Method for producing new chemical compounds

Details Method for producing new chemical compounds Method for producing new chemical compounds

C - Chemistry, Metallurgy

07

D

260/480.1, 260/3

C07D 213/32 (2006.01) C07D 213/38 (2006.01) C07D 213/73 (2006.01) C07D 295/13 (2006.01) C07D 307/14 (2006.01) C07D 307/52 (2006.01) C07D 333/20 (2006.01)

Patent

CA 1077953

ABSTRACT OF THE DISCLOSURE A process is provided for the preparation of a series of new compounds having the general formula I Image (I) in which R1 stands for an unsubstituted or substituted phenoxy, phenylthio, benzyl, phenylsulfinyl, or anilino radical and, where substituted, such substituents are selected from the group consisting of halogen atoms, lower alkyl, halolower alkyl, nitro and amino groups, mono- or dialkylamino or acylamino groups, hydroxy groups, lower alkoxy groups or hydroxy groups esterified with lower aliphatic carboylic acids and lower alkylthio or phen- ylthio radicals; R2 stands for a -YR2' radical, in which Y represents -O-, -S-, or -NH-, and R2' represents C1 - C6 alkyl, C2 - C6-alkenyl or -alkynyl, or methyl or ethyl substituted with phenyl, furyl, thienyl or pyridyl or C1 - C6 alkyl, or C2 - C6- alkenyl or C2 - C6 alkynyl, each of the above substituted by one or more members selected from the group consisting of halogen atoms, lower alkyl, halolower alkyl, nitro and amino groups, mono- or dialkylamino or acylamino groups, hydroxy groups, lower alkoxy groups or hydroxy groups esterified with lower aliphatic carboxylic acids and lower alkylthio or phenylthio radicals; R3 and R4 which can be the same or different, and unsub- stituted or substituted and, where substituted, such substituents are selected from the group consisting of halogen atoms, lower alkyl, halolower alkyl, nitro and amino groups, mono- or dialkylamino or acylamino groups, hydroxy groups, lower alkoxy groups or hydroxy groups esterified with lower aliphatic carboxylic acids and lower alkylthio or phenylthio radicals, stand for hydrogen or for a straight or branched C1-C8-alkyl, C2-C8-alkenyl or -alkynyl radical, a C5-C7-cycloalkyl, a phenyl, or a heterocyclic ring system moiety selected from the group consisting of furyl, thienyl, pyrrolidyl, pyrazolyl, pyrazolinyl, pyrazolidinyl, oxazolyl, thiazolyl, thiadiazolyl, pyridyl, piperidyl, tetrahydropyridazinyl, hexahydropyridazinyl, pyrimidyl, pyra- zinyl, morpholinyl, thiazinyl, perhydroazepinyl, and hexahydro- oxepinyl heterocyclic ring system, or for a C1-C3 alkyl radical substituted with phenyl or with the aforesaid heterocyclic ring system moiety and R4 furthermore stands for a lower carbalkoxy radical a C1-C6 alkanoyl radical, or a benzoyl radical; and salts thereof with pharmaceutically acceptable acids. The compounds so prepared possess a pronounced diuretic and/or saluretic activity with a very low excretion of potassium ions. The low toxicity also makes the present compounds particularly valuable in human and veterinary practice.

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