WO2000029389A1 - 6-(3-carboxymethylphenyl)-amino-uracyle ayant une action biologique - Google Patents

6-(3-carboxymethylphenyl)-amino-uracyle ayant une action biologique Download PDF

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Publication number
WO2000029389A1
WO2000029389A1 PCT/RU1998/000387 RU9800387W WO0029389A1 WO 2000029389 A1 WO2000029389 A1 WO 2000029389A1 RU 9800387 W RU9800387 W RU 9800387W WO 0029389 A1 WO0029389 A1 WO 0029389A1
Authority
WO
WIPO (PCT)
Prior art keywords
compound
aminouracyl
new
carboxymethylphenyl
antiviral
Prior art date
Application number
PCT/RU1998/000387
Other languages
English (en)
Russian (ru)
Inventor
Elena Alexandrovna Izaxon
Original Assignee
Elena Alexandrovna Izaxon
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
Application filed by Elena Alexandrovna Izaxon filed Critical Elena Alexandrovna Izaxon
Priority to PCT/RU1998/000387 priority Critical patent/WO2000029389A1/fr
Priority to RU2001114504/04A priority patent/RU2207337C2/ru
Priority to AU26452/99A priority patent/AU2645299A/en
Publication of WO2000029389A1 publication Critical patent/WO2000029389A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
    • C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • 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
    • A61P31/18—Antivirals for RNA viruses for HIV
    • 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
    • A61P31/20—Antivirals for DNA viruses
    • A61P31/22—Antivirals for DNA viruses for herpes viruses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders

