SK3362002A3 - Method for the preparation of citalopram - Google Patents

Method for the preparation of citalopram Download PDF

Info

Publication number: SK3362002A3
Authority: SK; Slovakia
Prior art keywords: solution; compound; formula; citalopram; fluorophenyl
Prior art date: 2000-07-06

Application number

SK336-2002A

Other languages

English (en)

Slovak (sk)

Inventor

Eva Bolzonella

Andrea Castellin

Andrea Nicole

Original Assignee

Lundbeck & Co 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.)

2000-07-06

Filing date

2001-07-06

Publication date

2002-08-06

2000-07-06 Priority claimed from PCT/EP2000/006426 external-priority patent/WO2001002383A2/en

2001-07-06 Application filed by Lundbeck & Co As H filed Critical Lundbeck & Co As H

2002-08-06 Publication of SK3362002A3 publication Critical patent/SK3362002A3/sk

Links

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
238000000034 method Methods 0.000 title claims abstract description 21
238000002360 preparation method Methods 0.000 title claims description 5
150000001875 compounds Chemical class 0.000 claims abstract description 20
239000007818 Grignard reagent Substances 0.000 claims abstract description 8
150000004795 grignard reagents Chemical class 0.000 claims abstract description 8
239000011777 magnesium Substances 0.000 claims abstract description 8
229910052749 magnesium Inorganic materials 0.000 claims abstract description 8
150000002680 magnesium Chemical class 0.000 claims abstract description 7
239000000203 mixture Substances 0.000 claims description 11
-1 3-dimethylaminopropyl Chemical group 0.000 claims description 8
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 claims description 7
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 6
239000003960 organic solvent Substances 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
238000006243 chemical reaction Methods 0.000 abstract description 8
CGVBIXZVEMXIQU-UHFFFAOYSA-N 3-[1-(4-fluorophenyl)-3h-2-benzofuran-1-yl]-n,n-dimethylpropan-1-amine Chemical compound O1CC2=CC=CC=C2C1(CCCN(C)C)C1=CC=C(F)C=C1 CGVBIXZVEMXIQU-UHFFFAOYSA-N 0.000 abstract description 4
238000004519 manufacturing process Methods 0.000 abstract description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
238000003756 stirring Methods 0.000 description 7
125000004093 cyano group Chemical group *C#N 0.000 description 6
239000000047 product Substances 0.000 description 6
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
239000002904 solvent Substances 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
229910001623 magnesium bromide Inorganic materials 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
JONIMGVUGJVFQD-UHFFFAOYSA-N (4-methylphenyl)sulfonylformonitrile Chemical compound CC1=CC=C(S(=O)(=O)C#N)C=C1 JONIMGVUGJVFQD-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
239000000935 antidepressant agent Substances 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
239000000284 extract Substances 0.000 description 3
VMJNTFXCTXAXTC-UHFFFAOYSA-N 2,2-difluoro-1,3-benzodioxole-5-carbonitrile Chemical group C1=C(C#N)C=C2OC(F)(F)OC2=C1 VMJNTFXCTXAXTC-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
125000004457 alkyl amino carbonyl group Chemical group 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
230000001430 anti-depressive effect Effects 0.000 description 2
JPUHPGALPBINPO-UHFFFAOYSA-N benzotriazole-1-carbonitrile Chemical compound C1=CC=C2N(C#N)N=NC2=C1 JPUHPGALPBINPO-UHFFFAOYSA-N 0.000 description 2
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000012043 crude product Substances 0.000 description 2
QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 description 2
239000003480 eluent Substances 0.000 description 2
238000003818 flash chromatography Methods 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-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
JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-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
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
206010012289 Dementia Diseases 0.000 description 1
230000004913 activation Effects 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
229940005513 antidepressants Drugs 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
208000026106 cerebrovascular disease Diseases 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
229960004341 escitalopram Drugs 0.000 description 1
WSEQXVZVJXJVFP-FQEVSTJZSA-N escitalopram Chemical compound C1([C@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WSEQXVZVJXJVFP-FQEVSTJZSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000005187 foaming Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
238000002390 rotary evaporation Methods 0.000 description 1
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 1
229940126570 serotonin reuptake inhibitor Drugs 0.000 description 1
239000003772 serotonin uptake inhibitor Substances 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
150000003751 zinc Chemical class 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

SK336-2002A 2000-07-06 2001-07-06 Method for the preparation of citalopram SK3362002A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
PCT/EP2000/006426 WO2001002383A2 (en)	1999-07-06	2000-07-06	Process for the synthesis of citalopram
PCT/DK2001/000481 WO2002004435A1 (en)	2000-07-06	2001-07-06	Method for the preparation of citalopram

Publications (1)

Publication Number	Publication Date
SK3362002A3 true SK3362002A3 (en)	2002-08-06

Family

ID=8164018

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK336-2002A SK3362002A3 (en)	2000-07-06	2001-07-06	Method for the preparation of citalopram

