JP2013519680A5 - - Google Patents
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- Publication number
- JP2013519680A5 JP2013519680A5 JP2012552997A JP2012552997A JP2013519680A5 JP 2013519680 A5 JP2013519680 A5 JP 2013519680A5 JP 2012552997 A JP2012552997 A JP 2012552997A JP 2012552997 A JP2012552997 A JP 2012552997A JP 2013519680 A5 JP2013519680 A5 JP 2013519680A5
- Authority
- JP
- Japan
- Prior art keywords
- hydroxy
- chromen
- trifluoromethyl
- group
- oxo
- 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.)
- Granted
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- -1 N, N-dimethylamino Chemical group 0.000 claims 30
- 150000003839 salts Chemical class 0.000 claims 11
- 150000001875 compounds Chemical class 0.000 claims 10
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 9
- 150000002431 hydrogen Chemical class 0.000 claims 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 150000003536 tetrazoles Chemical class 0.000 claims 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 2
- IKNZBNHVVQIRTO-UHFFFAOYSA-N 2h-tetrazole-5-carboxylic acid Chemical compound OC(=O)C=1N=NNN=1 IKNZBNHVVQIRTO-UHFFFAOYSA-N 0.000 claims 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- 201000003883 Cystic fibrosis Diseases 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- ZVTQYRVARPYRRE-UHFFFAOYSA-N oxadiazol-4-one Chemical compound O=C1CON=N1 ZVTQYRVARPYRRE-UHFFFAOYSA-N 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
- AQYIDERAMPMQQN-UHFFFAOYSA-N 2-(difluoromethyl)-7-hydroxy-3-[4-(2h-tetrazol-5-yl)phenyl]chromen-4-one Chemical compound C=1C(O)=CC=C(C2=O)C=1OC(C(F)F)=C2C(C=C1)=CC=C1C1=NN=NN1 AQYIDERAMPMQQN-UHFFFAOYSA-N 0.000 claims 1
- DSPLFQVWRBCFBY-UHFFFAOYSA-N 3-[2-chloro-4-(2h-tetrazol-5-yl)phenyl]-7-hydroxy-2-(trifluoromethyl)chromen-4-one Chemical compound C=1C(O)=CC=C(C2=O)C=1OC(C(F)(F)F)=C2C(C(=C1)Cl)=CC=C1C1=NN=NN1 DSPLFQVWRBCFBY-UHFFFAOYSA-N 0.000 claims 1
- SROZAXRHCDMWDN-UHFFFAOYSA-N 3-[3-chloro-4-(2h-tetrazol-5-yl)phenyl]-7-hydroxy-2-(trifluoromethyl)chromen-4-one Chemical compound C=1C(O)=CC=C(C2=O)C=1OC(C(F)(F)F)=C2C(C=C1Cl)=CC=C1C1=NN=NN1 SROZAXRHCDMWDN-UHFFFAOYSA-N 0.000 claims 1
- JTJFNTFGSXGQCE-UHFFFAOYSA-N 3-[3-chloro-4-[7-hydroxy-4-oxo-2-(trifluoromethyl)chromen-3-yl]phenyl]-2h-1,2,4-oxadiazol-5-one Chemical compound C=1C(O)=CC=C(C2=O)C=1OC(C(F)(F)F)=C2C(C(=C1)Cl)=CC=C1C1=NOC(=O)N1 JTJFNTFGSXGQCE-UHFFFAOYSA-N 0.000 claims 1
- SEOPFLCETNIRME-UHFFFAOYSA-N 3-[3-fluoro-4-[7-hydroxy-4-oxo-2-(trifluoromethyl)chromen-3-yl]phenyl]-2h-1,2,4-oxadiazol-5-one Chemical compound C=1C(O)=CC=C(C2=O)C=1OC(C(F)(F)F)=C2C(C(=C1)F)=CC=C1C1=NOC(=O)N1 SEOPFLCETNIRME-UHFFFAOYSA-N 0.000 claims 1
