SE516689C2 - Förfarande för framtällning av citalopram - Google Patents

Förfarande för framtällning av citalopram

Info

Publication number: SE516689C2
Authority: SE; Sweden
Prior art keywords: process according; formula; compound; citalopram; nickel
Prior art date: 1999-06-25

Application number

SE0100194A

Other languages

English (en)

Swedish (sv)

Other versions

SE0100194L (sv

SE0100194D0 (sv

Inventor

Hans Petersen

Michael Harold Rock

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 SE0100194D0 publication Critical patent/SE0100194D0/xx

2001-04-25 Publication of SE0100194L publication Critical patent/SE0100194L/xx

2002-02-12 Publication of SE516689C2 publication Critical patent/SE516689C2/sv

Links

238000000034 method Methods 0.000 title claims abstract description 31
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
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 21
238000006243 chemical reaction Methods 0.000 claims abstract description 12
-1 5-cyano compound Chemical class 0.000 claims abstract description 11
150000001875 compounds Chemical class 0.000 claims abstract description 9
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims abstract description 7
238000002360 preparation method Methods 0.000 claims abstract description 7
229910052801 chlorine Inorganic materials 0.000 claims abstract description 6
229910052794 bromium Inorganic materials 0.000 claims abstract description 5
150000003839 salts Chemical class 0.000 claims description 12
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical class C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 11
239000011701 zinc Substances 0.000 claims description 11
239000000460 chlorine Substances 0.000 claims description 8
MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 claims description 8
101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 claims description 6
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 6
229910052725 zinc Inorganic materials 0.000 claims description 6
230000003197 catalytic effect Effects 0.000 claims description 5
238000011065 in-situ storage Methods 0.000 claims description 5
239000003054 catalyst Substances 0.000 claims description 4
239000010949 copper Substances 0.000 claims description 4
239000003446 ligand Substances 0.000 claims description 4
VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical compound [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 0.000 claims description 3
238000007333 cyanation reaction Methods 0.000 claims description 3
229910052751 metal Inorganic materials 0.000 claims description 3
239000002184 metal Substances 0.000 claims description 3
239000002243 precursor Substances 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
229910052749 magnesium Inorganic materials 0.000 claims description 2
239000011777 magnesium Substances 0.000 claims description 2
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 2
229910052759 nickel Inorganic materials 0.000 claims description 2
101710184444 Complexin Proteins 0.000 claims 1
229910021586 Nickel(II) chloride Inorganic materials 0.000 claims 1
241001494479 Pecora Species 0.000 claims 1
QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 claims 1
238000002955 isolation Methods 0.000 abstract description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
239000002904 solvent Substances 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
239000002253 acid Substances 0.000 description 5
238000007363 ring formation reaction Methods 0.000 description 5
239000000243 solution Substances 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
239000000047 product Substances 0.000 description 4
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 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
238000003747 Grignard reaction Methods 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 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
239000007924 injection Substances 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007858 starting material Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000003826 tablet Substances 0.000 description 3
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
WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-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
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
230000000996 additive effect Effects 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
239000003795 chemical substances by application Substances 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
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000000203 mixture Substances 0.000 description 2
SFLGSKRGOWRGBR-UHFFFAOYSA-N phthalane Chemical class C1=CC=C2COCC2=C1 SFLGSKRGOWRGBR-UHFFFAOYSA-N 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
JZWFDVDETGFGFC-UHFFFAOYSA-N salacetamide Chemical group CC(=O)NC(=O)C1=CC=CC=C1O JZWFDVDETGFGFC-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-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
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
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-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
PMVSDNDAUGGCCE-TYYBGVCCSA-L Ferrous fumarate Chemical compound [Fe+2].[O-]C(=O)\C=C\C([O-])=O PMVSDNDAUGGCCE-TYYBGVCCSA-L 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
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
239000003963 antioxidant agent Substances 0.000 description 1
229960001230 asparagine Drugs 0.000 description 1
235000009582 asparagine Nutrition 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
239000012267 brine Substances 0.000 description 1
125000001246 bromo group Chemical group Br* 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
235000017803 cinnamon Nutrition 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000008120 corn starch 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
238000011049 filling Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
239000012458 free base 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
LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
150000002500 ions 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
239000012299 nitrogen atmosphere Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000006408 oxalic acid Nutrition 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
229920001592 potato starch Polymers 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
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 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
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
235000021419 vinegar Nutrition 0.000 description 1
239000000052 vinegar Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2282—Unsaturated compounds used as ligands
- B01J31/2295—Cyclic compounds, e.g. cyclopentadienyls
- 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
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
- 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
- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
- B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
- B01J2231/4205—C-C cross-coupling, e.g. metal catalyzed or Friedel-Crafts type
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/84—Metals of the iron group
- B01J2531/847—Nickel

