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WO1997002034A1 - Medicament anti-infectieux, anti-inflammatoire et antitumoral - Google Patents

Medicament anti-infectieux, anti-inflammatoire et antitumoral Download PDF

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Publication number
WO1997002034A1
WO1997002034A1 PCT/RU1996/000086 RU9600086W WO9702034A1 WO 1997002034 A1 WO1997002034 A1 WO 1997002034A1 RU 9600086 W RU9600086 W RU 9600086W WO 9702034 A1 WO9702034 A1 WO 9702034A1
Authority
WO
WIPO (PCT)
Prior art keywords
ppm
ρсτ
acid
hydrogen
alkenyl
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/RU1996/000086
Other languages
English (en)
Russian (ru)
Inventor
Oleg Viktorovich Travkin
Elena Vladimirovna Yakovleva
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Individual
Original Assignee
Individual
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 Individual filed Critical Individual
Priority to AU65367/96A priority Critical patent/AU6536796A/en
Priority to EA199800424A priority patent/EA000632B1/ru
Publication of WO1997002034A1 publication Critical patent/WO1997002034A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H9/00—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical
    • C07H9/02—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical the hetero ring containing only oxygen as ring hetero atoms
    • C07H9/04—Cyclic acetals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
    • C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
    • C07D219/06—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02—Acyclic radicals, not substituted by cyclic structures
    • C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical

