WO2005102320A1 - Medicament pour traiter des infections virales - Google Patents

Medicament pour traiter des infections virales Download PDF

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Publication number
WO2005102320A1
WO2005102320A1 PCT/RU2005/000205 RU2005000205W WO2005102320A1 WO 2005102320 A1 WO2005102320 A1 WO 2005102320A1 RU 2005000205 W RU2005000205 W RU 2005000205W WO 2005102320 A1 WO2005102320 A1 WO 2005102320A1
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Prior art keywords
methyl
dimethylaminomethyl
oxi
carboxy
treatment
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PCT/RU2005/000205
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English (en)
Russian (ru)
Inventor
Robert Georgievich Glushkov
Vladimir Alekseevich Maksimov
Vitaly Afanasievich Martyanov
Ravil Avgatovich Hamitov
Alexandr Mihailovich Shuster
Original Assignee
Zakrytoe Aktsionernoe Obschestvo 'masterklon'
Zakrytoe Aktsionernoe Obschestvo 'masterlek'
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Priority claimed from RU2004111871/15A external-priority patent/RU2256451C1/ru
Priority claimed from RU2004111872/15A external-priority patent/RU2255086C1/ru
Priority claimed from RU2004115096/15A external-priority patent/RU2266742C1/ru
Application filed by Zakrytoe Aktsionernoe Obschestvo 'masterklon', Zakrytoe Aktsionernoe Obschestvo 'masterlek' filed Critical Zakrytoe Aktsionernoe Obschestvo 'masterklon'
Publication of WO2005102320A1 publication Critical patent/WO2005102320A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses

