N-.omega.-substituted hormonogens of vasopressin and its...

Details N-.omega.-substituted hormonogens of vasopressin and its... N-.omega.-substituted hormonogens of vasopressin and its...

C - Chemistry, Metallurgy

07

K

167/205, 530/7.1

C07K 7/16 (2006.01) A61K 38/00 (2006.01)

Patent

CA 1246055

Abstract Novel hormonogen forms of biologically active vaso- pressin and its synthetic analogs having extended half-lives and improved actively are obtained by attaching a side peptide chain containing from 1 to about 3 amino acid residues to the free amino group of an alpha-amino acid residue having a basic side chain. Preferred hormonogens may be represented by the structural formula: (I) Image wherein A is hydrogen, hydroxy or lower alkoxy, especially methoxy, B is the peptide residue of phenylalanine (Phe) or isoleucine (Ile), D is the peptide residue of glutamine (Gln) or valine (Val), Asn represents the peptide residue of aspara- gine, E represents the peptide residue of proline (Pro), 4-thioproline (4-thioPro) or 3,4-dehydroproline (3,4-dehydroPro) FNHX represents an N-substituted peptide residue of L- or D lysine (Lys) or L- or D- ornithine (Orn), X represents a side peptide chain as previously defined, G is disulfide (-S-S-) or thioether (-CH2S- or -SCH2-) and J is the peptide residue of glycine (Gly), L-Alanine (L-Ala) or D-Alanine (D-Ala).

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