Tetrapeptides and pentapeptides, their preparation and compositi

Details Tetrapeptides and pentapeptides, their preparation and compositi Tetrapeptides and pentapeptides, their preparation and compositi

1980-06-27

1988-05-03

Brown, J. R.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Peptide containing doai

514 18, 530330, 530331, A61K 3702, C07K 508, C07K 510

Patent

active

047420480

ABSTRACT:
Tetrapeptides and pentapeptides of the formula: ##STR1## wherein R represents hydrogen or a fatty acid residue, R.sub.1 represents hydroxy, amino, alkoxy of 1 to 4 carbon atoms, optionally substituted by phenyl or nitrophenyl, one of R.sub.2 and R.sub.4 represents hydrogen, carboxy, carbamoyl, alkoxycarbonyl of 2 to 5 carbon atoms, optionally substituted by phenyl or nitrophenyl, or a N-carbonylglycine or N-carbonyl-D-alanine radical optionally esterified by alkyl of 1 to 4 carbon atoms (which is optionally substituted by phenyl or nitrophenyl) and the other symbol represents hydrogen, carboxy, carbamoyl, or alkoxycarbonyl fof 2 to 5 carbon atoms, optionally substituted by phenyl or nitrophenyl, and R.sub.3 represents hydrogen, a fatty acid residue or a glycyl or D-alanyl moiety in which the amine group is optionally substituted by a fatty acid residue, it being understood that R.sub.2 and R.sub.4 cannot simutaneously represent hydrogen, that at least one of R.sub.2, R.sub.3 and R.sub.4 represents a glycyl or D-alanyl moiety, that at least one of R and R.sub.3 represents or contains a fatty acid residue, and that the alanine moiety is in the L form, the glutamic acid moiety or its derivatives are in the D form, the lysine moiety or its derivatives, when one of the symbols R.sub.2 and R.sub.4 represents a hydrogen atom, are in the L form, and the 2,6-diaminopimelic acid moiety or fits derivatives, when R.sub.2 and R.sub.4 represent a carboxy, carbamoyl or alkoxycarbonyl radical, are in the D,D L,L,D,D/L,L (racemic) or D,L (meso) form, and salts thereof possess immunostimulant activity.

REFERENCES:
patent: 4261979 (1981-04-01), Solles et al.
patent: 4311640 (1982-01-01), Kuroda et al.
Rudinger, Peptide Harmones, edited by Parsons, University Park Press, Baltimore, pp. 1-7.
Biochem-and Biophys. Res. Commun. 59, 1974 1317-1325.
Biochemistry vol. 9, No. 4, 1970, 823-831.
Comptes Rendus Hebdomandaires Des Scanies De L'Academic Des Sciences Paris pp. 1320-1304 (1965).
Bulletin De La Societe De Chimie Biologique 1967, 49, No. 11 pp. 1579-1591.
Agricultural and Biological Chemistry 41, (5) 763-768, 1977.
11th Internat'l Congress of Chemotherapy--19th Interscience Conference on Antimicrobial Agents & Chemotherapy (1979).
Life Sciences, vol. 26, pp. 883-888 Jan. 17, 1980.
C. R. Acad. Se. Paris, 1.289 (Sep. 24, 1979) Series D-473.

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