SE516690C2 - Förfarande för framställning av citalopram - Google Patents

Förfarande för framställning av citalopram

Info

Publication number: SE516690C2
Authority: SE; Sweden
Prior art keywords: formula; compound; citalopram; process according; palladium catalyst
Prior art date: 1999-06-25

Application number

SE0100193A

Other languages

English (en)

Swedish (sv)

Other versions

SE0100193D0 (sv

SE0100193L (sv

Inventor

Hans Petersen

Michael Harold Rock

Henrik Svane

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.)

1999-06-25

Filing date

2001-01-24

Publication date

2002-02-12

2001-01-24 Application filed by Lundbeck & Co As H filed Critical Lundbeck & Co As H

2001-01-24 Publication of SE0100193D0 publication Critical patent/SE0100193D0/xx

2001-04-25 Publication of SE0100193L publication Critical patent/SE0100193L/xx

2002-02-12 Publication of SE516690C2 publication Critical patent/SE516690C2/sv

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 18
229960001653 citalopram Drugs 0.000 title claims abstract description 18
238000002360 preparation method Methods 0.000 title claims abstract description 8
238000000034 method Methods 0.000 title claims description 30
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 37
-1 isobenzofuran compound Chemical class 0.000 claims abstract description 16
239000003054 catalyst Substances 0.000 claims abstract description 15
229910052763 palladium Inorganic materials 0.000 claims abstract description 13
150000003839 salts Chemical class 0.000 claims abstract description 13
230000003197 catalytic effect Effects 0.000 claims abstract description 8
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims abstract description 7
150000001875 compounds Chemical class 0.000 claims description 15
238000006243 chemical reaction Methods 0.000 claims description 12
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
229910052794 bromium Inorganic materials 0.000 claims description 7
MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 claims 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 claims description 6
101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 claims description 5
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
229910052740 iodine Chemical group 0.000 claims description 4
239000011630 iodine Chemical group 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
125000001246 bromo group Chemical group Br* 0.000 claims description 3
238000002955 isolation Methods 0.000 claims description 3
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 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical group 0.000 claims 1
239000010949 copper Substances 0.000 abstract description 6
150000002500 ions Chemical class 0.000 abstract description 3
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 2
229910052802 copper Inorganic materials 0.000 abstract 2
239000011701 zinc Substances 0.000 abstract 2
229910052725 zinc Inorganic materials 0.000 abstract 2
GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 abstract 2
125000005843 halogen group Chemical group 0.000 abstract 1
125000002346 iodo group Chemical group I* 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
239000011541 reaction mixture Substances 0.000 description 13
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
239000000243 solution Substances 0.000 description 9
239000002904 solvent Substances 0.000 description 9
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
239000000543 intermediate Substances 0.000 description 7
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
KTGRHKOEFSJQNS-UHFFFAOYSA-N Citalopram Oxalate Chemical compound OC(=O)C(O)=O.O1CC2=CC(C#N)=CC=C2C1(CCCN(C)C)C1=CC=C(F)C=C1 KTGRHKOEFSJQNS-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 6
238000007363 ring formation reaction Methods 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
239000002253 acid Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
229910052786 argon Inorganic materials 0.000 description 4
239000012458 free base Substances 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 3
238000003747 Grignard reaction Methods 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
239000000654 additive Substances 0.000 description 3
239000002671 adjuvant Substances 0.000 description 3
239000002585 base Substances 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
239000003480 eluent Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
238000002347 injection Methods 0.000 description 3
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
239000003826 tablet Substances 0.000 description 3
AITNMTXHTIIIBB-UHFFFAOYSA-N 1-bromo-4-fluorobenzene Chemical compound FC1=CC=C(Br)C=C1 AITNMTXHTIIIBB-UHFFFAOYSA-N 0.000 description 2
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 2
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 2
NYYRRBOMNHUCLB-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCCl NYYRRBOMNHUCLB-UHFFFAOYSA-N 0.000 description 2
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
PZZLBLVQBCCSLT-UHFFFAOYSA-N C(C(=O)O)(=O)O.CN(CCCC1(OCC2=CC(=CC=C12)O)C1=CC=C(C=C1)F)C Chemical compound C(C(=O)O)(=O)O.CN(CCCC1(OCC2=CC(=CC=C12)O)C1=CC=C(C=C1)F)C PZZLBLVQBCCSLT-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
