Heterocyclic compounds and compositions having nevropharmacologi

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...

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514370, 514365, 514377, 514374, 548233, 548235, 548193, 548203, 548100, A61K 31415, A61K 3142, C07D26332, C07D27724

Patent

active

057475156

DESCRIPTION:

BRIEF SUMMARY
NEW COMPOUNDS

This is a 371 of PCT/SE94/00664 filed Jul. 5, 1994.


FIELD OF THE INVENTION

The present invention relates to novel heterocyclic compounds having therapeutic activity, processes and intermediates for their preparation, pharmaceutical formulations containing said compounds and the medicinal use of said compounds.


BACKGROUND OF THE INVENTION

There exists a large group of acute and chronic neuropsychiatric disorders for which safe and clinically effective treatments are not currently available. This diverse group of disorders encompasses a broad spectrum of initial events which are characterised by the initiation of progressive processes that sooner or later lead to neuronal cell death and dysfunction. Stroke, cerebral ischaemia, trauma or a neurodegenerative disease such as Alzheimer's disease or Parkinson's disease are all commonly occurring conditions that are associated with neurodegeneration of the brain and/or spinal cord.
The ongoing search for potential treatments of neurodegenerative disorders has involved investigation of excitatory amino acid antagonists, inhibitors of lipid peroxidation, calcium channel antagonists, inhibitors of specific pathways of the arachidonic acid cascade, kappa opioid agonists, adenosine agonists, PAF antagonists and diverse other agents. At the present time there is no consensus of the relative importance of the role played by compounds belonging to any of these general classes.
In a paper on the thermal and photochemical isomerisations of isoxazoles, A. Padwa et al (J. Amer. Chem. Soc., 1975, 97, 6484-6491) describe methylphenyl(2-phenyl-5-methyloxazol-4-yl) carbinol: ##STR1##
No pharmacological activity is ascribed to said compound.
In patent application EP 313 984, the bromo derivative: ##STR2## is described as an intermediate for the synthesis of imidazole or triazole based antifungal agents.
In patent application WO 91/08744, 4-hydroxythiazole derivatives are claimed which are 5-lipoxygenase inhibitors. One example of such compounds is: ##STR3## 4-Oxygenated thiazoles are not included within the scope of the present invention.
In patent application EP 351 194 and in J. Med. Chem., 1991 34, 2176-2186, compounds of the general formula: ##STR4## wherein Q is thiazolyl, Ar.sup.1 is aryl of up to 10 carbon atoms, Ar.sup.2 is 6-membered aryl, X is O, S, SO, SO.sub.2 or NH and A is as direct link to X or is (1-6C)alkylene, (3-6C)alkenylene, (3-6C)alkynylene or cyclo(3-6C)alkylene are disclosed as 5-lipoxygenase inhibitors. The substituent Ar.sup.1 -A-X is not included within the scope of R.sup.1 in claim 1 of the present invention.
In patent application EP 390 558, imidazoles of the following general structure: ##STR5## are disclosed as aromatase inhibitors. Such compounds are deleted from the scope of the present invention by a disclaimer in claim 1.
In patent application EP 477 141, compounds of the general formula: ##STR6## wherein Z is a five-membered aza-aromatic ring and X is cyano, carbamoyl or substituted carbamoyl are claimed. Said compounds are aromatase inhibitors. Specific examples are 1-(4-cyanophenyl)-1-(5-thiazolyl)ethene and 1-(4-cyanophenyl)-1-(5-thiazolyl)ethanol. Such substituents X are not included within the scope of the present invention.
In Tetrahedron, 1971, 27, 1211-1219 the compound 1-(1,2-dimethyl-4-imidazolyl)-1-phenylethanol is described. This compound is deleted from the scope of the present invention by a disclaimer in claim 1.


THE PRESENT INVENTION

A primary objective of the present invention is to provide structurally novel heterocyclic compounds which by virtue of their pharmacological profile are expected to be of value in the treatment of acute and chronic neuropsychiatric disorders characterised by progressive processes that sooner or later lead to neuronal cell death and dysfunction. Such disorders include stroke; cerebral ischaemia; dysfunctions resulting from brain and/or spinal trauma; hypoxia and anoxia, such as from drowning, and including perinatal and neonatal hypoxic asphyxial brain damage; multi-infarct de

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