UA72238C2 - A method for the preparation of citalopram (variants), s-citalopram, intermediary ketones and a method for the preparation of racemic compounds - Google Patents
A method for the preparation of citalopram (variants), s-citalopram, intermediary ketones and a method for the preparation of racemic compounds Download PDFInfo
- Publication number
- UA72238C2 UA72238C2 UA2001075224A UA2001075224A UA72238C2 UA 72238 C2 UA72238 C2 UA 72238C2 UA 2001075224 A UA2001075224 A UA 2001075224A UA 2001075224 A UA2001075224 A UA 2001075224A UA 72238 C2 UA72238 C2 UA 72238C2
- Authority
- UA
- Ukraine
- Prior art keywords
- formula
- compound
- citalopram
- acyl
- dimethylamino
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 85
- 238000000034 method Methods 0.000 title claims abstract description 52
- 229960001653 citalopram Drugs 0.000 title claims abstract description 35
- 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 31
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- 150000002576 ketones Chemical class 0.000 title claims description 10
- 238000006243 chemical reaction Methods 0.000 claims abstract description 24
- 125000002252 acyl group Chemical group 0.000 claims abstract description 16
- -1 4-fluorophenylmagnesium halide Chemical class 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 claims description 8
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 claims description 8
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 8
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 8
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- 150000004820 halides Chemical class 0.000 claims description 7
- RYEXTBOQKFUPOE-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].CC[CH2-] RYEXTBOQKFUPOE-UHFFFAOYSA-M 0.000 claims description 7
- 238000007248 oxidative elimination reaction Methods 0.000 claims description 7
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 6
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- 238000006297 dehydration reaction Methods 0.000 claims description 6
- 230000003647 oxidation Effects 0.000 claims description 6
- 238000007254 oxidation reaction Methods 0.000 claims description 6
- XEEGWTLAFIZLSF-UHFFFAOYSA-N 1-oxo-3h-2-benzofuran-5-carbonitrile Chemical compound N#CC1=CC=C2C(=O)OCC2=C1 XEEGWTLAFIZLSF-UHFFFAOYSA-N 0.000 claims description 5
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- 230000003993 interaction Effects 0.000 claims description 4
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- JOWBVIAXILQDHG-UHFFFAOYSA-N 4-[(4-fluorophenyl)-hydroxymethyl]-3-(hydroxymethyl)benzonitrile Chemical compound OCC1=CC(C#N)=CC=C1C(O)C1=CC=C(F)C=C1 JOWBVIAXILQDHG-UHFFFAOYSA-N 0.000 claims description 3
- BRKADVNLTRCLOW-UHFFFAOYSA-M magnesium;fluorobenzene;bromide Chemical compound [Mg+2].[Br-].FC1=CC=[C-]C=C1 BRKADVNLTRCLOW-UHFFFAOYSA-M 0.000 claims description 3
- FTHPLWDYWAKYCY-UHFFFAOYSA-N 3,5-dimethoxybenzoyl chloride Chemical compound COC1=CC(OC)=CC(C(Cl)=O)=C1 FTHPLWDYWAKYCY-UHFFFAOYSA-N 0.000 claims description 2
- 125000003158 alcohol group Chemical group 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims 3
- MYLBTCQBKAKUTJ-UHFFFAOYSA-N 7-methyl-6,8-bis(methylsulfanyl)pyrrolo[1,2-a]pyrazine Chemical compound C1=CN=CC2=C(SC)C(C)=C(SC)N21 MYLBTCQBKAKUTJ-UHFFFAOYSA-N 0.000 claims 2
- 150000001263 acyl chlorides Chemical class 0.000 claims 1
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- 239000000543 intermediate Substances 0.000 abstract description 8
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 abstract description 3
- 239000011777 magnesium Substances 0.000 abstract description 2
- 229910052749 magnesium Inorganic materials 0.000 abstract description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
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- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
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- 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 8
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- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 7
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- 238000001816 cooling Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
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- 239000007787 solid Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 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 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-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
