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1. WO1996038601 - PROCESS FOR PRODUCING BY ELECTROCHEMICAL METHODS THIOETHERS FOR PHARMACEUTICAL USE

Publication Number WO/1996/038601
Publication Date 05.12.1996
International Application No. PCT/ES1996/000122
International Filing Date 29.05.1996
IPC
C07C 319/14 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
319Preparation of thiols, sulfides, hydropolysulfides or polysulfides
14of sulfides
C07C 323/58 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
323Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
50containing thio groups and carboxyl groups bound to the same carbon skeleton
51having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
57the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
58with amino groups bound to the carbon skeleton
C25B 3/04 2006.01
CCHEMISTRY; METALLURGY
25ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
BELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON- METALS; APPARATUS THEREFOR
3Electrolytic production of organic compounds
04by reduction
CPC
C07C 319/14
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
319Preparation of thiols, sulfides, hydropolysulfides or polysulfides
14of sulfides
C07C 323/58
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
323Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
50containing thio groups and carboxyl groups bound to the same carbon skeleton
51having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
57the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
58with amino groups bound to the carbon skeleton
C25B 3/04
CCHEMISTRY; METALLURGY
25ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
BELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
3Electrolytic production of organic compounds
04by reduction
Applicants
  • DERIVADOS DEL ETILO, S.A. [ES]/[ES] (AllExceptUS)
  • ALDAZ RIERA, Antonio [ES]/[ES] (UsOnly)
  • CARMONA FLORES, Francisco [ES]/[ES] (UsOnly)
  • ESTEBAN MORALES, Manuel [ES]/[ES] (UsOnly)
  • GARCIA GARCIA, Vicente [ES]/[ES] (UsOnly)
  • GONZALEZ GARCIA, José [ES]/[ES] (UsOnly)
  • MONTIEL LEGUEY, Vicente [ES]/[ES] (UsOnly)
  • SANCHEZ CANO, Gaspar [ES]/[ES] (UsOnly)
Inventors
  • ALDAZ RIERA, Antonio
  • CARMONA FLORES, Francisco
  • ESTEBAN MORALES, Manuel
  • GARCIA GARCIA, Vicente
  • GONZALEZ GARCIA, José
  • MONTIEL LEGUEY, Vicente
  • SANCHEZ CANO, Gaspar
Agents
  • CARPINTERO LOPEZ, Francisco
Priority Data
P 950109801.06.1995ES
Publication Language Spanish (ES)
Filing Language Spanish (ES)
Designated States
Title
(EN) PROCESS FOR PRODUCING BY ELECTROCHEMICAL METHODS THIOETHERS FOR PHARMACEUTICAL USE
(ES) PROCEDIMIENTO PARA LA OBTENCION DE TIOETERES PARA USO FARMACEUTICO POR METODOS ELECTROQUIMICOS
(FR) PROCEDE D'OBTENTION DE THIOETHERS D'USAGE PHARMACEUTIQUE PAR DES METHODES ELECTROCHIMIQUES
Abstract
(EN)
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.
(ES)
Se obtienen tioéteres de fórmula (I): R1-S-R2, donde R1 es alquilo C2-C5, opcionalmente sustituído, fenilo sustituído, fenil(haloalquilo C1-C4), -CH2-COOR3, R3 es H o un catión, haloformilalquilo o haloformilarilo, y R2 es -(CH2)n-CH(NHR4)-COOH, R4 es H o acetilo y n es 1 o 2, mediante la electrorreducción de un disulfuro (II): R2-S-S-R2 en un medio básico al que se le adiciona un compuesto (III): R1-X, donde X es halógeno, de forma controlada, a lo largo del proceso, manteniendo el pH entre 9 y 12, en una célula electroquímica que comprende al menos, un cátodo y un ánodo, un catolito y un anolito separados por una membrana de intercambio iónico. Los tioéteres (I) obtenidos tienen actividad mucolítica, cumplen las especificaciones de la Farmacopea Europea y son adecuados para su empleo en farmacia.
(FR)
Le procédé permet d'obtenir des thioéthers de formule (I): R1-S-R2 dans laquelle R1 représente alkyle C2-C5 éventuellement substitué, phényle substitué, phényle(haloalkyle C1-C4), -CH2-COOR3, R3 représente H ou un cation, haloformylalkyle ou haloformylaryle, et R2 représente -(CH2)n-CH(NHR4)-COOH, R4 représente H ou acétyle et n vaut 1 ou 2, au moyen d'une électroréduction d'un bisulfure (II): R2-S-S-R2, dans un milieu basique auquel on ajoute un composé (III): R1-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.
Also published as
CZPV1997-246
KR1019970700640
RO97-00190
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