KR20060111536A - 생물학적 활성 메틸렌 블루 유도체(2)의 개발 - Google Patents
생물학적 활성 메틸렌 블루 유도체(2)의 개발 Download PDFInfo
- Publication number
- KR20060111536A KR20060111536A KR1020067010376A KR20067010376A KR20060111536A KR 20060111536 A KR20060111536 A KR 20060111536A KR 1020067010376 A KR1020067010376 A KR 1020067010376A KR 20067010376 A KR20067010376 A KR 20067010376A KR 20060111536 A KR20060111536 A KR 20060111536A
- Authority
- KR
- South Korea
- Prior art keywords
- phenothiazine
- ium
- compound
- formula
- alkyl
- 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.)
- Withdrawn
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- XYTHRJRWMIRVMF-UHFFFAOYSA-N [7-(dipentylamino)phenothiazin-3-ylidene]-dipropylazanium Chemical compound C1=CC(N(CCC)CCC)=CC2=[S+]C3=CC(N(CCCCC)CCCCC)=CC=C3N=C21 XYTHRJRWMIRVMF-UHFFFAOYSA-N 0.000 claims description 6
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/5415—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with carbocyclic ring systems, e.g. phenothiazine, chlorpromazine, piroxicam
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0327672.2 | 2003-11-28 | ||
| GBGB0327672.2A GB0327672D0 (en) | 2003-11-28 | 2003-11-28 | Developments in biologically active methylene blue derivatives (phenothiazines) |
| GB0329809A GB0329809D0 (en) | 2003-12-23 | 2003-12-23 | Developments in biologically active methylene blue derivatives (2) (phenothiazines) |
| GB0329809.8 | 2003-12-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20060111536A true KR20060111536A (ko) | 2006-10-27 |
Family
ID=34655223
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020067010376A Withdrawn KR20060111536A (ko) | 2003-11-28 | 2004-11-22 | 생물학적 활성 메틸렌 블루 유도체(2)의 개발 |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP1687286A1 (https=) |
| JP (1) | JP2007512297A (https=) |
| KR (1) | KR20060111536A (https=) |
| AU (1) | AU2004295148A1 (https=) |
| BR (1) | BRPI0416928A (https=) |
| CA (1) | CA2547556A1 (https=) |
| WO (1) | WO2005054217A1 (https=) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US7176308B2 (en) * | 2002-06-17 | 2007-02-13 | Verification Technologies, Inc. | Processes for preparing novel methylene blue derivative |
| SI2322517T1 (sl) | 2004-09-23 | 2019-06-28 | Wista Laboratories Ltd. | Postopki za kemijsko sintezo in čiščenje diaminofenotiazinijevih spojin, vključno metiltioninijevega klorida (MTC) |
| CN101084204B (zh) * | 2004-09-23 | 2012-12-05 | 卫思道制药有限公司 | 包括亚甲蓝(mtc)在内的二氨基吩噻嗪鎓化合物的化学合成和纯化方法 |
| WO2007110630A1 (en) * | 2006-03-29 | 2007-10-04 | Wista Laboratories Ltd. | Thioninium compounds and their use |
| SI2004155T1 (en) | 2006-03-29 | 2018-05-31 | Wista Laboratories Ltd. | Inhibitors of protein aggregation |
| ES2349322T7 (es) | 2006-03-29 | 2019-10-17 | Wista Lab Ltd | Sales de 3,7-diamino-10H-fenotiazina y su utilización |
| MY148145A (en) | 2006-07-11 | 2013-03-15 | Wista Lab Ltd | Methods of synthesis and/or purification of diaminophenothiazinium compounds |
| FR2903696B1 (fr) | 2006-07-12 | 2011-02-11 | Provence Technologies | Procede de purification de composes diaminophenothiazium |
| US8227459B2 (en) * | 2007-04-03 | 2012-07-24 | Prosetta Antiviral Inc. | Diamino-phenothiazinyl derivatives as antiviral treatments |
| FR2920775B1 (fr) | 2007-09-07 | 2009-11-06 | Pharma Hydro Dev P H D Soc Par | Nouveaux composes diaminophenothiazine, leur procede de preparation et leurs utilisations. |
| GB2453564A (en) * | 2007-10-11 | 2009-04-15 | Liverpool John Moores University | Ring-fused derivatives of 3,7-diamino- phenothiazinium & phenoselenazinium salts for use as antimicrobial agents |
