DE19958460A1 - Verfahren zur Herstellung von Epinastine-Hydrochlorid in der hochschmelzenden Kristallmodifikation - Google Patents
Verfahren zur Herstellung von Epinastine-Hydrochlorid in der hochschmelzenden KristallmodifikationInfo
- Publication number
- DE19958460A1 DE19958460A1 DE19958460A DE19958460A DE19958460A1 DE 19958460 A1 DE19958460 A1 DE 19958460A1 DE 19958460 A DE19958460 A DE 19958460A DE 19958460 A DE19958460 A DE 19958460A DE 19958460 A1 DE19958460 A1 DE 19958460A1
- Authority
- DE
- Germany
- Prior art keywords
- epinastine
- hydrochloric acid
- formula
- epinastine hydrochloride
- hydrochloride
- 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.)
- Withdrawn
Links
- WHWZLSFABNNENI-UHFFFAOYSA-N epinastine Chemical compound C1C2=CC=CC=C2C2CN=C(N)N2C2=CC=CC=C21 WHWZLSFABNNENI-UHFFFAOYSA-N 0.000 title claims abstract description 35
- 238000000034 method Methods 0.000 title claims abstract description 34
- 229960002548 epinastine hydrochloride Drugs 0.000 title claims abstract description 24
- 239000013078 crystal Substances 0.000 title claims abstract description 16
- 230000004048 modification Effects 0.000 title claims abstract description 15
- 238000012986 modification Methods 0.000 title claims abstract description 15
- 238000002844 melting Methods 0.000 title claims abstract description 12
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 229960003449 epinastine Drugs 0.000 claims description 11
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 6
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 6
- 230000008018 melting Effects 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 239000008346 aqueous phase Substances 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 3
- 238000010533 azeotropic distillation Methods 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 238000000605 extraction Methods 0.000 claims description 2
- 150000008282 halocarbons Chemical class 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- 239000000047 product Substances 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000000113 differential scanning calorimetry Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- AJUMGSLQADLWKL-UHFFFAOYSA-N 1h-azepine;hydrochloride Chemical compound Cl.N1C=CC=CC=C1 AJUMGSLQADLWKL-UHFFFAOYSA-N 0.000 description 1
- DISXFZWKRTZTRI-UHFFFAOYSA-N 4,5-dihydro-1h-imidazol-2-amine Chemical class NC1=NCCN1 DISXFZWKRTZTRI-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 230000003326 anti-histaminergic effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000003908 quality control method Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Priority Applications (24)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19958460A DE19958460A1 (de) | 1999-12-03 | 1999-12-03 | Verfahren zur Herstellung von Epinastine-Hydrochlorid in der hochschmelzenden Kristallmodifikation |
| US09/716,355 US6403790B1 (en) | 1999-12-03 | 2000-11-20 | Process for the production of epinastine hydrochloride in the high-melting crystal modification |
| MXPA02005330A MXPA02005330A (es) | 1999-12-03 | 2000-11-29 | Procedimiento para la preparacion de hidrocloruro de epinastina en la modificacion cristalina de alto punto de fusion. |
