ES2149734T1 - Metodo para la preparacion de citalopram. - Google Patents
Metodo para la preparacion de citalopram.Info
- Publication number
- ES2149734T1 ES2149734T1 ES97945799T ES97945799T ES2149734T1 ES 2149734 T1 ES2149734 T1 ES 2149734T1 ES 97945799 T ES97945799 T ES 97945799T ES 97945799 T ES97945799 T ES 97945799T ES 2149734 T1 ES2149734 T1 ES 2149734T1
- Authority
- ES
- Spain
- Prior art keywords
- formula
- citalopram
- compound
- followed
- preparation
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
Links
- 229960001653 citalopram Drugs 0.000 title abstract 4
- 238000000034 method Methods 0.000 title abstract 2
- 238000002360 preparation method Methods 0.000 title abstract 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 title 1
- 150000001875 compounds Chemical class 0.000 abstract 4
- 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 3
- 239000007818 Grignard reagent Substances 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 238000006193 diazotization reaction Methods 0.000 abstract 2
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 150000004795 grignard reagents Chemical class 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- 238000006798 ring closing metathesis reaction Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/68—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings and hydroxy groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/22—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/30—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by doubly-bound oxygen atoms
- C07C233/33—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by doubly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/42—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
- C07C233/43—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of a saturated carbon skeleton
-
- 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
-
- 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
- C07D307/88—Benzo [c] furans; Hydrogenated benzo [c] furans with one oxygen atom directly attached in position 1 or 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Un método para la preparación de citalopram, que comprende las etapas de: a) hacer reaccionar un compuesto de Fórmula IV Fórmula IV en la que R1 es H o alquil C1-6-carbonilo, con un reactivo de Grignard de 4-halógeno-fluorofenilo; b) hacer reaccionar el compuesto resultante de Fórmula V Fórmula V en la que R1 se define como antes, con un reactivo de Grignard de 3-halógeno-N,N-dimetilpropilamina: c) efectuar el cierre de anillo del compuesto resultante de Fórmula VI Fórmula VI en la que R1 se define como antes, y d) convertir el compuesto resultante de Formula VII Fórmula VII en la que R1 se define como antes en el correspondiente 5- ciano-derivado, es decir, citalopram a) cuando R1 es alquil C1-6-carbonilo, por hidrólisis de grupo alquil C1-6-carbonilamino, R1-NH-, al correspondiente grupo amino en el que R1 es H, seguida de diazotación y reacción con CN-, y b) cuando R1 es H por diazotación seguida de reacción con CN-, seguido por aislamiento de citalopramcomo base o sal farmaceuticamente aceptable del mismo.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN97182416A CN1286687A (zh) | 1997-11-11 | 1997-11-11 | 制备西酞普兰的方法 |
| PCT/DK1997/000513 WO1998019512A2 (en) | 1997-11-11 | 1997-11-11 | Method for the preparation of citalopram |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ES2149734T1 true ES2149734T1 (es) | 2000-11-16 |
