Ultrashort acting hypnotic barbiturates

Abstract

The subject invention concerns novel compounds that are useful as ultrashort acting hypnotic barbiturates. Specifically exemplified are derivatives of barbituric and thiobarbituric acids. They are rapidly metabolized by blood and tissue enzymes to form polar metabolites with no hypnotic activity and which are rapidly eliminated.

1. A compound selected from the group consisting of:
 3-methyl-4,6-dioxo-5-phenylhexahydropyrimidine-5-acetic Acid, Adamantanemethyl Esteradamantan-   1   - ylmethyl (   1   - methyl -   4 , 6   - dioxo -   5   - phenyl -   2   - thioxohexahydropyrimidin -   5   - yl ) acetate                     
 3-methyl-4,6-dioxo-5-phenylhexahydropyrimidine-5-acetic Acid, Cyclohexyl Estercyclohexyl  2 -(   1   - methyl -   4 , 6   - dioxo -   5   - phenyl -   2   - thioxohexahydropyrimidin -   5   - yl ) acetate                     
 3-methyl-4,6-dioxo-5-δ 2 -cyclopentylhexahydropyrimidine-5-acetic Acid Adamantanemethyl Esteradamantan-   1   - ylmethyl (   5   - cyclopent -   2   - en -   1   - yl -   1   - methyl -   4 , 6   - dioxo -   2   - thioxohexahydropyrimidin -   5   - yl ) acetate                     
 3-methyl-4,6-dioxo-5-δ 2 -cyclopentylhexahydropyrimidine-5-acetic Acid Cyclohexyl Estercyclohexyl  2 -(   5   -( cyclopent -   2   - enyl )-   1   - methyl -   4 , 6   - dioxo -   2   - thioxohexahydropyrimidin -   5   - yl ) acetate                     
 
       and pharmaceutically acceptable salts thereof. 
     
     
       2. A compound selected from the group consisting of:
 3-methyl-4,6-dioxo-5-phenylhexahydropyrimidine-5-acetic Acid, Neopentyl Esterneopentyl  2 -(   1   - methyl -   4 , 6   - dioxo -   5   - phenyl -   2   - thioxohexahydropyrimidin -   5   - yl ) acetate                     
 3-methyl-4,6-dioxo-5-phenylhexahydropyrimidine-5-acetic Acid Isobutyl Esterisobutyl  2 -(   1   - methyl -   4 , 6   - dioxo -   5   - phenyl -   2   - thioxohexahydropyrimidin -   5   - yl ) acetate                     
 3-methyl-4,6-dioxo-5-δ 2 -cyclopentylhexahydropyrimidine-5-acetic Acid Neopentyl Esterneopentyl  2 -(   5   -( cyclopent -   2   - enyl )-   1   - methyl -   4 , 6   - dioxo -   2   - thioxohexahydropyrimidin -   5   - yl ) acetate                     
 3-methyl-4,6-dioxo-5-δ 2 -cyclopentylhexahydropyrimidine-5-acetic Acid Isobutyl Esterisobutyl  2 -(   5   -( cyclopent -   2   - enyl )-   1   - methyl -   4 , 6   - dioxo -   2   - thioxohexahydropyrimidin -   5   - yl ) acetate                     
 
       and pharmaceutically acceptable salts thereof. 
     
     
       3. A compound selected from the group consisting of:
 4,6-dioxo-5-allyl-5-isopentylhexahydropyrimidine-3-aceticacid, Ethyl Esterethyl  2 -(   5   - allyl -   5   - isopentyl -   4 , 6   - dioxo -   2   - thioxotetrahydropyrimidin -   1   (   2 H )- yl ) acetate                     
 3-ethoxycarbonyl-4,6-dioxo-5-allyl-5-isopentylhexahydropyrimidineethyl  5 - allyl -   5   - isopentyl -   4 , 6   - dioxo -   2   - thioxotetrahydropyrimidine -   1   (   2 H )- carboxylate                     
 
       and pharmaceutically acceptable salts thereof. 
     
     
       4. A composition comprising the compound according to  claim 1  and a pharmaceutically acceptable carrier or diluent. 
     
     
       5. A composition comprising the compound according to  claim 2  and a pharmaceutically acceptable carrier or diluent. 
     
     
       6. A composition comprising the compound according to  claim 3  and a pharmaceutically acceptable carrier or diluent.