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 Imidazo[1,5-a][1,4]benzodiazepines

Details
Inventors: Walser, Armin; Fryer, Rodney I.; Benjamin, Louis;
Assignee: Hoffmann-La Roche Inc. (Nutley, NJ)
Primary Examiner: Trousof; Natalie
Assistant Examiner: Whittenbaugh; Robert C.
Attorney, Agent or Firm: Saxe; Jon S., Leon; Bernard S., Hoffman; Frank P.

Compounds are disclosed of the formula ##STR1## wherein R.sub.1 is hydrogen, halogen or trifluoromethyl; R.sub.2 is selected from the group consisting of lower alkylthio together with the sulfoxide and sulfone thereof, halo, lower alkylamino or lower alkoxy; Y is oxo or thio; R.sub.3 is selected from the group consisting of hydrogen, --COOR.sub.4 wherein R.sub.4 is hydrogen or lower alkyl, --CONR.sub.6 R.sub.5 wherein R.sub.5 and R.sub.6 are hydrogen or lower alkyl; X is hydrogen or halogen; and R.sub.7 is lower alkyl or hydrogen and the pharmaceutically acceptable salts and N-oxides thereof. Also presented are processes to produce the above compounds and intermediates therefor and derivatives thereof.

DETAILED DESCRIPTION We claim: 1.
A compound of the formula ##STR8## wherein R.
sub.
1 is hydrogen, halogen or trifluoromethyl; Y is oxo or thio; and X is hydrogen or halogen.




Description:
DESCRIPTION OF THE INVENTION The present invention relates to compounds of the formula ##STR2## wherein R.
sub.
1 is hydrogen, halogen or trifluoromethyl; R.
sub.
2 is selected from the group consisting of lower alkylthio together with the sulfoxide and sulfone thereof, halo, lower alkylamino or lower alkoxy; Y is oxo or thio; R.
sub.
3 is selected from the group consisting of hydrogen, --COOR.
sub.
4 wherein R.
sub.
4 is hydrogen or lower alkyl; --CONR.
sub.
6 R.
sub.
5 wherein R.
sub.
5 and R.
sub.
6 are hydrogen or lower alkyl; X is hydrogen or halogen; and R.
sub.
7 is lower alkyl or hydrogen and the pharmaceutically acceptable salts and N-oxides thereof.
As used in this disclosure, the term "lower alkyl" or "alkyl" comprehends both straight and branched chain (C.
sub.
1 to C.
sub.
7) carbon-hydrogen radicals, preferably C.
sub.
1 to C.
sub.
4 carbon-hydrogen radicals such as methyl, ethyl, propyl, isopropyl, butyl and the like.
The term "halogen" is used to include all four forms thereof, i.
e.
, chlorine, bromine, fluorine and iodine, The compounds of the present invention exhibit pharmacological activity as sedatives, muscle relaxants, anxiolytics and anticonvulsants.
The following reaction scheme sets forth the processes utilized to produce the novel compounds of the present invention.
##STR3## I.
fwdarw.
II Compounds of the formula I are known in the prior art.
Methods for their preparation are disclosed, for instance, in Belgian Pat.
No.
833,248 of Mar.
10, 1976.
The compound of formula I is reacted with phosgene in the presence of an acid acceptor, such as an organic or inorganic base, e.
g.
, pyridine, triethylamine, potassium carbonate or, preferably, a hydrogen chloride scavenger, such as 1,2-epoxy-3-phenoxypropane.
The reaction is effected at a temperature of between -50.
degree.
C.
to room temperature with 0



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