IL147339A - Preparation of crystalline base of citalopram and hydrochloride or hydrobromide salts - Google Patents

Preparation of crystalline base of citalopram and hydrochloride or hydrobromide salts

Info

Publication number: IL147339A
Authority: IL; Israel
Prior art keywords: citalopram; salt; base; crude; hydrochloride
Prior art date: 2000-03-13

Application number

IL14733901A

Other languages

English (en)

Other versions

IL147339A0 (en

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

2001-02-28

Publication date

2004-09-27

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=IL147339(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2001-02-28 Application filed by Lundbeck & Co As H filed Critical Lundbeck & Co As H

2001-02-28 Priority to IL15807201A priority Critical patent/IL158072A0/xx

2002-08-14 Publication of IL147339A0 publication Critical patent/IL147339A0/xx

2004-09-27 Publication of IL147339A publication Critical patent/IL147339A/en

Links

229960001653 citalopram Drugs 0.000 title claims abstract description 106
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 105
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 title claims description 22
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 title claims description 14
238000002360 preparation method Methods 0.000 title description 8
150000003839 salts Chemical class 0.000 claims abstract description 48
238000000034 method Methods 0.000 claims abstract description 35
239000002904 solvent Substances 0.000 claims abstract description 19
238000004519 manufacturing process Methods 0.000 claims abstract description 10
239000000203 mixture Substances 0.000 claims description 35
238000006243 chemical reaction Methods 0.000 claims description 33
150000001875 compounds Chemical class 0.000 claims description 14
125000000217 alkyl group Chemical group 0.000 claims description 10
238000000746 purification Methods 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
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 7
229910052736 halogen Inorganic materials 0.000 claims description 7
150000002367 halogens Chemical class 0.000 claims description 7
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical group N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 6
239000012535 impurity Substances 0.000 claims description 6
125000003710 aryl alkyl group Chemical group 0.000 claims description 5
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 4
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
229910021653 sulphate ion Inorganic materials 0.000 claims description 3
229910019142 PO4 Inorganic materials 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
230000001376 precipitating effect Effects 0.000 claims description 2
125000003107 substituted aryl group Chemical group 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
150000002823 nitrates Chemical class 0.000 claims 1
UXQPRXPNOJXOQO-UHFFFAOYSA-N sulfuric acid;hydrobromide Chemical compound Br.OS(O)(=O)=O UXQPRXPNOJXOQO-UHFFFAOYSA-N 0.000 claims 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
239000002585 base Substances 0.000 description 46
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 14
239000003054 catalyst Substances 0.000 description 14
239000003826 tablet Substances 0.000 description 14
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 10
125000004093 cyano group Chemical group *C#N 0.000 description 9
239000012458 free base Substances 0.000 description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
239000008187 granular material Substances 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
239000002253 acid Substances 0.000 description 7
239000002671 adjuvant Substances 0.000 description 7
150000002148 esters Chemical group 0.000 description 7
239000012071 phase Substances 0.000 description 7
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 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
239000011701 zinc Substances 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
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
230000003197 catalytic effect Effects 0.000 description 6
238000001816 cooling Methods 0.000 description 6
239000003085 diluting agent Substances 0.000 description 6
238000009472 formulation Methods 0.000 description 6
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
-1 5-thiazolinyl group Chemical group 0.000 description 5
229910006124 SOCl2 Inorganic materials 0.000 description 5
150000001408 amides Chemical group 0.000 description 5
125000003118 aryl group Chemical group 0.000 description 5
239000002775 capsule Substances 0.000 description 5
239000000543 intermediate Substances 0.000 description 5
239000008194 pharmaceutical composition Substances 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
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-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
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
239000000935 antidepressant agent Substances 0.000 description 4
239000012024 dehydrating agents‎ Substances 0.000 description 4
238000005469 granulation Methods 0.000 description 4
230000003179 granulation Effects 0.000 description 4
150000002825 nitriles Chemical group 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
229960001866 silicon dioxide Drugs 0.000 description 4
MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 4
239000001117 sulphuric acid Substances 0.000 description 4
235000011149 sulphuric acid Nutrition 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-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
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 3
229910019213 POCl3 Inorganic materials 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
