JP6431842B2 - イオホルミノールの中間体化合物の調製 - Google Patents
イオホルミノールの中間体化合物の調製 Download PDFInfo
- Publication number
- JP6431842B2 JP6431842B2 JP2015534549A JP2015534549A JP6431842B2 JP 6431842 B2 JP6431842 B2 JP 6431842B2 JP 2015534549 A JP2015534549 A JP 2015534549A JP 2015534549 A JP2015534549 A JP 2015534549A JP 6431842 B2 JP6431842 B2 JP 6431842B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- mixture
- compound mixture
- ioforminol
- preparation
- 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.)
- Expired - Fee Related
Links
- 150000001875 compounds Chemical class 0.000 title claims description 62
- 238000002360 preparation method Methods 0.000 title claims description 20
- 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 claims description 19
- 229950004332 ioforminol Drugs 0.000 title claims description 17
- 239000000203 mixture Substances 0.000 claims description 48
- 238000000034 method Methods 0.000 claims description 40
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 23
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 14
- KAEGSAWWVYMWIQ-UHFFFAOYSA-N 5-amino-1-n,3-n-bis(2,3-dihydroxypropyl)-2,4,6-triiodobenzene-1,3-dicarboxamide Chemical compound NC1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I KAEGSAWWVYMWIQ-UHFFFAOYSA-N 0.000 claims description 13
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 11
- 235000019253 formic acid Nutrition 0.000 claims description 11
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 8
- 238000006170 formylation reaction Methods 0.000 claims description 8
- 239000000843 powder Substances 0.000 claims description 7
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
- 230000022244 formylation Effects 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000000524 functional group Chemical group 0.000 claims description 3
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 239000002872 contrast media Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 150000008064 anhydrides Chemical class 0.000 description 13
- -1 2,3-bis (formyloxy) propan-1-ylcarbamoyl Chemical group 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000008186 active pharmaceutical agent Substances 0.000 description 5
- 239000000539 dimer Substances 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
- 238000003786 synthesis reaction Methods 0.000 description 5
- 238000009472 formulation Methods 0.000 description 4
- 229960004359 iodixanol Drugs 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 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 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000006471 dimerization reaction Methods 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
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 229940088679 drug related substance Drugs 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000000543 intermediate Substances 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
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 239000012066 reaction slurry Substances 0.000 description 2
- RIWAPWDHHMWTRA-UHFFFAOYSA-N 1,2,3-triiodobenzene Chemical compound IC1=CC=CC(I)=C1I RIWAPWDHHMWTRA-UHFFFAOYSA-N 0.000 description 1
- KIHQZLPHVZKELA-UHFFFAOYSA-N 1,3-dibromopropan-2-ol Chemical compound BrCC(O)CBr KIHQZLPHVZKELA-UHFFFAOYSA-N 0.000 description 1
- DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-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
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-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
- 206010048610 Cardiotoxicity Diseases 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 206010029155 Nephropathy toxic Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 150000001340 alkali metals Chemical class 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
- 125000003277 amino group Chemical group 0.000 description 1
- 238000002583 angiography Methods 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 231100000259 cardiotoxicity Toxicity 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940039231 contrast media Drugs 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229960005423 diatrizoate Drugs 0.000 description 1
- 230000000447 dimerizing effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical group O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment 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
- 238000001727 in vivo Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 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
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 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 1
