KR100612480B1 - Ｓ-ｎ,ｎ'-비스[2-히드록시-1-(히드록시메틸)에틸]-5-[(2-히드록시-1-옥소프로필)-아미노]-2,4,6-트리요오도-1,3-벤젠디카르복사미드의 제조방법 - Google Patents
Ｓ-ｎ,ｎ'-비스[2-히드록시-1-(히드록시메틸)에틸]-5-[(2-히드록시-1-옥소프로필)-아미노]-2,4,6-트리요오도-1,3-벤젠디카르복사미드의 제조방법 Download PDFInfo
- Publication number
- KR100612480B1 KR100612480B1 KR1020007012448A KR20007012448A KR100612480B1 KR 100612480 B1 KR100612480 B1 KR 100612480B1 KR 1020007012448 A KR1020007012448 A KR 1020007012448A KR 20007012448 A KR20007012448 A KR 20007012448A KR 100612480 B1 KR100612480 B1 KR 100612480B1
- Authority
- KR
- South Korea
- Prior art keywords
- solvent
- amino
- hydroxy
- oxopropyl
- triiodo
- 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.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims abstract description 33
- -1 2-hydroxy-1-oxopropyl Chemical group 0.000 title claims abstract description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 title claims description 8
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 title claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 title claims description 7
- NAYYNDKKHOIIOD-UHFFFAOYSA-N phthalamide Chemical compound NC(=O)C1=CC=CC=C1C(N)=O NAYYNDKKHOIIOD-UHFFFAOYSA-N 0.000 title 1
- 239000002904 solvent Substances 0.000 claims abstract description 30
- 150000001875 compounds Chemical class 0.000 claims description 36
- 229920005989 resin Polymers 0.000 claims description 30
- 239000011347 resin Substances 0.000 claims description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
- 125000000129 anionic group Chemical group 0.000 claims description 14
- 125000002091 cationic group Chemical group 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 13
- KJJPLEZQSCZCKE-UHFFFAOYSA-N 2-aminopropane-1,3-diol Chemical compound OCC(N)CO KJJPLEZQSCZCKE-UHFFFAOYSA-N 0.000 claims description 11
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 11
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 10
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 5
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 5
- 229940093475 2-ethoxyethanol Drugs 0.000 claims description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 4
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical group CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 claims 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 238000002360 preparation method Methods 0.000 abstract description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 abstract 1
- 229940035437 1,3-propanediol Drugs 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 abstract 1
- 239000000047 product Substances 0.000 description 19
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 16
- 238000001704 evaporation Methods 0.000 description 13
- 230000008020 evaporation Effects 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 238000004128 high performance liquid chromatography Methods 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 9
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 238000005755 formation reaction Methods 0.000 description 8
- 239000012535 impurity Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000013557 residual solvent Substances 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 7
- XQZXYNRDCRIARQ-LURJTMIESA-N iopamidol Chemical compound C[C@H](O)C(=O)NC1=C(I)C(C(=O)NC(CO)CO)=C(I)C(C(=O)NC(CO)CO)=C1I XQZXYNRDCRIARQ-LURJTMIESA-N 0.000 description 7
