JP2016528237A5 - - Google Patents
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- Publication number
- JP2016528237A5 JP2016528237A5 JP2016533750A JP2016533750A JP2016528237A5 JP 2016528237 A5 JP2016528237 A5 JP 2016528237A5 JP 2016533750 A JP2016533750 A JP 2016533750A JP 2016533750 A JP2016533750 A JP 2016533750A JP 2016528237 A5 JP2016528237 A5 JP 2016528237A5
- Authority
- JP
- Japan
- Prior art keywords
- stabilized
- acid
- diaminophenothiazinium
- protonated
- complex
- 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
Links
- 238000000034 method Methods 0.000 claims 26
- -1 diaminophenothiazinium compound Chemical class 0.000 claims 12
- 239000003638 chemical reducing agent Substances 0.000 claims 11
- CXKWCBBOMKCUKX-UHFFFAOYSA-M methylene blue Chemical compound [Cl-].C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 CXKWCBBOMKCUKX-UHFFFAOYSA-M 0.000 claims 11
- 229960000907 methylthioninium chloride Drugs 0.000 claims 11
- KPYHKEZPEDJERZ-UHFFFAOYSA-N 10h-phenothiazine-1,2-diamine Chemical compound C1=CC=C2NC3=C(N)C(N)=CC=C3SC2=C1 KPYHKEZPEDJERZ-UHFFFAOYSA-N 0.000 claims 10
- QTWZICCBKBYHDM-UHFFFAOYSA-N leucomethylene blue Chemical class C1=C(N(C)C)C=C2SC3=CC(N(C)C)=CC=C3NC2=C1 QTWZICCBKBYHDM-UHFFFAOYSA-N 0.000 claims 8
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims 6
- 239000007800 oxidant agent Substances 0.000 claims 5
- 238000000746 purification Methods 0.000 claims 5
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 claims 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 claims 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 3
- 235000010323 ascorbic acid Nutrition 0.000 claims 3
- 239000011668 ascorbic acid Substances 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical group 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 238000001953 recrystallisation Methods 0.000 claims 3
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims 2
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 239000003929 acidic solution Substances 0.000 claims 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 2
- 229960005070 ascorbic acid Drugs 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
- 229910017604 nitric acid Inorganic materials 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 230000001590 oxidative effect Effects 0.000 claims 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- DDGMDTGNGDOUPX-UHFFFAOYSA-N 7-methyliminophenothiazin-3-amine;hydrochloride Chemical compound [Cl-].C1=C(N)C=C2SC3=CC(=[NH+]C)C=CC3=NC2=C1 DDGMDTGNGDOUPX-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000000129 anionic group Chemical group 0.000 claims 1
- 229940072107 ascorbate Drugs 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- PGWTYMLATMNCCZ-UHFFFAOYSA-M azure A Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 PGWTYMLATMNCCZ-UHFFFAOYSA-M 0.000 claims 1
- KFZNPGQYVZZSNV-UHFFFAOYSA-M azure B Chemical compound [Cl-].C1=CC(N(C)C)=CC2=[S+]C3=CC(NC)=CC=C3N=C21 KFZNPGQYVZZSNV-UHFFFAOYSA-M 0.000 claims 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims 1
- 239000004327 boric acid Substances 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910001919 chlorite Inorganic materials 0.000 claims 1
- 229910052619 chlorite group Inorganic materials 0.000 claims 1
- QBWCMBCROVPCKQ-UHFFFAOYSA-N chlorous acid Chemical compound OCl=O QBWCMBCROVPCKQ-UHFFFAOYSA-N 0.000 claims 1
- 238000004587 chromatography analysis Methods 0.000 claims 1
- VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical compound SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 235000019253 formic acid Nutrition 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical class Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 238000005342 ion exchange Methods 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 claims 1
- YYGBVRCTHASBKD-UHFFFAOYSA-M methylene green Chemical compound [Cl-].C1=CC(N(C)C)=C([N+]([O-])=O)C2=[S+]C3=CC(N(C)C)=CC=C3N=C21 YYGBVRCTHASBKD-UHFFFAOYSA-M 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 229910052759 nickel Inorganic materials 0.000 claims 1
- 150000002823 nitrates Chemical class 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 239000001272 nitrous oxide Substances 0.000 claims 1
- 235000006408 oxalic acid Nutrition 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- JRKICGRDRMAZLK-UHFFFAOYSA-N peroxydisulfuric acid Chemical compound OS(=O)(=O)OOS(O)(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-N 0.000 claims 1
- 150000004968 peroxymonosulfuric acids Chemical class 0.000 claims 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 claims 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims 1
