(1-phenyl-1-heterocyclyl)methanol and (1-phenyl-1-heterocyclyl m

Details (1-phenyl-1-heterocyclyl)methanol and (1-phenyl-1-heterocyclyl m (1-phenyl-1-heterocyclyl)methanol and (1-phenyl-1-heterocyclyl m

1995-01-30

1998-01-27

Gerstl, Robert

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

514359, 514374, 548100, 548203, 548235, C07D20330, C07D27730, A61K 3142, A61K 31425

Patent

active

057122997

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/SE94/00665 filed Jul. 5, 1994.
1. 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.
2. 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.
Anticonvulsant agents are widely used, particularly for the treatment of various types of epilepsy. In general, the mechanism of action of such agents is poorly understood and there remains a genuine need for the development of new safe and effective anticonvulsants.
In a paper (J. Org. Chem., 1957, 22, 559-561) on the synthesis of heterocyclic aminoethers related to the antihistamine diphenhydramine, the compounds 1-(4-methyl-5-thiazolyl)-1-phenylmethanol and 1-(2,4-dimethyl-5-oxazolyl)-1-phenylmethanol are described as intermediates.
In J. Org. Chem., 1988, 53, 1748-1761, 1-(5-thiazolyl)-1-phenylmethanol is disclosed.
In J. Org. Chem., 1991, 56, 449-452, 1-(4-oxazolyl)-1-phenylmethanol is described.
In J. Med. Chem., 1984, 27, 1245-1253, 1-(2,4-dimethyl-5-thiazolyl)-1-(2-cholrophenyl) methanol is disclosed as an intermediate in the synthesis of certain heterocyclic analogues of chlorcyclizine with hypolipidemic activity.
No pharmacological activity is ascribed to any of the above confounds. These five compounds are deleted from the scope of the present invention by a disclaimer in claim 1.
In patent application EP 351 194, the compounds; ##STR2## are disclosed. The substituent 2-naphthylmethyloxy is not included within the scope of R.sub.6 of 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 as neuroprotective agents, as anticonvulsant agents and/or as sedative-hypnotics.
Neuroprotective agents are useful 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 ischemia; 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 dementia; AIDS dementia; neurodegenerative diseases such as Alzheimer's disease, Parkinson's disease, Huntington's chorea, epilepsy, multiple sclerosis and amytrophic lateral sclerosis; brain dysfunction in connection with surgery involving extracorporeal circulation or in connection with brain surgery, including endarterectomy of the carotid arteries; and CNS dysfunctions as a result of exposure to neurotoxins or radiation. This utility is manifested, for example, by the ability of these compounds to inhibit delayed neuronal death in the gerbil bilateral occlusion model of ischaemia.
Anticonvulsant agents are useful in the clinic for t

REFERENCES:
Hodges, J. Org. Chem. 56(1) 449 (1991).
Dondeni, J. Org. Chem 53(8) 1748 (1988).
Ashton, J. Med. Chem. 27(10) 1245 (1989).
Craig J. Org. Chem 22 559 (1957).

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