NO328359B1 - Fremgangsmate for fremstilling av 5-cyanoftalid - Google Patents
Fremgangsmate for fremstilling av 5-cyanoftalid Download PDFInfo
- Publication number
- NO328359B1 NO328359B1 NO20023150A NO20023150A NO328359B1 NO 328359 B1 NO328359 B1 NO 328359B1 NO 20023150 A NO20023150 A NO 20023150A NO 20023150 A NO20023150 A NO 20023150A NO 328359 B1 NO328359 B1 NO 328359B1
- Authority
- NO
- Norway
- Prior art keywords
- isobenzofuran
- nacn
- catalyst
- pph3
- reaction
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title abstract description 7
- XEEGWTLAFIZLSF-UHFFFAOYSA-N 1-oxo-3h-2-benzofuran-5-carbonitrile Chemical compound N#CC1=CC=C2C(=O)OCC2=C1 XEEGWTLAFIZLSF-UHFFFAOYSA-N 0.000 title description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 239000003054 catalyst Substances 0.000 claims description 14
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 claims description 10
- 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 10
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 8
- NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [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 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 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- CQAKANQMFXBJJQ-UHFFFAOYSA-N 5-iodo-3h-2-benzofuran-1-one Chemical compound IC1=CC=C2C(=O)OCC2=C1 CQAKANQMFXBJJQ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 238000011065 in-situ storage Methods 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- UBRQBEBBOSKYLQ-UHFFFAOYSA-N 5-chloro-3h-2-benzofuran-1-one Chemical compound ClC1=CC=C2C(=O)OCC2=C1 UBRQBEBBOSKYLQ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 239000002608 ionic liquid Substances 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 claims 3
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 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 abstract description 12
- 229960001653 citalopram Drugs 0.000 abstract description 12
- 239000000935 antidepressant agent Substances 0.000 abstract description 5
- 230000001430 anti-depressive effect Effects 0.000 abstract description 4
- 229940005513 antidepressants Drugs 0.000 abstract description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 239000011701 zinc Substances 0.000 description 9
- 239000000543 intermediate Substances 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- 125000004093 cyano group Chemical group *C#N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 239000000538 analytical sample Substances 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 4
- IUSPXLCLQIZFHL-UHFFFAOYSA-N 5-bromo-3h-2-benzofuran-1-one Chemical compound BrC1=CC=C2C(=O)OCC2=C1 IUSPXLCLQIZFHL-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 239000012300 argon atmosphere Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000005587 bubbling Effects 0.000 description 3
- 244000309464 bull Species 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- -1 4-fluorophenylmagnesium halide Chemical class 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 150000002825 nitriles Chemical group 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- ANYWGXDASKQYAD-UHFFFAOYSA-N 5-nitroisoindole-1,3-dione Chemical compound [O-][N+](=O)C1=CC=C2C(=O)NC(=O)C2=C1 ANYWGXDASKQYAD-UHFFFAOYSA-N 0.000 description 1
- 206010012289 Dementia Diseases 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical compound [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000276498 Pollachius virens Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 101150085323 in gene Proteins 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- WXHIJDCHNDBCNY-UHFFFAOYSA-N palladium dihydride Chemical compound [PdH2] WXHIJDCHNDBCNY-UHFFFAOYSA-N 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
- C07D307/88—Benzo [c] furans; Hydrogenated benzo [c] furans with one oxygen atom directly attached in position 1 or 3
-
- 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
