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WO2008150190A1 - Compositions à base de 2,6-di-tret-buthyl-4-méthylphénol et procédé pour soigner des blessures par armes à feu les utilisant - Google Patents

Compositions à base de 2,6-di-tret-buthyl-4-méthylphénol et procédé pour soigner des blessures par armes à feu les utilisant Download PDF

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Publication number
WO2008150190A1
WO2008150190A1 PCT/RU2007/000615 RU2007000615W WO2008150190A1 WO 2008150190 A1 WO2008150190 A1 WO 2008150190A1 RU 2007000615 W RU2007000615 W RU 2007000615W WO 2008150190 A1 WO2008150190 A1 WO 2008150190A1
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WO
WIPO (PCT)
Prior art keywords
wound
wounds
tert
methylphenol
composition
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PCT/RU2007/000615
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English (en)
Russian (ru)
Inventor
Vladislav Nikolaevich Varfolomeev
Gennady Nikolaevich Bogdanov
Alexander Nikolaevich Doronin
Viktor Alexandrovich Mikhailov
Leonid Vasilievich Shevchenko
Alexander Vladimirovich Leshnevsky
Evgeny Arkadievich Shibanov
Original Assignee
Institut Problem Khimicheskoi Fiziki Rossiiskoi Akademii Nauk (Ipkhf Ran)
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from RU2007120435/15A external-priority patent/RU2367418C2/ru
Priority claimed from RU2007120434/15A external-priority patent/RU2367417C2/ru
Priority claimed from RU2007120436/15A external-priority patent/RU2367419C2/ru
Application filed by Institut Problem Khimicheskoi Fiziki Rossiiskoi Akademii Nauk (Ipkhf Ran) filed Critical Institut Problem Khimicheskoi Fiziki Rossiiskoi Akademii Nauk (Ipkhf Ran)
Publication of WO2008150190A1 publication Critical patent/WO2008150190A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
    • A61K31/05—Phenols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K35/00—Medicinal preparations containing materials or reaction products thereof with undetermined constitution
    • A61K35/56—Materials from animals other than mammals
    • A61K35/618—Molluscs, e.g. fresh-water molluscs, oysters, clams, squids, octopus, cuttlefish, snails or slugs
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like

Definitions

  • the invention relates to related fields of medicine and pharmacology, in particular, to the creation of drugs for the accelerated healing of gunshot wounds using compositions developed on a rational basis, as well as to a method for treating gunshot wounds with their use.
  • the free-radical mechanism of the pathogenetic processes of the occurrence and development of secondary tissue damage determines the therapeutic effect in the treatment of gunshot wounds (immediately after injury) with synthetic radical reaction inhibitors (bioantioxidants). Under the influence of these substances that can bind chemically active free radicals formed during gunshot wounds, the development of free-radical processes of membrane pathology and oxidative stress is inhibited.
  • a known method of epithelialization of wounds and ulcers using 5% liniment dibunol [Shaposhnikov Yu. G., Bogdanov G. H., Varfolomeev V. H., Neshev H. I., Maksimova I.A. “Fire wound. Physico-chemical and medical biological aspects, Science, 2002 ”]. This method using dibunol, which prevents the formation and development of secondary necrosis, is the closest analogue of the proposed invention.
  • the drug was used only in the case of long-term non-healing wounds and ulcers, and antioxidants were not used to treat fresh gunshot wounds, although this type of combat injury is characterized by a specific feature.
  • the objective of the invention is the creation of a medicinal product that provides accelerated healing of fresh gunshot wounds, as well as a method for their treatment.
  • the invention relates to the field of field surgery and methods for treating gunshot wounds and proposes to introduce into the composition of the proposed composition for treating fresh gunshot wounds, in addition to an inhibitor of radical reactions, an additional substance that accelerates reparative processes at all stages of the wound healing process. It is proposed to use such compositions to limit the lesion in case of gunshot wounds due to inhibition of the development of secondary necrotic changes in the tissues adjacent to the wound canal and acceleration of reparative processes in the wound and near wound space.
