WO1999018083A1 - N,n'-(sulfonyldi-1, 4-phenylene) bis (n'',n''- dimethylformamidin)-1, 2,3,4-tetrahydro- 6-methyl-2, 4-dioxo-5-pyrimidinsulfonate stimulant le metabolisme cellulaire et possedant une action immunotrope et antibacterienne, et procede de production - Google Patents

N,n'-(sulfonyldi-1, 4-phenylene) bis (n'',n''- dimethylformamidin)-1, 2,3,4-tetrahydro- 6-methyl-2, 4-dioxo-5-pyrimidinsulfonate stimulant le metabolisme cellulaire et possedant une action immunotrope et antibacterienne, et procede de production Download PDF

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Publication number
WO1999018083A1
WO1999018083A1 PCT/RU1998/000314 RU9800314W WO9918083A1 WO 1999018083 A1 WO1999018083 A1 WO 1999018083A1 RU 9800314 W RU9800314 W RU 9800314W WO 9918083 A1 WO9918083 A1 WO 9918083A1
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WO
WIPO (PCT)
Prior art keywords
compounds
compound
methyl
dioxo
bis
Prior art date
Application number
PCT/RU1998/000314
Other languages
English (en)
Russian (ru)
Inventor
Alexandr Leonidovich Reshetov
Nikolai Mikhailovich Goloschapov
Elena Andreevna Michurina
Tamara Petrovna Filipskikh
Elena Nikolaevna Goloschapova
Ljubov Elizarovna Kostjuk
Tatyana Timofeevna Sudareva
Rakhim Musaevich Khaitov
Galina Ivanovna Tsyvkina
Original Assignee
Alexandr Leonidovich Reshetov
Goloschapov Nikolai Mikhailovi
Elena Andreevna Michurina
Tamara Petrovna Filipskikh
Elena Nikolaevna Goloschapova
Ljubov Elizarovna Kostjuk
Tatyana Timofeevna Sudareva
Rakhim Musaevich Khaitov
Galina Ivanovna Tsyvkina
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 Alexandr Leonidovich Reshetov, Goloschapov Nikolai Mikhailovi, Elena Andreevna Michurina, Tamara Petrovna Filipskikh, Elena Nikolaevna Goloschapova, Ljubov Elizarovna Kostjuk, Tatyana Timofeevna Sudareva, Rakhim Musaevich Khaitov, Galina Ivanovna Tsyvkina filed Critical Alexandr Leonidovich Reshetov
Priority to AU14476/99A priority Critical patent/AU1447699A/en
Priority to UA2000052577A priority patent/UA46163C2/uk
Priority to EA200000370A priority patent/EA002153B1/ru
Publication of WO1999018083A1 publication Critical patent/WO1999018083A1/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
    • C07D239/60—Three or more oxygen or sulfur 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
    • A61P31/04—Antibacterial agents
    • 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
    • A61P31/04—Antibacterial agents
    • A61P31/08—Antibacterial agents for leprosy
    • 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
    • A61P37/02—Immunomodulators
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C317/34—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring
    • C07C317/38—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring with the nitrogen atom of at least one amino group being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfones
    • C07C317/40—Y being a hydrogen or a carbon atom

