WO1990012013A1 - NOUVELLES 1,2,3-TRIAZOLO-PYRIDO[2,1-b]QUINAZOLINES, LEUR PRODUCTION ET MEDICAMENTS LES CONTENANT - Google Patents

NOUVELLES 1,2,3-TRIAZOLO-PYRIDO[2,1-b]QUINAZOLINES, LEUR PRODUCTION ET MEDICAMENTS LES CONTENANT Download PDF

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Publication number
WO1990012013A1
WO1990012013A1 PCT/EP1990/000484 EP9000484W WO9012013A1 WO 1990012013 A1 WO1990012013 A1 WO 1990012013A1 EP 9000484 W EP9000484 W EP 9000484W WO 9012013 A1 WO9012013 A1 WO 9012013A1
Authority
WO
WIPO (PCT)
Prior art keywords
formula
compounds
triazolo
radical
atoms
Prior art date
Application number
PCT/EP1990/000484
Other languages
German (de)
English (en)
Inventor
Kurt Schromm
Helmut Ensinger
Original Assignee
Boehringer Ingelheim Kg
Boehringer Ingelheim International Gmbh
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 Boehringer Ingelheim Kg, Boehringer Ingelheim International Gmbh filed Critical Boehringer Ingelheim Kg
Publication of WO1990012013A1 publication Critical patent/WO1990012013A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
    • C07D471/14—Ortho-condensed systems

Definitions

  • the invention relates to new 1,2,3-triazolo-pyrido
  • Processes can be produced and which can be used as active ingredients in medicinal products.
  • R 1 for H, R, HCO, R-CO, RNH-CO, RO-CO or R-SO 2 ,
  • R 2 stands for H, R or R-CO and the entire group
  • R 1 R 2 N also for a 3 to 7-membered, saturated or unsaturated ring which can be substituted by one or two oxo groups and optionally one or two hydroxyl groups or can be condensed with a benzene ring, and R for an optionally hydroxyl and / or carboxy-substituted aliphatic radical with up to 12 C-atoms, a cycloaliphatic radical with 3 to 7 C-atoms, an aryl- or aryloxy-substituted aliphatic radical with a total of up to 12 C-atoms,
  • the aliphatic radicals can be straight-chain or
  • Chain length - also be mono- or polyunsaturated and possibly also contain a triple bond.
  • R 2 preferably represents H or an aliphatic radical having up to 8 carbon atoms. As far as the radicals R hydroxy and / or
  • carboxy-substituted it can be, for example, groups derived from glycolic, succinic, lactic, citric, tartaric or maleic acid.
  • unsaturated aliphatic substituents on nitrogen the double bond is in the
  • Aliphatic residues of this type are e.g. Allyl, propargyl. Contains R aromatic systems, e.g. a benzene ring, these can also be substituted one or more times, in particular by halogen,
  • R 1 and R 2 have the above meanings.
  • R 1 stands primarily for the groups R-CO and R-NH-CO, where R is a straight-chain or branched aliphatic radical with up to 8 C atoms, which can also be phenyl-substituted, a phenyl radical or a
  • the group R 1 R 2 N means one
  • the new compounds can be produced using chemical analogy processes, in particular as follows:
  • the reaction can take place in the melt at 120-200 ° C, preferably 160-175 ° C, or in
  • the starting materials IV for process 1 can e.g. be constructed as follows:
  • the starting materials of formula V are, for example, from the corresponding Nitro compounds prepared by process 1 or by nitration and reduction from the compounds of the formula VI:
  • ischemia e.g. cardiac, cerebral, gastrointestinal, renal, pulmonary ischemia and in diseases such as Crohn's disease, ulcerative colitis, arthritis, pancreatitis or Lesch-Nyphan syndrome.
  • the new compounds are also anti-allergic.
  • the therapeutic dose depends on the
  • the dose for adults is between 0.1 and 100 mg for oral administration and 0.01-10 mg for intravenous administration. It is used in the form of conventional pharmaceutical preparations such as capsules, tablets,
  • the inhibitory values (K. values) of the new compounds are approximately three orders of magnitude lower than for the gout agent allopurinol, as can be seen from the table below
  • the mixture is then cooled to 20 ° C. and mixed with 50 ml of 2.5% ammonia water, stirred for 10 minutes and acidified with 7.5 ml of glacial acetic acid.
  • the precipitated crystals are filtered off and washed well with water.
  • the raw material obtained is recrystallized from 40 times the amount of dimethylformamide.
  • the mixture is then cooled to 20 ° C., acidified with 7 ml of glacial acetic acid and diluted with 100 ml of water.
  • the precipitate is filtered off and recrystallized twice from dimethylformamide.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

Des composés ayant la formule (I), définie dans la description, peuvent être produits par des procédés usuels et être utilisés à des fins thérapeutiques.
PCT/EP1990/000484 1989-04-13 1990-03-26 NOUVELLES 1,2,3-TRIAZOLO-PYRIDO[2,1-b]QUINAZOLINES, LEUR PRODUCTION ET MEDICAMENTS LES CONTENANT WO1990012013A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP3912092.9 1989-04-13
DE19893912092 DE3912092A1 (de) 1989-04-13 1989-04-13 Neue pyridotriazole, ihre herstellung und sie enthaltende arzneimittel

Publications (1)

Publication Number Publication Date
WO1990012013A1 true WO1990012013A1 (fr) 1990-10-18

Family

ID=6378567

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1990/000484 WO1990012013A1 (fr) 1989-04-13 1990-03-26 NOUVELLES 1,2,3-TRIAZOLO-PYRIDO[2,1-b]QUINAZOLINES, LEUR PRODUCTION ET MEDICAMENTS LES CONTENANT

Country Status (3)

Country Link
AU (1) AU5331890A (fr)
DE (1) DE3912092A1 (fr)
WO (1) WO1990012013A1 (fr)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0113911A1 (fr) * 1983-01-08 1984-07-25 Boehringer Ingelheim Kg Pyrido-triazoloquinazolines, leur préparation et utilisation
DE3704203A1 (de) * 1987-02-11 1988-08-25 Boehringer Ingelheim Kg Verwendung von oxochinazolinderivaten bei der behandlung der hyperurikaemie

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0113911A1 (fr) * 1983-01-08 1984-07-25 Boehringer Ingelheim Kg Pyrido-triazoloquinazolines, leur préparation et utilisation
DE3704203A1 (de) * 1987-02-11 1988-08-25 Boehringer Ingelheim Kg Verwendung von oxochinazolinderivaten bei der behandlung der hyperurikaemie

Also Published As

Publication number Publication date
AU5331890A (en) 1990-11-05
DE3912092A1 (de) 1990-10-18

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