239000000654 additive Substances 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
239000003795 chemical substances by application Substances 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
238000002425 crystallisation Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
229910052763 palladium Inorganic materials 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
239000000243 solution Substances 0.000 description 3
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 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical compound [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 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
230000000996 additive effect Effects 0.000 description 2
150000003973 alkyl amines Chemical class 0.000 description 2
230000001430 anti-depressive effect Effects 0.000 description 2
229940005513 antidepressants Drugs 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
239000007795 chemical reaction product Substances 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
238000007906 compression Methods 0.000 description 2
230000006835 compression Effects 0.000 description 2
230000018044 dehydration Effects 0.000 description 2
238000006297 dehydration reaction Methods 0.000 description 2
238000007907 direct compression Methods 0.000 description 2
229940093499 ethyl acetate Drugs 0.000 description 2
235000019439 ethyl acetate Nutrition 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
238000011065 in-situ storage Methods 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 2
239000000314 lubricant Substances 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
239000000155 melt Substances 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
WXHIJDCHNDBCNY-UHFFFAOYSA-N palladium dihydride Chemical compound [PdH2] WXHIJDCHNDBCNY-UHFFFAOYSA-N 0.000 description 2
239000003755 preservative agent Substances 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
238000001953 recrystallisation Methods 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
239000008096 xylene Substances 0.000 description 2
229910052725 zinc Inorganic materials 0.000 description 2
WIHMBLDNRMIGDW-UHFFFAOYSA-N 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-3h-2-benzofuran-5-carbonitrile;hydron;bromide Chemical compound [Br-].O1CC2=CC(C#N)=CC=C2C1(CCC[NH+](C)C)C1=CC=C(F)C=C1 WIHMBLDNRMIGDW-UHFFFAOYSA-N 0.000 description 1
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
206010012289 Dementia Diseases 0.000 description 1
239000001828 Gelatine Substances 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
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
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
229910002651 NO3 Inorganic materials 0.000 description 1
229910021585 Nickel(II) bromide Inorganic materials 0.000 description 1
229910021586 Nickel(II) chloride Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
XAJMJYPAJNLKIS-UHFFFAOYSA-N [5-(4-bromophenyl)furan-2-yl]methanamine Chemical compound O1C(CN)=CC=C1C1=CC=C(Br)C=C1 XAJMJYPAJNLKIS-UHFFFAOYSA-N 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
239000003963 antioxidant agent Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
208000026106 cerebrovascular disease Diseases 0.000 description 1
238000006757 chemical reactions by type Methods 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 description 1
229960000584 citalopram hydrobromide Drugs 0.000 description 1
238000004040 coloring Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
238000007333 cyanation reaction Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
229940035423 ethyl ether Drugs 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
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000011049 filling Methods 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000001072 heteroaryl group Chemical group 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
239000002608 ionic liquid Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000008101 lactose Substances 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
239000003446 ligand Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
238000007909 melt granulation Methods 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
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
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229910052759 nickel Inorganic materials 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
229910000069 nitrogen hydride Inorganic materials 0.000 description 1
239000012454 non-polar solvent Substances 0.000 description 1
229940099990 ogen Drugs 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
UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 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
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000001556 precipitation Methods 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
239000008213 purified water Substances 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
229940076279 serotonin Drugs 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000000547 substituted alkyl 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
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
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
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
238000005550 wet granulation Methods 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

Landscapes

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)
Compositions Of Macromolecular Compounds (AREA)
Laminated Bodies (AREA)
Medicinal Preparation (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Silicates, Zeolites, And Molecular Sieves (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Manufacture Of Macromolecular Shaped Articles (AREA)
Plural Heterocyclic Compounds (AREA)