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Inorganic Chemistry (AREA)
Materials Engineering (AREA)
Neurology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Bioinformatics & Cheminformatics (AREA)
Epidemiology (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Hospice & Palliative Care (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)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Steroid Compounds (AREA)
Furan Compounds (AREA)

SE0100194A 1999-06-25 2001-01-24 Förfarande för framtällning av citalopram SE516689C2 (sv)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DKPA199900921		1999-06-25
PCT/DK1999/000643 WO2000011926A2 (en)	1999-06-25	1999-11-19	Method for the preparation of citalopram

Publications (3)

Publication Number	Publication Date
SE0100194D0 SE0100194D0 (sv)	2001-01-24
SE0100194L SE0100194L (sv)	2001-04-25
SE516689C2 true SE516689C2 (sv)	2002-02-12

Family

ID=8099044

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE0100194A SE516689C2 (sv)	1999-06-25	2001-01-24	Förfarande för framtällning av citalopram

Country Status (36)

Country	Link
US (1)	US6750358B2 (de)
EP (1)	EP1105382B1 (de)
JP (1)	JP3389571B2 (de)
KR (1)	KR100491369B1 (de)
CN (1)	CN1129593C (de)
AR (1)	AR020573A1 (de)
AT (3)	ATE213237T1 (de)
AU (2)	AU1374800A (de)
BG (1)	BG106190A (de)
BR (1)	BR9917367A (de)
CA (1)	CA2290125C (de)
CH (1)	CH691304A5 (de)
CZ (1)	CZ292174B6 (de)
DE (2)	DE69900891D1 (de)
DK (1)	DK1105382T3 (de)
EA (1)	EA002661B1 (de)
ES (1)	ES2172356T3 (de)
FI (1)	FI108538B (de)
GB (1)	GB2354240B (de)
HK (1)	HK1047745B (de)
HU (1)	HUP0103417A3 (de)
IL (1)	IL145960A0 (de)
IS (1)	IS5862A (de)
IT (1)	ITMI991579A1 (de)
MX (1)	MXPA01010986A (de)
NO (1)	NO20010318L (de)
NZ (1)	NZ514982A (de)
PL (1)	PL345971A1 (de)
PT (1)	PT1105382E (de)
SE (1)	SE516689C2 (de)
SI (1)	SI1105382T1 (de)
SK (1)	SK18412001A3 (de)
TR (1)	TR200103700T2 (de)
UA (1)	UA62023C2 (de)
WO (1)	WO2000011926A2 (de)
ZA (1)	ZA200108855B (de)

