5h-2,3-benzodiazepine derivatives and a process for the...

C - Chemistry – Metallurgy – 07 – D

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C07D 243/02 (2006.01) C07D 311/76 (2006.01)

Patent

CA 1125749

ABSTRACT OF THE DISCLOSURE New 5H-2,3-benzodiazepine derivatives of the general formula (I), Image (I) wherein R stands for hydrogen atom, a C1-5 alkyl, dialkylaminoalkyl, amino, alkylamino or dialkylamino group, or aryl, phenyl- C1-3 alkyl or styryl group having optionally 1 to 3 halo- gen, hydroxy, acyloxy, methyl, trifluoromethyl, nitro, amino, methylenedioxy, C1-4 alkoxy and/or aralkoxy sub- stituent(s), or a heterocyclic group containing 1 or 2 nitrogen, oxygen and/or sulfur atom(s), R1 stands for hydrogen atom or a C1-4 alkyl, hydroxymethyl, formyl, carboxy, carbalkoxy, aryl or heterocyclic group, R2 stands for hydrogen atom or a C1-4 alkyl, dialkylamino- alkyl, alkylamino, dialkylamino or aryl group, and R3 and R4 each represent hydrogen atom, halogen atom, or a nitro, amino, hydroxy, acyloxy, C1-3 alkyl, C1-5 alkoxy, dialkylaminoalkoxy or aralkoxy group, or R3 and R4 may form together a methylenedioxy group or a carbonic acid residue, with the proviso that if R represents 3,4-dimethoxyphenyl group, R1 is methyl group and R2 is ethyl group, R3 and R4 may not stand for methoxy group, and pharmaceutically acceptable acid addition salts thereof 27231-62 - 2 - are prepared by reacting the appropriate 1,5-diketone com- pounds, 2-benzopyrilium salts, 6H-2-benzopyran-6-one derivatives or isochromene compounds with hydrazine, hydra- zine hydrate or a hydrazine C1-3 carboxylate. The new compounds according to the invention possess significant central nervous activities.

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