SK8797A3 - Process for the preparation of 5-amino-2,4,6-triiodine-1,3- -benzenedicarboxylic acid dichloride - Google Patents
Process for the preparation of 5-amino-2,4,6-triiodine-1,3- -benzenedicarboxylic acid dichloride Download PDFInfo
- Publication number
- SK8797A3 SK8797A3 SK87-97A SK8797A SK8797A3 SK 8797 A3 SK8797 A3 SK 8797A3 SK 8797 A SK8797 A SK 8797A SK 8797 A3 SK8797 A3 SK 8797A3
- Authority
- SK
- Slovakia
- Prior art keywords
- amino
- benzenedicarboxylic acid
- acid
- triiodo
- hydrocarbon
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 39
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims abstract description 25
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims abstract description 25
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 17
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 17
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims abstract description 16
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims abstract description 12
- 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 abstract description 8
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 8
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000002904 solvent Substances 0.000 claims abstract description 7
- 150000003512 tertiary amines Chemical class 0.000 claims abstract description 5
- 230000003197 catalytic effect Effects 0.000 claims abstract description 3
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 40
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 38
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims description 38
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims description 33
- 239000002253 acid Substances 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- 239000000243 solution Substances 0.000 claims description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- 239000004215 Carbon black (E152) Substances 0.000 claims description 8
- 238000005660 chlorination reaction Methods 0.000 claims description 6
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 6
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 6
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 4
- 229940094933 n-dodecane Drugs 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- FVIAPYQJXFVGHJ-UHFFFAOYSA-N 2,4,6-triiodo-5-(sulfinylamino)benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=C(I)C(N=S=O)=C(I)C(C(Cl)=O)=C1I FVIAPYQJXFVGHJ-UHFFFAOYSA-N 0.000 claims description 3
- COHDGTRFTKHYSJ-UHFFFAOYSA-N 2-Ethyl-5-methylpyridine Chemical compound CCC1=CC=C(C)C=N1 COHDGTRFTKHYSJ-UHFFFAOYSA-N 0.000 claims description 3
- KBZFDRWPMZESDI-UHFFFAOYSA-N 5-aminobenzene-1,3-dicarboxylic acid Chemical class NC1=CC(C(O)=O)=CC(C(O)=O)=C1 KBZFDRWPMZESDI-UHFFFAOYSA-N 0.000 claims description 3
- 239000003350 kerosene 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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 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
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 claims description 2
- JEDHEXUPBRMUMB-UHFFFAOYSA-N n,n-dimethylpyridin-3-amine Chemical compound CN(C)C1=CC=CN=C1 JEDHEXUPBRMUMB-UHFFFAOYSA-N 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- 239000012266 salt solution Substances 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 235000011149 sulphuric acid Nutrition 0.000 claims description 2
- 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
- YHYITPYNGUZSNF-UHFFFAOYSA-N O=C(C1=CC(C(Cl)=O)=CC=C1)Cl.Cl.Cl Chemical compound O=C(C1=CC(C(Cl)=O)=CC=C1)Cl.Cl.Cl YHYITPYNGUZSNF-UHFFFAOYSA-N 0.000 claims 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
- -1 dichloride 2,4,6-triiodo-1,3-benzenedicarboxylic acid Chemical compound 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 230000026045 iodination Effects 0.000 claims 1
