NO326772B1 - Fremgangsmate for fremstilling av Citalopram - Google Patents
Fremgangsmate for fremstilling av Citalopram Download PDFInfo
- Publication number
- NO326772B1 NO326772B1 NO20013942A NO20013942A NO326772B1 NO 326772 B1 NO326772 B1 NO 326772B1 NO 20013942 A NO20013942 A NO 20013942A NO 20013942 A NO20013942 A NO 20013942A NO 326772 B1 NO326772 B1 NO 326772B1
- Authority
- NO
- Norway
- Prior art keywords
- alkyl
- aryl
- compound
- formula
- alkylamino
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 42
- 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 description 26
- 229960001653 citalopram Drugs 0.000 title claims description 26
- 238000002360 preparation method Methods 0.000 title description 4
- -1 cyano, hydroxy Chemical group 0.000 claims description 60
- 150000001875 compounds Chemical class 0.000 claims description 55
- 125000003118 aryl group Chemical group 0.000 claims description 46
- 125000001072 heteroaryl group Chemical group 0.000 claims description 43
- 125000003282 alkyl amino group Chemical group 0.000 claims description 42
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 36
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 36
- 229910052736 halogen Inorganic materials 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 22
- 150000002367 halogens Chemical class 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 11
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 10
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 8
- 239000012024 dehydrating agents Substances 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 7
- 229920002554 vinyl polymer Polymers 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 150000004820 halides Chemical class 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 5
- 125000004104 aryloxy group Chemical group 0.000 claims description 5
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 claims description 5
- 125000002524 organometallic group Chemical group 0.000 claims description 5
- 229940124530 sulfonamide Drugs 0.000 claims description 5
- 150000003456 sulfonamides Chemical class 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 229910052759 nickel Inorganic materials 0.000 claims description 4
- 150000002900 organolithium compounds Chemical class 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 230000008878 coupling Effects 0.000 claims description 3
- 238000010168 coupling process Methods 0.000 claims description 3
- 238000005859 coupling reaction Methods 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 2
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims description 2
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 14
- 101710178035 Chorismate synthase 2 Proteins 0.000 claims 2
- 101710152694 Cysteine synthase 2 Proteins 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims 2
- 229910019213 POCl3 Inorganic materials 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 239000011777 magnesium Substances 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000000935 antidepressant agent Substances 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 239000013067 intermediate product Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000006798 ring closing metathesis reaction Methods 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-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
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 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
