Potential antidepressants: 3-Methyl-6-dimethylamino-1,2-diphenylhexan-3-ol and related compounds

1987 ◽  
Vol 52 (10) ◽  
pp. 2564-2571
Author(s):  
Irena Červená ◽  
Jiří Holubek ◽  
Emil Svátek ◽  
Martin Valchář ◽  
Miroslav Protiva
Keyword(s):  
Amino Alcohol ◽  
Amino Alcohols ◽  
Related Compounds

3,4-Diphenylbutan-2-one (III) and 3-methyl-3-phenylbutan-2-one were transformed by treatment with 3-dimethylaminopropylmagnesium chloride and 1-methyl-4-piperidylmagnesium chloride to the amino alcohols VI, VII, and X. Compound VI was dehydrated to the olefinic amine VIII, and reduced to the saturated amine IX. 2-(3-Fluoro-4-hydroxyphenyl)ethylamine (XI) was prepared by a modified route via the methoxy precursor XV. Only the amino alcohol VI showed antireserpine activity in one test. The fluoro analogue of dopamine XI did show neither the dopaminomimetic nor the antidopaminergic character.

Antiaminic agents derived from thieno[2,3-c]-2-benzothiepin: 4-(1-Methyl-4-piperidylidene)-4,9-dihydrothieno[2,3-c]-2-benzothiepin and some related compounds

1983 ◽  
Vol 48 (2) ◽  
pp. 623-641 ◽  
Author(s):  
Zdeněk Polívka ◽  
Miroslav Rajšner ◽  
Jan Metyš ◽  
Jiří Holubek ◽  
Emil Svátek ◽  
...  
Keyword(s):  
Clinical Trials ◽  
Sulfuric Acid ◽  
Title Compound ◽  
Amino Alcohol ◽  
Hydrogen Sulfate ◽  
Geometric Isomers ◽  
Pure Alcohol ◽  
Acid Catalyzed ◽  
Anticataleptic Activity ◽  
Related Compounds

In the reaction of thieno[2,3c]-2-benzothiepin-4(9H)-one (VI) with 1-methyl-4-piperidylmagnesium chloride 7-(1-methyl-4-piperidyl)thieno[2,3-c]-2-benzothiepin-4(9H)-one (VIII) is formed in addition to the expected amino alcohol VII. The title compound I was obtained by the acid catalyzed dehydration of the pure alcohol VII. Compound I (pipethiadene) has outstanding antihistamine, antiserotonin, antireserpine and anticataleptic activity and was recommended to clinical trials as a potential antimigraine agent. For pharmacokinetic and metabolic studies there were prepared the NC2H3 analogue of pipethiadene IV and further, as potential metabolites, the demethyl analogue III, S-oxide X, demethyl S-oxide XI, N-oxide XIII and N,S-dioxide XIV. The Witting reaction of the ketone VI with 3-dimethylaminopropylidenetriphenylphosphorane resulted in a mixture of geometric isomers of 4-(3-dimethylamino-propylidene)-4,9-dihydrothieno[2,3-c]-2-benzothiepin with the strongly predominating Z-isomer XVI which was isolated from the mixture by crystallization of the hydrogen maleate. The mixture with the predominating Z-isomer XVI was converted by the treatment with 80% sulfuric acid and dilution with water to a mixture with the predominating E-isomer XV (dithiadene) which was isolated by crystallization of the hydrogen sulfate. Some further new thieno[2,3-c]-2-benzothiepin derivatives were synthesized as potential intermediates.

ChemInform Abstract: Synthesis of 1,2- and 1,4-Amino Alcohols from 1,3-Dienes via Oxazines. Rearrangements of 1,4-Amino Alcohol Derivatives to Oxazolines.

ChemInform ◽  
2010 ◽  
Vol 41 (37) ◽  
pp. no-no
Author(s):  
Lukas Werner ◽  
Jason Reed Hudlicky ◽  
Martina Wernerova ◽  
Tomas Hudlicky
Keyword(s):  
Amino Alcohol ◽  
Amino Alcohols

Tricyclic psychotropic agents containing two chalcogen atoms in the central ring: 8-Substituted 6-(4-piperidyl)-6H-dibenz[b,e]-1,4-oxathiepins

1982 ◽  
Vol 47 (11) ◽  
pp. 3077-3093 ◽  
Author(s):  
Karel Šindelář ◽  
Jiřina Metyšová ◽  
Jiří Holubek ◽  
Emil Svátek ◽  
Jiří Protiva ◽  
...  
Keyword(s):  
Secondary Amine ◽  
Amino Alcohol ◽  
Sodium Hydride ◽  
Amino Alcohols ◽  
Central Ring ◽  
Psychotropic Agents ◽  
High Degree ◽  
By Products ◽  
Antiapomorphine Effect ◽  
Central Depressant

2-(2-Fluorophenylthio)benzaldehydes IXa-c and 5-chloro-2-(2-fluorophenylthio)acetophenone were treated with 1-methyl-4-piperidylmagnesium chloride and 3-dimethylaminopropylmagnesium chloride, respectively, and the resulting amino alcohols VIa-c, XVII and XVIII were cyclized with sodium hydride in dimethylformamide. In addition to the title compounds Ia-c, XIX and XX, several types of by-products were obtained. Demethylation of compound Ib by the chloroformate method afforded the secondary amine IIb which was transformed to the amino alcohols IIIb and Vb. Compounds Ia-c are very potent neuroleptics with a high degree of central depressant and cataleptic activity. The amino alcohol Vb exhibits a very strong antiapomorphine effect in rats.

scholarly journals Continuous and convergent access to vicinyl amino alcohols

2015 ◽  
Vol 51 (82) ◽  
pp. 15133-15136 ◽  
Author(s):  
Tomoya Nobuta ◽  
Guozhi Xiao ◽  
Diego Ghislieri ◽  
Kerry Gilmore ◽  
Peter H. Seeberger
Keyword(s):  
Amino Alcohol ◽  
Amino Alcohols ◽  
Assembly System

A four module convergent chemical assembly system delivers two classes of vicinyl amino alcohol and five APIs.

Synthesis of 1,2-amino alcohols via catalytic C–H amidation of sp3 methyl C–H bonds

2014 ◽  
Vol 50 (81) ◽  
pp. 12073-12075 ◽  
Author(s):  
Taek Kang ◽  
Heejeong Kim ◽  
Jeung Gon Kim ◽  
Sukbok Chang
Keyword(s):  
Amino Alcohol ◽  
Amino Alcohols ◽  
Chelating Groups

A new route to 1,2-amino alcohols is presented by C–H amidation of sp3 methyl C–H bonds as a key step. Various alcohols were employed after converting them to removable ketoxime chelating groups. Iridium-catalyzed C–H amidation and following LAH reduction furnished β-amino alcohol products.

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