Enantiomers derived from (S)-2-amino-2-(3,4-dichlorobenzyl)-1-propanol, their use and method of preparation
AssigneeInstitute de Recherche Jouveinal
InventorsGilbert Aubard, Jacques Bure, Alain Calvet, Claude J. Gouret, Agnes Grouhel, Jean-Louis Junien
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Abstract
Enantiomers of (S) configuration of formula (I) ##STR1## in which R is H or methyl, with antiallergic and in particular antihistaminic activity, useful as medicinal products.
Claims26
(S)-(+)-N-allyl-2-methylamino-2-(3,4-dichlorobenzyl)-1-propanol hydrochloride.
A method of treating a human suffering from allergic or histamine-mediated diseases which comprises administering an anti-allergic effective amount of an enantiomer of (S) absolute configuration defined according to the Cahn-Ingold-Prelog rule and by formula (I):
- ##STR7## in which R is hydrogen or a methyl radical, or one of its addition salts with non-toxic acids.
A process for preparing (S)-(-)-2-amino-2(3,4-dichlorobenzyl)-1-propanol of formula (II) ##STR8## in which R is hydrogen, which comprises reacting 3,4-dichlorophenylacetone with a potassium cyanide and an ammonium carbonate to obtain (+/-)-5-3,4-dichlorobenzyl)-5-hydantoin;
- forming an addition salt by stereospecific salification of (+/-)-5-3,4-dichlorobenzyl)-5-hydantoin with (R)-(+)-.alpha.-methyl-benzylamine;
- treating the addition salt with acid to obtain (S)-(-)-5-(3,4-dichlorobenzyl)-5-methyl hydantoin in an alkaline aqueous solution to obtain (S)-(-)-2-amino-2-(3,4-dichlorobenzyl)alanine;
- and reducing the (S)-(-)-2-amino-2-(3,4-dichlorobenzyl) alanine with a borane-dimethyl sulfide complex to obtain the compound of formula (II).
Dependencies are inferred from the claim text.