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 230000001430 anti-depressive effect Effects 0.000 description 3
- 229940005513 antidepressants Drugs 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
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- 239000007924 injection Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000003891 oxalate salts Chemical class 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 238000007363 ring formation reaction Methods 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
- 239000007858 starting material 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
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
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- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 2
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- 125000001072 heteroaryl group Chemical group 0.000 description 2
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
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- 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 1
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- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 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
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride 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
- 229910052682 stishovite Inorganic materials 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 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
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 229910052905 tridymite 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
- 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
- A61P25/24—Antidepressants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/56—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and doubly-bound oxygen atoms bound to the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurology (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Epidemiology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/DK1999/000581 WO2000012044A2 (en) | 1999-10-25 | 1999-10-25 | Method for the preparation of citalopram |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA72238C2 true UA72238C2 (en) | 2005-02-15 |
Family
ID=8157164
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA2001075224A UA72238C2 (en) | 1999-10-25 | 1999-10-25 | A method for the preparation of citalopram (variants), s-citalopram, intermediary ketones and a method for the preparation of racemic compounds |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US6566540B2 (xx) |
| EP (1) | EP1298124B1 (xx) |
| KR (1) | KR100505820B1 (xx) |
| AR (1) | AR024518A1 (xx) |
| AT (2) | ATE277032T1 (xx) |
| CA (1) | CA2291133C (xx) |
| CY (1) | CY1107635T1 (xx) |
| CZ (1) | CZ292894B6 (xx) |
| DE (3) | DE69935355T2 (xx) |
| DK (2) | DK1228056T3 (xx) |
| EA (1) | EA002801B1 (xx) |
| ES (1) | ES2282365T3 (xx) |
| HK (1) | HK1043129B (xx) |
| HR (1) | HRP20020344B1 (xx) |
| HU (1) | HUP0200169A3 (xx) |
| IL (3) | IL143875A0 (xx) |
| IS (1) | IS2260B (xx) |
| NO (1) | NO20071311L (xx) |
| NZ (1) | NZ512406A (xx) |
| PL (1) | PL201056B1 (xx) |
| PT (2) | PT1298124E (xx) |
| SI (2) | SI1298124T1 (xx) |
| SK (1) | SK287140B6 (xx) |
| TR (1) | TR200401456T1 (xx) |
| UA (1) | UA72238C2 (xx) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR034612A1 (es) * | 2001-06-25 | 2004-03-03 | Lundbeck & Co As H | Proceso para la preparacion del citalopram racemico y/o del s- o r-citalopram mediante la separacion de una mezcla de r- y s-citalopram |
| PE20040991A1 (es) * | 2002-08-12 | 2004-12-27 | Lundbeck & Co As H | Separacion de intermediarios para la preparacion de escitalopram |
| US20050137255A1 (en) * | 2002-12-23 | 2005-06-23 | H. Lundbeck A/S | Crystalline escitalopram hydrobromide and methods for preparing the same |
| PT1578738E (pt) * | 2002-12-23 | 2008-04-11 | Lundbeck & Co As H | Bromidrato de escitalopram e um método para a sua preparação |
| US20050154052A1 (en) * | 2003-03-24 | 2005-07-14 | Hetero Drugs Limited | Novel crystalline forms of (s)-citalopram oxalate |
| US20050196453A1 (en) * | 2004-03-05 | 2005-09-08 | H. Lundbeck A/S | Crystalline composition containing escitalopram |
