C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
C07D 279/18 (2006.01) A61K 31/54 (2006.01) A61P 25/28 (2006.01) A61P 35/00 (2006.01)
Patent
CA 2579169
This invention pertains generally to the field of chemical synthesis and purification, and more specifically to methods of synthesizing and purifying certain 3,7 diamino-phenothiazin-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. Wherein: each of R1 and R9 is independently selected from:-H; C1-4 alkenyl; and halogenated C1-4akyl; each of R3NA and R3NBis independently selected from: C1-4 alkyl; C2-4alkenyl; and halogenated C4-1 alkyl; each of R7NA and R7NB is independently selected from: C1-4 alkyl; C2-4alkenyl; and halogenated C1-4 alkyl; and X is one or more anionic counter ions to achieve electrical neutrality.
L'invention concerne en règle générale le domaine de la synthèse chimique et de la purification, et plus précisément des procédés de synthèse et de purification de certains composés de 3,7 diamino-phénothiazin-5-ium (que l'on appellera "composés diaminophénothiazinium") renfermant du chlorure de méthythioninium (MTC) (connu sous le nom de bleu de méthylène). Selon une variante, le procédé comprend les étapes suivantes, dans cet ordre: nitrosylation (NOS); réduction de nitrosyle (NR); formation d'acide thiosulfonique (TSAF); couplage oxydatif (OC); réduction de Cr(VI) (CR); isolation et purification d'intermédiaire zwittérionique (IAPOZI); fermeture de chaîne (RC); formation de sel chlorure (CSF); au choix, l'une des opérations suivantes: traitement sulphure (ST); traitement diméthyldithiocarbamate (DT); traitement carbonate (CT); traitement acide éthylènediaminetétraacétique (EDTAT); extraction organique (OE); et recristallisation (RX). On décrit aussi des composés résultants (pureté élevée), des compositions qui les renferment (par exemple, comprimés, capsules), et leur utilisation dans le cadre de procédés d'inactivation de pathogènes, ou de traitement médical et de diagnostic, etc., par exemple pour les tauopathies, la maladie d'Alzheimer (AD), le cancer de la peau, le mélanome, les maladies virales, bactériennes ou protozoaires.
Marshall Colin
Sinclair James Peter
Storey John Mervyn David
Tan Han Wan
Wischik Claude Michel
Kirby Eades Gale Baker
Wista Laboratories Ltd.
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