IL14733901A 2000-03-13 2001-02-28 Preparation of crystalline base of citalopram and hydrochloride or hydrobromide salts IL147339A (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
IL15807201A IL158072A0 (en)	2000-03-13	2001-02-28	Crystalline base of citalopram

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DKPA200000402		2000-03-13
DKPCT/DK00/00183		2000-04-13
PCT/DK2001/000137 WO2001068627A1 (en)	2000-03-13	2001-02-28	Crystalline base of citalopram

Publications (2)

Publication Number	Publication Date
IL147339A0 IL147339A0 (en)	2002-08-14
IL147339A true IL147339A (en)	2004-09-27

Family

ID=8159320

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
IL14733901A IL147339A (en)	2000-03-13	2001-02-28	Preparation of crystalline base of citalopram and hydrochloride or hydrobromide salts
IL15807201A IL158072A0 (en)	2000-03-13	2001-02-28	Crystalline base of citalopram

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
IL15807201A IL158072A0 (en)	2000-03-13	2001-02-28	Crystalline base of citalopram

Country Status (41)

Country	Link
US (7)	US20010031784A1 (de)
EP (2)	EP1169314B2 (de)
JP (1)	JP2003527383A (de)
KR (1)	KR20020080486A (de)
CN (2)	CN1258530C (de)
AR (1)	AR029811A1 (de)
AT (3)	ATE223396T1 (de)
AU (2)	AU746664B2 (de)
BE (1)	BE1013210A3 (de)
BG (1)	BG107065A (de)
BR (1)	BR0109373A (de)
CA (2)	CA2360287C (de)
CH (2)	CH691537A5 (de)
CZ (1)	CZ292077B6 (de)
DE (7)	DE20007303U1 (de)
DK (3)	DK173903B1 (de)
EA (1)	EA200200972A1 (de)
ES (3)	ES2173054T3 (de)
FI (2)	FI20010156A0 (de)
FR (1)	FR2806086B1 (de)
GB (2)	GB2357762B (de)
GR (1)	GR1003796B (de)
HR (1)	HRP20020756A2 (de)
HU (3)	HU0001581D0 (de)
IE (1)	IES20010109A2 (de)
IL (2)	IL147339A (de)
IS (1)	IS5841A (de)
IT (2)	IT1319645B1 (de)
MX (1)	MXPA02008793A (de)
NL (2)	NL1016435C1 (de)
NO (2)	NO312031B1 (de)
PL (1)	PL360158A1 (de)
PT (2)	PT1169314E (de)
SE (2)	SE517136C2 (de)
SI (2)	SI1227088T1 (de)
SK (1)	SK285528B6 (de)
TR (1)	TR200202185T2 (de)
UA (1)	UA74360C2 (de)
WO (1)	WO2001068627A1 (de)
YU (1)	YU68802A (de)
ZA (1)	ZA200207148B (de)