Definitions

  • the invention is related to organic chemistry, and more precisely to the new biologically active compound -methyl-2, 4-dioxo-5-pyrimidine sulfate stimulating cellular metabolism and possessing immune and anti-inflammatory activity, and.
  • Chebny doses of these drugs should be reasonably high.
  • the claimed invention is new and is not described in the literature.
  • the main task of the invention was to create a new connection, easily dissolve in hot water and 0, 25% -0, 5% disruption, and increase the disruption
  • This compound stimulates cellular metabolism (exchange of substances), which is an increase in the quantity of protein, protein. At the same time, it stimulates the stimulating action of the hydrated diuciphene, diuciphene, and other basic substances.
  • This connection also shows the antimicrobial effect of the cure in treating leprosy mycobacterium, tuberculosis mycobacterium and hepatic mycobacterium.
  • the claimed compound is an amorphous green and yellow in color, a melting point of 245-247 ° C. It is easy to use in hot water, we dissolve in dimethylphamide, dimethyl sulfide, and we do not dissolve in ordinary organic products. The structure is supported by the data of I and II of the spectroscopy.
  • This compound is produced by heating the equimolecular amounts of diamine diphenylsulfone and 6-methyl-5-uracil-sulfulfide in dimethyl sulfamide.
  • ⁇ e ⁇ i ⁇ usl ⁇ viya ⁇ not ⁇ b ⁇ a- zue ⁇ sya, ⁇ a ⁇ m ⁇ zhn ⁇ would byl ⁇ ⁇ zhida ⁇ , sul ⁇ namidn ⁇ e ⁇ iz- v ⁇ dn ⁇ e diamin ⁇ di ⁇ enilsul ⁇ na (DDS), and in ⁇ e ⁇ vuyu ⁇ che ⁇ ed ide ⁇ vzaim ⁇ deys ⁇ vie diamin ⁇ di ⁇ enilsul ⁇ na with dime ⁇ il ⁇ ma- mid ⁇ m ( ⁇ 5, 3.133.078; 30 S ⁇ ⁇ eyyz.1 :, b. ⁇ .Sagz ⁇ , Ca ⁇ . ⁇ _ ⁇ vic_ ⁇ grain, 1965, ⁇ .43, ⁇ 9, ⁇ .26
  • the resulting dimethylphamidamide further develops salt from 6-methyl-acyl-5-sulfonic acid.
  • the claimed compound was tested in an experiment on animals. The advantages of the claimed connection in comparison with the diusional illustration of table 1. - 4 -
  • the number of compounds was divided into white, non-native mice weighing 18-20 g in a simple experience using the Litch-Field-Wilkson method (1).
  • the influence of the claimed compound on the exchange of live animals has been studied.
  • the study of the effect of the proposed product on the exchange of live car cells was compared with 6-methyl (methacyl), diuchenum and hydrated.
  • test compound significantly increases the weight of the liver, liver, and the spleen.
  • the test compound significantly increases the weight of the liver, liver, and the spleen.
  • the claimed compound 7.7 0.7 61.9 ⁇ 0.7
  • the first group is final: within 6 months, the mice of this group received through a probe 5 times a week 0.5 ml of extreme suspension.
  • Experienced live groups were received during the test period of the studied drugs at a dose of 50 mg in 0 0.5 ml of a crusty suspension of 5 times a week. After 6 months, the animals were clogged up with a digital bias, they were banned from the study, and there were no accidents.
  • bacteria were tested for 5 days, the infectious area was diluted in 2 ml of 0.1% albumin solution; from the 0.01 ml suspension, it was diluted, it was diluted, There are plenty of microbes on one mouse in each group. The results of the research are presented in Table 7.
  • the claimed compound 20 0.014 ⁇ 0.007 50 0.001 ⁇ a ⁇ sledue ⁇ of ⁇ ivedenny ⁇ secy ⁇ , zayavlyaem ⁇ e s ⁇ edine- of ⁇ bladae ⁇ vys ⁇ y ba ⁇ e ⁇ i ⁇ s ⁇ a ⁇ iches ⁇ y a ⁇ ivn ⁇ s ⁇ yu ⁇ n ⁇ - si ⁇ eln ⁇ mi ⁇ ba ⁇ e ⁇ y le ⁇ y, ⁇ ev ⁇ s ⁇ dyaschey an ⁇ imi ⁇ ba ⁇ e- ⁇ ialnuyu a ⁇ ivn ⁇ s ⁇ ⁇ a ⁇ diutsi ⁇ na, and ⁇ a ⁇ gid ⁇ a ⁇ a diutsi ⁇ na. Otherwise, it should be noted that 50% of the animals in the group, who received the treatment with the claimed compound, did not experience any disease that caused them to be ill.
  • the beneficial activity of the claimed compounds in comparison with methacyl, diuchene and hydrated diuciphone was studied on the microbial strain "Casseteta".
  • the basic therapy of tuberculosis was cultivated in a liquid environment of the School of Culture (6) with 10% human plasma. ⁇ schreib Each product containing 2 ml of medium with the studied substances in a different concentration was inoculated with 0, 2 ml of suspension of bacteriosis, and 10% of the disease was Incubated for 10 days ⁇ and 37 ° ⁇ .
  • the minimum inhibitory endoscopy was attributed to the absence of a small amount of tuberculosis disease in the case with the smallest content of the studied substance.
  • Crops are maintained at 34 ° C for 10 days, then 5 5 minutes are cultivated at 1,500 and 1,500.
  • the horticultural fluid is drained through the edge: the sediment is deposited on the glass, it is equally spread, fixed, and absorbed (8).
  • Table 9 means: + - availability of the unit. 5 - - lack of space. - single microbial therapy in a few field of vision. The investigated compounds are less than those of the comparison, and in most cases it is investigated with 0 percent concentration and the bactericidal effect is found in the solution. 1 and £ u.
  • the claimed compound increases the cost of administration (depending on the method of administration) by 3.8 and 4.8 times, which results in a 2-fold decrease in efficiency.
  • phased activity of the claimed compounds increases by more than 1.5 times, and when the amount of hydration is increased, it is 12–17% more active. Perhaps this is due to the practical complete inappropriateness of the water.
  • the Stimulation Index calculates the increase in the number of blasts in the experienced group to the number of blunders in the online group. In general, all the studied drugs stimulate the lymphocytes (the formation of the blinks), but the highest connection rate is the connection to the connection (23), which is 20 (); at diucion.
  • a flask containing 24.8 g (0.1 mol) of 4, 4-diamine di-phenyl sulfone in 300 ml of dry dimethylamide and stirring and temperature of 25-30 ° C is 0.25 (0.2) 47.3 ° C. 6-methyl-acyl-5-sulfonic acid. Stir for 1 hour at a temperature of 50-53 ° C, cool and filter the remaining plant. The raw product is stirred for 2 hours at a temperature of 200 ml. The yellow powder boils 1 hour in 250 ml
  • the claimed compound is ⁇ , ⁇ '- (sulfulfyldi-1, 4-phenylene) bis ( ⁇ ", ⁇ " -dimethylphammamidine) -1,2, 3, 4-tetrahydro-6-methyl-2, 4-dioxo-5-pyrimidine , s ⁇ imuli ⁇ ue ⁇ ⁇ le ⁇ chny Me- 25 ⁇ ab ⁇ lizm and ⁇ bladae ⁇ immun ⁇ n ⁇ y and an ⁇ imi ⁇ ba ⁇ e ⁇ ialn ⁇ y a ⁇ ivn ⁇ s ⁇ yu and na ⁇ di ⁇ ⁇ imenenie in medicine for the treatment of ⁇ aches ⁇ ve s ⁇ eds ⁇ va le ⁇ y, ⁇ ube ⁇ uleza and d ⁇ ugi ⁇ immun ⁇ de- ⁇ itsi ⁇ ny ⁇ zab ⁇ levany, chas ⁇ ⁇ sl ⁇ zhenny ⁇ mi ⁇ ba ⁇ e ⁇ ialnymi in ⁇ e ⁇ tsiyami.

