DK3033331T3 - Fremgangsmåde til oprensning af diaminophenothiazinium forbindelser - Google Patents
Fremgangsmåde til oprensning af diaminophenothiazinium forbindelser Download PDFInfo
- Publication number
- DK3033331T3 DK3033331T3 DK14836833.5T DK14836833T DK3033331T3 DK 3033331 T3 DK3033331 T3 DK 3033331T3 DK 14836833 T DK14836833 T DK 14836833T DK 3033331 T3 DK3033331 T3 DK 3033331T3
- Authority
- DK
- Denmark
- Prior art keywords
- complex
- stabilized
- diaminophenothiazinium
- protonated
- methylene blue
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 67
- KPYHKEZPEDJERZ-UHFFFAOYSA-N 10h-phenothiazine-1,2-diamine Chemical class C1=CC=C2NC3=C(N)C(N)=CC=C3SC2=C1 KPYHKEZPEDJERZ-UHFFFAOYSA-N 0.000 title claims abstract description 45
- 238000004140 cleaning Methods 0.000 title 1
- 229960000907 methylthioninium chloride Drugs 0.000 claims abstract description 99
- 230000008569 process Effects 0.000 claims abstract description 52
- -1 diaminophenothiazinium compound Chemical class 0.000 claims abstract description 48
- 238000000746 purification Methods 0.000 claims abstract description 44
- 238000001953 recrystallisation Methods 0.000 claims abstract description 35
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- RBTBFTRPCNLSDE-UHFFFAOYSA-N 3,7-bis(dimethylamino)phenothiazin-5-ium Chemical compound C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 RBTBFTRPCNLSDE-UHFFFAOYSA-N 0.000 claims abstract 3
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- 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 description 56
- 239000003638 chemical reducing agent Substances 0.000 claims description 34
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- 239000011668 ascorbic acid Substances 0.000 claims description 32
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- 239000007800 oxidant agent Substances 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 17
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 16
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- 238000001914 filtration Methods 0.000 claims description 12
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- 125000003342 alkenyl group Chemical group 0.000 claims description 3
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- VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical compound SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 claims description 3
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- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 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 description 2
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- 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 description 2
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- 230000009467 reduction Effects 0.000 abstract description 12
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- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000003890 fistula Effects 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration 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
- 230000001900 immune effect Effects 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000991 leather dye Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000001165 lymph node Anatomy 0.000 description 1
- 230000001926 lymphatic effect Effects 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 210000003101 oviduct Anatomy 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 239000002824 redox indicator Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000011182 sodium carbonates Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- AODQPPLFAXTBJS-UHFFFAOYSA-M victoria blue 4R Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)N(C)C)=C(C=C1)C2=CC=CC=C2C1=[N+](C)C1=CC=CC=C1 AODQPPLFAXTBJS-UHFFFAOYSA-M 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
- C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
- C07D279/18—[b, e]-condensed with two six-membered rings
- C07D279/20—[b, e]-condensed with two six-membered rings with hydrogen atoms directly attached to the ring nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A61P33/06—Antimalarials
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/02—Antidotes
-
- 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
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Tropical Medicine & Parasitology (AREA)
- Psychiatry (AREA)
- Oncology (AREA)
- Pain & Pain Management (AREA)
- Communicable Diseases (AREA)
- Virology (AREA)
- Toxicology (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epidemiology (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Physics & Mathematics (AREA)
- Biodiversity & Conservation Biology (AREA)
- Optics & Photonics (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 (1)
| Publication Number | Publication Date |
|---|---|
| DK3033331T3 true DK3033331T3 (da) | 2018-04-30 |
Family
ID=52467850
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK14836833.5T DK3033331T3 (da) | 2013-08-15 | 2014-08-15 | Fremgangsmåde til oprensning af diaminophenothiazinium forbindelser |
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
Also Published As
| Publication number | Publication date |
|---|---|
| JP6111381B2 (ja) | 2017-04-05 |
| EP3033331B1 (en) | 2018-02-21 |
| IL243937A (en) | 2017-01-31 |
| BR112016002979A8 (pt) | 2020-02-04 |
| US9701648B2 (en) | 2017-07-11 |
| JP2016528237A (ja) | 2016-09-15 |
| CA2920505A1 (en) | 2015-02-19 |
| SG11201601003PA (en) | 2016-03-30 |
| TW201527287A (zh) | 2015-07-16 |
| TWI629267B (zh) | 2018-07-11 |
| AU2014306354A1 (en) | 2016-02-18 |
| KR20160042929A (ko) | 2016-04-20 |
| MX354492B (es) | 2018-03-07 |
| NZ630569A (en) | 2017-06-30 |
| CN105612148B (zh) | 2018-09-14 |
| EP3033331A4 (en) | 2017-01-18 |
| US20160200696A1 (en) | 2016-07-14 |
| EP3033331A1 (en) | 2016-06-22 |
| CA2920505C (en) | 2018-04-03 |
| IL243937A0 (en) | 2016-04-21 |
| CN105612148A (zh) | 2016-05-25 |
| MX2016002085A (es) | 2016-06-23 |
| KR101741235B1 (ko) | 2017-05-29 |
| WO2015021500A1 (en) | 2015-02-19 |
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