230000000996 additive effect Effects 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
239000012267 brine Substances 0.000 description 2
230000005587 bubbling Effects 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
238000001816 cooling Methods 0.000 description 2
DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 2
125000004093 cyano group Chemical group *C#N 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000005457 ice water 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
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
BRKADVNLTRCLOW-UHFFFAOYSA-M magnesium;fluorobenzene;bromide Chemical compound [Mg+2].[Br-].FC1=CC=[C-]C=C1 BRKADVNLTRCLOW-UHFFFAOYSA-M 0.000 description 2
150000003891 oxalate salts Chemical class 0.000 description 2
235000006408 oxalic acid Nutrition 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000012071 phase Substances 0.000 description 2
SFLGSKRGOWRGBR-UHFFFAOYSA-N phthalane Chemical class C1=CC=C2COCC2=C1 SFLGSKRGOWRGBR-UHFFFAOYSA-N 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
XEEGWTLAFIZLSF-UHFFFAOYSA-N 1-oxo-3h-2-benzofuran-5-carbonitrile Chemical compound N#CC1=CC=C2C(=O)OCC2=C1 XEEGWTLAFIZLSF-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
IUSPXLCLQIZFHL-UHFFFAOYSA-N 5-bromo-3h-2-benzofuran-1-one Chemical compound BrC1=CC=C2C(=O)OCC2=C1 IUSPXLCLQIZFHL-UHFFFAOYSA-N 0.000 description 1
QJEJYBQYGQJKSK-UHFFFAOYSA-N 5-hydroxy-3h-2-benzofuran-1-one Chemical compound OC1=CC=C2C(=O)OCC2=C1 QJEJYBQYGQJKSK-UHFFFAOYSA-N 0.000 description 1
CQAKANQMFXBJJQ-UHFFFAOYSA-N 5-iodo-3h-2-benzofuran-1-one Chemical compound IC1=CC=C2C(=O)OCC2=C1 CQAKANQMFXBJJQ-UHFFFAOYSA-N 0.000 description 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
244000144725 Amygdalus communis Species 0.000 description 1
235000011437 Amygdalus communis Nutrition 0.000 description 1
DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
244000223760 Cinnamomum zeylanicum Species 0.000 description 1
235000005979 Citrus limon Nutrition 0.000 description 1
244000131522 Citrus pyriformis Species 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 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
241000220225 Malus Species 0.000 description 1
235000011430 Malus pumila Nutrition 0.000 description 1
235000015103 Malus silvestris Nutrition 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
RCRFWIYICXMPKN-UHFFFAOYSA-N [1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-3h-2-benzofuran-5-yl] trifluoromethanesulfonate Chemical compound O1CC2=CC(OS(=O)(=O)C(F)(F)F)=CC=C2C1(CCCN(C)C)C1=CC=C(F)C=C1 RCRFWIYICXMPKN-UHFFFAOYSA-N 0.000 description 1
ALIGTYPNWJPIKT-UHFFFAOYSA-M [Cl-].FC1=CC=C([Mg+])C=C1 Chemical compound [Cl-].FC1=CC=C([Mg+])C=C1 ALIGTYPNWJPIKT-UHFFFAOYSA-M 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
125000000218 acetic acid group Chemical class C(C)(=O)* 0.000 description 1
235000020224 almond Nutrition 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
239000000935 antidepressant agent Substances 0.000 description 1
229940005513 antidepressants Drugs 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
229960001230 asparagine Drugs 0.000 description 1
235000009582 asparagine Nutrition 0.000 description 1
TWJVNKMWXNTSAP-UHFFFAOYSA-N azanium;hydroxide;hydrochloride Chemical compound [NH4+].O.[Cl-] TWJVNKMWXNTSAP-UHFFFAOYSA-N 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
235000017803 cinnamon Nutrition 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
239000013058 crude material Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
150000002148 esters Chemical class 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
239000000796 flavoring agent Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 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
229910001385 heavy metal Inorganic materials 0.000 description 1
150000002440 hydroxy compounds Chemical class 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
150000002497 iodine compounds Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
NGPAITITALWALP-UHFFFAOYSA-M magnesium;n,n-dimethylpropan-1-amine;chloride Chemical compound [Mg+2].[Cl-].CN(C)CC[CH2-] NGPAITITALWALP-UHFFFAOYSA-M 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
150000002825 nitriles Chemical group 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
238000000926 separation method Methods 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
229910052717 sulfur Inorganic materials 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
239000012485 toluene extract Substances 0.000 description 1
GRGCWBWNLSTIEN-UHFFFAOYSA-N trifluoromethanesulfonyl chloride Chemical compound FC(F)(F)S(Cl)(=O)=O GRGCWBWNLSTIEN-UHFFFAOYSA-N 0.000 description 1
235000021419 vinegar Nutrition 0.000 description 1
239000000052 vinegar Substances 0.000 description 1
238000010626 work up procedure Methods 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
- A61K31/343—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide condensed with a carbocyclic ring, e.g. coumaran, bufuralol, befunolol, clobenfurol, amiodarone
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/44—Palladium
- 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
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/81—Radicals substituted by nitrogen atoms not forming part of a nitro radical

