NL1017525C1 - Werkwijze voor de bereiding van zuiver Citalopram - Google Patents

Werkwijze voor de bereiding van zuiver Citalopram Download PDF

Info

Publication number: NL1017525C1
Authority: NL; Netherlands
Prior art keywords: amide; citalopram; group; cyanide; process according
Prior art date: 2000-12-22

Application number

NL1017525A

Other languages

English (en)

Dutch (nl)

Inventor

Marco Villa

Robert Dancer

Federico Sbrogi

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.)

2000-12-22

Filing date

2001-03-07

Publication date

2001-04-26

2001-03-07 Application filed by Lundbeck & Co As H filed Critical Lundbeck & Co As H

2001-04-26 Application granted granted Critical

2001-04-26 Publication of NL1017525C1 publication Critical patent/NL1017525C1/nl

2001-06-22 Priority to NL1018360A priority Critical patent/NL1018360C1/nl

Links

WSEQXVZVJXJVFP-HXUWFJFHSA-N (R)-citalopram Chemical compound C1([C@@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WSEQXVZVJXJVFP-HXUWFJFHSA-N 0.000 title claims abstract description 42
229960001653 citalopram Drugs 0.000 title claims abstract description 42
238000002360 preparation method Methods 0.000 title claims abstract description 12
238000000034 method Methods 0.000 title claims description 31
238000006243 chemical reaction Methods 0.000 claims abstract description 29
150000001408 amides Chemical class 0.000 claims abstract description 20
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical group N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims abstract description 17
239000003795 chemical substances by application Substances 0.000 claims abstract description 15
229910052794 bromium Inorganic materials 0.000 claims abstract description 11
239000002253 acid Substances 0.000 claims abstract description 10
229910052801 chlorine Inorganic materials 0.000 claims abstract description 10
239000000203 mixture Substances 0.000 claims abstract description 10
150000003839 salts Chemical class 0.000 claims abstract description 10
125000000217 alkyl group Chemical group 0.000 claims abstract description 8
239000011541 reaction mixture Substances 0.000 claims abstract description 8
150000001875 compounds Chemical class 0.000 claims abstract description 7
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 6
238000000746 purification Methods 0.000 claims abstract description 6
229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
229910052736 halogen Inorganic materials 0.000 claims abstract description 5
229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 3
125000003107 substituted aryl group Chemical group 0.000 claims abstract 2
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical group CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 15
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 14
239000002904 solvent Substances 0.000 claims description 12
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 10
239000003054 catalyst Substances 0.000 claims description 9
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
239000000460 chlorine Substances 0.000 claims description 8
239000010949 copper Substances 0.000 claims description 6
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 5
229910052763 palladium Inorganic materials 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
230000003197 catalytic effect Effects 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 claims description 3
150000002367 halogens Chemical group 0.000 claims description 3
229910052721 tungsten Inorganic materials 0.000 claims description 3
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 2
239000012346 acetyl chloride Substances 0.000 claims description 2
150000001263 acyl chlorides Chemical group 0.000 claims 1
150000001266 acyl halides Chemical class 0.000 claims 1
150000001244 carboxylic acid anhydrides Chemical group 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 claims 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
239000000047 product Substances 0.000 abstract description 12
239000012535 impurity Substances 0.000 abstract description 6
238000002425 crystallisation Methods 0.000 abstract description 4
230000008025 crystallization Effects 0.000 abstract description 4
125000005843 halogen group Chemical group 0.000 abstract description 3
229910052740 iodine Inorganic materials 0.000 abstract description 3
238000001953 recrystallisation Methods 0.000 abstract description 3
