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1. AR054089 - SINTESIS DE DERIVADOS DE ACIDO FENOXIACETICO

Office
Argentina
Application Number P050104475
Application Date 26.10.2005
Publication Number 054089
Publication Date 06.06.2007
Publication Kind A1
IPC
C07C 69/734
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
69Esters of carboxylic acids; Esters of carbonic or haloformic acids
66Esters of carboxylic acids having esterified carboxyl groups bound to acyclic carbon atoms and having any of the groups OH, O-metal, -CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
73of unsaturated acids
734Ethers
C07C 69/736
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
69Esters of carboxylic acids; Esters of carbonic or haloformic acids
66Esters of carboxylic acids having esterified carboxyl groups bound to acyclic carbon atoms and having any of the groups OH, O-metal, -CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
73of unsaturated acids
734Ethers
736the hydroxy group of the ester being etherified with a hydroxy compound having the hydroxy group bound to a carbon atom of a six-membered aromatic ring
C07C 67/237
C07C 217/60
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
217Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
54having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
56with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
60linked by carbon chains having two carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
C07C 213/02
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
213Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
02by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
CPC
C07C 67/317
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
67Preparation of carboxylic acid esters
30by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
317by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
C07C 69/712
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
69Esters of carboxylic acids; Esters of carbonic or haloformic acids
66Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
67of saturated acids
708Ethers
712the hydroxy group of the ester being etherified with a hydroxy compound having the hydroxy group bound to a carbon atom of a six-membered aromatic ring
C07C 213/02
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
213Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
02by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
C07C 217/60
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
217Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
54having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
56with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
60linked by carbon chains having two carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
Applicants BOEHRINGER INGELHEIM INTERNATIONAL GMBH
Inventors WINTER, ERIC
REICHEL, CARSTEN
GUTHEIL, DIETER
Priority Data 04025432.8 26.10.2004 EP
Title
(ES) SINTESIS DE DERIVADOS DE ACIDO FENOXIACETICO
Abstract
(ES) Reivindicación 1: Método para la preparación de compuestos de fórmula general (1), o una sal de los mismos, en la que R1 es alquilo C1-6 ramificado o no ramificado o H; siendo preferiblemente alquilo C1-6 ramificado o no ramificado, entre los cuales se prefieren metilo, etilo, propilo, son más preferidos propilo, etilo y lo más preferido es etilo; X1 o X2 son independientemente uno de otro alquilo C1-6, preferiblemente metilo, etilo, propilo, más preferiblemente metilo, etilo y lo más preferiblemente metilo; que comprende las siguientes etapas: a) hacer reaccionar un compuesto de fórmula general (2), en la que X1 ó X2 son como se definió anteriormente y R2 son independientemente uno de otros alquilo C1-6 ramificado o no ramificado; siendo preferiblemente con alquilo C1-6, metilo, etilo, propilo, más preferiblemente metilo, etilo y lo más preferiblemente metilo; o ambos R2 juntos son un sistema de anillo saturado de 5 ó 6 miembros tal como 1,3-dioxanilo o 1,3 dioxolanilo; con un compuesto de fórmula general: ZCH2CO2R1, en la que Z representa un grupo de sustitución y R1 es como se definió anteriormente; b) transformar el compuesto de acuerdo con la etapa mencionada, que se representa por la fórmula general (3), con R1, R2, X1 y X2 como se definió anteriormente en un aldehído de fórmula general (4), en la que R1, R2, X1 y X2 como se definió anteriormente por: i) transformar el grupo hidroxilo libre de un compuesto de fórmula general (3) en un grupo saliente; y ii) retirar el grupo saliente generado previamente bajo condiciones reductoras; c) hacer reaccionar el aldehído de fórmula (4) así obtenido con 1-(4-hidroxi-fenil)-1-hidroxi-2-propilamina, preferiblemente, 4-hidroxi-norefedrina para dar el compuesto de fórmula general (1); y d) opcionalmente recristalizar el producto así obtenido; y/o e) opcionalmente transformar el producto en una forma de sal farmacológicamente aceptable como el hidrocloruro.