- RRVFSAKXCOIFRP-UHFFFAOYSA-N 3-[4-[7-hydroxy-4-oxo-2-(trifluoromethyl)chromen-3-yl]phenyl]-2h-1,2,4-oxadiazol-5-one Chemical compound C=1C(O)=CC=C(C2=O)C=1OC(C(F)(F)F)=C2C(C=C1)=CC=C1C1=NOC(=O)N1 RRVFSAKXCOIFRP-UHFFFAOYSA-N 0.000 claims 1
- HNHMUAMHKJROPF-UHFFFAOYSA-N 3-[4-[7-hydroxy-4-oxo-2-(trifluoromethyl)chromen-3-yl]phenyl]-2h-1,2,4-thiadiazol-5-one Chemical compound C=1C(O)=CC=C(C2=O)C=1OC(C(F)(F)F)=C2C(C=C1)=CC=C1C1=NSC(=O)N1 HNHMUAMHKJROPF-UHFFFAOYSA-N 0.000 claims 1
- FUHSYKWZNQTLKC-UHFFFAOYSA-N 3-fluoro-4-[7-hydroxy-4-oxo-2-(trifluoromethyl)chromen-3-yl]benzoic acid Chemical compound FC1=CC(C(=O)O)=CC=C1C1=C(C(F)(F)F)OC2=CC(O)=CC=C2C1=O FUHSYKWZNQTLKC-UHFFFAOYSA-N 0.000 claims 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- DYTYZNFCPKSNSW-UHFFFAOYSA-N 4-(7-hydroxy-2-methyl-4-oxothiochromen-3-yl)benzoic acid Chemical compound CC=1SC2=CC(O)=CC=C2C(=O)C=1C1=CC=C(C(O)=O)C=C1 DYTYZNFCPKSNSW-UHFFFAOYSA-N 0.000 claims 1
- BOJHURJUTNFAKS-UHFFFAOYSA-N 4-[7-hydroxy-4-oxo-2-(trifluoromethyl)chromen-3-yl]-3-methylbenzoic acid Chemical compound CC1=CC(C(O)=O)=CC=C1C1=C(C(F)(F)F)OC2=CC(O)=CC=C2C1=O BOJHURJUTNFAKS-UHFFFAOYSA-N 0.000 claims 1
- QUFCZPQVMSDJLQ-UHFFFAOYSA-N 4-[7-hydroxy-4-oxo-2-(trifluoromethyl)chromen-3-yl]-n-methylsulfonylbenzamide Chemical compound C1=CC(C(=O)NS(=O)(=O)C)=CC=C1C1=C(C(F)(F)F)OC2=CC(O)=CC=C2C1=O QUFCZPQVMSDJLQ-UHFFFAOYSA-N 0.000 claims 1
- LXKDWHZAQSLWQP-UHFFFAOYSA-N 4-[8-fluoro-7-hydroxy-4-oxo-2-(trifluoromethyl)chromen-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=C(C(F)(F)F)OC2=C(F)C(O)=CC=C2C1=O LXKDWHZAQSLWQP-UHFFFAOYSA-N 0.000 claims 1
- HPCCACKAELJHMO-UHFFFAOYSA-N 4-[[3-(4-carboxyphenyl)-7-hydroxy-4-oxothiochromen-2-yl]methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CC1=C(C=2C=CC(=CC=2)C(O)=O)C(=O)C2=CC=C(O)C=C2S1 HPCCACKAELJHMO-UHFFFAOYSA-N 0.000 claims 1
- QHJHGEIEGPHPHU-UHFFFAOYSA-N 5-[7-hydroxy-4-oxo-2-(trifluoromethyl)chromen-3-yl]thiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=C(C(F)(F)F)OC2=CC(O)=CC=C2C1=O QHJHGEIEGPHPHU-UHFFFAOYSA-N 0.000 claims 1
- NTGQSLDMFCZSEC-UHFFFAOYSA-N 5-[7-hydroxy-4-oxo-2-(trifluoromethyl)chromen-3-yl]thiophene-3-carboxylic acid Chemical compound OC(=O)C1=CSC(C=2C(C3=CC=C(O)C=C3OC=2C(F)(F)F)=O)=C1 NTGQSLDMFCZSEC-UHFFFAOYSA-N 0.000 claims 1
- IYLSFMCJATULBG-UHFFFAOYSA-N 7-hydroxy-2-methyl-3-[4-(2h-tetrazol-5-yl)phenyl]chromen-4-one Chemical compound CC=1OC2=CC(O)=CC=C2C(=O)C=1C(C=C1)=CC=C1C1=NN=NN1 IYLSFMCJATULBG-UHFFFAOYSA-N 0.000 claims 1
- ZXBGKUANALHIOU-UHFFFAOYSA-N 7-hydroxy-2-methyl-3-[4-(2h-tetrazol-5-yl)phenyl]thiochromen-4-one Chemical compound CC=1SC2=CC(O)=CC=C2C(=O)C=1C(C=C1)=CC=C1C1=NN=NN1 ZXBGKUANALHIOU-UHFFFAOYSA-N 0.000 claims 1
- FGJSNLPJDMQOJH-UHFFFAOYSA-N 7-hydroxy-3-[4-(2h-tetrazol-5-yl)phenyl]-2-(trifluoromethyl)chromen-4-one Chemical compound C=1C(O)=CC=C(C2=O)C=1OC(C(F)(F)F)=C2C(C=C1)=CC=C1C1=NN=NN1 FGJSNLPJDMQOJH-UHFFFAOYSA-N 0.000 claims 1