| ES2149734T3 ES2149734T3 (es) | 2003-02-16 |
Family
ID=37709785
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES97945799T Expired - Lifetime ES2149734T3 (es) | 1997-11-11 | 1997-11-11 | Metodo para la preparacion de citalopram. |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US6258842B1 (es) |
| EP (1) | EP1042310B1 (es) |
| JP (1) | JP3813820B2 (es) |
| CN (1) | CN1286687A (es) |
| AT (1) | ATE221522T1 (es) |
| AU (1) | AU738359B2 (es) |
| BR (1) | BR9714925A (es) |
| CA (1) | CA2291072C (es) |
| CZ (1) | CZ292911B6 (es) |
| DE (2) | DE1042310T1 (es) |
| DK (1) | DK1042310T3 (es) |
| EA (1) | EA002770B1 (es) |
| ES (1) | ES2149734T3 (es) |
| HU (1) | HUP0002953A3 (es) |
| IS (1) | IS2009B (es) |
| SK (1) | SK283907B6 (es) |
| TR (1) | TR200001341T2 (es) |
| UA (1) | UA62984C2 (es) |
| WO (1) | WO1998019512A2 (es) |
| ZA (1) | ZA9810058B (es) |
Families Citing this family (57)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA62985C2 (en) | 1997-11-10 | 2004-01-15 | Lunnbeck As H | A method for the preparation of citalopram |
| KR100411505B1 (ko) * | 1998-10-20 | 2003-12-18 | 하. 룬트벡 아크티에 셀스카브 | 시탈로프람의 제조방법 |
| 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 |
| ATE237604T1 (de) | 1999-04-14 | 2003-05-15 | Lundbeck & Co As H | Verfahren zur herstellung von citalopram |
| US6245782B1 (en) | 1999-05-17 | 2001-06-12 | Heartdrug Research L.L.C. | Methods of inhibiting platelet activation with selective serotonin reuptake inhibitors |
| 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 |
| ITMI991486A1 (it) * | 1999-07-06 | 2001-01-06 | Vis Farmaceutici S P A | Processo per la sintesi di citalopram |
| AR021155A1 (es) * | 1999-07-08 | 2002-06-12 | Lundbeck & Co As H | Tratamiento de desordenes neuroticos |
| DE69920526T2 (de) | 1999-10-25 | 2006-02-23 | H. Lundbeck A/S | Verfahren zur herstellung von citalopram |
| ES2229774T3 (es) | 1999-10-25 | 2005-04-16 | H. Lundbeck A/S | Metodo para la preparacion de citalopram. |
| AR026063A1 (es) | 1999-11-01 | 2002-12-26 | Lundbeck & Co As H | Metodo para la preparacion de 5-carboxiftalida. |
| SI1246812T1 (en) | 1999-12-28 | 2004-08-31 | H. Lundbeck A/S | Method for the preparation of citalopram |
| HUP0203840A3 (en) * | 1999-12-30 | 2005-02-28 | Lundbeck & Co As H | Method for the preparation of citalopram |
| IL150561A0 (en) | 2000-01-14 | 2003-02-12 | Lundbeck & Co As H | Method for the preparation of 5-cyanophthalide |
| NL1017415C1 (nl) | 2000-02-24 | 2001-05-18 | Lundbeck & Co As H | Werkwijze voor de bereiding van Citalopram. |
| IES20010157A2 (en) | 2000-03-03 | 2002-03-06 | Lundbeck & Co As H | Method for the preparation of citalopram |
| GB0005477D0 (en) | 2000-03-07 | 2000-04-26 | Resolution Chemicals Limited | Process for the preparation of citalopram |
| IES20010206A2 (en) | 2000-03-13 | 2002-03-06 | Lundbeck & Co As H | Method for the preparation of citalopram |
| CN1429219A (zh) | 2000-03-13 | 2003-07-09 | H·隆德贝克有限公司 | 制备西酞普兰的方法 |
| GB2357762B (en) * | 2000-03-13 | 2002-01-30 | Lundbeck & Co As H | Crystalline base of citalopram |
| CA2402553A1 (en) | 2000-03-13 | 2001-09-20 | H. Lundbeck A/S | Stepwise alkylation of 5-substituted 1-(4-fluorophenyl)-1,3-dihydroisobenzofurans |
| ATE257832T1 (de) | 2000-03-14 | 2004-01-15 | Lundbeck & Co As H | Verfahren zur herstellung von citalopram |
| TR200202168T2 (tr) * | 2000-03-16 | 2002-12-23 | H. Lundbeck A/S | 5-Siyano-1-(4-Florofenil)-1,3-Dihidroizobenzofuranların preparasyon metodu |
