Analogs of neurohypophysial hormones

Details Analogs of neurohypophysial hormones Analogs of neurohypophysial hormones

1983-05-10

1984-11-20

Phillips, Delbert R.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

424177, C07C10352, H61K 3700

Patent

active

044837941

ABSTRACT:
Analogs of neurohypophysial hormones with inhibition properties are described. The hormones are of the formula ##STR1## wherein in all chiral amino acids are of the L-series and the aromatic amino acid in the position 2, indicated with an asterisk, is of the D-series, and where R.sup.1 and R.sup.2 are hydrogen or a methyl group, R.sup.3 is hydrogen, an amino group, or a triglycylamine grouping, R.sup.4 is hydrogen, a methyl, ethyl or ethoxy group, R.sup.5 is S--CH.sub.2 or S--S group, X.sup.1 is a residue of isoleucine or phenylalanine, X.sup.2 is a residue of leucine or lysine, and X.sup.3 is a glycinamide residue or a hydroxyl group.
These compounds exhibit inhibition effects towards the uterotonic and pressor activity of natural hormones. The common structural feature of all these analogues is the presence of an aromatic hydrophobic D-amino acid in the position 2.

REFERENCES:
patent: 3415805 (1968-12-01), Siedel et al.
patent: 3980631 (1976-09-01), Prochazka et al.
patent: 4237119 (1980-12-01), Cort et al.
patent: 4399125 (1983-08-01), Manning et al.
patent: 4402942 (1983-09-01), Melin
Schroder, et al.; The Peptides (1966), pp. 320, 321, 324, 325, 334 & 335.

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