Definitions

  • the invention is related to the field of medicine, and specifically for the search and 5 development of new medicinal products for the treatment of viral infections.
  • Famous large quantities of manufactured products Cyclic, Gamicilli and Ganciclovi are used in the treatment of herpes.
  • Interpreters have found their use in the treatment of herbal diseases.
  • Demantadine and Demantadine are used for the treatment and treatment of the disease, but they are ineffective for the treatment of the already developed disease.
  • Beta SSH ⁇ ⁇ me already ⁇ e ⁇ echislenny ⁇ le ⁇ a ⁇ s ⁇ venny ⁇ s ⁇ eds ⁇ v is ⁇ lzuyu ⁇ sya 2 ⁇ e ⁇ a ⁇ a ⁇ a that are ingibi ⁇ ami vi ⁇ usn ⁇ y ney ⁇ aminidazy - Zanamivi ⁇ and ⁇ sel ⁇ amivi ⁇ , ⁇ ye e ⁇ e ⁇ ivny ⁇ i g ⁇ i ⁇ e ⁇ and beta, ⁇ ichem ⁇ e ⁇ vy - ⁇ l ⁇ for treatment and v ⁇ y - ⁇ a ⁇ for treatment,
  • Invasive infection is an acute viral disease, a clinical disorder that is mildly affected by the inactivation and infection of the body, which prevents the patient from suffering
  • pathogens such as pathogens that contribute to the development of pneumonia, in particular due to the onset of pneumonia.
  • pathogens such as pathogens that contribute to the development of pneumonia, in particular due to the onset of pneumonia.
  • the large number of variants of the virus makes it meaningless to prepare a vaccine for the treatment of diseases. There is no specific treatment available. If the disease is severe, you must use it. 2 human immunoglobulin from a series of adult donors. In case of complications, treatment with the appropriate antibiotics is carried out.
  • Typical pneumonia is a distressing disease recently diagnosed in Asia, Northern Germany, and Europe. The disease is caused by 5 viruses and is characterized by rapid development and high lethality. The first cases were recorded in 2003.
  • Virus infection is the main reason for the development of severe dehydration in the early childhood. After illnesses, an irreversible infection occurs in the second place after AI. Up to 40-60%> cases of diarrhea, requiring socialization and the implementation of unsafe 3 measures. With this, there is a significant number of severe illnesses with lethal outcome, such as in children, and in adults. In Russia, about 1 million large easy-to-use infections and more than a half of it are inactive, and there is no inertia, which is not consumed. This treatment for chronic infection remains an unresolved problem.
  • the injection of injectable drugs has become quite possible, since for the first time, 1-methyl-2-phenylmethyl-3-acid, 4-dimethyl, was obtained. Because the product is 1-methyl-2-phenyl-methyl-3-carboxy-4-dimethylaminomethyl-5-oxy-6-bomide, it is free of charge - it is free of charge - it is free of charge South water. The difference in the indicated salt is that 1-methyl-2-phenyl-thiomethyl-3-carboxy-4-dimethylaminomethyl-5-oxi-6-bromide was not used.
  • the second component of the present invention is new compounds - derivative 1-methyl-2-phenylmethyl-3-acid and 4-dimethyl-acid-free
  • salt selected from the group: hydrate, sulphate, bisulphate, disinfectant, hydrate, mesylate, disulphate, weakness, hepatitis, hematoma, hematoma, hematoma, hematoma, hepatoma, hepatoma, hepatoma, hepatoma, hepatoma, hepatoma, hepatoma, hepatoma, hepatoma, hepatoma, hepatoma, hepatoma, hepatoma, hepatoma, hematoma, hematoma, hematoma, hematoma, hematoma, hematoma, hematoma, hematoma, hematoma, hepatoma, and hematoma.
  • the most preferred salt is 1-methyl-2-phenyl-methyl-3-carbethoxy-4-dimethylaminomethyl-5-oxi-6-bromide mesylate:
  • ⁇ aib ⁇ lee ⁇ ed ⁇ ch ⁇ i ⁇ eln ⁇ is ⁇ lz ⁇ va ⁇ following ⁇ izv ⁇ dnye me ⁇ il-1-2- ⁇ enil ⁇ i ⁇ me ⁇ il-3- ⁇ a ⁇ be ⁇ si-4-dime ⁇ ilamin ⁇ me ⁇ il-5- ⁇ si-6-b ⁇ mind ⁇ la: mezila ⁇ , bezila ⁇ , ⁇ zila ⁇ , sul ⁇ a ⁇ , and bisul ⁇ a ⁇ ⁇ a ⁇ zhe gid ⁇ a ⁇ y and s ⁇ lva ⁇ y u ⁇ azanny ⁇ s ⁇ ley.
  • Another aspect of the present invention is a pharmaceutical preparation for the treatment of viral infections.
  • the pharmaceutical com- pensation can be performed in the form of a solid medicinal form, predominantly in the form of a medicine or capsule, and also in the form of a soft medicine ⁇ ayu ⁇ e ⁇ a ⁇ matsev ⁇ iches ⁇ aya ⁇ m ⁇ zitsiya m ⁇ zhe ⁇ by ⁇ vy ⁇ lnena as ⁇ as ⁇ v ⁇ a for ine ⁇ tsy, ⁇ s ⁇ l ⁇ u ⁇ yad n ⁇ vy ⁇ ⁇ edl ⁇ zhenny ⁇ s ⁇ ley me ⁇ il-1-2- ⁇ enil ⁇ i ⁇ me ⁇ il-3- ⁇ a ⁇ b ⁇ si-4-dime ⁇ ilamin ⁇ me ⁇ il-5- ⁇ si-6-b ⁇ mind ⁇ la ⁇ bladayu ⁇ d ⁇ s ⁇ a ⁇ chn ⁇ y ⁇ as ⁇ v ⁇ im ⁇ s ⁇ yu in v ⁇ de.
  • the product may also include hydrated or salted salt.
  • the host (s) should be acceptable to the extent that they are compatible with
  • the products may optionally contain fillers, binders and t. ⁇ . ⁇ a ⁇ zhe ⁇ e ⁇ a ⁇ a ⁇ y m ⁇ gu ⁇ s ⁇ de ⁇ zha ⁇ target d ⁇ bav ⁇ i, ⁇ a ⁇ e ⁇ ⁇ azan ⁇ in " ⁇ a ⁇ k ⁇ " ⁇ agtasei ⁇ sa ⁇ ⁇ s ⁇ e ⁇ z "(2" ⁇ e ⁇ ⁇ : ⁇ e ⁇ ai ⁇ asei ⁇ sa ⁇ ⁇ gezz; 1994.).
  • Target Supplements Includes
  • compositions may include other conventional additives, for example, flavorful, aromatic and t. ⁇ .