- 229960004647 iopamidol Drugs 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 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
- 230000003287 optical effect Effects 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000004237 preparative chromatography Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 208000003663 ventricular fibrillation Diseases 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/14—Preparation of carboxylic acid amides by formation of carboxamide groups together with reactions not involving the carboxamide groups
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/22—Separation; Purification; Stabilisation; Use of additives
- C07C231/24—Separation; Purification
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO20121102 | 2012-09-27 | ||
| NO20121102 | 2012-09-27 | ||
| PCT/US2013/060081 WO2014052091A1 (en) | 2012-09-27 | 2013-09-17 | Preparation of an intermediate compound of ioforminol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2015532280A JP2015532280A (ja) | 2015-11-09 |
| JP6431842B2 true JP6431842B2 (ja) | 2018-11-28 |
Family
ID=49274871
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015534549A Expired - Fee Related JP6431842B2 (ja) | 2012-09-27 | 2013-09-17 | イオホルミノールの中間体化合物の調製 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US9884808B2 (enExample) |
| EP (1) | EP2900632B1 (enExample) |
| JP (1) | JP6431842B2 (enExample) |
| KR (1) | KR20150061635A (enExample) |
| CN (2) | CN110003038A (enExample) |
| AU (1) | AU2013323981B2 (enExample) |
| BR (1) | BR112015004591A2 (enExample) |
| CA (1) | CA2881852A1 (enExample) |
| IN (1) | IN2015DN01185A (enExample) |
| MX (1) | MX354604B (enExample) |
| RU (1) | RU2654461C2 (enExample) |
| WO (1) | WO2014052091A1 (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2900632B1 (en) | 2012-09-27 | 2019-10-30 | Ge Healthcare As | Preparation of an intermediate compound of ioforminol |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0108638B1 (en) | 1982-11-08 | 1986-07-16 | NYEGAARD & CO. A/S | X-ray contrast agents |
| WO1997000240A1 (en) | 1995-06-16 | 1997-01-03 | Biophysica Foundation | Formyl derivatives as nonionic contrast media |
| GB9624612D0 (en) | 1996-11-26 | 1997-01-15 | Nycomed Imaging As | Process |
| GB9903109D0 (en) * | 1999-02-11 | 1999-04-07 | Nycomed Imaging As | Process |
| NO20043305D0 (no) | 2004-08-09 | 2004-08-09 | Amersham Health As | Preparation of lodixanol |
| NO20053687D0 (no) * | 2005-07-29 | 2005-07-29 | Amersham Health As | Crystallisation Process. |
| KR20100033405A (ko) * | 2007-07-12 | 2010-03-29 | 지이 헬스케어 에이에스 | 조영제 |
| US20110021822A1 (en) * | 2009-07-21 | 2011-01-27 | Ge Healthcare As | continuous deacetylation and purification process in synthesis of non-ionic x-ray contrast agents |
| JP6325547B2 (ja) * | 2012-09-27 | 2018-05-16 | ジーイー・ヘルスケア・アクスイェ・セルスカプ | Ｘ線造影剤イオホルミノールの調製 |
| EP2900632B1 (en) | 2012-09-27 | 2019-10-30 | Ge Healthcare As | Preparation of an intermediate compound of ioforminol |
-
2013
- 2013-09-17 EP EP13771008.3A patent/EP2900632B1/en active Active
- 2013-09-17 BR BR112015004591A patent/BR112015004591A2/pt not_active Application Discontinuation
- 2013-09-17 JP JP2015534549A patent/JP6431842B2/ja not_active Expired - Fee Related
- 2013-09-17 MX MX2015003912A patent/MX354604B/es active IP Right Grant
- 2013-09-17 US US14/430,155 patent/US9884808B2/en not_active Expired - Fee Related
- 2013-09-17 CA CA2881852A patent/CA2881852A1/en not_active Abandoned
- 2013-09-17 WO PCT/US2013/060081 patent/WO2014052091A1/en not_active Ceased
- 2013-09-17 KR KR1020157007427A patent/KR20150061635A/ko not_active Ceased
- 2013-09-17 AU AU2013323981A patent/AU2013323981B2/en not_active Ceased
- 2013-09-17 CN CN201910145184.3A patent/CN110003038A/zh active Pending
- 2013-09-17 RU RU2015107016A patent/RU2654461C2/ru not_active IP Right Cessation
- 2013-09-17 CN CN201380050455.8A patent/CN104661996A/zh active Pending
-
2015
- 2015-02-13 IN IN1185DEN2015 patent/IN2015DN01185A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2881852A1 (en) | 2014-04-03 |
| US20150246871A1 (en) | 2015-09-03 |
| MX2015003912A (es) | 2015-08-05 |
| IN2015DN01185A (enExample) | 2015-06-26 |
| BR112015004591A2 (pt) | 2017-07-04 |
| AU2013323981B2 (en) | 2017-09-14 |
| WO2014052091A1 (en) | 2014-04-03 |
| AU2013323981A1 (en) | 2015-03-05 |
| US9884808B2 (en) | 2018-02-06 |
| CN104661996A (zh) | 2015-05-27 |
| JP2015532280A (ja) | 2015-11-09 |
| KR20150061635A (ko) | 2015-06-04 |
| RU2015107016A (ru) | 2016-11-20 |
| CN110003038A (zh) | 2019-07-12 |
| RU2654461C2 (ru) | 2018-05-18 |
| MX354604B (es) | 2018-03-07 |
| EP2900632A1 (en) | 2015-08-05 |
| EP2900632B1 (en) | 2019-10-30 |
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