49640-12-2Relevant academic research and scientific papers
N,N'-BIS[2-3-SUBSTITUTED-4-HYDROXYPHENYL)-2-HYDROXYETHYL)]-POLYMETHYLENEDIAMINES
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, (2008/06/13)
N,N'-Bis 2-(3-substituted-4-hydroxyphenyl)-ethyl or-2-hydroxyethyl!-polymethylenediamines having β-adrenergic stimulant activity particularly as selective bronchodilators, are prepared generally by condensation of an N-benzylphenethylamine with a polymethylene dihalide or by reaction of an α-bromoacetophenone with an N,N'-dibenzyl-polymethylenediamine, with further operations depending on the nature of the 3-substituent, and subsequently hydrogenating catalytically with for example palladium-on-carbon. The key intermediates are also part of the invention.
α-Aminoalkyl-4-hydroxy-3-alkylsulfonylmethylbenzyl alcohols having β-adrenergic stimulant activity
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, (2008/06/13)
α-Aminoalkyl-4-hydroxy-3-alkylsulfonylmethylbenzyl alcohols having β-adrenergic stimulant activity, particularly as selected bronchodilators, are prepared from 4-hydroxyphenones by conversion to a 3-alkylsulfonylmethylphenone, bromination of these phenones and treatment of the resulting α-bromo derivatives with an N-benzyl secondary amine, followed by catalytic hydrogenation to remove the benzyl groups and reduce the ketone moiety.
4-HYDROXY-ALPHA-[(3,4-METHYLENEDIOXYPHENYL)ISOPROPYLAMINOETHYL]-3-(METHYLSULFONYLMETHYL)BENZYL ALCOHOL
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, (2008/06/13)
4-Hydroxy-α-(3,4-methylenedioxyphenyl) isopropylaminomethyl!-3-(methylsulfonylmethyl)ben zyl alcohol having β-adrenergic stimulant activity, particularly as a selective bronchodilator, is prepared from 4-hydroxyacetophenone by conversion to 3-methylsulfonylmethylacetophenone, bromination and conversion of this phenone to the phenylglyoxal and treatment of the resulting glyoxal derivative with 3,4-methylenedioxyphenylisopropylamine followed by simultaneous reduction of the imine and ketone moieties and catalytic hydrogenation to remove the benzyl group.
Adrenergic agents. III. Synthesis and adrenergic activity of some catecholamine analogs bearing a substituted sulfonyl or sulfonylalkyl group in the meta position
Kaiser,Schwartz,Colella,Wardell Jr.
, p. 674 - 683 (2007/10/06)
The m phenolic group of catecholamine β adrenergic agonists may be replaced by various functionalities capable of undergoing H bonding. Considerable latitude in the nature of the OH simulating group is permissible with retention of activity; however, the most extensively studied analogs are ones in which a mobile proton is attached to an O or N atom. In a search for new selective bronchodilators a series of catecholamine analogs bearing a substituted sulfonyl or sulfonylalkyl group in the meta position (i.e., groups in which the mobile H is attached to a C atom) was examined. These compounds were studied for β adrenergic agonist activity in vitro by measuring their ability to relax tracheal smooth muscle and to increase the rate of spontaneously beating right atria of guinea pigs. Adrenergic activity was influenced by the nature of the aklylene bridge between the sulfonyl and aromatic groups, branching of the ethanolamine side chain, stereochemistry, and substitution of the sulfonyl and amino groups. β Adrenergic blockade was noted for some compounds having the sulfonyl attached directly to the ring. Greatest β adrenergic agonist potency and tissue selectivity was observed with a m MeSO2CH2 substituent. One of these compounds, α [[(1,1 dimethylethyl)amino]methyl] 4 hydroxy 3 [(methylsulfonyl)methyl]benzenemethanol hydrochloride (sulfonterol hydrochloride, USAN), was studied more extensively in animals and is presently being examined for bronchodilator activity in man.