Families Citing this family (40)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SI1140886T1 (en)	1998-12-23	2003-08-31	H. Lundbeck A/S	Method for the preparation of 5-cyanophthalide
AR022329A1 (es)	1999-01-29	2002-09-04	Lundbeck & Co As H	Metodo para la preparacion de 5-cianoftalida
TR200102957T2 (tr)	1999-04-14	2004-12-21	H. Lundbeck A/S	Sitalopram hazırlanması için metod.
ITMI991579A1 (it)	1999-06-25	2001-01-15	Lundbeck & Co As H	Metodo per la preparazione di citalopram
ITMI991581A1 (it) *	1999-06-25	2001-01-15	Lundbeck & Co As H	Metodo per la preparazione di citalopram
HRP20020344B1 (hr)	1999-10-25	2010-10-31	H. Lundbeck A/S	Način priprave citaloprama
EP1228056B1 (de)	1999-10-25	2004-09-22	H. Lundbeck A/S	Verfahren zur herstellung von citalopram
AR026063A1 (es)	1999-11-01	2002-12-26	Lundbeck & Co As H	Metodo para la preparacion de 5-carboxiftalida.
EP1246812B1 (de)	1999-12-28	2004-03-17	H. Lundbeck A/S	Verfahren zur herstellung von citalopram
SI1246813T1 (en)	1999-12-30	2004-08-31	H. Lundbeck A/S	Method for the preparation of citalopram
PL197821B1 (pl)	2000-01-14	2008-04-30	Lundbeck & Co As H	Sposób wytwarzania 5-cyjanoftalidu
FR2805812A1 (fr)	2000-02-24	2001-09-07	Lundbeck & Co As H	Procede de preparation du citalopram
NL1017417C1 (nl)	2000-03-03	2001-03-16	Lundbeck & Co As H	Werkwijze voor de bereiding van Citalopram.
GB0005477D0 (en)	2000-03-07	2000-04-26	Resolution Chemicals Limited	Process for the preparation of citalopram
NL1017500C1 (nl)	2000-03-13	2001-04-26	Lundbeck & Co As H	Werkwijze voor de bereiding van Citalopram.
GB2357762B (en) *	2000-03-13	2002-01-30	Lundbeck & Co As H	Crystalline base of citalopram
PL360110A1 (en)	2000-03-13	2004-09-06	H.Lundbeck A/S	Method for the preparation of citalopram
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
JP2003527386A (ja)	2000-03-14	2003-09-16	ハー・ルンドベック・アクチエゼルスカベット	シタロプラムの製造方法
CH692148A5 (de) *	2000-03-16	2002-02-28	Lundbeck & Co As H	Verfahren zur Herstellung von Citalopram.
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
IL148525A0 (en) *	2000-07-06	2002-09-12	Lundbeck & Co As H	Method for the preparation of citalopram
CA2354877C (en)	2000-08-18	2006-05-02	H. Lundbeck A/S	Method for the preparation of citalopram
EA003581B1 (ru)	2000-12-22	2003-06-26	Х.Лундбекк А/С	Способ получения чистого циталопрама
AU2001100399B4 (en) *	2000-12-28	2002-03-21	H Lundbeck As	Process for the preparation of pure citalopram
WO2002060886A1 (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
CZ20032567A3 (en) *	2001-03-09	2004-04-14	Ranbaxy Laboratories Limited	Process for the preparation of citalopram
EA006213B1 (ru) *	2001-07-31	2005-10-27	Х. Лундбекк А/С	Кристаллическая композиция, содержащая эсциталопрам
AU2003222435A1 (en)	2002-01-07	2003-07-24	Sun Pharmaceutical Industries Limited	Process for the preparation of 1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)- 1,3-dihydro-5-isobenzofuran carbonitrile
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
WO2004085416A1 (en) *	2003-03-24	2004-10-07	Hetero Drugs Limited	Novel crystalline forms of (s)-citalopram oxalate
US7019153B2 (en)	2003-06-10	2006-03-28	Sun Pharmaceutical Industries Limited	Process for hydrogenolysis of [1-(3-dimethylamino)propyl)]-1-(4-fluorophenyl)-1,3-dihydro-5-halo-isobenzofuran acetamido-3-substituted-3-cephem-4-carboxylic acid
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
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
WO2006021971A2 (en)	2004-08-23	2006-03-02	Sun Pharmaceutical Industries Limited	'process for preparation of citalopram and enantiomers'
WO2006103550A1 (en) *	2005-03-31	2006-10-05	Ranbaxy Laboratories Limited	Processes for the preparation of citalopram and its intermediate 5-aminophthalide
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
EP2017271A1 (de)	2007-07-06	2009-01-21	Aurobindo Pharma Limited	Verfahren zur Herstellung von Escitalopram

Family Cites Families (24)

