HRP20220102T1 - Postupci za kemijsku sintezu diaminofenotiazinskih spojeva uključujući metiltioninij klorid (mtc) - Google Patents
Postupci za kemijsku sintezu diaminofenotiazinskih spojeva uključujući metiltioninij klorid (mtc) Download PDFInfo
- Publication number
- HRP20220102T1 HRP20220102T1 HRP20220102TT HRP20220102T HRP20220102T1 HR P20220102 T1 HRP20220102 T1 HR P20220102T1 HR P20220102T T HRP20220102T T HR P20220102TT HR P20220102 T HRP20220102 T HR P20220102T HR P20220102 T1 HRP20220102 T1 HR P20220102T1
- Authority
- HR
- Croatia
- Prior art keywords
- optionally substituted
- disubstituted
- amino
- alkyl
- image
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 10
- 238000003786 synthesis reaction Methods 0.000 title claims 2
- 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 1
- 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 title 1
- 229960000907 methylthioninium chloride Drugs 0.000 title 1
- 238000006798 ring closing metathesis reaction Methods 0.000 claims 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 6
- 230000015572 biosynthetic process Effects 0.000 claims 5
- 239000003795 chemical substances by application Substances 0.000 claims 5
- 238000005691 oxidative coupling reaction Methods 0.000 claims 5
- 238000001914 filtration Methods 0.000 claims 4
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 230000003213 activating effect Effects 0.000 claims 3
- 150000003863 ammonium salts Chemical class 0.000 claims 3
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 claims 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 2
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical group O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims 2
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 150000003841 chloride salts Chemical class 0.000 claims 2
- 230000009635 nitrosylation Effects 0.000 claims 2
- -1 substituted-4-nitrosyl aniline Chemical class 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- TYYRFZAVEXQXSN-UHFFFAOYSA-H aluminium sulfate hexadecahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.[Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O TYYRFZAVEXQXSN-UHFFFAOYSA-H 0.000 claims 1
- 229920002678 cellulose Polymers 0.000 claims 1
- 239000001913 cellulose Substances 0.000 claims 1
- JOPOVCBBYLSVDA-UHFFFAOYSA-N chromium(6+) Chemical compound [Cr+6] JOPOVCBBYLSVDA-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 239000007800 oxidant agent Substances 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000011592 zinc chloride Substances 0.000 claims 1
- 235000005074 zinc chloride Nutrition 0.000 claims 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/30—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds
- C07C209/38—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
- C07C381/02—Thiosulfates
-
- 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
Claims (7)
1. Postupak za sintezu 3,7-bis(disupstituirani-amino)-1,9-(opcionalno supstituirani)-fenotiazin-5-ijeve soli 7, naznačen time, da postupak obuhvaća sljedeće korake, po redu:
nitrozilacija (NOS) u kojoj se N,N-disupstituirani-3-opcionalno supstituirani anilin 1, 4-nitrozilira da se dobije navedeni N,N-disupstituirani-3-opcionalno supstituirani-4-nitrozil anilin 2:
[image]
nitrozilna redukcija (NR) u kojoj se N,N-disupstituirani-3-opcionalno supstituirani-4-nitrozil anilin 2, reducira za tvorbu navedenog N,N-disupstituirani-1,4-diamino-5-opcionalno supstituiranog benzena 3:
