NO324342B1 - Fremgangsmate ved fremstilling av (S)-N, N'-bis((2-hydroksy-1-(hydroksymetyl)etyl)-5-((2-hydroksy-1-oksopropyl)amino)-2,4,6-trijod-1,3-benzendikarboksamid - Google Patents
Fremgangsmate ved fremstilling av (S)-N, N'-bis((2-hydroksy-1-(hydroksymetyl)etyl)-5-((2-hydroksy-1-oksopropyl)amino)-2,4,6-trijod-1,3-benzendikarboksamid Download PDFInfo
- Publication number
- NO324342B1 NO324342B1 NO19980594A NO980594A NO324342B1 NO 324342 B1 NO324342 B1 NO 324342B1 NO 19980594 A NO19980594 A NO 19980594A NO 980594 A NO980594 A NO 980594A NO 324342 B1 NO324342 B1 NO 324342B1
- Authority
- NO
- Norway
- Prior art keywords
- resins
- resin
- bed
- anionic
- hydroxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 36
- 238000002360 preparation method Methods 0.000 title claims description 7
- MCZYFQHMXGCFDR-UHFFFAOYSA-N 3-n-(1,3-dihydroxypropan-2-yl)-5-(2-hydroxypropanoylamino)-2,4,6-triiodobenzene-1,3-dicarboxamide Chemical compound CC(O)C(=O)NC1=C(I)C(C(N)=O)=C(I)C(C(=O)NC(CO)CO)=C1I MCZYFQHMXGCFDR-UHFFFAOYSA-N 0.000 title 1
- 229920005989 resin Polymers 0.000 claims abstract description 85
- 239000011347 resin Substances 0.000 claims abstract description 85
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- 238000006243 chemical reaction Methods 0.000 claims abstract description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 7
- GMPOMLNJZPYPGR-VKHMYHEASA-N [(2s)-1-(3,5-dicarbonochloridoyl-2,4,6-triiodoanilino)-1-oxopropan-2-yl] acetate Chemical compound CC(=O)O[C@@H](C)C(=O)NC1=C(I)C(C(Cl)=O)=C(I)C(C(Cl)=O)=C1I GMPOMLNJZPYPGR-VKHMYHEASA-N 0.000 claims abstract description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 39
- 125000000129 anionic group Chemical group 0.000 claims description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 32
- 239000002904 solvent Substances 0.000 claims description 17
- 125000002091 cationic group Chemical group 0.000 claims description 15
- KJJPLEZQSCZCKE-UHFFFAOYSA-N 2-aminopropane-1,3-diol Chemical compound OCC(N)CO KJJPLEZQSCZCKE-UHFFFAOYSA-N 0.000 claims description 12
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 11
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 claims description 10
- 230000007062 hydrolysis Effects 0.000 claims description 9
- 238000006460 hydrolysis reaction Methods 0.000 claims description 9
- 230000008030 elimination Effects 0.000 claims description 6
- 238000003379 elimination reaction Methods 0.000 claims description 6
- 238000010828 elution Methods 0.000 claims description 6
- 238000005188 flotation Methods 0.000 claims description 6
- 239000012458 free base Substances 0.000 claims description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- 125000005395 methacrylic acid group Chemical group 0.000 claims description 3
- 229920000642 polymer Polymers 0.000 claims description 3
- 159000000000 sodium salts Chemical group 0.000 claims description 3
- FBJVWRITWDYUAC-UHFFFAOYSA-N 5-amino-2,4,6-triiodobenzene-1,3-dicarbonyl chloride Chemical compound NC1=C(I)C(C(Cl)=O)=C(I)C(C(Cl)=O)=C1I FBJVWRITWDYUAC-UHFFFAOYSA-N 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 238000005292 vacuum distillation Methods 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 8
- 238000003786 synthesis reaction Methods 0.000 abstract description 7
- 238000002955 isolation Methods 0.000 abstract description 6
- 239000002253 acid Substances 0.000 abstract description 4
- 238000011097 chromatography purification Methods 0.000 abstract description 3
- 230000003449 preventive effect Effects 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 238000011084 recovery Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 9
- 239000006227 byproduct Substances 0.000 description 6
- 239000012045 crude solution Substances 0.000 description 6
- 229920001429 chelating resin Polymers 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 150000001805 chlorine compounds Chemical class 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 101100412856 Mus musculus Rhod gene Proteins 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- 239000002872 contrast media Substances 0.000 description 2
