Chemistry: molecular biology and microbiology – Micro-organism – tissue cell culture or enzyme using process... – Preparing alpha or beta amino acid or substituted amino acid...
Patent
1995-10-30
1997-06-03
Lilling, Herbert J.
Chemistry: molecular biology and microbiology
Micro-organism, tissue cell culture or enzyme using process...
Preparing alpha or beta amino acid or substituted amino acid...
435108, 435227, 435228, 435280, 548496, 548497, C12P 1304, C12P 1322, C12P 4100
Patent
active
056353790
ABSTRACT:
Peptides containing in its amino acid chain a D-2-alkylTryptophan residue wherein the alkyl group has between one and three carbon atoms and having pharmacological activity similar to that of analogous peptides containing natural unsubstituted D-Tryptophan residues in place of the D-2-alkylTryptophan. These new peptides are more resistant to oxidative degradation which usually takes place, for example, in the presence of reactive radicals or during high energy sterilization than unsubstituted Tryptophan containing peptides. Specific peptides include His-D-2-alkyl-Trp-Ala-Trp-D-Phe-Lys-NH.sub.2, Ala-His-D-2-alkyl-Trp-Ala-Trp-D-Phe-Lys-NH.sub.2, Pyro-Glu-His-Trp-Ser-Tyr-D-2-alkyl-Trp-Leu-Arg-Pro-Gly-NH.sub.2, Pyro-Glu-His-Ser-Tyr-D-2-alkyl-Trp-Leu-Arg-Pro-NHCH.sub.2 CH.sub.3, D-Pro-Gln-Gln-D-Trp-Phe-D-Trp-2-alkyl-Trp-Met-NH.sub.2, Arg-D-Trp-N-methyl-Phe-D-2-alkyl-Trp-Leu-Met-NH.sub.2, D-Phe-Cys-Phe-D-2-alkyl-Trp-Lys-Thr-Cys-NHCH(CH.sub.2 OH)CHOHCH.sub.3 and D-Phe-Cys-Tyr-D-2-alkyl-Trp-Lys-Val-Cys-Trp-NH.sub.2.
REFERENCES:
patent: 3316260 (1967-04-01), Shen et al.
patent: 3816254 (1974-06-01), Chibata et al.
patent: 3907638 (1975-09-01), Uzuki et al.
patent: 4256641 (1981-03-01), Batcho et al.
patent: 4481362 (1984-11-01), Nakai et al.
patent: 4497957 (1985-02-01), Nakai et al.
patent: 5057615 (1991-10-01), Kono et al.
patent: 5212069 (1993-05-01), Kula et al.
G. Tolis et al. "Growth Hormone Release in Thalassemic Patients by a New GH-Releasing Peptide Administered Intravenously or Orally". 75th Endocrine Society meeting, Las Vegas, NE, Jun. 9, 1993.
R. Deghenghi et al. "Structure-Activity Studies with Hexarelin and Related GH -Releasing Peptides" 3rd Intl. Pituitary Congress Marina de Rey, CA, Jun. 13-15, 1993.
E. Arvat et al. "GH-Releasing Activity of Hexarelin, A New Wynthetic Hexapeptide, After Intravenous, Subcutaneous, Intranasal and Oral Administration In Man" Giornate Endocrinologiche Pisane, Pisa (Italy) Jun. 28-29, 1993.
L.K. Conley et al, "Biological Potency of Hexarelin (EP23905)" Initial Studies on Oral Activity, presented 1992.
W. B. Wehrenberg et al, "Biological Potency of Hexarelin (EP23905), A New Growth Hormone-Releasing Peptide", presented 1992.
R. Deghenghi et al, "Hexarelin(EP23905)--A Superactive Growth Hormone Releasing Peptide", presented in Milan, Italy, Sep. 1992.
Paithorpe et al., Chemical Abstracts 79:400 (1973).
L.K. Conley et al, "Studies on the Mechanism of Action of Hexarelin and GHRP-6", presented at International Symposium on Growth Hormone II, Basic Clinical Aspects, in Tarpon Springs, Florida, Dec. 2-3, 1992.
B.P. Imbimbo et al, "Growth Hormone Releasing Activity of Hexarelin in Humans: A Dose-Responsive Study", presented at the International Symposium on Growth Hormone II, Basic Clinical Aspects, in Tarpon Springs, Florida, Dec. 3-6, 1992.
Silver et al., "Scleroderma, Fascitis, and Eosinophilia Associated With the Igestion of Tryptophan", The New England Journal of Medicine, 322: No. 13, (Mar. 29, 1990).
Karten et al., "Gonadotropin-Releasing Hormone Analog Design, Structure-Function Studies Toward the Development Agonists and Antagonists: Rationale and Perspective", Endocrine Reviews, 7(1):44-66 (1986).
Yabe et al., "Synthesis and Biological Activity of LH-RH Analogs Substituted by Alkyltryptophans at Postion 3", Chem Pharm. Bull., vol. 27 No. 8, (1979).
S. Majima, "E.W. Biologisches Verfahten der d-Tryptophandarstellans", Hoppe-Seyler's Z. Physiol Chem. 243-250 (1936).
Deghenghi Romano
Lilling Herbert J.
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