SI9620010B - Postopek za pripravo diklorida dikarboksilne kisline - Google Patents
Postopek za pripravo diklorida dikarboksilne kisline Download PDFInfo
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- SI9620010B SI9620010B SI9620010A SI9620010A SI9620010B SI 9620010 B SI9620010 B SI 9620010B SI 9620010 A SI9620010 A SI 9620010A SI 9620010 A SI9620010 A SI 9620010A SI 9620010 B SI9620010 B SI 9620010B
- Authority
- SI
- Slovenia
- Prior art keywords
- amino
- triiodo
- benzenedicarboxylic acid
- acetyloxy
- solvent
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract 19
- 238000002360 preparation method Methods 0.000 title claims abstract 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 title 1
- 239000002904 solvent Substances 0.000 claims abstract 16
- 239000002253 acid Substances 0.000 claims abstract 4
- 238000006243 chemical reaction Methods 0.000 claims abstract 4
- 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 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 12
- 238000000746 purification Methods 0.000 claims 9
- 238000002955 isolation Methods 0.000 claims 8
- 239000011541 reaction mixture Substances 0.000 claims 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 6
- 239000003085 diluting agent Substances 0.000 claims 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- 239000000243 solution Substances 0.000 claims 3
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims 2
- XMMFBEWONDCTLD-UHFFFAOYSA-N acetyl(dimethyl)azanium;chloride Chemical compound Cl.CN(C)C(C)=O XMMFBEWONDCTLD-UHFFFAOYSA-N 0.000 claims 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims 2
- 238000007865 diluting Methods 0.000 claims 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 2
- 238000000605 extraction Methods 0.000 claims 2
- 239000012266 salt solution Substances 0.000 claims 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 2
- IPHVGAPABXWWLO-UHFFFAOYSA-N 2,4,6-triiodobenzene-1,3-dicarboxylic acid Chemical class OC(=O)C1=C(I)C=C(I)C(C(O)=O)=C1I IPHVGAPABXWWLO-UHFFFAOYSA-N 0.000 claims 1
- DIJHXAHFUFBHCS-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethanol;hydrochloride Chemical compound Cl.OCCOCCO DIJHXAHFUFBHCS-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
- 238000005660 chlorination reaction Methods 0.000 claims 1
- 238000004040 coloring Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 238000010790 dilution Methods 0.000 claims 1
- 239000012895 dilution Substances 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
- 230000026045 iodination Effects 0.000 claims 1
- 238000006192 iodination reaction Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims 1
- 230000007935 neutral effect Effects 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 238000001556 precipitation Methods 0.000 claims 1
- 229940090181 propyl acetate Drugs 0.000 claims 1
- 159000000000 sodium salts Chemical class 0.000 claims 1
- 235000011149 sulphuric acid Nutrition 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 abstract 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)
Claims (17)
1 PATENTNI ZAHTEVKI l. Postopek za pripravo diklorida S-(-)-5-[[2-(acetiIoksi)-l-oksopropil]ami.no]-2,4,6-trijodo-l,3-benzendikarboksilne kisline s formulo (I)
označen s tem, da obsega reakcijo med kloridom S-(-)-[2-(acetiloksi)]propionske kisline in dikloridom S-amino^^^-trijodo-l^-benzendikarboksilne kisline, v aprotičnem dipolamem topilu in v prisotnosti halogenovodikove kisline.
2. Postopek po zahtevku l, označen s tem, da dodajamo halogenovodikovo kislino kot plin k raztopini diklorida 5-amino-2,4,6-trijodo-l,3'benzendikarboksilne kisline pred dodatkom klorida S-(-)-[2-(acetiloksi)]propionske kisline.
3. Postopek po zahtevku l, označen s tem, da kot halogenovodikovo kislino dodamo klorovodikovo kislino.
4. Postopek po zahtevku 3, označen s tem, da navedeni plinasti HCl dodamo v molskem razmerju 0, l do 3. z.
5. Postopek po zahtevku 1, označen s tem, da aprotično organsko topilo izberemo iz skupine, ki obstaja iz N,N-dimetilacetamida, Ν,Ν-dimetilformamida in N-metil-2-pirolidinona, prednostno iz N,N-dimetilacetamida.
