Polarographic study of the substitution reactions of the chelates of triethyl-enetetraminehexa-acetic acid—I Reaction of the zinc chelate with calcium ions

Talanta ◽  
1968 ◽  
Vol 15 (12) ◽  
pp. 1457-1465 ◽  
Author(s):  
M Kopanica
Keyword(s):  
Acetic Acid ◽  
Calcium Ions ◽  
Polarographic Study ◽  
Substitution Reactions

Fluorinated tricyclic neuroleptics with prolonged action: 8-Methoxy, 8-ethoxy, 8-ethylthio and 8-hydroxy derivatives of 3-fluoro-10-(4-methylpiperazino)-10,11-dihydrodibenzo[b,f]thiepin

1982 ◽  
Vol 47 (5) ◽  
pp. 1382-1391 ◽  
Author(s):  
Jiří Jílek ◽  
Josef Pomykáček ◽  
Jiřina Metyšová ◽  
Miroslav Protiva
Keyword(s):  
Acetic Acid ◽  
Polyphosphoric Acid ◽  
Prolonged Action ◽  
Substitution Reactions ◽  
Methoxy Derivative ◽  
Chloro Derivatives ◽  
Boron Tribromide ◽  
Derivatives Of ◽  
Central Depressant ◽  
Boiling Toluene

Acids IIa-c were prepared by reactions of (4-fluoro-2-iodophenyl)acetic acid with 4-methoxythiophenol, 4-ethoxythiophenol and 4-(ethylthio)thiophenol and cyclized with polyphosphoric acid in boiling toluene to dibenzo[b,f]thiepin-10(11H)-ones IIIa-c. Reduction with sodium borohydride afforded the alcohols IVa-c which were treated with hydrogen chloride and gave the chloro derivatives Va-c. Substitution reactions with 1-methylpiperazine resulted in the title compounds Ia-c out of which the methoxy derivative Ia was transformed by demethylation with boron tribromide to the phenol Id. Compounds Ia-d are very potent neuroleptics exhibiting a clear prolongation of the central depressant and some prolongation of the cataleptic activity.

Reactions of N-substituted 2-aminopyridines with chloroacetyl chloride; Formation of a new series of heterocyclic betaines: 1-Substituted 4-chloromethyl-2-oxopyrido[1,2-a]pyrimidin-5-ium-3-olates

1989 ◽  
Vol 54 (5) ◽  
pp. 1376-1387 ◽  
Author(s):  
Hana Hulinská ◽  
Miloš Buděšínský ◽  
Jiří Holubek ◽  
Oluše Matoušová ◽  
Hana Frycová ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Sodium Borohydride ◽  
Nmr Spectra ◽  
Aqueous Ethanol ◽  
Hydrogen Bromide ◽  
Chloroacetyl Chloride ◽  
Gastric Lesions ◽  
Substitution Reactions ◽  
Reaction Compound ◽  
C Nmr

N-(2-Pyridyl)-2-chloroacetamide reacted with 1-methylpiperazine and gave the expected compound III. Attempts at preparing the N-substituted N-(2-pyridyl)-2-chloroacetamides by reactions of N-substituted 2-aminopyridines with chloroacetyl chloride in benzene in the presence of N,N-dimethylacetamide were negative and took an unexpected course. 2-Anilinopyridine and 2-(cyclohexylamino)pyridine afforded compounds which were identified by 1H and 13C NMR spectra as the heterocyclic betaines IVa and IVb. 2-(1-Butylamino)pyridine, 2-(benzylamino)pyridine and 2-(2-phenylethylamino)pyridine gave similarly compounds IVc-IVe. The chloromethyl compounds IVa-IVe underwent normal substitution reactions with 1-methylpiperazine and gave the methylpiperazino compounds Va-Ve. Attempts to reduce the betaines with sodium borohydride in aqueous ethanol proceeded in one case as the hydrogenolytic displacement of the chlorine atom with hydrogen (product VIa), in another case as ethanolysis (product VIIb). Formation of VIb by treatment of IVb with hydrogen bromide in boiling acetic acid is probably the result of a disproportionation reaction. Compound III (dimaleate VÚFB-17 103) was practically equipotent with pirenzepine (I) as an anti-ulcer agent in the test of indomethacine-induced gastric lesions in rats but was much weaker in tests for antocholinergic and antisecretory activity.

Potential metabolites of tricyclic neuroleptics: 2,8-Dihydroxy and 3,8-dihydroxy derivatives of 10-(4-methylpiperazino)-10,11-dihydrodibenzo[b,f]thiepin

1979 ◽  
Vol 44 (10) ◽  
pp. 2987-2996 ◽  
Author(s):  
Miroslav Protiva ◽  
Karel Šindelář ◽  
Zdeněk Šedivý ◽  
Josef Pomykáček
Keyword(s):  
Acetic Acid ◽  
Polyphosphoric Acid ◽  
Substitution Reactions ◽  
Piperazine Derivatives ◽  
Neuroleptic Agent ◽  
Boron Tribromide ◽  
Derivatives Of ◽  
Isomeric Acid ◽  
Central Depressant ◽  
Methoxybenzoic Acid

A synthesis of the title compounds II and III, potential metabolites of the neuroleptic agent perathiepin I, was carried out. A reaction of (2-iodo-5-methoxyphenyl)acetic acid with 4-methoxythiophenol afforded the acid VI. The isomeric acid XI was obtained from 2-iodo-4-methoxybenzoic acid by reaction with 4-methoxythiophenol and via intermediates VIII-X. Both acids (VI,XI) were cyclized with polyphosphoric acid to dimethoxydibenzo[b,f]thiepin-10(11H)-onesXIIab which were transformed via the alcohols XIIIab to the chloro compounds XIVab. Substitution reactions with 1-methylpiperazine gave the piperazine derivatives IV and V and dimethoxydibenzo[b,f]thiepins XVab. The dimethoxy compounds IV and V were demethylated with boron tribromide to the diaminodiphenols II and III. The central depressant and cataleptic activity of compounds II-V is lower than that of the unsubstituted substance I.

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