Optical isomers
AssigneeState of Israel, Represented by Prime Minister's Office Israel Institute for Biological Research
InventorsAbraham Fisher, Ishal Karton, Eliahu Heidman, Yona Grunfeld, Aharon Levy
Life of this patent
Estimating the term…
Abstract
The (+)-cis-, (-)-cis-, (+)-trans- and (-)-trans- forms of 2-methylspiro(1,3-oxathiolan-5,3')quinuclidine are prepared by optical resolution of each of the (.+-.)-cis- and (.+-.)-trans-isomers. These compounds find application in treating diseases of the central nervous system in mammals, especially diseases due to a deficiency in the central cholinergic system. Biological tests indicate that the (-)-cis-form, as well as the (.+-.)-cis-isomer, shows particular promise for treating senile dementia of Alzheimer's type.
Claims29
The individual optical isomers selected from the group consisting of (+)-cis-, (-)-cis-, (+)-trans- and (-)-trans-2-methylspiro(1,3oxathiolan-5,3')quinuclidine of the formula (I). ##STR1##
(+)-cis-2-methylspiro(1,3oxathiolan-5,3')quinuclidine, the free base in ethanol having [.alpha]sup.20 about +32.+-.1, and acid addition salts thereof.
(-)-cis-2-methylspiro(1,3-oxathiolan-5,3')quinuclidine, the free base in ethanol having [.alpha]sup.20 about -32.+-.1, and acid addition salts thereof.
(+)-trans-2-methylspiro(1,3-oxathiolan-5,3')quinuclidine, the free base in ethanol having [.alpha]sup.20 about +24.+-.1.2, and acid addition salts thereof.
(-)-trans-2-methylspiro(1,3-oxathiolan-5,3')quinuclidine, the free base in ethanol having [.alpha]sup.20 about -24.+-.1.2, and acid addition salts thereof.
A pharmaceutical composition which comprises at least one member selected from the group consisting of (+)-cis-, (-)-cis-, (+)-trans- and (-)-trans-2methylspiro(1,3-oxathiolan-5,3') quinuclidine, or a pharmaceutically compatible acid addition salt thereof, together with an inert carrier or diluent.
A method of treating diseases of the central nervous system in mammals, which comprises administering to the mammal at least one member selected from the group consisting of (+)-cis-, (-)-cis-, (+)-trans- and (-)-trans-2-methylspiro(1,3-oxathiolan-5,3')quinuclidine, or a pharmaceutically compatible acid addition salt thereof.
A method for treating senile dementia of Alzheimer's type, which comprises administering to a patient the compound (-)-cis-2-methylspiro(1,3-oxathiolan-5,3')quinuclidine, or a pharmaceutically compatible acid addition salt thereof.
Dependencies are inferred from the claim text.