- JSURXDDJUXDRSW-UHFFFAOYSA-N 7-hydroxy-3-[4-(2h-tetrazol-5-yl)phenyl]chromen-4-one Chemical compound C=1C(O)=CC=C(C2=O)C=1OC=C2C(C=C1)=CC=C1C1=NN=NN1 JSURXDDJUXDRSW-UHFFFAOYSA-N 0.000 claims 1
- VNVIRBPUPMNXGH-KYZUINATSA-N C1([C@H]2CC[C@@H](CC2)C2=C(OC=3C(C2=O)=CC=C(C=3)O)C(F)(F)F)=NN=NN1 Chemical compound C1([C@H]2CC[C@@H](CC2)C2=C(OC=3C(C2=O)=CC=C(C=3)O)C(F)(F)F)=NN=NN1 VNVIRBPUPMNXGH-KYZUINATSA-N 0.000 claims 1
- VPJXLPFRLZWPRZ-KYZUINATSA-N C1C[C@@H](C(=O)O)CC[C@@H]1C1=C(C(F)(F)F)OC2=CC(O)=CC=C2C1=O Chemical compound C1C[C@@H](C(=O)O)CC[C@@H]1C1=C(C(F)(F)F)OC2=CC(O)=CC=C2C1=O VPJXLPFRLZWPRZ-KYZUINATSA-N 0.000 claims 1
- VPJXLPFRLZWPRZ-DTORHVGOSA-N C1C[C@@H](C(=O)O)CC[C@H]1C1=C(C(F)(F)F)OC2=CC(O)=CC=C2C1=O Chemical compound C1C[C@@H](C(=O)O)CC[C@H]1C1=C(C(F)(F)F)OC2=CC(O)=CC=C2C1=O VPJXLPFRLZWPRZ-DTORHVGOSA-N 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- QSSJZLPUHJDYKF-UHFFFAOYSA-N Cc(cc1)ccc1C(OC)=O Chemical compound Cc(cc1)ccc1C(OC)=O QSSJZLPUHJDYKF-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30395210P | 2010-02-12 | 2010-02-12 | |
| US61/303,952 | 2010-02-12 | ||
| PCT/US2011/024353 WO2011100433A1 (en) | 2010-02-12 | 2011-02-10 | Novel s-nitrosoglutathione reductase inhibitors |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015190968A Division JP2016040285A (ja) | 2010-02-12 | 2015-09-29 | 新規のｓ−ニトロソグルタチオンレダクターゼ阻害剤 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013519680A JP2013519680A (ja) | 2013-05-30 |
| JP2013519680A5 true JP2013519680A5 (enExample) | 2014-03-20 |
| JP5878484B2 JP5878484B2 (ja) | 2016-03-08 |
Family
ID=44368117
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012552997A Expired - Fee Related JP5878484B2 (ja) | 2010-02-12 | 2011-02-10 | 新規のｓ−ニトロソグルタチオンレダクターゼ阻害剤 |
| JP2015190968A Pending JP2016040285A (ja) | 2010-02-12 | 2015-09-29 | 新規のｓ−ニトロソグルタチオンレダクターゼ阻害剤 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015190968A Pending JP2016040285A (ja) | 2010-02-12 | 2015-09-29 | 新規のｓ−ニトロソグルタチオンレダクターゼ阻害剤 |
Country Status (20)
| Country | Link |
|---|---|
| US (3) | US8759548B2 (enExample) |
| EP (1) | EP2533638B1 (enExample) |
| JP (2) | JP5878484B2 (enExample) |
| KR (1) | KR20120138746A (enExample) |
| CN (1) | CN102869255B (enExample) |
| AU (1) | AU2011215833B2 (enExample) |
| BR (1) | BR112012019529A2 (enExample) |
| CA (1) | CA2787633A1 (enExample) |
| DK (1) | DK2533638T3 (enExample) |
| ES (1) | ES2565345T3 (enExample) |
| HR (1) | HRP20160450T1 (enExample) |
| HU (1) | HUE029012T2 (enExample) |
| IL (1) | IL220956A (enExample) |
| PL (1) | PL2533638T3 (enExample) |
| RS (1) | RS54618B1 (enExample) |
| RU (1) | RU2585763C2 (enExample) |
| SI (1) | SI2533638T1 (enExample) |