| AR032455A1 (es) * | 2000-05-12 | 2003-11-12 | Lundbeck & Co As H | Metodo para la preparacion de citalopram, un intermediario empleado en el metodo, un metodo para la preparacion del intermediario empleado en el metodo y composicion farmaceutica antidepresiva |
| US6879110B2 (en) * | 2000-07-27 | 2005-04-12 | Semiconductor Energy Laboratory Co., Ltd. | Method of driving display device |
| FI20011621A (fi) * | 2000-08-18 | 2002-02-19 | Lundbeck & Co As H | Menetelmä sitalopraamin valmistamiseksi |
| IT1319686B1 (it) * | 2000-12-12 | 2003-10-23 | C D Farmasint S R L | Procedimento di preparazione di citalopram. |
| EA003581B1 (ru) * | 2000-12-22 | 2003-06-26 | Х.Лундбекк А/С | Способ получения чистого циталопрама |
| DE10112828C1 (de) * | 2000-12-28 | 2002-11-21 | Lundbeck & Co As H | Verfahren zur Herstellung von Citalopram |
| EA003459B1 (ru) * | 2000-12-28 | 2003-06-26 | Х.Лундбекк А/С | Способ получения чистого циталопрама |
| CA2435925A1 (en) | 2001-01-30 | 2002-08-08 | Orion Corporation Fermion | Process for the preparation of 1-(3-dimethylaminopropyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile |
| EA200301195A1 (ru) * | 2001-05-01 | 2004-04-29 | Х. Лундбекк А/С | Применение энантиомерно чистого эсциталопрама |
| BG65271B1 (bg) * | 2001-06-18 | 2007-11-30 | H. Lundbeck A/S | Метод за получаване на циталопрам |
| EA006213B1 (ru) | 2001-07-31 | 2005-10-27 | Х. Лундбекк А/С | Кристаллическая композиция, содержащая эсциталопрам |
| IS7239A (is) * | 2001-12-14 | 2004-04-29 | H. Lundbeck A/S | Aðferð til framleiðslu á essítalóprami |
| US7148364B2 (en) | 2002-01-07 | 2006-12-12 | Sun Pharmaceutical Industries | Process for the preparation of 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofuran carbonitrile |
| HU0200980D0 (es) * | 2002-03-14 | 2002-05-29 | Gabor S Pal Dr | |
| BG65515B1 (bg) * | 2002-07-26 | 2008-10-31 | H. Lundbeck A/S | Метод за получаване на 5-цианофталид |
| 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 |
| US6812355B2 (en) | 2002-10-22 | 2004-11-02 | Sekhsaria Chemicals Limited | Process for the manufacture of citalopram hydrobromide from 5-bromophthalide |
| ITMI20030479A1 (it) * | 2003-03-13 | 2004-09-14 | Adorkem Technology S P A | Procedimento per la preparazione di un ciano-isobenzofurano. |
| US6781003B1 (en) * | 2003-06-09 | 2004-08-24 | Aurobindo Pharma Ltd. | Preparation of pure citalopram |
| EP1486492A3 (en) | 2003-06-10 | 2005-02-23 | Sun Pharmaceuticals Industries Ltd. | A process for hydrogenolysis of [1-(3-dimethylamino)propyl)]-1-(4-fluorophenyl)-1,3-dihydro-5-halo-isobenzofuran. |
| EP1506963B1 (en) * | 2003-10-28 | 2005-04-13 | Adorkem Technology SpA | Method for the preparation of citalopram |
| 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 |
| WO2006021971A2 (en) | 2004-08-23 | 2006-03-02 | Sun Pharmaceutical Industries Limited | 'process for preparation of citalopram and enantiomers' |
| WO2006103550A1 (en) * | 2005-03-31 | 2006-10-05 | Ranbaxy Laboratories Limited | Processes for the preparation of citalopram and its intermediate 5-aminophthalide |
| US7834201B2 (en) | 2005-06-22 | 2010-11-16 | H. Lundbeck A/S | Crystalline base of escitalopram and orodispersible tablets comprising escitalopram base |
| TWI358407B (en) | 2005-06-22 | 2012-02-21 | Lundbeck & Co As H | Crystalline base of escitalopram and orodispersibl |
| CN100391952C (zh) * | 2005-07-12 | 2008-06-04 | 广东西陇化工有限公司 | 西酞普兰盐的制备方法 |
