JP2001526678A - 5−アミノ−2,4,6−トリヨード−n,n´−ビス(2,3−ジヒドロキシプロピル)−イソフタルアミドの黄色多形 - Google Patents
5−アミノ−2,4,6−トリヨード−n,n´−ビス(2,3−ジヒドロキシプロピル)−イソフタルアミドの黄色多形Info
- Publication number
- JP2001526678A JP2001526678A JP55014098A JP55014098A JP2001526678A JP 2001526678 A JP2001526678 A JP 2001526678A JP 55014098 A JP55014098 A JP 55014098A JP 55014098 A JP55014098 A JP 55014098A JP 2001526678 A JP2001526678 A JP 2001526678A
- Authority
- JP
- Japan
- Prior art keywords
- bis
- amino
- triiodo
- isophthalamide
- dihydroxypropyl
- 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
- KAEGSAWWVYMWIQ-UHFFFAOYSA-N 5-amino-1-n,3-n-bis(2,3-dihydroxypropyl)-2,4,6-triiodobenzene-1,3-dicarboxamide Chemical compound NC1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I KAEGSAWWVYMWIQ-UHFFFAOYSA-N 0.000 title claims abstract description 12
- 238000002329 infrared spectrum Methods 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 238000002844 melting Methods 0.000 claims description 8
- 230000008018 melting Effects 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- -1 2,3-dihydroxypropyl Chemical group 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 6
- 229960001025 iohexol Drugs 0.000 claims description 5
- NTHXOOBQLCIOLC-UHFFFAOYSA-N iohexol Chemical compound OCC(O)CN(C(=O)C)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I NTHXOOBQLCIOLC-UHFFFAOYSA-N 0.000 claims description 5
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 5
- 239000002872 contrast media Substances 0.000 claims description 4
- AMDBBAQNWSUWGN-UHFFFAOYSA-N Ioversol Chemical compound OCCN(C(=O)CO)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I AMDBBAQNWSUWGN-UHFFFAOYSA-N 0.000 claims description 3
- 229960000780 iomeprol Drugs 0.000 claims description 3
- NJKDOADNQSYQEV-UHFFFAOYSA-N iomeprol Chemical compound OCC(=O)N(C)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I NJKDOADNQSYQEV-UHFFFAOYSA-N 0.000 claims description 3
- 229960000824 iopentol Drugs 0.000 claims description 3
- IUNJANQVIJDFTQ-UHFFFAOYSA-N iopentol Chemical compound COCC(O)CN(C(C)=O)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I IUNJANQVIJDFTQ-UHFFFAOYSA-N 0.000 claims description 3
- 229960004537 ioversol Drugs 0.000 claims description 3
- 238000001556 precipitation Methods 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000002245 particle Substances 0.000 claims description 2
- 238000009792 diffusion process Methods 0.000 claims 1
- 229960004359 iodixanol Drugs 0.000 claims 1
- NBQNWMBBSKPBAY-UHFFFAOYSA-N iodixanol Chemical compound IC=1C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C(I)C=1N(C(=O)C)CC(O)CN(C(C)=O)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I NBQNWMBBSKPBAY-UHFFFAOYSA-N 0.000 claims 1
- 229940126062 Compound A Drugs 0.000 description 26
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 26
- 238000000034 method Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000012045 crude solution Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- GPLRSWGCEGOYCD-UHFFFAOYSA-N 1-N,3-N-bis(2,3-dihydroxypropyl)-2-iodobenzene-1,3-dicarboxamide Chemical compound C1=CC(=C(C(=C1)C(=O)NCC(CO)O)I)C(=O)NCC(CO)O GPLRSWGCEGOYCD-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 description 1
