SK8897A3 - Process for the preparation of s-(-)-5-££2-(acetoxy)-1- -oxopropyl|amino|-2,4,6-triiodine-1,3-benzenedicarboxylic acid dichloride - Google Patents
Process for the preparation of s-(-)-5-££2-(acetoxy)-1- -oxopropyl|amino|-2,4,6-triiodine-1,3-benzenedicarboxylic acid dichloride Download PDFInfo
- Publication number
- SK8897A3 SK8897A3 SK88-97A SK8897A SK8897A3 SK 8897 A3 SK8897 A3 SK 8897A3 SK 8897 A SK8897 A SK 8897A SK 8897 A3 SK8897 A3 SK 8897A3
- Authority
- SK
- Slovakia
- Prior art keywords
- amino
- triiodo
- benzenedicarboxylic acid
- acetyloxy
- oxopropyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 28
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 title description 2
- 239000002904 solvent Substances 0.000 claims abstract description 30
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- 239000002253 acid Substances 0.000 claims abstract description 8
- 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 abstract description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 32
- 239000000243 solution Substances 0.000 claims description 29
- 239000011541 reaction mixture Substances 0.000 claims description 21
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 15
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 14
- 238000000746 purification Methods 0.000 claims description 13
- 238000002955 isolation Methods 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- 239000003085 diluting agent Substances 0.000 claims description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 5
- 238000001556 precipitation Methods 0.000 claims description 5
- KBZFDRWPMZESDI-UHFFFAOYSA-N 5-aminobenzene-1,3-dicarboxylic acid Chemical compound NC1=CC(C(O)=O)=CC(C(O)=O)=C1 KBZFDRWPMZESDI-UHFFFAOYSA-N 0.000 claims description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 4
- XMMFBEWONDCTLD-UHFFFAOYSA-N acetyl(dimethyl)azanium;chloride Chemical compound Cl.CN(C)C(C)=O XMMFBEWONDCTLD-UHFFFAOYSA-N 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 238000000605 extraction Methods 0.000 claims description 4
- 230000003287 optical effect Effects 0.000 claims description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 4
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
- 238000007865 diluting Methods 0.000 claims description 3
- 239000007789 gas Substances 0.000 claims description 3
- NBDAHKQJXVLAID-UHFFFAOYSA-N 5-nitroisophthalic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC([N+]([O-])=O)=C1 NBDAHKQJXVLAID-UHFFFAOYSA-N 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- IUEVXLACZFKZSP-UHFFFAOYSA-L disodium;5-aminobenzene-1,3-dicarboxylate Chemical compound [Na+].[Na+].NC1=CC(C([O-])=O)=CC(C([O-])=O)=C1 IUEVXLACZFKZSP-UHFFFAOYSA-L 0.000 claims description 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 238000005192 partition Methods 0.000 claims description 2
- 229940090181 propyl acetate Drugs 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 159000000000 sodium salts Chemical class 0.000 claims description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims 2
- WJXXCTSBMNYHHS-UHFFFAOYSA-N 5-aminobenzene-1,3-dicarbonyl chloride Chemical compound NC1=CC(C(Cl)=O)=CC(C(Cl)=O)=C1 WJXXCTSBMNYHHS-UHFFFAOYSA-N 0.000 claims 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 claims 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
- 150000002168 ethanoic acid esters Chemical class 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 239000012433 hydrogen halide Substances 0.000 claims 1
- 229910000039 hydrogen halide Inorganic materials 0.000 claims 1
- 230000002083 iodinating effect Effects 0.000 claims 1
- 230000007935 neutral effect Effects 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 abstract 1
