HUP0300134A2 - Method for the preparation of 5-cyano-1-(4-fluorophenyl)-1,3-dihydroisobenzofurans - Google Patents
Method for the preparation of 5-cyano-1-(4-fluorophenyl)-1,3-dihydroisobenzofuransInfo
- Publication number
- HUP0300134A2 HUP0300134A2 HU0300134A HUP0300134A HUP0300134A2 HU P0300134 A2 HUP0300134 A2 HU P0300134A2 HU 0300134 A HU0300134 A HU 0300134A HU P0300134 A HUP0300134 A HU P0300134A HU P0300134 A2 HUP0300134 A2 HU P0300134A2
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- carbon atoms
- hydrogen atom
- group
- fluorophenyl
- Prior art date
Links
- YXCRMKYHFFMNPT-UHFFFAOYSA-N 1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile Chemical class C1=CC(F)=CC=C1C1C2=CC=C(C#N)C=C2CO1 YXCRMKYHFFMNPT-UHFFFAOYSA-N 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 5
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000002947 alkylene group Chemical group 0.000 abstract 2
- 125000003003 spiro group Chemical group 0.000 abstract 2
- 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 abstract 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 1
- 239000013543 active substance Substances 0.000 abstract 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 abstract 1
- 230000001430 anti-depressive effect Effects 0.000 abstract 1
- 239000000935 antidepressant agent Substances 0.000 abstract 1
- 229940005513 antidepressants Drugs 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 229960001653 citalopram Drugs 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 239000013067 intermediate product Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 239000002243 precursor Substances 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 125000004434 sulfur atom Chemical group 0.000 abstract 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/10—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- 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)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A találmány tárgya eljárás 5-ciano-1-(4-fluorfenil)-1,3-dihidroizobenzofurán előállítására, mely vegyület köztitermékkénthasznosítható a jól ismert antidepresszáns hatóanyag, a citalopram -szabatos kémiai nevén 1-[3-(dimetilamino)propil]-1-(4-fluorfenil)-1,3-dihidro-5-izobenzofuránkarbonitril - előállítására. A (II) képletű 5-ciano1-(4-fluorfenil)-1,3-dihidroizobenzofuránt a találmány értelmébenúgy állítják elő, hogy valamely (III) általános képletű vegyületet -ebben a képletben R jelentése halogénatom, CF3-(CF2)n-SO2-O- általánosképletű csoport (ebben a képletben a értéke 0 és 8 közötti egészszám), -OH-, -CHO-, -CH2OH-, -CH2NH2, -CH2NO2, -CH2Cl, -CH2Br, -CH3, -NHR1, -COOR2 vagy -CONR2R3 csoport (az utóbbi három csoportban R1jelentése hidrogénatom vagy alkilkarbonilcsoport, míg R2 és R3egymástól függetlenül hidrogénatomot vagy adott esetben szubsztituáltalkil-, aralkil- vagy arilcsoportot jelent) vagy (IV) általánosképletű csoport (ebben a képletben X jelentése oxigén- vagy kénatom;R4 és R5 egymástól függetlenül hidrogénatomot vagy 1-6 szénatomottartalmazó alkilcsoportot jelentenek vagy együtt 2-5 szénatomottartalmazó alkilénláncot alkotnak és ezáltal spiro-gyűrűt képeznek; R6jelentése hidrogénatom vagy 1-6 szénatomot tartalmazó alkilcsoport; R7jelentése hidrogénatom, 1-6 szénatomot tartalmazó alkilcsoport,karboxilcsoport vagy az utóbbi valamelyik prekurzor-csoportja; vagy R6és R7 együtt 2-5 szénatomot tartalmazó alkilénláncot alkotnak ésezáltal spiro-gyűrűt képeznek) - a (II) képletű vegyületté alakítanak. Ó