Definitions

  • the traditional, immunomodulators are divided into two main groups: a) high molecular weight (polysaccharides, poli - nucleotides etc.), and small masses. b) low molecular weight (some abnormal impulses, nucleosides and other heterocycles). The molecular weight. Usually do not exceed 1000.
  • ⁇ nas ⁇ yaschemu v ⁇ emenn issled ⁇ van ⁇ b ⁇ lsh ⁇ e chisl ⁇ n ⁇ z ⁇ m ⁇ le ⁇ ulya ⁇ ny ⁇ immun ⁇ m ⁇ dulya ⁇ v in ⁇ aches ⁇ ve ⁇ entsialy ⁇ y ⁇ ⁇ a ⁇ ma ⁇ l ⁇ giches ⁇ i ⁇ s ⁇ eds ⁇ v for treating ⁇ yada vi ⁇ usny ⁇ , and ba ⁇ e ⁇ ialny ⁇ g ⁇ ib ⁇ vy ⁇ in (]) e ⁇ tsy and ⁇ a ⁇ zhe detection ⁇ a ⁇ s ⁇ ed ⁇ vann ⁇ g ⁇ tsi ⁇ i ⁇ siches ⁇ g ⁇ and ⁇ iv ⁇ v ⁇ s ⁇ ali ⁇ eln ⁇ g ⁇ de ⁇ s ⁇ viya.
  • the derivatives are acid: ⁇ -methylene-carboxy-9-acridine (acid, ⁇ ).
  • ⁇ in the form of sodium salt, rect is known under the names of camedones (neoevr).
  • the drug showed a high activity and treated a number of diseases caused. as it is, it is also ⁇ ⁇ - which contain ⁇ 0, for example, the viruses of the groups ⁇ 5U 1 and ⁇ 8U 2, they were completed by ⁇ i ⁇ , the forest of Semlica, Venezuelan province.
  • ⁇ s ⁇ zhaleniyu ⁇ azal ⁇ s, ch ⁇ ⁇ a ⁇ en ⁇ e ⁇ alnaya le ⁇ a ⁇ s ⁇ vennaya ⁇ ma e ⁇ g ⁇ ⁇ e ⁇ a ⁇ a ⁇ a ⁇ lichae ⁇ sya niz ⁇ y s ⁇ abiln ⁇ s ⁇ y ⁇ in ⁇ as ⁇ v ⁇ a ⁇ , ch ⁇ ⁇ vidim ⁇ mu svyazan ⁇ with inve ⁇ siey ⁇ -B5 glyu ⁇ amnpa v ⁇ dny ⁇ ⁇ as ⁇ v ⁇ a ⁇ , ⁇ e ⁇ e ⁇ dyascheg ⁇ in ⁇ ya ⁇ bliz ⁇ i ⁇ ⁇ s ⁇ en ⁇ yu amin ⁇ m ⁇ n ⁇ sa ⁇ a ⁇ id ⁇ v.
  • I is an urban radical with a large number of carbon atoms from 1 to 7;
  • the objective of the invention is the receipt of a new medicinal product that ensures a reduction in the above-listed disadvantages.
  • the task posed is resolved by the receipt of new functional compounds, salts of acidic acids and substituted minerals, in general 5 formulas: ⁇ ⁇ 97/02034 ⁇ / ⁇ 6 / 00086
  • X and ⁇ - hydrogen, hydroxy-, oxyalkyl-, alkoxy- groups with large carbon atoms 1 to 3;
  • alk alkenyl, aliphatic, heterocyclic or aromatic cycles, acyl radical
  • ⁇ . ,, ⁇ ., - that is, the hydrogen or halogen, oxen, carboxy, alkaline.
  • Table 3 Results of the study of the claimed drugs for the model of the experimental impairment of the length of the disease in comparison with the case of diabetes, the drug-i-drug; 0
  • Table 4 Influence of the introduction of the claimed drugs on the indicators that affect the active activity of the markers in relation to the condition of the acysa;
  • Table 5 Comparative study of the antimicrobial activity of the claimed compounds, manufacture and accessory component;
  • Table 6 Influence of the claimed drugs on the territory of the solid tourist Erlich in comparison with industrial and non-proprietary components
  • Table 7 Influence of the claimed drugs on the growth of leukemia ⁇ -3880 in comparison with the industrial and non-proprietary components.
  • ⁇ ⁇ ezul ⁇ a ⁇ e study zayavlyaemy ⁇ ⁇ imiches ⁇ i ⁇ s ⁇ edineni ⁇ B5 ⁇ s ⁇ y ⁇ ⁇ y ⁇ a ⁇ ⁇ edeleny ⁇ gi ⁇ siches ⁇ i ⁇ deys ⁇ vi ⁇ ⁇ e ⁇ a ⁇ a ⁇ v on ⁇ ganizm, ⁇ a ⁇ ⁇ in ⁇ eg ⁇ aln ⁇ mu ⁇ aza ⁇ elyu- death zhiv ⁇ ny ⁇ , ⁇ a ⁇ and ⁇ v ⁇ zdeys ⁇ viyu on ⁇ sn ⁇ vnye, zhiznenn ⁇ important sis ⁇ emy: ⁇ v, SS and TS ⁇ S.
  • the compounds When introduced intramuscularly, the compounds are rapidly absorbed to reach maximum concentrations through. 20-50 minutes.
  • the half-life of ⁇ ( ⁇ 50%) is, as 5 is 100-130 minutes, eliminated from the main body ⁇ ⁇ 97/02034 ⁇ / ⁇ 6 / 00086
  • the 50 synthesized compounds were 2–2.5 times lower than the sum of the LE 50, which was their components taken in 5 units.
  • a representative viscous hydrous fluid is blended with 21.6 g of ⁇ -hydrochloric acid in 170 ml of anhydrous acetic acid. The mixture is boiled with a reflux cooler for 40 minutes. For> ⁇ , the time of the 3-chloro- ⁇ -acid hydrous acid plant solution is completely discharged, the recovery will become inoperative.
  • the drugs were administered at a dose of 50 mg / kg for 4 hours before and in the second days after the infection of the laboratory animals, excluding 0 intramuscular administration.
  • ⁇ ⁇ azhd ⁇ m ⁇ y ⁇ e in ⁇ aches ⁇ ve ⁇ e ⁇ enens- ⁇ e ⁇ a ⁇ a ⁇ a is ⁇ lz ⁇ vali ⁇ ibamidil (vi ⁇ az ⁇ l) ⁇ y ⁇ allowed ⁇ ysam ⁇ e ⁇ aln ⁇ in d ⁇ ze YU ⁇ mg / ⁇ g ⁇ s ⁇ anda ⁇ n ⁇ i5 lechebn ⁇ - ⁇ ila ⁇ iches ⁇ n s ⁇ eme.
  • mice 19 - white and white mice weighing 10–12 g., And with direct contamination and on white ground mice weighing 35–50 g, infected internal rats.
  • a virulent strain of the viola virus of the virulence ⁇ i ⁇ which was used in many multicultural cages, was used. Evaluation of the eruptive activity was implicated in mice infected with doses of a virus of 25-50 B ⁇ and scattered with an infected dose of a virus of 250 B ⁇ .
  • the preparations introduced an intrinsic technique in the form of an emergency treatment (after 2 hours after infection and then 1 time after 3 days). Experiments were considered to be valid only for 100% death of animals in the area.
  • ⁇ ⁇ y ⁇ e in ⁇ aches ⁇ ve ⁇ e ⁇ e ⁇ ens- ⁇ e ⁇ a ⁇ a is ⁇ lz ⁇ vali ⁇ ibamidil (vi ⁇ az ⁇ l) ⁇ y vv ⁇ dili zhiv ⁇ nym d ⁇ ze to 100 mg / ⁇ g ⁇ ⁇ ⁇ y s ⁇ eme same.
  • the acceptable activity of the claimed drugs is 3-0- ( ⁇ , ⁇ , dimethylamine-n-industrial) - 1, 2: 5,6-di- Economics ⁇ -isopropylidene-9-drug-1 4) and 3-0- ( ⁇ , ⁇ , -diethylamine- (2'-isotubutyl) - 1, 2 - ⁇ -isopropo-pyridine- ⁇ £> - allo-puranoses 2 "-carboxy- ⁇ - methyl-carboxylic-9" Acidide (2 in Table 4) was studied in white non-native mice. The preparations were administered internally in doses: 25, 50 and 75 mg / kg of body weight was taken for the test.
  • the antibacterial action of the claimed drugs has been studied on the model of a chronic stasis system caused by the internal introduction of the prosthetics system.
  • the biceps were administered internally to the 25 and 50 mg / kg doses of the treatment (1 time per day for 5 days), and the treatment was taken after 5 days.
  • the animals scored the original furnace, homogenized and sowed the agar for registration of the number of cells ⁇ . Aigai ⁇ . After 72 hours of incubation, at 37 ° C, the number of large, large stakes was divided.
  • a solid tumor (UE) was transplanted into the cushion of the hind paw of male mice, weighing 18-20 g of the ⁇ and ⁇ 57 ⁇ 1 line, respectively in a quantity of 10 (6) ⁇ cells.
  • the leukemia ⁇ -388 was rehearsed internally in male mice of the ⁇ line in the quantity of Yu 1 cell. Beginning on the 3rd day of the prevention of EHE (both during the period of illness and its immediate elements), and from the 2nd day after the prevention of HIV-388.
  • the mice were administered daily intramuscularly with 0.1 ml of the preparation, and the lively animals were administered with 20, 100 and 250 mg.
  • Numeral - number of survivors the denominator - number of survivors; ⁇ in the dummy defense index
  • Patent Poland 139805 ⁇ AND C07 ⁇ 219/16, publ. 07/31/1987

