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WO2007120079A3 - 4-aminomethyl-6-bromine-5-hydroxyindol-3-carboxilate derivatives, method for the production (variants) and the use thereof - Google Patents

4-aminomethyl-6-bromine-5-hydroxyindol-3-carboxilate derivatives, method for the production (variants) and the use thereof Download PDF

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Publication number
WO2007120079A3
WO2007120079A3 PCT/RU2007/000179 RU2007000179W WO2007120079A3 WO 2007120079 A3 WO2007120079 A3 WO 2007120079A3 RU 2007000179 W RU2007000179 W RU 2007000179W WO 2007120079 A3 WO2007120079 A3 WO 2007120079A3
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
derivatives
carboxilate
hydroxyindol
aminomethyl
Prior art date
Application number
PCT/RU2007/000179
Other languages
French (fr)
Russian (ru)
Other versions
WO2007120079A2 (en
Inventor
Rakhimdzhan Akhmetdzhan Roziev
Jury Grigorievich Verkhovsky
Fedor Alexandrovich Trofimov
Nina Gavrilovna Tsyshkova
Elena Sergeevna Shevchenko
Elena Ivanovna Burtseva
Anatoliy Fedorovich Tsyb
Original Assignee
Obschestvo S Ogranichennoy Otv
Rakhimdzhan Akhmetdzhan Roziev
Jury Grigorievich Verkhovsky
Fedor Alexandrovich Trofimov
Nina Gavrilovna Tsyshkova
Elena Sergeevna Shevchenko
Elena Ivanovna Burtseva
Anatoliy Fedorovich Tsyb
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 Obschestvo S Ogranichennoy Otv, Rakhimdzhan Akhmetdzhan Roziev, Jury Grigorievich Verkhovsky, Fedor Alexandrovich Trofimov, Nina Gavrilovna Tsyshkova, Elena Sergeevna Shevchenko, Elena Ivanovna Burtseva, Anatoliy Fedorovich Tsyb filed Critical Obschestvo S Ogranichennoy Otv
Publication of WO2007120079A2 publication Critical patent/WO2007120079A2/en
Publication of WO2007120079A3 publication Critical patent/WO2007120079A3/en

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Classifications

    • 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
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses

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

Abstract

The invention relates to medicine, in particular to antiviral prophylactic and therapeutic agents and to methods for the production thereof. The inventive agents are embodied in the form of 4-aminomethyl-6-bromine-5-hydroxyindol-3-carboxilate derivatives of general formula (I), wherein R is alkyl, aryl, cyclohexyl, cycloheptyl, R1-C1-C3-alkyl, CH2-X-C1-C5-alkyl, CH2-X-C1-C5-aryl, CH2-X-C1-C5-heterocycle, X is N, O, S, R2 is C1-C5-alkyl, R3 and R4 have equal CH3 or C1-C5-alkyl value, NR3R4 is a 5-10-membered heterocycle which can contain N, O, S in the form of a heteroatom. The methods for producing said derivatives and the use thereof and the salts thereof for preparing medicinal agents for treating influenza of type A or B are also disclosed. The technical result consists of the extended range of antiviral activity.
PCT/RU2007/000179 2006-04-18 2007-04-13 4-aminomethyl-6-bromine-5-hydroxyindol-3-carboxilate derivatives, method for the production (variants) and the use thereof WO2007120079A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
RU2006112818/04A RU2330018C2 (en) 2006-04-18 2006-04-18 Derivative 4-aminomethyl-6-bromine-5-hydroxyindole-3-carboxylate, methods of their obtaining (versions) and their application
RU2006112818 2006-04-18

Publications (2)

Publication Number Publication Date
WO2007120079A2 WO2007120079A2 (en) 2007-10-25
WO2007120079A3 true WO2007120079A3 (en) 2008-01-10

Family

ID=38609926

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/RU2007/000179 WO2007120079A2 (en) 2006-04-18 2007-04-13 4-aminomethyl-6-bromine-5-hydroxyindol-3-carboxilate derivatives, method for the production (variants) and the use thereof

Country Status (2)

Country Link
RU (1) RU2330018C2 (en)
WO (1) WO2007120079A2 (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2387642C2 (en) * 2007-10-31 2010-04-27 Общество С Ограниченной Ответственностью "Бинатех" 5-substituted indole-3-carboxylic acid derivatives, having antiviral activity, synthesis method thereof and use
RU2386616C2 (en) * 2008-04-23 2010-04-20 Общество С Ограниченной Ответственностью "Бинатех" Derivatives of 5-hydroxy-4-aminomethyl-1-cyclohexyl (or cycloheptyl)-3-alkoxycarbonylindoles, pharmaceutically acceptable salts thereof, having antiviral activity and method of producing said compounds
RU2440114C9 (en) * 2010-10-05 2012-06-27 Общество С Ограниченной Ответственностью "Научно-Исследовательская Компания "Медбиофарм" Agent for influenza b virus
RU2435582C1 (en) * 2010-10-05 2011-12-10 Общество С Ограниченной Ответственностью "Научно-Исследовательская Компания "Медбиофарм" Medication against b influenza virus

