Methods of chemical synthesis and purification of diaminophenothiazinium compounds including methylthioninium chloride (MTC): methods of treatment of a tauopathy condition comprising the use of thioninium compounds

Claude Michel Wischik; Janet Elizabeth Rickard; Charles Robert Harrington; David Horsley; John Mervyn David Storey; Colin Marshall; James Peter Sinclair

Methods of chemical synthesis and purification of diaminophenothiazinium compounds including methylthioninium chloride (MTC): methods of treatment of a tauopathy condition comprising the use of thioninium compounds

Claude Michel Wischik (Inventor), Janet Elizabeth Rickard (Inventor), Charles Robert Harrington (Inventor), David Horsley (Inventor), John Mervyn David Storey (Inventor), Colin Marshall (Inventor), James Peter Sinclair (Inventor)

Research output: Patent

Abstract

This invention pertains generally to the field of chemical synthesis and purification, and more specifically to methods of synthesizing and purifying certain 3,7-diaminophenothiazin-5-ium compounds (referred to herein as "diaminophenothiazinium compounds") including Methythioninium Chloride (MTC) (also known as Methylene Blue). In one embodiment, the method comprises the steps of, in order: nitrosylation (NOS); nitrosyl reduction (NR); thiosulfonic acid formation (TSAF); oxidative coupling (OC); Cr(VI) reduction (CR); isolation and purification of zwitterionic intermediate (IAPOZI); ring closure (RC); chloride salt formation (CSF); one of: sulphide treatment (ST); dimethyldithiocarbamate treatment (DT); carbonate treatment (CT); ethylenediaminetetraacetic acid treatment (EDTAT); organic extraction (OE); and recrystallisation (RX). The present invention also pertains to the resulting (high purity) compounds, compositions comprising them (e.g., tablets, capsules), and their use in methods of inactivating pathogens, and methods of medical treatment and diagnosis, etc., for example, for tauopathies, Alzheimer's disease (AD), skin cancer, melanoma, viral diseases, bacterial diseases, or protozoal diseases.

Original language	English
Patent number	US7,737,138
Publication status	Published - 15 Jun 2010

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

Fingerprint

Dive into the research topics of 'Methods of chemical synthesis and purification of diaminophenothiazinium compounds including methylthioninium chloride (MTC): methods of treatment of a tauopathy condition comprising the use of thioninium compounds'. Together they form a unique fingerprint.

Cite this

Methods of chemical synthesis and purification of diaminophenothiazinium compounds including methylthioninium chloride (MTC): methods of treatment of a tauopathy condition comprising the use of thioninium compounds . / Wischik, Claude Michel (Inventor); Rickard, Janet Elizabeth (Inventor); Harrington, Charles Robert (Inventor) et al.
Patent No.: US7,737,138. Jun 15, 2010.

Research output: Patent

Wischik, Claude Michel (Inventor) ; Rickard, Janet Elizabeth (Inventor) ; Harrington, Charles Robert (Inventor) et al. / Methods of chemical synthesis and purification of diaminophenothiazinium compounds including methylthioninium chloride (MTC) : methods of treatment of a tauopathy condition comprising the use of thioninium compounds . Patent No.: US7,737,138. Jun 15, 2010.

@misc{fd972614c49747dd81b338c06a1042f4,

title = "Methods of chemical synthesis and purification of diaminophenothiazinium compounds including methylthioninium chloride (MTC): methods of treatment of a tauopathy condition comprising the use of thioninium compounds ",

