DK173903B1 - Fremgangsmåde til fremstilling af krystallinsk citalopram base og rensede salte af citalopram - Google Patents

Fremgangsmåde til fremstilling af krystallinsk citalopram base og rensede salte af citalopram Download PDF

Info

Publication number: DK173903B1
Authority: DK; Denmark
Prior art keywords: citalopram; base; salt; crude mixture; crude
Prior art date: 2000-03-13

Application number

DK200100183A

Other languages

Danish (da)

English (en)

Inventor

Klaus Peter Boegesoe

Hans Petersen

Per Holm

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.)

2000-03-13

Filing date

2001-02-05

Publication date

2002-02-11

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=8159320&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=DK173903(B1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2001-02-05 Application filed by Lundbeck & Co As H filed Critical Lundbeck & Co As H

2001-02-05 Priority to HU0400868A priority Critical patent/HUP0400868A3/hu

2001-02-05 Priority to DK200100183A priority patent/DK173903B1/da

2002-02-11 Application granted granted Critical

2002-02-11 Publication of DK173903B1 publication Critical patent/DK173903B1/da

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 110
229960001653 citalopram Drugs 0.000 title claims abstract description 110
150000003839 salts Chemical class 0.000 title claims abstract description 57
238000004519 manufacturing process Methods 0.000 title claims abstract description 5
239000000203 mixture Substances 0.000 claims abstract description 55
238000000034 method Methods 0.000 claims abstract description 26
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims abstract description 15
238000006243 chemical reaction Methods 0.000 claims description 34
239000002904 solvent Substances 0.000 claims description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
238000002360 preparation method Methods 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 10
238000000746 purification Methods 0.000 claims description 10
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
239000003960 organic solvent Substances 0.000 claims description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
150000002367 halogens Chemical class 0.000 claims description 7
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 6
229910052794 bromium Inorganic materials 0.000 claims description 6
239000012535 impurity Substances 0.000 claims description 6
125000003710 aryl alkyl group Chemical group 0.000 claims description 5
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 4
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 4
238000001953 recrystallisation Methods 0.000 claims description 4
229910021653 sulphate ion Inorganic materials 0.000 claims description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
239000002244 precipitate Substances 0.000 claims description 3
238000001556 precipitation Methods 0.000 claims description 3
125000000547 substituted alkyl group Chemical group 0.000 claims description 3
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 3
229910019142 PO4 Inorganic materials 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
150000002823 nitrates Chemical class 0.000 claims description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
239000010452 phosphate Substances 0.000 claims description 2
101001100790 Xenopus laevis Protein quaking-A Proteins 0.000 claims 1
238000002156 mixing Methods 0.000 claims 1
230000001430 anti-depressive effect Effects 0.000 abstract description 4
238000009472 formulation Methods 0.000 abstract description 3
239000000935 antidepressant agent Substances 0.000 abstract description 2
229940005513 antidepressants Drugs 0.000 abstract 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 abstract 1
239000002585 base Substances 0.000 description 58
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 17
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 16
239000003054 catalyst Substances 0.000 description 15
150000001875 compounds Chemical class 0.000 description 13
-1 5-thiazolinyl group Chemical group 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
125000004093 cyano group Chemical group *C#N 0.000 description 9
239000011701 zinc Substances 0.000 description 9
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
239000002253 acid Substances 0.000 description 7
150000002148 esters Chemical group 0.000 description 7
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 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
125000003118 aryl group Chemical group 0.000 description 6
230000003197 catalytic effect Effects 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
150000001408 amides Chemical group 0.000 description 5
239000000543 intermediate Substances 0.000 description 5
229910052759 nickel Inorganic materials 0.000 description 5
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 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
239000002775 capsule Substances 0.000 description 4
239000012024 dehydrating agents‎ Substances 0.000 description 4
229910052763 palladium Inorganic materials 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 4
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-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
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
