UA72039C2 - A method for the preparation of citalopram - Google Patents
A method for the preparation of citalopram Download PDFInfo
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- UA72039C2 UA72039C2 UA2002118821A UA2002118821A UA72039C2 UA 72039 C2 UA72039 C2 UA 72039C2 UA 2002118821 A UA2002118821 A UA 2002118821A UA 2002118821 A UA2002118821 A UA 2002118821A UA 72039 C2 UA72039 C2 UA 72039C2
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- Ukraine
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- formula
- compound
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- intermediate compound
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- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 38
- 229960001653 citalopram Drugs 0.000 title claims abstract description 26
- 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 25
- 238000002360 preparation method Methods 0.000 title abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 83
- 239000007800 oxidant agent Substances 0.000 claims abstract description 3
- 230000003993 interaction Effects 0.000 claims description 22
- 238000005804 alkylation reaction Methods 0.000 claims description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- 230000029936 alkylation Effects 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 16
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 15
- 238000007363 ring formation reaction Methods 0.000 claims description 13
- -1 benzyl halide Chemical class 0.000 claims description 12
- 239000003638 chemical reducing agent Substances 0.000 claims description 12
- 230000015572 biosynthetic process Effects 0.000 claims description 9
- 239000012024 dehydrating agents Substances 0.000 claims description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- 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 description 4
- 238000007098 aminolysis reaction Methods 0.000 claims description 4
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 claims description 4
- 230000003213 activating effect Effects 0.000 claims 2
- 101800001775 Nuclear inclusion protein A Proteins 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 22
- 239000000203 mixture Substances 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 229910021529 ammonia Inorganic materials 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical group [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 6
- 239000000654 additive Substances 0.000 description 5
- 239000000935 antidepressant agent Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical group 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- IGEKIFWYHHOBIB-UHFFFAOYSA-N 1-(4-fluorophenyl)-3-oxo-1h-2-benzofuran-5-carboxylic acid Chemical compound O1C(=O)C2=CC(C(=O)O)=CC=C2C1C1=CC=C(F)C=C1 IGEKIFWYHHOBIB-UHFFFAOYSA-N 0.000 description 3
- ADGFGICBGFREFM-UHFFFAOYSA-N 3-[5-(aminomethyl)-1-(4-fluorophenyl)-3h-2-benzofuran-1-yl]-n,n-dimethylpropan-1-amine Chemical compound O1CC2=CC(CN)=CC=C2C1(CCCN(C)C)C1=CC=C(F)C=C1 ADGFGICBGFREFM-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- 238000003747 Grignard reaction Methods 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000004480 active ingredient 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
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 239000012485 toluene extract Substances 0.000 description 3
- 230000009466 transformation Effects 0.000 description 3
- OWQCIMGISJMQQQ-UHFFFAOYSA-N 5-(bromomethyl)-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran Chemical compound C1=CC(F)=CC=C1C1C2=CC=C(CBr)C=C2CO1 OWQCIMGISJMQQQ-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000001540 azides Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 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
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 239000010502 orange oil Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 2
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- YXCRMKYHFFMNPT-UHFFFAOYSA-N 1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile Chemical compound C1=CC(F)=CC=C1C1C2=CC=C(C#N)C=C2CO1 YXCRMKYHFFMNPT-UHFFFAOYSA-N 0.000 description 1
- VVXGNGGTQDOLGK-UHFFFAOYSA-N 1-(4-fluorophenyl)-3-oxo-1h-2-benzofuran-5-carbonitrile Chemical compound C1=CC(F)=CC=C1C1C2=CC=C(C#N)C=C2C(=O)O1 VVXGNGGTQDOLGK-UHFFFAOYSA-N 0.000 description 1
