Chemistry: natural resins or derivatives; peptides or proteins; – Peptides of 3 to 100 amino acid residues – 8 to 10 amino acid residues in defined sequence
Patent
1995-04-28
1997-08-12
Tsang, Cecilia J.
Chemistry: natural resins or derivatives; peptides or proteins;
Peptides of 3 to 100 amino acid residues
8 to 10 amino acid residues in defined sequence
530313, C07K 700, C07K 706, A61K 3800
Patent
active
056567278
ABSTRACT:
LHRH analogs and congeners with high water solubility have been synthesized. These new analogs had 0%-100% antiovulatory activity at a 0.5 .mu.g dosage and 0%-80% at 0.25 .mu.g. The ED.sub.50 for histamine release was 30.5 .mu.g/ml->300 .mu.g/ml.
REFERENCES:
patent: 2872484 (1959-02-01), Lecher et al.
patent: 4431635 (1984-02-01), Coy et al.
patent: 4444759 (1984-04-01), Rivier et al.
patent: 4504414 (1985-03-01), Folkers et al.
patent: 4530920 (1985-07-01), Nestor et al.
patent: 4647653 (1987-03-01), Coy
patent: 4652550 (1987-03-01), Rivier et al.
patent: 4801577 (1989-01-01), Nestor, Jr. et al.
patent: 4851385 (1989-07-01), Roeske
patent: 4935491 (1990-06-01), Folkers et al.
patent: 5140009 (1992-08-01), Haviv et al.
patent: 5300492 (1994-04-01), Haviv et al.
Karten, et al., "In Vitro Histamine Release with LHRH Analogs," LHRH and Its Analogs; Contraceptive and Therapeutic Applications, Part 2, eds. Vickery et al., pp. 179-190, 1987, published in England.
Humphries et al., "Inhibitory Analogues of the Luteinizing Hormone-Releasing Hormone Having D-Aromatic Residues in Positions 2 and 6 and Variation in Position 3," Journal of Medicinal Chemistry, 21(1):120-123, 1978, published in USA.
Janecka et al., "Design, Synthesis and Bioassays of Analogs of Argtide by Criteria of Potency and Safety," Medicinal Chemistry Research, 1:306-311, 1991, published in USA.
Ljungqvist et al., "Design, Synthesis and Biological Evaluation of Antagonists of LHRH by Criteria of Potency, Safety and Solubility," Z. Naturforsch, 46b:1231-1236, 1991, published in Europe.
Janecka et al., "Superiority of an Antagonist of the Luteinizing Hormone Releasing Hormone with Emphasis on Arginine in Position 8, Named Argtide," Biochemical and Biophysical Research Communications, 180(1):374-379, 1991, published in USA.
Amoss et al., "Purification, Amino Acid Composition and N-Terminus of the Hypothalamic Luteinizing Hormone Releasing Factor (LRF) of Ovine Origin," Biochemical and Biophysical Research Communications, 44(1):205-210, 1971, published in USA.
Bajusz et al., "New Antagonists of LHRH," Int. J. Peptide Protein Res., 32:425-435, 1988, published in Europe.
Bajusz et al., "Highly Potent Antagonists of Luteinizing Hormone-Releasing Hormone Free of Edematogenic Effects," Proc. Natl. Acad. Sci. USA, 85:1637-1641, 1988, published in USA.
Dutta, Anand S., "Luteinizing Hormone-Releasing Hormone (LHRH) Antagonists," Drugs of the Future, 13(8):761-787, 1988, published in Europe.
Edelstein et al., "Single Dose Long-Term Suppression of Testosterone Secretion by a Gonadotropin-Releasing Hormone Antagonist (Antide) in Male Monkeys," Contraception, 42(2):209-215, 1990, published in USA.
Folkers et al., "Antagonists of the Luteinizing Hormone Releasing Hormone (LHRH) with Emphasis on the TRP.sup.7 of the Salmon and Chicken II LHRH's," Biochemical and Biophysical Research Communications, 123(3):1221-1226, 1984, published in USA.
Folkers et al., "Increased Potency of Antagonists of the Luteinizing Hormone Releasing Hormone Which Have D-3-Pal in Position 6," Biochemical and Biophysical Research Communications, 137(2):709-715, 1986, published in USA.
Freidinger et al., "Bioactive Conformation of Luteinizing Hormone-Releasing Hormone: Evidence from a Conformationally Constrained Analog," Science, 210:656-658, 1980, published in USA.
Freidinger et al., "Protected Lactam-Bridged Dipeptides for Use as Conformational Constraints in Peptides," J. Org. Chem., 47:104-109, 1982, published in USA.
Hahn et al., "Reproductive/Endocrine and Anaphylactoid Peptides of an LHRH-Antagonist, ORF 18260 [Ac-DNAL.sup.1 (2), 4FDPhe.sup.2, D-Trp.sup.3, D-Arg.sup.6 ]-GnRH," Life Sciences, 37:505-514, 1985 published in USA.
Humphries et al., "Presence of Proline in Position 3 for Potent Inhibition of the Activity of the Luteinizing Hormone Releasing Hormone and of Ovulation," Biochemical and Biophysical Research Communications, 72(3):939-944, 1976, published in USA.
