Beta-lactams

Details Beta-lactams Beta-lactams

C - Chemistry, Metallurgy

07

D

C07D 471/16 (2006.01) A61K 31/435 (2006.01) A61K 31/495 (2006.01) A61K 31/535 (2006.01) A61K 31/54 (2006.01) C07D 498/16 (2006.01) C07D 513/16 (2006.01) C07D 519/00 (2006.01)

Patent

CA 2143519

.beta.-Lactams are described, namely of the general formula Image I in which Z signifies methylene, oxygen or sulphur and R signifies hydrogen, lower (cyclo)alkyl optionally sub- stituted by carboxy, lower alkoxycarbonyl, carbamoyl, lower alkylcarbamoyl, phenylcarbamoyl or hydroxyphenyl- carbamoyl, lower alkenylmethyl, lower alkenylmethoxy- carbonyl, formyl, lower (cyclo)alkanoyl or (cyclo)alkyl- sulphonyl optionally substituted by halogen, cyano, carbamoyl-lower-alkoxy, carbamoyl-lower alkylthio or carbamoyl-lower alkylamino, carbamoyl optionally substituted by lower (cyclo)alkyl, lower alkoxycarbonyl- lower alkyl, benzyloxycarbonyl-lower alkyl or carboxy- lower alkyl or a ring structure of the general formulae Q-X-CO- (a1) Q-X-SO2- (a2) wherein Q represents a 5- or 6-membered ring optionally containing nitrogen, sulphur and/or oxygen and X represents a direct bond or one of the groups -CH2-, -CH2CH2-, -CH=CH-, -NH-, -NHCH2-, -CH2NH-, -CH(NH2)-, -CH2CH2NH-, -C(=NOCH3)-, -OCH2- and -SCH2-; and wherein further A signifies lower alkyl, hydroxy-lower alkyl, vinyl, cyano- vinyl, lower alkoxy, optionally phenyl-substituted lower (cyclo)alkanoyloxy or (cyclo)alkylsulphonyloxy, optionally lower-(cyclo)alkyl-substituted benzoyloxy or phenyl- sulphonyloxy, a residue -S-Het or -S-CH2-Het, wherein Het represents a 5- or 6-membered heterocycle containing nitrogen, sulphur and/or oxygen, or a residue -CH2-L, wherein L represents optionally phenyl-substituted lower (cyclo)alkanoyloxy or (cyclo)alkylsulphonyloxy, optionally lower (cyclo)alkyl-substituted benzoyloxy or phenyl- sulphonyloxy, carbamoyloxy, lower (cyclo)alkoxycarbonyl, carboxy, azido, amino, lower (cyclo)alkanoylamino, lower (cyclo)alkylsulphonylamino, lower (cyclo)alkylamino, di- lower (cyclo)alkylamino, a 5- or 6-membered ring bonded to a nitrogen atom or a residue -S-Het or -S-CH2-Het, wherein Het has the above significance, and pharmaceutically compatible, readily hydrolyzable esters and salts of these compounds. A process for the manufacture of the .beta.-lactams described above as well as intermediates occurring therein are also described, as are corresponding medicaments. The products have .beta.-lactamase inhibiting properties and are useful in the control of .beta.-lactamase-forming pathogens in combination with .beta.-lactam antibiotics. They also exhibit antibacterial activity of their own and can accordingly be used themselves in the control of infectious diseases.

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