- 238000007126 N-alkylation reaction Methods 0.000 description 1
- 235000010724 Wisteria floribunda Nutrition 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 239000013043 chemical agent Substances 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- RDYMFSUJUZBWLH-UHFFFAOYSA-N endosulfan Chemical compound C12COS(=O)OCC2C2(Cl)C(Cl)=C(Cl)C1(Cl)C2(Cl)Cl RDYMFSUJUZBWLH-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 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
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NAYYNDKKHOIIOD-UHFFFAOYSA-N phthalamide Chemical compound NC(=O)C1=CC=CC=C1C(N)=O NAYYNDKKHOIIOD-UHFFFAOYSA-N 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000011112 process operation Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000010583 slow cooling Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/04—X-ray contrast preparations
- A61K49/0433—X-ray contrast preparations containing an organic halogenated X-ray contrast-enhancing agent
- A61K49/0447—Physical forms of mixtures of two different X-ray contrast-enhancing agents, containing at least one X-ray contrast-enhancing agent which is a halogenated organic compound
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/04—X-ray contrast preparations
- A61K49/0433—X-ray contrast preparations containing an organic halogenated X-ray contrast-enhancing agent
- A61K49/0438—Organic X-ray contrast-enhancing agent comprising an iodinated group or an iodine atom, e.g. iopamidol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/46—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having carbon atoms of carboxamide groups, amino groups and at least three atoms of bromine or iodine, bound to carbon atoms of the same non-condensed six-membered aromatic ring
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Steroid Compounds (AREA)
- Indole Compounds (AREA)
- Polyamides (AREA)
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.黄色多形形態の5−アミノ−2,4,6−トリヨード−N,N'−ビス(2,3−ジヒド ロキシプロピル)−イソフタルアミド。 2.示差走査熱量計において約247〜252℃でピーク融解温度を有する形態の5− アミノ−2,4,6−トリヨード−N,N'−ビス(2,3−ジヒドロキシプロピル)−イソ フタルアミド。 3.以下の主要ピーク:3330,3244,2929,1641,1564,1402,1277,1228,11 15,1032,957,690,631および440cm-1を示す拡散反射赤外スペクトルを有する 点に特徴のある形態の5−アミノ−2,4,6−トリヨード−N,N'−ビス(2,3−ジヒ ドロキシプロピル)−イソフタルアミド。 4.以下のX線粉末回折パターン: (ここでw=弱い、m=中程度、s=強い、v=非常に、d=拡散)を有す ることを特徴とする形態の5−アミノ−2,4,6−トリヨード−N,N'−ビス(2,3− ジヒドロキシプロピル)−イソフタルアミド。 5.150〜500μmの平均粒径を有する請求項1〜4のいずれか1項に記載の5− アミノ−2,4,6−トリヨード−N,N'−ビス(2,3−ジヒドロキシプロピル)−イソ フタルアミド。 6.5−アミノ−2,4,6−トリヨード−N,N'−ビス(2,3−ジヒドロキシプロピル )−イソフタルアミドの溶液を冷却することからなるが、その冷却を5−アミノ −2,4,6−トリヨード−N,N'−ビス(2,3−ジヒドロキシプロピル)−イソフタル アミドの沈殿期間中、7℃/時より低い温度で実施することを特徴とする、黄色 多形形態の5−アミノ−2,4,6−トリヨード−N,N'−ビス(2,3−ジヒドロキシプ ロピル)−イソフタルアミドの製造方法。 7.ヨウ素化X線造影剤の調製における黄色多形形態の5−アミノ−2,4,6−ト リヨード−N,N'−ビス(2,3−ジヒドロキシプロピル)−イソフタルアミドの使 用。 8.イオヘキソール、イオペントール、イオジキサノール、イオベルソールおよ びイオメプロールから選択される前記剤の調製における請求項7記載の使用。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9710726.2 | 1997-05-23 | ||
GBGB9710726.2A GB9710726D0 (en) | 1997-05-23 | 1997-05-23 | Compound |
PCT/GB1998/001492 WO1998052911A1 (en) | 1997-05-23 | 1998-05-22 | Yellow polymorph of 5-amino-2,4,6-triiodo-n,n'-bis(2,3-dihydroxypropyl)-isophthalamide |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2001526678A true JP2001526678A (ja) | 2001-12-18 |
