SK14592002A3 - Spôsob prípravy citalopramu, antidepresívny farmaceutický prostriedok s jeho obsahom a medziprodukty - Google Patents

Spôsob prípravy citalopramu, antidepresívny farmaceutický prostriedok s jeho obsahom a medziprodukty Download PDF

Info

Publication number: SK14592002A3
Authority: SK; Slovakia
Prior art keywords: cyano; compound; group; formula; citalopram
Prior art date: 2000-03-13

Application number

SK1459-2002A

Other languages

English (en)

Slovak (sk)

Inventor

Hans Petersen

Original Assignee

H. Lundbeck A/S

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.)

2000-03-13

Filing date

2001-03-07

Publication date

2003-03-04

2001-03-07 Application filed by H. Lundbeck A/S filed Critical H. Lundbeck A/S

2003-03-04 Publication of SK14592002A3 publication Critical patent/SK14592002A3/sk

Links

229960001653 citalopram Drugs 0.000 title claims abstract description 26
WSEQXVZVJXJVFP-HXUWFJFHSA-N (R)-citalopram Chemical compound C1([C@@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WSEQXVZVJXJVFP-HXUWFJFHSA-N 0.000 title claims abstract description 25
238000000034 method Methods 0.000 title claims abstract description 24
238000002360 preparation method Methods 0.000 title claims abstract description 11
150000001875 compounds Chemical class 0.000 claims abstract description 63
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 54
238000006243 chemical reaction Methods 0.000 claims abstract description 41
150000003839 salts Chemical class 0.000 claims description 15
239000002253 acid Substances 0.000 claims description 12
230000018044 dehydration Effects 0.000 claims description 10
238000006297 dehydration reaction Methods 0.000 claims description 10
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 6
230000001430 anti-depressive effect Effects 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 5
150000002118 epoxides Chemical class 0.000 claims description 3
238000005502 peroxidation Methods 0.000 claims description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
125000000217 alkyl group Chemical group 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
229910052739 hydrogen Inorganic materials 0.000 description 9
239000001257 hydrogen Substances 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 8
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
239000002904 solvent Substances 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
150000002148 esters Chemical class 0.000 description 7
-1 methylsulfinyl methide Chemical compound 0.000 description 7
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
125000003710 aryl alkyl group Chemical group 0.000 description 6
239000012024 dehydrating agents‎ Substances 0.000 description 6
229910052736 halogen Inorganic materials 0.000 description 6
150000002367 halogens Chemical class 0.000 description 6
RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 6
239000000243 solution Substances 0.000 description 6
150000001408 amides Chemical class 0.000 description 5
125000003118 aryl group Chemical group 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
239000000935 antidepressant agent Substances 0.000 description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 4
150000002431 hydrogen Chemical class 0.000 description 4
150000007522 mineralic acids Chemical class 0.000 description 4
239000007858 starting material Substances 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
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 description 3
125000003504 2-oxazolinyl group Chemical group O1C(=NCC1)* 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical group O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
239000002671 adjuvant Substances 0.000 description 3
125000003342 alkenyl group Chemical group 0.000 description 3
125000000304 alkynyl group Chemical group 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
239000002585 base Substances 0.000 description 3
230000003197 catalytic effect Effects 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
235000019439 ethyl acetate Nutrition 0.000 description 3
239000007924 injection Substances 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
OVEHNNQXLPJPPL-UHFFFAOYSA-N lithium;n-propan-2-ylpropan-2-amine Chemical compound [Li].CC(C)NC(C)C OVEHNNQXLPJPPL-UHFFFAOYSA-N 0.000 description 3
229910052763 palladium Inorganic materials 0.000 description 3
MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
QQIRAVWVGBTHMJ-UHFFFAOYSA-N [dimethyl-(trimethylsilylamino)silyl]methane;lithium Chemical compound [Li].C[Si](C)(C)N[Si](C)(C)C QQIRAVWVGBTHMJ-UHFFFAOYSA-N 0.000 description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
150000003973 alkyl amines Chemical class 0.000 description 2
125000004457 alkyl amino carbonyl group Chemical group 0.000 description 2
125000004448 alkyl carbonyl group Chemical group 0.000 description 2
239000002168 alkylating agent Substances 0.000 description 2
229940100198 alkylating agent Drugs 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 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
238000004519 manufacturing process Methods 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000000203 mixture Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 2
125000003003 spiro group Chemical group 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
239000003826 tablet Substances 0.000 description 2
125000002769 thiazolinyl group Chemical group 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 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
NYYRRBOMNHUCLB-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCCl NYYRRBOMNHUCLB-UHFFFAOYSA-N 0.000 description 1
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-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
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 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
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-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
239000002841 Lewis acid Substances 0.000 description 1
229910019093 NaOCl Inorganic materials 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-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
235000011054 acetic acid Nutrition 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
230000009435 amidation Effects 0.000 description 1
238000007112 amidation reaction Methods 0.000 description 1
125000003368 amide group Chemical group 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
229940005513 antidepressants Drugs 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
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
244000309464 bull Species 0.000 description 1
125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
208000026106 cerebrovascular disease Diseases 0.000 description 1
WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000010949 copper Substances 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
238000006193 diazotization reaction Methods 0.000 description 1
229940043279 diisopropylamine Drugs 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
FFHWGQQFANVOHV-UHFFFAOYSA-N dimethyldioxirane Chemical compound CC1(C)OO1 FFHWGQQFANVOHV-UHFFFAOYSA-N 0.000 description 1
239000000975 dye Substances 0.000 description 1
239000003480 eluent Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
238000011049 filling Methods 0.000 description 1
239000012458 free base 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
150000004820 halides Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000001072 heteroaryl group Chemical group 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 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
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
150000007517 lewis acids Chemical class 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
244000005700 microbiome Species 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000002950 monocyclic group Chemical group 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
125000001624 naphthyl group Chemical group 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000004967 organic peroxy acids Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
150000002923 oximes Chemical class 0.000 description 1
IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
230000000379 polymerizing effect Effects 0.000 description 1
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002243 precursor Chemical group 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
230000002040 relaxant effect Effects 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
238000007363 ring formation reaction 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
238000000926 separation method 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
238000010898 silica gel chromatography Methods 0.000 description 1
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 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
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
229960000278 theophylline Drugs 0.000 description 1
CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical group C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
- A61K31/343—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide condensed with a carbocyclic ring, e.g. coumaran, bufuralol, befunolol, clobenfurol, amiodarone
- 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