-
- 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
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/74—Iron group metals
- B01J23/755—Nickel
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Steroid Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Cephalosporin Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/DK1999/000740 WO2001049672A1 (fr) | 1999-12-30 | 1999-12-30 | Procede de preparation de citaloprame |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20023150L NO20023150L (no) | 2002-06-28 |
| NO20023150D0 NO20023150D0 (no) | 2002-06-28 |
| NO328359B1 true NO328359B1 (no) | 2010-02-01 |
Family
ID=8157174
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20023150A NO328359B1 (no) | 1999-12-30 | 2002-06-28 | Fremgangsmate for fremstilling av 5-cyanoftalid |
Country Status (28)
| Country | Link |
|---|---|
| US (2) | US20020198391A1 (fr) |
| EP (1) | EP1246813B1 (fr) |
| JP (1) | JP2003519218A (fr) |
| KR (1) | KR100653141B1 (fr) |
| CN (1) | CN1211377C (fr) |
| AT (1) | ATE253568T1 (fr) |
| AU (1) | AU1858400A (fr) |
| BR (1) | BR9917604A (fr) |
| CA (1) | CA2395733C (fr) |
| CZ (1) | CZ20022627A3 (fr) |
| DE (1) | DE69912652T2 (fr) |
| DK (1) | DK1246813T3 (fr) |
| EA (1) | EA004055B1 (fr) |
| ES (1) | ES2207312T3 (fr) |
| HK (1) | HK1052512B (fr) |
| HR (1) | HRP20020633A2 (fr) |
| HU (1) | HUP0203840A3 (fr) |
| IL (2) | IL150367A0 (fr) |
| IS (1) | IS2167B (fr) |
| MX (1) | MXPA02006504A (fr) |
| NO (1) | NO328359B1 (fr) |
| PL (1) | PL198803B1 (fr) |
| PT (1) | PT1246813E (fr) |
| SI (1) | SI1246813T1 (fr) |
| SK (1) | SK11052002A3 (fr) |
| TR (1) | TR200201688T2 (fr) |
| UA (1) | UA73336C2 (fr) |
| WO (1) | WO2001049672A1 (fr) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE237604T1 (de) | 1999-04-14 | 2003-05-15 | Lundbeck & Co As H | Verfahren zur herstellung von citalopram |
| SI1246812T1 (en) | 1999-12-28 | 2004-08-31 | H. Lundbeck A/S | Method for the preparation of citalopram |
| IL150561A0 (en) | 2000-01-14 | 2003-02-12 | Lundbeck & Co As H | Method for the preparation of 5-cyanophthalide |
| IES20010157A2 (en) | 2000-03-03 | 2002-03-06 | 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 |
| CN1429219A (zh) | 2000-03-13 | 2003-07-09 | H·隆德贝克有限公司 | 制备西酞普兰的方法 |
| IES20010206A2 (en) | 2000-03-13 | 2002-03-06 | Lundbeck & Co As H | Method for the preparation of citalopram |
| CA2402553A1 (fr) | 2000-03-13 | 2001-09-20 | H. Lundbeck A/S | Alkylation progressive de 1-(4-fluorophenyl)-1,3-dihydroisobenzofuranes 5-substitues |
| ATE257832T1 (de) | 2000-03-14 | 2004-01-15 | 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 |
| US6339182B1 (en) * | 2000-06-20 | 2002-01-15 | Chevron U.S.A. Inc. | Separation of olefins from paraffins using ionic liquid solutions |
| US20050154052A1 (en) * | 2003-03-24 | 2005-07-14 | Hetero Drugs Limited | Novel crystalline forms of (s)-citalopram oxalate |
| CN100457747C (zh) * | 2006-11-21 | 2009-02-04 | 浙江大学 | 抗抑郁药西酞普兰关键中间体5-氰基苯酞的制备工艺 |
| CN103127815B (zh) * | 2013-02-19 | 2015-10-28 | 浙江大学 | 一种利用卤硫作用提高二氧化硫捕集性能的方法 |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1143703A (fr) | 1965-03-18 | |||
| GB1526331A (en) * | 1976-01-14 | 1978-09-27 | Kefalas As | Phthalanes |
| US4665181A (en) * | 1984-05-17 | 1987-05-12 | Pennwalt Corporation | Anti-inflammatory phthalazinones |
| GB8419963D0 (en) * | 1984-08-06 | 1984-09-12 | Lundbeck & Co As H | Intermediate compound and method |
| US5296507A (en) | 1990-09-06 | 1994-03-22 | H.Lundbeck A/S | Treatment of cerbrovascular disorders |
| JPH0881456A (ja) * | 1994-09-14 | 1996-03-26 | Sumitomo Chem Co Ltd | １，１，３，３−テトラクロロ−１，３−ジヒドロイソベンゾフラン誘導体の製造法 |
| 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 |
| DK1015416T3 (da) * | 1997-07-08 | 2001-11-05 | Lundbeck & Co As H | Fremgangsmåde til fremstilling af citalopram |
| UA62985C2 (en) | 1997-11-10 | 2004-01-15 | Lunnbeck As H | A method for the preparation of citalopram |
