Triazoloquinazolines, their preparation and use

Details Triazoloquinazolines, their preparation and use Triazoloquinazolines, their preparation and use

1995-06-01

1997-05-20

Ford, John M.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

544247, 544251, 514257, C07D48704, A61K 31495

Patent

active

056312610

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to novel triazoloquinazolines, to a process for their preparation and to their use for controlling diseases.
Pyrazolo- and triazoloquinazolines having antiallergic and antiinflammatory properties have been disclosed (EP 80,176, U.S. Pat. Nos. 4,053,600, 4,128,644). Pyrazoloquinazolines which are additionally suitable for treating thrombosis and neurological disorders have also been disclosed (U.S. Pat. No. 5,153,196).
We have now found that triazoloquinaolines of the formula I ##STR2## where
A is C.sub.1-5 -alkylene,
X is carboxyl which can be in the form of its salt with a physiologically tolerated amine cation or metal cation; the radical ##STR3## where R.sup.4 is C.sub.1-8 -alkyl, cycloalkyl with 3 to 8 carbon atoms in the ring, benzyl, one of the radicals --(CH.sub.2).sub.n --O--R.sup.5 or ##STR4## where n is the number 2, 3 or 4 and
R.sup.5 and R.sup.6 are each C.sub.1-3 -alkyl; hydroxyl, C.sub.1-4 -hydroxyalkyl, C.sub.1-4 -alkylcarbonyl, nitrile O--C.sub.1-4 -alkyl, tetrazolyl, carbonylaminotetrazole or unsubstituted or substituted carbamoyl, and
R.sup.1 and R.sup.2, which can be identical or different, are each hydrogen, fluorine, chlorine or bromine, trifluoromethyl, cyano, nitro, amino, C.sub.1-5 -alkyl, mono- or di-C.sub.1-5 -alkylamino, C.sub.1-6 -alkylthio, C.sub.1-6 -alkylsulfenyl, C.sub.1-6 -alkylsulfonyl, aminosulfonyl, di-C.sub.1-6 -alkylaminosulfonyl, or
R.sup.1 and R.sup.2 together are methylene- or ethylenedioxy or straight-chain C.sub.3-5 -alkylene, or an aromatic or heterocyclic ring, show a different spectrum of effects.
Preferred compounds of the formula I are those where A and X have the stated meanings, and R.sup.1 is hydrogen or chlorine or trifluoromethyl, nitro or C.sub.1-3 -alkyl, and R.sup.2 is chlorine or trifluoromethyl, nitro or C.sub.1-3 -alkyl, or R.sup.1 and R.sup.2 together are straight-chain C.sub.3-5 -alkylene or an aromatic ring.
The following examples may be mentioned of radicals A--X in position 2 of the abovementioned 1,2,4-triazolo[1,5-c]quinazolin-5-ones:
acetyl, 2-propionyl, 3-propionyl, 4-buturyl, 3-buturyl, 2-buturyl, 5-valeryl, 4-valeryl, 3-valeryl and their methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl, heptyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl esters in each case or their amides such as methylamides, dimethylamides, ethylamides, diethylamides, propylamides, butylamides and benzylamides;
hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxypropyl, 2-hydroxypropyl, 3-hydroxypropyl, 1-hydroxybutyl, 2-hydroxybutyl, 3-hydroxybutyl, 4-hydroxybutyl, hydroxypentyl, hydroxyheptyl;
methoxymethyl, 1-methoxypropyl, 2-methoxypropyl, 3-methoxypropyl, methoxybutyl, ethoxymethyl, 1-ethoxypropyl, 2-ethoxypropyl, 3-ethoxypropyl, ethoxybutyl, oxomethyl, 1-oxoethyl, 2-oxoethyl, 1-oxopropyl, 2-oxopropyl, 3-oxopropyl, 1-oxobutyl, 2-oxobutyl, 3-oxobutyl, 4-oxobutyl, 1-oxopentyl, 2-oxopentyl, 3-oxopentyl, 4-oxopentyl, cyanomethyl, 1-cyanoethyl, 1-cyanopropyl, 2-cyanopropyl, 3-cyanopropyl, 1-cyanobutyl, 2-cyanobutyl, 3-cyanobutyl, 4-cyanobutyl.
The following may be mentioned as basic structure without the substituents AX:
10-Chloro-1,2,4-triazolo[1,5-c]quinazolin-5-one
8-Chloro-1,2,4-triazolo[1,5-c]quinazolin-5-one
7-Chloro-1,2,4-triazolo[1,5-c]quinazolin-5-one
8,10-Dichloro-1,2,4-triazolo[1,5-c]quinazolin-5-one
10-Bromo-1,2,4-triazolo[1,5-c]quinazolin-5-one
9-Bromo-1,2,4-triazolo[1,5-c]quinazolin-5-one
8-Bromo-1,2,4-triazolo[1,5-c]quinazolin-5-one
7-Bromo-1,2,4-triazolo[1,5-c]quinazolin-5-one
8,10-Dibromo-1,2,4-triazolo[1,5-c]quinazolin-5-one
10-Iodo-1,2,4-triazolo[1,5-c]quinazolin-5-one
9-Iodo-1,2,4-triazolo[1,5-c]quinazolin-5-one
8-Iodo-1,2,4-triazolo[1,5-c]quinazolin-5-one
7-Iodo-1,2,4-triazolo[1,5-c]quinazolin-5-one
8,10-Diiodo-1,2,4-triazolo[1,5-c]quinazolin-5-one
10-Iodo-8-chloro-1,2,4-triazolo[1,5-c]quinazolin-5-one
9-Trifluoromethyl-1,2,4-triazolo[1,5-c]quinazolin-5-one
9-Trifluoromethyl-8-nitro-1,2,4-triazolo[1,5-c]quinazolin-5-one
9-Trifluoromethyl-8-methanesulfonyl-1,2,4-triazolo[1,5-c

REFERENCES:
patent: 4053600 (1977-10-01), Hardtmann et al.
patent: 4128644 (1978-12-01), Vogt
patent: 4463007 (1984-07-01), Schlecker et al.
patent: 5153196 (1992-10-01), McQuaid et al.
J. Med. Chem. (1991), 34, 281-290, Francis et al., Synthesis and Benzodiazepine Binding . . . .

Affiliated with

Also associated with

Rating

Triazoloquinazolines, their preparation and use does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Triazoloquinazolines, their preparation and use, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Triazoloquinazolines, their preparation and use will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-1724098