  • the effective dose of the active component depends on whether the compound is used (lower doses) or for the treatment of viral infection. Otherwise, an effective dose may also depend on weight, age, weight, and the presence of concomitant diseases.
  • ⁇ a ⁇ ime ⁇ for ⁇ e ⁇ a ⁇ ii ⁇ avi ⁇ usn ⁇ y in ⁇ e ⁇ tsii ⁇ ed ⁇ ch ⁇ i ⁇ eln ⁇ is ⁇ lz ⁇ va ⁇ mezila ⁇ me ⁇ il-1-2- z ⁇ ⁇ enil ⁇ i ⁇ me ⁇ il-3- ⁇ a ⁇ be ⁇ si-4-dime ⁇ ilamin ⁇ me ⁇ il-5- ⁇ si-6-b ⁇ mind ⁇ la in d ⁇ zi ⁇ v ⁇ e ⁇ 0.01 to 0.05 g d ⁇ de ⁇ ey ⁇ 2 d ⁇ 6 le ⁇ , at the rate of 0.05 to ⁇ Dg for 7 children from 6 to 12 years of age and in delivery from 0.05 to 0.2 g for children over 12 years of age and adulthood 3-4 times a day.
  • 1-methyl-2-phenyldimethyl-3-carboxy-4-dimethylaminomethyl-5-oxy-6-bromide may be used in the form of salt or salvage.
  • a particular case is the use of 1-methyl-2-phenyl-methyl-3-carboxy-4-dimethylaminomethyl-5-oxi-6-carbide hydrochloride hydrate.
  • the invention is illustrated, but is not limited to, by the following methods.
  • EXAMPLE 1 Preparation of 1-methyl-2-phenyl-methyl-3-carboxy-4-dimethylaminomethyl-5-hydroxy-6-bromoindole ( ⁇ ).
  • Example 2 Production of a 1-methyl-2-phenyl-thiomethyl-3-carboxyethoxy-4-dimethylaminomethyl-5-oxy-6-bromoindole hydrochloride ( ⁇ ). 0% solution of 0.955 g (2 mmol) of compound I in 5 ml of warm ethanol added a solution of 0.135 ml (2.0 mmol) of 85%> disinfectant mixed with 1.0 ml of ethanol and a diluted solution of 0.5 ml. The precipitated crystals are filtered and dried in a vacuum above ⁇ 2 0 5 , which results in a yield of 1.05 g (yield - 91%) of compound II, mp. 164-166 ° ⁇ (with 5 decomposition).
  • ⁇ - ⁇ -s ⁇ flower ⁇ ( ⁇ , ppm, ⁇ - ⁇ 6 ): 1.25 ( ⁇ , ⁇ , - ⁇ 2 ⁇ 3 ), 2.52 (s, 6 ⁇ , - ⁇ ( ⁇ 3 ) 2 ), 3.67 (s, ⁇ ,> ⁇ - ⁇ 3 ), 4.18 ( ⁇ ggi, 2 ⁇ , -
  • Example 5 Production of 1-methyl-2-phenyl-methyl-3-carboxy-4-dimethylaminomethyl-5-oxo-6-bromoindole bisulphide ( ⁇ ).
  • ⁇ 1-methyl-2-phenyl-methyl-3-carboxy-4-dimethylaminomethyl-5-oxo-6-bromoindole bisulphide
  • For 1.478 g (3.096 mmol) of the compound I add 3 ml of water and 3 ml of 1 ⁇ ⁇ 2 8 ⁇ , the resulting solution, dilute two of this solution, evaporate the solution, remove the solution, and 10 ⁇ 2 0 5 and is commercially available from ⁇ , ⁇ , which, after drying in a vacuum, yields 1.56 g (yield - 87.6%>) of compound V, ⁇ .pl. 144-145 ° C.
  • ⁇ - ⁇ -s ⁇ flower ⁇ ( ⁇ , ppm, ⁇ - ⁇ 6 ): 5 1.26 ( ⁇ , ⁇ , - ⁇ 2 ⁇ 3 ), 2.77 (s, 6 ⁇ , - ⁇ ( ⁇ 3 ) 2 ), 3.70 (s , ⁇ ,> ⁇ - ⁇ 3 ), 4.21 ( ⁇ occidental, 2 ⁇ , - ⁇ ( ⁇ ) - ⁇ 2 -) 5 4.74 (s, 2 ⁇ , -8- ⁇ ), 4.85 (s, 2 ⁇ , - ⁇ 2 - ⁇ ⁇ ), 7.28-7.40 (m, 5 ⁇ , - ⁇ - ⁇ 6 ⁇ 5 ), 8.02 (s, ⁇ , ⁇ -7).
  • Example 6 Preparation of 1-methyl-2-phenyl-methyl-3-carbethoxy-4-dimethylaminomethyl-5-hydroxy-6-bromoindole (VI).
  • a solution of 0.954 g (2 mmol) of compound I in 8 ml of dioxane is added to a solution of 0.225 g (2.3 mmol) of methanesulfur in 2 ml of dioxane and it is removed for a short time.
  • the precipitated crystals are filtered and dried in a vacuum, which results in a yield of 0.82 g 15 (yield - 87.3%) of compound VI, T.pl. 171-172 ° C (with decomposition).
  • ⁇ - ⁇ -s ⁇ flower ⁇ ( ⁇ , ppm, ⁇ - ⁇ 6 ): 1.25 ( ⁇ , ⁇ , - ⁇ 2 ⁇ 3 ), 2.31 (s, ⁇ , ⁇ - ⁇ ), 2.77 (s, 6 ⁇ , - ⁇ ( ⁇ 3 ) 2 ), 3.69 (s, ⁇ ,> ⁇ - ⁇ 3 ), 4.20 ( ⁇ occidental, 2 ⁇ , - ⁇ ( ⁇ ) - ⁇ 2 -), 4.74 (s, 2 ⁇ , - ⁇ - ⁇ 2 -) , 4.85 (s, 2 ⁇ , -C ⁇ 2 - ⁇ ⁇ ), 7.28-7.40 (m, 5 ⁇ , -8- ⁇ 6 ⁇ 5 ), 0 8.03 (s, W, ⁇ -7).
  • EXAMPLE 7 Preparation of a 1-methyl-2-phenyl-methyl-3-carboxyloxy-4-dimethylaminomethyl-5-oxo-6-bromide methane sulfate (VII). 0.5 g of compound VI (EXAMPLE 6) is removed from 2 ml of water, 5 crystals are dried in the air and 0.35 g of compound VII are obtained, mp: 120 ° C, -120 ° C; -120 ° C ) Found,%: C - 46.71, 46.73; ⁇ - 5.17, 5.11; ⁇ - 4.64, 4.54. C 23 ⁇ 3 ⁇ 2 0 7 8 2 .
  • Example 9 Preparation of 1-methyl-2-phenyldimethyl-3- 15 carboxy-4-dimethylaminomethyl-5-oxy-6-bromoindole (IX).
  • a solution of 0.954 g (2 mmol) of compound I in 10 ml of a solution is added to a solution of 0.585 g (3 mmol) of which a solution of 5% of solution is inhibited.
  • the precipitated sediment is filtered and dried on the air, which produces 20 1.13 g (yield 87>) of compound IX, T.pl. 144-146 ° C (with ⁇ pl.). Found,%>: C- 53.57, 53.64; ⁇ -4.99, 5.04; ⁇ - 4.25, 4.27.
  • Example 10 Production of the 1-methyl-2-phenyl-methyl-3-carboxy-4-dimethylaminomethyl-5-oxi-6-bromoindole citrate ( ⁇ ). ⁇ 0.978 g (2.05 mmol) of compound I in 14 ml of ethanol is suitable for use. It increases 0.493 g (2.35 mmol) of citric acid in 6 ml of ethanol and it is evaporated. It is discharged in a minimum volume of ethanol, planted with ethyl ether, the oil that is released is twice grown 12 with fresh products of the environment, the plant is filtered and after drying in a vacuum, 1.13 g (yield - 85%) of compound X, ⁇ .pl.