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

Abstract

Cette invention concerne de nouveaux composés chimiques actifs sur le plan biologique, lesquels sont dérivés d'un diaminodiphénylsulfone et correspondent à la formule générale (1). Ces composés sont obtenus en faisant réagir des quantités équimoléculaires de diaminodiphénylsulfone et de 6-méthyluracylsulfochlorure dans du diméthylformamide. Ces composés ne sont pratiquement pas toxiques (LD50 = 3000 mg/kg) et sont actifs lors d'expériences portant sur les mycobactéries de la lèpre et de la tuberculose. Ces composés influent activement sur l'échange cellulaire, et peuvent être utilisés en qualité d'agents permettant de soigner la lèpre, la tuberculose, ainsi que d'autres états se traduisant par un déficit immunitaire.
PCT/RU1998/000314 1997-10-07 1998-10-05 N,n'-(sulfonyldi-1, 4-phenylene) bis (n'',n''- dimethylformamidin)-1, 2,3,4-tetrahydro- 6-methyl-2, 4-dioxo-5-pyrimidinsulfonate stimulant le metabolisme cellulaire et possedant une action immunotrope et antibacterienne, et procede de production WO1999018083A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
AU14476/99A AU1447699A (en) 1997-10-07 1998-10-05 N,n'-(sulphonyldi-1, 4-phenylen) bis (n'',n''- dimethylformamidin)-1, 2,3,4-tetrahydro- 6-methyl-2, 4-dioxo-5-pyrimidinsulphonate for stimulating cellular metabolism and having an immunotropic and anti-bacterial activity and method for producing the same
UA2000052577A UA46163C2 (uk) 1997-10-07 1998-10-05 N, n'-(сульфонілди-1,4-фенілен)біс(n",n"-диметилформамідин)-1,2,3,4-тетрагідро-6-метил-2,4-діоксо-5-піримідинсульфонат, що стимулює клітинний метаболізм і має імунотропну та антимікобактеріальну активність, і спосіб його отримання
EA200000370A EA002153B1 (ru) 1997-10-07 1998-10-05 N,n'-(сульфонилди-1,4-фенилен)бис(n'',n''-диметилформамидин)-1,2,3,4-тетрагидро-6-метил-2,4-диоксо-5-пиримидинсульфонат, стимулирующий клеточный метаболизм и обладающий иммунотропной и антимикобактериальной активностью, и способ его получения

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
RU97117514 1997-10-07
RU97117514A RU2136668C1 (ru) 1997-10-07 1997-10-07 N,n'-(сульфонилди-1,4-фенилен)бис(n'',n''- диметилформамидин)1,2,3,4-тетрагидро-6-метил-2,4- диоксо-5-пиримидинсульфонат, стимулирующий клеточный метаболизм и обладающий иммунотропной и антимикобактериальной активностью