Definitions

  • the invention is related to medicine, more specifically, to pharmacology, veterinary medicine; Comparative - a synthetic, biologically active, 6-aminouracil-derived, which is potent and immune-stimulating.
  • the aforementioned derivative has an expressed activity as an industry, as well as an activity in case of viruses of an outgrowth.
  • the main purpose of the compound is to be used in medical practice.
  • the compound is indicated for the treatment of viral diseases caused by chlamydia, as well as diseases that are associated with immunodeficiency, in particular, malignant diseases. Otherwise, the recommended connection may be used in veterinary medicine - for the same purpose. Level of technology.
  • 6-aminouracil derivatives are known [2-7]. ⁇ parts in operation ⁇ . ⁇ .Kubtsova and others. [7] Allacyl (1-allyl-3-ethyl-6-aminouracil) is described as an active diuretic, which is used as a urea and is associated with an intermittent injury. This site is listed below. ⁇ ⁇ 00/29389 ⁇ / ⁇ 8 / 00387
  • 6-amine derivatives specific biological activity is indicated, which is described, in particular, in the work of D. D. ⁇ ashkovskogo [5] - see, for example, 6- [[3- [4- (2-Methoxyphenyl) -1- ⁇ -pyrazinyl] ⁇ yl] -amino] -1,3-dimethyl-acyl.
  • chemical, structural analogs of the new product are the derivatives of the 6-amine formula of the general formula
  • ⁇ phenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 4-bromophenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 2-methylphenyl, 3-methylphenyl, 1-on , 2-naphthyl, cyclohexyl [6].
  • Known sources of information do not contain information about any expressed biological activity. The closest to the claimed compound is a chemical structure -
  • the objective of the invention is the creation of a new substance that stimulates the production of endogenous interactions, as well as a non-hazardous, non-immune substance.
  • 6-aminouracil and named-6- (3-carboxymethylphenyl) aminouracil.
  • This chemical compound of the hetero-cyclic series is not related to the new group of the substituted 6-amine group.
  • the compound has a chemical formula (1)
  • connection structure has been proven by the method of
  • the claimed connection is new - there is no information in it from any of the available sources of information.
  • Zayavlyaem ⁇ e s ⁇ edinenie and eg ⁇ bi ⁇ l ⁇ giches ⁇ aya a ⁇ ivn ⁇ s ⁇ ne ⁇ chevidny for s ⁇ etsialis ⁇ a, is ⁇ dya i ⁇ ⁇ ivedenny ⁇ above information ⁇ b anal ⁇ ga ⁇ and ⁇ i ⁇ e having bi ⁇ l ⁇ giches ⁇ uyu a ⁇ ivn ⁇ s ⁇ in s ⁇ ve ⁇ shen ⁇ d ⁇ ug ⁇ y ⁇ blas ⁇ i, ni ⁇ a ⁇ ⁇ chevidnym ⁇ b ⁇ az ⁇ m not svyazann ⁇ y with the task iz ⁇ b ⁇ e ⁇ eniya.
  • the method of obtaining the target product is based on the interaction of a 6-coolant with the corresponding aromatic amine in the process.
  • ⁇ are signals of the primary group of the pyrimidine ring in the region of 10-12 ppm and metropolitan areas of the pyridine ring 4-6 ppm ⁇ SPECTRACHA ⁇ 13 C are characteristic signals from 3 70-100 ppm. - for carbon atoms of the aryl ring.
  • the caterpillar was added to the cages with a medium ⁇ -1640, containing 10% of calf food, which were received in a 96-well payment.
  • the initial concentration of the virus is 10-12 particles per ml.
  • the concentration of material and research ⁇ was 100, 10 and 1 mg / l.
  • the virus was removed and the medium was changed. The results were evaluated by the virulent effect of the virus on the cells after incubation at 38 ° C in the S ⁇ 2-incubator for 36 hours. ⁇ ⁇ 00/29389 ⁇ / ⁇ 8 / 00387
  • the induction of the synthesis of the compounds of the claimed preparation was carried out on the human culture of human lymphocytes.
  • a fresh health facility was used (no more than 12 hours after the fence).
  • Allocation of the limbs was carried out as follows.
  • the integrated circuit of the center was located in a density range of 1.71 g / cm l for the density of the fiber unit to isolate the function of the immune cells.
  • the indicated fraction after its treatment was divorced from a healthy environment ⁇ -1640.
  • the indicated nutritional product consisted of 5% fetal calf serum, 0.3 mg / ml L-glutamine, 100 units / ml penicillin, 50 mg / ml strutomycin.
  • Lymphocytes were overwhelmed with methyl blue in the chamber of Goryaev, after which they shared their accentuation. Concentrations of substances, after the corresponding dilutions of the original compounds of the claimed substances of healthy medium ⁇ -1640, were made in the range: 100 mg / l, 10 mg / l, 1 mg / l, 1 mg The final concentration of lymphocytes in the industrial mixture was 3 * 10 b cells / ml. Incubation of commercial and experimental products took 24 hours at 37 ° ⁇ .
  • Emulsions of the claimed compounds were prepared in different concentrations: 1500, 20, 5, 500, 100 mg.
  • 5 live animals were used.
  • the drug was injected one after the other through or through the internal.
  • the follow-up period was 14 days.
  • For control ⁇ ⁇ 00/29389 ⁇ / ⁇ 8 / 00387
  • the claimed compound has a low rate of rapid toxicity (L 5 ⁇ ) - 470 mg / kg.
  • the inventive connection is subject to the possibility of interruption in the use of medical devices, medications, and medical devices.
  • the results of the analysis show that the common methods of contact are used to clearly identify them.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Virology (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Animal Behavior & Ethology (AREA)
  • Communicable Diseases (AREA)
  • Molecular Biology (AREA)
  • Oncology (AREA)
  • Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • AIDS & HIV (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Immunology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Cette invention se rapporte au domaine de la médecine, plus précisément à celui de la pharmacologie, et concerne des substances synthétiques bioactives. Cette invention vise à traiter des maladies virales induites par des chlamydiae, ainsi que des maladies s'accompagnant d'un déficit immunitaire, notamment des tumeurs malignes. Le composé décrit dans cette invention peut en outre être utilisé en médecine vétérinaire. Cette invention a pour but de créer une nouvelle substance qui stimule la production d'interférons endogènes et qui possède une activité antivirale, à savoir une action de stimulation immunologique et antivirale. A cette fin, on procède à la synthèse d'un nouveau dérivé de 6-amino-uracyle et, plus précisément, à la synthèse d'un6-(3-carboxyméthylphényl)-amino-uracyle. Ce composé chimique de la série hétérocyclique appartient à un nouveau groupe de la classe des 6-aminopurines substitués et correspond à la formule (I). Cette invention concerne également un exemple de synthèse, des identifications, ainsi que des résultats d'expériences visant à déterminer les activités antivirale et immunomodulatrice ainsi que la toxicité de ce composé par rapport aux substances connues ayant une même vocation.
PCT/RU1998/000387 1998-11-18 1998-11-18 6-(3-carboxymethylphenyl)-amino-uracyle ayant une action biologique WO2000029389A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
PCT/RU1998/000387 WO2000029389A1 (fr) 1998-11-18 1998-11-18 6-(3-carboxymethylphenyl)-amino-uracyle ayant une action biologique
RU2001114504/04A RU2207337C2 (ru) 1998-11-18 1998-11-18 6-(3-ацетилфенил)аминоурацил
AU26452/99A AU2645299A (en) 1998-11-18 1998-11-18 6-(3-carboxymethylphenyl)-aminouracyl having a biological activity

