AU2008237276A1 - Phenothiazin derivatives for antiviral treatments - Google Patents
Phenothiazin derivatives for antiviral treatments Download PDFInfo
- Publication number
- AU2008237276A1 AU2008237276A1 AU2008237276A AU2008237276A AU2008237276A1 AU 2008237276 A1 AU2008237276 A1 AU 2008237276A1 AU 2008237276 A AU2008237276 A AU 2008237276A AU 2008237276 A AU2008237276 A AU 2008237276A AU 2008237276 A1 AU2008237276 A1 AU 2008237276A1
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- AU
- Australia
- Prior art keywords
- compound
- optionally substituted
- virus
- group
- 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.)
- Abandoned
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- 238000011282 treatment Methods 0.000 title description 9
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- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 208000028756 lack of coordination Diseases 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 235000021266 loss of appetite Nutrition 0.000 description 1
- 208000019017 loss of appetite Diseases 0.000 description 1
- 229960000907 methylthioninium chloride Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000010172 mouse model Methods 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 208000013465 muscle pain Diseases 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 238000002962 plaque-reduction assay Methods 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 206010037844 rash Diseases 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000000306 recurrent effect Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000003362 replicative effect Effects 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 239000012898 sample dilution Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 208000026843 stiff neck Diseases 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- JBQYATWDVHIOAR-UHFFFAOYSA-N tellanylidenegermanium Chemical compound [Te]=[Ge] JBQYATWDVHIOAR-UHFFFAOYSA-N 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
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229950003937 tolonium Drugs 0.000 description 1
- HNONEKILPDHFOL-UHFFFAOYSA-M tolonium chloride Chemical compound [Cl-].C1=C(C)C(N)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 HNONEKILPDHFOL-UHFFFAOYSA-M 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- 239000013598 vector Substances 0.000 description 1
- 210000003501 vero cell Anatomy 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Communicable Diseases (AREA)
- Veterinary Medicine (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US90992807P | 2007-04-03 | 2007-04-03 | |
| US60/909,928 | 2007-04-03 | ||
| PCT/US2008/059326 WO2008124550A1 (en) | 2007-04-03 | 2008-04-03 | Phenothiazin derivatives for antiviral treatments |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2008237276A1 true AU2008237276A1 (en) | 2008-10-16 |
Family
ID=39718949
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2008237276A Abandoned AU2008237276A1 (en) | 2007-04-03 | 2008-04-03 | Phenothiazin derivatives for antiviral treatments |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8227459B2 (enExample) |
| EP (1) | EP2137172A1 (enExample) |
| JP (1) | JP2010523591A (enExample) |
| CN (1) | CN101631780A (enExample) |
| AU (1) | AU2008237276A1 (enExample) |
| CA (1) | CA2686513C (enExample) |
| WO (1) | WO2008124550A1 (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2016202982B2 (en) * | 2009-09-24 | 2017-09-21 | TauRx Therapeutics Management Ltd | Crystalline methylthionium chloride (methylene blue) hydrates |
| BR122019022612B8 (pt) * | 2009-09-24 | 2021-07-27 | Wista Lab Ltd | forma e de mono-hidrato de cloreto de metiltionínio, seu processo de preparação, e composição farmacêutica |
| US8809317B2 (en) * | 2011-03-29 | 2014-08-19 | Prosetta Antiviral Inc. | Antiviral compounds |
| CN102958525B (zh) * | 2010-04-30 | 2017-05-24 | 普罗瑟塔抗病毒股份有限公司 | 抗病毒化合物 |
| WO2012125983A1 (en) | 2011-03-17 | 2012-09-20 | Prosetta Antiviral Inc. | Antiviral treatments |
| WO2012145567A1 (en) | 2011-04-20 | 2012-10-26 | Prosetta Antiviral Inc. | Antiviral compounds |
| US20120301904A1 (en) | 2011-04-26 | 2012-11-29 | Prosetta Antiviral, Inc | Multiprotein assemblies |
| US10153510B2 (en) | 2014-06-23 | 2018-12-11 | University Of Kentucky Research Foundation | Non-aqueous redox flow batteries including 3,7-perfluoroalkylated phenothiazine derivatives |
| US10195189B2 (en) * | 2014-12-15 | 2019-02-05 | Prosetta Antiviral, Inc. | 2-phenethenyltetrahydro isoquinolines useful as anti-HIV compounds |
| CN114605267B (zh) * | 2022-03-18 | 2024-02-23 | 北京格林凯默科技有限公司 | 2-溴-n,n-二甲基苯胺的制备方法 |
| AU2024224306A1 (en) * | 2023-02-21 | 2025-09-11 | Prosetta Biosciences, Inc. | Phenothiazinyl compounds and uses |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19640758C2 (de) * | 1996-10-02 | 1999-11-04 | Rafael Lachky | Mittel zur Behandlung von Diskusfischen |
| GB0113121D0 (en) * | 2001-05-30 | 2001-07-18 | Univ Leeds | Biologically active photosensitisers |
| BRPI0416928A (pt) * | 2003-11-28 | 2007-01-16 | Photopharmica Ltd | desenvolvimento de derivados biologicamente ativos de azul de metileno |
| US20080166304A1 (en) * | 2004-09-17 | 2008-07-10 | The General Hospital Corpoartion | Inactivation of Microorganisms With Multidrug Resistance Inhibitors and Phenothiaziniums |
| GB0420888D0 (en) * | 2004-09-20 | 2004-10-20 | Photopharmica Ltd | Compounds and uses |
| EP1799662B1 (en) * | 2004-09-23 | 2013-04-17 | Wista Laboratories Ltd. | Methods of chemical synthesis and purification of diaminophenothiazinium compounds including methylthioninium chloride (mtc) |
| DE602007008550D1 (de) * | 2006-03-29 | 2010-09-30 | Wista Lab Ltd | 3,7-diamino-10h-phenothiazinsalze und ihre verwendung |
-
2008
- 2008-04-03 CN CN200880008338A patent/CN101631780A/zh active Pending
- 2008-04-03 AU AU2008237276A patent/AU2008237276A1/en not_active Abandoned
- 2008-04-03 EP EP08745055A patent/EP2137172A1/en not_active Withdrawn
- 2008-04-03 WO PCT/US2008/059326 patent/WO2008124550A1/en not_active Ceased
- 2008-04-03 JP JP2010502312A patent/JP2010523591A/ja active Pending
- 2008-04-03 US US12/062,491 patent/US8227459B2/en active Active
- 2008-04-03 CA CA2686513A patent/CA2686513C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN101631780A (zh) | 2010-01-20 |
| US20110178071A1 (en) | 2011-07-21 |
| WO2008124550A1 (en) | 2008-10-16 |
| CA2686513A1 (en) | 2008-10-16 |
| EP2137172A1 (en) | 2009-12-30 |
| CA2686513C (en) | 2017-06-13 |
| US8227459B2 (en) | 2012-07-24 |
| JP2010523591A (ja) | 2010-07-15 |
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