Triazolo-benzodiazepine derivatives
AssigneeHoffmann-La Roche Inc.
InventorsQuirico Branca, Albert E. Fischli, Andre Szente
Life of this patent
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Abstract
There are presented compounds of the formula ##STR1## wherein R.sup.1 is a hydrogen atom or a lower alkyl group, R.sup.2 and R.sup.3 each are a hydrogen atom or a lower alkyl group, R.sup.4 is a halogen atom and either R.sup.5 is a hydrogen atom or a lower alkyl group and R.sup.6 is a lower alkyl or lower hydroxyalkyl group or R.sup.5 and R.sup.6 together with the nitrogen atom to which they are attached are a 3-membered to 7-membered heterocycle, and pharmaceutically acceptable acid addition salts thereof. The compounds and their salts are novel and possess valuable pharmacodynamic properties.
Claims15
A compound of the formula ##STR11## wherein R.sup.1 is a hydrogen atom or a lower alkyl group, R.sup.2 and R.sup.3 each are a hydrogen atom or a lower alkyl group, R.sup.4 is a halogen atom and either R.sup.5 is a hydrogen atom or a lower alkyl group and R.sup.6 is a lower alkyl or lower hydroxyalkyl group or R.sup.5 and R.sup.6 together with the nitrogen atom to which they are attached are a 3-membered to 7-membered heterocycle selected from the group consisting of aziridine, pyrrolidone and piperidine,
- and pharmaceutically acceptable acid addition salts thereof.
The compound:
- 1-[6-(o-Fluorophenyl)-1,4,4-trimethyl-4H-s-triazolo[4,3-a][1,4]-benzodiaze pin-8-yl]-3-(2-hydroxyethyl)urea.
The compound:
- 1-[6-(o-Chlorophenyl)-1,4,4-trimethyl-4H-s-triazolo[4,3-a][1,4]-benzodiaze pin-8-yl]-3-(2-hydroxyethyl)urea.
The compound:
- 3-[6-(o-Fluorophenyl)-4,4-dimethyl-4H-s-triazolo[4,3-a][1,4]benzodiazepin- 8-yl]-1,1-dimethylurea.
The compound:
- 3-[6-(o-Chlorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepin-8-yl]-1,1-dim ethylurea.
The compound:
- 3-[6-(o-Chlorophenyl)-1-methyl-4H-s-triazolo[4,3-a][1,4]benzodiazepin-8-yl ]-1,1-dimethylurea.
The compound:
- N-[6-(o-Chlorophenyl)-4,4-dimethyl-4H-s-triazolo[4,3-a][1,4]benzodiazepin- 8-yl]-1-pyrrolidinecarboxamide.
A compound selected from the group consisting of:
- 1-[6-(o-Fluorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepin-8-yl]-3-(2-hyd roxyethyl)urea,
- 3-[6-(o-fluorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepin-8-yl]-1,1-dime thylurea,
- 1-[6-(o-fluorophenyl)-1-methyl-4H-s-triazolo-[4,3-a][1,4]benzodiazepin-8-yl ]-3-(2-hydroxyethyl)urea,
- 3-[6-(o-fluorophenyl)-1,4,4-trimethyl-4H-s-triazolo[4,3-a][1,4]benzodiazepi n-8-yl]-1,1-dimethylurea,
- 1-[6-(o-chlorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepin-8-yl]-3-(2-hyd roxyethyl)urea,
- 1-[6-(o-chlorophenyl)-1-methyl-4H-s-triazolo[4,3-a]-[1,4]benzodiazepin-8-yl ]-3-(2-hydroxyethyl)urea,
- N-[6-(o-chlorophenyl)-1-methyl-4H-s-triazolo[4,3-a][1,4]benzodiazepin-8-yl] -1-pyrrolidinecarboxamide and
- N-[6-(o-fluorophenyl)-1,4,4-trimethyl-4H-s-triazolo[4,3-a][1,4]benzodiazepi n-8-yl]-1-pyrrolidinecarboxamide.
A compound of the formula ##STR12## wherein R.sup.1 is a hydrogen atom or a lower alkyl group, R.sup.2 and R.sup.3 each are a hydrogen atom or a lower alkyl group and R.sup.4 is a halogen atom.
A compound of the formula ##STR13## wherein R.sup.1 is a hydrogen atom or a lower alkyl group, R.sup.2 and R.sup.3 each are a hydrogen atom or a lower alkyl group, R.sup.4 is a halogen atom and either R.sup.53 is a protecting group and R.sup.63 is a lower alkyl group or a group of the formula
- --A--O--Y VIII
- in which A is a lower alkylene group and Y is a protecting group, or R.sup.53 is a hydrogen atom or a lower alkyl group and R.sup.63 is as above.
A compound of the formula ##STR14## wherein R.sup.1 is a hydrogen atom or a lower alkyl group, R.sup.2 and R.sup.3 each are a hydrogen atom or a lower alkyl group, R.sup.4 is a halogen atom, A is a lower alkylene group, R.sup.54 is a hydrogen atom or a lower alkyl group and L is a leaving group.
Dependencies are inferred from the claim text.