HRP20140431T1 - Postupak za jodiranje aromatskih tvari - Google Patents
Postupak za jodiranje aromatskih tvari Download PDFInfo
- Publication number
- HRP20140431T1 HRP20140431T1 HRP20140431AT HRP20140431T HRP20140431T1 HR P20140431 T1 HRP20140431 T1 HR P20140431T1 HR P20140431A T HRP20140431A T HR P20140431AT HR P20140431 T HRP20140431 T HR P20140431T HR P20140431 T1 HRP20140431 T1 HR P20140431T1
- Authority
- HR
- Croatia
- Prior art keywords
- process according
- formula
- acid
- preparation
- iodine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 20
- 230000026045 iodination Effects 0.000 title claims 2
- 238000006192 iodination reaction Methods 0.000 title claims 2
- 150000001491 aromatic compounds Chemical class 0.000 title 1
- 239000000758 substrate Substances 0.000 claims 7
- QFWPJPIVLCBXFJ-UHFFFAOYSA-N glymidine Chemical compound N1=CC(OCCOC)=CN=C1NS(=O)(=O)C1=CC=CC=C1 QFWPJPIVLCBXFJ-UHFFFAOYSA-N 0.000 claims 6
- 239000000126 substance Substances 0.000 claims 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 4
- 229910052740 iodine Inorganic materials 0.000 claims 4
- 239000011630 iodine Substances 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 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 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 230000002378 acidificating effect Effects 0.000 claims 2
- 239000007864 aqueous solution Substances 0.000 claims 2
- 239000003125 aqueous solvent Substances 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical group O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 239000002798 polar solvent Substances 0.000 claims 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- ALHZEIINTQJLOT-UHFFFAOYSA-N (1-chloro-1-oxopropan-2-yl) acetate Chemical compound ClC(=O)C(C)OC(C)=O ALHZEIINTQJLOT-UHFFFAOYSA-N 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- KJJPLEZQSCZCKE-UHFFFAOYSA-N 2-aminopropane-1,3-diol Chemical compound OCC(N)CO KJJPLEZQSCZCKE-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
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 125000005518 carboxamido group Chemical group 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000012045 crude solution Substances 0.000 claims 1
- 150000002334 glycols Chemical class 0.000 claims 1
- ICIWUVCWSCSTAQ-UHFFFAOYSA-N iodic acid Chemical compound OI(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- 229940098779 methanesulfonic acid Drugs 0.000 claims 1
- 230000020477 pH reduction Effects 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 230000035484 reaction time Effects 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 159000000000 sodium salts Chemical class 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 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
- C07C227/16—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 not involving the amino or carboxyl groups
-
- 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
- C07C227/38—Separation; Purification; Stabilisation; Use of additives
- C07C227/40—Separation; Purification
- C07C227/42—Crystallisation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3819—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen
- C08G18/3821—Carboxylic acids; Esters thereof with monohydroxyl compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (15)
1. Postupak za pripremu 5-amino-2,4,6-trijodoizoftalne kiseline formule (II)
[image]
obuhvaća jodiranje, provedeno u polarnom otapalu i u kiselim uvjetima, 5-aminoizoftalne kiseline formule (I)
[image]
ili njene soli s molekularnim jodom i u prisustvu jodne kiseline pri čemu je molarni omjer između molekularnog joda i 5-aminoizoftalnog supstrata (I) sadržan između 1 i 1.5, molarni omjer joda prema jodnoj kiselini nalazi se u rasponu od 1 : 0.5 do 1 : 1, a omjer ekvivalenata između 5-aminoizoftalnog supstrata (I) i jodirajuće vrste, koja podrazumijeva zbroj I2 i HIO3, iznosi najmanje 1:3.
2. Postupak u skladu s patentnim zahtjevom 1 pri čemu je molarni omjer između molekularnog joda i 5-aminoizoftalnog supstrata (I) sadržan između 1 do 1.3, a molarni omjer joda prema jodnoj kiselini je sadržan između 1 : 0.5 do 1 : 0.8.
