Pharmacologically active peptides

C - Chemistry – Metallurgy – 07 – K

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530/5.1

C07K 14/70 (2006.01)

Patent

CA 1187872

Abstract of the Disclosure Compounds of the formula Image and pharmaceutically acceptable non-toxic acid addition salts thereof, in which R is hydrogen, methyl, or ethyl; A is the residue of a D-amino acid selected from Ala, Abu, Nva, Val, Nle, Leu, Ile, Gly(Al), Gly(Cp), Met, Cys(Me), Met(O), Cys(Me)(O), Ser, Thr, and Hse; R1 is hydrogen, C1-C3 primary alkyl, cyclo- propylmethyl, allyl, or propargyl; X is bromo, iodo, chloro, C1-C3 alkyl, tri- fluoromethyl, or C1-C2 alkoxy; B is the residue of a D- or L-amino acid lacking its carboxyl moiety and selected from Gly, Ala, Abu, Nva, Val, Nle, Leu, Ile, Pgl, Cys(Me), Cys(Me)(O), Cys(Me)(02), Cys(Et), Cys(Et)(O), Cys(Et)(O2), Met, Met(O), Met(02), Eth, Eth(O), Eth(02), Ser(Me), Ser(Et), Hse(Me), and Hse(Et) as well as any of such residues substituted at the amino nitrogen by a C1-C3 primary alkyl; Z is -CH20R2, Image , or Image , in which R2 is hydrogen or C1-C3 alkyl; subject to the proviso that, when R1 is other than hydrogen, B is the residue of an amino acid that lacks substitution at the amino nitrogen; which are useful analgesic agents, are described.

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