| CA2626025A1 (en) * | 2005-10-14 | 2007-04-26 | Forest Laboratories, Inc. | Stable pharmaceutical formulations containing escitalopram and bupropion |
| EP1954257A4 (en) * | 2005-10-14 | 2009-05-20 | Lundbeck & Co As H | METHOD FOR TREATING DISORDERS OF THE CENTRAL NERVOUS SYSTEM WITH A LOW-DOSED COMBINATION OF ESCITALOPRAM AND BUPROPION |
| EA018064B1 (ru) * | 2007-08-03 | 2013-05-30 | Рихтер Гедеон Нирт. | Способ лечения депрессии |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1143703A (xx) | 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 |
| DE3926765A1 (de) | 1989-08-12 | 1991-02-14 | Hoechst Ag | Verfahren zur verminderung von primaerem und sekundaerem amin in einem tertiaeren amin |
| 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 |
| EA001728B1 (ru) * | 1997-07-08 | 2001-08-27 | Х.Лундбекк А/С | Способ получения циталопрама |
| UA62985C2 (en) * | 1997-11-10 | 2004-01-15 | Lunnbeck As H | A method for the preparation of citalopram |
| SK283907B6 (sk) * | 1997-11-11 | 2004-04-06 | H. Lundbeck A/S | Spôsob výroby citalopramu a medziprodukty |
| AU746665B2 (en) | 1998-10-20 | 2002-05-02 | H. Lundbeck A/S | Method for the preparation of citalopram |
| BR9916955A (pt) | 1998-12-23 | 2001-09-11 | Lundbeck & Co As H | Método para preparação de 5-cianoftalida |
| AR022329A1 (es) | 1999-01-29 | 2002-09-04 | Lundbeck & Co As H | Metodo para la preparacion de 5-cianoftalida |
| PL198024B1 (pl) | 1999-04-14 | 2008-05-30 | Lundbeck & Co As H | Sposób wytwarzania citalopramu, związki pośrednie i ich zastosowanie do wytwarzania citalopramu |
| 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 |
| 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 |
| 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 |
| GB0005477D0 (en) | 2000-03-07 | 2000-04-26 | Resolution Chemicals Limited | Process for the preparation of citalopram |
| FI20011622A (fi) | 2000-08-18 | 2002-02-19 | Lundbeck & Co As H | Menetelmä sitalopraamin valmistamiseksi |
| KR100430746B1 (ko) | 2000-12-28 | 2004-05-10 | 하. 룬트벡 아크티에 셀스카브 | 순수한 시탈로프람의 제조방법 |
-
1999
- 1999-10-25 SK SK50008-2009A patent/SK287140B6/sk not_active IP Right Cessation
- 1999-10-25 DE DE69935355T patent/DE69935355T2/de not_active Expired - Lifetime
- 1999-10-25 DE DE69920526T patent/DE69920526T2/de not_active Expired - Lifetime
- 1999-10-25 PL PL349440A patent/PL201056B1/pl not_active IP Right Cessation
- 1999-10-25 TR TR2004/01456T patent/TR200401456T1/xx unknown
- 1999-10-25 ES ES02028326T patent/ES2282365T3/es not_active Expired - Lifetime
- 1999-10-25 DK DK99950511T patent/DK1228056T3/da active
- 1999-10-25 EA EA200100593A patent/EA002801B1/ru not_active IP Right Cessation
- 1999-10-25 EP EP02028326A patent/EP1298124B1/en not_active Expired - Lifetime
- 1999-10-25 AT AT99950511T patent/ATE277032T1/de active
- 1999-10-25 PT PT02028326T patent/PT1298124E/pt unknown
- 1999-10-25 UA UA2001075224A patent/UA72238C2/uk unknown
- 1999-10-25 IL IL14387599A patent/IL143875A0/xx active IP Right Grant
- 1999-10-25 SI SI9930960T patent/SI1298124T1/sl unknown
- 1999-10-25 KR KR10-2001-7008100A patent/KR100505820B1/ko not_active IP Right Cessation
- 1999-10-25 DK DK02028326T patent/DK1298124T3/da active
- 1999-10-25 PT PT99950511T patent/PT1228056E/pt unknown
- 1999-10-25 SI SI9930703T patent/SI1228056T1/xx unknown
- 1999-10-25 AT AT02028326T patent/ATE355268T1/de active
- 1999-10-25 NZ NZ512406A patent/NZ512406A/xx not_active IP Right Cessation
- 1999-10-25 DE DE19983836A patent/DE19983836C1/de not_active Expired - Fee Related
- 1999-10-25 HU HU0200169A patent/HUP0200169A3/hu unknown
- 1999-10-25 CA CA002291133A patent/CA2291133C/en not_active Expired - Fee Related
- 1999-11-10 AR ARP990105703A patent/AR024518A1/es active IP Right Grant
-
2001
- 2001-06-15 IS IS5970A patent/IS2260B/is unknown
- 2001-06-20 IL IL143875A patent/IL143875A/en not_active IP Right Cessation
-
2002
- 2002-04-19 HR HR20020344A patent/HRP20020344B1/xx not_active IP Right Cessation
- 2002-05-03 US US10/138,811 patent/US6566540B2/en not_active Expired - Fee Related
- 2002-07-05 HK HK02105036.3A patent/HK1043129B/zh not_active IP Right Cessation
- 2002-08-29 CZ CZ20022925A patent/CZ292894B6/cs not_active IP Right Cessation
-
2006
- 2006-07-18 IL IL176943A patent/IL176943A0/en unknown
-
2007
- 2007-03-09 NO NO20071311A patent/NO20071311L/no unknown
- 2007-05-21 CY CY20071100690T patent/CY1107635T1/el unknown
Also Published As
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