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 230000000694 effects Effects 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
- GECQEQCYCDJXJC-UHFFFAOYSA-N 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-3h-2-benzofuran-5-carboxylic acid Chemical compound O1CC2=CC(C(O)=O)=CC=C2C1(CCCN(C)C)C1=CC=C(F)C=C1 GECQEQCYCDJXJC-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
- WOLPGGGWZDXCNM-UHFFFAOYSA-N 3-[5-bromo-1-(4-fluorophenyl)-3h-2-benzofuran-1-yl]-n,n-dimethylpropan-1-amine Chemical compound O1CC2=CC(Br)=CC=C2C1(CCCN(C)C)C1=CC=C(F)C=C1 WOLPGGGWZDXCNM-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000007818 Grignard reagent Substances 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 229910021380 Manganese Chloride Inorganic materials 0.000 description 2
- GLFNIEUTAYBVOC-UHFFFAOYSA-L Manganese chloride Chemical compound Cl[Mn]Cl GLFNIEUTAYBVOC-UHFFFAOYSA-L 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 125000005910 alkyl carbonate group Chemical group 0.000 description 2
- 230000001430 anti-depressive effect Effects 0.000 description 2
- 229940005513 antidepressants Drugs 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000007796 conventional method Methods 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
- 238000006297 dehydration reaction Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 150000004795 grignard reagents Chemical class 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 229910052749 magnesium Inorganic materials 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
- IUYHWZFSGMZEOG-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].C[CH-]C IUYHWZFSGMZEOG-UHFFFAOYSA-M 0.000 description 2
- 239000011565 manganese chloride Substances 0.000 description 2
- 235000002867 manganese chloride Nutrition 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000001979 organolithium group Chemical group 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- IUXHPSPHPKXTPA-ONEGZZNKSA-N (e)-1-bromobut-1-ene Chemical compound CC\C=C\Br IUXHPSPHPKXTPA-ONEGZZNKSA-N 0.000 description 1
- 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
- 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
- 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
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 1
- NYYRRBOMNHUCLB-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCCl NYYRRBOMNHUCLB-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
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-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
- SKTFQHRVFFOHTQ-UHFFFAOYSA-N 8-bromo-1,3-dimethyl-7h-purine-2,6-dione Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC(Br)=N2 SKTFQHRVFFOHTQ-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 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
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- IWYHZMPXXYOJPU-UHFFFAOYSA-M CN(C)CCCC1(OCc2cc([Mg]Br)ccc12)c1ccc(F)cc1 Chemical compound CN(C)CCCC1(OCc2cc([Mg]Br)ccc12)c1ccc(F)cc1 IWYHZMPXXYOJPU-UHFFFAOYSA-M 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 206010012289 Dementia Diseases 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 101000939500 Homo sapiens UBX domain-containing protein 11 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
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N Theophylline Natural products O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 102100029645 UBX domain-containing protein 11 Human genes 0.000 description 1