[image]
tvorba tiosulfonske kiseline (TSAF) u kojoj se N,N-disupstituirani-1,4-diamino-5-opcionalno supstituirani benzen 3, oksidira u prisutnosti tiosulfata za dobivanje navedene tiosumporne kiseline S-{2-(amino)-3-(opcionalno supstituirani)-5-(disupstituirani-amino)-fenil}ester 4:
[image]
dok se za vrijeme ili prije tvorbe tiosumporne kiseline, dodaje aktivacijsko sredstvo,
oksidacijsko spajanje (OC) u kojemu se tiosumporna kiselina S-{2-(amino)-3-(opcionalno supstituirani)-5-(disupstituirani-amino)-fenil}ester 4, oksidacijski spaja na N,N-disupstituirani-3-opcionalno supstituirani anilin 5, koristeći oksidacijsko sredstvo koje jest ili sadrži Cr(VI), kako bi se dobio [4-{2-(tiosulfat)-4-(disupstituirani amino)-6-(opcionalno supstituirani)-fenil-imino}-3-(opcionalno supstituirani)-cikloheksa-2,5-dieniliden]-N,N-disupstituirani amonij 6:
[image]
zatvaranje prstena (RC) u kojem se navedeni [4-{2-(tiosulfat)-4-(disupstituirani amino)-6-(opcionalno supstituirani)-fenil-imino}-3-(opcionalno supstituirani)-cikloheksa-2,5-dieniliden]-N,N-disupstituirani amonij 6, podvrgava zatvaranju prstena u svrhu dobivanja 3,7-bis(disupstituirani-amino)-1,9-(opcionalno supstituirani)-fenotiazin-5-ijeve soli 7:
[image]
pri čemu:
svaki od R1 i R9 se neovisno bira od sljedećih: -H; C1-4 alkil; C2-4 alkenil; i halogenirani
C1-4 alkil;
svaki od R3NA i R3NB se neovisno bira od sljedećih: C1-4 alkil; C2-4 alkenil; i halogenirani
C1-4 alkil;
svaki od R7NA i R7NB se neovisno bira od sljedećih: C1-4 alkil; C2-4 alkenil; i halogenirani
C1-4 alkil; i
X- je halidni protuion,
uz uvjet da spoj 7 nije ZnCl2 miješana sol;
i pritom aktivacijsko sredstvo jest ili sadrži Al(III) i gdje molarni omjer od Al(III) prema
N,N-disupstituirani-1,4-diamino-5-opcionalno supstituiranom benzenu 3, iznosi od 0,05 do 1,0.
2. Postupak prema patentnom zahtjevu 1, naznačen time, da aktivacijsko sredstvo jest ili sadrži aluminijev sulfat heksadekahidrat.
3. Postupak prema patentnom zahtjevu 1 ili zahtjevu 2, naznačen time, da se korak nitrozilne redukcije (NR), korak tvorbe tiosulfonske kiseline (TSAF) i korak oksidacijskog spajanja (OC), završavaju u istoj reakcijskoj posudi.
4. Postupak prema bilo kojem od patentnih zahtjeva 1 do 3, naznačen time, da nadalje obuhvaća:
nakon navedenog koraka oksidacijskog spajanja (OC), i
nakon navedenog koraka kromatne redukcije (CR), ako postoji, i
prije navedenog zatvaranja prstena (RC),
izolaciju i pročišćavanje zwitterionskog intermedijera (IAPOZI), pri čemu se navedeni [4-{2-(tiosulfat)-4-(disupstituirani amino)-6-(opcionalno supstituirani)-fenil-imino}-3-(opcionalno supstituirani)-cikloheksa-2,5-dieniliden]-N,N-disupstituirani amonij 6, izolira i pročišćava.
5. Postupak prema bilo kojem od patentnih zahtjeva 1 do 4, naznačen time, da nadalje obuhvaća, nakon navedenog koraka zatvaranja prstena (RC), dodatni korak:
tvorbe kloridne soli (CSF), gdje navedena 3,7-bis(disupstituirani-amino)-1,9-(opcionalno supstituirani)-fenotiazin-5-ijeva sol 7, reagira s kloridom kako bi se dobila 3,7-bis(disupstituirani-amino)-1,9-(opcionalno supstituirani)-fenotiazin-5-ij kloridna sol 8:
[image]
6. Postupak prema bilo kojem od patentnih zahtjeva 1 do 5, naznačen time, da postupak obuhvaća najmanje jednu filtraciju, i time, da se filtracijsko sredstvo dodaje u reakcijsku posudu prije same filtracije.