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
General Chemical & Material Sciences (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Pain & Pain Management (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Materials Engineering (AREA)
Rheumatology (AREA)
Psychiatry (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Catalysts (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Steroid Compounds (AREA)

SE0100193A 1999-06-25 2001-01-24 Förfarande för framställning av citalopram SE516690C2 (sv)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DKPA199900920		1999-06-25
PCT/DK1999/000640 WO2000013648A2 (en)	1999-06-25	1999-11-22	Method for the preparation of citalopram

Publications (3)

Publication Number	Publication Date
SE0100193D0 SE0100193D0 (sv)	2001-01-24
SE0100193L SE0100193L (sv)	2001-04-25
SE516690C2 true SE516690C2 (sv)	2002-02-12

Family

ID=8099035

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE0100193A SE516690C2 (sv)	1999-06-25	2001-01-24	Förfarande för framställning av citalopram

Country Status (36)

Country	Link
US (2)	US20020077353A1 (de)
EP (1)	EP1159274B1 (de)
JP (1)	JP3447267B2 (de)
KR (1)	KR100491368B1 (de)
CN (2)	CN1140521C (de)
AR (1)	AR020863A1 (de)
AT (3)	AT409961B (de)
AU (2)	AU2001100440B4 (de)
BG (1)	BG65574B1 (de)
BR (1)	BR9917368B1 (de)
CA (2)	CA2290127C (de)
CH (1)	CH691305A5 (de)
CZ (1)	CZ292198B6 (de)
DE (2)	DE69906389T2 (de)
DK (2)	DK1159274T3 (de)
EA (1)	EA002560B1 (de)
ES (2)	ES2194545T3 (de)
FI (1)	FI108641B (de)
GB (2)	GB2354239B (de)
HK (1)	HK1049002B (de)
HU (1)	HUP0103235A3 (de)
IL (2)	IL145959A0 (de)
IS (1)	IS2343B (de)
IT (1)	ITMI991581A1 (de)
MX (1)	MXPA01010989A (de)
NO (1)	NO328542B1 (de)
NZ (1)	NZ514979A (de)
PL (1)	PL205579B1 (de)
PT (1)	PT1159274E (de)
SE (1)	SE516690C2 (de)
SI (1)	SI1159274T1 (de)
SK (1)	SK285813B6 (de)
TR (1)	TR200103702T2 (de)
UA (1)	UA63034C2 (de)
WO (1)	WO2000013648A2 (de)
ZA (1)	ZA200108854B (de)

