Novel aspartylamide derivatives and sweeteners

Details Novel aspartylamide derivatives and sweeteners Novel aspartylamide derivatives and sweeteners

C - Chemistry, Metallurgy

07

C

C07C 235/74 (2006.01) A23L 1/236 (2006.01) C07C 237/08 (2006.01) C07C 255/29 (2006.01) C07D 213/56 (2006.01) C07D 307/54 (2006.01) C07D 317/60 (2006.01) C07D 333/24 (2006.01)

Patent

CA 2194948

The invention is concerned with novel aspartylamide derivatives having the general formula: R1-NHC1H(CH2COOH)CONH-C2R2R3-C3H(OH)-R4 (I) wherein R1 represents a hydrogen atom, a saturated or unsaturated linear or cyclic hydrocarbon group having from 1 to 13 carbon atoms or a mixed hydrocarbon group thereof; R2 and R3 each represent a hydrogen atom or a substituent selected from the group consisting of alkyl groups having from 1 to 6 carbon atoms, alkoxyalkyl groups having from 2 to 7 carbon atoms, hydroxyalkyl groups having from 2 to 7 carbon atoms, a phenyl group, a 2-furyl group, a dimethylene group, a trimethylene group, a tetramethylene group and a pentamethylene group; when R1 is a saturated or unsaturated linear or cyclic hydrocarbon group having from 1 to 13 carbon atoms or a mixed hydrocarbon group thereof, R4 represents an alkyl group having from 1 to 12 carbon atoms or a substituent of formula (II) or (III), and when R1 is a hydrogen atom, R4 represents a substituent of formula (III): -(CHR5)n-R6 (II) -(CH2)m C4HR7R8 (III) wherein, in formula (II), R5 represents a hydrogen atom or an alkyl group having from 1 to 4 carbon atoms, R6 represents a 3- to 10-membered cycloalkyl group having a total of 12 or less carbon atoms, a cycloalkenyl group, a cycloalkyl group which is substituted by an alkyl group, a cycloalkenyl group, a bicycloalkyl group, a bicycloalkenyl group, or a tricycloalkenyl group, and n represents 0 or 1; and in formula (III), R7 and R8 each represent a hydrogen atom, a cycloalkyl group having from 3 to 4 carbon atoms, an alkyl group having from 1 to 6 carbon atoms, an alkoxyalkyl group having from 2 to 7 carbon atoms, a phenyl group, a phenyl group having a substituent selected from the group consisting of fluorine, chlorine, bromine and iodine atoms, a hydroxy group, an alkyl group having from 1 to 6 carbon atoms, an alkoxy group having from 2 to 7 carbon atoms, a cyano group, a nitro group, an acetyl group, an amino group and an acetylamino group in the 2-, 3- or 4-position, a phenyl group having a methylenedioxy group, a trimethylene group or a tetramethylene group in the 2- and 3-positions or in the 3- and 4-positions, a 2-, 3- or 4-pyridyl group, a 2- or 3-furyl group, or a 2- or 3-thienyl group, and m represents 0 or 1; and the C1-configuration is (S), and the C2-, C3- and C4-configurations are (R), (S) or (RS); and salts thereof. The compounds of formula (I) are useful as sweeteners which are excellent in terms of sweetness intensity, stability and sweetness properties.

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