PTJADDMMFYXMMG-LJQANCHMSA-N (1r)-1-(4-fluorophenyl)-1-[3-(methylamino)propyl]-3h-2-benzofuran-5-carbonitrile Chemical compound C1([C@@]2(C3=CC=C(C=C3CO2)C#N)CCCNC)=CC=C(F)C=C1 PTJADDMMFYXMMG-LJQANCHMSA-N 0.000 abstract 1
239000012043 crude product Substances 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
239000002585 base Substances 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
239000012074 organic phase Substances 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000000654 additive Substances 0.000 description 6
150000002825 nitriles Chemical group 0.000 description 6
239000012071 phase Substances 0.000 description 6
239000000243 solution Substances 0.000 description 6
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
VMJNTFXCTXAXTC-UHFFFAOYSA-N 2,2-difluoro-1,3-benzodioxole-5-carbonitrile Chemical group C1=C(C#N)C=C2OC(F)(F)OC2=C1 VMJNTFXCTXAXTC-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
PTJADDMMFYXMMG-UHFFFAOYSA-N Demethylcitalopram Chemical class O1CC2=CC(C#N)=CC=C2C1(CCCNC)C1=CC=C(F)C=C1 PTJADDMMFYXMMG-UHFFFAOYSA-N 0.000 description 4
-1 5-thiazolinyl group Chemical group 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
238000011109 contamination Methods 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
239000007924 injection Substances 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000008194 pharmaceutical composition Substances 0.000 description 3
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 3
WSEQXVZVJXJVFP-UHFFFAOYSA-N 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile Chemical compound O1CC2=CC(C#N)=CC=C2C1(CCCN(C)C)C1=CC=C(F)C=C1 WSEQXVZVJXJVFP-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
230000001430 anti-depressive effect Effects 0.000 description 2
239000000935 antidepressant agent Substances 0.000 description 2
229940005513 antidepressants Drugs 0.000 description 2
239000003125 aqueous solvent Substances 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
239000012458 free base Substances 0.000 description 2
239000011630 iodine Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 2
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
239000003826 tablet Substances 0.000 description 2
238000005406 washing Methods 0.000 description 2
238000010626 work up procedure Methods 0.000 description 2
CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
YXCRMKYHFFMNPT-UHFFFAOYSA-N 1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile Chemical compound C1=CC(F)=CC=C1C1C2=CC=C(C#N)C=C2CO1 YXCRMKYHFFMNPT-UHFFFAOYSA-N 0.000 description 1
SWWQQSDRUYSMAR-UHFFFAOYSA-N 1-[(4-hydroxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol;hydrochloride Chemical group Cl.C1=CC(O)=CC=C1CC1C2=CC(O)=C(O)C=C2CCN1 SWWQQSDRUYSMAR-UHFFFAOYSA-N 0.000 description 1
WOLPGGGWZDXCNM-UHFFFAOYSA-N 3-[5-bromo-1-(4-fluorophenyl)-3h-2-benzofuran-1-yl]-n,n-dimethylpropan-1-amine Chemical compound O1CC2=CC(Br)=CC=C2C1(CCCN(C)C)C1=CC=C(F)C=C1 WOLPGGGWZDXCNM-UHFFFAOYSA-N 0.000 description 1
GHZPDRVHYHFILK-UHFFFAOYSA-N 3-chloro-3h-2-benzofuran-1-one Chemical compound C1=CC=C2C(Cl)OC(=O)C2=C1 GHZPDRVHYHFILK-UHFFFAOYSA-N 0.000 description 1
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
206010012289 Dementia Diseases 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
208000026106 cerebrovascular disease Diseases 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
239000000975 dye Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
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 1
229960004341 escitalopram Drugs 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000011049 filling Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000003205 fragrance Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
229910000069 nitrogen hydride Inorganic materials 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000003825 pressing Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229940076279 serotonin Drugs 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
229910052727 yttrium Inorganic materials 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
- A61P25/24—Antidepressants

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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)
Psychiatry (AREA)
Medicinal Chemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Pain & Pain Management (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

NL1017525A 2000-12-22 2001-03-07 Werkwijze voor de bereiding van zuiver Citalopram NL1017525C1 (nl)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
NL1018360A NL1018360C1 (nl)	2000-12-22	2001-06-22	Werkwijze voor de bereiding van zuiver Citalopram.