- 238000006192 iodination reaction Methods 0.000 claims 1
- 230000007935 neutral effect Effects 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 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 abstract description 21
- 239000000047 product Substances 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 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
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229910006124 SOCl2 Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 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
- IPHVGAPABXWWLO-UHFFFAOYSA-N 2,4,6-triiodobenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=C(I)C=C(I)C(C(O)=O)=C1I IPHVGAPABXWWLO-UHFFFAOYSA-N 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 150000001555 benzenes Chemical group 0.000 description 1
- LSDKXERJHVJDEO-UHFFFAOYSA-N butyl acetate;hydrochloride Chemical compound Cl.CCCCOC(C)=O LSDKXERJHVJDEO-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 239000002872 contrast media Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 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
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 238000000825 ultraviolet detection Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
- C07C381/10—Compounds containing sulfur atoms doubly-bound to nitrogen atoms
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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI951044A IT1274546B (it) | 1995-05-23 | 1995-05-23 | Processo per la preparazione del dicloruro dell'acido 5-ammino-2,4,- 6-triiodoisoftalico |
| ITRM950550 IT1281320B1 (it) | 1995-08-04 | 1995-08-04 | Procedimento di preparazione di dicloruro dell'acido 5-ammino-2,4,6- triiodo-1,3-benzendicarbossilico per reazione dell'acido |
| PCT/EP1996/002103 WO1996037459A1 (en) | 1995-05-23 | 1996-05-17 | Process for the preparation of a dicarboxylic acid dichloride |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK8797A3 true SK8797A3 (en) | 1997-08-06 |
Family
ID=26331277
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK87-97A SK8797A3 (en) | 1995-05-23 | 1996-05-17 | Process for the preparation of 5-amino-2,4,6-triiodine-1,3- -benzenedicarboxylic acid dichloride |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US5616795A (zh) |
| EP (1) | EP0773924B1 (zh) |
| JP (1) | JP4012566B2 (zh) |
| KR (1) | KR100255914B1 (zh) |
| CN (1) | CN1157367C (zh) |
| AT (1) | ATE176663T1 (zh) |
| AU (1) | AU702895B2 (zh) |
| BR (1) | BR9606488A (zh) |
| CA (1) | CA2195636C (zh) |
| CZ (1) | CZ290345B6 (zh) |
| DE (2) | DE69601525T2 (zh) |
| DK (1) | DK0773924T3 (zh) |
| ES (1) | ES2103252T3 (zh) |
| GR (1) | GR970300027T1 (zh) |
| HU (1) | HU216548B (zh) |
| IL (1) | IL118359A (zh) |
| MX (1) | MX9700548A (zh) |
| NO (1) | NO313696B1 (zh) |
| PL (1) | PL182447B1 (zh) |
| SI (1) | SI9620012A (zh) |
| SK (1) | SK8797A3 (zh) |
| WO (1) | WO1996037459A1 (zh) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1271107B (it) * | 1994-11-29 | 1997-05-26 | Zambon Spa | Processo per la preparazione di un intermedio utile nella sintesi di composti organici |
| IT1292037B1 (it) * | 1997-05-30 | 1999-01-25 | Bracco Spa | Processo per la preparazione di 5-(acetil 62,3-diidrossipropil)- ammino)-n,n'-bis(2,3-diidrossipropil)-2,4,6-triiodo-1,3-benzen- |
| WO2007073202A1 (en) | 2005-12-19 | 2007-06-28 | Ge Healthcare As | Purification process of iodixanol |
| GB0717189D0 (en) * | 2007-09-04 | 2007-10-17 | Syngenta Participations Ag | Novel processes and compounds |
| US8445725B2 (en) * | 2008-01-14 | 2013-05-21 | Mallinckrodt Llc | Process for the preparation of iosimenol |
| EP2230227A1 (en) * | 2009-03-20 | 2010-09-22 | Bracco Imaging S.p.A | Process for the preparation of triiodinated carboxylic aromatic derivatives |
| EP2243767A1 (en) * | 2009-04-21 | 2010-10-27 | Bracco Imaging S.p.A | Process for the iodination of aromatic compounds |