  • ⁇ - ⁇ -s ⁇ flower ⁇ ( ⁇ , 5 ppm, ⁇ - ⁇ 6 ): 1.24 ( ⁇ , ⁇ , - ⁇ 2 ⁇ 3 ), 2.48 (s, 6 ⁇ , - ⁇ ( ⁇ 3 ) 2 ), 2.53 (s , ⁇ , - ⁇ ⁇ ( ⁇ ) ⁇ ), 2.57 (s, ⁇ , - ⁇ 2 - ⁇ ( ⁇ ) ⁇ ), 2.62 (s, ⁇ , - ⁇ 2 - ⁇ ( ⁇ ) ⁇ ), 2.66 (s, ⁇ , - ⁇ 2 - ⁇ ( ⁇ ) ⁇ ), 3.67 (rier, ⁇ ,> ⁇ - ⁇ 3 ), 4.16 ( ⁇ occidental, 2 ⁇ , - ⁇ (0) - ⁇ 2 -), 4.39 (s, 2 ⁇ , - ⁇ 2 - ⁇ ⁇ ), 4.67 (s, 2 ⁇ , - ⁇ - ⁇ 2 -), 7.28-7.36 (m, 5 ⁇ , -8- ⁇ 6 ⁇ 5 ), 7.85 (s, ⁇ , ⁇ -7).
  • Example 11 Preparation of 1-methyl-2-phenyl-thiomethyl-3-carboxy-4-dimethylaminomethyl-5-hydroxy-6-bromoindole ( ⁇ ) hemimaleate.
  • a solution of 0.29 g (2.5 mmol) of maleic acid in 8 ml of a warm ethyl acetate a solution of 0.955 g (2 mmol) of a compound I is in the body is electrically inactive.
  • ⁇ - ⁇ -s ⁇ flower ⁇ ( ⁇ , ppm, ⁇ - ⁇ 6 ): 1.26 ( ⁇ , ⁇ , - ⁇ 2 ⁇ 3 ), 2.73 (s, 6 ⁇ , - ⁇ ( ⁇ 3 ) 2 ), 3.69 (s, ⁇ ,> ⁇ - ⁇ 3 ), 4.21 ( ⁇ ggling, 2 ⁇ , - ⁇ (0) - ⁇ 2 -), 4.72 (s, 2 ⁇ , -8-
  • Example 14 The effective action of the user in relation to the child's infection.
  • Table 2 The dynamics of the disappearance of clinical symptoms of an infection in children, depending on the incidence of infection.
  • Table 3 The dynamics of the disappearance of functional disorders of children and of infected children, depending on the outcome of the therapy.
  • Table 4 The dynamics of normalizing the frequency of the chair in a large group, depending on the actual therapy.
  • Table 5 The results of an expert evaluation of the clinical effectiveness of a patient in a group of patients.
  • Example 15 The beneficial effect of arabidol in relation to adenovirus infection, which is related to infection.
  • SIGNIFICANT FOX 17 In 10 out of 40 patients (25%), for example, the condition of the patient, while with the patient was positive and on the adenovirus antigen (see table 7). Moreover, in the group of patients who were ill, treated with a biddle, already on the 3rd day 4 of 6, and on the 7th day - all the patients were sanitized from the adenosis, while the treatment was carried out at the same time On the 5th day, only 1 out of 4 patients had it. Table 7 Sanitary efficacy in a large group of patients and in relation to adenovirus.
  • EXAMPLE 16 Intestinalization of the intestinal tract and treatment of an abdominal infection. Involvement affects the quantitative and qualitative composition of the intestinal microorganism through the normalization of its non-existent. The state of intestinal microbiocenosis in the dynamics of the disease in 20 patients ( ⁇ 10 patients in each group) was studied. Table 8 Indicator Dynamics 1 of the concentration of the intestinal tract in children, depending on the outcome of the therapy.
  • a clean medium was removed from the cell with a cell and was added to a test bottle of 1.0 ml of a different medium containing different varieties. 19 concentra tions of the studied facilities. After 4 hours of incubation, at a temperature of 37.0 ° ⁇ , the nutrient medium was drained and introduced into the feeds of 0.1 ml of the suspension of the VC virus, with an increase of 0.001--0.004, which is better. The contact of the virus with the cells is 5–60 minutes at 37.0 ° ⁇ .
  • infectious dose 5.0 1 ⁇ for use and for direct use.
  • Example 19 The positive effect of arabidol and mesylate in relation to vesicular vesicle, Indiana strain, on the cell culture ( ⁇ - ⁇ 6). Testing of preventive and curative activity. From the sample with 3 days old, the cells were removed from the medium and introduced into the test products of 1.0 ml of the containing medium, which contains different types of samples.
  • SIGNIFICANT FOX P ⁇ IL 26 24 suspensions of vesicular virus and after 60 minutes of incubation after removal of the susceptible suspension were added 1.0 ml of a supporting medium.
  • EXAMPLE 20 Obtaining pharmaceutical preparations for the production of tablet mass. Prepare a mixture of 10 g of compound VII; 4.5 grams of sugar; 0.25 g of methyl cellulose; 0.15 g of calcium; 0.10 g of acid stearic. Received after stirring, the mass is used for testing.
  • EXAMPLE 21 Pharmaceuticals for use in capsules.
  • a mixture consisting of 10 g of compound VIII is prepared; 2.8 grams of sugar; 6.0 g microcrystalline cellulose; 0.9 g of kollidona, 0.2 g of aerosil, 0.2 g of calcium of the stearate. Received after mixing, the mass is used for encapsulation.
  • Example 22 Preparation of pharmaceutical preparations for the preparation of a preparation for injections of 100 ml of sterile water, while stirring, add 1 g of compound IV. The resulting product is filtered. The finished product is amplified and used for internal and internal injections. 26
  • EXAMPLE 23 Obtaining pharmaceutical preparations for the implementation of the benefits.
  • Example 24 Preparation of a pharmaceutical preparation for the preparation of an ointment.
  • a mixture is used containing 2 g of compound VII and a filler consisting of 58 g of petroleum jelly and 40 g of lanolin.
  • Prepare an ointment base by mixing anhydrous lanolin with vaseline medical. The mixture is melted at a temperature of 50-55 ° C, then it is cooled to a temperature of 30-35 ° C. At this temperature, the ointment base is mixed with compound VII, placed in the homogenizer and transferred to the homogenization for 2-3 minutes.

