(Nitrofuryl)pyrazoles, their synthesis and use, and compositions containing them
AssigneeByk Gulden Lomberg Chemische Fabrik GmbH
InventorGeorg Rainer
Life of this patent
Estimating the term…
Abstract
3-(5-Nitro-2-furyl)pyrazoles unsubstituted in the 5-position and 5-(5-nitro-2-furyl)pyrazoles unsubstituted in the 3-position are antimicrobials and disinfectants. The compounds are structurally represented by one of the formulae: ##STR1## wherein A is --CHO, --CN, --COOH, a protected or derived aldehyde group or a protected or derived carboxylic acid group; B is 5-nitro-2-furyl; R.sup.1 is --H, substituted or unsubstituted hydrocarbyl (saturated or unsaturated; acyclic, alicyclic or aromatic; or araliphatic); substituted or unsubstituted (cycloaliphatic or aromatic) heterocyclic or acyl (carboxylic or carbonic acid); R.sup.2 is --H; and n is a positive whole number of at most 2.
Claims85
An antimicrobially-active pyrazole, the pyrazole ring of which is substituted by 5-nitro-2-furyl on a ring carbon atom ortho to one ring nitrogen atom and is unsubstituted on the ring carbon atom ortho to the other ring nitrogen atom, the pyrazole having the formula:
- ##STR32## wherein R.sup.1 is directly bound to one of the two nitrogen atoms of the pyrazole ring, is heterocycle-free, and is --H, substituted or unsubstituted hydrocarbyl, carboxylic acid acyl or carbonic acid acyl, the hydrocarbyl being saturated or unsaturated, acyclic, alicyclic or aromatic, or araliphatic;
- A is --CN, --CH(.dbd.X), aminol, or --C(.dbd.U)--R.sup.11 ;
- U is .dbd.O, .dbd.S, .dbd.NR.sup.3, .dbd.N--O--R.sup.4 or .dbd.N--N(R.sup.7).sub.2 ;
- X is .dbd.O, .dbd.S, .dbd.N--R.sup.3, .dbd.N--O--R.sup.4, .dbd.N--N(R.sup.5)R.sup.6, {--O--(lower)-alkyl}.sub.2, {-S-(lower)alkyl}.sub.2, --O--Y--O-- or --S--Y--S--;
- Y is lower alkylene with from 2 to 5 carbon atoms and optionally substituted by alkyl with from one to 5 carbon atoms;
- Z is .dbd.O, .dbd.S or .dbd.NH;
- R.sup.3 is one of the meanings of R.sup.1 ;
- R.sup.4 is --H, alkanoyl with from 1 to 7 carbon atoms or aroyl;
- R.sup.5 is --H or optionally-substituted alkyl;
- R.sup.6 is one of the meanings of R.sup.7 or --C(.dbd.Z)--N(R.sup.7)R.sup.8 ;
- each of
- R.sup.7 and R.sup.8 is, independently, --H, optionally-substituted alkyl, organic acyl or optionally-substituted aryl;
- R.sup.11 is --OH, alkoxy with from 1 to 11 carbon atoms, aryloxy with up to 12 carbon atoms, aralkoxy with up to 14 carbon atoms, halo, acyloxy, mercapto, azido, --N(R.sup.12)R.sup.13, substituted or unsubstituted hydroxylamino or --NH--N(R.sup.14)R.sup.15 ;
- each of
- R.sup.12 and R.sup.13 is, independently, --H, alkyl having from one to 7 carbon atoms or hydroxyalkyl having from one to 7 carbon atoms;
- each of
- R.sup.14 and R.sup.15, independently, has one of the meanings of R.sup.7 ;
- and
- B is 5-nitro-2-furyl.
An antimicrobially-active pyrazole, the pyrazole ring of which is substituted by 5-nitro-2-furyl on a ring carbon atom ortho to one ring nitrogen atom and is unsubstituted on the ring carbon atom ortho to the other ring nitrogen atom;
- the remaining ring carbon atom bearing a non-heterocyclic substituent selected from the group consisting of --CN, ##STR34## wherein D is .dbd.O, .dbd.S, .dbd.NR.sup.3, .dbd.NOR.sup.4 or .dbd.N--N(R.sup.5)R.sup.6;
- R.sup.3 is --H, substituted or unsubstituted hydrocarbyl, carboxylic acid acyl or carbonic acid acyl;
- any substituent of substituted aliphatic hydrocarbyl being halo, hydroxyl, lower alkoxy, acyloxy or aryloxy;
- any substituent of substituted aromatic hydrocarbyl being halo, lower alkyl, lower alkoxy, lower alkymercapto, trifluoromethyl, nitro, cyclohexyl or phenyl;
- any nuclear substituent of aralkyl or aralkenyl hydrocarbyl being halo, lower alkyl, lower alkoxy, lower alkylmercapto, trifluoromethyl, nitro, cyclohexyl or phenyl;
- any non-nuclear substituent of aralkyl or aralkenyl hydro being halo, hydroxyl, lower alkoxy, acyloxy or aryloxy;
- any substituent of substituted alkanoic carboxylic acid acyl or of substituted alkanoic carbonic acid acyl being hydroxyl, lower alkoxy, mono(lower)alkylamino, dialkylamino or aryl;
- any nuclear substituent of substituted aromatic carboxylic acid acyl or of substituted aromatic carbonic acid acyl being halo, hydroxyl, lower alkyl, lower alkoxy or nitro;
- and any substituent of substituted cycloaliphatic hydrocarbyl being alkyl having from 1 to 4 carbon atoms, any substituted cycloaliphatic bearing at most two substituents;
- R.sup.4 is --H, alkanoyl with from 1 to 7 carbon atoms or aroyl;
- R.sup.5 is --H or optionally-substituted alkyl;
- any substituent of substituted alkyl being halo, hydroxyl, lower alkoxy, acyloxy or aryloxy;
- R.sup.6 is one of the meanings of R.sup.7 or C(.dbd.Z)--N(R.sup.7)R.sup.8 ;
- each of R.sup.7 and R.sup.8 is, independently, -H, optionally-substituted alkyl, organic acid acyl or optionally-substituted aryl;
- any substituent of optionally-substituted alkyl being halo, hydroxyl, lower alkoxy, acyloxy or aryloxy;
- and any substituent of optionally-substituted aryl being halo, lower alkyl, lower alkoxy, lower alkylmercapto, trifluoromethyl, nitro, cyclohexyl or phenyl;
- Z is .dbd.O, .dbd.S or .dbd.NH;
- E is .dbd.S, .dbd.O, .dbd.NR.sup.3, .dbd.N--O--R.sup.4 or .dbd.N--N(R.sup.7).sub.2 ;
- G is --OH, halo, acyloxy, mercapto, azido, --N(R.sup.12)R.sup.13 or --NH--N(R.sup.14)R.sup.15 ;
- each of R.sup.12 and R.sup.13 is, independently, -H or alkyl having from 1 to 7 carbon atoms and optionally-substituted by --OH;
- each of R.sup.14 and R.sup.15 is, independently, one of the meanings of R.sup.7 ;
- M is di(lower)alkoxy or di(lower)alkylmercapto;
- Q is alkoxy with from 1 to 11 carbon atoms, aryloxy with up to 12 carbon atoms or aralkoxy with up to 14 carbon atoms;
- and
- one of the ring nitrogen atoms being additionally bound to a nonheterocyclic member which, independently, has one of the meanings of R.sup.3.
Dependencies are inferred from the claim text.