| ES00985110T ES2198368T3 (es) | 1999-12-03 | 2000-11-29 | Metodo para producir hidrocloruro de epinastina en la modificacion cristalina de elevado punto de fusion. |
| CN00816517A CN1402728A (zh) | 1999-12-03 | 2000-11-29 | 制造高熔化结晶变体的依匹那丁氢氯酸的方法 |
| KR1020027007120A KR100737191B1 (ko) | 1999-12-03 | 2000-11-29 | 고융점 결정 변형체인 에피나스틴 하이드로클로라이드의제조방법 |
| PL00355628A PL355628A1 (en) | 1999-12-03 | 2000-11-29 | Method for producing epinastine hydrochloride in the high-melting crystal modification |
| CA002389170A CA2389170C (en) | 1999-12-03 | 2000-11-29 | A process for the production of epinastine hydrochloride in the high-melting crystal modification |
| CZ20021843A CZ20021843A3 (cs) | 1999-12-03 | 2000-11-29 | Způsob výroby hydrochloridu epinastinu |
| EP00985110A EP1237892B1 (de) | 1999-12-03 | 2000-11-29 | Verfahren zur herstellung von epinastine-hydrochlorid in der hochschmelzenden kristallmodifikation |
| PT00985110T PT1237892E (pt) | 1999-12-03 | 2000-11-29 | Processo para a preparacao de cloridrato de epinastina na modificacao cristalina de elevado ponto de fusao |
| IL14971100A IL149711A0 (en) | 1999-12-03 | 2000-11-29 | Method for producing epinastine hydrochloride in the high-melting crystal modification |
| UY26461A UY26461A1 (es) | 1999-12-03 | 2000-11-29 | Procedimiento para la preparación de hidrocloruro de epinastina en la modificación cristalina de alto punto de fusión. |
| EA200200630A EA200200630A1 (ru) | 1999-12-03 | 2000-11-29 | Способ получения гидрохлорида эпинастина в виде кристаллической модификации с высокой температурой плавления |
| DK00985110T DK1237892T3 (da) | 1999-12-03 | 2000-11-29 | Fremgangsmåde til fremstilling af epinastinhydrochlorid i den højtsmeltende krystalmodifikation |
| DE50001920T DE50001920D1 (de) | 1999-12-03 | 2000-11-29 | Verfahren zur herstellung von epinastine-hydrochlorid in der hochschmelzenden kristallmodifikation |
| AT00985110T ATE238306T1 (de) | 1999-12-03 | 2000-11-29 | Verfahren zur herstellung von epinastine- hydrochlorid in der hochschmelzenden kristallmodifikation |
| AU21635/01A AU2163501A (en) | 1999-12-03 | 2000-11-29 | Method for producing epinastine hydrochloride in the high-melting crystal modification |
| PCT/EP2000/011942 WO2001040229A2 (de) | 1999-12-03 | 2000-11-29 | Verfahren zur herstellung von epinastine-hydrochlorid in der hochschmelzenden kristallmodifikation |
| JP2001540984A JP4789383B2 (ja) | 1999-12-03 | 2000-11-29 | 高温融解結晶変態のエピナスチン塩酸塩の生成方法 |
| HU0203501A HUP0203501A2 (hu) | 1999-12-03 | 2000-11-29 | Eljárás epinastin-hidroklorid előállítására magas olvadáspontú kristálymódosulatban |
| BR0016052-0A BR0016052A (pt) | 1999-12-03 | 2000-11-29 | Processo para a preparação de cloridrato de epinastina na modificação de cristal de elevado ponto de fusão |
| ARP000106338A AR026678A1 (es) | 1999-12-03 | 2000-12-01 | Procedimiento para la preparacion de hidrocloruro de epinastina en la modificacion cristalina de alto punto de fusion. |