238000001816 cooling Methods 0.000 description 3
DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 3
239000013078 crystal Substances 0.000 description 3
239000012458 free base Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000012071 phase Substances 0.000 description 3
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 3
239000011541 reaction mixture Substances 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
UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical group C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
229910006124 SOCl2 Inorganic materials 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
150000003973 alkyl amines Chemical class 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
244000309464 bull Species 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000005261 decarburization Methods 0.000 description 2
230000018044 dehydration Effects 0.000 description 2
238000006297 dehydration reaction Methods 0.000 description 2
239000012467 final product Substances 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
229910052740 iodine Inorganic materials 0.000 description 2
150000002825 nitriles Chemical group 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
239000000047 product Substances 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
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 2
239000008096 xylene Substances 0.000 description 2
229910052725 zinc Inorganic materials 0.000 description 2
CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 1
OFOQCXWSUPHERH-UHFFFAOYSA-N 2-benzofuran hydrobromide Chemical compound C1=C(C=CC=C2)C2=CO1.Br OFOQCXWSUPHERH-UHFFFAOYSA-N 0.000 description 1
CGVBIXZVEMXIQU-UHFFFAOYSA-N 3-[1-(4-fluorophenyl)-3h-2-benzofuran-1-yl]-n,n-dimethylpropan-1-amine Chemical class O1CC2=CC=CC=C2C1(CCCN(C)C)C1=CC=C(F)C=C1 CGVBIXZVEMXIQU-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
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 1
229910021585 Nickel(II) bromide Inorganic materials 0.000 description 1
229910021586 Nickel(II) chloride Inorganic materials 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
229910019213 POCl3 Inorganic materials 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 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
239000000010 aprotic solvent Substances 0.000 description 1
238000009835 boiling Methods 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
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000007333 cyanation reaction Methods 0.000 description 1
238000004042 decolorization Methods 0.000 description 1
230000000994 depressogenic effect Effects 0.000 description 1
HRKQOINLCJTGBK-UHFFFAOYSA-N dihydroxidosulfur Chemical compound OSO HRKQOINLCJTGBK-UHFFFAOYSA-N 0.000 description 1
JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
125000001207 fluorophenyl group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000001072 heteroaryl group Chemical group 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
239000002608 ionic liquid Substances 0.000 description 1
150000002500 ions Chemical class 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
150000007517 lewis acids Chemical class 0.000 description 1
239000003446 ligand Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
229910052748 manganese Inorganic materials 0.000 description 1
239000011572 manganese Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000011707 mineral Substances 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
QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
IPLJNQFXJUCRNH-UHFFFAOYSA-L nickel(2+);dibromide Chemical compound [Ni+2].[Br-].[Br-] IPLJNQFXJUCRNH-UHFFFAOYSA-L 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012454 non-polar solvent Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000002923 oximes Chemical class 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-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
239000002243 precursor Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
235000010288 sodium nitrite Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
229910052717 sulfur Inorganic materials 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
125000003944 tolyl group Chemical group 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
150000003738 xylenes 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
- 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
- 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)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicinal Preparation (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Compositions Of Macromolecular Compounds (AREA)
Laminated Bodies (AREA)
Silicates, Zeolites, And Molecular Sieves (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Manufacture Of Macromolecular Shaped Articles (AREA)
Plural Heterocyclic Compounds (AREA)

DK200100183A 2000-03-13 2001-02-05 Fremgangsmåde til fremstilling af krystallinsk citalopram base og rensede salte af citalopram DK173903B1 (da)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
HU0400868A HUP0400868A3 (en)	2000-04-13	2001-02-05	Crystalline base of citalopram and it's hydrochloride or hydrobromide salt
DK200100183A DK173903B1 (da)	2000-03-13	2001-02-05	Fremgangsmåde til fremstilling af krystallinsk citalopram base og rensede salte af citalopram

