Amino acids useful in making GnRH analogs

Details Amino acids useful in making GnRH analogs Amino acids useful in making GnRH analogs

1993-06-17

1994-10-04

Fan, Jane T.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D24914

Patent

active

053527968

ABSTRACT:
Unnatural amino acids are provided which 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; or the formula (b): ##STR3## where R.sub.11 is H or acyl and W is as defined in (a), and preferably R.sub.11 is H and W is ##STR4## 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:
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).
Rivier et al., "Novel Linear and Cyclic Gonadotropin Releasing Hormone Antagonists:", 26.sup.es Recontres Internationales de Chimie Therapeutique, Jul. 3-5, 1990. Abstract.
Moimas et al., "New Approach to 1-Nitro-2,2-bis[alkyl- or arylamino]ethylenes: A New Synthesis of Ranitidine", Communications, pp. 509-510, May 1985.

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