3. Postupak u skladu s patentnim zahtjevom 2 u kojem je trijodinacija 5-aminoizoftalnog supstrata jodom i jodnom kiselinom provedena koristeći molarni omjer 5-aminoizoftalnog supstrata : joda : jodne kiseline od 1 : 1.2 : 0.6.
4. Postupak u skladu s bilo kojim od patentnih zahtjeva 1 do 3 pri čemu su kiseli uvjeti postignuti u prisustvu kiseline odabrane između fosforne, metansulfonske ili sulfurne kiseline.
5. Postupak u skladu s bilo kojim od patentnih zahtjeva 1 do 4 pri čemu je polarno otapalo odabrano između vode ili vodenog otapala, nižih alkohola C1-C4 i njihovih hidroalkoholnih smjesa, dioksana, glikola i njihovih vdenih smjesa.
6. Postupak u skladu s patentnim zahtjevom 5 pri čemu je otapalo voda ili vodeno otapalo.
7. Postupak u skladu s patentnim zahtjevom 6 koji obuhvaća dodavanje molekularnog I2 i jodne kiseline u vodenu otopinu 5-aminoizoftalnog supstrata koji ima pH niži od 3.5.
8. Postupak u skladu s patentnim zahtjevom 7 pri čemu je navedena vodena otopina dobivena izravnim zakiseljavanjem sirove otopine iz industrijskog postupka koja sadrži 5-aminoizoftalni supstrat kao natrijevu sol.
9. Postupak u skladu s patentnim zahtjevima 7 ili 8 pri čemu je navedeni pH sadržan između 1 i 3.
10. Postupak u skladu s bilo kojim od patentnih zahtjeva 1 do 9 proveden na temperaturi sadržanoj između 50°C do 85°C.
11. Postupak u skladu s bilo kojim od patentnih zahtjeva 1 do 10 pri čemu je vrijeme reakcije sadržano između 2 do 10 sati.
12. Postupak za pripravu tvari formule (III)
[image]
pri čemu:
R i R' predstavljaju, istu ili međusobno različitu, grupu odabranu između karboksi (-COOH), karboksiester (-COOR1) i karboksoamido (-CONH2, -CONHR1 ili –CONR2R3), pri čemu su R1, R2 i R3, iste ili međusobno različite, ravne ili razgranate C1-C4 alkilne grupe proizvoljno supstituirane jednom ili više hidroksilnih grupa, a R4 i R5 su, isti ili međusobno različiti, vodik ili ravna ili razgranata C1-C6 alkilna grupa proizvoljno supstituirana jednim ili više hidroksil ili C1-C6 alkoksi grupa, navedeni postupak obuhvaća pripremu intermedijarne tvari formule (II) prema postupku iz bilo kojeg od patentnih zahtjeva 1-11.
13. Postupak u skladu s patentnim zahtjevom 12 za pripremu tvari formule (III) pri čemu su oboje R i R' –CONH-CH(CH2OH)2 grupe, R4 je vodik i R5 je metilna grupa.
14. Postupak u skladu s patentnim zahtjevom 12 za pripremu tvari formule (III) pri čemu su oboje R i R' –CONH-CH2-CH(OH)CH2OH, R4 je metil i R5 je vodik.
15. Postupak u skladu s patentnim zahtjevom 13 za pripravu lopamidola obuhvaća:
a) pripremu 5-amino-2,4,6-trijodoizoftalne kiseline formule (II) u skladu s postupkom iz bilo kojeg od patentnih zahtjeva 1-11; navedeni postupak nadalje obuhvaća:
b) pretvorbu tvari formule (II) u diklorid odgovarajuće kiseline, u prisustvu tionil klorida,
c) kondenziranje dobivenog diklorida s kloridom 2-[(acetiloksi)]propionske kiseline zbog dobivanja odgovarajućeg 5-karboksamido derivata, i
d) kondenziranje dobivenog derivata sa serinolom i uklanjanje proizvoljne zaštitne grupe zbog dobivanja tvari formule (III).
