Synthetic Utilization of Polynitroaromatic Compounds. 3. Preparation of Substituted Dibenz[b,f][1,4]oxazepine-11(10H)-ones from 2,4,6-Trinitrobenzoic Acid via Nucleophilic Displacement of Nitro Groups

Q2 · CHEMISTRY

Article

Author: Samet, Alexander V. ; Chernysheva, Natalya B. ; Kislyi, Konstantine A. ; Strelenko, Yuri A. ; Marshalkin, Victor N. ; Semenov, Victor V.

[Reaction: see text]. 1,3-dinitrodibenz[b,f][1,4]oxazepin-11(10H)-one, prepared by intramolecular displacement of nitro group in N-(2-hydroxyphenyl)-2,4,6-trinitrobenzamide, reacts with O- and S-nucleophiles to yield the products of mono- or bis-substitution of the nitro groups. The nitro group in position 3 is displaced first. This observation is in contrast with earlier results for the nitro-substituted benzoannulated five-membered heterocycles. This difference in reactivity is likely due to the increased steric hindrance for peri-nitro group displacement in the case of the benzoannulated seven-membered heterocycle. N-Alkylation of the nitro-substituted dibenz[b,f][1,4]oxazepin-11(10H)-ones yields analogues of a known antidepressant drug Sintamil. The structure of the products is confirmed by NOE experiments and alternative synthesis.

01 Jul 1995·Indian journal of physiology and pharmacology

Effects of nitroxazepine on diastolic blood pressure in mild hypertensive patients--a short term clinical study.

Article

Author: Deshpande, A M ; Balani, N D ; Parhate, S M ; Thawani, V R

In a double blind short term clinical study, nitroxazepine has been found to be superior over placebo in reducing the diastolic blood pressure in mild hypertensive patients. In short term open clinical trial design nitroxazepine (25 mg PO, HS) has been found to be superior and better tolerated than diazepam (5 mg PO, HS). In open clinical trial design, nitroxazepine (25 mg PO, HS) reduced the diastolic blood pressure to the target level (100 mm Hg and less) effectively controlling the uncontrolled hypertensive patients receiving maintenance dose of beta blockers. There was no such beneficial effect in patients receiving maintenance doses of other antihypertensive drugs (pilot study). Adverse drug reactions like disturbed sleep in one, uneasiness in 3, palpitation in one and dryness of mouth in one patient have been observed.

01 Apr 1991·Indian journal of psychiatryQ4 · MEDICINE

Pharmacokinetics of nitroxazepine in depressed patients.

Q4 · MEDICINE

ArticleOA

Author: Bakshi, R ; Shah, L P ; Gupta, K C ; Nandkarni, A M ; Bhatia, S C ; Vaidya, A B ; Shah, S J ; Doshi, K J ; Bhatt, A D

A pharmacokinetic study was done on 10 depressed patients (DSM-III-R 296.3). The patients were treated with Sintamil (R) (nitroxazepine HCl) with titrated dose from 75 mg to 225 mg for 6 weeks. Plasma levels of nitroxazepine (Sintamil (R)) and its metabolites desmethyl (D), N-oxide (N-O) and carboxylic acid (c) were estimated. Anti-depressant efficacy was judged by reduction in Hamilton Rating Depression Scale (HDRS) scores, and tolerability was monitored by reports of unwanted effects.The overall reduction in HDRS score was about 50% by 6 weeks. The plasma levels of nitroxazepin (ng/ral) showed a rise from a mean ( +SEM) level. 47.0 4-7.3 on day 1 (dose 75 mg) to 129.84-24.6 on day 7 (dose 150 mg) (p< 0.01) and remained steady till day 21. There were large interindividual variations. The metabolites followed a similar pattern. The HDRS score showed a steady reduction between day 14 and 42 when the levels of nitroxizepine and des-methyl metabolites were maintained between 176.5 ng/ml to 251 ng/ml.

100 Deals associated with Nitroxazepine hydrochloride

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