7. Postupak prema patentnom zahtjevu 6, naznačen time, da filtracijsko sredstvo jest ili sadrži celulozu.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB1317702.7A GB201317702D0 (en) | 2013-10-07 | 2013-10-07 | Methods of chemical synthesis of diaminophenothiazinium compounds including methylthioninium chloride (MTC) |
| EP18181405.4A EP3415505B1 (en) | 2013-10-07 | 2014-10-06 | Methods of chemical synthesis of diaminophenothiazinium compounds including methylthioninium chloride (mtc) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20220102T1 true HRP20220102T1 (hr) | 2022-04-15 |
Family
ID=49630291
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20220102TT HRP20220102T1 (hr) | 2013-10-07 | 2014-10-06 | Postupci za kemijsku sintezu diaminofenotiazinskih spojeva uključujući metiltioninij klorid (mtc) |
| HRP20190374TT HRP20190374T1 (hr) | 2013-10-07 | 2019-02-27 | Postupci kemijske sinteze diaminofenotiazinskih spojeva uključujući metiltioninijev klorid (mtc) |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20190374TT HRP20190374T1 (hr) | 2013-10-07 | 2019-02-27 | Postupci kemijske sinteze diaminofenotiazinskih spojeva uključujući metiltioninijev klorid (mtc) |
Country Status (21)
| Country | Link |
|---|---|
| US (3) | US9765042B2 (hr) |
| EP (3) | EP3055291B1 (hr) |
| JP (1) | JP6505091B2 (hr) |
| CN (3) | CN110092764B (hr) |
| AU (3) | AU2014333610B2 (hr) |
| BR (2) | BR122023024801A2 (hr) |
| CA (3) | CA3131803C (hr) |
| DK (2) | DK3415505T3 (hr) |
| ES (2) | ES2713324T3 (hr) |
| GB (1) | GB201317702D0 (hr) |
| HK (1) | HK1222175A1 (hr) |
| HR (2) | HRP20220102T1 (hr) |
| MX (3) | MX2020004348A (hr) |
| MY (1) | MY177815A (hr) |
| PL (2) | PL3415505T3 (hr) |
| PT (2) | PT3415505T (hr) |
| SG (3) | SG10201907363YA (hr) |
| SI (2) | SI3415505T1 (hr) |
| TR (1) | TR201902152T4 (hr) |
| TW (2) | TWI675829B (hr) |
| WO (1) | WO2015052496A1 (hr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105130926B (zh) * | 2015-07-31 | 2018-02-13 | 江苏恒润制药有限公司 | 一种亚甲基蓝的制备方法 |
| GB201621817D0 (en) * | 2016-12-21 | 2017-02-01 | Wista Lab Ltd | Methods of chemical synthesis |
| US20220049102A1 (en) * | 2019-09-21 | 2022-02-17 | RK Pharma Solutions LLC | Process for the Purification of Methylene Blue |
| CN114989113A (zh) * | 2022-06-01 | 2022-09-02 | 山东科源制药股份有限公司 | 一种药用亚甲基蓝的精制方法 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US204796A (en) | 1878-06-11 | Improvement in the production of dye-stuffs from methyl-aniline | ||
| DE1886C (de) | 1877-12-15 | 1877-12-15 | Basf Ag | Verfahren zur darstellung blauer farbstoffe aus dimethylanilin und anderen tertiaeren aromatischen monaminen |
| US4212971A (en) * | 1979-03-08 | 1980-07-15 | American Cyanamid Company | Process for preparing methylene blue |
| CH640146A5 (de) * | 1979-05-14 | 1983-12-30 | Meyer Maschinenfabrik Ag | Filtrationsverfahren. |
| US5344928A (en) | 1991-04-26 | 1994-09-06 | Takeda Chemical Industries, Ltd. | Phenothiazine derivatives, their production and use |
| GB9506197D0 (en) | 1995-03-27 | 1995-05-17 | Hoffmann La Roche | Inhibition of tau-tau association. |
| JP2001514617A (ja) | 1997-01-21 | 2001-09-11 | ジ・アメリカン・ナショナル・レッド・クロス | 両親媒性フェノチアジン−５−イウム染料と光による全血および血液成分の細胞内および細胞外汚染除去 |
| FR2810318B1 (fr) | 2000-06-15 | 2005-09-23 | Laurent Galey | Derives de diamano-phenothiazine |
| GB0101049D0 (en) | 2001-01-15 | 2001-02-28 | Univ Aberdeen | Materials and methods relating to protein aggregation in neurodegenerative disease |
| GB2373787A (en) | 2001-03-08 | 2002-10-02 | Univ Central Lancashire | Phenothiazinium derivatives and their use to reduce pathogenic contaminants |
| WO2006032879A2 (en) | 2004-09-23 | 2006-03-30 | Wista Laboratories Ltd. | Methods of chemical synthesis and purification of diaminophenothiazinium compounds including methylthioninium chloride (mtc) |
