Novel aspartyl dipeptide amide derivatives and sweeteners

Details Novel aspartyl dipeptide amide derivatives and sweeteners Novel aspartyl dipeptide amide derivatives and sweeteners

C - Chemistry, Metallurgy

07

K

C07K 5/072 (2006.01) A23L 1/236 (2006.01)

Patent

CA 2210083

The invention relates to novel aspartyl dipeptide of formula (I): R1-NHC1H(CH2COOH)CO-X-NH-C2R2R3R4 (I) wherein R1 is a hydrogen atom or a hydrocarbon group having from 1 to 13 carbon atoms; R2 and R3 are each, independently, an alkyl group having from 1 to 3 carbon atoms, or C2, R2 and R3 together form a cycloalkyl group having from 3 to 6 carbon atoms, or R2 is a hydrogen atom and R3 is an alkylthioalkyl group having from 2 to 7 carbon atoms, an alkyl-sulfinylalkyl group having from 2 to 7 carbon atoms, an alkylsulfonylalkyl group having from 2 to 7 carbon atoms or an alkoxycarbonylmethyl group having from 2 to 7 carbon atoms; R4 is a phenyl group; a benzyl group; a cyclohexyl group; a cyclohexylmethyl group; a phenyl group substituted at the 2-, 3- or 4-position with a substituent selected from the group consisting of F, Cl, Br, I, a hydroxyl group, an alkoxy group having from 1 to 6 carbon atoms, a cyano group, a nitro group, an acetyl group, an amino group and an acetylamino group; a phenyl group substituted at the position 2- and 3-positions or in the 3- and 4-positions with a substituent selected from the group consisting of a methylenedioxy group, a trimethylene group and a tetramethylene group, a 2-, 3- or 4-pyridyl group; a 2- or 3-furyl group; or a 2- or 3-thienyl group; X is an .alpha.-amino acid residue selected from the group consisting of D-alanine, D-.alpha.-aminobutyric acid, D-norvaline, D-valine, D-norleucine, D-leucine, D-isoleucine, D-alloisoleucine, D-t-leucine, D-serine, D-O-methylserine, D-threonine, D-O-methylthreonine, D-allothreonine, D-O-methylallothreonine, D-S-methyl-cysteine, D-methionine, D-phenyl-glycine, D-furylglycine and L-furylglycine, or X is a residue of a cyclic or acyclic .alpha.,.alpha.-dialkylamino acid having from 3 to 6 carbon atoms; the configuration at the C1-position is (S); the configuration at the C2-position is (R) or (S) when at least two of R2, R3 and R4 are different; and physiologically acceptable salts thereof.

Nouvel aspartyldipeptide de formule R1-NHC1H(CH2COOH)CO-X-NH-C2R2R3R4 (I), où R1 est un atome d'hydrogène ou un groupe hydrocarboné, possédant de 1 à 13 atomes de carbone; R2 et R3 sont chacun, indépendamment l'un de l'autre, un alkyle possédant de 1 à 3 atomes de carbone, ou C2, R2 et R3 forment ensemble un cycloalkyle de 3 à 6 atomes de carbone, ou R2 est un atome d'hydrogène et R3 est un alkylthioalkyle de 2 à 7 atomes de carbone, un alkylsulfinylalkyle de 2 à 7 atomes de carbone, un alkylsulfonylalkyle de 2 à 7 atomes de carbone, un alcoxycarbonylméthyle de 2 à 7 atomes de carbone; R4 est un groupe phényle, benzyle, cyclohexyle, cyclohexylméthyle, phényle avec substitution en position 2-, 3- ou 4- par un groupe choisi parmi F, Cl, Br, I, un hydroxyle, un alcoxy de 1 à 6 atomes de carbone, un cyano, un nitro, un acétyle, un amino et un acétylamino, un phényle avec substitution en positions 2- et 3- ou en positions 3- et 4- par un groupe choisi parmi un méthylènedioxy, un triméthylène et un tétraméthylène, un 2-, 3- ou 4-pyridyle; un 2- ou 3-furyle, ou un 2- ou 3-thiényle; X est un alpha-amino-acide résiduel, choisi parmi les groupes D-alanine, D-alpha-amino-acide butyrique, D-norvaline, D-valine, D-norleucine, D-leucine, D-isoleucine, D-allo-isoleucine, D-t-leucine, D-sérine, D-O-méthylsérine, D-thréonine, D-O-méthylthréonine, D-allothréonine, D-O-méthylallothréonine, D-S-méthylcystéine, D-méthionine, D-phénylglycine, D-furylglycine et L-furylglycine, ou X est un résidu d'acide alpha,alpha-dialkylamino-acide cyclique ou acyclique de 3 à 6 atomes de carbone; la configuration en position C1 est (S); la configuration en position C2 est (R) ou (S) lorsque au moins deux des radicaux R2, R3 et R4 sont différents; leurs sels acceptables du point de vue physiologique.

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