Substitution reactions of N-phenylmercuriocycloazaheptathiane and related compounds

1976 ◽  
pp. 237 ◽  
Author(s):  
Robert J. Ramsay ◽  
Henry G. Heal ◽  
Henri Garcia-Fernandez
Keyword(s):  
Substitution Reactions ◽  
Related Compounds

Noncataleptic neuroleptic agents: 2-(4-(2-(2-Chloro-10,11-dihydrodibenzo[b,f]thiepin-10-yloxy)ethyl)piperazine-1-yl)ethanol and some related compounds

1988 ◽  
Vol 53 (11) ◽  
pp. 2731-2741 ◽  
Author(s):  
Jiří Jílek ◽  
Martin Valchář ◽  
Jiří Holubek ◽  
Nataša Dlohožková ◽  
Josef Pomykáček ◽  
...  
Keyword(s):  
Preclinical Studies ◽  
Acid Chlorides ◽  
Substitution Reactions ◽  
Related Compounds

10-(2-Bromoethoxy)-2-chloro-10,11-dihydrodibenzo[b,f]thiepin (X), prepared by two methods, was subjected to substitution reactions with 2-(1-piperazinyl)ethanol, 3-(1-piperazinyl)propanol, 1-methylpiperazine, 3-(1-piperazinyl)propionamide, piperazine, and 1-(ethoxycarbonyl)piperazine and gave the title compounds II-VII. The alcohol II was esterified by treatment with acid chlorides to compounds VIII and IX. Compounds II, V, and VIII proved to be noncataleptic neuroleptic agents and II (clopithepin, VÚFB-17 076) was selected for preclinical studies.

6a-Thiathiophthens and related compounds. Part II. Substitution reactions

1971 ◽  
pp. 963 ◽  
Author(s):  
R. J. S. Beer ◽  
D. Cartwright ◽  
R. J. Gait ◽  
D. Harris
Keyword(s):  
Substitution Reactions ◽  
Related Compounds

Potential hypnotics and anxiolytics in the 4H-s-triazolo[4,3-a]-1,4-benzodiazepine series: 8-Chloro-6-(2-chlorophenyl)-1-[4-(2-methoxyethyl)piperazino]-4H-s-triazolo[4,3-a]-1,4-benzodiazepine and some related compounds

1983 ◽  
Vol 48 (8) ◽  
pp. 2395-2410 ◽  
Author(s):  
Zdeněk Polívka ◽  
Miroslav Ryska ◽  
Jiří Holubek ◽  
Emil Svátek ◽  
Jan Metyš ◽  
...  
Keyword(s):  
Title Compound ◽  
Substitution Reaction ◽  
Gradual Decrease ◽  
Substitution Reactions ◽  
Bromo Derivative ◽  
Related Compounds ◽  
Very High

1-Bromo derivatives XIIa and XIIb were prepared by bromination of 8-chloro-6-phenyl-4H-s-triazolo[4,3-a]-1,4-benzodiazepine (XIa) and its 6-(2-chlorophenyl) analogue XIb with bromine in chloroform in the presence of pyridine. Substitution reactions with 1-(2-methoxyethyl)piperazine (XIVb), 1-(3-methoxypropyl)piperazine (XVb), 1-(2-ethoxyethyl)piperazine (XVIb) and 1-(2-methylthioethyl)piperazine (XVIIb) afforded the title compound IIb and analogues IIa and IIIb-Vb. A substitution reaction of the bromo derivative XIIb with piperazine gave the 1-piperazino derivative VIIIb which was alkylated with 2-phenoxyethyl bromide and 2-phenylthioethyl bromide to give compounds VIb and VIIb. The title compound IIb has very high anticonvulsant and discoordinating activities in mice. The enlargement of the substituent R1 (compounds IIIb-VIIb) results in a gradual decrease of the effects mentioned.

Potential hypnotics and anxiolytics: Synthesis of 2-bromo-4-(2-chlorophenyl)-9-[4-(2-methoxyethyl)piperazino]-6H-thieno[3,2,4-triazolo[4,3-a]-1,4-diazepine and of some related compounds

1984 ◽  
Vol 49 (3) ◽  
pp. 621-636 ◽  
Author(s):  
Zdeněk Polívka ◽  
Jiří Holubek ◽  
Emil Svátek ◽  
Jan Metyš ◽  
Miroslav Protiva
Keyword(s):  
Title Compound ◽  
Point Of View ◽  
Triethyl Orthoformate ◽  
Substitution Reactions ◽  
Bromo Derivative ◽  
Anticonvulsant Activities ◽  
Related Compounds