| CO00092015A CO5251470A1 (es) | 1999-12-03 | 2000-12-01 | Procedimiento para la preparacion de hidrocloruro de epinastina en la modificacion cristalina de alto punto de fusion |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19958460A DE19958460A1 (de) | 1999-12-03 | 1999-12-03 | Verfahren zur Herstellung von Epinastine-Hydrochlorid in der hochschmelzenden Kristallmodifikation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19958460A1 true DE19958460A1 (de) | 2001-06-07 |
Family
ID=7931396
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19958460A Withdrawn DE19958460A1 (de) | 1999-12-03 | 1999-12-03 | Verfahren zur Herstellung von Epinastine-Hydrochlorid in der hochschmelzenden Kristallmodifikation |
| DE50001920T Expired - Lifetime DE50001920D1 (de) | 1999-12-03 | 2000-11-29 | Verfahren zur herstellung von epinastine-hydrochlorid in der hochschmelzenden kristallmodifikation |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE50001920T Expired - Lifetime DE50001920D1 (de) | 1999-12-03 | 2000-11-29 | Verfahren zur herstellung von epinastine-hydrochlorid in der hochschmelzenden kristallmodifikation |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US6403790B1 (https=) |
| EP (1) | EP1237892B1 (https=) |
| JP (1) | JP4789383B2 (https=) |
| KR (1) | KR100737191B1 (https=) |
| CN (1) | CN1402728A (https=) |
| AR (1) | AR026678A1 (https=) |
| AT (1) | ATE238306T1 (https=) |
| AU (1) | AU2163501A (https=) |
| BR (1) | BR0016052A (https=) |
| CA (1) | CA2389170C (https=) |
| CO (1) | CO5251470A1 (https=) |
| CZ (1) | CZ20021843A3 (https=) |
| DE (2) | DE19958460A1 (https=) |
| DK (1) | DK1237892T3 (https=) |
| EA (1) | EA200200630A1 (https=) |
| ES (1) | ES2198368T3 (https=) |
| HU (1) | HUP0203501A2 (https=) |
| IL (1) | IL149711A0 (https=) |
| MX (1) | MXPA02005330A (https=) |
| PL (1) | PL355628A1 (https=) |
| PT (1) | PT1237892E (https=) |
| UY (1) | UY26461A1 (https=) |
| WO (1) | WO2001040229A2 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115448927A (zh) * | 2022-10-20 | 2022-12-09 | 重庆瑞泊莱医药科技有限公司 | 一种氢溴酸依匹斯汀晶型ii及其制备方法 |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19954516A1 (de) * | 1999-11-12 | 2001-05-17 | Boehringer Ingelheim Int | Epinastin-haltige Lösungen |
| JP4298212B2 (ja) * | 2002-03-29 | 2009-07-15 | 大日本印刷株式会社 | 塩酸エピナスチン高融点型結晶の製造法 |
| AU2003250073A1 (en) * | 2002-08-02 | 2004-02-25 | Boehringer Ingelheim International Gmbh | Pharmaceutical formulations comprising combinations of epinastine, pseudoephedrine and methylephedrine |
| KR101386530B1 (ko) | 2006-12-29 | 2014-04-18 | 케이피엑스 라이프사이언스 주식회사 | 순도 및 수율이 향상된3-아미노-9,13ｂ디하이드로-1Ｈ-디벤즈-[ｃ,ｆ]이미다조[1,5-ａ]-아제핀 염산염의 제조방법 |
| CN104098575B (zh) * | 2013-04-15 | 2016-06-01 | 四川科瑞德凯华制药有限公司 | 一种盐酸依匹斯汀晶型及其制备方法和用途 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3008944A1 (de) * | 1980-03-08 | 1981-09-24 | C.H. Boehringer Sohn, 6507 Ingelheim | Dibenzimidazoazepine, ihre herstellung und verwendung |
| DE4102148A1 (de) * | 1991-01-25 | 1992-07-30 | Boehringer Ingelheim Kg | Verfahren zur herstellung von 3-amino-9,13b-dihydro-1h-dibenz-(c,f)imidazol(1,5-a)azepin-hydrochlorid |
| JP3726291B2 (ja) * | 1993-07-05 | 2005-12-14 | 三菱ウェルファーマ株式会社 | 安定な結晶構造を有するベンゾオキサジン化合物およびその製造法 |
| JPH083160A (ja) * | 1994-06-22 | 1996-01-09 | Nippon Kayaku Co Ltd | ６−（１−ｈ−イミダゾール−１−イル）−７−ニトロ−２，３−（１ｈ，４ｈ）−キノキサリンジオン塩酸塩又は硫酸塩の分離精製法 |
| JP3755908B2 (ja) * | 1994-08-17 | 2006-03-15 | 塩野義製薬株式会社 | セファロスポリン化合物の晶析法 |