Families Citing this family (37)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HK1043130B (zh)	1998-12-23	2005-03-04	H‧隆德贝克有限公司	制备5-氰基2-苯并[c]呋喃酮的方法
AR022329A1 (es)	1999-01-29	2002-09-04	Lundbeck & Co As H	Metodo para la preparacion de 5-cianoftalida
IL145615A0 (en)	1999-04-14	2002-06-30	Lundbeck & Co As H	Method for the preparation of citalopram
ITMI991579A1 (it)	1999-06-25	2001-01-15	Lundbeck & Co As H	Metodo per la preparazione di citalopram
HK1043129B (zh)	1999-10-25	2004-10-21	H‧隆德贝克有限公司	西酞普蘭的製備方法
GB2360281B (en)	1999-10-25	2002-01-16	Lundbeck & Co As H	Method for the preparation of citalopram
AR026063A1 (es)	1999-11-01	2002-12-26	Lundbeck & Co As H	Metodo para la preparacion de 5-carboxiftalida.
NZ519739A (en)	1999-12-28	2004-03-26	H	Method for the preparation of citalopram
PT1246813E (pt)	1999-12-30	2004-02-27	Lundbeck & Co As H	Metodo para a preparacao de citalopram
WO2001051477A1 (en)	2000-01-14	2001-07-19	H. Lundbeck A/S	Method for the preparation of 5-cyanophthalide
NL1017415C1 (nl)	2000-02-24	2001-05-18	Lundbeck & Co As H	Werkwijze voor de bereiding van Citalopram.
IES20010157A2 (en)	2000-03-03	2002-03-06	Lundbeck & Co As H	Method for the preparation of citalopram
GB2357762B (en) *	2000-03-13	2002-01-30	Lundbeck & Co As H	Crystalline base of citalopram
NL1017500C1 (nl)	2000-03-13	2001-04-26	Lundbeck & Co As H	Werkwijze voor de bereiding van Citalopram.
SK14602002A3 (sk)	2000-03-13	2003-02-04	H. Lundbeck A/S	Spôsob výroby citalopramu a medziprodukty
BR0109364A (pt)	2000-03-13	2002-12-24	Lundbeck & Co As H	Métodos para fabricação de citalopram através de alquilação escalonada de 5-substituìda 1- (4-fluorofenil) - 1,3- diidroisobenzofuranos e citalopram
IL151488A0 (en)	2000-03-14	2003-04-10	Lundbeck & Co As H	Method for the preparation of citalopram
TR200202168T2 (tr) *	2000-03-16	2002-12-23	H. Lundbeck A/S	5-Siyano-1-(4-Florofenil)-1,3-Dihidroizobenzofuranların preparasyon metodu
AR032455A1 (es)	2000-05-12	2003-11-12	Lundbeck & Co As H	Metodo para la preparacion de citalopram, un intermediario empleado en el metodo, un metodo para la preparacion del intermediario empleado en el metodo y composicion farmaceutica antidepresiva
SK3362002A3 (en) *	2000-07-06	2002-08-06	Lundbeck & Co As H	Method for the preparation of citalopram
IL144816A (en) *	2000-08-18	2005-09-25	Lundbeck & Co As H	Method for the preparation of citalopram
TR200201166T1 (tr) *	2000-12-22	2002-10-21	H.Lundbecks A/S	Saf sitalopram hazırlanması için yöntem
JP2003519121A (ja) *	2000-12-28	2003-06-17	ハー・ルンドベック・アクチエゼルスカベット	純粋なシタロプラムの製造方法
CA2435925A1 (en)	2001-01-30	2002-08-08	Orion Corporation Fermion	Process for the preparation of 1-(3-dimethylaminopropyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile
GB0105627D0 (en) *	2001-03-07	2001-04-25	Cipla Ltd	Preparation of phthalanes
HRP20030811A2 (en) *	2001-03-09	2005-08-31	Ranbaxy Laboratories Limited	Process for the preparation of citalopram
US6967259B2 (en) *	2001-09-24	2005-11-22	Pharmachem Technologies Limited	Process for the preparation of Citalopram intermediate
WO2003057132A2 (en) *	2002-01-07	2003-07-17	Sun Pharmaceutical Industries Limited	Process for the preparation of 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)- 1,3-dihydro-5-isobenzofuran carbonitrile
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
AU2003223105A1 (en) *	2003-03-24	2004-10-18	Hetero Drugs Limited	Novel crystalline forms of (s)-citalopram oxalate
EP1486492A3 (de)	2003-06-10	2005-02-23	Sun Pharmaceuticals Industries Ltd.	Ein Verfahren zur Hydrogenolyse von [1-(3-dimethylamino)propyl)]-1-(4-fluorophenyl)-1,3-dihydro-5-halo-isobenzofuran
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
KR101166280B1 (ko)	2004-08-23	2013-11-27	썬 파마 글로벌 에프제트이	시탈로프램 및 에난티오머의 제조 방법
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
EP2017271A1 (de)	2007-07-06	2009-01-21	Aurobindo Pharma Limited	Verfahren zur Herstellung von Escitalopram
CN114763343B (zh) *	2021-01-14	2026-02-10	浙江华海药业股份有限公司	一种西酞普兰或s-西酞普兰的纯化方法