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  • Health & Medical Sciences (AREA)
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  • Organic Chemistry (AREA)
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  • Virology (AREA)
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Abstract

L'invention appartient au domaine de la médecine et concerne de nouveaux médicaments destinés au traitement d'infections virales. On utilise en tant que nouveaux composés des sels de 1-méthyl-2-phénylthyométhyl-3-carboéthoxy-4-diméthylaminométhyl-5-oxy-6-bromoindole, qui possèdent des propriétés antivirales par rapport aux infections par rotavirus ou par coronavirus, notamment par rapport à la pneumonie atypique. L'invention concerne également des compositions pharmaceutiques destinées au traitement d'infections virales sur la base de ces sels et un procédé de traitement ou de prévention destiné aux infections virales.
PCT/RU2005/000205 2004-04-21 2005-04-19 Medicament pour traiter des infections virales WO2005102320A1 (fr)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
RU2004111872 2004-04-21
RU2004111871/15A RU2256451C1 (ru) 2004-04-21 2004-04-21 Лекарственное средство для лечения атипичной пневмонии
RU2004111871 2004-04-21
RU2004111872/15A RU2255086C1 (ru) 2004-04-21 2004-04-21 1-метил-2-фенилтиометил-3-карбэтокси-4-диметиламинометил-5-окси-6- броминдола мезилат, обладающий противовирусной активностью, и фармацевтическая композиция с его использованием
RU2004115096 2004-05-20
RU2004115096/15A RU2266742C1 (ru) 2004-05-20 2004-05-20 Лекарственное средство для лечения ротавирусной инфекции