JP4476366B2 JP4476366B2 (ja) | 2010-06-09 |
Family
ID=10812988
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP55014098A Expired - Lifetime JP4476366B2 (ja) | 1997-05-23 | 1998-05-22 | 5−アミノ−2,4,6−トリヨード−n,n´−ビス(2,3−ジヒドロキシプロピル)−イソフタルアミドの黄色多形 |
Country Status (18)
Country | Link |
---|---|
US (1) | US6337422B1 (ja) |
EP (1) | EP0983230B1 (ja) |
JP (1) | JP4476366B2 (ja) |
KR (1) | KR100543856B1 (ja) |
CN (1) | CN1161324C (ja) |
AT (1) | ATE256101T1 (ja) |
AU (1) | AU725565B2 (ja) |
BR (1) | BRPI9809153B8 (ja) |
CA (1) | CA2290544A1 (ja) |
CZ (1) | CZ297243B6 (ja) |
DE (1) | DE69820435T2 (ja) |
GB (1) | GB9710726D0 (ja) |
HU (1) | HU224128B1 (ja) |
IL (1) | IL133100A (ja) |
NO (1) | NO327490B1 (ja) |
PL (1) | PL190905B1 (ja) |
PT (1) | PT983230E (ja) |
WO (1) | WO1998052911A1 (ja) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7524515B2 (en) * | 2003-01-10 | 2009-04-28 | Mutual Pharmaceuticals, Inc. | Pharmaceutical safety dosage forms |
DE602007012208D1 (de) | 2006-02-15 | 2011-03-10 | Ge Healthcare As | Kontrastmittel |
US7662859B2 (en) | 2007-02-16 | 2010-02-16 | Ge Healthcare As | Contrast agents |
JP2012514622A (ja) | 2009-01-09 | 2012-06-28 | ジーイー・ヘルスケア・アクスイェ・セルスカプ | 造影製剤組成物 |
US20110021834A1 (en) * | 2009-07-21 | 2011-01-27 | Ge Healthcare As | Continuous process of preparing intermediate for non-ionic x-ray contrast agents |
US20110021833A1 (en) * | 2009-07-21 | 2011-01-27 | Ge Healthcare As | Crystallization of an intermediate for synthesizing non-ionic x-ray contrast agents |
EP2281807A1 (en) * | 2009-07-21 | 2011-02-09 | GE Healthcare AS | Decolorizing 5-amino-N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide, a contrast media intermediate |
JP6210988B2 (ja) | 2011-09-19 | 2017-10-11 | オレクソ・アクチエボラゲット | オピオイド依存を治療するための新規乱用耐性医薬組成物 |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5321137A (en) * | 1976-06-11 | 1978-02-27 | Serukapeto | Xxray contrast medium |
JPS55129298A (en) * | 1979-03-23 | 1980-10-06 | Mallinckrodt Chemical Works | N*n**bis*2*33dihydroxypropyl**2*4*66triiodoo 55*22ketoollgulonamido*isophthalamide and irridiative composition containing it |
JPS58131970A (ja) * | 1982-01-11 | 1983-08-06 | マリンクロツド・インコ−ポレイテツド | X線造影剤 |
JPH03504124A (ja) * | 1988-03-01 | 1991-09-12 | マリンクロット,インコーポレイテッド | 非イオン性x線コントラスト剤、組成物及び方法 |
JPH06506954A (ja) * | 1991-04-16 | 1994-08-04 | マリンクロッド・メディカル・インコーポレイテッド | 5−アミノ−n,n’−ビス(2,3−ジヒドロキシプロピル)−2,4,6−トリヨードイソフタルアミドの乾燥における共沸蒸留の使用 |
JPH10505856A (ja) * | 1994-09-23 | 1998-06-09 | ニコムド イメージング エイエス | ヨウ素化x線コントラスト媒体 |
JPH11505827A (ja) * | 1995-05-24 | 1999-05-25 | ナイコムド イメージング エーエス | ヨウ素化方法 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5013865A (en) * | 1988-04-06 | 1991-05-07 | Mallinckrodt, Inc. | Process for the preparation of 2,4,6-triiodo-5-amino-N-alkylisophthalamic acid and 2,4,6-triiodo-5-amino-isophthalamide compounds |
WO1995035122A1 (en) * | 1994-06-21 | 1995-12-28 | Mallinckrodt Medical, Inc. | Improved synthesis of ioversol using phosphoric acid modified co-addition |
-
1997
- 1997-05-23 GB GBGB9710726.2A patent/GB9710726D0/en active Pending
-
1998
