AT315840B - Process for the preparation of new nitrofuryl- or nitrothienyl-triazolo [4,3-b] pyridazine derivatives - Google Patents

Description

  

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   The invention relates to a process for the preparation of new triazolo 4, 3-b] pyridazine derivatives of the general formula
 EMI1.1
 or.
 EMI1.2
 in which X is an oxygen or sulfur atom, Rl and R2 a cycloalkyl radical with 5 to 7 carbon atoms or an alkyl or alkenyl group, which is optionally substituted by phenyl, hydroxyl, mercapto,
 EMI1.3
 Amido groups can be substituted, where the two radicals Rl and Rz together with the nitrogen atom can also form a piperidine, piperazine, pyrrolidine or morpholine ring optionally substituted by a hydroxyl, carboxyl, alkyl or hydroxyalkyl group and where optionally one of the radicals R and Rz can also be hydrogen,

   as well as their pharmacologically acceptable salts.



   Nitrofuryl-triazolc 4, 3-b] pyridazine derivatives which are substituted by an optionally acylated amino group and have antimicrobial properties, in particular antibacterial activity in the urine, are known from the German Offenlegungsschrift 1670095.

   It has now been found that the urinary activity of nitrofuryl-triazolo 4, 3-b] pyridazine derivatives can be increased to an unexpected and surprising extent for the person skilled in the art if the above-mentioned amino group is substituted with variable alkyl radicals.
 EMI1.4
 
 EMI1.5
 
 EMI1.6
 
 EMI1.7
 
 EMI1.8
 If desired, subsequently converted into their physiologically tolerable salts and / or in the compounds I obtained the substituents Rl and / or Rz are converted into other substituents Rl or Rz of the above meaning.
 EMI1.9
 



   The new compounds have particularly interesting antimicrobial properties, especially with respect to Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa and Proteus mirabilis. Since these compounds surprisingly have an extremely high antibacterial activity in the urine, they are outstandingly suitable for the treatment of urinary tract infections, which is also noteworthy the low toxicity of the compounds L
The reactive derivative of the aldehydes III is used, for. B. diacyl derivatives, preferably diacetates, wel-

 <Desc / Clms Page number 2>

 
 EMI2.1
 

** WARNING ** End of DESC field may overlap beginning of CLMS **.

 

Claims (1)

EMI2.2 or. <Desc / Clms Page number 3> EMI3.1 EMI3.2 men or an alkyl or alkenyl group which can optionally be substituted by phenyl, hydroxyl, mercapto, lower alkoxy, lower alkyl mercapto, morpholino, furyl or, optionally alkylated, amino or amido groups, both of which Radicals R, and Rz together with the nitrogen atom can also form a piperidine, piperazine, pyrrolidine or morpholine ring optionally substituted by a hydroxyl, carboxyl, alkyl or hydroxyalkyl group, and optionally one of the EMI3.3 EMI3.4 EMI3.5 EMI3.6 as well as of their pharmacologically acceptable salts, in which X has the meaning given above, or condensed with a reactive derivative thereof and, if desired, then converted into their physiologically tolerable salts and / or in the compounds I obtained converts the substituents Rl and / or R into other substituents Rl or Rz of the above meaning. 2. The method according to claim 1, characterized in that starting materials of the formula (II) are used in which R1 and R2 are a cycloalkyl radical having 5 to 7 carbon atoms or an alkyl EMI3.7 can form hydroxyl, carboxyl, alkyl or hydroxyalkyl group-substituted piperidine, piperazine, pyrrolidine or morpholine ring and where one of the radicals R1 and R2 can optionally also be hydrogen, 3. VerfahrennachAnspruch2, characterized in that starting materials of the formula (II) are used in which the hydrocarbon radicals R1 and R2 are substituted by longer alkyl, phenyl or acylamino groups.