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biotechnology (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Oncology (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Communicable Diseases (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Cette invention se rapporte au domaine de la médicine et des substances biologiquement actives. Cette invention concerne la production d'une préparation médicamenteuse ayant une activité thérapeutique accrue et de nombreuses qualités curatives, laquelle composition peut être utilisée dans la préparation de médicaments d'une grande stabilité. La nouveauté de cette invention tient à la production de sels d'acides acridonacétiques et d'éthers monosubstitués de monosaccharides correspondant à la formule générale (I) ou (II) où X et Z représentent un atome d'hydrogène ou des groupes hydroxy, oxyalkyl, alcoxy ayant de 1 à 3 atomes de carbone; W représente un atome d'hydrogène, alkyl, alcényl, des cycles aliphatique ou aromatique, ou un radical acyle; R1 et R2 représentent un atome d'hydrogène ou d'halogène, des substituents oxy, carboxy, alkyle ou aryle; R3 et R4 représentent un atome d'hydrogène, alkyl, alcényl, ou un substituant aromatique ou hétérocyclique; et, enfin n vaut de 1 à 18, de préférence de 2 à 6.
PCT/RU1996/000086 1996-04-10 1996-04-11 Medicament anti-infectieux, anti-inflammatoire et antitumoral Ceased WO1997002034A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU65367/96A AU6536796A (en) 1996-04-10 1996-04-11 Anti-infection, anti-inflammatory and anti-tumour drug
EA199800424A EA000632B1 (ru) 1996-04-10 1996-04-11 Средство противоинфекционного, противовоспалительного и противоопухолевого действия

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
RU96106515 1996-04-10
RU96106515A RU2118532C1 (ru) 1996-04-10 1996-04-10 Противоинфекционное, противовоспалительное и противоопухолевое лекарственное средство