| JPH0948765A (ja) * | 1995-08-04 | 1997-02-18 | Toyama Chem Co Ltd | 安定な結晶構造を有するトリアゾール誘導体およびその製造法 |
| DE19542281C2 (de) * | 1995-11-14 | 1997-12-04 | Boehringer Ingelheim Kg | Verwendung von Epinastin für die Behandlung der Migräne |
-
1999
- 1999-12-03 DE DE19958460A patent/DE19958460A1/de not_active Withdrawn
-
2000
- 2000-11-20 US US09/716,355 patent/US6403790B1/en not_active Expired - Lifetime
- 2000-11-29 CZ CZ20021843A patent/CZ20021843A3/cs unknown
- 2000-11-29 BR BR0016052-0A patent/BR0016052A/pt not_active Application Discontinuation
- 2000-11-29 AT AT00985110T patent/ATE238306T1/de active
- 2000-11-29 CN CN00816517A patent/CN1402728A/zh active Pending
- 2000-11-29 WO PCT/EP2000/011942 patent/WO2001040229A2/de not_active Ceased
- 2000-11-29 DE DE50001920T patent/DE50001920D1/de not_active Expired - Lifetime
- 2000-11-29 CA CA002389170A patent/CA2389170C/en not_active Expired - Lifetime
- 2000-11-29 HU HU0203501A patent/HUP0203501A2/hu unknown
- 2000-11-29 PT PT00985110T patent/PT1237892E/pt unknown
- 2000-11-29 DK DK00985110T patent/DK1237892T3/da active
- 2000-11-29 PL PL00355628A patent/PL355628A1/xx not_active Application Discontinuation
- 2000-11-29 UY UY26461A patent/UY26461A1/es not_active Application Discontinuation
- 2000-11-29 EA EA200200630A patent/EA200200630A1/ru unknown
- 2000-11-29 AU AU21635/01A patent/AU2163501A/en not_active Abandoned
- 2000-11-29 IL IL14971100A patent/IL149711A0/xx unknown
- 2000-11-29 KR KR1020027007120A patent/KR100737191B1/ko not_active Expired - Lifetime
- 2000-11-29 MX MXPA02005330A patent/MXPA02005330A/es active IP Right Grant
- 2000-11-29 JP JP2001540984A patent/JP4789383B2/ja not_active Expired - Lifetime
- 2000-11-29 ES ES00985110T patent/ES2198368T3/es not_active Expired - Lifetime
- 2000-11-29 EP EP00985110A patent/EP1237892B1/de not_active Expired - Lifetime
- 2000-12-01 AR ARP000106338A patent/AR026678A1/es active IP Right Grant
- 2000-12-01 CO CO00092015A patent/CO5251470A1/es not_active Application Discontinuation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115448927A (zh) * | 2022-10-20 | 2022-12-09 | 重庆瑞泊莱医药科技有限公司 | 一种氢溴酸依匹斯汀晶型ii及其制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2001040229A2 (de) | 2001-06-07 |
| CZ20021843A3 (cs) | 2002-08-14 |
| WO2001040229A3 (de) | 2001-12-06 |
| PT1237892E (pt) | 2003-08-29 |
| DE50001920D1 (de) | 2003-05-28 |
| JP4789383B2 (ja) | 2011-10-12 |
| AR026678A1 (es) | 2003-02-19 |
| MXPA02005330A (es) | 2003-01-28 |
| AU2163501A (en) | 2001-06-12 |
| PL355628A1 (en) | 2004-05-04 |
| US6403790B1 (en) | 2002-06-11 |
| CO5251470A1 (es) | 2003-02-28 |
| UY26461A1 (es) | 2001-07-31 |
| ES2198368T3 (es) | 2004-02-01 |
| BR0016052A (pt) | 2002-07-23 |
| IL149711A0 (en) | 2002-11-10 |
| KR100737191B1 (ko) | 2007-07-10 |
| CN1402728A (zh) | 2003-03-12 |
| CA2389170C (en) | 2008-01-08 |
| ATE238306T1 (de) | 2003-05-15 |
| KR20020058080A (ko) | 2002-07-12 |
| EP1237892A2 (de) | 2002-09-11 |
| HUP0203501A2 (hu) | 2003-03-28 |
| JP2003515536A (ja) | 2003-05-07 |
| DK1237892T3 (da) | 2003-08-04 |
| CA2389170A1 (en) | 2001-06-07 |
| EP1237892B1 (de) | 2003-04-23 |
| EA200200630A1 (ru) | 2002-12-26 |
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