Bradykinin antagonist peptides

Details Bradykinin antagonist peptides Bradykinin antagonist peptides

1993-12-16

1995-01-31

Hill, Jr., Robert J.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Peptide containing doai

514 20, 514 2, 514803, 530314, 530328, 930 30, 435107, 548532, A61K 3742, C07K 718

Patent

active

053858891

ABSTRACT:
The substitution of the L-Pro at the 7-position of the peptide hormone bradykinin or other substituted analogs of bradykinin with a D-configuration hydroxyproline ether or thioether converts bradykinin agonists into bradykinin antagonists. The invention further includes the intermediate compounds and additional modifications at other positions within the novel 7-position modified bradykinin antagonists which increase enzyme resistance, antagonist potency, and/or specificity of the new bradykinin antagonists. The analogs produced are useful in treating conditions and diseases of a mammal and human in which an excess of bradykinin or related kinins are produced or injected such as by insect bites.

REFERENCES:
patent: 4242329 (1980-12-01), Claeson et al.
patent: 4483850 (1984-11-01), Patchett et al.
patent: 4693993 (1987-09-01), Stewart et al.
patent: 4801613 (1989-01-01), Stewart et al.
patent: 4822894 (1989-04-01), Geiger et al.
patent: 4923963 (1990-05-01), Stewart et al.
Karanewsky et al., "(Phosphinyloxy) acyl Amino Acid Inhibitors of Angiotensin Converting Enzyme. 2. Terminal Amino Acid Analogues of (S)-1-[6-Amino-2-[[hydroxy(4-phenylbutyl)phosphinyl]oxy]-1-oxohexyl]-L-pro line," Journal of Medicinal Chemistry, vol. 33, No. 5 (1990), pp. 1459-1469.
Smith et al., "Synthesis and Pharmacological Activity of Angiotensin Converting Enzyme Inhibitors: N-(Mercaptoacyl)-4-substituted-(S)-prolines," Journal of Medicinal Chemistry, vol. 31, No. 4 (1988), pp. 875-885.
Krapcho et al., "Angiotensin-Converting Enzyme Inhibitors. Mercaptan, Carboxyalkyl Dipeptide, and Phosphinic Acid Inhibitors Incorporating 4-Substituted Prolines," Journal of Medicinal Chemistry, vol. 31, No. 6 (1988), pp. 1148-1160.
Hock et al., "Hoe 140 A New Potent and Long Acting Bradykinin-Antagonist: in vitro studies", Br. J. Pharmacol., vol. 102, pp. 769-774 (1991).
Wirth et al., "Hoe 140 A New Potent and Long Acting Bradykinin-Antagonist: in vivo studies", Br. J. Pharmacol., vol. 102, pp. 774-777 (1991).
Pongracic et al., "A Competitive Kinin Receptor Antagonist, [DArg.sup.0, Hyp.sup.3, DPhe]-Bradykinin, Does Not Affect the Response to Nasal Provocation With Bradykinin", Br. J. Pharmacol., vol. 31, pp. 287-294 (1991).
Higgins et al., "A Study of the Efficacy of the Bradykinin Antagonist NPC567, in Rhinovirus infections in Human Volunteers", Chemical Abstracts #114: 220805d (1991).
Solder et al., "A Bradykinin Antagonist Modifies Antigen-Induced Airway Hyper-Responsiveness and Airway Inflammation in Allergic Sheep", Am. Rev. Respir. Dis. A327 (1989).
John M. Stewart, "Hydroxyproline Analogs of Bradykinin" Journal of Medicinal Chemistry (1974) vol. 17, No. 5 pp. 537-539.
J. M. Stewart, "Chemistry and Biologic Activity of Peptides Related to Bradykinin" Handbook of Experimental Pharamcol. vol. XXV Supp, Springer-Verlag Berlin Heidelberg N.Y. (1979).
J. Barabe et al. "New Agonist and Antagonist Analogues of Bradykinin", Can. J. Physiol. Pharmacol., vol. 62, 1984 pp. 627-629.
Raymond J. Vavrek, et al., "Smooth Muscle Selectivity in Bradykinin Analogs with Multiple D-Amino Acid Substitutions", Dept. of Biochem., Univ of Colorado School of Medicine, Denver, Colo., pp. 543-547.
J. Rifo et al., "Bradykinin Receptor Antagonists Used To Characterize the Heterogeneity of Bradykinin-induced Responses in Rat vas Deferens" European Journal of Pharmacology, 142 (1987), pp. 305-312.
I. J. Zeitlin et al., "Mobilization of Tissue Kallikrein in Inflammatory Disease of the Colon," Wolfson Labs; Gastrointestinal Unit, West. Gen. Hosp. and Dept. of Clinical Surgery, Univ. of Edinburgh (1972), pp. 133-138.
Kenji Suzuki et al, "Synthesis of Every Kinds of Peptide Fragments of Bradykinin" Chemical Pharm. Bull. (1969) vol. 17, pp. 1671-1678.

Affiliated with

Also associated with

Rating

Bradykinin antagonist peptides does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Bradykinin antagonist peptides, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Bradykinin antagonist peptides will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-1102233