1-Halomethyl-6-phenyl-4H-s-[4,3-a][1,4]benzodiazepines

Details 1-Halomethyl-6-phenyl-4H-s-[4,3-a][1,4]benzodiazepines 1-Halomethyl-6-phenyl-4H-s-[4,3-a][1,4]benzodiazepines

1971-04-28

1979-02-27

Rollins, Alton D.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260239BD, 2602393D, 424269, C07D48704, A61K 3155

Patent

active

041419022

ABSTRACT:
1-Substituted-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepines of the formula II: ##STR1## wherein R.sub.0 is selected from the group consisting of hydrogen, methyl, ethyl, fluorine, chlorine, and bromine, and X is selected from fluorine, chlorine, and bromine; wherein R.sub.1 is selected from the group consisting of hydrogen, alkyl of 1 to 3 carbon atoms inclusive; wherein R.sub.2, R.sub.3, R.sub.4, and R.sub.5 are selected from the group consisting of hydrogen, alkyl, as defined above, halogen, nitro, cyano, trifluoromethyl, and alkoxy, alkylthio, alkylsulfinyl, and alkylsulfonyl, in which the carbon chain moieties are of 1 to 3 carbon atoms, inclusive, are prepared by reacting a compound of the formula: ##STR2## wherein R.sub.1, R.sub.2, R.sub.3 R.sub.4, and R.sub.5 are defined as above, with an haloacyl chloride or haloacyl bromide of the formula ##STR3## wherein R.sub.o and X are defined as above and X' is chlorine or bromine. The new products of formula II including their pharmacologically acceptable acid addition salts are useful as sedatives, tranquilizers and muscle relaxants in mammals and birds, and if X.dbd.X".dbd.Cl or Br they are useful as intermediates for cyano, alkylthio and dialkylamino products of high sedative and tranquilizing activity.

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