Potential antipsychotic agents. 5. Synthesis and antidopaminergic properties of substituted 5,6-dimethoxysalicylamides and related compounds

1990 ◽  
Vol 33 (4) ◽  
pp. 1155-1163 ◽  
Author(s):  
Thomas Hoegberg ◽  
Stefan Bengtsson ◽  
Tomas De Paulis ◽  
Lars Johansson ◽  
Peter Stroem ◽  
...  
Keyword(s):  
Antipsychotic Agents ◽  
Related Compounds

1-[3-(Diarylamino)propyl]piperidines and Related Compounds, Potential Antipsychotic Agents with Low Cataleptogenic Profiles

1985 ◽  
Vol 28 (5) ◽  
pp. 606-612 ◽  
Author(s):  
Lawrence D. Wise ◽  
Ian C. Pattison ◽  
Donald E. Butler ◽  
Horace A. DeWald ◽  
Edward P. Lewis ◽  
...  
Keyword(s):  
Antipsychotic Agents ◽  
Related Compounds

ChemInform Abstract: Potential Antipsychotic Agents. Part 5. Synthesis and Antidopaminergic Properties of Substituted 5,6-Dimethoxysalicylamides and Related Compounds.

ChemInform ◽  
1990 ◽  
Vol 21 (48) ◽  
Author(s):  
T. HOEGBERG ◽  
S. BEGTSSON ◽  
T. DE PAULIS ◽  
L. JOHANSSON ◽  
P. STROEM ◽  
...  
Keyword(s):  
Antipsychotic Agents ◽  
Related Compounds

Potential antipsychotic agents: 2-Chloro- and 2-methyl-11-(2-piperazinoethoxy)-6,11-dihydrodibenzo[b,e]thiepins and some related compounds; Synthesis and pharmacology

1984 ◽  
Vol 49 (11) ◽  
pp. 2520-2530 ◽  
Author(s):  
Václav Bártl ◽  
Karel Šindelář ◽  
Vladimír Valenta ◽  
Jiří Holubek ◽  
Emil Svátek ◽  
...  
Keyword(s):  
Sulfuric Acid ◽  
Alkaline Hydrolysis ◽  
Antipsychotic Agents ◽  
Similar Reaction ◽  
Substitution Reactions ◽  
Single Product ◽  
Hydrolysis Of ◽  
Related Compounds ◽  
Hydroxyethyl Piperazine ◽  
Neuroleptic Activity

Reactions of 2-chloro- and 2-methyl-6,11-dihydrodibenzo[b,e]thiepin-11-ol with 2-bromoethanol in the presence of sulfuric acid in boiling benzene afforded the 2-bromoethyl ethers VIa and VIb which were transformed by substitution reactions with 1-methylpiperazine, 1-(2-hydroxyethyl)-piperazine and 1-(ethoxycarbonyl)piperazine to the title compounds. Alkaline hydrolysis of the carbamate IVa gave the secondary amine IIIa. Treatment of the bromo ether VIa with 4-(4-chloro-3-trifluoromethylphenyl)piperidin-4-ol resulted in the piperidine derivative VIIa. Substitution reaction of 11-chloro-6,11-dihydrodibenzo[b,e]thiepin with 1-(2-methoxyethyl)piperazine and 1-(2-ethoxyethyl)piperazine led to the amino ethers VIII and IX. Reaction of 11-chloro-11-phenyl-6,11-dihydrodibenzo[b,e]thiepin with 2-dimethylaminoethanethiol in dimethylformamide at 90°C gave a mixture of two isomeric bases which was separated to the expected sulfide X and the base XII, resulting evidently after the rearrangement of the primary carbocation. A similar reaction of 3-dimethylaminopropanethiol afforded a single product of structure XI. Out of the compounds prepared, the ether VIII was found most interesting: it is little toxic and has significant antireserpine activity in two tests (is considered a potential antidepressant). The ethers Iab, Iab, IIIa and VIIa did not reveal the expected neuroleptic activity.

ChemInform Abstract: 1-(3-(DIARYLAMINO)PROPYL)PIPERIDINES AND RELATED COMPOUNDS, POTENTIAL ANTIPSYCHOTIC AGENTS WITH LOW CATALEPTOGENIC PROFILES

1985 ◽  
Vol 16 (34) ◽  
Author(s):  
L. D. WISE ◽  
I. C. PATTISON ◽  
D. E. BUTLER ◽  
H. A. DEWALD ◽  
E. P. LEWIS ◽  
...  
Keyword(s):  
Antipsychotic Agents ◽  
Related Compounds

11-(3-[4-(2-Hydroxyethyl)piperazino]propylidene)-6,11-dihydrodibenzo[b,e]thiepin, its 2-chloro derivative and some related compounds as potential antipsychotic agents; Synthesis and pharmacology

1984 ◽  
Vol 49 (8) ◽  
pp. 1816-1826 ◽  
Author(s):  
Václav Bártl ◽  
Emil Svátek ◽  
Antonín Dlabač ◽  
Stanislav Wildt ◽  
Miroslav Protiva
Keyword(s):  
Acetic Anhydride ◽  
Amino Alcohol ◽  
Substitution Reaction ◽  
Antipsychotic Agents ◽  
Substitution Reactions ◽  
Chloro Derivative ◽  
Cns Effects ◽  
Related Compounds ◽  
Depot Antipsychotics ◽  
Hydroxyethyl Piperazine

Substitution reactions of (E)-11-(3-bromopropylidene)-6,11-dihydrodibenzo[b,e]thiepin (VIIIa) and its 2-chloro derivative VIIIb with 1-(2-hydroxyethyl)piperazine gave the title compounds IIIa and IIIb which afforded by treatment with acetic anhydride, decanoyl chloride and 3,4,5-trimethoxybenzoyl chloride the esters IVab-VIab. Reduction of the olefinic compounds IIIa and IIIb with hydrolytic acid resulted in the saturated amines IXa and IXb. The piperazine derivativeX was obtained by a substitution reaction of 2,11-dichloro-6,11-dihydrobenzo[b,e]thiepin with 1-(2-hydroxyethyl)piperazine. The amino alcohols IIIa and IIIb, as well as their acetates and 3,4,5-trimethoxybenzoates, are almost devoid of the CNS effects. The decanates Va and Vb have not the properties of the depot antipsychotics (neither antidepressants, nor neuroleptics). The saturated amino alcohol IXa showed some antihistamine, spasmolytic and adrenolytic effects.

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