Analogues of 8-D-homoarginine vasopressin

Details Analogues of 8-D-homoarginine vasopressin Analogues of 8-D-homoarginine vasopressin

1993-08-25

1996-01-23

Warden, Jill

Chemistry: natural resins or derivatives; peptides or proteins;

Peptides of 3 to 100 amino acid residues

6 to 7 amino acid residues in defined sequence

530315, 514 16, A61K 3800, C07K 706, C07K 700

Patent

active

054865964

ABSTRACT:
Analogues of 8-D-homoarginine vasopressin were prepared with the general formula ##STR1## where X is L-O-methyltyrosine, L-p-ethylphenylalanine, D-p-ethylphenylalanine, L-p-methylphenylalanine or D-methylphenylalanine and R is cysteine or .beta.-mercaptopropionic acid. These vasopressin analogues exhibited an increased affinity to uterus receptors for oxytocin, where they acted as ocytocin antagonists. Moreover, the analogues of deamino vasopressin have a significantly reduced antidiuretic activity in comparison with [8-D-arginine]vasopressin.

REFERENCES:
patent: 4551445 (1985-11-01), Manning et al.
patent: 4604378 (1986-08-01), Callahan et al.
patent: 4749782 (1988-06-01), Huffman et al.
patent: 4876243 (1989-10-01), Marshall et al.
Bodanszky et al, "Synthesis and Some Pharmacological Properties of 8-L-Homoarginine-vasopressin and of 1-Deamino-8-L-homoarginine vasopressin", J. of Med. Chem., 17, 781-783, 1974.
Zoral, et al, "Amino Acids and Peptides, LXXI, "Synthesis of 1-Deamino-8-D-.gamma. Aminobutyrine-vasopressin, and 1-Deamino-8-D-Arginine-vasopressin, Collection Czechoslov, Chem. Commun., vol. 32 (1967), 1250-1257.
Zoral, et al., Amino Acids and Peptides. XCVII, Collection Czechoslov. Chem. Commun., vol. 35:1716-1726 (1970).
M. Zaoral et al., "Amino Acids and Peptides. LX. Synthesis of D-DAB.sup.8 -Vasopressin," Collection of Czechoslov. Chem. Commun., vol. 31:310-314 (1966).
M. Zaoral et al., "Amino Acids and Peptides. LIX. Synthesis and Some Biological Properties of L-DAB.sup.8 -Vasopressin," Collection Czechoslov. Chem. Commun., vol. 31:90-97 (1966).
M. Zaoral et al., "Amino Acids and Peptides. LXXI. Synthesis of 1-Deamino-8-D-.gamma.-Aminobutyrine-Vasopressin, 1-Deamino-8-D-Lysine-Vasopressin, and 1-Deamino-8-D-Arginine-Vasopressin," Collection Czechoslov. Chem. Commun., vol. 32:1250-1257 (1967).
Collection Czechoslov. Chem. Commun., vol. 35:1716-1726 (1970).
M. Zaoral et al., "[1-.beta.-Mercaptopropionic Acid, 8-D-Norarginine]-Vasopressin. A Further Analog with High and Specific Antidiuretic Effect," Collection Czechoslov. Chem. Commun., vol. 37:3350-3351 (1972).
M. Zaoral et al., "Preparation of [1-.beta.-Mercaptopropionic Acid, 8-D-Homoarginine]-Vasopressin," Collection Czechoslov. Chem. Commun., vol. 40:905-912 (1975).
M. Zaoral et al., "[1-.beta.-Mercaptopropionic Acid, 8-.alpha.-.gamma.-Diaminobutyric Acid]-Vasopressin and [1.beta.-Mercaptopropionic Acid, 8-D-Ornithine]Vasopressin. Synthesis and Biological Effects," Collection Czechoslov. Chem. Commun., vol. 41:2088-2095 (1976).
R. L. Huguenin et al., "Synthese de l'Orn.sup.8 -vasopressine et de l-Orn.sup.8 -oxytocine," vol. XLVI, Fasciculus v, No. 178-179:1669-1676 (1963).
G. Lindeberg et al., "Synthesis and Properties of 1-Deamino-8-L-homolysine-vasopressin," Journal of Medicinal Chemistry, vol. 15, No. 6:629-631 (1972).
G. Lindeberg et al., "Synthesis and Some Pharmacological Properties of 8-L-Homoarginine-vasopressin and of 1-Deamino-8-L-homoarginine-vasopressin," Journal of Medicinal Chemistry, vol. 17, No. 17:781-783 (1974).
G. Lindeberg et al., "Solid Phase Synthesis and Some Pharmacological Properties of 8-D-Homolysine-Vasopressin and 1-Deamino-8-D-Homolysine-Vasopressin," Int. J. Peptide Protein Res., vol. 7:395-401 (1975).
G. Lindebereg et al., "Solid Phase Synthesis and Some Pharmacological Properties of 8-D-Homoarginine-Vasopressin and 1-Deamino-8-D-Homoarginine-Vasopressin," Int. J. Peptide Protein Res., vol. 8:193-198 (1976).
M. Bodanszky et al., "Synthesis and Hormonal Activities of 8-L-Homolysine-vasopressin," Journal of Medicinal Chemistry, vol. 14, No. 12:1197-1199 (1971).
A. Dimeli et al., "Tryptic Splitting of Vasopressin Analogues Containing Homologues of Lysine or Arginine in Position 8," Collection Czechoslov. Chem. Commun., vol. 44:2451-2454 (1979).
J. Skopkova et al., "Prolonged Antidiuretic Action of Vasopressin Analogues in Relation to Their Primary Structure," Collection Czechoslovak Chem. Commun., vol. 46:1850-1855 (1981).

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