- 239000000047 product Substances 0.000 description 37
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 238000003756 stirring Methods 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 238000009413 insulation Methods 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229940126062 Compound A Drugs 0.000 description 2
- 230000005526 G1 to G0 transition Effects 0.000 description 2
- 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 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000000825 ultraviolet detection Methods 0.000 description 2
- NAMDIHYPBYVYAP-UHFFFAOYSA-N 1-methoxy-2-(2-methoxyethoxy)ethane Chemical compound COCCOCCOC.COCCOCCOC NAMDIHYPBYVYAP-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 229910006124 SOCl2 Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- RGXHKACZQXJQIC-UHFFFAOYSA-N [1-[3-carbamoyl-5-(1,3-dihydroxypropan-2-ylcarbamoyl)-2,4,6-triiodoanilino]-1-oxopropan-2-yl] acetate Chemical compound CC(=O)OC(C)C(=O)NC1=C(I)C(C(N)=O)=C(I)C(C(=O)NC(CO)CO)=C1I RGXHKACZQXJQIC-UHFFFAOYSA-N 0.000 description 1
- GFTWDQJSZPFMOZ-UHFFFAOYSA-N acetyl acetate Chemical compound CC(=O)OC(C)=O.CC(=O)OC(C)=O GFTWDQJSZPFMOZ-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 239000002872 contrast media Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- BONORRGKLJBGRV-UHFFFAOYSA-N methapyrilene hydrochloride Chemical group Cl.C=1C=CC=NC=1N(CCN(C)C)CC1=CC=CS1 BONORRGKLJBGRV-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229940094933 n-dodecane Drugs 0.000 description 1
- 230000002572 peristaltic effect Effects 0.000 description 1
- 239000002279 physical standard Substances 0.000 description 1
- YYFIGOPUHPDIBO-UHFFFAOYSA-N propanoic acid;hydrochloride Chemical compound Cl.CCC(O)=O YYFIGOPUHPDIBO-UHFFFAOYSA-N 0.000 description 1
- 230000010349 pulsation Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Polyamides (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI951048A IT1274550B (it) | 1995-05-23 | 1995-05-23 | Processo per la preparazione del dicloruro dell'acido s-5-¬¬2- (acetilossi)-1-ossopropil|ammino|-2,4,6-triiodo-1,3- benzendicarbossilico |
| ITRM950548 IT1281319B1 (it) | 1995-08-04 | 1995-08-04 | Procedimento per la preparazione di dicloruro dell'acido s-5-<<2- (acetilossi)-1-ossopropil>ammino>-2,4,6-triiodo-1,3-benzendi- |
| PCT/EP1996/002104 WO1996037460A1 (en) | 1995-05-23 | 1996-05-17 | Process for the preparation of a dicarboxylic acid dichloride |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK8897A3 true SK8897A3 (en) | 1997-08-06 |
Family
ID=26331280
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK88-97A SK8897A3 (en) | 1995-05-23 | 1996-05-17 | Process for the preparation of s-(-)-5-££2-(acetoxy)-1- -oxopropyl|amino|-2,4,6-triiodine-1,3-benzenedicarboxylic acid dichloride |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US5672735A (de) |
| EP (1) | EP0773925B1 (de) |
| JP (2) | JP4012567B2 (de) |
| KR (1) | KR100269080B1 (de) |
| CN (1) | CN1068582C (de) |
| AT (1) | ATE189674T1 (de) |
| AU (1) | AU698623B2 (de) |
| BR (1) | BR9606394A (de) |
| CA (1) | CA2195634C (de) |
| CZ (1) | CZ290363B6 (de) |
| DE (2) | DE773925T1 (de) |
| ES (1) | ES2103253T3 (de) |
| GR (1) | GR970300028T1 (de) |
| HU (1) | HU216537B (de) |
| IL (1) | IL118358A (de) |
| NO (1) | NO313697B1 (de) |
| PL (1) | PL187308B1 (de) |
| PT (1) | PT773925E (de) |
| SI (1) | SI9620010B (de) |
| SK (1) | SK8897A3 (de) |
| WO (1) | WO1996037460A1 (de) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1289521B1 (it) * | 1996-12-24 | 1998-10-15 | Zambon Spa | Processo per la purificazione di un intermedio |
