Substituted N-acyl-N"-(3-amino-2-cyanoacryloyl-)formamidrazones
AssigneeByk Gulden Lomberg Chemische Fabrik GmbH
InventorsKurt Klemm, Erhard Langenscheid
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Abstract
Therapeutically-active and pharmacologically-acceptable N-acyl-N" -(3-amino-2-cyanoacryloyl)-formamidrazones and their pharmaceutically-acceptable acid-addition salts inhibit xanthine oxidase and are useful as the active ingredient in medicaments for the treatment of gout.
Claims27
A therapeutically-active and pharmacologically-acceptable xanthine-oxidase-inhibiting compound selected from the group consisting of (a) an N-acyl-N"-(3-amino-2-cyanoacryloyl)-formamidrazone, (b) a tautomer of (a), and (c) a salt of (a) with an organic or inorganic acid, the acyl of which is hydrocarbylacyl of a carboxylic or carbonic acid having from 1 to 14 carbon atoms, any ring of which has at most 6 ring carbon atoms and any unsaturation of which is aromatic unsaturation.
A compound of the formula ##STR20## wherein R.sup.1 is a member selected from the group consisting of straight- or branch-chained alkyl with from 1 to 7 carbon atoms and cycloalkyl with from 3 to 6 carbon atoms;
- R.sup.2 is --H or one of the meanings of R.sup.1 ;
- or
- R.sup.1 and R.sup.2 together denote (a) pentamethylene or (b) pentamethylene in which at least one methylene is replaced by a member selected from the group consisting of --O--, --S-- and --NR.sup.7 --;
- R.sup.3 is a member selected from the group consisting of CO--R.sup.4, --CO--OR.sup.4 and --CO--N(R.sup.5)R.sup.6
- R.sup.4 is an R.sup.5 (R.sup.6)N-substituted or unsubstituted member selected from the group consisting of straight- or branch-chained alkyl with from 1 to 14 carbon atoms, a methylene (other than a methylene) group of which is optionally replaced by an oxygen atom;
- cycloalkyl with from 3 to 6 carbon atoms;
- phenyl;
- phenyl substituted by at least one member selected from the group consisting of straight- or branch-chained alkyl, alkoxy or alkylmercapto having from 1 to 7 carbon atoms, alkoxycarbonyl with from 2 to 5 carbon atoms, halo, trifluoromethyl, nitro and cyano;
- phenylalkyl, the alkyl of which has from 1 to 6 carbon atoms and the phenyl of which is optionally substituted by at least one member selected from the group consisting of straight- or branch-chained alkyl, alkoxy or alkylmercapto having from 1 to 7 carbon atoms, alkoxycarbonyl with from 2 to 5 carbon atoms, halo, trifluoromethyl, nitro and cyano;
- or a C.sub.3.sub.-6 --cycloalkyl substituted by --N(R.sup.5)R.sup.6 ;
- each of R.sup.5 and R.sup.6 is, independently, a member selected from the group consisting of -H;
- straight- or branch-chained alkyl with from 1 to 7 carbon atoms, a methylene group of which is optionally replaced by an oxygen atom;
- and cycloalkyl with from 3 to 6 carbon atoms;
- or
- R.sup.5 and R.sup.6 together denote alkylene with from 2 to 5 carbon atoms or such alkylene in which at least one methylene group is replaced by --O--, --S-- or --NR.sup.7 --;
- R.sup.7 is a member selected from the group consisting of --H;
- hydroxy-substituted or unsubstituted straight- or branch-chained alkyl with from 1 to 7 carbon atoms;
- and phenyl optionally substituted by straight- or branch-chained alkyl or alkoxy with from 1 to 7 carbon atoms, halo or trifluoromethyl.
A compound according to claim 4 wherein
- R.sup.1 is a member selected from the group consisting of methyl, ethyl and cyclohexyl or, together with R.sup.2, --CH.sub.2 --CH.sub.2 --O--CH.sub.2 --CH.sub.2 -- or --CH.sub.2 --CH.sub.2 --N(R.sup.5)--CH.sub.2 --CH.sub.2 --;
- R.sup.2 is a member selected from the group consisting of methyl, ethyl and cyclohexyl or, together with R.sup.1, --CH.sub.2 --CH.sub.2 --O--CH.sub.2 --CH.sub.2 -- or --CH.sub.2 --CH.sub.2 --N(R.sup.7)--CH.sub.2 --CH.sub.2 --;
- R.sup.4 has the meaning accorded it in claim 31;
- and
- R.sup.7 is a member selected from the group consisting of -H, methyl, ethyl and 2-hydroxyethyl.
Dependencies are inferred from the claim text.