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Cited By (7)

* Cited by examiner, † Cited by third party
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CN100367957C (zh) * 2005-11-29 2008-02-13 沈阳中海生物技术开发有限公司 阿比朵尔及其盐的静脉给药制剂及制备方法
EP2204173A1 (fr) * 2007-09-14 2010-07-07 Zakrytoe Aktsionernoe Obschestvo "Masterklon" Composition pharmaceutique possédant un effet antidiabétique
CN101564389B (zh) * 2009-06-05 2010-10-27 中国人民解放军军事医学科学院军事兽医研究所 盐酸阿比多尔在制备预防和治疗犬瘟热病毒药物中的用途
CN102260205A (zh) * 2011-09-01 2011-11-30 湖北丽益医药科技有限公司 一种甲磺酸阿比朵尔的合成方法
CN102267936A (zh) * 2011-09-01 2011-12-07 湖北丽益医药科技有限公司 一种甲磺酸阿比朵尔晶型的制备方法
CN106366029A (zh) * 2016-08-19 2017-02-01 江苏吴中医药集团有限公司苏州制药厂 一种一水合甲磺酸阿比多尔晶型c及其制备方法与应用
CN106491598A (zh) * 2016-08-30 2017-03-15 江苏吴中医药集团有限公司苏州制药厂 一种甲磺酸阿比多尔的药物制剂及其制备方法与应用

