Dibenzoxazepine And Dibenzdiazepine Derivatives

Dibenzoxazepine and dibenzdiazepines do not structurally belong to any of the classes of drugs listed above. However, their mechanism of action, indications for use, and side effects are analogous to phenothiazine derivatives.

Loxapine: Loxapine, 2-chloro-11-(4-methyl-1-piperazinyl)dibenz [b,f][1,4]exazepine (6.5.3), which is synthesized from 2-(4-chlorophenoxy)anyline. Acylation of the resulting product using ethylchloroformate forms N-ethoxycarbonyl-2-(4-chlorophenoxy)aniline (6.5.2). Treatment of this product with a mixture of phosphorous oxychloride and phosphorous anhydride gives loxapine (6.5.3) [53-55].

Chlorpromazine Mech

Loxapine is a more expressed, active antipsychotic than chlorpromazine. Its sedative effect is inferior to that of chlorpromazine. Indications for its use and side effects correspond with those of phenothiazine derivatives. Loxapine is used for treating psychotic disturbances, in particular cases of chronic and severe schizophrenia. Synonyms of this drug are loxapac and loxitane.

Clozapine: Clozapine, 8-chloro-11-(4-methyl-1-piperazinyl)-5H-dibenzo[b,e] [1,4]diazepine (6.5.7) is synthesized by two methods. According to the first, 4-chloro-2-nitroaniline in the presence of copper filings is acylated by the o-chlorobenzoic acid methyl ester, forming the corresponding diphenylamine (6.5.4). By reacting this with N-methyl piperazine, the ester group in the resulting polyfunctional diphenylamine is transformed into the amide (6.5.5). The nitro group in the resulting 4-chloro-2- nitro-2'-carb-(N'-methyl piperazino)amide (6.5.5) is further reduced into an amine group by hydrogen in the presence of Raney nickel. Reacting the resulting product (6.5.6) with phosphorous oxychloride yields in heterocyclization into the desired dibenzodiazepine, clozapine (6.5.7) [56-58].

The other way of synthesis of clozapine is from 8-chloro-10,11-dihydro-5H-dibenzo[b,e]1, 4-diazepin-11-thione, which is alkylated at the sulfur atom of the dibenzodiazepine ring by 4-nitrobenzylchloride in the presence of potassium ieri-butoxide, giving N-methyl derivative (6.5.8). Reaction of this with N-methylpiperazine gives the desired clozapine (6.5.7) [59].

Clozapine is a neuroleptic, which expresses antipsychotic and sedative action. It does not cause general depression and extrapyramidal disorders. It is used for severe and chronic forms of schizophrenia, maniacal conditions, manic-depressive psychosis, psychomotor excitement, and various other psychotic conditions. Synonyms of this drug are leponex, iprox, and others.

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