| SM (1) | SMT201600135B (enExample) |
| WO (1) | WO2011100433A1 (enExample) |
| ZA (1) | ZA201205374B (enExample) |
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| EP2533637B1 (en) | 2010-02-12 | 2014-03-26 | N30 Pharmaceuticals, Inc. | Chromone inhibitors of s-nitrosoglutathione reductase |
| HUE029012T2 (en) | 2010-02-12 | 2017-02-28 | Nivalis Therapeutics Inc | New S-nitrosoglutathion reductase inhibitors |
| DK2624695T3 (en) | 2010-10-08 | 2016-01-04 | Nivalis Therapeutics Inc | NOVEL SUBSTITUTED quinoline-RELATIONS AS S-NITROSOGLUTATHIONREDUKTASEINHIBITORER |
| AU2011343518B2 (en) | 2010-12-16 | 2016-11-10 | Nivalis Therapeutics, Inc. | Novel substituted bicyclic aromatic compounds as S-nitrosoglutathione reductase inhibitors |
| WO2012170371A1 (en) * | 2011-06-10 | 2012-12-13 | N30 Pharmaceuticals, Llc | Compounds as s-nitrosoglutathione reductase inhibitors |
| US9630929B2 (en) | 2011-10-31 | 2017-04-25 | Xenon Pharmaceuticals Inc. | Benzenesulfonamide compounds and their use as therapeutic agents |
| JP6014155B2 (ja) | 2011-10-31 | 2016-10-25 | ゼノン・ファーマシューティカルズ・インコーポレイテッドＸｅｎｏｎ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃ． | ビアリールエーテルスルホンアミドおよび治療剤としてのそれらの使用 |
| SG11201408284VA (en) * | 2012-05-22 | 2015-02-27 | Xenon Pharmaceuticals Inc | N-substituted benzamides and their use in the treatment of pain |
| US10071957B2 (en) | 2012-07-06 | 2018-09-11 | Genentech, Inc. | N-substituted benzamides and methods of use thereof |
| US9550775B2 (en) | 2013-03-14 | 2017-01-24 | Genentech, Inc. | Substituted triazolopyridines and methods of use thereof |
| MX2015010775A (es) | 2013-03-15 | 2016-04-25 | Genentech Inc | Benzoxazoles sustituidos y metodos para usarlos. |
| CR20160296A (es) | 2013-11-27 | 2016-09-20 | Genentech Inc | Benzamidas sustituidas y métodos para usarlas |
| CN106715418A (zh) | 2014-07-07 | 2017-05-24 | 基因泰克公司 | 治疗化合物及其使用方法 |
| JP2018520107A (ja) | 2015-05-22 | 2018-07-26 | ジェネンテック， インコーポレイテッド | 置換ベンズアミド及びその使用方法 |
| EP3341353A1 (en) | 2015-08-27 | 2018-07-04 | Genentech, Inc. | Therapeutic compounds and methods of use thereof |
| WO2017044766A1 (en) | 2015-09-10 | 2017-03-16 | Nivalis Therapeutics, Inc. | Solid forms of an s-nitrosoglutathione reductase inhibitor |
| CN108290881B (zh) | 2015-09-28 | 2021-12-07 | 健泰科生物技术公司 | 治疗性化合物和其使用方法 |
| US10899732B2 (en) | 2015-11-25 | 2021-01-26 | Genentech, Inc. | Substituted benzamides useful as sodium channel blockers |
| EP3854782A1 (en) | 2016-03-30 | 2021-07-28 | Genentech, Inc. | Substituted benzamides and methods of use thereof |
| AU2017347549A1 (en) | 2016-10-17 | 2019-05-02 | Genentech, Inc. | Therapeutic compounds and methods of use thereof |
| JP2020511511A (ja) | 2017-03-24 | 2020-04-16 | ジェネンテック， インコーポレイテッド | ナトリウムチャネル阻害剤としての４−ピペリジン−ｎ−（ピリミジン−４−イル）クロマン−７−スルホンアミド誘導体 |