- GWFKSQSXNUNYAC-AATRIKPKSA-N [(e)-hex-1-enyl]boronic acid Chemical compound CCCC\C=C\B(O)O GWFKSQSXNUNYAC-AATRIKPKSA-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
- 239000000908 ammonium hydroxide Substances 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
- 125000005605 benzo group Chemical group 0.000 description 1
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- PQLFROTZSIMBKR-UHFFFAOYSA-N ethenyl carbonochloridate Chemical compound ClC(=O)OC=C PQLFROTZSIMBKR-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine 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
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- LBSANEJBGMCTBH-UHFFFAOYSA-N manganate Chemical class [O-][Mn]([O-])(=O)=O LBSANEJBGMCTBH-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- OBWFJXLKRAFEDI-UHFFFAOYSA-N methyl cyanoformate Chemical compound COC(=O)C#N OBWFJXLKRAFEDI-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- GRSBAMVBFWRBBH-UHFFFAOYSA-N o-ethyl chloromethanethioate Chemical compound CCOC(Cl)=S GRSBAMVBFWRBBH-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- UWBHMRBRLOJJAA-UHFFFAOYSA-N oxaluric acid Chemical compound NC(=O)NC(=O)C(O)=O UWBHMRBRLOJJAA-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- WXHIJDCHNDBCNY-UHFFFAOYSA-N palladium dihydride Chemical compound [PdH2] WXHIJDCHNDBCNY-UHFFFAOYSA-N 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- SFLGSKRGOWRGBR-UHFFFAOYSA-N phthalane Chemical class C1=CC=C2COCC2=C1 SFLGSKRGOWRGBR-UHFFFAOYSA-N 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UCIWHYOLUNVRJP-UHFFFAOYSA-N prop-1-enyl trifluoromethanesulfonate Chemical compound CC=COS(=O)(=O)C(F)(F)F UCIWHYOLUNVRJP-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
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- JZWFDVDETGFGFC-UHFFFAOYSA-N salacetamide Chemical group CC(=O)NC(=O)C1=CC=CC=C1O JZWFDVDETGFGFC-UHFFFAOYSA-N 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
- 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
- RHIQJVDJCXNLSP-UHFFFAOYSA-N trimethyl(prop-1-enyl)stannane Chemical compound CC=C[Sn](C)(C)C RHIQJVDJCXNLSP-UHFFFAOYSA-N 0.000 description 1
- 239000003039 volatile agent 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
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/34—Tobacco-abuse
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)
- Addiction (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Furan Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA200001231 | 2000-08-18 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20013942D0 NO20013942D0 (no) | 2001-08-14 |
| NO20013942L NO20013942L (no) | 2002-02-19 |
| NO326772B1 true NO326772B1 (no) | 2009-02-16 |
Family
ID=8159660
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20013942A NO326772B1 (no) | 2000-08-18 | 2001-08-14 | Fremgangsmate for fremstilling av Citalopram |
| NO20013943A NO326570B1 (no) | 2000-08-18 | 2001-08-14 | Fremgangsmate for fremstilling av Citalopram |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20013943A NO326570B1 (no) | 2000-08-18 | 2001-08-14 | Fremgangsmate for fremstilling av Citalopram |
Country Status (41)
| Country | Link |
|---|---|
| US (2) | US6426422B1 (de) |
| EP (2) | EP1309581B1 (de) |
| JP (2) | JP2004506729A (de) |
| KR (2) | KR100887206B1 (de) |
| CN (3) | CN1222517C (de) |
| AR (3) | AR029597A1 (de) |
| AT (4) | ATE281447T1 (de) |