- 150000004053 quinones Chemical class 0.000 claims 1
- 150000003839 salts Chemical group 0.000 claims 1
- 229910001023 sodium amalgam Inorganic materials 0.000 claims 1
- 239000012279 sodium borohydride Substances 0.000 claims 1
- 229910000033 sodium borohydride Inorganic materials 0.000 claims 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2013903099 | 2013-08-15 | ||
| AU2013903099A AU2013903099A0 (en) | 2013-08-15 | Purification method and compounds | |
| PCT/AU2014/000807 WO2015021500A1 (en) | 2013-08-15 | 2014-08-15 | Process for the purification of diaminophenothiazinium compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016528237A JP2016528237A (ja) | 2016-09-15 |
| JP2016528237A5 true JP2016528237A5 (enExample) | 2016-10-27 |
| JP6111381B2 JP6111381B2 (ja) | 2017-04-05 |
Family
ID=52467850
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016533750A Active JP6111381B2 (ja) | 2013-08-15 | 2014-08-15 | ジアミノフェノチアジニウム化合物の精製方法 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US9701648B2 (enExample) |
| EP (1) | EP3033331B1 (enExample) |
| JP (1) | JP6111381B2 (enExample) |
| KR (1) | KR101741235B1 (enExample) |
| CN (1) | CN105612148B (enExample) |
| BR (1) | BR112016002979A8 (enExample) |
| CA (1) | CA2920505C (enExample) |
| DK (1) | DK3033331T3 (enExample) |
| IL (1) | IL243937A (enExample) |
| MX (1) | MX354492B (enExample) |
| NZ (1) | NZ630569A (enExample) |
| SG (1) | SG11201601003PA (enExample) |
| TW (1) | TWI629267B (enExample) |
| WO (1) | WO2015021500A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3375777A1 (en) | 2017-03-15 | 2018-09-19 | MIKROCHEM spol. s.r.o. | Method for preparation of 3,7-bis-(dimethylamino)-phenothiazin-5-ium chloride or bromide |
| CN112358475B (zh) * | 2020-11-30 | 2022-09-06 | 西北师范大学 | 一种苯并吡喃鎓-吩噻嗪衍生物及其制备方法和应用 |
| EP4512802A1 (en) * | 2022-04-19 | 2025-02-26 | Leadway (HK) Limited | Purification method for electron mediator |
| CN116947783A (zh) * | 2022-04-19 | 2023-10-27 | 英科隆生物技术（杭州）有限公司 | 一种电子媒介体的提纯方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2909520A (en) | 1959-10-20 | Process for making acylated | ||
| DE1886C (de) | 1877-12-15 | 1877-12-15 | Basf Ag | Verfahren zur darstellung blauer farbstoffe aus dimethylanilin und anderen tertiaeren aromatischen monaminen |
| GB1293757A (en) * | 1968-10-22 | 1972-10-25 | Paines & Byrne Ltd | A nerve stain composition |
| GB0327672D0 (en) * | 2003-11-28 | 2003-12-31 | Photopharmica Ltd | Developments in biologically active methylene blue derivatives (phenothiazines) |
| AU2004295148A1 (en) * | 2003-11-28 | 2005-06-16 | Photopharmica Limited | Developments in biologically active methylene blue derivatives (2) |
| US7790881B2 (en) * | 2004-09-23 | 2010-09-07 | Wista Laboratories Ltd. | Methods of chemical synthesis and purification of diaminophenothiazinium compounds including methylthioninium chloride (MTC) |
| PT1799662E (pt) | 2004-09-23 | 2013-07-09 | Wista Lab Ltd | Métodos de síntese química e purificação de compostos de diaminofenotiazínio incluindo cloreto de metiltionínio (mtc) |
| HUE030621T2 (en) * | 2006-07-11 | 2017-05-29 | Wista Lab Ltd | Methods for the synthesis and / or purification of diaminophenothiazinium compounds |
| FR2903696B1 (fr) * | 2006-07-12 | 2011-02-11 | Provence Technologies | Procede de purification de composes diaminophenothiazium |
| EA025033B1 (ru) * | 2011-02-11 | 2016-11-30 | Уиста Лэборэтэриз Лтд. | Диаминиевые соли фенотиазина и их применение |
-
2014
- 2014-08-15 CN CN201480055983.7A patent/CN105612148B/zh not_active Expired - Fee Related
- 2014-08-15 US US14/911,813 patent/US9701648B2/en not_active Expired - Fee Related
- 2014-08-15 TW TW103128051A patent/TWI629267B/zh not_active IP Right Cessation
- 2014-08-15 SG SG11201601003PA patent/SG11201601003PA/en unknown
- 2014-08-15 WO PCT/AU2014/000807 patent/WO2015021500A1/en not_active Ceased
- 2014-08-15 EP EP14836833.5A patent/EP3033331B1/en active Active
- 2014-08-15 NZ NZ630569A patent/NZ630569A/en not_active IP Right Cessation
- 2014-08-15 DK DK14836833.5T patent/DK3033331T3/da active
- 2014-08-15 JP JP2016533750A patent/JP6111381B2/ja active Active
- 2014-08-15 KR KR1020167005820A patent/KR101741235B1/ko not_active Expired - Fee Related
- 2014-08-15 BR BR112016002979A patent/BR112016002979A8/pt not_active Application Discontinuation
- 2014-08-15 CA CA2920505A patent/CA2920505C/en active Active
- 2014-08-15 MX MX2016002085A patent/MX354492B/es active IP Right Grant
-
2016
- 2016-02-03 IL IL243937A patent/IL243937A/en active IP Right Grant
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