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 Oxadiazolotriazine derivatives

Details
Inventors: Muller, Jean-Claude; Ramuz, Henri;
Assignee: Hoffmann-La Roche Inc. (Nutley, NJ)
Primary Examiner: Ford; John M.
Assistant Examiner:
Attorney, Agent or Firm: Saxe; Jon S., Leon; Bernard S., Isgro; William G.

Oxadiazolotriazine derivatives of the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are as hereinafter set forth, are described. A process for preparing compounds of formula I wherein R.sup.1 is hydrogen, R.sup.2 is a group of the formula --COOR.sup.5, wherein R.sup.5 is as hereinafter set forth, and R.sup.3 is as hereinafter set forth, by cyclizing an intermediate of the formula ##STR2## wherein R.sup.3 and R.sup.5 are as hereinafter set forth, is also described. The compounds of formula I are useful in the treatment of vascular-condition hypertension or also as vasodilators in the case of peripheral blood supply disorders.

DETAILED DESCRIPTION OF THE INVENTION The oxadiazolotriazine derivatives of the invention are compounds of the formula ##STR5## wherein R.
sup.
1 is hydrogen and R.
sup.
2 is a group of the formula ##STR6## --COOR.
sup.
5 or --CH(R.
sup.
6)COOR.
sup.
7, or R.
sup.
1 and R.
sup.
2 are the same and are hydrogen or a group of the formula --CH(R.
sup.
6)COOR.
sup.
7, R.
sup.
3 is diallylamino or 1,2,5,6-tetrahydropyridinl-yl, R.
sup.
4 is alkyl, haloalkyl, alkoxyalkyl, aryloxyalkyl, aralkyloxyalkyl, aralkyl, alkoxycarbonylalkyl, aryl, a group of the formula --C(R.
sup.
8).
dbd.
CH(R.
sup.
9), an alkoxycarbonylalkylcarbonyl, or a 4-membered to 7-membered heterocyclic group which is optionally bound via a methylene group, R.
sup.
5 is alkyl, alkoxyalkyl, aralkyl, aryl or allyl, R.
sup.
6 is hydrogen or alkyl, R.
sup.
7 is alkyl and R.
sup.
8 and R.
sup.
9 each are alkyl, aryl or aralkyl or a 4-membered to 7-membered heterocyclic group, or a salt thereof with a pharmaceutically acceptable base.
The term "alkyl" as used herein, alone or in combination, denotes a straight-chain and branched-chain saturated hydrocarbon group of 1-8 carbon atoms, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert.
butyl, or the like.
The term "alkoxy" denotes an alkyl ether wherein the "alkyl" moiety is as described above.
The term "haloalkyl" denotes an alkyl group wherein one or more of the hydrogen atoms has been replaced by "halogen".
The term "halogen" denotes fluorine, chlorine, bromine or iodine.
The term "aryl" denotes mononuclear or dinuclear aromatic groups of up to 12 carbon atoms in which one or more of the hydrogen atoms can be replaced by alkyl, alkoxy, halogen, cyano, nitro, alkanoyloxy or alkoxycarbonyl, for example, phenyl, halophenyl, dihalophenyl, methoxyphenyl, dimethoxyphenyl, nitrophenyl, tolyl, methoxycarbonylphenyl, naphthyl and the like.
The term "aryloxy" denotes an aryl ether group in which the "aryl" moiety is as previously described.
The term "aralkyl" denotes an aryalkyl group such as benzyl, phenethyl and the like



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