Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Peptide containing doai
Patent
1989-02-03
1991-03-26
Lee, Lester L.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Peptide containing doai
530329, C07K 706, A61K 3702
Patent
active
050029339
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention relates to organic chemistry and more particularly it relates to a novel hexapeptide and a novel medicinal preparation to treat erosive and ulcerative lesions of the gastrointestinal tract, based thereon.
2. Prior Art
Antagonists to histamine H.sub.2 receptors, e.g. cimetidine, (Somerville K. M., Langman, M. J. S. "Drugs", 1983, 24, p. 315-330) are now widely used (per os) to treat exacerbations of gastric and duodenal ulcer. Said preparations is given as tablets for several months. Short courses of cimetidine therapy usually provoke relapses of peptic ulcer. Administration of cimetidine produces some side effects, such as diarrhea, myalgia, allergic reactions, depressions, gynaecomasty due to hypersecretion of prolactin, inhibition of the intrinsic factor secretion and of vitamin B.sub.12 absorption, and impairment of the excretory hepatic function. For these consideration cimetidine is not recommended for treatment of patients with hepatic and renal failure and some other diseases.
Patients with ulcerative colitis are now mainly treated with sulfasalazine (a mixture of 5-aminosalicylate and sulfapyridine). It is given orally, but is poorly tolerated by patients, producing side effects such as nausea, vomiting, headache, allergic response and leucopenia ("Inflammatory Bowel Diseases", ed. by R. N. Allan, Edinburg, 1983).
A hexapeptide having the formula Tyr-D-Ala-Gly-Phe-Leu-Arg is known in the prior art. Its structure is similar to that of the proposed new hexapeptide (U.S. Pat. No. 4,565,005), and the preparation is used to treat duodenal ulcer. But the preparation is effective only when given parenterally, while its efficacy with administration per os is low.
SUMMARY OF THE INVENTION
The herein-proposed hexapeptide and a medicinal preparation produced from it are novel and have not been described in the literature.
The object of this invention is to provide a novel hexapeptide and a medicinal preparation produced from this hexapeptide that would have high anti-ulcerative activity without producing side effects.
Said object has been attained due to the fact that, according to the invention, a novel hexapeptide is proposed having the following structure:
The hexapeptide proposed herein is a white powder, readily soluble in distilled water, physiological saline, alcohol; insoluble in ether, ethyl actate, benzene, or hexane; [.alpha]sub.D.sup.20 =+29.8.degree. (1.0 with 1.10% Ac OH); R.sub.f : 0.74 (chloroform:methanol:32 percent acetic acid, 60:45:20), 0.42 (ethyl acetate:pyridine:acetic acid:water, 45:20:6:11), 0.48 (n-butyl alcohol:acetic acid:water, 3:1:1): amino acid assay: alanine, 1.02 (I); glycine, 1.00 (I); glutamic acid, 1.04 (I); leucine, 1.02(I); tyrosine, 0.99 (I); phenylalanine, 1.03 (I); findings of high performance liquid chromatography: the peptide was eluted with one peak at 38.24 percent gradient in 12,16 minutes. The column: 250.times.4.6 mm, Ultresphera ODS 5 m; the mobile phase A: 0.05M KH.sub.2 PO.sub.4, B: CH.sub.3 CN; grad 20.fwdarw.50 percent B per 20 min.; pressure, 1500 psi; flow rate, 1 ml/min; detection at 214 nm.
The proposed hexapeptide is potent against ulcer. The medicinal preparation comprising an active principle and a carrier, comprises the proposed hexapeptide as the active principle.
The proposed medicinal preparation can be used in any form suitable for oral administration, e.g. as powder or tablets that can be taken per os with milk, vegetable oil or lipids (in a dispersed form), or in the form of capsules containing any suitable pharmaceutical fat carrier. Besides, the preparation can be given as an intranasal aerosol or as rectal suppositories.
The proposed preparation preferably contains 5-50 mg of the active principle in a single dose. The proposed preparation in the form of capsules contains preferably the active principle in the quantity of 5-50 mg in one capsule, while olive oil is used as a pharmaceutical carrier.
BEST WAY OF CARRYING THE INVENTION INTO EFFECT
The efficacy of the pro
REFERENCES:
patent: 4457917 (1984-07-01), Schaller
patent: 4565805 (1986-01-01), Smirnov et al.
Allan et al., Inflammatory Bowel Diseases, 1983, pp. 126, 218, 233, 418-422.
Somerville et al., Drugs, Mar. 1983, 25(3), 315-330.
Polonskii et al., Chem. Abstracts., 1986, 107(3): 18082r.
Bespalova Zhanna D.
Korobov Nikolai V.
Ovchinnikov Mikhail V.
Pekelis Boris L.
Polonsky Vladimir M.
Lee Lester L.
Maebius Stephen B.
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