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Neurology (AREA)
Pain & Pain Management (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Neurosurgery (AREA)
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Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Psychiatry (AREA)
General Chemical & Material Sciences (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Steroid Compounds (AREA)
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SK1459-2002A 2000-03-13 2001-03-07 Spôsob prípravy citalopramu, antidepresívny farmaceutický prostriedok s jeho obsahom a medziprodukty SK14592002A3 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DKPA200000404		2000-03-13
PCT/DK2001/000149 WO2001068628A1 (en)	2000-03-13	2001-03-07	Method for the preparation of citalopram

Publications (1)

Publication Number	Publication Date
SK14592002A3 true SK14592002A3 (sk)	2003-03-04

Family

ID=8159323

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1459-2002A SK14592002A3 (sk)	2000-03-13	2001-03-07	Spôsob prípravy citalopramu, antidepresívny farmaceutický prostriedok s jeho obsahom a medziprodukty

Country Status (31)

Country	Link
US (1)	US6717000B2 (de)
EP (1)	EP1265880B1 (de)
JP (1)	JP2003527384A (de)
KR (1)	KR20020080471A (de)
CN (1)	CN1423644A (de)
AR (1)	AR029893A1 (de)
AT (1)	ATE282031T1 (de)
AU (1)	AU3920301A (de)
BE (1)	BE1011598A6 (de)
BG (1)	BG107048A (de)
BR (1)	BR0109267A (de)
CA (1)	CA2402386A1 (de)
CZ (1)	CZ20023383A3 (de)
DE (1)	DE60107061D1 (de)
EA (1)	EA200200971A1 (de)
FR (1)	FR2806085B1 (de)
HR (1)	HRP20020741A2 (de)
HU (1)	HUP0300180A2 (de)
IE (1)	IES20010206A2 (de)
IL (1)	IL151489A0 (de)
IS (1)	IS6528A (de)
IT (1)	ITMI20010487A1 (de)
MX (1)	MXPA02008872A (de)
NL (1)	NL1017500C1 (de)
NO (1)	NO20024214L (de)
NZ (1)	NZ521202A (de)
PL (1)	PL360108A1 (de)
SK (1)	SK14592002A3 (de)
TR (1)	TR200202167T2 (de)
WO (1)	WO2001068628A1 (de)
ZA (1)	ZA200206898B (de)