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA200000437 | 2000-03-16 | ||
| PCT/DK2001/000186 WO2001068632A1 (en) | 2000-03-16 | 2001-03-16 | Method for the preparation of 5-cyano-1-(4-fluorophenyl)-1,3-dihydroisobenzofurans |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HUP0300134A2 true HUP0300134A2 (en) | 2003-05-28 |
Family
ID=8159344
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU0300134A HUP0300134A2 (en) | 2000-03-16 | 2001-03-16 | Method for the preparation of 5-cyano-1-(4-fluorophenyl)-1,3-dihydroisobenzofurans |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US20030060640A1 (hu) |
| EP (1) | EP1274699A1 (hu) |
| JP (1) | JP2003527388A (hu) |
| KR (1) | KR20020080483A (hu) |
| CN (1) | CN1418206A (hu) |
| AT (1) | AT5093U1 (hu) |
| AU (1) | AU2001244086A1 (hu) |
| BG (1) | BG107049A (hu) |
| BR (1) | BR0109180A (hu) |
| CA (1) | CA2402869A1 (hu) |
| CH (1) | CH692148A5 (hu) |
| CZ (1) | CZ20023406A3 (hu) |
| DE (1) | DE10190485T1 (hu) |
| EA (1) | EA200200982A1 (hu) |
| ES (1) | ES2159271B1 (hu) |
| HR (1) | HRP20020757A2 (hu) |
| HU (1) | HUP0300134A2 (hu) |
| IL (1) | IL151487A0 (hu) |
| IS (1) | IS6522A (hu) |
| MX (1) | MXPA02008652A (hu) |
| NO (1) | NO20024197D0 (hu) |
| NZ (1) | NZ521059A (hu) |
| PL (1) | PL360115A1 (hu) |
| SK (1) | SK14812002A3 (hu) |
| TR (1) | TR200202168T2 (hu) |
| WO (1) | WO2001068632A1 (hu) |
| ZA (1) | ZA200206802B (hu) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TR200102957T2 (tr) | 1999-04-14 | 2004-12-21 | H. Lundbeck A/S | Sitalopram hazırlanması için metod. |
| US6310222B1 (en) * | 1999-11-01 | 2001-10-30 | Sumika Fine Chemicals Co., Ltd. | Production method of 5-phthalancarbonitrile compound, intermediate therefor and production method of the intermediate |
| US6433196B1 (en) * | 2000-02-17 | 2002-08-13 | Sumika Fine Chemicals Co., Ltd. | Production method of citalopram, intermediate therefor and production method of the intermediate |
| IES20010157A2 (en) | 2000-03-03 | 2002-03-06 | Lundbeck & Co As H | Method for the preparation of citalopram |
| CN1427835A (zh) * | 2000-03-13 | 2003-07-02 | H·隆德贝克有限公司 | 5－取代的1－(4－氟苯基)－1,3－二氢异苯并呋喃的分步烷基化 |
| NZ521201A (en) | 2000-03-13 | 2004-02-27 | H | Method for the preparation of citalopram |
| IES20010206A2 (en) | 2000-03-13 | 2002-03-06 | Lundbeck & Co As H | Method for the preparation of citalopram |
| ATE257832T1 (de) | 2000-03-14 | 2004-01-15 | Lundbeck & Co As H | Verfahren zur herstellung von 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 |
| TWI306846B (en) | 2002-08-12 | 2009-03-01 | Lundbeck & Co As H | Method for the separation of intermediates which may be used for the preparation of escitalopram |
| US20050154052A1 (en) * | 2003-03-24 | 2005-07-14 | Hetero Drugs Limited | Novel crystalline forms of (s)-citalopram oxalate |
| TWI339651B (en) | 2004-02-12 | 2011-04-01 | Lundbeck & Co As H | Method for the separation of intermediates which may be used for the preparation of escitalopram |