| JP5868955B2 (ja) * | 2010-04-30 | 2016-02-24 | プロセッタ アンチバイラル インコーポレイテッド | 抗ウイルス化合物 |
| WO2012085250A1 (en) * | 2010-12-22 | 2012-06-28 | Ortner Cleanroom Engineering Gmbh | Clean room device with movable electromagnetic radiation source |
| EP2654806B1 (en) * | 2010-12-22 | 2019-05-22 | Ortner Cleanroom Engineering GmbH | Photodynamic control of microbial growth on surfaces |
| JP5898701B2 (ja) | 2011-02-11 | 2016-04-13 | ウィスタ ラボラトリーズ リミテッド | フェノチアジンジアミニウム塩およびそれらの使用 |
| WO2012125983A1 (en) | 2011-03-17 | 2012-09-20 | Prosetta Antiviral Inc. | Antiviral treatments |
| EP2694478B1 (en) * | 2011-04-04 | 2018-08-22 | Arizona Board of Regents, a Body Corporate of the State of Arizona acting for and on behalf of Arizona State University | Methylene violet analogs as multifunctional radical quenchers for the treatment of mitochondrial dysfunction |
| EP2699241B1 (en) * | 2011-04-20 | 2016-07-27 | Prosetta Antiviral Inc. | Antiviral compounds |
| US20120301904A1 (en) | 2011-04-26 | 2012-11-29 | Prosetta Antiviral, Inc | Multiprotein assemblies |
| AU2013341383B2 (en) | 2012-11-12 | 2017-08-24 | The Roger B. And Ann K. Mcnamee Trust U/T/A/D | Systems and methods for communicating a live event to users using the internet |
| CN105612148B (zh) * | 2013-08-15 | 2018-09-14 | 益友制药私人有限公司 | 用于纯化二氨基吩噻嗪化合物的方法 |
| WO2016031875A1 (ja) | 2014-08-27 | 2016-03-03 | 富士フイルム株式会社 | 光線力学療法用組成物、殺菌方法、殺菌システムおよび殺菌システムの作動方法 |
| EP3397623A1 (en) | 2015-12-28 | 2018-11-07 | John V. Frangioni | Method of preparing diaminophenothiazinium |
| FR3063495B1 (fr) * | 2017-03-02 | 2019-04-05 | Provepharm Life Solutions | Procede de preparation de l’iodure de 3,7-bis(dimethylamino)phenothiazine-5-ylium |
| CA3072418A1 (en) * | 2017-08-08 | 2019-02-14 | Board Of Trustees Of Michigan State University | Tunable luminescent organic salts for enhanced imaging and photodynamic therapy |
| US12215234B2 (en) | 2019-09-21 | 2025-02-04 | RK Pharma Solutions LLC | Process for the purification of methylene blue |
Family Cites Families (31)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US2794786A (en) * | 1955-05-27 | 1957-06-04 | Security Trust Company | Thionin dye-ion exchange resin indicator compounds |
| US3579339A (en) * | 1967-05-23 | 1971-05-18 | Du Pont | Photopolymerizable dispersions and elements containing nonmigratory photoreducible dyes |
| US3641016A (en) * | 1968-02-16 | 1972-02-08 | Egyt Gyogyszervegyeszeti Gyar | Thionine derivatives |
| FR2196082A5 (https=) * | 1972-08-07 | 1974-03-08 | Lucien Internal | |
| US4426446A (en) * | 1981-02-03 | 1984-01-17 | Hoffmann-La Roche Inc. | Leucocyte adherence inhibition assay for detection of cancer |
| JPS638652A (ja) * | 1986-06-27 | 1988-01-14 | Ricoh Co Ltd | 静電荷像現像用トナ− |
| CS264623B1 (cs) * | 1987-06-19 | 1989-08-14 | Capek Antonin | Biocidní prostředek |
| CA2055463C (en) * | 1989-05-11 | 1997-09-30 | Raymond F. Schinazi | Antiviral therapy using thiazine and xanthene dyes |
| WO1991016911A1 (en) * | 1990-05-01 | 1991-11-14 | The American National Red Cross | Decontamination of whole blood and cellular components by phenthiazin-5-ium-dyes plus light |
| US5220009A (en) * | 1990-05-03 | 1993-06-15 | Yeda Research And Development Company Limited | Phenothiazinium salts and their use for disinfecting aqueous effluents |
| US5344928A (en) * | 1991-04-26 | 1994-09-06 | Takeda Chemical Industries, Ltd. | Phenothiazine derivatives, their production and use |
| US5527704A (en) * | 1994-12-06 | 1996-06-18 | Baxter International Inc. | Apparatus and method for inactivating viral contaminants in body fluids |