| EA002770B1 (ru) | 1997-11-11 | 2002-08-29 | Х.Лундбекк А/С | Способ получения циталопрама |
| KR100411505B1 (ko) | 1998-10-20 | 2003-12-18 | 하. 룬트벡 아크티에 셀스카브 | 시탈로프람의 제조방법 |
| CA2356188C (fr) | 1998-12-23 | 2006-05-23 | H. Lundbeck A/S | Technique de preparation de 5-cyanophtalide |
| AR022329A1 (es) | 1999-01-29 | 2002-09-04 | Lundbeck & Co As H | Metodo para la preparacion de 5-cianoftalida |
| ATE237604T1 (de) | 1999-04-14 | 2003-05-15 | Lundbeck & Co As H | Verfahren zur herstellung von citalopram |
| 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 |
| ES2229774T3 (es) | 1999-10-25 | 2005-04-16 | H. Lundbeck A/S | Metodo para la preparacion de citalopram. |
| AR026063A1 (es) | 1999-11-01 | 2002-12-26 | Lundbeck & Co As H | Metodo para la preparacion de 5-carboxiftalida. |
| 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 |
| SI1246812T1 (en) | 1999-12-28 | 2004-08-31 | H. Lundbeck A/S | Method for the preparation of citalopram |
| IL150561A0 (en) | 2000-01-14 | 2003-02-12 | Lundbeck & Co As H | Method for the preparation of 5-cyanophthalide |
| IES20010143A2 (en) | 2000-02-24 | 2001-07-25 | Lundbeck & Co As H | Method for the preparation of citalopram |
| NL1017415C1 (nl) | 2000-02-24 | 2001-05-18 | 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 |
| FI20011621A (fi) | 2000-08-18 | 2002-02-19 | Lundbeck & Co As H | Menetelmä sitalopraamin valmistamiseksi |
| EA003581B1 (ru) | 2000-12-22 | 2003-06-26 | Х.Лундбекк А/С | Способ получения чистого циталопрама |
| EA003459B1 (ru) | 2000-12-28 | 2003-06-26 | Х.Лундбекк А/С | Способ получения чистого циталопрама |
-
1999
- 1999-12-30 HU HU0203840A patent/HUP0203840A3/hu unknown
- 1999-12-30 TR TR2002/01688T patent/TR200201688T2/xx unknown
- 1999-12-30 EP EP99962133A patent/EP1246813B1/fr not_active Expired - Lifetime
- 1999-12-30 CN CNB998170674A patent/CN1211377C/zh not_active Expired - Fee Related
- 1999-12-30 SK SK1105-2002A patent/SK11052002A3/sk unknown
- 1999-12-30 ES ES99962133T patent/ES2207312T3/es not_active Expired - Lifetime
- 1999-12-30 BR BR9917604-1A patent/BR9917604A/pt not_active Application Discontinuation
- 1999-12-30 AT AT99962133T patent/ATE253568T1/de not_active IP Right Cessation
- 1999-12-30 JP JP2001550212A patent/JP2003519218A/ja active Pending
- 1999-12-30 WO PCT/DK1999/000740 patent/WO2001049672A1/fr active IP Right Grant
- 1999-12-30 MX MXPA02006504A patent/MXPA02006504A/es active IP Right Grant
- 1999-12-30 SI SI9930473T patent/SI1246813T1/xx unknown
- 1999-12-30 CA CA002395733A patent/CA2395733C/fr not_active Expired - Fee Related
- 1999-12-30 KR KR1020027008572A patent/KR100653141B1/ko not_active IP Right Cessation
- 1999-12-30 AU AU18584/00A patent/AU1858400A/en not_active Abandoned
- 1999-12-30 DE DE69912652T patent/DE69912652T2/de not_active Expired - Lifetime
- 1999-12-30 PT PT99962133T patent/PT1246813E/pt unknown
- 1999-12-30 IL IL15036799A patent/IL150367A0/xx unknown
- 1999-12-30 DK DK99962133T patent/DK1246813T3/da active
- 1999-12-30 PL PL355531A patent/PL198803B1/pl not_active IP Right Cessation
- 1999-12-30 UA UA2002065265A patent/UA73336C2/uk unknown
- 1999-12-30 EA EA200200728A patent/EA004055B1/ru not_active IP Right Cessation
- 1999-12-30 CZ CZ20022627A patent/CZ20022627A3/cs unknown
-
2002
- 2002-06-19 IS IS6433A patent/IS2167B/is unknown
- 2002-06-23 IL IL150367A patent/IL150367A/en not_active IP Right Cessation
- 2002-06-27 US US10/186,337 patent/US20020198391A1/en not_active Abandoned
- 2002-06-28 NO NO20023150A patent/NO328359B1/no not_active IP Right Cessation
- 2002-07-26 HR HRP20020633 patent/HRP20020633A2/hr not_active Application Discontinuation
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2003
- 2003-07-08 HK HK03104874.0A patent/HK1052512B/zh not_active IP Right Cessation
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2005
- 2005-11-23 US US11/285,922 patent/US7271273B2/en not_active Expired - Fee Related
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