公开(公告)号：US3813415A

公开(公告)日：1974-05-28

申请号：US27626272

申请日：1972-07-28

申请人： GRODZISKIE ZAKLADY FARMA POLFA

发明人： KYCIA H ,  MICHNO Z ,  ZANIUK J ,  CHMIELEWSKA D ,  ROLAK H ,  LENKOWSKI P ,  KOBOSKO A ,  SURGIEWICZ J ,  STEFANIAK F

IPC分类号： C07D311/16 ,  C07D7/26

CPC分类号： C07D311/16

摘要： 3 - (BETA-DIALKYLAMINOETHYL) - 4-ALKYL-7-CARBOETHOXYMETHOXYCOUMARIN OF THE FORMULA:

3-(R2-N(-R3)-CH2-CH2-),4-R1,7-(C2H5-OOC-CH2-O-)-

2H-CHROMEN-2-ONE

IN WHICH R1, R2 AND R3 STAND FOR A LOWER ALKYL GROUP CONTAINING 1-3 CARBON ATOMS AND ITS HYDROHALIDES. THE ABOVE-MENTIONED COMPOUNDS PROVED TO BE DRUGS USED IN CASE OF CIRCULATORY SYSTEM DISEASES. THE SAID COMPOUNDS ARE PRODUCED IN THE REACTION OF RESORCINOL WITH A GAMMA-BUTYROLACTONE DERIVATIVE OF THE FORMULA:

3-(R1-CO-)TETRAHYDROFURAN-2-ONE

OR BY ADDITION OF A HYDROGEN HALIDE IN THE PRESENCE OF PHOSPHOROUS ACID (PIII) THEN THE THUS OBTAINED 3-(BETAHALOETHYL-4-ALKYL-7-HYDROXYCOUMARIN IS SUBJECTED TO REACTION WITH A HALOACETIC ACID ETHYL ESTER IN THE PRESENCE OF ALKALI METAL CARBONATE AND A CATALYTIC QUANTITY OF DIETHYLFORMAMIDE OR WATER AND POTASSIUM IODIDE. THE THUS OBTAINED 3-(BETA-HALOETHYL)-4-ALKYL-7-CARBOETHOXYMETHOXYCOUMARIN IS SUBJECTED TO REACTION WITH A DIALKYLAMINE AND THE THUS OBTAINED PRODUCT IS ISOLATED AS A COMPLEX COMPOUND WITH ZINC CHLORIDE AND IF NECESSARY CONVERTED TO THE HYDROHALIDE.