ES2702275T3 - Preparación de ioforminol, un agente de contraste de rayos X - Google Patents
Preparación de ioforminol, un agente de contraste de rayos X Download PDFInfo
- Publication number
- ES2702275T3 ES2702275T3 ES13766870T ES13766870T ES2702275T3 ES 2702275 T3 ES2702275 T3 ES 2702275T3 ES 13766870 T ES13766870 T ES 13766870T ES 13766870 T ES13766870 T ES 13766870T ES 2702275 T3 ES2702275 T3 ES 2702275T3
- Authority
- ES
- Spain
- Prior art keywords
- compound
- preparation
- ioforminol
- water
- process according
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- 239000002872 contrast media Substances 0.000 title description 24
- BFVVDRUCXCIALU-UHFFFAOYSA-N 5-[[3-[3,5-bis(2,3-dihydroxypropylcarbamoyl)-n-formyl-2,4,6-triiodoanilino]-2-hydroxypropyl]-formylamino]-1-n,3-n-bis(2,3-dihydroxypropyl)-2,4,6-triiodobenzene-1,3-dicarboxamide Chemical compound OCC(O)CNC(=O)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(N(CC(O)CN(C=O)C=2C(=C(C(=O)NCC(O)CO)C(I)=C(C(=O)NCC(O)CO)C=2I)I)C=O)=C1I BFVVDRUCXCIALU-UHFFFAOYSA-N 0.000 title description 21
- 229950004332 ioforminol Drugs 0.000 title description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 71
- 238000000034 method Methods 0.000 claims abstract description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 12
- 230000007062 hydrolysis Effects 0.000 claims abstract description 11
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 11
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims abstract description 8
- 238000011065 in-situ storage Methods 0.000 claims abstract description 7
- 125000006239 protecting group Chemical group 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical group ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 7
- 239000000243 solution Substances 0.000 claims description 7
- 239000007858 starting material Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 239000000725 suspension Substances 0.000 claims description 4
- 239000003637 basic solution Substances 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 230000001105 regulatory effect Effects 0.000 claims description 2
- 239000000203 mixture Substances 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- -1 isophthalamide compound Chemical class 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000008186 active pharmaceutical agent Substances 0.000 description 5
- 229940039231 contrast media Drugs 0.000 description 5
- 239000000539 dimer Substances 0.000 description 5
- 229960004359 iodixanol Drugs 0.000 description 5
- NBQNWMBBSKPBAY-UHFFFAOYSA-N iodixanol Chemical compound IC=1C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C(I)C=1N(C(=O)C)CC(O)CN(C(C)=O)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I NBQNWMBBSKPBAY-UHFFFAOYSA-N 0.000 description 5
- OZXJFUAPUQMTCF-UHFFFAOYSA-N [3-[[3-(2,3-diformyloxypropylcarbamoyl)-5-formamido-2,4,6-triiodobenzoyl]amino]-2-formyloxypropyl] formate Chemical compound IC1=C(NC=O)C(I)=C(C(=O)NCC(COC=O)OC=O)C(I)=C1C(=O)NCC(COC=O)OC=O OZXJFUAPUQMTCF-UHFFFAOYSA-N 0.000 description 4
- 238000006471 dimerization reaction Methods 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- NTHXOOBQLCIOLC-UHFFFAOYSA-N iohexol Chemical compound OCC(O)CN(C(=O)C)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I NTHXOOBQLCIOLC-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 229960001025 iohexol Drugs 0.000 description 2
- 229960000780 iomeprol Drugs 0.000 description 2
- NJKDOADNQSYQEV-UHFFFAOYSA-N iomeprol Chemical compound OCC(=O)N(C)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I NJKDOADNQSYQEV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000000178 monomer Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 238000010979 pH adjustment Methods 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical class CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- KIHQZLPHVZKELA-UHFFFAOYSA-N 1,3-dibromopropan-2-ol Chemical compound BrCC(O)CBr KIHQZLPHVZKELA-UHFFFAOYSA-N 0.000 description 1