- TVZPFXMISWZNCC-UHFFFAOYSA-N 1-(4-fluorophenyl)-3-oxo-1h-2-benzofuran-5-carboxamide Chemical compound O1C(=O)C2=CC(C(=O)N)=CC=C2C1C1=CC=C(F)C=C1 TVZPFXMISWZNCC-UHFFFAOYSA-N 0.000 description 1
- 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
- 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 1
- JTNCEQNHURODLX-UHFFFAOYSA-N 2-phenylethanimidamide Chemical compound NC(=N)CC1=CC=CC=C1 JTNCEQNHURODLX-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
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- 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
- 239000000377 silicon dioxide Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 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
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-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
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA200000783 | 2000-05-12 | ||
| PCT/DK2001/000333 WO2001085712A1 (en) | 2000-05-12 | 2001-05-10 | Method for the preparation of citalopram |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA72039C2 true UA72039C2 (en) | 2005-01-17 |
Family
ID=8159493
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA2002118821A UA72039C2 (en) | 2000-05-12 | 2001-10-05 | A method for the preparation of citalopram |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US6660873B2 (de) |
| EP (1) | EP1296970B1 (de) |
| JP (1) | JP2003532721A (de) |
| CN (1) | CN100422166C (de) |
| AR (1) | AR032455A1 (de) |
| AT (1) | ATE389645T1 (de) |
| AU (2) | AU5823901A (de) |
| BG (1) | BG65820B1 (de) |
| BR (1) | BR0110996A (de) |
| CA (1) | CA2408292C (de) |
| CZ (1) | CZ20024065A3 (de) |
| DE (1) | DE60133280T2 (de) |
| DK (1) | DK1296970T3 (de) |
| EA (1) | EA005674B1 (de) |
| ES (1) | ES2301541T3 (de) |
| HK (1) | HK1056171A1 (de) |
| HR (1) | HRP20020881A2 (de) |
| HU (1) | HUP0301942A2 (de) |
| IL (2) | IL152645A0 (de) |
| IS (1) | IS2586B (de) |
| MX (1) | MXPA02011125A (de) |
| NO (1) | NO327963B1 (de) |
| NZ (1) | NZ522475A (de) |
| PL (1) | PL358144A1 (de) |
| PT (1) | PT1296970E (de) |
| SI (1) | SI1296970T1 (de) |
| SK (1) | SK287035B6 (de) |
| UA (1) | UA72039C2 (de) |
| WO (1) | WO2001085712A1 (de) |
| ZA (1) | ZA200208973B (de) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2195554T5 (es) | 1999-04-14 | 2010-02-02 | H. Lundbeck A/S | Metodo para la preparacion de 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 |
| US6433196B1 (en) * | 2000-02-17 | 2002-08-13 | Sumika Fine Chemicals Co., Ltd. | Production method of citalopram, intermediate therefor and production method of the intermediate |
| NL1017417C1 (nl) | 2000-03-03 | 2001-03-16 | Lundbeck & Co As H | Werkwijze voor de bereiding van Citalopram. |
| NL1017500C1 (nl) | 2000-03-13 | 2001-04-26 | Lundbeck & Co As H | Werkwijze voor de bereiding van Citalopram. |
| PL357022A1 (en) | 2000-03-13 | 2004-07-12 | H.Lundbeck A/S | Stepwise alkylation of 5-substituted 1-(4-fluorophenyl)-1,3-dihydroisobenzofurans |
| 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 |
| IN192057B (de) * | 2001-07-19 | 2004-02-14 | Ranbaxy Lab Ltd | |
| WO2004085416A1 (en) * | 2003-03-24 | 2004-10-07 | Hetero Drugs Limited | Novel crystalline forms of (s)-citalopram oxalate |
| AU2003278409A1 (en) * | 2003-10-28 | 2005-05-19 | Krishnaji Upadhye Bhargav | Improved process for the manufacture of citalopram hydrobromide |
| US20050143350A1 (en) * | 2003-11-19 | 2005-06-30 | Seed John C. | Combination drug therapy to treat obesity |
| KR101166280B1 (ko) | 2004-08-23 | 2013-11-27 | 썬 파마 글로벌 에프제트이 | 시탈로프램 및 에난티오머의 제조 방법 |
Family Cites Families (40)
| 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 |
| 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 |
| CZ291440B6 (cs) | 1997-07-08 | 2003-03-12 | H. Lundbeck A/S | Způsob výroby citalopramu |
| UA62985C2 (en) * | 1997-11-10 | 2004-01-15 | Lunnbeck As H | A method for the preparation of citalopram |
| WO1998019512A2 (en) * | 1997-11-11 | 1998-05-14 | H. Lundbeck A/S | Method for the preparation of citalopram |
| WO2000023431A1 (en) | 1998-10-20 | 2000-04-27 | H. Lundbeck A/S | Method for the preparation of citalopram |
| PL203275B1 (pl) | 1998-12-23 | 2009-09-30 | Lundbeck & Co As H | Sposób wytwarzania 5-cyjanoftalidu |
| AR022329A1 (es) | 1999-01-29 | 2002-09-04 | Lundbeck & Co As H | Metodo para la preparacion de 5-cianoftalida |