| WO2018177993A1 (de) | 2017-03-31 | 2018-10-04 | Bayer Cropscience Aktiengesellschaft | Pyrazole zur bekämpfung von arthropoden |
| AR114263A1 (es) | 2018-02-26 | 2020-08-12 | Genentech Inc | Compuestos terapéuticos y métodos para utilizarlos |
| WO2019191702A1 (en) | 2018-03-30 | 2019-10-03 | F. Hoffmann-La Roche Ag | Substituted hydro-pyrido-azines as sodium channel inhibitors |
| TW202003490A (zh) | 2018-05-22 | 2020-01-16 | 瑞士商赫孚孟拉羅股份公司 | 治療性化合物及其使用方法 |
| US20210052842A1 (en) * | 2019-08-23 | 2021-02-25 | NOTA Laboratories, LLC | Nitric oxide generating systems for nasal inhalation |
| CN117088862B (zh) * | 2023-08-22 | 2025-09-12 | 南华大学 | 一种硫代色元酮衍生物和应用 |
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| WO2009026657A1 (en) * | 2007-08-29 | 2009-03-05 | The University Of Sydney | Flavonoid ppar agonists |
| EP2581451B1 (en) * | 2007-12-13 | 2016-03-09 | Indiana University Research and Technology Corporation | Compounds for inhibiting mammalian s-nitrosoglutathione reductase |
| WO2010107476A1 (en) | 2009-03-19 | 2010-09-23 | Duke University | Inhibiting gsnor |
| EP2533637B1 (en) | 2010-02-12 | 2014-03-26 | N30 Pharmaceuticals, Inc. | Chromone inhibitors of s-nitrosoglutathione reductase |
| HUE029012T2 (en) | 2010-02-12 | 2017-02-28 | Nivalis Therapeutics Inc | New S-nitrosoglutathion reductase inhibitors |
| WO2012170371A1 (en) * | 2011-06-10 | 2012-12-13 | N30 Pharmaceuticals, Llc | Compounds as s-nitrosoglutathione reductase inhibitors |
-
2011
- 2011-02-10 HU HUE11742796A patent/HUE029012T2/en unknown
- 2011-02-10 BR BR112012019529-8A patent/BR112012019529A2/pt not_active IP Right Cessation
- 2011-02-10 KR KR1020127020738A patent/KR20120138746A/ko not_active Ceased
- 2011-02-10 CN CN201180008906.2A patent/CN102869255B/zh not_active Expired - Fee Related
- 2011-02-10 ES ES11742796.3T patent/ES2565345T3/es active Active
- 2011-02-10 US US13/521,833 patent/US8759548B2/en not_active Expired - Fee Related
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- 2011-02-10 JP JP2012552997A patent/JP5878484B2/ja not_active Expired - Fee Related
- 2011-02-10 SI SI201130784A patent/SI2533638T1/sl unknown
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- 2011-02-10 PL PL11742796T patent/PL2533638T3/pl unknown
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- 2011-02-10 EP EP11742796.3A patent/EP2533638B1/en active Active
- 2011-02-10 AU AU2011215833A patent/AU2011215833B2/en not_active Ceased
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2012
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2015
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- 2016-05-10 SM SM201600135T patent/SMT201600135B/it unknown
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