Preparation of phenylalanine derivatives bearing a 1,2,4-triazol

Details Preparation of phenylalanine derivatives bearing a 1,2,4-triazol Preparation of phenylalanine derivatives bearing a 1,2,4-triazol

1994-08-11

1996-10-15

Weimar, Elizabeth C.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

530313, 530345, 530333, 562445, C07D24914

Patent

active

055655742

ABSTRACT:
Methods of making unnatural amino acids are provided which unnatural amino acids can be incorporated into peptides which either inhibit or promote the secretion of gonadotropins by the pituitary gland and inhibit the release of steroids by the gonads. These unnatural amino acids are useful in the synthesis of peptides and have the formula (a): ##STR1## where W is (CH.sub.2).sub.n or ##STR2## n is an integer from 1 to 6; j=1, 2 or 3, and preferably, Y is N--CN, X is NH and R.sub.2 is alkyl, modified alkyl, alkenyl, alkynyl, aryl or methyl pyridyl. Disclosed are peptides that are analogs of the decapeptide GnRH wherein there is at least one residue of an unnatural amino acid in the 3-, 5-, 6- and/or 8-positions.

REFERENCES:
Webb et al., "Diphenyl Cyanocarbonimidate, A Versatile Synthon for the Construction of Heterocyclic Systems", J. Heterocyclic Chem., 19: 1205-1206 (1982).
Davies et al., "Chiral Analysis of the Reaction Stages in the Edman method for sequencing Peptides", J. Chem. Soc. Perkin Trans II, pp. 1723-1727 (1984).
Kruse et al., "Synthesis and Evaluation of Multisubstrate Inhibitors of an Oncogene-Encoded Tyrosine-Specific Protein Kinase. 2", J. Med. Chem., 31, pp. 1768-1772, 1988.

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