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- -1 two luen Chemical compound 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- BHKKSKOHRFHHIN-MRVPVSSYSA-N 1-[[2-[(1R)-1-aminoethyl]-4-chlorophenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound N[C@H](C)C1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC(=C1)Cl BHKKSKOHRFHHIN-MRVPVSSYSA-N 0.000 description 1
- ZMZGFLUUZLELNE-UHFFFAOYSA-N 2,3,5-triiodobenzoic acid Chemical compound OC(=O)C1=CC(I)=CC(I)=C1I ZMZGFLUUZLELNE-UHFFFAOYSA-N 0.000 description 1
- LNFVLJQCPHHJBO-UHFFFAOYSA-N 2,4,6-triiodobenzene-1,3-dicarboxamide Chemical compound NC(=O)C1=C(I)C=C(I)C(C(N)=O)=C1I LNFVLJQCPHHJBO-UHFFFAOYSA-N 0.000 description 1
- HNPVERUJGFNNRV-UHFFFAOYSA-N 3-iodophthalic acid Chemical class OC(=O)C1=CC=CC(I)=C1C(O)=O HNPVERUJGFNNRV-UHFFFAOYSA-N 0.000 description 1
- GOCIYSIBXXQUAW-REOHCLBHSA-N 5-[[(2s)-2-hydroxypropanoyl]amino]-2,4,6-triiodobenzene-1,3-dicarboxylic acid Chemical compound C[C@H](O)C(=O)NC1=C(I)C(C(O)=O)=C(I)C(C(O)=O)=C1I GOCIYSIBXXQUAW-REOHCLBHSA-N 0.000 description 1
- JEZJSNULLBSYHV-UHFFFAOYSA-N 5-amino-2,4,6-triiodobenzene-1,3-dicarboxylic acid Chemical compound NC1=C(I)C(C(O)=O)=C(I)C(C(O)=O)=C1I JEZJSNULLBSYHV-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940072049 amyl acetate Drugs 0.000 description 1
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
- 229960004365 benzoic acid Drugs 0.000 description 1
- 229940043232 butyl acetate Drugs 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000011033 desalting Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- 229940093499 ethyl acetate Drugs 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910001504 inorganic chloride Inorganic materials 0.000 description 1
- 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 1
- 229960004647 iopamidol Drugs 0.000 description 1
- 229940117955 isoamyl acetate Drugs 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/22—Separation; Purification; Stabilisation; Use of additives
- C07C231/24—Separation; Purification
-
- 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
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT96MI001204A IT1288114B1 (it) | 1996-06-13 | 1996-06-13 | Processo per la purificazione di un intermedio |
| PCT/EP1997/003021 WO1997047590A2 (fr) | 1996-06-13 | 1997-06-11 | Procede de purification d'un intermediaire dans la preparation de l'iopamidol |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO980594D0 NO980594D0 (no) | 1998-02-11 |
| NO980594L NO980594L (no) | 1998-04-07 |
| NO324342B1 true NO324342B1 (no) | 2007-09-24 |
Family
ID=11374420
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19980594A NO324342B1 (no) | 1996-06-13 | 1998-02-11 | Fremgangsmate ved fremstilling av (S)-N, N'-bis((2-hydroksy-1-(hydroksymetyl)etyl)-5-((2-hydroksy-1-oksopropyl)amino)-2,4,6-trijod-1,3-benzendikarboksamid |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US5849953A (fr) |
| EP (1) | EP0851854B1 (fr) |
| JP (1) | JP4018751B2 (fr) |
| CN (1) | CN1089335C (fr) |
| AT (1) | ATE210630T1 (fr) |
| AU (1) | AU3094597A (fr) |
| CZ (1) | CZ293956B6 (fr) |
| DE (1) | DE69709044T2 (fr) |
| ES (1) | ES2165610T3 (fr) |
| HU (1) | HU227980B1 (fr) |
| IL (1) | IL123259A (fr) |
| IN (1) | IN182809B (fr) |
| IT (1) | IT1288114B1 (fr) |
| NO (1) | NO324342B1 (fr) |
| PT (1) | PT851854E (fr) |
| WO (1) | WO1997047590A2 (fr) |
| ZA (1) | ZA975203B (fr) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1299202B1 (it) * | 1998-05-08 | 2000-02-29 | Dibra Spa | Processo per la preparazione della s-n,n'-bis (2-idrossi-1- (idrossimetil)etil) -5-((2-idrossi-1-ossopropil)ammino)-2,4,6-triiodo |
| IT1302200B1 (it) * | 1998-09-11 | 2000-07-31 | Dibra Spa | PROCESSO PER LA PREPARAZIONE DELLA S-N,N'-BIS°2-IDROSSI-1-(IDROSSIMETIL)ETILé-5-°(2-IDROSSI-1- |
| DE102007053531B4 (de) * | 2007-11-09 | 2010-10-21 | Hs Genion Gmbh | Rolloeinrichtung |
| EP2230227A1 (fr) | 2009-03-20 | 2010-09-22 | Bracco Imaging S.p.A | Procédé de préparation de dérivés aromatiques carboxyliques tri-iodés |
