Hypolipemiant composition and method using thiazole-5-methanols
AssigneeRoussel Uclaf
InventorsMichel Hardy, Daniel Humbert
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AssigneeRoussel Uclaf
InventorsMichel Hardy, Daniel Humbert
Estimating the term…
Novel thiazole derivatives of the formula ##STR1## wherein R is alkyl of 2 to 12 carbon atoms and R.sub.1 is selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms and acyl of an organic carboxylic acid of 1 to 12 carbon atoms having hypolipemiant activity with a very prolonged vasodilatatory activity and their preparation.
An hypolipemiant composition comprising an hypolipemiantly effective amount of at least one compound of the formula ##STR4## wherein R is alkyl of 2 to 12 carbon atoms and R.sub.1 is selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms and acyl of an organic carboxylic acid of 1 to 12 carbon atoms selected from the group consisting of alkanoic acids, cycloalkylcarboxylic acids, cycloalkylalkanoic acids, benzoic acid, and phenyl alkanoic acids and a pharmaceutical carrier.
A method of inducing hypolipemic activity in warm-blooded animals comprising administering to warm-blooded animals an hypolipemically effective amount of at least one compound of the formula ##STR5## wherein R is alkyl of 2 to 12 carbon atoms and R.sub.1 is selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms and acyl of an organic carboxylic acid of 1 to 12 carbon atoms selected from the group consisting of alkanoic acids, cycloalkylcarboxylic acids, cycloalkylalkanoic acids, benzoic acid, and phenyl alkanoic acids.
Dependencies are inferred from the claim text.
From the US filing history. Foreign family members aren’t listed.
Zubarovskii et al [Chem. Ab., Vol 58 (1963), p. 2,525b] describes the preparation of 2-methyl-thiazole-5-methanol by reaction of ethyl 2-methyl-thiazole-5-carboxylate with lithium aluminum hydride but does not describe any pharmacological properties therefor.
It is an object of the invention to provide the novel thiazole derivatives of formula I and a process for their preparation.
It is another object of the invention to provide novel hypolipemiant and vasodilatatory compositions.
In the following examples there are described several preferred embodiments to illustrate the invention. However, it should be understood that the invention is not intended to be limited to the specific embodiments.
Step a: methyl 2-ethyl-thiazole-5-carboxylate
A solution of diazomethane in methylene chloride was added to a suspension of 10.45 g of 2-ethyl-thiazole-5-carboxylic acid in 30 ml of methylene chloride until efferversence stopped and the methylene chloride was distilled. The oily residue was chromatographed over silica and was eluted with a 1:1 mixture of benzene-ethyl acetate to obtain 11.3 g of methyl 2-ethyl-thiazole-5-carboxylate.
Having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole: thiazoles
Medicines and medical preparations
Term ended 6 Sep 1994 (estimated)
USPTO file history isn’t available for this patent, so only indexed dates are shown.