The synthesis of 2,9-dibromo-4-(2-chlorophenyl)-6H-thieno[3,2-f]-1,2,4-triazolo[4,3-a]-1,4,diazepine (XX) has been carried out. The substitution reactions of XX with 1-(2-methoxyethyl) piperazine, 1-(3-methoxypropyl)piperazine, 1-(2-ethoxyethyl)piperazine and 1-(2-methylthiothyl)-piperazine afforded the title compound XXIV and its analogues XXV-XXVII. N-Alkylations of 2-bromo-4-(2-chlorophenyl)-9-piperazino-6H-thieno[3,2-f]-1,2,4-triazolo[4,3-a]-1,4-diazepine (XXIII) with 2-phenoxyethyl bromide and 2-phenylthioethyl bromide gave compounds XXVIII and XXIX. Cyclization of 5-(2-chlorophenyl)-2-hydrazino-3H-thieno[2,3-e]-1,4-diazepine(XVIIIa) by treatment with triethyl orthoformate resulted in 4-(2-chlorophenyl)-6H-thieno[3,2-f]-1,2,4-triazolo[4,3-a]-1,4-diazepine (XIX) which could be brominated only to the 9-bromo derivative XXI; attempts at further bromination to position 2 were unsuccessful. Some contribution to the syntheses of etizolam (I) and its dechloro analogue V in the stage of intermediates are being described. Compounds XXIV-XXIX were pharmacologically tested from the point of view of discoordinating and anticonvulsant activities; they proved less active than the analogous 8-chloro-6-(2-chlorophenyl)-1-piperazino-4H-striazolo[4,3-a]-1,4-benzodiazepines.

Neuroleptic agents derived from perathiepin: 6,7-Dichloro derivative of 10-(4-methylpiperazino)-10,11-dihydrodibenzo[b,f]thiepin and related compounds

1981 ◽  
Vol 46 (7) ◽  
pp. 1607-1613 ◽  
Author(s):  
Jiří Jílek ◽  
Josef Pomykáček ◽  
Jiřina Metyšová ◽  
Miroslav Protiva
Keyword(s):  
Benzoic Acid ◽  
Title Compound ◽  
Titanium Tetrachloride ◽  
Substitution Reactions ◽  
Related Compounds ◽  
Hydroxyethyl Piperazine ◽  
Central Depressant ◽  
Dichloro Derivative ◽  
Iodobenzoic Acid

The reaction of 2,3-dichlorothiophenol with 2-iodobenzoic acid gave 2-(2,3-dichlorophenylthio)benzoic acid (V) which was transformed in four steps to the homological acid IX. Cyclization resulted in 6,7-dichlorodibenzo[b,f]thiepin-10(11H)-one (X) which was converted via the alcohol XI to the trichloro compound XII. Substitution reactions of XII with 1-methylpiperazine and 1-(2-hydroxyethyl)piperazine afforded the title compound I and its hydroxyethyl analogue II. Reaction of the ketone X with 1-methylpiperazine and titanium tetrachloride gave the enamine III. Compounds I-III exhibit mild central depressant and relatively strong cataleptic activity.

1-(3-Dimethylamino-1-phenylpropyl)piperazines and related compounds: Synthesis and pharmacological screening

1981 ◽  
Vol 46 (11) ◽  
pp. 2729-2733 ◽  
Author(s):  
Jiří Jílek ◽  
Josef Pomykáček ◽  
Jiří Němec ◽  
Miroslav Protiva
Keyword(s):  
Short Duration ◽  
Secondary Amine ◽  
Thionyl Chloride ◽  
Local Anaesthetic ◽  
Antiarrhythmic Action ◽  
Substitution Reactions ◽  
Pharmacological Screening ◽  
Hydrolysis Of ◽  
Related Compounds ◽  
Antiarrhythmic Effects

Substitution reactions of N,N-dimethyl-3-chloro-3-phenylpropylamine with 1-methylpiperazine and a series of analogues afforded 1-(3-dimethylamino-1-phenylpropyl)piperazines I-V. A similar substitution with piperidine resulted in the diamine VIII. Hydrolysis of the carbamate V gave the secondary amine VI which was transformed by alkylation with cyclopropylmethyl bromide to compound VII. 3-Dimethylamino-3-phenylpropanol was treated with thionyl chloride to give N,N-dimethyl-3-chloro-3-phenylpropylamine (IX) which reacted with 1-methylpiperazine and afforded the triamine X. The maleates of the amines prepared exhibited hypotensive effects of short duration (III, IV, VI, VII, X) and moderate antiarrhythmic effects (V-VIII). The phenylpiperazine derivative III showed a significant antiarrhythmic action and a high local anaesthetic activity.

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