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US 2004/0110963 A1Published application
Novel hydrazones
OwnerKaspar Burri, Johannes Hoffner +2inventors
InventorsKaspar Burri, Johannes Hoffner, Khalid Islam, Seema Mukhija
Life of this patent
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Abstract
The invention relates to novel hydrazone derivatives and their use as active ingredients in the preparation of pharmaceutical compositions. The invention also concerns related aspects including processes for the preparation of the compounds, pharmaceutical compositions containing one or more of those compounds and especially their use as anti-infectives.
Claims15
Compounds of the general formula 1,
- 6
- wherein R1 represents lower alkyl-carbonylamino;
- formylamino;
- amino;
- hydroxy;
- R2 represents hydrogen;
- hydroxy;
- lower alkyl;
- fluoro;
- chloro;
- R3 represents hydrogen;
- methyl;
- ethyl;
- isopropyl;
- R11 represents hydrogen;
- hydroxy;
- lower alkyl;
- lower alkoxy;
- fluoro;
- chloro;
- amino;
- R12 represents hydrogen;
- hydroxy;
- lower alkyl;
- lower alkoxy;
- fluoro;
- chloro;
- amino
- R13 represents hydrogen;
- lower alkyl
- R4 represents aryl;
- arylmethyl;
- indoyl methyl;
- mono-, di- or triN′- substituted aryl, arylmethyl, which substituents may lower alkyl, hydroxy, lower alkoxy, fluoro, chloro, bromo, trifluoromethyl, amino, lower alkylamino, lower alkylendioxy, N-pyrrolyl, 2-pyrrolyl, 3, pyrrolyl and which substituents may be the same or different;
- in case R1 represents amino and R2, R11, R12, R13 and R3 represent hydrogen, R4 is not unsubstituted phenyl;
- phenylmethyl;
- 2-amino-phenyl;
- 2-hydroxy-phenyl;
- 4-chloro-phenyl;
- in case R1 represents amino and R2, R11, R12 and R13 represent hydrogen and R3 represents methyl, R4 is not unsubstituted phenyl;
- 2-hydroxy-phenyl;
- in case R1 represents methyl-carbonylamino and R2, R3, R11, R13 and R12 represent hydrogen, R4 is not 4-hydroxy-3-methoxy-phenyl;
- in case R1 is hydroxy and R2, R11, R12 and R13 represent hydrogen and R3 represents methyl, R4 is not unsubstituted phenyl;
- 4-methyl-phenyl;
- 2-methyl-phenyl;
- 2-hydroxy-phenyl;
- 4-methoxy-phenyl;
- 4-chloro-phenyl;
- 2-chloro-phenyl;
- 2,4,6-trimethyl-phenyl;
- in case R1 is hydroxy and R2, R11, R12 and R13 represent hydrogen and R3 represents ethyl, R4 is not unsubstitued phenyl or 2-hydroxy-phenyl;
- in case R1 is hydroxy and R2, R11, R12 and R3 represent hydrogen and R13 represents methyl, R4 is not unsubstituted phenyl;
- in case R1 is hydroxy and R2, R11, R12, R13 and R3 represent hydrogen, R4 is phenyl substituted with 2-trifluoromethyl, 3-trifluoromethyl, 3-methoxy or (2-amino-5-chloro);
- in case R1 and R11 represent hydroxy and R2, R3, R12 and R13 represent hydrogen, R4 is not 2-chloro-phenyl;
- in case R1 is hydroxy and R11 is methoxy and R2, R3, R12 and R13 represent hydrogen, R4 is not unsubstituted phenyl;
- 2-hydroxy-phenyl;
- 2-chloro-phenyl;
- 4-hydroxy-3-methoxy-phenyl;
- 5-chloro-2-hydroxy-phenyl;
- 2-(3-hydroxy)-naphthyl;
- 2,4-dichloro-phenyl;
- 4-amino-3,5-dichloro-phenyl;
- 5-bromo-2-hydroxy-phenyl;
- in case R1, R11 and R12 represent hydroxy and R2 and R13 represent hydrogen and R3 is methyl, R4 is not unsubstituted phenyl;
- in case R1 and R12 represent hydroxy and R2, R3, R11 and R13 represent hydrogen, R4 is not unsubstituted phenyl;
- 2-hydroxy-phenyl;
- 4-methoxy-phenyl;
- 4-hydroxy-3-methoxy-phenyl;
- 2,4-dichloro-phenyl;
- in case R1 and R12 represent hydroxy and R2, R11 and R13 represent hydrogen and R3 is methyl, R4 is not unsubstituted phenyl;
- 2-hydroxy-phenyl;
- in case R1 is hydroxy and R12 is methoxy and R2, R3, R11 and R13 represent hydrogen, R4 is not 4-hydroxy-3-methoxy-phenyl;
- in case R1 is hydroxy and R12 is methoxy and R2, R11 and R13 represent hydrogen and R3 is methyl, R4 is not unsubstituted phenyl;
- in case R1 is hydroxy and R2 is chloro and R3, R11, R12 and R13 represent hydrogen, R4 is not unsubstituted phenyl;
- 2-methyl-phenyl;
- 2-hydroxy-phenyl;
- 4-hydroxy-phenyl;
- 4-methoxy-phenyl;
- 4-chloro-phenyl;