Publications (1)

Publication Number Publication Date
WO1999018083A1 true WO1999018083A1 (fr) 1999-04-15

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/RU1998/000314 WO1999018083A1 (fr) 1997-10-07 1998-10-05 N,n'-(sulfonyldi-1, 4-phenylene) bis (n'',n''- dimethylformamidin)-1, 2,3,4-tetrahydro- 6-methyl-2, 4-dioxo-5-pyrimidinsulfonate stimulant le metabolisme cellulaire et possedant une action immunotrope et antibacterienne, et procede de production

Country Status (5)

Country Link
AU (1) AU1447699A (fr)
EA (1) EA002153B1 (fr)
RU (1) RU2136668C1 (fr)
UA (1) UA46163C2 (fr)
WO (1) WO1999018083A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001032650A2 (fr) * 1999-11-05 2001-05-10 Alexandr Leonidovich Reshetov Sels alcalins de n-(6-alkyle-2,4-dioxo-1,2,3,4-tetrahydro-5-pyrimidinesulfone)-n'-isonicotinoylhydrazide pouvant presenter une activite antimicrobienne et immunotrope, methode de preparation de ces sels, utilisation de ces sels comme immunomodulateurs et composition pharmaceutique a base de ces sels

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005092344A1 (fr) * 2004-03-26 2005-10-06 Zakrytoe Aktsionernoe Obschestvo 'novaya Linia' Preparation medicinale
RU2550948C1 (ru) * 2014-06-20 2015-05-20 Общество с ограниченной ответственностью "Научно-внедренческий центр "Агроветзащита" N,n'-(сульфонилди-п-фенилен)бис-n'',n''-диметилформамидин, обладающий акарицидным действием

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1511517A (en) * 1974-09-18 1978-05-17 Sirius Alpha-(diethylamino)-propiophenone orotate a process for its preparation and its use in pharmaceutical compositions
SU687074A1 (ru) * 1978-01-06 1979-09-25 2-Московский Ордена Ленина Государственный Медицинский Институт Им. Н.И.Пирогова 4-Амино-4 -дифенилсульфонаммониева соль 6-метил-2,4-диоксо-1,2,3,4тетрагидропиримидина, обладающа противолепрозной и противосудорожной активностью
RU2044728C1 (ru) * 1990-08-21 1995-09-27 Научно-исследовательская лаборатория иммунохимиотерапии лепры с опытно-экспериментальным производством иммуномодуляторов и клиниками ИДС Оротат гидразида изоникотиновой кислоты, обладающий антимикобактериальной и иммунотропной активностью

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1511517A (en) * 1974-09-18 1978-05-17 Sirius Alpha-(diethylamino)-propiophenone orotate a process for its preparation and its use in pharmaceutical compositions
SU687074A1 (ru) * 1978-01-06 1979-09-25 2-Московский Ордена Ленина Государственный Медицинский Институт Им. Н.И.Пирогова 4-Амино-4 -дифенилсульфонаммониева соль 6-метил-2,4-диоксо-1,2,3,4тетрагидропиримидина, обладающа противолепрозной и противосудорожной активностью
RU2044728C1 (ru) * 1990-08-21 1995-09-27 Научно-исследовательская лаборатория иммунохимиотерапии лепры с опытно-экспериментальным производством иммуномодуляторов и клиниками ИДС Оротат гидразида изоникотиновой кислоты, обладающий антимикобактериальной и иммунотропной активностью

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001032650A2 (fr) * 1999-11-05 2001-05-10 Alexandr Leonidovich Reshetov Sels alcalins de n-(6-alkyle-2,4-dioxo-1,2,3,4-tetrahydro-5-pyrimidinesulfone)-n'-isonicotinoylhydrazide pouvant presenter une activite antimicrobienne et immunotrope, methode de preparation de ces sels, utilisation de ces sels comme immunomodulateurs et composition pharmaceutique a base de ces sels
WO2001032650A3 (fr) * 1999-11-05 2002-05-10 Alexandr Leonidovich Reshetov Sels alcalins de n-(6-alkyle-2,4-dioxo-1,2,3,4-tetrahydro-5-pyrimidinesulfone)-n'-isonicotinoylhydrazide pouvant presenter une activite antimicrobienne et immunotrope, methode de preparation de ces sels, utilisation de ces sels comme immunomodulateurs et composition pharmaceutique a base de ces sels

Also Published As

Publication number Publication date
EA200000370A1 (ru) 2000-10-30
RU2136668C1 (ru) 1999-09-10
UA46163C2 (uk) 2002-05-15
AU1447699A (en) 1999-04-27
EA002153B1 (ru) 2001-12-24

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