Family Cites Families (23)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1143703A (de) *	1965-03-18
GB1526331A (en) *	1976-01-14	1978-09-27	Kefalas As	Phthalanes
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
US5296507A (en) *	1990-09-06	1994-03-22	H.Lundbeck A/S	Treatment of cerbrovascular disorders
DK213290D0 (da) *	1990-09-06	1990-09-06	Lundbeck & Co As H	Treatment of cerebrovascular disorders
DE19626659A1 (de) *	1996-07-03	1998-01-08	Basf Ag	Verfahren zur Herstellung von Phthaliden
DE19627697A1 (de) *	1996-07-10	1998-01-15	Basf Ag	Verfahren zur Herstellung von Phthaliden
JP3526581B2 (ja) *	1997-07-08	2004-05-17	ハー・ルンドベック・アクティーゼルスカブ	シタロプラムの製造方法
UA62985C2 (en) *	1997-11-10	2004-01-15	Lunnbeck As H	A method for the preparation of citalopram
CN1286687A (zh) *	1997-11-11	2001-03-07	H·隆德贝克有限公司	制备西酞普兰的方法
WO2000023431A1 (en) *	1998-10-20	2000-04-27	H. Lundbeck A/S	Method for the preparation of citalopram
HK1043130B (zh) *	1998-12-23	2005-03-04	H‧隆德贝克有限公司	制备5-氰基2-苯并[c]呋喃酮的方法
AR022329A1 (es) *	1999-01-29	2002-09-04	Lundbeck & Co As H	Metodo para la preparacion de 5-cianoftalida
IL145615A0 (en) *	1999-04-14	2002-06-30	Lundbeck & Co As H	Method for the preparation of citalopram
ITMI991579A1 (it) *	1999-06-25	2001-01-15	Lundbeck & Co As H	Metodo per la preparazione di citalopram
GB2360281B (en) *	1999-10-25	2002-01-16	Lundbeck & Co As H	Method for the preparation of citalopram
AR026063A1 (es) *	1999-11-01	2002-12-26	Lundbeck & Co As H	Metodo para la preparacion de 5-carboxiftalida.
NL1017415C1 (nl) *	2000-02-24	2001-05-18	Lundbeck & Co As H	Werkwijze voor de bereiding van Citalopram.
IES20010143A2 (en) *	2000-02-24	2001-07-25	Lundbeck & Co As H	Method for the preparation of citalopram
IL144816A (en) *	2000-08-18	2005-09-25	Lundbeck & Co As H	Method for the preparation of citalopram
TR200201166T1 (tr) *	2000-12-22	2002-10-21	H.Lundbecks A/S	Saf sitalopram hazırlanması için yöntem
JP2003519121A (ja) *	2000-12-28	2003-06-17	ハー・ルンドベック・アクチエゼルスカベット	純粋なシタロプラムの製造方法

