PROCESS FOR PRODUCING INDOLINE COMPOUNDS AND INTERMEDIATES FOR THE PRODUCTION OF THE SAME
申请人:TOKYO TANABE COMPANY LIMITED
公开号:EP0810214A1
公开(公告)日:1997-12-03
This invention concerns a method for the production of a 3-arylindoline compound represented by the general formula
(wherein R1 represents an optionally substituted phenyl group or an aromatic heterocyclic group and R2 represents a hydrogen atom, a halogen atom, a lower alkyl group, a hydroxy group, a lower alkoxy group, a carbamoyl group, or a lower alkoxycarbonyl group) which is used for the production of a 1-acyl-3-arylindoline compound represented by the general formula
(wherein R1 and R2 have the same meanings as defined above and R3 represents the following group)
which is the 5-HT3 receptor antagonist, based on the fact that a 1-acyl-3-arylindole compound obtained by having a removable electron withdrawing group linked thereto by acylating the 1 position of a 3-arylindole compound with such an organic acid as carboxylic acid or sulfonic acid easily undergoes a catalytic reduction under neutral or acidic conditions and gives rise to a 1-acyl-3-arylindoline compound and that an optically active 1-acyl-3-arylindole compound obtained by the acylation with an organic acid such as optically active carboxylic acid or sulfonic acid produces an optically active 1-acyl-3-arylindoline compound with high selectivity by the reaction of a catalytic reduction.
本发明涉及一种生产通式如下的 3-芳基吲哚啉化合物的方法
(其中 R1 代表任选取代的苯基或芳香杂环基团,R2 代表氢原子、卤素原子、低级烷基、羟基、低级烷氧基、氨基甲酰基或低级烷氧羰基)的方法,该方法用于生产由通式表示的 1-酰基-3-芳基吲哚啉化合物。
(其中 R1 和 R2 的含义与上述定义相同,R3 代表下列基团)
是 5-HT3 受体拮抗剂、通过用羧酸或磺酸等有机酸对 3-芳基吲哚化合物的 1 位进行酰化而得到的 1-酰基-3-芳基吲哚化合物,在中性或酸性条件下很容易发生催化还原反应,生成 1-酰基-3-芳基吲哚化合物。3-芳基吲哚化合物,而通过与有机酸(如具有光学活性的羧酸或磺酸)酰化得到的具有光学活性的 1-酰基-3-芳基吲哚化合物通过催化还原反应以高选择性生成具有光学活性的 1-酰基-3-芳基吲哚化合物。