Amino acids and processes for making peptides using same

Details Amino acids and processes for making peptides using same Amino acids and processes for making peptides using same

1995-06-06

1998-01-20

Tsang, Cecilia J.

Chemistry: natural resins or derivatives; peptides or proteins;

Peptides of 3 to 100 amino acid residues

Synthesis of peptides

530334, 530335, 562445, A61K 3800, C07K 200

Patent

active

057102490

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) 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:
patent: 4935491 (1990-06-01), Folkers et al.
patent: 5110904 (1992-05-01), Haviv et al.
patent: 5352796 (1994-10-01), Hoeger et al.
patent: 5565574 (1996-10-01), Hoeger et al.
Theobald et al., "General method for incorporation of modified N.sup..omega. -cyanoguanidino moieties on selected amino functions during solid-phase peptide synthesis," J. Am. Chem. Soc., 112(26):9624-9626 (1990).
Rivier et al., "Gonadotropin releasing hormone antagonists: Novel structures incorporating N.sup..omega. -cyano modified guanidine moieties," Biochem. and Biophys. Research Comm., 176(1):406-412 (1991).
Theobald et al., "Novel Gonadotropin-releasing hormone antagonists: Peptides incorporating modified N.sup..omega. -cyanoguanidino moieties," J. Med. Chem., 34(8):2395-2402 (1991).
Rivier et al., "Gonadotropin-releasing hormone antagonists with N.sup..omega. -triazolylornithine, -lysine, or -p-aminophenylalanine residues at positions 5 and 6," J. Med. Chem., 35(23):4270-4278 (1992).
Rao et al., "Synthesis of cis and trans-4-Aminocyclohexyl-D-Alanine Derivatives and Determination of their Stereochemistry", Organic Preparations and Procedures Int., 23(1), 103-110 (1991). arylamino!ethylenes: A New Synthesis of Ranitidine", Communications, pp. 509-510, May 1985.
Coy et al., Endocrinology, vol. 110, No. 4, pp. 1445-1447 (1982).
Ljungquist et al., Biochemical and Biophysical Research Communications, vol. 148, No. 2 (1987), pp. 849-856.
Nikolics et al., Peptides, vol. 5, pp. 1001-1006 (1984).
Yanagisawa et al., "Histamine H.sub.2 Receptor Antagonists 1. Synthesis of N-Cyano and N-Carbamoyl Amidine Derivatives and Their Biological Activities", J. Med. Chem., 27: 849-857 (1984).
Webb et al., "Diphenyl Cyancarbonimidate and Dichlorodiphenoxymethane as Synthons for the Construction of Heterocyclic Systems of Medicinal Interest", J. Heterocyclic Chem., 24:275-278 (Jan.-Feb. 1987).
Garratt et al., "One-Carbon Compounds as Synthetic Intermediates", J. Org. Chem., 54: 1062-1069 (1989).
Webb et al., "Diphenyl Cyanocarbonimidate, A Versatile Synthon for the Construction of Heterocyclic Systems", J. Heterocyclic Chem., 19: 1205-1206 (1982).
E. Muller, Stuttgart (DE), "Methoden der Organischen Chemie":, vol. 10/1, 4th edition, pp. 545-552 (1970).
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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