1999
- 1999-07-15 IT IT1999MI001581A patent/ITMI991581A1/it unknown
- 1999-11-22 CA CA002290127A patent/CA2290127C/en not_active Expired - Fee Related
- 1999-11-22 AU AU2001100440A patent/AU2001100440B4/en not_active Expired
- 1999-11-22 CA CA002475401A patent/CA2475401A1/en not_active Abandoned
- 1999-11-22 PL PL346237A patent/PL205579B1/pl not_active IP Right Cessation
- 1999-11-22 GB GB0101504A patent/GB2354239B/en not_active Expired - Fee Related
- 1999-11-22 IL IL14595999A patent/IL145959A0/xx active IP Right Grant
- 1999-11-22 CN CNB998167517A patent/CN1140521C/zh not_active Expired - Fee Related
- 1999-11-22 KR KR10-2001-7014053A patent/KR100491368B1/ko not_active Expired - Fee Related
- 1999-11-22 HU HU0103235A patent/HUP0103235A3/hu unknown
- 1999-11-22 MX MXPA01010989A patent/MXPA01010989A/es not_active IP Right Cessation
- 1999-11-22 AU AU13745/00A patent/AU1374500A/en active Pending
- 1999-11-22 DE DE69906389T patent/DE69906389T2/de not_active Expired - Lifetime
- 1999-11-22 TR TR2001/03702T patent/TR200103702T2/xx unknown
- 1999-11-22 NZ NZ514979A patent/NZ514979A/en not_active IP Right Cessation
- 1999-11-22 SI SI9930276T patent/SI1159274T1/xx unknown
- 1999-11-22 PT PT99968622T patent/PT1159274E/pt unknown
- 1999-11-22 SK SK1840-2001A patent/SK285813B6/sk not_active IP Right Cessation
- 1999-11-22 CH CH00308/01A patent/CH691305A5/de not_active IP Right Cessation
- 1999-11-22 BR BRPI9917368-9A patent/BR9917368B1/pt not_active IP Right Cessation
- 1999-11-22 DK DK99968622T patent/DK1159274T3/da active
- 1999-11-22 ES ES99968622T patent/ES2194545T3/es not_active Expired - Lifetime
- 1999-11-22 EA EA200101072A patent/EA002560B1/ru not_active IP Right Cessation
- 1999-11-22 AT AT0904199A patent/AT409961B/de not_active IP Right Cessation
- 1999-11-22 JP JP2000568457A patent/JP3447267B2/ja not_active Expired - Fee Related
- 1999-11-22 HK HK03101234.1A patent/HK1049002B/zh not_active IP Right Cessation
- 1999-11-22 EP EP99968622A patent/EP1159274B1/de not_active Expired - Lifetime
- 1999-11-22 AT AT99968622T patent/ATE235478T1/de not_active IP Right Cessation
- 1999-11-22 DE DE19983487A patent/DE19983487C1/de not_active Expired - Fee Related
- 1999-11-22 CN CNA2003101187801A patent/CN1502616A/zh active Pending
- 1999-11-22 CZ CZ2001320A patent/CZ292198B6/cs not_active IP Right Cessation
- 1999-11-22 WO PCT/DK1999/000640 patent/WO2000013648A2/en not_active Ceased
- 1999-11-22 GB GB0105182A patent/GB2357761B/en not_active Expired - Fee Related
- 1999-11-22 UA UA2001118041A patent/UA63034C2/uk unknown
- 1999-11-22 ES ES200150011A patent/ES2189699A1/es not_active Withdrawn
2000
- 2000-06-20 AR ARP000103055A patent/AR020863A1/es active IP Right Grant
2001
- 2001-01-15 DK DK200100060A patent/DK200100060A/da not_active Application Discontinuation
- 2001-01-19 NO NO20010319A patent/NO328542B1/no not_active IP Right Cessation
- 2001-01-24 SE SE0100193A patent/SE516690C2/sv not_active IP Right Cessation
- 2001-01-25 FI FI20010155A patent/FI108641B/fi not_active IP Right Cessation
- 2001-02-23 IS IS5861A patent/IS2343B/is unknown
- 2001-03-13 AT AT0018401U patent/AT4365U1/de not_active IP Right Cessation
- 2001-10-16 IL IL145959A patent/IL145959A/en not_active IP Right Cessation
- 2001-10-26 ZA ZA200108854A patent/ZA200108854B/xx unknown
- 2001-11-06 US US10/012,054 patent/US20020077353A1/en not_active Abandoned
- 2001-12-07 BG BG106191A patent/BG65574B1/bg unknown
2008
- 2008-12-08 US US12/329,750 patent/US20090088469A1/en not_active Abandoned