* 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
CA2010159A1 (en)	1989-02-21	1990-08-21	James J. Maul	Cyanation of haloaromatics utilizing catalysts generated in situ starting with nic1 or nic1 6h 0
US5296507A (en)	1990-09-06	1994-03-22	H.Lundbeck A/S	Treatment of cerbrovascular 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
DE19706648A1 (de)	1997-02-20	1998-08-27	Bayer Ag	Verfahren zur Herstellung von aromatischen Nitrilen
CN1206207C (zh)	1997-07-08	2005-06-15	H.隆德贝克有限公司	氰酞氟苯胺的制备方法
UA62985C2 (en)	1997-11-10	2004-01-15	Lunnbeck As H	A method for the preparation of citalopram
HUP0002953A3 (en)	1997-11-11	2002-12-28	Lundbeck & Co As H	Method for preparation of citalopram and intermediates used for them
DE69904853T2 (de)	1998-10-20	2003-09-04	Lundbeck As Valby H	Verfahren zur herstellung von citalopram
SI1140886T1 (en)	1998-12-23	2003-08-31	H. Lundbeck A/S	Method for the preparation of 5-cyanophthalide
AR022329A1 (es)	1999-01-29	2002-09-04	Lundbeck & Co As H	Metodo para la preparacion de 5-cianoftalida
DE10015280A1 (de)	1999-03-29	2001-01-04	Nissan Chemical Ind Ltd	Verfahren zur Herstellung von Benzonitrilverbindungen
TR200102957T2 (tr)	1999-04-14	2004-12-21	H. Lundbeck A/S	Sitalopram hazırlanması için metod.
ITMI991579A1 (it)	1999-06-25	2001-01-15	Lundbeck & Co As H	Metodo per la preparazione di citalopram
ITMI991581A1 (it)	1999-06-25	2001-01-15	Lundbeck & Co As H	Metodo per la preparazione di citalopram
EP1228056B1 (de)	1999-10-25	2004-09-22	H. Lundbeck A/S	Verfahren zur herstellung von citalopram
US6310222B1 (en)	1999-11-01	2001-10-30	Sumika Fine Chemicals Co., Ltd.	Production method of 5-phthalancarbonitrile compound, intermediate therefor and production method of the intermediate
GB0005477D0 (en)	2000-03-07	2000-04-26	Resolution Chemicals Limited	Process for the preparation of citalopram
EA003581B1 (ru)	2000-12-22	2003-06-26	Х.Лундбекк А/С	Способ получения чистого циталопрама
AU2001100399B4 (en)	2000-12-28	2002-03-21	H Lundbeck As	Process for the preparation of pure citalopram

1999
- 1999-07-15 IT IT1999MI001579A patent/ITMI991579A1/it unknown
- 1999-11-19 SI SI9930039T patent/SI1105382T1/xx unknown
- 1999-11-19 MX MXPA01010986A patent/MXPA01010986A/es not_active IP Right Cessation
- 1999-11-19 CN CN99816768A patent/CN1129593C/zh not_active Expired - Fee Related
- 1999-11-19 WO PCT/DK1999/000643 patent/WO2000011926A2/en not_active Ceased
- 1999-11-19 AT AT99968206T patent/ATE213237T1/de not_active IP Right Cessation
- 1999-11-19 AT AT0904099A patent/AT409960B/de not_active IP Right Cessation
- 1999-11-19 GB GB0101508A patent/GB2354240B/en not_active Expired - Fee Related
- 1999-11-19 HU HU0103417A patent/HUP0103417A3/hu unknown
- 1999-11-19 CH CH00307/01A patent/CH691304A5/de not_active IP Right Cessation
- 1999-11-19 AU AU13748/00A patent/AU1374800A/en active Pending
- 1999-11-19 ES ES99968206T patent/ES2172356T3/es not_active Expired - Lifetime
- 1999-11-19 KR KR10-2001-7013971A patent/KR100491369B1/ko not_active Expired - Fee Related
- 1999-11-19 PL PL99345971A patent/PL345971A1/xx not_active Application Discontinuation
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- 1999-11-19 UA UA2001117897A patent/UA62023C2/uk unknown
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- 1999-11-19 BR BR9917367-0A patent/BR9917367A/pt not_active IP Right Cessation
- 1999-11-19 SK SK1841-2001A patent/SK18412001A3/sk unknown
- 1999-11-19 DE DE69900891T patent/DE69900891D1/de not_active Expired - Lifetime
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- 1999-11-19 EP EP99968206A patent/EP1105382B1/de not_active Expired - Lifetime
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- 1999-11-19 AU AU2001100433A patent/AU2001100433B4/en not_active Ceased
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- 1999-11-22 CA CA002290125A patent/CA2290125C/en not_active Expired - Fee Related
2000
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2001
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- 2001-10-26 ZA ZA200108855A patent/ZA200108855B/xx unknown
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Also Published As

