UA62985C2 - A method for the preparation of citalopram - Google Patents

A method for the preparation of citalopram Download PDF

Info

Publication number: UA62985C2
Authority: UA; Ukraine
Prior art keywords: compound; formula; carried out; differs; acid
Prior art date: 1997-10-11

Application number

UA2000052907A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Lunnbeck As H

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1997-11-10

Filing date

1997-10-11

Publication date

2004-01-15

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=37709809&utm_source=***_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=UA62985(C2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1997-10-11 Application filed by Lunnbeck As H filed Critical Lunnbeck As H

2004-01-15 Publication of UA62985C2 publication Critical patent/UA62985C2/uk

Links

238000000034 method Methods 0.000 title claims abstract description 39
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
229960001653 citalopram Drugs 0.000 title claims abstract description 25
238000002360 preparation method Methods 0.000 title abstract description 4
150000001875 compounds Chemical class 0.000 claims abstract description 41
238000006243 chemical reaction Methods 0.000 claims abstract description 25
-1 5-cyano compound Chemical class 0.000 claims abstract description 24
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 17
230000029936 alkylation Effects 0.000 claims abstract description 6
238000005804 alkylation reaction Methods 0.000 claims abstract description 6
238000006798 ring closing metathesis reaction Methods 0.000 claims abstract description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 21
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
239000002253 acid Substances 0.000 claims description 12
150000003839 salts Chemical class 0.000 claims description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
150000002148 esters Chemical class 0.000 claims description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 7
150000001408 amides Chemical class 0.000 claims description 7
238000007363 ring formation reaction Methods 0.000 claims description 7
239000000126 substance Substances 0.000 claims description 7
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 5
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 4
150000003973 alkyl amines Chemical class 0.000 claims description 4
229910021529 ammonia Inorganic materials 0.000 claims description 4
230000001430 anti-depressive effect Effects 0.000 claims description 4
230000007062 hydrolysis Effects 0.000 claims description 4
238000006460 hydrolysis reaction Methods 0.000 claims description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
150000007522 mineralic acids Chemical class 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical group CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 claims description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
239000012024 dehydrating agents‎ Substances 0.000 claims description 3
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 3
WNZQDUSMALZDQF-UHFFFAOYSA-N isobenzofuranone Natural products C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 claims description 3
WKCMNQHTRHUMJO-UHFFFAOYSA-N lithium;propan-2-amine Chemical compound [Li].CC(C)N WKCMNQHTRHUMJO-UHFFFAOYSA-N 0.000 claims description 3
150000007524 organic acids Chemical class 0.000 claims description 3
QXCKIEDIBGSMRB-UHFFFAOYSA-N 1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carboxylic acid Chemical class O1CC2=CC(C(=O)O)=CC=C2C1C1=CC=C(F)C=C1 QXCKIEDIBGSMRB-UHFFFAOYSA-N 0.000 claims description 2
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
239000007818 Grignard reagent Substances 0.000 claims description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 2
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims description 2
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
230000009435 amidation Effects 0.000 claims description 2
238000007112 amidation reaction Methods 0.000 claims description 2
125000003368 amide group Chemical group 0.000 claims description 2
230000032050 esterification Effects 0.000 claims description 2
238000005886 esterification reaction Methods 0.000 claims description 2
150000004795 grignard reagents Chemical class 0.000 claims description 2
238000010438 heat treatment Methods 0.000 claims description 2
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-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
230000003993 interaction Effects 0.000 claims 3
NYYRRBOMNHUCLB-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCCl NYYRRBOMNHUCLB-UHFFFAOYSA-N 0.000 claims 1
239000002168 alkylating agent Substances 0.000 claims 1
229940100198 alkylating agent Drugs 0.000 claims 1
OVEHNNQXLPJPPL-UHFFFAOYSA-N lithium;n-propan-2-ylpropan-2-amine Chemical compound [Li].CC(C)NC(C)C OVEHNNQXLPJPPL-UHFFFAOYSA-N 0.000 claims 1
OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 claims 1
229910001623 magnesium bromide Inorganic materials 0.000 claims 1
150000002440 hydroxy compounds Chemical class 0.000 abstract 1
125000004043 oxo group Chemical group O=* 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 11
239000002904 solvent Substances 0.000 description 11
239000002585 base Substances 0.000 description 9
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
239000000935 antidepressant agent Substances 0.000 description 5
235000019439 ethyl acetate Nutrition 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
238000001816 cooling Methods 0.000 description 4
239000012071 phase Substances 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
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 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-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