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63188665A (en) * 1987-01-30 1988-08-04 Yoshitomi Pharmaceut Ind Ltd 5-hydroxyindole-3-carboxylic acid ester compound
SU1685933A1 (en) * 1974-11-27 1991-10-23 Всесоюзный Научно-Исследовательский Химико-Фармацевтический Институт Им.С.Орджоникидзе Chlorohydrate of 1-methyl-2-phenylthiomethyl-3-carboethoxy-4 -dimethylaminomethyl-5-oxy-6-bromoindole having antivirus action and method for obtaining it
RU2008004C1 (en) * 1986-06-25 1994-02-28 Центр по химии лекарственных средств - ВНИХФИ Prophylactic and curative agent for treating flu virus b
CN1482118A (en) * 2003-01-04 2004-03-17 沈阳药科大学 Novel 5-hydroxy-3-carboxylate indoles derivant and method for preparing the same
RU2256451C1 (en) * 2004-04-21 2005-07-20 Закрытое акционерное общество "Мастерлек" Medicinal agent for treatment of atypical pneumonia
CN1660807A (en) * 2004-01-07 2005-08-31 沈阳药科大学 New 5-hydroxy indole-3-ramification of carboxylic esters
WO2005087729A1 (en) * 2004-03-12 2005-09-22 Shenyang Pharmaceutical University 5-hydroxyindole-3-carboxylates derivatives and their use

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SU1685933A1 (en) * 1974-11-27 1991-10-23 Всесоюзный Научно-Исследовательский Химико-Фармацевтический Институт Им.С.Орджоникидзе Chlorohydrate of 1-methyl-2-phenylthiomethyl-3-carboethoxy-4 -dimethylaminomethyl-5-oxy-6-bromoindole having antivirus action and method for obtaining it
RU2008004C1 (en) * 1986-06-25 1994-02-28 Центр по химии лекарственных средств - ВНИХФИ Prophylactic and curative agent for treating flu virus b
JPS63188665A (en) * 1987-01-30 1988-08-04 Yoshitomi Pharmaceut Ind Ltd 5-hydroxyindole-3-carboxylic acid ester compound
CN1482118A (en) * 2003-01-04 2004-03-17 沈阳药科大学 Novel 5-hydroxy-3-carboxylate indoles derivant and method for preparing the same
CN1660807A (en) * 2004-01-07 2005-08-31 沈阳药科大学 New 5-hydroxy indole-3-ramification of carboxylic esters
WO2005087729A1 (en) * 2004-03-12 2005-09-22 Shenyang Pharmaceutical University 5-hydroxyindole-3-carboxylates derivatives and their use
RU2256451C1 (en) * 2004-04-21 2005-07-20 Закрытое акционерное общество "Мастерлек" Medicinal agent for treatment of atypical pneumonia

Non-Patent Citations (9)

* Cited by examiner, † Cited by third party
Title
DATABASE CHEMCATS [online] accession no. STN *
MEZENTSEVA M.V. ET AL.: "Sintez i protivovirusnaya aktivnost 2-anilino-metilnykh poizvodnykh 5-oxiindola", KHIMIKO-FARMATSEVTICHESKY ZHURNAL. MOSCOW, no. 10, 1990, pages 52 - 53 *
MEZENTSEVA M.V. ET AL.: "Sintez i protivovirusnaya aktivnost 2-fenoxi-metilnykh proizvodnykh 5-oxiindola", KHIMIKO-FARMATSEVTICHESKY ZHURNAL. MOSCOW, no. 5, 1991, pages 35 - 37 *
PANISHEVA E.K. ET AL.: "Sintez i biologicheskaya aktivnost zameschennykh 5-oxi-6-bromindola", KHIMIKO-FARMATSEVTICHESKY ZHURNAL. MOSCOW, no. 5, 1988, pages 565 - 569 *
RAGHAVENDRA GJOSHI ET AL.: "Synthesis and antimicrobial activity of some new 4-isogramines, 4-arylthiomethyl and 4-arylazo derivatives of 5-hydroxyindoles", JOURNAL OF THE INDIAN CHEMICAL SOCIETY, vol. 71, no. 4, pages 175 - 178 *
TROFIMOV F.A. ET AL.: "Sintez novogo protivovirusnogo preparata - arbidola", KHIMIKO-FARMATSEVTICHESKY ZHURNAL. MOSCOW, vol. 27, no. 1, 1993, pages 70 - 71 *
WANG DUN ET AL.: "Syntheses and the in vitro antiviral activities of the derivatives of o-bromo-S-hydroxyindole-S-carboxylic acid ethyl ester", CHINESE JOURNAL OF MEDICINAL CHEMISTRY, vol. 13, no. 4, 2003, pages 200 - 204 *
YAN FANG ZHAO: "Synthesis and anti-influenza virus activity of ethyl o-bromo-S-hydroxyindole-S-carboxylate derivatives", CHINESE CHEMICAL LETTERS, vol. 15, no. 9, pages 1039 - 1042, XP009126933 *
ZOTOVA S.A. ET AL.: "Sintez i biologicheskaya aktivnost zameschennykh sulfidov indola i benzofurana", KHIMIKO-FARMATSEVTICHESKY ZHURNAL, vol. 26, no. 1, pages 52 - 55 *

Also Published As

Publication number Publication date
RU2330018C2 (en) 2008-07-27
WO2007120079A2 (en) 2007-10-25
RU2006112818A (en) 2007-11-10

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