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP09158319A EP2243767A1 (en) | 2009-04-21 | 2009-04-21 | Process for the iodination of aromatic compounds |
| PCT/EP2010/054624 WO2010121904A1 (en) | 2009-04-21 | 2010-04-08 | Process for the iodination of aromatic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20140431T1 true HRP20140431T1 (hr) | 2014-07-18 |
Family
ID=40668303
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20140431AT HRP20140431T1 (hr) | 2009-04-21 | 2014-05-12 | Postupak za jodiranje aromatskih tvari |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US9238615B2 (hr) |
| EP (2) | EP2243767A1 (hr) |
| JP (1) | JP5469240B2 (hr) |
| KR (1) | KR101774332B1 (hr) |
| CN (1) | CN102428068B (hr) |
| AU (1) | AU2010241071B2 (hr) |
| BR (1) | BRPI1013830B1 (hr) |
| CA (1) | CA2759342C (hr) |
| DK (1) | DK2421819T3 (hr) |
| ES (1) | ES2469846T3 (hr) |
| HR (1) | HRP20140431T1 (hr) |
| IL (1) | IL215685A (hr) |
| PL (1) | PL2421819T3 (hr) |
| PT (1) | PT2421819E (hr) |
| RU (1) | RU2506254C2 (hr) |
| SI (1) | SI2421819T1 (hr) |
| WO (1) | WO2010121904A1 (hr) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2394984A1 (en) * | 2010-06-10 | 2011-12-14 | Bracco Imaging S.p.A | Process for the iodination of phenolic derivatives |
| JP6140175B2 (ja) * | 2011-10-31 | 2017-05-31 | アイマックス ダイアグノスティック イメージング ホールディング リミテッド | ３，５−二置換−２，４，６−トリヨード芳香族アミン化合物の製造のためのヨウ素化方法 |
| CN103086915A (zh) * | 2011-10-31 | 2013-05-08 | 上海海神化学生物科技有限公司 | 制备3,5-二取代-2,4,6-三碘代芳香胺类化合物的碘化方法 |
| RU2657238C2 (ru) | 2013-11-05 | 2018-06-09 | Бракко Имэджинг Спа | Способ получения йопамидола |
| CN104098484A (zh) * | 2014-07-21 | 2014-10-15 | 杭州杜易科技有限公司 | 一种碘帕醇的制备方法 |
| JP6743781B2 (ja) * | 2016-08-08 | 2020-08-19 | 信越化学工業株式会社 | レジスト材料及びパターン形成方法 |
| CN114685746A (zh) | 2016-12-02 | 2022-07-01 | 得克萨斯农业及机械体系综合大学 | 形状记忆聚合物栓塞泡沫 |
| CN110105233A (zh) * | 2018-06-01 | 2019-08-09 | 成都西岭源药业有限公司 | 一种制备5-氨基-2,4,6-三碘间苯二甲酸的方法 |
| CN110724061A (zh) * | 2019-10-21 | 2020-01-24 | 新岸诺亚（北京）催化科技有限公司 | 一种对碘苯胺及其制备方法 |
| CN111249459A (zh) * | 2020-01-19 | 2020-06-09 | 东华大学 | 一种具有ct造影功能的含碘聚苯胺光热诊疗剂及其制备 |
| CN113444007A (zh) * | 2021-07-30 | 2021-09-28 | 成都倍特药业股份有限公司 | 一种制备5-氨基-2,4,6-三碘间苯二甲酸的方法 |
Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2820814A (en) * | 1955-03-21 | 1958-01-21 | Schering Corp | Polyiodinated 5-aminoisophthalic acids, salts, and esters |
| CA935164A (en) * | 1968-12-06 | 1973-10-09 | Sumimoto Shinzaburo | Industrial process for iodinating aromatic compounds by using novel iodinating reagents |
| CH608189A5 (hr) * | 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 |
| AU618535B2 (en) | 1987-05-22 | 1992-01-02 | Bracco International B.V. | Preparation of 5-acylamino-2,4,6-triiodo-or tribromo-benzoic acid derivatives |
