Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1991-11-12
1993-03-30
Springer, David B.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
548502, A61K 31405
Patent
active
051985527
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention is in the field of organic chemistry, and more particularly it relates to a novel compound--ethyl 6-bromo-5-hydroxy-4-dimethylaminomethyl-1-methyl-2-phenylthiomethylindole- 3-carboxylate hydrochloride monohydrate, a process for preparing thereof, and a pharmaceutical preparation containing the same having the antiviral, interferon-inducing and immunomodulatory effects.
BACKGROUND ART
Nowadays, much consideration is given to a search for and a study for of antiviral, interferon-inducing and immunomodulatory agents. A special attention focuses on agents which are capable of modulating, potentiating or inhibiting a body's immune reactions--immunomodulators.
Immunomodulator increase a general body resistance effecting specific immune reactions and nonspecific defensive factors including an endogenous interferon production. They are used for treating diseases in pathogenic mechanisms of which disorders of a body immune status play an important role--primary and secondary immunodeficiency conditions including cancers as well as chronic and relapsing virus infections.
Among a few synthetic chemicals used as immunomodulators the most effective and widely used in the clinical practice is levamisole/(-) 2,3,5,6,-tetrahydro-6-phenylimidazo-/2.1.b/-thiazole hydrochloride/. /A.D. Mashkobsky, Lekarstvennye sredstva, 1987, (Moskva), "Meditsina", v. 2, pp. 169-171/.
Levamisile as an immunomodulator is used in a complex therapy of various diseases associated with immunodeficiency conditions. The use of levamisole for treating severe retroforms of herpes virus infection is disclosed in literature. Levamisole as well as some other immunomodulators stimulates the production of serum interferon in the body. The interferon titers, produces by the action of levamisole are not over 80-160 U/ml in a cell culture; 160-320 U/ml in the mouse blood serum and 40-80 U/ml in the human blood serum.
However, levamisole is highly toxic and may cause various side-effects; a headache, sleep disturbances, olfactory hallicinations (odour changes), allergic skin hypersensitivity, influenza-like and neurologic symptoms.
The most prejudicible side-effect which may take place in the treatment by using levamisole as an immunomodulator is agranulocytosis--the decrease of neutrophile to a value below 25%. Therefore, the blood should be systematically assayed during the treatment with levamisole.
At present, antiviral drug preparations are also known to contain adamantane derivatives as an active principle, for example, remantadine (alfa-methyl-1-adamantanemethylamine hydrochloride)/Mekhanizmy antivirusnogo deistvia proizvodnykh adamantana, 1982, (Riga) "Zinatne", pp. 25-29, 129-141/. These preparations have a side-effect on a central nervous system.
SUMMARY OF THE INVENTION
The compounds according to the invention, a process for preparing thereof, and a pharmaceutical preparation containing the same are novel and they have not been reported.
The invention is based on the problem of providing a novel compound having high antiviral, interferon-inducing and immunomodulatory effects, a low toxicity, no side-effects, and a process for preparing thereof.
This problem is solved by providing a new compound--ethyl 6-bromo-5-hydroxy-4-dimethylaminomethyl-1-methyl-2-phenylthiomethylindole- 3-carboxylate hydrochloride monohydrate according to the invention of the following formula: ##STR2##
The compound according to the invention is a crystalline powder, having a colour from white with tints of green-yellow to light-yellow with green hues; a bitter in taste, odourless. The melting point of the compound is not characteristic. When heated for 3 hours at a temperature ranging from 110.degree. to 120.degree. C., it looses the molecule of H.sub.2 O.
The compound of the invention is poorly soluble in water, methanol, ethanol, non-hydroscopic. The solution containing 1 g of the compound in 1450 ml of water at 25.degree. C. has pH of 4.37 (potentiometrically).
The UV spectrum of a 0.001% solution of the compound of the inventi
REFERENCES:
patent: 4124702 (1978-11-01), Lampson et al.
patent: 4215137 (1980-07-01), Dobson et al.
patent: 4619942 (1986-10-01), Tidwell et al.
Bogdanova Nadezhda S.
Bryantseva Elena A.
Fomina Alla N.
Grinev, deceased Alexei N.
Grineva Galina V.
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