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GB0206708D0 (en) *	2002-03-21	2002-05-01	Cipla Ltd	Pharmaceutical salts
US6812355B2 (en)	2002-10-22	2004-11-02	Sekhsaria Chemicals Limited	Process for the manufacture of citalopram hydrobromide from 5-bromophthalide
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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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EP1901714A2 (de) *	2005-05-20	2008-03-26	Aurobindo Pharma Limited	Pharmazeutische dosierformen mit escitalopram in granulatform
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US7834201B2 (en)	2005-06-22	2010-11-16	H. Lundbeck A/S	Crystalline base of escitalopram and orodispersible tablets comprising escitalopram base
RU2408368C2 (ru)	2005-06-27	2011-01-10	Биовэйл Лэборэториз Интернэшнл С.Р.Л.	Препараты соли бупропиона с модифицированным высвобождением
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JP5281195B2 (ja)	2009-05-14	2013-09-04	コヴィディエンリミテッドパートナーシップ	簡単に清掃され得るアテレクトミー用カテーテルおよび使用の方法
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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
- 2000-10-18 NL NL1016435A patent/NL1016435C1/nl not_active IP Right Cessation
- 2000-11-09 IT IT2000MI002425A patent/IT1319645B1/it active
- 2000-12-05 US US09/730,490 patent/US20010031784A1/en not_active Abandoned
2001
- 2001-01-25 FI FI20010156A patent/FI20010156A0/fi unknown
- 2001-01-26 HU HU0100450A patent/HU0100450D0/hu unknown
- 2001-02-05 GB GBGB0102797.8A patent/GB0102797D0/en not_active Ceased
- 2001-02-05 IS IS5841A patent/IS5841A/is unknown
- 2001-02-05 HU HU0100531A patent/HUP0100531A3/hu unknown
- 2001-02-05 DK DK200100183A patent/DK173903B1/da not_active IP Right Cessation
- 2001-02-06 NO NO20010619A patent/NO312031B1/no active IP Right Review Request
- 2001-02-07 IE IE20010109A patent/IES20010109A2/en not_active IP Right Cessation
- 2001-02-07 FI FI20010225A patent/FI109022B/fi active
- 2001-02-12 GR GR20010100074A patent/GR1003796B/el unknown
- 2001-02-20 DE DE10108042A patent/DE10108042A1/de not_active Withdrawn
- 2001-02-20 DE DE20121240U patent/DE20121240U1/de not_active Ceased
- 2001-02-20 DE DE10164687A patent/DE10164687B4/de not_active Revoked
- 2001-02-21 NL NL1017413A patent/NL1017413C1/nl not_active IP Right Cessation
- 2001-02-21 FR FR0102340A patent/FR2806086B1/fr not_active Expired - Fee Related
- 2001-02-22 CH CH00580/01A patent/CH691537A5/de not_active IP Right Cessation
- 2001-02-22 CH CH00321/01A patent/CH691477A5/de not_active IP Right Cessation
- 2001-02-28 PT PT01909568T patent/PT1169314E/pt unknown
- 2001-02-28 DK DK02009350T patent/DK1227088T3/da active
- 2001-02-28 SK SK1313-2002A patent/SK285528B6/sk unknown
- 2001-02-28 DK DK01909568T patent/DK1169314T3/da active
- 2001-02-28 EP EP01909568A patent/EP1169314B2/de not_active Expired - Lifetime
- 2001-02-28 CA CA002360287A patent/CA2360287C/en not_active Expired - Lifetime
- 2001-02-28 EP EP02009350A patent/EP1227088B1/de not_active Revoked
- 2001-02-28 JP JP2001567719A patent/JP2003527383A/ja active Pending
- 2001-02-28 IT IT2001MI000406A patent/ITMI20010406A1/it unknown
- 2001-02-28 AR ARP010100934A patent/AR029811A1/es unknown
