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    Azepine derivatives
    85.
    发明授权
    Azepine derivatives 失效

    公开(公告)号：US3446798A

    公开(公告)日：1969-05-27

    申请号：US3446798D

    申请日：1965-06-21

    申请人： GEIGY CHEM CORP

    发明人： KUNG WERNER ,  PRINS DANIEL A

    IPC分类号： C07D223/22 ,  C07D223/24 ,  C07D223/28 ,  C07D41/08 ,  A61K27/00 ,  C07D57/00

    CPC分类号： C07D223/28 ,  C07D223/22 ,  C07D223/24

    摘要： The invention comprises compounds of the formula (in which X represents an ethylene or vinylene group, R represents a hydrogen atom or a C1- 4 acyl radical and R represents a C1- 4 alkyl group which contains more than 2 carbon atoms if R represents hydrogen and X ethylene, or the phenyl group, or, if R is an acyl radical, also the o- or p-nitrophenyl radical. The compounds are prepared by (a) reducing a 5-acyl-5H-dibenz[b,f]azepine - 3 - sulphonic acid chloride or its 10,11-dihydro derivative to a bis-(5-acyl-5H-dibenz[b,f]azepin - 3 - yl) - disulphide or its 10,11-dihydro derivative, and reacting these in the same step with an alkylating agent or with an o- or p-nitrophenyl halide to form a 3-alkyl-thio- or 3-(o- or 3-(p-nitro-phenylthio)-5-acyl - 5H - dibenz[b,f]azepine or the 10,11-dihydro derivative thereof, reducing a 3-(o-nitro- or 3-(p-nitrophenylthio)-5-acyl-5H-dibenz[b,f]azepine or the 10,11 dihydro derivative thereof to the corresponding 3-(o-amino) or 3-(p-amino-phenylthio) compound, converting this by diazotization and reduction into the corresponding 3-phenylthio - 5 - acyl - 5H - dibenz[b,f]azepine or the 10,11-dihydro derivative thereof and, if desired, hydrolysing a 3-alkylthio- or 3-phenylthio - 5 - acyl - 5H - dibenz[b,f]azepine or its 10,11-dihydro derivative obtained to a 3-alkylthio-or 3-phenylthio-5H-dibenz[b,f]azepine or its 10,11-dihydro derivative or, if desired, converting a 3-alkylthio or 3-phenylthio-10,11-dihydro - 5 - acyl - 5H - dibenz[b,f]azepine into a 3-alkylthio- or 3-phenylthio-5H-dibenz[b,f]azepine, or (b) diazotizing a 3-amino-5-acyl10,11 - dihydro - 5H - dibenz[b,f]azepine, reactin the resulting diazonium salt with thiophenol in an alkaline solution to form a 3-phenylthio-5-acyl - 10,11 - dihydro - 5H - dibenz[b,f]azepine and, if desired, hydrolysing the compound obtained to form 3-phenylthio-10,11-dihydro-5H - dibenz[b,f]azepine or converting a 3-phenylthio - 10,11 - dihydro - 5 - acyl - 5H - dibenz[b,f]azepine into 3 - phenylthio - 5H - dibenz[b,f]azepine. 3 - Chlorosulphonyl - 5 - acetyl - 5H - dibenz[b,f]azepine is prepared by diazotizing 3-amino-5-acetyl-5H-dibenz[b,f]azepine and treating the resulting diazonium salt with sulphur dioxide and cupric chloride. 3 - Methylthio - 5 - acetyl - 10 - (or 11 -) - bromo - 10,11 - dihydro - 5H - dibenz[b,f]azepine is prepared by treating 3-methylthio-5-acetyl-10,11-dihydro -dibenz[b,f]azepine with N-bromosuccinimide.