- 229940051269 1,3-dichloro-2-propanol Drugs 0.000 description 1
- DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 description 1
- YIPGLACOACNFML-UHFFFAOYSA-N 1-n,3-n-bis(2,3-dihydroxypropyl)-2,4,6-triiodobenzene-1,3-dicarboxamide Chemical compound OCC(O)CNC(=O)C1=C(I)C=C(I)C(C(=O)NCC(O)CO)=C1I YIPGLACOACNFML-UHFFFAOYSA-N 0.000 description 1
- TVCINXHQUODERO-UHFFFAOYSA-N 1-n,3-n-bis(2,3-dihydroxypropyl)-5-formamido-2,4,6-triiodobenzene-1,3-dicarboxamide Chemical compound OCC(O)CNC(=O)C1=C(I)C(NC=O)=C(I)C(C(=O)NCC(O)CO)=C1I TVCINXHQUODERO-UHFFFAOYSA-N 0.000 description 1
- HUHDYASLFWQVOL-WZTVWXICSA-N 3-[[2-[[3-[acetyl(methyl)amino]-2,4,6-triiodo-5-(methylcarbamoyl)benzoyl]amino]acetyl]amino]-5-(2-hydroxyethylcarbamoyl)-2,4,6-triiodobenzoic acid;(2r,3r,4r,5s)-6-(methylamino)hexane-1,2,3,4,5-pentol Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CNC(=O)C1=C(I)C(N(C)C(C)=O)=C(I)C(C(=O)NCC(=O)NC=2C(=C(C(=O)NCCO)C(I)=C(C(O)=O)C=2I)I)=C1I HUHDYASLFWQVOL-WZTVWXICSA-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
- 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 description 1
- 206010067484 Adverse reaction Diseases 0.000 description 1
- 206010048610 Cardiotoxicity Diseases 0.000 description 1
- QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 description 1
- 206010029155 Nephropathy toxic Diseases 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000006838 adverse reaction Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- YVPYQUNUQOZFHG-UHFFFAOYSA-N amidotrizoic acid Chemical compound CC(=O)NC1=C(I)C(NC(C)=O)=C(I)C(C(O)=O)=C1I YVPYQUNUQOZFHG-UHFFFAOYSA-N 0.000 description 1
- 238000002583 angiography Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000012296 anti-solvent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 231100000259 cardiotoxicity Toxicity 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000032 diagnostic agent Substances 0.000 description 1
- 229940039227 diagnostic agent Drugs 0.000 description 1
- 229960005423 diatrizoate Drugs 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000022244 formylation Effects 0.000 description 1
- 238000006170 formylation reaction Methods 0.000 description 1
- 125000000592 heterocycloalkyl group Chemical class 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000000193 iodinated contrast media Substances 0.000 description 1
- 230000026045 iodination Effects 0.000 description 1
- 238000006192 iodination reaction Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229960004647 iopamidol Drugs 0.000 description 1
- 229940029407 ioxaglate Drugs 0.000 description 1
- TYYBFXNZMFNZJT-UHFFFAOYSA-N ioxaglic acid Chemical compound CNC(=O)C1=C(I)C(N(C)C(C)=O)=C(I)C(C(=O)NCC(=O)NC=2C(=C(C(=O)NCCO)C(I)=C(C(O)=O)C=2I)I)=C1I TYYBFXNZMFNZJT-UHFFFAOYSA-N 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 238000001728 nano-filtration Methods 0.000 description 1
- 230000007694 nephrotoxicity Effects 0.000 description 1
- 231100000417 nephrotoxicity Toxicity 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000004237 preparative chromatography Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 208000003663 ventricular fibrillation Diseases 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/46—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having carbon atoms of carboxamide groups, amino groups and at least three atoms of bromine or iodine, bound to carbon atoms of the same non-condensed six-membered aromatic ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/04—X-ray contrast preparations
- A61K49/0433—X-ray contrast preparations containing an organic halogenated X-ray contrast-enhancing agent
- A61K49/0438—Organic X-ray contrast-enhancing agent comprising an iodinated group or an iodine atom, e.g. iopamidol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO20121103 | 2012-09-27 | ||