- 2001-02-28 WO PCT/DK2001/000137 patent/WO2001068627A1/en not_active Ceased
- 2001-02-28 AT AT01909568T patent/ATE223396T1/de not_active IP Right Cessation
- 2001-02-28 BE BE2001/0136A patent/BE1013210A3/fr not_active IP Right Cessation
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- 2001-02-28 MX MXPA02008793A patent/MXPA02008793A/es active IP Right Grant
- 2001-02-28 SI SI200130031T patent/SI1227088T1/xx unknown
- 2001-02-28 YU YU68802A patent/YU68802A/sh unknown
- 2001-02-28 CN CNB018093418A patent/CN1258530C/zh not_active Expired - Fee Related
- 2001-02-28 DE DE60100022T patent/DE60100022T3/de not_active Expired - Fee Related
- 2001-02-28 CN CNA2005100091603A patent/CN1680350A/zh active Pending
- 2001-02-28 IL IL14733901A patent/IL147339A/en not_active IP Right Cessation
- 2001-02-28 DE DE60100786T patent/DE60100786T2/de not_active Revoked
- 2001-02-28 EA EA200200972A patent/EA200200972A1/ru unknown
- 2001-02-28 HR HRP20020756 patent/HRP20020756A2/hr not_active Application Discontinuation
- 2001-02-28 SI SI200130001T patent/SI1169314T2/sl unknown
- 2001-02-28 AT AT02009350T patent/ATE250050T1/de not_active IP Right Cessation
- 2001-02-28 CA CA002411732A patent/CA2411732A1/en not_active Abandoned
- 2001-02-28 PL PL36015801A patent/PL360158A1/xx not_active Application Discontinuation
- 2001-02-28 KR KR1020027012048A patent/KR20020080486A/ko not_active Ceased
- 2001-02-28 AU AU37252/01A patent/AU746664B2/en not_active Ceased
- 2001-02-28 PT PT02009350T patent/PT1227088E/pt unknown
- 2001-02-28 TR TR2002/02185T patent/TR200202185T2/xx unknown
- 2001-02-28 BR BR0109373-8A patent/BR0109373A/pt not_active IP Right Cessation
- 2001-02-28 ES ES02009350T patent/ES2180471T3/es not_active Expired - Lifetime
- 2001-02-28 DE DE1227088T patent/DE1227088T1/de active Pending
- 2001-02-28 UA UA2002097314A patent/UA74360C2/uk unknown
- 2001-02-28 IL IL15807201A patent/IL158072A0/xx unknown
- 2001-03-05 CZ CZ2001808A patent/CZ292077B6/cs not_active IP Right Cessation
- 2001-03-07 AT AT0016601U patent/AT4364U1/de unknown
- 2001-03-09 ES ES200100548A patent/ES2159491B1/es not_active Expired - Fee Related
- 2001-07-26 AU AU2001100197A patent/AU2001100197B4/en not_active Expired
- 2001-09-14 SE SE0103046A patent/SE517136C2/sv not_active IP Right Cessation
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 US11/090,336 patent/US20050165092A1/en not_active Abandoned
- 2005-03-24 US US11/090,337 patent/US20050165244A1/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
SK13132002A3 (sk)	2003-01-09
AR029811A1 (es)	2003-07-16
CH691537A5 (de)	2001-08-15
GB0105982D0 (en)	2001-05-02
ITMI20002425A1 (it)	2002-05-09
BR0109373A (pt)	2002-12-24
GB0102797D0 (en)	2001-03-21
AU2001100197B4 (en)	2001-12-06
EP1169314B1 (de)	2002-09-04
CZ292077B6 (cs)	2003-07-16
SE0103046D0 (sv)	2001-09-14
SE0200730L (sv)	2002-08-29
ES2159491B1 (es)	2002-05-01
DE60100022D1 (de)	2002-10-10
CA2360287A1 (en)	2001-09-20
KR20020080486A (ko)	2002-10-23
NL1017413C1 (nl)	2001-09-13
ZA200207148B (en)	2003-04-23
EP1169314A1 (de)	2002-01-09
HK1054750A1 (en)	2003-12-12
SI1169314T1 (en)	2002-12-31
US20060247451A1 (en)	2006-11-02
IL147339A0 (en)	2002-08-14