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DK200001929		2000-12-22
DKPA200001929		2000-12-22

Publications (1)

Publication Number	Publication Date
NL1017525C1 true NL1017525C1 (nl)	2001-04-26

Family

ID=8159922

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
NL1017525A NL1017525C1 (nl)	2000-12-22	2001-03-07	Werkwijze voor de bereiding van zuiver Citalopram
NL1018360A NL1018360C1 (nl)	2000-12-22	2001-06-22	Werkwijze voor de bereiding van zuiver Citalopram.

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
NL1018360A NL1018360C1 (nl)	2000-12-22	2001-06-22	Werkwijze voor de bereiding van zuiver Citalopram.

Country Status (43)

Country	Link
US (1)	US6455710B1 (bg)
EP (2)	EP1181713B1 (bg)
JP (1)	JP3798982B2 (bg)
KR (1)	KR100439329B1 (bg)
CN (1)	CN1282648C (bg)
AR (1)	AR030056A1 (bg)
AT (2)	ATE277920T1 (bg)
AU (2)	AU2001100405B4 (bg)
BE (2)	BE1013212A6 (bg)
BG (1)	BG65131B1 (bg)
BR (1)	BR0106272A (bg)
CA (1)	CA2360303C (bg)
CH (1)	CH691535A5 (bg)
CZ (1)	CZ292200B6 (bg)
DE (2)	DE60105926T2 (bg)
DK (1)	DK1181713T3 (bg)
EA (1)	EA003581B1 (bg)
ES (2)	ES2228824T3 (bg)
FI (2)	FI108639B (bg)
FR (1)	FR2812877B1 (bg)
GB (1)	GB2357763B (bg)
GR (1)	GR1003874B (bg)
HK (1)	HK1048812B (bg)
HR (1)	HRP20020004A2 (bg)
HU (2)	HU0101029D0 (bg)
IE (1)	IES20010254A2 (bg)
IL (1)	IL147226A (bg)
IS (1)	IS2060B (bg)
IT (1)	ITMI20010602A1 (bg)
MX (1)	MXPA01013151A (bg)
NL (2)	NL1017525C1 (bg)
NO (1)	NO20011271A (bg)
NZ (1)	NZ516298A (bg)
PL (1)	PL205724B1 (bg)
PT (1)	PT1181713E (bg)
SE (1)	SE517623C2 (bg)
SG (1)	SG167655A1 (bg)
SI (1)	SI1181713T1 (bg)
SK (2)	SK284428B6 (bg)
TR (1)	TR200201166T1 (bg)
UA (1)	UA71634C2 (bg)
WO (1)	WO2001045483A2 (bg)
ZA (1)	ZA200110179B (bg)