Publications (1)

Publication Number Publication Date
WO1997002034A1 true WO1997002034A1 (fr) 1997-01-23

Family

ID=20178908

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/RU1996/000086 Ceased WO1997002034A1 (fr) 1996-04-10 1996-04-11 Medicament anti-infectieux, anti-inflammatoire et antitumoral

Country Status (4)

Country Link
AU (1) AU6536796A (fr)
EA (1) EA000632B1 (fr)
RU (1) RU2118532C1 (fr)
WO (1) WO1997002034A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2021503501A (ja) * 2017-11-20 2021-02-12 シリコン スワット インコーポレイテッド オキソアクリジニル酢酸誘導体および使用方法

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2153876C1 (ru) * 1999-02-09 2000-08-10 Цивинский Станислав Викторович Состав против грибковых заболеваний кожи и ногтей и способ его применения
RU2153352C1 (ru) * 1999-08-09 2000-07-27 Гончар Александр Михайлович Фармацевтическая композиция, обладающая ранозаживляющим и противовоспалительным действием
RU2197248C2 (ru) * 2001-03-20 2003-01-27 Травкин Олег Викторович Лекарственный препарат, обладающий иммуномоделирующим, иммунокоррегирующим, противопаразитарным, противосклеротическим, противовирусным, противобактериальным, противогрибковым, противовоспалительным и противоопухолевым действием, и способ его приготовления
US7393862B2 (en) * 2002-05-17 2008-07-01 Celgene Corporation Method using 3-(4-amino-1-oxo-1,3-dihydro-isoindol-2-yl)-piperidine-2,6-dione for treatment of certain leukemias
RU2228757C1 (ru) * 2002-11-13 2004-05-20 Общество с ограниченной ответственностью "Арсентех" Противоопухолевое средство
US11414387B2 (en) 2017-11-20 2022-08-16 Stingthera, Inc. Oxoacridinyl acetic acid derivatives and methods of use

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1473169A (fr) * 1973-07-24 1977-05-11
DE2759468A1 (de) * 1977-08-29 1979-06-07 Sterling Drug Inc Acridinonverbindungen und ihre herstellung
EP0494623A1 (fr) * 1991-01-11 1992-07-15 Laboratoires Glaxo Sa Dérivés d'acridine
WO1994022837A1 (fr) * 1993-04-01 1994-10-13 Limited Liability Partnership 'polysan' N-METHYLE-N-/α,Δ-GLUCOPYRANOZIL/AMMONIAC-2-/ACRIDON-9-ON-10-YLE/ACETATE/CYCLOPHERONE DOTEE DE PROPRIETES DE PRODUCTION D'INTERFERON, ANTIVIRALES (Y COMPRIS L'ACTIVITE ANTI-VIH), ANTIPARASITAIRES, ANTI-PROMOTEUR ET RADIOPROTECTRICES

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4735934A (en) * 1981-02-17 1988-04-05 Greenwich Pharmaceuticals Incorporated Method of therapeutically treating a warm blooded animal afflicted with an autoimmune disease

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1473169A (fr) * 1973-07-24 1977-05-11
DE2759468A1 (de) * 1977-08-29 1979-06-07 Sterling Drug Inc Acridinonverbindungen und ihre herstellung
EP0494623A1 (fr) * 1991-01-11 1992-07-15 Laboratoires Glaxo Sa Dérivés d'acridine
WO1994022837A1 (fr) * 1993-04-01 1994-10-13 Limited Liability Partnership 'polysan' N-METHYLE-N-/α,Δ-GLUCOPYRANOZIL/AMMONIAC-2-/ACRIDON-9-ON-10-YLE/ACETATE/CYCLOPHERONE DOTEE DE PROPRIETES DE PRODUCTION D'INTERFERON, ANTIVIRALES (Y COMPRIS L'ACTIVITE ANTI-VIH), ANTIPARASITAIRES, ANTI-PROMOTEUR ET RADIOPROTECTRICES

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2021503501A (ja) * 2017-11-20 2021-02-12 シリコン スワット インコーポレイテッド オキソアクリジニル酢酸誘導体および使用方法

Also Published As

Publication number Publication date
EA000632B1 (ru) 1999-12-29
AU6536796A (en) 1997-02-05
RU2118532C1 (ru) 1998-09-10
EA199800424A1 (ru) 1999-02-25

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