| WO2006021971A2 (en) | 2004-08-23 | 2006-03-02 | Sun Pharmaceutical Industries Limited | 'process for preparation of citalopram and enantiomers' |
| JP2006176490A (ja) * | 2004-11-29 | 2006-07-06 | Sumitomo Chemical Co Ltd | ５−フタランカルボニトリル及びシタロプラムの製造方法 |
| CN102190641A (zh) * | 2011-03-23 | 2011-09-21 | 四川科伦药物研究有限公司 | 一种制备西酞普兰和艾司西酞普兰关键中间体的方法 |
| CN105037304B (zh) * | 2015-06-11 | 2018-12-04 | 福州大学 | 一种合成3-卤亚甲基-2,3-二氢苯并呋喃类化合物的方法 |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1143702A (hu) * | 1965-03-18 | |||
| GB1526331A (en) * | 1976-01-14 | 1978-09-27 | Kefalas As | Phthalanes |
| GB8419963D0 (en) * | 1984-08-06 | 1984-09-12 | Lundbeck & Co As H | Intermediate compound and method |
| GB8814057D0 (en) * | 1988-06-14 | 1988-07-20 | Lundbeck & Co As H | New enantiomers & their isolation |
| US5296507A (en) * | 1990-09-06 | 1994-03-22 | H.Lundbeck A/S | Treatment of cerbrovascular disorders |
| EP0613720A1 (en) * | 1993-03-05 | 1994-09-07 | Duphar International Research B.V | Nickel catalyst for the cyanation of aromatic halides |
| DE19626659A1 (de) * | 1996-07-03 | 1998-01-08 | Basf Ag | Verfahren zur Herstellung von Phthaliden |
| DE19627697A1 (de) * | 1996-07-10 | 1998-01-15 | Basf Ag | Verfahren zur Herstellung von Phthaliden |
| PT1015416E (pt) * | 1997-07-08 | 2002-03-28 | Lundbeck & Co As H | Metodo para a producao de citalopram |
| UA62985C2 (en) * | 1997-11-10 | 2004-01-15 | Lunnbeck As H | A method for the preparation of citalopram |
| AU738359B2 (en) * | 1997-11-11 | 2001-09-13 | H. Lundbeck A/S | Method for the preparation of citalopram |
| HU228576B1 (en) * | 1998-10-20 | 2013-04-29 | Lundbeck & Co As H | Method for the preparation of citalopram |
| CA2356188C (en) * | 1998-12-23 | 2006-05-23 | H. Lundbeck A/S | Method for the preparation of 5-cyanophthalide |
| AR022329A1 (es) * | 1999-01-29 | 2002-09-04 | Lundbeck & Co As H | Metodo para la preparacion de 5-cianoftalida |
| TR200102957T2 (tr) * | 1999-04-14 | 2004-12-21 | H. Lundbeck A/S | Sitalopram hazırlanması için metod. |
| ITMI991581A1 (it) * | 1999-06-25 | 2001-01-15 | Lundbeck & Co As H | Metodo per la preparazione di citalopram |
| ITMI991579A1 (it) * | 1999-06-25 | 2001-01-15 | Lundbeck & Co As H | Metodo per la preparazione di citalopram |
| ES2169709A1 (es) * | 1999-10-25 | 2002-07-01 | Lundbeck & Co As H | Metodo para la preparacion de citalopram |
| US6310222B1 (en) * | 1999-11-01 | 2001-10-30 | Sumika Fine Chemicals Co., Ltd. | Production method of 5-phthalancarbonitrile compound, intermediate therefor and production method of the intermediate |
| AR026063A1 (es) * | 1999-11-01 | 2002-12-26 | Lundbeck & Co As H | Metodo para la preparacion de 5-carboxiftalida. |
| US6433196B1 (en) | 2000-02-17 | 2002-08-13 | Sumika Fine Chemicals Co., Ltd. | Production method of citalopram, intermediate therefor and production method of the intermediate |
| IES20010143A2 (en) * | 2000-02-24 | 2001-07-25 | Lundbeck & Co As H | Method for the preparation of citalopram |
| FR2805812A1 (fr) * | 2000-02-24 | 2001-09-07 | Lundbeck & Co As H | Procede de preparation du citalopram |
| WO2002004435A1 (en) * | 2000-07-06 | 2002-01-17 | H. Lundbeck A/S | Method for the preparation of citalopram |