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IL145615A0 (en) *	1999-04-14	2002-06-30	Lundbeck & Co As H	Method for the preparation of citalopram
IES20010157A2 (en)	2000-03-03	2002-03-06	Lundbeck & Co As H	Method for the preparation of citalopram
BR0109364A (pt)	2000-03-13	2002-12-24	Lundbeck & Co As H	Métodos para fabricação de citalopram através de alquilação escalonada de 5-substituìda 1- (4-fluorofenil) - 1,3- diidroisobenzofuranos e citalopram
SK14602002A3 (sk)	2000-03-13	2003-02-04	H. Lundbeck A/S	Spôsob výroby citalopramu a medziprodukty
IL151488A0 (en)	2000-03-14	2003-04-10	Lundbeck & Co As H	Method for the preparation of citalopram
AR032455A1 (es)	2000-05-12	2003-11-12	Lundbeck & Co As H	Metodo para la preparacion de citalopram, un intermediario empleado en el metodo, un metodo para la preparacion del intermediario empleado en el metodo y composicion farmaceutica antidepresiva
AU2003223105A1 (en) *	2003-03-24	2004-10-18	Hetero Drugs Limited	Novel crystalline forms of (s)-citalopram oxalate
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

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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
SK14602002A3 (sk)	2000-03-13	2003-02-04	H. Lundbeck A/S	Spôsob výroby citalopramu a medziprodukty
GB2357762B (en)	2000-03-13	2002-01-30	Lundbeck & Co As H	Crystalline base of citalopram
BR0109364A (pt)	2000-03-13	2002-12-24	Lundbeck & Co As H	Métodos para fabricação de citalopram através de alquilação escalonada de 5-substituìda 1- (4-fluorofenil) - 1,3- diidroisobenzofuranos e citalopram
IL151488A0 (en)	2000-03-14	2003-04-10	Lundbeck & Co As H	Method for the preparation of citalopram
TR200202168T2 (tr)	2000-03-16	2002-12-23	H. Lundbeck A/S	5-Siyano-1-(4-Florofenil)-1,3-Dihidroizobenzofuranların preparasyon metodu
AR032455A1 (es)	2000-05-12	2003-11-12	Lundbeck & Co As H	Metodo para la preparacion de citalopram, un intermediario empleado en el metodo, un metodo para la preparacion del intermediario empleado en el metodo y composicion farmaceutica antidepresiva
SK3362002A3 (en)	2000-07-06	2002-08-06	Lundbeck & Co As H	Method for the preparation of citalopram
IL144816A (en)	2000-08-18	2005-09-25	Lundbeck & Co As H	Method for the preparation of citalopram
TR200201166T1 (tr)	2000-12-22	2002-10-21	H.Lundbecks A/S	Saf sitalopram hazırlanması için yöntem
JP2003519121A (ja)	2000-12-28	2003-06-17	ハー・ルンドベック・アクチエゼルスカベット	純粋なシタロプラムの製造方法