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
DKPA200000402		2000-03-13
DK200000402		2000-03-13
DKPCT/DK00/00183		2000-04-13
DK0000183		2000-04-13
DK200100183A DK173903B1 (da)	2000-03-13	2001-02-05	Fremgangsmåde til fremstilling af krystallinsk citalopram base og rensede salte af citalopram
DK200100183		2001-02-05

Publications (1)

Publication Number	Publication Date
DK173903B1 true DK173903B1 (da)	2002-02-11

Family

ID=8159320

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
DK200100183A DK173903B1 (da)	2000-03-13	2001-02-05	Fremgangsmåde til fremstilling af krystallinsk citalopram base og rensede salte af citalopram
DK02009350T DK1227088T3 (da)	2000-03-13	2001-02-28	Krystallinsk base af citalopram og hydrochlorid- eller hydrobromidsaltet deraf
DK01909568T DK1169314T3 (da)	2000-03-13	2001-02-28	Krystallinsk base af citalopram

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
DK02009350T DK1227088T3 (da)	2000-03-13	2001-02-28	Krystallinsk base af citalopram og hydrochlorid- eller hydrobromidsaltet deraf
DK01909568T DK1169314T3 (da)	2000-03-13	2001-02-28	Krystallinsk base af citalopram

Country Status (41)

Country	Link
US (7)	US20010031784A1 (fr)
EP (2)	EP1169314B2 (fr)
JP (1)	JP2003527383A (fr)
KR (1)	KR20020080486A (fr)
CN (2)	CN1258530C (fr)
AR (1)	AR029811A1 (fr)
AT (3)	ATE250050T1 (fr)
AU (2)	AU746664B2 (fr)
BE (1)	BE1013210A3 (fr)
BG (1)	BG107065A (fr)
BR (1)	BR0109373A (fr)
CA (2)	CA2411732A1 (fr)
CH (2)	CH691537A5 (fr)
CZ (1)	CZ292077B6 (fr)
DE (7)	DE20007303U1 (fr)
DK (3)	DK173903B1 (fr)
EA (1)	EA200200972A1 (fr)
ES (3)	ES2173054T3 (fr)
FI (2)	FI20010156A0 (fr)
FR (1)	FR2806086B1 (fr)
GB (2)	GB2357762B (fr)
GR (1)	GR1003796B (fr)
HR (1)	HRP20020756A2 (fr)
HU (3)	HU0001581D0 (fr)
IE (1)	IES20010109A2 (fr)
IL (2)	IL147339A (fr)
IS (1)	IS5841A (fr)
IT (2)	IT1319645B1 (fr)
MX (1)	MXPA02008793A (fr)
NL (2)	NL1016435C1 (fr)
NO (2)	NO312031B1 (fr)
PL (1)	PL360158A1 (fr)
PT (2)	PT1169314E (fr)
SE (2)	SE517136C2 (fr)
SI (2)	SI1227088T1 (fr)
SK (1)	SK285528B6 (fr)
TR (1)	TR200202185T2 (fr)
UA (1)	UA74360C2 (fr)
WO (1)	WO2001068627A1 (fr)
YU (1)	YU68802A (fr)
ZA (1)	ZA200207148B (fr)