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SU1685933A1 (ru) * 1974-11-27 1991-10-23 Всесоюзный Научно-Исследовательский Химико-Фармацевтический Институт Им.С.Орджоникидзе Хлоргидрат 1-метил-2-фенилтиометил-3-карбэтокси-4-диметиламинометил-5-окси-6-броминдола, обладающий противовирусным действием, и способ его получени
RU2003156C1 (ru) * 1991-11-15 1993-11-15 Специальное конструкторское бюро Всесоюзного института научной и технической информации Устройство дл определени параметров режима работы электрофотографических цилиндров
RU2008004C1 (ru) * 1986-06-25 1994-02-28 Центр по химии лекарственных средств - ВНИХФИ Средство, обладающее профилактическим и лечебным действием в отношении вируса гриппа типа в

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SU1685933A1 (ru) * 1974-11-27 1991-10-23 Всесоюзный Научно-Исследовательский Химико-Фармацевтический Институт Им.С.Орджоникидзе Хлоргидрат 1-метил-2-фенилтиометил-3-карбэтокси-4-диметиламинометил-5-окси-6-броминдола, обладающий противовирусным действием, и способ его получени
RU2008004C1 (ru) * 1986-06-25 1994-02-28 Центр по химии лекарственных средств - ВНИХФИ Средство, обладающее профилактическим и лечебным действием в отношении вируса гриппа типа в
RU2003156C1 (ru) * 1991-11-15 1993-11-15 Специальное конструкторское бюро Всесоюзного института научной и технической информации Устройство дл определени параметров режима работы электрофотографических цилиндров

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
"Role of lopinavir/ritonavir in the thratment f SARS:initial virological and cinical fundings.", THORAX, vol. 59, no. 3, March 2004 (2004-03-01), pages 252 - 256 *

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CN100367957C (zh) * 2005-11-29 2008-02-13 沈阳中海生物技术开发有限公司 阿比朵尔及其盐的静脉给药制剂及制备方法
EP2204173A1 (fr) * 2007-09-14 2010-07-07 Zakrytoe Aktsionernoe Obschestvo "Masterklon" Composition pharmaceutique possédant un effet antidiabétique
EP2204173A4 (fr) * 2007-09-14 2010-12-29 Zakrytoe Aktsionernoe Obschestvo Masterklon Composition pharmaceutique possédant un effet antidiabétique
US8247407B2 (en) 2007-09-14 2012-08-21 Zakrytoe Artsionernoe Obschestvo “Masterclone” Pharmaceutical composition with anti-diabetic action
CN101801373B (zh) * 2007-09-14 2013-03-27 马斯捷尔克劳内部股份公司 具有抗糖尿病作用的药物组合物
CN101564389B (zh) * 2009-06-05 2010-10-27 中国人民解放军军事医学科学院军事兽医研究所 盐酸阿比多尔在制备预防和治疗犬瘟热病毒药物中的用途
CN102260205A (zh) * 2011-09-01 2011-11-30 湖北丽益医药科技有限公司 一种甲磺酸阿比朵尔的合成方法
CN102267936A (zh) * 2011-09-01 2011-12-07 湖北丽益医药科技有限公司 一种甲磺酸阿比朵尔晶型的制备方法
CN102267936B (zh) * 2011-09-01 2013-09-11 湖北丽益医药科技有限公司 一种甲磺酸阿比朵尔晶型的制备方法
CN106366029A (zh) * 2016-08-19 2017-02-01 江苏吴中医药集团有限公司苏州制药厂 一种一水合甲磺酸阿比多尔晶型c及其制备方法与应用
CN106491598A (zh) * 2016-08-30 2017-03-15 江苏吴中医药集团有限公司苏州制药厂 一种甲磺酸阿比多尔的药物制剂及其制备方法与应用

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