| US7999134B2 (en) | 2009-07-21 | 2011-08-16 | Ge Healthcare As | Crystallization of iodixanol using milling |
| US7999135B2 (en) | 2009-07-21 | 2011-08-16 | Ge Healthcare As | Crystallization of iodixanol using ultrasound |
| AU2009355814B2 (en) | 2009-11-26 | 2016-06-30 | Imax Diagnostic Imaging Holding Ltd | Preparation and purification of iodixanol |
| EP2394984A1 (en) | 2010-06-10 | 2011-12-14 | Bracco Imaging S.p.A | Process for the iodination of phenolic derivatives |
| EP2931696B1 (en) | 2012-12-11 | 2018-08-22 | Bracco Imaging S.p.A | Continuous process for the preparation of (s)-2-acetyloxypropionic acid |
| LT3066071T (lt) | 2013-11-05 | 2018-09-10 | Bracco Imaging S.P.A. | Jopamidolio gamybos būdas |
| CA2949433C (en) | 2014-06-10 | 2022-05-03 | Bracco Imaging Spa | Method for the preparation of (s)-2-acetyloxypropionic acid and derivatives thereof |
| CN104230731B (zh) * | 2014-09-24 | 2016-01-20 | 武汉理工大学 | 造影剂中间体三碘异酞酰氯的制备方法 |
| WO2018104228A1 (en) | 2016-12-05 | 2018-06-14 | Bracco Imaging Spa | Mechanochemical synthesis of radiographic agents intermediates |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH608189A5 (zh) * | 1974-12-13 | 1978-12-29 | Savac Ag | |
| 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 |
| IT1207226B (it) * | 1979-08-09 | 1989-05-17 | Bracco Ind Chimica Spa | Derivati dell'acido 2,4,6-triiodo-isoftalico, metodo per la loro preparazione e mezzi di contrasto che li contengono. |
| US4396598A (en) * | 1982-01-11 | 1983-08-02 | Mallinckrodt, Inc. | Triiodoisophthalamide X-ray contrast agent |
| FR2541676A1 (fr) * | 1983-02-25 | 1984-08-31 | Guerbet Sa | Composes non-ioniques a structures benzenique iodee ou bromee et produits opacifiants en contenant |
| US5191120A (en) * | 1989-12-13 | 1993-03-02 | Mallinckrodt Medical, Inc. | Process for preparing nonionic X-ray contrast agents |
| US5075502A (en) * | 1989-12-13 | 1991-12-24 | Mallinckrodt, Inc. | Nonionic x-ray contrast agents, compositions and methods |
| IT1271107B (it) * | 1994-11-29 | 1997-05-26 | Zambon Spa | Processo per la preparazione di un intermedio utile nella sintesi di composti organici |
-
1996
- 1996-05-17 KR KR1019970700402A patent/KR100255914B1/ko not_active IP Right Cessation
- 1996-05-17 DE DE69601525T patent/DE69601525T2/de not_active Expired - Lifetime
- 1996-05-17 SK SK87-97A patent/SK8797A3/sk unknown
- 1996-05-17 CA CA002195636A patent/CA2195636C/en not_active Expired - Lifetime
- 1996-05-17 EP EP96916098A patent/EP0773924B1/en not_active Expired - Lifetime
- 1996-05-17 CZ CZ1997187A patent/CZ290345B6/cs not_active IP Right Cessation
- 1996-05-17 ES ES96916098T patent/ES2103252T3/es not_active Expired - Lifetime
- 1996-05-17 US US08/650,094 patent/US5616795A/en not_active Expired - Lifetime
- 1996-05-17 DE DE0773924T patent/DE773924T1/de active Pending
- 1996-05-17 WO PCT/EP1996/002103 patent/WO1996037459A1/en active IP Right Grant
- 1996-05-17 AU AU58978/96A patent/AU702895B2/en not_active Expired
- 1996-05-17 HU HU9700188A patent/HU216548B/hu unknown
- 1996-05-17 JP JP53534596A patent/JP4012566B2/ja not_active Expired - Lifetime
- 1996-05-17 AT AT96916098T patent/ATE176663T1/de active
- 1996-05-17 SI SI9620012A patent/SI9620012A/sl unknown
- 1996-05-17 PL PL96318311A patent/PL182447B1/pl unknown
- 1996-05-17 DK DK96916098T patent/DK0773924T3/da active
- 1996-05-17 MX MX9700548A patent/MX9700548A/es unknown
- 1996-05-17 BR BR9606488A patent/BR9606488A/pt not_active Application Discontinuation
- 1996-05-17 CN CNB961905271A patent/CN1157367C/zh not_active Expired - Lifetime
- 1996-05-22 IL IL11835996A patent/IL118359A/xx not_active IP Right Cessation
-
1997
- 1997-01-21 NO NO19970261A patent/NO313696B1/no not_active IP Right Cessation
- 1997-09-30 GR GR970300027T patent/GR970300027T1/el unknown
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