Publication number	Publication date
DE19983486C2 (de)	2002-09-05
CN1356993A (zh)	2002-07-03
AT409960B (de)	2002-12-27
JP2002523432A (ja)	2002-07-30
AU2001100433B4 (en)	2002-01-17
ITMI991579A1 (it)	2001-01-15
HUP0103417A2 (hu)	2002-01-28
KR100491369B1 (ko)	2005-05-24
FI20010154L (fi)	2001-02-09
CH691304A5 (de)	2001-06-29
IS5862A (is)	2001-02-23
NZ514982A (en)	2004-01-30
WO2000011926A2 (en)	2000-03-09
DE69900891D1 (de)	2002-03-21
ITMI991579A0 (it)	1999-07-15
GB2354240A (en)	2001-03-21
SE0100194L (sv)	2001-04-25
EA200101071A1 (ru)	2002-02-28
CA2290125A1 (en)	2000-12-25
SK18412001A3 (sk)	2002-05-09
HUP0103417A3 (en)	2003-01-28
ATE213237T1 (de)	2002-02-15
SE0100194D0 (sv)	2001-01-24
FI108538B (fi)	2002-02-15
CA2290125C (en)	2004-08-10
WO2000011926A3 (en)	2000-06-29
AU2001100433A4 (en)	2001-11-01
PL345971A1 (en)	2002-01-14
BR9917367A (pt)	2002-03-05
HK1047745A1 (en)	2003-03-07
HK1047745B (zh)	2004-09-10
ZA200108855B (en)	2002-08-28
US6750358B2 (en)	2004-06-15
IL145960A0 (en)	2002-07-25
AR020573A1 (es)	2002-05-15
CZ2001319A3 (en)	2001-05-16
SI1105382T1 (en)	2002-06-30
JP3389571B2 (ja)	2003-03-24
MXPA01010986A (es)	2002-06-04
NO20010318D0 (no)	2001-01-19
DE19983486T1 (de)	2001-10-18
BG106190A (en)	2002-08-30
DK1105382T3 (da)	2002-05-27
PT1105382E (pt)	2002-07-31
ES2172356T3 (es)	2002-09-16
AU1374800A (en)	2000-03-21
UA62023C2 (en)	2003-12-15
GB0101508D0 (en)	2001-03-07
NO20010318L (no)	2001-02-20
US20020061925A1 (en)	2002-05-23
ATA904099A (de)	2002-05-15
EP1105382B1 (de)	2002-02-13
EA002661B1 (ru)	2002-08-29
CN1129593C (zh)	2003-12-03
TR200103700T2 (tr)	2002-05-21
AT4366U1 (de)	2001-06-25
EP1105382A2 (de)	2001-06-13
GB2354240B (en)	2001-05-23
KR20020011982A (ko)	2002-02-09
CZ292174B6 (cs)	2003-08-13

Legal Events

Date	Code	Title	Description
2006-07-25	NUG	Patent has lapsed

Publication	Publication Date	Title
SE516689C2 (sv)	2002-02-12	Förfarande för framtällning av citalopram
SE516690C2 (sv)	2002-02-12	Förfarande för framställning av citalopram
DE60106932T2 (de)	2005-11-03	Verfahren zur herstellung von citalopram
JP3798982B2 (ja)	2006-07-19	純粋なシタロプラムの製造方法
SE517136C2 (sv)	2002-04-16	Kristallin bas av citalopram
DE60133280T2 (de)	2009-04-16	Verfahren zur herstellung von citalopram
KR100821912B1 (ko)	2008-04-16	시탈로프람의 제조 방법
BG104487A (bg)	2001-01-31	Метод за получаване на циталопрам