Country Status (11)

Country	Link
US (1)	US20020128497A1 (is)
AU (1)	AU2001272368A1 (is)
BR (1)	BR0106976A (is)
CA (1)	CA2383963A1 (is)
CZ (1)	CZ2002832A3 (is)
EA (1)	EA200200332A1 (is)
IL (1)	IL148525A0 (is)
IS (1)	IS6293A (is)
NO (1)	NO20021118L (is)
SK (1)	SK3362002A3 (is)
WO (1)	WO2002004435A1 (is)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU759716B2 (en)	1999-04-14	2003-04-17	H. Lundbeck A/S	Method for the preparation of citalopram
IES20010157A2 (en)	2000-03-03	2002-03-06	Lundbeck & Co As H	Method for the preparation of citalopram
PL360110A1 (en)	2000-03-13	2004-09-06	H.Lundbeck A/S	Method for the preparation of citalopram
CN1427835A (zh) *	2000-03-13	2003-07-02	H·隆德贝克有限公司	5－取代的1－(4－氟苯基)－1,3－二氢异苯并呋喃的分步烷基化
NL1017500C1 (nl)	2000-03-13	2001-04-26	Lundbeck & Co As H	Werkwijze voor de bereiding van Citalopram.
TR200202155T2 (tr)	2000-03-14	2002-12-23	H. Lundbeck A/S	Sitalopramin preparasyon metodu
CZ20023406A3 (cs) *	2000-03-16	2003-01-15	H. Lundbeck A/S	Způsob výroby 5-kyano-1-(4-fluorfenyl)-1,3-dihydroisobenzofuranu
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
US20050154052A1 (en) *	2003-03-24	2005-07-14	Hetero Drugs Limited	Novel crystalline forms of (s)-citalopram oxalate

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1526331A (en) *	1976-01-14	1978-09-27	Kefalas As	Phthalanes
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

2001
- 2001-07-06 CZ CZ2002832A patent/CZ2002832A3/cs unknown
- 2001-07-06 EA EA200200332A patent/EA200200332A1/ru unknown
- 2001-07-06 WO PCT/DK2001/000481 patent/WO2002004435A1/en not_active Ceased
- 2001-07-06 SK SK336-2002A patent/SK3362002A3/sk unknown
- 2001-07-06 AU AU2001272368A patent/AU2001272368A1/en not_active Abandoned
- 2001-07-06 CA CA002383963A patent/CA2383963A1/en not_active Abandoned
- 2001-07-06 BR BR0106976-4A patent/BR0106976A/pt not_active Application Discontinuation
- 2001-07-06 IL IL14852501A patent/IL148525A0/xx unknown
2002
- 2002-03-05 IS IS6293A patent/IS6293A/is unknown
- 2002-03-06 NO NO20021118A patent/NO20021118L/no not_active Application Discontinuation
- 2002-03-06 US US10/096,149 patent/US20020128497A1/en not_active Abandoned

Also Published As

Publication number	Publication date
CA2383963A1 (en)	2002-01-17
IS6293A (is)	2002-03-05
US20020128497A1 (en)	2002-09-12
AU2001272368A1 (en)	2002-01-21
WO2002004435A1 (en)	2002-01-17
NO20021118D0 (no)	2002-03-06
BR0106976A (pt)	2002-07-23
CZ2002832A3 (cs)	2002-05-15
IL148525A0 (en)	2002-09-12
EA200200332A1 (ru)	2002-06-27
NO20021118L (no)	2002-04-24

Publication	Publication Date	Title
FI108538B (fi)	2002-02-15	Menetelmä sitalopraamin valmistamiseksi
JP3447267B2 (ja)	2003-09-16	シタロプラムの製造方法
AU738526B2 (en)	2001-09-20	Method for the preparation of citalopram
US6426422B1 (en)	2002-07-30	Method for the preparation of citalopram
SK6822000A3 (en)	2000-10-09	Obsahom a medziprodukty method for the preparation of citalopram, pharmaceutical composition containing the same and intermediates
US20030114692A1 (en)	2003-06-19	Method for the preparation of citalopram
SK3362002A3 (en)	2002-08-06	Method for the preparation of citalopram
WO2001002383A2 (en)	2001-01-11	Process for the synthesis of citalopram
KR100653141B1 (ko)	2006-12-01	시탈로프람의 제조 방법
EP1296970B1 (en)	2008-03-19	Method for the preparation of citalopram
CA2291133C (en)	2003-06-17	Method for the preparation of citalopram
KR100466463B1 (ko)	2005-01-13	시탈로프람의 제조방법
WO2005042473A1 (en)	2005-05-12	Improved process for the manufacture of citalopram hydrobromide
BG64446B1 (en)	2005-02-28	Method for the preparation of citalopram, intermediates for its materialization and antidepressive agent
HUP0003666A2 (en)	2002-06-29	Method for the preparation of citalopram and pharmaceutical compositions containing them