| AU (6) | AU7960901A (de) |
| BE (2) | BE1013443A6 (de) |
| BG (2) | BG65965B1 (de) |
| CA (2) | CA2354877C (de) |
| CH (2) | CH691968A5 (de) |
| CL (2) | CL2008002412A1 (de) |
| CZ (2) | CZ295863B6 (de) |
| DE (4) | DE60106932T2 (de) |
| DK (4) | DK200101216A (de) |
| EA (2) | EA005946B1 (de) |
| ES (4) | ES2230347T3 (de) |
| FI (2) | FI20011622A (de) |
| FR (2) | FR2813078B1 (de) |
| GB (2) | GB2365865B (de) |
| GR (1) | GR1004074B (de) |
| HK (3) | HK1044538B (de) |
| HR (2) | HRP20030064A2 (de) |
| HU (2) | HUP0103291A3 (de) |
| IE (2) | IES20010761A2 (de) |
| IL (2) | IL144817A0 (de) |
| IS (2) | IS2121B (de) |
| ME (2) | MEP2208A (de) |
| MX (2) | MXPA03000913A (de) |
| NL (2) | NL1018776C1 (de) |
| NO (2) | NO326772B1 (de) |
| NZ (2) | NZ523853A (de) |
| PL (2) | PL359825A1 (de) |
| PT (2) | PT1309582E (de) |
| RS (2) | RS50287B (de) |
| SI (2) | SI1309581T1 (de) |
| SK (2) | SK287008B6 (de) |
| UA (2) | UA71676C2 (de) |
| WO (2) | WO2002016341A1 (de) |
| ZA (1) | ZA200106683B (de) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR022329A1 (es) | 1999-01-29 | 2002-09-04 | Lundbeck & Co As H | Metodo para la preparacion de 5-cianoftalida |
| EA004033B1 (ru) | 1999-04-14 | 2003-12-25 | Х.Лундбекк А/С | Способ получения циталопрама |
| ITMI991581A1 (it) * | 1999-06-25 | 2001-01-15 | Lundbeck & Co As H | Metodo per la preparazione di citalopram |
| ATE355268T1 (de) | 1999-10-25 | 2006-03-15 | Lundbeck & Co As H | Verfahren zur herstellung von citalopram |
| AR026063A1 (es) | 1999-11-01 | 2002-12-26 | Lundbeck & Co As H | Metodo para la preparacion de 5-carboxiftalida. |
| ES2219095T3 (es) | 1999-12-28 | 2004-11-16 | H. Lundbeck A/S | Metodo para la preparacion de citalopram. |
| UA73336C2 (en) | 1999-12-30 | 2005-07-15 | Lundbeck & Co As H | A method for the preparation of 5-cyano-phtalid |
| ES2206177T3 (es) * | 2000-01-14 | 2004-05-16 | H. Lundbeck A/S | Metodo para la preparacion de 5-cianoftalida. |
| IES20010157A2 (en) | 2000-03-03 | 2002-03-06 | Lundbeck & Co As H | Method for the preparation of citalopram |
| IES20010206A2 (en) | 2000-03-13 | 2002-03-06 | Lundbeck & Co As H | Method for the preparation of citalopram |
| EP1265883A1 (de) * | 2000-03-13 | 2002-12-18 | H. Lundbeck A/S | Verfahren zur herstellung von citalopram |
| CZ20023100A3 (cs) * | 2000-03-13 | 2003-02-12 | H. Lundbeck A/S | Způsob výroby citalopramu |
| DE60101786T2 (de) | 2000-03-14 | 2004-07-15 | H. Lundbeck A/S, Valby | Verfahren zur herstellung von citalopram |
| AU2001244086A1 (en) * | 2000-03-16 | 2001-09-24 | H. Lundbeck A/S | Method for the preparation of 5-cyano-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 |
| FI20011622A (fi) | 2000-08-18 | 2002-02-19 | Lundbeck & Co As H | Menetelmä sitalopraamin valmistamiseksi |
| TR200201166T1 (tr) | 2000-12-22 | 2002-10-21 | H.Lundbecks A/S | Saf sitalopram hazırlanması için yöntem |
| US7148364B2 (en) * | 2002-01-07 | 2006-12-12 | Sun Pharmaceutical Industries | Process for the preparation of 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofuran carbonitrile |
| PE20040991A1 (es) * | 2002-08-12 | 2004-12-27 | Lundbeck & Co As H | Separacion de intermediarios para la preparacion de escitalopram |
| AU2003223105A1 (en) * | 2003-03-24 | 2004-10-18 | Hetero Drugs Limited | Novel crystalline forms of (s)-citalopram oxalate |
| US20050143350A1 (en) * | 2003-11-19 | 2005-06-30 | Seed John C. | Combination drug therapy to treat obesity |