6. Postopek po zahtevku 1, označen s tem, da HC1 dodamo kot hidroklorid dimetilacetamida.
7. Postopek po zahtevku 6, označen s tem, da dodamo navedeni hidroklorid dimetilacetamida v molskem razmeiju 0,1 do 3.
8. Postopek po zahtevku 1, označen s tem, da je reakcijska temperatura v območju med 0 in 40 °C.
9. Postopek za čiščenje in izolacijo diklorida S-(-)-5-[[2-(acetiloksi)-l-oksopropil]amino]- 2.4.6- trijodo-l,3-benzendikarboksilne kisline, po zahtevku 1, označen s tem, da obsega naslednje stopnje: • razredčenje reakcijske zmesi z eno izmed spojin izbranih izmed estrov ocetne kisline z linearnimi ali razvejenimi (C3-C5) alkoholi ali mono-, di- ali polikloro (C1-C4) alkani, v razmerju med razredčilnim topilom in aprotičnim dipolamim topilom prisotnih v reakcijski zmesi med 0,3 : 1 do 2,5 : 1 mas/mas; • ekstrakcijo z vodo v razmerju voda proti razredčilnemu topilu v območju od 0,5 do 4 mas/mas; • obarjanje produkta z vodo.
10. Postopek za čiščenje in izolacijo diklorida S-(-)-5-[[2-(acetiloksi)-l-oksopropil]amino]- 2.4.6- trijodo-l,3-benzendikarboksilne kisline, po zahtevku 9, označen s tem, da izberemo topila izmed propil acetata, n-butil acetata in metil kloroforma. 3
11. Postopek za čiščenje in izolacijo diklorida S-(-)-'5-[[2-(acetiloksi)-l-oksopropil]amino]- 2,4,6-trijodo-l,3-benzendikarboksilne kisline, po zahtevku 9, označen s tem, da izvedemo ekstrakcijo z vodo v kontinuimem ekstraktorju, napajanim z istim topilom, kot je uporabljeno za razredčenje ter z vodo na konceh, in z razredčeno zmesjo na vmesni plošči, produkt pa izoliromo s koncentriranjem faze topila.
12. Postopek za čiščenje in izolacijo diklorida S-(-)-5-[[2-(acetiloksi)-l-oksopropil]amino]- 2.4.6- trijodo-l,3-benzendikarboksilne kisline, po zahtevku 1, označen s tem, da obsega naslednje stopnje: • razredčenje reakcijske zmesi s (C3-C5) alkoholom, linearnim ali razvejenim, v razmerju med razredčilnim topilom in aprotičnim dipolamim topilom prisotnih v reakcijski zmesi med 0 in 1,5 mas/mas; • obaijanje produkta z vodo.
13. Postopek za čiščenje in izolacijo diklorida S-(-)-5-[[2-(acetiloksi)-l-oksopropil]amino]- 2.4.6- trijodo-l ,3-benzendikarboksilne kisline, po zahtevku 1, označen s tem, da obsega naslednje stopnje: • dodatek reakcijske zmesi k vodno-alkoholni raztopini, ki vsebuje (C3-C5) alkohol, linearen ali razvejen, v razmerju med razredčilnim topilom in aprotičnim dipolamim topilom prisotnih v reakcijski zmesi med 0 in 1,5 mas/mas.
14. Postopek za čiščenje in izolacijo diklorida S-(-)-5-[[2-(acetiloksi)-l-oksopropil]amino]- 2.4.6- trijodo-1,3-benzendikarboksilne kisline, po zahtevku 12, označen s tem, da izberemo alkohol iz skupine, ki obstaja iz izopropanola, terc-butanola in sek-butanola.
15. Postopek za čiščenje in izolacijo diklorida S-(-)-5-[[2-(acetiloksi)-l-oksopropil]aminol- 2.4.6- trijodo-l,3-benzendikarboksilne kisline, po zahtevku 13, označen s tem, da je množina alkohola v razmerju razredčilnega topila proti aprotičnemu dipolamemu topilu med 0,3 in 0,6 mas./mas. k
16. Postopek za čiščenje in izolacijo diklorida S-(-)-5-[[2-(acetiloksi)-l-oksopropil]amino]- 2,4,6-trijodo-l,3-benzendikarboksilne kisline, po zahtevku 9, označen s tem, da je aprotično dipolarno topilo prisotno v reakcijski zmesi Ν,Ν’-dimetilacetamid.