229940005513 antidepressants Drugs 0.000 description 3
239000013078 crystal Substances 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
229910000042 hydrogen bromide Inorganic materials 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
239000007924 injection Substances 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000011777 magnesium Substances 0.000 description 3
229910052749 magnesium Inorganic materials 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([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
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
AITNMTXHTIIIBB-UHFFFAOYSA-N 1-bromo-4-fluorobenzene Chemical compound FC1=CC=C(Br)C=C1 AITNMTXHTIIIBB-UHFFFAOYSA-N 0.000 description 2
XEEGWTLAFIZLSF-UHFFFAOYSA-N 1-oxo-3h-2-benzofuran-5-carbonitrile Chemical compound N#CC1=CC=C2C(=O)OCC2=C1 XEEGWTLAFIZLSF-UHFFFAOYSA-N 0.000 description 2
QTWUWCFGWYYRRL-UHFFFAOYSA-N 1-oxo-3h-2-benzofuran-5-carboxylic acid Chemical compound OC(=O)C1=CC=C2C(=O)OCC2=C1 QTWUWCFGWYYRRL-UHFFFAOYSA-N 0.000 description 2
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 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
238000003747 Grignard reaction Methods 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
125000000217 alkyl 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
239000003085 diluting agent Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000003480 eluent Substances 0.000 description 2
SEBGAMZSPVFQGZ-UHFFFAOYSA-N ethyl 1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carboxylate Chemical compound O1CC2=CC(C(=O)OCC)=CC=C2C1C1=CC=C(F)C=C1 SEBGAMZSPVFQGZ-UHFFFAOYSA-N 0.000 description 2
RAQLQVDNIKWBRL-UHFFFAOYSA-N ethyl 1-oxo-3h-2-benzofuran-5-carboxylate Chemical compound CCOC(=O)C1=CC=C2C(=O)OCC2=C1 RAQLQVDNIKWBRL-UHFFFAOYSA-N 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
238000002955 isolation Methods 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
BRKADVNLTRCLOW-UHFFFAOYSA-M magnesium;fluorobenzene;bromide Chemical compound [Mg+2].[Br-].FC1=CC=[C-]C=C1 BRKADVNLTRCLOW-UHFFFAOYSA-M 0.000 description 2
239000000203 mixture Substances 0.000 description 2
150000002825 nitriles Chemical class 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000003826 tablet Substances 0.000 description 2
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
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 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
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
244000144725 Amygdalus communis Species 0.000 description 1
235000011437 Amygdalus communis Nutrition 0.000 description 1
244000223760 Cinnamomum zeylanicum Species 0.000 description 1
235000005979 Citrus limon Nutrition 0.000 description 1
244000131522 Citrus pyriformis Species 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
206010012289 Dementia Diseases 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
241000220225 Malus Species 0.000 description 1
235000011430 Malus pumila Nutrition 0.000 description 1
235000015103 Malus silvestris Nutrition 0.000 description 1
101100412856 Mus musculus Rhod gene Proteins 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
101100242191 Tetraodon nigroviridis rho gene Proteins 0.000 description 1
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
241000256856 Vespidae Species 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
ALIGTYPNWJPIKT-UHFFFAOYSA-M [Cl-].FC1=CC=C([Mg+])C=C1 Chemical compound [Cl-].FC1=CC=C([Mg+])C=C1 ALIGTYPNWJPIKT-UHFFFAOYSA-M 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000000654 additive Substances 0.000 description 1
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235000020224 almond Nutrition 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
235000010216 calcium carbonate Nutrition 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
208000026106 cerebrovascular disease Diseases 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 description 1
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238000007796 conventional method Methods 0.000 description 1
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VXROOKJCZCDMMS-UHFFFAOYSA-N dcht Chemical compound CC(=O)OC1C(OC(C)=O)C2(C)CC(C)CCC2C(OC(C)=O)C2CC(=O)C(C)=C1C2(C)C VXROOKJCZCDMMS-UHFFFAOYSA-N 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
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ABNRPSOLOCLXOE-UHFFFAOYSA-N ethyl 4-[(4-fluorophenyl)-hydroxymethyl]-3-(hydroxymethyl)benzoate Chemical compound OCC1=CC(C(=O)OCC)=CC=C1C(O)C1=CC=C(F)C=C1 ABNRPSOLOCLXOE-UHFFFAOYSA-N 0.000 description 1
238000011049 filling Methods 0.000 description 1
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125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000002156 mixing Methods 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
SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
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238000011084 recovery Methods 0.000 description 1
238000010992 reflux Methods 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
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230000002269 spontaneous effect Effects 0.000 description 1
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235000020357 syrup Nutrition 0.000 description 1
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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
230000001256 tonic effect Effects 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- 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
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
- 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
- C07C255/53—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and hydroxy groups bound to the carbon skeleton
- 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