| 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 |
| US5075502A (en) * | 1989-12-13 | 1991-12-24 | Mallinckrodt, Inc. | Nonionic x-ray contrast agents, compositions and methods |
| SG49221A1 (en) * | 1990-03-09 | 1998-05-18 | Nycomed As | Contrast media |
| GB9020091D0 (en) | 1990-09-14 | 1990-10-24 | Nycomed As | Contrast media |
| FR2673180B1 (fr) | 1991-02-25 | 1994-03-04 | Guerbet Sa | Nouveaux composes non ioniques poly-iodes, procede de preparation, produit de contraste les contenant. |
| IT1256162B (it) | 1992-10-27 | 1995-11-29 | Zambon Spa | Processo per la preparazione di un intermedio della sintesi organica |
| IT1256248B (it) | 1992-12-24 | 1995-11-29 | Bracco Spa | Formulazioni iniettabili acquose per radiodiagnostica comprendenti miscele di composti aromatici iodurati utili come agenti opacizzanti ai raggi x |
| JPH06345705A (ja) * | 1993-06-03 | 1994-12-20 | Terumo Corp | テトラヨードベンゼン誘導体 |
| ATE189674T1 (de) | 1995-05-23 | 2000-02-15 | Fructamine Spa | Verfahren zur herstellung von dicarbonsäure- dichlorid |
| US5763650A (en) | 1995-05-23 | 1998-06-09 | Fructamine S.P.A. | Process for the preparation of a halosubstituted aromatic acid |
| US5616795A (en) | 1995-05-23 | 1997-04-01 | Fructamine S.P.A. | Process for the preparation of a dicarboxylic acid dichloride |
| EP0828705B1 (en) | 1995-05-24 | 2000-08-23 | Nycomed Imaging As | Iodination process |
| IT1277339B1 (it) | 1995-07-25 | 1997-11-10 | Bracco Spa | Processo per la produzione di agenti contrastografici iodurati |
| IT1288114B1 (it) | 1996-06-13 | 1998-09-10 | Fructamine Spa | Processo per la purificazione di un intermedio |
| IT1286522B1 (it) | 1996-12-04 | 1998-07-15 | Dibra Spa | Processo per la preparazione di derivati dell'acido 5-ammino-2,4,6- triiodo-1,3-benzenedicarbossilico |
| JPH10316639A (ja) * | 1997-05-16 | 1998-12-02 | Mitsui Chem Inc | ５−アミノ−２，４，６−トリヨードイソフタル酸の製造法 |
| GB9710725D0 (en) * | 1997-05-23 | 1997-07-16 | Nycomed Imaging As | Process |
| JPH10330336A (ja) * | 1997-06-03 | 1998-12-15 | Mitsui Chem Inc | ５−アミノ−２，４，６−トリヨードイソフタル酸の製造方法 |
| EP0992245A1 (en) * | 1998-09-16 | 2000-04-12 | Goldham Bioglan Pharma GmbH | Radio-contrast agents |
| IT1303797B1 (it) | 1998-11-27 | 2001-02-23 | Bracco Spa | Processo per la preparazione di n,n'-bis(2,3-diidrossipropil)-5-((idrossiacetil)metilammino)-2,4,6-triiodo-1,3-benzendicarbossammide. |
| WO2002000642A1 (en) * | 2000-06-26 | 2002-01-03 | The Research Foundation Of State University Of New York | Method for preparation of an intermediate dye product |
| ITMI20011706A1 (it) * | 2001-08-03 | 2003-02-03 | Bracco Imaging Spa | Agenti di contrasto radiografici ionici e non ionici, utilizzabili per l'indagine diagnostica combinata tramite raggi-x e risonanza magnetic |