17. Postopek za pripravo diklorida S-(-)-5-[[2-(acetiloksi)-l-oksopropil]amino]-2,4,6-trijodo-1,3-benzendikarboksilne kisline, označen s tem, da obsega naslednje stopnje: a) katalitsko hidrogeniranje 5-nitro-l,3-benzendikarboksilne kisline v nevtralnem ali bazičnem mediju, ki daje vodno raztopino natrijeve soli 5-amino-l ,3-benzendikarboksilne kisline; b) direktno jodiranje raztopine natrijeve soli 5-amino-l,3-benzendikarboksilne kisline, ki izhaja iz stopnje a), brez nadaljnjega čiščenja z raztopino IC1 v HC1, pri čemer raztopini natrijeve soli 5-amino-l ,3-benzendikarboksilne kisline predhodno dodamo HC1 in H2SO4, da dobimo 5-amino-2,4,6-trijodo-l,3-benzendikarboksilno kislino; c) kloriranje diklorida 5-amino-2,4,6-trijodo-l,3-benzendikarboksilne kisline v heterogeni fazi med 5-amino-2,4,6-trijodo-l,3-benzendikarboksilno kislino in tionil kloridom, v topilu izbranem izmed (C7-C16) linearnih ali razvejenih ogljikovodikov, (CvCa) aromatskih ogljikovodikov, 1,1,1-trikloroetana, n-butil acetata, dyglyme (dietilenglikolcjimetileter) in v prisotnosti katalitske množine terciarnega amina, da dobimo diklorid 5-amino-2,4,6-trijodo-l,3-benzendikarboksilne kisline; d) reakcije med kloridom S-(-)-[2-(acetiloksi)]propionske kisline in dikloridom 5-amino-2,4,6-trijodo-l,3-benzendikarboksilne kisline, v aprotičnem dipolamem topilu in v prisotnosti halogenovodikove kisline. Za:
/
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 |
| IT95RM000548 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 (2)
| Publication Number | Publication Date |
|---|---|
| SI9620010A SI9620010A (en) | 1997-06-30 |
| SI9620010B true SI9620010B (sl) | 1998-08-31 |
Family
ID=26331280
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SI9620010A SI9620010B (sl) | 1995-05-23 | 1996-05-17 | Postopek za pripravo diklorida dikarboksilne kisline |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US5672735A (sl) |
| EP (1) | EP0773925B1 (sl) |
| JP (2) | JP4012567B2 (sl) |
| KR (1) | KR100269080B1 (sl) |
| CN (1) | CN1068582C (sl) |
| AT (1) | ATE189674T1 (sl) |
| AU (1) | AU698623B2 (sl) |
| BR (1) | BR9606394A (sl) |
| CA (1) | CA2195634C (sl) |
| CZ (1) | CZ290363B6 (sl) |
| DE (2) | DE69606601T2 (sl) |
| ES (1) | ES2103253T3 (sl) |
| GR (1) | GR970300028T1 (sl) |
| HU (1) | HU216537B (sl) |
| IL (1) | IL118358A (sl) |
| NO (1) | NO313697B1 (sl) |
| PL (1) | PL187308B1 (sl) |
| PT (1) | PT773925E (sl) |
| SI (1) | SI9620010B (sl) |
| SK (1) | SK8897A3 (sl) |
| WO (1) | WO1996037460A1 (sl) |
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 (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 |
| PT105770B (pt) * | 2011-06-24 | 2013-07-08 | Hovione Farmaciencia S A | Novo intermediário e seu uso na preparação de agente de contrate triiodado |
| 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 |
| HUE049284T2 (hu) | 2014-06-10 | 2020-09-28 | Bracco Imaging Spa | Eljárás (S)-2-acetiloxipropionsav és származékai elõállítására |
| 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 (sl) * | 1974-12-13 | 1978-12-29 | Savac Ag | |
| CH626873A5 (sl) * | 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 CZ CZ1997186A patent/CZ290363B6/cs not_active IP Right Cessation
- 1996-05-17 BR BR9606394A patent/BR9606394A/pt not_active Application Discontinuation
- 1996-05-17 PL PL96318284A patent/PL187308B1/pl unknown
- 1996-05-17 DE DE69606601T patent/DE69606601T2/de not_active Expired - Lifetime
- 1996-05-17 AT AT96919778T patent/ATE189674T1/de not_active IP Right Cessation
- 1996-05-17 CA CA002195634A patent/CA2195634C/en not_active Expired - Lifetime
- 1996-05-17 DE DE0773925T patent/DE773925T1/de active Pending
- 1996-05-17 CN CN96190525A patent/CN1068582C/zh not_active Expired - Lifetime
- 1996-05-17 ES ES96919778T patent/ES2103253T3/es not_active Expired - Lifetime
- 1996-05-17 WO PCT/EP1996/002104 patent/WO1996037460A1/en active IP Right Grant
- 1996-05-17 HU HU9700190A patent/HU216537B/hu unknown
- 1996-05-17 KR KR1019970700403A patent/KR100269080B1/ko not_active IP Right Cessation
- 1996-05-17 PT PT96919778T patent/PT773925E/pt unknown
- 1996-05-17 SK SK88-97A patent/SK8897A3/sk unknown
- 1996-05-17 AU AU58188/96A patent/AU698623B2/en not_active Expired
- 1996-05-17 EP EP96919778A patent/EP0773925B1/en not_active Expired - Lifetime
- 1996-05-17 JP JP53534696A patent/JP4012567B2/ja not_active Expired - Lifetime
- 1996-05-17 SI SI9620010A patent/SI9620010B/sl 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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