| CN100569765C (zh) | 2003-12-19 | 2009-12-16 | 杭州民生药业集团有限公司 | 西酞普兰中间体晶体碱 |
| US9339500B2 (en) * | 2008-03-04 | 2016-05-17 | Intra-Cellular Therapies, Inc. | Methods of treating vasomotor symptoms |
| US20100087664A1 (en) * | 2008-10-07 | 2010-04-08 | Ravindra Vedantham | Preparation of citalopram and salts thereof |
| JP6222973B2 (ja) * | 2013-04-19 | 2017-11-01 | 日本テルペン化学株式会社 | ジベンジルトリチオカーボネート誘導体 |
| CN103936702A (zh) * | 2014-05-07 | 2014-07-23 | 成都诺维尔生物医药有限公司 | 艾司西酞普兰杂质j的合成方法 |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1143702A (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 |
| 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 |
| DK213290D0 (da) | 1990-09-06 | 1990-09-06 | Lundbeck & Co As H | Treatment of cerebrovascular disorders |
| DE19626659A1 (de) | 1996-07-03 | 1998-01-08 | Basf Ag | Verfahren zur Herstellung von Phthaliden |
| DE19627697A1 (de) | 1996-07-10 | 1998-01-15 | Basf Ag | Verfahren zur Herstellung von Phthaliden |
| ZA9711376B (en) | 1996-12-20 | 1998-07-21 | Lundbeck & Co As H | Indole or dihydroindole derivatives |
| DE69801764T2 (de) | 1997-07-08 | 2002-07-04 | Lundbeck & Co As H | Verfahren zur herstellung von citalopram |
| UA62985C2 (en) * | 1997-11-10 | 2004-01-15 | Lunnbeck As H | A method for the preparation of citalopram |
| DE69714480T2 (de) * | 1997-11-11 | 2003-03-06 | Lundbeck & Co As H | Verfahren zur Herstellung von Citalopram |
| PL199423B1 (pl) | 1998-10-20 | 2008-09-30 | Lundbeck & Co As H | Sposób wytwarzania citalopramu |
| JP2002533450A (ja) * | 1998-12-23 | 2002-10-08 | ハー・ルンドベック・アクチエゼルスカベット | ５−シアノフタリドの製造方法 |
| AR022329A1 (es) | 1999-01-29 | 2002-09-04 | Lundbeck & Co As H | Metodo para la preparacion de 5-cianoftalida |
| EA004033B1 (ru) | 1999-04-14 | 2003-12-25 | Х.Лундбекк А/С | Способ получения циталопрама |
| ITMI991581A1 (it) | 1999-06-25 | 2001-01-15 | Lundbeck & Co As H | Metodo per la preparazione di citalopram |
| ITMI991579A1 (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. |
| 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 |
| IES20010143A2 (en) | 2000-02-24 | 2001-07-25 | Lundbeck & Co As H | Method for the preparation of citalopram |
| FR2805812A1 (fr) | 2000-02-24 | 2001-09-07 | Lundbeck & Co As H | Procede de preparation du 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 |
| TR200201166T1 (tr) | 2000-12-22 | 2002-10-21 | H.Lundbecks A/S | Saf sitalopram hazırlanması için yöntem |
| TR200200018T1 (tr) | 2000-12-28 | 2002-06-21 | H. Lundbeck A/S | Saf sitalopram hazırlanması için yöntem. |
-
2001
- 2001-08-09 FI FI20011622A patent/FI20011622A/fi unknown
- 2001-08-09 FI FI20011621A patent/FI20011621A/fi unknown
- 2001-08-09 IL IL14481701A patent/IL144817A0/xx not_active IP Right Cessation
- 2001-08-09 CA CA002354877A patent/CA2354877C/en not_active Expired - Fee Related
- 2001-08-09 CA CA002354880A patent/CA2354880C/en not_active Expired - Fee Related
- 2001-08-09 IL IL14481601A patent/IL144816A/xx not_active IP Right Cessation
- 2001-08-10 HU HU0103291A patent/HUP0103291A3/hu unknown
- 2001-08-10 IS IS6048A patent/IS2121B/is unknown
- 2001-08-10 IS IS6047A patent/IS2120B/is unknown
- 2001-08-13 IE IE20010761A patent/IES20010761A2/en not_active IP Right Cessation
- 2001-08-13 HU HU0103295A patent/HUP0103295A3/hu unknown
- 2001-08-13 IE IE20010760A patent/IES20010760A2/en not_active IP Right Cessation
- 2001-08-14 DK DK200101216A patent/DK200101216A/da not_active Application Discontinuation
