Branched amides of L-aspartyl-D-amino acid dipeptides

Details Branched amides of L-aspartyl-D-amino acid dipeptides Branched amides of L-aspartyl-D-amino acid dipeptides

1988-07-13

1989-08-08

Siegel, Alan

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549 88, C07D33336, C07D33348

Patent

active

048554545

ABSTRACT:
Amides of L-aspartyl-D-amino acid dipeptides of the formula ##STR1## and physiologically acceptable cationic and acid addition salts thereof wherein R.sup.a is methyl, ethyl, n-propyl or isopropyl; R is a branched member selected from the group consisting of fenchyl, diisopropylcarbinyl, d-methyl-t-butylcarbinyl, d-ethyl-t-butylcarbinyl, di-t-butylcarbinyl, 2-methylthio-2,4-dimethylpentan-3-yl, ##STR2## where at least one of R.sup.3, R.sup.4, R.sup.5, R.sup.6 is alkyl having from one to four carbon atoms and the remainder are hydrogen or alkyl having from one to four carbon atoms, X is O, S, SO, SO.sub.2, C.dbd.O or CHOH; m is zero or 1-4, n and p are each zero, 1, 2 or 3 where the sum of n+p is not greater than 3 and the sum of the carbon atoms in R.sup.3, R.sup.4, R.sup.5 and R.sup.6 is not greater than six, and when both of R.sup.3 and R.sup.4 or R.sup.5 and R.sup.6 are alkyl they are methyl or ethyl, ##STR3## where one of R.sup.7, R.sup.8, R.sup.9 is alkyl having from one to four carbon atoms and the remainder are hydrogen or alkyl having from one to four carbon atoms and the sum of the carbon atoms in R.sup.7, R.sup.8 and R.sup.9 is not greater than six, m and q are the same or different and each have the values previously defined for m; ##STR4## where each of R.sup.12 and R.sup.13 are methyl or ethyl, or R.sup.12 is hydrogen and R.sup.13 is alkyl having from one to four carbon atoms, Z is O or NH and t is 1 or 2, ##STR5## where w is 1-4, R.sup.14 and R.sup.16 are each alkyl having from one to four carbon atoms, R.sup.15 is H, OH, methyl or ethyl and the sum of the carbon atoms in R.sup.14, R.sup.15 and R.sup.16 is not greater than six and when both of R.sup.14 and R.sup.15 are alkyl they are methyl or ethyl, and ##STR6## where R.sup.17 and R.sup.19 are alkyl having from one to four carbon atoms, R.sup.18 and R.sup.20 are H or alkyl having one to two carbon atoms, A is OH and B is H, OH or CH.sub.3 and taken together A and B are ##STR7## where the sum of the carbon atoms in R.sup.17, R.sup.18, R.sup.19 and R.sup.20 is not greater than six and when both of R.sup.17 and R.sup.18 or R.sup.19 and R.sup.20 are alkyl they are methyl or ethyl; said amides are potent sweetners having advantages over the prior art, edible compositions containing them, methods for their use in edible compositions and novel amine and amide intermediates useful in their production.

REFERENCES:
patent: 3364114 (1968-01-01), Kuna et al.
patent: 4375430 (1983-03-01), Sklavounos
patent: 4454328 (1984-06-01), Brennan et al.
patent: 4465626 (1984-08-01), Sklavounos
Chem. Ber., vol. 113, pp. 104-128 (1980).
Chemical Abstract 51, 5710c (1957) and the abstracted Chem. Ber. 89, 1694-1701 (1956).
Chemical Abstract 61, 13847h (1964) and the abstracted J. Chromatog. 15, 314-323 (1964).
Chemical Abstract 67, 2797x (1967) and the abstracted 23 (5), 2421-2429 (1967).

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