  • the invention relates to a composition for treating gunshot wounds (LEP AH-A) comprising a gel base, and as active components - 2,6-di-tert-butyl-4-methylphenol and carnosine in the following ratio of components, wt.%:
  • the invention relates to a composition for treating gunshot wounds (JlEPAH-B) containing a gel base, and 2,6-di-tert-butyl-4-methylphenol and mollusks as active components in the following ratio, wt.%: 2,6-di-tert-butyl-4-methylphenol 5-10 mollusks 3-5 gel the rest.
  • JlEPAH-B gunshot wounds
  • the invention relates to a composition for the treatment of gunshot wounds (JlEPAH-C), containing a gel base, and 2,6-di-tert-butyl-4-methylphenol, T-activin and thymocide as their active ingredients in the following ratio, wt.%:
  • the invention relates to a method for treating gunshot wounds by applying to a wound an agent containing one of the above compositions (JIEPAH-A, LERAN-B or JIEPAH-C) in an effective amount, the agent being used no later than 12 hours after the wound, followed by 1-2 days after being wounded.
  • an agent containing one of the above compositions JIEPAH-A, LERAN-B or JIEPAH-C
  • composition JlEPAH -A as active components contains 2,6-dieth-butyl-4-methylphenol, which is a synthetic inhibitor of free radical reactions, and the dipeptide is carnosine ( ⁇ -alanylhistidine), which a highly specific inhibitor of lipid peroxidation of muscle tissues and membrane protectors immunomodulator and providing acceleration of reparative processes in the wound and okoloranevom space.
  • 2,6-D-tert-butyl-4-methylphenol is a crystalline powder, white or white with a slightly yellowish tint, practically insoluble in water, easily soluble in alcohol.
  • 2,6-Di-tert-butyl-4-methylphenol is one of the main representatives of the antioxidant group, i.e. compounds which are inhibitors of free radical reactions.
  • a number of studies have shown that various pathological conditions are caused by violations of free radical reactions in membrane lipids, which leads to an intensification of lipid peroxidation.
  • endogenous compounds are formed in the body that inhibit lipid peroxidation (LPO).
  • the second composition of the present invention contains, in addition to 2,6-di-tert-butyl-4-methylphenol, a dietary supplement - mollusks.
  • regulatory peptides are involved in the processes of growth, development, and regeneration.
  • Intensive studies of the role and mechanisms of action of regulatory peptides, conducted in recent years, have led to a radical revision of ideas about the mechanisms of regulation of physiological functions, the principles of coordination of homeostasis processes and the adaptation of functional systems of the body to changing environmental conditions. It is possible that under the influence of peptide preparations, a temporary replacement of the damaged unit of physiological regulation occurs, which makes it possible to restore weakened or lost function in damaged tissues, and then independently maintain it for a long time.
  • Another way of accelerated wound healing is directly related to the activation of the processes of growth and differentiation of tissues in the wound area. From the standpoint of modern biochemistry, this should be coupled with an intensification of the biosynthesis of structural proteins, hormonal and contractile protein macromolecules, and tissue-specific enzymes. For this reason, to ensure the biosynthesis of growth hormone, connective tissue proteins, collagen, elastin, myosin, actin and others, a large number of different amino acids are needed.
  • mollusks classified as food additives.
  • Shellfish is a hydrolyzate of the muscle tissue of marine aquatic organisms of the group of mollusks (scallop, mercenaria, mussel, carbuncle, etc.). It contains mainly all natural L-amino acids in an amount of 60 to 87 wt.%, Including essential aromatic (tyrosine, phenylalanine and histidine) and heterocyclic (proline, histidine) amino acids, as well as acidic (aspartic and glutamine 7-10 mAcc %) and basic (lysine, arginine, 10-25 mass%) amino acids and aminosulfonic acid-taurine.
  • taurine promotes cell proliferation of fibroblasts, acting as a growth modulator.
  • Other sulfur-containing amino acids are represented by cysteine, cystine, and the essential amino acid methionine.
  • the mollusk contains biologically active di- and oligopeptides that are involved in protein metabolism and have a stimulating effect on the processes of growth and differentiation.
  • Shellfish is a commercially available drug. Shellfish and a method for its production are disclosed in RU patent Mi-2171066.
  • composition LERAN-C as active components contains 2,6-di-tert-butyl-4-methylphenol, and two additional biologically active components - T-activin and tomicide.