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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Furan Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Steroid Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

UA2000052907A 1997-11-10 1997-10-11 A method for the preparation of citalopram UA62985C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
PCT/DK1997/000511 WO1998019511A2 (en)	1997-11-10	1997-11-10	Method for the preparation of citalopram
CNB971825017A CN100338051C (zh)	1997-11-10	1997-11-10	西酞普兰的制备方法

Publications (1)

Publication Number	Publication Date
UA62985C2 true UA62985C2 (en)	2004-01-15

Family

ID=37709809

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA2000052907A UA62985C2 (en)	1997-11-10	1997-10-11	A method for the preparation of citalopram

Country Status (21)

Country	Link
US (1)	US6291689B1 (ru)
EP (1)	EP1032566B9 (ru)
JP (1)	JP2002530296A (ru)
CN (1)	CN100338051C (ru)
AR (1)	AR029604A2 (ru)
AT (1)	ATE232524T1 (ru)
AU (1)	AU738526C (ru)
BR (1)	BR9714924A (ru)
CA (1)	CA2291068C (ru)
CZ (1)	CZ296533B6 (ru)
DE (2)	DE1032566T1 (ru)
DK (1)	DK1032566T5 (ru)
EA (1)	EA003132B1 (ru)
ES (1)	ES2149141T4 (ru)
IL (1)	IL135813A (ru)
IS (1)	IS5473A (ru)
SK (1)	SK6812000A3 (ru)
TR (1)	TR200001314T2 (ru)
UA (1)	UA62985C2 (ru)
WO (1)	WO1998019511A2 (ru)
ZA (1)	ZA9810059B (ru)

