125605-13-2

Upstream product

• 7412-05-7 N-(1H-benzo[d]imidazol-2-yl)benzamide 
• 553-27-5 aniline mustard 

Downstream Products

• 125605-29-0 1,2,3,4,5,6-hexahydro-4-phenyl<1,3,6>triazocino<1,2-a>benzimidazole 
• 138490-71-8 N-[4-(5,6,9,10-Tetrahydro-8H-4b,7,10,11-tetraaza-cycloocta[a]indene-7-sulfonyl)-phenyl]-methanesulfonamide 

Relevant academic research and scientific papers

Class III Antiarrhythmic Activity of Novel Substituted 4-benzamides and Sulfonamides

The synthesis and Class III antiarrhythmic activity of a series of 4-benzamides and sulfonamides are described.Selected compounds shown a potent Class III activity and are devoid of effects on conduction both in vitro (dog Purkinje fibers) and in vivo (anesthetized dogs).Compounds having a 2-aminobenzimidazole group were found to be the most potent, and one compound having the heterocycle (5, WAY-123,398) was selected for further characterization.Compound 5 was shown to have good oral bioavailability and a favorable hemodynamic profile to produce a 3-fold increase of the ventricular fibrillation threshold and to terminate ventricular fibrillation, restoring sinus rhythm in anesthetized dogs.Voltage-clamp studies in isolated myocytes show that 5 is a potent and specific blocker of the delayed rectifier potassium current (IK) at concentrations that cause significant prolongation of action potential duration.

1,2,3,4,5,6-hexahydro[1,3,6]triazocino[1,1-a]benzimidazoles

Disclosed herein are novel 1,4-substituted-2,3,5,6-tetrahydro[1,3,6]triazocino[1,2-a]benzimidazole of Formulas I and II: STR1 wherein R1 may be phenyl, m- or p-nitrophenyl, m- or p-methylsulfonylaminophenyl, naphthyl, naphthyl mono-substituted by nitro or methylsulfonylamino, benzofurazanyl, 2-pyrimidinyl, 2- or 4-pyridinyl, 2- or 4-naphthyridinyl, pyrazinyl, isoquinolinyl, or quinolinyl; R2 may be hydrogen; C1 -C8 alkyl; C1 -C4 alkylphenyl or C1 -C4 alkyl-substituted-phenyl, in which phenyl may have one to three substituents selected from C1 -C4 alkyl, C1 -C4 alkoxy, fluorine, chlorine or bromine; phenyl or substituted-phenyl in which the phenyl substituents are the same as for c1 -C4 alkyl-substituted-phenyl; 2- or 4-pyrimidinyl; pyrazinyl; imidazolyl; C1 -C4 alkanoyl; halo or dihalo-(C1 -C4)alkanoyl, in which halo is fluoro or chloro; benzoyl or benzoyl substituted on the phenyl ring by one or two C1 -C4 alkyl groups; C1 -C4 alkanoyloxy; C1 -C4 alkylamino(C1 -C4)alkanoyl; C1 -C4 alkyloxycarbonyl; C1 -C4 alkylaminocarbonyl; phenylaminocarbonyl in which phenyl may have one to three C1 -C4 alkyl groups; phenyloxy or naphthyloxy(C1 -C4)alkyl in which the phenyl or naphthyl ring may be substituted by one to three C1 - C4 alkyl groups; C1 -C4 alkylsulfonyl; N-(C1 -C4) alkyl- or N-(C1 -C4) dialkylcarboxamido(C1 -C4)alkyl; N-phenyl or substituted phenyl-carboxamido(C1 -C4)alkyl in which phenyl may be substituted as above for C1 -C4 alkyl-substituted phenyl; cyano; amidino in which each N atom is substituted by a C1 -C4 alkyl group; and C1 -C4 alkylguanidino; and R3 and R4 are, independently, selected from hydrogen, C1 -C4 alkyl, C1 -C4 alkoxy, fluorine and chlorine, or acid addition salts thereof. Compounds of formulas I and II having certain values of R2 are antiarrhythmic or antiischaemic agents. The remaining values of R2 provide intermediate compounds of formulas I and II. Also disclosed herein a novel tetrahydro-3-substituted-7-substituted-1H-[1,2,5]triazepino[1,2-a][1,2,4]benzotriazines, wherein the 7 substituent may be --SMe, =S, =O, Cl or Br and the 3 substituent is the same as R2 in formulas I and II above. These componds also serve as intermediates for the production of the antiarrhythmic agents of formula II above.