| IT1289520B1 (it) * | 1996-12-24 | 1998-10-15 | Zambon Spa | Processo per la preparazione di un intermedio utile nella sintesi di mezzi di contrasto iodurati |
| IT1289519B1 (it) * | 1996-12-24 | 1998-10-15 | Zambon Spa | Processo per la preparazione di un intermedio utile nella sintesi di mezzi di contrasto iodurati |
| EP2230227A1 (de) | 2009-03-20 | 2010-09-22 | Bracco Imaging S.p.A | Verfahren zur Herstellung von aromatischen Trijodid-Carboxyl- Derivaten |
| EP2243767A1 (de) | 2009-04-21 | 2010-10-27 | Bracco Imaging S.p.A | Verfahren zur Iodierung aromatischer Verbindungen |
| PT105770B (pt) * | 2011-06-24 | 2013-07-08 | Hovione Farmaciencia S A | Novo intermediário e seu uso na preparação de agente de contrate triiodado |
| WO2014090650A1 (en) * | 2012-12-11 | 2014-06-19 | Bracco Imaging Spa | Continuous process for the preparation of (s)-2-acetyloxypropionic acid chloride |
| MX2016005829A (es) | 2013-11-05 | 2017-03-10 | Bracco Imaging Spa | Procedimiento para la preparacion de iopamidol. |
| CN106458830B (zh) | 2014-06-10 | 2019-03-05 | 伯拉考成像股份公司 | 制备(s)-2-乙酰氧基丙酸及其衍生物的方法 |
| CN110023279B (zh) | 2016-12-05 | 2022-03-11 | 伯拉考成像股份公司 | 放射照相剂中间体的机械化学合成 |
| FR3062850B1 (fr) | 2017-02-10 | 2020-01-31 | Guerbet | Procede de preparation monotope de composes organo-iodes |
| FR3084668A1 (fr) | 2018-08-02 | 2020-02-07 | Guerbet | Procede de preparation monotope de composes organo-iodes intermediaires a la synthese du ioversol |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH608189A5 (de) * | 1974-12-13 | 1978-12-29 | Savac Ag | |
| CH626873A5 (de) * | 1977-03-28 | 1981-12-15 | Bracco Ind Chimica Spa | |
| DE2909439A1 (de) * | 1979-03-08 | 1980-09-18 | Schering Ag | Neue nichtionische roentgenkontrastmittel |
| IT1256162B (it) * | 1992-10-27 | 1995-11-29 | Zambon Spa | Processo per la preparazione di un intermedio della sintesi organica |
| IT1274027B (it) * | 1994-03-03 | 1997-07-14 | Zambon Spa | Processo per la preparazione e purificazione di mezzi di contrasto iodurati |
-
1996
- 1996-05-17 CN CN96190525A patent/CN1068582C/zh not_active Expired - Lifetime
- 1996-05-17 AU AU58188/96A patent/AU698623B2/en not_active Expired
- 1996-05-17 ES ES96919778T patent/ES2103253T3/es not_active Expired - Lifetime
- 1996-05-17 CA CA002195634A patent/CA2195634C/en not_active Expired - Lifetime
- 1996-05-17 BR BR9606394A patent/BR9606394A/pt not_active Application Discontinuation
- 1996-05-17 PT PT96919778T patent/PT773925E/pt unknown
- 1996-05-17 CZ CZ1997186A patent/CZ290363B6/cs not_active IP Right Cessation
- 1996-05-17 DE DE0773925T patent/DE773925T1/de active Pending
- 1996-05-17 JP JP53534696A patent/JP4012567B2/ja not_active Expired - Lifetime
- 1996-05-17 HU HU9700190A patent/HU216537B/hu unknown
- 1996-05-17 AT AT96919778T patent/ATE189674T1/de not_active IP Right Cessation
- 1996-05-17 EP EP96919778A patent/EP0773925B1/de not_active Expired - Lifetime
- 1996-05-17 WO PCT/EP1996/002104 patent/WO1996037460A1/en active IP Right Grant
- 1996-05-17 PL PL96318284A patent/PL187308B1/pl unknown
- 1996-05-17 KR KR1019970700403A patent/KR100269080B1/ko not_active IP Right Cessation
- 1996-05-17 DE DE69606601T patent/DE69606601T2/de not_active Expired - Lifetime
- 1996-05-17 SI SI9620010A patent/SI9620010B/sl unknown
- 1996-05-17 SK SK88-97A patent/SK8897A3/sk unknown
- 1996-05-21 US US08/651,474 patent/US5672735A/en not_active Expired - Lifetime
- 1996-05-22 IL IL11835896A patent/IL118358A/xx not_active IP Right Cessation
-
1997
- 1997-01-21 NO NO19970262A patent/NO313697B1/no not_active IP Right Cessation
- 1997-09-30 GR GR970300028T patent/GR970300028T1/el unknown
-
2007
- 2007-06-19 JP JP2007160804A patent/JP4675355B2/ja not_active Expired - Lifetime
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