Carbamate compounds and processes for preparing the same
AssigneeYukong Limited
InventorsYong Moon Choi, Dong Il Han, Kwang Hyouk Lee, Hyung Cheol Kim
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Abstract
(S)-2-Aryl-1,3-propanediol monocarbamate and its intermediate, (S)-3-acetoxy-2-aryl-propanol carbamate, represented by the following formulas I and II, respectively, have pharmaceutically useful activity against for central nervous system disorders including nervous myalgia, epilepsy and cerebral apoplexy: ##STR1## wherein, R is ##STR2## wherein X is an oxygen atom or a sulfur atom; and Y represents a halogen element, trifluoromethyl, or a lower alkyl group containing one to three carbon atoms.
Claims14
(S)-2-Aryl-1,3-propanediol monocarbamate, represented by the following Formula I:
- ##STR7## wherein, R is ##STR8## wherein X is an oxygen atom or a sulfur atom;
- and Y represents a halogen element, trifluoromethyl, or a lower alkyl group containing one to three carbon atoms.
(S)-3-Acetoxy-2-arylpropanol carbamate, represented by the following Formula II:
- ##STR9## wherein, R is ##STR10## wherein X is an oxygen atom or a sulfur atom;
- and Y represents a halogen element, trifluoromethyl, or a lower alkyl group containing one to three carbon atoms.
A process for preparing (S)-3-acetoxy-2-arylpropanol carbamate, represented by the following Formula II:
- ##STR11## wherein, R is ##STR12## wherein X is an oxygen atom or a sulfur atom;
- and Y represents a halogen element, trifluoromethyl, or a lower alkyl group containing one to three carbon atoms, in which (R)-3-acetoxy-2-aryl-propanol, represented by the following Formula III:
- ##STR13## wherein R is as defined above, is reacted with phosgene in the presence of amine base in a solvent mixture of aromatic hydrocarbon and halogenohydrocarbon and then with ammonia, whereby a high optical purity can be obtained within a short time.
A process for preparing (S)-2-aryl-1,3-propanediol monocarbamate, represented by the following Formula I:
- ##STR14## wherein, R is ##STR15## wherein X is an oxygen atom or a sulfur atom;
- and Y represents a halogen element, trifluoromethyl, or a lower alkyl group containing one to three carbon atoms, in which (S)-3-acetoxy-2-aryl-propanol carbamate, represented by the following Formula II:
- ##STR16## wherein R is as defined above, is dissolved in a phosphate buffer solution and added with hydrolase with vigorous stirring, whereby a high optical purity can be obtained within a short time.
Dependencies are inferred from the claim text.