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/RU1998/000387 WO2000029389A1 (fr) 1998-11-18 1998-11-18 6-(3-carboxymethylphenyl)-amino-uracyle ayant une action biologique

Publications (1)

Publication Number Publication Date
WO2000029389A1 true WO2000029389A1 (fr) 2000-05-25

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ID=20130294

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/RU1998/000387 WO2000029389A1 (fr) 1998-11-18 1998-11-18 6-(3-carboxymethylphenyl)-amino-uracyle ayant une action biologique

Country Status (3)

Country Link
AU (1) AU2645299A (fr)
RU (1) RU2207337C2 (fr)
WO (1) WO2000029389A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005103014A1 (fr) * 2004-04-20 2005-11-03 Viktor Veniaminovich Tets Sels de 2,4-dioxo-5-(2-hydroxy-3,5-dichloro-benzylidene)imino-1,3-pyrimidine
WO2012064222A1 (fr) * 2010-11-08 2012-05-18 Tets Viktor Veniaminovich Agent pour induire un interféron endogène

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SU1056900A3 (ru) * 1980-12-12 1983-11-23 Др.Карл Томэ Гмбх (Фирма) Способ получени пиримидинонов или их кислотно-аддитивных солей
EP0517181A1 (fr) * 1991-06-07 1992-12-09 Sumitomo Chemical Company, Limited Dérivés d'aminouraciles, leur production et usage
EP0700908A1 (fr) * 1994-07-19 1996-03-13 Japan Energy Corporation Dérivés de 1-arylpyrimidine et leur utilisation pharmaceutique

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SU1056900A3 (ru) * 1980-12-12 1983-11-23 Др.Карл Томэ Гмбх (Фирма) Способ получени пиримидинонов или их кислотно-аддитивных солей
EP0517181A1 (fr) * 1991-06-07 1992-12-09 Sumitomo Chemical Company, Limited Dérivés d'aminouraciles, leur production et usage
EP0700908A1 (fr) * 1994-07-19 1996-03-13 Japan Energy Corporation Dérivés de 1-arylpyrimidine et leur utilisation pharmaceutique

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005103014A1 (fr) * 2004-04-20 2005-11-03 Viktor Veniaminovich Tets Sels de 2,4-dioxo-5-(2-hydroxy-3,5-dichloro-benzylidene)imino-1,3-pyrimidine
WO2012064222A1 (fr) * 2010-11-08 2012-05-18 Tets Viktor Veniaminovich Agent pour induire un interféron endogène
EP2638901A1 (fr) * 2010-11-08 2013-09-18 Tets, Viktor Veniaminovich Agent pour induire un interféron endogène
US20130261302A1 (en) * 2010-11-08 2013-10-03 Viktor Veniaminovich Tets Agent for Inducing Endogenous Interferon
EP2638901A4 (fr) * 2010-11-08 2015-04-08 Tets Viktor Veniaminovich Agent pour induire un interféron endogène
US10029990B2 (en) 2010-11-08 2018-07-24 Viktor Veniaminovich Tets Agent for inducing endogenous interferon

Also Published As

Publication number Publication date
RU2001114504A (ru) 2004-03-20
RU2207337C2 (ru) 2003-06-27
AU2645299A (en) 2000-06-05

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