Lincomycin derivatives possessing antibacterial activity

A compound of the following formula (I):

• wherein:
• W is a nitrogen-containing ring:
• wherein m is 0,1,2, or 3;
• wherein when m is 2, the nitrogen-containing ring may optionally contain a double bond between the 4 and 5 nitrogen-containing ring positions;
• wherein when m is 3, the nitrogen-containing ring may optionally contain one double bond between either the 4 and 5 nitrogen-containing ring positions or between the 5 and 6 nitrogen-containing ring positions;
• wherein the nitrogen-containing ring positions are consecutively numbered counterclockwise beginning with “1” at the nitrogen;
• R1 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkoxy, substituted alkoxy, halo, alkylsulfanyl, and substituted alkylsulfanyl;
• R2 and R3 are independently hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkoxy, substituted alkoxy, cyano, alkylsulfanyl, substituted alkylsulfanyl, hydroxy, or halo, or one of R2 and R3 is ═NOR7 and the other is absent, wherein R7 is H or alkyl, or one of R2 and R3 is ═CH2 and the other is absent;
• R6 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, iminomethyl, —C(O)O-alkyl, —C(O)O-substituted alkyl, —C(O)O-aryl, —C(O)O-substituted aryl, —C(O)O-heteroaryl, —C(O)O-substituted heteroaryl, —C(O)O-alkylene-cycloalkyl, —C(O)O-alkylene-substituted alkyl, —C(O)O-heterocyclic, —C(O)O-substituted heterocyclic, —[C(O)O]p-alkylene-heterocycle, —[C(O)O]p-alkylene-substituted heterocycle, where p is zero or one, -(carboxamido)alkyl, (carbamoyl)alkyl, 5-alkyl-[1,3]dioxol-2-one-4-yl-methyl, 5-alkyl-[1,3]dioxol-2-one-4-yl-methoxy-carbonyl, or —N(R6)— fragment is part of the amidine, N-cyanoamidine, N-hydroxyamidine, or N-alkoxyamidine structure;
• R9, which can be singly or multiply substituted in the ring on the same or different carbons, is independently selected from the group consisting of alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, alkenyl, substituted alkenyl, alkylidene, substituted oxygen, substituted nitrogen, halogen, aryl, substituted aryl, alkylsulfanyl, substituted alkylsulfanyl, substituted arylsulfanyl, heteroarylsulfanylalkyl, heterocyclicsulfanylalkyl, heteroarylsulfanyl, heterocyclicsulfanyl, azido, alkoxyalkoxy, and —S(O)qR13 where q is an integer equal to zero, one or two and R13 is selected from the group consisting of alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, heterocyclic and substituted heterocyclic, and wherein not more than one —S(O)qR13 group is present on the nitrogen-containing ring;
• or a pharmaceutically acceptable salt thereof,
• with the proviso that when m is 1 or 2 and the nitrogen containing ring has only single bonds, and when R1 is selected from the group consisting of alkylsulfanyl, substituted alkylsulfanyl, alkoxy, and substituted alkoxy, and when R9 is singly substituted on a ring carbon, then R9 is not alkyl or alkylidene.