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US 6,440,957 B1Granted
Cephalosporines having cyclic aminoguanidine substituents as antibiotics
AssigneeBiochemie Gesellschaft m.b.H.
InventorsGerd Ascher, Werner Heilmayer, Johannes Ludescher, Johannes Hildebrandt, Michael Schranz, Josef Wieser
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Abstract
A compound useful as an anti-bacterial agent, having the formula wherein R2 together with the nitrogen atom to which it is attached forms a cyclic aminoguanidine group or derivative thereof as defined
Claims8
A compound of formula
- wherein
- W denotes CH or N,
- V denotes CH or NO,
- R1 denotes hydrogen, (C1-12)acyl, carboxyl or alkyl,
- R3 denotes hydrogen or an ester moiety or a cation,
- R2 denotes a group of formula
- wherein
- X and Y independently of each other each denote (C2-5)alkylene, or
- (C2-5)alkenylene wherein one —C═C— double bond is present, or, in case of at least C4-alkenylene, wherein two —C═C— double bonds are present,
- R4 denotes hydrogen or alkyl,
- R5 denotes hydrogen, alkyl, or aminoiminomethyl,
- R6 denotes hydrogen, alkyl, cycloalkyl, amino, hydroxy, alkoxy, unsaturated or saturated heterocyclyl having 5 or 6 ring members and 1 or 2 hetero atoms and being unsubstituted or substituted by alkyl, aryl, alkoxy, halogen, hydroxy, carboxyl, —SO3H, C(1-12)-acyl, amino, guanidino, oxo, thiono, mercapto, alkylthio, arylthio, imino or alkylimino, or R6 denotes a group of formula —N═CHR8, wherein
- R8 denotes alkyl, aryl or unsaturated or saturated heterocyclyl having 5 or 6 ring members and 1 or 2 hetero atoms and being unsubstituted or substituted by alkyl, aryl, alkoxy, halogen, hydroxy, carboxyl, —SO3H, C(1-12)-acyl, amino, guanidino, oxo, thiono, mercapto, alkylthio, arylthio, imino or alkylimino, or
- R5 and R6 together with the nitrogen atoms to which they are attached denote unsaturated or saturated heterocyclyl having 5 or 6 ring members and 1 or 2 hetero atoms and being unsubstituted or substituted by alkyl, aryl, alkoxy, halogen, hydroxy, carboxyl, —SO3H, C(1-12)-acyl, amino, guanidino, oxo, thiono, mercapto, alkylthio, arylthio, imino or alkylimino,
- R′6 denotes alkyl,
- R7 denotes hydrogen, or
- R6 and R7 together with the nitrogen atom to which they are attached form unsaturated or saturated heterocyclyl having 5 or 7 ring members and 1 or 2 hetero atoms and being unsubstituted or substituted by alkyl, aryl, alkoxy, halogen, hydroxy, carboxyl, —SO3H, C(1-12)-acyl, amino, guanidino, oxo, thiono, mercapto, alkylthio, arylthio, imino or alkylimino.
14 more elements
A compound of formula
- wherein
- Wp denotes CH or N,
- Vp denotes ═CH— or ═N—O—,
- R1p denotes hydrogen, C(1-12)-acyl, carboxyl, unsubstituted alkyl, or alkyl substituted by halogen or carboxyl,
- R3p denotes hydrogen, an ester forming group or a cation,
- R2p denotes a group of formula
- wherein Xp and Yp are the same or different and each denote a —(CH2)n-group, wherein n denote a number from 2 to 5, and optionally two CH2-groups are replaced by a —CH═CH— group and optionally one or more hydrogen atoms are replaced by halogen, alkyl, cycloalkyl, hydroxyalkyl, aminoalkyl, carboxyl or ethoxycarbonyl,
- R4p denotes hydrogen, alkyl or hydroxyalkyl,
- R5p denotes hydrogen, alkyl, (poly)hydroxyalkyl or aminoalkyl, wherein optionally the alkyl groups are additionally substituted by —COOH, —SO3H, or —OPO3H2,
- R6p denotes hydrogen, alkyl, hydroxyalkyl, aminoalkyl, amino, hydroxy, alkoxyalkyl, cycloalkyl, a group N═CHR8p, wherein
- R8p denotes aryl or heteroaryl, or a group —NR9pR10p, wherein R9p and R10p are the same or different and each denote hydrogen, alkyl, hydroxyalkyl or aryl or denote together with the nitrogen atom a saturated, unsubstituted heterocycle with 5 or 6 ring members with one or two nitrogen and/or oxygen atoms, and
- R7p denotes hydrogen, or
- R7p and R6p denote together with the nitrogen atom a heterocycle with 5 to 7 ring members containing one or two nitrogen and/or oxygen atoms, in free form, or, where such forms exist, in the form of salts or hydrates thereof.
10 more elements
7-{[(5-Amino-1,2,4-thiadiazole-3-yl)-(Z)-(fluoromethoxyimino)acetyl]amino}-3-{[(3-ethyl-2-methylimino-imidazolidine-1-yl)imino]methyl}-3-cephem-4-carboxylic acid.
Dependencies are inferred from the claim text.