Patent GB-1099043-A (GB)
Title: Substituted triazoles and their preparation
IPC: C07D249/14
Filed: 1965-08-04
Abstract: The invention comprises compounds of the formula <FORM:1099043/C2/1> where X is O or S, R1 is methyl, R2 is C1- 6 alkyl, C2- 6 alkenyl, C2- 6 alkoxyalkyl, C1- 6 hydroxyalkyl, C2- 6 methylalkylamino, C2- 8 alkylaminoalkyl, carbalkoxyalkyl of 1-4 C in alkoxy and 1-6 C in alkyl, N-substituted or unsubstituted carbamylalkyl of 1-6 C in alkyl and 1-5 C in the carbamyl moiety, or C2- 7 cyanoalkyl, or R1 and R2 together with the nitrogen atom represent a heterocyclic ring which is morpholino, pyrrolidyl, piperidyl, dehydropiperidyl, 3 - azabicyclo(3.2.2)nonyl, a monosubstituted ring of formula <FORM:1099043/C2/2> where Y1 is H or methyl, Y2 is H, methyl, ethyl or -COOR3 (where R3 is C1- 4 alkyl), and Y3 is H, OH, C1- 9 alkyl, C4- 9 cycloalkyl-alkyl, C1- 9 hydroxyalkyl, C2- 9 alkoxyalkyl, diethylcarbamylethyl carbethoxyethyl, CF3, - COOR3, -CONR4R5 (where R4 and R5 are H or C1- 4 alkyl), C2- 5 carboxyalkyl, dialkylaminoalkyl of up to 8 C, pyrrolidinomethyl, or C7- 9 aralkyl, two of Y1, Y2 and Y3 being hydrogen, or a disubstituted ring of formula <FORM:1099043/C2/3> where Y2 and Y3 are as defined above; and R6 is H, halogen, C1- 4 alkyl, C1- 4 alkoxy, -COOH or -CONH2; and their production by (1) reacting a compound <FORM:1099043/C2/4> (a) with Y.CX.NR1R2, where Y is halogen; (b) with an alkali metal hydride and then with Y.CX.NR1R2; or (c) simultaneously with XCY2 and HNR1R2; (2) reacting a compound <FORM:1099043/C2/5> with HNR1R2; or (3) reacting a corresponding 3-amino compound with formic acid.  3 - Formamido - 1,2,4 - triazole was prepared from 3-amino-1,2,4-triazole and formic acid.  4-n-Propylpiperidinocarbonyl chloride was obtained from 4-n-propylpiperidine and COCl2.  The compounds of the invention are of medicinal value (see Division A5).ALSO:Pharmaceutical compositions comprise at most 5% by weight of a compound of formula <FORM:1099043/A5-A6/1> where X is O or S, R1 is methyl, R2 is C1-6 alkyl, C2-6 alkenyl, C2-6 alkoxyalkyl, C1-6 hydroxyalkyl, C2-6 methylalkylamino, C2-8 alkylaminoalkyl, carbalkoxyalkyl of 1-4C in alkoxy and 1-6C in alkyl, N-substituted or unsubstituted carbamylalkyl of 1-6C in alkyl and 1-5C in the carbamyl moiety, or C2-7 cyanoalkyl, or R1 and R2 together with the nitrogen atom represent a heterocyclic ring which is morpholino, pyrrolidyl, piperidyl, dehydropiperidyl, 3-azobicyclo(3,2,2)nonyl, a monosubstituted ring of formula <FORM:1099043/A5-A6/2> where Y1 is H or methyl, Y2 is H, methyl, ethyl or -COOR3 (where R3 is C1-4 alkyl), and Y3 is H, OH, C1-9 alkyl, C4-9 cycloalkyl, alkyl, C1-9 hydroxyalkyl, C2-9 alkoxyalkyl, diethyl carbamylethyl, carbethoxyethyl, CF3, -COOR3, -CONR4R5 (where R4 and R5 are N or C1-4 alkyl), C2-5 carboxyalkyl, dialkylaminoalkyl of up to 8C, pyrrolidinomethyl or C7-9 aralkyl, two of Y1, Y2 and Y3 being hydrogen; or a disubstituted ring of formula <FORM:1099043/A5-A6/3> where Y2 and Y3 are as defined above; and R6 is H, halogen, C1-4 alkyl, C1-4 alkoxy, -COOH or -CONH2 (see Division C2); together with a non-toxic pharmaceutical carrier therefor.  The compounds of the above formula are analgesics and anti-inflammatory agents.  The compositions may be solutions, suspensions, syrups, elixirs, tablets, capsules or powder packets, and may be administered orally, parenterally or by other methods.  Other pharmaceutically active compounds may be present, e.g. vitamins, pain-killers, tranquilisers, antibiotics and antitussive agents, and also colouring agents, sweetening or other flavouring agents, and solubilising agents.