Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1994-06-24
1997-04-22
Chang, Ceila
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514305, 514340, 546135, 546138, 546210, 5462691, A61K 31445, C07D41312
Patent
active
056229763
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/JP92/01658 filed Dec. 18, 1992.
TECHNICAL FIELD
This invention relates to and pharmaceutically acceptable salts thereof which are useful as a medicament.
DISCLOSURE OF INVENTION
This invention relates to new heterocyclic compounds. More particularly, this invention relates to new oxadiazole derivatives and pharmaceutically acceptable salts thereof which have pharmacological activities, processes for preparation thereof, a pharmaceutical composition comprising the same and a use of the same.
Accordingly, one object of this invention is to provide the new and useful oxadiazole derivatives and pharmaceutically acceptable salts thereof which possess an acetylcholinesterase-inhibitory activity and muscarinic agonist activity.
Another object of this invention is to provide processes for preparation of the oxadiazole derivatives and their salts thereof.
A further object of this invention is to provide a pharmaceutical composition comprising said oxadiazole derivatives or a pharmaceutically acceptable salt thereof.
Still further object of this invention is to provide a use of said oxadiazole derivative or a pharmaceutically acceptable salt thereof as a medicament for prophylactic and therapeutic treatment of disorders in the central nervous system such as amnesia, dementia [e.g. senile dementia of Alzheimer type, vascular dementia etc.], cerebrovascular disease, in human being and animals.
The object oxadiazole derivatives of the present invention are novel and represented by the following general formula (I): substituent(s), aryl which may have suitable substituent(s), ar(lower)alkyl which may have suitable substituent(s), or ar(lower)alkenyl which may have suitable substituent(s), ##STR3## (in which R.sup.4 is hydrogen or lower alkyl), a group of the formula: ##STR4## (in which R.sup.8 is hydroxy or protected hydroxy), ##STR5## A is bond, lower alkylene or lower alkynylene and M is a heterocyclic group containing at least one nitrogen atom which may have one substituent selected from the group consisting of lower alkyl, an imino protective group and ar(lower)alkyl which may have suitable substituent(s).
The object compound (I) of the present invention can be prepared by the following processes. ##STR6## wherein may have suitable substituent(s), substituent(s), or ar(C.sub.1 -C.sub.5)alkyl which may have suitable substituent(s), has an imino protective group, ##STR7## is a saturated heterocyclic group containing at least one nitrogen atom.
The starting compounds can be prepared by the following Processes. ##STR8## wherein ##STR9## are each as defined above, R.sub.a.sup.1 is aryl having lower alkylthio, alkylsulfonyl, has a substituent selected from the group consisting of lower alkyl and ar(lower)alkyl which may have suitable substituent(s), has a substituent selected from the group consisting of (C.sub.1 -C.sub.5)alkanoyl, aroyl which may have suitable substituent(s) and ar(C.sub.1 -C.sub.5)alkanoyl which may have suitable substituent(s), has a substituent selected from the group consisting of lower alkyl and ar(lower)alkyl which may have suitable substituent(s).
Suitable pharmaceutically acceptable salts of the object compound (I) are conventional non-toxic salts and may include a salt with a base or an acid addition salt such as a salt with an inorganic base, for example, an alkali metal salt (e.g. sodium salt, potassium salt, etc.), an alkaline earth metal salt (e.g. calcium salt, magnesium salt, etc.), an ammonium salt; a salt with an organic base, for example, an organic amine salt (e.g. triethylamine salt, pyridine salt, picoline salt, ethanolamine salt, triethanolamine salt, dicyclohexylamine salt, N,N'-dibenzylethylenediamine salt, etc.); an inorganic acid addition salt (e.g. hydrochloride, hydrobromide, sulfate, phosphate, etc.); an organic carboxylic or sulfonic acid addition salt (e.g. formate, acetate, trifluoroacetate, meleate, tartrate, fumarate, methanesulfonate, benzenesulfonate, toluenesulfonate, etc.); a salt with a basic or acidic amino acid (e.g. arginin
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Kuno Atsushi
Ohkubo Mitsuru
Takasugi Hisashi
Chang Ceila
Fujisawa Pharmaceutical Co. Ltd.
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