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UA62985C2 (en)	1997-11-10	2004-01-15	Lunnbeck As H	A method for the preparation of citalopram
CZ292911B6 (cs)	1997-11-11	2004-01-14	H. Lundbeck A/S	Způsob výroby citalopramu
PL199423B1 (pl) *	1998-10-20	2008-09-30	Lundbeck & Co As H	Sposób wytwarzania citalopramu
TR200101796T2 (tr)	1998-12-23	2001-11-21	H. Lundbeck A/S	5-Siyanofitalitin preparasyonuna yönelik metot
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
HUP0200169A3 (en) *	1999-10-25	2002-11-28	Lundbeck & Co As H	Method for the preparation of citalopram
GB2360281B (en)	1999-10-25	2002-01-16	Lundbeck & Co As H	Method for the preparation of 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
AR026063A1 (es)	1999-11-01	2002-12-26	Lundbeck & Co As H	Metodo para la preparacion de 5-carboxiftalida.
WO2001047909A1 (en)	1999-12-28	2001-07-05	H. Lundbeck A/S	Method for the preparation of citalopram
PL198803B1 (pl) *	1999-12-30	2008-07-31	Lundbeck & Co As H	Sposób wytwarzania 5-cyjano-3H-izobenzofuran-1-onu
ES2206177T3 (es)	2000-01-14	2004-05-16	H. Lundbeck A/S	Metodo para la preparacion de 5-cianoftalida.
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.
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
IES20010206A2 (en)	2000-03-13	2002-03-06	Lundbeck & Co As H	Method for the preparation of citalopram
BR0109176A (pt) *	2000-03-13	2003-04-22	Lundbeck & Co As H	Método para preparação de citalopram e composto da fórmula
GB2357762B (en) *	2000-03-13	2002-01-30	Lundbeck & Co As H	Crystalline base of citalopram
GR1004072B (el) *	2000-03-13	2002-12-02	H.Lundbeck A/S	Μεθοδος παρασκευης της σιταλοπραμης
CA2402553A1 (en)	2000-03-13	2001-09-20	H. Lundbeck A/S	Stepwise alkylation of 5-substituted 1-(4-fluorophenyl)-1,3-dihydroisobenzofurans
IL151488A0 (en) *	2000-03-14	2003-04-10	Lundbeck & Co As H	Method for the preparation of citalopram
EP1274699A1 (en) *	2000-03-16	2003-01-15	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
CA2354880C (en) *	2000-08-18	2003-06-03	H. Lundbeck A/S	Method for the preparation of citalopram
US6491947B2 (en)	2000-11-03	2002-12-10	Chemlink Laboratories, Llc	Expanded perborate salt, use, and method of production
IT1319686B1 (it) *	2000-12-12	2003-10-23	C D Farmasint S R L	Procedimento di preparazione di citalopram.
IL147226A (en)	2000-12-22	2006-04-10	Lundbeck & Co As H	Process for the preparation of pure cithalopram
PT1181272E (pt) *	2000-12-28	2003-01-31	Lundbeck & Co As H	Processo para a preparacao de citalopram puro
CA2435925A1 (en)	2001-01-30	2002-08-08	Orion Corporation Fermion	Process for the preparation of 1-(3-dimethylaminopropyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile
BG65271B1 (bg) *	2001-06-18	2007-11-30	H. Lundbeck A/S	Метод за получаване на циталопрам
DE60217932T2 (de)	2001-07-31	2007-08-30	H. Lundbeck A/S, Valby	Kristalline Zusammensetzung enthaltend Escitalopram
US7196224B2 (en) *	2002-03-27	2007-03-27	Bando Chemical Industries, Ltd.	1,3,5-tris(arylamino)benzenes
BG65515B1 (bg) *	2002-07-26	2008-10-31	H. Lundbeck A/S	Метод за получаване на 5-цианофталид
FI20021421A0 (fi) *	2002-07-30	2002-07-30	Orion Corp Fermion	Valmistusmenetelmä
PE20040991A1 (es)	2002-08-12	2004-12-27	Lundbeck & Co As H	Separacion de intermediarios para la preparacion de escitalopram
AU2002330730A1 (en) *	2002-08-14	2004-03-03	Natco Pharma Limited	Process for the preparation of high purity citalopram and its pharmaceutically acceptable salts
GB2385051B (en) *	2002-08-29	2003-12-24	Max India Ltd	Improved process for the preparation of 5-substituted-1 (4-fluorophenyl)-1,3-dihydro isobenzofurans
AU2003263155A1 (en) *	2002-09-20	2004-04-08	H. Lundbeck A/S	Method for manufacture of dihydroisobenzofuran derivatives
US6812355B2 (en)	2002-10-22	2004-11-02	Sekhsaria Chemicals Limited	Process for the manufacture of citalopram hydrobromide from 5-bromophthalide
ITMI20030479A1 (it) *	2003-03-13	2004-09-14	Adorkem Technology S P A	Procedimento per la preparazione di un ciano-isobenzofurano.
US7687645B2 (en)	2003-03-21	2010-03-30	H. Lundbeck A/S	Intermediates for the preparation of citalopram and escitalopram
AU2003238676A1 (en) *	2003-04-21	2004-11-19	Podile Khadgapathi	An improved process for the preparation of citalopram hydrobromide
US6781003B1 (en) *	2003-06-09	2004-08-24	Aurobindo Pharma Ltd.	Preparation of pure citalopram
ATE293106T1 (de) *	2003-10-28	2005-04-15	Adorkem Technology Spa	Verfahren zur herstellung von citalopram
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
CA2559703A1 (en) *	2004-02-16	2005-08-25	Jubilant Organosys Limited	One pot synthesis of citalopram from 5-cyanophthalide
KR101166280B1 (ko)	2004-08-23	2013-11-27	썬 파마 글로벌 에프제트이	시탈로프램 및 에난티오머의 제조 방법
GB0601286D0 (en)	2006-01-23	2006-03-01	Sandoz Ag	Asymmetric synthesis
US9339500B2 (en) *	2008-03-04	2016-05-17	Intra-Cellular Therapies, Inc.	Methods of treating vasomotor symptoms

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GB1143702A (ru) *	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
TW397831B (en) *	1994-07-15	2000-07-11	Meiji Seika Kaisha	The anti-platelet-agglutination hexahydrogenated pyridine and its derivatives
JP3526581B2 (ja)	1997-07-08	2004-05-17	ハー・ルンドベック・アクティーゼルスカブ	シタロプラムの製造方法
UA62985C2 (en)	1997-11-10	2004-01-15	Lunnbeck As H	A method for the preparation of citalopram
CZ292911B6 (cs)	1997-11-11	2004-01-14	H. Lundbeck A/S	Způsob výroby citalopramu

