Carbamates of 2-heterocyclic-1,2-ethanediols
Carbamate compounds of 2-heteroaryl-1,2-ethanediol are described. The compounds are effective in the treatment of disorders of the central nervous system, especially as anti-convulsive or anti-epileptic agents.
1. A compound represented by the formula:
wherein A is a heterocyclic moiety selected from those represented by the formulae
optionally substituted by one or more substituents selected from the group consisting of alkyl, aryl, halogen, trihalomethyl, trihalomethoxy, trialkylsilyl, S(O)R, SO 2 R, SO 2 NRR′, SO 3 R, SR, NO 2 , NRR′, OR, CN, C(O)R, OC(O)R, NHC(O)R, CO 2 R and CONRR′, wherein R and R′ are independently hydrogen, alkyl or aryl; B 1 and B 2 are independently hydroxy or OCONR 1 R 2 , provided that B 1 and B 2 are not simultaneously hydroxy,: and R 1 and R 2 are independently selected from the group consisting of hydrogen, hydroxy, alkyl, alkoxy, alkylaryl, arylalkyl, aryl and aryloxy, and each of R 3 , R 4 and R 5 is independently selected from the group consisting of hydrogen, halogen, trihalomethyl, alkyl and aryl, and their enantiomers, enantiomeric mixtures thereof, and pharmaceutically acceptable salts thereof.
2. A compound in accordance with claim 1 , wherein said compound is a pure enantiomer or an enantiomeric mixture wherein one enantiomer predominates.
3. A compound in accordance with claim 1 , wherein B 1 and B 2 are OCONH 2 .
4. A compound in accordance with claim 1 , wherein only one of B 1 and B 2 is OCONH 2 .
5. A compound in accordance with claim 1 , wherein said compound is (±)-(2-(5-chloro-2-thienyl)-2-carbamoyloxyethyl) oxocarboxamide.
6. A compound in accordance with claim 1 , wherein said compound is (±)-(2R)-(2-(5-chloro-2-thienyl)-2-carbamoyloxyethyl) oxocarboxamide.
7. A compound in accordance with claim 1 , wherein said compound is (−)-(2S)-(2-(5-chloro-2-thienyl)-2-carbamoyloxyethyl) oxocarboxamide.
8. A compound in accordance with claim 1 , wherein said compound is (2-(5-trifluoromethyl-2-thienyl)-2-carbamoyloxyethyl) oxocarboxamide.
9. A compound in accordance with claim 1 , wherein said compound is (2-(5-bromo-2-thienyl)-2-carbamoyloxyethyl) oxocarboxamide.
10. A pharmaceutical composition comprising an effective amount of a compound of in accordance with claim 1 for treating disorders of the central nervous system.
11. A pharmaceutical composition in accordance with claim 10 , wherein the central nervous systems disorder being treated is selected from the group consisting of convulsions, epilepsy, stroke, neurogenic pain and muscle spasm.
12. A pharmaceutical composition in accordance with claim 10 , wherein said compound is a pure enantiomer or an enantiomeric mixture wherein one enantiomer predominates.
13. A method for the treatment of a central nervous system disorder which comprises administering to a host requiring such treatment an effective amount of a compound in accordance with claim 1 .
14. A method in accordance with claim 13 , wherein said compound is a pure enantiomer or an enantiomeric mixture wherein one enantiomer predominates.