  • T-activin is a preparation of a polypeptide nature, derived from the thymus gland of cattle. Amorphous white powder, easily soluble in water. It is an immunomodulatory agent. In immunocompromised states, it normalizes the qualitative and functional indicators of the T-system of immunity, stimulates the production of lymphokines, including interferons, and normalizes other indicators of cellular immunity. It is a pharmacopeia drug manufactured by Biomed CJSC.
  • Tomicide is a filtrate of streptococcus culture fluid. It has bactericidal and wound healing properties. Assign for external use in the treatment of purulent wounds, trophic ulcers, pyoderma. It is a pharmacopeia drug manufactured by Biomed CJSC.
  • the gel Used as the basis of the proposed compositions for the treatment of gunshot wounds, the gel is a carrier of effective medicinal components, providing convenient delivery of the claimed components to the place of their direct action.
  • the concept of gel is known and uniquely defined for specialists in the field of pharmaceuticals and medicine.
  • the gel must meet certain requirements, namely: to ensure the dissolution of the active components and their homogeneous distribution throughout the volume, to ensure a shelf life of 2 years in the temperature range of 0-50 ° C, in connection with which a stabilizer (for example, nipagin) is added to it, fragrance (nipazole), gelling agents (glycerin, vegetable oil, hydroxyethyl cellulose), etc. are added to give a pleasant smell.
  • a stabilizer for example, nipagin
  • fragrance nipazole
  • gelling agents glycerin, vegetable oil, hydroxyethyl cellulose
  • a gel of the following composition can be used, g: Hydroxyethyl cellulose,
  • compositions of the invention are prepared by adding the active ingredients to the gel and mixing until a homogeneous mass is obtained.
  • the claimed gel-based compositions can be used as a local dressing for wounds.
  • the dosage of the product depends on the nature and size of the gunshot wound.
  • the gel When the wound is open and there is access to its entire surface, the gel is applied so that the wound is completely covered by the composition.
  • the gel In the case when the inlet and outlet openings of the wound are small in size and access to the wound is limited, the gel is injected with a syringe from a convenient side until traces of gel appear on the opposite side of the wound. This ensures complete coverage of the wound surface.
  • compositions of the studied drugs to accelerate the healing process of gunshot wounds has been demonstrated in experiments on rats, rabbits and pigs.
  • Examples 1A-ZA illustrate the use of the JTEPAH-A composition for treating wounds
  • examples 1B-ZB show the composition JIEPAH-B
  • examples 1C-2C show the composition LERAN-C.
  • Example IA The experiments were carried out on 30 outbred rats weighing 250-300 g, a gunshot wound to which was applied to the muscle tissue of the right thigh with 5.62 caliber ammunition with a bullet speed of 320 m / s.
  • the total assessment of the effect of the studied drug on the course of the wound process is the healing time of gunshot skin and muscle wounds.
  • the use of the composition JIEPAH-A reduces the average healing time of wounds. If in the control the average duration of wound healing was 33.0 + 1.2 days, then in the experimental group it was 18.5 + 1.0 days.
  • Table 1 presents the corrective effect of the composition JIEPAH-A on the course of the wound process of a gunshot wound in the thigh of rats.
  • the data in table 1 indicate the pronounced effect of the applied composition JIEPAH-A on the course of the wound process and wound healing.
  • composition JIEPAH-A reduces inflammatory, dystrophic and microcirculatory changes, which, in turn, weakens the secondary necrotization of muscle tissue and accelerates the filling of the wound canal with maturing granulation tissue.
  • Example 2A In the experiments, 15 Chinchilla rabbits weighing 2.5-3.0 kg were used, gunshot wounds of the soft tissues of the hind limb were inflicted with 5.62 caliber ammunition with a bullet speed of 320 m / s.
  • the size of the inlet is 0.5 x 0.5 cm, the outlet is 1x1 cm, the area of secondary necrosis is 6 cm 2 , the area of secondary necrosis is 24 cm 2 , wounds are purulent, hemorrhages in the subcutaneous tissue are observed.
  • the inlet is 0.3 x 0.3 cm in size
  • the outlet is 0.8 x 0.9 cm
  • the necrotic masses are dense and line the wound canal to a depth of 0.5 cm
  • the size of the secondary necrosis is 3 cm 2
  • the inlet is closed, there is no secondary necrosis, the size of the outlet is 0.5 x 0.7 cm, secondary necrosis extends to a distance not exceeding 0.5 cm from the edge of the wound, hemorrhages and suppuration of wounds are not observed.