- 2001-08-14 ES ES01957785T patent/ES2230347T3/es not_active Expired - Lifetime
- 2001-08-14 DE DE60106932T patent/DE60106932T2/de not_active Expired - Lifetime
- 2001-08-14 MX MXPA03000913A patent/MXPA03000913A/es active IP Right Grant
- 2001-08-14 PL PL35982501A patent/PL359825A1/xx not_active Application Discontinuation
- 2001-08-14 GR GR20010100398A patent/GR1004074B/el unknown
- 2001-08-14 PL PL35996901A patent/PL359969A1/xx not_active Application Discontinuation
- 2001-08-14 PT PT01957786T patent/PT1309582E/pt unknown
- 2001-08-14 DK DK01957786T patent/DK1309582T3/da active
- 2001-08-14 US US09/930,107 patent/US6426422B1/en not_active Expired - Fee Related
- 2001-08-14 ES ES01957786T patent/ES2228920T3/es not_active Expired - Lifetime
- 2001-08-14 EA EA200300279A patent/EA005946B1/ru not_active IP Right Cessation
- 2001-08-14 JP JP2002521442A patent/JP2004506729A/ja not_active Withdrawn
- 2001-08-14 AU AU7960901A patent/AU7960901A/xx active Pending
- 2001-08-14 ZA ZA200106683A patent/ZA200106683B/xx unknown
- 2001-08-14 RS YUP-115/03A patent/RS50287B/sr unknown
- 2001-08-14 DK DK01957785T patent/DK1309581T3/da active
- 2001-08-14 NZ NZ523853A patent/NZ523853A/en unknown
- 2001-08-14 GB GB0119734A patent/GB2365865B/en not_active Expired - Fee Related
- 2001-08-14 MX MXPA03001329A patent/MXPA03001329A/es active IP Right Grant
- 2001-08-14 AT AT01957785T patent/ATE281447T1/de not_active IP Right Cessation
- 2001-08-14 DK DK200101219A patent/DK200101219A/da not_active Application Discontinuation
- 2001-08-14 NO NO20013942A patent/NO326772B1/no not_active IP Right Cessation
- 2001-08-14 SK SK322-2003A patent/SK287008B6/sk not_active IP Right Cessation
- 2001-08-14 SI SI200130273T patent/SI1309581T1/xx unknown
- 2001-08-14 SK SK320-2003A patent/SK287236B6/sk not_active IP Right Cessation
- 2001-08-14 JP JP2002521443A patent/JP2004506730A/ja not_active Withdrawn
- 2001-08-14 EP EP01957785A patent/EP1309581B1/de not_active Expired - Lifetime
- 2001-08-14 EA EA200300277A patent/EA005811B1/ru not_active IP Right Cessation
- 2001-08-14 WO PCT/DK2001/000541 patent/WO2002016341A1/en active IP Right Grant
- 2001-08-14 KR KR1020037002005A patent/KR100887206B1/ko not_active IP Right Cessation
- 2001-08-14 ME MEP-22/08A patent/MEP2208A/xx unknown
- 2001-08-14 ME MEP-23/08A patent/MEP2308A/xx unknown
- 2001-08-14 NZ NZ523877A patent/NZ523877A/en unknown
- 2001-08-14 UA UA2003010798A patent/UA71676C2/uk unknown
- 2001-08-14 GB GB0119733A patent/GB2362647B/en not_active Expired - Fee Related
- 2001-08-14 UA UA2003010797A patent/UA72340C2/uk unknown
- 2001-08-14 DE DE60106933T patent/DE60106933T2/de not_active Expired - Lifetime
- 2001-08-14 EP EP01957786A patent/EP1309582B1/de not_active Expired - Lifetime
- 2001-08-14 AU AU2001279608A patent/AU2001279608B2/en not_active Ceased
- 2001-08-14 WO PCT/DK2001/000542 patent/WO2002016342A1/en active IP Right Grant
- 2001-08-14 AU AU2001279609A patent/AU2001279609B2/en not_active Ceased
- 2001-08-14 AU AU7960801A patent/AU7960801A/xx active Pending
- 2001-08-14 KR KR1020037001900A patent/KR100887207B1/ko not_active IP Right Cessation
- 2001-08-14 SI SI200130272T patent/SI1309582T1/xx unknown
- 2001-08-14 AT AT01957786T patent/ATE281448T1/de not_active IP Right Cessation
- 2001-08-14 US US09/930,110 patent/US6509483B2/en not_active Expired - Fee Related
- 2001-08-14 NO NO20013943A patent/NO326570B1/no not_active IP Right Cessation