- 1998-05-22 CN CNB988053217A patent/CN1161324C/zh not_active Expired - Lifetime
- 1998-05-22 JP JP55014098A patent/JP4476366B2/ja not_active Expired - Lifetime
- 1998-05-22 WO PCT/GB1998/001492 patent/WO1998052911A1/en active IP Right Grant
- 1998-05-22 EP EP98922947A patent/EP0983230B1/en not_active Expired - Lifetime
- 1998-05-22 BR BRPI9809153-0 patent/BRPI9809153B8/pt not_active IP Right Cessation
- 1998-05-22 DE DE69820435T patent/DE69820435T2/de not_active Expired - Lifetime
- 1998-05-22 IL IL13310098A patent/IL133100A/en not_active IP Right Cessation
- 1998-05-22 AU AU75407/98A patent/AU725565B2/en not_active Ceased
- 1998-05-22 KR KR1019997010757A patent/KR100543856B1/ko not_active IP Right Cessation
- 1998-05-22 CA CA002290544A patent/CA2290544A1/en not_active Abandoned
- 1998-05-22 CZ CZ0417199A patent/CZ297243B6/cs not_active IP Right Cessation
- 1998-05-22 PT PT98922947T patent/PT983230E/pt unknown
- 1998-05-22 AT AT98922947T patent/ATE256101T1/de active
- 1998-05-22 HU HU0003637A patent/HU224128B1/hu active IP Right Grant
- 1998-05-22 PL PL336848A patent/PL190905B1/pl unknown
-
1999
- 1999-11-12 US US09/438,385 patent/US6337422B1/en not_active Expired - Lifetime
- 1999-11-19 NO NO19995676A patent/NO327490B1/no not_active IP Right Cessation
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5321137A (en) * | 1976-06-11 | 1978-02-27 | Serukapeto | Xxray contrast medium |
JPS55129298A (en) * | 1979-03-23 | 1980-10-06 | Mallinckrodt Chemical Works | N*n**bis*2*33dihydroxypropyl**2*4*66triiodoo 55*22ketoollgulonamido*isophthalamide and irridiative composition containing it |
JPS58131970A (ja) * | 1982-01-11 | 1983-08-06 | マリンクロツド・インコ−ポレイテツド | X線造影剤 |
JPH03504124A (ja) * | 1988-03-01 | 1991-09-12 | マリンクロット,インコーポレイテッド | 非イオン性x線コントラスト剤、組成物及び方法 |
JPH06506954A (ja) * | 1991-04-16 | 1994-08-04 | マリンクロッド・メディカル・インコーポレイテッド | 5−アミノ−n,n’−ビス(2,3−ジヒドロキシプロピル)−2,4,6−トリヨードイソフタルアミドの乾燥における共沸蒸留の使用 |
JPH10505856A (ja) * | 1994-09-23 | 1998-06-09 | ニコムド イメージング エイエス | ヨウ素化x線コントラスト媒体 |
JPH11505827A (ja) * | 1995-05-24 | 1999-05-25 | ナイコムド イメージング エーエス | ヨウ素化方法 |
Also Published As
Publication number | Publication date |
---|---|
AU7540798A (en) | 1998-12-11 |
GB9710726D0 (en) | 1997-07-16 |
CZ417199A3 (cs) | 2000-05-17 |
PL190905B1 (pl) | 2006-02-28 |
PL336848A1 (en) | 2000-07-17 |
KR20010012794A (ko) | 2001-02-26 |
IL133100A (en) | 2004-07-25 |
DE69820435D1 (en) | 2004-01-22 |
BRPI9809153A (pt) | 2000-08-01 |
CN1257479A (zh) | 2000-06-21 |
AU725565B2 (en) | 2000-10-12 |
HUP0003637A1 (hu) | 2001-02-28 |
IL133100A0 (en) | 2001-03-19 |
NO995676D0 (no) | 1999-11-19 |
CN1161324C (zh) | 2004-08-11 |
BRPI9809153B1 (pt) | 2017-11-14 |
EP0983230B1 (en) | 2003-12-10 |
EP0983230A1 (en) | 2000-03-08 |
KR100543856B1 (ko) | 2006-01-23 |
HUP0003637A3 (en) | 2001-06-28 |
NO995676L (no) | 1999-11-19 |
DE69820435T2 (de) | 2004-10-07 |
US6337422B1 (en) | 2002-01-08 |
WO1998052911A1 (en) | 1998-11-26 |
JP4476366B2 (ja) | 2010-06-09 |
CZ297243B6 (cs) | 2006-10-11 |
CA2290544A1 (en) | 1998-11-26 |
HU224128B1 (hu) | 2005-05-30 |
BRPI9809153B8 (pt) | 2021-07-06 |
ATE256101T1 (de) | 2003-12-15 |
NO327490B1 (no) | 2009-07-13 |
PT983230E (pt) | 2004-04-30 |
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