Families Citing this family (30)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AR022329A1 (es)	1999-01-29	2002-09-04	Lundbeck & Co As H	Metodo para la preparacion de 5-cianoftalida
DE69907037T3 (de)	1999-04-14	2010-02-18	H. Lundbeck A/S	Verfahren zur herstellung von citalopram
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2001
- 2001-03-07 TR TR2002/01166T patent/TR200201166T1/xx unknown
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Publication number	Publication date
HK1048812B (zh)	2007-06-01
ATE277920T1 (de)	2004-10-15
FI20010500A0 (fi)	2001-03-13
ZA200110179B (en)	2002-12-11
DE10112829C1 (de)	2002-07-25
PL205724B1 (pl)	2010-05-31
EA200200018A1 (ru)	2002-04-25
DE60105926D1 (de)	2004-11-04
KR100439329B1 (ko)	2004-07-07
FR2812877B1 (fr)	2003-04-04
GB2357763B (en)	2002-01-16
HU0101029D0 (en)	2001-05-28
SG167655A1 (en)	2011-01-28
FR2812877A1 (fr)	2002-02-15
JP3798982B2 (ja)	2006-07-19
CH691535A5 (de)	2001-08-15
NL1018360C1 (nl)	2001-10-04
IS5883A (is)	2001-06-20
JP2003517484A (ja)	2003-05-27
US20020120005A1 (en)	2002-08-29
BG106203A (bg)	2002-08-30
CN1282648C (zh)	2006-11-01
HRP20020004A2 (en)	2003-04-30
ITMI20010602A1 (it)	2002-09-22
SK284428B6 (sk)	2005-04-01
SK18482001A3 (sk)	2002-05-09
GB0105983D0 (en)	2001-05-02
HUP0102817A3 (en)	2003-07-28
WO2001045483A3 (en)	2001-12-27
EP1181713B1 (en)	2004-09-29
IL147226A0 (en)	2002-08-14
TR200201166T1 (tr)	2002-10-21
BE1013212A6 (fr)	2001-10-02
DE60105926T2 (de)	2005-11-24
CZ292200B6 (cs)	2003-08-13
NO312462B1 (no)	2002-05-13
CA2360303C (en)	2003-08-12
ES2170732B2 (es)	2003-09-16
EA003581B1 (ru)	2003-06-26
ES2228824T3 (es)	2005-04-16
GB2357763A (en)	2001-07-04
US6455710B1 (en)	2002-09-24
FI108639B (fi)	2002-02-28
IL147226A (en)	2006-04-10
SE517623C2 (sv)	2002-06-25
GR1003874B (el)	2002-04-24
SI1181713T1 (en)	2005-02-28
BG65131B1 (bg)	2007-03-30
AR030056A1 (es)	2003-08-13
SE0103045D0 (sv)	2001-09-14
NZ516298A (en)	2002-12-20
NO20011271D0 (no)	2001-03-13
CZ2001890A3 (cs)	2002-08-14
HU0102817D0 (en)	2001-09-28
NO20011271A (no)	2002-05-13
CA2360303A1 (en)	2001-06-28
UA71634C2 (uk)	2004-12-15
BE1013213A6 (fr)	2001-10-02
MXPA01013151A (es)	2002-08-12
SK286283B6 (sk)	2008-06-06
WO2001045483A2 (en)	2001-06-28
AU2001100405A4 (en)	2001-11-01
IES20010254A2 (en)	2002-03-06
PT1181713E (pt)	2005-02-28
EP1462447A3 (en)	2004-11-17
AT4367U1 (de)	2001-06-25
AU2001100405B4 (en)	2002-03-21
PL353398A1 (en)	2003-11-17
SE0103045L (sv)	2002-06-23
EP1462447A2 (en)	2004-09-29
EP1181713A2 (en)	2002-02-27
FI20011577A0 (fi)	2001-07-26
ES2170732A1 (es)	2002-08-01
CN1366525A (zh)	2002-08-28
HK1048812A1 (en)	2003-04-17
AU3920101A (en)	2001-07-03
DK1181713T3 (da)	2005-01-31
KR20020065345A (ko)	2002-08-13
HUP0102817A2 (hu)	2001-12-28
IS2060B (is)	2005-11-15
ITMI20010602A0 (it)	2001-03-22
BR0106272A (pt)	2004-06-15

Publication	Publication Date	Title
NL1017525C1 (nl)	2001-04-26	Werkwijze voor de bereiding van zuiver Citalopram
AU2001100399A4 (en)	2001-11-01	Process for the preparation of pure citalopram
NL1018410C1 (nl)	2001-11-13	Werkwijze voor de bereiding van zuiver Citalopram.
AU744112B1 (en)	2002-02-14	Process for the preparation of pure citalopram
GB2359811A (en)	2001-09-05	Purification of citalopram by acylation of the methylamino group of the desmethyl citalopram impurity & subsequent removal of the ensuing amide
DK174018B1 (da)	2002-04-22	Proces til fjernelse af desmethyl citalopram fra et citalopram produkt
CH691998A5 (de)	2001-12-31	Verfahren zur Herstellung von reinem Citalopram.
AT4681U1 (de)	2001-10-25	Verfahren zur herstellung von reinem citalopram

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2007-05-01	VD2	Discontinued due to expiration of the term of protection	Effective date: 20070307