Process for producing by electrochemical methods thioethers...

Details Process for producing by electrochemical methods thioethers... Process for producing by electrochemical methods thioethers...

C - Chemistry, Metallurgy

25

B

C25B 3/04 (2006.01) C07C 319/14 (2006.01) C07C 323/58 (2006.01)

Patent

CA 2196561

Thioethers having the formula (I) R1-S-R2 are obtained, wherein R1 is optionally substituted C2-C5 alkyl, substituted phenyl, phenyl(haloalkyl C1- C4), -CH2-COOR3, R3 is H or a cation, haloformylalkyl or haloformylaryl, and R2 is -(CH2)n-CH(NHR4)-COOH, R4 is H or acetyl and n is 1 or 2, through electroreduction of a disulphide (II): R2-S-S-R2 in a basic medium to which is added a compound (III): R1-X, wherein X is halogen, in a controlled way throughout the process, while maintaining the pH between 9 and 12, in an electrochemical cell which comprises at least one cathode and one anode, a catholite and an anolite separated by a unique exchange membrane. The thioethers (I) obtained have a mucolytic activity, satisfy the specifications of the european pharmacopoeia and are appropriate to be used in pharmacy.

Le procédé permet d'obtenir des thioéthers de formule (I): R¿1?-S-R¿2? dans laquelle R¿1? représente alkyle C¿2?-C¿5? éventuellement substitué, phényle substitué, phényle(haloalkyle C¿1?-C¿4?), -CH¿2?-COOR¿3?, R¿3? représente H ou un cation, haloformylalkyle ou haloformylaryle, et R¿2? représente -(CH¿2?)¿n?-CH(NHR¿4?)-COOH, R¿4? représente H ou acétyle et n vaut 1 ou 2, au moyen d'une électroréduction d'un bisulfure (II): R¿2?-S-S-R¿2?, dans un milieu basique auquel on ajoute un composé (III): R¿1?-X dans lequel X représente halogène, cette addition se faisant de manière contrôlée tout au long du procédé et en maintenant le pH entre 9 et 12 dans une cellule électrochimique qui comprend au moins une cathode et une anode, un catholite et un anolite séparés par une membrane d'échange ionique. Les thioéthers (I) obtenus ont une activité mucolytique, sont conformes aux spécifications de la pharmacopée européenne et sont appropriés à un usage pharmaceutique.

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