- 2001-08-14 RS YU6903A patent/RS50258B/sr unknown
- 2001-08-14 PT PT01957785T patent/PT1309581E/pt unknown
- 2001-08-15 AU AU2001100271A patent/AU2001100271B4/en not_active Expired
- 2001-08-15 CZ CZ20012959A patent/CZ295863B6/cs not_active IP Right Cessation
- 2001-08-15 CZ CZ20012958A patent/CZ294746B6/cs not_active IP Right Cessation
- 2001-08-16 NL NL1018776A patent/NL1018776C1/nl not_active IP Right Cessation
- 2001-08-16 FR FR0110857A patent/FR2813078B1/fr not_active Expired - Fee Related
- 2001-08-16 AU AU2001100278A patent/AU2001100278B4/en not_active Expired
- 2001-08-16 BE BE2001/0548A patent/BE1013443A6/fr not_active IP Right Cessation
- 2001-08-16 FR FR0110855A patent/FR2813077B1/fr not_active Expired - Fee Related
- 2001-08-16 CH CH01521/01A patent/CH691968A5/de not_active IP Right Cessation
- 2001-08-16 DE DE10140029A patent/DE10140029A1/de not_active Withdrawn
- 2001-08-16 CH CH01522/01A patent/CH691969A5/de not_active IP Right Cessation
- 2001-08-16 AR ARP010103923A patent/AR029597A1/es not_active Application Discontinuation
- 2001-08-16 NL NL1018775A patent/NL1018775C1/nl not_active IP Right Cessation
- 2001-08-16 DE DE10140028A patent/DE10140028A1/de not_active Withdrawn
- 2001-08-16 AR ARP010103924A patent/AR029598A1/es not_active Application Discontinuation
- 2001-08-17 AT AT0065101U patent/AT5026U1/de not_active IP Right Cessation
- 2001-08-17 ES ES200101919A patent/ES2170734B2/es not_active Expired - Fee Related
- 2001-08-17 CN CNB011339489A patent/CN1222517C/zh not_active Expired - Fee Related
- 2001-08-17 CN CNB011339470A patent/CN1159307C/zh not_active Expired - Fee Related
- 2001-08-17 CN CNB2004100018711A patent/CN1239490C/zh not_active Expired - Fee Related
- 2001-08-17 AT AT0065001U patent/AT4946U1/de not_active IP Right Cessation
- 2001-08-17 ES ES200101920A patent/ES2170735B2/es not_active Expired - Fee Related
- 2001-08-20 BE BE2001/0550A patent/BE1013444A6/fr not_active IP Right Cessation
-
2002
- 2002-08-22 HK HK02106176.1A patent/HK1044538B/zh not_active IP Right Cessation
- 2002-09-04 HK HK02106522.2A patent/HK1047086B/zh not_active IP Right Cessation
- 2002-09-04 HK HK05100254A patent/HK1068069A1/xx not_active IP Right Cessation
-
2003
- 2003-02-03 HR HR20030064A patent/HRP20030064A2/xx not_active Application Discontinuation
- 2003-02-03 HR HR20030065A patent/HRP20030065A2/xx not_active Application Discontinuation
- 2003-02-24 BG BG107584A patent/BG65965B1/bg unknown
- 2003-02-24 BG BG107583A patent/BG65964B1/bg unknown
-
2008
- 2008-04-25 AR ARP080101772A patent/AR066694A2/es unknown
- 2008-08-14 CL CL2008002412A patent/CL2008002412A1/es unknown
- 2008-09-09 CL CL2008002673A patent/CL2008002673A1/es unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NO326772B1 (no) | Fremgangsmate for fremstilling av Citalopram | |
| BR9917368B1 (pt) | mÉtodo para preparaÇço de citalopram. | |
| NO327719B1 (no) | Fremgangsmate for fremstilling av citalopram, samt mellomprodukter for fremstilling av det samme | |
| AU2001279608A1 (en) | Method for the preparation of citalopram | |
| NO325185B1 (no) | Fremgangsmate ved fremstilling av citalopram | |
| ES2301541T3 (es) | Metodo para la preparacion de citalopram. | |
| ITMI20011785A1 (it) | Metodo per la preparazione di citalopram |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| CREP | Change of representative |
Representative=s name: PLOUGMANN & VINGTOFT, POSTBOKS 1003 SENTRUM, 0104 |
|
| MM1K | Lapsed by not paying the annual fees |