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
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 (ja) |
| EP (1) | EP1412341B1 (ja) |
| JP (2) | JP4377219B2 (ja) |
| KR (4) | KR20100052550A (ja) |
| CN (2) | CN100429208C (ja) |
| AR (2) | AR034612A1 (ja) |
| AT (1) | ATE284395T1 (ja) |
| BG (1) | BG66372B1 (ja) |
| BR (1) | BRPI0210574B8 (ja) |
| CA (2) | CA2450890C (ja) |
| CO (1) | CO5550420A2 (ja) |
| CZ (1) | CZ305034B6 (ja) |
| DE (1) | DE60202216T2 (ja) |
| DK (1) | DK1412341T3 (ja) |
| EA (1) | EA006446B1 (ja) |
| ES (1) | ES2233834T3 (ja) |
| HK (2) | HK1068627A1 (ja) |
| HR (1) | HRP20031075B1 (ja) |
| HU (1) | HU228476B1 (ja) |
| IL (1) | IL159229A0 (ja) |
| IS (1) | IS2426B (ja) |
| JO (1) | JO2389B1 (ja) |
| MA (1) | MA26260A1 (ja) |
| ME (2) | MEP1508A (ja) |
| MX (1) | MXPA03011770A (ja) |
| MY (1) | MY133471A (ja) |
| NO (2) | NO329873B1 (ja) |
| NZ (1) | NZ530104A (ja) |
| PE (1) | PE20030122A1 (ja) |
| PL (1) | PL366560A1 (ja) |
| PT (1) | PT1412341E (ja) |
| RS (1) | RS50673B (ja) |
| SI (1) | SI1412341T1 (ja) |
| SK (1) | SK287696B6 (ja) |
| TN (1) | TNSN02062A1 (ja) |
| TW (1) | TWI236473B (ja) |
| UA (1) | UA75147C2 (ja) |
| UY (2) | UY27356A1 (ja) |
| WO (1) | WO2003000672A1 (ja) |
| ZA (1) | ZA200309633B (ja) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI306846B (en) | 2002-08-12 | 2009-03-01 | Lundbeck & Co As H | Method for the separation of intermediates which may be used for the preparation of escitalopram |
| DE60319739T2 (de) | 2002-12-23 | 2008-07-17 | H. Lundbeck A/S, Valby | Escitalopramhydrobromid und ein verfahren zu dessen herstellung |
| PL207847B1 (pl) | 2002-12-23 | 2011-02-28 | Lundbeck & Co As H | Sposób wytwarzania racemicznego 4-[4-(dimetyloamino)-1-(4'-fluorofenylo)-1- hydroksybutylo]-3-(hydroksymetylo)-benzonitrylu) i /lub R-lub S-4-[4-(dimetyloamino)-1-(4'-fluorofenylo)-1-hydroksybutylo]-3-( hydroksymetylo)- benzonitrylu) i sposób wytwarzania racemicznego citalopramu, R-citalopramu i/lub S-citalopramu |
| PT1581483E (pt) * | 2002-12-23 | 2012-07-24 | Lundbeck & Co As H | Processo para a preparação de diol de citalopram racécmico e/ou dos dióis de s- ou r-citalopram e a utilização desses dióis para a preparação de citalopram racémico, rcitalopram e/ou s-citalopram |
| 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 |
| AU2005218713B2 (en) * | 2004-03-05 | 2009-11-19 | 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 |
| EP1797060A2 (en) * | 2004-08-23 | 2007-06-20 | Sun Pharmaceutical Industries Limited | "process for preparation of citalopram and enantiomers" |
| US7989645B2 (en) * | 2004-08-23 | 2011-08-02 | Sun Pharma Global Fze | Process for preparation of citalopram and enantiomers |
| EP1901714A2 (en) * | 2005-05-20 | 2008-03-26 | Aurobindo Pharma Limited | Pharmaceutical dosage forms comprising escitalopram in form of granules |
| 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 |
| BRPI0617382A2 (pt) | 2005-10-14 | 2017-07-11 | H Lundbeck As | Métodos para tratar um distúrbio do sistema nervoso central em um paciente, para tratar um paciente sofrendo de condições e uma disfunção sexual, e para reduzir um retardo na eficácia terapêutica em seguida ao início do tratamento |
| 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)
| 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 |
| DK1298124T3 (da) * | 1999-10-25 | 2007-07-09 | Lundbeck & Co As H | Fremgangsmåde til fremstilling af citalopram |
-
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 TN TNTNSN02062A patent/TNSN02062A1/en unknown
- 2002-06-24 PE PE2002000551A patent/PE20030122A1/es active IP Right Grant
- 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 UY UY27356A patent/UY27356A1/es not_active IP Right Cessation
- 2002-06-25 CZ CZ2004-131A patent/CZ305034B6/cs not_active IP Right Cessation
- 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 CA CA2450890A patent/CA2450890C/en not_active Expired - Fee Related
- 2002-06-25 UA UA20031211986A patent/UA75147C2/uk unknown
- 2002-06-25 SI SI200230078T patent/SI1412341T1/xx unknown
- 2002-06-25 PT PT02742848T patent/PT1412341E/pt unknown
- 2002-06-25 KR KR1020107006751A patent/KR20100052550A/ko not_active Application Discontinuation
- 2002-06-25 ES ES02742848T patent/ES2233834T3/es not_active Expired - Lifetime
- 2002-06-25 CN CNB028126688A patent/CN100429208C/zh not_active Expired - Lifetime
- 2002-06-25 ME MEP-15/08A patent/MEP1508A/xx unknown
- 2002-06-25 MX MXPA03011770A patent/MXPA03011770A/es active IP Right Grant
- 2002-06-25 DE DE60202216T patent/DE60202216T2/de not_active Expired - Lifetime
- 2002-06-25 WO PCT/DK2002/000426 patent/WO2003000672A1/en active Application Filing
- 2002-06-25 HU HU0400293A patent/HU228476B1/hu unknown
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