Thiazoline derivatives

Details Thiazoline derivatives Thiazoline derivatives

1996-12-12

1997-09-30

Gerstl, Robert

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D27756

Patent

active

056727127

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/JP95/01169 filed Jun. 12, 1995.


TECHNICAL FIELD

The present invention relates to novel thiazoline derivatives having an inhibitory action of blood platelet aggregation.


BACKGROUND ART

Blood platelet aggregation is considered to occur by the appearance of the binding site to the fibrinogen on the blood platelet membrane glycoprotein GPIIb/IIIa complex caused by stimulation of various blood platelet aggregation-inducing substances. Accordingly, the compounds having an antagonism to fibrinogen receptors have a possibility to show an inhibitory action of blood platelet aggregation.
Compounds disclosed in WO 94/02472 are thiazoline derivatives having an antagonism of fibrinogen receptors, thereby having an inhibitory action of blood platelet aggregation.
However, the compounds disclosed in WO 94/02472 are lowly water-soluble and have a problem of stability in an aqueous solution. Therefore, when administered in the form of an injection solution, these compounds are insufficient for utility as medicines.
An object of the present invention is to provide compounds having an excellent inhibitory action of blood platelet aggregation and good solubility in water, i.e. compounds practicable as an inhibitor of blood platelet aggregation for intravenous administration.


DISCLOSURE OF THE INVENTION

As a result of extensive researches, the present inventors have found that certain thiazoline derivatives achieve the above-mentioned object, and thereby the present invention has been accomplished.
The present invention is a thiazoline derivative represented by Formula: ##STR2## atoms, a cycloalkoxy group having 3 to 6 carbon atoms or a group represented by the formula: phenyl group), R.sup.2 is an alkyl group having 1 to 14 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms or a phenylalkyl group having 7 to 10 carbon atoms, R.sup.3 is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and n is an integer of 2 to 9! or a pharmaceutically acceptable salt thereof.
In the present invention, the alkyl group as used by itself or as a part of certain group refers to a straight or branched alkyl group, i.e., examples of the alkyl group having 1 to 6 carbon atoms are a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, a pentyl group, an isopentyl group and a hexyl group, and examples of the alkyl group having 1 to 14 carbon atoms are, besides the group given above, a 2-methylhexyl group, a 3-methylhexyl group, a heptyl group, an octyl group, a decyl group and a tetradecyl group. In addition, the cycloalkyl group having 3 to 6 carbon atoms refers to a cyclopropyl group, a cyclobutyl group, a cyclopentyl group and a cyclohexyl group. Examples of the phenylalkyl group having 7 to 10 carbon atoms are a benzyl group, a phenethyl group and a phenylpropyl group.
The pharmaceutically acceptable salt of the compound of Formula (I) refers to, for example, salts with an alkali metal, an alkali earth metal, ammonia, an alkylamine, a mineral acid, a carboxylic acid or a sulfonic acid, and more especially sodium salt, potassium salt, calcium salt, ammonium salt, aluminium salt, triethylammonium salt, hydrochloride, hydrobromide, hydroiodide, sulfate, nitrate, phosphate, monomethylsulfate, acetate, propionate, butyrate, succinate, tartrate, citrate, tannate, malate, caproate, valerate, fumarate, maleate, methanesulfonate, tosylate or trifluoroacetate.
Preferred compounds of the present invention are those wherein R.sup.3 is a hydrogen atom, especially those wherein R.sup.1 is a hydroxyl group and R.sup.3 is a hydrogen atom, and more especially those wherein R.sup.1 is a hydroxyl group, R.sup.3 is a hydrogen atom and R.sup.2 is a methyl group.
The most preferred compounds of the present invention are thyl-3H-thiazoline-5-carboxamide and hyl-3H-thiazoline-5-carboxamide.
The compounds of the present invention can be prepared by the following methods.
For the preparation of the compounds of the present invention, first, a

REFERENCES:
patent: 5478945 (1995-12-01), Sato
patent: 5510478 (1996-04-01), Sabb

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