| EP2243767A1 (fr) | 2009-04-21 | 2010-10-27 | Bracco Imaging S.p.A | Procédé d'iodation de composés aromatiques |
| IT1403988B1 (it) * | 2010-07-15 | 2013-11-08 | Bracco Imaging Spa | Processo per la preparazione di agenti di contrasto. |
| KR102044772B1 (ko) | 2012-12-11 | 2019-11-14 | 브라코 이미징 에스.피.에이. | (s)-2-아세틸옥시프로피온산 클로라이드의 제조를 위한 연속식 공정 |
| CA3001399C (fr) | 2013-11-05 | 2020-06-30 | Bracco Imaging Spa | Procede de preparation d'iopamidol |
| LT3154928T (lt) | 2014-06-10 | 2020-05-11 | Bracco Imaging S.P.A. | (s)-2-acetiloksipropioninės rūgšties ir jos darinių gavimo būdas |
| PT108524B (pt) * | 2015-06-02 | 2017-12-15 | Hovione Farmaciência S A | Processo para a preparação de intermediários úteis na preparação de agentes de contraste não-iónicos |
| WO2018104228A1 (fr) | 2016-12-05 | 2018-06-14 | Bracco Imaging Spa | Synthèse mécanochimique d'intermédiaires d'agents radiographiques |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3324107A (en) * | 1964-03-27 | 1967-06-06 | Du Pont | Dialkylamide purification |
| US3576870A (en) * | 1967-07-05 | 1971-04-27 | Du Pont | Process for purifying n,n-dimethylacetamide |
| CH608189A5 (fr) * | 1974-12-13 | 1978-12-29 | Savac Ag | |
| CH616403A5 (en) * | 1975-10-29 | 1980-03-31 | Bracco Ind Chimica Spa | Process for the preparation of 2,4,6-triodoisophthalamides which are readily soluble in water. |
| IT1193211B (it) * | 1979-08-09 | 1988-06-15 | Bracco Ind Chimica Spa | Derivati dell'acido 2,4,6-triiodo-isoftalico,metodo per la loro preparazione e mezzi di contrasto che li contengono |
| GB2088850B (en) * | 1980-12-09 | 1983-09-28 | Coal Industry Patents Ltd | Treatment of n-methyl pyrrolidone |
| IT1256162B (it) * | 1992-10-27 | 1995-11-29 | Zambon Spa | Processo per la preparazione di un intermedio della sintesi organica |
-
1996
- 1996-06-13 IT IT96MI001204A patent/IT1288114B1/it active IP Right Grant
-
1997
- 1997-06-11 CZ CZ1998399A patent/CZ293956B6/cs not_active IP Right Cessation
- 1997-06-11 PT PT97925993T patent/PT851854E/pt unknown
- 1997-06-11 CN CN97190690A patent/CN1089335C/zh not_active Expired - Lifetime
- 1997-06-11 IL IL12325997A patent/IL123259A/xx not_active IP Right Cessation
- 1997-06-11 DE DE69709044T patent/DE69709044T2/de not_active Expired - Lifetime
- 1997-06-11 WO PCT/EP1997/003021 patent/WO1997047590A2/fr active IP Right Grant
- 1997-06-11 JP JP50119798A patent/JP4018751B2/ja not_active Expired - Lifetime
- 1997-06-11 AT AT97925993T patent/ATE210630T1/de not_active IP Right Cessation
- 1997-06-11 EP EP97925993A patent/EP0851854B1/fr not_active Expired - Lifetime
- 1997-06-11 ES ES97925993T patent/ES2165610T3/es not_active Expired - Lifetime
- 1997-06-11 AU AU30945/97A patent/AU3094597A/en not_active Abandoned
- 1997-06-11 HU HU9901631A patent/HU227980B1/hu unknown
- 1997-06-12 ZA ZA9705203A patent/ZA975203B/xx unknown
- 1997-06-12 US US08/873,771 patent/US5849953A/en not_active Expired - Lifetime
- 1997-06-13 IN IN1291MA1997 patent/IN182809B/en unknown
-
1998
- 1998-02-11 NO NO19980594A patent/NO324342B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ITMI961204A0 (fr) | 1996-06-13 |
| HUP9901631A3 (en) | 2001-02-28 |
| DE69709044T2 (de) | 2002-08-22 |
| IL123259A0 (en) | 1998-09-24 |
| NO980594D0 (no) | 1998-02-11 |
| JPH11510827A (ja) | 1999-09-21 |
| CZ293956B6 (cs) | 2004-08-18 |
| NO980594L (no) | 1998-04-07 |
| PT851854E (pt) | 2002-06-28 |
| CN1195338A (zh) | 1998-10-07 |
| ATE210630T1 (de) | 2001-12-15 |
| AU3094597A (en) | 1998-01-07 |
| EP0851854A2 (fr) | 1998-07-08 |
| ZA975203B (en) | 1998-01-20 |
| HU227980B1 (en) | 2012-07-30 |
| IN182809B (fr) | 1999-07-24 |
| JP4018751B2 (ja) | 2007-12-05 |
| HUP9901631A2 (hu) | 1999-08-30 |
| ITMI961204A1 (it) | 1997-12-13 |
| DE69709044D1 (de) | 2002-01-24 |
| IT1288114B1 (it) | 1998-09-10 |
| WO1997047590A2 (fr) | 1997-12-18 |
| US5849953A (en) | 1998-12-15 |
| ES2165610T3 (es) | 2002-03-16 |
| EP0851854B1 (fr) | 2001-12-12 |
| IL123259A (en) | 2000-07-16 |
| CN1089335C (zh) | 2002-08-21 |
| WO1997047590A3 (fr) | 1998-04-02 |
| CZ39998A3 (cs) | 1998-07-15 |
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