1997
- 1997-10-11 UA UA2000052907A patent/UA62985C2/uk unknown
- 1997-11-10 SK SK681-2000A patent/SK6812000A3/sk unknown
- 1997-11-10 EA EA200000509A patent/EA003132B1/ru not_active IP Right Cessation
- 1997-11-10 JP JP2000583316A patent/JP2002530296A/ja active Pending
- 1997-11-10 CZ CZ20001713A patent/CZ296533B6/cs not_active IP Right Cessation
- 1997-11-10 DE DE1032566T patent/DE1032566T1/de active Pending
- 1997-11-10 DE DE69719098T patent/DE69719098T2/de not_active Revoked
- 1997-11-10 EP EP97945798A patent/EP1032566B9/en not_active Revoked
- 1997-11-10 CA CA002291068A patent/CA2291068C/en not_active Expired - Fee Related
- 1997-11-10 AU AU51167/98A patent/AU738526C/en not_active Ceased
- 1997-11-10 BR BR9714924-1A patent/BR9714924A/pt not_active Application Discontinuation
- 1997-11-10 IL IL13581397A patent/IL135813A/xx not_active IP Right Cessation
- 1997-11-10 CN CNB971825017A patent/CN100338051C/zh not_active Expired - Fee Related
- 1997-11-10 ES ES97945798T patent/ES2149141T4/es not_active Expired - Lifetime
- 1997-11-10 TR TR2000/01314T patent/TR200001314T2/xx unknown
- 1997-11-10 DK DK97945798T patent/DK1032566T5/da active
- 1997-11-10 WO PCT/DK1997/000511 patent/WO1998019511A2/en not_active Application Discontinuation
- 1997-11-10 AT AT97945798T patent/ATE232524T1/de not_active IP Right Cessation
1998
- 1998-11-03 ZA ZA9810059A patent/ZA9810059B/xx unknown
1999
- 1999-10-22 AR ARP990105341A patent/AR029604A2/es unknown
2000
- 2000-04-26 IS IS5473A patent/IS5473A/is unknown
- 2000-05-03 US US09/565,061 patent/US6291689B1/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
ZA9810059B (en)	1999-05-05
IS5473A (is)	2000-04-26
BR9714924A (pt)	2000-09-26
DE1032566T1 (de)	2001-03-15
ATE232524T1 (de)	2003-02-15
AU738526C (en)	2004-03-25
WO1998019511A3 (en)	1998-08-06
CZ296533B6 (cs)	2006-04-12
ES2149141T3 (es)	2003-10-01
DE69719098D1 (de)	2003-03-20
CA2291068C (en)	2002-10-29
EA003132B1 (ru)	2003-02-27
ES2149141T1 (es)	2000-11-01
SK6812000A3 (en)	2000-10-09
EP1032566A2 (en)	2000-09-06
IL135813A (en)	2003-07-31
ES2149141T4 (es)	2004-11-16
EA200000509A1 (ru)	2000-10-30
IL135813A0 (en)	2001-05-20
CN100338051C (zh)	2007-09-19
AU5116798A (en)	1998-05-29
AU738526B2 (en)	2001-09-20
DE69719098T2 (de)	2004-02-12
AR029604A2 (es)	2003-07-10
US6291689B1 (en)	2001-09-18
WO1998019511A2 (en)	1998-05-14
CA2291068A1 (en)	1998-05-14
EP1032566B9 (en)	2003-10-22
CZ20001713A3 (cs)	2000-10-11
TR200001314T2 (tr)	2000-11-21
DK1032566T5 (da)	2004-06-28
CN1286688A (zh)	2001-03-07
JP2002530296A (ja)	2002-09-17
DK1032566T3 (da)	2003-06-10
EP1032566B1 (en)	2003-02-12

Publication	Publication Date	Title
UA62985C2 (en)	2004-01-15	A method for the preparation of citalopram
EA001728B1 (ru)	2001-08-27	Способ получения циталопрама
JP3447267B2 (ja)	2003-09-16	シタロプラムの製造方法
UA62984C2 (en)	2004-01-15	A method for the preparation of citalopram
SK13132002A3 (sk)	2003-01-09	Spôsob výroby soli citalopramu, kryštalická báza citalopramu a soli citalopramu a farmaceutický prostriedok s ich obsahom
EA004033B1 (ru)	2003-12-25	Способ получения циталопрама
UA72340C2 (ru)	2005-02-15	Способ получения циталопрама
ITMI20010386A1 (it)	2002-08-26	Metodo per la preparazione di citalopram
SK17542002A3 (sk)	2003-04-01	Spôsob prípravy citalopramu, medziprodukt a antidepresívny farmaceutický prostriedok s obsahom citalopramu
MXPA02008634A (es)	2003-02-24	Metodo para la preparacion de citalopram.
CZ20023383A3 (cs)	2003-01-15	Způsob výroby citalopramu
KR100466463B1 (ko)	2005-01-13	시탈로프람의 제조방법
BG104487A (bg)	2001-01-31	Метод за получаване на циталопрам
CN1138768C (zh)	2004-02-18	氰酞氟苯胺的制备方法
PL195626B1 (pl)	2007-10-31	Sposób wytwarzania citalopramu oraz związki pośrednie
MXPA00004510A (en)	2001-07-09	Method for the preparation of citalopram