| ES2195554T5 (es) | 1999-04-14 | 2010-02-02 | H. Lundbeck A/S | Metodo para la preparacion de 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 |
| ITMI991486A1 (it) | 1999-07-06 | 2001-01-06 | Vis Farmaceutici S P A | Processo per la sintesi di citalopram |
| TR200101874T1 (tr) | 1999-10-25 | 2002-02-21 | H. Lundbeck A/S | Sitalopram hazırlanması için yöntem |
| 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 |
| EP1246812B1 (de) | 1999-12-28 | 2004-03-17 | H. Lundbeck A/S | Verfahren zur herstellung von citalopram |
| HUP0203840A3 (en) | 1999-12-30 | 2005-02-28 | Lundbeck & Co As H | Method for the preparation of citalopram |
| ATE252570T1 (de) | 2000-01-14 | 2003-11-15 | Lundbeck & Co As H | Verfahren zur herstellung von 5-cyanophthalid |
| IT1317729B1 (it) | 2000-01-18 | 2003-07-15 | Norpharma S P A | Procedimento per la preparazione della 5-carbossiftalide. |
| US6433196B1 (en) | 2000-02-17 | 2002-08-13 | Sumika Fine Chemicals Co., Ltd. | Production method of citalopram, intermediate therefor and production method of the intermediate |
| 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. |
| 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 |
| GB2357762B (en) | 2000-03-13 | 2002-01-30 | Lundbeck & Co As H | Crystalline base of citalopram |
| KR20020080481A (ko) | 2000-03-13 | 2002-10-23 | 하. 룬트벡 아크티에 셀스카브 | 시탈로프람의 제조 방법 |
| NL1017500C1 (nl) | 2000-03-13 | 2001-04-26 | Lundbeck & Co As H | Werkwijze voor de bereiding van Citalopram. |
| PL357022A1 (en) | 2000-03-13 | 2004-07-12 | H.Lundbeck A/S | Stepwise alkylation of 5-substituted 1-(4-fluorophenyl)-1,3-dihydroisobenzofurans |
| DK1265882T3 (da) | 2000-03-14 | 2004-06-01 | Lundbeck & Co As H | Fremgangsmåde til fremstilling af 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 |
| BR0106976A (pt) | 2000-07-06 | 2002-07-23 | Lundbeck & Co As H | Método para a preparação de 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 |
| WO2001047877A2 (en) | 2000-12-28 | 2001-07-05 | H. Lundbeck A/S | Process for the preparation of pure citalopram |
-
2001
- 2001-05-07 AR ARP010102152A patent/AR032455A1/es active IP Right Grant
- 2001-05-10 MX MXPA02011125A patent/MXPA02011125A/es active IP Right Grant
- 2001-05-10 CN CNB018125859A patent/CN100422166C/zh not_active Expired - Fee Related
- 2001-05-10 JP JP2001582313A patent/JP2003532721A/ja not_active Withdrawn
- 2001-05-10 DK DK01931469T patent/DK1296970T3/da active
- 2001-05-10 PT PT01931469T patent/PT1296970E/pt unknown
- 2001-05-10 IL IL15264501A patent/IL152645A0/xx unknown
- 2001-05-10 SK SK1754-2002A patent/SK287035B6/sk not_active IP Right Cessation
- 2001-05-10 EP EP01931469A patent/EP1296970B1/de not_active Expired - Lifetime
- 2001-05-10 AT AT01931469T patent/ATE389645T1/de not_active IP Right Cessation
- 2001-05-10 AU AU5823901A patent/AU5823901A/xx active Pending
- 2001-05-10 SI SI200130831T patent/SI1296970T1/sl unknown
- 2001-05-10 DE DE60133280T patent/DE60133280T2/de not_active Expired - Fee Related
- 2001-05-10 ES ES01931469T patent/ES2301541T3/es not_active Expired - Lifetime
- 2001-05-10 BR BR0110996-0A patent/BR0110996A/pt not_active Application Discontinuation
- 2001-05-10 NZ NZ522475A patent/NZ522475A/en unknown
- 2001-05-10 CZ CZ20024065A patent/CZ20024065A3/cs unknown
- 2001-05-10 CA CA002408292A patent/CA2408292C/en not_active Expired - Fee Related
- 2001-05-10 WO PCT/DK2001/000333 patent/WO2001085712A1/en active IP Right Grant
- 2001-05-10 HU HU0301942A patent/HUP0301942A2/hu unknown
- 2001-05-10 AU AU2001258239A patent/AU2001258239B2/en not_active Ceased
- 2001-05-10 EA EA200201211A patent/EA005674B1/ru not_active IP Right Cessation
- 2001-05-10 PL PL01358144A patent/PL358144A1/xx unknown
- 2001-10-05 UA UA2002118821A patent/UA72039C2/uk unknown
-
2002
- 2002-10-31 IS IS6605A patent/IS2586B/is unknown
- 2002-11-04 IL IL152645A patent/IL152645A/en not_active IP Right Cessation
- 2002-11-05 ZA ZA200208973A patent/ZA200208973B/en unknown
- 2002-11-08 HR HRP20020881 patent/HRP20020881A2/hr not_active Application Discontinuation
- 2002-11-08 US US10/291,174 patent/US6660873B2/en not_active Expired - Fee Related
- 2002-11-12 NO NO20025423A patent/NO327963B1/no not_active IP Right Cessation
- 2002-12-03 BG BG107349A patent/BG65820B1/bg unknown
-
2003
- 2003-11-20 HK HK03108460.1A patent/HK1056171A1/xx not_active IP Right Cessation
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