2001
- 2001-03-05 NL NL1017500A patent/NL1017500C1/nl not_active IP Right Cessation
- 2001-03-05 IE IE20010206A patent/IES20010206A2/en not_active IP Right Cessation
- 2001-03-07 HR HR20020741A patent/HRP20020741A2/hr not_active Application Discontinuation
- 2001-03-07 JP JP2001567720A patent/JP2003527384A/ja not_active Withdrawn
- 2001-03-07 DE DE60107061T patent/DE60107061D1/de not_active Expired - Lifetime
- 2001-03-07 CZ CZ20023383A patent/CZ20023383A3/cs unknown
- 2001-03-07 CA CA002402386A patent/CA2402386A1/en not_active Abandoned
- 2001-03-07 BR BR0109267-7A patent/BR0109267A/pt not_active IP Right Cessation
- 2001-03-07 EP EP01913728A patent/EP1265880B1/de not_active Expired - Lifetime
- 2001-03-07 AT AT01913728T patent/ATE282031T1/de not_active IP Right Cessation
- 2001-03-07 AR ARP010101064A patent/AR029893A1/es unknown
- 2001-03-07 CN CN01806481A patent/CN1423644A/zh active Pending
- 2001-03-07 IL IL15148901A patent/IL151489A0/xx unknown
- 2001-03-07 HU HU0300180A patent/HUP0300180A2/hu unknown
- 2001-03-07 NZ NZ521202A patent/NZ521202A/en unknown
- 2001-03-07 WO PCT/DK2001/000149 patent/WO2001068628A1/en not_active Ceased
- 2001-03-07 AU AU39203/01A patent/AU3920301A/en not_active Abandoned
- 2001-03-07 TR TR2002/02167T patent/TR200202167T2/xx unknown
- 2001-03-07 SK SK1459-2002A patent/SK14592002A3/sk unknown
- 2001-03-07 EA EA200200971A patent/EA200200971A1/ru unknown
- 2001-03-07 PL PL36010801A patent/PL360108A1/xx not_active Application Discontinuation
- 2001-03-07 MX MXPA02008872A patent/MXPA02008872A/es unknown
- 2001-03-07 KR KR1020027011671A patent/KR20020080471A/ko not_active Withdrawn
- 2001-03-08 IT IT2001MI000487A patent/ITMI20010487A1/it unknown
- 2001-03-09 FR FR0103245A patent/FR2806085B1/fr not_active Expired - Fee Related
- 2001-03-13 BE BE2001/0159A patent/BE1011598A6/fr not_active IP Right Cessation
2002
- 2002-08-27 IS IS6528A patent/IS6528A/is unknown
- 2002-08-28 ZA ZA200206898A patent/ZA200206898B/en unknown
- 2002-09-02 BG BG107048A patent/BG107048A/xx unknown
- 2002-09-04 NO NO20024214A patent/NO20024214L/no not_active Application Discontinuation
- 2002-09-09 US US10/238,843 patent/US6717000B2/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
MXPA02008872A (es)	2003-02-10
US20030069304A1 (en)	2003-04-10
ITMI20010487A1 (it)	2002-09-08
FR2806085B1 (fr)	2005-02-25
AU3920301A (en)	2001-09-24
BG107048A (en)	2003-05-30
EP1265880B1 (de)	2004-11-10
EA200200971A1 (ru)	2003-02-27
CA2402386A1 (en)	2001-09-20
NO20024214L (no)	2002-10-31
NO20024214D0 (no)	2002-09-04
NL1017500C1 (nl)	2001-04-26
HRP20020741A2 (en)	2003-12-31
IL151489A0 (en)	2003-04-10
WO2001068628A1 (en)	2001-09-20
BE1011598A6 (fr)	2001-07-03
KR20020080471A (ko)	2002-10-23
US6717000B2 (en)	2004-04-06
TR200202167T2 (tr)	2002-12-23
CZ20023383A3 (cs)	2003-01-15
AR029893A1 (es)	2003-07-23
EP1265880A1 (de)	2002-12-18
HUP0300180A2 (en)	2003-05-28
BR0109267A (pt)	2002-12-17
ZA200206898B (en)	2004-04-20
DE60107061D1 (de)	2004-12-16
PL360108A1 (en)	2004-09-06
NZ521202A (en)	2004-11-26
FR2806085A1 (fr)	2001-09-14
CN1423644A (zh)	2003-06-11
IES20010206A2 (en)	2002-03-06
ATE282031T1 (de)	2004-11-15
IS6528A (is)	2002-08-27
JP2003527384A (ja)	2003-09-16

Publication	Publication Date	Title
NO312031B1 (no)	2002-03-04	Krystallin base av citalopram
SK285813B6 (sk)	2007-08-02	Spôsob prípravy citalopramu, farmaceutický prostriedok s obsahom citalopramu a medziprodukt
SK18482001A3 (sk)	2002-05-09	Spôsob výroby citalopramu
SK14812002A3 (sk)	2003-02-04	Spôsob prípravy 5-kyano-1-(4-fluórfenyl)-1,3-dihydrobenzofuránov a antidepresívny farmaceutický prostriedok
SK14152002A3 (sk)	2003-03-04	Spôsob prípravy citalopramu a antidepresívny farmaceutický prostriedok s obsahom citalopramu
US6762308B2 (en)	2004-07-13	Method for the preparation of citalopram
US6806376B2 (en)	2004-10-19	Method for the preparation of citalopram
SK17542002A3 (sk)	2003-04-01	Spôsob prípravy citalopramu, medziprodukt a antidepresívny farmaceutický prostriedok s obsahom citalopramu
SK14522002A3 (sk)	2003-03-04	Spôsob prípravy citalopramu a citalopram pripravený týmto spôsobom
US6717000B2 (en)	2004-04-06	Method for the preparation of citalopram
HK1054553A (en)	2003-12-05	Method for the preparation of citalopram