申请人:Schering Aktiengesellschaft
公开号:US04435403A1
公开(公告)日:1984-03-06
3-substituted beta-carbolines of the formula ##STR1## wherein R.sup.C is hydrogen, lower alkyl, alkoxyalkyl of up to 6 C-atoms, cycloalkyl of 3-6 C-atoms, aralkyl of up to 8 C-atoms, or (CH.sub.2).sub.n OR.sup.20 wherein R.sup.20 is alkyl of up to 6 C-atoms, cycloalkyl of 3-6 C-atoms or aralkyl of up to 8 C-atoms and n is an integer of 1 to 3; Y is oxygen, two hydrogen atoms or NOR.sup.1, wherein R.sup.1 is hydrogen, lower alkyl, aryl or aralkyl of up to 6 C-atoms, COR.sup.2, wherein R.sup.2 is lower alkyl of up to 6 C-atoms, or Y is CHCOOR.sup.3, wherein R.sup.3 is hydrogen or lower alkyl or Y is NNR.sup.4 R.sup.5, wherein R.sup.4 and R.sup.5 can be the same or different and each is hydrogen, lower alkyl, C.sub.6-10 -aryl, C.sub.7-10 -aralkyl or CONR.sup.6 R.sup.7, wherein R.sup.6 and R.sup.7 can be the same or different and each is hydrogen or lower alkyl or R.sup.4 and R.sup.5 together with the connecting N-atom, for a 5- or 6-membered heterocyclic ring which optionally may also contain an O-atom or up to 3 N-atoms and which optionally may be substituted by a lower alkyl group; Z is hydrogen, or alkoxy or aralkoxy each of up to 10 C-atoms and each optionally substituted by hydroxy, or Z is alkyl of up to 6 C-atoms, C.sub.6-10 -aryl or C.sub.7-10 -aralkyl each of which may optionally be substituted by a COOR.sup.8 -- or a CONR.sup.9 R.sup.10 group, wherein R.sup.8 is alkyl of up to 6 C-atoms, and R.sup.9 and R.sup.10 can be the same or different and each is hydrogen or alkyl of up to 6 C-atoms; or Z is NR.sup.9 R.sup.10, wherein R.sup.9 and R.sup.10 are as defined above; or Z is NR.sup.11 CHR.sup.12 R.sup.13, wherein R.sup.11 and R.sup.12 each is hydrogen or together form a N.dbd.C double bond, wherein R.sup.13 is C.sub.1-10 -alkyl or NR.sup.14 R.sup.15, wherein R.sup.14 and R.sup.15 are the same or different and each is hydrogen, OH or alkyl or alkoxy each of up to 6 C-atoms, or wherein R.sup.12 and R.sup.13 together are oxygen, in which case, R.sup.11 is hydrogen; or Z is COOR.sup.2 wherein R.sup.2 is as defined above; or Y and Z, together with the connecting C-atom, may form a 5- or 6-membered heterocyclic ring which contains an O-atom, adjoining O- and N-atoms or up to 4 N atoms and which optionally may be substituted by a lower alkyl group, hydroxy or oxo have valuable psychotropic properties which make them useful for example as tranquilizers.
该文描述的是一类化合物,即公式为##STR1##的3-取代β-咔啉,其中R.sup.C为氢、低碳基、长达6个碳原子的烷氧基、3-6个碳原子的环烷基、长达8个碳原子的芳基烷基或(CH.sub.2).sub.n OR.sup.20,其中R.sup.20为长达6个碳原子的烷基、3-6个碳原子的环烷基或长达8个碳原子的芳基烷基,n为1至3的整数;Y为氧、两个氢原子或NOR.sup.1,其中R.sup.1为氢、低碳基、长达6个碳原子的芳基或长达8个碳原子的芳基烷基、COR.sup.2,其中R.sup.2为长达6个碳原子的烷基,或Y为CHCOOR.sup.3,其中R.sup.3为氢或低碳基,或Y为NNR.sup.4R.sup.5,其中R.sup.4和R.sup.5可以相同也可以不同,每个都是氢、低碳基、C.sub.6-10-芳基、C.sub.7-10-芳基烷基或CONR.sup.6R.sup.7,其中R.sup.6和R.sup.7可以相同也可以不同,每个都是氢或低碳基,或R.sup.4和R.sup.5与连接的N原子一起形成一个5-或6-成员的杂环环,该环可以含有一个O原子或多达3个N原子,且可以选择性地被低碳基替换;Z为氢,或长达10个碳原子的烷氧基或芳基烷氧基,每个都可以选择性地被羟基取代,或Z为长达6个碳原子的烷基、C.sub.6-10-芳基或C.sub.7-10-芳基烷基,每个都可以选择性地被COOR.sup.8-或CONR.sup.9R.sup.10-基团取代,其中R.sup.8为长达6个碳原子的烷基,R.sup.9和R.sup.10可以相同也可以不同,每个都是氢或长达6个碳原子的烷基;或Z为NR.sup.9R.sup.10,其中R.sup.9和R.sup.10如上所定义;或Z为NR.sup.11CHR.sup.12R.sup.13,其中R.sup.11和R.sup.12每个都是氢或一起形成N.dbd.C双键,其中R.sup.13为C.sub.1-10-烷基或NR.sup.14R.sup.15,其中R.sup.14和R.sup.15可以相同也可以不同,每个都是氢、OH或长达6个碳原子的烷基或烷氧基,或者R.sup.12和R.sup.13一起是氧,此时R.sup.11为氢;或者Z为COOR.sup.2,其中R.sup.2如上所定义;或者Y和Z与连接的C原子一起可以形成一个含有一个O原子、相邻的O和N原子或多达4个N原子的5-或6-成员的杂环环,该环可以选择性地被低碳基、羟基或氧基取代。这些化合物具有有价值的精神药理特性,例如可以用作镇静剂。