| JP5186212B2 (ja) * | 2004-09-23 | 2013-04-17 | ウィスタ ラボラトリーズ リミテッド | メチルチオニニウム塩化物（ｍｔｃ）などのジアミノフェノチアジニウム化合物を化学合成および精製する方法 |
| CN101460222B (zh) * | 2006-03-29 | 2013-12-04 | 维斯塔实验室有限公司 | 锍化合物及其用途 |
| CN103735554B (zh) * | 2006-03-29 | 2018-03-20 | 维斯塔实验室有限公司 | 蛋白聚集抑制剂 |
| CN101511803B (zh) * | 2006-07-11 | 2012-10-31 | 维斯塔实验室有限公司 | 二氨基吩噻嗪*化合物的合成和/或纯化方法 |
| CN100436431C (zh) * | 2006-12-15 | 2008-11-26 | 贵州同济堂制药有限公司 | 药用亚甲蓝的合成方法 |
| SI2430007T1 (sl) * | 2009-05-12 | 2014-05-30 | Wista Laboratories Ltd. | Postopki kemijske sinteze diaminofenotiazinijevih spojin, ki vključujejo uporabo persulfatnih oksidantov |
-
2013
- 2013-10-07 GB GBGB1317702.7A patent/GB201317702D0/en not_active Ceased
-
2014
- 2014-10-06 SI SI201431945T patent/SI3415505T1/sl unknown
- 2014-10-06 PL PL18181405T patent/PL3415505T3/pl unknown
- 2014-10-06 MX MX2020004348A patent/MX2020004348A/es unknown
- 2014-10-06 HR HRP20220102TT patent/HRP20220102T1/hr unknown
- 2014-10-06 SG SG10201907363Y patent/SG10201907363YA/en unknown
- 2014-10-06 EP EP14789349.9A patent/EP3055291B1/en active Active
- 2014-10-06 SG SG11201602650XA patent/SG11201602650XA/en unknown
- 2014-10-06 EP EP18181405.4A patent/EP3415505B1/en active Active
- 2014-10-06 CA CA3131803A patent/CA3131803C/en active Active
- 2014-10-06 TW TW107113518A patent/TWI675829B/zh active
- 2014-10-06 ES ES14789349T patent/ES2713324T3/es active Active
- 2014-10-06 WO PCT/GB2014/053007 patent/WO2015052496A1/en active Application Filing
- 2014-10-06 SI SI201431094T patent/SI3055291T1/sl unknown
- 2014-10-06 PT PT181814054T patent/PT3415505T/pt unknown
- 2014-10-06 CN CN201910293813.7A patent/CN110092764B/zh active Active
- 2014-10-06 ES ES18181405T patent/ES2903529T3/es active Active
- 2014-10-06 CN CN202310997777.9A patent/CN117209450A/zh active Pending
- 2014-10-06 SG SG10201913293PA patent/SG10201913293PA/en unknown
- 2014-10-06 CA CA2925801A patent/CA2925801C/en active Active
- 2014-10-06 US US15/027,400 patent/US9765042B2/en active Active
- 2014-10-06 EP EP21203620.6A patent/EP4032880A3/en active Pending
- 2014-10-06 BR BR122023024801-5A patent/BR122023024801A2/pt active Search and Examination
- 2014-10-06 PT PT14789349T patent/PT3055291T/pt unknown
- 2014-10-06 TR TR2019/02152T patent/TR201902152T4/tr unknown
- 2014-10-06 DK DK18181405.4T patent/DK3415505T3/da active
- 2014-10-06 BR BR112016007618A patent/BR112016007618A2/pt active Search and Examination
- 2014-10-06 TW TW103134782A patent/TWI626237B/zh active
- 2014-10-06 JP JP2016520050A patent/JP6505091B2/ja active Active
- 2014-10-06 CN CN201480054610.8A patent/CN105683171B/zh active Active
- 2014-10-06 MY MYPI2016701234A patent/MY177815A/en unknown
- 2014-10-06 CA CA3207522A patent/CA3207522A1/en active Pending
- 2014-10-06 MX MX2016004229A patent/MX363102B/es unknown
- 2014-10-06 DK DK14789349.9T patent/DK3055291T3/en active
- 2014-10-06 PL PL14789349T patent/PL3055291T3/pl unknown
- 2014-10-06 AU AU2014333610A patent/AU2014333610B2/en active Active
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2016
- 2016-04-01 MX MX2019002620A patent/MX2019002620A/es active IP Right Grant
- 2016-09-01 HK HK16110424.7A patent/HK1222175A1/zh unknown
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2017
- 2017-07-17 AU AU2017206141A patent/AU2017206141B2/en active Active
- 2017-08-10 US US15/674,229 patent/US10047062B2/en active Active
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2018
- 2018-07-20 US US16/040,964 patent/US10421733B2/en active Active
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2019
- 2019-02-27 HR HRP20190374TT patent/HRP20190374T1/hr unknown
- 2019-05-17 AU AU2019203490A patent/AU2019203490B2/en active Active
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