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2000
- 2000-04-13 GB GB0105982A patent/GB2357762B/en not_active Expired - Fee Related
- 2000-04-18 HU HU0001581A patent/HU0001581D0/hu unknown
- 2000-04-20 DE DE20007303U patent/DE20007303U1/de not_active Ceased
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2001
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- 2001-02-28 PT PT01909568T patent/PT1169314E/pt unknown
- 2001-02-28 UA UA2002097314A patent/UA74360C2/uk unknown
- 2001-02-28 IT IT2001MI000406A patent/ITMI20010406A1/it unknown
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- 2001-02-28 SI SI200130031T patent/SI1227088T1/xx unknown
- 2001-02-28 EP EP01909568A patent/EP1169314B2/fr not_active Expired - Lifetime
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- 2001-02-28 CA CA002411732A patent/CA2411732A1/fr not_active Abandoned
- 2001-02-28 PT PT02009350T patent/PT1227088E/pt unknown
- 2001-02-28 BE BE2001/0136A patent/BE1013210A3/fr not_active IP Right Cessation
- 2001-02-28 EP EP02009350A patent/EP1227088B1/fr not_active Revoked
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- 2001-02-28 SI SI200130001T patent/SI1169314T2/sl unknown
- 2001-02-28 CA CA002360287A patent/CA2360287C/fr not_active Expired - Lifetime
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2002
- 2002-01-23 NO NO20020356A patent/NO315851B1/no unknown
- 2002-03-12 SE SE0200730A patent/SE526022C2/sv not_active IP Right Cessation
- 2002-09-05 BG BG107065A patent/BG107065A/bg unknown
- 2002-09-05 ZA ZA200207148A patent/ZA200207148B/en unknown
- 2002-09-12 US US10/245,824 patent/US20030078442A1/en not_active Abandoned
2003
- 2003-12-19 US US10/741,553 patent/US20040132808A1/en not_active Abandoned
- 2003-12-30 US US10/750,049 patent/US20040167210A1/en not_active Abandoned
2005
- 2005-03-24 US US11/090,337 patent/US20050165244A1/en not_active Abandoned
- 2005-03-24 US US11/090,336 patent/US20050165092A1/en not_active Abandoned
2006
- 2006-06-20 US US11/425,321 patent/US20060247451A1/en not_active Abandoned

