4) | KR100902530B1 (pl) |
| CN (2) | CN101440079B (pl) |
| AR (2) | AR034612A1 (pl) |
| AT (1) | ATE284395T1 (pl) |
| BG (1) | BG66372B1 (pl) |
| BR (1) | BRPI0210574B8 (pl) |
| CA (2) | CA2450890C (pl) |
| CO (1) | CO5550420A2 (pl) |
| CZ (1) | CZ305034B6 (pl) |
| DE (1) | DE60202216T2 (pl) |
| DK (1) | DK1412341T3 (pl) |
| EA (1) | EA006446B1 (pl) |
| ES (1) | ES2233834T3 (pl) |
| HK (2) | HK1068627A1 (pl) |
| HR (1) | HRP20031075B1 (pl) |
| HU (1) | HU228476B1 (pl) |
| IL (1) | IL159229A0 (pl) |
| IS (1) | IS2426B (pl) |
| JO (1) | JO2389B1 (pl) |
| MA (1) | MA26260A1 (pl) |
| ME (2) | ME00027B (pl) |
| MX (1) | MXPA03011770A (pl) |
| MY (1) | MY133471A (pl) |
| NO (2) | NO329873B1 (pl) |
| NZ (1) | NZ530104A (pl) |
| PE (1) | PE20030122A1 (pl) |
| PL (1) | PL366560A1 (pl) |
| PT (1) | PT1412341E (pl) |
| RS (1) | RS50673B (pl) |
| SI (1) | SI1412341T1 (pl) |
| SK (1) | SK287696B6 (pl) |
| TN (1) | TNSN02062A1 (pl) |
| TW (1) | TWI236473B (pl) |
| UA (1) | UA75147C2 (pl) |
| UY (2) | UY27356A1 (pl) |
| WO (1) | WO2003000672A1 (pl) |
| ZA (1) | ZA200309633B (pl) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PE20040991A1 (es) | 2002-08-12 | 2004-12-27 | Lundbeck & Co As H | Separacion de intermediarios para la preparacion de escitalopram |
| MEP5708A (xx) * | 2002-12-23 | 2010-02-10 | Lundbeck & Co As H | Postupak pripremanja racemskog citalopram diola i/ili r-citalopram diola i upotreba takvih diola za pripremanje racemskog citaloprama , r-citaloprama i/ili s-citaloprama. |
| EP2363389A1 (en) * | 2002-12-23 | 2011-09-07 | H. Lundbeck A/S | A process for the preparation of racemic citalopram diol and/or S- or R-citalopram diols and the use of such diols for the preparation of racemic citalopram, R-citalopram and/or S-citalopram |
| ATE388947T1 (de) | 2002-12-23 | 2008-03-15 | Lundbeck & Co As H | Escitalopramhydrobromid und ein verfahren zu dessen herstellung |
| TR200504022T1 (tr) * | 2003-03-24 | 2006-08-21 | Hetero Drugs Limited | (S)-sitalopram oksalatın yeni sıvı kristal formları. |
| 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 |
| EP1732514A1 (en) * | 2004-03-05 | 2006-12-20 | H. Lundbeck A/S | 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 |
| US7989645B2 (en) * | 2004-08-23 | 2011-08-02 | Sun Pharma Global Fze | Process for preparation of citalopram and enantiomers |
| EP1797060A2 (en) | 2004-08-23 | 2007-06-20 | Sun Pharmaceutical Industries Limited | "process for preparation of citalopram and enantiomers" |
| 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 |
| JP2009511606A (ja) | 2005-10-14 | 2009-03-19 | ハー・ルンドベック・アクチエゼルスカベット | エスシタロプラムおよびブプロピオンの低用量の併用を用いる中枢神経系障害の治療方法 |
| 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 |
Family Cites Families (3)
| 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 |
| TR200401456T1 (tr) * | 1999-10-25 | 2005-04-21 | H. Lundbeck A/S | Sitalopram hazırlanması için yöntem. |
-
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 UA UA20031211986A patent/UA75147C2/uk unknown
- 2002-06-25 CN CN2008102158851A patent/CN101440079B/zh not_active Expired - Lifetime
- 2002-06-25 CA CA2450890A patent/CA2450890C/en not_active Expired - Fee Related
- 2002-06-25 TW TW091113845A patent/TWI236473B/zh not_active IP Right Cessation
- 2002-06-25 US US10/482,000 patent/US7112686B2/en not_active Expired - Lifetime
- 2002-06-25 IL IL15922902A patent/IL159229A0/xx active IP Right Grant
- 2002-06-25 KR KR1020037016853A patent/KR100902530B1/ko active IP Right Grant
- 2002-06-25 CA CA2691149A patent/CA2691149C/en not_active Expired - Fee Related
- 2002-06-25 ME MEP-2008-15A patent/ME00027B/me unknown
- 2002-06-25 ME MEP-15/08A patent/MEP1508A/xx unknown
- 2002-06-25 SI SI200230078T patent/SI1412341T1/xx unknown
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