FR2806086B1 (fr)	2003-05-09
ES2159491A1 (es)	2001-10-01
EP1227088A1 (de)	2002-07-31
DE10164687B4 (de)	2006-04-27
SK285528B6 (sk)	2007-03-01
US20050165244A1 (en)	2005-07-28
SE526022C2 (sv)	2005-06-14
MXPA02008793A (es)	2003-02-12
DK1169314T3 (da)	2002-10-14
CA2360287C (en)	2003-09-09
DE20007303U1 (de)	2000-07-27
US20040132808A1 (en)	2004-07-08
US20010031784A1 (en)	2001-10-18
DE60100022T2 (de)	2003-03-06
CN1680350A (zh)	2005-10-12
FI20010225L (fi)	2001-09-14
ES2173054T3 (es)	2002-12-16
NO312031B1 (no)	2002-03-04
SE517136C2 (sv)	2002-04-16
BG107065A (bg)	2003-05-30
GB2357762A (en)	2001-07-04
EA200200972A1 (ru)	2003-02-27
JP2003527383A (ja)	2003-09-16
EP1169314B2 (de)	2011-06-01
AT4364U1 (de)	2001-06-25
DE60100786T2 (de)	2004-07-15
FI109022B (fi)	2002-05-15
CH691477A5 (de)	2001-07-31
FR2806086A1 (fr)	2001-09-14
PL360158A1 (en)	2004-09-06
YU68802A (sh)	2005-11-28
NO20010619D0 (no)	2001-02-06
GR1003796B (el)	2002-02-08
IS5841A (is)	2001-09-14
HRP20020756A2 (en)	2004-12-31
NL1016435C1 (nl)	2000-11-06
ES2180471T3 (es)	2004-05-01
ES2180471T1 (es)	2003-02-16
SI1227088T1 (en)	2003-12-31
IES20010109A2 (en)	2002-02-20
NO20020356D0 (no)	2002-01-23
BE1013210A3 (fr)	2001-10-02
CZ2001808A3 (cs)	2002-01-16
NO315851B1 (no)	2003-11-03
WO2001068627A1 (en)	2001-09-20
DE1227088T1 (de)	2003-02-06
DK173903B1 (da)	2002-02-11
NO20020356L (no)	2001-09-14
DE60100022T3 (de)	2011-11-17
DE20121240U1 (de)	2002-07-04
US20040167210A1 (en)	2004-08-26
FI20010156A0 (fi)	2001-01-25
HUP0100531A3 (en)	2004-04-28
AU746664B2 (en)	2002-05-02
ITMI20010406A1 (it)	2002-08-28
DK1227088T3 (da)	2003-12-22
DE10108042A1 (de)	2001-10-18
NO20010619L (no)	2001-09-14
CN1258530C (zh)	2006-06-07
AU2001100197A4 (en)	2001-09-20
ATE223396T1 (de)	2002-09-15
IT1319645B1 (it)	2003-10-23
SE0103046L (sv)	2001-11-14
DE60100786D1 (de)	2003-10-23
PT1227088E (pt)	2003-12-31
HUP0100531A2 (hu)	2002-01-28
AU3725201A (en)	2001-09-13
PT1169314E (pt)	2002-11-29
IL158072A0 (en)	2004-03-28
UA74360C2 (uk)	2005-12-15
US20050165092A1 (en)	2005-07-28
ATE250050T1 (de)	2003-10-15
HU0100531D0 (en)	2001-03-28
HU0100450D0 (en)	2001-04-28
CN1429220A (zh)	2003-07-09
HU0001581D0 (en)	2000-06-28
EP1227088B1 (de)	2003-09-17
SI1169314T2 (sl)	2011-08-31
GB2357762B (en)	2002-01-30
FI20010225A0 (fi)	2001-02-07
TR200202185T2 (tr)	2002-12-23
US20030078442A1 (en)	2003-04-24
SE0200730D0 (sv)	2002-03-12
ES2173054T1 (es)	2002-10-16
CA2411732A1 (en)	2001-09-20

Publication	Publication Date	Title
CA2360287C (en)	2003-09-09	Crystalline base of citalopram
US20060229459A1 (en)	2006-10-12	Crystalline base of citalopram
AU738526B2 (en)	2001-09-20	Method for the preparation of citalopram
US20030114692A1 (en)	2003-06-19	Method for the preparation of citalopram
US6660873B2 (en)	2003-12-09	Method for the preparation of citalopram
US20030092761A1 (en)	2003-05-15	Method for the preparation of citalopram
AU2001258239A1 (en)	2002-02-07	Method for the preparation of citalopram
CA2402386A1 (en)	2001-09-20	Method for the preparation of citalopram

Legal Events

Date	Code	Title
2005-02-20	FF	Patent granted
2005-03-20	KB	Patent renewed
2007-06-17	KB	Patent renewed
2011-12-29	MM9K	Patent not in force due to non-payment of renewal fees