  • pigs weighing 50 ⁇ 5 kg were used.
  • the wounds resulting from the munition used are characterized by a funnel shape, i.e. damage intensifies with an increase in the length of the wound channel.
  • traces of an incompletely overgrown wound canal are still visible.
  • the wound channel is not detected, and the wound surface only slightly deepens into the wound.
  • the wound surface is represented by a thin film having a thickness of about 1 mm.
  • This film is quite loose and can easily be separated from the underlying viable tissues, which, when cut, contract and bleed.
  • the experimental testing of the proposed composition JlEPAH-A for the treatment of gunshot wounds showed a significant acceleration of the repair of damaged soft tissues by one third compared with the control.
  • the use of the JIEPAH-A composition prevented the development of purulent complications, as well as reduced the repair time of scar maturation.
  • the antioxidant component of the composition JlEPAH-A (2,6-di-tert-butyl-4-methylphenol) inhibits the free radical reactions of membrane pathology at the molecular level, preventing the development of secondary necrosis in the area of molecular concussion created by firearms wounds.
  • the immunomodulatory component increases local cellular immunity in the areas of a soft soft tissue wound, and also stimulates biosynthetic intracellular processes and endogenous growth factors, which helps to eliminate microbial contamination with a decrease in the risk of purulent complications and accelerate the healing of a wound defect.
  • the proposed method for the treatment of gunshot wounds allows, due to the combined action of the components included in the proposed composition JIEPAH-A, to significantly slow down the secondary damage processes adjacent to the wound canal tissue, significantly limit the degree of surgical intervention, accelerate reparative processes at all stages of the development of the wound process and Thus, to reduce the healing time of the wound, and therefore the rehabilitation of the wounded.
  • Example IB In experiments on rabbits, gunshot wounds were inflicted with 5.45 caliber ammunition and a speed of 600 m / s. On the 5th day after a gunshot wound in animals of the control group, the size of the inlet is 0.5 x 0.5 cm, of the outlet - 1x1 cm. The area of secondary necrosis at the inlet is much smaller than that of output and are 6 cm 2 and 24 cm 2 , respectively. Purulent wounds with hemorrhages in the subcutaneous tissue.
  • the inlet With topical application of the composition JlEPAH-B, the inlet is closed by this time, there is no secondary necrosis.
  • the dimensions of the outlet are 0.5 x 0.7 cm, secondary necrosis is fixed at a distance not exceeding 0.5 cm from the edge of the wound, hemorrhages and suppuration of wounds are not observed.
  • the zone of secondary necrosis from the side of the inlet extends to a distance of 2 cm from the edge of the wound.
  • the outlet in 70% of the animals has a diameter of up to 0.8 cm, in the rest - 0.45 cm, the area of secondary necrosis is 4 cm 2 , extensive hemorrhages and suppuration were noted in all wounds.
  • Example 2B In experiments on pigs weighing 50 ⁇ 5 kg, gunshot wounds were inflicted on the thigh with 5.45 caliber ammunition and a speed of 800 m / s. One hour after the wound, 2,6-di-tert-butyl-4-methylphenol was injected into the wound basis (control group of animals) or composition JIEPAH-B (experimental group).
  • the resulting wounds are characterized by a funnel shape, i.e. damage intensifies with an increase in the length of the wound channel.
  • the wound surfaces of gunshot wounds of soft tissues of pigs on the 5th day after the wound are as follows. Planetrically determined sizes of the area of wounds in the control group of animals (without the use of drugs) are on average 180 cm 2 .
  • the introduction into the wound of the composition JIEPAH-B immediately after a gunshot wound after 5 days leads to a decrease in the area of wounds to 25 cm 2 .
  • the area of the wound outlet in the experimental group is more than 20 times larger than that in the animals of the control group, they observe the filling of the wound canal with mature granulation tissue, while in animals of the control group in section the wound channel made by fibrous dense films is clearly visible. This fact clearly indicates a significant acceleration of wound healing with using the proposed composition.
  • the growth-stimulating and immunomodulating component of the composition activates local cellular immunity in the areas of a soft soft tissue wound and stimulates biosynthetic intracellular processes and endogenous growth factors, which helps to eliminate microbial contamination with a reduced risk of purulent complications and accelerate wound healing.