Karten and Rivier, "Gonadotropin-Releasing Hormone Analog Design. Structure-Function Studies Toward the Development of Agonists and Antagonists: Rationale and Perspective," Endocrine Reviews, 7(1):44-66, 1986, published in USA.
Leal et al., "Prolonged Duration of Gonadotropin Inhibition by a Third Generation GNRH Antagonist," Journal of Clinical Endocrinology and Metabolism, 67(6):1325-1327, 1988, published in USA.
Leal et al., "Probing Studies on Multiple Dose Effects of Antide (NAL-LYS) GNRH Antagonist in Ovariectomized Monkeys," Contraception, 40(5):623-633, 1989, published in USA.
Lee et al., "Comparative Studies on the Hypotensive Effect of LHRH Antagonists in Anesthetized Rats," Life Sciences, 45:697-702, 1989, published in USA.
Ljungqvist and Folkers, "The Reaction of Pyridinecarboxylic Acids with Dicyclohexylcarbodiimide and p-Nitrophenol," Acta Chemica Scandinavica, B42:408-410, 1988, published in Europe.
Ljungqvist et al., "Design, Synthesis and Bioassays of Antagonists of LHRH Which Have High Antiovulatory Activity and Release Negligible Histamine," Biochemical and Biophysical Research Communications, 148(2):849-856, 1987, published in USA.
Ljungqvist et al., "Antide and Related Antagonists of Luteinizing Hormone Release with Long Action and Oral Activity," Proc. Natl. Acad. Sci. USA, 85:8236-8240, 1988, published in USA.
Ljungqvist et al., "Antagonists of LHRH Superior to Antide; Effective Sequence/Activity Relationships," Tetrahedron, 46(9):3297-3304, 1990, published in Europe.
Morgan et al., "Antagonistic Analogs of Luteinizing Hormone-Releasing Hormone Are Mast Cell Secretagogues," Int. Archs. Allergy appl. Immun., 80:70-75, 1986, published in Europe.
Moroder et al., "Di-tert.-butyldicarbonat-ein vorteilhaftes Reagenz zur Einfuhrung der tert.-Butyloxycarbonyl-Schutzgruppe," Hoppe-Seyler's Z. Physiol. Chem., Bd. 357:S. 1651-1653, 1976, published in Europe.
Phillips et al., "Evaluation of the Anaphylactoid Activity of a New LHRH Antagonist," Life Sciences, 43:883-888, 1988, published in USA.
Rao et al., "Synthesis of 3-(3-pyridyl)- and 3-(3-benzo[b]thienyl)-D-alanine," Int. J. Peptide Protein Res., 29:118-125, 1987, published in Europe.
Rivier et al., "New Effective Gonadotropin Releasing Hormone Antagonists with Minimal Potency for Histamine Release in Vitro," J. Med. Chem., 29:1846-1851, 1986, published in USA.
Schally et al., "Gonadotropin-Releasing Hormone: One Polypeptide Regulates Secretion of Luteinizing and Follicle-Stimulating Hormones," Science, 173:1036-1038, 1971, published in USA.
Schmidt et al., "[Ac-D-NAL(2).sup.1, 4FD-Phe.sup.2, D-Trp.sup.3, D-Arg-.sup.6 ]-LHRH, A Potent Antagonist of LHRH, Produces Transient Edema and Behavioral Changes in Rats," Contraception, 29(3):283-289, 1984, published in USA.
Sundaram et al., "Antagonists of Luteinizing Hormone Releasing Hormone Bind to Rat Mast Cells and Induce Histamine Release," Agents and Actions, 25(3/4):307-313, 1988, published in Europe.
Tjoeng et al., "Vier Synthesewege zu (2-Pyrimidinylamino)-n-alkansauren," Chem. Ber., 108:862-874, 1975, published in Europe.
Benoiton, Leo, "Amino Acids and Peptides," Canadian Journal of Chemistry, 42:2043-2047, 1964, published in Canada.
Prasad et al., "Structure-Activity Relationships in Luteinizing Hormone-Releasing Hormone," Journal of Medicinal Chemistry, 19(4):492-495, 1976, published in USA.
Fife and Przystas, "Divalent Metal Ion Catalysts in the Hydrolysis of Esters of Picolinic Acid. Metal Ion Promoted Hydroxide Ion and Water Catalyzed Reactions," J. Am. Chem. Soc., 107:1041-1047, 1985, published in USA.
Bernardi et al., "An Experimental Approach to Long-Lasting Hypotensive Eledoisin-Like Peptides," J. Pharm. Pharmac., 19:95-101, 1967, published in Europe.
Peterman and Fauchere, "Synthesis of .beta.-Pyrazinyl-L-Alanine (Paa).sup.1) and of Peptide Derivatives," Helvetica Chimica Acta, 66(5):1513-1518, published in Europe.
Folkers et al., "Activities of Antagonists of the Luteinizing Hormone Releasing Hormone with Emphasis on Positions 1, 5 and 6 and on Positions 1, 2 and 3," Z. Naturforsch, B: Chem. Sci., 42(1):101-106, 1987, published in Europe.
Hocart et al., "Effe
Bowers Cyril Y.
Folkers Karl A.
Janecka Anna
Board of Regents , The University of Texas System
Harle Jennifer
The Administrators of the Tulane Educational Fund
Tsang Cecilia J.
LandOfFree
Antagonists of LHRH does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Antagonists of LHRH, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Antagonists of LHRH will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-161390