| EP1777215B1 (en) | 2004-08-10 | 2010-11-03 | Mitsubishi Gas Chemical Company, Inc. | Method for producing 2-amino-5-iodobenzoic acid |
| JP2008074722A (ja) * | 2006-09-19 | 2008-04-03 | Mitsubishi Gas Chem Co Inc | ２−アミノ−５−ヨード安息香酸の製造方法 |
| EP2093206A1 (en) | 2008-02-20 | 2009-08-26 | BRACCO IMAGING S.p.A. | Process for the iodination of aromatic compounds |
-
2009
- 2009-04-21 EP EP09158319A patent/EP2243767A1/en not_active Withdrawn
-
2010
- 2010-04-08 WO PCT/EP2010/054624 patent/WO2010121904A1/en active Application Filing
- 2010-04-08 US US13/265,165 patent/US9238615B2/en active Active
- 2010-04-08 RU RU2011147046/04A patent/RU2506254C2/ru active
- 2010-04-08 BR BRPI1013830-7A patent/BRPI1013830B1/pt active IP Right Grant
- 2010-04-08 AU AU2010241071A patent/AU2010241071B2/en active Active
- 2010-04-08 CA CA2759342A patent/CA2759342C/en active Active
- 2010-04-08 JP JP2012506434A patent/JP5469240B2/ja active Active
- 2010-04-08 PT PT107181042T patent/PT2421819E/pt unknown
- 2010-04-08 CN CN201080017568.4A patent/CN102428068B/zh active Active
- 2010-04-08 ES ES10718104.2T patent/ES2469846T3/es active Active
- 2010-04-08 KR KR1020117024801A patent/KR101774332B1/ko active IP Right Grant
- 2010-04-08 DK DK10718104.2T patent/DK2421819T3/da active
- 2010-04-08 SI SI201030616T patent/SI2421819T1/sl unknown
- 2010-04-08 PL PL10718104T patent/PL2421819T3/pl unknown
- 2010-04-08 EP EP10718104.2A patent/EP2421819B1/en active Active
-
2011
- 2011-10-10 IL IL215685A patent/IL215685A/en active IP Right Grant
-
2014
- 2014-05-12 HR HRP20140431AT patent/HRP20140431T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR101774332B1 (ko) | 2017-09-04 |
| KR20120016056A (ko) | 2012-02-22 |
| AU2010241071B2 (en) | 2014-03-13 |
| SI2421819T1 (sl) | 2014-08-29 |
| CA2759342C (en) | 2016-01-05 |
| PL2421819T3 (pl) | 2014-08-29 |
| ES2469846T3 (es) | 2014-06-20 |
| RU2506254C2 (ru) | 2014-02-10 |
| RU2011147046A (ru) | 2013-05-27 |
| CN102428068A (zh) | 2012-04-25 |
| AU2010241071A1 (en) | 2011-10-20 |
| IL215685A0 (en) | 2012-01-31 |
| CA2759342A1 (en) | 2010-10-28 |
| DK2421819T3 (da) | 2014-06-10 |
| JP2012524741A (ja) | 2012-10-18 |
| PT2421819E (pt) | 2014-06-06 |
| JP5469240B2 (ja) | 2014-04-16 |
| EP2243767A1 (en) | 2010-10-27 |
| BRPI1013830B1 (pt) | 2019-03-06 |
| WO2010121904A1 (en) | 2010-10-28 |
| IL215685A (en) | 2016-04-21 |
| US20120041224A1 (en) | 2012-02-16 |
| US9238615B2 (en) | 2016-01-19 |
| CN102428068B (zh) | 2014-10-15 |
| BRPI1013830A2 (pt) | 2010-10-28 |
| EP2421819A1 (en) | 2012-02-29 |
| EP2421819B1 (en) | 2014-03-05 |
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