  • Leran-B composition leads to stimulation of periosteum repair and osteogenesis of damaged bone at an early stage of treatment.
  • a complete demarcation of purulent-necrotic masses from healthy tissues with a dense connective wall is noted.
  • antioxidants Although the effect of antioxidants on a gunshot wound is manifested quite diverse, their main property should be the ability to suppress free radical processes and inhibit the development of secondary necrosis.
  • Example 1C In experiments on rabbits, the wound healing effect of the compositions was studied:
  • the condition of the edges of the wound was determined visually by the intensity of edema, infiltration, hyperemia, epithelization.
  • the condition of the wound walls was determined visually by the presence of fibrin, foci of necrosis and soft tissue fusion.
  • the nature of the wound discharge was assessed visually by color, transparency, consistency, the presence of pus, necrotic detritus, blood impurities, and the presence of odor, given the dominant importance of a particular sign.
  • the development of granulation tissue was studied taking into account the timing of appearance, developmental intensity, color, texture, gloss.
  • the inlet is 5x7 mm
  • the outlet is 15x20 mm
  • the zone of secondary necrosis extends up to 15 mm from the edge of the wound
  • the boundaries of the zones are fuzzy, mosaic in nature
  • extensive hemorrhages in the muscle tissue are observed at a considerable distance from the wound channel.
  • the wound is moderately swollen, with pronounced infiltration especially in the area of the outlet.
  • a significant amount of purulent discharge is characteristic.
  • a completely preserved wound canal made by necrotic tissues, is visible; a region of non-viable tissues of considerable size is visible.
  • the mass of removed non-viable tissue is 8 ⁇ 4g. Healing of such wounds occurs on the 16-18th day after the wound.
  • the inlet In experimental groups of animals, the inlet is usually overgrown, and the size of the outlet is from 5 to 8 mm. The zone of secondary necrosis is practically absent. Hemorrhages are either absent or extend to a distance of 2-3 mm from the edge of the wound only into the subcutaneous tissue without penetration into the muscle mass. Detachable wounds are serous in nature. There is marginal epithelization, the presence of mature granulation tissue is noted. When the wound is dissected, an almost overgrown wound canal is visible, purulent discharge is absent, there are viable muscle tissues around the wound canal, which, when cut, contract and bleed. Wounds heal 10-11 days after the injury.
  • Example 2C For wounds with bullets at a speed of 385 m / s, more severe injuries are observed.
  • the animals of the control group are characterized by large inlet and outlet openings of 8x12 mm and 28x32 mm, respectively.
  • the size of the zone of secondary necrosis reaches 20-25 mm from the edge of the wound, the boundaries of the zones are fuzzy, massive hemorrhages in the muscles and intramuscular fascia.
  • Wounds are characterized by the presence of wound escudate and a significant amount of necrotic tissue and purulent discharge.
  • the mass of removed non-viable tissues is 17 ⁇ 5 g. Healing of such wounds, apparently, is impossible without primary surgical treatment and if it could have happened, then very late. Before animals do not survive the moment, because mortality in this group of animals amounted to more than 70% from 3 to 12 days.
  • the inlet and outlet openings are 4x5 and 6x7 mm, respectively.
  • the sizes of zones of secondary necrosis do not exceed 4 mm from the edge of the wound.
  • Hemorrhages are minor and spread mainly into the subcutaneous tissue.
  • the amount of purulent discharge is negligible.
  • the mass of removed non-viable tissues is 3 ⁇ 1 g. Wound healing is observed on the 16-18th day after the wound.
  • the use of the topically applied composition of JlEPAH-C leads to the healing of gunshot wounds of soft tissues without initial surgical treatment and without the use of antibacterial drugs.
  • this local dressing composition JIEPAH-C in its effectiveness is similar to the action of the composition JIEPAH-B.