| US5830526A (en) * | 1994-12-28 | 1998-11-03 | Fibermark, Inc. | Light-activated antimicrobial and antiviral materials |
| DE19640722A1 (de) * | 1996-10-02 | 1998-04-23 | Stiftung Fuer Lasertechnologie | Verfahren und Vorrichtung zur Zell- und Gewebezerstörung durch Methylen Blau (MB+) in Verbindung mit polychromatischem Licht im roten Frequenzbereich |
| DE19640758C2 (de) * | 1996-10-02 | 1999-11-04 | Rafael Lachky | Mittel zur Behandlung von Diskusfischen |
| US6190609B1 (en) * | 1996-11-19 | 2001-02-20 | Baxter International Inc. | Methods and apparatus for inactivating contaminants in biological fluid |
| WO1999004628A1 (en) * | 1997-07-28 | 1999-02-04 | Dermatolazer Technologies Ltd. | Phototherapy based method for treating pathogens and composition for effecting same |
| US5811471A (en) * | 1997-09-15 | 1998-09-22 | Shanbrom Technologies Llc | Disinfectant plastic sponge material |
| AU3371799A (en) * | 1998-03-30 | 1999-10-18 | Fibermark, Inc. | Light-activated antimicrobial polymeric materials |
| AUPP751298A0 (en) * | 1998-12-04 | 1999-01-07 | Csl Limited | Inactivation of non-enveloped viruses |
| JP2002534483A (ja) * | 1999-01-15 | 2002-10-15 | ライト サイエンシーズ コーポレイション | 代謝性骨障害または骨転移のための治療的組成物 |
| RU2184737C2 (ru) * | 1999-02-23 | 2002-07-10 | Институт нефтехимии и катализа АН РБ и УНЦ РАН | Органические комплексы цефалоспориновых антибиотиков, обладающие антимикробными свойствами |
| WO2001049328A1 (en) * | 2000-01-05 | 2001-07-12 | The American National Red Cross | Photodynamic inactivation of pathogens in blood by phenothiazines and oxygen |
| GB0002719D0 (en) * | 2000-02-08 | 2000-03-29 | Tissuemed Ltd | Thermal ablation of tissue |
| RU2176505C2 (ru) * | 2000-02-15 | 2001-12-10 | Третьяков Василий Васильевич | Средство, обладающее противовирусной активностью, на основе соединений серебра и золота с тиазином и способ его получения |
| CA2401624C (en) * | 2000-02-26 | 2011-08-16 | Merrill A. Biel | Photodynamic cellular and acellular organism eradication utilizing a photosensitive material and surfactant |
| JP2004502704A (ja) * | 2000-06-30 | 2004-01-29 | ジラ・インク | 上皮癌の検出のためのメチレンブルー診断剤および診断方法 |
| US6881731B1 (en) * | 2000-10-23 | 2005-04-19 | Shanbrom Technologies, Llc | Enhancers for microbiological disinfection |
| US6623513B2 (en) * | 2001-01-19 | 2003-09-23 | Advanced Photodynamic Technologies, Inc. | Apparatus and method of photodynamic eradication of organisms utilizing pyrrolnitrin |
| GB0113121D0 (en) * | 2001-05-30 | 2001-07-18 | Univ Leeds | Biologically active photosensitisers |
| RU2209072C2 (ru) * | 2001-09-25 | 2003-07-27 | Орловский Евгений Владимирович | Антивирусная композиция для лечения вич-инфицированных больных с высокой вирусной нагрузкой |
-
2004
- 2004-11-22 EP EP04798628A patent/EP1687286A1/en not_active Withdrawn
- 2004-11-22 AU AU2004295148A patent/AU2004295148A1/en not_active Abandoned
- 2004-11-22 WO PCT/GB2004/004918 patent/WO2005054217A1/en not_active Ceased
- 2004-11-22 KR KR1020067010376A patent/KR20060111536A/ko not_active Withdrawn
- 2004-11-22 CA CA002547556A patent/CA2547556A1/en not_active Abandoned
- 2004-11-22 JP JP2006540597A patent/JP2007512297A/ja not_active Abandoned
- 2004-11-22 BR BRPI0416928-0A patent/BRPI0416928A/pt not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP1687286A1 (en) | 2006-08-09 |
| BRPI0416928A (pt) | 2007-01-16 |
| CA2547556A1 (en) | 2005-06-16 |
| AU2004295148A1 (en) | 2005-06-16 |
| WO2005054217A1 (en) | 2005-06-16 |
| JP2007512297A (ja) | 2007-05-17 |
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