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Home Vasodialators Intermediates-for-triazolobenzazepines

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 Intermediates for triazolobenzazepines

Details
Inventors: Fryer, Rodney I.; Trybulski, Eugene J.; Walser, Armin;
Assignee: Hoffmann-La Roche Inc. (Nutley, NJ)
Primary Examiner: Rollins; Alton D.
Assistant Examiner:
Attorney, Agent or Firm: Saxe; Jon S., Leon; Bernard S., Hoffman; Frank P.

There is presented triazolobenzazepines of the formula ##STR1## wherein R.sub.1 is hydrogen or lower alkyl and X and Y are hydrogen or halogen and the pharmaceutically acceptable salts thereof. Also disclosed are novel processes and intermediates leading to the triazolobenzazepines. The triazolobenzazepines are useful compounds having anxiolytic, sedative, muscle relaxant and anticonvulsant activity.

DETAILED DESCRIPTION What is claimed: 1.
A compound of the formula ##STR6## wherein X and Y are hydrogen or halogen.




Description:
DESCRIPTION OF THE INVENTION The present invention relates to triazolobenzazepines of the formula ##STR2## wherein R.
sub.
1 is hydrogen or lower alkyl and X and Y are hydrogen or halogen and the pharmaceutically acceptable salts thereof.
Particularly preferred compounds are those wherein X is chloro, Y is hydrogen, chloro or fluoro and R.
sub.
1 is hydrogen or methyl with the 2-position as preferred for the methyl substituent along with the 3-position.
As used herein, the term "lower alkyl" means a branched or straight chain hydrocarbon radical of C.
sub.
1 to C.
sub.
7 length with C.
sub.
1 to C.
sub.
4 as preferred, e.
g.
, methyl, ethyl, isopropyl, butyl, etc.
As used herein, the term "halogen" means all four forms thereof, i.
e.
, chloro, bromo, iodo and fluoro.
The following set forth the reaction scheme utilized to produce the novel end products: ##STR3## wherein X and Y are as above ##STR4## wherein X and Y are as above ##STR5## wherein R.
sub.
1, X and Y are as above I.
fwdarw.
II and IIA The compound of formula I is a previously disclosed compound, see U.
S.
Patent Application Ser.
No.
10,118, and may be produced following the teaching set forth in Examples 17 to 26.
The compound of formula I may be reacted with an alkali metal azide, such as, sodium or potassium azide and a lower alkyl carboxylic acid, such as, acetic or propionic acid, in a polar aprotic solvent, such as, dimethylsulfoxide or dimethylformamide.
The reaction temperature may be varied from about room temperature to about 110.
degree.
C.
with the particular preferred temperature chosen dependent on the substitution pattern of the moieties X and Y.
The byproduct IIA is thereafter isolated and discarded.
II.
fwdarw.
III The compound of formula II is thereafter reacted with an aqueous solution of a lower alkyl amine, e.
g.
, methyl amine.
A C.
sub.
1 to C.
sub.
4 alcohol is utilized as the solvent with ethanol as preferred



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