| US9339500B2 (en) * | 2008-03-04 | 2016-05-17 | Intra-Cellular Therapies, Inc. | Methods of treating vasomotor symptoms |
| CN105801329B (zh) * | 2016-04-29 | 2017-11-28 | 阜阳欣奕华材料科技有限公司 | 一种晕苯的制备方法 |
| CN105801333B (zh) * | 2016-04-29 | 2017-12-22 | 江苏佳麦化工有限公司 | 一种晕苯的制备方法 |
| CN105801328B (zh) * | 2016-04-29 | 2017-12-08 | 浙江瑞灿科技有限公司 | 一种晕苯的制备方法 |
| CN106748627A (zh) * | 2016-11-14 | 2017-05-31 | 苏州市罗森助剂有限公司 | 一种一锅法制备3,5‑二甲基溴苯的方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1143703A (es) | 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 |
| NZ243065A (en) | 1991-06-13 | 1995-07-26 | Lundbeck & Co As H | Piperidine derivatives and pharmaceutical compositions |
| UA62985C2 (en) | 1997-11-10 | 2004-01-15 | Lunnbeck As H | A method for the preparation of citalopram |
-
1997
- 1997-11-11 EA EA200000511A patent/EA002770B1/ru not_active IP Right Cessation
- 1997-11-11 BR BR9714925-0A patent/BR9714925A/pt not_active Application Discontinuation
- 1997-11-11 UA UA2000052827A patent/UA62984C2/uk unknown
- 1997-11-11 EP EP97945799A patent/EP1042310B1/en not_active Expired - Lifetime
- 1997-11-11 JP JP2000583315A patent/JP3813820B2/ja not_active Expired - Fee Related
- 1997-11-11 ES ES97945799T patent/ES2149734T3/es not_active Expired - Lifetime
- 1997-11-11 DK DK97945799T patent/DK1042310T3/da active
- 1997-11-11 WO PCT/DK1997/000513 patent/WO1998019512A2/en active IP Right Grant
- 1997-11-11 SK SK682-2000A patent/SK283907B6/sk unknown
- 1997-11-11 CN CN97182416A patent/CN1286687A/zh active Pending
- 1997-11-11 CZ CZ20001736A patent/CZ292911B6/cs not_active IP Right Cessation
- 1997-11-11 DE DE1042310T patent/DE1042310T1/de active Pending
- 1997-11-11 HU HU0002953A patent/HUP0002953A3/hu unknown
- 1997-11-11 AU AU51168/98A patent/AU738359B2/en not_active Ceased
- 1997-11-11 TR TR2000/01341T patent/TR200001341T2/xx unknown
- 1997-11-11 AT AT97945799T patent/ATE221522T1/de not_active IP Right Cessation
- 1997-11-11 CA CA002291072A patent/CA2291072C/en not_active Expired - Fee Related
- 1997-11-11 DE DE69714480T patent/DE69714480T2/de not_active Expired - Fee Related
-
1998
- 1998-11-03 ZA ZA9810058A patent/ZA9810058B/xx unknown
-
2000
- 2000-04-18 IS IS5461A patent/IS2009B/is unknown
- 2000-04-28 US US09/564,365 patent/US6258842B1/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ATE221522T1 (de) | 2002-08-15 |
| WO1998019512A2 (en) | 1998-05-14 |
| AU5116898A (en) | 1998-05-29 |
| JP3813820B2 (ja) | 2006-08-23 |
| SK6822000A3 (en) | 2000-10-09 |
| DE69714480D1 (de) | 2002-09-05 |
| IS5461A (is) | 2000-04-18 |
| CZ292911B6 (cs) | 2004-01-14 |
| UA62984C2 (en) | 2004-01-15 |
| BR9714925A (pt) | 2003-07-22 |
| CN1286687A (zh) | 2001-03-07 |
| IS2009B (is) | 2005-05-13 |
| HUP0002953A2 (hu) | 2001-04-28 |
| AU738359B2 (en) | 2001-09-13 |
| JP2002530295A (ja) | 2002-09-17 |
| ES2149734T3 (es) | 2003-02-16 |
| EP1042310A2 (en) | 2000-10-11 |
| ZA9810058B (en) | 1999-05-05 |
| WO1998019512A3 (en) | 1998-08-13 |
| DE69714480T2 (de) | 2003-03-06 |
| TR200001341T2 (tr) | 2000-11-21 |
| DK1042310T3 (da) | 2002-12-02 |
| US6258842B1 (en) | 2001-07-10 |
| DE1042310T1 (de) | 2001-04-19 |
| EA200000511A1 (ru) | 2000-10-30 |
| EP1042310B1 (en) | 2002-07-31 |
| CZ20001736A3 (cs) | 2000-10-11 |
| CA2291072A1 (en) | 1998-05-14 |
| CA2291072C (en) | 2002-08-20 |
| SK283907B6 (sk) | 2004-04-06 |
| EA002770B1 (ru) | 2002-08-29 |
| HUP0002953A3 (en) | 2002-12-28 |
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