| IL144817A0 (en) * | 2000-08-18 | 2002-06-30 | Lundbeck & Co As H | Method for the preparation of citalopram |
| EP1181713B1 (en) * | 2000-12-22 | 2004-09-29 | H. Lundbeck A/S | Method for the preparation of pure citalopram |
| PT1181272E (pt) * | 2000-12-28 | 2003-01-31 | Lundbeck & Co As H | Processo para a preparacao de citalopram puro |
-
2001
- 2001-03-16 WO PCT/DK2001/000186 patent/WO2001068632A1/en not_active IP Right Cessation
- 2001-03-16 CZ CZ20023406A patent/CZ20023406A3/cs unknown
- 2001-03-16 HU HU0300134A patent/HUP0300134A2/hu unknown
- 2001-03-16 BR BR0109180-8A patent/BR0109180A/pt not_active IP Right Cessation
- 2001-03-16 PL PL36011501A patent/PL360115A1/xx not_active Application Discontinuation
- 2001-03-16 EA EA200200982A patent/EA200200982A1/ru unknown
- 2001-03-16 JP JP2001567724A patent/JP2003527388A/ja not_active Withdrawn
- 2001-03-16 CA CA002402869A patent/CA2402869A1/en not_active Abandoned
- 2001-03-16 SK SK1481-2002A patent/SK14812002A3/sk unknown
- 2001-03-16 DE DE10190485T patent/DE10190485T1/de not_active Ceased
- 2001-03-16 TR TR2002/02168T patent/TR200202168T2/xx unknown
- 2001-03-16 NZ NZ521059A patent/NZ521059A/en unknown
- 2001-03-16 IL IL15148701A patent/IL151487A0/xx unknown
- 2001-03-16 AU AU2001244086A patent/AU2001244086A1/en not_active Abandoned
- 2001-03-16 EP EP01916932A patent/EP1274699A1/en not_active Withdrawn
- 2001-03-16 ES ES200150038A patent/ES2159271B1/es not_active Expired - Fee Related
- 2001-03-16 CN CN01806598A patent/CN1418206A/zh active Pending
- 2001-03-16 CH CH00866/01A patent/CH692148A5/de not_active IP Right Cessation
- 2001-03-16 KR KR1020027011955A patent/KR20020080483A/ko not_active Application Discontinuation
- 2001-03-16 AT AT0900101U patent/AT5093U1/de not_active IP Right Cessation
- 2001-03-16 MX MXPA02008652A patent/MXPA02008652A/es unknown
-
2002
- 2002-08-23 IS IS6522A patent/IS6522A/is unknown
- 2002-08-26 ZA ZA200206802A patent/ZA200206802B/en unknown
- 2002-08-30 US US10/233,132 patent/US20030060640A1/en not_active Abandoned
- 2002-09-02 BG BG107049A patent/BG107049A/xx unknown
- 2002-09-03 NO NO20024197A patent/NO20024197D0/no not_active Application Discontinuation
- 2002-09-18 HR HRP20020757 patent/HRP20020757A2/hr not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| US20030060640A1 (en) | 2003-03-27 |
| NO20024197L (no) | 2002-09-03 |
| ES2159271B1 (es) | 2002-05-01 |
| AT5093U1 (de) | 2002-03-25 |
| MXPA02008652A (es) | 2003-02-24 |
| CN1418206A (zh) | 2003-05-14 |
| IS6522A (is) | 2002-08-23 |
| NO20024197D0 (no) | 2002-09-03 |
| WO2001068632A1 (en) | 2001-09-20 |
| TR200202168T2 (tr) | 2002-12-23 |
| CZ20023406A3 (cs) | 2003-01-15 |
| DE10190485T1 (de) | 2002-03-21 |
| AU2001244086A1 (en) | 2001-09-24 |
| SK14812002A3 (sk) | 2003-02-04 |
| HRP20020757A2 (en) | 2004-12-31 |
| BG107049A (en) | 2003-05-30 |
| CH692148A5 (de) | 2002-02-28 |
| CA2402869A1 (en) | 2001-09-20 |
| EA200200982A1 (ru) | 2003-02-27 |
| IL151487A0 (en) | 2003-04-10 |
| PL360115A1 (en) | 2004-09-06 |
| KR20020080483A (ko) | 2002-10-23 |
| JP2003527388A (ja) | 2003-09-16 |
| BR0109180A (pt) | 2003-05-27 |
| ES2159271A1 (es) | 2001-09-16 |
| NZ521059A (en) | 2004-04-30 |
| ZA200206802B (en) | 2003-11-26 |
| EP1274699A1 (en) | 2003-01-15 |
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