- 229960004647 iopamidol Drugs 0.000 description 7
- 238000010907 mechanical stirring Methods 0.000 description 7
- 238000006386 neutralization reaction Methods 0.000 description 7
- 238000007127 saponification reaction Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
- 239000000010 aprotic solvent Substances 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007810 chemical reaction solvent Substances 0.000 description 3
- 239000002872 contrast media Substances 0.000 description 3
- 238000011033 desalting Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000005215 alkyl ethers Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 229920001429 chelating resin Polymers 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical group CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 240000008881 Oenanthe javanica Species 0.000 description 1
- 150000001408 amides Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910052806 inorganic carbonate Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- QZUPTXGVPYNUIT-UHFFFAOYSA-N isophthalamide Chemical compound NC(=O)C1=CC=CC(C(N)=O)=C1 QZUPTXGVPYNUIT-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Chemical group 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/16—Preparation of optical isomers
- C07C231/18—Preparation of optical isomers by stereospecific synthesis
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI98A001005 | 1998-05-08 | ||
| IT98MI001005A IT1299202B1 (it) | 1998-05-08 | 1998-05-08 | Processo per la preparazione della s-n,n'-bis (2-idrossi-1- (idrossimetil)etil) -5-((2-idrossi-1-ossopropil)ammino)-2,4,6-triiodo |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20010071221A KR20010071221A (ko) | 2001-07-28 |
| KR100612480B1 true KR100612480B1 (ko) | 2006-08-16 |
Family
ID=11379983
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020007012448A Expired - Lifetime KR100612480B1 (ko) | 1998-05-08 | 1999-04-26 | Ｓ-ｎ,ｎ'-비스[2-히드록시-1-(히드록시메틸)에틸]-5-[(2-히드록시-1-옥소프로필)-아미노]-2,4,6-트리요오도-1,3-벤젠디카르복사미드의 제조방법 |
Country Status (15)
| Country | Link |
|---|---|
| EP (1) | EP1075462B1 (https=) |
| JP (1) | JP4390389B2 (https=) |
| KR (1) | KR100612480B1 (https=) |
| CN (1) | CN100336800C (https=) |
| AT (1) | ATE243676T1 (https=) |
| AU (1) | AU749785B2 (https=) |
| CA (1) | CA2331660C (https=) |
| CZ (1) | CZ293801B6 (https=) |
| DE (1) | DE69909078T2 (https=) |
| DK (1) | DK1075462T3 (https=) |
| ES (1) | ES2201719T3 (https=) |
| IT (1) | IT1299202B1 (https=) |
| NO (1) | NO326203B1 (https=) |
| PT (1) | PT1075462E (https=) |
| WO (1) | WO1999058494A2 (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101098553B1 (ko) * | 2008-04-30 | 2011-12-26 | 주식회사 엘지생명과학 | 이오프로마이드의 신규한 제조방법 |
| EP2365963B1 (en) * | 2008-11-18 | 2017-06-28 | Bracco Imaging S.p.A | Process for the preparation of iodinated contrast agent |
| EP2230227A1 (en) | 2009-03-20 | 2010-09-22 | Bracco Imaging S.p.A | Process for the preparation of triiodinated carboxylic aromatic derivatives |
| HUE040143T2 (hu) | 2012-12-11 | 2019-02-28 | Bracco Imaging Spa | Folyamatos eljárás (S)-2-acetiloxipropionsav elõállítására |
| PT3369724T (pt) | 2013-11-05 | 2021-02-10 | Bracco Imaging Spa | Processo para a preparação de iopamidol |
| EP3154928B1 (en) | 2014-06-10 | 2020-03-04 | Bracco Imaging S.p.A | Method for the preparation of (s)-2-acetyloxypropionic acid and derivatives thereof |