Also Published As

Publication number	Publication date
DE1227088T1 (de)	2003-02-06
EP1169314A1 (fr)	2002-01-09
CZ292077B6 (cs)	2003-07-16
HRP20020756A2 (en)	2004-12-31
ES2159491A1 (es)	2001-10-01
PT1169314E (pt)	2002-11-29
FR2806086B1 (fr)	2003-05-09
CH691537A5 (de)	2001-08-15
EA200200972A1 (ru)	2003-02-27
ES2159491B1 (es)	2002-05-01
ITMI20010406A1 (it)	2002-08-28
IL147339A (en)	2004-09-27
DE20121240U1 (de)	2002-07-04
EP1227088B1 (fr)	2003-09-17
ZA200207148B (en)	2003-04-23
SE0200730D0 (sv)	2002-03-12
SI1169314T1 (en)	2002-12-31
BG107065A (bg)	2003-05-30
DE10164687B4 (de)	2006-04-27
HU0001581D0 (en)	2000-06-28
DE60100786D1 (de)	2003-10-23
DE20007303U1 (de)	2000-07-27
MXPA02008793A (es)	2003-02-12
UA74360C2 (uk)	2005-12-15
US20050165092A1 (en)	2005-07-28
CH691477A5 (de)	2001-07-31
IL158072A0 (en)	2004-03-28
DK1227088T3 (da)	2003-12-22
IES20010109A2 (en)	2002-02-20
SE0103046L (sv)	2001-11-14
CN1429220A (zh)	2003-07-09
HU0100450D0 (en)	2001-04-28
CN1258530C (zh)	2006-06-07
IL147339A0 (en)	2002-08-14
ES2180471T1 (es)	2003-02-16
SE526022C2 (sv)	2005-06-14
SE0200730L (sv)	2002-08-29
NO312031B1 (no)	2002-03-04
GR1003796B (el)	2002-02-08
NO20020356D0 (no)	2002-01-23
FR2806086A1 (fr)	2001-09-14
US20030078442A1 (en)	2003-04-24
DE60100022T3 (de)	2011-11-17
DK1169314T3 (da)	2002-10-14
DE60100022T2 (de)	2003-03-06
AT4364U1 (de)	2001-06-25
US20050165244A1 (en)	2005-07-28
BE1013210A3 (fr)	2001-10-02
CZ2001808A3 (cs)	2002-01-16
AU746664B2 (en)	2002-05-02
AR029811A1 (es)	2003-07-16
US20040132808A1 (en)	2004-07-08
NO20010619L (no)	2001-09-14
CN1680350A (zh)	2005-10-12
GB2357762A (en)	2001-07-04
TR200202185T2 (tr)	2002-12-23
US20060247451A1 (en)	2006-11-02
CA2411732A1 (fr)	2001-09-20
SK285528B6 (sk)	2007-03-01
NL1016435C1 (nl)	2000-11-06
NO20010619D0 (no)	2001-02-06
EP1169314B1 (fr)	2002-09-04
FI109022B (fi)	2002-05-15
SI1227088T1 (en)	2003-12-31
SK13132002A3 (sk)	2003-01-09
DE60100786T2 (de)	2004-07-15
HK1054750A1 (en)	2003-12-12
FI20010156A0 (fi)	2001-01-25
BR0109373A (pt)	2002-12-24
HUP0100531A3 (en)	2004-04-28
AU2001100197B4 (en)	2001-12-06
ITMI20002425A1 (it)	2002-05-09
DE60100022D1 (de)	2002-10-10
US20010031784A1 (en)	2001-10-18
GB0105982D0 (en)	2001-05-02
ATE250050T1 (de)	2003-10-15
NL1017413C1 (nl)	2001-09-13
US20040167210A1 (en)	2004-08-26
CA2360287C (fr)	2003-09-09
KR20020080486A (ko)	2002-10-23
GB0102797D0 (en)	2001-03-21
EP1169314B2 (fr)	2011-06-01
FI20010225A0 (fi)	2001-02-07
SE0103046D0 (sv)	2001-09-14
ES2173054T3 (es)	2002-12-16
IT1319645B1 (it)	2003-10-23
DE10108042A1 (de)	2001-10-18
PT1227088E (pt)	2003-12-31
EP1227088A1 (fr)	2002-07-31
ATE223396T1 (de)	2002-09-15
AU2001100197A4 (en)	2001-09-20
JP2003527383A (ja)	2003-09-16
NO20020356L (no)	2001-09-14
FI20010225L (fi)	2001-09-14
GB2357762B (en)	2002-01-30
ES2173054T1 (es)	2002-10-16
HU0100531D0 (en)	2001-03-28
IS5841A (is)	2001-09-14
AU3725201A (en)	2001-09-13
SE517136C2 (sv)	2002-04-16
NO315851B1 (no)	2003-11-03
WO2001068627A1 (fr)	2001-09-20
HUP0100531A2 (hu)	2002-01-28
PL360158A1 (en)	2004-09-06
YU68802A (sh)	2005-11-28
SI1169314T2 (sl)	2011-08-31
ES2180471T3 (es)	2004-05-01
CA2360287A1 (fr)	2001-09-20

Legal Events

Date	Code	Title	Description
2002-02-11	B1	Patent granted (law 1993)
2002-10-28	PPF	Opposition filed
2002-12-02	PPF	Opposition filed
2003-12-29	PDQ	Request for opposition withdrawn
2004-03-08	PDQ	Request for opposition withdrawn
2005-06-13	PDQ	Request for opposition withdrawn
2021-02-06	PUP	Patent expired	Expiry date: 20210205

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NO326570B1 (no)	2009-01-12	Fremgangsmate for fremstilling av Citalopram
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EP1296970B1 (fr)	2008-03-19	Procede de preparation de citaloprame
AU2001258239A1 (en)	2002-02-07	Method for the preparation of citalopram
SK14522002A3 (sk)	2003-03-04	Spôsob prípravy citalopramu a citalopram pripravený týmto spôsobom
HUP0300180A2 (en)	2003-05-28	Method for the preparation of citalopram
JP2004529883A (ja)	2004-09-30	シタロプラムの調製方法
KR100821912B1 (ko)	2008-04-16	시탈로프람의 제조 방법
AU2006201612B2 (en)	2008-03-13	Method for the preparation of 5-cyanophthalide
BG65515B1 (bg)	2008-10-31	Метод за получаване на 5-цианофталид