| PCT/US2013/060092 WO2014052092A1 (en) | 2012-09-27 | 2013-09-17 | Preparation of ioforminol, an x-ray contrast agent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2702275T3 true ES2702275T3 (es) | 2019-02-28 |
Family
ID=49237721
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES13766870T Active ES2702275T3 (es) | 2012-09-27 | 2013-09-17 | Preparación de ioforminol, un agente de contraste de rayos X |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US9827334B2 (enExample) |
| EP (1) | EP2900631B1 (enExample) |
| JP (1) | JP6325547B2 (enExample) |
| KR (1) | KR20150061634A (enExample) |
| AU (1) | AU2013323982B2 (enExample) |
| BR (1) | BR112015004580A2 (enExample) |
| CA (1) | CA2881853A1 (enExample) |
| ES (1) | ES2702275T3 (enExample) |
| IN (1) | IN2015DN01186A (enExample) |
| MX (1) | MX365249B (enExample) |
| RU (1) | RU2642436C2 (enExample) |
| WO (1) | WO2014052092A1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20150061635A (ko) * | 2012-09-27 | 2015-06-04 | 지이 헬스케어 에이에스 | 아이오포르미놀의 중간체 화합물의 제조법 |
| AU2013323982B2 (en) | 2012-09-27 | 2017-11-23 | Ge Healthcare As | Preparation of Ioforminol, an X-ray contrast agent |
| CN108430362A (zh) * | 2015-12-23 | 2018-08-21 | 罗得岛州医院 | 热促进剂组合物及其使用方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL94718A (en) | 1989-07-05 | 1994-10-21 | Schering Ag | Carboxamide non-ionic contrast media and method for the preparation thereof |
| US5698739A (en) * | 1989-07-05 | 1997-12-16 | Schering Aktiengesellschaft | Carboxamide non-ionic contrast media |
| NO20043305D0 (no) | 2004-08-09 | 2004-08-09 | Amersham Health As | Preparation of lodixanol |
| WO2007055580A1 (en) * | 2005-11-10 | 2007-05-18 | Ge Healthcare As | Contrast agents and diagnostic compositions based on iodine-containing cyanuric acid derivatives |
| DK2178568T3 (da) * | 2007-07-12 | 2014-07-21 | Ge Healthcare As | Kontrastmidler |
| NZ605674A (en) | 2010-07-12 | 2014-11-28 | Ge Healthcare As | X-ray imaging at low contrast agent concentrations and/or low dose radiation |
| CN102816085B (zh) * | 2012-08-20 | 2013-08-14 | 浙江司太立制药股份有限公司 | 碘海醇杂质的制备方法 |
| AU2013323982B2 (en) | 2012-09-27 | 2017-11-23 | Ge Healthcare As | Preparation of Ioforminol, an X-ray contrast agent |
-
2013
- 2013-09-17 AU AU2013323982A patent/AU2013323982B2/en not_active Ceased
- 2013-09-17 ES ES13766870T patent/ES2702275T3/es active Active
- 2013-09-17 WO PCT/US2013/060092 patent/WO2014052092A1/en not_active Ceased
- 2013-09-17 US US14/430,148 patent/US9827334B2/en not_active Expired - Fee Related
- 2013-09-17 BR BR112015004580A patent/BR112015004580A2/pt not_active IP Right Cessation
- 2013-09-17 RU RU2015107017A patent/RU2642436C2/ru not_active IP Right Cessation
- 2013-09-17 CA CA2881853A patent/CA2881853A1/en not_active Abandoned
- 2013-09-17 MX MX2015003913A patent/MX365249B/es active IP Right Grant
- 2013-09-17 KR KR1020157007423A patent/KR20150061634A/ko not_active Ceased
- 2013-09-17 EP EP13766870.3A patent/EP2900631B1/en not_active Not-in-force
- 2013-09-17 JP JP2015534550A patent/JP6325547B2/ja active Active
-
2015
- 2015-02-13 IN IN1186DEN2015 patent/IN2015DN01186A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP2900631B1 (en) | 2018-11-14 |
| JP6325547B2 (ja) | 2018-05-16 |
| WO2014052092A1 (en) | 2014-04-03 |
| US9827334B2 (en) | 2017-11-28 |
| AU2013323982B2 (en) | 2017-11-23 |
| CA2881853A1 (en) | 2014-04-03 |
| JP2015530415A (ja) | 2015-10-15 |
| CN104661995A (zh) | 2015-05-27 |
| US20150265727A1 (en) | 2015-09-24 |
| MX365249B (es) | 2019-05-28 |
| MX2015003913A (es) | 2015-08-05 |
| BR112015004580A2 (pt) | 2017-07-04 |
| KR20150061634A (ko) | 2015-06-04 |
| EP2900631A1 (en) | 2015-08-05 |
| RU2015107017A (ru) | 2016-11-20 |
| IN2015DN01186A (enExample) | 2015-06-26 |
| RU2642436C2 (ru) | 2018-01-25 |
| AU2013323982A1 (en) | 2015-03-05 |
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