| CN105272899B (zh) * | 2015-11-17 | 2017-09-22 | 浙江海洲制药有限公司 | 一种化合物及其用于合成碘帕醇杂质d、杂质f、杂质g和杂质j的方法 |
| WO2018104228A1 (en) | 2016-12-05 | 2018-06-14 | Bracco Imaging Spa | Mechanochemical synthesis of radiographic agents intermediates |
| CN110687226B (zh) * | 2019-10-18 | 2022-10-25 | 上海明捷医药科技有限公司 | 一种测定碘帕醇中2-氯丙酸含量的方法 |
| EP4452931A1 (en) * | 2021-12-20 | 2024-10-30 | Bracco Imaging SPA | Process for the preparation of 2,4,6-triiodoisophthalic bisamides |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH608189A5 (https=) * | 1974-12-13 | 1978-12-29 | Savac Ag | |
| DE2628517C2 (de) * | 1976-06-23 | 1985-02-21 | Schering AG, 1000 Berlin und 4709 Bergkamen | Dicarbonsäure-bis(3,5-dicarbamoyl-2,4,6-trijodanilid)-Verbindungen, Verfahren zu ihrer Herstellung und Röntgenkontrastmittel |
| DE2928417A1 (de) * | 1979-07-12 | 1981-01-29 | Schering Ag | Trijodierte basen |
| IT1256163B (it) * | 1992-10-27 | 1995-11-29 | Zambon Spa | Processo per la preparazione di un intermedio della sintesi organica |
| IT1283319B1 (it) * | 1996-03-29 | 1998-04-16 | Zambon Spa | Processo per la preparazione di un intermedio utile nella sintesi di mezzi di contrasto iodurati |
| IT1288114B1 (it) * | 1996-06-13 | 1998-09-10 | Fructamine Spa | Processo per la purificazione di un intermedio |
-
1998
- 1998-05-08 IT IT98MI001005A patent/IT1299202B1/it active IP Right Grant
-
1999
- 1999-04-26 EP EP19990924824 patent/EP1075462B1/en not_active Expired - Lifetime
- 1999-04-26 DK DK99924824T patent/DK1075462T3/da active
- 1999-04-26 JP JP2000548298A patent/JP4390389B2/ja not_active Expired - Lifetime
- 1999-04-26 PT PT99924824T patent/PT1075462E/pt unknown
- 1999-04-26 AU AU41356/99A patent/AU749785B2/en not_active Expired
- 1999-04-26 CZ CZ20004124A patent/CZ293801B6/cs not_active IP Right Cessation
- 1999-04-26 WO PCT/EP1999/002804 patent/WO1999058494A2/en not_active Ceased
- 1999-04-26 CN CNB998059226A patent/CN100336800C/zh not_active Expired - Lifetime
- 1999-04-26 ES ES99924824T patent/ES2201719T3/es not_active Expired - Lifetime
- 1999-04-26 AT AT99924824T patent/ATE243676T1/de active
- 1999-04-26 DE DE69909078T patent/DE69909078T2/de not_active Expired - Lifetime
- 1999-04-26 KR KR1020007012448A patent/KR100612480B1/ko not_active Expired - Lifetime
- 1999-04-26 CA CA002331660A patent/CA2331660C/en not_active Expired - Lifetime
-
2000
- 2000-11-07 NO NO20005616A patent/NO326203B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE69909078T2 (de) | 2003-12-18 |
| ITMI981005A1 (it) | 1999-11-08 |
| PT1075462E (pt) | 2003-10-31 |
| DE69909078D1 (de) | 2003-07-31 |
| NO326203B1 (no) | 2008-10-20 |
| CZ20004124A3 (cs) | 2002-03-13 |
| JP4390389B2 (ja) | 2009-12-24 |
| EP1075462A2 (en) | 2001-02-14 |
| CA2331660C (en) | 2008-07-08 |
| NO20005616L (no) | 2000-11-07 |
| AU4135699A (en) | 1999-11-29 |
| CZ293801B6 (cs) | 2004-08-18 |
| WO1999058494A2 (en) | 1999-11-18 |
| IT1299202B1 (it) | 2000-02-29 |
| DK1075462T3 (da) | 2003-10-13 |
| KR20010071221A (ko) | 2001-07-28 |
| CN1302288A (zh) | 2001-07-04 |
| ES2201719T3 (es) | 2004-03-16 |
| EP1075462B1 (en) | 2003-06-25 |
| CN100336800C (zh) | 2007-09-12 |
| NO20005616D0 (no) | 2000-11-07 |
| AU749785B2 (en) | 2002-07-04 |
| CA2331660A1 (en) | 1999-11-18 |
| ATE243676T1 (de) | 2003-07-15 |
| WO1999058494A3 (en) | 2000-01-20 |
| JP2002517381A (ja) | 2002-06-18 |
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