GB1023720A - as-triazino (5,6-b)indoles - Google Patents

as-triazino (5,6-b)indoles

Info

Publication number
GB1023720A
GB1023720A GB3519064D GB3519064D GB1023720A GB 1023720 A GB1023720 A GB 1023720A GB 3519064 D GB3519064 D GB 3519064D GB 3519064 D GB3519064 D GB 3519064D GB 1023720 A GB1023720 A GB 1023720A
Authority
GB
United Kingdom
Prior art keywords
alkyl
group
aralkyl
thiosemicarbazone
salts
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.)
Expired
Application number
GB3519064D
Inventor
Jan Mieczyslaw Zygmunt Gladych
John Harold Hunt
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.)
Allen and Hanburys Ltd
Original Assignee
Allen and Hanburys Ltd
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 Allen and Hanburys Ltd filed Critical Allen and Hanburys Ltd
Priority to GB3519064D priority Critical patent/GB1023720A/en
Priority claimed from GB36551/63A external-priority patent/GB1023205A/en
Publication of GB1023720A publication Critical patent/GB1023720A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • 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
    • 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
    • C07D209/32—Oxygen atoms
    • C07D209/38—Oxygen atoms in positions 2 and 3, e.g. isatin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
    • C07D487/14—Ortho-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (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 comprises compounds of the general formula <FORM:1023720/C2/1> and their pharmaceutically acceptable salts wherein R1 is H or a halogen atom or an alkyl, aralkyl, OH, alkoxy, NO2, NH2 or CF3 group, R2 is H or an alkyl or aralkyl group, X is O, S, SO, SO2 or NR3, where R3 is H, or a methyl group, Z is an alkyl, alkenyl, aryl or aralkyl group or a group of the formula AlkOH or AlkNR4R5, where Alk is a branched or straight-chain alkylene radical of 2-10 C and R4 and R5 are H or alkyl groups or together with the adjacent N form a heterocyclic ring which may contain additional hetero atoms or Z is H when X is O or S, or Z is NH2 when X is NH, or X-Z together form an N-containing ring linked through the ring N, or X-Z together represent H and the preparation thereof by cyclizing an isatin b -thiosemicarbazone to give a 3-mercapto-as-triazino-(5,6-b) indole and, if desired, replacing -SH by X-Z or converting SH into -X-Z. Alternatively the products of the invention are prepared by reacting isatin and thiosemicarbazone without isolating the thiosemicarbazide. Salts of the invention include quaternary ammonium salts. Pharmaceutical compositions having antiviral and anti-bacterial properties comprise the compounds of the invention and a carrier therefor, and may be formulated as tablets, capsules, suppositories, and solutions for injection.
GB3519064D 1963-09-17 1963-09-17 as-triazino (5,6-b)indoles Expired GB1023720A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB3519064D GB1023720A (en) 1963-09-17 1963-09-17 as-triazino (5,6-b)indoles

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GB36551/63A GB1023205A (en) 1963-09-17 1963-09-17 -triazino(5,6-6) indoles
GB3519064D GB1023720A (en) 1963-09-17 1963-09-17 as-triazino (5,6-b)indoles
GB716964 1964-02-20
GB716864 1964-02-20

Publications (1)

Publication Number Publication Date
GB1023720A true GB1023720A (en) 1966-03-23

Family

ID=27447580

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3519064D Expired GB1023720A (en) 1963-09-17 1963-09-17 as-triazino (5,6-b)indoles

Country Status (1)

Country Link
GB (1) GB1023720A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3444298A (en) * 1967-07-20 1969-05-13 Smithkline Corp Method for preventing rhinovirus infections with 3-(3-hydroxy-3-methylbutyl-amino) - 5 - methyl - 5h - as - triazino(5,6-b) indole
US3452013A (en) * 1964-08-27 1969-06-24 Allen & Hanburys Ltd As-triazino(5,6-b)indoles
EP0921803A1 (en) * 1997-02-21 1999-06-16 Viropharma Incorporated Methods for preventing and treating pestivirus infection and associated diseases
WO2005033109A1 (en) * 2003-10-03 2005-04-14 Sumitomo Chemical Company, Limited Triazinoindolamine compound
WO2013041859A1 (en) * 2011-09-19 2013-03-28 Isis Innovation Limited Cannabinoid-2-receptor agonists
WO2015057175A1 (en) 2013-10-15 2015-04-23 Ústav Experimentálnej Farmakológie A Toxikológie Sav Use of 5-carboxymethyl-3-mercapto-1,2,4-triazino-[5,6-b]indoles and their pharmaceutical composition

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3452013A (en) * 1964-08-27 1969-06-24 Allen & Hanburys Ltd As-triazino(5,6-b)indoles
US3444298A (en) * 1967-07-20 1969-05-13 Smithkline Corp Method for preventing rhinovirus infections with 3-(3-hydroxy-3-methylbutyl-amino) - 5 - methyl - 5h - as - triazino(5,6-b) indole
EP0921803A1 (en) * 1997-02-21 1999-06-16 Viropharma Incorporated Methods for preventing and treating pestivirus infection and associated diseases
EP0921803A4 (en) * 1997-02-21 2003-04-02 Viropharma Inc Methods for preventing and treating pestivirus infection and associated diseases
WO2005033109A1 (en) * 2003-10-03 2005-04-14 Sumitomo Chemical Company, Limited Triazinoindolamine compound
WO2013041859A1 (en) * 2011-09-19 2013-03-28 Isis Innovation Limited Cannabinoid-2-receptor agonists
WO2015057175A1 (en) 2013-10-15 2015-04-23 Ústav Experimentálnej Farmakológie A Toxikológie Sav Use of 5-carboxymethyl-3-mercapto-1,2,4-triazino-[5,6-b]indoles and their pharmaceutical composition

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