- 5-chloro-2-hydroxy-phenyl;
- 2-hydroxy naphth-1-yl;
- 3-hydroxy naphth-2-yl;
- 2,4-dichloro-phenyl;
- 3,4-dichloro-phenyl;
- 3,4,5-trihydroxy-phenyl;
- 5-bromo-2-hydroxy-phenyl;
- in case R1 is hydroxy and R2 and R11 represent chloro and R3, R12 and R13 represent hydrogen, R4 is not 2-hydroxy-phenyl;
- 5-chloro-2-hydroxy-phenyl;
- 3-hydroxy-naphth-2-yl;
- 2-hydroxy-3,5-dichloro-phenyl;
- 5-bromo-2-hydroxy-phenyl;
- 3,5-dibromo-2-hydroxy-phenyl;
- N-pyrrolyl;
- in case R1 is hydroxy and R2 and R3 represent methyl and R11, R12 and R13 represent hydrogen, R4 is not unsubstituted phenyl;
- in case R1 is hydroxy and R2 is methyl and R3, R11, R12 and R13 represent hydrogen, R4 is not 4-chloro-phenyl;
- 2-naphthyl;
- 2-bromo-phenyl;
- 3-bromo-phenyl;
- 4-bromo-phenyl;
- in case R1 is hydroxy and R2 is fluoro and R11, R12 and R13 represent hydrogen and R3 is methyl or ethyl, R4 is not 4-fluoro methyl;
- in case R1 and R12 represent hydroxy and R11 is chloro and R3 and R13 represent hydrogen and R2 is n-butyl or (3-methyl)-butyl or n-pentyl, R4 is not 4-amino-2-hydroxy-phenyl;
- in case R1 and R12 represent hydroxy and R2 is ethyl or n-butyl or n-hexyl or (3-methyl)-butyl and R3, R11 and R13 represent hydrogen, R4 is not unsubstituted phenyl, 4-amino-phenyl, 4-hydroxy-phenyl, 2-hydroxy-phenyl, 4-amino-2-hydroxy-phenyl,
- and pharmaceutically acceptable salts thereof.
100 more elements
Compounds of the formulae 2a-2e,
- 7
- wherein R3, R13 and R4 have the meaning given in formula 1 and R14 is hydrogen, lower alkyl , formyl or acetyl and R16 is hydrogen, methyl, fluoro, chloro, hydroxy or ethyl and pharmaceutically acceptable salts thereof.
Compounds of the formulae 3a-3e,
- 8
- wherein R4 has the meaning given in formula 1 and R14 is hydrogen, lower alkyl formyl or acetyl and R16 is hydrogen, methyl, fluoro, chloro, hydroxy or ethyl and R15 is hydrogen, methyl or ethyl and pharmaceutically acceptable salts thereof.
Compounds of the formulae 4a-f
- 9
- wherein in formula 4a R15 represents hydrogen, methyl or ethyl and, R17, R18, R19, R20 and, R21, which may be the same or different, represent hydrogen, N-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, lower alkyl, hydroxy, lower alkoxy, fluoro, chloro, bromo, trifluoromethyl, amino, lower alkylamino, lower alkylendioxy, in case R15 is methyl either one or two of the substituents R17, R18, R19, R20, R21 represent N-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, lower alkyl, hydroxy, lower alkoxy, fluoro, chloro, bromo, trifluoromethyl, amino, lower alkylamino, lower alkylendioxy or
- wherein in formula 4b R15 represents hydrogen, methyl or ethyl and R17, R18, R19, R20 and R21, which may be the same or different, represent hydrogen, N-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, lower alkyl, hydroxy, lower alkoxy, fluoro, chloro, bromo, trifluoromethyl, amino, lower alkylamino, lower alkylendioxy, in case R17 is N-pyrrolyl either one or two of the substituents R18, R19, R20, R21 represent lower alkyl, hydroxy, lower alkoxy, fluoro, chloro, bromo, trifluoromethyl, amino, lower alkylamino, lower alkylendioxy or
- wherein in formula 4c R15 represents hydrogen, methyl or ethyl and R17, R18, R19, R20 and R21, which may be the same or different, represent hydrogen, N-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, lower alkyl, hydroxy, lower alkoxy, fluoro, chloro, bromo, trifluoromethyl, amino, lower alkylamino, lower alkylendioxy, in case R15 is hydrogen and R17 is chloro either one or two of the substituents R18, R19, R20, R21 represents, N-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, lower alkyl, hydroxy, lower alkoxy, fluoro, chloro, bromo, trifluoromethyl, amino, lower alkylamino or lower alkylendioxy or
- wherein in formula 4d R17, R18, R19, R20 and R21, which may be the same or different, represent hydrogen, N-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, lower alkyl, hydroxy, lower alkoxy, fluoro, chloro, bromo, trifluoromethyl, amino, lower alkylamino, lower alkylendioxy, in case R17 is hydrogen or hydroxy, either one or two of the substituents R18, R19, R20, R21 represent N-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, lower alkyl, hydroxy, lower alkoxy, fluoro, chloro, bromo, trifluoromethyl, amino, lower alkylamino, lower alkylendioxy or
