Gnrh analogs

Details Gnrh analogs Gnrh analogs

C - Chemistry, Metallurgy

07

K

C07K 7/06 (2006.01) C07C 279/24 (2006.01) C07C 279/28 (2006.01) C07C 313/30 (2006.01) C07D 213/75 (2006.01) C07D 249/14 (2006.01) C07K 1/06 (2006.01) C07K 7/02 (2006.01) C07K 7/23 (2006.01) A61K 38/00 (2006.01)

Patent

CA 2066184

2066184 9106543 PCTABS00005 Peptides which include unnatural amino acids and which either inhibit or promote the secretion of gonadotropins by the pituitary gland and inhibit the release of steroids by the gonads. Administration of an effective amount of such peptides that are GnRH antagonists prevents ovulation of female mammalian eggs and/or the release of steroids by the gonads. The antagonists may be used to treat steroid-dependent tumors, such as prostatic and mammary tumors. The peptides are analogs of the decapeptide GnRH wherein there is at least one residue of an unnatural amino acid in the 3-position, the 5-position, the 6-position and/or the 8-position. Such unnatural amino acids are useful in the synthesis of peptides and have the formula U*: where n is an integer from 1 to 6; Y is N-CN, N-CONHR9, S, O or CH-NO2; R9 is H, Ac, lower alkyl, aromatic or heterocyclic; X is NH, O, S, M1(CHq)pM2 or M1-(CH2)p'-M2(CH2)p''-M3, where M1 is NR10, O, S or CHR3 wherein R3 is methyl, ethyl, propyl, phenyl, pyridinyl, pyrimidinyl or purinyl; q is 1 or 2; p, p' and p'' are integers between 0 and 6; R10 is H, lower alkyl or the like, and M2 and M3 are M1, COOH, CONH2, COOR3 or CN; R1 is H, alkyl, modified alkyl, alkenyl, alkynyl, aryl or a direct bond to X; R2 is R1, OH, NH2, NHR1, or heterocycle.

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