abstract = "This invention pertains generally to the field of chemical synthesis and purification, and more specifically to methods of synthesizing and purifying certain 3,7-diaminophenothiazin-5-ium compounds (referred to herein as {"}diaminophenothiazinium compounds{"}) including Methythioninium Chloride (MTC) (also known as Methylene Blue). In one embodiment, the method comprises the steps of, in order: nitrosylation (NOS); nitrosyl reduction (NR); thiosulfonic acid formation (TSAF); oxidative coupling (OC); Cr(VI) reduction (CR); isolation and purification of zwitterionic intermediate (IAPOZI); ring closure (RC); chloride salt formation (CSF); one of: sulphide treatment (ST); dimethyldithiocarbamate treatment (DT); carbonate treatment (CT); ethylenediaminetetraacetic acid treatment (EDTAT); organic extraction (OE); and recrystallisation (RX). The present invention also pertains to the resulting (high purity) compounds, compositions comprising them (e.g., tablets, capsules), and their use in methods of inactivating pathogens, and methods of medical treatment and diagnosis, etc., for example, for tauopathies, Alzheimer's disease (AD), skin cancer, melanoma, viral diseases, bacterial diseases, or protozoal diseases. ",

author = "Wischik, {Claude Michel} and Rickard, {Janet Elizabeth} and Harrington, {Charles Robert} and David Horsley and Storey, {John Mervyn David} and Colin Marshall and Sinclair, {James Peter}",

year = "2010",

month = jun,

day = "15",

language = "English",

type = "Patent",

note = "US7,737,138",

}

TY - PAT

T1 - Methods of chemical synthesis and purification of diaminophenothiazinium compounds including methylthioninium chloride (MTC)

T2 - methods of treatment of a tauopathy condition comprising the use of thioninium compounds

AU - Wischik, Claude Michel

AU - Rickard, Janet Elizabeth

AU - Harrington, Charles Robert

AU - Horsley, David

AU - Storey, John Mervyn David

AU - Marshall, Colin

AU - Sinclair, James Peter

PY - 2010/6/15

Y1 - 2010/6/15

N2 - This invention pertains generally to the field of chemical synthesis and purification, and more specifically to methods of synthesizing and purifying certain 3,7-diaminophenothiazin-5-ium compounds (referred to herein as "diaminophenothiazinium compounds") including Methythioninium Chloride (MTC) (also known as Methylene Blue). In one embodiment, the method comprises the steps of, in order: nitrosylation (NOS); nitrosyl reduction (NR); thiosulfonic acid formation (TSAF); oxidative coupling (OC); Cr(VI) reduction (CR); isolation and purification of zwitterionic intermediate (IAPOZI); ring closure (RC); chloride salt formation (CSF); one of: sulphide treatment (ST); dimethyldithiocarbamate treatment (DT); carbonate treatment (CT); ethylenediaminetetraacetic acid treatment (EDTAT); organic extraction (OE); and recrystallisation (RX). The present invention also pertains to the resulting (high purity) compounds, compositions comprising them (e.g., tablets, capsules), and their use in methods of inactivating pathogens, and methods of medical treatment and diagnosis, etc., for example, for tauopathies, Alzheimer's disease (AD), skin cancer, melanoma, viral diseases, bacterial diseases, or protozoal diseases.

AB - This invention pertains generally to the field of chemical synthesis and purification, and more specifically to methods of synthesizing and purifying certain 3,7-diaminophenothiazin-5-ium compounds (referred to herein as "diaminophenothiazinium compounds") including Methythioninium Chloride (MTC) (also known as Methylene Blue). In one embodiment, the method comprises the steps of, in order: nitrosylation (NOS); nitrosyl reduction (NR); thiosulfonic acid formation (TSAF); oxidative coupling (OC); Cr(VI) reduction (CR); isolation and purification of zwitterionic intermediate (IAPOZI); ring closure (RC); chloride salt formation (CSF); one of: sulphide treatment (ST); dimethyldithiocarbamate treatment (DT); carbonate treatment (CT); ethylenediaminetetraacetic acid treatment (EDTAT); organic extraction (OE); and recrystallisation (RX). The present invention also pertains to the resulting (high purity) compounds, compositions comprising them (e.g., tablets, capsules), and their use in methods of inactivating pathogens, and methods of medical treatment and diagnosis, etc., for example, for tauopathies, Alzheimer's disease (AD), skin cancer, melanoma, viral diseases, bacterial diseases, or protozoal diseases.

M3 - Patent

M1 - US7,737,138

ER -