- wherein in formula 4e R15 represents hydrogen, methyl, ethyl and R17, R18, R19, R20 and R21, which may be the same or different, represent hydrogen, N-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, lower alkyl, hydroxy, lower alkoxy, fluoro, chloro, bromo, trifluoromethyl, amino, lower alkylamino, lower alkylendioxy or
- wherein in formula 4f R15 represents hydrogen, methyl, ethyl and R17, R18, R19, R20 and R21, which may be the same or different, represent hydrogen, N-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, lower alkyl, hydroxy, lower alkoxy, fluoro, chloro, bromo, trifluoromethyl, amino, lower alkylamino, lower alkylendioxy, in case R15 is hydrogen then at least one of the substituents R17, R18, R19, R20 or R21 represents pyrrolyl, trifluoromethyl, or lower alkylamino
- and pharmaceutically accepable salts thereof.
5 more elements
Compounds of the formula 5a-e,
- 10
- wherein in formula 5a R15 represents hydrogen, methyl or ethyl and R17, R18, R19, R20 and R21, which may be the same or different, represent hydrogen, lower alkyl, hydroxy, lower alkoxy, fluoro, chloro, bromo, trifluoromethyl, lower alkylamino, lower alkylendioxy, with the proviso that one or two of the substituents R17, R18, R19, R20 and R21 represent trifluoromethyl or chloro or
- wherein in formula 5b R15 represents hydrogen, methyl or ethyl and R17, R18, R19, R20 and R21, which may be the same or different, represent hydrogen, lower alkyl, hydroxy, lower alkoxy, fluoro, chloro, bromo, trifluoromethyl, lower alkylamino, lower alkylendioxy, N-pyrrolyl, 2-pyrrolyl or 3-pyrrolyl, with the proviso that one or two of the substituents R17, R18, R19, R20 and R21 represent N-pyrrolyl, 2-pyrrolyl or 3-pyrrolyl, in case R17 represents N-pyrrolyl, at least one of the substituents R18, R19, R20 of R21 represents lower alkyl, hydroxy, lower alkoxy, fluoro, chloro, bromo, trifluoromethyl, lower alkylamino, lower alkylendioxy or
- wherein in formula 5c R15 represents hydrogen, methyl or ethyl and R17, R18, R19, R20 and R21, which may be the same or different, represent hydrogen, lower alkyl, hydroxy, lower alkoxy, fluoro, chloro, bromo, trifluoromethyl, lower alkylamino, lower alkylendioxy, with the proviso that one or two of the substituents R17, R18, R19, R20 and R21 represent chloro or trifluoromethyl or
- wherein in formula 5d R17, R18, R19, R20 and R21, which may be the same or different, represent hydrogen, lower alkyl, lower alkoxy, fluoro, chloro, bromo, trifluoromethyl, amino, lower alkylamino, lower alkylendioxy, with the proviso that one or two of the substituents R17, R18, R19, R20 and R21 represent chloro, methoxy, methyl or trifluoromethyl or
- wherein in formula 5e R15 represents hydrogen, methyl, ethyl and R17, R18, R19, R20 and R21 which may be the same or different, represent hydrogen, N-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, lower alkyl, hydroxy, lower alkoxy, fluoro, chloro, bromo, trifluoromethyl, amino, lower alkylamino, lower alkylendioxy, with the proviso that one or two of the substituents R17, R18, R19, R20 and R21 represent chloro, methoxy, methyl of trifluoromethyl or
- wherein in formula 5f R15 represents hydrogen, methyl, ethyl and R17, R18, R19, R20 and R21, which may be the same or different, represent hydrogen, N-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, lower alkyl, hydroxy, lower alkoxy, fluoro, chloro, bromo, trifluoromethyl, amino, lower alkylamino, lower alkylendioxy, with the proviso that in case R15 is hydrogen at least one of the substituents R17, R18, R19, R20 and R21 represents N-pyrroly, 2-pyrrolyl, 3-pyrrolyl, trifluoromethyl or lower alkylamino
- and pharmaceutically acceptable salts thereof.
5 more elements
The end products as described in Examples 1 to 53 and pharmaceutically acceptable salts thereof.
Dependencies are inferred from the claim text.