  • the proposed method for the treatment of gunshot wounds using the claimed compositions JIEPAH-A, JIEPAH-B and JIEPAH-C can significantly slow down the processes of secondary lesion adjacent to the wound canal tissue, significantly limit the degree of surgical intervention, significantly reduce the size of the lesion, accelerate reparative processes at all stages of the development of the wound process and, thus, reduce the time of wound healing, and therefore the rehabilitation of the wounded.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
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  • General Health & Medical Sciences (AREA)
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  • Chemical & Material Sciences (AREA)
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  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Dermatology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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  • Gastroenterology & Hepatology (AREA)
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  • Proteomics, Peptides & Aminoacids (AREA)
  • Marine Sciences & Fisheries (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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Abstract

L'invention concerne le domaine à la jonction de la médecine et de la pharmacologie et notamment la fabrication de produits médicamenteux et d'un procédé de cicatrisation accélérée de blessures d'armes à feu, au moyen de compositions à base de 2,6-di-tret-buthyl-4-méthylphénol. Elle concerne notamment une composition à base de gel destiné à soigner des blessures d'armes à feu qui comprend en tant que composants actifs 5-10 % en poids de 2,6-di-tret-buthyl-4-méthylphénol et 3-5 % en poids de carnosine. La deuxième composition de l'invention à base de gel comprend au lieu de carnosine3-5 % en poids de 'Molluskam'. L'invention concerne aussi une composition à base de gel destinée au traitement de blessures d'armes à feu, au moyen de compositions à base de gel avec 5-10 % en masse de 2,6-di-tret-buthyl-4-méthylphénol, 1-3 % en masse de T-activine et 1-3 % en masse de tomicidine. L'invention concerne aussi un procédé destiné à soigner des blessures d'armes à feu qui consiste à appliquer à la blessure une des compositions de l'invention en quantités efficaces, ce moyen de traitement étant appliqué pas plus tard que 12 heures après la blessure puis de nouveaux un à deux jours après la blessure. Le procédé destiné à soigner des blessures d'armes à feu de l'invention permet, grâce à l'action conjointe des composants faisant partie de la composition proposée, de réduire sensiblement la surface du foyer de la blessure et d'accélérer les processus de réparation, ce qui réduit le temps nécessaire à la cicatrisation de la blessure.
PCT/RU2007/000615 2007-06-01 2007-11-08 Compositions à base de 2,6-di-tret-buthyl-4-méthylphénol et procédé pour soigner des blessures par armes à feu les utilisant WO2008150190A1 (fr)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
RU2007120435 2007-06-01
RU2007120435/15A RU2367418C2 (ru) 2007-06-01 2007-06-01 Композит для лечения огнестрельных ран и способ лечения огнестрельных ран
RU2007120436 2007-06-01
RU2007120434/15A RU2367417C2 (ru) 2007-06-01 2007-06-01 Композит для лечения огнестрельных ран и способ лечения огнестрельных ран
RU2007120436/15A RU2367419C2 (ru) 2007-06-01 2007-06-01 Композит для лечения огнестрельных ран и способ лечения огнестрельных ран
RU2007120434 2007-06-01

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WO2008150190A1 true WO2008150190A1 (fr) 2008-12-11

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2223670C1 (ru) * 2002-07-30 2004-02-20 Федеральное государственное унитарное предприятие Тихоокеанский научно-исследовательский рыбохозяйственный центр Биологически активная добавка к пище
RU2005128993A (ru) * 2005-09-08 2007-03-20 Общество С Ограниченной Ответственностью Исследовательский Центр "Комкон" (Ru) Средство для коррекции стресс-индуцируемых нейромедиаторных, нейроэндокринных и метаболических нарушений, а также способ профилактики и лечения сопутствующих им паталогических состояний

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2223670C1 (ru) * 2002-07-30 2004-02-20 Федеральное государственное унитарное предприятие Тихоокеанский научно-исследовательский рыбохозяйственный центр Биологически активная добавка к пище
RU2005128993A (ru) * 2005-09-08 2007-03-20 Общество С Ограниченной Ответственностью Исследовательский Центр "Комкон" (Ru) Средство для коррекции стресс-индуцируемых нейромедиаторных, нейроэндокринных и метаболических нарушений, а также способ профилактики и лечения сопутствующих им паталогических состояний

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Title
MASHKOVSKY M.D.: "Lekarstvennye sredstva. M., OOO "NOVAYA GAZETA"", IZDATEL S.B. DIVOV, vol. 2, 2001, pages 191, 401 *
SHAPOSHNIKOV J.G. ET AL.: "Ognestrelnaya rana. Fiziko-khimicheskie i mediko-biologicheskie aspekty", M., NAUKA, 2002, pages 124 - 142 *

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