Also Published As

Publication number	Publication date
CZ292198B6 (cs)	2003-08-13
GB0105182D0 (en)	2001-04-18
NZ514979A (en)	2004-01-30
CH691305A5 (de)	2001-06-29
GB2354239B (en)	2001-06-06
NO328542B1 (no)	2010-03-15
AU1374500A (en)	2000-03-27
AU2001100440B4 (en)	2002-01-24
DE69906389D1 (de)	2003-04-30
DK200100060A (da)	2001-04-10
SK285813B6 (sk)	2007-08-02
US20090088469A1 (en)	2009-04-02
ITMI991581A1 (it)	2001-01-15
ZA200108854B (en)	2002-08-28
JP2002526386A (ja)	2002-08-20
KR100491368B1 (ko)	2005-05-24
HUP0103235A3 (en)	2003-01-28
EA002560B1 (ru)	2002-06-27
IL145959A0 (en)	2002-07-25
IL145959A (en)	2007-07-24
ATA904199A (de)	2002-05-15
PL346237A1 (en)	2002-01-28
HK1049002B (zh)	2004-12-31
GB2354239A (en)	2001-03-21
BR9917368B1 (pt)	2010-02-09
KR20020012204A (ko)	2002-02-15
SE0100193D0 (sv)	2001-01-24
GB2357761A (en)	2001-07-04
US20020077353A1 (en)	2002-06-20
JP3447267B2 (ja)	2003-09-16
GB0101504D0 (en)	2001-03-07
HUP0103235A2 (hu)	2002-01-28
UA63034C2 (en)	2004-01-15
EP1159274B1 (de)	2003-03-26
CN1140521C (zh)	2004-03-03
EP1159274A2 (de)	2001-12-05
AU2001100440A4 (en)	2001-11-01
AT4365U1 (de)	2001-06-25
PL205579B1 (pl)	2010-05-31
ITMI991581A0 (it)	1999-07-15
ATE235478T1 (de)	2003-04-15
BG106191A (en)	2002-08-30
CN1502616A (zh)	2004-06-09
CA2290127A1 (en)	2000-12-25
NO20010319D0 (no)	2001-01-19
CA2475401A1 (en)	2000-12-25
DK1159274T3 (da)	2003-07-21
ES2189699A1 (es)	2003-07-01
WO2000013648A3 (en)	2000-07-13
IS5861A (is)	2001-02-23
WO2000013648A8 (en)	2000-05-11
IS2343B (is)	2008-02-15
WO2000013648B1 (en)	2001-03-15
AR020863A1 (es)	2002-05-29
SK18402001A3 (sk)	2002-06-04
DE19983487C1 (de)	2002-07-25
MXPA01010989A (es)	2002-06-04
ES2194545T3 (es)	2003-11-16
EA200101072A1 (ru)	2002-02-28
DE69906389T2 (de)	2003-10-30
HK1049002A1 (en)	2003-04-25
CZ2001320A3 (en)	2001-05-16
CN1367786A (zh)	2002-09-04
WO2000013648A2 (en)	2000-03-16
SE0100193L (sv)	2001-04-25
NO20010319L (no)	2001-02-23
AT409961B (de)	2002-12-27
PT1159274E (pt)	2003-08-29
BR9917368A (pt)	2002-03-05
BG65574B1 (bg)	2009-01-30
TR200103702T2 (tr)	2002-06-21
FI108641B (fi)	2002-02-28
GB2357761B (en)	2001-09-05
SI1159274T1 (en)	2003-10-31
FI20010155L (fi)	2001-02-09
CA2290127C (en)	2005-01-25

Legal Events

Date	Code	Title	Description
2011-06-28	NUG	Patent has lapsed

Publication	Publication Date	Title
CA2290127C (en)	2005-01-25	Method for the preparation of citalopram
SE516689C2 (sv)	2002-02-12	Förfarande för framtällning av citalopram
NL1017414C1 (nl)	2001-03-15	Werkwijze voor de bereiding van Citalopram.
FR2805814A1 (fr)	2001-09-07	Procede de preparation du citalopram
EA005674B1 (ru)	2005-04-28	Способ получения циталопрама
US5039682A (en)	1991-08-13	6-fluoro-1,4-dihydroquinol-4-one-3-carboxylic acid derivatives and intermediates therefor
JP2003155259A (ja)	2003-05-27	芳香族アルデヒドの製造方法および新規な芳香族ジアルデヒド
US5233091A (en)	1993-08-03	6-fluoro-1,4-dihydroquinol-4-one-3-carboxylic acid derivatives and intermediates therefor
US5104868A (en)	1992-04-14	Tricyclic derivatives of 7-substituted-6-fluoro-1,4-dihydroquinol-4-one-3-carboxylic acids and esters
US5103040A (en)	1992-04-07	6-fluoro-1,4-dihydroquinol-4-one-3-carboxylic acid derivatives and intermediates therefor
JPH0665245A (ja)	1994-03-08	ピリジン−２，３−ジカルボン酸無水物の製造法
JPH09241246A (ja)	1997-09-16	ジシアノピラジン誘導体及びその製造方法
BG65271B1 (bg)	2007-11-30	Метод за получаване на циталопрам
JPS6124392B2 (de)	1986-06-10
CZ292992B6 (cs)	2004-01-14	Způsob výroby citalopramu